WO2020245097A1 - Substituted pyridinyloxypyridines and salts thereof and use thereof as herbicidal agents - Google Patents

Substituted pyridinyloxypyridines and salts thereof and use thereof as herbicidal agents 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)
French (fr)
Inventor
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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Publication of WO2020245097A1 publication Critical patent/WO2020245097A1/en

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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

The invention relates to substituted pyridinyloxypyridines of general formula (I) and the use thereof as herbicides, in particular for controlling weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The invention further relates to herbicidal and/or plant growth-regulating agents comprising one or more compounds of general formula (I).

Description

Substituierte Pyridinyloxypyridine sowie deren Salze und ihre Verwendung als herbizide Wirkstoffe Substituted pyridinyloxypyridines and their salts and their use as herbicidal active ingredients
Beschreibung description
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsem in Nutzpflanzenkulturen. 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.
Speziell betrifft diese Erfindung substituierte Pyridinyloxypyridine sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. This invention specifically relates to substituted pyridinyloxypyridines and their salts, processes for their preparation and their use as herbicides.
Bisher bekannte Pflanzenschutzmittel zur selektiven Bekämpfung von Schadpflanzen in So far known pesticides for the selective control of harmful plants in
Nutzpflanzenkulturen oder Wirkstoffe zur Bekämpfung von unerwünschtem Pflanzenwuchs weisen bei ihrer Anwendung teilweise Nachteile auf, sei es, dass sie (a) keine oder aber eine unzureichende herbizide Wirkung gegen bestimmte Schadpflanzen, (b) ein zu geringes Spektrum der Schadpflanzen, das mit einem Wirkstoff bekämpft werden kann, (c) zu geringe Selektivität in Nutzpflanzenkulturen und/oder (d) ein toxikologisch ungünstiges Profil besitzen. Weiterhin führen manche Wirkstoffe, die als Pflanzenwachstumsregulatoren bei einigen Nutzpflanzen eingesetzt werden können, bei anderen Nutzpflanzen zu unerwünscht verminderten Emteerträgen oder sind mit der Kulturpflanze nicht oder nur in einem engen Aufwandmengenbereich verträglich. Einige der bekannten Wirkstoffe lassen sich wegen schwer zugänglicher Vorprodukte und Reagenzien im industriellen Maßstab nicht wirtschaftlich hersteilen oder besitzen nur unzureichende chemische Stabilitäten. Bei anderen Wirkstoffen hängt die Wirkung zu stark von Umweltbedingungen, wie Wetter- und Bodenverhältnissen ab. 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. Furthermore, 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.
Die herbizide Wirkung dieser bekannten Verbindungen, insbesondere bei niedrigen Aufwandmengen, bzw. deren Verträglichkeit gegenüber Kulturpflanzen bleibt verbesserungswürdig. The herbicidal action of these known compounds, especially when low amounts are used, or their compatibility with crop plants, remains in need of improvement.
In US4493730 und US3429689 sind verschiedene Phenoxypyridine als Herbizide beschrieben. Daneben werden in US4394159 2-Chlor-3-phenoxy-6-nitroaniline als Herbizide beschrieben. In US4493730 and US3429689 various phenoxypyridines are described as herbicides. In addition, US4394159 describes 2-chloro-3-phenoxy-6-nitroanilines as herbicides.
Pyridinyloxypyridine oder deren Salze, sowie deren Verwendung als herbizide Wirkstoffe sind dagegen noch nicht beschrieben. Pyridinyloxypyridines or their salts, and their use as herbicidal active ingredients, on the other hand, have not yet been described.
Überraschenderweise wurde nun gefunden, dass substituierte Pyridinyloxypyridine oder deren Salze als herbizide Wirkstoffe besonders gut geeignet sind. Gegenstand der vorliegenden Erfindung sind damit substituierte Pyridinyloxypyridine der allgemeinen Formel (I) oder deren Salze Surprisingly, it has now been found that 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
Figure imgf000003_0001
Figure imgf000003_0001
worin wherein
R1 für Wasserstoff, Cyano, (C1-C4)-Alkyl, (C1-C6)-Cycloalkyl, (C1-C4)-Haloalkyl, (C1-C4)-Alkenyl, (C1-C4)-Alkynyl oder Halogen steht, und 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
R2, R3, R4 und R5 unabhängig voneinander für Wasserstoff, Nitro, Amino, Hydroxy, Cyano, Halogen, Formyl, Carboxyl, (C1-C4)-Alkyl, (C1-C4)-Haloalkyl, (C1-C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C4)-Alkynyl, (C2-C4)-Haloalkynyl, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)-Haloalkoxy-(C1-C4)-alkyl, (C1-C4)-Alkylthio-(C1-C4)-alkyl, (C1-C4)-Alkylsulfmyl- (C1-C4)-alkyl, (C1-C4)-Alkylsulfonyl-(C1-C4)-alkyl, (C1-C4)-Alkylcarbonyl, (C1-C4)- Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbxnyl, (C1-C4)-Alkoxycarbonyl, (C2-C4)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (C2-C4)-Alkylaminocarbonyl, (C2-C)- Dialkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, (C1-C4)-Alkoxy, (C1-C4)-Haloalkoxy, (C1-C4)-Cycloalkoxy, (C1-C4)-Alkylcarbonyloxy, (C1-C4)-Haloalkylcarbonyloxy, (C1-C4)- Alkylamino, (C2-C6)-Dialkylamino, Formylamino, (C1-C4)-Alkylcarbonylamino, (C1-C4)- Haloalkylcarbonylamino, (C1-C4)-Alkoxycarbonylamino, (C1-C4)-Alkylsulfonylamino, (C1-C4)- Alkylthio, (C1-C4)-Haloalkylthio, (C3-C4)-Cycloalkylthio, (C1-C4)-Alkylsulfinyl, (C1-C4)- Haloalkylsulfinyl, (C3-C4)-Cycloalkylsulfinyl, (C1-C4)-Alkylsulfonyl, (C1-C4)- Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (C1-C4)-Alkylaminosulfonyl, (C2-C)- Dialkylaminosulfonyl oder (C1-C)-Trialkylsilyl stehen. 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 ) -alkyl, (C 1 -C 4 ) -alkylsulfmyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkylsulfonyl- (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -Alkylcarbonyl, (C 1 -C 4 ) - haloalkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbxnyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 2 -C 4 ) -haloalkoxycarbonyl, (C 3 -C 6 ) -cycloalkoxycarbonyl, (C 2 -C 4 ) -alkylaminocarbonyl, (C 2 -C) -dialkylaminocarbonyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl, (C 1 -C 4 ) -alkoxy, ( C 1 -C 4) -haloalkoxy, (C 1 -C 4) cycloalkoxy, (C 1 -C 4) alkylcarbonyloxy, (C 1 -C 4) -Haloalkylcarbonyloxy, (C 1 -C 4) - alkylamino, ( C 2 -C 6 ) -dialkylamino, formylamino, (C 1 -C 4 ) -alkylcarbonylam ino, (C 1 -C 4 ) - haloalkylcarbonylamino, (C 1 -C 4 ) -alkoxycarbonylamino, (C 1 -C 4 ) -alkylsulfonylamino, (C 1 -C 4 ) - alkylthio, (C 1 -C 4 ) - Haloalkylthio, (C 3 -C 4 ) -cycloalkylthio, (C 1 -C 4 ) -alkylsulfinyl, (C 1 -C 4 ) - haloalkylsulfinyl, (C 3 -C 4 ) -cycloalkylsulfinyl, (C 1 -C 4 ) - Alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, (C 1 -C 4 ) -alkylaminosulfonyl, (C 2 -C) -dialkylaminosulfonyl or (C 1 -C) -trialkylsilyl .
Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten The compounds of general formula (I) can by addition of a suitable
anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H3PO4oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p- Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren, bestimmte 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
Sulfonsäureamide oder Carbonsäuren, vorhegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salzbildung kann auch durch Einwirkung einer Base auf Sulfonic acid amides or carboxylic acids, if present, 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
Verbindungen der allgemeinen Formel (I) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkali- oder Compounds of general formula (I) take place. Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium and
Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der azide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Potassium hydroxide, sodium and potassium carbonate, and sodium and potassium hydrogen carbonate. These 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
Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre Ammoniumsalze, zum Beispiel mit Kationen der Formel 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
[NRaRbRcRd]+, worin Ra bis Rd jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Arylalkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und [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
Alkylsulfoxoniumsalze, wie (C1-C4)-Trialkylsulfonium- und (C1-C4)-Trialkylsulfoxoniumsalze. Alkyl sulfoxonium salts such as (C 1 -C 4 ) trialkylsulfonium and (C 1 -C 4 ) trialkylsulfoxonium salts.
Die erfmdungsgemäßen substituierten Pyridinyloxypyridine der allgemeinen Formel (I) können in Abhängigkeit von äußeren Bedingungen, wie pH-Wert, Lösungsmittel und Temperatur eventuell in verschiedenen tautomeren Strukturen vorliegen, die alle von der allgemeinen Formel (I) umfasst sind. The 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).
Im Folgenden werden die erfmdungsgemäßen Verbindungen der Formel (I) und ihre Salze auch als "Verbindungen der allgemeinen Formel (I)" bezeichnet. 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)".
Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin R1 für Wasserstoff, Cyano, (C1-C4)-Alkyl oder Halogen steht, und 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
R2, R3, R4 und R5 unabhängig voneinander für Wasserstoff, Amino, Hydroxy, Cyano, Halogen, Formyl, Carboxyl, (C1-C4)-Alkyl, (C1-C4)-Haloalkyl, (C1-C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)- Haloalkenyl, (C2-C4)-Alkynyl, (C2-C4)-Haloalkynyl, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)- Haloalkoxy-(C1-C4)-alkyl, (C1-C4)-Alkylcarbonyl, (C1-C4)-Haloalkylcarbonyl, (C1-C4)- Alkoxycarbonyl, (C2-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (C1-C4)-Alkoxy, (C1-C4)-Haloalkoxy, (C1-C4)-Cycloalkoxy, (C1-C4)-Alkylcarbonyloxy, (C1-C4)- Haloalkylcarbonyloxy, (C1-C4)-Alkylthio, (C1-C4)-Haloalkylthio, (C1-C4)-Alkylsulfinyl, (C1-C4)-Haloalkylsulfmyl, (C3-C4)-Cycloalkylsulfmyl, (C1-C4)-Alkylsulfonyl, (C1-C4)- Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (C1-C4)-Alkylaminosulfonyl oder (C1-C)- Trialkylsilyl stehen. 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 ) -haloalkylcarbonyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 2 -C 4 ) -alkylaminocarbonyl, (C 2 -C 6 ) -dialkylaminocarbonyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -cycloalkoxy, (C 1 -C 4 ) -alkylcarbonyloxy, (C 1 -C 4 ) -haloalkylcarbonyloxy, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio, (C 1 -C 4 ) -alkylsulfinyl, (C 1 -C 4 ) -haloalkylsulfmyl, (C 3 -C 4 ) -cycloalkylsulfmyl, (C 1 -C 4 ) -alkylsulfonyl, (C 1 -C 4 ) - Haloalkylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, (C 1 -C 4 ) -alkylaminosulfonyl or (C 1 -C) -trialkylsilyl.
Besonders bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff, Cyano, Methyl oder Halogen steht, und R 1 represents hydrogen, cyano, methyl or halogen, and
R2, R3, R4 und R5 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (C1-C4)-Alkyl, (C1-C4)- Haloalkyl, (C1-C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C4)-Alkynyl, (C2-C4)-Haloalkynyl, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)-Haloalkoxy-(C1-C4)-alkyl, (C1-C4)- Alkylcarbonyl, (C1-C4)-Haloalkylcarbonyl, (C1-C4)-Alkoxycarbonyl, (C2-C4)- Alkylaminocarbonyl, (C2-C)-Dialkylaminocarbonyl, (C1-C4)-Alkoxy, (C1-C4)-Haloalkoxy, (C1-C4)-Cycloalkoxy, (C1-C4)-Alkylthio oder (C1-C4)-Haloalkylthio stehen. 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 ) -Alkoxycarbonyl, (C 2 -C 4 ) -alkylaminocarbonyl, (C 2 -C) -dialkylaminocarbonyl, (C 1 -C 4 ) -alkoxy, (C 1 -C 4 ) -haloalkoxy, ( C 1 -C 4 ) -cycloalkoxy, (C 1 -C 4 ) -alkylthio or (C 1 -C 4 ) -haloalkylthio.
Ganz besonders bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Very particularly preferred subject matter of the invention are compounds of the general formula (I) in which
R1 für Wasserstoff oder Halogen steht, und R 1 represents hydrogen or halogen, and
R2, R3, R4 und R5 unabhängig voneinander für Wasserstoff, Halogen, (C1-C4)-Alkyl, (C1-C4)-Haloalkyl, (C1-C4)-Alkoxy oder (C1-C4)-Haloalkoxy stehen. 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.
Äußerst bevorzugter Erfmdungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin R1 für Wasserstoff oder Chlor steht, Extremely preferred subject matter of the invention are compounds of the general formula (I) in which R 1 represents hydrogen or chlorine,
R2 für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Methoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, methyl or methoxy,
R3 für Wasserstoff, Chlor oder Methyl steht, R4 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl oder Methoxy steht, und R 3 represents hydrogen, chlorine or methyl, R 4 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, and
R5 für Wasserstoff oder Methyl steht. R 5 represents hydrogen or methyl.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinenFormel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können The general or preferred 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
untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. can be combined as desired with one another, i.e. also between the specified preferred ranges.
Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herste llbarkeit sind erfmdungsgemäße Verbindungen der genannten allgemeinen Formel (I) oder deren Salze bzw. deren erfmdungsgemäße Verwendung von besonderem Interesse, worin einzelne Reste eine der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen kombiniert auftreten. Mainly for reasons of higher herbicidal activity, better selectivity and / or better producibility, compounds of the general formula (I) according to the invention or their salts or their use according to the invention, in which individual radicals are one of those already mentioned or below, are of particular interest have preferred meanings mentioned, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
Im Hinblick auf die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: With regard to the compounds of the general formula (I) according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and have in particular the meanings explained below:
Sofern nicht anders definiert, gilt generell für die Bezeichnung von chemischen Gruppen, dass die Anbindung an das Gerüst bzw. den Rest des Moleküls über das zuletzt genannte Strukturelement der betreffenden chemischen Gruppe erfolgt. Unless otherwise defined, 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.
Erfmdungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 4 Kohlenstoffatomen, z.B. (aber nicht beschränkt auf) (C1-C4)-Alkylsulfonyl wie Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1- Methylethylsulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1,1- Dimethylethylsulfonyl . According to the invention, "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.
Erfmdungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 4 Kohlenstoffatomen, wie (C1-C4)- Alkylthio, z.B. (aber nicht beschränkt auf) (C1-C4)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1- Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methylpropylthio, 1,1-Dimethylethylthio. ..Alkylsulfinyl (Alkyl-S(=O)-)“, soweit nicht an anderer Stelle anders definiert steht erfmdungsgemäß für Alkylreste, die über -S(=O)- an das Gerüst gebunden sind, wie (C1-C4)-Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (C1-C4)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1- Methylethylsulfinyl, Butylsulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1,1- Dimethylethylsulfinyl . According to the invention, "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 (alkyl-S (= O) -) ", unless otherwise defined, stands according to the invention for alkyl radicals that are bonded to the skeleton via -S (= O) -, such as (C 1 -C 4 ) -Alkylsulfinyl, e.g. B. (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“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (C1-C4)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2- Methylpropoxy , 1 , 1 -Dimethylethoxy . “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.
„Alkylcarbonyl“ (Alkyl-C(=O)-), soweit nicht an anderer Stelle anders definiert, steht erfmdungsgemäß für Alkylreste, die über -C(=O)- an das Gerüst gebunden sind, wie (C1-C4)-Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonylgruppe. "Alkylcarbonyl" (alkyl-C (= O) -), unless otherwise defined, according to the invention stands for alkyl radicals that are bonded to the skeleton via -C (= O) -, such as (C 1 -C 4 ) -Alkylcarbonyl. The number of carbon atoms relates to the alkyl radical in the alkylcarbonyl group.
„Alkoxycarbonyl (Alkyl-O-C(=O)-)“, soweit nicht an anderer Stelle anders definiert: Alkylreste, die über -O-C(=O)- an das Gerüst gebunden sind, wie (C1-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxy carbonylgruppe. "Alkoxycarbonyl (alkyl-OC (= O) -)", unless otherwise defined elsewhere: alkyl radicals that are attached to the structure via -OC (= O) -, such as (C 1 -C 4 ) -alkoxycarbonyl. The number of C atoms relates to the alkyl radical in the alkoxy carbonyl group.
Der Begriff„Alkylcarbonyloxy“ (Alkyl-C(=O)-O-) steht erfmdungsgemäß, soweit nicht an anderer Stelle anders definiert, für Alkylreste, die über eine Carbonyloxygruppe (-C(=O)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C1-C10)-, (C1-C)- oder (C1-C4)-Alkylcarbonyloxy. Die Anzahl der C- Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonyloxygruppe. The term “alkylcarbonyloxy” (alkyl-C (= O) -O-) stands according to the invention, unless otherwise defined, for alkyl radicals connected to the oxygen via a carbonyloxy group (-C (= O) -0-) the skeleton are bound, such as (C 1 -C 10 ) -, (C 1 -C) - or (C 1 -C 4 ) -alkylcarbonyloxy. The number of C atoms relates to the alkyl radical in the alkylcarbonyloxy group.
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder Iod. Wird die The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. Will the
Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder Iodatom. When the term is used for a radical, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.
Erfmdungsgemäß bedeutet„Alkyl“ einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der (a) bevorzugt unsubstituiert ist, oder (b) ein- oder mehrfach substituiert ist und im Fall von (b) als„substituiertes Alkyl“ bezeichnet wird. Bevorzugte Substituenten sind According to the invention, “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
Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder Iod. Halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, methoxy, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
„Haloalkyl“, ,,-alkenyl“ und ,,-alkinyl“ bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl "Haloalkyl", "- alkenyl" and "- alkynyl" denote by identical or different halogen atoms, partially or completely substituted alkyl, alkenyl or alkynyl, e.g. Monohaloalkyl
(= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z.B. CCI3, CCIF2, CFCl2,CF2CClF2, CF2CCIFCF3; Polyhaloalkyl wie z. B. CH2CHFCl, CF2CClFH, (= 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,
CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also includes the term perfluoroalkyl.
„Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. “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.
Der hier beispielhaft genannte Ausdruck "(C1-C4)-Alkyl" bedeutet eine Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der The term "(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
Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1-Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(C1-C6)-Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. 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.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1,3-Dimethylbutyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Dreifachbindung. Unless specifically stated, the 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. Alkyl radicals, also in the composite radicals such as alkoxy, haloalkyl etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl; 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.
Der Begriff„Alkenyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkenyl” also includes, in particular, straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1,3-Butadienyl und 1,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1,2-Propadienyl) und 1,2-Butadienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (C2-C4)-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- 1- propenyl, 2-Methyl-l-propenyl, l-Methyl-2-propenyl, 2-Methyl-2-propenyl. 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.
Der Begriff„Alkinyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkynyl” also includes, in particular, straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Hydrocarbon radicals with more than one triple bond or with one or more
Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1,3-Butatrienyl. (C2-C4)-Alkinyl bedeutet z.B. Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2-Butinyl, 3-Butinyl, 1- Methyl-2-propinyl . Der Begriff„Cycloalkyl“ bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-6 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, das (a) bevorzugt unsubstituiert, oder (b) durch Alkoxy, Cyano, Nitro, Alkylthio, Haloalkylthio, Halogen, Haloalkyl, Amino, Alkylamino, Bisalkylamino, Alkocycarbonyl, Hydroxycarbonyl, Arylalkoxycarbonyl, 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. The term “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 weiter substituiert ist. Im Falle von weiter substituiertem Cycloalkylen werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am Cy cloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfasst, wie beispielsweise Bicyclo[1.1.0]butan-l-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-l-yl, Bicyclo[l .1. l]pentan-l-yl, Bicyclo[2.1 0]pentan-2-yl, Bicyclo[2.1.0]pentan- 5-yl und Bicyclo[2.1.1]hexyl. Der Ausdruck "(C3-C6)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 6 Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. Aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl is further substituted. In the case of further substituted cycloalkylene, 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. In the case of optionally substituted cycloalkyl, 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. l] pentan-1-yl, bicyclo [2.1 0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl and bicyclo [2.1.1] hexyl. The expression “(C3-C6) -cycloalkyl” denotes a shorthand for cycloalkyl with three to 6 carbon atoms, corresponding to the range given for carbon atoms.
Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfasst, wie beispielsweise 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. In the case of substituted cycloalkyl, 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“ bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-6 C-Atomen, z.B. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, 1,3-Cyclohexadienyl oder 1,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. "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. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.
Der Begriff„Alkyliden“, z. B. auch in der Form (C1-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Alkyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H- Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B. =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 oder =C(C2H5)-C2H5. Cycloalkyliden bedeutet ein The term "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. Naturally, only positions on the base body at which two H atoms can be replaced by the double bond are possible as a binding site for alkylidene; Remnants are e.g. B. = CH 2 , = CH-CH 3 , = C (CH 3 ) -CH 3 , = C (CH 3 ) -C 2 H 5 or = C (C 2 H 5 ) -C 2 H 5. means cycloalkylidene a
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. carbocyclic radical that is linked via a double bond.
„Alkoxyalkyl“ steht für einen über eine Alkylgruppe gebundenen Alkoxyrest und„Alkoxyalkoxy“ bedeutet einen über ein Sauerstoffatom gebundenen Alkoxyalkylrest, z.B. (aber nicht beschränkt auf) Methoxymethoxy, Methoxyethoxy, Ethoxyethoxy, Methoxy-n-propyloxy. "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“ steht für einen über eine Alkylgruppe gebundenen Alkylthiorest und “Alkylthioalkyl” stands for an alkylthio radical bonded via an alkyl group and
„Alkylthioalkylthio“ bedeutet einen über ein Sauerstoffatom gebundenen Alkylthioalkylrest. ..Haloalkoxyalkyl steht für einen gebundenen Haloalkoxyrest und ..Haloalkylthioalkyl bedeutet einen über eine Alkylgruppe gebundenen Haloalkylthiorest. “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.
Erfmdungsgemäß steht "Haloalkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Halogenalkyl, vorzugsweise mit 1 bis 4 Kohlenstoffatomen, wie (C1-C4)-Haloalkylthio, z.B. (aber nicht beschränkt auf) Trifluormethylthio, Pentafluorethylthio, Difluormethyl, 2,2-Difluoreth-l-ylthio, 2,2,2-Difluoreth-l-ylthio, 3,3,3-prop-l-ylthio. According to the invention, "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.
Erfmdungsgemäß steht "Trialkylsilyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Si-Alkyl, vorzugsweise mit 1 bis 6 Kohlenstoffatomen, wie Tri-[ (C1- C2)-alkyl]silyl, z.B. (aber nicht beschränkt auf) Trimethylsilyl, Triethylsilyl. According to the invention, "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.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die allgemeine Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele If the compounds can form tautomers by hydrogen shift, which structurally formally would not be covered by the general formula (I), these tautomers are nonetheless 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. For example, many can
Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der Verbindung der allgemeinen Formel (I) umfasst werden. 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).
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von der allgmeinen Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der 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
Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfüng erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. 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. Likewise, 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.
Sofern die Verbindungen als Feststoffe erhalten werden, kann die Reinigung auch durch If the compounds are obtained as solids, the purification can also be done by
Umkristallisieren oder Digerieren erfolgen. Sofern einzelne Verbindungen (I) nicht auf den nachstehend beschriebenen Wegen zufriedenstellend zugänglich sind, können sie durch Derivatisierung anderer Verbindungen (I) hergestellt werden. Als Isolierungs-, Reinigungs- und Stereoisomerenauftrennungsverfahren von Verbindungen der allgemeinen Formel (I) kommen Methoden in Frage, die dem Fachmann aus analogen Fällen allgemein bekannt sind, z.B. durch physikalische Verfahren wie Kristallisation, Chromatographieverfahren, vor allem Säulenchromatographie und HPLC (Hochdruckflüssigchromatographie), Destillation, gegebenenfalls unter reduziertem Druck, Extraktion und andere Verfahren, können gegebenfalls verbleibende Gemische in der Regel durch chromatographische Trennung, z.B. an chiralen Festphasen, getrennt werden. Für präparative Mengen oder im industriellen Maßstab kommen Verfahren in Frage wie Kristallisation, z.B. diastereomerer Salze, die aus den Diastereomerengemischen mit optisch aktiven Säuren und gegebenenfalls bei vorhandenen sauren Gruppen mit optisch aktiven Basen erhalten werden können. Recrystallization or digestion take place. 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. For preparative quantities or on an industrial scale, 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.
Die vorliegende Erfindung beansprucht auch Verfahren zur Herstellung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I). The present invention also claims processes for the preparation of the compounds of the general formula (I) according to the invention.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können unter anderem ausgehend von bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren Bausteinen aus. Die Gruppierungen R1, R2, R3, R4 und R5 der allgemeinen Formel (I) haben in den nachfolgenden Schemata die zuvor definierten Bedeutungen, sofern nicht beispielhafte, aber nicht einschränkende, Definitionen erfolgen. 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.
Erfmdungsgemäße Verbindungen können beispielsweise nach der in Schema 1 angegebenen Methode hergestellt werden. Compounds according to the invention can be prepared, for example, by the method given in scheme 1.
Figure imgf000011_0001
Figure imgf000011_0001
Schema 1. Scheme 1.
Die Pyridinyloxypyridine der allgemeinen Formel (I) können über eine Substitution der Pyridine (E-I) in Gegenwart von Basen mit dem Hydroxypyridin (E-II), wobei LG eine Abgangsgruppe (wie zum Beispiel ein Halogen) ist, hergestellt werden (Schema 1). Die Base kann ein Carbonat-Salz von einem Alkali-Metall (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril, Dimethylformamid, oder 1 -Methyl -2 -pyrrolidon, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Wie für den Fachmann bekannt ist, können die Hydroxypyridine (E-II) auch als Pyridon- Tautomer vorliegen. 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. As is known to the person skilled in the art, the hydroxypyridines (E-II) can also be present as pyridone tautomers.
Pyridine der allgemeinen Formel (E-I) mit R1 = H sind literaturbekannt und können beispielsweise gemäß der in WO 2015/86519 und ähnlich beschriebenen Methoden hergestellt werden. Pyridines of the general formula (EI) with R 1 = H are known from the literature and can be prepared, for example, according to the methods described in WO 2015/86519 and similar.
Figure imgf000012_0001
Figure imgf000012_0001
Pyridine der allgemeinen Formel (E-I) mit R1 = Halogen können über eine Halogenierung der Pyridine (E-Ia) mit einem Halogenierungsreagenz hergestellt werden (Schema 2). Das Halogenierungsreagenz kann zum Beispiel N-Chlorsuccinimid, N-Bromsuccinimid oder N-Jodsuccinimid sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Pyridines of the general formula (EI) with R 1 = halogen can be prepared by halogenating the pyridines (E-Ia) with a halogenating reagent (scheme 2). 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.
Synthesebeispiel: Synthesis example:
Tabellenbeispiel Nr. 1-12: Table example no. 1-12:
Synthesestufe 1: 2,3-Dichlor-4-amino-5-nitropyridin:
Figure imgf000012_0002
Synthesis stage 1: 2,3-dichloro-4-amino-5-nitropyridine:
Figure imgf000012_0002
Eine Mischung von 3-Chlor-4-amino-5-nitropyridin (12.5 g, 72.0 mmol) und N-Chlorsuccinimid (11.5 g, 86.4 mmol) in Acetonitril (125 ml) wird bei 80 °C für 7 h erhitzt und anschließend auf A mixture of 3-chloro-4-amino-5-nitropyridine (12.5 g, 72.0 mmol) and N-chlorosuccinimide (11.5 g, 86.4 mmol) in acetonitrile (125 ml) is heated at 80 ° C. for 7 h and then on
Raumtemperatur abgekühlt und eingeengt. Durch anschließende säulenchromatographische Reinigung des resultierenden Rohproduktes konnte ein gelber Feststoff erhalten werden. Die Ausbeute beträgt 14.4 g (96% der Theorie). 1H NMR (400 MHz, CDCl3, d ppm): 8.99 (s, 1H), 8.10 (br s, 1H), 5.95 (br s, 1H). Cooled room temperature and concentrated. Subsequent purification of the resulting crude product by column chromatography made it possible to obtain a yellow solid. The yield is 14.4 g (96% of theory). 1 H NMR (400 MHz, CDCl 3 , d ppm): 8.99 (s, 1H), 8.10 (br s, 1H), 5.95 (br s, 1H).
Synthesestufe 2: 3-Fluor-2-[(5-chlor-2-pyridyl)oxy]-5-nitro-pyridin-4-amin (Tabellenbeispiel Nr. 1-12) Eine Mischung von 2,3-Dichlor-5-nitropyridin-4-amin (90 mg, 0.43 mmol), 5-Fluorpyridin-2-ol (54 mg, 0.48 mmol) und Cäsiumcarbonat (280 mg, 0.87 mmol) in Acetonitril (5 ml) wird bei 80 °C für 7 h erhitzt und anschließend auf Raumtemperatur abgekühlt, mit Wasser verdünnt und mit Essigester mehrmals extrahiert. Die vereinigten organischen Phasen werden über Natriumsulfat getrocknet, filtriert und eingeengt. Durch anschließende säulenchromatographische Reinigung des resultierenden 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
Rohproduktes konnte ein gelber Feststoff erhalten werden. Die Ausbeute beträgt 57 mg (43% der Theorie). A yellow solid could be obtained from the crude product. The yield is 57 mg (43% of theory).
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen erhält man die nachfolgend genannten und in Tabelle 1 dargestellten Verbindungen der allgemeinen Formel (I) In analogy to the preparation examples given above and recited at the appropriate point, the compounds of the general formula (I) mentioned below and shown in Table 1 are obtained
Figure imgf000013_0001
Figure imgf000013_0001
Tabelle 1 Table 1
Figure imgf000014_0001
Figure imgf000014_0001
NMR-Daten ausgewählter Beispiele NMR data of selected examples
Ausgewählte detaillierte Synthesebeispiele für die erfmdungsgemäßen Verbindungen der allgemeinen Formeln (I) sind im Folgenden aufgeführt. Die 1H-NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei 4H- NMR, Lösungsmittel CDC , oder d6-DMSO, interner Standard: Tetramethylsilan d = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, dq = Doppelquartett, dt = Doppeltriplett. Bei Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are listed below. The 1 H-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for 4 H-NMR, CDC solvent, or d 6 -DMSO, internal standard: tetramethylsilane d = 0.00 ppm), were obtained with a device from Bruker, and the signals indicated have the following meanings: br = broad (es); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of mixtures of diastereomers, either the significant signals of both diastereomers or the characteristic signal of the
Hauptdiastereomers angegeben. Main diastereomers indicated.
Die nachfolgend aufgeführten spektroskopischen Daten ausgewählter Tabellenbeispiele wurden über klassische 1H-N R-Interpretation ausgewertet. Klassische 1H-N R-Interpretation Beispiel Nr. 1-1 : The spectroscopic data of selected table examples listed below were evaluated using classic 1 HN R interpretation. Classic 1 HN R interpretation Example No. 1-1:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.97 (s, 1H), 7.68 (t, 1H), 7.05 (d, 1H), 6.88 (d, 1H), 6.34 (s, 1H), 2.51 (s, 3H). 1H-NMR (400 MHz, CDCI 3 d, ppm) 8.97 (s, 1H), 7.68 (t, 1H), 7.05 (d, 1H), 6.88 (d, 1H), 6.34 (s, 1H), 2.51 ( s, 3H).
Beispiel Nr. 1-2: Example no. 1-2:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.89 (s, 1H), 7.85 (d, 1H), 7.15 (dd, 1H), 6.35 (s, 1H), 3.89 (s, 3H). Beispiel Nr. 1-3: 1 H NMR (400 MHz, CDCI 3 d, ppm) 8.89 (s, 1H), 7.85 (d, 1H), 7.15 (dd, 1H), 6.35 (s, 1H), 3.89 (s, 3H). Example no. 1-3:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.86 (s, 1H), 7.71 (t, 1H), 7.08 (d, 1H), 6.90 (d, 1H), 2.51 (s, 3H). Beispiel Nr. 1-4: 1 H NMR (400 MHz, CDCI 3 d, ppm) 8.86 (s, 1H), 7.71 (t, 1H), 7.08 (d, 1H), 6.90 (d, 1H), 2.51 (s, 3H). Example no. 1-4:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.80 (s, 1H), 7.87 (d, 1H), 7.17 (dd, 1H), 3.90 (s, 3H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.80 (s, 1H), 7.87 (d, 1H), 7.17 (dd, 1H), 3.90 (s, 3H).
Beispiel Nr. 1-5: Example no. 1-5:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.91 (s, 1H), 8.34-8.32 (m, 1H), 7.85-7.81 (m, 1H), 7.22-7.19 (m, 1H), 7.14-7.12 (m, 1H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.91 (s, 1H), 8.34-8.32 (m, 1H), 7.85-7.81 (m, 1H), 7.22-7.19 (m, 1H), 7.14-7.12 (m, 1H).
Beispiel Nr. 1-6: Example no. 1-6:
1H-NMR (400 MHz, CDC d, ppm) 8.83 (s, 1H), 8.17 (dd, 1H), 7.61-7.56 (m, 1H), 7.30-7.26 (m, 1H). Beispiel Nr. 1-7: 1 H-NMR (400 MHz, CDC d, ppm) 8.83 (s, 1H), 8.17 (dd, 1H), 7.61-7.56 (m, 1H), 7.30-7.26 (m, 1H). Example no. 1-7:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.82 (s, 1H), 7.94 (dd, 1H), 7.33 (dd, 1H), 7.24 (dd, 1H), 3.85 (s, 3H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.82 (s, 1H), 7.94 (dd, 1H), 7.33 (dd, 1H), 7.24 (dd, 1H), 3.85 (s, 3H).
Beispiel Nr. 1-8: Example no. 1-8:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.90 (s, 1H), 8.15 (d, 1H), 7.65 (d, 1H), 7.13 (dd, 1H), 2.30 (s, 3H). Beispiel Nr. 1-9: 1 H NMR (400 MHz, CDCI 3 d, ppm) 8.90 (s, 1H), 8.15 (d, 1H), 7.65 (d, 1H), 7.13 (dd, 1H), 2.30 (s, 3H). Example no. 1-9:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.86 (s, 1H), 7.98 (s, 1H), 7.46 (s, 1H), 2.32 (s, 3H), 2.23 (s, 3H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.86 (s, 1H), 7.98 (s, 1H), 7.46 (s, 1H), 2.32 (s, 3H), 2.23 (s, 3H).
Beispiel Nr. 1-10: Example no. 1-10:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.88 (s, 1H), 8.16 (s, 1H), 7.64 (d, 1H), 7.03 (d, 1H), 2.35 (s, 3H). Beispiel Nr. 1-11 : 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.88 (s, 1H), 8.16 (s, 1H), 7.64 (d, 1H), 7.03 (d, 1H), 2.35 (s, 3H). Example No. 1-11:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.89 (s, 1H), 8.27 (d, 1H), 7.79 (dd, 1H), 7.10 (dd, 1H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.89 (s, 1H), 8.27 (d, 1H), 7.79 (dd, 1H), 7.10 (dd, 1H).
Beispiel Nr. 1-12: Example no. 1-12:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.87 (s, 1H), 8.18 (d, 1H), 7.58-7.54 (m, 1H), 7.12 (dd, 1H). Beispiel Nr. 1-13: 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.87 (s, 1H), 8.18 (d, 1H), 7.58-7.54 (m, 1H), 7.12 (dd, 1H). Example no. 1-13:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.89 (s, 1H), 8.36 (d, 1H), 7.92 (dd, 1H), 7.05 (d, 1H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.89 (s, 1H), 8.36 (d, 1H), 7.92 (dd, 1H), 7.05 (d, 1H).
Beispiel Nr. 1-14: Example no. 1-14:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.94 (s, 1H), 8.54 (d, 1H), 8.05 (dd, 1H), 7.25 (d, 1H). 1 H NMR (400 MHz, CDCI 3 d, ppm) 8.94 (s, 1H), 8.54 (d, 1H), 8.05 (dd, 1H), 7.25 (d, 1H).
Beispiel Nr. 1-15: Example No. 1-15:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.89 (s, 1H), 8.34 (s, 1H), 7.03 (s, 1H), 2.45 (s, 3H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.89 (s, 1H), 8.34 (s, 1H), 7.03 (s, 1H), 2.45 (s, 3H).
Beispiel Nr. 1-16: Example no. 1-16:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.92 (s, 1H), 8.21 (d, 1H), 7.21 (dd, 1H), 7.17 (d, 1H). 1 H NMR (400 MHz, CDCI 3 d, ppm) 8.92 (s, 1H), 8.21 (d, 1H), 7.21 (dd, 1H), 7.17 (d, 1H).
Beispiel Nr. 1-17: Example no. 1-17:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.91 (s, 1H), 8.18 (d, 1H), 7.03 (d, 1H), 6.95 (s, 1H), 2.42 (s, 3H). Beispiel Nr. 1-18: 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.91 (s, 1H), 8.18 (d, 1H), 7.03 (d, 1H), 6.95 (s, 1H), 2.42 (s, 3H). Example no. 1-18:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.85 (s, 1H), 8.19 (d, 1H), 7.87 (d, 1H). 1 H-NMR (400 MHz, CDCI 3 d, ppm) 8.85 (s, 1H), 8.19 (d, 1H), 7.87 (d, 1H).
Beispiel Nr. 1-19: Example No. 1-19:
1H-NMR (400 MHz, CDCI3 d, ppm) 8.84 (s, 1H), 7.87 (d, 1H), 7.01 (d, 1H), 2.48 (s, 3H). 1 H NMR (400 MHz, CDCI 3 d, ppm) 8.84 (s, 1H), 7.87 (d, 1H), 7.01 (d, 1H), 2.48 (s, 3H).
Gegenstand der vorliegenden Erfindung ist weiterhin die Verwendung einer oder mehrerer The present invention also relates to the use of one or more
Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-1) bis (1-19) und/oder deren Salze, jeweils wie oben definiert, als Herbizid und/oder Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen. 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 (1-19) and / or their salts, in each case as defined above, as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.
Gegenstand der vorliegenden Erfindung ist ferner ein Verfahren zur Bekämpfung von Schadpflanzen und/oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-1) bis (1-19) und/oder deren Salze, jeweils wie oben definiert, oder eines erfmdungsgemäßen Mittels, wie nachstehend definiert, 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,
auf die (Schad)Pflanzen, (Schad)Pflanzensamen, den Boden, in dem oder auf dem die on the (harmful) plants, (harmful) plant seeds, the soil in which or on which the
(Schad)Pflanzen wachsen, oder die Anbaufläche appliziert wird. (Harmful) plants grow, or the cultivation area is applied.
Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen, vorzugsweise in Nutzpflanzenkulturen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-1) bis (1-19) und/oder deren Salze, jeweils wie oben definiert, oder eines erfmdungsgemäßen Mittels, wie nachstehend definiert, 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,
auf unerwünschte Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut der unerwünschten Pflanzen (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die unerwünschte Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die unerwünschte Pflanzen wachsen werden) appliziert wird. 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. 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) or the cultivated area (ie area on which the unwanted plants will grow) is applied.
Gegenstand der vorliegenden Erfindung ist ferner auch ein Verfahren zur Bekämpfung zur The present invention also provides a method of combating
Wachstumsregulierung von Pflanzen, vorzugsweise von Nutzpflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-1) bis (1-19) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, Growth regulation of plants, preferably of useful plants, characterized in that an effective amount 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 (1-19 ) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below,
die Pflanze, das Saatgut der Pflanze (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die Pflanzen wachsen werden) appliziert wird. 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 soil of cultivated land or non-cultivated land) or the cultivation area (ie area on which the plants will grow) is applied.
Dabei können die erfmdungsgemäßen Verbindungen bzw. die erfmdungsgemäßen Mittel z.B. im Vorsaat- (gegebenenfalls auch durch Einarbeitung in den Boden), Vorauflauf- und/oder 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
NachauflaufVerfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfmdungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Post-emergence method can be applied. Some representatives of the monocotyledonous and dicotyledonous weed flora, which can be used to control the compounds according to the invention, without the mentioning of them being intended to restrict to certain species, may be mentioned as examples.
Vorzugsweise werden in einem erfmdungsgemäßen Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung in Kulturen von Nutzpflanzen oder Zierpflanzen eingesetzt, wobei die Nutzpflanzen oder Zierpflanzen in einer bevorzugten Ausgestaltung transgene Pflanzen sind. In a method according to the invention for controlling harmful plants or for regulating the growth of plants, 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.
Die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze eignen sich zur Bekämpfung der folgenden Gattungen von monokotylen und dikotylen Schadpflanzen: 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:
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. 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.
Dikotyle Schadpflanzen der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicots harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia , Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Werden die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) vor dem Keimen der Schadpflanzen (Ungräser und/oder Unkräuter) auf die Erdoberfläche appliziert (VorauflaufVerfahren), so wird entweder das Auflaufen der Ungras- bzw. Unkrautkeimlinge vollständig verhindert oder diese wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. If 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.
Bei Applikation der erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) auf die grünen Pflanzenteile im NachauflaufVerfahren tritt nach der Behandlung Wachstumsstop ein und die When the compounds of the general formula (I) according to the invention are applied to the green parts of the plant in the post-emergence process, after the treatment, growth stops and the
Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. 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.
Obgleich die erfmdungsgemäßen Verbindungen der allgemeinnen Formel (I) eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Uactuca, Einum, Although 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,
Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, abhängig von der Struktur der jeweiligen erfmdungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledon cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound according to the invention and their application rate only insignificantly or not at all damaged. 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.
Darüberhinaus weisen die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende In addition, the compounds of the general formula (I) according to the invention have excellent properties (depending on their particular structure and the application rate applied)
wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von growth-regulatory properties in cultivated plants. They intervene in the plant's own metabolism in a regulating manner and are therefore able to specifically influence
Pflanzeninhaltsstoffen und zur Emteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe der allgemeinen Formel (I) auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe.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.
So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Thus, 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.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. With regard to 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.
Vorzugsweise können die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) auch als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. 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.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Because of their herbicidal and plant growth regulatory properties, 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
Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, 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,
Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z.B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung liegen. Composition and special ingredients. Thus, 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.
Bevorzugt ist die Anwendung der erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Triticale, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Preference is given to using the compounds of the general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example of Grains such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
Vorzugsweise können die Verbindungen der allgemeinen Formel (I) als Herbizide in The compounds of the general formula (I) can preferably be used as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Crops of useful plants are used which are resistant to the phytotoxic effects of herbicides or which have been made resistant by genetic engineering.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Conventional ways of producing new plants that have modified properties compared to previously occurring plants exist, for example, in classic ways
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden. Breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be produced using genetic engineering.
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind dem Fachmann bekannt. Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z.B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art. For such genetic manipulations, 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
untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden. adapters or linkers can be attached to the fragments.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann The production of plant cells with reduced activity of a gene product can
beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. 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.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA- Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. For this purpose, on the one hand, 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.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z.B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any desired compartment of the plant cell. In order to achieve the localization in a certain compartment, for example, the coding region can be linked to DNA sequences which ensure the localization in a certain compartment. Such 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.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be any plant
Pflanzenspezies handeln, d.h. sowohl monokotyle als auch dikotyle Pflanzen. Act plant species, i.e. both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Thus, transgenic plants can be obtained which have altered properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or the expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z.B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z.B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. 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.
Bei der Anwendung der erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. When 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.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze als Herbizide zur Bekämpfung von Schadpflanzen in Kulturen von Nutz- oder Zierpflanzen, gegebenenfalls in transgenen Kulturpflanzen. 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.
Bevorzugt ist die Verwendung von Verbindungen der allgemeinen Formel (I) in Getreide, dabei vorzugsweise Mais, Weizen, Gerste, Roggen, Hafer, Hirse, oder Reis, im Vor- oder Nachauflauf. Preference is given to using compounds of the general formula (I) in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, pre- or post-emergence.
Bevorzugt ist auch die Verwendung von Verbindungen der allgemeinene Formel (I) in Soja im Vor- oder Nachauflauf. Die Verwendung erfmdungsgemäßer Verbindungen der Formel (I) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem einer Verbindung der allgemeinen Formel (I) oder deren Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird. 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").
Gegenstand der Erfindung ist auch die Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salzen bzw. eines erfmdungsgemäßen Mittels (wie nachstehend definiert) (in einem Verfahren) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehreren Verbindungen der allgemeinen Formel (I) oder deren Salzen auf die Pflanzen (Schadpflanzen, gegebenenfalls zusammen mit den Nutzpflanzen) Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert. 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.
Gegenstand der Erfindung ist auch ein herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel The invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
(a) eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthält wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten (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
Ausgestaltung, insbesondere eine oder mehrere Verbindungen der Formeln Design, in particular one or more compounds of the formulas
(1-1) bis (1-19) und/oder deren Salze, jeweils wie oben definiert, (1-1) to (1-19) and / or their salts, each as defined above,
und and
(b) ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii): (b) one or more other substances selected from groups (i) and / or (ii):
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden (d.h. solche, die nicht der oben definierten allgemeinen Formel (I) entsprechen), Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (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 other growth regulators,
(ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. (ii) one or more formulation auxiliaries customary in crop protection.
Die weiteren agrochemischen wirksamen Stoffe des Bestandteils (i) eines erfmdungsgemäßen Mittels sind dabei vorzugsweise ausgewählt aus der Gruppe der Stoffe, die in "The Pesticide Manual", 16th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 genannt sind. The further agrochemically active substances of 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.
Ein erfindungsgemäßes herbizides oder pflanzenwachstumsregulierendes Mittel, umfasst vorzugsweise ein, zwei, drei oder mehr im Pflanzenschutz übliche Formulierungshilfsmittel (ii) ausgewählt aus der Gruppe bestehend aus Tensiden, Emulgatoren, Dispergiermitteln, Filmbildnem, Verdickungsmitteln, anorganischen Salzen, Stäubemitteln, bei 25 °C und 1013 mbar festen Trägerstoffen, vorzugsweise adsorptionsfähigen, granulierten Inertmaterialien, Netzmitteln, Antioxidationsmitteln, Stabilisatoren, Puffersubstanzen, Antischaummitteln, Wasser, organischen Lösungsmitteln, vorzugsweise bei 25 °C und 1013 mbar mit Wasser in jedem beliebigen Verhältnis mischbare organische Lösungsmittel. 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.
Die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) können in Form von Spritzpulvem, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, die Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthalten. 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.
Die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: 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:
Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, 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), dispersions oil- or water-based, oil-miscible solutions,
Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Capsule suspensions (CS), dusts (DP), dressings, granulates for the litter and
Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Floor application, granules (GR) in the form of micro, spray, lift and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
Mikrokapseln und Wachse. Microcapsules and waxes.
Diese einzelnen Formulierungstypen und die Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind dem Fachmann bekannt, und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvente Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Ine., N.Y. 1964; Schönfeldt, "Grenzflächenaktive These individual formulation types and the formulation auxiliaries such as inert materials, surfactants, solvents and other additives are known to the person skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvent Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents," Chem. Publ. Co. Ine., N.Y. 1964; Schönfeldt, "Interface Active
Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler," Chemische Technologie ", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, 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,
Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. 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. To produce the wettable powders, 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.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calcium-Salze wie 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). Examples of emulsifiers that can be used are: alkylarylsulfonic acid calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder 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
Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene sorbitan fatty acid ester.
Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. 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.
Emulsionen, z.B. Öl-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Emulsions, e.g. Oil-in-water emulsions (EW), for example by means of stirrers,
Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Colloid mills and / or static mixers using aqueous organic
Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hersteilen. Solvents and optionally surfactants, such as are e.g. are already listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete 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
Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischem und Extrusion ohne festes Inertmaterial hergestellt. 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.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulaten siehe z.B. Verfahren in "Spray- Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. For the production of plate, fluidized bed, extruder and spray granules, see e.g. Method in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Ine., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. For further details on the formulation of plant protection products see e.g. G.C. Klingman, "Weed Control as a Science," John Wiley and Sons, Ine., New York, 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Die agrochemischen Zubereitungen, vorzugsweise herbizide oder pflanzenwachstumsregulierende Mittel der vorliegenden Erfindung enthalten vorzugsweise eine Gesamtmenge von 0,1 bis 99 Gew.-%, bevorzugt 0,5 bis 95 Gew.-%, weiter bevorzugt 1 bis 90 Gew.-%, insbesondere bevorzugt 2 bis 80 Gew.-%, an Wirkstoffen der allgemeinen Formel (I) und deren Salzen. 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.
In Spritzpulvem beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige In wettable powder, 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
Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten hegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. 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. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Beispiele für Formulierungshilfsmittel sind unter anderem in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998) beschrieben. Die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder Wachstumsregulatoren kombiniert eingesetzt werden, z.B. als Fertigformulierung oder als In addition, 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. Examples of 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
Tankmischungen. Die Kombinationsformulierungen können dabei auf Basis der obengenannten Formulierungen hergestellt werden, wobei die physikalischen Eigenschaften und Stabilitäten der zu kombinierenden Wirkstoffe zu berücksichtigen sind. 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.
Als Kombinationspartner für die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat- Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. in Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 und der dort zitierten Literatur beschrieben sind. 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.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen The selective control of harmful plants in crops of useful and ornamental plants is of particular interest. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many crops, phytotoxicities can in principle occur on the crop plants in some crops and especially in the case of mixtures with other herbicides which are less selective. In this regard are combinations
erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen der allgemeinen Formel (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und inventive compounds (I) of particular interest which the compounds of general formula (I) or their combinations with other herbicides or pesticides and
Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. 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.
Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der The weight ratio of herbicide (mixture) to safener generally depends on the
Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200: 1 bis 1:200, vorzugsweise 100: 1 bis 1: 100, insbesondere 20: 1 bis 1 :20. Die Safener können analog den Verbindungen der allgemeinen Formel (I) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als The application rate of the herbicide 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 mixtures thereof with other herbicides / pesticides and as
Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden. Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid-Safener- Formulierungen gegebenenfalls in üblicherweise verdünnt z.B. bei Spritzpulvem, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Ready-made formulation or tank mix with the herbicides can be provided and applied. For use, 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.
Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der allgemeinen Formel (I) und/oder deren Salze. Die External conditions such as temperature, humidity etc. influence to a certain extent the application rate of the compounds of the general formula (I) and / or their salts. The
Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der allgemeinen Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. The application rate can vary within wide limits. For use as a herbicide for combating harmful plants, 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.
Bei der Anwendung von erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salzen als Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Gesamt- Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im When using compounds of the general formula (I) according to the invention and / or salts thereof as plant growth regulators, for example as stalk shorteners in crop plants, as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or maize , 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
Vorauflauf oder im Nachauflauf. Pre-emergence or post-emergence.
Die Applikation als Halmverkürzer kann in verschiedenen Stadien des Wachstums der Pflanzen erfolgen. Bevorzugt ist beispielsweise die Anwendung nach der Bestockung am Beginn des 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
Längenwachstums . Growth in length.
Alternativ kommt bei der Anwendung als Pflanzenwachstumsregulator auch die Behandlung des Saatguts in Frage, welche die unterschiedlichen Saatgutbeiz- und Beschichtungstechniken einschließt. Die Aufwandmenge hängt dabei von den einzelnen Techniken ab und kann in Vorversuchen ermittelt werden. Alternatively, when used as a plant growth regulator, 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.
Als Kombinationspartner für die erfmdungsgemäßen Verbindungen der allgemeinen Formel (I) in erfmdungsgemäßen Mitteln (z.B. Mischungsformuberungen oder im Tank-Mix) sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p- Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II oder Combination partners for the compounds of the general formula (I) according to the invention in agents according to the invention (for example mixture formulations or in the tank mix) 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 beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 16th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 und dort zitierter Literatur beschrieben sind. Nachfolgend werden beispielhaft bekannte Herbizide oder Pflanzenwachstumsregulatoren genannt, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, wobei diese Wirkstoffe entweder mit ihrem "common name" in der englischsprachigen Variante gemäß International Organization for Standardization (ISO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche 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. Everyone is always there
Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische Isomere umfaßt, auch wenn diese nicht explizit erwähnt sind. Use forms such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned.
Beispiele für solche herbiziden Mischungspartner sind: Examples of such herbicidal mixing 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, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfüresate, bensulfüron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac- sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfüron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofümesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfüron, etobenzanid, F-9600, F-5231, i.e. N-[2- Chlor-4-fluor-5 -[4-(3 -fluorpropyl)-4,5 -dihydro-5 -oxo- 1 H-tetrazol- 1 -yl] -phenyl] -ethansulfonamid, F - 7967, i.e. 3-[7 -Chlor-5 -fluor-2-(trifluormethyl)- lH-benzimidazol-4-yl] - 1 -methyl-6- (trifluormethyl)pyrimidin-2,4(1H,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, 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, azimsulfuron, ben-sulphuronate, benazolin, benflubutamidate , bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, potassium, bromoxynilate and -butyrate busoxinone, butachlor, butafenacil, butamifos, butenachlor, butraline, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, ch lorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorosulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodyllop, clodyrlop, clodyrlop-propaz cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine , -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium , daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl-1,2-oxazolidine-3 - one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-l, 2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromoc, diuronithiopoc, diquat-dibromoc esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofümesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfüron, etobenzanid, F-9600, F-5231, ie N- [2- chloro-4-fluoro-5 - [4- ( 3-fluoropropyl) -4,5-dihydro-5-oxo-1 H-tetrazol-1 -yl] -phenyl] -ethanesulfonamide, F-7967, ie 3- [7 -chloro-5-fluoro-2- (trifluoromethyl ) - lH-benzimidazol-4-yl] - 1 -methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl,
flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfüron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. 0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-l- methyl-3-(trifluonnethyl)-lH-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, 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, flupyrsulfüron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate-, glufosinuf-ammonate, glufosinate-sodium P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium and -trimesium, H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl- isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, ie l- (Dimethoxyphosphoryl) -ethyl- (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazethapyrium, imazaquin- ammonium -immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, ieH 3 - ({[5- (difluoromethyl) -l-methyl-3- (trifluonnethyl) -lH-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1,2- oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium , and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione,
methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l -methyl - 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulffron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5 -[2-chlor-4-(trifluormethyl)phenoxy] -2-nitrobenzoat, SYP-300, i.e. 1 -[7 -Fluor-3 -oxo-4-(prop-2-in- 1 - yl)-3 ,4-dihydro-2H- 1 ,4-benzoxazin-6-yl] -3 -propyl-2-thioxoimidazolidin-4,5 -dion, 2,3 ,6-TB A, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea Sulfate, vemolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: methabenzthiazuron, 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, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, petroleum, pentachloramid, pethentoxazone, petroleum, pentoxsulamid, pethentoxazone, petroleum, pethentoxazone, petroleum, pentoxazone, petroleum, pentoxsulamid phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone, lfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulffron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulphan, pyrithiobac, pyrithiobaclamulac, pyrithiobaclamulac, quyroxasulphone, quizofinclac, quyroxasulphone, quyroxasulphone, quizofinclac, quyroxasulphone, quyroxasulphone, pyroxasulphone quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfosulfuron, SYSulfuron.-methyl -523, SYP-249, ie 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5 - [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300 , ie 1 - [7 -fluoro-3-oxo-4- (prop-2-in-1-yl) -3, 4-dihydro-2H-1, 4-benzoxazin-6-yl] -3 -propyl- 2-thioxoimidazolidine-4,5-dione, 2,3, 6-TB A, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenchlor, thiazopyl, thiencarbazone, thiencarbazone-methyl , thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricobin-sulfuron, triflusulfuron, triflusulfurazine, triflusulfur, triflusulfur, triflusulfazine, triflusulfuron, triflusulfur, triflusulfur, triflusulfazine, triflusulfural, triflusulfur, triflusulfural -methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, ie 3,4-dichloro-N- {2- [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, as well as the following connections:
Figure imgf000031_0001
Figure imgf000031_0001
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Examples of plant growth regulators as possible mixing partners are:
Acibenzolar, acibenzolar-S-methyl, 5-Aminolävulinsäure, ancymidol, 6-benzylaminopurine, Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
Brassinolid, Catechin, chlormequat Chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und 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, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat Chloride, 1-methylcyclopropene, 2-(l-naphthyl)acetamide, 1-naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone,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) acetamide, 1-naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone,
Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. Salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
Ebenfalls als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) kommen beispielsweise die folgenden Safener in Frage: The following safeners are also suitable as combination partners for the compounds of the general formula (I) according to the invention:
51) Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate: 51) Compounds from the group of heterocyclic carboxylic acid derivatives:
S1a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1a), vorzugsweise S1 a ) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1 a ), preferably
Verbindungen wie Connections like
l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3 -carbonsäure, 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S 1-1) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; Ethyl l- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (S 1-1) ("Mefenpyr-diethyl"), and related compounds, as described in WO -A-91/07874;
S1b) Derivate der Dichlorphenylpyrazolcarbonsäure (S lb), vorzugsweise Verbindungen wie S1 b ) derivatives of dichlorophenylpyrazole carboxylic acid (S l b ), preferably compounds such as
1 -(2,4-Dichlorphenyl)-5-methylpyrazol-3 -carbonsäureethylester (S 1 -2), 1 - (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylic acid ethyl ester (S 1 -2),
l-(2,4-Dichlorphenyl)-5-isopropylpyrazol-3-carbonsäureethylester (S 1-3), ethyl l- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (S 1-3),
1 -(2,4-Dichlorphenyl)-5 -( 1 , 1 -dimethyl-ethyl)pyrazol-3 -carbonsäureethylester (S 1 -4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind; 1 - (2,4-dichlorophenyl) -5 - (1,1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S 1 -4) and related compounds, as they are in EP-A-333131 and EP-A-269806 are described;
S1c) Derivate der 1, 5 -Diphenylpyrazol-3 -carbonsäure (S1c), vorzugsweise Verbindungen wie S1 c ) derivatives of 1, 5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as
l-(2,4-Dichlorphenyl)-5-phenylpyrazol-3 -carbonsäureethylester (S 1-5), ethyl l- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S 1-5),
l-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (S 1-6) und verwandte Methyl l- (2-chlorophenyl) -5-phenylpyrazole-3-carboxylate (S 1-6) and related
Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; Compounds as described, for example, in EP-A-268554;
S1d) Verbindungen vom Typ der Triazolcarbonsäuren (S1d), vorzugsweise Verbindungen wie S1 d ) compounds of the triazole carboxylic acid type (S1 d ), preferably compounds such as
Fenchlorazol(-ethylester), d.h. l-(2,4-Dichlorphenyl)-5-trichlormethyl-(lH)-l,2,4-triazol-3- carbonsäureethylester (Sl-7), und verwandte Verbindungen, wie sie in EP-A-174562 und EP-A-346620 beschrieben sind; Fenchlorazole (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;
S1e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure(S1e), vorzugsweise Verbindungen wie 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
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S 1-8) oder 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (S 1-8) or
5 -Phenyl -2-isoxazolin-3 -carbonsäureethylester (S1-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-carbonsäure (Sl-10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester (S1-11) ("Isoxadifen-ethyl") 5-phenyl -2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10 ) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) ("isoxadifen-ethyl")
oder -n-propylester (S1-12) oder 5 -(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3 -carbon- säureethylester (S1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind. or -n-propyl ester (S1-12) or 5 - (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13), as described in patent application WO-A-95/07897 are described.
S2) Verbindungen aus der Gruppe der 8-Chinolinoxyderivate (S2): S2) Compounds from the group of the 8-quinolineoxy derivatives (S2):
S2a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise S2 a ) compounds of the 8-quinolineoxyacetic acid type (S2 a ), preferably
(5-Chlor-8-chinolinoxy)essigsäure-(l-methylhexyl)-ester ("Cloquintocet-mexyl") (S2-1), (5-Chlor-8-chinolinoxy)essigsäure-(1,3-dimethyl-but-l-yl)-ester (S2-2), (5-chloro-8-quinolinoxy) acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-l-yl) ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester (S2-3), (5-chloro-8-quinolinoxy) acetic acid-4-allyl-oxy-butyl ester (S2-3),
(5-Chlor-8-chinolinoxy)essigsäure-l-allyloxy-prop-2-ylester (S2-4), (5-chloro-8-quinolinoxy) acetic acid-l-allyloxy-prop-2-yl ester (S2-4),
(5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5), (5-chloro-8-quinolinoxy) acetic acid ethyl ester (S2-5),
(5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S2-6),
(5-Chlor-8-chinobnoxy)essigsäureallylester (S2-7), (5-chloro-8-quinobnoxy) acetic acid allyl ester (S2-7),
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-1-ethylester (S2-8), (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -1-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-l-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind; (5-Chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366 are described, and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum , Iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34048;
S2b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise S2 b ) compounds of the (5-chloro-8-quinolinoxy) malonic acid type (S2 b ), preferably
Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, Compounds such as (5-chloro-8-quinolinoxy) malonic acid diethyl ester,
(5-Chlor-8-chinolinoxy)malonsäurediallylester, (5-chloro-8-quinolinoxy) malonic acid diallyl ester,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind. (5-chloro-8-quinolinoxy) malonic acid methyl-ethyl ester and related compounds, as described in EP-A-0 582 198.
S3) Wirkstoffe vom Typ der Dichloracetamide (S3), die häufig als Vorauflaufsafener S3) Active ingredients of the dichloroacetamide type (S3), which are often used as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z. B. (soil effective safeners) are used, such as. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1), "Dichlormid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-l,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,-dimethyl-l,3-oxazobdin) der Firma Stauffer (S3-3), "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-Dichloracetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin) (S3-4), "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]-dichloracetamid) der Firma PPG "PPG-1292" (N-Allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide) from PPG
Industries (S3-5), Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6), "DKA-24" (N-Allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-l-oxa-3-aza-spiro[4,5]decan) der Firma "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro [4.5] decane) from the company
Nitrokemia bzw. Monsanto (S3-7), Nitrokemia or Monsanto (S3-7),
"TI-35" (1-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8), "TI-35" (1-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9) "Diclonon" (Dicyclonon) or "BAS145138" or "LAB145138" (S3-9)
((RS)-1-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazobdin) (S3-10), sowie dessen (R)-Isomer (S3-11). ((RS) -1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "Furilazol" or "MON 13900" ((RS) -3-dichloroacetyl- 5- (2-furyl) -2,2-dimethyloxazobdin) (S3-10), and its (R) -isomer (S3-11).
S4) Verbindungen aus der Klasse der Acylsulfonamide (S4): S4a) N-Acylsulfonamide der Formel (S4a) und deren Salze wie sie in der WO-A-97/45016 beschrieben sind,
Figure imgf000034_0001
S4) Compounds from the class of the acylsulfonamides (S4): S4 a ) N-acylsulfonamides of the formula (S4 a ) and their salts as described in WO-A-97/45016,
Figure imgf000034_0001
worin wherein
RA 1 (C1-C6)Alkyl, (C3-C6)Cycloalkyl. wobei die 2 letztgenannten Reste durch VA R A 1 (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl. the latter two residues being replaced by VA
Substituenten aus der Gruppe Halogen, (C1-C4)Alkoxy, (C1-C6)Haloalkoxy und (C1- C4)Alkylthio und im Falle cyclischer Reste auch durch (C1-C4)Alkyl und (C1-C4)Haloalkyl substituiert sind; Substituents from the group halogen, (C 1 -C 4) alkoxy, (C 1 -C 6) haloalkoxy and (C 1 - C 4) alkylthio and in case of cyclic radicals, also by (C 1 -C 4) alkyl and (C 1 -C 4 ) haloalkyl are substituted;
RA 2 Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3; R A 2 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
mA 1 oder 2; m A 1 or 2;
VA ist 0, 1, 2 oder 3 bedeuten; V A is 0, 1, 2 or 3;
S4b) Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze, wie sie in der WO-A-99/16744 beschrieben sind, S4 b ) compounds of the 4- (benzoylsulfamoyl) benzamide type of the formula (S4 b ) and their salts, as described in WO-A-99/16744,
Figure imgf000034_0002
Figure imgf000034_0002
worin wherein
RB 1 , RB 2 unabhängig voneinander Wasserstoff, (C1-C6) Alky l (C3-C6)Cycloalkyl, (C3-R B 1 , R B 2 independently of one another hydrogen, (C 1 -C 6 ) alkyl (C 3 -C 6 ) cycloalkyl, (C 3 -
C6)Alkenyl, (C3-C6)Alkinyl, C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
RB 3 Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl oder (C1-C4)Alkoxy und R B 3 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkoxy and
mB 1 oder 2 bedeuten, m B mean 1 or 2,
z.B. solche worin e.g. such in what
RB 1 = Cyclopropyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist ("Cyprosulfamide", S4-1),R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe ("Cyprosulfamide", S4-1),
RB 1 = Cyclopropyl, RB 2 = Wasserstoff und (RB 3) = 5-Cl-2-OMe ist (S4-2), R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-2),
RB 1 = Ethyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist (S4-3), R B 1 = ethyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe is (S4-3),
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB 3) = 5-Cl-2-OMe ist (S4-4) und R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-4) and
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist (S4-5); R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe (S4-5);
S4c) Verbindungen aus der Klasse der Benzoylsulfamoylphenylhamstoffe der Formel (S4c), wie sie in der EP-A-365484 beschrieben sind, S4 c ) compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4 c ), as described in EP-A-365484,
Figure imgf000034_0003
worin
Figure imgf000034_0003
wherein
RC 1, RC 2 unabhängig voneinander Wasserstoff, (C1-C8)Alkyl, (C3-C8)Cycloalkyl, (C3-R C 1 , R C 2 independently of one another hydrogen, (C 1 -C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -
C6)Alkenyl, (C3-C6)Alkinyl, C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
RC 3 Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3 und R C 3 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 and
mc 1 oder 2 bedeuten; mc is 1 or 2;
beispielsweise for example
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylhamstoff, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylhamstoff, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
l-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylhamstoff; 1- [4- (N-4,5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea;
S4d) Verbindungen vom Typ der N-Phenylsulfonylterephthalamide der Formel (S4d) und deren Salze, die z.B. bekannt sind aus CN 101838227, S4 d ) compounds of the N-phenylsulfonyl terephthalamide type of the formula (S4 d ) and their salts, which are known, for example, from CN 101838227,
Figure imgf000035_0001
Figure imgf000035_0001
worin wherein
RD 4 Halogen, (C1-C4)Alkyl, (C1-C4)Alkoxy, CF3; R D 4 halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
mD 1 oder 2; m D 1 or 2;
RD 5 Wasserstoff, (C1-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5-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 -
C6)Cycloalkenyl bedeutet. C 6 ) is cycloalkenyl.
S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen S5) Active ingredients from the class of hydroxyaromatics and the aromatic-aliphatic
Carbonsäurederivate (S5), z.B. Carboxylic acid derivatives (S5), e.g.
3 ,4,5 -Triacetoxybenzoesäureethylester, 3 ,5 -Dimethoxy-4-hydroxybenzoesäure, 3,5- Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4- Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO-A- 2005/016001 beschrieben sind. 3, 4,5-Triacetoxybenzoic acid ethyl ester, 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) Wirkstoffe aus der Klasse der l,2-Dihydrochinoxalin-2-one (S6), z.B. S6) Active ingredients from the class of the 1,2-dihydroquinoxalin-2-ones (S6), e.g.
1 -Methyl-3 -(2-thienyl)- 1 ,2-dihydrochinoxalin-2-on, 1 -Methyl-3 -(2-thienyl)- 1 ,2-dihydro- chinoxalin-2-thion, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on-hydrochlorid, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on, wie sie in der WO- A-2005/112630 beschrieben sind. 1 -Methyl-3 - (2-thienyl) -1, 2-dihydroquinoxalin-2-one, 1 -methyl-3 - (2-thienyl) -1, 2-dihydroquinoxalin-2-thione, 1- (2 -Aminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin-2-one hydrochloride, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin- 2-one, as described in WO-A-2005/112630.
S7) Verbindungen aus der Klasse der Diphenylmethoxyessigsäurederivate (S7), z.B. S7) compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g.
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1), Diphenylmethoxyacetic acid methyl ester (CAS Reg.Nr. 41858-19-9) (S7-1),
Diphenylmethoxyessigsäureethylester oder Diphenylmethoxyessigsäure wie sie in der WO-A- 98/38856 beschrieben sind. Ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid as described in WO-A-98/38856.
S8) Verbindungen der Formel (S8), wie sie in der WO-A-98/27049 beschrieben sind, worin die Symbole und Indizes folgende Bedeutungen haben: S8) compounds of the formula (S8), as described in WO-A-98/27049, where the symbols and indices have the following meanings:
RD 1 ist Halogen, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, 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,
RD 2 ist Wasserstoff oder (C1-C4)Alkyl, R D 2 is hydrogen or (C 1 -C 4 ) alkyl,
RD 3 ist Wasserstoff, (C1-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; oder deren Salze, 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,
nD ist eine ganze Zahl von 0 bis 2. n D is an integer from 0 to 2.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. S9) Active ingredients from the class of the 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
1 ,2-Dihydro-4-hydroxy- 1 -ethyl-3 -(5 -tetrazolylcarbonyl)-2-chinolon (CAS-Reg .Nr.: 219479-18- 2), l,2-Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 1, 2-Dihydro-4-hydroxy- 1 -ethyl-3 - (5 -tetrazolylcarbonyl) -2-quinolone (CAS-Reg .Nr .: 219479-18-2), l, 2-Dihydro-4-hydroxy- l-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Reg. No.
95855-00-8), wie sie in der WO-A- 1999/000020 beschrieben sind. 95855-00-8), as described in WO-A-1999/000020.
S10) Verbindungen der Formeln (S10a) oder (S10b), S10) compounds of the formulas (S10 a ) or (S10 b ),
wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind, as described in WO-A-2007/023719 and WO-A-2007/023764,
Figure imgf000036_0001
Figure imgf000036_0001
(S10a) (S10b) (S10 a ) (S10 b )
worin wherein
RE 1 Halogen, (C1-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 R E 1 halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
YE, ZE unabhängig voneinander O oder S, Y E , Z E independently of one another O or S,
nE eine ganze Zahl von 0 bis 4, n E is an integer from 0 to 4,
RE 2 (C1-C16)Alkyl, (C2-C6 -Alkenyl. (C3-C)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, R E 2 (C 1 -C 16 ) alkyl, (C 2 -C 6 -alkenyl. (C 3 -C) cycloalkyl, aryl; benzyl, halobenzyl,
RE 3 Wasserstoff oder (C1-C6) Alkyl bedeuten. R E 3 is hydrogen or (C 1 -C 6 ) alkyl.
S11) Wirkstoffe vom Typ der Oxyimino- Verbindungen (S11), die als Saatbeizmittel bekannt sind, wie z. B. 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), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, "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,
"Fluxofenim" ( 1 -(4-Chlorphenyl)-2,2,2-trifluor- 1 -ethanon-0-( 1 ,3 -dioxolan-2-ylmethyl)-oxim) (S 11-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (Sl l-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. "Fluxofenim" (1 - (4-chlorophenyl) -2,2,2-trifluoro-1 -ethanon-0- (1,3-dioxolan-2-ylmethyl) -oxime) (S 11-2), which is used as a seed dressing -Safener for millet is known against damage by metolachlor, and "Cyometrinil" or "CGA-43089" ((Z) -Cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.
S12) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl- [(3 -oxo-lH-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S 12-1) und verwandte Verbindungen aus WO-A-1998/13361. 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.
S13) Eine oder mehrere Verbindungen aus Gruppe (S13): S13) One or more compounds from group (S13):
"Naphthalic anhydrid" (1,8-Naphthalindicarbonsäureanhydrid) (S 13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "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,
"Fenclorim" (4, 6-Dichlor-2 -phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,
"Flurazole" (Benzyl-2-chlor-4-trifluormethyl-l,3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist, "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,
"CF 304415" (CAS-Reg.Nr. 31541-57-8) "CF 304415" (CAS Reg. No. 31541-57-8)
(4-Carboxy-3,4-dihydro-2H-l-benzopyran-4-essigsäure) (S13-4) der Firma American (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American
Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, Cyanamide, which is known as a safener for corn against damage from imidazolinones,
"MG 191" (CAS-Reg.Nr. 96420-72-3) (2-Dichlormethyl-2-methyl-l,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "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,
"MG 838" (CAS-Reg.Nr. 133993-74-5) "MG 838" (CAS Reg. No. 133993-74-5)
(2-propenyl l-oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia "Disulfoton" (0,0-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), (2-propenyl l-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia "Disulfoton" (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
"Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (S13-8), "Dietholate" (O, O-Diethyl-O-phenylphosphorothioate) (S13-8),
"Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9). "Mephenate" (4-chlorophenyl methyl carbamate) (S13-9).
S14) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. S14) Active ingredients which, in addition to a herbicidal action against harmful plants, also have a safener effect on crop plants such as rice, such as. B.
"Dimepiperate" oder "MY-93" (S- 1 -Methyl- 1 -phenylethyl-piperidin- 1 -carbothioat). das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Dimepiperate" or "MY-93" (S-1 -methyl-1-phenylethyl-piperidine-1-carbothioate). known as a safener for rice against damage from the herbicide Molinate,
"Daimuron" oder "SK 23" (1-(1 Methyl-l-phenylethyl)-3-p-tolyl-hamstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist, "Daimuron" or "SK 23" (1- (1-methyl-l-phenylethyl) -3-p-tolyl-urea), which is known as a safener for rice against damage by the herbicide imazosulfuron,
"Cumyluron" = "JC-940" (3-(2-Chlorphenylmethyl)-1-(1-methyl-1-phenyl-ethyl)hamstoff, siehe JP-A-60087270), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenyl-ethyl) urea, see JP-A-60087270), which is used as a safener for rice against damage of some herbicides is known, "methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against the damage of some herbicides,
"CSB" (l-Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091-06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. "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.
S 15) Verbindungen der Formel (S 15) oder deren Tautomere,
Figure imgf000038_0001
S 15) compounds of the formula (S 15) or their tautomers,
Figure imgf000038_0001
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind, as described in WO-A-2008/131861 and WO-A-2008/131860,
worin wherein
RH 1 einen (C1-C6)Haloalkylrest bedeutet und R H 1 denotes a (C 1 -C 6 ) haloalkyl radical and
RH 2 Wasserstoff oder Halogen bedeutet und R H 2 is hydrogen or halogen and
RH 3, RH 4 unabhängig voneinander Wasserstoff, (C1-C16)Alkyl, (C2-C16)Alkenyl oder R H 3 , R H 4 independently of one another are hydrogen, (C 1 -C 16 ) alkyl, (C 2 -C 16 ) alkenyl or
(C2-C16)Alkinyl, (C 2 -C 16 ) alkynyl,
wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylamino, Di[(C1-C4)alkyl]-amino, [(C1-C4)Alkoxy]- carbonyl, [(C1-C4)Haloalkoxy]-carbonyl, (C3-C6)Cycloalkyl. das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, where 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,
oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (G-G)Cycloalkyl. das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, or (C 3 -C 6 ) cycloalkyl, (C 4 -C 6 ) cycloalkenyl, (GG) cycloalkyl. which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 ) cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring is
wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (C1-C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy, (C1-C4)Alkylthio, (C1-C4)Alkylamino, Di[(C1- C4)alkyl]-amino, [(C1-C4)Alkoxy]-carbonyl, [(C1-C4)Haloalkoxy]-carbonyl, where 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,
(C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, (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,
bedeutet oder means or
RH 3 (C1-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet undR H 3 is (C 1 -C 4 ) -alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C) alkynyloxy or (C 2 -C 4 ) haloalkoxy and
RH 4 Wasserstoff oder (C1-C4)-Alkyl bedeutet oder R H 4 is hydrogen or (C 1 -C 4 ) -alkyl or
RH 3 und RH 4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen R H 3 and R H 4 together with the directly bonded N atom form a four- to eight-membered
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (C1- C4)Alkyl, (C1-C4)Haloalkyl, (C1-C4)Alkoxy, (C1-C4)Haloalkoxy und (C1-C4)Alkylthio substituiert ist, bedeutet. 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.
S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z. B. S16) Active ingredients that are primarily used as herbicides, but also have a safener effect on crops, e.g. B.
(2,4-Dichlorphenoxy)essigsäure (2,4-D), (2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-Chlorphenoxy)essigsäure, (4-chlorophenoxy) acetic acid,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop), (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (Mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
(4-Chlor-o-tolyloxy)essigsäure (MCPA), (4-chloro-o-tolyloxy) acetic acid (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure, 4- (4-chloro-o-tolyloxy) butyric acid,
4-(4-Chlorphenoxy)buttersäure, 4- (4-chlorophenoxy) butyric acid,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba), 3,6-dichloro-2-methoxybenzoic acid (Dicamba),
l-(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl). 1- (ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).
Bevorzugte Safener in Kombination mit den erfindungsgemäßen Verbindungend der allgemeinen Formel (I) und/oder deren Salze, insbesondere mit den Verbindungen der Formeln (1-1) bis (1-19) und/oder deren Salze sind: Cloquintocet-mexyl, Cyprosulfamid, Fenchlorazol-ethylester, Isoxadifen- ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 und S4-5, und besonders bevorzugte Safener sind: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl und Mefenpyr-diethyl. 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.
Biologische Beispiele Biological examples
A. Herbizide Wirkung im Nachauflauf A. Post-emergence herbicidal effects
Samen von mono- bzw. dikotylen Unkrautpflanzen wurden in Kunststofftöpfen in sandigem Lehmboden ausgelegt (Doppelaussaaten mit jeweils einer Spezies mono- bzw. dikotyler Unkrautpflanzen pro Topf), mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden als wässrige Suspension bzw. Emulsion, unter Zusatz von 0,5% Additiv, mit einer Wasseraufwandmenge von umgerechnet 600 Liter pro Hektar, auf die grünen Pflanzenteile appliziert. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Seeds of monocotyledonous and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (double sowing with one species of monocotyledonous or dicotyledonous weed plants per pot), covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated in the single-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were applied to the green parts of the plant as an aqueous suspension or emulsion, with the addition of 0.5% additive, with a water application rate of 600 liters per hectare . After the test plants had stood in the greenhouse for about 3 weeks, under optimal growth conditions, the effect of the preparations was rated visually in comparison with untreated controls.
Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie For example, 100% effect = plants have died, 0% effect = how
Kontrollpflanzen . In den nachstehenden Tabllen Al bis A12 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1280 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Control plants. 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.
Tabelle Al : Nachauflaufwirkung gegen Echinochloa crus-galli (ECHCG) Table Al: Post-emergence effect against Echinochloa crus-galli (ECHCG)
Figure imgf000040_0001
Figure imgf000040_0001
Tabelle A2: Nachauflaufwirkung gegen Lolium rigidum (LOLRI) Table A2: Post-emergence effects against Lolium rigidum (LOLRI)
Figure imgf000040_0002
Tabelle A3: Nachauflaufwirkung gegen Poa annua (POAAN)
Figure imgf000040_0002
Table A3: Post-emergence effects against Poa annua (POAAN)
Figure imgf000040_0003
Tabelle A4: Nachauflaufwirkung gegen Setaria viridis (SETVI)
Figure imgf000040_0003
Table A4: Post-emergence effects against Setaria viridis (SETVI)
Figure imgf000041_0001
Figure imgf000041_0001
Tabelle A5 : Nachauflaufwirkung gegen Abutilon theophrasti (ABUTH)
Figure imgf000041_0002
Table A5: Post-emergence effects against Abutilon theophrasti (ABUTH)
Figure imgf000041_0002
Tabelle A6: Nachauflaufwirkung gegen Amaranthus retroflexus (AMARE)
Figure imgf000041_0003
Tabelle A7 : Nachauflaufwirkung gegen Matricaria inodora (MATIN)
Figure imgf000042_0001
Table A6: Post-emergence effect against Amaranthus retroflexus (AMARE)
Figure imgf000041_0003
Table A7: Post-emergence effects against Matricaria inodora (MATIN)
Figure imgf000042_0001
Tabelle A8: Nachauflaufwirkung gegen Stellaria media (STEME)
Figure imgf000042_0002
Table A8: Post-emergence effects against Stellaria media (STEME)
Figure imgf000042_0002
Tabelle A9: Nachauflaufwirkung gegen Alopecurus myosuroides (ALOMY)
Figure imgf000042_0003
Tabelle A10: Nachauflaufwirkung gegen Digitaria sanguinalis (DIGSA) Table A9: Post-emergence effects against Alopecurus myosuroides (ALOMY)
Figure imgf000042_0003
Table A10: Post-emergence effects against Digitaria sanguinalis (DIGSA)
Figure imgf000043_0001
Figure imgf000043_0001
Tabelle Al l : Nachauflaufwirkung gegen Bassia scoparia (KCHSC) Table Al l: Post-emergence effects against Bassia scoparia (KCHSC)
Figure imgf000043_0002
Figure imgf000043_0002
Tabelle A12: Nachauflaufwirkung gegen Veronica persica (VERPE) Table A12: Post-emergence effects against Veronica persica (VERPE)
Figure imgf000043_0003
Figure imgf000043_0003
Wie die Ergebnisse der Tabellen Al -Al 2 beispielhaft zeigen, weisen die erfindungsgemäßen As the results of Tables Al -Al 2 show by way of example, the inventive
Verbindungen Nr. 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17 und 1-19 bei Behandlung im Nachauflauf eine sehr gute herbizide Wirksamkeit gegen die Schadpflanzen Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME), Alopecurus myosuroides (ALOMY), Digitaria sanguinalis (DIGSA), Bassia scoparia (KCHSC) und Veronica persica (VERPE) bei einer Aufwandmenge von 1280 g Aktivsubstanz pro Hektar auf. Compounds No. 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15 , 1-16, 1-17 and 1-19 with post-emergence treatment a very good herbicidal activity against the harmful plants Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME), Alopecurus myosuroides (ALOMY), Digitaria sanguinalis (DIGSA), Bassia scoparia (KCHSC) and Veronica persica (VERPE) at an application rate of 1280 g of active ingredient per hectare.
Herbizide Wirkung im Nachauflauf Post-emergence herbicidal effect
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen wurden in Kunststoff- oder organischen Pflanztöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfmdungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Seeds of monocotyledonous or dicotyledonous weed or crop plants were placed in plastic or organic plant pots in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated in the single-leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of 600 l / ha. After the test plants had stood in the greenhouse for about 3 weeks, under optimal growth conditions, the effect of the preparations was rated visually in comparison with untreated controls. For example, 100% activity means = plants have died, 0% activity = like control plants.
In nachstehenden Tabellen Bl bis B8 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 320 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. 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.
Tabelle Bl : Nachauflaufwirkung gegen Alopecurus myosuroides (ALOMY) Table B1: Post-emergence effects against Alopecurus myosuroides (ALOMY)
Figure imgf000044_0001
Figure imgf000044_0001
Tabelle B2: Nachauflaufwirkung gegen Echinochloa crus-galli (ECHCG) Table B2: Post-emergence effects against Echinochloa crus-galli (ECHCG)
Figure imgf000044_0002
Tabelle B3 : Nachauflaufwirkung gegen Setaria viridis (SETVI)
Figure imgf000045_0001
Figure imgf000044_0002
Table B3: Post-emergence effects against Setaria viridis (SETVI)
Figure imgf000045_0001
Tabelle B4: Nachauflaufwirkung gegen Amaranthus retroflexus (AMARE)
Figure imgf000045_0002
Table B4: Post-emergence effect against Amaranthus retroflexus (AMARE)
Figure imgf000045_0002
Tabelle B5 : Nachauflaufwirkung gegen Pharbitis purpurea (PHBPU)
Figure imgf000045_0003
Table B5: Post-emergence effect against Pharbitis purpurea (PHBPU)
Figure imgf000045_0003
Tabelle B6: Nachauflaufwirkung gegen Polygonum convolvulus (POLCO)
Figure imgf000045_0004
Table B6: Post-emergence effect against Polygonum convolvulus (POLCO)
Figure imgf000045_0004
Tabelle B7: Nachauflaufwirkung gegen Viola tricolor (VIOTR)
Figure imgf000045_0005
Tabelle B8: Nachauflaufwirkung gegen Veronica persica (VERPE) Table B7: Post-emergence effects against Viola tricolor (VIOTR)
Figure imgf000045_0005
Table B8: Post-emergence effects against Veronica persica (VERPE)
Figure imgf000046_0001
Figure imgf000046_0001
Wie die Ergebnisse der Tabellen B1-B8 beispielhaft zeigen, weisen die erfmdungsgemäßen As the results of Tables B1-B8 show by way of example, the inventive
Verbindungen Nr. 1-2, 1-5, 1-6, 1-11 und 1-12 bei Behandlung im Nachauflauf eine sehr gute herbizide Wirksamkeit gegen die Schadpflanzen Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Setaria viridis (SETVI), Amaranthus retroflexus (AMARE), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Viola tricolor (VIOTR) und Veronica persica (VERPE) bei einer Aufwandmenge von 320 g Aktivsubstanz pro Hektar auf. Compounds No. 1-2, 1-5, 1-6, 1-11 and 1-12 in the case of post-emergence treatment have a very good herbicidal activity against the harmful plants Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Setaria viridis (SETVI), Amaranthus retroflexus (AMARE), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Viola tricolor (VIOTR) and Veronica persica (VERPE) at an application rate of 320 g of active ingredient per hectare.
C. Herbizide Wirkung im Vorauflauf C. Pre-emergence herbicidal effect
Samen von mono- und dikotylen Unkrautpflanzen wurden in Kunststofftöpfen, in sandigem Seeds of monocotyledon and dicotyledon weed plants were placed in plastic pots, in sandy
Lehmboden, ausgelegt (Doppelaussaaten mit jeweils eine Spezies mono- bzw. dikotyler Clay soil, laid out (double sowing with one species each mono- or dicotyledonous
Unkrautpflanzen pro Topf) und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfmdungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion, unter Zusatz von 0,5% Additiv, mit einer Wasseraufwandmenge von umgerechnet 600 Liter pro Hektar auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca. 3 Wochen wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Weed plants per pot) 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 liters per hectare applied. After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was rated visually in percentage values in comparison with untreated controls.
Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie For example, 100% effect = plants have died, 0% effect = how
Kontrollpflanzen . Control plants.
In nachstehenden Tabellen CI bis C12 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1280 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Tabelle CI : Vorauflaufwirkung gegen Echinochloa crus-galli (ECHCG)
Figure imgf000047_0001
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 CI: Pre-emergence effects against Echinochloa crus-galli (ECHCG)
Figure imgf000047_0001
Tabelle C2: Vorauflaufwirkung gegen Lolium rigidum (LOLRI)
Figure imgf000047_0002
Table C2: Pre-emergence effect against Lolium rigidum (LOLRI)
Figure imgf000047_0002
Tabelle C3: Vorauflaufwirkung gegen Poa annua (POAAN)
Figure imgf000047_0003
Tabelle C4 : Vorauflaufwirkung gegen Setaria viridis (SETVI)
Figure imgf000048_0001
Table C3: Pre-emergence effects against Poa annua (POAAN)
Figure imgf000047_0003
Table C 4 : Pre-emergence effects against Setaria viridis (SETVI)
Figure imgf000048_0001
Tabelle C5: Vorauflaufwirkung gegen Abutilon theophrasti (ABUTH)
Figure imgf000048_0002
Table C5: Pre-emergence effects against Abutilon theophrasti (ABUTH)
Figure imgf000048_0002
Tabelle C6: Vorauflaufwirkung gegen Amaranthus retroflexus (AMARE)
Figure imgf000049_0001
Table C6: Pre-emergence effect against Amaranthus retroflexus (AMARE)
Figure imgf000049_0001
Tabelle C7: Vorauflaufwirkung gegen Matricaria inodora (MATIN)
Figure imgf000049_0002
Tabelle C8: Vorauflaufwirkung gegen Stellaria media (STEME)
Figure imgf000050_0001
Table C7: Pre-emergence effects against Matricaria inodora (MATIN)
Figure imgf000049_0002
Table C8: Pre-emergence effects against Stellaria media (STEME)
Figure imgf000050_0001
Tabelle C9: Vorauflaufwirkung gegen Alopecurus myosuroides (ALOMY)
Figure imgf000050_0002
Table C9: Pre-emergence effects against Alopecurus myosuroides (ALOMY)
Figure imgf000050_0002
Tabelle CIO: Vorauflaufwirkung gegen Digitaria sanguinalis (DIGSA)
Figure imgf000050_0003
Tabelle CI 1: Vorauflaufwirkung gegen Bassia scoparia (KCHSC) Table CIO: Pre-emergence effects against Digitaria sanguinalis (DIGSA)
Figure imgf000050_0003
Table CI 1: Pre-emergence effect against Bassia scoparia (KCHSC)
Figure imgf000051_0001
Figure imgf000051_0001
Tabelle C12: Vorauflaufwirkung gegen Veronica persica (VERPE) Table C12: Pre-emergence effects against Veronica persica (VERPE)
Figure imgf000051_0002
Wie die Ergebnisse der Tabellen CI -CI 2 beispielhaft zeigen, weisen die erfindungsgemäßen
Figure imgf000051_0002
As the results of Tables CI-CI 2 show by way of example, the inventive
Verbindungen Nr. 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16 und 1-17 bei Behandlung im Vorauflauf eine sehr gute herbizide Wirksamkeit gegen die Schadpflanzen Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME), Alopecurus myosuroides (ALOMY), Digitaria sanguinalis (DIGSA), Bassia scoparia (KCHSC) und Veronica persica (VERPE) bei einer Aufwandmenge von 1280 g Aktivsubstanz pro Hektar auf. Herbizide Wirkung im Vorauflauf Compounds No. 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15 , 1-16 and 1-17 with pre-emergence treatment a very good herbicidal activity against the harmful plants Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Matricaria inodora (MATIN ), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME), Alopecurus myosuroides (ALOMY), Digitaria sanguinalis (DIGSA), Bassia scoparia (KCHSC) and Veronica persica (VERPE) at an application rate of 1280 g of active ingredient per hectare. Pre-emergence herbicidal effect
Samen von mono- bzw. dikotylen Unkraut und Kulturpflanzen wurden in Kunststoff- oder organischen Pflanztöpfen ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfmdungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca. 3 Wochen wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. 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. After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was rated visually in percentage values in comparison with untreated controls. For example, 100% activity means = plants have died, 0% activity = like control plants.
In nachstehenden Tabellen Dl bis D12 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 320 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. 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.
Tabelle Dl : Vorauflaufwirkung gegen Alopecurus myosuroides (ALOMY) Table Dl: Pre-emergence effects against Alopecurus myosuroides (ALOMY)
Figure imgf000052_0001
Tabelle D2: Vorauflaufwirkung gegen Digitaria sanguinalis (DIGSA)
Figure imgf000052_0001
Table D2: Pre-emergence effects against Digitaria sanguinalis (DIGSA)
Figure imgf000052_0002
Figure imgf000052_0002
Tabelle D3: Vorauflaufwirkung gegen Echinocloa crus-galli (ECHCG) Table D3: Pre-emergence effects against Echinocloa crus-galli (ECHCG)
Figure imgf000052_0003
Tabelle D4: Vorauflaufwirkung gegen Lolium rigidum (LOLRI)
Figure imgf000053_0001
Figure imgf000052_0003
Table D4: Pre-emergence effect against Lolium rigidum (LOLRI)
Figure imgf000053_0001
Tabelle D5 : Vorauflaufwirkung gegen Setaria viridis (SETVI)
Figure imgf000053_0002
Table D5: Pre-emergence effects against Setaria viridis (SETVI)
Figure imgf000053_0002
Tabelle D6: Vorauflaufwirkung gegen Abutilon theophrasti (ABUTH)
Figure imgf000053_0003
Table D6: Pre-emergence effects against Abutilon theophrasti (ABUTH)
Figure imgf000053_0003
Tabelle D7: Vorauflaufwirkung gegen Amaranthus retroflexus (AMARE)
Figure imgf000053_0004
Tabelle D8: Vorauflaufwirkung gegen Matricaria inodora (MATIN)
Figure imgf000054_0001
Table D7: Pre-emergence effect against Amaranthus retroflexus (AMARE)
Figure imgf000053_0004
Table D8: Pre-emergence effects against Matricaria inodora (MATIN)
Figure imgf000054_0001
Tabelle D9: Vorauflaufwirkung gegen Pharbitis purpurea (PHBPU) Table D9: Pre-emergence effects against Pharbitis purpurea (PHBPU)
Figure imgf000054_0002
Figure imgf000054_0002
Tabelle D10: Vorauflaufwirkung gegen Polygonum convolvulus (POLCO)
Figure imgf000054_0003
Table D10: Pre-emergence effect against Polygonum convolvulus (POLCO)
Figure imgf000054_0003
Tabelle D11 : Vorauflaufwirkung gegen Viola tricolor (VIOTR)
Figure imgf000054_0004
Table D11: Pre-emergence effects against Viola tricolor (VIOTR)
Figure imgf000054_0004
Tabelle D12: Vorauflaufwirkung gegen Veronica persica (VERPE)
Figure imgf000054_0005
Wie die Ergebnisse der Tabellen Dl -Dl 2 beispielhaft zeigen, weisen die erfmdungsgemäßen Table D12: Pre-emergence effects against Veronica persica (VERPE)
Figure imgf000054_0005
As the results of Tables Dl -Dl 2 show by way of example, the inventive
Verbindungen Nr. 1-2, 1-5, 1-6, 1-11 und 1-12 bei Behandlung im Vorauflauf eine sehr gute herbizide Wirksamkeit gegen die Schadpflanzen Alopecurus myosuroides (ALOMY), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Setaria viridis (SETVI), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Matricaria inodora (MATIN),Compounds No. 1-2, 1-5, 1-6, 1-11 and 1-12, when treated pre-emergence, have very good herbicidal activity against the harmful plants Alopecurus myosuroides (ALOMY), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Setaria viridis (SETVI), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Matricaria inodora (MATIN),
Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Viola tricolor (VIOTR) und Veronica persica (VERPE) bei einer Aufwandmenge von 320 g Aktivsubstanz pro Hektar auf. Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Viola tricolor (VIOTR) and Veronica persica (VERPE) at an application rate of 320 g of active ingredient per hectare.

Claims

Patentansprüche Claims
1 Substituierte Pyridinyloxypyridine der allgemeinen Formel (I) oder deren Salze 1 Substituted pyridinyloxypyridines of the general formula (I) or their salts
Figure imgf000056_0001
Figure imgf000056_0001
worin wherein
R1 für Wasserstoff, Cyano, (C1-C4)-Alkyl, (C1-C6)-Cycloalkyl, (C1-C4)-Flaloalkyl, (C1-C4)- Alkenyl, (C1-C4)-Alkynyl oder Halogen steht, und R 1 for hydrogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 6 ) -cycloalkyl, (C 1 -C 4 ) -flaoalkyl, (C 1 -C 4 ) -alkenyl, (C 1 -C 4 ) -alkynyl or halogen, and
R2, R3, R4 und R5 unabhängig voneinander für Wasserstoff, Nitro, Amino, Hydroxy, Cyano, Halogen, Formyl, Carboxyl, (C1-C4)-Alkyl, (C1-C4)-Haloalkyl, (C1-C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C4)-Alkynyl, (C2-C4)-Haloalkynyl, (C1-C4)- Alkoxy-(C1-C4)-alkyl, (C1-C4)-Haloalkoxy-(C1-C4)-alkyl, (C1-C4)-Alkylthio-(C1-C4)- alkyl, (C1-C4)-Alkylsulfmyl-(C1-C4)-a]kyl, (C1-C4)-Alkylsulfonyl-(C1-C4)-alkyl, (C1-C4)-Alkylcarbonyl, (C1-C4)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, (C1-C4)-Alkoxycarbonyl, (C2-C4)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (C2-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, (C1-C4)-Alkoxy, (C1-C4)-Haloalkoxy, (C1-C4)-Cycloalkoxy, (C1-C4)-Alkylcarbonyloxy, (C1-C4)-Haloalkylcarbonyloxy, (C1-C4)-Alkylamino, (C2-C6)-Dialkylamino, Formylamino, (C1-C4)-Alkylcarbonylamino, (C1-C4)- Haloalkylcarbonylamino, (C1-C4)-Alkoxycarbonylamino, (C1-C4)-Alkylsulfonylamino, (C1-C4)-Alkylthio, (C1-C4)-Haloalkylthio, (C3-C4)-Cycloalkylthio, (C1-C4)- Alkylsulfinyl, (C1-C4)-Haloalkylsulfinyl, (C3-C4)-Cycloalkylsulfinyl, (C1-C4)- Alkylsulfonyl, (C1-C4)-Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (C1-C4)- Alkylaminosulfonyl, (C2-C6)-Dialkylaminosulfonyl oder (C1-C6)-Trialkylsilyl stehen. 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 ) - alkyl, (C 1 -C 4 ) -Alkylsulfmyl- (C 1 -C 4 ) -a] kyl, (C 1 -C 4 ) -Alkylsulfonyl- (C 1 -C 4 ) - alkyl, (C 1 -C 4 ) -alkylcarbonyl, (C 1 -C 4 ) -haloalkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbonyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 2 -C 4 ) - Haloalkoxycarbonyl, (C 3 -C 6 ) -cycloalkoxycarbonyl, (C 2 -C 4 ) -alkylaminocarbonyl, (C 2 -C 6 ) -dialkylaminocarbonyl, (C 3 -C 6 ) - cycloalkylaminocarbonyl, (C 1 -C 4 ) - Alkoxy, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -cycloalkoxy, (C 1 -C 4 ) -alkylcarbonyloxy, (C 1 -C 4 ) -haloalkylcarbonyloxy, (C 1 -C 4 ) - Alkylamino, (C 2 -C 6 ) -dialkylamino, formylamino, (C 1 -C 4 ) -alkylcarbonyl amino, (C 1 -C 4 ) - haloalkylcarbonylamino, (C 1 -C 4 ) -alkoxycarbonylamino, (C 1 -C 4 ) -alkylsulfonylamino, (C 1 -C 4 ) -alkylthio, (C 1 -C 4 ) - haloalkylthio, (C 3 -C 4) cycloalkylthio, (C 1 -C 4) - alkylsulfinyl, (C 1 -C 4) haloalkylsulfinyl, (C 3 -C 4) cycloalkylsulfinyl, (C 1 -C 4) - Alkylsulfonyl, (C 1 -C 4 ) -haloalkylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, (C 1 -C 4 ) -alkylaminosulfonyl, (C 2 -C 6 ) -dialkylaminosulfonyl or (C 1 -C 6 ) - Trialkylsilyl stand.
2. Verbindung der allgemeinen Formel (I) nach Anspruch loder deren Salze, worin R1 für Wasserstoff, Cyano, Methyl oder Halogen steht, 2. A compound of the general formula (I) according to claim l or its salts, in which R 1 is hydrogen, cyano, methyl or halogen,
R2, R3, R4 und R5 unabhängig voneinander für Wasserstoff, Cyano, Halogen, (C1-C4)-Alkyl,R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen, cyano, halogen, (C 1 -C 4 ) -alkyl,
(C1-C4)-Haloalkyl, (C1-C6)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C4)- Alkynyl, (C2-C4)-Haloalkynyl, (C1-C4)-Alkoxy-(C1-C4)-alkyl, (C1-C4)-Haloalkoxy- (C1-C4)-alkyl, (C1-C4)-Alkylcarbonyl, (C1-C4)-Haloalkylcarbonyl, (C1-C4)- Alkoxycarbonyl, (C2-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (C1-C4)- Alkoxy, (C1-C4)-Haloalkoxy, (C1-C4)-Cycloalkoxy, (C1-C4)-Alkylthio oder (C1-C4)- Haloalkylthio stehen. (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 ) -alkoxycarbonyl, (C 2 -C 4 ) -alkylaminocarbonyl, (C 2 -C 6 ) -dialkylaminocarbonyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (C 1 -C 4 ) cycloalkoxy, (C 1 -C 4 ) alkylthio or (C 1 -C 4 ) haloalkylthio .
3. Verbindung der allgemeinen Formel (I) nach Anspruch 1 oder deren Salze, worin R1 für Wasserstoff oder Chlor steht, 3. A compound of the general formula (I) according to claim 1 or its salts, in which R 1 is hydrogen or chlorine,
R2 für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Methoxy steht, R 2 represents hydrogen, fluorine, chlorine, bromine, methyl or methoxy,
R3 für Wasserstoff, Chlor oder Methyl steht, R 3 represents hydrogen, chlorine or methyl,
R4 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl oder Methoxy steht, R 4 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy,
R5 für Wasserstoff oder Methyl steht. R 5 represents hydrogen or methyl.
4. Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. Herbicidal agents, characterized by a herbicidally active content of at least one compound of the general formula (I) according to any one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. Herbicidal compositions according to claim 4 in a mixture with formulation auxiliaries.
6. Herbizide Mittel nach Anspruch 4 oder 5 enthaltend mindestens einen weiteren pestizid wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und Wachstumsregulatoren. 6. Herbicidal compositions according to claim 4 or 5 containing at least one further pesticidally active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
7. Herbizide Mittel nach Anspruch 6 enthaltend einen Safener. 7. Herbicidal compositions according to claim 6 containing a safener.
8. Herbizide Mittel nach Anspruch 7 enthaltend Cyprosulfamid, Cloquintocet-mexyl, Mefenpyr- diethyl oder Isoxadifen-ethyl. 8. Herbicidal agents according to claim 7 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr- diethyl or isoxadifen-ethyl.
9. Herbizide Mittel nach einem der Ansprüche 4 bis 8 enthaltend ein weiteres Herbizid. 9. Herbicidal compositions according to one of claims 4 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels nach einem der Ansprüche 4 bis 9 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for combating unwanted plants, characterized in that an effective amount of at least one compound of the general formula (I) according to any one of claims 1 to 3 or a herbicidal composition according to any one of claims 4 to 9 is applied to the plants or to the site of unwanted plant growth.
11. Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach einem der Ansprüche 4 bis 9 zur Bekämpfung unerwünschter Pflanzen. 11. Use of compounds of the general formula (I) according to any one of claims 1 to 3 or of herbicidal compositions according to any one of claims 4 to 9 for combating undesirable plants.
12. Verwendung nach Anspruch 11, dadurch gekennzeichnet, daß die Verbindungen der 12. Use according to claim 11, characterized in that the compounds of
allgemeinen Formel (I) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden. general formula (I) for combating undesired plants in crops of useful plants.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 13. Use according to claim 12, characterized in that the useful plants are transgenic useful plants.
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Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (en) 1982-02-17 1983-08-24 Ciba-Geigy Ag Use of quinoline derivatives in the protection of crop plants
EP0094349A2 (en) 1982-05-07 1983-11-16 Ciba-Geigy Ag Use of quinoline derivatives for the protection of cultivated plants
US4493730A (en) 1982-09-10 1985-01-15 Ishihara Sangyo Kaisha, Ltd. Phenoxypyridine useful as a herbicide
JPS6087270A (en) 1983-09-26 1985-05-16 バイエル・アクチエンゲゼルシヤフト 1,3-diaryl-5-methylene-perhydropyrimidin-2-one
EP0174562A2 (en) 1984-09-11 1986-03-19 Hoechst Aktiengesellschaft Plant protecting agents based on 1,2,4 - triazole derivatives as well as 1,2,4-triazole derivatives
EP0191736A2 (en) 1985-02-14 1986-08-20 Ciba-Geigy Ag Use of quinoline derivatives for the protection of crop plants
EP0268554A2 (en) 1986-10-22 1988-05-25 Ciba-Geigy Ag 1,5-Diphenyl pyrazole-3-carbonic-acid derivatives for the protection of cultured plants
EP0269806A1 (en) 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Phenylpyrazole carbonic acid derivatives, their preparation and use as plant growth regulators and antidotes
EP0333131A1 (en) 1988-03-17 1989-09-20 Hoechst Aktiengesellschaft Plant protective agent based on pyrazolecarboxylic acid derivatives
EP0346620A1 (en) 1988-05-20 1989-12-20 Hoechst Aktiengesellschaft Plant protection agents containing 1,2,4-triazole derivatives, and the 1,2,4-triazole derivatives
EP0365484A1 (en) 1988-10-20 1990-04-25 Ciba-Geigy Ag Sulfamoyl phenyl ureas
WO1991008202A1 (en) 1989-11-25 1991-06-13 Hoechst Aktiengesellschaft Isoxazolines, method of preparation thereof, and their use as plant-protection agents
WO1991007874A1 (en) 1989-11-30 1991-06-13 Hoechst Aktiengesellschaft Pyrazolines for the protection of crops against herbicides
EP0492366A2 (en) 1990-12-21 1992-07-01 Hoechst Schering AgrEvo GmbH New 5-chloroquinolin-8-oxyalkanecarbonic acid derivatives, process for their preparation and their use as antidotes for herbicides
EP0582198A2 (en) 1992-08-01 1994-02-09 Hoechst Schering AgrEvo GmbH Substituted (hetero-)aryle compounds, process for their preparation, those containing compositions and their use as safeners
WO1995007897A1 (en) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Substituted isoxazolines, process for producing them, agents containing them and their use as safeners
WO1997045016A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Novel n-acyl sulphonamides, novel mixtures of herbicides and antidotes and their use
WO1998013361A1 (en) 1996-09-26 1998-04-02 Novartis Ag Herbicidal composition
WO1998027049A1 (en) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Novel 2-fluoroacrylic acid derivatives, novel mixtures of herbicides and antidotes and the use thereof
WO1998038856A1 (en) 1997-03-04 1998-09-11 Zeneca Limited Compositions for safening rice against acetochlor
WO1999000020A1 (en) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-tetrazolyl carbonyl)-2-quinolones and products for protecting useful plants containing the same
WO1999016744A1 (en) 1997-09-29 1999-04-08 Aventis Cropscience Gmbh Acylsulfamoyl benzoic acid amides, plant protection agents containing said acylsulfamoyl benzoic acid amides, and method for producing the same
WO2002034048A1 (en) 2000-10-23 2002-05-02 Syngenta Participations Ag Agrochemical compositions with quinoline safeners
WO2004084631A1 (en) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Use of aromatic hydroxy compounds as safeners
WO2005016001A1 (en) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Safener based on aromatic-aliphatic carboxylic acid derivatives
WO2005015994A1 (en) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Use of aromatic compounds as safeners
WO2005112630A1 (en) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Quinoxalin-2-one derivatives crop protection agents comprising the same and method for production and use therof
WO2007023764A1 (en) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent for reduction of harmful effect of herbicide and herbicide composition having reduced harmful effect
WO2007023719A1 (en) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent for reducing chemical injury and herbicide composition with reduced chemical injury
WO2008131860A2 (en) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridonecarboxamides crop protection agents containing the same method for production and use thereof
WO2008131861A1 (en) 2007-04-30 2008-11-06 Bayer Cropscience Ag Use of pyridine-2-oxy-3-carbonamides as safeners
CN101838227A (en) 2010-04-30 2010-09-22 孙德群 Safener of benzamide herbicide
WO2015086519A1 (en) 2013-12-09 2015-06-18 Ucb Biopharma Sprl Imidazopyridine derivatives as modulators of tnf activity

Patent Citations (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (en) 1982-02-17 1983-08-24 Ciba-Geigy Ag Use of quinoline derivatives in the protection of crop plants
EP0094349A2 (en) 1982-05-07 1983-11-16 Ciba-Geigy Ag Use of quinoline derivatives for the protection of cultivated plants
US4493730A (en) 1982-09-10 1985-01-15 Ishihara Sangyo Kaisha, Ltd. Phenoxypyridine useful as a herbicide
JPS6087270A (en) 1983-09-26 1985-05-16 バイエル・アクチエンゲゼルシヤフト 1,3-diaryl-5-methylene-perhydropyrimidin-2-one
EP0174562A2 (en) 1984-09-11 1986-03-19 Hoechst Aktiengesellschaft Plant protecting agents based on 1,2,4 - triazole derivatives as well as 1,2,4-triazole derivatives
EP0191736A2 (en) 1985-02-14 1986-08-20 Ciba-Geigy Ag Use of quinoline derivatives for the protection of crop plants
EP0269806A1 (en) 1986-10-04 1988-06-08 Hoechst Aktiengesellschaft Phenylpyrazole carbonic acid derivatives, their preparation and use as plant growth regulators and antidotes
EP0268554A2 (en) 1986-10-22 1988-05-25 Ciba-Geigy Ag 1,5-Diphenyl pyrazole-3-carbonic-acid derivatives for the protection of cultured plants
EP0333131A1 (en) 1988-03-17 1989-09-20 Hoechst Aktiengesellschaft Plant protective agent based on pyrazolecarboxylic acid derivatives
EP0346620A1 (en) 1988-05-20 1989-12-20 Hoechst Aktiengesellschaft Plant protection agents containing 1,2,4-triazole derivatives, and the 1,2,4-triazole derivatives
EP0365484A1 (en) 1988-10-20 1990-04-25 Ciba-Geigy Ag Sulfamoyl phenyl ureas
WO1991008202A1 (en) 1989-11-25 1991-06-13 Hoechst Aktiengesellschaft Isoxazolines, method of preparation thereof, and their use as plant-protection agents
WO1991007874A1 (en) 1989-11-30 1991-06-13 Hoechst Aktiengesellschaft Pyrazolines for the protection of crops against herbicides
EP0492366A2 (en) 1990-12-21 1992-07-01 Hoechst Schering AgrEvo GmbH New 5-chloroquinolin-8-oxyalkanecarbonic acid derivatives, process for their preparation and their use as antidotes for herbicides
EP0582198A2 (en) 1992-08-01 1994-02-09 Hoechst Schering AgrEvo GmbH Substituted (hetero-)aryle compounds, process for their preparation, those containing compositions and their use as safeners
WO1995007897A1 (en) 1993-09-16 1995-03-23 Hoechst Schering Agrevo Gmbh Substituted isoxazolines, process for producing them, agents containing them and their use as safeners
WO1997045016A1 (en) 1996-05-29 1997-12-04 Hoechst Schering Agrevo Gmbh Novel n-acyl sulphonamides, novel mixtures of herbicides and antidotes and their use
WO1998013361A1 (en) 1996-09-26 1998-04-02 Novartis Ag Herbicidal composition
WO1998027049A1 (en) 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh Novel 2-fluoroacrylic acid derivatives, novel mixtures of herbicides and antidotes and the use thereof
WO1998038856A1 (en) 1997-03-04 1998-09-11 Zeneca Limited Compositions for safening rice against acetochlor
WO1999000020A1 (en) 1997-06-27 1999-01-07 Hoechst Schering Agrevo Gmbh 3-(5-tetrazolyl carbonyl)-2-quinolones and products for protecting useful plants containing the same
WO1999016744A1 (en) 1997-09-29 1999-04-08 Aventis Cropscience Gmbh Acylsulfamoyl benzoic acid amides, plant protection agents containing said acylsulfamoyl benzoic acid amides, and method for producing the same
WO2002034048A1 (en) 2000-10-23 2002-05-02 Syngenta Participations Ag Agrochemical compositions with quinoline safeners
WO2004084631A1 (en) 2003-03-26 2004-10-07 Bayer Cropscience Gmbh Use of aromatic hydroxy compounds as safeners
WO2005016001A1 (en) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Safener based on aromatic-aliphatic carboxylic acid derivatives
WO2005015994A1 (en) 2003-08-05 2005-02-24 Bayer Cropscience Gmbh Use of aromatic compounds as safeners
WO2005112630A1 (en) 2004-05-12 2005-12-01 Bayer Cropscience Gmbh Quinoxalin-2-one derivatives crop protection agents comprising the same and method for production and use therof
WO2007023719A1 (en) 2005-08-22 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent for reducing chemical injury and herbicide composition with reduced chemical injury
WO2007023764A1 (en) 2005-08-26 2007-03-01 Kumiai Chemical Industry Co., Ltd. Agent for reduction of harmful effect of herbicide and herbicide composition having reduced harmful effect
WO2008131860A2 (en) 2007-04-30 2008-11-06 Bayer Cropscience Ag Pyridonecarboxamides crop protection agents containing the same method for production and use thereof
WO2008131861A1 (en) 2007-04-30 2008-11-06 Bayer Cropscience Ag Use of pyridine-2-oxy-3-carbonamides as safeners
CN101838227A (en) 2010-04-30 2010-09-22 孙德群 Safener of benzamide herbicide
WO2015086519A1 (en) 2013-12-09 2015-06-18 Ucb Biopharma Sprl Imidazopyridine derivatives as modulators of tnf activity

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
"Chemistry and Technology of Agrochemical Formulations", 1998, KLUWER ACADEMIC PUBLISHERS
"Perry's Chemical Engineer's Handbook", 1973, MCGRAW-HILL, pages: 8 - 57
"Spray-Drying Handbook", 1979, G. GOODWIN LTD.
"The Pesticide Manual", 2012, THE BRITISH CROP PROTECTION COUNCIL AND THE ROYAL SOC. OF CHEMISTRY
BRAUN ET AL., EMBO J., vol. 11, 1992, pages 3219 - 3227
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 133993-74-5
G.C. KLINGMAN: "Weed Control as a Science", 1961, JOHN WILEY AND SONS, INC., pages: 81 - 96
H.V. OLPHEN: "Handbook of Insecticide Dust Diluents and Carriers", 1963, J. WILEY & SONS
J.D. FREYERS.A. EVANS: "Weed Control Handbook", 1968, BLACKWELL SCIENTIFIC PUBLICATIONS, pages: 101 - 103
J.E. BROWNING: "Agglomeration", CHEMICAL AND ENGINEERING, 1967, pages 147 ff
SCHÖNFELDT: "Grenzflächenaktive Äthylenoxidaddukte", 1976, WISS. VERLAGSGESELLSCHAFT
SISLEYWOOD: "Encyclopedia of Surface Active Agents", 1964, CHEM. PUBL. CO. INC.
WEED RESEARCH, vol. 26, 1986, pages 441 - 445

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