EP1653804A1 - Utilisation d'aromates hydroxy comme phytoprotecteurs - Google Patents
Utilisation d'aromates hydroxy comme phytoprotecteursInfo
- 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
- Authority
- 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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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10335726A DE10335726A1 (de) | 2003-08-05 | 2003-08-05 | Verwendung von Hydroxyaromaten als Safener |
PCT/EP2004/008233 WO2005015994A1 (fr) | 2003-08-05 | 2004-07-23 | Utilisation d'aromates hydroxy comme phytoprotecteurs |
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WO2008007171A1 (fr) * | 2006-07-09 | 2008-01-17 | Techfields Biochem Co. Ltd | Promédicaments hydrosolubles à charge positive de l'aspirine |
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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 |
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-
2003
- 2003-08-05 DE DE10335726A patent/DE10335726A1/de not_active Withdrawn
-
2004
- 2004-07-23 MX MXPA06001421A patent/MXPA06001421A/es unknown
- 2004-07-23 BR BRPI0413365-0A patent/BRPI0413365A/pt not_active Application Discontinuation
- 2004-07-23 CN CN2004800217145A patent/CN1829437B/zh not_active Expired - Fee Related
- 2004-07-23 JP JP2006522272A patent/JP2007501197A/ja active Pending
- 2004-07-23 RS YUP-2006/0039A patent/RS20060039A/sr unknown
- 2004-07-23 AU AU2004264297A patent/AU2004264297B2/en not_active Ceased
- 2004-07-23 KR KR1020067002420A patent/KR20060120574A/ko not_active Application Discontinuation
- 2004-07-23 EA EA200600357A patent/EA011454B1/ru not_active IP Right Cessation
- 2004-07-23 UA UAA200602363A patent/UA89033C2/ru unknown
- 2004-07-23 CA CA002534742A patent/CA2534742A1/fr not_active Abandoned
- 2004-07-23 WO PCT/EP2004/008233 patent/WO2005015994A1/fr active Search and Examination
- 2004-07-23 EP EP04741232A patent/EP1653804A1/fr not_active Withdrawn
- 2004-08-03 AR ARP040102758A patent/AR045201A1/es not_active Application Discontinuation
- 2004-08-04 US US10/911,706 patent/US8138118B2/en not_active Expired - Fee Related
-
2006
- 2006-01-04 ZA ZA200600090A patent/ZA200600090B/en unknown
- 2006-01-18 CR CR8200A patent/CR8200A/es not_active Application Discontinuation
- 2006-01-31 IL IL173468A patent/IL173468A0/en unknown
Non-Patent Citations (1)
Title |
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See references of WO2005015994A1 * |
Also Published As
Publication number | Publication date |
---|---|
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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