JP2022175130A - Oxadiazole compounds and agricultural and horticultural microbicides - Google Patents

Abstract

To provide: oxadiazole compounds which are excellent in microbicidal activity and safety and can be industrially advantageously synthesized; and agricultural and horticultural microbicides containing the same as an active ingredient.SOLUTION: The invention provides compounds represented by formula (I) or salts thereof, and agricultural and horticultural microbicides containing as an active ingredient at least one selected therefrom. In formula (I), R represents a C1-6 alkoxy group or C1-6 haloalkoxy group.SELECTED DRAWING: None

Description

The present invention relates to oxadiazole compounds and agricultural and horticultural fungicides. More specifically, the present invention relates to an oxadiazole compound that has excellent fungicidal activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing it as an active ingredient.

In the cultivation of agricultural and horticultural crops, many control agents have been proposed against crop diseases. Most of the proposed control agents are insufficient in their control efficacy, their use is restricted due to the emergence of drug-resistant pathogens, they cause phytotoxicity or contamination of plants, or they are toxic to humans, livestock and fish. and the impact on the environment is large, so it is not fully satisfactory. Therefore, there is a strong demand for development of a pest control agent that can be safely used without such drawbacks.

By the way, Patent Literature 1 discloses a compound represented by the formula (A) and the like.

WO 2019/022061 A1

An object of the present invention is to provide an oxadiazole compound that has excellent fungicidal activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing it as an active ingredient.

式(I)中、Ｒは、Ｃ１～６アルコキシ基またはＣ１～６ハロアルコキシ基を示す。 The present invention includes the following forms.
[1] A compound represented by formula (I) or a salt thereof.

In formula (I), R represents a C1-6 alkoxy group or a C1-6 haloalkoxy group.

[2] An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] and salts thereof.
[3] The agricultural and horticultural fungicide of [2], which is for seed treatment.

INDUSTRIAL APPLICABILITY The oxadiazole compound of the present invention has excellent bactericidal activity, reliable effects, excellent safety, and can be industrially advantageously synthesized. The agricultural and horticultural fungicide of the present invention has an excellent control effect, does not cause phytotoxicity to plants, has little toxicity to humans, livestock and fishes, and has little impact on the environment.

The oxadiazole compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I).

In formula (I), R represents a C1-6 alkoxy group or a C1-6 haloalkoxy group.

The "C1-6 alkoxy group" for R may be linear or branched as long as it has 3 or more carbon atoms. As the "C1-6 alkoxy group", methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, i-hexyloxy group, and the like.

Examples of the "C1-6 haloalkoxy group" for R include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group and the like.

Salts of compound (I) are not particularly limited as long as they are agriculturally and horticulturally acceptable salts. For example, 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; and salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine.

Compound (I) or a salt of compound (I) is not particularly limited by its production method. Also, a salt of compound (I) can be obtained from compound (I) by a known method. For example, compound (I) or a salt of compound (I) can be obtained by the production method described in Examples and the like.

The agricultural and horticultural fungicide of the present invention contains at least one selected from the group consisting of compound (I) and salts of compound (I) as an active ingredient (hereinafter sometimes referred to as active ingredient (I)). It is something to do. The amount of the active ingredient (I) contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

The agricultural and horticultural fungicides of the present invention are suitable for a wide variety of filamentous fungi such as Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, zygotes. It can be used to control plant diseases caused by fungi belonging to Zygomycetes.

Examples of plant diseases (pathogens) targeted for control are shown below.
Sugar beet: brown spot (Cercospora beticola), cochlioides (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), spot Peanuts: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum ), rust (Alternaria alternata), white silk (Sclerotium rolfsii), black stain (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis) , Mycosphaerella melonis, Fusarium oxysporum, Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum orbiculare, Cladosporium cucumerinum, Brown spot Corynespora cassiicola, Pythium debaryanum, Rhizoctonia solani Kuhn, Phomopsis sp., Pseudomonas syringae pv. Lachrymans, etc. Tomatoes: Botrytis cinerea, leaves Mold (Cladosporium fulvum), plague (Phytophthora infestans), wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), ring spot (Alternaria solani), Pseudocercospora fuligena, Ralstonia solanacearum, Sclerotinia sclerotiorum, etc. Eggplant: Botrytis cinerea, Corynespora melongenae, Erysiphe cichoracearum), Mycovellosiella nattrassii, Sclerotinia sclerotiorum, Verticillium dahliae, Phomopsis vexans, etc. Pepper: Phytophthora capsici, Botrytis cinerea , Sclerotinia sclerotiorum, Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense, Leveillula taurica Strawberry: Botrytis cinerea, Sphaerotheca humuli , Colletotrichum acutatum, Colletotrichum fragariae, Phytophthora cactorum, Rhizopus stolonifer, Fusarium oxysporum, Verticillium dahliae, Sclerotinia sclerotiorum, etc. Onions: Gray Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Small fungi nucleus rot (Botrytis squamosa), dry rot (Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotium (Sclerotium cepivorum), rust (Puccinia allii), white silk disease (Sclerotium rolfsii), etc. Green onions: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rot (Sclerotium cepivorum), rust (Puccinia allii), leaf blight (Botrytis squamosa), white silk disease (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Cabbage: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), black spot (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), mildew (Peronospora parasitica), sclerotinia (Sclerotinia sclerotiorum) ), Black soot (Alternaria brassicicola), Gray mold (Botrytis cinerea), Root rot (Phoma lingam), Pythium aphanidermatum, Pythium ultimum, White rust (Albugo macrospora), etc. Lettuce: rot ( Pseudomonas cichorii, Pseudomonas marginalis, Pectobacterium carotovorum, Bremia lactucae, Botrytis cinerea, Sclerotinia sclerotiorum, Mirafiori lettuce big-vein ophiovirus, Fusarium oxysporum, Rhizoctonia solani, Golovinomyces orontii, etc. Green beans: Sclerotinia sclerotiorum, Botrytis cinere a), Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc. Peas: Mycosphaerella blight, Botrytis cinerea, Sclerotinia sclerotiorum, Erysiphe pisi )Such

Apples: powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), monilia (Monilinia mali), black spot (Mycosphaerella pomi), rot (Valsa mali), leaf spot (Alternaria mali), scab (Gymnosporangium) yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple leaf spot (Helicobasidium mompa), White leaf disease (Rosellinia necatrix), Gray mold (Botrytis cinerea), Fire blight (Erwinia amylovora), Silver leaf disease (Chondrostereum purpureum), Root canker (Rhizobium radiobacter, Rhizobium rhizogenes) Plum: Cladosporium carpophilum, Botrytis cinerea, Monilinia mumecola, Peltaster sp., Taphrina pruni, Phloeosporella padi Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), horn spot (Cercospora kaki), leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), soot spot (Zygophiala) jamaicensis), etc. Peach: Monilinia fructicola, Monilia fructigena, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans , Anthracnose (Colletotrichum gloeosporioides), Brown pit (Phloeosporella padi), Coriolus versicolor, etc. Almonds: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, leaf blight Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Cherry: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp. Monilinia kusanoi, Mycosphaerella cerasella, Podosphaera tridactyla, etc. Grapes: Botrytis cinerea, Uncinula necator, 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 disease (unidentified pathogen), root cancer (Rhizobium radiobacter, Rhizobium vitis), etc. Pear: Venturia nashicola, Gymnosporangium asiaticum, Alternaria kikuchiana Botryosphaeria berengeriana, powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Pestalotiop sis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blister (Exobasidium reticulatum), red scorch (Pseudomonas syringae), blast (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii) , Penicillium italicum, Penicillium digitatum, Botrytis cinerea, Diaporthe citri, Xanthomonas campestris pv. Citri, Powdery mildew (Oidium sp.), Late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava, Pseudomonas syringae, Botrytis cinerea, fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), Pseudocercospora actinidiae, etc. Olive: Colletotrichum acutatum, Colletotrichum gloeosporioides, Peacock spot (Spilocaea oleaginea), etc. Chestnut: Colletotrichum gloeosporioides, etc.

Wheat: Powdery mildew (Blumeria graminis f.sp. tritici), Fusarium head blight (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Fusarium rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Pythium iwayamai, Monographella nivalis, Pseudocercosporella herpotrichoides, Septoria tritici, Leptosphaeria nodorum, Typhula incarnata), Myriosclerotinia borealis, Gaeumannomyces graminis, Claviceps purpurea, Tilletia caries, Ustilago nuda, Pyricularia grisea ), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: Pyrenophora graminea, Pyrenophora teres ), Rhynchosporium secalis, Naked smut (Ustilago tritici, U.nuda), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp. Rice: Pyricularia oryzae, Rhizoctonia solani, Gibberella fujikuroi, Cochliobolus miyabeanus, Pythium graminicola), Xanthomonas oryzae, Burkholderia plantarii, Acidovorax avenae, Burkholderia glumae, Cercospora oryzae, Rice blight (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Alternaria padwickii, Epicoccum purpurascens, etc. Tobacco: Sclerotinia sclerotiorum, Erysiphe cichoracearum, plague ( Phytophthora nicotianae), etc. Tulips: Botrytis cinerea, Botrytis tulipae, Rhizoctonia solani, Fusarium oxysporum, Rhizoctonia solani, etc. Rose: Black star Diplocarpon rosae, powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Peronospora danica), Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum, Rhizoctonia solani, Fusarium solani, etc. Gerbera: Botrytis cinerea ), powdery mildew (Podosphaera xanthii), etc. Lily: leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflower: downy mildew (Pl asmopara halstedii), Sclerotinia sclerotiorum, Botrytis cinerea, etc. Bentgrass: Sclerotinia borealis, Large patch (Rhizoctonia solani), Brown patch (Rhizoctonia solani), Dollar spot ( Sclerotinia homoeocarpa), Pyricularia sp., Pythium aphanidermatum, Colletotrichum graminicola, etc. Orchard grass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purpura (Cercospora kikuchii), downy mildew Peronospora manshurica, Phytophthora sojae, Phakopsora pachyrhizi, Sclerotinia sclerotiorum, Colletotrichum truncatum, Botrytis cinerea, 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. Potatoes: Phytophthora infestans ), Alternaria solani, Thanatephorus cucumeris, Verticillium albo-atrum, V. dahliae, V. nigrescens, Pectobacterium atrosepticum, Pectobacterium carotovorum, Gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia (Sclerotinia sclerotiorum), etc. osporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potato: Helicobasidium mompa, Fusarium oxysporum, etc. Taro: Phytophthora colocasiae, stem rot (Rhizoctonia) solani), etc. Ginger: Root rot (Pythium ultimum, Pythium myriotylum), White star disease (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum) aenigma), canker (Xanthomonas campestris), shaft 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 ( Coletotrichum coffeanum), Brown eye disease (Cercospora coffeicola), etc. Sugar cane: Brown rust (Puccinia melanocephala), etc. Corn: Gloeocercospora sorghi, rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago) maydis), leaf blight (Cochliobolus heter) ostrophus), Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. 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.

The agricultural and horticultural fungicide of the present invention can be used for cereals; vegetables; root vegetables; potatoes; fruit trees, trees such as tea, coffee and cacao; is preferred.

The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stems, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots and cuttings. . In addition, improved cultivars/varieties, cultivated cultivars, mutants, hybrids, and genetically modified organisms (GMO) of these plants can also be targeted.

The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. for the control of various diseases occurring in agricultural and horticultural crops including flowers, lawns, and pastures. can be done.

The agricultural and horticultural fungicide of the present invention may contain ingredients other than the active ingredient (I). Other components include known carriers used for formulation. In addition, as other ingredients, conventionally known fungicides, insecticides/miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. (hereinafter , sometimes referred to as active ingredient (II)). The agricultural and horticultural fungicide of the present invention may exhibit a synergistic effect by containing the active ingredient (I) and the active ingredient (II).

Specific examples of the fungicide as the active ingredient (II) that can be mixed or used together with the agricultural and horticultural fungicide of the present invention are shown below.
(1) nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clodiracone, ofrace;
(b) adenosine deaminase inhibitors: bupirimate, dimethylmol, ethylimole;
(c) DNA/RNA synthesis inhibitors: Hymexazole, Octilinone;
(d) DNA topoisomerase II inhibitor: oxolinic acid;

(2) mitotic inhibitors and cytostatic agents:
(a) beta-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, ethaboxam;
(b) a cytostatic agent: penciclon;
(c) delocalized inhibitors of spectrin-like proteins: fluopicolide, fluopimimide;

(3) respiratory inhibitors:
(a) complex I-NADH oxidoreductase inhibitors: diflumetrim, tolfenpyrad;
(b) complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, flumeciclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapirox sado, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pydiflumetofen, isoflurcipram, pyraziflumide, impylfluxam;
(c) complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, comoxistrobin, comeoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin , pyrametostrobin, triclopiricarb, cresoxime-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, methyltetraprol, mann Destrobin;
(d) complex III-ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom, fenpicoxamide;
(e) uncouplers of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap, fluazinam, ferimzone;
(f) oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethoctrazine;

(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;

(5) signaling inhibitor:
(a) signaling inhibitors: quinoxifene, proquinazide;
(b) MAP and histidine kinase inhibitors in osmotic signaling: fenpicronil, fludioxonil, clozolinate, iprodione, procymidone, vinclozolin;

(6) Lipid and Cell Membrane Synthesis Inhibitors:
(a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane;
(b) lipid peroxidants: biphenyl, chloroneb, dichlorane, quintozene, technazene, tolclofosmethyl, etridiazole;
(c) agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb;
(d) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600, Bacillus subtilis strain D747, Bacillus subtilis strain Bacillus amyloliquefaciens;
(e) Agents that disrupt cell membranes: extracts of Gosseikajeupte (tea tree);

(7) cell membrane sterol biosynthesis inhibitors:
(a) C14 demethylation inhibitors in sterol biosynthesis: Trifolin, Pyrifenox, Pyrisoxazole, Fenarimol, Flurprimidol, Nuarimol, Imazalil, Imazalil Sulfate, Oxpoconazole, Oxpoconazole Fumarate , pefurazoate, prochloraz, triflumizole, biniconazole, azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, fluquinconazole, 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, fenpropidine, piperaline, spiroxamine;
(c) 3-ketoreductase inhibitors in C4 demethylation of sterol biosynthesis: fenhexamide, fenpyrazamine;
(d) squalene epoxidase inhibitors of sterol biosynthesis: piributicarb, naftifine, terbinafine;

(8) cell wall synthesis inhibitor:
(a) a trehalase inhibitor: validamycin;
(b) chitin synthase inhibitors: polyoxins, polyoxolims;
(c) cellulose synthase inhibitors: dimethomorph, flumorph, pirimorph, bentiavalicarb, bentiavalicarb isopropyl, iprovalicarb, valifenalate, mandipropamide;

(9) Melanin biosynthesis inhibitor
(a) reductase inhibitors of melanin biosynthesis: fthalide, pyroquilone, tricyclazole;
(b) dehydratase inhibitors of melanin biosynthesis: carpropamide, diclocimet, phenoxanyl;
(c) polyketide synthesis inhibitors of melanin biosynthesis: tolprocarb;

(10) host plant resistance inducer:
(a) an agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: probenazole, tiazinyl, isotianil, diclobentiazox, ipfentrifluconazole, laminarin, porcupine extract, phosphorous acid, phosphite;

(11) agents of unknown activity: cymoxanil, fosetyl aluminum, phosphoric acid, phosphate, tecloftalam, triazoxide, fursulfamide, diclomedine, metasulfocarb, cyflufenamide, metrafenone, pyriophenone, dodine, dodine free base, flutianil;

(12) agents with multiple sites of action: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, farbum, mancozeb, maneb, Mankappa, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlorofluanid, tolylfluanid, guazatine, guazatine triacetate (also known as iminoctazine triacetate), iminoctazine trialbesylate , anilazine, dithianone, quinomethionate, fluorimide;

(13) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyproflam, agrobacterium, betoxazine, diphenylamine, methylisocyanate (MITC) ), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Difenzoquat, Difenzoquat Methylsulfonate, Flumetovel, Fosetyl Calcium, Fosetyl Sodium, Irmamycin, Natamycin, Nitrotal Isopropyl , oxamocarb, pyrrolnitrin, tebufuroquine, tolnifanide, zariramide, algophase, amicalthiazole, oxathiapiproline, fluoxapiproline, metiramzinc, benzazole, triclamamide, uniconazole, oxyfenthine, picarbutrazox, dichloro Benchiazox, Quinohumelin, Thiuram, Ambum, Agrobacterium radiobacter, Coniotylium minitans, Pseudomonas fluorescens, Pseudomonas rhodesia, Talaromyces flavus, Trichoderma atroviride, Nonpathogenic Erwinia carotovora, Bacillus simplex, variovorax paradox, lactobacillus plantarum, floryl picoxamide, pyrapropoin, fluindapyr, aminopyrifene, pyridaclomethyl, ipflufenoquine, dipimethitron;

Specific examples of insecticides/miticides, nematicides, soil pesticides, anthelmintics, etc. as active ingredient (II) that can be mixed or used together with the agricultural and horticultural fungicide of the present invention are shown below. .

(1) Acetylcholinesterase (AChE) inhibitor
(a) carbamate acetylcholinesterase (AChE) inhibitors:
alanicarb, aldicarb, bendiocarb, benfuracarb, butocaboxim, butoxycarboxim, carbaryl, carbofuran, carbosulphan, ethiophenecarb, phenocarb, formethanate, furatiocarb, isoprocarb, methiocarb, methomil, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, Thiophanox, Triazamate, Trimetacarb, XMC, Xylylcarb, Phenothiocarb, MIPC, MPMC, MTMC, Aldoxycarb, Alixcarb, Aminocarb, Bufencarb, Croetocarb, Metam Sodium, Promecarb;
(b) organophosphorus acetylcholinesterase (AChE) inhibitors:
Acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, cassafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfotone, EPN, Ethione, Ethoprophos, Fanfur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imisiaphos, Isofenphos, Isocarbophos, Isopropyl O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monochrome tofos, naled, omethoate, oxydimeton-methyl, parathion, parathion-methyl, phenthoate, folate, fosalone, phosmet, phosphamidone, phoxim, pirimiphos-methyl, propenofos, propetamphos, prothiophos, pyraclophos, pyridafenthion, quinarphos, sulfotep, tebpyrimphos, temefos, terbufos, tetra chlorbinphos, thiometone, triazophos, trichlorfon, vamidothion, bromophos ethyl, BRP, carbophenothion, cyanofenphos, CYAP, demeton-S-methylsulfone, dialiphos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, honophos, formothion, fosmethylan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos;

(2) GABAergic chloride ion (chloride ion) channel blockers:
Acetoprol, Chlordane, Endosulfan, Ethiprol, Fipronil, Pirafluprol, Pyliprol, Camphechlor, Heptachlor, Dienochlor, Flufiprol;

(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, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empentrin [(EZ)-( 1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin, permethrin, phenothrin [(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, fenpyritrin, flubrocitrinate, flufenprox, metofruthrin, protrifenbut, pyrethmethrin, terarethrin, kappa-bifenthrin, chloroprathrin, heptafluthrin, meperfluthrin, epsilon - Metofluthrin, Monfluorothrin, ε-Monfluorothrin, κ-Tefluthrin, Tetramethylfluthrin, Bioethanomethrin;
(b) sodium channel modulators (DDTs):
DDT, methoxychlor;

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators:
Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Nitiazine, Thiacloprid, Thiamethoxam, Nicotine, Sulfoxaflor, Flupyradifuron, Triflumezopyrim, Dichloromezothiaz, Flupyrimine;
(5) Nicotinic Acetylcholine Receptor (nAChR) Allosteric Modulators:
spinetoram, spinosad;
(6) Glutamatergic chloride (chloride) channel (GluCl) allosteric modulators:
abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin, milbemycin oxime, nemadectin;

(7) juvenile hormone-like agents:
Hydroprene, Quinoprene, Methoprene, Fenoxycarb, Pyriproxyfen, Diphenolane, Epophenonane, Triprene;
(8) Other non-specific (multi-site) inhibitors:
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) String tone organ TRPV channel modulators:
flonicamid, pymetrozine, pyrifluquinazone, aphidopyropene;
(10) Mites growth inhibitor:
Clofentezine, Diflovidazine, Hexythiazox, Etoxazole;
(11) Microorganism-derived insect midgut lining-disrupting agent:
Bacillus thuringiensis subsp. islaerensi, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. .105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; Bacillus sphaericus;

(12) Mitochondrial ATP synthase inhibitor:
diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifone;
(13) Oxidative phosphorylation uncouplers that perturb the proton gradient:
Chlorfenapyr, DNOC, Sulfuramide, Binapacryl, Dinobuton, Dinocap;
(14) Nicotinic Acetylcholine Receptor (nAChR) Channel Blockers:
bensultap, cartap hydrochloride, nereitoxin, thiocyclam, thiosultap-sodium salt;
(15) Chitin biosynthesis inhibitor, type 0:
bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron;
(16) chitin biosynthesis inhibitor, type 1:
buprofezin;
(17) molting inhibitor:
Cyromazine;
(18) molting hormone (ecdysone) receptor agonists:
Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide;

(19) Octopamine receptor agonists:
amitraz, demiditraz, chlordimeform;
(20) mitochondrial electron transport chain complex III inhibitor:
hydramethylnon, acequinosyl, fluacrypyrim, bifenazate;
(21) mitochondrial electron transport chain complex I inhibitor (METI):
Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad, Rotenone;
(22) voltage-gated sodium channel blockers:
indoxacarb, metaflumizone;
(23) Acetyl-CoA carboxylase inhibitors:
spirodiclofen, spiromesifen, spirotetramat, spiropidione;
(24) mitochondrial electron transport chain complex IV inhibitor:
aluminum phosphide, calcium phosphide, zinc phosphide, phosphine, cyanide, calcium cyanide, sodium cyanide, potassium cyanide;
(25) mitochondrial electron transport chain complex II inhibitor:
cyenopyrafen, cyflumetofen, piflubumide;

(28) ryanodine receptor modulators:
chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, cyhalodiamide, tetrachlorantraniliprole, tetraniliprole;
(29) Chordotome modulator Target site unspecified:
flonicamid;
(30) GABAergic chloride ion (chloride) channel allosteric modulators:
brofuranilide, fluxametamide, isocycloseram, afoxolaner, fluralaner, rotineral, sarolaner;
(31) Other insecticides, acaricides:
Azadirachtin, benzoximate, biphenazate, bromopropylate, quinomethionate, cryolite, dicofol, lime-sulfur mixture, mancozeb, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate , metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, phenoxacrim, fentriphanil, flubenzimine, fluphenazine, gossip lua, japonylua, methoxadiazon, oil, potassium oleate, tetrasul, triaracene, aphidopyropene, flufiprol, fluenesulfone , meperfluthrin, tetramethylfurthrin, tralopyril, dimefluthrin, methylneodecanamide, fluralaner, afoxolanel, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3 -yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), brofuranilide, other metadiamides, Steiner nemacapocapsae, Steiner nemagraserai, pass turia penetrans, pechyromycestenuipes, pechyromyces fumosoroseus, beauveria baciana, beauveria brongniati, metaridium anisopliae, verticillium lecani, acinonapyr, benzpyrimoxane, flometoquine, fluhexafone, Oxazosulfil, cyclopyrazofrole.

(32) Anthelmintic:
(a) Benzimidazoles: Fenbendazole, Albendazole, Triclabendazole, Oxibendazole, Mebendazole, Oxfendazole, Perbendazole, Flubendazole, Febantel, Netobimine, Thiophanate, Thiabendazole, Cambendazole;
(b) Salicylanilides: Closantel, Oxyclozanide, Rafoxanide, Niclosamide;
(c) substituted phenolic: nitroxynil, nitroscanate;
(d) pyrimidines: pyrantel, morantel;
(e) imidazothiazoles: levamisole, tetramisole;
(f) tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melarsomine, arsenamide.

Specific examples of the plant regulator as the active ingredient (II) that can be mixed or used together with the pest control agent of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, horchlorfenurone, thidiazuron, chlorfenurone, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -naphthylacetamide, ethiclozate, cloxyhonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -deoxystrigol, (+)-olobanchol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, Daminozid.

{Formulation prescription}
The agricultural and horticultural fungicide of the present invention is not particularly limited by its dosage form. Examples include dosage forms such as wettable powders, emulsions, powders, granules, water solutions, suspensions, wettable granules, and tablets. The preparation method for the formulation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.

Some formulation examples are shown below. The formulation shown below is merely an example, and can be modified within the scope of the present invention, and the present invention is in no way limited by the following formulation examples. "Parts" means "mass parts" unless otherwise specified.

(Formulation Example 1: wettable powder)
40 parts of the oxadiazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and then finely ground to obtain a hydration of 40% by weight of the active ingredient. get the drug.

(Formulation Example 2: Emulsion)
30 parts of the oxadiazole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkylallyl ether are mixed and dissolved to obtain an emulsion containing 30% by weight of the active ingredient.

(Formulation Example 3: Granules)
5 parts of the oxadiazole 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 and then finely ground, after which the particle diameter is 0.5-1. Granulate to 0 mm to obtain granules containing 5% by mass of the active ingredient.

(Formulation Example 4: Granules)
5 parts of the oxadiazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate are uniformly mixed and pulverized, then water is added thereto and kneaded. do. After that, the mixture is granulated and dried to obtain granules containing 5% by mass of the active ingredient.

(Formulation Example 5: Suspension agent)
10 parts of the oxadiazole compound of the present invention, 4 parts of polyoxyethylene alkylallyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and the particle size is 3. Wet pulverize to submicrons to obtain a suspension of 10% by weight of the active ingredient.

(Formulation Example 6: Granule wettable powder)
40 parts of the oxadiazole compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of alkylbenzenesulfonate sodium salt, 8 parts of ligninsulfonate sodium salt, and 5 parts of formaldehyde condensate of alkylbenzenesulfonate sodium salt are uniformly mixed. Mix and finely grind. Next, an appropriate amount of water is added to this and kneaded to form clay. The clay-like material is granulated and then dried to obtain a wettable powder containing 40% by mass of the active ingredient.

EXAMPLES Next, the present invention will be described more specifically by showing examples. However, the present invention is by no means limited by the following examples.

[Example 1]
4-ethoxy-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)pyridazin-3(2H)-one (compound (A-1)) Synthesis of

(Step 1): Synthesis of 4-((5-chloro-6-oxopyridazin-1(6H)-yl)methyl)benzonitrile 4-chloropyridazin-3(2H)-one (5.08 g) was 150 ml), 4-cyanobenzyl bromide (9.34 g) and potassium carbonate (10.81 g) were added thereto, and the mixture was stirred overnight at room temperature.
The resulting liquid was filtered through celite, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain the desired compound (11.14 g). Yield 100%.

(Step 2): Synthesis of 4-((5-ethoxy-6-oxopyridazin-1(6H)-yl)methyl)benzonitrile 4-((5-chloro-6-oxopyridazin-1(6H)-yl ) Methyl)benzonitrile (0.5 g) was dissolved in tetrahydrofuran (8 ml) and ethanol (0.19 g) was added. Furthermore, 60% sodium hydride (0.12 g) was added thereto under ice-cooling, and the mixture was stirred at room temperature for 2.5 hours.
The resulting liquid was cooled, added to a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off from the resulting product under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain the desired compound (0.37 g). Yield 71%.

(Step 3): Synthesis of 4-ethoxy-2-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)pyridazin-3(2H)-one 4 -((5-ethoxy-6-oxopyridazin-1(6H)-yl)methyl)benzonitrile (0.37 g) was dissolved in ethanol (15 ml), to which was added 50% aqueous hydroxylamine solution (0.19 g). In addition, the mixture was heated under reflux for 2 hours.
The resulting liquid was concentrated under reduced pressure to obtain crude N'-hydroxy-4-((5-ethoxy-6-oxopyridazin-1(6H)-yl)methyl)benzimidamide. The resulting crude product was dissolved in 15 ml of dichloromethane, trifluoroacetic anhydride (0.93 g) was added under ice-cooling, and the mixture was stirred at room temperature for 3 hours.
The resulting liquid was concentrated under reduced pressure, and the obtained concentrate was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain the target compound (0.38 g). Yield 72%.

The following compound (A-2) was produced in the same manner as in the above examples. The melting point (mp) of compound (A-2) was 122-123°C.

[Biological test]
The following test examples demonstrate that the oxadiazole compound of the present invention is useful as an active ingredient in agricultural and horticultural fungicides.

(Preparation of test emulsion)
5 parts by mass of the oxadiazole compound (active ingredient (I)) of the present invention was mixed with 93.5 parts by mass of dimethylformamide and 1.5 parts by mass of polyoxyethylene alkylaryl ether to dissolve the active ingredient (I). ) at a concentration of 5% by weight was obtained.

Control value was calculated by the following formula.
Control value (%) =
100-{lesion area ratio in treated area/lesion area ratio in untreated area}×100

(Test Example 1) Wheat leaf rust control test Water was added to the emulsion (I) to dissolve the emulsion to obtain a drug solution containing the active ingredient (I) at a concentration of 25 ppm. Subsequently, the chemical solution was sprayed on wheat seedlings (variety “Nourin No. 61”, 1-2 leaf stage) cultivated in nursery pots. After air-drying, uredospores of wheat leaf rust fungus (Puccinia recondita) were sprinkled on the wheat seedlings to which the chemical solution had been sprayed and inoculated (treated area). As a control, uredinia spores of wheat leaf rust fungus (Puccinia recondita) were sprinkled and inoculated to seedlings of wheat that had not been sprayed with the drug solution (untreated group). They were placed in a high humidity room at 20°C for one day. After that, it was allowed to stand in a low-humidity room at 20° C. for 12 days. Next, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

A wheat leaf rust prevention test was conducted on the compounds of compound numbers A-1 and A-2. All compounds had a control value of 75% or more.

(Test Example 2) Soybean rust prevention test Water was added to the emulsion (I) to dissolve it, and chemical solutions containing the active ingredient (I) at a concentration of 25 ppm or 0.4 ppm were obtained, respectively. Subsequently, the chemical solution was sprayed on soybean seedlings (cultivar “Enrei”) cultivated in pots for raising seedlings, and then air-dried. This was inoculated with uredospores of soybean rust (Phakopsora pachyrhizi) (treated group). As a control, soybean seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated group). They were placed in a high humidity room at 20°C for one day. After that, it was allowed to stand in a low-humidity room at 20° C. for 12 days. Next, the leaves of the soybean seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

A soybean rust control test was performed on the compounds of compound numbers A-1 and A-2 using a drug solution containing the active ingredient (I) at a concentration of 25 ppm. All compounds had a control value of 75% or more. A soybean rust control test was performed on the compounds of compound numbers A-1 and A-2 using a drug solution containing the active ingredient (I) at a concentration of 0.4 ppm. All compounds had a control value of 75% or more.

As described above, since the oxadiazole compound of the present invention exerts the effects as described above, the oxadiazole compound of the present invention, including compounds that could not be exemplified, has a bactericidal effect and is effective against plants. It can be understood that the compound does not cause phytotoxicity, is less toxic to humans, livestock and fish, and has less impact on the environment.

Claims (3)

A compound represented by formula (I) or a salt thereof.

In formula (I), R represents a C1-6 alkoxy group or a C1-6 haloalkoxy group. An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and salts thereof. The agricultural and horticultural fungicide according to claim 2, which is for seed treatment.