EP1610611A1 - Use of aromatic hydroxy compounds as safeners - Google Patents

Use of aromatic hydroxy compounds as safeners

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Publication number
EP1610611A1
EP1610611A1 EP04721478A EP04721478A EP1610611A1 EP 1610611 A1 EP1610611 A1 EP 1610611A1 EP 04721478 A EP04721478 A EP 04721478A EP 04721478 A EP04721478 A EP 04721478A EP 1610611 A1 EP1610611 A1 EP 1610611A1
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EP
European Patent Office
Prior art keywords
carbonyl
alkyl
radical
formula
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP04721478A
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German (de)
French (fr)
Inventor
Udo Bickers
Lothar Willms
Erwin Hacker
Christopher Rosinger
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP1610611A1 publication Critical patent/EP1610611A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/55—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and esterified hydroxy groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/90—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl and carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups

Definitions

  • WO-A-92/11761 describes herbicide-biocide-antidote combinations, where the biocide can mean an insecticide, fungicide or nematicide and the antidotes are selected from the group of structurally different amides, generally including aromatic amides, in order to avoid " negative synergism "in the interaction of herbicide and biocide.
  • X is a divalent radical of the formula O, S or NR a or N-NR yes a nRb D , where R a and R b are as defined below,
  • Y is a group of the formula O, S, NR c or NR c -NR d R e , where R c , R d and R e are as defined below,
  • R is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclic radical which is unsubstituted or substituted, or acyl, and
  • Formula (I) also includes all stereoisomers of the compounds whose specific stereochemical configuration is not explicitly expressed by the formula, and their mixtures.
  • Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not specified separately in the general formulas (I).
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials are produced.
  • the compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H 2 SO or HNO 3 , but also oxalic acid or sulfonic acids, to a basic group, such as, for example, amino or alkylamino.
  • a suitable substituents which are present in deprotonated form such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can in turn be protonated, such as amino groups.
  • Salts can also be formed in that, in the case of suitable substituents, such as, for example, sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation which is suitable for agriculture.
  • salts are, 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 (quaternary) ammonium salts.
  • 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 (quaternary) ammonium salts.
  • a hydrocarbon radical is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, for example comprising the radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl , Naphthyl, indanyl, indenyl, etc .; The same applies to the hydrocarbonoxy radicals.
  • the hydrocarbon and hydrocarbonoxy radicals in the above definitions preferably have 1 to 20 C atoms, more preferably 1 to 16 C atoms, in particular 1 to 12 C atoms.
  • (-C-C) alkyl means a shorthand notation for open-chain alkyl having one to 4 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-C 6 ) alkyl” also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
  • the lower carbon skeletons for example those having 1 to 6 carbon atoms or unsaturated groups having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals;
  • Alkenyl means, for example, vinyl, allyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl, preferably allyl, 1-methylprop-2-en-1-
  • (C 2 -C 6 ) -alkynyl means, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2- in-1-yl, but-3-in-1-yl or 1-methyl-but-3-in-1-yl.
  • Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents also having a double bond on the cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included.
  • multi-cyclic 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 [2.1.0] pentan-2-yl, BicyclIo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C 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.
  • substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF2O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; unless otherwise defined, it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms.
  • the heterocyclic residue can e.g. be a heteroaromatic residue or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms.
  • heteroaromatic ring with a heteroatom from the group N, O and S for example pyridyl, pyrrolyl, thienyl or furyl; furthermore it is preferably a corresponding heteroaromatic ring with 2 or 3 heteroatoms, e.g. B. pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl and triazolyl.
  • It is furthermore preferably a partially or completely hydrogenated heterocyclic radical having a hetero atom from the group N, O and S, for example oxiranyl, oxetanyl, oxolanyl ( tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.
  • first substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • second substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • substituents mentioned by way of example can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • second substituent level can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • substituents mentioned by way of example can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined
  • Preferred substituents for the substituent levels are, for example
  • radicals with carbon atoms those with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred.
  • Substituents from the group halogen for example fluorine and chlorine, (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (CrC) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy or ethoxy, are generally preferred, (C ⁇ -C 4 ) haloalkoxy, nitro and Cyano.
  • the substituents methyl, methoxy, fluorine and chlorine are particularly preferred.
  • Acyl means, for example, formyl, alkylcarbonyl such as [(-CC 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic Acids.
  • alkylcarbonyl such as [(-CC 4 ) alkyl] carbonyl
  • phenylcarbonyl alkyloxycarbonyl
  • phenyloxycarbonyl benzyloxycarbonyl
  • alkylsulfonyl alkylsulfinyl
  • N-alkyl-1-iminoalkyl N-alkyl-1-iminoalkyl and other residues of organic Acids.
  • Acyl preferably means an acyl radical in the narrower sense, i.e. H. an organic acid residue in which the acid group is directly connected to the carbon atom of an organic residue, for example formyl, alkylcarbonyl such as acetyl or [(CrC) alkyl] carbonyl, phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other residues of organic acid
  • R 1 denotes a nitrile group (-CN).
  • R c , R d and R e are as defined below, and / or R is hydrogen, (C 8 -C 8 ) alkyl, (C 2 -C 18 ) alkenyl, (C 2 -C 18 ) alkynyl,
  • Hetero ring atoms and a total of 5 or 6 ring atoms, which is bonded to the group C ( X) with an N hetero ring atom and which can also contain hetero atoms from the group N, O and S in addition to the N atom in the yl position as hetero ring atoms and the unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (dG 4 ) alkyl, (dC 4 ) alkoxy, (d- d) haloalkyl, (C ⁇ -C 4 ) haloalkoxy, (dC 4 ) alkylthio and oxo is substituted, where each of the radicals R a , R b , R c , R d and R e in the radicals X and Y is each independently and independently of the radical R as defined for R or a radical of the formula - OR *, where R * is independent of R as defined for R, and / or R 2
  • C 4 ) alkyl (C 2 -C) alkenyl, (C 2 -C 4 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy , Amino, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (C ⁇ -C) alkylthio, (C ⁇ -C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyI, (CC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (C ⁇ -C 4 ) alkylamino, (C ⁇ -C 4 ) alkanoyl, (dC
  • R is hydrogen, (C 1 -C 2 ) alkyl, (C 2 -C 2 ) alkenyl, (C 2 -C 2 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) Cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (C ⁇ -C) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 4 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the Halogen, hydroxy group, (-C-C 4 ) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (d- C 4 ) alkylthio, (CC 4 ) Al
  • Y is a group of the formula O, S, NR C or NR c -NR d R e , preferably O or
  • Heterocyclyl- (dC 4 ) alkyl where each of the latter 9 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (Cr C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (dC 4 ) alkylamino, di (CrC 4 ) alkylamino, (C ⁇ -C 4 ) alkanoyl, (C ⁇ -C 4 ) haloalkanoyl, [(C ⁇ -C 4 ) alkoxy ] carbonyl and in the case of cyclic radicals also (-CC) alkyl and (-CC) haloalkyl is substituted, or (CrC 4 ) alkanoyl, (C ⁇ -C 4 ) haloalkan
  • R 1 preferably also denotes a radical of the formula
  • R 1 methoxy-acetiminocarbonyl, ethoxy-acetiminocarbonyl, n-propoxy-acetiminocarbonyl, isopropoxy-acetiminocarbonyl, (2-hydroxy-ethoxy) - acetiminocarbonyl, acetoxy-iminocarbonyl, acetoxy-methyliminocarbonyl, acetoxy-ethyliminocarbonyl, acetoxy-acetiminocarbonyl.
  • R 1 preferably also denotes a radical of the formula -CO-NR c R, in which R and R c are as defined above, preferably R is hydrogen, (CC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or Heterocyclyl- (dC 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (Cr C 4 ) haloalkoxy, (C 1 -C 4 ) alkyIthio, (-C-C 4 ) alkylsulfinyl,
  • R 3 (a) in the case n 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or
  • R 1 to R 5 have the meaning given and the radicals R 3 , R 4 and R 5 which are bonded to the oxygen atoms shown are each hydrogen or an acyl radical according to B 1 , B 2 or B 3 , preferably at least one of the oxygen bound radicals mean hydrogen.
  • the compounds of formula (I) can be prepared by derivatizing the hydroxybenzoates and their carboxyl derivatives as base compounds by conventional methods, e.g. B. acylated or etherified.
  • the advantageous effects of the compounds (I) according to the invention are observed if they are used together with the pesticides in the pre-emergence or in the post-emergence, for example with simultaneous application as a tank mix or as a co-formulation or with a separate application in parallel or in succession (split Application). It is also possible to repeat the application several times. Sometimes it can make sense to combine a pre-emergence application with a post-emergence application. Usually, the application is a post-emergence application to the crop or crop with simultaneous or later application of the pesticide.
  • the use of the compounds (I) according to the invention in seed dressing, the (immersion) treatment of seedlings or the treatment of other propagation material (for example potato tubers) is also suitable.
  • Insecticides that can cause plant damage alone or together with herbicides include the following:
  • Organophosphates e.g. Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate
  • Herbicides the phytotoxic side effects on crop plants of which can be reduced by means of compounds of the formula I, can be of very different structural classes and have very different mechanisms of action. Preference is given to commercially available herbicides, as described, for example, in the manual “The Pesticide Manual", 13th Edition 2003, The British Crop Protection Council and the e-Pesticide Manual Version 3 (2003) or also in the names are also referred to in the "Comp ⁇ ndium of Pesticide Common Names" (available on the Internet) and the literature cited there.
  • Triazine rings are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, where all substituents can be combined independently of one another.
  • alkoxyphenoxysulfonylureas e.g. B.
  • T) pyridinecarboxamides e.g. B. Diflufenican and Picolinafen;
  • Emulsifiable concentrates which are obtained by dissolving the active ingredients in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • emulsifiers are, for example, alkylarylsulfonic acid calcium salts, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters;
  • Granules such as water-soluble granules, water-dispersible granules and granules for spreading and soil application;
  • the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula I or a combination of safener and pesticide. They also contain 1 to 99.9, in particular 4 to 99.5% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25% by weight of a surfactant.
  • the active substance concentration in emulsifiable concentrates is the concentration of safener and / or pesticide, usually 1 to 90, in particular 5 to 80 wt .-%. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient.
  • the active substance concentration in wettable powders is generally 10 to 90% by weight.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • n-butyl n-Bu n-butyl
  • Seeds of various crops and weeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam.
  • the herbicides and the safeners in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were diluted to the required concentrations with deionized water and applied to the soil surface using a spray sled using a water application rate of 300 liters per hectare.
  • the safeners were used as 20 percent water-dispersible powders, the herbicide isoxaflutole as an aqueous suspension concentrate (see Table 1.1.1).

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Abstract

Disclosed are compounds of formula (I) or the salts thereof, wherein R<1> represents carboxy or a derivative of the carboxyl group, preferably a radical of formula -CN, -C(=X)-Y-R, or -C(=X)-Het wherein X represents a divalent radical of formula O, S, or NR<a> or N-NR<a>R<b>, R<a> and R<b> being defined as indicated in claim 1, while Y represents a group of formula O, S, NR<c>, or NR<c>-NR<d>R<e>, R<c>, R<d>, and R<e> being defined as indicated in claim 1, R<2>, R<3>, R<4>, R<5>, and R<6>, Z, Z', Z" are defined as indicated in claim 1, m represents an integer 0 or 1, n represents an integer 0 or 1, and o represents an integer 0 or 1, the sum m + n + o being an integer 1, 2, or 3. In case of the alternatives (b) defined above, at least one of the radicals R<3>, R<4>, and R<5> is selected among radicals of the group comprising hydrogen and acyl. The inventive compounds are suitable as safeners or resistance inducers for cultivated plants or useful plants, preferably as safeners against phytotoxic effects of agrochemicals, such as pesticides, on said plants.

Description

Verwendung von Hydroxyaromaten als SafenerUse of hydroxyaromatics as safener
Beschreibungdescription
Die vorliegende Erfindung betrifft das Gebiet der Safener oder Resistenzinduktoren zum Schützen von Kulturpflanzen oder Nutzpflanzen vor Schäden, die durch die Anwendung von Agrochemikalien wie Xenobioziden oder Bioziden, beispielsweise Herbiziden, Insektiziden, Akariziden, Nematiziden oder Fungiziden, Infektion durch Krankheitserreger wie Pilze, Bakterien, Viren oder auch durch schädliche Umweltfaktoren wie Trockenheit oder Dürre auftreten. Spezieller betrifft die Erfindung die neuartige Anwendung von bestimmten hydroxyaromatischen Verbindungen als Safener und neue Verbindungen aus dieser Gruppe.The present invention relates to the field of safeners or resistance inductors for protecting crop plants or useful plants from damage caused by the use of agrochemicals such as xenobiocides or biocides, for example herbicides, insecticides, acaricides, nematicides or fungicides, infection by pathogens such as fungi, bacteria, viruses or also occur due to harmful environmental factors such as drought or drought. More particularly, the invention relates to the novel use of certain hydroxyaromatic compounds as safeners and new compounds from this group.
Bei der Bekämpfung unerwünschter Organismen in land- und forstwirtschaftlichen Nutzpflanzenkulturen mit Pestiziden werden - in an sich unerwünschter Weise - häufig auch die Nutzpflanzen durch die verwendeten Pestizide mehr oder weniger stark geschädigt. Dieser Effekt tritt in besonderem Maße bei der Verwendung von zahlreichen Herbiziden - und dort in erster Linie bei der sogenannten Nachauflaufapplikation - in monokotylen und dikotylen Nutzpflanzenkulturen auf. Durch den Einsatz sogenannter "Safener" oder "Antidots" können in manchen Fällen die Nutzpflanzen gegen die phytotoxischen Eigenschaften der Pestizide geschützt werden, ohne daß die pestizide Wirkung gegenüber den Schadorganismen geschmälert wird.When combating undesirable organisms in agricultural and forestry crops with pesticides, the crops are often - to an extent undesirable - more or less severely damaged by the pesticides used. This effect occurs particularly when using numerous herbicides - and there primarily in the so-called post-emergence application - in monocotyledonous and dicotyledonous crops. The use of so-called "safeners" or "antidots" can in some cases protect the useful plants against the phytotoxic properties of the pesticides without reducing the pesticidal activity against the harmful organisms.
Die bislang als Safener bekannt gewordenen Verbindungen sind in ihrer Wirkung häufig auf bestimmte Kulturen und bestimmte Klassen von Pestiziden beschränkt. Insbesondere sind kaum kommerzielle Safener für dikotyle Kulturen bekannt geworden. Für ein Reihe von Pestiziden, sogenannte "nicht-selektive Herbizide" oder "Totalherbizide", sind ebenfalls kaum Safener beschrieben worden.The compounds known until now as safeners are often limited in their action to certain cultures and certain classes of pesticides. In particular, hardly any commercial safeners for dicot cultures have become known. Hardly any safeners have been described for a number of pesticides, so-called "non-selective herbicides" or "total herbicides".
US-A-4,808,208 beschreibt die Anwendung von Phenolen wie Mono- oder Dihydroxy-acetophenon oder Hydroxyzimtsäuren und einigen Derivaten dieser Carbonsäuren als Safener für Sojabohnenkulturen gegen phytotoxische Wirkungen des Herbizids Glyphosate (Phosphonomethylglyzin und dessen Salzen).US-A-4,808,208 describes the use of phenols such as mono- or dihydroxy-acetophenone or hydroxycinnamic acids and some derivatives thereof Carboxylic acids as safeners for soybean crops against the phytotoxic effects of the herbicide glyphosate (phosphonomethylglycine and its salts).
Außerdem ist aus der DE-A-19933897 bekannt, dass die Resistenz von Kulturpflanzen gegen chemischen Stress, ausgelöst durch die Anwendung von ungenügend selektiven Agrochemikalien, mittels Resistenzinduktoren aus der Gruppe der Acylcyclohexandione wie Prohexadion(-Salzen) und Trinexpac-ethyl oder -salzen oder Benzthiadiazolen oder Benzothiazolen oder deren Derivaten, wie Acibenzolar-S-methyl und Probenazol, verbessert werden kann.It is also known from DE-A-19933897 that the resistance of crop plants to chemical stress, triggered by the use of insufficiently selective agricultural chemicals, by means of resistance inducers from the group of acylcyclohexanediones, such as prohexadione (salts) and trinexpac-ethyl or salts or Benzthiadiazoles or benzothiazoles or their derivatives, such as acibenzolar-S-methyl and probenazole, can be improved.
Weiterhin ist bekannt, das Wuchstoffherbizide wie Dicamba (2,5-Dichloro-6- methoxy-benzoesäure) und Phenoxyalkancarbonsäurederivate (2,4-D, MCPA) in einigen Fällen als kulturpflanzenschützende Verbindungen für Ko-Herbizide eingesetzt worden sind (siehe z. B. US-A-5,846,902, US-A5,739,080, EP-A-512737).It is also known that growth herbicides such as dicamba (2,5-dichloro-6-methoxy-benzoic acid) and phenoxyalkane carboxylic acid derivatives (2,4-D, MCPA) have been used in some cases as crop protection compounds for co-herbicides (see e.g. US-A-5,846,902, US-A5,739,080, EP-A-512737).
US-A-4,321 ,084 beschreibt herbizide Mittel mit einem Gehalt an herbiziden Thiocarbamaten wie Vernolate oder Butylate in Kombination mit einem Antidot (= Safener) aus der Gruppe speziell halogenierter Phenole. Diese Phenole umfassen bekannte Herbizide wie die Hydroxybenzonitrile Bromoxynil und loxynil und auch solche Analoge, in denen die Nitrilgruppe durch eine Carboxy-, Carbalkoxy- oder Alkylgruppe ersetzt worden ist.US Pat. No. 4,321,084 describes herbicidal compositions containing herbicidal thiocarbamates such as vernolates or butylates in combination with an antidote (= safener) from the group of specially halogenated phenols. These phenols include known herbicides such as the hydroxybenzonitriles bromoxynil and loxynil and also analogs in which the nitrile group has been replaced by a carboxy, carbalkoxy or alkyl group.
WO-A-92/11761 beschreibt Herbizid-Biozid-Antidot-Kombinationen, wobei das Biozid ein Insektizid, Fungizid oder Nematizid bedeuten kann und die Antidote aus der Gruppe strukturell unterschiedlicher Amide, allgemein umfassend auch aromatische Amide, ausgewählt sind, zwecks Vermeidung von "negativem Synergismus " im Zusammenwirken von Herbizid und Biozid.WO-A-92/11761 describes herbicide-biocide-antidote combinations, where the biocide can mean an insecticide, fungicide or nematicide and the antidotes are selected from the group of structurally different amides, generally including aromatic amides, in order to avoid " negative synergism "in the interaction of herbicide and biocide.
Es wurde nun gefunden, dass überraschenderweise Verbindungen der nachstehend genannten Formel (I) oder deren Salzen aus der Gruppe bestimmter meta- oder para-Hydroxybenzoesäuren und deren Derivaten effektiv als Safener oder Resistenzinduktoren für Kultur- oder Nutzpflanzen verwendet werden können, vorzugsweise als Safener gegen Schäden von Agrochemikalien wie vorzugsweise Herbiziden an diesen Pflanzen.It has now been found that, surprisingly, compounds of the formula (I) below or their salts from the group of certain meta- or para-hydroxybenzoic acids and their derivatives can be used effectively as safeners or resistance inducers for crops or useful plants, preferably as a safener against damage to agrochemicals, such as preferably herbicides, on these plants.
Ein Gegenstand der Erfindung ist deshalb die Verwendung von aen der Formel (I) oder deren Salzen,The invention therefore relates to the use of aenes of the formula (I) or their salts,
worin wherein
R1 Carboxy oder ein Derivat der Carboxylgruppe, vorzugsweise einen Rest der FormelR 1 carboxy or a derivative of the carboxyl group, preferably a radical of the formula
-CN oder-CN or
-C(=X)-Y-R oder-C (= X) -Y-R or
-C(=X)-Het, in welcher X einen divalenten Rest der Formel O, S oder NRa oder N-NR jaanRbD bedeutet, wobei Ra und Rb wie unten definiert sind,-C (= X) -Het, in which X is a divalent radical of the formula O, S or NR a or N-NR yes a nRb D , where R a and R b are as defined below,
Y eine Gruppe der Formel O, S, NRc oder NRc-NRdRe bedeutet, wobei Rc, Rd und Re wie unten definiert sind,Y is a group of the formula O, S, NR c or NR c -NR d R e , where R c , R d and R e are as defined below,
R Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen heterocyclischen Rest, der unsubstituiert oder substituiert ist, oder Acyl bedeutet, undR is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclic radical which is unsubstituted or substituted, or acyl, and
Het einen aliphatischen N-Heterocyclus mit insgesamt 1 bis 4 Heteroringatomen bedeutet, der mit einem N-Heteroringatom an die Gruppe C(=X) gebunden ist und der als Heteroringatome neben dem N-Atom in der yl-Position noch Heteroatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder substituiert ist, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und unabhängig vom Rest R wie für R definiert ist oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, bedeutet, R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, SCN, CN oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oderHet means an aliphatic N-heterocycle with a total of 1 to 4 hetero ring atoms, which is bonded to the group C (= X) with an N-hetero ring atom and which, as hetero ring atoms, also contains hetero atoms from the group N in addition to the N atom in the yl position , O and S and which is unsubstituted or substituted, wherein each of the radicals R a , R b , R c , R d and R e in the radicals X and Y are each independently and independently of the radical R as defined for R. or a radical of the formula -OR *, where R * is independently of R as defined for R, R 2 and R 6 , each independently of one another, are hydrogen, halogen, SCN, CN or a hydrocarbon radical which is unsubstituted or substituted, R 3 (a) in the case n = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or
(b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder(b) in the case of n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case of m = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or
(b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und R5 (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oder(b) in the case m = 1 hydrogen or a radical of the formula A 2 , B 2 or C 2 and R 5 (a) in the case o = 0 hydrogen or a radical of the formula A 3 or B 3 or
(b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, einen(b) in the case o = 1, hydrogen or a radical of the formula A 3 , B 3 or C 3 , where each of the radicals A 1 , A 2 , A 3 , in each case independently of one another, has one
Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, bedeutet, jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, einen Acylrest bedeutet und jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen heterocyclischen Rest, der unsubstituiert oder substituiert ist, bedeutet, Z, Z', Z", jeweils unabhängig voneinander, eine Gruppe der Formel O, S(O)x oderHydrocarbon radical which is unsubstituted or substituted means each of the radicals B 1 , B 2 , B 3 , in each case independently of one another, is an acyl radical and each of the radicals C 1 , C 2 , C 3 , in each case independently of one another, is a heterocyclic radical, which is unsubstituted or substituted means, Z, Z ', Z ", in each case independently of one another, a group of the formula O, S (O) x or
NR', wobei x = 0, 1 oder 2 ist und R' Wasserstoff oder einenNR ', where x = 0, 1 or 2 and R' is hydrogen or one
Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einenHydrocarbon residue which is unsubstituted or substituted, or one
Kohlenwasserstoffoxyrest, der unsubstituiert oder substituiert ist, oder Acyl oder Acyloxy bedeutet, m eine ganze Zahl 0 oder 1 , n eine ganze Zahl 0 oder 1 und o eine ganze Zahl 0 oder 1 bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und B1, B2 beziehungweise B3 (= Acyl) ausgewählt ist, als Safener oder Resistenzinduktoren für Kultur- oder Nutzpflanzen, vorzugsweise als Safener gegen phytotoxische Wirkungen von Agrochemikalien, wie Pestiziden, an diesen Pflanzen.Hydrocarbonoxy radical which is unsubstituted or substituted, or means acyl or acyloxy, m is an integer 0 or 1, n is an integer 0 or 1 and o is an integer 0 or 1, the sum m + n + o being an integer 1, 2 or 3, and in the case of alternatives (b) defined above, at least one of the radicals R 3 , R 4 and R 5 consists of radicals from the group consisting of hydrogen and B 1 , B 2 or B 3 (= acyl) is selected as a safener or resistance inducer for crops or useful plants, preferably as a safener against phytotoxic effects of agrochemicals, such as pesticides, on these plants.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der Formel (I) umfasst.If the compounds can form tautomers by hydrogen shift, which would not be structurally formally covered by the formula (I), these tautomers are nevertheless included in the definition of the compounds of the formula (I) according to the invention.
Die Formel (I) umfasst auch alle Stereoisomere der Verbindungen, deren spezifische stereochemische Konfiguration durch die Formel nicht explizit ausgedrückt wird, und deren Gemische. Solche Verbindungen der Formel (I) enthalten ein oder mehrere asymmetrische C-Atome oder auch Doppelbindungen, die in den allgemeinen Formeln (I) nicht gesondert angegeben sind. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von der Formel (I) umfaßt und können nach üblichen Methoden aus Gemischen der Stereoisomere erhalten oder auch durch stereoselektive Reaktionen in Kombination mit dem Einsatz von stereochemisch reinen Ausgangsstoffen hergestellt werden.Formula (I) also includes all stereoisomers of the compounds whose specific stereochemical configuration is not explicitly expressed by the formula, and their mixtures. Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not specified separately in the general formulas (I). The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials are produced.
Die Verbindungen der Formel (I) können durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie beispielsweise HCI, HBr, H2SO oder HNO3, aber auch Oxalsäure oder Sulfonsäuren an eine basische Gruppe, wie z.B. Amino oder Alkylamino, Salze bilden. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salze können ebenfalls dadurch gebildet werden, daß bei geeigneten Substituenten, wie z.B. Sulfonsäuren oder Carbonsäuren, der Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird. Diese Salze sind beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quatemäre) Ammoniumsalze. In der Formel (I) und allen nachfolgenden Formeln gelten folgende Definitionen:The compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, such as, for example, HCl, HBr, H 2 SO or HNO 3 , but also oxalic acid or sulfonic acids, to a basic group, such as, for example, amino or alkylamino. Suitable substituents which are present in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can in turn be protonated, such as amino groups. Salts can also be formed in that, in the case of suitable substituents, such as, for example, sulfonic acids or carboxylic acids, the hydrogen is replaced by a cation which is suitable for agriculture. These salts are, 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 (quaternary) ammonium salts. The following definitions apply in formula (I) and all subsequent formulas:
Ein Kohlenwasserstoffrest ist ein aliphatischer, cycloaliphatischer oder aromatischer monocyclischer oder, im Falle eines gegebenenfalls substituierten Kohlenwasserstoffrestes, auch bicyclischen oder polycyclischen organischen Restes auf Basis der Elemente Kohlenstoff und Wasserstoff, beispielsweise umfassend die Reste Alkyl, Alkenyl, Alkynyl, Cycloalkyl, Cycloalkenyl, Aryl, Phenyl, Naphthyl, Indanyl, Indenyl, etc.; Entsprechendes gilt für die Kohlenwasserstoffoxyreste. Wenn nicht näher definiert, weisen die Kohlenwasserstoff- und Kohlenwasserstoffoxyreste in den obigen Definitionen vorzugsweise 1 bis 20 C- Atome, weiter bevorzugt 1 bis 16 C-Atome, insbesondere 1 bis 12 C-Atome auf.A hydrocarbon radical is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, for example comprising the radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl , Naphthyl, indanyl, indenyl, etc .; The same applies to the hydrocarbonoxy radicals. If not defined in more detail, the hydrocarbon and hydrocarbonoxy radicals in the above definitions preferably have 1 to 20 C atoms, more preferably 1 to 16 C atoms, in particular 1 to 12 C atoms.
Die Kohlenwasserstoffreste und die spezielleren Reste Alkyl, Alkoxy, Haloalkyl, Haloalkoxy, Alkylamino und Alkylthio sowie die entsprechenden ungesättigten und/oder substituierten Reste können im Kohlenstoffgerüst jeweils geradkettig oder verzweigt sein.The hydrocarbon radicals and the more specific radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio as well as the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton.
Der Ausdruck "(Cι-C )Alkyl" bedeutet eine Kurzschreibweise für offenkettiges Alkyl mit einem bis 4 Kohlenstoffatomen, 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. "(Cι-C6)Alkyl" umfassen entsprechend auch gradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. 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 Bedeutungen 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, Heptyle, wie n-Heptyl, 1-Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste; Alkenyl bedeutet z.B. Vinyl, Allyl, 1-Methyl-2- propenyl, 2-Methyl-2-propenyl, 2-Butenyl, Pentenyl, 2-Methylpentenyl oder Hexenyl, vorzugsweise Allyl, 1-Methylprop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, 1-Methyl-but-3-en-1-yl oder 1-Methyl-but-2-en-1-yl. (C2-C6)-Alkynyl bedeutet beispielsweise Ethinyl, Propargyl, 1-Methyl-2-propinyl, 2-Methyl-2-propinyl, 2-ButinyI, 2-Pentinyl oder 2-Hexinyl, vorzugsweise Propargyl, But-2-in-1-yl, But-3-in-1-yl oder 1-Methyl-but-3-in-1-yl.The term "(-C-C) alkyl" means a shorthand notation for open-chain alkyl having one to 4 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-C 6 ) alkyl" 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. Unless specifically stated, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or unsaturated groups having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; Alkenyl means, for example, vinyl, allyl, 1-methyl-2- propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl, preferably allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl , But-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl or 1-methyl-but-2-en-1-yl. (C 2 -C 6 ) -alkynyl means, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2- in-1-yl, but-3-in-1-yl or 1-methyl-but-3-in-1-yl.
Alkyliden, z. B. auch in der Form (CrGioJAIkyliden, bedeutet den Rest eines geradkettigen oder verzweigten Alkans, der über eine Zweifachbindung gebunden ist, wobei die Position der Bindungsstelle noch nicht festgelegt ist. Im Falle eines verzweigten Alkans kommen naturgemäß nur Positionen 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.Alkylidene, e.g. B. also in the form (CrGioJAIkyliden means the remainder of a straight-chain or branched alkane, which is bonded via a double bond, the position of the binding site has not yet been determined. In the case of a branched alkane, only positions in which two H atoms can be replaced by the double bond; residues are e.g. = 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 .
Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Im Falle von substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfaßt, wie beispielsweise Bicyclo[1.1.0]butan-1-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-1-yl, Bicyclo[2.1.0]pentan-2-yl, BicycIo[2.1.0]pentan-5-yl, Adamantan-1-yl und Adamantan-2-yl.Cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the case of substituted cycloalkyl, cyclic systems with substituents are included, substituents also having a double bond on the cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included. In the case of substituted cycloalkyl, multi-cyclic 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 [2.1.0] pentan-2-yl, BicyclIo [2.1.0] pentan-5-yl, adamantan-1-yl and adamantan-2-yl.
Cycloalkenyl bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 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. Im Falle von substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend.Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C 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. In the case of substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.
Halogen bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Haloalkyl, -alkenyl und -alkiήyl bedeuten durch gleiche oder verschiedene Halogenatome, vorzugsweise aus der Gruppe Fluor, Chlor und Brom, insbesondere aus der Gruppe Fluor und Chlor, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl), Perhaloalkyl, CF3, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCI2, CH2CH2CI; Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 und OCH2CH2CI; Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierte Reste.Halogen means, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, alkenyl and -Alkyl mean by the same or different halogen atoms, preferably from the group fluorine, chlorine and bromine, in particular from the group fluorine and chlorine, partially or completely substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohalogenalkyl), perhaloalkyl, CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCI, CCI3, CHCI2, CH2CH2CI; Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF2O, OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
Aryl bedeutet ein mono-, bi- oder polycyclisches aromatisches System, beispielsweise Phenyl, Naphthyl, Tetrahydronaphthyl, Indenyl, Indanyl, Pentalenyl, Fluorenyl und ähnliches, vorzugsweise Phenyl.Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
Ein heterocyclischer Rest oder Ring (Heterocyclyl) kann gesättigt, ungesättigt oder heteroaromatisch sein; wenn nicht anders definiert, enthält er vorzugsweise ein oder mehrere, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S; vorzugsweise ist er ein aliphatischer Heterocyclylrest mit 3 bis 7 Ringatomen oder ein heteroaromatischer Rest mit 5 oder 6 Ringatomen. Der heterocyclische Rest kann z.B. ein heteroaromatischer Rest oder Ring (Heteroaryl) sein, wie z.B. ein mono-, bi- oder polycyclisches aromatisches System, in dem mindestens 1 Ring ein oder mehrere Heteroatome enthält. Vorzugsweise ist er ein heteroaromatischer Ring mit einem Heteroatom aus der Gruppe N, O und S, beispielsweise Pyridyl, Pyrrolyl, Thienyl oder Furyl; weiterhin bevorzugt ist er ein entsprechender heteroaromatischer Ring mit 2 oder 3 Heteroatomen, z. B. Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Imidazolyl und Triazolyl. Weiterhin bevorzugt ist er ein partiell oder vollständig hydrierter heterocyclischer Rest mit einem Heteroatom aus der Gruppe N, O und S, beispielsweise Oxiranyl, Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Oxanyl, Pyrrolinyl, Pyrrolidyl oder Piperidyl.A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; unless otherwise defined, it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S; it is preferably an aliphatic heterocyclyl radical with 3 to 7 ring atoms or a heteroaromatic radical with 5 or 6 ring atoms. The heterocyclic residue can e.g. be a heteroaromatic residue or ring (heteroaryl), e.g. a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms. It is preferably a heteroaromatic ring with a heteroatom from the group N, O and S, for example pyridyl, pyrrolyl, thienyl or furyl; furthermore it is preferably a corresponding heteroaromatic ring with 2 or 3 heteroatoms, e.g. B. pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl and triazolyl. It is furthermore preferably a partially or completely hydrogenated heterocyclic radical having a hetero atom from the group N, O and S, for example oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.
Weiterhin bevorzugt ist er ein partiell oder vollständig hydrierter heterocyclischer Rest mit 2 Heteroatom aus der Gruppe N, O und S, beispielsweise Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl und Morpholinyl. Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten.It is furthermore preferably a partially or completely hydrogenated heterocyclic radical having 2 heteroatoms from the group N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S.
Bevorzugte Beispiele für Heterocyclyl sind ein heterocyclischer Rest mit 3 bis 6 Ringatomen aus der Gruppe Pyridyl, Thienyl, Furyl, Pyrrolyl, Oxiranyl, 2-Oxetanyl, 3- Oxetanyl, Oxolanyl (= Tetrahydrofuryl), Pyrrolidyl, Piperidyl, insbesondere Oxiranyl, 2-Oxetanyl, 3-Oxetanyl oder Oxolanyl, oder ist ein heterocyclischer Rest mit zwei oder drei Heteroatomen, beispielsweise Pyrimidinyl, Pyridazinyl, Pyrazinyl, Triazinyl, Thienyl, Thiazolyl, Thiadiazolyl, Oxazolyl, Isoxazolyl, Pyrazolyl, Triazolyl, Piperazinyl, Dioxolanyl, Oxazolinyl, Isoxazolinyl, Oxazolidinyl, Isoxazolidinyl oder Morpholinyl.Preferred examples of heterocyclyl are a heterocyclic radical with 3 to 6 ring atoms from the group pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (= tetrahydrofuryl), pyrrolidyl, piperidyl, in particular oxiranyl, 2-oxetanyl , 3-oxetanyl or oxolanyl, or is a heterocyclic radical with two or three heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, piperazinyl, oxazazinyl, dioxolinyl, dioxolinyl, dioxolinyl, dioxolinyl, dioxolanyl , Isoxazolidinyl or morpholinyl.
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein.If a basic body is substituted “by one or more residues” from an enumeration of residues (= group) or a generically defined group of residues, this includes the simultaneous substitution by several identical and / or structurally different residues.
Substituierte Reste, wie ein substituierter Alkyl-, Alkenyl-, Alkinyl-, Aryl-, Phenyl-, Benzyl-, Heterocyclyl- und Heteroarylrest, bedeuten beispielsweise einen vom unsubstituierten Grundkörper abgeleiteten substituierten Rest, wobei die Substituenten beispielsweise einen oder mehrere, vorzugsweise 1 , 2 oder 3 Reste aus der Gruppe Halogen, Alkoxy, Alkylthio, Hydroxy, Amino, Nitro, Carboxy, Cyano, Azido, Alkoxycarbonyl, Alkylcarbonyl, Formyl, Carbamoyl, Mono- und Dialkylaminocarbonyl, substituiertes Amino, wie Acylamino, Mono- und Dialkylamino, und Alkylsulfinyl, Alkylsulfonyl und, im Falle cyclischer Reste, auch Alkyl, Haloalkyl, Alkylthio-alkyl, Alkoxy-alkyl, gegebenfalls substituiertes Mono- und Dialkyl- aminoalkyl und Hydroxy-alkyl bedeuten; im Begriff "substituierte Reste" wie substituiertes Alkyl etc. sind als Substituenten zusätzlich zu den genannten gesättigten kohlenwasserstoffhaltigen Resten entsprechende ungesättigte aliphatische und aromatische Reste, wie gegebenenfalls substituiertes Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy, Phenyl, Phenoxy etc. eingeschlossen. Im Falle von substituierten cyclischen Resten mit aliphatischen Anteilen im Ring werden auch cyclische Systeme mit solchen Substituenten umfaßt, die mit einer Doppelbindung am Ring gebunden sind, z. B. mit einer Alkylidengruppe wie Methyliden oder Ethyliden oder einer Oxogruppe, Iminogruppe oder substituierten Iminogruppe substituiert sind.Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, mean, for example, a substituted radical derived from the unsubstituted basic body, the substituents for example one or more, preferably 1, 2 or 3 radicals from the group halogen, alkoxy, alkylthio, hydroxy, amino, nitro, carboxy, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and Alkylsulfinyl, alkylsulfonyl and, in the case of cyclic radicals, also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and dialkylaminoalkyl and hydroxyalkyl; in the term "substituted radicals" such as substituted alkyl, etc., as substituents in addition to the saturated hydrocarbon-containing radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, Alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc. included. In the case of substituted cyclic radicals with aliphatic portions in the ring, cyclic systems are also included with those substituents which are bonded to the ring with a double bond, for. B. are substituted with an alkylidene group such as methylidene or ethylidene or an oxo group, imino group or substituted imino group.
Die beispielhaft genannten Substituenten ("erste Substituentenebene") können, sofern sie kohlenwasserstoff haltige Anteile enthalten, dort gegebenenfalls weiter substituiert sein ("zweite Substitutentenebene"), beispielsweise durch einen der Substituenten, wie er für die erste Substituentenebene definiert ist. Entsprechende weitere Substituentenebenen sind möglich. Vorzugsweise werden vom Begriff "substituierter Rest" nur ein oder zwei Substitutentenebenen umfasst.The substituents mentioned by way of example (“first substituent level”) can, if they contain hydrocarbon-containing constituents, be optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level. Corresponding further substituent levels are possible. The term "substituted radical" preferably only includes one or two substituent levels.
Bevorzugte Substituenten für die Substituentenebenen sind beispielsweisePreferred substituents for the substituent levels are, for example
Amino, Hydroxy, Halogen, Nitro, Cyano, Mercapto, Carboxy, Carbonamid, SF5, Aminosulfonyl, Alkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Monoalkyl-amino, Dialkyl-amino, N-Alkanoyl-amino, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkoxy, Cycloalkenyloxy, Alkoxy-carbonyl, Alkenyloxy-carbonyl, Alkinyloxy-carbonyl, Aryloxycarbonyl, Alkanoyl, Alkenyl-carbonyl, Alkinyl-carbonyl, Aryl-carbonyl, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkylsulfonyl, Monoalkyl-aminosulfonyl, Dialkyl-aminosulfonyl, N-Alkyl- aminocarbonyl, N,N-Dialkyl-aminocarbonyl, N-Alkanoyl-amino-carbonyl, N-Alkanoyl- N-alkyl-aminocarbonyl, Aryl, Aryloxy, Benzyl, Benzyloxy, Benzylthio, Arylthio, Arylamino und Benzylamino.Amino, hydroxy, halogen, nitro, cyano, mercapto, carboxy, carbonamide, SF 5 , aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy , Cycloalkoxy, cycloalkenyloxy, alkoxy-carbonyl, alkenyloxy-carbonyl, alkynyloxy-carbonyl, aryloxycarbonyl, alkanoyl, alkenyl-carbonyl, alkynyl-carbonyl, aryl-carbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfonyl, alkylsulfyl , Dialkyl-aminosulfonyl, N-alkyl-aminocarbonyl, N, N-dialkyl-aminocarbonyl, N-alkanoyl-amino-carbonyl, N-alkanoyl-N-alkyl-aminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino and benzylamino.
Bei Resten mit C-Atomen sind solche mit 1 bis 6 C-Atomen, vorzugsweise 1 bis 4 C-Atomen, insbesondere 1 oder 2 C-Atomen bevorzugt. Bevorzugt sind in der Regel Substituenten aus der Gruppe Halogen, z.B. Fluor und Chlor, (Cι-G4)Alkyl, vorzugsweise Methyl oder Ethyl, (CrC )Haloalkyl, vorzugsweise Trifluormethyl, (Cι-C4)Alkoxy, vorzugsweise Methoxy oder Ethoxy, (Cι-C4)Haloalkoxy, Nitro und Cyano. Besonders bevorzugt sind dabei die Substituenten Methyl, Methoxy, Fluor und Chlor.In the case of radicals with carbon atoms, those with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Substituents from the group halogen, for example fluorine and chlorine, (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (CrC) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy or ethoxy, are generally preferred, (Cι-C 4 ) haloalkoxy, nitro and Cyano. The substituents methyl, methoxy, fluorine and chlorine are particularly preferred.
Substituiertes Amino wie mono- oder disubstituiertes Amino bedeutet einen Rest aus der Gruppe der substituierten Aminoreste, welche beispielsweise durch einen bzw. zwei gleiche oder verschiedene Reste aus der Gruppe Alkyl, Alkoxy, Acyl und Aryl N-substituiert sind; vorzugsweise Mono- und Dialkyl-amino, Mono- und Diarylamino, Acylamino, N-Alkyl-N-arylamino, N-Alkyl-N-acylamino sowie N-Heterocyclen; dabei sind Alkylreste mit 1 bis 4 C-Atomen bevorzugt; Aryl ist dabei vorzugsweise Phenyl oder substituiertes Phenyl; für Acyl gilt dabei die weiter unten genannte Definition, vorzugsweise (Cι-C4)Alkanoyl. Entsprechenes gilt für substituiertes Hydroxylamino oder Hydrazino.Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals which are, for example, N-substituted by one or two identical or different radicals from the group alkyl, alkoxy, acyl and aryl; preferably mono- and dialkylamino, mono- and diarylamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred; Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (-C-C 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
Gegebenenfalls substituiertes Phenyl ist vorzugsweise Phenyl, das unsubstituiert oder ein- oder mehrfach, vorzugsweise bis zu dreifach durch gleiche oder verschiedene Reste aus der Gruppe Halogen, (CrC )Alkyl, (C-ι-C )Alkoxy, (Cι-C4)Halogenalkyl, (C-ι-C )Halogenalkoxy und Nitro substituiert ist, z.B. o-, m- und p-Tolyl, Dimethylphenyle, 2-, 3- und 4-Chlorphenyl, 2-, 3- und 4-Trifluor- und -Trichlorphenyl, 2,4-, 3,5-, 2,5- und 2,3-Dichlorphenyl, o-, m- und p-Methoxyphenyl.Optionally substituted phenyl is preferably phenyl which is unsubstituted or one or more times, preferably up to three times, by identical or different radicals from the group halogen, (CrC) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl , (C-ι-C) haloalkoxy and nitro is substituted, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl , 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.
Acyl bedeutet einen Rest einer organischen Säure, der formal durch Abtrennen einer Hydroxygruppe an der Säurefunktion entsteht, wobei der organische Rest in der Säure auch über ein Heteroatom mit der Säurefunktion verbunden sein kann. Beispiele für Acyl sind der Rest -CO-R einer Carbonsäure HO-CO-R und Reste davon abgeleiteter Säuren wie der Thiocarbonsäure, gegebenenfalls N-substituierten Iminocarbonsäuren oder der Rest von Kohlensäuremonoestern, N-substituierter Carbaminsäure, Sulfonsäuren, Sulfinsäuren, N-substituierter Sulfonamidsäuren, Phosphonsäuren, Phosphinsäuren.Acyl means a residue of an organic acid which is formally formed by removing a hydroxyl group on the acid function, the organic residue in the acid also being able to be linked to the acid function via a hetero atom. Examples of acyl are the residue -CO-R of a carboxylic acid HO-CO-R and residues of acids derived therefrom such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the residue of carbonic acid monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamic acids , Phosphonic acids, phosphinic acids.
Acyl bedeutet beispielsweise Formyl, Alkylcarbonyl wie [(Cι-C4)Alkyl]-carbonyl, Phenylcarbonyl, Alkyloxycarbonyl, Phenyloxycarbonyl, Benzyloxycarbonyl, Alkylsulfonyl, Alkylsulfinyl, N-Alkyl-1-iminoalkyl und andere Reste von organischen Säuren. Dabei können die Reste jeweils im Alkyl- oder Phenylteil noch weiter substituiert sein, beispielsweise im Alkylteil durch ein oder mehrere Reste aus der Gruppe Halogen, Alkoxy, Phenyl und Phenoxy; Beispiele für Substituenten im Phenylteil sind die bereits weiter oben allgemein für substituiertes Phenyl erwähnten Substituenten.Acyl means, for example, formyl, alkylcarbonyl such as [(-CC 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic Acids. The radicals in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy; Examples of substituents in the phenyl part are the substituents mentioned generally above for substituted phenyl.
Acyl bedeutet vorzugsweise einen Acylrest im engeren Sinne, d. h. einen Rest einer organischen Säure, bei der die Säuregruppe direkt mit dem C-Atom eines organischen Restes verbunden ist, beispielsweise Formyl, Alkylcarbonyl wie Acetyl oder [(CrC )Alkyl]-carbonyl, Phenylcarbonyl, Alkylsulfonyl, Alkylsulfinyl und andere Reste von organischen SäureAcyl preferably means an acyl radical in the narrower sense, i.e. H. an organic acid residue in which the acid group is directly connected to the carbon atom of an organic residue, for example formyl, alkylcarbonyl such as acetyl or [(CrC) alkyl] carbonyl, phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other residues of organic acid
Wenn ein allgemeiner Rest mit "Wasserstoff' definiert ist, bedeutet dies ein Wasserstoffatom.When a general radical is defined as "hydrogen" it means a hydrogen atom.
Mit "yl-Position" eines Restes ist dessen Bindungstelle bezeichnet.The "yl position" of a residue denotes its binding site.
Im Folgenden werden erfindungsgemäß verwendbare Verbindungen der Formel (I) und deren Salze auch kurz als "erfindungsgemäße Verbindungen (I)" bezeichnet.In the following, compounds of formula (I) and their salts which can be used according to the invention are also referred to briefly as "compounds (I) according to the invention".
Vor allem aus den Gründen der höheren kulturpflanzen- oder nutzpflanzenschützenden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der genannten Formel (I) oder deren Salze 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.Compounds according to the invention of the formula (I) mentioned or their salts, in which individual radicals have one of the preferred meanings already mentioned or mentioned below, are of particular interest, above all for the reasons of the higher crop plant or crop plant protective activity, better selectivity and / or better producibility , or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
Von besonderem Interesse ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin R1 eine Nitrilgruppe (-CN) bedeutet. Von besonderem Interesse ist auch die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin R1 einen Rest der Formel -C(=X)-Y-R oder -C(=X)-Het bedeutet, in welcher X einen divalenten Rest der Formel O, S oder NRa oder N-NRaRb bedeutet, wobei Ra und Rb wie unten definiert sind, und/oder Y eine Gruppe der Formel O, S, NRC oder NRc-NRdRe bedeutet, wobeiOf particular interest is the use according to the invention of compounds of the formula (I) or their salts, in which R 1 denotes a nitrile group (-CN). Also of particular interest is the use according to the invention of compounds of the formula (I) or their salts, in which R 1 is a radical of the formula —C (= X) -YR or —C (= X) -Het, in which X is a divalent Radical of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, and / or Y is a group of the formula O, S, NR C or NR c -NR d R e means where
Rc, Rd und Re wie unten definiert sind, und/oder R Wasserstoff, (C Cι8)Alkyl, (C2-C18)Alkenyl, (C2-C18)Alkinyl,R c , R d and R e are as defined below, and / or R is hydrogen, (C 8 -C 8 ) alkyl, (C 2 -C 18 ) alkenyl, (C 2 -C 18 ) alkynyl,
(C3-C9)CycloalkyI, (C5-C9)Cycloalkenyl, (C3-C9)CycIoalkyl-(Cι-Cι2)alkyl, Phenyl, Phenyl-(Cι-Cι2)alkyI, Heterocyclyl oder Heterocyclyl- (d-C12)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (CrC )AIkoxy, (C-t- C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)HaloaIkenyloxy, (Cr C4)Alkylthio, (C C4)Alkylsulfinyl, (Cι-C4)AIkylsulfonyl, (d- C )HaloalkyIsulfinyI, (Cι-C4)Haloalkylsulfonyl, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (CrC )Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C )Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C )alkylamino]-carbonyl, Di[(Cι-C4)aIkyIamino]- carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder (d-C6)Alkanoyl, (Cι-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl-(Cι-C4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(d-G4)alkylamino]-carbonyl, (Ci-dJAlkylsuIfinyl, (d- C )Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl oder (CrC )HaloalkylsuIfonyl bedeutet und inklusive Substituenten 1 bis 30 C-Atome, vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 16 C-atome aufweist, und/oder(C 3 -C 9 ) cycloalkyI, (C 5 -C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (Cι-Cι 2 ) alkyl, phenyl, phenyl- (Cι-Cι 2 ) alkyI, heterocyclyl or heterocyclyl - (dC 12 ) alkyl, where each of the last 10 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (CrC) alkoxy, (Ct-C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (Cr C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, (d- C) haloalkyIsulfinyI, (Cι-C 4 ) Haloalkylsulfonyl, mono (-C-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (CrC) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C) Haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C) alkylamino] carbonyl, di [(Cι-C 4 ) aIkyIamino] - carbonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (Cι-C 4 ) Haloalkyl is substituted, or (dC 6 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(CC 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [P henyl- (-C-C 4 ) alkyl] -carbonyl, [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, each of the last 4 radicals in the phenyl ring being unsubstituted or substituted, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(dG 4 ) alkylamino] carbonyl, (Ci-dJAlkylsuIfinyl, (d- C) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfinyl or (CrC) HaloalkylsuIfonyl means and including substituents 1 to 30 carbon atoms , preferably Has 1 to 20 carbon atoms, in particular 1 to 16 carbon atoms, and / or
Het einen aliphatischen N-Heterocyclus mit insgesamt 1 bis 3Het an aliphatic N-heterocycle with a total of 1 to 3
Heteroringatomen und insgesamt 5 oder 6 Ringatomen, der mit einem N-Heteroringatom an die Gruppe C(=X) gebunden ist und der als Heteroringatome neben dem N-Atom in der yl-Position noch Heteroatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (d-G4)Alkyl, (d-C4)Alkoxy, (d- d)Haloalkyl, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio und Oxo substituiert ist, bedeutet, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und unabhängig vom Rest R wie für R definiert ist oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, bedeutet, und/oder R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, SCN, CN, (d-Hetero ring atoms and a total of 5 or 6 ring atoms, which is bonded to the group C (= X) with an N hetero ring atom and which can also contain hetero atoms from the group N, O and S in addition to the N atom in the yl position as hetero ring atoms and the unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (dG 4 ) alkyl, (dC 4 ) alkoxy, (d- d) haloalkyl, (Cι-C 4 ) haloalkoxy, (dC 4 ) alkylthio and oxo is substituted, where each of the radicals R a , R b , R c , R d and R e in the radicals X and Y is each independently and independently of the radical R as defined for R or a radical of the formula - OR *, where R * is independent of R as defined for R, and / or R 2 and R 6 , each independently of one another, is hydrogen, halogen, SCN, CN, (d-
C4)Alkyl, (C2-C )Alkenyl, (C2-C4)Alkinyl oder (C3-C6)Cycloalkyl, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (d-C4)Haloalkoxy, (Cι-C )Alkylthio, (Cι-C4)Alkylsulfinyl, (d-C4)AlkylsulfonyI, (C C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (d-C )Haloalkanoyl, [(d-dJAlkoxyjcarbonyl, [(CrC4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(d-C4)alkylamino]- carbonyl, Di[(CrC4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (d-dJAlkyl und (d-dJHaloalkyl substituiert ist, bedeuten und/oder R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oderC 4 ) alkyl, (C 2 -C) alkenyl, (C 2 -C 4 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy , Amino, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (Cι-C) alkylthio, (Cι-C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyI, (CC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (dC) haloalkanoyl, [(d-dJalkoxyjcarbonyl, [(CrC 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(dC 4 ) alkylamino] carbonyl, di [(CrC 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (d-dJalkyl and (d-dJhaloalkyl) is substituted, and / or R 3 ( a) in the case n = 0, a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or
(b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder (b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oder (b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, Wasserstoff, (d-C18)Alkyl, (C2-Cι8)Alkenyl, (C2-C18)Alkinyl, (C3-C9)CycIoalkyl, (C5-C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(Cι-d2)alkyl, Phenyl, Phenyl- (Cι-Cι2)alkyl, Heterocyclyl oder Heterocyclyl-(CrC12)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (d-C )Alkoxy, (Cι-C4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C4)HaloaIkenyloxy, (C1-C4)Alkylthio, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (Cι-C4)HaloaIkylsulfinyl, (d- C4)HaloalkyIsulfonyl, Mono(d-C )alkylamino, Di(d-C4)alkylamino, (d-C4)Alkanoyl, (C1-C4)Haloalkanoyl, [(Cι-C )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C )alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, bedeutet und inklusive Substituenten 1 bis 30 C-Atome, vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 16 C-atome aufweist, und/oder wobei jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, (Cι-C6)Alkanoyl, (d-C )Haloalkanoyl, [(CrC )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(d-C )alkylamino]- carbonyl, (Cι-C4)Alkylsulfinyl, (Cι-C4)AlkylsuIfonyl, (Cι-C4)Haloalkylsulfinyl oder (Cι-C4)Haloalkylsulfonyl bedeutet und/oder wobei jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen einen aliphatischen oder aromatischen Heterocyclus mit insgesamt 1 bis 3 Heteroringatomen aus der Gruppe N, O und S und insgesamt 5 oder 6 Ringatomen, und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (Cι-C )Alkyl, (d-C )AIkoxy, (d- C4)Haloalkyl, (Cι-C4)Haloalkoxy, (d-dJAlkyllhio und Oxo substituiert ist, bedeutet und/oder Z, Z', Z", jeweils unabhängig voneinander, eine Gruppe der Formel O, S(O)x oder NR\ wobei x = 0, 1 oder 2 ist und R' Wasserstoff, (d-dJAlkyl, (C2-C4)Alkenyl, (C2- C4)Alkinyl, (C3-C6)Cycloalkyl, (C1-C4)Alkoxy, (C2-C4)AIkenyloxy, (C2- C )Alkinyloxy oder (C3-C6)Cycloalkyloxy, wobei jeder der letztgenannten 8 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (d-C4)HaloaIkoxy, (d-C4)Alkylthio, (Cι-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C )Haloalkylsulfonyl, Mono(Cι-C4)alkylamino, Di(C C4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder (d-C6)Alkanoyl, (d-C4)Haloalkanoyl, (d-C6)Alkanoyloxy, (CrC4)Haloalkanoyloxy, [(d-C4)Alkoxy]carbonyl, [(Cι-C )Haloalkoxy]carbonyl, [(C1-C )Alkoxy]carbonyloxy, [(CrC4)Haloalkoxy]carbonyIoxy, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C )alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Phenylcarbonyloxy, Phenoxycarbonyloxy, [Phenyl-(Cι-C4)alkyl]-carbonyloxy, oder [Phenyl- (Cι-C4)alkoxy]-carbonyloxy, wobei jeder der letztgenannten 8 Reste im Phenylring unsubstituiert oder substituiert ist, oder Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (Ci- C4)Alkylsulfinyi, (C C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (C C4)Haloalkylsulfonyl bedeutet, m eine ganze Zahl 0 oder 1 , n eine ganze Zahl 0 oder 1 und o eine ganze Zahl 0 oder 1 , bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und einem Rest der Formel B1, B2 bzw.(b) in the case of n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case of m = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or (b) in the case of m = 1 hydrogen or a radical of the formula A 2 , B 2 or C 2 and (a) in the case o = 0 hydrogen or a radical of the formula A 3 or B 3 or (b) in the case o = 1 is hydrogen or a radical of the formula A 3 , B 3 or C 3 , each of the radicals A 1 , A 2 , A 3 , in each case independently of one another, hydrogen, (dC 18 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 18 ) alkynyl, (C 3 -C 9 ) cycloalkyl, (C 5 -C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (Cι-d 2 ) alkyl, phenyl, phenyl- (Cι -Cι 2 ) alkyl, heterocyclyl or heterocyclyl- (CrC 1 2) alkyl, each of the last 10 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (dC) alkoxy, (-C-C 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (C 1 -C 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, ( Cι-C 4 ) Haloalkylsulfinyl, (d- C 4 ) HaloalkyIsulfonyl, mono (dC) alkylamino, di (dC 4 ) alkylamino, (dC 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [ (-C-C) alkoxy] carbonyl, [(-C-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl and in the case of cyclic Residues are also substituted by (C 4 -C 4 ) alkyl and (C 1 -C 4 ) haloalkyl, and have and including substituents 1 to 30 C atoms, preferably 1 to 20 C atoms, in particular 1 to 16 C atoms, and / or wherein each of the radicals B 1 , B 2 , B 3 , in each case independently of one another, (-C-C 6 ) alkanoyl, (dC) haloalkanoyl, [(CrC) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, Phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) alkyl] -carbonyl, [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, each of the latter 4 radicals in the phenyl ring being unsubstituted or substituted, aminocarbonyl, mono [( Cι-C4) alkylamino] carbonyl, di [(dC) alkylamino] - carbonyl, (Cι-C4) alkylsulfinyl, (Cι-C 4) AlkylsuIfonyl, (Cι-C4) haloalkylsulfinyl or (Cι-C 4) haloalkylsulfonyl means and / or wherein each of the radicals C 1, C 2, C 3 each independently separately of each other, a is an aliphatic or aromatic heterocycle having a total of 1 to 3 Hetero ring atoms from the group N, O and S and a total of 5 or 6 ring atoms, and which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (-C-C) alkyl, (dC) alkoxy, (d- C 4 ) Haloalkyl, (-C-C 4 ) haloalkoxy, (d-dJAlkyllhio and oxo is substituted, means and / or Z, Z ', Z ", in each case independently of one another, a group of the formula O, S (O) x or NR \ where x = 0, 1 or 2 and R 'is hydrogen, (d-dJalkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 - C) alkynyloxy or (C 3 -C 6 ) cycloalkyloxy, each of the latter 8 residues being unsubstituted or by one or more residues from the group halogen, Hydroxy, amino, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (Cι-C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C) Haloalkylsulfonyl, mono (-C-C 4 ) alkylamino, di (CC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (Cι-C 4 ) halo alkanoyl, [(CC 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl and in the case Cyclic radicals are also substituted by (-C 4 ) alkyl and (dC 4 ) haloalkyl, or (dC 6 ) alkanoyl, (dC 4 ) haloalkanoyl, (dC 6 ) alkanoyloxy, (CrC 4 ) haloalkanoyloxy, [(dC 4 ) alkoxy ] carbonyl, [(Cι-C) haloalkoxy] carbonyl, [(C 1 -C) alkoxy] carbonyloxy, [(CrC 4 ) haloalkoxy] carbonyloxy, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C) alkyl] -carbonyl, [Phenyl- (CrC 4 ) alkoxy] -carbonyl, phenylcarbonyloxy, phenoxycarbonyloxy, [phenyl- (Cι-C 4 ) alkyl] -carbonyloxy, or [Phenyl- (Cι-C 4 ) alkoxy] -carbonyloxy, each of the latter 8 Residues in the phenyl ring is unsubstituted or substituted, or aminocarbonyl, mono [(-C-C 4 ) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl, (Ci-C 4 ) alkylsulfinyi, (CC 4 ) alkylsulfonyl , (dC 4 ) haloalkylsulfinyl or (CC 4 ) haloalkylsulfonyl, m is an integer 0 or 1, n is an integer 0 or 1 and o is an integer 0 or 1, where the sum m + n + o is an integer 1, 2 or 3 and, in the case of the alternatives (b) defined above, at least one of the radicals R. 3 , R 4 and R 5 from radicals from the group consisting of hydrogen and a radical of the formula B 1 , B 2 or
B3 ausgewählt ist.B 3 is selected.
Von besonderem Interesse ist auch die erfindungsgemäße Verwendung vonOf particular interest is the use of
Verbindungen der Formel (I) oder deren Salzen, worinCompounds of formula (I) or their salts, wherein
R1 einen Rest der Formel -C(=X)-Y-R oder -C(=X)-Het bedeutet, in welcherR 1 represents a radical of the formula -C (= X) -YR or -C (= X) -Het, in which
X einen divalenten Rest der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind,X is a divalent radical of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below,
Y eine Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind,Y is a group of the formula O, S, NR C or NR c -NR d R e , where R c , R d and R e are as defined below,
R Wasserstoff, (Cι-C 2)Alkyl, (C2-Cι2)Alkenyl, (C2-Cι2)Alkinyl, (C3-C6)CycIoalkyl, (C5-C6)Cycloalkenyl, (C3-C6)Cycloalkyl-(d-C4)alkyl, Phenyl, Phenyl- (Cι-C )alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkoxy, (Cι-C4)HaloaIkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d- C4)Alkylthio, (C C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (Cι-C4)HaloalkylsuIfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (C C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(d-C )alkylamino]- carbonyl, Di[(Cι-C )alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, oderR is hydrogen, (C 1 -C 2 ) alkyl, (C 2 -C 2 ) alkenyl, (C 2 -C 2 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) Cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (Cι-C) alkyl, heterocyclyl or heterocyclyl- (Cι-C 4 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the Halogen, hydroxy group, (-C-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (d- C 4 ) alkylthio, (CC 4 ) Alkylsulfinyl, (dC 4 ) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfinyl, (Cι-C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (Cι-C 4 ) alkanoyl, ( CC 4 ) haloalkanoyl, [(-C-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(dC) alkylamino] carbonyl, di [(Cι-C) alkylamino] carbonyl and in the case of cyclic radicals also (-CC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, or
(C C4)Alkanoyl, (d-C )Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (CrC4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(d-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl und/oder Het den Rest eines aliphatischen N-Heterocyclus aus der Gruppe Piperazinyl, Piperidinyl, Oxazolidinyl, Isoxazolidinyl und Morpholinyl, der jeweils über das N-Ringatom gebunden ist und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (CrC4)Alkyl, (d- C4)Alkoxy, (Cι-C4)Haloalkyl, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio und Oxo substituiert ist, bedeuten, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und vom Rest R wie für R definiert ist oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, bedeutet.(CC 4 ) alkanoyl, (dC) haloalkanoyl, [(-C-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (CrC 4 ) alkyl] -carbonyl, [ Phenyl- (-C-C 4 ) alkoxy] carbonyl, aminocarbonyl, Mono [(-C-C 4 ) alkylamino] carbonyl, di [(dC 4 ) alkylamino] carbonyl, (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl or (d- C 4 ) Haloalkylsulfonyl and / or Het the residue of an aliphatic N-heterocycle from the group piperazinyl, piperidinyl, oxazolidinyl, isoxazolidinyl and morpholinyl, which is in each case bound via the N-ring atom and which is unsubstituted or by one or more residues from the group halogen, hydroxy, Amino, (CrC 4 ) alkyl, (d-C 4 ) alkoxy, (-C-C 4 ) haloalkyl, (Cι-C 4 ) haloalkoxy, (dC 4 ) alkylthio and oxo are substituted, where each of the radicals R a , R b , R c , R d and R e in the radicals X and Y each independently and from the radical R as defined for R or a radical of the formula -OR *, where R * is independent of R as defined for R. , means.
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worinPreferred is the use according to the invention of compounds of formula (I) or their salts, in which
R1 einen Rest der Formel -C(=X)-Y-R bedeutet, in welcherR 1 represents a radical of the formula -C (= X) -YR, in which
X einen divalenten Rest der Formel O, S oder NRa oder N-NRaRb, vorzugsweiseX is preferably a divalent radical of the formula O, S or NR a or N-NR a R b
O oder NRa, wobei Ra und Rb wie unten definiert sind, Y eine Gruppe der Formel O, S, NRC oder NRc-NRdRe, vorzugsweise O oderO or NR a , where R a and R b are as defined below, Y is a group of the formula O, S, NR C or NR c -NR d R e , preferably O or
NRC, wobei Rc, Rd und Re wie unten definiert sind, R Wasserstoff, (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl,NR C , where R c , R d and R e are as defined below, R is hydrogen, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl,
(C3-C6)CycloaIkyl-(C1-C4)alkyl) Phenyl, Phenyl-(d-C4)alkyl, Heterocyclyl oder(C 3 -C 6 ) Cycloalkyl- (C 1 -C 4 ) alkyl ) phenyl, phenyl- (dC 4 ) alkyl, heterocyclyl or
Heterocyclyl-(d-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (Cr C4)Haloalkoxy, (C1-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, Mono(d-C4)alkylamino, Di(CrC4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (Cι-C )Alkyl und (Cι-C )Haloalkyl substituiert ist, oder (CrC4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (d-C4)alkyl]-carbonyl, [Phenyl-(C C )alkoxy]-carbonyl, Aminocarbonyl, Mono[(CrC )alkylamino]-carbonyl, Di[(d-C4)aIkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, (CrC4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl bedeuten, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und vom Rest R wie für R definiert ist oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, bedeutet.Heterocyclyl- (dC 4 ) alkyl, where each of the latter 9 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (Cr C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (dC 4 ) alkylamino, di (CrC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy ] carbonyl and in the case of cyclic radicals also (-CC) alkyl and (-CC) haloalkyl is substituted, or (CrC 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (dC 4 ) alkyl] -carbonyl, [Phenyl- (CC) alkoxy] -carbonyl, aminocarbonyl, mono [(CrC) alkylamino] -carbonyl, di [(dC 4 ) aIkylamino] -carbonyl, (d- C 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, (CrC 4 ) Haloalkylsulfinyl or (d-C 4 ) Haloalkylsulfonyl mean, wherein each of the radicals R a , R b , R c , R d and R e in the radicals X and Y each independently and from the radical R as defined for R. is or a radical of the formula -OR *, where R * is independent of R as defined for R.
Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin R1 einen Rest der FormelThe use according to the invention of compounds of the formula (I) or their salts in which R 1 is a radical of the formula is particularly preferred
-CO-OR-CO-OR
-C(=NRa)-OR oder-C (= NR a ) -OR or
-CO-NRcR bedeutet, wobei R, Ra, Rb und Rc wie oben definiert sind;-CO-NR c R, where R, R a , R b and R c are as defined above;
vorzugsweise bedeutet dabeipreferably means
R1 einen Rest der Formel -CO-OR, worinR 1 is a radical of the formula -CO-OR, wherein
R Wasserstoff, (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(Cι-C4)alkyl, Phenyl, Phenyl-(Cι-C4)alkyl, Heterocyclyl oder Heterocyclyl-(d-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkoxy, (d- C4)Haloalkoxy, (d-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, Mono(d-C4)alkylamino, Di(d-C4)alkylamino, (d-dJAlkanoyl, (CrC4)Haloalkanoyl, [(CrC4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, und insbesondereR is hydrogen, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (Cι-C 4 ) alkyl, phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (dC 4 ) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (Cι-C 4 ) Alkoxy, (d- C 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (dC 4 ) alkylamino, di (dC 4 ) alkylamino, (d-dJalkanoyl, (CrC 4 ) Haloalkanoyl, [(CrC 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (-C-C 4 ) haloalkyl is substituted, and in particular
R Wasserstoff, (d-C6)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, oder (C3-C6)CycloaIkyl-(d-C4)alkyl, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (d-R is hydrogen, (dC 6 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, or (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, each of the latter 5 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (d-
C4)Alkylthio und im Falle cyclischer Reste auch (d-C4)AIkyl substituiert ist, bedeutet. Ganz besonders ist dabei R1 ein Rest der FormelC 4 ) alkylthio and in the case of cyclic radicals also (dC 4 ) alkyl is substituted. R 1 is very particularly a radical of the formula
-CO-OH-CO-OH
-CO-O' M+ oder-CO-O ' M + or
-CO-OR, worin-CO-OR, wherein
R (Ci-dJAlkyl bedeutet, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C )AIkoxy und (Cι-C4)Alkylthio substituiert ist, undR (Ci-dJAlkyl means that is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (dC) alkoxy and (-C-C 4 ) alkylthio, and
M+ ein für die Landwirtschaft geeignetes Kation, vorzugsweise ein Kationäquivalent eines Alkalimetalls oder Erdalkalimetalls, insbesondere ein Natriumion oder Kaliumion, oder auch ein gegebenenfalls substituiertes Ammoniumion, vorzugsweise NH4 + oder Ammoniumionen von organischen Aminen oder quartäre (quatemäre) Ammoniumionen, bedeutet.M + is a cation suitable for agriculture, preferably a cation equivalent of an alkali metal or alkaline earth metal, in particular a sodium ion or potassium ion, or also an optionally substituted ammonium ion, preferably NH 4 + or ammonium ions of organic amines or quaternary (quaternary) ammonium ions.
Beispiele für solche Reste sind:Examples of such residues are:
R1 = Carboxyl und Salze davon, Methoxycarbonyl, Ethoxycarbonyl, n-R 1 = carboxyl and salts thereof, methoxycarbonyl, ethoxycarbonyl, n-
Propoxycarbonyl, n-Butoxycarbonyl, Isopropoxycarbonyl, (2-Hydroxy-ethoxy)- carbonyl.Propoxycarbonyl, n-butoxycarbonyl, isopropoxycarbonyl, (2-hydroxy-ethoxy) carbonyl.
Vorzugsweise bedeutet R1 auch einen Rest der FormelR 1 preferably also denotes a radical of the formula
-C(=NRa)-OR, worin-C (= NR a ) -OR, wherein
R und Ra wie oben definiert sind, vorzugsweiseR and R a are as defined above, preferably
R (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl,R (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl,
(C3-C6)CycIoalkyl-(CrC4)aIkyl, Phenyl, Phenyl-(Cι-C4)aIkyl, Heterocyclyl oder(C 3 -C 6 ) CycIoalkyl- (CrC 4 ) aIkyl, phenyl, phenyl- (Cι-C 4 ) aIkyl, heterocyclyl or
Heterocyclyl-(Cι-C4)alkyl , wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (CrC4)Alkoxy, (d- C4)Haloalkoxy, (C C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C1-C )Alkylsulfonyl,Heterocyclyl- (-C-C 4 ) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (CrC 4 ) alkoxy, (d- C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C) alkylsulfonyl,
Mono(Cι-C4)aIkyIamino, Di(d-C4)alkylamino, (Cι-C )Alkanoyl,Mono (Cι-C 4 ) aIkyIamino, di (dC 4 ) alkylamino, (Cι-C) alkanoyl,
(Cι-C4)HaIoalkanoyl, [(CrC4)Alkoxy]carbonyI und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder(-C-C 4 ) HaIoalkanoyl, [(CrC 4 ) alkoxy] carbonyI and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (Cι-C 4 ) haloalkyl is substituted, or
(Cι-C4)AIkanoyl, (Cι-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl,(-C-C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl,
[(CrC )Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl-[(CrC) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl-
(Cι-C4)alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyI, Aminocarbonyl,(-C-C 4 ) alkyl] -carbonyl, [phenyl- (CrC 4 ) alkoxy] -carbonyl, aminocarbonyl,
Mono[(d-C4)alkylamino]-carbonyl, Di[(d-C4)aIkylamino]-carbonyl, (d-Mono [(dC 4 ) alkylamino] carbonyl, di [(dC 4 ) alkylamino] carbonyl, (d-
C4)AlkylsulfinyI, (C1-C4)AlkylsuIfonyl, (C C4)HaloalkylsulfinyI oder (CC 4 ) alkylsulfinyI, (C 1 -C 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyI or (C
C )HaloalkylsuIfonyl bedeutet undC) HaloalkylsuIfonyl means and
Ra Wasserstoff bedeutet oder unabhängig voneinander wie vorstehend der Rest R definiert ist oder vorzugsweiseR a is hydrogen or, independently of one another, as defined above, or preferably the radical R is
(Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)AIkoxy]carbonyl, [(Cι-C4)HaIoalkoxy]carbonyI, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyI, Di[(Cι-C4)alkylamino]-carbonyl, (d- C4)AlkyIsulfinyl, (d-C4)AIkylsulfonyl, (d-C4)HaloalkyIsulfinyl oder (C C4)HaloalkylsuIfonyl bedeutet.(-C-C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyI, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) alkyl] -carbonyl, [phenyl- (CrC 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] -carbonyl, di [(Cι-C 4 ) alkylamino] -carbonyl, (d- C 4 ) AlkyIsulfinyl, (dC 4 ) Alkylsulfonyl, (dC 4 ) HaloalkyIsulfinyl or (CC 4 ) HaloalkylsuIfonyl means.
Beispiele für solche Reste sind:Examples of such residues are:
R1 = Methoxy-acetiminocarbonyl, Ethoxy-acetiminocarbonyl, n-Propoxy- acetiminocarbonyl, Isopropoxy-acetiminocarbonyl, (2-Hydroxy-ethoxy)- acetiminocarbonyl, Acetoxy-iminocarbonyl, Acetoxy-methyliminocarbonyl, Acetoxy-Ethyliminocarbonyl, Acetoxy-acetiminocarbonyl.R 1 = methoxy-acetiminocarbonyl, ethoxy-acetiminocarbonyl, n-propoxy-acetiminocarbonyl, isopropoxy-acetiminocarbonyl, (2-hydroxy-ethoxy) - acetiminocarbonyl, acetoxy-iminocarbonyl, acetoxy-methyliminocarbonyl, acetoxy-ethyliminocarbonyl, acetoxy-acetiminocarbonyl.
Vorzugsweise bedeutet R1 auch einen Rest der Formel -CO-NRcR, worin R und Rc wie oben definiert sind, vorzugsweise R Wasserstoff, (C C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(d-C4)alkyl, Phenyl, Phenyl-(C1-C4)alkyl, Heterocyclyl oder Heterocyclyl-(d-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)AIkoxy, (Cr C4)Haloalkoxy, (C1-C4)AlkyIthio, (Cι-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, Mono(Cι-C )alkylamino, Di(C1-C )alkylamino, (d-C4)Alkanoyl, (C C4)Haloalkanoyl, [(d-dJAlkoxyjcarbonyl und im Falle cyclischer Reste auch (d-dJAlkyl und (CrC4)Haloalkyl substituiert ist, oderR 1 preferably also denotes a radical of the formula -CO-NR c R, in which R and R c are as defined above, preferably R is hydrogen, (CC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or Heterocyclyl- (dC 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (Cr C 4 ) haloalkoxy, (C 1 -C 4 ) alkyIthio, (-C-C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, mono (Cι-C) alkylamino, di (C 1 -C) alkylamino, (dC 4 ) alkanoyl, (C C4) haloalkanoyl, [(d- dJAlkoxyjcarbonyl and in the case of cyclic radicals also (d-dJAlkyl and (CrC 4 ) haloalkyl is substituted, or
(d-C4)Alkanoyl, (Cι-C4)HaIoalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (CrC4)alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(CrC )alkylamino]-carbonyl, (Cr C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl bedeutet und(dC 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (CrC 4 ) alkyl] - carbonyl, [phenyl- (CrC 4 ) alkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(CrC) alkylamino] carbonyl, (Cr C 4 ) alkylsulfinyl, (CC 4 ) Alkylsulfonyl, (CC 4 ) haloalkylsulfinyl or (d-C 4 ) haloalkylsulfonyl means and
Rc Wasserstoff bedeutet oder unabhängig voneinander wie vorstehend der Rest R definiert ist oder vorzugsweiseR c is hydrogen or, independently of one another, as defined above or preferably the radical R is
Rc Wasserstoff, (d-C4)Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy und (Cι-C4)Alkylthio substituiert ist, oderR c is hydrogen, (dC 4 ) alkyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (dC 4 ) alkoxy and (Cι-C 4 ) alkylthio, or
(Cι-C4)Alkanoyl, (d-C4)HaloalkanoyI, [(Cι-C )Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, (Cι-C4)Alkylsulfinyl und (Cι-C4)Alkylsulfonyl oder insbesondere Wasserstoff oder (CrC4)Alkyl bedeutet.(-C-C 4 ) alkanoyl, (dC 4 ) haloalkanoyI, [(Cι-C) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, (Cι-C 4 ) alkylsulfinyl and (Cι-C 4 ) alkylsulfonyl or in particular Is hydrogen or (CrC 4 ) alkyl.
Beispiele für solche Reste sind:Examples of such residues are:
R1 = Aminocarbonyl, N-Methylaminocarbonyl, N-Ethylaminocarbonyl, N-(n-Propyl)- aminocarbonyl, N-Isopropylaminocarbonyl, N-Butylaminocarbonyl, N-(2- Hydroxy-ethyl)-aminocarbonyl, N-Cycopropylaminocarbonyl, N- Acetylaminocarbonyl, N-Propionylaminocarbonyl, N,N- Dimethylaminocarbonyl, N,N-Diethylaminocarbonyl, N-Ethyl-N-methyl- aminocarbonyl, N-Acetyl-N-methylaminocarbonyl.R 1 = aminocarbonyl, N-methylaminocarbonyl, N-ethylaminocarbonyl, N- (n-propyl) aminocarbonyl, N-isopropylaminocarbonyl, N-butylaminocarbonyl, N- (2-hydroxyethyl) aminocarbonyl, N-cycopropylaminocarbonyl, N-acetylaminocarbonyl , N-propionylaminocarbonyl, N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N-ethyl-N-methyl- aminocarbonyl, N-acetyl-N-methylaminocarbonyl.
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worinPreferred is the use according to the invention of compounds of formula (I) or their salts, in which
R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, (Cι-d)Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (C C4)Haloalkoxy, (d-d)AIkyithio, (d-C4)Alkylsulfinyl, (d-G4)AlkylsulfonyI, (Cι-C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, Mono(Cι-C )aIkyIamino, Di(Cι-C4)alkyIamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(C C )Alkoxy]carbonyl, [(Cι-C4)HaIoalkoxy]carbonyl, Aminocarbonyl, Mono[(d-C4)alkylamino]-carbonyl und Di[(CrC4)alkylamino]-carbonyl substituiert ist, vorzugweiseR 2 and R 6 , each independently of the other, hydrogen, halogen, (Cι-d) alkyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, (dC 4 ) alkoxy, (CC 4 ) haloalkoxy, (dd ) AIkyithio, (dC 4 ) alkylsulfinyl, (dG 4 ) alkylsulfonyI, (Cι-C 4 ) haloalkylsulfinyl, (Cι-C 4 ) haloalkylsulfonyl, mono (Cι-C) aIkyIamino, di (Cι-C 4 ) alkyIamino, (Cι -C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(CC) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(dC 4 ) alkylamino] carbonyl and di [(CrC 4 ) alkylamino] carbonyl is substituted, preferably
R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, (Cι-C )AlkyI, (d-C4)Hydroxyalkyl oder (d-C4)Haloalkyl bedeutet.R 2 and R 6 , each independently of one another, are hydrogen, halogen, (-C-C) alkyl, (dC 4 ) hydroxyalkyl or (dC 4 ) haloalkyl.
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worinPreferred is the use according to the invention of compounds of formula (I) or their salts, in which
R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oderR 3 (a) in the case n = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or
(b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder(b) in the case of n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case of m = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or
(b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und R5 (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oder(b) in the case m = 1 hydrogen or a radical of the formula A 2 , B 2 or C 2 and R 5 (a) in the case o = 0 hydrogen or a radical of the formula A 3 or B 3 or
(b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander,(b) in the case o = 1, hydrogen or a radical of the formula A 3 , B 3 or C 3 , where each of the radicals A 1 , A 2 , A 3 , in each case independently of one another,
Wasserstoff, (C C12)Alkyl, (C2-Cι2)Alkenyl, (C2-C12)Alkinyl, (C3-C6)Cycloalkyl,Hydrogen, (CC 12 ) alkyl, (C 2 -C 2 ) alkenyl, (C 2 -C 12 ) alkynyl, (C 3 -C 6 ) cycloalkyl,
(C5-C6)Cycloalkenyl, (C3-C6)Cycloalkyl-(Cι-C4)alkyl, Phenyl, Phenyl-(C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) cycloalkyl- (-C-C 4 ) alkyl, phenyl, phenyl-
(Cι-C4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (d-d)Alkoxy, (d-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2- C4)Haloalkenyloxy, (CrC4)Alkylthio, (Cι-C4)Alkylsulfinyl, (d- C4)AlkylsuIfonyl, (Cι-C )Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, Mono(Cι-C4)aIkylamino, Di(d-C4)alkylamino, (Cι-C4)Alkanoyl, (d-dJHaloalkanoyl, [(Cι-C )AIkoxy]carbonyl,(-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (Cι-C 4 ) alkyl, each of the latter 10 residues being unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (dd) alkoxy, (dC 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 - C 4 ) haloalkenyloxy, (CrC 4 ) alkylthio, (Cι -C 4 ) alkylsulfinyl, (d-C4) alkylsulfonyl, (Cι-C) haloalkylsulfinyl, (Cι-C4) haloalkylsulfonyl, mono (Cι-C 4 ) aIkylamino, di (dC 4 ) alkylamino, (Cι-C 4 ) alkanoyl , (d-dJHaloalkanoyl, [(-C-C) alkoxy] carbonyl,
[(Cι-C4)Haloalkoxy]carbonyI, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(Cι-C )alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Gι-d)Haloalkyl substituiert ist, bedeutet und vorzugsweise jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, Wasserstoff, (d- C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl oder (C3-C6)Cycloalkyl, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (CrC )Alkoxy, (Cr C4)HaloaIkoxy, (d-C4)Alkylthio, (C C )Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Alkanoyl, (C1-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Ci-dJHaloalkyl substituiert ist, bedeutet, und/oder wobei jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, (Cι-C4)Alkanoyl, (Ci-dJHaloalkanoyl, [(d-C4)Alkoxy]carbonyl, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (Cι-C4)HaloalkyIsulfinyl oder (Ci- C4)Haloalkylsulfonyl bedeutet oder vorzugsweise jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, (Cι-C )Alkanoyl, [(Cι-C4)Alkoxy]carbonyl oder (Ci-dJAlkylsulfonyl bedeutet und/oder wobei jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen aliphatischen oder aromatischen Heteröcyclus mit insgesamt 1 bis 3 Heteroringatomen aus der Gruppe N, O und S und insgesamt 5 oder 6 Ringatomen, der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d-C4)Alkyl, (C C4)Alkoxy, (d-C4)Haloalkyl, (C C4)Haloalkoxy, (Cι-C4)AIkylthio und Oxo substituiert ist, bedeutet und/oder Z, Z', Z", jeweils unabhängig voneinander, einen Rest der Formel O, S, SO, SO2 oder NR', in dem R' Wasserstoff, (CrC4)AIkyl, (C3-C6)Cycloalkyl oder (CrC )Alkoxy, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-dJAlkoxy, (Cι-C4)Haloalkoxy, (Cι-C4)Alkylthio und im Falle cyclischer Reste auch (CrC4)Alkyl und (d-C4)HaIoalkyl substituiert ist, oder (Cι-C6)Alkanoyl, (CrC4)Haloalkanoyl, (Cι-C6)AIkanoyloxy, (Cι-C4)HaIoalkanoyloxy, [(Cι-C )Alkoxy]carbonyl, Phenylcarbonyl, [Phenyl- (CrC4)alkyl]-carbonyI oder [Phenyl-(Cι-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 3 Reste im Phenylring unsubstituiert oder substituiert ist, oder (d-C4)Alkylsulfinyl oder (CrC4)Alkylsulfonyl bedeutet, oder vorzugsweise Z, Z', Z", jeweils unabhängig voneinander, einen Rest der Formel O, oder NR', in dem R' Wasserstoff, (C1-C4)Alkyl oder (C3-C6)CycloalkyI, wobei jeder der letztgenannten 2 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (Cι-C4)Alkylthio und im Falle cyclischer Reste auch (Cι-C )Alkyl und (Cι-C )Haloalkyl substituiert ist, oder (Cι-C6)Alkanoyl, (CrC4)Haloalkanoyl oder [(d-C4)Alkoxy]carbonyl bedeutet, und m eine ganze Zahl 0 oder 1 , n eine ganze Zahl 0 oder 1 und o eine ganze Zahl 0 oder 1 , bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und einem Rest der Formel B1, B2 bzw. B3 ausgewählt ist.[(-C-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(-C-C 4 ) alkylamino] carbonyl, di [(Cι-C) alkylamino] carbonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (Gι-d) haloalkyl is substituted, and preferably each of the radicals A 1 , A 2 , A 3 , in each case independently of one another, is hydrogen, (d- C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, (CrC) alkoxy, (Cr C 4 ) haloalkoxy, (dC 4 ) alkylthio, (CC) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (dC 4 ) Alkyl and (Ci-dJHaloalkyl is substituted, means and / or wherein each of the radicals B 1 , B 2 , B 3 , each independently of one another, (-C-C 4 ) alkanoyl, (Ci-dJHaloalkanoyl, [(dC 4 ) alkoxy ] carbonyl, (d-C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (-C-C 4 ) haloalkyisulfinyl or (Ci- C4) haloalkylsulfonyl means or, preferably, each of the radicals B 1, B 2, B 3 in each case independently of one another, means (Cι-C) alkanoyl, [(Cι-C4) alkoxy] carbonyl or (Ci-dJAlkylsulfonyl and / or wherein each of the radicals C 1 , C 2 , C 3 , in each case independently of one another, is an aliphatic or aromatic heterocycle with a total of 1 to 3 hetero ring atoms from the group N, O and S and a total of 5 or 6 ring atoms, which is unsubstituted or by one or more radicals from the group halogen, (dC 4 ) alkyl, (CC 4 ) alkoxy, (dC 4 ) haloalkyl, (CC 4 ) haloalkoxy, (-C-C 4 ) alkylthio and oxo is substituted and / or Z, Z ', Z ", in each case independently of one another, a radical of the formula O, S, SO, SO 2 or NR', in which R 'is hydrogen, (CrC 4 ) alkyl, (C 3 -C 6 ) Cycloalkyl or (CrC) alkoxy, each of the latter 3 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, (d-dJalkoxy, (Cι-C 4 ) haloalkoxy, (Cι-C 4 ) alkylthio and in the case cyclic radicals are also substituted (CrC 4 ) alkyl and (dC 4 ) haloalkyl, or (Cι-C 6 ) alkanoyl, (CrC 4 ) haloalkanoyl, (Cι-C 6 ) alkanoyloxy, (Cι-C 4 ) haloalkanoyloxy, [( Cι-C) alkoxy] carbonyl, phenylcarbonyl, [phenyl- (CrC 4 ) alkyl] -carbonyl or [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, each of the last 3 radicals in the phenyl ring being unsubstituted or substituted, or (dC 4 ) alkylsulfinyl or (CrC 4 ) alkylsulfonyl, or preferably Z, Z ', Z ", in each case independently of one another, is a radical of the formula O, or NR', in which R 'is hydrogen, (C 1 -C 4 ) Alkyl or (C 3 -C 6 ) cycloalkyI, each of the latter named 2 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (Cι-C 4 ) alkylthio and in the case of cyclic residues also (Cι-C) alkyl and ( Cι-C) haloalkyl is substituted, or (Cι-C 6 ) alkanoyl, (CrC 4 ) haloalkanoyl or [(dC 4 ) alkoxy] carbonyl, and m is an integer 0 or 1, n is an integer 0 or 1 and o is an integer 0 or 1, where the sum m + n + o is an integer 1, 2 or 3 and, in the case of the alternatives (b) defined above, at least one of the radicals R 3 , R 4 and R 5 Residues from the group consisting of hydrogen and a radical of the formula B 1 , B 2 or B 3 is selected.
Ganz bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin einer, zwei oder drei der Reste R3(Z)n, R4(Z,)m und R5(Z")0 eine Hydroxygruppe oder eine Acyloxygruppe, z. B. Acetyloxy, bedeutet.The use according to the invention of compounds of the formula (I) or their salts, in which one, two or three of the radicals R 3 (Z) n , R 4 (Z , ) m and R 5 (Z ") 0 denotes a hydroxyl group or an acyloxy group, for example acetyloxy.
Von besonderem Interesse ist die Verwendung von Verbindungen der Formel (la), (Ib), (Ic), (Id) und (le),Of particular interest is the use of compounds of the formula (Ia), (Ib), (Ic), (Id) and (Le),
worin R1 bis R5 die genannte Bedeutung haben und die an den gezeigten Sauerstoffatomen gebundenen Reste R3, R4 bzw. R5 jeweils Wasserstoff oder einen Acylrest gemäß B1, B2 bzw. B3 bedeuten, vorzugsweise mindestens einer der an Sauerstoff gebundenen Reste Wasserstoff bedeuten.wherein R 1 to R 5 have the meaning given and the radicals R 3 , R 4 and R 5 which are bonded to the oxygen atoms shown are each hydrogen or an acyl radical according to B 1 , B 2 or B 3 , preferably at least one of the oxygen bound radicals mean hydrogen.
Beispiele für erfindungsgemäß einzusetzende Verbindungen (I) sind in den untenstehenden Tabellen aufgeführt.Examples of compounds (I) to be used according to the invention are given in the the tables below.
Die Verbindungen der Formel (I) sind teilweise bekannt oder können analog bekannten Verfahren hergestellt werden. Ihre Anwendung als Safener oder Resistenzinduktor in Pflanzen ist bisher nicht bekannt gewesen.Some of the compounds of the formula (I) are known or can be prepared analogously to known processes. Their use as safeners or resistance inducers in plants has so far not been known.
Einige Verbindungen der Formel (I) oder deren Salze (im Folgenden summarisch auch als "erfindungsgemäße Verbindungen (I)" oder "Verbindungen (I)" oder "Safener") bezeichnet sind neu und ebenfalls Gegenstand der Erfindung.Some compounds of the formula (I) or their salts (hereinafter also referred to collectively as "compounds (I) according to the invention" or "compounds (I)" or "safeners") are new and likewise a subject of the invention.
Die Verbindungen der Formel (I) können hergestellt werden, indem man die Hydroxybenzoate und deren Carboxylderivate als Basisverbindungen nach üblichen Methoden derivatisiert, z. B. acyliert oder veräthert.The compounds of formula (I) can be prepared by derivatizing the hydroxybenzoates and their carboxyl derivatives as base compounds by conventional methods, e.g. B. acylated or etherified.
Gegenstand der Erfindung ist auch das Verfahren zum Schützen von Kultur- oder Nutzpflanzen vor phytotoxischen Wirkungen von Agrochemikalien, wie Pestiziden, oder vor Umweltfaktoren, welche Schäden an Pflanzen verursachen, dadurch gekennzeichnet, dass man Verbindungen der Formel (I) oder deren Salze als Safener oder Resistenzinduktoren anwendet, vorzugsweise eine effektive Menge der Verbindungen der Formel (I) oder deren Salzen auf die Pflanzen, Teile der Pflanzen oder Samen oder Saatgut davon appliziert.The invention also relates to the method for protecting crops or useful plants from phytotoxic effects of agrochemicals, such as pesticides, or from environmental factors which cause damage to plants, characterized in that compounds of the formula (I) or their salts are used as safeners or Applies resistance inductors, preferably an effective amount of the compounds of formula (I) or their salts applied to the plants, parts of the plants or seeds or seeds thereof.
Die Safener sind geeignet, zusammen mit Wirkstoffen (Pestiziden) zur selektiven Bekämpfung von Schadorganismen in einer Reihe von Pflanzenkulturen, beispielsweise in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Triticale, Roggen, Reis, Mais, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja. Von besonderem Interesse ist dabei die Anwendung in monokotylen Kulturen wie Getreide (Weizen, Gerste, Roggen, Triticale, Sorghum), inklusive Mais und Reis, und monokotyle Gemüsekulturen, aber auch in dikotylen Kulturen wie beispielsweise Soja, Raps, Baumwolle, Wein, Gemüsepflanzen, Obstpflanzen und Zierpflanzen. Dabei sind auch gegenüber einigen Pestiziden partiell tolerante Mutantenkulturen oder partiell tolerante transgene Kulturen von Interesse, z. B. Maiskulturen, die gegenüber Glufosinate oder Glyphosate resistent ist, oder Sojakulturen, die gegen herbizide Imidazolinone resistent ist. Der besondere Vorteil der neuartig eingesetzten Safener ist jedoch ihre effektive Wirkung in Kulturen, welche normalerweise nicht tolerant gegenüber den genannten Pestiziden sind.The safeners are suitable, together with active ingredients (pesticides) for the selective control of harmful organisms in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, triticale, rye, rice, corn, millet), sugar beet, sugar cane, rape , Cotton and soy. Of particular interest is the use in monocot crops such as cereals (wheat, barley, rye, triticale, sorghum), including maize and rice, and monocot vegetable crops, but also in dicot crops such as soybean, rapeseed, cotton, wine, vegetables, Fruit plants and ornamental plants. Partially tolerant mutant cultures or partially tolerant transgenic cultures of interest are also of interest here, e.g. B. corn crops is resistant to glufosinate or glyphosate, or soybean cultures which is resistant to herbicidal imidazolinones. The particular advantage of the new safeners is their effective action in crops that are normally not tolerant of the pesticides mentioned.
Die erfindungsgemäßen Verbindungen der Formel (I) können zur gemeinsamen Anwendung mit Pestiziden gleichzeitig oder in beliebiger Reihenfolge mit den Wirkstoffen ausgebracht werden und sind dann in der Lage, schädliche Nebenwirkungen dieser Wirkstoffe bei Kulturpflanzen zu reduzieren oder völlig aufzuheben, ohne die Wirksamkeit dieser Wirkstoffe gegen unerwünschte Schadorganismen zu beeinträchtigen oder wesentlich zu reduzieren. Dabei können auch Schädigungen, welche durch die Anwendung mehrerer Pestizide entstehen, z.B. durch mehrere Herbizide oder durch Herbizide in Kombination mit Insektiziden oder Fungiziden, wesentlich reduziert oder völlig aufgehoben werden. Hierdurch kann das Einsatzgebiet herkömmlicher Pestizide ganz erheblich erweitert werden.The compounds of the formula (I) according to the invention can be applied together with the pesticides at the same time or in any order with the active compounds and are then able to reduce or completely eliminate harmful side effects of these active compounds in crop plants, without the effectiveness of these active compounds against undesired ones Harm harmful organisms or significantly reduce them. Damage caused by the use of several pesticides, e.g. by several herbicides or by herbicides in combination with insecticides or fungicides, can be significantly reduced or completely eliminated. This allows the area of application of conventional pesticides to be expanded considerably.
Für den Fall, daß die erfindungsgemäßen Mittel Pestizide enthalten, werden diese Mittel nach entsprechender Verdünnung entweder direkt auf die Anbaufläche, auf die bereits gekeimten Schad- und/oder Nutzpflanzen oder auf die bereits aufgelaufenen Schad- und/oder Nutzpflanzen appliziert. Für den Fall, daß die erfindungsgemäßen Mittel kein Pestizid enthalten, können diese Mittel im sogenannten Tankmix- Verfahren - d.h. unmittelbar vor dem Aufbringen auf die zu behandelnde Fläche erfolgt beim Anwender die Vermischung und Verdünnung der separat käuflichen Produkte (= nutzpflanzenschützendes Mittel und Pestizid) - oder zeitlich vor der Anwendung eines Pestizids, oder zeitlich nach der Anwendung eines Pestizids, oder zur Saatgut-Vorbehandlung, d.h. beispielsweise zur Beizung des Nutzpflanzensaatguts verwendet werden.In the event that the agents according to the invention contain pesticides, these agents are applied after appropriate dilution either directly to the area under cultivation, to the already germinated harmful and / or useful plants or to the already emerged harmful and / or useful plants. In the event that the agents according to the invention do not contain any pesticide, these agents can be used in the so-called tank mix process - i.e. Immediately before application to the surface to be treated, the user mixes and dilutes the separately purchased products (= crop protection agent and pesticide) - or before the application of a pesticide, or after the application of a pesticide, or for seed pretreatment, ie can be used, for example, for dressing the crop seeds.
Die vorteilhaften Wirkungen der erfindungsgemäßen Verbindungen (I) werden beobachtet, wenn man die zusammen mit den Pestiziden im Vorauflauf oder im Nachauflauf einsetzt, beispielsweise bei gleichzeitiger Applikation als Tank-mix oder als Co-formulierung oder bei einer separaten Applikation parallel oder nacheinander (Split-Applikation). Auch ist es möglich die Applikation mehrfach zu wiederholen. Manchmal kann es sinnvoll sein, eine Vorauflaufapplikation mit einer Nachauflaufapplikation zu kombinieren. Meist bietet sich die Anwendung als Nachauflaufapplikation auf die Nutz- oder Kulturpflanze mit gleichzeitiger oder späterer Applikation des Pestizids an. In Frage kommt auch die Anwendung der erfindungsgemäßen Verbindungen (I) bei der Saatgutbeizung, der (Tauch-)Behandlung von Keimpflanzen oder Behandlung von anderem Vermehrungsgut (z. B. Kartoffelknollen).The advantageous effects of the compounds (I) according to the invention are observed if they are used together with the pesticides in the pre-emergence or in the post-emergence, for example with simultaneous application as a tank mix or as a co-formulation or with a separate application in parallel or in succession (split Application). It is also possible to repeat the application several times. Sometimes it can make sense to combine a pre-emergence application with a post-emergence application. Usually, the application is a post-emergence application to the crop or crop with simultaneous or later application of the pesticide. The use of the compounds (I) according to the invention in seed dressing, the (immersion) treatment of seedlings or the treatment of other propagation material (for example potato tubers) is also suitable.
Oftmals werden bei der Anwendung der erfindungsgemäßen Verbindungen (I) in Kombination mit Herbiziden neben der Safenerwirkung auch Wirkungsverstärkungen in der Herbizidwirkung gegenüber Schadpflanzen beobachtet. Weiterhin ist das Wachstum der Nutz- und Kulturpflanzen in vielen Fällen verbessert, und es können die Ernteerträge erhöht werden.When using the compounds (I) according to the invention in combination with herbicides, in addition to the safener action, activity enhancements in the herbicide action against harmful plants are often observed. Furthermore, the growth of crops and crops has improved in many cases, and crop yields can be increased.
Die letztgenannten vorteilhaften Wirkungen werden teilweise auch beobachtet, wenn die Verbindungen (I) ohne zusätzliche Pestizide zur Anwendung kommen, insbesondere wenn sonstige Umweltfaktoren das Pflanzenwachstum beeinträchtigen.The latter advantageous effects are also sometimes observed when the compounds (I) are used without additional pesticides, in particular when other environmental factors impair plant growth.
Die erfindungsgemäßen Mittel können ein oder mehrere Pestizide enthalten. Als Pestizide kommen beispielsweise Herbizide, Insektizide, Fungizide, Akarizide und Nematizide, welche jeweils bei alleiniger Anwendung phytotoxische Schäden an den Kulturpflanzen ergeben würden oder bei denen eine Schädigung wahrscheinlich wäre, in Frage. Von besonderem Interesse sind entsprechende pestizide Wirkstoffe aus den Gruppen der Herbizide, Insektizide, Akarizide, Nematizide und Fungizide, insbesondere Herbizide.The agents according to the invention can contain one or more pesticides. Examples of suitable pesticides are herbicides, insecticides, fungicides, acaricides and nematicides which, if used alone, would result in phytotoxic damage to the crop plants or in which damage would be likely. Corresponding pesticidal active substances from the groups of herbicides, insecticides, acaricides, nematicides and fungicides, in particular herbicides, are of particular interest.
Das Gewichtsverhältnis Safener zu Pestizid kann innerhalb weiter Grenzen variiert werden und liegt in der Regel im Bereich von 1:100 bis 100:1 , vorzugsweise 1:20 bis 20:1 , insbesondere 1 :10 bis 10:1. Das optimale Gewichtsverhältnis Safener zu Pestizid hängt sowohl von dem jeweils eingesetzten Safener und dem jeweiligen Pestizid als auch von der Art der zu schützenden Nutz- oder Kulturpflanze ab. Die erforderliche Aufwandmenge an Safener kann je nach verwendetem Pestizid und Art der zu schützenden Nutzpflanze innerhalb weiter Grenzen variiert werden und liegt in der Regel im Bereich von 0,001 bis 10 kg, vorzugsweise 0,005 bis 5 kg, insbesondere 0,1 bis 1 kg Safener je Hektar.The weight ratio of safener to pesticide can be varied within wide limits and is generally in the range from 1: 100 to 100: 1, preferably 1:20 to 20: 1, in particular 1:10 to 10: 1. The optimal weight ratio of safener to pesticide depends both on the safener used and the particular pesticide as well as on the type of crop or crop to be protected. The required amount of safener can be used depending on the pesticide and type the crop to be protected can be varied within wide limits and is generally in the range from 0.001 to 10 kg, preferably 0.005 to 5 kg, in particular 0.1 to 1 kg of safener per hectare.
Im Falle einer Saatbeizung werden beispielsweise 0,005 bis 20 g Safener pro Kilogramm Saatgut, vorzugsweise 0,01 bis 10 g Safener pro Kilogramm Saatgut, insbesondere 0,05 bis 5 g Safener pro Kilogramm Saatgut eingesetzt.In the case of seed dressing, for example 0.005 to 20 g of safener per kilogram of seed, preferably 0.01 to 10 g of safener per kilogram of seed, in particular 0.05 to 5 g of safener per kg of seed, are used.
Wenn Lösungen von Safener in der Saatbehandlung benutzt werden und das Saatgut oder Keimlinge mit den Lösungen benetzt werden, so liegt die geeignete Konzentration in der Regel im Bereich von 1 bis 10000 ppm, vorzugsweise 100 bis 1000 ppm bezogen auf das Gewicht. Die für eine erfolgreiche Behandlung notwendigen Mengen und Gewichtsverhältnisse können durch einfache Vorversuche ermittelt werden.If solutions from Safener are used in the seed treatment and the seed or seedlings are wetted with the solutions, the suitable concentration is generally in the range from 1 to 10000 ppm, preferably 100 to 1000 ppm, based on the weight. The quantities and weight ratios required for successful treatment can be determined by simple preliminary tests.
Die Safener können in üblicher Weise separat oder zusammen mit den Pestiziden formuliert werden. Gegenstand sind daher auch die nutzpflanzen- oder kulturpflanzenschützenden Mittel.The safeners can be formulated in the customary manner separately or together with the pesticides. The subject is therefore also the crop or crop protection agents.
Insektizide, die allein oder gemeinsam mit Herbiziden Pflanzenschädigungen verursachen können, sind beispielsweise folgende:Insecticides that can cause plant damage alone or together with herbicides include the following:
Organophosphate z.B. Terbufos (Counter®), Fonofos (Dyfonate®), PhorateOrganophosphates e.g. Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate
(Thimet®), Chlorpyriphos (Reldan®), Carbamate, wie Carbofuran (Furadan®),(Thimet ® ), Chlorpyriphos (Reldan ® ), carbamates such as Carbofuran (Furadan ® ),
Pyrethroid-Insektizide, wie Tefluthrin (Force®), Deltamethrin (Decis®) undPyrethroid insecticides such as tefluthrin (Force ® ), deltamethrin (Decis ® ) and
Tralomethrin (Scout®) sowie andere insektizide Mittel mit andersartigemTralomethrin (Scout ® ) and other insecticidal agents with other types
Wirkmechanismus.Mechanism of action.
Herbizide, deren phytotoxische Nebenwirkungen auf Kulturpflanzen mittels Verbindungen der Formel I herabgesetzt werden können, können aus ganz unterschiedlichen Strukturklassen sein und ganz unterschiedliche Wirkungsmechanismen aufweisen. Bevorzugt sind kommerziell erhältliche Herbizide, wie sie beispielsweise im Handbuch "The Pesticide Manual", 13th Edition 2003, The British Crop Protection Council und dem e-Pesticide Manual Version 3 (2003) oder auch im names are also referred to in the "Compβndium of Pesticide Common Names" (abfragbar via Internet) und dort zitierter Literatur beschrieben sind. Die wie folgt beispielhaft genannten Herbizide und Pflanzenwachstumsregulatoren sind jeweils in Form ihres standardisierten Wirkstoffnamens (= "Common name", meist entsprechend der englischer Schreibweise) gemäß der "International Organization for Standardization" (ISO) oder mit dem chemischen Namen oder der Code-Nummer bezeichnet. Beispiele für Wirstoffe, deren phytotoxische Wirkung an Kultur- und Nutzpflanzen durch die erfindungsgemäßen Verbindungen (I) reduziert werden können sind: acetochlor; acifluorfen(-sodium); aclonifen; AKH 7088, i.e. [[[1 -[5-[2-chloro- 4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetic acid and its methyl ester; alachlor; alloxydim(-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid, amitrol; AMS, i.e. ammonium sulfamate; anilofos; asulam; atrazine; azafenidin; azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamid; benazolin(-ethyl); benfluralin; benfuresate; bensulfuron(-methyl); bensulide; bentazone(-sodium); benzfendizone, benzobicyclone; benzofenap; benzofluor; benzoylprop(-ethyl); benzthiazuron; bialaphos (bilanafos); bifenox; bispyribac(- sodium); bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil; butamifos; butenachlor; buthidazole; butralin; butroxydim; butylate; cafenstrole (CH-900); carbetamide; carfentrazone(-ethyl); caloxydim, CDAA, i.e. 2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyl diethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorfenprop, chlorflurenol-methyl; chloridazon; chlorimuron(-ethyl); chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlortoluron, cinidon(- methyl or -ethyl), cinmethylin; cinosulfuron; clethodim; clefoxydim, clodinafop and its ester derivatives (for example clodinafop-propargyl); clomazone; clomeprop; cloprop, cloproxydim; clopyralid; clopyrasulfuron(-methyl); cloransulam(-methyl); cumyluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (for example butyl-ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D; 2,4-DB; dalapon; dazomet, desmedipham; desmetryn; di-allate; dicamba; dichlobenil; dichlorprop(-P); diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl(-ethyl); difenoxuron; difenzoquat; iflufenican; diflufenzopyr; dimefuron; dimepiperate; dimethachlor; dimethametryn; methenamid (SAN-582H); dimethenamid(-P); dimethazone, dimethipin; mexyflam, dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; propetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e. 5-cyano- 1-(1 ,1-dimethylethyI)-N-methyl-1 H-pyrazolβ-4-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (for example ethyl ester, HC-252), ethoxysulfuron, etobenzanid (HW 52); F5231 , i.e. N-[2-chloro-4-fluoro-5-[4-(3- fluoropropyI)-4,5-dihydro-5-oxo-1 H-tetrazol-1-yl]-phenyI]ethanesulfonamide; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide; fenuron; flamprop(-methyl or -isopropyl or -isopropyl-L); flazasulfuron; florasulam; fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; fluazolate, flucarbazone(-sodium); flucetosulfuron, fluchloralin; flufenacet (FOE 5043), flufenpyr, flumetsulam; flumeturon; flumiclorac(-pentyl); flumioxazin (S- 482); flumipropyn; fluometuron; fluorochloridone, fluorodifen; fluoroglycofen(-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); fluproanate, flupyrsulfuron(-methyl, or -sodium); flurenol(-butyl); fluridone; flurochloridone; fluroxypyr(-meptyl); flurprimidol, flurtamone; fluthiacet(-methyl); fluthiamide (also known as flufenacet); fomesafen; foramsulfuron; fosamine; furilazole (MON 13900), furyloxyfen; glufosinate(- ammonium); glyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl) and its esters (for example the methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; HC-252 (diphenylether), hexazinone; mazamethabenz(-methyl); imazamethapyr; imazamox; imazapic, imazapyr; mazaquin and salts such as the ammonium salts; imazethamethapyr; imazethapyr, mazosulfuron; indanofan; iodosulfuron-(methyl)-(sodium), ioxynil; isocarbamid; sopropalin; isoproturon; isouron; isoxaben; isoxachlortole; isoxaflutole; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPA-thioethyl, MCPB; mecoprop(-P); mefenacet; mefluidid; mesosulfuron(-methyl); mesotrione; metam, metamifop, metamitron; metazachlor; methabenzthiazuron; methazole; methoxyphenone; methyldymron; metobenzuron, metobromuron; (S-)metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MK-616; molinate; monalide; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N- (3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT 5950, i.e. N-[3-chloro- 4-(1 -methylethyl)-phenyl]-2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyIoxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazone; oxasulfuron; oxaziclomefone; oxyfluorfen; paraquat; pebulate; pelargonic acid; pendimethalin; penoxulam; pentanochlor, pentoxazone; perfluidone; pethoxamid, phenisopham; phenmedipham; picloram; picolinafen; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron(-methyl); procarbazone(-sodium); procyazine; prodiamine; profluazole, profluralin; proglinazine(-ethyl); prometon; prometryn; propachlor; propanil; propaquizafop; propazine; propham; propisochlor; propoxycarbazone(- sodium), propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraclonil, pyraflufen(-ethyl); pyrazolinate; pyrazon; pyrazosulfuron(-ethyl); pyrazoxyfen; pyribenzoxim; pyributicarb; pyridafol; pyridate; pyriftalid, pyrimidobac(-methyl); pyrithiobac(-sodium) (KIH-2031); pyroxofop and its esters (for example propargyl ester); quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example quizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e. 2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyI]-4,5,6,7- tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e. 2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoic acid and its methyl ester; sulcotrione; sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron(-methyl); sulfosate (ICI-A0224); sulfosulfuron; TCA; tebutam (GCP-5544); tebuthiuron; tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutryn; TFH 450, i.e. N,N-diethyl-3-[(2-ethyl-6- methylphenyl)sulfonyl]-1 H-1 ,2,4-triazole-1 -carboxamide; thenylchlor (NSK-850); thiafluamide; thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thidiazuron, thifensulfuron(-methyl); thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triaziflam; triazofenamide; tribenuron(-methyl); 2,3,6-trichlorobenzoic acid (2,3,6-TBA), triciopyr; tridiphane; trietazine; trifloxysulfuron(-sodium), trifluralin; triflusulfuron and esters (e.g. methyl ester, DPX-66037); trimeturon; tritosulfuron; tsitodef; vernolate; WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1 H- tetrazole; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX- N8189; SC-0774; DOWCO-535; DK-8910; V-53482; PP-600; MBH-001 ; KIH-9201 ; ET-751 ; KIH-6127; KIH-2023 and KIH5996.Herbicides, the phytotoxic side effects on crop plants of which can be reduced by means of compounds of the formula I, can be of very different structural classes and have very different mechanisms of action. Preference is given to commercially available herbicides, as described, for example, in the manual "The Pesticide Manual", 13th Edition 2003, The British Crop Protection Council and the e-Pesticide Manual Version 3 (2003) or also in the names are also referred to in the "Compβndium of Pesticide Common Names" (available on the Internet) and the literature cited there. The herbicides and plant growth regulators exemplified as follows are each designated in the form of their standardized active ingredient name (= "common name", usually in English) according to the "International Organization for Standardization" (ISO) or with the chemical name or code number , Examples of active substances whose phytotoxic effect on crops and crop plants can be reduced by the compounds (I) according to the invention are: acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[[1 - [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl] -2-methoxyethylidenes] amino] oxy] acetic acid and its methyl ester; alachlor; alloxydim (-sodium); ametryn; amicarbazone, amidochlor, amidosulfuron; aminopyralid, amitrol; AMS, ie ammonium sulfamate; anilofos; asulam; atrazine; azafenidin; azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516 H, ie 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamid; benazolin (-ethyl); benfluralin; benfuresate; bensulfuron (-methyl); bensulide; bentazone (-sodium); benzfendizone, benzobicyclone; benzofenap; benzofluor; benzoylprop (-ethyl); benzthiazuron; bialaphos (bilanafos); bifenox; bispyribac (- sodium); bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil; butamifos; butenachlor; buthidazole; butraline; butroxydim; butylate; cafenstrole (CH-900); carbetamide; carfentrazone (-ethyl); caloxydim, CDAA, ie 2-chloro-N, N-di-2-propenylacetamide; CDEC, ie 2-chloroallyl diethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorfenprop, chlorflurenol-methyl; chloridazon; chlorimuron (-ethyl); chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron; chlorthal-dimethyl; chlorthiamid; chlorotoluron, cinidon (- methyl or -ethyl), cinmethylin; cinosulfuron; clethodim; clefoxydim, clodinafop and its ester derivatives (for example clodinafop-propargyl); clomazone; clomeprop; cloprop, cloproxydim; clopyralid; clopyrasulfuron (-methyl); cloransulam (-methyl); cumyluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxydim; cycluron; cyhalofop and its ester derivatives (for example butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D; 2,4-DB; dalapon; dazomet, desmedipham; Desmetryn; di-allate; dicamba; dichlobenil; dichlorprop (-P); diclofop and its esters such as diclofop-methyl; diclosulam, diethatyl (ethyl); difenoxuron; difenzoquat; iflufenican; diflufenzopyr; dimefuron; dimepiperate; dimethachlor; dimethametryn; methenamide (SAN-582H); dimethenamid (-P); dimethazone, dimethipin; mexyflam, dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; propetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, ie 5-cyano-1- (1, 1-dimethylethyl) -N-methyl-1 H -pyrazoleβ-4-carboxamide; endothal; epoprodan, EPTC; esprocarb; ethalfluralin; ethametsulfuron-methyl; Ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (for example ethyl ester, HC-252), ethoxysulfuron, etobenzanid (HW 52); F5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyI) -4,5-dihydro-5-oxo-1 H-tetrazol-1-yl] phenyI] ethanesulfonamide; fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; fenoxydim; fentrazamide; fenuron; flamprop (-methyl or -isopropyl or -isopropyl-L); flazasulfuron; florasulam; fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; fluazolate, flucarbazone (sodium); flucetosulfuron, fluchloralin; flufenacet (FOE 5043), flufenpyr, flumetsulam; flumeturon; flumiclorac (-pentyl); flumioxazin (S-482); flumipropyn; fluometuron; fluorochloridones, fluorodifen; fluoroglycofen (-ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); fluproanate, flupyrsulfuron (-methyl, or -sodium); flurenol (-butyl); fluridone; flurochloridone; fluroxypyr (-meptyl); flurprimidol, flurtamone; fluthiacet (-methyl); fluthiamide (also known as flufenacet); fomesafen; foramsulfuron; fosamine; furilazole (MON 13900), furyloxyfen; glufosinate (- ammonium); glyphosate (-isopropylammonium); halo safen; halosulfuron (-methyl) and its esters (for example the methyl ester, NC-319); haloxyfop and its esters; haloxyfop-P (= R-haloxyfop) and its esters; HC-252 (diphenyl ether), hexazinone; mazamethabenz (-methyl); imazamethapyr; imazamox; imazapic, imazapyr; mazaquin and salts such as the ammonium salts; imazethamethapyr; imazethapyr, mazosulfuron; indanofan; iodosulfuron- (methyl) - (sodium), ioxynil; isocarbamid; sopropalin; isoproturon; isouron; isoxaben; isoxachlortole; isoxaflutole; isoxapyrifop; karbutilate; lactofen; lenacil; linuron; MCPA; MCPA thioethyl, MCPB; mecoprop (-P); mefenacet; mefluidide; mesosulfuron (-methyl); mesotrione; metam, metamifop, metamitron; metazachlor; methabenzthiazuron; methazole; methoxyphenone; methyldymron; metobenzuron, metobromuron; (S-) metolachlor; metosulam (XRD 511); metoxuron; metribuzin; metsulfuron-methyl; MK-616; molinate; monalide; monocarbamide dihydrogen sulfates; monolinuron; monuron; MT 128, ie 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazinamine; MT 5950, ie N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; oryzalin; oxadiargyl (RP-020630); oxadiazone; oxasulfuron; oxaziclomefone; oxyfluorfen; paraquat; pebulate; pelargonic acid; pendimethalin; penoxulam; pentanochlor, pentoxazone; perfluidone; pethoxamide, phenisopham; phenmedipham; picloram; picolinafen; piperophos; piributicarb; pirifenop-butyl; pretilachlor; primisulfuron (-methyl); procarbazone (-sodium); procyazine; prodi amines; profluazole, profluralin; proglinazine (-ethyl); prometon; prometryne; propachlor; propanil; propaquizafop; propazine; propham; propisochlor; propoxycarbazone (- sodium), propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prynachlor; pyraclonil, pyraflufen (-ethyl); pyrazolinate; pyrazon; pyrazosulfuron (-ethyl); pyrazoxyfen; pyribenzoxim; pyributicarb; pyridafol; pyridate; pyriftalid, pyrimidobac (methyl); pyrithiobac (sodium) (KIH-2031); pyroxofop and its esters (for example propargyl ester); quinclorac; quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example quizalofop-ethyl; quizalofop-P-tefuryl and ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, ie 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, ie 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and its methyl ester; sulcotrione; sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron (-methyl); sulfosate (ICI-A0224); sulfosulfuron; TCA; tebutam (GCP-5544); tebuthiuron; tepraloxydim; terbacil; terbucarb; terbuchlor; terbumeton; Terbuthylazine; terbutryn; TFH 450, ie N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1 H-1, 2,4-triazole-1-carboxamide; thenylchlor (NSK-850); thiafluamide; thiazafluron; thiazopyr (Mon-13200); thidiazimin (SN-24085); thidiazuron, thifensulfuron (-methyl); thiobencarb; tiocarbazil; tralkoxydim; tri-allate; triasulfuron; triaziflam; triazofenamide; tribenuron (-methyl); 2,3,6-trichlorobenzoic acid (2,3,6-TBA), triciopyr; tridiphane; trietazine; trifloxysulfuron (sodium), trifluralin; triflusulfuron and esters (eg methyl ester, DPX-66037); trimeturon; tritosulfuron; tsitodef; vernolate; WL 110547, ie 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1 H-tetrazole; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; Dowco-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127; KIH-2023 and KIH5996.
Herbizide, deren phytotoxische Nebenwirkungen auf Kulturpflanzen mittels Verbindungen der Formel I herabgesetzt werden können, sind z.B. Herbizide aus der Gruppe der Carbamate, Thiocarbamate, Halogenacetanilide, substituierte Phenoxy-, Naphthoxy- und Phenoxyphenoxycarbonsäure-Derivate sowie Heteroaryloxy- phenoxyalkancarbonsäure-Derivate, wie Chinolyloxy-, Chinoxalyl-oxy-, Pyridyloxy-, Benzoxazolyloxy- und Benzthiazolyloxyphenoxyalkan-carbonsäureester, Cyclo- hexandionoxime, Benzoylcyclohexandione, Benzoylisoxazole, Benzoylpyrazole, Imidazolinone, Pyrimidinyloxy-pyridincarbonsäure-Derivate, Pyrimidyloxy- benzoesäure-Derivate, Sulfonylharnstoffe, Sulfonylaminocarbonyltriazolinone, Triazolo-pyrimidin-sulfonamid-Derivate, Phosphinsäurederivate und deren Salze, Glyzinderivate, Triazolinone, Triazinone sowie S-(N-AryΙ-N-alkylcarbamoylmethyl)- dithiophosphorsäureester, Pyridincarbonsäuren, Pyridine, Pyridincarboxamide, 1 ,3,5-Triazine, und weitere.Herbicides whose phytotoxic side effects on crop plants can be reduced by means of compounds of the formula I are e.g. Herbicides from the group of carbamates, thiocarbamates, haloacetanilides, substituted phenoxy, naphthoxy and phenoxyphenoxycarboxylic acid derivatives as well as heteroaryloxyphenoxyalkanecarboxylic acid derivatives, such as quinolyloxy, quinoxalyloxy, pyridyloxy, benzoxazolyloxycarboxy and benzoxyalkoxy benzoxy , benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles, imidazolinones, pyrimidinyloxy-pyridine carboxylic acid derivatives, pyrimidyloxy benzoic acid derivatives, sulfonylureas, sulphonylaminocarbonyltriazolinones, triazolo-pyrimidine-sulfonamide derivatives, phosphinic acid derivatives and salts thereof, Glyzinderivate, triazolinones, triazinones and S- (N-AryΙ -N-alkylcarbamoylmethyl) - dithiophosphoric acid esters, pyridinecarboxylic acids, pyridines, pyridinecarboxamides, 1, 3,5-triazines, and others.
Bevorzugt sind dabei Phenoxyphenoxy- und Heteroaryloxyphenoxycarbonsäureester und -salze, Cyclohexandionoxime, Benzoylcyclohexandione, Benzoylisoxazole, Sulfonylharnstoffe, Sulfonylaminocarbonyltriazolinone, Imidazolinone sowie Mischungen der genannten Wirkstoffe untereinander und/oder mit Wirkstoffen, die zur Erweiterung des Wirkungsspektrums der Herbizide eingesetzt werden, z.B. Bentazone, Cyanazine, Atrazine, Bromoxynil, Dicamba und andere Blattherbizide.Phenoxyphenoxy- and heteroaryloxyphenoxycarboxylic acid esters and salts, cyclohexanedione oximes, benzoylcyclohexanediones, benzoylisoxazoles, sulfonylureas, sulfonylaminocarbonyltriazolinones, imidazolinones and mixtures of the active ingredients mentioned with one another and / or with active ingredients which are used, for example, to expand the spectrum of active ingredients, are used to broaden the spectrum of active ingredients. Bentazone, Cyanazine, Atrazine, Bromoxynil, Dicamba and other leaf herbicides.
Geeignete Herbizide, die mit den erfindungsgemäßen Safenern kombiniert werden können, sind beispielsweise: A) Herbizide vom Typ der Phenoxyphenoxy- undSuitable herbicides which can be combined with the safeners according to the invention are, for example: A) Herbicides of the phenoxyphenoxy and
Heteroaryloxyphenoxycarbonsäure-Derivate, wieHeteroaryloxyphenoxycarboxylic acid derivatives, such as
A1) Phenoxyphenoxy- und Benzyloxyphenoxy-carbonsäure-Derivate, z.B. 2-(4-A1) Phenoxyphenoxy and benzyloxyphenoxy carboxylic acid derivatives, e.g. 2- (4-
(2,4-Dichlorphenoxy)-phenoxy)-propionsäuremethylester (Diclofop-methyl),(2,4-dichlorophenoxy) phenoxy) propionic acid methyl ester (diclofop-methyl),
2-(4-(4-Brom-2-chlorphenoxy)phenoxy)propionsäuremethylester (DE-A 26 01 548),Methyl 2- (4- (4-bromo-2-chlorophenoxy) phenoxy) propionate (DE-A 26 01 548),
2-(4-(4-Brom-2-fluorphenoxy)phenoxy)propionsäuremethylester (US-A 4,808,750),Methyl 2- (4- (4-bromo-2-fluorophenoxy) phenoxy) propionate (US Pat. No. 4,808,750),
2-(4-(2-Chlor-4-trifluormethylphenoxy)phenoxy)propionsäuremethylester (DE-AMethyl 2- (4- (2-chloro-4-trifluoromethylphenoxy) phenoxy) propionate (DE-A
24 33 067),24 33 067),
2-(4-(2-FIuor-4-trifluormethylphenoxy)phenoxy)propionsäuremethylester (US-AMethyl 2- (4- (2-fluorine-4-trifluoromethylphenoxy) phenoxy) propionate (US-A
4,808,750),4,808,750)
2-(4-(2,4-Dichlorbenzyl)phenoxy)propionsäuremethylester (DE-A 24 17487),Methyl 2- (4- (2,4-dichlorobenzyl) phenoxy) propionate (DE-A 24 17487),
4-(4-(4-Trifluormethylphenoxy)phenoxy)pent-2-en-säureethylester,4- (4- (4-trifluoromethylphenoxy) phenoxy) pent-2-en-oate,
2-(4-(4-Trifluormethylphenoxy)phenoxy)propionsäuremethylester (DE-A 24 33 067);Methyl 2- (4- (4-trifluoromethylphenoxy) phenoxy) propionate (DE-A 24 33 067);
(r?)-2-[4-(4-Cyano-2-fluorphenoxy)phenoxy]propionsäurebutylester (Cyhalofop-butyl)(r?) - 2- [4- (4-Cyano-2-fluorophenoxy) phenoxy] propyl butyl ester (cyhalofop-butyl)
A2) "Einkernige" Heteroaryloxyphenoxy-alkancarbonsäure-Derivate, z.B.A2) "Mononuclear" heteroaryloxyphenoxy alkane carboxylic acid derivatives, e.g.
2-(4-(3,5-Dichlorpyridyl-2-oxy)phenoxy)propionsäureethylester (EP-A 0 002 925),Ethyl 2- (4- (3,5-dichloropyridyl-2-oxy) phenoxy) propionate (EP-A 0 002 925),
2-(4-(3,5-Dichlorpyridyl-2-oxy)phenoxy)propionsäurepropargylester2- (4- (3,5-dichloropyridyl-2-oxy) phenoxy) propionsäurepropargylester
(EP-A 0 003 114),(EP-A 0 003 114),
(RS)- oder (R)-2-(4-(3-Chlor-5-trifluormethyl-2-pyridyIoxy)phenoxy)propionsäure- methylester (Haloxyfop-methyl bzw. Haloxyfop-P-methyl),(RS) - or (R) -2- (4- (3-chloro-5-trifluoromethyl-2-pyridyIoxy) phenoxy) propionic acid methyl ester (haloxyfop-methyl or haloxyfop-P-methyl),
2-(4-(3-Chlor-5-trifluormethyl-2-pyridyloxy)phenoxy)propionsäureethylester2- (4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid ethyl ester
(EP-A 0 003 890),(EP-A 0 003 890),
2-(4-(5-Chlor-3-fluor-2-pyridyloxy)phenoxy)propionsäurepropargylester2- (4- (5-chloro-3-fluoro-2-pyridyloxy) phenoxy) propionsäurepropargylester
(Clodinafop-propargyl),(Clodinafop-propargyl),
(RS)- oder ( ?)-2-(4-(5-Trifluormethyl-2-pyridyloxy)phenoxy)propionsäurebutylester(RS) - or (?) - 2- (4- (5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid butyl ester
(Fluazifop-butyl bzw. Fluazifop-P-butyl);(Fluazifop-butyl or fluazifop-P-butyl);
(R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic acid(R) -2- [4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid
A3) "Zweikernige" Heteroaryloxyphenoxy-alkancarbonsäure-Derivate, z.B. (RS)- oder (f?)-2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäuremethylester und -ethylester (Quizalofop-methyl und -ethyl bzw. Quizalofop-P-methyl und -P-ethyl), 2-(4-(6-Fluor-2-chinoxalyloxy)phenoxy)propionsäuremethylester (s. J. Pest. Sei. Vol. 10, 61 (1985)),A3) "dinuclear" heteroaryloxyphenoxy-alkanecarboxylic acid derivatives, for example (RS) - or (f?) - 2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid methyl ester and -ethyl ester (quizalofop-methyl and -ethyl or quizalofop-P-methyl and -P-ethyl), methyl 2- (4- (6-fluoro-2-quinoxalyloxy) phenoxy) propionate (see J. Pest. Sei. Vol. Vol 10, 61 (1985)),
(R)-2-(4-(6-Chlor-2-chinoxaIyloxy)phenoxy)propionsäure-2-isopropylidenaminooxy- ethylester (Propaquizafop),(R) -2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid 2-isopropylidene aminooxy ethyl ester (propaquizafop),
(RS)- oder (R)-2-(4-(6-Chlorbenzoxazol-2-yl-oxy)phenoxy)propionsäureethylester (Fenoxaprop-ethyl bzw. Fenoxaprop-P-ethyl),(RS) - or (R) -2- (4- (6-chlorobenzoxazol-2-yl-oxy) phenoxy) propionic acid ethyl ester (fenoxaprop-ethyl or fenoxaprop-P-ethyl),
2-(4-(6-Chlorbenzthiazol-2-yloxy)phenoxy)propionsäureethylester (DE-A-26 40 730), (RS)- oder (R)-2-(4-(6-Chlorchinoxalyloxy)phenoxy)propionsäure-tetrahydro-2- furylmethylester (EP-A-0 323 727);2- (4- (6-Chlorobenzthiazol-2-yloxy) phenoxy) propionic acid ethyl ester (DE-A-26 40 730), (RS) - or (R) -2- (4- (6-chloroquinoxalyloxy) phenoxy) propionic acid- tetrahydro-2-furylmethyl ester (EP-A-0 323 727);
B) Herbizide aus der Reihe der Sulfonylharnstoffe, wie Pyrimidin- oderB) herbicides from the series of sulfonylureas, such as pyrimidine or
TriazinylaminocarbonyI-[benzol-, pyridin-, pyrazol-, thiophen- und (alkylsulfonyl)- alkylamino-]-sulfamide. Bevorzugt als Substituenten am Pyrimidinring oderTriazinylaminocarbonyI- [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] sulfamides. Preferred as a substituent on the pyrimidine ring or
Triazinring sind Alkoxy, Alkyl, Haloalkoxy, Haloalkyl, Halogen oder Dimethylamino, wobei alle Substituenten unabhängig voneinander kombinierbar sind. BevorzugteTriazine rings are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, where all substituents can be combined independently of one another. preferred
Substituenten im Benzol-, Pyridin-, Pyrazol-, Thiophen- oder (Alkylsulfonyl)- alkylamino-Teil sind Alkyl, Alkoxy, Halogen, Nitro, Alkoxycarbonyl, Aminocarbonyl,Substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl) alkylamino part are alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkoxyaminocarbonyl, Halogenalkoxy,Alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy,
Halogenalkyl, Alkylcarbonyl, Alkoxyalkyl, (Alkansulfonyl)alkylamino. Solche geeignete Sulfonylharnstoffe sind beispielsweiseHaloalkyl, alkylcarbonyl, alkoxyalkyl, (alkanesulfonyl) alkylamino. Examples of such suitable sulfonylureas are
B1 ) Phenyl- und Benzylsulfonylhamstoffe und verwandte Verbindungen, z.B.B1) phenyl and benzylsulfonyl ureas and related compounds, e.g.
1-(2-Chlorphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)hamstoff1- (2-Chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea
(Chlorsulfuron),(Chlorsulfuron),
1-(2-Ethoxycarbonylphenylsulfonyl)-3-(4-chlor-6-methoxypyrimidin-2-yl)harnstoff1- (2-Ethoxycarbonylphenylsulfonyl) -3- (4-chloro-6-methoxypyrimidine-2-yl) urea
(Chlorimuron-ethyl),(Chlorimuron-ethyl),
1-(2-Methoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)harnstoff1- (2-methoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea
(Metsulfuron-methyl),(Metsulfuron-methyl),
1-(2-Chlorethoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)ham-stoff1- (2-chloroethoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea
(Triasulfuron),(Triasulfuron),
1-(2-Methoxycarbonylphenylsulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)harnstoff1- (2-Methoxycarbonylphenylsulfonyl) -3- (4,6-dimethylpyrimidin-2-yl) urea
(Sulfumeturon-methyl), 1-(2-Methoxycarbonylphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)-3- methylhamstoff (Tribenuron-methyl),(Sulfumeturon-methyl), 1- (2-methoxycarbonylphenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -3-methylurea (tribenuron-methyl),
1-(2-Methoxycarbonylbenzylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)harnstoff1- (2-Methoxycarbonylbenzylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea
(Bensulfuron-methyl),(Bensulfuron-methyl),
1-(2-Methoxycarbonylphenylsulfonyl)-3-(4,6-bis-(difluormethoxy)pyrimidin-2-yl)- hamstoff (Primisulfuron-methyl),1- (2-methoxycarbonylphenylsulfonyl) -3- (4,6-bis- (difluoromethoxy) pyrimidin-2-yl) urea (primisulfuron-methyl),
3-(4-Ethyl-6-methoxy-1 ,3,5-triazin-2-yl)-1-(2,3-dihydro-1 ,1-dioxo-2-methylbenzo-3- (4-ethyl-6-methoxy-1, 3,5-triazin-2-yl) -1- (2,3-dihydro-1, 1-dioxo-2-methylbenzo-
[b]thiophen-7-sulfonyl)hamstoff (EP-A 0 796 83),[b] thiophene-7-sulfonyl) urea (EP-A 0 796 83),
3-(4-Ethoxy-6-ethyl-1 ,3,5-triazin-2-yl)-1 -(2,3-dihydro-1 ,1 -dioxo-2-methylbenzo[b]- thiophen-7-sulfonyl)harnstoff (EP-A 0 079 683),3- (4-Ethoxy-6-ethyl-1,3,5-triazin-2-yl) -1 - (2,3-dihydro-1,1-dioxo-2-methylbenzo [b] thiophene-7- sulfonyl) urea (EP-A 0 079 683),
3-(4-Methoxy-6-methyl-1 ,3,5-triazin-2-yl)-1-(2-methoxycarbonyl-5-jod-phenyl- sulfonyl)-harnstoff (WO 92/13845),3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -1- (2-methoxycarbonyl-5-iodophenylsulfonyl) urea (WO 92/13845),
2-[4-Dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-3- methyl-benzoesäuremethylester (DPX-66037, Triflusulfuron-methyl),2- [4-Dimethylamino-6- (2,2,2-trifluoroethoxy) -1,3,5-triazin-2-ylcarbamoylsulfamoyl] -3-methyl-benzoic acid methyl ester (DPX-66037, triflusulfuron-methyl),
2-[(4,6-dimethylpyrimidin-2-yl)-carbamoylsulfamoyl]benzoesäureoxetan-3-ylester2 - [(4,6-dimethylpyrimidin-2-yl) -carbamoylsulfamoyl] benzoesäureoxetan-3-yl ester
(CGA-277476, Oxasulfuron),(CGA-277476, oxasulfuron),
4-lod-2-[3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)ureidosulfonyl]- benzoesäuremethylester, Natriumsalz (lodosulfuron-methyl-Natrium),4-iodo-2- [3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) ureidosulfonyl] methyl benzoate, sodium salt (iodosulfuron-methyl-sodium),
2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methansulfonylamino-methyl- benzoesäuremethylester (Mesosulfuron-methyl, WO 95/10507),2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-methanesulfonylamino-methylbenzoic acid methyl ester (mesosulfuron-methyl, WO 95/10507),
N,N-Dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-formylamino- benzamid (Foramsulfuron, WO 95/01344),N, N-dimethyl-2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -4-formylamino-benzamide (foramsulfuron, WO 95/01344),
1-(4,6-Dimethoxy-1 ,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenylsulfonyl]harnstoff1- (4,6-Dimethoxy-1, 3,5-triazin-2-yl) -3- [2- (2-methoxyethoxy) phenylsulfonyl] urea
(Cinosulfuron),(Cinosulfuron),
2-[(4-Ethoxy-6-methylamino-1 ,3,5-triazin-2-yl)carbamoylsulfarhoyl]benzoesäure- methylester (Ethametsulfuron-methyl),2 - [(4-ethoxy-6-methylamino-1, 3,5-triazin-2-yl) carbamoylsulfarhoyl] methyl benzoate (ethametsulfuron-methyl),
1-(4-Methoxy-6-methyl-1 ,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]- hamstoff (Prosulfuron),1- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -3- [2- (3,3,3-trifluoropropyl) phenylsulfonyl] urea (prosulfuron),
2-(4,6-Dimethylpyrimidin-2-ylcarbamoylsulfamoyl)benzoesäuremethylester2- (4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl) benzoate
(Sulfometuron-methyl),(Sulfometuron methyl),
1-(4-Methoxy-6-trifluoromethyl-1,3,5-triazin-2-yl)-3-(2-trifluoromethylbenzolsulfonyl)- hamstoff (Tritosulfuron), B2) Thienylsulfonylhamstoffe, z.B.1- (4-methoxy-6-trifluoromethyl-1,3,5-triazin-2-yl) -3- (2-trifluoromethylbenzenesulfonyl) urea (tritosulfuron), B2) Thienylsulfonylureas, e.g.
1-(2-Methoxycarbonylthiophen-3-yl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2- yl)hamstoff (Thifensulfuron-methyl);1- (2-methoxycarbonylthiophene-3-yl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea (thifensulfuron-methyl);
B3) Pyrazolylsulfonylharnstoffe, z.B.B3) pyrazolylsulfonylureas, e.g.
1-(4-Ethoxycarbonyl-1-methylpyrazoI-5-yl-sulfonyl)-3-(4,6-dimethoxypyrimidin-2- yl)harnstoff (Pyrazosulfuron-ethyl),1- (4-ethoxycarbonyl-1-methylpyrazoI-5-yl-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (pyrazosulfuron-ethyl),
3-Chlor-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methyl-pyrazol-4- carbonsäuremethylester (Halosulfuron-methyl),3-chloro-5- (4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -1-methyl-pyrazol-4-carboxylic acid methyl ester (halosulfuron-methyl),
5-(4,6-Dimethylpyrimidin-2-yl-carbamoylsulfamoyl)-1-(2-pyridyl)-pyrazol-4-car- bonsäuremethylester (NC-330, s. Brighton Crop Prot. Conference 'Weeds' 1991 , Vol.5- (4,6-Dimethylpyrimidin-2-yl-carbamoylsulfamoyl) -1- (2-pyridyl) -pyrazole-4-carboxylic acid methyl ester (NC-330, see Brighton Crop Prot. Conference 'Weeds' 1991, vol.
1 , S. 45 ff.),1, p. 45 ff.),
1-(4,6-Dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2 -/-tetrazol-5-yl)pyrazol-5- ylsulfonyljharnstoff (DPX-A8947, Azimsulfuron);1- (4,6-Dimethoxypyrimidin-2-yl) -3- [1-methyl-4- (2-methyl-2 - / - tetrazol-5-yl) pyrazol-5-ylsulfonylurea (DPX-A8947, azimsulfuron) ;
B4) Sulfondiamid-Derivate, z.B.B4) sulfone diamide derivatives, e.g.
3-(4,6-Dimethoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonyIaminosulfonyl)- hamstoff (Amidosulfuron) und dessen Strukturanaloge (EP-A 0 131 258 und Z. Pfl. Krankh. Pfl. Schutz, Sonderheft XII, 489-497 (1990));3- (4,6-Dimethoxypyrimidin-2-yl) -1- (N-methyl-N-methylsulfonyaminosulfonyl) urea (amidosulfuron) and its structural analogues (EP-A 0 131 258 and Z. Pfl. Krankh. Pfl. Schutz , Special Issue XII, 489-497 (1990));
B5) Pyridylsulfonylharnstoffe, z.B.B5) pyridylsulfonylureas, e.g.
1-(3-N,N-Dimethylaminocarbonylpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2- yl)hamstoff (Nicosulfuron),1- (3-N, N-Dimethylaminocarbonylpyridin-2-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (nicosulfuron),
1-(3-Ethylsulfonylpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)harnstoff1- (3-Ethylsulfonylpyridin-2-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea
(Rimsulfuron),(Rimsulfuron),
2-[3-(4,6-Dimethoxypyrimidin-2-yl)ureidosulfonyl]-6-trifluormethyl-3-pyridin- carbonsäuremethylester, Natriumsalz (DPX-KE 459, Flupyrsulfuron-methyl-natrium),2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyl] -6-trifluoromethyl-3-pyridinecarboxylic acid methyl ester, sodium salt (DPX-KE 459, flupyrsulfuron-methyl-sodium),
3-(4,6-Dimethoxypyrimidin-2-yl)-1-(3-N-methylsulfonyl-N-methyl-aminopyridin-2-yl)- sulfonylharnstoff oder dessen Salze (DE-A 40 00 503 und DE-A 40 30 577),3- (4,6-Dimethoxypyrimidin-2-yl) -1- (3-N-methylsulfonyl-N-methylaminopyridin-2-yl) sulfonylurea or its salts (DE-A 40 00 503 and DE-A 40 30 577),
1-(4,6-Dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)harnstoff1- (4,6-dimethoxypyrimidin-2-yl) -3- (3-trifluoromethyl-2-pyridylsulfonyl) urea
(Flazasulfuron), 1-(4,6-Dimethoxypyrimidin-2-yI)-3-[3-(2,2,2-trifluoroethoxy)-2- pyridylsulfonyl]harnstoff-Natriumsalz (TrifloxysuIfuron-natrium);(Flazasulfuron), 1- (4,6-Dimethoxypyrimidin-2-yI) -3- [3- (2,2,2-trifluoroethoxy) -2-pyridylsulfonyl] urea sodium salt (trifloxysulfuron sodium);
B6) Alkoxyphenoxysulfonylharnstoffe, z. B.B6) alkoxyphenoxysulfonylureas, e.g. B.
3-(4,6-Dimethoxypyrimidin-2-yl)-1 -(2-ethoxyphenoxy)-sulfonyIharnstoff oder dessen3- (4,6-Dimethoxypyrimidin-2-yl) -1 - (2-ethoxyphenoxy) sulfonylurea or its
Salze (Ethoxysulfuron);Salts (ethoxysulfuron);
B7) Imidazolylsulfonylharnstoffβ, z.B.B7) Imidazolylsulfonylurea β, e.g.
1-(4,6-Dimethoxypyrimidin-2-yl)-3-(2-ethylsuIfonylimidazo[1 ,2-a]pyridin-3- yl)sulfonylharstoff (MON 37500, Sulfosulfuron),1- (4,6-dimethoxypyrimidin-2-yl) -3- (2-ethylsulfonylimidazo [1, 2-a] pyridin-3-yl) sulfonyl urea (MON 37500, sulfosulfuron),
1-(2-Chloroimidazo[1 ,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2- yl)harnstoff (Imazosulfuron);1- (2-chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (imazosulfuron);
B8) Phenylaminosulfonylhamstoffe, z. B.B8) phenylaminosulfonylureas, e.g. B.
1-[2-(Cyclopropylcarbonyl)phenylaminosulfonyl]-3-(4,6-dimethoxypyrimidin-2- yl)hamstoff (Cyclosulfamuron);1- [2- (Cyclopropylcarbonyl) phenylaminosulfonyl] -3- (4,6-dimethoxypyrimidin-2-yl) urea (Cyclosulfamuron);
C) Chloracetanilide, z.B.C) chloroacetanilides, e.g.
Acetochlor, Alachlor, Butachlor, Dimethachlor, Dimethenamid, Metazachlor, Metolachlor, S-Metolachlor, Pethoxamid, Pretilachlor, Propachlor, Propisochlor und Thenylchlor;Acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, metazachlor, metolachlor, S-metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor and thenylchlor;
D) Thiocarbamate, z.B. S-Ethyl-N,N-dipropylthiocarbamat (EPTC), S-Ethyl-N,N-diisobutylthiocarbamat (Butylate),D) thiocarbamates, e.g. S-ethyl-N, N-dipropylthiocarbamate (EPTC), S-ethyl-N, N-diisobutylthiocarbamate (butylates),
Cycloate, Dimepiperate, Esprocarb, Molinate, Orbencarb, Pebulate, Prosulfocarb, Thiobencarb, Tiocarbazil und Tri-allate;Cycloate, Dimepiperate, Esprocarb, Molinate, Orbencarb, Pebulate, Prosulfocarb, Thiobencarb, Tiocarbazil and Tri-allate;
E) Cyclohexandionoxime, z.B.E) cyclohexanedione oximes, e.g.
Alloxydim, Butroxydim, Clethodim, Cloproxydim, Cycloxydim, Protoxydim, Sethoxydim, Tepraloxydim und Tralkoxydim; F) Imidazolinone, z.B.Alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, protoxydim, sethoxydim, tepraloxydim and tralkoxydim; F) Imidazolinones, e.g.
Imazamethabenz-methyl, Imazapic, Imazamox, Imazapyr, Imazaquin und Imazethapyr;Imazamethabenz-methyl, imazapic, imazamox, imazapyr, imazaquin and imazethapyr;
G) Triazolopyrimidinsulfonamid-Derivate, z.B.G) triazolopyrimidine sulfonamide derivatives, e.g.
Chloransulam-methyl, Diclosulam, Florasulam, Flumelsulam, Metosulam und Penoxulam;Chloransulam-methyl, diclosulam, florasulam, flumelsulam, metosulam and penoxulam;
H) Benzoylcyclohexandione, z.B.H) benzoylcyclohexanediones, e.g.
2-(2-Chlor-4-methylsulfonylbenzoyl)-cyclohexan-1 ,3-dion (SC-0051 , Sulcotrione),2- (2-chloro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione (SC-0051, Sulcotrione),
2-(2-Nitrobenzoyl)-4,4-dimethyI-cyclohexan-1 ,3-dion (EP-A 0 274 634),2- (2-nitrobenzoyl) -4,4-dimethyl-cyclohexane-1,3-dione (EP-A 0 274 634),
2-(2-Nitro-3-methylsulfonylbenzoyl)-4,4-dimethylcyclohexan-1 ,3-dion (WO2- (2-nitro-3-methylsulfonylbenzoyl) -4,4-dimethylcyclohexane-1,3-dione (WO
91/13548),91/13548)
2-[4-(Methylsulfonyl)-2-nitrobenzoyl]-1 ,3-cyclohexanedion (Mesotrione)2- [4- (methylsulfonyl) -2-nitrobenzoyl] -1, 3-cyclohexanedione (mesotrione)
I) Benzoylisoxazole, z. B.I) benzoylisoxazoles, e.g. B.
5-Cyclopropyl-[2-(methylsulfonyl)-4-(trifluoromethyI)benzoyl]-isoxazol (Isoxaflutole);5-cyclopropyl- [2- (methylsulfonyl) -4- (trifluoromethyl) benzoyl] isoxazole (isoxaflutole);
J) Benzoylpyrazole, z. B.J) Benzoylpyrazole, e.g. B.
2-[4-(2,4-Dichlor-m-toluoyl)-1 ,3-dimethylpyrazoI-5-yloxy]-4'-methylacetophenon2- [4- (2,4-dichloro-m-toluoyl) -1, 3-dimethylpyrazoI-5-yloxy] -4'-methylacetophenone
(Benzofenap),(Benzofenap),
4-(2,4-Dichlorbenzoyl)-1 ,3-dimethylpyrazol-5-yl toluene-4-sulfonate (Pyrazolynate),4- (2,4-dichlorobenzoyl) -1, 3-dimethylpyrazol-5-yl toluenes-4-sulfonate (pyrazolynate),
2-[4-(2,4-Dichlorbenzoyl)-1 ,3-dimethyIpyrazol-5-yloxy]acetophenone (Pyrazoxyfen);2- [4- (2,4-dichlorobenzoyl) -1, 3-dimethylIpyrazol-5-yloxy] acetophenone (pyrazoxyfen);
K) Sulfonylaminocarbonyltriazolinone, z. B.K) sulfonylaminocarbonyltriazolinones, e.g. B.
4,5-Dihydro-3-methoxy-4-methyl-5-oxo-Λ/-(2-trifluoromethoxyphenylsulfonyl)-1H- 1 ,2,4-triazole-1-carboxamide Natriumsalz (Flucarbazone-Natrium), 2-(4,5-Dihydro-4-methyl-5-oxo-3-propoxy-1 H-1 ,2,4-triazol-1 -yl)- carboxamidosulfonylbenzoesäure-methylester-NatriumsaΙz (Propoxycarbazone-Na);4,5-dihydro-3-methoxy-4-methyl-5-oxo-Λ / - (2-trifluoromethoxyphenylsulfonyl) -1H- 1, 2,4-triazole-1-carboxamide sodium salt (flucarbazone sodium), 2- ( 4,5-Dihydro-4-methyl-5-oxo-3-propoxy-1 H-1, 2,4-triazol-1-yl) - carboxamidosulfonylbenzoic acid methyl ester sodium salt (Propoxycarbazone-Na);
L) Triazolinone, z. B.L) triazolinones, e.g. B.
4-Amino-Λ/-fetτ-butyl-4,5-dihydro-3-isopropyl-5-oxo-1 ,2,4-1 H-triazole-1 -carboxamid (Amicarbazone),4-Amino-Λ / -fetτ-butyl-4,5-dihydro-3-isopropyl-5-oxo-1, 2,4-1 H-triazole-1-carboxamide (Amicarbazone)
2-(2,4-DichIor-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1 ,2,4-triazolo[4,3-a]pyridin- 3(2H)-one (Azafenidin),2- (2,4-dichloro-5-prop-2-ynyloxyphenyl) -5,6,7,8-tetrahydro-1, 2,4-triazolo [4,3-a] pyridin-3 (2H) -one (azafenidin),
(RS)-2-Chlor-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyI-5-oxo-1H-1 ,2,4- triazol-1-yl)-4-fluorophenyl]propionsäureethyIester (Carfentrazone-ethyl), 2,,4'-Dichlor-5,-(4-difluormethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1 ,2,4-triazol-1 -yi)- methanesulfonanilid (Sulfentrazone);(RS) -2-chloro-3- [2-chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1, 2,4-triazol-1-yl) -4-fluorophenyl] propionsäureethyIester (carfentrazone-ethyl), 2,, 4'-dichloro-5 - (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1, 2,4 -triazol-1-yi) - methanesulfonanilide (sulfentrazone);
M) Phosphinsäuren und Derivate, z. B.M) phosphinic acids and derivatives, e.g. B.
4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanin (Bilanafos), DL-Homoalanin-4-yl(methyl)phosphinsäure-ammoniumsalz (Glufosinate- ammonium);4- [hydroxy (methyl) phosphinoyl] -L-homoalanyl-L-alanyl-L-alanine (Bilanafos), DL-homoalanin-4-yl (methyl) phosphinic acid ammonium salt (glufosinate ammonium);
N) Glyzinderivate, z. B.N) glycine derivatives, e.g. B.
Λ/-(Phosphonomethyl)glyzin und dessen Salze (Glyphosate und Salze, z. B. dasΛ / - (phosphonomethyl) glycine and its salts (glyphosate and salts, e.g. the
Natriumsalz oder das Isopropylammoniumsalz),Sodium salt or the isopropylammonium salt),
Λ/-(Phosphonomethyl)glyzin-trimesiumsalz (Sulfosate);Λ / - (phosphonomethyl) glycine trimesium salt (sulfosate);
O) Pyrimidinyloxy-pyridincarbonsäure-Derivate bzw. Pyrimidinyloxybenzoesäure-Derivate, z.B.O) pyrimidinyloxy-pyridinecarboxylic acid derivatives or pyrimidinyloxybenzoic acid derivatives, e.g.
3-(4,6-Dimethoxypyrimidin-2-yl)-oxy-pyridin-2-carbonsäurebenzyl-ester (EP-A 0 249 707),3- (4,6-dimethoxypyrimidin-2-yl) -oxypyridine-2-carboxylic acid benzyl ester (EP-A 0 249 707),
3-(4,6-Dimethoxypyrimidin-2-yl)-oxy-pyridin-2-carbonsäuremethylester (EP-A 0 249 707),3- (4,6-dimethoxypyrimidin-2-yl) -oxypyridine-2-carboxylic acid methyl ester (EP-A 0 249 707),
2,6-Bis[(4,6-dimethoxypyrimidin-2-yl)-oxy]-benzoesäure-1-(ethoxycarbonyl-oxyethyl)- ester (EP-A 0472 113),2,6-bis [(4,6-dimethoxypyrimidin-2-yl) -oxy] -benzoic acid 1- (ethoxycarbonyl-oxyethyl) ester (EP-A 0472 113),
2,6-Bis[(4,6-dimethoxypyrimidin-2-yl)-oxy]-benzoesäure (Bispyribac-natrium), Pyribenzoxim, Pyriftalid, Pyriminobac-methyl und Pyrithiobac-natrium;2,6-bis [(4,6-dimethoxypyrimidin-2-yl) oxy] benzoic acid (bispyribac sodium), pyribenzoxime, pyriftalid, pyriminobac-methyl and pyrithiobac sodium;
P) S-(N-Aryl-N-alkyl-carbamoylmethyl)-dithiophosphonsäureester, wie S-[N-(4-P) S- (N-aryl-N-alkyl-carbamoylmethyl) dithiophosphonic acid esters, such as S- [N- (4-
Chlorphenyl)-N-isopropyl-carbamoylmethyl]-O,O-dimethyl-dithiophosphatChlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-dimethyl dithiophosphate
(Anilophos); Q) Triazinone, z. B.(Anilophos); Q) triazinones, e.g. B.
3-Cyclohexyl-6-dimethylamino-1 -methyl-1 ,3,5-triazine-2,4-(1 H,3H)-dion3-Cyclohexyl-6-dimethylamino-1-methyl-1, 3,5-triazine-2,4- (1H, 3H) -dione
(Hexazinone),(Hexazinone),
4-Amino-4,5-dihydro-3-methyl-6-phenyl-1 ,2,4-triazin-5-on (Metamitron),4-amino-4,5-dihydro-3-methyl-6-phenyl-1, 2,4-triazin-5-one (metamitron),
4-Amino-6-fe/f-butyl-4,5-dihydro-3-methylthio-1 ,2,4-triazin-5-on (Metribuzin);4-amino-6-fe / f-butyl-4,5-dihydro-3-methylthio-1, 2,4-triazin-5-one (metribuzin);
R) Pyridincarbonsäuren, z. B. Clopyralid, Fluroxypyr, Picloram und Triciopyr;R) pyridinecarboxylic acids, e.g. B. Clopyralid, Fluroxypyr, Picloram and Triciopyr;
S) Pyridine, z. B. Dithiopyr und Thiazopyr;S) pyridines, e.g. B. dithiopyr and thiazopyr;
T) Pyridincarboxamide, z. B. Diflufenican und Picolinafen;T) pyridinecarboxamides, e.g. B. Diflufenican and Picolinafen;
U) 1 ,3,5-Triazine, z. B.U) 1, 3,5-triazines, e.g. B.
Ametryn, Atrazine, Cyanazine, Dimethametrin, Prometon, Prometryn, Propazine,Ametryn, Atrazine, Cyanazine, Dimethametrin, Prometon, Prometryn, Propazine,
Simazine, Symetryn, Terbumeton, Terbuthylazine, Terbutryn und Trietazine;Simazine, Symetryn, Terbumeton, Terbuthylazine, Terbutryn and Trietazine;
V) Pflanzenwachstumsregulatoren, z. B. Forchlorfenuron und Thidiazuron.V) Plant growth regulators, e.g. B. Forchlorfenuron and thidiazuron.
Die Herbizide der Gruppen A bis V sind beispielsweise aus den oben jeweils genannten Schriften und aus "The Pesticide Manual", The British Crop Protection Council, 13th Edition, 2003, or the e-Pesticide Manual, Version 3.0, British Crop Protection Council 2003 bekannt.The herbicides of groups A to V are known, for example, from the publications mentioned above and from "The Pesticide Manual", The British Crop Protection Council, 13th Edition, 2003, or the e-Pesticide Manual, Version 3.0, British Crop Protection Council 2003 ,
Die Verbindungen der allgemeinen Formel (I) und deren Kombinationen mit einem oder mehreren der genannten Pestizide können in Abhängigkeit von den vorgegebenen chemisch-physikalischen und biologischen Parametern auf verschiedene Arten formuliert werden. Als Formulierungsarten sind beispielsweise geeignet:The compounds of the general formula (I) and their combinations with one or more of the pesticides mentioned can be formulated in various ways depending on the given chemical-physical and biological parameters. Examples of wording are: suitable:
Emulgierbare Konzentrate, die durch Auflösen der Wirkstoffe in einem organischen Lösungsmittel, z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höher siedenden Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt werden. Geeignete Emulgatoren sind beispielsweise alkylarylsulfonsaure Calcium-Salze, Fettsäurepolyglykolester, Alkyarylpolyglykolether, Fettalkoholpolyglykol-ether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester und Polyoxyethylensorbitanfettsäureester;Emulsifiable concentrates which are obtained by dissolving the active ingredients in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Suitable emulsifiers are, for example, alkylarylsulfonic acid calcium salts, fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene sorbitan fatty acid esters;
Stäubemittel, die durch Vermählen der Wirkstoffe mit fein-verteilten festen anorganischen oder organischen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, Diatomeenerde oder Mehlen erhalten werden. auf Wasser oder Öl basierende Suspensionskonzentrate, die beispielsweise durch Naßvermahlung mittels Perlmühlen hergestellt werden können; wasserlösliche Pulver; wasserlösliche Konzentrate;Dusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, diatomaceous earth or flours can be obtained. suspension concentrates based on water or oil, which can be prepared, for example, by wet grinding using bead mills; water soluble powder; water soluble concentrates;
Granulate, wie wasserlösliche Granulate, wasserdispergierbare Granulate sowie Granulate für die Streu- und Bodenapplikation;Granules, such as water-soluble granules, water-dispersible granules and granules for spreading and soil application;
Spritzpulver, die neben Wirkstoff noch Verdünnungs- oder Inertstoffe und Tenside enthalten;Wettable powders which, in addition to the active substance, also contain diluents or inert substances and surfactants;
Kapselsuspensionen und Mikrokapseln;Capsule suspensions and microcapsules;
Ultra-Low-Volume-Formulierungen.Ultra-low-volume formulations.
Die oben genannten Formulierungsarten sind dem Fachmann bekannt und werden beispielsweise beschrieben in: K. Martens, "Spray Drying Handbook", 3rd Ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y. 1973; Winnaker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Auflage 1986; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, N.Y. 1973, Seiten 8-57. Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; C. Marsden, "Solvents Guide", 2nd Ed., Interscience, N.Y. 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y.; Schönfeldt, "Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Auflage 1986.The above-mentioned types of formulation are known to the person skilled in the art and are described, for example, in: K. Martens, "Spray Drying Handbook", 3rd Ed., G. Goodwin Ltd., London. 1979; W. van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY 1973; Winnaker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, NY 1973, pp. 8-57. The necessary formulation aids such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; C. Marsden, Solvents Guide, 2nd Ed., Interscience, NY 1963; H. von Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, NY; Schönfeldt, "Interface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ; Winnacker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986.
Außer den vorstehend genannten Formulierungshilfsmitteln können die nutzpflanzenschützenden Mittel gegebenenfalls übliche Haft-, Netz-, Dispergier-, Penetrations-, Emulgier-, Konservierungs-, Frostschutz-, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer sowie den pH-Wert oder die Viskosität beeinflussende Mittel enthalten.In addition to the formulation auxiliaries mentioned above, the crop protection agents can optionally include customary adhesives, wetting agents, dispersants, penetrants, emulsifiers, preservatives, antifreeze agents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH or the like Contain viscosity-influencing agents.
Je nach Art der Formulierung enthalten die nutzpflanzenschützenden Mittel in der Regel 0,1 bis 99 Gew.-%, insbesondere 0,2 bis 95 Gew.-%, eines oder mehrerer Safener der allgemeinen Formel I oder eine Kombination von Safener und Pestizid. Weiterhin enthalten sie 1 bis 99,9, insbesondere 4 bis 99,5 Gew.-%, eines oder mehrerer fester oder flüssiger Zusatzstoffe und 0 bis 25, insbesondere 0,1 bis 25 Gew.-% eines Tensids. In emulgierbaren Konzentraten beträgt die Wirkstoffkonzentration, d.h. die Konzentration von Safener und/oder Pestizid, in der Regel 1 bis 90, insbesondere 5 bis 80 Gew.-%. Stäubemittel enthalten üblicherweise 1 bis 30, vorzugsweise 5 bis 20 Gew.-% Wirkstoff. In Spritzpulvern beträgt die Wirkstoffkonzentration in der Regel 10 bis 90 Gew.-%. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-% .Depending on the type of formulation, the crop protection agents generally contain 0.1 to 99% by weight, in particular 0.2 to 95% by weight, of one or more safeners of the general formula I or a combination of safener and pesticide. They also contain 1 to 99.9, in particular 4 to 99.5% by weight of one or more solid or liquid additives and 0 to 25, in particular 0.1 to 25% by weight of a surfactant. The active substance concentration in emulsifiable concentrates is the concentration of safener and / or pesticide, usually 1 to 90, in particular 5 to 80 wt .-%. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient. The active substance concentration in wettable powders is generally 10 to 90% by weight. The active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicherweise verdünnt, z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Granulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids u. a. variiert die erforderliche Aufwandmenge der Safener.For use, the formulations present in commercial 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. Dust-like preparations, granules and sprayable solutions are usually no longer diluted with other inert substances before use. The application rate of the safener varies with the external conditions, such as temperature, humidity, the type of herbicide used and others.
In den nachfolgenden Beispielen, die die Erfindung erläutern aber nicht limitieren, beziehen sich die Mengenangaben auf das Gewicht, wenn nicht Näheres definiert ist.In the following examples, which illustrate but do not limit the invention, the amounts given relate to the weight, unless otherwise specified.
A) Chemische BeispieleA) Chemical examples
Beispiel 1 : 3,4,5-Triacetoxy-benzoesäure-ethylesterExample 1: 3,4,5-Triacetoxy-benzoic acid ethyl ester
1.00 g (0.0047 Mol) Gallussäure-ethylester werden bei 0°C in 50 ml Dichlormethan vorgelegt, mit einer Spatelspitze Dimethylaminopyridin (DMAP) und anschließend mit 20 ml Acetanhydrid tropfenweise versetzt. Nach 18 Std. Rühren bei Raumtemperatur wird das Reaktionsgemisch im Vakuum eingengt, in Dichlormethan aufgenommen und anschließen mit Wasser und 5%iger Natriumbicarbonatlösung gewaschen. Nach dem Trocknen über Magnesiumsulfat und dem Einrotieren erhält man 1.43 g (90 % der Theorie) an dem gewünschten Produkt als Öl, das nach kurzer Zeit zu einer kristallinen Masse erstarrt. Smp. 76-78°C.1.00 g (0.0047 mol) of ethyl gallic acid are initially introduced into 50 ml of dichloromethane at 0 ° C., mixed with a spatula tip of dimethylaminopyridine (DMAP) and then dropwise with 20 ml of acetic anhydride. After stirring for 18 hours at room temperature, the reaction mixture is concentrated in vacuo, taken up in dichloromethane and then washed with water and 5% sodium bicarbonate solution. After drying over magnesium sulfate and spinning in, 1.43 g (90% of theory) of the desired product are obtained as an oil, which solidifies to a crystalline mass after a short time. Mp 76-78 ° C.
In der nachfolgenden Tabelle sind Beispiele für erfindungsgemäße Verbindungen (I) zusammengestellt: Examples of compounds (I) according to the invention are listed in the table below:
Tabelle 1 : Verbindungen der Formel (I)Table 1: Compounds of formula (I)
In der Tabelle 1 bedeutet:In Table 1 means:
Verb. Verbindung c = cyclo i = iso n = normal (geradkettig) s = sekundär t = tertiärVerb. Connection c = cyclo i = iso n = normal (straight-chain) s = secondary t = tertiary
Ac = AcetylAc = acetyl
Bu = n-Butyl n-Bu = n-ButylBu = n-butyl n-Bu = n-butyl
Et = EthylEt = ethyl
Me = Methyl n-Pr = n-Propyl i-Pr = Isopropyl c-Pr = Cyclopropyl i-Pen = Isopentyl B) Biologische BeispieleMe = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl i-Pen = isopentyl B) Biological examples
B1 ) Herbizid und Safener im Tankmix als Sprit∑applikationB1) Herbicide and safener in the tank mix as a fuel application
B1.1) Herbizid und Safener Vorauflaufanwendung im TankmischungsverfahrenB1.1) Herbicide and safener pre-emergence in the tank mix process
Samen verschiedener Kulturpflanzen und Unkrautarten wurden in runden Plastiklöpfen mit einem Durchmesser von 13 cm in einem sandigen Lehm Boden gesät und mit einer ca. 1 cm dicken Schicht sandigem Lehm bedeckt. Die Herbizide und die Safener in Form flüssiger (z.B. Emusionskonzentrate) oder trockener (z.B. wasserdispergierbare Pulver) Formulierungen, wurden auf die benötigten Konzentrationen mit deionisiertem Wasser verdünnt und mit einem Spritzschlitten unter Verwendung einer Wasseraufwandmenge von 300 Litern je Hektar auf die Bodenoberfläche appliziert. Im nachfolgend dargestellten Versuch wurden die Safener als 20 prozentige wasserdispergierbare Pulver, das Herbizid Isoxaflutole als wässriges Suspensionskonzentrat eingesetzt (siehe Tabelle 1.1.1). Die Töpfe wurden in einem Gewächshaus unter günstigen Wachstumsbedingungen aufgestellt. Eine optische Auswertung der herbiziden Wirkung wurde vier Wochen nach der Herbizidapplikation durchgeführt. Die Auswertung erfolgte auf einer prozentualen Basis im Vergleich zu unbehandelten Kontrollpflanzen (0% = keine erkennbare Wirkung im Vergleich zur unbehandelten Pflanze, 100% = behandelte Pflanze stirbt ab).Seeds of various crops and weeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam. The herbicides and the safeners in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were diluted to the required concentrations with deionized water and applied to the soil surface using a spray sled using a water application rate of 300 liters per hectare. In the experiment shown below, the safeners were used as 20 percent water-dispersible powders, the herbicide isoxaflutole as an aqueous suspension concentrate (see Table 1.1.1). The pots were placed in a greenhouse under favorable growing conditions. An optical evaluation of the herbicidal activity was carried out four weeks after the herbicide application. The evaluation was carried out on a percentage basis compared to untreated control plants (0% = no discernible effect compared to the untreated plant, 100% = treated plant dies).
Abkürzungen: Herbizid H1 = Isoxaflutole Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoβsäure (vgl Tab. 1) Verb. 1050 = 3,5-Dihydroxybenzoesäure (vgl. Tab. 1 ) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' SETVI Setaria viridis CHEAL Chenopodium album Abbreviations: Herbicide H1 = Isoxaflutole Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1) Verb. 1050 = 3,5-Dihydroxybenzoic acid (see Tab. 1) ZEAMA Zea mays (maize), variety ' Lorenzo 'SETVI Setaria viridis CHEAL Chenopodium album
B1.2) Nachauflaufanwendung von Herbizid und Safener im Tankmix-verfahrenB1.2) Post-emergence application of herbicide and safener in the tank mix process
Samen verschiedener Kulturpflanzen und Unkrautarten wurden in runden Plastiktöpfen mit einem Durchmesser von 13 cm in einem sandigen Lehmboden gesät und mit einer ca. 1 cm dicken Schicht sandigem Lehm bedeckt. Die Töpfe wurden in einem Gewächshaus unter günstigen Wachstumsbedingungen über eine Zeitdauer von ungefähr zwei bis drei Wochen aufgestellt, so dass die Pflanzen ein Wachstumsstadium von 2 bis 4 Blättern erreichten. Die Herbizide in Form flüssiger (z.B. Emusionskonzentrate) oder trockener (z.B. wasserdispergierbare Pulver) Formulierungen wurden mit einem Standardadditiv (auf Basis Rapsölmethylester) vermischt, auf die benötigten Konzentrationen mit deionisiertem Wasser verdünnt und mit einem Spritzschlitten unter Verwendung einer Wasseraufwandmenge von 300 Litern je Hektar auf die grünen Pflanzenteile und auf den unbedeckten Teil der Bodenoberfläche appliziert. Im nachfolgend dargestellten Versuch wurden die Safener und das Herbizid Foramsulfuron als jeweils 20 prozentige wasserdispergierbare Pulver verwendet (Ergebnisse siehe Tabelle 1.2.1).Seeds of various crops and weeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam. The pots were placed in a greenhouse under favorable growth conditions over a period of about two to three weeks so that the plants reached a growth stage of 2 to 4 leaves. The herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powder) formulations were mixed with a standard additive (based on rapeseed oil methyl ester), diluted to the required concentrations with deionized water and sprayed on using a water application rate of 300 liters per hectare the green parts of the plant and applied to the uncovered part of the soil surface. In the experiment shown below, the safeners and the herbicide foramsulfuron were each used as 20 percent water-dispersible powder (for results see Table 1.2.1).
Die Töpfe wurden in einem Gewächshaus unter günstigen Wachstumsbedingungen aufgestellt. Eine optische Auswertung der herbiziden Wirkung wurde vier Wochen nach der Herbizidapplikation durchgeführt. Die Auswerung erfolgte auf einer prozentualen Basis im Vergleich zu unbehandelten Kontrollpflanzen (0% = keine erkennbare Wirkung im Vergleich zur unbehandelten Pflanze, 100% = behandelte Pflanze stirbt ab).The pots were placed in a greenhouse under favorable growing conditions. An optical evaluation of the herbicidal activity was carried out four weeks after the herbicide application. The evaluation was carried out on a percentage basis compared to untreated control plants (0% = none recognizable effect compared to the untreated plant, 100% = treated plant dies).
Tabelle 1.2.1 : Nachauflaufanwendung: Herbizid und Safener im Tankmix- VerfahrenTable 1.2.1: Post-emergence application: herbicide and safener using the tank mix method
Abkürzungen: Herbizid H2 = Foramsulfuron Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoesäure (vgl Tab. 1) Verb. 1050 = 3,5-Dihydroxybenzoesäure (vgl. Tab. 1) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' SETVI Setaria viridis AMARE Amaranthus retroflexusAbbreviations: Herbicide H2 = Foramsulfuron Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1) Verb. 1050 = 3,5-Dihydroxybenzoic acid (see Tab. 1) ZEAMA Zea mays (maize), variety ' Lorenzo 'SETVI Setaria viridis AMARE Amaranthus retroflexus
B2) Safener als Saatgutbeizung gefolgt von HerbizidspritzapplikationB2) Safener as seed dressing followed by herbicide spray application
B2.1) SaatgutbehandlungB2.1) Seed treatment
Die Anzahl der Kulturpflanzensamen, die für jede Safeneraufwandmenge benötigt wird, wurde berechnet. Ausreichend Samen wurden in Glasflaschen mit Schraubverschluß eingewogen. Die Glasflaschen besaßen annähernd das doppelte Volumen der eingewogenen Samen. Die Safener wurden als 20 prozentige wasserdispergierbare Pulver formuliert. Diese Formulierungen wurden eingewogen, so dass die benötigten Aufwandmengen (g a.i./kg Saatgut) erzielt wurden. Die Proben wurden zu dem Saatgut in die Glasbehälter gegeben, anschließend wurde genügend Wasser zugegeben um eine geeignete Beizflüssigkeit zu bilden. Die Glasflaschen wurden verschlossen und dann in einen Überkopfschüttler gespannt (dieser drehte die Flaschen bei mittlerer Geschwindigkeit über eine Zeitdauer von bis zu einer Stunde), so dass die Saatkörner gleichmäßig mit der Beizflüssigkeit überzogen wurden. Die Flaschen wurden geöffnet und das Saatgut konnte in Vorauflauf- oder Nachauflaufversuchen, wie nachfolgend beschrieben, verwendet werden.The number of crop seeds required for each safener application rate was calculated. Sufficient seeds were weighed into screw-top glass bottles. The glass bottles had almost twice the volume of the weighed seeds. The safeners were formulated as 20 percent water dispersible powders. These formulations were weighed out so that the required application rates (g ai / kg seed) were achieved. The samples were added to the seeds in the glass containers, then enough water was added to form a suitable dressing liquid. The glass bottles were sealed and then placed in an overhead shaker (which rotated the bottles at medium speed for up to an hour) so that the seeds were evenly coated with the dressing liquid. The bottles were opened and the seed could be used in pre-emergence or post-emergence experiments as described below.
B2.2) Vorauflaufapplikation von Herbiziden nach Saatgutbeizung mit SafenerB2.2) Pre-emergence application of herbicides after seed dressing with safener
Die mit Safener behandelten Samen und unbehandelte Samen als Kontrollen wurden in runden Plastiktöpfen mit einem Durchmesser von 13 cm in einen sandigen Lehm Boden gesät und mit einer ca. 1 cm dicken Schicht sandigem Lehm bedeckt. Die Herbizide in Form flüssiger (z.B. Emusionskonzentrate) oder trockener (z.B. wasserdispergierbare Pulver) Formulierungen wurden auf die benötigten Konzentrationen mit deionisiertem Wasser verdünnt und mit einem Spritzschlitten unter Verwendung einer Wasseraufwandmenge von 300 Litern je Hektar auf die Bodenoberfläche appliziert. In den beiden nachfolgend dargestellten Versuchen (Ergebnisse siehe Tabellen 2.2.1 und 2.2.2) wurde das Herbizid Isoxaflutole als wässriges Suspensionskonzentrat eingesetzt.The seeds treated with safener and untreated seeds as controls were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam. The herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were diluted to the required concentrations with deionized water and applied to the soil surface using a spraying carriage using a water application rate of 300 liters per hectare. In the two experiments shown below (for results see Tables 2.2.1 and 2.2.2), the herbicide isoxaflutole was used as an aqueous suspension concentrate.
Die Töpfe wurden in einem Gewächshaus unter günstigen Wachstumsbedingungen aufgestellt. Eine optische Auswertung der herbiziden Wirkung wurde vier Wochen nach der Herbizidapplikation durchgeführt. Die Auswertung erfolgte auf einer prozentualen Basis im Vergleich zu unbehandelten Kontrollpflanzen (0% = keine erkennbare Wirkung im Vergleich zur unbehandelten Pflanze, 100% = behandelte Pflanze stirbt ab). Tabelle 2.2.1 : Herbizid im Vorauflauf nach Saatgutbehandlung mit SafenerThe pots were placed in a greenhouse under favorable growing conditions. An optical evaluation of the herbicidal activity was carried out four weeks after the herbicide application. The evaluation was carried out on a percentage basis compared to untreated control plants (0% = no discernible effect compared to the untreated plant, 100% = treated plant dies). Table 2.2.1: Pre-emergence herbicide after seed treatment with safener
Tabelle 2.2.2: Herbizid im Vorauflauf nach Saatgutbehandlung mit SafenerTable 2.2.2: Pre-emergence herbicide after seed treatment with safener
Abkürzungen in Tabellen 2.2.1 und 2.2.2:Abbreviations in tables 2.2.1 and 2.2.2:
Herbizid H1 = Isoxaflutole Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoesäure (vgl Tab. 1 ) Verb. 1050 = 3,5-Dihydroxybenzoesäure (vgl. Tab. 1 )Herbicide H1 = Isoxaflutole Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1) Verb. 1050 = 3,5-Dihydroxybenzoic acid (see Tab. 1)
ZEAMA Zea mays (Mais), Sorte 'Lorenzo' GLXMA Glycine max (Sojabohne), Sorte 'Lambert' B2.3) Nachauflaufapplikation von Herbiziden nach Saatgutbeizung mit SafenerZEAMA Zea mays (maize), variety 'Lorenzo' GLXMA Glycine max (soybean), variety 'Lambert' B2.3) Post-emergence application of herbicides after seed dressing with safener
Die mit Safener behandelten Samen und unbehandelte Samen wurden in runden Plastiktöpfen mit einem Durchmesser von 13 cm in einem sandigen Lehm Boden gesät und mit einer ca. 1 cm dicken Schicht sandigem Lehm bedeckt. Die Töpfe wurden in einem Gewächshaus unter günstigen Wachstumsbedingungen über eine Zeitdauer von ungefähr zwei bis drei Wochen aufgestellt, so dass die Pflanzen ein Wachstumsstadium von 2 bis 4 Blättern erreichten. Die Herbizide in Form flüssiger (z.B. Emusionskonzentrate) oder trockener (z.B. wasserdispergierbare Pulver) Formulierungen, wurden mit einem Standardadditiv (auf Basis Rapsölmethylester) vermischt, auf die benötigten Konzentrationen mit deionisiertem Wasser verdünnt und mit einem Spritzschlitten unter Verwendung einer Wasseraufwandmenge von 300 Litern je Hektar auf die grünen Pflanzenteile und auf den unbedeckten Teil der Bodenoberfläche appliziert. Im nachfolgend dargestellten Versuch wurde das Herbizid Foramsulfuron als 20 prozentiges wasserdispergierbares Pulver verwendet (Ergebnisse siehe Tabelle 2.3.1).The seeds treated with safener and untreated seeds were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam. The pots were placed in a greenhouse under favorable growth conditions over a period of about two to three weeks so that the plants reached a growth stage of 2 to 4 leaves. The herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powder) formulations were mixed with a standard additive (based on rapeseed oil methyl ester), diluted to the required concentrations with deionized water and with a spraying carriage using a water application rate of 300 liters per hectare applied to the green parts of the plant and to the uncovered part of the soil surface. In the experiment shown below, the herbicide foramsulfuron was used as a 20 percent water-dispersible powder (for results see Table 2.3.1).
Die Töpfe wurden in einem Gewächshaus unter günstigen Wachstumsbedingungen aufgestellt. Eine optische Auswertung der herbiziden Wirkung wurde vier Wochen nach der Herbizidapplikation durchgeführt. Die Auswertung erfolgte auf einer prozentualen Basis im Vergleich zu unbehandelten Kontrollpflanzen (0% = keine erkennbare Wirkung im Vergleich zur unbehandelten Pflanze, 100% = behandelte Pflanze stirbt ab). The pots were placed in a greenhouse under favorable growing conditions. An optical evaluation of the herbicidal activity was carried out four weeks after the herbicide application. The evaluation was carried out on a percentage basis compared to untreated control plants (0% = no discernible effect compared to the untreated plant, 100% = treated plant dies).
Tabelle 2.3.1 : Nachauflaufanwendung von Herbizid nach Saatgutbehandlung mit SafenerTable 2.3.1: Post-emergence application of herbicide after seed treatment with safener
Abkürzungen: Herbizid H2 = Foramsulfuron Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoesäure (vgl Tab. 1 ) Verb. 1050 = 3,5-Dihydroxybenzoesäure (vgl. Tab. 1) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' Abbreviations: Herbicide H2 = Foramsulfuron Verb. 1272 = 3,5-Dimethoxy-4-hydroxybenzoic acid (see Tab. 1) Verb. 1050 = 3,5-Dihydroxybenzoic acid (see Tab. 1) ZEAMA Zea mays (maize), variety ' Lorenzo '

Claims

Patentansprüche claims
1. Verwendung von Verbindungen der Formel (I) oder deren Salzen,1. Use of compounds of the formula (I) or their salts,
worin wherein
R1 Carboxy oder ein Derivat der Carboxylgruppe,R 1 carboxy or a derivative of the carboxyl group,
R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, SCN, CN oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oderR 2 and R 6 , each independently of one another, are hydrogen, halogen, SCN, CN or a hydrocarbon radical which is unsubstituted or substituted, R 3 (a) in the case n = 0 is a radical from the group consisting of hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or
(b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder(b) in the case of n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case of m = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or
(b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und(b) if m = 1, hydrogen or a radical of the formula A 2 , B 2 or C 2 and
Rb (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oderR b (a) in the case o = 0 is hydrogen or a radical of the formula A 3 or B 3 or
(b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, bedeutet, jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, einen Acylrest bedeutet und jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen heterocyclischen Rest, der unsubstituiert oder substituiert ist, bedeutet, Z, 11, Z", jeweils unabhängig voneinander, eine Gruppe der Formel O, S(O)x oder NR', wobei x = 0, 1 oder 2 ist und R' Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen Kohlenwasserstoffoxyrest, der unsubstituiert oder substituiert ist, oder Acyl oder Acyloxy bedeutet, m eiine ganze Zahl 0 oder 1 , n eiine ganze Zahl 0 oder 1 und(b) in the case o = 1, hydrogen or a radical of the formula A 3 , B 3 or C 3 , where each of the radicals A 1 , A 2 , A 3 , in each case independently of one another, is a hydrocarbon radical which is unsubstituted or substituted , each of the radicals B 1 , B 2 , B 3 , in each case independently of one another, is an acyl radical and each of the radicals C 1 , C 2 , C 3 , in each case independently of one another, is a heterocyclic radical which is unsubstituted or substituted, Z , 11, Z ", each independently of one another, a group of the formula O, S (O) x or NR ', where x = 0, 1 or 2 and R 'is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a hydrocarbonoxy radical which is unsubstituted or substituted or acyl or acyloxy, m is an integer 0 or 1, n is an integer Number 0 or 1 and
0 eiine ganze Zahl 0 oder 1 bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und B1, B2 beziehungsweise B3 ausgewählt ist, als Safener oder Resistenzinduktoren für Kultur- oder Nutzpflanzen.0 denotes an integer 0 or 1, the sum m + n + o giving an integer 1, 2 or 3 and, in the case of the alternatives (b) defined above, at least one of the radicals R 3 , R 4 and R 5 from radicals is selected from the group consisting of hydrogen and B 1 , B 2 or B 3 , as safeners or resistance inducers for crops or useful plants.
2. Verwendung nach Anspruch 1 , dadurch gekennzeichnet, dass R1 einen Rest der Formel2. Use according to claim 1, characterized in that R 1 is a radical of the formula
-CNCN
-C(=X)-Y-R oder-C (= X) -Y-R or
-C(=X)-Het, in welcher X einen divalenten Rest der Formel O, S oder NRa oder N-NRaRb bedeutet, wobei Ra und Rb wie unten definiert sind, Y eine Gruppe der Formel O, S, NRC oder NRc-NRdRe bedeutet, wobei-C (= X) -Het, in which X is a divalent radical of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, Y is a group of the formula O, S, NR C or NR c -NR d R e means, wherein
Rc, Rd und Re wie unten definiert sind, R Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen heterocyclischen Rest, der unsubstituiert oder substituiert ist, oder Acyl bedeutet, und Het einen aliphatischen N-Heterocyclus mit insgesamt 1 bis 4R c , R d and R e are as defined below, R is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclic radical which is unsubstituted or substituted or acyl, and Het is an aliphatic N-heterocycle with a total of 1 to 4
Heteroringatomen bedeutet, der mit einem N-Heteroringatom an dieHetero ring atoms means that with an N hetero ring atom to the
Gruppe C(=X) gebunden ist und der als Heteroringatome neben demGroup C (= X) is bound and the hetero ring atoms next to the
N-Atom in der yl-Position noch Heteroatome aus der Gruppe N, O undN atom in the yl position or heteroatoms from the group N, O and
S enthalten kann und der unsubstituiert oder substituiert ist, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und unabhängig vom Rest R wie für R definiert ist oder einen Rest der Formel -OR", wobei R* unabhängig von R wie für R definiert ist, bedeutet, bedeutet.S can contain and which is unsubstituted or substituted, wherein each of the radicals R a , R b , R c , R d and R e in the radicals X and Y are each independently of one another and independent of the radical R as defined for R or a radical of the formula -OR ", where R * is independent of R as defined for R means, means.
3. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass R1 einen Rest der Formel -C(=X)-Y-R oder -C(=X)-Het bedeutet, in welcher X einen divalenten Rest der Formel O, S oder NRa oder N-NRaRb, wobei3. Use according to claim 1 or 2, characterized in that R 1 is a radical of the formula -C (= X) -YR or -C (= X) -Het, in which X is a divalent radical of the formula O, S or NR a or N-NR a R b , where
Ra und Rb wie unten definiert sind, Y eine Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd undR a and R b are as defined below, Y is a group of formula O, S, NR C or NR c -NR d R e , where R c , R d and
Re wie unten definiert sind, R Wasserstoff, (d-C18)Alkyl, (C2-d8)Alkenyl, (C2-d8)Alkinyl.R e are as defined below, R is hydrogen, (dC 18 ) alkyl, (C 2 -d 8 ) alkenyl, (C 2 -d 8 ) alkynyl.
(C3-C9)Cycloalkyl, (C5-C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(CrC12)alkyl, Phenyl, Phenyl-(d-Cι2)alkyl, Heterocyclyl oder Heterocyclyl- (d-C12)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (d-C )Alkoxy, (C C )Haloalkoxy, (C2-C )Alkenyloxy, (C2-C )Haloalkenyloxy, (d~ C4)Alkylthio, (C C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (d- dJHaloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, Mono(d-C4)alkylamino, Di(Cι-C4)alkylamino, (d-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]-carbonyl, Di[(C-ι-C4)alkylamino]- carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder (CrC6)Alkanoyl, (d-C4)Haloalkanoyl, [(CrC )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl-(CrC4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (CrC4)Alkylsulfinyl, (d- C4)Alkylsulfonyl, (d-dJHaloalkylsulfinyl oder (Cι-C )Haloalkylsulfonyl, und inklusive Substituenten 1 bis 30 C-Atome, und(C 3 -C 9 ) cycloalkyl, (C 5 -C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (CrC 12 ) alkyl, phenyl, phenyl- (d-Cι 2 ) alkyl, heterocyclyl or heterocyclyl- ( dC 12 ) alkyl, each of the latter 10 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (dC) alkoxy, (CC) haloalkoxy, (C 2 -C) alkenyloxy , (C 2 -C) Haloalkenyloxy, (d ~ C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (d- dJHaloalkylsulfinyl, (Cι-C4) haloalkylsulfonyl, mono (dC 4 ) alkylamino , Di (-C-C 4 ) alkylamino, (dC 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [ (CrC 4 ) alkylamino] carbonyl, di [(C 1 -C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (C 1 -C 4 ) haloalkyl is substituted, or (CrC 6 ) Alkanoyl, (dC 4 ) haloalkanoyl, [(CrC) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (CrC 4 ) alkyl] -c arbonyl, [phenyl- (-C-C4) alkoxy] carbonyl, where each of the last 4 radicals in the phenyl ring is unsubstituted or substituted, aminocarbonyl, mono [(C 1 -C 4 ) alkylamino] carbonyl, di [(C 1 -C 4 ) alkylamino] carbonyl, (CrC 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (d-dJHaloalkylsulfinyl or (-C-C) haloalkylsulfonyl, and including substituents 1 to 30 carbon atoms, and
Het einen aliphatischen N-Heterocyclus mit insgesamt 1 bis 3Het an aliphatic N-heterocycle with a total of 1 to 3
Heteroringatomen und insgesamt 5 oder 6 Ringatomen, der mit einem N-Heteroringatom an die Gruppe C(=X) gebunden ist und der als Heteroringatome neben dem N-Atom in der yl-Position noch Heteroatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (d-C4)Alkyl, (d-C4)Alkoxy, (d- C4)Haloalkyl, (d-C )Haloalkoxy, (d-C4)Aikylthio und Oxo substituiert ist, bedeutet bzw. bedeuten, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und unabhängig vom Rest R wie für R definiert ist oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, bedeutet, und R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, SCN, CN, (d-Hetero ring atoms and a total of 5 or 6 ring atoms, which is bonded to the group C (= X) with an N hetero ring atom and which can also contain hetero atoms from the group N, O and S in addition to the N atom in the yl position as hetero ring atoms and the unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, amino, (dC 4) alkyl, (dC 4) alkoxy, (dC 4) haloalkyl, (dC) haloalkoxy, (dC 4) Aikylthio and oxo is substituted or mean, where each of the radicals R a , R b , R c , R d and R e in the radicals X and Y is each independently and independently of the radical R as defined for R or a radical of the formula -OR *, where R * is independent of R as defined for R, and R 2 and R 6 , each independently of one another, are hydrogen, halogen, SCN, CN, (d-
C4)Alkyl, (C2-C )Alkenyl, (C2-C4)Alkinyl oder (C3-C6)Cycloalkyl, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (d-C4)Alkoxy, (C1-C4)Haloalkoxy, (Cι-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C C4)Alkanoyl, (Cι-C )Haloalkanoyl, [(d-dJAlkoxyjcarbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(d-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-d)Alkyl und (Cι-C4)Haloalkyl substituiert ist, bedeuten und R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oder (b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder (b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und R5 (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oder (b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, Wasserstoff, (CrC-ιβ)Alkyl, (C2-C18)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl, (C5-C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(C Cι2)alkyl, Phenyl, Phenyl- (Cι-Cι2)alkyl, Heterocyclyl oder Heterocyclyl-(CrCι2)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C2- d)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (d- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)HaIoalkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C )Alkanoyl, (d-C4)Haloalkanoyl, [(Cι-C )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)aIkylamino]- carbonyl, Di[(CrC4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-d)Haloalkyl substituiert ist, bedeutet und wobei jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, (Cι-C6)Alkanoyl, (d-C4)Haloalkanoyl, [(CrC4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(d-C4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]- carbonyl, (d-C4)AIkyIsulfinyl( (CrC4)Alkylsulfonyl, (CrC4)Haloalkylsulfinyl oder (CrC4)HaIoalkylsulfonyl bedeutet und wobei jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen einen aliphatischen oder aromatischen Heterocyclus mit insgesamt 1 bis 3 Heteroringatomen aus der Gruppe N, O und S und insgesamt 5 oder 6 Ringatomen, und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (CrC4)Älkyl, (Cι-C4)Alkoxy, (d- C4)Haloalkyl, (Ci-dJHaloalkoxy, (Cι-C4)Alkylthio und Oxo substituiert ist, bedeutet und Z, Z\ Z", jeweils unabhängig voneinander, eine Gruppe der Formel O, S(O)x oder NR', wobei x = 0, 1 oder 2 ist und R' Wasserstoff, (CrC )Alkyl, (C2-C4)Alkenyl, (C2- C4)Alkinyl, (C3-C6)Cycloalkyl, (C C4)Alkoxy, (C2-C4)Alkenyloxy, (C2- C4)Alkinyloxy oder (C3-C6)Cycloalkyloxy, wobei jeder der letztgenannten 8 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (d-C4)Alkoxy. (d-C4)Haloalkoxy, (d-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d-C )Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (d- C )Haloalkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C )Alkanoyl, (CrC4)Haloalkanoyl, [(Cι-C )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (d-dJAlkyl und (Cι-d)Haloalkyl substituiert ist, oder (Cι-C6)Alkanoyl, (C C4)Haloalkanoyl, (d-CeJAlkanoyloxy, (Cι-C4)Haloalkanoyloxy, [(CrC4)Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, [(Cι-C4)Alkoxy]carbonyloxy, [(Cι-C4)Haloalkoxy]carbonyloxy, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C )alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Phenylcarbonyloxy, Phenoxycarbonyloxy, [Phenyl-(CrC4)alkyl]-carbonyloxy, oder [Phenyl- (Cι-C4)alkoxy]-carbonyloxy, wobei jeder der letztgenannten 8 Reste im Phenylring unsubstituiert oder substituiert ist, oder Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(d-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (d-C )Alkylsulfonyl, (C C4)Haloalkylsulfinyl oder (d- dJHaloalkylsulfonyl bedeutet, m eine ganze Zahl 0 oder 1 , n eine ganze Zahl 0 oder 1 und o eine ganze Zahl 0 oder 1 , bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und einem Rest der Formel B1, B2 bzw.C 4 ) alkyl, (C 2 -C) alkenyl, (C 2 -C 4 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy , Amino, cyano, nitro, thiocyanato, (dC 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, (Cι-C 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (CC 4 ) Haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (-C-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (CC 4 ) alkanoyl, (Cι-C) haloalkanoyl, [(d-dJalkoxyjcarbonyl, [( C 1 -C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(C 1 -C 4 ) alkylamino] carbonyl, di [(dC 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (Cι-d) alkyl and (Cι- C 4 ) is substituted haloalkyl, and R 3 (a) in the case n = 0 denotes a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or (b) in the case of n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case of m = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or (b) in the case m = 1 is hydrogen or a radical of the formula A 2 , B 2 or C 2 and R 5 (a) in the case o = 0 is hydrogen or a radical of the formula A 3 or B 3 or (b) in the case o = 1 is hydrogen or a radical of the formula A 3 , B 3 or C 3 , where each of the radicals A 1 , A 2 , A 3 , in each case independently of one another, is hydrogen, (CrC-ιβ) alkyl, (C 2 -C 18 ) alkenyl, (C 2 -C 18 ) alkynyl, (C 3 -C 9 ) cycloalkyl, (C 5 -C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (C Cι 2 ) alkyl, phenyl, phenyl- (Cι-Cι 2 ) alkyl, heterocyclyl or heterocyclyl- (CrCι 2 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, Thiocyanato, (-C-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 - d) alkenyloxy, (C 2 -C 4 ) haloalkenylo xy, (dC 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι- C 4 ) alkylamino, (-C-C) alkanoyl, (dC 4 ) haloalkanoyl, [(Cι-C) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) akylamino ] - carbonyl, di [(CrC 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (Cι-d) haloalkyl is substituted, and each of the radicals B 1 , B 2 , B 3 , in each case independently of one another, (C 1 -C 6 ) alkanoyl, (dC 4 ) haloalkanoyl, [(CrC 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι- C 4 ) alkyl] -carbonyl, [phenyl- (-C-C 4 ) alkoxy] -carbonyl, each of the latter 4 radicals in the phenyl ring being unsubstituted or substituted, aminocarbonyl, mono [(dC 4 ) alkylamino] carbonyl, di [ (-C-C 4 ) alkylamino] - carbonyl, (dC 4 ) alkylisulfinyl ( (CrC 4 ) alkylsulfonyl, (CrC 4 ) haloalkylsulfinyl or (CrC 4 ) HaI means oalkylsulfonyl and where each of the radicals C 1 , C 2 , C 3 , in each case independently of one another, means an aliphatic or aromatic heterocycle with a total of 1 to 3 hetero ring atoms from the group N, O and S and a total of 5 or 6 ring atoms, and which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (CrC 4 ) alkyl, (-C-C 4 ) alkoxy, (d-C 4 ) haloalkyl, (Ci-dJHaloalkoxy, (-C-C 4 ) alkylthio and oxo is substituted, means and Z, Z \ Z ", in each case independently of one another, a group of the formula O, S (O) x or NR ', where x = 0, 1 or 2 and R' is hydrogen, (CrC) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (CC 4 ) alkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 - C 4 ) alkynyloxy or (C 3 -C 6 ) cycloalkyloxy, each of the latter 8 residues being unsubstituted or by one or more radicals from the group consisting of halogen, hydroxy, amino, cyano, nitro, thiocyanato, (dC 4 ) alkoxy. (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC) alkylsulfonyl, (Cι- C 4 ) haloalkylsulfinyl, (d- C) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (Cι-C) alkanoyl, (CrC 4 ) haloalkanoyl, [(Cι-C) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [( Cι-C 4 ) alkylamino] - carbonyl, di [(Cι-C 4 ) alkylamino] -carbonyl and in the case of cyclic radicals also (d-dJAlkyl and (Cι-d) haloalkyl is substituted, or (Cι-C 6 ) alkanoyl , (CC 4 ) haloalkanoyl, (d-CeJalkanoyloxy, (Cι-C 4 ) haloalkanoyloxy, [(CrC 4 ) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, [(Cι-C 4 ) alkoxy] carbonyloxy, [ (Cι-C 4 ) haloalkoxy] carbonyloxy, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C) alkyl] -carbonyl, [phenyl- (CrC 4 ) alkoxy] -carbonyl, phenylcarbonyloxy, phenoxycarbonyloxy, [phenyl- (CrC 4 ) alkyl] -carbonyloxy, or [phenyl- (-C-C 4 ) alkoxy] -carbonyloxy, where each of the latter 8 radicals in the phenyl ring is unsubstituted or substituted, or aminocarbonyl, mono [(-C-C 4 ) alkylamino] -carbonyl, Di [(dC 4 ) alkylamino] carbonyl, (d- C 4 ) alkylsulfinyl, (dC) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl, or (d- d JHaloalkylsulfonyl, m is an integer 0 or 1, n is an integer 0 or 1 and o is an integer 0 or 1, where the sum m + n + o is an integer 1, 2 or 3 and, in the case of the alternatives (b) defined above, at least one of the radicals R. 3 , R 4 and R 5 from radicals from the group consisting of hydrogen and a radical of the formula B 1 , B 2 or
B3 ausgewählt ist.B 3 is selected.
4. Verwendung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass4. Use according to one of claims 1 to 3, characterized in that
R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oder (b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder (b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und R5 (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oder (b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, Wasserstoff, (d-C^Alkyl, (C2-C12)Alkenyl, (C2-C12)Alkinyl, (C3-C6)Cycloalkyl, (C5-C6)Cycloalkenyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, Phenyl, Phenyl- (Cι-C )alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (d- C4)Alkoxy, (d-C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2- C4)Haloalkenyloxy, (Cι-C4)Alkylthio, (C C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (Cι-C )Haloalkylsulfonyl, Mono(Cι-C )alkylamino, Di(Cι-C4)aIkylamino, (d-C )Alkanoyl, (CrC4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(d-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(d-C )alkylamino]-carbonyl und im Falle cyclischer Reste auch (CrC )Alkyl und (d-C4)Haloalkyl substituiert ist, bedeutet und wobei jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, (CrC4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, (d- C )Alkylsulfinyl, (Cι-C )Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (d- C )Haloalkylsulfonyl bedeutet und wobei jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen aliphatischen oder aromatischen Heterocyclus mit insgesamt 1 bis 3 Heteroringatomen aus der Gruppe N, O und S und insgesamt 5 oder 6 Ringatomen, und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d-C )Alkyl, (C C4)Alkoxy, (C C4)Haloalkyl, (d- C )HaIoalkoxy, (C1-C4)Alkylthio und Oxo substituiert ist, bedeutet, undR 3 (a) in the case of n = 0, a radical from the group consisting of hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or (b) in the case of n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case of m = 0, a radical from the group consisting of hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or (b) in the case of m = 1, hydrogen or one A radical of the formula A 2 , B 2 or C 2 and R 5 (a) in the case o = 0 is hydrogen or a radical of the formula A 3 or B 3 or (b) in the case o = 1 is hydrogen or a radical of the formula A 3 , B 3 or C 3 , each of the radicals A 1 , A 2 , A 3 , each independently of one another, hydrogen, (dC ^ alkyl, (C 2 -C 12 ) alkenyl, (C 2 -C 12 ) alkynyl, ( C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl, phenyl, phenyl- (Cι-C) alkyl, heterocyclyl or heterocyclyl- (-C-C 4 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the group halogen, hydroxy, A mino, (d- C 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 - C 4 ) haloalkenyloxy, (Cι-C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (Cι-C) haloalkylsulfonyl, mono (Cι-C) alkylamino, di (Cι-C 4 ) aIkylamino, (dC) alkanoyl, (CrC 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(dC 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] - carbonyl, di [(dC) alkylamino] carbonyl and in the case of cyclic radicals also (CrC) alkyl and (dC 4 ) haloalkyl is substituted, and each of the radicals B 1 , B 2 , B 3 , in each case independently of one another, ( CrC 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(-C-C 4 ) alkoxy] carbonyl, (d- C) alkylsulfinyl, (Cι-C) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (d- C) haloalkylsulfonyl and where each of the radicals C 1 , C 2 , C 3 , each independently of one another, is an aliphatic or aromatic heterocycle having a total of 1 to 3 hetero ring atoms from the group N, O and S and a total of 5 or 6 ring atoms, and which is unsubstituted or by one or more radicals from the group halogen, (dC) alkyl, (CC 4 ) alkoxy, (CC 4 ) haloalkyl, (d-C) haloalkoxy, (C 1 -C 4 ) alkylthio and oxo is substituted, and
Z, Z', Z", jeweils unabhängig voneinander, eine Gruppe der Formel O, S, SO, SO2 oder NR', in dem R' Wasserstoff, (Cι-C4)Alkyl, (C3-C6)Cycloalkyl oder (d-C4)Alkoxy. wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio und im Falle cyclischer Reste auch (d-C )Alkyl und (d-C4)Haloalkyl substituiert ist, oder (d-C6)Alkanoyl, (d-C4)Haloalkanoyl, (d-C6)Alkanoyloxy, (d-dJHaloalkanoyloxy, [(d-dJAlkoxyjcarbonyl, Phenylcarbonyl, [Phenyl- (C1-C4)alkyl]-carbonyl oder [Phenyl-(CrC4)alkoxy]-carbonyl, wobei jeder der letztgenannten 3 Reste im Phenylring unsubstituiert oder substituiert ist, oder (d-dJAlkylsulfinyl oder (Cι-C4)Alkylsulfonyl bedeutet, und m eine ganze Zahl 0 oder 1 , n eine ganze Zahl 0 oder 1 und o eine ganze Zahl 0 oder 1 , bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und einem Rest der Formel B1, B2 bzw. B3 ausgewählt ist.Z, Z ', Z ", in each case independently of one another, a group of the formula O, S, SO, SO 2 or NR', in which R 'is hydrogen, (-CC 4 ) alkyl, (C 3 -C 6 ) cycloalkyl or (dC 4 ) alkoxy, where each of the latter 3 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio and in the case of cyclic residues also (dC) alkyl and (dC 4 ) haloalkyl is substituted, or (dC 6 ) alkanoyl, (dC 4 ) haloalkanoyl, (dC 6 ) alkanoyloxy, (d-dJHaloalkanoyloxy, [(d-dJalkoxyjcarbonyl, phenylcarbonyl, [phenyl- (C 1 -C 4 ) alkyl] -carbonyl or [phenyl- (CrC 4 ) alkoxy] -carbonyl, where each of the last 3 radicals in the phenyl ring is unsubstituted or substituted, or (d-dJ-alkylsulfinyl or (-C-C 4 ) alkylsulfonyl), and m is an integer 0 or 1, n is an integer 0 or 1 and o is an integer 0 or 1, the sum m + n + o being an integer 1, 2 or 3 and in the case of those defined above Alternatives (b) at least one of the radicals R 3 , R 4 and R 5 from radicals from the group consisting of hydrogen and a radical of the formula B 1 , B 2 or B 3 is selected.
5. Verwendung nach einem der Ansprüche 2 bis 4, dadurch gekennzeichnet,5. Use according to one of claims 2 to 4, characterized in
R1 einen Rest der FormelR 1 is a radical of the formula
-CO-OR-CO-OR
-C(=NRa)-OR oder-C (= NR a ) -OR or
-CO-NRcR bedeutet, wobei jeder der Reste R, Ra, Rb und Rc die definierte Bedeutung hat.-CO-NR c R means, where each of the radicals R, R a , R b and R c has the defined meaning.
6. Verwendung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass die Verbindungen der Formel (I) als Safener gegen phytotoxische Wirkungen von Agrochemikalien an diesen Pflanzen eingesetzt werden.6. Use according to one of claims 1 to 5, characterized in that the compounds of formula (I) are used as safeners against phytotoxic effects of agrochemicals on these plants.
7. Verwendung nach Anspruch 6, dadurch gekennzeichnet, dass die Verbindungen der Formel (I) als Safener gegen phytotoxische Wirkungen von Pestiziden aus der Gruppe der Herbizide, Insektizide, Akarizide, Nematizide und Fungizide eingesetzt werden.7. Use according to claim 6, characterized in that the compounds of formula (I) are used as safeners against phytotoxic effects of pesticides from the group of herbicides, insecticides, acaricides, nematicides and fungicides.
8. Verwendung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass die Verbindungen der Formel (I) zum Schutz der Pflanzen gegen schädliche Umweltfaktoren eingesetzt werden.8. Use according to one of claims 1 to 5, characterized in that the compounds of formula (I) are used to protect the plants against harmful environmental factors.
9. Verwendung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass die Verbindungen der Formel (I) als Resistenzinduktor in den Pflanzen gegen Infektion durch Krankheitserreger eingesetzt werden.9. Use according to one of claims 1 to 5, characterized in that the compounds of formula (I) are used as a resistance inducer in the plants against infection by pathogens.
10. Verfahren zum Schützen von Nutz- oder Kulturpflanzen vor phytotoxischen Nebenwirkungen von Agrochemikalien, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der Formel (I), wie sie nach einem der Ansprüche 1 bis 6 definiert sind, vor, nach oder gleichzeitig mit dem oder den Agrochemikalien auf die Pflanzen, Pflanzenteile, Pflanzensamen oder das Saatgut appliziert.10. A method for protecting useful or crop plants against phytotoxic side effects of agrochemicals, characterized in that an effective amount of one or more compounds of the formula (I), as defined according to one of claims 1 to 6, before, after or simultaneously with the agrochemical (s) on the plants, parts of plants, plant seeds or that Seed applied.
11. Verfahren nach Anspruch 10, dadurch gekennzeichnet, dass die Applikation im Nachauflaufverfahren erfolgt.11. The method according to claim 10, characterized in that the application takes place in the post-emergence process.
12. Verfahren nach Anspruch 10, dadurch gekennzeichnet, dass die Applikation durch Behandlung der Pflanzensamen oder des Saatguts erfolgt.12. The method according to claim 10, characterized in that the application is carried out by treating the plant seeds or the seeds.
13. Verfahren nach Anspruch 10, dadurch gekennzeichnet, dass die Applikation im Vorauflaufverfahren erfolgt.13. The method according to claim 10, characterized in that the application takes place in the pre-emergence process.
14. Verbindungen der Formel (I) oder deren Salze,14. Compounds of the formula (I) or their salts,
worin wherein
R1 einen Rest der FormelR 1 is a radical of the formula
-CO-OR oder-CO-OR or
-C(=NRa)-OR oder-C (= NR a ) -OR or
-CO-NRcR, R Wasserstoff, (Cι-Cι8)Alkyl. (C2-C18)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl,-CO-NR c R, R hydrogen, (-CC 8 ) alkyl. (C 2 -C 18 ) alkenyl, (C 2 -C 18 ) alkynyl, (C 3 -C 9 ) cycloalkyl,
(C5-C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(C1-Cι2)alkyl, Phenyl, Phenyl-(C 5 -C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (C 1 -Cι 2 ) alkyl, phenyl, phenyl-
(Cι-Ci2)alkyl, Heterocyclyl oder Heterocyclyl-(CrCi2)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (Cι-C4)Alkoxy, (Cr C )Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C )Haloalkenyloxy, (d- C4)Alkylthio, (C C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d- C4)Haloalkylsulfinyl, (C C4)Haloalkylsulfonyl, Mono(Cι-C )alkylamino, Di(Cι-C )alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]- carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder (Cι-C6)Alkanoyl, (CrC )Haloalkanoyl, [(d-C4)AlkoxyJcarbonyl. [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (CrC )alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(d-C4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]- carbonyl, (Cι-C4)Alkylsulfinyl, (CrC4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl oder (CrC4)Haloalkylsulfonyl, Het einen aliphatischen N-Heterocyclus mit insgesamt 1 bis 3 Heteroringatomen und insgesamt 5 oder 6 Ringatomen, der mit einem N-Heteroringatom an die Gruppe C(=X) gebunden ist und der als Heteroringatome neben dem N-Atom in der yl-Position noch Heteroatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (Cι-C4)Alkyl, (d-C4)Alkoxy, (Cr C4)Haloalkyl, (d-C4)Haloalkoxy, (Cι-C4)Alkylthio und Oxo substituiert ist, wobei jeder der Reste Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und unabhängig vom Rest R wie für R definiert ist oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, R2 und R6, jeweils unabhängig voneinander, Wasserstoff, Halogen, SCN, CN, (d- C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl oder (C3-C6)Cycloalkyl, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (C1-C4)Alkoxy, (Cι-C )Haloalkoxy, (Cι-C4)Alkylthio, (Cι-C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (d- C )Haloalkylsulfonyl, Mono(d-C4)alkylamino, Di(d-C4)alkylamino, (Cι-C4)Alkanoyl, (C-ι-C4)Haloalkanoyl, [(CrC )Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, R3 (a) im Fall n = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A1 oder B1 oder (b) im Fall n = 1 Wasserstoff oder einen Rest der Formel A1, B1 oder C1 und R4 (a) im Fall m = 0 einen Rest aus der Gruppe Wasserstoff, Halogen, SCN und CN oder einen Rest der Formel A2 oder B2 oder (b) im Fall m = 1 Wasserstoff oder einen Rest der Formel A2, B2 oder C2 und R5 (a) im Fall o = 0 Wasserstoff oder einen Rest der Formel A3 oder B3 oder (b) im Fall o = 1 Wasserstoff oder einen Rest der Formel A3, B3 oder C3, wobei jeder der Reste A1, A2, A3, jeweils unabhängig voneinander, Wasserstoff, (Cι-C18)Alkyl, (C2-C18)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl, (C5-C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(d-C12)alkyl, Phenyl, Phenyl- (Cι-Ci2)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-Ci2)alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (Cι-d)Alkoxy, (Cι-C4)Haloalkoxy, (C2- C )Alkenyloxy, (C2-C4)Haloalkenyloxy, (Cι-C4)Alkylthio, (C C4)Alkylsulfinyl, (d-dJAlkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (C C4)Alkanoyl, (d-C4)Haloalkanoyl. [(d-C4)Alkoxy]carbonyl, [(d-dJHaloalkoxyjcarbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, bedeutet und inklusive Substituenten 1 bis 30 C-Atome, vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 16 C-atome aufweist, wobei jeder der Reste B1, B2, B3, jeweils unabhängig voneinander, (Cι-C6)Alkanoyl, (C C4)Haloalkanoyl, [(C C )Alkoxy]carbonyl, [(CrC )Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(d-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(CrC )alkylamino]- carbonyl, (d-C4)AlkylsuIfinyl, (Cι-C4)Alkylsulfonyl, (Cι-C )Haloalkylsulfinyl oder (Cι-C4)HaloalkylsuIfonyl bedeutet, wobei jeder der Reste C1, C2, C3, jeweils unabhängig voneinander, einen einen aliphatischen oder aromatischen Heterocyclus mit insgesamt 1 bis 3 Heteroringatomen aus der Gruppe N, O und S und insgesamt 5 oder 6 Ringatomen, und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, (d-C4)Alkyl, (CrC4)Alkoxy, (d- C4)Haloalkyl, (d-C4)Haloalkoxy, (d-C4)Alkylthio und Oxo substituiert ist, bedeutet, ", jeweils unabhängig voneinander, eine Gruppe der Formel O, S(O)x oder NR', wobei x = 0, 1 oder 2 ist und R' Wasserstoff, (C1-C4)Alkyl, (C2-C4)Alkenyl, (C2- C4)Alkinyl, (C3-C6)Cycloalkyl, (C C4)Alkoxy, (C2-C4)Alkenyloxy, (C2- C4)Alkinyloxy oder (C3-C6)Cycloalkyloxy, wobei jeder der letztgenannten 8 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (C1-C4)Alkylthio, (C C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C )Haloalkylsulfinyl, (C C4)Haloalkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C )alkylamino, (Cι-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(CrC )Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-d)Alkyl und (d-C4)Haloalkyl substituiert ist, oder (d-C6)Alkanoyl, (CrC4)Haloalkanoyl, (d-C6)Alkanoyloxy, (CrC4)Haloalkanoyloxy, [(CrC4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, [(Cι-C4)Alkoxy]carbonyloxy, [(Cι-C4)Haloalkoxy]carbonyloxy, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Phenylcarbonyloxy, Phenoxycarbonyloxy, [Phenyl-(Cι-C4)alkyl]-carbonyloxy, oder [Phenyl- (Cι-C4)alkoxy]-carbonyloxy, wobei jeder der letztgenannten 8 Reste im Phenylring unsubstituiert oder substituiert ist, oder Aminocarbonyl, Mono[(CrC4)alkylamino]-carbonyl, Di[(d-C4)aIkylamino]-carbonyl, (Ci- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (Cι-C )Haloalkylsulfinyl oder (Ci- C )Haloalkylsulfonyl bedeutet, m eiine ganze Zahl 0 oder 1 , n eiine ganze Zahl 0 oder 1 und(-C-Ci 2 ) alkyl, heterocyclyl or heterocyclyl- (CrCi 2 ) alkyl, where each of the last 10 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (Cι-C 4 ) alkoxy, (Cr C) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C) haloalkenyloxy, (d- C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (d- C 4 ) haloalkylsulfinyl, (CC 4 ) haloalkylsulfonyl, mono (-C-C) alkylamino, di (Cι-C) alkylamino, (Cι-C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] - carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, or (-C-C 6 ) alkanoyl, (CrC) haloalkanoyl, [(dC 4 ) alkoxyJcarbonyl. [(-C-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (CrC) alkyl] -carbonyl, [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, each of the latter 4 residues in the phenyl ring being unsubstituted or is substituted, aminocarbonyl, mono [(dC 4 ) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl, (Cι-C 4 ) alkylsulfinyl, (CrC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl or ( CrC 4 ) Haloalkylsulfonyl, Het an aliphatic N-heterocycle with a total of 1 to 3 hetero ring atoms and a total of 5 or 6 ring atoms, which is bonded to the group C (= X) with an N-hetero ring atom and which as a hetero ring atom next to the N atom in the yl position can also contain heteroatoms from the group N, O and S and which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (C 1 -C 4 ) alkyl, (dC 4 ) alkoxy, (Cr C 4 ) haloalkyl, (dC 4 ) haloalkoxy, (-C-C 4 ) alkylthio and oxo is substituted, each of the radicals R a , R b , R c , R d and R e in the radicals X and Y is each independently of one another and independent of the radical R as defined for R or a radical of the formula -OR *, where R * is independent of R as defined for R, R 2 and R 6 , each independently of one another, hydrogen, halogen, SCN , CN, (d-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl or (C 3 -C 6 ) cycloalkyl, each of the latter 4 radicals being unsubstituted or by one or more Residues from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (Cι-C) haloalkoxy, (Cι-C 4 ) alkylthio, (Cι-C 4 ) alkylsulfinyl, (Cι -C 4 ) alkylsulfonyl, (-C-C 4 ) haloalkylsulfinyl, (d- C) haloalkylsulfonyl, mono (dC 4 ) alkylamino, di (dC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (C-ι-C 4 ) Haloalkanoyl, [(CrC) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] - carbonyl, di [(C 1 -C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (C 1 -C 4 ) haloalkyl is substituted, R 3 (a) in the case n = 0 is a radical from the Group hydrogen, halogen, SCN and CN or a radical of the formula A 1 or B 1 or (b) in the case n = 1 hydrogen or a radical of the formula A 1 , B 1 or C 1 and R 4 (a) in the case m = 0 a radical from the group hydrogen, halogen, SCN and CN or a radical of the formula A 2 or B 2 or (b) in the case m = 1 hydrogen or a radical of the formula A 2 , B 2 or C 2 and R 5 (a) in the case o = 0 hydrogen or a radical of the formula A 3 or B 3 or (b) in the case o = 1 hydrogen or a radical of the formula A 3 , B 3 or C 3 , where each of the radicals A 1 , A 2 , A 3 , each independently of one another, hydrogen, (C 1 -C 18 ) alkyl, (C 2 -C 18 ) alkenyl, (C 2 -C 18 ) alkynyl, (C 3 -C 9 ) cycloalkyl, (C 5 -C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (dC 12 ) alkyl, phenyl, phenyl- (-C-Ci 2 ) alkyl, heterocyclyl or heterocyclyl- ( Cι-Ci 2 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (Cι-d) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 - C) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (Cι-C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (d-dJalkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, Mono (CrC 4 ) alkylamino, di (-C 4 ) alkylamino, (CC 4 ) alkanoyl, (dC 4 ) haloalkanoyl. [(dC 4 ) alkoxy] carbonyl, [(d-dJHaloalkoxyjcarbonyl, aminocarbonyl, mono [(-C-C 4 ) alkylamino] - carbonyl, di [(Cι-C 4 ) alkylamino] -carbonyl and in the case of cyclic radicals also (Cι -C 4 ) alkyl and (-C-C 4 ) haloalkyl is substituted, and includes substituents 1 to 30 C atoms, preferably 1 to 20 C atoms, in particular 1 to 16 C atoms, each of the radicals B 1 , B 2 , B 3 , each independently, (-C-C 6 ) alkanoyl, (CC 4 ) haloalkanoyl, [(CC) alkoxy] carbonyl, [(CrC) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι -C 4 ) alkyl] carbonyl, [phenyl- (dC 4 ) alkoxy] carbonyl, each of which the last 4 radicals in the phenyl ring is unsubstituted or substituted, aminocarbonyl, mono [(C 1 -C 4 ) alkylamino] carbonyl, di [(CrC) alkylamino] carbonyl, (dC 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, ( Cι-C) Haloalkylsulfinyl or (-Cι-C 4 ) HaloalkylsuIfonyl means, each of the radicals C 1 , C 2 , C 3 , each independently of the other, an aliphatic or aromatic heterocycle with a total of 1 to 3 hetero ring atoms from the group N, O and S and a total of 5 or 6 ring atoms, and which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (dC 4 ) alkyl, (CrC 4 ) alkoxy, (d- C 4 ) haloalkyl, (dC 4 ) Haloalkoxy, (dC 4 ) alkylthio and oxo is substituted, means ", in each case independently of one another, a group of the formula O, S (O) x or NR ', where x = 0, 1 or 2 and R' is hydrogen, (C 1 -C 4) alkyl, (C 2 -C 4) alkenyl, (C 2 - C 4) alkynyl, (C 3 -C 6) cycloalkyl, (CC 4) alkoxy, (C 2 -C 4) alkenyloxy , (C 2 - C 4 ) alkynyloxy or ( C 3 -C 6 ) cycloalkyloxy, where each of the latter 8 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC) haloalkylsulfinyl, (CC 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι-C) alkylamino, (Cι-C 4 ) Alkanoyl, (dC 4 ) haloalkanoyl, [(CrC) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] - carbonyl, di [(Cι-C 4 ) alkylamino] - carbonyl and in the case of cyclic radicals also (-CC) alkyl and (dC 4 ) haloalkyl is substituted, or (dC 6 ) alkanoyl, (CrC 4 ) haloalkanoyl, (dC 6 ) alkanoyloxy, (CrC 4 ) haloalkanoyloxy, [(CrC 4 ) alkoxy] carbonyl, [(-C-C 4 ) haloalkoxy] carbonyl, [(Cι-C 4 ) alkoxy] carbonyloxy, [(Cι-C 4 ) haloalkoxy] carbonyloxy, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) alkyl] carbonyl, [phenyl- (CrC 4 ) alkoxy] carbonyl, phenylcarbonyloxy, phenoxycarbonyloxy, [Phenyl- (-C 4 ) alkyl] carbonyloxy, or [Phenyl- (-C 4 ) alkoxy] carbonyloxy, each of the latter 8 residues in Phenyl ring is unsubstituted or substituted, or aminocarbonyl, mono [(CrC 4 ) alkylamino] carbonyl, di [(dC 4 ) alkylamino] carbonyl, (Ci-C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (Cι-C) Haloalkylsulfinyl or (Ci-C) haloalkylsulfonyl means, m is an integer 0 or 1, n is an integer 0 or 1 and
0 eiine ganze Zahl 0 oder 1 , bedeuten, wobei die Summe m + n + o eine ganze Zahl 1 , 2 oder 3 ergibt und im Fall der oben definierten Alternativen (b) mindestens einer der Reste R3, R4 und R5 aus Resten aus der Gruppe bestehend aus Wasserstoff und einem Rest der Formel B1, B2 bzw. B3 ausgewählt ist.0 is an integer 0 or 1, where the sum m + n + o is an integer 1, 2 or 3 and, in the case of the alternatives (b) defined above, at least one of the radicals R 3 , R 4 and R 5 Residues from the group consisting of hydrogen and a radical of the formula B 1 , B 2 or B 3 is selected.
15. Verbindungen der Formel (I) oder deren Salze nach Anspruch 14, dadurch gekennzeichnet, dass15. Compounds of formula (I) or their salts according to claim 14, characterized in that
R1 einen Rest der Formel -CO-OR, worinR 1 is a radical of the formula -CO-OR, wherein
R Wasserstoff, (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)CycIoalkyl-(C1-C4)alkyl, Phenyl, Phenyl-(C C4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι -C )al kyl , wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Ci-dJAlkoxy, (d- C4)Haloalkoxy, (d-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, Mono(d-C4)alkylamino, Di(C C4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (CrC )Haloalkyl substituiert ist, bedeutet.R is hydrogen, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl, phenyl, phenyl- (CC 4 ) alkyl, heterocyclyl or heterocyclyl- (-C -C) al kyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (Ci-dJalkoxy , (d- C 4 ) haloalkoxy, (dC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, mono (dC 4 ) alkylamino, di (CC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(-C-C 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (-C-C 4 ) alkyl and (CrC) haloalkyl is substituted.
16. Verbindungen der Formel (I) oder deren Salze nach Anspruch 14, dadurch gekennzeichnet, dass16. Compounds of formula (I) or their salts according to claim 14, characterized in that
R1 einen Rest der Formel -C(=NRa)-OR,R 1 is a radical of the formula -C (= NR a ) -OR,
R (CrC8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl,R (CrC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl,
(C3-C6)Cycloalkyl-(C1-C4)alkyl, Phenyl, Phenyl-(d-C4)alkyl, Heterocyclyl oder HeterocyclyKd-dJalkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (d- C4)Haloalkoxy, (Gι-G4)Alkylthio, (C C4)Alkylsulfinyl, (CrC4)Alkylsulfonyl, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C )Alkoxy]carbonyl und im Falle cyclischer Reste auch (CrC4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder(C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, heterocyclyl or HeterocyclyKd-dJalkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (d- C 4 ) haloalkoxy, (Gι-G 4 ) alkylthio, (CC 4 ) Alkylsulfinyl, (CrC 4 ) alkylsulfonyl, mono (-C-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C) alkoxy] carbonyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, or
(d-C4)Alkanoyl, (CrC4)Haloalkanoyl, [(CrC4)Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(C,-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl bedeutet und(dC 4 ) alkanoyl, (CrC 4 ) haloalkanoyl, [(CrC 4 ) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) alkyl] carbonyl, [phenyl - (-C-C 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] -carbonyl, di [(C, -C 4 ) alkylamino] -carbonyl, (d- C 4 ) alkylsulfinyl, ( dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (d-C 4 ) haloalkylsulfonyl and
Ra Wasserstoff, (Cι-C4)AIkanoyl, (d-C4)Haloalkanoyl, [(C1-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C )alkyl]-carbonyl, [Phenyl-(C1-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl bedeutet.R a is hydrogen, (-C-C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(C 1 -C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι -C) alkyl] carbonyl, [phenyl- (C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl , (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (d- C 4 ) haloalkylsulfonyl.
17. Verbindungen der Formel (I) oder deren Salze nach Anspruch 14, dadurch gekennzeichnet, dass17. Compounds of formula (I) or their salts according to claim 14, characterized in that
R1 einen Rest der Formel -CO-NRcR,R 1 is a radical of the formula -CO-NR c R,
R Wasserstoff, (Cι-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl,R is hydrogen, (-CC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl,
(C3-C6)Cycloalkyl-(C1-C4)alkyl, Phenyl, Phenyl-(C1-C4)alkyl, Heterocyclyl oder(C 3 -C 6 ) cycloalkyl- (C 1 -C 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or
Heterocyclyl-(Cι-C )alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkoxy, (d-Heterocyclyl- (-C-C) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (-C-C 4 ) alkoxy, (d-
C4)Haloalkoxy, (d-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, Mono(CrC4)aIkylamino, Di(d-C4)alkylamino. (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (CrC4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oderC 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, Mono (CrC 4 ) alkylamino, di (dC 4 ) alkylamino. (-C-C 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (Cι-C 4 ) haloalkyl is substituted, or
(d-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(d-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(d-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino3-carbonyl, (C C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (C -C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl und(dC 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(dC 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) alkyl] - carbonyl, [phenyl- (dC 4 ) alkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino3-carbonyl, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl , (C -C 4 ) Haloalkylsulfinyl or (d- C 4 ) Haloalkylsulfonyl and
Rc Wasserstoff, (d-C4)Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkoxy und (d-C4)Alkylthio substituiert ist, oderR c is hydrogen, (dC 4 ) alkyl which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (-C-C 4 ) alkoxy and (dC 4 ) alkylthio, or
(d-C4)Alkanoyl, (C1-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, (Cι-C )Alkylsulfinyl und (Cι-C4)Alkylsulfonyl bedeuten.(dC 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(CC 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, (Cι-C) alkylsulfinyl and (Cι-C 4 ) alkylsulfonyl mean ,
18. Pflanzenschutzmittel, dadurch gekennzeichnet, dass es Verbindungen der Formel (I), wie sie nach einem der Ansprüche 1 bis 6 und 14 bis 17 definiert sind, und Formulierungshilfsmittel enthält.18. Plant protection product, characterized in that it contains compounds of the formula (I) as defined according to one of Claims 1 to 6 and 14 to 17, and formulation auxiliaries.
19. Pflanzenschutzmittel, dadurch gekennzeichnet, dass es Verbindungen der Formel (I), wie sie nach einem der Ansprüche 1 bis 6 und 14 bis 17 definiert sind, und ein oder mehrere Pestizide und gegebenenfalls Formulierungshilfsmittel enthält. 19. Plant protection products, characterized in that it contains compounds of the formula (I) as defined according to one of claims 1 to 6 and 14 to 17, and one or more pesticides and optionally formulation auxiliaries.
EP04721478A 2003-03-26 2004-03-18 Use of aromatic hydroxy compounds as safeners Withdrawn EP1610611A1 (en)

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EA200501466A1 (en) 2006-04-28
CN1764374A (en) 2006-04-26
US20040224844A1 (en) 2004-11-11
AU2004224813A1 (en) 2004-10-07
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