EP1653804A1 - Utilisation d'aromates hydroxy comme phytoprotecteurs - Google Patents

Utilisation d'aromates hydroxy comme phytoprotecteurs

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Publication number
EP1653804A1
EP1653804A1 EP04741232A EP04741232A EP1653804A1 EP 1653804 A1 EP1653804 A1 EP 1653804A1 EP 04741232 A EP04741232 A EP 04741232A EP 04741232 A EP04741232 A EP 04741232A EP 1653804 A1 EP1653804 A1 EP 1653804A1
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EP
European Patent Office
Prior art keywords
alkyl
carbonyl
radicals
crc
group
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
EP04741232A
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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 of EP1653804A1 publication Critical patent/EP1653804A1/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
    • 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
    • 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
    • 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
    • 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

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, acahidides, 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.
  • agrochemicals such as xenobiocides or biocides, for example herbicides, insecticides, acahidides, nematicides or fungicides
  • 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).
  • 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, for example US-A-5,846,902, US-A-5,739,080, EP-A-512737).
  • 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 their action to improve the resistance of the plants against various stress factors such as drought.
  • the invention therefore relates to the use of compounds of the formula (I) or their salts,
  • Agrochemicals preferably as safeners against the action of pesticides, such as
  • 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).
  • stereoisomers defined by their specific spatial form such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I) and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials are produced.
  • the compounds of the formula (I) can form salts by addition of a suitable inorganic or organic acid, for example HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group, such as 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.
  • salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts.
  • 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 or 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.
  • (CrC) alkyl means a shorthand notation for open-chain alkyl having one to 4 carbon atoms, ie the radicals include methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert- butyl.
  • General alkyl radicals with a larger specified range of carbon atoms e.g. B.
  • "(-C-C 6 ) alkyl” also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
  • the lower carbon skeletons for example those having 1 to 6 carbon atoms or unsaturated groups having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl;
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals;
  • Alkenyl means, for example, vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group, preferably allyl, 1-methylprop-2-en-1
  • (C 2 -C 6 ) alkynyl means, for example, ethynyl, propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-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-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl.
  • substituted cycloalkenyl the explanations for substituted cycloalkyl apply accordingly.
  • Halogen means, for example, fluorine, chlorine, bromine or iodine.
  • 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,
  • 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.
  • oxiranyl 2-oxetanyl, 3-oxetanyl or oxolanyl
  • is a heterocyclic radical having two or three heteroatoms for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyllipyrololyl, triazolyl , Oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl or morpholinyl.
  • 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 5 , aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkanoyl amino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenyl, cycloalkenyl Alkylsulfinyl, alkyl
  • 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, (CC) alkyl, preferably methyl or ethyl, (C 1 -C 4 ) haloalkyl, preferably trifluoromethyl, (C 1 -C 4 ) alkoxy, preferably methoxy or ethoxy, ( CrC) 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 diaryiamino, acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and N-heterocycles; alkyl radicals having 1 to 4 carbon atoms are preferred;
  • Aryl is preferably phenyl or substituted phenyl; the definition given below applies to acyl, preferably (-C-C 4 ) alkanoyl. The same applies to substituted hydroxylamino or hydrazino.
  • 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, (CrC) alkoxy, (CrC 4 ) haloalkyl, (C 1 -C ) Haloalkoxy and nitro is substituted, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and trichlorophenyl, 2,4-, 3rd , 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, optionally N-substituted iminocarboxylic acids or the residue of carbonic acid monoesters, N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamic acids , Phosphonic acids, phosphinic acids.
  • acyl means formyl, alkylcarbonyl such as [(CrC 4 ) alkyl] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other residues of organic acids.
  • the radicals in the alkyl or phenyl part can be further substituted, for example in the alkyl part by one or more radicals from the group halogen, alkoxy, phenyl and phenoxy; Examples of substituents in the phenyl part are the substituents mentioned generally above for substituted phenyl.
  • Acyl 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 [(C 1 -C 4 ) alkyl] carbonyl , Phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other residues of organic acid
  • the "yl position" of a radical denotes its binding site.
  • R 1 denotes a nitrile group (-CN).
  • X is a divalent radical of the formula O, S or NR a or N-NR a R b , where R a and R b are as defined below,
  • Y is a group of the formula O, S, NR C or NR c -NR d R e , where R c , R d and R e are as defined below,
  • R is hydrogen, (C 2 -C 2 ) alkyl, (C 2 -C 2 ) alkenyl, (C 2 -C 2 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 - C 6 ) Cycloalkyl- (-C-C 4 ) alkyl, phenyl, phenyl- (CrC 4 ) alkyl, heterocyclyl or heterocyclyl- (C 1 -C 4 ) alkyl, each of the latter 10 residues being unsubstituted or by one or more residues the group halogen, hydroxy, (-C-C 4 ) alkoxy, (CC 4 ) haloalkoxy, (C 2 -C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyloxy, (CC 4 ) alkylthio, (CC 4 ) al
  • X is a divalent group of the formula O, S or NR a or N-NR a R b , preferably O or NR a , where R a and R b are as defined below, Y is a group of the formula O, S, NR C or NR c -NR d R e , preferably O or NR C , where R c , R d and R e are as defined below, R is hydrogen, (d-C ⁇ Jalkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) Alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (dC 4 ) alkyl, phenyl, phenyl- (dC 4 ) alkyl, heterocyclyl or heterocyclyl- (dC 4 ) alkyl, each of which the latter 9 radicals unsubstituted or by one or
  • R 1 is a radical of the formula -CO-OR, wherein
  • 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- (CC) alkyl, Phenyl, phenyl- (CC 4 ) alkyl, heterocyclyl or heterocyclyl- (dC) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (-C-C) alkoxy, (CC 4 ) Haloalkoxy, (CC 4 ) alkylthio, (CC 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, mono (C ⁇ -C) alkylamino, di (C ⁇ -C) alkylamino, (CrC 4 ) alkanoyl, (C ⁇
  • R is (CrC) alkyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (C 1 -C 4 ) alkoxy and (CrC) 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 also 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-
  • R 1 preferably also denotes a radical of the formula
  • R and R a are as defined above, preferably
  • R a is hydrogen or, independently of one another, the radical R as defined above or preferably (CC 4 ) alkanoyl, (CC 4 ) haloalkanoyl, [(CrC) alkoxy] carbonyl, [(CrC 4 ) haloalkoxy] carbonyl, phenylcarbonyl, phenoxycarbonyl, [ Phenyl- (-C-C 4 ) alkyl] -carbonyl, [phenyl- (CrC 4 ) alkoxy] -carbonyl, aminocarbonyl, mono [(dC) alkylamino] -carbonyl, di [(CrC 4 ) alkylamino] -carbonyl, (d - C 4 ) alkylsulfinyl, (dC 4 ) alkylsulfonyl, (CC 4 ) haloalkylsulfinyl or (d-C 4 ) haloalkylsulfony
  • 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, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl (dC 4 ) alkyl , Phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl or heterocyclyl- (dC 4 ) alkyl, each of the latter 9 residues unsubstituted or by one or more residues from the group halogen, hydroxy, (dC) alkoxy, (CC 4 ) haloalkoxy, (CC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (C ⁇ -C 4 ) alkylsulfonyl, mono (C ⁇ -C 4 ) alkylamino, di (CrC 4 ) alkylamino, (Cr
  • R c is hydrogen or, independently of one another, as defined above or preferably the radical R is
  • R c is hydrogen, (dC 4 ) alkyl which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (-C-C 4 ) alkoxy and (CC 4 ) alkylthio, or (dC 4 ) alkanoyl, (CC 4 ) Haloalkanoyl, [(dC 4 ) alkoxy] carbonyl, [(dC 4 ) haloalkoxy] carbonyl, (CC 4 ) alkylsulfinyl or (CC 4 ) alkylsulfonyl or in particular hydrogen or (dC) alkyl.
  • R 1 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-methylaminocarbonyl, N-acetyl-N-methylaminocarbonyl.
  • R 2 is hydrogen, (-CC 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- (C C ⁇ 2 ) alkyl, phenyl, phenyl- (CrC ⁇ 2 ) alkyl, heterocyclyl or het, erocyclyl- (d-C ⁇ 2 ) alkyl, each of the latter 10 residues unsubstituted or by one or more Residues from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (CC 4 ) alkoxy, (CC 4 ) haloalkoxy, (C 2 - C 4 ) alkenyloxy, (C 2 -C 4 ) haloalkenyl
  • R 2 is hydrogen, (CC 12 ) alkyl, (C 2 -C 12 ) alkenyl, (C 2 -C ⁇ 2 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C 3 - C 6 ) cycloalkyl- (C 1 -C 6 ) alkyl, phenyl, phenyl- (CrC 6 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C6) alkyl, preferably in the case of the carbon-containing radicals (C ⁇ -C 8 ) alkyl, ( C 2 - C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (CC 2 ) alkyl, phenyl, phenyl- (-C
  • 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, (CC ) Alkyl, (d-C 4 ) alkoxy, (CC 4 ) haloalkyl, (dC 4 ) haloalkoxy, (CC 4 ) alkylthio and oxo.
  • R 2 is hydrogen, (dC 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl or (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, (d- C 4 ) haloalkoxy, (CC 4 ) alkylthio, (dC 4 ) alkylsulfinyl, (CC 4 ) alkylsulfonyl, (dC) alkanoyl, (CC 4 ) haloalkanoyl, [(CC) alkoxy] carbonyl and in the case of cyclic radicals also (CC 4 ) alkyl and (-C-C 4 ) haloalkyl is substituted, or, provided that Z is O or S, an acyl radical, preferably an acyl radical from
  • R 2 is hydrogen, (-CC 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C) alkynyl or (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, (dC 4 ) alkoxy, (CC 4 ) haloalkoxy, (CC 4 ) alkylthio and in the case of cyclic residues also (dC 4 ) alkyl and ( dC 4 ) haloalkyl is substituted, or, provided that at the same time is O or S, an acyl radical, preferably an acyl radical from the group consisting of the radicals (C ⁇ -d) alkanoyl, (C ⁇ -C 4 ) haloalkanoyl, [ (CC 4 ) alkoxy] carbonyl, [(dC) haloalkoxy] carbonyl,
  • the group R 2 -Z- preferably denotes a hydroxy group or an acyloxy group, e.g. B. acetyloxy or propionyloxy.
  • radicals R 3 each of the radicals R 3 independently of one another from the group consisting of halogen, SCN, CN and (d-C ⁇ s) alkyl, (C 2 -C 18 ) alkenyl, (C 2 -C 18) alkynyl, (C 3 -C 9) cycloalkyl, (C 5 - C 9) cycloalkenyl, (C 3 -C 9) cycloalkyl (dC 12) alkyl, phenyl, 12) alkyl, heterocyclyl, phenyl- (dC and heterocyclyl - (-C-C ⁇ 2 ) alkyl, each of the last 10 radicals unsubstituted or by one or more radicals from the group halogen, hydroxy, amino, cyano, nitro, thiocyanato, (CrC 4 ) alkoxy, (CrC 4 ) haloalkoxy, ( C 2 -
  • A is hydrogen or (dC 18) alkyl, (C 2 -C ⁇ ) alkenyl, (C 2 -C ⁇ 8) alkynyl, (C 3 -C 9) cycloalkyl, (C 5 - C 9) cycloalkenyl, (C 3 -C 9 ) Cycloalkyl- (CrC ⁇ 2 ) alkyl, phenyl, phenyl- (C ⁇ -C ⁇ 2 ) alkyl, heterocyclyl or heterocyclyl- (C ⁇ -C 12 ) alkyl, or preferably (d-C ⁇ 2 ) alkyl, (C 2 -C ⁇ 2 ) Alkenyl, (C 2 -C 1 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 5 -C 6 ) cycloalkenyl, (C3-C 6 ) cycloalkyl- (dC 6 ) alkyl, phenyl, phen
  • R 3 n n radicals R 3 , each of the radicals R 3 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- (CC 4 ) alkyl, phenyl, phenyl- (-C-C 4 ) alkyl, heterocyclyl and heterocyclyl- (C ⁇ -C) alkyl, and preferably thereby (CC) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkyl- (dC 2 ) alkyl, Phenyl, phenyl,
  • 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, (C ⁇ -C 4 ) alkyl, (d- C) alkoxy, (CC 4 ) haloalkyl, (dC 4 ) haloalkoxy, (CC 4 ) alkylthio and oxo.
  • group A-Z * means a hydroxyl group or an acyloxy group, e.g. B. acetyloxy or propionyloxy.
  • n denotes 0, 1, 2, 3 or 4, preferably 1 or 2, in particular 1.
  • R 1 , R 2 , R 3 and Z are as defined for formula (I).
  • each R 1 , R 2 , R 3 and Z are as defined for formula (I) and the R 3 are defined independently of one another, ie denote the same or different radicals ,
  • each of the R 3 radicals is independently selected from the group consisting of halogen and (dC) alkyl, which is unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, (dC 4 ) alkoxy, (dC) haloalkoxy, and a group of the formula -Z * -A is selected, where Z * is a group of the formula O 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 unsubstituted or by one or more radicals from the group halogen, hydroxy, (CrC 4 )
  • each of the R 3 radicals is independently selected from the group consisting of halogen, methyl, ethyl, n-propyl, i-propyl, hydroxymethyl, methoxymethyl, dimethoxymethyl, hydroxy, methoxy, ethoxy, acetoxy, propionyloxy, trifluoroacetoxy in combination with the preferred radicals and meanings for R 1 , R 2 and Z.
  • the compounds of formula (I) can be prepared by the Hydroxybenzoates or thiolbenzoates and their carboxyl derivatives are derivatized as basic compounds by conventional methods, e.g. B. acylated or etherified.
  • the invention also relates to the process 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 applied as safener, 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 to be used together with agrochemical active substances (pesticides or fertilizers), preferably pesticides for the selective control of harmful organisms, in a number of plant crops, for example in economically important crops such as cereals (wheat, barley, rye, triticale, rice, Corn, millet), sugar beet, sugar cane, rapeseed, cotton and soy.
  • agrochemical active substances pesticides or fertilizers
  • 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 glufosinates or glyphosates, or soybean crops that are 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 for use together with agrochemicals / pesticides and are then able to reduce harmful side effects of these active ingredients in crop plants or completely repeal without impairing or significantly reducing the effectiveness of these active substances against undesirable harmful organisms. Damage caused by the use of several pesticides, for example by several herbicides, insecticides or fungicides or by herbicides in combination with insecticides or fungicides, can also be substantially 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 process - i.e. immediately before application to the surface to be treated, the user mixes and dilutes the separately purchased products (crop protection agent and pesticide) - or before the application of a pesticide, or after the application of a pesticide, or for seed pretreatment, ie z. B. can be used 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.
  • suitable pesticides are herbicides, insecticides, fungicides, acahidides and nematicides which, if used alone, would result in phytotoxic damage to the crop plants or in which damage would be likely.
  • Corresponding pesticidal active substances from the groups of herbicides, insecticides, acahidides, 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 amount 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 per hectare ,
  • 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 the phytotoxic side effects on crop plants of which can be reduced by means of compounds of the formula (I), can be of very different structural classes and have very different mechanisms of action. Preference is given to commercially available herbicides, as described, for example, in the manual “The Pesticide Manual”, 13th Edition 2003, The British Crop Protection Council and the e-Pesticide Manual Version 3 (2003), or also 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
  • Herbicides whose phytotoxic side effects on crop plants can be reduced by means of compounds of the formula I are, for example, herbicides from the group of the carbamates, thiocarbamates, haloacetanilides, substituted phenoxy, naphthoxy and phenoxyphenoxycarboxylic acid derivatives and heteroaryloxyphenoxyalkane carboxylic acid derivatives, such as quinolyloxy, Quinoxalyloxy, pyridyloxy, benzoxazolyloxy and benzothiazolyloxyphenoxyalkane carboxylic acid esters, cyclo- hexandionoxime, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazoles, imidazolinones, pyrimidinyloxy-pyridine carboxylic acid derivatives, benzoic acid pyrimidyloxy Dehvate, sulfonylureas, sulphonylaminocarbon
  • 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-
  • B) herbicides from the series of sulfonylureas such as pyrimidine or triazinylaminocarbonyl- [benzene, pyridine, pyrazole, thiophene and (alkylsulfonyl) alkylamino] sulfamides.
  • 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.
  • 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.
  • alkanesulfonyl alkylamino.
  • alkoxyphenoxysulfonylureas e.g.
  • phenylaminosulfonylureas e.g. B. 1- [2- (Cyclopropylcarbonyl) phenylaminosulfonyl] -3- (4,6-dimethoxypyrimidine-2- yl) urea (cyclosulfamuron);
  • Acetochlor alachlor, butachlor, dimethachlor, dimethenamid, metazachlor, metolachlor, S-metolachlor, pethoxamide, pretilachlor, propachlor, propisochlor and thenylchlor;
  • thiocarbamates e.g. S-ethyl-N, N-dipropylthiocarbamate (EPTC), S-ethyl-N, N-diisobutylthiocarbamate (butylates);
  • Imazamethabenz-methyl imazapic, imazamox, imazapyr, imazaquin and imazethapyr;
  • 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-
  • R pyridinecarboxylic acids, e.g. B. clopyralid, fluroxypyr, picloram and triclopyr;
  • Plant growth regulators e.g. B. forchlorfenuron and thidiazuron
  • 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 compounds which can be used in combination with the crop protection compounds (I) according to the invention are preferably commercially available active compounds, for example (the compounds are generally analogous to the herbicides in the form of their "common names" in English):
  • Insecticides and active ingredients are, for example (the description is 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, thiofarboxx, methacethyx, methacofyoxametham, meth
  • Insecticides that can cause plant damage alone or together with herbicides include the following:
  • Organophosphates e.g. Terbufos (Counter ® ), Fonofos (Dyfonate ® ), Phorate
  • 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 prepared by dissolving the active ingredients in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling hydrocarbons or mixtures of the 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, alkyaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters and polyoxyethylene;
  • 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, rjiatomeenerde or flours can be obtained.
  • Wet grinding can be produced using pearl mills
  • Granules such as water-soluble granules, water-dispersible granules and
  • 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.
  • the active substance concentration in emulsifiable concentrates is the concentration of safener and / or pesticide, usually 1 to 90, in particular 5 to 80 wt .-%. Dusts usually contain 1 to 30, preferably 5 to 20% by weight of active ingredient.
  • the active substance concentration in wettable powders is generally 10 to 90% by weight.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • 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.
  • n-butyl n-Bu n-butyl
  • 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 90 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 .
  • 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 oxethylated nonylphenol as an 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 lignosulfonate, 5" sodium lauryl sulfate, 3 "polyvinyl alcohol and
  • a water-dispersible granulate is also obtained by
  • 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. 588 4-hydroxysalicylic acid (see Tab. 1)
  • Verb. 253 4-fluorosalicylic acid (see Tab. 1)
  • the pots were placed in a greenhouse under favorable growing conditions.
  • Herbicide H2 Foramsulfuron
  • Verb. 588 4-Hydroxysalicylic acid (see Tab. 1)
  • Verb. 253 4-Fluorosalicylic acid (see Tab. 1)
  • the number of crop seeds required for each amount of safener 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.
  • the seeds treated with safener and untreated seeds as controls were sown in round plastic pots with a diameter of 13 cm in a sandy loam soil and covered with an approx. 1 cm thick layer of sandy loam.
  • the herbicides in the form of liquid (for example emulsion concentrates) or dry (for example water-dispersible powders) formulations were diluted to the required concentrations with deionized water and applied to the soil surface using a spraying carriage using a water application rate of 300 liters per hectare.
  • the herbicide isoxaflutole was used as an aqueous suspension concentrate.
  • the pots were placed in a greenhouse under favorable growing conditions.
  • herbicide H1 isoxaflutole
  • Verb. 588 4-hydroxysalicylic acid (see Tab. 1)
  • Verb. 253 4-fluorosalicylic acid (see Tab. 1)
  • herbicide H1 isoxaflutole
  • Verb. 588 4-hydroxysalicylic acid (see Tab. 1)
  • Verb. 253 4-fluorosalicylic acid (see Tab. 1)
  • GLXMA Glycine max cultivar 'Lambert'
  • 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.
  • the herbicide foramsulfuron was used as a 20 percent water-dispersible powder (for results see Table 2.3.1).
  • the pots were placed in a greenhouse under favorable growing conditions.

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Abstract

L'invention concerne des composés de formule (I) ou leurs sels, où R1 signifie carboxy ou un dérivé du groupe carboxyle, de préférence un groupe de formule -CN, -C(=X)-Y-R ou -C(=X)-Het, dans laquelle X désigne O, S ou NRa ou N-NRaRb, Y représente O, S, NRc ou NRc-NRdRe, R signifie H, un groupe hydrocarbure (KW) (subst.) ou acyle, et Het désigne un hétérocycle N aliphatique, chacun des groupes Ra, Rb, Rc, Rd et Re étant défini comme R ou signifiant un groupe de formule -OR*, où R* est défini comme R, R2 représente H ou KW (subst) ou un groupe hétérocyclique ou bien encore un groupe acyle lorsque Z = O ou S, (R3 )n est n groupes R3, tel que défini à la revendication 1, Z désigne un groupe de formule O ou S(O)x, sachant que x = 0, 1 ou 2, et n est un nombre entier 0, 1, 2, 3 ou 4. Ces composés sont utilisés comme phytoprotecteurs pour les plantes utiles et de cultures pour les protéger d'effets phytotoxiques de produits chimiques agricoles, de préférence comme phytoprotecteurs contre l'effet de pesticides et d'herbicides sur ces plantes.
EP04741232A 2003-08-05 2004-07-23 Utilisation d'aromates hydroxy comme phytoprotecteurs Withdrawn EP1653804A1 (fr)

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DE10335726A DE10335726A1 (de) 2003-08-05 2003-08-05 Verwendung von Hydroxyaromaten als Safener
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Families Citing this family (292)

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Publication number Priority date Publication date Assignee Title
EP2206703A1 (fr) 2008-12-30 2010-07-14 Bayer CropScience AG Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes
RS53668B1 (en) 2005-04-13 2015-04-30 Astex Therapeutics Limited HYDROXYBENZAMIDE DERIVATIVES AND THEIR APPLICATIONS AS HSP90 INHIBITORS
JP5205063B2 (ja) * 2006-02-08 2013-06-05 クミアイ化学工業株式会社 畑地栽培除草用薬害軽減剤及びそれを用いる薬害軽減方法
US7754725B2 (en) * 2006-03-01 2010-07-13 Astex Therapeutics Ltd. Dihydroxyphenyl isoindolymethanones
US20090238763A1 (en) 2006-07-09 2009-09-24 Chongxi Yu High penetration compositions and uses thereof
WO2008007171A1 (fr) * 2006-07-09 2008-01-17 Techfields Biochem Co. Ltd Promédicaments hydrosolubles à charge positive de l'aspirine
US20090221703A1 (en) 2006-07-09 2009-09-03 Chongxi Yu High penetration composition and uses thereof
GB0620259D0 (en) 2006-10-12 2006-11-22 Astex Therapeutics Ltd Pharmaceutical compounds
WO2008044045A1 (fr) * 2006-10-12 2008-04-17 Astex Therapeutics Limited Combinaisons pharmaceutiques
WO2008044054A2 (fr) 2006-10-12 2008-04-17 Astex Therapeutics Limited Composés pharmaceutiques
US8779132B2 (en) * 2006-10-12 2014-07-15 Astex Therapeutics Limited Pharmaceutical compounds
JP5721949B2 (ja) * 2006-10-12 2015-05-20 アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ 複合薬剤
US8916552B2 (en) * 2006-10-12 2014-12-23 Astex Therapeutics Limited Pharmaceutical combinations
EP1987717A1 (fr) 2007-04-30 2008-11-05 Bayer CropScience AG Pyridinecarboxamide, agent phytoprotecteur la comportant, son procédé de fabrication et son utilisation
CN101687792B (zh) 2007-06-04 2016-03-02 于崇曦 具有快速皮肤和生物膜穿透速度的非甾体抗炎药的前药及其医药用途
DE102007035642A1 (de) * 2007-07-30 2009-02-12 Grietje Beck Substanzen zur Protektion von Zellen und Geweben gegen Schädigung durch ungünstige Bedingungen
EP2052606A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052607A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052610A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052612A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052609A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052604A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Sel du 2-lodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamide, son procédé de fabrication, et son utilisation en tant qu'herbicide et régulateurs de croissance
EP2052615A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052616A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide et de phytoprotecteurs
EP2052603A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Utilisation du 2-lodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamide et/ou ses sels pour lutter contre des végétaux indésirables dans des cultures de plantes utiles sélectionnées ou dans une zone non cultivée
EP2052611A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052613A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052614A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2052608A1 (fr) 2007-10-24 2009-04-29 Bayer CropScience AG Combinaison d'herbicide
EP2064953A1 (fr) 2007-11-29 2009-06-03 Bayer CropScience AG Combinaison d'herbicide-azole
DE102008006005A1 (de) 2008-01-25 2009-07-30 Bayer Cropscience Ag Herbizide Verbindungen auf Basis von N-Azinyl-N'-pyridylsulfonyl-harnstoffen
EP2072512A1 (fr) 2007-12-20 2009-06-24 Bayer CropScience AG Composés herbicides à base d'urées N-azinyl-N'-pyridylsulfonyl
EP2103216A1 (fr) 2008-03-19 2009-09-23 Bayer CropScience AG Sels de 3-(5,6-dihydro-1,4,2-dioxazine-3-yl)-N-[(4,6-diméthoxypyrimidine-2-yl)carbamoyl] pyridine-2-sulfonamide choisis, leur procédé de fabrication et leur utilisation en tant qu'herbicides et régulateurs de croissance des plantes
GB0806527D0 (en) 2008-04-11 2008-05-14 Astex Therapeutics Ltd Pharmaceutical compounds
EP2110019A1 (fr) 2008-04-19 2009-10-21 Bayer CropScience AG Composés herbicides à base de N-azinyl-N'-pyridylsulfonylurées
EP2112149A1 (fr) 2008-04-22 2009-10-28 Bayer CropScience Aktiengesellschaft Dérivés de 2-[(1H-pyrazol-4-ylméthyl)-sulfonyle]-oxazole, dérivés de 2-[(1H-pyrazol-4-ylméthyl)-sulfanyle]-oxazole et dérivés chiraux de 2-[(1H-pyrazol-4-ylméthyl)-sulfinyle]-oxazole, leur procédé de fabrication ainsi que leur utilisation en tant qu'herbicides et régulateurs de croissance des plantes
EP2112143A1 (fr) 2008-04-22 2009-10-28 Bayer CropScience AG Dérivés de 2-(benzylsulfinyle)-oxazole, dérivés chirales de 2-(benzylsulfinyle) et dérivés d'oxazole 2-(benzylsulfanyle), leur procédé de preparation ainsi que leur utilisation en tant qu'herbicides et régulateurs de croissances des plantes
EP2135865A1 (fr) 2008-06-17 2009-12-23 Bayer CropScience AG Acides de vinaigre substitués 1-(diazinyle)pyrazole-4-yl, leur procédé de fabrication et d'utilisation en tant qu'herbicides et régulateurs de croissance de plantes
EP2147919A1 (fr) 2008-07-24 2010-01-27 Bayer CropScience Aktiengesellschaft Amides substitués hétérocycliques, leur procédé de fabrication et leur utilisation en tant qu'herbicide
DE102008037627A1 (de) 2008-08-14 2010-02-18 Bayer Cropscience Ag Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden
JP5405236B2 (ja) * 2008-08-29 2014-02-05 全国農業協同組合連合会 除草剤組成物
US8367873B2 (en) * 2008-10-10 2013-02-05 Bayer Cropscience Ag Phenyl-substituted bicyclooctane-1,3-dione derivatives
EP2191716A1 (fr) 2008-11-29 2010-06-02 Bayer CropScience AG Combinaison d'herbicide-phytoprotecteur
EP2191720A1 (fr) 2008-11-29 2010-06-02 Bayer CropScience AG Combinaison d'herbicide-phytoprotecteur
EP2210492A1 (fr) 2008-11-29 2010-07-28 Bayer CropScience AG Combinaison d'herbicide-phytoprotecteur
EP2191719A1 (fr) 2008-11-29 2010-06-02 Bayer CropScience AG Combinaison d'herbicide-phytoprotecteur
US8846946B2 (en) 2008-12-02 2014-09-30 Bayer Cropscience Ag Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives
US8389443B2 (en) 2008-12-02 2013-03-05 Bayer Cropscience Ag Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives
CN108191846B (zh) 2008-12-04 2021-08-20 于崇曦 高穿透性组合物及其应用
EP2194052A1 (fr) 2008-12-06 2010-06-09 Bayer CropScience AG Acides de vinaigre 1-(thiazolyl) et 1-(Isothiazolyl)pyrazole-4-yl substitués, leur procédé de fabrication et d'utilisation en tant qu'herbicides et régulateurs de croissance des plantes
EP2210879A1 (fr) 2008-12-30 2010-07-28 Bayer CropScience AG Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes
EP2406216B1 (fr) 2009-03-11 2017-04-19 Bayer Intellectual Property GmbH Kétoénoles substitués par halogenalkylméthylenoxy-phényl
EP2229813A1 (fr) 2009-03-21 2010-09-22 Bayer CropScience AG Dérivés de pyrimidine-4-ylpropanedinitrile, leur procédé de fabrication et d'utilisation en tant qu'herbicides et régulateurs de croissance végétale
AR076224A1 (es) 2009-04-22 2011-05-26 Bayer Cropscience Ag Uso de propineb como repelente de aves
EP2245935A1 (fr) 2009-05-02 2010-11-03 Bayer CropScience AG Liaisons herbicides à base d'urées solides n-azinyl-n-pyridylsulfonyl
CN102439013B (zh) 2009-05-19 2015-03-18 拜尔农作物科学股份公司 螺杂环特窗酸衍生物
WO2011039276A1 (fr) 2009-10-01 2011-04-07 Bayer Cropscience Ag Oxathiazinyl-(hétéro) arylsulfonylurées, procédé et produits intermédiaires pour leur préparation et leur utilisation en tant que pesticides et régulateurs de croissance des plantes
EP2327700A1 (fr) 2009-11-21 2011-06-01 Bayer CropScience AG Dérivés de triazine et leur utilisation pour combattre la croissance indésirable de plantes
WO2011073098A1 (fr) 2009-12-15 2011-06-23 Bayer Cropscience Ag Acides 1-(hétéroaryl)-pyrazol-4-yl-acétiques, procédés de production et utilisation desdits acides comme herbicides et régulateurs de la croissance des plantes
AU2010334818B2 (en) 2009-12-23 2015-07-09 Bayer Intellectual Property Gmbh Plants tolerant to HPPD inhibitor herbicides
AR079883A1 (es) 2009-12-23 2012-02-29 Bayer Cropscience Ag Plantas tolerantes a herbicidas inhibidores de las hppd
UY33139A (es) 2009-12-23 2011-07-29 Bayer Cropscience Ag Plantas tolerantes a herbicidas inhibidores de las hppd
BR112012015125A2 (pt) 2009-12-23 2015-09-01 Bayer Ip Gmbh "plantas tolerantes aos herbicidas inibidores de hppd"
EP2516635B1 (fr) 2009-12-23 2017-11-15 Bayer Intellectual Property GmbH Plantes tolérantes à des herbicides inhibant l'hppd
CN101774922B (zh) * 2010-01-29 2012-12-26 浙江大学 2,3-二羟基苯甲酸酯类化合物及制备和应用
BR112012020084B1 (pt) * 2010-02-10 2017-12-19 Bayer Intellectual Property Gmbh A process for the preparation of pesticides and / or herbicides and / or fungi and / or fungi and / or fungicides and / or fungicides and / or fungicides and / or fungicides. METHOD FOR INCREASING THE ACTION OF PESTICIDES AND / OR HERBICIDES AND / OR FUNGICIDES COMPREHENDING SUCH COMPOUNDS
CN103068825A (zh) * 2010-02-10 2013-04-24 拜耳知识产权有限责任公司 螺杂环取代的特特拉姆酸衍生物
US20110218107A1 (en) * 2010-03-02 2011-09-08 Bayer Cropscience Ag Use of Propineb for Physiological Curative Treatment Under Zinc Deficiency
WO2011107445A1 (fr) 2010-03-04 2011-09-09 Bayer Cropscience Ag Hydrate et forme cristalline anhydre du sel de sodium du 2-iodo-n-[(4-méthoxy-6-méthyl-1,3,5-triazin-2-yl)carbamoyl]benzène sulfonamide, leur procédé de fabrication et leur utilisation en tant qu'herbicides et régulateurs de la croissance des plantes
AR080443A1 (es) 2010-03-04 2012-04-11 Bayer Cropscience Ag 2-amidobencimidazoles sustituidos con fluruoalquilo
EP2371823A1 (fr) 2010-04-01 2011-10-05 Bayer CropScience AG Phényl-sulfonylamino-(thio)carbonyltriazolinones substitués par cyclopropyle, leur préparation et leur utilisation comme herbicides et régulateurs de la croissance des plantes
BR112012025714A2 (pt) 2010-04-06 2015-09-08 Bayer Ip Gmbh uso de ácido 4-fenilbutírico e/ou sais do mesmo para aumentar a tolerância a estresse de plantas
JP6046604B2 (ja) 2010-04-09 2016-12-21 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 非生物的ストレスに対する植物の耐性を増強させるための（１−シアノシクロプロピル）フェニルホスフィン酸の誘導体、それらのエステル及び／又はそれらの塩の使用
WO2011138280A2 (fr) 2010-05-04 2011-11-10 Bayer Cropscience Ag Combinaison herbicides-phytoprotecteurs contenant des arylpyridazinones et des phytoprotecteurs
WO2011145318A1 (fr) * 2010-05-18 2011-11-24 クミアイ化学工業株式会社 Agent de réduction d'effet néfaste pour un herbicide, composition herbicide ayant un effet néfaste réduit, et procédé pour la réduction de l'effet néfaste sur les cultures
RU2013114710A (ru) 2010-09-03 2014-10-10 Байер Интеллектуэль Проперти Гмбх Замещенные конденсированные пиримидиноны и дигидропиримидиноны
US20140056866A1 (en) 2010-09-22 2014-02-27 Bayer Intellectual Property Gmbh Use of biological or chemical control agents for controlling insects and nematodes in resistant crops
EP2460406A1 (fr) 2010-12-01 2012-06-06 Bayer CropScience AG Utilisation de fluopyram pour contrôler les nématodes dans les cultures résistant aux nématodes
JP6000264B2 (ja) 2010-10-22 2016-09-28 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 新規置換ピコリン酸、その塩及び酸誘導体、並びに、除草剤としてのその使用
EP2635550B1 (fr) 2010-11-02 2016-01-27 Bayer Intellectual Property GmbH Dérivés de bicyclooctane-1,3-dione à substitution phénylique
WO2012072660A1 (fr) 2010-12-01 2012-06-07 Bayer Cropscience Ag Utilisation de fluopyram pour la lutte contre les nématodes dans des plantes cultivées et pour l'augmentation du rendement
RU2013132601A (ru) 2010-12-16 2015-01-27 Байер Интеллектуэль Проперти Гмбх 6-(2-аминофенил)пиколинаты и их применение в качестве гербицидов
EP2468097A1 (fr) 2010-12-21 2012-06-27 Bayer CropScience AG Utilisation d'isothiazolecarboxamides pour créer des défenses latentes de l'hôte dans une plante
EP2471776A1 (fr) 2010-12-28 2012-07-04 Bayer CropScience AG Pyridine-2-ylpropandinitriles et leur utilisation comme herbicides
EP2471363A1 (fr) 2010-12-30 2012-07-04 Bayer CropScience AG Utilisation d'acides aryl-, hétéroaryl- et benzylsulfonaminés, d'esters d'acide aminé, d'amides d'acide aminé et carbonitrile ou leurs sels pour l'augmentation de la tolérance au stress dans des plantes
CN103649049B (zh) 2011-02-17 2016-06-29 拜耳知识产权有限责任公司 用于治疗的被取代的3-(联苯-3-基)-8, 8-二氟-羟基-1-氮杂螺[4.5]癸-3-烯-2-酮和被卤素取代的螺环酮烯醇
ES2550391T3 (es) 2011-03-01 2015-11-06 Bayer Intellectual Property Gmbh 2-Aciloxi-pirrolin-4-onas
EA023797B1 (ru) 2011-03-15 2016-07-29 Байер Интеллектуэль Проперти Гмбх Композиции, состоящие из гербицида и защитного вещества
WO2012126764A1 (fr) 2011-03-18 2012-09-27 Bayer Cropscience Ag 4-cyan-3-(2,6-difluorophényl)-4-phénylbutanoates substitués, procédé de préparation desdits composés et leur utilisation en tant qu'herbicides et régulateurs de la croissance des plantes
CN103476251A (zh) 2011-03-18 2013-12-25 拜耳知识产权有限责任公司 取代的(3r,4r)-4-氰基-3,4-二苯基丁酸酯，其制法和作为除草剂和植物生长调节剂的用途
AU2012234448A1 (en) 2011-03-25 2013-10-17 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
PL2688406T3 (pl) 2011-03-25 2015-10-30 Bayer Ip Gmbh Zastosowanie N-(tetrazol-4-ilo)- lub N-(triazol-3-ilo)arylokarboksamidów lub ich soli do zwalczania niepożądanych roślin w obszarach transgenicznych roślin uprawnych tolerancyjnych na środki chwastobójcze będące inhibitorem HPPD
AR090010A1 (es) 2011-04-15 2014-10-15 Bayer Cropscience Ag 5-(ciclohex-2-en-1-il)-penta-2,4-dienos y 5-(ciclohex-2-en-1-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas, usos y metodos de tratamiento
AR085585A1 (es) 2011-04-15 2013-10-09 Bayer Cropscience Ag Vinil- y alquinilciclohexanoles sustituidos como principios activos contra estres abiotico de plantas
AR085568A1 (es) 2011-04-15 2013-10-09 Bayer Cropscience Ag 5-(biciclo[4.1.0]hept-3-en-2-il)-penta-2,4-dienos y 5-(biciclo[4.1.0]hept-3-en-2-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas
EP2511255A1 (fr) 2011-04-15 2012-10-17 Bayer CropScience AG Dérivés de prop-2-yn-1-ol et prop-2-en-1-ol substitués
JP2014520776A (ja) 2011-07-04 2014-08-25 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 植物における非生物的ストレスに対する活性薬剤としての置換されているイソキノリノン類、イソキノリンジオン類、イソキノリントリオン類およびジヒドロイソキノリノン類または各場合でのそれらの塩の使用
CN103748075B (zh) 2011-07-15 2016-09-07 拜耳知识产权有限责任公司 2,3-二苯基戊腈衍生物、其制备方法及其作为除草剂和植物生长调节剂的用途
AU2012293611B2 (en) 2011-08-11 2017-02-09 Bayer Cropscience Ag 1,2,4-triazolyl-substituted keto-enols
EP2561759A1 (fr) 2011-08-26 2013-02-27 Bayer Cropscience AG 2-amidobenzimidazoles fluoroalkyl substitués et leur effet sur la croissance des plantes
CN108552186A (zh) 2011-09-16 2018-09-21 拜耳知识产权有限责任公司 苯基吡唑啉-3-甲酸酯类用于提高植物产量的用途
WO2013037956A1 (fr) 2011-09-16 2013-03-21 Bayer Intellectual Property Gmbh Utilisation de 5-phényl- ou de 5-benzyl-2 isoxazoline-3 carboxylates pour améliorer le rendement de végétaux
UA115971C2 (uk) 2011-09-16 2018-01-25 Байєр Інтеллектуал Проперті Гмбх Застосування ацилсульфонамідів для покращення врожайності рослин
CN103929964A (zh) 2011-09-23 2014-07-16 拜耳知识产权有限责任公司 4-取代的1-苯基吡唑-3-甲酸衍生物作为对抗非生物植物胁迫的活性物质的用途
KR20140084204A (ko) 2011-10-31 2014-07-04 바이엘 인텔렉쳐 프로퍼티 게엠베하 치환된 4-시아노-3-페닐-4-(피리딘-3-일)부타노에이트, 이의 제조 방법 및 제초제 및 식물 생장 조절제로서의 이의 용도
EP2589293A1 (fr) 2011-11-03 2013-05-08 Bayer CropScience AG Compositions herbicides phytoprotectrices comprenant des amides d'acide carbonique de N-(tétrazol-5-yl) et N-(triazol-5-yl)aryle
AR089249A1 (es) 2011-12-19 2014-08-06 Bayer Ip Gmbh 4-ciano-3-fenil-4-(piridin-3-il)butanoatos sustituidos, procedimientos para su preparacion y su uso como herbicidas y como reguladores del crecimiento de plantas
WO2013092519A1 (fr) 2011-12-19 2013-06-27 Bayer Cropscience Ag Utilisation de dérivés de diamide d'acide anthranilique pour lutter contre les organismes nuisibles dans des cultures transgéniques
EP4356912A2 (fr) 2012-01-18 2024-04-24 Techfields Pharma Co., Ltd. Compositions de promédicament à pénétration élevée et composition pharmaceutique de celles-ci pour le traitement d'états pulmonaires
EP2831050B1 (fr) 2012-03-29 2016-03-23 Bayer Intellectual Property GmbH Dérivés de 5-amino-pyrimidine et leur utilisation pour lutter contre la croissance indésirable de plantes
EP2892345A1 (fr) 2012-09-05 2015-07-15 Bayer CropScience AG Utilisation de 2-amidobenzimidazoles, de 2-amidobenzoxazoles et de 2-amidobenzothiazoles substitués ou de leurs sels comme principes actifs contre le stress abiotique des plantes
BR112015012926A2 (pt) 2012-12-05 2017-07-11 Bayer Cropscience Ag uso de 1-(aril etinil)-, 1-(heteroaril etinil)-, 1-(heterociclil etinil)- substituído e 1-(cicloalquenil etinil)-ciclohexanóis como agentes ativos contra o estresse abiótico da planta
EP2740356A1 (fr) 2012-12-05 2014-06-11 Bayer CropScience AG Dérivés d'acides (2Z)-5(1-hydroxycyclohexyl)pent-2-en-4-ines substitués
EP2740720A1 (fr) 2012-12-05 2014-06-11 Bayer CropScience AG Dérivés d'acides pent-2-en-4-ines bicycliques et tricycliques substitués et leur utilisation pour augmenter la tolérance au stress chez les plantes
WO2014090765A1 (fr) 2012-12-12 2014-06-19 Bayer Cropscience Ag Utilisation de 1-[2-fluoro-4-méthyle-5-(2,2,2- trifluoroéthylsulfinyl)phényl]-5-amino-3-trifluorométhyl)-1 h-1,2,4 tfia zole à des fins de régulation des nématodes dans les cultures résistantes aux nématodes
WO2014128069A1 (fr) 2013-02-19 2014-08-28 Bayer Cropscience Ag Utilisation du prothioconazole pour induire une réponse de défense de l'hôte
JP6278186B2 (ja) * 2013-03-29 2018-02-14 日産化学工業株式会社 除草剤用薬害軽減剤及び薬害が軽減された除草剤組成物
EP2796042A1 (fr) * 2013-04-23 2014-10-29 Albert-Ludwigs-Universität Freiburg Composés favorisant la croissance des plantes
AR096517A1 (es) 2013-06-07 2016-01-13 Bayer Cropscience Ag Derivados de 5-hidroxi-2,3-difenilpentanonitrilo sustituido, procedimientos para su preparación y su uso como herbicidas y/o reguladores del crecimiento de las plantas
FR3012069B1 (fr) * 2013-10-22 2015-10-23 Saint Gobain Vitrage pour systeme de visualisation
ES2757074T3 (es) 2014-06-04 2020-04-28 Monsanto Technology Llc Compuestos de ácido 3,6-diclorosalicílico y procedimientos sintéticos relacionados
JP6289438B2 (ja) * 2015-12-03 2018-03-07 テックフィールズ バイオケム カンパニー リミテッド アスピリンの正荷電水溶性プロドラッグ
CN105523955B (zh) * 2015-12-14 2018-08-17 北京嘉林药业股份有限公司 化合物及其在制备药物中的用途
CN105532657B (zh) * 2015-12-28 2018-06-19 东北农业大学 一种用于单子叶作物的除草组合物及其用途
EP3210468A1 (fr) 2016-02-26 2017-08-30 Bayer CropScience Aktiengesellschaft Compositions sans solvant pour agents actifs a bas point de fusion
EP3238540A1 (fr) 2016-04-28 2017-11-01 Bayer CropScience Aktiengesellschaft Compositions agrochimiques à libération contrôlée granulaire et son procédé de préparation
WO2017198450A1 (fr) 2016-05-15 2017-11-23 Bayer Cropscience Nv Procédé pour accroître le rendement du maïs
EP3245865A1 (fr) 2016-05-17 2017-11-22 Bayer CropScience Aktiengesellschaft Procédé pour augmenter le rendement dans des brassicacées
WO2017198449A1 (fr) 2016-05-15 2017-11-23 Bayer Cropscience Nv Procédé pour accroître le rendement chez les brassicaceae
WO2017198452A1 (fr) 2016-05-16 2017-11-23 Bayer Cropscience Nv Procédé pour accroître le rendement du soja
WO2017198453A1 (fr) 2016-05-16 2017-11-23 Bayer Cropscience Nv Procédé d'augmentation du rendement dans la pomme de terre, la tomate ou la luzerne
WO2017198455A2 (fr) 2016-05-17 2017-11-23 Bayer Cropscience Nv Procédé pour accroître le rendement de plantes bêta spp.
WO2017198454A1 (fr) 2016-05-17 2017-11-23 Bayer Cropscience Nv Procédé pour accroître le rendement du coton
WO2017198451A1 (fr) 2016-05-17 2017-11-23 Bayer Cropscience Nv Procédé pour augmenter le rendement dans des céréales à grains fins telles que le blé et le riz
EP3495415B1 (fr) * 2016-08-04 2021-01-20 Bridgestone Corporation Composition de caoutchouc, pneu, additif et composé hydrazide
EP3278666A1 (fr) 2016-08-04 2018-02-07 Bayer CropScience Aktiengesellschaft Concentrés de suspension en capsule à base de 2-(2,4-dichlorobenzyl)-4,4-diméthyl-1,2-oxazolidin-3-one
BR112019002733A2 (pt) 2016-08-11 2019-05-14 Bayer Cropscience Ag derivados de pirazolinil substituídos, processos para sua preparação e seu uso como herbicidas e/ou reguladores de crescimento da planta
SI3506747T1 (sl) 2016-08-30 2022-05-31 Bayer Cropscience Aktiengesellschaft Postopek zmanjšanja škode na pridelku
EP3338551A1 (fr) 2016-12-21 2018-06-27 Bayer CropScience Aktiengesellschaft Combinaisons herbicides
MX2019007374A (es) 2016-12-22 2019-09-18 Bayer Cropscience Ag Heteroarilpirrolonas sustituidas y sus sales y su uso como ingredientes activos herbicidas.
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
BR112019012567A2 (pt) 2016-12-22 2019-11-26 Bayer Ag azolilpirrolonas e azolil-hidantoínas substituídas e sais das mesmas e uso das mesmas como substâncias ativas herbicidas
EP3360872A1 (fr) 2017-02-13 2018-08-15 Bayer CropScience Aktiengesellschaft Ester d'acide de benzyl-4-aminopicolinic et d'acide carboxylique de pyrimidin, procédé pour leur preparation et leur usage comme herbicides et regulateurs de pousse des plants
EA201991887A1 (ru) 2017-02-13 2020-02-20 Байер Кропсайенс Акциенгезельшафт Замещенные эфиры бензил-4-аминопиколиновой кислоты и эфиры пиримидин-4-карбоновой кислоты, способы их получения, а также их применение в качестве гербицидов и регуляторов роста
JP6588485B2 (ja) * 2017-02-21 2019-10-09 テックフィールズ バイオケム カンパニー リミテッド アスピリンの正荷電水溶性プロドラッグ
EP3378316A1 (fr) 2017-03-24 2018-09-26 Bayer Aktiengesellschaft Mélanges herbicides
WO2018177836A1 (fr) 2017-03-30 2018-10-04 Bayer Aktiengesellschaft Dérivés de n-cyclopropyl-2-oxopyrrolidin-3-carboxamide et composés apparentés en tant qu'agents de phytoprotection herbicides
WO2018177837A1 (fr) 2017-03-30 2018-10-04 Bayer Aktiengesellschaft Dérivés de 4-cyclopentyl-2-oxopyrrolidin-3-carboxamide et de 4-cyclopropyl-2-oxopyrrolidin-3-carboxamide et composés apparentés utilisés comme produits phytosanitaires herbicides
WO2018184978A1 (fr) 2017-04-05 2018-10-11 Bayer Cropscience Aktiengesellschaft Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices
JP2020518625A (ja) 2017-05-04 2020-06-25 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 キナゾリンジオン−６−カルボニル誘導体を含有する除草剤毒性緩和剤組成物
HRP20211611T1 (hr) 2017-06-13 2022-02-04 Bayer Aktiengesellschaft Herbicidni 3-fenilizoksazolin-5-karboksamidi tetrahidro i dihidrofuran karboksilnih kiselina i estera
JP7082425B2 (ja) 2017-06-13 2022-06-08 バイエル・アクチエンゲゼルシヤフト 除草活性を示すテトラヒドロ及びジヒドロフランカルボキサミドの３－フェニルイソオキサゾリン－５－カルボキサミド類
BR112020000085A2 (pt) 2017-07-03 2020-07-07 Bayer Cropscience Aktiengesellschaft novos biciclos baseados em isotiazol, processos para sua preparação e seu uso como herbicidas e/ou reguladores de crescimento da planta.
CN111031799A (zh) 2017-07-03 2020-04-17 拜耳作物科学股份公司 新的取代的异噻唑并吡啶酮、其制备方法及其用作除草剂和/或植物生长调节剂的用途
US20200181117A1 (en) 2017-07-18 2020-06-11 Bayer Cropscience Aktiengesellschaft Substituted 3-heteroaryloxy-1h-pyrazoles and salts thereof and their use as herbicidal active substances
US20200172491A1 (en) 2017-07-18 2020-06-04 Bayer Cropscience Aktiengesellschaft Substituted 5-(het-)arylpyrazolamides and salts thereof and their use as herbicidal active substances
WO2019025156A1 (fr) 2017-08-03 2019-02-07 Bayer Aktiengesellschaft Pyrrolidinones substituées, leurs sels et leur utilisation comme agents herbicides
CN111051290A (zh) 2017-08-09 2020-04-21 拜耳公司 2-[(2,4-二氯苯基)甲基]-4,4-二甲基-异噁唑烷-3-酮的晶形
WO2019034602A1 (fr) 2017-08-17 2019-02-21 Bayer Aktiengesellschaft 3-phényl-5-trifluorométhylisoxazoline-5-carboxamides d'acides carboxyliques et d'esters de cyclopentyle efficaces en tant qu'herbicides
EP3473103A1 (fr) 2017-10-17 2019-04-24 Bayer AG Concentré en suspension aqueux à base de 2-[(2,4-dichlorphényl)-méthyl]-4,4'-diméthyl-3-isoxazolidinone
WO2019081477A1 (fr) 2017-10-26 2019-05-02 Bayer Cropscience Aktiengesellschaft Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides
WO2019081485A1 (fr) 2017-10-26 2019-05-02 Bayer Cropscience Aktiengesellschaft Pyrazoles substitués, leurs sels et leur utilisation comme agents herbicides
EP3360417A1 (fr) 2017-11-02 2018-08-15 Bayer CropScience Aktiengesellschaft Utilisation de sulfonylindole en tant que herbicide
WO2019096884A1 (fr) 2017-11-20 2019-05-23 Bayer Aktiengesellschaft Benzamides bicycliques à action herbicide
CN111433214A (zh) 2017-11-29 2020-07-17 拜耳公司 新的异噻唑-氮杂*酮双环、其制备方法及其作为除草剂和/或植物生长调节剂的用途
CN111448194A (zh) 2017-12-04 2020-07-24 拜耳作物科学股份公司 3-氨基-[1，2，4]-三唑衍生物及其用于防治不希望的植物生长的用途
WO2019121547A1 (fr) 2017-12-19 2019-06-27 Bayer Aktiengesellschaft Thiophényluraciles substitués, leurs sels et leur utilisation comme agents herbicides
ES2911000T3 (es) 2017-12-19 2022-05-17 Syngenta Crop Protection Ag Tiofeniluracilos sustituidos, sales de los mismos y el uso de los mismos como agentes herbicidas
EP3728237B1 (fr) 2017-12-19 2022-02-09 Syngenta Crop Protection AG Thiophényl-uraciles substitués ainsi que leurs sels et leur utilisation en tant qu'agents herbicides
BR112020012166A2 (pt) 2017-12-19 2020-11-24 Bayer Aktiengesellschaft n-heterociclil- e n-heteroaril-tetra-hidropirimidinonas substituídas e os sais das mesmas, e o uso das mesmas como substâncias ativas herbicidas
JP2018058899A (ja) * 2018-01-04 2018-04-12 テックフィールズ バイオケム カンパニー リミテッド アスピリンの正荷電水溶性プロドラッグ
WO2019145245A1 (fr) 2018-01-25 2019-08-01 Bayer Aktiengesellschaft 3-phényl-isoxazoline-5-carboxamides de dérivés d'acide cyclopentényl-carboxylique à action herbicide
CN111770684A (zh) * 2018-02-28 2020-10-13 拜耳公司 减少作物损害的方法
EA202092031A1 (ru) 2018-02-28 2021-02-10 Байер Акциенгезельшафт Способ уменьшения повреждений, ведущих к снижению урожая
EP3758484A1 (fr) * 2018-02-28 2021-01-06 Bayer Aktiengesellschaft Procédé de réduction des dommages causés aux cultures
EP3533329A1 (fr) 2018-02-28 2019-09-04 Bayer AG Procédé de réduction de dommages causés aux récoltes
AU2019229317A1 (en) 2018-02-28 2020-08-27 Bayer Aktiengesellschaft Method of reducing crop damage
WO2019179928A1 (fr) 2018-03-20 2019-09-26 Bayer Aktiengesellschaft Succinimide-3-carboxamides substitués, leurs sels et leur utilisation comme agents herbicides
EP3787407A1 (fr) 2018-05-03 2021-03-10 Bayer Aktiengesellschaft Suspensions de capsules concentrées aqueuses renfermant un phytoprotecteur et une substance active pesticide
AR115088A1 (es) 2018-05-15 2020-11-25 Bayer Ag Espirociclohexilpirrolin-2-onas y su uso como herbicidas
WO2019219585A1 (fr) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft Nouvelles 3-(4-alcinyl-6-alcoxy-2-chlorophényl)-3-pyrrolin-2-ones et leur utilisation comme herbicides
CA3100089A1 (fr) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft Pyrrolin-2-ones a substitution 2-bromo-6-alcoxyphenyle et leur utilisation comme herbicides
WO2019219588A1 (fr) 2018-05-15 2019-11-21 Bayer Aktiengesellschaft Nouvelles 2-alkyl-6-alcoxyphényl-3-pyrroliin-2-ones à substitution spéciale et leur utilisation comme herbicides
WO2019228788A1 (fr) 2018-05-29 2019-12-05 Bayer Aktiengesellschaft Pyrorroline-2-ones à substitution 2-bromo-6-alcoxyphényle et leur utilisation comme herbicides
WO2019228787A1 (fr) 2018-05-29 2019-12-05 Bayer Aktiengesellschaft 2-alkyle-6-alcoxyphényle-pyrroline-2-ones à substitution spéciale et leur utilisation comme herbicides
EP3802521A1 (fr) 2018-06-04 2021-04-14 Bayer Aktiengesellschaft Benzoylpyrazoles bicycliques utilisés comme herbicide
WO2020002090A1 (fr) 2018-06-25 2020-01-02 Bayer Aktiengesellschaft Thiazolylpyrrolones substituées, leurs sels et leur utilisation comme agents herbicides
BR112021000056A2 (pt) 2018-07-16 2021-04-06 Bayer Aktiengesellschaft Misturas herbicidas contendo aclonifeno e cinmetilina
EP3829303A1 (fr) 2018-07-27 2021-06-09 Bayer Aktiengesellschaft Formulations à libération contrôlée pour produits agrochimiques
WO2020025650A1 (fr) 2018-07-31 2020-02-06 Bayer Aktiengesellschaft Formulations à libération contrôlée contenant de la lignine pour produits agrochimiques
US20220033363A1 (en) 2018-09-19 2022-02-03 Bayer Aktiengesellschaft Herbicidally active substituted phenylpyrimidine hydrazides
WO2020064260A1 (fr) 2018-09-24 2020-04-02 Bayer Aktiengesellschaft 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides substitués et leurs sels et leur utilisation comme agents herbicides
EP3639665A1 (fr) 2018-10-16 2020-04-22 Bayer AG Combinaisons d'herbicides
EP3639664A1 (fr) 2018-10-16 2020-04-22 Bayer AG Combinaisons d'herbicides
WO2020078874A1 (fr) 2018-10-16 2020-04-23 Bayer Aktiengesellschaft Combinaisons d'herbicides
EP3670505A1 (fr) 2018-12-18 2020-06-24 Bayer AG Pyridinyloxy-benzènes substituées ainsi que leurs sels et leur utilisation en tant que substances actives herbicides
MX2021008433A (es) 2019-01-14 2021-08-19 Bayer Ag Herbicidas sustituidos n-tetrazolil arilcarboxamidas.
EP3927695A1 (fr) 2019-02-20 2021-12-29 Bayer Aktiengesellschaft 4-(4-trifluorométhyl-6-cycloropylpyrazolyl)pyrimidines à action herbicide
AU2020238493A1 (en) 2019-03-12 2021-10-07 Bayer Aktiengesellschaft Herbicidally active 3-phenylisoxazoline-5-carboxamides of s-containing cyclopentenyl carboxylic acid esters
BR112021013645A2 (pt) 2019-03-15 2021-09-14 Bayer Aktiengesellschaft 3- (2-halo-6-alquil-4-propinilfenil) -3-pirrolin-2-onas especialmente substituído e sua aplicação como herbicida
EA202192471A1 (ru) 2019-03-15 2022-02-03 Байер Акциенгезельшафт Специфически замещенные 3-фенил-5-спироциклопентил-3-пирролин-2-оны и их применение в качестве гербицидов
CA3133187A1 (fr) 2019-03-15 2020-09-24 Bayer Aktiengesellschaft Nouvelles 3-(2-brome-4-alkinyl-6-alkoxyphenyl)-3-pyrroline-2-ones et leur utilisation comme herbicides
CN113544119A (zh) 2019-03-15 2021-10-22 拜耳公司 3-(2-溴-4-炔基-6-烷氧基苯基)-取代的5-螺环己基-3-吡咯啉-2-酮及其作为除草剂的用途
BR112021011965A2 (pt) 2019-03-15 2021-09-21 Bayer Aktiengesellschaft 3-(2-alcoxi-6-alquil-4-propinilfenil)-3-pirrolin-2-ona especialmente substituído e sua aplicação como herbicida
WO2020193474A1 (fr) 2019-03-27 2020-10-01 Bayer Aktiengesellschaft 2-hétéro-arylaminobenzènes substitués, leurs sels et leur utilisation comme principes actifs herbicides
EP3965570A1 (fr) 2019-05-08 2022-03-16 Bayer Aktiengesellschaft Formulations d'ulv à étalement élevé pour herbicides
CA3142286A1 (fr) 2019-06-03 2020-12-10 Bayer Aktiengesellschaft Acides 1-phenyl-5-azinylpyrazolyl-3-oxyalkyliques et leur utilisation pour lutter contre la croissance de plantes adventices
WO2020245097A1 (fr) 2019-06-04 2020-12-10 Bayer Aktiengesellschaft Pyridinyloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides
EP3747868A1 (fr) 2019-06-04 2020-12-09 Bayer AG Phénoxypyridines substituées ainsi que leurs sels et leur utilisation en tant qu'agents herbicides
EP3747867A1 (fr) 2019-06-04 2020-12-09 Bayer AG Pyridinyloxyanilines substituées ainsi que leurs sels et leur utilisation en tant qu'agents herbicides
AU2020318682A1 (en) 2019-07-22 2022-03-03 Bayer Aktiengesellschaft Substituted N-phenyl-N-aminouarcils and salts thereof and use thereof as herbicidal agents
JP2022542068A (ja) 2019-07-22 2022-09-29 バイエル、アクチエンゲゼルシャフト 置換ｎ－フェニルウラシル、その塩および除草剤としてのこれらの使用
WO2021028421A1 (fr) 2019-08-13 2021-02-18 Bayer Aktiengesellschaft (2-hétéroaryloxyphényle) isoxazolines substituées et leurs sels et leur utilisation en tant que substances actives herbicides
WO2021028419A1 (fr) 2019-08-13 2021-02-18 Bayer Aktiengesellschaft 3-(2-hétéroaryloxyphényle)isoxazolines substituées, leurs sels et leur utilisation en tant que substances actives herbicides
BR112022004347A8 (pt) 2019-09-11 2022-10-18 Bayer Ag Formulações altamente eficazes à base de 2-[(2,4-diclorofenil)-metil]-4,4'-dimetil-3-isoxazolidinona e herbicidas de pré-emergência
KR20220106152A (ko) 2019-11-26 2022-07-28 바이엘 악티엔게젤샤프트 [(1,5-디페닐-1h-1,2,4-트리아졸-3-일)옥시]아세트산 유도체 및 그의 염, 이를 포함하는 작물 보호 조성물, 그의 생산 방법 및 완화제로서의 그의 용도
EP3679794A1 (fr) 2019-11-27 2020-07-15 Bayer AG Compositions herbicides
EP4075979A1 (fr) 2019-12-19 2022-10-26 Bayer Aktiengesellschaft Acides 1,5-diphénylpyrazolyl-3-oxyalkyle et acides 1-phényl-5-thiénylpyrazolyl-3-oxyalkyle et leur utilisation pour lutter contre la croissance de plantes adventices
EP3845304A1 (fr) 2019-12-30 2021-07-07 Bayer AG Concentrés de suspension en capsule à base de polyisocyanates et agent de réticulation biodégradable à base d'amine
EP4097087B1 (fr) 2020-01-31 2024-07-31 Bayer Aktiengesellschaft Dérivés d'acide [(1,4,5-trisubstitué-1h-pyrazol-3-yl)sulfanyl]acétique et leurs sels et leur utilisation en tant que principes actifs herbicides
CN115768752A (zh) 2020-04-07 2023-03-07 拜耳公司 取代的间苯二酸二酰胺
AU2021251341A1 (en) 2020-04-07 2022-11-03 Bayer Aktiengesellschaft Substituted thiazolopyridines, salts thereof and their use as herbicidally active substances
ES2976966T3 (es) 2020-04-07 2024-08-13 Bayer Ag Diamidas de ácido isoftálico sustituidas y su uso como herbicidas
WO2021204669A1 (fr) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Diamides d'acide isophtalique substitués
US20230150953A1 (en) 2020-04-07 2023-05-18 Bayer Aktiengesellschaft Substituted isophthalic acid diamides
WO2021204884A1 (fr) 2020-04-09 2021-10-14 Bayer Aktiengesellschaft 3-(4-alcényl-phényl)-3-pyrrolin-2-ones et leur utilisation comme herbicides
WO2021209486A1 (fr) 2020-04-15 2021-10-21 Bayer Aktiengesellschaft Pyrroline-2-ones à substitution spécifique et leur utilisation en tant qu'herbicides
EP4143181A1 (fr) 2020-04-29 2023-03-08 Bayer Aktiengesellschaft Acides 1-pyrazinylpyrazolyl-3-oxyalkyle et leurs dérivés, et leur utilisation pour lutter contre la croissance de plantes indésirables
KR20230015975A (ko) 2020-05-27 2023-01-31 바이엘 악티엔게젤샤프트 치환된 피롤린-2-온 및 제초제로서의 그의 용도
AU2021298129A1 (en) 2020-06-26 2023-02-02 Bayer Aktiengesellschaft Aqueous capsule suspension concentrates comprising biodegradable ester groups
CN115996919A (zh) 2020-06-30 2023-04-21 拜耳公司 取代的杂芳基氧基吡啶、其盐及它们作为除草剂的用途
AU2021334085A1 (en) 2020-08-24 2023-03-23 Bayer Aktiengesellschaft Substituted N-phenyluracils and salts thereof, and use thereof as herbicidal active substances
WO2022084278A1 (fr) 2020-10-23 2022-04-28 Bayer Aktiengesellschaft Dérivés de 1-(pyridyl)-5-azinylpyrazole et leur utilisation pour lutter contre la croissance de plantes indésirables
AU2021374785A1 (en) 2020-11-05 2023-06-15 Bayer Aktiengesellschaft [(1-phenyl-5-(heteroaryl)-1h-1,2,4-triazol-3-yl)oxy] acetic acid derivatives as safeners for the protection of useful plants and crop plants
WO2022096448A1 (fr) 2020-11-05 2022-05-12 Bayer Aktiengesellschaft Dérivés d'acide [(5-phényl-5-hétéroaryl-1h-pyrazol-3-yl) oxy] acétique en tant que phytoprotecteurs pour la protection de plantes utiles et de plantes cultivées
CA3200699A1 (fr) 2020-11-05 2022-05-12 Bayer Aktiengesellschaft Derives d'acide [(1,5-di(heteroaryle)-1h-1,2,4-triazole-3-yl)oxy] acetique et sels connexes, compositions utiles de protection des plantes ou des cultures, procedes de preparation, utilisation et compositions utiles de protection des plantes ou des cultures comprenant les derives
EP4240723A1 (fr) 2020-11-05 2023-09-13 Bayer Aktiengesellschaft Utilisation de dérivés d'acide [(1,5-diphényl-1h-pyrazol-3-yl)oxy]acétique et de leurs sels et compositions les contenant pour réduire les effets phytotoxiques de produits agrochimiques, en particulier d'herbicides, dans des plantes utiles et des plantes cultivées
CA3200680A1 (fr) 2020-11-05 2022-05-12 Bayer Aktiengesellschaft Derives d'acide [(1-phenyl-5-heteroaryl-1h-pyrazol-3-yl)oxy] acetique utilises servant de phytoprotecteurs pour la protection de plantes utiles et de plantes cultivees
CN116568136A (zh) 2020-11-05 2023-08-08 拜耳公司 作为保护有用植物和作物植物的安全剂的[(5-苯基-1-杂芳基-1h-三唑-3-基)氧基]乙酸衍生物
EP4026833A1 (fr) 2021-01-12 2022-07-13 Bayer Aktiengesellschaft 2-(het)arylmethylpyrimidine à effet herbicide
WO2022152728A1 (fr) 2021-01-15 2022-07-21 Bayer Aktiengesellschaft Compositions herbicides
EP4288418A1 (fr) 2021-02-04 2023-12-13 Bayer Aktiengesellschaft (2-hétéroaryloxyphényl)sulfonates substitués, leurs sels et leur utilisation comme agents herbicides
WO2022194843A1 (fr) 2021-03-19 2022-09-22 Bayer Aktiengesellschaft 1,2,4-thiadiazoles substitués, leurs sels et leur utilisation comme substances actives herbicides
WO2022194842A1 (fr) 2021-03-19 2022-09-22 Bayer Aktiengesellschaft 1,2,4-thiadiazoles substitués, leurs sels et leur utilisation comme substances actives herbicides
WO2022194841A1 (fr) 2021-03-19 2022-09-22 Bayer Aktiengesellschaft 1,2,4-thiadiazoles substitués, leurs sels et leur utilisation comme substances actives herbicides
EP4313943A1 (fr) 2021-03-22 2024-02-07 Bayer Aktiengesellschaft Pyrrolidin-2-ones substituées, leurs sels et leur utilisation en tant que substances actives herbicides
WO2022207494A1 (fr) 2021-03-30 2022-10-06 Bayer Aktiengesellschaft 3-(hétéro)aryl-5-chlorodifluorométhyl-1,2,4-oxadiazole en tant que fongicide
WO2022207496A1 (fr) 2021-03-30 2022-10-06 Bayer Aktiengesellschaft 3-(hétéro)aryl-5-chlorodifluorométhyl-1,2,4-oxadiazole en tant que fongicide
US20240239755A1 (en) 2021-04-27 2024-07-18 Bayer Aktiengesellschaft Substituted pyridazinones, salts or n-oxides thereof and their use as herbicidally active substances
WO2022253700A1 (fr) 2021-06-01 2022-12-08 Bayer Aktiengesellschaft Pyrroline-2-ones spécifiquement substituées et leur utilisation en tant qu'herbicides
UY39792A (es) 2021-06-02 2023-01-31 Bayer Ag Composiciones herbicidas que comprenden etofumesato y un protector, y usos de las mismas
EP4358718A1 (fr) 2021-06-25 2024-05-01 Bayer Aktiengesellschaft Acides (1,4,5-trisubstitués-1h-pyrazole-3-yl)oxy-2-alcoxy alkyle et leurs dérivés, leurs sels et leur utilisation en tant qu'agents herbicides
WO2023274869A1 (fr) 2021-06-29 2023-01-05 Bayer Aktiengesellschaft 3-(4-alcényl-phényl)-3-pyrrolino-2-ones et leur utilisation comme herbicides
EP4362680A1 (fr) 2021-07-02 2024-05-08 Bayer Aktiengesellschaft Compositions herbicides contenant de la cinméthyline et de l'éthofumesate
AR126252A1 (es) 2021-07-08 2023-10-04 Bayer Ag Amidas de ácido benzoico sustituidas
CA3228106A1 (fr) 2021-08-02 2023-02-09 Bayer Aktiengesellschaft Utilisation de compositions comprenant de l'ethofumesate et de la bixlozone dans des cultures de ble
CA3229299A1 (fr) 2021-08-17 2023-02-23 Bayer Aktiengesellschaft 1,2,4-thiadiazolyl nicotinamides substitues, leurs sels ou n-oxydes et leur utilisation comme substances actives herbicides
WO2023020963A1 (fr) 2021-08-17 2023-02-23 Bayer Aktiengesellschaft 1,2,4-thiadiazolyl nicotinamides substitués, leurs sels ou n-oxydes et leur utilisation comme substances actives herbicides
WO2023020962A1 (fr) 2021-08-17 2023-02-23 Bayer Aktiengesellschaft 1,2,4-thiadiazolyl nicotinamides substitués, leurs sels ou n-oxydes et leur utilisation comme substances actives herbicides
TW202328151A (zh) 2021-09-07 2023-07-16 德商拜耳廠股份有限公司 經取代之2,3-二氫[1,3]噻唑并[4,5-b]吡啶、其鹽及其作為除草活性物質之用途
TW202328150A (zh) 2021-09-07 2023-07-16 德商拜耳廠股份有限公司 經取代之噻唑并吡啶、其鹽及其作為除草活性物質之用途
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WO2024104952A1 (fr) 2022-11-16 2024-05-23 Bayer Aktiengesellschaft Cyclopropyloxyphényluraciles substitués et leurs sels, et leur utilisation comme principes actifs herbicides
WO2024104956A1 (fr) 2022-11-16 2024-05-23 Bayer Aktiengesellschaft Cycloalkylsulfanylphényluraciles substitués et leurs sels, et leur utilisation comme principes actifs herbicides
WO2024104954A1 (fr) 2022-11-16 2024-05-23 Bayer Aktiengesellschaft Cycloalkyloxyphényluraciles substitues et leurs sels, et leur utilisation comme principes actifs herbicides
WO2024104643A1 (fr) 2022-11-17 2024-05-23 Bayer Aktiengesellschaft Utilisation d'isotianil pour lutter contre plasmodiophora brassica
EP4417602A1 (fr) 2023-02-16 2024-08-21 Bayer AG Pyrazole carboxamides substitués, leurs sels et leur utilisation comme agents herbicides

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1543964A (en) * 1976-04-08 1979-04-11 Ici Ltd Method of antagonising herbicides on soyabean and cotton
IT1110460B (it) * 1977-03-02 1985-12-23 Ciba Geigy Ag Prodotti che favoriscono la crescita delle piante e prodotti che proteggono le piante a base di eteri di ossime e di esteri di ossime loro preparazione e loro impiego
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
CZ129493A3 (en) 1990-12-31 1994-03-16 Monsanto Co Elimination of pesticides influence on plants
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
US5129949A (en) * 1991-07-22 1992-07-14 American Cyanamid Company Herbicidal composition and method for safening herbicides in cereal crops using 1-carbethoxyethyl-3,6-dichloro-2-methoxybenzoate
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
US5596124A (en) * 1994-12-09 1997-01-21 American Cyanamid Company Method for safening herbicides in cereal crops using 5-aryloxy-1,2-(disubstituted)benzene compounds
AUPP041097A0 (en) * 1997-11-14 1997-12-11 Crown In The Right Of The State Of Western Australia, The Method for inducing stress tolerance in plant material
DE19853827A1 (de) * 1998-11-21 2000-05-25 Aventis Cropscience Gmbh Kombinationen aus Herbiziden und Safenern
DE19933897A1 (de) 1999-07-22 2001-01-25 Basf Ag Verfahren zur Erhöhung der Widerstandskraft von Kulturpflanzen gegen chemischen Stress
DE19936437A1 (de) * 1999-08-03 2001-02-08 Aventis Cropscience Gmbh Kombinationen aus Herbiziden und Safenern
AR031027A1 (es) * 2000-10-23 2003-09-03 Syngenta Participations Ag Composiciones agroquimicas
CA2480456C (fr) * 2002-04-04 2011-11-22 Valent Biosciences Corp. Composition herbicide amelioree
ATE496536T1 (de) * 2002-04-10 2011-02-15 Basf Se Verfahren zur erhöhung der widerstandskraft von pflanzen gegen die phytotoxizität von agrochemikalien
WO2004060067A1 (fr) * 2002-12-16 2004-07-22 Valent Biosciences Corporation Composition herbicide contenant un inhibiteur de ps-ii et un inducteur de sar

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005015994A1 *

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US8138118B2 (en) 2012-03-20
WO2005015994A1 (fr) 2005-02-24
US20050037922A1 (en) 2005-02-17
CN1829437A (zh) 2006-09-06
UA89033C2 (ru) 2009-12-25
EA200600357A1 (ru) 2006-08-25
DE10335726A1 (de) 2005-03-03
ZA200600090B (en) 2007-01-31
CA2534742A1 (fr) 2005-02-24
CR8200A (es) 2008-11-25
JP2007501197A (ja) 2007-01-25
KR20060120574A (ko) 2006-11-27
BRPI0413365A (pt) 2006-10-17
EA011454B1 (ru) 2009-04-28
AR045201A1 (es) 2005-10-19
RS20060039A (en) 2007-12-31
MXPA06001421A (es) 2006-05-15
CN1829437B (zh) 2011-03-30
IL173468A0 (en) 2006-06-11
AU2004264297B2 (en) 2011-02-03
AU2004264297A1 (en) 2005-02-24

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