WO2021028419A1 - 3-(2-hétéroaryloxyphényle)isoxazolines substituées, leurs sels et leur utilisation en tant que substances actives herbicides - Google Patents

3-(2-hétéroaryloxyphényle)isoxazolines substituées, leurs sels et leur utilisation en tant que substances actives herbicides Download PDF

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WO2021028419A1
WO2021028419A1 PCT/EP2020/072462 EP2020072462W WO2021028419A1 WO 2021028419 A1 WO2021028419 A1 WO 2021028419A1 EP 2020072462 W EP2020072462 W EP 2020072462W WO 2021028419 A1 WO2021028419 A1 WO 2021028419A1
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alkyl
plants
compounds
general formula
cyano
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PCT/EP2020/072462
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English (en)
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Michael Charles MCLEOD
David Michael BARBER
Harald Jakobi
Ralf Braun
Dirk Schmutzler
Elisabeth ASMUS
Anu Bheemaiah MACHETTIRA
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Bayer Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • Substituted 3- (2-heteroaryloxyphenyl) isoxazolines and their salts and their use as herbicidal active ingredients Description
  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grasses in crops of useful plants.
  • this invention relates to substituted 3- (2-heteroaryloxyphenyl) isoxazolines and their salts, processes for their preparation and their use as herbicides.
  • Plant protection agents known to date for the selective control of harmful plants in crops of useful plants or active ingredients for controlling undesired vegetation sometimes have disadvantages when they are used, be it that they (a) have no or insufficient herbicidal activity against certain harmful plants, (b) too little Spectrum of harmful plants that can be controlled with an active ingredient, (c) too low selectivity in crops of useful plants and / or (d) have a toxicologically unfavorable profile.
  • active ingredients which can be used as plant growth regulators in some useful plants lead to undesirably reduced crop yields in other useful plants or are incompatible with the cultivated plant or only compatible with a narrow application rate range.
  • the present invention thus provides selected substituted 3- (2-heteroaryloxyphenyl) isoxazolines of the general formula (I) or their salts wherein Z is -CR 7 - or -N-, R 1 and R 2 independently of one another are hydrogen, halogen, hydroxy, amino, cyano, nitro, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -Haloalkyl, (C 3 -C 6 ) -cycloalkyl (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -haloalkenyl, (C 2 -C 4 ) -alkynyl, (C 2 -C 4 ) - haloalkynyl, (C 1 -C 4) alkoxy, (C 1 -C 4) -haloalkoxy, (C 1 -C 6) cycloalkoxy, (C 1 - C 4) alk
  • the compounds of general formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, form salts. These salts then contain the conjugate base of the acid as an anion.
  • a suitable inorganic or organic acid such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic
  • Suitable substituents which are present in deprotonated form can form internal salts with groups which can themselves be protonated, such as amino groups. Salt formation can also take place through the action of a base on compounds of the general formula (I).
  • Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate.
  • salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , in which R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
  • the substituted 3- (2-heteroaryloxyphenyl) isoxazolines of the general formula (I) according to the invention can, depending on external conditions such as pH, solvent and temperature, possibly exist in various tautomeric structures, all of which are encompassed by the general formula (I) .
  • the compounds of the formula (I) according to the invention and their salts are also referred to below as “compounds of the general formula (I)”.
  • the preferred subject matter of the invention are compounds of the general formula (I) in which Z represents -CR 7 - or -N-, R 1 and R 2 independently of one another represent hydrogen, halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 3 - C 6 ) -cycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -haloalkenyl, (C 2 -C 4 ) -alkynyl or (C 2 -C 4 ) -haloalkynyl, R 3 and R 4 independently of one another represent hydrogen, halogen, cyano, formyl, formamide, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 4
  • Particularly preferred subject matter of the invention are compounds of the general formula (I) in which Z is -CR 7 - or -N-, R 1 and R 2 independently of one another are hydrogen, halogen, (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -haloalkyl, R 3 and R 4 independently of one another represent hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -alkynyl, (C 1 -C 4 ) -alkoxy, cyano, carboxyl, (C 1 -C 4 ) -alkoxycarbonyl, carboxy- (C 1 -C 4 ) alkyl, (C 1 -C 4) alkoxycarbonyl (C 1 -C 4)
  • Very particularly preferred subject of the invention are compounds of the general formula (I) in which Z stands for -CR 7 - or -N-, R 1 stands for hydrogen, R 2 stands for hydrogen, R 3 and R 4 independently of one another are hydrogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy, cyano, carboxyl, (C 1 -C 4 ) -alkoxycarbonyl, carboxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -Alkoxycarbonyl- (C 1 -C 4 ) -alkyl, cyano- (C 1 -C 4 ) -alkyl or aminocarbonyl, or R 3 and R 4 together form an alkyl ring through - (CH 2 ) m -, where m is 2, 3 or 4, R 5 is independently halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1
  • Extremely preferred subject of the invention are compounds of the general formula (I), in which Z is -CR 7 - or -N-, R 1 is hydrogen, R 2 is hydrogen, R 3 is hydrogen, methyl, trifluoromethyl, methoxy, ethoxy, Cyano, methoxycarbonyl, carboxyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonyl-1-ethyl, carboxymethyl, carboxy-1-ethyl, cyanomethyl or aminocarbonyl, R 4 represents hydrogen or methyl, or R 3 and R 4 together represent an alkyl ring through - (CH 2 ) m - form, where m is 2, 3 or 4, R 5 is independently fluorine, bromine, methyl, ethyl or cyano, n is 0 or 1, R 6 is hydrogen, fluorine or chlorine, and R 7 represents hydrogen or fluorine.
  • R 1 is hydrogen
  • R 2 is hydrogen
  • R 3 is hydrogen, methyl, triflu
  • radical definitions given above apply both to the end products of the general formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined as desired with one another, that is to say also between the specified preferred ranges.
  • compounds according to the invention of the general formula (I) mentioned or their are Salts or their use according to the invention of particular interest, in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
  • the terms used above and below are explained.
  • the general rule for the designation of chemical groups is that the connection to the framework or the rest of the molecule takes place via the last-mentioned structural element of the chemical group in question , ie for example in the case of (C 2- C 8 ) -alkenyloxy via the oxygen atom, and in the case of heterocyclyl- (C 1 -C 8 ) -alkyl or R 12 O (O) C- (C 1 -C 8 ) -Alkyl in each case via the carbon atom of the alkyl group.
  • alkylsulfonyl on its own or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 4 carbon atoms, for example (but not limited to) (C 1 -C 4 ) -alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl , 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl.
  • alkylthio on its own or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 4 carbon atoms, such as (C 1 -C 4 ) -alkylthio, for example (but not limited to) (C 1 -C 4 ) -Alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio.
  • alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl.
  • Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. B.
  • (but not limited to) (C 1 -C 4 ) -alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy.
  • Cycloalkoxy means a cycloalkyl radical bonded via an oxygen atom.
  • the number of carbon atoms relates to the alkyl radical in the alkylcarbonyl group.
  • the number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group.
  • halogen means, for example, fluorine, chlorine, bromine or iodine. If the term is used for a radical, "halogen” means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted and in the latter case is referred to as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • the prefix “bis” also includes the combination of different alkyl radicals, e.g. B. methyl (ethyl) or ethyl (methyl).
  • perhaloalkyl also includes the term perfluoroalkyl.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4 ) -alkyl means a shorthand for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to the range given for carbon atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2 -Propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals with a larger specified range of carbon atoms e.g. B.
  • (C 1 -C 6 ) -Alkyl accordingly also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
  • the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including those in composite radicals, are preferably the lower carbon skeletons, for example with 1 to 6 carbon atoms or, in the case of unsaturated groups, with 2 to 6 carbon atoms.
  • Alkyl radicals including those in the composite radicals such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present.
  • alkenyl also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as for example allenyl (1,2-propadienyl) and 1,2-butadienyl.
  • Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, e.g.
  • alkynyl particularly also includes straight-chain or branched open-chain hydrocarbon radicals with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl.
  • (C 2 -C 4 ) -alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl.
  • cycloalkyl means a carbocyclic, saturated ring system with preferably 3-6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, AMino, alkylamino, bisalkylamino, alkocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • cyclic systems with substituents are included, with substituents with a double bond on the cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included.
  • multicyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [1.1.1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1 ] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl and adamantane -2-yl, but also systems such as B.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-6 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl , 3-Cyclohexenyl, 1,3-Cyclohexadienyl or 1,4-Cyclohexadienyl, with substituents with a double bond on the cycloalkenyl radical, e.g. B. an alkylidene group such as methylidene are included.
  • alkylidene e.g. B. also in the form (C 1 -C 10 ) -Alkylidene, denotes the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • alkylidene denotes the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Remnants are e.g. B.
  • cycloalkylidene a carbocyclic radical which is bonded via a double bond.
  • Arylalkyl stands for an aryl radical attached via an alkyl group.
  • haloalkylthio - on its own or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably with 1 to 4 carbon atoms, such as (C 1 -C 4 ) -haloalkylthio, e.g.
  • trifluoromethylthio Pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • "trialkylsilyl” - on its own or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 6 carbon atoms, such as tri- [(C 1 -C 2 ) -alkyl] silyl, eg (but not limited to) trimethylsilyl, triethylsilyl.
  • the compounds can form tautomers by hydrogen shift, which structurally formally would not be covered by the general formula (I), then these tautomers are nevertheless included in the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is the subject of consideration is.
  • many can Carbonyl compounds are present both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).
  • the compounds of the general formula (I) can be present as stereoisomers, depending on the nature and linkage of the substituents.
  • stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained during the preparation by customary separation methods. The chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale to produce test samples for biological testing.
  • stereoisomers can be selectively produced by using stereoselective reactions using optically active starting materials and / or auxiliaries.
  • the invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not indicated with their specific stereoform, and to mixtures thereof. If the compounds are obtained as solids, they can also be purified by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible in the ways described below, they can be prepared by derivatizing other compounds (I).
  • Suitable isolation, purification and stereoisomer separation processes for compounds of the general formula (I) are methods which are generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatography processes, especially column chromatography and HPLC (high pressure liquid chromatography), distillation , optionally under reduced pressure, extraction and other processes, any remaining mixtures can usually be separated by chromatographic separation, for example on chiral solid phases.
  • processes such as crystallization, for example diastereomeric salts, which can be obtained from the diastereomeric mixtures with optically active acids and, if acidic groups are present, with optically active bases, are suitable.
  • the present invention also claims processes for the preparation of the compounds of the general formula (I) according to the invention.
  • the compounds of the general formula (I) according to the invention can be prepared, inter alia, starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily manufactured building blocks.
  • the groupings R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Z and n of the general formula (I) have the meanings defined above in the schemes below, provided that the definitions are not exemplary but not restrictive.
  • Compounds according to the invention can be prepared, for example, by the method indicated in scheme 1. Scheme 1.
  • the isoxazolines of the general formula (I) can be alkylated with the pyridine or pyrimidine (E-II) via an alkylation of the phenols (EI) in the presence of bases, whereby LG is a leaving group (such as a halogen or -SO 2 Me ) is to be produced.
  • the base can be a carbonate salt of an alkali metal (such as sodium, potassium, or cesium).
  • the reactions are generally carried out in an organic solvent, such as, for example, acetonitrile, dimethylformamide, or 1-methyl-2-pyrrolidone, at temperatures between 0 ° C. and the boiling point of the solvent.
  • the phenols of the general formula (EI) can be prepared by demethylating the anisoles (E-III) in the presence of acids, such as, for example, hydrobromic acid and acetic acid, or Lewis acids, such as, for example, boron tribromide.
  • the reactions are generally in one organic solvents, such as dichloromethane, at temperatures between 0 ° C and the boiling point of the solvent.
  • the anisoles of the general formula (E-III) can be prepared via a cyclization of the chloroximes (E-IV) with alkenes (EV) in the presence of bases such as sodium hydrogen carbonate, for example.
  • the reactions are generally carried out in an organic solvent, such as, for example, isopropanol, at temperatures between 0 ° C.
  • the resulting reaction mixture is cooled to room temperature, diluted with water and extracted several times with dichloromethane. The combined organic phases are then washed with 2M HCl and water, dried over magnesium sulfate, filtered and concentrated. The yield is 4.10 g (85% of theory).
  • Synthesis stage 2 3- (2-fluoro-6-methoxyphenyl) -1-oxa-2-azaspiro [4.4] non-2-en
  • a mixture of 2.00 g (9.8 mmol) 2-fluoro-N-hydroxy-6-methoxy-benzimidoyl chloride, 1.14 ml (10.8 mmol) methylenecyclopentane and 4.13 g (49.1 mmol) NaHCO3 in 50 ml isopropanol are added Stirred room temperature for 2 h. The resulting reaction mixture is filtered and concentrated.
  • Synthesis stage 3 3-fluoro-2- (1-oxa-2-azaspiro [4.4] non-2-en-3-yl) phenol 3- (2-Fluoro-6-methoxyphenyl) -1-oxa-2-azaspiro [4.4] non-2-en (1.60 g, 6.4 mmol) is dissolved in 20 ml dichloromethane and at 0 oC with boron tribromide (1M in dichloromethane, 19.3 ml, 19.3 mmol) were added. The resulting reaction mixture is stirred at room temperature for 2 hours and then quenched with water.
  • Example No. 1-52 1 H-NMR (400 MHz, CDCl36, ppm) 8.47 (s, 2H), 7.84 (dd, 1H), 7.52-7.47 (m, 1H), 7.36-7.32 (m, 1H) , 7.21 (dd, 1H), 5.45 (dd, 1H), 3.40 (s, 3H), 3.39 (dd, 1H), 3.14 (dd, 1H).
  • the peak list of an example therefore has the form: d 1 (intensity 1 ); d 2 (intensity 2 );... ..; d i (intensity ;; ............; d n (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 real ratios of the signal intensities.
  • d i intensity ;; ............; d n (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 real ratios of the signal intensities.
  • multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown chemical shift of 1 H-NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO.
  • the tetramethylsilane peak can appear in NMR peak lists, but does not have to be.
  • the lists of 1 H-NMR peaks are similar to the classic 1 H-NMR printouts and thus usually contain all peaks that are listed in a classic NMR interpretation
  • Classic 1H-NMR printouts show solvent signals, signals of stereoisomers of the target compounds, which are also the subject of the invention, and / or peaks of impurities.
  • connection signals in the delta range of solvents and / or water our lists of 1 H-NMR peaks show the usual solvent peaks, for example peaks from DMSO in DMSO-D6 and the peak from water, which are usually in Average high intensity.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of> 90%). Such stereoisomers and / or impurities can be typical of the particular manufacturing process. Your peaks can thus help to identify the reproduction of our manufacturing process using “by-product fingerprints”.
  • An expert who calculates the peaks of the target compounds with known methods can isolate the peaks of the target compounds as required, with additional intensity filters being used if necessary. This isolation would be similar to the relevant peak picking in the classical 1 H-NMR interpretation. Further details on 1 H-NMR peak lists can be found in Research Disclosure Database Number 564025.
  • the present invention furthermore relates to the use of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1 -1) to (1-68) and / or salts thereof, each as defined above, as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.
  • the present invention also relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-1) to (1-68) and / or their salts, in each case as defined above, or - an agent according to the invention, as defined below, on the (harmful) plants, (harmful) plant seeds, the soil in which or on which the (harmful) plants grow, or the area under cultivation is applied.
  • the present invention also relates to a method for controlling undesired plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferred or particularly preferred embodiment, in particular one or more compounds of the formulas (1-1) to (1-68) and / or their salts, in each case as defined above, or - an agent according to the invention, as defined below, on unwanted plants (e.g. harmful plants such as monocotyledonous or dicotyledon weeds or unwanted crop plants), the seeds of the unwanted plants (ie plant seeds, e.g.
  • unwanted plants e.g. harmful plants such as monocotyledonous or dicotyledon weeds or unwanted crop plants
  • the seeds of the unwanted plants ie plant seeds, e.g.
  • the soil in which or on which the unwanted plants grow eg the soil of cultivated land or non-cultivated land
  • the cultivated area ie area on which the unwanted plants will grow
  • the present invention also relates to a method for controlling the growth of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-1) to (1-68) and / or their salts, in each case as defined above, or - an agent according to the invention, as defined below, the plant, the seed of the plant (i.e. plant seeds, e.g. grains, seeds or vegetative reproductive organs such as tubers or parts of shoots with buds), the soil in or on which the plants grow (e.g.
  • the seed of the plant i.e. plant seeds, e.g. grains, seeds or vegetative reproductive organs such as tubers or parts of shoots with buds
  • the soil in or on which the plants grow e.g.
  • the soil of cultivated land or non-cultivated land) or the cultivation area ie area on which the plants will grow
  • the compounds according to the invention or the agents according to the invention can be applied, for example, by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and / or post-emergence methods.
  • one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamentals, the useful plants or ornamentals in a preferred embodiment are transgenic plants.
  • the compounds of the general formula (I) according to the invention and / or their salts are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants: Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Fagrostis, Festylochata , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • the compounds of the general formula (I) according to the invention are applied to the surface of the earth (pre-emergence method) before the harmful plants (weeds and / or weeds) germinate, either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage , but then stop growing and finally die off completely after three to four weeks.
  • the active ingredients of the general formula (I) are applied to the green parts of the plant by the post-emergence method, growth stops after the treatment and the harmful plants remain in the growth stage present at the time of application or die after a certain time, so that in this way one for the Weed competition harmful to crops is eliminated very early and sustainably.
  • the compounds of the general formula (I) according to the invention have excellent herbicidal activity against monocotyledon and dicotyledon weeds, crops of economically important crops, for example dicotyledon crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledon cultures of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticale, Triticale , depending on the structure of the respective compound according to the invention and the amount applied, only insignificantly or not at all For these reasons, the present compounds are very suitable for the selective control of undesired vegetation in crops such as useful agricultural crops or ornamental crops.
  • the compounds of the general formula (I) according to the invention (depending on their particular structure and the amount applied) have excellent growth-regulatory properties in crop plants. They intervene in a regulating manner in the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesired vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledon and dicotyledon crops, since it can reduce or completely prevent storage, for example.
  • the active compounds of the general formula (I) can also be used for controlling harmful plants in crops of plants modified by genetic engineering or by conventional mutagenesis.
  • the transgenic plants are generally distinguished by particularly advantageous properties, for example by resistance to certain pesticides, 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 relate to the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with an increased starch content or a changed quality of the starch or those with a different fatty acid composition of the harvested material are known.
  • transgenic crops preference is given to using the compounds of the general formula (I) according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, for example of cereals such as wheat, barley, rye, oats, millet, rice and maize or else Cultures of sugar beet, cotton, soy, canola, potato, tomato, pea and other vegetables.
  • the compounds of the general formula (I) according to the invention can preferably also be used as herbicides in crops of useful plants which are resistant or have been made resistant by genetic engineering to the phytotoxic effects of the herbicides.
  • the compounds of the general formula (I) according to the invention can also be used for controlling harmful plants in crops of known or genetically modified plants which are yet to be developed.
  • the transgenic plants are generally distinguished by particularly advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with an increased starch content or a changed quality of the starch or those with a different fatty acid composition of the harvested material are known.
  • the use of the compounds of general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize, is preferred Cultures of sugar beet, cotton, soy, canola, potato, tomato, pea and other vegetables.
  • the compounds of the general formula (I) can preferably be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.
  • new plants with modified properties can be produced using genetic engineering.
  • Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art.
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences.
  • base exchanges can be carried out, partial sequences can be removed or natural or synthetic sequences can be added.
  • adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, one sense RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme that specifically cleaves transcripts of the gene product mentioned above.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product including any flanking sequences that may be present, as well as DNA Molecules which only comprise parts of the coding sequence, these parts having to be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein can be localized in any desired compartment of the plant cell.
  • the coding region can be linked to DNA sequences which ensure the localization in a certain compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J.11 (1992), 3219-3227).
  • 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 into whole plants using known techniques. In principle, the transgenic plants can be plants of any plant species, ie both monocotyledonous and dicotyledonous plants.
  • the compounds of the general formula (I) according to the invention can preferably be used in transgenic crops which are effective against growth substances such as dicamba or against herbicides, the essential plant enzymes, e.g.
  • acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD ) inhibit or are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydoxyphenylpyruvate dioxygenases
  • the compounds of the general formula (I) according to the invention are used in transgenic crops, in addition to the effects on harmful plants that can be observed in other crops, there are often effects that are specific to the application in the respective transgenic crop, for example a modified or specially expanded weed spectrum, that can be combated, changed application rates that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crops.
  • the use of compounds of the formula (I) according to the invention for combating harmful plants or for regulating the growth of plants also includes the case in which a compound of the general formula (I) or its salt is only used after application to the plant, in the plant or in the Soil is formed from a precursor substance ("prodrug").
  • the invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or for regulating the growth of plants, characterized in that one an effective amount of one or more compounds of the general formula (I) or their salts are applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in which or on which the plants grow, or the area under cultivation.
  • the invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of the preferred or particularly preferred embodiment, in particular one or more compounds of the formulas (I-1) to (I-68) and / or their salts, in each case as defined above, and (b) one or more other substances selected from groups (i) and / or (ii): (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those, which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or further growth regulators, (ii) one or more formulation auxiliaries customary in crop protection.
  • the agent (a) contains one or more compounds of the general formula (I) and / or their salts as defined above
  • a herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) which are customary in crop protection and selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents which are miscible with water in any ratio at 25 ° C and 1013 mbar.
  • the compounds of the general formula (I) according to the invention can be used in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain compounds of the general formula (I) and / or their salts.
  • the compounds of the general formula (I) according to the invention and / or their salts can be formulated in various ways, depending on the prevailing biological and / or chemico-physical parameters.
  • Possible formulation options include, for example: wettable powders (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), dressings, granules for litter and soil application, granules (GR) in the form of micro, spray, lift - and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC oil- or water-based
  • Wettable powders are preparations that are uniformly dispersible in water which, in addition to the active ingredient, besides a diluent or inert substance, also ionic and / or nonionic surfactants (wetting agents, dispersants), e.g.
  • polyoxyethylated alkylphenols polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, sodium ligninsulfonates, alkylbenzenesulfonates , 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalene sulfonic acid sodium or oleoylmethyltaurin acid sodium.
  • the herbicidally active ingredients are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • alkylarylsulphonic acid calcium salts such as calcium dodecylbenzenesulphonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products
  • alkyl polyethers such as sorbitan oxyethylene fatty acid esters such as sorbitan fatty acid esters such as sorbitan fatty acid esters or sorbitan oxyethylene fatty acid esters, for example sorbitan oxyethylene fatty acid esters.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, addition of surfactants, such as those already listed above for the other types of formulation.
  • Emulsions for example oil-in-water emulsions (EW) can be converted, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic Solvents and optionally surfactants, such as those already listed above for the other types of formulation, for example.
  • Granules can either be produced by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material.
  • adhesives e.g. polyvinyl alcohol, sodium polyacrylate or mineral oils
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
  • Water-dispersible granules are generally produced by the customary processes such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations, preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferred 2 to 80% by weight, of active ingredients of the general formula (I) and their salts.
  • the active ingredient concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components.
  • the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used become.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned contain, if appropriate, the respective customary adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and the Viscosity influencing agents.
  • formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of the general formula (I) according to the invention or their salts can be used as such or in the form of their preparations (formulations) combined with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators e.g. as a ready-to-use formulation or as tank mixes.
  • pesticidally active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators e.g. as a ready-to-use formulation or as tank mixes.
  • the combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active ingredients to be combined.
  • Combination partners for the compounds of the general formula (I) according to the invention in mixture formulations or in the tank mix are, for example, known active ingredients which act 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, protoporphyrinogen oxidase, can be used, as they are for example in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc.
  • the safeners which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, for example in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soy, preferably cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the amount of herbicide applied and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the general formula (I) or their mixtures with other herbicides / pesticides and are provided and used as a finished formulation or tank mix with the herbicides.
  • the herbicide or herbicide-safener formulations in commercially available form are diluted, if appropriate, in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in dust form, soil granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use. External conditions such as temperature, humidity etc.
  • the application rate of the compounds of the general formula (I) and / or their salts can vary within wide limits.
  • the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence use.
  • the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha Ha. This applies to both pre-emergence and post-emergence use.
  • the application as a stalk shortener can take place in different stages of the growth of the plants.
  • mixed formulations or in a tank mix are, for example, known active ingredients which act 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, can be used, such as those from Weed Research 26 (1986) 441-445 or "The Pesticide Manual ", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited there.
  • herbicidal mixture partners are: Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6- (4-chloro- 2-fluoro-3-methylphenyl) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsubutazolin, beflazolin, ben- ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone
  • Flucarbazone flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -flufen-methyl, fluoroglycofen-sulfate, fluoroglycupsulfurate, flurupyr-methyl-sulfate, flurupyrupsulfate -sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-s
  • S1 compounds from the group of heterocyclic carboxylic acid derivatives: S1 a ) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1a), preferably compounds such as 1 - (2,4-Dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline 3-carboxylic acid ethyl ester (S1-1) ("Mefenpyr-diethyl”), and related compounds, as described in WO-A-91/07874; S1 b ) Derivatives of dichlorophenylpyrazole carboxylic acid (S1b), preferably compounds such as 1- (2,4-dichlorophenyl) -5-methyl
  • S2 a Compounds from the group of the 8-quinolinoxy derivatives (S2): S2 a ) Compounds of the 8-quinolinoxyacetic acid type (S2a), preferably (5-chloro-8-quinolinoxy) acetic acid (1-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-allyl-oxy-butyl ester (S2-3), (5-chloro-8-quinolinoxy) -acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy ) ethyl acetate (S2-5), (5-chloro-8-quinolinoxy) methyl acetate (S2-6), (5-chloro-8
  • S3 Active ingredients of the dichloroacetamide type (S3), which are often used as pre-emergence safeners (soil-acting safeners), such as.
  • B. "Dichlormid” (N, N-diallyl-2,2-dichloroacetamide) (S3-1), “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from the company Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl- 2H-1,4-benzoxazine) (S3-4), "PPG-1292” (N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide) from PPG Industries (S3
  • R B 3 halogen, 1C 1 -C 4 ) alkyl, (C1-C4) haloalkyl or (C1-C4) alkoxy and m B 1 or 2, for example those in which
  • R B 1 is cyclopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe
  • RB is cyclopropyl
  • R B 2 hydrogen
  • R B 3 5-Cl-2-OMe is (S4-2)
  • RB is ethyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe (S4-3)
  • Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cs) alkyl, (C3-Cs) cycloalkyl, (C3- C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
  • Rc 3 halogen, (C1-C4) alkyl, (C1-C4) alkoxy, CF 3 and m c 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea, 1- [4- (N-4 , 5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea;
  • RD 5 denotes 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.
  • S5 Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-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.
  • S6 Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • S7 Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), for example diphenylmethoxyacetic acid methyl ester (CAS Reg.Nr.41858-19-9) (S7-1), diphenylmethoxyacetic acid ethyl ester or diphenylmethoxyacetic acid as described in WO-A-98/38856.
  • S7-1 diphenylmethoxyacetic acid methyl ester
  • S7-1 diphenylmethoxyacetic acid ethyl ester
  • diphenylmethoxyacetic acid as described in WO-A-98/38856.
  • R D 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy
  • R D 2 is hydrogen or (C 1 -C 4 ) alkyl
  • R D 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, identical or different radicals from the group consisting of halogen and alkoxy; or their salts,
  • n D is an integer from 0 to 2.
  • Active ingredients from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones e.g. 1,2-dihydro-4-hydroxy-1- ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg.Nr .: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3- (5-tetrazolyl-carbonyl ) -2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
  • S11 Active ingredients of the type of oxyimino compounds (S11), which are known as seed dressings, such as. B. "Oxabetrinil” ((Z) -1,3-Dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as a seed dressing safener for millet against damage from metolachlor, "Fluxofenim” (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) oxime) (S11-2), which is used as a seed dressing safener for millet against damage from Metolachlor is known, and "Cyometrinil” or “CGA-43089” ((Z) -Cyanomethoxyimino (phenyl) acetonitrile) (S11-3), which is known as a seed dressing safener for millet against
  • S12 Active ingredients from the class of isothiochromanones (S12), such as methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg.No. 205121-04-6 ) (S12-1) and related compounds from WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): "Naphthalic anhydride” (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim” (4.6 -Dichlor-2-phenylpyrimidine) (S13-2) which is known as a safener for pretilachlor in sown rice, "Flurazole” (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13 -3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415” (CAS-Reg.Nr.31541-57-8) (4-Carboxy-3,4-dihydro-2H- 1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for
  • R H 1 is a (C1-C6) haloalkyl radical and R H 2 is hydrogen or halogen and R H 3, R H 4 independently of one another hydrogen, (C1-C16) alkyl, (C2-C16) alkenyl or (C 2 -C 16 ) alkynyl, where each of the last-mentioned 3 radicals is unsubstituted or by one or more radicals from the group halogen, hydroxy, cyano, ( C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylamino, di [(C 1 -C 4 ) alkyl] amino, [ (C 1 -C 4 ) alkoxy] carbon
  • Preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or their salts, in particular with the compounds of the formulas (1-1) to (1-68) and / or their salts are: cloquintocet-mexyl, cyprosulfamide, Fenchlorazole-ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Table A4 Post-emergence effects against Veronica persica (VERPE) Table A5: Post-emergence effects against Alopecurus myosuroides (ALOMY) Table A6: Post-emergence effects against Digitaria sanguinalis (DIGSA) Table A7: Post-emergence effects against Echinochloa crus-galli (ECHCG) Table A8: Post-emergence effects against Abutilon theophrasti (ABUTH)
  • Table A9 Post-emergence effects against Stellaria media (STEME)
  • the compounds according to the invention No. 1-1, 1-2, 1-3, 1-5, 1-6, 1-8, 1-9, 1-10, 1 -11, 1-12, 1-13, 1-14, 1-15, 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, 1-33, 1-34, 1-35, 1-46, 1-47, 1-48, 1-52, 1 -53, 1-55 and 1-56 with post-emergence treatment a very good herbicidal activity against the harmful plants Poa annua (POAAN), Amaranthus retroflexus (AMARE), Bassia scoparia (KCHSC), Veronica persica (VERPE), Alopecurus myosuroides (ALOMY ), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Ab
  • Table B1 Post-emergence effect against Amaranthus retroflexus (AMARE)
  • Table B2 Post-emergence effect against Polygonum convolvulus (POLCO)
  • Table B3 Post-emergence effects against Viola tricolor (VIOTR)
  • Table B4 Post-emergence effects against Veronica persica (VERPE) As the results of Tables B1-B4 show by way of example, the compounds Nos.
  • 1-2, 1-15, 1-20, 1-28, 1-32 and 1-34 have a very good herbicidal activity against post-emergence treatment the harmful plants Amaranthus retroflexus (AMARE), Polygonum convolvulus (POLCO), Viola tricolor (VIOTR) and Veronica persica (VERPE) at an application rate of 80 g of active ingredient per hectare.
  • AARE Amaranthus retroflexus
  • POLCO Polygonum convolvulus
  • VIOTR Viola tricolor
  • VERPE Veronica persica
  • C. Pre-emergence herbicidal action at 320 g / ha Seeds of monocotyledon and dicotyledon weed plants were laid out in plastic pots in sandy loam soil (double sowing with one species of monocotyledon or dicotyledon weed plants per pot) and covered with soil.
  • Tables C1 to C11 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 320 g / ha, which were obtained according to the aforementioned test procedure.
  • Table C1 Pre-emergence effects against Digitaria sanguinalis (DIGSA)
  • Table C2 Pre-emergence effects against Echinochloa crus-galli (ECHCG)
  • Table C3 Pre-emergence effects against Poa annua (POAAN)
  • Table C5 Pre-emergence effect against Amaranthus retroflexus (AMARE)
  • Table C6 Pre-emergence effects against Bassia scoparia (KCHSC)
  • KCHSC Pre-emergence effects against Matricaria inodora
  • Table C8 Pre-emergence effects against Stellaria media (STEME)
  • Table C9 Pre-emergence effects against Veronica persica (VERPE)
  • Table C10 Pre-emergence effects against Alopecurus myosuroides (ALOMY)
  • Table C11 Pre-emergence effects against Setaria viridis (SETVI)
  • Table D1 Pre-emergence effects against Digitaria sanguinalis (DIGSA)
  • Table D2 Pre-emergence effects against Setaria viridis (SETVI)
  • Table D3 Pre-emergence effects against Abutilon theophrasti (ABUTH)
  • Table D4 Pre-emergence effect against Amaranthus retroflexus (AMARE)
  • Table D5 Pre-emergence effects against Matricaria inodora (MATIN)
  • Table D6 Pre-emergence effect against Polygonum convolvulus (POLCO)
  • Table D7 Pre-emergence effects against Viola tricolor (VIOTR)
  • Table D8 Pre-emergence effects against Veronica persica (VERPE)
  • Table D1-D8 show by way of example, the compounds Nos.
  • 1-2, 1-5, 1-15, 1-20, 1-28, 1-32 and 1-34 show a very high degree of pre-emergence treatment good herbicidal activity against the harmful plants Digitaria sanguinalis (DIGSA), Setaria viridis (SETVI), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Matricaria inodora (MATIN), Polygonum convolvulus (POLCO), Viola tricolor (VIOTR.) and Veronica persica (VERPE) at an application rate of 80 g of active ingredient per hectare.
  • DIGSA Digitaria sanguinalis
  • SETVI Setaria viridis
  • ABUTH Abutilon theophrasti
  • AMARE Amaranthus retroflexus
  • MATIN Matricaria inodora
  • POLCO Polygonum convolvulus
  • Viola tricolor Viola tricolor
  • VERPE Veronica persica
  • Table E1 Herbicidal pre-emergence effects using the example of Abutilon theophrasti (ABUTH), Digitaria sanguinalis (DIGSA) and Echinochloa crus-galli (ECHCG). Comparison of compounds according to the invention with compounds from WO94 / 17059: As the results in Table E1 show, the compounds according to the invention Nos. 1-15, 1-34, 1-46 and 1-47 in comparison with those from the literature (WO94 / 17059 (Ex. No.

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Abstract

L'invention concerne des 3-(2-hétéroaryloxyphényl)isoxazolines substituées de formule générale (I) et leur utilisation comme herbicides, en particulier pour lutter contre les plantes adventices et/ou graminées adventices dans des cultures de plantes cultivées et/ou comme régulateurs de la croissance de plantes pour influencer la croissance de cultures de plantes cultivées. L'invention concerne également des agents herbicides et/ou de lutte contre la croissance de plantes comprenant un ou plusieurs composés de formule générale (I).
PCT/EP2020/072462 2019-08-13 2020-08-11 3-(2-hétéroaryloxyphényle)isoxazolines substituées, leurs sels et leur utilisation en tant que substances actives herbicides WO2021028419A1 (fr)

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EP0094349A2 (fr) 1982-05-07 1983-11-16 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
JPS6087270A (ja) 1983-09-26 1985-05-16 バイエル・アクチエンゲゼルシヤフト １，３‐ジアリール‐５‐メチレン‐パーヒドロピリミジン‐２‐オン
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WO2008131860A2 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridone-carboxamides, phytoprotecteurs contenant ces composés, procédés pour leur production et leur utilisation
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CN101838227A (zh) 2010-04-30 2010-09-22 孙德群 一种苯甲酰胺类除草剂的安全剂
WO2015089003A1 (fr) 2013-12-10 2015-06-18 E. I. Du Pont De Nemours And Company Composés herbicides de pyrimidinyloxybenzène substitués
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