Cyclopropanecarboxylate compounds and uses thereof

Abstract

The present invention provides a compound having excellent control effect on plant diseases. The compound represented by formula (I) [wherein R represents a chlorine atom or a hydroxyl group.] has excellent control effect on plant diseases.

Description

Technical Field

[0001] This patent application claims priority and benefits under the Paris Convention based on Japanese Patent Application No. 2023-216472 (filed on December 22, 2023), the entire contents of which are incorporated into this application by reference.

[0002] The present invention relates to cyclopropanecarboxylate compounds and uses thereof. Background Art

[0003] Previously, various compounds have been studied and put into practical use for the purpose of preventing plant diseases (see Non-Patent Document 1). In addition, Patent Document 1 describes an ester compound represented by formula (A) (hereinafter referred to as Compound A) as a compound having excellent insecticidal activity.

[0004] [Chemical formula 1]

[0005]

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: Japanese Patent Application Publication No. 2000-63329

[0009] Non-patent literature

[0010] Non-patent document 1: The Pesticide Manual-17th edition (published by BCPC) ISBN 978-1-901396-88-1 Summary of the invention

[0011] Problems to be solved by the invention

[0012] An object of the present invention is to provide a compound having an excellent control effect on plant diseases.

[0013] Means for solving problems

[0014] The inventors of the present application have conducted studies to find a compound having an excellent control effect on plant diseases, and as a result, have found that a compound represented by the following formula (I) has an excellent control effect on plant diseases.

[0015] The present invention is as follows.

[0016] [1] A compound represented by formula (I) (hereinafter referred to as the compound of the present invention).

[0017] [Chemical formula 2]

[0018]

[0019] [In the formula, R represents a chlorine atom or a hydroxyl group.]

[0020] [2] The compound according to [1], wherein the compound represented by formula (I) is a compound represented by formula (II).

[0021] [Chemical formula 3]

[0022]

[0023] [In the formula, R has the same meaning as above.]

[0024] [3] The compound according to [1], wherein R is a chlorine atom.

[0025] [4] The compound according to [2], wherein R is a chlorine atom.

[0026] [5] The compound according to [1], wherein R is a hydroxyl group.

[0027] [6] The compound according to [2], wherein R is a hydroxyl group.

[0028] [7] A composition comprising the compound according to any one of [1] to [6] and an inactive carrier.

[0029] [8] A method for controlling plant diseases, which is carried out by treating plants or soil with an effective amount of the compound according to any one of [1] to [6].

[0030] [9] A composition comprising the compound according to any one of [1] to [6] and one or more compounds selected from the group consisting of metofluthrin and transfluthrin.

[0031]

[10] A composition comprising the compound described in any one of [1] to [6] and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils.

[0032]

[11] A composition comprising the composition described in [9] and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils.

[0033]

[12] A composition comprising the compound described in any one of [1] to [6] and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters and sugar alcohol derivatives.

[0034]

[13] A composition comprising the composition described in [9] and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters and sugar alcohol derivatives.

[0035]

[14] A composition comprising the compound according to any one of [1] to [6] and at least one thickener selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers.

[0036]

[15] A composition comprising the composition according to [9] and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers.

[0037]

[16] A composition comprising the compound described in any one of [1] to [6] and one or more antioxidants selected from the group consisting of BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0038]

[17] A composition comprising the composition described in [9] and one or more antioxidants selected from the group consisting of BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0039]

[18] A composition comprising the compound according to any one of [1] to [6] supported on a plant powder.

[0040]

[19] A composition obtained by supporting the composition described in [9] on a plant powder.

[0041]

[20] A composition comprising the compound according to any one of [1] to [6] and a binder.

[0042]

[21] A composition comprising the composition according to [9] and a binder.

[0043]

[22] A composition comprising the compound according to any one of [1] to [6] supported on one or more substrates selected from the group consisting of cotton linters and pulp.

[0044]

[23] A composition obtained by supporting the composition according to [9] on one or more substrates selected from the group consisting of cotton linter and pulp.

[0045]

[24] A composition obtained by supporting the compound according to any one of [1] to [6] on a thermoplastic resin or paper.

[0046]

[25] A composition obtained by supporting the composition according to [9] on a thermoplastic resin or paper.

[0047]

[26] A preparation containing the compound according to any one of [1] to [6], wherein the preparation is selected from the group consisting of an oil, an emulsion, a flowable, an aerosol, a heated transpiration agent, a non-heated transpiration agent, a mist and a ULV agent.

[0048]

[27] A preparation containing the composition described in [9], wherein the preparation is selected from the group consisting of oil, emulsion, flowable, aerosol, heated transpiration agent, non-heated transpiration agent, mist and UL V agent.

[0049] Effects of the Invention

[0050] The present invention can prevent and control plant diseases. DETAILED DESCRIPTION

[0051] Among the compounds of the present invention, the compound wherein R is a chlorine atom is specifically a compound represented by formula (I-1).

[0052] [Chemical formula 4]

[0053]

[0054] Among the compounds of the present invention, the compound wherein R is a hydroxyl group is specifically a compound represented by formula (I-2).

[0055] [Chemical formula 5]

[0056]

[0057] The compounds of the present invention may contain one or more stereoisomers. Examples of stereoisomers include enantiomers and diastereomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0058] Examples of the stereoisomers of the compound of the present invention include compounds represented by formula (II).

[0059] [Chemical formula 6]

[0060]

[0061] [In the formula, R has the same meaning as above.]

[0062] The 2,2-dimethylcyclopropyl group in the compound of the present invention is preferably a 1R, trans isomer, that is, a 1R, 3R isomer. The compound is an optically active form represented by formula (II).

[0063] As the compound of the present invention, it is preferred to use an optically active substance represented by formula (II) or an isomer mixture containing a large amount of the optically active substance.

[0064] Specific examples of the stereoisomers of the compound of the present invention include a compound represented by formula (II-1) and a compound represented by formula (II-2).

[0065] [Chemical formula 7]

[0066]

[0067] [Chemical formula 8]

[0068]

[0069] As embodiments of the compound of the present invention, the following compounds can be mentioned.

[0070] The compounds of the present invention include compounds wherein R is a chlorine atom.

[0071] A compound represented by formula (I-1).

[0072] The compounds of the present invention include compounds wherein R is a hydroxyl group.

[0073] A compound represented by formula (I-2).

[0074] A compound represented by formula (II).

[0075] A compound represented by formula (II) wherein R is a chlorine atom.

[0076] A compound represented by formula (II-1).

[0077] A compound represented by formula (II) wherein R is a hydroxyl group.

[0078] A compound represented by formula (II-2).

[0079] An optically active substance represented by formula (II) or an isomer mixture containing a large amount of the optically active substance.

[0080] An optically active substance represented by formula (II-1) or an isomer mixture containing a large amount of the optically active substance.

[0081] An optically active substance represented by formula (II-2) or an isomer mixture containing a large amount of the optically active substance.

[0082] The composition as one embodiment of the present invention is a composition containing the compound of the present invention and an inactive carrier. The aforementioned composition is usually a mixture of the compound of the present invention and an inactive carrier such as a solid carrier, a liquid carrier, a surfactant, and other preparation adjuvants as needed, and is formulated into emulsions, oils, powders, granules, wettable powders, water-dispersible granules, flowables, dry suspensions, microcapsules, etc.

[0083] The aforementioned composition usually contains 0.0001 to 95% by weight of the compound of the present invention based on the total weight of the composition.

[0084] Examples of the solid carrier used in formulation include clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), fine powders and granules, and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).

[0085] Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).

[0086] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether or salts thereof (polyoxyethylene alkyl ether ammonium sulfate), polyoxyethylene alkyl aryl ether or salts thereof, and polyethylene glycol fatty acid esters; and anionic surfactants such as alkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.

[0087] Examples of other formulation adjuvants include fixatives, dispersants, colorants, stabilizers, and the like, and specific examples include casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0088] The compounds of the present invention are effective against plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, phytomyxea, and bacteria, and can prevent and cure the plant diseases. Examples of fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specifically, examples include the following. The scientific name of the plant pathogenic microorganism that causes the disease is shown in brackets.

[0089] Diseases of rice: blast (Pyricularia oryzae), flax leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), seedling blight (Gibberella fujikur oi), yellow wilt (Sclerophthora macrospora), rice blast and panicle blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), pseudo sheath blight (red sclerotinia (Waitea circinata), brown sclerotinia (Ceratobasidium setariae), brown sheath blight (Thanatephorus cucumeris));

[0090] Diseases of wheat: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Pu cciniarecondita), red snow rot (Microdochium nivale, Mic rodochium majus), small snow rot (Typhula inc arnata, Typhula ishikariensis), large snow rot (Sclerotinia borealis), brown snow rot (Pythium spp.), loose smut (Ustilago tritici), bunt (Tilletia caries, Tilletia controversa), eye spot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), glumen blight (Stagonospora nodorum), yellow spot (Pyrenophora ritici-repentis), damping-off caused by Rhizoctonia (Rhizoctonia solani), damping-off (Gaeumanno myces graminis), blast (Pyricularia graminis-tritici);

[0091] Diseases of barley: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenae, Fusarium serrata, Microsporum snow mold), yellow rust (Puccinia stripe), black rust (Puccinia stem), stripe rust (Puccinia hordei), loose smut (Ustilago nuda), moire (Rhynchosporium secalis), web spot (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf stripe (Pyrenophora graminea), column septum leaf spot (Ramularia collo-cygni), damping off caused by Rhizoctonia (Rhizoctonia solani);

[0092] Diseases of corn: Rust (Puccinia sorghi), Southern Rust (Puccinia polysora), Large Leaf Spot (Se tosphaeria turcica), Tropical Rust (Physopella zeae), Flax Leaf Blight (Cochliobolusheterostrophus), Anthracnose (Colletotrichum graminicola), Gray Leaf Spot (Cercospora zeae-maydis), Brown Leaf Spot (Kabatiella zeae), Dark Leaf Spot (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminicola, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago may dis), stalk rot (Physoderma maydis), black smut (Phyllachora maydis);

[0093] Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola);

[0094] Coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola);

[0095] Diseases of rapeseed: Sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), pale leaf spot (Pyrenopeziza brassicae);

[0096] Sugarcane diseases: rust (Puccinia melanocephela, Pucciniakuehnii), smut (Ustilago scitaminea);

[0097] Diseases of sunflower: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii);

[0098] Diseases of citrus: melanosis (Diaporthe citri), scab (Elsinoe fawcetti), penicillium rot (Penicillium digitatum), penicillium (Penicillium italicum), blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus (Aspergillus niger);

[0099] Apple diseases: Blossom rot (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerell a cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae), Gymnosporangium yamadae);

[0100] Pear diseases: black spot (Venturia nashicola, Venturia apirina), black spot (Alterna ria alternata Japanese pearpathotype), red spot (Gymnosporangium haraeanum);

[0101] Peach diseases: gray spot disease (Monilinia fructicola), black spot disease (Cladosporium carpophilum), brown streak disease (Phomopsis rot) (Phomopsis sp.), leaf curl disease (Taphrina deformans);

[0102] Diseases of grapes: black pox (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmo para viticola);

[0103] Persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf fall (Cercospora kaki, Mycosphaerella nawae);

[0104] Diseases of figs: rust (Phakopsora nishidana);

[0105] Diseases of cucurbits: anthracnose (Colletotrichum lagenar ium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), blight (Phytophthora capsici), damping-off (Pythium sp.), and Phomopsis root rot (Phomopsis sp.).

[0106] Diseases of tomatoes: ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), sooty mold (Pseudocercospora fuligena), blight (Phytophthora infestans), powdery mildew (Leveillula taurica);

[0107] Eggplant diseases: brown streak (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);

[0108] Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophorabrassicae), downy mildew (Peronospora parasitica), white rust (Albugocandida);

[0109] Diseases of onions: rust (Puccinia allii), black spot (Alternariaporri), black rot (Sclerotium cepivorum), small sclerotium neck rot (Botrytis squamosa);

[0110] Diseases of soybean: purple spot (Cercospora kikuchii), black pox (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring rot (Corynesp ora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), damping-off (Rhizoctonia solani), brown streak (Septoria glycines), spot (Cercospora sojina), sclerotinia (Sclerotinia sclerotiorum), powdery mildew (Microsphaeradiffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death syndrome (Fusarium virguliforme), red crown rot (Calonectria ilicicola), the Diaporthe / Phomopsis complex (Diaporthe longicolla);

[0111] Diseases of beans: sclerotinia (Sclerotinia sclerotiorum), rust (Uromyces appendiculatus), angular leaf spot (Phae oisariopsis griseola), anthracnose (Colletotrichum lindem uthianum), root rot (Fusarium solani);

[0112] Diseases of peanut: black spot (Cercospora personata), brown spot (Cercospora arachidicola), white rot (Sclerotium rolfsii), red crown rot (Calone ctria ilicicola);

[0113] Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);

[0114] Potato diseases: early blight (Alternaria solani), blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f.sp.subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), cancer (Synchytrium endobioticum);

[0115] Strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum);

[0116] Tea diseases: web cake disease (Exobasidium reticulatum), white star disease (Elsinoe leucospila), gray blight (Pestalotiopsis sp.), anthracnose (Colletotrichum thea e-sinensis);

[0117] Diseases of tobacco: brown spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthora nicotianae);

[0118] Diseases of sugar beet: brown spot (Cercospora beticola), leaf blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (aphanomyces root rot) (Aphanomyces cochlioides), rust (Uromyces betae);

[0119] Rose diseases: scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);

[0120] Diseases of chrysanthemum: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);

[0121] Onion diseases: botrytis leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotinia neck rot (Botrytis squamosa);

[0122] Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia (Sclerotinia sclerotiorum), black rot (Sclerotium cepivorum), white rot (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum);

[0123] Radish diseases: black spot (Alternaria brassicicola);

[0124] Lawn grass diseases: Dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), Pythium wilt (Pythium aphanidermatum);

[0125] Banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola);

[0126] Diseases of lentils: Ascochyta disease (Ascochyta lentis);

[0127] Chickpea diseases: Ascochyta rabiei;

[0128] Diseases of green peppers: Anthracnose (Colletotrichum scovill ei);

[0129] Diseases of mango: Anthracnose (Colletotrichum ac utatum);

[0130] Diseases of sweet potatoes: Basal rot (Diaporthe destruens);

[0131] Fruit tree diseases: white feather disease (Rosellinia necatrix), purple feather disease (Helicobasidium mompa);

[0132] Diseases of apples, pears and other fruits after harvest: Mucor rot diseases (Mucorpiriformis);

[0133] Seed diseases or early growth diseases caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia and Diplodia;

[0134] Viral diseases: giant vein disease of lettuce mediated by Olpidium brassicae, viral diseases of various crops mediated by Polymyxa (e.g. Polymyxa beta e and Polymyxa graminis);

[0135] Diseases caused by bacteria: rice bacterial seedling blight (Burkholderia plantarii), rice inner glume browning disease (Pantoea ananatis), rice bacterial leaf blight (Xanthomonas or yzae pv.oryzae.), cucumber bacterial angular spot (Pseudomonas syringaepv.lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiesi), corn internal wilt (Clavibacter michiganensis), crown gall of grapes, olives, peaches, etc. (Xylella fastidiosa), and root nodule of Rosaceae plants such as apples, peaches, and cherries (Agrobacterium tumefaciens).

[0136] Examples of the plant disease control method of the present invention include treatment of plant bodies such as stem and leaf spraying and seed disinfection, and treatment of plant cultivation sites such as soil treatment.

[0137] Regarding the treatment amount of the compound of the present invention, generally per 1000m 2 When the compound of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water to a concentration of 0.01 to 10,000 ppm (e.g., 1,000 ppm) of the active ingredient and applied. Granules, powders, etc. are usually applied directly.

[0138] The composition of the present invention can be used as a plant disease control agent in agricultural land such as dry fields, paddy fields, lawns, orchards, etc.

[0139] The composition as one embodiment of the present invention is a composition containing the compound of the present invention and at least one compound selected from the group consisting of metofluthrin and dimefluthrin (hereinafter referred to as composition A). Metofluthrin and dimefluthrin may be used alone or in combination. In addition, there are one or more stereoisomers in each of metofluthrin and dimefluthrin, and the metofluthrin and dimefluthrin used in the present invention include stereoisomers and mixtures thereof.

[0140] In composition A, the ratio of the compound of the present invention to at least one compound selected from the group consisting of metofluthrin and transfluthrin is not particularly limited, and the ratio by mass ratio (compound of the present invention: at least one compound selected from the group consisting of metofluthrin and transfluthrin) may be 100000:1 to 1:100000, 50000:1 to 1:50000, 10000:1 to 1:10 ... :10000, 1000:1~1:1000, 500:1~1:500, 100:1~1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0141] It is known that metofluthrin and transfluthrin each have excellent control effects on harmful arthropods such as harmful insects and harmful mites. Therefore, it is also expected that the composition A containing at least one compound selected from the group consisting of metofluthrin and transfluthrin will have excellent control effects on harmful arthropods. Examples of harmful arthropods include the following harmful arthropods.

[0142] Hemiptera pests: planthoppers such as the brown planthopper, brown planthopper, white-backed planthopper, leafhoppers such as the black-tailed leafhopper and the two-spotted black-tailed leafhopper, aphids, stink bugs, whiteflies, scale insects, web bugs, psyllids, etc.

[0143] Lepidoptera pests: Chilo suppressalis, rice leaf roller, Indian grain moth and other borers, Spodoptera litura, armyworm, cabbage armyworm and other armyworms, Pieris rapae and other butterfly species, leaf rollers and other moths, fruit borers, miners, tussock moths, Spodoptera capitis, turnip moth, cutworm and other Agrotis spp. pests, Helicoverpa sp p. pests, Heliothis spp. pests, cabbage moth, straight-striped rice butterfly, clothes moth, curtain moth, etc.;

[0144] Diptera pests: Culex pipiens, Culex tritaeniorhynchus and other Culex species, Aedes aegypti, Aedes albopictus and other Aedes species, Anopheles sinensis and other Anopheles species, Chironomids, house flies, stable flies and other flies, calliphora, Sarcophagia, gray ground flies, toilet flies, onion ground flies and other flower flies, fruit flies, hairy midges, horseflies, blackflies, stable flies, etc.;

[0145] Coleoptera pests: corn rootworms such as western corn rootworm and southern corn rootworm, scarab beetles such as bronze beetle and multi-colored beetle, weevils such as corn weevils, rice water weevils, cotton boll weevils, mung bean weevils, mealworms, red flour beetles, rice mudworms, yellow flea beetles, yellow melon beetles, thief beetles, Epilachna spp., brown powder beetles, long beetles, poisonous rove beetles, etc.;

[0146] Dictyoptera pests: German cockroach, black-breasted cockroach, American cockroach, brown-spotted cockroach, oriental cockroach, etc.;

[0147] Thysanoptera pests: palm thistle, western flower thrips, flower thrips, etc.;

[0148] Hymenoptera pests: ants, wasps, scleroderma, sawflies, etc.;

[0149] Orthoptera pests: mole crickets, locusts, etc.;

[0150] Cryptoptera pests: human fleas, cat fleas, etc.;

[0151] Pediculus pests: human lice, pubic lice, etc.;

[0152] Isoptera pests: Reticulitermes truncatum, Formosan termites, etc.;

[0153] Indoor dust mites: dust mites such as dust mites, house dust mites, etc., flour mites such as tyrophagous mites, oval flour mites, secret sweet mites, house sweet mites, common hair mites, etc., Malacca carnivorous mites, Monterigan carnivorous mites, tarsal mites, scum mites, avian spiny mites, spider mites, hard ticks such as long-horned blood ticks, two-spotted spider mites, Kamisawa spider mites, citrus mites, apple mites, etc.

[0154] The harmful arthropods may be harmful arthropods whose sensitivity to pesticides, acaricides, etc. has been reduced or which have strong resistance to pesticides.

[0155] The compound of the present invention or composition A is usually used in the form of a composition (hereinafter, referred to as composition B) that also contains an inactive carrier. For composition B, the compound of the present invention or composition A can usually be mixed with a liquid carrier, a surfactant, etc., and a thickener, a binder, a dispersant, a stabilizer, a gas, and other preparation adjuvants can be added as needed, and used for oils, emulsions, wettable powders, flowable agents (water suspensions, water emulsions, etc.), powders, granules, aerosols (direct spray type, space spray type, quantitative spray type, One push type, full spray type, intermittent spray type, etc.), sprays, electrosprays (ultrasonic vibration type, electrostatic spray type, etc.), heating transpiration agents (incense sticks, electric mosquito coils, liquid wick type heating transpiration agents, etc.), non-heating transpiration agents (resin transpiration agents, impregnated paper transpiration agents, mesh preparations, etc.), smoke agents (atomizers, etc.), ULV (Ultra Low Volume, ultra-low volume) agents, etc.

[0156] The preparation as one embodiment of the present invention is a preparation selected from the group consisting of oil, emulsion, flowable, aerosol, heated transpiration agent, non-heated transpiration agent, mist and ULV agent, containing the compound or composition A of the present invention.

[0157] These preparations usually contain 0.0001 to 99% by weight of the compound or composition A of the present invention relative to the total weight of the preparation.

[0158] Examples of the liquid carrier include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, phenylxylylethane, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, methyl oleate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), amides (N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, chloroform, carbon tetrachloride, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), mineral oils (kerosene, lamp oil, light oil, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).

[0159] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A, and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils. In addition, the preparation as one embodiment of the present invention is a preparation containing the composition, selected from the group consisting of oil, emulsion, flowable agent, aerosol agent, heating evaporative agent and ULV agent.

[0160] Examples of the surfactant include alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives.

[0161] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A, and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives. In addition, the preparation as one embodiment of the present invention is a preparation selected from the group consisting of an emulsion, a flowable agent, and a heating transpiration agent containing the composition.

[0162] Examples of the thickener include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.).

[0163] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A, and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers. In addition, the preparation as one embodiment of the present invention is a flowable agent containing the composition.

[0164] Examples of the antioxidant include BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0165] The composition as one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more antioxidants selected from the group consisting of BHT and BHA. In addition, the preparation as one embodiment of the present invention is a preparation selected from the group consisting of oil, emulsion, flowable agent, aerosol, heated transpiration agent, non-heated transpiration agent, mist and ULV agent containing the composition.

[0166] The composition as one embodiment of the present invention is a composition obtained by carrying the compound of the present invention or composition A on a plant powder (wood powder, meal powder, etc.). The plant powder can also be used by mixing the above-mentioned plant powder with a binder (red nan powder, starch, gluten, etc.). In addition, the preparation as one embodiment of the present invention is a heating transpiration agent containing the composition.

[0167] A composition as another embodiment of the present invention is a composition comprising the compound or composition A of the present invention and a binder. In addition, a preparation as one embodiment of the present invention is a heat transpiration agent comprising the composition.

[0168] The composition as one embodiment of the present invention is a composition obtained by supporting the compound of the present invention or composition A on one or more substrates selected from the group consisting of cotton linters and pulp. Specifically, the substrate includes, for example, a substrate obtained by solidifying cotton linters into a plate shape and a substrate obtained by solidifying fibers of a mixture of cotton linters and pulp into a plate shape. In addition, a preparation as one embodiment of the present invention is a heating transpiration agent containing the composition.

[0169] A composition as one embodiment of the present invention is a composition obtained by supporting the compound of the present invention or composition A on a thermoplastic resin or paper. In addition, a formulation as one embodiment of the present invention is a non-heating transpiration agent containing the composition.

[0170] Examples of the resin include polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers; ethylene-methacrylate copolymers such as ethylene-methyl methacrylate copolymers and ethylene-ethyl methacrylate copolymers; ethylene-acrylate copolymers such as ethylene-methyl acrylate copolymers and ethylene-ethyl acrylate copolymers; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymers; ethylene-tetracyclododecene copolymers; polypropylene resins such as propylene polymers and propylene-ethylene copolymers; poly-4-methyl-1-pentene, poly-1-butene, polybutadiene, polystyrene, acrylonitrile- Styrene resin; styrene elastomers such as acrylonitrile-butadiene-styrene resin, styrene-conjugated diene copolymer, styrene-conjugated diene block copolymer hydrogenate; fluororesin; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and polycyclohexanedimethanol terephthalate; polycarbonate, polyacetal, polyacrylic sulfone, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, and polyurethane. These resins can be used alone or in the form of a mixture of two or more. In these resins, plasticizers such as phthalates (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, and stearic acid can also be added as needed.

[0171] Examples of the paper include filter paper and Japanese paper.

[0172] A composition as another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a thermoplastic resin.

[0173] A composition as another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on paper.

[0174] Example

[0175] Hereinafter, the present invention will be described in more detail using manufacturing examples and test examples, but the present invention is not limited to these examples.

[0176] First, production examples of the compounds of the present invention are shown.

[0177] Production Example 1

[0178] To a mixture of 1.0 g of (1R)-trans-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl ester, 10 mL of chloroform, and 246 μL of methanol was added 2.78 mL of titanium tetrachloride (1.0 M toluene solution) under ice-cooling conditions, and stirred at room temperature for 43 hours. Methanol was added to the obtained mixture, and then filtered using Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 0.39 g of a compound represented by the following formula (II-1) (referred to as the present invention compound 1).

[0179] [Chemical formula 9]

[0180]

[0181] The following shows the compound 1 of the present invention. 1 H-NMR data.

[0182] 1 H-NMR(CDCl3)δ: 5.30-5.19(2H,m),4.59(2H,s),3.58-3.42(1H,m),3.41(3H ,s),1.96-1.72(3H,m),1.58(1H,d),1.23(3H,s),1.19(3H,s),1.04(3H,t).

[0183] Production Example 2

[0184] To a mixture of 0.20 g of the compound 1 of the present invention, 5 mL of acetone, and 1 mL of water, 0.04 g of zinc oxide was added, and the mixture was stirred under heating reflux for 22 hours, and then cooled to room temperature. After adding water to the obtained mixture, it was filtered using Celite (registered trademark), and the filtrate was extracted with tert-butyl methyl ether. The obtained organic layer was dried using anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain 0.04 g of the compound represented by the following formula (II-2) (referred to as the compound 2 of the present invention).

[0185] [Chemical formula 10]

[0186]

[0187] The following shows the compound 2 of the present invention. 1 H-NMR data.

[0188] 1H-NMR(CDCl3)δ: 5.23(2H,s),4.59(2H,s),3.41(3H,s),3.28-3.20(1H,m),1.72-1.44(5H,m),1.22(3H,s),1.18(3H,s),0.97(3H,t).

[0189] Next, the efficacy of the compounds of the present invention on plant diseases is demonstrated using test examples.

[0190] It should be noted that DMSO refers to dimethyl sulfoxide. In Test Examples 1 and 2, the untreated area refers to an area tested under the same conditions as those described in the test examples except that DMSO was dispensed instead of the DMSO dilution containing the compound of the present invention.

[0191] Test Example 1: Test for controlling seedling blight (Pythium ultimum)

[0192] The compound 2 of the present invention was diluted with DMSO to contain 133 ppm, and 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of a potato extract liquid medium (PDB medium) inoculated with spores of R. solani was dispensed. The plate was cultured at 23°C for 5 days to proliferate R. solani, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of R. solani. As a result, the growth rate in the area treated with the compound 2 of the present invention was less than 5% of the growth rate in the untreated area.

[0193] Test Example 2: Control test against peach black spot fungus (Cladosporium carpop hilum)

[0194] The compound 1 of the present invention was diluted with DMSO to contain 1067 ppm, and 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of a YB liquid medium inoculated with spores of peach scab was dispensed. The plate was cultured at 18°C ​​for 5 days to proliferate peach scab, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of peach scab. As a result, the growth rate in the area treated with the compound 1 of the present invention was less than 70% of the growth rate in the untreated area.

[0195] Industrial Applicability

[0196] The compounds of the present invention show excellent control effects on plant diseases.

Claims

1. A compound represented by formula (I), [Chemical formula 1] In formula (I), R represents a hydroxyl group.

2. The compound according to claim 1, wherein The compound represented by formula (I) is a compound represented by formula (II), [Chemical formula 2] In formula (II), R represents a hydroxyl group.

3. A composition comprising the compound according to claim 1 or 2 and an inactive carrier.

4. A method for controlling damping-off of seedlings, which is carried out by treating plants or soil with an effective amount of the compound according to claim 1 or 2.

5. A composition comprising the compound according to claim 1 or 2, and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils.

6. A composition comprising the composition according to claim 3 and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils and vegetable oils.

7. A composition comprising the compound according to claim 1 or 2, and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters, and sugar alcohol derivatives.

8. A composition comprising the composition according to claim 3 and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyol esters and sugar alcohol derivatives.

9. A composition comprising the compound according to claim 1 or 2, and at least one thickener selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers.

10. A composition comprising the composition according to claim 3 and at least one thickener selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite and synthetic water-soluble polymers.

11. A composition comprising the compound according to claim 1 or 2, and one or more antioxidants selected from the group consisting of BHT and BHA, in, BHT refers to 2,6-di-tert-butyl-4-methylphenol, and BHA refers to a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol.

12. A composition comprising the composition according to claim 3 and one or more antioxidants selected from the group consisting of BHT and BHA. in, BHT refers to 2,6-di-tert-butyl-4-methylphenol, and BHA refers to a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol.

13. A composition comprising the compound according to claim 1 or 2 supported on a plant powder.

14. A composition obtained by supporting the composition according to claim 3 on a plant powder.

15. A composition comprising the compound according to claim 1 or 2 and a binder.

16. A composition comprising the composition according to claim 3 and a binder.

17. A composition comprising the compound according to claim 1 or 2 supported on at least one substrate selected from the group consisting of cotton linter and pulp.

18. A composition obtained by allowing the composition according to claim 3 to be supported on one or more substrates selected from the group consisting of cotton linter and pulp.

19. A composition obtained by supporting the compound according to claim 1 or 2 on a thermoplastic resin or paper.

20. A composition obtained by supporting the composition according to claim 3 on a thermoplastic resin or paper.

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