WO2019228788A1 - Pyrorroline-2-ones à substitution 2-bromo-6-alcoxyphényle et leur utilisation comme herbicides - Google Patents

Pyrorroline-2-ones à substitution 2-bromo-6-alcoxyphényle et leur utilisation comme herbicides Download PDF

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WO2019228788A1
WO2019228788A1 PCT/EP2019/062172 EP2019062172W WO2019228788A1 WO 2019228788 A1 WO2019228788 A1 WO 2019228788A1 EP 2019062172 W EP2019062172 W EP 2019062172W WO 2019228788 A1 WO2019228788 A1 WO 2019228788A1
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plants
alkyl
methyl
compounds
ethyl
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PCT/EP2019/062172
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German (de)
English (en)
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Guido Bojack
Alfred Angermann
Andreas REMBIAK
Estella Buscato Arsequell
Stefan Lehr
Elmar Gatzweiler
Anu Bheemaiah MACHETTIRA
Christopher Hugh Rosinger
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Bayer Aktiengesellschaft
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Publication of WO2019228788A1 publication Critical patent/WO2019228788A1/fr

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    • 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
    • C07D209/54—Spiro-condensed
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof

Definitions

  • the present invention relates to novel herbicidally active 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones according to the general formula (I) or agrochemically acceptable salts thereof, as well as their use for controlling weeds and weeds in crops.
  • bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives EP-A-355 599, EP-A-415 211 and JP-A-12-053 670
  • Arylpyrrolidine-2,4-dione derivatives EP-A-377 893 and EP-A-442 077) having herbicidal, insecticidal or fungicidal activity.
  • Alkynyl-substituted-3-phenylpyrrolidine-2,4-diones with herbicidal activity are also known from WO 96/82395, WO 98/05638, WO 01/74770, WO 15/032702 or WO 15/040114.
  • the object of the present invention is consequently to provide novel compounds which do not have the disadvantages mentioned.
  • the present invention therefore relates to novel 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones of the general formula (I),
  • R 1 is (C 1 -C 6 ) alkyl, (C 2 -C 4 ) haloalkyl or (C 3 -C 6 ) cycloalkyl;
  • R 2 is (C 1 -C 2 ) -alkoxy or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl;
  • G is hydrogen, a leaving group L or a cation E, where
  • R 4 is (C 1 -C 4 ) alkyl or (C 1 -C 3 ) alkoxy (C 2 -C 4 ) alkyl;
  • R 5 is (C 1 -C 4 ) -alkyl
  • R 6 is (C 1 -C 4 ) -alkyl, an unsubstituted phenyl or a mono- or polysubstituted with halogen,
  • R 7 , R 7 'independently of one another are methoxy or ethoxy
  • R 8 , R 9 each independently represent methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6-, or 7-membered heterocycle with an oxygen or Form sulfur atom,
  • E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
  • an ammonium ion in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups (Ci-Cio) - alkyl or (C3-C7) -cycloalkyl can be replaced, whereby these independently of each other in each case one or more times with fluorine, chlorine, bromine, cyano, hydroxy substituted or interrupted by one or more oxygen or sulfur atoms could be,
  • a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion for example, in each case morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated l, 4-diazabicyclo [1.1.2] octane (DABCO) or 1,5-diazabicyclo [4.3.0] undec -7-en (DBU),
  • DABCO 4-diazabicyclo [1.1.2] octane
  • DBU 1,5-diazabicyclo [4.3.0] undec -7-en
  • pyridine protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline , 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate or
  • Trimethylsulfoniumion may also stand for a Trimethylsulfoniumion.
  • Alkyl denotes saturated, straight-chain or branched hydrocarbon radicals with the number of carbon atoms given in each case, for example (C 1 -C 6 ) -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2 Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1
  • Alkyl substituted by halogen means straight-chain or branched alkyl groups, in which groups some or all of the hydrogen atoms may be replaced by halogen atoms, e.g. C 1 -C 2 -haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroeth
  • Alkenyl denotes unsaturated, straight-chain or branched hydrocarbon radicals having in each case the number of carbon atoms and a double bond in any desired position, for example C 2 -C 6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2 Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2- Methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-di
  • Alkynyl means straight-chain or branched hydrocarbon radicals having in each case the number of carbon atoms and a triple bond in any desired position, e.g. C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl
  • Cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents wherein substituents having a double bond on the cycloalkyl, z.
  • alkylidene group such as methylidene, are included.
  • Alkoxy represents saturated, straight-chain or branched alkoxy radicals with the number of carbon atoms given in each case, for example C 1 -C 6 -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- Dimethyl ethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3
  • Methylpentoxy 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy,
  • Alkoxy substituted by halogen means straight-chain or branched alkoxy radicals having in each case the number of carbon atoms indicated, in which groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, e.g.
  • C 1 -C 2 -haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy,
  • the compounds of the formula (I) may, depending on the nature of the substituents, be present as geo metric and / or optical isomers or mixtures of isomers, in different composition, for example, also in cis or trans form, which are defined as follows:
  • R 1 is (C 1 -C 3 ) alkyl, (C 2 -C 3 ) haloalkyl or cyclopropyl;
  • R 2 is (C 1 -C 2 ) -alkoxy or (C 1 -C 2 ) -alkoxy- (C 1 -C 2 ) -alkyl;
  • G is hydrogen, a leaving group L or a cation E, where
  • R 4 is C 1 -C 12 alkyl or (C 1 -C 2 ) alkoxyethyl
  • R 5 is (Ci-Cü-alkyl
  • R 6 denotes (C 1 -C 4) -alkyl, an unsubstituted phenyl or a phenyl which is monosubstituted or polysubstituted by halogen, methyl, methoxy, halomethoxy, nitro or cyano,
  • E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
  • R 1 is methyl or ethyl
  • R 2 is methoxy, ethoxy or methoxymethyl
  • G is hydrogen, a leaving group F or a cation E, where
  • R 4 is methyl, ethyl, n-propyl, isopropyl or t-butyl;
  • R 5 is methyl or ethyl
  • E is a sodium or potassium ion, an ion equivalent of magnesium, calcium or aluminum.
  • R 1 and R 2 have the abovementioned meaning
  • R 10 is alkyl, preferably methyl or ethyl, optionally in the presence of a suitable solvent or diluent, cyclized with a suitable base with formal cleavage of the group R 10 OH, or b) a compound of the general formula (Ia),
  • R 1 and R 2 have the meanings given above, for example with a compound of general formula (III), Hal-L (III) in which L has the abovementioned meaning and Hal is a halogen, preferably chlorine or bromine , optionally in the presence of a suitable solvent or diluent, and a suitable base, reacting,
  • Suitable leaving groups W are, for example, halogen atoms such as chlorine, bromine or iodine, alkylsulfone ester groups such as triflate, mesylate or nonaflate, magnesium chloride, magnesium bromide, zinc chloride, a trialkyltin radical, carboxyl and boric acid radicals such as -B (OHh or -B (Oalkyl) 2 Pd.sup. +
  • Complexes are particularly well suited as catalysts, and in many cases the addition of Cu (I) salts can also be very advantageous, and also figured materials such as 1,4-bis (diphenylphosphino) butane can be used.
  • the required precursors of the general formula (XII) can be obtained, for example, by using a compound having the general formula (XIV), in which R 1 , R 11 and U have the abovementioned meaning, according to the already described cross-coupling methodology with a Compound of the general formula (V), in which W has the meaning indicated above, and the resulting carboxylic acid esters are cleaved by standard methods:
  • precursors of general formula (XVI) can be obtained by standard commercial methods such as bromination and / or alkylation from commercially available aminonitrophenols.
  • the present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied.
  • the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschinene.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage stage, but then stop their growth.
  • the compounds according to the invention can have selectivities in useful cultures and can also be used as nonselective herbicides.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain active ingredients used in the agricultural industry, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Other particular properties are tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation.
  • the compounds of the formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044, EP 0131624).
  • genetic modifications of crop plants have been described for the purpose of modifying the starch synthesized in the plants (eg WO 92/011376 A, WO 92/014827 A, WO 91/019806 A), transgenic crop plants which are resistant to certain glufosinate-type herbicides (US Pat.
  • Transgenic crops such as cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A).
  • Transgenic crops with modified fatty acid composition WO 91/013972 A.
  • genetically modified crops with new content or secondary substances for example, new phytoalexins which cause increased disease resistance (EP 0309862 A, EP 0464461 A)
  • transgenic crop plants produce pharmaceutically or diagnostically important proteins ("molecular pharming") transgenic crops that are characterized by higher yields or better quality transgenic crop plants which are characterized by a combination of the above-mentioned new properties (“gene stacking")
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
  • base exchanges can be made, partial sequences removed or natural or synthetic sequences added.
  • adapters or linkers can be attached to the fragments, see eg Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell.
  • the coding region is linked to DNA sequences which ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. 2,4-D, dicamba or against herbicides containing essential plant enzymes, e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat Dioxygenases (HPPD) inhibit or resistant to herbicides from the group of sulfonylureas, the glyphosate, glufosinate or Benzoylisoxazole and analogues, or against any combination of these agents resistant.
  • growth factors such as e.g. 2,4-D, dicamba or against herbicides containing essential plant enzymes, e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat Dioxygenases (HPPD) inhibit or resistant to herbicides from the group of sul
  • the compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones.
  • the Inventive compounds in transgenic crops such.
  • corn or soybean with the trade name or the name OptimumTM GATTM Glyphosate ALS Tolerant can be used.
  • the invention therefore also relates to the use of the compounds of the formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase are based, can be used, for example from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc.
  • herbicidal mixture partners examples include:
  • plant growth regulators as possible mixing partners are:
  • Safeners which can be used in combination with the compounds of the formula (I) according to the invention and, if appropriate, in combinations with further active ingredients such as, for example, insecticides, acaricides, herbicides, fungicides as listed above, are preferably selected from the group consisting of: S 1) compounds of the formula (S 1),
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical selected from the group consisting of the monounsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom are present in the ring, preferably one Remainder of the group (WA 1 ) to (WA 4 ),
  • ni A is 0 or 1;
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is bonded via the N- Atom is connected to the Carbony l distr in (Sl) and is unsubstituted or substituted by radicals from the group (C1-C4) alkyl, (Ci-C4) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHRA 4 or N (CI F) 2, in particular the formula ORA 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • R A 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or COORA 9 , where RA 9 hydrogen, (Ci-Cs ) Alkyl, (C 1 -C 5) -haloalkyl, (C 1 -C 4) -alkoxy- (C 1 -C 4) -alkyl, (C 1 -C 6 ) hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri (C 1 -C 4) -alkyl-silyl;
  • RA 6 , RA 7 , RA 8 are identical or different hydrogen, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 3 -C 12) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (Sl a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1 Ethyl (2- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S 1-1) ("mefenpyr-diethyl”), and related compounds as described in the A-91/07874 are described; b) Derivatives of dichlorophenylpyrazolecarbox
  • R B 1 is halogen, ( C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, nitro or (C 1 -C 4) haloalkyl; ne is a natural number of 0 to 5, preferably 0 to 3;
  • R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is connected via the N atom with the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR B 3 , NHR B 4 or NfCl Fb, in particular of the formula OR B 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (Ci-Ce) alkyl, (Ci-Ce) alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4) alkyl radicals or by [(C 1 -C 3) alkoxy] carbonyl; preferably: a) Compounds of the 8-quinolinoxyacetic acid (S2 a), preferably (5-chloro-8-quinolinoxy) acetic acid, ethyl (l-methylhexyl) ester ( "cloquintocet-mexyl”) (S2-1), (5- Chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinolinoxy) acetic acid 4-allyloxy-butyl ester (S2-3),
  • Rc 1 is (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C3-C7) cycloalkyl, preferably dichloromethyl;
  • Rc 2 , Rc 3 are identical or different hydrogen, (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C i -C) haloalkyl, (C 2 -C ) haloalkenyl, (Ci-C) alkylcarbamoyl (Ci-C) alkyl, (C 2 - C 4) Alkenylcarbamoyl- (C i -C 4 alkyl), (C i -C 4) alkoxy (C i -C 4 ) alkyl, dioxolanyl (C 1 -C 4 ) alkyl,
  • Thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably:
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8), "diclonone” (dicyclonone) or "BAS145138” or “LAB145138” (S3-9)
  • a D is S0 2 -NR D 3 -C0 or C0-NR D 3 -S0 2 X D is CH or N;
  • RD 1 is CO-NR D 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy, nitro, (C 1 -C 4) -alkyl, (C 1 -C 4) -alkoxy, (C 1 -C 4) -alkylsulfonyl, (C 1 -C 4) -alkoxycarbonyl or ( Ci-C4) alkylcarbonyl;
  • RD 3 is hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl or (C 2 -C 4) alkynyl; RD 4 is halogen, nitro, (C 1 -C 4) -alkyl, (C 1 -C 4) -haloalkyl, (C 1 -C 4) -haloalkoxy, (C 3 -C 6) -cycloalkyl,
  • Phenyl (Ci-C 4) alkoxy, cyano, (Ci-C 4) alkylthio, (Ci-C4) alkylsulfinyl, (Ci-C 4) alkylsulfonyl, (Ci- C4) alkoxycarbonyl or (Ci-C4) alkylcarbonyl;
  • RD 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl, phenyl or 3- to 6-membered heterocyclyl containing VD heteroatoms from the group consisting of nitrogen, oxygen and sulfur, where the seven latter radicals are represented by VD substituents from the group halogen, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkoxy, ( Ci-C 2 ) alkylsulfinyl, (Ci-C 2 ) alkylsulfonyl, (C 3 -C 6) cycloalkyl, (Ci-C4) alkoxycarbonyl, (Ci-C4) alkylcarbonyl and phenyl and in the case of cyclic radicals also
  • RD 6 is hydrogen, (C I -C ⁇ ) alkyl, (C2 -Ce) alkenyl or (C 2 -C 6) -alkynyl, where the three last-mentioned radicals are substituted by VD radicals from the group halogen, hydroxy, (C1-C4 ) Alkyl, (C 1 -C 4) alkoxy and (C 1 -C 4) alkylthio, or
  • RD 7 is hydrogen, (Ci-C4) alkylamino, di- (Ci-C4) alkylamino, (Ci-Ce) alkyl, (C3-C6) cycloalkyl, where the 2 latter radicals by VD substituents selected from the group halogen, (Ci -C4) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals are also (C1-C4) alkyl and (Ci-C4) haloalkyl substituted; nD is 0, 1 or 2; ni D is 1 or 2;
  • VD is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which are, for example, B. are known from WO-A-97/45016
  • RD 7 (Ci-Ce) alkyl, (C3-C6) cycloalkyl, where the 2 latter radicals by VD substituents selected from the group consisting of halogen, (Ci-C4) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci-C4) alkylthio and in the case of cyclic radicals also (C1-C4) alkyl and (Ci-C4) haloalkyl are substituted; RD 4 is halogen, (C i -CU) alkyl, (C i -C 4 ) alkoxy, CF 3; m D 1 or 2;
  • VD is 0, 1, 2 or 3; such as
  • RD R 8 and D 9 are independently hydrogen, (Ci-C 8) alkyl, (C3-C8) cycloalkyl, (c3-0 C 6) alkenyl, (C 3 -C 6) alkynyl, RD 4 halogen, (C i -CU) alkyl, (C i -C 4 ) alkoxy, CF 3
  • IU D is 1 or 2; for example, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • N-phenylsulfonylterephthalamides of the formula (S4 d ) which are known, for example, from CN 101838227,
  • RD 4 is halogen, (C i -CU) alkyl, (C i -C 4 ) alkoxy, CF 3; ni D 1 or 2;
  • RD 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl.
  • Carboxylic acid derivatives (S5) e.g.
  • Dihydroxybenzoic acid 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • RE 1 , RE 2 are, independently of one another, halogen, (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkylamino, di (C 1 -C 4) alkylamino, nitro;
  • a E is COORE 3 or COSRE 4
  • RE 3 , RE 4 are, independently of one another, hydrogen, (C 1 -C 4 ) -alkyl, (C 2 -C 6 ) -alkenyl,
  • P E 2 , n E 3 are independently 0, 1 or 2, preferably:
  • Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1).
  • RF 2 is hydrogen or (C 1 -C 4 ) alkyl
  • RF 3 is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three, same or different radicals from the group consisting of halogen and alkoxy substituted; or their salts, preferably compounds wherein
  • n F is an integer from 0 to 2
  • RF 2 is hydrogen or (Ci-C4) alkyl
  • RF 3 is hydrogen, (C 1 -C 6) alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three, identical or different Radicals from the group consisting of halogen and alkoxy substituted, mean, or their salts.
  • R G 1 is halogen, (C 1 -C 4) alkyl, methoxy, nitro, cyano, CF 3, OCF 3
  • Y G , Z G independently of one another O or S, II G is an integer from 0 to 4,
  • R G 2 (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl,
  • R G 3 is hydrogen or (Ci-Ce) alkyl.
  • Si l oxyimino compound type compounds
  • seed dressing agents such as e.g. "Oxabetrinil” ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S 11-1), which is known as a seed safener for millet against damage by metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) oxime) (Si l -2), which was used as seed dressing -Safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.
  • Isothiochromanone (S12) class agents e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds of WO-A- 1998/13361.
  • naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S 13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • RH 1 is a (Ci-C 6 ) haloalkyl radical and RH 2 is hydrogen or halogen and
  • RH 3 , RH 4 are independently hydrogen, (Ci-Ci 6 ) alkyl, (C 2 -C 16) alkenyl or (C 2 -C 6 ) alkynyl, each of the last-mentioned 3 unsubstituted or by one or more radicals from the group halogen , Hydroxy, cyano, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, (Ci-C4) alkylthio, (Ci-C4) alkylamino, di [(Ci-C4) alkyl] -amino, [(Ci-C4 ) Alkoxy] carbonyl, [(C 1 -C 4) haloalkoxy] carbonyl, (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or (
  • RH 3 (C 1 -C 4) alkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 4) haloalkoxy and
  • R H 4 is hydrogen or (C 1 -C 4 ) -alkyl or
  • RH 3 and RH 4 together with the directly attached N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, may also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group consisting of N, O and S, and which may be unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy and (C 1 -C 4 ) 4 ) alkylthio is substituted, means.
  • Particularly preferred safeners are mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dichloromide and metcamifen.
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type (wetting agents, dispersants) in addition to the active ingredient except a diluent or inert substance.
  • the herbicidal active compounds are finely ground, for example, in customary apparatuses such as hammer mills, blower mills and jet mills, and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic Solvents such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers) produced.
  • organic Solvents such as butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers) produced.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products
  • alkyl polyethers sorbitan esters such as sorbitan fatty acid esters or polyoxethylenesorbitan esters such as polyoxyethylene sorbitan fatty acid esters ,
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They may, for example, be prepared by wet-milling by means of commercial beads and optionally adding surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • Emulsions e.g. Oil-in-water (EW) emulsions may be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as those described e.g. listed above for the other formulation types.
  • EW Oil-in-water
  • Granules can either be prepared by atomizing the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the active ingredient concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dust-like formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient
  • sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, ground or scattered granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of formula (I) and their salts varies. It can vary within wide limits, for example between 0.001 and 10.0 kg / ha or more of active substance, but is preferably between 0.005 to 5 kg / ha, more preferably in the range of 0.01 to 1.5 kg / ha, in particular preferably in the range of 0.05 to 1 kg / ha g / ha. This applies to pre-emergence or post-emergence applications.
  • Carrier means a natural or synthetic, organic or inorganic substance, with which the active ingredients for better applicability, v.a. for application to plants or plant parts or seeds, mixed or combined.
  • the carrier which may be solid or liquid, is generally inert and should be useful in agriculture.
  • Suitable solid or liquid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol , organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
  • Suitable solid 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 flour and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Suitable liquefied gaseous diluents or carriers are those liquids 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.
  • Aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • 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.
  • 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.
  • the inventive compositions may additionally contain other ingredients, such as surfactants.
  • surface-active substances are emulsifying and / or foam producing agents, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surfactants.
  • examples thereof 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, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric 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, alkylsul
  • the presence of a surfactant is necessary when one of the active ingredients and / or one of the inert carriers is not soluble in water and when applied in water.
  • the proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.
  • Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90%. Active ingredient, most preferably between 10 and 70 weight percent.
  • the active compounds or compositions according to the invention as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, Kapselsus pensionen, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for Seed treatment, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macro granules, microgranules, oil dispersible powders, oil miscible flowable concentrates, oil miscible liquids, foams, pastes , Pesticide-coated seeds, suspension concentrates, suspension-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, active substance impre
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one customary diluent, diluent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, defoaming agents, preservatives , secondary thickeners, adhesives, gibberellins and other processing aids.
  • compositions according to the invention comprise not only formulations which are already ready for use and which can be applied to the plant or the seed with a suitable apparatus, but also commercial concentrates which have to be diluted with water before use.
  • active compounds according to the invention as such or in their (commercial) formulations and in the formulations prepared from these formulations in admixture with other (known) active ingredients such as insecticides, Fockstoffen, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, Fertilizers, safeners or semiochemicals.
  • active ingredients such as insecticides, Fockstoffen, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, Fertilizers, safeners or semiochemicals.
  • the treatment according to the invention of the plants and plant parts with the active compounds or agents is carried out directly or by acting on their environment, Febensraum or Fagerraum according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, sprinkling, foaming, brushing, spreading, pouring, drip irrigation and in the case of propagation material, in particular for seeds, Furthermore, by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer wrapping, etc. It is also possible to apply the active ingredients by the Ultra-Fow-Volume method or to inject the active compound preparation or the active ingredient itself into the soil.
  • transgenic seed As also described below, the treatment of transgenic seed with the inventive active ingredients or agents is of particular importance.
  • the heterologous gene in transgenic seed can be derived, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • this heterologous gene is derived from Bacillus sp., Wherein the gene product has an activity against the European corn borer (European corn borer) and / or Western Com Rootworm.
  • the heterologous gene is from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a state that is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvest 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 which has been harvested, cleaned and dried to a moisture content below 15% by weight.
  • seed may also be used which, after drying, e.g. treated with water and then dried again.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compounds according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as UFV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, Konser undungsstoff, secondary thickeners, adhesives, gibberellins and water ,
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, Konser undungsstoff, secondary thickeners, adhesives, gibberellins and 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. As Examples include the known under the names rhodamine B, CI Pigment Red 112 and CI Solvent Red 1 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.
  • Preferably usable are 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 tristryrylphenol 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.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • all substances which can be used for such purposes in agrochemical compositions can be present in the case-mimetic formulations which can be used according to the invention.
  • examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners 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. 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 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, including seed of transgenic plants. It can work in conjunction with the Expression-formed substances also experience additional synergistic effects.
  • the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
  • all mixing devices customarily usable for the dressing can be considered.
  • the seed is introduced into a mixer which adds the desired amount of seed dressing formulations, either as such or after prior dilution with water, and mixes until uniformly distributing the formulation on the seed ,
  • a drying process follows.
  • the active compounds according to the invention are suitable for good plant tolerance, favorable toxicity to warm-blooded animals and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the harvested crop. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • plants which can be treated according to the invention the following main crops are mentioned: maize, soybean, cotton, Brassica oilseeds such as Brassica napus (eg canola), Brassica rapa, B. juncea (eg (field) mustard) and Brassica carinata, rice, Wheat sugar beet, cane, oats, rye, barley, millet, triticale, flax, wine and various fruits and vegetables of various botanical taxa such as Rosaceae sp.
  • pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example, banana trees and plantations), Rubiaceae sp.
  • Theaceae sp. for example, coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example, lemons, organs and grapefruit
  • Solanaceae sp. for example, tomatoes, potatoes, peppers, eggplants
  • Liliaceae sp. Compositae sp.
  • lettuce, artichoke and chicory - including root chicory, endive or common chicory for example, Umbelliferae sp.
  • Umbelliferae sp. for example, carrots, parsley, celery and celeriac
  • Cucurbitaceae sp. for example cucumber - including gherkin, squash, watermelon, gourd and melons
  • Cruciferae sp. for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage
  • Leguminosae sp. for example, peanuts, peas, and beans - such as barley bean and field bean
  • Chenopodiaceae sp. for example, Swiss chard, fodder beet, spinach, beetroot), Malvaceae (for example okra), asparagaceae (for example asparagus); Crops and Ornamental plants in the garden and forest; and each genetically modified species of these plants.
  • plants and their parts can be treated.
  • wild-occurring or by conventional biological breeding methods such as crossing or protoplast fusion obtained plant species and Pflan censorten and their parts 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 “plant parts” has been explained above. It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the erfmdungshacke treatment method can for the treatment of genetically modified organisms (GMOs), z.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • the term "heterologous gene” essentially refers to a gene that is provided or assembled outside the plant and that when introduced into the nuclear genome, chloroplast genome or mitochondrial genome imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide, or that it downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA Interference]).
  • a heterologous gene present in the genome is also referred to as a transgene.
  • a transgene, which is defined by its specific Vorhegen in the plant genome, is referred to as a transformation or transgenic event.
  • the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
  • the following effects are possible, which go beyond the actually expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active compounds and compositions which can be used according to the invention, better Plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or water or soil salinity, increased flowering, emolliency, ripening, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the enceary products, higher sugar concentration in the fruits, better shelf life and / or processability of the harvested products.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
  • nematode-resistant plants are e.g. following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417,
  • Plants which can be treated according to the invention are hybrid plants which already express the properties of the heterosis or of the hybrid effect, which generally leads to higher yields, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
  • the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H. Plants tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant to glyphosate by various methods. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above mentioned genes. Plants expressing EPSPS genes conferring glyphosate tolerance are described. Plants which confer other genes which confer glyphosate tolerance, e.g. Decarboxylase genes are described.
  • herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by having an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein of Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenase
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene coding for an HPPD-tolerant enzyme, with a gene coding for a prephenate dehydrogenase enzyme, as in WO 2004/024928 is described.
  • plants can be made even more tolerant to HPPD inhibitors by incorporating into their genome a gene encoding an enzyme that metabolizes or degrades HPPD inhibitors, such as e.g. CYP450 enzymes (see WO 2007/103567 and WO 2008/150473).
  • ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants that are tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (see, for example, for soybean US 5,084,082, for rice WO 97/41218, for sugar beet US 5,773,702 and WO 99/057965, for salad US 5,198,599 or for sunflower WO 01/065922).
  • Plants or plant varieties are tolerant to abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance.
  • Particularly useful plants with stress tolerance include the following: a. Plants containing a transgene capable of reducing the expression and / or activity of the poly (ADP-ribose) polymerase (PARP) gene in the plant cells or plants. b. Plants containing a stress tolerance enhancing transgene capable of reducing the expression and / or activity of the PARC-encoding genes of the plants or plant cells; c.
  • Plants which contain a stress-promoting transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.
  • Plants or plant cultivars obtained by plant biotechnology methods such as genetic engineering which can also be treated according to the invention have an altered quantity, quality and / or storability of the enceary product and / or altered properties of certain components of the enceary product; such as:
  • Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification.
  • Examples are plants, the Polyfmctose, in particular of the Inulin and levan types, plants that produce alpha-l, 4-glucans, plants that produce alpha-l, 6-branched alpha-l, 4-glucans, and plants that produce alternan.
  • Transgenic plants or hybrid plants such as onions with certain properties such as "high soluble solids content", low pungency (LP) and / or long storage (LS) ).
  • Plants or plant varieties are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants such as cotton plants containing an altered form of cellulose synthase genes; b) plants such as cotton plants containing an altered form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants having increased expression of sucrose phosphate synthase; c) plants such as cotton plants with increased expression of sucrose synthase; d) plants such as cotton plants in which the timing of the passage control of the Plasmodesmen is changed at the base of the fiber cell, z.
  • Plants or plant varieties which can also be treated according to the invention are plants such as oilseed rape or related Brassica plants with altered oil composition properties.
  • Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include: a) plants, such as oilseed rape plants, which produce oil of high oleic acid content; b) plants such as oilseed rape plants, which produce oil with a low linolenic acid content. c) plants such as rape plants that produce oil with a low saturated fatty acid content.
  • Plants or plant varieties which can be obtained by plant biotechnology methods such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (eg RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
  • viruses which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as potato late blight (eg RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
  • viruses which are virus-resistant, e.g. against
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered seed shattering properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered properties, and include plants such as oilseed rape with delayed or reduced seed failure.
  • transgenic plants which can be treated according to the present invention are plants having transformational events or combinations of transformation events which are the subject of issued or pending petitions in the United States Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for the non-regulated status.
  • APIS United States Animal and Plant Health Inspection Service
  • USA United States Department of Agriculture
  • the information is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the website http://www.aphis.usda.gov/brs/not_reg.html.
  • APHIS had either given or is pending petitions with the following information:
  • Transgenic phenotype the trait conferred on the plant by the transformation event.
  • APHIS Documente various documents that may be published by APHIS regarding the petition or may be obtained from APHIS upon request.
  • transgenic plants which can be treated according to the invention are plants with one or more genes coding for one or more toxins, the transgenic plants offered under the following commercial names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, Soybeans
  • KnockOut® for example corn
  • BiteGard® for example maize
  • BT-Xtra® for example corn
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example corn
  • Protecta® and NewLeaf® pot
  • Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example corn.
  • Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
  • a dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or salts thereof and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as a wetting and dispersing agent and grinding in a pin mill.
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO ) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) and milled in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granules are obtained by
  • a water-dispersible granules are also obtained by
  • Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then converted as aqueous suspension or emulsion with a water application rate of 600 to 800 1 / ha with the addition of 0.2% wetting agent applied to the surface of the cover soil.
  • ALOMY Alopecurus myosuroides
  • SETVI Setaria viridis
  • AMARE Amaranthus retroflexus AVEFA: Avena fatua
  • ECHCG Echinochloa crus-galli
  • VERPE Veronica persica VIOTR: Viola tricolor
  • POLCO Polygonum convolvulus ABUTH: Abutylon threophrasti
  • HORMU Hordeum murinum
  • the compounds Nos. 1.01, 1.02, 1.03, 1.04, 1.08 and 1.09 in Table 3 at a rate of 320 g / ha each have a 100% action against Avena fatua, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis and Hordeum murinum.
  • Table 4 Pre-emergence effect at 80 g / ha
  • the compounds Nos. 1.01, 1.02, 1.03, 1.04, 1.08, 1.09, 1.14, 1.15 and 1.16 at a rate of 80 g / ha each have a 90-100% action against Alopecurus myosuroides, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis and Hordeum murinum.
  • the compounds according to the invention are therefore suitable in the pre-emergence process for
  • Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the
  • compounds Nos. 1.01, 1.03, 1.04, 1.08 and 1.09 in Table 5 at a rate of 80 g / ha each have a 90-100% action against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum , Setaria viridis and Hordeum murinum.
  • the compounds according to the invention are therefore suitable for postemergence treatment of unwanted plants.

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Abstract

L'invention concerne de nouvelles pyrroline-2-ones à substitution 2-bromo-6-alcoxyphényle, à action herbicide, de formule générale (I) ou des sels agrochimiquement acceptables de celles-ci, ainsi que leur utilisation pour lutter contre les plantes adventices et les mauvaises herbes dans des cultures de plantes utiles.
PCT/EP2019/062172 2018-05-29 2019-05-13 Pyrorroline-2-ones à substitution 2-bromo-6-alcoxyphényle et leur utilisation comme herbicides WO2019228788A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3793977A1 (fr) * 2018-05-15 2021-03-24 Bayer Aktiengesellschaft Pyrrolin-2-ones à substitution 2-bromo-6-alcoxyphényle et leur utilisation comme herbicides
WO2021239673A1 (fr) 2020-05-27 2021-12-02 Bayer Aktiengesellschaft Pyrroline-2-ones substituées et leur utilisation en tant qu'herbicides

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