Pyrazole compound and agricultural or horticultural germicide

Abstract

A pyrazole compound represented by formula (Z-I) (in the formula: Q1 represents a 5- or 6-membered heterocyclyl group or the like; Q2 represents a phenyl group or the like; R1 represents a C1-6 alkyl group or the like; R2 represents a hydrogen atom, a C1-6 alkyl group, or the like; Za represents an oxygen atom or a sulfur atom; Z represents an oxygen atom or a sulfur atom; R6 represents a hydrogen atom, a C1-6 alkyl group, or the like; V represents an oxygen atom or a group represented by the formula C(R7)(R8); R7 and R8 each represent a hydrogen atom, a C1-6 alkyl group, or the like; R4 and R5 each independently represent a hydrogen atom, a C1-6 alkyl group, or the like; and n represents an integer of 0-3).

Description

Pyrazole compounds and fungicides for agriculture and horticulture

[0001] The present invention relates to pyrazole compounds and fungicides for agricultural and horticultural use. More specifically, the present invention relates to pyrazole compounds that have excellent fungicidal activity against pathogenic fungi affecting agricultural and horticultural plants, are highly safe, and can be synthesized industrially advantageously, and to fungicides for agricultural and horticultural use containing the same as an active ingredient. This application claims priority based on Japanese Patent Application No. 2024-166137 filed in Japan on September 25, 2024, Japanese Patent Application No. 2024-185251 filed in Japan on October 21, 2024, Japanese Patent Application No. 2024-202631 filed in Japan on November 20, 2024, and Japanese Patent Application No. 2025-008070 filed in Japan on January 20, 2025, the contents of which are incorporated herein by reference.

[0002] Various compounds with fungicidal activity against pathogens affecting agricultural and horticultural plants have been proposed. For such compounds to be used as fungicides in agriculture and horticulture, they must not only be sufficiently effective, but also resistant to pesticide development, not cause phytotoxicity to plants or soil contamination, and have low toxicity to livestock and fish.

[0003] Incidentally, Patent Document 1 discloses a compound represented by formula (A), etc.

[0004]

[0005] Patent document 2 discloses a compound represented by formula (B), etc.

[0006]

[0007] International Publication No. 2023 / 243678, International Publication No. 2024 / 204842

[0008] The object of the present invention is to provide a pyrazole compound that has excellent fungicidal activity against pathogenic fungi affecting agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously, as well as an agricultural and horticultural fungicide containing the same as an active ingredient.

[0009] As a result of intensive studies to solve the above problems, the present invention including the following forms has been completed. (1) A compound represented by formula (Z-I) or a salt thereof.

[0010]

[0011] [In the above formula (Z-I), Q １ represents a substituted or unsubstituted 5- or 6-membered heterocyclic group, or a substituted or unsubstituted 9- or 10-membered heterocyclic group, Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclic group, or a substituted or unsubstituted 9- or 10-membered heterocyclic group, R １ represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group, R ２ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a cyano group, or a halogeno group, Z ａ represents an oxygen atom or a sulfur atom, Z represents an oxygen atom or a sulfur atom, R ６ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5- or 6-membered heterocyclic group, V represents an oxygen atom, or a group represented by the formula: C(R ７ )(R ８ ), R ７ represents a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclic group, or a halogeno group, R ８R represents a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group. ４ Each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group, R ５ Each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group, and R on the same carbon atom ４ and R ５ (1) The compound or a salt thereof described in (1) above, wherein the (Z-I) is represented by formula (I).

[0012]

[0013] [In the above formula (I), Q １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ , R ７ , R ８ and n are Q in the above formula (Z-I). １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R６ , R ７ , R ８ And has the same meaning as n. ] (3) The compound or salt thereof described in (1) above, in which formula (Z-I) is represented by formula (Ia).

[0014]

[0015] [In the above formula (Ia), Q １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ and n are Q in the above formula (Z-I). １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ And has the same meaning as n. ] (4) The compound represented by formula (I) is one of the compounds listed in Table 1 below, the compound or a salt thereof as described in (2) above.

[0016]

[0017] (5) The compound represented by formula (I) is one of the compounds listed in Table 2 below, the compound or a salt thereof as described in (2) above.

[0018] (6) The compound represented by formula (Ia) is one of the compounds listed in Table 3 below, the compound or a salt thereof as described in (3) above.

[0019]

[0020] (7) The compound represented by formula (Ia) is one of the compounds listed in Table 4 below, the compound or a salt thereof as described in (3) above.

[0021] (8) A fungicide for agricultural and horticultural use containing at least one selected from the group consisting of the compounds and salts described in any one of (1) to (3) above as an active ingredient. (9) The fungicide for agricultural and horticultural use described in (8) above, for seed treatment. (10) The fungicide for agricultural and horticultural use described in (8) or (9) above, further containing other active ingredients. (11) The aforementioned other active ingredients include nucleic acid biosynthesis inhibitors, mitosis inhibitors, cell division inhibitors, respiratory inhibitors, amino acid and protein synthesis inhibitors, signal transduction inhibitors, lipid and cell membrane synthesis inhibitors, cell membrane sterol biosynthesis inhibitors, cell wall synthesis inhibitors, melanin biosynthesis inhibitors, host plant resistance inducers, multi-site agents, biologics with multiple mechanisms of action, acetylcholinesterase inhibitors, GABAergic chloride ion channel blockers, sodium channel modulators, nicotinic acetylcholine receptor competitive modulators, nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators, juvenile hormone analogs, nonspecific inhibitors, treble organ TRPV channel modulators, mite growth inhibitors, and microbial-derived insect midgut endometrium disruptors. A fungicide for agricultural and horticultural use according to (10), which is at least one selected from the group consisting of agents, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncoupling agents that disrupt the proton gradient, nicotinic acetylcholine receptor channel blockers, chitin biosynthesis inhibitor type 0, chitin biosynthesis inhibitor type 1, molting inhibitors, molting hormone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complex III inhibitors, mitochondrial electron transport chain complex I inhibitors, voltage-gated sodium channel blockers, acetyl-CoA carboxylase inhibitors, mitochondrial electron transport chain complex IV inhibitors, mitochondrial electron transport chain complex II inhibitors, ryanodine receptor modulators, choroid organ modulators with unspecified target sites, and GABAergic chloride ion channel allosteric modulators. (12) The other active ingredients are: Benalaxyl, Benalaxyl-M, Flalaxyl, Metalaxyl, Metalaxyl-M, Oxadixyl, Clodilacon, Offlace; Bupirimate, Dimethyrimol, Ethyrimol;Himexazole, Octylinone; Oxolinic acid; Ibuflufenokine, Quinofumeline; Benomyl, Carbendazim, Chlorphenazole, Fuberidazole, Thiabendazole, Thiophanate, Thiophanate-methyl, Dietofencarb, Zoxamide, Etaboxam; Pencyclon; Fluopicolide, Fluopimomide; Phenamacryl, Metraphenone, Pyriophenone; Pyridaclomethyl; Diflumetrim, Tolfenpyrad, Phenazaquine; Benodanil, Flutolanil, Mepronil, Isofetamide, Fluopyram, Cyclobtrifluram, Fenflam, Flumecyclox, Carboxyne, Oxycarboxyne, Tifluzamide, Benzovindiflupir, Bixafen, Fluxapyroxad, Flamethopyr, Isopyrazam, Penflufen, Penthiopyrad, Sedaxane, Boscalid, Pidiflumetofen, Isoflucipram, Pyraziflumid, Impilfluxam; Azoxystrobin, chemoxystrobin, cmethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyramethostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidomone, pyribencarb, methyltetraprole, mandestrobin; cyazofamide, amisulbrom, fenpicoxamide, florylpicoxamide; binapacril, meptyldinocap, dinocap, fluazinam; fentin acetate, fentin chloride, fentin hydroxide; silthiofame; ametoctrazine; andprim, cyprodinil, mepanipyrim, pyrimethanil; Blastosisin-S, Kasugamycin, Kasugamycin hydrochloride, Streptomycin, Oxytetracycline; Tababolol; Quinoxifen, Proquinazide; Fenpiclonil, Fludioxonil, Clozolinate, Dimethacron, Iprodione, Procymidone, Vinclozoline; Edifenfos, Iprobenfos, Pyrazofos, Isoprothiolane;Biphenyl, Chloroneb, Dichloran, Quintozene, Technazen, Torclophosmethyl, Etridiazole; Iodocarb, Propamocarb, Propamocarb Hydrochloride, Propamocarb Focetilate, Prothiocarb; Tea Tree Extract; Natamycin; Triforine, Pyriphenox, Pyrisoxazole, Fenalimol, Flurprimidol, Nualimol, Imazalil, Imazalil Sulfate, Oxpoconazole, Oxpoconazole Fumarate, Pefurazoate, Prochloraz, Triflumizole, Viniconazole, Azaconazole, Vitertanol, Bromuconazole, Cyproconazole, Diclobutrazol, Difenoconazole, Diniconazole, Diniconazole-M, Epoxyconazole, Etaco Nazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, mycrobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; Algimorph, Dodemorph, Dodemorph Acetate, Fenpropimorph, Tridemorph, Fenpropidine, Piperalin, Spiroxamine; Fenhexamide, Fenpyrazamine; Pyributicarb, Naftifine, Terbinafine; Polyoxin, Polyoxorim; Dimethomorph, Flumorph, Pyrimorph, Benciavaricarb, Benciavaricarb Isopropyl, Iprovalicarb, Valifenarate, Mandipropamide; Phusalide, Pyrroquilon, Tricyclazole; Carpropamide, Diclocimet, Phenoxanil; Tolprocarb; Acibenzolar-S-methyl, Probenazole, Thiazinyl, Isothianil, Diclobentiazox; Ipfentrifluconazole, Laminarin, Polygonum cuspidatum Extract; Fosetyl aluminum, fosetyl calcium, fosetyl sodium, phosphoric acid, phosphate, phosphorous acid, phosphate;Cymoxanil, tecrophthalam, triazoxide, fursulfamide, diclomedin, cyflufenamide, dozin, dozin free base, fluthianil, ferimzon, tebufloxin, picarbtrazox, validamycin; copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ambam, farbam, mancozeb, maneb, mancapper, methylam, methylam zinc, polycarbamate, propineb, thyram, zineb, zillam; captan, captafoll, forpet, chlorothalonil, diclofluanide, tolfluanide, guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine trialbesylate, anilazine, dithianone, quinomethionate, fluorimide, metasulfocarb; DBEDC, Fluorofolpet, Bis(8-Quinolinolate)copper(II), Propamidine, Chloropicrin, Cyproflam, Agrobacterium, Bethoxazine, Diphenylamine, Methylisothiocyanate (MITC), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumetobel, Irmamycin, Nitrotar Isopropyl, Oxamocarb, Pyrrolenitrin, Torniphanide, Zarilamid, Algophase, Amicalthiazole, Oxathiapiproline, Fluoxapiproline, Benzazole, Triclamide, Uniconazole, Oxyphenthiin, Pirapropoin, Fluindapyr, Aminopyrifene, Dipimethitrone, Fluphenoxadiazam, Flumethylsulforim, Feneptamidocine; Trichoderma atroviride I-1237 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride LU132 strain, Trichoderma atroviride SC1 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride 77B strain; Trichoderma aspererum T34 strain, Trichoderma aspererum kd strain; Trichoderma halzianum T-22 strain; Trichoderma virens G-41 strain; Chronostachys rosea J1146 strain, Chronostachys rosea CR-7 strain; Coniothirium minitans CON / M / 91-08 strain;Hanseniaspora ubaram BC18Y strain; Talaromyces flavus SAY-Y-94-01 strain; Saccharomyces cerevisiae LAS02 strain, Saccharomyces cerevisiae DDSF623 strain; Bacillus amyloriquefaciens QST713 strain, Bacillus amyloriquefaciens FZB24 strain, Bacillus amyloriquefaciens MBI600 strain, Bacillus amyloriquefaciens D747 strain, Bacillus amyloriquefaciens F727 strain, Bacillus amyloriquefaciens Bacillus subtilis strain AT-332; Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404, Bacillus subtilis strain RTI477; Bacillus berezensis strain RTI301; PHC25279; Gluconobacter serinas strain BC18B; Pseudomonas chlororaffis strain ASF009; Pseudomonas rhodesia strain HAI-0804; Streptomyces griseobilides strain K61, Streptomyces riddix strain WYEC108; Alanicarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimicarb, Propoxul, Thiodicarb, Thiofanox, Triazamate, Trimetacarb, XMC, Xylylcarb; Phenothiocarb, MIPC, MPMC, MTMC, Aldoxycarb, Alixicarb, Aminocarb, Bufencarb, Chloetocarb, Metam sodium, Promecarb;Acephate, Azamethiphos, Adinphos-ethyl, Adinphos-methyl, Kazsaphos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos, Diclotophos, Dimethoate, Dimethylvinphos, Disulfon, EPN, Ethion, Etoprophos, Fanflu, Phenamiphos, Fenitrothion, Fenthion, Fostiazate, Heptenophos, Imisiaphos, Isofenphos, Isocarbophos, Isopropyl-O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Metamidophos, Methidathion, Mevinphos, Monoclotophos, Nared, Omethoate, Oxydimethone-methyl, Parathion, Para Thione methyl, fenthoate, phorate, fosalon, fosmet, phosphamidone, foxim, pyrimiphos methyl, profenofos, propetamfos, prothiofos, pyraclofos, pyridaphenthion, quinalfos, sulfotep, tebupyrimfos, temefos, terbufos, tetrachlorvinfos, thiometon, triazofos, trichlorfon, bamidothion, bromophos ethyl, BRP, carbophenothion, cyanophenfos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, honofos, formothion, fosmetylane, isazofos, iodophenfos, methacryfos, pyrimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos; Chlordane, endosulfan, ethiprole, fipronil; acetoprole, pyrafluprole, pyriprole, campechlor, heptachlor, dienochlor, flufiprol;Acrinatrin, allethrin, d-cistrans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, biorethmetrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin Lumethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, cadesrin, permethrin, phenothrin Phosphorus [(1R)-trans isomer], prallethrin, pyrethram, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioetanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metofluthrin, protrefenbut, pyrethmethrin, terarethrin, κ-bifenthrin, chloroprarethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioetanomethrin; DDT, Methoxychlor; Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Nichiazine, Thiacloprid, Thiamethoxam, Nicotin, Sulfoxaflor, Flupyradiflon, Dichloromesothiaz, Fenmesoditiaz, Triflumesopyrim, Flupyrimin; Spinetoram, Spinosad; Abamectin, Emamectin, Emamectin Benzoate, Lepimectin, Milbemectin; Ivermectin, Selamectin, Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin, Milbemycin, Milbemycin Oxime, Nemadectin;Hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen; diofenolane, epophenonane, triprene; 1,3-dichloropropene, methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartaric acid, dazomet, metam, potassium metam, sodium metam; pymetrozine, pyrifluquinazone, afidopiropene; clofentezine, diflovidazine, hexythiazox, etoxazole; Proteins contained in Bacillus thuringiensis subspecies islaerensi, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies krustachi, Bacillus thuringiensis subspecies tenebryonis, Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus; diafenthiurone, azocyclotin, cyhexatin, fenbutasin oxide, propargit, tetradiphon; chlorfenapyr, DNOC, sulfuramide; binapacril, dinobton, dinocap; Bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt; nereistoxin; bistriflurone, chlorfluazurone, diflubenzuron, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, nobiflumuron, teflubenzuron, triflumuron; buprofezin, fluazurone; buprofezin; cilomazine; chromafenozide, halofenozide, methoxyfenozide, tebufenozide; amitraz; demiditraz, chlordimeform; hydramethylnon, acequinosyl, fluacrypyrim, bifenazate; phenazaquine, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; indoxacarb, metaflumizone; Spidoxamat, spirodiclofen, spiromesifen, spiropidione, spirotetramat;Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide; cyenopyrafen, cyflumetofen, piflubmid; chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodianide, tetraniliprole; tetrachlorantraniliprole; flonicamide; fluxamethamide, isocycloceram, broflanilide; afoxolaner, fluralaner, rotineral, sarolaner; acinonapir, flomethkin, redoprona, zinpropyridaz, oxazosulfyl, azadirachtin, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, dicofol, lime sulfur mixture, mancozeb, pyridaryl, sulfur; Cryolite, Bencrothiaz, Amidoflumet, DCIP, Phenisobromolate, Benzomate, Metaldehyde, Chlorbenzilate, Clothiazoben, Dicyclanil, Phenoxacrim, Fentriphanil, Flubenzimine, Fluphenazine, Gossiplua, Japonilua, Methoxadiazone, Petroleum (oil), Potassium Oleate, Tetrasul, Triaracene, Afidopiropene, Flufiprol, Fluensulfol Meperflusrin, tetramethylflusrin, tralopyril, dimeflusrin, methylneodecanamide, broflanilide, Steiner's nema capocapsae, Steiner's nema glacerai, Pastouria penetrans, Pechylomyces stenuipes, Pechylomyces phmosoroseus, Beauveria bassiana, Beauveria bronniati, Metallidium anisoplie, Verticillium lecani, fulhexaphon, cyclopyrazoflor; Fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambendazole; closantel, oxyclozanide, lafoxanide, niclosamide; nitroxynil, nitroscanate; pyrantel, morantel; levamisol, tetramisol; praziquantel, epsiplantel;Cyclodiene, Lianya, Chlorthrone, Metronidazole, Demiditraz, Piperazine, Diethylcarbamazine, Dichlorophene, Monepantel, Tribendimidine, Amidantel, Thiacetalthamide, Melalsomine, Arsenamide; Abscisic acid, Kinetin, Benzylaminopurine, 1,3-Diphenylurea, Forchlorfenuron, Thidiazuron, Chlorfenuron, Dihydrozeatin, Gibberellin A, Gibberellin A4, Gibberellin A7, Gibberellin A3, 1-Methylcyclopropane, N-Acetylaminoethoxyvinylglycine (also known as Abiglycin), Aminooxyacetic acid, Silver nitrate, Cobalt chloride, IAA, 4-CPA, Cloprop, 2,4-D, MCPB, Indole-3-butyric acid, Dichlorprop, Phenothiol, 1-Naphthylacetamide, Ethicloze A fungicide for agricultural and horticultural use as described in (10), which is at least one selected from the group consisting of chlormecoat, cloxifonac, maleate hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobancol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, etephon, chlormecoat, mepicote chloride, benzyladenine, 5-aminolevulinic acid, and daminozide. (13) A compound represented by formula (im-3A) or a salt thereof.

[0022]

[0023] [In the above formula (im-3A), Q １ａ R represents a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted thiazolyl group. １ R represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group. ２ [where is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a cyano group, or a halogeno group, and U is a halogeno group, a hydroxyl group, or a C1-6 alkoxy group.]

[0024] The pyrazole compounds of the present invention have excellent fungicidal activity against pathogenic fungi that affect agricultural and horticultural plants, are highly safe, and can be synthesized industrially advantageously. The fungicides of the present invention can effectively control diseases of agricultural and horticultural plants.

[0025] The pyrazole compound according to one embodiment of the present invention is a compound represented by formula (Z-I) (hereinafter sometimes referred to as compound (Z-I)) or a salt of compound (Z-I).

[0026]

[0027] In this embodiment, the term "unsubstituted" means that only the core group is present. When the term "substituted" is not used and only the name of the core group is given, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that one of the hydrogen atoms of the core group is substituted with a group (substituent) that has the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. There may be one substituent or two or more substituents. The two or more substituents may be the same or different. Terms such as "C1-6" indicate that the core group has 1 to 6 carbon atoms, etc. This number of carbon atoms does not include the number of carbon atoms in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group. Substituents are chemically acceptable and are not particularly limited insofar as they have the effects of the present invention.

[0028] The following are examples of groups that can become "substituents": C1-6 alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, and n-hexyl group; C2-6 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, and 2-methyl-2-propenyl group; C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, and 1-methyl-2-propynyl group;

[0029] C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; aryl groups such as phenyl, tolyl, xylyl, trimethylphenyl, and naphthyl groups; phenyl C1-6 alkyl groups such as benzyl and phenethyl groups; 3-6 member heterocyclyl groups; 3-6 member heterocyclyl C1-6 alkyl groups;

[0030] Hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propenyloxy, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; phenoxy and naphthoxy groups; phenyl C1-6 alkoxy groups such as benzyloxy and phenethyloxy groups; 5-6 member heteroaryloxy groups such as thiazolyloxy and pyridyloxy groups; 5-6 member heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy and pyridylmethyloxy groups;

[0031] Formyl group; C1-6 alkylcarbonyl groups such as acetyl group and propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group and propionyloxy group; Benzoyl group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group; C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, and t-butoxycarbonyloxy group; Carboxylate group;

[0032] Halogeno groups such as fluoro, chloro, bromo, and iod groups; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, and perfluoro-n-pentyl groups; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl and 2-fluoro-1-butenyl groups; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, and 5-bromo-2-pentynyl groups; C1-6 haloalkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, and 2,3-dichlorobutoxy groups; C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy and 3-bromobutenyloxy groups; C1-6 haloalkylcarbonyl groups such as chloroacetyl, trifluoroacetyl, and trichloroacetyl;

[0033] Amino groups; C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, and diethylamino group; anilino group, naphthylamino group; phenyl C1-6 alkylamino groups such as benzylamino group and phenethylamino group; formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, and i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, and i-propoxycarbonylamino group; unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, and N-phenyl-N-methylaminocarbonyl group; imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, and (1-imino)-n-propyl group; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as N-hydroxyiminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxyiminomethyl group, (1-(N-methoxy)-imino)ethyl group; aminocarbonyloxy groups; C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy group and dimethylaminocarbonyloxy group;

[0034] Mercapto groups; C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and t-butylthio; C1-6 haloalkylthio groups such as trifluoromethylthio and 2,2,2-trifluoroethylthio; phenylthio and naphthylthio; 5-6 member heteroarylthio groups such as thiazolylthio and pyridylthio;

[0035] C1-6 alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl, and t-butylsulfinyl groups; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl and 2,2,2-trifluoroethylsulfinyl groups; phenylsulfinyl groups; 5-6 membered heteroarylsulfinyl groups such as thiazolylsulfinyl and pyridylsulfinyl groups;

[0036] C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, and t-butylsulfonyl group; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; phenylsulfonyl group; 5-6 membered heteroarylsulfonyl groups such as thiazolylsulfonyl group and pyridylsulfonyl group; C1-6 alkylsulfonyl groups such as methylsulfonyloxy group, ethylsulfonyloxy group, and t-butylsulfonyloxy group; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy group and 2,2,2-trifluoroethylsulfonyloxy group;

[0037] TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; triphenylsilyl; cyano; and nitro groups.

[0038] Furthermore, in these "substituents," any hydrogen atom in the substituent may be substituted with a group of a different structure. Examples of such "substituents" include C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups, halogeno groups, cyano groups, and nitro groups.

[0039] Furthermore, the above-mentioned "3-6 membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. The heterocyclyl group may be monocyclic or polycyclic. In a polycyclic heterocyclyl group, at least one ring may be heterocyclic, and the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic rings. Examples of "3-6 membered heterocyclyl groups" include 3-6 membered saturated heterocyclyl groups, 5-6 membered heteroaryl groups, and 5-6 membered partially unsaturated heterocyclyl groups.

[0040] Examples of "3-6 member saturated heterocyclyl groups" include azilidinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group.

[0041] Examples of "5-membered heteroaryl groups" include pyrrolyl, furyl, thienyl, imidazolinyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolinyl, isothiazolyl, triazolyl, oxadiazolinyl, thiadiazolinyl, and tetrazolinyl groups. Examples of "6-membered heteroaryl groups" include pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, and triazinyl groups. Examples of "5- to 6-membered partially unsaturated heterocyclyl groups" include pyrrolinyl, dihydrofuranyl, dihydrothiophenyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, and isothiazolinyl groups; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl.

[0042] Q in equation (Z-I) １ Q in formula (Z-I) represents a substituted or unsubstituted 5-6 membered heterocyclyl group, or a substituted or unsubstituted 9-10 membered heterocyclyl group. １ A substituted or unsubstituted 5-6 membered heterocyclyl group is preferred.

[0043] Q in equation (Z-I)２ Q in formula (Z-I) represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a substituted or unsubstituted 9-10 membered heterocyclyl group. ２ A substituted or unsubstituted phenyl group is preferred.

[0044] A heterocyclyl group contains at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur atoms as a constituent atom of the ring. A heterocyclyl group may be monocyclic or polycyclic. In a polycyclic heterocyclyl group, at least one ring may be heterocyclic, and the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic rings.

[0045] Q １ Or Q ２ Examples of "5-6 membered heterocyclyl groups" in this context include 5-6 membered saturated heterocyclyl groups, 5-6 membered heteroaryl groups, and 5-6 membered partially unsaturated heterocyclyl groups. １ Or Q ２ In this context, a 5-6 membered heterocyclyl group is preferred.

[0046] Q １ Or Q ２ Examples of "5-6 member saturated heterocyclyl groups" in this context include pyrrolidinyl group, tetrahydrofuranyl group, tetrahydropyranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group.

[0047] Q １ Or Q ２ Examples of "five-membered heteroaryl groups" in this context include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.

[0048] Q １ Or Q ２Examples of "six-membered heteroaryl groups" in this context include pyridyl groups, pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, and triazinyl groups. Q １ Or Q ２ In this context, a pyridyl group is preferred as the "six-membered heteroaryl group".

[0049] Q １ Or Q ２ Examples of "5- to 6-membered partially unsaturated heterocyclyl groups" in this context include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, and isothiazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl group.

[0050] Q １ Or Q ２ Examples of "9-membered heterocyclyl groups" in this context include indolyl groups, isoindolyl groups, benzofuranyl groups, benzothienyl groups, indazolyl groups, benzimidazolyl groups, benzoxazolyl groups, benzoisoxaozolyl groups, benzothiazolyl groups, benzoisothiazolyl groups, and benzodioxolanyl groups.

[0051] Q １ Or Q ２ Examples of "10-membered heterocyclyl groups" in this context include quinolinyl groups, isoquinolinyl groups, synnolinyl groups, phthalazinyl groups, quinazolinyl groups, and quinoxalinyl groups.

[0052] Among these, Q １ It is preferably a substituted or unsubstituted 5-6 membered heteroaryl group, more preferably a substituted or unsubstituted thiazolyl group, or a substituted or unsubstituted pyridyl group.

[0053] Among these, Q ２It is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted six-membered heteroaryl group, or a substituted or unsubstituted nine-membered heteroaryl group; more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted benzothiazolyl group; and even more preferably a substituted or unsubstituted phenyl group.

[0054] Q １ Or Q ２ Substituents on the "5-6 membered heterocyclyl group" or "9-10 membered heterocyclyl group" in the above include: halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkoxy group substituted with a C1-6 alkoxy group, C1-6 alkylcarbonyl group, C1-6 alkylthio group, C1-6 alkylsulfonyl group, C3-6 cycloalkyl group, phenyl group, phenyloxy group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group, nitro group, triC1-6 alkylsilyl group; amino group substituted with a C1-6 alkyl group or C1-6 alkylcarbonyl group; carboxamide group substituted with a C1-6 alkyl group; phenyl group substituted with one or more substituents of a C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; A five-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred; or a six-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred. Q １ Or Q ２More preferably, substituents on the "5-6 membered heterocyclyl group" or "9-10 membered heterocyclyl group" in the above are halogeno groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 alkylthio groups, C3-6 cycloalkyl groups, 5 membered heteroaryl groups, and amino groups substituted with C1-6 alkyl groups.

[0055] Among these, Q １ However, when it is a substituted thiazolyl group, a C1-6 haloalkyl group is preferred as the substituent on the "thiazolyl group". Q １ However, when it is a substituted pyridyl group, the substituent on the "pyridyl group" is preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, or an amino group substituted with a C1-6 alkyl group.

[0056] Q ２ However, when it is a substituted phenyl group, preferred substituents on the "phenyl group" are halogeno groups, C1-6 alkyl groups, C1-6 alkoxy groups, 5-membered heteroaryl groups, cyano groups, and amidoxime groups. Q １ However, when it is a substituted pyridyl group, the substituents on the "pyridyl group" are preferably halogen groups, C1-6 alkyl groups, and C1-6 alkoxy groups.

[0057] Q １ Or Q ２ Two substituents on the "5-6 membered heterocyclyl group" or the "9-10 membered heterocyclyl group" may combine to form a divalent organic group. Examples of divalent organic groups include C3-6 alkylene groups such as trimethylene groups and tetramethylene groups; and C1-3 alkyleneoxy groups such as methylenedioxy groups and dimethyledioxy groups.

[0058] Q ２The substituents on the "phenyl group" or "naphthyl group" in are preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkoxy group substituted with a C1-6 alkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C3-6 cycloalkyl group, a phenyl group, a phenyloxy group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a cyano group, a nitro group, a tri-C1-6 alkylsilyl group, an amidoxime group; an amino group substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group; a carboxamide group substituted with a C1-6 alkyl group; a phenyl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

[0059] Q ２ In the two substituents on the "phenyl group" or "naphthyl group" may combine together to form a divalent organic group. Examples of the divalent organic group include C3-6 alkylene groups such as a trimethylene group and a tetramethylene group; C1-3 alkylenedioxy groups such as a methylenedioxy group and a dimethylenedioxy group.

[0060] R １ represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, preferably a substituted or unsubstituted C1-6 alkyl group. R １ is preferably a substituted or unsubstituted C1-6 alkyl group.

[0061] R １ The "C1-6 alkyl group" in may be linear or branched. R１ Examples of the "C1-6 alkyl group" in [description] include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group, etc. R １ In [description], the "C1-6 alkyl group" is preferably a t-butyl group.

[0062] R １ Examples of the "C3-6 cycloalkyl group" in [description] include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.

[0063] R １ In [description], examples of the substituent on the "C1-6 alkyl group" include a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group, a hydroxyl group, a C1-6 alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group, a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, a trifluoromethoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, a cyano group; a phenyl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. Among them, any one or more of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group are more preferable.

[0064] R １Preferably, the substituents on the "C3-6 cycloalkyl group" in the above are a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, or a cyano group; a phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, with a halogeno group being more preferred.

[0065] R ２ R represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a cyano group, or a halogen group. ２ A hydrogen atom is preferred. ２ In this context, the "C1-6 alkyl group" is R １ The same examples given in [reference] can be cited. ２ Examples of "halogeno groups" in this context include fluoro groups, chloro groups, bromo groups, and iod groups.

[0066] Z in equation (Z-I) ａ represents an oxygen atom or a sulfur atom. Z in formula (Z-I) ａ An oxygen atom is preferred.

[0067] Z represents an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0068] R ６This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group.

[0069] R ６ In this context, "substituted or unsubstituted C1-6 alkyl groups" and "substituted or unsubstituted C3-6 cycloalkyl groups" are, １ The same examples given in the previous section can be cited.

[0070] R ６ Examples of "C2-6 alkenyl groups" in this context include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.

[0071] R ６ Examples of "C2-6 alkynyl groups" in this context include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, and 1,1-dimethyl-2-butynyl group.

[0072] R ６ Examples of "C1-6 alkylcarbonyl groups" in this context include acetyl group, propionyl group, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, and t-butylcarbonyl group.

[0073] R ６ Examples of "C1-6 alkoxycarbonyl groups" in this context include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group.

[0074] R ６ Substituents on the "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkylcarbonyl group", and "C1-6 alkoxycarbonyl group" include halogen groups such as fluoro, chloro, bromo, and iod groups; C1-6 alkoxy groups such as hydroxyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C3-6 cycloalkyl groups, phenyl groups, 5-membered heteroaryl groups, 6-membered heteroaryl groups, and cyano groups; and phenyl groups substituted with one or more substituents of any of the C1-6 alkyl groups, C1-6 alkoxy groups, halogen groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups. A five-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a six-membered heteroaryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred, and one or more substituents of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group are more preferred.

[0075] R ６In this context, a "5-6 membered heterocyclyl group" is a group that contains one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as constituent atoms of the ring. When there are two or more heteroatoms, they may be the same or different. Examples of a "5-6 membered heterocyclyl group" include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group; pyrrolidyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; and dihydropyranyl group, with pyrazolinyl group being preferred.

[0076] R ６ Substituents on the "phenyl group", "naphthyl group", and "5-6 membered heterocyclyl group" in the above include: halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; phenyl group substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 5-membered heteroaryl group substituted with one or more substituents of any C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; or A 6-membered heteroaryl group substituted with one or more substituents from among a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred, and a halogeno group is more preferred.

[0077] Among these, R ６ The group is preferably a hydrogen atom or a substituted or unsubstituted C1-6 alkylcarbonyl group, and more preferably a hydrogen atom.

[0078] In formula (Z-I), V is an oxygen atom, or formula: C(R ７ )(R ８ This indicates the group represented by ). ７R represents a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group. ８ This represents a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group.

[0079] R ７ and R ８ Examples of "halogeno groups" in this context include fluoro groups, chloro groups, bromo groups, and iod groups. ７ and R ８ In this context, "C1-6 alkyl groups", "substituted or unsubstituted C2-6 alkenyl groups", "substituted or unsubstituted C2-6 alkynyl groups", "substituted or unsubstituted C3-6 cycloalkyl groups", "substituted or unsubstituted phenyl groups", "substituted or unsubstituted naphthyl groups", and "substituted or unsubstituted 5-6 membered heterocyclyl groups" are as follows: １ and R ６ The same examples given in the previous section can be cited.

[0080] Among these, R ７ and R ８ Each of these is preferably a hydrogen atom or a C1-6 alkyl group, and more preferably a hydrogen atom.

[0081] R in equation (Z-I) ４ Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group.

[0082] R in equation (Z-I) ５ Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group.

[0083] R ４ and R ５ In this context, "substituted or unsubstituted C1-6 alkyl groups", "substituted or unsubstituted C2-6 alkenyl groups", "substituted or unsubstituted C2-6 alkynyl groups", "substituted or unsubstituted C3-6 cycloalkyl groups", "substituted or unsubstituted phenyl groups", "substituted or unsubstituted naphthyl groups", "substituted or unsubstituted 5-6 membered heterocyclyl groups", and "halogeno groups" are as follows: １ , R ６ , R ７ and R ８ The same examples given in the previous section can be cited.

[0084] R on the same carbon atom ４ and R ５ These may combine to form a divalent organic group. Examples of divalent organic groups include C2-5 alkylene groups such as dimethylene, trimethylene, and tetramethylene groups.

[0085] Among these, R in equation (Z-1) ４ and R ５ Each of these preferably independently represents a hydrogen atom or a halogen group, and more preferably a hydrogen atom.

[0086] n is the number of repetitions of the structural unit within the brackets [ ], and represents an integer from 0 to 3, preferably an integer from 1 to 3. n is preferably 1 or 2, and more preferably 1. Alternatively, n may be 0.

[0087] The pyrazole compound of this embodiment is preferably a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt thereof. Each symbol in formula (I) has the same meaning as those in formula (Z-I).

[0088]

[0089] The pyrazole compound of this embodiment may also preferably be the compound represented by formula (Ia) (hereinafter sometimes referred to as compound (Ia)) or a salt thereof. Each symbol in formula (Ia) has the same meaning as those in formula (Z-I).

[0090]

[0091] The salt of compound (Z-I) is not particularly limited as long as it is an agrohorticulturally acceptable salt. Examples of salts of compound (Z-I) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; ammonia; and salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine.

[0092] The method for producing compound (Z-I) or a salt of compound (Z-I) is not particularly limited. For example, compound (Z-I) or a salt of compound (Z-I) can be obtained by known production methods described in the examples, etc. Alternatively, a salt of compound (Z-I) can be obtained from compound (Z-I) by known methods.

[0093] Manufacturing Intermediates: The compound represented by the formula (im-3) shown below, or a salt thereof, can serve as a manufacturing intermediate for compound (Z-I).

[0094]

[0095] In formula (im-3), R １ , R ２ and Q １ This is the same as defined in the compound of formula (Z-I). U represents a halogeno group, a hydroxyl group, or a C1-6 alkoxy group, preferably a hydroxyl group or a C1-6 alkoxy group.

[0096] The compound represented by the formula (im-3A) shown below, or a salt thereof, is preferred as a manufacturing intermediate for compound (Z-I).

[0097]

[0098] In formula (im-3A), R １ , and R ２ This is the same as defined in the compound of formula (Z-I). U represents a halogeno group, a hydroxyl group, or a C1-6 alkoxy group, preferably a hydroxyl group or a C1-6 alkoxy group. Q １ａ This represents a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted thiazolyl group, preferably a substituted or unsubstituted pyridyl group. Q １ａ However, when it is a substituted thiazolyl group, a C1-6 haloalkyl group is preferred as the substituent on the "thiazolyl group". Q １ａ However, when it is a substituted pyridyl group, halogeno groups, C1-6 alkyl groups, C1-6 haloalkyl groups, and C1-6 alkoxy groups are more preferred as substituents on the "pyridyl group".

[0099] [Manufacturing Method 1] Among the compounds of formula (im-3), the compound in which U is a C1-6 alkoxy group (referred to as the compound of formula (im-3a)) can be manufactured by a method including the reaction of the compound of formula (im-2) with the compound of formula (im-4), as shown in Scheme 1. The compound of formula (im-2) can also be manufactured by a method including the reaction and oxidation of the compound of formula (im-1) with a boron compound. Here, in each formula in Scheme 1, R １ , R ２ and Q １ This is the same as the definition for the compound of formula (Z-I). ａ X represents a C1-6 alkoxy group. X represents a halogeno group. ａ This indicates a halogen group.

[0100]

[0101] The compound of formula (im-3a) can be produced by reacting the compound of formula (im-2) with the compound of formula (im-4) by a well-known method. The reaction may be carried out in the presence of an acid scavenger. Examples of acid scavengers include general inorganic bases and organic bases. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred.

[0102] Among the compounds of formula (im-3), those in which U is a hydroxyl group (referred to as compounds of formula (im-3b)) can be produced by hydrolyzing the compound of formula (im-3a) under acidic or basic conditions. For example, this can be done by using trifluoroacetic acid to create acidic conditions, or by using lithium hydroxide in a mixed solvent system of an alcohol such as methanol, tetrahydrofuran (THF), and water to create basic conditions. Of these, the method under basic conditions is preferred. Among the compounds of formula (im-3), those in which U is a halogeno group (referred to as compounds of formula (im-3c)) can be produced by reacting the compound of formula (im-3b) with a halogenating reagent.

[0103] The compound of formula (im-4) may be commercially available or may be manufactured by a well-known method.

[0104] The compound of formula (im-2) may be commercially available or manufactured by well-known methods. Alternatively, the compound of formula (im-2) can be produced by reacting the compound of formula (im-1) with a boron compound in the presence of a palladium catalyst to convert it to an organoboron compound, and then oxidizing it. The method of conversion to an organoboron compound is the so-called Miyaura-Ishiyama borylation reaction. Examples of palladium catalysts include, but are not limited to, tetrakis(triphenylphosphine)palladium(O), bis(dibenzylideneacetone)palladium(O), tris(dibenzylideneacetone)dipalladium(O), bis(triphenylphosphine)palladium(II) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and [1,1'-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II). Examples of boron compounds include, but are not limited to, pinacol diborane, pinacol borane, and diboronic acid. The obtained organoboron compound can be oxidized with hydrogen peroxide under basic conditions to produce a compound of formula (im-2) in which the carbon-boron bond is replaced with a carbon-oxygen bond. The compound of formula (im-1) may be commercially available or produced by well-known methods.

[0105] A fungicide for agricultural and horticultural use according to one embodiment of the present invention contains at least one selected from the group consisting of compound (Z-I) and salts of compound (Z-I) as an active ingredient (hereinafter sometimes referred to as active ingredient (Z-I)). The amount of active ingredient (Z-I) contained in the fungicide for agricultural and horticultural use of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

[0106] The fungicide for agricultural and horticultural use of this embodiment can be used to control plant diseases caused by a wide range of filamentous fungi, such as those belonging to the algae (Oomycetes), ascomycetes, deuteromycetes, basidiomycetes, and zygomycetes.

[0107] Examples of plant diseases (pathogens) that are subject to control are shown below. Sugar beet: Brown spot (Cercospora beticola), black root rot (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf blight (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), leaf spot (Ramularia beticola), damping-off (Aphanomyces cochlioides, Pythium ultimum), etc. Peanut: Brown spot (Mycosphaerella arachidis), stain spot (Ascochyta sp.), rust (Puccinia arachidis), damping-off (Pythium debaryanum), rust spot (Alternaria alternata), white mold (Sclerotium rolfs II), black rot (Mycosphaerella berkeleyi), black root rot (Calonectria) Cucumbers: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine wilt (Fusarium oxysporum), sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassIIcola), seedling blight (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial leaf spot (Pseudomonas syringae pv. Lachrymans), etc. Tomatoes: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), hemi-wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (OidiumEggplant: Neolycopersici, ring spot disease (Alternaria solani), sooty mold (Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), sclerotinia rot (Sclerotinia sclerotiorum), etc. Eggplant: Gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), sooty mold (Mycovellosiella nattrass II), sclerotinia rot (Sclerotinia sclerotiorum), Verticillium dahliae, brown spot disease (Phomopsis vexans), etc. Chili pepper: Late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), anthracnose (Colletotrichum aenigma, Colletotrichum Strawberries: Capsici (Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberries: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopus stolonifer), fusarium oxysporum, wilt (Verticillium dahliae), sclerotinia sclerotiorum, etc. Onions: Gray rot (Botrytis all II), gray mold (Botrytis cinerea), white spot leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor), white blight (Phytophthora porri), Ciborinia allII, Botrytis squamosa, Fusariumoxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotium (Sclerotium cepivorum), rust (Puccinia allII), white silk rot (Sclerotium rolfsII), etc. Allium: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora) cabbage: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. Lettuce: maculicola, P. s. pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinia sclerotiorum, sooty mold (Alternaria brassicola), gray mold (Botrytis cinerea), root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), white rust (Albugo macrospora), etc. Lettuce: rot (Pseudomonas cichor II, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, big vein disease (Mirafiori lettuce big-vein ophiovirus), root rot (Fusarium oxysporum), bottom blight (Rhizoctonia solani), powdery mildew (Golovinomyces)Green beans (e.g., oront II): Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), horn spot disease (Phaeoisariopsis griseola), etc. Peas: Mycosphaerella blight, gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, powdery mildew (Erysiphe pisi), etc.

[0108] Apples: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), Monilinia mali, black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), cedar-apple rust (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty mold (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), burn (Erwinia amylovora), silver leaf (Chondrostereum) Plum: Black spot (Cladosporium carpophilum), gray mold (Botrytis cinerea), gray mold (Monilinia mumecola), sooty mold (Peltaster sp.), fruit rot (Taphrina pruni), brown hole (Phloeosporella padi), etc. Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), horn spot leaf spot (Cercospora kaki), round leaf spot leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty spot (Zygophiala jamaicensis), etc. Peach: Gray mold (Monilinia fructicola, Monilia fructigena), black spot disease (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), perforation bacterial disease (Xanthomonas campestris pv.)pruni), leaf curl disease (Taphrina deformans), charcoal disease (Colletotrichum gloeosporioides), brown hole disease (Phloeosporella padi), kawara take disease (Coriolus versicolor) nado armond: gray star disease (Monilinia laxa), spot disease (Stigmina carpophila), black star disease (Cladosporium carpophilum), leaf disease (Polystigma rubrum), spotted leaf disease (Alternaria alternata), anthracnose (Colletotrichum gloeospoides) nado ooto: gray star disease (Monilinia fructicola), charcoal disease (Colletotrichum acutatum), black spot disease (Alternaria sp.).Grapes: Gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late blight (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwell II), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white snow disease (pathogen unidentified), crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: Black spot (Venturia nashicola), cedar-apple rust (Gymnosporangium) asiaticum, black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukush II), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: ring spot (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red blight (Pseudomonas syringae), blight (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcett II), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe) Citri), canker (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.Kiwifruit: Bacterial blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc.; Bacterial canker (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytiscinerea), soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty mold (Pseudocercospora actinidiae), etc.; Olive: Anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), Peacock spot (Spilocaea oleaginea), etc.; Chestnut: Anthracnose (Colletotrichum gloeosporioides), etc.

[0109] Wheat: powdery mildew (Blumeria graminis f.sp. tritici), scab (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), brown rust (Puccinia recondita), yellow rust (Puccinia striiformis), brown snow blight (Pythium iwayamai), red snow blight (Monographella nivalis), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Leptosphaeria nodorum), pink snow mold (Typhula incarnata), large snow mold (Myriosclerotinia borealis), take-all (Gaeumannomyces graminis), ergot (Claviceps purpurea), common bunt (Tilletia caries), loose smut (Ustilago nuda), blast (Pyricularia grisea), damping-off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: leaf stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), rhynchosporium (Rhynchosporium secalis), loose smut (Ustilago tritici, U. nuda), damping-off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Rice: blast (Pyricularia oryzae), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), sesame leaf blight (CochliobolusTobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), late blight (Phytophthora nicotianae), etc. Tulips: gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf blight (Rhizoctonia rhizome), brown stripe disease (Acidovorax avenae), bacterial blight (Burkholderia glumae), streaky leaf blight (Cercospora oryzae), blast disease (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black-bellied rice (Alternaria padwick II), red-colored rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), late blight (Phytophthora nicotianae), etc. Tulips: gray mold (Botrytis cinerea), brown spot disease (Botrytis tulipae), leaf blight (Rhizoctonia rhizome) Roses: Black spot (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Chrysanthemums: Gray mold (Botrytis cinerea), white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium wilt (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), wilt (Rhizoctonia solani), Fusarium wilt (Fusarium solani), etc. Gerberas: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera Lilies such as xanth II: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (BotrytisSunflowers: Downy mildew (Plasmopara halsted II), Sclerotinia sclerotiorum, Gray mold (Botrytis cinerea), etc. Bentgrass: Snow mold (Sclerotinia borealis), Large patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot (Sclerotinia homoeocarpa), Blast (Pyricularia sp.), Red blight (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc. Orchardgrass: Powdery mildew (Erysiphe graminis), etc. Soybeans: Purple spot (Cercospora kikuch II), Downy mildew (Peronospora manshurica), Stem blight (Phytophthora sojae), Rust (Phakopsora Potatoes: Late blight (Phytophthora infestans), summer blight (Alternaria solani), black spot (Thanatephorus cucumeris), Verticillium albo-atrum, V. dahliae, V. nigrescens), black foot (Pectobacterium) (Atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia (Sclerotinia)Japanese yam (Cylindrosporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potato (Helicobasidium mompa), vine rot (Fusarium oxysporum), etc. Taro (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger (Pythium ultimum, Pythium myriotylum), white spot (Phyllosticta zingiberis), etc. Banana (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango (Colletotrichum aenigma), canker (Xanthomonas Rapeseed: Campestris, stem rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc. Rapeseed: Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), downy mildew (Peronospora parasitica), etc. Coffee: Rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia) Corn (including Melanocephala): Gloeocercospora sorghi, Puccinia sorghi, Puccinia polysora, UstilagoMaydis, Cochliobolus heterostrophus, Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Seedling blight (Pythium sp.), Rust (Phakopsora gossyp II), White mold (Mycosphaerella areola), Anthracnose (Glomerella gossyp II), etc. Hops: Downy mildew (Pseudoperonospora humuli), Powdery mildew (Oidium sp., Podosphaera macularis), Gray mold (Botrytis cinerea), etc.

[0110] The fungicide for agricultural and horticultural use of this embodiment is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee, and cocoa, pasture grasses, turfgrasses, and cotton.

[0111] The fungicide for agricultural and horticultural use of this embodiment can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, rhizomes, seedlings, and cuttings. Furthermore, it can be used to target improved varieties, cultivars, and even mutants, hybrids, and genetically modified organisms (GMOs) of these plants.

[0112] The fungicide for agricultural and horticultural use of this embodiment can be used for seed treatment, foliar application, soil application, water surface application, etc., to control various diseases that occur in agricultural and horticultural crops, including flowers, turf, and pasture grass. Among these, the fungicide for agricultural and horticultural use of this embodiment is preferably for seed treatment.

[0113] The fungicide for agricultural and horticultural use of this embodiment may contain other components besides the active ingredient (Z-I). Examples of other components include known carriers used for formulation. Other components may include conventionally known fungicides, insecticides / acaricides, nematicides, soil pesticides, plant growth regulators, synergists, fertilizers, soil conditioners, animal feed, etc. (hereinafter sometimes referred to as active ingredient (II)). The fungicide for agricultural and horticultural use of this embodiment may exhibit a synergistic effect by containing both active ingredient (Z-I) and active ingredient (II).

[0114] Specific examples of fungicides as active ingredient (II) that can be mixed with or used in combination with the agricultural and horticultural fungicide of this embodiment are shown below.

[0115] (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: Benalaxil, Benalaxil-M, Flalaxil, Metalaxil, Metalaxil-M, Oxadixil, Clodilacon, Oflace; (b) Adenosine deaminase inhibitors: Bupirimate, Dimethyrimol, Ethyrimol; (c) DNA / RNA synthesis inhibitors: Himexazole, Octylinone; (d) DNA topoisomerase II inhibitors: Oxolinic acid; (e) DHODH inhibitors: Ipuflufenoquine, Quinofumerine

[0116] (2) Mitogenic inhibitors and cell division inhibitors: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, etaboxam; (b) cell division inhibitor: pencyclon; (c) spectrin-like protein delocalization inhibitors: fluopicolide, fluopimomide; (d) actin / myosin / fimbrin function: phenamacryl, metraphenone, pyriophenone; (e) tubulin dynamics modulator: pyridaclomethyl;

[0117] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad, phenazaquin; (b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenflam, flumecyclox, carboxyne, oxycarboxyne, tifluzamide, benzovindiflupir, bixafen, fluxapyroxad, flametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pidflumetofen, isoflucipram, pyraziflumid, impilfluxam; (c) Complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, chemoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidon, pyribencarb, methyltetraprole, mandestrobin; (d) Complex III-ubiquinol reductase Qi inhibitors: cyazofamide, amisulbrom, fenpicoxamide, florylpicoxamide; (e) Uncoupling agents for oxidative phosphorylation: binapacril, meptyldinocap, dinocap, fluazinam; (f) Oxidative phosphorylation inhibitors (ATP synthase inhibitors): fentin acetate, fentin chloride, fentin hydroxylated; (g) ATP production inhibitors: silthiofams; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctrazine;

[0118] (4) Amino acid and protein synthesis inhibitors: (a) Methionine biosynthesis inhibitors: andprim, cyprodinil, mepanipyrim, pyrimethanil; (b) Protein synthesis inhibitors: blastosidine-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline; (c) Leucyl-tRNA synthetase inhibitors: tababolol;

[0119] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxyfen, proquinazide; (b) MAP histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, clozolinate, dimethacron, iprodione, procymidone, vinclozoline;

[0120] (6) Lipid and cell membrane synthesis inhibitors: (a) Phospholipid biosynthesis and methyltransferase inhibitors: edifenphos, ipropenphos, pyrazophos, isoprothiolane; (b) Lipid peroxidants: biphenyl, chloreneb, dichlorane, quintozen, technazen, tolclophosmethyl, etridiazole; (c) Cell membrane acting agents: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb focetilate, prothiocarb; (d) Cell membrane disrupting agents: extract of tea tree; (e) Agents that specifically bind to ergosterol: natamycin;

[0121] (7) Inhibitors of cell membrane sterol biosynthesis: (a) Inhibitors of C14 demethylation in sterol biosynthesis: Triforine, pyrifenox, pyrisoxazole, phenalimol, flurprimidol, nualimol, imazalil, imazalil sulfate, oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, vitertanol, bromconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole - M, epoxyconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, mycrobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: Algimorph, Dodemorph, Dodemorph acetate, Fenpropimorph, Tridemorph, Fenpropidine, Piperalin, Spiroxamine; (c) Inhibitors of 3-keto reductase in C4 demethylation of the sterol biosynthesis system: Fenhexamide, Fenpyrazamine; (d) Inhibitors of squalene epoxidase in the sterol biosynthesis system: Pyributicarb, Naphthifine, Terbinafine;

[0122] (8) Cell wall synthesis inhibitors: (a) Chitin synthase inhibitors: Polyoxin, Polyoxorim; (b) Cellulose synthase inhibitors: Dimethomorph, Flumorph, Pyrimorph, Benciavaricarb, Benciavaricarb isopropyl, Iprovalicarb, Valifenarate, Mandipropamide;

[0123] (9) Melanin biosynthesis inhibitors: (a) Melanin biosynthesis reductase inhibitors: Phthalide, pyroquilon, tricyclazole; (b) Melanin biosynthesis dehydrase inhibitors: Carpropamide, diclocimet, phenoxanil; (c) Melanin biosynthesis polyketide synthesis inhibitors: Tolprocarb;

[0124] (10) Resistance-inducing agents for host plants: (a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl, probenazole, thiadinyl, isothianil, diclobentiazox; (b) Others: ibuphentrifluconazole, laminarin, knotweed extract; fosetylaluminum, fosetylcalcium, fosetylsodium, phosphoric acid, phosphate, phosphorous acid, phosphate;

[0125] (11) Agents with unknown mode of action: cymoxanil, tecrophthalam, triazoxide, furusulfamide, diclomedin, cyflufenamide, dozin, dozin free base, fluthianil, ferimzon, tebufloxin, picarbtrazox, validamycin;

[0126] (12) Agents with multiple sites of action: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ambam, farbam, mancozeb, maneb, mancapper, methylam, methylam zinc, polycarbamate, propineb, thyram, zineb, zillam; captan, captafoll, forpet, chlorothalonil, diclofluanide, tolfluanide, guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine trialbesylate, anilazine, dithianone, quinomethionate, fluorimide, metasulfocarb;

[0127] (13) Other agents: DBEDC, Fluorofolpet, Bis(8-Quinolinolate)copper(II), Propamidine, Chloropicrin, Cyproflam, Agrobacterium, Bethoxazine, Diphenylamine, Methylisothiocyanate (MITC), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumetobel, Irmamycin, Nitrotar Isopropyl, Oxamocarb, Pyrrolenitrin, Torniphanide, Zarilamid, Algophase, Amicalthiazole, Oxathiapiproline, Fluoxapiproline, Benzazole, Triclamide, Uniconazole, Oxyphenthiin, Pirapropoin, Fluindapyr, Aminopyrifene, Dipimethitrone, Fluphenoxadiazam, Flumethylsulforim, Feneptamidocine;

[0128] (14) Biologics with multiple mechanisms of action: Trichoderma atroviride I-1237 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride LU132 strain, Trichoderma atroviride SC1 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride 77B strain; Trichoderma aspererum T34 strain, Trichoderma aspererum kd strain; Trichoderma halzianum T-22 strain; Trichoderma Derma virens G-41 strain; Chronostachys rosea J1146 strain, Chronostachys rosea CR-7 strain; Coniothirium minitans CON / M / 91-08 strain; Hanseniaspora ubaraum BC18Y strain; Talaromyces flavus SAY-Y-94-01 strain; Saccharomyces cerevisiae LAS02 strain, Saccharomyces cerevisiae DDSF623 strain; Bacillus amyloric Bacillus amyloriquefaciens QST713 strain, Bacillus amyloriquefaciens FZB24 strain, Bacillus amyloriquefaciens MBI600 strain, Bacillus amyloriquefaciens D747 strain, Bacillus amyloriquefaciens F727 strain, Bacillus amyloriquefaciens AT-332 strain; Bacillus subtilis AFS032321 strain, Bacillus subtilis Y1336 strain, Bacillus subtilis HAI-0404 strain, Bacillus subtilis RTI477 strain; Bacillus berezensis RTI301 strain; PHC25279; Gluconobacter serinas BC18B strain; Pseudomonas chlororaffis ASF009 strain; Pseudomonas rhodesia HAI-0804 strain; Streptomyces griseobilides K61 strain; Streptomyces riddix WYEC108 strain.

[0129] Specific examples of insecticides, acaricides, nematicides, soil pesticides, and anthelmintics that can be mixed with or used in combination with the fungicide for agricultural and horticultural use of this embodiment are shown below.

[0130] (1) Acetylcholinesterase (AChE) inhibitors (a) Carbamate acetylcholinesterase (AChE) inhibitors: Alanicarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimicarb, Propoxul, Thiodicarb, Thiofanox, Triazamate, Trimetacarb, XMC, Xylylcarb; Phenothiocarb, MIPC, MPMC, MTMC, Aldoxicarb, Alixicarb, Aminocarb, Bufencarb, Chloetocarb, Metam sodium, Promecarb;(b) Organophosphorus acetylcholinesterase (AChE) inhibitors: Acephate, Azamethiphos, Adinphos-ethyl, Adinphos-methyl, Kazsaphos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos, Diclotophos, Dimethoate, Dimethylvinphos, Disulfon, EPN, Ethion, Etoprophos, Fanflu, Phenamiphos, Fenitrothion, Fenthion, Fostiazate, Heptenophos, Imisiaphos, Isofenphos, Isocarbophos, Isopropyl-O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Metamidophos, Methidathion, Mevinphos, Monoclotophos, Nared, Omethoate, Oxydimetonmethyl, Parathion, Para Thione methyl, fenthoate, phorate, fosalon, fosmet, phosphamidone, foxim, pyrimiphos methyl, profenofos, propetamfos, prothiofos, pyraclofos, pyridaphenthion, quinalfos, sulfotep, tebupyrimfos, temefos, terbufos, tetrachlorvinfos, thiometon, triazofos, trichlorfon, bamidothion, bromophos ethyl, BRP, carbophenothion, cyanophenfos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, honofos, formothion, fosmetylane, isazofos, iodophenfos, methacryfos, pyrimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos;

[0131] (2) GABAergic chloride ion channel blockers: Chlordane, endosulfan, ethiprole, fipronil; acetoprole, pyrafluprole, pyriprole, campechlor, heptachlor, dienochlor, flufiprol;

[0132] (3) Sodium channel modulators (a) Pyrethroid sodium channel modulators: Acrinatrin, Allethrin, d-cistrans-Allethrin, d-trans-Allethrin, Bifenthrin, Bioallethrin, Bioallethrin-S-cyclopentenyl isomer, Biorethmetrin, Cycloprotrin, Cyfluthrin, β-Cyfluthrin, Cyhalothrin, λ-Cyhalothrin, γ-Cyhalothrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, θ-Cypermethrin Lumethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, cadesrin, permethrin, phenothrin Phosphorus [(1R)-trans isomer], prallethrin, pyrethram, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioetanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metofluthrin, protrefenbut, pyrethmethrin, terarethrin, κ-bifenthrin, chloroprarethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioetanomethrin; (b) Sodium channel modulators (DDTs): DDT, methoxychlor;

[0133] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradiflon, dichloromesothiaz, fenmesoditiaz, triflumesopyrim, flupyrimin; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinetram, spinosad; (6) Glutamate-gated chloride ion (chloride ion) channel (GluCl) allosteric modulators: Abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;

[0134] (7) Juvenile hormone analogues: Hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen; diofenolan, epophenonane, triprene; (8) Other nonspecific (multisite) inhibitors: 1,3-dichloropropene, methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartaric acid, dazomet, metam, potassium metam, sodium metam; (9) Cranial organ TRPV channel modulators: Pymetrozine, pyrifluquinazon, afidopiropene; (10) Mite growth inhibitors: Clofentezine, diflovidazine, hexythiazox, etoxazole; (11) Microbial insect midgut endometrium disruptors: Proteins contained in Bacillus thuringiensis subspecies islaerensi, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies krustaki, Bacillus thuringiensis subspecies tenebryonis, Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus;

[0135] (12) Mitochondrial ATP synthase inhibitors: diafenthiurone, azocyclotin, cyhexatine, fenbutasin oxide, propargit, tetradiphon; (13) Oxidative phosphorylation uncoupling agents that disrupt the proton gradient: chlorfenapyr, DNOC, sulfuramide; binapacril, dinovton, dinocap; (14) Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt; nereistoxin; (15) Chitin biosynthesis inhibitors, type 0: bistriflurone, chlorfluazurone, diflubenzuron, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, nobiflumuron, teflubenzuron, triflumuron; buprofezin, fluazurone; (16) Chitin biosynthesis inhibitors, type 1: Buprofezin; (17) Molting inhibitors: Cyromazine; (18) Molting hormone (ecdysone) receptor agonists: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

[0136] (19) Octopamine receptor agonists: Amitraz; Demiditraz, Chlordimeform; (20) Mitochondrial electron transport chain complex III inhibitors: Hydramethylnon, Acequinosyl, Fluacrypyrim, Bifenazate; (21) Mitochondrial electron transport chain complex I inhibitors (METI): Phenazaquine, Fenpyroximate, Pyridaben, Pyrimidifene, Tebufenpyrad, Tolfenpyrad, Rotenone; (22) Voltage-gated sodium channel blockers: Indoxacarb, Metaflumizone; (23) Acetyl-CoA carboxylase inhibitors: Spidoxamato, Spirodiclofen, Spiromesifen, Spiropidione, Spirotetramato; (24) Mitochondrial electron transport chain complex IV inhibitors: Aluminum phosphide, Calcium phosphide, Zinc phosphide, Phosphine, Cyanide, Calcium cyanide, Sodium cyanide, Potassium cyanide; (25) Mitochondrial electron transport chain complex II inhibitors: cyenopyrafen, cyflumetofen, piflubumide;

[0137] (26) Rianodine receptor modulators: Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetraniliprole; tetrachlorantraniliprole; (27) Cranial organ modulators with unspecified target site: Flunicamide; (28) GABAergic chloride ion (chloride ion) channel allosteric modulators: Fluxamethamide, isocycloceram, brofuranilide; afoxolaner, fluralaner, rotineral, sarolaner; (29) Other insecticides and acaricides: Acinonapyr, flomethin, redoprona, zinnpropyridaz, oxazosulfyl, azadirachtin, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, dicofol, lime sulfur mixture, mancozeb, pyridaryl, sulfur; Cryolite, Bencrothiaz, Amidoflumet, DCIP, Phenisobromolate, Benzomate, Metaldehyde, Chlorbenzilate, Clothiazoben, Dicyclanil, Phenoxacrim, Fentriphanil, Flubenzimine, Fluphenazine, Gossiplua, Japonilua, Methoxadiazone, Petroleum (oil), Potassium Oleate, Tetrasul, Triaracene, Afidopiropene, Flufiprol, Fluensulfol Meperflusrin, tetramethylflusrin, tralopyril, dimeflusrin, methylneodecanamide, broflanilide, Steiner's nema capocapsae, Steiner's nema glacerai, Pastouria penetrans, Pechylomyces stenuipes, Pechylomyces phmosoroseus, Beauveria bassiana, Beauveria bronniati, Metallidium anisoplie, Verticillium lecani, fulhexaphon, cyclopyrazoflor;

[0138] (30) Anthelmintics: (a) Benzimidazoles: Fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambendazole; (b) Salicylanilides: Closantel, oxyclozanide, lafoxanide, niclosamide; (c) Substituted phenols: Nitroxynil, nitroscanate; (d) Pyrimidines: Pyrantel, morantel; (e) Imidazothiazoles: Lebamisol, tetramisol; (f) Tetrahydropyrimidines: Praziquantel, epsiplantel; (g) Other anthelmintics: Cyclodiene, Lianya, Chlorthrone, Metronidazole, Demiditraz, Piperazine, Diethylcarbamazine, Dichlorophene, Monepantel, Tribenzimidine, Amidantel, Thiacetalthamide, Melalsomine, Arsenamide.

[0139] Specific examples of plant growth regulators as active ingredient (II) that can be mixed with or used in combination with the fungicide for agricultural and horticultural use of this embodiment are shown below: Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothic acid Ole, 1-Naphthylacetamide, Ethiclozate, Cloxihonac, Hydrazide Maleate, 2,3,5-Triiodobenzoic Acid, Salicylic Acid, Methyl Salicylate, (-)-Jasmonic Acid, Methyl Jasmonate, (+)-Strigol, (+)-Deoxystrigol, (+)-Orobancol, (+)-Solgolactone, 4-Oxo-4-(2-Phenylethyl)aminobutyric Acid, Ethephon, Chlormecoat, Mepicote Chloride, Benzyladenine, 5-Aminolevulinic Acid, Daminozide.

[0140] Active ingredients (Z-I) and (II) may exhibit a synergistic effect when mixed or used in combination. The synergistic effect can be confirmed using Colby's formula. For example, it can be confirmed by the following method: Gray mold antimicrobial test (growth inhibition rate) Conidia of gray mold fungus (Botrytis cinerea) are added to yeast extract sucrose medium and dispersed. Then, active ingredients (Z-I) and (II) at predetermined concentrations dissolved in dimethyl sulfoxide are added and mixed. These are dispensed onto 96-well microplates and cultured in the dark at 20°C for 3 to 5 days. After culturing, the turbidity at a wavelength of 405 nm is measured with a microplate reader, and the growth inhibition rate (%) of gray mold fungus compared to the untreated case is determined. It is preferable to perform the test in two or more series. From the obtained results, the expected value is calculated using Colby's formula below. Colby's formula: E = M + N - MN / 100 In the formula, E is the expected value of the growth inhibition rate (%), M is the growth inhibition rate (%) when the active ingredient (Z-I) is used alone (%), and N is the growth inhibition rate (%) when the active ingredient (II) is used alone (%). When the measured growth inhibition rate (%) of the composition of active ingredients (Z-I) and (II) is greater than the expected value E, the composition of active ingredients (Z-I) and (II) will produce a synergistic effect.

[0141] {Formulation} The fungicide for agricultural and horticultural use of the present invention is not particularly limited in terms of dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, water-soluble powders, suspensions, granular wettable powders, and tablets can be used. The method of preparing the formulation is not particularly limited, and known preparation methods can be used depending on the dosage form.

[0142] The following are some examples of formulations. The formulations shown below are merely illustrative and can be modified insofar as they do not contradict the spirit of the present invention, and the present invention is not limited in any way by the following examples of formulations. Unless otherwise specified, "parts" means "parts by mass".

[0143] (Formulation Example 1: Wettable Powder) 40 parts of the pyrazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed, and then finely ground to obtain a wettable powder containing 40% by mass of the active ingredient.

[0144] (Formulation Example 2: Emulsion) 30 parts of the pyrazole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% by mass of the active ingredient.

[0145] (Formulation Example 3: Granules) Five parts of the pyrazole compound of the present invention, forty parts of talc, thirty-eight parts of clay, ten parts of bentonite, and seven parts of alkyl sodium sulfate are uniformly mixed, then finely ground, and then granulated to a particle diameter of 0.5 to 1.0 mm to obtain granules containing 5% by mass of the active ingredient.

[0146] (Formulation Example 4: Granules) Five parts of the pyrazole compound of the present invention, seventy-three parts of clay, twenty-tenths of bentonite, one part of sodium dioctyl sulfosuccinate, and one part of potassium phosphate are uniformly mixed and pulverized, then water is added and kneaded. After that, the mixture is granulated and dried to obtain granules containing 5% by mass of the active ingredient.

[0147] (Formulation Example 5: Suspension) 10 parts of the pyrazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-ground until the particle size is 3 microns or less to obtain a suspension containing 10% by mass of the active ingredient.

[0148] (Formulation Example 6: Granular Wettable Powder) 40 parts of the pyrazole compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzene sulfonate, 8 parts of sodium lignin sulfonate, and 5 parts of formaldehyde condensate of sodium alkylbenzene sulfonate are uniformly mixed and finely ground. Then, an appropriate amount of water is added and kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a granular wettable powder containing 40% by mass of the active ingredient.

[0149] Next, the present invention will be explained in more detail by showing examples of compound preparation. However, the present invention is not limited in any way by the following examples.

[0150] [Example 1] Compound 1 was prepared by the following steps: (Step 1) Conversion to methyl 1-(tert-butyl)-4-iodo-1H-pyrazole-5-carboxylate

[0151]

[0152] 13.7 g of methyl 1-(tert-butyl)-1H-pyrazole-5-carboxylate was dissolved in acetic acid (150 mL). N-iodosucciimide (18.6 g) was added, and the mixture was stirred at 50°C for 6 hours. Then, another 0.846 g of N-iodosucciimide was added, and the mixture was stirred at 50°C for another 6 hours. The mixture was quenched with dilute hydrochloric acid, extracted with ethyl acetate, and the extract layer was washed with saline solution. The mixture was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the compound was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 20 g of the target compound (yield 85%).

[0153] (Step 2) Conversion to 1-(tert-butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate

[0154]

[0155] 17.3 g of methyl 1-(tert-butyl)-4-iodo-1H-pyrazole-5-carboxylate was dissolved in dimethyl sulfoxide (187 mL). To this, 28.5 g of bis(pinacolato)diborone, 2.29 g of the dichloromethane complex of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and 16.5 g of potassium acetate were added, and the mixture was stirred at 100°C for 1 hour under a nitrogen atmosphere. The reaction mixture was filtered through Celite and extracted with ethyl acetate. Subsequently, it was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the compound was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 17.3 g of the target compound (100% yield).

[0156] (Step 3) Conversion to 1-(tert-butyl)-4-hydroxy-1H-pyrazole-5-carboxylate

[0157]

[0158] 1-(tert-butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate methyl (23.5 g) was dissolved in ethanol (152 mL), then sodium carbonate (16.1 g) was added and the mixture was stirred under ice cooling. 30% hydrogen peroxide (22.2 g) was added and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with aqueous sodium sulfite solution and then acidified with dilute hydrochloric acid. After removing the ethanol under reduced pressure, the aqueous bath was extracted with ethyl acetate, and the extracted phase was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the compound was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 7.2 g of the target compound (yield 48%).

[0159] (Step 4) Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-pyrazole-5-carboxylate (production intermediate a-1)

[0160]

[0161] 0.250 g of methyl 1-(tert-butyl)-4-hydroxy-1H-pyrazole-5-carboxylate was dissolved in 6.3 mL of N,N-dimethylformamide. 0.249 g of 6-chloro-2-fluoropyridine and 0.261 g of potassium carbonate were added, and the mixture was stirred overnight at 90°C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extracted phase was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the compound was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.38 g of the target compound (production intermediate a-1) (yield 97%).

[0162] (Step 5) Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-pyrazole-5-carboxylic acid (manufacturing intermediate a-2)

[0163]

[0164] 0.75 g of 1-(tert-butyl)-4-((6-chloropyridine-2-yl)oxy)-1H-pyrazole-5-carboxylate methyl was dissolved in methanol (6.1 mL). 2.5 mL of 2 M aqueous sodium hydroxide solution was added, and the mixture was stirred overnight at 40°C. The reaction mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.29 g of the target compound (production intermediate a-2) (yield 80%).

[0165] (Step 6) Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(2,4-dimethylphenethyl)-1H-pyrazole-5-carboxamide (Compound 1)

[0166]

[0167] 1-(tert-butyl)-4-((6-chloropyridine-2-yl)oxy)-1H-pyrazole-5-carboxylic acid (0.050 g) was dissolved in dichloromethane (1.7 mL). To this, 2-(2,4-dimethylphenyl)ethylamine (0.050 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (0.13 g) and triethylamine (0.051 g) were added and the mixture was stirred overnight at room temperature. The reaction mixture was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.068 g of the target compound (compound 1) (yield 94%).

[0168] [Example 2] Compound 6 (1-(tert-butyl)-N-(4-methoxy-2-methylphenethyl)-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxamide) was prepared by the following steps.

[0169] (Step 1) Conversion to 1-(tert-butyl)-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylate

[0170]

[0171] 0.500 g of methyl 1-(tert-butyl)-4-hydroxy-1H-pyrazole-5-carboxylate was dissolved in 25.2 mL of N,N-dimethylformamide. 1.42 g of 2-chloro-4-(trifluoromethyl)thiazole and 0.697 g of potassium carbonate were added, and the mixture was stirred overnight at 60°C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extracted phase was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the compound was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.71 g of the target compound (yield 81%).

[0172] (Step 2) Conversion to 1-(tert-butyl)-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxylic acid

[0173]

[0174] 0.71 g of 1-(tert-butyl)-4-((4-(trifluoromethyl)thiazole-2-yl)oxy)-1H-pyrazole-5-carboxylate methyl was dissolved in methanol (10 mL). 4.1 mL of 2 M aqueous sodium hydroxide solution was added, and the mixture was stirred overnight at 40°C. The reaction mixture was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.35 g of the target compound (yield 51%).

[0175] (Step 3) Conversion to 1-(tert-butyl)-N-(4-methoxy-2-methylphenethyl)-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxamide

[0176]

[0177] 1-(tert-butyl)-4-((4-(trifluoromethyl)thiazole-2-yl)oxy)-1H-pyrazole-5-carboxylic acid (0.050 g) was dissolved in tetrahydrofuran (1.5 mL). To this, 2-(4-methoxy-2-methylphenyl)ethane-1-amine hydrochloride (0.045 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (0.11 g) and triethylamine (0.045 g) were added and the mixture was stirred overnight at room temperature. The reaction mixture was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.053 g of the target product (yield 74%).

[0178] [Example 3] 1-(tert-butyl)-N-((4-methoxy-2-methylbenzyl)oxy)-4-((4-(trifluoromethyl)thiazol-2-yl)oxy)-1H-pyrazole-5-carboxamide was prepared by the following steps. Synthesis of (Compound No. A-8)

[0179]

[0180] 1-(tert-butyl)-4-((4-(trifluoromethyl)thiazole-2-yl)oxy)-1H-pyrazole-5-carboxylic acid (0.050 g) was dissolved in tetrahydrofuran (2 mL). To this, O-(4-methoxy-2-methylbenzyl)hydroxylamine hydrochloride (0.046 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (0.11 g) and triethylamine (0.045 g) were added and the mixture was stirred overnight at room temperature. The reaction mixture was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.011 g of the target product (yield 15%).

[0181] [Example 4] 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide was prepared by the following steps. Synthesis of Compound No. 36 (Step 1) Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(4-cyanophenethyl)-1H-pyrazole-5-carboxamide

[0182]

[0183] 1-(tert-butyl)-4-((6-chloropyridine-2-yl)oxy)-1H-pyrazole-5-carboxylic acid (0.5 g) was dissolved in tetrahydrofuran (16.9 mL). To this, 4-(2-aminoethyl)-3-methylbenzonitrile hydrochloride (0.624 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (1.29 g) and triethylamine (0.684 g) were added, and the mixture was stirred overnight at 40°C. After the reaction was complete, the reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.70 g of the target compound (yield 97%).

[0184] (Step 2) Conversion to (Z)-1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(4-(N'-hydroxycarbamimidoyl)phenethyl)-1H-pyrazole-5-carboxamide

[0185]

[0186] 1-(tert-butyl)-4-((6-chloropyridine-2-yl)oxy)-N-(4-cyanophenethyl)-1H-pyrazole-5-carboxamide (0.70 g) was dissolved in ethanol (16 mL). Hydroxylamine aqueous solution (0.33 g) was added, and the mixture was stirred at 80°C for 1 hour. After the reaction was complete, the reaction mixture was removed by distillation under reduced pressure to obtain 0.75 g of the target compound (yield 99%).

[0187] (Step 3) Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide

[0188]

[0189] (Z)-1-(tert-butyl)-4-((6-chloropyridine-2-yl)oxy)-N-(4-(N'-hydroxycarbamidoyl)phenethyl)-1H-pyrazole-5-carboxamide (0.080 g) was dissolved in N,N-dimethylformamide (1.8 mL). Cyclopropanecarboxylic acid anhydride (0.027 g) and potassium carbonate (0.036 g) were added while cooling in an ice bath, and the mixture was stirred at 40°C for 15 minutes, then stirred at 80°C for 2 hours. After the reaction was complete, water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was then washed with brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to obtain 0.009 g of the target product (yield 10%).

[0190] The compounds shown in Tables 5 and 6 were prepared using the same process as described in the above manufacturing example. The melting point or appearance (viscous oil or amorphos) is noted in the properties column. For compounds with a viscous oil or amorphos appearance, the LCMS retention time is noted.

[0191] The LC-MS (SQD2) retention time was determined by the following method. A CORTECS UPLC C18 column (Waters, 2.1 × 50 mm, 1.6 μm) was attached to a system consisting of an ultrafast high-resolution liquid chromatograph (ACQUITY UPLC H-Class: Waters), an HPLC / UHPLC detector (ACQUITY UPLC photodiode array (PDA) eλ detector (Waters)), and a single quadrupole MS detector (LC / MS) (SQ Detector 2 detector (positive and negative ion electrospray mode and atmospheric pressure chemical ionization mode) (Waters)). The measurement was performed at a temperature of 40°C, a flow rate of 0.6 mL / min, and a 2 μL injection. Water containing 0.1% by mass of formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). The concentration of mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then the concentration of mobile phase (B) was increased at a constant rate from 30% by mass to 95% by mass over 1.35 minutes and maintained at 95% by mass for 0.5 minutes, then the concentration of mobile phase (B) was immediately reduced to 30% by mass, and finally the concentration of mobile phase (B) was maintained at 30% by mass for 0.50 minutes.

[0192] The LC-MS (QDa) retention time was determined by the following method. A CORTECS UPLC C18 column (Waters, 2.1 × 50 mm, 1.6 μm) was attached to a system consisting of an ultrafast high-resolution liquid chromatograph (ACQUITY UPLC H-Class: Waters), an HPLC / UHPLC detector (ACQUITY UPLC photodiode array (PDA) eλ detector (Waters)), and a single quadrupole MS detector (LC / MS) (ACQUITY QDa detector (positive and negative ion electrospray mode) (Waters)). The retention time was measured at a temperature of 40°C, a flow rate of 0.6 mL / min, and a 2 μL injection. Water containing 0.1% by mass of formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). The concentration of mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then increased at a constant rate from 30% by mass to 95% by mass over 1.35 minutes, maintained at 95% by mass for 0.5 minutes, then immediately decreased to 30% by mass, and finally maintained at 30% by mass for 0.50 minutes.

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] Table 7 below shows compounds that can serve as manufacturing intermediates. The structural formulas of the manufacturing intermediates are shown along with their LC-MS retention times.

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220] The effects of the present invention are illustrated by the following sterilization efficacy tests and disease control tests.

[0221] (Test of fungicidal effect against gray mold fungus) A spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was prepared. The pyrazole compound of the present invention was added to dimethyl sulfoxide to obtain a drug solution. This drug solution and the spore suspension were mixed in equal volumes (by volume) to obtain a test solution in which the pyrazole compound of the present invention was concentrated at 25 ppm by volume. The test solution was dropped onto a 96-well microplate (drug-treated group). Dimethyl sulfoxide and the spore suspension were mixed in equal volumes (by volume) to obtain a control solution. The control solution was dropped onto a 96-well microplate (untreated group). These were incubated at 20°C in the dark for 5 days. Turbidity OD at a wavelength of 405 nm was measured using a microplate reader. The growth inhibition rate was calculated using the following formula. Growth inhibition rate (%) = 100 - 100 × {[(OD of drug-treated group after culturing) - (OD of drug-treated group before culturing)] / [(OD of untreated group after culturing) - (OD of untreated group before culturing)]}

[0222] Fungicide efficacy tests were conducted on compounds numbered 1-6, 8-31, 33, 35-43, A-1-A-27, A-29-A-43, and A-45-A-52 against gray mold fungus. These compounds showed a growth inhibition rate of 75% or more.

[0223] (Fungicide efficacy test against grape blight fungus) The spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was replaced with a spore suspension of grape blight fungus (Glomerella cingulata, Vogel medium), and the temperature and duration of the standing period were changed to 25°C and 3 days, respectively. Turbidity was measured in the same manner as in the fungicide efficacy test against gray mold fungus, and the growth inhibition rate was calculated.

[0224] The fungicidal efficacy of compounds numbered 1-43 and A-1-A-52 against grape late blight fungus was tested. These compounds showed a growth inhibition rate of 75% or more.

[0225] (Fungicide efficacy test against apple anthracnose fungus) Turbidity was measured and the growth inhibition rate was calculated using the same method as in the fungicide efficacy test against gray mold fungus, except that the spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was replaced with a spore suspension of apple anthracnose fungus (Colletotrichum acutatum, Czapek medium), and the temperature and duration of the standing period were changed to 25°C and 4 days.

[0226] The fungicidal efficacy tests against apple anthracnose fungus were conducted for compounds numbered 1-6, 8-33, 35-43, A-1-A-27, A-29-A-36, A-38-A-43, and A-45-A-52. These compounds showed a growth inhibition rate of 75% or more.

[0227] (Fungicide efficacy test against apple leaf spot fungus) The spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was replaced with a spore suspension of apple leaf spot fungus (Alternaria mali, YBA medium), and the temperature and duration of the standing period were changed to 25°C and 4 days, respectively. Turbidity was measured in the same manner as in the fungicide efficacy test against gray mold fungus, and the growth inhibition rate was calculated.

[0228] Fungicide efficacy tests were conducted against apple leaf spot fungus for compounds numbered 1-6, 8-31, 33, 35-43, A-1-A-6, A-8-A-27, A-29-A-43, A-45-A-48, and A-50-A-52. These compounds showed growth inhibition rates of 75% or more.

[0229] (Control test for cucumber gray mold disease) Five parts by mass of the pyrazole compound of the present invention, 93.5 parts by mass of N,N-dimethylformamide, and 1.5 parts by mass of polyoxyethylene sorbitan monolaurate were mixed to obtain an emulsion (1) containing 5% by mass of the active ingredient.

[0230] Water was added to the emulsion (1) to obtain a chemical solution in which the pyrazole compound of the present invention was concentrated at 125 ppm by mass. Subsequently, the chemical solution was sprayed onto cucumber seedlings (variety "Jibai" type, cotyledon stage) cultivated in seedling pots, and then air-dried. After that, a conidial suspension of Botrytis cinerea, the fungus that causes cucumber gray mold, was inoculated onto the seedlings by drop (treated group). As a control, a conidial suspension of Botrytis cinerea, the fungus that causes cucumber gray mold, was inoculated onto cucumber seedlings that had not been sprayed with the chemical solution (untreated group). These were left standing in a humid chamber at 20°C. Four days after inoculation, the leaves of the cucumber seedlings were visually observed, and the control value was calculated from the diseased area percentage using the following formula.

[0231] Control effectiveness (%) = 100 - {Percentage of lesion area in treated area / Percentage of lesion area in untreated area} × 100

[0232] Control tests for cucumber gray mold were conducted on compounds numbered 1-6, 8-29, 31, 35, 37, 38, 40-43, A-1-A-6, A-8-A-13, A-15-A-18, A-20-A-24, A-26, A-27, A-29, A-30, A-35-A-42, A-45, A-48, A-49, and A-52. These compounds showed control efficacy of 75% or more.

[0233] (Control test for apple scab disease) Water was added to the emulsion (1) above so that the concentration of the pyrazole compound of the present invention was 125 ppm by mass, and the solution was dissolved to obtain a chemical solution. Subsequently, the chemical solution was sprayed onto apple seedlings (variety "Ohrin", 3-4 leaf stage) grown in seedling pots, and then air-dried. After that, conidia of the apple scab fungus (Venturia inaequalis) were inoculated onto these (treated group). As a control, apple seedlings that were not sprayed with the chemical solution were similarly inoculated (untreated group). These were then placed in a humid chamber at 20°C with alternating light and dark cycles every 12 hours. Twelve to fourteen days after inoculation, the leaves of the apple seedlings were visually observed, and the control value was calculated from the disease area percentage using the formula used to calculate the control value in the cucumber gray mold control test described above.

[0234] Control tests for apple scab were conducted on compounds numbered 1-4, 8-12, A-1-A-5, A-7, A-11, A-18, and A-21-A-23. These compounds showed control efficacy of 75% or more.

[0235] (Control test for wheat powdery mildew) Water was added to the emulsion (1) above so that the concentration of the pyrazole compound of the present invention was 125 ppm by mass, and the mixture was dissolved to obtain a chemical solution. Subsequently, the chemical solution was sprayed onto wheat seedlings (variety "Chihoku", 1-2 leaf stage) cultivated in seedling pots and air-dried. After that, conidia of the wheat powdery mildew fungus (Erysiphe graminis f.sp. tritici) were sprinkled on them and inoculated (treated group). As a control, wheat seedlings that were not sprayed with the chemical solution were sprinkled with conidia of the wheat powdery mildew fungus (Erysiphe graminis f.sp. tritici) and inoculated (untreated group). These were left standing in a greenhouse at 20°C. Six days after inoculation, the leaves of the wheat seedlings were visually observed, the disease area percentage was determined, and the control value was calculated in the same manner as in the previous test.

[0236] Control tests for wheat powdery mildew were conducted on compounds numbered 1-4, 6, 8-12, 14-17, A-1-A-6, A-9-A-13, A-15, A-18, A-21-A-23, and A-35. These compounds showed control efficacy of 75% or more.

[0237] Compound (I) in this embodiment is preferably one of the compounds shown in Table 8, and more preferably one of the compounds shown in Table 9.

[0238]

[0239]

[0240]

[0241] The compound (Ia) of this embodiment is preferably one of the compounds shown in Table 10, and more preferably one of the compounds shown in Table 11.

[0242]

[0243]

[0244]

[0245] The pyrazole compounds of the present invention have excellent fungicidal activity against pathogenic fungi that affect agricultural and horticultural plants, are highly safe, and can be synthesized industrially advantageously. The fungicides of the present invention can effectively control diseases of agricultural and horticultural plants.

Claims

A compound represented by formula (Z-I) or a salt thereof. [In the above formula (Z-I), Q １ This represents a substituted or unsubstituted 5-6 membered heterocyclyl group, or a substituted or unsubstituted 9-10 membered heterocyclyl group. Q ２ This represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a substituted or unsubstituted 9-10 membered heterocyclyl group. R １ This represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group. R ２ This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a cyano group, or a halogeno group. Z ａ This indicates an oxygen atom or a sulfur atom. Z represents an oxygen atom or a sulfur atom. R ６ This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a formyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. V is an oxygen atom, or formula: C(R ７ )(R ８ The group represented by ) is shown, R ７ represents a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 member heterocyclyl group, or a halogeno group, and R ８ This represents a hydrogen atom, a C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group. R ４ Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group. R ５ Each of these independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, or a halogeno group. R on the same carbon atom ４ and R ５ These may combine to form a divalent organic group. n represents an integer between 0 and 3. The compound or a salt thereof according to claim 1, wherein the above formula (Z-I) is represented by formula (I). [In the above formula (I), Q １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ , R ７ , R ８ and n are Q in the above formula (Z-I). １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ , R ７ , R ８ This has the same meaning as "and n". The compound or salt thereof according to claim 1, wherein the above formula (Z-I) is represented by formula (Ia). [In the above formula (Ia), Q １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ and n are Q in the above formula (Z-I). １ Q ２ Z ａ Z, R １ , R ２ , R ４ , R ５ , R ６ This has the same meaning as "and n". The compound according to claim 2 or a salt thereof, wherein the compound represented by formula (I) is one of the compounds listed in Table 1 below. The compound according to claim 2 or a salt thereof, wherein the compound represented by formula (I) is one of the compounds listed in Table 2 below. The compound according to claim 3 or a salt thereof, wherein the compound represented by formula (Ia) is any of the compounds listed in Table 3 below. The compound according to claim 3 or a salt thereof, wherein the compound represented by formula (Ia) is any of the compounds listed in Table 4 below. 　 A fungicide for agricultural and horticultural use, comprising at least one selected from the group consisting of the compounds and salts described in any one of claims 1 to 3 as an active ingredient. 　 A fungicide for agricultural and horticultural use according to claim 8, for use in seed treatment. 　 Furthermore, the fungicide for agricultural and horticultural use according to claim 8, further comprising other active ingredients. 　 Other active ingredients include nucleic acid biosynthesis inhibitors, mitosis inhibitors, cell division inhibitors, respiratory inhibitors, amino acid and protein synthesis inhibitors, signal transduction inhibitors, lipid and cell membrane synthesis inhibitors, cell membrane sterol biosynthesis inhibitors, cell wall synthesis inhibitors, melanin biosynthesis inhibitors, host plant resistance inducers, multi-site agents, biologics with multiple mechanisms of action, acetylcholinesterase inhibitors, GABAergic chloride ion channel blockers, sodium channel modulators, nicotinic acetylcholine receptor competitive modulators, nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride ion channel allosteric modulators, juvenile hormone analogs, nonspecific inhibitors, trepanic organ TRPV channel modulators, mite growth inhibitors, and microbial insect midgut endometrial disruptors. A fungicide for agricultural and horticultural use according to claim 10, which is at least one selected from the group consisting of a destructor, a mitochondrial ATP synthase inhibitor, an oxidative phosphorylation uncoupling agent that disrupts the proton gradient, a nicotinic acetylcholine receptor channel blocker, a chitin biosynthesis inhibitor type 0, a chitin biosynthesis inhibitor type 1, a molting inhibitor, a molting hormone receptor agonist, an octopamine receptor agonist, a mitochondrial electron transport chain complex III inhibitor, a mitochondrial electron transport chain complex I inhibitor, a voltage-gated sodium channel blocker, an acetyl-CoA carboxylase inhibitor, a mitochondrial electron transport chain complex IV inhibitor, a mitochondrial electron transport chain complex II inhibitor, a ryanodine receptor modulator, a choroid organ modulator with an unspecified target site, and a GABAergic chloride ion channel allosteric modulator. 　 The other active ingredients mentioned above are, Benalaxyl, Benalaxyl-M, Flalaxyl, Metalaxyl, Metalaxyl-M, Oxadixyl, Chlodilacon, Offlace; Bupirimate, dimethylmol, ethimol; Himexazole, octylinone; Oxolinic acid; Ipflufenoquin, quinofumelin; Benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, etaboxam; Pencyclon; Fluopicolide, fluopimamide; Phenamacril, metraphenone, pyriophenone; Pyridaclomethyl; Diflumetrim, Tolfenpyrad, Fenazaquin; Benodanil, Flutolanil, Mepronil, Isofetamide, Fluopyram, Cyclobtrifluram, Fenflam, Flumecyclox, Carboxyne, Oxycarboxyne, Tifluzamide, Benzovindiflupir, Bixafen, Fluxapyroxad, Flamethopyr, Isopyrazam, Penflufen, Penthiopyrad, Sedaxane, Boscalid, Pidiflumetofen, Isoflucipram, Pyraziflumid, Impilfluxam; Azoxystrobin, chemoxystrobin, cmethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxime-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidon, pyribencarb, methyltetraprole, mandestrobin; Cyazofamide, amisulbrom, fenpicoxamide, florylpicoxamide; Binapacril, Meptilzinocup, Zinocup, Fluazinam; Fentin acetate, fentin chloride, fentin hydroxide; Silthiofam; Ametoctradin; Andprim, Cyprodinil, Mepanipyrim, Pyrimethanil; Blastocydin-S, Kasugamycin, Kasugamycin hydrochloride, Streptomycin, Oxytetracycline; Tababolol; Quinoxifen, proquinazide; Fenpiclonil, fludioxonil, clozolinate, dimethacron, iprodione, procymidone, vinclozolin; Edifenfos, iprobenfos, pyrazofos, isoprothiolane; Biphenyl, chloreneb, dichlorane, quintozen, technazen, tolclophosmethyl, etridiazole; Iodocarb, propamocarb, propamocarb hydrochloride, propamocarb focetilate, prothiocarb; Extract of Goseikajeput; Natamycin; Triforine, Pyriphenox, Pyrisoxazole, Fenalimol, Flurprimidol, Nualimol, Imazalil, Imazalil sulfate, Oxpoconazole, Oxpoconazole fumarate, Pefurazoate, Prochloraz, Triflumizole, Viniconazole, Azaconazole, Vitertanol, Bromconazole, Cyproconazole, Diclobutrazol, Difenoconazole, Diniconazol, Diniconazol-M, Epoxyconazole, Etaco Nazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, mycrobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; Algimorph, Dodemorph, Dodemorph acetate, Fenpropimorph, Tridemorph, Fenpropidine, Piperalin, Spiroxamine; Fenhexamide, fenpyrazamine; Pyributicarb, naphthifine, terbinafine; Polyoxin, polyoxolim; Dimethomorph, Fulmorph, Pyrimorph, Benciavalicarb, Benciavalicarb isopropyl, Iprovalicarb, Valifenarate, Mandipropamide; Phthalide, pyroquilon, tricyclazole; Carpropamide, diclocimet, phenoxanil; Tolprocarb; Acibenzoral-S-methyl, probenazole, thiadinyl, isothianil, dicloventiazox; Ipfentrifluconazole, laminarin, Japanese knotweed extract; fosetyl aluminum, fosetyl calcium, fosetyl sodium, phosphoric acid, phosphate, phosphorous acid, phosphate; Cymoxanil, tecrophthalam, triazoxide, furusulfamide, diclomedin, cyflufenamide, dozin, dozin free base, fluthianil, ferimzon, tebufloxin, picarbtrazox, validamycin; Copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Ambam, Farbam, Mancozeb, Maneb, Mancapper, Methylam, Methylam zinc, Polycarbamate, Propineb, Thiram, Zineb, Ziram; Captan, Captafoll, Forpet, Chlorothalonil, Diclofluanide, Tollfluanide, Guazatin, Guazatin acetate, Iminoctadine triacetate, Iminoctadine trialbesylate, Anilazine, Dithianone, Quinomethionate, Fluorimide, Metasulfocarb; DBEDC, Fluorofolpet, Bis(8-Quinolinolate)copper(II), Propamidine, Chloropicrin, Cyproflam, Agrobacterium, Bethoxazine, Diphenylamine, Methylisothiocyanate (MITC), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumetobel, Irmamycin, Nitrotar Isopropyl, Oxamocarb, Pyrrolenitrin, Torniphanide, Zarilamid, Algophase, Amicalthiazole, Oxathiapiproline, Fluoxapiproline, Benzazole, Triclamide, Uniconazole, Oxyphenthiin, Pirapropoin, Fluindapyr, Aminopyrifene, Dipimethitrone, Fluphenoxadiazam, Flumethylsulforim, Feneptamidocine; Trichoderma atroviride I-1237 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride LU132 strain, Trichoderma atroviride SC1 strain, Trichoderma atroviride SKT-1 strain, Trichoderma atroviride 77B strain; Trichoderma aspererum T34 strain, Trichoderma aspererum kd strain; Trichoderma halzianum T-22 strain; Trichoderma virens G-41 strain; Kuro Nostachys rosea J1146 strain, Chronostachys rosea CR-7 strain; Coniotilium minitans CON / M / 91-08 strain; Hanseniaspora ubaraum BC18Y strain; Talaromyces flavus SAY-Y-94-01 strain; Saccharomyces cerevisiae LAS02 strain, Saccharomyces cerevisiae DDSF623 strain; Bacillus amyloriquefaciens QST713 strain, Bacillus amyloriquefaciens FZB24 strain, Bacillus amyloliquefaciens MBI600 strain, Bacillus amyloliquefaciens D747 strain, Bacillus amyloliquefaciens F727 strain, Bacillus amyloliquefaciens AT-332 strain; Bacillus subtilis AFS032321 strain, Bacillus subtilis Y1336 strain, Bacillus subtilis HAI-040 4 strains: Bacillus subtilis RTI477; Bacillus berezensis RTI301; PHC25279; Gluconobacter serinas BC18B; Pseudomonas chlororaffis ASF009; Pseudomonas rhodesia HAI-0804; Streptomyces griseobilides K61; Streptomyces riddix WYEC108; Alanicarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimicarb, Propoxul, Thiodicarb, Thiofanox, Triazamate, Trimetacarb, XMC, Xylylcarb; Phenothiocarb, MIPC, MPMC, MTMC, Aldoxycarb, Alixicarb, Aminocarb, Bufencarb, Chloetocarb, Metam sodium, Promecarb; Acephate, Azamethiphos, Adinphos-ethyl, Adinphos-methyl, Kazsaphos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos, Diclotophos, Dimethoate, Dimethylvinphos, Disulfon, EPN, Ethion, Etoprophos, Fanflu, Phenamiphos, Fenitrothion, Fenthion, Fostiazate, Heptenophos, Imisiaphos, Isofenphos, Isocarbophos, Isopropyl-O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Metamidophos, Methidathion, Mevinphos, Monoclotophos, Nared, Omethoate, Oxydimethone-methyl, Parathion, Para Thione methyl, fenthoate, phorate, fosalon, fosmet, phosphamidone, foxim, pyrimiphos methyl, profenofos, propetamfos, prothiofos, pyraclofos, pyridaphenthion, quinalfos, sulfotep, tebupyrimfos, temefos, terbufos, tetrachlorvinfos, thiometon, triazofos, trichlorfon, bamidothion, bromophos ethyl, BRP, carbophenothion, cyanophenfos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzofos, etrimfos, fensulfothion, flupyrazofos, honofos, formothion, fosmetylane, isazofos, iodophenfos, methacryfos, pyrimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos; Chlordane, endosulfan, ethiprole, fipronil; acetoprole, pyrafluprole, pyriprole, campechlor, heptachlor, dienochlor, flufiprol; Acrinatrin, allethrin, d-cistrans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, biorethmetrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin Lumethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, cadesrin, permethrin, phenothrin Phosphorus [(1R)-trans isomer], prallethrin, pyrethram, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioetanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metofluthrin, protrefenbut, pyrethmethrin, terarethrin, κ-bifenthrin, chloroprarethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioetanomethrin; DDT, methoxychloride; Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradiflon, dichloromesothiaz, fenmesoditiaz, triflumesopyrim, flupyrim; Spinetorum, Spinosad; Abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin; Hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen; diofenolan, epophenonane, triprene; 1,3-Dichloropropene, methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartaric acid, dazomet, metam, potassium metam, sodium metam; Pymetrozine, pyrifluquinazon, afidopiropen; Clofentezine, diflovidazine, hexythiazox, etoxazole; Proteins contained in Bacillus thuringiensis subspecies islaerensi, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies krustaki, Bacillus thuringiensis subspecies tenebryonis, Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus; Diafenthiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargit, tetradiphon; Chlorfenapir, DNOC, sulfuramide; Binapacril, Dinobuton, Dinocup; Bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt; nereistoxin; Bistriflurone, Chlorfluazurone, Diflubenzuron, Flucycloxurone, Flufenoxurone, Hexaflumurone, Lufenuron, Novalon, Noviflumurone, Teflubenzuron, Triflumurone; Buprofezin, Fluazurone; Buprofezin; Cyromazine; Chromafenozide, halofenozide, methoxyfenozide, tebufenozide; Amitraz; Demiditraz, Chlordimeform; Hydramethylnon, acequinosyl, fluacrypyrim, bifenazate; Phenazaquine, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; Indoxacarb, metaflumizone; Spidoxamat, spirodiclofen, spiromesifen, spiropidione, spirotetramat; Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide; cyenopyrafen, cyflumetofen, piflubumide; Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamid, tetraniliprole; tetrachlorantraniliprole; flonicamide; Fluxamethamide, isocycloceram, brofuranilide; afoxolaner, fluralaner, rotineral, sarolaner; Asinonapil, Frometkin, Redoprona, Zinpropyridaz, Oxazosulfyl, Azadirachtin, Benzoximate, Benzpyrimoxane, Bromopropate, Quinomethionate, Dicofor, Lime sulfur mixture, Mancozeb, Pyridaryl, Sulfur; Cryolite, Bencrothiaz, Amidoflumet, DCIP, Phenisobromolate, Benzomate, Metaldehyde, Chlorbenzilate, Clothiazoben, Dicyclanil, Phenoxacrim, Fentriphanil, Flubenzimine, Fluphenazine, Gossiplua, Japonilua, Methoxadiazone, Petroleum (oil), Potassium Oleate, Tetrasul, Triaracene, Afidopiropene, Flufiprol, Fluensulfol Meperflusrin, tetramethylflusrin, tralopyril, dimeflusrin, methylneodecanamide, broflanilide, Steiner's nema capocapsae, Steiner's nema glacerai, Pastouria penetrans, Pechylomyces stenuipes, Pechylomyces phmosoroseus, Beauveria bassiana, Beauveria bronniati, Metallidium anisoplie, Verticillium lecani, fulhexaphon, cyclopyrazoflor; Fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambendazole; Closantel, oxyclozanide, lafoxanide, niclosamide; Nitroxynyl, nitroscanate; Pyranter, Moranter; Lebamisol, Tetramisol; Praziquantel, Epsiplantel; Cyclodiene, Lianya, Chlorthrone, Metronidazole, Demiditraz, Piperazine, Diethylcarbamazine, Dichlorophene, Monepantel, Tribenzimidine, Amidantel, Thiacetalthamide, Melalsomine, Arsenamide; Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazurone, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetylaminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1-naphthylacetamide, etichlor The agricultural and horticultural fungicide according to claim 10, which is at least one selected from the group consisting of zete, cloxifonac, hydrazide maleate, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobancol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, etephon, chlormecoat, mepicote chloride, benzyladenine, 5-aminolevulinic acid, and daminozide. A compound represented by formula (im-3A) or a salt thereof. [In the above formula (im-3A), Q １ａ This indicates a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted thiazolyl group. R １ This represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group. R ２ This represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a cyano group, or a halogeno group. U represents a halogen group, a hydroxyl group, or a C1-6 alkoxy group.

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