WO2000035913A1 - Trifluoromethyl-4 oxadiazolyl-3 pyridines, leur procede de production, produits les contenant et leur utilisation comme produits de lutte contre les parasites - Google Patents

Trifluoromethyl-4 oxadiazolyl-3 pyridines, leur procede de production, produits les contenant et leur utilisation comme produits de lutte contre les parasites Download PDF

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WO2000035913A1
WO2000035913A1 PCT/EP1999/009684 EP9909684W WO0035913A1 WO 2000035913 A1 WO2000035913 A1 WO 2000035913A1 EP 9909684 W EP9909684 W EP 9909684W WO 0035913 A1 WO0035913 A1 WO 0035913A1
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compounds
spp
formula
trifluoromethyl
alkyl
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PCT/EP1999/009684
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German (de)
English (en)
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Sven Harmsen
Henricus Maria Martinus Bastiaans
Wolfgang Schaper
Jörg Tiebes
Uwe Döller
Daniela Jans
Ulrich Sanft
Waltraut Hempel
Maria-Theresia Thönessen
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Aventis Cropscience Gmbh
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Priority to EP99963446A priority Critical patent/EP1140922A1/fr
Priority to AU19741/00A priority patent/AU1974100A/en
Priority to JP2000588173A priority patent/JP2002532497A/ja
Publication of WO2000035913A1 publication Critical patent/WO2000035913A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/82—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 three ring hetero 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
    • A01N43/72—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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N47/02—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 no bond to a nitrogen atom
    • A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the invention relates to 4-trifluoromethyl-3-oxadiazolylpyridines, processes for their preparation, compositions containing them and their use for controlling animal pests, in particular insects, spider mites, ectoparasites and helminths.
  • the object of the present invention is to provide compounds having good insecticidal and acaricidal properties and, at the same time, low toxicity to mammals and aquatic organisms.
  • the invention therefore relates to 4-trifluoromethyl-3-oxadiazolylpyridine derivatives of the formula (I),
  • n 0 or 1
  • X is a single bond, a straight-chain alkylene group with 1, 2 or 3 C atoms or a branched alkylene group with 3 to 9 C atoms, where one or more H atoms can be replaced by F;
  • Y is -O-, -S-, -SO-, -SO 2 -, -O-CO-, -O-CO-O-, -SO 2 -O-, -O-SO 2 -, -NR 1 -, -NR 2 -CO-, -NR 3 -CO-O-, -NR 4 -CO-NR 5 -, -O-CO-CO-O-, -O-CO-NR 6 , -SO 2 - NR 7 , -NR 8 -SO 2 -;
  • R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are the same or different, independently of one another H, (C r C 10 ) alkyl, (C 2 -C 10 ) Alkenyl, (C 2 -C 10 ) alkynyl, (C 3 -C 8 ) cycloalkyl, (C 4 -C 8 ) cycloalkenyl, (C 6 -C 8 ) cycloalkynyl, heterocyclyl or - (CH 2 ) 1 ⁇ l - heterocyclyl, where each of the eight last-mentioned groups is optionally substituted one or more times, and where appropriate R and R 1 , R and R 2 , R and R 5 , R and R 6 , R and R 7 , R and R 8 or R and X together can also form a ring system; with the proviso that the compounds in which
  • m is preferably 0.
  • n is preferably 2.
  • X is preferably a single bond, CH 2 , CH 2 -CH 2 , CH 2 -CH (CH 3 ) or
  • Y is preferably -O-, -S-, -SO-, -SO 2 -, -O-CO-, -O-CO-O, -O-CO-NR 6 -,
  • R, R, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are preferably the same or different, independently of one another H, (C r C 6 ) alkyl, (C 2 -C 6 ) Alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 8 ) cycloalkyl, (C 4 -C 8 ) cycloalkenyl, (C 6 -C 8 ) cycloalkynyl, heterocyclyl, - (CH 2 ) 1 ⁇ -Heterocyclyl, the eight last-mentioned radicals optionally with one or more radicals from the group
  • R 6 , R and R 7 , R and R 8 or R and X together can also form a ring system.
  • Preferred for the construction of such ring systems are - (CH 2 ) 3 -, - (CH 2 ) 4 -, - (CH 2 ) 5 -, - (CH 2 ) 2 -O- (CH 2 ) 2 -, - (CH 2 ) 2 -NR 3 - (CH 2 ) 2 -, - (thiophene-3,4-diyl) -C (O) -, CH (imidazolyl-) CF 2 C (O) -, -CH (Me) CH 2 C (O) -, -CMe 2 CH 2 C (O) -, -CH (Me) CH (Me) C (O) -, -CH 2 CH 2 CH 2 C (O) -, -CH (Me) CH 2 CH 2 C (O) -, -CH (Me) CH 2 CH 2 C (O) -, -CH 2 CH (Me) CH 2 C (O) -, -CH 2
  • W is O or S.
  • R 9 is hydrogen
  • R, R 1 -R 8 H, (C r C ⁇ ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, heterocyclyl are particularly preferred, the four last-mentioned radicals optionally with one or more, preferably one to four, radicals from the group halogen, preferably F, CN, SiMe 3 , -O- (C r C 6 ) -alkyl, -S- (C, -C 6 ) -alkyl or - 0-CO- (C 1 -C 6 ) alkyl are substituted.
  • halogen includes fluorine, chlorine, bromine and iodine.
  • (C 1 -C 4 ) alkyl is an unbranched or branched
  • alkyl radicals with 1, 2, 3 or 4 carbon atoms such as the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical.
  • alkyl radicals with a larger range of carbon atoms are to be understood as an unbranched or branched saturated hydrocarbon radical which contains a number of carbon atoms which corresponds to this range specification.
  • the expression "(C 1 -C 6 ) alkyl” accordingly encompasses the abovementioned alkyl radicals and, for example, the pentyl, 2-methylbutyl, 1, 1-dimethylpropyl or hexyl radical.
  • (C 1 -C 10 ) alkyl means the aforementioned alkyl radicals and, for example, the nonyl, 1-decyl or 2-decyl radical.
  • alkyl group in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl -, Fluoromethyl, the difluoromethyl and the 1, 1, 2,2-tetrafluoroethyl group.
  • halogen atoms preferably chlorine or fluorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl -, Fluoromethyl, the difluoromethyl and the 1, 1, 2,2-tetrafluoroethyl group.
  • (C -, - C 4 ) alkoxy means an alkoxy group
  • Alkoxy groups are to be understood analogously, which comprise a larger range of carbon atoms.
  • alkenyl and alkynyl with a prefixed range of carbon atoms mean a straight-chain or branched hydrocarbon radical with a number of carbon atoms corresponding to this range, which contains at least one multiple bond, which can be located at any position of the unsaturated radical in question.
  • (C 2 -C 4 ) alkenyl thus stands for example for the vinyl, allyl, 2-methyl-2-propene or
  • Alkynyl stands for example for the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group.”
  • (C 2 -C 6 ) -alkynyl “includes the radicals mentioned above and, for example, the
  • 2-pentynyl or the 2-hexynyl group and “(C 2 -C 10 ) -alkynyl” means the radicals mentioned above and, for example, the 2-octynyl or the 2-decynyl group.
  • (C 3 -C 8 ) cycloalkyl stands for monocyclic alkyl radicals, such as the cyclopropyl
  • (C 3 -C 8 ) -cycloalkyl- (C r C 4 ) -alkyl is, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical and the expression "(C 1 - C 6 ) -alkyl- (C 3 -C 8 ) -cycloalkyl, for example 1-methyl-cyclopropyl-, 1-methyl-cyclopentyl-, 1-methyl-cyclohexyl-, 3-hexyl-cyclobutyl- and 4-tert.- To understand butyl-cyclohexyl radical.
  • "(C 1 -C 4 ) alkoxy- (C 1 -C 6 ) alkyloxy” means an alkoxy group as defined above which is substituted by a further alkoxy group, such as 1-ethoxyethoxy.
  • (C 3 -C 8 ) cycloalkoxy or "(C 3 -C 8 ) cycloalkylthio” is one of the (C 3 -C 8 ) cycloalkyl radicals mentioned above which is linked via an oxygen or sulfur atom , to understand.
  • (C 3 -C 8 ) cycloalkyl- (C 1 -C 6 ) alkoxy means, for example, cyclopropylmethoxy
  • (C 1 -C 4 ) alkyl (C 3 -C 8 ) cycloalkoxy stands for example for the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyciohexyloxy group.
  • (CC 6 ) -Alkylthio stands for an alkylthio group whose hydrocarbon radical has the meaning given under the expression "(C-CgJ-alkyl).
  • (C -C 6 ) alkylsulfionyl means, for example, the methyl, ethyl, propyl, isopropyl
  • (d-CgJ-alkylamino) stands for a nitrogen atom which is substituted by one or two, identical or different alkyl radicals of the above definition.
  • (CC 6 ) mono- or dialkylcarbamoyl means a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the expression "(C 1 -C 6 alkyl)" and which, in the case of two hydrocarbon radicals, is identical or can be different.
  • (C 1 -C 6 ) -dihaloalkylcarbamoyl means a carbamoyl group, the two (CC 6 ) -haloalkyl radicals as defined above or one and carries a (CC 6 ) alkyl radical as defined above.
  • (CC 6 ) alkanoyl stands for example for the acetyl, propionyl, butyryl or 2-methylbutyryl group
  • aryl is a carbocyclic, i.e. aromatic radical composed of carbon atoms and preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as phenyl, naphthyl or biphenylyl, preferably phenyl.
  • Aroyl therefore means an aryl radical as defined above which is bonded via a carbonyl group, such as e.g. the benzoyl group.
  • heterocyclyl preferably stands for a cyclic radical which can be completely saturated, partially unsaturated or completely unsaturated and which can be interrupted by at least one or more identical or different atoms from the group consisting of nitrogen, sulfur or oxygen, but not two Oxygen atoms may be directly adjacent and at least one carbon atom must be present in the ring, such as a residue of thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1, 3,4-oxadiazole, 1, 3 , 4-thiadiazole, 1, 3,4-triazole, 1, 2,4-oxadiazole, 1, 2,4-thiadiazole, 1, 2,4-triazole, 1, 2,3-triazole, 1, 2,3 , 4-tetrazole, benzo [b] thiophene, benzo [b] furan, indole, benzo [c] thiophene,
  • Heterocyclyl particularly preferably means a saturated, partially saturated or aromatic ring system with 3 to 6 ring members and 1 to 4 heteroatoms from the group O, S and N, where at least one carbon atom must be present in the ring.
  • Heterocyclyl very particularly preferably denotes a radical of pyridine, pyrimidine, (1, 2,4) -oxadiazole, (1, 3,4) -oxadiazole, pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1, 2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane and oxetane.
  • Aryl radical e.g. the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.
  • Arylthio means an aryl residue linked via a sulfur atom, e.g. the phenylthio or the 1- or 2-naphthylthio radical.
  • aryloxy means e.g. the phenoxy or 1- or 2-naphthyloxy radical.
  • Aryl- (C -C) alkylthio represents an aryl radical linked via an alkylthio radical, e.g. the benzylthio, naphthylmethylthio or the phenylethylthio radical.
  • the expression means a silicon atom bearing three identical or different alkyl radicals as defined above.
  • Stand analog C 6 dialkylsilyl "for a silicon atom which carries an aryl radical and two identical or different alkyl radicals as defined above," diaryi (C 1 -C 6 ) alkylsilyl "for a silicon atom which has one alkyl radical and two identical or different Carries aryl radicals as defined above, and "triarylsilyl" for a silicon atom bearing three identical or different aryl radicals as defined above.
  • the compounds of the general formula (I) have acidic or basic properties and can form salts. If the compounds of the general formula (I) carry, for example, groups such as hydroxyl, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts.
  • bases are, for example, hydroxides, carbonates, hydrogen carbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (CC 4 ) alkyl radicals and mono-, di- and trialkanolamines of (CC 4 ) alkanols.
  • acids are, for example, mineral acids, such as hydrochloric, sulfuric and phosphoric acids, organic acids, such as acetic acid or oxalic acid, and acidic salts, such as NaHSO 4 and KHSO 4 .
  • the salts obtainable in this way also have insecticidal, acaricidal and nematicidal properties.
  • the compounds of the general formula (I) can have one or more asymmetric carbon atoms or stereoisomers on double bonds. Enantiomers or diastereomers can therefore occur.
  • the invention encompasses both the pure isomers and their mixtures.
  • the mixtures of diastereomers can be separated into the isomers by customary methods, for example by selective crystallization from suitable solvents or by chromatography. Racemates can be separated into the enantiomers by customary methods.
  • the compounds according to the invention are prepared by methods known per se from the literature, as are described in standard works on organic synthesis, for example Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart.
  • the preparation takes place under reaction conditions which are known and suitable for the reactions mentioned. Use can also be made of variants which are known per se and are not mentioned here in detail.
  • the starting materials can also be formed in situ, in such a way that they are not isolated from the reaction mixture, but instead are immediately reacted further to give the compounds of the formula (I).
  • the radical XYR is as defined in formula (I) or corresponds to a precursor of such a radical.
  • an acid halide, an ester or an anhydride can be used as the activated derivative.
  • Suitable bases are amines, such as triethylamine, diisopropylethylamine, pyridine or lutidine, alkali metal hydroxides, alkali metal alcoholates, such as sodium ethanolate or potassium tert-butoxide, or alkyl metal compounds, such as butyllithium.
  • the reaction described can be carried out as a one-step process or as a two-step process, with compounds of the formula (IV) being run through:
  • Compounds of the formula (IV) can be cyclized by heating in an inert solvent to give the 1, 2,4-oxadiazoles at temperatures up to 180 ° C and by adding dehydrating reagents (e.g. Amberlyst).
  • dehydrating reagents e.g. Amberlyst
  • Compounds of the formula (IV) are also directly accessible from the acid of the formula (II) and amidoximes of the formula (III) by using a dehydrating reagent such as dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylamino-propyl) carbodiimide or N, N'-carbonyldiimidazole.
  • Haloalkyl-, hydroxyalkyl- and aminoalkyl-substituted oxadiazole derivatives of the formula (V) serve as central intermediates of ethers, thioethers and analogous derivatives,
  • Ethers of the formula (I) can be obtained by etherification of corresponding hydroxyl compounds, the hydroxyl compound advantageously first being converted into a corresponding metal derivative, for example by treatment with NaH, NaNH 2 , NaOH, KOH, Na 2 CO 3, into the corresponding alkali metal alcoholate. This can then be reacted with the corresponding alkyl halide, alkyl sulfonate or dialkyl sulfate, advantageously in an inert solvent such as acetone, 1, 2-dimethoxyethane, DMF or dimethyl sulfoxide, or with an excess of aqueous or aqueous-alcoholic NaOH or KOH at temperatures between about 20 ° C and 100 ° C.
  • the synthesis is accomplished by oxidation with an oxidizing agent, e.g. meta-chloroperbenzoic acid, by suitable choice of stoichiomethe and temperature.
  • an oxidizing agent e.g. meta-chloroperbenzoic acid
  • Collections of compounds of formula (I) which can be synthesized according to the above-mentioned scheme can also be produced in a parallelized manner, this being possible in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction, the work-up or the cleaning of the products or intermediate stages. Overall, this is understood to mean a procedure as described, for example, by SH DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, Escom 1997, pages 69 to 77.
  • a number of commercially available devices can be used for the parallel reaction and processing, for example from the companies Stern Corporation, Woodrolfe road, Tollesbury, Essex, CM9 8SE, England or H + P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleissheim, Germany or the company Radleys, Shirehill, Saffron Waiden, Essex, England.
  • Chromatography apparatus for example from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA, is available for the parallelized purification of compounds of the general formula (I) or of intermediate products obtained in the preparation.
  • Automation systems of this type can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
  • compounds of the general formula (I) can be prepared completely or partially by methods supported by solid phases.
  • individual intermediates or all intermediates in the synthesis or a synthesis adapted for the corresponding procedure are bound to a synthetic resin.
  • Solid-phase-assisted synthesis methods are adequately described in the specialist literature, for example Barry A. Bunin in "The Combinatorial Index", published by Academic Press, 1998.
  • the use of solid-phase-supported synthesis methods allows a number of literature-known protocols, which in turn are carried out manually or automatically can. For example, the "Tea bag method” (Houghten, US 4,631,211; Houghten et al., Proc. Natl. Acad.
  • the preparation according to the processes described here provides compounds of the formula (I) in the form of substance collections which are called libraries.
  • the present invention also relates to libraries which contain at least two compounds of the formula (I).
  • the compounds of the formula (I) are suitable, with good plant tolerance and favorable warm-blood toxicity, for combating animal pests, in particular insects, arachnids, helminths and molluscs, very particularly preferably for combating insects and arachnids which are in the
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp.
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp., Eutetranychus spp ..
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example Lepisma saccharina.
  • Collembola for example Onychiurus armatus.
  • Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Isoptera for example Reticulitermes spp .
  • Eurygaster spp. Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius proiixus, Triatoma spp .. From the order of the Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phoralonosiphum, spp.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae,
  • Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp ..
  • Heliothis spp. Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Cauleria Capellaella, Galleria mellononeella, Galleria mellononeella fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp ..
  • Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • Siphonaptera e.g. Xenopsylla cheopsis, Ceratophyllus spp ..
  • Arachnida e.g. Scorpio maurus
  • Latrodectus mactans From the class of the helminths e.g. Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola.
  • Gastropoda e.g. Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphala a spp., Bulinus spp., Oncomelania spp ..
  • the plant-parasitic nematodes which can be controlled according to the invention include, for example, the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-bile nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), heterodera and Globodera (cyst-forming nematodes such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) and the genera Radopholus such as Radopholus similis, Pratylenchus such as Pratyglenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus;
  • the root-parasitic soil nematodes such as, for example, those of the genera Meloidogyne (root-bile nematodes, such as Meloidogy
  • Tylenchulus such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus such as Rotylenchus robustus, Heliocotylenchus such as Haiiocotylenchus multicinctus, Belonoaimus such as Belonoaimus Trachususus longusus x longus.
  • the compounds of the invention can also be used to combat the nematode genera Ditylenchus (stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes such as Aphelenchoides ritzemabosi) and Anguina (flower nematodes such as Anguina tritici).
  • Ditylenchus stem parasites such as Ditylenchus dipsaci and Ditylenchus destructor
  • Aphelenchoides leaf nematodes such as Aphelenchoides ritzemabosi
  • Anguina flower nematodes such as Anguina tritici
  • the invention also relates to compositions, for example crop protection agents, preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluscicidal or fungicidal, particularly preferably insecticidal and acaricidal compositions which contain one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
  • crop protection agents preferably insecticidal, acaricidal, ixodicidal, nematicidal, molluscicidal or fungicidal, particularly preferably insecticidal and acaricidal compositions which contain one or more compounds of the formula (I) in addition to suitable formulation auxiliaries.
  • the agents according to the invention generally contain 1 to 95% by weight of the active compounds of the formula (I).
  • the active ingredient and the other additives are combined and brought into a suitable form of use.
  • the invention also relates to compositions, in particular insecticidal and acaricidal compositions, which contain the compounds of the formula (I) in addition to suitable formulation auxiliaries.
  • the agents according to the invention generally contain 1 to 95% by weight of the active compounds of the formulas (I). They can be formulated in different ways, depending on how it is specified by the biological and / or chemical-physical parameters. Possible formulation options include:
  • WP Wettable powder
  • EC emulsifiable concentrates
  • SL aqueous solutions
  • SC oil or water-based dispersions
  • SE suspoemulsions
  • SE suspoemulsions
  • DP dusts
  • mordants granules in the form of , Spray, elevator and adsorption granules
  • WG water-dispersible granules
  • ULV formulations microcapsules, waxes or baits.
  • the necessary formulation aids i.e. Carrier and / or surface-active substances, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Garriers", 2nd Ed., Darland Books, Caldwell N.J .; H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y .; Marsden, “Solvent Guide,” 2nd Ed., Interscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual", MC Publ.
  • Carrier and / or surface-active substances such as inert materials, surfactants, solvents and other additives
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or inert substance, but also wetting agents, for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, for example sodium lignosulfonate, 2,2'-dinaphthylmethane-6, Contain 6'- disulfonic acid sodium.
  • wetting agents for example polyoxethylated alkylphenols, polyoxethylated fatty alcohols, alkyl or alkylphenol sulfonates and dispersants, for example sodium lignosulfonate, 2,2'-dinaphthylmethane-6, Contain 6'- disulfonic acid sodium.
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons with the addition of one or more emulsifiers.
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
  • emulsifiers may be used, for example: calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid ester or Poiyoxethylensorbitester.
  • calcium alkylarylsulfonates such as Ca dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid ester or Po
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g. Talc, natural clays, such as kaolin, bentonite, pyrophillite or diatomaceous earth.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired as a mixture with fertilizers.
  • the active substance concentration in wettable powders is usually about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 5 to 80% by weight. Dust-like formulations usually contain 5 to 20% by weight % of active ingredient, sprayable solutions about 2 to 20 wt .-%. In the case of granules, the active substance content depends in part on whether the active compound is in liquid or solid form and which granulating agents, fillers, etc. are used.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
  • the concentrates which are commercially available, are diluted in the customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and sometimes also for microgranules using water. Dust-like and granulated preparations as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate varies. It can fluctuate within wide limits, e.g. between 0.0005 and 10.0 kg / ha or more of active substance, but it is preferably between 0.001 and 5 kg / ha of active substance.
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in mixtures with other active compounds, such as insecticides, attractants, standing antioxidants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the pesticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, formamidines, tin compounds and substances produced by microorganisms.
  • Preferred mix partners are: 1. from the group of phosphorus compounds
  • Alanycarb (OK-135), Aldicarb, 2-sec-butylphenylmethylcarbamate (BPMC), Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Benfuracarb, Ethiofencarb, Furathiocarb, HCN-801, Isoprocarb, Methomyl, 5-Methyl-m-cumenylbutyryl ( carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio (ethylideneamino) -N-methyl-N- (morpholinothio) carbamate (UC 51717), triazamate;
  • the active substance content of the use forms prepared from the commercially available formulations can be from 0.00000001 to 95% by weight of active substance, preferably between 0.00001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active compounds according to the invention are also suitable for combating endoparasites and ectoparasites in the veterinary field or in the field of animal husbandry.
  • the active compounds according to the invention are used here in a known manner, such as by oral use in the form of, for example, tablets, capsules, drinkers, granules, by dermal use in the form of, for example, dipping (dipping), spraying (spraying), pouring on (pour-on and spot) -on) and the pump and by parenteral use in the form of, for example, the injection.
  • the compounds of the formula (I) according to the invention can accordingly also be used particularly advantageously in animal husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese, etc.).
  • the compounds are administered to the animals orally. Since excretion in the faeces is effective, the development of insects in the faeces of the animals can be prevented very easily in this way.
  • the appropriate dosages and formulations depend in particular on the type and stage of development of the livestock and also on the infestation pressure and can be easily determined and determined using the usual methods.
  • the compounds can be used in cattle, for example, in doses of 0.01 to 1 mg / kg of body weight.
  • the active compounds of the formula (I) according to the invention have an outstanding systemic action.
  • the active ingredients can therefore also be introduced into the plants via parts of plants, both underground and above ground (roots, stems, leaves), if the active ingredients are applied in liquid or solid form to the immediate vicinity of the plant (e.g. granules in the soil application, application in flooded rice fields).
  • the active compounds according to the invention can be used in a particular way to treat vegetative and generative propagation material, such as, for example, seeds from, for example, cereals, vegetables, cotton, rice, sugar beet and other crops and ornamental plants, onions, cuttings and tubers from other vegetatively propagated crops. and ornamental plants.
  • the treatment for this can take place before the sowing or planting process (e.g. by special techniques of seed coating, by dressing in liquid or solid form or seed box treatment), during the sowing process or planting or after the sowing or planting process by special application techniques (eg seed row treatment).
  • the amount of active ingredient used can be according to Application fluctuate in a larger range. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil.
  • the compounds of formula (I) can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally distinguished by particularly advantageous properties, for example resistance to certain crop protection agents, resistance to plant diseases or pathogens causing plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, storability, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn
  • crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables e.g. of cereals, such as wheat, barley, rye, oats, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the invention therefore also relates to the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.
  • the use of the compounds according to the invention includes any other application in which compounds of the formula (I) act on the pests.
  • Such indirect applications can be, for example, the use of compounds which, for example in the soil, the plant or the pest, decompose or break down to give compounds of the formula (I).
  • amidoxime ester (4.0 g) was mixed with 80 ml of toluene and 60 ml of xylene and Amberlyst 15 (1.0 g). The reaction mixture was heated to 125 ° C for 6 h. The mixture was then filtered off with suction and the filtrate was concentrated in vacuo and purified by chromatography (silica gel, ethyl acetate / petroleum ether, 4: 1). Final stirring with n-heptane gave [5- (4'-trifluoromethylpyridin-3'yl) - [1, 2,4] oxdiazol-3-methyl] furfuryl sulfone as a light yellow solid (melting point 99 ° C.) .
  • the sodium sulfonate (0.95 g) described above was suspended in phosphorus oxychloride (30 ml) and heated to reflux for 5 hours. The excess phosphorus oxychloride was then distilled off and the remaining sulfonyl chloride was taken up in dichloromethane (10 ml). This suspension was mixed with ethyl methylamine (150 ml) and stirred for a further hour at room temperature.
  • reaction mixture was then concentrated, taken up in ethyl acetate, washed with water, dried (MgSO 4 ), filtered and concentrated.
  • a dusting agent is obtained by mixing 10 parts by weight of active ingredient and 90 parts by weight of talc as an inert substance and comminuting them in a hammer mill.
  • a wettable powder which is readily dispersible in water is obtained by adding 25 parts by weight of active compound, 65 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as the wetting agent. and dispersant mixes and grinds in a pin mill.
  • a dispersion concentrate which is readily dispersible in water is prepared by mixing 40 parts by weight of active compound with 7 parts by weight of a sulfosuccinic acid half-ester, 2 parts by weight of a lignosulfonic acid sodium salt and 51 parts by weight of water and in a attritor ground to a fineness of less than 5 microns.
  • An emulsifiable concentrate can be prepared from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexane as solvent and 10 parts by weight of oxyethylated nonylphenol (10 EO) as emulsifier.
  • Granules can be produced from 2 to 15 parts by weight of active ingredient and an inert granule carrier material such as attapulgite, pumice granules and / or quartz sand.
  • a suspension of the wettable powder from example b) having a solids content of 30% is expediently used and sprayed onto the surface of an attapulgite granulate, dried and mixed intimately.
  • the proportion by weight of the spray powder is about 5% and that of the inert carrier material is about 95% of the finished granulate.
  • Germinated field bean seeds Vicia faba
  • germ roots were transferred to amber glass bottles filled with tap water and then coated with about 100 black bean aphids (Aphis fabae). Plants and aphids were then immersed in an aqueous solution of the preparation to be tested and formulated for 5 seconds. After draining, the plants and animals were stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 3 and 6 days of storage, the effect of the preparation on the aphids was determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Examples Nos. 2/29, 2/43, 2/67, 2/6, 3/6, 3/50, 3/75 and 3 caused / 49 90-100% aphid mortality.
  • the leaves of 12 rice plants with a stem length of 8 cm were immersed for 5 seconds in an aqueous solution of the preparation to be tested and formulated. After draining, the rice plants treated in this way were placed in a petri dish and populated with about 20 larvae (L3 stage) of the leafhopper species Nilaparvata lugens. After closing the petri dish, it was stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 6 days of storage, the mortality of the leafhopper larvae was determined. At a concentration of 300 ppm (based on the content of active ingredient), the preparations according to Examples Nos. 2/97, 2/127, 2/153, 2/255, 3/50 and 3/75 brought about a 90-100% strength Mortality.
  • Germinated field bean seeds (Vicia faba) with germ roots were transferred to amber glass bottles filled with tap water.
  • Four milliliters of an aqueous solution of the preparation to be tested and formulated was pipetted into the amber glass vial.
  • the broad bean was heavily coated with about 100 black bean aphids (Aphis fabae).
  • the plant and animals were then stored in a climatic chamber (16 hours light / day, 25 ° C, 40-60% RH). After 3 and 6 days of storage, the root systemic effect of the preparation on the aphids was determined.
  • the preparations according to Examples No.

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Abstract

L'invention concerne des trifluorométhyl-4 oxadiazolyl-3 pyridines de formule générale (I), leur procédé de production, les produits les contenant ainsi que l'utilisation de ces composés pour lutter contre des animaux nuisibles, en particulier des insectes, des tétranyques, des ectoparasites et des helminthes. X et Y ont les significations indiquées dans la description.
PCT/EP1999/009684 1998-12-17 1999-12-09 Trifluoromethyl-4 oxadiazolyl-3 pyridines, leur procede de production, produits les contenant et leur utilisation comme produits de lutte contre les parasites WO2000035913A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99963446A EP1140922A1 (fr) 1998-12-17 1999-12-09 Trifluoromethyl-4 oxadiazolyl-3 pyridines, leur procede de production, produits les contenant et leur utilisation comme produits de lutte contre les parasites
AU19741/00A AU1974100A (en) 1998-12-17 1999-12-09 4-trifluoromethyl-3-oxadiazolyl pyridines, methods for the production thereof, agents containing these compounds, and their use as pesticides
JP2000588173A JP2002532497A (ja) 1998-12-17 1999-12-09 ４−トリフルオロメチル−３−オキサジアゾリルピリジン、その製造方法、その化合物を含有する薬剤、および農薬としてのその使用

Applications Claiming Priority (2)

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DE19858193.9 1998-12-17
DE1998158193 DE19858193A1 (de) 1998-12-17 1998-12-17 4-Trifluormethyl-3-oxadiazolylpyridine, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel

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WO2001047918A2 (fr) * 1999-12-23 2001-07-05 Aventis Cropscience Gmbh Derives d"azolyl-alkyl-azole, procedes pour leur production et leur utilisation comme produits antiparasitaires
WO2003044013A1 (fr) * 2001-11-21 2003-05-30 Sankyo Agro Company, Limited Derives de n-heteroarylnicotinamide
WO2004014881A3 (fr) * 2002-08-09 2004-05-27 Astrazeneca Ab Nouveaux composes
WO2004074272A1 (fr) * 2003-02-21 2004-09-02 Pharmacia & Upjohn Company Llc Agents anthelmintiques et compositions insecticides
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CN100425609C (zh) * 2001-11-21 2008-10-15 三共农业株式会社 N-杂芳基烟酰胺衍生物
US20100179189A1 (en) * 2006-11-15 2010-07-15 Hesheng Zhang Pyrroline derivatives against cell releasing tumor necrosis factor, preparation methods and uses thereof
EP2396321A2 (fr) * 2009-02-10 2011-12-21 Divergence, Inc. Compositions et procédés de lutte contre les nématodes
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DE102004022897A1 (de) * 2004-05-10 2005-12-08 Bayer Cropscience Ag Azinyl-imidazoazine
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JP5326424B2 (ja) * 2007-08-31 2013-10-30 住友化学株式会社 含フッ素有機硫黄化合物およびその有害節足動物防除剤
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WO2001047918A2 (fr) * 1999-12-23 2001-07-05 Aventis Cropscience Gmbh Derives d"azolyl-alkyl-azole, procedes pour leur production et leur utilisation comme produits antiparasitaires
WO2001047918A3 (fr) * 1999-12-23 2002-03-14 Aventis Cropscience Gmbh Derives d"azolyl-alkyl-azole, procedes pour leur production et leur utilisation comme produits antiparasitaires
WO2003044013A1 (fr) * 2001-11-21 2003-05-30 Sankyo Agro Company, Limited Derives de n-heteroarylnicotinamide
US7015236B2 (en) 2001-11-21 2006-03-21 Sankyo Agro Company, Limited N-heteroarylnicotinamide derivatives
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CN100425609C (zh) * 2001-11-21 2008-10-15 三共农业株式会社 N-杂芳基烟酰胺衍生物
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WO2004014881A3 (fr) * 2002-08-09 2004-05-27 Astrazeneca Ab Nouveaux composes
JP2006503009A (ja) * 2002-08-09 2006-01-26 アストラゼネカ アクチボラグ 代謝調節型グルタミン酸受容体−５の調節因子としての１，２，４−オキサジアゾール類
WO2004074272A1 (fr) * 2003-02-21 2004-09-02 Pharmacia & Upjohn Company Llc Agents anthelmintiques et compositions insecticides
AU2004303604B2 (en) * 2003-12-24 2011-03-24 Prosidion Limited Heterocyclic derivatives as GPCR receptor agonists
WO2005061489A1 (fr) * 2003-12-24 2005-07-07 Prosidion Limited Derives heterocycliques utilises comme agonistes des recepteurs gpcr
US8207147B2 (en) 2003-12-24 2012-06-26 Prosidion Limited Heterocyclic derivatives as GPCR receptor agonists
WO2007003960A1 (fr) * 2005-06-30 2007-01-11 Prosidion Limited Agonistes du gpcr
US20100179189A1 (en) * 2006-11-15 2010-07-15 Hesheng Zhang Pyrroline derivatives against cell releasing tumor necrosis factor, preparation methods and uses thereof
US8466191B2 (en) * 2006-11-15 2013-06-18 Hesheng Zhang Pyrroline derivatives against cell releasing tumor necrosis factor, preparation methods and uses thereof
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US9125410B2 (en) 2007-08-13 2015-09-08 Monsanto Technology Llc Compositions and methods for controlling nematodes
US9420788B2 (en) 2007-08-13 2016-08-23 Monsanto Technology Llc Compositions and methods for controlling nematodes
CN102307873A (zh) * 2009-02-10 2012-01-04 戴弗金思公司 用于控制线虫的组合物和方法
US9426995B2 (en) 2009-02-10 2016-08-30 Monsanto Technology Llc Compositions and methods for controlling nematodes
US9820486B2 (en) 2009-02-10 2017-11-21 Monsanto Technology Llc Compositions and methods for controlling nematodes
US8410023B2 (en) 2009-02-10 2013-04-02 Monsanto Technology Llc Compositions and methods for controlling nematodes
EP2396321A4 (fr) * 2009-02-10 2012-12-19 Divergence Inc Compositions et procédés de lutte contre les nématodes
EP2396321A2 (fr) * 2009-02-10 2011-12-21 Divergence, Inc. Compositions et procédés de lutte contre les nématodes

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EP1140922A1 (fr) 2001-10-10
DE19858193A1 (de) 2000-06-21
JP2002532497A (ja) 2002-10-02
CO5210920A1 (es) 2002-10-30
AU1974100A (en) 2000-07-03

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