Triazole compound and microbicide for agricultural or horticultural use

Abstract

The present invention is a compound represented by formula (Z-I) or a salt thereof. (In the formula: Q1 and Q2 each represent a phenyl group or the like; B1, B2, and B3 each represent a nitrogen atom or a group represented by NR1, but among B1, B2, and B3, one of them is a group represented by NR1, and the remaining two are nitrogen atoms; R1 represents an alkyl group or the like; Za represents an oxygen atom or the like; T represents a partial structure (T-1) or (T-2); Z represents an oxygen atom or the like; R6 represents a hydrogen atom or the like; Zb represents an alkoxy group or the like; R7 and R8 each represent a hydrogen atom or the like; R4 and R5 each represent a hydrogen atom or the like; and n represents an integer of 0 to 3.)

Description

Triazole compounds and agricultural and horticultural fungicides

[0001] The present invention relates to a triazole compound and an agricultural and horticultural fungicide. More specifically, the present invention relates to a triazole compound that has excellent fungicidal activity against pathogens that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously, and to an agricultural and horticultural fungicide containing the same as an active ingredient. This application claims priority based on Japanese Patent Application No. 2024-054415 filed in Japan on March 28, 2024, Japanese Patent Application No. 2024-103172 filed in Japan on June 26, 2024, and Japanese Patent Application No. 2024-188193 filed in Japan on October 25, 2024, the contents of which are incorporated herein by reference.

[0002] Various compounds have been proposed that have fungicidal activity against pathogens that affect agricultural and horticultural plants. In order for such compounds to be practically used as agricultural and horticultural fungicides, they must not only have sufficiently high efficacy but also be unlikely to develop fungicide resistance, not cause phytotoxicity to plants or soil contamination, and have low toxicity to livestock, fish, etc.

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

[0004]

[0005] International Publication No. 2023 / 243678

[0006] An object of the present invention is to provide a triazole compound which has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially in an advantageous manner, and to provide an agricultural and horticultural fungicide containing the same as an active ingredient.

[0007] As a result of intensive investigations aimed at solving the above problems, the present invention has been completed, including the following aspects: (1) A compound represented by formula (ZI) or a salt thereof.

[0008]

[0009] [wherein in the formula (Z-I), Q １represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and a partial structure of the following formula (III):

[0010]

[0011] In B １ is a nitrogen atom or a group of the formula: NR １ B represents a group represented by ２ is a nitrogen atom or a group of the formula: NR １ B represents a group represented by ３ is a nitrogen atom or a group of the formula: NR １ B represents a group represented by １ , B ２ , and B ３ wherein one of the formulas is NR １ and the remaining two are nitrogen atoms, and R １ each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, the carbon atoms marked with * and + in the partial structure of formula (III) correspond to the carbon atoms marked with * and + in formula (Z-I), and Z ａ represents an oxygen atom or a sulfur atom, T represents the partial structure (T-1) or the partial structure (T-2),

[0012]

[0013] In the partial structure (T-1) or partial structure (T-2), the arrow marked with + is bonded to the carbon atom marked with + in the partial structure of formula (III), and the other arrow is bonded to the carbon atom marked with + in formula (Z-I). ７ and R ８ In the partial structure (T-1), Z represents an oxygen atom or a sulfur atom, and R ６represents 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 heterocyclyl group, ｂ represents a C1-6 alkoxy group or a C1-6 alkylthio group, 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 heterocyclyl group, or a halogeno group; R ８ 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 heterocyclyl group, or a halogeno group; R 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- or 6-membered heterocyclyl group, or a halogeno group; R ５ each independently represent 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- or 6-membered heterocyclyl group, or a halogeno group, and R ４ and R５ may combine with each other to form a divalent organic group, and n represents an integer of 0 to 3.] (2) The compound or salt thereof according to (1), wherein formula (Z-I) is represented by formula (I).

[0014]

[0015] [wherein in the formula (I), Q １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ , R ８ and n is Q in formula (Z-I). １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ , R ８ and n have the same meaning as Z and R ６ represents Z and R in the partial structure (T-1). ６ (3) The compound or salt thereof according to (1), wherein formula (ZI) is represented by formula (II).

[0016]

[0017] [wherein in the formula (II), Q １ , Q ２ , Z ａ , R ４ , R ５ , R ７ , R ８ and n is Q in formula (Z-I). １ , Q ２ , Z ａ , R ４ , R ５ , R ７ , R ８ and n have the same meaning as R １ is R in the formula (III). １ and Z and R ６represents Z and R in the partial structure (T-1). ６ (4) An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compounds and salts thereof described in any one of (1) to (3). (5) The agricultural and horticultural fungicide described in (4) above, which is used for seed treatment. (6) The agricultural and horticultural fungicide described in (4) above, which further contains another active ingredient.

[0018] (7) The other active ingredients are nucleic acid biosynthesis inhibitors, mitosis inhibitors, cell division inhibitors, respiration 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, agents with multiple sites of action, biological preparations 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-activated chloride ion channel allosteric modulators, juvenile hormone analogs, non-specific inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial-derived insect midgut membrane disruptors. The agricultural and horticultural fungicide according to (6), which is at least one selected from the group consisting of a mitochondrial ATP synthase inhibitor, a mitochondrial ATP synthase inhibitor, an oxidative phosphorylation uncoupler that disrupts a proton gradient, a nicotinic acetylcholine receptor channel blocker, a chitin biosynthesis inhibitor type 0, a chitin biosynthesis inhibitor type 1, a molting inhibitor, an ecdysone receptor agonist, an octopamine receptor agonist, a mitochondrial electron transport chain complex III inhibitor, a mitochondrial electron transport chain complex I inhibitor, a voltage-dependent 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 chordotonal organ modulator with an unspecified target site, and a GABA-gated chloride ion channel allosteric modulator.

[0019] (8) The other active ingredients are benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, oflace; bupirimate, dimethirimol, ethirimol; hymexazole, octhilinone; oxolinic acid; ipflufenoquin, quinofumelin; benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, diethofencarb, zoxamide, ethaboxam; pencycuron; fluopicolide, fluopimomide; fenamacryl, metrafenone, pyriophenone; pyridaclomethyl; diflumetrim, tolfenpyrad, fenazaquin; Benodaniil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenfuram, flumecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pydiflumetofen, isoflucipram, pyraziflumid, inpirfluxam; Azoxystrobin, cumoxystrobin, methoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopiricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, methyltetraprole, mandestrobin; cyazofamid, amisulbrom, fenpicoxamide, florylpicoxamide; binapacryl, meptyldinocap, dinocap, fluazinam; fentin acetate, fentin chloride, fentin hydroxide; silthiofam; ametoctrazine; andoprim, cyprodinil, mepanipyrim, pyrimethanil; Blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline; tavaborole; quinoxyfen, proquinazide;Fenpiclonil, fludioxonil, chlozolinate, dimethaclon, iprodione, procymidone, vinclozolin; edifenphos, iprobenfos, pyrazophos, isoprothiolane; biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl, etridiazole; iodocarb, propamocarb, propamocarb hydrochloride, propamocarb focetylate, prothiocarb; extract of Goseikan; natamycin; Triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, biniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaco nazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; fenhexamid, fenpyrazamine; pyributicarb, naftifine, terbinafine; polyoxin, polyoxolim; dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthiavalicarb isopropyl, iprovalicarb, valifenalate, mandipropamid; fthalide, pyroquilon, tricyclazole; carpropamid, diclocymet, fenoxanil; tolprocarb; acibenzolar-S-methyl, probenazole, tiadinil, isotianil, diclobenthiazox; ipfentrifluconazole, laminarin, giant knotweed extract;Fosetyl aluminum, fosetyl calcium, fosetyl sodium, phosphoric acid, phosphate salts, phosphorous acid, phosphites; cymoxanil, tecloftalam, triazoxide, flusulfamide, diclomedine, cyflufenamid, dodine, dodine free base, flutianil, ferimzone, tebufloquine, picarbutrazox, validamycin; Copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Ambam, Ferbam, mancozeb, maneb, mancopper, metiram, metiram zinc, polycarbamate, propineb, thiram, zineb, ziram; Captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine tribesylate, anilazine, dithianone, chinomethionate, fluorimide, metasulfocarb; DBEDC, Fluorofolpet, Bis(8-quinolinolato)copper(II), Propamidine, Chloropicrin, Cyprofuram, Agrobacterium, Bethoxadin, Diphenylamine, Methylisothiocyanate (MITC), Mildeomycin, Capsaicin, Kufuraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Difenzoquat, Difenzoquat Methylsulfonate, Flumetober, Irmamycin, Nitrotarisopropyl, Oxamocarb, Pyrrolnitrin, Tolnifanide, Zaliramide, Argophase, Amicarthiazole, Oxathiapiproline, Fluoxapiproline, Benthiazole, Trichlamide, Uniconazole, Oxfenthiin, Pyrapropoin, Fluindapyr, Aminopyrifen, Dipimethitron, Flufenoxadiazam, Flumethylsulfolim, Feneptamidoquin; Trichoderma atroviride strain I-1237, Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1, Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B; Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum strain T-22; Trichoderma virens strain G-41;Clonostachys rosea strain J1146, Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON / M / 91-08; Hanseniaspora ubaraum strain BC18Y; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisiae strain LAS02, Saccharomyces cerevisiae strain DDSF623; Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens FZB24 strain, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332; Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis HAI-040 Four strains: Bacillus subtilis strain RTI477; Bacillus veresensis strain RTI301; PHC25279; Gluconobacter selinus strain BC18B; Pseudomonas chlororaphis strain ASF009; Pseudomonas rhodesiae strain HAI-0804; Streptomyces griseoviridis strain K61, and Streptomyces ridicus strain WYEC108; Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb; fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb;Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fenflur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isocarbophos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, para Thionemethyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, fonofos, formothion, fosmetilan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos; Chlordane, endosulfan, ethiprole, fipronil; acetoprole, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor, flufiprole;Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, 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, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, fenothrin phosphorus [(1R)-trans isomer], prallethrin, pyrethrum, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, telallethrin, κ-bifenthrin, chloroprallethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioethanomethrin; DDT, methoxychlor; acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradifurone, dichloromezothiaz, phenmezodithiaz, triflumezopyrim, flupirimine; spinetoram, spinosad; abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;Hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen; diofenolan, epofenonane, triprene; 1,3-dichloropropene, methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metam potassium salt, metam sodium salt; pymetrozine, pyrifluquinazone, afidopiropen; clofentezine, diflobidazine, hexythiazox, etoxazole; Bacillus thuringiensis subsp. israerensi, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, proteins found in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus; diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon; chlorfenapyr, DNOC, sulfluramide; binapacryl, dinobuton, dinocap; bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt; nereistoxin; Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron; buprofezin, fluazuron; buprofezin; cyromazine; chromafenozide, halofenozide, methoxyfenozide, tebufenozide; amitraz; demiditraz, chlordimeform; hydramethylnon, acequinocyl, fluacrypyrim, bifenazate; fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; indoxacarb, metaflumizone; spidoxamat, spirodiclofen, spiromesifen, spiropydione, spirotetramat;Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide; cyenopyrafen, cyflumetofen, piflubumid; chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetraniliprole; tetrachlorantraniliprole; flonicamid; fluxametamide, isocycloceram, brofuranilide; afoxolaner, fluralaner, lotineral, sarolaner; acinonapyr, flometoquin, ledoprona, zinzpropylidaz, oxazosulfil, azadirachtin, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, dicofol, lime sulfur, mancozeb, pyridalyl, sulfur; Cryolite, benclothiaz, amidoflumet, DCIP, phenisobromorate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossiplura, japonirua, methoxadiazone, petroleum oil, potassium oleate, tetrasulfur, triarane, afidopiropen, flufiprole, fluensulfo n, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, broflanilide, Steinernema carpocapsae, Steinernema glacerai, Pasteuria penetrans, Pecilomyces tenuipes, Pecilomyces fumosoroseus, Beauveria bassiana, Beauveria brongniartii, Metarhizium anisopliae, Verticillium lecanii, fluhexafon, cyclopyrazoflor; Fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambandazole; closantel, oxyclozanide, rafoxanide, niclosamide; nitroxynil, nitrosquanate; pyrantel, morantel; levamisole, tetramisole; praziquantel, epsiprantel;Cyclodiene, riania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, 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 abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothio (9) The agricultural and horticultural fungicide according to (6), which is at least one selected from the group consisting of benzoyl, 1-naphthylacetamide, ethychlozate, cloxifonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, and daminozide. (10) A compound represented by formula (im-1a) or a salt thereof.

[0020]

[0021] [In the formula (im-1a), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, U １ａ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.] (10) A compound represented by formula (im-2) or a salt thereof:

[0022]

[0023] [In the formula (im-2), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.] (11) A compound represented by formula (im-1aS) or a salt thereof:

[0024]

[0025] [In the formula (im-1aS), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, U １ａ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.] (12) A compound represented by the formula (im-2S) or a salt thereof:

[0026]

[0027] [wherein, Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.

[0028] The triazole compound of the present invention has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously. The agricultural and horticultural fungicide of the present invention can effectively control diseases of agricultural and horticultural plants.

[0029] The triazole compound of this embodiment is a compound represented by formula (ZI) (hereinafter, may be referred to as compound (ZI)) or a salt of compound (ZI).

[0030]

[0031] As used herein, the term "unsubstituted" refers to only the core group. When the name of the core group is used alone without the term "substituted," it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom in the core group has been replaced with a group (substituent) of the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The two or more substituents may be the same or different. A term such as "C1-6" indicates that the core group has 1 to 6 carbon atoms, for example. 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. The "substituent" is not particularly limited as long as it is chemically permissible and provides the effects of the present invention.

[0032] Examples of groups that can serve as "substituents" include: C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C2-6 alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl; C2-6 alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2-propynyl;

[0033] 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- to 6-membered heterocyclyl groups; 3- to 6-membered heterocyclyl C1-6 alkyl groups;

[0034] 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- to 6-membered heteroaryloxy groups such as thiazolyloxy and pyridyloxy groups; 5- to 6-membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy and pyridylmethyloxy groups;

[0035] a formyl group; a C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group; a formyloxy group; a C1-6 alkylcarbonyloxy group such as an acetyloxy group or a propionyloxy group; a benzoyl group; a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group or a t-butoxycarbonyl group; a C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group or a t-butoxycarbonyloxy group; a carboxyl group;

[0036] halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group, and a perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, and a 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as a chloroacetyl group, a trifluoroacetyl group, or a trichloroacetyl group;

[0037] amino groups; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino; anilino and naphthylamino groups; phenyl C1-6 alkylamino groups such as benzylamino and phenethylamino; formylamino groups; C1-6 alkylcarbonylamino groups such as acetylamino, propanoylamino, butyrylamino, and i-propylcarbonylamino; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, and i-propoxycarbonylamino; unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, and N-phenyl-N-methylaminocarbonyl; imino C1-6 alkyl groups such as iminomethyl, (1-imino)ethyl, and (1-imino)-n-propyl; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as an N-hydroxy-iminomethyl group, a (1-(N-hydroxy)-imino)ethyl group, a (1-(N-hydroxy)-imino)propyl group, an N-methoxy-iminomethyl group, or a (1-(N-methoxy)-imino)ethyl group; an aminocarbonyloxy group; a C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group or a dimethylaminocarbonyloxy group;

[0038] a mercapto group; a C1-6 alkylthio group such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, an s-butylthio group, or a t-butylthio group; a C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group; a phenylthio group or a naphthylthio group; a 5- or 6-membered heteroarylthio group such as a thiazolylthio group or a pyridylthio group;

[0039] 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- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl and pyridylsulfinyl groups;

[0040] C1-6 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl and 2,2,2-trifluoroethylsulfonyl groups; phenylsulfonyl groups; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl and pyridylsulfonyl groups; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy, ethylsulfonyloxy, and t-butylsulfonyloxy groups; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy and 2,2,2-trifluoroethylsulfonyloxy groups;

[0041] Tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; triphenylsilyl group; cyano group; and nitro group.

[0042] In addition, any hydrogen atom in these "substituents" may be substituted with a group of a different structure. In this case, examples of the "substituent" include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

[0043] Furthermore, the above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0044] Examples of the "3- to 6-membered saturated heterocyclyl group" include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

[0045] Examples of "5-membered heteroaryl groups" include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. Examples of "6-membered heteroaryl groups" include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups. Examples of "5- to 6-membered partially unsaturated heterocyclyl groups" include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl, dihydrofuranyl, dihydrothiophenyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, thiazolinyl, and isothiazolinyl groups; and 6-membered partially unsaturated heterocyclyl groups such as dihydropyranyl.

[0046] Q in formula (Z-I) １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9- or 10-membered heterocyclyl group.

[0047] Q in formula (Z-I) ２represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- or 6-membered heterocyclyl group, or a substituted or unsubstituted 9- or 10-membered heterocyclyl group.

[0048] A heterocyclyl group contains at least one heteroatom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. The heterocyclyl group may be either monocyclic or polycyclic. In a polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be saturated alicyclic, unsaturated alicyclic, or aromatic.

[0049] Q １ or Q ２ Examples of the "5- to 6-membered heterocyclyl group" in the above formula include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

[0050] Q １ or Q ２ Examples of the "5- to 6-membered saturated heterocyclyl group" in the above formula include a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydropyranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

[0051] Q １ or Q ２ Examples of the "5-membered heteroaryl group" in the above formula include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group.

[0052] Q １ or Q ２ Examples of the "6-membered heteroaryl group" in the above formula include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

[0053] Q １ or Q ２Examples of the "5- to 6-membered partially unsaturated heterocyclyl group" in the above formula (I) 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.

[0054] Q １ or Q ２ Examples of the "9-membered heterocyclyl group" in the above formula include an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a benzisothiazolyl group, and a benzodioxolanyl group.

[0055] Q １ or Q ２ Examples of the "10-membered heterocyclyl group" in the above formula include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.

[0056] Q １ or Q ２In the above, substituents on the "5- to 6-membered heterocyclyl group", "phenyl group", "naphthyl group" or "9- to 10-membered heterocyclyl group" include a halogeno group, a C1-6 alkyl group, a C1-6 alkenyl 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 alkylcarbonyl group, a C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C1-6 alkylsulfonyloxy group, a sulfonamido group, a C3-6 cycloalkyl group, a phenyl group, a phenyloxy group, a 5-membered heteroaryl group, a 6-membered heteroaryl group, an amino group, a cyano group, a nitro group, and a triC1-6 alkylsilyl group; An amino group substituted by a C1-6 alkyl group or a C1-6 alkylcarbonyl group; a carboxamido group substituted by a C1-6 alkyl group; a carboxamido group substituted by a C1-6 alkoxy group; a phenyl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a 6-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group.

[0057] Q １ or Q ２Two substituents on the "5- to 6-membered heterocyclyl group," "phenyl group," "naphthyl group," or "9- to 10-membered heterocyclyl group" in the above formula (I) may be taken together to form a divalent organic group, or two substituents on a phenyl group substituted with two substituents, a 5-membered heteroaryl group substituted with two substituents, or a 6-membered heteroaryl group substituted with two substituents may be taken together to form a divalent organic group. Examples of the divalent organic group include C3-6 alkylene groups such as trimethylene and tetramethylene; C1-3 alkylenedioxy groups such as methylenedioxy and dimethylenedioxy; and the like. For example, two substituents on a phenyl group may be taken together to form a trimethylene group, and Q １ or Q ２ It is preferred to form an indanyl group as follows.

[0058] Among these, Q in formula (Z-I) １ is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5-membered heterocyclyl group, a substituted or unsubstituted 6-membered heterocyclyl group, or a substituted or unsubstituted 9-membered heterocyclyl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrazolyl group, or a substituted or unsubstituted benzothiazolyl group, and even more preferably a substituted or unsubstituted phenyl group. １and the substituents on the "5- to 6-membered heterocyclyl group", "phenyl group", "naphthyl group" or "9- to 10-membered heterocyclyl group" in the above formula (I) are more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy 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 cyano group, a nitro group, or a triC1-6 alkylsilyl group; an amino group substituted with a C1-6 alkyl group or a C1-6 alkylcarbonyl group; and / or a carboxamide group substituted with a C1-6 alkyl; even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylthio group, a C3-6 cycloalkyl group, a cyano group, or a nitro group; and / or an amino group substituted with a C1-6 alkyl group, even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, or a cyano group. Among these, the substituent on the "phenyl group" is more preferably one or more of a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, or a cyano group, even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6 haloalkyl group, and even more preferably a halogeno group or a C1-6 haloalkyl group. The substituent on the "6-membered heterocyclyl group" is more preferably a halogeno group. Q １ When the "5- to 6-membered heterocyclyl group", "phenyl group", "naphthyl group" or "9- to 10-membered heterocyclyl group" in has a substituent, the number of the substituent is preferably 1 or 2, and more preferably 1. １ may represent an indanyl group in which two substituents on the phenyl group are taken together to form a trimethylene group.

[0059] Q in formula (Z-I) ２Q more preferably represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzothiazolyl group, or a substituted or unsubstituted quinolinyl group, and even more preferably represents a substituted or unsubstituted phenyl group. ２ The substituents on the "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group", or "9- to 10-membered heterocyclyl group" in the formula (I) are more preferably a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 alkoxy group substituted with a C1-6 alkoxy group, a cyano group; or an amino group substituted with a C1-6 alkyl group; ２ In the above, the substituent on the "phenyl group" or "naphthyl group" is even more preferably a halogeno group, a C1-6 alkyl group, a C1-6 alkoxy group, or a cyano group, even more preferably a halogeno group or a C1-6 alkyl group, and even more preferably a C1-6 alkyl group; and the substituent on the "5- or 6-membered heterocyclyl group" or "9- or 10-membered heterocyclyl group" is even more preferably a C1-6 alkyl group or a C1-6 alkoxy group. Q ２ When the "phenyl group", "naphthyl group", "5- to 6-membered heterocyclyl group" or "9- to 10-membered heterocyclyl group" in Q has a substituent, the number of the substituents is preferably 1 or 2, and more preferably 2. ２ may represent an indanyl group in which two substituents on the phenyl group are taken together to form a trimethylene group.

[0060] Each symbol in the partial structure of the following formula (III) has the following meaning.

[0061]

[0062] The carbon atoms marked with * and + in the partial structure correspond to the carbon atoms marked with * and + in formula (Z-I). １ is a nitrogen atom or a group of the formula: NR １ represents a group represented by the formula: ２is a nitrogen atom or a group of the formula: NR １ represents a group represented by the formula: ３ is a nitrogen atom or a group of the formula: NR １ where B represents a group represented by １ , B ２ , and B ３ wherein one of the formulas is NR １ and the remaining two are nitrogen atoms.

[0063] Specific examples of the partial structure of formula (III) include the following:

[0064]

[0065] R １ each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, and preferably represents a substituted or unsubstituted C1-6 alkyl group.

[0066] R １ The "C1-6 alkyl group" in the formula may be a straight chain or a branched chain. １ Examples of the "C1-6 alkyl group" in the above formula 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, and the like.

[0067] R １ Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0068] R １In the above, examples of the substituent on the "C1-6 alkyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups, hydroxyl groups, C1-6 alkoxy groups such as 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; phenyl groups substituted by one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups; A 5-membered heteroaryl group substituted by 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 by 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, with one or more of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group being more preferred.

[0069] R １ In the above, the substituents on the "C3-6 cycloalkyl group" 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 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.

[0070] The partial structure of the formula (III) is preferably the partial structure of the formula (III-1).

[0071] Z in formula (Z-I) ａ represents an oxygen atom or a sulfur atom. ａ is preferably an oxygen atom.

[0072] T in formula (ZI) represents the partial structure (T-1) or the partial structure (T-2).

[0073]

[0074] In the partial structures (T-1) and (T-2), the arrow with + sign is bonded to the carbon atom with + sign in the partial structure of the formula (III), and the other arrow is bonded to the carbon atom with R ７ and R ８ is bonded to a carbon atom having

[0075] Z in the partial structure (T-1) represents an oxygen atom or a sulfur atom, and preferably represents an oxygen atom.

[0076] R in partial structure (T-1) 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 heterocyclyl group, preferably a hydrogen atom.

[0077] R ６ The "substituted or unsubstituted C1-6 alkyl group" and "substituted or unsubstituted C3-6 cycloalkyl group" in １ The same examples as those given above can be mentioned.

[0078] R ６Examples of the "C2-6 alkenyl group" in the above formula 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.

[0079] R ６ Examples of the "C2-6 alkynyl group" in the above formula 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, 1,1-dimethyl-2-butynyl group, and the like.

[0080] R ６ Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, an n-propylcarbonyl group, an i-propylcarbonyl group, an n-butylcarbonyl group, and a t-butylcarbonyl group.

[0081] R ６ Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.

[0082] R ６In the above, examples of the substituents on the "C2-6 alkenyl group," "C2-6 alkynyl group," "C1-6 alkylcarbonyl group," and "C1-6 alkoxycarbonyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups, hydroxyl groups, C1-6 alkoxy groups such as 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; phenyl groups substituted by one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups; A 5-membered heteroaryl group substituted by 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 by 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, with one or more of a halogeno group, a C1-6 alkoxy group, or a C3-6 cycloalkyl group being more preferred.

[0083] R ６ The "5- to 6-membered heterocyclyl group" in the above formula (I) is a group containing, as ring-constituting atoms, 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group; a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isoxazolinyl group; and a dihydropyranyl group, with a pyrazolinyl group being preferred.

[0084] R ６In the above, substituents on the "phenyl group", "naphthyl group", and "5- to 6-membered heterocyclyl group" include 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, and 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 selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group is preferred, and a halogeno group is more preferred.

[0085] Among these, R in the partial structure (T-1) ６ is preferably a hydrogen atom or an unsubstituted C1-6 alkyl group, more preferably a hydrogen atom.

[0086] In the partial structure (T-2), Z ｂ represents a C1-6 alkoxy group or a C1-6 alkylthio group.

[0087] Z ｂ Examples of the "C1-6 alkoxy group" in the above formula include 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, and a t-butoxy group.

[0088] Z ｂ Examples of the "C1-6 alkylthio group" in the above formula include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and an i-butylthio group.

[0089] Among these, Z in the partial structure (T-2) ｂ is preferably a methoxy group or a methylthio group.

[0090] Among these, it is preferable that T in formula (ZI) represents the partial structure (T-1).

[0091] R in formula (Z-I) 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 heterocyclyl group, or a halogeno group.

[0092] R in formula (Z-I) ８ 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 heterocyclyl group, or a halogeno group.

[0093] R ７ and R ８ Examples of the "halogeno group" in R include a fluoro group, a chloro group, a bromo group, and an iodo group. ７ and R ８ In the above, "C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", and "substituted or unsubstituted 5- to 6-membered heterocyclyl group" are R １ and R ６ The same examples as those given above can be mentioned.

[0094] Among these, R in formula (Z-I) ７ and R ８ are each independently preferably a hydrogen atom or a C1-6 alkyl group, more preferably a hydrogen atom.

[0095] R in formula (Z-I) ４each 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- or 6-membered heterocyclyl group, or a halogeno group.

[0096] R in formula (Z-I) 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- or 6-membered heterocyclyl group, or a halogeno group.

[0097] R ４ and R ５ In the above, "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted C3-6 cycloalkyl group", "substituted or unsubstituted phenyl group", "substituted or unsubstituted naphthyl group", "substituted or unsubstituted 5- to 6-membered heterocyclyl group", and "halogeno group" are R １ , R ６ , R ７ and R ８ The same examples as those given above can be mentioned.

[0098] R on the same carbon atom ４ and R ５ may combine with each other to form a divalent organic group. Examples of the divalent organic group include C2-5 alkylene groups such as dimethylene, trimethylene, and tetramethylene.

[0099] Among these, R in formula (Z-I) ４ and R ５ Preferably, each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a halogeno group.

[0100] n is the number of repetitions of the structural unit in [ ] and represents an integer of 0 to 3, preferably an integer of 1 to 3. n is preferably 1 or 2, more preferably 1. Alternatively, n is preferably 0.

[0101] The triazole compound of this embodiment is preferably a compound represented by formula (I) (hereinafter, may be referred to as compound (I)) or a salt thereof. Each symbol in formula (I) has the same meaning as in formula (Z-I).

[0102]

[0103] An example of the triazole compound of this embodiment is a compound represented by the following formula (II) or a salt thereof. Each symbol in formula (II) has the same meaning as in formula (Z-I).

[0104]

[0105] The salt of compound (Z-I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples of the salt 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.

[0106] 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 a known production method described in the Examples, etc. Furthermore, a salt of compound (Z-I) can be obtained from compound (Z-I) by a known method.

[0107] The agricultural and horticultural fungicide of this embodiment contains at least one active ingredient selected from the group consisting of compound (Z-I) and a salt of compound (Z-I) (hereinafter, sometimes referred to as active ingredient (Z-I)). The amount of active ingredient (Z-I) contained in the agricultural and horticultural fungicide of this embodiment is not particularly limited as long as it exhibits a fungicidal effect.

[0108] Production Intermediates The compound represented by the following formula (im-1a) or a salt thereof can be a production intermediate for compound (ZI).

[0109]

[0110] In formula (im-1a), Q １ is the same as defined in the compound of formula (Z-I). １ is preferably a substituted phenyl group. The substituent on the phenyl group is preferably a halogeno group, a C1-6 alkyl group or a C1-6 haloalkyl group, more preferably a C1-6 haloalkyl group. １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group. The substituent on the "C2-6 alkyl group" and the "C3-6 cycloalkyl group" is preferably a halogeno group. Among these, R １ａ is preferably an unsubstituted C2-6 alkyl group, more preferably a t-butyl group. １ａ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group. １ａ is preferably a carboxyl group or a C1-6 alkoxycarbonyl group.

[0111] A compound represented by the following formula (f-1) (hereinafter may be referred to as compound (f-1)) or a compound represented by the following formula (f-2) (hereinafter may be referred to as compound (f-2)) can be a production intermediate for compound (Z-I).

[0112]

[0113] Production Intermediates The compound represented by the following formula (im-2) or a salt thereof can be a production intermediate for compound (ZI).

[0114]

[0115] In formula (im-2), Q １ is the same as defined in the compound of formula (Z-I). １ is preferably a substituted or unsubstituted phenyl group. The substituent on the "phenyl group" is preferably a halogeno group, a C1-6 alkyl group, or a C1-6 haloalkyl group, more preferably a halogeno group or a C1-6 haloalkyl group, and even more preferably a C1-6 haloalkyl group. R １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group. The substituent on the "C2-6 alkyl group" and the "C3-6 cycloalkyl group" is preferably a halogeno group. Among these, R １ａ is preferably an unsubstituted C2-6 alkyl group, more preferably a t-butyl group.

[0116] As shown in Scheme 1, the compound of formula (im-1) can be produced by a method including a step of reacting the compound of formula (im-3) with the compound of formula (im-4), and a reaction step of converting the compound of formula (im-2) obtained by the reaction into the compound of formula (im-1).

[0117]

[0118] In the compound of formula (im-3), G is a halogeno group, and R １ａ is a compound having the same definition as in the compound of formula (im-1a). １ is a compound having the same definition as in the compound of formula (im-1a). １ and R １ａ is the same as defined in the compound of formula (im-1a).１ represents a hydroxyl group or a substituted or unsubstituted C1-6 alkoxy group, and Q １ and R １ａ is the same as defined in the compound of formula (im-1a).

[0119] The compound of formula (im-2) can be produced by reacting the compound of formula (im-3) 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 the acid scavenger include common inorganic bases and organic bases. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred, and alkali metal carbonates such as potassium carbonate and cesium carbonate, and tertiary amines such as dimethylglycine are more preferred. The reaction temperature is set appropriately, but is, for example, about 100°C to 200°C. The reaction time is set appropriately, but is, for example, about 0.5 hours to 6 hours.

[0120] U １ The compound of formula (im-1) in which is a hydroxyl group can be produced by hydrolyzing the compound of formula (im-2) under acidic or basic conditions. Examples include a method using trifluoroacetic acid under acidic conditions, and a method using lithium hydroxide under basic conditions in a mixed solvent system of tetrahydrofuran (THF) and water, or a mixed solvent system of an alcohol such as methanol, THF, and water. Among these, the method using basic conditions is preferred. The hydrolysis temperature is appropriately set, but is, for example, about 0°C to 60°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 24 hours.

[0121] Alternatively, when an amide is obtained without hydrolyzing to a carboxylic acid using an aqueous solution of an alkali metal hydroxide such as sodium hydroxide in an alcohol solvent such as ethanol, the carboxylic acid can be obtained by reacting with sodium nitrite and a nitrite ester in an acetic acid solvent. The reaction temperature is appropriately set, but is, for example, about 0°C to 100°C, preferably about 0°C to 10°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 6 hours.

[0122] U １ The compound of formula (im-1) in which is a halogeno group is １ is a hydroxyl group, with a halogenating reagent. The compound of formula (im-3) may be commercially available or may be prepared by a known method.

[0123] Production Intermediates The compound represented by the following formula (im-1aS) or a salt thereof can be a production intermediate for compound (ZI).

[0124]

[0125] In the formula (im-1aS), Q １ is the same as defined in the compound of formula (Z-I). １ is preferably a substituted phenyl group. The substituent on the phenyl group is preferably a halogeno group, a C1-6 alkyl group or a C1-6 haloalkyl group, more preferably a C1-6 haloalkyl group. １ is the same as defined in the compound of formula (Z-I). １ is preferably an unsubstituted C1-6 alkyl group, more preferably a t-butyl group. １ａ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group. １ａ is preferably a carboxyl group or a C1-6 alkoxycarbonyl group.

[0126] Production Intermediates The compound represented by the following formula (im-2S) or a salt thereof can be a production intermediate for compound (ZI).

[0127]

[0128] In the formula (im-2S), Q １ is the same as defined in the compound of formula (Z-I). １is preferably a substituted or unsubstituted phenyl group. The substituent on the "phenyl group" is preferably a halogeno group, a C1-6 alkyl group, or a C1-6 haloalkyl group, more preferably a halogeno group or a C1-6 haloalkyl group, and even more preferably a C1-6 haloalkyl group. R １ is the same as defined in the compound of formula (Z-I). １ is preferably an unsubstituted C1-6 alkyl group, more preferably a t-butyl group.

[0129] As shown in Scheme 2, the compound of formula (im-1S) can be produced by a method including a step of reacting the compound of formula (im-3′) with the compound of formula (im-4S), and a reaction step of converting the compound of formula (im-2S) obtained by the reaction into the compound of formula (im-1S).

[0130]

[0131] In the compound of formula (im-3′), G is a halogeno group, and R １ is a compound having the same definition as in the compound of formula (im-1aS). １ is a compound having the same definition as in the compound of formula (im-1aS). １ and R １ is the same as defined in the compound of formula (im-1aS). The compound of formula (im-1S) is a compound of formula (im-1aS) １ represents a hydroxyl group or a halogeno group, and Q １ and R １ is the same as defined in the compound of formula (im-1aS).

[0132] The compound of formula (im-2S) can be produced by reacting the compound of formula (im-3') with the compound of formula (im-4S) by a well-known method. The reaction may be carried out in the presence of an acid scavenger. Examples of the acid scavenger include common inorganic bases and organic bases. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic amines are preferred, and alkali metal carbonates such as potassium carbonate and cesium carbonate, and tertiary amines such as dimethylglycine are more preferred. The reaction temperature is set appropriately, but is, for example, about 100°C to 200°C. The reaction time is set appropriately, but is, for example, about 0.5 hours to 6 hours.

[0133] U １ The compound of formula (im-1S), in which is a hydroxyl group, can be produced by hydrolyzing the compound of formula (im-2S) under acidic or basic conditions. Examples include a method using trifluoroacetic acid under acidic conditions, and a method using lithium hydroxide under basic conditions in a mixed solvent system of tetrahydrofuran (THF) and water, or a mixed solvent system of an alcohol such as methanol, THF, and water. Among these, the method using basic conditions is preferred. The hydrolysis temperature is appropriately set, but is, for example, about 0°C to 60°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 24 hours.

[0134] Alternatively, when an amide is obtained without hydrolyzing to a carboxylic acid using an aqueous solution of an alkali metal hydroxide such as sodium hydroxide in an alcohol solvent such as ethanol, the carboxylic acid can be obtained by reacting with sodium nitrite and a nitrite ester in an acetic acid solvent. The reaction temperature is appropriately set, but is, for example, about 0°C to 100°C, preferably about 0°C to 10°C. The hydrolysis time is appropriately set, but is, for example, about 1 hour to 6 hours.

[0135] U １ The compound of formula (im-1S) in which is a halogeno group is １is a hydroxyl group, with a halogenating reagent. The compound of formula (im-3') may be commercially available or may be prepared by a known method.

[0136] The agricultural and horticultural fungicide of this embodiment can be used to control plant diseases caused by a wide variety of filamentous fungi, for example, fungi belonging to the phylum Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and Zygomycetes.

[0137] Examples of plant diseases (pathogens) that can be controlled are shown below. Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thanatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomyces cochlioides, Pythium Groundnut: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum, Alternaria alternata, Sclerotium rolfsii, Mycosphaerella berkeleyi, Calonectria ilicicola) etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine splitting (Fusarium oxysporum), sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), seedling damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial spot (Pseudomonas syringae pv. Lachrymans), etc. Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), hemi-wilt (Verticillium albo-atrum, Verticilliumdahliae), powdery mildew (Oidium neolycopersici), ring blight (Alternaria solani), sooty mold (Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), sclerotinia sclerotiorum, etc. Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), sooty mold (Mycovellosiella nattrassii), sclerotinia sclerotiorum, verticillium wilt (Verticillium dahliae), brown spot (Phomopsis vexans), etc. Pepper: late blight (Phytophthora capsici), gray mold (Botrytis cinerea), sclerotinia sclerotiorum), anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc. Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopus stolonifer), chlorosis (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia sclerotiorum, etc. Onion: Gray rot (Botrytis allii), gray mold (Botrytis cinerea), white spot leaf blight (Botrytis squamosa), Peronospora destructor, white late blight (Phytophthora porri), Ciborinia allii, BotrytisOnions: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black sclerotial rot (Sclerotium cepivorum), rust (Puccinia allii), white leaf blight (Botrytis squamosa), southern blight (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Leeks: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black sclerotial rot (Sclerotium cepivorum), rust (Puccinia allii), white leaf blight (Botrytis squamosa), southern blight (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Cabbages: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinia rot (Sclerotinia sclerotiorum), black mold (Alternaria brassicicola), gray mold (Botrytis cinerea), root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), white rust (Albugo macrospora), etc. Lettuces: rot (Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), Mirafiori lettuce big-vein ophiovirus, root rot (Fusarium oxysporum), basal rot (Rhizoctoniasolani), powdery mildew (Golovinomyces orontii), etc. Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular spot (Phaeoisariopsis griseola), etc. Peas: Brown spot (Mycosphaerella blight), gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, powdery mildew (Erysiphe pisi), etc.

[0138] Apple: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), monilinia (Monilinia mali), black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), red spot (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), fire blight (Erwinia amylovora), silver leaf (Chondrostereum) Plum: Black spot (Cladosporium carpophilum), Gray mold (Botrytis cinerea), Brown rot (Monilinia mumecola), Sooty spot (Peltaster sp.), Fruit blister (Taphrina pruni), Brown hole (Phloeosporella padi), Persimmon: Powdery mildew (Phyllactinia kakicola), Anthracnose (Gloeosporium kaki), Angular leaf spot (Cercospora kaki), Round leaf spot (Mycosphaerella nawae), Gray mold (Botrytis cinerea), Sooty spot (Zygophiala jamaicensis), Peach: Brown rot (Monilinia fructicola, Monilinia fructigena), black spot (Cladosporiumcarpophilum), Phomopsis rot (Phomopsis sp.), bacterial perforation (Xanthomonas campestris pv.Plum: leaf curl (Taphrina pruni), leaf blister (Taphrina deformans), anthracnose (Colletotrichum gloeosporioides), brown shot hole (Phloeosporella padi), wood ear (Coriolus versicolor), etc. Almond: gray mold (Monilinia laxa), blotch (Stigmina carpophila), black spot (Cladosporium carpophilum), leaf swelling (Polystigma rubrum), blotch and defoliation (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Peach: gray mold (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Young fruit sclerotinia (Monilinia kusanoi), Brown hole (Mycosphaerella cerasella), Powdery mildew (Podosphaera tridactyla), etc. Grapes: Gray mold (Botrytis cinerea), Powdery mildew (Uncinula necator), Late rot (Glomerella cingulata, Colletotrichum acutatum), Downy mildew (Plasmopara viticola), Black rot (Elsinoe ampelina), Brown spot (Pseudocercospora vitis), Black rot (Guignardia bidwellii), White rot (Coniella castaneicola), Rust (Phakopsora ampelopsidis), White cotton snow (causative agent unidentified), Crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: Black spot (Venturia nashicola), Red spot (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukushii), brown spot (Stempphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: ring spot (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red burn (Pseudomonas syringae), blight (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), canker disease (Xanthomonas campestris pv.Citri), powdery mildew (Oidiumsp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: blossom rot bacterial disease (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytiscinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty spot (Pseudocercospora actinidiae), etc. Olive: anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), peacock spot (Spilocaea oleaginea), etc. Chestnut: anthracnose (Colletotrichum gloeosporioides), etc.

[0139] Wheat: powdery mildew (Blumeria graminis f.sp. tritici), scab (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), brown rust (Puccinia recondita), stripe 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), scald (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 (Cochliobolusmiyabeanus), seedling damping-off (Pythium graminicola), white leaf blight (Xanthomonas oryzae), bacterial seedling damping-off (Burkholderia plantarii), brown stripe (Acidovorax avenae), bacterial grain rot (Burkholderia glumae), leaf streak (Cercospora oryzae), rice smut (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black-bellied rice (Alternaria padwickii), pink rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), late blight (Phytophthora nicotianae), etc. Tulip: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. 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 damping-off (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), damping-off (Rhizoctonia solani), Fusarium damping-off (Fusarium solani), etc. Gerberas: gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lily: Leaf blight (Botrytis elliptica, Pestalotiopsissp.), Gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), 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.), Blight (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc. Orchardgrass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purple spot (Cercospora kikuchii), Downy mildew (Peronospora manshurica), Stem rot (Phytophthora sojae), Rust (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Anthracnose (Colletotrichum truncatum), Gray mold (Botrytis cinerea), Black rot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potato: Late blight (Phytophthora infestans), Summer blight (Alternaria solani), Black spot (Thanatephorus cucumeris), Verticillium wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), Black leg (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), common scab (Streptomycesspp.), Sclerotinia sclerotiorum, etc. Yam: Leaf blight (Cylindrosporium dioscoreae), Anthracnose (Colletotrichum gloeosporioides), Blue mold (Penicillium sclerotigenum), etc. Sweet potato: Purple root rot (Helicobasidium mompa), Fusarium oxysporum, etc. Taro: Late blight (Phytophthora colocasiae), Stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythium myriotylum), White spot (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), canker (Xanthomonas 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 melanocephala) etc. Corn: Hail leaf spot (Gloeocercospora sorghi), rust (Pucciniasorghi), southern rust (Puccinia polysora), ear smut (Ustilago maydis), southern leaf blight (Cochliobolus heterostrophus), sooty blight (Setosphaeria turcica), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: damping off (Pythium sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0140] The agricultural and horticultural fungicide of this embodiment is preferably used on plants such as grains; vegetables; root vegetables; potatoes; fruit trees, trees such as tea, coffee, and cacao; pasture grasses; turf; and cotton.

[0141] The agricultural and horticultural fungicide of this embodiment can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. Furthermore, improved varieties and varieties, cultivated varieties, mutants, hybrids, and genetically modified organisms (GMOs) of these plants can also be targeted.

[0142] The agricultural and horticultural fungicide of this embodiment can be used for seed treatment, foliage spray, soil application, water surface application, etc., which are carried out to control various diseases that occur in agricultural and horticultural crops including flowers, turf, and pasture grass.

[0143] The agricultural and horticultural fungicide of this embodiment may contain other components besides the active ingredient (Z-I). Examples of other components include known carriers used for formulation. Examples of other components include conventionally known fungicides, insecticides / miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed, etc. (hereinafter, sometimes referred to as the active ingredient (II)). The agricultural and horticultural fungicide of this embodiment may exhibit a synergistic effect by containing the active ingredient (Z-I) and the active ingredient (II).

[0144] Specific examples of fungicides as the active ingredient (II) that can be mixed or used in combination with the agricultural and horticultural fungicide of this embodiment are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, ofrace; (b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol; (c) DNA / RNA synthesis inhibitors: hymexazole, octhilinone; (d) DNA topoisomerase II inhibitors: oxolinic acid; (e) DHODH inhibitors: ipflufenoquin, quinofumelin

[0145] (2) Mitotic and cytostatic agents: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, diethofencarb, zoxamide, ethaboxam; (b) cytostatic agents: pencycuron; (c) spectrin-like protein delocalization inhibitors: fluopicolide, fluopimomide; (d) actin / myosin / fimbrin function: fenamacryl, metrafenone, pyriophenone; (e) tubulin dynamics modulators: pyridaclomethyl;

[0146] (3) Respiratory inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad, fenazaquin; (b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenfuram, flumecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pydiflumetofen, isoflucipram, pyraziflumide, inpirfluxam; (c) Complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, cumoxystrobin, methoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, methyltetraprole, mandestrobin; (d) Complex III-ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom, fenpicoxamide, florylpicoxamide; (e) oxidative phosphorylation uncouplers: binapacryl, meptyldinocap, dinocap, fluazinam; (f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide; (g) ATP production inhibitors: silthiofam; (h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctradine;

[0147] (4) Amino acid and protein synthesis inhibitors: (a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; (b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline; (c) leucyl-tRNA synthetase inhibitors: tavaborole;

[0148] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxyfen, proquinazid; (b) MAP / histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil, chlozolinate, dimethaclon, iprodione, procymidone, vinclozolin;

[0149] (6) Lipid and cell membrane synthesis inhibitors: (a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; (b) lipid peroxidizing agents: biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl, etridiazole; (c) agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb; (d) agents disrupting cell membranes: extracts of Gosei-kajuput (tea tree); (e) agents specifically binding to ergosterol: natamycin;

[0150] (7) Cell membrane sterol biosynthesis inhibitors: (a) C14 demethylation inhibitors in sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, biniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; (c) Inhibitors of 3-ketoreductase in C4 demethylation in the sterol biosynthesis system: fenhexamid, fenpyrazamine; (d) Inhibitors of squalene epoxidase in the sterol biosynthesis system: pyributicarb, naftifine, terbinafine;

[0151] (8) Cell wall synthesis inhibitors: (a) chitin synthase inhibitors: polyoxin, polyoxolim; (b) cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthiavalicarb isopropyl, iprovalicarb, valifenalate, mandipropamide;

[0152] (9) Melanin biosynthesis inhibitors: (a) Reductase inhibitors of melanin biosynthesis: fthalide, pyroquilon, tricyclazole; (b) Dehydratase inhibitors of melanin biosynthesis: carpropamid, diclocymet, fenoxanil; (c) Polyketide synthesis inhibitors of melanin biosynthesis: tolprocarb;

[0153] (10) Resistance inducers of host plants: (a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl, probenazole, tiadinil, isotianil, diclobenthiazox; (b) Others: ipfentrifluconazole, laminarin, giant knotweed extract; fosetyl aluminum, fosetyl calcium, fosetyl sodium, phosphoric acid, phosphate, phosphorous acid, phosphite;

[0154] (11) Agents of unknown activity: cymoxanil, tecloftalam, triazoxide, flusulfamide, diclomedine, cyflufenamid, dodine, dodine free base, fluthianil, ferimzone, tebufloquine, picarbutrazox, validamycin;

[0155] (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, ferbam, mancozeb, maneb, mancopper, metiram, metiram zinc, polycarbamate, propineb, thiram, zineb, ziram; captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine tribesylate, anilazine, dithianone, chinomethionate, fluorimide, metasulfocarb;

[0156] (13) Other agents: DBEDC, Fluorofolpet, Bis(8-quinolinolato)copper(II), Propamidine, Chloropicrin, Cyprofuram, Agrobacterium, Bethoxadin, Diphenylamine, Methylisothiocyanate (MITC), Mildeomycin, Capsaicin, Kufuraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Difenzoquat, Difenzoquat Methylsulfonate, Flumetober, Irmamycin, Nitrotarisopropyl, Oxamocarb, Pyrrolnitrin, Tolnifanide, Zaliramide, Argophase, Amicarthiazole, Oxathiapiproline, Fluoxapiproline, Benthiazole, Trichlamide, Uniconazole, Oxfenthiin, Pyrapropoin, Fluindapyr, Aminopyrifen, Dipimethitron, Flufenoxadiazam, Flumethylsulfolim, Feneptamidoquin;

[0157] (14) Biological preparations having 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 asperellum T34 strain, Trichoderma asperellum kd strain; Trichoderma harzianum T-22 strain; ... Derma virens strain G-41; Clonostachys rosea strain J1146, Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON / M / 91-08; Hanseniaspora ubaraum strain BC18Y; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisiae strain LAS02, Saccharomyces cerevisiae strain DDSF623; Bacillus amyloliquefaciens Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332; Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus Bacillus subtilis strain HAI-0404, Bacillus subtilis strain RTI477; Bacillus veresensis strain RTI301; PHC25279; Gluconobacter selinus strain BC18B; Pseudomonas chlororaphis strain ASF009; Pseudomonas rhodesiae strain HAI-0804; Streptomyces griseoviridis strain K61, and Streptomyces ridicus strain WYEC108.

[0158] Specific examples of insecticides / acaricides, nematicides, soil pesticides, anthelmintics, etc. as the active ingredient (II) that can be mixed or used in combination with the agricultural and horticultural fungicide of this embodiment are shown below.

[0159] (1) Acetylcholinesterase (AChE) inhibitors (a) Carbamate acetylcholinesterase (AChE) inhibitors: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb; fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb;(b) organophosphorus acetylcholinesterase (AChE) inhibitors: acephate, azamethiphos, azinphos ethyl, azinphos methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos methyl, coumaphos, cyanophos, demeton -S- methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fanflu, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isocarbophos, isopropyl = O- (methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion, para Thionemethyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, fonofos, formothion, fosmetilan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos;

[0160] (2) GABA-gated chloride ion (chloride ion) channel blockers: chlordane, endosulfan, ethiprole, fipronil; acetoprole, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor, flufifrol;

[0161] (3) Sodium channel modulators (a) Pyrethroid sodium channel modulators: acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, 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, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, fenothrin phosphorus [(1R)-trans isomer], prallethrin, pyrethrum, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, telallethrin, κ-bifenthrin, chloroprallethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioethanomethrin; (b) Sodium channel modulators (DDTs): DDT, methoxychlor;

[0162] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradifurone, dichloromezothiazol, phenmezodithiazol, triflumezopyrim, flupirim; (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: spinetoram, spinosad; (6) Glutamate-activated 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;

[0163] (7) Juvenile hormone analogues: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen; diofenolan, epofenonane, triprene; (8) Other non-specific (multi-site) inhibitors: 1,3-dichloropropene, methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metam potassium salt, metam sodium salt; (9) Chordotonal organ TRPV channel modulators: pymetrozine, pyrifluquinazone, afidopiropen; (10) Mites growth inhibitors: clofentezine, diflobidazine, hexythiazox, etoxazole; (11) Microorganism-derived insect midgut membrane disruptors: Bacillus thuringiensis subsp. israerensi, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Proteins found in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus;

[0164] (12) Mitochondrial ATP synthase inhibitors: diafenthiuron, azocyclotine, cyhexatin, fenbutatin oxide, propargite, tetradifon; (13) oxidative phosphorylation uncouplers that disrupt the proton gradient: chlorfenapyr, DNOC, sulfuramide; binapacryl, dinobuton, dinocap; (14) nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt; nereistoxin; (15) chitin biosynthesis inhibitors, type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron; buprofezin, fluazuron; (16) chitin biosynthesis inhibitors, type 1: (17) Molting inhibitors: cyromazine; (18) Molting hormone (ecdysone) receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide;

[0165] (19) Octopamine receptor agonists: amitraz; demiditraz, chlordimeform; (20) Mitochondrial electron transport chain complex III inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate; (21) Mitochondrial electron transport chain complex I inhibitors (METI): fenazaquin, fenpiroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; (22) Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone; (23) Acetyl CoA carboxylase inhibitors: spidoxamato, spirodiclofen, spiromesifen, spiropydione, spirotetramat; (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, piflubumid;

[0166] (26) Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetraniliprole; tetrachlorantraniliprole; (27) chordotonal organ modulators of unspecified target sites: flonicamide; (28) GABA-gated chloride ion (chloride ion) channel allosteric modulators: fluxametamide, isocycloceram, brofuranilide; afoxolaner, fluralaner, lotineral, sarolaner; (29) other insecticides, acaricides: acinonapyr, flometoquin, ledoprona, dinpropylidaz, oxazosulfil, azadirachtin, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, dicofol, lime sulfur mixture, mancozeb, pyridalyl, sulfur; Cryolite, benclothiaz, amidoflumet, DCIP, phenisobromorate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossiplura, japonirua, methoxadiazone, petroleum oil, potassium oleate, tetrasulfur, triarane, afidopiropen, flufiprole, fluensulfo n, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, broflanilide, Steinernema carpocapsae, Steinernema glacerai, Pasteuria penetrans, Pecilomyces tenuipes, Pecilomyces fumosoroseus, Beauveria bassiana, Beauveria brongniartii, Metarhizium anisopliae, Verticillium lecanii, fluhexafon, cyclopyrazoflor;

[0167] (30) Anthelmintics: (a) benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambandazole; (b) salicylanilides: closantel, oxyclozanide, lafoxanide, niclosamide; (c) substituted phenols: nitroxynil, nitroscanate; (d) pyrimidines: pyrantel, morantel; (e) imidazothiazoles: levamisole, tetramisole; (f) tetrahydropyrimidines: praziquantel, epsiprantel; (g) other anthelmintics: Cyclodien, riania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, arsenamide.

[0168] Specific examples of plant regulators as the active ingredient (II) that can be mixed or used in combination with the agricultural and horticultural fungicide 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 aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiazolinone ... ol, 1-naphthylacetamide, ethychlozate, cloxifonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, daminozide.

[0169] {Formulation} The agricultural and horticultural fungicide of this embodiment is not particularly limited by its formulation. For example, it may be in the form of a wettable powder, emulsifiable concentrate, dust, granule, water-soluble powder, suspension, water-dispersible granule, tablet, etc. The method for preparing the formulation is not particularly limited, and a known preparation method can be used depending on the formulation.

[0170] Some formulation examples are shown below. The formulations shown below are merely examples and can be modified within the scope of the present invention. The present invention is not limited in any way by the formulation examples below, and the triazole compound of the present invention may be used as it is as an agricultural and horticultural fungicide. "Parts" means "parts by mass" unless otherwise specified.

[0171] (Formulation Example 1: Wettable Powder) 40 parts of the triazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and then finely pulverized to obtain a wettable powder containing 40% by mass of the active ingredient.

[0172] Formulation Example 2: Emulsifiable concentrate 30 parts of the triazole 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 emulsifiable concentrate containing 30% by mass of the active ingredient.

[0173] Formulation Example 3: Granules 5 parts of the triazole compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, then finely pulverized, and then granulated to particle diameters of 0.5 to 1.0 mm to obtain granules containing 5% by mass of the active ingredient.

[0174] Formulation Example 4: Granules 5 parts of the triazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are uniformly mixed and pulverized, and then water is added thereto and kneaded. Thereafter, the mixture is granulated and dried to obtain granules containing 5% by mass of the active ingredient.

[0175] Formulation Example 5: Suspension 10 parts of the triazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of a sodium salt of polycarboxylic acid, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized to a particle size of 3 microns or less to obtain a suspension containing 10% by mass of the active ingredient.

[0176] (Formulation Example 6: Water Dispersible Granules) 40 parts of the triazole compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate, and 5 parts of a formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed and finely pulverized. An appropriate amount of water is then added thereto, and the mixture is kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a water dispersible granule containing 40% by mass of the active ingredient.

[0177] Next, the present invention will be explained in more detail by showing compound production examples, but the present invention is not limited to the following examples in any way.

[0178] [Production Example 1] N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-methyl-4-(m-tolyloxy)-1H-1,2,3-triazole-5-carboxamide (Compound Number: 1) was produced by the following steps. Step 1: Conversion to 4-bromo-N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-methyl-1H-1,2,3-triazole-5-carboxamide

[0179]

[0180] 4-Bromo-1-methyl-1H-1,2,3-triazole-5-carboxylic acid (0.10 g) was dissolved in dichloromethane (3 mL). 2-(2,4-dimethylphenyl)-2,2-difluoroethan-1-amine hydrochloride (0.12 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.14 g), 1-hydroxybenzotriazole monohydrate (0.008 g), and triethylamine (0.12 g) were added. The mixture was stirred for 16 hours. The reaction mixture was then concentrated using an evaporator. The residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.12 g of 4-bromo-N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-methyl-1H-1,2,3-triazole-5-carboxamide (64% yield).

[0181] Step 2: Conversion to N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-methyl-4-(m-tolyloxy)-1H-1,2,3-triazole-5-carboxamide

[0182]

[0183] 4-Bromo-N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-methyl-1H-1,2,3-triazole-5-carboxamide (0.03 g) was added to 3-methylphenol (0.017 g), cesium carbonate (0.078 g), copper iodide (0.003 g), and dimethylglycine (0.0016 g). The mixture was stirred at 130°C for 5 hours. The mixture was then purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.002 g (6% yield) of N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-methyl-4-(m-tolyloxy)-1H-1,2,3-triazole-5-carboxamide.

[0184] Production Example 2 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxamide (Compound Number: 2) was produced by the following steps. Step 1: Conversion to 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxamide

[0185]

[0186] 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid (0.060 g) was dissolved in tetrahydrofuran (0.39 mL). 2-(2,4-dimethylphenyl)ethan-1-amine (21 mg), triethylamine (36 mg), and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (68 mg) were added and stirred at 25°C for 18 hours. The reaction mixture was purified by preparative chromatography and then by silica gel column chromatography to obtain 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxamide (0.053 g, yield 97%).

[0187] Production Example 3 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid (compound number f-3) was produced by the following steps.

[0188] Step 1: Conversion to 4,5-dibromo-1-(tert-butyl)-1H-1,2,3-triazole

[0189]

[0190] 4,5-Dibromo-1H-1,2,3-triazole (3.4 g), tert-butanol (2.2 g), and p-toluenesulfonic acid monohydrate (0.57 g) were added to toluene (50 mL) and stirred for 3 hours at 70° C. After the solvent was distilled off, the residue was purified by silica gel column chromatography to obtain 4,5-dibromo-1-(tert-butyl)-1H-1,2,3-triazole (1.8 g).

[0191] Step 2: Conversion to 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid

[0192]

[0193] 4,5-Dibromo-1-(tert-butyl)-1H-1,2,3-triazole (1.7 g) was dissolved in tetrahydrofuran (15 mL) at 0 °C, and isopropylmagnesium chloride-lithium chloride complex (1.4 g) was added and stirred for 2 hours. Carbon dioxide (10 g) was then bubbled through. The reaction was quenched with 1 M HCl, extracted with ethyl acetate, and the solvent was evaporated to give 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (1.5 g).

[0194] Step 3: Conversion to isopropyl 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate

[0195]

[0196] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (1.5 g), isopropyl iodide (3.1 g), and potassium carbonate (2.5 g) were added to N,N-dimethylformamide (20 mL) and stirred at 45°C for 3 hours. Water was added, and the mixture was extracted with ethyl acetate. The solvent was evaporated. Purification by silica gel column chromatography afforded isopropyl 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate (1.4 g, 80% yield).

[0197] Step 4: Conversion to isopropyl 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate

[0198]

[0199] To toluene (2.5 mL) were added α,α,α-trifluoro-m-cresol (0.32 g), isopropyl 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate (0.29 g), N,N-dimethylglycine (21 mg), and copper iodide (19 mg). The mixture was microwaved at 150 °C for 1.5 hours. Purification by silica gel column chromatography afforded 0.20 g of isopropyl 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate.

[0200] Step 5: Conversion to 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid

[0201]

[0202] Isopropyl 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylate (0.20 g) was dissolved in tetrahydrofuran (0.50 mL), water (0.17 mL), and methanol (0.50 mL). Lithium hydroxide monohydrate (73 mg) was added and the mixture was stirred at 25°C for 16 hours. The reaction was quenched with 1N hydrochloric acid, and the mixture was separated with ethyl acetate and dried over magnesium sulfate. The solvent was evaporated to give 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-1,2,3-triazole-5-carboxylic acid (0.12 g).

[0203] Production Example 4 1-(tert-butyl)-4-(3-chlorophenoxy)-N-(4-methylphenethyl)-1H-1,2,3-triazole-5-carboxamide (Compound Number: 10) was produced by the following steps.

[0204] Step 1: Conversion to 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide

[0205]

[0206] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (0.50 g) was dissolved in N,N-dimethylformamide (6.7 mL). Ammonium chloride (0.21 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (1.1 g), and triethylamine (0.61 g) were added. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator and purified by silica gel column chromatography to give 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide (0.36 g, 73% yield).

[0207] Step 2: Conversion to 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile

[0208]

[0209] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide (0.050 g) was dissolved in dichloromethane (0.67 mL). Trifluoroacetic anhydride (0.13 g) and triethylamine (72 mg) were added, and the mixture was stirred at 25°C for 1 hour. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator. The residue was separated by silica gel column chromatography and purified by amino silica gel column chromatography to give 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.039 g, 84% yield).

[0210] Step 3: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonitrile

[0211]

[0212] 1-Chloro-3-hydroxybenzene (73 mg), 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.10 g), and potassium carbonate (90 mg) were added to dimethyl sulfoxide (2.2 mL) and stirred at 120°C for 4 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator. Purification by silica gel chromatography afforded 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonitrile (0.09 g, 70% yield).

[0213] Step 4: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxamide

[0214]

[0215] 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carbonitrile (0.15 g) and sodium hydroxide (4 M, 2.7 mL) were added to ethanol (2.7 mL) and stirred at 100°C for 12 hours. The reaction mixture was quenched with 1N hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate. The solvent was removed using an evaporator to give 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxamide (0.16 g).

[0216] Step 5: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxylic acid

[0217]

[0218] 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxamide (0.16 g) and sodium nitrite (0.11 g) were added to trifluoroacetic acid (1.8 mL) at 0°C and stirred at 0°C for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate. The solvent was removed using an evaporator to give 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxylic acid (0.13 g, 81% yield).

[0219] Step 6: Conversion to 1-(tert-butyl)-4-(3-chlorophenoxy)-N-(4-methylphenethyl)-1H-1,2,3-triazole-5-carboxamide

[0220]

[0221] 1-(tert-butyl)-4-(3-chlorophenoxy)-1H-1,2,3-triazole-5-carboxylic acid (41 mg), 2-(4-methylphenyl)ethan-1-amine (23 mg), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (80 mg), and triethylamine (42 mg) were added to tetrahydrofuran (0.70 mL) and stirred at 25°C for 16 hours. The reaction mixture was purified by preparative high-performance liquid chromatography (eluent: acetonitrile / water) to give 1-(tert-butyl)-4-(3-chlorophenoxy)-N-(4-methylphenethyl)-1H-1,2,3-triazole-5-carboxamide (0.055 g, 0.13 mmol, 95%).

[0222] [Production Example 5] 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(2,4-dimethylphenethyl)-1H-1,2,3-triazole-5-carboxamide (Compound Number: 67) was produced in the following steps. Step 1: Conversion to 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile

[0223]

[0224] 4-Bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (1.5 g) was dissolved in 1-methyl-2-pyrrolidone (22 mL). Benzyl alcohol (4.3 g) and cesium carbonate (10.7 g) were added at room temperature and stirred at 125°C for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to give 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.15 g, 9% yield).

[0225] Step 2: Conversion to 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide

[0226]

[0227] 4-(Benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.15 g) was dissolved in ethanol (3.1 mL). Sodium hydroxide (0.25 g) was added and the mixture was heated to reflux for 1 hour. 1N hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide (0.17 g, 99% yield).

[0228] Step 3: Conversion to 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid

[0229]

[0230] 4-(Benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxamide (0.15 g) was dissolved in trifluoroacetic acid (1.1 mL). Sodium nitrite (0.11 g) was added at 0°C, and the mixture was stirred at 0°C for 1 hour. The reaction mixture was quenched with water and then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator to give 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (0.12 g, 80% yield).

[0231] Step 4: Conversion to isopropyl 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate

[0232]

[0233] 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylic acid (0.12 g), isopropyl iodide (0.19 g), and cesium carbonate (0.36 g) were added to N,N-dimethylformamide (1.7 mL) and stirred at 35°C for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to give isopropyl 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate (0.12 g, 69%).

[0234] Step 5: Conversion to isopropyl 1-(tert-butyl)-4-hydroxy-1H-1,2,3-triazole-5-carboxylate

[0235]

[0236] Isopropyl 4-(benzyloxy)-1-(tert-butyl)-1H-1,2,3-triazole-5-carboxylate (0.12 g) was dissolved in tetrahydrofuran (1.7 mL). 10% palladium on activated carbon (0.04 g) was added at room temperature and stirred under a hydrogen atmosphere for 18 hours. The reaction mixture was filtered through Celite, and the solvent was evaporated under reduced pressure to give isopropyl 1-(tert-butyl)-4-hydroxy-1H-1,2,3-triazole-5-carboxylate (0.05 g, 58%).

[0237] Step 6: Conversion to isopropyl 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-1,2,3-triazole-5-carboxylate

[0238]

[0239] Isopropyl 1-(tert-butyl)-4-hydroxy-1H-1,2,3-triazole-5-carboxylate (0.04 g) was dissolved in N,N-dimethylformamide (1.8 mL). 6-Chloro-2-fluoropyridine (0.19 g) and potassium carbonate (0.19 g) were added at room temperature and stirred at 120 °C for 2 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate) to yield isopropyl 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-1,2,3-triazole-5-carboxylate (0.035 g, 50%).

[0240] Step 7: Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-1,2,3-triazole-5-carboxylic acid

[0241]

[0242] Isopropyl 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-1,2,3-triazole-5-carboxylate (0.035 g) was dissolved in tetrahydrofuran (1.2 mL), methanol (0.4 mL), and water (0.4 mL). Lithium hydroxide monohydrate (0.043 g) was added at room temperature, and the mixture was stirred at room temperature for 18 hours. 1N hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with saturated brine. The mixture was then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-1,2,3-triazole-5-carboxylic acid (0.03 g, yield 98%).

[0243] Step 8: Conversion to 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(2,4-dimethylphenethyl)-1H-1,2,3-triazole-5-carboxamide

[0244]

[0245] To dichloromethane (0.70 mL), 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-1H-1,2,3-triazole-5-carboxylic acid (0.008 g), 2-(2,4-dimethylphenyl)ethan-1-amine (0.008 g), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (0.026 g), and triethylamine (0.014 mL) were added and stirred at 25° C. for 16 hours. The reaction solution was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 1-(tert-butyl)-4-((6-chloropyridin-2-yl)oxy)-N-(2,4-dimethylphenethyl)-1H-1,2,3-triazole-5-carboxamide (0.0068 g, 47%).

[0246] [Production Example 6] 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carboxamide (compound number: 89) was produced in the following steps. Step 1: Conversion to 1-(tert-butyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carbonitrile

[0247]

[0248] 2-Naphthol (1.50 g), 4-bromo-1-(tert-butyl)-1H-1,2,3-triazole-5-carbonitrile (0.80 g), and tripotassium phosphate (3.0 g) were added to dimethyl sulfoxide (7.0 mL) and stirred at 110°C for 1 hour. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was concentrated using an evaporator. Purification by silica gel chromatography afforded 1-(tert-butyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carbonitrile (0.53 g, 52% yield).

[0249] Step 2: Conversion to 1-(tert-butyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carboxylic acid

[0250]

[0251] 1-(tert-butyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carbonitrile (0.39 g) and sodium hydroxide (4 M, 6.7 mL) were added to ethylene glycol (13.0 mL) and stirred at 130°C for 13 hours. The reaction mixture was quenched with 1N hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate. The solvent was removed using an evaporator to give 1-(tert-butyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carboxylic acid (0.40 g, yield 73%, purity 76%).

[0252] Step 3: Conversion to 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carboxamide

[0253]

[0254] To dichloromethane (2.6 mL), 1-(tert-butyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carboxylic acid (80 mg), 2-(2,4-dimethylphenyl)ethan-1-amine (58 mg), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) (0.20 g), and triethylamine (78 mg) were added, followed by stirring at 40° C. for 1 hour and then at 25° C. for 16 hours. The reaction mixture was purified by preparative high-performance liquid chromatography (developing solvent: acetonitrile / water) to obtain 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(naphthalen-2-yloxy)-1H-1,2,3-triazole-5-carboxamide (0.050 g, 0.11 mmol, 44%).

[0255] The compounds shown in Table 1 below were produced through the same steps as in the above production examples. The appearances are shown in the properties column. LCMS retention times are also shown.

[0256] LCMS retention times were determined as follows. A system comprised of an ultra-high-performance, high-resolution liquid chromatograph (ACQUITY UPLC H-Class, manufactured by Waters), an HPLC / UHPLC detector (ACQUITY UPLC Photodiode Array (PDA) eλ Detector, manufactured by 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) was equipped with a CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 μm). Measurements were 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 weight of formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). The concentration of the mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then the concentration of the mobile phase (B) was 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 the concentration of the mobile phase (B) was immediately decreased to 30% by mass, and finally the concentration of the mobile phase (B) was maintained at 30% by mass for 0.50 minutes.

[0257] The LCMS (QDa) retention times of compounds 19, 20, 34, 35, 36, and 53 were determined under the following conditions. A system comprised an ultra-high-performance, high-resolution liquid chromatograph (ACQUITY UPLC H-Class, manufactured by Waters), an HPLC / UHPLC detector (ACQUITY UPLC Photodiode Array (PDA) eλ Detector, manufactured by Waters), and a single quadrupole MS detector (LC / MS) (ACQUITY QDa Detector in positive and negative ion electrospray mode) equipped with a CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 μm). The analysis 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% formic acid was used as the mobile phase (A), and acetonitrile was used as the mobile phase (B). The concentration of mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then increased from 30% by mass to 95% by mass over 1.35 minutes at a constant rate, 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.

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292] Preferred triazole compounds of this embodiment are shown in Table 2 below. The appearance is shown in the properties column. Furthermore, the LCMS retention time is also shown.

[0293]

[0294]

[0295]

[0296]

[0297]

[0298] More preferred triazole compounds of this embodiment are shown in Table 3 below. The appearance is shown in the properties column. Furthermore, the LCMS retention time is also shown.

[0299]

[0300]

[0301]

[0302] Compounds that can serve as production intermediates in this embodiment are listed in Table 4 below. The structural formulas of the production intermediates are listed along with their LCMS retention times. The LCMS (QDa) retention time for compound f-25 was determined under the following conditions. A CORTECS UPLC C18 column (Waters, 2.1 x 50 mm, 1.6 μm) was attached to a system comprising an ultra-high-performance, 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)]. The analysis 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 weight of formic acid was used as the mobile phase (A), and acetonitrile was used as the mobile phase (B). The concentration of mobile phase (B) was maintained at 30% by mass for 0.15 minutes, then increased from 30% by mass to 95% by mass over 1.35 minutes at a constant rate, 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.

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313] Compounds that can be used as intermediates in the production of this embodiment are shown in Table 5. The structural formulas of the intermediates are listed along with their LCMS retention times.

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320] Preferred compounds that can be used as production intermediates in this embodiment are shown in Table 6 below. The structural formulas of the production intermediates are also shown along with their LCMS retention times.

[0321]

[0322]

[0323]

[0324] Preferred compounds that can be used as production intermediates in this embodiment are shown in Table 7 below. The structural formulas of the production intermediates are also shown along with their LCMS retention times.

[0325]

[0326]

[0327] More preferred compounds that can be used as production intermediates in this embodiment are shown in Table 8 below. The structural formulas of the production intermediates are listed along with the LCMS retention times.

[0328]

[0329]

[0330] More preferred compounds that can be used as production intermediates in this embodiment are shown in Table 9 below. The structural formulas of the production intermediates are listed along with the LCMS retention times.

[0331]

[0332] The effects of the present invention will be illustrated by the following fungicidal effect test and disease control test.

[0333] (Test of fungicidal effect against gray mold fungus) A spore suspension of gray mold fungus (Botrytis cinerea, Vogel medium) was prepared. The triazole 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 amounts (volume basis) to obtain a test solution with a concentration of the triazole compound of the present invention of 25 ppm by volume. The test solution was dropped into a 96-well microplate (drug-treated group). Equal amounts (volume basis) of dimethyl sulfoxide and the spore suspension were mixed to obtain a control solution. The control solution was dropped into a 96-well microplate (untreated group). These were left to stand at 20°C in a dark place and cultured for 5 days. The 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 incubation) - (OD of drug-treated group before incubation)] / [(OD of untreated group after incubation) - (OD of untreated group before incubation)]}

[0334] A fungicidal effect test against Botrytis cinerea was carried out on Compound Nos. 1 to 5, 7 to 58, 60 to 143, 146 to 152, and 154 to 162. All of the compounds showed a growth inhibition rate of 75% or more.

[0335] (Test of bactericidal effect against grape late rot fungus) The turbidity was measured in the same manner as in the test of bactericidal effect against grape late rot fungus, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Glomerella cingulata (Vogel medium) and the temperature and period of standing were changed to 25°C and 3 days, respectively, and the growth inhibition rate was calculated.

[0336] A fungicidal effect test against grape late rot fungus was carried out on compound numbers 1 to 58, 60 to 143, 146 to 152, and 154 to 162. All compounds showed a growth inhibition rate of 75% or more.

[0337] (Test of fungicidal effect against apple anthracnose fungus) The turbidity was measured and the growth inhibition rate was calculated in the same manner as in the test of fungicidal effect against Botrytis cinerea, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Colletotrichum acutatum (Czapek medium) and the temperature and period of standing were changed to 25°C and 4 days, respectively.

[0338] The fungicidal effect test against apple anthracnose fungus was carried out for compound numbers 1 to 5, 7 to 58, 60 to 143, 146 to 152, and 154 to 162. All of the compounds showed a growth inhibition rate of 75% or more.

[0339] (Test of fungicidal effect against apple brown spot fungus) The turbidity was measured and the growth inhibition rate was calculated in the same manner as in the test of fungicidal effect against Botrytis cinerea, except that the spore suspension of Botrytis cinerea (Vogel medium) was replaced with a spore suspension of Alternaria mali (YBA medium) and the temperature and period of standing were changed to 25°C and 4 days, respectively.

[0340] The fungicidal effect test against Alternaria alternata apple spot was carried out on Compound Nos. 2 to 5, 7 to 37, 39 to 46, 48 to 58, 60 to 67, 69 to 71, 73 to 88, 90 to 92, 94 to 131, 133 to 142, 148 to 152, 154, and 156 to 162. All of the compounds showed a growth inhibition rate of 75% or more.

[0341] (Test for control of cucumber gray mold) 5 parts by mass of the triazole 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 emulsifiable concentrate (1) containing 5% by mass of the active ingredient.

[0342] Water was added to the emulsion (1) to obtain a drug solution containing the triazole compound of the present invention at a concentration of 125 ppm by mass. Subsequently, the drug solution was sprayed onto cucumber seedlings (variety "Jihai" series, cotyledon stage) grown in seedling pots, followed by air drying. Thereafter, a conidial suspension of Botrytis cinerea was dropwise inoculated onto the seedlings (treated group). As a control, a conidial suspension of Botrytis cinerea was dropwise inoculated onto cucumber seedlings not sprayed with the drug solution (untreated group). These were then placed in a moist 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 lesion area ratio using the following formula:

[0343] Control value (%) = 100 - {lesion area rate in treated area / lesion area rate in untreated area} x 100

[0344] Control tests against cucumber gray mold were carried out on compound numbers 2 to 4, 7 to 10, 12 to 23, 25 to 36, 38 to 45, 47 to 67, 69 to 71, 74 to 79, 82 to 88, and 90. The compounds showed a control value of 75% or more.

[0345] (Control test for apple scab) Water was added to the emulsion (1) so that the concentration of the triazole compound of the present invention was 125 ppm by mass, and the triazole compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto apple seedlings (cultivar "Orin", 3-4 leaf stage) grown in nursery pots, followed by air drying. The treated apple seedlings were then inoculated with conidia of the apple scab fungus (Venturia inaequalis) (treated group). As a control, apple seedlings not sprayed with the drug solution were inoculated in the same manner (untreated group). These were then placed in a moist chamber at 20°C, with a 12-hour cycle of light and dark. Twelve to fourteen days after inoculation, the leaves of the apple seedlings were visually observed, and the control value was calculated from the lesion area percentage using the formula used to calculate the control value in the above-mentioned control test for cucumber gray mold.

[0346] Control tests for apple scab were carried out on compound numbers 2 to 4, 7 to 10, 13 to 16, 18, 22, 23, 25, 27, 28, 30 to 37, 40, 42 to 44, 48, 52, 53, 55 to 57, 59, 61, 62, 64, 66, 69, 70, and 74 to 79. The compounds showed a control value of 75% or more.

[0347] (Test for Control of Wheat Powdery Mildew) Water was added to the emulsion (1) so that the concentration of the triazole compound of the present invention was 125 ppm by mass, and the compound was dissolved to obtain a drug solution. Subsequently, the drug solution was sprayed onto wheat seedlings (variety "Chihoku", 1- to 2-leaf stage) grown in seedling pots and air-dried. Subsequently, conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were sprinkled on the seedlings for inoculation (treated group). As a control, conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were sprinkled on wheat seedlings that had not been sprayed with the drug solution (untreated group). These were then placed in a greenhouse at 20°C. Six days after inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated in the same manner as in the previous test.

[0348] A test for controlling wheat powdery mildew was carried out on compound numbers 2 to 4, 7, 8, 10, 12 to 16, 18, 22, 23, 25, 27, 28, 30 to 36, 40, 42 to 44, 47, 48, 51 to 53, 55 to 57, 59, 61 to 64, 66, 67, 69 to 72, 74 to 79, 82 to 88, and 90. The compounds showed a control value of 75% or more.

[0349] In addition to the above tests, the following test can be used to determine the systemicity of a compound: (Systemicity Test for Cucumber Gray Mold) 5 parts by mass of the triazole compound of the present invention, 93.5 parts by mass of N,N-dimethylformamide, and 1.5 parts by mass of polyoxyethylene sorbitan monolaurate are mixed to obtain an emulsifiable concentrate (1) containing 5% by mass of the active ingredient.

[0350] Water was added to the emulsion (1) to obtain a drug solution containing the triazole compound of the present invention at a concentration of 25 mass ppm or 6.3 mass ppm. The drug solution was then sprayed onto the underside of leaves of cucumber seedlings (variety "Jihai", cotyledon stage) grown in seedling pots, and then air-dried and left to stand for 2 days. A conidial suspension of Botrytis cinerea was then dropwise inoculated onto the cotyledon leaf surface (treated group). As a control, a conidial suspension of Botrytis cinerea was dropwise inoculated onto cucumber seedlings not sprayed with the drug solution (untreated group). These were then left to stand in a moist 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 lesion area ratio using the following formula:

[0351] Control value (%) = 100 - {lesion area rate in treated area / lesion area rate in untreated area} x 100

[0352] Since all of the triazole compounds randomly selected from the triazole compounds of the present invention exhibit the effects described above, it can be understood that the triazole compounds of the present invention, including compounds not listed as examples, have a fungicidal effect and do not cause phytotoxicity to plants.

[0353] The triazole compound of the present invention has excellent fungicidal activity against pathogenic bacteria that affect agricultural and horticultural plants, is highly safe, and can be synthesized industrially advantageously. The agricultural and horticultural fungicide of the present invention can effectively control diseases of agricultural and horticultural plants.

Claims

1. A compound represented by formula (ZI) or a salt thereof: [wherein in the formula (Z-I), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; Q ２ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group, and a partial structure of the following formula (III): In B １ is a nitrogen atom or a group of the formula: NR １ B represents a group represented by ２ is a nitrogen atom or a group of the formula: NR １ B represents a group represented by ３ is a nitrogen atom or a group of the formula: NR １ B represents a group represented by １ , B ２ , and B ３ wherein one of the formulas is NR １ and the remaining two are nitrogen atoms, and R １ each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, the carbon atoms marked with * and + in the partial structure of formula (III) correspond to the carbon atoms marked with * and + in formula (Z-I), and Z ａ represents an oxygen atom or a sulfur atom, T represents the partial structure (T-1) or the partial structure (T-2), In the partial structure (T-1) or partial structure (T-2), the arrow marked with + is bonded to the carbon atom marked with + in the partial structure of formula (III), and the other arrow is bonded to the carbon atom marked with + in formula (Z-I). ７ and R ８ In the partial structure (T-1), Z represents an oxygen atom or a sulfur atom, and 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 heterocyclyl group, ｂ represents a C1-6 alkoxy group or a C1-6 alkylthio group, 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 heterocyclyl group, or a halogeno group; R ８ 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 heterocyclyl group, or a halogeno group; R 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- or 6-membered heterocyclyl group, or a halogeno group; R ５ each independently represent 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- or 6-membered heterocyclyl group, or a halogeno group, and R ４ and R ５ may combine with each other to form a divalent organic group, and n represents an integer of 0 to 3.

2. The compound or salt thereof according to claim 1, wherein said formula (ZI) is represented by formula (I). [wherein in the formula (I), Q １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ , R ８ and n is Q in formula (Z-I). １ , Q ２ , B １ , B ２ , B ３ , Z ａ , R ４ , R ５ , R ７ , R ８ and n have the same meaning as Z and R ６ represents Z and R in the partial structure (T-1). ６ It has the same meaning as 3. The compound or salt thereof according to claim 1, wherein the formula (ZI) is represented by formula (II): [wherein in the formula (II), Q １ , Q ２ , Z ａ , R ４ , R ５ , R ７ , R ８ and n is Q in formula (Z-I). １ , Q ２ , Z ａ , R ４ , R ５ , R ７ , R ８ and n have the same meaning as R １ is R in the formula (III). １ and Z and R ６ represents Z and R in the partial structure (T-1). ６ It has the same meaning as 4. An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compound and its salts according to any one of claims 1 to 3.

5. The agricultural and horticultural fungicide according to claim 4, which is used for seed treatment.

6. The agricultural and horticultural fungicide according to claim 4, further comprising other active ingredients.

7. The other active ingredients are nucleic acid biosynthesis inhibitors, mitosis inhibitors, cell division inhibitors, respiration 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, agents with multiple sites of action, biological preparations 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, glutamatergic chloride ion channel allosteric modulators, juvenile hormone analogs, non-specific inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, and microbial-derived insect midgut lining agents. The agricultural and horticultural fungicide according to claim 6, which is at least one selected from the group consisting of disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers that disrupt the proton gradient, nicotinic acetylcholine receptor channel blockers, chitin biosynthesis inhibitor type 0, chitin biosynthesis inhibitor type 1, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complex III inhibitors, mitochondrial electron transport chain complex I inhibitors, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, mitochondrial electron transport chain complex IV inhibitors, mitochondrial electron transport chain complex II inhibitors, ryanodine receptor modulators, chordotonal organ modulators with unspecified target sites, and GABA-gated chloride ion channel allosteric modulators.

8. The other active ingredients are: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clozylacon, ofrace; bupirimate, dimethirimol, ethirimol; hymexazole, octhilinone; oxolinic acid; ipflufenoquin, quinofumelin; benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, ethaboxam; pencycuron; fluopicolide, fluopimomide; fenamacryl, metrafenone, pyriophenone; pyridaclomethyl; diflumetrim, tolfenpyrad, fenazaquin; Benodaniil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenfuram, flumecyclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pydiflumetofen, isoflucipram, pyraziflumid, inpirfluxam; Azoxystrobin, cumoxystrobin, methoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopiricarb, kresoxim-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, methyltetraprole, mandestrobin; cyazofamid, amisulbrom, fenpicoxamide, florylpicoxamide; binapacryl, meptyldinocap, dinocap, fluazinam; fentin acetate, fentin chloride, fentin hydroxide; silthiofam; ametoctrazine; andoprim, cyprodinil, mepanipyrim, pyrimethanil; Blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline; tavaborole; quinoxyfen, proquinazide;Fenpiclonil, fludioxonil, chlozolinate, dimethaclon, iprodione, procymidone, vinclozolin; edifenphos, iprobenfos, pyrazophos, isoprothiolane; biphenyl, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl, etridiazole; iodocarb, propamocarb, propamocarb hydrochloride, propamocarb focetylate, prothiocarb; extract of Goseikan; natamycin; Triforine, pyrifenox, pyrisoxazole, fenarimol, flurprimidol, nuarimol, imazalil, imazalil sulfate, oxpoconazole, oxpoconazole fumarate, pefurazoate, prochloraz, triflumizole, biniconazole, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaco nazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefentrifluconazole; Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; fenhexamid, fenpyrazamine; pyributicarb, naftifine, terbinafine; polyoxin, polyoxolim; dimethomorph, flumorph, pyrimorph, benthiavalicarb, benthiavalicarb isopropyl, iprovalicarb, valifenalate, mandipropamid; fthalide, pyroquilon, tricyclazole; carpropamid, diclocymet, fenoxanil; tolprocarb; acibenzolar-S-methyl, probenazole, tiadinil, isotianil, diclobenthiazox; ipfentrifluconazole, laminarin, giant knotweed extract;Fosetyl aluminum, fosetyl calcium, fosetyl sodium, phosphoric acid, phosphate salts, phosphorous acid, phosphites; cymoxanil, tecloftalam, triazoxide, flusulfamide, diclomedine, cyflufenamid, dodine, dodine free base, flutianil, ferimzone, tebufloquine, picarbutrazox, validamycin; Copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Ambam, Ferbam, mancozeb, maneb, mancopper, metiram, metiram zinc, polycarbamate, propineb, thiram, zineb, ziram; Captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine tribesylate, anilazine, dithianone, chinomethionate, fluorimide, metasulfocarb; DBEDC, Fluorofolpet, Bis(8-quinolinolato)copper(II), Propamidine, Chloropicrin, Cyprofuram, Agrobacterium, Bethoxadin, Diphenylamine, Methylisothiocyanate (MITC), Mildeomycin, Capsaicin, Kufuraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Difenzoquat, Difenzoquat Methylsulfonate, Flumetober, Irmamycin, Nitrotarisopropyl, Oxamocarb, Pyrrolnitrin, Tolnifanide, Zaliramide, Argophase, Amicarthiazole, Oxathiapiproline, Fluoxapiproline, Benthiazole, Trichlamide, Uniconazole, Oxfenthiin, Pyrapropoin, Fluindapyr, Aminopyrifen, Dipimethitron, Flufenoxadiazam, Flumethylsulfolim, Feneptamidoquin; Trichoderma atroviride strain I-1237, Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1, Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B; Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum strain T-22; Trichoderma virens strain G-41;Clonostachys rosea strain J1146, Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON / M / 91-08; Hanseniaspora ubaraum strain BC18Y; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisiae strain LAS02, Saccharomyces cerevisiae strain DDSF623; Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens FZB24 strain, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332; Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis HAI-040 Four strains: Bacillus subtilis strain RTI477; Bacillus veresensis strain RTI301; PHC25279; Gluconobacter selinus strain BC18B; Pseudomonas chlororaphis strain ASF009; Pseudomonas rhodesiae strain HAI-0804; Streptomyces griseoviridis strain K61, and Streptomyces ridicus strain WYEC108; Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb; fenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixycarb, aminocarb, bufencarb, cloethocarb, metam sodium, promecarb;Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, fenflur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyaphos, isofenphos, isocarbophos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, para Thionemethyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, fonofos, formothion, fosmetilan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos; Chlordane, endosulfan, ethiprole, fipronil; acetoprole, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor, flufiprole;Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, 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, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadesrin, permethrin, fenothrin phosphorus [(1R)-trans isomer], prallethrin, pyrethrum, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyrithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbut, pyresmethrin, telallethrin, κ-bifenthrin, chloroprallethrin, heptafluthrin, meperfluthrin, ε-metofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin, bioethanomethrin; DDT, methoxychlor; acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, nicotine, sulfoxaflor, flupyradifurone, dichloromezothiaz, phenmezodithiaz, triflumezopyrim, flupirimine; spinetoram, spinosad; abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;Hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen; diofenolan, epofenonane, triprene; 1,3-dichloropropene, methyl bromide, alkyl halides, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metam potassium salt, metam sodium salt; pymetrozine, pyrifluquinazone, afidopiropen; clofentezine, diflobidazine, hexythiazox, etoxazole; Bacillus thuringiensis subsp. israerensi, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, proteins found in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus; diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon; chlorfenapyr, DNOC, sulfluramide; binapacryl, dinobuton, dinocap; bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt; nereistoxin; Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron; buprofezin, fluazuron; buprofezin; cyromazine; chromafenozide, halofenozide, methoxyfenozide, tebufenozide; amitraz; demiditraz, chlordimeform; hydramethylnon, acequinocyl, fluacrypyrim, bifenazate; fenazaquin, fenpyroximate, pyridaben, pyrimidifen, tebufenpyrad, tolfenpyrad, rotenone; indoxacarb, metaflumizone; spidoxamat, spirodiclofen, spiromesifen, spiropydione, spirotetramat;Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide; cyenopyrafen, cyflumetofen, piflubumid; chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetraniliprole; tetrachlorantraniliprole; flonicamid; fluxametamide, isocycloceram, brofuranilide; afoxolaner, fluralaner, lotineral, sarolaner; acinonapyr, flometoquin, ledoprona, zinzpropylidaz, oxazosulfil, azadirachtin, benzoximate, benzpyrimoxane, bromopropylate, quinomethionate, dicofol, lime sulfur, mancozeb, pyridalyl, sulfur; Cryolite, benclothiaz, amidoflumet, DCIP, phenisobromorate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossiplura, japonirua, methoxadiazone, petroleum oil, potassium oleate, tetrasulfur, triarane, afidopiropen, flufiprole, fluensulfo n, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, broflanilide, Steinernema carpocapsae, Steinernema glacerai, Pasteuria penetrans, Pecilomyces tenuipes, Pecilomyces fumosoroseus, Beauveria bassiana, Beauveria brongniartii, Metarhizium anisopliae, Verticillium lecanii, fluhexafon, cyclopyrazoflor; Fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, cambandazole; closantel, oxyclozanide, rafoxanide, niclosamide; nitroxynil, nitrosquanate; pyrantel, morantel; levamisole, tetramisole; praziquantel, epsiprantel;Cyclodiene, riania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, 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 abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothio 7. The agricultural and horticultural fungicide according to claim 6, which is at least one selected from the group consisting of benzoyl, 1-naphthylacetamide, ethychlozate, cloxifonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, and daminozide.

9. A compound represented by formula (im-1a) or a salt thereof. [In the formula (im-1a), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, U １ａ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.

10. A compound represented by formula (im-2) or a salt thereof: [In the formula (im-2), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ａ represents a substituted or unsubstituted C2-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.

11. A compound represented by formula (im-1aS) or a salt thereof. [In the formula (im-1aS), Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group, U １ａ represents a carboxyl group, a C1-6 alkoxycarbonyl group, or a halogenocarbonyl group.

12. A compound represented by the formula (im-2S) or a salt thereof. [wherein, Q １ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, or a substituted or unsubstituted 9- to 10-membered heterocyclyl group; R １ represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C3-6 cycloalkyl group.

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