WO2017169893A1 - Oxadiazole compound and use thereof - Google Patents

Abstract

An oxadiazole compound represented by formula (I) [wherein R¹ represents a halogen atom or a C1-C2 alkyl group; n represents an integer of 0 to 2; and R² represents a C2-C6 alkyl group or a C3-C4 alkenyl group] has an excellent controlling effect against plant diseases.

Description

Oxadiazole compounds and uses thereof

The present invention relates to an oxadiazole compound and its use.

Conventionally, various compounds have been developed to control plant diseases (see Patent Document 1).

JP 63-162680 A

An object of the present invention is to provide a compound having an excellent control effect against plant diseases.

As a result of studies to find a compound having an excellent control effect against plant diseases, the present inventor has found that the compound represented by the following formula (I) has an excellent control effect against plant diseases.
That is, the present invention is as follows.
[1] Formula (I)

[Where,
R ¹ represents a halogen atom or a C1-C2 alkyl group,
n represents an integer of 0-2 (when n is 2, two R ¹ may be the same or different),
R ² represents a C2-C6 alkyl group or a C3-C4 alkenyl group. ]
An oxadiazole compound represented by the following (hereinafter referred to as the present compound).
[2] The compound according to [1], wherein n is 0 and R ² is a C2-C5 alkyl group or a 2-propenyl group.
[3] A plant disease control agent containing the compound according to either [1] or [2] (hereinafter referred to as the present invention control agent).
[4] A method for controlling plant diseases by treating a plant or soil with an effective amount of the compound according to [1] or [2].
[5] Use of the compound according to either [1] or [2] for controlling plant diseases.

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

The substituents in this specification will be described.
In this specification, the expression “CX-CY” means that the number of carbon atoms is X to Y. For example, the notation “C2-C6” means 2 to 6 carbon atoms.

“Halogen atom” represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
Examples of the “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, tert-butyl group, A pentyl group and a hexyl group are mentioned.
Examples of the “alkenyl group” include 2-propenyl group, 2-butenyl group and 3-butenyl group.

Examples of the compound of the present invention include the following compounds.

An oxadiazole compound in which n is 0 or 1 in the compound of the present invention.
An oxadiazole compound in which n is 0 in the compound of the present invention.
An oxadiazole compound in which R ² is a C2-C6 alkyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a C3-C4 alkenyl group in the compound of the present invention.
An oxadiazole compound in which R ² is an ethyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a propyl group in the compound of the present invention.
An oxadiazole compound in which R ² is an isopropyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a butyl group in the compound of the present invention.
An oxadiazole compound wherein R ² is a sec-butyl group in the compound of the present invention.
An oxadiazole compound in which R ² is an isobutyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a tert-butyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a pentyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a 1-methylbutyl group in the compound of the present invention.
An oxadiazole compound in which R ² is an isopentyl group in the compound of the present invention.
The oxadiazole compound whose R < ² > is a neopentyl group in this invention compound.
The oxadiazole compound whose R < ² > is a hexyl group in this invention compound.
An oxadiazole compound in which R ² is a 2-propenyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a 2-butenyl group in the compound of the present invention.
An oxadiazole compound in which R ² is a 3-butenyl group in the compound of the present invention.
An oxadiazole compound wherein n is 0 or 1 and R ² is an ethyl group or a propyl group in the compound of the present invention.
An oxadiazole compound in which n is 0 and R ² is an ethyl group or a propyl group in the compound of the present invention.
An oxadiazole compound in which n is 0 and R ² is an ethyl group in the compound of the present invention.
An oxadiazole compound in which n is 0 and R ² is a propyl group in the compound of the present invention.

An oxadiazole compound in which n is 0 or 1, and R ² is an ethyl group, a propyl group or an isopropyl group in the compound of the present invention.
An oxadiazole compound in which n is 0 and R ² is an ethyl group, a propyl group or an isopropyl group in the compound of the present invention.
An oxadiazole compound in which n is 0 or 1 and R ² is an isopropyl group in the compound of the present invention.
An oxadiazole compound wherein n is 1 and R ² is an isopropyl group in the compound of the present invention.
An oxadiazole compound in which n is 0 and R ² is an isopropyl group in the compound of the present invention.

Next, a method for producing the compound of the present invention will be described.

The compound of the present invention can be produced, for example, by the following production method.

Manufacturing method A
The compound of the present invention comprises a compound represented by formula (A1) (hereinafter referred to as compound (A1)) and a compound represented by formula (A2) (hereinafter referred to as compound (A2)) in the presence of a base. It can manufacture by making it react.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as hexane, cyclohexane and toluene, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as chloroform and chlorobenzene, amides such as dimethylformamide, and ethyl acetate. And the like, sulfoxides such as dimethyl sulfoxide, nitriles such as acetonitrile and propionitrile, water, and mixtures thereof.
Compound (A2) may be in the form of a salt. Examples of the salt of compound (A2) include hydrochloride or sulfate.
Examples of the base used in the reaction include organic bases such as diisopropylethylamine and pyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and hydrogen carbonate. Examples thereof include alkali metal hydrogen carbonates such as sodium.
In the reaction, with respect to 1 mol of compound (A1), compound (A2) is usually used at a ratio of 1 to 10 mol, and base is used at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of −20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as mixing the reaction mixture with water and extracting with an organic solvent, and drying and concentrating the organic layer.

Manufacturing method B
The compound of the present invention comprises a compound represented by formula (A3) (hereinafter referred to as compound (A3)) and a compound represented by formula (A4) (hereinafter referred to as compound (A4)) in the presence of a base. It can manufacture by making it react.

[The symbols in the formula have the same meaning as described above. ]
The reaction can be carried out according to the method described in Production Example 1, using compound (A3) instead of compound (A1) and compound (A4) instead of compound (A2).
Compound (A3) and compound (A4) are known compounds or can be produced according to known methods (for example, the method described in JP-A No. 63-162680).

Manufacturing method C
Compound (A1) can be produced by reacting a compound represented by formula (A3) (hereinafter referred to as compound (A3)) with phosgene, diphosgene or triphosgene in the presence of a base.

[Wherein the symbols have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as hexane, cyclohexane and toluene, ethers such as diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as chloroform and chlorobenzene, amides such as dimethylformamide, and ethyl acetate. And the like, sulfoxides such as dimethyl sulfoxide, nitriles such as acetonitrile and propionitrile, water, and mixtures thereof.
Examples of the base used in the reaction include organic bases such as diisopropylethylamine and pyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and hydrogen carbonate. Examples thereof include alkali metal hydrogen carbonates such as sodium.
In the reaction, with respect to 1 mol of compound (A1), phosgene is usually used at a ratio of 1 to 10 mol, and base is used at a ratio of 1 to 10 mol.
In the reaction, with respect to 1 mol of the compound (A1), diphosgene is usually used in a proportion of 0.5 to 5 mol, and the base is used in a proportion of 1 to 10 mol.
In the reaction, with respect to 1 mol of compound (A1), triphosgene is usually used in a proportion of 0.3 to 3 mol, and the base is used in a proportion of 1 to 10 mol.
The reaction temperature is usually in the range of −20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.

As a form in which the compound of the present invention is used, the compound of the present invention may be used alone. Usually, the compound of the present invention is mixed with a solid carrier, a liquid carrier, and / or a surfactant, and if necessary, a fixing agent. , Dispersants, stabilizers and other formulation aids added, wettable powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol It is used in the form of pharmaceutical preparations and microcapsules. These preparations contain the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.

Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fubasamic clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate) and the like.
Examples of the liquid carrier include water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (For example, hexane, kerosene), esters, nitriles, ethers, amides, and halogenated hydrocarbons.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyvalent Examples include alcohol esters and sugar alcohol derivatives.

Other formulation adjuvants include, for example, fixing agents, dispersants, and stabilizers. Specifically, casein, gelatin, polysaccharides (eg, starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, Bentonite, sugars, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol) ), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or ester thereof, and the like.

The compound of the present invention may be used by mixing with various oils such as mineral oil and vegetable oil, or surfactants. Oils that can be specifically mixed and used as surfactants are Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark) , Nufilm (registered trademark), Emulator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N ( Recorded trademark), BANOLE (registered trademark), and the like.

The compound of the present invention is applied as the control agent of the present invention. The method of the present invention is not particularly limited as long as the control agent of the present invention can be practically applied, but for example, treatment to plants such as foliage spraying, soil treatment, etc. Treatment, seed treatment such as seed disinfection, treatment of harmful arthropods, and the like.
In the control method of the present invention, the treatment amount of the compound of the present invention depends on the type of plant to be treated, the type and occurrence frequency of plant diseases to be controlled, formulation form, treatment time, treatment method, treatment place, weather conditions, etc. The compound of the present invention is usually 1 to 500 g per 1000 m ² when it is treated on the foliage of the plant or on the soil where the plant is grown.
Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0005 to 2% by weight. Powders, granules, etc. are usually processed without dilution.

The compound of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards. The compound of the present invention can control diseases of the cultivated land in the cultivated lands where the “plants” and the like listed below are cultivated. Moreover, this invention compound can control the harmful arthropod of the said agricultural field.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc., vegetables; solanaceous vegetables (eggplant, tomato, pepper , Peppers, potatoes, etc.), cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, cold rabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower -, Etc.), Asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), Liliaceae vegetables (green onion, onion, garlic, asparagus), Aceraceae vegetables (carrot, parsley, celery, American redfish, etc.) , Red vegetables (spinach, chard, etc.), perilla vegetables (perilla, mint, basil) ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prune, etc.), citrus (satsuma mandarin, orange, lemon, lime) , Grapefruit, etc.), nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry) -Grapes, oysters, olives, loquat, bananas, coffee, dates, coconuts, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, tsuga, rat, Pine, spruce, yew).

The above “plants” include genetically modified crops.

Examples of plant diseases that can be controlled by the compound of the present invention include plant pathogens such as filamentous fungi and bacteria, and specific examples include, but are not limited to, the following.

Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew (Blumeria) graminis), red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), red snow rot (Microdochium nivale) , Microdochium majus), Snow rot microbe nuclei (Typhula incarnata, Typhula ishikariensis), Bare smut (Ustilago tritici), pine scab (Tilletia caries, Tilletia controversa), Eye disease (Pseudocercosporella herpotrichoides), Leaf Septoria tritici), blight disease (Stagonospora nodorum), macular disease (Pyrenophora tritici-repentis), Rhizoctonia solani, blight disease (Gaeuman) nomyces graminis); barley powdery mildew (Blumeria graminis), red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust Puccinia hordei), scab disease (Puccinia hordei), naked scab disease (Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy disease (Pyrenophora graminea), Ramallaria leaf spot disease (Ramularia collo-cygni), Rhizoctonia solani (Rhizoctonia solani); Corn rust (Puccinia sorghi), Southern rust (Puccinia polysora), Soot disease (Setosphaeria turcica), Tropical Sexual rust (Physopella zeae), sesame leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot disease (Cercospora zeae-maydis), Spot disease (Kabatiella zeae), Faeosphaeria reef spot disease (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpella macrospora, Stokelot disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis); Diseases (Colletotrichum gossypii), mildew (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), Black root rot disease (Thielaviopsis basicola) caused by Thielaviopsis spp .; coffee rust (Hemileia vastatrix), leaf spot disease (Cercospora coffeicola); Sclerotinia sclerotiorum, black spot disease (Alternaria brassicae), root rot disease (Phoma lingam); sugarcane rust disease (Puccinia melanocephela, Puccinia kuehnii), smut disease (Ustilago scitaminea) Sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Citrus sunspot (Diaporthe citri) , Common scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, Penicillium italicum), plague (Phytophthora parasitica, Phytophthora citrophthora); apple monilia (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podosera) leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthracnose (Glomerella cingulata), brown spot disease (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), plague (Phytophtora cactorum); Pear black spot disease (Venturia nashicola, Venturia pirina), black spot disease (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); peach asteroid disease (Monilinia fructicola), black star disease (Cladosporium carpophilum), fomosis rot (Phomopsis sp.); Grapes black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae); cucurbit anthracnose (Colletotrichum lagenarium) ), Powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.), Seedling Standing disease (Pythium sp.); Tomato ring-rot (Alternaria solani), leaf mold (Cladosporium fulvum), mold mold (Pseudocercospora fuligena), plague (Phytophthora infestans), powdery mildew (Leveillula taurica); eggplant Brown spot disease (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); cruciferous vegetable black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae), clubroot disease (Plasmodiophora brassicae), Downy mildew (Peronospora parasitica); green onion rust (Puccinia allii); soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae), rust (Phakopsora pachyrhizi) , Brown ring disease (Corynespora cassiicola), anthrax (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown leaf disease (Septoria glycines), spot disease (Cercospora sojina), sclerotia (Sclerotinia sclerotiorum) , Powdery mildew (Microsphaera diffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme); kidney bean sclerotia (Sclerotinia sclerotiorum), rust (Uromyces appendiculatus), horn Spot disease (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum); groundnut black rot (Cercospora personata), brown spot (Cercospora arachidicola), white silkworm (Sclerotium rolfsii); Powdery mildew (Erysiphe pisi); Potato summer plague (Alternaria solani), plague (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. Sp. Subterranea), half-body wilt Diseases (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens); Strawberry powdery mildew (Sphaerotheca humuli); Chamochi rice rot (Exobasidium reticulatum), White spot disease (Elsinoe leucospila), Ring spot disease (Pestalotiopsis sp.) Anthracnose (Colletotrichum theae-sinensis); tobacco red star disease (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae); brown spot of sugar beet (Cercospora beticola) Leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides), rust (Uromyces betae); rose scab (Diplocarpon rosae), Powdery mildew (Sphaerotheca pannosa); chrysanthemum leaf spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); allii), Bacterial rot (Botrytis squamosa); Gray rot of various crops (Botrytis cinerea), Mycorrhizal sclerosis (Sclerotinia sclerotiorum); Japanese radish black spot (Alternaria brassicicola); homoeocarpa), brown patch disease and Rhizoctonia solani of shiba; and sigatoka disease of banana (Mycosphaerella fijiensis, Mycosphaerella musicola).
Seed disease or early growth of various crops caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia Disease. Viral diseases of various crops mediated by Polymyxa genus or Olpidium genus.
Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citri); carotovora) etc.

Examples of harmful arthropods that can be controlled by the compounds of the present invention include the following.
Hemiptera: Japanese brown planthopper (Laodelphax striatellus), Japanese brown planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), yellow-spotted plant (Javesella pellucida), black-tailed squid (Delphacidae); Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Eki ca ), Corn Leaf Hopper (Dalbulus maidis), Cofana spectra, etc., Cicadellidae; Mahanarva posticata, Mahanarva fimbriolata, etc., Cercopidae; Aphis fabae, soybean aphids (Aphis glycines), cotton aphids (Aphis gossypii), European apple aphids (Aphis pomi), snowy aphids (Aphis spiraecola), peach aphids (Myzus persicae), wheat arasi , Radish aphids (Brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), black radish aphids (Lipaphis erysimi), tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), aphids Aphids (Rhopalosiphum padi), corn aphids (Rhopalosiphum maidis), citrus aphids (Toxoptera citricida), peach beetles (Hyalopterus pruni), hyena aphids (Melanaphi) s sacchari), Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, etc. (Aphididae); Leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae) and other aphids (Phylloxeridae); ; Scotinophara lurida, Malayan rice black bug (Scotinophara coarctata), Nezara antennata, Eysarcoris aeneus, Eysarcoris ysori village Eysarcoris annamita, Hailyomorpha halys, Southern stink bug (Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalchel pugnax Pentatomidae); Burrower brown bug (Scaptocoris castanea) and other hornworms (Cydnidae); ); Coleus punctiger, Leptoglossus australis, etc. (Coreidae); Blissus leucopterus) (Lygaeidae); Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, ario des riode (Rygus) , Tobacco whitefly (Bemisia tabaci), Daleurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Peleius eleyae, etc. (Abgrallaspis cyanophylli), Aonidiella aurantii, Nasimaru scale (Diaspidiotus perniciosus), Scarab scale (Pseudaulacaspis pentagona), Bamboo scale (Unaspis yanonensis), Diaspididae such as Unaspis citri; Coccidae such as Ceroplastes rubens; Icerya purchasi; Icerya purchasi; Icerya seychellarum Scales (Margarodidae); Phenacoccus solani, Phenacoccus solenopsis, Pteracoccus kraunhiae, Pseudococcus comstockicus, trichomec (Pseudococcus calceolariae), Pseudodococcus longispinus, Tattlemy Lee Bug (Brevennia rehi), etc. (Pseudococcidae); Diaphorina citri, Cigarette Whale (Tr ioza erytreae), Pepylthalidae (Cacopsylla pyrisuga), Pepylthiaceae (Psylliduch), Pear psylla (Cacopsylla pyricola) Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, etc., Gingidae (Tingidae); .

Lepidoptera: Green moth (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Itteno eel moth (Scirpophaga incertulas), Rupela albina medina, Hacasino maiga (Marasmia exigua), cotton moth (Notarcha derogata), yellow corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), yellow moth (Hellula undalis), monk black moth terrel Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. (Cambidae); tera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritae, ranga pods Spodoptera exempta, Tamanayaga (Agrotis ipsilon), Tamanaginawaba (Autographa nigrisigna), Echinocera (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia thisppa, Trichoplusia spp Genus (Heliothis spp.), Helicoverpa armigera, Helicoverpa zea and other Helicobelpa species (Helicoverpa spp.), Velvetbean caterpillar (Anticarsia gemmatalis), CottonHleafworm (Alabama argillav), Noctuidae such as ine borer (Hydraecia immanis); Pieridae such as Pieris rapae; Grapholita molesta, Grapholita dimorpha, glycine Matsumuraeses azukivora, Adoxophyes orana fasciata, Chanocok's leaflet (Adoxophyes honmai), Chamonaki (Homona magnanima), Midarekamon leaflet (Archips fuscocupreanus), Kodlinga ella, Mocha schistaceana), Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana) and other species of Tortricidae (Tortricidae); Carposin e (Carposina sasakii), etc. Carposinidae; Coffee Leaf miner (Leucoptera coffeella), peach leaf moth (Lyonetia clerkella), winged leaf moth (Lyonetia prunifoliella), etc. Lymantriidae such as Euproctis spp. Such as Eumantis genus (Lymantria spp.), Euproctis pseudoconspersa; Plutellidae such as Plutella xylostella; Plutellidae such as Plumellidae; Helicopteraceae (Gelchiidae) such as Helcystogramma triannulella, Pectinophora gossypiella, potato moth (Phthorimaea operculella); Castnii family (Castnii) dae); Arcticidae (Cossus insularis), etc. (Cossidae); Ascotis selenaria, etc. Staphmopodidae, etc .; Sphingidae, such as Acherontia lachesis; Ssiidae, such as Nokona feralis;

Thysanoptera: Citrus thrips (Frankliniella occidentalis), Thrips palmiet (Sriptos etbisiton) ), Thripidae such as Echinothrips americanus; Phthaothripripae such as Haplothrips aculeatus.

Diptera: Drosophila (Delia platura), onion flies (Delia antiqua), etc., Anthomyiidae; Tomato leafhopper (Liriomyza sativae), bean leafworm (Liriomyza trifolii), leafhopper (Chromatomyia horticola) and other leafworms (Agromyzidae); ), Eggplant fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quinzland fruit fly (Bactrocera tryoni), CeratitisCcapitata, etc. (Tephritidae); Hydrellia philippina, Hydrellia sasakii, and other species (Ephydridae); Drosophila suzukii, etc .; Drosophilidae Phoridae; Psychodidae such as Clogmia albipunctata; Spharidae such as Bradysia difformis; Mayetiola destructor; Cecidomyiidae, etc .; Diops macrophthalma, etc .; Diopsidae; Gillidae (Tipula aino), Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa), etc.

Coleoptera: Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cue Diabrotica balteata), Cucurbit tle Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Bark beetle (Oulema melanopus), potato beetle (Aulacophora femoralis), Phyllotreta bb Cabe black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Inedro beetle (Oulema oryzae), Grape colaspis (Colaspis brunnea) ), Corn flare beetle (Chaetocnema pulicaria), sweet potato beetle (Chaetocnema confinis), potato flare beetle (Epitrix cucumeris), rice beetle (Dicladispa armigera), southern corn leaf ), Chrysomelidae such as Epitrix hirtipennis; Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons), etc. Carabidae; , Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), Black marsh (Tomarus gibbosus), Holotrichiall Haga crinita) and other genus Phyllophaga genus (Phyllophaga spp.), Diloboderus usabderus genus Diloboderus genus (Diloboderus spp.) and other scarab beetles (Scarabaeidae); Eusces Sphenophorus venatus), Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus S subsignatus), Sugarcane weevil (Sphenophorus levis), Sabihyo weevil (Scepticus griseus) mis), Brazilian weevil (Zabrotes subfasciatus), pine beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus mourei, etc. ); Tribolium castaneum, Tribolium confusum, etc .; Tenebrionidae; Epilachna vigintioctopunctata, etc .; Bostrychidae; Leopardidae (Ptinidae); Anoplophora malasiaca, Migdolus fryanus, etc. , Melanotus legatus, Anchastus spp., Connoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., Etc. Elateridae; Staphylinidae such as Paederus fuscipes.

Orthoptera: Tosama locust (Locusta migratoria), Moroccan flying grasshopper (Dociostaurus maroccanus), Australian flying grasshopper (Chortoicetes terminifera), Red-spotted grasshopper (Nomadacris septemfasciata), Brown Locust ina Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoula femurrubrum) gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Cobainago (Oxya yezoensis), Red-tailed hawk (Oxya japonica), Grasshopper Locust (Patanga succincta), etc. rididae); Gryllotalpidae such as Gryllotalpa orientalis; Grylidae such as Acheta domestica; Gryllidae such as Teleogryllus emma;

Hymenoptera: bee (Athalia rosae), Japanese bee (Athalia japonica) and other bees (Tenthredinidae); fire ant (Solenopsis spp.), Brown leaf-cutting ant (Atta Department (Formicidae) etc.

Cockroaches (Blattodea): German cockroaches (Blattellidae) such as the German cockroach (Blattella germanica); Family (Blattidae); Yamato termite (Reticulitermes speratus), Japanese termite (Coptotermes formosanus), American ant termite (Incisitermes orminor), Great white termite (Cryptotermes domesticus), Thai one termite (Odontotermes マ ant hunter) (Glyptotermes satsumensis), Nakajima Termites (Glyptotermes nakajimai), Caterpillars (Glyptotermes fuscus), Termites (Hodotermopsis sjostedti), Coptotermes guangzhouen sis), Amite Termites (Reticulitermes amamianus), Miyatake Termites (Reticulitermes miyatakei), Camellia Termites (Reticulitermes kanmonensis), Takashi Termites (Nasutitermes takasagoensis), Nitobe Termites (Pericapritermes sharimuestermitermes) Termitidae, etc.

Hereinafter, the present invention will be specifically described with reference to production examples, formulation examples and test examples, but the present invention is not limited to these examples.

Production Example 1
To a mixture of 0.13 g of triphosgene and 10 mL of chloroform, 0.30 g of 3- (4-hydroxyphenyl) -5- (trifluoromethyl) -1,2,4-oxadiazole, 0.22 mL of diisopropylethylamine, and 10 mL of tetrahydrofuran Was added dropwise and stirred at room temperature for 1 hour. A mixture of ethylmethylamine 0.17 mL, diisopropylethylamine 0.33 mL, and chloroform 10 mL was added dropwise to the resulting mixture, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.28 g of the present compound 1 shown below.

The present compound 1:
¹ H-NMR (CDCl ₃ , 25 ° C) δ: 8.13 (2H, d), 7.31 (1H, d), 7.29 (1H, d), 3.50 (1H, q), 3.43 (1H, q), 3.10 ( 1.5H, s), 3.02 (1.5H, s), 1.27 (1.5H, t), 1.21 (1.5H, t).

The compounds produced according to the method described in Production Example 1 and their physical properties are shown below.
Formula (II)

Wherein R ³ is represented by the following:

Compound 2 of the present invention (R ³ : CH ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ , 25 ° C) δ: 8.12 (2H, d), 7.30 (1H, d), 7.28 (1H, d), 3.41 (1H, t), 3.34 (1H, t), 3.10 ( 1.5H, s), 3.02 (1.5H, s), 1.75-1.60 (2H, m), 0.99 (1.5H, t), 0.96 (1.5H, t, J = 7.5 Hz).
Compound 3 of the present invention (R ³ : CH ₂ CH ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ , 25 ° C) δ: 8.13 (2H, d), 7.31 (1H, d), 7.28 (1H, d), 3.45 (1H, t), 3.37 (1H, t), 3.10 ( 1.5H, s), 3.02 (1.5H, s), 1.69-1.56 (2H, m), 1.46-1.32 (2H, m), 0.99 (1.5H, t), 0.97 (1.5H, t).
Compound 4 of the present invention (R ³ : CH ₂ CH ₂ CH ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ , 25 ° C) δ: 8.13 (2H, d), 7.31 (1H, d), 7.28 (1H, d), 3.44 (1H, t), 3.36 (1H, t), 3.10 ( 1.5H, s), 3.02 (1.5H, s), 1.72-1.57 (2H, m), 1.43-1.27 (4H, m), 0.97-0.89 (3H, m).
Compound 5 of the present invention (R ³ : CH ₂ CH═CH ₂ ):
¹ H-NMR (CDCl ₃ , 25 ° C) δ: 8.13 (2H, d), 7.32 (1H, d), 7.29 (1H, d), 5.95-5.80 (1H, m), 5.30-5.23 (2H, m ), 4.08-3.97 (2H, m), 3.08 (1.5H, s), 3.02 (1.5H, s).
Compound 6 of the present invention (R ³ : CH (CH ₃ ) ₂ ):
¹ H-NMR (CDCl ₃ , 25 ° C) δ: 8.13 (2H, d), 7.34-7.27 (2H, m), 4.56-4.45 (1H, m), 2.95 (1.7H, s), 2.89 (1.3H , s), 1.26 (2.6H, d), 1.21 (3.4H, d).

The compounds A1 to A75 of the present invention shown below (hereinafter, the compounds A1 to A75 of the present invention are collectively referred to as the compound A of the present invention) can be produced according to the above production method.

A1: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl ethyl (methyl) carbamate, A2: 4- [5- (trifluoromethyl) -1,2 , 4-Oxadiazol-3-yl] phenyl propyl (methyl) carbamate, 3A3: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isopropyl (methyl) Carbamate, A4: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl butyl (methyl) carbamate, A5: 4- [5- (trifluoromethyl) -1 , 2,4-oxadiazol-3-yl] phenyl sec-butyl (methyl) carbamate, A6: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl Isobutyl (methyl) carbamate, A7: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl tert-butyl (methyl) carbamate, A8: 4- [5- (Trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl pentyl (methyl) carbamate, A9: 4- [5- (trifluoromethyl) -1,2,4-oxadiazole- 3-yl] phenyl 1-methylbutyl (methyl) carbamate, A10: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isopentyl (methyl) carbamate, A11: 4 -[5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl neopentyl (methyl) carbamate, A12: 4- [5- (trifluoromethyl) -1,2,4- Oxadiazol-3-yl] phenyl hexyl (methyl) carbamate, A13: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-propenyl (methyl) carbamate , A14: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-butenyl (methyl) carbamate, A15: 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 3-butenyl (methyl) carbamate, A16: 2-fluoro-4- [5- (trifluoro Methyl) -1,2,4-oxadiazol-3-yl] phenyl ethyl (methyl) carbamate, A17: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazole -3-yl] phenyl propyl (methyl) carbamate, A18: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isopropyl (methyl) carbamate, A19: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl butyl (methyl) carbamate, A20: 2-fluoro-4- [5- ( Trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl sec-butyl (methyl) carbamate, A21: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4 -Oxadi Zol-3-yl] phenyl isobutyl (methyl) carbamate, A22: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl tert-butyl (methyl ) Carbamate, A23: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl pentyl (methyl) carbamate, A24: 2-fluoro-4- [ 5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 1-methylbutyl (methyl) carbamate, A25: 2-fluoro-4- [5- (trifluoromethyl) -1, 2,4-oxadiazol-3-yl] phenyl isopentyl (methyl) carbamate, A26: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] Phenyl neopentyl (methyl) carbamate, A27: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl Xyl (methyl) carbamate, A28: 2-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-propenyl (methyl) carbamate, A29: 2- Fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-butenyl (methyl) carbamate, A30: 2-fluoro-4- [5- (trifluoro Methyl) -1,2,4-oxadiazol-3-yl] phenyl 3-butenyl (methyl) carbamate, A31: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxa Diazol-3-yl] phenyl ethyl (methyl) carbamate, A32: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl propyl (methyl) Carbamate, A33: 3-Fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isopropyl (methyl) carbamate, A34: 3-F Fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl butyl (methyl) carbamate, A35: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl sec-butyl (methyl) carbamate, A36: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazole -3-yl] phenyl isobutyl (methyl) carbamate, A37: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl tert-butyl (methyl) Carbamate, A38: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl pentyl (methyl) carbamate, A39: 3-fluoro-4- [5 -(Trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 1-methylbutyl (methyl) carbamate, A40: 3-Fluoro-4- [5- (trifluoromethyl ) -1,2,4-oxadiazol-3-yl] phenyl isopentyl (methyl) carbamate, A41: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazole- 3-yl] phenyl neopentyl (methyl) carbamate, A42: 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl hexyl (methyl) carbamate, A43 : 3-fluoro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-propenyl (methyl) carbamate, A44: 3-fluoro-4- [5- (Trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-butenyl (methyl) carbamate, A45: 3-fluoro-4- [5- (trifluoromethyl) -1,2, 4-oxadiazol-3-yl] phenyl 3-butenyl (methyl) carbamate, A46: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] F Nyl ethyl (methyl) carbamate, A47: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl propyl (methyl) carbamate, A48: 2-chloro -4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isopropyl (methyl) carbamate, A49: 2-chloro-4- [5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl butyl (methyl) carbamate, A50: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3- Yl] phenyl sec-butyl (methyl) carbamate, A51: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isobutyl (methyl) carbamate, A52 : 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl tert-butyl (methyl) carbamate, A53: 2-chloro -4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl pentyl (methyl) carbamate, A54: 2-chloro-4- [5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl] phenyl 1-methylbutyl (methyl) carbamate, A55: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazole- 3-yl] phenyl isopentyl (methyl) carbamate, A56: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl neopentyl (methyl) carbamate, A57 : 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl hexyl (methyl) carbamate, A58: 2-chloro-4- [5- (tri Fluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-propenyl (methyl) carbamate, A59: 2-chloro-4- [5- (trifluoromethyl) -1,2,4- Oxadiazo -3-yl] phenyl 2-butenyl (methyl) carbamate, A60: 2-chloro-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 3- Butenyl (methyl) carbamate, A61: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl ethyl (methyl) carbamate, A62: 2-methyl- 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl propyl (methyl) carbamate, A63: 2-methyl-4- [5- (trifluoromethyl) -1 , 2,4-oxadiazol-3-yl] phenyl isopropyl (methyl) carbamate, A64: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl ] Phenyl butyl (methyl) carbamate, A65: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl sec-butyl (methyl) carbamate, A66: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isobutyl (methyl) carbamate, A67: 2-methyl-4- [5- ( Trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl tert-butyl (methyl) carbamate, A68: 2-methyl-4- [5- (trifluoromethyl) -1,2,4 -Oxadiazol-3-yl] phenyl pentyl (methyl) carbamate, A69: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 1- Methylbutyl (methyl) carbamate, A70: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl isopentyl (methyl) carbamate, A71: 2-methyl- 4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl neopentyl (methyl) carbamate, A72: 2-methyl-4- [5- (trifluoromethyl) -1 , 2,4-oxadiazol-3-yl] phenyl hexyl (methyl) carbamate, メ ー ト A73: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl ] Phenyl 2-propenyl (methyl) carbamate, A74: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 2-butenyl (methyl) carbamate, A75: 2-methyl-4- [5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenyl 3-butenyl (methyl) carbamate.

The compound of the present invention can be used in combination or in combination with plant disease control agents such as fungicides, insecticides, acaricides, nematocides, plant growth regulators or synergists (hereinafter referred to as “this component”). it can. Below, the example of the combination of this invention compound and this component is described. For example, tebuconazole + SX means a combination of tebuconazole and SX. The abbreviation SX means any one compound selected from the compound A of the present invention. The numbers in parentheses represent CAS registration numbers.
Tebuconazole + SX, prothioconazole + SX, metconazole + SX, ipconazole + SX, triticonazole + SX, difenoconazole + SX, imazalil + SX triadimenol) + SX, tetraconazole + SX, flutriafol + SX, bromuconazole + SX, propiconazole + SX, mefentrifluconazole + SX, ipfentrifluconazole (SX) ipfentrifluconazole) + SX, epoxiconazole + SX, cyproconazole + SX, mandestrobin + SX, azoxystrobin + SX, pyraclostrobin + SX, trifloxystrobin ( trifloxystrobin) + SX, fluoxast Robin (fluoxastrobin) + SX, picoxystrobin (SX), fenamidone (fenamidone) + SX, dimoxystrobin (SX) + metominostrobin (SX), pyribencarb (SX), sedaxane (SX) Penflufen + SX, fluxapyroxad + SX, fluopyram + SX, benzovindiflupyr + SX, boscalid + SX, carboxin + SX, penthiopyrad + SX, flutolanil (flutolanil) + SX, bixafen + SX, pydiflumetofen + SX, 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole -4-carboxamide (1383809-87-7) + SX, N-cyclopropyl-3- (difluoromethyl) -5 Fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (1255734-28-1) + SX, 3-difluoromethyl-1-methyl-N- (1,1 , 3-Trimethylindan-4-yl) pyrazole-4-carboxamide (141573-94-6) + SX, 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4 -Yl] pyrazole-4-carboxamide (1352994-67-2) + SX, metalaxyl + SX, metalaxyl-M + SX, metrafenone + SX, cyflufenamid + SX, proquinazid + SX, 3-chloro-5-phenyl-6-methyl-4- (2,6-difluorophenyl) pyridazine (1358061-55-8) + SX, 1- (2-{[1- (4-chlorophenyl) -1H-pi Zol-3-yl] oxymethyl} -3-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (1472649-01-6) + SX, 4- (2-bromo-4-fluorophenyl) ) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, fenpicoxamid + SX, N '-( 2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, isotianil + SX, oxolinic acid + SX, ferimzone + SX , Phthalide + SX, kasugamycin + SX, tebufloquin + SX, quinofumelin + SX, fenpyrazamine + SX, procymidone + SX, fludioxonil xonil + SX, tolclofos-methyl + SX, thiabendazole + SX, ethaboxam + SX, picarbutrazox + SX, oxathiapiprolin + SX, iminoctadine tritate + SX, iminoctadine albesilate + SX, fenpropimorph + SX, fenpropidin + SX, spiroxamine + SX, chlorothalonil + SX, folpet + SX, captan ( captan + SX, thiram + SX, silthiofam + SX, mancozeb + SX, cartap + SX, clothianidin + SX, thiamethoxam + SX, imidacloprid + SX, thiacloprid + SX, thiacloprid + SX + SX, flupyradifurone + SX, Sulfoxaflor + SX, triflumezopyrim + SX, dicloromezotiaz + SX, beta-cyfluthrin + SX, tefluthrin + SX, fipronil + SX, chlorantraniliprolol (chlorantraniliprole) + SX, cyantraniliprole + SX, tetraniliprole + SX, thiodicarb + SX, carbofuran + SX, fluxametamide + SX, afoxolaner + SX, uralflner + SX, broflanilide + SX, abamectin + SX, fluensulfone + SX, fluazaindolizine + SX, tioxazafen + SX, (E) -N- {1-[(6-chloro Pyridin-3-yl) methyl] pyridine-2 (1H) Iridene} -2,2,2-trifluoroacetamide (1689566-03-7) + SX, Mycorrhizal Fungi + SX, Bacillus firmus + SX, Bacillus amyloliquefaciens (Bacillus) amyloliquefaciens) + SX, Pasteuria nishizawae + SX, Pasteuria penetrans + SX.

The ratio of the compound of the present invention to the active ingredient is not particularly limited, but the weight ratio (the compound of the present invention: the active ingredient) is, for example, 1000: 1 to 1: 1000, 500: 1 to 1: 500. 100: 1 to 1: 100, 50: 1 to 1:50, 20: 1 to 1:20, 10: 1 to 1:10, 3: 1 to 1: 3, 1: 1 to 1: 500, 1 1: 1 to 1: 100, 1: 1 to 1:50, 1: 1 to 1:20, and 1: 1 to 1:10.

By treating the compound of the present invention with a plant, improvement in seedling establishment rate, increase in the number of healthy leaves, increase in plant height, increase in plant weight, increase in leaf area, increase in the number or weight of seeds or fruits, number of flowers or number of fruits The effect of promoting the growth of the plant, such as an increase in plant weight and an increase in root growth, is obtained. In addition, by treating the compound of the present invention with a plant, tolerance to temperature stress such as high temperature stress or low temperature stress, moisture stress such as drought stress or excessive humidity stress, or abiotic stress such as salt stress is improved.

Next, formulation examples are shown. In the preparation examples, “part” means “part by weight”.

Formulation Example 1 A formulation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds A of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide.

Formulation Example 2 After mixing 20 parts of any one of the compounds A of the present invention and 1.5 parts of sorbitan trioleate with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and finely pulverizing by a wet pulverization method, Into this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to obtain a preparation.

Formulation Example 3 A formulation is obtained by thoroughly pulverizing and mixing 2 parts of any one compound of the present compound A, 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one of the compounds A of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 5 After thoroughly mixing 2 parts of any one of the compounds A of the present invention, 1 part of synthetic hydrous hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, add water and knead well The preparation is obtained by combining and granulating and drying.

Formulation Example 6 20 parts of any one compound of the present compound A; 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to make a total amount of 100 parts, and pulverized The preparation is obtained by processing using a machine.

Next, test examples show that the compounds of the present invention are useful for controlling plant diseases. The untreated section in Test Example 1 to Test Example 3 was performed under the same conditions as described in each test example, except that dimethyl sulfoxide was dispensed instead of the dimethyl sulfoxide diluted solution containing the compound of the present invention. Represents a test zone. The term “no treatment” in Test Example 4 to Test Example 10 indicates that the mixture of the preparation containing the compound of the present invention and water was not sprayed.

Test Example 1 Control Trial against Wheat Leaf Blight Fungus (Septoria tritici) After diluting the compound 1, 2, 3, 5 or 6 of the present invention with dimethyl sulfoxide so as to contain 1500 ppm and dispensing 1 μL into a titer plate (96 well) 150 μL of a potato broth liquid medium (PDB medium) previously inoculated with spores of wheat leaf blight fungus was dispensed. This plate was cultured at 18 ° C. for 5 days to grow wheat leaf blight fungi. Then, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of wheat leaf blight fungi. As a result, the degree of growth in the group treated with the present compound 1, 2, 3, 5 or 6 was 50% or less of the degree of growth in the untreated group.

Test Example 2 Control test against soybean anthracnose fungus (Colletotrichum truncatum) After diluting with dimethyl sulfoxide to contain 1500 ppm of the compound 1, 2, or 6 of the present invention and dispensing 1 μL into a titer plate (96-well), 150 μL of potato broth liquid medium (PDB medium) inoculated with spore was dispensed. This plate was cultured at 18 ° C. for 5 days to propagate soybean anthracnose fungi, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the degree of growth of soybean anthracnose fungus. As a result, the degree of growth in the group treated with the present compound 1, 2, or 6 was 50% or less of the degree of growth in the untreated group.

Test Example 3 Control Test against Tomato Leaf Mold Fungus (Cladosporium fulvum) After diluted with dimethyl sulfoxide so as to contain 1500 ppm of the present compound 3 or 6, 1 μL was dispensed in a titer plate (96 well), and then tomato leaf mold Potato broth liquid medium (PDB medium) inoculated with spores of (a QoI resistant strain whose base sequence has been mutated so that the amino acid residue at position 129 of cytochrome b is replaced with leucine from phenylalanine among genes encoding cytochrome b) ) Was dispensed in an amount of 150 μL. This plate was cultured at 18 ° C. for 5 days to proliferate the tomato leaf mold, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of the tomato leaf mold. As a result, the degree of growth in the group treated with the compound 3 or 6 of the present invention was 50% or less of the degree of growth in the untreated group.

Test Example 4 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and cultivated in a greenhouse for 20 days. Thereafter, the compound 1 or 2 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration is 500 ppm, and the mixture is sufficiently adhered to the leaf surface of the rice. The foliage was sprayed. After spraying, the rice is air-dried and left for 6 days in contact with a rice seedling (variety: Hinohikari) that has been treated with the rice blast fungus under a high humidity of 24 ° C in the daytime and 20 ° C in the nighttime. The lesion area was investigated. As a result, the lesion area in the rice treated with the present compound 1 or 2 was 30% or less of the lesion area in the untreated rice.

Test Example 5 Pyrephorophora teres control test A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was sown therein and cultivated in a greenhouse for 7 days. The compound 6 of the present invention formulated according to the method described in Formulation Example 6 was mixed with water so that the concentration became 500 ppm, and the mixture was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the barley. . After spraying, the barley was air-dried, and two days later, a water suspension of barley reticular fungus spores was spray-inoculated. After inoculation, the barley was placed under high humidity in a greenhouse at 23 ° C. during the daytime and 20 ° C. during the night for 3 days and then cultivated in the greenhouse for 7 days. As a result, the lesion area in the barley treated with Compound 6 of the present invention was 30% or less of the lesion area in the untreated barley.

Test Example 6 Control Test against Soybean Rust (Phakopsora pachyrhizi) A plastic pot is filled with soil, soy (variety: Kurosengoku) is sown there, grown in a greenhouse for 10 days, and water containing summer spores of soybean rust fungus The suspension was spray inoculated. After inoculation, the present compound 1 was formulated according to the method described in Formulation Example 6 after placing soybeans in a humid room at 23 ° C. in the daytime and 20 ° C. for 1 day in a humid room and then cultivating in the greenhouse for 2 days. 2, 3, 4, 5 or 6 was mixed with water so as to have a concentration of 200 ppm, and the mixture was sprayed with foliage so as to adhere well to the leaf surface of the soybean. After spraying, the soybeans were air-dried and cultivated in a greenhouse for 8 days, and then the lesion area was examined. As a result, the lesion area in the soybean treated with the present compound 1, 2, 3, 4, 5 or 6 was 30% or less of the lesion area in the untreated soybean.

Test Example 7 Control test against soybean rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and soybean (cultivar; Kurosengoku) was sown therein and allowed to grow in a greenhouse for 13 days. The compound 1, 2, 3, 4, 5 or 6 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 ppm, and the mixture is added to the soybean leaf surface. The foliage was sprayed so as to adhere well. After spraying, the soybean was air-dried, and after 4 days, a water suspension containing spores of soybean rust was spray-inoculated. After inoculation, the soybeans were placed in a humid room at 23 ° C. in the daytime and 20 ° C. for one day under high humidity, then cultivated in the greenhouse for 10 days, and then the lesion area was examined. As a result, the lesion area in the soybean treated with the present compound 1, 2, 3, 4, 5 or 6 was 30% or less of the lesion area in the untreated soybean.

Test Example 8 Control Trial against Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and then wheat (cultivar; Apogee) was sown therein and allowed to grow in a greenhouse for 10 days. The compound 1, 2, 4, 5 or 6 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 200 ppm, and the mixture is sufficiently applied to the leaf surface of the wheat. The foliage was sprayed to adhere. After spraying, the wheat was air-dried, and after 4 days, a water suspension containing spores of wheat leaf blight was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with the compound 1, 2, 4, 5 or 6 of the present invention was 10% or less of the lesion area in the untreated wheat.

Test Example 9 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, seeded with wheat (variety; Apogee), grown in a greenhouse for 10 days, and containing spores of wheat leaf blight fungus A water suspension was spray inoculated. After inoculation, the wheat is placed under high humidity at 18 ° C. for 3 days, and then the present compound 1, 2, 3, 4 or 5 formulated according to the method described in Formulation Example 6 is adjusted to a concentration of 200 ppm. The mixture was mixed with water, and the mixture was sprayed on the foliage so as to adhere well to the leaf surface of the wheat. After spraying, the wheat was air-dried and then placed under illumination for 11-14 days, after which the lesion area was examined. As a result, the lesion area in the wheat treated with the present compound 1, 2, 3, 4 or 5 was 30% or less of the lesion area in the untreated wheat.

Test Example 10 Control test against wheat red rust (Puccinia recondita) A plastic pot was stuffed with soil, sowed with wheat (cultivar: Shirogane), and grown in a greenhouse for 9 days. The compound 1, 2, or 5 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 200 ppm, and the mixture is sufficiently adhered to the leaf surface of the wheat. The foliage was sprayed. After spraying, the wheat was air-dried and cultivated at 20 ° C. under illumination for 5 days, and then sprinkled with spores of wheat red rust fungus. After inoculation, the wheat was placed in a dark and humid environment at 23 ° C. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination. As a result, the lesion area in the wheat treated with the compound 1, 2 or 5 of the present invention was 10% or less of the lesion area in the untreated wheat.

The compound of the present invention has a controlling effect against plant diseases and is useful as an active ingredient of a plant disease controlling agent.

Claims (5)

1. Formula (I)
   

   

   [Where,
   R ¹ represents a halogen atom or a C1-C2 alkyl group,
   n represents an integer of 0-2 (when n is 2, two R ¹ may be the same or different),
   R ² represents a C2-C6 alkyl group or a C3-C4 alkenyl group. ]
   An oxadiazole compound represented by the formula:
2. The compound according to claim 1, wherein n is 0 and R ² is a C2-C5 alkyl group or a 2-propenyl group.
3. The plant disease control agent containing the compound in any one of Claim 1 or Claim 2.
4. A method for controlling plant diseases by treating a plant or soil with an effective amount of the compound according to claim 1 or 2.
5. Use of the compound according to claim 1 or 2 for controlling plant diseases.