EP1653806A1 - Safener based on aromatic-aliphatic carboxylic acid derivatives - Google Patents

Safener based on aromatic-aliphatic carboxylic acid derivatives

Info

Publication number
EP1653806A1
EP1653806A1 EP04763519A EP04763519A EP1653806A1 EP 1653806 A1 EP1653806 A1 EP 1653806A1 EP 04763519 A EP04763519 A EP 04763519A EP 04763519 A EP04763519 A EP 04763519A EP 1653806 A1 EP1653806 A1 EP 1653806A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
carbonyl
radicals
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.)
Withdrawn
Application number
EP04763519A
Other languages
German (de)
French (fr)
Inventor
Udo Bickers
Lothar Willms
Christopher Rosinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1653806A1 publication Critical patent/EP1653806A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic 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
    • 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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the present invention relates to the field of safeners 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, on the plants mentioned. More particularly, the invention relates to the novel use of certain hydroxyaromatic compounds as safeners and new compounds from this group.
  • US-A-4,808,208 describes the use of phenols such as mono- or dihydroxy-acetophenone or hydroxycinnamic acids and some derivatives of these carboxylic acids as safeners for soybean crops against phytotoxic effects of the herbicide glyphosate (phosphonomethylglycine and its salts).
  • 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 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.
  • Acta Horticulturae 381 (1994) pages 390-397 describes the use of certain derivatives of phenolic compounds such as acetylsalicylic acid to influence plant growth, water uptake and osmotic pressure in plants, and discusses their effect on improving the resistance of plants to various stress factors such as drought.
  • the invention therefore relates to the use of compounds of the formula (I) or their salts,
  • 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 through their specific spatial shape defined possible stereoisomers, 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 be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials ,
  • 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.
  • Metal salts especially alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
  • a hydrocarbon residue is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also 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.
  • hydrocarbon radicals and the special radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton.
  • (-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
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals;
  • Alkenyl means e.g. Vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group, preferably allyl, 1-methylprop-2-en-1-yl, 2- methyl-prop-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-yn-1-yl, but-3-yn-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, bicyclo [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-CyclopentenyI, or 1-CyclohexenyI, 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,
  • a partially or completely hydrogenated heterocyclic radical with 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 be found on the hetero ring atoms, which exist in different oxidation states can occur, for example with N and S.
  • 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 dial
  • cyclic systems are also included with those substituents which are bonded to the ring with a double bond, for. B. with an alkylidene group such as methylidene or Ethylidene or an oxo group, imino group or a substituted imino group are substituted.
  • first substituent level if they contain hydrocarbon-containing constituents, may optionally be further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent level.
  • second substituent level may optionally be further substituted there
  • substituents as defined for the first substituent level.
  • substituent levels are possible.
  • substituted radical preferably only includes one or two substituent levels.
  • Preferred substituents for the substituent levels are, for example, amino, hydroxy, halogen, nitro, cyano, mercapto, carboxy, carbonamide, SF, 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, alkyloalkynylylenyl , Alkylsulfon
  • 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, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy, are preferred or ethoxy, (-CC 4 ) haloalkoxy, nitro and cyano.
  • the substituents methyl, methoxy, fluorine and chlorine are particularly preferred.
  • Substituted amino such as mono- or disubstituted amino means a radical from the group of substituted amino radicals, which are, for example, by one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl are N-substituted; 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; for acyl the following applies. Definition, preferably (-C 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
  • 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 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl , (C- ⁇ -C 4 ) haloalkoxy and nitro is substituted, for example o-, m- and p-TolyJ, 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 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, if appropriate
  • N-substituted iminocarboxylic acids or the rest of carbonic acid monoesters N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamic acids, phosphonic acids, phosphinic acids.
  • acyl means formyl, alkylcarbonyl such as [(C 1 -C 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
  • Phenyl moieties are the substituents mentioned generally above for substituted phenyl.
  • Acyl preferably means an acyl radical in the narrower sense, ie a radical of an organic acid in which the acid group is directly connected to the carbon atom of an organic radical, for example formyl, alkylcarbonyl such as acetyl or [(CrC 4 ) alkyl] carbonyl, phenylcarbonyl , Alkylsulfonyl, alkylsulfinyl and other residues of organic acid
  • radical When a general radical is designated (defined) by "hydrogen”, it means a bonded hydrogen atom.
  • the "yl position" of a radical (e.g. an alkyl radical) denotes its binding site.
  • R 1 denotes a nitrile group (-CN).
  • R is 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- (C 1 -C 12 ) alkyl, phenyl, phenyl- (C ⁇ -C 12 ) alkyl, heterocyclyl or heterocyclyl- (CrC ⁇ 2 ) alkyl, each of the latter 10 residues unsubstituted or by one or more Radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (C ⁇ -C 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalken
  • R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined.
  • Heterocyclyl in the definitions preferably 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, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (d- C 4 ) alkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkyl, (CC 4 ) haloalkoxy, (CC 4 ) alkylthio and oxo.
  • R is hydrogen, (dC 12 ) 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 I phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 4 ) alkyl, each of the last 10 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, (CrC) alkoxy, (d- C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (-C-C 4
  • X is a divalent group 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 direct bond or a divalent 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, and
  • R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined.
  • 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 4 ) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (C ⁇ -C 4 ) alkoxy, (d- C 4 ) haloalkoxy, (CC 4 ) Alkylthio, (dC 4 ) alkyisulfinyl, (dC 4 ) alkylsulfonyl, mono (CrC 4 ) alkylamino, di (dC) alkylamino,
  • R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined.
  • R 1 preferably denotes a radical of the formula -CO-OR, in which
  • 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 ) cycloalkyr- (C 1 -C 4 ) alkyl, phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 4 ) aIkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (i.e.
  • 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- (C ⁇ -C 4 ) alkyl, each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, (-C-C 4 ) alkoxy, (d- C 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 or -CO-O " M + or -CO-OR, in which
  • R (C ⁇ -d) alkyl which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (CrC 4 ) alkoxy and (CC 4 ) alkylthio, and
  • 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 an optionally substituted ammonium ion, preferably NH 4 + or ammonium ions of organic amines or quaternary (quaternary) ammonium ions.
  • R 1 carboxyl and salts thereof, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butoxycarbonyl, isopropoxycarbonyl, (2-hydroxy-ethoxy) carbonyl.
  • R and R a are as defined above, preferably R (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl r (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) Cycloalkyr- (-C-C 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues the group halogen, hydroxy, (dC 4 ) alkoxy, (d-C 4 ) halo!
  • 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, where R and R c are as defined above, preferably
  • R is hydrogen, (C ⁇ -C8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) alkynyl, (C 3 -C 6) cycloalkyl, (C 3 -C 6) cycloalkyl- (C ⁇ - C 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, heterocyclyl or heterocyclyl- (C 1 -C 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (i.e.
  • 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-methylaminocarbonyl, N-acetyl-N-methylaminocarbonyl.
  • R 1 is a radical of the formula -CO-R, wherein
  • 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- (C ⁇ -C 4 ) aIkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 4 ) alkyl, where each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (Ci -dJAlkoxy, (d- C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (C ⁇ -C) alkylamino, di (C 1 -
  • R (d-dJ alkyl means unsubstituted or by one or more
  • Residues from the group halogen, hydroxy, (d-dJalkoxy and, (-C-C 4 ) alkylthio is substituted, and
  • R a is hydrogen or, independently of one another, the radical R is defined above or preferably (-C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(dC) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, phenylcarbonyl , Phenoxycarbonyl, [phenyl- (dC 4 ) alkyI] -carbonyl, [phenyl- (CrC 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(C 1 -C) alkylamino] -carbonyl, di [(C ⁇ -C 4 ) alkylamino] carbonyl, (Cr C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (CC 4 ) haloalkylsulfon
  • R 1 formyl, acetyl, trifluoroacetyl, propionyl, 1-oxobutyl, iminomethyl, 1-imino-ethyl, 1-iminopropyl, N-methyl-iminomethyl, N, N-dimethyl-iminomethyl, N-ethyl-iminomethyl, N, N -Diethyl-iminomethyl, N-methyl-1-iminoethyl, N, N-dimethyl-1-iminoethyl, acetiminomethyl, 1-acetimino-ethyl, 1 -acetiminopropyl, (2-hydroxy-ethoxy) -acetiminomethyl, N-acetyl-iminomethyl , N-acetyl-N-methyl-iminomethyl, N-acetyl-N-ethyl-iminomethyl.
  • iminomethyl 1-imino-ethyl, 1-iminopropyl, N
  • (R 4 ) m m are R 4 radicals, each of the R 4 radicals independently of one another from the group consisting of halogen, SCN, CN and C ⁇ -C18) alkyl, (C 2 -C ⁇ 8) alkenyl, (C 2 -C 18) alkynyl, (C 3 -C 9) cycloalkyl, (C 5 - C 9) cycloalkenyl, (Cs-C ⁇ CycloalkyKd- C ⁇ aikyl, phenyl, phenyl- (d-Ci 2 ) alkyl, heterocyclyl and heterocyclyl- (C ⁇ -C 12 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, Cyano, nitro, thiocyanato, (dC 4 )
  • A is hydrogen or (-CC 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- (CrCi 2 ) alkyl, phenyl, phenyl- (CrC ⁇ 2 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C ⁇ 2 ) alkyl, or preferably (-C-C 12 ) 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 6 ) alkyl, phen
  • R 4 m m radicals R 4 , each of the radicals R 4 independently of one another from the group consisting of halogen, SCN, CN and (dC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) Alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (-C-C 4 ) alkyl, phenyl, phenyl- (CC 4 ) alkyl, heterocyclyl and heterocycIyl- (C ⁇ -C 4 ) alkyl , and preferably-thereby (dC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (CrC 2 ) alkyl,
  • m is the integer 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in particular 0, 1, 2 or 3, very particularly 1 or 2, mean.
  • Heterocyclyl preferably 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, (Ci C 4 ) alkoxy, (dC 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, (dC) alkylthio and oxo.
  • R 4 m m radicals R 4 , each of the radicals R 4 independently of one another from the group consisting of halogen, SCN, CN and (dC) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) Alkynyl and (C 3 -C 6 ) cycloalkyl, each of the latter 4 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio , (dC 4 ) alkylsulfinyl, (d-C 4 ) alkylsulfonyl, (C ⁇ -C 4 ) alkanoyi, (C -C 4 ) haloalkanoyl, [(d-dJalkoxyjcarbonyl and in the case of cyclic radicals also (CrC) al
  • radicals R 4 m rn radicals R 4 , each of the radicals R 4 independently of one another from the group of the radicals halogen, such as F, Cl, Br and I, and SCN, CN and (C ⁇ -d) alkyl, (C 2 - C 4 ) alkenyl, (C 2 -C 4 ) alkynyl and (C 3 -C 6 ) cycloalkyl, each of the latter 4 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, ( C ⁇ -C 4 ) HaloaIkoxy, (dC 4 ) alkylthio, and in the case of cyclic radicals also (dC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, and radicals of the formula -Z * -A is selected, wherein Z * is a group of the formula Q or S (O) x , where x
  • group A-Z * means a hydroxyl group or an acyloxy group, e.g. B. acetyloxy or propionyloxy.
  • R 1 , R 2 , R 3 , R 4 and m are as defined in formula (I).
  • Koxy , (d- C) haloalkoxy, is substituted, and radicals of the formula -Z * -A is selected, where Z * is a group of the formula Q or S and A is hydrogen or (dC 4 ) alkyl, (C 2 -C 4 ) Alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl where each of the latter 4 radicals is unsubstituted or by one or more radicals from the group halogen, hydroxy, (Ci-dJalkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (dC 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(d-dJalkoxyjcarbonyl and in the
  • the compounds of the formula (I) can be prepared analogously to known processes as described for the preparation of cinnamic acids and their derivatives.
  • the acid derivatives such as aldehydes and ketones are likewise obtained in accordance with or analogously to known processes (see reference works and manuals of preparative organic chemistry, for example, Houben Weyl, Organic Synthesis, and the literature cited therein).
  • the invention also relates to the method for protecting crops or useful plants from phytotoxic effects of agrochemicals, such as pesticides or fertilizers, or from environmental factors which cause damage to plants, characterized in that compounds of the formula (I) or their salts are used as Safener applies, preferably an effective amount of the compounds of formula (I) or their salts applied to the plants, parts of the plants or their seeds or seeds thereof.
  • the safeners are suitable, together with agrochemical active substances (pesticides or fertilizers), preferably pesticides for the selective control of Harmful organisms to be used in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, rye, triticale, rice, corn, millet), sugar beet, sugar cane, rapeseed, cotton and soy.
  • agrochemical active substances pesticides or fertilizers
  • pesticides for the selective control of Harmful organisms to be used in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, rye, triticale, rice, corn, millet), sugar beet, sugar cane, rapeseed, cotton and soy.
  • monocotyledon crops such as cereals (wheat, barley, rye, triticale, sorghum), including corn and rice, and monocotyledon vegetable crops, but also in dicotyledon crops
  • Soy crops resistant to herbicidal imidazolinones Soy crops 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.
  • the compounds of the formula (I) according to the invention can be applied simultaneously with the active ingredients or in any order with the active ingredients for agrochemicals / pesticides and are then able to reduce or completely eliminate harmful side effects of these active ingredients in crop plants without the effectiveness of these active ingredients against undesirable harmful organisms or significantly reduce them. Damage caused by the use of several pesticides, e.g. by several herbicides, insecticides or fungicides 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.
  • 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.
  • these agents can be used in the so-called tank mix method - ie immediately before application to the surface to be treated If 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, e.g. for dressing the crop seeds ,
  • 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.
  • the agents according to the invention can contain one or more pesticides.
  • pesticides are herbicides, insecticides, fungicides, acaricides and nematicides, which, when used alone, cause phytotoxic damage to the Crops would result or where 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.
  • 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 application rate of safener can be varied within wide limits depending on the pesticide used and the type of crop to be protected 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 each hectares.
  • 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.
  • 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.
  • the safeners can usually be used separately or together with the agrochemicals, e.g. B. pesticides or fertilizers.
  • the subject is therefore also the crop or crop protection agents.
  • Herbicides whose phytotoxic side effects on crop plants can be reduced by means of compounds of the formula (I) can be used entirely different structure 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 trade names and common names as described in "Compendium of Pesticide Common Names "(can be queried via the Internet) and the literature cited there.
  • 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
  • flufenpyr flumetsuiam; 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 (-isopropylammoni
  • Compounds of formula I which can be reduced 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-pyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylureas, sulfonylaminocarbonyltriazolinones, triazolo-pyrimidinesulfonamide derivatives, s
  • Suitable herbicides which can be combined with the safeners according to the invention are, for example:
  • Phenoxyphenoxy and benzyloxyphenoxy carboxylic acid derivatives e.g. 2- (4-
  • Preferred substituents on the pyrimidine ring or triazine ring are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, where all substituents can be combined independently of one another.
  • Preferred substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl) alkylamino part are alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy, haloalkyl, alkylcarbonyl, alkoxyalkyl, ( alkanesulfonyl) alkylamino.
  • Suitable sulfonylureas are B1) phenyl- and benzylsulfonylureas and related compounds, for example 1- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea (chlorosulfuron ), 1- (2-ethoxycarbonylphenylsulfonyl) -3- (4-chloro-6-methoxypyrimidin-2-yl) urea (chlorimuron-ethyl), 1 - (2-methoxyphenylsulfonyl) -3- (4-methoxy-6-methyl -1, 3,5-triazin-2-yl) urea (metsulfuron-methyl), 1- (2-chloroethoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl ) ham-material (Triasulfur
  • pyrazolylsulfonylureas e.g. 1- (4-EthoxycarbonyI-1-methylpyrazol-5-yI-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (pyrazosulfuron-ethyl);
  • Acetochlor alachlor, butachlor, dimethachlor, dimethenamid, metazachlor,
  • Metolachlor S-metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor and
  • thiocarbamates e.g. S-ethyl-N, N-dipropylthiocarbamate (EPTC), S-ethyl-N, N-diisobutylthiocarbamate (butylates);
  • Cyclohexanedione oximes e.g. Alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, protoxydim, sethoxydim, tepraloxydim and tralkoxydim;
  • imidazolinones e.g. Imazamethabenz-methyl, imazapic, imazamox, imazapyr, imazaquin and imazethapyr;
  • G) triazolopyrimidine sulfonamide derivatives e.g. Chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam and penoxulam;
  • M phosphinic acids and derivatives, e.g. B.
  • N glycine derivatives, e.g. B.
  • S- (N-aryl-N-alkyl-carbamoylmethyl) dithiophosphonic acid esters such as S- [N- (4- Chlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-dimethyl-dithiophosphate (Anilophos);
  • T) pyridinecarboxamides e.g. B. Diflufenican and Picolinafen;
  • Plant growth regulators e.g. B. forchlorfenuron and thidiazuron
  • 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.
  • Fungicidal active ingredients which can be used in combination with the crop protection compounds (I) according to the invention preferably commercially available active ingredients, for example (analogously to the herbicides, the compounds are generally in the form of their "common names" in English
  • epoxiconazole ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-AI; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachlor
  • Insecticides and acaricidal active ingredients are, for example (name analogous to the herbicides and fungicides, if possible as "common names” in English spelling): alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxofuran, carb .
  • Insecticides that can cause plant damage alone or together with herbicides include the following:
  • Organophosphates e.g. Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate (Thimet ® ), Chlorpyriphos (Reldan ® ), Carbamates such as Carbofuran (Furadan ® ), Pyrethroid insecticides such as tefluthrin (Force ® ), deltamethrin (Decis ® ) and tralomethrin (Scout ® ) as well as other insecticidal agents with a different mode of action.
  • Terbufos Counter ®
  • Fonofos Dyfonate ®
  • Phorate Thimet ®
  • Chlorpyriphos Reldan ®
  • Carbamates such as Carbofuran (Furadan ® )
  • Pyrethroid insecticides such as tefluthrin (Force ® ), deltamethrin (Decis ® ) and
  • 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 suitable types of formulation are:
  • 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;
  • Dusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g. Talc, natural clays, like
  • Kaolin 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;
  • Granules such as water-soluble granules, water-dispersible granules and
  • Wettable powders for spreading and soil application; Wettable powders which, in addition to the active substance, also contain diluents or inert substances and surfactants;
  • 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.
  • 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. In emulsifiable concentrates this is Active substance concentration, ie the concentration of safener and / or pesticide, generally 1 to 90, in particular 5 to 80% by weight. 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.
  • the formulations present in the commercial form are optionally diluted in the customary manner, e.g. for 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. With the external conditions such as temperature, humidity, the type of herbicide used u. a. the required application rate of the safener varies.
  • Et ethyl Me methyl n-Pr n-propyl i-Pr isopropyl c-Pr cyclopropyl i-pen isopentyl
  • R 5-Me means methyl in the 5-position on the phenyl ring (see numbering of the ring atoms in the formula (Ia))
  • R H only hydrogen as substituents in positions 5 and 6 on the phenyl
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) or a combination of compound (I) with a pesticide and 9CL parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight . Part of oleoylmethyl tauric acid sodium mixed as a wetting and dispersing agent and ground in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) or a combination of compound (I) with a pesticide with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight. Parts of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to above 277 ° C.) and ground in a attritor to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier ,
  • Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 10 "calcium lignosulfonic acid, 5" sodium lauryl sulfate, Mix 3 "polyvinyl alcohol and 7" kaolin, grind on a pin mill and granulate the powder in a fluidized bed by spraying water as granulating liquid.
  • a pesticide 10 "calcium lignosulfonic acid, 5" sodium lauryl sulfate
  • Mix 3 polyvinyl alcohol and 7" kaolin
  • Water-dispersible granules are also obtained by adding 25 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 5 "2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium Homogenized 2 "oleoylmethyl tauric acid sodium, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50" water on a colloid mill and then comminuted it, then ground it on a bead mill and sprayed the resulting suspension in a spray tower using a single-component nozzle and dried it.
  • a pesticide 5 "2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium Homogenized 2 "oleoylmethyl tauric acid sodium, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50" water on a colloid mill and then comminuted it, then ground it on
  • 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 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 spraying sled using a water application rate of 300 liters per hectare.
  • the safeners were used as 20 percent water-dispersible powders and the herbicide isoxaflutole as an aqueous suspension concentrate (see Table 1.1.1).
  • the pots were placed in a greenhouse under favorable growing conditions.
  • herbicide H1 isoxaflutole Verb. 17 2-hydroxycinnamic acid (see Tab. 1)
  • Verb. 155 2,4-dichlorocinnamic acid (see Tab. 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 approximately 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 the uncovered part of the Applied floor surface.
  • a standard additive based on rapeseed oil methyl ester
  • the safeners and the herbicide foramsulfuron were each used as 20 percent water-dispersible powder (for results see Table 1.2.1).
  • the pots were placed in a greenhouse under favorable growing conditions.
  • ZEAMA Zea mays (maize), variety 'Lorenzo'
  • Herbicide H3 glufosinate ammonium
  • Verb. 17 2-hydroxycinnamic acid
  • Verb. 155 2,4-dichlorocinnamic acid
  • ZEAMA Zea mays (maize) cultivar 'Lorenzo' CHEAL Chenopodium album AMARE Amaranthus retroflexus
  • 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 in so that the required application rates (g-a.i./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.
  • herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were adapted to the required
  • the pots were placed in a greenhouse under favorable growing conditions.
  • herbicide H1 isoxaflutole Verb. 17 2-hydroxycinnamic acid (see Tab. 1)
  • Verb. 155 2,4-dichlorocinnamic acid (see Tab. 1)
  • herbicide H1 isoxaflutole Verb. 17 2-hydroxycinnamic acid (see Tab. 1)
  • Verb. 155 2,4-dichlorocinnamic acid (see Tab. 1)
  • GLXMA Glycine max sibean
  • the herbicides in the form of liquid (for example emulsion concentrates) or dry (for example 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 with 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.
  • a standard additive based on rapeseed oil methyl ester
  • the pots were placed in a greenhouse under favorable growing conditions.
  • herbicide H2 foramsulfuron Verb. 17 2-hydroxycinnamic acid (see Tab. 1)
  • Verb. 155 2,4-dichlorocinnamic acid (see Tab. 1)

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Disclosed are compounds of formula (I) or the salts thereof, wherein R<1> represents COOH or a derivative thereof, preferably a radical of formula -CN, -C(=X)-Y-R, or -C(X'R')(X"R")-Y-R in which R represents H, a (substituted) hydrocarbon radical, heterocyclic radical, or acyl, Y represents a direct bond or O, S, NR<c>, or NR<c>-NR<d>R<e>, and n represents the integer 1, 2, 3, 4, 5, or 6 while R', R", X, X', X", R<a>, R<b>, R<c>, R<d>, R<e>, R<2>, R<3>, (R<4>)m are defined as indicated in claim 1. Said compounds are suitable as safeners for cultivated plants or useful plants in order to counteract phytotoxic effects of agrochemicals, preferably as safeners against the effect of pesticides, such as herbicides, on said plants. Compounds of formula (I) or the salts thereof, wherein R<1> represents COOH, R<2> and R<3> each represent hydrogen, (R<4>)m represents a hydroxy radical (m = 1) in any position or two radicals R<4> (m = 2) in any position, one radical representing a hydroxy group and the other radical representing hydroxy or methoxy in the latter case, and n represents the number 1, are used as safeners for cultivated or useful plants so as to counteract phytotoxic effects of agrochemicals other than glyphosates.

Description

Safener auf Basis aromatisch-aliphatischer CarbonsäurederivateSafener based on aromatic aliphatic carboxylic acid derivatives
Beschreibungdescription
Die vorliegende Erfindung betrifft das Gebiet der Safener 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 an den genannten Pflanzen 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 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, on the plants mentioned. 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 of these carboxylic acids as safeners for soybean crops against 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. 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-A-5,739,080, EP-A- 512737). US-A-4,321 ,084 beschreibt herbizide Mittel mit einem Gehalt an herblziden Thiocarbamaten wie Vernolate oder Butylate in Kombination mit einem AntidotIt 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 the 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. 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-A-5,739,080, EP-A-512737). US-A-4,321,084 describes herbicidal compositions containing herbicidal thiocarbamates such as vernolates or butylates in combination with an antidote
(= Safener) aus der Gruppe einiger 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. WO-A-92/11761 beschreibt Herbizid-Biozid-Antidot-Kombinationen, wobei das Biozid ein Insektizid, Fungizid oder Nematizid bedeuten kann und die Antidots aus der Gruppe strukturell unterschiedlicher Amide, allgemein umfassend auch aromatische Amide, ausgewählt sind, zwecks Vermeidung von "negativem Synergismus " im Zusammenwirken von Herbizid und Biozid. In Acta Horticulturae 381 (1994) Seiten 390-397 wird die Anwendung bestimmter Derivate phenolischer Verbindungen wie Acetylsalicylsäure zur Beeinflussung von Plfanzenwachstum, Wasseraufnahme und osmotischer Druck in Pflanzen beschrieben und deren Wirkung zur Verbesserung der Resistenz der Pflanzen gegen verschiedene Stressfaktoren wie Trockenheit diskutiert.(= Safener) from the group of some 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 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. Acta Horticulturae 381 (1994) pages 390-397 describes the use of certain derivatives of phenolic compounds such as acetylsalicylic acid to influence plant growth, water uptake and osmotic pressure in plants, and discusses their effect on improving the resistance of plants to various stress factors such as drought.
Es wurde nun gefunden, dass überraschenderweise Verbindungen der nachstehend genannten Formel (I) oder deren Salze effektiv als Safener für Kultur- oder Nutzpflanzen gegen Schäden an diesen Pflanzen, die durch strukturell sogar sehr unterschiedliche Agrochemikalien, vorzugsweise aus der Gruppe der selektiven oder nicht-selektiven Herbizide, hervorgerufen werden, eingesetzt werden können. Gegenstand der Erfindung sind auch neue chemische Verbindungen, welche als derartige Safener eingesetzt werden können.It has now been found that, surprisingly, compounds of the formula (I) below or their salts are effective as safeners for culture or Useful plants against damage to these plants, which can be caused by structurally very different agricultural chemicals, preferably from the group of selective or non-selective herbicides. The invention also relates to new chemical compounds which can be used as such safeners.
Ein Gegenstand der Erfindung ist deshalb die Verwendung von Verbindungen der Formel (I) oder deren Salzen,The invention therefore relates to the use of compounds of the formula (I) or their salts,
worin- wherein-
R1 Carboxy oder ein Derivat der Carboxylgruppe, vorzugsweise einen Rest der Formel -CN oder -C(=X)-Y-R oder -C(X'R')(X"R")-Y-R in welcher R Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen heterocyclischen Rest, der unsubstituiert oder substituiert ist, oder Acyl und R', R" jeweils unabhängig voneinander Wasserstoff, (Cι-C6)Alkyl, (C2- C6)Alkenyl, (C2-C6)Alkinyl oder (Cι-C6)Alkanoyl, wobei jeder der letztgenannten 4 Reste im Alkylteil unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (C-ι-C6)Alkoxy und (Cι-C6)Haloalkoxy substituiert ist, oder gemeinsam direkt miteinander gebunden sind und eine divalente Gruppe der Formel -CH2CH2- oder -CH2CH2CH2- oder -CH2CH2CH2CH2-, wobei jeder der letztgenannten 3 Gruppen unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C6)Alkyl, (CrC6)Haloalkyl, (Cι-C6)Alkoxy und (Cι-C6)Haloalkoxy substituiert ist, X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind, X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für Wasserstoff, (C Cβ)Al yl. (C C6)Haloalkyl, (C-i-CβJHydroxyalkyl, (Cι-C )Alkoxy-(CrC4)alkyl [vorzugsweise (C1-C4)Alkoxyalkylj, (C2-C6)Alkenyl oder (C2-C6)Alkinyl steht, Y eine direkte Bindung oder eine Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind, und Ra, Rb, Rc, Rd und Re in den Resten X und Y jeweils unabhängig voneinander und unabhängig vom Rest R (= unabhängig von der jeweiligen Einzelbedeutung -von R) wie für R definiert ist (= wie die allgemeine Definition unter R) oder einen Rest der Formel -OR*, wobei R* unabhängig von R wie für R definiert ist, bedeuten, R2, R3 jeweils unabhängig voneinander und im Falle, dass n = 2, 3, 4, 5 oder 6 bedeutet, jeweils unabhängig von den anderen Resten R2 und R3 Wasserstoff, Halogen, (d-C4)Alkyl, (C2-C4)AlkenyI, (C2-C4)Alkinyl, (d- C )Alkoxy, (CrCδJAlkanoyloxy oder (C C5)Alkanoyl, wobei jeder der letztgenannten 6 Reste unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C6)Alkoxy und (C-ι-C6)Haloalkoxy substituiert ist, (R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN, einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, einen heterocyclischen Rest, der unsubstitutiert oder substitutiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, und A Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen heterocyclischen Rest, der unsubstitutiert oder substitutiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, bedeuten, und m die ganze Zahl 0, 1 , 2, 3, 4 oder 5, vorzugsweise 0, 1 , 2, 3 oder 4, insbesondere 0, 1 , 2 oder 3, ganz besonders 1 oder 2, n die ganze Zahl 1 , 2, 3, 4, 5 oder 6, vorzugsweise 1 , 2 oder 3, insbesondere 1 oder 2, ganz besonders 1 , bedeuten, als Safener für Kultur- oder Nutzpflanzen gegen phytotoxische Wirkungen von Agrochemikalien, vorzugsweise als Safener gegen die Wirkung von Pestiziden, wie Herbiziden, an diesen Pflanzen, wobei Verbindungen der Formel (I) oder deren Salze, .worin R1 Carboxy,R 1 is carboxy or a derivative of the carboxyl group, preferably a radical of the formula -CN or -C (= X) -YR or -C (X'R ') (X "R") - YR in which R is hydrogen or a hydrocarbon radical, which is unsubstituted or substituted, or a heterocyclic radical which is unsubstituted or substituted, or acyl and R ', R "each independently of one another hydrogen, (-CC 6 ) alkyl, (C 2 - C 6 ) alkenyl, (C 2 -C 6 ) alkynyl or (-C-C 6 ) alkanoyl, each of the latter 4 residues in the alkyl part unsubstituted or by one or more residues from the group halogen, hydroxy, (C-ι-C 6 ) alkoxy and (Cι-C 6 ) Haloalkoxy is substituted, or are directly bonded together and a divalent group of the formula -CH 2 CH 2 - or -CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 -, each of the latter 3 Groups unsubstituted or by one or more radicals from the group halogen, hydroxy, (dC 6 ) alkyl, (CrC 6 ) haloalkyl, (-C-C 6 ) alkoxy and (-C-C 6 ) Haloalkoxy is substituted, X is a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, X ', X "each independently divalent group of the formula O, S or NR °, where R ° is hydrogen, (C Cβ) al yl. (CC 6 ) haloalkyl, (Ci-CβJ hydroxyalkyl, (Cι-C) alkoxy- (CrC 4 ) alkyl [preferably ( C 1 -C 4 ) alkoxyalkylj, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, Y is a direct bond or 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, and 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 (= independently of the respective Individual meaning -of R) as defined for R (= as the general definition under R) or a radical of the formula -OR *, where R * is independent of R as defined for R, R 2 , R 3 each independently and in the case that n = 2, 3, 4, 5 or 6 , each independently of the other R 2 and R 3 radicals hydrogen, halogen, (dC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (d- C) alkoxy, (CrC δ JAlkanoyloxy or (CC 5 ) alkanoyl, where each of the latter 6 residues is unsubstituted or substituted by one or more residues from the group halogen, hydroxy, (Cι-C 6 ) alkoxy and (C-ι-C 6 ) haloalkoxy, (R 4 ) m m radicals R 4 , where each of the radicals R 4 independently of one another from the group of the radicals halogen, SCN, CN, a hydrocarbon radical which is unsubstituted or substituted, a heterocyclic radical which is unsubstituted or substituted, and radicals of the formula -Z * -A is selected, where Z * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and A is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclic radical who unsubstituted or is substituted, or an acyl radical, provided that Z * in the case A = acyl can only be O or S, and m is the integer 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2 , 3 or 4, in particular 0, 1, 2 or 3, very particularly 1 or 2, n the integer 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, in particular 1 or 2, very particularly 1, mean as a safener for crops or useful plants against phytotoxic effects of agrochemicals, preferably as a safener against the action of pesticides, such as herbicides, on these plants, where compounds of the formula (I) or their salts, .worin R 1 carboxy,
R2, R3 jeweils Wasserstoff, (R4)m einen Hydroxyrest (m = 1) in beliebiger Position oder zwei Reste R4 (m = 2) in beliebiger Position, wobei in letzterem Fall der eine Rest eine Hydroxygruppe ist und der andere Rest Hydroxy oder Methoxy bedeutet, und n die Zahl 1 bedeuten, als Safener für Kultur- oder Nutzpflanzen gegen phytotoxische Wirkungen von anderen Agrochemikalien als Glyphosate verwendet werden.R 2 , R 3 are each hydrogen, (R 4 ) m is a hydroxy radical (m = 1) in any position or two radicals R 4 (m = 2) in any position, in the latter case one radical being a hydroxyl group and the other The remainder is hydroxy or methoxy, and n is the number 1, are used as safeners for crops or crop plants against phytotoxic effects of agrochemicals other than glyphosate.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die Formel (I) erfasst werden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der Formel (I) umfasst.If the compounds can form tautomers by means of hydrogen shift, which structurally are not 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 through their specific spatial shape defined possible stereoisomers, 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 be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials ,
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 beispielsweiseThe 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
Metallsalze, insbesondere Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quatemäre) Ammoniumsalze.Metal salts, especially alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
In der Formel (I) und allen nachfolgenden Formeln gelten folgende Definitionen:The following definitions apply in formula (I) and all subsequent formulas:
Die mit Wellenlinien gezeichneten ("gewellten") Bindungen in Formel (I) deuten an, dass die Verbindungen als E- und Z-Isomere an den Doppelbindungen der Seitenkette vorliegen können. Die E- und Z-Isomere sind alle von der Formel (I) umfasst. Die Isomere stehen in vielen Fällen miteinander im Gleichgewicht. Bevorzugt sind für die Anwendung die thermodynamisch stabileren Isomere.The (wavy) bonds in formula (I) drawn with wavy lines indicate that the compounds may exist as E and Z isomers on the double bonds of the side chain. The E and Z isomers are all encompassed by formula (I). The isomers are in equilibrium with one another in many cases. The thermodynamically more stable isomers are preferred for use.
Als Derivate der Carboxylgruppe kommen in Ergänzung zu den genannten Gruppen bzw. überlappend beispielsweise in Frage: Aldehydgruppe, Ketogruppe, Estergruppe, Thioestergruppe, Amidgruppe, Hydrazidgruppe, Hydoxamsäuregruppe.As derivatives of the carboxyl group, in addition to the groups mentioned or overlapping, for example: aldehyde group, keto group, ester group, thioester group, amide group, hydrazide group, hydoxamic acid group.
Ein Kohlenwasserstoffrest ist ein aliphatischer, cycloaliphatischer oder aromatischer monocyclischer oder, im Falle eines gegebenenfalls substituierten Kohlenwasserstoffrestes, auch bicyclischer oder polycyclischer organischer Rest auf Basis der Elemente Kohlenstoff und Wasserstoff, beispielsweise umfassend die Reste Alkyl, Alkenyl, Alkinyl, 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 residue is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also 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 further defined, 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 speziellen Reste Alkyl, Alkoxy, Haloalkyl, Haloalkoxy, Alkylamino und Alkylthio sowie die entsprechenden ungesättigten und/oder substituierten Reste können im Kohlenstoffgerüst jeweils geradkettig oder verzweigt sein. 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 undThe hydrocarbon radicals and the special radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and / or substituted radicals can each be straight-chain or branched in the carbon skeleton. 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, 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 group, vorzugsweise Allyl, 1-Methylprop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl,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 e.g. Vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group, 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-Methyi-but-3-en-1-yl oder 1-Methyl-but-2-en-1-yl. (C2-C6)Alkinyl bedeutet beispielsweise Ethinyl, Propargyl, 1-MethyI-2-propinyl, 2-Methyl-2-propinyl, 2-Butinyl, 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.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-yn-1-yl, but-3-yn-1-yl or 1-methyl-but-3 -in-1-yl.
Alkyliden, z. B. auch in der Form (Cι-Cιo)Alkyliden, 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 (-C-Cιo) alkylidene, 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, naturally only positions are possible at which two H atoms can be replaced by the double bond; Leftovers are e.g. B. = CH 2 , = CH-CH 3> = C (CH 3 ) -CH 3> = C (CH 3 ) -C 2 H 5 or = C (C 2 H 5 ) -C 2 H 5 .
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, Bicyclo[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, bicyclo [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-CyclopentenyI, oder 1-CyclohexenyI, 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-CyclopentenyI, or 1-CyclohexenyI, 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 -alkinyl 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 alkynyl mean, through identical 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, CCI 3 , CHCI 2) CH 2 CH 2 CI; 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 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.Also preferred is a partially or completely hydrogenated heterocyclic radical with 2 heteroatoms from the group N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and 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.Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and additionally oxo. The oxo group can also be found on the hetero ring atoms, which exist in different oxidation states can occur, for example with 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 (= TetrahydrofuryJ), 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 (= tetrahydrofuryJ), 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 einer 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., corresponding unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy, etc., are included as substituents in addition to the saturated hydrocarbon-containing radicals mentioned. 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. with an alkylidene group such as methylidene or Ethylidene or an oxo group, imino group or a substituted imino group are substituted.
Die beispielhaft genannten Substituenten ("erste Substituentenebene") können, sofern sie kohlenwasserstoffhaltige 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”), if they contain hydrocarbon-containing constituents, may optionally be 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 beispielsweise Amino, Hydroxy, Halogen, Nitro, Cyano, Mercapto, Carboxy, Carbonamid, SF , 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.Preferred substituents for the substituent levels are, for example, amino, hydroxy, halogen, nitro, cyano, mercapto, carboxy, carbonamide, SF, 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, alkyloalkynylylenyl , 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 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, (C-ι-C )Alkyl, vorzugsweise Methyl oder Ethyl, (Cι-C )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. As a rule, substituents from the group halogen, for example fluorine and chlorine, (C 1 -C 4 ) alkyl, preferably methyl or ethyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy, are preferred or ethoxy, (-CC 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, by one or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl are N-substituted; 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; for acyl the following applies. Definition, preferably (-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, (CrC4)Alkyl, (Cι-C4)Alkoxy, (Cι-C4)Halogenalkyl, (C-ι-C4)Halogenalkoxy und Nitro substituiert ist, z.B. o-, m- und p-TolyJ, 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 4 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl , (C-ι-C 4 ) haloalkoxy and nitro is substituted, for example o-, m- and p-TolyJ, 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, gegebenenfallsAcyl 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, if appropriate
N-substituierten Iminocarbonsäuren oder der Rest von Kohlensäuremonoestern, N-substituierter Carbaminsäure, Sulfonsäuren, Sulfinsäuren, N-substituierter Sulfonamidsäuren, Phosphonsäuren, Phosphinsäuren.N-substituted iminocarboxylic acids or the rest 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 [(C1-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 imFor example, acyl means formyl, alkylcarbonyl such as [(C 1 -C 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
Phenylteil sind die bereits weiter oben allgemein für substituiertes Phenyl erwähnten Substituenten. 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 [(CrC4)Alkyl]-carbonyl, Phenylcarbonyl, Alkylsulfonyl, Alkylsulfinyl und andere Reste von organischen SäurePhenyl moieties are the substituents mentioned generally above for substituted phenyl. Acyl preferably means an acyl radical in the narrower sense, ie a radical of an organic acid in which the acid group is directly connected to the carbon atom of an organic radical, for example formyl, alkylcarbonyl such as acetyl or [(CrC 4 ) alkyl] carbonyl, phenylcarbonyl , Alkylsulfonyl, alkylsulfinyl and other residues of organic acid
Wenn ein allgemeiner Rest mit "Wasserstoff' bezeichnet (definiert) ist, bedeutet dies ein gebundenes Wasserstoffatom. Mit "yl-Position" eines Restes (z. B. eines Alkylrestes) ist dessen Bindungstelle bezeichnet.When a general radical is designated (defined) by "hydrogen", it means a bonded hydrogen atom. The "yl position" of a radical (e.g. an alkyl radical) denotes its binding site.
Im Folgenden werden erfindungsgemäß einsetzbare Verbindungen der Formel (I) und deren Salze auch kurz als "erfindungsgemäße Verbindungen (I)" bezeichnet.In the following, compounds of the 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 besseren Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit ist die erfindungsgemäße Verwendungs von Verbindungen der genannten Formel (I) oder deren Salzen 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.Especially for reasons of better action, better selectivity and / or better producibility, the use according to the invention of compounds of the formula (I) mentioned or their salts is of particular interest, in which individual radicals have one of the preferred meanings already mentioned or mentioned below, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
Von besonderem Interesse ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin R1 eine Nitrilgruppe (-CN) bedeutet.Of 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).
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'R,)(X"R")-Y-R bedeutet, in welcherAlso 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'R , ) (X "R") - YR means in which
R Wasserstoff, (C1-C18)Alkyl, (C2-C18)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl, (C5-C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(C1-C12)alkyl, Phenyl, Phenyl- (Cι-C12)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- C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (d- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl, Mono(CrC4)alkyIamino, Di(CrC4)alkylamino, (Cι-C4)Alkanoyl, (C C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(Cι-C )Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(d-C4)alkylamino]- carbonyl, Di[(C -C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (CrC4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder (d-C6)Alkanoyl, (C C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C )aIkyI]-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, (C C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (Cι-C4)HaloaIkylsulfonyl, wobei R inklusive Substituenten 1 bis 30 C-Atome, vorzugsweise 1 bis 20 C- Atome, insbesondere 1 bis 16 C-Atome aufweist, und/oder R', R" jeweils unabhängig voneinander (Cι-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl oder (Cι-C6)Alkanoyl, wobei jeder der letztgenannten 4 Reste unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C6)Alkoxy und (d-C6)Haloalkoxy substituiert ist, oder gemeinsam direkt miteinander gebunden sind und eine divalente Gruppe der Formel -CH2CH2- oder -CH2CH2CH2- oder -CH2CH2CH2CH2-, wobei jeder der letztgenannten 3 Gruppen unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkyl, (d-C4)Haloalkyl, (d- C4)Alkoxy und (d-d)Haloalkoxy substituiert ist, X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind, X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für Wasserstoff, (C C4)Alkyl, (C C4)Haloalkyl, (C C4)Hydroxyalkyl, (d-C4)Alkoxy-(d-C )alkyl [vorzugsweise (d-C4)Alkoxyalkyl], (C2-C4)Alkenyl oder (C2-C4)Alkinyl steht, Y eine direkte Bindung oder eine divalente Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind, undR is 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- (C 1 -C 12 ) alkyl, phenyl, phenyl- (Cι-C 12 ) alkyl, heterocyclyl or heterocyclyl- (CrCι 2 ) alkyl, each of the latter 10 residues unsubstituted or by one or more Radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (-C-C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkyIamino, di (CrC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (CC 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C) haloalkoxy] carbonyl, aminocarbonyl, mono [(dC 4 ) alkylamino] carbonyl , Di [(C -C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (Cι-C 4 ) haloalkyl is substituted, or (dC 6 ) alkanoyl, (CC 4 ) haloalkanoyl, [( dC 4 ) alkoxy] approx rbonyl, [(-C-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C) aIkyI] -carbonyl, [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, each of the latter 4 residues is unsubstituted or substituted in the phenyl ring, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(Cι-C4) alkylamino] carbonyl, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) Haloalkylsulfinyl or (-C-C 4 ) haloalkylsulfonyl, where R including substituents has 1 to 30 C atoms, preferably 1 to 20 C atoms, in particular 1 to 16 C atoms, and / or R ′, R ″ in each case independently of one another ( Cι-C6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl or (Cι-C6) alkanoyl, wherein each of the latter 4 radicals group unsubstituted or substituted by one or more radicals from the group halogen , Hydroxy, (-C-C 6 ) alkoxy and (dC 6 ) haloalkoxy is substituted, or are bonded together directly and a divalent group of the formula -CH 2 CH 2 - or -CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 -, each of the latter 3 groups being unsubstituted or by one or more Residues from the group halogen, hydroxy, (-CC 4 ) alkyl, (dC 4 ) haloalkyl, (d-C 4 ) alkoxy and (dd) haloalkoxy is substituted, X is a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, X ', X "each independently of one another is a divalent group of the formula O, S or NR °, where R ° is hydrogen, (CC 4 ) alkyl, (CC 4 ) haloalkyl, (CC 4 ) hydroxyalkyl, (d-C4) alkoxy- (dC) alkyl [preferably (dC 4 ) alkoxyalkyl], (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl , Y is a direct bond or a divalent 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, and
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 bedeuten.R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined.
Dabei bedeutet Heterocyclyl in den Definitionen vorzugsweise einen aliphatischen oder aromatischen Heterocyclus 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, Hydroxy, Amino, (d- C4)Alkyl, (d-C4)Alkoxy, (d-C4)Haloalkyl, (C C4)Haloalkoxy, (C C4)Alkylthio und Oxo substituiert ist.Heterocyclyl in the definitions preferably 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, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, (d- C 4 ) alkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkyl, (CC 4 ) haloalkoxy, (CC 4 ) alkylthio and oxo.
Von besonderem Interesse ist auch die erfindungsgemäße Verwendung vonOf particular interest is the use of
Verbindungen der Formel (I) oder deren Salzen, worin R1 einen Rest der Formel -C(=X)-Y-R oder -C(X'R')(X"R")-Y-R bedeutet, in welcherCompounds of the formula (I) or their salts, in which R 1 is a radical of the formula -C (= X) -YR or -C (X'R ') (X "R") - YR, in which
R Wasserstoff, (d-C12)Alkyl, (C2-C12)Alkenyl, (C2-C12)Alkinyl, (C3-C6)Cycloalkyl, (C5-C6)Cycloalkenyl, (C3-C6)Cycloalkyl-(C1-C4)alkylI 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, (CrC )Alkoxy, (d- C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (Cι-C4)AlkyIsulfinyl, (C C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)HaloalkyIsulfonyl, Mono(Cι-C4)alkylamino, Di(d-C4)alkylamino, (Cι-C4)Alkanoyl, (d-C )Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(CrC4)HaloaIkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C )alkyIamino]- carbonyl, Di[(d-C )alkylamino]-carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder (d-C4)AIkanoyl, (d-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(d-dJHaloalkoxyjcarbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(d-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl,R is hydrogen, (dC 12 ) 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 I phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (Cι-C 4 ) alkyl, each of the last 10 radicals being unsubstituted or by one or more radicals from the group halogen, hydroxy, (CrC) alkoxy, (d- C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (-C-C 4 ) AlkyIsulfinyl, (CC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkyIsulfonyl, mono (Cι-C4) alkylamino, di (dC 4 ) alkylamino, (Cι-C 4 ) alkanoyl , (dC) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C) alkyIamino] carbonyl, di [(dC) alkylamino] carbonyl and in the case cyclic radicals are also substituted (dC 4 ) alkyl and (dC 4 ) haloalkyl, or (dC 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(d-dJHaloalkoxyjcarbonyl, phenylcarbonyl, phenoxycarbonyl, [ Phenyl- (-C-C 4 ) alkyl] -carbonyl, [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(dC 4 ) alkylamino] -carbonyl, (d- C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (d- C 4 ) haloalkylsulfonyl,
X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind,X is a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below,
X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für Wasserstoff, (d-C4)Alkyl, (d-C4)Haloalkyl, (d- C4)HydroxyalkyI, (C2-C4)Alkenyl oder (C2-C4)Alkinyl steht,X ', X "each independently represent a divalent group of the formula O, S or NR °, where R ° is hydrogen, (dC 4 ) alkyl, (dC 4 ) haloalkyl, (d- C 4 ) hydroxyalkyl, (C 2 - C 4 ) alkenyl or (C 2 -C 4 ) alkynyl,
Y eine direkte Bindung oder eine divalente Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind, undY is a direct bond or a divalent 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, and
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, bedeuten.R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined.
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 oder -C(X,R')(X"R")-Y-R, vorzugsweise der Formel -C(=X)-Y-R bedeutet, in welcherR 1 is a radical of the formula -C (= X) -YR or -C (X , R ') (X "R") - YR, preferably of the formula -C (= X) -YR, in which
R Wasserstoff, (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(C1-C4)alkyl, Phenyl, Phenyl-(C C4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-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, (C C4)Alkylthio, (d-C4)AlkyIsulfinyl, (d-C4)Alkylsulfonyl, Mono(CrC4)alkylamino, Di(d-C )alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (CrC4)Alkyl und (d-C )Haloalkyl substituiert ist, oder (d-C4)Alkanoyl, (C C4)Haloalkanoyl, [(C1-C4)Alkoxy]carbonyI, [(d-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(Cι-C )alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (d- C )Haloalkylsulfonyl, X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind, X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für (d-C4)Alkyl steht, Y eine direkte Bindung oder eine divalente Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind, undR 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- (Cι-C 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, (CC 4 ) Alkylthio, (dC 4 ) alkyisulfinyl, (dC 4 ) alkylsulfonyl, mono (CrC 4 ) alkylamino, di (dC) alkylamino, (Cι-C 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (dC) haloalkyl is substituted, or (dC 4 ) alkanoyl, (CC 4 ) haloalkanoyl, [(C 1 -C 4 ) alkoxy] carbonyI, [(dC 4 ) Haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) alkyl] -carbonyl, [phenyl- (Cι-C) 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) haloalkylsulfonyl, X is a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, X ', X "each independently divalent group of the formula O, S or NR °, where R ° is (dC 4 ) alkyl, Y is a direct bond or a divalent 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, and
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, bedeuten.R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined.
Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin R1 einen Rest der Formel -CO-OR oder -C(=NRa)-OR oder -CO-NRcR oder -CO-R oder -C(=NRa)-R bedeutet, wobei R, Ra und Rb wie oben definiert sind.Particular preference is given to 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 -CO-OR or -C (= NR a ) -OR or -CO-NR c R or -CO-R or -C (= NR a ) -R means, where R, R a and R b are as defined above.
Vorzugsweise bedeutet R1 einen Rest der Formel -CO-OR, worinR 1 preferably denotes a radical of the formula -CO-OR, in which
R Wasserstoff, (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)CycloaIkyr-(C1-C4)alkyl, Phenyl, Phenyl-(Cι-C4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)aIkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-dJAlkoxy, (d- C4)Haloalkoxy, (d-C4)Alkylthio, (C1-C4)Alkylsulfinyl, (C1-C4)Alkylsulfonyl, Mono(d-C4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C )Alkanoyl, (Cι-d)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle. cyclischer Reste auch (d-C4)Alkyl und (Cι-d)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 ) cycloalkyr- (C 1 -C 4 ) alkyl, phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (Cι-C 4 ) aIkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (i.e. -dJAlkoxy, (d- C 4 ) haloalkoxy, (dC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, mono (d-C4) alkylamino, di (Cι-C 4 ) alkylamino, (-C-C) alkanoyl, (Cι-d) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (Cι-d) haloalkyl is substituted, and in particular
R Wasserstoff, (d-C6)AIkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, oder (C3-C6)Cycloalkyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkoxy, (d- C4)Alkylthio und im Falle cyclischer Reste auch (d-C4)Alkyl substituiert ist, bedeutet.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- (Cι-C 4 ) alkyl, each of the last 5 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, (-C-C 4 ) alkoxy, (d- C 4 ) alkylthio and in the case of cyclic radicals also (dC 4 ) alkyl is substituted.
Ganz besonders ist dabei R1 ein Rest der Formel -CO-OH oder -CO-O" M+ oder -CO-OR, worinR 1 is very particularly a radical of the formula -CO-OH or -CO-O " M + or -CO-OR, in which
R (Cι-d)Alkyl bedeutet, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (CrC4)Alkoxy und, (C C4)Alkylthio substituiert ist, undR (Cι-d) alkyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (CrC 4 ) alkoxy and (CC 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 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- Propoxycarbonyl, n-Butoxycarbonyl, Isopropoxycarbonyl, (2-Hydroxy-ethoxy)- carbonyl.R 1 = carboxyl and salts thereof, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butoxycarbonyl, isopropoxycarbonyl, (2-hydroxy-ethoxy) carbonyl.
Vorzugsweise bedeutet R1 auch einen Rest der Formel -C(=NRa)-OR, worinR 1 preferably also denotes a radical of the formula -C (= NR a ) -OR, in which
R und Ra wie oben definiert sind, vorzugsweise R (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinylr (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyr-(Cι-C4)alkyl, Phenyl, Phenyl-(C1-C4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (d- C4)Haloa!koxy, (C C4)Alkylthio, (d-C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (C1-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder (d-C )Alkanoyl, (CrC )Haloalkanoyl, [(C1-C4)Alkoxy]carbonyl, [(d-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(d-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkyIamino]-carbonyl, Di[(Cι-C )alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsuϊfinyl oder (d- C )Haloalkylsulfonyl, bedeutet und Ra Wasserstoff bedeutet oder unabhängig voneinander wie vorstehend der Rest R definiert ist oder vorzugsweise (Cι-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (Cr C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (C C )Haloalkylsulfonyl bedeutet.R and R a are as defined above, preferably R (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl r (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) Cycloalkyr- (-C-C 4 ) alkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or heterocyclyl- (Cι-C 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues the group halogen, hydroxy, (dC 4 ) alkoxy, (d-C 4 ) halo! koxy, (CC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, mono (Cι-C 4 ) alkylamino , Di (-C-C 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(Cι-C4) alkoxy] carbonyl and in the case of cyclic radicals also (Cι-C 4 ) alkyl and (Cι-C4) haloalkyl, or (dC) alkanoyl, (CrC) haloalkanoyl, [(C 1 -C 4) alkoxy] carbonyl, [(dC 4) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- ( -C-C 4 ) alkyl] -carbonyl, [phenyl- (dC 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkyIamino] -carbonyl, di [(Cι-C) alkylamino] -carbonyl, ( d- C 4 ) alkylsulfinyl, (dC 4 ) Alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (d- C) haloalkylsulfonyl, and R a is hydrogen or, independently of one another, the radical R is as defined above or preferably (-C-C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [( dC 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl (C 1 -C 4 ) alkyl] carbonyl, [phenyl (CrC4) alkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] -carbonyl, di [(-C-C4) alkylamino] carbonyl, (Cr C 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (CC) haloalkylsulfonyl.
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, vorzugsweiseR 1 preferably also denotes a radical of the formula -CO-NR c R, where R and R c are as defined above, preferably
R Wasserstoff, (Cι-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(Cι-C4)alkyl, Phenyl, Phenyl-(d-C4)alkyl, Heterocyclyl oder Heterocyclyl-(C1-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-dJAlkoxy, (d- C4)HaIoalkoxy, (C1-C4)Alkylthio, (C C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (CrC )Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder (Cι-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(Cι-C4)AIkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)aIkyl]-carbonyl, [Phenyl-(C1-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(CrC )alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl oder (d- C4)HaloalkylsuIfonyl, bedeutet und Rc Wasserstoff bedeutet oder unabhängig voneinander wie vorstehend der Rest R definiert ist oder vorzugsweise Rc Wasserstoff, (d-C )Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (C -C4)AlkyIthio, substituiert ist, oder (Cι-C4)Alkanoyl, (d-C4)HaloaIkanoyl, [(d-C4)AIkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, (C1-C4)Alkylsulfinyl oder (d-C4)Alkylsulfonyl oder insbesondere Wasserstoff oder (Cι-d)Alkyl bedeutet.R is hydrogen, (Cι-C8) 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- (dC 4 ) alkyl, heterocyclyl or heterocyclyl- (C 1 -C 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (i.e. -dJAlkoxy, (d- C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (C 1 -C 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(C 1 -C 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (CrC) alkyl and (C 1 -C 4 ) haloalkyl is substituted, or (Cι -C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C 4 ) aIkyl] - carbonyl, [phenyl- (C 1 -C 4 ) alkoxy] carbonyl, aminocarbonyl, mono [(CrC) alkylamino] carbonyl, di [(Cι-C4) alkylamino] carbonyl, (d- C 4 ) alkylsulfinyl, ( CC 4 ) alkylsulfonyl, (CC 4 ) haloalky Isulfinyl or (d- C 4 ) haloalkylsulfonyl, means and R c is hydrogen or, independently of one another, the radical R is defined above or preferably R c is hydrogen, (dC) alkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, (dC 4 ) alkoxy, (C -C 4 ) AlkyIthio, is substituted, or (-C-C 4 ) alkanoyl, (dC 4 ) HaloaIkanoyl, [(dC 4 ) alkoxy] carbonyl, [(-C-C 4 ) haloalkoxy] carbonyl, (C 1 -C 4 ) alkylsulfinyl or (dC 4 ) alkylsulfonyl or in particular hydrogen or (-CC) 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-methylaminocarbonyl, N-acetyl-N-methylaminocarbonyl.
Vorzugsweise bedeutetPreferably means
R1 einen Rest der Formel -CO-R, worinR 1 is a radical of the formula -CO-R, wherein
R Wasserstoff, (C C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(Cι-C4)aIkyl, Phenyl, Phenyl-(C1-C4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Ci-dJAlkoxy, (d- C4)Haloalkoxy, (C C4)AIkylthio, (C1-C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, Mono(Cι-C )alkylamino, Di(C1-C4)alkylamino, (C1-C4)Alkanoyl, (CrC4)HaloalkanoyI, [(CrC4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (d-d)Alkyl und (d-C4)HaloaIkyl substituiert ist, und insbesondere R Wasserstoff, (C C6)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)CycIoalkyl, oder (C3-C6)Cycloalkyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 5 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (d- dJAlkylthio und im Falle cyclischer Reste auch (Cι-C4)Alkyl substituiert ist, bedeutet.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- (Cι-C 4 ) aIkyl, phenyl, phenyl- (C 1 -C 4 ) alkyl, heterocyclyl or heterocyclyl- (Cι-C 4 ) alkyl, where each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (Ci -dJAlkoxy, (d- C 4 ) haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (Cι-C) alkylamino, di (C 1 -C 4 ) alkylamino, (C 1 -C 4 ) alkanoyl, (CrC 4 ) haloalkanoyI, [(CrC4) alkoxy] carbonyl and in the case of cyclic radicals also (dd) alkyl and (dC 4 ) haloalkyl is substituted, and in particular R is hydrogen, (CC 6 ) Alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, or (C 3 -C 6 ) cycloalkyl- (-C-C 4 ) alkyl, each of the latter 5 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, (d-dJ alkylthio and im In the case of cyclic radicals also (-CC 4 ) alkyl is substituted.
Ganz besonders ist dabei R1 ein Rest der Formel CHO oder C(=NRa)-H oder CO-R oder C(=NRa)-R worinR 1 is very particularly a radical of the formula CHO or C (= NR a ) -H or CO-R or C (= NR a ) -R wherein
R (d-dJAlkyl bedeutet, das unsubstituiertoder durch einen oder mehrereR (d-dJ alkyl means unsubstituted or by one or more
Reste aus der Gruppe Halogen, Hydroxy, (d-dJAlkoxy und, (Cι-C4)Alkylthio substituiert ist, undResidues from the group halogen, hydroxy, (d-dJalkoxy and, (-C-C 4 ) alkylthio is substituted, and
Ra Wasserstoff bedeutet oder unabhängig voneinander wie vorstehend der Rest R definiert ist oder vorzugsweise (Cι-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(d-C )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (d-C4)alkyI]-carbonyl, [Phenyl-(CrC4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(C1-C )alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (Cr C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)HaloaIkylsulfinyl oder (C C4)Haloalkylsulfonyl bedeutet.R a is hydrogen or, independently of one another, the radical R is defined above or preferably (-C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(dC) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, phenylcarbonyl , Phenoxycarbonyl, [phenyl- (dC 4 ) alkyI] -carbonyl, [phenyl- (CrC 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(C 1 -C) alkylamino] -carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl, (Cr C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (CC 4 ) haloalkylsulfonyl.
Beispiele für solche Reste sind:Examples of such residues are:
R1 = Formyl, Acetyl, Trifluoracetyl, Propionyl, 1-Oxobutyl, Iminomethyl, 1-lmino- ethyl, 1-lminopropyl, N-Methyl-iminomethyl, N,N-DimethyI-iminomethyl,N- Ethyl-iminomethyl, N,N-Diethyl-iminomethyl, N-Methyl-1-iminoethyl, N,N- Dimethyl-1-iminoethyl, acetiminomethyl, 1-acetimino-ethyl, 1 -acetiminopropyl, (2-Hydroxy-ethoxy)-acetiminomethyl, N-Acetyl-iminomethyl, N-Acetyl-N- methyl-iminomethyl, N-Acetyl-N-ethyl-iminomethyl. Von besonderem Interesse ist auch die erfindungsgemäße Verwendung vonR 1 = formyl, acetyl, trifluoroacetyl, propionyl, 1-oxobutyl, iminomethyl, 1-imino-ethyl, 1-iminopropyl, N-methyl-iminomethyl, N, N-dimethyl-iminomethyl, N-ethyl-iminomethyl, N, N -Diethyl-iminomethyl, N-methyl-1-iminoethyl, N, N-dimethyl-1-iminoethyl, acetiminomethyl, 1-acetimino-ethyl, 1 -acetiminopropyl, (2-hydroxy-ethoxy) -acetiminomethyl, N-acetyl-iminomethyl , N-acetyl-N-methyl-iminomethyl, N-acetyl-N-ethyl-iminomethyl. Of particular interest is the use of
Verbindungen der Formel (I) oder deren Salzen, worinCompounds of formula (I) or their salts, wherein
R2, R3 jeweils unabhängig voneinander und im Falle, dass n = 2, 3, 4, 5 oder 6 bedeutet, jeweils unabhängig von den anderen Resten R2 und R3 Wasserstoff, (d-C2)Alkyl, (d-C2)Alkoxy oder (Cι-C3)Alkanoyloxy, wobei jeder der letztgenannte 3 Reste im Alkylteil unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C6)Alkoxy und (d- C6)Haloalkoxy substituiert ist, vorzugsweise Wasserstoff, Methyl oder Ethyl, insbesondere Wasserstoff, und n 1 , 2, 3, 4, 5 oder 6, vorzugsweise 1 , 2 oder 3, insbesondere 1 oder 2, ganz besonders 1 , bedeuten.R 2 , R 3 are each independently of one another and in the case where n = 2, 3, 4, 5 or 6, in each case independently of the other radicals R 2 and R 3 is hydrogen, (dC 2 ) alkyl, (dC 2 ) alkoxy or (-C-C 3 ) alkanoyloxy, where each of the latter 3 residues in the alkyl part is unsubstituted or substituted by one or more residues from the group halogen, hydroxy, (-C-C 6 ) alkoxy and (d- C 6 ) haloalkoxy, preferably Is hydrogen, methyl or ethyl, in particular hydrogen, and n is 1, 2, 3, 4, 5 or 6, preferably 1, 2 or 3, in particular 1 or 2, very particularly 1.
Von besonderem Interesse ist auch die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin (R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN und (Cι-C18)Alkyl, (C2-Cι8)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl, (C5- C9)Cycloalkenyl, (Cs-C^CycloalkyKd-C^aikyl, Phenyl, Phenyl-(d-Ci2)alkyl, Heterocyclyl und Heterocyclyl-(Cι-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-C4)Alkoxy, (d-dJHaloalkoxy, (C2- C4)Alkenyloxy, (C2-C4)Haloalkenyioxy, (Cι-C4)AlkyIthio, (d- C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl, Mono(Cι-C4)alkylamino, Di(d-C4)alkylamino, (C C4)Alkanoyl, (d-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]- carbonyl, Di[(Cι-C4)alkyIamino]-carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Cι-C4)HaloalkyI substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobeiAlso of particular interest is the use according to the invention of compounds of the formula (I) or their salts, in which (R 4 ) m m are R 4 radicals, each of the R 4 radicals independently of one another from the group consisting of halogen, SCN, CN and Cι-C18) alkyl, (C 2 -Cι 8) alkenyl, (C 2 -C 18) alkynyl, (C 3 -C 9) cycloalkyl, (C 5 - C 9) cycloalkenyl, (Cs-C ^ CycloalkyKd- C ^ aikyl, phenyl, phenyl- (d-Ci 2 ) alkyl, heterocyclyl and heterocyclyl- (Cι-C 12 ) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, Cyano, nitro, thiocyanato, (dC 4 ) alkoxy, (d-dJHaloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyioxy, (Cι-C 4 ) alkyIthio, (d- C 4 ) alkylsulfinyl , (CC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (Cι-C 4 ) alkylamino, di (dC 4 ) alkylamino, (CC 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [ (dC 4 ) alkoxy] carbonyl, [(-C-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylami no] - carbonyl, di [(C 1 -C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (C 1 -C 4 ) haloalkyI is substituted, and radicals of the formula -Z * -A is selected . in which
Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, undZ * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and
A Wasserstoff oder (Cι-C18)Alkyl, (C2-C18)Alkenyl, (C2-C18)AIkinyl, (C3-C9)CycloaIkyl, (C5- C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(CrCi2)alkyl, Phenyl, Phenyl- (CrCι2)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-Cι2)alkyl, oder dabei vorzugsweise (Cι-C12)Alkyl, (C2-Cι2)Alkenyl, (C2-Cι2)Alkinyl, (C3-C6)Cycloalkyl, (C5-C6)CycloaIkenyl, (C3-C6)Cycloalkyl-(d-C6)alkyl, Phenyl, PhenyI-(Cι-C6)alkyl, Heterocyclyl oder Heterocyclyl- (d-C6)alkyl, wobei jeder der letztgenannten 20 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro7 Thiocyanato, (d-C )Alkoxy, (d-C4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C )Haloalkenyloxy, (C1-C4)Alkylthio, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C )Haloalkylsulfonyl, Mono(Cι-C )alkylamino, Di(Cι-C )aIkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(C C4)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-dJHaloalkyl substituiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, vorzugsweise einen Acylrest aus der Gruppe, die aus den Resten (d-Ce)Alkanoyl, (Cι-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl-(Cι-C4)alkyl]-carbonyl, [Phenyl-(C1-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(Cι-C )alkylamino]-carbonyl, Di[(d-C4)alkylamino]-carbonyl, (Cι-C4)AlkyIsulfinyl, (d- C4)Alkylsulfonyl, (CrC )Haloalkylsulfinyl und (Cι-C4)Haloalkylsulfonyl besteht, bedeuten, wobei jeder Rest R4 inklusive Substituenten 1 bis 30 C-Atome, vorzugsweise 1 bis 20 C-Atome, insbesondere 1 bis 16 C-atome aufweist, und m die ganze Zahl 0, 1 , 2, 3, 4 oder 5, vorzugsweise 0, 1 , 2, 3 oder 4, insbesondere 0, 1 , 2 oder 3, ganz besonders 1 oder 2, bedeuten.A is hydrogen or (-CC 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- (CrCi 2 ) alkyl, phenyl, phenyl- (CrCι 2 ) alkyl, heterocyclyl or heterocyclyl- (Cι-Cι 2 ) alkyl, or preferably (-C-C 12 ) alkyl, (C 2 -Cι 2 ) alkenyl, (C 2 -C 2 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) cycloalkyl- (dC 6 ) alkyl, phenyl, phenyl, (-C-C 6 ) alkyl, heterocyclyl or heterocyclyl- (dC 6 ) alkyl, each of the latter 20 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro 7 thiocyanato, (dC) alkoxy , (dC 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C) haloalkenyloxy, (C 1 -C 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) Haloalkylsulfinyl, (d- C) haloalkylsulfonyl, mono (-C-C) alkylamino, di (Cι-C) aIkylamino, (Cι-C 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(CC 4 ) 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 (Cι-d) alkyl and (d-dJHaloalkyl is substituted, or an acyl radical, provided that Z * in the case of A = acyl can only be O or S, preferably an acyl group from the group consisting of (d-Ce) alkanoyl, (-C-C 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(Cι-C4) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (Cι-C4) alkyl] -carbonyl, [phenyl- (C 1 -C 4) alkoxy] carbonyl, where each of the latter 4 radicals in the phenyl ring is unsubstituted or substituted, aminocarbonyl, mono [(Cι-C) alkylamino] carbonyl, di [(dC 4 ) alkylamino] carbonyl, (Cι-C 4 ) alkyIsulfinyl, (d- C 4 ) alkylsulfonyl, (CrC) haloalkylsulfinyl and (-C-C 4 ) haloalkylsulfonyl, mean where each radical R 4 including substituents has 1 to 30 C atoms, preferably 1 to 20 C atoms, in particular 1 to 16 C atoms, and m is the integer 0, 1, 2, 3, 4 or 5, preferably 0 , 1, 2, 3 or 4, in particular 0, 1, 2 or 3, very particularly 1 or 2, mean.
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
(R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN und (d-C6)Alkyl, (C2-C6)AIkenyl, (C2-C6)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(Cι-C4)alkyl, Phenyl, Phenyl-(C C4)alkyl, Heterocyclyl und HeterocycIyl-(Cι-C4)alkyl, und vorzugsweise-dabei (d-C4)Alkyl, (C2- C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl, (C3-C6)Cyclöalkyl-(CrC2)alkyl, Phenyl, Phenyl-(d-C2)alkyl, Heterocyclyl und Heterocyclyl-(d-C2)alkyl, wobei jeder der letztgenannten 18 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, (d-C4)Alkoxy, (C C4)Haloalkoxy, (C2-C )Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (Cι-C4)Alkylsulfinyl, (d- C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (C1-C4)Haloalkylsulfonyl, Mono(CrC4)alkylamino, Di(Cι-C4)alkyIamino, (d-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(d-C )alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (CrC4)Alkyl und (d-C4)Haloalkyl substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, und A Wasserstoff oder (d-C8)Alkyl, (C2-C8)Alkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C5- C6)Cycloalkenyl, (C3-C6)Cycloalkyl-(C1-C6)alkyl, Phenyl, Phenyl- (CrCβJalkyl, Heterocyclyl oder Heterocyclyl-(C C6)alkyl, oder vorzugsweise dabei (Cι-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C4)Cycloalkyl, (C3-C6)Cycloalkyl-(d-C4)aIkyl, Phenyl, Phenyl- (CrC4)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C4)alkyl, wobei jeder der letztgenannten 19 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxyr Amino, Cyano, Nitro, Thiocyanato, (Cι-d)AI koxy, (d-C )Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C1-C4)Alkylthio, (C C4)AlkylsuIfinyl, (d-C4)Alkylsulfonyl, (d-C4)HaloalkylsulfinyI, (d- C4)Haloalkylsulfonyl, Mono(Cι-C4)alkylamino, Di(CrC4)alkylamino, (Cι-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(Cι-C )Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(CrC4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)AlkyLund (Cι-C4)Haloalkyl substituiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, vorzugsweise einen Acylrest aus der Gruppe, die aus den Resten (d-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(C1-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl-(Cι-C4)alkyl]-carbonyl, [Phenyl-(C1-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, (d- C4)Alkyl, (d-C4)Alkoxy, (d-C4)Haloalkyl, (C C4)Haloalkoxy und (d- dJAlkylthio substituiert ist, besteht, bedeuten, und m die ganze Zahl 0, 1 , 2, 3, 4 oder 5, vorzugsweise 0, 1 , 2, 3 oder 4, insbesondere 0, 1 , 2 oder 3, ganz besonders 1 oder 2, bedeuten.(R 4 ) m m radicals R 4 , each of the radicals R 4 independently of one another from the group consisting of halogen, SCN, CN and (dC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) Alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (-C-C 4 ) alkyl, phenyl, phenyl- (CC 4 ) alkyl, heterocyclyl and heterocycIyl- (Cι-C 4 ) alkyl , and preferably-thereby (dC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (CrC 2 ) alkyl, phenyl, phenyl- (dC 2 ) alkyl, heterocyclyl and heterocyclyl- (dC 2 ) alkyl, each of the latter 18 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, ( dC 4 ) alkoxy, (CC 4 ) haloalkoxy, (C 2 -C) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (Cι-C 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (C 1 -C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (Cι-C 4 ) alkyIamino, (dC 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C ) Alkoxy] carbonyl, [(-C-C 4 ) H aloalkoxy] carbonyl, aminocarbonyl, mono [(dC) alkylamino] carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, and radicals of the formula -Z * -A is selected, where Z * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and A is hydrogen or (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 - C 6 ) cycloalkenyl, (C 3 -C 6 ) cycloalkyl- (C 1 -C 6 ) alkyl, phenyl , Phenyl- (CrCβJalkyl, heterocyclyl or heterocyclyl- (CC 6 ) alkyl, or preferably (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 4 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (dC 4 ) aIkyl, phenyl, phenyl- (CrC 4 ) alkyl, heterocyclyl or heterocyclyl- (-C-C 4 ) alkyl, each of the latter 19 residues unsubstituted or by one or more residues from the group halogen, hydroxy r amino, cyano, nitro, Thiocyanato, (Cι-d) AI koxy, (dC) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (C 1 -C 4 ) alkylthio, (CC 4 ) alkylsulifinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyI, (d- C 4 ) haloalkylsulfonyl, mono (-C-C 4 ) alkylamino, di (CrC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [( CC 4 ) alkoxy] carbonyl, [(-C-C) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(CrC 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (Cι -C 4 ) AlkyLund (-C-C 4 ) haloalkyl, or an acyl radical, provided that Z * in the case A = acyl can only be O or S, preferably a en acyl radical from the group consisting of the radicals (dC 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(C 1 -C 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [ Phenyl- (-C-C 4 ) alkyl] -carbonyl, [phenyl- (C 1 -C 4 ) alkoxy] -carbonyl, each of the latter 4 radicals in the phenyl ring being unsubstituted or by one or more radicals from the group halogen, (i.e. - C 4 ) alkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkyl, (CC 4 ) haloalkoxy and (d-dJ alkylthio), is, mean, and m is the integer 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4, in particular 0, 1, 2 or 3, very particularly 1 or 2, mean.
Dabei bedeutet Heterocyclyl vorzugsweise 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)Alkyl, (Ci- C4)Alkoxy, (d-C4)Haloalkyl, (C1-C4)HaloaIkoxy, (d-C )Alkylthio und Oxo substituiert ist.Heterocyclyl preferably 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, (Ci C 4 ) alkoxy, (dC 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, (dC) alkylthio and oxo.
Weiter bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worinThe use according to the invention of compounds of the formula (I) or their salts, in which
(R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN und (d-C )Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl und (C3-C6)Cycloalkyl, wobei jeder der letztgenannten 4 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, (Cι-C4)Alkanoyi, (C -C4)Haloalkanoyl, [(d-dJAlkoxyjcarbonyl und im Falle cyclischer Reste auch (CrC )AlkyI und (d-C4)Haloalkyl" substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, und A Wasserstoff oder (Cι-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-dJAlkoxy, (Cι-C4)Haloalkoxy, (d-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d- C4)Alkylsulfonyl, (d-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl und im Falle cyclischer Reste auch (CrC )Alkyl und (d-C4)Haloalkyl substituiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, vorzugsweise einen Acylrest aus der Gruppe, die aus den Resten (Cι-d)Alkanoyl, (C1-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(d-C4)Haloalkoxy]carbonyl besteht, bedeuten, bedeutet. Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I) oder deren Salzen, worin(R 4 ) m m radicals R 4 , each of the radicals R 4 independently of one another from the group consisting of halogen, SCN, CN and (dC) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) Alkynyl and (C 3 -C 6 ) cycloalkyl, each of the latter 4 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (-C-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio , (dC 4 ) alkylsulfinyl, (d-C 4 ) alkylsulfonyl, (Cι-C 4 ) alkanoyi, (C -C 4 ) haloalkanoyl, [(d-dJalkoxyjcarbonyl and in the case of cyclic radicals also (CrC) alkyI and (dC 4 ) Haloalkyl " , and radicals of the formula -Z * -A is selected, where Z * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and A is hydrogen or (-Cι- C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl where each of the latter 4 residues is unsubstituted or by one or more residues from the group halogen, hydroxy , (d-dJAlkoxy, (-C-C 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (d- C 4 ) Alkylsulfonyl, (dC 4 ) alkanoyl, (-C-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl and in the case of cyclic radicals also (CrC) alkyl and (dC 4 ) haloalkyl is substituted, or an acyl radical, provided that Z * in the case of A = acyl can only be O or S, preferably an acyl radical from the group consisting of the (Cι-d) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(Cι-C 4 ) Alkoxy] carbonyl, [(dC 4 ) haloalkoxy] carbonyl, means. The use according to the invention of compounds of the formula (I) or their salts, in which
(R4)m rn Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, wie F, Cl, Br und I, und SCN, CN und (Cι-d)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl und (C3-C6)Cycloalkyl, wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C4)Alkoxy, (Cι-C4)HaloaIkoxy, (d-C4)Alkylthio, und im Falle cyclischer Reste auch (d-C4)AIkyl und (d-C4)Haloalkyl substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel Q oder S(O)x , wobei x = 0, 1 oder 2 ist,, und A Wasserstoff oder (d-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-d)Alkoxy, (Cι-C4)Haloalkoxy, (Cι-C4)Alkylthio und im Falle cyclischer Reste auch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, vorzugsweise einen Acylrest aus der Gruppe, die aus den Resten (d-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl besteht, bedeuten, bedeutet.(R 4 ) m rn radicals R 4 , each of the radicals R 4 independently of one another from the group of the radicals halogen, such as F, Cl, Br and I, and SCN, CN and (Cι-d) alkyl, (C 2 - C 4 ) alkenyl, (C 2 -C 4 ) alkynyl and (C 3 -C 6 ) cycloalkyl, each of the latter 4 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, (dC 4 ) alkoxy, ( Cι-C 4 ) HaloaIkoxy, (dC 4 ) alkylthio, and in the case of cyclic radicals also (dC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, and radicals of the formula -Z * -A is selected, wherein Z * is a group of the formula Q or S (O) x , where x = 0, 1 or 2, and A is hydrogen or (dC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, ( C 3 -C 6 ) Cycloalkyl where each of the latter 4 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, (-C-d) alkoxy, (Cι-C 4 ) haloalkoxy, (Cι-C 4 ) alkylthio and in the case of cyclic radicals also (dC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, or an acyl radical, above provided that Z * in the case of A = acyl can only be O or S, preferably an acyl radical from the group consisting of the radicals (dC 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [ (-C-C 4 ) haloalkoxy] carbonyl, mean, means.
Insbesondere bevorzugt bedeutet dabei Gruppe A-Z*- eine Hydroxygruppe oder eine Acyloxygruppe, z. B. Acetyloxy oder Propionyloxy.Particularly preferably, group A-Z * means a hydroxyl group or an acyloxy group, e.g. B. acetyloxy or propionyloxy.
Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formel (I), worin m 0, 1 , 2, 3 oder 4, vorzugsweise 0, 1 oder 2, insbesondere 1 bedeutet.The use according to the invention of compounds of the formula (I) in which m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, in particular 1, is particularly preferred means.
Dabei sind von besonderem Interesse Verbindungen der Formeln (1-1) oder deren Salze,Of particular interest are compounds of the formulas (1-1) or their salts,
worin R1, R2, R3, R4 und m wie in Formel (I) definiert sind. Die Verbindungen (1-1) können als Z und E-Isomere an der Doppelbindung auftreten (= Verbindungen (1-1 a) und-(l-lb)), wobei diese in den meisten Fällen miteinander im Gleichgewicht stehen und das jeweilige E-Isomer bzw. das Isomer (1-1 a) in der Regel das stabilere Isomer darstellt:wherein R 1 , R 2 , R 3 , R 4 and m are as defined in formula (I). The compounds (1-1) can occur as Z and E isomers on the double bond (= compounds (1-1 a) and- (l-lb)), these being in most cases in equilibrium with one another and the respective E Isomer or the isomer (1-1 a) generally represents the more stable isomer:
(1-1 a) (1-1 b)(1-1 a) (1-1 b)
Von besonderem Interesse sind die Verbindungen der Formeln (I-2), (I-3), (I-4), (l-5) oder auch die weiter substituierten Verbindungen der Formeln (I-6), (I-7), (I-8), (I-9), (1-10) und (1-11): Of particular interest are the compounds of the formulas (I-2), (I-3), (I-4), (I-5) or the further substituted compounds of the formulas (I-6), (I-7) , (I-8), (I-9), (1-10) and (1-11):
(1-2) (1-3) (1-4)(1-2) (1-3) (1-4)
(1-5) (1-6) (1-7)(1-5) (1-6) (1-7)
(1-10) (1-11 ) wobei in den Formeln (I-2) bis (1-11 ) jeweils R1, R2, R3, R4 und m wie für Formel (I) definiert sind und wobei die R4 unabhängig voneinander definiert sind, d. h. gleiche oder verschiedene Reste bedeuten.(1-10) (1-11) where in the formulas (I-2) to (1-11) each R 1 , R 2 , R 3 , R 4 and m are as defined for formula (I) and the R 4 are defined independently of one another, ie the same or mean different residues.
Bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formeln (I-2) bis (1-10), vorzugsweise der Formeln (I-3), (I-4), (I-5) und auch (I-6) bis (1-11) oder deren Salzen, worin jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen und (CrC4)Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C )A!koxy, (d- C )Haloalkoxy, substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel Q oder S und A Wasserstoff oder (d-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (C3-C6)Cycloalkyl wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Ci-dJAlkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (d-C4)AIkylsulfinyl, (d- C4)Alkylsulfonyl, (d-C4)Alkanoyl, (C1-C4)Haloalkanoyl, [(d-dJAlkoxyjcarbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Cι-C )Haloalkyl substituiert ist, oder einen Acylrest, vorzugsweise einen Acylrest aus der Gruppe, die aus den Resten (d-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(d-C4)AIkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl besteht, bedeuten.Preferred is the use according to the invention of compounds of the formulas (I-2) to (1-10), preferably of the formulas (I-3), (I-4), (I-5) and also (I-6) to ( 1-11) or their salts, in which each of the radicals R 4 independently of one another from the group of the radicals halogen and (CrC 4 ) alkyl, which is unsubstituted or by one or more radicals from the group halogen, hydroxy, (dC) A! Koxy , (d- C) haloalkoxy, is substituted, and radicals of the formula -Z * -A is selected, where Z * is a group of the formula Q or S and A is hydrogen or (dC 4 ) alkyl, (C 2 -C 4 ) Alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl where each of the latter 4 radicals is unsubstituted or by one or more radicals from the group halogen, hydroxy, (Ci-dJalkoxy, (dC 4 ) haloalkoxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (dC 4 ) alkanoyl, (C 1 -C 4 ) haloalkanoyl, [(d-dJalkoxyjcarbonyl and in the case of cyclic radicals also (dC 4 ) Alkyl and (-C-C) haloalkyl is substituted, or an acyl radical , preferably an acyl radical from the group consisting of the radicals (dC 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl.
Besonders bevorzugt ist die erfindungsgemäße Verwendung von Verbindungen der Formeln (1-1) bis (1-11), vorzugsweise der Formeln (I-2), (I-3), (I-4) und (I-5) oder deren Salzen, worin jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, Methyl, Ethyl, n-Propyl, i-Propyl, Hydroxymethyl, Methoxymethyl, Dimethoxymethyl, Hydroxy, Methoxy, Ethoxy, Acetoxy, Propionyloxy, Trifluoracetoxy ausgewählt ist, vorzugsweise in Kombination mit den bevorzugten Resten und Bedeutungen für R1,The use according to the invention of compounds of the formulas (1-1) to (1-11), preferably of the formulas (I-2), (I-3), (I-4) and (I-5) or their compounds, is particularly preferred Salts in which each of the R 4 radicals independently of one another from the group consisting of halogen, methyl, ethyl, n-propyl, i-propyl, hydroxymethyl, methoxymethyl, dimethoxymethyl, hydroxy, methoxy, ethoxy, acetoxy, propionyloxy, trifluoroacetoxy is selected, preferably in combination with the preferred radicals and meanings for R 1 ,
R2 und R3.R 2 and R 3 .
Beispiele für erfindungsgemäß einzusetzende Verbindungen sind in den untenstehenden Tabellen aufgeführt.Examples of compounds to be used according to the invention are listed in the tables below.
Die Verbindungen der Formel (I) sind teilweise bekannt oder können analog bekannten Verfahren hergestellt werden. Ihre Anwendung als Safener in Pflanzen gemäß der erfindungsgemäßen Verwendung 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 in plants according to the use according to the invention has hitherto 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 analog bekannten Verfahren, wie sie zur Herstellung von Zimtsäuren und deren Derivaten beschrieben sind, hergestellt werden. Die Säurederivate wie Aldehyde und Ketone werden ebenfalls gemäß oder analog bekannten Verfahren erhalten (siehe Referenzwerke und Handbücher der preparativen Organischen Chemie, beispielsweise, Houben Weyl, Organic Synthesis, und dort zitierte Literatur).The compounds of the formula (I) can be prepared analogously to known processes as described for the preparation of cinnamic acids and their derivatives. The acid derivatives such as aldehydes and ketones are likewise obtained in accordance with or analogously to known processes (see reference works and manuals of preparative organic chemistry, for example, Houben Weyl, Organic Synthesis, and the literature cited therein).
Gegenstand der Erfindung ist auch das Verfahren zum Schützen von Kultur- oder Nutzpflanzen vor phytotoxischen Wirkungen von Agrochemikalien, wie Pestiziden oder Düngemitteln, oder vor Umweltfaktoren, welche Schäden an Pflanzen verursachen, dadurch gekennzeichnet, dass man Verbindungen der Formel (I) oder deren Salze als Safener anwendet, vorzugsweise eine effektive Menge der Verbindungen der Formel (I) oder deren Salzen auf die Pflanzen, Teile der Pflanzen oder deren 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 fertilizers, or from environmental factors which cause damage to plants, characterized in that compounds of the formula (I) or their salts are used as Safener applies, preferably an effective amount of the compounds of formula (I) or their salts applied to the plants, parts of the plants or their seeds or seeds thereof.
Die Safener sind geeignet, zusammen mit agrochemischen Wirkstoffen (Pestiziden oder Düngemitteln), vorzugsweise Pestiziden zur selektiven Bekämpfung von Schadorganismen, in einer Reihe von Pflanzenkulturen eingesetzt zu werden, beispielsweise in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Triticale, 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 monokotylen Gemüsekulturen, aber auch in dikotylen Kulturen wie beispielsweise Soja, Raps, Baumwolle, Wein, Gemüsepflanzen, Obstpflanzen und Zierpflanzen. Dabei sind auch gegenüber den Pestiziden partiell tolerante Mutantenkulturen oder partiell tolerante transgene Kulturen von Interesse, z. B. Maiskulturen, die gegenüber Glufosinate oder Glyphosate resistent ist, oderThe safeners are suitable, together with agrochemical active substances (pesticides or fertilizers), preferably pesticides for the selective control of Harmful organisms to be used in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, rye, triticale, rice, corn, millet), sugar beet, sugar cane, rapeseed, cotton and soy. Of particular interest is the application in monocotyledon crops such as cereals (wheat, barley, rye, triticale, sorghum), including corn and rice, and monocotyledon vegetable crops, but also in dicotyledon 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 that are resistant to glufosinate or glyphosate, or
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.Soy crops 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 Agrochemikalien/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, Insektizide oder Fungizide 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 simultaneously with the active ingredients or in any order with the active ingredients for agrochemicals / pesticides and are then able to reduce or completely eliminate harmful side effects of these active ingredients in crop plants without the effectiveness of these active ingredients against undesirable harmful organisms or significantly reduce them. Damage caused by the use of several pesticides, e.g. by several herbicides, insecticides or fungicides 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. z. B. 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 method - ie immediately before application to the surface to be treated If 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, e.g. 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 Pestiziden, z. B. Herbiziden, neben der Safenerwirkung auch Wirkungsverstärkungen, z. B. 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. 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.Often when using the compounds (I) according to the invention in combination with pesticides, for. B. herbicides, in addition to the safener effect and enhancements, z. B. observed in herbicidal activity against harmful plants. Furthermore, the growth of crops and crops has improved in many cases, and crop yields can be increased. 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 pesticides are herbicides, insecticides, fungicides, acaricides and nematicides, which, when used alone, cause phytotoxic damage to the Crops would result or where 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 application rate of safener can be varied within wide limits depending on the pesticide used and the type of crop to be protected 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 each hectares.
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 üblicherweise separat oder zusammen mit den Agrochemikalien, z. B. Pestiziden oder Düngemitteln, formuliert werden. Gegenstand sind daher auch die nutzpflanzen- oder kulturpflanzenschützenden Mittel.The safeners can usually be used separately or together with the agrochemicals, e.g. B. pesticides or fertilizers. The subject is therefore also the crop or crop protection agents.
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 Handelsnamen und common names wie sie in "Compendium 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-propenyIacetamide; CDEC, i.e. 2-chloroallyl diethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl; chlorbromuron; chlorbufam; chlorfenac; chlorfenprop, chlorflurenol-methyl; chloridazon; chlorimuron(-ethyl); chlomitrofen; 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); diciofop and its esters such as diclofop-methyl; diclosulam, diethatyl(-ethyl); difenoxuron; difenzoquat; diflufenican; diflufenzopyr; dimefuron; dimepiperate; dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethenamid(-P); dimethazone, dimethipin; dimexyflam, dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, i.e. 5-cyano- 1-(1 ,1-dimethylethyl)-N-methyl-1 H-pyrazole-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- fluoropropyl)-4,5-dihydro-5-oxo-1 H-tetrazol-1 -yl]-phenyl]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; flufenacetHerbicides whose phytotoxic side effects on crop plants can be reduced by means of compounds of the formula (I) can be used entirely different structure 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 trade names and common names as described in "Compendium of Pesticide Common Names "(can be queried via 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-propenyIacetamide; 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); diciofop and its esters such as diclofop-methyl; diclosulam, diethatyl (ethyl); difenoxuron; difenzoquat; diflufenican; diflufenzopyr; dimefuron; dimepiperate; dimethachlor; dimethametryn; dimethenamid (SAN-582H); dimethenamid (-P); dimethazone, dimethipin; dimexyflam, dimetrasulfuron, dinitramine; dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron; DNOC; eglinazine-ethyl; EL 77, ie 5-cyano-1- (1, 1-dimethylethyl) -N-methyl-1H-pyrazole-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-fluoropropyl) -4,5-dihydro-5-oxo-1 H-tetrazol-1-yl] phenyl] 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, flumetsuiam; 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; imazamethabenz(-methyl); imazamethapyr; imazamox; imazapic, imazapyr; imazaquin and salts such as the ammonium salts; imazethamethapyr; imazethapyr, imazosulfuron; indanofan; iodosulfuron-(methyl)-(sodium), ioxynil; isocarbamid; isopropalin; 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-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; 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)phenyl]-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]-1H- tetrazole; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-(FOE 5043), flufenpyr, flumetsuiam; 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; imazamethabenz (-methyl); imazamethapyr; imazamox; imazapic, imazapyr; imazaquin and salts such as the ammonium salts; imazethamethapyr; imazethapyr, imazosulfuron; indanofan; iodosulfuron- (methyl) - (sodium), ioxynil; isocarbamid; isopropalin; 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] -1H-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.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 mittelsHerbicides, the phytotoxic side effects of which on crops
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- benzpesäure-Derivate, Sulfonylhamstoffe, Sulfonylaminocarbonyltriazolinone, Triazolo-pyrimidin-sulfonamid-Derivate, Phosphinsäurederivate und deren Salze, Glyzinderivate, Triazolinone, Triazinone sowie S-(N-Aryl-N-alkylcarbamoylmethyl)- dithiophosphorsäureester. Pyridincarbonsäuren, Pyridine, Pyridincarboxamide, 1 ,3,5-Triazine, und weitere.Compounds of formula I which can be reduced 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-pyridinecarboxylic acid derivatives, pyrimidyloxybenzoic acid derivatives, sulfonylureas, sulfonylaminocarbonyltriazolinones, triazolo-pyrimidinesulfonamide derivatives, saline, triazolonezone derivatives, phosphinaziazine derivatives, phosphinaziazine derivatives, phosphinsidiazinone derivatives, phosphinaziazine derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinsidiazinone derivatives, phosphinaziazine derivatives, -N-alkylcarbamoylmethyl) dithiophosphoric acid ester. Pyridinecarboxylic acids, pyridines, pyridinecarboxamides, 1, 3,5-triazines, and others.
Bevorzugt sind dabei Phenoxyphenoxy- und Heteroaryloxyphenoxycarbonsäureester und -salze, Cyclohexandionoxime, Benzoylcyclohexandione, Benzoylisoxazole, Sulfonylhamstoffe, Sulfonylaminocarbonyltriazolinone, Imidazolinone sowie Mischungen der genannten Wirkstoffe untereinander und/oder mit Wirkstoffen, die zur Erweiterung des Wirkungsspektrums der Herbizide eingesetzt werden, z.B. Bentazon, Cyanazin, Atrazin, Bromoxynil, Dicamba und andere Blattherbizide. Geeignete Herbizide, die mit den erfindungsgemäßen Safenern kombiniert werden können, sind beispielsweise: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 the active ingredient, C, are used for the herbicide spectrumazonazione , Bromoxynil, dicamba and other leaf herbicides. Suitable herbicides which can be combined with the safeners according to the invention are, for example:
A) Herbizide vom Typ der Phenoxyphenoxy- undA) 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), 2-(4-(4-Brom-2-fluorphenoxy)phenoxy)propionsäuremethylester (US-A 4,808,750),Methyl 2- (4- (4-bromo-2-chlorophenoxy) phenoxy) propionate (DE-A 26 01 548), methyl 2- (4- (4-bromo-2-fluorophenoxy) phenoxy) propionate (US-A 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-Fluor-4-irifluormethylphenoxy.)phenoxy)propionsäuremethyIester (US-A-2- (4- (2-Fluoro-4-irifluoromethylphenoxy.) Phenoxy) propionic acid methyl ester (US-A-
4,808,750), 2-(4-(2,4-Dichlorbenzyl)phenoxy)propionsäuremethylester (DE-A 24 17 487),4,808,750), 2- (4- (2,4-dichlorobenzyl) phenoxy) propionic acid methyl ester (DE-A 24 17 487),
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-butyI)(R) -2- [4- (4-cyano-2-fluorophenoxy) phenoxy] butyl propionate (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-pyridyloxy)phenoxy)propionsäure- methylester (Haloxyfop-methyl bzw. Haloxyfop-P-methyl),(RS) - or (R) -2- (4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy) propionic acid methyl ester (haloxyfop-methyl or haloxyfop-P-methyl),
2-(4-(3-Chlor-5-trifluormethyI-2-pyridyloxy)phenoxy)propionsäureethylester2- (4- (3-chloro-5-trifluormethyI-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), (RS)- oder (R)-2-(4-(5-Trifluormethyl-2-pyridyIoxy)phenoxy)propionsäurebutylester(Clodinafop-propargyl), (RS) - or (R) -2- (4- (5-trifluoromethyl-2-pyridyIoxy) 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 A3) "Zweikernige" Heteroaryloxyphenoxy-alkancarbonsäure-Derivate, z.B.(r?) - 2- [4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenoxy] propionic acid A3) "dinuclear" heteroaryloxyphenoxy alkane carboxylic acid derivatives, for example
(RS)- oder (f?)-2-(4-(6-Chlor-2-chinoxalyIoxy)phenoxy)propionsäuremethylester und(RS) - or (f?) - 2- (4- (6-chloro-2-quinoxalyIoxy) phenoxy) propionic acid methyl ester and
-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.-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.
10, 61 (1985)),10, 61 (1985)),
(R)-2-(4-(6-Chlor-2-chinoxalyloxy)phenoxy)propionsäure-2-isopropylidenaminooxy- ethylester (Propaquizafop),(R) -2- (4- (6-chloro-2-quinoxalyloxy) phenoxy) propionic acid 2-isopropylidene aminooxy ethyl ester (propaquizafop),
(RS)- oder (f?)-2-(4-(6-ChlorbenzoxazoI-2-yl-oxy)phenoxy)propionsäureethylester (Fenoxaprop-ethyl bzw. Fenoxaprop-P-ethyl),(RS) - or (f?) - 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)propionsäureethyIester (DE-A-2640 730),2- (4- (6-chlorobenzthiazol-2-yloxy) phenoxy) propionic acid ethyl ester (DE-A-2640 730),
(RS)- oder (f?)-2-(4-(6-Chlorchinoxalyloxy)phenoxy)propionsäure-tetrahydro-2- furylmethylester (EP-A-0 323 727);(RS) - or (f?) - 2- (4- (6-chloroquinoxalyloxy) phenoxy) propionic acid tetrahydro-2-furylmethyl ester (EP-A-0 323 727);
B) Herbizide aus der Reihe der Sulfonylhamstoffe, wie Pyrimidin- oderB) herbicides from the series of sulfonylureas, such as pyrimidine or
Triazinylaminocarbonyl-[benzol-, pyridin-, pyrazol-, thiophen- und (alkylsulfonyl)- alkylamino-]-suIfamide. Bevorzugt als Substituenten am Pyrimidinring oder Triazinring sind Alkoxy, Alkyl, Haloalkoxy, Haloalkyl, Halogen oder Dimethylamino, wobei alle Substituenten unabhängig voneinander kombinierbar sind. Bevorzugte Substituenten im Benzol-, Pyridin-, Pyrazol-, Thiophen- oder (Alkylsulfonyl)- alkylamino-Teil sind Alkyl, Alkoxy, Halogen, Nitro, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkoxyaminocarbonyl, Halogenalkoxy, Halogenalkyl, Alkylcarbonyl, Alkoxyalkyl, (Alkansulfonyl)alkylamino. Solche geeignete Sulfonylhamstoffe sind beispielsweise B1 ) Phenyl- und Benzylsulfonylharnstoffe und verwandte Verbindungen, z.B. 1-(2-Chlorphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)harnstoff (Chlorsulfuron), 1-(2-Ethoxycarbonylphenylsulfonyl)-3-(4-chlor-6-methoxypyrimidin-2-yl)harnstoff (Chlorimuron-ethyl), 1 -(2-Methoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)hamstoff (Metsulfuron-methyl), 1-(2-Chlorethoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)ham-stoff (Triasulfuron),Triazinylaminocarbonyl- [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] suIfamide. Preferred substituents on the pyrimidine ring or triazine ring are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino, where all substituents can be combined independently of one another. Preferred substituents in the benzene, pyridine, pyrazole, thiophene or (alkylsulfonyl) alkylamino part are alkyl, alkoxy, halogen, nitro, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy, haloalkyl, alkylcarbonyl, alkoxyalkyl, ( alkanesulfonyl) alkylamino. Examples of suitable sulfonylureas are B1) phenyl- and benzylsulfonylureas and related compounds, for example 1- (2-chlorophenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) urea (chlorosulfuron ), 1- (2-ethoxycarbonylphenylsulfonyl) -3- (4-chloro-6-methoxypyrimidin-2-yl) urea (chlorimuron-ethyl), 1 - (2-methoxyphenylsulfonyl) -3- (4-methoxy-6-methyl -1, 3,5-triazin-2-yl) urea (metsulfuron-methyl), 1- (2-chloroethoxyphenylsulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl ) ham-material (Triasulfuron),
1-(2-Methoxycarbonylphenylsulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)hamstoff1- (2-Methoxycarbonylphenylsulfonyl) -3- (4,6-dimethylpyrimidin-2-yl) urea
(Sulfumeturon-methyl),(Sulfumeturon-methyl),
1-(2-MethoxycarbonylphenyIsulfonyl)-3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)-3- methylharnstoff (Tribenuron-methyl),1- (2-methoxycarbonylphenylisulfonyl) -3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) -3-methylurea (tribenuron-methyl),
1-(2-Methoxycarbonylbenzylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yI)hamstoff1- (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), 3-(4-Ethyl-6-methoxy-1 ,3,5-triazin-2-yl)-1-(2,3-dihydro-1 ,1-dioxo-2-methyIbenzo-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-
[b]thiophen-7-sulfonyl)harnstoff (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-benzoesäuremethyIester (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), 4-lod-2-[3-(4-methoxy-6-methyl-1 ,3,5-triazin-2-yl)ureidosulfonyl]- benzoesäuremethylester, Natriumsalz (lodosulfuron-methyl-Natrium)(CGA-277476, oxasulfuron), 4-iodo-2- [3- (4-methoxy-6-methyl-1, 3,5-triazin-2-yl) ureidosulfonyl] benzoic acid methyl ester, sodium salt (iodosulfuron-methyl-sodium )
2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyI]-4-methansulfonylamino-methyl- benzoesäuremethylester (Mesosulfuron-methyl, WO 95/10507),2- [3- (4,6-dimethoxypyrimidin-2-yl) ureidosulfonyI] -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]hamstoff1- (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)carbamoylsulfamoyl]benzoesäure- methylester (Ethametsulfuron-methyl); 1 -(4-Methoxy-6-methyl-1 ,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]- harnstoff (Prosulfuron);2 - [(4-Ethoxy-6-methylamino-1, 3,5-triazin-2-yl) carbamoylsulfamoyl] methyl benzoate (ethametsulfuron-methyl); 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)benzoesäuremethylester (Sulfometuron-methyl);2- (4,6-dimethylpyrimidin-2-ylcarbamoylsulfamoyl) benzoate (Sulfometuron methyl);
1-(4-Methoxy-6-trifluoromethyl-1 ,3,5-triazin-2-yI)-3-(2-trifluoromethylbenzolsulfonyl)- harnstoff (Tritosulfuron);1- (4-methoxy-6-trifluoromethyl-1, 3,5-triazin-2-yI) -3- (2-trifluoromethylbenzenesulfonyl) urea (tritosulfuron);
B2) Thienylsulfonylhamstoffe, z.B.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. 1-(4-EthoxycarbonyI-1-methylpyrazol-5-yI-sulfonyl)-3-(4,6-dimethoxypyrimidin-2- yl)hamstoff (Pyrazosulfuron-ethyl);B3) pyrazolylsulfonylureas, e.g. 1- (4-EthoxycarbonyI-1-methylpyrazol-5-yI-sulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (pyrazosulfuron-ethyl);
3-ChIor-5-(4,6-dimethoxypyrimidin-2-ylcarbamoyIsulfamoyl)-1-methyl-pyrazoI-4- carbonsäuremethylester (Halosulfuron-methyl);3-chloro-5- (4,6-dimethoxypyrimidin-2-ylcarbamoyisulfamoyl) -1-methyl-pyrazoI-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-2H-tetrazol-5-yl)pyrazol-5- ylsulfonyljhamstoff (DPX-A8947, Azimsulfuron);1- (4,6-Dimethoxypyrimidin-2-yl) -3- [1-methyl-4- (2-methyl-2H-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-methylsulfonylaminosulfonyl)- 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-methylsulfonylaminosulfonyl) urea (amidosulfuron) and its structural analogues (EP-A 0 131 258 and Z. Pfl. Krankh. Pfl. Schutz , Special Issue XII, 489-497 (1990));
B5) Pyridylsulfonylhamstoffe, z.B.B5) pyridylsulfonylureas, e.g.
1-(3-N,N-Dimethylaminocarbonylpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2- yl)harnstoff (Nicosulfuron),1- (3-N, N-dimethylaminocarbonylpyridin-2-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea (nicosulfuron),
1-(3-EthylsulfonyIpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)harnstoff1- (3-EthylsulfonyIpyridin-2-ylsulfonyl) -3- (4,6-dimethoxypyrimidin-2-yl) urea
(Rimsulfuron), 2-[3-(4,6-Dimethoxypyrimidin-2-yl)ureidosulfonyl]-6-trifluormethyl-3-pyridin- carbonsäuremethylester, Natriumsalz (DPX-KE 459, Flupyrsulfuron-methyl-natrium),(Rimsulfuron), 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-Dimethoxypyrimidinyl-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); 1-(4,6-Dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)harnstoff (Flazasulfuron);3- (4,6-Dimethoxypyrimidinyl-2-yl) -1- (3-N-methylsulfonyl-N-methyl-aminopyridin-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) urea (flazasulfuron);
1-(4,6-Dimethoxypyrimidin-2-yl)-3-[3-(2,2,2-trifluoroethoxy)-2- pyridylsulfonyl]harnstoff-Natriumsalz,(Trifloxysulfuron-natrium);1- (4,6-Dimethoxypyrimidin-2-yl) -3- [3- (2,2,2-trifluoroethoxy) -2-pyridylsulfonyl] urea sodium salt, (trifloxysulfuron sodium);
B6) Alkoxyphenoxysulfonylharnstoffe,B6) alkoxyphenoxysulfonylureas,
3-(4,6-Dimethoxypyrimidin-2-yl)-1 -(2-ethoxyphenoxy)-sulfonyIhamstoff oder dessen3- (4,6-Dimethoxypyrimidin-2-yl) -1 - (2-ethoxyphenoxy) sulfonylurea or its
Salze (Ethoxysulfuron);Salts (ethoxysulfuron);
B7) Imidazolylsulfonylharnstoffe, z.B.B7) imidazolylsulfonylureas, e.g.
1-(4,6-Dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonyIimidazo[1 ,2-a]pyridin-3- yI)sulfonylharstoff (MON 375Q0, Sulfosulfuron);1- (4,6-Dimethoxypyrimidin-2-yl) -3- (2-ethylsulfonyimidazo [1, 2-a] pyridin-3-yI) sulfonyl urea (MON 375Q0, sulfosulfuron);
1-(2-ChIoroimidazo[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,Acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, metazachlor,
Metolachlor, S-Metolachlor, Pethoxamid, Pretilachlor, Propachlor, Propisochlor undMetolachlor, S-metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor and
Thenylchlor;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. Alloxydim, Butroxydim, Clethodim, Cloproxydim, Cycloxydim, Protoxydim, Sethoxydim, Tepraloxydim und Tralkoxydim;E) Cyclohexanedione oximes, e.g. Alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, protoxydim, sethoxydim, tepraloxydim and tralkoxydim;
F) Imidazolinone, z.B. Imazamethabenz-methyl, Imazapic, Imazamox, Imazapyr, Imazaquin und Imazethapyr;F) imidazolinones, e.g. Imazamethabenz-methyl, imazapic, imazamox, imazapyr, imazaquin and imazethapyr;
G) Triazolopyrimidinsulfonamid-Derivate, z.B. Chloransulam-methyl, Diclosulam, Florasulam, Flumetsulam, Metosulam und Penoxulam;G) triazolopyrimidine sulfonamide derivatives, e.g. Chloransulam-methyl, diclosulam, florasulam, flumetsulam, 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-Nitrobenzoyl)-4,4-dimethyl-cyclohexan-1 ,3-dion (EP-A 0 274 634), 2-(2-Nitro-3-methylsulfonylbenzoyl)-4,4-dimethylcyclohexan-1 ,3-dion (WO 91/13548); 2-[4-(Methylsulfonyl)-2-nitrobenzoyI]-1 ,3-cycIohexanedion (Mesotrione)2- (2-chloro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione (SC-0051, sulcotrione), 2- (2-nitrobenzoyl) -4,4-dimethylcyclohexane-1,3-dione (EP -A 0 274 634), 2- (2-nitro-3-methylsulfonylbenzoyl) -4,4-dimethylcyclohexane-1,3-dione (WO 91/13548); 2- [4- (methylsulfonyl) -2-nitrobenzoyI] -1, 3-cycIohexanedione (mesotrione)
I) Benzoylisoxazole, z. B. 5-Cyclopropyl-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyI]-isoxazol (Isoxaflutole)I) benzoylisoxazoles, e.g. B. 5-Cyclopropyl- [2- (methylsulfonyl) -4- (trifluoromethyl) benzoyI] isoxazole (isoxaflutole)
J) Benzoylpyrazole, z. B.J) Benzoylpyrazole, e.g. B.
2-[4-(2,4-Dichlor-/77-toluoyl)-1 ,3-dimethylpyrazol-5-yloxy]-4'-methylacetophenon (Benzofenap); 4-(2,4-Dichlorbenzoyl)-1 ,3-dimethyIpyrazol-5-yl toIuene-4-sulfonate (Pyrazolynate); 2-[4-(2,4-Dichlorbenzoyl)-1 ,3-dimethylpyrazol-5-yloxy]acetophenone (Pyrazoxyfen);2- [4- (2,4-dichloro- / 77-toluoyl) -1, 3-dimethylpyrazol-5-yloxy] -4'-methylacetophenone (benzofenap); 4- (2,4-dichlorobenzoyl) -1, 3-dimethyIpyrazol-5-yl toIuene-4-sulfonate (pyrazolynate); 2- [4- (2,4-dichlorobenzoyl) -1, 3-dimethylpyrazol-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 /-/-1 ,2,4-triazol-1 -yl)- carboxamidosulfonylbenzoesäure-methylester-Natriumsalz (Propoxycarbazone-Na); L) Triazolinone, z. B.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 / - / - 1, 2,4-triazol-1-yl) carboxamidosulfonylbenzoic acid methyl ester sodium salt (propoxycarbazone-Na); L) triazolinones, e.g. B.
4-Amino-/V-fe/ -butyl-4,5-dihydro-3-isopropyl-5-oxo-1 ,2,4-1 H-triazole-1 -carboxamid4-Amino / V-fe / butyl-4,5-dihydro-3-isopropyl-5-oxo-1, 2,4-1 H-triazole-1-carboxamide
(Amicarbazone); 2-(2,4-Dichlor-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1 ,2,4-triazolo[4,3-a]pyridin-(Amicarbazone); 2- (2,4-dichloro-5-prop-2-ynyloxyphenyl) -5,6,7,8-tetrahydro-1, 2,4-triazolo [4,3-a] pyridine-
3(2H)-one (Azafenidin);3 (2H) -one (azafenidin);
(f?S)-2-Chlor-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1 ,2,4- triazol-1-yl)-4-fluorophenyl]propionsäureethylester (Carfentrazone-ethyl);(f? S) -2-chloro-3- [2-chloro-5- (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1, 2,4-triazol-1- yl) -4-fluorophenyl] propionic acid ethyl ester (Carfentrazone-ethyl);
2',4'-Dichlor-5'-(4-difluormethyI-4,5-dihydro-3-methyl-5-oxo-1 H-1 ,2,4-triazol-1 -yl)- methanesulfonanilid (Sulfentrazone);2 ', 4'-dichloro-5' - (4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1, 2,4-triazol-1-yl) methanesulfonanilide (sulfentrazone) ;
M) Phosphinsäuren und Derivate, z. B.M) phosphinic acids and derivatives, e.g. B.
4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-aIanyl-L-alanin-(Bilanafos);4- [hydroxy (methyl) phosphinoyl] -L-homoalanyl-L-aIanyl-L-alanine (bilanafos);
DL-Homoalanin-4-yl(methyl)phosphinsäure-ammoniumsalz (Glufosinate-ammonium)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);
/V-(Phosphonomethyl)glyzin-trimesiumsalz (Sulfosate)/ V- (phosphonomethyl) glycine trimesium salt (sulfosate)
O) Pyrimidinyloxy-pyridincarbonsäure-Derivate bzw.O) pyrimidinyloxy-pyridinecarboxylic acid derivatives or
Pyrimidinyloxybenzoesäure-Derivate, z.B.Pyrimidinyloxybenzoic acid derivatives, e.g.
3-(4,6-Dimethoxypyrimidin-2-yl)-oxy-pyridin-2-carbonsäurebenzyl-ester (EP-A3- (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-A0 249 707), 3- (4,6-Dimethoxypyrimidin-2-yl) -oxypyridine-2-carboxylic acid methyl ester (EP-A
0 249 707),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- ChIorphenyl)-N-isopropyl-carbamoylmethyl]-O,O-dimethyl-dithiophosphat (Anilophos);P) S- (N-aryl-N-alkyl-carbamoylmethyl) dithiophosphonic acid esters, such as S- [N- (4- Chlorophenyl) -N-isopropyl-carbamoylmethyl] -O, O-dimethyl-dithiophosphate (Anilophos);
Q) Triazinone, z. B. 3-Cyclohexyl-6-dimethylamino-1 -methyl-1 ,3,5-triazine-2,4-(1 H,3H)-d\on (Hexazinone);Q) triazinones, e.g. B. 3-Cyclohexyl-6-dimethylamino-1-methyl-1, 3,5-triazine-2,4- (1H, 3H) -d \ on (Hexazinone);
4-Amino-4,5-dihydro-3-methyl-6-phenyl-1 ,2,4-triazin-5-on (Metamitron); 4-Amino-6-fe/f-butyl-4,5-dihydro-3-methylthio-1 ,2,4-triazin-5-on (Metribuzin).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-one (metribuzin).
R) Pyridincarbonsäuren, z. B.R) pyridinecarboxylic acids, e.g. B.
Clopyralid, Fluroxypyr, Picloram und Triciopyr;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. Ametryn, Atrazine, Cyanazine, Dimethametrin, Prometon, Prometryn, Propazine, Simazine, Symetryn, Terbumeton, Terbuthylazine, Terbutryn und Trietazine;U) 1, 3,5-triazines, e.g. B. Ametryn, Atrazine, Cyanazine, Dimethametrin, Prometon, Prometryn, Propazine, 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, orthe 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.
Fungizide Wirkstoffe, welche in Kombination mit den erfindungsgemäßen nutzpflanzenschützenden Verbindungen (I) verwendet werden können sind vorzugsweise handelsübliche Wirkstoffe, beispielsweise (die Verbindungen sind analog den Herbiziden in der Regel in Form ihrer "Common Names" in englischerFungicidal active ingredients which can be used in combination with the crop protection compounds (I) according to the invention preferably commercially available active ingredients, for example (analogously to the herbicides, the compounds are generally in the form of their "common names" in English
Schreibweise bezeichnet):Spelled):
2-Phenylphenol; 8-Hydroxychinolinsulfat; acibenzolar-S-methyl; actinovate; aldimorph; amidoflumet; amprqpylfos; ampropylfos-potassium; andoprim;.anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl; benthiavalicarb- isopropyl; benzamacril; benzamacril-isobutyl; binapacryl; biphenyl; bitertanol; blasticidin-S; boscalid; bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvone; chinomethionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; cis-1 -(4-chlorophenyl)-2-(1 H-1 ,2,4-triazole-1 -yl)-cycloheptanol; clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine; dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; Edifenphos;2-phenylphenol; 8-hydroxyquinoline sulfate; acibenzolar-S-methyl; actinovate; aldimorph; amidoflumet; amprqpylfos; ampropylfos-potassium; andoprim; .anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl; benthiavalicarb isopropyl; benzamacril; benzamacril-isobutyl; binapacryl; biphenyl; bitertanol; blasticidin-S; boscalid; bromuconazole; bupirimate; buthiobate; butylamine; calcium polysulfide; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; chlobenthiazone; chlorfenazole; chloroneb; chlorothalonil; chlozolinate; cis-1 - (4-chlorophenyl) -2- (1 H-1, 2,4-triazole-1-yl) cycloheptanol; clozylacon; cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap; diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon; edifenphos;
Epoxiconazole; Ethaboxam; Ethirimol; Etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-AI; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazol; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tris(albesilate); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam; methyl 1-(2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl)-1 H-imidazoIe-5-carboxyIate; methyl 2-[[[cyclopropyl[(4-methoxyphenyl)imino]methyl]thio]methyI]-.alpha.- (methoxymethylene)- benzeneacetate; methyl 2-[2-[3-(4-chloro-phenyl)-1-methyl- aIlylideneaminooxymethyl]-phenyl]-3-methoxy-acrylate; metiram; metominostrobin; metrafenone; metsulfovax; mildiomycin; monopotassium carbonate; myclobutanil; myclozolin; N-(3-Ethyl-3,5,5-trimethyl-cyclohexyl)-3-formylamino-2-hydroxy- benzamide; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide; N-butyl-8-(1 ,1- dimethylethyl)-1-oxaspiro[4.5]decan-3-amine; natamycin; nitrothal-isopropyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin; oxyfenthiin; paclobutrazol; pefurazoate; penconazole; pencycuron; penthiopyrad; phosdiphen; phthalide; picobenzamid; picoxystrobin; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymidone; propamocarb; propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon; pyroxyfur; pyrrolnitrine; quinconazole; quinoxyfen; quintozene; silthiofam; simeconazole; sodium tetrathiocarbonate; spiroxamine; sulfur; tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; tiadinil; tioxymid; tolclofos-methyl; tolylfluanid; triadimefon; triadimenor; triazbutil; triazoxide; tricyclämide; tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole; uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2- propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl- 2-[(methylsulfonyl)amino]- butanamide; 1 -(1 -naphthalenyl)-1 H-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl)-pyridine; 2,4-Dihydro-5-methoxy-2-methyl-4-[[[[1-[3-(trifluoromethyl)- phenyl]-ethylidene]-amino]-oxy]-methyl]-phenyl]-3H-1 ,2,3-triazol-3-on; 2-Amino-4- methyl-N-phenyI-5-thiazolecarboxamid; 2-Chloro-N-(2,3-dihydro-1 ,1 ,3-trimethyl-1 H- inden-4-yl)-3-pyridincarboxamid; 3,4,5-Trichlor-2,6-pyridindicarbonitril; 3-[(3-Bromo- 6-fluor-2-methyl-1 H-indol-1-yl)sulfonyl]-N,N-dimethyl-1 H-1 ,2,4-triazol-1-sulfonamid; Kupfersalze und Kupferzubereitungen wie Bordeaux mixture; Kupferhydroxid; Kupfer-naphthenat; Kupfer-oxychlorid; Kupfersulfat; cufraneb; Kupfer-(l)-oxid; Mancopper; oxine-copper.epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram; fenhexamid; fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; fosetyl-AI; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; furcarbanil; furmecyclox; guazatine; hexachlorobenzene; hexaconazole; hymexazol; imazalil; imibenconazole; iminoctadine triacetate; iminoctadine tris (albesilate); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin; kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam; methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1 H -imidazole-5-carboxylates; methyl 2 - [[[cyclopropyl [(4-methoxyphenyl) imino] methyl] thio] methyl] -. alpha.- (methoxymethylene) - benzene acetates; methyl 2- [2- [3- (4-chlorophenyl) -1-methyl-allylideneaminooxymethyl] phenyl] -3-methoxy-acrylates; metiram; metominostrobin; metrafenone; metsulfovax; mildiomycin; monopotassium carbonate; myclobutanil; myclozoline; N- (3-ethyl-3,5,5-trimethyl-cyclohexyl) -3-formylamino-2-hydroxybenzamide; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine; natamycin; nitrothal-isopropyl; noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole; oxycarboxin; oxyfenthiin; paclobutrazol; pefurazoate; penconazole; pencycuron; penthiopyrad; phosdiphen; phthalide; picobenzamid; picoxystrobin; piperalin; polyoxins; polyoxorim; probenazole; prochloraz; procymidone; propamocarb; propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; pyroxyfur; pyrrolnitrine; quinconazole; quinoxyfen; quintozene; silthiofam; simeconazole; sodium tetrathiocarbonate; spiroxamine; sulfur; tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole; thicyofen; thifluzamide; thiophanate-methyl; thiram; tiadinil; tioxymid; tolclofos-methyl; tolylfluanid; triadimefon; triadimenor; triazbutil; triazoxide; tricyclämide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole; Uniconazole; validamycin A; vinclozolin; zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] butanamides ; 1 - (1-naphthalenyl) -1 H-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine; 2,4-Dihydro-5-methoxy-2-methyl-4 - [[[[1- [3- (trifluoromethyl) phenyl] ethylidene] amino] oxy] methyl] phenyl] -3H-1 , 2,3-triazol-3-one; 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide; 2-chloro-N- (2,3-dihydro-1,3,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; 3 - [(3-bromo-6-fluoro-2-methyl-1H-indol-1-yl) sulfonyl] -N, N-dimethyl-1H-1, 2,4-triazole-1-sulfonamide; Copper salts and copper preparations such as Bordeaux mixture; copper; Copper naphthenate; Copper oxychloride; Copper sulfate; cufraneb; Copper (I) oxide; mancopper; oxine-copper.
Insektizide und akarizide Wirkstoffe sind beispielsweise (Bezeichnung erfolgt analog den Herbiziden und Fungiziden möglichst als "Common Names" in englischer Schreibweise): alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilan, Ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, acephate, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphon, dialifos, diazinon, dichlofenthion, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/-ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vamidothion, acrinathrin, allethrin (d-cis-trans, d-trans), beta- cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin, deltamethrin, Empenthrin (1R-isomer), Esfenvalerate, Etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, Lambda-cyhalothrin, metofluthrin, permethrin (eis-, trans-), phenothrin (1 R-trans isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, Tau- fluvalinate, tefluthrin, terallethrin, tetramethrin (-1 R- isomer), tralomethrin, transfluthrin, ZXI 8901 , pyrethrins (pyrethrum), DDT, indoxaearb, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, bensultap, cartap, camphechlor, chlordane, Endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor spinosad, acetoprole, Ethiprole, fipronil, vaniliprole, avermectin, Emamectin, Emamectin-benzoate, ivermectin, milbemycin, diofenolan, Epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron, buprofezin, cyromazine, diafenthiuron, azocyclotin, cyhexatin, fenbutatin-oxide, chlorfenapyr, binapacyrl, dinobuton, dinocap, DNOC, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, hydramethylnon, dicofol, rotenone, acequinocyl, fluacrypyrim, Bacillus thuringiensis strains, spirodiclofen, spiromesifen, [3-(2,5-Dimethylphenyl)-8-methoxy- 2-oxo-l -azaspiro[4.5]dec-3-en-4-yl]-[ethyl]-carbonate (alias: carbonic acid, 3-(2,5- dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]deG-3-en-4-yl ethyl. ester, CAS- Reg.-No.: 382608-10-8) and carbonic acid, cis-3-(2,5-dimethylphenyl)-8-methoxy-2- oxo-1 -azaspiro[4.5]dec-3-en-4-yl ethyl ester (CAS-Reg.-No.: 203313-25-1), flonicamid, amitraz, propargite, N2-[1 ,1-Dimethyl-2-(methylsuIfonyl)ethyl]-3-iodo-N1- [2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]-1 ,2- benzenedicarboxamid (CAS-Reg.-No.: 272451-65-7), thiocyclam hydrogen oxalate, thiosultap-sodium, azadirachtin, Bacillus spec, Beauveria spec, codlemone, Metarrhizium spec, Paecilomyces spec, thuringiensin, Verticillium spec, aluminium phosphide, methyl bromide, sulfuryl fluoride, cryolite, flonicamid, pymetrozine, clofentezine, Etoxazole, hexythiazox, amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, chinomethionat, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyridalyl, sulfluramid, tetradifon, tetrasul, triarathene, verbutin.Insecticides and acaricidal active ingredients are, for example (name analogous to the herbicides and fungicides, if possible as "common names" in English spelling): alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxim, butoxycarboxofuran, carb . carbosulfan, cloethocarb, dimetilan, Ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanoxl, methacylphyx, trimethacarbyx, trimethacarbyx, trimethacarbyx, trimethacarbyx, trimethacarby X, trimethacarbyx, trimethacarbyx, trimethacarbyx, trimethacarbyx, trimethacarbyx, trimethacarbyx, trimethacarby X, trimethacarbyx, trimethacarbyx, trim azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl / -ethyl), coumaphos, cyanofenphos, cyanophos, chlorofos, cyanophos, cyanophos S-methyl, demetone-S-methylsulphone, dialifos, diazinon, dichlofenthion, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxabenzofos, disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, famphur, fenamiphos fionofionophion, fenitrothion, fenitrothion, phenitrion fonofos, formothion, fosmethilan, fosthiazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathio n, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl / -ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidon, phosphocarb, phoxim, pirimiphos (-methyl / -ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, cticlorfon, dhrinothin, dhrinothin, acrid, transhrinothin, acrid, transinion, dhrinothin, dhrinothin, dhrinothin, dhrinothin, transinionin , beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, cyclothrhrin, cyclothrin, beta, theta, zeta), cyphenothrin, deltamethrin, empenthrin (1R-isomer), Esfenvalerate, Etofenprox, fenfluthrin, fenpropathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flvalfenate, flumfenate, ma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (ice, trans-), phenothrin (1 R-trans isomer), prallethrin, profluthrin, protrifenbute, pyresmethrin, resmethrin, RU, 15525, silafluin , tefluthrin, terallethrin, tetramethrin (-1 R-isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrins (pyrethrum), DDT, indoxaearb, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, ninepyram, ninopyrine, naphyne, pyridine cartap, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor spinosad, acetoprole, ethiprole, fipronil, vaniliprole, avermectin, emamectin, emamectin-benzoate, ivermectin, milbemycin, diofenolan, epofenonane, fenoxycarb, hydroprene, chromripenifen, methoprene, methoprene, methoprene, methoprene, methoprene, methoprene , halofenozide, methoxyfenozide, tebufenozide, bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, cyphylurone, trifluridone, trifluridone, trifluridone , dinobuton, dinocap, DNOC, fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tuchtenpyrad, hydramethylnon, dicofol, roteone, acequinocyl, fluacrypyrim, Bacillus thuringiensis strains, spirodiclofen, spiromesifen, [3- (2,5-dimethylphenyl, methoxy-2-oxo-l-azaspiro [4.5] dec-3-en-4-yl] - [ethyl] carbonate (alias: carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2- oxo-1-azaspiro [4.5] deG-3-en-4-yl ethyl. ester, CAS Reg.No .: 382608-10-8) and carbonic acid, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3- en-4-yl ethyl ester (CAS Reg.No .: 203313-25-1), flonicamid, amitraz, propargite, N2- [1, 1-dimethyl-2- (methylsulfonyl) ethyl] -3-iodo- N1- [2-methyl-4- [1,2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl] -1, 2-benzenedicarboxamide (CAS Reg.No .: 272451-65-7) , thiocyclam hydrogen oxalate, thiosultap-sodium, azadirachtin, Bacillus spec, Beauveria spec, codlemone, Metarrhician spec, Paecilomyces spec, thuringiensin, Verticillium spec, aluminum phosphide, methyl bromide, sulfuryl fluoride, cryolite, flonicamid, pymetrozine, clythoxazez, clythoxazone , amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, pimplononeponepone, pionenzone, pylenononepure, pylenononepure l butoxide, potassium oleate, pyridalyl, sulfluramid, tetradifon, tetrasul, triarathene, verbutin.
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®), Phorate (Thimet®), Chlorpyriphos (Reldan®), Carbamate, wie Carbofuran (Furadan®), Pyrethroid-Insektizide, wie Tefluthrin (Force®), Deltamethrin (Decis®) und Tralomethrin (Scout®) sowie andere insektizide Mittel mit andersartigem Wirkmechanismus.Organophosphates e.g. Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate (Thimet ® ), Chlorpyriphos (Reldan ® ), Carbamates such as Carbofuran (Furadan ® ), Pyrethroid insecticides such as tefluthrin (Force ® ), deltamethrin (Decis ® ) and tralomethrin (Scout ® ) as well as other insecticidal agents with a different mode of action.
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 suitable types of formulation are:
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, wieDusts which are obtained by grinding the active ingredients with finely divided solid inorganic or organic substances, e.g. Talc, natural clays, like
Kaolin, Bentonit und Pyrophyllit, Diatomeenerde oder Mehlen erhalten werden.Kaolin, bentonite and pyrophyllite, diatomaceous earth or flours can be obtained.
Auf Wasser oder Öl basierende Suspensionskonzentrate, die beispielsweise durch Naßvermahlung mittels Perlmühlen hergestellt werden können;Suspension concentrates based on water or oil, which can be prepared, for example, by wet grinding using bead mills;
Wasserlösliche Pulver;Water soluble powder;
Wasserlösliche Konzentrate;Water soluble concentrates;
Granulate, wie wasserlösliche Granulate, wasserdispergierbare Granulate sowieGranules, such as water-soluble granules, water-dispersible granules and
Granulate für die Streu- und Bodenapplikation; Spritzpulver, die neben Wirkstoff noch Verdünnungs- oder Inertstoffe und Tenside enthalten;Granules for spreading and soil application; Wettable powders which, in addition to the active substance, also contain diluents or inert substances and surfactants;
Kapselsuspensionen und Mikrokapseln; Ultra-Low-Volume-Formulierungen.Capsule suspensions and microcapsules; 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.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, N.Y. 1973; Winnaker-Küchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th edition 1986; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, N.Y. 1973, pages 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 Athylenoxidaddukte", 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 necessary formulation auxiliaries 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 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, "Interface-active ethylene oxide adducts", Wiss. Publishing company, 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, "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. In emulsifiable concentrates this is Active substance concentration, ie the concentration of safener and / or pesticide, generally 1 to 90, in particular 5 to 80% by weight. 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 the commercial form are optionally diluted in the customary manner, e.g. for 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. With the external conditions such as temperature, humidity, the type of herbicide used u. a. the required application rate of the safener varies.
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
In der nachfolgenden Tabelle sind Beispiele für erfindungsgemäße Verbindungen (I) zusammengestellt; in der Tabelle 1 bedeuten:Examples of compounds (I) according to the invention are compiled in the table below; in Table 1 mean:
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 = Ethyl Me Methyl n-Pr n-Propyl i-Pr Isopropyl c-Pr Cyclopropyl i-Pen IsopentylEt = ethyl Me methyl n-Pr n-propyl i-Pr isopropyl c-Pr cyclopropyl i-pen isopentyl
R Substituent in 5 oder 6 Position am PhenylringR substituent in 5 or 6 position on the phenyl ring
R 5-Me bedeutet Methyl in 5-Position am Phenylring (siehe Nummerierung der Ringatome in der Formel (la))R 5-Me means methyl in the 5-position on the phenyl ring (see numbering of the ring atoms in the formula (Ia))
R H = nur Wasserstoff als Substituenten in Position 5 und 6 am PhenylR H = only hydrogen as substituents in positions 5 and 6 on the phenyl
Tabelle 1 : Verbindungen der Formel (I)Table 1: Compounds of formula (I)
B. Formulierungsbeispiele B. Examples of formulation
a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) oder einer Kombination von Verbindung (I) mit einem Pestizid und 9CLGew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.a) A dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) or a combination of compound (I) with a pesticide and 9CL parts by weight of talc as an inert substance and comminuting them in a hammer mill.
b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) oder einer Kombination von Verbindung (I) mit einem Pestizid, 64 Gewichtsteile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.b) A water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight . Part of oleoylmethyl tauric acid sodium mixed as a wetting and dispersing agent and ground in a pin mill.
c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gewichtsteile einer Verbindung der Formel (I) oder einer Kombination von Verbindung (I) mit einem Pestizid mit 6 Gew.-Teilen Alkylphenolpolyglykolether (©Triton X 207), 3 Gew.-Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Mineralöl (Siedebereich z.B. ca. 255 bis über 277°C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.c) A dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) or a combination of compound (I) with a pesticide with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3 parts by weight. Parts of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to above 277 ° C.) and ground in a attritor to a fineness of less than 5 microns.
d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer Verbindung der Formel (I) oder einer Kombination von Verbindung (I) mit einem Pestizid, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator.d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier ,
e) Ein in Wasser dispergierbares Granulat wird erhalten indem man 75 Gewichtsteile einer Verbindung der Formel (I) oder einer Kombination von Verbindung (I) mit einem Pestizid, 10 " ligninsulfonsaures Calcium, 5 " Natriumlaurylsulfat, 3 " Polyvinylalkohol und 7 " Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert.e) Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 10 "calcium lignosulfonic acid, 5" sodium lauryl sulfate, Mix 3 "polyvinyl alcohol and 7" kaolin, grind on a pin mill and granulate the powder in a fluidized bed by spraying water as granulating liquid.
f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) oder einer Kombination von Verbindung (I) mit einem Pestizid, 5 " 2,2'-dinaphthylmethan-6,6'-disuIfonsaures Natrium 2 " oleoylmethyltaurinsaures Natrium, 1 Gewichtsteil Polyvinylalkohol, 17 Gewichtsteile Calciumcarbonat und 50 " Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. f) Water-dispersible granules are also obtained by adding 25 parts by weight of a compound of formula (I) or a combination of compound (I) with a pesticide, 5 "2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium Homogenized 2 "oleoylmethyl tauric acid sodium, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50" water on a colloid mill and then comminuted it, then ground it on a bead mill and sprayed the resulting suspension in a spray tower using a single-component nozzle and dried it.
C) Biologische BeispieleC) Biological examples
C1 ) Herbizid und Safener im Tankmix als SpritzapplikationC1) Herbicide and safener in the tank mix as spray application
C1.1) Herbizid und Safener Vorauflaufanwendung im TankmischungsverfahrenC1.1) Herbicide and safener pre-emergence 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 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).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 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 spraying 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 and the herbicide isoxaflutole as an aqueous suspension concentrate (see Table 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). 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 1.1.1 : Vorauflaufanwendung: Herbizid und Safener im Tankmix-VerfahrenTable 1.1.1: Pre-emergence application: herbicide and safener in the tank mix process
Abkürzungen: Herbizid H1 = Isoxaflutole Verb. 17 2-Hydroxyzimtsäure (vgl Tab. 1 ) Verb. 155 = 2,4-Dichlorzimtsäure (vgl. Tab. 1 ) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' SETVI Setaria viridis CHEAL Chenopodium albumAbbreviations: herbicide H1 = isoxaflutole Verb. 17 2-hydroxycinnamic acid (see Tab. 1) Verb. 155 = 2,4-dichlorocinnamic acid (see Tab. 1) ZEAMA Zea mays (maize), cultivar 'Lorenzo' SETVI Setaria viridis CHEAL Chenopodium album
C1.2) Nachauflaufanwendung von Herbizid und Safener im Tankmix-verfahrenC1.2) 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 approximately 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 the uncovered part of the Applied floor 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 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 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. 17 2-Hydroxyzimtsäure (vgl Tab. 1) Verb. 155 = 2,4-Dichlorzimtsäure (vgl. Tab. 1) Verb. 154 = 4-Methoxyzimtsäure Verb. 146 = 2-Fluorzimtsäure Verb. 191 = 3-HydroxyzimtsäureethylesterAbbreviations: Herbicide H2 = Foramsulfuron Verb. 17 2-hydroxycinnamic acid (see Tab. 1) Verb. 155 = 2,4-dichlorocinnamic acid (see Tab. 1) Verb. 154 = 4-methoxycinnamic acid Verb. 146 = 2-Fluorocinnamic acid Verb. 191 = 3-hydroxycinnamic acid ethyl ester
ZEAMA = Zea mays (Mais), Sorte 'Lorenzo'ZEAMA = Zea mays (maize), variety 'Lorenzo'
SETVI = Setaria viridisSETVI = Setaria viridis
AMARE = Amaranthus retroflexusAMARE = Amaranthus retroflexus
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, wässrige Lösungen) 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 grünen Pflanzenteile und auf den unbedeckten Teil der Bodenoberfläche appliziert. Im nachfolgend dargestellten Versuch wurden die Safener als 20 prozentiges wasserdispergierbares Pulver, das Herbizid Glufosinate-Ammonium als handelsübliche 20 prozentige wässrige tensidhaltige Lösung verwendet (Ergebnisse siehe Tabelle 1.2.2).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, aqueous solutions) or dry (e.g. water-dispersible powders) formulations were diluted to the required concentrations with deionized water and sprayed onto the green parts of the plant and the uncovered areas using a water application rate of 300 liters per hectare Part of the floor surface applied. In the experiment shown below, the safeners were used as a 20 percent water-dispersible powder, the herbicide glufosinate-ammonium as a commercially available 20 percent aqueous surfactant-containing solution (for results see Table 1.2.2).
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 1.2.2: Nachauflaufanwendung: Herbizid und Safener im Tankmix- VerfahrenThe 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 1.2.2: Post-emergence application: herbicide and safener using the tank mix method
Abkürzungen: Herbizid H3 = Glufosinate-Ammonium Verb. 17 2-Hydroxyzimtsäure (vgl Tab. 1) Verb. 155 = 2,4-Dichlorzimtsäure (vgl. Tab. 1) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' CHEAL Chenopodium album AMARE Amaranthus retroflexus Abbreviations: Herbicide H3 = glufosinate ammonium Verb. 17 2-hydroxycinnamic acid (see Tab. 1) Verb. 155 = 2,4-dichlorocinnamic acid (see Tab. 1) ZEAMA Zea mays (maize), cultivar 'Lorenzo' CHEAL Chenopodium album AMARE Amaranthus retroflexus
C2) Safener als Saatgutbeizung gefolgt von HerbizidspritzapplikationC2) Safener as seed dressing followed by herbicide spray application
C2.1) SaatgutbehandlungC2.1) 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.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.
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 safeners were formulated as 20 percent water dispersible powders. These formulations were weighed in so that the required application rates (g-a.i./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.
C2.2) Vorauflaufapplikation von Herbiziden nach Saatgutbeizung mit SafenerC2.2) 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 sandigenThe seeds treated with safener and untreated seeds as controls were placed in round plastic pots with a diameter of 13 cm in a sandy
Lehmboden gesät und mit einer ca. 1 cm dicken Schicht sandigem Lehm bedeckt.Clay soil sown and covered with an approx. 1 cm thick layer of sandy loam.
Die Herbizide in Form flüssiger (z.B. Emusionskonzentrate) oder trockener (z.B. wasserdispergierbare Pulver) Formulierungen wurden auf die benötigtenThe herbicides in the form of liquid (e.g. emulsion concentrates) or dry (e.g. water-dispersible powders) formulations were adapted to the required
Konzentrationen mit deionisiertem Wasser verdünnt und mit einem Spritzschlitten unter Verwendung einer Wasseraufwandmenge von 300 Litern je Hektar auf dieConcentrations diluted with deionized water and sprayed with a sprayer using 300 liters of water per hectare
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.Applied floor surface. 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 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% = no discernible effect compared to the untreated plant, 100% = treated plant dies).
Tabelle 2.2.1 : Herbizid im Vorauflauf nach Saatgutbehandlung mit SafenerTable 2.2.1: Pre-emergence herbicide after seed treatment with safener
Abkürzungen: Herbizid H1 = Isoxaflutole Verb. 17 2-Hydroxyzimtsäure (vgl Tab. 1) Verb. 155 = 2,4-Dichlorzimtsäure (vgl. Tab. 1) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' Tabelle 2.2.2: Herbizid Vorauflaufanwendung nach Safener SaatgutbehandlungAbbreviations: herbicide H1 = isoxaflutole Verb. 17 2-hydroxycinnamic acid (see Tab. 1) Verb. 155 = 2,4-dichlorocinnamic acid (see Tab. 1) ZEAMA Zea mays (maize), variety 'Lorenzo' Table 2.2.2: Pre-emergence herbicide application after Safener seed treatment
Abkürzungen: Herbizid H1 = Isoxaflutole Verb. 17 2-Hydroxyzimtsäure (vgl Tab. 1) Verb. 155 = 2,4-Dichlorzimtsäure (vgl. Tab. 1) GLXMA Glycine max (Sojabohne), Sorte 'Lambert'Abbreviations: herbicide H1 = isoxaflutole Verb. 17 2-hydroxycinnamic acid (see Tab. 1) Verb. 155 = 2,4-dichlorocinnamic acid (see Tab. 1) GLXMA Glycine max (soybean), cultivar 'Lambert'
C2.3) Nachauflaufapplikation von Herbiziden nach Saatgutbeizung mit Safener Die mit Safener behandelten Samen und unbehandelte Samen 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 wurde das Herbizid Foramsulfuron als 20 prozentiges wasserdispergierbares Pulver verwendet (Ergebnisse siehe Tabelle 2.3.1).C2.3) Post-emergence application of herbicides after seed dressing with safener 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 approximately two to three weeks so that the plants reached a growth stage of 2 to 4 leaves. The herbicides in the form of liquid (for example emulsion concentrates) or dry (for example 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 with 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. 17 2-Hydroxyzimtsäure (vgl Tab. 1 ) Verb. 155 = 2,4-Dichlorzimtsäure (vgl. Tab. 1) ZEAMA Zea mays (Mais), Sorte 'Lorenzo' Abbreviations: herbicide H2 = foramsulfuron Verb. 17 2-hydroxycinnamic acid (see Tab. 1) Verb. 155 = 2,4-dichlorocinnamic 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,
worinwherein
R Carboxy oder ein Derivat der Carboxylgruppe, vorzugsweise einen Rest der Formel -CN oder -C(=X)-Y-R oder -C(X'R')(X"R")-Y-R in welcher R Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen heterocyclischen Rest, der unsubstituiert oder substituiert ist, oder Acyl und R', R" jeweils unabhängig voneinander Wasserstoff, (Cι-C6)Alkyl, (C2- C6)Alkenyl, (C2-C6)Alkinyl oder (Cι-C6)Alkanoyl, wobei jeder der letztgenannten 4 Reste im Alkylteil unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-Cβ)Alkoxy und (Cι-C6)Haloalkoxy substituiert ist, oder gemeinsam direkt miteinander gebunden sind und eine divalente Gruppe der Formel -CH2CH2- oder -CH2CH2CH2- oder -CH2CH2CH2CH2-, wobei jeder der letztgenannten 3 Gruppen unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C6)AIkyl, (d-C6)Haloalkyl, (C C6)Alkoxy und (d-C6)Haloalkoxy substituiert ist, X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind, X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für Wasserstoff, (d-C6)AlkyI, (Cι-C6)Haloalkyl, (Cι-C6)Hydroxyalkyl, (C1-C4)Alkoxy-(C1-C4)alkyI, (C2-C6)Alkenyl oder (C2-C6)Alkinyl steht, Y eine direkte Bindung oder eine Gruppe der Formel O, S, NR° oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind, und 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, bedeuten, R2, R3 jeweils unabhängig voneinander und im Falle, dass n = 2, 3, 4, 5 oder 6 bedeutet, jeweils unabhängig von den anderen Resten R2 und R3 Wasserstoff, Halogen, (CrC4)Alkyl, (C2-C4)AIkenyl, (C2-C4)Alkinyl, (d- C )Alkoxy, (d-C5)Alkanoyloxy oder (C1-C5)Alkanoyl, wobei jeder der letztgenannten 6 Reste unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C6)Alkoxy und (Ci-CβJHaloalkoxy substituiert ist, (R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN, einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, einen heterocyclischen Rest, der unsubstitutiert oder substitutiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, und A Wasserstoff oder einen Kohlenwasserstoffrest, der unsubstituiert oder substituiert ist, oder einen heterocyclischen Rest, der unsubstitutiert oder substitutiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, bedeuten, und m die ganze Zahl 0, 1 , 2, 3, 4 oder 5, n die ganze Zahl 1 , 2, 3, 4, 5 oder 6, bedeuten, als Safener für Kultur- oder Nutzpflanzen gegen phytotoxische Wirkungen von Agrochemikalien an diesen Pflanzen, wobei Verbindungen der Formel (!) oder deren Salze, worin R1 Carboxy, R2, R3 jeweils Wasserstoff, (R4)m einen Hydroxyrest (m = 1) in beliebiger Position oder zwei Reste R4 (m = 2) in beliebiger Position, wobei in letzterem Fall der eine Rest eine Hydroxygruppe ist und der andere Rest Hydroxy oder Methoxy bedeutet, und n die Zahl 1 bedeuten, als Safener für Kultur- oder Nutzpflanzen gegen phytotoxische Wirkungen von anderen Agrochemikalien als Glyphosate verwendet werden.R carboxy or a derivative of the carboxyl group, preferably a radical of the formula -CN or -C (= X) -YR or -C (X'R ') (X "R") - YR in which R is hydrogen or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclic radical which is unsubstituted or substituted, or acyl and R ', R "are each, independently of one another, hydrogen, (-CC 6 ) alkyl, (C 2 - C 6 ) alkenyl, (C 2 - C 6 ) alkynyl or (-C-C 6 ) alkanoyl, each of the latter 4 residues in the alkyl part unsubstituted or substituted by one or more residues from the group halogen, hydroxy, (Cι-Cβ) alkoxy and (Cι-C 6 ) haloalkoxy is, or are directly bonded together and are a divalent group of the formula -CH2CH 2 - or -CH2CH2CH2- or -CH 2 CH 2 CH 2 CH 2 -, each of the latter 3 groups being unsubstituted or by one or more radicals from the group Halogen, hydroxy, (dC 6 ) alkyl, (dC 6 ) haloalkyl, (CC 6 ) alkoxy and (dC 6 ) haloalkoxy is substituted, X a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, X ', X "each independently of one another are a divalent group of the formula O, S or NR °, where R ° is hydrogen, (dC 6 ) alkyl, (Cι-C 6 ) haloalkyl, (-C 6 -C) hydroxyalkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyI, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, Y is a direct bond or a group of the formula O, S, NR ° or NR c -NR d R e , where R c , R d and R e are as defined below, and 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 independent of R as defined for R, R 2 , R 3 each independently of one another and im If n = 2, 3, 4, 5 or 6, each independently of the other radicals R 2 and R 3 is hydrogen, halogen, (CrC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 - C 4 ) alkynyl, (d-C) alkoxy, (dC 5 ) alkanoyloxy or (C 1 -C 5 ) alkanoyl, each of the latter 6 residues unsubst itututiert or by one or more residues from the group halogen, hydroxy, (dC 6 ) alkoxy and (Ci-CβJHaloalkoxy is substituted, (R 4 ) m m residues R 4 , wherein each of the residues R 4 independently from the group of the residues Halogen, SCN, CN, a hydrocarbon radical which is unsubstituted or substituted, a heterocyclic radical which is unsubstituted or substituted, and radicals of the formula -Z * -A, where Z * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and A is hydrogen or a hydrocarbon radical that is unsubstituted or substituted, or a heterocyclic radical that is unsubstituted or substituted, or an acyl radical, provided that Z * in the case A = acyl can only be O or S, and m is the integer 0, 1, 2, 3, 4 or 5, n denotes the integer 1, 2, 3, 4, 5 or 6, as a safener for crops or crop plants against phytotoxic effects of agrochemicals on these plants, where compounds of the formula (!) or their salts, in which R 1 is carboxy, R 2 , R 3 are each hydrogen, (R 4 ) m is a hydroxy radical (m = 1) in any position or two radicals R 4 (m = 2) in any position, in the latter case one radical being a hydroxyl group and the other The remainder is hydroxy or methoxy, and n is the number 1, are used as safeners for crops or crop plants against phytotoxic effects of agrochemicals other than glyphosate.
2. Verwendung nach Anspruch 1 , dadurch gekennzeichnet, dass R Wasserstoff, (d-C18)AlkyI, (C2-C18)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl, (C5-C9)Cycloalkenyl, (C3-C9)CycIoalkyI-(C1-C12)alkyl, Phenyl, Phenyl- (Cι-C12)alkyl, Heterocyclyl oder Heterocyclyl-(C1-Ci2)aIkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, Thiocyanato, (C1-C4)Alkoxy, (Cι-C4)Haloalkoxy, (C2- C )Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C )AlkyIthio, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (C1-C4)Haloalkylsulfinyl, (d- dJHaloalkyisulfonyl, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (C C4)A!kanoyl, (d-C4)Haloalkanoyl, [(d-C )Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (CrC4)Alkyl und (d-C4)Haloalkyl substituiert ist, oder (Ct-C6)Alkanoyl, (d-C4)Haloalkanoyl, [(d-C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (Cι-C4)alkyl]-carbonyl, [Phenyl-(C1-C4)alkoxy]-carbonyl, wobei jeder der letztgenannten 4 Reste im Phenylring unsubstituiert oder substituiert ist, Aminocarbonyl, Mono[(Cι-C4)alkylamino]-carbonyl, Di[(d-C4)alkylamino]- carbonyl, (d-C4)AlkylsuIfinyl, (Cι-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl oder (d-C )Haloalkylsulfonyl, wobei R inklusive Substituenten 1 bis 30 C-Atome aufweist, und R', R" jeweils unabhängig voneinander (d-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl oder (CrC6)Alkanoyl, wobei jeder der letztgenannten 4 Reste unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (C-i-CβJAlkoxy und (Cι-Ce)Haloalkoxy substituiert ist, oder gemeinsam direkt miteinander gebunden sind und eine divalente Gruppe der Formel -CH2CH2- oder -CH2CH2CH2- oder -CH2CH2CH2CH2-, wobei jeder der letztgenannten 3 Gruppen unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (Cι-C4)Alkyl, (d-C )Haloalkyl, (d- C4)Alkoxy und (d-C )Haloalkoxy substituiert ist,2. Use according to claim 1, characterized in that R is hydrogen, (dC 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 ) cycloalkyI- (C 1 -C 12 ) alkyl, phenyl, phenyl- (-C-C 12 ) alkyl, heterocyclyl or heterocyclyl- (C 1 -Ci 2 ) aIkyl, where each of the last 10 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (C 1 -C 4 ) alkoxy, (Cι-C 4 ) haloalkoxy, (C 2 - C) Alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC) alkyIthio, (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (C 1 -C 4 ) haloalkylsulfinyl, (d- dJHaloalkyisulfonyl, mono (Cι-C4) alkylamino, di (Cι-C 4 ) alkylamino, (CC 4 ) A! kanoyl, (dC 4 ) haloalkanoyl, [(dC) alkoxy] carbonyl, [(Cι-C4) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι- C 4 ) alkylamino] - carbonyl, di [(Cι-C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (CrC 4 ) alkyl and (dC 4 ) haloalkyl is substituted, or (Ct-C 6 ) A lkanoyl, (dC 4 ) haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(Cι-C 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [phenyl- (-C-C 4 ) alkyl] -carbonyl, [phenyl- (C 1 -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 4 ) alkylamino] carbonyl, (dC 4 ) alkylsulifinyl, (Cι-C 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl or (dC) haloalkylsulfonyl, where R including substituents has 1 to 30 carbon atoms , and R ', R "each independently of one another (dC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl or (CrC 6 ) alkanoyl, each of the latter 4 residues being unsubstituted or by one or more radicals from the group halogen, hydroxy, (Ci-CβJalkoxy and (-C-Ce) haloalkoxy is substituted, or are bonded together directly and form a divalent group of the formula -CH 2 CH 2 - or -CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH2-, where each of the latter 3 groups unsubstituted or by one or more radicals from the group halogen, hydroxy, (-C-C 4 ) alkyl, (dC) haloalk yl, (d- C 4 ) alkoxy and (dC) haloalkoxy is substituted,
X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind, X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für Wasserstoff, (d-C4)Alkyl, (d-C4)Haloalkyl, (d- C4)Hydroxyalkyl, (Cι-C4)Alkoxy-(C1-C4)alkyl, (C2-C4)Alkenyl oder (C2- C4)Alkinyl steht, Y eine direkte Bindung oder eine divalente Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei Rc, Rd und Re wie unten definiert sind, und 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, R2, R3 jeweils unabhängig voneinander und im Falle, dass n = 2, 3, 4, 5 oder 6 bedeutet, jeweils unabhängig von den anderen Resten R2 und R3 Wasserstoff, (C1-C2)Alkyl, (C1-C2)Alkoxy oder (Cι-C3)Alkanoyloxy, wobei jeder der letztgenannte 3 Reste im Alkylteil unsubstitutiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C6)Alkoxy und (Cr C6)Haloalkoxy substituiert ist, (R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN und (Cι-Cι8)Alkyl, (C2-C18)Alkenyl, (C2-C18)Alkinyl, (C3-C9)Cycloalkyl, (C5- C9)Cycloalkenyl, (C3-C9)Cycloalkyl-(Cι-d2)alkyl, Phenyl, Phenyl-(d-d2)alkyl, Heterocyclyl und Heterocyclyl-(Cι-Cι2)a!kyl, 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, (d-C4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (d-C4)Alkylthio, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)HaloalkylsuIfonyl, Mono(d-C4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (d-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(Cι-C )Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (d-C )Alkyl und (d-C4)Haloalkyl substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, und A Wasserstoff oder (d-Cι8)Alkyl, (C2-C18)Alkenyl, (C2-d8)Alkinyl, (C3-C9)Cycloalkyl, (C5- C9)Cycloalkenyl, (C3-C9)CycIoalkyl-(C1-C12)alkyl, Phenyl, Phenyl- (Cι-C12)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, (C1-C4)Alkoxy, (d-C4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C )Haloalkenyloxy, (C C4)Alkylthio, (d- C4)Alkylsulfinyl, (d-C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)Haloalkylsulfonyl, Mono(CrC4)alkylamino, Di(d-C4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(Cι-C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(C1-C )alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C4)Alkyl und (Cι-C )Haloalkyl substituiert ist, oder einen Acylrest, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, bedeuten, wobei jeder Rest R4 inklusive Substituenten 1 bis 30 C-Atome aufweist, und m die ganze Zahl 0, 1 , 2, 3, 4 oder 5 und n die ganze Zahl 1 , 2, 3, 4, 5 oder 6, bedeuten.X is a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, X ', X "are each independently a divalent group of the formula O, S or NR ° , where R ° is hydrogen, (dC 4 ) alkyl, (dC 4 ) haloalkyl, (d- C 4 ) hydroxyalkyl, (Cι-C 4 ) alkoxy- (C 1 -C 4 ) alkyl, (C 2 -C 4 ) Alkenyl or (C 2 - C 4 ) alkynyl, Y is a direct bond or a divalent 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 and R a , R b , R c , R d and R e in the radicals X and Y each independently of one another 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, R 2 , R 3 are each independently of one another and in the case where n = 2, 3, 4, 5 or 6, in each case independently of the other radicals R 2 and R 3 is hydrogen, (C 1 -C 2 ) alkyl, (C 1 -C 2 ) alkoxy or (-C-C 3 ) alkanoyloxy, each of the latter 3 residues in the alkylte is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (dC 6 ) alkoxy and (Cr C 6 ) haloalkoxy, (R 4 ) m m radicals R 4 , each of the radicals R 4 independently of one another from the group consisting of halogen, SCN, CN and (-C 1 -C 8 ) 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- (Cι-d 2 ) alkyl, phenyl, phenyl- (dd 2 ) alkyl, Heterocyclyl and heterocyclyl- (-Cι-Cι 2 ) a! Kyl, each of the latter 10 residues unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (Cι-C 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (d- C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) HaloalkylsuIfonyl, mono (dC 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (dC 4 ) haloalkanoyl, [(CC 4 ) alkoxy] carbonyl, [(Cι -C) Haloalkoxy] carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] carbonyl, di [(-C-C 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (dC) alkyl and (dC 4 ) haloa lkyl is substituted, and radicals of the formula -Z * -A is selected, where Z * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and A is hydrogen or (d -CC 8 ) Alkyl, (C 2 -C 18 ) alkenyl, (C 2 -d 8 ) alkynyl, (C 3 -C 9 ) cycloalkyl, (C 5 - C 9 ) cycloalkenyl, (C 3 -C 9 ) cycloalkyl- (C 1 -C 12 ) alkyl, phenyl, phenyl- (-C-C 12 ) 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 1 -C 4 ) alkoxy, (dC 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C) haloalkenyloxy, (CC 4 ) alkylthio, (d- C 4 ) Alkylsulfinyl, (dC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (CrC 4 ) alkylamino, di (dC 4 ) alkylamino, (Cι-C 4 ) alkanoyl, (Cι-C 4 ) Haloalkanoyl, [(CC 4 ) alkoxy] carbonyl, [(-C-C 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(C 1 -C) alkylamino] carbonyl and in the fall le cyclic radicals are also substituted by (C 1 -C 4 ) alkyl and (C 1 -C) haloalkyl, or an acyl radical, provided that Z * in the case A = acyl can only be O or S, where each radical R 4, including substituents, has 1 to 30 C atoms, and m is the integer 0, 1, 2, 3 , 4 or 5 and n are the integer 1, 2, 3, 4, 5 or 6.
3. Verwendung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass R1 einen Rest der Formel -C(=X)-Y-R oder -C(X'R')(X"R")-Y-R bedeutet, in welcher3. Use according to claim 1 or 2, characterized in that R 1 is a radical of the formula -C (= X) -YR or -C (X'R ') (X "R") - YR, in which
R Wasserstoff, (C C12)Alkyl, (C2-d2)Alkenyl, (C2-C12)Alkinyl, (C3-C6)Cycloalkyl, (C5-C6)Cycloalkenyl, (C3-C6)Cycloa!kyl-(C1-C4)alkyl, Phenyl, Phenyl- (d-djalkyl, Heterocyclyl oder Heterocyclyl-(Cι-C )alkyl, wobei jeder der letztgenannten 10 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-dJAlkoxy, (d- C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (Cι-C4)Alkylthio, (d-C4)Alkylsulfinyl, (C C4)Alkylsulfonyl, (d-C4)Haloalkylsulfinyl, (d- C )HaloalkylsuIfonyl, Mono(C -C4)alkylamino, Di(C1-C4)alkyIamino, (C1-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(Cι-C )alkylamino]-carbonyl und im Falle cyclischer Reste auch (d-C4)Alkyl und (Cι-C4)Haloaikyl substituiert ist, oder (Cι-C4)Alkanoyl, (Cι-C4)Haloalkanoyl, [(Cι-C )Alkoxy]carbonyl, [(C1-C )Haloalkoxy]carbonyl, Phenylcarbonyl, Phenoxycarbonyl, [Phenyl- (d-djalkylj-carbonyl, [Phenyl-(Cι-C4)alkoxy]-carbonyl, Aminocarbonyl, Mono[(CrC4)alkylamino]-carbonyl, Di[(Cι-C4)alkylamino]-carbonyl, (d- C4)Alkylsulfinyl, (CrC4)Alkylsulfonyl, (C C4)Haloalkylsulfinyl oder (d- C4)Haloalkylsulfonyl,R is hydrogen, (CC 12 ) alkyl, (C 2 -d 2 ) alkenyl, (C 2 -C 12 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 -C 6 ) Cyclo! Kyl- (C 1 -C 4 ) alkyl, phenyl, phenyl- (d-djalkyl, heterocyclyl or heterocyclyl- (Cι-C) alkyl, each of the latter 10 residues unsubstituted or by one or more residues from the Halogen, hydroxy group, (d-dJalkoxy, (d- C 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (Cι-C 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C) haloalkylsulfonyl, mono (C -C 4 ) alkylamino, di (C 1 -C 4 ) alkyIamino, (C 1 -C 4 ) alkanoyl, (Cι- C 4 ) haloalkanoyl, [(CC 4 ) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(Cι-C) alkylamino] carbonyl and in the case of cyclic radicals also (dC 4 ) alkyl and (Cι-C 4 ) haloaikyl is substituted, or (Cι-C 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C) alkoxy] carbonyl, [( C 1 -C) haloalkoxy] carbonyl, phenylcarbo nyl, phenoxycarbonyl, [phenyl- (d-djalkylj-carbonyl, [phenyl- (Cι-C 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(CrC 4 ) alkylamino] -carbonyl, di [(Cι-C 4 ) alkylamino ] -carbonyl, (d- C 4 ) alkylsulfinyl, (CrC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl or (d- C 4 ) haloalkylsulfonyl,
X eine divalente Gruppe der Formel O, S oder NRa oder N-NRaRb, wobei Ra und Rb wie unten definiert sind, X', X" jeweils unabhängig voneinander eine divalente Gruppe der Formel O, S oder NR°, wobei R° für Wasserstoff, (C C4)AlkyI, (C C4)Haloalkyl, (C C4)Hydroxyalkyl, (C2-C4)Alkenyl oder (C2-C4)Alkinyl steht, Y eine direkte Bindung oder eine divalente Gruppe der Formel O, S, NRC oder NRc-NRdRe, wobei R.c, Rd und Re wie unten definiert sind, undX is a divalent group of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below, X ', X "each independently represent a divalent group of the formula O, S or NR °, where R ° is hydrogen, (CC 4 ) alkyl, (CC 4 ) haloalkyl, (CC 4 ) hydroxyalkyl, (C 2 -C 4 ) Alkenyl or (C 2 -C 4 ) alkynyl, Y is a direct bond or a divalent 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 below are defined, and
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, (R4)m m Reste R4, wobei jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen, SCN, CN und (d-C6)Alkyl, (C2-C6)Alkenyl, (C2-C6)AlkinyI, (C3-C6)Cycloalkyl, (C3-C6)Cycloalkyl-(CrC4)alkyl, Phenyl, Phenyl-(C C4)alkyl, Heterocyclyl und Heterocyclyl-(.Cι-C4)alkyl, wobei jeder der letztgenannten 9 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Amino, Cyano, Nitro, (d-d)Alkoxy, (C C4)Haloalkoxy, (C2-C4)Alkenyloxy, (C2- C4)Haloalkenyloxy, (d-C4)Alkylthio, (d-C4)Alkylsulfinyl, (d- C4)Alkylsulfonyl, (Cι-C4)Haloalkylsulfinyl, (Cι-C4)Haloalkylsulfonyl, Mono(C C4)alkylamino, Di(Cι-C4)alkylamino, (Cι-C4)Alkanoyl, (Cι-C4)HaloaIkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(CrC4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C )alkylamino]- carbonyl, Di[(Cι-C4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-C )Alkyl und (d-C4)Haloalkyl substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei Z* eine Gruppe der Formel O oder S(O)x , wobei x = 0, 1 oder 2 ist, und A Wasserstoff oder (d-C8)Alkyl, (C2-C8)AIkenyl, (C2-C8)Alkinyl, (C3-C6)Cycloalkyl, (C5- C6)Cycloalkenyl, (C3-C6)Cycloalkyl-(d-C6)aIkyl, Phenyl, Phenyl- (d-Ce)alkyl, Heterocyclyl oder Heterocyclyl-(Cι-C6)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, (d-C4)Haloalkoxy, (C2- C4)Alkenyloxy, (C2-C4)Haloalkenyloxy, (C1-C4)Alkylthio, (d- C4)Alkylsulfinyl, (d-C4)Alky!sulfonyl, (d-C4)Haloalkylsulfinyl, (d- C4)HaloaIkylsulfonyl, Mono(Cι-C4)alkylamino, Di(Cι-C4)alkylamino, (d-C4)Alkanoyl,_ (d-C4)Haloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(C C4)Haloalkoxy]carbonyl, Aminocarbonyl, Mono[(Cι-C4)alkylamino]- carbonyl, Di[(CrC4)alkylamino]-carbonyl und im Falle cyclischer Reste auch (Cι-d)Alkyl und (Cι-C4)Haloalkyl substituiert ist, oder, vorausgesetzt, dass Z* im Falle A = Acyl nur O oder S sein kann, einen Acylrest aus der Gruppe, die aus den Resten (C1-C4)Alkanoyl, (d-dJHaloalkanoyl, [(Cι-C4)Alkoxy]carbonyl, [(d-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 durch einen oder mehrere Reste aus der Gruppe Halogen, (d- C4)Alkyl, (C C4)Alkoxy, (CrC4)Haloalkyl, (d-C4)Haloalkoxy und (d- C4)Alkylthio substituiert ist, besteht, bedeuten. bedeuten.R a , R b , R c , R d and R e in the radicals X and Y are 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 for R. is defined, (R 4 ) m m radicals R 4 , each of the radicals R 4 independently of one another from the group consisting of halogen, SCN, CN and (dC 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) AlkinyI, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (CrC 4 ) alkyl, phenyl, phenyl- (CC 4 ) alkyl, heterocyclyl and heterocyclyl - (. -Cι-C 4 ) alkyl, each of the latter 9 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, amino, cyano, nitro, (dd) alkoxy, (CC 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, ( C 2 - C 4 ) haloalkenyloxy, (dC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (d- C 4 ) alkylsulfonyl, (Cι-C 4 ) haloalkylsulfinyl, (Cι-C 4 ) haloalkylsulfonyl, mono (CC 4 ) alkylamino , Di (-C-C 4 ) alkylamino, (-C-C 4 ) alkanoyl, (Cι-C 4 ) haloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(CrC 4 ) halo alkoxy] carbonyl, aminocarbonyl, mono [(-C-C) alkylamino] - carbonyl, di [(Cι-C 4 ) alkylamino] -carbonyl and in the case of cyclic radicals also (-C-C) alkyl and (dC 4 ) haloalkyl is substituted , and radicals of the formula -Z * -A is selected, where Z * is a group of the formula O or S (O) x , where x = 0, 1 or 2, and A is hydrogen or (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 - C 6 ) cycloalkenyl, (C 3 -C 6 ) cycloalkyl- (dC 6 ) alkyl, phenyl , Phenyl- (d-Ce) alkyl, heterocyclyl or heterocyclyl- (-C-C 6 ) 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, (dC 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (C 1 -C 4 ) alkylthio, (d- C 4 ) Alkylsulfinyl, (dC 4 ) alky! Sulfonyl, (dC 4 ) haloalkylsulfinyl, (d- C 4 ) haloalkylsulfonyl, mono (Cι-C 4 ) alkylamino, di (Cι-C 4 ) alkylamino, (dC 4 ) alkanoyl, _ ( dC 4 ) haloalkanoyl, [(-C-C 4 ) alkoxy] carbonyl, [(C C4) haloalkoxy] carbonyl, aminocarbonyl, mono [(Cι-C 4 ) alkylamino] carbonyl, di [(CrC 4 ) alkylamino] carbonyl and in the case of cyclic radicals also (Cι-d) alkyl and (Cι-C4) haloalkyl is substituted, or, provided that Z * in the case A = acyl can only be O or S, an acyl radical from the group consisting of the Residues (C 1 -C 4 ) alkanoyl, (d-dJHaloalkanoyl, [(Cι-C 4 ) alkoxy] carbonyl, [(dC 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 by one or more radicals from the group halogen , (d- C 4 ) alkyl, (CC 4 ) alkoxy, (C r C 4 ) haloalkyl, (dC 4 ) haloalkoxy and (d- C 4 ) alkylthio is substituted. mean.
4. Verwendung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass als Verbindungen der Formel (I) Verbindungen der Formeln (1-1) oder deren Salze,4. Use according to one of claims 1 to 3, characterized in that as compounds of the formula (I) compounds of the formulas (1-1) or their salts,
worin R1, R2, R3, R4 und m wie in Formel (I) definiert sind, verwendet werden. wherein R 1 , R 2 , R 3 , R 4 and m are as defined in formula (I) can be used.
5. Verwendung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass jeder der Reste R4 unabhängig voneinander aus der Gruppe der Reste Halogen und (d-C )Alkyl, das unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, (d-C )Alkoxy und (Cι-C4)Haloalkoxy substituiert ist, und Reste der Formel -Z*-A ausgewählt ist, wobei5. Use according to one of claims 1 to 4, characterized in that each of the radicals R 4 independently of one another from the group of the radicals halogen and (dC) alkyl which is unsubstituted or by one or more radicals from the group halogen, hydroxy, ( dC) alkoxy and (-C-C 4 ) haloalkoxy is substituted, and radicals of the formula -Z * -A is selected, wherein
Z* eine Gruppe der Formel O oder S, undZ * is a group of the formula O or S, and
A Wasserstoff oder (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, (d-C4)Alkoxy, (d- C^Haloalkoxy, (C C4)Alkylthio, (C1-C4)Alkylsulfinyl, (Cι-C4)Alkylsulfonyl, (d-C )Alkanoyl, (Cι-C )Haloalkanoyl, [(CrdJAlkoxyJcarbonyl und im Falle cyclischer Reste auch (d-dJAlkyl und (Cι-C4)Haloalkyl substituiert ist, oder einen Acylrest aus der Gruppe, die aus den Resten (Ci-dJAlkanoyl, (Cι-C4)Haloalkanoyl, [(C C4)Alkoxy]carbonyl, [(d-C4)Haloalkoxy]carbonyl besteht, bedeuten.A is hydrogen or (dC 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 radicals the group halogen, hydroxy, (dC 4 ) alkoxy, (d- C ^ haloalkoxy, (CC 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (Cι-C 4 ) alkylsulfonyl, (dC) alkanoyl, (Cι- C) Haloalkanoyl, [(CrdJAlkoxyJcarbonyl and in the case of cyclic radicals also (d-dJAlkyl and (Cι-C 4 ) haloalkyl is substituted, or an acyl radical from the group consisting of the residues (Ci-dJAlkanoyl, (Cι-C 4 ) Haloalkanoyl, [(CC 4 ) alkoxy] carbonyl, [(dC 4 ) haloalkoxy] carbonyl.
6. Verwendung nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass die Verbindungen der Formel (I) oder deren Salze als Safener gegen phytotoxische Wirkungen von Agrochemikalien an diesen Pflanzen eingesetzt werden.6. Use according to any one of claims 1 to 5, characterized in that the compounds of formula (I) or their salts are used as safeners against phytotoxic effects of agrochemicals on these plants.
7. Verwendung nach Anspruch 6, dadurch gekennzeichnet, dass die7. Use according to claim 6, characterized in that the
Verbindungen der Formel (I) oder deren Salze als Safener gegen phytotoxische Wirkungen von Pestiziden aus der Gruppe der Herbizide, Insektizide, Akarizide, Nematizide und Fungizide eingesetzt werden.Compounds of formula (I) or their salts are used as safeners against phytotoxic effects of pesticides from the group of herbicides, insecticides, acaricides, nematicides and fungicides.
8. Verfahren zum Schützen von Nutz- oder Kulturpflanzen vor phytotoxischen Nebenwirkungen von Agrochemikalien, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehrerer Verbindungen der Formel (I) oder deren Salze, wie sie nach einem der Ansprüche 1 bis 5 definiert sind, vor, nach oder gleichzeitig mit der oder den Agrochemikalien auf die Pflanzen, Pflanzenteile, Pflanzensamen oder das Saatgut appliziert.8. 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) or their Salts as defined according to any one of claims 1 to 5, applied before, after or simultaneously with the agrochemical or agrochemicals to the plants, parts of plants, plant seeds or the seeds.
9. Verfahren nach Anspruch 8, dadurch gekennzeichnet, dass die Applikation im Nachauflaufverfahren erfolgt.9. The method according to claim 8, characterized in that the application takes place in the post-emergence process.
10. Verfahren nach Anspruch 8, dadurch gekennzeichnet, dass die Applikation durch Behandlung der Pflanzensamen oder des Saatguts erfolgt.10. The method according to claim 8, characterized in that the application is carried out by treating the plant seeds or the seeds.
11. Verfahren nach Anspruch 8, dadurch gekennzeichnet, dass die Applikation im Vorauflaufverfahren erfolgt.11. The method according to claim 8, characterized in that the application takes place in the pre-emergence process.
12. Pflanzenschutzmittel, dadurch gekennzeichnet, dass es Verbindungen der Formel (I) oder deren Salze, wie sie nach einem der Ansprüche 1 bis 5 definiert sind, und Formulierungshilfsmittel enthält.12. Plant protection product, characterized in that it contains compounds of the formula (I) or their salts, as defined in any of claims 1 to 5, and formulation auxiliaries.
13. Pflanzenschutzmittel nach Anspruch 12, dadurch gekennzeichnet, dass es zusätzlich ein oder mehrere Agrochemikalien enthält. 13. Plant protection product according to claim 12, characterized in that it additionally contains one or more agrochemicals.
EP04763519A 2003-08-05 2004-07-23 Safener based on aromatic-aliphatic carboxylic acid derivatives Withdrawn EP1653806A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10335725A DE10335725A1 (en) 2003-08-05 2003-08-05 Safener based on aromatic-aliphatic carboxylic acid derivatives
PCT/EP2004/008382 WO2005016001A1 (en) 2003-08-05 2004-07-23 Safener based on aromatic-aliphatic carboxylic acid derivatives

Publications (1)

Publication Number Publication Date
EP1653806A1 true EP1653806A1 (en) 2006-05-10

Family

ID=34111911

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04763519A Withdrawn EP1653806A1 (en) 2003-08-05 2004-07-23 Safener based on aromatic-aliphatic carboxylic acid derivatives

Country Status (18)

Country Link
US (1) US7838463B2 (en)
EP (1) EP1653806A1 (en)
JP (1) JP4913592B2 (en)
KR (1) KR20060120576A (en)
CN (1) CN1829442B (en)
AR (1) AR045202A1 (en)
AU (1) AU2004264657B2 (en)
BR (1) BRPI0413358A (en)
CA (1) CA2534744A1 (en)
CR (1) CR8218A (en)
DE (1) DE10335725A1 (en)
EA (1) EA011453B1 (en)
IL (1) IL173467A0 (en)
MX (1) MXPA06001422A (en)
RS (1) RS20060038A (en)
UA (1) UA89034C2 (en)
WO (1) WO2005016001A1 (en)
ZA (1) ZA200600085B (en)

Families Citing this family (274)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2206703A1 (en) * 2008-12-30 2010-07-14 Bayer CropScience AG Pyrimidine derivatives and use thereof for combating undesired plant growth
DE102004049041A1 (en) * 2004-10-08 2006-04-13 Bayer Cropscience Ag Fungicidal drug combinations
US7652041B2 (en) * 2005-01-14 2010-01-26 Millennium Pharmaceuticals, Inc. Cinnamide and hydrocinnamide derivatives with kinase inhibitory activity
JP5205063B2 (en) 2006-02-08 2013-06-05 クミアイ化学工業株式会社 A phytotoxicity reducing agent for field cultivation herbicide and a phytotoxicity reducing method using the same
US7951995B2 (en) 2006-06-28 2011-05-31 Pioneer Hi-Bred International, Inc. Soybean event 3560.4.3.5 and compositions and methods for the identification and detection thereof
BR122017006111B8 (en) 2006-10-31 2022-12-06 Du Pont METHODS TO CONTROL WEEDS
EP2052608A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052612A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052615A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052603A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Application of 2-lodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzol sulphonamide and/or its salts for inhibiting unwanted plant growth in selected agricultural crop cultures or non-cultivated land
EP2052613A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052609A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052611A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052610A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052606A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052605A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052614A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052607A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide combination
EP2052616A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Herbicide safener combination
EP2052604A1 (en) 2007-10-24 2009-04-29 Bayer CropScience AG Salts of 2-lodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzol sulphonamide, method for its manufacture and its application as herbicide and plant growth regulator
EP2064953A1 (en) 2007-11-29 2009-06-03 Bayer CropScience AG Herbicide azole combination
DE102008006005A1 (en) 2008-01-25 2009-07-30 Bayer Cropscience Ag New N-azinyl-N'-pyridylsulfonyl-urea compounds useful e.g. as herbicide, plant growth regulator and plant protection regulator and to combat undesirable plant growth e.g. Agrostis in special plant cultures e.g. wheat, barley and rye
EP2072512A1 (en) 2007-12-20 2009-06-24 Bayer CropScience AG Herbicide compounds based on N-Azinyl-N'-pyridylsulfonyl-ureas
EP2103216A1 (en) 2008-03-19 2009-09-23 Bayer CropScience AG Selected salts from 3-(5,6-dihydro-1,4,2-dioxazin-3-yl)-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl] pyridine-2-sulfonamide, methods for their production and their usage as herbicides and plant growth regulators
EP2110019A1 (en) 2008-04-19 2009-10-21 Bayer CropScience AG Herbicidal compounds based on N-Azinyl-N'-phenylsulfonylureas
EP2112143A1 (en) 2008-04-22 2009-10-28 Bayer CropScience AG 2-(benzylsulfonyl)-oxazol-derivatives, chiral 2-(benzylsulfinyl]-oxazol derivatives, 2-(benzylsulfanyl-oxazol) derivatives, process for their preparation, as well as their use as herbicide and plant growth regulators
EP2112149A1 (en) 2008-04-22 2009-10-28 Bayer CropScience Aktiengesellschaft 2-[(1H-Pyrazol-4-ylmethyl)-sulfonyl]-oxazole derivatives, 2-[(1H-pyrazol-4-ylmethyl)-sulfanyl]-oxazole derivatives and chiral 2-[(1H-pyrazol-4-ylmethyl)-sulfinyl]-oxazole derivatives, method for production of same and their use as herbicides and plant growth regulators
EP2135865A1 (en) 2008-06-17 2009-12-23 Bayer CropScience AG Substituted 1-(diazinyl)pyrazol-4-yl acetic acids, method for their production and their use as herbicides and plant growth regulators
EP2147919A1 (en) 2008-07-24 2010-01-27 Bayer CropScience Aktiengesellschaft Heterocyclic substituted amides, method for their manufacture and their use as herbicides
DE102008037627A1 (en) * 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides
US8367873B2 (en) * 2008-10-10 2013-02-05 Bayer Cropscience Ag Phenyl-substituted bicyclooctane-1,3-dione derivatives
EP2191716A1 (en) 2008-11-29 2010-06-02 Bayer CropScience AG Herbicide safener combination
EP2191719A1 (en) 2008-11-29 2010-06-02 Bayer CropScience AG Herbicide safener combination
EP2191720A1 (en) 2008-11-29 2010-06-02 Bayer CropScience AG Herbicide-safener combination
EP2210492A1 (en) 2008-11-29 2010-07-28 Bayer CropScience AG Herbicide safener combination
US8389443B2 (en) 2008-12-02 2013-03-05 Bayer Cropscience Ag Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives
US8846946B2 (en) 2008-12-02 2014-09-30 Bayer Cropscience Ag Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives
EP2194052A1 (en) 2008-12-06 2010-06-09 Bayer CropScience AG Substituted 1.(1-thiazolyl)- and 1-(isothiazolyl)pyrazol-4-yl acetic acids, method for their production and their use as herbicides and plant growth regulators
EP2210879A1 (en) 2008-12-30 2010-07-28 Bayer CropScience AG Pyrimidine derivatives and use thereof for combating undesired plant growth
AR075573A1 (en) * 2009-02-11 2011-04-20 Basf Se DIMETHOMORPH AS A PESTICIDE PROTECTOR WITH PHYTO-TOXIC EFFECTS
MX2011009188A (en) 2009-03-11 2011-09-26 Bayer Cropscience Ag Halogenalkylmethylenoxy-phenyl-substituted ketoenols.
EP2229813A1 (en) 2009-03-21 2010-09-22 Bayer CropScience AG Pyrimidine-4-ylpropandinitrile derivatives, method for their manufacture and their use as herbicides and plant growth regulators
AR076224A1 (en) * 2009-04-22 2011-05-26 Bayer Cropscience Ag USE OF PROPINEB AS A BIRD REPELLENT
EP2245935A1 (en) 2009-05-02 2010-11-03 Bayer CropScience AG Herbicide compounds based on N-Azinyl-N-pyridylsulfonyl-uric substances
ES2525014T3 (en) 2009-05-19 2014-12-17 Bayer Cropscience Ag Herbicidal spiroheterocyclic tetronic acid derivatives
WO2011039276A1 (en) 2009-10-01 2011-04-07 Bayer Cropscience Ag Oxathiazinyl(het)arylsulfonylureas, processes and intermediates for preparation thereof and use thereof as crop protection agents and crop growth regulators
EP2327700A1 (en) 2009-11-21 2011-06-01 Bayer CropScience AG Dialkyl triazinamines and use thereof for combating undesired plant growth
WO2011073098A1 (en) 2009-12-15 2011-06-23 Bayer Cropscience Ag 1-(heteroaryl)-pyrazol-4-yl-acetic acids, method for the production thereof, and the use thereof as herbicides and plant growth regulators
ES2659085T3 (en) 2009-12-23 2018-03-13 Bayer Intellectual Property Gmbh HPPD Inhibitor Herbicide Tolerant Plants
BR112012015690A2 (en) 2009-12-23 2015-08-25 Bayer Intelectual Property Gmbh Herbicide tolerant plants of hppd inhibitors.
AR079882A1 (en) 2009-12-23 2012-02-29 Bayer Cropscience Ag TOLERANT PLANTS TO INHIBITING HERBICIDES OF HPPD
CA2785208A1 (en) 2009-12-23 2011-06-30 Bayer Intellectual Property Gmbh Plants tolerant to hppd inhibitor herbicides
BR112012015692A2 (en) 2009-12-23 2015-08-25 Bayer Intelectual Property Gmbh Hppds inhibitor herbicide tolerant plants.
CN102711461A (en) 2009-12-29 2012-10-03 Mapi医药公司 Intermediate compounds and processes for the preparation of tapentadol and related compounds
ES2545113T3 (en) * 2010-02-10 2015-09-08 Bayer Intellectual Property Gmbh Tetramic acid derivatives substituted in a spiroheterocyclic manner
WO2011098440A2 (en) 2010-02-10 2011-08-18 Bayer Cropscience Ag Biphenyl substituted cyclical keto-enols
WO2011107443A1 (en) 2010-03-02 2011-09-09 Bayer Cropscience Ag Use of propineb for physiological curative treatment under zinc deficiency
JP2013521255A (en) 2010-03-04 2013-06-10 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング Fluoroalkyl-substituted 2-amidobenzimidazoles and their use to enhance stress tolerance in plants
WO2011107445A1 (en) 2010-03-04 2011-09-09 Bayer Cropscience Ag Hydrate and anhydrous crystal form of the sodium salt of 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]benzene­sulfonamide, process for preparation thereof and use thereof as herbicides and plant growth regulators
EP2371823A1 (en) 2010-04-01 2011-10-05 Bayer CropScience AG Cyclopropyl-substituted phenylsulfonylamino(thio)carbonyltriazolinones, their production and use as herbicides and plant growth regulators
AR080827A1 (en) 2010-04-06 2012-05-09 Bayer Cropscience Ag USE OF ACID 4- PHENYL-BUTIRICO AND / OR ITS SALTS FOR THE INCREASE OF STRESS TOLERANCE IN PLANTS
AU2011237909B2 (en) 2010-04-09 2015-08-20 Bayer Intellectual Property Gmbh Use of derivatives of the (1-cyanocyclopropyl)phenylphosphinic acid, the esters thereof and/or the salts thereof for enhancing the tolerance of plants to abiotic stress
WO2011138280A2 (en) 2010-05-04 2011-11-10 Bayer Cropscience Ag Herbicide/safener combinations comprising arylpyridazinones and safener
BR112013003135A2 (en) 2010-08-13 2017-11-07 Pioneer Hi Bred Int isolated or recombinant polynucleotide and polypeptide, nucleic acid construct, cell, plant, plant explant, transgenic seed, plant cell production method for weed control and detection of an hppd polypeptide and a polynucleotide.
BR112013005223A2 (en) 2010-09-03 2016-05-03 Bayer Ip Gmbh "Substituted fused pyrimidinones and dihydropyrimidinones."
EP2460406A1 (en) 2010-12-01 2012-06-06 Bayer CropScience AG Use of fluopyram for controlling nematodes in nematode resistant crops
WO2012038476A1 (en) 2010-09-22 2012-03-29 Bayer Cropscience Ag Use of active ingredients for controlling nematodes in nematode-resistant crops
WO2012052410A1 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Novel substituted picolinic acids, salts and acid derivatives thereof, and use thereof as herbicides
CN103339096A (en) 2010-11-02 2013-10-02 拜耳知识产权有限责任公司 Phenyl-substituted bicyclooctane-1,3-dione-derivatives
CA2810180C (en) 2010-11-24 2015-07-28 Pioneer Hi-Bred International, Inc. Brassica gat event dp-073496-4 and compositions and methods for the identification and/or detection thereof
WO2012071039A1 (en) 2010-11-24 2012-05-31 Pioner Hi-Bred International, Inc. Brassica gat event dp-061061-7 and compositions and methods for the identification and/or detection thereof
CN103281900A (en) 2010-12-01 2013-09-04 拜耳知识产权有限责任公司 Use of fluopyram for controlling nematodes in crops and for increasing yield
TWI667347B (en) 2010-12-15 2019-08-01 瑞士商先正達合夥公司 Soybean event syht0h2 and compositions and methods for detection thereof
AU2011344342A1 (en) 2010-12-16 2013-07-04 Bayer Intellectual Property Gmbh 6-(2-aminophenyl)picolinates and their use as herbicides
EP2468097A1 (en) 2010-12-21 2012-06-27 Bayer CropScience AG Use of Isothiazolecarboxamides to create latent host defenses in a plant
EP2471776A1 (en) 2010-12-28 2012-07-04 Bayer CropScience AG Pyridin-2-ylpropandinitriles and their use as herbicides
EP2471363A1 (en) 2010-12-30 2012-07-04 Bayer CropScience AG Use of aryl-, heteroaryl- and benzylsulfonamide carboxylic acids, -carboxylic acid esters, -carboxylic acid amides and -carbonitriles and/or its salts for increasing stress tolerance in plants
CN103492367B (en) 2011-02-17 2015-04-01 拜耳知识产权有限责任公司 Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy
CA2828639C (en) 2011-03-01 2019-02-12 Bayer Intellectual Property Gmbh 2-acyloxypyrrolin-4-ones
EP2686309B1 (en) 2011-03-15 2016-05-11 Bayer Intellectual Property GmbH Herbicide safener compositions
JP2014516919A (en) 2011-03-18 2014-07-17 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー Substituted 4-cyano-3- (2,6-difluorophenyl) -4-phenylbutanoic acid compounds, processes for their preparation and their use as herbicides and plant growth regulators
BR112013023921A2 (en) 2011-03-18 2016-08-09 Bayer Ip Gmbh Substituted (3r, 4r) -4-cyano-3,4-diphenylbutanoates, processes for their preparation and their use as herbicides and plant growth regulators
CA2830802A1 (en) 2011-03-25 2012-10-04 Bayer Intellectual Property Gmbh Use of n-(1,2,5-oxadiazol-3-yl)benzamides for controlling unwanted plants in areas of transgenic crop plants being tolerant to hppd inhibitor herbicides
KR20140033354A (en) 2011-03-25 2014-03-18 바이엘 인텔렉쳐 프로퍼티 게엠베하 Use of n-(tetrazol-4-yl)- or n-(triazol-3-yl)arylcarboxamides or their salts for controlling unwanted plants in areas of transgenic crop plants being tolerant to hppd inhibitor herbicides
AR085568A1 (en) 2011-04-15 2013-10-09 Bayer Cropscience Ag 5- (BICYCLE [4.1.0] HEPT-3-EN-2-IL) -PENTA-2,4-DIENOS AND 5- (BICYCLE [4.1.0] HEPT-3-EN-2-IL) -PENT- 2-IN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST ABIOTIC STRESS OF PLANTS
AR085585A1 (en) 2011-04-15 2013-10-09 Bayer Cropscience Ag VINIL- AND ALQUINILCICLOHEXANOLES SUBSTITUTED AS ACTIVE PRINCIPLES AGAINST STRIPS ABIOTIQUE OF PLANTS
EP2511255A1 (en) 2011-04-15 2012-10-17 Bayer CropScience AG Substituted prop-2-in-1-ol and prop-2-en-1-ol derivatives
AR090010A1 (en) 2011-04-15 2014-10-15 Bayer Cropscience Ag 5- (CICLOHEX-2-EN-1-IL) -PENTA-2,4-DIENOS AND 5- (CICLOHEX-2-EN-1-IL) -PENT-2-EN-4-INOS REPLACED AS ACTIVE PRINCIPLES AGAINST THE ABIOTIC STRESS OF PLANTS, USES AND TREATMENT METHODS
CN103957711A (en) 2011-07-04 2014-07-30 拜耳知识产权有限责任公司 Use of substituted isoquinolinones, isoquinolindiones, isoquinolintriones and dihydroisoquinolinones or in each case salts thereof as active agents against abiotic stress in plants
JP5906314B2 (en) 2011-07-15 2016-04-20 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 2,3-Diphenyl-valeronitrile derivatives, processes for their preparation and their use as herbicides and plant growth regulators
CA2855948C (en) 2011-08-11 2020-07-28 Bayer Cropscience Ag 1,2,4-triazolyl-substituted keto-enols
EP2561759A1 (en) 2011-08-26 2013-02-27 Bayer Cropscience AG Fluoroalkyl-substituted 2-amidobenzimidazoles and their effect on plant growth
CN107897194A (en) 2011-09-16 2018-04-13 拜耳知识产权有限责任公司 5 phenyl or 5 benzyl, 2 isoxazoline, 3 formic acid esters are used for the purposes for improving plant products
MX362112B (en) 2011-09-16 2019-01-07 Bayer Ip Gmbh Use of phenylpyrazolin-3-carboxylates for improving plant yield.
BR112014006217B1 (en) 2011-09-16 2019-01-15 Bayer Intellectual Property Gmbh use of acylsulfonamides to improve plant yield, method for inducing growth regulating responses in useful plants or crop plants and composition.
AR087971A1 (en) 2011-09-23 2014-04-30 Bayer Ip Gmbh USE OF ACID DERIVATIVES 1-PHENYL-PIRAZOL-3-CARBOXILIC 4-SUBSTITUTED AS ACTIVE PRINCIPLES AGAINST PLANTS ABIOTIC STRESS
EP2773614B1 (en) 2011-10-31 2016-11-30 Bayer Intellectual Property GmbH Substituted 4.cyan-3-(phenyl-4-(pyridin-3-yl) butanoates, method for their production and their use as herbicides and plant growth regulators
EP2589293A1 (en) 2011-11-03 2013-05-08 Bayer CropScience AG Herbicide safener compounds containing N-(Tetrazol-5-yl)- and N-(Triazol-5-yl)aryl carboxylic acid amides
AR089249A1 (en) 2011-12-19 2014-08-06 Bayer Ip Gmbh 4-CIANO-3-PHENYL-4- (PIRIDIN-3-IL) SUBSTITUTED BUTANOATS, PROCEDURES FOR THEIR PREPARATION AND ITS USE AS HERBICIDES AND AS REGULATORS OF GROWTH OF PLANTS
WO2013092519A1 (en) 2011-12-19 2013-06-27 Bayer Cropscience Ag Use of anthranilic acid diamide derivatives for pest control in transgenic crops
CN104203925A (en) 2012-03-29 2014-12-10 拜耳知识产权有限责任公司 5-aminopyrimidine derivatives and use thereof for combating undesired plant growth
WO2013188291A2 (en) 2012-06-15 2013-12-19 E. I. Du Pont De Nemours And Company Methods and compositions involving als variants with native substrate preference
JP2015532650A (en) 2012-09-05 2015-11-12 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Use of substituted 2-amidobenzimidazoles, 2-amidobenzoxazoles and 2-amidobenzothiazoles or their salts as active substances against abiotic plant stress
BR112015012926A2 (en) 2012-12-05 2017-07-11 Bayer Cropscience Ag use of 1- (aryl ethinyl) -, 1- (heteroaryl ethinyl) -, 1- (heterocyclyl ethinyl) substituted and 1- (cycloalkenyl ethinyl) cyclohexanols as active agents against abiotic plant stress
EP2740356A1 (en) 2012-12-05 2014-06-11 Bayer CropScience AG Substituted (2Z)-5(1-Hydroxycyclohexyl)pent-2-en-4-inic acid derivatives
EP2740720A1 (en) 2012-12-05 2014-06-11 Bayer CropScience AG Substituted bicyclic and tricyclic pent-2-en-4-inic acid derivatives and their use for enhancing the stress tolerance in plants
AR093909A1 (en) 2012-12-12 2015-06-24 Bayer Cropscience Ag USE OF ACTIVE INGREDIENTS TO CONTROL NEMATODES IN CULTURES RESISTANT TO NEMATODES
AU2013361220A1 (en) 2012-12-21 2015-04-02 Pioneer Hi-Bred International, Inc. Compositions and methods for auxin-analog conjugation
UA116559C2 (en) 2013-02-19 2018-04-10 Байєр Кропсайєнс Акцієнгезелльшафт Use of prothioconazole to induce host defence responses
US9713332B2 (en) 2013-03-13 2017-07-25 Pioneer Hi-Bred International, Inc. Glyphosate application for weed control in Brassica
US20140289906A1 (en) 2013-03-14 2014-09-25 Pioneer Hi-Bred International, Inc. Compositions Having Dicamba Decarboxylase Activity and Methods of Use
BR112015023286A2 (en) 2013-03-14 2018-03-06 Arzeda Corp recombinant polypeptide with dicamba decarboxylase activity, polynucleotide construct, cell, method of producing a host cell comprising a heterologous polynucleotide encoding a dicamba decarboxylase activity, method for decarboxylating dicamba, a dicamba derivative or a dicamba metabolite, method for detecting a polypeptide and method for detecting the presence of a polynucleotide encoding a polypeptide having dicamba decarboxylase activity
EP3360875A1 (en) 2013-05-28 2018-08-15 Astrazeneca AB Chemical compounds
AR096517A1 (en) 2013-06-07 2016-01-13 Bayer Cropscience Ag DERIVATIVES OF 5-HIDROXI-2,3-DIFENYLPENTANONITRILE REPLACED, PROCEDURES FOR THEIR PREPARATION AND ITS USE AS HERBICIDES AND / OR REGULATORS OF GROWTH OF PLANTS
CA2927180A1 (en) 2013-10-18 2015-04-23 Pioneer Hi-Bred International, Inc. Glyphosate-n-acetyltransferase (glyat) sequences and methods of use
EP3210468A1 (en) 2016-02-26 2017-08-30 Bayer CropScience Aktiengesellschaft Solvent-free formulations of low-melting point agents
EP3238540A1 (en) 2016-04-28 2017-11-01 Bayer CropScience Aktiengesellschaft Timed-release-type granular agrochemical composition and method for manufacturing same
EP3245865A1 (en) 2016-05-17 2017-11-22 Bayer CropScience Aktiengesellschaft Method for increasing yield in brassicaceae
WO2017198449A1 (en) 2016-05-15 2017-11-23 Bayer Cropscience Nv Method for increasing yield in brassicaceae
WO2017198450A1 (en) 2016-05-15 2017-11-23 Bayer Cropscience Nv Method for increasing yield in maize
WO2017198453A1 (en) 2016-05-16 2017-11-23 Bayer Cropscience Nv Method for increasing yield in potato, tomato or alfalfa
WO2017198452A1 (en) 2016-05-16 2017-11-23 Bayer Cropscience Nv Method for increasing yield in soybean
WO2017198451A1 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in small grain cereals such as wheat and rice
WO2017198455A2 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in beta spp. plants
WO2017198454A1 (en) 2016-05-17 2017-11-23 Bayer Cropscience Nv Method for increasing yield in cotton
EP3278666A1 (en) 2016-08-04 2018-02-07 Bayer CropScience Aktiengesellschaft Aqueous capsule suspension concentrates based on 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one
BR112019002733A2 (en) 2016-08-11 2019-05-14 Bayer Cropscience Ag substituted pyrazolinyl derivatives, processes for their preparation and their use as herbicides and / or plant growth regulators
JP7149264B2 (en) 2016-08-30 2022-10-06 エフ エム シー コーポレーション Methods of reducing crop damage
EP3338551A1 (en) 2016-12-21 2018-06-27 Bayer CropScience Aktiengesellschaft Herbicide combinations
US20200095241A1 (en) 2016-12-22 2020-03-26 Bayer Cropscience Aktiengesellschaft Substituted 1,2,4-thiadiazolylpyrrolones and 1,2,4-thiadiazolylhydantoins and salts thereof and use thereof as herbicides
WO2018114596A1 (en) 2016-12-22 2018-06-28 Bayer Cropscience Aktiengesellschaft Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances
BR112019012567A2 (en) 2016-12-22 2019-11-26 Bayer Ag substituted azolylpyrrolones and azolylhydantoins and their salts and their use as herbicidal active substances
JP2020508293A (en) 2017-02-13 2020-03-19 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Substituted benzyl-4-aminopicolinic acid esters and pyrimidino-4-carboxylic acid esters, processes for preparing them, and their use as herbicides and plant growth regulators
EP3360872A1 (en) 2017-02-13 2018-08-15 Bayer CropScience Aktiengesellschaft Substituted benzyl-4-aminopicolinic acid esters and pyrimidin-4-carboxylic acid ester, process for their preparation and use as herbicides and regulators of plant growth
EP3378316A1 (en) 2017-03-24 2018-09-26 Bayer Aktiengesellschaft Herbicidal mixtures
WO2018177837A1 (en) 2017-03-30 2018-10-04 Bayer Aktiengesellschaft 4-cyclopentyl- and 4-cyclopropyl-2-oxopyrrolidine-3-carboxamide derivatives and related compounds as herbicidal plant protection agents
WO2018177836A1 (en) 2017-03-30 2018-10-04 Bayer Aktiengesellschaft N-cyclopropyl-2-oxopyrrolidine-3-carboxamide derivatives and related compounds as herbicidal plant protection agents
BR112019020877A2 (en) 2017-04-05 2020-05-12 Bayer Cropscience Aktiengesellschaft 2-AMINO-5-OXYALKYL-PYRIMIDINE DERIVATIVES AND THEIR USE TO CONTROL THE GROWTH OF UNWANTED PLANTS
BR112019023009A2 (en) 2017-05-04 2020-05-19 Bayer Cropscience Ag phytoprotective herbicide compositions containing quinazolinadione-6-carbonyl derivatives
CN106986801A (en) * 2017-05-08 2017-07-28 铜仁学院 A kind of new methoxy acrylic ester compounds and its preparation method and application
CN110799511B (en) 2017-06-13 2023-09-01 拜耳公司 Herbicidal 3-phenylisoxazoline-5-carboxamides of tetrahydro-and dihydrofurancarboxamides
BR122023020315A2 (en) 2017-06-13 2023-12-12 Bayer Aktiengesellschaft 3-PHENYLYSOXAZOLINE-5-CARBOXAMIDES
JP2020525461A (en) 2017-07-03 2020-08-27 バイエル・クロップサイエンス・アクチェンゲゼルシャフト Novel isothiazolo-based bicycles, process for their preparation, and their use as herbicides and/or plant growth regulators
BR112020000083A2 (en) 2017-07-03 2020-07-07 Bayer Cropscience Aktiengesellschaft new substituted isothiazolopyridones, processes for their preparation and use as herbicides and / or plant growth regulators
CN110891941A (en) 2017-07-18 2020-03-17 拜耳作物科学股份公司 Substituted 5- (hetero) arylpyrazolamides and their salts and their use as herbicidally active substances
CA3070010A1 (en) 2017-07-18 2019-01-24 Bayer Cropscience Aktiengesellschaft Substituted 3-heteroaryloxy-1h-pyrazoles and salts thereof and their use as herbicidal active substances
WO2019025156A1 (en) 2017-08-03 2019-02-07 Bayer Aktiengesellschaft Substituted pyrrolidinones, salts thereof and use thereof as herbicidal agents
BR112020002715A2 (en) 2017-08-09 2020-07-28 Bayer Aktiengesellschaft crystal forms of 2 - [(2,4-dichlorophenyl) methyl] -4,4-dimethyl-isoxazolidin-3-one
WO2019034602A1 (en) 2017-08-17 2019-02-21 Bayer Aktiengesellschaft Herbicidally active 3-phenyl-5-trifluoromethylisoxazoline-5-carboxamides of cyclopentylcarboxylic acids and esters
EP3473103A1 (en) 2017-10-17 2019-04-24 Bayer AG Aqueous suspension concentrates based on 2- [(2,4-dichlorophenyl) -methyl] -4,4 '-dimethyl-3-isoxazolidinone
WO2019081485A1 (en) 2017-10-26 2019-05-02 Bayer Cropscience Aktiengesellschaft Substituted pyrazoles, salts thereof and use thereof as herbicidal agents
WO2019081477A1 (en) 2017-10-26 2019-05-02 Bayer Cropscience Aktiengesellschaft Substituted pyrazoles, salts thereof and use thereof as herbicidal agents
EP3360417A1 (en) 2017-11-02 2018-08-15 Bayer CropScience Aktiengesellschaft Use of sulfonylindol as herbicide
EP3713417B1 (en) 2017-11-20 2024-01-17 Bayer Aktiengesellschaft Herbicidally active bicyclic benzamides
US20210002301A1 (en) 2017-11-29 2021-01-07 Bayer Aktiengesellschaft Novel isothiazolo-azepinone bicycles, processes for their preparation and their use as herbicides and/or plant growth regulators
CN111448194A (en) 2017-12-04 2020-07-24 拜耳作物科学股份公司 3-amino- [1,2, 4] -triazole derivatives and their use for controlling undesired vegetation
UA126935C2 (en) 2017-12-19 2023-02-22 Сінгента Кроп Протекшн Аг Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents
WO2019121547A1 (en) 2017-12-19 2019-06-27 Bayer Aktiengesellschaft Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents
EP3728237B1 (en) 2017-12-19 2022-02-09 Syngenta Crop Protection AG Substituted thiophenyluracils , their salts and use of said compounds as herbicidal agents
AU2018391579A1 (en) 2017-12-19 2020-08-06 Bayer Aktiengesellschaft Substituted N-heterocyclyl- and N-heteroaryl-tetrahydropyrimidinones and the salts thereof, and the use of same as herbicidal active substances
EP3743411B1 (en) 2018-01-25 2022-12-21 Bayer Aktiengesellschaft Herbicidal 3-phenylisoxazolin-5-carboxamides of cyclopentenyl carboxylic acid derivatives
AU2019229316A1 (en) 2018-02-28 2020-09-03 Bayer Aktiengesellschaft Method of reducing crop damage
AU2019229317A1 (en) * 2018-02-28 2020-08-27 Bayer Aktiengesellschaft Method of reducing crop damage
AU2019229318A1 (en) * 2018-02-28 2020-08-27 Bayer Aktiengesellschaft Method of reducing crop damage
EP3533329A1 (en) 2018-02-28 2019-09-04 Bayer AG Method of reducing crop damage
CA3092136A1 (en) * 2018-02-28 2019-09-06 Bayer Aktiengesellschaft Method of reducing crop damage
WO2019179928A1 (en) 2018-03-20 2019-09-26 Bayer Aktiengesellschaft Substituted succinimide-3-carboxamides, salts thereof and the use thereof as herbicidal agents
UA128091C2 (en) 2018-05-03 2024-04-03 Баєр Акціенгезельшафт Aqueous capsule suspension concentrates containing a herbicidal safener and a pesticidal active substance
WO2019219584A1 (en) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft New spiro cyclohexyl pyrrolin-2-ones and their use as herbicides
WO2019219588A1 (en) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft Specifically substituted 2-alkyl-6-alkoxyphenyl-3-pyrrolin-2-ones and their use as herbicides
EA202092643A1 (en) 2018-05-15 2021-03-22 Байер Акциенгезельшафт 2-BROMINE-6-ALCOXYPHENYL-SUBSTITUTED PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES
WO2019219585A1 (en) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft New 3-(4-alkynyl-6-alkoxy-2-chlorophenyl)-3-pyrrolin-2-ones and their use as herbicides
WO2019228788A1 (en) 2018-05-29 2019-12-05 Bayer Aktiengesellschaft 2-bromo-6-alkoxyphenyl-substituted pyrrolin-2-ones and their use as herbicides
WO2019228787A1 (en) 2018-05-29 2019-12-05 Bayer Aktiengesellschaft Specifically substituted 2-alkyl-6-alkoxyphenyl-3-pyrrolin-2-ones and their use as herbicides
US20210323950A1 (en) 2018-06-04 2021-10-21 Bayer Aktiengesellschaft Herbicidally active bicyclic benzoylpyrazoles
CA3102404A1 (en) 2018-06-05 2019-12-12 Flagship Pioneering Innovations V, Inc. Active agents and methods of their use for the treatment of metabolic disorders and nonalcoholic fatty liver disease
WO2020002090A1 (en) 2018-06-25 2020-01-02 Bayer Aktiengesellschaft Substituted thiazolylpyrrolones, salts thereof and the use thereof as herbicidal agents
WO2020016134A1 (en) 2018-07-16 2020-01-23 Bayer Aktiengesellschaft Herbicidal mixtures containing aclonifen and cinmethylin
US20210321610A1 (en) 2018-07-27 2021-10-21 Bayer Aktiengesellschaft Controlled release formulations for agrochemicals
US20210307322A1 (en) 2018-07-31 2021-10-07 Bayer Aktiengesellschaft Controlled release formulations with lignin for agrochemicals
BR112021005146A2 (en) 2018-09-19 2021-06-15 Bayer Aktiengesellschaft herbicidally active substituted phenylpyrimidine hydrazides
WO2020064260A1 (en) 2018-09-24 2020-04-02 Bayer Aktiengesellschaft Substituted 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides and salts thereof and their use as herbicidal active substances
EP3639664A1 (en) 2018-10-16 2020-04-22 Bayer AG Herbicide combinations
WO2020078874A1 (en) 2018-10-16 2020-04-23 Bayer Aktiengesellschaft Herbicide combinations
EP3639665A1 (en) 2018-10-16 2020-04-22 Bayer AG Herbicide combinations
EP3670505A1 (en) 2018-12-18 2020-06-24 Bayer AG Substituted pyridinyloxybenzenes, their salts and use of said compounds as herbicidal agents
MX2021008433A (en) 2019-01-14 2021-08-19 Bayer Ag Herbicidal substituted n-tetrazolyl aryl carboxamides.
US20220153725A1 (en) 2019-02-20 2022-05-19 Bayer Aktiengesellschaft Herbicidally active 4-(4-trifluormethyl-6-cycloropylpyrazolyl)pyrimidines
DK3937637T3 (en) 2019-03-12 2023-07-24 Bayer Ag HERBICIDELY ACTIVE 3-PHENYLISOXAZOLINE-5-CARBOXAMIDES OF S-CONTAINING CYCLOPENTENYLCARBONY ACID ESTERS
BR112021013645A2 (en) 2019-03-15 2021-09-14 Bayer Aktiengesellschaft 3- (2-HALO-6-ALKYL-4-PROPYNYLPHENYL)-3-PYRROLIN-2-ONAS SPECIALLY SUBSTITUTED AND ITS APPLICATION AS A HERBICIDE
CA3133194A1 (en) 2019-03-15 2020-09-24 Bayer Aktiengesellschaft 3-(2-brom-4-alkynyl-6-alkoxyphenyl)-substituted 5-spirocyclohexyl-3-pyrrolin-2-ones and their use as herbicides
US20220056040A1 (en) 2019-03-15 2022-02-24 Bayer Aktiengesellschaft Novel 3-(2-bromo-4-alkynyl-6-alkoxyphenyl)-3-pyrrolin-2-ones and their use as herbicides
CN113557232A (en) 2019-03-15 2021-10-26 拜耳公司 Specific substituted 3- (2-alkoxy-6-alkyl-4-propynylphenyl) -3-pyrrolin-2-ones and their use as herbicides
WO2020187626A1 (en) 2019-03-15 2020-09-24 Bayer Aktiengesellschaft Specifically substituted 3-phenyl-5-spirocyclopentyl-3-pyrrolin-2-ones and their use as herbicides
WO2020193474A1 (en) 2019-03-27 2020-10-01 Bayer Aktiengesellschaft Substituted 2-heteroarylaminobenzenes and the salts thereof and their use as herbicidal agents
US20220211040A1 (en) 2019-05-08 2022-07-07 Bayer Aktiengesellschaft High spreading ulv formulations for insecticides
BR112021020565A2 (en) 2019-06-03 2021-12-21 Bayer Ag 1-Phenyl-5-azinyl pyrazolyl-3-oxyalkyl acids and their use for controlling unwanted plant growth
WO2020245097A1 (en) 2019-06-04 2020-12-10 Bayer Aktiengesellschaft Substituted pyridinyloxypyridines and salts thereof and use thereof as herbicidal agents
EP3747868A1 (en) 2019-06-04 2020-12-09 Bayer AG Substituted phenoxypyridines, their salts and use of said compounds as herbicidal agents
EP3747867A1 (en) 2019-06-04 2020-12-09 Bayer AG Substituted pyridinyloxyanilines, their salts and use of said compounds as herbicidal agents
US20220274954A1 (en) 2019-07-22 2022-09-01 Bayer Aktiengesellschaft Substituted n-phenyl-n-aminouarcils and salts thereof and use thereof as herbicidal agents
BR112021026526A2 (en) 2019-07-22 2022-04-26 Bayer Ag Substituted N-phenyluracils, their salts and their use as herbicidal agents
WO2021028419A1 (en) 2019-08-13 2021-02-18 Bayer Aktiengesellschaft Substituted 3-(2-heteroaryloxyphenyl)isoxazolines and salts thereof and their use as herbicidal active substances
WO2021028421A1 (en) 2019-08-13 2021-02-18 Bayer Aktiengesellschaft Substituted (2-heteroaryloxyphenyl)isoxazolines and salts thereof and their use as herbicidal active substances
US20220304305A1 (en) 2019-09-11 2022-09-29 Bayer Aktiengesellschaft Highly effective formulations on the basis of 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinones and preemergence herbicides
CN114929019A (en) * 2019-11-15 2022-08-19 阿肯色大学董事会 Glufosinate additives for improved weed control
EP3679794A1 (en) 2019-11-27 2020-07-15 Bayer AG Herbicidal compositions
EP4075979A1 (en) 2019-12-19 2022-10-26 Bayer Aktiengesellschaft 1,5-diphenylpyrazolyl-3-oxyalkyl acids and 1-phenyl-5-thienylpyrazolyl-3-oxyalkyl acids and the use thereof for control of undesired plant growth
EP3845304A1 (en) 2019-12-30 2021-07-07 Bayer AG Capsule suspension concentrates based on polyisocyanates and biodegradable amine based cross-linker
BR112022012674A2 (en) 2020-01-31 2022-09-06 Bayer Ag [(1,4,5-TRISUBSTITUTED-1H-PYRAZOL-3-IL)SULPHANYL]ACETIC ACID DERIVATIVES AND SALTS THEREOF AND USE THEREOF AS ACTIVE HERBICIDES INGREDIENTS
EP4132917B1 (en) 2020-04-07 2024-01-24 Bayer Aktiengesellschaft Substituted isophtalic acid diamides
WO2021204589A1 (en) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
AU2021251361A1 (en) 2020-04-07 2022-11-03 Bayer Aktiengesellschaft Substituted isophthalic acid diamides
WO2021204669A1 (en) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Substituted isophthalic acid diamides
WO2021204666A1 (en) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Substituted isophthalic acid diamides and their use as herbicides
WO2021204884A1 (en) 2020-04-09 2021-10-14 Bayer Aktiengesellschaft 3-(4-alkenyl-phenyl)-3-pyrrolin-2-ones and their use as herbicides
WO2021209486A1 (en) 2020-04-15 2021-10-21 Bayer Aktiengesellschaft Specifically substituted pyrroline-2-ones and their use as herbicides
AU2021263052A1 (en) 2020-04-29 2022-12-08 Bayer Aktiengesellschaft 1-pyrazinylpyrazolyl-3-oxyalkyl acids and their derivatives, and their use for control of undesired plant growth
EP4157851A1 (en) 2020-05-27 2023-04-05 Bayer Aktiengesellschaft Substituted pyrroline-2-ones and their use as herbicides
KR20230029810A (en) 2020-06-26 2023-03-03 바이엘 악티엔게젤샤프트 Aqueous capsule suspension concentrate containing biodegradable ester groups
EP4172153A1 (en) 2020-06-30 2023-05-03 Bayer Aktiengesellschaft Substituted heteroaryloxypyridines, the salts thereof and their use as herbicidal agents
AU2021334085A1 (en) 2020-08-24 2023-03-23 Bayer Aktiengesellschaft Substituted N-phenyluracils and salts thereof, and use thereof as herbicidal active substances
JP2023549462A (en) 2020-10-23 2023-11-27 バイエル・アクチエンゲゼルシヤフト 1-(Pyridyl)-5-azinylpyrazole derivatives and their use for the control of undesirable plant growth
EP4026833A1 (en) 2021-01-12 2022-07-13 Bayer Aktiengesellschaft Herbicidally active 2-(het)arylmethyl pyrimidines
WO2022152728A1 (en) 2021-01-15 2022-07-21 Bayer Aktiengesellschaft Herbicidal compositions
US20240174618A1 (en) 2021-02-04 2024-05-30 Bayer Aktiengesellschaft Substituted (2-heteroaryloxyphenyl)sulfonates, salts thereof and their use as herbicidal agents
WO2022194843A1 (en) 2021-03-19 2022-09-22 Bayer Aktiengesellschaft Substituted 1,2,4-thiadiazoles, salts thereof and their use as herbicidally active substances
WO2022194842A1 (en) 2021-03-19 2022-09-22 Bayer Aktiengesellschaft Substituted 1,2,4-thiadiazoles, salts thereof and their use as herbicidally active substances
WO2022194841A1 (en) 2021-03-19 2022-09-22 Bayer Aktiengesellschaft Substituted 1,2,4-thiadiazoles, salts thereof and their use as herbicidally active substances
CA3214106A1 (en) 2021-03-22 2022-09-29 Bayer Aktiengesellschaft Substituted pyrrolidin-2-ones, salts thereof and their use as herbicidally active substances
WO2022207494A1 (en) 2021-03-30 2022-10-06 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
BR112023019788A2 (en) 2021-03-30 2023-11-07 Bayer Ag 3-(HETERO)ARYL-5-CHLORODIFLOROMETHYL-1,2,4-OXADIAZOLE AS A FUNGICIDE
AR125453A1 (en) 2021-04-27 2023-07-19 Bayer Ag SUBSTITUTED PYRIDAZINONES, SALTS OR N-OXIDES THEREOF AND THEIR USE AS HERBICIDALLY ACTIVE SUBSTANCES
WO2022253700A1 (en) 2021-06-01 2022-12-08 Bayer Aktiengesellschaft Specifically substituted pyrroline-2-ones and their use as herbicides
UY39792A (en) 2021-06-02 2023-01-31 Bayer Ag HERBICIDAL COMPOSITIONS COMPRISING ETHOFUMESATE AND A PROTECTOR, AND USES THEREOF
CA3225190A1 (en) 2021-06-25 2022-12-29 Bayer Aktiengesellschaft (1,4,5-trisubstituted-1h-pyrazole-3-yl)oxy-2-alkoxy alkyl acids and their derivatives, their salts and their use as herbicidal agents
WO2023274869A1 (en) 2021-06-29 2023-01-05 Bayer Aktiengesellschaft 3-(4-alkenyl-phenyl)-3-pyrrolino-2-ones and their use as herbicides
CA3225637A1 (en) 2021-07-02 2023-01-05 Bayer Aktiengesellschaft Herbicidal compositions containing cinmethyline and ethofumesate
AR126252A1 (en) 2021-07-08 2023-10-04 Bayer Ag SUBSTITUTED BENZOIC ACID AMIDES
CA3228106A1 (en) 2021-08-02 2023-02-09 Bayer Aktiengesellschaft Use of compositions with ethofumesate and bixlozone in wheat crops
WO2023020964A1 (en) 2021-08-17 2023-02-23 Bayer Aktiengesellschaft Substituted 1,2,4-thiadiazolyl nicotinamides, salts or n-oxides thereof and their use as herbicidally active substances
WO2023020963A1 (en) 2021-08-17 2023-02-23 Bayer Aktiengesellschaft Substituted 1,2,4-thiadiazolyl nicotinamides, salts or n-oxides thereof and their use as herbicidally active substances
WO2023020962A1 (en) 2021-08-17 2023-02-23 Bayer Aktiengesellschaft Substituted 1,2,4-thiadiazolyl nicotinamides, salts or n-oxides thereof and their use as herbicidally active substances
TW202328150A (en) 2021-09-07 2023-07-16 德商拜耳廠股份有限公司 Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
TW202328151A (en) 2021-09-07 2023-07-16 德商拜耳廠股份有限公司 Substituted 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, salts thereof and their use as herbicidally active substances
AR127618A1 (en) 2021-11-29 2024-02-14 Bayer Ag SUBSTITUTED DIHYDROPYRANOPYRIDINES, SALTS OR N-OXIDES THEREOF AND THEIR USE AS HERBICIDALLY ACTIVE SUBSTANCES
WO2023099381A1 (en) 2021-12-01 2023-06-08 Bayer Aktiengesellschaft (1,4,5-trisubstituted-1h-pyrazole-3-yl)oxy-2-alkoxythio alkyl acids and derivatives thereof, their salts and their use as herbicidal active agents
WO2023110656A1 (en) 2021-12-15 2023-06-22 Bayer Aktiengesellschaft Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis
WO2023110813A1 (en) 2021-12-15 2023-06-22 Bayer Aktiengesellschaft Use of isoxazolinecarboxamide for sprout inhibition
EP4230620A1 (en) 2022-02-22 2023-08-23 Bayer Aktiengesellschaft Substituted n-amino-n-benzoic acid uracils, their salts and use of said compounds as herbicidal agents
EP4230621A1 (en) 2022-02-22 2023-08-23 Bayer AG Substituted n-benzoic acid uracils, their salts and use of said compounds as herbicidal agents
WO2023161172A1 (en) 2022-02-22 2023-08-31 Bayer Aktiengesellschaft Substituted n-benzoic acid uracils and salts thereof, and use thereof as herbicidal active substances
EP4238973A1 (en) 2022-03-04 2023-09-06 Bayer AG Substituted 1,2,4-thiadiazolyl isonicotinamides, salts or n-oxides thereof and their use as herbicidally active substances
EP4238972A1 (en) 2022-03-04 2023-09-06 Bayer AG Substituted 1,2,4-thiadiazolyl picolinamides, salts or n-oxides thereof and their use as herbicidally active substances
WO2023186690A1 (en) 2022-03-28 2023-10-05 Bayer Aktiengesellschaft Substituted 2-aminoazines and salts thereof, and use thereof as herbicidal active substances
WO2023186691A1 (en) 2022-03-28 2023-10-05 Bayer Aktiengesellschaft Substituted 2-c-azines and salts thereof, and use thereof as herbicidal active substances
WO2023213626A1 (en) 2022-05-03 2023-11-09 Bayer Aktiengesellschaft Use of (5s)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4h-1,2,4-oxadiazine for controlling unwanted microorganisms
WO2023213670A1 (en) 2022-05-03 2023-11-09 Bayer Aktiengesellschaft Crystalline forms of (5s)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4h-1,2,4-oxadiazine
EP4273147A1 (en) 2022-05-05 2023-11-08 Bayer Aktiengesellschaft Substituted spirolactams, salts thereof and their use as herbicidally active substances
WO2023238718A1 (en) * 2022-06-10 2023-12-14 石原産業株式会社 Herbicidal composition containing difluorobutene acid amide compound
WO2024013016A1 (en) 2022-07-11 2024-01-18 Bayer Aktiengesellschaft Herbicidal compositions
WO2024013015A1 (en) 2022-07-11 2024-01-18 Bayer Aktiengesellschaft Herbicidal compositions
WO2024068520A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2024068519A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2024068518A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-heteroaryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
WO2024068517A1 (en) 2022-09-28 2024-04-04 Bayer Aktiengesellschaft 3-(hetero)aryl-5-chlorodifluoromethyl-1,2,4-oxadiazole as fungicide
EP4295688A1 (en) 2022-09-28 2023-12-27 Bayer Aktiengesellschaft Active compound combination
WO2024078906A1 (en) 2022-10-10 2024-04-18 Bayer Aktiengesellschaft Substituted n-phenyluracils and salts thereof, and use thereof as herbicidal active substances
EP4353082A1 (en) 2022-10-14 2024-04-17 Bayer Aktiengesellschaft Herbicidal compositions
WO2024078871A1 (en) 2022-10-14 2024-04-18 Bayer Aktiengesellschaft 1-pyridyl-5-phenylpyrazolyl-3-oxy- and -3-thioalkyl acids and derivatives and their use for controlling undesired plant growth
WO2024104954A1 (en) 2022-11-16 2024-05-23 Bayer Aktiengesellschaft Substituted cycloalkyloxyphenyluracils and salts thereof, and use thereof as herbicidal active substances
WO2024104952A1 (en) 2022-11-16 2024-05-23 Bayer Aktiengesellschaft Substituted cyclopropyloxyphenyluracils and salts thereof, and use thereof as herbicidal active substances
WO2024104956A1 (en) 2022-11-16 2024-05-23 Bayer Aktiengesellschaft Substituted cycloalkylsulfanylphenyluracils and their salts, and their use as herbicidal active substances
WO2024104643A1 (en) 2022-11-17 2024-05-23 Bayer Aktiengesellschaft Use of isotianil for controlling plasmodiophora brassica

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1542872A1 (en) * 1966-03-25 1970-07-02 Bayer Ag Selective herbicidal agent
US4375563A (en) * 1975-11-14 1983-03-01 Hoffmann-La Roche Inc. Fluorinated aromatic polyenes
US4321084A (en) 1977-09-23 1982-03-23 Stauffer Chemical Company Certain halogenated phenols as antidotes for thiocarbamate herbicides
US4808208A (en) * 1986-08-04 1989-02-28 Canadian Patents & Development Ltd. Phenolic safeners for glyphosate herbicides
BR9107199A (en) 1990-12-31 1994-04-05 Monsanto Co Preservation against interaction of pesticides in plantations
US5236887B1 (en) 1991-05-03 1996-04-16 Dowelanco Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-d below a ph of 5
DE4124989A1 (en) * 1991-07-27 1993-02-04 Basf Ag (BETA) -SUBSTITUTED CINNAMENT DERIVATIVES
US5739080A (en) 1994-09-15 1998-04-14 Sandoz Ltd. Safened herbicidal compositions comprising a phytotoxicity reducing phenoxy acid herbicide and a sulfonylurea, sulfonamide, or imidazolinone herbicide
DE4424791A1 (en) * 1994-07-14 1996-01-18 Basf Ag Substituted cinnamon and cinnamic hydroxamide derivatives
DE4438578A1 (en) * 1994-10-28 1996-05-02 Basf Ag Substituted phthalimido-cinnamic acid derivatives and intermediates for their preparation
DE19652961A1 (en) * 1996-12-19 1998-06-25 Hoechst Schering Agrevo Gmbh New 2-fluoroacrylic acid derivatives, new mixtures of herbicides and antidots and their use
GB9815177D0 (en) * 1998-07-13 1998-09-09 King S College London Treatment of skin disorders
DE19933897A1 (en) 1999-07-22 2001-01-25 Basf Ag Increasing the resistance of cultivated plants to chemical stress triggered by insufficiently selective or incorrect use of herbicides comprises using prohexadione or its salts, trinexapac ethyl, benzothiadiazole or probenzazole
DE10119721A1 (en) * 2001-04-21 2002-10-31 Bayer Cropscience Gmbh Herbicidal compositions containing benzoylcyclohexanediones and safeners

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005016001A1 *

Also Published As

Publication number Publication date
CN1829442B (en) 2011-05-04
DE10335725A1 (en) 2005-03-03
WO2005016001A1 (en) 2005-02-24
MXPA06001422A (en) 2006-05-15
KR20060120576A (en) 2006-11-27
EA011453B1 (en) 2009-04-28
AU2004264657A1 (en) 2005-02-24
CR8218A (en) 2007-09-14
JP2007501198A (en) 2007-01-25
RS20060038A (en) 2008-06-05
US20050049145A1 (en) 2005-03-03
UA89034C2 (en) 2009-12-25
JP4913592B2 (en) 2012-04-11
AR045202A1 (en) 2005-10-19
IL173467A0 (en) 2006-06-11
US7838463B2 (en) 2010-11-23
CA2534744A1 (en) 2005-02-24
ZA200600085B (en) 2007-01-31
CN1829442A (en) 2006-09-06
BRPI0413358A (en) 2006-10-10
AU2004264657B2 (en) 2011-04-07
EA200600325A1 (en) 2006-08-25

Similar Documents

Publication Publication Date Title
AU2004264657B2 (en) Safener based on aromatic-aliphatic carboxylic acid derivatives
AU2004264297B2 (en) Use of aromatic compounds as safeners
AU2004224813B2 (en) Use of aromatic hydroxy compounds as safeners
US20070021303A1 (en) Safening method
DE60313996T2 (en) ARYLOXYPHENOXYPROPIONATE AND SAFENER CONTAINING MEDICINES AND THEIR USE FOR INCREASING WEED PREVENTION
EP1427281B1 (en) Herbicide and safening combinations
EP2538786A2 (en) Herbicide compositions containing the hydrates of saflufenacil and glyphosates or glufosinates
EP1771071A1 (en) Herbicidal agents
DE60304862T2 (en) COMBINATIONS OF HERBIC AROMATIC CARBOXYLIC ACIDS AND SAFENER AGENTS

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20060306

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: HR

RAX Requested extension states of the european patent have changed

Extension state: HR

Payment date: 20060306

17Q First examination report despatched

Effective date: 20070129

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER CROPSCIENCE AG

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20120514