WO2020245097A1 - Pyridinyloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides - Google Patents

Pyridinyloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides Download PDF

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WO2020245097A1
WO2020245097A1 PCT/EP2020/065162 EP2020065162W WO2020245097A1 WO 2020245097 A1 WO2020245097 A1 WO 2020245097A1 EP 2020065162 W EP2020065162 W EP 2020065162W WO 2020245097 A1 WO2020245097 A1 WO 2020245097A1
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alkyl
plants
general formula
compounds
methyl
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PCT/EP2020/065162
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German (de)
English (en)
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Michael Charles MCLEOD
David Michael BARBER
Ralf Braun
Harald Jakobi
Elisabeth ASMUS
Dirk Schmutzler
Anu Bheemaiah MACHETTIRA
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Bayer Aktiengesellschaft
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    • 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
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms

Definitions

  • the invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and grass weeds in crops of useful plants.
  • This invention specifically relates to substituted pyridinyloxypyridines and their salts, processes for their preparation and their use as herbicides.
  • Crops of useful plants or active ingredients for controlling unwanted vegetation sometimes have disadvantages when they are used, be it that they (a) have no or inadequate herbicidal activity against certain harmful plants, (b) an insufficient spectrum of harmful plants that can be controlled with an active ingredient can be, (c) too low selectivity in crops of useful plants and / or (d) have a toxicologically unfavorable profile.
  • some active ingredients which can be used as plant growth regulators in some useful plants lead to undesirably reduced yields in other useful plants or are incompatible with the cultivated plant, or only compatible with a narrow application rate range.
  • Some of the known active ingredients cannot be produced economically on an industrial scale because of the difficult accessibility of precursors and reagents, or they have insufficient chemical stabilities. With other active ingredients, the effect depends too much on environmental conditions, such as weather and soil conditions.
  • substituted pyridinyloxypyridines or their salts are particularly suitable as herbicidal active ingredients.
  • the present invention relates to pyridinyloxypyridines of the general formula (I) or salts thereof substituted therewith
  • R 1 represents hydrogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkenyl, (C 1 -C 4 ) -alkynyl or halogen, and
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, nitro, amino, hydroxy, cyano, halogen, formyl, carboxyl, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -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 ) -alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylthio- (C 1 -C 4 ) -al
  • 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. Suitable substituents which, in deprotonated form, such as sulfonic acids, determined
  • Sulfonic acid amides or carboxylic acids can form internal salts with groups that can in turn be protonated, such as amino groups. Salt formation can also be caused by the action of a base
  • 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 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
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • Alkyl sulfoxonium salts such as (C 1 -C 4 ) trialkylsulfonium and (C 1 -C 4 ) trialkylsulfoxonium salts.
  • substituted pyridinyloxypyridines of the general formula (I) according to the invention can, depending on external conditions, such as pH, solvent and temperature, possibly be present in various tautomeric structures, all of which are encompassed by the general formula (I).
  • Preferred subject matter of the invention are compounds of the general formula (I) in which R 1 is hydrogen, cyano, (C 1 -C 4 ) -alkyl or halogen, and
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, amino, hydroxy, cyano, halogen, formyl, carboxyl, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -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 ) -alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -halo
  • R 1 represents hydrogen, cyano, methyl or halogen
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, cyano, halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -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 ) -alkyl, (C 1 -C 4 ) -haloalkoxy- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -haloalkylcarbonyl, (C 1 -C 4
  • R 1 represents hydrogen or halogen
  • R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, halogen, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -haloalkoxy.
  • R 2 represents hydrogen, fluorine, chlorine, bromine, methyl or methoxy
  • R 3 represents hydrogen, chlorine or methyl
  • R 4 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy
  • R 5 represents hydrogen or methyl.
  • 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.
  • (but not limited to) (C 1 -C 4 ) -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.
  • the number of carbon atoms relates to the alkyl radical in the alkylcarbonyl group.
  • the number of C atoms relates to the alkyl radical in the alkoxy carbonyl group.
  • the number of C atoms relates to the alkyl radical in the alkylcarbonyloxy group.
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which (a) is preferably unsubstituted or (b) is mono- or polysubstituted and in the case of (b) is referred to as “substituted alkyl”. Preferred substituents are
  • Halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, methoxy, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • Haloalkyl denote by identical or different halogen atoms, partially or completely substituted alkyl, alkenyl or alkynyl, e.g. Monohaloalkyl
  • ( Monohaloalkyl) such as e.g. B. CH 2 CH 2 CI, CH 2 CH 2 Br, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as CCI 3, CCIF 2, CFCl 2 , CF 2 CClF 2, CF 2 CCIFCF 3 ; Polyhaloalkyl such as e.g. B. CH 2 CHFCl, CF 2 CClFH,
  • 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 CI; the same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4 ) -alkyl mentioned here by way of example means a shorthand notation for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to
  • Range 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.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including those in compound radicals, have the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • 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. Residues with a double bond or triple bond are preferred.
  • alkenyl also includes, in particular, straight-chain or branched open-chain ones
  • 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 cumulated double bonds, such as allenyl (1,2-propadienyl) and 1, 2-butadienyl.
  • Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, e.g.
  • (but not limited to) (C 2 -C 4 ) -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.
  • alkynyl also includes, in particular, straight-chain or branched open-chain ones
  • (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 (a) is preferably unsubstituted, or (b) by alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl,
  • Aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl is further substituted.
  • 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 [l .1.
  • (C3-C6) -cycloalkyl denotes a shorthand for cycloalkyl with three to 6 carbon atoms, corresponding to the range given for carbon atoms.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-6 carbon atoms, e.g. 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.
  • the explanations for substituted cycloalkyl apply accordingly.
  • alkylidene e.g. B. also in the form (C 1 -Cio) -Alkyliden, denotes the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • alkylidene e.g. B. also in the form (C 1 -Cio) -Alkyliden, denotes the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Alkoxyalkyl stands for an alkoxy radical bonded via an alkyl group and "Alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl stands for an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • ..Haloalkoxyalkyl stands for a bound haloalkoxy radical and ..Haloalkylthioalkyl means a haloalkylthio radical bonded 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. (but not limited to) 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, for example (but not limited to) trimethylsilyl, triethylsilyl.
  • 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.
  • the possible 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 derived from the
  • Preparation obtained mixtures obtained by customary separation methods The chromatographic separation can take place both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the production of 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.
  • the purification can also be done by
  • 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 and R 5 of the general formula (I) have the meanings defined above in the schemes below, provided that there are no exemplary but non-restrictive definitions.
  • the pyridinyloxypyridines of the general formula (I) can be prepared by substituting the pyridines (EI) in the presence of bases with the hydroxypyridine (E-II), LG being a leaving group (such as a halogen) (Scheme 1).
  • 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 acetonitrile, dimethylformamide, or 1-methyl -2-pyrrolidone, at temperatures between 0 ° C and the boiling point of the solvent.
  • the hydroxypyridines (E-II) can also be present as pyridone tautomers.
  • the halogenating reagent can be, for example, N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide.
  • the reactions are generally carried out in an organic solvent, such as, for example, acetonitrile or dimethylformamide, at temperatures between 0 ° C. and the boiling point of the solvent.
  • Synthesis stage 2 3-fluoro-2 - [(5-chloro-2-pyridyl) oxy] -5-nitro-pyridin-4-amine (table example no. 1-12)
  • a mixture of 2,3-dichloro-5-nitropyridin-4-amine (90 mg, 0.43 mmol), 5-fluoropyridin-2-ol (54 mg, 0.48 mmol) and cesium carbonate (280 mg, 0.87 mmol) in acetonitrile ( 5 ml) is heated at 80 ° C. for 7 h and then cooled to room temperature, diluted with water and extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered and concentrated. By subsequent column chromatographic purification of the resulting
  • the present invention also relates to the use of one or more
  • 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 a the embodiment characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-1) to (1-19) and / or their salts, in each case as defined above, or an agent according to the invention as defined below,
  • the present invention also relates to a method for controlling undesirable 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 (1-19) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below,
  • 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. grains, seeds or vegetative reproductive organs such as tubers or buds
  • 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 provides a method of combating
  • 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
  • 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 e.g. in pre-sowing (if necessary also by incorporation into the soil), pre-emergence and / or
  • 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:
  • Monocotyledon 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.
  • Harmful plants remain in the growth stage present at the time of application or die completely after a certain time, so that in this way competition from weeds that is harmful to the crop plants is eliminated very early and lastingly.
  • the compounds of the general formula (I) according to the invention have excellent herbicidal activity against monocotyledon and dicotyledon weeds, cultivated plants of economically important crops, e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Uactuca, Einum,
  • Plant ingredients 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. Because of their herbicidal and plant growth regulatory properties, 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, for example, 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, e.g. of grain such as wheat, barley, rye, oats, millet, rice and maize or crops of sugar beet, cotton, soy, rapeseed, potato, tomato, pea and other vegetables.
  • useful and ornamental plants e.g. of grain such as wheat, barley, rye, oats, millet, rice and maize or crops of sugar beet, cotton, soy, rapeseed, 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 usually characterized by particularly advantageous properties, for example by resistance to certain pesticides, especially certain ones
  • 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 concern e.g. the harvest in terms of quantity, quality, shelf life,
  • 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.
  • Other special properties can include tolerance or resistance to abiotic stressors e.g. Heat, cold, drought, salt and ultraviolet radiation lie.
  • the compounds of the general formula (I) can preferably be used as herbicides in
  • Crops of useful plants are used which are resistant to the phytotoxic effects of herbicides or which have been made resistant by genetic engineering.
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard procedures, e.g. Base exchanges carried out, partial sequences removed or natural or synthetic sequences added. For connecting the DNA fragments
  • RNA for example, achieved by expressing at least one corresponding antisense RNA, one sense RNA to achieve a cosuppression effect or expressing at least one appropriately constructed ribozyme that specifically cleaves transcripts of the abovementioned gene product.
  • DNA molecules can be used that include the entire coding sequence of a gene product including any flanking sequences that may be present, as well as DNA molecules that only include parts of the coding sequence, these parts having to be long enough to be in the cells to bring about 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 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.
  • transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can be any plant
  • the compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are resistant to growth substances such as e.g. Dicamba or against herbicides which contain 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, glyphosates, glufosinates or benzoylisoxazoles 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 for 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.
  • Pre- or post-emergence use of compounds of the general formula (I) in soy is also preferred.
  • the use of the compounds of the formula (I) according to the invention for controlling 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 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 those identified as preferred or particularly preferred
  • 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 other growth regulators,
  • component (i) of an agent according to the invention are preferably selected from the group of substances listed in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • 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 Group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, carriers solid at 25 ° C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably Organic solvents that are miscible with water in any ratio at 25 ° C and 1013 mbar.
  • formulation auxiliaries ii) which are customary in crop protection and selected from Group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, carriers solid at 25 ° C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants
  • 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 which biological and / or chemico-physical parameters are given. Possible formulation options include, for example:
  • WP Wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • CS Capsule suspensions
  • DP dusts
  • dressings granulates for the litter
  • granules in the form of micro, spray, lift and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • Wettable powders are preparations that are uniformly dispersible in water, which in addition to the active ingredient, in addition to a diluent or inert substance, also surfactants of an ionic and / or nonionic type (wetting agents,
  • Dispersants for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, lignin sulfonic acid Sodium, 2,2'-dinaphthylmethane-6,6'-disulphonic acid, sodium dibutylnaphthalene-sulphonic acid or sodium oleoylmethyltauric acid.
  • 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 made by dissolving the active ingredient in an organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of an ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or also higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of an ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid ester or
  • Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene sorbitan fatty acid ester.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and, if necessary, addition of surfactants, such as are e.g. are already listed above for the other formulation types.
  • Emulsions e.g. Oil-in-water emulsions (EW), for example by means of stirrers,
  • Solvents and optionally surfactants such as are e.g. are already listed above for the other formulation types.
  • Granules can be produced either by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carrier materials such as sand, kaolinite or granulated inert material. Can also be appropriate
  • Active ingredients are 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 e.g. about 10 to 90% by weight, the remainder to 100% by weight consists of conventional formulation components. In the case of emulsifiable concentrates, the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dusty
  • 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 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 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 be, e.g. as a ready-made 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. of Chemistry, 2012 and the literature cited there.
  • inventive compounds (I) of particular interest which the compounds of general formula (I) or their combinations with other herbicides or pesticides and
  • Safeners included.
  • the safeners which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as grain (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soy, preferably grain.
  • the weight ratio of herbicide (mixture) to safener generally depends on the
  • the application rate of the herbicide and the effectiveness of the respective safener 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 mixtures thereof with other herbicides / pesticides and as
  • Ready-made formulation or tank mix with the herbicides can be provided and applied.
  • the herbicide or herbicide-safener formulations in commercially available form are optionally diluted 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.
  • the application rate 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 both to the application in
  • the application as a stalk shortener can take place in different stages of the growth of the plants. For example, use after tillering at the beginning of the
  • the treatment of the seed which includes the different seed dressing and coating techniques, is also possible.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • Combination partners for the compounds of the general formula (I) according to the invention in agents according to the invention are, for example, known active ingredients which act on the 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 based 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.
  • Known herbicides or plant growth regulators that can be combined with the compounds according to the invention are mentioned below by way of example, these active ingredients either with their "common name" in the English-language variant according to the International Organization for Standardization (ISO) or with the chemical name or code number are designated.
  • ISO International Organization for Standardization
  • herbicidal mixing partners are:
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenolofen-butyl, flurenol, flurenolofen-butyl, -dimethylammonium and -fluoroglycethylammonium flupyrsulfuron, flupyrsul Workshopon-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate-, glufosinuf-ammonate, glufosinate
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • met.zthiazuron methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron-ester, monosulfuron, ie, N- [3-chloron, monosulfuron -4- (1-methylethyl) -phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargy
  • plant growth regulators as possible mixing partners are:
  • Brassinolide Catechin, chlormequat Chloride, cloprop, cyclanilide, 3- (Cycloprop-l-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probemonic acid azole, jasmonic acid , maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2- (l-naphthyl)
  • Salicylic acid strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
  • S1 c derivatives of 1, 5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as
  • S1 d compounds of the triazole carboxylic acid type (S1 d ), preferably compounds such as
  • Fenchlorazole ethyl ester
  • ethyl ester i. l- (2,4-Dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3-carboxylic acid ethyl ester (Sl-7), and related compounds, as described in EP-A-174562 and EP- A-346620;
  • S1 e compounds of the 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e ), preferably compounds such as
  • S2 a compounds of the 8-quinolineoxyacetic acid type (S2 a ), preferably
  • S2 b compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ), preferably
  • oils effective safeners are used, such as. B.
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2)
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl- l, 3-oxazobdin) 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
  • TI-35 (1-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
  • V A is 0, 1, 2 or 3;
  • R B 1 , R B 2 independently of one another hydrogen, (C 1 -C 6 ) alkyl (C 3 -C 6 ) cycloalkyl, (C 3 -
  • R B 3 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkoxy and
  • n B 1 or 2
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-2)
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-4) and
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe (S4-5);
  • R C 1 , R C 2 independently of one another hydrogen, (C 1 -C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -
  • R C 3 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 and
  • mc 1 or 2;
  • R D 4 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
  • R D 5 hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -
  • Carboxylic acid derivatives (S5) e.g.
  • S7 compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g.
  • 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 by one or more , preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; or their salts,
  • n D is an integer from 0 to 2.
  • R E 1 halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
  • n E is an integer from 0 to 4,
  • R E 2 (C 1 -C 16 ) alkyl, (C 2 -C 6 -alkenyl. (C 3 -C) cycloalkyl, aryl; benzyl, halobenzyl,
  • R E 3 is hydrogen or (C 1 -C 6 ) alkyl.
  • 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) acetonitril) (S11-1), which is known as a seed dressing safener for millet against damage from metolachlor,
  • S12 Active ingredients from the class of isothiochromanones (S12), such as e.g. Methyl [(3 -oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S 12-1) and related compounds from WO-A -1998/13361.
  • S12 isothiochromanones
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic acid anhydride) (S 13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
  • Cyanamide which is known as a safener for corn against damage from imidazolinones
  • MG 191 (CAS Reg.Nr. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize,
  • CSB (1-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.
  • R H 1 denotes a (C 1 -C 6 ) haloalkyl radical
  • R H 2 is hydrogen or halogen
  • R H 3 , R H 4 independently of one another are hydrogen, (C 1 -C 16 ) alkyl, (C 2 -C 16 ) alkenyl or
  • each of the last-mentioned 3 radicals is unsubstituted or substituted by one or more radicals from the group consisting of 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] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6 ) cycloalkyl. that is unsubstituted or substituted, phenyl that is unsubstituted or substituted, and heterocyclyl that is unsubstituted or substituted, is substituted,
  • each of the last-mentioned 4 radicals is unsubstituted or substituted by one or more radicals from the group consisting of halogen, hydroxy, cyano, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (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] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl,
  • R H 3 is (C 1 -C 4 ) -alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C) alkynyloxy or (C 2 -C 4 ) haloalkoxy and
  • R H 4 is hydrogen or (C 1 -C 4 ) -alkyl or
  • heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S and which is 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 ) alkylthio is substituted.
  • 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 (1-19) 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.
  • Tables A1 to A12 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 1280 g / ha, which were obtained according to the aforementioned test procedure.
  • Table A6 Post-emergence effect against Amaranthus retroflexus (AMARE)
  • Table A7 Post-emergence effects against Matricaria inodora (MATIN)
  • Tables B1 to B8 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 B7 Post-emergence effects against Viola tricolor (VIOTR)
  • Table B8 Post-emergence effects against Veronica persica (VERPE)
  • Alopecurus myosuroides Alopecurus myosuroides
  • Echinochloa crus-galli Echinochloa crus-galli
  • SETVI Setaria viridis
  • AMARE Amaranthus retroflexus
  • POLCO Polygonum convolvulus
  • Viola tricolor VIOTR
  • Veronica persica Viola tricolor
  • VERPE Veronica persica
  • Tables CI to C12 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 1280 g / ha, which were obtained according to the aforementioned test procedure.
  • Table C3 Pre-emergence effects against Poa annua (POAAN)
  • Table C 4 Pre-emergence effects against Setaria viridis (SETVI)
  • Table C7 Pre-emergence effects against Matricaria inodora (MATIN)
  • Table C8 Pre-emergence effects against Stellaria media (STEME)
  • Table CIO Pre-emergence effects against Digitaria sanguinalis (DIGSA)
  • DIGSA Digitaria sanguinalis
  • KCHSC Bassia scoparia
  • Seeds of monocotyledonous and dicotyledonous weeds and cultivated plants were placed in plastic or organic plant pots and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the covering soil as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of the equivalent of 600 l / ha.
  • WP wettable powders
  • EC emulsion concentrates
  • Tables D1 to D12 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 D7 Pre-emergence effect against Amaranthus retroflexus (AMARE)
  • Table D8 Pre-emergence effects against Matricaria inodora (MATIN)
  • Table D12 Pre-emergence effects against Veronica persica (VERPE) As the results of Tables Dl -Dl 2 show by way of example, the inventive
  • Alopecurus myosuroides Alopecurus myosuroides
  • DIGSA Digitaria sanguinalis
  • EHCG Echinochloa crus-galli
  • LRLRI Lolium rigidum
  • SETVI Setaria viridis
  • ABUTH Abutilon theophrasti
  • AMARE Amaranthus retroflexus
  • MATIN Matricaria inodora
  • Pharbitis purpurea PMBPU
  • POLCO Polygonum convolvulus
  • VIP Viola tricolor
  • VERPE Veronica persica

Abstract

L'invention concerne des pyridinyloxypyridines substituées représentées par la formule générale (I) et leur utilisation comme herbicides, en particulier pour lutter contre les plantes adventices et/ou les graminées indésirables dans des cultures de plantes utiles et/ou comme régulateurs de croissance des plantes pour influencer la croissance des cultures de plantes utiles. La présente invention concerne en outre des agents herbicides et/ou régulateurs de croissance de plantes comprenant un ou plusieurs composés de formule générale (I).
PCT/EP2020/065162 2019-06-04 2020-06-02 Pyridinyloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides WO2020245097A1 (fr)

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WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005112630A1 (fr) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Derives de quinoxalin-2-one, phytoprotecteurs pour plantes utiles contenant ces derives, procede de production et utilisation desdits derives
WO2007023764A1 (fr) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits
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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
WO2015086519A1 (fr) 2013-12-09 2015-06-18 Ucb Biopharma Sprl Dérivés d'imidazopyridine comme modulateurs de l'activité du tnf

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US3429689A (en) 1964-02-10 1969-02-25 Ciba Ltd Phenoxy pyridines as herbicides
US4394159A (en) 1978-07-15 1983-07-19 Celamerck Gmbh & Co. Kg 2-Chloro-3-(phenoxy or phenylthio)-6-6-nitro -anilines
EP0086750A2 (fr) 1982-02-17 1983-08-24 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0094349A2 (fr) 1982-05-07 1983-11-16 Ciba-Geigy Ag Utilisation de dérivés de quinoléine pour protéger des plantes cultivées
US4493730A (en) 1982-09-10 1985-01-15 Ishihara Sangyo Kaisha, Ltd. Phenoxypyridine useful as a herbicide
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
EP0174562A2 (fr) 1984-09-11 1986-03-19 Hoechst Aktiengesellschaft Agents pour la protection de plantes basés sur des dérivés de 1,2,4- briazole ainsi que dérivés 1,2,4-triazole
EP0191736A2 (fr) 1985-02-14 1986-08-20 Ciba-Geigy Ag Utilisation de dérivés de la quinoléine pour la protection de plantes cultivables
EP0269806A1 (fr) 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
EP0268554A2 (fr) 1986-10-22 1988-05-25 Ciba-Geigy Ag Dérivés d'acide diphényl-1,5-pyrazol-3-carbonique pour la protection de plantes de culture
EP0333131A1 (fr) 1988-03-17 1989-09-20 Hoechst Aktiengesellschaft Agent de protection des plantes à base de dérivés d'acide pyrazolcarboxylique
EP0346620A1 (fr) 1988-05-20 1989-12-20 Hoechst Aktiengesellschaft Agents phytoprotecteurs contenant des dérivés du 1,2,4-triazole ainsi que dérivés du 1,2,4-triazole
EP0365484A1 (fr) 1988-10-20 1990-04-25 Ciba-Geigy Ag Sulfamoylphénylurées
WO1991008202A1 (fr) 1989-11-25 1991-06-13 Hoechst Aktiengesellschaft Isoxazolines, procede de preparation et application comme produits phytosanitaires
WO1991007874A1 (fr) 1989-11-30 1991-06-13 Hoechst Aktiengesellschaft Pyrazoline pour la protection de plantes cultivees contre les herbicides
EP0492366A2 (fr) 1990-12-21 1992-07-01 Hoechst Schering AgrEvo GmbH Nouveaux dérivés de chloro-5-quinoline-8-acide oxyalkanecarboniques, procédé pour leur préparation et leur utilisation comme antidote d'herbicides
EP0582198A2 (fr) 1992-08-01 1994-02-09 Hoechst Schering AgrEvo GmbH Composés (hétéro-)aryliques substitués, procédé pour leur préparation, compositions les contenant et leur utilisation comme agents de protection
WO1995007897A1 (fr) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Isoxazolines substituees, leur procede de preparation, agents les contenant et leur utilisation comme reducteurs de phytotoxicite
WO1997045016A1 (fr) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Nouveaux n-acylsulfonamides, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998013361A1 (fr) 1996-09-26 1998-04-02 Novartis Ag Composition herbicide
WO1998027049A1 (fr) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Nouveaux derives d'acide 2-fluoroacrylique, nouveaux melanges d'herbicides et d'antidotes et leur utilisation
WO1998038856A1 (fr) 1997-03-04 1998-09-11 Zeneca Limited Compositions pour proteger du riz contre l'acetochlore
WO1999000020A1 (fr) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-tetrazolylcarbonyle)-2-quinolones et produits phytosanitaires pour plantes utiles les contenant
WO1999016744A1 (fr) 1997-09-29 1999-04-08 Aventis Cropscience Gmbh Amides d'acide benzoique d'acylsulfamoyle, agents phytosanitaires les contenant et procede permettant de les preparer
WO2002034048A1 (fr) 2000-10-23 2002-05-02 Syngenta Participations Ag Compositions agrochimiques avec des phytoprotecteurs a base de quinoline
WO2004084631A1 (fr) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Utilisation de composés aromatiques hydroxy comme phytoprotecteurs
WO2005015994A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Utilisation d'aromates hydroxy comme phytoprotecteurs
WO2005016001A1 (fr) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques
WO2005112630A1 (fr) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Derives de quinoxalin-2-one, phytoprotecteurs pour plantes utiles contenant ces derives, procede de production et utilisation desdits derives
WO2007023719A1 (fr) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire l'attaque chimique et composition herbicide produisant une attaque chimique réduite
WO2007023764A1 (fr) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent servant à réduire les effets nocifs d’un herbicide et composition d’herbicide ayant des effets nocifs réduits
WO2008131860A2 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridone-carboxamides, phytoprotecteurs contenant ces composés, procédés pour leur production et leur utilisation
WO2008131861A1 (fr) 2007-04-30 2008-11-06 Bayer Cropscience Ag Utilisation de pyridin-2-oxy-3-carbonamides comme phytoprotecteurs
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
WO2015086519A1 (fr) 2013-12-09 2015-06-18 Ucb Biopharma Sprl Dérivés d'imidazopyridine comme modulateurs de l'activité du tnf

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