Ester compound and use thereof

Abstract

NOT VISIBLE DUE TO STATUS OF PATENT

Description

Ester compounds and their uses

[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application No. 2023-216476 (filed December 22, 2023), the entire contents of which are incorporated herein by reference. The present invention relates to an ester compound and uses thereof.

[0002] Various compounds have been investigated and put to practical use for the purpose of controlling plant diseases (see Non-Patent Document 1). Patent Document 1 also describes compounds of the formula (A): An ester compound represented by the formula (hereinafter referred to as Compound A) is described.

[0003] Japanese Patent Application Laid-Open No. 2000-63329

[0004] The Pesticide Manual - 17th edition (published by BCPC) ISBN 978-1-901396-88-1

[0005] An object of the present invention is to provide a compound having excellent control activity against plant diseases.

[0006] The present inventors have conducted research to find a compound having excellent control activity against plant diseases, and as a result have found that a compound represented by the following formula (I) has excellent control activity against plant diseases. The present invention is as follows. [1] Formula (I): [wherein R represents a 2-hydroxypropan-2-yl group or a 1-propen-2-yl group] (hereinafter referred to as the compound of the present invention). [2] A compound represented by formula (I) is a compound represented by formula (II): [In the formula, R has the same meaning as defined above.] [3] The compound according to [1], which is a compound represented by the formula: [3] The compound according to [1], wherein R is a 2-hydroxypropan-2-yl group. [4] The compound according to [2], wherein R is a 2-hydroxypropan-2-yl group. [5] The compound according to [1], wherein R is a 1-propen-2-yl group. [6] The compound according to [2], wherein R is a 1-propen-2-yl group. [7] A composition containing the compound according to any one of [1] to [6] and an inert carrier. [8] A method for controlling plant diseases, which comprises applying an effective amount of the compound according to any one of [1] to [6] to plants or soil. [9] A composition containing the compound according to any one of [1] to [6] and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin.

[10] A composition containing the compound according to 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.

[11] A composition containing the composition according to [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.

[12] A composition containing the compound according to any one of [1] to [6] and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.

[13] A composition containing the composition according to [9] and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonate salts, alkylaryl sulfonate salts, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.

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

[15] A composition containing 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.

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

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

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

[19] A composition in which the composition according to [9] is supported on a plant powder.

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

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

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

[23] A composition in which the composition according to [9] is supported on one or more substrates selected from the group consisting of cotton linters and pulp.

[24] A composition in which the compound according to any one of [1] to [6] is supported on a thermoplastic resin or paper.

[25] A composition in which the composition according to [9] is supported on a thermoplastic resin or paper.

[26] A formulation selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated evaporative formulations, non-heated evaporative formulations, aerosols, and ULV formulations, comprising the compound according to any one of [1] to [6].

[27] A formulation selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated evaporative formulations, non-heated evaporative formulations, aerosols, and ULV formulations, comprising the composition according to [9].

[0007] According to the present invention, plant diseases can be controlled.

[0008] In the compound of the present invention, the compound in which R is a 2-hydroxypropan-2-yl group is specifically represented by the formula (I-1): It is a compound represented by the formula:

[0009] In the compound of the present invention, the compound in which R is a 1-propen-2-yl group is specifically represented by the formula (I-2): It is a compound represented by the formula:

[0010] The compound of the present invention exists in one or more stereoisomers. Stereoisomers include optical isomers and geometric isomers. The present invention includes each optical isomer, each geometric isomer, and a mixture of isomers in any ratio.

[0011] The optical isomer of the compound of the present invention includes, for example, a compound represented by formula (II): [wherein R has the same meaning as defined above] and a compound represented by formula (III): [wherein R has the same meaning as defined above]

[0012] Specific examples of the optical isomers of the compound of the present invention include a compound represented by formula (II-1), a compound represented by formula (III-1), a compound represented by formula (II-2), and a compound represented by formula (III-2).

[0013]

[0014]

[0015]

[0016]

[0017] As the compound of the present invention, it is preferable to use an optical isomer represented by formula (II) or an isomer mixture rich in this optical isomer, and more specifically, it is preferable to use an optical isomer represented by formula (II-1) or formula (II-2) or an isomer mixture rich in this optical isomer.

[0018] The geometric isomers of the compound of the present invention include, for example, the compound represented by formula (IV): [wherein R has the same meaning as defined above]

[0019] Furthermore, the optical isomer of the compound represented by formula (IV) includes the compound represented by formula (V): [wherein R has the same meaning as defined above] and a compound represented by formula (VI): [wherein R has the same meaning as defined above]

[0020] As the compound of the present invention, it is preferable to use a geometric isomer represented by formula (I) or an isomeric mixture rich in said geometric isomer, and it is more preferable to use a geometric isomer represented by formula (V) or an isomeric mixture rich in said geometric isomer.

[0021] Embodiments of the compound of the present invention include the following compounds. A compound of the present invention in which R is a 2-hydroxypropan-2-yl group. A compound represented by formula (I-1). A compound of the present invention in which R is a 1-propen-2-yl group. A compound represented by formula (I-2). A compound represented by formula (II). A compound represented by formula (II) in which R is a 2-hydroxypropan-2-yl group. A compound represented by formula (II-1). A compound represented by formula (II) in which R is a 1-propen-2-yl group. A compound represented by formula (II-2). A mixture containing a compound represented by formula (II) and a compound represented by formula (III). An optical isomer mixture enriched with the optical isomer represented by formula (II). An optical isomer mixture enriched with the optical isomer represented by formula (II-1). An optical isomer mixture enriched with the optical isomer represented by formula (II-2). A mixture comprising a compound represented by formula (I) and a compound represented by formula (IV). A geometric isomer mixture enriched in the geometric isomer represented by formula (I). A mixture comprising a compound represented by formula (II) and a compound represented by formula (V). A geometric isomer mixture enriched in the geometric isomer represented by formula (II).

[0022] A composition that is one embodiment of the present invention is a composition containing the compound of the present invention and an inert carrier. The composition is typically prepared by mixing the compound of the present invention with an inert carrier such as a solid carrier or a liquid carrier, and optionally adding a surfactant or other formulation adjuvants to formulate it into an emulsifiable concentrate, oil concentrate, dust, granule, wettable powder, water dispersible granule, flowable concentrate, dry flowable concentrate, microcapsule concentrate, or the like. The composition typically contains the compound of the present invention in an amount of 0.0001 to 95% by weight based on the total weight of the composition.

[0023] Examples of solid carriers used in formulation include fine powders and granules of 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.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, etc.; nylon resins such as nylon-6, nylon-11, nylon-66, etc.; polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, etc.).

[0024] Examples of liquid carriers 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.).

[0025] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers or salts thereof (polyoxyethylene alkyl ether sulfate ammonium salts), polyoxyethylene alkyl aryl ethers or salts thereof, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.

[0026] Other formulation adjuvants include adhesives, dispersants, colorants, stabilizers, and the like, specific examples of which include casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl 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).

[0027] The compound of the present invention is effective against plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, Phytomyxea, and bacteria, and can control the plant diseases. Examples of fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following: The scientific name of the plant pathogenic microorganism that causes the disease is shown in parentheses.

[0028] Diseases of rice: blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), foolish seedling disease (Gibberella fujikuroi), yellowing and withering disease (Sclerophthora macrospora), false blast and panicle blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), suspected sheath blight (red sclerotium pathogen (Waitea circinata), brown sclerotium pathogen (Ceratobasidium setariae), brown sheath blight pathogen (Thanatephorus cucumeris)); 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), brown rust (Puccinia recondita), pink snow mold (Microdochium nivale, Microdochium majus), snow scab (Typhula incarnata, Typhula ishikariensis), large snow scab (Sclerotinia borealis), brown snow rot (Pythium spp.), loose smut (Ustilago tritici), bunt (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blotch (Septoria tritici), glume blotch (Stagonospora nodorum), tan spot (Pyrenophora tritici-repentis), seedling blight caused by Rhizoctonia solani, foot rot (Gaeumannomyces graminis), blast (Pyricularia graminis-tritici);Barley diseases: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), ear bunt (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), leaf spot (Ramularia collo-cygni), seedling damping-off (Rhizoctonia solani); corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty blight (Setosphaeria turcica), tropical rust (Physopella zeae), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma maydis, tar spot (Phyllachora maydis);Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola); coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); rapeseed diseases: sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae); sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger;Apple diseases: Monilinia mali, canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: black spot (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red spot (Gymnosporangium haraeanum); Peach diseases: brown rot (Monilinia fructicola), black spot (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), leaf crinkle (Taphrina deformans); grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola); persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf drop (Cercospora kaki, Mycosphaerella nawae); fig diseases: rust (Phakopsora nishidana);Cucurbit diseases: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Blight (Didymella bryoniae), Brown spot (Corynespora cassiicola), Blight (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Late blight (Phytophthora capsici), Damping-off (Pythium sp.), Root rot (Phomopsis sp.); Tomato diseases: Ring spot (Alternaria solani), Leaf mold (Cladosporium fulvum), Sooty mold (Pseudocercospora fuligena), Late blight (Phytophthora infestans), Powdery mildew (Leveillula taurica); Eggplant diseases: Brown spot (Phomopsis vexans), Powdery mildew (Erysiphe cichoracearum); Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida); Diseases of leeks: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotial rot (Botrytis squamosa);Soybean diseases: Purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Diseases of peanuts: black spot (Cercospora personata), brown spot (Cercospora arachidicola), southern blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);Potato diseases: summer blight (Alternaria solani), late 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), canker (Synchytrium endobioticum); strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum); tea diseases: net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), ring spot (Pestalotiopsis Diseases of tobacco: red spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); Diseases of sugar beet: brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root rot (Aphanomyces cochlioides), rust (Uromyces betae); Diseases of rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases of chrysanthemum: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); Onion diseases: white spotted leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotial rot (Botrytis squamosa);Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), southern blight (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); diseases of radish: black spot (Alternaria brassicicola); diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), and red blight (Pythium aphanidermatum); diseases of banana: Sigatoka (Mycosphaerella fijiensis, Mycosphaerella musicola); diseases of lentil: Ascochyta (Ascochyta lentis); Chickpea diseases: Ascochyta (Ascochyta rabiei); Bell pepper diseases: Anthracnose (Colletotrichum scovillei); Mango diseases: Anthracnose (Colletotrichum acutatum); Sweet potato diseases: Root rot (Diaporthe destruens); Fruit tree diseases: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa); Post-harvest diseases of apples, pears, etc.: Mucor rot (Mucor piriformis); Seed diseases or diseases in the early stages of growth caused by species of the genera Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.; viral diseases: big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by the Polymyxa genus (e.g., Polymyxa betae and Polymyxa graminis);Diseases caused by bacteria: rice seedling bacterial blight (Burkholderia plantarii), rice inner glume browning disease (Pantoea ananatis), rice bacterial leaf blight (Xanthomonas oryzae pv. oryzae.), cucumber bacterial spot (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), corn Goss's wilt (Clavibacter michiganensis), Pierce's disease (Xylella fastidiosa) of grapes, olives, peaches, etc., and crown gall (Agrobacterium tumefaciens) of Rosaceae plants such as apples, peaches, and cherries. ;

[0029] The method for controlling plant diseases of the present invention includes, for example, treatments on plants such as foliage spray and seed disinfection; and treatments on plant cultivation areas such as soil treatment.

[0030] The amount of the compound of the present invention to be applied was 1000 m 2 When the compound of the present invention is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm (for example, 1,000 ppm), and granules, dusts and the like are usually applied as they are.

[0031] The composition of the present invention can be used as an agent for controlling plant diseases in agricultural lands such as fields, paddy fields, lawns, and orchards.

[0032] A composition that is one embodiment of the present invention is a composition (hereinafter referred to as Composition A) containing the compound of the present invention and at least one compound selected from the group consisting of metofluthrin and dimefluthrin. Metofluthrin and dimefluthrin can be used singly or in combination. Metofluthrin and dimefluthrin each have one or more stereoisomers, and the metofluthrin and dimefluthrin used in the present invention include stereoisomers and mixtures thereof. 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 dimefluthrin is not particularly limited, but may be 100,000:1 to 1:100,000, 50,000:1 to 1:50,000, or a range of 100,000:1 to 1:100,000, or 50,000:1 to 1:50,000, in terms of mass ratio (compound of the present invention:at least one compound selected from the group consisting of metofluthrin and dimefluthrin). , 10000:1 to 1:10000, 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 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, and the like.

[0033] Metofluthrin and dimefluthrin are known to each exhibit excellent control effects against harmful arthropods such as harmful insects and harmful mites. Therefore, composition A containing at least one compound selected from the group consisting of metofluthrin and dimefluthrin can also be expected to exhibit excellent control effects against harmful arthropods. Examples of harmful arthropods include the following. Hemiptera pests: planthoppers such as the small brown planthopper, the brown planthopper, and the white-backed planthopper; leafhoppers such as the green rice leafhopper and the Taiwanese green rice leafhopper; aphids, stink bugs, whiteflies, scale insects, earwigs, psyllids, etc.; Lepidoptera pests: moths such as the rice stem borer, the rice leaf borer, and the Indian meal moth; cutworms such as the common cutworm, the armyworm, and the armyworm; white butterflies such as the cabbage white butterfly; tortrix moths such as the smaller tea tortrix; fruit moths, leafminers, tussock moths, grasshoppers, Agrotis spp. such as the turnip cutworm and the black cutworm; Helicoverpa pests Heliothis spp.) pests of the genus Heliothis (Heliothis spp.), diamondback moth, skipper butterfly, bur moth, bur moth, etc.; Diptera pests: Culex mosquitoes such as Culex tritaeniorhynchus, Aedes mosquitoes such as Aedes aegypti and Aedes albopictus, Anopheles mosquitoes such as Anopheles sinensis, chironomids, house flies such as Musca domestica and Musca domestica, blow flies, flesh flies, seed flies, little house flies, onion flies, fruit flies, Drosophila, moth flies, horseflies, black flies, stable flies, etc.; Coleoptera pests: corn rootworms such as western corn rootworm and southern corn rootworm, scarab beetles such as cupre beetle and dung beetle, weevils such as rice weevils, rice water weevils, boll weevils, and azuki bean weevils, mealworm beetles such as brown mealworm and red flour beetle, leaf beetles such as rice leaf beetles, striped flea beetles, and cucumber beetles, beetles, Epilachna spp. such as 20-spotted ladybird beetles, flat-headed beetles, long-horn beetles, long-horn beetles, and blue-leaf rove beetles; Dictyoptera pests: German cockroach, Smoked cockroach, American cockroach, Brown cockroach, Oriental cockroach, etc.;Thysanoptera pests: Thrips palmi, occidental thrips, flower thrips, etc.; Hymenoptera pests: ants, hornets, ant wasps, sawflies such as turnip sawflies, etc.; Orthoptera pests: mole crickets, grasshoppers, etc.; Cryptoptera pests: human fleas, cat fleas, etc.; Phthiraptera pests: human lice, pubic lice, etc.; Isoptera pests: Reticulitermes speratus, Coptotermes formosanus, etc.; Indoor dust mites: Dermatophagoides such as Dermatophagoides farinae and Dermatophagoides pteronyssinus, astigmatids such as Tyrophagus putrescentiae and Aspergillus oryzae, flesh mites such as Glycanthropus dust mite, Glycanthropus domesticus, and Glycanthropus gracilis, chiggers such as Cheyletidae and Cheyletidae, dust mites, Sarcophagidae, house mites, spider mites, ixodid mites such as Haemaphysalis longicornis, twospotted spider mites, Kanzawa spider mites, citrus red mite, European red mite, etc. Harmful arthropods may be those with reduced sensitivity to insecticides, acaricides, etc., or which have developed resistance to such drugs.

[0034] The compound of the present invention or Composition A is usually used as a composition further containing an inert carrier (hereinafter referred to as Composition B). Composition B is usually prepared by mixing the compound of the present invention or Composition A with a liquid carrier, a surfactant, etc., and, if necessary, adding formulation adjuvants such as a thickener, a binder, a dispersant, a stabilizer, and a gas, and can be used in the form of oil solutions, emulsifiable concentrates, wettable powders, flowable formulations (water suspensions, water emulsions, etc.), dusts, granules, aerosol formulations (direct spray type, space spray type, metered spray type, one-push type, total spray type, intermittent spray type, etc.), sprays, electric sprays (ultrasonic vibration type, electrostatic spray type, etc.), heated evaporative formulations (incense sticks, electric mats, absorbent wick-type heated evaporative formulations, etc.), non-heated evaporative formulations (resin evaporative formulations, impregnated paper evaporative formulations, net formulations, etc.), aerosols (fogging, etc.), ULV (Ultra Low Volume) formulations, etc. A formulation that is one embodiment of the present invention is a formulation selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated evaporative formulations, non-heated evaporative formulations, mist formulations, and ULV formulations, which contain the compound of the present invention or Composition A. These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention or Composition A relative to the total weight of the formulation.

[0035] Examples of liquid carriers 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, trichloromethane, carbon tetrachloride, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), mineral oils (kerosene, heating oil, diesel, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.). A composition that is 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. Also, a formulation that is one embodiment of the present invention is a formulation that contains the composition and is selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heat-transferables, and ULV formulations.

[0036] Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.A composition according to 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 sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.Furthermore, a formulation according to one embodiment of the present invention is a formulation selected from the group consisting of emulsions, flowables, and heat-transposable formulations containing the composition.

[0037] Examples of thickeners include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.). A composition according to one embodiment of the present invention contains 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. A formulation according to one embodiment of the present invention is a flowable preparation containing the composition.

[0038] Examples of antioxidants 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). A composition that is 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. A formulation that is one embodiment of the present invention is a formulation that contains the composition and is selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated evaporative formulations, non-heated evaporative formulations, aerosols, and ULV formulations.

[0039] A composition that is one embodiment of the present invention is a composition in which the compound of the present invention or Composition A is supported on a plant powder (wood flour, oat flour, etc.). The plant powder may be used by mixing the plant powder with a binder (tab flour, starch, gluten, etc.). A formulation that is one embodiment of the present invention is a heat-transmittable agent containing the composition. A composition that is yet another embodiment of the present invention is a composition containing the compound of the present invention or Composition A and a binder. A formulation that is one embodiment of the present invention is a heat-transmittable agent containing the composition.

[0040] A composition according to one embodiment of the present invention is a composition comprising the compound of the present invention or composition A supported on one or more substrates selected from the group consisting of cotton linters and pulp. Specific examples of the substrate include cotton linters solidified into a plate shape and a fiber mixture of cotton linters and pulp solidified into a plate shape. A formulation according to one embodiment of the present invention is a heat-transmissible agent containing the composition.

[0041] A composition according to one 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 or paper. A formulation according to one embodiment of the present invention is a non-heated vaporizable agent containing the composition. 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 copolymer; ethylene-methacrylic acid ester copolymers such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer; ethylene-acrylic acid ester copolymers such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resins such as propylene polymers and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene, acrylonitrile-styrene resins; acrylic acid copolymers such as acrylic acid copolymers; and acrylic acid copolymers. Examples of suitable resins include styrene-based elastomers such as thiazolinone-butadiene-styrene resin, styrene-conjugated diene copolymer, and hydrogenated styrene-conjugated diene block copolymer; fluororesins; 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 polycyclohexylene dimethylene terephthalate; polycarbonate, polyacetal, polyacrylsulfone, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, and polyurethane. These resins may be used alone or in combination. If necessary, plasticizers such as phthalates (e.g., dimethyl phthalate, dioctyl phthalate), adipates, and stearic acid may be added to these resins. Examples of suitable paper include filter paper and Japanese paper. A composition that is 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.A composition that is yet another embodiment of the present invention is a composition in which the compound of the present invention or Composition A is supported on paper.

[0042] The present invention will be explained in more detail below with reference to Production Examples, Reference Production Examples, Test Examples, etc., but the present invention is not limited to these examples.

[0043] First, examples of the preparation of the compounds of the present invention will be shown.

[0044] Reference Production Example 1: To a mixture of 2.0 g of (S)-5,5-dimethyl-4-(1-propenyl)dihydrofuran-2(3H)-one (prepared according to the method described in J. Chem. Soc. Perkin trans 1,2,196 (1977)) and 13 mL of ethanol, 13 mL of 1N aqueous potassium hydroxide solution was added and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure to give 1.0 g of potassium (S)-3-(2-hydroxypropan-2-yl)-4-hexenoate represented by the following formula: 1 H-NMR (DMSO-d6) δ: 5.35 (2H, m), 3.35(1H, br s), 2.55 (1H, m), 2.14 (2H, m), 1.58 (3H, s), 1.02 (3H, s), 0.93 (3H, s).

[0045] Production Example 1: To a mixture of 2.38 g of potassium (S)-3-(2-hydroxypropan-2-yl)-4-hexenoate and 13 mL of dimethylformamide, 3.25 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl bromide was added, and the mixture was stirred at room temperature for 2 hours. The resulting mixture was diluted with tert-butyl methyl ether, added to water, and the layers were separated. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 4.1 g of a compound represented by the following formula (II-1) (referred to as Compound 1 of the Present Invention).

[0046] Compound 1 of the present invention 1 The H-NMR data is shown below. 1H-NMR (CDCl3) δ: 5.65 (1H, m), 5.17 (1H, m), 5.19 (2H, s), 4.58 (2H, s), 3.40 (3H, s), 2.98 (1H, m), 2.70 (1H, m), 2.21 (1H, m), 1.62 (3H, s), 1.19 (3H, s), 1.16 (3H, s).

[0047] Production Example 2: To a mixture of 0.97 g of Compound 1 of the present invention and 12 mL of pyridine, 0.59 g of phosphorus oxychloride was added and stirred at room temperature for 21 hours. The resulting mixture was diluted with tert-butyl methyl ether and added to water, followed by separation of the layers. The resulting organic layer was washed successively with 5% hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=40:1) to afford 0.59 g of a compound represented by the following formula (II-2) (referred to as Compound 2 of the present invention).

[0048] Compound 2 of the present invention 1 The H-NMR data is shown below. 1 H-NMR (CDCl3) δ: 5.52 (1H, m), 5.21 (2H, s), 5.20 (1H, m), 4.71 (2H, s), 4.58 (2H, s), 3.40 (3H, s), 3.52 (1H, m), 2.59 (1H, m), 2.40 (1H, m), 1.74 (3H, s), 1.64 (3H, s).

[0049] Next, the efficacy of the compounds of the present invention against plant diseases will be demonstrated by test examples. DMSO means dimethyl sulfoxide. In test examples 1 to 3, the untreated group refers to a test group conducted under the same conditions as those described in the test examples, except that DMSO was dispensed instead of the DMSO dilution containing the compounds of the present invention.

[0050] Test Example 1: Control test against barley scald fungus (Rhynchosporium secalis) Compound 1 or 2 of the present invention was diluted with DMSO to contain 66.7 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of barley scald fungus was dispensed. The plate was cultured at 18°C ​​for 7 days to allow the barley scald fungus to grow. The absorbance at 550 nm of each well of the titer plate was measured, and this value was used as the growth rate of the barley scald fungus. As a result, the growth rate in the plots treated with Compound 1 or 2 of the present invention was 5% or less of the growth rate in the untreated plot.

[0051] Test Example 2: Control test against peach scab fungus (Cladosporium carpophilum) Compound 1 or 2 of the present invention was diluted with DMSO to contain 66.7 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells), followed by 150 μL of YB liquid medium previously inoculated with spores of peach scab fungus. The plate was cultured at 18° C. for 5 days to allow the peach scab fungus to grow, after which the absorbance at 550 nm of each well of the titer plate was measured, and this value was taken as the growth rate of the peach scab fungus. As a result, the growth rate in the plots treated with Compound 1 or 2 of the present invention was 5% or less of the growth rate in the untreated plot.

[0052] Test Example 3: Control test against wheat leaf spot fungus (Septoria tritici) Compound 2 of the present invention was diluted with DMSO to contain 66.7 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of Septoria tritici was dispensed. The plate was incubated at 18°C ​​for 5 days to allow the wheat leaf spot fungus to grow. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of the wheat leaf spot fungus. As a result, the growth rate in the treatment area with Compound 2 of the present invention was 5% or less of that in the untreated area.

[0053] The compound of the present invention exhibits excellent control effects against plant diseases.

Claims

1. Formula (I): (wherein R represents a 2-hydroxypropan-2-yl group or a 1-propen-2-yl group.) 2. The compound of formula (I) is a compound of formula (II):

2. The compound according to claim 1, which is a compound represented by the formula: wherein R represents a 2-hydroxypropan-2-yl group or a 1-propen-2-yl group.

3. The compound of claim 1, wherein R is a 2-hydroxypropan-2-yl group.

4. The compound of claim 2, wherein R is a 2-hydroxypropan-2-yl group.

5. The compound of claim 1, wherein R is a 1-propen-2-yl group.

6. The compound of claim 2, wherein R is a 1-propen-2-yl group.

7. A composition comprising a compound according to any one of claims 1 to 6 and an inert carrier.

8. A method for controlling plant diseases, which comprises applying an effective amount of the compound according to any one of claims 1 to 6 to plants or soil.

9. A composition comprising the compound according to any one of claims 1 to 6 and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin.

10. A composition comprising the compound according to any one of claims 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.

11. A composition comprising the composition of claim 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.

12. A composition containing the compound according to any one of claims 1 to 6 and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.

13. A composition comprising the composition according to claim 9 and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.

14. A composition comprising the compound according to any one of claims 1 to 6 and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers.

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

16. A composition containing the compound according to any one of claims 1 to 6 and one or more antioxidants selected from the group consisting of BHT (2,6-di-t-butyl-4-methylphenol) and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).

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

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

19. A composition in which the composition according to claim 9 is supported on a plant powder.

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

21. A composition comprising the composition of claim 9 and a binder.

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

23. A composition comprising the composition according to claim 9 supported on one or more substrates selected from the group consisting of cotton linters and pulp.

24. A composition comprising the compound according to any one of claims 1 to 6 supported on a thermoplastic resin or paper.

25. A composition in which the composition according to claim 9 is supported on a thermoplastic resin or paper.

26. A preparation selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated vaporization preparations, non-heated vaporization preparations, aerosols, and ULV preparations, which contains the compound according to any one of claims 1 to 6.

27. A formulation containing the composition of claim 9, selected from the group consisting of oil solutions, emulsions, flowables, aerosols, thermal evaporatives, non-thermal evaporatives, mist solutions, and ULV solutions.