EP1653806A1 - Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques - Google Patents

Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques

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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
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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.)
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Application number
EP04763519A
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German (de)
English (en)
Inventor
Udo Bickers
Lothar Willms
Christopher Rosinger
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Bayer CropScience AG
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Bayer CropScience AG
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Publication date
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Publication of EP1653806A1 publication Critical patent/EP1653806A1/fr
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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)

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  • 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

L'invention concerne des composés de formule (I) ou des sels de ceux-ci, R<1> représentant COOH ou un dérivé de celui-ci, de préférence un groupe de formule -CN, -C(=X)-Y-R ou -C(X'R')(X''R'')-Y-R, R représentant H, un groupe hydrocarboné (subst.), un groupe hétérocyclique ou un groupe acyle, Y représentant une liaison directe ou O, S, NR<c> ou NR<c>-NR<d>R<e>, n étant un nombre entier compris entre 1 et 6 et R', R'', X, X', X'', R<a>, R<b>, R<c>, R<d>, R<e>, R<2>, R<3>, (R<4>)m étant tels que définis dans la revendication 1. Ces composés peuvent être utilisés comme agents phytosanitaires, pour des plantes cultivées ou des plantes utiles, contre les effets phytotoxiques de produits agrochimiques, de préférence comme agents phytosanitaires contre l'effet des pesticides, tels que les herbicides, sur ces plantes. Ces composés de formule (I) ou les sels de ceux-ci, R<1> représentant COOH, R<2> et R<3> représentant chacun un atome d'hydrogène, (R<4>)m représentant un groupe hydroxy (m = 1) dans n'importe quelle position ou deux groupes R<4> (m = 2) dans n'importe quelle position ou, en dernier lieu, un des groupes représentant un groupe hydroxy et l'autre groupe un groupe hydroxy ou méthoxy, et n étant égal à 1, peuvent être utilisés comme agents phytosanitaires, pour des plantes cultivées ou des plantes utiles, contre les effets phytotoxiques de produits agrochimiques autres que les glyphosates.
EP04763519A 2003-08-05 2004-07-23 Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques Withdrawn EP1653806A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10335725A DE10335725A1 (de) 2003-08-05 2003-08-05 Safener auf Basis aromatisch-aliphatischer Carbonsäuredarivate
PCT/EP2004/008382 WO2005016001A1 (fr) 2003-08-05 2004-07-23 Agents phytoprotecteurs a base de derives d'acide carboxylique aromatiques-aliphatiques

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EP1653806A1 true EP1653806A1 (fr) 2006-05-10

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AR (1) AR045202A1 (fr)
AU (1) AU2004264657B2 (fr)
BR (1) BRPI0413358A (fr)
CA (1) CA2534744A1 (fr)
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DE (1) DE10335725A1 (fr)
EA (1) EA011453B1 (fr)
IL (1) IL173467A0 (fr)
MX (1) MXPA06001422A (fr)
RS (1) RS20060038A (fr)
UA (1) UA89034C2 (fr)
WO (1) WO2005016001A1 (fr)
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JP4913592B2 (ja) 2012-04-11
WO2005016001A1 (fr) 2005-02-24
UA89034C2 (ru) 2009-12-25
JP2007501198A (ja) 2007-01-25
CN1829442B (zh) 2011-05-04
IL173467A0 (en) 2006-06-11
BRPI0413358A (pt) 2006-10-10
US20050049145A1 (en) 2005-03-03
CN1829442A (zh) 2006-09-06
MXPA06001422A (es) 2006-05-15
AU2004264657B2 (en) 2011-04-07
DE10335725A1 (de) 2005-03-03
RS20060038A (en) 2008-06-05
CR8218A (es) 2007-09-14
US7838463B2 (en) 2010-11-23
CA2534744A1 (fr) 2005-02-24
KR20060120576A (ko) 2006-11-27
EA011453B1 (ru) 2009-04-28
AR045202A1 (es) 2005-10-19
ZA200600085B (en) 2007-01-31
AU2004264657A1 (en) 2005-02-24

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