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WO2007125984A1 - Derive isoxazoline, agent insecticide et utilisation de l'agent insecticide - Google Patents

Derive isoxazoline, agent insecticide et utilisation de l'agent insecticide Download PDF

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Publication number
WO2007125984A1
WO2007125984A1 PCT/JP2007/059040 JP2007059040W WO2007125984A1 WO 2007125984 A1 WO2007125984 A1 WO 2007125984A1 JP 2007059040 W JP2007059040 W JP 2007059040W WO 2007125984 A1 WO2007125984 A1 WO 2007125984A1
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Prior art keywords
group
substituted
halo
alkyl
heterocyclic
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PCT/JP2007/059040
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English (en)
Japanese (ja)
Inventor
Hiroto Harayama
Eiji Takizawa
Masanori Tohnishi
Akiyuki Suwa
Shinsuke Fujioka
Naoki Sawada
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Nihon Nohyaku Co., Ltd.
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Priority to JP2008513251A priority Critical patent/JPWO2007125984A1/ja
Publication of WO2007125984A1 publication Critical patent/WO2007125984A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • 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
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to an isoxazoline derivative or a salt thereof, a pest control agent comprising the compound as an active ingredient, particularly an agricultural and horticultural insecticide, and a method of using the same.
  • Certain isoxazoline derivatives pesticides and (for example, see Patent Documents 1 to 3.) Is known to be particularly useful as an agricultural and horticultural insecticide 0 with teeth force, JP
  • the compounds described in 1 and 2 are compounds in which an amide or thioamide is bonded to the 4-position of the 3-position (hetero) aryl group of the isoxazoline ring, and the compound described in Patent Document 3 is the 3-position of the isoxazoline ring.
  • a compound in which a heterocycle is bonded to the 4-position of a (hetero) aryl group, and an amide or thioamide such as an oxygen atom, a sulfur atom, or a nitrogen atom is located at the 4-position of the (hetero) aryl group of the isoxazoline ring.
  • an amide or thioamide such as an oxygen atom, a sulfur atom, or a nitrogen atom
  • Patent Document 1 International Publication No. 05Z085216 Pamphlet
  • Patent Document 2 Pamphlet of International Publication No. 07Z026965
  • Patent Document 3 Japanese Patent Laid-Open No. 2007-016017
  • the present inventors have intensively studied to develop new pest control agents, particularly agricultural and horticultural insecticides.
  • the isoxazoline derivative represented by the general formula (I) of the present invention is a novel compound not described in the literature, and exhibits an excellent control effect as a pest control agent, particularly an agricultural and horticultural insecticide.
  • the present invention has been completed.
  • R 1 is a hydrogen atom; a halogen atom; a (C to C) alkyl group; a substitution substituted by Z
  • a substituted phenylamino group substituted by z a heterocyclic amine group; a substituted heterocyclic ring amino group substituted by z; a formyl group; a (c to C) alkyl carbo group; a substitution substituted by Z
  • di (C-C) alkylaminocarbol groups identical or different substituted by Z
  • a substituted mono (c-c) alkylaminosulfo group substituted by Z is same or different
  • R 2 represents a halo (C to C) alkyl group.
  • W is an oxygen atom; a sulfur atom; —SO—; — SO—; — N (R 3 ) — (wherein R 3 is a hydrogen atom;
  • a kill group a (c-c) cycloalkyl group substituted by Z; a cyano group; a formyl group;
  • a substituted heterocyclic group substituted by Z is shown.
  • R 8 and R 9 combine to form a heterocyclic ring in which the pyrrolidine ring, piperidine ring, piperazine ring, morpholine ring, thiomorpholine ring and 4-oxothiomorpholine ring are also selected.
  • the heterocycle may be substituted by Z.
  • ) Or C (SR 1C) ) (wherein R 1C) is substituted by (C-C) alkyl group or Z
  • R 4 and R 5 may be the same or different and each represents a hydrogen atom or a halogen atom).
  • a ⁇ A 2 and A 3 are the same or different nitrogen atoms; C—H; or C—Y.
  • X represents a halogen atom; a cyan group; a nitro group; a (C to C) alkyl group; a nano (C to C) alkyl
  • Y is a halogen atom; a cyan group; a nitro group; a (C to C) alkyl group; ⁇ C) alkyl group; (c ⁇ c) cycloalkyl group; (c ⁇ c) cyclo substituted by z
  • a heterocyclic oxy group a substituted heterocyclic oxy group substituted by z;
  • a substituted phenylaminocarbol group substituted by Z a heterocyclic aminocarbo group
  • a hole group a substituted (c-c) alkyl sulfonyl group substituted by z;
  • a substituted phenolsulfonyl group substituted by Z mono (c to kilamino)
  • a substituted phenol aminosulfol group substituted by z mono (c to c) An alkylamino group; a substituted mono (c-c) alkylamino group substituted by z;
  • di (c to c) alkylsulfo-lua may be the same or different
  • a -sulfamino group; a phenylsulfo-amino group; a substituted phenylsulfo-amino group substituted by Z; a heterocyclic sulfonylamino group; or a substituted heterocyclic sulfo-amino group substituted by Z; Indicates an integer of ⁇ 4.
  • Z may be the same or different halogen atom; cyan group; nitro group; (C 1 -C 6) alkyl
  • a neuro (c to c) alkyl group a cyclo (c to c) alkyl group; a nanocyclo (c to c) a
  • a ball group a mono (c-c) alkylamino group; a di (c-c) group which may be the same or different
  • Mouth (c to c) cycloalkylthio group, (c to c) alkylsulfier group, halo (c to c) ) Alkylsulfier group, (c-c) cycloalkylsulfier group, halo (c-
  • a substituted heterocyclic group having one or more substituents selected from a nyl group and a heterocyclic group; a phenoxy group; a halogen atom, a cyano group, a nitro group, which may be the same or different;
  • alkyl group halo (c-c) alkyl group, (c-c) cycloalkyl group, halo (c-
  • a substituted heterocyclic oxy group having one or more substituents selected from a heterocyclic group; a phenylthio group; a halogen atom, a cyan group, a nitro group, a (C to C) alkyl group, which may be the same or different, Halo (C-C) alkyl group, (C-C) cycloalkyl group, halo (C-
  • Phenylamino group which may be the same or different, halogen atom, cyano group, nitro group, (C-C) alkyl group, halo (C-C) alkyl group, (C-C) cycloalkyl group, halo (C ⁇
  • Phenyl group and heterocyclic group force substituted phenyl amino group having one or more selected substituents on the ring; heterocyclic amino group; halogen atom, cyano group, nitro group which may be the same or different
  • ( 4 ) W is — C (R 4 ) (R 5 ) ⁇ (wherein R 5 and R 6 are the same as (1)), or an isoxazoline derivative or a salt thereof according to (1),
  • R 2 is a fluoro (C to C) alkyl group (1) to (4)
  • X is a halogen atom or a halo (C-C 6) alkyl group (1) to (6) one force
  • a pest control agent comprising the isoxazoline derivative or a salt thereof according to any one of (1) to (7) as an active ingredient
  • J 1 is chlorine atom, bromine atom, iodine atom, (C to C 6) alkylsulfuroxy
  • Si (OEt) group —ZnCl group, ZnBr group, —Znl group, —MgCl group, —MgBr group, or Mgl
  • a pest control agent having superior performance compared to the prior art, in particular, Can provide agricultural and horticultural insecticides.
  • Halogen atom refers to a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • (C 1 -C 6) alkyl means a linear or branched alkyl having 1 to 6 carbon atoms.
  • 3 7 cycloalkyl means cyclic alkyl having 3 to 7 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the like.
  • (C 1 -C 6) alkoxy means that the alkyl moiety is the above “(C 1 -C 6) alkyl”.
  • 1 6 1 6 represents alkoxy, and examples thereof include methoxy, ethoxy, propoxy, butoxy, isobutoxy, t-butoxy, pentyloxy, hexyloxy and the like. "(C ⁇
  • “2c) al 6 kenyl” refers to a straight or branched chain alkene having 2 to 6 carbon atoms having at least one double bond, for example, bull, 1-probe. , Aryl, 1-butyr, 2 butenyl, 3 butenyl, 2 pentenyl, 2, 4 pentagenyl, 3 hexenyl and the like. “(C 1 -C 6) alkyl” has at least one triple bond
  • a linear or branched alkynyl having 2 to 6 carbon atoms is exemplified, and examples thereof include ethynyl, 2 propynyl, 1-butynyl, 2 butynyl, 3 butynyl, 2 pentynyl, 3 hexynyl and the like.
  • numbers such as “C to C” and “C to C” are 2 to 6 carbon atoms,
  • Heterocycle refers to a 5- or 6-membered heterocycle having one or more heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom, and includes, for example, pyridine, pyridine-N-oxide, Limidine, pyrazine, pyridazine, triazine, furan, tetrahydrofuran, thiophene, tetrahydrothiophene, pyrrole, pyrrolidine, pyran, tetrahydropyran, thiopyran, tetrahydrothiopyran, oxazole, oxazoline, isoxazole, isoxazoline, oxadiazole, oxadiazoline, thiazole , Thiazoline, isothiazole, isothiazoline, thiadiazole, thiadiazoline, imidazole, imidazoline, triazole, triazoline, pyrazole, pyrazoline and
  • R 1 is preferably (C to C) alkyl.
  • R 1 is preferably a (C to C) alkyl carbo group, substituted by Z
  • a rubonyl group a substituted (c-c) alkylthiocarbonyl group substituted by Z, a benzoyl group
  • R 1 is preferably substituted by a halogen atom, a (C to C) alkyl group or Z A substituted (C to C) alkyl group; Good as R 2
  • Preferred is a fluoro c to c alkyl group, and particularly preferred is a trifluoromethyl group.
  • the A ⁇ A 2 and A 3 are preferably a nitrogen atom, C—H or C—Y.
  • X is preferably a halogen atom or a halo (C to C) alkyl group, and m is preferably 1 to 3
  • Y is preferably a halogen atom, a cyano group, a nitro group, a (C to C) alkyl group, or Z.
  • Examples of the salt of the isoxazoline derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, Organic salts such as oxalate, methanesulfonate, benzenesulfonate, and paratoluenesulfonate, salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, trimethyl ammonium Can be illustrated.
  • the isoxazoline derivative represented by the general formula (I) of the present invention can be produced according to the method described in International Publication No. 05Z085216 pamphlet, for example, by the production method shown below. However, it is not limited to these.
  • the aldoxime represented by the general formula ( ⁇ ) is represented by the general formula (III) by halogenating with a halogenating agent in the presence or absence of an inert solvent and a base.
  • a halogenating agent in the presence or absence of an inert solvent and a base.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • water alcohols such as methanol and ethanol; aromatic hydrocarbons such as benzene, toluene and xylene; Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and dichloromethane; Esters such as ethyl acetate and methyl acetate; Tetrahydrofuran, Jetyl ether, Methyl t- Examples include linear or cyclic ethers such as butyl ether, 1,2 dimethoxyethane, 1,4 dioxane; -tolyls such as acetonitrile; polar solvents such as N, N dimethylformamide, N methylpyrrolidone, dimethyl sulfoxide, etc.
  • inert solvents can be used alone or in admixture of two or more. it can.
  • the base that can be used in this reaction include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkalis such as sodium carbonate and potassium carbonate Examples include metal carbonates; inorganic salts; pyridine, DBU (1, 8 diazabicyclone [5. 4. 0] undec 1-7), triethylamine, and other organic bases. If the reaction is carried out by appropriately selecting the molar excess of the aldoxime represented by (II) within the range of equimolar force.
  • halogenating agents examples include N-halosuccinimides such as N-chlorosuccinimide and N-bromosuccinimide; hypohalogen alkali metal salts such as sodium hypochlorite; hypochlorite Examples include hypohalous acid esters such as acid butyl ester; simple halogens such as chlorine gas; sulfuryl chloride and the like.
  • the amount used is generally equimolar to the aldoxime represented by the formula (II). If the reaction is to be selected appropriately within the range of molar excess.
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and is preferably room temperature to 80 ° C.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but is in the range of several minutes to 48 hours.
  • the hydroxamic acid halides represented by the general formula (III) are stable, they may be isolated from the reaction system containing the target product according to a conventional method, and if necessary, recrystallization, column chromatography, etc. By purifying, the target product can be produced from this material, but it can also be used in the next reaction without isolation. If the hydroxamic acid halides represented by the general formula (III) are unstable, the reaction solution can be used in the next reaction without purification.
  • This reaction can produce the desired product according to the method described in WO05Z085216 pamphlet.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform and dichloromethane; Esters such as methyl acetate, ethyl acetate, and butyl acetate; Linear or cyclic ethers such as lan, jetyl ether, methyl t-butyl ether, 1,2 dimethoxyethane, 1,4-dioxane; -tolyls such as acetonitrile; N, N-dimethylformamide, N-methylpyrrolidone, Examples thereof include polar solvents such as dimethyl sulfoxide, and these inert solvents can be used alone or in admixture of two or more.
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate and potassium hydrogen carbonate.
  • Alkali metal bicarbonates such as pyridine, N, N dimethylaminoline, 4- (dimethylamino) pyridine, DBU (1, 8 diazabicyclo [5.4.0] undec-7-ene), triethylamine
  • Organic bases such as tributylamine, etc., and the amount used can be appropriately selected within the range of an equimolar amount to the molar amount of hydroxamic acid represented by the general formula (III). And react.
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and is preferably room temperature to 80 ° C.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but is in the range of several minutes to 100 hours. Since this reaction is an equimolar reaction, equimolar amounts of hydroxamic acid halides represented by general formula (III) and olefins represented by general formula (IV) can be used. It is also possible to use an excessive amount of reactants!
  • the solvent is distilled off under reduced pressure, and water is added. And then extracted with an aromatic hydrocarbon solvent such as benzene, toluene or xylene insoluble in water; a halogenated hydrocarbon solvent such as chloroform or dichloromethane; an ester solvent such as ethyl acetate.
  • aromatic hydrocarbon solvent such as benzene, toluene or xylene insoluble in water
  • a halogenated hydrocarbon solvent such as chloroform or dichloromethane
  • an ester solvent such as ethyl acetate.
  • the solvent may be distilled off under reduced pressure.
  • a desiccant such as anhydrous sodium sulfate or anhydrous magnesium sulfate
  • water is added to the reaction mixture, and the mixture is separated.
  • the organic layer is washed with saturated brine, and then dried with a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate.
  • the solvent can be distilled off under reduced pressure.
  • the isoxazoline derivative represented by the general formula (I) of the present invention can be produced by purifying the residue obtained after distilling off the solvent by recrystallization, suspension washing, column chromatography or the like.
  • hydroxamic acid represented by the general formula (III) 1-2 equivalents of olefins represented by the general formula (IV) and 1 to 2 equivalents of sodium carbonate, hydrogen carbonate without isolation of the rides. It is preferable to add a base such as sodium or triethylamine and carry out the reaction for 10 minutes to 24 hours at a temperature ranging from 0 ° C to the boiling point of the solvent.
  • a base such as sodium or triethylamine
  • hydroxamic acid halides represented by the general formula (III) and the olephine derivatives represented by the general formula (IV), which are raw materials and compounds of the present invention, are prepared by the method described in WO05Z085216 pamphlet. Can be manufactured according to.
  • Q represents a carbo ol group or a sulpho group
  • R 6 represents (C to C) alkyl group, halo (C 1 -C 6) alkyl group,
  • the product can be reacted with a compound in the presence of a base in the presence or absence of an inert solvent to produce an amide derivative represented by the general formula (I 2).
  • the amide derivative and the halogenated compound represented by the general formula (VI) are reacted in the presence of a base in the presence or absence of an inert solvent to obtain an amide represented by the general formula (I3).
  • Derivatives can be produced.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; Halogenated hydrocarbons such as chloroform, dichloromethane, etc .; Esters such as methyl acetate, ethyl acetate, and butyl acetate; Tetrahydrofuran, Jet Chain or cyclic ethers such as tilether, methyl t-butyl ether, 1,2 dimethoxyethane, 1,4-dioxane; -tolyls such as acetonitrile; N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, etc. Polar solvents and the like, and these inert solvents can be used alone or Two or more types can be mixed and used.
  • Examples of the base that can be used in this reaction include metal hydrides such as lithium hydride, sodium hydride and potassium hydride; alkali metals such as sodium hydroxide and potassium hydroxide. ⁇ ; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; pyridine, N, N dimethylaline, 4 — (dimethylamino) pyridine, DBU (1, 8 diazabicyclo [5. 4. 0] undec 1-7), organic bases such as trytylamine, tryptylamine, etc., and the amount used is that of the amine derivative represented by the general formula (I 1). If you select the reaction in the range of equimolar to excess molar, you can react.
  • metal hydrides such as lithium hydride, sodium hydride and potassium hydride
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • alkali metal bicarbonates such as sodium bicarbonate and
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and is preferably room temperature to 80 ° C.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but is in the range of several minutes to 100 hours. Since this reaction is an equimolar reaction, the general formula (1-1) ) And the acid anhydride or acid halide or sulfonic acid anhydride or sulfonic acid halide represented by the general formula (V-1) or (V-2) Good, but V, you can use any of the reactants in excess!
  • the target compound can be isolated by carrying out the same isolation procedure as in [12].
  • This reaction may be carried out according to [2-1].
  • the isoxazoline derivative represented by the general formula (I1) which is the starting material compound of the present invention, can be produced according to the method described in International Publication No. 05Z085216.
  • the compound (I 5) in which W is represented by —SO 2 or —S 2 O— is produced, for example, by the production method illustrated below.
  • a sulfoxide derivative represented by the general formula (I 5) or a sulfoxide derivative represented by the general formula (I 4) is reacted with an oxidizing agent in the presence or absence of an inert solvent. Lufone derivatives can be produced.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • acetone, methyl ethyl ketone, methyl Ketones such as isobutyl ketone
  • halogenated hydrocarbons such as black mouth form and dichloromethane
  • water esters such as methyl acetate and ethyl acetate
  • Acids organic acids such as trifluoroacetic acid
  • polar solvents such as acetonitrile, N, N dimethylformamide, N-methylpyrrolidone, etc.
  • Examples of the oxidizing agent that can be used in this reaction include m-chlorobenzoic acid, hydrogen peroxide, and peracetic acid. Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of the sulfide derivative represented by the general formula (I 4) and the oxidizing agent, but it is also possible to use excessive amounts of any of the V reactants. Preferably, it is preferable to use an oxidizing agent in excess.
  • the reaction temperature is preferably in the range of ⁇ 50 ° C. to the boiling point of the inert solvent used, and is preferably in the range of 0 ° C. to 25 ° C.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but it is in the range of several minutes to 48 hours.
  • the target compound can be isolated by carrying out the same isolation procedure as in [12].
  • R 1 is a (C -C) alkyl group.
  • the amine compound represented by the general formula (I 1) and the ortho ester represented by the general formula (VII) are reacted in the presence or absence of an inert solvent to represent the general formula (IX).
  • an amine represented by the general formula (VIII) in an inert solvent By reacting with an amine represented by the general formula (VIII) in an inert solvent, the imidate derivative is isolated or not isolated, and represented by the general formula (I 6).
  • the compound of the present invention can be produced.
  • the amine derivative represented by the general formula (1-1) and the acid halide represented by the general formula (VII-1) are reacted in the presence of a base, in the presence or absence of an inert solvent.
  • an amide derivative represented by the general formula (I7) and the amide derivative is isolated or not isolated and reacted with a halogenating agent in the presence or absence of an inert solvent.
  • the imidoyl halide derivative represented by (IX-1) should be reacted with the amine represented by the general formula (VIII) in an inert solvent with or without isolating the imidoyl halide derivative.
  • the compound of the present invention represented by the general formula (I 6) can be produced.
  • orthoesters examples include, but are not limited to, lower alkyl orthoesters of lower fatty acids such as methyl orthoformate, ethyl orthoformate, methyl orthoacetate, and orthoethyl acetate.
  • an inert solvent can be used without inhibiting this reaction.
  • orthoesters it is preferable to use orthoesters as reactants as a solvent.
  • the reaction temperature is suitably in the range of the boiling point of the inert solvent or orthoester used, preferably 60 ° C to 120 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but it ranges from several minutes to 100 hours. Since this reaction is an equimolar reaction, if an equimolar amount of the amine derivative represented by the general formula (I 1) and the ortho ester represented by the general formula (VII) are used, it is good. It is preferable to use excessively.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons Aromatic hydrocarbons; Alcohols such as methanol, ethanol, isopropyl alcohol; Chain or cyclic ethers such as tetrahydrofuran, jetyl ether, methyl t-butyl ether, 1,2 dimethoxyethane, 1,4 dioxane; Acetonitrile -Tolyls such as: N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, water and other polar solvents, etc., and these inert solvents may be used alone or in combination of two or more. Can be used.
  • the reaction temperature is suitably in the range of 0 ° C. to the boiling point of the inert solvent used, preferably in the range of room temperature to 80 ° C.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but it is in the range of several minutes to 100 hours. Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of the imidate derivative represented by the general formula (IX) and the amines represented by the general formula (VIII). Preferably, an amine represented by the general formula (VIII) is preferably used in excess.
  • the inert solvent is distilled off, and the product can be purified by recrystallization, suspension washing, column chromatography or the like as necessary.
  • halogenating agents that can be used in this reaction, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus pentachloride, phosphorus tribromide, phosphorus pentabromide, salt thiol, thiobromide
  • the amount of the halogenating agent used may be appropriately selected and used within the range of equivalent to 5 equivalents relative to the amide derivative represented by the general formula (I7), but preferably 1.2 equivalents to 2 equivalents Range.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons such as benzene, toluene and xylene; halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons such as benzene, toluene and xylene
  • halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons such as benzene, toluene and xylene
  • halogenated compounds such as black benzene and dichlorobenzene.
  • Aromatic hydrocarbons such as benzene, toluene and xylene
  • halogenated compounds such as black benzene and dichlorobenzene.
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of 80 to 120 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but is in the range of several minutes to 100 hours.
  • the imidoyl halide derivative represented by the general formula (IX-1) can be isolated and purified by performing the same isolation procedure as [1-2], but without purification. It is preferable to use in the next reaction only by distilling off the inert solvent.
  • the compound to be produced can be produced, for example, by the production method illustrated below, but is not limited thereto.
  • the amine derivative represented by the general formula (I 1) is reacted with disulfuric acid carbon in the presence of a base, in the presence or absence of an inert solvent to form a dithiolate, and the dithiolate is generally isolated without isolation.
  • the compound of the present invention represented by the general formula (I 8) can be produced by reacting with a halide represented by the formula (VI-1).
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; Halogenated hydrocarbons such as form and dichloromethane; esters such as methyl acetate, ethyl acetate, and butyl acetate; tetrahydrofuran, jetyl ether, methyl t-butyl ether, 1,2 dimethoxyethane, 1,4-dioxane, etc.
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydrogen carbonate and potassium hydrogen carbonate Alkali metal bicarbonates such as pyridine, N, N dimethylaminoline, 4- (dimethylamino) pyridine, DBU (1, 8 diazabicyclo [5.4.0] undec-7-ene), triethylamine Organic bases such as tributylamine and the like, and the amount used thereof is appropriately selected within the range of excess moles with respect to the amine derivative represented by the general formula (1-1). Just do it.
  • alkali metal hydroxides such as sodium hydroxide and potassium hydroxide
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • Alkali metal bicarbonates such as pyridine, N, N dimethylaminoline, 4- (dimethylamino) pyridine, DBU
  • the reaction temperature is suitably in the range of 0 ° C to the boiling point of the inert solvent used, and is preferably in the range of room temperature to 80 ° C.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but it is in the range of several minutes to 100 hours. Since this reaction is an equimolar reaction, equimolar amounts of the amine derivative represented by the general formula (I-1), carbon disulfide, and the halogenated compound represented by (VI-1) may be used. You can use any of the reactants in excess!
  • the target compound can be isolated by the same isolation procedure as [12].
  • a compound in which W is a sulfur atom or W—R 1 is SO NR 12 R 1C> is produced by, for example, the production method illustrated below.
  • R 12 and R 12 may be the same or different, a hydrogen atom, a (C to C) alkyl group or Z (Z is Same as
  • a fluorine compound represented by the general formula (I 9) and sodium thiomethoxide are reacted in the presence of an inert solvent to obtain a sulfide derivative represented by the general formula (I-4a).
  • the sulfoxide derivative represented by the general formula (I-5a) is reacted with an oxidizing agent in the presence of an inert solvent without separation or isolation, and the sulfide derivative is isolated or separated by Pummerer reaction without isolation.
  • the thiol derivative represented by the general formula (I 10) is reacted with the halide represented by the general formula (VI) in the presence of a base and an inert solvent without or isolating the thiol derivative.
  • the compound of the present invention represented by the general formula (I 4) can be produced.
  • the thiol derivative represented by the general formula (1-10) is reacted with a halogenating agent to form a sulfonyluride derivative represented by the general formula (X), and the sulfornolide derivative is isolated or
  • the compound of the present invention represented by the general formula (I11) can be produced by reacting the amine represented by the general formula (VIII-1) in the presence of a base and an inert solvent without isolation. It can be done.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • it is an aromatic hydrocarbon such as benzene, toluene, xylene, or the like; Aromatic hydrocarbons; linear or cyclic ethers such as tetrahydrofuran, diethyl ether, methyl t-butyl ether, 1,2 dimethoxyethane, 1,4 dioxane; -tolyls such as acetonitrile; N, N-dimethylformamide, Examples thereof include polar solvents such as N-methylpyrrolidone, dimethyl sulfoxide, and water. These inert solvents can be used alone or in combination of two or more.
  • Reaction temperature is 0 ° C to use.
  • the temperature is preferably in the range of room temperature to 80 ° C., preferably in the range of the boiling point of the inert solvent.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but it is in the range of several minutes to 100 hours. Since this reaction is an equimolar reaction, an equimolar amount of the fluorine compound represented by the general formula (I 9) and sodium thiomethoxide may be used. Either of these reagents may be used in excess.
  • This reaction may be carried out in the same manner as in production method 3.
  • This reaction is a production method known as Pummerer reaction or Pummerer rearrangement, and is known in the literature (for example, Chem. Ber., 43, p. 1401 (1910), Org. React., 40, p. 157 (1991) or ⁇ . Am. chem. Soc., 106, p. 4186 (1984) etc.).
  • (X) m represents a 3,5-bis (trifluoromethyl) group
  • R 2 represents trifluoromethyl.
  • the compound (IV-1) showing a group can be produced by the production method shown below.
  • Si (OEt) group —ZnCl group, ZnBr group, —Znl group, —MgCl group, —MgBr group, or Mgl
  • J 2 is chlorine atom, bromine atom, iodine atom, -B (OH)
  • a leaving group such as an OMe) group or a -B (OEt) group.
  • catalysts that can be used in this reaction include various paraffinic compounds having a zero-valent or divalent coordination state. Mention may be made of dimethyl or nickel complexes.
  • the ligands that can be used in this reaction are tri-t-butylphosphine, tricyclohexylphosphine, triphenylphosphine, tri 0-trinolephosphine, 1,2 bisdiphenylphosphinoethane, 1,3 bisdiphenylphosphinopropane. 1, 4 bisdiphenylphosphinobutane and other phosphorus ligands, naphthyridine, tetramethylethylenediamine, 8-oxoquinoline and other nitrogen-containing ligands. Absent.
  • the amount of the ligand used may be appropriately selected within a range of 0.1 to L00 times mol with respect to 1 mol of the palladium or nickel catalyst, but preferably 2 to L
  • the reaction can also be carried out without using a
  • Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate.
  • Metal bicarbonates pyridine, N, N-dimethylaline, 4- (dimethylamino) pyridine, DBU (1,8 diazabicyclo [5.4.0] undec-7-en), triethylamine, tributyl Organic bases such as amines can be mentioned, and the amount used is equimolar force with respect to the 3,5-bis (trifluoromethyl) benzen derivative represented by the general formula (XI).
  • the reaction may be performed by selecting as appropriate.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the reaction.
  • aromatic hydrocarbons such as benzene, toluene, and xylene; acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.
  • Ketones halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; organic acids such as formic acid, acetic acid and trifluoroacetic acid; acetonitrile, N, N dimethylformamide, N -Polar solvents such as methylpyrrolidone can be mentioned, and these inert solvents can be used alone or in admixture of two or more.
  • the reaction temperature is suitably in the range of 50 ° C. to the boiling point of the inert solvent used, and preferably in the range of room temperature to 80 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but is in the range of several minutes to 100 hours.
  • Pesticides containing the isoxazoline derivative represented by the general formula (I) of the present invention as an active ingredient particularly agricultural and horticultural insecticides include paddy rice, fruit buds, vegetables, other crops and flowers. It is suitable for various harmful forests, horticulture, stored grain pests, sanitary pests, nematodes, and other pests.
  • Adoxophyes orana fasciata For example, Adoxophyes orana fasciata, Adoxophyes sp., Apple cinchoy (Grapholita) inopinata, Grapholita molesta, Leguminivora glycinivorella, lettuce mori, Caloptilia thevivora, Caloptilia zacnrysa, pulmona, 7 White butterfly (Piers rapae crucivora), white tobacco (Heliothis sp.), Codling moth (Lasp ey resia pomonella, Plutella xylostella), Argyresthia conj ugella, Peach squid (Carposina niponensis), -Kameika Chilo suppressalis), Cnaphalocrocis medinalis, Ephestia elutelia, cily saga Parnara guttata, Pseudaletia separata,
  • Lepidopterous insects such as Sesamla inferens, Spodoptera litura, Spodoptera egigua, Macrosteles fascifrons, Nephotettix cincticeps, lu Ns Power (Sogatella forcifera), citrus white lice (Diaphorina citri), grape whitefly (Aleurolob us taonabae), white lice whitefly (Bemisia tabaci), white horned lice (Trialeurodes va porariorum), black pea aphid (Myzus persicae), Nororumun (Ceroplastes cenferus), Citrus serrata 7 (Pulvinana a urantii), Citrus reindeer (Pseudaonidia duplex), Nasimana scales (Corns tockaspis perniciosa), Yanounkai!
  • Hemiptera Unaspis yanonensis
  • Pratylenchus sp. Anomala rufocuprea
  • Japanese beetle P opilla japonicano, Tano, Lasnoderma serricorne
  • Pesticides such as Meloidogyne sp., Tylenchulus semipenetrans, Aphelenchus avenae, and Aphelenchoide s ritzemabosi ), Ringochu Gumi (Panonychus uimi, -Tetranychus cinnabarinus), Leztranychus anzawal Kishiaa), Tetanoychus urticae Koch, Aephylla - against mite-like pests such as (Aculops pelekassi), Cyanosavidi (Calacarus carinatus), Nasisida-(Epitrimerus pyri) It has a strong insecticidal effect.
  • Rhinotermitidae Coptotermes formosan us Shiraki
  • white-tailed termites Reticulitermessperatus (Kolbe)
  • North American Reticulitermes hesperus Reticulitermes tibialis ⁇ Reticulitermes flavipe Reticulitermes lucifugus, Reticulitermes santonensis, etc.
  • American licorice termites Incisitermes minor (Hagen)
  • Ho dotermopsis jzponica Holmgren of Termopsidae It has a remarkable anticide effect at a low dose.
  • formicidae (Monomorium ph araoni Linnes), ⁇ / 'li (Monomorium nipponense Wheeler), 7J roffori (Campon otus kiusiuensis bantschi), Kuroama, Ri (Formica japonica Motschulsky), Kurosari (Lasius luliginosus (Latreille)) and fire ant inhabiting North America (Solenops is richteri, Solenopsis invicta, Solenopsis geminata (F)), etc. It has a significant ant killing effect even at low doses.
  • the isoxazoline derivative represented by the general formula (I) of the present invention includes domestic animals such as cattle, horses and sheep, pets such as dogs and cats, mice, rats, rats, musters, squirrels and the like. It can also be used against rodents, maggots, carnivorous animals such as frets, and ectoparasites of birds such as ducks, -birds, and pigeons.
  • cat fleas (Ctenocephalides felis) nis)
  • flea eye pests such as Xenopsylla cheopis, Taetoid tick (Hae maphyxalis longicornis), double eye pests such as Boophilus microplus, Haematopinus eurysternus, Hidagi vis, etc. It has a strong insecticidal effect against ectoparasites such as lice pests.
  • Pesticides containing the isoxazoline derivative represented by the general formula (I) of the present invention as an active ingredient are paddy field crops, field crops, fruit crops, vegetables, and other crops. And has a remarkable control effect against the above-mentioned pests that cause damage to the flower buds, etc. Seedling facilities, paddy fields, fields, fruit pods, vegetables, other crops, flower seeds, paddy water, foliage, or soil before the occurrence of pests or when the occurrence is confirmed, in accordance with the expected life
  • the desired effect of the agricultural and horticultural insecticide of the present invention can be exhibited by treating it with a cultivation carrier such as the above.
  • Plants to which the pest control agent of the present invention, in particular, agricultural and horticultural insecticides can be used are not particularly limited, and examples thereof include the following plants.
  • Cereals eg, rice, barley, wheat, rye, oats, corn, etc.
  • beans soybeans, red beans, broad beans, peas, kidney beans, peanuts, etc.
  • fruit berries apples, citrus fruits, pears
  • Persimmon peach, plum, yellow peach, walnut, chestnut, almond, banana, strawberry, etc.
  • leaf 'fruit and vegetables cabbage, tomato, spinach, broccoli, lettuce, onion, leek, pepper, eggplant, pepper, etc.
  • Root vegetables carbrots, potatoes, sweet potatoes, taros, radishes, lotus roots, turnips, burdock, garlic, etc.
  • processing crops salmon, hemp, beet, hops, sugar cane, sugar beet, olives, gum
  • Coffee, tobacco, tea, etc. cucumbers (cabochia, cucumber, matawauri, watermelon, melon, etc.), pastures (orchard grass, sorghum, timosi, clover, alfa alpha, etc.), turf (Korai turf, bentgrass) Etc.), crops for appreciation such as fragrances (lavender, rosemary, time, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, etc.), garden trees (such as ichiyo, cherry, aoki) It can be used for plants such as forest trees (Todomatsu, Ezomatsu, pine, hiba, cedar, firewood, etc.).
  • the pest control agent of the present invention is used to control various pests. It is sufficient to use an effective amount for controlling pests or nematodes in the form of nematodes or nematodes in a form diluted or suspended appropriately with water or the like.
  • seed treatment such as soaking in seeds, seed dressing, calper treatment, etc.
  • soil such as floor soil admixture, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface treatment, etc. It can be used by application to nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
  • the pest control agent of the present invention is expected to be generated in an amount effective for pest control as it is, or appropriately diluted or suspended in water or the like.
  • the pest control agent of the present invention in addition to spraying on stored grain pests, house pests, sanitary pests, forest pests, etc., it can also be used for application to house building materials, smoke, bait, etc.
  • the seed treatment method includes, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to penetrate the drug, and the solid preparation or liquid preparation is mixed with the seed.
  • a method of dressing and adhering to the surface of the seed examples thereof include a method of dressing and adhering to the surface of the seed, a method of coating the seed by admixing with an adhesive carrier such as rosin and polymer, and a method of dispersing near the seed at the time of planting.
  • the “seed” for the seed treatment means an initial plant body used for plant propagation.For example, in addition to seeds, bulbs, tubers, seed buds, buds, baskets, bulbs, or cuttings The plant for vegetative propagation can be mentioned.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention indicates a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, as long as it is a material that plants can grow on, so-called soil, seedling mats, water, etc., specific materials such as sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances It may be a polymer substance, rock wool, glass wool, wood chip, bark or the like.
  • the method include a method of appropriately diluting a liquid preparation such as an emulsion and a flowable preparation or a solid preparation such as a wettable powder or a granular wettable powder with water, a method of spraying a powder, a smoke or the like.
  • Application methods to soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or seedling nursery, etc., and a granule is used for plant stock or seedling raising.
  • Spraying seedling beds, etc. spraying powder, wettable powder, granulated wettable powder, granules before sowing or transplanting and mixing with the whole soil, planting holes before sowing or planting, Examples include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the application time, for example, application during sowing, greening period, application during transplantation, etc., but powder, granule wettable powder, granule It may be applied in the dosage form. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with floor soil, mixed with cover soil, or mixed with the entire soil. Simply, the soil and the various preparations may be applied alternately in layers.
  • liquid preparations such as solid preparations such as jumbo agents, knocking agents, granules, granule wettable powders, flowables, and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • chemicals such as emulsion and flowable as the source of water flow into the paddy field such as water mouths and irrigation devices, it can be applied in a labor-saving manner with the supply of water.
  • the seeding power can be treated to the cultivation carrier or the like close to the seed or the plant body in the seedling raising stage.
  • treatment on the plant source of the plant being cultivated is suitable. It is possible to irrigate the drug in a liquid state without using a granule to spray or dilute or dilute in water. It is also preferable to mix the granule with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the spraying treatment of the granule on the seedling nursery is preferable.
  • the agricultural and horticultural insecticide of the present invention is generally used after being formulated into a convenient shape in accordance with conventional methods for agricultural chemical formulations.
  • optically active phthalamide derivative represented by the general formula (I) is dissolved, separated, suspended, mixed by mixing these in an appropriate inert carrier, or if necessary, together with an auxiliary agent. It may be used after being impregnated, adsorbed or adhered and formulated into an appropriate dosage form such as a suspension, emulsion, liquid, hydrating agent, granule wettable powder, granule, powder, tablet, pack.
  • the inert carrier that can be used in the present invention may be either solid or liquid.
  • the material that can be a solid carrier include soybean flour, cereal flour, wood flour, husk flour, and saw. Powder, Tabacco stem powder, Tarmi shell powder, bran, fiber powder, residues after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talc ( For example, talc, pyrophyllite, etc.), silicas (for example, diatomaceous earth, quartz sand, mica, white carbon (some synthetic high-dispersion silicic acid, also called hydrous finely divided silicon, hydrous silicic acid, and some products contain calcium silicate as the main component).
  • Activated carbon iow powder, pumice, calcined diatomaceous earth, longa pulverized product, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, polyethylene, polypropylene, polysalt Plastic carriers such as spoon Biyuriden, ammonium sulfate, ammonium phosphate, ammonium nitrate, can be mentioned urea, fertilizer salts depreciation etc., compost and the like, they alone young properly used in the form of a mixture of two or more.
  • liquid carrier in addition to those that have solvent ability per se, the ability to disperse the active ingredient compound with the aid of an auxiliary agent without having solvent ability is selected.
  • the following carriers can be exemplified as typical examples.
  • ком ⁇ онентs eg, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.
  • ketones eg, acetone, methyl ethyl ketone, Methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.
  • ethers eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.
  • aliphatic hydrocarbons eg, kerosene, mineral oil, etc.
  • aromatic carbonization Hydrogen for example, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, etc.
  • halogenated hydrocarbons for example, dichloroethane, chloroform, carbon tetrachloride, chlorinated
  • adjuvants are shown below, but these adjuvants are used depending on the purpose, and used alone, in some cases, in combination with two or more kinds of adjuvants, and in other cases, It is also possible to use no adjuvants at all.
  • polyoxyethylene alkyl ether polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene succinate, polyoxyethylene sorbitan Surfactants such as monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate, lignosulfonate, and higher alcohol sulfate can be used.
  • adhesion and Z or bonding for example, casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polybutyl alcohol, pine root oil, coconut oil, bentonite, capita sulfonate, etc. Can be used.
  • casein gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, polybutyl alcohol, pine root oil, coconut oil, bentonite, capita sulfonate, etc.
  • waxes, stearates, alkyl phosphates, etc. can be used.
  • naphthalenesulfonic acid condensate for example, condensed phosphate, etc.
  • an antifoaming agent for example, silicone oil or the like
  • 1,2-benzisothazoline 3 On, parachlorometaxylenol, butyl paraoxybenzoate, and the like can be used.
  • activity enhancers such as metabolic degradation inhibitors such as pipette-rubutoxide, antifreezing agents such as propylene glycol, anti-oxidation agents such as BHT, UV absorbers, etc.
  • antifreezing agents such as propylene glycol
  • anti-oxidation agents such as BHT, UV absorbers, etc.
  • Other adjuvants can also be used.
  • the compounding ratio of the active ingredient compound can be adjusted as necessary, and it can be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of pest control agents, especially agricultural and horticultural insecticides.
  • pest control agents especially agricultural and horticultural insecticides.
  • 0.01 to 50% by weight is appropriate.
  • the amount of the pest control agent of the present invention, particularly the agricultural and horticultural insecticide is used for various factors, for example, purpose, target pest, crop growth status, occurrence tendency of pest, weather, environmental conditions, dosage form, application Depending on the method, place of application, time of application, etc., the active ingredient compound per 10 ares is 0.001 to 10 kg, preferably ⁇ or more. Olg to: Lkg range force can be selected according to the purpose. .
  • the pesticides of the present invention are other pesticides to be controlled, other agricultural and horticultural insecticides, pesticides, for the purpose of expanding the appropriate period of control or for reducing the dose.
  • Other agricultural and horticultural insecticides, acaricides and nematicides used for this purpose include, for example, ethion, trichlorfone, methamidophos, acephete, dichlorvos, mevinphos, monocrotophos, malathion, dimethoate, formotethione, mecarbam, bamidthione, thiomethoate. , Disulfotone, oxydeprophos, nared, methyl parathion, fe-trothion, cyanofos, propofos,
  • Agricultural and horticultural fungicides used for the same purpose include, for example, sulfur, lime-sulfur mixture, basic copper sulfate, iprobenfos, edifenphos, torque port phos'methyl, tyram, polycarbonate, dineb, manzeb , Mancozeb, propineb, thiophanate, thiophanate methyl, benomyl, iminotadine acetate, iminotazine arbesylate, meprol, furtranyl, pencyclon, furamethopyl, tifluzamide, metalaxyl, oxadixil, carpropamide, diclofluanide, Fluorsulfamide, chlorotamol, taresoxime methyl, phenoxanyl, himexazole, etalomezol, fluorimido, procymidone, bisulfide Ncrozolin, iprodione, triazime
  • herbicides include, for example, darifosate, sulfosate, dalfosinate, bialaphos, butamifos, esprocarb, prosulfocarb, beven curve, pyribticanolev, ashram, linuron, diimron, isouron, bensulfuron methyl, cyclosulfamuron, sinosulfuron, pyra Zosulfuronethyl, azimus noreflon, imazos noreflon, tenino le clonore, araclono nore, pretila clonore, clomeprop, etobenzanide, meenaset, flufenaset, phentolazamide, pendimethalin, bifenox, assiflufen , Lactofen, cyhalohop butyl, ioxinyl, bromobutide, ar
  • biological pesticides for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect box virus ( Entomopox virus (EPV) and other virus preparations, Monocrosporium phymatophagum, Steiner Microneochemicals used as insecticides or nematicides such as Steinernema carpocapsae, Steinernema 'Stein ernema kushidai, Pasteuria penetrans, Trichoderma lignorum, Trichoderma lignorum, Bacterium 'Agrobacterium radiobactor', microbial pesticides used as fungicides such as non-pathogenic erbium, Erwinia carotovora, Bacillus subtilis, Zantomonas' campest
  • microbial pesticides used as fungicides such as non-pathogenic erbium, Erwinia carotovora, Bacillus
  • reaction solution was poured into ice water and extracted with ethyl acetate.
  • organic layer is made of anhydrous magnesium sulfate.
  • residue was purified by silica gel column chromatography to obtain 0.32 g of the desired product.
  • reaction mixture was poured into water (20 ml), extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 0.46 g of the desired product.
  • Refractive index n 1.5474 (20. 3 ° C)
  • the solvent was distilled off under reduced pressure, and this was added to a solution of 0.5 g (4.6 mmol) of 2-pyridylmethylamine and 1.0 ml of chloroform (30 ml) under ice-cooling and stirred for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100 ml), washed with water, saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.07 g of the desired product.
  • the above is uniformly mixed and pulverized to obtain a powder.
  • the above is uniformly mixed and ground to obtain a wettable powder.
  • Test Example 1 Insecticidal test against Plutella xylostella
  • Mortality rate (%) X 100 Number of hatching insects in the untreated section Judgment criteria.
  • Cabbage leaf pieces (variety: four seasons) are immersed for about 30 seconds in a chemical solution containing the compound of the present invention as an active ingredient diluted to 500 ppm. After that, it was covered and placed in a constant temperature room at 25 ° C. Eight days after the inoculation, the number of live and dead insects was investigated, and the death rate was calculated according to the following formula. 1 ward, 10 heads, 2 trains. The results are shown in Table 10.
  • Test Example 3 Insecticidal test against Adoxophyes sp.
  • the compounds of the present invention are effective against harmful pests, particularly agricultural and horticultural pests, which have a low impact on the global environment. Therefore, it is useful as a pest control agent having a low dose and a broad control spectrum and exhibiting an excellent control effect, particularly an agricultural and horticultural insecticide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Le problème à résoudre dans le cadre de la présente invention consiste à proposer un nouvel agent insecticide, en particulier un insecticide agricole et horticole, qui est efficace contre les parasites présentant une résistance aux pesticides déjà existants et qui convient à une application allégeant la masse de travail pour des ouvriers agricoles âgés. La solution proposée est un agent insecticide comprenant un dérivé isoxazoline représenté par la formule (I) ou un sel de celui-ci en tant que substance active. (I) où R1 représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1 à C6 ou analogues ; R2 représente un groupe halogénoalkyle en C1 à C6 ; W représente un atome d'oxygène, un atome de soufre ou analogues ; A1, A2 et A3 représentent indépendamment un atome d'azote, C-H ou C-Y ; X représente un atome d'halogène, un groupe cyano, un groupe nitro ou analogues ; m représente un nombre entier dans la gamme de 1 à 5 ; Y représente un atome d'halogène, un groupe cyano, un groupe nitro ou analogues ; n représente un nombre entier dans la gamme de 0 à 4 ; et Z représente un atome d'halogène, un groupe cyano, un groupe nitro ou analogues.
PCT/JP2007/059040 2006-04-28 2007-04-26 Derive isoxazoline, agent insecticide et utilisation de l'agent insecticide WO2007125984A1 (fr)

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