JP2017075125A - Thienyl isoxazole derivative and nematicide containing the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel nematicide.SOLUTION: A nematicide contains a compound represented by general formula (I) in the figure or a salt thereof as an active ingredient. (In the formula, Rrepresents a phenyl group, pyridyl group or thienyl group, where the phenyl group may have a halogen atom substituted at the para position.)SELECTED DRAWING: None

Description

  The present invention relates to a specific thienylisoxazole derivative and a nematicide containing the same as an active ingredient.

  So far, various compounds have been investigated for the purpose of controlling nematodes and are put into practical use. Among them, for example, it is disclosed that certain thienyloxadiazole compounds and thienyltetrazole compounds disclosed in Patent Documents 1 and 2 have a nematicidal effect. However, there is no description regarding the thienyl isoxazole compound in the present invention. Non-patent documents 1 to 3 describe thienylisoxazole compounds related to the present invention, but none of them describes the nematicidal activity.

International Publication No. 2009/023721 International Publication No. 2012/030887

Journal of Organic Chemistry (2014), 79 (5), 2049-2058 Heterocycles (1983), 20 (3), 501-4 Tetrahedron (1976), 32 (20), 2437-8

  In crop production such as agriculture, damage by nematodes is large, and development of new nematicides with a low dose and a broad control spectrum is desired because of the occurrence of resistance to existing drugs and reduction of environmental burden . The present invention aims to provide a compound having excellent nematicidal activity in order to meet these demands.

As a result of intensive studies to solve the above problems, the present inventors have found that thienylisoxazole, which is a compound represented by the general formula (I), has excellent performance as a nematicide, It came to complete invention. That is, the present invention
[1] General formula (I):
(In the formula, R ₁ represents a phenyl group, a pyridyl group or a thienyl group, and the phenyl group may be substituted with a halogen atom at the para position) or a nematicide containing a salt thereof as an active ingredient Insecticide,
[2] 3- (phenyl) -5- (2′-thienyl) -isoxazole, 3- (4′-fluorophenyl) -5- (2′-thienyl) -isoxazole, 3- (3′-pyridyl)- Contains at least one compound selected from the group consisting of 5- (2′-thienyl) -isoxazole and 3- (2′-thienyl) -5- (2′-thienyl) -isoxazole or a salt thereof as an active ingredient Nematicide,
[3] General formula (I):

(Wherein R ₁ represents a phenyl group, a pyridyl group or a thienyl group, and the phenyl group may be substituted with a halogen atom at the para position) or use thereof as a nematicide , Regarding.

  ADVANTAGE OF THE INVENTION According to this invention, the nematicide which shows the outstanding control effect by a low dose can be provided.

  The definition of the formula (I) of the thienyl isoxazole compound of the present invention will be described below. In the present specification, “n-” means normal, “i-” means iso, and “s-” means secondary.

  The compounds of formula (I) are shown below.

Here, R ₁ represents a phenyl group, a pyridyl group or a thienyl group. In the case of a phenyl group, a halogen atom may be substituted at the para position.

  Specifically, the phenyl group substituted with a halogen atom at the para position is a 4-fluorophenyl group, a 4-chlorophenyl group, a 4-bromophenyl group, or a 4-iodophenyl group.

The pyridyl group as R ₁ includes positional isomers such as a 2-pyridyl group and a 3-pyridyl group.

The thienyl group as R ₁ includes positional isomers such as 2-thienyl group and 3-thienyl group.

  Specific examples of the compound represented by the formula (I) include 3- (phenyl) -5- (2′-thienyl) -isoxazole, 3- (4′-fluorophenyl) -5- (2′-thienyl). ) -Isoxazole, 3- (3′-pyridyl) -5- (2′-thienyl) -isoxazole, 3- (2′-thienyl) -5- (2′-thienyl) -isoxazole.

  The thienyl isoxazole compound represented by the formula (I) of the present invention can be produced according to the methods described in known literatures (for example, Non-Patent Documents 1, 2, and 3). Specific compounds and spectral data are exemplified in Table 1, but the present invention is not limited thereto.

  In the table, NMR data “s” indicates a singlet (single line), “d” indicates a doublet (double line), “t” indicates a triplet (triple line), and “m” indicates a multiplet (multiple line).

  The nematicide containing the thienyl oxazole compound represented by the general formula (I) of the present invention as an active ingredient is suitable for controlling nematodes in soil in the field of fruit trees, vegetables, other crops and flowers. .

  Examples of nematodes to be used for the nematicide of the present invention include Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, and Meloidogyne arenaria nematode genera such as Meloidogyne arenaria. , Ditylelenchus nematodes such as Ditylelenchus destructor and Ditylelenchus dipsaci Pratylenchus nematodes such as nematodes (Pratylenchus vulnus), potato cyst nematodes (Globodera rostochiensis), potato white cyst nematodes (Globodera pallida), etc., and soy cyst nematodes (Heterodera glycines) , Heterodera nematodes such as sugar beet nematode (Heterodera shachtoii), Aphelenchoides nematodes such as Aphelenchoides ritzemabosi, Aphelenchoides fragarieae (Aphelenchus avenae) and other Aphelenchus nematodes, Radophpolus similis and other Radophpolus genus nematodes, Tylenchulus semipenetrans and other Tylenchulus genus, and Rotylenchulus reniformis Examples include, but are not limited to, Rotylenchulus nematodes and the like. Furthermore, the nematicide of the present invention is also effective for animal parasitic nematodes such as roundworms, gourds, anisakis, filariae, and scabies.

  When the compound represented by the general formula (I) is used as a nematicide, the compound represented by the general formula (I) may be used as it is, but a suitable solid carrier, liquid carrier, gaseous carrier, etc. A preparation may be prepared by mixing with a carrier, a surfactant, a dispersant, other preparation adjuvants, and the like. As the preparation, preferably, emulsion, EW agent, liquid agent, suspension agent, wettable powder, granular wettable powder, powder, DL powder, powder, granule, tablet, oil, aerosol, flowable, dry flowable Agents, microcapsules, and the like. It can be used as a dosage form arbitrarily selected as these preparations.

  Examples of the solid carrier include talc, bennite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, silica sand, silica, zeolite, perlite, attapulgite, pumice, ammonium sulfate, sodium sulfate, urea, and the like. It is done.

  Examples of the liquid carrier include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol, and propylene glycol; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; and aliphatic hydrocarbons such as n-hexane, kerosene, and kerosene. , Aromatic hydrocarbons such as toluene, xylene and methylnaphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamide, dimethylacetamide and the like Acid amides, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, water and the like.

  Examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide gas, dimethyl ether and the like.

  Examples of the surfactant and the dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, and alkyl sulfosuccinic acids. Salt, formalin condensate of alkyl naphthalene sulfonate, polycarboxylate, POE polystyryl phenyl ether sulfate and phosphate, POE / POP block polymer, and the like.

  Furthermore, examples of the adjuvant for preparation include carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyethylene glycol, liquid paraffin, calcium stearate, and antifoaming agent, preservative and the like. It is done.

  The above-mentioned various carriers, surfactants, dispersants, and formulation adjuvants can be used alone or in combination as necessary.

  The content of the compound represented by formula (I), which is an active ingredient in the preparation, is not particularly limited, but is preferably 1 to 75% by weight in the emulsion, 0.3 to 25% by weight in the powder, water It is 1 to 90% by weight in the case of a powder and 0.5 to 10% by weight in the case of a granule.

  The nematicide according to the present invention can be used as it is or after diluting it. However, other pesticides and fungicides are further used for controlling the pests to be controlled, for the expansion of the control period, or for the purpose of reducing the dose. , Acaricide, herbicide, plant growth regulator, fertilizer and the like.

  Examples of drugs that can be used together or in combination include, for example, the Pesticide Manual (issued by The 16th Edition The British Crop Protection Council) and Shibuya Index (SHIBUYA INDEX 16th Edition, 2011, published by SHIBUYA INDEX RESARCHH GROUP X Edition, 2012, published by SHIBUYA INDEX RESEARCH GROUP) and Irac mode of action classification (mode of Action Classification Version 7.3, published by IRAC), mode of action of fungion (mode of action 15) Annual version, F It includes agents according to AC issue).

  Insecticides that can be combined or used include, for example, alanycarb, aldicarb, bendiocarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxy Butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formenanate, furathiocarb, isoprocarb, methiocarb ), Mesomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, thiofanox, triazamate, trimethacarb, XMC, xylylcarb , Metorcarb (met olcarb), caromate compounds such as fenothiocarb, fenoxycarb, acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiomethone ( ethylthiometon), chlorethoxyfos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos , Cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion ( ethion), etoprophos, femme foo Famphur, fenamifos, fenitothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl = O- (methoxyaminebothiophosphoryl) ) Salicylate ([isopropyl O- (methoxyaminothiophosphoryl) salicylate]), isoxathion, malathion, mecarbam, metamidophos, methidathion, mevinphos, monocrotophos, Naled, omethoate, oxydimeton methyl, parathion, parathion-methyl, PAP, phorate, phosalone, phosmet, phosphamidone (phosphamidon), phoxim, pirimiphos Pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfosme, tebupirimfosme Terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, chlorpyrifos-methyl, disulfoton, sulfophos organophosphate compounds such as sulprofos), flupyrazophos, phenthoate, fonofos, tribufos, endosulfan, alpha-endosulfan, gamma-HCH ( gamma-HCH), dichophor (di cofol), chlordane, dieldrin, organochlorine compounds such as methoxyclor, acetoprole, fipronil, etiprole, pyrafluprole, pyriprole, pyriprole), phenylpyrazole compounds such as flufiprole, metadiamide compounds such as broflanilide, isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, acrinathrin (acrinathrin), allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl, bioresmethrin (bioallethrin S-cyclopentenyl) bioresmethrin), Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, Alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin , Empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate ( tau-fluvalinate), Halfenprox, Imipro Phosphorus (imiprothrin), cadresin (kadethrin), permethrin (phenmethrin), praothrin (prallethrin), pyrethrin (pyrethrin), resmethrin (smethafluofen), silafluofen, tefluthrin (tefluthrin), kappa -tefluthrin), phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, mettofluthrin, profluthrin, pyrethrum terrethrin , Pyrethroid compounds such as monfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, protrifenbut, and acetami Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, neonicotinoid compounds like thiamethoxam, sulfoxamine Compounds, butenolide compounds such as flupradidifurone, mesoionic compounds such as triflumezopyrim, dicloromezotiaz, spinosad, spinosram compounds such as spinetram , Abamectin, ivermectin, ivermectin, emamectin benzoate, milbemectin, lepimectin, macrolide compounds, hydroprene, quinoprene, geo Juvenile hormone-like compounds such as diofenolan, metoprene, 4-phenoxyphenoxy compounds such as pyriproxyfene, pyridine azomethine compounds such as pymetrozine, flonicamid Pyridinecarboxamide compounds such as oxazole compounds such as etoxazole, Bacillus thuringiensis and Bacillus sphaericus agents such as Bt subsp. Israelensis, Bt subsp. Aizawai, Bt subsp. Kurstaki, Bt subsp. Tenebrionis and the like Insecticidal proteins produced, insecticidal proteins produced by Bt crops corresponding to the above, thiourea compounds such as diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide Organometallic compounds such as propargite ( sulfite and diphenyl ether compounds such as propargite), diphenyl sulfone compounds such as tetradifon, chlorfenapyr, pyrrole compounds such as tralopyril, dinitro compounds such as DNOC, and bensultap (bensultap), cartap, thiocyclam, thiosultap, nereistoxin analogs such as thiosultap sodium, bistrifluron, chlorfluazuron, Diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflubenzuron, triflubenzuron benzoylurea compounds such as flumuron and bistrifluron, and thiadiazine compounds such as buprofezin. Triazole compounds such as cyromazine, chromafenozide, halofenozide, methoxyfenozide, diacylhydrazine compounds such as tebufenozide, amidine compounds such as amitraz, hydra Amidinohydrazone compounds such as hydramethylnon, naphthoquinone compounds such as acequinocyl, fluacrypyrim, pyriminostrobin, and strobilurin compounds such as flufenoxystrobin Quinazoline compounds such as fenazaquin, phenoxypyrazole compounds such as fenpyroxymate, phenoxyethylamine compounds such as pyrimidifen, pyridaben Pyridazinone compounds such as daben), tebufenpyrad, tolfenpyrad, pyrazole carboxamide compounds such as pyflubumide, hydrazine carboxamide compounds such as metaflumizone, spirodiclofen, Tetronic and tetramic acid compounds such as spirotetramat, spiromesifen, cyflumetofen, beta-ketonitrile compounds such as cyenopyrafen, and flubendiamide Anthranilic acid amide compounds such as phthalic acid amide compounds, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole Quinoxaline compounds such as quinomethionate, thiazolidinone compounds such as hexythiazox, hydrazine compounds such as bifenazate, pyridinamine compounds such as flufenerim, pyrifluquinazon Aminoquinazoline compounds, such as 6-phenoxyquinoline compounds such as flometoquin, pyridinylethylbenzamide compounds such as fluopyram, 8-chloro-N-((2-chloro-5- Sulfonamide compounds such as methoxyphenyl) sulfonyl) -6- (trifluoromethyl) imidazo [1,2-alpyridine-2-carboxamide], amidoflumet

  Other insecticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, India Indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoxymate, afidopyropen, fluhexafon, fluhexafon, oxazafen Sulfone (fluensulfone), benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate salt, metaaldehyde, ryanodine, sulfuramide ( sulfluramid), (E) -N- (1-((6-chloro Pyridin-3-yl) methyl) pyridine-2 (1H) -ylidene) -2,2,2-trifluoroacetamide, 5- (trifluoromethyl) -2- (4- (4- (trifluoromethyl)) And compounds such as phenoxy) piperidin-1-yl) pyridine. Furthermore, the nematicides according to the invention can also be mixed or used in combination with microbial pesticides such as entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

Examples of the disinfectant used include metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, and kiralaxyl. ), Offurace, furalaxyl, cyprofuram, phenylamide compounds, bupyrimate, dimethilimol, hydroxypyrimidine compounds such as ethilimol, hymexazole , Isoxazole compounds such as hydroxyisoxazole, piperidinylthiazole isoxazoline compounds such as oxathiapiprolin, isothiazolone compounds such as octhilinone, oxolinic acid Carboxylic acid type Compounds, benomyl, thiophanate-methyl, carbendazole, fuberidazole, thiabendazole, benzimidazole thiophanate compounds such as debacarb, dietofencarb N-phenyl carbamate compounds, toluamide compounds such as zoxamide, ethylaminothiazole carboxamide compounds such as ethaboxam, phenylurea compounds such as pencycuron, fluopicolide Pyridinylmethylbenzamide compounds such as diflumetorim, pyrimidineamine compounds such as bupirimate, pyrazolecarboxamide compounds such as tolfenpyrad, Benzanilide compounds such as benodanil, flutolanil, mepronil, phenyloxoethylthiophenamide compounds such as isofetamid, pyridinylethylbenzamide compounds such as fluopyram , Furan carboxamide compounds such as fenfuram, oxycarboxin, oxathiin carboxamide compounds such as carboxin, thiazole carboxamide compounds such as thifluzamide, floxapyroxado pyrazole-4-carboxa such as (fluxapyroxad), furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane Compounds, pyridinecarboxamide compounds such as boscalid, azoxystrobin, coumetoxystrobin, kresoxym-methyl, trifloxystrobin, picoxist Robin (picoxystrobin), pyraclostrobin (dimracstrobin), methoxystrobin (metominostrobin), orisatrobin (flusastrobin), pyroxystrobin (pyraoxystrobin), pyramethost Robin (pyrametostrobin), flufenoxystrobin (fenfeninstrobin), enoxastrobin (enoxastrobin), coumoxystrobin, mandestrobin, triclopyricarb (triclopyricarb), etc. Strobilurin-based compounds Oxazolidinedione compounds such as famoxadon, imidazolinone compounds such as fenamidone, benzyl carbamate compounds such as triclopyricarab, pyribencarb, and cyazofamid Cyanoimidazole compounds, sulfamoyltriazole compounds such as amisulbrom, dinitrophenylcroton compounds such as binapacryl, meptyldinocap, dinocap, fluazinam 2,6-dinitroaniline compounds such as, pyrimidinone hydrazone compounds such as ferimzone, acetic acid-fentin, fentin chloride, fentin hydroxide, Triphenyltin hydroxide (fent organic and inorganic metal compounds such as hin hydroxide, triphenyltin acetate, oxine copper, thiophene carboxamide compounds such as silthiofam, and triazololone such as amethoctrazine. Pyrimidineamine compounds, mepanipyrim, nitrapyrin, pyrimethanil, anilinopyrimidine compounds such as cyprodinil, enopyranuronic acid antibiotics such as blasticidin-S, Hexopyranosyl antibiotics such as kasugamycin, kasugamycin hydrochloride hydrate, glucopyranosyl antibiotics such as streptomycin, tetracycline antibiotics such as oxytetracycline, quinoxif Allyloxyquinoline compounds such as quinoxyfen, quinazoline compounds such as proquinazid, cyanodiolol compounds such as fludioxonil, fenpiclonil, fluoroimid, procymidone ), Iprodione, dicarboximide compounds such as vinchlozolin, phosphorothiolate compounds such as edifenphos, iprobenfos, pyrazophos, and isoprothiolane. Dithiolane compounds, propamocarb, propyl carbamate compounds such as propamocarb hydrochloride, Baci such as Bacillus subtilis (QST713, FZB24, MBI600, strain D747) lus genus and produced bactericidal proteins, and bactericidal proteins produced by the above Bt crops, terpene hydrocarbons and terpene alcohols such as extracts of Goseika Yupte, piperazines such as triforine Compounds, pyridine compounds such as pyrifenox, pyrisoxazole, pyrimidine compounds such as fenarimol, nuarimol, azaconazole, bromuconazole, diniconazole (diniconazole), dinicoazole-M (diniconazole-M), epoxiconazole, fluquinconazole, oxpoconazole, pefurazoate, difenoconazole, fenbuconazole ), Imibenconazole azole), ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, imazalil, viteltanil (bitertanol), triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriafol, microbutanil, paclobutrazol Azole compounds such as prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, aldimorph, dodemorph ( dodemorph), acetic acid Morpholine compounds such as dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pyrimorph, piperalin, fenpropidin Piperidine compounds such as spiroxamine, spiroketal amine compounds such as spirhexamine, hydroxyanilide compounds such as fenhexamid, aminopyrazolinone compounds such as fenpyrazamine, and felbum ( ferbam), metam, metasulphocarb, metiram, thiram, manzeb, maneb, maneb, zineb, zoram, polycarbamate Thiocars such as propineb, thiuram, pyributicarb Bamate dithiocarbamate compounds, glucopyranosyl antibiotics such as validamycin, mildiomycins, nucleoside antibiotics such as polyoxin, benchthiavalicarb, benchbalicarb isopropyl (benthiavalicarb-isopropyl), valifenalate, valinamide carbamate compounds such as iprovalicarb, mandelic acid amide compounds such as mandipropamid, isobenzofuranone compounds such as fthalide Compounds, pyrroloquinolinone compounds such as pyroquilone, triazolobenzothiazole compounds such as tricyclazole, cyclopropanecarboxamide compounds such as carpropamid, diclocimet (d carboxamide compounds such as iclocymet), propionamide compounds such as fenoxanil, benzothiadiazole compounds such as acibenzolar-S-methyl, and benzoisomers such as probenazole. Thiazole compounds, thiadiazole carboxamide compounds such as tiadinil, isothiazole carboxamide compounds such as isothianil, cyanoacetamide = oxime compounds such as cymoxanil, fosetyl and the like Ethyl phosphonate compounds, phthalamic acid compounds such as techlophthalam, benzotriazine compounds such as triazoxide, benzene sulfonic acid compounds such as flusulfamide, diclomezin e) pyridazinone compounds such as cyflufenamide, phenylacetamide compounds such as cyflufenamide, benzophenone compounds such as metrafenopne, benzoylpyridine compounds such as pyriofenone, and flutianil. Cyanomethylene thiazolidine compounds, 4-quinolylacetic acid compounds such as tebufloquin, fosetyl-aluminium, organophosphorus compounds such as tolclofos-methyl, echlomezole 1,2,4-thiadiazole compounds such as, trifluoroethyl carbamate compounds such as tolprocarb, Bordeaux mixture, copper acetate, basic copper sulfate, Oxy copper chloride, cupric hydroxide (cop per hydroxide), copper-based compounds such as oxine-copper, copper, inorganic compounds such as sulfur, N-halogenothioalkyls such as captan, captafol, and folpet Compounds, anilazine, chlorothalonil, dichlorophen, dichlorophen, pentachlorophenol and salts thereof, organochlorine compounds such as hexachlorobenzene, quintozene, iminotadine acetate Like (iminoctadine triacetate salt), iminoctadine albesilate, guanidine, dodine, dodin free base, guazatine, guazatine acetate salt, albesilate Guanidine compounds, anthraquinone compounds such as dithianon, Quinoxaline compounds such as quinomethionate, maleimide compounds such as fluoroimide, tolylfluanid, sulfenic compounds such as dichlofluanid, and dinobuton And cyclic dithiocarbamate compounds such as dinitrophenol compounds and dazomet. Other fungicides include dipymetitrone, pyraziflumid, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar ), Prohexadione-calcium, bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodocarb, Prothiocarb, N- (1- (2,4-dichlorophenyl) -1-methoxypropan-2-yl) -2-iodobenzamide, 3- (5-fluoro-3,3,4,4-tetra Methyl-3,4-dihydroisoquinolin-1-yl) quinoline, 3- (4,4-difluoro-3, -Dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, 3- (4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline and the like. .

  Examples of the present invention will be described in detail, but the present invention is not limited to the examples.

[Synthesis Example 1]
Synthesis of 3- (phenyl) -5- (2′-thienyl) -isoxazole (Compound 1 in Table 1) Compound 1 was synthesized as described in Non-Patent Document 1.

[Synthesis Example 2]
Synthesis of 3- (4′-fluorophenyl) -5- (2′-thienyl) -isoxazole (Compound 2 in Table 1) Compound 2 was synthesized in the synthesis method of Compound 1 described in Non-Patent Document 1, Instead, it was synthesized using 4-fluorobenzaldehyde.

[Synthesis Example 3]
Synthesis of 3- (2′-thienyl) -5- (2′-thienyl) -isoxazole (Compound 3 in Table 1) Known synthetic method (Inorganic Chemistry, 50 (12), 5417-5429; (2011) et al. ) Of 1,3-bis (2-thienyl) propane-1,3-dione (0.80 g), hydroxyamine hydrochloride (0.15 g) and sodium acetate (0.10 g) in methanol (8 ml). The reaction was stirred at reflux for 5 hours. After completion of the reaction, water was poured and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of the title compound 3- (2′-thienyl) -5- (2′-thienyl) -isoxazole as white crystals.

[Synthesis Example 4]
Synthesis of 3- (2′-thienyl) -5- (2′-thienyl) -isoxazole (Compound 4 in Table 1) Compound 4 was synthesized according to the description of Non-Patent Document 2.

[Biological test example]
Example 1 Test on root-knot nematode (immersion test)
(Preparation of reagent solution)
Compound 1 and Compound 3 are each made into a 1% solution with a mixed solution of dimethylformamide and acetone (1:10), and then diluted to a predetermined concentration (50 ppm and 5 ppm) with tap water (addition agent Aglar 5000 times added). Thus, a reagent solution was obtained.

(Test method)
From the eggplant grown on the root of the sweet potato, a solution containing the sweet potato root nematode stage 2 larvae was obtained by the Bellman method. This nematode-containing solution was dispensed into a 48-well plate at 100 μl per well (approximately 50 nematodes). Then, add the same amount of reagent solution as the nematode-containing solution, leave it at 26 ° C for 3 days, investigate the nematode's life and death under a stereomicroscope, and calculate the corrected death rate using the following formula: It was.

(Test results)
At a concentration of 50 ppm, the compounds 1 and 3 listed in Table 1 showed an insecticidal rate of 80% or more with a corrected death rate. At a concentration of 5 ppm, compounds 1 and 3 listed in Table 1 exhibited an insecticidal rate of 80% or higher with a corrected death rate.

[Example 2]
Test for root-knot nematode (soil pot test)
(Preparation of reagent solution)
Compound 1 was made into a 1% solution with a mixed solution of dimethylformamide and acetone (1:10) and then adjusted to a predetermined concentration with tap water to obtain a reagent solution.

(Test method)
10 ml of the above reagent solution was added to 200 g of sweet potato root nematode-contaminated soil (about 200 heads / 20 g soil) and mixed thoroughly. After filling this soil in a plastic cup (diameter: 9 cm, height: 5.5 cm), 15 tomato seeds (variety: strong rice life) were sown per cup and cultivated at 26 ° C. under constant temperature conditions for 14 days. Thereafter, the tomato seedlings were extracted so as not to damage the roots, and the degree of root nodule formation was investigated objectively according to the following indices. In addition, the root nodule index and the control effect were obtained from the nodule formation degree using the following calculation formula.

(Root nodule growth)
0: No lumps are formed 1: Slightly small lumps are observed 2: Large lumps are observed 3: Large lumps are observed in large numbers 4: Large lumps are continuous, lateral roots are hardly developed

The formula for calculating the root nodule index is as follows.

The formula for calculating the control effect is as follows.

(Test results)
At 500 ppm, Compound 1 showed a control effect of 70% or more.

Thus, the effect was confirmed about the compound contained in the range of Formula (I). Therefore, it is fully speculated that the effect is exerted for the range of the compound of the formula (I).

Claims (3)

Formula (I):
(In the formula, R ₁ represents a phenyl group, a pyridyl group or a thienyl group, and the phenyl group may be substituted with a halogen atom at the para position) or a nematicide containing a salt thereof as an active ingredient Insecticide.   3- (phenyl) -5- (2′-thienyl) -isoxazole, 3- (4′-fluorophenyl) -5- (2′-thienyl) -isoxazole, 3- (3′-pyridyl) -5- ( Line killing containing at least one compound selected from the group consisting of 2'-thienyl) -isoxazole and 3- (2'-thienyl) -5- (2'-thienyl) -isoxazole or a salt thereof as an active ingredient Insecticide. Formula (I):
(Wherein R ₁ represents a phenyl group, a pyridyl group or a thienyl group, and the phenyl group may be substituted with a halogen atom at the para position) or use thereof as a nematicide .