WO1999002507A1 - Composes d'isoxazole, procede de preparation desdits composes, ainsi qu'insecticides et acaricides - Google Patents

Composes d'isoxazole, procede de preparation desdits composes, ainsi qu'insecticides et acaricides Download PDF

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Publication number
WO1999002507A1
WO1999002507A1 PCT/JP1998/003065 JP9803065W WO9902507A1 WO 1999002507 A1 WO1999002507 A1 WO 1999002507A1 JP 9803065 W JP9803065 W JP 9803065W WO 9902507 A1 WO9902507 A1 WO 9902507A1
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Prior art keywords
group
alkyl
substituted
compound
halogen atom
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PCT/JP1998/003065
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English (en)
Japanese (ja)
Inventor
Yasushi Shibata
Koichiro Aoyagi
Naomi Ichikawa
Hidemitsu Takahashi
Takao Iwasa
Masahiro Kawaguchi
Takehiko Nakamura
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Nippon Soda Co., Ltd.
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Priority to AU81272/98A priority Critical patent/AU8127298A/en
Publication of WO1999002507A1 publication Critical patent/WO1999002507A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—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
    • 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
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • Isoxazole compounds their preparation and insecticides and acaricides
  • the present invention relates to a novel isoxazole compound, a method for producing the same, and an insecticide / miticidal agent.
  • An object of the present invention is to provide a pesticidal agent which has a certain effect and can be used safely.
  • the present invention provides a compound represented by the general formula (1):
  • ⁇ represents a heterocyclic group which may be substituted with G or a phenyl group which may be substituted with G
  • G represents a nitro group, a cyano group, a halogen atom, a 6- alkyl group.
  • alkylsulfonyl 6 alkyl group Application Benefits ⁇ alkylsilyl C i-6 alkyl group, an alkoxycarbonyl group, d-6 Al kills good Fuweniru CH alkyl optionally substituted with a group group, optionally substituted downy Njiruokishi group with a halogen atom, a naphthyl group, a thienyl group, (halogen atom, C -6 alkyl group or a C, -!
  • haloalkyl group may be substituted with 6 haloalkyl group) pyridyl group, (nitro group, Shiano group, a halogen atom, (6 alkyl group, C, - S haloalkyl group, C iB alkoxy group, Mechirenjiokishi group, C -! 6 haloalkoxy group, C l-6 alkylthio group, alkylsulfinyl group , C -!.
  • 6 Arukirusu Ruhoniru group, alkyl group, alkylamino amino group, di ⁇ alkylamino Bruno may be substituted with a group) Hue sulfonyl The expressed.
  • G may form form a 5- or 6-membered ring by a C 3 4 alkylene group bonded with a substituent positions adjacent.
  • the heterocyclic group which may be substituted with W is triazolyl, thiazolyl, oxosazolyl, isoxazolyl, isothiazolyl, virazolyl, imidazolyl, tetrazolyl, oxadiazolinolone, thiaziazolyl, chenyl, furyl, It is a group selected from the group consisting of pyrrolyl, pyridyl and pyrimidinyl.
  • B is a phenyl group or a naphthyl group represented by the following formula:
  • 6 represents an alkoxy group, a 6 haloalkyl group or a C-nitroalkoxy group
  • R 2 is a hydrogen atom, a nitro group, Shiano group, a halogen atom, C, - 6 alkyl group,
  • R 3 represents a nitro group, a cyano group, a halogen atom, a dealkyl group, a 6- alkyl group, a 6- alkoxy group or a Cn-haloalkoxy group, m represents 0, 1, 2 or 3. When m is 2 or more, R 3 may be the same or different. )
  • Hajime Tamaki (W substituted in W, a nitro group, Shiano group, Ha androgenic atom, ⁇ , - 6 alkyl group, a haloalkyl group, an alkoxy group,
  • R is a hydrogen atom, C, - 6 alkyl or C -! To Table 6 alkoxycarbonyl two Le group.
  • the substituents G and W may be the same or different.
  • R 4 represents a hydrogen atom or a dealkyl group
  • R 5 represents a d- 6 alkyl group
  • R 4 and R 5 And may together form a ring.
  • the present invention is a pesticidal composition
  • a pesticidal composition comprising one or more of the compounds represented by the general formula (1) as an active ingredient.
  • the present invention provides, as an active ingredient, a compound represented by the general formula (1), a method for producing the compound, and one or more compounds represented by the general formula (1) as described above. It is a pest control agent characterized by the following.
  • A represents a heterocyclic group optionally substituted with G or a phenyl group optionally substituted with G;
  • G is a halogen atom such as a nitrogen atom, a cyano group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl atom, a propyl atom, an isopropyl atom, a butyl atom, an isobutyl atom, a sec-butyl, a t-butyl atom, a pentyl atom, C! -E alkyl groups such as xyl,
  • C such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 1-methyl-1-2-propenyl, 1-methyl-2-butenyl 2 - 6 alkenyl group,
  • C alkynyl groups such as ethynyl, 1_propynyl, 1-butynyl, 2-propynyl, 2_pentynyl,
  • Fluorometyl 1 1 Fluoroethyl, 2 — Fluoroethyl, Difluorometyl, Trifluoromethyl, Chlorometyl with phenolic, Difluorochloromethyl, Trik rometyl, Promomethyl, 2, 2, 2 — Trifluoroethyl (hereinafter, simply referred to as "Application Benefits Furuoroechiru”.), C 6 C, such as penta full O Roe chill Mouth alkyl group,
  • Alkylsulfonyl Ci alkyl groups such as propylsulfonylmethyl, isopropylsulfonylmethyl, and butylsulfonylmethyl;
  • Trialkylsilylalkyl groups such as trimethylsilylmethyl, trimethylsilylethyl, and triethylsilylmethyl;
  • C alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, and t-butoxycarbonyl;
  • a phenyl C alkyl group which may be substituted with a d alkyl group such as benzyl, phenethyl, ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl, A benzyloxy group which may be substituted at any position of the benzene ring with a halogen atom such as fluorine, chlorine, bromine or iodine;
  • Naphthyl group such as 1-naphthyl, 2-naphthyl, phenyl group such as 2-phenyl, 3-phenyl,
  • a pyridyl group such as 2-pyridyl, 3-pyridyl, 4-pyridyl, etc., which may be substituted at any position of the pyridin ring with a halogen atom, an alkyl group or a 6-haloalkyl group;
  • C is set to -6 alkylamino amino group, Mechirua Mi Bruno, Echiruami Bruno, flop port Piruami Bruno, isopropyl ⁇ Mi Roh, etc.
  • Puchirua Mi Bruno is as a di-C i -6 Arukirua Mi amino group Examples include dimethylamino, getylamino, ethylisopropylamino, dipropylamino and the like.
  • G propylene bound substituted position Adjacent, C 3 of butylene - may form a 5- or 6-membered ring by 4 Ryo alkylene group.
  • G is, C t-6 alkyl group, C 3 - 8 cycloalkyl group, a halogen atom, alkyl group, or a C -! 6 haloalkyl optionally pyridyl group optionally substituted with a group, nitro group , Cyano group, halogen atom, 6 alkyl group, Ci-6 haloalkyl group, alkoxy group, methylenedioxy group, peroxyalkoxy group, C1-6 alkylthio group, Ci- 6 alkylsulfinyl group, 6 alkylsulfonyl group , d -e alkyl group, alkylamine Mi amino group, di ⁇ I s ⁇ Rukirua Mi Roh more preferred arbitrarily good Fuweniru group optionally substituted with a group.
  • the heterocyclic group which may be substituted with G includes triazolyl, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, vilazolyl, imidazolyl, tetrazolyl, oxaziazolyl, thiadiazolyl, chenyl, furyl, pyrrolyl, A group selected from the group consisting of pyridyl, pyrimidinyl and birazinyl.
  • Preferred heterocyclic groups include 1,2,4—triazole 1-yl, 1,2,4—triazole-3_yl, and 2,4_triazole-5-yl , 1, 3, 4-triazole _ 2-yl, 1, 2, 3-triazole-4-yl, 1, 2, 3-triazole-5-yl, thiazo Lou 2 — yl, thiazol _ 4 _ yl, thiazolul 5 — yl, oxazol 2 — yl, oxazol 4 -1 yl, oxoxazolu 5 — yl, isoxoxol 3 — 3 L-isoxazole-4_yl, isoxoxazol-5_yl, isothiazolu-3_yl, isothiazolu-4_yl, isothiazol-5-yl, pyrazole-1-yl, Virazol 1 3-yl, pyrazole-4 yl, pyrazol-5 _
  • B is a phenyl group, a naphthyl group represented by the following formula,) m Or a heterocyclic group which may be substituted with W,
  • R 1 is a nitro group, a cyano group
  • Halogen atoms such as fluorine, chlorine, bromine, and iodine
  • Alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec—butyl, t_butyl, pentyl and hexyl;
  • Trifluoromethoxy, 1,1,2,2—Ci-haloalkoxy groups such as tetrafluoroethoxy, trichloromethoxy and difluoromethoxy.
  • R 2 represents a hydrogen atom, a nitrogen atom, a cyano group
  • Halogen atoms such as fluorine, chlorine, bromine, and iodine
  • Alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec—butyl, t—butyl, pentyl, hexyl,
  • Fluoromethyl 1 Fluoroethyl, 2 — Fluoroethyl, Difluoromethyl, Trifluoromethyl, Fluorochloromethyl, Difluorochloromethyl, Triclomethyl, Bromomethyl, Trifluoroethyl, Pentafluoroethyl Which 6 haloalkyl groups,
  • C, -6 alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy,
  • haloalkoxy group such as trifonolomethoxy, 1,1,2,2-tetrafluoroethoxy, trichloromethoxy, difluoromethoxy, etc.
  • R 3 is a halogen atom such as a nitro group, a cyano group, fluorine, chlorine, bromine, and iodine;
  • C ⁇ 6 alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, t-butoxy,
  • Fluorometil 1 — Fluoroethyl
  • 2 Fluoroethyl, diphnoleolomethyl, trifluorometyl, fluorochrome, methyl, trifluoromethyl, trimethylol, methyl, promotyl, trifluorethyl, penfluolochol, etc. 6 haloalkyl group,
  • Trifluoromethoxy 1,1,2,2- Represents a haloalkoxy group such as tetrafluoroethoxy, trichloromethoxy, difluoromethoxy.
  • n 0, 1, 2 or 3
  • R 3 may be the same or different.
  • W is a nitro group, a cyano group
  • Halogen atoms such as fluorine, chlorine, bromine, and iodine
  • Alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isoptyl, sec—butyl, t-butyl, pentyl and hexyl;
  • Furuoromechiru 1 one Furuoroechiru, 2 - Furuoroechiru, Jifuruorome Chi le, Application Benefits Furuoromechiru, Furuorokurorome chill, Jifuruoroku Roromechiru, Application Benefits click port Romechiru, bromomethyl, Application Benefits Furuoroechiru, pentaerythritol full O Roe chill of which C, - 8 haloalkyl group, Trifluoromethoxy, 1,1,2,2—Represents haloalkoxy groups such as tetrafluoroethoxy, trichloromethoxy, difluoromethoxy and the like.
  • heterocyclic group which may be substituted by W examples include triazole, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, virazolyl, imidazolyl, tetrazolyl, oxaziazolyl, It is a group selected from the group consisting of thiadiazolyl, chenyl, furyl, pyridine, pyridyl, pyrimidinyl, and virazinyl. ).
  • Preferred heterocyclic groups include 1,2,4—triazole—3—yl, 1,2,4,1 triazole_5—yl, 1,3, 4 — Triazole 2 — yl, 1, 2, 3 — Triazole — 4 _yl, 1, 2, 3 — Triazole — 5 — yl, Thiazolu 2 — yl, Thiazole _ 4 yl, thiazole 5-yl, oxazo 1-2 yl, oxazo 1-4, yl, oxazo 1-5, yl, isoxoxazole _ 3 _, isoxox 4 Ill, Isoxazolu 5 — Ill, IsothiazoI — 3 — Ill, Isothiazole 4 Ill, Isothiazo Iru 5 — Ill, Virazo Iru 3 Ill, Pyrazole 4-yl, pyrazole-5-yl, imidazole-2-yl, imidazo
  • pyrazolyl groups such as pyrazole-3-yl, pyrazolyl-4-yl and pyrazolyl-5-yl are more preferred.
  • the substituents G and W may be the same or different.
  • the compound of the present invention can be produced by the following method.
  • R 4 and R 5 represent the same meaning as described above.
  • R 4 and R 5 may be taken together to form a 3- to 8-membered ring.
  • the compound represented by the formula (1) can be obtained by reacting the compound represented by the formula (2) with hydroxylamine or a salt thereof.
  • the reaction involves alcohols such as methanol, ethanol, and 2-methoxyethanol; hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform and dichloromethane; and N, N-dimethyl.
  • solvents such as formamide (DMF), dimethylsulfoxide (DMS0) and hexamethylphosphoramide (HMPA), the temperature ranges from 0 ° C to the boiling point of the solvent used.
  • salts of hydroxyamine used in the reaction examples include hydrochloride, sulfate, oxalate and the like. If desired, a catalyst such as p-toluenesulfonic acid, sulfuric acid or Lewis acid may be added.
  • the compound represented by the general formula (2) can be produced by the method shown in the following (a) or (b). 99
  • R 6 represents an alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy group, dimethylamino, getylamino
  • R 6 represents an alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy group, dimethylamino
  • getylamino represents a dialkylamino group such as phenyl, dipropylamino, a halogen atom such as fluorine, chlorine, or bromine, or a leaving group such as imidazolyl
  • R 7 is a lower alkyl group such as methyl, ethyl, or propyl.
  • Y represents an alkoxy group such as methoxy, ethoxy, propoxy, isopropoxy, butoxy or a dialkylamino group such as mono or dimethylamino, getylamino, dipropylamino, etc. represented.
  • H a 1 represents a halogen atom.
  • R 4 and R 5 may form a ring having 3 to 8 carbon atoms together )
  • compound (5) is obtained by reacting compound (3) with compound (4) in the presence of a base.
  • This reaction is carried out in a solvent such as hydrocarbons such as benzene, toluene, and xylene, and ethers such as diethyl ether and tetrahydrofuran (THF), in a solvent such as sodium hydride, butyllithium, and diisobutylene.
  • bases such as butyllithium amide, sodium or potassium alkoxide, and trialkylamines such as triethylamine, at a temperature ranging from -78 to the boiling point of the solvent used. It takes several minutes to several ten hours.
  • the compound (5) is reacted with the compound (6) to obtain a compound (2).
  • This reaction is carried out in hydrocarbons such as benzene, toluene, and xylene, ethers such as dimethyl ether and THF, and solvents such as DMF, DMS II, and HMPA at a temperature from 0 ° C to the boiling point of the solvent used. It takes several minutes to several 10 hours.
  • Compound (7) can be obtained by reacting compound (3) with compound (6). This reaction is carried out in hydrocarbons such as benzene, toluene, and xylene; ethers such as dimethyl ether and THF; halogenated hydrocarbons such as chloroform and dichloromethane; and solvents such as DMF, DMSO, and HMPA. It is carried out for several minutes to several ten hours at a temperature ranging from 0 ° C to the boiling point of the solvent used.
  • hydrocarbons such as benzene, toluene, and xylene
  • ethers such as dimethyl ether and THF
  • halogenated hydrocarbons such as chloroform and dichloromethane
  • solvents such as DMF, DMSO, and HMPA.
  • the obtained compound (7) and the compound (8) are reacted in the presence of a base.
  • a base such as sodium hydride or trialkylamin such as triethylamine in a solvent at a temperature ranging from 20 to the boiling point of the solvent used for several minutes to several 10 hours.
  • Specific examples of the compound (6) used in the above reaction include N, N-dimethylformamide-dimethylacetate, t_butoxybis (dimethylamino) methane, and N-formylpyrrolidinedimethyl Acetal and the like.
  • the compound (5) has ketone and enol tautomers, and the compound (2) and the compound (7) have cis and trans geometric isomers. obtain. All of these isomers can be used for producing the compound of the present invention.
  • R represents an alkyl group or a C, - representing the e ⁇ Rukokishikarubo two Le group.
  • the 4-cyanoisoxazole represented by the formula (c) reacts the acylacetonitrile represented by the formula (a) with the substituted ditolyloxide represented by the formula (b). It can be obtained by doing.
  • the reaction is carried out by halogenated hydrocarbons such as chloroform, dichloromethane, and carbon tetrachloride; hydrocarbons such as benzene, toluene, and xylene; ethers such as getyl ether and THF; methanol; and ethanol. Performed in a range of alcohol solvents from 0 ° C to the boiling point of the solvent used. It is.
  • R represents d-6 alkyl or d-6 ⁇ Rukokishikarubo two Le group, X, Z are each independently.
  • Ts represents a p-methylphenylsulfonyl group.
  • the compound represented by the formula (e) can be obtained by reacting the compound represented by the formula (c) with imidoyl chloride represented by the formula (d). In the reaction, 1 mol of the compound represented by the formula (c) and 0.5 to 2.0 mol of imidoyl chloride represented by the formula (d) are converted into 0.5 to 2.0 mol of chloride.
  • the reaction is carried out in a solvent such as benzene, 0-dichlorobenzene, dichloromethane, 1,2-dichloroethane in the presence of a Lewis acid such as aluminum, stannic chloride or zinc chloride. The reaction proceeds smoothly in a temperature range from room temperature to the boiling point of the solvent used.
  • the desired product can be obtained by performing ordinary post-treatment.
  • the structure of the compound of the present invention was determined from IR, NMR and MS.
  • the compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, etc., and has an insecticidal, nymphalidic, larvicidal and egg-killing action.
  • insecticidal, nymphalidic, larvicidal and egg-killing action The following are typical examples.
  • Lepidopteran pests for example, Spodoptera litura, Ganoderma oleracea, Tamanayaga, Aomushi, Yumanaginiba, Konaga, Chinococa Kumonhamaki, Chiyamahamaki, Momomosinkiga, Nashihime Shingui, Mikanhamagamoriga, Chiyamahogasoma , Chadokuga, Nikameiga, Kobunomeiga, Bite Corncobola-, Amerika Kashiro Hitori, Sujimadarameiga, Heliotis, Heli Koberpa, Aggrotis, Iga, Kodlinga, Membrane Mimushi etc.
  • Hemiptera pests for example, peach aphid, aphid aphid, Nisedai koa aphid, barley vilae aphid, scorpion bug, beetle mosquito, yano enemy mosquito, kukonakaya maggot, onshikonajirami, tobacco Mi, Nishigumushimushi, Tobi-iron power, Hime-to-bin power, Sedge lownka, Tsumaguro'i etc.
  • Coleopteran pests for example, Cypridinae beetle, Leaf beetle, Colorado beetle, Rice beetle, Beetle beetle, Azuki beetle, Bean beetle, Brown beetle, Jabrotica, Tobacco beetle, Hiraki beetle Origami, Agriotis spp.
  • Diptera insect pests for example, house flies, oak mouth flies, sentinia flies, perfume flies, mycophores, flies, rice flies, rice flies, flies, flies, and flies. Thailand Shima power, Shinahamadara power etc.
  • Pterodactyl pests for example, southern milk thistle, eastern milk thistle.
  • Hymenopteran pests for example, Diplomat, Yellow-winged Wasp, and Powered wasp.
  • Orthoptera pests for example, German cockroaches, American cockroaches, Black cockroaches, Tonosa ⁇ tta etc.
  • Isoptera pests for example, house termites, mountain termites and the like.
  • Lepidopteran insects for example, human fleas, louse pests, for example, human lice, mites, for example, Nami-hadani, Kanza-hadani, Mikan-mite, Lingo spider mites , Mikansavidani, Lingosavidani, Tyrannocarpus mite, Brevipalpas, Jeote tranicas, Robinne mite, Scarab mite, Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae.
  • Plant-parasitic nematodes for example, sweet potato nematode, Negusaresenchu, soybean cistocentiyu, rice singarecentiyu, matsunoza centiyu, and the like.
  • the compound of the present invention is an agent having an excellent insecticidal and acaricidal effect against not only susceptible strains but also pests of organic phosphorus, carbamate or pyrethroid-resistant strains and mites of acaricide-resistant strains. .
  • the compound of the present invention has low phytotoxicity, low toxicity to fish poisons and warm-blooded animals, and is a highly safe drug.
  • the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets.
  • the thus-obtained compound of the present invention When the thus-obtained compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be used in the form of a general pesticide for use as a pesticide. That is, they can be used in the form of wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, flowables and the like.
  • vegetable powders such as soybean grains and flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc.
  • Organic and inorganic compounds such as fine powder, sodium benzoate, urea and sodium sulfate are used.
  • petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, DMF, DMSO, alcohol, acetate, trichloroethylene, methyl
  • solvents such as chilso-septyl ketone, mineral oil, vegetable oil, and water.
  • surfactant examples include, but are not particularly limited to, alkylphenol to which polyoxyethylene is added, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, and polyester.
  • Nonionic surfactants such as sorbitan higher fatty acid esters to which polyoxyethylene has been added, trisulfuryl ether to which polyoxyethylene has been added, and sulfuric acid ester salts of alkylphenyl ether to which polyoxyethylene has been added , Alkyl benzene sulfonate, higher alcohol sulfate, alkyl naphthalene sulfonate, polycarboxylate, lignin sulfonate, formaldehyde condensate of alkyl naphthalene sulfonate, isobutylene-anhydrous maleate Copolymerization of acid And the like.
  • the amount of the active ingredient is preferably from 0.01 to 90% by weight, more preferably from 0.05 to 85% by weight.
  • the wettable powders, emulsions, suspensions, and flowables thus obtained are diluted to a predetermined concentration with water to prepare suspensions or emulsions, and powders and granules are used directly for plants. Used in a spraying method.
  • the compound of the present invention alone is sufficiently effective, but it can also be used in combination with one or more of various fungicides, pesticides or synergists.
  • fungicides insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.
  • Captan Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Propineb, Polycarbamate, Crocodon Ronil, Kind Isen, Capya Hol, Iprodione, Procymidone, Bink Rozolin, Fluoroymid, Thymoxanil, Mepronil, Flutranil, Pencyclone, Oxycarboxin, Josetylaluminium, Propamocab, Triazimehon, Triazimenol, Propiconazole, Diclob Tolazole, Vitel-Nol, Hexaconazole, Microbil-Nil, Flusilazole, Ethaconazole, Fluorotriazole, Furtriaphen, Benconazole, Giniconazole, Cyprocona Ezo's, Fenari Mall, Tri-Fulmi Sol, Prochloraz, Imazalil, Perfurazoate, Tridemorph, fenpropimorph, trifolin, pthio
  • Plant growth regulator Plant growth regulator
  • Jibere Li emissions (such Jibere Li down A 3, Jibere Li down A 4, Jibere Li down A 7), IAA s NAA and the like.
  • 4-I-tert-butylbenzylbromide 4 -tert-butylbenzylmagnesium bromide prepared from 4.34 g and 0.46 g of magnesium 4 — Cyanone 1 -methyl 1 3 — Trifluoromethylpyrazole 1.0 g of a 3 m 1 solution of getyl ether was added dropwise at 178 ° C, and after completion of the addition, the mixture was allowed to stand at room temperature overnight. After pouring the reaction solution into water, concentrated hydrochloric acid was added to dissolve insolubles.
  • nHex means n-Hexyl.
  • nHex means n-Hexyl. same as below.
  • Table 5 (continued)
  • the active ingredient 1 If the above ingredients are mixed and wet milled until the particle size becomes 1 micron or less, the active ingredient 1
  • the compound was diluted with water so that the compound concentration became 125 ppm.
  • Corn leaves were immersed in the chemical solution for 30 seconds, air-dried, and then put into a petri dish containing five third-instar larvae. They were put in a constant temperature room at a temperature of 25 ° C and a humidity of 65% with a glass lid, and the insecticidal rate was examined after 5 days. Two iterations.
  • the acaricidal effectiveness was determined by the following formula.
  • Acaricidal effectiveness (%) X 1 0 0
  • the compound represented by the formula (1) has excellent insecticidal and acaricidal activity, and the composition containing the compound of the present invention is effective as a pesticide.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract

Nouveaux composés d'isoxazole, procédé de préparation de ces composés et pesticides contenant ces composés en tant que principe actif. Ces composés sont de formule générale (1) dans laquelle A est un groupe hétérocyclique éventuellement substitué par G ou phényle éventuellement substitué par G (G étant halogéno, alkyle C1-C6, phényle éventuellement substitué ou analogue), le groupe hétérocyclique contenant thiazole etc.; B est phényle substitué par halogéno ou analogue, ou un groupe hétérocyclique (tel que pyrazol) substitué par halogéno, alkyle C1-C6 ou analogue; et R est hydrogène, alkyle C1-C6 ou analogue.
PCT/JP1998/003065 1997-07-09 1998-07-08 Composes d'isoxazole, procede de preparation desdits composes, ainsi qu'insecticides et acaricides WO1999002507A1 (fr)

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US6462049B1 (en) 1996-04-25 2002-10-08 Nissan Chemical Industries, Ltd. Ethylene derivatives and pesticides containing said derivatives
US6642234B1 (en) 1998-12-25 2003-11-04 Nissan Chemical Industries, Ltd. Acrylonitrile compounds
US7884094B2 (en) 2005-02-17 2011-02-08 Synta Pharmaceuticals Corp. Compounds for the treatment of proliferative disorders
WO2013104705A1 (fr) * 2012-01-11 2013-07-18 Bayer Intellectual Property Gmbh Composés de tétrazol-5-ylaryle et tirazol-5-ylaryle et utilisation desdits composés comme herbicides
WO2015052173A1 (fr) * 2013-10-10 2015-04-16 Basf Se Composés tétrazole et triazole et leur utilisation en tant qu'herbicides
WO2016033285A1 (fr) * 2014-08-29 2016-03-03 E. I. Du Pont De Nemours And Company Triazoles herbicides
WO2018180943A1 (fr) * 2017-03-27 2018-10-04 Ａｇｃ株式会社 Procédé de production d'acide carboxylique de pyrazole contenant un halogène et intermédiaire associé
US10443044B2 (en) 2014-04-17 2019-10-15 Ips Heart Generating cardiac progenitor cells from pluripotent stem cells using isoxazole or isoxazole like compounds

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US5256666A (en) * 1991-11-18 1993-10-26 Basf Aktiengesellschaft 3-Isoxazolylphenyl compounds, their preparation and their use
WO1996025405A1 (fr) * 1995-02-13 1996-08-22 G.D. Searle & Co. Isoxazoles substitues utilisables dans le traitement d'inflammations

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US5256666A (en) * 1991-11-18 1993-10-26 Basf Aktiengesellschaft 3-Isoxazolylphenyl compounds, their preparation and their use
WO1996025405A1 (fr) * 1995-02-13 1996-08-22 G.D. Searle & Co. Isoxazoles substitues utilisables dans le traitement d'inflammations

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BORDA J, ET AL.: "SYNTHESIS OF 4,5-DIPHENYLISOXAZOLES AND THEIR INSECTICIDAL DERIVATIVES", ACTA CHIMICA ACADEMIAE SCIENTIARUM HUNGARICA., BUDAPEST., HU, vol. 104, no. 04, 1 January 1980 (1980-01-01), HU, pages 389 - 396, XP002911168, ISSN: 0001-5407 *

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6462049B1 (en) 1996-04-25 2002-10-08 Nissan Chemical Industries, Ltd. Ethylene derivatives and pesticides containing said derivatives
USRE38188E1 (en) 1996-04-25 2003-07-15 Nissan Chemical Industries, Ltd. Ethylene derivatives and pesticides containing said derivatives
US7037880B2 (en) 1996-04-25 2006-05-02 Nissan Chemical Industries, Ltd. Ethylene derivatives and pesticides containing said derivatives
US7566683B2 (en) 1996-04-25 2009-07-28 Nissan Chemical Industries, Ltd. Ethylene derivatives and pesticides containing said derivatives
US6642234B1 (en) 1998-12-25 2003-11-04 Nissan Chemical Industries, Ltd. Acrylonitrile compounds
US7884094B2 (en) 2005-02-17 2011-02-08 Synta Pharmaceuticals Corp. Compounds for the treatment of proliferative disorders
US8269017B2 (en) 2005-02-17 2012-09-18 Synta Pharmaceuticals Corporation Compounds for the treatment of proliferative disorders
US9090603B2 (en) 2005-02-17 2015-07-28 Synta Pharmaceuticals Corporation Compounds for the treatment of proliferative disorders
US8598366B2 (en) 2005-02-17 2013-12-03 Synta Pharmaceuticals Corporation Compounds for the treatment of proliferative disorders
US20140342906A1 (en) * 2012-01-11 2014-11-20 Bayer Intellectual Property Gmbh Tetrazol-5-yl- and triazol-5-yl-aryl compounds and use thereof as herbicides
CN104024234B (zh) * 2012-01-11 2016-09-28 拜耳知识产权有限责任公司 四唑-5-基-和***-5-基-芳基化合物及其作为除草剂的用途
JP2015504891A (ja) * 2012-01-11 2015-02-16 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー テトラゾール−５−イル−およびトリアゾール−５−イル−アリール化合物ならびに除草剤としてのそれの使用
CN104024234A (zh) * 2012-01-11 2014-09-03 拜耳知识产权有限责任公司 四唑-5-基-和***-5-基-芳基化合物及其作为除草剂的用途
WO2013104705A1 (fr) * 2012-01-11 2013-07-18 Bayer Intellectual Property Gmbh Composés de tétrazol-5-ylaryle et tirazol-5-ylaryle et utilisation desdits composés comme herbicides
US9107414B2 (en) 2012-01-11 2015-08-18 Bayer Cropscience Ag Tetrazol-5-yl- and triazol-5-yl-aryl compounds and use thereof as herbicides
WO2015052173A1 (fr) * 2013-10-10 2015-04-16 Basf Se Composés tétrazole et triazole et leur utilisation en tant qu'herbicides
US10443044B2 (en) 2014-04-17 2019-10-15 Ips Heart Generating cardiac progenitor cells from pluripotent stem cells using isoxazole or isoxazole like compounds
WO2016033285A1 (fr) * 2014-08-29 2016-03-03 E. I. Du Pont De Nemours And Company Triazoles herbicides
CN106659159A (zh) * 2014-08-29 2017-05-10 杜邦公司 除草***
US10681909B2 (en) 2014-08-29 2020-06-16 Fmc Corporation Herbicidal triazoles
WO2018180943A1 (fr) * 2017-03-27 2018-10-04 Ａｇｃ株式会社 Procédé de production d'acide carboxylique de pyrazole contenant un halogène et intermédiaire associé
CN110461822A (zh) * 2017-03-27 2019-11-15 Ａｇｃ株式会社 含卤素吡唑羧酸及其中间体的制造方法
JPWO2018180943A1 (ja) * 2017-03-27 2020-02-06 Ａｇｃ株式会社 ハロゲン含有ピラゾールカルボン酸及びその中間体の製造方法

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