Classifications

• • 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
• • 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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • 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
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Definitions

• Patent Literature 1 Various compounds for controlling plant diseases have been developed so far (see Patent Literature 1).
• An object of the present invention is to provide a compound having excellent control efficacies against plant diseases.
• a compound represented by formula (1) (wherein: X represents a C3-C5 alkyl group or a NR 1 R 2 ; R 1 represents a C1-C3 alkyl group; R 2 represents a C2-C3 alkyl group; and R 3 , R 4 , R 5 , and R 6 represent each independently a hydrogen atom or a fluorine atom) (hereinafter referred to as "compound of the present invention” or "Present compound”).
• the present invention can control plant diseases.
• C3-C5 alkyl group examples include n-propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, 1-methylbutyl group, 2-methylbutyl group, and n-pentyl group.
• C3-C5 alkyl group in X is a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, and a tert-butyl group.
• Examples of "C1-C3 alkyl group” include methyl group, ethyl group, n-propyl group, and isopropyl group.
• Preferable "C1-C3 alkyl group” in R 1 is a methyl group.
• Examples of "C2-C3 alkyl group” include ethyl group, n-propyl group, and isopropyl group.
• Preferable "C2-C3 alkyl group” in R 2 is an ethyl group.
• the compound of the present invention includes optical isomers each singly and any mixture composed of these isomers each in an arbitrary ratio of the respective isomer.
• the compound of the present invention may form an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate, and benzoate by mixing the compound with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid.
• an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid.
• Embodiments of the compound of the present invention include the following compounds.
• (Embodiment 1) The compound of the present invention, wherein X represents a C3-C5 alkyl group.
• (Embodiment 2) The compound of the present invention, wherein X represents a n-propyl group, an isopropyl group, or a butyl group.
• (Embodiment 3) The compound of the present invention, wherein X represents a C3-C5 alkyl group, and R 3 , R 4 , R 5 , and R 6 represent each a hydrogen atom.
• the compound of the present invention can be prepared, for example, according to the following processes.
• the compound of the present invention may be prepared by reacting the compound represented by formula (A1) (hereinafter referred to as "Compound (A1)”) with the compound represented by formula (A2) (hereinafter referred to as “Compound (A2)”) in the presence of a base. (wherein the symbols are the same as defined above.) The reaction is usually carried out in a solvent.
• hydrocarbons such as n-hexane, cyclohexane, toluene, and xylene
• hydrocarbons such as diethyl ether, tetrahydrofuran (hereinafter referred to as "THF"), 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether (hereinafter collectively referred to as “ethers”)
• halogenated hydrocarbons such as chloroform, dichloromethane, and chlorobenzene (hereinafter collectively referred to as "halogenated hydrocarbons”)
• amides such as N,N-dimethylformamide (hereinafter referred to as "DMF"), 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone (hereinafter collectively referred to as "amide
• Examples of the base to be used in the reaction include organic bases such as triethylamine, pyridine, 2,2’-bipyridine, and diazabicycloundecene (hereinafter collectively referred to as "organic bases”); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter collectively referred to as “alkali metal carbonates”); alkali metal hydrogen carbonates such as sodium hydrogen carbonate (hereinafter collectively referred to as “alkali metal hydrogen carbonates”); alkali metal hydrides such as sodium hydride (hereinafter collectively referred to as “alkali metal hydrides”); and mixtures thereof.
• the Compound (A1) may be in a form of salt.
• Examples of the salt of the Compound (A1) include hydrochloride and sulfate.
• 1 to 10 mols of the Compound (A2) is usually used, and 1 to 20 mols of the base is usually used, per mol of the Compound (A1).
• the reaction temperature of the reaction is usually within a range of -20 to 150°C.
• the reaction period of the reaction is usually within a range of 0.1 to 120 hours.
• the reaction mixtures are mixed with water and then extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to isolate the compound of the present invention.
• the Compound (A1) may be prepared according to the process described in WO 2016/031815 pamphlet.
• the Compound (A2) is known.
• Process B The compound represented by formula (1-A) (hereinafter referred to as "Compound (1-A)”) may be prepared according to the following scheme. (wherein the symbols are the same as defined above.)
• This process includes (1) a step of preparing the compound represented by formula (A3) (hereinafter referred to as "Compound (A3)”) from the Compound (A1) (First step); and (2) a step of preparing the Compound (1-A) from the Compound (A3) (Second step).
• the Compound (A3) may be prepared by reacting the Compound (A1) with phosgene, diphosgene, or triphosgene in the presence of a base.
• the reaction may be carried out according to the process described in Synthetic Communications, 2007, 37, 1037.
• the Compound (A3) may be directly used in the Second step without isolating it, or the residues obtained by concentrating the reaction mixtures may be directly used in the Second step.
• the Compound (1-A) may be prepared by reacting the Compound (A3) with the compound represented by formula (A4) (hereinafter referred to as "Compound (A4)").
• the reaction is usually carried out in a solvent.
• the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures thereof.
• 1 to 10 mols of the Compound (A4) is usually used per mol of the Compound (A3).
• the reaction temperature of the reaction is usually within a range of -20 to 100°C.
• the reaction period of the reaction is usually within a range of 0.1 to 120 hours.
• the reaction mixtures are mixed with water and then extracted with organic solvent(s), and the organic layers are worked up (for example, dried or concentrated) to isolate compound (1-A).
• the Compound (A4) is known.
• the compound of the present invention may also be prepared from the compound represented by formula (A5) (hereinafter referred to as "Compound (A5)”) according to the following scheme. (wherein the symbols are the same as defined above.)
• This process includes (1) a step of preparing the compound represented by formula (A6) (hereinafter referred to as "Compound (A6)”) from the Compound (A5) (First step); (2) a step of preparing the compound represented by formula (A7) (hereinafter referred to as “Compound (A7)”) from the Compound (A6) (Second step); and (3) a step of preparing the compound of the present invention from the Compound (A7) (Third step).
• the Compound (A6) may be prepared by reacting the Compound (A5) with the Compound (A2) in the presence of a base. The reaction may be carried out according to the process described in the Process A.
• the Compound (A5) is known.
• the Compound (A7) may be prepared by reacting the Compound (A6) with hydroxylamine.
• the reaction may be carried out according to the process described in Organic Letters, 2014, 16, 892.
• the compound of the present invention may be prepared by reacting the Compound (A7) with trifluoroacetic anhydride in the presence of a base.
• the reaction is usually carried out in a solvent.
• the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols such as methanol and ethanol (hereinafter referred to as “alcohols”), and mixed solvents thereof.
• the base to be used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, alkali metal hydrides, and mixtures thereof.
• reaction 1 to 10 mols of the trifluoroacetic anhydride is usually used, and 1 to 10 mols of the base is usually used, per mol of the Compound (A7).
• the reaction temperature of the reaction is usually within a range of -20 to 150°C.
• the reaction period of the reaction is usually within a range of 0.1 to 120 hours.
• the control agent of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier, a liquid carrier, a surfactant, and/or the others, and if necessary, adding auxiliary agents for formulation such as binders, dispersants, and stabilizers, to formulate into wettable powders, granular wettable powders, flowables, granules, dry flowables, emulsifiable concentrates, aqueous solutions, oil solutions, smoking agents, aerosols, microcapsules, poison baits, resin formulations, shampoo formulations, paste-like formulations, foams, carbon dioxide formulations, tablets, or the others.
• Such formulations comprise usually 0.1 to 99% by weight, and preferably 0.2 to 90% by weight of the compound of the present invention.
• the solid carrier examples include fine powders or granules of clays (for example, kaolin, diatomaceous earth, synthetic hydrated silicon oxides, Fubasami clay, bentonite, or acid white clay), talcs, other inorganic minerals (for example, sericite, quartz powder, sulfur powder, active carbon, calcium carbonate, or hydrated silica), and the others.
• clays for example, kaolin, diatomaceous earth, synthetic hydrated silicon oxides, Fubasami clay, bentonite, or acid white clay
• talcs other inorganic minerals (for example, sericite, quartz powder, sulfur powder, active carbon, calcium carbonate, or hydrated silica), and the others.
• liquid carrier examples include water, alcohols, ketones (for example, acetone, methylethylketone, or cyclohexanone), aromatic hydrocarbons (for example, benzene, toluene, xylene, ethyl benzene, or methylnaphthalene), aliphatic hydrocarbons (for example, n-hexane or kerosene), esters, nitriles, ethers, amides, halogenated hydrocarbons, and the others.
• ketones for example, acetone, methylethylketone, or cyclohexanone
• aromatic hydrocarbons for example, benzene, toluene, xylene, ethyl benzene, or methylnaphthalene
• aliphatic hydrocarbons for example, n-hexane or kerosene
• esters for example, nitriles, ethers, amides, halogen
• surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylated compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
• auxiliary agents for formulation examples include binders, dispersants, and stabilizers. Specific examples include casein, gelatin, polysaccharides (for example, starch, gum arabic, cellulose derivatives, or alginic acid), lignin derivatives, bentonite, saccharides, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, or polyacrylic acids), acidic isopropyl phosphate, 2,6-di-tert-butyl-4-methylphenol, a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol, vegetable oils, mineral oils, and fatty acids and esters thereof.
• polysaccharides for example, starch, gum arabic, cellulose derivatives, or alginic acid
• lignin derivatives bentonite
• saccharides for example, polyvinyl alcohol, polyvinyl pyrrolidone, or polyacrylic acids
• the compound of the present invention may be mixed with an oil such as mineral oil and vegetable oil, a surfactant, or the others to use for controlling plant diseases.
• oil or the surfactant to be mixed with the compound of the present invention include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (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), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpra
• the application dose of the compound of the present invention may be varied depending on a climate condition, a dosage form, an application period, an application method, an application site, a disease to be controlled, a kind of crop to be applied, and the like.
• the amount of the compound of the present invention in the control agent of the present invention is usually within the range of 1 to 500 g, and preferably 2 to 200 g, per 1000 m 2 .
• the emulsifiable concentrates, the wettable powders, or suspensions etc. are usually applied by diluting them with water, and then spreading them. In this case, the concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, and preferably 0.005 to 2% by weight.
• the dusts or the granules, etc. are usually applied as itself without diluting them.
• the method for applying the compound of the present invention is not limited to a specific method as long as the compound of the present invention can be applied.
• Examples of the method include an application to a plant body such as a foliar application, an application to a cultivation area of plant such as a soil treatment, an application to seeds such as a seed disinfection, and an application to harmful arthropods.
• the amount of the compound of the present invention is usually within the range of 1 to 500 g per 1000 m 2 of the soil.
• the amount of the compound of the present invention in the control agent of the present invention is usually within the range of 0.001 to 100 g, and preferably 0.01 to 50 g per 1 Kg of seeds.
• the emulsifiable concentrates, the wettable powders, or the flowables, etc. are usually applied by diluting them with water, and then spreading them.
• the concentration of the compound of the present invention is usually within the range of 0.0005 to 2% by weight.
• the dusts or the granules, etc. are usually applied as itself without diluting them.
• the compound of the present invention may be used as an agent for controlling plant diseases in croplands such as fields, paddy fields, grasses, and orchards.
• the compound of the present invention can control cropland diseases in the croplands etc. for cultivating the following plant(s) etc. Further, the compound of the present invention can control harmful arthropods in the croplands.
• Crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rapeseed, sunflower, sugar cane, tobacco, and the others;
• Vegetables solanaceous vegetables (for example, eggplant, tomato, pimento, pepper, or potato), cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini, water melon, or melon), cruciferous vegetables (for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, or cauliflower), asteraceous vegetables (for example, burdock, crown daisy, artichoke, or lettuce), liliaceous vegetables (for example, welsh onion, onion, garlic, or asparagus), ammiaceous vegetables (for example, carrot, parsley, celery, or parsnip), chenopodiaceous vegetables (for example, spinach or Swiss chard), lamiaceous vegetables (for example,
• plants(s) may include genetically modified plant(s).
• Examples of the plant disease which may be controlled by the compound of the present invention include diseases caused by a plant pathogen such as filamentous fungi and bacteria. Specific examples of the plant disease include, but are not limited to, the followings. The scientific name of each pathogen which causes the disease is shown in parentheses.
• Rice diseases blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), and downy mildew (Sclerophthora macrospora); Wheat diseases: powdery mildew (Blumeria graminis), Fusarium blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), stripe rust (Puccinia striiformis), stem rust (Puccinia graminis), leaf rust (Puccinia recondita), snow mold (Microdochium nivale, Microdochium majus), typhula snow blight (Typhula incarnata, Typhula ishikariensis), loose smut (Ustilago tritici), stink
• Examples of the harmful arthropod to be controlled by the compound of the present invention include the followings. Hemiptera pests: Delphacidae (for example, Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, or Tagosodes orizicolus); Cicadellidae (for example, Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, or Cofana spectra); Cercopidae (for example, Mahanarva posticata or Mahanarva fimbriolata); Aphididae (for example, Aphis fabae, Aphis glycines, Aphis goss
• Lepidoptera pests Crambidae (for example, Chilo suppressalis, Chilo polychrysus (Darkheaded stem borer), Scirpophaga innotata (White stem borer), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis (European corn borer), Hellula undalis, Herpetogramma luctuosale, Pediasia teterrellus, Nymphula depunctalis, or Diatraea saccharalis (Sugarcane borer)); Pyralidae (for example, Elasmopalpus lignosellus or Plodia interpunctella); Noctuidae (for example, Spodoptera litura, Spodoptera exigu
• Pluteliidae for example, Plutella xylostella
• Gelechiidae for example, Anarsia lineatella, Helcystogramma triannulellum, Pectinophora gossypiella, Phthorimaea operculella, or Tuta absolutea
• Arctiidae for example, Hyphantria cunea
• Castniidae for example, Telchin licus (Giant Sugarcane borer)
• Cossidae for example, Cosus insularis
• Geometridae for example, Ascotis selenaria
• Limacodidae for example, Parasa lepida
• Stathmopodidae for example, Stathmopoda tenussa
• Thysanoptera pests for example, Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, or Echinothrips americanus); Phlaeothripidae (for example, Haplothrips aculeatus); and the others.
• Diptera pests Anthomyiidae (for example, Delia platura or Delia antiqua); Ulidiidae (for example, Tetanops myopaeformis); Agromyzidae (for example, Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, or Chromatomyia horticola); Chloropidae (for example, Chlorops oryzae); Tephritidae (for example, Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, or Ceratitis capitata); Ephydridae (for example, Hydrellia griseola, Hydrellia philippina, or Hydrellia sasakii); Drosophilidae (for example, Drosophila suzukii); Phoridae (for example
• Coleoptera pests Chrysomelidae (for example, Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae, Diabrotica balteata, Diabrotica speciosa (Cucurbit Beetle), Cerotoma trifurcata, Oulema melanopus, Aulacophora femoralis, Phyllotreta striolata, Phyllotreta cruciferae (Cabbage flea beetle), Phyllotreta pusilla (Western black flea beetle), Psylliodes chrysocephala (Cabbage stem flea beetle), Leptinotarsa decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Chaetocnema confi, Epitrix cucumer
• Curculionidae for example, Araecerus coffeae, Cylas formicarius, Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineatocollis, Anthonomus grandis, Sphenophorus venatus, Sphenophorus callosus (Southern Corn Billbug), Sternechus subsignatus (Soybean stalk weevil), Sphenophorus levis (Sugarcane weevil), Scepticus griseus, Scepticus uniformis, Zabrotes subfasciatus, Tomicus piniperda, Hypothenemus hampei (Coffee Berry Borer), Aracanthus s
• Curculionidae for example, Araecerus coffeae, Cylas formicarius, Euscepes postf
• Orthoptera pests for example, Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina (Brown Locust), Anacridium melanorhodon (Tree Locust), Calliptamus italicus (Italian Locust), Melanoplus differentialis (Differential grasshopper), Melanoplus bivittatus (Two striped grasshopper), Melanoplus sanguinipes (Migratory grasshopper), Melanoplus femurrubrum (Red-Legged grasshopper), Camnula pellucida (Clearwinged grasshopper), Schistocerca gregaria, Gastrimargus musicus (Yellow-winged locust), Austracris guttulosa (Spur-throated locust), Oxya yezoensis, Oxya yezoen
• Hymenoptera pests Tenthredinidae (for example, Athalia rosae or Athalia japonica); Solenopsis spp.; Formicidae (for example, Atta capiguara (Brown leaf-cutting ant)); and the others.
• Blattodea pests Blattellidae (for example, Blattella germanica); Blattidae (for example, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, or Blatta orientalis); Termitidae (for example, Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, or Cornitermes
• Me represents a methyl group
• Et represents an ethyl group
• Pr represents a n-propyl group
• i-Pr represents an isopropyl group
• Bu represents a n-butyl group
• Pen represents a n-pentyl group.
• Preparation example 1-2 The compounds prepared according to the process described in the Preparation example 1-1 and the physical properties thereof are shown below.
• Preparation example 3-2 The compounds prepared according to the process described in the Preparation example 3-1 and the physical properties thereof are shown below.
• the compound of the present invention wherein the combination of X, R 3 , R 4 , R 5 , and R 6 is any one of the combinations described in Compound numbers A1 to A69 may be prepared according to the above processes.
• the compounds of the present invention defined by Compound numbers A1 to A69 are collectively referred to as "Present compounds A1 to A69", and the “Present compounds A1 to A69” are collectively referred to as "Present compound A”.
• the Present compound A4 is the compound of the present invention wherein X, R 3 , R 4 , R 5 , and R 6 represent the combination described in the Compound number A4, and represented by the following structure.
• the Present compound can be mixed with or used in combination with a fungicidal active ingredient, an insecticidal active ingredient, a miticidal active ingredient, a nematicidal active ingredient, a plant growth regulatory component, or a synergist (hereinafter collectively referred to as "Present ingredient").
• a fungicidal active ingredient an insecticidal active ingredient, a miticidal active ingredient, a nematicidal active ingredient, a plant growth regulatory component, or a synergist
• Present ingredient examples of the combination of the Present compound and the Present ingredient are described.
• tebuconazole+SX represents the combination of "tebuconazole” and "SX”.
• SX indicates any one compound selected from the Present compounds A1 to A69.
• the number in parentheses represents the CAS registration number.
• 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, epoxiconazole+SX, cyproconazole+SX, mandestrobin+SX, azoxystrobin+SX, pyraclostrobin+SX, trifloxystrobin+SX, fluoxastrobin+SX, picoxystrobin+SX, fenamidone+SX, dimoxystrobin+SX, metominostrobin+SX, pyribencar
• Examples of the mixture ratio of the Present compound and the Present ingredient include, but are not limited to, 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 to 1:100, 1:1 to 1:50, 1:1 to 1:20, and 1:1 to 1:10 in the ratio by weight (Present compound : Present ingredient).
• Applying the Present compound to a plant achieves efficacies for promoting the plant growth such as the increase in the rate of seedling establishment, increase in the number of healthy leaves, increase in the height of the plant, increase in the weight of the plant, increase in the leaf area, increase in the number or weight of seeds or fruits, increase in the number of occasion of flower setting or fruit setting, and promoted growth of a root. Also, applying the Present compound to a plant achieves the improvement in tolerance to abiotic stresses such as temperature stresses (for example, high-temperature stress and low-temperature stress), water stresses (for example, drought stress and excess water stress), and salt stresses.
• temperature stresses for example, high-temperature stress and low-temperature stress
• water stresses for example, drought stress and excess water stress
• salt stresses for example, high-temperature stress and low-temperature stress
• Formulation example 1 Fifty(50) parts of any one of the Present compound A, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic hydrated silicon oxide are fully ground and mixed to obtain each formulation.
• Formulation example 2 Twenty(20) parts of any one of the Present compound A, 1.5 parts of sorbitan trioleate, and 28.5 parts of an aqueous solution comprising 2 parts of polyvinyl alcohol are mixed and finely ground by a wet grinding method, and then 40 parts of an aqueous solution comprising 0.05 parts of xanthane gum and 0.1 part of aluminum magnesium silicate is added thereto, and 10 parts of propylene glycol is further added thereto, and the resulting mixture is mixed with stirring to obtain each formulation.
• Formulation example 3 Two(2) parts of any one of the Present compound A, 88 parts of kaolin clay, and 10 parts of talc are fully ground and mixed to obtain each formulation.
• Formulation example 4 Five(5) parts of any one of the Present compound A, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are fully mixed to obtain each formulation.
• Formulation example 5 Two(2) parts of any one of the Present compound A, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are fully ground and mixed, and then water is added thereto, and the resulting mixture is fully kneaded, and granulated and dried to obtain each formulation.
• Formulation example 6 Thirty-five (35) parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1:1), 20 parts of any one of the Present compound A, and 45 parts of water are fully mixed to obtain each formulation.
• Test examples are used to show efficacies of the Present compounds on controlling plant diseases.
• Test example 1 Test for controlling Septoria leaf blotch (Septoria tritici) on wheat
• the Present compound 1, 2, 3, 5, 7, 8, 11, or 12 was diluted with dimethyl sulfoxide such that each concentration of the Present compound was 1500 ppm.
• the resultant dilute solution was dispensed into a microtiter plate (with 96 wells) in 1 ⁇ L portion thereof per well. Thereto was then dispensed 150 ⁇ L of a potato dextrose broth medium (PDB medium) to which spores of Septoria tritici were inoculated in advance.
• PDB medium potato dextrose broth medium
• This plate was cultured at 18°C for five days, thereby allowing Septoria tritici to undergo proliferation, and the absorbance at 550 nm of each well of the microtiter plate was then measured, and the obtained value was used as the degree of growth of Septoria tritici. From the test results, each degree of growth in the group treated with the Present compound 1, 2, 3, 5, 7, 8, 11, or 12 was 50% or less as compared to the degree of growth in the untreated group.
• Test example 2 Test for controlling leaf mold (Cladosporium fulvum) on tomato The Present compound 1, 2, 3, 4, 5, 6, 7, 8, or 12 was diluted with dimethyl sulfoxide such that each concentration of the Present compound was 1500 ppm. The resultant dilute solution was dispensed into a microtiter plate (with 96 wells) in 1 ⁇ L portion thereof per well.
• Test example 3 Test for controlling anthracnose (Colletotrichum truncatum) on soybean
• the Present compound 7 was diluted with dimethyl sulfoxide such that the concentration of the Present compound was 1500 ppm.
• the resultant dilute solution was dispensed into a microtiter plate (with 96 wells) in 1 ⁇ L portion thereof per well. Thereto was then dispensed 150 ⁇ L of a potato dextrose broth medium (PDB medium) to which spores of Colletotrichum truncatum were inoculated in advance.
• PDB medium potato dextrose broth medium
• This plate was cultured at 18°C for four days, thereby allowing Colletotrichum truncatum to undergo proliferation, and the absorbance at 550 nm of each well of the microtiter plate was then measured, and the obtained value was used as the degree of growth of Colletotrichum truncatum. From the test results, the degree of growth in the group treated with the Present compound 7 was 50% or less as compared to the degree of growth in the untreated group.
• Test example 4 Test for controlling rust (Puccinia recondita) on wheat A plastic pot was filled with soil, and thereto wheat (cultivar. Shirogane) was seeded, and the wheat was cultivated in a greenhouse for nine days. Separately, the Present compound 1, 2, 4, 5, 8, or 11 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 500 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above wheat. After spraying the mixture, the wheat was air-dried, and cultivated at 20°C under lighting for five days, and then spores of Puccinia recondita were inoculated by dusting thereto.
• each lesion area in the group of wheat treated with the Present compound 1, 2, 4, 5, 8, or 11 was 30% or less as compared to the lesion area in the untreated group of wheat.
• Test example 5 Test for controlling rust (Puccinia recondita) on wheat A plastic pot was filled with soil, and thereto wheat (cultivar. Shirogane) was seeded, and the wheat was cultivated in a greenhouse for nine days. Separately, the Present compound 1, 2, 3, 4, 5, 8, or 11 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 200 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above wheat. After spraying the mixture, the wheat was air-dried, and cultivated at 20°C under lighting for five days, and then spores of Puccinia recondita were inoculated by dusting thereto.
• each lesion area in the group of wheat treated with the Present compound 1, 2, 3, 4, 5, 8, or 11 was 30% or less as compared to the lesion area in the untreated group of wheat.
• Test example 6 Test for controlling Septoria leaf blotch (Septoria tritici) on wheat A plastic pot was filled with soil, and thereto wheat (cultivar. Apogee) was seeded, and the wheat was cultivated in a greenhouse for ten days. Separately, the Present compound 1, 2, 8, or 11 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 500 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above wheat. After spraying the mixture, the wheat was air-dried, and four days after the application, an aqueous suspension of spores of Septoria tritici was inoculated by spraying thereto.
• each lesion area in the group of wheat treated with the Present compound 1, 2, 8, or 11 was 30% or less as compared to the lesion area in the untreated group of wheat.
• Test example 7 Test for controlling Septoria leaf blotch (Septoria tritici) on wheat A plastic pot was filled with soil, and thereto wheat (cultivar. Apogee) was seeded, and the wheat was cultivated in a greenhouse for ten days. Separately, the Present compound 1, 2, or 11 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 200 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above wheat. After spraying the mixture, the wheat was air-dried, and four days after the application, an aqueous suspension of spores of Septoria tritici was inoculated by spraying thereto.
• each lesion area in the group of wheat treated with the Present compound 1, 2, or 11 was 30% or less as compared to the lesion area in the untreated group of wheat.
• Test example 8 Test for controlling scald (Rhynchosporium secalis) on barley A plastic pot was filled with soil, and thereto barley (cultivar. Nishinohoshi) was seeded, and the barley was cultivated in a greenhouse for seven days. Separately, the Present compound 11 formulated according to the process described in the Formulation example 6 was mixed with water such that the concentration of the Present compound was 200 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above barley.
• the barley After spraying the mixture, the barley was air-dried, and one day after the application, an aqueous suspension of spores of Rhynchosporium secalis was inoculated by spraying thereto. After the inoculation, the barley was placed at 15°C under humid condition for three days, and then cultivated in a greenhouse for fourteen days, and then the lesion area was examined. From the test results, the lesion area in the group of barley treated with the Present compound 11 was 30% or less as compared to the lesion area in the untreated group of barley.
• Test example 9 Test for controlling net blotch (Pyrenophora teres) on barley A plastic pot was filled with soil, and thereto barley (cultivar. Nishinohoshi) was seeded, and the barley was cultivated in a greenhouse for seven days. Separately, the Present compound 5 formulated according to the process described in the Formulation example 6 was mixed with water such that the concentration of the Present compound was 500 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above barley.
• the barley After spraying the mixture, the barley was air-dried, and two days after the application, an aqueous suspension of spores of Pyrenophora teres was inoculated by spraying thereto. After the inoculation, the barley was placed at 23°C in daytime and at 20°C in nighttime in a greenhouse under humid condition for three days, and then cultivated in a greenhouse for seven days, and then the lesion area was examined. From the test results, the lesion area in the group of barley treated with the Present compound 5 was 30% or less as compared to the lesion area in the untreated group of barley.
• Test example 10 Test for controlling rust (Phakopsora pachyrhizi) on soybean A plastic pot was filled with soil, and thereto soybeans (cultivar. Kurosengoku) were seeded, and the soybeans were cultivated in a greenhouse for ten days, and an aqueous suspension of uredospores of Phakopsora pachyrhizi was inoculated by spraying thereto. After the inoculation, the soybeans were placed at 23°C in daytime and at 20°C in nighttime in a greenhouse under humid condition for one day, and then cultivated in a greenhouse for two days.
• the Present compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 200 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above soybeans. After spraying the mixture, the soybeans were air-dried, and cultivated in a greenhouse for eight days, and then the lesion area was examined. From the test results, each lesion area in the group of soybeans treated with the Present compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 was 30% or less as compared to the lesion area in the untreated group of soybeans.
• Test example 11 Test for controlling rust (Phakopsora pachyrhizi) on soybean A plastic pot was filled with soil, and thereto soybeans (cultivar. Kurosengoku) were seeded, and the soybeans were cultivated in a greenhouse for thirteen days. Separately, the Present compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 200 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above soybeans.
• each lesion area in the group of soybeans treated with the Present compound 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 was 30% or less as compared to the lesion area in the untreated group of soybeans.
• Test example 12 Test for controlling blast (Magnaporthe grisea) on rice A plastic pot was filled with soil, and thereto rice (cultivar. Hinohikari) was seeded, and the rice was cultivated in a greenhouse for twenty days.
• the Present compound 1, 2, or 8 formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the Present compound was 500 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above rice. After spraying the mixture, the rice was air-dried, and the above spray-treated rice was placed at 24°C in daytime and at 20°C in nighttime under humid condition for six days in contact with rice seedlings (cultivar.
• Test example 13 Test for controlling blast (Magnaporthe grisea) on rice A plastic pot was filled with soil, and thereto rice (cultivar. Hinohikari) was seeded, and the rice was cultivated in a greenhouse for twenty days.
• the Present compound 8 formulated according to the process described in the Formulation example 6 was mixed with water such that the concentration of the Present compound was 200 ppm. Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above rice. After spraying the mixture, the rice was air-dried, and the above spray-treated rice was placed at 24°C in daytime and at 20°C in nighttime under humid condition for six days in contact with rice seedlings (cultivar.
• Reference test example 1 The Present compound 11 formulated according to the process described in the Formulation example 6 was mixed with water such that the concentration of the Present compound was 500 ppm. Said mixed solution was sprayed to the foliar parts of cabbage seedlings (on the developmental stage of the second to the third true leaf) planted in a container so as to adhere adequately onto the surfaces of leaves of the above cabbage seedlings. After spraying the mixture, the cabbage seedlings were air-dried, and the stem and leaf parts of these seedlings were cut out, and placed in a container lined with a filter paper. Five heads of cabbage moth (Plutella xylostella) at the second instar larval stages were released into the container.
• Comparative test example A plastic pot was filled with soil, and thereto soybeans (cultivar. Kurosengoku) were seeded, and the soybeans were cultivated in a greenhouse for thirteen days.
• a formulated according to the process described in the Formulation example 6 was mixed with water such that each concentration of the compound was 12.5 ppm.
• Said mixture was sprayed to the foliar parts so as to adhere adequately onto the surfaces of leaves of the above soybeans.
• the soybeans were air-dried, and four days after the application, an aqueous suspension of spores of Phakopsora pachyrhizi was inoculated by spraying thereto.
• the soybeans were placed at 23°C in daytime and at 20°C in nighttime in a greenhouse under humid condition for one day, and then cultivated in a greenhouse for ten days, and then the lesion area was examined.
• each lesion area in the group of soybeans treated with the Present compound 1 or 11 was 10% or less as compared to the lesion area in the untreated group of soybeans
• each lesion area in the group of soybeans treated with the Compound 3.2 or the Compound 3.14 described in JP S63-162680 A was 76% or more as compared to the lesion area in the untreated group of soybeans under the same conditions as shown in Table 1.
• the compound of the present invention has control efficacies against plant diseases and useful as an active ingredient of an agent for controlling plant diseases.

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