WO2017169893A1 - Composé oxadiazole et utilisation associée - Google Patents

Composé oxadiazole et utilisation associée Download PDF

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Publication number
WO2017169893A1
WO2017169893A1 PCT/JP2017/010881 JP2017010881W WO2017169893A1 WO 2017169893 A1 WO2017169893 A1 WO 2017169893A1 JP 2017010881 W JP2017010881 W JP 2017010881W WO 2017169893 A1 WO2017169893 A1 WO 2017169893A1
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Prior art keywords
compound
methyl
present
carbamate
trifluoromethyl
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English (en)
Japanese (ja)
Inventor
博人 玉島
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

Definitions

  • the present invention relates to an oxadiazole compound and its use.
  • Patent Document 1 Conventionally, various compounds have been developed to control plant diseases (see Patent Document 1).
  • An object of the present invention is to provide 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.
  • a plant disease control agent containing the compound according to either [1] or [2] (hereinafter referred to as the present invention control agent).
  • plant diseases can be controlled.
  • CX-CY means that the number of carbon atoms is X to Y.
  • C2-C6 means 2 to 6 carbon atoms.
  • Halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • alkyl group examples 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.
  • 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 R 2 is an ethyl 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 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.
  • the compound of the present invention can be produced, for example, by the following production method.
  • 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.
  • 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.
  • Compound (A2) may be in the form of a salt.
  • the salt of compound (A2) include hydrochloride or sulfate.
  • 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.
  • 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.
  • 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).
  • 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.
  • A3 a compound represented by formula (A3)
  • phosgene diphosgene
  • triphosgene triphosgene
  • the reaction is usually performed in a solvent.
  • 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.
  • sulfoxides such as dimethyl sulfoxide, nitriles such as acetonitrile and propionitrile, water, and mixtures thereof.
  • 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.
  • phosgene is usually used at a ratio of 1 to 10 mol
  • base is used at a ratio of 1 to 10 mol.
  • 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.
  • 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.
  • the compound of the present invention may be used alone.
  • 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%.
  • solid carrier examples 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.
  • 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.
  • liquid carrier examples 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.
  • 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.
  • surfactant examples 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.
  • formulation adjuvants include, for example, fixing agents, dispersants, and stabilizers.
  • 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.
  • polysaccharides eg, starch, arabic gum, cellulose derivatives, alginic acid
  • lignin derivatives Bentonite
  • sugars synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyr
  • 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 (register
  • 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.
  • 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.
  • 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.
  • 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.,
  • 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).
  • plants include genetically modified crops.
  • 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
  • Rice 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 a
  • 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.
  • 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.
  • Carposinidae Coffee Leaf miner (Leucoptera coffeella), peach leaf moth (Lyonetia clerkella), winged leaf moth (Lyonetia prunifoliella), etc. Lymantriidae such as Euproctis spp.
  • 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.
  • 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 colaspi
  • 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 subfasciat
  • Tribolium castaneum, Tribolium confusum, 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),ixie 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. ridi
  • 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 ⁇ 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 (Reticuli
  • R 3 is represented by the following:
  • 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] phen
  • 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.
  • plant disease control agents such as fungicides, insecticides, acaricides, nematocides, plant growth regulators or synergists
  • this component fungicides, insecticides, acaricides, nematocides, plant growth regulators or synergists
  • 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.
  • 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.
  • 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 ⁇ L into a titer plate (96 well) 150 ⁇ L 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.
  • PDB medium potato broth liquid medium
  • 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 ⁇ L into a titer plate (96-well), 150 ⁇ L 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.
  • PDB medium potato broth liquid medium
  • 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 ⁇ L 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 ⁇ L. This plate was cultured at 18 ° C.
  • PDB medium tomato leaf mold Potato broth liquid medium
  • 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.
  • 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.
  • 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.
  • 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.
  • the wheat was air-dried and then placed under illumination for 11-14 days, after which the lesion area was examined.
  • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un composé oxadiazole représenté par la formule (I) [dans laquelle R1 représente un atome d'halogène ou un groupe alkyle en C1-C2 ; n représente un entier de 0 à 2; et R2 représente un groupe alkyle en C2-C6 ou un groupe alcényle en C3-C4] ayant un excellent effet de lutte contre les maladies des plantes.
PCT/JP2017/010881 2016-03-31 2017-03-17 Composé oxadiazole et utilisation associée Ceased WO2017169893A1 (fr)

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JP2016-070630 2016-03-31
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JP2016105928 2016-05-27
JP2016-105928 2016-05-27

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
WO2019171234A1 (fr) 2018-03-09 2019-09-12 Pi Industries Ltd. Composés hétérocycliques en tant que fongicides
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
WO2020070610A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd. Nouveaux oxadiazoles
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11083196B2 (en) 2016-03-24 2021-08-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11192867B2 (en) 2016-06-03 2021-12-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11974572B2 (en) 2017-03-31 2024-05-07 Sygenta Participations Ag Fungicidal compositions

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JPS63162680A (ja) * 1986-12-12 1988-07-06 チバーガイギー　アクチエンゲゼルシヤフト オキサジアゾール誘導体およびそれを含む有害生物防除剤組成物
JPH04182403A (ja) * 1990-11-16 1992-06-30 Tosoh Corp チアジアゾール誘導体を有効成分として含有する殺菌剤
JP2002114751A (ja) * 2000-08-04 2002-04-16 Aventis Cropscience Sa 殺菌性のフェニル（チオ）ウレア及びフェニル（チオ）カーバメートの誘導体

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JPS63162680A (ja) * 1986-12-12 1988-07-06 チバーガイギー　アクチエンゲゼルシヤフト オキサジアゾール誘導体およびそれを含む有害生物防除剤組成物
JPH04182403A (ja) * 1990-11-16 1992-06-30 Tosoh Corp チアジアゾール誘導体を有効成分として含有する殺菌剤
JP2002114751A (ja) * 2000-08-04 2002-04-16 Aventis Cropscience Sa 殺菌性のフェニル（チオ）ウレア及びフェニル（チオ）カーバメートの誘導体

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11180462B2 (en) 2015-10-02 2021-11-23 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11066375B2 (en) 2015-10-02 2021-07-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11259524B2 (en) 2016-01-08 2022-03-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11083196B2 (en) 2016-03-24 2021-08-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11192867B2 (en) 2016-06-03 2021-12-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11974572B2 (en) 2017-03-31 2024-05-07 Sygenta Participations Ag Fungicidal compositions
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
US11286242B2 (en) 2018-01-30 2022-03-29 Pi Industries Ltd. Oxadiazoles for use in controlling phytopathogenic fungi
WO2019171234A1 (fr) 2018-03-09 2019-09-12 Pi Industries Ltd. Composés hétérocycliques en tant que fongicides
WO2020070610A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd. Nouveaux oxadiazoles
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides

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