EP0876351A1 - Derives de l'acide 2-pyrazolyloxyphenylacetique, agents les renfermant et leur utilisation pour lutter contre les champignons nuisibles et les parasites animaux - Google Patents

Derives de l'acide 2-pyrazolyloxyphenylacetique, agents les renfermant et leur utilisation pour lutter contre les champignons nuisibles et les parasites animaux

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Publication number
EP0876351A1
EP0876351A1 EP96943127A EP96943127A EP0876351A1 EP 0876351 A1 EP0876351 A1 EP 0876351A1 EP 96943127 A EP96943127 A EP 96943127A EP 96943127 A EP96943127 A EP 96943127A EP 0876351 A1 EP0876351 A1 EP 0876351A1
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EP
European Patent Office
Prior art keywords
compounds
alkyl
methyl
group
formula
Prior art date
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EP96943127A
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German (de)
English (en)
Inventor
Reinhard Kirstgen
Herbert Bayer
Norbert Götz
Wassilios Grammenos
Thomas Grote
Bernd Müller
Ruth Müller
Klaus Oberdorf
Michael Rack
Franz Röhl
Hubert Sauter
Eberhard Ammermann
Volker Harries
Gisela Lorenz
Siegfried Strathmann
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms

Definitions

  • 2-pyrazolyloxyphenylacetic acid derivatives compositions containing them and their use in combating harmful fungi and animal pests
  • the present invention relates to compounds of general formula I.
  • n 0, 1, 2, 3 or 4, it being possible for the radicals R 1 to be different if n is greater than 1;
  • Het is a pyrazole ring which carries the radical R 2 and can also carry one or, independently of one another, two substituents from the group: chlorine, bromine, methyl and trifluoromethyl;
  • R 1 is nitro, cyano, halo, C ⁇ -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C4-alkoxy, C ⁇ * -C 4 -haloalkoxy or C -.- C 4 alkylthio;
  • Phenyl or phenoxy which can each carry one to five halogen atoms and, optionally together with the halogen atoms, one or, independently of one another, two or three of the following substituents: -C 4 -alkyl,
  • n is greater than 1, a 1,3-butadiene-1,4-diyl group bonded to two adjacent carbon atoms of the phenyl radical, which in turn has one to four halogen atoms and, if appropriate together with the halogen atoms, one or, U.N- interdependent, two of the following substituents may gen tra ⁇ : nitro, cyano, C ⁇ 4 alkyl, C ⁇ -C 4 haloalkyl, C 1 -C 4 -alkoxy, C 4 -haloalkoxy and Ci-C 4 - Alkylthio;
  • R 2 is hydrogen or a directly or via a group (-CR 3 R 4 -), optionally substituted one or two-membered aromatic ring which, in addition to carbon atoms, contains one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or may contain an oxygen or sulfur atom as ring members, wherein
  • R 5 is C 1 -C 4 alkyl or C 2 -C 4 alkynyl.
  • the invention relates to compositions for controlling harmful fungi and animal pests which contain the compounds I or their salts and the use of the compounds I and their salts and the compositions comprising them.
  • 2-Heteroaryloxyphenylacetic acid derivatives with fungicidal, sometimes with insecticidal activity are known from the following publications: EP-A 178 824, EP-A 256 667, EP-A 398 692, EP-A 477 631, EP-A 513 580 , WO-A 94/10159 and EP-A 623 604.
  • agents for controlling harmful fungi and animal pests which contain the compounds I or their salts and the use of the compounds I and their salts and the compositions comprising them have been found for this purpose.
  • the compounds I can be obtained in various ways by processes known per se. Basically, it is irrelevant in their synthesis whether the grouping "O-Het-R 2 " or the grouping "Q" is first established.
  • the compounds I are obtainable via the compounds Z, which in turn are accessible by reacting compounds of the formula II with hydroxyheterocycles of the formula III.
  • 15 L is a leaving group customary for nucleophilic aromatic substitution, such as fluorine, chlorine, bromine or the nitro group;
  • This reaction is usually carried out at temperatures from 0 to 25 120, preferably 20 to 60 ° C.
  • Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl
  • Bases generally come into consideration: basic, inorganic compounds, for example alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride, alkali metal and alkaline earth metal carbonates such as potassium carbonate and 5 calcium carbonate, furthermore silver carbonate and alkali metal hydrogen carbonates such as sodium bicarbonate, metal organic compounds especially alkali metal alkyls such as methyl lithium, Butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alcoholates such as potassium tert-butoxide and dimethoxy magnesium.
  • alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride
  • alkali metal and alkaline earth metal carbonates such as potassium carbonate and 5 calcium carbonate
  • silver carbonate and alkali metal hydrogen carbonates such as sodium bicarbonate
  • Organic bases for example tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines are also suitable.
  • tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine
  • pyridine substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines are also suitable.
  • Sodium hydride, potassium carbonate and potassium tert-butoxide are particularly preferred.
  • the bases are generally used in equimolar amounts, in excess or, if appropriate, as a solvent.
  • reaction may be advantageous for the reaction to first treat the 15 compounds III with base and to react the resulting salt with the compound II.
  • reaction may also be advantageous for the reaction to use a catalytic amount of a crown ether, e.g. Add 18-Krone-6 or 20 15-Krone-5 or another usual phase transfer catalyst.
  • a catalytic amount of a crown ether e.g. Add 18-Krone-6 or 20 15-Krone-5 or another usual phase transfer catalyst.
  • phase transfer catalysts can ammonium and tetrafluoroborates such as benzyltriethylammonium, benzyl tributylammonium 25, tetrabutylammonium chloride, tetrabutylammonium Hexadecyltri- methylammoniumbromid or so ⁇ as phosphonium such as tetrabutylphosphonium chloride or tetraphenylphosphonium bromide used.
  • benzyltriethylammonium benzyl tributylammonium 25
  • tetrabutylammonium chloride tetrabutylammonium Hexadecyltri- methylammoniumbromid or so ⁇
  • phosphonium such as tetrabutylphosphonium chloride or tetraphenylphosphonium bromide used.
  • the starting materials II required for the preparation of the compounds I are known from the literature.
  • the starting materials III are also known from the literature or can be prepared by the processes described there f1-Hvdroxypyrazole: Liebigs. Ann. 1995, page 1563; 3-Hvdroxyoyrazole: J. Heterocycl.
  • Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, alcohols such as methanol, Ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, particularly preferably methanol, toluene and tetrahydrofuran.
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene
  • ethers such as diethyl ether, diisopropyl ether, ter
  • the compounds I can be obtained as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures are obtained in the synthesis, it is generally not absolutely necessary to separate the isomers, since the individual isomers are partially suitable for use or during use (for example under light, acid or Base action) can convert into each other. Corresponding conversions can also take place after use, for example in the treatment of plants, in the treated plant or in the harmful fungus or animal pest to be controlled.
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the (OCH 3 ) or (CH 3 ) - Group in relation to the COOCH 3 or CONHCH3 group).
  • the invention also includes the salts of the acid-resistant compounds I which contain basic centers, especially basic nitrogen atoms, in particular with mineral acids such as sulfuric acid and phosphoric acid or Lewis acids such as zinc chloride.
  • the type of salt is not important.
  • Such salts, which are suitable for agricultural purposes, are particularly significant.
  • the salts of the compounds I are accessible in a manner known per se, above all by reacting the corresponding compounds I with the acids mentioned in water or an inert organic solvent at temperatures from -80 to 120, preferably 0 to 60 ° C. .
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-C ⁇ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl,
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,
  • Chlorodifluoromethyl 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro 2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
  • Alkoxy straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via an oxygen atom (-0-), for example Ci-C ⁇ -alkoxy such as methyloxy, ethyloxy, propyloxy, 1-methylethyloxy, butyloxy , 1-methyl-propyloxy, 2-methylpropyloxy, 1,1-dimethylethyloxy, pentyloxy, l-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy, 1, 1 -Dimethylpropyloxy, 1,2-dimethylpropyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy
  • Halogenalkoxy straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, and where these groups are bonded to the skeleton via an oxygen atom;
  • Alkylthio straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms as mentioned above, which are bonded to the structure via a sulfur atom (-S-), e.g. Ci-C ⁇ -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbuty
  • the mono- or dinuclear aromatic or heteroaromatic systems mentioned for the radicals can in turn be partially or completely halogenated, i.e. the hydrogen atoms of these groups can be partially or completely replaced by halogen atoms such as fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine.
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -C ⁇ - alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl or 1-pentenyl;
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 4 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl or l-methyl-2- propinyl;
  • Alkylsulfonyl straight-chain or branched alkyl groups, as mentioned above, having 1 to 6 or 10 carbon atoms, which are bonded to the skeleton via a sulfonyl group (-S0 2 -);
  • C ⁇ ⁇ C 4 haloalkyl as mentioned above, preferably Trichlor ⁇ methyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl;
  • -C-C 4 alkoxy preferably methoxy, ethoxy, 1-methylethoxy and 1, 1-Dirnethylethoxy, especially methoxy;
  • C 1 -C 4 -haloalkoxy especially C 1 -C 2 -haloalkoxy, preferably difluoromethyloxy, trifluoromethyloxy and 2,2,2-trifluoroethyloxy, especially difluoromethyloxy;
  • -C-C 4 alkylthio preferably methylthio and 1-methylethylthio, especially methylthio
  • C 1 -C 4 alkylamino such as methylamines, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino and 1,1-dimethylethylamino, preferably methylamino and 1, 1-dimethylethylamino, especially methylamino,
  • Di-C ⁇ -C 4 alkylamino such as N, N-dimethylamino, N, N-diethylamino, N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N- Di- (l-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1, l-dimethylethyl) amino, N-ethyl-N-methylamino, N-methyl- N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methyl propyl) amino, N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N
  • Ci-Ce-alkylcarbonyl such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3- Methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbon
  • Cj-C ⁇ -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propyloxycarbonyl, 1-methylethoxycarbonyl, butyloxycarbonyl, 1-methylpropyloxycarbonyl, 2-methylpropyloxycarbonyl, 1, 1-dimethylethoxycarbonyl, pentyloxycarbonyl, 1-methylbutyloxycarbonyl, 2-methyl- butyloxycarbonyl, 3-methylbutyloxycarbonyl, 2,2-dimethylpropyloxycarbonyl, 1-ethylpropyloxycarbonyl, hexyloxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropyloxycarbonyl, 1-methylpentyloxycarbonyl, 2-methylpentyloxycarbonyl, 3-methylpentyloxycarbonyl 4-methylpentyloxycarbonyl, 1, 1-dimethylbutyloxycarbonyl, 1,2-dimethylbutyloxycarbony
  • Ci-C ⁇ -alkylaminocarbonyl such as methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl, 1, 1-dimethylethylaminocarbonyl, pentylaminocarbonyl, 1-methylbutylyl, 1-methylbutylyl, 1-methylbutylyl, 1-methylbutylyl, 1-methyl-butyl Methyl-butylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylp
  • Di-Ci-C ⁇ -alkylaminocarbonyl especially Di-C ⁇ -C 4 alkylaminocarbonyl such as N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di-propylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl , N, N-Di-butylaminocarbonyl, N, N-Di- (1-methylpropyl) aminocarbonyl, N, N-Di- (2-methylpropyl) aminocarbonyl, N, N-Di- (1,1-dimethylethyl) amino ⁇ carbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylamino ⁇ carbonyl, N-methyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1
  • Ci-C ⁇ -alkylcarboxyl such as methylcarboxyl, ethylcarboxyl, propylcarboxyl, 1-methylethylcarboxyl, butylcarboxyl, l-methylpropylcarboxyl, 2-methylpropylcarboxyl, 1,1-dimethylethylcarboxyl, pentylcarboxyl, 1-methylbutylcarboxyl, 2-methylbutylcarboxyl, 3-methylbutylcarboxyl, 1, 1-dimethylpropylcarboxyl, 1,2-dimethylpropylcarboxyl, 2,2-dimethylpropylcarboxyl, 1-ethylpropylcarboxyl, hexylcarboxyl, 1-methylpentylcarboxyl, 2-methylpentylcarboxyl, 3-methylpentylcarboxyl, 4- Methylpentylcarboxyl, 1,1-dimethylbutylcarbox
  • Ci-C ⁇ -alkylcarbonylamino such as methylcarbonylamino, ethylcarbonylamino, propylcarbonylamino, 1-methylethylcarbonylamino, butylcarbonylamino, 1-methylpropylcarbonylamino, 2-methylpropylcarbonylamino, 1,1-dimethylethylcarbonylamino, pentylcarbonylamino, 1-methylbutylamyl, 2-methylbutylamyl, 2-methyl-butyl 3-methylbutylcarbonylamino, 2, 2-dimethylpropylcarbonylamino, 1-ethylpropy1-carbonylamino, hexylcarbonylamino, 1,1-dimethylpropylcarbonylamino, 1,2-dimethylpropylcarbonylamino, 1-methylpentylcarbonylamino, 2-methylpentylcarbonylamino, 3-methylpentylcarbonyl Methylpenty
  • C 3 -C 7 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, preferably cyclopropyl, cyclopentyl and cyclohexyl, in particular cyclopropyl;
  • C 3 -C 7 cycloalkoxy such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, preferably cyclopentyloxy and cyclohexyloxy, especially cyclohexyloxy;
  • C 3 -C 7 cycloalkylthio such as cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio and cycloheptylthio, preferably cyclohexylthio;
  • C 3 -C 7 cycloalkylamino such as cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino and cycloheptylamino, preferably cyclopropylamino and cyclohexylamino, in particular cyclopropylamino;
  • Heterocyclyl or heterocyclyloxy, heterocyclylthio and heterocyclyllamino three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or .
  • Heterocyclyloxy via an oxygen atom or (Heterocyclylthio) via a sulfur atom or (Heterocyclylamino) via a nitrogen atom
  • Two adjacent radicals on R 2 can have the meaning of an oxy-C 1 -C 2 -alkylidoxy chain, optionally substituted with fluorine and / or chlorine, such as, for example, -O-CH 2 -0, -0-CF 2 - 0-, -O-CCI 2 -O-, -0-CH 2 CH 2 -0-, -0-CCl 2 CCl 2 -0- or -0-CF 2 CF 2 -0-, or one
  • C 3 -C 4 alkylidene chain such as propylidene or butylidene.
  • Het a pyrazole ring which carries the radical R 2 and can also carry one or two substituents from the group: chlorine, bromine, methyl and trifluoromethyl;
  • R 1 is halogen, C ⁇ -C 4 -alkyl, C 2 haloalkyl, C ⁇ -C 2 alkoxy, C ⁇ -C 2 -haloalkoxy or C ⁇ -C 2 -alkylthio;
  • Compounds I and their salts in which the variables have the following meanings are particularly preferred:
  • Het a pyrazole ring which carries the radical R 2 and can also carry one or two substituents from the group: chlorine, bromine, methyl and trifluoromethyl;
  • R 1 is halogen, C ⁇ -C4 ⁇ alkyl, C ⁇ ⁇ C 2 haloalkyl, C ⁇ -C 2 -alkoxy, C 2 -haloalkoxy or C ⁇ -C 2 -alkylthio;
  • Het a pyrazole ring which carries the radical R 2 and can also carry one or two substituents from the group: chlorine, bromine, methyl and trifluoromethyl;
  • R 1 is halogen, C ⁇ -C4 ⁇ alkyl, C * .- C 2 haloalkyl, C ⁇ -C 2 -alkoxy, C 2 -haloalkoxy or C ⁇ -C 2 -alkylthio;
  • n 0 or 1.
  • R 2 for an optionally subst. mononuclear or dinuclear aromatic radical which, in addition to carbon atoms, can contain one to four nitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atom or an oxygen or sulfur atom as ring members.
  • compounds I are also preferred in which R 2 for optionally subst.
  • Pyridyl or pyrimidyl which has a
  • R 2 represents optionally substituted phenyl or benzyl.
  • R 2 represents optionally substituted phenyl or benzyl.
  • Substi ⁇ tuenten of the phenyl radical and the phenyl ring in benzyl come in these cases, preferably halogen, cyano, C 4 alkyl, C 1 -C 4 -alkoxy, C 2 haloalkyl, C ⁇ -C 2 haloalkoxy, C 1 -C 4 alkoxycarbonyl, phenyl and oxy-C 1 -C 2 -alkylidenoxy in consideration.
  • R 2 represents an optionally substituted six-ring heteroaromatic such as pyridyl and pyrimidyl.
  • R 2 represents an optionally substituted six-ring heteroaromatic such as pyridyl and pyrimidyl.
  • a substituent of the six-ring heteroaromatic are preferably cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 2 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 2 haloalkoxy and phenyl.
  • radicals tV and R 2 have the meanings which correspond in each case to one line of Table A.
  • the compounds I are suitable for controlling harmful fungi and animal pests.
  • Suitable formulation aids are e.g. solid or liquid carriers, surfactants and adhesives.
  • Liquid carriers are understood to mean liquid solvents such as water and organic solvents, the latter having the function of an auxiliary solvent, especially when water is used as the solvent.
  • organic solvents aromatics such as xylene, toluene and alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes and methylene chloride, aliphatic hydrocarbons such as cyclohexane and paraffins, e.g. Mineral oil fractions, alcohols such as
  • ketones such as acetone, methyl ethyl ketone, methyl iso-butyl ketone and cyclohexanone
  • aprotic dipolar solvents such as dimethylformamide, N-methyl-2-pyrrolidone and dimethyl sulfoxide.
  • suitable solid carriers are: natural rock powder and mineral earths such as silicas, silicates, kaolins, clays, bolus, loess, talc, chalk, limestone, lime, dolomite, magnesium oxide, quartz, attapulgite, montmorillonite and diatomaceous earth; synthetic rock flour such as highly disperse silica or flour made of synthetic aluminum oxide and synthetic silicates.
  • Solid carriers particularly suitable for granules are, for example: broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite; synthetic granules made from inorganic and organic flours; Granules made from organic material such as sawdust, coconut shells, corn cobs or tobacco stalks.
  • Suitable surface-active agents are nonionic and anionic emulsifiers / foam-generating agents and dispersants:
  • Fatty acid polyoxyethylene esters such as lauryl alcohol polyoxyethylene ether acetate
  • Alkyl polyoxyethylene or polyoxypropylene ether for example of isotridecyl alcohol and fatty alcohol polyoxyethylene ether,
  • Alkylaryl alcohol polyoxyethylene ethers such as octylphenol polyoxyethylene ether, Tributylphenol polyoxyethylene ether, ethoxylated iso-octyl, octyl or nonylphenol or castor oil,
  • Sorbitol esters arylsulfonic acids, alkylsulfonic acids, alkylsulfuric acids,
  • Alkali, alkaline earth and ammonium salts of arylsulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, alkyl sulfonic acids, alkylarylsulfonic acids, alkyl, lauryl ether and fatty alcohol sulfuric acids, fatty acids, sulfated hexa-, hepta- and octadecanols and fatty alcohol glycol ethers,
  • Methyl cellulose Methyl cellulose.
  • Suitable adhesives are: carboxymethyl cellulose; natural and synthetic powdery, granular or latex-shaped polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, natural phospholipids such as cephalins and lecithins, synthetic phospholipids.
  • the agents can contain one or more representatives of the following groups of substances: dyes, other known active substances, trace nutrients and other additives.
  • Suitable dyes are, for example, inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue, and also organic pigments such as alizine, azo and metal phthalocyanine dyes.
  • Other known active ingredients include other fungicides as well as insecticides, acaricides, herbicides and growth regulators.
  • Trace nutrients are, for example, salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Addi ⁇ tive are about mineral and vegetable oils suitable.
  • the agents can moreover be mixed with other, practically important mixing partners such as fertilizers or other finished agents containing active ingredients.
  • the agents are prepared in a manner known per se, namely as a function of the chemical and physical properties of the substances used, for example by mixing, joint grinding, spraying, extruding, granulating or dissolving in water, the latter, if appropriate, with the aid of a organic Solvent. Powders, materials for spreading and dusts can be obtained, for example, by mixing or grinding the compounds I together with a solid carrier.
  • the agents are e.g. solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols or very fine encapsulations in polymeric substances or in seed coating compositions.
  • the agents which are generally available as concentrates are optionally dissolved, diluted, etc. as usual, in the case of wettable powders, water-dispersible granules, emulsifiable concentrates, dispersions and sometimes also in the case of microgranules, normally using water. Dust-like and granulated preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the agents are applied in a manner known per se, for example by spraying, atomizing, dusting, scattering or
  • the plants are usually sprayed or dusted with the agents. Alternatively or additionally, the seeds of the plants are treated in a manner known per se.
  • an aqueous dispersion of 20 parts by weight of a compound I according to the invention 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil;
  • V a mixture, ground in a hammer mill, of 80 parts by weight of a compound I according to the invention, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight Splitting powdered silica gel: by finely distributing the mixture in water, a spray liquor is obtained;
  • IX a stable oily dispersion of 20 parts by weight of a compound I according to the invention, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde Condensates and 68 parts by weight of a paraffinic mineral oil.
  • the compounds I, their salts and the agents according to the invention are notable for excellent activity against a broad spectrum of harmful fungi (phytopathogenic fungi), in particular from the class of
  • the compounds I, their salts and the agents according to the invention are used by mixing the harmful fungi, their habitat or the seeds, plants, surfaces, materials or areas to be protected against fungal attack with a fungicidally effective amount of the agents or the compounds I or treated their salts.
  • the application can take place before or after the infestation by the fungi.
  • the agents according to the invention and the compounds I are particularly suitable for controlling the following plant diseases:
  • Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton, rice and lawn, cereals and sugar cane, Ustilago , Venturia inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, ornamental plants and vegetables, Cercospora arachidicola on peanuts, Pseudocercosporella herpotsteoid on wheat, geranium Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on vines,
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.01 and 2.0 kg of active ingredient per ha.
  • compositions according to the invention can also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc ethylene diamine bis-dithiocarbamate, tetramethylthiurium dibiammamodisulfide ), Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis- (thiocarbamoyl) disulfide;
  • Nitroderivatives such as dinitro- (1-methylheptyl) phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate, 5-nitro-isophthalate - acid di-isopropyl ester;
  • heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0, O-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis - (dimethylamino) phosphinyl] -3-phenyl-1,2, 4-triazole, 2,3-dicyano-l, 4-dithioanthraquinone, 2-thio-l, 3-dithiolo [4, 5-b] quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benz ⁇ imidazole, N- (1,1,2,2-tetrachloroethyl
  • fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) -N -furoyl (2) - alaninate, DL-N- (2,6-dimethyl-phenyl) -N- (2 * -methoxyacetyl) -alanine-methyl ester, N- (2,6-dimethylphenyl) -N-chloroacetyl -D, L-2-amino-butyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) -alanine methyl ester, 5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2, 4-diox
  • Strobilurins such as methyl-E-methoximino- [ ⁇ - (o-tolyloxy) -otolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy] phenyl ⁇ -3-methoxyacrylate,
  • Methyl-E-methoximino- [ ⁇ - (2-phenoxyphenyl)] acetamide Methyl-E-methoximino- [ ⁇ - (2-phenoxyphenyl)] acetamide
  • Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-6 -cyclopropyl-pyrimidin-2-yl) aniline.
  • Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile, cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) -acrylic acid morpholide,
  • the compounds of formula I are also suitable for effectively combating animal pests, especially from the class of insects, arachnids and nematodes. They can be used as pesticides in crop protection as well as in the hygiene, storage protection and veterinary sectors.
  • the harmful insects include, for example, Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticuluraura, fumone chorionistana, Cheimatobella, Cheimatobella occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus,
  • Eupoecilia ambiguella Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cuninellaia, malomyellella, Hyponomeutella malaria, Hyponomeutella mala , Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Polis buophorella, Polis flophorella, Polis flammellaida, Polis
  • dipterous insects for example Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria Contarinia sorghicola, Cordylobia, anthropogenic pophaga, Culex pipiens, Dacus cucurbitae, oleae Dacus, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cupatausina, Musculica pata, Lycili
  • Thrips for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
  • From the order of the hymenoptera for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
  • Heteroptera From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucoptems, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor.
  • suckers for example Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypy, Dreianafiaisolumiaia, Dreianafusiaolaia, Dreianafusiaolaia, Dreyfusiaolaia Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida
  • Orthoptera From the order of the straight-wingers (Orthoptera), for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinisuspti, melanoplusi, melanoplusi, melanoplus americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus, Tachycines asynamorus.
  • Orthoptera for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexi
  • arachnids such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcop
  • root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita
  • Belonolaimus longicaudatus Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidorus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivusususiushylenchhylenchhylenchychnidchychnylchnatechychnidus Pratylenchus goodeyi.
  • the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
  • they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • the amount of active ingredient used to control pests is 0.1 to 2.0, preferably 0.2 to 1.0, kg / ha under field conditions.
  • the active ingredients were in the form of a 20% emulsion in a mixture of 10 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight.
  • % Emulphor® EL Emulphor® EL (Emulan® EL, emulsifier based on ethoxylated fatty alcohols) is prepared and diluted with water at the desired concentration. The evaluation was done visually.
  • the active ingredients were:
  • Nekanil® LN Litensol® AP6, wetting agent with Emulsifying and dispersing action based on ethoxylated alkylphenols
  • Emulphor® EL Emulphor® EL

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Composés de formule générale (I), ainsi que leurs sels, où les variables ont les significations ci-après: n vaut 0, 1, 2, 3 ou 4, les restes R1 pouvant être différents si n est supérieur à 1; Q est -C(=CHCH¿3?)-COOCH3, -C(=CHOCH3)-COOCH3, -C(=NOCH3)-COOCH3 ou -C(=NOCH3)-NH(CH3); Het est un noyau pyrazolique éventuellement substitué; R?1¿ est un nitro, cyano, halogène, alkyle en C¿1?-C4 halogénoalkyle en C1-C4, alkoxy en C1-C4, halogénoalkoxy en C1-C4, alkylthio en C1-C4, ou un phényle ou phénoxy éventuellement substitué ou, dans la mesure où n est supérieur à 1, un groupe 1,3 butadiène-1,4-diyle éventuellement substitué, lié à deux atomes de carbone voisins du reste phényle; R?2¿ est un hydrogène ou un cycle aromatique carbocyclique ou hétérocyclique à un ou deux noyaux, éventuellement substitué, lié au reste Het, soit directement, soit par l'intermédiaire d'un groupe (-CR?3R4-) [R3, R4¿ = H ou alkyle ou -CR3R4- = (-C(=O)-) ou (-C(=NOR?5)-); R5¿ = alkyle ou alkinyle]. L'invention concerne en outre les agents renfermant les composés précités, ainsi que l'utilisation des composés (I) et desdits agents pour lutter contre les champignons nuisibles et les parasites animaux.
EP96943127A 1995-12-27 1996-12-16 Derives de l'acide 2-pyrazolyloxyphenylacetique, agents les renfermant et leur utilisation pour lutter contre les champignons nuisibles et les parasites animaux Withdrawn EP0876351A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19548786A DE19548786A1 (de) 1995-12-27 1995-12-27 2-Pyrazolyloxy- und 2-Triazolyloxyphenylessigsäure-Derivate, sie enthaltende Mittel und ihre Verwendung zur Bekämpfung von Schadpilzen und tierischen Schädlingen
DE19548786 1995-12-27
PCT/EP1996/005633 WO1997024332A1 (fr) 1995-12-27 1996-12-16 Derives de l'acide 2-pyrazolyloxyphenylacetique, agents les renfermant et leur utilisation pour lutter contre les champignons nuisibles et les parasites animaux

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EP0876351A1 true EP0876351A1 (fr) 1998-11-11

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US (1) US6075149A (fr)
EP (1) EP0876351A1 (fr)
JP (1) JP2000502686A (fr)
AU (1) AU1195697A (fr)
CO (1) CO4750759A1 (fr)
DE (1) DE19548786A1 (fr)
WO (1) WO1997024332A1 (fr)
ZA (1) ZA9610841B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2292606A1 (fr) 2001-02-20 2011-03-09 Sagami Chemical Research Center Dérivé du pyrazole, son intermédiaire et herbicide contenant celui-ci en tant que principe actif

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ246603A (en) * 1992-01-29 1996-10-28 Basf Ag Carbamate derivatives and fungicidal compositions thereof
DE19804486A1 (de) 1998-02-05 1999-08-12 Basf Ag 2-(Pyrazolyloxy)-pyridin-3-ylessigsäure- Derivate, sie enthaltende Mittel und ihr
CN1305858C (zh) * 2004-02-20 2007-03-21 沈阳化工研究院 取代唑类化合物及其制备与应用
CN100427481C (zh) * 2005-05-26 2008-10-22 沈阳化工研究院 一种芳基醚类化合物及其制备与应用
CN103387540B (zh) * 2012-05-10 2015-10-14 中国中化股份有限公司 一种成盐法制备唑菌酯的方法

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Publication number Priority date Publication date Assignee Title
GB8619236D0 (en) * 1986-08-06 1986-09-17 Ici Plc Fungicides
DE4116090A1 (de) * 1991-05-17 1992-11-19 Basf Ag (alpha)-phenylacrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen und schadpilzen
FR2682379B1 (fr) * 1991-10-09 1994-02-11 Rhone Poulenc Agrochimie Nouveaux phenylpyrazoles fongicides.
KR970006238B1 (en) * 1994-03-15 1997-04-25 Korea Res Inst Chem Tech Propenoic ester derivatives having 4-hydroxy pyrazole group

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See references of WO9724332A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2292606A1 (fr) 2001-02-20 2011-03-09 Sagami Chemical Research Center Dérivé du pyrazole, son intermédiaire et herbicide contenant celui-ci en tant que principe actif

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WO1997024332A1 (fr) 1997-07-10
CO4750759A1 (es) 1999-03-31
JP2000502686A (ja) 2000-03-07
AU1195697A (en) 1997-07-28
US6075149A (en) 2000-06-13
ZA9610841B (en) 1998-06-23
DE19548786A1 (de) 1997-07-03

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