WO2017043341A1 - Composé de triazole - Google Patents

Composé de triazole Download PDF

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Publication number
WO2017043341A1
WO2017043341A1 PCT/JP2016/075024 JP2016075024W WO2017043341A1 WO 2017043341 A1 WO2017043341 A1 WO 2017043341A1 JP 2016075024 W JP2016075024 W JP 2016075024W WO 2017043341 A1 WO2017043341 A1 WO 2017043341A1
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WO
WIPO (PCT)
Prior art keywords
compound
mixture
formula
water
reaction
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PCT/JP2016/075024
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English (en)
Japanese (ja)
Inventor
悟 宇治田
和也 植木
和恭 谷
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住友化学株式会社
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Publication of WO2017043341A1 publication Critical patent/WO2017043341A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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

Definitions

  • the present invention relates to an intermediate for producing a compound having pest control activity and a method for producing the same.
  • WO2013 / 018928 describes compounds having pest control activity.
  • the present invention has the formula (6) having an excellent control effect against pests:
  • a production intermediate of a compound represented by formula (hereinafter referred to as compound (6)) and a method for producing compound (6) are provided.
  • the compound (6) has an excellent control effect against pests, and in the production thereof, the compound (6):
  • compound (5) (Hereinafter referred to as compound (5)) is useful as a production intermediate of compound (6).
  • Compound (6) can be produced by the following method. That is, the compound (6) is obtained in the step (A2): Formula (II-3)
  • a step of obtaining a compound (5) by reacting with the compound represented by formula (B2) It is produced by a step of obtaining a compound (6) by intramolecular condensation of the compound (5) in the presence of an acid.
  • the following method can be used to prepare the compound (II-3).
  • Compound II-2 (Hereinafter referred to as Compound II-2). Furthermore, the present invention provides compound (II-3) which is a production intermediate of compound (6).
  • step (A2) will be described.
  • the reaction of compound (II-3) with 1H-1,2,4-triazole is usually carried out in a solvent.
  • the solvent include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane; Halogenated aromatic hydrocarbons; aromatic hydrocarbons such as toluene, benzene and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone Aprotic polar solvents such as N, N-dimethylformamide, N-methyl-2-pyrrolidone, 1,3-dimethyl-2
  • Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkaline earth metal hydrides such as calcium hydride; alkali metal carbonates such as sodium carbonate and potassium carbonate; and triethylamine; Organic bases such as diisopropylpyramine, pyridine, 4-dimethylaminopyridine and the like can be mentioned.
  • 1H-1,2,4-triazole is usually used at a ratio of 1 to 2 moles and a base is usually used at a ratio of 1 to 5 moles relative to 1 mole of compound (II-3).
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction mixture After completion of the reaction, for example, the reaction mixture is mixed with water and then extracted with an organic solvent, and the resulting organic layer is concentrated; the solid produced by mixing the reaction mixture with water is collected by filtration, or Compound (5) can be isolated by collecting the solid produced in the reaction mixture by filtration.
  • the isolated compound (5) can be further purified by recrystallization, chromatography or the like.
  • step (B2) will be described.
  • the reaction for intramolecular condensation of compound (5) in the presence of an acid is usually performed in a solvent.
  • the solvent include water; 2-butanol, ethylene glycol (ethane-1,2-diol), propylene glycol (1,2-propanediol), dipropylene glycol (4-oxa-2,6-heptanediol, 2 -(2-hydroxy-propoxy) -propan-1-ol and a mixture of 2- (2-hydroxy-1-methyl-ethoxy) -propan-1-ol), 1,3-butylene glycol, glycerin, polyethylene glycol ( For example, alcohols having an average molecular weight of 200 to 400); ketones such as methyl isobutyl ketone and cyclohexanone; ethers such as 1,4-dioxane and diethylene glycol dimethyl ether (ie, diglyme); halogenated aromatic hydrocarbons such as chlorobenzene ; Toluene,
  • Examples of the acid include sulfonic acids such as paratoluenesulfonic acid, carboxylic acids such as lactic acid and acetic acid, sulfuric acid, and polyphosphoric acid.
  • the acid is usually used at a ratio of 0.1 to 5 moles relative to 1 mole of the compound (5).
  • the acid when the acid is a liquid such as lactic acid or acetic acid, the acid may be used as a solvent, and the amount used is usually 1 to 5 parts by weight per 1 part by weight of the compound (5). .
  • the reaction temperature is usually in the range of 100 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • reaction mixture and water are mixed and then the organic layer obtained by organic solvent extraction is concentrated, the solid produced by mixing the reaction mixture and water is collected by filtration, or Compound (6) can be isolated by collecting the solid produced in the reaction mixture by filtration.
  • the isolated compound (6) can be further purified by recrystallization, chromatography or the like.
  • step (C2) will be described.
  • chlorinating agent examples include thionyl chloride, phosphorus oxychloride, and phosphorus pentachloride.
  • the chlorinating agent is usually used at a ratio of 1 to 1.5 mol per 1 mol of compound (II-1).
  • the reaction temperature is usually in the range of 20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the reaction is usually performed in a solvent.
  • the solvent include ethers such as 1,4-dioxane, tetrahydrofuran and tert-butyl methyl ether; halogenated aromatic hydrocarbons such as chlorobenzene; aromatic hydrocarbons such as toluene, benzene and xylene; Nitriles and mixtures thereof are mentioned.
  • the reaction is usually performed in a solvent.
  • the solvent include ethers such as 1,4-dioxane, tetrahydrofuran and tert-butyl methyl ether; halogenated aromatic hydrocarbons such as chlorobenzene; aromatic hydrocarbons such as toluene, benzene and xylene; Nitriles and mixtures thereof are mentioned.
  • a base may be added, and examples of the base include organic bases such as triethylamine, diisopropylpyrroleamine, pyridine, 4-dimethylaminopyridine and the like.
  • compound (II-2) is usually used in a proportion of 0.9 to 2 mol and base is usually used in a proportion of 0.9 to 5 mol with respect to 1 mol of compound (II-1).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • reaction mixture and water are mixed and then the organic layer obtained by organic solvent extraction is concentrated, the solid produced by mixing the reaction mixture and water is collected by filtration, or Compound (II-3) can be isolated by collecting the solid produced in the reaction mixture by filtration.
  • the isolated compound (II-3) can be further purified by recrystallization, chromatography or the like.
  • reaction mixture containing compound (II-3) may be directly subjected to the next reaction.
  • Compound (6) can be used as a pest control active ingredient.
  • Pests for which the compound (6) is effective include harmful arthropods and harmful linear animals.
  • Examples of harmful arthropods include, for example, green planthoppers (Nilaparvata lugens), cotton aphids (Aphis gossypii), and whitefly insects (Bemisia tabaci); Lepidoptera: Musca domestica, Diptera pests such as Culex pipiens pallens; Kibuli Lepidoptera, and the like.
  • Examples of harmful linear animals include nematodes such as sweet potato nematode (Meloidogyne incognita), soybean cyst nematode (Heterodera glycines), and wheat nematode nematode (Pratylenchus neglectus).
  • nematodes such as sweet potato nematode (Meloidogyne incognita), soybean cyst nematode (Heterodera glycines), and wheat nematode nematode (Pratylenchus neglectus).
  • the compound (6) is usually mixed with an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier and used as a pest control agent.
  • an inert carrier such as a solid carrier, a liquid carrier or a gaseous carrier
  • the pest control agent usually contains 0.01 to 95% by weight of the compound (6).
  • Such pest control agents may be added with surfactants and other formulation adjuvants as necessary, to emulsions, oils, powders, dry flowables, fine granules, granules, wettable powders, aqueous solvents, flowables. It is formulated into agents, microcapsules, aerosols, smoke agents, poison baits, resin preparations, shampoos, paste preparations, foams, carbon dioxide preparations, tablets and the like. These preparations can be further used after being processed into mosquito coils, electric mosquito repellent mats, liquid mosquito repellent preparations, fumigants, fumigants, sheet preparations, spot-on agents, and oral treatment agents.
  • solid carriers examples include clays (kaolin clay, bentonite, etc.), inorganic minerals (activated carbon, calcium carbonate, etc.), and synthetic resins (polyester resins such as polypropylene, nylon resins such as nylon-6, polyamide resins, vinyl chloride) -Propylene copolymer, etc.).
  • liquid carrier examples include water, alcohols (isopropyl alcohol, butanol, benzyl alcohol, ethylene glycol, propylene glycol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, Methylnaphthalene), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), Ethers (diisopropyl ether, 1,4-dioxane, diethylene glycol dimethyl ether, etc.), acid amides (N, N-dimethylformamide, N, N-dimethylace
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • formulation adjuvants include sticking agents, dispersants, colorants, antifreezes and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin Derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), glycerin, BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4-) And a mixture of methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • sticking agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin Derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), glycerin, BHT (2,6-di
  • the pest control agent containing the compound (6) is applied directly to pests and / or applied to pest habitats (plants, soil, households, animal bodies, etc.) to control pests. can do.
  • the application amount is usually 1 to 10,000 g in the amount of the compound (6) per 10,000 m 2 .
  • the amount applied is the amount of the compound (6) per 1 m 2 of area when applied on the surface. Usually 0.01 to 1.000 mg, and when applied to a space, the amount of compound (6) per 1 m 3 of space is usually 0.01 to 500 mg.
  • the pest control agent containing compound (6) When the pest control agent containing compound (6) is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the compound (6) is 0.1 to 10,000 ppm. Apply granules, powders, oils, aerosols, smoke, poison baits, etc. as they are.
  • High performance liquid chromatography analysis condition 1 Internal standard substance: biphenyl mobile phase: A solution: 0.1% phosphoric acid aqueous solution, B solution: acetonitrile gradient condition: Table 1 below Column: SUMPAX® ODS Z-CLUE, particle size 3.0 ⁇ m, 3.0 mm I.D. D. ⁇ 100mm UV measurement wavelength: 254 nm Flow rate: 1.0 mL / min Column oven: 40 ° C Injection volume: 10 ⁇ L ⁇ Gradient condition>
  • the obtained mixture was dropped into a mixture of 22.5 g of compound (II-2), 12.28 g of triethylamine and 46.55 g of xylene over 3 hours at an internal temperature of 30 ° C., and stirred at an internal temperature of 30 ° C. for 1 hour. . Thereafter, the reaction mixture was heated to an internal temperature of 60 ° C., 32.0 g of N, N-dimethylformamide was added and stirred for 1 hour, and then cooled to room temperature to obtain 155.61 g of a solution.
  • Example 2 155.61 g of the solution obtained in Example 2 was added dropwise to a mixture of 38.51 g of potassium carbonate, 11.50 g of 1H-1,2,4-triazole and 46.65 g of xylene at an internal temperature of 60 ° C. over 20 minutes, The mixture was stirred at an internal temperature of 60 ° C. for 23 hours. Subsequently, after a part of the solvent was distilled off under reduced pressure, the pressure was returned to normal pressure, water was added, and the solvent was distilled off again under reduced pressure to precipitate a solid. Water distilled azeotropically was returned to the reaction vessel.
  • Example 1 To a mixture of 8.31 g of potassium carbonate and 2.50 g of 1H-1,2,4-triazole, 10.0 g of N, N-dimethylformamide was added and stirred, and the crude compound obtained in Example 1 ( II-3) A mixture of 16.7 g (content 60%) and 9.5 g of N, N-dimethylformamide was added dropwise at an internal temperature of 53 ° C. over 1.5 hours, and then the internal temperature was raised to 60 ° C. And stirred for 12.5 hours. To the resulting reaction mixture, 30.0 g of methyl isobutyl ketone and 30.0 g of water were sequentially added dropwise, followed by extraction with methyl isobutyl ketone.
  • Example 8 To a mixture of 3.33 g of compound (5) and 4.45 g of N, N-dimethylacetamide, 3.20 g of 52.3% sulfuric acid was added dropwise and stirred for 22 hours while heating in a bath at 107 ° C.
  • Example 9 A mixture of 4.55 g of compound (5), 0.94 g of paratoluenesulfonic acid monohydrate and 18.5 g of xylene was stirred at an internal temperature of 140 ° C. for 37 hours.
  • Example 10 A mixture of 101 mg of compound (5) and 405 mg of acetic acid was stirred at an internal temperature of 100 ° C. for 16 hours. When this reaction mixture was analyzed by the area percentage method using high performance liquid chromatography (high performance liquid chromatography analysis condition 1), the ratio of compound (6) was 98.9 area%.
  • Example 11 A mixture of 101 mg of compound (5) and 405 mg of acetic acid was stirred at an internal temperature of 100 ° C. for 16 hours. When this reaction mixture was analyzed by the area percentage method using high performance liquid chromatography (high performance liquid chromatography analysis condition 1), the ratio of compound (6) was 98.9 area%.
  • Formulation Example 1 A flowable agent was prepared by mixing 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of compound (6) and 55 parts of water and finely pulverizing them by a wet pulverization method. obtain. Test example 1 The preparation of the compound (6) obtained in Preparation Example 1 was diluted with water so that the concentration became 200 ppm to obtain a diluted solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Cb number of insects before treatment in the untreated group
  • Cai number of live parasites when observed in the untreated group
  • Tb number of insects before treatment in the treated group
  • Tai number of live parasitic insects during observation of the treated group
  • the group means a group in which a preparation diluted with the same amount of water as the treatment group was sprayed on the preparation not containing the compound (6) in Preparation Example 1.
  • Test example 2 The preparation of the compound (6) obtained in Preparation Example 1 was diluted with water so that the concentration became 200 ppm to obtain a diluted solution.
  • apples were planted in plastic cups and grown until the seventh and eighth true leaves developed.
  • the diluted solution was sprayed on the apple at a rate of 20 mL / cup. After spraying, the plants were air-dried, and 60 first-instar larvae of Adoxyphys orana fascita were released, the bottom was hollowed out, and the plastic cup with filter paper was placed in an inverted position. Seven days later, the number of dead insects was counted, and the death rate was calculated from the following formula.
  • a filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the diluted solution was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food.
  • Ten female fly (Musca domestica) females were released into the polyethylene cup and covered. After 24 hours, the life and death of the house fly was investigated, the number of dead insects was counted, and the death rate was calculated by the following formula.
  • a filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the diluted solution was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food.
  • Two adult male cockroaches (Blatella germanica) were released into the polyethylene cup and covered. Six days later, the death and death of German cockroaches were investigated, the number of dead insects was counted, and the death rate was calculated according to the following formula.
  • 0.7 ml of the diluted solution was added to 100 ml of ion-exchanged water (active ingredient concentration: 3.5 ppm). Twenty dead larvae of Culex pipiens pallens were released into the solution, and the number of dead worms was counted one day later to determine the mortality rate.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 95% or more.
  • Test Example 6 2 mg of compound (6) was weighed into a screw tube (Marem No. 5; 27 ⁇ 55 mm), 0.2 mL of acetone was added, and the mixture was covered and dissolved. The screw tube was rotated and inverted to coat the solution so that the entire inner wall was uniform. After removing the lid and allowing it to air dry for about 2 hours, 5 groups of non-blood-sucking young ticks (Haemaphysalis longicornis) were released and covered. Two days later, the number of dead insects was counted, and the death rate was calculated by the following formula.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 60% or more.
  • Test Example 7 Compound (6) was dissolved in acetone to prepare a 10% w / v acetone solution.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 100%.
  • the present invention provides a production intermediate of compound (6) having pesticidal activity and a production method thereof.

Abstract

Cette invention concerne un composé représenté par la formule (6) ayant un excellent effet sur la lutte contre les nuisibles qui peut être produit par une étape d'obtention d'un composé représenté par la formule (5) par réaction d'un composé représenté par la formule (II-3) avec un 1H-1,2,4-triazole en présence d'une base et une étape d'obtention d'un composé représenté par la formule (6) par condensation intramoléculaire du composé représenté par la formule (5) en présence d'un acide.
PCT/JP2016/075024 2015-09-08 2016-08-26 Composé de triazole WO2017043341A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-176950 2015-09-08
JP2015176950 2015-09-08

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WO2017043341A1 true WO2017043341A1 (fr) 2017-03-16

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019013273A1 (fr) * 2017-07-13 2019-01-17 住友化学株式会社 Composé hétérocyclique, et agent de lutte contre des arthropodes nuisibles comprenant celui-ci
WO2020058010A1 (fr) 2018-09-19 2020-03-26 Basf Se Mélanges pesticides comprenant un composé mésoionique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009156484A2 (fr) * 2008-06-27 2009-12-30 Novartis Ag Composés organiques
WO2013018928A1 (fr) * 2011-08-04 2013-02-07 Sumitomo Chemical Company, Limited Composé hétérocyclique condensé et utilisation de celui-ci pour la lutte contre les organismes nuisibles
WO2015133603A1 (fr) * 2014-03-07 2015-09-11 住友化学株式会社 Composé hétérocyclique condensé et son utilisation pour lutter contre les ravageurs

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009156484A2 (fr) * 2008-06-27 2009-12-30 Novartis Ag Composés organiques
WO2013018928A1 (fr) * 2011-08-04 2013-02-07 Sumitomo Chemical Company, Limited Composé hétérocyclique condensé et utilisation de celui-ci pour la lutte contre les organismes nuisibles
WO2015133603A1 (fr) * 2014-03-07 2015-09-11 住友化学株式会社 Composé hétérocyclique condensé et son utilisation pour lutter contre les ravageurs

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019013273A1 (fr) * 2017-07-13 2019-01-17 住友化学株式会社 Composé hétérocyclique, et agent de lutte contre des arthropodes nuisibles comprenant celui-ci
CN110914264A (zh) * 2017-07-13 2020-03-24 住友化学株式会社 杂环化合物及含有其的有害节肢动物防治剂
JPWO2019013273A1 (ja) * 2017-07-13 2020-05-07 住友化学株式会社 複素環化合物及びそれを含有する有害節足動物防除剤
US11203590B2 (en) 2017-07-13 2021-12-21 Sumitomo Chemical Company, Limited Heterocyclic compound and harmful-arthropod control agent containing same
CN110914264B (zh) * 2017-07-13 2022-02-11 住友化学株式会社 杂环化合物及含有其的有害节肢动物防治剂
JP7082978B2 (ja) 2017-07-13 2022-06-09 住友化学株式会社 複素環化合物及びそれを含有する有害節足動物防除剤
WO2020058010A1 (fr) 2018-09-19 2020-03-26 Basf Se Mélanges pesticides comprenant un composé mésoionique

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