WO2017222037A1 - Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif - Google Patents

Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif Download PDF

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WO2017222037A1
WO2017222037A1 PCT/JP2017/023128 JP2017023128W WO2017222037A1 WO 2017222037 A1 WO2017222037 A1 WO 2017222037A1 JP 2017023128 W JP2017023128 W JP 2017023128W WO 2017222037 A1 WO2017222037 A1 WO 2017222037A1
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compound
alkyl
salt
alkylthio
alkylcarbonyl
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PCT/JP2017/023128
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English (en)
Japanese (ja)
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哲夫 米田
幸太郎 吉田
優太 田澤
達也 可児
洋子 長
明史 能島
勇斗 村井
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石原産業株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides

Definitions

  • the present invention relates to a novel N- (4-pyridyl) benzamide compound or a salt thereof, a pest control agent containing them as an active ingredient, and a method for controlling pests by applying an effective amount thereof.
  • Patent Document 1 describes a wide range of arylamide compounds
  • Patent Document 2 describes a compound having a pyridine skeleton for a wide range of pharmaceutical uses.
  • An object of the present invention is to provide a compound having high activity against pests, to provide a pest control agent using the compound, and to provide a method for controlling pests by applying the compound. That is.
  • Patent Documents 1 and 2 do not have a specific description regarding the compound of the present invention.
  • the present inventors have made various studies on pyridine compounds in order to find better pest control agents. As a result, the present inventors have found that a novel N- (4-pyridyl) benzamide compound or a salt thereof has a very high control effect against pests with a low dose, and completed the present invention. That is, the present invention provides a compound of formula (I):
  • R 1 is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, alkylthiohaloalkylthio or pentafluorosulfanyl;
  • R 2 is halogen atom, hydroxyl, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxyalkyl, alkenyloxyalkyl, alkynyl Oxyalkyl, cycloalkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, trialkylsilyl, amino, monoalkylamin
  • the pest control agent comprising the compound of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests at a low dose.
  • the present invention relates to a compound represented by the following formula (I) or a salt thereof (hereinafter sometimes collectively referred to as “the present compound”).
  • the present compound a compound represented by the following formula (I) or a salt thereof (hereinafter sometimes collectively referred to as “the present compound”).
  • C n (n is a natural number) is synonymous with “carbon number n”.
  • ppm is described as the concentration, it indicates ppm by weight.
  • R 1 is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, alkylthiohaloalkylthio or pentafluorosulfanyl
  • R 2 is halogen atom, hydroxyl, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxyalkyl, alkenyloxyalkyl, alkynyl Oxyalkyl, cycloalkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, trialkylsilyl, amino, monoalkyla
  • halogen atom of the compound of the formula (I) or a salt thereof or the halogen as a substituent examples include each atom of fluorine, chlorine, bromine or iodine.
  • 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 or alkyl moiety of the compound of the formula (I) or a salt thereof examples include, for example, methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, isopentyl, neopentyl, normal hexyl.
  • linear or branched C 1 -C 6 groups such as neohexyl.
  • alkenyl or alkenyl moiety of the compound of formula (I) or a salt thereof examples include, for example, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, -Methyl-2-propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl, 2,3 And straight-chain or branched C 2 -C 6 groups such as -dimethyl-2-butenyl.
  • alkynyl or alkynyl moiety of the compound of the formula (I) or a salt thereof examples include, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, Linear or branched C 2 ⁇ such as 2-methyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl C 6 group may be mentioned.
  • Examples of the cycloalkyl or cycloalkyl part of the compound of the formula (I) or a salt thereof include C 3 -C 6 groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Examples of the aryl or aryl moiety of the compound of the formula (I) or a salt thereof include C 6 -C 10 groups such as phenyl and naphthyl.
  • the salt of the compound of the formula (I) includes any salt as long as it is acceptable in the technical field.
  • inorganic salts such as hydrochloride, perchlorate, sulfate, and nitrate
  • organic acid salts such as acetate, trifluoroacetate, oxalate, p-toluenesulfonate, and methanesulfonate.
  • the compound of the formula (I) or a salt thereof may have an isomer such as an optical isomer, but the present invention includes both isomers and isomer mixtures. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Depending on the type of isomer, there may be a chemical structure different from that of the formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, the scope of the present invention. It is clear that it is within.
  • the compound of the above formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production methods and ordinary salt production methods, but is not limited to these methods. Absent.
  • the compound of the above formula (I) can be produced by reacting a compound represented by the following formula (II) with a compound represented by the following formula (III) in the presence of a dehydration condensing agent.
  • the compound of Formula (II) can also be manufactured by a well-known method besides using a commercial item.
  • the compound of Formula (III) can use a commercial item, and can also manufacture it by the method as described in a postscript intermediate manufacturing method.
  • Examples of the dehydrating condensing agent include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.
  • the reaction can be performed by adding an additive as necessary.
  • Examples of the additive include 1-hydroxybenzotriazole, N-hydroxysuccinimide, N, N-dimethyl-4-aminopyridine and the like.
  • the reaction can be carried out in the presence of a base as necessary.
  • a base include tertiary amines such as triethylamine, 4-methylmorpholine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] -7-undecene, pyridine, 4- (dimethylamino) pyridine, 2 , 6-lutidine and the like.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited, but for example, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone; ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane; nitrogen-containing compounds such as pyridine
  • acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • nitrogen-containing compounds such as pyridine
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of the formula (I) can be produced by reacting a compound represented by the following formula (II-a) with a compound represented by the following formula (III) in the presence of a base.
  • the compound of the formula (II-a) can be a commercially available product or can be produced by the method described in the intermediate production method described later.
  • R 1 , R 2 , R 3 , R 4 and m are as described above;
  • X is a halogen atom.
  • Examples of the halogen atom that is X include fluorine, chlorine, bromine, and iodine atoms.
  • the base may be an organic base or an inorganic base.
  • the organic base include amine bases such as triethylamine and diisopropylethylamine.
  • examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane; acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone; dichloromethane and chloroform 1 type, or 2 or more types can be appropriately selected and used from such aliphatic halogenated hydrocarbons.
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound represented by the following formula (Ib) in which R 3 is the following R 3a is represented by the following formula (Ia) when R 3 is a hydrogen atom. It can be produced by reacting a compound with a compound represented by the formula: R 3a X in the presence of a base.
  • R 3a is alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl or arylcarbonyl; R 1 , R 2 , R 4 , X and m Is as described above.
  • Examples of the base include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide. Thing; etc. are mentioned.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane; acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone; dichloromethane and chloroform 1 type, or 2 or more types can be appropriately selected and used from such aliphatic halogenated hydrocarbons.
  • the reaction temperature can be usually in the range of about 20 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time can usually be from several minutes to 48 hours.
  • the compound of the formula (II-a) can be produced by reacting the compound of the formula (II) with a halogenating agent as shown in the following scheme.
  • halogenating agent examples include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus pentachloride and the like.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited, but for example, one or two or more types of aliphatic halogenated hydrocarbons such as methylene chloride, dichloroethane, and chloroform; aromatic hydrocarbons such as toluene and chlorobenzene, and the like are appropriately selected. Can do.
  • the reaction temperature can be usually from about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of the formula (III) can be produced by reacting a compound represented by the following formula (IV) with a compound represented by the following formula (V).
  • the compound of Formula (IV) and the compound of Formula (V) can also be manufactured by a well-known method besides using a commercial item.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent is not particularly limited, but for example, acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone; ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane; nitrogen-containing compounds such as pyridine
  • acid amides such as N, N-dimethylformamide and N-methylpyrrolidinone
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • nitrogen-containing compounds such as pyridine
  • the reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of formula (VII) can be produced by reacting the compound of formula (VI) with ditert-butyl dicarbonate, if necessary, in the presence of a base.
  • a base examples include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
  • alkali metal amides such as lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, and potassium bis (trimethylsilyl) amide.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent examples include, but are not limited to, ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane; esters such as methyl acetate and ethyl acetate; aliphatic halogens such as methylene chloride, dichloroethane and chloroform.
  • ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane
  • esters such as methyl acetate and ethyl acetate
  • aliphatic halogens such as methylene chloride, dichloroethane and chloroform.
  • One kind or two or more kinds can be appropriately selected and mixed from the following: hydrocarbons; alcohols such as methanol, ethanol and tert-butyl alcohol; water;
  • the reaction temperature can usually be in the range of about ⁇ 20 ° C. to the temperature at which the reaction system is heated to reflux.
  • the compound of the formula (VIII) can be produced by reacting the compound of the formula (VII) with a compound represented by the formula: R 3a X in the presence of a base. This reaction can be carried out in the same manner as in the above production method [3].
  • the compound of the formula (III-1) can be produced by reacting the compound of the formula (VIII) with an acid.
  • the acid include inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid and trifluoroacetic acid.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent include, but are not limited to, ethers such as tetrahydrofuran, ethylene glycol dimethyl ether and 1,4-dioxane; esters such as methyl acetate and ethyl acetate; aliphatic halogens such as methylene chloride, dichloroethane and chloroform.
  • reaction temperature can usually be in the range of about 0 ° C. to a temperature at which the inside of the reaction system is heated to reflux.
  • reaction time can usually be from several minutes to 48 hours.
  • the desirable mode of the pest control agent containing the compound of the present invention is described below.
  • Examples of the pest control agent containing the compound of the present invention include pests, mites, nematodes or soil pests that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural insecticides, acaricides, nematicides or Soil-killing pesticides.
  • the compound of the present invention is useful as an active ingredient of agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides.
  • aphids such as peach aphids, cotton aphids Moth, weevil, lotus moth, codling moth, ball worm, cigarette bud worm, gypsy moth, corn borer, chanoco cricket, leafworm, ball weevil, planthopper, leafhopper, scale insect, stink bug, whitefly Pests, such as slugs, cockroaches, house flies, house mosquitoes, etc .; agricultural pests such as slugs, mussels, etc .; Bakuga, azuki beetle, wolfberry, beetle Stored pests such as garments; clothing such as moths, swordfish, termites etc .; house pests; pests such as nymphs, mite spider mites, kanzawa spider mites, man
  • Plant parasitic mites Plant parasitic mites; Indoor dust mites such as Staghorn mite, Salamander mites, Southern mites, etc .; It is effective for controlling pests such as plant parasitic nematodes, etc .;
  • the agricultural and horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. is there. Among them, it is very useful as an insecticide or acaricide because it shows a further excellent effect in controlling plant parasitic mites and agricultural pests.
  • agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides containing the compounds of the present invention are various resistances against drugs such as organophosphorus agents, carbamate agents, synthetic pyrethroid agents, neonicotinoid agents, etc. It is also effective for controlling pests. Furthermore, since the compound of the present invention has an excellent osmotic transfer property, the agricultural or horticultural insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is treated on the soil. By this, it is possible to control pests in the foliage at the same time as the control of soil harmful insects, mites, nematodes, gastropods, and isopods.
  • insecticide acaricide, nematicide or soil insecticide containing the compound of the present invention
  • the above plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods And agricultural and horticultural insecticides, acaricides, nematicides or soil insecticides that comprehensively control soil pests and the like.
  • the pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily suspension by mixing the compound with various agricultural adjuvants. It is used in various forms such as pharmaceuticals, aqueous granules, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc., but as long as it meets the purpose of the present invention, it is usually used in this field. It can be in any formulation form.
  • 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 , 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, etc.
  • 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,
  • Solvent fatty acid salt, benzoate, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, alcohol Sulfate ester salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester, alkyl aryl phosphate, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl
  • 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 and antifungal agents 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, desirably 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 application of the pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application place, type of pests and occurrence, etc., but generally 0.05 to 800,000 ppm
  • the active ingredient concentration is preferably 0.5 to 500,000 ppm
  • 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 includes a method for controlling pests by such an application method, particularly a method for controlling pests, mites, nematodes or soil pests, particularly plant parasitic mites, agricultural pests, plant parasitic nematodes. Also included are methods of controlling the species.
  • the pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc., and in this case, more excellent effects and activities may be exhibited.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. .
  • an insecticidal composition, an acaricidal composition, a nematicidal composition or a composition for soil-killing insect pests in which the compound of the present invention and one or more active ingredient compounds of other agricultural chemicals are mixed or used in combination.
  • the product can improve the application range, the timing of chemical treatment, the control activity, and the like in a preferable direction.
  • the compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately by mixing them at the time of spraying, or both may be used together.
  • the present invention includes such a pest control composition.
  • insect pathogenic fungi Microbial pesticides such as avermectin,
  • an active ingredient compound for example, mepanipyrim, pyrimethanil, cyprodinil ), Anilinopyrimidine compounds such as ferimzone; Tria such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole,
  • an agrochemical that can be used in combination with or combined with the compound of the present invention, for example, an active ingredient compound of a herbicide as described in The Pesticide Manual (15th edition), particularly a soil treatment type, etc. There is.
  • N- (4-pyridyl) benzamide compound or a salt thereof of the present invention will be exemplified, but these do not limit the present invention.
  • R 1 in the halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, Alkoxyhaloalkyl, alkylthio, halo alkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom , Hydroxyl, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkoxyalkyl, alkenyloxyalkyl, alkynyloxyalkyl, cycloalkoxyalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, alkoxyhaloalkyl, alkoxyhaloalkyl , Trialkyls
  • R 1 in formula (I) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio, or pentafluorosulfanyl.
  • R 2 in the formula (I) is a halogen atom, nitro, alkyl, alkoxy, alkylthio, alkylsulfonyl, amino or dialkylamino, or a compound thereof salt.
  • R 3 in the formula (I) is a hydrogen atom, alkyl, cycloalkyl, alkoxyalkyl, alkylcarbonyl or alkoxycarbonyl.
  • R 4 in the formula (I) is a halogen atom, nitro, alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl, alkoxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonylalkoxy
  • R 4 in the formula (I) is a halogen atom, mercapto, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, alkenyloxy, alkynyloxy, haloalkoxy, alkylthio, alkenylthio, alkynylthio, haloalkylthio Alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, haloalkylsulfonyl, alkoxyalkyl, alkylthioalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, hydroxylalkyl, formyl, carboxyl, alkylcarbonyl,
  • R 4 in the formula (I) is a halogen atom, nitro, alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl, alkoxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonylalkoxy 10.
  • the compound or a salt thereof according to any one of (1) to (9), which is carbonyl, cyanoalkoxycarbonyl or (alkylthio) carbonyl.
  • R 4 in the formula (I) is a halogen atom, nitro, alkoxy, alkoxycarbonyl, (alkylthio) carbonyl, monoalkylaminocarbonyl or mono (cycloalkylalkyl) aminocarbonyl Or a salt thereof.
  • R 1 in the formula (I) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom, nitro, alkyl, alkoxy, alkylthio, Alkylsulfonyl, amino or dialkylamino;
  • R 3 is a hydrogen atom, alkyl, cycloalkyl, alkoxyalkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 is a halogen atom, nitro, alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl , Alkoxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonyl
  • R 1 in the formula (I) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom, nitro, alkyl, alkoxy, alkylthio, Alkylsulfonyl, amino or dialkylamino;
  • R 3 is a hydrogen atom, alkyl, cycloalkyl, alkoxyalkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 is a halogen atom, nitro, alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl , Alkoxycarbonyl, alkynyloxycarbonyl, cycloalkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonyl
  • R 1 in the formula (I) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom, nitro, alkyl, alkylthio, alkylsulfonyl Or
  • R 3 is a hydrogen atom, alkyl, cycloalkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 is a halogen atom, nitro, alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl, alkoxycarbonyl, alkynyloxycarbonyl, Cycloalkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonylalkoxycarbonyl, cyanoalkoxycarbonyl,
  • R 1 in the formula (I) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom, nitro, alkyl, alkylthio,
  • R 3 is a hydrogen atom, alkyl, cycloalkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 is a halogen atom, nitro, alkyl, alkoxy, alkylthio, carboxyl, alkylcarbonyl, alkoxycarbonyl, alkynyloxy Carbonyl, cycloalkoxycarbonyl, haloalkoxycarbonyl, alkoxyalkoxycarbonyl, alkoxycarbonylalkoxycarbonyl, cyanoalkoxycarbonyl Or (alkylthio) carbonyloxy; compound
  • R 1 in the formula (I) is a halogen atom, alkyl, haloalkyl, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom, alkyl, alkylthio, alkylsulfonyl or amino
  • R 3 is a hydrogen atom, alkyl, cycloalkyl, alkylcarbonyl or alkoxycarbonyl;
  • R 4 is a halogen atom, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, cyanoalkoxycarbonyl or (alkylthio) carbonyl
  • R 1 in the formula (I) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen atom or alkyl;
  • R 3 is hydrogen
  • R 4 is a halogen atom, nitro, alkoxy, alkoxycarbonyl, (alkylthio) carbonyl, monoalkylaminocarbonyl or mono (cycloalkylalkyl) aminocarbonyl; and (1) or m above wherein m is 0 or 1;
  • the compound or a salt thereof according to (2) is a halogen atom, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyhaloalkyl, haloalkylthio or pentafluorosulfanyl;
  • R 2 is a halogen
  • a pest control agent comprising the compound according to any one of (1) to (16) or a salt thereof as an active ingredient.
  • a method for controlling pests by applying an effective amount of the compound or salt thereof according to any one of (1) to (16).
  • Synthesis example 1 Synthesis of methyl 4- (4- (heptafluoroisopropyl) benzamido) nicotinate (Compound No. I-9) 4- (heptafluoroisopropyl) benzoyl chloride (250 mg, 0.8 mmol), methyl 4-amino-nicotinate ( 123.3 mg, 0.8 mmol) and diisopropylethylamine (0.42 mL, 2.4 mmol) were dissolved in tetrahydrofuran (5 mL) and stirred at 60 ° C. for 1 hour. After allowing to cool to room temperature, water was added and the mixture was extracted with ethyl acetate.
  • Synthesis example 2 Synthesis of methyl 4- (4- (trifluoromethyl) benzamido) nicotinate (Compound No. I-6) 4- (trifluoromethyl) benzoyl chloride (550 mg, 2.6 mmol), methyl 4-amino-nicotinate ( 400 mg, 2.6 mmol) and diisopropylethylamine (1.4 mL, 7.9 mmol) were dissolved in tetrahydrofuran (9 mL) and stirred at 60 ° C. for 1 hour. After allowing to cool to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the solvent was distilled off under reduced pressure to obtain the desired product (490 mg, 57% yield).
  • Synthesis example 3 Synthesis of methyl 4- (N-ethyl-4-((trifluoromethyl) benzamido) nicotinate (Compound No. I-407) methyl 4- (ethylamino) nicotinate (1.0 g, 5.6 mmol), diisopropyl 4- (Trifluoromethyl) benzoyl chloride (1.16 g, 5.6 mmol) was added to a solution of ethylamine (1.94 mL, 11.1 mmol) in tetrahydrofuran (19 mL), and the mixture was stirred for 16 hours at 65 ° C. The reaction mixture was mixed with water.
  • Table 1 typical examples of the compounds of formula (I) according to the present invention are listed in Table 1. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
  • Table 1 the numerical values described in the physical properties column indicate melting points (° C.), and for compounds for which melting points are not described, their 1 H-NMR spectral data are listed in Tables 2 and 3, In the physical property column of the table, NMR is described. No. 1 in Table 1 Indicates a compound number.
  • Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr represents a normal propyl group
  • i-Pr represents an isopropyl group
  • i-Bu represents an isobutyl group
  • t-Bu represents a tertiary butyl group
  • c-Pr represents a cyclopropyl group.
  • Test Example 1 Effect test on green planthopper Rice seedlings were immersed in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. In this, about 10 larvae of 2 to 3 years old were released, and the tube mouth was covered with gauze and allowed to stand in a constant temperature room at 25 ° C. Five days after the treatment, the survival of the brown planthopper was determined, and the death rate (%) was determined by the following formula. As the compound of the present invention, the above-mentioned compound No.
  • Test Example 2 Effect test on tobacco whitefly An adult tobacco whitefly was released on a pot-planted cucumber seedling. After laying eggs for one day, cucumber seedlings were taken out and placed in a constant temperature room with illumination at 25 ° C. Seven days later, the number of 1-2 instar larvae parasitizing the cucumber seedlings was examined, and a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm was sprayed 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. As the compound of the present invention, the above-mentioned compound No.
  • Control value (1 ⁇ (Ta ⁇ Cb) / (Tb ⁇ Ca)) ⁇ 100
  • Ta Number of old larvae after treatment in treated cucumber seedling
  • Tb Number of first to second larvae before treatment in treated cucumber seedling
  • Ca Number of old larvae after treatment in untreated cucumber seedling
  • Cb Before treatment in untreated cucumber seedling Number of larvae 1-2
  • Test Example 3 Effect test on peach aphid
  • Five adult peach aphids were released on radish leaves inserted in test tubes. After removing adults one day later, the number of larvae parasitizing on radish leaves was counted and immersed in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. As the compound of the present invention, the above-mentioned compound No.
  • 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 alkylnaphthalene sulfonate 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) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (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 present compound 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 the above (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 formation).
  • Formulation Example 8 (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.

Abstract

Bien qu'une variété d'agents antiparasitaires a été utilisée pendant de nombreuses années, plusieurs de ces agents antiparasitaires ont divers problèmes, telle qu'une efficacité insuffisante, et une restriction sur leur utilisation en raison d'une résistance acquise par des insectes nuisibles, etc. Le but de la présente invention est de fournir un composé efficace pour un nouvel agent antiparasitaire qui est moins susceptible de présenter un tel inconvénient. La présente invention concerne : Un composé N-(4-pyridyl)benzamide représenté par la formule (I) ou son sel; un agent antiparasitaire contenant le composé ou son un sel en tant qu'ingrédient actif; et un procédé antiparasitaire par l'application d'une quantité efficace du composé ou son sel.
PCT/JP2017/023128 2016-06-24 2017-06-23 Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif WO2017222037A1 (fr)

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AU2018257296B2 (en) * 2017-04-27 2022-01-06 Ishihara Sangyo Kaisha, Ltd. N-(4-pyridyl) nicotinamide compound or salt thereof
WO2022071434A1 (fr) * 2020-09-30 2022-04-07 住友化学株式会社 Composé hétérocyclique et composition de lutte contre les arthropodes nuisibles le contenant

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WO2019163921A1 (fr) * 2018-02-22 2019-08-29 石原産業株式会社 Composé de pyridine substitué et sel de celui-ci
WO2022071434A1 (fr) * 2020-09-30 2022-04-07 住友化学株式会社 Composé hétérocyclique et composition de lutte contre les arthropodes nuisibles le contenant

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