WO2020054712A1 - 有害生物防除剤 - Google Patents

有害生物防除剤 Download PDF

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Publication number
WO2020054712A1
WO2020054712A1 PCT/JP2019/035533 JP2019035533W WO2020054712A1 WO 2020054712 A1 WO2020054712 A1 WO 2020054712A1 JP 2019035533 W JP2019035533 W JP 2019035533W WO 2020054712 A1 WO2020054712 A1 WO 2020054712A1
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Prior art keywords
halo
compound
alkyl
trifluoromethyl
pyridin
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PCT/JP2019/035533
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English (en)
French (fr)
Japanese (ja)
Inventor
慎二 長谷川
翔太郎 上野
大樹 新子
小林　武
拓人 角
周 浅野
忠英 藤田
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日本化薬株式会社
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Priority to JP2020546030A priority Critical patent/JP7399589B2/ja
Publication of WO2020054712A1 publication Critical patent/WO2020054712A1/ja
Priority to JP2023144922A priority patent/JP7682234B2/ja

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/06—Coating or dressing seed
    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • 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
    • 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 a compound represented by the formula (1), the formula (2) or the formula (3) or a salt thereof, or an N-oxide thereof, and a pesticidal composition containing the same as an active ingredient.
  • Patent Documents 1 and 2 disclose a fused heterocyclic compound as a pesticide.
  • Patent Documents 3 and 4 disclose claims containing 2- (pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyridine. It is not actually synthesized, and Patent Document 5 discloses a compound having a certain [1,2,4] triazolo [1,5-a] pyridine ring as a pesticide.
  • Patent Document 6 discloses certain amide compounds. However, a compound having high pest control activity and high practicality has not been found.
  • An object of the present invention is to provide a novel compound exhibiting excellent control activity against various pests and a pest control agent comprising the compound as an active ingredient.
  • the present inventors have found that the compound represented by the formula (1), the formula (2) or the formula (3) has a high pest control activity. Reached.
  • G 1 Is G 1 -1, G 1 -2, G 1 -3, G 1 -4 or G 1 represents a structure represented by -5
  • G 2 Is G 2 -1, G 2 -2, G 2 -3, G 2 -4 or G 2 Represents a structure represented by -5
  • R 4 Is independently a hydrogen atom, a halogen atom, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 1 ⁇ C 6 Alkoxy, halo (C 1 ⁇ C 6 ) Alkoxy, halo (C 1 ⁇ C 6 ) Alkylthio, halo (C 1 ⁇ C 6 ) Alkylsulfinyl,
  • G 1 Is G 1 -1, G 1 -2, G 1 -3, G 1 -4 or G 1 Represents a structure represented by -5
  • G 2 Is G 2 -1, G 2 -2, G 2 -3, G 2 -4 or G 2 Represents a structure represented by -5
  • R 1 , R 2 , R 3 And R 4 Is independently a hydrogen atom, a halogen atom, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 1 ⁇ C 6 Alkoxy, halo (C 1 ⁇ C 6 ) Alkoxy, halo (C 1 ⁇ C 6 ) Alkylthio, halo (C 1 ⁇ C 6 ) Alkylsulfinyl or halo (C 1 ⁇ C 6 ) Represents alky
  • R A , R B , R C , R D And R E Is independently a hydrogen atom, a halogen atom, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 6 Cycloalkyl, substituted by U (C 3 ⁇ C 6 ) Cycloalkyl, C 1 ⁇ C 6 Alkoxy, halo (C 1 ⁇ C 6 ) Alkoxy, C 1 ⁇ C 6 Alkylthio, halo (C 1 ⁇ C 6 ) Alkylthio, C 1 ⁇ C 6 Alkylsulfinyl, halo (C 1 ⁇ C 6 ) Alkylsulfinyl, C 1 ⁇ C 6 Alkylsulfonyl, halo (C 1 ⁇ C 6 ) Alkylsulfonyl, —NY 3 Y 4 , Cyano, nitro or V V represents a structure represented by V-1, V-2,
  • D is a hydrogen atom, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 1 ⁇ C 6 Alkylcarbonyl, halo (C 1 ⁇ C 6 ) Alkylcarbonyl, C 1 ⁇ C 6 Alkylsulfonyl, halo (C 1 ⁇ C 6 ) Represents alkylsulfonyl
  • E is a hydrogen atom, C 1 ⁇ C 6 Alkyl, halo (C 1 ⁇ C 6 ) Alkyl, C 1 ⁇ C 6 Alkylcarbonyl, halo (C 1 ⁇ C 6 ) Alkylcarbonyl, C 1 ⁇ C 6 Alkylsulfonyl, halo (C 1 ⁇ C 6 ) Represents alkylsulfonyl.
  • Said at least one pesticidal compound or agent is Alanicarb, aldicarb, bendiocarb, benflacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiophenecarb, fenobcarb, formethanate, fratiothiocarb, isoprocarb, methiocarb, mesomil, oxamyl, pirimicarb, propoxur, thiodicarb, thiodicarb Knox, triazamate, trimetacarb, XMC, xylylcarb, metlcarb, phenothiocarb, phenoxycarb, acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyphos, kazusaphos, chlorethoxyphos, chlorfenpho
  • ⁇ 21> A method for controlling pests, comprising bringing the compound according to ⁇ 1> or a salt thereof or an N-oxide thereof into contact with the pest or its environment.
  • ⁇ 22> A method for increasing the vitality of a crop, comprising contacting the crop or the seed of the crop with the compound according to ⁇ 1>, a salt thereof, or an N-oxide thereof.
  • ⁇ 23> A seed treated with the compound according to ⁇ 1> or a salt thereof, or an N-oxide thereof, wherein the compound according to ⁇ 1> is present in an amount of about 0.0001 to about 50% by weight of the whole seed after the treatment. Or the seed comprising a salt thereof or an N-oxide thereof.
  • a method for producing seeds comprising a step of treating crop seeds with the compound according to ⁇ 1> or a salt thereof or an N-oxide thereof,
  • the seed after the treatment contains the compound according to ⁇ 1> or a salt thereof or an N-oxide thereof in an amount of about 0.0001 to about 50% by weight of the whole seed; The method.
  • the compounds encompassed by the present invention include optically active isomers resulting from the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms or axial asymmetry. Active or racemic forms are included.
  • the compounds included in the present invention may have tautomers depending on the type of the substituent, but the present invention relates to all tautomers or a mixture of tautomers containing the tautomers in any ratio. Is included.
  • the compounds included in the present invention may have geometric isomers due to imino groups, but the present invention includes all geometric isomers or a mixture of geometric isomers contained in any ratio. Things.
  • the geometric isomer resulting from the imino group includes, for example, a bond represented by a wavy line between D represented by the formula (1) and a nitrogen atom of the imino group. It is a mixture of isomers in any proportion.
  • those which can be converted into salts according to a conventional method include, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, salts of hydrohalic acids such as hydroiodic acid, Salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid; formic acid; Acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, carboxylic acid salts such as citric acid, glutamic acid, Salt
  • an N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocycle is oxidized.
  • the hetero ring capable of forming an N-oxide include a condensed ring containing a pyridine ring.
  • n- means normal
  • i- means iso
  • s- means secondary
  • tert- means tertiary
  • c- means cyclo
  • halogen atom in the present specification includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • halo in the present specification also represents these halogen atoms.
  • C a -C b alkyl in the present specification represents a straight-chain or branched-chain hydrocarbon group having ab carbon atoms, for example, a methyl group, an ethyl group, an n- Specific examples include propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, n-hexyl and the like. And are selected within the range of each specified number of carbon atoms.
  • halo (C a -C b ) alkyl in the present specification refers to a straight line composed of a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is replaced by an arbitrary number of halogen atoms. Represents a chain or branched hydrocarbon group, and when substituted by two or more halogen atoms, these halogen atoms may be the same or different from each other.
  • C a -C b cycloalkyl refers to a cyclic hydrocarbon group having ab carbon atoms and forms a monocyclic or composite ring structure of three to six members. Can be done. Further, each ring may be arbitrarily substituted with an alkyl group within the specified number of carbon atoms. Specific examples thereof include a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, a 2,2-dimethylcyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. It is selected in a range of numbers.
  • C a -C b alkoxy represents an alkyl-O- group having the above-mentioned meaning having from a to b carbon atoms, such as a methoxy group, an ethoxy group, an n-propyloxy group, an i- Specific examples include a propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and a 2-ethylhexyloxy group, each of which is selected within the range of the specified number of carbon atoms.
  • halo (C a -C b ) alkoxy represents a haloalkyl-O- group having the above-mentioned meaning having from a to b carbon atoms, such as a difluoromethoxy group, a trifluoromethoxy group and a chlorodifluoro group.
  • Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2-chloro-1 , 1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.
  • C a -C b alkylthio represents an alkyl-S— group having the above meaning having from a to b carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio. Specific examples include a group, an n-butylthio group, an i-butylthio group, an s-butylthio group, and a tert-butylthio group, which are selected within the range of the specified number of carbon atoms.
  • halo (C a -C b ) alkylthio in the present specification represents a haloalkyl-S- group having the above-mentioned meaning having from a to b carbon atoms, such as a difluoromethylthio group and a trifluoro group.
  • Methylthio chlorodifluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-tri Fluoroethylthio, pentafluoroethylthio, 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (tri Specific examples include a fluoromethyl) ethylthio group and a nonafluorobutylthio group, which are selected within the range of the specified number of carbon atoms.
  • C a -C b alkylsulfinyl represents an alkyl-S (O) — group having the above meaning having from a to b carbon atoms, and includes, for example, a methylsulfinyl group, an ethylsulfinyl group, an n- Specific examples thereof include a propylsulfinyl group, an i-propylsulfinyl group, an n-butylsulfinyl group, an i-butylsulfinyl group, an s-butylsulfinyl group, and a tert-butylsulfinyl group, and the range of each specified carbon atom number Is selected.
  • halo (C a -C b ) alkylsulfinyl in the present specification represents a haloalkyl-S (O)-group having the above-mentioned meaning having from a to b carbon atoms, for example, difluoromethyl Sulfinyl group, trifluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl ) Ethylsulfinyl group, nonafluorobutylsulfinyl group and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.
  • C a -C b alkylsulfonyl represents an alkyl-SO 2 — group having the above meaning having from a to b carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, and an n-propylsulfonyl.
  • halo (C a -C b ) alkylsulfonyl in the present specification means a haloalkyl-SO 2 — group having the above meaning having a to b carbon atoms, for example, a difluoromethylsulfonyl group , Trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1 , 1,2-trifluoroethylsulfonyl group and the like are mentioned as specific examples, and each is selected within the range of the specified number of carbon atoms.
  • C a -C b alkylcarbonyl represents an alkyl-C (O)-group having the above-mentioned meaning having from a to b carbon atoms, and includes, for example, an acetyl group, a propionyl group, a butyryl group, Specific examples include an isobutyryl group, a valeryl group, an isovaleryl group, a 2-methylbutanoyl group, a pivaloyl group, a hexanoyl group, a heptanoyl group, and the like are selected within the range of the specified number of carbon atoms.
  • halo (C a -C b ) alkylcarbonyl represents a haloalkyl-C (O)-group having the above-mentioned meaning having from a to b carbon atoms, and examples thereof include a fluoroacetyl group and a chloroacetyl group.
  • a noyl group or the like is mentioned as a specific example, and is selected within the range of each specified number of carbon atoms.
  • C a -C b alkoxycarbonyl represents an alkyl-OC (O)-group having the above meaning having from a to b carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, Specific examples include n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl. And selected within the range of each specified number of carbon atoms.
  • halo (C a -C b ) alkoxycarbonyl represents a haloalkyl-OC (O)-group having the above-mentioned meaning having from a to b carbon atoms, for example, chloromethoxycarbonyl group , 2-chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2, -trifluoroethoxycarbonyl group, 2,2,2, -trichloroethoxycarbonyl group, and the like. Is selected within the range of the specified number of carbon atoms.
  • (C a -C b ) cycloalkyl substituted by U refers to the above-mentioned having from a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is replaced by an arbitrary number of U atoms. Represents a cycloalkyl group that is meant to be selected within the range of each specified number of carbon atoms. At this time, when there are two or more substituents U on each (C a -C b ) cycloalkyl group, each U may be the same or different.
  • G 1 is G 1 -1, R 1, R 2, R 3 and R 4, Each independently represents a hydrogen atom, a halogen atom, halo (C 1 -C 6 ) alkyl, halo (C 1 -C 6 ) alkylthio, halo (C 1 -C 6 ) alkylsulfinyl, halo (C 1 -C 6 ) Alkylsulfonyl, RA is C 1 -C 3 alkoxy, halo (C 1 -C 3 ) alkoxy, C 1 -C 3 alkylthio, halo (C 1 -C 3 ) alkylthio, C 1 -C 3 alkylsulfonyl , Halo (C 1 -C 3 ) alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol
  • G 1 is G 1 -1, R 1, R 2, R 3 and R 4 A hydrogen atom, halo (C 1 -C 3 ) alkyl
  • RA is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, and A 1 Is C—R C
  • a 2 is N
  • R B and R D are hydrogen atoms
  • R C is each independently phenyl optionally substituted with up to two Z
  • Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy
  • D is a hydrogen atom, acetyl
  • E is a hydrogen atom, C 1 ⁇ C 3 alkyl Cyclopropylmethyl, halo (C 1 -C 3 ) alkyl
  • RA is ethylthio
  • G 1 is G 1 -1, R 1, R 2, R 3 and R 4 A hydrogen atom, halo (C 1 -C 3 ) alkyl
  • RA is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl
  • a 2 is C-R E
  • a 1 is N
  • R C is may be substituted by each independently up to two Z-phenyl, 1H -Pyrazol-1-yl, 2H-1,2,3-triazol-2-yl
  • Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy
  • D is a hydrogen atom
  • E is a hydrogen atom, C 1 ⁇ C 3 alkyl Cyclopropylmethyl, halo (C 1 -C 3 ) alkyl
  • RA is ethylthi
  • RA is more preferably ethylthio or ethylsulfonyl.
  • a salt thereof or an N-oxide thereof particularly preferably, 3- (ethylsulfonyl) -5- (1H-pyrazol-1-yl) -N- (5- (trifluoromethyl) pyridin-2-yl) picolinimidamide (Compound No. 91); 3- (ethylsulfonyl) -5- (1H-pyrazol-1-yl) -N- (4- (trifluoromethyl) pyridin-2-yl) picolinimidamide (Compound No.
  • G 2 is G 2 -1
  • R 1 , R 2 , R 3 and R 4 are Each independently represents a hydrogen atom, a halogen atom, halo (C 1 -C 6 ) alkyl, halo (C 1 -C 6 ) alkylthio, halo (C 1 -C 6 ) alkylsulfinyl, halo (C 1 -C 6 ) Alkylsulfonyl
  • R A is C 1 -C 3 alkoxy, halo (C 1 -C 3 ) alkoxy, C 1 -C 3 alkylthio, halo (C 1 -C 3 ) alkylthio, C 1 -C 3 alkylsulfonyl , Halo (C 1 -C 3 ) alkylsulfonyl, 1H-pyrazol-1-yl,
  • G 2 is G 2 -1 and R 1 , R 2 , R 3 and R 4 are A hydrogen atom, halo (C 1 -C 3 ) alkyl, RA is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, and A 1 Is C—R C ;
  • a 2 is N;
  • R B and R D are hydrogen atoms;
  • R C is each independently phenyl optionally substituted by up to two Z; -Pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, dimethylamino, and Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.
  • RA is more preferably ethylthio or ethylsulfonyl.
  • a salt thereof or an N-oxide thereof particularly preferably, 2- (3- (1H-pyrazol-1-yl) pyridin-4-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine (Compound No. 46) , 2- (3- (2H-1,2,3-triazolo-2-yl) pyridin-4-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyridine (Compound No.
  • a salt thereof or an N-oxide thereof most preferably, 2- (3- (ethylsulfonyl) -5- (2- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] pyridine (Compound No. 174), 2- (3- (ethylsulfonyl) -5- (3- (trifluoromethyl) phenyl) pyridin-2-yl) -6- (trifluoromethyl)-[1,2,4] triazolo [1,5- a] pyridine (Compound No.
  • G 2 is G 2 -1 and R 1 , R 2 , R 3 and R 4 are Each independently represents a hydrogen atom, a halogen atom, halo (C 1 -C 6 ) alkyl, halo (C 1 -C 6 ) alkylthio, halo (C 1 -C 6 ) alkylsulfinyl, halo (C 1 -C 6 ) Alkylsulfonyl, R A is C 1 -C 3 alkoxy, halo (C 1 -C 3 ) alkoxy, C 1 -C 3 alkylthio, halo (C 1 -C 3 ) alkylthio, C 1 -C 3 alkylsulfonyl , Halo (C 1 -C 3 ) alkylsulfonyl, 1H-pyrazol-1-yl, 2
  • G 2 is G 2 -1 and R 1 , R 2 , R 3 and R 4 are A hydrogen atom, halo (C 1 -C 3 ) alkyl, R A is C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfonyl, A 1 is C—R C , and A 2 is , N, R B and R D are hydrogen atoms, and R C is each independently phenyl optionally substituted with up to two Z, 1H-pyrazol-1-yl, 2H-1,2H. , 3-triazol-2-yl, and Z is hydrogen, fluorine, chlorine, trifluoromethyl, or trifluoromethoxy.
  • G 2 is G 2 -1 and R 1 , R 2 , R 3 and R 4 are A hydrogen atom, halo (C 1 -C 3 ) alkyl, R A is C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfonyl, A 2 is C—R E , and A 1 is , N, R B and R D are hydrogen atoms, and R C is each independently phenyl optionally substituted with up to two Z, 1H-pyrazol-1-yl, 2H-1,2H. , 3-triazol-2-yl, and Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.
  • RA is more preferably ethylthio or ethylsulfonyl.
  • a salt thereof or an N-oxide thereof more preferably, 2- (3- (ethylsulfonyl) -5- (1H-pyrazol-1-yl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2-a] [1,3 , 5] Triazin-4-one (Compound No. 193) 2- (3- (ethylsulfonyl) -5- (2H-1,2,3-triazol-2-yl) pyridin-2-yl) -7- (trifluoromethyl) -4H-pyrido [1,2- a] [1,3,5] triazin-4-one (Compound No.
  • the compound represented by the formula (1), (2) or (3) or a salt thereof or an N-oxide thereof (hereinafter, also referred to as the compound of the present invention) of the present invention can be produced, for example, by the following production method.
  • the present invention is not limited to these.
  • Step a The amidine compound represented by the formula (1-1) is reacted with an amine compound represented by the formula (4) and a cyano compound represented by the formula (5) in the presence of a base and an inert solvent. Can be manufactured. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79 (10), p. 4687-4693).
  • Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride, normal butyl lithium, sodium bis (trimethylsilyl) amide, and lithium bis (trimethylsilyl) amide. , Potassium bis (trimethylsilyl) amide, lithium diisopropylamine, and the like, but the reactants that can be used in this reaction are not limited thereto.
  • the amount of the base to be used is generally about 1- to 3-fold the molar quantity of the compound represented by the formula (4).
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction.
  • examples thereof include linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; and aromatic hydrocarbons such as benzene, toluene, and xylene. Hydrogens; polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone; and the like. A mixture of more than one species can be used.
  • the reaction temperature in this reaction may be generally in the range of ⁇ 78 ° C. to the boiling point of the solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours.
  • the cyano compound represented by the formula (5) is usually used in a range of about 1/3 mole to 1 mole or about 1 mole to 3 moles of the amino compound represented by the formula (4).
  • This reaction can also be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purifying by recrystallization, column chromatography or the like as necessary.
  • Lewis acids that can be used in the present reaction include trimethylaluminum, aluminum chloride, titanium tetrachloride and the like, but the reactants that can be used in the present reaction are not limited thereto.
  • the amount of the Lewis acid to be used is generally about 1- to 3-fold the molar amount of the compound represented by the formula (4).
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene; and halogenated solvents such as dichloromethane and 1,2-dichloroethane. These inert solvents can be used alone or in combination of two or more.
  • the reaction temperature in this reaction may be usually in the range of 0 ° C. to the boiling point of the solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours.
  • the cyano compound represented by the formula (5) is generally used in a range of about 1 to 3 moles relative to the amino compound represented by the formula (4).
  • This reaction can also be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Step b When D is not a hydrogen atom, the amidine compound represented by the formula (1-1) is reacted with a reactant in the presence of a base and an inert solvent as the case may be, and thereby represented by the formula (1-2). Amidine compounds can be produced.
  • R A , R B , R D , A 1 , A 2 , G 1 and D indicate the same as above.
  • Examples of the reactants that can be used in the present invention include acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, acid chlorides such as methanesulfonic acid chloride, trifluoromethanesulfonic acid chloride, acetic anhydride, trifluoroacetic anhydride, Acid anhydrides such as trifluorosulfonic anhydride; alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, dimethyl sulfate, etc., which can be used in this reaction.
  • the reactant is not limited to this.
  • the amount of the reactant to be used may be appropriately selected usually in the range of about 1 to 3 mol per mol of the compound represented by the formula (1-1), and the reactant such as acetic anhydride is added in excess.
  • the reaction can be performed without a solvent.
  • Examples of the base that can be used in the present invention include alkali metal hydrides such as triethylamine, N, N-diisopropylethylamine, pyridine, lithium hydride, sodium hydride, potassium hydride, calcium hydride, normal butyl lithium, sodium bis (Trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, lithium diisopropylamine and the like can be used, and the amount of use is usually about 1-fold that of the compound represented by the formula (8). It may be appropriately selected within the range of from mol to 5 times mol.
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction.
  • examples thereof include linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; and aromatic hydrocarbons such as benzene, toluene, and xylene.
  • examples include polar solvents such as hydrogens, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, and the like. A mixture of more than one species can be used.
  • the reaction temperature in this reaction may be generally in the range of about ⁇ 78 ° C. to the boiling point of the solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. good.
  • This reaction can also be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Step c When E is not a hydrogen atom, the amidine compound represented by the formula (1) is produced by reacting the amidine compound represented by the formula (1-2) with a reactant in the presence of a base and an inert solvent. can do.
  • R A , R B , R D , A 1 , A 2 , G 1 , D and E indicate the same as above.
  • Examples of the reactants that can be used in the present invention include acid chlorides such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonic acid chloride, trifluoromethanesulfonic acid chloride; acetic anhydride, trifluoroacetic anhydride, Acid anhydrides such as trifluorosulfonic anhydride; and alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, and dimethyl sulfate.
  • the agent is not limited to this.
  • the amount of the reactant to be used may be appropriately selected usually in the range of about 1 to 3 moles per mole of the compound represented by the formula (1-2).
  • Examples of the base that can be used in the present invention include alkali metal hydrides such as triethylamine, N, N-diisopropylethylamine, pyridine, lithium hydride, sodium hydride, potassium hydride, calcium hydride, normal butyl lithium, sodium bis (Trimethylsilyl) amide, lithium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, lithium diisopropylamine, and the like can be used.
  • the amount of the compound is generally about the amount of the compound represented by the formula (1-2). It may be appropriately selected within the range of 1 to 5 moles.
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; and aromatic hydrocarbons such as benzene, toluene, and xylene.
  • linear or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane
  • aromatic hydrocarbons such as benzene, toluene, and xylene.
  • Examples include polar solvents such as hydrogens, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, and the like.
  • a mixture of more than one species can be used.
  • the reaction temperature in this reaction may be generally in the range of about ⁇ 78 ° C. to the boiling point of the solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. good.
  • This reaction can also be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • An amidine compound represented by the formula (2) can be produced by reacting an amidine compound represented by the formula (1-1) with a reactant in the presence of an inert solvent. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79 (10), p. 4687-4693).
  • R A , R B , R D , A 1 , A 2 , G 1 and G 2 are the same as above.
  • Examples of the reactant usable in the present invention include iodobenzene diacetate, (bis (trifluoroacetoxy) iodo) benzene, iodosylbenzene, (hydroxy (tosyloxy) iodo) benzene, 2-iodoxybenzoic acid, and Dess-Martin.
  • An oxidizing agent such as a hyperatomized iodine compound such as periodinane is exemplified, but the reactant that can be used in this reaction is not limited thereto.
  • the amount of the reactant to be used may be appropriately selected usually in the range of about 1 to 5 mol per mol of the compound represented by the formula (1-1).
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include halogenated solvents such as dichloromethane and 1,2-dichloroethane, and aromatic hydrocarbons such as benzene, toluene, and xylene. , Methanol, ethanol, propanol, 2,2,2-, trifluoroethanol, hexafluoro-2-propanol and the like, and ethyl acetate, acetonitrile and the like. A mixture of more than one species can be used.
  • halogenated solvents such as dichloromethane and 1,2-dichloroethane
  • aromatic hydrocarbons such as benzene, toluene, and xylene.
  • the reaction temperature in this reaction may be generally in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .
  • This reaction can also be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Step e The amidine compound represented by the formula (3) can be produced by reacting the amidine compound represented by the formula (1-1) with a reactant in the presence of a base and an inert solvent.
  • R A , R B , R D , A 1 , A 2 , G 1 and G 2 are the same as above.
  • Examples of the reactants that can be used in the present invention include methyl chlorocarbonate, ethyl chlorocarbonate, phenyl chloroformate, 4-nitrophenyl chloroformate, 4-chlorophenyl chloroformate, phosgene, triphosgene, carbonyldiimidazole, and the like.
  • the reactants that can be used in this reaction are not limited to this.
  • the amount of the reactant to be used may be appropriately selected usually in the range of about 1 to 5 mol per mol of the compound represented by the formula (1-1).
  • Examples of the base that can be used in the present invention include triethylamine, N, N-diisopropylethylamine, pyridine and the like, and the amount of the base is usually about 1 to the compound represented by the formula (1-1). It may be appropriately selected in the range of 2 to 5 times mol.
  • the inert solvent that can be used in this reaction may be any solvent that does not significantly inhibit this reaction, and examples thereof include halogenated solvents such as dichloromethane and 1,2-dichloroethane, and aromatic hydrocarbons such as benzene, toluene, and xylene.
  • halogenated solvents such as dichloromethane and 1,2-dichloroethane
  • aromatic hydrocarbons such as benzene, toluene, and xylene.
  • Chain or cyclic ethers such as benzene, diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene and xylene, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, 1,3- Examples thereof include polar solvents such as dimethyl-2-imidazolinone, ethyl acetate, and acetonitrile. These inert solvents can be used alone or as a mixture of two or more.
  • the reaction temperature in this reaction may be generally in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not fixed depending on the reaction scale, the reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. .
  • This reaction can also be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Pests to be Controlled are not particularly limited, and can be used for control of pests, mites, nematodes, and soil pests in a wide range of agricultural and horticultural products, including insecticides. In the present invention, these pests are defined as agricultural and horticultural pests.
  • Preferred insect species to be controlled include, for example, the following.
  • Lepidoptera for example, Chilo suppressalis; Darkheaded stem borer (Chilo polychrysus); White stem borer (Scirpophaga innotata); , Riceha casino potato (Marasmia exigua), Watanomeiga (Notarcha derogata), Awanomeiga (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Himadara nomeiga (Hellula undalis), Monkikuro nomeiga (Herpetale tera stu) ); Rice worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc .; (Crambidae); litura) White armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm (Mamestra brassicae), rice armyworm (Sesamia inferens), armyworm (Spodoptera mauritia), Naruga
  • Pseudoconspersa such as Pseudoconspersa; Pluteliidae such as Plutella xylostella; Pluteliidae; ), Potato moths (Phthorimaea operculella), Tuta absoluta, etc .; (Gelechiidae); Cossida (Cossida) such as Cossus insularis e); Geometridae, such as Ascotis selenaria; Limacodidae, such as Parahelia lepida; Lachesis, etc .; Sphingidae; Nokona feralis, etc .; and Sespidae, such as Parnara guttata.
  • Hemiptera pests for example, the brown planthopper (Laodelphax striatellus), the brown planthopper (Nilaparvata lugens), the brown planthopper (Sogatella furcifera), the corn planthopper (Peregrinus maidicida), the yellow-tailed planthopper (Javesella pellicida pellucida, pellicida pellicida) Orizicolus and other planthoppers (Delphacidae); black leafhoppers (Nephotettix cincticeps); Leafhoppers (Cicadellidae) such as Empoasca fabae, corn leaf hopper (Dalbulus maidis), and white leafhopper (Cofana spectra); Cercopidae (Cercopidae) such as Mahanarva posticata and Mahanarva fimbriolata; Mephia aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton
  • Coleoptera (Coleoptera)-For example, Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), banded canker Beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), beetle beetle (Oulema melanopus), beetle beetle (Aulacophora femoralis), and beetle flea beetle (Phyllotreta beta freta striola fleet) , Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), leaf beetle (Lept
  • Thysanoptera pests for example, Citrus thrips (Frankliniella occidentalis), Thrips palmi (Thrips palmi), Thrips palmi (Thomas), Thrips tabaci Thripidae (Thripidae) such as Stenchaetothrips biformis and E. thrips (Echinothrips americanus); and Thripidae (Phlaeothripidae) ⁇ such as rice thrips (Haplothrips aculeatus).
  • Diptera For example, anthromycidae (Anthomyiidae), such as pupae (Delia platura) and onion fly (Delia antiqua); ), Tomato leaf flies (Liriomyza sativae), bean leaf flies (Liriomyza trifolii), spider flies (Chromotomyia horticola), etc.
  • anthromycidae such as pupae (Delia platura) and onion fly (Delia antiqua);
  • Tomato leaf flies Liriomyza sativae
  • bean leaf flies Liriomyza trifolii
  • spider flies Chomotomyia horticola
  • Hymenoptera for example, Tenthredinidae (e.g., Afalia rosae, Athalia japonica); Fire Ant (Solenopsis spp.); Brown leaf-cutting ant (Atta capiguara) Ants (Formicidae) and so on.
  • Tenthredinidae e.g., Afalia rosae, Athalia japonica
  • Fire Ant Solenopsis spp.
  • Brown leaf-cutting ant Anttta capiguara
  • Orthoptera pests eg, Locusta migratoria
  • Morocco locusts Dociostaurus maroccanus
  • Australian locusts Chortoicetes terminifera
  • Red locusts Nomadacris septemfasciata
  • Brown Locust Locustana parlana na, Locustana pardalina
  • Italian Locust Calliptamus italicus
  • Differential grasshopper (Melanoplus differentialis)
  • Two striped grasshopper (Melanoplus bivittatus)
  • Migratory grasshopper Migratory grasshopper (Melanoplus sanguinipes
  • Red-Legged grasshopper Molanoplus femurrubrum
  • Clearwinged grasshopper (Camnula grasshopper) (Schistocerca gregaria); Yellow-winged locust (Gastrimargus musicus); Spur-throated locust (Austracris guttulosa); Gryllotalpa oriental
  • Cockroach pests (Blattodea)-For example, German cockroaches (Blattella germanica) and other German cockroaches (Blattellidae); Cockroaches (Blattidae) such as the cockroach (Periplaneta japonica) and the cockroach (Periplaneta australasiae); Termites (Odontotermes formosanus), Koshun termites (Neotermes koshunensis), Satsuma termites (Glyptotermes satsumensis), Naka termites (Glyptotermes nakajimai), Catan termites (Glyptotermes fuscus), The termites (Hodotermopsis sjostedti), the termites (Coptotermes guangzhouensis), the amami termites (Reticulitermes amamianus), the termites (Reticulitermes miyatakei), the termites (Reticulitermes kanmonene
  • Acari pests eg, Tetranychus urticae
  • Tetranychus kanzawai Tetranychus evansi
  • Tetranychus evansi Tetranychus evansi
  • Panonychus citri Panonychus ulmi, Olonycus sp.
  • Tripalpidae such as Brevipalpus phoenicis
  • Tuckerellidae Polygonidae
  • Haemaphysalis longicornis Haemaphysalis flava
  • Ixodidae such as Ixodes persulcatus, Ixodes persulcatus, Ixodes scapularis, Amblyomma americanum, Boophilus microplus, and Rhipicephalus sanguineus.
  • Acaridae such as Tyrophagus putrescentiae and Tyrophagus similis
  • Dermatophagidae such as Dermatophagoides farinae and Dermatophagoides pteronyssinus, such as Dermatophagoides farinae and Dermatophagoides pteronyssinus
  • Dermatophagoides farinae and Dermatophagoides pteronyssinus Species of the family Dermatophagoides (Cheyletidae), Otodectes cynotis (Otodectes cynotisarc, etc.), such as the red mite (Cheyletus eruditus), the stag beetle (Cheyletus malaccensis), the southern red mite (Cheyletus moorei), and the dog mite (Cheyletiella yasguri).
  • Demodicidae such as Demodex canis (Demodex canis); Listrophoridae; (Dermanyssidae) such as (Dermanyssus gallinae); and the like (Trombiculidae) such as Leptorombidium akamushi.
  • Plant parasitic nematodes for example, Ahelenida, Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, Bursaphelenchus xylophilus such as Bursaphelenchus xylophilus
  • Potato white cyst nematode (Globodera pallida), potato cyst nematode (Globodera rostochiensis), wheat cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera schachtii), folia oli (Heterodera schachtii)
  • Rear root knot nematode (Meloidogyne arenaria), northern root root nematode (Meloidogyne hapla), sweet potato root nematode (M
  • the compounds of the present invention can further be used for controlling pests such as sanitary pests, storage pests, clothing pests, house pests and parasites. In particular, they are also excellent in controlling harmful invertebrates that harm humans and animals, and these pests are defined as animal parasitic pests in the present invention.
  • Animal parasitic pests to be controlled include those that infest the host animal's back, armpits, lower abdomen, and inner thighs and obtain nutrients such as blood and dandruff from animals and birds, and Includes animals that fly to the back, buttocks, etc. of animals and obtain nutrients such as blood and dandruff from animals and birds.
  • Animal parasitic pests include mites, lice, fleas and the like.
  • Examples of host animals for which the control agent of the present invention is effective include humans, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, and ferrets; Canary); cattle, horses, pigs, sheep, goats; poultry (eg, ducks, chickens, quails, geese); honey bees (eg, honey bees, Japanese honey bees);
  • the pesticidal composition of the present invention is effective as an animal parasitic pest controlling composition for protecting the above-mentioned animals and birds.
  • Mites of the order Mesostigmata eg, Dermanyssus gallinae
  • Dermanyssidae or Dermanyssidae
  • Ornithonyssus spp . Ornithonyssus sylviarum
  • Ornithonyssus bur And mites of the family Dermatophagoides (Macronyssidae), including the house dust mite (Ornithonyssus bacoti);
  • Mites of the family Acaridae (Varroidae), including the spider mite spp.
  • Hatophylla Haemaphysalis otophila
  • Haemaphysalis leachi Haemaphysalis longicornis
  • Haemaphysalis mageshimaensis Haemaphysalis yeni
  • Haemaphysalis yeni Haemaphysalis yeni
  • Haemaphysalis yeni Haemaphysalis pentalagi
  • Haemaphysalis flava Haemaphysalis megaspinosa
  • Haemaphysalis japonica Haemaphysalis japonica
  • Haemaphysalis douglasi Amblyomma sp.
  • Rhipicephalus evertsi Rhipicephalus sanguineus, Rhipicephalus bursa, Ripicephalus appendiculatus, Rhipicephalus appendiculatus, lupus phas (Rhipicephalus turanicus), Rhipicephalus zambeziensis, Dermacentor sp. (Dermacentor marginatus), Dermacentor reticulata (Dermacentor reticulatus), Dermacentor reticulatus (Dermacentor reticulatus) ), Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis (Dermacentor albipictus) Ixodidae mites including centor variabilis.
  • Louse family (Haematopinus spp.) Including, for example, louse lice (Haematopinus spp.), Sea lice (Haematopinus asini), bovine lice (Haematopinus eurysternus), and lice (Haematopinus suis); Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformisn, Linognathus nosgisnos, Linognathus oginasisino, and Linognathus oginasisinos, Linognathus oginasisinos, Linognathus oginasisinos, Linognathus oginasisinos, Linognathus ogisunas, Linognathus ogisunas, Linognathus ogisunas, Linognathus ogisunas, Linogna
  • Biting louses of the order Amblycera such as Menacanthus spamine.
  • a louse lice of Menoponidae (Menoponidae) including a chick whitefly (Menopon gallinae) of the genus Menopon spp.
  • Biting louse of Ischnocera for example, Columbicola spp.), Columbicola columbae, and Cuclotogaster spp.
  • a flea of the family Sinidae including a snow flea (Tunga penetrans) of the genus Tunga spp .
  • a flea canis) of a flea species (Ctenocephalides spp.
  • a flea (Ctenocephalides felis); Hedgehog flea (Archaeopsylla erinacei) of Archaeopsylla spp., Oriental flea (Xenopsylla cheopis) of a flea species (Xenopsylla spp.), Human flea (Pulex irritans) of a flea species of Pulex spp.
  • Fleas of the family Flea (Pulicidae) including elder fleas (Echidnophaga gallinacea); Flea of the family Ceratophyllidae, including the European flea (Nosopsyllus fasciatus); Fleas of the family Lepidoptera (Leptopsyllidae), including the white flea (Leptopsylla segnis) of the species Lepidoptera (Leptopsylla spp.).
  • Other animal parasitic pests of interest include pests of the order Hemiptera. The following pests are mentioned as pests of the order Hemiptera.
  • insects of the family Bed Bug including Bed Bugs (Cimex lectularius) of the genus Spimex (Cimex spp.); Panstrongylus spp .; and Rhododnius spp.
  • Rhodnius species Rhodnius spp.
  • prolixus insects of the family Reduviidae
  • Reduviidae insects of the family Reduviidae
  • Triatoma infestans Triatoma infestans
  • Diptera pests which are biting insects (chewing flies, blood-sucking flies, migratory dipterous larvae, and parasitoid flies).
  • the following insect pests can be mentioned as flies (Diptera).
  • Nematocera eg, (a) Culex spp.) Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Armigeres spp.
  • Tabanus spp. Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus
  • Tabby Tabanus trigonus
  • red-tailed tabby Tabanus chrysurus
  • red-winged pigeon Tabanus trigeminus
  • cypress tabby Tabanus fulvimedioides
  • red-billed lobster Tabanus iyoensis
  • Chrysops sp. ⁇ Flies of Tabanidae including Chrysops relictus, Chrysops suavis and Chrysops japonicus; Houseflies of Musca spp .
  • Musca domestica Musca bezzi (Musca hervei), the house fly Musca conducens)
  • Musca stabulans Stomoxys spp.
  • Flies (Stomoxys calcitrans), Haematobia spp. Flies of the family Muscidae, including Haematobia stimulans, Haematobia stimulans and Fannia canisularis of the genus Musca domestica (Fannia spp.); And Glossinidae (Glossinidae) including the genus Glossina spp. Flies; Melopagas spp .; lice flies including the louse fly (Melophagus ovinus); Hipfoboscidae; flies; Calliphora; large fly (Calliphora lata); kinfly sp.
  • Hypodermatinae and also of the genus Species (Hypoderma spp.) Of the genus Species (Hypoderma spvis), Hypoderma bovis, Hypoderma lineatum, and of the subfamily Gasterophilinae (Gasterophilus spp.). Horsefly (Gasterophilus intestinalis); And Oestridae flies including Oestrus ovis (Oestrus spp.).
  • the compound of the present invention When the compound of the present invention is used as a pesticide for agricultural and horticultural use, the compound of the present invention may be used as it is. Suitable solid carriers, liquid carriers, gaseous carriers, etc., surfactants, dispersants, and other preparations A pesticide formulation may be used by mixing with an auxiliary for use.
  • As the pesticide preparation preferably, emulsion, EW, liquid, suspension, wettable powder, wettable powder, powder, DL powder, powder, granule, granule, tablet, oil, aerosol, flowable, dry Flowables, microcapsules and the like can be mentioned. These pesticide preparations can be used as arbitrarily selected dosage forms.
  • the carrier in the present invention refers to a solid carrier, a liquid carrier, a gaseous carrier and the like.
  • the solid carrier examples include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, quartz sand, quartzite, zeolite, pearlite, attapulgite, pumice, ammonium sulfate, sodium sulfate, urea and the like.
  • the liquid carrier examples include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol and propylene glycol; ketones such as acetone, methyl ethyl ketone and cyclohexanone; and aliphatic hydrocarbons such as n-hexane, kerosene and kerosene.
  • Aromatic hydrocarbons such as toluene, xylene and methylnaphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamide, dimethylacetamide and the like Acid amides, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, water and the like.
  • the gaseous carrier include LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like.
  • Examples of the surfactant and the dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonate, and alkyl sulfosuccinic acid. Salt, formalin condensate of alkyl naphthalene sulfonate, polycarboxylate, POE polystyryl phenyl ether sulfate and phosphate, POE / POP block polymer and the like.
  • formulation auxiliary for example, carboxymethylcellulose, hydroxypropylcellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer,
  • formulation auxiliaries can be used alone or in combination as necessary.
  • the content of the compound of the present invention, which is an active ingredient, in the pesticide formulation is not particularly limited, but is preferably 1 to 75% by weight for emulsion, 0.3 to 25% by weight for powder, and 1 to 25% for wettable powder. 90% by weight, and 0.1 to 10% by weight for granules.
  • the amount used is not particularly limited.
  • the active ingredient can be used in an amount of 0.01 to 1000 mg.
  • the compounds of the present invention can be applied to host animals by known veterinary techniques. For example, when the purpose is systemic suppression, for example, a method of administering to animals by tablets, capsules, immersion liquid, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.).
  • methods such as spraying, pouring (pour-on), or dropping (spot-on) an oily or aqueous solution, and kneading the compound into a resin
  • methods such as spraying, pouring (pour-on), or dropping (spot-on) an oily or aqueous solution, and kneading the compound into a resin
  • the kneaded material is formed into an appropriate shape such as a collar, ear tag, or the like, and the obtained material is attached to an animal.
  • the pesticidal agent according to the present invention can be used as it is or diluted.
  • the pesticidal composition according to the present invention can be mixed with or used in combination with other insecticides, nematicides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, and the like.
  • drugs that can be mixed or used in combination include, for example, the Pesticide Manual (17th edition, published by The British Crop Protection Council) and the Shibuya Index (SHIBUYA INDEX 17th Edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP) and Eye Rack mode of action classification scheme (Mode of Action Classification Scheme Version 8.2 version, issued by IRAC), Eflac code list (FRAC Code List (c) * 2017: Fungicides sorted by mode of action, 2017 version, FRAC) and those whose structure can be specified on the Internet (http://www.alanwood.net/pesticides/sitemap.html).
  • the insecticide for example, alanicarb (alanycarb), aldicarb (aldicarb), bendiocarb (bendiocarb), benfuracarb (benfuracarb), butocarboxime (butocarboxim), butoxycarboxim (butoxycarboxim), carbaryl ( (carbaryl), carbofuran (carbofuran), carbosulfan (carbosulfan), ethiophencarb (ethiofencarb), fenobucarb (formonate), formethanate (formetanate), furathiocarb (furathiocarb), isoprocarb (isoprocarb), methiocarb (methiocarb), mesomemil (methomyl) Oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur), thiodicarb (thiodicarb), thiophanox (thiofanox),
  • nicotine nicotine (nicotine), chloropicrin (chloropicrin), sulfuryl fluoride (sulfuryl fluoride), crylotie (crylotie), clofentezine (clofentezine), diflobidazine (diflovidazin), rotenone (rotenone), India Xacarb (indoxacarb), piperonyl butoxide, piperonyl butoxide, chlordimeform, pyridalyl, pyridalyl, azadirachtin, benzoxymate, benzoxymate, afidopyropen, afludopyropen, fluhexafon, fluhexafon, fluhexafon, fluhexafon Benclothiaz (benclothiaz), carzole (carzole), insecticidal soap, dimehypo, nithiazine (nithiazine), borate
  • Fungicides used are, for example, metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), oxadixyl (oxadixyl), offose (ofurase), benalaxyl (benalaxyl), benalaxyl-M (benalaxyl-M), kiraraxyl (kiralaxyl) , Ofurace (ofurace), furalaxyl (furalaxyl), cyprofuran (cyprofuram) phenylamide compounds Hydroxypyrimidine-based compounds such as buprimate (bupyrimate), dimethylimol (dimethilimol), etirimol (ethilimol), Hymexazole (hymexazole), isoxazole compounds such as hydroxyisoxazole (hydroxyisoxazole), Piperidinyl thiazole isoxazoline compound such
  • quinofumelin quinofumelin
  • dipymetitron dipymetitrone
  • picarbutrazox picarbutrazox
  • technazen tecnazen
  • nitrtar-isopropyl nitrthal-isopropyl
  • dicyclomet dicyclomet
  • acibenzolar acibenzolar
  • Prohexadione-calcium prohexadione-calcium
  • bronopol bronopol
  • diphenylamine diphenylamine
  • flumetover flumetover
  • bentoxazine bethoxazin
  • biphenyl biphenyl
  • broloroneb chloroneb
  • CNA iodocarb
  • prothiocarb prothiocarb
  • the compound of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof can be used for controlling a target pest by applying an effective amount thereof to a plant or soil.
  • the amount of the active ingredient in the preparation is from 0.01 to 90% by weight.
  • Water-dispersible powders, emulsions, suspensions, flowables, aqueous solvents, and water-dispersible granules are diluted with water to the desired concentration, and then dissolved, suspended or emulsified into powders and granules. Can be sprayed on plants or soil as it is.
  • the emulsion, wettable powder, flowable and the like may be diluted with water to a desired concentration before application. Oils, aerosols, aerosols, poison baits, mite-proof sheets, etc. can be used as they are.
  • the term "crop" refers to cultivated plants in general, and specifically refers to food crops, feed crops, green manure crops, horticultural crops (including ornamental plants), and craft crops.
  • the invention also includes a method of increasing the vitality of a crop, the method comprising the step of contacting the crop or crop seed with a compound of the invention.
  • the present invention also includes a method of producing crop seed, the method comprising the step of treating the crop seed with a compound of the present invention.
  • the amount of the compound of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof is not limited. It is preferred to include a compound of the present invention or an agriculturally and horticulturally acceptable acid addition salt thereof in an amount of about 50% by weight.
  • the present invention further provides the use of a compound of the present invention or an acid addition salt thereof as an active ingredient of a composition for protecting animals and birds from animal parasitic pests.
  • the composition comprises the compound of the present invention or an acid addition salt thereof in an amount that is parasiticidally effective and does not harm the target animal or bird.
  • the compound of the present invention or an acid addition salt thereof is brought into contact with a pest or a growth environment thereof, such as an animal / bird, a crop, a crop seed, or soil, in a biologically effective amount to control pest invertebrates. I do.
  • G 1 of the formula (1) is G 1 -1 in the formula (1-3), R 1, R 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 1, D is a substituent described in Table 2, E is a substituent described in Table 3, R a is a substituent described in Table 4, R B, R D, is R E in Table 5
  • the compound of the present invention which is a combination of the above substituents.
  • G 1 of the formula (1) is G 1 -1 in the formula (1-3), R 1, R 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 6, D is a substituent described in Table 2, E is a substituent described in Table 3, R a is a substituent described in Table 4, R B, R C, R D is described in Table 7 A compound of the present invention which is a substituent of
  • G 2 of formula (2) is G 2 -1
  • R 1, R 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 1
  • R a is a substituent described in Table 4
  • R B, R D, R E is a compound of the invention or a substituted group described in Table 5.
  • G 2 of formula (2) is G 2 -1
  • R 1, R 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 6,
  • RA is a substituent shown in Table 4
  • R B , R C , and RD are substituents shown in Table 7.
  • G 2 is G 2 -1 of the formula (3), R 1, R 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 1, R a is a substituent described in Table 4, R B, R D, R E is a compound of the invention or a substituted group described in Table 5.
  • G 2 is G 2 -1 of the formula (3), R 1, R 2, R 3, R 4, A 1, A 2 is a substituted group described in Table 6, A compound of the present invention in which RA is a substituent shown in Table 4 and R B , R C , and RD are substituents shown in Table 7.
  • the obtained organic layer was dried over anhydrous magnesium sulfate and filtered.
  • the solvent was distilled off under reduced pressure using an evaporator.
  • the obtained crude product was purified by silica gel chromatography to obtain the desired product (8.8 mg, 6.5%, yellow viscous substance).
  • methyl iodide (30 ⁇ L, 0.40 mmol) was added, and the mixture was stirred at the same temperature for 30 minutes. Further, sodium hydride (content: 55%, 22 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. Then, methyl iodide (30 ⁇ L, 0.40 mmol) was added, and the mixture was stirred at the same temperature for 2.5 hours. Water was added, and the mixture was extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure using an evaporator.
  • Synthesis Example 2-1-10 Preparation of 5- (dimethylamino) -3- (ethylthio) picolinonitrile 3-chloro-5- (dimethylamino) picolinonitrile prepared in Synthesis Example 2-1-9 (0.70 g, 3.85 mmol) was dissolved in N, N-dimethylformamide (14 mL), ethyl mercaptan (0.92 mL, 3.92 mmol) was added, and sodium hydride (55%, 0.19 g) was added under ice-cooling. , 4.29 mmol) and stirred. After returning to room temperature and stirring at the same temperature for 3 hours, water was added to the reaction product, and extracted twice with ethyl acetate.
  • a compound of the present invention represented by the formula (1-3) shown in Table 8 a compound of the present invention represented by the formula (1-4) shown in Table 9, and a compound of the formula (2-2) shown in Table 10 synthesized by the same method as described above.
  • 1 H of the compound of the formula (2-3) shown in Table 11 the compound of the formula (3-2) shown in Table 12, and the compound of the formula (3-3) shown in Table 13 Table 14 shows the NMR data and melting point. In some NMR data, protons of amidine are not detected.
  • Formulation Example 1 [Wettable powder] 30% by weight of compound Clay 30% by weight Diatomaceous earth 35% by weight Sun extract P252 4% by weight (Calcium lignin sulfonate: trade name of Nippon Paper Industries Co., Ltd.) Solpol 8070 1% by weight (Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.) The above components were uniformly mixed and pulverized to obtain a wettable powder.
  • Formulation Example 2 [Powder] 2% by weight of compound 90% clay 7% by weight of talc 1% by weight calcium stearate The above components were uniformly mixed to obtain a powder.
  • Formulation Example 3 [emulsion] 20% by weight of compound N, N-dimethylformamide 20% by weight T-SOL 150 50% by weight (Aromatic solvent: product name of JXTG Energy Corporation) New Calgen CL-H 10% by weight (POE alkyl phenyl ether: product name of Takemoto Yushi Co., Ltd.) The above components were uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 5 Compound 5% by weight Bentonite 40% by weight Talc 10% by weight 43% by weight of clay Sun extract P252 2% by weight (Calcium lignin sulfonate: trade name of Nippon Paper Industries Co., Ltd.) The components were uniformly crushed and mixed, water was added and kneaded well, and the mixture was granulated and dried to obtain granules.
  • Formulation Example 6 [Floable agent] 25% by weight of compound Solpol 7556 5% by weight (POE styryl phenyl ether sulfate: product name of Toho Chemical Industry Co., Ltd.) Propylene glycol 6% by weight Bentonite 1% by weight Xanthan gum 1% aqueous solution 3% by weight Water 60% by weight After premixing the entire amount of the above-mentioned formulation except for a 1% aqueous solution of xanthan gum and an appropriate amount of water, the mixture was pulverized with a wet pulverizer. Thereafter, a 1% aqueous solution of xanthan gum and the remaining water were added to the obtained pulverized product to obtain 100% by weight of a flowable agent.
  • POE styryl phenyl ether sulfate product name of Toho Chemical Industry Co., Ltd.
  • Formulation Example 7 Compound 5% by weight Bentonite 40% by weight Talc 10% by weight 43% by weight of clay Sun extract P252 2% by weight (Calcium lignin sulfonate: trade name of Nippon Paper Industries Co., Ltd.) The components were uniformly crushed and mixed, water was added and kneaded well, and the mixture was granulated and dried to obtain granules.
  • Control efficacy refers to the inhibition of the development of pest invertebrates (including mortality) that significantly reduces feeding.
  • the pest control protection achieved by the compounds is not limited to these species.
  • Compound numbers refer to the compounds in Tables 8-13.
  • Biological test example 1 Cotton aphid (Aphis gossypii) control test (leaf sprinkling treatment) Cucumber leaves were cut to a diameter of 3.5 cm and placed on absorbent cotton moistened with water. Two adult cotton aphids were released here, and bred for 24 hours, after which the adults were removed. 2 mL of a diluted solution of the test compound diluted with water to 200 ppm was sprayed on the cucumber leaves using a spray tower. After air-drying, it was put in a plastic cup together with absorbent cotton, covered, and raised in a constant temperature room at 25 ° C. Five days after the treatment, the animals were observed for life and death, and the mortality was calculated.
  • Biological test example 2 Cotton aphid (Aphis gossypii) control test (root immersion treatment) One cucumber seedling (cotyledon stage) was fixed with urethane so that the root was immersed in a vial (2.7 cm x 6 cm in diameter) containing 10 mL of a drug solution diluted to 3.1 ppm with water. One day after immersion, five first-instar cotton aphid larvae were released and bred in a constant temperature room at 25 ° C. After 5 to 7 days from the release, the insects were examined for viability and abnormalities.
  • the compounds of the present invention 2 3, 7, 14, 20, 29, 45, 46, 48, 51, 53, 55, 62, 85, 91, 103, 105, 106, 108, 111, 120, 170, 173, 180 and 199 showed a mortality of 80% or more.
  • Biological Test Example 3 Tobacco whitefly (Bemisia tabaci) control test (foliage application treatment) Cucumber leaves were cut to a diameter of 6.0 cm and placed on absorbent cotton moistened with water. To this cucumber leaf, 2 mL of a diluted solution of the test compound diluted with water to 200 ppm was sprayed using a spray tower. After air-drying, the cucumber leaves were put in a plastic cup, 20 female adult female whiteflies were released, covered and kept in a constant temperature room at 25 ° C. Five days after the treatment, the animals were observed for life and death, and the mortality was calculated. As a result, the compounds of 13, 156, 196, 204, 209, and 215 showed a mortality of 80% or more.
  • Biological test example 4 Plutella xylostella control test (leaf immersion treatment) The cabbage leaves were cut to a diameter of 7.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to 200 ppm and air-dried. After air-drying, the cabbage leaf pieces were put into a plastic cup, 10 larvae of the third instar larva were released, covered, and raised in a constant temperature room at 25 ° C. Five days after the treatment, the larvae were observed for life and death, and the mortality was calculated.
  • Biological test example 5 Control test for brown planthopper (Nilaparvata lugens) (foliage dipping treatment) Ten rice seedlings were taken, immersed in 20 mL of a test compound solution diluted with water to 200 ppm, and air-dried. After air-drying, it is held in a glass cylinder (4.5 cm x 14 cm) using urethane, and is set up in a plastic cup containing 40 mL of water. To this, 3rd instar larva of brown planthopper was released, covered with a medicine wrapper, and raised in a constant temperature room at 25 ° C. Five days after the treatment, the larvae were observed for life and death, and the mortality was calculated.
  • the compounds of the present invention 1, 2, 3, 4, 5, 7, 10, 11, 14, 16, 18, 19, 20, 26, 29, 31, 42, 43, 44, 45, 46, 48, 49, 50, 51, 53, 55, 59, 61, 85, 86, 90, 91, 98, 103, 106, 152, 170, 176, 181, 215 showed a mortality of 80% or more.
  • Biological test example 6 Control test of Sogatella furcifera (root soaking treatment) Ten rice seedlings are taken, held in a glass cylinder (inner diameter 4.5 cm ⁇ 14 cm) using urethane, and set up in a plastic cup containing 40 mL of a drug solution diluted with water to a concentration of 3.1 ppm. Two days later, ten third-instar larvae of the brown planthopper were released into the glass cylinder, covered with a medicine wrapper, and reared in a constant temperature room at 25 ° C. Seven days after the treatment, the larvae were observed for life and death, and the mortality was calculated. As a result, the compounds 2, 3, 4, 16, 20, 29, 42, 47, 48, 53, and 55 of the present invention exhibited a mortality of 80% or more.
  • Biological test example 7 Spodoptera litura control test (foliage dipping treatment) The cabbage leaves were cut to a diameter of 5.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a test compound diluent diluted with water to 200 ppm and air-dried. After air-drying, cabbage leaf pieces were placed in a plastic cup, and five second instar larvae of the cutworm, Spodoptera litura were released, covered and kept in a constant temperature room at 25 ° C. Five days after the treatment, the larvae were observed for life and death, and the mortality was calculated.
  • the compounds of the present invention 91, 100, 103, 106, 120, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 178, 180, 181, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 219, and 220 showed a mortality of 80% or more.
  • Biological test example 8 Control test of Phyllotreta striolata (foliage dipping treatment) The cabbage leaves were cut to a diameter of 2.8 cm, and the cabbage leaf pieces were immersed in 20 mL of a test compound diluent diluted with water to 200 ppm and air-dried. After air-drying, the cabbage leaf pieces were put into a plastic cup, five adult flea beetles were released, and the cap was covered and kept in a constant temperature room at 25 ° C. Two days after the treatment, adult mortality was observed, and the mortality and the degree of food damage were calculated.
  • the compounds 91, 100, 101, 103, 106, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 181 and 205 of the present invention were 80% or more dead insects. Rate or less than 10%.

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WO2020241606A1 (ja) * 2019-05-27 2020-12-03 日本農薬株式会社 架橋部に窒素原子を有する縮合複素環化合物又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
WO2021177410A1 (ja) * 2020-03-06 2021-09-10 日本化薬株式会社 有害生物防除剤
WO2022259985A1 (ja) * 2021-06-10 2022-12-15 日本化薬株式会社 有害生物防除剤
WO2023088718A1 (en) * 2021-11-19 2023-05-25 Basf Se Bicyclic compounds for the control of invertebrate pests
CN116420726A (zh) * 2022-04-15 2023-07-14 广西壮族自治区农业科学院 一种防治芋田斜纹夜蛾的含噻虫酰胺的杀虫组合物

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