EP3107896A1 - Indole carboxamides and benzimidazole carboxamides as insecticides and acaricides - Google Patents

Indole carboxamides and benzimidazole carboxamides as insecticides and acaricides

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Publication number
EP3107896A1
EP3107896A1 EP15704310.0A EP15704310A EP3107896A1 EP 3107896 A1 EP3107896 A1 EP 3107896A1 EP 15704310 A EP15704310 A EP 15704310A EP 3107896 A1 EP3107896 A1 EP 3107896A1
Authority
EP
European Patent Office
Prior art keywords
spp
compounds
methyl
formula
ethyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP15704310.0A
Other languages
German (de)
French (fr)
Inventor
Markus Heil
Eike Kevin Heilmann
Werner Hallenbach
Kerstin Ilg
Ulrich Görgens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3107896A1 publication Critical patent/EP3107896A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Definitions

  • the present invention relates to novel pesticides, a process for their preparation and their use as active ingredients, in particular their use as insecticides and acaricides.
  • indole-2-carboxamides and benzimidazole-2-carboxamides and their use as drugs see, for example, WO-A-2010/126164, WO-A-2010/054138, US 2009/0041722, WO-A-2007 / 115938, EP1460064, WO-A-2004-A-056768, WO-A-2004/032921, WO-A-20010/32622.
  • WO-A-2012/119984 discloses indole-2-carboxamides and benzimidazole-2-carboxamides and their use as crop protection agents.
  • Example 273 a compound is disclosed which has an aminothiocarbonylcyclopropyl substitution of the amide residue on the indole six-membered ring. However, this compound is only substituted on the phenyl ring with trifluoromethyl.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity.
  • the novel compounds of the formula (I) are notable in particular in that they have an aminothiocarbonylcyclopropyl substitution of the amide radical on the indole six-membered ring and that the phenyl ring is polysubstituted, where at least one of these substituents is halogen.
  • the combination of these features surprisingly leads to improved biological effectiveness. This results from the biological application examples shown.
  • the present invention therefore relates to compounds of the general formula (I)
  • R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, chlorotetrafluoroethyl, difluoromethoxy, trifluoromethoxy, at least one substituent R 1 being fluorine, chlorine, bromine or iodine,
  • R 2 is fluorine, trifluoromethyl or hydrogen.
  • n stands for 2, 3, 4 or 5
  • R 3 is hydrogen
  • R 4 is hydrogen, methyl, ethyl, prop-1-yl, prop-2-en-1-yl, prop-2-yn-1-yl, ethenyl, but-2-yn-1 -yl stands,
  • G is CH or N
  • R 6 represents cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl or trifluoromethyl, and salts and N-oxides of compounds of the formula (I) and their use for controlling animal pests.
  • R 1 is fluorine, chlorine, bromine, iodine or trifluoromethyl, where at least one substituent R 1 is fluorine, chlorine, bromine or iodine,
  • R 2 is fluorine or hydrogen is n 2, 3 or 4, R 3 is hydrogen,
  • R 4 is hydrogen, methyl, ethyl or prop-2-yn-1-yl, G is CH or N,
  • R 6 represents chlorine, bromine, methyl or trifluoromethyl, and salts and N-oxides of compounds of the formula (I) and their use for controlling animal pests.
  • R 1 is fluorine, chlorine, bromine or trifluoromethyl and n is 2, 3 or 4, wherein at least one substituent R 1 is fluorine or chlorine, and all other groups, radicals and substituents have the meaning given above for the preferred embodiment (2-1).
  • R 6 is chlorine or methyl, all other groups, radicals and substituents being those described above for the preferred embodiment (2-1) or the above for the particularly preferred embodiment (3-1 ).
  • G is CH, with all other groups, radicals and substituents as described above for the preferred embodiment (2-1) or the above for the particularly preferred embodiment (3-1) or the have the meaning given above for the particularly preferred embodiment (3-2).
  • G is N, where all other groups, radicals and substituents are those described above for the preferred embodiment (2-1) or the above for the particularly preferred embodiment (3-1) or the have the meaning given above for the particularly preferred embodiment (3-2).
  • the compounds of formula (I) may be according to the invention substituted with the same or with different substituents R. 1
  • the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • the compounds of formula (I) include optionally present E / Z isomers as well as diastereomers or enantiomers.
  • the substituted indole and benzimidazolecarboxamides are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
  • the respective number of substituents n in the formula (I) includes only the substituents which are different from hydrogen. For this reason, hydrogen is not included in the definition of R 1 either. Of course, the substituent is always hydrogen, if no substituent R 1 is present at the respective site.
  • halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.
  • halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine,
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkenyl or alkynyl may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • these substituents may have both an (R) and an (S) configuration.
  • the present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms are independently
  • one chiral center may have the (S) configuration and the other chiral center may have the (S) configuration.
  • the compounds of formula (I) also include optionally present diastereomers or enantiomers as well as E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
  • the invention also relates to the use of the compounds of the general formula (I) according to the invention for the preparation of pesticides. isomers
  • the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions.
  • These stereoisomers are, for example, enantiomers, Diastereomers, atropisomers or geometric isomers.
  • the invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
  • the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
  • the invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
  • pest control always includes the term pesticides.
  • the compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests of the genus Arthropoda in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hi
  • Aulacorthum solani Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp.
  • Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lycorma americanula, Macrosiphum spp., eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosi
  • Pemphigus spp. Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseu
  • Pseudaletia unipuncta Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., eg Schoenobius bipunctifer, Scirpophaga spp., eg Scirpophaga innotata, Ontario segetum, Sesamia spp., eg Sesamia infe Spartoptera spp., Spodoptera spp., Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp.,
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
  • Pests of the Mollusca strain in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
  • Animal and human parasites from the strains of Platyhelminthes and Nematoda e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp.
  • Clonorchis spp. Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp.
  • Hyostrongylus spp. Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria sp Paraglia spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma s
  • Strongyloides spp. Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .;
  • Plant pests from the Nematoda strain ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., eg Criconemella curvata, Criconemella onoensis, Criconemella ornat
  • the compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against Viroids) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
  • B. drench, drip and spray liquors comprising at least one compound of formula (I).
  • the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such as.
  • dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as glycerol and / or fertilizers such as ammonium, potassium or Phosphorus-containing fertilizer.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances.
  • adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • auxiliaries such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as
  • organic solvents as Auxiliary solvents can be used.
  • suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
  • Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g.
  • Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
  • Suitable carriers for granules are: e.g.
  • Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, protein hydrolysates,
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
  • the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
  • the content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
  • the concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie.
  • the application is done in a custom forms adapted to the application. mixtures
  • the compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance.
  • suitable fungicides bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators
  • suitable fungicides bactericides, acaricides, molluscicides, ne
  • the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
  • the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop.
  • the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
  • Suitable mixing partners are, for example, the following compounds:
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos,
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
  • sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, eg acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin , Cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans isomers], deltamethrin, empenthrin [ (EZ) - (lR) -is
  • nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.
  • nAChR nicotinergic acetylcholine receptor
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
  • agents with unknown or non-specific mechanisms of action such as
  • Alkyl halides e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.
  • Selective feeding inhibitors e.g. Pymetrozine or flonicamide.
  • mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • Bacillus thuringiensis subspecies israelensis Bacillus sphaericus
  • Bacillus thuringiensis subspecies aizawai Bacillus thuringiensis subspecies kurstaki
  • Bacillus thuringiensis subspecies tenebrionis and BT plant proteins CrylAb, CrylAc, CrylFa, Cry2Ab, mCry
  • oxidative phosphorylation inhibitors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and Fenbutatin-oxide or Propargite or Tetradifon.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as Bupro fezin.
  • Anti-skinning agents especially in dipterans, i.e., two-toed, such as Cyromazine.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • (21) complex I electron transport inhibitors for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide, other active substances such as Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite,
  • inhibitors of ergosterol biosynthesis such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole , (1.9) Diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidine, ( 1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole cis, (1.21)
  • inhibitors of respiration such as (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, ( 2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empimidal racemate 1RS, 4SR, 9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti- epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS),
  • inhibitors of respiration at the complex III of the respiratory chain, such as (3.1) ametoctradine, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamide, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, ( 3.5) dimoxystrobin, (3.8) enestroburine, (3.9) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxime-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin , (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E) -2
  • resistance inducers such as (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil, and (6.5) laminarin.
  • inhibitors of amino acid and protein biosynthesis such as (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) Pyrimethanil, (7.8) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline and (7.9) oxytetracycline and (7.10) streptomycin.
  • inhibitors of ATP production such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.
  • inhibitors of cell wall synthesis such as (9.1) benthi- avalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamide, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin
  • inhibitors of lipid and membrane synthesis such as (10.1) biphenyl, (10.2) chloroben, (10.3) diclorane, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) Iprobenfos, ( 10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb , (10.12) pyrazophos, (10.13) quintoene, (10.14) tecnazene and (10.15) tolclofos-methyl.
  • inhibitors of melanin biosynthesis such as (11.1) carpropamide, (11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilone, (11.6) tricyclazole, and (11.7) 2,2,2 Trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
  • inhibitors of nucleic acid synthesis such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl,
  • Signal transduction inhibitors such as (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozoline, and (13.8) proquinazide.
  • decouplers such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, and (14.5) meptyldinocap.
  • the compounds of formula (I) may be combined with biological pesticides.
  • Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
  • Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
  • Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
  • NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp.
  • fungi and yeasts which can be used as biological pesticides are:
  • Beauveria bassiana especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
  • Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).
  • viruses that can be used or used as biological pesticides are:
  • Adoxophyes orana Apple peel winder
  • Granulosis virus GV
  • Cydia pomonella codling moth
  • Granulosis virus GV
  • Helicoverpa armigera cotton bollworm
  • Nuclear polyhedrosis virus NPV
  • Spodoptera exigua mNPV
  • Spodoptera frugiperda armyworm
  • mNPV Spodoptera littoralis
  • bacteria and fungi that are added as 'inoculant' plants or plant parts or plant organs and require by their special properties, the plant growth and plant health.
  • examples are: Agrobacterium spp., Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., Especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp.
  • Laccaria spp. Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolu, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
  • plant extracts and such products. which are formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
  • the compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ( ⁇ 4 - [(methylcarbamoyl) amino] phenyl ⁇ sulfonyl) benzamide (CAS 129531- 12-0), 4- (dichloroacetyl) -l-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant
  • Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
  • plants and their parts can be treated according to the invention.
  • wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.Propeas of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention Traits grown by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
  • transgenic Plant, Seed Treatment and Integration Events are any plants that have obtained genetic material through genetic engineering which confer particular beneficial properties ("traits") on these plants.
  • beneficial properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased resistance of the plants to animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes e.g.
  • toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants, furthermore an increased ability to repel the plants against phytopathogenic fungi, bacteria and / or viruses, eg systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as increased tolerance of the plants to certain herbicidal agents, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g., "PAT" gene).
  • SAR systemically acquired resistance
  • systemin phytoalexins
  • elicitors elicitors
  • transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
  • the treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, (spraying) spraying (spraying), sprinkling, evaporation .
  • a preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest.
  • the compounds of the formula (I) also enter the plants via the root system.
  • the treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i.
  • the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
  • Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also incorporate the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.
  • the present invention therefore also relates, in particular, to a method of protecting seed and germinating plants from attack by pests, by mixing the seed with one of the seeds Compounds of formula (I) is treated.
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
  • the invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I).
  • the invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner.
  • the individual substances may be contained in different layers on the seed.
  • the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
  • Compounds of the formula (I) may also be used in combination with signal technology agents, whereby a better colonization with symbionts, such as rhizobia, Mycorrhiza and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation.
  • symbionts such as rhizobia, Mycorrhiza and / or endophytic bacteria or fungi
  • the compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soya, cotton, canola, oilseed rape and rice are examples of seeds of cereals (eg wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with a compound of the formula (I) is also of particular importance.
  • the heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the compound of the formula (I) is applied to the seed.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
  • seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
  • the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates.
  • the compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
  • the compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
  • formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed-dressing formulations of the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
  • the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
  • the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed.
  • the application rates at the connection of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites.
  • animal parasites in particular ectoparasites or endoparasites.
  • endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of formula (I) which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
  • the compounds of formula (I) are administered to mammals.
  • the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
  • control means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, “combating” in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication.
  • the arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp.,
  • arthropods include:
  • Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp
  • Parasitic protozoa include:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica such as Trichomonadidae, for example Giardia lamblia, G.
  • Trypanosomatidae for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L.
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
  • Apicomplexa such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E.
  • Eimeridae for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E.
  • gallopavonis E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. sitesdai E. suis, E. tenella, E.
  • S. suihominis such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
  • Pathogenic endoparasites which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include: Monogenea: e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
  • Cestodes from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp.
  • Taenia spp. Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
  • Trematodes from the genus Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle s
  • Roundworms Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp.
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia s
  • Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
  • Pentastoma from the order Porocephalida for example Linguatula spp ..
  • the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
  • Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent.
  • Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
  • a further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide.
  • Another aspect relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or acaricide
  • an arthropodicide such as an insecticide or acaricide
  • a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
  • pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
  • the pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes).
  • Examples of vectors and their transmitted diseases or pathogens are:
  • Anopheles malaria, filariasis
  • - Aedes yellow fever, dengue fever, filariasis, other viral diseases
  • - Simulia transmission of worms, in particular Onchocerca volvulus
  • flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases; 5) mites: acariosis, typhus, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean Congo fever, Lyme disease;
  • Ticks Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis).
  • vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
  • Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
  • vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
  • Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors.
  • another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
  • the compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
  • the compounds of the formula (I) are present as ready-to-use pesticides, ie, they can be applied to the corresponding material without further changes.
  • insecticides or as fungicides in particular the above-mentioned in question.
  • the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
  • the compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients.
  • they are used in household insecticide products.
  • the compounds of formula (I) are active against sensitive and resistant species and against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • Application is for example in aerosols, non-pressurized sprays, e.g.
  • condensation reagent e.g. [Benztriazole-l-oxyloxy (dimethylamino) methylene] - dimethyl ammonium hexafluorophosphate.
  • Indolecarboxylic acids of the formulas (IIa) are known in some cases (cf., for example, WO-A-2012/119984). Analogously to the process described in WO-A-2012/119984, it is also possible to obtain novel compounds of the formula (IIa) according to Scheme 1. Where L 4 is hydrogen.
  • Benzimidazole carboxylic acids of formula (IIb) are novel and may be e.g. are obtained according to Scheme 2.
  • Benzimidazole derivatives of the formula (IIb) are prepared from compounds of the formula (A-II) by hydrolysis, e.g. obtained with NaOH.
  • Compounds of formula (A-1 L) may be prepared from compounds of formula (A-10b) by reaction in the presence of acidic catalysts, e.g. 4-Toluolsulfonklarehydrat, hydrochloric acid or acetic acid are obtained. The reaction is carried out under conditions known in the literature for analogous compounds (see, e.g., EP1602648, Example 4, Journal of Medicinal Chemistry, 55 (2012) 9089-9106).
  • Compounds of the formula (A-10b) can be obtained together with compounds of the formula (A-10a) by first reacting compounds of the formula (A-8) with thionyl chloride and then the uninsulated intermediate with 1, 2-diaminophenyl derivatives of the formula (A-9). The reaction is carried out under the conditions known in the literature for analogous compounds (see, for example, EP 1602648, Example 4: Journal of Medicinal Chemistry, 55 (2012) 9089-9106).
  • 1,2-Diaminophenyl derivatives of formula (A-9) are known (see for example WO2012 / 119984).
  • Carboxylic acids of the formula (A-8) can be obtained by hydrolysis of esters of the formula (A-7).
  • Carboxylic acids of the formula (A-8) can be prepared analogously to processes known from the literature by ester cleavage from compounds of the general structure (A-7) (for example by NaOH or LiOH.) See Tetrahedron 49 (1993) 3691-3748 for further methods ).
  • Haloalkyl-substituted amines of the general formula (A-4) are commercially available, known from the literature or can be synthesized by methods known from the literature (cf., for example, WO2012 / 119984).
  • 1-aminocyclopropanecarbothioamide of the formula (VII) (CAS No. 1159877-97-0, WO2009 / 070485) is commercially available.
  • Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents. As examples are :.
  • Halogenated hydrocarbons eg chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (eg.
  • chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane,
  • Octylcaprolactam 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, ⁇ , ⁇ '-diformyl-piperazine) and ketones (e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).
  • ketones e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally at absolute pressures between 0.1 and 15 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature.
  • a protective gas atmosphere e.g., under nitrogen, argon or helium
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • amidine bases or guanidine bases eg 7-methyl-1,5,7-triaza- bicyclo (4.4.0) dec-5-ene (MTBD), diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1,8-diazabicyclo (5.4.0) undecene (DBU ), Cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-l, 8-naphthalenediamine,
  • alkaline earth or alkali metal compounds eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium
  • Pentamethylpiperidine and amines, especially tertiary amines, (eg triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, ⁇ , ⁇ -dimethyl-toluidine, N, N-dimethyl-p-aminopyridine , N-methyl-pyrrolidine, N-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline , ⁇ -picoline, ⁇ -picoline, pyrimidine, acridine, ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylenediamine, ⁇ ,
  • mineral acids eg hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid
  • Lewis acids eg aluminum (III) chloride, boron trifluoride or etherate
  • Titanium (IV) chloride, tin (IV) chloride eg formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid
  • the following examples of preparation and use illustrate the invention without limiting it.
  • 6-Chloro-1-ethyl-2 - ( ⁇ 2,2,2-trifluoro-1- [3,5-dichloro-2,4-difluorophenyl] ethyl ⁇ carbamoyl) -H-indole-5-carboxylic acid (prepared according to the method according to WO-A-2012/119984, see page 64, line 16 - page 65, line 1 and page 66, lines 8-11) (0.523 g, 0.98 mmol) was dissolved in DMF (9 mL) , Successively, 1-aminocyclopropanecarbothioamide (0.150 mg, 0.98 mmol), [benztriazol-1-yloxy (dimethylamino) methylene] -dimethyl ammonium hexafluorophosphate (0.374 g, 0.98 mmol) and N-methylmorpholine (0.200 g, 1 , 97 mmol) was added and the reaction mixture then stirred for 15 hours at room temperature.
  • Step 1 Ethyl oxo ( ⁇ 2,2,2-trifluoro-1-f4-fluoro-3- (trifluoromethyl) phenylethyl ⁇ amino) acetate
  • a mixture of 2,2,2-trifluoro-1- (4-fluoro) 3- (trifluoromethyl) phenyl] ethanamine (15.0 g, 57.4 mmol) and 4-methylmorpholine (7.58 mL, 68.9 mmol) in trichloromethane (200 mL) was cooled to 0 ° C, a solution of Ethyl oxalate chloride (8.23 g, 60.3 mmol) in chloroform (100 mL) was slowly added dropwise and then stirred with warming to room temperature for 15 hours.
  • Step 2 Oxo ( ⁇ 2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl ⁇ amino) acetic acid ethyl-oxo ( ⁇ 2,2,2-trifluoro-l- [4 fluoro-3- (trifluoromethyl) phenyl] ethyl ⁇ amino) acetate (20.42 g, 56.0 mmol) were initially charged in a mixture of methanol (200 mL) and water (26 mL) and sodium hydroxide added with stirring ( 8.97 g, 224 mmol). The reaction mixture was stirred for 15 hours at room temperature and then distilled off most of the solvent in vacuo.
  • Ethyl 2-chloro-4- (ethylamino) -5-nitrobenzoate Ethyl 2-chloro-4-fluoro-5-nitrobenzoate (3.60 g, 14.5 mmol) was initially charged in THF (28 mL) and washed with a 2M ethylamine solution in THF (14.5 mL, 29 mmol). Then we stirred for 15 hours at room temperature. For workup, the reaction mixture is added to water and extracted twice with ethyl acetate. The combined organic phases are washed with water and with 5% sodium hydrogen phosphate solution, dried over sodium sulfate and the solvent is distilled off under reduced pressure.
  • Ethyl 5-amino-2-chloro-4- (ethylamino) benzoate ethyl 2-chloro-4- (ethylamino) -5-nitrobenzoate (2.47 g, 9.05 mmol) was dissolved in ethanol (86 mL). / Water (14 mL) and treated with ammonium chloride (775.2 mg, 14.4 mmol). The reaction mixture was heated to 60 ° C, iron powder (5.06 g, 90.5 mmol) was added and then stirred at reflux temperature for 3 hours. After cooling, it was filtered through kieselguhr, washed several times with ethanol, and the solvent was distilled off under reduced pressure.
  • Oxo ( ⁇ 2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl ⁇ amino) acetic acid (2.30 g, 6.90 mmol) was dissolved in trichloromethane (50 mL), with thionyl chloride (2.05 g, 17.2 mmol) and 2 drops of DMF and stirred at 50 ° C for 15 hours.
  • Step 5 6-Chloro-1-ethyl-2 - ( ⁇ 2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) -phenyl-ethyl ⁇ -carbamoyl) -lH-benzimidazole-5-carboxylic acid ethyl-6 -chloro-1-ethyl-2- ( ⁇ 2,2,2-trifluoro-1 - [4-fluoro-3- (trifluoromethyl) phenyl] ethyl ⁇ carbamoyl) -1 H -benzimidazole-5-carboxylate (0.495 g, 0.81 mmol) was initially charged in dioxane (25 mL) / water (2.8 mL) and lithium hydroxide (58.3 mg, 2.43 mmol) was added.
  • Step 6 'N5- (l-Carbamothioylcyclopropyl) -6-chloro-l-ethyl-N2- ⁇ 2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl ⁇ -lH- benzimidazole-2,5-dicarboxamide (Compound No. 1-30)
  • Example I-04 1 H NMR (400.0 MHz, d 6 -DMSO):
  • NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists. NMR peak list procedures
  • the 1 H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; ⁇ ; (intensity ⁇ ;; ⁇ ⁇ (intensity n )
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • tetramethylsilane and / or the chemical shift of the solvent is used, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to.
  • the lists of the 'H NMR peaks are similar to the classical' H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.
  • 'H-NMR prints solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities.
  • our lists of 'H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D6 and the peak of water, which are usually in the Average high intensity.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints.”
  • An expert calculating the peaks of the target compounds by known methods can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 'H NMR interpretation.
  • Tick nymphs (Amblyomma hebraeum) are placed in perforated plastic cups and dipped for one minute at the desired concentration. The ticks are transferred to filter paper in a Petri dish and stored in a climate cabinet.
  • Boophilus microplus injection test (BOOPMI Inj)
  • ⁇ ⁇ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
  • the active ingredient 10 mg are dissolved in 0.5 ml of dimethyl sulfoxide.
  • the active compound solution is diluted with water to the particular desired concentration.
  • This preparation of active compound is pipetted into tubes. 8-10 sucked, adult, female cattle ticks (Boophilus microplus) are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored in an air conditioned room.
  • the effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile. In this test, e.g. the following compounds of the preparation examples have an effect of 100% at an application rate of 20 ppm: 1-30.
  • CTECFE Ctenocephalides felis - Oral test
  • active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
  • Lucilla cuprina - test (LUCICU)
  • active compound 10 mg are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately Twenty LI larvae of the Australian Goldfish fly (Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means> that all larvae have been killed; 0% means that no larvae have been killed.
  • the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 ppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08, 1-09, 1- 10, 1-12, 1-13, 1-16, 1-18, 1-19, 1-20, 1-22, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31, 1-32.
  • Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
  • the kill is determined in%. 100% means> that all flies have been killed; 0% means that none of the flies have been killed.
  • the following compounds of the preparation examples show an effect of 100% at a rate of 100 ppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-09, 1 -10, 1-12, 1-13, 1-16, 1-18, 1-19, 1-20, 1-22, 1-26, 1-27, 1-29, 1-30, 1-31 ,
  • Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0%> means that the number of bile on the treated plants corresponds to the untreated control.
  • Myzus persicae - Spray Test Solvent 78 parts by weight of acetone
  • Emulsifier alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid ⁇ Myzus persicae) are sprayed with an active compound preparation of the desired concentration. After 6 days, the effect is determined in%. 100% means> that all aphids have been killed; 0% means that no aphids have been killed.
  • Phaedon cochleariae - spray test PHAECO
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the effect is determined in%. 100% means> that all beetle larvae have been killed; 0%> means that no beetle larvae have been killed. In this test, z.
  • the following compounds of Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1-08 , 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1 -22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32.
  • SPODFR Spodoptera frugiperda - spray test
  • active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
  • z For example, the following compounds of Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1-08 , 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1 -21, 1-22, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32.
  • the following compounds of the preparation examples effect of 83% at a rate of 100g / ha: 1-23.
  • active compound preparation 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • emulsifier concentration 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • the effect is determined in%. 100%> means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z.
  • the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-02, 1-04, 1-06, 1-07, 1-08, 1-09, 1- 10, 1-11, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-30, 1-31, 1-32.
  • SPODFR Spodoptera frugiperda - spray test
  • Emulsifier alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperda).
  • the effect is determined in%. 100% means> that all caterpillars have been killed; 0% means that no caterpillar has been killed.
  • Emulsifier alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution.
  • Bush bean plants Phaseolus vulgaris
  • the treated plants are infected with a mixed thrip population (Frankliniella occidentalis).
  • the phytosanitary effect is determined in%. 100% means that no damage can be seen; 0% means that the damage to the treated plant matches that of the untreated control.
  • Diabrotica balteata - Drench test (DIABBA) Solvent 7 parts by weight of dimethylformamide
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, whereby the volume of the earth is forced into the vessel. It must be ensured that a concentration of 40 ppm emulsifier is not exceeded in the soil. To prepare further test concentrations, it is diluted with water.
  • corn kernels are seeded in pots filled with soil (Zea mays) and poured on the following day with the preparation of active compound of the desired concentration. After one day, 25 L2 larvae of the corn rootworm ⁇ Diabrotica balteata) are added.
  • Emulsifier alkylaryl polyglycol ether
  • 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration.
  • dilute with emulsifier-containing water Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

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Abstract

The present invention relates to compounds of general formula (I), in which R1 to R6, G and n have the meanings given in the description, and to a process for the production thereof and the use thereof as insecticides and acaricides.

Description

Indol- und Benzimidazolcarbonsäureamide als Insektizide und Akarizide  Indole and benzimidazolecarboxamides as insecticides and acaricides
Die vorliegende Erfindung betrifft neue Schädlingsbekämpfungsmittel, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Wirkstoffe, insbesondere ihre Verwendung als Insektizide und Akarizide. The present invention relates to novel pesticides, a process for their preparation and their use as active ingredients, in particular their use as insecticides and acaricides.
In der Literatur sind Indol-2-carboxamide und Benzimidazol-2-carboxamide und ihre Verwendung als Arzneimittel beschrieben, siehe beispielsweise WO-A-2010/126164, WO-A-2010/054138, US 2009/0041722, WO-A-2007/115938, EP1460064, WO-A-2004-A-056768, WO-A-2004/032921, WO- A-20010/32622. WO-A-2012/119984 offenbart Indol-2-carboxamide und Benzimidazol-2-carboxamide und ihre Verwendung als Pflanzenschutzmittel. Dort ist in Beispiel 273 eine Verbindung offenbart, die eine Aminothiocarbonylcyclopropyl-Substitution des Amid-Restes am Indol-Sechsring aufweist. Allerdings ist diese Verbindung am Phenylring nur einfach mit Trifluormethyl substituiert. The literature describes indole-2-carboxamides and benzimidazole-2-carboxamides and their use as drugs, see, for example, WO-A-2010/126164, WO-A-2010/054138, US 2009/0041722, WO-A-2007 / 115938, EP1460064, WO-A-2004-A-056768, WO-A-2004/032921, WO-A-20010/32622. WO-A-2012/119984 discloses indole-2-carboxamides and benzimidazole-2-carboxamides and their use as crop protection agents. There, in Example 273, a compound is disclosed which has an aminothiocarbonylcyclopropyl substitution of the amide residue on the indole six-membered ring. However, this compound is only substituted on the phenyl ring with trifluoromethyl.
Es wurde nun überraschend gefunden, dass bestimmte neue Indol- und Benzimidazolcarbonsäureamide starke Insektizide und akarizide Eigenschaften bei gleichzeitig guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit besitzen. Die erfindungsgemäßen neuen Verbindungen wurden bislang nicht offenbart. Moderne Pflanzenschutzmittel müssen vielen Anforderungen genügen, beispielsweise in Bezug auf Höhe, Dauer und Breite ihrer Wirkung und möglichen Verwendung. Es spielen Fragen der Toxizität, der Kombinierbarkeit mit anderen Wirkstoffen oder Formulierhilfsmitteln eine Rolle sowie die Frage des Aufwands, der für die Synthese eines Wirkstoffs betrieben werden muss. Ferner können Resistenzen auftreten. Aus all diesen Gründen kann die Suche nach neuen Pflanzenschutzmitteln nie als abgeschlossen betrachtet werden und es besteht ständig Bedarf an neuen Verbindungen mit gegenüber den bekannten Verbindungen zumindest in Bezug auf einzelne Aspekte verbesserten Eigenschaften. It has now surprisingly been found that certain new indole and benzimidazolecarboxamides have strong insecticidal and acaricidal properties with at the same time good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility. The novel compounds of the invention have not been disclosed. Modern plant protection products have to meet many requirements, for example with regard to the amount, duration and breadth of their effect and possible use. Issues of toxicity, of the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can never be considered complete and there is a constant need for new compounds with improved properties over the known compounds, at least with respect to individual aspects.
Aufgabe der vorliegenden Erfindung war es, Verbindungen bereitzustellen, durch die das Spektrum der Schädlingsbekämpfungsmittel unter verschiedenen Aspekten verbreitert und/oder ihre Aktivität verbessert wird. Die neuen Verbindungen der Formel (I) zeichnen sich insbesondere dadurch aus, dass sie eine Aminothiocarbonylcyclopropyl-Substitution des Amid-Restes am Indol-Sechsring aufweisen und dass der Phenylring mehrfach substituiert ist, wobei mindestens einer dieser Substituenten Halogen ist. Die Kombination dieser Merkmale führt überraschend zu einer verbesserten biologischen Wirksamkeit. Das ergibt sich aus den gezeigten biologischen Anwendungsbeispielen. Gegenstand der vorliegenden Erfindung sind daher Verbindungen der allgemeinen Formel (I) The object of the present invention was to provide compounds which broaden the spectrum of pesticides in various aspects and / or improve their activity. The novel compounds of the formula (I) are notable in particular in that they have an aminothiocarbonylcyclopropyl substitution of the amide radical on the indole six-membered ring and that the phenyl ring is polysubstituted, where at least one of these substituents is halogen. The combination of these features surprisingly leads to improved biological effectiveness. This results from the biological application examples shown. The present invention therefore relates to compounds of the general formula (I)
wobei in which
R1 für Cyano, Fluor, Chlor, Brom, lod, Difluormethyl, Dichlorfluormethyl, Chlordifluormethyl, Trifluormethyl, Pentafluorethyl, Chlortetrafluorethyl, Difluormethoxy, Trifluormethoxy steht, wobei mindestens ein Substituent R1 für Fluor, Chlor, Brom oder lod steht, R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, chlorotetrafluoroethyl, difluoromethoxy, trifluoromethoxy, at least one substituent R 1 being fluorine, chlorine, bromine or iodine,
R2 für Fluor, Trifluormethyl oder Wasserstoff steht. n für 2, 3, 4 oder 5 steht R 2 is fluorine, trifluoromethyl or hydrogen. n stands for 2, 3, 4 or 5
R3 für Wasserstoff steht, R4 für Wasserstoff, Methyl, Ethyl, Prop-l-yl, Prop-2-en-l-yl, Prop-2-in-l-yl, Ethenyl, But-2-in-l-yl steht, R 3 is hydrogen, R 4 is hydrogen, methyl, ethyl, prop-1-yl, prop-2-en-1-yl, prop-2-yn-1-yl, ethenyl, but-2-yn-1 -yl stands,
G für CH oder N steht, G is CH or N,
R6 für Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl oder Trifluormethyl steht, sowie Salze und N-Oxide von Verbindungen der Formel (I) und deren Anwendung zur Bekämpfung von tierischen Schädlingen. R 6 represents cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl or trifluoromethyl, and salts and N-oxides of compounds of the formula (I) and their use for controlling animal pests.
In einer bevorzugten Ausführungsform (2-1) der Erfindung stehen In a preferred embodiment (2-1) of the invention
R1 für Fluor, Chlor, Brom, lod oder Trifluormethyl, wobei mindestens ein Substituent R1 für Fluor, Chlor, Brom oder lod steht, R 1 is fluorine, chlorine, bromine, iodine or trifluoromethyl, where at least one substituent R 1 is fluorine, chlorine, bromine or iodine,
R2 für Fluor oder Wasserstoff n für 2, 3 oder 4, R3 für Wasserstoff, R 2 is fluorine or hydrogen is n 2, 3 or 4, R 3 is hydrogen,
R4 für Wasserstoff, Methyl, Ethyl oder Prop-2-in-l -yl, G für CH oder N, R 4 is hydrogen, methyl, ethyl or prop-2-yn-1-yl, G is CH or N,
R6 für Chlor, Brom, Methyl oder Trifluormethyl, sowie Salze und N-Oxide von Verbindungen der Formel (I) und deren Anwendung zur Bekämpfung von tierischen Schädlingen. R 6 represents chlorine, bromine, methyl or trifluoromethyl, and salts and N-oxides of compounds of the formula (I) and their use for controlling animal pests.
In einer besonders bevorzugten Ausführungsform (3-1) steht R1 für Fluor, Chlor, Brom oder Trifluormethyl und n für 2, 3 oder 4, wobei mindestens ein Substituent R1 für Fluor oder Chlor steht, und alle anderen Gruppen, Reste und Substituenten die oben für die bevorzugte Ausführungsform (2-1) genannte Bedeutung haben. In a particularly preferred embodiment (3-1) R 1 is fluorine, chlorine, bromine or trifluoromethyl and n is 2, 3 or 4, wherein at least one substituent R 1 is fluorine or chlorine, and all other groups, radicals and substituents have the meaning given above for the preferred embodiment (2-1).
In einer weiteren besonders bevorzugten Ausführungsform (3-2) steht R6 für Chlor oder Methyl, wobei alle anderen Gruppen, Reste und Substituenten die oben für die bevorzugte Ausführungsform (2-1) oder die oben für die besonders bevorzugte Ausführungsform (3-1) genannte Bedeutung haben. In a further particularly preferred embodiment (3-2), R 6 is chlorine or methyl, all other groups, radicals and substituents being those described above for the preferred embodiment (2-1) or the above for the particularly preferred embodiment (3-1 ).
In einer weiteren besonders bevorzugten Ausführungsform (3-3) steht G für CH, wobei alle anderen Gruppen, Reste und Substituenten die oben für die bevorzugte Ausführungsform (2-1) oder die oben für die besonders bevorzugte Ausführungsform (3-1) oder die oben für die besonders bevorzugte Ausführungsform (3-2) genannte Bedeutung haben. In another particularly preferred embodiment (3-3), G is CH, with all other groups, radicals and substituents as described above for the preferred embodiment (2-1) or the above for the particularly preferred embodiment (3-1) or the have the meaning given above for the particularly preferred embodiment (3-2).
In einer weiteren besonders bevorzugten Ausführungsform (3-4) steht G für N, wobei alle anderen Gruppen, Reste und Substituenten die oben für die bevorzugte Ausführungsform (2-1) oder die oben für die besonders bevorzugte Ausführungsform (3-1) oder die oben für die besonders bevorzugte Ausführungsform (3-2) genannte Bedeutung haben. In a further particularly preferred embodiment (3-4) G is N, where all other groups, radicals and substituents are those described above for the preferred embodiment (2-1) or the above for the particularly preferred embodiment (3-1) or the have the meaning given above for the particularly preferred embodiment (3-2).
Die Verbindungen der Formel (I) können erfindungsgemäß mit den gleichen oder mit verschiedenen Substituenten R1 substituiert sein. The compounds of formula (I) may be according to the invention substituted with the same or with different substituents R. 1
Die Verbindungen der Formel (I) können gegebenenfalls in verschiedenen polymorphen Formen oder als Mischung verschiedener polymorpher Formen vorliegen. Sowohl die reinen Polymorphe als auch die Polymorphgemische sind Gegenstand der Erfindung und können erfindungsgemäß verwendet werden. The compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
Die Verbindungen der Formel (I) umfassen gegebenenfalls vorliegende E/Z-Isomere sowie Diastereomere oder Enantiomere. Die substituierten Indol- und Benzimidazolcarbonsäureamide sind durch die Formel (I) allgemein definiert. Bevorzugte Restedefinitionen der vorstehenden und nachfolgend genannten Formeln sind im Folgenden angegeben. Diese Definitionen gelten für die Endprodukte der Formel (I) wie für alle Zwischenprodukte gleichermaßen. Die jeweilige Zahl der Substituenten n in der Formel (I) umfasst dabei nur die Substituenten, die von Wasserstoff verschieden sind. Aus diesem Grund ist Wasserstoff in der Definition von R1 auch nicht enthalten. Natürlich steht als Substituent immer Wasserstoff, wenn kein Substituent R1 an der jeweiligen Stelle vorhanden ist. The compounds of formula (I) include optionally present E / Z isomers as well as diastereomers or enantiomers. The substituted indole and benzimidazolecarboxamides are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates. The respective number of substituents n in the formula (I) includes only the substituents which are different from hydrogen. For this reason, hydrogen is not included in the definition of R 1 either. Of course, the substituent is always hydrogen, if no substituent R 1 is present at the respective site.
In den bevorzugten Definitionen ist, sofern nichts anderes angegeben ist, Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom. In the preferred definitions, unless otherwise stated, halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine.
In den besonders bevorzugten Definitionen ist, sofern nichts anderes angegeben ist, Halogen ausgewählt aus der Reihe Fluor, Chlor, Brom und Iod, bevorzugt wiederum aus der Reihe Fluor, Chlor und Brom, In the particularly preferred definitions, unless otherwise stated, halogen is selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine,
Durch Halogen substituierte Reste, z.B. Haloalkyl (= Halogenalkyl), sind einfach oder mehrfach bis zur maximal möglichen Substituentenzahl halogeniert. Bei mehrfacher Halogenierung können die Halogenatome gleich oder verschieden sein. Halogen steht dabei für Fluor, Chlor, Brom oder Iod, insbesondere für Fluor, Chlor oder Brom. Halogen substituted radicals, e.g. Haloalkyl (= haloalkyl) are halogenated once or several times up to the maximum possible number of substituents. For multiple halogenation, the halogen atoms may be the same or different. Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
Gesättigte oder ungesättigte Kohlenwasserstoffreste wie Alkyl, Alkenyl oder Alkinyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein. Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können. Saturated or unsaturated hydrocarbon radicals such as alkyl, alkenyl or alkynyl may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched. Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangsprodukte und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden. The general or preferred radical definitions or explanations given above apply correspondingly to the end products and to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges.
Erfindungsgemäß bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegt. Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
Erfindungsgemäß besonders bevorzugt werden Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. Ebenfalls bevorzugte erfindungsgemäße Verbindungen sind die in Tabelle 1 gezeigten Verbindungen der allgemeinen Formel (I). Die vorliegenden Verbindungen der allgemeinen Formel (I) können gegebenenfalls ein chirales Kohlenstoffatom aufweisen. Particular preference according to the invention is given to compounds of the formula (I) in which a combination of the meanings listed above as being particularly preferred is present. Likewise preferred compounds according to the invention are the compounds of general formula (I) shown in Table 1. The present compounds of the general formula (I) may optionally have a chiral carbon atom.
Gemäß den Regeln nach Cahn, Ingold und Prelog (CIP-Regeln) können diese Substituenten sowohl eine (R)- als auch eine (S)-Konfiguration aufweisen. Von der vorliegenden Erfindung werden Verbindungen der allgemeinen Formel (I) sowohl mit (S)- als auch mit (R)-Konfiguration an den jeweiligen chiralen Kohlenstoffatomen umfasst, d.h., dass die vorliegende Erfindung die Verbindungen der allgemeinen Formel (I) erfasst, in welchen die betreffenden Kohlenstoffatome jeweils unabhängig voneinander According to the rules of Cahn, Ingold and Prelog (CIP rules), these substituents may have both an (R) and an (S) configuration. The present invention encompasses compounds of the general formula (I) having both (S) and (R) configuration at the respective chiral carbon atoms, that is, that the present invention covers the compounds of the general formula (I), in each of which carbon atoms are independently
(1) eine (R)-Konfiguration; oder (2) eine (S)-Konfiguration aufweisen. Wenn mehrere Chiralitätszentren in den Verbindungen der allgemeinen Formel (I) vorliegen, sind beliebige Kombinationen der Konfigurationen der Chiralitätszentren möglich, d.h. dass (1) an (R) configuration; or (2) have an (S) configuration. When multiple chiral centers are present in the compounds of general formula (I), any combinations of the configurations of the chiral centers are possible, i. that
(1) ein Chiralitätszentrum die (R)-Konfiguration und das andere Chiralitätszentrum die (S)- Konfiguration; (2) ein Chiralitätszentrum die (R)-Konfiguration und das andere Chiralitätszentrum die (R)- Konfiguration; und (1) one chiral center the (R) configuration and the other chiral center the (S) configuration; (2) one chiral center the (R) configuration and the other chiral center the (R) configuration; and
(3) ein Chiralitätszentrum die (S)-Konfiguration und das andere Chiralitätszentrum die (S)- Konfiguration aufweisen kann. Die Verbindungen der Formel (I) umfassen ebenfalls gegebenenfalls vorliegende Diastereomere oder Enantiomere sowie E/Z-Isomere sowie Salze und N-Oxide von Verbindungen der Formel (I) und deren Anwendung zur Bekämpfung von tierischen Schädlingen. (3) one chiral center may have the (S) configuration and the other chiral center may have the (S) configuration. The compounds of formula (I) also include optionally present diastereomers or enantiomers as well as E / Z isomers and salts and N-oxides of compounds of formula (I) and their use for controlling animal pests.
Die Erfindung betrifft auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) zur Herstellung von Schädlingsbekämpfungsmitteln. Isomere The invention also relates to the use of the compounds of the general formula (I) according to the invention for the preparation of pesticides. isomers
Die Verbindungen der Formel (I) können in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Diese Stereoisomere sind beispielsweise Enantiomere, Diastereomere, Atropisomere oder geometrische Isomere. Die Erfindung umfasst somit reine Stereoisomere als auch beliebige Gemische dieser Isomere. Depending on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and / or as optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, Diastereomers, atropisomers or geometric isomers. The invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
Verfahren und Verwendungen Methods and uses
Die Erfindung betrifft auch Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der Formel (I) auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt. Bevorzugt wird die Bekämpfung der tierischen Schädlinge in der Land- und Forstwirtschaft und im Materialschutz durchgeführt. Hierunter vorzugsweise ausgeschlossen sind Verfahren zur chirurgischen oder therapeutischen Behandlung des menschlichen oder tierischen Körpers und Diagnostizierverfahren, die am menschlichen oder tierischen Körper vorgenommen werden. Die Erfindung betrifft ferner die Verwendung der Verbindungen der Formel (I) als Schädlingsbekämpfungsmittel, insbesondere Pflanzenschutzmittel. The invention also relates to methods for controlling animal pests, in which compounds of the formula (I) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body. The invention further relates to the use of the compounds of the formula (I) as pesticides, in particular pesticides.
Im Rahmen der vorliegenden Anmeldung umfasst der Begriff Schädlingsbekämpfungsmittel immer auch den Begriff Pflanzenschutzmittel. In the context of the present application, the term pest control always includes the term pesticides.
Die Verbindungen der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen vor biotischen und abiotischen Stressfaktoren, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren, Helminthen, Nematoden und Mollusken, die in der Landwirtschaft, im Gartenbau, bei der Tierzucht, in Aquakulturen, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Schädlingsbekämpfungsmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören: The compounds of the formula (I) are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs from biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, Arachnids, helminths, nematodes and molluscs found in agriculture, horticulture, livestock, aquaculture, forestry, gardens and recreation, storage and materials protection and hygiene. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Schädlinge aus dem Stamm der Arthropoda, insbesondere aus der Klasse der Arachnida z.B. Acarus spp., z.B. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., z.B. Aculus fockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., z.B. Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., z.B. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp., z.B. Eutetranychus banksi, Eriophyes spp., z.B. Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., z.B. Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., z.B. Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., z.B. Panonychus citri (=Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., z.B. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., z.B. Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; aus der Klasse der Chilopoda z.B. Geophilus spp., Scutigera spp.; aus der Ordnung oder der Klasse der Collembola z.B. Onychiurus armatus; Sminthurus viridis; aus der Klasse der Diplopoda z.B. Blaniulus guttulatus; aus der Klasse der Insecta, z.B. aus der Ordnung der Blattodea z.B. Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., z.B. Periplaneta americana, Periplaneta australasiae, Supella longipalpa; aus der Ordnung der Coleoptera z.B. Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., z.B. Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., z.B. Anthonomus grandis, Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., z.B. Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., z.B. Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., z.B. Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., z.B. Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., z.B. Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., z.B. Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., z.B. Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., z.B. Epilachna borealis, Epilachna varivestis, Epitrix spp., z.B. Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.B. Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., z.B. Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., z.B. Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., z.B. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., z.B. Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., z.B. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., z.B. Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., z.B. Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Sternechus spp., z.B. Sternechus paludatus, Symphyletes spp., Tanymecus spp., z.B. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., z.B. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., z.B. Zabrus tenebrioides; aus der Ordnung der Diptera z.B. Aedes spp., z.B. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., z.B. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., z.B. Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., z.B. Bactrocera Cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., z.B. Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia tritici,Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., z.B. Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., z.B. Dasineura brassicae, Delia spp., z.B. Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., z.B. Drosphila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., z.B. Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., z.B. Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., z.B. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya spp., z.B. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., z.B. Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., z.B. Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., z.B. Tipula paludosa, Tipula simplex; aus der Ordnung der Hemiptera z.B. Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., z.B. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., z.B. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., z.B. Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., z.B. Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., z.B. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., z.B. Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., z.B. Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., z.B. Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., z.B. Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca stevensi, Eriosoma spp., z.B. Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., z.B. Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., z.B. Lecanium corni (=Parthenolecanium corni), Lepidosaphes spp., z.B. Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., z.B. Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., z.B. Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., z.B. Nephotettix cinetieeps,, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., z.B. Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., z.B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., z.B. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., z.B. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., z.B. Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., z.B. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., z.B. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., z.B. Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., z.B. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetia spp., z.B. Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis,Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., z.B. Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., z.B. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; aus der Unterordnung der Heteroptera z.B. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., z.B. Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., z.B. Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., z.B. Lygocoris pabulinus, Lygus spp., z.B. Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Monaionion atratum, Nezara spp., z.B. Nezara viridula, Oebalus spp., Piesma quadrata, Piezodorus spp., z.B. Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; aus der Ordnung der Hymenoptera z.B. Acromyrmex spp., Athalia spp., z.B. Athalia rosae, Atta spp., Diprion spp., z.B. Diprion similis, Hoplocampa spp., z.B. Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Monomorium pharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., z.B. Vespa crabro, Xeris spp.; aus der Ordnung der Isopoda z.B. Armadillidium vulgare, Oniscus asellus, Porcellio scaber; aus der Ordnung der Isoptera z.B. Coptotermes spp., z.B. Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., z.B. Reticulitermes flavipes, Reticulitermes hesperus; aus der Ordnung der Lepidoptera z.B. Achroia grisella, Acronicta major, Adoxophyes spp., z.B. Adoxophyes orana, Aedia leucomelas, Agrotis spp., z.B. Agrotis segetum, Agrotis ipsilon, Alabama spp., z.B. Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., z.B. Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., z.B. Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., z.B. Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., z.B. Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., z.B. Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., z.B. Grapholita molesta, Grapholita prunivora, Hedylepta spp., Helicoverpa spp., z.B. Helicoverpa armigera, Helicoverpa zea, Heliothis spp., z.B. Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Leucinodes orbonalis, Leucoptera spp., z.B. Leucoptera coffeella, Lithocolletis spp., z.B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., z.B. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., z.b. Lymantria dispar, Lyonetia spp., z.B. Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., z.B. Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., z.B. Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., z.B. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., z.B. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., z.B. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (=Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., z.B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., z.B. Schoenobius bipunctifer, Scirpophaga spp., z.B. Scirpophaga innotata, Scotia segetum, Sesamia spp., z.B. Sesamia inferens, Sparganothis spp., Spodoptera spp., z.b. Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., z.B. Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp.; aus der Ordnung der Orthoptera oder Saltatoria z.B. Acheta domesticus, Dichroplus spp., Gryllotalpa spp., z.B. Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., z.B. Locusta migratoria, Melanoplus spp., z.B. Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; aus der Ordnung der Phthiraptera z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp.; aus der Ordnung der Psocoptera z.B. Lepinotus spp., Liposcelis spp.; aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Ctenocephalides spp., z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; aus der Ordnung der Thysanoptera z.B. Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., z.B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., z.B. Thrips palmi, Thrips tabaci; aus der Ordnung der Zygentoma (= Thysanura), z. B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; aus der Klasse der Symphyla z.B. Scutigerella spp., z.B. Scutigerella immaculata; Pests of the genus Arthropoda, in particular of the class Arachnida eg Acarus spp., Eg Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., Eg Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Eg Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Eg Eotetranychus hicoriae , Epitrimerus pyri, Eutetranychus spp., Eg Eutetranychus banksi, Eriophyes spp., Eg Eriophyes pyri, Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Eg Hemitarsonemus latus (= Polyphagotarsonemus latus), Hyalomma spp., Ixodes spp., Latrodectus spp. , Loxosceles spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Eg Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., Eg Panonychus citri (= Metatetranychus citri), Panonychus ulmi (= Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychus multidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., Eg Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., Eg Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani , Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici; from the genus of Chilopoda, for example Geophilus spp., Scutigera spp .; from the order or class of Collembola eg Onychiurus armatus; Sminthurus viridis; from the class Diplopoda eg Blaniulus guttulatus; from the class of the Insecta, eg from the order of the Blattodea eg Blatta orientalis, Blattella asahinai, Blattella germanica, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., eg Periplaneta americana, Periplaneta australasiae, Supella longipalpa; from the order of the Coleoptera eg Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., eg Agriotes linneatus, Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., eg Anthonomus grandis , Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Eg Atomaria linearis, Attagenus spp., Baris caerulescens, Bruchidius obtectus, Bruchus spp., Eg Bruchus pisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata, Ceutorrhynchus eg Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae, Chaetocnema spp., eg Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus, Conoderus spp., Cosmopolites spp., eg Cosmopolites sordidus, Costelytra zealandica, Ctenicera spp., Curculio spp., eg Curculio caryae, Curculio caryatrypeSjCurculio obtusus, Curculio sayi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp., Diabrotica spp., eg Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., Eg Epilachna borealis, Epilachna varivestis, Epitrix spp., Eg Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator , Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Eg Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., eg Leucoptera coffeella, Lissorhoptrus oryzophilus, Lixus spp., Luperomorpha xanthodera, Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., eg Melanotus longulus oregonensis, Meligethes aeneus, Melolontha spp., eg Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, oryzae Oryzaphagus, Otiorhynchus spp., for example, Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., eg Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., eg Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Eg S itophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais, Sphenophorus spp., Stegobium paniceum, Starchus spp., eg Starchus paludatus, Symphyletes spp., Tanymecus spp., eg Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus Tribolium spp., Eg Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., Eg Zabrus tenebrioides; from the order of the Diptera eg Aedes spp., eg Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., eg Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., eg Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp., eg Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp Contarinia johnsoni, Contarina nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarina sorghicola, Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., eg Culex pipiens, Culex quinquefasciatus, Culicoides spp., Culiseta spp., Cuterebra spp. Dacus oleae, Dasineura spp., Eg, Dasineura brassicae, Delia spp., Eg Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila sp p., eg, Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., eg Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Lucilla spp., eg Lucilla cuprina, Lutzomyia spp., Mansonia spp., Musca spp., eg Musca domestica, Musca domestica vicina, Oestrus spp., Oscinella frit, Paratanytarsus spp , Paralauterborniella subcincta, Pegomya spp., Eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora, Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., Eg Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp., Simulium spp., eg Simulium meridionale, Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp., eg Tipula paludosa, Tipula simplex; from the order of the Hemiptera eg Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., eg Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Eg Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp., Eg Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata, Aphanostigma piri, Aphis spp., Eg Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines , Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphis viburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., Eg Aspidiotus nerii, Atanus spp. , Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp. , eg Cacopsylla pyricola, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., eg Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., eg Dysaphis apiifolia, Dysaphis plantaginea , Dysaphis tulipae, Dysmicoccus spp., Empoasca spp., Eg Empoasca abrupta, Empoasca fabae, Empoasca maligna, Empoasca Solana, Empoasca stevensi, Eriosoma spp., Eg Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneura spp., Eucalyptolyma spp. Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., Eg Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Eg Lecanium corni (= Parthenolecanium corni), Lepidosaphes spp., Eg Lepidosaphes ulmi, Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp., eg Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., eg Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae ,. Myzus nicotianae, Nasonovia ribisnigri, Nephotettix spp., Eg Nephotettix cinetieeps, Nephotettix nigropictus, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., Eg Paratrioza cockerelli, Parlatoria spp. Pemphigus spp., Eg Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Phenacoccus spp., Eg Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Eg Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., Eg Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Eg Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., Eg Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp. , Pyrilla spp., Quadraspidiotus spp., Eg Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., eg Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., eg Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sitobion avenae, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., eg Toxoptera aurantii, Toxoptera citricidus, Trialeurodes vaporariorum, Trioza spp., Eg Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the suborder of the Heteroptera eg Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., eg Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., eg Eusystus heros, Euschistus servus, Eustistus tristigmus, Eushtistus variolarius, Eurygaster spp., Halyomorpha halys, Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocoris varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., Eg Lygocoris pabulinus, Lygus spp., Eg Lygus elisus, Lygus hesperus, Lygus lineolaris, Macropes excavatus, Monaionion atratum, Nezara spp., Eg Nezara viridula, Oebalus Spp., Piesma quadrata, Piezodorus spp., eg, Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nas hi, Tibraca spp., Triatoma spp .; from the order of the Hymenoptera eg Acromyrmex spp., Athalia spp., eg Athalia rosae, Atta spp., Diprion spp., eg Diprion similis, Hoplocampa spp., eg Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Monomorium pharaonis, Sirex spp , Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., Eg Vespa crabro, Xeris spp .; from the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Isoptera eg Coptotermes spp., eg Coptotermes formosanus, Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp., eg Reticulitermes flavipes, Reticulitermes hesperus; from the order of the Lepidoptera eg Achroia grisella, Acronica major, Adoxophyes spp., eg Adoxophyes orana, Aedia leucomelas, Agrotis spp., eg Agrotis segetum, Agrotis ipsilon, Alabama spp., eg Alabama argillacea, Amyelois transitella, Anarsia spp., Anticarsia spp., eg Anticarsia gemmatalis, Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus pinarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp. eg, Chilo plejadellus, Chilo suppressalis, Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Eg Cydia nigricana, Cydia pomonella, Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp. eg Ephestia elutella, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., eg Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp Helicoverpa spp., eg Helicoverpa armigera, Helicoverpa zea, Heliothis spp., eg Heliothis virescens Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp , Leucinodes orbonalis, Leucoptera spp., Eg Leucoptera coffeella, Lithocolletis spp., Eg Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Eg Lobesia botrana, Loxagrotis albicosta, Lymantria spp. , eg Lymantria dispar, Lyonetia spp., eg, Lyonetia clerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp. Orthaga spp., Ostrinia spp., Eg Ostrinia nubilalis, Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Eg Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Eg Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp ., eg Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., eg Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella (= Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp. eg Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., eg Schoenobius bipunctifer, Scirpophaga spp., eg Scirpophaga innotata, Scotia segetum, Sesamia spp., eg Sesamia infe Spartoptera spp., Spodoptera spp., Spodoptera frugiperda, Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., eg Trichoplusia ni, Tryporyza incertulas, Tuta absoluta, Virachola spp .; from the order of Orthoptera or Saltatoria eg Acheta domesticus, Dichroplus spp., Gryllotalpa spp., eg Gryllotalpa gryllotalpa, Hieroglyphus spp., Locusta spp., eg Locusta migratoria, Melanoplus spp., eg Melanoplus devastator, Paratlanticus ussuriensis, Schistocerca gregaria; from the order of Phthiraptera eg Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxera vastatrix, Phthirus pubis, Trichodectes spp .; from the order of Psocoptera eg Lepinotus spp., Liposcelis spp .; from the order of Siphonaptera eg Ceratophyllus spp., Ctenocephalides spp., eg Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Thysanoptera eg Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp., eg Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniella williamsi, Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus , Scirtothrips spp., Taeniothrips cardamomi, Thrips spp., Eg Thrips palmi, Thrips tabaci; from the order of Zygentoma (= Thysanura), z. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla eg Scutigerella spp., eg Scutigerella immaculata;
Schädlinge aus dem Stamm der Mollusca, insbesondere aus der Klasse der Bivalvia, z.B. Dreissena spp.; sowie aus der Klasse der Gastropoda z.B. Arion spp., z.B. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., z.B. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; Pests of the Mollusca strain, in particular of the bivalve class, e.g. Dreissena spp .; and from the class of Gastropoda e.g. Arion spp., E.g. Arion ater rufus, Biomphalaria spp., Bulinus spp., Deroceras spp., E.g. Deroceras laeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .;
Tier- und Humanparasiten aus den Stämmen der Platyhelminthes und Nematoda, z.B. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp., Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp., Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria spp., Parafilaria spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp., Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp.; Animal and human parasites from the strains of Platyhelminthes and Nematoda, e.g. Aelurostrongylus spp., Amidostomum spp., Ancylostoma spp, Angiostrongylus spp., Anisakis spp., Anoplocephala spp., Ascaris spp., Ascaridia spp., Baylisascaris spp., Brugia spp., Bunostomum spp., Capillaria spp., Chabertia spp. , Clonorchis spp., Cooperia spp., Crenosoma spp., Cyathostoma spp., Dicrocoelium spp., Dictyocaulus spp., Diphyllobothrium spp., Dipylidium spp., Dirofilaria spp., Dracunculus spp., Echinococcus spp., Echinostoma spp., Enterobius spp., Eucoleus spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Filaroides spp., Gongylonema spp., Gyrodactylus spp., Habronema spp., Haemonchus spp., Heligmosomoides spp., Heterakis spp., Hymenolepis spp. , Hyostrongylus spp., Litomosoides spp., Loa spp., Metastrongylus spp., Metorchis spp., Mesocestoides spp., Moniezia spp., Muellerius spp., Necator spp., Nematodirus spp., Nippostrongylus spp., Oesophagostomum spp., Ollulanus spp., Onchocerca spp, Opisthorchis spp., Oslerus spp., Ostertagia spp., Oxyuris spp., Paracapillaria sp Paraglia spp., Paragonimus spp., Paramphistomum spp., Paranoplocephala spp., Parascaris spp., Passalurus spp., Protostrongylus spp., Schistosoma spp., Setaria spp., Spirocerca spp., Stephanofilaria spp., Stephanurus spp. , Strongyloides spp., Strongylus spp., Syngamus spp., Taenia spp., Teladorsagia spp., Thelazia spp., Toxascaris spp., Toxocara spp., Trichinella spp., Trichobilharzia spp., Trichostrongylus spp., Trichuris spp., Uncinaria spp., Wuchereria spp .;
Pflanzenschädlinge aus dem Stamm der Nematoda, d.h. pflanzenparasitäre Nematoden, insbesondere Aglenchus spp., z.B. Aglenchus agricola, Anguina spp., z.B. Anguina tritici, Aphelenchoides spp., z.B. Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., z.B. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., z.B. Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., z.B. Cacopaurus pestis, Criconemella spp., z.B. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., z.B. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., z.B. Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., z.B. Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., z.B. Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., z.B. Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp., z.B. Longidorus africanus, Meloidogyne spp., z.B. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp., Paratrichodorus spp., z.B. Paratrichodorus minor, Pratylenchus spp., z.B. Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., z.B. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., z.B. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., z.B. Tylenchorhynchus annulatus, Tylenchulus spp., z.B. Tylenchulus semipenetrans, Xiphinema spp., z.B. Xiphinema index. Weiterhin lässt sich aus dem Unterreich der Protozoa die Ordnung der Coccidia z.B. Eimeria spp. bekämpfen. Plant pests from the Nematoda strain, ie plant parasitic nematodes, in particular Aglenchus spp., Eg Aglenchus agricola, Anguina spp., Eg Anguina tritici, Aphelenchoides spp., Eg Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp., Eg Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus spp., Eg Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., Eg Cacopaurus pestis, Criconemella spp., eg Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= Mesocriconema xenoplax), Criconemoides spp., eg Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., eg Ditylenchus dipsaci, Dolichodorus spp., Globodera spp., eg Globodera pallida, Globodera rostochiensis, Helicotylenchus spp., eg Helicotylenchus dihystera, Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., eg Heterodera avenae, Heterodera glycines, Heterodera schachtii, Hoplolaimus spp., Longidorus spp , eg Longidorus africanus, Meloidogyne spp., eg Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paraphelenchus spp., Paratrichodorus spp., eg Paratrichodorus minor, Pratylenchus spp. , eg Pratylenchus penetrans, Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., eg Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp., eg Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., eg Tylenchorhynchus annulatus, Tylenchulus spp., eg Tylenchulus semipenetrans, Xiphinema spp ., eg Xiphinema index. Furthermore, the order of the coccidia, eg Eimeria spp., Can be determined from the sub-region of the protozoa. fight.
Die Verbindungen der Formel (I) können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide, Safener, Wachstums-'regulatoren oder Mittel zur Verbesserung der Pflanzeneigenschaften, als Mikrobizide oder Gametozide, beispielsweise als Fungizide, Antimykotika, Bakterizide, Virizide (einschließlich Mittel gegen Viroide) oder als Mittel gegen MLO (Mycoplasma- like-organism) und RLO (Rickettsia- like-organism) verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen. The compounds of the formula (I) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, viricides (including agents against Viroids) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Formulierungen formulations
Die vorliegende Erfindung betrifft weiterhin Formulierungen und daraus bereitete Anwendungsformen als Schädlingsbekämpfungsmittel wie z. B. Drench-, Drip- und Spritzbrühen, umfassend mindestens eine Verbindung der Formel (I). Gegebenenfalls enthalten die Anwendungsformen weitere Schädlingsbekämpfungsmittel und/oder die Wirkung verbessernde Adjuvantien wie Penetrationsforderer, z. B. vegetative Öle wie beispielsweise Rapsöl, Sonnenblumenöl, Mineralöle wie beispielsweise Paraffinöle, Alkylester vegetativer Fettsäuren wie beispielsweise Rapsöl- oder Sojaölmethylester oder Alkanol-alkoxylate und/oder Spreitmittel wie beispielsweise Alkylsiloxane und/oder Salze z.B. organische oder anorganische Ammonium- oder Phosphoniumsalze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat und/oder die Retention fordernde Mittel wie z. B. Dioctylsulfosuccinat oder Hydroxypropyl-guar Polymere und/oder Humectants wie z.B. Glycerin und/oder Dünger wie beispielsweise Ammonium-, Kalium- oder Phosphor-enthaltende Dünger. The present invention further relates to formulations and application forms prepared therefrom as pesticides such. B. drench, drip and spray liquors, comprising at least one compound of formula (I). Optionally, the use forms contain other pesticides and / or the effect of improving adjuvants such as Penetrationsforderer, z. As vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetable fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts such as organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-demanding agents such as. As dioctylsulfosuccinate or hydroxypropyl guar polymers and / or humectants such as glycerol and / or fertilizers such as ammonium, potassium or Phosphorus-containing fertilizer.
Übliche Formulierungen sind beispielsweise wasserlösliche Flüssigkeiten (SL), Emulsionskonzentrate (EC), Emulsionen in Wasser (EW), Suspensionskonzentrate (SC, SE, FS, OD), in Wasser dispergierbare Granulate (WG), Granulate (GR) und Kapselkonzentrate (CS); diese und weitere mögliche Formuliertypen sind beispielsweise durch Crop Life International und in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576 beschrieben. Gegebenenfalls enthalten die Formulierungen neben einem oder mehreren Verbindungen der Formel (I) weitere agrochemische Wirkstoffe. Vorzugsweise handelt es sich um Formulierungen oder Anwendungsformen, welche Hilfsstoffe wie beispielsweise Streckmittel, Lösemittel, Spontanitätsförderer, Trägerstoffe, Emulgiermittel, Dispergiermittel, Frostschutzmittel, Biozide, Ver dicker und/oder weitere Hilfsstoffe wie beispielsweise Adjuvantien enthalten. Ein Adjuvant in diesem Kontext ist eine Komponente, die die biologische Wirkung der Formulierung verbessert, ohne dass die Komponente selbst eine biologische Wirkung hat. Beispiele für Adjuvantien sind Mittel, die die Retention, das Spreitverhalten, das Anhaften an der Blattoberfläche oder die Penetration fördern. Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ; These and other possible formulation types are described, for example, by Crop Life International and in Pesticide Specifications, Manual on Development and Use of FAO and WHO Specifications for Pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. If appropriate, the formulations contain, in addition to one or more compounds of the formula (I), further agrochemical active substances. Preferably, they are formulations or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further adjuvants such as adjuvants. An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect. Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Verbindungen der Formel (I) mit Hilfsstoffen wie beispielsweise Streckmitteln, Lösemitteln und/oder festen Trägerstoffen und/oder weiteren Hilfsstoffen wie beispielsweise oberflächenaktive Stoffe. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. These formulations are prepared in a known manner, e.g. by mixing the compounds of the formula (I) with auxiliaries, such as, for example, extenders, solvents and / or solid carriers and / or further auxiliaries, for example surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.
Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, der Formulierung der Verbindungen der Formel (I) oder den aus diesen Formulierungen bereiteten Anwendungsformen (wie z.B. gebrauchsfähigen Schädlingsbekämpfungsmitteln wie Spritzbrühen oder Saatgutbeizen) besondere Eigenschaften, wie bestimmte physikalische, technische und/oder biologische Eigenschaften zu verleihen. Excipients which can be used are those which are suitable for the formulation of the compounds of the formula (I) or the use forms prepared from these formulations (such as, for example, ready-to-use pesticides such as spray liquors or seed dressings), such as certain physical, technical and / or biological properties To give properties.
Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsulfoxid). As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösemittel verwendet werden. Als flüssige Lösemittel kommen im Wesentlichen infrage: Aromaten wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasser-stoffe wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylformamid und Dimethylsulfoxid sowie Wasser. In the case of the use of water as an extender, for example, organic solvents as Auxiliary solvents can be used. Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
Grundsätzlich können alle geeigneten Lösemittel verwendet werden. Geeignete Lösemittel sind beispielsweise aromatische Kohlenwasserstoffe wie z.B. Xylol, Toluol oder Alkylnaphthaline, chlorierte aromatische oder aliphatische Kohlenwasserstoffe wie z.B. Chlorbenzol, Chlorethylen, oder Methylenchlorid, aliphatische Kohlenwasserstoffe wie z.B. Cyclohexan, Paraffine, Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole wie z.B. Methanol, Ethanol, iso-Propanol, Butanol oder Glykol sowie deren Ether und Ester, Ketone wie z.B. Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösemittel wie Dimethylsulfoxid sowie Wasser. Grundsätzlich können alle geeigneten Trägerstoffe eingesetzt werden. Als Trägerstoffe kommen insbesondere infrage: z.B. Ammoniumsalze und natürliche Gesteinsmehle wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehl, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse und /oder feste Düngemittel. Mischungen solcher Trägerstoffe können ebenfalls verwendet werden. Als Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Papier, Kokosnussschalen, Maiskolben und Tabakstängel. In principle, all suitable solvents can be used. Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water. In principle, all suitable carriers can be used. Suitable carriers are, in particular: Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Suitable carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
Auch verflüssigte gasförmige Streckmittel oder Lösemittel können eingesetzt werden. Insbesondere eignen sich solche Streckmittel oder Trägerstoffe, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Also, liquefied gaseous diluents or solvents can be used. Particularly suitable are those diluents or carriers which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
Beispiele für Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe sind Salze von Polyacrylsäure, Salze von Lignosulphonsäure, Salze von Phenolsulphonsäure oder Naphthalinsulphonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, mit substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulphobernsteinsäureestern, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenole, Fettsäureester von Polyolen und Derivate der Verbindungen enthaltend Sulphate, Sulphonate und Phosphate, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate, Eiweißhydrolysate, Lignin-Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist vorteilhaft, wenn eine der Verbindungen der Formel (I) und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates, protein hydrolysates, lignin-sulphite liquors and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of formula (I) and / or one of the inert carriers is not soluble in water and when applied in water.
Als weitere Hilfsstoffe können in den Formulierungen und den daraus abgeleiteten Anwendungsformen Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Nähr- und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink vorhanden sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Konservierungsmittel, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Weiterhin enthalten sein können schaumerzeugende Mittel oder Entschäumer. As further adjuvants, in the formulations and the applications derived therefrom, dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
Ferner können die Formulierungen und daraus abgeleiteten Anwendungsformen als zusätzliche Hilfsstoffe auch Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere enthalten wie Gummiarabikum, Polyvinylalkohol, Polyvinylacetat sowie natürliche Phospholipide wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Hilfsstoffe können mineralische und vegetabile Öle sein. In addition, the formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other auxiliaries may be mineral and vegetable oils.
Gegebenenfalls können noch weitere Hilfsstoffe in den Formulierungen und den daraus abgeleiteten Anwendungsformen enthalten sein. Solche Zusatzstoffe sind beispielsweise Duftstoffe, schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Retentionsförderer, Stabilisatoren, Sequestiermittel, Komplexbildner, Humectans, Spreitmittel. Im Allgemeinen können die Verbindungen der Formel (I) mit jedem festen oder flüssigen Zusatzstoff, welches für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Optionally, further auxiliaries may be present in the formulations and in the use forms derived therefrom. Such additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents. In general, the compounds of formula (I) may be combined with any solid or liquid additive commonly used for formulation purposes.
Als Retentionsförderer kommen alle diejenigen Substanzen in Betracht, die die dynamische Oberflächenspannung verringern wie beispielsweise Dioctylsulfosuccinat oder die die Visko-Elastizität erhöhen wie beispielsweise Hydroxypropyl-guar Polymere. As retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
Als Penetrationsförderer kommen im vorliegenden Zusammenhang alle diejenigen Substanzen in Betracht, die üblicherweise eingesetzt werden, um das Eindringen von agrochemischen Wirkstoffen in Pflanzen zu verbessern. Penetrationsförderer werden in diesem Zusammenhang dadurch definiert, dass sie aus der (in der Regel wässerigen) Applikationsbrühe und/oder aus dem Spritzbelag in die Kutikula der Pflanze eindringen und dadurch die Stoffbeweglichkeit (Mobilität) der Wirkstoffe in der Kutikula erhöhen können. Die in der Literatur (Baur et al., 1997, Pesticide Science 51, 131-152) beschriebene Methode kann zur Bestimmung dieser Eigenschaft eingesetzt werden. Beispielhaft werden genannt Alkoholalkoxylate wie beispielsweise Kokosfettethoxylat (10) oder Isotridecylethoxylat (12), Fettsäureester wie beispielsweise Rapsöl- oder Sojaölmethylester, Fettamine Alkoxylate wie beispielsweise Tallowamine-ethoxylat (15) oder Ammonium- und/oder Phosphonium-Salze wie beispielsweise Ammoniumsulfat oder Diammonium-hydrogenphosphat. Die Formulierungen enthalten bevorzugt zwischen 0,00000001 und 98 Gew.-% der Verbindung der Formel (I), besonders bevorzugt zwischen 0,01 und 95 Gew.-% der Verbindung der Formel (I), ganz besonders bevorzugt zwischen 0,5 und 90 Gew.-% der Verbindung der Formel (I), bezogen auf das Gewicht der Formulierung. Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants. Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle. The method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152) can be used to determine this property. Examples are called Alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate. The formulations preferably contain between 0.00000001 and 98 wt .-% of the compound of formula (I), more preferably between 0.01 and 95 wt .-% of the compound of formula (I), most preferably between 0.5 and 90% by weight of the compound of formula (I), based on the weight of the formulation.
Der Gehalt an der Verbindung der Formel (I) in den aus den Formulierungen bereiteten Anwendungsformen (insbesondere Schädlingsbekämpfungsmittel) kann in weiten Bereichen variieren. Die Konzentration der Verbindung der Formel (I) in den Anwendungsformen kann üblicherweise zwischen 0,00000001 und 95 Gew.-% der Verbindung der Formel (I), vorzugsweise zwischen 0,00001 und 1 Gew.-%, bezogen auf das Gewicht der Anwendungsform, liegen. Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise. Mischungen The content of the compound of the formula (I) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges. The concentration of the compound of the formula (I) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the formula (I), preferably between 0.00001 and 1% by weight, based on the weight of the application form , lie. The application is done in a custom forms adapted to the application. mixtures
Die Verbindungen der Formel (I) können auch in Mischung mit einem oder mehreren geeigneten Fungiziden, Bakteriziden, Akariziden, Molluskiziden, Nematiziden, Insektiziden, Mikrobiologika, Nützlingen, Herbizide, Düngemitteln, Vogelrepellentien, Phytotonics, Sterilantien, Safenern, Semiochemicals und/oder Pflanzenwachstumsregulatoren verwendet werden, um so z.B. das Wirkungsspektrum zu verbreitern, die Wirkdauer zu verlängern, die Wirkgeschwindigkeit zu steigern, Repellenz zu verhindern oder Resistenzentwicklungen vorzubeugen. Desweiteren können solche Wirkstoffkombinationen das Pflanzenwachstum und/oder die Toleranz gegenüber abiotischen Faktoren wie z. B. hohen oder niedrigen Temperaturen, gegen Trockenheit oder gegen erhöhten Wasser- bzw. Bodensalzgehalt verbessern. Auch lässt sich das Blüh- und Fruchtverhalten verbessern, die Keimfähigkeit und Bewurzelung optimieren, die Ernte erleichtern und Ernteerträge steigern, die Reife beeinflussen, die Qualität und/oder den Ernährungswert der Ernteprodukte steigern, die Lagerfähigkeit verlängern und/oder die Bearbeitbarkeit der Ernteprodukte verbessern. The compounds of formula (I) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators be, for example to widen the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-exposure or to prevent the development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. As high or low temperatures, improve against dryness or increased water or Bodensalzgehalt. Also, flowering and fruiting behavior can be improved, germination and rooting can be improved, harvesting and crop yields increased, maturity can be enhanced, crop quality and / or nutritional value increased, shelf life extended and / or crop productivity improved.
Weiterhin können die Verbindungen der Formel (I) in Mischung mit weiteren Wirkstoffen oder Semiochemicals, wie Lockstoffen und/oder Vogelrepellentien und/oder Pflanzenaktivatoren und/oder Wachstumsregulatoren und/oder Düngemitteln vorliegen. Gleichfalls können die Verbindungen der Formel (I) in Mischungen mit Mitteln zur Verbesserung der Pflanzeneigenschaften wie zum Beispiel Wuchs, Ertrag und Qualität des Erntegutes eingesetzt werden. In einer besonderen erfindungsgemäßen Ausführungsform liegen die Verbindungen der Formel (I) in Formulierungen bzw. in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit weiteren Verbindungen vor, vorzugsweise solchen wie nachstehend beschrieben. Furthermore, the compounds of the formula (I) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula (I) can be used in mixtures with agents for improving plant properties such as, for example, growth, yield and quality of the crop. In a particular embodiment of the invention, the compounds of the formula (I) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
Wenn eine der im Folgenden genannten Verbindungen in verschiedenen tautomeren Formen vorkommen kann sind auch diese Formen mit umfasst, auch wenn sie sie nicht in jedem Fall explizit genannt wurden. Als Mischpartner kommen zum Beispiel die folgenden Verbindungen in Betracht: If one of the following compounds can occur in different tautomeric forms, these forms are also included, even if they were not explicitly mentioned in each case. Suitable mixing partners are, for example, the following compounds:
Insektizide / Akarizide / Nematizide: Insecticides / acaricides / nematicides:
Die hier mit ihrem „common name" genannten Wirkstoffe sind bekannt und beispielsweise im Pestizidhandbuch („The Pesticide Manual" 16th Ed., British Crop Protection Council 2012) beschrieben oder im Internet recherchierbar (z.B. http://www.alanwood.net/pesticides). The active substances mentioned here with their "common name" are known and described, for example, in the Pesticide Handbook ("The Pesticide Manual" 16th ed., British Crop Protection Council 2012) or searchable on the Internet (eg http://www.alanwood.net/pesticides ).
(1) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder organophosphate, z.B. Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B. Chlordane und Endosulfan oder Phenylpyrazole (Fiprole), z.B. Ethiprole und Fipronil. (1) Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and Xylylcarb or organophosphates, eg Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Disulfone, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O- (methoxyaminothio-phosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methidathione, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, triclorfone and vamidothion. (2) GABA-controlled chloride channel antagonists, such as cyclodiene organochlorines, e.g. Chlordanes and endosulfan or phenylpyrazoles (fiproles), e.g. Ethiprole and fipronil.
(3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl Isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta- Cypermethrin, theta-Cypermethrin, zeta-Cypermethrin, Cyphenothrin [(lR)-trans-Isomere], Deltamethrin, Empenthrin [(EZ)-(lR)-Isomere), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(lR)-trans- Isomer), Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)- Isomere)], Tralomethrin und Transfluthrin oder DDT oder Methoxychlor. (3) sodium channel modulators / voltage dependent sodium channel blockers such as pyrethroids, eg acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin , Cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) -trans isomers], deltamethrin, empenthrin [ (EZ) - (lR) -isomers), esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin, tau-fluvalinates, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(lR) -trans- Isomer), prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) - isomers)], tralomethrin and transfluthrin or DDT or methoxychlor.
(4) Nikotinerge Acetylcholin-Rezeptor (nAChR) Agonisten, wie beispielsweise Neonikotinoide, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid und Thiamethoxam oder Nikotin oder Sulfoxaflor. (4) nicotinergic acetylcholine receptor (nAChR) agonists such as neonicotinoids, e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.
(5) Nikotinerge Acetylcholin-Rezeptor (nAChR) allosterische Aktivatoren, wie beispielsweise Spinosine, z.B. Spinetoram und Spinosad. (5) nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
(6) Chlorid-Kanal-Aktivatoren, wie beispielsweise Avermectine/Milbemycine, z.B. Abamectin, Emamectin-benzoat, Lepimectin und Milbemectin. (7) Juvenilhormon-Imitatoren, wie beispielsweise Juvenilhormon- Analoge, z.B. Hydroprene, Kinoprene und Methoprene oder Fenoxycarb oder Pyriproxyfen. (6) chloride channel activators, such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin. (7) Juvenile hormone mimics, such as juvenile hormone analogs, e.g. Hydroprene, Kinoprene and Methoprene or Fenoxycarb or Pyriproxyfen.
(8) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise (8) agents with unknown or non-specific mechanisms of action, such as
Alkylhalide, z.B. Methylbromid und andere Alkylhalide; oderChloropicrin oder Sulfurylfluorid oder Borax oder Brechweinstein. (9) Selektive Fraßhemmer, z.B. Pymetrozine oder Flonicamid. Alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic. (9) Selective feeding inhibitors, e.g. Pymetrozine or flonicamide.
(10) Milbenwachstumsinhibitoren, z.B. Clofentezine, Hexythiazox und Diflovidazin oder Etoxazole. (10) mite growth inhibitors, e.g. Clofentezine, hexythiazox and diflovidazine or etoxazole.
(11) Mikrobielle Disruptoren der Insektendarmmembran, z.B. Bacillus thuringiensis Subspezies israelensis, Bacillus sphaericus, Bacillus thuringiensis Subspezies aizawai, Bacillus thuringiensis Subspezies kurstaki, Bacillus thuringiensis Subspezies tenebrionis und BT Pflanzenproteine: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl . (11) Insect intestinal membrane microbial disruptors, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
(12) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron oder Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin und Fenbutatin-oxid oder Propargite oder Tetradifon. (12) oxidative phosphorylation inhibitors, ATP disruptors such as diafenthiuron or organotin compounds, e.g. Azocyclotin, Cyhexatin and Fenbutatin-oxide or Propargite or Tetradifon.
(13) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten, wie beispielsweise Chlorfenapyr, DNOC und Sulfluramid. (13) Decoupling of oxidative phosphorylation by interruption of the H proton gradient, such as chlorfenapyr, DNOC, and sulfluramide.
(14) Nikotinerge Acetylcholin-Rezeptor- Antagonisten, wie beispielsweise Bensultap, Cartap-hydrochlorid, Thiocyclam und Thiosultap-Natrium. (15) Inhibitoren der Chitinbiosynthese, Typ 0, wie beispielsweise Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron und Triflumuron. (14) Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium. (15) Type 0 inhibitors of chitin biosynthesis, such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
(16) Inhibitoren der Chitinbiosynthese, Typ 1, wie beispielsweise Bupro fezin. (17) Häutungshemmer (insbesondere bei Dipteren, d.h.Zweiflüglern), wie beispielsweise Cyromazine. (16) inhibitors of chitin biosynthesis, type 1, such as Bupro fezin. (17) Anti-skinning agents (especially in dipterans, i.e., two-toed), such as Cyromazine.
(18) Ecdyson-Rezeptor Agonisten, wie beispielsweise Chromafenozide, Halofenozide, Methoxyfenozide und Tebufenozide. (18) ecdysone receptor agonists, such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
(19) Oktopaminerge Agonisten, wie beispielsweise Amitraz. (19) Octopaminergic agonists, such as amitraz.
(20) Komplex-III-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon oder Acequinocyl oder Fluacrypyrim. (20) Complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
(21) Komplex-I-Elektronentransportinhibitoren, beispielsweise METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad und Tolfenpyrad oder Rotenone (Derris). (21) complex I electron transport inhibitors, for example, METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
(22) Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb oder Metaflumizone. (22) voltage dependent sodium channel blockers, e.g. Indoxacarb or metaflumizone.
(23) Inhibitoren der Acetyl-CoA-Carboxylase, wie beispielsweise Tetron- und Tetramsäurederivate, z.B. Spirodiclofen, Spiromesifen und Spirotetramat. (23) inhibitors of acetyl-CoA carboxylase, such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
(24) Komplex-IV-Elektronentransportinhibitoren, wie beispielsweise Phosphine, z.B. Aluminiumphosphid, Calciumphosphid, Phosphin und Zinkphosphid oder Cyanid. (24) complex IV electron transport inhibitors such as phosphines, e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.
(25) Komplex-II-Elektronentransportinhibitoren, wie beispielsweise Cyenopyrafen und Cyflumetofen. (25) Complex II electron transport inhibitors such as cyenopyrafen and cyflumetofen.
(28) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Chlorantraniliprole, Cyantraniliprole und Flubendiamide, weitere Wirkstoffe wie beispielsweise Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, (28) ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide, other active substances such as Afidopyropen, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite,
Dicofol, Diflovidazin, Fluensulfone, Flometoquin, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenozide, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyrifluquinazon, Pyriminostrobin, Tetramethylfluthrin und Iodmethan; desweiteren Präparate auf Basis von Bacillus firmus (1-1582, BioNeem, Votivo) , sowie folgende Verbindungen:3- Brom-N- {2-brom-4-chlor-6- [( 1 -cyclopropylethyl)carbamoyl]phenyl} - 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol- 5-carboxamid (bekannt aus WO2005/077934) und l- {2-Fluor-4-methyl-5-[(2,2,2- trifluorethyl)sulfinyl]phenyl}-3-(trifluormethyl)-lH-l,2,4-triazol-5-amin (bekannt aus WO2006/043635), { 1 '- [(2E)-3 -(4-Chlorphenyl)prop-2-en- 1 -yl] -5-fluorspiro [indol-3 ,4'-piperidin] - 1 (2H)-yl} (2-chlorpyridin-4- yl)methanon (bekannt aus WO2003/106457), 2-Chlor-N-[2-{l-[(2E)-3-(4-chlorphenyl)prop-2-en-l- yl]piperidin-4-yl}-4-(trifluormethyl)phenyl]isonicotinamid (bekannt aus WO2006/003494), 3-(2,5- Dimethylphenyl)-4-hydroxy-8-methoxy-l,8-diazaspiro[4.5]dec-3-en-2-on (bekannt aus WO2009/049851), 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-l,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonat (bekannt aus WO2009/049851), 4-(But-2-in-l-yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluorpyrimidin (bekannt aus WO2004/099160), 4-(But-2-in-l-yloxy)-6-(3-chlorphenyl)pyrimidin (bekannt aus WO2003/076415), PF1364 (CAS-Reg.No. 1204776-60-2), 4-[5-(3,5-Dich^henyl)-5-(trifluormethyl)-4,5-dihydro-l,2- oxazol-3-yl]-2-methyl-N- {2-oxo-2-[(2,2,2-trifluorethyl)amino]ethyl}benzamid (bekannt aus WO2005/085216), 4- {5-[3-Chlor-5-(trifluomiethyl)phenyl]-5-(trifluormethyl)-4,5-dihydro-l,2-oxazol-3^ yl}-N- {2-0X0-2- [(2,2,2-trifluorethyl)amino]ethyl}-l-naphthamid (bekannt aus WO2009/002809), Methyl- 2- [2-( { [3 -brom- 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol-5-yl]carbonyl} amino)-5-chlor-3 -methylbenzoyl] -2- methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[2-({[3-brom-l-(3-chlorpyridin-2- yl)-lH-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2- [2-( { [3 -brom- 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol-5-yl]carbonyl} amino)-5- cyan-3 -methylbenzoyl] -2-methylhydrazincarboxylat (bekannt aus WO2005/085216), Methyl-2-[3,5- dibrom-2-( { [3 -brom- 1 -(3 -chlorpyridin-2-yl)- 1 H-pyrazol-5-yl]carbonyl} amino)benzoyl] -2- ethylhydrazincarboxylat (bekannt aus WO2005/085216), l-(3-Chlorpyridin-2-yl)-N-[4-cyan-2-methyl-6- (methylcarbamoyl)phenyl]-3- {[5-(trifluormethyl)-2H-tetrazol-2-yl]methyl}-lH-pyrazol-5-carboxamid (bekannt aus WO2010/069502), N- [2-(5-Amino- 1 ,3 ,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl] -3 -brom- 1 - (3-chlorpyridin-2-yl)-lH-pyrazol-5-carboxamid (bekannt aus CN102057925), 3-Chlor-N-(2-cyanpropan- 2-yl)-N- [4-( 1 , 1 , 1 ,2,3,3 ,3 -heptafluorpropan-2-yl)-2-methylphenyl]phthalamid (bekannt ausDicofol, Diflovidazine, Fluensulfone, Flometoquine, Flufenerim, Flufenoxystrobin, Flufiprole, Fluopyram, Flupyradifurone, Fufenocide, Heptafluthrin, Imidaclothiz, Iprodione, Meperfluthrin, Paichongding, Pyflubumide, Pyrifluquinazone, Pyriminostrobin, Tetramethylfluthrin and Iodomethane; furthermore preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following compounds: 3-bromo-N- {2-bromo-4-chloro-6- [(1-cyclopropyl-ethyl) -carbamoyl] -phenyl} -1 - (3-chloropyridin-2-yl) -1 H -pyrazole-5-carboxamide (known from WO2005 / 077934) and 1- {2-fluoro-4-methyl-5 - [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from WO2006 / 043635), {1 '- [(2E) -3- (4-Chloro-phenyl) -prop-2-en-1-yl] -5-fluorospiro [indole-3, 4'-piperidine] -1 (2H) -yl} (2 -chloropyridin-4-yl) methanone (known from WO2003 / 106457), 2-chloro-N- [2- {1 - [(2E) -3- (4-chlorophenyl) -prop-2-en-1-yl] piperidin-4-yl} -4- (trifluoromethyl) phenyl] isonicotinamide (known from WO2006 / 003494), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diazaspiro [4.5] dec 3-en-2-one (known from WO2009 / 049851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1,8-diazaspiro [4.5] dec-3-ene-4 yl ethyl carbonate (known from WO2009 / 049851), 4- (but-2-yn-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO2004 / 099160), 4- (But-2-yn-1-yloxy) -6- (3-chlorophenyl) pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), 4- [5- (3,5-dichloro) -5- (trifluoromethyl) -4,5-dihydro-1, 2-oxazol-3-yl] -2-methyl-N- {2-oxo-2 - [(2, 2,2-trifluoroethyl) amino] ethyl} benzamide (known from WO2005 / 085216), 4- {5- [3-chloro-5- (trifluoromethyl) phenyl] -5- (trifluoromethyl) -4,5-dihydro-1 , 2-oxazol-3-yl} -N- {2-0X0-2- [( 2,2,2-trifluoroethyl) amino] ethyl} -l-naphthamide (known from WO2009 / 002809), methyl 2- [2- ({[3-bromo-1 - (3-chloropyridin-2-yl) - 1 H-pyrazol-5-yl] carbonyl} amino) -5-chloro-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [2 - ({[3-bromo-1-yl] (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [2- ({[3-Bromo-1 - (3-chloropyridin-2-yl) -1 H -pyrazol-5-yl] carbonyl} amino) -5-cyano-3-methylbenzoyl] -2-methylhydrazinecarboxylate (known from WO2005 / 085216), methyl 2- [3,5-dibromo-2- ({[3-bromo-1 - (3-chloropyridin-2-yl) -1 H -pyrazol-5-yl] carbonyl} amino) benzoyl] -2-ethylhydrazinecarboxylate (known from WO2005 / 085216), 1- (3-chloropyridin-2-yl) -N- [4-cyano-2-methyl-6- (methylcarbamoyl) phenyl] -3- {[5- (5) trifluoromethyl) -2H-tetrazol-2-yl] methyl} -1H-pyrazole-5-carboxamide (known from WO2010 / 069502), N- [2- (5-amino-1,3,3,4-thiadiazol-2-yl ) -4-chloro-6-methylphenyl] -3-bromo-1 - (3-chloro rpyridin-2-yl) -1H-pyrazole-5-carboxamide (known from CN102057925), 3-chloro-N- (2-cyanopropan-2-yl) -N- [4- (1,1,1,2, 3,3,3-heptafluoropropan-2-yl) -2-methylphenyl] phthalamide (known from
WO2012/034472), 8-Chlor-N-[(2-chlor-5-methoxyphenyl)sulfonyl]-6-(trifluormethyl)imidazo[l,2- a]pyridin-2-carboxamid (bekannt aus WO2010/129500), 4-[5-(3,5-Dich^henyl)-5-(trifluormethyl)-4,5- dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l-oxidothietan-3-yl)benzamid (bekannt aus WO2009/080250), 4- [5-(3,5-Dichlo^henyl)-5-(trifluormethyl)-4,5-dihydro-l,2-oxazol-3-yl]-2-methyl-N-(l-oxM^ WO2012 / 034472), 8-chloro-N - [(2-chloro-5-methoxyphenyl) sulfonyl] -6- (trifluoromethyl) imidazo [1,2-a] pyridine-2-carboxamide (known from WO2010 / 129500), 4- [5- (3,5-dichloro) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- (1-oxidothietane-3 -yl) benzamide (known from WO2009 / 080250), 4- [5- (3,5-dichloro-1-yl-yl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] - 2-methyl-N- (l-OXM ^
yl)benzamid (bekannt aus WO2012/029672), l-[(2-Chlor-l,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H- pyrido[l,2-a]pyrimidin-l-ium-2-olat (bekannt aus WO2009/099929), l-[(6-Chlorpyridin-3-yl)methyl]-4- oxo-3-phenyl-4H-pyrido[l,2-a]pyrimidin-l-ium-2-olat (bekannt aus WO2009/099929), (5S,8R)-l-[(6- Chlo^yridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-lH-5,8-epoxyimidazo[l,2-a]azepin (bekannt aus WO2010/ 069266), (2E)- 1 - [(6-Chlorpyridin-3 -yl)methyl] -N'-nitro-2-pentylidenhydrazincarboximidamid (bekannt aus WO2010/060231), 4-(3-{2,6-Dichlor-4-[(3,3-dichloφrop-2-en-l-yl)oxy]phenoxy}propoxy)- 2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN101337940), N-[2-(tert-Butylcarbamoyl)-4-chlor- 6-methylphenyl] - 1 -(3 -chlorpyridin-2-yl)-3 -(fluormethoxy)- 1 H-pyrazol-5-carboxamid (bekannt aus WO2008/134969). yl) benzamide (known from WO2012 / 029672), 1 - [(2-chloro-1,3-thiazol-5-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-l-ium-2-olate (known from WO2009 / 099929), l - [(6-chloropyridin-3-yl) methyl] -4-oxo-3-phenyl-4H-pyrido [1,2-a] pyrimidin-l-ium-2-olate (known from WO2009 / 099929), (5S, 8R) -1 - [(6-chloro-3-yl) methyl] -9-nitro-2,3,5, 6,7,8-hexahydro-1H-5,8-epoxyimidazo [1,2-a] azepine (known from WO2010 / 069266), (2E) - 1 - [(6-chloropyridin-3-yl) methyl] - N'-nitro-2-pentylidenehydrazinecarboximidamide (known from WO2010 / 060231), 4- (3- {2,6-dichloro-4 - [(3,3-dichloφrop-2-en-1-yl) oxy] phenoxy} propoxy) -2-methoxy-6- (trifluoromethyl) pyrimidine (known from CN101337940), N- [2- (tert-butylcarbamoyl) -4-chloro-6-methylphenyl] -1- (3-chloropyridin-2-yl) 3 - (fluoromethoxy) -1 H -pyrazole-5-carboxamide (known from WO2008 / 134969).
Fungizide Die hier mit ihrem "common name" spezifizierten Wirkstoffe sind bekannt, beispielsweise beschrieben im "Pesticide Manual" oder im Internet (beispielsweise: http://www.alanwood.net/pesticides). fungicides The active ingredients specified here with their "common name" are known, for example, described in the "Pesticide Manual" or on the Internet (for example: http://www.alanwood.net/pesticides).
(1) Inhibitoren der Ergosterol-Biosynthese, wie beispielsweise (1.1) Aldimorph, (1.2) Azaconazol, (1.3) Bitertanol, (1.4) Bromuconazol, (1.5) Cyproconazol, (1.6) Diclobutrazol, (1.7) Difenoconazol, (1.8) Diniconazol, (1.9) Diniconazol-M, (1.10) Dodemorph, (1.11) Dodemorph Acetat, (1.12) Epoxiconazol, (1.13) Etaconazol, (1.14) Fenarimol, (1.15) Fenbuconazol, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinconazol, (1.20) Flurprimidol, (1.21) Flusilazol, (1.22) Flutriafol, (1.23) Furconazol, (1.24) Furconazol-Cis, (1.25) Hexaconazol, (1.26) Imazalil, (1.27) Imazalil Sulfat, (1.28) Imibenconazol, (1.29) Ipconazol, (1.30) Metconazol, (1.31) Myclobutanil, (1.32) Naftifin, (1.33) Nuarimol, (1.34) Oxpoconazol, (1.35) Paclobutrazol, (1.36) Pefurazoat, (1.37) Penconazol, (1.38) Piperalin, (1.39) Prochloraz, (1.40) Propiconazol, (1.41) Prothioconazol, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazol, (1.45) Simeconazol, (1.46) Spiroxamin, (1.47) Tebuconazol, (1.48) Terbinafm, (1.49) Tetraconazol, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizol, (1.54) Triforin, (1.55) Triticonazol, (1.56) Uniconazol, (1.57) Uniconazol-p, (1.58) Viniconazol, (1.59) Voriconazol, (1.60) l-(4-Chlorphenyl)-2-(lH-l,2,4-triazol-l-yl)cycloheptanol, (1.61) Methyl- 1 -(2,2- dimethyl-2,3 -dihydro- 1 H-inden- 1 -yl)-l H-imidazol-5-carboxylat, ( 1.62) N'- {5-(Difluormethyl)-2-methyl-4- [3-(trimethylsilyl)propoxy]phenyl} -N-ethyl-N-methylimidoformamid, (1.63) N-Ethyl-N-methyl-N'- {2- methyl-5-(trifluormethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamid und (1.64) 0-[l-(4- Methoxyphenoxy)-3,3-dimethylbutan-2-yl]-lH-imidazol-l -carbothioat, (1.65) Pyrisoxazole. (2) Inhibitoren der Respiration (Atmungsketten-Inhibitoren), wie beispielsweise (2.1) Bixafen, (2.2) Boscalid, (2.3) Carboxin, (2.4) Diflumetorim, (2.5) Fenfuram, (2.6) Fluopyram, (2.7) Flutolanil, (2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mischung des syn-epimeren Razemates 1RS,4SR,9RS und des anti-empimeren Razemates 1RS,4SR,9SR, (2.12) Isopyrazam (anti- epimeres Razemat ), (2.13) Isopyrazam (anti-epimeres Enantiomer 1R,4S,9S), (2.14) Isopyrazam (anti- epimeres Enantiomer 1S,4R,9R), (2.15) Isopyrazam (syn-epimeres Razemat 1RS,4SR,9RS), (2.16) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.17) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.18) Mepronil, (2.19) Oxycarboxin, (2.20) Penflufen, (2.21) Penthiopyrad, (2.22) Sedaxane, (2.23) Thifluzamid, (2.24) 1 -Methyl-N- [2-( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] -3 -(trifluormethyl)- 1 H-pyrazol-4- carboxamid, (2.25) 3-(Difluormethyl)- 1 -methyl-N- [2-( 1 , 1 ,2,2-tetrafluorethoxy)phenyl] - 1 H-pyrazol-4- carboxamid, (2.26) 3 -(Difluormethyl)-N- [4-fluor-2-( 1 , 1 ,2,3,3,3-hexafluorpropoxy)phenyl] - 1 -methyl- 1 H- pyrazol-4-carboxamid, (2.27) N-[l-(2,4-Dichlorphenyl)-l-methoxypropan-2-yl]-3-(difluormethyl)-l- methyl-lH-pyrazol-4-carboxamid, (2.28) 5,8-Difluor-N-[2-(2-fluor-4-{[4-(trifluormethyl)pyridin-2- yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.29) Benzovindiflupyr, (2.30) N-[(lS,4R)-9-(Dichlormethylen)- l,2,3,4-tetrahydro-l,4-methanonaphthalen-5-yl]-3-(difluormethyl)-l-methyl-lH-pyrazol-4-carboxamid und (2.31) N- [(1 R,4S)-9-(Dichlormethylen)- 1 ,2,3,4-tetrahydro- 1 ,4-methanonaphthalen-5-yl] -3 -(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (2.32) 3 -(Difluormethyl)- 1 -methyl-N-(l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H- inden-4-yl)-lH-pyrazol-4-carboxamid, (2.33) l,3,5-Trimethyl-N-(l,l,3-rrimethyl-2,3-dihydro-lH-inden-4- yl)-lH-pyrazol-4-carboxamid, (2.34) l-Methyl-3-(trifluormethyl)-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden- 4-yl)- 1 H-pyrazol-4-carboxamid, (2.35) 1 -Methyl-3 -(trifluormethyl)-N- [(3R)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- lH-inden-4-yl]- lH-pyrazol-4-carboxamid, (2.36) 1 -Methyl-3-(trifluormethyl)-N-[(3S)- 1 , 1 ,3-trimethyl-2,3- dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.37) 3-(Difluormethyl)-l-methyl-N-[(3S)-l,l,3- rrimethyl-2,3-dihydro-lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.38) 3-(Difluormethyl)-l-methyl-N- [(3R)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.39) 1 ,3,5-Trimethyl-N- [(3R)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, (2.40) 1 ,3,5-Trimethyl-N- [(3 S)- 1,1, 3 -trimethyl-2,3 -dihydro- lH-inden-4-yl]-lH-pyrazol-4-carboxamid, (2.41) Benodanil, (2.42) 2- Chlor-N-(l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl)pyridine-3-carboxamid, (2.43) Isofetamid (1) inhibitors of ergosterol biosynthesis, such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole , (1.9) Diniconazole-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) etaconazole, (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidine, ( 1.18) fenpropimorph, (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) furconazole, (1.24) furconazole cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil Sulphate, (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37) Penconazole, (1.38) piperalin, (1.39) prochlorazole, (1.40) propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) quinconazole, (1.45) simeconazole, (1.46) spiroxamine, (1.47) Tebuconazole, ( 1.48) Terbinafm, (1.49) Tetraconazole, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Tridemorph, (1.53) Triflumizole, (1.54) Triforin, (1.55) Triticonazole, (1.56) Uniconazole, (1.57) Uniconazole-p , (1.58) viniconazole, (1.59) voriconazole, (1.60) 1- (4-chlorophenyl) -2- (1H-l, 2,4-triazol-1-yl) cycloheptanol, (1.61) methyl-1 - (2 , 2-dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imidazole-5-carboxylate, (1.62) N '- {5- (difluoromethyl) -2-methyl-4- [ 3- (trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, (1.63) N -ethyl-N-methyl-N'-2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl ) propoxy] phenyl} imidoformamide and (1.64) 0- [1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl] -1H-imidazole-1-carbothioate, (1.65) pyrisoxazoles. (2) inhibitors of respiration (respiratory chain inhibitors) such as (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, ( 2.8) Fluxapyroxad, (2.9) Furametpyr, (2.10) Furmecyclox, (2.11) Isopyrazam Mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empimidal racemate 1RS, 4SR, 9SR, (2.12) isopyrazam (anti- epimeric racemate ), (2.13) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.14) isopyrazam (anti- epimeric enantiomer 1S, 4R, 9R), (2.15) isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxine, (2.20) penflufen, (2.21) Penthiopyrad, (2.22) Sedaxanes, (2.23) Thifluzamide, (2.24) 1-Methyl-N- [2- (1, 1, 2,2-tetrafluoroethoxy) phenyl] -3- (trifluoromethyl) -1 H -pyrazole-4 - carboxamide, (2.25) 3- (difluoromethyl) -1-methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] -1 H -pyrazole ol-4-carboxamide, (2.26) 3 - (difluoromethyl) -N- [4-fluoro-2- (1,1,3,3,3,3-hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazole -4-carboxamide, (2.27) N- [1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (2.28 ) 5,8-Difluoro-N- [2- (2-fluoro-4 - {[4- (trifluoromethyl) pyridin-2-yl] oxy} phenyl) ethyl] quinazolin-4-amine, (2.29) benzovindiflupyr, ( 2.30) N - [(IS, 4R) -9- (dichloromethylene) -1,3,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl) -l-methyl-1H- pyrazole-4-carboxamide and (2.31) N- [(1R, 4S) -9- (dichloromethylene) -1,2,3,4-tetrahydro-1,4-methanonaphthalene-5-yl] -3- (difluoromethyl ) - 1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3 - (difluoromethyl) -1-methyl-N- (1,1,3-trimethyl-2,3-dihydro-1H- inden-4-yl) -1H-pyrazole-4-carboxamide, (2.33) 1, 3,5-trimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl ) -LH-pyrazole-4-carboxamide, (2.34) 1-methyl-3- (trifluoromethyl) -N- (1, 1, 3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1 H-pyrazole-4-carboxamide, (2.35) 1-methyl-3 - (trifluoromethyl) -N- [(3R) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1H-pyrazole-4-carboxamide, (2.36) 1-methyl-3- (trifluoromethyl) -N - [(3S) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl ] -LH-pyrazole-4-carboxamide, (2.37) 3- (difluoromethyl) -l-methyl-N - [(3S) -l, l, 3-trimethyl-2,3-dihydro-1H-indene-4 yl] -1H-pyrazole-4-carboxamide, (2.38) 3- (difluoromethyl) -1-methyl-N- [(3R) -1,3,3-trimethyl-2,3-dihydro-1H-indene 4-yl] -1 H -pyrazole-4-carboxamide, (2.39) 1, 3,5-trimethyl-N- [(3R) -1,3,3-trimethyl-2,3-dihydro-1H-indene 4-yl] - 1H-pyrazole-4-carboxamide, (2.40) 1, 3,5-trimethyl-N- [(3S) -1,1,3-trimethyl-2,3-dihydro-1H inden-4-yl] -LH-pyrazole-4-carboxamide, (2.41) benodanil, (2.42) 2-chloro-N- (1, l, 3-trimethyl-2,3-dihydro-1H- inden-4-yl) pyridine-3-carboxamide, (2.43) isofetamide
(3) Inhibitoren der Respiration (Atmungsketten-Inhibitoren) am Komplex III der Atumungskette, wie beispielsweise (3.1) Ametoctradin, (3.2) Amisulbrom, (3.3) Azoxystrobin, (3.4) Cyazofamid, (3.5) Coumethoxystrobin, (3.6) Coumoxystrobin, (3.5) Dimoxystrobin, (3.8) Enestroburin, (3.9) Famoxadon, (3.10) Fenamidon, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-Methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2- {[6-(3-Chlor-2-methylphenoxy)-5-fluorpyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N- methylethanamid, (3.24) (2E)-2-(Methoxyimino)-N-methyl-2-(2- { [( {( 1 E)- 1 - [3 -(3) inhibitors of respiration (respiratory chain inhibitors) at the complex III of the respiratory chain, such as (3.1) ametoctradine, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamide, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, ( 3.5) dimoxystrobin, (3.8) enestroburine, (3.9) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) kresoxime-methyl, (3.14) metominostrobin, (3.15) orysastrobin, (3.16) picoxystrobin , (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, (3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E) -2- (2- {[6- (3- Chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylethanamide, (3.24) (2E) -2- (methoxyimino) -N-methyl-2- ( 2- {[({(1 E) - 1 - [3 -
(trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)ethanamid, (3.25) (2E)-2-(Methoxyimino)-N- methyl-2- {2- [(E)-( { 1 - [3 -(trifluormethyl)phenyl]ethoxy} imino)methyl]phenyl} ethanamid, (3.26) (2E)-2- {2- [({[(lE)-l-(3- {[(E)-l-Fluor-2-phenylethenyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylethanamid, (3.27) (2E)-2- {2- [( { [(2E,3E)-4-(2,6-Dichlorphenyl)but-3 -en-2- ylidenjamino } oxy)methyl]phenyl} -2-(methoxyimino)-N-methylethanamid, (3.28) 2-Chlor-N-( 1 ,1,3- trimethyl-2,3 -dihydro- 1 H-inden-4-yl)pyridin-3 -carboxamid, (3.29) 5-Methoxy-2-methyl-4-(2- { [( {( 1 E)- 1 - [3-(trifluormethyl)phenyl]ethyliden}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-l,2,4-triazol-3-on, (3.30) Methyl-(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3- methoxyprop-2-enoat, (3.31) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamid, (3.32) 2- {2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (4) Inhibitoren der Mitose und Zellteilung, wie beispielsweise (4.1) Benomyl, (4.2) Carbendazim, (4.3) Chlorfenazol, (4.4) Diethofencarb, (4.5) Ethaboxam, (4.6) Fluopicolid, (4.7) Fuberidazol, (4.8) Pencycuron, (4.9) Thiabendazol, (4.10) Thiophanat-Methyl, (4.11) Thiophanat, (4.12) Zoxamid, (4.13) 5-Chlor-7-(4-methylpiperidin-l-yl)-6- (2,4,6-trifluorphenyl)[l,2,4]triazolo[l,5-a]pyrimidin und (4.14) 3-Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4- (2,4,6-trifluorphenyl)pyridazin. (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) ethanamide, (3.25) (2E) -2- (methoxyimino) -N-methyl-2- {2- [(E) - ({1 - [3 - (trifluoromethyl) phenyl] ethoxy} imino) methyl] phenyl} ethanamide, (3.26) (2E) -2- {2- [({[(IE) -l- (3- {[(E) -l-fluoro -2-phenylethenyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethanamide, (3.27) (2E) -2- {2- [({[(2E, 3E ) -4- (2,6-dichlorophenyl) but-3 -en-2-ylidenemino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethaneamide, (3.28) 2-chloro-N- (1, 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, (3.29) 5-methoxy-2-methyl-4- (2- {[({(1 E ) - 1 - [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-l, 2,4-triazol-3-one, (3.30) methyl (2E ) -2- {2 - [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyprop-2-enoate, (3.31) N- (3-ethyl-3,5, 5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide, (3.32) 2- {2 - [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide, (4) inhibit mitosis and cell division, such as (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5) ethaboxam, (4.6) fluopicolide, (4.7) fuberidazole, (4.8) pencycuron, (4.9 ) Thiabendazole, (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [l, 2,4] triazolo [l, 5-a] pyrimidine and (4.14) 3-Chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl ) pyridazine.
(5) Verbindungen mit Multisite-Aktivität, wie beispielsweise (5.1) Bordeauxmischung, (5.2) Captafol, (5.3) Captan, (5.4) Chlorthalonil, (5.5) Kupferzubereitungen wie Kupferhydroxid, (5.6) Kupfernaphthenat, (5.7) Kupferoxid, (5.8) Kupferoxychlorid, (5.9) Kupfersulfat, (5.10) Dichlofluanid, (5.11) Dithianon, (5.12) Dodine, (5.13) Dodine freie Base, (5.14) Ferbam, (5.15) Fluorfolpet, (5.16) Folpet, (5.17) Guazatin, (5.18) Guazatinacetat, (5.19) Iminoctadin, (5.20) Iminoctadinalbesilat, (5.21) Iminoctadintriacetat, (5.22) Mankupfer, (5.23) Mancozeb, (5.24) Maneb, (5.25) Metiram, (5.26) Zinkmetiram, (5.27) Kupfer-Oxin, (5.28) Propamidin, (5.29) Propineb, (5.30) Schwefel und Schwefelzubereitungen wie beispielsweise Calciumpolysulfid, (5.31) Thiram, (5.32) Tolylfluanid, (5.33) Zineb, (5.34) Ziram und (5,35) Anilazin. (5) Compounds with multisite activity, such as (5.1) Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5) copper compounds such as copper hydroxide, (5.6) copper naphthenate, (5.7) copper oxide, (5.8 ) Copper oxychloride, (5.9) copper sulfate, (5.10) dichlorofluanide, (5.11) dithianon, (5.12) Dodine, (5.13) dodine free base, (5.14) ferbam, (5.15) fluoro folpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) iminoctadinalesilate, (5.21) iminoctadine triacetate, ( 5.22) Man copper, (5.23) mancozeb, (5.24) maneb, (5.25) metiram, (5.26) zinc metiram, (5.27) copper oxine, (5.28) propamidine, (5.29) propylene, (5.30) sulfur and sulfur compounds such as calcium polysulfide , (5.31) thiram, (5.32) tolylfluanid, (5.33) zineb, (5.34) ziram, and (5.35) anilazine.
(6) Resistenzinduktoren, wie beispielsweise (6.1) Acibenzolar-S-Methyl, (6.2) Isotianil, (6.3) Probenazol, (6.4) Tiadinil und (6.5) Laminarin. (6) resistance inducers such as (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) tiadinil, and (6.5) laminarin.
(7) Inhibitoren der Aminosäure- und Protein-Biosynthese, wie beispielsweise (7.1) , (7.2) Blasticidin-S, (7.3) Cyprodinil, (7.4) Kasugamycin, (7.5) Kasugamycin Hydrochlorid Hydrat, (7.6) Mepanipyrim, (7.7) Pyrimethanil, (7.8) 3-(5-Fluor-3,3,4,4-tetramethyl-3,4-dihydroisochinolin-l-yl)chinolin und (7.9) Oxytetracyclin und (7.10) Streptomycin. (7) inhibitors of amino acid and protein biosynthesis, such as (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) Pyrimethanil, (7.8) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl) quinoline and (7.9) oxytetracycline and (7.10) streptomycin.
(8) Inhibitoren der ATP Produktion, wie beispielsweise (8.1) Fentin Acetat, (8.2) Fentin Chlorid, (8.3) Fentin Hydroxid und (8.4) Silthiofam. (8) inhibitors of ATP production, such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) silthiofam.
(9) Inhibitoren der Zellwandsynthese, wie beispielsweise (9.1) Benthiavalicarb, (9.2) Dimethomorph, (9.3) Flumorph, (9.4) Iprovalicarb, (9.5) Mandipropamid, (9.6) Polyoxins, (9.7) Polyoxorim, (9.8) Validamycin(9) inhibitors of cell wall synthesis, such as (9.1) benthi- avalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamide, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin
A, (9.9) Valifenalat und (9.10) Polyoxin B. A, (9.9) Valifenalate and (9.10) Polyoxin B.
(10) Inhibitoren der Lipid- und Membran-Synthese, wie beispielsweise (10.1) Biphenyl, (10.2) Chlorneb, (10.3) Dicloran, (10.4) Edifenphos, (10.5) Etridiazol, (10.6) Iodocarb, (10.7) Iprobenfos, (10.8) Isoprothiolan, (10.9) Propamocarb, (10.10) Propamocarb Hydrochlorid, (10.11) Prothiocarb,, (10.12) Pyrazophos, (10.13) Quintozen, (10.14) Tecnazene und (10.15) Tolclofos-Methyl. (10) inhibitors of lipid and membrane synthesis, such as (10.1) biphenyl, (10.2) chloroben, (10.3) diclorane, (10.4) edifenphos, (10.5) etridiazole, (10.6) iodocarb, (10.7) Iprobenfos, ( 10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb ,, (10.12) pyrazophos, (10.13) quintoene, (10.14) tecnazene and (10.15) tolclofos-methyl.
(11) Inhibitoren der Melanin-Biosynthese, wie beispielsweise (11.1) Carpropamid, (11.2) Diclocymet, (11.3) Fenoxanil, (11.4) Fthalid, (11.5) Pyroquilon, (11.6) Tricyclazol, und (11.7) 2,2,2-Trifluorethyl {3- methyl- 1 - [(4-methylbenzoyl)amino]butan-2-yl} carbamat. (11) inhibitors of melanin biosynthesis, such as (11.1) carpropamide, (11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilone, (11.6) tricyclazole, and (11.7) 2,2,2 Trifluoroethyl {3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl} carbamate.
(12) Inhibitoren der Nukleinsäuresynthese, wie beispielsweise (12.1) Benalaxyl, (12.2) Benalaxyl-M (Kiralaxyl), (12.3) Bupirimat, (12.4) Clozylacon, (12.5) Dimethirimol, (12.6) Ethirimol, (12.7) Furalaxyl,(12) inhibitors of nucleic acid synthesis such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furalaxyl,
(12.8) Hymexazol, (12.9) Metalaxyl, (12.10) Metalaxyl-M (Mefenoxam), (12.11) Ofurace, (12.12) Oxadixyl, (12.13) Oxolinsäure und (12.14) Octhilinon. (12.8) hymexazole, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11) ofurace, (12.12) oxadixyl, (12.13) oxolinic acid and (12.14) octhilinone.
(13) Inhibitoren der Signaltransduktion, wie beispielsweise (13.1) Chlozolinat, (13.2) Fenpiclonil, (13.3) Fludioxonil, (13.4) Iprodion, (13.5) Procymidon, (13.6) Quinoxyfen, (13.7) Vinclozolin und (13.8) Proquinazid. (14) Entkoppler, wie beispielsweise (14.1) Binapacryl, (14.2) Dinocap, (14.3) Ferimzon, (14.4) Fluazinam und (14.5) Meptyldinocap. (13) Signal transduction inhibitors such as (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione, (13.5) procymidone, (13.6) quinoxyfen, (13.7) vinclozoline, and (13.8) proquinazide. (14) decouplers such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam, and (14.5) meptyldinocap.
(15) Weitere Verbindungen, wie beispielsweise (15.1) Benthiazol, (15.2) Bethoxazin, (15.3) Capsimycin, (15.4) Carvon, (15.5) Chinomethionat, (15.6) Pyriofenon (Chlazafenon), (15.7) Cufraneb, (15.8) Cyflufenamid, (15.9) Cymoxanil, (15.10) Cyprosulfamid, (15.11) Dazomet, (15.12) Debacarb, (15.13) Dichlorphen, (15.14) Diclomezin, (15.15) Difenzoquat, (15.16) Difenzoquat Methylsulphat, (15.17) Diphenylamin, (15.18) Ecomat, (15.19) Fenpyrazamin, (15.20) Flumetover, (15.21) Fluorimid, (15.22) Flusulfamid, (15.23) Flutianil, (15.24) Fosetyl-Aluminium, (15.25) Fosetyl-Calcium, (15.26) Fosetyl- Natrium, (15.27) Hexachlorbenzol, (15.28) Irumamycin, (15.29) Methasulfocarb, (15.30) Methylisothiocyanat, (15.31) Metrafenon, (15.32) Mildiomycin, (15.33) Natamycin, (15.34) Nickel Dimethyldithiocarbamat, (15.35) Nitrothal-Isopropyl, (15.36) Octhilinone, (15.37) Oxamocarb, (15.38) Oxyfenthiin, (15.39) Pentachlorphenol und dessen Salze, (15.40) Phenothrin, (15.41) Phosphorsäure und deren Salze, (15.42) Propamocarb-Fosetylat, (15.43) Propanosin-Natrium, (15.44) Pyrimorph, (15.45) (2E)- 3-(4-Tert-butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on, (15.46) (2Z)-3-(4-Tert- butylphenyl)-3-(2-chlorpyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-on, (15.47) Pyrrolnitrin, (15.48) Tebufloquin, (15.49) Tecloftalam, (15.50) Tolnifanide, (15.51) Triazoxid, (15.52) Trichlamid, (15.53) Zarilamid, (15.54) (3S,6S,7R,8R)-8-Benzyl-3-[( {3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl} carbonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl 2-methylpropanoat, (15.55) 1 -(4- {4-[(5R)-5- (2,6-Difluorphenyl)-4,5-dihydro- 1 ,2-oxazol-3-yl] - 1 ,3 -thiazol-2-yl} piperidin- 1 -yl)-2- [5-methyl-3 - (trifluormethyl)- lH-pyrazol- 1 -yl]ethanon, (15.56) 1 -(4- {4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-l ,2- oxazol-3 -yl] - 1 ,3 -thiazol-2-yl}piperidin- 1 -yl)-2- [5-methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1 -yl] ethanon, (15.57) l-(4-{4-[5-(2,6-Difluoφhenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5 methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1-yl] ethanon, (15.58) l-(4-Methoxyphenoxy)-3,3-dimethylbutan-2-yl lH-imidazole-l-carboxylat, (15.59) 2,3,5,6-Tetrachlor-4-(methylsulfonyl)pyridin, (15.60) 2,3-Dibutyl-6- chlorthieno[2,3-d]pyrimidin-4(3H)-on, (15.61) 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole- l,3,5,7(2H,6H)-tetron, (15.62) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l-(4-{4-[(5R)-5-phenyl- 4,5-dihydro- 1 ,2-oxazol-3 -yl] - 1 ,3 -thiazol-2-yl} piperidin- 1 -yl)ethanon, ( 15.63) 2- [5-Methyl-3 -(15) Other compounds such as (15.1) benthiazole, (15.2) bethoxazine, (15.3) capsimycin, (15.4) carvone, (15.5) quinomethionate, (15.6) pyriofenone (Chlazafenone), (15.7) Cufraneb, (15.8) cyflufenamid , (15.10) Cymoxanil, (15.10) Cyprosulfamide, (15.11) Dazomet, (15.12) Debacarb, (15.13) Dichlorophene, (15.14) Diclomethine, (15.15) Difenzoquat, (15.16) Difenzoquat Methylsulphate, (15.17) Diphenylamine, (15.18) Ecomat, (15.19) Fenpyrazamine, (15.20) Flumetover, (15.21) Fluorimide, (15.22) Flusulfamide, (15.23) Flutianil, (15.24) Fosetyl-aluminum, (15.25) Fosetyl-calcium, (15.26) Fosetyl-sodium, (15.27 ) Hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb, (15.30) methylisothiocyanate, (15.31) metrafenone, (15.32) mildiomycin, (15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35) nitrothal-isopropyl, (15.36) octhilinones , (15.37) Oxamocarb, (15.38) Oxyfenthiine, (15.39) Pentachlorophenol and its salts, (15.40) Phenothrin, (15.41) Phosphoric acid and its salts, (15.42) Propamocarb-fosetylate, (15.43) propanosine sodium, (15.44) pyrimorph, (15.45) (2E) - 3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine) 4-yl) prop-2-en-1-one, (15.46) (2Z) -3- (4-tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholine-4 yl) prop-2-en-1-one, (15.47) pyrrolynitrin, (15.48) tebufloquine, (15.49) tecloftalam, (15.50) tolnifanide, (15.51) triazoxide, (15.52) trichlamide, (15.53) zarilamide, (15.54) (3S, 6S, 7R, 8R) -8-Benzyl-3 - [({3 - [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo - 1, 5-dioxonan-7-yl 2-methylpropanoate, (15.55) 1 - (4- {4 - [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1, 2- oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3 - (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (15.56) 1 - (4- {4 - [(5S) -5- (2,6-Difluorophenyl) -4,5-dihydro-1, 2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidine-1-yl) -2- [5-methyl-3 - (trifluoromethyl) -1-H-pyrazol-1-yl] ethanone, (15.57) 1- (4- {4- [5- (2,6-) Difluoφhenyl) -4,5-dihydro-l, 2-oxazol-3-yl] -l, 3-thi azol-2-yl} piperidin-1-yl) -2- [5-methyl-3 - (trifluoromethyl) -1-H-pyrazol-1-yl] ethanone, (15.58) 1- (4-methoxyphenoxy) -3.3 -dimethylbutan-2-yl 1H-imidazole-1-carboxylate, (15.59) 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, (15.60) 2,3-dibutyl-6-chlorothieno [2,3 -d] pyrimidin-4 (3H) -one, (15.61) 2,6-dimethyl-1H, 5H- [l, 4] dithiino [2,3-c: 5,6-c '] dipyrrole I, 3 , 5,7 (2H, 6H) -tetron, (15.62) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4 - [(5R) - 5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, (15.63) 2- [5-methyl-3 -
(trifluormethyl)-lH-pyrazol-l-yl]-l-(4- {4-[(5S)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2- yl}piperidin-l-yl)ethanon, (15.64) 2-[5-Methyl-3-(trifluormethyl)-lH-pyrazol-l-yl]-l- {4-[4-(5-phenyl-4,5- dihydro- 1 ,2-oxazol-3 -yl)- 1 ,3 -thiazol-2-yl]piperidin- 1 -yl} ethanon, (15.65) 2-Butoxy-6-iodo-3-propyl-4H- chromen-4-οη, (15.66) 2-Chlor-5-[2-chlor-l-(2,6-difluor-4-methoxyphenyl)-4-methyl-lH-imidazol-5- yl]pyridin, (15.67) 2-Phenylphenol und Salze, (15.68) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4- dihydroisochinolin-l-yl)chinolin, (15.69) 3,4,5-Trichlorpyridine-2,6-dicarbonitril, (15.70) 3-Chlor-5-(4- chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (15.71) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)- 3,6-dimethylpyridazin, (15.72) 5-Amino-l,3,4-thiadiazole-2-thiol, (15.73) 5-Chlor-N'-phenyl-N'-(prop-2- yn-l-yl)thiophene-2-sulfonohydrazid, (15.74) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.75) 5- Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.76) 5-Methyl-6-octyl[l,2,4]triazolo[l,5-a]pyrimidin- 7-amin, (15.77) Ethyl (2Z)-3-amino-2-cyano-3-phenylacrylat, (15.78) N'-(4- {[3-(4-Chlorbenzyl)-l,2,4- thiadiazol-5-yl]oxy} -2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (15.79) N-(4-Chlorbenzyl)-3- [3 -methoxy-4-(prop-2-yn- 1 -yloxy)phenyl]propanamid, (15.80) N-[(4-Chlorphenyl)(cyano)methyl] -3 - [3 - methoxy-4-(prop-2-yn- 1 -yloxy)phenyl]propanamid, (15.81) N- [(5-Brom-3 -chlorpyridin-2-yl)methyl] -2,4- dichlornicotinamid, (15.82) N-[l-(5-Brom-3-chloφyridin-2-yl)ethyl]-2,4-dichlornicotinamid, (15.83) N-[l- (5-Brom-3-chloφyridin-2-yl)ethyl]-2-fluor-4-iodonicotinamid, (15.84) N-{(E)-(trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4 - [(5S) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1, 3 -thiazol-2-yl} piperidin-1-yl) ethanone, (15.64) 2- [5-Methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- [4- [4- (5 -phenyl-4,5-dihydro-1,2-oxazol-3-yl) -1,3-thiazol-2-yl] piperidin-1-yl} ethanone, (15.65) 2-butoxy-6-iodo-3 -propyl-4H-chromen-4-one, (15.66) 2-Chloro-5- [2-chloro-L- (2,6-difluoro-4-methoxyphenyl) -4-methyl-1H-imidazol-5-yl ] pyridine, (15.67) 2-phenylphenol and salts, (15.68) 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (15.69) 3,4 , 5-Trichloropyridine-2,6-dicarbonitrile, (15.70) 3-Chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl) -6-methylpyridazine, (15.71) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, (15.72) 5-amino-l, 3,4-thiadiazole-2-thiol, (15.73) 5-chloro-N'-phenyl-N ' - (prop-2-yn-1-yl) thiophene-2-sulfonohydrazide, (15.74) 5-fluoro-2 - [(4-fluorobenzyl) oxy] pyrimidin-4-amine, (15.75) 5- Fluoro-2 - [(4-methylbenzyl) oxy] pyrimidin-4-amine, (15.76) 5-methyl-6-octyl [l, 2,4] triazolo [l, 5-a] pyrimidine-7-amine, ( 15.77) Ethyl (2Z) -3-amino-2-cyano-3-phenylacrylate, (15.78) N '- (4- {[3- (4-chlorobenzyl) -1,2,4-thiadiazol-5-yl] oxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (15.79) N- (4-chlorobenzyl) -3- [3-methoxy-4- (prop-2-yn-1-yloxy) phenyl ] propanamide, (15.80) N - [(4-Chlorophenyl) (cyano) methyl] -3 - [3-methoxy-4- (prop-2-yn-1-yloxy) phenyl] propanamide, (15.81) N- [ (5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloronotinamide, (15.82) N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2,4- Dichloromicotinamide, (15.83) N- [1- (5-Bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodonicotinamide, (15.84) N - {(E) -
[(Cyclopropylmethoxy)imino][6-(difluormethox (15.85) N-{(Z)-[(Cyclopropylmethoxy)imino][6-(difluorm [(Cyclopropylmethoxy) imino] [6- (difluoromethoxy (15.85) N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethane
(15.86) N'-{4-[(3-Tert-bu1yl-4-cyano-l,2-thiazol-5-yl)oxy]-2-chlor-5-methylphenyl}-N-e methylimidoformamid, (15.87) N-Methyl-2-(l- {[5-methyl-3-(trifluormethyl)-lH-pyrazol-l- yl] acetyl} piperidin-4-yl)-N-( 1 ,2,3,4-tetrahydronaphthalen- 1 -yl)-l ,3 -thiazole-4-carboxamid, (15.88) N- Methyl-2-(l - { [5-methyl-3 -(trifluormethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N-[(lR)-l,2,3,4- tetrahydronaphthalen-l-yl]-l,3-thiazole-4-carboxamid, (15.89) N-Methyl-2-(l- {[5-methyl-3- (trifluormethyl)- 1 H-pyrazol- 1 -yl] acetyl} piperidin-4-yl)-N- [(1S)-1 ,2,3,4-tetrahydronaphthalen- 1 -yl]- 1 ,3- thiazole-4-carboxamid, (15.90) Pentyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl]pyridin-2-yl } carbamat, (15.91) Phenazine- 1 -carbonsäure, (15.92) Chinolin-8-ol, (15.93) Chinolin-8-ol sulfate (2:1), (15.94) Tert-butyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.95) l-Methyl-3-(trifluormethyl)-N- [2'-(trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (15.96) N-(4'-Chlorbiphenyl-2-yl)-3- (difluormethyl)-l -methyl- 1 H-pyrazol-4-carboxamid, (15.97) N-(2',4'-Dichlorbiphenyl-2-yl)-3-(15.86) N '- {4 - [(3-tert-butyl-4-cyano-1,2-thiazol-5-yl) oxy] -2-chloro-5-methylphenyl} -N-methylimidoformamide, (15.87) N -Methyl 2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -acetyl} piperidin-4-yl) -N- (1,2,3,4-tetrahydronaphthalene) 1 -yl) -1,3-thiazole-4-carboxamide, (15.88) N-methyl-2- (1 - {[5-methyl-3 - (trifluoromethyl) -1 H -pyrazol-1-yl] acetyl} piperidin-4-yl) -N - [(1R) -l, 2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazole-4-carboxamide, (15.89) N -methyl-2- (1 - {[5-methyl-3- (trifluoromethyl) -1 H -pyrazol-1-yl] -acetyl} -piperidin-4-yl) -N- [(1S) -1, 2,3,4-tetrahydronaphthalene-1 - yl] - 1, 3-thiazole-4-carboxamide, (15.90) pentyl {6 - [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridine 2-yl} carbamate, (15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol, (15.93) quinoline-8-ol sulfate (2: 1), (15.94) tert-butyl {6 - [( {[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.95) 1-methyl-3- (trifluoromethyl) -N- [ 2 '- (trifluormeth yl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (15.96) N- (4'-chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4 carboxamide, (15.97) N- (2 ', 4'-dichlorobiphenyl-2-yl) -3-
(difluormethyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.98) 3 -(Difluormethyl)- 1 -methyl-N- [4 - (trifluormethyl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (15.99) N-(2',5'-Difluorbiphenyl-2-yl)-l-methyl- 3-(trifluormethyl)-lH-pyrazol-4-carboxamid, (15.100) 3-(Difluormethyl)-l-methyl-N-[4'-(prop-l-yn-l- yl)biphenyl-2-yl]-lH-pyrazol-4-carboxamid, (15.101) 5-Fluor-l,3-dimethyl-N-[4'-(prop-l-yn-l- yl)biphenyl-2-yl] - 1 H-pyrazol-4-carboxamid, ( 15.102) 2-Chlor-N-[4'-(prop- 1 -yn- 1 -yl)biphenyl-2- yl]nicotinamid, ( 15.103) 3 -(Difluormethyl)-N-[4'-(3,3-dimethylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 -methyl- 1 H- pyrazol-4-carboxamid, (15.104) N-[4'-(3,3-dimethylbut- 1 -yn-1 -yl)biphenyl-2-yl]-5-fluor- 1 ,3-dimethyl- 1 H- pyrazol-4-carboxamid, ( 15.105) 3 -(Difluormethyl)-N-(4'-ethynylbiphenyl-2-yl)- 1 -methyl- 1 H-pyrazol-4- carboxamid, (15.106) N-(4'-Ethynylbiphenyl-2-yl)-5-fluor-l,3-dimethyl-lH-pyrazol-4-carboxamid, (15.107) 2-Chlor-N-(4'-ethynylbiphenyl-2-yl)nicotinamid, (15.108) 2-Chlor-N-[4'-(3,3-dimethylbut- 1 -yn- 1 - yl)biphenyl-2-yl]nicotinamid, ( 15.109) 4-(Difluormethyl)-2-methyl-N- [4'-(trifluormethyl)biphenyl-2-yl] - l,3-thiazole-5-carboxamid, (15.110) 5-Fluor-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l,3- dimethyl-lH-pyrazol-4-carboxamid, (15.111) 2-Chlor-N-[4'-(3-hydroxy-3-methylbut-l-yn-l-yl)biphenyl-2- yl]nicotinamid, (15.112) 3-(Difluormethyl)-N-[4'-(3-methoxy-3-methylbut-l-yn-l-yl)biphenyl-2-yl]-l- methyl- 1 H-pyrazol-4-carboxamid, (15.113) 5-Fluor-N- [4'-(3 -methoxy-3-methylbut- 1 -yn- 1 -yl)biphenyl-2- yl] - 1 ,3-dimethyl- 1 H-pyrazol-4-carboxamid, (15.114) 2-Chlor-N- [4 '-(3 -methoxy-3-methylbut- 1 -yn- 1 - yl)biphenyl-2-yl]nicotinamid, (15.115) (5-Brom-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6- methylphenyl)methanon, (15.116) N- [2-(4- { [3-(4-Chloφhenyl)prop-2-yn- 1 -yl] oxy} -3 - methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamid, (15.117) 4-Oxo-4-[(2-phenylethyl)amino]butansäure, (15.118) But-3-yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.119) 4-Amino-5-fluorpyrimidin-2-ol (Tautomere Form: 4-Amino-5-fluorpyrimidin-2(lH)-on), (15.120) Propyl 3,4,5-trihydroxybenzoat, (15.121) 1 ,3-Dimethyl-N-(l , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl)- 1 H-pyrazol-4-carboxamid, ( 15.122) 1,3- Dimethyl-N-[(3R)-l,l,3-trimethyl-2,3-dih^^ (15.123) 1,3-(difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.98) 3 - (difluoromethyl) -1-methyl-N- [4 - (trifluoromethyl) biphenyl-2-yl] -1H-pyrazole-4 -carboxamide, (15.99) N- (2 ', 5'-Difluorobiphenyl-2-yl) -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide, (15.100) 3- (difluoromethyl) -1 -methyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -1H-pyrazole-4-carboxamide, (15.101) 5-fluoro-1,3-dimethyl-N- [4 '- (prop-1-yn-1-yl) biphenyl-2-yl] -1-H-pyrazole-4-carboxamide, (15.102) 2-chloro-N- [4' - (prop-1-yn 1 -yl) biphenyl-2-yl] nicotinamide, (15.103) 3- (difluoromethyl) -N- [4 '- (3,3-dimethylbut-1 -yn-1-yl) biphenyl-2-yl] - 1-methyl-1H-pyrazole-4-carboxamide, (15.104) N- [4 '- (3,3-dimethylbut-1 -yn-1-yl) biphenyl-2-yl] -5-fluoro-1, 3-dimethyl-1H-pyrazole-4-carboxamide, (15.105) 3- (difluoromethyl) -N- (4'-ethynyl-biphenyl-2-yl) -1-methyl-1H-pyrazole-4-carboxamide, (15.106 ) N- (4'-Ethynyl-biphenyl-2-yl) -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.107) 2-chloro-N- (4'-ethynyl-biphenyl-2-yl ) nicotinamide, (15.108) 2-Chloro -N- [4 '- (3,3-dimethylbut-1 -yn-1-yl) biphenyl-2-yl] nicotinamide, (15.109) 4- (difluoromethyl) -2-methyl-N- [4' - ( trifluoromethyl) biphenyl-2-yl] -1,3-thiazole-5-carboxamide, (15,110) 5-fluoro-N- [4 '- (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl 2-yl] -1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.111) 2-Chloro-N- [4 '- (3-hydroxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] nicotinamide, (15.112) 3- (difluoromethyl) -N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -l-methyl 1-H-pyrazole-4-carboxamide, (15.113) 5-fluoro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1-yl) biphenyl-2-yl] -1,3 -dimethyl-1H-pyrazole-4-carboxamide, (15.114) 2-chloro-N- [4 '- (3-methoxy-3-methylbut-1-yn-1 - yl) biphenyl-2-yl] nicotinamide, (15.115) (5-bromo-2-methoxy-4-methylpyridin-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (15.116) N- [2- (4- {[3- (4-Chloro-phenyl) -prop-2-yn-1-yl] oxy-3-methoxyphenyl) -ethyl] -N2- (methylsulfonyl) -valinamide, (15.117) 4-oxo-4 - [(2-phenylethyl) amino] butanoic acid, (15,118) but-3-yn-1-yl {6 - [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} carbamate, (15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidine-2 (1H) -one), (15,120) Propyl 3,4,5-trihydroxybenzoate, (15,121) 1, 3-Dimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1H pyrazole-4-carboxamide, (15.122) 1,3-dimethyl-N - [(3R) -l, l, 3-trimethyl-2,3-dih ^^ (15,123) 1,3-
Dimethyl-N-[(3 S)- 1 , 1 ,3 -trimethyl-2,3 -dihydro- 1 H-inden-4-yl] - 1 H-pyrazol-4-carboxamid, ( 15.124) [3 -(4- CWor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.125) (S)-[3-(4- Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.126) (R)-[3-(4- Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-l,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.127) 2- {[3-(2- Chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H- 1 ,2,4-triazol-3 -thion, (15.128) 1 - { [3 -(2-Chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol-5-yl thiocyanat, (15.129) 5- (Allylsulfanyl)- 1 - { [3-(2-chlorphenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol, (15.130) 2-[l-(2,4-Dichloφhenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, ( 15.131 ) 2- { [rel(2R,3 S)-3-(2-Chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} -2,4-dihydro-3H- 1 ,2,4- triazol-3-thion, (15.132) 2- {[rel(2R,3R)-3-(2-Chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl}-2,4- dihydro-3H-l,2,4-triazol-3-thion, (15.133) l-{[rel(2R,3S)-3-(2-Chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2- yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanat, (15.134) l- {[rel(2R,3R)-3-(2-Ch^henyl)-2-(2,4- difluoφhenyl)oxiran-2-yl]methyl}-lH-l,2,4-triazol-5-yl thiocyanat, (15.135) 5 -(Allylsulfanyl)- 1- { [rel(2R,3 S)-3 -(2-chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4-triazol, (15.136) 5- (Allylsulfanyl)- 1 - { [rel(2R,3R)-3-(2-chloφhenyl)-2-(2,4-difluoφhenyl)oxiran-2-yl]methyl} - 1 H- 1 ,2,4- triazol, (15.137) 2-[(2S,4S,5S)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro- 3H- 1 ,2,4-triazol-3 -thion, ( 15.138) 2- [(2R,4S,5S)- 1 -(2,4-Dichloφhenyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (15.139) 2-[(2R,4R,5R)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6- trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3 -thion, ( 15.140) 2- [(2S,4R,5R)- 1 -(2,4-Dich^henyl)- 5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (15.141) 2-[(2S,4S,5R)-l-(2,4- Dichloφhenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-l,2,4-triazol-3-thion, (15.142) 2- [(2R,4S,5R)- 1 -(2,4-Dichloφhenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3 - thion, (15.143) 2-[(2R,4R,5S)-l-(2,4-Dichloφhenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro- 3H-l,2,4-triazol-3 -thion, (15.144) 2-[(2S,4R,5S)-l-(2,4-Dich^henyl)-5-hydroxy-2,6,6-trimethylheptan-4- yl] -2,4-dihydro-3H- 1 ,2,4-triazol-3-thion, ( 15.145) 2-Fluor-6-(trifluormethyl)-N-( 1 , 1 ,3-trimethyl-2,3- dihydro-lH-inden-4-yl)benzamid, (15.146) 2-(6-Benzylpyridin-2-yl)quinazolin, (15.147) 2-[6-(3-Fluor-4- methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.148) 3-(4,4-Difluor-3,3-dimethyl-3,4- dihydroisochinolin-l-yl)chinolin, (15.149) Abscisinsäure, (15.150) 3-(Difluormethyl)-N-methoxy-l- methyl-N- [1 -(2,4,6-trichloφhenyl)propan-2-yl] - 1 H-pyrazol-4-carboxamid, (15.151) N'- [5-Brom-6-(2,3 - dihydro- 1 H-inden-2-yloxy)-2-methylpyridin-3 -yl] -N-ethyl-N-methylimidoformamid, (15.152) N'- {5-Brom- 6-[l-(3,5-difluo^henyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofo (15.153) N'- {5-Dimethyl-N - [(3S) -1,3,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazole-4-carboxamide, (15.124) [3 - ( 4-C-nor-2-fluorophenyl) -5- (2,4-difluorophenyl) -l, 2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.125) (S) - [3- (4 - chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.126) (R) - [3- (4- Chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) -methanol, (15.127) 2- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.128) 1 - {[3 - (2 -Chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H -1,2,4-triazol-5-yl thiocyanate, (15.129) 5- (allylsulfanyl) -1 - { [3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H-1,2,4-triazole, (15,130) 2- [1- (2,4 -Dichloφhenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (15.131) 2- {[rel. 2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3 thion, (15.132) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-l, 2,4 -triazole-3-thione, (15.133) 1 - {[rel (2R, 3S) -3- (2-chloro-phenyl) -2- (2,4-difluoro-phenyl) -oxiran-2-yl] -methyl} -H-1 , 2,4-triazol-5-yl thiocyanate, (15.134) 1- {[rel (2R, 3R) -3- (2-chloro-1-yl) -2- (2,4-difluoro-phenyl) -oxiran-2-yl ] methyl} -LH-l, 2,4-triazol-5-yl thiocyanate, (15.135) 5 - (allylsulfanyl) - 1- {[rel (2R, 3S) -3 - (2-chloro-phenyl) -2-] (2,4-difluorophenyl) oxiran-2-yl] methyl} -1 H-1,2,4-triazole, (15,136) 5- (allylsulfanyl) -1 - {[rel (2R, 3R) -3- ( 2-chloro-phenyl) -2- (2,4-difluoro-phenyl) -oxiran-2-yl] -methyl} -1 H-1,2,4-triazole, (15,137) 2 - [(2S, 4S, 5S) -l- (2,4-dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.138) 2- [(2R, 4S, 5S) -1- (2,4-Dichloro-phenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2, 4-triazole-3-thione, (15,139) 2 - [(2R, 4R, 5R) -1- (2,4-dichloro-5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3-thione, (15.140) 2- [(2S, 4R , 5R) - 1 - (2,4-dichloro) - 5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1, 2,4-triazole-3 -thione, (15,141) 2 - [(2S, 4S, 5R) -1- (2,4-dichloro-phenyl) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro- 3H-l, 2,4-triazole-3-thione, (15.142) 2- [(2R, 4S, 5R) -1- (2,4-Dichloro-phenyl) -5-hydroxy-2,6,6-trimethylheptane 4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (15,143) 2 - [(2R, 4R, 5S) -1- (2,4-dichloro-phenyl) -5 -hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-l, 2,4-triazole-3-thione, (15.144) 2 - [(2S, 4R, 5S) - 1- (2,4-dichloro) -5-hydroxy-2,6,6-trimethylheptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, 15.145) 2-Fluoro-6- (trifluoromethyl) -N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -benzamide, (15.146) 2- (6-Benzyl-pyridine-2 -yl) quinazoline, (15.147) 2- [6- (3-Fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (15,148) 3- (4,4-Difluoro-3,3-dimethyl -3,4-dihydroisoquinolin-1-yl) quinoline, (15,149) abscisic acid, (15,150) 3- (difluoromethyl) -N-methoxy-1-methyl-N- [1- (2,4,6-trichlorophenyl) propane -2 -yl] - 1 H -pyrazole-4-carboxamide, (15.151) N '- [5-bromo-6- (2,3-) dihydro-1H-inden-2-yloxy) -2-methylpyridin-3-yl] -N-ethyl-N-methylimidoformamide, (15.152) N '- {5-bromo-6- [1- (3,5-) difluoroethylenyl) ethoxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidofo (15.153) N'- {5-
Brom-6-[(lR)-l-(3,5-difluo^henyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidof^ Bromo-6 - [(lR) -l- (3,5-difluo ^ henyl) ethoxy] -2-methyl-pyridin-3-yl} -N-ethyl-N-methylimidof ^
(15.154) N'- {5-Brom-6-[(l S)- 1 -(3,5-difluoφhenyl)ethoxy]-2-methylpyridin-3-yl} -N-ethyl-N- methylimidoformamid, (15.155) N'- {5-Brom-6- [(cis-4-isopropylcyclohexyl)oxy] -2-methylpyridin-3 -yl} -N- ethyl-N-methylimidoformamid, (15.156) N'-{5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl} -N-ethyl-N-methylimidoformamid, (15.157) N-Cyclopropyl-3-(difluormethyl)-5-fluor- N-(2-isopropylbenzyl)- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.158) N-Cyclopropyl-N-(2- cyclopropylbenzyl)-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.159) N-(2-Tert- butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.160) N-(5- Chlor-2-ethylbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.161) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4- carboxamid, (15.162) N-Cyclopropyl-3 -(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor- 1 -methyl- 1 H- pyrazol-4-carboxamid, (15.163) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)- 1 - methyl- lH-pyrazol-4-carboxamid, (15.164) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3- (difluormethyl)-5-fluor- 1 -methyl- lH-pyrazol-4-carboxamid, (15.165) N-(2-Cyclopentyl-5-fluorbenzyl)-N- cyclopropyl-3 -(difluormethyl)-5-fiuor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.166) N-Cyclopropyl-3 - (difluormethyl)-5-fluor-N-(2-fluor-6-isopropylberizyl)-l-methyl-lH-pyrazol-4-carboxamid, (15.167) N- Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-l-methyl-lH-pyrazol-4-carboxamid, (15.168) N-Cyclopropyl-3 -(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)- 1 -methyl- 1 H-pyrazol- 4-carboxamid, (15.169) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluormethyl)-5-fluor-l- methyl-lH-pyrazol-4-carboxamid, (15.170) N-(2-Tert-butyl-5-methylbenzyl)-N-cyclopropyl-3- (difluormethyl)-5 -fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.171) N-[5 -Chlor-2-(15.154) N '- {5-Bromo-6 - [(1S) -1- (3,5-difluoro-phenyl) -ethoxy] -2-methyl-pyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.155 ) N'- {5-bromo-6- [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.156) N '- {5-bromo 6 - [(trans-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl} -N-ethyl-N-methylimidoformamide, (15.157) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- ( 2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.158) N-cyclopropyl-N- (2-cyclopropylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H- pyrazole-4-carboxamide, (15.159) N- (2-tert-butylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.160) N - (5-chloro-2-ethylbenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.161) N- (5-chloro-2- isopropylbenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.162) N-cyclopropyl-3 - (difluoromethyl) -N- (2-ethyl- 5-fluorobenzyl) -5-fluoro-1-methyl-1 H-pyrazole-4-carboxamide, (15.163) N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-fluoro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, ( 15.164) N-Cyclopropyl-N- (2-cyclopropyl-5-fluorobenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.165) N- (2-cyclopentyl- 5-fluorobenzyl) -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.166) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N (2-fluoro-6-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide, (15.167) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-5-methylbenzyl) -5- fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.168) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (2-isopropyl-5-methylbenzyl) -1-methyl-1H- pyrazole-4-carboxamide, (15.169) N-cyclopropyl-N- (2-cyclopropyl-5-methylbenzyl) -3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.170) N- (2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.171) N- [5-Chloro -2-
(trifluormethyl)benzyl] -N-cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, ( 15.172) N-Cyclopropyl-3 -(difluormethyl)-5-fluor- 1 -methyl-N- [5-methyl-2-(trifluormethyl)benzyl] - 1 H- pyrazol-4-carboxamid, (15.173) N-[2-Chlor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5- fluor-1 -methyl- lH-pyrazol-4-carboxamid, (15.174) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N- cyclopropyl-3 -(difluormethyl)-5-fiuor- 1 -methyl- 1 H-pyrazol-4-carboxamid, ( 15.175) N-Cyclopropyl-3 - (difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.176) N- Cyclopropyl-3 -(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)- 1 -methyl- 1 H-pyrazol-4-carbothioamid,(trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.172) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro 1-methyl-N- [5-methyl-2- (trifluoromethyl) benzyl] -1 H -pyrazole-4-carboxamide, (15.173) N- [2-chloro-6- (trifluoromethyl) benzyl] -N-cyclopropyl 3- (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.174) N- [3-chloro-2-fluoro-6- (trifluoromethyl) benzyl] -N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.175) N-cyclopropyl-3- (difluoromethyl) -N- (2-ethyl-4,5-dimethylbenzyl) -5- fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.176) N-cyclopropyl-3 - (difluoromethyl) -5-fluoro-N- (2-isopropylbenzyl) -1-methyl-1H-pyrazole-4 -carbothioamid,
( 15.177) 3-(Difluormethyl)-N-(7-fluor- 1 , 1 ,3 -trimethyl-2,3-dihydro- 1 H-inden-4-yl)- 1 -methyl- 1 H-pyrazol-4- carboxamid, (15.178) 3-(Difluormethyl)-N- [(3R)-7-fluor- 1 , 1 ,3 -trimethyl-2,3-dihydro- 1 H-inden-4-yl]- 1 - methyl- 1 H-pyrazol-4-carboxamid, ( 15.179) 3 -(Difluormethyl)-N- [(3 S)-7-fluor- 1 , 1 ,3-trimethyl-2,3-dihydro- 1 H-inden-4-yl]- 1 -methyl- 1 H-pyrazol-4-carboxamid, (15.180) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl- N-methylimidoformamid, ( 15.181 ) N'- {4- [(4,5-Dichlor- 1 ,3-thiazol-2-yl)oxy] -2,5-dimethylphenyl} -N-ethyl- N-methylimidoformamid, (15.182) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)- 1 ,3 -dimethyl- lH-pyrazol-5-amin. Alle genannten Mischpartner der Klassen (1) bis (15) können, wenn sie auf Grund ihrer funktionellen Gruppen dazu imstande sind, gegebenenfalls mit geeigneten Basen oder Säuren Salze bilden. (15.177) 3- (Difluoromethyl) -N- (7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) -1-methyl-1H-pyrazole-4 - carboxamide, (15.178) 3- (difluoromethyl) -N- [(3R) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1-methyl 1-H-pyrazole-4-carboxamide, (15.179) 3- (difluoromethyl) -N- [(3S) -7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene 4-yl] -1-methyl-1H-pyrazole-4-carboxamide, (15,180) N '- (2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylimidoformamide, (15.181) N'- {4- [(4,5-dichloro-1,3-thiazol-2-yl) oxy] -2,5-dimethylphenyl} -N-ethyl-N-methylimidoformamide, (15.182) N- (4-chloro-2 , 6-difluorophenyl) -4- (2-chloro-4-fluorophenyl) -1,3-dimethyl lH-pyrazol-5-amine. All of the above-mentioned mixing partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids.
Biologische Schädlingsbekämpfungsmittel als Mischungspartner Biological pesticides as a mix partner
Die Verbindungen der Formel (I) können mit biologischen Schädlingsbekämpfungsmitteln kombiniert werden. The compounds of formula (I) may be combined with biological pesticides.
Biologische Schädlingsbekämpfungsmittel umfassen insbesondere Bakterien, Pilze, Hefen, Pflanzenextrakte, und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte. Biological pesticides include, in particular, bacteria, fungi, yeasts, plant extracts, and those products formed by microorganisms, including proteins and secondary metabolites.
Biologische Schädlingsbekämpfungsmittel umfassen Bakterien wie sporenbildende Bakterien, wurzelbesiedelnde Bakterien und Bakterien, die als biologische Insektizide, Fungizide oder Nematizide wirken. Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
Beispiele für solche Bakterien, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of such bacteria which can be used as biological pesticides are:
Bacillus amyloliquefaciens, Stamm FZB42 (DSM 231179), oder Bacillus cereus, insbesondere B. cereus Stamm CNCM 1-1562 oder Bacillus firmus, Stamm 1-1582 (Accession number CNCM 1-1582) oder Bacillus pumilus, insbesondere Stamm GB34 (Accession No. ATCC 700814) und Stamm QST2808 (Accession No. NRRL B-30087), oder Bacillus subtilis, insbesondere Stamm GB03 (Accession No. ATCC SD-1397), oder Bacillus subtilis Stamm QST713 (Accession No. NRRL B-21661) oder Bacillus subtilis Stamm OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, insbesondere B. thuringiensis subspecies israelensis (serotype H-14), Stamm AM65-52 (Accession No. ATCC 1276), oder 5. thuringiensis subsp. aizawai, insbesondere Stamm ABTS- 1857 (SD-1372), oder 5. thuringiensis subsp. kurstaki Stamm HD-1, oder B. thuringiensis subsp. tenebrionis Stamm NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus Stamm AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus Stamm AQ 6047 (Acession Number NRRL 30232). Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No. NRRL B-50421) Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or 5. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or 5. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode) -PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232).
Beispiele für Pilze und Hefen, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of fungi and yeasts which can be used as biological pesticides are:
Beauveria bassiana, insbesondere Stamm ATCC 74040, Coniothyrium minitans, insbesondere Stamm CON/M/91-8 (Accession No. DSM-9660), Lecanicillium spp., insbesondere Stamm HRO LEC 12, Lecanicillium lecanii, (ehemals bekannt als Verticillium lecanii), insbesondere Stamm KV01, Metarhizium anisopliae, insbesondere Stamm F52 (DSM3884/ ATCC 90448), Metschnikowia fructicola, insbesondere Stamm NRRL Y-30752, Paecilomyces fumosoroseus (heu: Isaria fumosorosea) , insbesondere Stamm IFPC 200613, oder Stamm Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, insbesondere P. lilacinus Stamm 251 (AGAL 89/030550), Talaromyces flavus, insbesondere Stamm VI 17b, Trichoderma atroviride, insbesondere Stamm SCI (Accession Number CBS 122089), Trichoderma harzianum, insbesondere T. harzianum rifai T39. (Accession Number CNCM 1-952). Beauveria bassiana, especially strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii, (formerly known as Verticillium lecanii), in particular strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (hay: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No. ATCC 20874), Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, especially T. harzianum rifai T39. (Accession Number CNCM 1-952).
Beispiele für Viren, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: Examples of viruses that can be used or used as biological pesticides are:
Adoxophyes orana (Apfelschalenwickler) Granulosevirus (GV), Cydia pomonella (Apfelwickler) Granulosevirus (GV), Helicoverpa armigera (Baumwollkapselwurm) Nuklear Polyhedrosis Virus (NPV), Spodoptera exigua (Zuckerrübeneule) mNPV, Spodoptera frugiperda (Heerwurm) mNPV, Spodoptera littoralis (Afrikanischer Baumwollwurm) NPV. Adoxophyes orana (Apple peel winder) Granulosis virus (GV), Cydia pomonella (codling moth) Granulosis virus (GV), Helicoverpa armigera (cotton bollworm) Nuclear polyhedrosis virus (NPV), Spodoptera exigua (mNPV), Spodoptera frugiperda (armyworm) mNPV, Spodoptera littoralis (African Cotton worm) NPV.
Es sind auch Bakterien und Pilze umfasst, die als ,Inokulant' Pflanzen oder Pflanzenteilen oder Pflanzenorganen beigegeben werden und durch ihre besonderen Eigenschaften das Pflanzenwachstum und die Pflanzengesundheit fordern. Als Beispiele sind genannt: Agrobacterium spp., Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., insbesondere Burkholderia cepacia (ehemals bekannt als Pseudomonas cepacia), Gigaspora spp., oder Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., insbesondere Rhizobium trifolü, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.. Beispiele für Pflanzenextrakte und solche Produkte, die von Mikroorganismen gebildet wurden inklusive Proteine und sekundäre Stoffwechselprodukte, die als biologische Schädlingsbekämpfungsmittel eingesetzt werden bzw. verwendet werden können, sind: It also includes bacteria and fungi that are added as 'inoculant' plants or plant parts or plant organs and require by their special properties, the plant growth and plant health. Examples are: Agrobacterium spp., Azorhizobium cauUnodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., Especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp. , Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolu, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp. Examples of plant extracts and such products. which are formed by microorganisms, including proteins and secondary metabolites, which can be used as biological pesticides are:
Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense,Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa-Saponinextrakt), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,„Requiem™ Insecticide", Rotenon, Ryania/Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen-Extrakt, insbesondere Raps- oder Senfpulver. Safener als Mischpartner Allium sativum, Artemisia absinthium, Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, Chitin, Armor Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem ™ Insecticide, Rotenone, Ryania / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicacaeen extract , in particular rapeseed or mustard powder
Die Verbindungen der Formel (I) können mit Safenern kombiniert werden, wie zum Beispiel Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), Mefenpyr (-diethyl), Naphthalic anhydride, Oxabetrinil, 2-Methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamid (CAS 129531-12-0), 4-(Dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-Trimethyl-3- (dichloroacetyl)-l,3-oxazolidine (CAS 52836-31-4). Pflanzen und Pflanzenteile The compounds of the formula (I) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N - ({4 - [(methylcarbamoyl) amino] phenyl} sulfonyl) benzamide (CAS 129531- 12-0), 4- (dichloroacetyl) -l-oxa-4-azaspiro [4.5] decane (CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl) -l, 3-oxazolidine (CAS 52836-31-4). Plants and plant parts
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen), beispielsweise Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, beispielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen. According to the invention, all plants and parts of plants can be treated. Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights. Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. The plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch ein- oder mehrschichtiges Umhüllen. The treatment according to the invention of the plants and plant parts with the compounds of the formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multilayer coating.
Wie bereits oben erwähnt können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden wie Kreuzung oder Protoplastenfusion erhaltene Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff„Teile" bzw.„Teile von Pflanzen" oder„Pflanzenteile" wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften („Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein. As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "parts of plants" has been explained above.Propeas of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention Traits grown by conventional breeding, by mutagenesis or by recombinant DNA techniques, which may be varieties, breeds, biotypes and genotypes.
Transgene Pflanze, Saatgutbehandlung und Integrationsereignisse Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehrfähigkeit der Pflanzen gegen tierische und mikrobielle Schädlinge, wie Insekten, Spinnentiere, Nematoden, Milben, Schnecken, bewirkt z.B. durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus Thuringiensis (z.B. durch die Gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden, ferner eine erhöhte Abwehrfähigkeit der Pflanzen gegen pflanzenpathogene Pilze, Bakterien und/oder Viren, bewirkt z.B. durch Systemisch Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine, sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis, Triticale, Gerste, Roggen, Hafer), Mais, Soja, Kartoffel, Zuckerrüben, Zuckerrohr, Tomaten, Erbsen und andere Gemüsesorten, Baumwolle, Tabak, Raps, sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Weizen, Reis, Kartoffel, Baumwolle, Zuckerrohr, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhte Abwehrfähigkeit der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken. Transgenic Plant, Seed Treatment and Integration Events Among the preferred transgenic (genetically engineered) plants or plant species to be treated according to the invention are any plants that have obtained genetic material through genetic engineering which confer particular beneficial properties ("traits") on these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly emphasized examples of such properties are an increased resistance of the plants to animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes e.g. by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants, furthermore an increased ability to repel the plants against phytopathogenic fungi, bacteria and / or viruses, eg systemically acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins, as well as increased tolerance of the plants to certain herbicidal agents, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g., "PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soy, potato, sugar beets, sugarcane, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with special emphasis on corn, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape. Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
Pflanzenschutz - Behandlungsarten Plant protection - types of treatment
Die Behandlung der Pflanzen und Pflanzenteile mit den Verbindungen der Formel (I) erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, (Ver-) Spritzen, (Ver-)Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-) Streuen, Verschäumen, Bestreichen, Verstreichen, Injizieren, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen, usw. Es ist ferner möglich, die Verbindungen der Formel (I) nach dem Ultra-Low- Volume- Verfahren auszubringen oder die Anwendungsform oder die Verbindung der Formel (I) selbst in den Boden zu injizieren. The treatment of the plants and plant parts with the compounds of formula (I) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, (spraying) spraying (spraying), sprinkling, evaporation . Spraying, atomising, spreading, foaming, brushing, spreading, injecting, pouring, drip irrigation and, in the case of propagating material, in particular seed, further by dry pickling, wet dressing, slurry pickling, encrusting, single or multi-layer coating, etc. It is also possible to apply the compounds of the formula (I) by the ultra-low-volume method or to inject the use form or the compound of the formula (I) itself into the soil.
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d.h. Verbindungen der Formel (I) werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Schädlings abgestimmt sein sollte. Bei systemisch wirksamen Verbindungen gelangen die Verbindungen der Formel (I) auch über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der Verbindungen der Formel (I) auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen, Einmischen in den Boden oder die Nährlösung sein, d.h. der Standort der Pflanze (z.B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der Verbindungen der Formel (I) getränkt, oder durch die Bodenapplikation, d.h. die Verbindungen der Formel (I) werden in fester Form, (z.B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Verbindung der Formel (I) in einer festen Anwendungsform (z.B. als Granulat) in ein überflutetes Reisfeld sein. A preferred direct treatment of the plants is foliar application, i. Compounds of the formula (I) are applied to the foliage, wherein the treatment frequency and the application rate should be matched to the infestation pressure of the respective pest. In the case of systemically active compounds, the compounds of the formula (I) also enter the plants via the root system. The treatment of the plants is then carried out by the action of the compounds of formula (I) on the habitat of the plant. This may be, for example, by drenching, mixing into the soil or the nutrient solution, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the compounds of formula (I), or by the soil application, i. the compounds of formula (I) are incorporated in solid form (e.g., in the form of granules) at the plant site. In water rice crops, this may also be by metered addition of the compound of formula (I) in a solid form (e.g., as granules) into a flooded paddy field.
Saatgutbehandlung Die Bekämpfung von tierischen Schädlingen durch die Behandlung des Saatguts von Pflanzen ist seit langem bekannt und ist Gegenstand ständiger Verbesserungen. Dennoch ergeben sich bei der Behandlung von Saatgut eine Reihe von Problemen, die nicht immer zufriedenstellend gelöst werden können. So ist es erstrebenswert, Verfahren zum Schutz des Saatguts und der keimenden Pflanze zu entwickeln, die das zusätzliche Ausbringen von Schädlingsbekämpfungsmitteln bei der Lagerung, nach der Saat oder nach dem Auflaufen der Pflanzen überflüssig machen oder zumindest deutlich verringern. Es ist weiterhin erstrebenswert, die Menge des eingesetzten Wirkstoffs dahingehend zu optimieren, dass das Saatgut und die keimende Pflanze vor dem Befall durch tierische Schädlinge bestmöglich geschützt werden, ohne jedoch die Pflanze selbst durch den eingesetzten Wirkstoff zu schädigen. Insbesondere sollten Verfahren zur Behandlung von Saatgut auch die intrinsischen Insektiziden bzw. nematiziden Eigenschaften schädlingsresistenter bzw. - toleranter transgener Pflanzen einbeziehen, um einen optimalen Schutz des Saatguts und der keimenden Pflanze bei einem minimalen Aufwand an Schädlingsbekämpfungsmitteln zu erreichen. Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which eliminate or at least significantly reduce the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used. In particular, seed treatment methods should also incorporate the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and germinating plant with a minimum of pesticide cost.
Die vorliegende Erfindung bezieht sich daher insbesondere auch auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit einer der Verbindungen der Formel (I) behandelt wird. Das erfindungsgemäße Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen umfasst ferner ein Verfahren, in dem das Saatgut gleichzeitig in einem Vorgang oder sequentiell mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. Es umfasst ferner auch ein Verfahren, in dem das Saatgut zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wird. The present invention therefore also relates, in particular, to a method of protecting seed and germinating plants from attack by pests, by mixing the seed with one of the seeds Compounds of formula (I) is treated. The method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) and mixing partner. It also also includes a method in which the seed is treated at different times with a compound of formula (I) and mixing partner.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der Verbindungen der Formel (I) zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor tierischen Schädlingen. The invention also relates to the use of the compounds of the formula (I) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor tierischen Schädlingen mit einer Verbindung der Formel (I) behandelt wurde. Die Erfindung bezieht sich auch auf Saatgut, welches zur gleichen Zeit mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Die Erfindung bezieht sich weiterhin auf Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde. Bei Saatgut, welches zu unterschiedlichen Zeiten mit einer Verbindung der Formel (I) und Mischungspartner behandelt wurde, können die einzelnen Substanzen in unterschiedlichen Schichten auf dem Saatgut enthalten sein. Dabei können die Schichten, die eine Verbindung der Formel (I) und Mischungspartner enthalten, gegebenenfalls durch eine Zwischenschicht getrennt sein. Die Erfindung bezieht sich auch auf Saatgut, bei dem eine Verbindung der Formel (I) und Mischungspartner als Bestandteil einer Umhüllung oder als weitere Schicht oder weitere Schichten zusätzlich zu einer Umhüllung aufgebracht sind. Des Weiteren bezieht sich die Erfindung auf Saatgut, welches nach der Behandlung mit einer Verbindung der Formel (I) einem Filmcoating - Verfahren unterzogen wird, um Staubabrieb am Saatgut zu vermeiden. Furthermore, the invention relates to seed which has been treated for protection against animal pests with a compound of formula (I). The invention also relates to seed treated at the same time with a compound of formula (I) and mixing partner. The invention further relates to seed which has been treated at different times with a compound of formula (I) and mixing partner. In the case of seed which has been treated at different times with a compound of formula (I) and mixing partner, the individual substances may be contained in different layers on the seed. In this case, the layers which comprise a compound of the formula (I) and mixture partners may optionally be separated by an intermediate layer. The invention also relates to seed in which a compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I), is subjected to a film coating process in order to avoid dust abrasion on the seed.
Einer der auftretenden Vorteile, wenn eine der Verbindungen der Formel (I) systemisch wirkt, ist es, dass die Behandlung des Saatguts nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor tierischen Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. One of the advantages that occurs when one of the compounds of the formula (I) acts systemically is that the treatment of the seed protects not only the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
Ein weiterer Vorteil ist darin zu sehen, dass durch die Behandlung des Saatguts mit einer Verbindung der Formel (I) Keimung und Auflauf des behandelten Saatguts gefördert werden können. Another advantage is the fact that by treating the seed with a compound of formula (I) germination and emergence of the treated seed can be promoted.
Ebenso ist es als vorteilhaft anzusehen, dass Verbindungen der Formel (I) insbesondere auch bei transgenem Saatgut eingesetzt werden können. Likewise, it is considered to be advantageous that compounds of the formula (I) can also be used in particular in the case of transgenic seed.
Verbindungen der Formel (I) können ferner in Kombination mit Mitteln der Signaltechnologie eingesetzt werden, wodurch eine bessere Besiedlung mit Symbionten, wie zum Beispiel Rhizobien, Mycorrhiza und/oder endophytischen Bakterien oder Pilzen, stattfindet und/oder es zu einer optimierten Stickstofffixierung kommt. Compounds of the formula (I) may also be used in combination with signal technology agents, whereby a better colonization with symbionts, such as rhizobia, Mycorrhiza and / or endophytic bacteria or fungi, takes place and / or there is an optimized nitrogen fixation.
Die Verbindungen der Formel (I) eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Getreide (z. B. Weizen, Gerste, Roggen, Hirse und Hafer), Mais, Baum-wolle, Soja, Reis, Kartoffeln, Sonnenblume, Kaffee, Tabak, Canola, Raps, Rübe (z.B. Zuckerrübe und Futterrübe), Erdnuss, Gemüse (z. B. Tomate, Gurke, Bohne, Kohlgewächse, Zwiebeln und Salat), Obstpflanzen, Rasen und Zierpflanzen. Besondere Bedeutung kommt der Behandlung des Saatguts von Getreide (wie Weizen, Gerste, Roggen und Hafer), Mais, Soja, Baumwolle, Canola, Raps und Reis zu. Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit einer Verbindung der Formel (I) eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere Insektiziden bzw. nematiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikro- Organismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von trans-genem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt. The compounds of the formula (I) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of seeds of cereals (such as wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice. As already mentioned above, the treatment of transgenic seed with a compound of the formula (I) is also of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal or nematicidal properties. The heterologous genes in transgenic seed can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird die Verbindung der Formel (I) auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem es so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen. Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hülle, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem lagerfähigen Feuchtigkeitsgehalt getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z.B. mit Wasser behandelt und dann erneut getrocknet wurde, zum Beispiel Priming. In the context of the present invention, the compound of the formula (I) is applied to the seed. Preferably, the seed is treated in a state where it is so stable that no damage occurs during the treatment. In general, the treatment of the seed can be done at any time between harvesting and sowing. Usually, seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp. For example, seed may be used that has been harvested, cleaned and dried to a moisture content that is storable. Alternatively, seed may also be used which, after drying, e.g. treated with water and then dried again, for example priming.
Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge der auf das Saatgut aufgebrachten Verbindung der Formel (I) und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. Die Verbindungen der Formel (I) werden in der Regel in Form einer geeigneten Formulierung auf das Saatgut aufgebracht. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt. In general, when treating seed, care must be taken to ensure that the amount of compound of formula (I) and / or other additives applied to the seed is not such as to affect the germination of the seed or to damage the resulting plant becomes. This is especially important for active ingredients, which can show phytotoxic effects in certain application rates. The compounds of the formula (I) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
Die Verbindungen der Formel (I) können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. The compounds of the formula (I) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, and also ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man Verbindungen der Formel (I) mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. These formulations are prepared in a known manner by mixing compounds of formula (I) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe. Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutyl-naphthalin-Sulfonate. Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor-zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid Blockpolymere, Alkylphenolpolyglykolether sowie Tri- stryrylphenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- Formaldehydkondensate. Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates. Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate. Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu- Hertingen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Suitable secondary thickeners which may be present in the seed-dressing formulations of the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
Als Gibberelline, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen vorzugsweise die Gibberelline AI, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler „Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401- 412). Gibberellins which may be present in the seed dressing formulations which can be used in accordance with the invention are preferably the gibberellins AI, A3 (= gibberellic acid), A4 and A7, particularly preferably gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).
Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vorherigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art eingesetzt werden. So lassen sich die Konzentrate oder die daraus durch Verdünnen mit Wasser erhältlichen Zubereitungen einsetzen zur Beizung des Saatgutes von Getreide, wie Weizen, Gerste, Roggen, Hafer und Triticale, sowie des Saatgutes von Mais, Reis, Raps, Erbsen, Bohnen, Baumwolle, Sonnenblumen, Soja und Rüben oder auch von Gemüsesaatgut der verschiedensten Natur. Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder deren verdünnte Anwendungsformen können auch zum Beizen von Saatgut transgener Pflanzen eingesetzt werden. The seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds. Thus, the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature. The seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder daraus hergestellten Anwendungsformen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht. Im einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer im diskontinuierlichem oder kontinuierlichem Betrieb gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungsvorgang an. For the treatment of seed with the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom, all mixing devices which can usually be used for the dressing can be considered. Specifically, the pickling is done by placing the seed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed. Optionally, a drying process follows.
Die Aufwandmenge an den erfindungsgemäß verwendbaren Beizmittel-Formulierungen kann inner-halb eines größeren Bereiches variiert werden. Sie richtet sich nach dem jeweiligen Gehalt der Verbindungen der Formel (I) in den Formulierungen und nach dem Saatgut. Die Aufwandmengen bei der Verbindung der Formel (I) liegen im Allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 15 g pro Kilogramm Saatgut. The application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) in the formulations and on the seed. The application rates at the connection of the formula (I) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
Tiergesundheit animal Health
Auf dem Gebiet der Tiergesundheit, d.h. dem Gebiet der Tiermedizin, sind die Verbindungen der Formel (I) gegen Tierparasiten, insbesondere Ektoparasiten oder Endoparasiten, wirksam. Der Begriff Endoparasiten umfasst insbesondere Helminthen und Protozoa wie Kokzidien. Ektoparasiten sind typischerweise und bevorzugt Arthropoden, insbesondere Insekten und Akariden. In the field of animal health, i. In the veterinary field, the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term endoparasite includes in particular helminths and protozoa such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects and acarids.
Auf dem Gebiet der Tiermedizin eignen sich die Verbindungen der Formel (I), die eine günstige Toxizität gegenüber Warmblütern aufweisen, für die Bekämpfung von Parasiten, die in der Tierzucht und Tierhaltung bei Nutztieren, Zuchttieren, Zootieren, Laboratoriumstieren, Versuchstieren und Haustieren auftreten. Sie sind gegen alle oder einzelne Entwicklungsstadien der Parasiten wirksam. In the field of veterinary medicine, the compounds of formula (I), which have favorable toxicity to warm-blooded animals, are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.
Zu den landwirtschaftlichen Nutztieren zählen zum Beispiel Säugetiere wie Schafe, Ziegen, Pferde, Esel, Kamele, Büffel, Kaninchen, Rentiere, Damhirsche und insbesondere Rinder und Schweine; Geflügel wie Truthähne, Enten, Gänse und insbesondere Hühner; Fische und Krustentiere, z.B. in der Aquakultur und auch Insekten wie Bienen. Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; Poultry such as turkeys, ducks, geese and, in particular, chickens; Fish and shellfish, e.g. in aquaculture and also insects like bees.
Zu den Haustieren zählen zum Beispiel Säugetiere wie Hamster, Meerschweinchen, Ratten, Mäuse, Chinchillas, Frettchen und insbesondere Hunde, Katzen, Stubenvögel, Reptilien, Amphibien und Aquariumfische. The domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds, reptiles, amphibians and aquarium fish.
Gemäß einer bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Säugetiere verabreicht. In a preferred embodiment, the compounds of formula (I) are administered to mammals.
Gemäß einer weiteren bevorzugten Ausführungsform werden die Verbindungen der Formel (I) an Vögel, nämlich Stubenvögel und insbesondere Geflügel, verabreicht. According to a further preferred embodiment, the compounds of the formula (I) are administered to birds, namely caged birds and in particular poultry.
Durch Verwendung der Verbindungen der Formel (I) für die Bekämpfung von Tierparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig und dergleichen) verringert bzw. vorgebeugt werden, so dass eine wirtschaftlichere und einfachere Tierhaltung ermöglicht wird und ein besseres Wohlbefinden der Tiere erzielbar ist. By using the compounds of formula (I) for the control of animal parasites disease, deaths and reductions in performance (in meat, milk, wool, hides, eggs, honey and the like) should be reduced or prevented, so that a more economical and easier animal husbandry allows and a better well-being of the animals is achievable.
In Bezug auf das Gebiet der Tiergesundheit bedeutet der Begriff "Bekämpfung" oder "bekämpfen", dass durch die Verbindungen der Formel (I) wirksam das Auftreten des jeweiligen Parasiten in einem Tier, das mit solchen Parasiten in einem harmlosen Ausmaß infiziert ist, reduziert werden kann. Genauer gesagt bedeutet "bekämpfen" im vorliegenden Zusammenhang, dass die Verbindung der Formel (I) den jeweiligen Parasiten abtöten, sein Wachstum verhindern oder seine Vermehrung verhindern kann. Zu den Arthropoden zählen: aus der Ordnung Anoplurida, zum Beispiel Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; aus der Ordnung Mallophagida und den Unterordnungen Amblycerina and Ischnocerina, zum Beispiel Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; aus der Ordnung Diptera und den Unterordnungen Nematocerina und Brachycerina, zum Beispiel Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; aus der Ordnung Siphonapterida, zum Beispiel Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; aus der Ordnung Heteropterida, zum Beispiel Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.; sowie Lästlinge und Hygieneschädlinge aus der Ordnung Blattarida. With regard to the field of animal health, the term "control" or "combat" means that the compounds of formula (I) effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent can. More specifically, "combating" in the present context means that the compound of formula (I) can kill the respective parasite, prevent its growth or prevent its replication. The arthropods include: from the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia Spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. , Fannia spp., Glossina spp., Calliphora spp., Lucilla spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; from the order Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; from the order Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .; as well as pests and hygiene pests from the order Blattarida.
Weiterhin zählen zu den Arthropoden: Furthermore, the arthropods include:
Aus der Unterklasse Akari (Acarina) und der Ordnung Metastigmata, zum Beispiel aus der Familie Argasidae, wie Argas spp., Ornithodorus spp., Otobius spp., aus der Familie Ixodidae, wie Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (die ursprüngliche Gattung der mehrwirtigen Zecken); aus der Ordnung Mesostigmata, wie Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; aus der Ordnung Actinedida (Prostigmata), zum Beispiel Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp.; und aus der Ordnung Acaridida (Astigmata), zum Beispiel Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.. From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of multi-pronged ticks); from the order Mesostigmata, such as Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; from the order Actinedida (Prostigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Neotrombiculla spp., Listrophorus spp .; and from the order Acaridida (Astigmata), for example Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp. , Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
Zu parasitären Protozoen zählen: Parasitic protozoa include:
Mastigophora (Flagellata), wie zum Beispiel Trypanosomatidae, zum Beispiel Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, wie zum Beispiel Trichomonadidae, zum Beispiel Giardia lamblia, G. canis; Sarcomastigophora (Rhizopoda), wie Entamoebidae, zum Beispiel Entamoeba histolytica, Hartmanellidae, zum Beispiel Acanthamoeba sp., Harmanella sp.; Mastigophora (Flagellata), such as Trypanosomatidae, for example Trypanosoma b. brucei, Tb gambiense, Tb rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica such as Trichomonadidae, for example Giardia lamblia, G. canis; Sarcomastigophora (Rhizopoda) such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp .;
Apicomplexa (Sporozoa), wie Eimeridae, zum Beispiel Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E. canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis, E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E. media, E. meleagridis, E. meleagrimitis, E. mitis, E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, E. pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E. spec, E. stiedai, E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec, Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec, I. suis, Cystisospora spec, Cryptosporidium spec, insbesondere C. parvum; wie Toxoplasmadidae, zum Beispiel Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; wie Sarcocystidae, zum Beispiel Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec, S. suihominis, wie Leucozoidae, zum Beispiel Leucozytozoon simondi, wie Plasmodiidae, zum Beispiel Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P. vivax, P. spec, wie Piroplasmea, zum Beispiel Babesia argentina, B. bovis, B. canis, B. spec, Theileria parva, Theileria spec, wie Adeleina, zum Beispiel Hepatozoon canis, H. spec. Apicomplexa (Sporozoa), such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E. gallopavonis , E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. stiedai E. suis, E. tenella, E. truncata, E. truttae, E. zuernii, Globidium spec., Isospora belli, I. canis, I. felis, I. ohioensis, I. rivolta, I. spec., I. suis , Cystisospora spec., Cryptosporidium spec., Especially C. parvum; such as Toxoplasmadidae, for example Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; such as Sarcocystidae, for example Sarcocystis bovicanis, S. bovihominis, S. ovicanis, S. ovifelis, S. neurona, S. spec., S. suihominis, such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
Zu pathogenen Endoparasiten, bei denen es sich um Helminthen handelt, zählen Plattwürmer (z.B. Monogenea, Cestodes und Trematodes), Rundwürmer, Acanthocephala und Pentastoma. Dazu zählen: Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Pathogenic endoparasites, which are helminths, include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma. These include: Monogenea: e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp .;
Cestodes: aus der Ordnung Pseudophyllidea zum Beispiel: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.; aus der Ordnung Cyclophyllida zum Beispiel: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.; Cestodes: from the order Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp .; from the order Cyclophyllida for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp. , Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp .;
Trematodes: aus der Klasse Digenea zum Beispiel: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp.; Trematodes: from the genus Digenea for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Omithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fascioloides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp. , Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .;
Rundwürmer: Trichinellida zum Beispiel: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp.; aus der Ordnung Tylenchida zum Beispiel: Micronema spp., Strongyloides spp.; aus der Ordnung Rhabditida zum Beispiel: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.; aus der Ordnung Spirurida zum Beispiel: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.; Roundworms: Trichinellida for example: Trichuris spp., Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosoides spp., Trichinella spp .; from the order Tylenchida for example: Micronema spp., Strongyloides spp .; from the order Rhabditida, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp. , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Teladorsagia spp., Marshallagia spp , Cooperia spp., Nippostrongylus spp., Heligmosomoides spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp .; from the order Spirurida for example: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp .; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp .; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp .; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp .;
Acanthocephala: aus der Ordnung Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung Polymorphida zum Beispiel: Filicollis spp.; aus der Ordnung Moniliformida zum Beispiel: Moniliformis spp.; aus der Ordnung Echinorhynchida zum Beispiel Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; Acanthocephala: from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp .; from the order Echinorhynchida for example Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp .;
Pentastoma: aus der Ordnung Porocephalida zum Beispiel Linguatula spp.. Auf dem Gebiet der Tiermedizin und der Tierhaltung erfolgt die Verabreichung der Verbindungen der Formel (I) nach allgemein fachbekannten Verfahren, wie enteral, parenteral, dermal oder nasal in Form von geeigneten Präparaten. Die Verabreichung kann prophylaktisch oder therapeutisch erfolgen. So bezieht sich eine Ausführungsform der vorliegenden Erfindung auf die Verwendung einer Verbindung der Formel (I) als Arzneimittel. Pentastoma: from the order Porocephalida for example Linguatula spp .. In the field of veterinary medicine and animal husbandry, the compounds of the formula (I) are administered by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. The administration can be prophylactic or therapeutic. Thus, one embodiment of the present invention relates to the use of a compound of formula (I) as a medicament.
Ein weiterer Aspekt bezieht sich auf die Verwendung einer Verbindung der Formel (I) als Antiendoparasitikum, insbesondere als ein Helminthizid oder ein Mittel gegen Protozoen. Verbindungen der Formel (I) eignen sich für die Verwendung als Antiendoparasitikum, insbesondere als ein Helminthizid oder Mittel gegen Protozoen, beispielsweise in der Tierzucht, in der Tierhaltung, in Ställen und auf dem Hygienesektor. Another aspect relates to the use of a compound of formula (I) as an antiendoparasitic agent, in particular as a helminthicide or antiprotozoal agent. Compounds of the formula (I) are suitable for use as antiendoparasitic agents, in particular as a helminthicide or antiprotozoal agents, for example in animal breeding, animal husbandry, in stables and in the hygiene sector.
Ein weiterer Aspekt wiederum betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder ein Akarizid Ein weiterer Aspekt betrifft die Verwendung einer Verbindung der Formel (I) als Antiektoparasitikum, insbesondere ein Arthropodizid wie ein Insektizid oder Akarizid, zum Beispiel in der Tierhaltung, in der Tierzucht, in Ställen oder auf dem Hygienesektor. A further aspect in turn relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide. Another aspect relates to the use of a compound of the formula (I) as an antiectica, in particular an arthropodicide such as an insecticide or acaricide For example, in animal husbandry, in animal husbandry, in stables or in the hygiene sector.
Vektorkontrolle vector control
Die Verbindungen der Formel (I) können auch in der Vektorkontrolle eingesetzt werden. Ein Vektor im Sinne der vorliegenden Erfindung ist ein Arthropode, insbesondere ein Insekt oder Arachnide, der in der Lage ist, Krankheitserreger wie z. B. Viren, Würmer, Einzeller und Bakterien aus einem Reservoir (Pflanze, Tier, Mensch, etc.) auf einen Wirt zu übertragen. Die Krankheitserreger können entweder mechanisch (z.B. Trachoma durch nicht-stechende Fliegen) auf einem Wirt, oder nach Injektion (z.B. Malaria-Parasiten durch Mücken) in einen Wirt übertragen werden. Beispiele für Vektoren und die von ihnen übertragenen Krankheiten bzw. Krankheitserreger sind: The compounds of formula (I) can also be used in vector control. A vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such. As viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer. The pathogens may be transferred to a host either mechanically (e.g., trachoma by non-stabbing flies) on a host, or after injection (e.g., malaria parasites by mosquitoes). Examples of vectors and their transmitted diseases or pathogens are:
1) Mücken 1) mosquitoes
- Anopheles: Malaria, Filariose; - Anopheles: malaria, filariasis;
- Culex: Japanische Encephalitis, Filariasis, weitere virale Erkrankungen, Übertragung von Würmern; - Culex: Japanese encephalitis, filariasis, other viral diseases, transmission of worms;
- Aedes: Gelbfieber, Dengue-Fieber, Filariasis, weitere virale Erkrankungen; - Simulien: Übertragung von Würmern insbesondere Onchocerca volvulus; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases; - Simulia: transmission of worms, in particular Onchocerca volvulus;
2) Läuse: Hautinfektionen, Fleckfieber (epidemic typhus); 2) lice: skin infections, typhus (epidemic typhus);
3) Flöhe: Pest, endemisches Fleckfieber; 3) Fleas: plague, endemic typhus fever;
4) Fliegen: Schlafkrankheit (Trypanosomiasis); Cholera, weitere bakterielle Erkrankungen; 5) Milben: Acariose, Fleckfieber, Rickettsipocken, Tularämie, Saint-Louis-Enzephalitis, virale Hirnhautentzündung (FSME), Krim-Kongo-Fieber, Borreliose; 4) flies: sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases; 5) mites: acariosis, typhus, rickettsipox, tularemia, Saint-Louis encephalitis, viral meningitis (TBE), Crimean Congo fever, Lyme disease;
6) Zecken: Borelliosen wie Borrelia duttoni, Frühsommer-Meningoenzephalitis, Q-Fieber (Coxiella burnetii), Babesien (Babesia canis canis). Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten wie Aphiden, Fliegen, Zikaden oder Thripse, die Pflanzenviren auf Pflanzen übertragen können. Weitere Vektoren, die Pflanzenviren übertragen können, sind Spinnmilben, Läuse, Käfer und Nematoden. 6) Ticks: Borellioses such as Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis). Examples of vectors in the context of the present invention are insects such as aphids, flies, cicadas or thrips, which can transmit plant viruses to plants. Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
Weitere Beispiele für Vektoren im Sinne der vorliegenden Erfindung sind Insekten und Arachniden wie Mücken, insbesondere der Gattungen Aedes, Anopheles, z.B. A. gambiae, A. arabiensis, A. funestus, A. dirus (Malaria) und Culex, Läuse, Flöhe, Fliegen, Milben und Zecken, die Krankheitserreger auf Tiere und/oder Menschen übertragen können. Further examples of vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, e.g. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
Eine Vektorkontrolle ist auch möglich, wenn die Verbindungen der Formel (I) Resistenz-brechend sind. Vector control is also possible when the compounds of formula (I) are resistance-disrupting.
Verbindungen der Formel (I) sind zur Verwendung in der Prävention von Krankheiten bzw. vor Krankheitserregern, die durch Vektoren übertragen werden, geeignet. Somit ist ein weiterer Aspekt der vorliegenden Erfindung die Verwendung von Verbindungen der Formel (I) zur Vektorkontrolle, z.B. in der Landwirtschaft, im Gartenbau, in Forsten, in Gärten und Freizeiteinrichtungen sowie im Vorratsund Materialschutz. Compounds of formula (I) are suitable for use in the prevention of disease or pathogens transmitted by vectors. Thus, another aspect of the present invention is the use of compounds of formula (I) for vector control, e.g. in agriculture, horticulture, forests, gardens and recreational facilities, as well as in the supply and protection of materials.
Schutz von technischen Materialen Protection of technical materials
Die Verbindungen der Formel (I) eignen sich zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten, z.B. aus der Ordnung Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera und Zygentoma. The compounds of formula (I) are useful for protecting engineering materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt. Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred.
In einer weiteren Ausführungsform werden die Verbindungen der Formel (I) zusammen mit mindestens einem weiteren Insektizid und/oder mindestens einem Fungizid eingesetzt. In a further embodiment, the compounds of the formula (I) are used together with at least one further insecticide and / or at least one fungicide.
In einer weiteren Ausführungsform liegen die Verbindungen der Formel (I) als ein anwendungsfertiges (ready-to-use) Schädlingsbekämpfungsmittel vor, d.h., es kann ohne weitere Änderungen auf das entsprechende Material aufgebracht werden. Als weitere Insektizide oder als Fungizide kommen insbesondere die oben genannten in Frage. Überraschenderweise wurde auch gefunden, dass die Verbindungen der Formel (I) zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die Verbindungen der Formel (I) allein oder in Kombinationen mit anderen Wirkstoffen als Antifouling-Mittel eingesetzt werden. In a further embodiment, the compounds of the formula (I) are present as ready-to-use pesticides, ie, they can be applied to the corresponding material without further changes. As further insecticides or as fungicides in particular the above-mentioned in question. Surprisingly, it has also been found that the compounds of the formula (I) can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. Likewise, the compounds of the formula (I) can be used alone or in combination with other active substances as antifouling agents.
Bekämpfung von tierischen Schädlingen auf dem Hygienesektor Control of animal pests in the hygiene sector
Die Verbindungen der Formel (I) eignen sich zur Bekämpfung von tierischen Schädlingen auf dem Hygienesektor. Insbesondere kann die Erfindung im Haushalts-, Hygiene- und Vorratsschutz verwendet werden, vor allem zur Bekämpfung von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen vorkommen. Zur Bekämpfung der tierischen Schädlinge werden die Verbindungen der Formel (I) allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie in Haushaltsinsektizid-Produkten verwendet. Die Verbindungen der Formel (I) sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. Zu diesen Schädlingen gehören beispielsweise Schädlinge aus der Klasse Arachnida, aus den Ordnungen Scorpiones, Araneae und Opiliones, aus den Klassen Chilopoda und Diplopoda, aus der Klasse Insecta die Ordnung Blattodea, aus den Ordnungen Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria oder Orthoptera, Siphonaptera und Zygentoma und aus der Klasse Malacostraca die Ordnung Isopoda. Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. The compounds of the formula (I) are suitable for controlling animal pests in the hygiene sector. In particular, the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins. To combat animal pests, the compounds of formula (I) are used alone or in combination with other active ingredients and / or excipients. Preferably, they are used in household insecticide products. The compounds of formula (I) are active against sensitive and resistant species and against all stages of development. These pests include, for example, pests of the class Arachnida, from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda. Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
Erläuterung der Verfahren und Zwischenprodukte Explanation of processes and intermediates
Verbindungen der allgemeinen Formel (I) Compounds of the general formula (I)
können erhalten werden, in dem man Carbonsäuren der allgemeinen Formel (II) can be obtained by reacting carboxylic acids of the general formula (II)
mit 1 -Aminocyclopropancarbothioamid der Formel VII) with 1-aminocyclopropanecarbothioamide of the formula VII)
in Gegenwart eines Kondensationsreagenzes, wie z.B. [Benztriazol-l -yloxy(dimethylamino)methylene]- dimethyl-ammonium hexafluorphosphat, umsetzt. in the presence of a condensation reagent, e.g. [Benztriazole-l-oxyloxy (dimethylamino) methylene] - dimethyl ammonium hexafluorophosphate.
Indolcarbonsäuren der Formeln (IIa) sind zum Teil bekannt (vgl. z.B. WO-A-2012/119984). In Analogie zum in WO-A-2012/119984 beschriebenen Verfahren können auch neue Verbindungen der Formel (IIa) nach Schema 1 erhalten werden. Dabei steht L4 für Wasserstoff. Indolecarboxylic acids of the formulas (IIa) are known in some cases (cf., for example, WO-A-2012/119984). Analogously to the process described in WO-A-2012/119984, it is also possible to obtain novel compounds of the formula (IIa) according to Scheme 1. Where L 4 is hydrogen.
Schema 1 Scheme 1
(IIa)  (IIa)
Benzimidazolcarbonsäuren der Formeln (IIb) sind neu und können z.B. nach Schema 2 erhalten werden.  Benzimidazole carboxylic acids of formula (IIb) are novel and may be e.g. are obtained according to Scheme 2.
Schema 2 Scheme 2
Benzimidazolderivate der Formel (IIb) werden aus Verbindungen der Formel (A-l l) durch Hydrolyse z.B. mit NaOH erhalten. Verbindungen der Formel (A-l l) können aus Verbindungen der Formel (A- 10b) durch Umsetzung in Gegenwart von sauren Katalysatoren wie z.B. 4-Toluolsulfonsäurehydrat, Salzsäure oder Essigsäure erhalten werden. Die Umsetzung erfolgt unter den in der Literatur für analoge Verbindungen bekannten Bedingungen (vgl. z.B. EP1602648, Example 4; Journal of Medicinal Chemistry, 55 (2012) 9089 - 9106).  Benzimidazole derivatives of the formula (IIb) are prepared from compounds of the formula (A-II) by hydrolysis, e.g. obtained with NaOH. Compounds of formula (A-1 L) may be prepared from compounds of formula (A-10b) by reaction in the presence of acidic catalysts, e.g. 4-Toluolsulfonsäurehydrat, hydrochloric acid or acetic acid are obtained. The reaction is carried out under conditions known in the literature for analogous compounds (see, e.g., EP1602648, Example 4, Journal of Medicinal Chemistry, 55 (2012) 9089-9106).
Verbindungen der Formel (A-lOb) können zusammen mit Verbindungen der Formel (A-lOa) erhalten werden, indem man zunächst Verbindungen der Formel (A-8) mit Thionylchlorid umsetzt und das nicht isolierte Intermediat anschließend mit 1 ,2-Diaminophenylderivaten der Formel (A-9) umsetzt. Die Umsetzung erfolgt unter den in der Literatur für analoge Verbindungen bekannten Bedingungen (vgl. z.B. EP 1602648, Example 4; Journal of Medicinal Chemistry, 55 (2012) 9089 - 9106). Compounds of the formula (A-10b) can be obtained together with compounds of the formula (A-10a) by first reacting compounds of the formula (A-8) with thionyl chloride and then the uninsulated intermediate with 1, 2-diaminophenyl derivatives of the formula (A-9). The reaction is carried out under the conditions known in the literature for analogous compounds (see, for example, EP 1602648, Example 4: Journal of Medicinal Chemistry, 55 (2012) 9089-9106).
1 ,2-Diaminophenylderivate der Formel (A-9) sind bekannt (vgl. z.B. WO2012/119984). Carbonsäuren der Formel (A-8) können durch Hydrolyse von Estern der Formel (A-7) erhalten werden. 1,2-Diaminophenyl derivatives of formula (A-9) are known (see for example WO2012 / 119984). Carboxylic acids of the formula (A-8) can be obtained by hydrolysis of esters of the formula (A-7).
Carbonsäuren der Formel (A-8) lassen sich in Analogie zu literaturbekannten Verfahren durch Esterspaltung aus Verbindungen der allgemeinen Struktur (A-7) herstellen (z. B. durch NaOH oder LiOH. Weitere Methoden siehe z.B. Tetrahedron 49 (1993) 3691-3748). Carboxylic acids of the formula (A-8) can be prepared analogously to processes known from the literature by ester cleavage from compounds of the general structure (A-7) (for example by NaOH or LiOH.) See Tetrahedron 49 (1993) 3691-3748 for further methods ).
Verbindungen der Formel (A-7) sind durch Umsetzung von Aminen der Formel (A-4) mit Ethyl 2- chloro-2-oxo-acetat zugänglich. Die Umsetzung erfolgt unter den in der Literatur für analoge Verbindungen bekannten Bedingungen (vgl. z.B. EP1997813, Seite 210, Example 8 Stepl). Compounds of the formula (A-7) can be obtained by reacting amines of the formula (A-4) with ethyl 2-chloro-2-oxo-acetate. The reaction is carried out under the conditions known in the literature for analogous compounds (see, for example, EP1997813, page 210, Example 8 Stepl).
Halogenalkyl substituierte Amine der allgemeine Formel (A-4) sind kommerziell erhältlich, literaturbekannt oder können anhand literaturbekannter Verfahren synthetisiert werden (vgl. z.B. WO2012/119984). 1-Aminocyclopropancarbothioamid der Formel (VII) (CAS-Nr. 1159877-97-0; WO2009/070485) ist kommerziell erhältlich. Haloalkyl-substituted amines of the general formula (A-4) are commercially available, known from the literature or can be synthesized by methods known from the literature (cf., for example, WO2012 / 119984). 1-aminocyclopropanecarbothioamide of the formula (VII) (CAS No. 1159877-97-0, WO2009 / 070485) is commercially available.
Die erfindungsgemäßen Verfahren zur Herstellung der neuen Verbindungen der Formel (I) werden vorzugsweise unter Verwendung eines Verdünnungsmittels durchgeführt. Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren kommen neben Wasser alle inerten Lösungsmittel in Frage. Als Beispiele sind zu nennen:. Halogenkohlenwasserstoffe (z.B. Chlorkohlenwasserstoffe, wie Tetraethylen, Tetrachlorethan, Dichlorpropan, Methylenchlorid, Dichlorbutan, Chloroform, Tetrachlorkohlenstoff, Trichlorethan, Trichlorethylen, Pentachlorethan, Difluorbenzol, 1 ,2-Dichlorethan, Chlorbenzol, Brombenzol, Dichlorbenzol, Chlortoluol, Trichlorbenzol), Alkohole (z.B. Methanol, Ethanol, Isopropanol, Butanol), Ether (z.B. Ethylpropylether, Methyl-tert-butylether, Anisol, Phenetol, Cyclohexylmethylether, Dimethylether, Diethylether, Diproplether, Diisopropylether, Di-n-butylether, Diisobutylether, Diisoamylether, Ethylenglycoldimethylether, Tetrahydrofuran, 1 ,4-Dioxan, Dichlordiethylether und Polyether des Ethylenoxids und/oder Propylenoxids), Amine (z.B. Trimethyl-, Triethyl-, Tripropyl-, Tributylamin, N-Methylmorpholin, Pyridin und Tetramethylendiamin), Nitrokohlenwasserstoffe (z.B. Nitromethan, Nitroethan, Nitropropan, Nitrobenzol, Chlornitrobenzol, o- Nitrotoluol); Nitrile (wie z.B. Acetonitril, Propionitril, Butyronitril, Isobutyronitril, Benzonitril, m- Chlorbenzonitril), Tetrahydrothiophendioxid, Dimethylsulfoxid, Tetramethylensulfoxid, Dipropylsulfoxid, Benzylmethylsulfoxid, Diisobutylsulfoxid, Dibutylsulfoxid, Diisoamylsulfoxid, Sulfone (z.B. Dimethyl-, Diethyl-, Dipropyl-, Dibutyl-, Diphenyl-, Dihexyl-, Methylethyl-, Ethylpropyl- , Ethylisobutyl- und Pentamethylensulfon), aliphatische, cycloaliphatische oder aromatische Kohlenwasserstoffe (z.B. Pentan, Hexan, Heptan, Oktan, Nonan und technische Kohlenwasserstoffe), ferner sogenannte "White Spirits" mit Komponenten mit Siedepunkten im Bereich von beispielsweise 40°C bis 250°C, Cymol, Benzinfraktionen 5 innerhalb eines Siedeinterwalles von 70°C bis 190°C, Cyclohexan, Methylcyclohexan, Petrolether, Ligroin, Octan, Benzol, Toluol, Chlorbenzol, Brombenzol, Nitrobenzol, Xylol, Ester (z.B. Methyl-, Ethyl-, Butyl-, Isobutylacetat, Dimethyl-, Dibutyl-, Ethylencarbonat); Amide (z.B. Hexamethylenphosphorsäuretriamid, Formamid, N-Methyl-formamid, Ν,Ν-Dimethyl-formamid, N,N-Dipropyl-formamid, Ν,Ν-Dibutyl-formamid, N-Methyl-pyrrolidin, N- Methyl-caprolactam, l,3-Dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidin, Octylpyrrolidon,The processes according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention, besides water, are all inert solvents. As examples are :. Halogenated hydrocarbons (eg chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (eg. Ethanol, isopropanol, butanol), ethers (eg ethyl propyl ether, methyl tert-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dipropl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, 1, 4- Dioxane, dichloro diethyl ether and polyethers of ethylene oxide and / or propylene oxide), amines (eg trimethyl-, triethyl-, tripropyl-, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine), nitrohydrocarbons (eg nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o - nitrotoluene); Nitriles (such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulfoxide, tetramethylene sulfoxide, dipropyl sulfoxide, benzylmethyl sulfoxide, diisobutyl sulfoxide, dibutyl sulfoxide, diisoamyl sulfoxide, sulfones (eg dimethyl, diethyl, dipropyl, dibutyl, Diphenyl, dihexyl, methylethyl, ethylpropyl, ethylisobutyl and pentamethylene sulfone), aliphatic, cycloaliphatic or aromatic hydrocarbons (eg pentane, hexane, heptane, octane, nonane and technical hydrocarbons), also known as "white spirits" with components having boiling points in the range of, for example, 40 ° C to 250 ° C, cymene, gasoline fractions 5 within a boiling rampart of 70 ° C to 190 ° C, cyclohexane, methylcyclohexane, petroleum ether, ligroin, octane, benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene, xylene, Esters (eg methyl, ethyl, butyl, isobutyl acetate, dimethyl, dibutyl, ethylene carbonate); Amides (eg, hexamethylenephosphoric triamide, formamide, N-methylformamide, Ν, Ν-dimethylformamide, N, N-dipropylformamide, Ν, Ν-dibutylformamide, N-methylpyrrolidine, N-methyl-caprolactam, l , 3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidine, octylpyrrolidone,
Octylcaprolactam, l,3-Dimethyl-2-imidazolindion, N-Formyl-piperidin, Ν,Ν'-Diformyl-piperazin) und Ketone (z.B. Aceton, Acetophenon, Methylethylketon, Methylbutylketon). Octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, Ν, Ν'-diformyl-piperazine) and ketones (e.g., acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone).
Selbstverständlich kann man das erfindungsgemäße Verfahren auch in Gemischen der genannten Lösungs- und Verdünnungsmittel durchführen. Of course, the process according to the invention can also be carried out in mixtures of the solvents and diluents mentioned.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen zwischen -30°C und +150°C, vorzugsweise zwischen -10°C und +100°C. Das erfindungsgemäße Verfahren wird im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, das erfindungsgemäße Verfahren unter erhöhtem oder vermindertem Druck - im Allgemeinen bei absoluten Drücken zwischen 0, 1 bar und 15 bar - durchzuführen. The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between -10 ° C and + 100 ° C. The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally at absolute pressures between 0.1 and 15 bar.
Zur Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe im Allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem größeren Überschuss zu verwenden. Die Umsetzung wird im Allgemeinen in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsmittels, gegebenenfalls auch unter einer Schutzgas-Atmosphäre (z.B. unter Stickstoff, Argon oder Helium) durchgeführt und das Reaktionsgemisch wird im Allgemeinen mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Herstellungsbeispiele). To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature. The workup is carried out by customary methods (see the preparation examples).
Als basische Reaktionshilfsmittel zur Durchführung der erfindungsgemäßen Verfahren können alle geeigneten Säurebindemittel eingesetzt werden. Als Beispiele sind zu nennen: Erdalkali- oder Alkalimetallverbindungen (z.B. Hydroxide, Hydride, Oxide und Carbonate des Lithiums, Natriums, Kaliums, Magnesiums, Calciums und Bariums), Amidinbasen oder Guanidinbasen (z.B. 7-Methyl- 1,5,7- triaza-bicyclo(4.4.0)dec-5-en (MTBD); Diazabicyclo(4.3.0)nonen (DBN), Diazabicyclo(2.2.2)octan (DABCO), 1,8-Diazabicyclo(5.4.0)undecen (DBU), Cyclohexyltetrabutyl-guanidin (CyTBG), Cyclohexyltetramethylguanidin (CyTMG), N,N,N,N-Tetramethyl-l,8-naphthalindiamin,As basic reaction auxiliaries for carrying out the process according to the invention, it is possible to use all suitable acid binders. Examples which may be mentioned are: alkaline earth or alkali metal compounds (eg hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium), amidine bases or guanidine bases (eg 7-methyl-1,5,7-triaza- bicyclo (4.4.0) dec-5-ene (MTBD), diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1,8-diazabicyclo (5.4.0) undecene (DBU ), Cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-l, 8-naphthalenediamine,
Pentamethylpiperidin) und Amine, insbesondere tertiäre Amine, (z.B. Triethylamin, Trimethylamin, Tribenzylamin, Triisopropylamin, Tributylamin, Tricyclohexylamin, Triamylamin, Trihexylamin, N,N- Dimethylanilin, Ν,Ν-Dimethyl-toluidin, N,N-Dimethyl-p-aminopyridin, N-Methyl-pyrrolidin, N- Methyl-piperidin, N-Methyl-imidazol, N-Methyl-pyrazol, N-Methyl-morpholin, N-Methyl- hexamethylendiamin, Pyridin, 4-Pyrrolidinopyridin, 4-Dimethylamino-pyridin, Chinolin, α-Picolin, ß- Picolin, Pyrimidin, Acridin, Ν,Ν,Ν',Ν'-Tetramethylendiamin, Ν,Ν,Ν',Ν'-Tetraethylendiamin, Chinoxalin, N-Propyl-diisopropylamin, N-Ethyl-diisopropylamin, N,N'-Dimethyl-cyclohexylamin, 2,6- Lutidin, 2,4-Lutidin oder Triethyldiamin). Pentamethylpiperidine) and amines, especially tertiary amines, (eg triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, Ν, Ν-dimethyl-toluidine, N, N-dimethyl-p-aminopyridine , N-methyl-pyrrolidine, N-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrazole, N-methyl-morpholine, N-methyl-hexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylamino-pyridine, quinoline , α-picoline, β-picoline, pyrimidine, acridine, Ν, Ν, Ν ', Ν'-tetramethylenediamine, Ν, Ν, Ν', Ν'-tetraethylenediamine, quinoxaline, N-propyl-diisopropylamine, N-ethyl-diisopropylamine , N, N'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethyldiamine).
Als saure Reaktionshilfsmittel zur Durchführung der erfindungsgemäßen Verfahren können alle Mineralsäuren (z.B. Halogenwasserstoff-säuren wie Fluorwasserstoffsäure, Chlorwasserstoffsäure, Bromwasserstoffsäure oder Iodwasserstoffsäure sowie Schwefelsäure, Phosphorsäure, Phosphorige Säure, Salpetersäure), Lewis Säuren (z.B. Aluminium(III)-chlorid, Bortrifluorid oder sein Etherat, Titan(IV)chlorid, Zinn(IV)-chlorid) und organische Säuren (z.B. Ameisensäure, Essigsäure, Propionsäure, Malonsäure, Milchsäure, Oxalsäure, Fumarsäure, Adipinsäure, Stearinsäure, Weinsäure, Ölsäure, Methansulfonsäure, Benzoesäure, Benzolsulfonsäure oder para-Toluolsulfonsäure) eingesetzt werden. Die folgenden Herstellungs- und Verwendungsbeispiele illustrieren die Erfindung ohne sie beschränken. As acidic reaction auxiliaries for carrying out the process according to the invention, it is possible to use all mineral acids (eg hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid and sulfuric acid, phosphoric acid, phosphoric acid, nitric acid), Lewis acids (eg aluminum (III) chloride, boron trifluoride or etherate) , Titanium (IV) chloride, tin (IV) chloride) and organic acids (eg formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid ) are used. The following examples of preparation and use illustrate the invention without limiting it.
Herstellungsbeispiele Preparation Examples
Synthesebeispiel 1 Synthetic Example 1
N5-(l-carbamothioylcyclopropyl)-6-chloro-N2-[l-(3, 5-dichloro-2,4-difluoro-phenyl)-2,2,2-trifluoro- ethyl]-l-ethyl-indole-2,5-dicarboxamid (Verbindung Nr. 1-01) N5- (1-carbamothioylcyclopropyl) -6-chloro-N2- [1- (3,5-dichloro-2,4-difluoro-phenyl) -2,2,2-trifluoroethyl] -1-ethyl-indole 2,5-dicarboxamide (Compound No. 1-01)
6-Chlor-l-ethyl-2-({2,2,2-trifluor-l-[3,5-dichlor-2,4-difluorphenyl]ethyl}carbamoyl)-lH-indol-5- carbonsäure (hergestellt nach dem Verfahren gemäß WO-A-2012/119984, vgl. Seite 64, Zeile 16 - Seite 65, Zeile 1 und Seite 66, Zeilen 8-11) (0,523 g, 0,98 mmol) wurde in DMF (9 mL) gelöst. Es wurden nacheinander 1 -Aminocyclopropancarbothioamid (0,150 mg, 0,98 mmol), [Benztriazol-1- yloxy(dimethylamino)methylene]-dimethyl-ammonium hexafluorphosphat (0,374 g, 0,98 mmol) und N- Methylmorpholin (0,200 g, 1,97 mmol) zugesetzt und das Reaktionsgemisch anschließend 15 Stunden bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde mit Ethylacetat versetzt und nacheinander mit Salzsäure (1,0 M) und gesättigter Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet und anschließend das Lösemittel unter vermindertem Druck abdestilliert. Der Rückstand wurde mit Cyclohexan /Essigsäureethylester (60:40) als Laufmittel über Kieselgel chromatographiert und ergab 0,430 g (67 % d.Th.) N5-(l-carbamothioyl-cyclopropyl)-6-chloro-N2-[l -(3,5-dichloro-2,4- difluoro-phenyl)-2,2,2-trifluoro-ethyl]-l-ethyl-indole-2,5-dicarboxamid. HPLC-MS: logP = 4,25; Masse (m/z): 627,0 (M+H)+ 6-Chloro-1-ethyl-2 - ({2,2,2-trifluoro-1- [3,5-dichloro-2,4-difluorophenyl] ethyl} carbamoyl) -H-indole-5-carboxylic acid (prepared according to the method according to WO-A-2012/119984, see page 64, line 16 - page 65, line 1 and page 66, lines 8-11) (0.523 g, 0.98 mmol) was dissolved in DMF (9 mL) , Successively, 1-aminocyclopropanecarbothioamide (0.150 mg, 0.98 mmol), [benztriazol-1-yloxy (dimethylamino) methylene] -dimethyl ammonium hexafluorophosphate (0.374 g, 0.98 mmol) and N-methylmorpholine (0.200 g, 1 , 97 mmol) was added and the reaction mixture then stirred for 15 hours at room temperature. The reaction mixture was added with ethyl acetate and washed successively with hydrochloric acid (1.0 M) and saturated sodium chloride solution, dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel with cyclohexane / ethyl acetate (60:40) as eluent to give 0.430 g (67% of theory) of N5- (1-carbamothioyl-cyclopropyl) -6-chloro-N2- [l (3 , 5-dichloro-2,4-difluoro-phenyl) -2,2,2-trifluoro-ethyl] -l-ethyl-indole-2,5-dicarboxamide. HPLC-MS: log P = 4.25; Mass (m / z): 627.0 (M + H) +
Synthesebeispiel 2 Synthesis Example 2
Die Enantiomerentrennung von Synthesebeispiel 1 (Verbindung Nr. 1-01) wurde durch preparative Normalphasenchromatographie an chiraler stationärer Phase unter folgenden Bedingungen durchgeführt: Säule: CHIRALPAK AS-H 5 μιη- 250 x 4.6 mm; The enantiomer separation of Synthesis Example 1 (Compound No. 1-01) was carried out by preparative normal phase chromatography on a chiral stationary phase under the following conditions: Column: CHIRALPAK AS-H 5 μιη- 250 × 4.6 mm;
Mobile Phase: A= n-Heptan, B=Methanol+Ethanol (1 : 1), A:B=85: 15; Fluss: 0,8 mL/min; 25°C. Mobile phase: A = n-heptane, B = methanol + ethanol (1: 1), A: B = 85:15; Flow: 0.8 mL / min; 25 ° C.
Aus 430 mg N5-(l-carbamothioylcyclopropyl)-6-chloro-N2-[l-(3,5-dichloro-2,4-difluoro-phenyl)-2,2,2- trifluoro-ethyl]-l-ethyl-indole-2,5-dicarboxamid (Synthesebeispiel 1, Verbindung Nr. 1-01) wurden erhalten: 171 mg der Verbindung 1-18, (+)-Enantiomer (Retentionszeit: 7,5 Minuten; ee > 99%, Drehwert: +112,9° ). From 430 mg of N5- (1-carbamothioylcyclopropyl) -6-chloro-N2- [1- (3,5-dichloro-2,4-difluoro-phenyl) -2,2,2-trifluoro-ethyl] -l-ethyl -indole-2,5-dicarboxamide (Synthesis Example 1, Compound No. 1-01) were obtained: 171 mg of compound 1-18, (+) enantiomer (retention time: 7.5 minutes, ee> 99%, rotation: + 112.9 °).
172 g der Verbindung 1-17, (-)-Enantiomer (Retentionszeit: 9,8 Minuten, ee > 99 %,  172 g of compound 1-17, (-) - enantiomer (retention time: 9.8 minutes, ee> 99%,
Drehwert: -103,1° ). Synthesebeispiel 3 Rotation value: -103.1 °). Synthesis Example 3
^5-(l-Carbamothioylcyclopropyl)-6-chlor-l-ethyl-N2-{2,2,2-trifluor-l-[4-fluor-3- (trifluormethyl)phenyl]ethyl}-lH-benzimidazol-2,5-dicarboxamid (Verbindung Nr. 1-30) ^ 5- (1-Carbamothioylcyclopropyl) -6-chloro-1-ethyl-N2- {2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} -H-benzimidazole-2 , 5-dicarboxamide (Compound No. 1-30)
Stufe 1: Ethyl-oxo({2,2,2-trifluor-l-f4-fluor-3-(trifluormethyl)phenylJethyl}amino)acetat Ein Gemisch aus 2,2,2-Trifluor-l-[4-fluor-3-(trifluormethyl)phenyl]ethanamin (15,0 g, 57,4 mmol) und 4-Methylmorpholin (7,58 mL, 68,9 mmol) in Trichlormethan (200 mL) wurde auf 0°C gekühlt, eine Lösung von Oxalsäureethylesterchlorid (8,23 g, 60,3 mmol) in Chloroform (100 mL) langsam zugetropft und anschließend unter Erwärmen auf Raumtemperatur 15 Stunden gerührt. Das Reaktionsgemisch wurde auf Wasser gegossen, zweimal mit 5% iger Natriumhydrogenphosphatlösung extrahiert, die organische Phase über Natriumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck abdestilliert. Man erhielt 20,4 g (99% d. Th.) Ethyl-oxo({2,2,2-trifluor-l-[4-fluor- 3-(trifluormethyl)phenyl]ethyl}amino)acetat, das ohne weitere Reinigung weiter umgesetzt wurde. HPLC-MS: logP = 3,17; Masse (m/z): 362,0 (M+H)+ Step 1: Ethyl oxo ({2,2,2-trifluoro-1-f4-fluoro-3- (trifluoromethyl) phenylethyl} amino) acetate A mixture of 2,2,2-trifluoro-1- (4-fluoro) 3- (trifluoromethyl) phenyl] ethanamine (15.0 g, 57.4 mmol) and 4-methylmorpholine (7.58 mL, 68.9 mmol) in trichloromethane (200 mL) was cooled to 0 ° C, a solution of Ethyl oxalate chloride (8.23 g, 60.3 mmol) in chloroform (100 mL) was slowly added dropwise and then stirred with warming to room temperature for 15 hours. The reaction mixture was poured into water, extracted twice with 5% sodium hydrogen phosphate solution, the organic phase dried over sodium sulfate and the solvent was distilled off under reduced pressure. This gave 20.4 g (99% of theory) of ethyl oxo ({2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} amino) acetate, which without further Cleaning was further implemented. HPLC-MS: log P = 3.17; Mass (m / z): 362.0 (M + H) +
Stufe 2: Oxo({2,2,2-trifluor-l-[ 4-fluor-3-(trifluormethyl)phenyl]ethyl}amino)essigsäure Ethyl-oxo( {2,2,2-trifluor-l-[4-fluor-3-(trifluormethyl)phenyl]ethyl}amino)acetat (20,42 g, 56,0 mmol) wurden in einem Gemisch aus Methanol (200 mL) und Wasser (26 mL) vorgelegt und unter Rühren wurde Natriumhydroxid zugesetzt (8,97 g, 224 mmol). Das Reaktionsgemisch wurde 15 Stunden bei Raumtemperatur gerührt und daraufhin der größte Teil des Lösungsmittel im Vakuum abdestilliert. Der Rückstand wurde in Wasser /Tertiärbutylmethylether aufgenommen, die Phasen getrennt und die wässrige Phase zweimal mit Tertiärbutylmethylether extrahiert. Die wässrige Phase wurde anschließend mit 10%oiger Salzsäure bis pH3 angesäuert und mehrfach mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit gesättigter Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel im Vakuum abdestilliert. Man erhielt 19,55 g (85% d. Th.) Oxo({2,2,2-trifluor-l-[4-fluor-3-(trifluormethyl)phenyl]ethyl}amino)essigsäure, das ohne weitere Reinigung weiter umgesetzt wurde. HPLC-MS: logP = 1,84; Masse (m/z): 332,0 (M+H)+ Stufe 3a: Ethyl-5-amino-2-chlor-4-(ethylamino)benzoat Step 2: Oxo ({2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} amino) acetic acid ethyl-oxo ({2,2,2-trifluoro-l- [4 fluoro-3- (trifluoromethyl) phenyl] ethyl} amino) acetate (20.42 g, 56.0 mmol) were initially charged in a mixture of methanol (200 mL) and water (26 mL) and sodium hydroxide added with stirring ( 8.97 g, 224 mmol). The reaction mixture was stirred for 15 hours at room temperature and then distilled off most of the solvent in vacuo. The residue was taken up in water / tert-butyl methyl ether, the phases were separated and the aqueous phase was extracted twice with tert-butyl methyl ether. The aqueous phase was then acidified to pH3 with 10% hydrochloric acid and extracted several times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulfate and the solvent was distilled off in vacuo. This gave 19.55 g (85% of theory) of oxo ({2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} amino) acetic acid, which continued without further purification was implemented. HPLC-MS: log P = 1.84; Mass (m / z): 332.0 (M + H) + Step 3a: Ethyl 5-amino-2-chloro-4- (ethylamino) benzoate
Ethyl-2-chlor-4-(ethylamino)-5-nitrobenzoat: Ethyl-2-chlor-4-fluor-5-nitrobenzoat (3,60g, 14,5 mmol) wurde in THF (28 mL) vorgelegt und mit einer 2M Ethylamin Lösung in THF (14,5 mL, 29 mmol) versetzt. Anschließend wir 15 Stunden bei Raumtemperatur gerührt. Zur Aufarbeitung wird das Reaktionsgemisch auf Wasser gegeben und zweimal mit Ethylacetat extrahiert. Die vereinigten organischen Phasen werden mit Wasser und mit 5% iger Natriumhydrogenphosphatlösung gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel unter vermindertem Druck abdestilliert. Der Rückstand wird über Kieselgel mit Cyclohexan/Essigester chromatographiert wobei 2,80 g (71,3 % d. Th.) Ethyl-2-chlor-4-(ethylamino)-5-nitrobenzoat erhalten wurden. HPLC-MS: logP = 3,49; Masse (m/z): 273,0 (M+H)+ Ethyl 2-chloro-4- (ethylamino) -5-nitrobenzoate: Ethyl 2-chloro-4-fluoro-5-nitrobenzoate (3.60 g, 14.5 mmol) was initially charged in THF (28 mL) and washed with a 2M ethylamine solution in THF (14.5 mL, 29 mmol). Then we stirred for 15 hours at room temperature. For workup, the reaction mixture is added to water and extracted twice with ethyl acetate. The combined organic phases are washed with water and with 5% sodium hydrogen phosphate solution, dried over sodium sulfate and the solvent is distilled off under reduced pressure. The residue is chromatographed on silica gel with cyclohexane / ethyl acetate to give 2.80 g (71.3% of theory) of ethyl 2-chloro-4- (ethylamino) -5-nitrobenzoate. HPLC-MS: logP = 3.49; Mass (m / z): 273.0 (M + H) +
Ethyl-5-amino-2-chlor-4-(ethylamino)benzoat: Ethyl-2-chlor-4-(ethylamino)-5-nitrobenzoat (2,47 g, 9,05 mmol) wurde in Ethanol (86 mL) / Wasser (14 mL) vorgelegt und mit Ammoniumchlorid (775,2 mg, 14,4 mmol) versetzt. Das Reaktionsgemisch wurde auf 60 °C erwärmt , Eisenpulver (5,06 g, 90,5 mmol) zugegeben und anschließend 3 Stunden bei Rückflußtemperatur gerührt. Nach Abkühlen wurde über Kieselgur filtriert, mehrfach mit Ethanol nachgewaschen und das Lösungsmittel unter vermindertem Druck abdestilliert. Der Rückstand wurde in Ethylacetat aufgenommen, die Lösung mit Wasser und mit gesättigter Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel abdestiliert. Man erhielt 2,16 g (83 % d. Th.) Ethyl-5-amino-2-chlor-4- (ethylamino)benzoat . HPLC-MS: logP = 2,31 ; Masse (m/z): 243,0 (M+H)+ Stufe 3: Ethyl-2-chlor-4-(ethylamino)-5-{[oxo({2,2,2-trifluor-l-[ 4-fluor-3-(trifluormethyl)phenyl] ethyl}amino)acetyl]amino}benzoat Ethyl 5-amino-2-chloro-4- (ethylamino) benzoate: ethyl 2-chloro-4- (ethylamino) -5-nitrobenzoate (2.47 g, 9.05 mmol) was dissolved in ethanol (86 mL). / Water (14 mL) and treated with ammonium chloride (775.2 mg, 14.4 mmol). The reaction mixture was heated to 60 ° C, iron powder (5.06 g, 90.5 mmol) was added and then stirred at reflux temperature for 3 hours. After cooling, it was filtered through kieselguhr, washed several times with ethanol, and the solvent was distilled off under reduced pressure. The residue was taken up in ethyl acetate, the solution was washed with water and with saturated sodium chloride solution, dried over sodium sulfate and the solvent was distilled off. 2.16 g (83% of theory) of ethyl 5-amino-2-chloro-4- (ethylamino) benzoate were obtained. HPLC-MS: logP = 2.31; Mass (m / z): 243.0 (M + H) + Step 3: Ethyl 2-chloro-4- (ethylamino) -5 - {[oxo ({2,2,2-trifluoro-l- [4 fluoro-3- (trifluoromethyl) phenyl] ethyl} amino) acetyl] amino} benzoate
Oxo({2,2,2-trifluor-l-[4-fluor-3-(trifluormethyl)phenyl]ethyl}amino)essigsäure (2,30 g, 6,90 mmol) wurde in Trichlormethan (50 mL) gelöst, mit Thionylchlorid (2,05 g, 17,2 mmol) sowie 2 Tropfen DMF versetzt und 15 Stunden bei 50 °C gerührt. Das Lösungsmittel wurde im Vakkum addestilliert, der Rückstand in wenig Trichlormethan aufgenommen und zu einer Lösung von Ethyl-5-amino-2-chlor-4- (ethylamino)benzoat (2,16 g, 7,59 mmol) aus Stufe 3a und Triethylamin (2,4 mL, 17,2 mmol) in Trichlormethan (25 mL) getropft. Nach 48 Stunden Rühren bei Raumtemperatur wurde der größte Teil des Lösungsmittel im Vakuum abdestilliert und der Rückstand in Wasser /Ethylacetat aufgenommen. Die Phasen wurden getrennt und die wässrige Phase zweimal mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit 5% iger Natriumhydrogenphosphatlösung gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel im Vakuum abdestilliert. Man erhielt 4,5 g (54% d. Th.) Ethyl-2-chlor-4-(ethylamino)-5- {[oxo({2,2,2-trifluor-l-[4-fluor-3-(trifluormethyl)phenyl] ethyl}amino)acetyl]amino}benzoat, das ohne Reinigung weiter umgesetzt wurde. HPLC-MS: logP = 4,36; Masse (m/z): 558,0 (M+H)+ Stufe 4: Ethyl-6-chlor-l-ethyl-2-({2,2,2-trifluor-l-[4-fluor-3-(trifluormethyl)phenyl] Oxo ({2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} amino) acetic acid (2.30 g, 6.90 mmol) was dissolved in trichloromethane (50 mL), with thionyl chloride (2.05 g, 17.2 mmol) and 2 drops of DMF and stirred at 50 ° C for 15 hours. The solvent was distilled off in vacuo, the residue taken up in a little trichloromethane and added to a solution of ethyl 5-amino-2-chloro-4- (ethylamino) benzoate (2.16 g, 7.59 mmol) from step 3a and triethylamine (2.4 mL, 17.2 mmol) in trichloromethane (25 mL). After 48 hours of stirring at room temperature, most of the solvent was distilled off in vacuo and the residue taken up in water / ethyl acetate. The phases were separated and the aqueous phase extracted twice with ethyl acetate. The combined organic phases were washed with 5% sodium hydrogen phosphate solution, dried over sodium sulfate and the solvent was distilled off in vacuo. 4.5 g (54% of theory) of ethyl 2-chloro-4- (ethylamino) -5-{[oxo ({2,2,2-trifluoro-l- [4-fluoro-3-one]) were obtained. (trifluoromethyl) phenyl] ethyl} amino) acetyl] amino} benzoate, which was further reacted without purification. HPLC-MS: log P = 4.36; Mass (m / z): 558.0 (M + H) + Step 4: Ethyl 6-chloro-1-ethyl-2 - ({2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) phenyl]
lH-benzimidazol-5-carboxylat lH-benzimidazole-5-carboxylate
Ethyl-2-chlor-4-(ethylamino)-5- {[oxo({2,2,2-trifluor-l -[4-fluor-3-(trifluormethyl)phenyl^ Ethyl 2-chloro-4- (ethylamino) -5- {[oxo ({2,2,2-trifluoro-l - [4-fluoro-3- (trifluoromethyl) phenyl]
ethyl}amino)acetyl]amino}benzoat (4,50 g, 8,06 mmol) wurde in Toluol (90 mL) gelöst, mit p- Toluolsulfonsäure Monohdrat (0,30 g, 1,61 mmol) und 15 Stunden bei Rückflußtemperatur am Wasserabscheider gerührt. Nach Abkühlen wurde mit gesättigter Natriumhydrogencarbonatlösung gewaschen, über Natriumsulfat getrocknet und das Lösungsmittel im Vakkum addestilliert. Der Rückstand wurde mit Cyclohexan/Essigsäureethylester (80:20) als Laufmittel über Kieselgel chromatographiert Man erhielt 0,99 g (20% d. Th.) Ethyl-6-chlor-l-ethyl-2-({2,2,2-trifluor-l-[4-fluor- 3-(trifluormethyl)phenyl]ethyl}carbamoyl)-lH-benzimidazol-5-carboxylat. HPLC-MS: logP = 5,03; Masse (m/z): 541,0 (M+H)+ 'HNMR (D3-DMSO): δ 1.33 (t, 3H), 1.37 (t, 3H), 4.37 (q, 2H), 4.60 (q, 2H), 6.36 (m, 1H), 7.64 (m, 1H), 7.69 (s, 1H), 8.21 (m, 2H), 8.42 (m, 1H), 8.62 (s, 1H). ethyl} amino) acetyl] amino} benzoate (4.50 g, 8.06 mmol) was dissolved in toluene (90 mL), with p-toluenesulfonic acid monohydrate (0.30 g, 1.61 mmol) and refluxed for 15 hours stirred on a water separator. After cooling, the mixture was washed with saturated sodium bicarbonate solution, dried over sodium sulfate and the solvent was distilled off in vacuo. The residue was chromatographed on silica gel with cyclohexane / ethyl acetate (80:20) as eluent to give 0.99 g (20% of theory) of ethyl 6-chloro-1-ethyl-2 - ({2,2,2 trifluoro-1- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} carbamoyl) -1H-benzimidazole-5-carboxylate. HPLC-MS: log P = 5.03; Mass (m / z): 541.0 (M + H) + HNMR (D 3 -DMSO): δ 1.33 (t, 3H), 1.37 (t, 3H), 4.37 (q, 2H), 4.60 (q , 2H), 6.36 (m, 1H), 7.64 (m, 1H), 7.69 (s, 1H), 8.21 (m, 2H), 8.42 (m, 1H), 8.62 (s, 1H).
Stufe 5: 6-chlor-l-ethyl-2-({2,2,2-trifluor-l-[4-fluor-3-(trifluormethyl)phenylJethyl}carbamoyl)-lH- benzimidazol- 5 -carbonsäure Ethyl-6-chlor- 1 -ethyl-2-( {2,2,2-trifluor- 1 -[4-fluor-3-(trifluormethyl)phenyl]ethyl} carbamoyl)- 1 H- benzimidazol-5-carboxylat (0,495 g, 0,81 mmol) wurde in Dioxan (25 mL) / Wasser (2,8 mL) vorgelegt und mit Litiumhydroxid (58,3 mg, 2,43 mmol) versetzt. Das Reaktionsgemisch wurde 48 h h bei Raumtemperatur nachgerührt woraufhin das Lösungsmittel im Vakuum abdestilliert wurde. Der Rückstand wurde in Wasser aufgenommen und mit konzentrierter Salzsäure auf pH 1 gebracht. Der ausgefallene Niederschlag wurde ab filtriert und getrocknet. Man erhielt 366 mg (83 % d.Th.) 6-Chlor- l-ethyl-2-({2,2,2-trifluor-l-[3-(trifluormethyl)phenyl]ethyl}carbamoyl)-lH-indol-5-carbonsäure. Step 5: 6-Chloro-1-ethyl-2 - ({2,2,2-trifluoro-1- [4-fluoro-3- (trifluoromethyl) -phenyl-ethyl} -carbamoyl) -lH-benzimidazole-5-carboxylic acid ethyl-6 -chloro-1-ethyl-2- ({2,2,2-trifluoro-1 - [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} carbamoyl) -1 H -benzimidazole-5-carboxylate (0.495 g, 0.81 mmol) was initially charged in dioxane (25 mL) / water (2.8 mL) and lithium hydroxide (58.3 mg, 2.43 mmol) was added. The reaction mixture was stirred for 48 h at room temperature, whereupon the solvent was distilled off in vacuo. The residue was taken up in water and brought to pH 1 with concentrated hydrochloric acid. The precipitate was filtered off and dried. 366 mg (83% of theory) of 6-chloro-1-ethyl-2 - ({2,2,2-trifluoro-1- [3- (trifluoromethyl) phenyl] ethyl} carbamoyl) -H-indole were obtained -5-carboxylic acid.
HPLC-MS: logP = 3,66; Masse (m/z): 512,1 (M+H)+ 'HNMR (D3-DMSO): δ 1.31 (t, 3H), 4.60 (q, 2H), 6.30 (m, 1H), 7.64 (m, 1H), 8,06 (s, 1H), 8.2-8.3 (m, 3H), 8.43 (m, 1H). HPLC-MS: logP = 3.66; Mass (m / z): 512.1 (M + H) + HNMR (D3-DMSO): δ 1.31 (t, 3H), 4.60 (q, 2H), 6.30 (m, 1H), 7.64 (m, 1H), 8.06 (s, 1H), 8.2-8.3 (m, 3H), 8.43 (m, 1H).
Stufe 6: 'N5-(l-Carbamothioylcyclopropyl)-6-chlor-l-ethyl-N2-{2,2,2-trifluor-l-[ 4-fluor-3- (trifluormethyl)phenyl]ethyl}-lH-benzimidazol-2,5-dicarboxamid (Verbindung Nr. 1-30) Step 6: 'N5- (l-Carbamothioylcyclopropyl) -6-chloro-l-ethyl-N2- {2,2,2-trifluoro-l- [4-fluoro-3- (trifluoromethyl) phenyl] ethyl} -lH- benzimidazole-2,5-dicarboxamide (Compound No. 1-30)
6-Chlor- 1 -ethyl-2-( {2,2,2-trifluor- 1 -[3-(trifluormethyl)phenyl]ethyl} carbamoyl)- 1 H-indol-5- carbonsäure (200 mg, 0,37 mmol) wurde in DMF (2 mL) gelöst. Es wurden nacheinander 1- Aminocyclopropancarbothioamid (62,2 mg, 0,40 mmol), [Benztriazol-1- yloxy(dimethylamino)methylene]-dimethyl-ammonium hexafluorphosphat (154 mg, 0,40 mmol) und N- Methylmorpholin (112 mg, 1,11 mmol) zugesetzt und anschließend 15 Stunden bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde auf Wasser gegossen und mit Ethylacetat extrahiert. Nach Wasschen mit gesättigter Natriumchloridlösung wurde über Magnesiumsulfat getrocknet und anschließend das Lösemittel unter vermindertem Druck abdestilliert. Der Rückstand wurde mit Cyclohexan /Essigsäureethylester (60:40) als Laufmittel über Kieselgel chromatographiert und ergab 0,139 g (54 % d.Th.) m-(l-Carbamothioylcyclopropyl)-6-chlor-l-ethyl-N2-{2,2,2-trifluo 6-Chloro-1-ethyl-2- ({2,2,2-trifluoro-1 - [3- (trifluoromethyl) phenyl] ethyl} carbamoyl) -1H-indole-5-carboxylic acid (200mg, 0.37 mmol) was dissolved in DMF (2 mL). Successively 1-aminocyclopropanecarbothioamide (62.2 mg, 0.40 mmol), [benztriazol-1-yloxy (dimethylamino) methylene] -dimethyl ammonium hexafluorophosphate (154 mg, 0.40 mmol) and N-methylmorpholine (112 mg , 1.11 mmol) was added and then stirred for 15 hours at room temperature. The reaction mixture was poured onto water and extracted with ethyl acetate. After washing with saturated sodium chloride solution was dried over magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel with cyclohexane / ethyl acetate (60:40) as eluent to give 0.139 g (54% of theory) of m- (1-carbamothioylcyclopropyl) -6-chloro-1-ethyl-N 2 - {2,2,2-trifluoro
3-(trifluormethyl)phenyl]ethyl}-lH-benzimidazol-2,5-dicarboxamid . HPLC-MS: logP = 3,56; Masse (m/z): 609,9 (M+H)+. 3- (trifluoromethyl) phenyl] ethyl} -1H-benzimidazole-2,5-dicarboxamide. HPLC-MS: log P = 3.56; Mass (m / z): 609.9 (M + H) + .
Die in der folgenden Tabelle 1 beschriebenen erfindungsgemäßen Verbindungen der Formel (I) sind ebenfalls bevorzugte erfindungsgemäße Verbindungen, die man gemäß oder analog zu den oben beschriebenen Synthesebeispielen erhält. The compounds of the formula (I) according to the invention which are described in the following Table 1 are likewise preferred compounds according to the invention which are obtained according to or analogously to the synthesis examples described above.
Tabelle 1 Table 1
Nr. (R')n R2 R1 R G R6 (M+H)+ a) lOR P "Nr (R ') n R 2 R 1 RGR 6 (M + H) + a) lOR P "
1-01 2,4-F2; 3,5-Cl. F H Et CH Cl 627,0 4,251-01 2,4-F 2 ; 3,5-Cl. FH Et CH CI 627.0 4.25
1-02 3,5-Cl2;4-F F H Et CH Cl 610,0 4,041-02 3,5-Cl 2 ; 4-FFH Et CH Cl 610,0 4.04
1-03 3-CF3;4-F F H Et CH Cl 609,1 3,701-03 3-CF 3 ; 4-FFH Et CH Cl 609.1 3.70
1-04 3-Cl;4-F F H Et CH Cl 575,1 3,571-04 3-Cl; 4-F F H Et Cl Cl 575.1 3.57
1-05 3,4,5-Cl3 F H Et CH Cl 625,0 4,331-05 3,4,5-Cl 3 FH Et CH Cl 625,0 4,33
1-06 3-Br;4-F F H Et CH Cl 619,0 3,641-06 3-Br; 4-F F H Et CH Cl 619.0 3.64
1-07 3-CF3;4-Cl F H Et CH Cl 625,1 3,961-07 3-CF 3 ; 4-Cl FH Et CH Cl 625.1 3.96
1-08 2,4-F2; 3,5-Cl2 F H Me CH Cl 613,0 3,941-08 2,4-F 2 ; 3,5-Cl 2 FH Me CH Cl 613.0 3.94
1-09 3,4-Cl2;5-F F H Et CH Cl 610,0 4,021-09 3,4-Cl 2 ; 5-FFH Et CH Cl 610,0 4.02
1-10 3-F;5-CF3 F H Et CH Cl 609,0 3,811-10 3-F; 5-CF 3 FH Et CH Cl 609.0 3.81
1-11 2-F;3-Cl F H Et CH Cl 575,1 3,691-11 2-F; 3-Cl F H Et CH Cl 575.1 3.69
1-12 2,4-F2; 3,5-Cl2 F H Prop-2-in-l-yl CH Cl 637,1 3,941-12 2,4-F 2 ; 3,5-Cl 2 FH Prop-2-yn-1-yl CH Cl 637.1 3.94
1-13 3-CF3;4-Cl F H Et CH Me 605,0 3,891-13 3-CF 3 ; 4-Cl FH Et CH Me 605.0 3.89
1-14 3,5-Cl2;4-F F H Prop-2-in-l-yl CH Cl 618,9 3,811-14 3,5-Cl 2 ; 4-FFH Prop-2-yn-1-yl CH Cl 618.9 3.81
1-15 3,5-Cl2;4-F F H Me CH Cl 595,0 3,761-15 3,5-Cl 2 ; 4-FFH Me CH Cl 595.0 3.76
1-16 3-CF3;4-Cl F H Me CH Cl 611,1 3,70 Nr. (R')n R2 R3 R4 G Ii'1 ( +H)+ a> log p■> 1-16 3-CF 3 ; 4-Cl FH Me CH Cl 611.1 3.70 Nr (R ') n R 2 R 3 R 4 G Ii' 1 (+ H) + a > log p ■ >
4,27; 4.27;
1-17 2,4-F2; 3,5-Cl2 F H Et CH Cl 627,0 (-)-Enantiomer 1-17 2,4-F 2 ; 3,5-Cl 2 FH Et CH Cl 627,0 (-) Enantiomer
4,27;4.27;
1-18 2,4-F2; 3,5-C12 F H Et CH Cl 627,0 (+)-Enantiomer 1-18 2,4-F2; 3,5-C12 F H Et CH Cl 627,0 (+) enantiomer
1-19 3-CF3;4-Cl F H Prop-2-in-l-yl CH Cl 635,1 3,73 1-19 3-CF 3 ; 4-Cl FH Prop-2-yn-1-yl CH Cl 635.1 3.73
1-20 3,4,5-Cl3 F H Me CH Cl 612,0 4,07 1-20 3,4,5-Cl 3 FH Me CH Cl 612,0 4.07
1-21 3,4,5-Cl3 F H Prop-2-in-l-yl CH Cl 636,0 4,09 1-21 3,4,5-Cl 3 FH Prop-2-yn-1-yl CH Cl 636.0 4.09
1-22 3-Cl;5-CF3 F H Et CH Cl 625,0 4,11 1-22 3-Cl; 5-CF 3 FH Et CH Cl 625.0 4.11
1-23 3,5-F2 H H Et CH Cl 541,0 3,07 1-23 3,5-F 2 HH Et CH Cl 541.0 3.07
1-24 3,5-Cl2 H H Et CH Cl 573,9 3,65 1-24 3,5-Cl 2 HH Et CH Cl 573.9 3.65
1-25 3,4-Cl2 H H Et CH Cl 573,9 3,54 1-25 3,4-Cl 2 HH Et CH Cl 573.9 3.54
1-26 2,3,4-F3;5-Cl F H Et CH Cl 612,1 3,99 1-26 2,3,4-F 3 ; 5-Cl FH Et CH Cl 612,1 3,99
1-27 2,5-F2;3,4-Cl2 F H Et CH Cl 628,1 4,28 1-27 2,5-F 2 ; 3,4-Cl 2 FH Et CH Cl 628.1 4.28
1-28 2,4-F2;3,5-Cl2 H H Et CH Cl 610,1 3,90 1-28 2,4-F 2 ; 3,5-Cl 2 HH Et CH Cl 610,1 3,90
1-29 2,3-F2;4,5-Cl2 F H Et CH Cl 628,1 4,27 1-29 2,3-F 2 ; 4,5-Cl 2 FH Et CH Cl 628.1 4.27
1-30 3-CF3;4-F F H Et N Cl 609,9 3,46 1-30 3-CF 3 ; 4-FFH Et N Cl 609.9 3.46
1-31 2,3,5-F3;4-Cl F H Et CH Cl 612,3 4,02 1-31 2,3,5-F 3 ; 4-Cl FH Et CH Cl 612.3 4.02
1-32 3-CF3;4-F H H Et CH Cl 591,1 3,41 1-32 3-CF 3 ; 4-FHH Et CH Cl 591.1 3.41
Abkürzungen: Et = Ethyl, Me = Methyl; Ή-NMR Daten Abbreviations: Et = ethyl, Me = methyl; Ή-NMR data
Beispiel 1-01: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-01: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,775 (7,0); 9,751 (4,4); 8,874 (9,1); 8,768 (3,4); 8,281 (2,3); 8,262 (4,2); 8,244 (2,2); 8,125 (15,4); 7,817 (11,1); 7,406 (11 ,0); 6,397 (0,4); 6,376 (1 ,6); 6,355 (2,3); 6,333 (1 ,7); 6,312 (0,5); 4,544 (1 J)\ 4,527 (4,9); 4,509 (4,8); 4,491 (1 ,6); 3,323 (111 ,7); 2,680 (0,6); 2,676 (1 ,2); 2,671 (1 ,6); 2,667 (1 ,2); 2,662 (0,5); 2,525 (5,4); 2,511 (92,8); 2,507 (182,2); 2,502 (236,5); 2,498 (169,4); 2,493 (80,0); 2,338 (0,6); 2,333 (1,2); 2,329 (1,6); 2,324 (1,1); 2,320 (0,5); 1,858 (3,2); 1,848 (7,1); 1,838 (7,7); 1,829 (3,1); 1,398(4,8); 1,336 (0,8); 1,273 (3,5); 1,263 (7,6); 1,253 (7,8); 1,243 (3,7); δ = 9.775 (7.0); 9,751 (4.4); 8,874 (9.1); 8,768 (3,4); 8,281 (2,3); 8,262 (4,2); 8.244 (2.2); 8.125 (15.4); 7,817 (11,1); 7,406 (11, 0); 6,397 (0.4); 6,376 (1,6); 6.355 (2.3); 6,333 (1, 7); 6.312 (0.5); 4,544 (1 J) \ 4.527 (4.9); 4,509 (4,8); 4,491 (1,6); 3,323 (111, 7); 2,680 (0.6); 2,676 (1, 2); 2,671 (1,6); 2,667 (1, 2); 2,662 (0.5); 2,525 (5.4); 2,511 (92.8); 2,507 (182,2); 2,502 (236.5); 2,498 (169.4); 2,493 (80.0); 2.338 (0.6); 2.333 (1.2); 2,329 (1.6); 2.324 (1.1); 2.320 (0.5); 1,858 (3.2); 1,848 (7.1); 1,838 (7.7); 1,829 (3,1); 1,398 (4.8); 1,336 (0.8); 1,273 (3.5); 1,263 (7.6); 1,253 (7,8); 1,243 (3.7);
1.233 (7,8); 1,216 (16,0); 1,198 (7,2); 0,146 (0,5); 0,008 (4,7); 0,000 (125,9); -0,009 (4,0); -0,150 (0,5) 1,233 (7.8); 1,216 (16,0); 1,198 (7.2); 0.146 (0.5); 0.008 (4.7); 0.000 (125.9); -0.009 (4.0); -0.150 (0.5)
Beispiel I-02: 1H-NMR (400,0 MHz, d6-DMSO): Example I-02: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,771 (2,7); 9,635 (3,4); 9,611 (3,5); 8,871 (7,9); 8,771 (2,7); 8,120 (16,0); 8,115 (10,4); 8,099 (9,8); 7,853 (0,4); 7,806 (9,5); 7,399 (0,4); 7,381 (9,1); 6,323 (0,4); 6,302 (1,3); 6,280 (1,9); 6,258 (1,4); 6,236 (0,4); 4,543 (1,5); 4,526 δ = 9.771 (2.7); 9,635 (3,4); 9,611 (3.5); 8,871 (7.9); 8,771 (2.7); 8.120 (16.0); 8,115 (10.4); 8.099 (9.8); 7,853 (0.4); 7.806 (9.5); 7,399 (0.4); 7,381 (9.1); 6,323 (0.4); 6,302 (1,3); 6.280 (1.9); 6.258 (1.4); 6.236 (0.4); 4,543 (1.5); 4,526
(4.2) ; 4,508 (4,2); 4,491 (1,4); 3,790 (0,4); 3,752 (0,3); 3,324 (55,1); 2,680 (0,5); 2,676 (1,1); 2,671 (1,6); 2,667 (1,1); 2,662 (0,5); 2,541 (0,7); 2,525 (5,3); 2,520 (8,1); 2,511 (88,9); 2,507 (178,4); 2,502 (234,2); 2,498 (165,5); 2,493 (76,8); 2,338 (0,5); 2,333 (1,1); 2,329 (1,6); 2,324 (1,1); 2,320 (0,5); 2,075 (0,4); 1,858 (2,7); 1,847 (5,8); 1,838 (6,2); 1,829(4.2); 4,508 (4,2); 4.491 (1.4); 3,790 (0.4); 3,752 (0.3); 3,324 (55.1); 2,680 (0.5); 2,676 (1.1); 2,671 (1.6); 2,667 (1,1); 2,662 (0.5); 2,541 (0.7); 2,525 (5.3); 2,520 (8,1); 2,511 (88.9); 2,507 (178.4); 2,502 (234,2); 2,498 (165.5); 2,493 (76.8); 2.338 (0.5); 2.333 (1.1); 2,329 (1.6); 2.324 (1.1); 2.320 (0.5); 2.075 (0.4); 1,858 (2.7); 1,847 (5.8); 1,838 (6.2); 1,829
(2.5) ; 1,273 (2,9); 1,263 (6,2); 1,253 (6,3); 1,243 (2,9); 1,231 (6,6); 1,214 (13,9); 1,196 (6,2); 0,146 (0,5); 0,008 (4,2);(2.5); 1,273 (2.9); 1,263 (6.2); 1,253 (6.3); 1,243 (2.9); 1,231 (6,6); 1,214 (13.9); 1.196 (6.2); 0.146 (0.5); 0.008 (4.2);
0,000 (127,6); -0,009 (3,9); -0,150 (0,5) 0,000 (127.6); -0.009 (3.9); -0.150 (0.5)
Beispiel I-03: 1H-NMR (400,0 MHz, d6-DMSO): Example I-03: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,765 (7,0); 9,741 (4,3); 8,868 (9,0); 8,772 (3,2); 8,316 (1,0); 8,296 (2,7); 8,283 (2,6); 8,182 (1,4); 8,177 (1,4); 8,171 δ = 9.765 (7.0); 9,741 (4,3); 8,868 (9.0); 8,772 (3.2); 8.316 (1.0); 8.296 (2.7); 8.283 (2.6); 8,182 (1.4); 8.177 (1.4); 8,171
(1.6) ; 8,162 (1,8); 8,155 (1,6); 8,149 (1,6); 8,117 (16,0); 7,802 (11,1); 7,688 (2,5); 7,662 (3,1); 7,639 (2,3); 7,370 (10,9); 6,388 (0,4); 6,366 (1,5); 6,344 (2,2); 6,322 (1,6); 6,300 (0,5); 4,542 (1,6); 4,525 (4,6); 4,507 (4,5); 4,489 (1,6); 3,326 (203,7); 3,303 (0,5); 2,681 (0,5); 2,676 (1,0); 2,672 (1,4); 2,667 (1,0); 2,663 (0,5); 2,525 (4,1); 2,520 (6,5); 2,512 (76,5); 2,507 (151,9); 2,503 (198,0); 2,498 (140,5); 2,493 (65,2); 2,338 (0,4); 2,334 (1,0); 2,329 (1,3); 2,325 (0,9); 2,320 (0,4); 2,075 (6,0); 1,858 (3,1); 1,848 (6,9); 1,839 (7,5); 1,829 (3,0); 1,272 (3,2); 1,262 (7,5); 1,253 (7,2); 1,243 (2,9); 1,224(1.6); 8,162 (1.8); 8.155 (1.6); 8.149 (1.6); 8.117 (16.0); 7,802 (11,1); 7,688 (2.5); 7,662 (3,1); 7.639 (2.3); 7,370 (10.9); 6,388 (0.4); 6.366 (1.5); 6,344 (2,2); 6.332 (1.6); 6,300 (0.5); 4,542 (1.6); 4,525 (4,6); 4,507 (4,5); 4.489 (1.6); 3,326 (203,7); 3.303 (0.5); 2,681 (0.5); 2,676 (1.0); 2,672 (1.4); 2,667 (1.0); 2,663 (0.5); 2,525 (4.1); 2,520 (6.5); 2,512 (76.5); 2,507 (151.9); 2,503 (198.0); 2,498 (140.5); 2,493 (65.2); 2.338 (0.4); 2.334 (1.0); 2,329 (1,3); 2.325 (0.9); 2.320 (0.4); 2.075 (6.0); 1,858 (3,1); 1,848 (6.9); 1,839 (7.5); 1,829 (3.0); 1,272 (3,2); 1,262 (7.5); 1,253 (7.2); 1,243 (2.9); 1,224
(7.3) ; 1,207 (15,9); 1 ,189 (7,0); 0,146 (0,4); 0,008 (3,2); 0,000 (92,3); -0,009 (2,7); -0,150 (0,4) (7.3); 1,207 (15,9); 1, 189 (7: 0); 0.146 (0.4); 0.008 (3.2); 0,000 (92.3); -0.009 (2.7); -0.150 (0.4)
Beispiel I-04: 1H-NMR (400,0 MHz, d6-DMSO): Example I-04: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,768 (2,4); 9,666 (3,0); 9,642 (3,1); 8,868 (6,8); 8,776 (2,4); 8,111 (12,3); 8,088 (2,3); 8,083 (2,5); 8,070 (2,4); 8,065 (2,3); 7,801 (9,4); 7,790 (1,7); 7,784 (1,5); 7,778 (1,4); 7,772 (1,3); 7,568 (3,3); 7,545 (4,8); 7,523 (2,8); 7,375 (8,1); δ = 9.768 (2.4); 9,666 (3.0); 9,642 (3,1); 8,868 (6.8); 8.776 (2.4); 8,111 (12.3); 8.088 (2.3); 8,083 (2.5); 8.070 (2.4); 8.065 (2.3); 7,801 (9.4); 7,790 (1.7); 7.784 (1.5); 7,778 (1.4); 7,772 (1.3); 7,568 (3.3); 7,545 (4,8); 7,523 (2,8); 7,375 (8,1);
6.234 (1,2); 6,212 (1,7); 6,189 (1,2); 6,167 (0,4); 4,545 (1,3); 4,528 (3,6); 4,510 (3,6); 4,492 (1,2); 3,329 (11,0); 2,676 (0,6); 2,671 (0,9); 2,667 (0,6); 2,525 (3,3); 2,520 (5,3); 2,511 (51,0); 2,507 (101,2); 2,502 (132,5); 2,498 (94,4); 2,493 (44,4); 2,334 (0,6); 2,329 (0,9); 2,324 (0,6); 2,076 (16,0); 1,858 (2,4); 1,847 (5,2); 1,838 (5,7); 1,829 (2,3); 1,273 (2,5); 1,263 (5,6); 1,254 (5,6); 1,243 (2,4); 1,227 (5,7); 1,209 (12,2); 1,191 (5,4); 0,008 (2,6); 0,000 (70,2); -0,009 (2,2) Beispiel I-05: 1H-NMR (400,0 MHz, d6-DMSO): 6,234 (1,2); 6.212 (1.7); 6,189 (1,2); 6.167 (0.4); 4,545 (1.3); 4,528 (3.6); 4,510 (3.6); 4,492 (1,2); 3,329 (11.0); 2,676 (0.6); 2,671 (0.9); 2,667 (0.6); 2,525 (3.3); 2,520 (5.3); 2,511 (51.0); 2,507 (101,2); 2,502 (132.5); 2,498 (94.4); 2,493 (44.4); 2.334 (0.6); 2,329 (0.9); 2.324 (0.6); 2.076 (16.0); 1,858 (2,4); 1,847 (5.2); 1,838 (5.7); 1.829 (2.3); 1,273 (2.5); 1,263 (5.6); 1.254 (5.6); 1,243 (2,4); 1,227 (5.7); 1,209 (12,2); 1,191 (5.4); 0.008 (2.6); 0,000 (70.2); -0.009 (2.2) Example I-05: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,769 (2,3); 9,661 (2,5); 9,637 (2,6); 8,872 (5,6); 8,772 (2,2); 8,150 (16,0); 8,121 (9,0); 7,806 (7,1); 7,383 (6,9); 6,319 (1,0); 6,297 (1,5); 6,274 (1,1); 6,253 (0,3); 4,542 (1,2); 4,525 (3,4); 4,507 (3,4); 4,490 (1,1); 3,325 (179,5); 2,676 (1,0); 2,672 (1,5); 2,667 (1,1); 2,525 (7,4); 2,511 (88,9); 2,507 (176,0); 2,502 (231,2); 2,498 (170,2); 2,494 (85,7); 2,334 (1,2); 2,329 (1,6); 2,325 (1,2); 2,075 (0,8); 1,858 (2,1); 1,847(4,6); 1,838 (5,0); 1,829 (2,1); 1,355(1,7); 1,273 (2,6); 1,263 δ = 9.769 (2.3); 9,661 (2.5); 9.637 (2.6); 8,872 (5.6); 8.772 (2.2); 8,150 (16.0); 8,121 (9,0); 7,806 (7.1); 7,383 (6.9); 6.319 (1.0); 6.297 (1.5); 6.274 (1.1); 6.253 (0.3); 4,542 (1.2); 4,525 (3,4); 4,507 (3,4); 4,490 (1,1); 3,325 (179.5); 2,676 (1.0); 2,672 (1.5); 2,667 (1,1); 2,525 (7.4); 2,511 (88.9); 2,507 (176,0); 2,502 (231.2); 2,498 (170.2); 2,494 (85.7); 2.334 (1.2); 2,329 (1.6); 2.325 (1.2); 2.075 (0.8); 1,858 (2.1); 1,847 (4.6); 1,838 (5.0); 1,829 (2.1); 1.355 (1.7); 1,273 (2,6); 1,263
(5.2) ; 1,254 (5,4); 1,243 (3,1); 1,231 (6,2); 1,214 (10,9); 1,196 (5,5); 0,853 (0,3); 0,785 (0,5); 0,768 (0,6); 0,146 (0,3);(5.2); 1,254 (5.4); 1,243 (3,1); 1,231 (6.2); 1.214 (10.9); 1.196 (5.5); 0.853 (0.3); 0.785 (0.5); 0.768 (0.6); 0.146 (0.3);
0,008 (3,0); 0,000 (75,9); -0,008 (3,3); -0,149 (0,4) 0.008 (3.0); 0.000 (75.9); -0.008 (3.3); -0.149 (0.4)
Beispiel I-06: 1H-NMR (400,0 MHz, d6-DMSO): Example I-06: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,765 (4,1); 9,662 (4,3); 9,638 (4,4); 8,867 (9,4); 8,773 (4,1); 8,316 (1,3); 8,197 (3,6); 8,192 (3,7); 8,181 (3,7); 8,176 (3,5); 8,111 (14,1); 7,839 (2,0); 7,834 (2,1); 7,828 (2,3); 7,819 (2,7); 7,799 (12,9); 7,524 (3,8); 7,502 (7,0); 7,481 (3,3); 7,373 (11,2); 6,249 (0,5); 6,228 (1,8); 6,206 (2,7); 6,183 (1,9); 6,161 (0,6); 5,757 (2,4); 4,543 (2,1); 4,525 (5,6); 4,508 (5,5); 4,490 (2,0); 4,020 (0,4); 3,405 (0,4); 3,323 (425,4); 2,890 (0,5); 2,731 (0,5); 2,671 (4,3); 2,666 (3,3); 2,624 (0,5); 2,506 (470,3); 2,502 (586,2); 2,497 (445,2); 2,373 (0,3); 2,333 (3,2); 2,328 (4,0); 2,324 (3,1); 2,086 (5,9); 1,989 (1,3); 1,856 (3,5); 1,846 (7,8); 1,837 (8,2); 1,828 (3,5); 1,271 (3,8); 1,261 (8,3); 1,252 (8,3); 1,242 (3,8); 1,225 (8,0); 1,208 δ = 9.765 (4.1); 9,662 (4,3); 9,638 (4.4); 8,867 (9.4); 8,773 (4,1); 8.316 (1.3); 8,197 (3.6); 8,192 (3.7); 8,181 (3.7); 8.176 (3.5); 8,111 (14,1); 7,839 (2.0); 7,834 (2,1); 7.828 (2.3); 7,819 (2.7); 7,799 (12.9); 7,524 (3.8); 7,502 (7.0); 7,481 (3,3); 7,373 (11,2); 6.249 (0.5); 6.228 (1.8); 6,206 (2,7); 6.183 (1.9); 6.161 (0.6); 5,757 (2,4); 4,543 (2.1); 4,525 (5.6); 4,508 (5.5); 4,490 (2.0); 4,020 (0.4); 3.405 (0.4); 3,323 (425.4); 2,890 (0.5); 2,731 (0.5); 2,671 (4.3); 2,666 (3.3); 2,624 (0.5); 2,506 (470,3); 2,502 (586,2); 2,497 (445.2); 2.373 (0.3); 2.333 (3.2); 2,328 (4.0); 2,324 (3.1); 2.086 (5.9); 1,989 (1.3); 1,856 (3.5); 1,846 (7.8); 1,837 (8.2); 1,828 (3.5); 1,271 (3.8); 1,261 (8.3); 1,252 (8,3); 1,242 (3.8); 1,225 (8.0); 1,208
(16,0); 1,190 (7,6); 1,175 (1,1); 1,157 (0,6); 1,148 (0,7); 0,146 (0,9); 0,000 (178,6); -0,150 (0,9) (16.0); 1,190 (7.6); 1,175 (1.1); 1.157 (0.6); 1,148 (0.7); 0.146 (0.9); 0.000 (178.6); -0.150 (0.9)
Beispiel I-07: 1H-NMR (400,0 MHz, d6-DMSO): Example I-07: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,797 (4,3); 9,772 (6,8); 8,867 (9,3); 8,773 (3,4); 8,336 (5,8); 8,333 (5,8); 8,317 (0,4); 8,118 (16,0); 8,104 (2,9); 8,082 δ = 9.797 (4.3); 9,772 (6.8); 8,867 (9.3); 8,773 (3,4); 8,336 (5.8); 8,333 (5.8); 8.317 (0.4); 8.118 (16.0); 8,104 (2,9); 8,082
(3.3) ; 8,079 (3,2); 7,892 (6,0); 7,871 (5,0); 7,802 (11,1); 7,371 (11,0); 6,405 (0,4); 6,384 (1,6); 6,362 (2,4); 6,340 (1,7); 6,318 (0,5); 4,539 (1,7); 4,522 (4,9); 4,504 (4,8); 4,486 (1,6); 3,324 (238,7); 2,680 (0,7); 2,676 (1,5); 2,671 (2,1); 2,667 (1 ,5); 2,662 (0,7); 2,524 (7,3); 2,511 (118,7); 2,507 (232,8); 2,502 (302,9); 2,498 (218,1); 2,493 (104,6); 2,338 (0,7); 2,333 (1,5); 2,329 (2,0); 2,324 (1,5); 1,989 (0,7); 1,857 (3,2); 1,847 (6,9); 1,838 (7,5); 1,828 (3,1); 1,397 (14,5); 1,271 (3,3); 1,261 (7,4); 1,252 (7,4); 1,242 (3,1); 1,222 (7,4); 1,204 (15,7); 1,187 (7,1); 1,175 (0,8); 0,008 (1,5); 0,000 (40,3); -(3.3); 8.079 (3.2); 7,892 (6.0); 7,871 (5.0); 7,802 (11,1); 7,371 (11.0); 6,405 (0.4); 6.384 (1.6); 6,362 (2,4); 6.340 (1.7); 6.318 (0.5); 4,539 (1.7); 4,522 (4.9); 4,504 (4,8); 4,486 (1.6); 3,324 (238.7); 2,680 (0.7); 2,676 (1.5); 2,671 (2.1); 2,667 (1, 5); 2,662 (0.7); 2,524 (7.3); 2,511 (118.7); 2,507 (232,8); 2,502 (302.9); 2,498 (218.1); 2,493 (104.6); 2.338 (0.7); 2.333 (1.5); 2.329 (2.0); 2.324 (1.5); 1,989 (0.7); 1,857 (3.2); 1,847 (6.9); 1,838 (7.5); 1,828 (3,1); 1,397 (14.5); 1,271 (3.3); 1,261 (7.4); 1,252 (7.4); 1,242 (3,1); 1,222 (7.4); 1.204 (15.7); 1,187 (7.1); 1,175 (0.8); 0.008 (1.5); 0,000 (40.3); -
0,009 (1,4) 0.009 (1.4)
Beispiel I-08: 1H-NMR (601,6 MHz, d6-DMSO): Example I-08: 1 H NMR (601.6 MHz, d 6 -DMSO):
δ= 9,770 (1,5); 9,757 (1,1); 9,741 (1,0); 8,893 (3,8); 8,776 (1,4); 8,277 (0,9); 8,265 (1,5); 8,252 (0,8); 8,119 (5,9); 7,782 (4,3); 7,421 (4,1); 6,360 (0,5); 6,347 (0,8); 6,332 (0,6); 3,951 (16,0); 3,904 (3,1); 3,355 (1,1); 3,332 (1376,9); 3,296 (0,6); 3,285 (0,4); 3,172 (0,5); 3,163 (0,5); 3,029 (0,4); 2,617 (2,2); 2,614 (3,0); 2,611 (2,2); 2,541 (0,8); 2,523 (4,8); 2,520 (6,1); 2,517 (6,2); 2,508 (154,6); 2,505 (334,6); 2,502 (461,9); 2,499 (336,2); 2,496 (158,9); 2,389 (2,1); 2,386 (2,9); 2,383 (2,2); 1,902 (0,6); 1,851 (1,2); 1,845 (2,6); 1,839 (3,1); 1,834(1,3); 1,434 (0,6); 1,298 (0,6); 1,268(1,4); 1,262δ = 9.770 (1.5); 9.757 (1.1); 9.741 (1.0); 8,893 (3.8); 8.776 (1.4); 8.277 (0.9); 8.265 (1.5); 8.252 (0.8); 8.119 (5.9); 7,782 (4,3); 7,421 (4,1); 6,360 (0.5); 6,347 (0.8); 6.332 (0.6); 3,951 (16.0); 3.904 (3.1); 3.355 (1.1); 3,332 (1376.9); 3.296 (0.6); 3,285 (0.4); 3.172 (0.5); 3.163 (0.5); 3,029 (0.4); 2,617 (2,2); 2,614 (3.0); 2,611 (2,2); 2,541 (0.8); 2,523 (4,8); 2,520 (6.1); 2,517 (6.2); 2,508 (154.6); 2,505 (334.6); 2,502 (461.9); 2,499 (336.2); 2,496 (158.9); 2.389 (2.1); 2.386 (2.9); 2.383 (2.2); 1.902 (0.6); 1,851 (1.2); 1,845 (2.6); 1,839 (3.1); 1,834 (1.3); 1,434 (0.6); 1,298 (0.6); 1,268 (1.4); 1,262
(3.1) ; 1,255 (3,4); 1,249 (1,6); 1,244 (1,2); 1,235 (0,6); 0,005 (0,6); 0,000 (18,1); -0,006 (0,6) (3.1); 1.255 (3.4); 1,249 (1.6); 1,244 (1,2); 1.235 (0.6); 0.005 (0.6); 0.000 (18.1); -0.006 (0.6)
Beispiel I-09: 1H-NMR (400,0 MHz, d6-DMSO): Example I-09: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,770 (3,7); 9,661 (4,2); 9,636 (4,3); 8,871 (9,1); 8,774 (3,7); 8,119 (14,6); 8,038 (7,4); 7,958 (3,7); 7,934 (3,7); 7,852 (0,5); 7,807 (11,2); 7,715 (0,5); 7,404 (0,5); 7,386 (11,2); 6,339 (0,4); 6,318 (1,6); 6,296 (2,4); 6,274 (1,7); 6,252 (0,5); 4,545 (1,9); 4,528 (5,2); 4,510 (5,2); 4,493 (1,8); 4,056 (0,9); 4,038 (2,6); 4,020 (2,7); 4,003 (0,9); 3,324 (108,4); 3,031δ = 9.770 (3.7); 9,661 (4,2); 9,636 (4.3); 8,871 (9.1); 8,774 (3.7); 8.119 (14.6); 8.038 (7.4); 7,958 (3.7); 7,934 (3.7); 7.852 (0.5); 7,807 (11.2); 7.715 (0.5); 7.404 (0.5); 7,386 (11,2); 6,339 (0.4); 6.318 (1.6); 6.296 (2.4); 6.274 (1.7); 6.252 (0.5); 4,545 (1.9); 4,528 (5.2); 4,510 (5.2); 4.493 (1.8); 4.056 (0.9); 4.038 (2.6); 4,020 (2.7); 4,003 (0.9); 3,324 (108.4); 3,031
(1.0) ; 2,772 (0,9); 2,676 (1,3); 2,671 (1,7); 2,667 (1,2); 2,507 (194,3); 2,502 (247,6); 2,498 (181,1); 2,333 (1,2); 2,329 (1 ,6); 2,325 (1 ,2); 1 ,989 (11 ,3); 1 ,858 (3,2); 1 ,848 (7,2); 1 ,839 (7,7); 1 ,830 (3,2); 1 ,397 (8,7); 1 ,352 (0,5); 1 ,335 (0,5); 1,314 (0,4); 1,298 (0,5); 1,273 (3,6); 1,263 (8,0); 1,254 (8,2); 1,243 (4,6); 1,232 (9,7); 1,214 (16,0); 1,197 (7,7); 1,175(1.0); 2,772 (0.9); 2,676 (1.3); 2,671 (1.7); 2,667 (1.2); 2,507 (194,3); 2,502 (247.6); 2,498 (181,1); 2.333 (1.2); 2,329 (1,6); 2.325 (1, 2); 1, 989 (11, 3); 1, 858 (3,2); 1, 848 (7,2); 1, 839 (7, 7); 1, 830 (3,2); 1, 397 (8,7); 1, 352 (0.5); 1, 335 (0.5); 1,314 (0.4); 1,298 (0.5); 1,273 (3.6); 1,263 (8,0); 1,254 (8.2); 1,243 (4,6); 1,232 (9.7); 1,214 (16,0); 1,197 (7.7); 1,175
(6.2) ; 1,157 (3,2); 0,853 (0,4); 0,146 (0,7); 0,008 (6,6); 0,000 (149,7); -0,008 (6,4); -0,150 (0,7) (6.2); 1.157 (3.2); 0.853 (0.4); 0.146 (0.7); 0.008 (6.6); 0.000 (149.7); -0.008 (6.4); -0.150 (0.7)
Beispiel 1-10: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-10: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,768 (3,2); 9,753 (4,0); 9,729 (3,7); 8,870 (7,9); 8,772 (3,1); 8,316 (0,5); 8,125 (16,0); 8,067 (2,4); 8,044 (2,4); 7,832 (2,6); 7,805 (11,0); 7,388 (9,4); 6,439 (0,4); 6,418 (1,4); 6,397 (2,0); 6,375 (1,5); 6,352 (0,4); 4,544 (1,5); 4,527 (4,2); 4,509 (4,1); 4,492 (1,4); 3,324 (114,8); 2,676 (0,9); 2,672 (1,2); 2,667 (0,9); 2,542 (0,9); 2,511 (72,0); 2,507 (140,1); 2,503 (181,6); 2,498 (131,7); 2,494 (64,1); 2,334 (0,8); 2,329 (1,2); 2,325 (0,8); 2,075 (8,5); 1,858 (2,8); 1,848 (6,1); 1,839 (6,6); 1,830 (2,7); 1,272 (2,9); 1,262 (6,6); 1,253 (6,5); 1,243 (2,8); 1,227 (6,4); 1,209 (13,3); 1,192 (6,1); 0,008δ = 9.768 (3.2); 9,753 (4.0); 9,729 (3.7); 8,870 (7.9); 8,772 (3,1); 8.316 (0.5); 8.125 (16.0); 8.067 (2.4); 8.044 (2.4); 7.832 (2.6); 7,805 (11.0); 7,388 (9.4); 6,439 (0.4); 6.418 (1.4); 6.397 (2.0); 6.375 (1.5); 6,352 (0.4); 4,544 (1.5); 4,527 (4,2); 4,509 (4.1); 4,492 (1.4); 3,324 (114.8); 2,676 (0.9); 2,672 (1,2); 2,667 (0.9); 2,542 (0.9); 2,511 (72.0); 2,507 (140.1); 2,503 (181.6); 2,498 (131.7); 2,494 (64.1); 2.334 (0.8); 2,329 (1.2); 2.325 (0.8); 2.075 (8.5); 1,858 (2.8); 1,848 (6.1); 1,839 (6.6); 1,830 (2.7); 1,272 (2.9); 1,262 (6,6); 1,253 (6.5); 1,243 (2.8); 1,227 (6.4); 1,209 (13.3); 1,192 (6.1); 0,008
(3.2) ; 0,000 (73,7); -0,008 (2,8) (3.2); 0,000 (73.7); -0.008 (2.8)
Beispiel 1-11: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-11: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,851 (4,3); 9,827 (4,5); 9,765 (4,0); 8,869 (9,6); 8,777 (4,0); 8,106 (15,0); 7,914 (2,0); 7,896 (3,8); 7,878 (2,2); 7,806 (11,6); 7,753 (2,1); 7,750 (2,2); 7,732 (4,4); 7,714 (2,5); 7,711 (2,3); 7,431 (3,1); 7,411 (5,8); 7,399 (11,8); 6,400 (0,5); 6,380 (1 ,9); 6,358 (2,9); 6,336 (2,0); 6,314 (0,6); 4,544 (1 ,9); 4,527 (5,3); 4,509 (5,3); 4,491 (1 ,9); 3,326 (42,0); 2,892 (0,6); 2,732 (0,6); 2,690 (0,6); 2,672 (0,7); 2,507 (82,4); 2,503 (104,7); 2,499 (78,3); 2,330 (0,6); 1,858 (3,3); 1,847 (7,6); 1,838 (8,1); 1,829 (3,3); 1,397 (8,1); 1,273 (3,7); 1,263 (8,1); 1,254 (8,1); 1,244 (3,7); 1,223 (7,8); 1,205(16,0); 1,188δ = 9.851 (4.3); 9,827 (4,5); 9,765 (4.0); 8,869 (9.6); 8,777 (4.0); 8,106 (15.0); 7.914 (2.0); 7,896 (3.8); 7.878 (2.2); 7.806 (11.6); 7,753 (2,1); 7,750 (2.2); 7,732 (4.4); 7,714 (2.5); 7,711 (2,3); 7,431 (3,1); 7,411 (5.8); 7,399 (11.8); 6,400 (0.5); 6,380 (1, 9); 6,358 (2,9); 6.336 (2.0); 6.314 (0.6); 4,544 (1, 9); 4,527 (5.3); 4,509 (5.3); 4,491 (1, 9); 3,326 (42.0); 2,892 (0.6); 2,732 (0.6); 2,690 (0.6); 2,672 (0.7); 2,507 (82.4); 2,503 (104,7); 2,499 (78.3); 2,330 (0.6); 1,858 (3.3); 1,847 (7.6); 1,838 (8.1); 1,829 (3.3); 1,397 (8,1); 1,273 (3.7); 1,263 (8,1); 1,254 (8,1); 1,244 (3.7); 1,223 (7,8); 1.205 (16.0); 1,188
(7,4); 0,000 (16,5) (7.4); 0,000 (16.5)
Beispiel 1-12: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-12: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,841 (4,0); 9,817 (4,2); 9,774 (3,4); 8,901 (9,2); 8,783 (3,4); 8,315 (0,7); 8,267 (2,4); 8,249 (4,3); 8,230 (2,3); 8,157 (16,0); 7,904 (0,4); 7,848 (11 ,6); 7,495 (11,1); 6,388 (0,4); 6,368 (1 ,6); 6,347 (2,4); 6,325 (1 ,8); 6,303 (0,5); 5,479 (0,3); 5,437 (8,8); 3,321 (44,0); 3,226 (4,1); 3,220 (8,8); 3,214 (3,7); 2,676 (1,1); 2,671 (1,5); 2,667 (1,1); 2,662 (0,5); 2,541 (0,9); 2,524 (3,8); 2,511 (84,2); 2,506 (171,4); 2,502 (225,3); 2,497 (160,4); 2,493 (75,5); 2,338 (0,5); 2,333 (1,1); 2,329 (1,4); 2,324 (1,1); 2,320 (0,5); 2,074 (1,6); 1,861 (3,1); 1,852 (7,0); 1,842 (7,6); 1,833 (3,1); 1,754(1,4); 1,276 (3,5);δ = 9.841 (4.0); 9,817 (4,2); 9,774 (3,4); 8,901 (9,2); 8,783 (3,4); 8.315 (0.7); 8.267 (2.4); 8,249 (4.3); 8.230 (2.3); 8,157 (16,0); 7.904 (0.4); 7,848 (11, 6); 7,495 (11,1); 6,388 (0.4); 6,368 (1,6); 6,347 (2,4); 6.325 (1, 8); 6,303 (0.5); 5,479 (0.3); 5,437 (8,8); 3,321 (44.0); 3,226 (4,1); 3,220 (8,8); 3,214 (3.7); 2,676 (1.1); 2,671 (1.5); 2,667 (1,1); 2,662 (0.5); 2,541 (0.9); 2,524 (3.8); 2,511 (84,2); 2,506 (171.4); 2,502 (225.3); 2,497 (160.4); 2,493 (75.5); 2.338 (0.5); 2.333 (1.1); 2,329 (1.4); 2.324 (1.1); 2.320 (0.5); 2.074 (1.6); 1,861 (3.1); 1,852 (7.0); 1,842 (7.6); 1,833 (3,1); 1.754 (1.4); 1.276 (3.5);
1,267 (7,4); 1,257 (7,4); 1,247 (2,9); 0,146 (0,3); 0,008 (2,6); 0,000 (80,7); -0,009 (2,7); -0,150 (0,3) 1,267 (7.4); 1.257 (7.4); 1,247 (2.9); 0.146 (0.3); 0.008 (2.6); 0,000 (80.7); -0.009 (2.7); -0.150 (0.3)
Beispiel 1-13: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-13: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,685 (2,5); 9,661 (4,2); 8,872 (2,1); 8,659 (4,8); 8,340 (4,1); 8,104 (2,0); 8,083 (2,3); 7,961 (6,7); 7,887 (3,6); 7,866 (2,9); 7,500 (0,7); 7,466 (0,6); 7,431 (0,3); 7,410 (4,7); 7,331 (6,2); 7,319 (0,9); 6,872 (1,5); 6,642 (0,8); 6,375 (1,0); 6,353 (1,5); 6,330 (1,1); 5,757 (1,6); 4,520 (1,2); 4,503 (3,1); 4,486 (3,1); 4,468 (1,1); 3,602 (0,4); 3,325 (40,5); 3,027 (1,6); 2,759 (1,7); 2,676 (0,4); 2,672 (0,5); 2,668 (0,4); 2,507 (66,9); 2,503 (77,9); 2,499 (52,7); 2,455 (15,7); 2,330 (0,7); 2,320 (1,9); 2,185 (2,3); 1,854 (2,0); 1,844 (4,3); 1,835 (4,3); 1,826 (1,7); 1,760 (0,5); 1,357 (16,0); 1,249 (2,7); 1,239δ = 9.685 (2.5); 9,661 (4,2); 8,872 (2,1); 8,659 (4,8); 8,340 (4,1); 8.104 (2.0); 8,083 (2.3); 7,961 (6,7); 7,887 (3.6); 7,866 (2.9); 7,500 (0.7); 7.466 (0.6); 7,431 (0.3); 7,410 (4,7); 7,331 (6.2); 7,319 (0.9); 6,872 (1.5); 6.642 (0.8); 6.375 (1.0); 6,353 (1.5); 6.330 (1.1); 5,757 (1.6); 4,520 (1.2); 4,503 (3,1); 4,486 (3,1); 4.468 (1.1); 3,602 (0.4); 3,325 (40.5); 3.027 (1.6); 2,759 (1.7); 2,676 (0.4); 2,672 (0.5); 2,668 (0.4); 2,507 (66.9); 2,503 (77.9); 2,499 (52.7); 2,455 (15.7); 2,330 (0.7); 2,320 (1.9); 2.185 (2.3); 1,854 (2.0); 1,844 (4.3); 1,835 (4.3); 1,826 (1.7); 1,760 (0.5); 1,357 (16.0); 1,249 (2.7); 1,239
(6.8) ; 1,233 (8,1); 1,217 (9,4); 1,199 (4,2); 0,000 (10,5); -0,009 (0,3) (6.8); 1,233 (8,1); 1,217 (9.4); 1,199 (4.2); 0.000 (10.5); -0.009 (0.3)
Beispiel 1-14: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-14: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,770 (1,0); 9,685 (1,1); 9,662 (1,1); 8,897 (2,6); 8,783 (1,0); 8,315 (1,0); 8,152 (4,4); 8,109 (3,7); 8,093 (3,6); 7,892 (0,4); 7,853 (0,4); 7,841 (3,3); 7,499 (0,4); 7,480 (3,2); 6,305 (0,6); 6,282 (0,8); 6,263 (0,5); 5,445 (2,9); 5,441 (2,8); 3,790 (0,4); 3,332 (61,7); 3,217 (1,5); 3,211 (2,7); 3,205 (1,1); 2,675 (1,3); 2,671 (1,8); 2,666 (1,3); 2,541 (0,8); 2,524δ = 9.770 (1.0); 9.685 (1.1); 9.662 (1.1); 8.897 (2.6); 8,783 (1.0); 8.315 (1.0); 8,152 (4,4); 8,109 (3,7); 8,093 (3.6); 7,892 (0.4); 7,853 (0.4); 7,841 (3.3); 7,499 (0.4); 7,480 (3.2); 6,305 (0.6); 6.282 (0.8); 6.263 (0.5); 5,445 (2.9); 5,441 (2,8); 3,790 (0.4); 3,332 (61.7); 3,217 (1.5); 3,211 (2.7); 3.205 (1.1); 2.675 (1.3); 2,671 (1.8); 2,666 (1.3); 2,541 (0.8); 2,524
(4.3) ; 2,510 (107,0); 2,506 (216,0); 2,502 (283,0); 2,497 (202,9); 2,493 (97,3); 2,333 (1,4); 2,328 (1,9); 2,324 (1,3); 2,196 (0,5); 2,179 (1,1); 2,160 (0,6); 1,861 (0,9); 1,851 (2,0); 1,842 (2,3); 1,832 (1,0); 1,593 (0,4); 1,579 (0,3); 1,506(4.3); 2,510 (107.0); 2,506 (216,0); 2,502 (283,0); 2,497 (202.9); 2,493 (97.3); 2.333 (1.4); 2,328 (1.9); 2,324 (1.3); 2.196 (0.5); 2.179 (1.1); 2,160 (0.6); 1,861 (0.9); 1,851 (2.0); 1,842 (2.3); 1,832 (1.0); 1,593 (0.4); 1,579 (0.3); 1,506
(1.9) ; 1,477 (0,4); 1,469 (0,3); 1,276 (1,4); 1,266 (2,7); 1,257 (3,1); 1,235 (16,0); 0,871 (0,5); 0,854 (1,6); 0,837 (0,8);(1.9); 1,477 (0.4); 1.469 (0.3); 1.276 (1.4); 1,266 (2.7); 1,257 (3,1); 1,235 (16.0); 0.871 (0.5); 0.854 (1.6); 0.837 (0.8);
0,008 (0,3); 0,000 (12,0); -0,008 (0,4) 0.008 (0.3); 0,000 (12,0); -0.008 (0.4)
Beispiel 1-15: 1H-NMR (601,6 MHz, d6-DMSO): Example 1-15: 1 H NMR (601.6 MHz, d 6 -DMSO):
δ= 9,761 (1,3); 9,598 (1,6); 9,582 (1,7); 8,883 (3,6); 8,769 (1,3); 8,314 (0,5); 8,112 (9,9); 8,102 (4,2); 8,082 (0,4); 7,766δ = 9.761 (1.3); 9,598 (1.6); 9.582 (1.7); 8,883 (3.6); 8.769 (1.3); 8.314 (0.5); 8,112 (9.9); 8,102 (4,2); 8,082 (0.4); 7,766
(4.1) ; 7,749 (0,3); 7,397 (3,9); 6,286 (0,6); 6,271 (0,9); 6,256 (0,6); 3,972 (0,6); 3,969 (0,9); 3,951 (16,0); 3,866 (0,7); 3,849 (0,4); 3,846 (0,4); 3,840 (1,2); 3,808 (0,7); 3,805 (0,7); 3,796 (0,4); 3,790 (1,0); 3,776 (0,3); 3,339 (15,4); 2,731 (0,4); 2,617 (0,8); 2,614 (1,1); 2,611 (0,8); 2,608 (0,4); 2,541 (0,4); 2,523 (1,7); 2,520 (2,1); 2,517 (1,9); 2,508 (48,3); 2,505 (107,9); 2,502 (152,9); 2,499 (109,9); 2,496 (52,4); 2,392 (0,3); 2,389 (0,7); 2,386 (1,0); 2,383 (0,7); 2,380 (0,4); 1,989 (0,3); 1,853(1,2); 1,847 (2,8); 1,841 (3,2); 1,834(1,3); 1,398(1,0); 1,270 (1,3); 1,264 (2,9); 1,257(3,3); 1,251(4.1); 7,749 (0.3); 7,397 (3.9); 6.286 (0.6); 6.271 (0.9); 6.256 (0.6); 3,972 (0.6); 3,969 (0.9); 3,951 (16.0); 3.866 (0.7); 3.849 (0.4); 3,846 (0.4); 3.840 (1.2); 3,808 (0.7); 3.805 (0.7); 3,796 (0.4); 3,790 (1.0); 3,776 (0.3); 3,339 (15.4); 2,731 (0.4); 2,617 (0.8); 2,614 (1.1); 2,611 (0.8); 2.608 (0.4); 2,541 (0.4); 2,523 (1.7); 2,520 (2,1); 2,517 (1.9); 2,508 (48.3); 2,505 (107.9); 2,502 (152.9); 2,499 (109.9); 2,496 (52.4); 2,392 (0.3); 2.389 (0.7); 2.386 (1.0); 2.383 (0.7); 2,380 (0.4); 1,989 (0.3); 1,853 (1.2); 1,847 (2.8); 1,841 (3.2); 1,834 (1.3); 1,398 (1.0); 1,270 (1.3); 1,264 (2.9); 1.257 (3.3); 1,251
(1.4) ; 1,236 (1,4); 0,005 (1,0); 0,000 (42,1); -0,006 (1,7) (1.4); 1,236 (1.4); 0.005 (1.0); 0,000 (42.1); -0.006 (1.7)
Beispiel 1-16: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-16: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,762 (3,2); 9,737 (1,9); 8,883 (3,8); 8,777 (1,5); 8,338 (2,6); 8,316 (0,5); 8,113 (6,5); 8,084 (1,5); 7,887 (2,7); 7,866δ = 9.762 (3.2); 9,737 (1.9); 8,883 (3.8); 8.777 (1.5); 8.338 (2.6); 8.316 (0.5); 8,113 (6.5); 8,084 (1.5); 7,887 (2.7); 7,866
(2.2) ; 7,764 (4,9); 7,399 (4,8); 6,378 (0,7); 6,356 (1,1); 6,334 (0,8); 3,947 (16,0); 3,324 (154,0); 2,728 (0,4); 2,676 (1,0); 2,671 (1,4); 2,667 (1,0); 2,541 (1,0); 2,524 (4,4); 2,511 (81,8); 2,506 (161,0); 2,502 (208,9); 2,498 (150,5); 2,333 (1,0); 2,329 (1,3); 2,324 (1,0); 1,989 (1,1); 1,858(1,3); 1,847 (3,0); 1,838 (3,3); 1,829 (1,3); 1,398 (1,6); 1,273 (1,4); 1,263(2.2); 7,764 (4.9); 7,399 (4,8); 6.378 (0.7); 6.356 (1.1); 6.334 (0.8); 3,947 (16.0); 3,324 (154.0); 2,728 (0.4); 2,676 (1.0); 2,671 (1.4); 2,667 (1.0); 2,541 (1.0); 2,524 (4.4); 2,511 (81.8); 2,506 (161,0); 2,502 (208.9); 2,498 (150.5); 2.333 (1.0); 2,329 (1,3); 2,324 (1.0); 1,989 (1.1); 1,858 (1.3); 1,847 (3.0); 1,838 (3.3); 1,829 (1.3); 1,398 (1.6); 1,273 (1.4); 1,263
(3,2); 1,254 (3,2); 1,243 (1,4); 1,236 (0,8); 1,193 (0,3); 1,175 (0,6); 0,000 (1,1) (3.2); 1.254 (3.2); 1,243 (1.4); 1,236 (0.8); 1.193 (0.3); 1,175 (0.6); 0,000 (1.1)
Beispiel 1-17: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-17: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,779 (6,3); 9,755 (3,7); 8,879 (7,9); 8,774 (3,1); 8,317 (0,4); 8,282 (2,1); 8,264 (3,7); 8,245 (2,0); 8,127 (13,3); 7,817 (9,9); 7,407 (10,0); 6,396 (0,4); 6,377 (1,4); 6,356 (2,1); 6,333 (1,5); 6,312 (0,5); 4,544 (1,5); 4,527 (4,4); 4,509 (4,4); 4,492 (1,5); 3,333 (219,9); 2,677 (0,6); 2,672 (0,8); 2,668 (0,6); 2,542 (0,4); 2,525 (2,3); 2,512 (49,8); 2,508 (100,5); 2,503 (132,2); 2,499 (95,0); 2,495 (45,5); 2,335 (0,6); 2,330 (0,8); 2,325 (0,6); 2,076 (16,0); 1,858 (2,8); 1,849 (6,2); 1,839 (6,8); 1,830 (2,8); 1,273 (3,1); 1,263 (6,7); 1,254(6,8); 1,244 (3,2); 1,234 (7,0); 1,217(14,0); 1,199 (6,4); 0,008δ = 9.779 (6.3); 9,755 (3.7); 8,879 (7.9); 8,774 (3.1); 8.317 (0.4); 8,282 (2,1); 8,264 (3.7); 8.245 (2.0); 8,127 (13.3); 7,817 (9.9); 7,407 (10.0); 6.396 (0.4); 6,377 (1.4); 6,356 (2,1); 6,333 (1.5); 6.312 (0.5); 4,544 (1.5); 4,527 (4.4); 4,509 (4.4); 4,492 (1.5); 3,333 (219.9); 2,677 (0.6); 2,672 (0.8); 2,668 (0.6); 2,542 (0.4); 2.525 (2.3); 2,512 (49,8); 2,508 (100.5); 2,503 (132,2); 2,499 (95.0); 2,495 (45.5); 2.335 (0.6); 2,330 (0.8); 2.325 (0.6); 2.076 (16.0); 1,858 (2.8); 1,849 (6.2); 1,839 (6.8); 1,830 (2.8); 1,273 (3,1); 1,263 (6,7); 1,254 (6.8); 1,244 (3.2); 1,234 (7.0); 1,217 (14.0); 1,199 (6.4); 0,008
(1,2); 0,000 (32,7); -0,009 (1,2) (1,2); 0,000 (32,7); -0.009 (1.2)
Beispiel 1-18: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-18: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,774 (7,1); 9,751 (4,4); 8,875 (9,2); 8,767 (3,5); 8,316 (0,5); 8,281 (2,4); 8,263 (4,3); 8,244 (2,3); 8,124 (15,5); 7,815 (11 ,3); 7,406 (11 ,3); 6,396 (0,5); 6,376 (1 ,6); 6,355 (2,4); 6,333 (1 ,8); 6,311 (0,5); 4,544 (1 ,8); 4,527 (5,1); 4,509 (5,0); 4,491 (1,7); 3,325 (206,2); 2,676 (1,0); 2,671 (1,4); 2,667 (1,0); 2,542 (0,8); 2,525 (3,9); 2,511 (77,8); 2,507 (157,1);δ = 9.774 (7.1); 9,751 (4.4); 8,875 (9,2); 8,767 (3.5); 8.316 (0.5); 8,281 (2,4); 8,263 (4,3); 8.244 (2.3); 8,124 (15.5); 7,815 (11, 3); 7,406 (11, 3); 6.396 (0.5); 6,376 (1,6); 6,355 (2,4); 6,333 (1, 8); 6.311 (0.5); 4,544 (1, 8); 4,527 (5.1); 4,509 (5.0); 4.491 (1.7); 3,325 (206,2); 2,676 (1.0); 2,671 (1.4); 2,667 (1.0); 2,542 (0.8); 2,525 (3.9); 2,511 (77.8); 2,507 (157,1);
2.502 (206,8); 2,498 (148,5); 2,494 (71,1); 2,334 (0,9); 2,329 (1,3); 2,325 (0,9); 2,075 (0,5); 1,858 (3,2); 1,848 (7,1); 1,839 (7,7); 1,829 (3,1); 1,273 (3,5); 1,263 (7,6); 1,254 (7,7); 1,243 (3,6); 1,234 (7,8); 1,216(16,0); 1,199 (7,3); 0,1462,502 (206.8); 2,498 (148.5); 2,494 (71.1); 2,334 (0.9); 2,329 (1,3); 2.325 (0.9); 2.075 (0.5); 1,858 (3.2); 1,848 (7.1); 1,839 (7.7); 1,829 (3,1); 1,273 (3.5); 1,263 (7.6); 1,254 (7.7); 1,243 (3.6); 1,234 (7.8); 1,216 (16.0); 1,199 (7.3); 0.146
(1.2) ; 0,008 (10,1); 0,000 (270,9); -0,009 (10,2); -0,150 (1,2) (1.2); 0.008 (10.1); 0.000 (270.9); -0.009 (10.2); -0.150 (1.2)
Beispiel 1-19: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-19: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,844 (4,6); 9,820 (4,8); 9,774 (4,2); 8,898 (10,1); 8,791 (4,1); 8,332 (7,0); 8,317 (0,6); 8,154 (16,0); 8,103 (3,3); 8,082 (3,9); 7,893 (6,9); 7,872 (5,7); 7,840 (12,7); 7,477 (12,4); 6,414 (0,5); 6,393 (1,8); 6,371 (2,8); 6,348 (2,0); 6,326 (0,5); 5,492 (0,4); 5,486 (0,5); 5,442 (10,6); 5,399 (0,4); 5,393 (0,4); 4,056 (0,5); 4,038 (1,5); 4,020 (1,5); 4,003 (0,5); 3,325 (122,4); 3,212 (4,3); 3,206 (8,6); 3,200 (4,1); 2,676 (0,9); 2,671 (1,3); 2,507 (148,3); 2,502 (190,1); 2,498 (139,2); 2,329 (1,2); 1,989 (6,4); 1,862 (3,5); 1,851 (7,8); 1,843 (8,4); 1,833 (3,5); 1,397 (10,9); 1,275 (3,7); 1,265 (8,3); 1,257δ = 9.844 (4.6); 9,820 (4,8); 9,774 (4.2); 8,898 (10.1); 8,791 (4,1); 8,332 (7.0); 8.317 (0.6); 8,154 (16.0); 8,103 (3,3); 8,082 (3.9); 7,893 (6.9); 7,872 (5.7); 7,840 (12,7); 7,477 (12.4); 6,414 (0.5); 6,393 (1.8); 6,371 (2,8); 6.348 (2.0); 6,326 (0.5); 5,492 (0.4); 5.486 (0.5); 5.442 (10.6); 5,399 (0.4); 5,393 (0.4); 4.056 (0.5); 4,038 (1.5); 4,020 (1.5); 4.003 (0.5); 3,325 (122.4); 3,212 (4,3); 3,206 (8,6); 3,200 (4.1); 2,676 (0.9); 2,671 (1.3); 2,507 (148.3); 2,502 (190.1); 2,498 (139.2); 2,329 (1.2); 1,989 (6.4); 1,862 (3.5); 1,851 (7.8); 1,843 (8.4); 1,833 (3.5); 1.397 (10.9); 1,275 (3.7); 1,265 (8.3); 1.257
(8.3) ; 1,246 (3,4); 1,236 (1,4); 1,193 (1,7); 1,175 (3,3); 1,157 (1,7); 0,146 (1,1); 0,007 (11,9); 0,000 (218,0); -0,008(8.3); 1,246 (3,4); 1,236 (1.4); 1.193 (1.7); 1,175 (3.3); 1.157 (1.7); 0.146 (1.1); 0.007 (11.9); 0,000 (218,0); -0,008
(10,3); -0,150 (1,1) (10.3); -0.150 (1.1)
Beispiel I-20: 1H-NMR (400,0 MHz, d6-DMSO): Example I-20: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,767 (1,6); 9,634 (1,8); 9,609 (1,9); 8,889 (4,1); 8,777 (1,6); 8,154 (10,5); 8,117 (6,5); 7,769 (5,0); 7,401 (4,8); 6,313 (0,7); 6,292 (1,0); 6,270 (0,8); 3,951 (16,0); 3,328 (80,9); 3,309 (0,4); 2,672 (0,4); 2,525 (1,0); 2,507 (49,0); 2,503 (63,9); 2,499 (47,2); 2,330 (0,4); 1,860 (1,4); 1,849 (3,1); 1,840 (3,4); 1,831 (1,4); 1,275 (1,5); 1,266 (3,3); 1,256 (3,3); 1,246δ = 9.767 (1.6); 9,634 (1.8); 9,609 (1.9); 8,889 (4,1); 8,777 (1.6); 8.154 (10.5); 8,117 (6.5); 7,769 (5.0); 7,401 (4,8); 6.313 (0.7); 6.292 (1.0); 6.270 (0.8); 3,951 (16.0); 3,328 (80.9); 3.309 (0.4); 2,672 (0.4); 2,525 (1.0); 2,507 (49.0); 2,503 (63.9); 2,499 (47.2); 2,330 (0.4); 1,860 (1.4); 1,849 (3.1); 1,840 (3,4); 1,831 (1.4); 1.275 (1.5); 1,266 (3.3); 1.256 (3.3); 1,246
(1.3) ; 0,008 (1 ,2); 0,000 (31 ,6); -0,008 (1 ,3) (1.3); 0.008 (1, 2); 0,000 (31, 6); -0.008 (1, 3)
Beispiel 1-21: 1H-NMR (400,0 MHz, d6-DMSO): Example 1-21: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,775 (2,2); 9,715 (2,6); 9,691 (2,6); 8,901 (5,8); 8,789 (2,2); 8,316 (0,4); 8,156 (10,7); 8,147 (16,0); 7,844 (7,4); 7,483 (7,0); 6,326 (1,0); 6,304 (1,4); 6,282 (1,1); 5,445 (5,4); 5,442 (5,4); 3,326 (125,1); 3,221 (2,5); 3,215 (5,5); 3,209δ = 9.775 (2.2); 9.715 (2.6); 9,691 (2.6); 8,901 (5.8); 8.789 (2.2); 8.316 (0.4); 8,156 (10,7); 8.147 (16.0); 7,844 (7.4); 7,483 (7.0); 6,326 (1.0); 6,304 (1.4); 6.282 (1.1); 5,445 (5.4); 5,442 (5.4); 3,326 (125.1); 3,221 (2.5); 3,215 (5.5); 3,209
(2.4) ; 2,676 (0,6); 2,672 (0,8); 2,667 (0,6); 2,525 (2,3); 2,512 (44,4); 2,507 (90,3); 2,503 (120,0); 2,498 (87,0); 2,493 (42,0); 2,334 (0,6); 2,329 (0,8); 2,325 (0,6); 1,909 (0,6); 1,862 (2,0); 1,852 (4,4); 1,843 (4,8); 1,833 (2,0); 1,277 (2,1);(2.4); 2,676 (0.6); 2,672 (0.8); 2,667 (0.6); 2.525 (2.3); 2,512 (44.4); 2,507 (90.3); 2,503 (120,0); 2,498 (87.0); 2,493 (42.0); 2.334 (0.6); 2.329 (0.8); 2.325 (0.6); 1,909 (0.6); 1,862 (2.0); 1,852 (4.4); 1,843 (4,8); 1,833 (2.0); 1,277 (2,1);
1,267 (4,6); 1,258 (4,7); 1,247 (1,9); 1,235 (0,5); 0,008 (2,5); 0,000 (71,1); -0,009 (2,5) 1,267 (4,6); 1,258 (4,7); 1,247 (1.9); 1.235 (0.5); 0.008 (2.5); 0,000 (71.1); -0.009 (2.5)
Beispiel I-22: 1H-NMR (400,0 MHz, d6-DMSO): Example I-22: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,799 (0,6); 9,769 (4,5); 9,751 (4,8); 9,727 (4,4); 9,289 (0,6); 8,870 (9,0); 8,769 (4,3); 8,316 (0,9); 8,267 (7,9); 8,231 (7,9); 8,128 (12,7); 8,110 (0,6); 7,992 (7,6); 7,859 (0,9); 7,848 (1,1); 7,803 (10,6); 7,720 (0,5); 7,387 (11,1); 7,318 (0,5); 6,444 (0,5); 6,423 (1,8); 6,402 (2,7); 6,380 (1,9); 6,358 (0,6); 4,540 (2,1); 4,524 (5,8); 4,506 (5,9); 4,489 (2,2); 4,353 (0,4); 4,335 (0,4); 3,979 (0,5); 3,421 (0,4); 3,323 (201,1); 3,031 (1,2); 2,773 (1,1); 2,672 (2,3); 2,565 (0,6); 2,506 (268,9);δ = 9.799 (0.6); 9,769 (4,5); 9,751 (4,8); 9,727 (4.4); 9,289 (0.6); 8,870 (9.0); 8,769 (4,3); 8,316 (0.9); 8,267 (7.9); 8,231 (7.9); 8,128 (12,7); 8.110 (0.6); 7,992 (7.6); 7,859 (0.9); 7.848 (1.1); 7,803 (10,6); 7,720 (0.5); 7,387 (11,1); 7.318 (0.5); 6,444 (0.5); 6,423 (1.8); 6,402 (2,7); 6,380 (1.9); 6,358 (0.6); 4,540 (2.1); 4,524 (5.8); 4,506 (5.9); 4.489 (2.2); 4.353 (0.4); 4,335 (0.4); 3.979 (0.5); 3,421 (0.4); 3,323 (201,1); 3.031 (1.2); 2,773 (1.1); 2,672 (2,3); 2,565 (0.6); 2,506 (268,9);
2.503 (335,5); 2,329 (2,2); 1,858 (3,2); 1,848 (7,5); 1,839 (8,3); 1,831 (3,9); 1,585 (0,5); 1,580 (0,6); 1,364 (0,5); 1,347 (0,9); 1,329 (0,5); 1,315 (0,4); 1,298 (0,5); 1,272 (4,4); 1,262 (8,9); 1,253 (9,2); 1,236 (6,4); 1,226 (8,7); 1,208 (16,0);2,503 (335.5); 2,329 (2,2); 1,858 (3.2); 1,848 (7.5); 1,839 (8.3); 1,831 (3.9); 1.585 (0.5); 1,580 (0.6); 1,364 (0.5); 1,347 (0.9); 1.329 (0.5); 1.315 (0.4); 1,298 (0.5); 1,272 (4.4); 1,262 (8.9); 1,253 (9,2); 1,236 (6.4); 1,226 (8,7); 1,208 (16,0);
1,191 (7,7); 0,921 (0,5); 0,904 (0,5); 0,854 (0,5); 0,146 (1,3); 0,000 (264,2); -0,059 (0,3); -0,150 (1,3) 1,191 (7.7); 0.921 (0.5); 0.904 (0.5); 0.854 (0.5); 0.146 (1.3); 0,000 (264,2); -0.059 (0.3); -0.150 (1.3)
Beispiel I-23: 1H-NMR (400,0 MHz, d6-DMSO): Example I-23: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,767 (0,9); 9,397 (1,0); 9,374 (1,1); 8,868 (2,4); 8,782 (0,9); 8,103 (4,2); 7,785 (2,9); 7,389 (1,5); 7,373 (1,4); 7,368 (1,3); 7,354 (3,1); 7,301 (0,5); 7,284 (0,6); 7,278 (1,0); 7,273 (0,5); 7,261 (0,3); 7,255 (0,5); 6,403 (0,5); 6,392 (0,5); 4,550 (0,4); 4,532 (1,1); 4,513 (1,1); 4,495 (0,4); 3,326 (30,5); 2,525 (0,6); 2,511 (14,5); 2,507 (30,1); 2,502 (40,7); 2,498 (30,4); 2,493 (15,2); 1,989 (0,5); 1,858 (0,8); 1,847 (1,8); 1,838 (2,0); 1,829 (0,8); 1,398 (16,0); 1,273 (0,8); 1,263 (1,9); 1,254 (1,9); 1,243 (0,9); 1,225 (1,9); 1,208 (4,0); 1,190 (1,9); 1,175 (0,4); 0,008 (2,2); 0,000 (61,1); -0,009 (2,6) Beispiel I-24: 1H-NMR (400,0 MHz, d6-DMSO): δ = 9.767 (0.9); 9.397 (1.0); 9.374 (1.1); 8,868 (2,4); 8,782 (0.9); 8,103 (4,2); 7,785 (2.9); 7,389 (1.5); 7,373 (1.4); 7,368 (1,3); 7,354 (3,1); 7,301 (0.5); 7.284 (0.6); 7,278 (1.0); 7,273 (0.5); 7.261 (0.3); 7.255 (0.5); 6,403 (0.5); 6,392 (0.5); 4,550 (0.4); 4.532 (1.1); 4.513 (1.1); 4,495 (0.4); 3,326 (30.5); 2,525 (0.6); 2,511 (14.5); 2,507 (30.1); 2,502 (40,7); 2,498 (30.4); 2,493 (15,2); 1,989 (0.5); 1,858 (0.8); 1,847 (1.8); 1,838 (2.0); 1,829 (0.8); 1,398 (16.0); 1,273 (0.8); 1,263 (1.9); 1,254 (1.9); 1,243 (0.9); 1.225 (1.9); 1,208 (4.0); 1,190 (1.9); 1.175 (0.4); 0.008 (2.2); 0,000 (61.1); -0.009 (2.6) Example I-24: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,766 (3,5); 9,406 (3,7); 9,383 (3,8); 8,869 (8,2); 8,779 (3,4); 8,316 (0,6); 8,110 (12,7); 7,831 (0,8); 7,785 (10,0); 7,711 (13,6); 7,707 (16,0); 7,655 (4,3); 7,651 (6,9); 7,646 (3,9); 7,353 (10,4); 6,553 (1,0); 6,544 (0,9); 6,416 (1,9); 6,406 (1,9); 6,279 (1,0); 6,268 (1,1); 5,703 (0,4); 5,693 (0,6); 5,671 (1,2); 5,665 (1,2); 5,650 (1,0); 5,636 (1,2); 5,612 (0,6); 5,603 (0,5); 4,545 (1,7); 4,528 (4,7); 4,510 (4,6); 4,492 (1,7); 3,326 (144,3); 3,030 (2,0); 2,774 (1,9); 2,671 (1,3); 2,667 (1,0); 2,506 (146,9); 2,502 (193,1); 2,498 (149,3); 2,333 (1,0); 2,329 (1,3); 2,325 (1,0); 1,857 (2,9); 1,847 (6,5); 1,838 (7,0); 1,828 (3,0); 1,397 (14,6); 1,272 (3,2); 1,262 (7,0); 1,253 (7,2); 1,242 (3,5); 1,223 (7,0); 1,205 (14,0); 1,188 (6,5);δ = 9.766 (3.5); 9,406 (3.7); 9,383 (3.8); 8,869 (8.2); 8,779 (3,4); 8.316 (0.6); 8,110 (12,7); 7,831 (0.8); 7,785 (10.0); 7,711 (13.6); 7,707 (16.0); 7,655 (4.3); 7.651 (6.9); 7.646 (3.9); 7,353 (10.4); 6,553 (1.0); 6.544 (0.9); 6,416 (1.9); 6,406 (1.9); 6.279 (1.0); 6.268 (1.1); 5,703 (0.4); 5,693 (0.6); 5,671 (1,2); 5,665 (1.2); 5,650 (1.0); 5.636 (1.2); 5.612 (0.6); 5.603 (0.5); 4,545 (1.7); 4,528 (4,7); 4,510 (4,6); 4.492 (1.7); 3,326 (144.3); 3,030 (2.0); 2,774 (1.9); 2,671 (1.3); 2,667 (1.0); 2,506 (146.9); 2,502 (193.1); 2,498 (149.3); 2.333 (1.0); 2,329 (1,3); 2.325 (1.0); 1,857 (2.9); 1,847 (6.5); 1,838 (7.0); 1.828 (3.0); 1.397 (14.6); 1,272 (3,2); 1,262 (7.0); 1,253 (7.2); 1,242 (3.5); 1,223 (7.0); 1.205 (14.0); 1,188 (6.5);
0,146 (1,2); 0,008 (11,8); 0,000 (239,1); -0,008 (16,1); -0,150 (1,2) 0.146 (1.2); 0.008 (11.8); 0,000 (239,1); -0.008 (16.1); -0.150 (1.2)
Beispiel I-25: 1H-NMR (400,0 MHz, d6-DMSO): Example I-25: 1 H NMR (400.0 MHz, d 6 -DMSO):
δ= 9,763 (3,4); 9,419 (3,6); 9,396 (3,7); 8,864 (8,1); 8,777 (3,4); 8,316 (0,4); 8,101 (11,8); 8,036 (0,6); 7,952 (0,9); 7,907 (6,9); 7,903 (7,3); 7,812 (0,6); 7,781 (9,9); 7,727 (5,7); 7,707 (7,8); 7,596 (4,0); 7,592 (4,2); 7,575 (3,1); 7,571 (3,2); δ = 9.763 (3.4); 9,419 (3.6); 9.396 (3.7); 8,864 (8,1); 8.777 (3.4); 8.316 (0.4); 8,101 (11,8); 8.036 (0.6); 7.952 (0.9); 7,907 (6.9); 7,903 (7.3); 7.812 (0.6); 7,781 (9.9); 7,727 (5.7); 7,707 (7.8); 7,596 (4.0); 7,592 (4,2); 7,575 (3.1); 7,571 (3.2);
7,340 (10,2); 6,540 (1,0); 6,530 (0,9); 6,403 (1,9); 6,393 (2,0); 6,265 (1,0); 6,254 (1,1); 5,756 (1,8); 5,667 (0,5); 5,657 (0,6); 5,633 (1,3); 5,625 (1,2); 5,612 (1,1); 5,600 (1,4); 5,577 (0,6); 5,566 (0,5); 4,543 (1,7); 4,526 (4,8); 4,508 (4,8);  7,340 (10,2); 6.540 (1.0); 6.530 (0.9); 6,403 (1.9); 6,393 (2.0); 6.265 (1.0); 6.254 (1.1); 5,756 (1.8); 5,667 (0.5); 5.657 (0.6); 5.633 (1.3); 5.625 (1.2); 5.612 (1.1); 5,600 (1.4); 5,577 (0.6); 5.566 (0.5); 4,543 (1.7); 4,526 (4,8); 4,508 (4,8);
4.491 (1,8); 4,056 (1,2); 4,038 (3,8); 4,020 (3,9); 4,002 (1,3); 3,325 (169,3); 2,980 (0,3); 2,891 (5,4); 2,732 (4,8); 2,690 (2,1); 2,671 (1,1); 2,506 (124,7); 2,502 (164,1); 2,498 (130,1); 2,329 (1,1); 1,989 (16,0); 1,857 (2,7); 1,847 (6,2); 1,838 4,491 (1.8); 4.056 (1.2); 4,038 (3.8); 4,020 (3.9); 4.002 (1.3); 3,325 (169.3); 2,980 (0.3); 2,891 (5.4); 2,732 (4,8); 2,690 (2.1); 2,671 (1,1); 2,506 (124,7); 2,502 (164.1); 2,498 (130.1); 2,329 (1,1); 1,989 (16.0); 1,857 (2.7); 1,847 (6.2); 1,838
(6.8) ; 1,828 (3,0); 1,335 (0,4); 1,327 (0,5); 1,272 (3,0); 1,262 (6,6); 1,253 (6,8); 1,243 (3,0); 1,220 (6,8); 1,203 (13,9); (6.8); 1.828 (3.0); 1,335 (0.4); 1,327 (0.5); 1,272 (3.0); 1,262 (6,6); 1,253 (6.8); 1,243 (3.0); 1,220 (6.8); 1,203 (13,9);
1,193 (6,9); 1,185 (6,9); 1,175 (9,1); 1,157 (4,3); 1,006 (0,4); 0,999 (0,4); 0,146 (0,7); 0,000 (137,1); -0,150 (0,7)  1,193 (6.9); 1.185 (6.9); 1,175 (9.1); 1,157 (4,3); 1,006 (0.4); 0.999 (0.4); 0.146 (0.7); 0,000 (137.1); -0.150 (0.7)
Beispiel I-26: 1H-NMR (400,0 MHz, de-DMSO): Example I-26: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 9,813 (0,3); 9,784 (5,1); 9,775 (3,9); 9,760 (4,7); 9,298 (0,4); 8,877 (8,7); 8,769 (3,4); 8,317 (0,3); 8,126 (16,0); 8,108 (2,8); 8,094 (1,4); 7,865 (0,9); 7,861 (0,7); 7,817 (10,9); 7,409 (11,0); 6,393 (0,4); 6,373 (1,6); 6,351 (2,4); 6,329 (1,7); 6,308 (0,5); 4,546 (1,7);  δ = 9.813 (0.3); 9,784 (5.1); 9,775 (3.9); 9,760 (4,7); 9,298 (0.4); 8,877 (8.7); 8.769 (3.4); 8.317 (0.3); 8,126 (16.0); 8,108 (2,8); 8.094 (1.4); 7.865 (0.9); 7.861 (0.7); 7,817 (10.9); 7,409 (11.0); 6,393 (0.4); 6,373 (1.6); 6.351 (2.4); 6.329 (1.7); 6.308 (0.5); 4.546 (1.7);
4,528 (5,1); 4,511 (5,1); 4,493 (1,7); 3,327 (124,1); 2,676 (0,8); 2,672 (1,2); 2,667 (0,9); 2,525 (2,8); 2,511 (65,9); 2,507 (135,0);  4,528 (5.1); 4,511 (5.1); 4.493 (1.7); 3,327 (124,1); 2,676 (0.8); 2,672 (1,2); 2,667 (0.9); 2,525 (2.8); 2,511 (65.9); 2,507 (135.0);
2,503 (180,5); 2,498 (135,1); 2,494 (68,5); 2,334 (0,9); 2,329 (1,2); 2,325 (0,9); 2,075 (8,3); 1,858 (3,0); 1,848 (6,8); 1,839 (7,5);  2,503 (180.5); 2,498 (135.1); 2,494 (68.5); 2,334 (0.9); 2,329 (1.2); 2.325 (0.9); 2.075 (8.3); 1,858 (3.0); 1,848 (6.8); 1,839 (7.5);
1,830 (3,1); 1,589 (0,3); 1,582 (0,4); 1,286 (0,4); 1,273 (3,6); 1,263 (7,4); 1,254(7,5); 1,243 (3,5); 1,234(7,4); 1,216(15,5); 1,199  1,830 (3.1); 1,589 (0.3); 1,582 (0.4); 1,286 (0.4); 1,273 (3.6); 1,263 (7.4); 1,254 (7.5); 1,243 (3.5); 1,234 (7.4); 1,216 (15.5); 1,199
(7,1); 0,000 (2,5)  (7.1); 0,000 (2.5)
Beispiel I-27: 1H-NMR (400,0 MHz, de-DMSO): Example I-27: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 9,784 (4,9); 9,773 (3,9); 9,761 (5,0); 8,876 (9,2); 8,776 (3,4); 8,317 (0,4); 8,122 (15,7); 8,113 (2,7); 8,098 (2,6); 8,089 (2,6); 8,074 (2,4); 7,816 (11,4); 7,406 (11,4); 6,416 (0,4); 6,395 (1,6); 6,374 (2,3); 6,352 (1,7); 6,331 (0,5); 4,546 (1,6); 4,528 (4,5); 4,510 (4,4);  δ = 9.784 (4.9); 9,773 (3.9); 9,761 (5.0); 8,876 (9,2); 8.776 (3.4); 8.317 (0.4); 8,122 (15,7); 8,113 (2,7); 8,098 (2.6); 8,089 (2.6); 8.074 (2.4); 7,816 (11,4); 7,406 (11,4); 6.416 (0.4); 6,395 (1.6); 6.374 (2.3); 6,352 (1.7); 6.331 (0.5); 4,546 (1.6); 4,528 (4,5); 4,510 (4.4);
4.492 (1,6); 3,327 (71,9); 2,677 (0,6); 2,672 (0,9); 2,668 (0,7); 2,526 (2,1); 2,521 (3,1); 2,512 (46,7); 2,508 (97,2); 2,503 (130,7);  4,492 (1.6); 3,327 (71.9); 2,677 (0.6); 2,672 (0.9); 2,668 (0.7); 2,526 (2,1); 2,521 (3,1); 2,512 (46,7); 2,508 (97.2); 2,503 (130,7);
2,499 (96,2); 2,494 (47,1); 2,335 (0,6); 2,330 (0,9); 2,326 (0,6); 2,076 (6,3); 1,859 (3,1); 1,849 (7,1); 1,840 (7,7); 1,830 (3,2); 1,274 (3,4); 1,264 (7,6); 1,255 (7,7); 1,244 (3,5); 1,234 (7,7); 1,217 (16,0); 1,199 (7,3); 0,146 (1,0); 0,008 (7,3); 0,000 (219,6); -0,009 (8,2); - 2,499 (96.2); 2,494 (47.1); 2.335 (0.6); 2,330 (0.9); 2,326 (0.6); 2.076 (6.3); 1,859 (3.1); 1,849 (7.1); 1,840 (7.7); 1,830 (3.2); 1,274 (3,4); 1,264 (7.6); 1.255 (7.7); 1,244 (3.5); 1,234 (7,7); 1,217 (16,0); 1,199 (7.3); 0.146 (1.0); 0.008 (7.3); 0.000 (219.6); -0.009 (8.2); -
0,150 (1,0) 0.150 (1.0)
Beispiel I-28: 1H-NMR (400,0 MHz, de-DMSO): Example I-28: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 9,771 (3,5); 9,513 (0,4); 9,491 (0,5); 9,466 (3,9); 9,444 (4,0); 9,293 (0,8); 8,871 (9,2); 8,776 (3,5); 8,317 (0,6); 8,109 (15,2); 8,064 δ = 9.771 (3.5); 9.513 (0.4); 9.491 (0.5); 9,466 (3.9); 9.444 (4.0); 9.293 (0.8); 8,871 (9,2); 8.776 (3.5); 8.317 (0.6); 8,109 (15,2); 8,064
(3.0) ; 8,045 (5,0); 8,027 (2,9); 7,847 (1,4); 7,836 (1,0); 7,792 (11,2); 7,351 (11,9); 6,626 (1,0); 6,616 (1,0); 6,488 (2,1); 6,478 (2,2); (3.0); 8.045 (5.0); 8.027 (2.9); 7.847 (1.4); 7.836 (1.0); 7,792 (11.2); 7,351 (11.9); 6.626 (1.0); 6.616 (1.0); 6,488 (2,1); 6.478 (2.2);
6,351 (1,1); 6,340 (1,2); 5,885 (0,5); 5,875 (0,6); 5,853 (1,4); 5,843 (1,2); 5,833 (1,1); 5,820 (1,5); 5,798 (0,6); 5,787 (0,5); 4,559 (0,3); 4,541 (1,8); 4,523 (4,6); 4,504 (4,5); 4,486 (1,7); 4,468 (0,3); 3,329 (169,8); 2,676 (0,9); 2,672 (1,2); 2,667 (0,9); 2,525 (3,4);  6.351 (1.1); 6.340 (1.2); 5.885 (0.5); 5.875 (0.6); 5,853 (1.4); 5,843 (1.2); 5.833 (1.1); 5,820 (1.5); 5,798 (0.6); 5,787 (0.5); 4,559 (0.3); 4,541 (1.8); 4,523 (4,6); 4,504 (4,5); 4,486 (1.7); 4,468 (0.3); 3,329 (169.8); 2,676 (0.9); 2,672 (1,2); 2,667 (0.9); 2,525 (3,4);
2,511 (69,6); 2,507 (137,7); 2,503 (180,3); 2,498 (133,2); 2,494 (66,5); 2,334 (0,9); 2,330 (1,2); 2,325 (0,9); 1,857 (3,1); 1,847 (6,9); 1,838 (7,6); 1,829 (3,1); 1,586 (0,7); 1,579 (0,7); 1,286 (0,5); 1,271 (3,9); 1,262 (7,6); 1,252 (7,7); 1,242 (3,2); 1,223 (7,6); 1,205  2,511 (69.6); 2,507 (137.7); 2,503 (180,3); 2,498 (133.2); 2,494 (66.5); 2,334 (0.9); 2,330 (1.2); 2.325 (0.9); 1,857 (3,1); 1,847 (6.9); 1,838 (7.6); 1,829 (3,1); 1,586 (0.7); 1,579 (0.7); 1,286 (0.5); 1,271 (3.9); 1,262 (7.6); 1,252 (7,7); 1,242 (3,2); 1,223 (7,6); 1,205
(16,0); 1,188 (7,3); 0,146 (1,5); 0,008 (13,0); 0,000 (310,8); -0,008 (12,9); -0,150 (1,5)  (16.0); 1,188 (7.3); 0.146 (1.5); 0.008 (13.0); 0.000 (310.8); -0.008 (12.9); -0.150 (1.5)
Beispiel I-29: 1H-NMR (400,0 MHz, de-DMSO): Example I-29: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 9,801 (4,5); 9,777 (7,5); 8,876 (9,7); 8,770 (3,8); 8,165 (3,5); 8,152 (3,3); 8,149 (3,3); 8,127 (15,1); 7,817 (11,7); 7,408 (11,8);  δ = 9.801 (4.5); 9,777 (7.5); 8,876 (9.7); 8,770 (3.8); 8.165 (3.5); 8,152 (3,3); 8.149 (3.3); 8,127 (15: 1); 7,817 (11,7); 7,408 (11,8);
6,410 (0,5); 6,391 (1,8); 6,369 (2,6); 6,348 (1,9); 6,327 (0,6); 4,545 (1,8); 4,528 (5,4); 4,510 (5,4); 4,492 (1,8); 3,325 (124,8); 2,675 6.410 (0.5); 6,391 (1.8); 6.369 (2.6); 6,348 (1.9); 6,327 (0.6); 4,545 (1.8); 4,528 (5.4); 4,510 (5.4); 4,492 (1.8); 3,325 (124.8); 2,675
(1.1) ; 2,671 (1,6); 2,667 (1,2); 2,506 (178,5); 2,502 (238,7); 2,498 (184,1); 2,329 (1,5); 2,325 (1,2); 2,075 (7,4); 1,857 (3,2); 1,847 (1.1); 2,671 (1.6); 2,667 (1.2); 2,506 (178.5); 2,502 (238.7); 2,498 (184,1); 2,329 (1.5); 2.325 (1.2); 2.075 (7.4); 1,857 (3.2); 1,847
(7.3) ; 1,838 (8,1); 1,829 (3,3); 1,272 (3,5); 1,262 (7,8); 1,253 (8,0); 1,243 (3,8); 1,233 (7,9); 1,216 (16,0); 1,198 (7,5); 0,000 (3,7)  (7.3); 1,838 (8.1); 1,829 (3.3); 1,272 (3.5); 1,262 (7,8); 1,253 (8.0); 1,243 (3.8); 1,233 (7.9); 1,216 (16,0); 1.198 (7.5); 0,000 (3,7)
Beispiel I-30: 1H-NMR (400,0 MHz, de-DMSO): Example I-30: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 10,464 (3,7); 10,439 (4,0); 9,761 (4,2); 8,923 (9,7); 8,861 (4,3); 8,429 (3,4); 8,414 (3,3); 8,317 (0,4); 8,240 (16,0); 8,223 (2,6);  δ = 10.464 (3.7); 10.439 (4.0); 9,761 (4,2); 8,923 (9.7); 8,861 (4,3); 8.429 (3.4); 8.414 (3.3); 8.317 (0.4); 8,240 (16,0); 8.223 (2.6);
8,072 (0,5); 8,009 (13,1); 7,850 (0,4); 7,673 (2,6); 7,648 (3,8); 7,625 (2,5); 6,396 (0,5); 6,376 (1,7); 6,354 (2,6); 6,332 (1,8); 6,311 (0,5); 4,627 (2,0); 4,610 (5,7); 4,592 (5,8); 4,575 (2,0); 3,329 (286,3); 2,672 (1,7); 2,668 (1,4); 2,507 (207,0); 2,503 (266,8); 2,499 (207,6); 2,330 (1,7); 2,326 (1,3); 2,076 (3,7); 1,866 (3,2); 1,856 (7,5); 1,847 (8,2); 1,838 (3,6); 1,330 (7,8); 1,313 (16,0); 1,294 (8,9); 8,072 (0.5); 8,009 (13.1); 7,850 (0.4); 7.673 (2.6); 7,648 (3.8); 7.625 (2.5); 6.396 (0.5); 6.376 (1.7); 6,354 (2,6); 6.332 (1.8); 6.311 (0.5); 4,627 (2.0); 4,610 (5.7); 4,592 (5.8); 4,575 (2.0); 3,329 (286.3); 2,672 (1.7); 2,668 (1.4); 2,507 (207,0); 2,503 (266,8); 2,499 (207.6); 2.330 (1.7); 2,326 (1.3); 2.076 (3.7); 1,866 (3.2); 1,856 (7.5); 1,847 (8.2); 1,838 (3.6); 1,330 (7.8); 1,313 (16.0); 1,294 (8.9);
1,280 (8,3); 1,271 (8,1); 1,261 (3,4); 0,146 (0,7); 0,000 (138,4); -0,149 (0,7) 1,280 (8.3); 1,271 (8,1); 1,261 (3,4); 0.146 (0.7); 0,000 (138.4); -0.149 (0.7)
Beispiel 1-31: 1H-NMR (400,0 MHz, de-DMSO): Example 1-31: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 9,793 (2,5); 9,770 (4,0); 8,876 (5,2); 8,776 (2,0); 8,316 (0,5); 8,121 (8,8); 7,974 (0,9); 7,958 (1,0); 7,951 (1,0); 7,941 (0,9); 7,816 δ = 9.793 (2.5); 9,770 (4.0); 8,876 (5.2); 8.776 (2.0); 8.316 (0.5); 8,121 (8,8); 7.974 (0.9); 7.958 (1.0); 7.951 (1.0); 7.941 (0.9); 7.816
(6.4) ; 7,407 (6,4); 6,400 (0,9); 6,378 (1,3); 6,357 (1,0); 4,547 (0,9); 4,529 (2,6); 4,511 (2,6); 4,493 (0,9); 3,328 (149,6); 2,690 (16,0); 2,681 (0,5); 2,676 (0,8); 2,672 (1,0); 2,667 (0,7); 2,663 (0,4); 2,525 (2,4); 2,520 (3,8); 2,511 (53,7); 2,507 (109,4); 2,503 (145,0); (6.4); 7,407 (6.4); 6,400 (0.9); 6.378 (1.3); 6.357 (1.0); 4,547 (0.9); 4,529 (2,6); 4,511 (2,6); 4.493 (0.9); 3,328 (149.6); 2,690 (16.0); 2,681 (0.5); 2,676 (0.8); 2,672 (1.0); 2,667 (0.7); 2,663 (0.4); 2,525 (2,4); 2,520 (3.8); 2,511 (53.7); 2,507 (109.4); 2,503 (145.0);
2,498 (106,4); 2,494 (52,3); 2,334 (0,7); 2,329 (0,9); 2,325 (0,7); 1,858 (1,8); 1,848 (4,0); 1,839 (4,4); 1,829 (1,8); 1,398 (4,0); 1,272 2,498 (106.4); 2,494 (52.3); 2.334 (0.7); 2,329 (0.9); 2.325 (0.7); 1,858 (1.8); 1,848 (4.0); 1,839 (4.4); 1,829 (1.8); 1,398 (4.0); 1,272
(1.9) ; 1,262 (4,3); 1,253 (4,4); 1,242 (2,1); 1,233 (4,5); 1,216 (9,0); 1,198 (4,1); 0,146 (1,2); 0,008 (9,0); 0,000 (251,3); -0,009 (9,9); -(1.9); 1,262 (4,3); 1,253 (4.4); 1,242 (2,1); 1,233 (4,5); 1,216 (9.0); 1,198 (4,1); 0.146 (1.2); 0.008 (9.0); 0,000 (251.3); -0.009 (9.9); -
0,150 (1,1) 0.150 (1.1)
Beispiel I-32: 1H-NMR (400,0 MHz, de-DMSO): Example I-32: 1 H-NMR (400.0 MHz, de-DMSO):
δ= 9,769 (3,6); 9,489 (4,2); 9,466 (4,4); 8,868 (9,5); 8,781 (3,6); 8,317 (0,4); 8,109 (15,9); 8,100 (0,6); 8,076 (3,3); 8,059 (3,2); 7,999 (1,6); 7,994 (1,7); 7,988 (1,9); 7,979 (2,2); 7,973 (1,9); 7,966 (1,9); 7,829 (0,7); 7,783 (11,7); 7,697 (0,9); 7,632 (2,7); 7,606 (3,5);  δ = 9.769 (3.6); 9,489 (4,2); 9,466 (4,4); 8,868 (9.5); 8,781 (3.6); 8.317 (0.4); 8,109 (15,9); 8,100 (0.6); 8.076 (3.3); 8,059 (3.2); 7,999 (1.6); 7.994 (1.7); 7,988 (1.9); 7.979 (2.2); 7,973 (1.9); 7.966 (1.9); 7.829 (0.7); 7,783 (11,7); 7.697 (0.9); 7,632 (2.7); 7.606 (3.5);
7,584 (2,5); 7,336 (11,8); 6,562 (1,1); 6,552 (1,0); 6,425 (2,2); 6,414 (2,2); 6,287 (1,1); 6,276 (1,2); 5,769 (0,5); 5,757 (3,8); 5,746 (0,7); 5,736 (1,4); 5,726 (1,1); 5,714 (1,1); 5,702 (1,4); 5,691 (0,7); 5,678 (0,6); 5,669 (0,5); 4,541 (1,8); 4,524 (5,0); 4,506 (5,0);  7,584 (2.5); 7.336 (11.8); 6.562 (1.1); 6,552 (1.0); 6.425 (2.2); 6.414 (2.2); 6.287 (1.1); 6.276 (1.2); 5,769 (0.5); 5,757 (3.8); 5,746 (0.7); 5,736 (1.4); 5,726 (1.1); 5,714 (1.1); 5,702 (1.4); 5.691 (0.7); 5,678 (0.6); 5.669 (0.5); 4,541 (1.8); 4,524 (5.0); 4,506 (5.0);
4,488 (1,8); 4,038 (0,5); 4,020 (0,5); 3,331 (173,5); 3,030 (2,2); 2,774 (1,9); 2,677 (0,7); 2,672 (1,0); 2,668 (0,8); 2,525 (2,5); 2,520 (3,9); 2,512 (55,0); 2,507 (111,8); 2,503 (148,3); 2,498 (109,8); 2,494 (54,5); 2,334 (0,7); 2,330 (1,0); 2,325 (0,7); 2,087 (15,4); 1,989 (2,0); 1,858 (3,2); 1,848 (7,3); 1,839 (7,8); 1,829 (3,2); 1,272 (3,4); 1,262 (7,7); 1,253 (7,8); 1,242 (3,5); 1,215(7,6); 1,198(16,0);  4,488 (1.8); 4.038 (0.5); 4,020 (0.5); 3,331 (173.5); 3.030 (2.2); 2,774 (1.9); 2,677 (0.7); 2,672 (1.0); 2,668 (0.8); 2,525 (2.5); 2,520 (3.9); 2,512 (55.0); 2,507 (111,8); 2,503 (148,3); 2,498 (109.8); 2,494 (54.5); 2.334 (0.7); 2,330 (1.0); 2.325 (0.7); 2,087 (15.4); 1,989 (2.0); 1,858 (3.2); 1,848 (7.3); 1,839 (7.8); 1,829 (3.2); 1,272 (3,4); 1,262 (7,7); 1,253 (7,8); 1,242 (3.5); 1.215 (7.6); 1,198 (16.0);
1,180 (7,3); 1,158 (0,7); 1,141 (0,5); 0,146 (1,3); 0,008 (9,8); 0,000 (266,0); -0,009 (10,6); -0,150 (1,3) a) Die Bestimmung des M+ mit der LC-MS im sauren Bereich erfolgt bei pH 2,7 Acetonitril (enthält 0,1% Ameisensäure) und Wasser als Eluenten; linearer Gradient von 10% Acetonitril bis 95% Acetonitril Gerät: Agilent 1100 LC-System, Agilent MSD System, HTS PAL. Die Bestimmung der in den vorangegangenen Tabellen und Herstellungsbeispielen angegebenen logP- Werte erfolgte gemäß EEC Directive 79/831 Annex V.A8 durch HPLC (High Performance Liquid Chromatography) an einer Phasenumkehrsäule (C18). Temperatur 43 °C. Die Eichung erfolgt mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP Werte bekannt sind. b) Die Bestimmung der 'H-NMR-Daten erfolgt mit einem Bruker Avance 400 ausgestattet mit einem Durchflussprobenkopf (60 μΐ Volumen), mit Tetramethylsilan als Referenz (0.0) und den Lösungsmitteln CD3CN, CDC13, D6-DMSO. 1,180 (7.3); 1.158 (0.7); 1.141 (0.5); 0.146 (1.3); 0.008 (9.8); 0,000 (266,0); -0.009 (10.6); -0.150 (1.3) a) The determination of M + with the LC-MS in the acidic range is carried out at pH 2.7 acetonitrile (contains 0.1% formic acid) and water as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile Device: Agilent 1100 LC system, Agilent MSD system, HTS PAL. The determination of the logP values given in the preceding tables and preparation examples was carried out according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion column (C18). Temperature 43 ° C. The calibration is carried out with unbranched alkan-2-ones (having 3 to 16 carbon atoms) whose logP values are known. b) The determination of the 'H-NMR data is carried out with a Bruker Avance 400 equipped with a flow probe head (60 μΐ volume), with tetramethylsilane as reference (0.0) and the solvents CD 3 CN, CDC1 3 , D 6 -DMSO.
Die NMR-Daten ausgewählter Beispiele werden entweder in klassischer Form (δ-Werte, Multiplettaufspaltung, Anzahl der H-Atome) oder als NMR-Peak-Listen aufgeführt. NMR-Peak-Listenverfahren The NMR data of selected examples are listed either in classical form (δ values, multiplet splitting, number of H atoms) or as NMR peak lists. NMR peak list procedures
Die 1 H-NMR-Daten ausgewählter Beispiele werden in Form von 1H-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der δ-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die δ-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines Beispieles hat daher die Form: δι (Intensität^; 82 (Intensität2); ; δ; (Intensität^; ; δη (Intensitätn) The 1 H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ-value signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of an example therefore has the form: δι (intensity ^; 82 (intensity 2);; δ; (intensity ^;; δ η (intensity n )
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
Zur Kalibrierung der chemischen Verschiebung von 1 H-NMR- Spektren wird Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels benutzt, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der 'H-NMR-Peaks sind ähnlich den klassischen 'H-NMR-Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. To calibrate the chemical shift of 1 H-NMR spectra, tetramethylsilane and / or the chemical shift of the solvent is used, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to. The lists of the 'H NMR peaks are similar to the classical' H NMR prints and thus usually contain all the peaks listed in a classical NMR interpretation.
Darüber hinaus können sie wie klassische 'H-NMR-Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von 'H-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90 %). In addition, they can, like classic 'H-NMR prints solvent signals, signals from stereoisomers of the target compounds, which are also the subject of the invention, and / or show peaks of impurities. When indicating compound signals in the delta range of solvents and / or water, our lists of 'H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D6 and the peak of water, which are usually in the Average high intensity. The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrucken" zu erkennen. Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help to detect the reproduction of our manufacturing process by "by-product fingerprints."
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 'H-NMR- Interpretation. An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can isolate the peaks of the target compounds as needed, using additional intensity filters, if necessary. This isolation would be similar to peak picking in classical 'H NMR interpretation.
Weitere Details zu 'H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on 'H NMR peaks can be found in Research Disclosure Database Number 564025.
Anwendungsbeispiele applications
Die folgenden Beispiele zeigen die msektizide und akarizide Wirkung der erfindungsgemäßen Verbindungen. Dabei beziehen sich die genannten erfindungsgemäßen Verbindungen auf die in der Tabelle 1 mit den entsprechenden Referenzzeichen (Nr.) aufgeführten Verbindungen: Amblyomma hebaraeum -Test The following examples show the insecticidal and acaricidal activity of the compounds according to the invention. In this case, the compounds according to the invention refer to the compounds listed in Table 1 with the corresponding reference signs (No.): Amblyomma hebaraeum test
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Zeckennymphen {Amblyomma hebraeum) werden in perforierte Plastikbecher gesetzt und in der gewünschten Konzentration eine Minute getaucht. Die Zecken werden auf Filterpapier in eine Petrischale überführt und in einem Klimaschrank gelagert. Tick nymphs (Amblyomma hebraeum) are placed in perforated plastic cups and dipped for one minute at the desired concentration. The ticks are transferred to filter paper in a Petri dish and stored in a climate cabinet.
Nach 42 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Zecken abgetötet wurden; 0 % bedeutet, dass keine der Zecken abgetötet wurde. After 42 days the kill is determined in%. 100% means that all ticks have been killed; 0% means that none of the ticks have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von lOOppm: 1-30. In this test, z. Example, the following compounds of the preparation examples an effect of 100% at a rate of lOOppm: 1-30.
Boophilus microplus -Injektionstest (BOOPMI Inj) Boophilus microplus injection test (BOOPMI Inj)
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Lösungsmittel und verdünnt das Konzentrat mit Lösungsmittel auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.
Ι μΐ der Wirkstofflösung wird in das Abdomen von 5 vollgesogenen, adulten, weiblichen Rinderzecken (Boophilus microplus) injiziert. Die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. Ι μΐ of the drug solution is injected into the abdomen of 5 adult, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 20μg/Tier: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08, 1-09, I- 10, 1-11, 1-12, 1-13, 1-16, 1-17, 1-18, 1-19, 1-20, , 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31 , 1- 32. Boophilus microplus - Diptest The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile. In this test, for example, the following compounds of the preparation examples show an effect of 100% at an application rate of 20 μg / animal: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08 , 1-09, I-10, 1-11, 1-12, 1-13, 1-16, 1-17, 1-18, 1-19, 1-20, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31, 1-32. Boophilus microplus - Diptest
Testtiere: Rinderzecken {Boophilus microplus) Stamm Parkhurst, SP-resistent Test Animals: Beef Ticks {Boophilus microplus) strain Parkhurst, SP resistant
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
10 mg Wirkstoff werden in 0,5 ml Dimethylsulfoxid gelöst. Zwecks Herstellung einer geeigneten Formulierung verdünnt man die Wirkstofflösung mit Wasser auf die jeweils gewünschte Konzentration. 10 mg of active ingredient are dissolved in 0.5 ml of dimethyl sulfoxide. In order to prepare a suitable formulation, the active compound solution is diluted with water to the particular desired concentration.
Diese Wirkstoffzubereitung wird in Röhrchen pipettiert. 8-10 gesogene, adulte, weibliche Rinderzecken {Boophilus microplus) werden in ein weiteres Röhrchen mit Löchern überführt. Das Röhrchen wird in die Wirkstoffzubereitung getaucht wobei alle Zecken vollständig benetzt werden. Nach Ablaufen der Flüssigkeit werden die Zecken auf Filterscheiben in Kunststoffschalen überführt und in einem klimatisierten Raum aufbewahrt. This preparation of active compound is pipetted into tubes. 8-10 sucked, adult, female cattle ticks (Boophilus microplus) are transferred to another tube with holes. The tube is dipped into the preparation of the active ingredient with all ticks being completely wetted. After draining the liquid, the ticks are transferred to filter discs in plastic trays and stored in an air conditioned room.
Die Wirkungskontrolle erfolgt nach 7 Tagen auf Ablage fertiler Eier. Eier, deren Fertilität nicht äußerlich sichtbar ist, werden bis zum Larvenschlupf nach etwa 42 Tagen im Klimaschrank aufbewahrt. Eine Wirkung von 100 % bedeutet, dass keine der Zecken fertile Eier gelegt hat, 0% bedeutet, dass alle Eier fertil sind. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 20ppm: 1-30. The effect control takes place after 7 days on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile. In this test, e.g. the following compounds of the preparation examples have an effect of 100% at an application rate of 20 ppm: 1-30.
Ctenocephalides felis - Oraltest (CTECFE) Ctenocephalides felis - Oral test (CTECFE)
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zwecks Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid. Durch Verdünnen mit citriertem Rinderblut erhält man die gewünschte Konzentration. For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration.
Ca. 20 nüchterne adulte Katzenflöhe (Ctenocephalides felis) werden in eine Kammer eingesetzt, die oben und unten mit Gaze verschlossen ist. Auf die Kammer wird ein Metallzylinder gestellt, dessen Unterseite mit Parafilm verschlossen ist. Der Zylinder enthält die Blut- Wirkstoffzubereitung, die von den Flöhen durch die Parafilmmembran aufgenommen werden kann. Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Flöhe abgetötet wurden; 0 % bedeutet, dass keiner der Flöhe abgetötet wurde. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane. After 2 days the kill is determined in%. 100% means> that all fleas have been killed; 0% means that none of the fleas have been killed.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von lOOppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08, 1-09, 1-10, 1-11, 1-12, 1-13, 1-16, 1-17, 1-18, 1-19, 1-20, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31, 1-32. In this test, e.g. the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 ppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08, 1-09, 1- 10, 1-11, 1-12, 1-13, 1-16, 1-17, 1-18, 1-19, 1-20, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31, 1-32.
Lucilla cuprina - Test (LUCICU) Lucilla cuprina - test (LUCICU)
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. Ca. 20 LI -Larven der Australischen Schafgoldfliege (Lucilla cuprina) werden in ein Testgefäß überführt, welches gehacktes Pferdefleisch und die Wirkstoffzubereitung der gewünschten Konzentration enthält. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration. Approximately Twenty LI larvae of the Australian Goldfish fly (Lucilla cuprina) are transferred to a test vessel containing chopped horse meat and the preparation of active compound of the desired concentration.
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von lOOppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08, 1-09, 1-10, 1-12, 1-13, 1-16, 1-18, 1-19, 1-20, 1-22, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31, 1-32. After 2 days the kill is determined in%. 100% means> that all larvae have been killed; 0% means that no larvae have been killed. In this test, e.g. the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 ppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-08, 1-09, 1- 10, 1-12, 1-13, 1-16, 1-18, 1-19, 1-20, 1-22, 1-24, 1-25, 1-26, 1-27, 1-29, 1-30, 1-31, 1-32.
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von lOOppm: 1-17, 1-23. Musca domestica-Test (MUSCDO) In this test, e.g. the following compounds of the preparation examples an effect of 90% at a rate of lOOppm: 1-17, 1-23. Musca domestica test (MUSCDO)
Lösungsmittel: Dimethylsulfoxid Solvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
Gefäße, die einen Schwamm enthalten, der mit Zuckerlösung und der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit 10 adulten Stubenfliegen (Musca domestica) besetzt. Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
Nach 2 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Fliegen abgetötet wurden; 0 % bedeutet, dass keine der Fliegen abgetötet wurde. Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von lOOppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-09, 1-10, 1-12, 1-13, 1-16, 1-18, 1-19, 1-20, 1-22, 1-26, 1-27, 1-29, 1-30, 1-31. After 2 days the kill is determined in%. 100% means> that all flies have been killed; 0% means that none of the flies have been killed. In this test, for example, the following compounds of the preparation examples show an effect of 100% at a rate of 100 ppm: 1-01, 1-02, 1-03, 1-04, 1-05, 1-07, 1-09, 1 -10, 1-12, 1-13, 1-16, 1-18, 1-19, 1-20, 1-22, 1-26, 1-27, 1-29, 1-30, 1-31 ,
Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von lOOppm: 1-17, 1-24. In this test, e.g. the following compounds of the preparation examples an effect of 80% at a rate of lOOppm: 1-17, 1-24.
Meloidogyne incognita- Test Meloidogyne incognita test
Lösungsmittel: 125,0 Gewichtsteile Aceton Solvent: 125.0 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration. To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße werden mit Sand, Wirkstofflösung, einer Ei-Larven-Suspension des südlichen Wurzelgallenälchens {Meloidogyne incognita) und Salatsamen gefüllt. Die Salatsamen keimen und die Pflänzchen entwickeln sich. An den Wurzeln entwickeln sich die Gallen. Vessels are filled with sand, drug solution, an egg larvae suspension of the southern root gallbladder (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.
Nach 14 Tagen wird die nematizide Wirkung anhand der Gallenbildung in % bestimmt. Dabei bedeutet 100 %>, dass keine Gallen gefunden wurden; 0 %> bedeutet, dass die Zahl der Gallen an den behandelten Pflanzen der unbehandelten Kontrolle entspricht. After 14 days, the nematicidal activity is determined on the basis of bile formation in%. 100% means that no bile was found; 0%> means that the number of bile on the treated plants corresponds to the untreated control.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90%) bei einer Aufwandmenge von 20ppm: 1-19. In this test, z. Example, the following compounds of the preparation examples effect of 90%) at a rate of 20 ppm: 1-19.
Myzus persicae - Sprühtest Lösungsmittel: 78 Gewichtsteile Aceton Myzus persicae - Spray Test Solvent: 78 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether  Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfirsichblattlaus {Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %>, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden. Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid {Myzus persicae) are sprayed with an active compound preparation of the desired concentration. After 6 days, the effect is determined in%. 100% means> that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: 1-29. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 90% bei einer Aufwandmenge von 100g/ha: 1-20, 1-32. In this test, z. Example, the following compounds of the preparation examples effect of 100% at an application rate of 100g / ha: 1-29. In this test, z. For example, the following compounds of the Preparation Examples Effect of 90% at a rate of 100g / ha: 1-20, 1-32.
Phaedon cochleariae - Sprühtest (PHAECO) Phaedon cochleariae - spray test (PHAECO)
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid Emulgator: Alkylarylpolyglykolether 1.5 parts by weight of dimethylformamide emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Chinakohlblattscheiben (Brassica pekinensis) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Larven des Meerrettichblattkäfers (Phaedon cochleariae) besetzt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %>, dass alle Käferlarven abgetötet wurden; 0 %> bedeutet, dass keine Käferlarven abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1-08, 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1- 30, 1-31, 1-32. After 7 days, the effect is determined in%. 100% means> that all beetle larvae have been killed; 0%> means that no beetle larvae have been killed. In this test, z. For example, the following compounds of Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1-08 , 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1 -22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100%) bei einer Aufwandmenge von 20g/ha: 1-15. In this test, z. B. the following compounds of the preparation examples effect of 100%) at a rate of 20g / ha: 1-15.
Spodoptera frugiperda - Sprühtest (SPODFR) Spodoptera frugiperda - spray test (SPODFR)
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid Emulgator: Alkylarylpolyglykolether 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms (Spodoptera frugiperda) besetzt. Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
Nach 7 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %>, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde. After 7 days, the effect is determined in%. 100% means> that all caterpillars have been killed; 0% means that no caterpillar has been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 100% bei einer Aufwandmenge von 100g/ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1-08, 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1- 30, 1-31, 1-32. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele Wirkung von 83% bei einer Aufwandmenge von 100g/ha: 1-23. In this test, z. For example, the following compounds of Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-02, 1-03, 1-04, 1-05, 1-06, 1-07, 1-08 , 1-09, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1 -21, 1-22, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32. In this test, z. Example, the following compounds of the preparation examples effect of 83% at a rate of 100g / ha: 1-23.
Tetranychus urticae - Sprühtest, OP-resistent (TETRUR) Tetranychus urticae - spray test, surgical-resistant (TETRUR)
Lösungsmittel: 78,0 GewichtsteileAceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid Emulgator : Alkylarylpolyglykolether 1.5 parts by weight of dimethylformamide emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
Nach 6 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %>, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100g/ha: 1-01 , 1-02, 1-04, 1-06, 1-07, 1-08, 1-09, 1-10, 1-11, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-30, 1-31, 1-32. After 6 days, the effect is determined in%. 100%> means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 100% at a rate of 100 g / ha: 1-01, 1-02, 1-04, 1-06, 1-07, 1-08, 1-09, 1- 10, 1-11, 1-13, 1-14, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-30, 1-31, 1-32.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90% bei einer Aufwandmenge von 100g/ha: 1-03, 1-05, 1-15, 1-29. In this test, z. For example, the following compounds of the Preparation Examples have an effect of 90% at a rate of 100 g / ha: 1-03, 1-05, 1-15, 1-29.
Spodoptera frugiperda - Sprühtest (SPODFR) Spodoptera frugiperda - spray test (SPODFR)
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt.  Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water which contains an emulsifier concentration of 1000 ppm until the desired concentration is reached. To prepare further test concentrations, dilute with emulsifier-containing water.
Maisblattscheiben (Zea mays) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt und nach dem Abtrocknen mit Raupen des Heerwurms {Spodoptera frugiperda) besetzt. Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm {Spodoptera frugiperda).
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %>, dass alle Raupen abgetötet wurden; 0 % bedeutet, dass keine Raupe abgetötet wurde. After the desired time, the effect is determined in%. 100% means> that all caterpillars have been killed; 0% means that no caterpillar has been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle 2. In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: see Table 2.
Frankliniella occidentalis - Sprühtest (FRANOC) Frankliniella occidentalis - Spray Test (FRANOC)
Lösungsmittel: 7 Gewichtsteile Dimethylformamid Solvent: 7 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether  Emulsifier: alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bei erforderlicher Zugabe von Ammoniumsalzen oder/und Penetrationsförderern werden diese jeweils in einer Konzentration von 1000 ppm der Präparatelösung zugefügt. Buschbohnenpflanzen (Phaseolus vulgaris) werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Nach Abtrocknung werden die behandelten Pflanzen mit einer gemischten Thripspopulation (Frankliniella occidentalis) infiziert. To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. When necessary addition of ammonium salts or / and penetration promoters they are added in each case in a concentration of 1000 ppm of the preparation solution. Bush bean plants (Phaseolus vulgaris) are sprayed with an active compound preparation of the desired concentration. After drying, the treated plants are infected with a mixed thrip population (Frankliniella occidentalis).
Nach der gewünschten Zeit wird die pflanzenschützende Wirkung in % bestimmt. Dabei bedeutet 100 %, dass kein Schaden zu sehen ist; 0 % bedeutet, dass der Schaden an der behandelten Pflanze dem der unbehandelten Kontrolle entspricht. After the desired time, the phytosanitary effect is determined in%. 100% means that no damage can be seen; 0% means that the damage to the treated plant matches that of the untreated control.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle 2. In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: see Table 2.
Diabrotica balteata - Drenchtest (DIABBA) Lösungsmittel: 7 Gewichtsteile Dimethylformamid Diabrotica balteata - Drench test (DIABBA) Solvent: 7 parts by weight of dimethylformamide
Emulgator: 2 Gewichtsteile Alkylarylpolyglykolether  Emulsifier: 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration, wobei das Erdvolumen in das gedrencht wird, mitberücksichtigt werden muss. Es ist darauf zu achten, dass in der Erde eine Konzentration von 40 ppm Emulgator nicht überschritten wird. Zur Herstellung weiterer Testkonzentrationen wird mit Wasser verdünnt. To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, whereby the volume of the earth is forced into the vessel. It must be ensured that a concentration of 40 ppm emulsifier is not exceeded in the soil. To prepare further test concentrations, it is diluted with water.
Jeweils 5 Maiskörner werden in mit Erde gefüllte Töpfe ausgesät (Zea mays) und am darauffolgenden Tag mit der Wirkstoffzubereitung der gewünschten Konzentration angegossen. Nach einem Tag werden 25 L2-Larven des Maiswurzelbohrers {Diabrotica balteata) hinzugegeben. In each case 5 corn kernels are seeded in pots filled with soil (Zea mays) and poured on the following day with the preparation of active compound of the desired concentration. After one day, 25 L2 larvae of the corn rootworm {Diabrotica balteata) are added.
Nach 8 Tagen wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle 5 Pflanzen gekeimt und gewachsen sind; 0 % bedeutet, dass keine Pflanze aufgelaufen ist. After 8 days, the effect is determined in%. 100% means that all 5 plants have germinated and grown; 0% means that no plant has accumulated.
Bei diesem Test zeigt z. B. die folgende Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle 2. In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: see Table 2.
Tetranychus urticae - Sprühtest ; OP-resistent (TETRUR) Tetranychus urticae - spray test; OP-resistant (TETRUR)
Lösungsmittel: 78,0 Gewichtsteile Aceton Solvent: 78.0 parts by weight of acetone
1,5 Gewichtsteile Dimethylformamid  1.5 parts by weight of dimethylformamide
Emulgator: Alkylarylpolyglykolether Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung löst man 1 Gewichtsteil Wirkstoff mit den angegebenen Gewichtsteilen Lösungsmittel und füllt mit Wasser, welches eine Emulgatorkonzentration von 1000 ppm enthält, bis zum Erreichen der gewünschten Konzentration auf. Zur Herstellung weiterer Testkonzentrationen wird mit emulgatorhaltigem Wasser verdünnt. Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt. Emulsifier: alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water. Bean leaf discs (Phaseolus vulgaris) infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden. Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele überlegene Wirksamkeit gegenüber dem Stand der Technik: siehe Tabelle 2. After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed. In this test, z. For example, the following compounds of Preparation Examples have superior efficacy over the prior art: see Table 2.
Tabelle 2: Table 2:
Substanz Tierart Konzentration % Wirkung dat a) Substance species concentration% effect dat a)
SPODFR 4 g/ha 100 7dat SPODFR 4 g / ha 100 7dat
SPODFR 0.8 g/ha 33 7dat  SPODFR 0.8 g / ha 33 7dat
FPvANOC 4 ppm 98 7dat FPvANOC 4 ppm 98 7dat
FPvANOC 0.8 ppm 60 7dat FPvANOC 0.8 ppm 60 7dat
Stand der Technik State of the art
DIABBA 20 ppm 60 8dat DIABBA 20 ppm 60 8dat
Verbindung Nr. 273 WO-A-2012/119984 Compound No. 273 WO-A-2012/119984
DIABBA 4 ppm 0 8dat DIABBA 4 ppm 0 8dat
TETRUR 20 g/ha 100 6datTETRUR 20 g / ha 100 6dat
TETRUR 4 g/ha 70 6dat TETRUR 4 g / ha 70 6dat
Bsp.-Nr. 1-01 SPODFR 4 g/ha 100 7dat Expl 1-01 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfmdungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-02 SPODFR 4 g/ha 100 7dat Expl 1-02 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfmdungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-03 SPODFR 4 g/ha 100 7dat Expl 1-03 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfmdungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-04 SPODFR 4 g/ha 100 7dat Expl 1-04 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-06 SPODFR 4 g/ha 100 7dat Expl 1-06 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-07 SPODFR 4 g/ha 100 7dat Expl 1-07 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 67 7dat ernndungsgemäß  SPODFR 0.8 g / ha 67 7dat according to the invention
Bsp.-Nr. 1-08 SPODFR 4 g/ha 100 7dat Expl 1-08 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß Substanz Tierart Konzentration % Wirkung dat a) SPODFR 0.8 g / ha 100 7dat according to the invention Substance species concentration% effect dat a)
Bsp.-Nr. 1-10 SPODFR 4 g/ha 100 7dat Expl 1-10 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-12 SPODFR 4 g/ha 100 7dat Expl 1-12 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-15 SPODFR 4 g/ha 100 7dat Expl 1-15 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 83 7dat erfindungsgemäß  SPODFR 0.8 g / ha 83 7dat according to the invention
Bsp.-Nr. 1-16 FRANOC 4 ppm 90 7dat Expl 1-16 FRANOC 4 ppm 90 7dat
FRANOC 0.8 ppm 90 7dat ernndungsgemäß  FRANOC 0.8 ppm 90 7dat according to the instructions
DIABBA 20 ppm 100 8dat DIABBA 20 ppm 100 8dat
DIABBA 4 ppm 50 8dat DIABBA 4 ppm 50 8dat
Bsp.-Nr. 1-18 SPODFR 4 g/ha 100 7dat Expl 1-18 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-19 DIABBA 20 ppm 100 8dat ernndungsgemäß Expl 1-19 DIABBA 20 ppm 100 8dat according to the instructions
Bsp.-Nr. 1-20 SPODFR 4 g/ha 100 7dat Expl 1-20 SPODFR 4g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-21 SPODFR 4 g/ha 100 7dat Expl 1-21 SPODFR 4 g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
Bsp.-Nr. 1-22 SPODFR 4 g/ha 100 7dat Expl 1-22 SPODFR 4 g / ha 100 7dat
SPODFR 0.8 g/ha 100 7dat erfindungsgemäß  SPODFR 0.8 g / ha 100 7dat according to the invention
TETRUR 20 g/ha 100 6dat TETRUR 20 g / ha 100 6dat
TETRUR 4 g/ha 100 6datTETRUR 4 g / ha 100 6dat
DIABBA 20 ppm 100 8dat Substanz Tierart Konzentration % Wirkung dat a) DIABBA 20 ppm 100 8dat Substance species concentration% effect dat a)
DIABBA 4 ppm 50 8dat a) Abkürzungen: dat = days after treatment;  DIABBA 4 ppm 50 8dat a) Abbreviations: dat = days after treatment;
Die Tabelle zeigt, dass die erfindungsgemäßen Verbindungen eine überlegene biologische Wirksamkeit gegenüber der aus WO-A-2012/119984 bekannten Verbindung Nr. 273 insbesondere bei niedrigen aufgewendeten Konzentrationen aufweisen. Dies wird insbesondere deutlich beim Vergleich der Verbindung Nr. 273 der WO-A-2012/119984 und der erfindungsgemäßen Verbindungen Nr. 1-03 und 1-07, die sich ausschließlich darin von Verbindung Nr. 273 der WO-A-2012/119984 unterscheiden, dass die erfindungsgemäßen Verbindungen zusätzlich eine Substitution mit R1 = F (Verbindung Nr. 1-03) bzw. R1 = Cl (Verbindung Nr. 1-07) in Position 4 am Phenylring aufweisen. Der Vergleich der biologischen Wirksamkeiten zeigt die Überlegenheit der neu gefundenen Gruppe von Verbindungen. The table shows that the compounds according to the invention have a superior biological activity compared to the compound no. 273 known from WO-A-2012/119984, in particular at low concentrations used. This becomes particularly clear when comparing Compound No. 273 of WO-A-2012/119984 and Compounds Nos. 1-03 and 1-07 of the invention, which are exclusively disclosed in Compound No. 273 of WO-A-2012/119984 distinguish that the compounds according to the invention additionally have a substitution with R 1 = F (compound Nos. 1-03) and R 1 = Cl (compound Nos. 1-07) in position 4 on the phenyl ring. The comparison of the biological activities shows the superiority of the newly found group of compounds.
Analoges gilt auch für den Vergleich der Verbindung Nr. 273 der WO-A-2012/119984 und der erfindungsgemäßen Verbindungen Nr. 1-10 und 1-22, die sich ausschließlich darin unterscheiden, dass die erfindungsgemäßen Verbindungen am Phenylring neben einer Substitution mit -CF3 noch eine Substitution mit Halogen aufweisen. Analoges gilt auch für den Vergleich der Verbindung Nr. 273 der WO-A-2012/119984 und der erfindungsgemäßen Verbindungen Nr. 1-16 und 1-19, die sich ausschließlich darin unterscheiden, dass die erfindungsgemäßen Verbindungen zusätzlich eine Substitution mit R1 = Cl in Position 4 am Phenylring aufweisen und in denen R4 nicht Ethyl ist sondern Methyl (Verbindung Nr. 1-16) bzw. Prop-2-in-l-yl (Verbindung Nr. 1-19). The same applies to the comparison of compound no. 273 of WO-A-2012/119984 and the inventive compounds Nos. 1-10 and 1-22, which differ only in that the compounds of the invention on the phenyl ring in addition to a substitution with - CF3 still have a substitution with halogen. The same applies analogously to the comparison of compound no. 273 of WO-A-2012/119984 and inventive compounds no. 1-16 and 1-19, which differ solely in that the compounds according to the invention additionally have a substitution with R 1 = Have Cl in position 4 on the phenyl ring and in which R 4 is not ethyl but methyl (compound Nos. 1-16) and prop-2-yn-1-yl (compound Nos. 1-19).

Claims

Patentansprüche claims
1. Verbindungen der allgemeinen Formel (I), 1. Compounds of the general formula (I)
wobei  in which
R1 für Cyano, Fluor, Chlor, Brom, lod, Difluormethyl, Dichlorfluormethyl, Chlordifluormethyl, Trifluormethyl, Pentafluorethyl, Chlortetrafluorethyl, Difluormethoxy, Trifluormethoxy steht, wobei mindestens ein Substituent R1 für Fluor, Chlor, Brom oder lod steht, R2 für Fluor, Trifluormethyl oder Wasserstoff steht, n für 2, 3, 4 oder 5 steht R 1 is cyano, fluorine, chlorine, bromine, iodine, difluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, trifluoromethyl, pentafluoroethyl, chlorotetrafluoroethyl, difluoromethoxy, trifluoromethoxy, where at least one substituent R 1 is fluorine, chlorine, bromine or iodine, R 2 is fluorine , Trifluoromethyl or hydrogen, n is 2, 3, 4 or 5
R3 für Wasserstoff steht, R 3 is hydrogen,
R4 für Wasserstoff, Methyl, Ethyl, Prop-l-yl, Prop-2-en-l -yl, Prop-2-in-l-yl, Ethenyl, R 4 is hydrogen, methyl, ethyl, prop-1-yl, prop-2-en-1-yl, prop-2-yn-1-yl, ethenyl,
But-2-in-l-yl steht,  But-2-in-1-yl is
G für CH oder N steht, G is CH or N,
R6 für Cyano, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl oder Trifluormethyl steht, sowie Salze und N-Oxide von Verbindungen der Formel (I). R 6 is cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl or trifluoromethyl, and salts and N-oxides of compounds of the formula (I).
2. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1, wobei R1 für Fluor, Chlor, Brom, lod oder Trifluormethyl, wobei mindestens ein Substituent R1 für Fluor, Chlor, Brom oder lod steht, R2 für Fluor oder Wasserstoff n für 2, 3 oder 4, 2. Compounds of general formula (I) according to claim 1, wherein R 1 is fluorine, chlorine, bromine, iodine or trifluoromethyl, wherein at least one substituent R 1 is fluorine, chlorine, bromine or iodine, R 2 is fluorine or hydrogen n for 2, 3 or 4,
R3 für Wasserstoff, R 3 is hydrogen,
R4 für Wasserstoff, Methyl, Ethyl oder Prop-2-in-l -yl, G für CH oder N, R 4 is hydrogen, methyl, ethyl or prop-2-yn-1-yl, G is CH or N,
R6 für Chlor, Brom, Methyl oder Trifluormethyl, sowie Salze und N-Oxide von Verbindungen der Formel (I). R 6 is chlorine, bromine, methyl or trifluoromethyl, and salts and N-oxides of compounds of the formula (I).
3. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 oder 2, wobei R1 für Fluor, Chlor, Brom oder Trifluormethl steht, wobei mindestens ein Substituent R1 für Fluor oder Chlor steht, und n für 2,3 oder 4 steht sowie Salze und N-Oxide von Verbindungen der Formel (I). 3. Compounds of general formula (I) according to claim 1 or 2, wherein R 1 is fluorine, chlorine, bromine or trifluoromethyl, wherein at least one substituent R 1 is fluorine or chlorine, and n is 2,3 or 4, and Salts and N-oxides of compounds of the formula (I).
4. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1, 2 oder 3, wobei R6 für Chlor oder Methyl steht, sowie Salze und N-Oxide von Verbindungen der Formel (I). 4. Compounds of general formula (I) according to claim 1, 2 or 3, wherein R 6 is chlorine or methyl, and salts and N-oxides of compounds of formula (I).
5. Agrochemische Formulierung enthaltend Verbindungen der allgemeinen Formel (I) und / oder deren Salze gemäß einem der Ansprüche 1 bis 4 in biologisch wirksamen Gehalten von zwischen 0,00000001 und 98 Gew.-%, bezogen auf das Gewicht der agrochemischen Formulierung, sowie Streckmittel und/oder oberflächenaktive Stoffe. 5. An agrochemical formulation containing compounds of general formula (I) and / or salts thereof according to any one of claims 1 to 4 in biologically active contents of between 0.00000001 and 98 wt .-%, based on the weight of the agrochemical formulation, and extenders and / or surfactants.
6. Agrochemische Formulierung gemäß Anspruch 5 zusätzlich enthaltend einen weiteren agrochemischen Wirkstoff. 6. Agrochemical formulation according to claim 5 additionally containing a further agrochemical active ingredient.
7. Verfahren zur Bekämpfung von tierischen Schädlingen, bei dem man Verbindungen der allgemeinen Formel (I) und / oder deren Salze gemäß einem der Ansprüche 1 bis 4 auf tierische Schädlinge und/oder ihren Lebensraum einwirken lässt, wobei Verfahren zur Behandlung des menschlichen oder tierischen Körpers ausgeschlossen sind. 7. A method for controlling animal pests, which comprises allowing compounds of general formula (I) and / or salts thereof according to one of claims 1 to 4 to act on animal pests and / or their habitat, wherein methods for the treatment of human or animal Body are excluded.
8. Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4 zum Schutz des Vermehrungsmaterials von Pflanzen. 8. Use of compounds of the general formula (I) according to one of claims 1 to 4 for the protection of the propagation material of plants.
EP15704310.0A 2014-02-17 2015-02-13 Indole carboxamides and benzimidazole carboxamides as insecticides and acaricides Withdrawn EP3107896A1 (en)

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