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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
  • C07C381/06—Compounds containing sulfur atoms only bound to two nitrogen atoms
  • C07C381/08—Compounds containing sulfur atoms only bound to two nitrogen atoms having at least one of the nitrogen atoms acylated
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
  • A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
  • A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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  • 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
  • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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  • 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
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  • 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
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
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  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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  • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
  • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
  • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
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  • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
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  • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
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  • C07C313/08—Sulfenic acids; Derivatives thereof
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Definitions

• the present invention relates to a novel haloalkene compound useful as an active ingredient of a pesticide.
• BACKGROUND ART WO03/84927, WO04/52872 and EP432861 disclose haloalkene compounds having certain specific chemical structures, respectively. However, they do not disclose or suggest haloalkene compounds of the after-mentioned formula (I) .
• the present invention relates to a haloalkene compound represented by the formula (I) or its salt:
• the pesticide containing, as an active ingredient, the novel haloalkene compound of the formula (I) has an extremely high pesticidal effect against pests at a low dose and at the same time has safety to crop plants, the natural enemy to pests, or mammals.
• the respective substituents for the alkyl which may be substituted, the alkenyl which may be substituted, the alkynyl which may be substituted, the cyclic hydrocarbon group which may be substituted, or the 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, for Q, may, for example, be W.
• the number of substituents K may be one or more, and if more, they may be the same or different.
• the number of substituents M 1 may be one or more, and if more, they may be the same or different.
• Each of M 2 and M 3 may, for example, be a hydrogen atom, alkyl which may be substituted by M 5 , alkenyl which may be substituted by M 5 , alkynyl which may be substituted by M 5 , a cyclic hydrocarbon group which may be substituted by M 1 , a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above .
• M 4 may, for example, be alkyl which may be substituted by M 5 , alkenyl which may be substituted by M 5 , alkynyl which may be substituted by M 5 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• M 5 may, for example, be halogen, alkoxy which may be substituted by M 1 , alkylthio which may be substituted by M 1 , alkylsulfinyl which may be substituted by M 1 , alkylsulfonyl which may be substituted by M 1 , -M 6 , -OM 6 or -SM 6 .
• the number of substituents M 5 may be one or more, and if more, they may be the same or different.
• M 1 is as defined above .
• M 6 may, for example, be a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• Each of R 1 and R 2 may, for example, be a hydrogen atom, alkyl which may be substituted by M 7 , alkenyl which may be substituted by M 7 , alkynyl- which may be substituted by M 7 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• R 3 may, for example, be alkyl which may be substituted by M 7 , alkenyl which may be substituted by M 7 , alkynyl which may be substituted by M 7 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• the number of substituents M 7 may be one or more, and if more, they may be the same or different.
• M 1 is as defined above.
• Each of M 8 and M 9 may, for example, be a hydrogen atom, alkyl which may be substituted by M 1 , alkenyl which may be substituted by M 1 , alkynyl which may be substituted by M 1 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• M 10 may, for example, be alkyl which may be substituted by M 1 , alkenyl which may be substituted by M 1 , alkynyl which may be substituted by M 1 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• V may, for example, be a hydrogen atom, alkyl which may be substituted by M 1 , alkenyl which may be substituted by M 1 , alkynyl which may be substituted by M 1 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• M 1 is as defined above.
• R 4 and R 5 may, for example, be a hydrogen atom, alkyl, haloalkyl, arylalkyl, heteroarylalkyl , cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl .
• R 6 may, for example, be alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl.
• each atom of fluorine, chlorine, bromine or iodine may be mentioned.
• the number of halogens as substituents may be 1 or more, and if more, the respective halogens may be the same -or different. Further, the positions for substitution of halogens may be any positions.
• the alkyl or alkyl moiety may be linear or branched, and as its specific example, C ⁇ _ ⁇ 2 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl may be mentioned.
• C ⁇ _ ⁇ 2 alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl may be mentioned.
• alkenyl or alkenyl moiety may be linear or branched, and as its specific example, C_ 12 alkenyl such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3- butadienyl, 1-hexenyl, 1-heptenyl, 4-octenyl, 2-decenyl or 2-dodecenyl may be mentioned.
• C_ 12 alkenyl such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3- butadienyl, 1-hexenyl, 1-heptenyl, 4-octenyl, 2-decenyl or 2-dodecenyl may be mentioned.
• the alkynyl or alkynyl moiety may be linear or branched, and as its specific example, C 2 _i 2 alkynyl such as ethynyl, 2-butynyl, 2-pentynyl, 3-hexynyl, 4,4- dimethyl-2-pentynyl, 4-octynyl, 2-decynyl or 2-dodecynyl may be mentioned.
• the cyclic hydrocarbon group may be either a monocyclic type or a condensed polycyclic type and may be saturated or may have an unsaturated moiety.
• a specific Example -of the monocyclic hydrocarbon group may, for example, be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl , cyclooctenyl, cyclohexadienyl, . cyclooctadienyl, cyclooctynyl or phenyl.
• a specific example of the condensed polycyclic hydrocarbon group may, for example, be naphthyl, anthryl, phenanthryl , indenyl or indanyl .
• heterocyclic group containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom a monocyclic or condensed ring type heterocyclic group containing from 1 to 4 hetero atoms, may, for example, be mentioned.
• a heterocyclic group may be saturated or may have an unsaturated moiety, or its methylene moiety may be converted to oxo or thioxo, or may be an N-oxide such as N-oxypyridyl .
• it may, for example, be 1) a heterocyclic group selected from the group consisting of thienyl, furyl, pyrrolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, triazolyl, tetrazolyl, dithiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, oxazinyl, thiazinyl, pyranyl, benzothienyl, benzofuranyl, indolyl, isoindolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, benzimidazolyl, indazolyl, cyclopentapyrazolyl, benzothi
• the triazolyl includes 1, 2 , 3-triazolyl and 1, 2 , 4-triazolyl; the triazinyl includes, 1, 2 , 4-triazinyl and 1, 3 , 5-triazinyl ;
• the benzothienyl includes benzo [b] thienyl and benzo [c] thienyl;
• the benzofuranyl includes benzo [b] furanyl and benzo [c] furanyl;
• the benzisothiazolyl includes 1, 2-benzisothiazolyl and 2 , 1-benzisothiazolyl;
• the benzisoxazolyl includes 1, 2-benzisoxazolyl and 2,1- benzisoxazolyl; and
• the benzothiadiazolyl includes 1,2,3- benzothiadiazolyl and 2 , 1, 3-benzothiadiazolyl .
• the above-mentioned partially saturated heterocyclic group may be one having a part of the above heterocyclic group hydrogenated.
• the above-mentioned saturated heterocyclic group may be one having the above heterocyclic group completely hydrogenated.
• oxo or thioxo heterocyclic group may be one having a methylene moiety in the above- mentioned dithiazolyl, oxadinyl, thiadinyl, pyranyl, cyclopentapyrazolyl, benzodioxolyl, partially saturated heterocyclic group or saturated heterocyclic group, converted to oxo or thioxo.
• cycloalkyl or cycloalkyl moiety C 3 . 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cyclooctyl may be mentioned.
• aryl or aryl moiety phenyl, naphthyl, anthryl, phenanthryl, indenyl or indanyl may be mentioned.
• heteroaryl or heteroaryl moiety the same one as the above-mentioned heterocyclic group may be mentioned.
• the salt of the haloalkene compound of the above formula (I) includes all kinds so long as they are agriculturally acceptable.
• an alkali metal salt such as a sodium salt or a potassium salt
• an alkaline earth metal salt such as a magnesium salt or a calcium salt
• an ammonium salt such as a dimethylamine salt or a triethylamine salt
• an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate
• an organic acid salt such as an acetate or a methanesulfonate
• the haloalkene compound of the formula (I) may have geometrical isomers, optical isomers or tautomeric isomers, and such isomers and mixtures thereof are both included in the present invention.
• haloalkene compound of the formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) can be produced by the following reactions (A) to (H) and in accordance with a usual method for producing a sal .
• X 1 , X 2 , Y, n, L, G and A are as defined above.
• a salt of the compound of the formula (III) a salt with an organic or inorganic acid, such as a hydrochloride, a sulfate, an oxalate or a methanesulfonate, may be mentioned.
• the reaction (A) can be carried out in the presence of a base, as the case requires.
• one or more types may suitably be selected for use from, for example, a tertiary amine such as trimethylamine, triethylamine, triisopropylamine, diisopropylethyla ine, pyridine, 4-dimethylaminopyridine, 2 , 6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N,N- dimethylaniline, N,N-diethylaniline, N-ethyl-N- methylaniline, 1, 8-diazabicyclo [5.4.0] -7-undecene or 1,4- diazabicyclo [2.2.2] octane; an alkali metal such as sodium or potassium; an alkali metal carbonate such as sodium carbonate or potassium carbonate; an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkali metal hydride such as sodium hydride or potassium hydride; an alkali metal bicarbonate such as
• the base may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2.5 times by. mol, to the compound of the formula (II) .
• the reaction (A) can be carried out in the presence of a solvent, as the case requires.
• the solvent may be any solvent so long as it is a solvent inert to the reaction, and one or more types may suitably be selected for use from, for example, an aliphatic hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane; an aromatic hydrocarbon such as benzene, toluene, xylene or pyridine; a halogenated hydrocarbon such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dich ' loroethane or trichloroethane; an ether such as diethyl ether, butyl ethyl ether, tetrahydrofuran, dioxane, dimethoxyethane or anisole; an ester such as methyl acetate, ethyl acetate or propyl acetate; a ketone such as acetone, die
• the reaction (A) can be carried out in an atmosphere of an inert gas, as the case requires.
• an inert gas each gas such as nitrogen, helium or argon may be mentioned.
• the reaction (A) can be carried out usually at a temperature of from -78 to +250°C, preferably from -78 to +150°C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours.
• reaction (B) X 1 , X 2 , Y, n, L, G and A are as defined above, T is an oxygen atom or a sulfur atom.
• T is an oxygen atom or a sulfur atom.
• the salt of the compound represented by the formula (III) the same one as exemplified in the above- mentioned reaction (A) may be mentioned.
• the reaction (B) can be carried out by azeotropic dehydration in the presence of a solvent or in the presence of a condensing agent.
• the solvent to be used for the azeotropic dehydration may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from those exemplified in the above-mentioned reaction (A) .
• a solvent may be used as the case requires .
• the solvent to be used here may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from those exemplified in the above reaction (A) .
• a carbodiimide such as 1, 3-dicyclohexylcarbodiimide, 1, 3-diisopropylcarbodiimide or l-ethyl-3- (3- dimethylaminopropyl) carbodiimide hydrochloride; or others such as phenyl dichlorophosphate, diethyl cyanophosphonate, 1,3 ' , 5-triaza-2 , 4 , 6-triphosphorin- 2 , 2 , 4, 4, 6, 6-hexachloride, cyanuric chloride, isobutyl chloroformate, chlorosulfonyl isocyanate, N,N' -carbonyl diimidazole, or trifluoroacetic anhydride, may be mentioned.
• the condensing agent may be used in an amount of from 1 to 5 times by mol, preferably from 1 to 2 times by mol, to the compound of the formula (IV) .
• the reaction (B) can be carried out in the presence of a base, as the case requires.
• one or more types may suitably be selected for use from, for example, tertiary amines such as trimethylamine, triethylamine, triisopropyla ine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2 , 6-dimethylpyridine, 4-pyrrolidinopyridine, N-methylmorpholine, N,N- dimethylaniline, N,N-diethylaniline, and N-ethyl-N- ethylaniline.
• the base may be used in an amount of from 0.1 to 5 times by mol, preferably from 0.1 to 2.5 times by mol, to the compound of the formula (IV) .
• the reaction (B) can be carried out in an atmosphere of an inert gas, as the case requires.
• an inert gas one such as nitrogen, helium or argon may be mentioned.
• the reaction (B) can be carried out usually at a temperature of from -78 to +250°C, preferably from 0 to 150°C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours.
• reaction (I) In the reaction (C) , X 1 , X 2 , Y, n, L, G, A and T are as. defined above, and Z is C ⁇ _ 4 alkyl. Further, as the salt of the compound represented by the formula (III) , the same one as exemplified in the above reaction (A) may, for example, be mentioned.
• the reaction (C) can be carried out in the presence of a base, as the case requires.
• one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A) , and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium butoxide; and tertiary amines such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2 , 6-dimethylpyridine, 4-pyrrolidinopyridine, N- methylmorpholine, N,N-dimethylaniline, N,N-diethylaniline, and N-ethyl-N-methylaniline.
• alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium butoxide
• tertiary amines such as trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine,
• the base may be used in an amount of from 0.01 to 5 times. by mol, preferably from 0.01 to 2.5 times by mol, to the compound of the formula (V) .
• the reaction (C) can be carried out in the presence of a solvent, as the case requires.
• the solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A) .
• the reaction (C) can be carried out in an atmosphere of an inert gas, as the case requires.
• the inert gas each gas such as nitrogen, helium or argon may be mentioned.
• the reaction (C) can be carried out usually at a temperature of from -78 to +250°C, preferably from 0 to 150°C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours.
• the reaction (D) can be carried out in the presence of a base, as the case requires.
• a base one or • more types may suitably be selected for use from, for example, those exemplified in the above reaction (A) .
• the base may be used in an amount of from 0.01 to 10 times by mol, preferably from 0.01 to 5 times by mol, to the compound of the formula (1-1) .
• the reaction (D) can be carried out in the presence of an N-trialkylsilyl-alkylcarbamate, as the case requires.
• N-trialkylsilyl-alkylcarbamate one or more types may suitably be selected for use from, for example, N-trimethylsilyl-ethylcarbamate and N- triethylsilyl-methylcarbamate.
• the N-trialkylsilyl- alkylcarbamate may be used in an amount of from 0.01 to 10 times by mol, preferably from 0.01 to 5 times by mol, to the compound of the formula (1-1) .
• the reaction (D) can be carried out in the presence of a solvent, as the case requires.
• the solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, those exemplified in the above-mentioned reaction (A) .
• the reaction (D) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert gas, one such as nitrogen, helium or argon may be mentioned.
• the reaction (D) can be carried out usually at a temperature of from -78 to +250°C, preferably from 0 to 150°C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours.
• reaction (E) X 1 , X 2 , Y, n, L and A are as defined above, G 2 is alkyl, and U is alkyl, haloalkyl, alkoxy, phenyl, phenyl substituted by halogen, or phenyl substituted by alkyl.
• the reaction (E) can be carried out in the presence of a base, as the case requires.
• the base one or more types may suitably be selected for use from, for example, those exemplified in the above reaction (A) .
• the base may be used in an amount of from 0.01 to 10 times by mol, preferably from 0.01 to 5 times by mol, to the compound of the formula (1-1) .
• the reaction (E) can be carried out in the presence of a solvent, as the case requires.
• the solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, those exemplified in the above-mentioned reaction (A) .
• the reaction (E) can be carried out in an atmosphere of an inert gas, as the case requires. As such an inert gas, each gas such as nitrogen, helium or argon may be mentioned.
• the reaction (E) can be carried out usually at a temperature of from -78 to +250°C, preferably from 0 to 150°C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours. [F]
• X 1 , X 2 , Y, n, L and G are as defined above.
• a carbonyl moiety in a case where a carbonyl moiety is present in L, such a carbonyl moiety can be thionized.
• phosphorus pentasulfide or Lawesson's reagent may, for example, be mentioned.
• the thionizing agent may be used in an amount of from 1 to 10 times by mol, preferably from 1 to 4 times by mol, to the compound of the formula (1-4) .
• the reaction (F) can be carried out in the presence of a solvent, as the case requires.
• the solvent may be any solvent so long as it is a solvent inert to the reaction, and for example, one or more types may suitably be selected for use from, for example, aliphatic hydrocarbons such as pentane, hexane, heptane, octane and cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene and pyridine; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane and trichloroethane; ethers such as diethyl ether, butyl ethyl ether, tetrahydrofur
• the reaction (F) can be carried out in an atmosphere of an inert gas, as the case requires.
• an inert gas each gas such as nitrogen, helium or argon may be mentioned.
• the reaction (F) can be carried out usually at a temperature of from -78 to +250°C, preferably from 0 to 150°C, and the reaction time is usually from 0.1 to 72 hours, preferably from 0.1 to 24 hours.
• the salt of the compound of the formula (VIII) the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.
• the reaction (G) can be carried out in the same manner as the above reaction (A) .
• reaction (I-7) In the reaction (H) , X 1 , X 2 , Y, n, G, A, B and Q are as defined above. Further, as the salt of the compound • of the formula (VIII) , the same one as the salt of the compound of the above formula (III) may, for example, be mentioned.
• the reaction (H) can be carried out in the same manner as the above reaction (A) .
• Each starting materials of the formula (II) , (IV) or (V) in the above reaction (A) to (C) is (1) a known compound, or (2) can be produced by or in accordance with the Preparation Examples given hereinafter, or (3) can be produced by or in accordance with the method disclosed in W092/15555, EP661289 or EP432861. The above (3) will be described in more detail.
• the agricultural and horticultural pesticides containing the compounds of the present invention are useful as an insecticide, a miticide, a nematicide and a soil pesticide, and they are effective for controlling plant parasitic mites such as two-spotted spider mite (Tetranychus urticae) , carmine spider mite (Tetranychus cinnabarinus) , kanzawa spider mite (Tetranychus kanzawai ) , citrus red mite (Panonychus citri) , European red mite (Panonychus ul i) , broad mite (Polyphagotarsonemus latus) , pink citrus rust mite (Aculops pelekassi) and bulb mite (Rhizoglyphus echinopus) ; aphids such as green peach aphi
• the agricultural and horticultural pesticides containing the compounds of the present invention are particularly effective for controlling plant parasitic mites, agricultural insect pests, plant parasitic nematodes or the like. Further, they are effective against insect pests having acquired resistance to organophosphorus, carbamate and/or synthetic pyrethroid insecticides.
• the compounds of the present invention have excellent systemic properties, and by the application of the compounds of the present invention to soil treatment, not only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.
• Another preferred embodiments of the pesticides containing compounds of the present invention may be agricultural and horticultural pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests.
• the agricultural and horticultural pesticide containing the compound of the present invention is usually formulated by mixing the compound with various agricultural adjuvants and used in the form of a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension concentrate, water soluble granules, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol or an ultra low-volume formulation.
• a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension concentrate, water soluble granules, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol or an ultra low-volume formulation.
• a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water
• Such agricultural adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethylsulfoxide, N,N- dimethylformamide, dimethyl cetamide, N-methyl-2- pyrrolidone, and alcohol; ' anionic surfactants and spreaders such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric acid ester,
• each of the components as such adjuvants may be one or more suitably selected for use, so long as the purpose of the present invention can thereby be accomplished.
• various additives which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, and an anti-mold agent, may also be employed.
• the weight ratio of the compound of the present invention to the various agricultural adjuvants is usually from 0.001:99.999 to 95:5, preferably from 0.005:99.995 to 90:10.
• the agricultural and horticultural pesticide containing the compound of the present invention can not generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects.
• the active ingredient being from 0.05 to 800,000 ppm, preferably from 0.5 to 500,000 ppm, and the dose per unit area is such that the compound of the present invention is from 0.05 to 50,000 g, preferably from 1 to 30,000 g, per hectare.
• agricultural and horticultural pesticides as another preferred embodiment of pesticides containing the compounds of the present invention may be applied in accordance with the above-described application of pesticides.
• the present invention includes such a method for controlling pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes by such applications.
• compositions of agricultural and horticultural pesticides containing the compounds of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e.g. spraying, jetting, misting, atomizing, powder or grain scattering or dispersing in water) , soil application (e.g. mixing or drenching) , surface application (e.g. coating, powdering or covering) or impregnation to obtain poisonous feed.
• spraying e.g. spraying, jetting, misting, atomizing, powder or grain scattering or dispersing in water
• soil application e.g. mixing or drenching
• surface application e.g. coating, powdering or covering
• impregnation to obtain poisonous feed.
• the active ingredient may also be applied by a so-called ultra low-volume application method
• the composition may be composed of 100% of the active ingredient .
• the agricultural and horticultural pesticides containing compounds of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained.
• Such other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone and a plant growth regulating agent.
• a mixed pesticide having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals the application range, the application time, the pesticidal activities, etc.
• the compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together.
• the present invention includes such a mixed pesticidal composition.
• the mixing ratio of the compound of the present invention to the active compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc., but it is usually within a range of from 1:300 to 300:1, preferably from 1:100 to 100:1, by weight.
• the dose for the application is such that the total amount of the active compounds is from 0.1 to 50,000 g, preferably from 1 to 30,000 g, per hectare.
• the present invention includes a method for controlling pests by an application of such a mixed pesticide composition.
• the active compounds of insect pest control agents such as insecticides, miticides, nematicides or soil pesticides in the above-mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage) organic phosphate compounds such as Profenofos, Dichlorvos, Fenamiphos, Fenitrothion, EPN, Diazinon, Chlorpyrifos- methyl, Acephate, Prothiofos, Fosthiazate, Phosphocarb, Cadusafos, Disulfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, and Methamidophos ; carbamate compounds such as Carbaryl, Propoxur, Aldicarb, Carbofuran, Thiodicarb, Metho yl, Oxamyl, Ethiofencarb, Pirimicarb, Fenobucarb, Carbosulfan, and Benfuracarb; nereist
• BT agents microbial agricultural chemicals such as insect viruses, entomopathogenic fungi, and nematophagous fungi, or antibiotics such as Avermectin, Emamectin-Benzoate, Milbemectin, Spinosad, and Ivermectin, may be used in admixture or in combination.
• the active compounds of fungicides among the above- mentioned other agricultural chemicals include, for example, (by common names, some of which are still in an application stage) pyrimidinamine compounds such as Mepanipyrim, Pyrimethanil, and Cyprodinil; azole compounds such as Triadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Flusilazole, Myclobutanil, Cyproconazole, Terbuconazole, Hexaconazole, Furconazole-cis, Prochloraz, Metconazole, Epoxiconazole, Tetraconazole, Oxpoconazole, and Sipconazole; quinoxaline compounds such as Qtiinomethionate; dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarbamate, Propineb; organic chlorine compounds such as Fthalide, Chlorothalonil, and Quintozene; imidazole compounds
• Cyazofamid pyridinamine compounds such as Fluazinam; cyanoacetamide compounds such as Cymoxanil; phenylamide compounds such as Metalaxyl, Oxadixyl, Ofurace, Benalaxyl, Furalaxyl, and Cyprofuram; sulfenic acid compounds such as Dichlofluanid; copper compounds such as cupric hydroxide, and Oxine Copper; isoxazole compounds such as Hydroxyisoxazole; organophosphorus compounds such as Fosetyl-Al, Tolclofos-Methyl, S-benzyl 0,0- diisopropylphosphorothioate, 0-ethyl S,S- diphenylphosphorodithioate, and aluminumethylhydrogen phosphonate; N-halogenothioalkyl compounds such as Captan, Captafol, and Folpet; dicarboximide compounds such as Procy idone, Ipro
• Strobilurin compounds such as Azoxystrobin, Kresoxim-Methyl , Metominofen, Trifloxystrobin, Picoxystrobin, and Pyraclostrobin; oxazolidinone compounds such as Fa oxadone; thiazole carboxamide compounds such as Ethaboxa ; silyl amide compounds such as Silthiopham; aminoacid amidecarbamate compounds such as Iprovalicarb; imidazolidine compound such as Fenamidone; hydroxyanilide compounds such as Fenhexainid; benzene sulfonamide compounds such as Flusulfamide; anthraquinone compounds; crotonic acid compounds; antibiotics; and other compounds, such as Isoprothiolane, Tricyclazole, Pyroquilon, Diclomezine, Probenazole, Quinoxyfen, Propamocarb Hydrochloride, Spiroxamine
• agricultural chemicals which may be used in admixture with or in combination with the compounds of the present invention, may, for example, be the active ingredient compounds in the herbicides as disclosed in Farm Chemicals Handbook (2000 edition) , particularly those of soil treatment type.
• the pesticides against parasites on animals are effective for controlling e.g. external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh) or internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues) , but they are particularly effective for controlling the external parasites .
• the external parasites may, for example, be animal parasitic acarus or fleas. Their species are so many that it is difficult to list all of them, and therefore, their typical examples will be given.
• the animal parasitic acarus may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus , Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, Haemaphysa1is concinna, Haemaphysalis japonica, Hae aphysa1is kitaokai, Haemaphysa1is ias, Ixodes ovatus, Ixodes nipponensis, Ixodes persulcatus, Ablyomma testudinariu , Haeroaph sa1is ipegaspinosa, Dermacentor reticulatus, and Dermacentor
• the pesticides against parasites on animals, containing the compounds of the present invention are particularly effective for the control of ticks among them.
• the fleas may, for example, be externally parasitic wingless insects belonging to Siphona tera, more specifically, fleas belonging to Pulicidae, Ceratephyllus , etc.
• Fleas belonging to Pulicidae may for example, be Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaga gallinacea, Xenopsylla cheopis , Leptopsylla segnis, Nosopsyllus fasciatus, and
• Monopsyllus anisus The pesticides against parasites on animals, containing the compounds of the present invention, are particularly effective for the control of fleas belonging to Pulicidae, particularly Ctenocephalides canis and Ctenocephalides felis, among the .
• Other external parasites may, for example, be sucking lice (Anoplura) such as shortnosed cattle louse (Haematopinus eurysternus) , horse sucking louse (Haematopinus asini) , sheep louse, longnosed cattle louse (Linognathus vituli) , and head louse (Pediculus capitis) ; biting lice such as dog biting louse (Trichodectes canis) ; and blood-sucking dipterous insects such as horsefly (Tabanus trigonus) , biting midges (Culicoides schultzei) , and blackfly (Simulium ornaturn) .
• the internal parasites may, for example, be nematodes such as lung worms, whipworms (Trichuris) , tuberous worms, gastric parasites, ascaris, and filarioidea; tapeworms; flukes; and protozoa such as coccidia, malaria parasites (Plasmodiu malariae) , intestinal sarcocyst, toxoplasma, and cryptosporidium.
• nematodes such as lung worms, whipworms (Trichuris) , tuberous worms, gastric parasites, ascaris, and filarioidea
• tapeworms such as coccidia, malaria parasites (Plasmodiu malariae) , intestinal sarcocyst, toxoplasma, and cryptosporidium.
• the host animals may, for example, be pet animals such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries) ; domestic animals such as cows, horses, pigs and sheep; and poultry such as ducks and chickens.
• pet animals such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries) ; domestic animals such as cows, horses, pigs and sheep; and poultry such as ducks and chickens.
• the pesticides against parasites on animals, containing the compounds of the present invention are particularly effective for the control of pests parasitic on pet animals or domestic animals, especially for the control
• the compound of the present invention when used as a pesticide against parasites on animals, it may be used as it is or may be used together with suitable adjuvants, as formulated into various formulations such as a dust, granules, tablets, a powder, capsules, a soluble concentrate, an emulsifiable concentrate, a water-based suspension concentrate and an oil-based suspension concentrate. In addition to such formulations, it may be formulated into any type of formulation which is commonly used in this field, so long as it is suitable for the purpose of the present invention.
• the adjuvants to be used for formulations may, for example, be anionic surfactants or nonionic surfactants exemplified above as adjuvants for formulation of agricultural and horticultural pesticides; a cationic surfactant such as cetyl trimethylammonium bromide; a solvent such as water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylforma ide, 2-pyrrolidone, N- methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n- butyl ether, dipropylene glycol monomethyl ether, or dipropylene
• One or more of the respective components of these adjuvants may be suitably selected for use, so long as such will not depart from the purpose of the present invention. Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use, and still further, some among the above- mentioned various adjuvants to be used in the agricultural and horticultural field may suitably be selected for use.
• the blend ratio of the compound of the present invention to various adjuvants is usually from 0.1:99.9 to 90:10. In the actual use of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders (e.g.
• ком ⁇ онент of the present invention may be added thereto, as the case requires .
• Administration of the compound of the present invention to a host animal is carried out orally -or parenterally.
• an oral administration method a method of administering a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat or other feed, containing the compound of the present invention, may be mentioned.
• a parenteral administration method there may, for example, be mentioned a method wherein the compound of the present invention is formulated into a suitable formulation and then taken into the body by e.g.
• intravenous administration intramuscular administration, intradermal administration, hypodermic administration, etc.; a method wherein it is administered on the body surface by spot-on treatment, pour-on treatment or spray treatment; or a method of embedding a resin fragment or the like containing the compound of the present invention under the skin of the host animal.
• the dose of the compound of the present invention to a host animal varies depending upon the administration method, the purpose of administration, the deceased symptom, etc . , but it is usually administered in a proportion of from 0.01 mg to 100 g, preferably from 0.1 mg to 10 g, per 1 kg of the body weight of the host animal .
• the present invention also includes a method for controlling a pest by the above-mentioned administration method or by the above-mentioned dose, particularly a method for controlling external parasites or internal parasites .
• a method for controlling a pest by the above-mentioned administration method or by the above-mentioned dose particularly a method for controlling external parasites or internal parasites .
• various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sedatives, antiphlogistics, fungicides, colorants, aromatic substances, preservatives, etc. may be used in admixture with or in combination with the adjuvants.
• the present invention includes such a mixed pesticidal composition having the above- mentioned various components mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites.
• a method for controlling a pest by using it particularly a method for controlling external parasites or internal parasites.
• Q is alkyl which may be substituted by W, alkenyl which may be substituted by W, alkynyl which may be substituted by W, a cyclic hydrocarbon group which may be substituted by W, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by W) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom;
• each of M 2 and M 3 is a hydrogen atom, alkyl which may be substituted by M 5 , alkenyl which may be substituted by M 5 , alkynyl which may be substituted by M 5 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom;
• M 4 is alkyl which may be substituted by M 5 , alkenyl which may be substituted by M 5 , alkynyl which may be substituted by M 5 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom;
• M 5 is halogen, alkoxy which may be substituted by .
• M 1 alkylthio which may be substituted by M 1 , alkylsulfinyl which may be substituted by M 1 , alkylsulfonyl which may be substituted by M 1 , -M 6 , -OM 6 or -SM 6 ;
• M 6 is a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom;
• each of R 1 and R 2 is a hydrogen atom, alkyl which may be substituted by M 7 , alkenyl which may be substituted by M 7 , alkynyl which may be substituted by M 7 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- _ to 12-member
• R 3 is alkyl which may be substituted by M 7 , alkenyl which may be substituted by M 7 , alkynyl which may be substituted by M 7 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; M 7 is halogen, a cyclic hydrocarbon group which may be substituted by M 1 , a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, -OM 8 , -SM 8 , -NM 8 M 9 , -COM 8 , -C0 2 M 8 , -COSM 8 , -CSOM 8 , -CS 2 M 8 , -
• each of M 8 and M 9 is a hydrogen atom, alkyl which may be substituted by M 1 , alkenyl which may be substituted by M 1 , alkynyl which may be substituted by M 1 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom;
• M 10 is alkyl which may be substituted by M 1 , alkenyl which may be substituted by M 1 , alkynyl which may be substituted by M 1 , a cyclic hydrocarbon group which may be substituted by M 1 , or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by M 1 ) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom; V is a hydrogen atom, alkyl which may be substituted by M 1 , alkenyl which may be substituted by M 1 , alkynyl which may be substituted by M 1 , a cyclic hydrocarbon group which may be .
• each of R 4 and R 5 is a hydrogen atom, alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl ;
• R 6 is alkyl, haloalkyl, arylalkyl, heteroarylalkyl, cycloalkyl, halocycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl or heteroaryl.
• Q is a cyclic hydrocarbon group which may be substituted by W, or a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted by W) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom.
• Q is a cyclic hydrocarbon group which may be substituted by W.
• each of X 1 and X 2 is halogen; Y is alkyl, haloalkyl or phenyl; n is from 0 to 5; each of A and B is an oxygen atom or a sulfur atom; G is a hydrogen atom, alkyl, haloalkyl, phenylalkyl, alkenyl, haloalkenyl, phenylalkenyl, alkynyl, haloalkynyl or phenylalkynyl; Q is a 5- to 12-membered heterocyclic group (the heterocyclic group may be substituted) containing an optional hetero atom selected from an oxygen atom, a sulfur atom and a nitrogen atom, alkyl which may be substituted by W, alkenyl which may be substituted by W, alkynyl which may be substituted by W, or a cyclic hydrocarbon group which may be substituted by W; W is halogen, alkyl, haloalkyl
• the organic layer was washed with 100 ml of water and washed three times with 50 ml of a saturated sodium chloride aqueous solution.
• the aqueous layer was extracted with 200 ml of ethyl ether, followed by washing five times with 50 ml of a saturated sodium chloride aqueous solution.
• the obtained all organic layers were dried over anhydrous sodium sulfate, and ethyl ether was distilled off under reduced pressure to obtain 243.82 g of oily crude ethyl 7- oxononanoate ' .
• the organic layer was washed once with 930 ml of water and five times with 400 ml of water and thereafter washed once with 100 ml of a saturated sodium chloride aqueous solution, to obtain 149.6 g of oily crude ethyl 7-ethyl-8 , 8-difluoro-7-octenoate.
• a mixed solution comprising 50.64 g of 85% potassium hydroxide and 550 ml of methanol, was added to 149.6 g of the crude ethyl 7-ethyl-8, 8-difluoro-7-octenoate, and the mixture was reacted at room temperature for 3 days .
• a mixed solution comprising the above crude 7-ethyl-8,8- difluoro-7-octenoyl chloride and 10 ml of tetrahydrofuran, was dropwise added thereto, and the mixture was reacted for 20 minutes. Then, the mixture was returned to room temperature and further reacted for 5 hours and 30 minutes . After completion of the reaction, the reaction mixture was put into a small amount of water and then into a saturated sodium chloride aqueous solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure.
• reaction mixture was put into water and extracted with ethyl acetate .
• the organic layer was dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure.
• PREPARATION EXAMPLE 6 Preparation of 2 ' -benzhydrylidene 7-ethyl-8, 8-difluoro-7- octenohydrazide (after-mentioned Compound No. 2-8) A mixture comprising 0.206 g of crude 7-ethyl-8,8- difluoro-7-octenoic acid, 0.196 g of benzophenone hydrazone, 0.2 g of l-ethyl-3- (3- dimethylammopropyl) carbodiimide hydrochloride and 3 ml of dichloromethane, was reacted at room temperature for
• Me represents a methyl group
• Et an ethyl group n-Pr a n-propyl group
• i-Pr an isopropyl group
• t-Bu a tert-butyl group
• n-Oct a n-octyl group n-Dode a n-dodecyl group
• Ph a phenyl group.
• Ph(2-Cl) represents a phenyl group having a chlorine atom substituted at the 2- position
• Ph(4-Ph(4-CF 3 ) ) a phenyl group having a phenyl group (this phenyl group has a CF 3 group substituted at the 4-position) substituted at the 4-position
• Ph(4- 0-2-pyridyl (5-CF 3 ) ) a phenyl group having a 2-pyridyloxy group (this pyridyl group has a CF 3 group substituted at the 5-position) substituted at the 4-position.
• Ph(2-Cl) represents a phenyl group having a chlorine atom substituted at the 2- position
• Ph(4-Ph(4-CF 3 ) a phenyl group having a phenyl group having a phenyl group (this phenyl group has a CF 3 group substituted at the 4-position) substituted at the 4-position
• TEST EXAMPLE 1 Test on southern root-knot nematode (Meloidogyne incognita)
• 10 ml of a chemical solution having the concentration of the compound of the present invention adjusted to be 800 ppm was poured, followed by mixing so that the compound was uniformly dispersed.
• the treated soil was put into a pot (diameter: 8 cm, height: 9 cm), and then a tomato seedling in 2-leaf stage was transplanted and placed in a greenhouse.
• the root knot index was determined based on the following standards of Table 4. Such determination was made with respect to the above-mentioned Compound Nos. 1-51, 2-1, 2-3, 2-4, 2-6 and 2-9, whereby all compounds showed high controlling effects at a level of a root knot index of not more than 1.
• TEST EXAMPLE 4 Pesticidal test against New Zealand cattle mite (Haemaphysalis longicornis)
• a Petri dish having a diameter of 9 cm 1 ml of an acetone solution of the compound of the present invention (concentration: 10 ⁇ g/ml) is dropped by a micropipette.
• the internal surface of the Petri dish dries up, from 60 to 180 infant mites are put, and the Petri dish is covered with a polyethylene sheet and sealed by an elastic band.
• the number of knocked down mites after contact with the pesticide is observed, whereby the compound of the present invention knocks down the majority of New Zealand cattle mite.
• Pesticidal test against New Zealand cattle mite (Haemaphysa1is longicornis) , employing a dog 50 Young mites of New Zealand cattle mite are released on the auricle of a dog (beagle, 8 months old) and artificially parasitized. Upon expiration of two days from parasitizing, the number of parasitized mites is counted, and then the compound of the present invention formulated is spotted on at a dose of 10 mg/kg at the dorsal cervical region. Up to five days after administration of the pesticide, observation is carried out to insect the parasitic number, the fallen number and the mortality of the fallen New Zealand cattle mite.
• the dog is individually raised in a cage and permitted to drink tap water freely, and a predetermined amount of a dog food is given once a day.
• the compound of the present invention is effective to have the parasitized New Zealand cattle mite fallen or dead.
• Pesticidal test against cat flea employing a dog 100 non-bloodsucked adults of cat flea (Ctenocephalides felis) within three days after adult emergence are released on the dorsal fur of a dog (beagle, 8 months old) and artificially parasitized, and the compound of the present invention formulated is spotted on at a dose of 10 mg/kg on the dorsal cervical region.
• the cat flea is recovered by means of a flea catching comb, and the parasitized number is counted.
• the dog is individually raised in a cage and permitted to drink tap water freely, and a predetermined amount of a dog food is given once a day.
• the compound of the present invention is effective to control the parasitizing of cat flea.
• FORMULATION EXAMPLE 1 (1) Compound of the present invention 20 parts by weight (2) Clay 72 parts by weight (3) Sodium lignin sulfonate 8 parts by weight The above components are uniformly mixed to obtain a wettable powder .
• FORMULATION EXAMPLE 2 (1) Compound of the present invention 5 parts by weight (2) Talc 95 parts by weight The above components are uniformly mixed to obtain a dust.
• FORMULATION EXAMPLE 3 (1) Compound of the present invention 20 parts by weight (2) N,N'-dimethylacetamide 20 parts by weight (3) Polyoxyethylenealkylphenyl ether 10 parts by weight (4) Xylene 50 parts by weight The above components are uniformly mixed and dissolved to obtain an emulsifiable concentrate.
• FORMULATION EXAMPLE 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylenealkylaryl sulfate 5 parts by weight (4) Fine silica powder 25 parts by weight A mixture of the above components is mixed with compound of the present invention in a weight ratio of 4:1 to obtain a wettable powder .
• FORMULATION EXAMPLE 5 (1) Compound of the present invention 50 parts by weight (2) Oxylated polyalkylphenyl phosphate-triethanolamine 2 parts by weight (3) Silicone 0.2 part by weight (4) Water 47.8 parts by weight The above components are uniformly mixed and pulverized to obtain a base liquid, and (5) Sodium polycarboxylate 5 parts by weight (6) Anhydrous sodium sulfate 42.8 parts by weight are added, and the mixture is uniformly mixed and dried to obtain water-dispersible granules .
• FORMULATION EXAMPLE 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethyleneoctylphenyl ether 1 part by weight (3) polyoxyethylene phosphoric acid ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight The above components (1) to (3) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (4), and acetone is removed to obtain granules.
• FORMULATION EXAMPLE 7 (1) Compound of the present invention 2.5 parts by weight (2) N-methyl-2-pyrrolidone 2.5 parts by weight (3) Soybean oil 95.0 parts by weight The above components are uniformly mixed and dissolved to obtain an ultra low volume formulation.
• FORMULATION EXAMPLE 8 (1) Compound of the present invention 40 parts by weight (2) Oxylated polyalkylphenylphosphate- triethanolamine 2 parts by weight (3) Silicone 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 parts by weight (6) Water 52.7 parts by weight The above components are uniformly mixed and pulverized to obtain a water-based suspension concentrate.
• FORMULATION EXAMPLE 9 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 90 parts by weight The above components are uniformly mixed to obtain a soluble concentrate.

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