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WO2011090127A1 - Dérivé de triazolopyridine ou sel de cette dernière et son utilisation dans un agent de lutte contre un organisme nocif - Google Patents

Dérivé de triazolopyridine ou sel de cette dernière et son utilisation dans un agent de lutte contre un organisme nocif Download PDF

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Publication number
WO2011090127A1
WO2011090127A1 PCT/JP2011/051001 JP2011051001W WO2011090127A1 WO 2011090127 A1 WO2011090127 A1 WO 2011090127A1 JP 2011051001 W JP2011051001 W JP 2011051001W WO 2011090127 A1 WO2011090127 A1 WO 2011090127A1
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Prior art keywords
substituted
alkyl
compounds
salt
compound
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English (en)
Japanese (ja)
Inventor
寿彦 植木
和久 桐山
智裕 岡本
哲也 小玉
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Ishihara Sangyo Kaisha Ltd
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Ishihara Sangyo Kaisha Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A61P33/12—Schistosomicides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to a pest control agent containing a novel triazolopyridine derivative or a salt thereof as an active ingredient.
  • Patent Document 1 describes that a specific triazolopyridine derivative can be used as a medicine.
  • the Q moiety in the following formula (I) is limited to a substituted amino group unlike the compound of the present invention.
  • the use is also limited as a medicine.
  • An object of the present invention is to provide a pest control agent that has a high control effect on pests and has high safety for mammals and the like when used.
  • the triazolopyridine derivative represented by the following formula (I) is extremely low against pests at a low dose. It has been found that it has a control effect and has safety against crops, pest natural enemies or mammals, and has completed the present invention.
  • the present invention has the formula (I):
  • Cy is aryl substituted with X or heteroaryl substituted with X;
  • Q is a hydrogen atom, alkyl optionally substituted with A, cycloalkyl optionally substituted with U, substituted with A Alkenyl which may be substituted, alkynyl which may be substituted with A, halogen atom, cyano, aryl, heterocyclic group which may be substituted with alkyl, CH ⁇ NOR 2 , CH ⁇ NNR 4 R 5 , COR 2 , COOR 2 OR 2 , S (O) n R 3 or CONR 4 R 5 ;
  • R 1 is a hydrogen atom, alkyl optionally substituted with A, cycloalkyl optionally substituted with U, optionally substituted with A Good alkenyl, alkynyl optionally substituted with A, halogen atom, cyano, aryl, heterocyclic group optionally substituted with alkyl, CH ⁇ NOR 2 , CH ⁇ NNR 4 R 5 , COR 2
  • the triazolopyridine derivative of the formula (I) or a salt thereof is a novel compound, and a pest control agent containing these as an active ingredient has a very high control effect against pests with a low dose.
  • the substituents in Cy, Q and R 1 in formula (I) are described in detail below.
  • the number of substitutions for X, A or U may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different. Moreover, any position may be sufficient as the substitution position of X, A, or U, respectively.
  • halogen atom examples include fluorine, chlorine, bromine or iodine atoms.
  • the number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • Alkyl may be linear or branched, and for example, C 1-6 such as methyl, ethyl, propyl, isopropyl, butyl, tertiary butyl (hereinafter abbreviated as tert-butyl), pentyl, hexyl and the like. And so on.
  • cycloalkyl examples include C 3-6 such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • the alkenyl may be linear or branched, for example C 2-6 such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, 1-hexenyl. Etc.
  • the alkynyl may be linear or branched, for example, a C such as ethynyl, 2-butynyl, 2-pentynyl, 3-methyl-1-butynyl, 2-penten-4-ynyl, 3-hexynyl. 2-6 and the like.
  • Examples of the aryl include C 6-10 such as phenyl and naphthyl.
  • the heteroaryl may be monocyclic heteroaryl or condensed heteroaryl, and may contain 1 to 4 atoms selected from the group consisting of O, S and N. Specific examples thereof include 5-membered heteroaryl such as furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl Benzofuranyl, isobenzofuranyl, benzothienyl, isobenzothienyl, indolyl, isoindolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, quino
  • the heterocyclic group may be either a monocyclic heterocyclic group or a condensed heterocyclic group, and may contain 1 to 4 atoms selected from the group consisting of O, S and N. .
  • Specific examples thereof include 3-membered heterocyclic groups such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyrazolidinyl , Triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl and the like; 6-membered heterocyclic groups such as pyranyl, pyridyl,
  • Examples of the salt of the triazolopyridine derivative of the formula (I) include any salt as long as it is acceptable in the art, for example, alkali metal salts such as sodium salt and potassium salt; magnesium salt and calcium salt Alkaline earth metal salts such as: ammonium salts such as dimethylammonium salts and triethylammonium salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; such as acetates and methanesulfonates Organic acid salts and the like.
  • alkali metal salts such as sodium salt and potassium salt
  • Alkaline earth metal salts such as: ammonium salts such as dimethylammonium salts and triethylammonium salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; such as acetates and methanesulfonates Organic acid salts and the like
  • the triazolopyridine derivative of the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production methods [1], [2], [3] and usual salt production methods. .
  • the reaction flow will be described in detail below for each production method. Manufacturing method [1]
  • Y is a chlorine atom, bromine atom or iodine atom
  • M is ZnY, Sn (R 6 ) 3 , B (OH) 2 , B (OR 6 ) 2 or MgY
  • R 6 is Each independently alkyl or cycloalkyl
  • R 1 , Cy and Q are as defined above.
  • B (OR 6 ) 2 R 6 may be bonded to each other to form a ring.
  • This reaction can be carried out in the presence of a metal catalyst, if necessary.
  • metal catalysts include copper compounds; tin compounds; palladium compounds such as tetrakis (triphenylphosphine) palladium (0), bis (dibenzylideneacetone) palladium (0), tetrakis (dibenzylideneacetone) dipalladium (0) Of these, palladium compounds are preferred.
  • a co-catalyst can be used as needed.
  • the cocatalyst include metal halides such as lithium chloride.
  • This reaction can usually be performed in the presence of a base and a solvent.
  • the base include metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates such as sodium carbonate, potassium carbonate, cesium carbonate and calcium carbonate; sodium bicarbonate and potassium bicarbonate. 1 type or 2 types or more are appropriately selected from metal fluorides such as cesium fluoride and potassium fluoride; organic bases such as triethylamine, pyridine and 4- (N, N-dimethylamino) pyridine; Selected.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • water For example, water; alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane, Aliphatic hydrocarbons such as petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane; acetonitrile, propiononitrile Nitriles such as; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone; halogenated carbonization such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane Hydrogen And mixed solvents thereof.
  • aromatic hydrocarbons such as benz
  • the reaction temperature is usually 30 to 150 ° C., preferably 60 to 120 ° C.
  • the reaction time is usually 1 to 96 hours.
  • the compound of the formula (III) is a boron compound, it can be obtained on the market or synthesized according to a conventional method.
  • Cy-B (OH) 2 can be synthesized by reacting a halide such as CyI, CyBr or CyCl with trimethyl borate in the presence of a base such as tert-butyllithium. Manufacturing method [2]
  • R 7 is alkyl; R 1 , Cy and Q are as described above.
  • Examples of the compound of the formula (V) include tert-butyl nitrite and isoamyl nitrite.
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Ethers such as 1,4-dioxane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether
  • ketones such as acetone, methyl ethyl ketone, cyclohexanone
  • halogenation such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane Hydrocarbons; and mixed solvents thereof, among which ethers are desirable.
  • R 1 , Cy and Q are as described above.
  • This reaction can usually be performed in the presence of an acid and a solvent.
  • the acid include mineral acids such as hydrochloric acid, hydrobromic acid and nitric acid; carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid; and phosphoric acids such as polyphosphoric acid and diphosphoric acid.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Aliphatic hydrocarbons such as ligroin and petroleum benzine
  • ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane
  • methyl acetate and ethyl acetate Nitriles such as acetonitrile and propiononitrile
  • acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone
  • sulfoxides such as dimethyl sulfoxide
  • sulfolane Sulfones such as: phosphoric acid amides such as
  • the reaction temperature is usually 60 to 250 ° C., desirably 70 to 120 ° C.
  • the reaction time is usually 0.5 to 24 hours.
  • the compound of the formula (II) used in the production method [1] can be produced according to the production method [A] or the production method [B] shown below. Manufacturing method [A]
  • R 1 , R 7 , Q and Y are as described above.
  • the production method [A] can be performed according to the production method [2].
  • R 1 , Q and Y are as described above.
  • the production method [B] can be carried out according to the production method [3].
  • the compound of the formula (IVa) used in the production method [2] or the compound of the formula (IVb) used in the production method [A] can be produced according to the production method [C] shown below. Manufacturing method [C]
  • Z is Cy or Y; R 1 , R 7 , Q, Cy or Y is as described above.
  • the NH 2 OH salt includes any salt as long as it is acceptable in the technical field, and examples thereof include hydrochlorides and sulfates.
  • This reaction can usually be performed in the presence of a base.
  • the base include carbonates such as sodium carbonate, potassium carbonate, cesium carbonate and calcium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; triethylamine, tributylamine, diisopropylethylamine, pyrrolidine, piperidine and pyridine. 1 type (s) or 2 or more types are appropriately selected from such organic bases.
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Aliphatic hydrocarbons such as ligroin and petroleum benzine
  • ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane
  • acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone
  • sulfoxides such as dimethyl sulfoxide
  • sulfones such as
  • the reaction temperature is usually 0 to 200 ° C., preferably 5 to 120 ° C.
  • the reaction time is usually 1 to 24 hours.
  • the compound of formula (VIa) used in the production method [3] or the compound of formula (VIb) used in the production method [B] can be produced according to the production method [D] shown below. Manufacturing method [D]
  • T is OR 7 or N (R 8 ) 2 ; R 8 is each independently alkyl; R 1 , R 7 , Cy, Q, Y and Z are as described above.
  • This reaction can be performed in the presence of a base and a solvent, if necessary.
  • the base and the solvent include those similar to the above production method [C].
  • the solvent is not particularly limited as long as the reaction proceeds.
  • the reaction temperature is usually 0 to 200 ° C., preferably 20 to 80 ° C.
  • the reaction time is usually 6 to 48 hours.
  • the compound of formula (VII) used in the production method [C] can be produced according to the production method [E] shown below. Manufacturing method [E]
  • R 1 , R 7 , Q and Z are as described above.
  • This reaction can usually be performed in the presence of a solvent.
  • the solvent is not particularly limited as long as the reaction proceeds.
  • alcohols such as methanol, ethanol, propanol and butanol
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • Aliphatic hydrocarbons such as ligroin and petroleum benzine
  • ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane
  • Esters such as acetone, methyl ethyl ketone and cyclohexanone
  • nitriles such as acetonitrile and propiononitrile
  • acid esters such as N, N-dimethylformamide,
  • the reaction temperature is usually 0 to 120 ° C., preferably 50 to 100 ° C.
  • the reaction time is usually 0.5 to 5 hours.
  • the compound of the formula (VIII) used in the production method [D] can be produced according to the production method [F] shown below. Manufacturing method [F]
  • R 1 , R 7 , Q, T and Z are as described above.
  • This reaction can be performed in the presence of an acid and a solvent, if necessary.
  • the acid include mineral acids such as hydrochloric acid, hydrobromic acid and nitric acid; carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid; phosphoric acids such as polyphosphoric acid and diphosphoric acid; paratoluenesulfonic acid, And sulfonic acids such as methanesulfonic acid.
  • the solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [3].
  • the reaction temperature is usually from 80 to 200 ° C, preferably from 100 to 150 ° C.
  • the reaction time is usually 6 to 48 hours.
  • the desirable mode of the pest control agent containing the compound of the present invention is described below.
  • the pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasitics. It is particularly useful as a biocontrol agent.
  • the agricultural and horticultural pest control agent for example, it is useful as an insecticide, acaricide, nematicide or soil insecticide, specifically, a spider mite, a spider mite, a spider mite, a spider mite, an apple spider mite, Plant parasitic mites such as mite dust mites, citrus mites, mites, etc .; aphids such as peach aphids, cotton aphids, etc .; diamond moths, weevil, scallops, codling moths, ball worms, tobacco bad worms, maiiga, kobinomeiga, chanococa Agriculture such as spider anemone, Colorado potato beetle, cucumber potato beetle, ball weevil, leafhoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, Tamanaga, Kaburayaga, ants Pests; Plant parasitic nema
  • the agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is useful as an insecticide or an acaricide because it shows a further excellent effect in controlling plant parasitic mites and agricultural pests. Moreover, the agricultural and horticultural pest control agent containing the compound of the present invention is also effective in controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, synthetic pyrethroid agents, and neonicotinoid agents.
  • the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.
  • the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests and the like are comprehensively controlled.
  • Examples include horticultural pest control agents.
  • the agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, by mixing the compound with various agricultural adjuvants, It is used in various forms such as oily suspensions, granular aqueous solvents, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. Any formulation used in the art can be used.
  • Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water, Solvents such as toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol Fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates,
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • it can be used by appropriately selecting from those known in the art.
  • a bulking agent for example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction.
  • Various commonly used adjuvants such as agents, antifungal agents and the like can also be used.
  • the compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • the active ingredient concentration is preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the present invention per hectare.
  • the present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.
  • Application of various preparations or dilutions of agricultural and horticultural pesticides containing the compound of the present invention is usually performed by a commonly used application method, that is, spraying (for example, spraying, misting, atomizing). ), Dusting, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc.
  • spraying for example, spraying, misting, atomizing
  • Dusting water surface application, etc.
  • soil application mixtureing, irrigation, etc.
  • surface application application, powder coating, coating, etc.
  • immersion poison bait etc.
  • ultra-low volume application method In this method, it is possible to contain 100% of the active ingredient.
  • the agricultural and horticultural pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done.
  • a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve.
  • the compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be prepared separately and mixed at the time of spraying, or both may be used together.
  • the present invention includes such a composition for controlling mixed pests.
  • the mixing ratio (weight ratio) between the compound of the present invention and the active ingredient compound of other pesticides cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, pest type and occurrence, etc. 1: 300 to 300: 1, preferably 1: 100 to 100: 1.
  • the appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 g as the total amount of active ingredient compounds per hectare.
  • the present invention also includes a method for controlling pests by a method for applying such a composition for controlling mixed pests.
  • active ingredient compounds of insecticides, acaricides, nematicides or soil pesticides in the above other pesticides
  • active ingredient compounds include, for example, profenofos , Dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fothiaz , Cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulfophos ( sulprofos), thiometon, bamidthione (vamidot) hion), pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion,
  • Organometallic compounds such as fenbutatin oxide and cyhexatin; Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucytrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin (Tetramethrin), resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermet hrin), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tral
  • Pyridine compounds such as pyridalyl and flonicamid; Cyclic ketoenol compounds such as spirodiclofen, spiromesifen, spirotetramat; Strobilurin-based compounds such as fluacrypyrim; Pyrimidinamine compounds such as flufenerim; Dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; and other compounds such as buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen ), Triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone
  • Microbial pesticides such as: avermectin, emamectin-benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin, spinetoram; natural products such as azadirachtin, rotenone; repellents such as deet; Etc. It is.
  • an active ingredient compound for example, mepanipyrim, pyrimethanil, cyprodinil Anilinopyrimidine compounds such as (cyprodinil); Such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl)-[1,2,4] triazolo [1,5-a] pyrimidine Triazolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole
  • Quinoxaline compounds such as quinomethionate; Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram; Organochlorine compounds such as fthalide, chlorothalonil, quintozene; Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid; Cyanoacetamide compounds such as cymoxanil; Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Fluralaxyl, cyprofuram, carboxyxin, oxycarboxin, thifluzamide, boscalid, isothianil, bix
  • Sulfamide-type compounds such as dichlofluanid; Copper-based compounds such as cupric hydroxide and oxine copper; Isoxazole compounds such as hymexazol; Fosetyl aluminum (fosetyl-Al), tolclofos-methyl, edifenphos, iprobenfos, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum Organophosphorus compounds such as ethyl hydrogen phosphonate; Phthalimide compounds such as captan, captafol, folpet; Dicarboximide compounds such as procymidone, iprodione, vinclozolin;
  • Benzanilide compounds such as flutolanil and mepronil; Penthiopyrad, 3- (difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9RS) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl ]
  • Amido compounds such as a mixture of two anti-isomers of (, 4-methanonaphthalen-5-yl] pyrazole-4-carboxamide (isopyrazam), silthiopham, fenoxanil; Benzamide compounds such as fluopyram and zoxamid; Piperazine compounds such as triforine; Pyridine compounds such as pyrifenox; Car
  • Organotin compounds such as fentin hydroxide and fentin acetate; Urea-based compounds such as pencycuron; Synamic acid compounds such as dimethomorph, flumorph; Phenyl carbamate compounds such as dietofencarb; Cyanopyrrole compounds such as fludioxonil and fenpiclonil; Azoxystrobin, kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin-based compounds such as pyraclostrobin, fluoxastrobin;
  • Oxazolidinone compounds such as famoxadone; Thiazole carboxamide compounds such as ethaboxam; Valinamide compounds such as iprovalicarb, benchthiavalicarb-isopropyl; Acylamino acid compounds such as methyl N- (isopropoxycarbonyl) -L-valyl- (3RS) -3- (4-chlorophenyl) - ⁇ -valaniphenate; Imidazolinone compounds such as fenamidone; Hydroxyanilide compounds such as fenhexamid; Benzenesulfonamide compounds such as flusulfamide; Oxime ether compounds such as cyflufenamid; Anthraquinone compounds; Crotonic acid compounds; Antibiotics such as validamycin, kasugamycin, polyoxins; Guanidine compounds such as iminoctadine and dodine; Quinoline compounds such as 6-tert-butyl-8-fluoro-2,3
  • Other compounds include isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, and metam sodium salt. metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom, pyriofenone, pyribencarb, mandipropamide, mandipropamide (mandipropamide) (fluopicolide), carpropamid, meptyldinocap, ferimzone, spiroxamine, S-2188 (fenpyrazamine), S-2200, ZF-9646, BCF-051, BCM-061 , BCM-062;
  • agrochemicals that can be used in combination with or combined with the compounds of the present invention include, for example, active compound compounds of herbicides such as those described in The Pesticide Manual (15th edition), particularly those of soil treatment type. There is.
  • animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). , Vascular, subcutaneous, lymphoid tissue, etc.) are effective in controlling endoparasites, and in particular, are effective in controlling ectoparasites.
  • ectoparasites examples include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.
  • the animal parasitic mites for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H.
  • kitaokai Haemaphysalis kitaokai
  • Iyasuchimadani Haemaphysalis ias
  • Ixodes ovatus Ixodes ovatus
  • I. nipponensis Ixodes nipponensis
  • Schulze ticks Ixodes persulcatus
  • Takasago testudinarium Amblyomma testudinarium
  • Ootogechimadani Haemaphysalis megaspinosa
  • tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutromb
  • chiggers such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres
  • animal parasitic fleas include ectoparasite worms belonging to the order Flea ( Siphonaptera ), and more specifically, fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ), and the like.
  • fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mouse minnow ( Nosopsyllus fasciatus ), and Yamamoto mouse ( Monopsyllus anisus );
  • the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, particularly dog fleas and cat fleas.
  • ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, .
  • endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke such as liver cirrhosis; coccidium, malaria parasite, intestinal granulocyst, toxoplasma Protozoa such as Ptosporidium, and the like.
  • nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms
  • Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms
  • Japanese schistosomiasis fluke such as liver cirrhosis
  • Examples of host animals include various pet animals, livestock, poultry, etc., and more specifically dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc.
  • the animal parasite control agent containing the compound of the present invention is effective for controlling pests parasitic on pet animals or livestock, particularly ectoparasites.
  • pet animals or domestic animals it is particularly effective for dogs, cats, cows or horses.
  • the compound of the present invention When used as an animal parasite control agent, it may be used as it is, and together with suitable adjuvants, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions, It can also be used in various forms such as an oily suspension.
  • suitable adjuvants powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions, It can also be used in various forms such as an oily suspension.
  • any preparation forms used in the normal field can be used as long as the object of the present invention is met.
  • the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the aforementioned preparation adjuvants for agricultural and horticultural pesticides; positive agents such as cetyltrimethylammonium bromide.
  • Ionic surfactants water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, Ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl Solvents such as ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; oxidations such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Inhibitors; Film
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also
  • the compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • Administration of the compound of the present invention to the host animal is performed orally or parenterally.
  • the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention.
  • the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on A method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.
  • the dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually a ratio of 0.01 mg to 100 g, preferably 0.1 mg to 10 g, per 1 kg body weight of the host animal. Is suitable for administration.
  • the present invention includes a method for controlling pests according to the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.
  • the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.
  • the compound of the present invention When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, It can be mixed with or used in combination with preservatives and the like. Also, if necessary, mix or use with other animal drugs and pesticides such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a more excellent effect may be exhibited.
  • the present invention includes a composition for controlling mixed pests in which various components as described above are mixed or used together, and a method for controlling pests using the composition, particularly a method for controlling ectoparasites or endoparasites. Is also included.
  • the ratio (/) of the eluent used in silica gel column chromatography in the synthesis examples is a volume ratio.
  • Synthesis example 1 Synthesis of 5- [2-chloro-4- (trifluoromethyl) phenyl] -7- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine (Compound No. 81) (1) To a mixed solution of 6.58 g of 6-chloro-4- (trifluoromethyl) pyridin-2-amine and 50 mL of 1,4-dioxane, 4.69 g of ethoxycarbonyl isothiocyanate was added and stirred at 80 ° C. for 3 hours.
  • Table 1 Representative examples of the compounds of formula (I) are listed in Table 1 (Tables 1 to 4). These compounds can be produced on the basis of various production methods of the synthesis example 1 or the compound of the present invention described above.
  • Table 1 No. indicates compound No., Me indicates methyl, c-Pr indicates cyclopropyl, i-Pr indicates isopropyl, Ph indicates phenyl, and the temperature indicated as a physical property is a melting point. .
  • Test Example 3 Effect test on silver leaf whitefly A potted cucumber seedling infested with silver leaf whitefly 1-2 instar larvae was sprayed with a chemical solution adjusted to a concentration of 200 ppm of the compound of the present invention using a hand spray. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Seven days after the treatment, the number of old larvae was examined, and the control value (%) was determined by the following formula. When said compound No. 66, 75, 81 and 90 were tested, all the compounds showed the control value of 80% or more.
  • Control value (%) (1 ⁇ (Ta ⁇ Cb) / (Tb ⁇ Ca)) ⁇ 100
  • Ta old larvae after treatment in treated cucumber seedlings
  • Tb Number of 1-2 instar larvae before treatment in treated cucumber seedlings
  • Ca number of old larvae after treatment in untreated cucumber seedlings
  • Cb Number of 1-2 instar larvae before treatment in untreated cucumber seedlings
  • Test Example 4 Medicinal Efficacy Test Using Dogs against Phytophyllum Tick
  • a dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of the present invention.
  • about 50 young mites were collected from the ear of the dog. Let go through and artificially infest. After the treatment, observe the number of infestations, the number of drops, and the life and death of the fallen spider mites. As a result, the compound of the present invention drops or kills the parasitic spider mite.
  • Test Example 5 Medicinal Efficacy Test Using a Dog against a Cat Flea
  • a gelatin capsule containing 10 mg / kg body weight of the compound of the present invention was administered to a dog (beagle, 8 months old), and immediately after that about 100 cat flea non-blood-sucking adults were covered in the back Let go on and let it infest. After the treatment, collect the cat fleas using a flea removal comb and count the number of fixings. As a result, the compound of the present invention suppresses cat flea infestation.
  • Formulation Example 1 (1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalenesulfonate 2 parts by weight or more To make a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) 60 parts by weight of talc (3) 34.5 parts by weight of calcium carbonate (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.
  • Formulation Example 3 (1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the compound of the present invention Mix at a weight ratio of 4: 1 to make a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.
  • Formulation Example 7 (1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).
  • Formulation Example 8 (1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.
  • Formulation Example 9 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain a liquid agent.
  • the pest control agent comprising the triazolopyridine derivative of the present invention or a salt thereof as an active ingredient has a very high control effect against pests at a low dosage, and various pests that are problematic in the field of agriculture and horticulture, It is possible to control pests parasitizing animals, and is extremely useful, such as having safety against crops, natural enemies of pests or mammals.
  • the entire contents of the description, claims, and abstract of Japanese Patent Application No. 2010-010557 filed on January 21, 2010 are incorporated herein as the disclosure of the specification of the present invention. Is.

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Abstract

Agent de lutte contre un organisme nocif comprenant un nouveau dérivé de triazolopyridine ou un sel de cette dernière comme principe actif. Plus spécifiquement, l'invention concerne un agent de lutte contre un organisme nocif comprenant, comme principe actif, un dérivé de triazolopyridine représenté par la formule suivante (I) [dans laquelle Cy représente un groupe aryle substitué par X ou un groupe hétéroaryle substitué par X; Q représente un atome d'hydrogène, un groupe alkyle pouvant être substitué par A, un groupe cycloalkyle pouvant être substitué par U, un alcényle pouvant être substitué par A, un groupe alkynyle pouvant être substitué par A, un atome d'halogène, un groupe cyano, un groupe aryle, un groupe hétérocyclique pouvant être substitué par un groupe alkyle, CH=NOR2, CH=NNR4R5, COR2, COOR2, OR2, S(O)nR3, ou CONR4R5 ;R1 représente un atome d'hydrogène, un groupe alkyle pouvant être substitué par U, un groupe alcényle pouvant être substitué par A, un groupe cycloalkyle pouvant être substitué par U, un groupe alcényle pouvant être substitué par A, un groupe alkynyle pouvant être substitué par A, un atome d'halogène, un groupe cyano, un groupe aryle, un groupe hétérocyclique pouvant être substitué par un groupe alkyle, CH=NOR2, CH=NNR4R5, COR2, COOR2, OR2, S(O)nR3, NR4R5, ou CONR4R5] ou bien un sel de cette dernière.
PCT/JP2011/051001 2010-01-21 2011-01-20 Dérivé de triazolopyridine ou sel de cette dernière et son utilisation dans un agent de lutte contre un organisme nocif Ceased WO2011090127A1 (fr)

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CN106715428B (zh) * 2014-09-16 2020-07-07 先正达参股股份有限公司 具有含硫取代基的杀有害生物活性四环衍生物
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CN107531698B (zh) * 2015-03-18 2024-08-13 武田药品工业株式会社 具有作为phd抑制剂的活性的稠合双环杂芳基衍生物
KR102609431B1 (ko) 2015-03-18 2023-12-04 다케다 야쿠힌 고교 가부시키가이샤 Phd 저해제로서의 활성을 갖는 융합된 바이시클릭 헤테로아릴 유도체
US10287286B2 (en) 2015-03-18 2019-05-14 Takeda Pharmaceutical Company Limited Compounds
EA035739B1 (ru) * 2015-03-18 2020-08-03 Такеда Фармасьютикал Компани Лимитед Конденсированные бициклические гетероарильные производные с активностью ингибиторов пролилгидроксилазы
WO2016148306A1 (fr) * 2015-03-18 2016-09-22 Takeda Pharmaceutical Company Limited Dérivés hétéroaryles bicycliques fusionnés ayant une activité d'inhibiteurs de phd
EP3328840A1 (fr) 2015-07-01 2018-06-06 Merck Sharp & Dohme Corp. Composés bicycliques triazolo substitués en tant qu'inhibiteurs de pde2
WO2017077968A1 (fr) * 2015-11-05 2017-05-11 住友化学株式会社 Composé hétérocyclique condensé
US10709133B2 (en) 2015-11-05 2020-07-14 Sumitomo Chemical Company, Limited Condensed heterocyclic compound
CN108349970B (zh) * 2015-11-05 2021-03-05 住友化学株式会社 稠合杂环化合物
JPWO2017077968A1 (ja) * 2015-11-05 2018-08-30 住友化学株式会社 縮合複素環化合物
CN108349970A (zh) * 2015-11-05 2018-07-31 住友化学株式会社 稠合杂环化合物
WO2022003510A1 (fr) * 2020-06-29 2022-01-06 Oat & Iil India Laboratories Private Limited Composés triazolopyridine utiles en tant que pesticides

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