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WO2021215393A1 - Benzamide compound and pest control agent - Google Patents

Benzamide compound and pest control agent Download PDF

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Publication number
WO2021215393A1
WO2021215393A1 PCT/JP2021/015856 JP2021015856W WO2021215393A1 WO 2021215393 A1 WO2021215393 A1 WO 2021215393A1 JP 2021015856 W JP2021015856 W JP 2021015856W WO 2021215393 A1 WO2021215393 A1 WO 2021215393A1
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PCT/JP2021/015856
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French (fr)
Japanese (ja)
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牧野　聖
史也 西尾
裕紀 古川
昌宏 川口
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日本曹達株式会社
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Publication of WO2021215393A1 publication Critical patent/WO2021215393A1/en

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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
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
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    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/24—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
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    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
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    • C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to benzamide compounds and pest control agents. More specifically, the present invention relates to a benzamide compound having excellent insecticidal activity and / or acaricidal activity, which is excellent in safety and can be synthesized industrially advantageously, and a pest control agent containing the benzamide compound as an active ingredient. Regarding.
  • the present application claims priority based on Japanese Patent Application No. 2020-0760557 filed in Japan on April 22, 2020, the contents of which are incorporated herein by reference.
  • Patent Document 1 discloses a compound represented by the following formula (A) or (B) as a compound structurally related to the benzamide compound of the present invention. These compounds have been shown to be used in insecticides and acaricides.
  • An object of the present invention is a benzamide compound having excellent pest control activity, particularly excellent insecticidal activity and / or acaricidal activity, excellent safety, and industrially advantageous synthesis, and a harmful substance containing the benzamide compound as an active ingredient. To provide a biological control agent.
  • Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5-6-membered heteroaryl group.
  • R 1 represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
  • R 2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
  • R 3 represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
  • R 4 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
  • Q indicates a group represented by the formula (Qa) or the formula (Qb).
  • X 1 represents a substituent on the ring, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6. It is an alkylthio group and m represents the number of X 1 and is a chemically acceptable integer from 0 to 4.
  • X 2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
  • Y represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6-membered heteroaryl group.
  • Y' is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6-membered heteroaryl group. Indicates a group. ]
  • a pest control agent containing at least one selected from the group consisting of the compound according to (1) above and a salt thereof as an active ingredient.
  • An insecticide or acaricide containing at least one selected from the group consisting of the compound according to (1) above and a salt thereof as an active ingredient.
  • An ectoparasite control or extermination agent containing at least one selected from the group consisting of the compound according to (1) above and a salt thereof as an active ingredient.
  • the benzamide compound of the present invention can control pests that pose a problem in terms of crops and hygiene.
  • agricultural pests and mites can be effectively controlled at lower concentrations.
  • ectoparasites that harm humans and animals can be effectively controlled.
  • the benzamide compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).
  • the term "unsubstituted” means that there are only parental groups. When there is no description of "substitution” and only the name of the parent group is described, it means “unsubstituted” unless otherwise specified.
  • substituted means that any hydrogen atom of the parent group is substituted with a group (substituent) having the same or different structure as the mother nucleus. Therefore, a “substituent” is another group attached to the parent group.
  • the substituent may be one or two or more. The two or more substituents may be the same or different.
  • C1 to 6 indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the parent group is a butyl group and the substituent is an ethoxy group.
  • the "substituent” is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
  • groups that can be “substituents” include the following groups. Halogeno groups such as fluoro group, chloro group, bromo group, iod group; C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • Alkyl group Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-Pentenyl group, 3-Pentenyl group, 4-Pentenyl group, 1-methyl-2-butenyl group, 2-Methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group, 5-hexenyl group;
  • Ethynyl group 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group , 2-Pentynyl group, 3-Pentynyl group, 4-Pentynyl group, 1-methyl-2-butynyl group, 2-Methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc.
  • C2-6 alkynyl group C3-8 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cubicyl group; C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group; C6-10 aryl groups such as phenyl group and naphthyl group; 3- to 6-membered ring heterocyclyl group;
  • Chloromethyl group chloroethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, perfluoropropane-2-yl group, 1-fluoro-n-butyl group, C1-6 haloalkyl groups such as perfluoro-n-pentyl groups; C1-6 alkoxy C1-6 haloalkyl groups such as 1,1,1,3,3,3-hexafluoro-2-methoxypropane-2-yl group; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C3-6 halocycloalkyl groups such as 1,1-d
  • Cyano group Nitro group; Amino group; C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group; C6-10 arylamino groups such as anilino group and naphthylamino group; Formylamino group; C1-6 alkylcarbonylamino group such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; C1-6 alkyl sulfoxide imino groups such as S, S-dimethyl sulfoxide imino groups;
  • C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio group and propargylthio group; C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoro
  • Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; A tri-C6-10 arylsilyl group such as a triphenylsilyl group. Further, in these "substituents", any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • heterocyclyl group having a 3- to 6-membered ring means that 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom are constituent atoms of the ring (referred to as ring-membered atoms). It is a group produced by removing one hydrogen atom from any ring atom of a 3- to 6-membered cyclic compound, that is, a "3- to 6-membered heterocyclyl compound" contained as (is).
  • the above-mentioned "3- to 6-membered ring heterocyclyl group” is a 3- to 6-membered ring heterocyclyl containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring-membered atoms. It can also be expressed as "base”.
  • the heterocyclyl group may be monocyclic or polycyclic.
  • the polycyclic heterocyclyl group may be any of a saturated alicyclic, an unsaturated alicyclic or an aromatic ring as long as at least one ring is a heterocycle.
  • Examples of the "3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group. ..
  • Examples of the saturated heterocyclyl group having a 3- to 6-membered ring include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group and a dioxanyl group.
  • Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be mentioned.
  • 6-membered ring heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
  • Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered ring heteroaryl group.
  • the "C6 to 10 aryl group” in Ar is a group formed by removing one hydrogen on the ring of a monocyclic or polycyclic aromatic hydrocarbon. Examples of the C6 to 10 aryl group include a phenyl group and a naphthyl group, and preferably a phenyl group.
  • the "5- to 6-membered heteroaryl group" of Ar means that 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom are constituent atoms of the ring (ring member atom). It is a group produced by removing one hydrogen atom from any ring atom of a 5- to 6-membered cyclic aromatic compound contained as (.), That is, a "5- to 6-membered heteroaryl compound".
  • the above-mentioned "5-6-membered heteroaryl group” refers to "a 5- to 6-membered ring containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms" as ring-membered atoms.
  • heteroaryl group It can also be expressed as a "heteroaryl group".
  • the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • a pyrrolyl group a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl
  • 6-membered ring heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
  • a pyrazolyl group, a pyridyl group, or a pyridazinyl group is preferable.
  • halogeno group which is one of X 3 include a fluoro group, a chloro group, a bromo group, an iod group and the like.
  • the "C1 to 6 alkyl group" which is one of X 3 may be a straight chain or a branched chain.
  • Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. , I-Pentyl group, Neopentyl group, 2-Methylbutyl group, 2,2-dimethylpropyl group, i-Hexyl group and the like.
  • C2-6 alkenyl group which is one of X 3 includes vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group and 1-methyl-2.
  • -Propenyl group 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group , 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • C2-6 alkynyl group which is one of X 3 includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group and 1-methyl-2.
  • -Propynyl group 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group , 1-Hexynyl group, 1,1-dimethyl-2-butynyl group and the like.
  • Examples of the "C1 to 6 alkoxy group" which is one of X 3 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, and an i-propoxy group. Examples thereof include an i-butoxy group, an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
  • Examples of the "C2 to 6 alkenyloxy group" which is one of X 3 include a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group and the like.
  • Examples of the "C1 to 6 alkylcarbonyl group" which is one of X 3 include an acetyl group and a propionyl group.
  • Examples of the “C1 to 6 alkoxycarbonyl group” which is one of X 3 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
  • C1-6 alkylthio group which is one of X 3 includes methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like. Can be done.
  • Examples of the "C1 to 6 alkylsulfinyl group" which is one of X 3 include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
  • Examples of the "C1 to 6 alkylsulfonyl group" which is one of X 3 include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • C1-6 alkoxy groups C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group, naphthyl group; cyano Group; can be mentioned.
  • Examples of the "C3-8 cycloalkyl group” which is one of the substituents on the "C6 to 10 aryl group” or the “5- to 6-membered heteroaryl group” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl. Groups, cycloheptyl groups and the like can be mentioned.
  • Examples of the "C6 to 10 aryl group" which is one of X 3 include a phenyl group and a naphthyl group.
  • X 3 which is one of X 3 as "heteroaryl group having 5 to 6-membered ring” include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, a triazolyl group , Oxaziazolyl group, thiadiazolyl group, tetrazolyl group and other 5-membered heteroaryl groups; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group and other 6-membered heteroaryl groups; and the like.
  • Examples of the "C6 to 10 aryloxy group" which is one of X 3 include a phenoxy group and a naphthoxy group.
  • Examples of the "5- to 6-membered heteroaryloxy group" which is one of X 3 include a 5- to 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group.
  • halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, C1-6 alkyl groups such as s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro- C1-6 haloalkyl groups such as n-propyl group, 1-fluoro-n-
  • R a represents a hydrogen atom, a C1 to 6 alkyl group or a C1 to 6 alkoxy group
  • R b is hydrogen. It may represent an atom or a C1-6 alkyl group and R a and R b may be combined to form a C3-6 alkylene group.
  • the "C1-6 alkyl groups" in Ra and R b include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group and i-butyl.
  • Groups, s-butyl groups, t-butyl groups, i-pentyl groups, neopentyl groups, 2-methylbutyl groups, 2,2-dimethylpropyl groups, i-hexyl groups and the like can be mentioned.
  • Examples of the "C1 to 6 alkoxy group” include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group and the like. can.
  • Examples of the "C3 to 6 alkylene group" formed by Ra and R b together include a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • Examples of the group represented by R a R b N-CO- include a carbamoyl group, an N-methylaminocarbonyl group, an N, N-dimethylaminocarbonyl group, an N-ethyl-N-methylaminocarbonyl group, and an N-methoxy-. Examples thereof include an N-methylaminocarbonyl group and a pyrrolidine-1-carbonyl group.
  • R c CONR d- which is one of X 3
  • R c represents a C1 to 6 alkyl group
  • R d represents a hydrogen atom or a C1 to 6 alkyl group.
  • Examples of the “C1 to 6 alkyl groups” in R c and R d include the same as those specifically exemplified in R a and R b.
  • Examples of the group represented by R c CONR d ⁇ include an acetamide group and an N-methylacetamide group.
  • R c ON C (R d )-" which is one of X 3
  • R c represents a C1 to 6 alkyl group.
  • R d represents a hydrogen atom or a C1-6 alkyl group, preferably a hydrogen atom.
  • Examples of the “C1 to 6 alkyl groups” in R c and R d include the same as those specifically exemplified in R a and R b.
  • a halogeno group a substituted or unsubstituted C1 to 6 alkyl group (more preferably).
  • C1-6 alkyl groups optionally substituted with a halogeno group substituted or unsubstituted C1-6 alkoxy groups (more preferably C1-6 alkoxy groups optionally substituted with a halogeno group), substituted or absent.
  • R 1 in formula (I) represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
  • R 2 in formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
  • R 3 in formula (I) represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
  • R 4 in formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
  • Examples of the "substituted thiocarbamoyl group" in R 1 include mono or di-C1-6 alkyl-substituted thiocarbamoyl groups such as methylthiocarbamoyl group, dimethylthiocarbamoyl group and ethyl (methyl) thiocarbamoyl group.
  • halogeno group "substituted or unsubstituted C1-6 alkyl group”, and “substituted or unsubstituted C1-6 alkoxy group” in R 2 , R 3 and R 4 are specifically exemplified in Ar. The same ones can be mentioned.
  • R 1 in formula (I) is preferably a cyano group or an unsubstituted thiocarbamoyl group.
  • R 2 in the formula (I) is preferably a hydrogen atom.
  • R 3 in formula (I) may be a halogeno group; a C1-6 alkyl group optionally substituted with a halogeno group or a C1-6 alkoxy group; an unsubstituted C1-6 alkoxy group; or a cyano group.
  • R 4 in the formula (I) is preferably a hydrogen atom.
  • [Q] Q indicates a group represented by the formula (Qa) or the formula (Qb).
  • Equation (Qa) In equation (Qa), the arrow indicates the bond position.
  • p 1 indicates the number of methylene in parentheses and is 0 or 1, preferably 1
  • p 2 indicates the number of methylene in parentheses and is an integer of 0-2. It is preferably 1.
  • the group represented by the formula (Qa) is represented by the formula (Qa-1) when p 1 is 1 and P 2 is 1.
  • X 1 represents a substituent on the ring, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyl.
  • X Reference numeral 2 is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1 to 6 alkoxy group.
  • halogeno group substituted or unsubstituted C1 to 6 alkyl groups
  • substituted or unsubstituted C1 to 6 alkylthio groups are the same as those specifically exemplified in Ar. be able to.
  • Examples of the "C1 to 6 alkylsulfonyloxy group" in X 1 include a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.
  • halogeno group substituted or unsubstituted C1-6 alkyl group
  • substituted or unsubstituted C1-6 alkoxy group are the same as those specifically exemplified in Ar. be able to.
  • X 2 preferably represents a hydrogen atom, a halogeno group, a hydroxyl group, or a substituted or unsubstituted C1 to 6 alkoxy group, and more preferably a hydrogen atom, a hydroxyl group, or an unsubstituted C1 to 6 alkoxy group.
  • Y is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring hetero. Indicates an aryl group.
  • the "C1 to 6 alkyl group" in Y may be a straight chain or a branched chain.
  • Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group.
  • I-Pentyl group Neopentyl group, 2-Methylbutyl group, 2,2-Dimethylpropyl group, i-Hexyl group and the like.
  • Preferred substituents on the "C1-6 alkyl group" in Y include a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, and a C1-6 alkyl group.
  • halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i.
  • -C1-6 alkoxy groups such as butoxy group and t-butoxy group
  • C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group
  • methylthio group and ethylthio C1 to 6 alkylthio groups such as groups; C1 to 6 alkylsulfinyl groups such as methylsulfinyl group and ethylsulfinyl group; C1 to 6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; trifluoromethylthio group, 2,2 C1-6 haloalkylthio groups such as 2-trifluoroethylthio group; C1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group
  • Aryl group halo-substituted, trifluoromethyl-substituted, or unsubstituted C6-10 aryloxy groups such as phenyloxy group, 4-chlorophenyloxy group, 4-trifluoromethylphenyloxy group; halo-substituted, C1-6 alkyl-substituted , Trifluoromethyl-substituted, or unsubstituted 5- to 6-membered ring heteroaryl group (preferably oxadiazolyl group); halo-substituted, C1 to 6-alkyl substituted, trifluoromethyl-substituted, or unsubstituted 5- to 6-membered ring.
  • Heteroaryloxy group (preferably pyridyloxy group); C1 to 6 alkylcarbonyl groups such as acetyl group and propionyl group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, t- C1 to 6 alkoxycarbonyl groups such as butoxycarbonyl groups; cyano groups can be mentioned.
  • Ra is a hydrogen atom, a C1 to 6 alkyl group or a C1 to 6 alkoxy group.
  • R b represents a hydrogen atom or a C1-6 alkyl group, and R a and R b may be combined to form a C3-6 alkylene group.
  • the "C1-6 alkyl groups" in Ra and R b include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group and i-butyl.
  • Groups, s-butyl groups, t-butyl groups, i-pentyl groups, neopentyl groups, 2-methylbutyl groups, 2,2-dimethylpropyl groups, i-hexyl groups and the like can be mentioned.
  • Examples of the "C1 to 6 alkoxy group” include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group and the like. can.
  • Examples of the "C3 to 6 alkylene group" formed by Ra and R b together include a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • Examples of the group represented by R a R b N- include an amino group, an N-methylamino group, an N, N-dimethylamino group, an N-ethyl-N-methylamino group, and an N-methoxy-N-methylamino group. , Pyrrolidine-1-yl group and the like.
  • R a and R b have the same meanings as described above.
  • R a and R b N-CO- include a carbamoyl group, an N-methylaminocarbonyl group, an N, N-dimethylaminocarbonyl group, an N-ethyl-N-methylaminocarbonyl group, and an N-methoxy-. Examples thereof include an N-methylaminocarbonyl group and a pyrrolidine-1-carbonyl group.
  • R a and R b have the same meanings as described above.
  • the groups represented by R a R b N-SO 2- are sulfamoyl group, N-methylaminosulfonyl group, N, N-dimethylaminosulfonyl group, N-ethyl-N-methylaminosulfonyl group, N-methoxy.
  • -N-Methylaminosulfonyl group, pyrrolidine-1-ylsulfonyl group and the like can be mentioned.
  • R c represents a C1-6 alkyl group and R d is a hydrogen atom or It shows a C1-6 alkyl group.
  • R c and R d include the same as those specifically exemplified in R a and R b.
  • R c CONR d ⁇ include an acetamide group and an N-methylacetamide group.
  • R c SO 2 NR d- which is one of the preferable substituents on "C1 to 6 alkyl groups"
  • R c and R d have the same meanings as described above.
  • Examples of the group represented by R c SO 2 NR d ⁇ include a methyl sulfonamide group and an N-methyl methyl sulfonamide group.
  • R e ON CR f-
  • R e indicates a C1 to 6 alkyl group
  • R f is , Hydrogen atom or C1-6 alkyl group.
  • Examples of the "C1 to 6 alkyl groups" in R e and R f include the same as those specifically exemplified in R a and R b.
  • R e O-N CR f - The group represented by, (methoxyimino) methyl group, (ethoxyimino) methyl group, (methoxyimino) ethyl group, and the like (ethoxyimino) ethyl ..
  • the "C1 ⁇ 6 alkyl group” Ueno more preferred substituents on Y, C1 ⁇ 6 alkylthio group, C1 ⁇ 6 alkylsulfinyl group, C1 ⁇ 6 alkylsulfonyl group or a R a R b N-CO, A group represented by ⁇ (preferably an N-methylaminocarbonyl group) can be mentioned.
  • the "C6 to 10 aryl group" in Y is a group formed by removing one hydrogen on the ring of a monocyclic or polycyclic aromatic hydrocarbon.
  • Examples of the C6 to 10 aryl group include a phenyl group and a naphthyl group, and preferably a phenyl group.
  • Substituents on the C6-10 aryl group include a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted group.
  • Unsubstituted C1-6 alkoxy groups substituted or unsubstituted C2-6 alkenyloxy groups, formyl groups, substituted or unsubstituted C1-6 alkylcarbonyl groups, substituted or unsubstituted C1-6 alkoxycarbonyl groups, substituted or Unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-8 cycloalkyl groups, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 5- to 6-membered heteroaryl group, substituted or unsubstituted C6 to 10 aryloxy group, substituted or unsubstituted 5- to 6-membered ring heteroaryloxy group, hydroxyl group , Nitro group, or cyano group. Specific examples of these
  • the "5- to 6-membered heteroaryl group" in Y means that 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom are constituent atoms of the ring (ring member atom). Is a group produced by removing one hydrogen atom from any ring atom of a 5- to 6-membered cyclic aromatic compound, that is, a "5- to 6-membered heteroaryl compound". ..
  • the above-mentioned "5-6-membered heteroaryl group” refers to "a 5- to 6-membered ring containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms" as ring-membered atoms.
  • heteroaryl group It can also be expressed as a "heteroaryl group".
  • the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • a pyrrolyl group a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl
  • 6-membered ring heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
  • substituent on the heteroaryl group of the 5- to 6-membered ring include the same substituents on the C6 to 10 aryl group described in (2), and a C1 to 6 alkyl group or a halogeno group can be used. It can be preferably mentioned.
  • Y is a substituted or unsubstituted C1 to 6 alkyl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group (preferably a triazolyl group, an oxadiazolyl group, or a pyrimidinyl group). It is preferably a substituted or unsubstituted C1-6 alkyl group, a 5-membered heteroaryl group (preferably a triazolyl group or an oxadiazolyl group) which may be substituted with a C1-6 alkyl group, or a halogeno group. More preferably, it is a 6-membered heteroaryl group (preferably a pyrimidinyl group) which may be substituted with.
  • Equation (Qb) In equation (Qb), the arrow indicates the bond position.
  • p 1 indicates the number of methylene in parentheses and is 0 or 1, preferably 1
  • p 2 indicates the number of methylene in parentheses and is an integer of 0-2. It is preferably 1.
  • the group represented by the formula (Qb) is represented by the formula (Qb-1) when p 1 is 1 and P 2 is 1.
  • Y' is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, Alternatively, a substituted or unsubstituted 5- to 6-membered ring heteroaryl group is shown.
  • substituent on the "C1-6 alkylsulfonyl group” preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, n- C1-6 alkoxy groups such as butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1 ⁇ such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group 6 Haloalkoxy group; C6-10aryl group such as phenyl group and naphthyl group; cyano group;
  • Y' preferably is a substituted or unsubstituted C1 to 6 alkylsulfonyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5- to 6-membered ring heteroaryl group, and is preferably absent.
  • Substituted C1-6 alkylsulfonyl group phenyl group optionally substituted with halogeno group, 5-membered heteroaryl group (preferably oxadiazolyl group) optionally substituted with C1-6 alkyl group, or halogenono More preferably, it is a 6-membered heteroaryl group (preferably a pyridyl group or a pyrimidinyl group) which may be substituted with a group.
  • the compound represented by the formula (I) is preferably represented by the following formula (I-1), (I-2), or (I-3).
  • R 1 , R 2 , R 3 , R 4 , Y, Y', X 2 and X 3 are as described above, and n indicates the number of substituents X 3 on the phenyl group, and 1 Or 2 is shown.
  • Ar' represents a heteroaryl group having a 5- to 6-membered ring.
  • the salt of compound (I) is not particularly limited as long as it is an horticulturally acceptable salt.
  • salts of inorganic acids such as hydrochloric acid and sulfuric acid
  • salts of organic acids such as acetic acid and lactic acid
  • salts of alkali metals such as lithium, sodium and potassium
  • salts of alkaline earth metals such as calcium and magnesium
  • iron, copper and the like Transition metal salts
  • salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, hydrazine and the like can be mentioned.
  • the compound (I) or the salt of the compound (I) is not particularly limited depending on the production method thereof. Further, the salt of compound (I) can be obtained from compound (I) by a known method. For example, the compound (I) of the present invention or the salt of the compound (I) can be obtained by the following production method, specifically, a known production method described in Examples and the like.
  • the benzamide compound of the present invention (hereinafter, may be referred to as "the compound of the present invention") is excellent in the effect of controlling various agricultural pests and pests such as mites that affect the growth of plants.
  • the compound of the present invention is a highly safe compound because it has no phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.
  • the compound of the present invention exhibits an excellent control effect not only on sensitive strains but also on pests of various resistant strains and mites of acaricide-resistant strains.
  • the compound of the present invention is excellent in controlling ectoparasites that are harmful to humans and animals. In addition, it is a highly safe compound because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of a ectoparasite control agent.
  • the compound of the present invention is effective at all developmental stages of the organism to be controlled, and exhibits an excellent control effect on, for example, eggs such as mites and insects, larvae, larvae, pupae, and adults.
  • the pest control agent, or insecticide or acaricide of the present invention contains at least one selected from the benzamide compounds of the present invention as an active ingredient.
  • the amount of the compound of the present invention contained in the pest control agent or the insecticide or acaricide of the present invention is not particularly limited as long as it shows the pest control effect.
  • the pest control agent or insecticide or acaricide of the present invention includes grains; vegetables; root vegetables; potatoes; flowers; fruit trees, foliage plants, tea, coffee, cacao and other trees; grasses; turf.
  • Kind Preferably used for plants such as cotton.
  • the pest control agent or insecticide or acaricide of the present invention includes any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, stalks, stalks, shoots, shoots, cuttings, etc. It may be used for the site.
  • the pest control agent or insecticide or acaricide of the present invention is not particularly limited depending on the species of the plant to which it is applied. Examples of the plant species include the original species, varieties, improved varieties, cultivars, mutants, etc. Examples include hybrids and genetically modified organisms (GMOs).
  • the pest control agent of the present invention can be used for seed treatment, foliage spraying, soil application, water surface application, etc. in order to control various agricultural pests and mites.
  • Lepidoptera butterflies or moths Arctiidae moths, such as the fall webworm (Hyphantria cunea) and the fall webworm (Lemyra imparilis); (b) Bucculatricidae moths, such as Bucculatrix pyrivorella; (c) Moths of the family Carposinidae, such as the peach moth (Carposina sasakii); (d) Crambidae moths, such as the genus Diaphania spp., The genus Pyraustinae (Diaphania indica), the genus Pyraustinae (Diaphania nitidalis); , Awanomeiga (Ostrinia furnacalis), European cornballer (Ostrinia nubilalis), Azukinomeiga (Ostrinia scapulalis); Diatraea grandiosella), Kwa
  • Noctuidae (Agrotis ipsilon), Noctuidae (Agrotis segetum); For example, Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, Cotton ball worm (Helicoverpa zea); The genus (Heliothis spp.), Watakibaga (Heliothis armigera), Fake American tobacco moth (Heliothis virescens); brassicae), Awayoto (Mythimna separata), Futaobikoyaga (Naranga aenescens), Matsukiriga (Panolis japonica), Nisetama nayaga (Peridroma saucia), Soibean looper (Pseudoplusia includens), Irakusagin uwaba (Trichoplusia) (m) Tuft moth (Nolidae) moths, such as Miss
  • Plutellidae moths such as the Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; and other diamondback moths (Plutella xylostella);
  • Pyralidae moths such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Greater wax moth;
  • Moths of the family Stahtmopodidae such as the moth Stahmopoda Stammssa
  • Moths of the clothes moth (Tineidae) such as Iga (Tinea translucens)
  • Tortrix moths such as the Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; for example, the Archips spp.
  • Thripidae for example, Thripidae (Ponticulothrips diospyrosi);
  • Thripidae for example Frankliniella spp., Thripidae thripidae, Frankliniella occidentalis; for example, Thrips spp. Thrips palmi, Thrips tabaci;
  • Others Thripidae (Heliothrips haemorrhoidalis), Western flower thrips (Scirtothrips dorsalis).
  • Leafhoppers (Cicadellidae), for example, Empoasca spp., Leafhoppers (Empoasca fabae), Leafhoppers (Empoasca nipponica), Chanomidorihimeyokobai (Empoasca onukii), Leafhopper (Empoasca sakaii); Others, Leafhopper (Arboridia apicalis), Empoasca (Balclutha saltuella), Leafhopper (Epiacanthus stramineus), Leafhopper (Macrosteles striifrons) ).
  • C Heteroptera
  • Riptortus clavatus of the family Alydidae for example
  • Miridae for example, Halticus insularis, Lygus lineolaris, Cotton-free hopper (Psuedatomoscelis seriatus), Nagamugi lygus (Stenodema sibiricum), Akasuji lygus (Stenodema sibiricum) ), Rice lygus (Trigonotylus caelestialium);
  • Stink bugs for example, Nezara spp., Stink bug (Nezara antennata), Southern green stink bug (Nezara viridula); for example, Stink bug genus (Eysarcoris spp.) , Stink bug (Eysarcoris aeneus), Stink bug (Eysarcoris lewisi), Stink bug (Eysarcoris ventralis), Others, Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum) Halyomorpha halys), stink bug (Piezodorus hybneri), stink bug (Plautia crossota), stink bug (Scotinophora lurida); (f) Of the red bug family (Pyrrhocoridae), for example, the red bug (Dysdercus cingulatus); (g) Of the leaf-
  • (D) Sternorrhyncha (a) Adelgidae, for example, Larch aphid (Adelges laricis); (b) Whitefly family (Aleyrodidae), for example, Bemisia spp., Silverleaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Other whitefly (Aleurocanthus spiniferus), Whitefly (Dialeurodes citri), Greenhouse whitefly (Trialeuro des vaporariorum); (c) Aphididae, for example, Aphis spp., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii ), European apple aphid (Aphis pomi), Niwatokoa aphid (Aphis sambuci), Yukiyanagi aphid (Aphis spiraecola); For
  • Coccidae for example, Ceroplastes spp., Ceroplastes ceriferus, Ceroplastes rubens;
  • Diaspididae Pseudaulacaspis spp., Pseudaulacaspis pentagona, Pseudaulacaspis prunicola; for example, Unaspis spp.
  • Pests of the suborder Polyphaga (a) Anobiidae, for example, Lasioderma serricorne; (b) Attelabidae, for example, Byctiscus betulae, Rhynchites heros; (c) Lyctus brunneus of the family Lyctus brunneus; (d) Cylas formicarius of the family Curculionidae (Brentidae); (e) Of the jewel beetle family (Buprestidae), for example, the jewel beetle (Agrilus sinuatus); (f) Cerambycidae, for example, Anoplophora malasiaca, Monocohamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (g) Chrysomelidae, eg, Bruchus spp., Pea weevil (Bruchus pisorum), Broad bean weevil (Bruchus rufiman
  • Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); ); Others, Aulacophora femoralis, Callosobruchuschinensis, Cassida nebulosa, Chaetocnema concinna, Colorado leaf beetle (Leptinotarsa decemlineata), Inekubihosohamushi (Oul) Broad beetle (Psylliodes angusticollis);
  • Agromyzidae for example, Agromyzidae (Liriomyza spp.), Agromyzidae (Liriomyza bryoniae), Agromyzidae (Liriomyza chinensis), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza sativae), Agromyzidae (Liriomyza sativae) Others, Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae); (b) Anthomyiidae, eg, Delia spp., Delia platura, Delia radicum; and other sugar beet, Pegomya cunicularia; (c) Drosophilidae, for example, Drosophil
  • Nematocera (a) Cecidomyiidae, for example, Soybean Cecidomyiidae, Sorghum sorghicola, Hessian fly (Mayetiola destructor), Mugia caterpillar (Sitodiplosis mosellana).
  • Orthoptera pests Locustaceae (Acrididae), for example, the genus Schistocerca spp., American locust (Schistocerca americana), desert locust (Schistocerca gregaria); Australia Tobibatta (Chortoicetes terminifera), Sydney Inago (Dociostaurus maroccanus), Tonosamabatta (Locusta migratoria), Brown Inago (Locustana pardalina), Akatobibatta (Nomadacris septemfasciata), Kobaneinago (Oxya yezoensis) (b) Cricket family (Gryllidae), such as European house cricket (Acheta domestica), cricket (Teleogryllus emma); (c) Mole cricket (Gryllotalpidae), for example, mole cricket (Gryllotalpa orientalis); (d) Of the Bush cricket family (Tettigoniidae), for example, Tachy
  • Mites (Acari) (A) Acaridida of the order Astigmata (a) Acaridae mites, such as Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis;
  • B Prostigmata prostigmata (Actinedida)
  • Spider mite Tetranychidae mites, such as Bryobia spp., Clover mite (Bryobia praetiosa), fake clover mite (Bryobia rubrioculus); for example, Eotetranychus spp.
  • Eotetranychus asiaticus Anzu spider mite (Eotetranychus boreus), Eotetranychus celtis, Michinoku spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus kankitus) (Eotetranychus smithi), Suginami spider mite (Eotetranychus suginamensis), walnut spider mite (Eotetranychus uncatus); Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus perseae), Ezosugi spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), rice spider mite (Oligonychus shinkajii) Panonychus citr
  • Gasgomori spider mite (Shizotetranychus longus), Susukisugomori spider mite (Shizotetranychus miscanthi), Himesasa spider mite (Shizotetranychus recki), Yanagi spider mite (Shizotetranychus schizopus);
  • Tick of the family Tenuipalpidae for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus phoenicis, Brevipalpus phoenicis russulus), Brevipalpus californicus;
  • Tenuipalpus spp. Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; Other, pineapple zhizhilashviliae;
  • Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation.
  • Aceria paradianthi Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes chibaensis, Eriophyes chibaensis );
  • Tomato sabi tick Aculops lycopersici
  • Mikan sabi tick Aculops pelekassi of the genus Acurops (Aculops spp.);
  • Others Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepirimerus vitis, Epitrimerus pyri, Paraphytopa docari ), Phyllocotruta citri;
  • Tarsonemidae mites such as Tarsonemus spp., Tarsonemus bilobatus, Tarsonemus waitei
  • Others Cyclamen tarsonemidae
  • the pest control agent or insecticide or acaricide of the present invention may contain components other than the compound of the present invention.
  • other components include known carriers used for formulation.
  • insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
  • Acetylcholinesterase (AChE) inhibitor (carbamate type) Aranicarb, Aldicarb, Bendiocarb, Benfracarb, Butocarboxim, Butoxycarboxym, Carbaryl, Carbofuran, Carbosulfan, Ethiophenate, Phenocalve, Formethanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamil, Pyrimicurve, Propoxul Thiophanox, Triazamate, Trimetacarb, XMC, Kisilylcarb.
  • AChE Acetylcholinesterase
  • Acetylcholinesterase (AChE) inhibitor organophosphorus
  • ⁇ -bifenthrin biopermethrin, chloropralesrin, dimefluthrin, fenfurthrin, fenpyritrin, flufenprox, heptafluthrin, meperfluthrin, ⁇ -methfurthrin, monfluorothrin, ⁇ -monfluorothrin, trans-permethrin, profluthrin , Protrifenbut, ⁇ -tefluthrin, terraretrin, tetramethylfluthrin; bioetanomethrin.
  • DDTs Sodium channel modulators
  • Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradiflon; triflumesopirim. Nichiazine; dichloromethane, dichloromethane. (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulator Spinosad, spinosad.
  • Chitin biosynthesis inhibitor type 0 Bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflumron. Full Azlon.
  • Chitin biosynthesis inhibitor type 1 Buprofezin.
  • Cyromazine a molting inhibitor.
  • Molting hormone (ecdysone) receptor agonist chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
  • Anthelmintic (a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, fevantel, netobimin, thiophanate, thiabendazole, cambendazole; (b) Salicylanilides: closantel, oxyclozanide, lafoxanide, niclosamide; (c) Substituted phenolic system: nitroxynyl, nitroscanate; (d) Pyrimidines: Pyrantel, Morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) Tetrahydropyrimidines: Praziquantel, Epsiprantel; (g) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demidit
  • Nucleic acid biosynthesis inhibitor (a) RNA polymerase I Inhibitors: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M, Oxadixil, Closilacon, Offrace; (b) Adenosine deaminase inhibitors: bupirimate, dimethilimol, etilimol; (c) DNA / RNA synthesis inhibitors: himexazole, octylinone; (d) DNA topoisomerase II inhibitor: oxolinic acid.
  • RNA polymerase I Inhibitors Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M, Oxadixil, Closilacon, Offrace
  • Adenosine deaminase inhibitors bupirimate, dimethilimol, etilimol
  • DNA / RNA synthesis inhibitors himexazole, octylinone
  • Mitotic and fission inhibitors (a) ⁇ -tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, dietofencarb, zoxamide, etaboxam; (b) Cell division inhibitor: pencyclon; (c) Spectrin-like protein delocalization inhibitor: fluoricolide.
  • Respiratory inhibitor (a) Complex I NADH Oxidoreductase Inhibitors: Diflumetrim, Torphenpyrad; (b) Complex II succinate dehydrogenase inhibitor: benodanyl, flutranyl, mepronil, isofetamide, fluopirum, fenfuram, flumecyclox, carboxin, oxycarboxin, thyfluzamide, benzobindiflupill, bixaphen, fluxapyroxado , Flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan, boscalide, pyraziflumid; (c) Complex III Ubiquinol Oxidase Qo Inhibitors: Azoxystrobin, Spiderxtrobin, Kumethoxystrobin, Enokistrobin, Fluphenoxystrobin, Picoxystrobin, Pyraoxystrobin, Pyracrostrobin, Pyrametostrobin, triclopyricalve, cres
  • Methionine biosynthesis inhibitors andprim, cyprodinyl, mepanipyrim, pyrimethanyl;
  • Protein synthesis inhibitors Blasticidin-S, casugamycin, casugamycin hydrochloride, streptomycin, oxytetracycline.
  • Signal transduction inhibitor (a) Signal transduction inhibitors: quinoxyphen, proquinazide; (b) MAP / histidine kinase inhibitors in osmotic signaling: fenpicronyl, fludioxonyl, clozolineate, iprodion, procymidone, vinclozoline.
  • Lipid and cell membrane synthesis inhibitor (a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenphos, pyrazophos, isoprothiolane; (b) Lipid peroxidizers: biphenyl, chloroneb, dichloran, quintozen, technazen, toluclophosmethyl, etridiazole; (c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb Josetilate, prothiocarb; (d) Pathogens Microorganisms that disrupt cell membranes: Bacillus bacillus, Bacillus bacillus QST713, Bacillus bacillus FZB24, Bacillus bacillus MBI600, Bacillus chinensis D747; (e) Agent that disturbs cell membranes: Extract of Gosei Kayupte (tea tree), Li
  • Cell membrane sterol biosynthesis inhibitor (a) Demethylation inhibitor at position C14 in sterol biosynthesis: trifoline, pyrifenox, pyrisoxazole, phenalimol, fluconazole, nuarimol, imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloraz, triflumizole , Biniconazole, azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole,
  • Trehalase inhibitor Validamycin
  • Chitin synthase inhibitors polyoxin, polyoxolim
  • Cellulose Synthetic Enzyme Inhibitors Dimethmorph, Fulmorph, Pyrimorph, Bench Avaricarb, Iprovaricarb, Torprocarb, Variphenalate, Mandipropamide.
  • Melanin biosynthesis inhibitor (a) Melanin biosynthesis reductase inhibitor: fusalide, pyroquilon, tricyclazole; (b) Dehydrating enzyme inhibitors of melanin biosynthesis: calpropamide, diclosimet, phenoxanyl.
  • Host plant resistance inducer (a) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl; (b) Others: probenazole, thiazinyl, isothianil, laminarin, Reynoutria sachalinensis extract.
  • Agents of unknown activity simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.
  • Agents with multi-action points Copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbum, mancozeb, maneb, Man copper, methylam, polycarbamate, propineb, tiram, dineb, dilam, captan, captahole, folpet, chlorotalonyl, diclofluanide, trillfluanide, guazatin, guazatin acetate, iminoctadine triacetate, iminoctadine albecil Iminoctadine trial besilate, anilazine, dithianone, quinomethionate, fluorimide.
  • plant growth regulators that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
  • the ectoparasite control or extermination agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
  • the ectoparasite control or extermination agent of the present invention is excellent in the effect of controlling ectoparasites that are harmful to humans and animals.
  • Ectoparasites parasitize the body and skin of host animals, especially warm-blooded animals and fish. Specifically, it parasitizes the back, armpits, lower abdomen, inner thigh, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, flesh flies, and worms.
  • the host animals to be treated with the ectoparasite control or extermination agent of the present invention include pet animals such as dogs and cats; pet birds; livestock such as cows, horses, pigs and sheep; warm-blooded animals such as poultry; Can be mentioned.
  • Other examples include fish such as salmon, trout, blowfish, carp and goldfish; insects such as honeybees, stag beetles and beetles; Ectoparasites parasitize in and on host animals, especially warm-blooded animals. Specifically, it parasitizes the back, armpits, lower abdomen, inner thigh, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal.
  • fish such as salmon, trout, blowfish, carp and goldfish
  • insects such as honeybees, stag beetles and beetles
  • Ectoparasites parasitize in and on host animals, especially warm-blooded animals. Specifically, it parasitizes the back, armpits, lower abdomen, inner thigh, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal.
  • the ectoparasite control or extermination agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration).
  • a method of orally administering to an animal by mixing tablets, capsules, feed, etc . a method of administering to an animal by an immersion liquid, a suppository, an injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oily or A method of locally administering an aqueous solution by spraying, pore-on, spot-on, etc .; Kneading an ectoparasite control agent into a resin, molding the kneaded product into an appropriate shape such as a collar, ear tag, etc. A method of wearing and locally administering;
  • ectoparasites that can be controlled or exterminated by the ectoparasite control or extermination agent of the present invention are shown below.
  • Mites Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodidae mites, cucumber mites Insect-parasitic mites such as Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodixidae Demodixidae mites, Trombiculidae mites, and mulberry mites. ..
  • Flea eyes Sephonaptera
  • Human flea (Pulicidae) fleas such as dog fleas (Ctenocephalides spp.), Dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis); Fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae (Leptopsyllidae).
  • Hemiptera Diptera mosquitoes, Culicidae mosquitoes, Simuliidae mosquitoes, Ceratopogonidae mosquitoes, Tabanidae mosquitoes, Muscidae flies, Glossinidae Glossinidae, Glossinidae flies, Hipboscidae flies, Calliphoridae flies, Oestridae flies.
  • (Formation example 1: wettable powder) 40 parts of the compound of the present invention, 53 parts of diatomaceous soil, 4 parts of higher alcohol sulfate ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder having 40% of the active ingredient.
  • Formation example 6 Granules
  • Five parts of the compound of the present invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure to obtain granules. This type of granule can be used by mixing with animal food.
  • Formation example 7 Injectable agent
  • An injection is obtained by uniformly mixing 0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil, and then filtering and sterilizing with a sterilization filter.
  • a poreon agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.
  • Spray agent A spray agent is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.
  • Methyl 4-amino-5-cyano-2- (trifluoromethyl) benzoate (5.0 g) was dissolved in hydrobromic acid (68 ml), which was then ice-cooled with water (14 ml) and sodium nitrite. (4.2 g) was added, and the mixture was stirred for 1 hour. Then, water (68 ml) and copper (I) bromide (8.8 g) were added thereto, and the mixture was stirred overnight at room temperature. Ammonia water was poured into the obtained liquid, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate.
  • Table 1 shows the combinations of Y, R 1 , R 2 , R 3 , R 4 , X 2 and (X 3 ) n in the formula (I-1) and the physical characteristics of the compounds represented by the combinations. ..
  • Table 2 shows the combinations of Y', R 1 , R 2 , R 3 , R 4 and (X 3 ) n in the formula (I-2) and the physical characteristics of the compounds represented by the combinations.
  • Table 3 shows the combinations of Y, R 1 , R 2 , R 3 , R 4 , X 2 and Ar'in the formula (I-3) and the physical characteristics of the compounds represented by the combinations.
  • N in formulas (I-1) and (I-2) indicates the number of substituents X 3 on the phenyl group.
  • the melting point (mp) or the property is shown.
  • Ph indicates a phenyl group
  • Me indicates a methyl group
  • Et indicates an ethyl group.
  • Efficacy test against armyworm Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass.
  • the corn leaf pieces were immersed in the diluted solution for 30 seconds.
  • the corn leaf pieces were placed in a petri dish, and 5 second-instar larvae of Mythimna separata were released to prepare an emulsion treatment group.
  • the solvent control solution was diluted with water at the same rate as the emulsion (I), and the corn leaf pieces were immersed therein for 30 seconds.
  • the corn leaf pieces were placed in a petri dish, and 5 second-instar larvae of Mythimna separata were released, and the petri dish was used as a solvent control group.
  • Randomly selected compounds of the present invention exert the above-mentioned effects. Therefore, the compounds of the present invention, including compounds that could not be exemplified, control pests, especially insecticide, acaricide, and ectoparasites. It can be understood that it is a compound that has effects such as insect control, does not cause chemical damage to plants, and has little toxicity to humans, livestock and fish, and has little effect on the environment.
  • the benzamide compound of the present invention can control pests that pose a problem in terms of crops and hygiene.
  • agricultural pests and mites can be effectively controlled at lower concentrations.
  • ectoparasites that harm humans and animals can be effectively controlled.

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Abstract

Provided is the compound, or a salt thereof, represented in formula (I). (In formula (1): Ar indicates a C6-10 aryl group, etc.; R1 indicates a cyano group, a thiocarbamoyl group, etc.; R2 indicates a hydrogen atom, etc.; R 3 indicates a C1-6 alkyl group, etc.; R4 indicates a hydrogen atom group, etc.; Q indicates the group represented by formula (Qb), etc.; the arrow indicates a bond position; p 1 indicates the number of methylenes inside the parentheses, and is 0 or 1; p2 indicates the number of methylenes inside the parentheses, and is any integer from 0 to 2; X1 is a halogen group, a C1-6 alkyl group, etc.; m indicates the number of X1, and is any integer from 0-4 that is chemically permissible; and Y' indicates a C1-6 alkyl group, a C1-6 alkyl sulfonyl group, etc.)

Description

ベンズアミド化合物および有害生物防除剤Benzamide compounds and pest control agents
　本発明は、ベンズアミド化合物および有害生物防除剤に関する。より詳細に、本発明は、優れた殺虫活性および／または殺ダニ活性を有し、安全性に優れ、且つ工業的に有利に合成できるベンズアミド化合物、ならびにこれを有効成分として含有する有害生物防除剤に関するに関する。
　本願は、２０２０年４月２２日に、日本に出願された特願２０２０－０７６０５７号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to benzamide compounds and pest control agents. More specifically, the present invention relates to a benzamide compound having excellent insecticidal activity and / or acaricidal activity, which is excellent in safety and can be synthesized industrially advantageously, and a pest control agent containing the benzamide compound as an active ingredient. Regarding.
The present application claims priority based on Japanese Patent Application No. 2020-0760557 filed in Japan on April 22, 2020, the contents of which are incorporated herein by reference.
　本発明のベンズアミド化合物に構造上関連する化合物として、特許文献１は、下記式（A）または（B）で表される化合物を開示している。これらの化合物は、殺虫殺ダニ剤に用いることが示されている。 Patent Document 1 discloses a compound represented by the following formula (A) or (B) as a compound structurally related to the benzamide compound of the present invention. These compounds have been shown to be used in insecticides and acaricides.
Figure JPOXMLDOC01-appb-C000003
Figure JPOXMLDOC01-appb-C000003
ＷＯ２０１５／０３２２８０Ａ１WO2015 / 032280A1
　本発明の課題は、有害生物防除活性、その中でも特に殺虫活性および／または殺ダニ活性に優れ、安全性に優れ、且つ工業的に有利に合成できるベンズアミド化合物、ならびにこれを有効成分として含有する有害生物防除剤を提供することである。 An object of the present invention is a benzamide compound having excellent pest control activity, particularly excellent insecticidal activity and / or acaricidal activity, excellent safety, and industrially advantageous synthesis, and a harmful substance containing the benzamide compound as an active ingredient. To provide a biological control agent.
　上記課題を解決すべく検討した結果、以下の形態を包含する本発明を完成するに至った。
（１）　式(I)で表される化合物またはその塩。 As a result of studies for solving the above problems, the present invention including the following forms has been completed.
(1) A compound represented by the formula (I) or a salt thereof.
Figure JPOXMLDOC01-appb-C000004
Figure JPOXMLDOC01-appb-C000004
　〔式（I）中、
　Ａｒは、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示し、
　Ｒ1は、シアノ基、または置換若しくは無置換のチオカルバモイル基を示し、
　Ｒ2は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示し、
　Ｒ3は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示し、
　Ｒ4は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示し、
　Ｑは、式（Qa）または式（Qb）で表わされる基を示す。 [In equation (I),
Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5-6-membered heteroaryl group.
R 1 represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
R 2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
R 3 represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
R 4 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
Q indicates a group represented by the formula (Qa) or the formula (Qb).
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
　前記式（Qa）および式（Qb）中、
　矢印は結合位置を示し、
　ｐ1は、括弧内のメチレンの数を示し且つ０または１であり、
　ｐ2は、括弧内のメチレンの数を示し且つ０～２のいずれかの整数であり、
　Ｘ1は、環上の置換基を示し、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、置換若しくは無置換のＣ１～６アルキルスルホニルオキシ基、または置換若しくは無置換のＣ１～６アルキルチオ基であり、
　ｍは、Ｘ1の数を示し且つ化学的に許容される０～４のいずれかの整数であり、
　Ｘ2は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示し、
　Ｙは、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示し、
　Ｙ’は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示す。〕 In the above equations (Qa) and (Qb),
The arrow indicates the connection position,
p 1 indicates the number of methylene in parentheses and is 0 or 1.
p 2 indicates the number of methylene in parentheses and is an integer of 0 to 2.
X 1 represents a substituent on the ring, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6. It is an alkylthio group and
m represents the number of X 1 and is a chemically acceptable integer from 0 to 4.
X 2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
Y represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6-membered heteroaryl group.
Y'is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6-membered heteroaryl group. Indicates a group. ]
（２）　前記（１）に記載の化合物、およびその塩からなる群から選ばれる少なくとも１つを有効成分として含有する、有害生物防除剤。
（３）　前記（１）に記載の化合物、およびその塩からなる群から選ばれる少なくとも１つを有効成分として含有する、殺虫若しくは殺ダニ剤。
（４）　前記（１）に記載の化合物、およびその塩からなる群から選ばれる少なくとも１つを有効成分として含有する、外部寄生虫防除もしくは駆除剤。 (2) A pest control agent containing at least one selected from the group consisting of the compound according to (1) above and a salt thereof as an active ingredient.
(3) An insecticide or acaricide containing at least one selected from the group consisting of the compound according to (1) above and a salt thereof as an active ingredient.
(4) An ectoparasite control or extermination agent containing at least one selected from the group consisting of the compound according to (1) above and a salt thereof as an active ingredient.
　本発明のベンズアミド化合物は、農作物や衛生面で問題となる有害生物を防除することができる。特に農業害虫およびダニ類をより低濃度で効果的に防除することができる。さらに、人畜を害する外部寄生虫を効果的に防除することができる。 The benzamide compound of the present invention can control pests that pose a problem in terms of crops and hygiene. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, ectoparasites that harm humans and animals can be effectively controlled.
〔ベンズアミド化合物〕
　本発明のベンズアミド化合物は、式（I）で表される化合物（以下、化合物（I）と表記することがある。）または化合物（I）の塩である。 [Benzamide compound]
The benzamide compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
　本発明において、用語「無置換（unsubstituted）」は、母核となる基のみであることを意味する。「置換」との記載がなく母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換」の意味である。
　一方、用語「置換(substituted)」は、母核となる基のいずれかの水素原子が、母核と同じまたは異なる構造の基（置換基）で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は１つであってもよいし、２つ以上であってもよい。２つ以上の置換基は同じものであってもよいし、異なるものであってもよい。 In the present invention, the term "unsubstituted" means that there are only parental groups. When there is no description of "substitution" and only the name of the parent group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the parent group is substituted with a group (substituent) having the same or different structure as the mother nucleus. Therefore, a "substituent" is another group attached to the parent group. The substituent may be one or two or more. The two or more substituents may be the same or different.
　「Ｃ１～６」などの用語は、母核となる基の炭素原子数が１～６個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、エトキシブチル基は、母核となる基がブチル基であり、置換基がエトキシ基であるので、Ｃ２アルコキシＣ４アルキル基に分類する。 Terms such as "C1 to 6" indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the parent group is a butyl group and the substituent is an ethoxy group.
　「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。
　「置換基」となり得る基の具体例としては、以下の基を挙げることができる。
　フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；
　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；
　ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などのＣ２～６アルケニル基； The "substituent" is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
Halogeno groups such as fluoro group, chloro group, bromo group, iod group;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. Alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-Pentenyl group, 3-Pentenyl group, 4-Pentenyl group, 1-methyl-2-butenyl group, 2-Methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group, 5-hexenyl group;
　エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などのＣ２～６アルキニル基；
　シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、キュバニル基などのＣ３～８シクロアルキル基；
　２－シクロプロペニル基、２－シクロペンテニル基、３－シクロヘキセニル基、４－シクロオクテニル基などのＣ３～８シクロアルケニル基；
　フェニル基、ナフチル基などのＣ６～１０アリール基；
　３～６員環のヘテロシクリル基； Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group , 2-Pentynyl group, 3-Pentynyl group, 4-Pentynyl group, 1-methyl-2-butynyl group, 2-Methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc. C2-6 alkynyl group;
C3-8 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cubicyl group;
C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group;
C6-10 aryl groups such as phenyl group and naphthyl group;
3- to 6-membered ring heterocyclyl group;
　水酸基；　オキソ基；
　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；
　ビニルオキシ基、アリルオキシ基などのＣ２～６アルケニルオキシ基；
　エチニルオキシ基、プロパルギルオキシ基などのＣ２～６アルキニルオキシ基；
　フェノキシ基、ナフトキシ基などのＣ６～１０アリールオキシ基；
　３～６員環のヘテロシクリルオキシ基；
　ヒドロキシメチル基、ヒドロキシエチル基などのヒドロキシＣ１～６アルキル基；
　メトキシメチル基、エトキシメチル基などのＣ１～６アルコキシアルキル基；
　メトキシメトキシ基、エトキシメトキシ基などのＣ１～６アルコキシＣ１～６アルコキシ基； Hydroxy group; oxo group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group;
C2-6 alkenyloxy groups such as vinyloxy groups and allyloxy groups;
C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
3- to 6-membered ring heterocyclyloxy group;
Hydroxy C1-6 alkyl groups such as hydroxymethyl group and hydroxyethyl group;
C1-6 alkoxyalkyl groups such as methoxymethyl group and ethoxymethyl group;
C1-6 alkoxy groups such as methoxymethoxy group and ethoxymethoxy group C1-6 alkoxy groups;
　カルボキシル基；
　ホルミル基；　アセチル基、プロピオニル基などのＣ１～６アルキルカルボニル基；
　ホルミルオキシ基；　アセチルオキシ基、プロピオニルオキシ基、ｎ－プロピルカルボニルオキシ基、ｉ－プロピルカルボニルオキシ基などのＣ１～６アルキルカルボニルオキシ基；
　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基；
　ベンゾイルなどのＣ６～１０アリールカルボニル基； Carboxyl group;
Formyl group; C1-6 alkylcarbonyl group such as acetyl group, propionyl group;
Formyloxy group; C1-6 alkylcarbonyloxy group such as acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
C6-10 arylcarbonyl groups such as benzoyl;
　クロロメチル基、クロロエチル基、ジフルオロメチル基、トリフルオロメチル基、２，２，２－トリフルオロエチル基、パーフルオロエチル基、パーフルオロプロパン－２－イル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；
　１，１，１，３，３，３－ヘキサフルオロ－２－メトキシプロパン－２－イル基などのＣ１～６アルコキシＣ１～６ハロアルキル基；
　２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などのＣ２～６ハロアルケニル基；
　４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などのＣ２～６ハロアルキニル基；
　１，１－ジフルオロシクロプロピル基、３，３－ジフルオロシクロブチル基などのＣ３～６ハロシクロアルキル基；
　ジフルオロメトキシ基、トリフルオロメトキシ基、２，２，２－トリフルオロエトキシ基、１，１，２，２－テトラフルオロエトキシ基、２，２，３，３，３－ペンタフルオロプロポキシ基、４，４，４－トリフルオロブトキシ基、（１，１，１，３，３，３－ヘキサフルオロプロパン－２－イル）オキシ基などのＣ１～６ハロアルコキシ基；
　２－クロロプロペニルオキシ基、３－ブロモブテニルオキシ基などのＣ２～６ハロアルケニルオキシ基；
　クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基などのＣ１～６ハロアルキルカルボニル基； Chloromethyl group, chloroethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, perfluoropropane-2-yl group, 1-fluoro-n-butyl group, C1-6 haloalkyl groups such as perfluoro-n-pentyl groups;
C1-6 alkoxy C1-6 haloalkyl groups such as 1,1,1,3,3,3-hexafluoro-2-methoxypropane-2-yl group;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group;
C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C3-6 halocycloalkyl groups such as 1,1-difluorocyclopropyl group, 3,3-difluorocyclobutyl group;
Difluoromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2,2,3,3,3-pentafluoropropoxy group, 4, C1-6 haloalkoxy groups such as 4,4-trifluorobutoxy group, (1,1,1,3,3,3-hexafluoropropan-2-yl) oxy group;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;
　シアノ基；　ニトロ基；　アミノ基；
　メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのＣ１～６アルキルアミノ基；
　アニリノ基、ナフチルアミノ基などのＣ６～１０アリールアミノ基；
　ホルミルアミノ基；　アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基などのＣ１～６アルキルカルボニルアミノ基；
　メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、ｎ－プロポキシカルボニルアミノ基、ｉ－プロポキシカルボニルアミノ基などのＣ１～６アルコキシカルボニルアミノ基；
　Ｓ，Ｓ－ジメチルスルホキシイミノ基などのＣ１～６アルキルスルホキシイミノ基； Cyano group; Nitro group; Amino group;
C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
Formylamino group; C1-6 alkylcarbonylamino group such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
C1-6 alkyl sulfoxide imino groups such as S, S-dimethyl sulfoxide imino groups;
　カルバモイル基；Ｎ’－ヒドロキシカルバムイミドイル基；
　メチルアミノカルボニル基、ジメチルアミノカルボニル基、エチルアミノカルボニル基、ｉ－プロピルアミノカルボニル基などのＣ１～６アルキルアミノカルボニル基；
　イミノメチル基、（１－イミノ）エチル基、（１－イミノ）－ｎ－プロピル基などのイミノＣ１～６アルキル基；
　ヒドロキシイミノメチル基、（１－ヒドロキシイミノ）エチル基、（１－ヒドロキシイミノ）プロピル基などのヒドロキシイミノＣ１～６アルキル基；
　メトキシイミノメチル基、（１－メトキシイミノ）エチル基などの（Ｃ１～６アルコキシイミノ）Ｃ１～６アルキル基；
　アセトキシイミノメチル基などの（Ｃ１～６アルキルカルボニルオキシイミノ）Ｃ１～６アルキル基； Carbamoyl group; N'-hydroxycarbamimideyl group;
C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group;
Imino C1-6 alkyl groups such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group;
Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group;
(C1-6 alkoxyimino) C1-6 alkyl groups such as methoxyiminomethyl group, (1-methoxyimino) ethyl group;
(C1-6 alkylcarbonyloxyimino) C1-6 alkyl groups such as acetoxyiminomethyl groups;
　メルカプト基；
　メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔ－ブチルチオ基などのＣ１～６アルキルチオ基；
　トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基；
　ビニルチオ基、アリルチオ基などのＣ２～６アルケニルチオ基；
　エチニルチオ基、プロパルギルチオ基などのＣ２～６アルキニルチオ基；
　メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などのＣ１～６アルキルスルフィニル基；
　トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；
　アリルスルフィニル基などのＣ２～６アルケニルスルフィニル基；
　プロパルギルスルフィニル基などのＣ２～６アルキニルスルフィニル基；
　メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などのＣ１～６アルキルスルホニル基；
　トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；
　アリルスルホニル基などのＣ２～６アルケニルスルホニル基；
　プロパルギルスルホニル基などのＣ２～６アルキニルスルホニル基；
　チオカルバモイル基；
　イミノ（メチルチオ）メチル基などのイミノ（Ｃ１～６アルキルチオ）メチル基；
　ペンタフルオロスルファニル基； Mercapto group;
C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as vinylthio groups and allylthio groups;
C2-6 alkynylthio groups such as ethynylthio group and propargylthio group;
C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups;
C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups;
C2-6 alkenylsulfonyl groups such as allylsulfonyl groups;
C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups;
Thiocarbamoyl group;
Imine (C1-6 alkylthio) methyl groups such as imino (methylthio) methyl groups;
Pentafluorosulfanil group;
　トリメチルシリル基、トリエチルシリル基、ｔ－ブチルジメチルシリル基などのトリＣ１～６アルキルシリル基；
　トリフェニルシリル基などのトリＣ６～１０アリールシリル基。
　また、これらの「置換基」は、前記置換基中のいずれかの水素原子が、異なる構造の基で置換されていてもよい。 Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
A tri-C6-10 arylsilyl group such as a triphenylsilyl group.
Further, in these "substituents", any hydrogen atom in the substituent may be substituted with a group having a different structure.
　また、上記の「３～６員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環の構成原子（環員原子ということがある。）として含む３～６員の環式化合物、すなわち「３～６員環のヘテロシクリル化合物」の任意の環原子から一個の水素原子を除去することにより生成される基である。
　上記の「３～６員環のヘテロシクリル基」とは、「窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環員原子として含む３～６員環のヘテロシクリル基」とも表現できる。
　ヘテロシクリル基は、単環および多環のいずれであってもよい。多環ヘテロシクリル基は、少なくとも一つの環がヘテロ環であれば、残りの環が飽和脂環、不飽和脂環または芳香環のいずれであってもよい。「３～６員環のヘテロシクリル基」としては、３～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。 Further, the above-mentioned "heterocyclyl group having a 3- to 6-membered ring" means that 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom are constituent atoms of the ring (referred to as ring-membered atoms). It is a group produced by removing one hydrogen atom from any ring atom of a 3- to 6-membered cyclic compound, that is, a "3- to 6-membered heterocyclyl compound" contained as (is).
The above-mentioned "3- to 6-membered ring heterocyclyl group" is a 3- to 6-membered ring heterocyclyl containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring-membered atoms. It can also be expressed as "base".
The heterocyclyl group may be monocyclic or polycyclic. The polycyclic heterocyclyl group may be any of a saturated alicyclic, an unsaturated alicyclic or an aromatic ring as long as at least one ring is a heterocycle. Examples of the "3- to 6-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group. ..
　３～６員環の飽和ヘテロシクリル基としては、アジリジニル基、エポキシ基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。 Examples of the saturated heterocyclyl group having a 3- to 6-membered ring include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group and a dioxanyl group.
　５員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
　６員環のヘテロアリール基としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。 Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be mentioned.
Examples of the 6-membered ring heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
〔Ａｒ〕
　式（I）中、Ａｒは、置換若しくは無置換のＣ６～１０アリール基または置換若しくは無置換の５～６員環のヘテロアリール基を示す。
　Ａｒにおける「Ｃ６～１０アリール基」は、単環若しくは多環の芳香族炭化水素の環上の水素が一つ抜けて形成される基である。Ｃ６～１０アリール基としては、フェニル基、ナフチル基などを挙げることができ、好ましくはフェニル基を挙げることができる。 [Ar]
In formula (I), Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered ring heteroaryl group.
The "C6 to 10 aryl group" in Ar is a group formed by removing one hydrogen on the ring of a monocyclic or polycyclic aromatic hydrocarbon. Examples of the C6 to 10 aryl group include a phenyl group and a naphthyl group, and preferably a phenyl group.
　Ａｒの「５～６員環のヘテロアリール基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環の構成原子（環員原子ということがある。）として含む５～６員の環式芳香族化合物、すなわち「５～６員環のヘテロアリール化合物」の任意の環原子から一個の水素原子を除去することにより生成される基である。
　上記の「５～６員環のヘテロアリール基」とは、「窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環員原子として含む５～６員環のヘテロアリール基」とも表現できる。
　５員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
　６員環のヘテロアリール基としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
　これらの中でも、ピラゾリル基、ピリジル基、またはピリダジニル基が好ましい。 The "5- to 6-membered heteroaryl group" of Ar means that 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom are constituent atoms of the ring (ring member atom). It is a group produced by removing one hydrogen atom from any ring atom of a 5- to 6-membered cyclic aromatic compound contained as (.), That is, a "5- to 6-membered heteroaryl compound".
The above-mentioned "5-6-membered heteroaryl group" refers to "a 5- to 6-membered ring containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms" as ring-membered atoms. It can also be expressed as a "heteroaryl group".
Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be mentioned.
Examples of the 6-membered ring heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
Among these, a pyrazolyl group, a pyridyl group, or a pyridazinyl group is preferable.
　Ａｒにおける、「Ｃ６～１０アリール基」または「５～６員環のヘテロアリール基」上の置換基（Ｘ3と言うことがある。）としては、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、ホルミル基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換の５～６員環のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換の５～６員環のヘテロアリールオキシ基、ＲaＲbＮ－ＣＯ－で表される基、ＲcＣＯＮＲd－で表される基、ＲcＯＮ=Ｃ(Ｒd)－で表される基、水酸基、ニトロ基、またはシアノ基を挙げることができる。 In Ar, (sometimes referred to as X 3.) "C6 ~ 10 aryl group" or a substituent on "5- to 6-membered heteroaryl group ring" As the halogeno group, a substituted or unsubstituted C1 ~ 6 Alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, formyl groups , Substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or Unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-8 cycloalkyl groups, substituted or unsubstituted C6-10aryl groups, substituted or unsubstituted 5-6-membered ring heteroaryl groups, substituted or An unsubstituted C6 to 10 aryloxy group, a substituted or unsubstituted 5- to 6-membered ring heteroaryloxy group, a group represented by R a R b N-CO-, and a group represented by R c CONR d-. , R c ON = C (R d )-, a group represented by a hydroxyl group, a nitro group, or a cyano group can be mentioned.
　Ｘ3の一つである「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the "halogeno group" which is one of X 3 include a fluoro group, a chloro group, a bromo group, an iod group and the like.
　Ｘ3の一つである「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。アルキル基としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などを挙げることができる。 The "C1 to 6 alkyl group" which is one of X 3 may be a straight chain or a branched chain. Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. , I-Pentyl group, Neopentyl group, 2-Methylbutyl group, 2,2-dimethylpropyl group, i-Hexyl group and the like.
　Ｘ3の一つである「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 "C2-6 alkenyl group" which is one of X 3 includes vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group and 1-methyl-2. -Propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group , 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
　Ｘ3の一つである「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 "C2-6 alkynyl group" which is one of X 3 includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group and 1-methyl-2. -Propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group , 1-Hexynyl group, 1,1-dimethyl-2-butynyl group and the like.
　Ｘ3の一つである「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、ｉ－プロポキシ基、ｉ－ブトキシ基、ｓ－ブトキシ基、ｔ－ブトキシ基、ｉ－ヘキシルオキシ基などを挙げることができる。 Examples of the "C1 to 6 alkoxy group" which is one of X 3 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, and an i-propoxy group. Examples thereof include an i-butoxy group, an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
　Ｘ3の一つである「Ｃ２～６アルケニルオキシ基」としては、ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などを挙げることができる。 Examples of the "C2 to 6 alkenyloxy group" which is one of X 3 include a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group and the like.
　Ｘ3の一つである「Ｃ１～６アルキルカルボニル基」としては、アセチル基、プロピオニル基などを挙げることができる。 Examples of the "C1 to 6 alkylcarbonyl group" which is one of X 3 include an acetyl group and a propionyl group.
　Ｘ3の一つである「Ｃ１～６アルコキシカルボニル基」としては、メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 Examples of the “C1 to 6 alkoxycarbonyl group” which is one of X 3 include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
　Ｘ3の一つである「Ｃ１～６アルキルチオ基」は、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。 "C1-6 alkylthio group" which is one of X 3 includes methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like. Can be done.
　Ｘ3の一つである「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。 Examples of the "C1 to 6 alkylsulfinyl group" which is one of X 3 include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
　Ｘ3の一つである「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 Examples of the "C1 to 6 alkylsulfonyl group" which is one of X 3 include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
　Ｘ3である「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ２～６アルケニルオキシ基」、「Ｃ１～６アルキルカルボニル基」、「Ｃ１～６アルコキシカルボニル基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、または「Ｃ１～６アルキルスルホニル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　フェニル基、ナフチル基などのＣ６～１０アリール基；　シアノ基；　を挙げることができる。 X 3 "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C1-6 alkyl" As a substituent on the "carbonyl group", "C1-6 alkoxycarbonyl group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group", preferably a fluorogroup, Halogeno groups such as chloro group, bromo group, iodo group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like. C1-6 alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group, naphthyl group; cyano Group; can be mentioned.
　「Ｃ６～１０アリール基」または「５～６員環のヘテロアリール基」上の置換基の一つである「Ｃ３～８シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基などを挙げることができる。 Examples of the "C3-8 cycloalkyl group" which is one of the substituents on the "C6 to 10 aryl group" or the "5- to 6-membered heteroaryl group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl. Groups, cycloheptyl groups and the like can be mentioned.
　Ｘ3の一つである「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基などを挙げることができる。 Examples of the "C6 to 10 aryl group" which is one of X 3 include a phenyl group and a naphthyl group.
　Ｘ3の一つである「５～６員環のヘテロアリール基」としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；などを挙げることができる。 Which is one of X 3 as "heteroaryl group having 5 to 6-membered ring" include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, a triazolyl group , Oxaziazolyl group, thiadiazolyl group, tetrazolyl group and other 5-membered heteroaryl groups; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group and other 6-membered heteroaryl groups; and the like.
　Ｘ3の一つである「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the "C6 to 10 aryloxy group" which is one of X 3 include a phenoxy group and a naphthoxy group.
　Ｘ3の一つである「５～６員環のヘテロアリールオキシ基」としては、チアゾリルオキシ基、ピリジルオキシ基などの５～６員環のヘテロアリールオキシ基を挙げることができる。 Examples of the "5- to 6-membered heteroaryloxy group" which is one of X 3 include a 5- to 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group.
　Ｘ3である「Ｃ３～８シクロアルキル基」、「Ｃ６～１０アリール基」、「５～６員環のヘテロアリール基」、「Ｃ６～１０アリールオキシ基」、または「５～６員環のヘテロアリールオキシ基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　シアノ基；などを挙げることができる。 X 3 "C3-8 cycloalkyl group", "C6-10 aryl group", "5-6-membered heteroaryl group", "C6-10 aryloxy group", or "5-6-membered ring" As the substituent on the "heteroaryloxy group", preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, C1-6 alkyl groups such as s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro- C1-6 haloalkyl groups such as n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, C1-6 alkoxy groups such as s-butoxy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group Group; cyano group; and the like.
　Ｘ3の一つである「ＲaＲbＮ－ＣＯ－で表される基」において、Ｒaは、水素原子、Ｃ１～６アルキル基またはＣ１～６アルコキシ基を示し、Ｒbは、水素原子またはＣ１～６アルキル基を示し、ＲaとＲbは一緒になって、Ｃ３～６アルキレン基を形成してもよい。 In "Group represented by R a R b N-CO-" which is one of X 3 , R a represents a hydrogen atom, a C1 to 6 alkyl group or a C1 to 6 alkoxy group, and R b is hydrogen. It may represent an atom or a C1-6 alkyl group and R a and R b may be combined to form a C3-6 alkylene group.
　ＲaおよびＲbにおける「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などを挙げることができる。 The "C1-6 alkyl groups" in Ra and R b include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group and i-butyl. Groups, s-butyl groups, t-butyl groups, i-pentyl groups, neopentyl groups, 2-methylbutyl groups, 2,2-dimethylpropyl groups, i-hexyl groups and the like can be mentioned.
　「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などを挙げることができる。 Examples of the "C1 to 6 alkoxy group" include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group and the like. can.
　ＲaとＲbが一緒になって形成する「Ｃ３～６アルキレン基」としては、トリメチレン基、テトラメチレン基、ペンタメチレン基などが挙げられる。 Examples of the "C3 to 6 alkylene group" formed by Ra and R b together include a trimethylene group, a tetramethylene group, and a pentamethylene group.
　ＲaＲbＮ－ＣＯ－で表される基としては、カルバモイル基、Ｎ－メチルアミノカルボニル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－エチル－Ｎ－メチルアミノカルボニル基、Ｎ－メトキシ－Ｎ－メチルアミノカルボニル基、ピロリジン－１－カルボニル基などを挙げることができる。 Examples of the group represented by R a R b N-CO- include a carbamoyl group, an N-methylaminocarbonyl group, an N, N-dimethylaminocarbonyl group, an N-ethyl-N-methylaminocarbonyl group, and an N-methoxy-. Examples thereof include an N-methylaminocarbonyl group and a pyrrolidine-1-carbonyl group.
　Ｘ3の一つである「ＲcＣＯＮＲd－で表される基」において、Ｒcは、Ｃ１～６アルキル基を示し、Ｒdは、水素原子またはＣ１～６アルキル基を示す。
　ＲcおよびＲdにおける「Ｃ１～６アルキル基」としては、ＲaおよびＲbにおいて具体的に例示したそれらと同じものを挙げることができる。
　ＲcＣＯＮＲd－で表される基としては、アセタミド基、Ｎ－メチルアセタミド基などを挙げることができる。 In "group represented by R c CONR d- " which is one of X 3 , R c represents a C1 to 6 alkyl group, and R d represents a hydrogen atom or a C1 to 6 alkyl group.
Examples of the “C1 to 6 alkyl groups” in R c and R d include the same as those specifically exemplified in R a and R b.
Examples of the group represented by R c CONR d − include an acetamide group and an N-methylacetamide group.
　Ｘ3の一つである「ＲcＯＮ=Ｃ(Ｒd)－で表される基」において、Ｒcは、Ｃ１～６アルキル基を示す。Ｒdは、水素原子またはＣ１～６アルキル基を示し、好ましくは水素原子を示す。
　ＲcおよびＲdにおける「Ｃ１～６アルキル基」としては、ＲaおよびＲbにおいて具体的に例示したそれらと同じものを挙げることができる。 In "group represented by R c ON = C (R d )-" which is one of X 3 , R c represents a C1 to 6 alkyl group. R d represents a hydrogen atom or a C1-6 alkyl group, preferably a hydrogen atom.
Examples of the “C1 to 6 alkyl groups” in R c and R d include the same as those specifically exemplified in R a and R b.
　これらの中でも、Ａｒにおける、「Ｃ６～１０アリール基」または「５～６員環のヘテロアリール基」上の置換基としては、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基（より好ましくはハロゲノ基で置換されていてもよいＣ１～６アルキル基）、置換若しくは無置換のＣ１～６アルコキシ基（より好ましくは、ハロゲノ基で置換されていてもよいＣ１～６アルコキシ基）、置換若しくは無置換のＣ１～６アルキルチオ基(より好ましくはハロゲノ基で置換されていてもよいＣ１～６アルキルチオ基)、ＲcＯＮ=Ｃ(Ｒd)－で表される基、またはシアノ基が好ましく、ハロゲノ基、ハロゲノ基で置換されていもよいＣ１～６アルキル基、ハロゲノ基で置換されていもよいＣ１～６アルコキシ基、または、ＲcＯＮ=Ｃ(Ｒd)－で表される基がより好ましく挙げられる。 Among these, as the substituent on the "C6 to 10 aryl group" or "5- to 6-membered ring heteroaryl group" in Ar, a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group (more preferably). C1-6 alkyl groups optionally substituted with a halogeno group), substituted or unsubstituted C1-6 alkoxy groups (more preferably C1-6 alkoxy groups optionally substituted with a halogeno group), substituted or absent. Substituted C1-6 alkylthio groups (more preferably C1-6 alkylthio groups optionally substituted with a halogeno group), groups represented by R c ON = C (R d )-, or cyano groups are preferred, and halogeno. More preferably, a group, a C1 to 6 alkyl group optionally substituted with a halogeno group, a C1 to 6 alkoxy group optionally substituted with a halogeno group, or a group represented by R c ON = C (R d )-is more preferable. Can be mentioned.
〔Ｒ1、Ｒ2、Ｒ3、Ｒ4〕
　式（I）中のＲ1は、シアノ基または置換若しくは無置換のチオカルバモイル基を示す。
　式（I）中のＲ2は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示す。
　式（I）中のＲ3は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示す。
　式（I）中のＲ4は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示す。 [R 1 , R 2 , R 3 , R 4 ]
R 1 in formula (I) represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
R 2 in formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
R 3 in formula (I) represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
R 4 in formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
　Ｒ1における「置換のチオカルバモイル基」としては、メチルチオカルバモイル基、ジメチルチオカルバモイル基、エチル（メチル）チオカルバモイル基などのモノまたはジＣ１～６アルキル置換チオカルバモイル基を挙げることができる。 Examples of the "substituted thiocarbamoyl group" in R 1 include mono or di-C1-6 alkyl-substituted thiocarbamoyl groups such as methylthiocarbamoyl group, dimethylthiocarbamoyl group and ethyl (methyl) thiocarbamoyl group.
　Ｒ2、Ｒ3およびＲ4における「ハロゲノ基」、「置換若しくは無置換のＣ１～６アルキル基」、および「置換若しくは無置換のＣ１～６アルコキシ基」としては、Ａｒにおいて具体的に例示したそれらと同じものを挙げることができる。 The "halogeno group", "substituted or unsubstituted C1-6 alkyl group", and "substituted or unsubstituted C1-6 alkoxy group" in R 2 , R 3 and R 4 are specifically exemplified in Ar. The same ones can be mentioned.
　式（I）中のＲ1は、シアノ基または無置換のチオカルバモイル基であることが好ましい。
　式（I）中のＲ2は、水素原子であることが好ましい。
　式（I）中のＲ3は、ハロゲノ基；ハロゲノ基もしくはＣ１～６アルコキシ基で置換されていてもよいＣ１～６アルキル基；無置換のＣ１～６アルコキシ基；またはシアノ基であることが好ましい。
　式（I）中のＲ4は、水素原子であることが好ましい。 R 1 in formula (I) is preferably a cyano group or an unsubstituted thiocarbamoyl group.
R 2 in the formula (I) is preferably a hydrogen atom.
R 3 in formula (I) may be a halogeno group; a C1-6 alkyl group optionally substituted with a halogeno group or a C1-6 alkoxy group; an unsubstituted C1-6 alkoxy group; or a cyano group. preferable.
R 4 in the formula (I) is preferably a hydrogen atom.
〔Ｑ〕
　Ｑは、式（Qa）または式（Qb）で表わされる基を示す。 [Q]
Q indicates a group represented by the formula (Qa) or the formula (Qb).
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
〔式(Qa)〕
　式(Qa)中、矢印は結合位置を示す。
　式(Qa)中、ｐ1は、括弧内のメチレンの数を示し且つ０または１、好ましくは１であり、ｐ2は、括弧内のメチレンの数を示し且つ０～２のいずれかの整数であり、好ましくは１である。 [Equation (Qa)]
In equation (Qa), the arrow indicates the bond position.
In formula (Qa), p 1 indicates the number of methylene in parentheses and is 0 or 1, preferably 1, and p 2 indicates the number of methylene in parentheses and is an integer of 0-2. It is preferably 1.
　式(Qa)で表わされる基は、ｐ1が１であり且つＰ2が１であるとき、式（Qa-1）で表わされる。 The group represented by the formula (Qa) is represented by the formula (Qa-1) when p 1 is 1 and P 2 is 1.
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
　式(Qa)または（Qa-1）中、Ｘ1は、環上の置換基を示し、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、置換若しくは無置換のＣ１～６アルキルスルホニルオキシ基、または置換若しくは無置換のＣ１～６アルキルチオ基であり、ｍは、Ｘ1の数を示し且つ化学的の許容される０～４のいずれかの整数（好ましくは０）であり、Ｘ2は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示す。 In formula (Qa) or (Qa-1), X 1 represents a substituent on the ring, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyl. an oxy group, or a substituted or unsubstituted C1 ~ 6 alkylthio group,, m is any integer number and chemically permissible 0 indicates the X 1 4 (preferably 0), X Reference numeral 2 is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1 to 6 alkoxy group.
　Ｘ1における「ハロゲノ基」、「置換若しくは無置換のＣ１～６アルキル基」、および「置換若しくは無置換のＣ１～６アルキルチオ基」としては、Ａｒにおいて具体的に例示したそれらと同じものを挙げることができる。 Examples of the "halogeno group", "substituted or unsubstituted C1 to 6 alkyl groups", and "substituted or unsubstituted C1 to 6 alkylthio groups" in X 1 are the same as those specifically exemplified in Ar. be able to.
　Ｘ1における「Ｃ１～６アルキルスルホニルオキシ基」としては、メチルスルホニルオキシ基、エチルスルホニルオキシ基、ｔ－ブチルスルホニルオキシ基などを挙げることができる。
　「Ｃ１～６アルキルスルホニルオキシ基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基を挙げることができる。 Examples of the "C1 to 6 alkylsulfonyloxy group" in X 1 include a methylsulfonyloxy group, an ethylsulfonyloxy group, and a t-butylsulfonyloxy group.
As the substituent on the "C1 to 6 alkylsulfonyloxy group", a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.
　Ｘ2における「ハロゲノ基」、「置換若しくは無置換のＣ１～６アルキル基」、および「置換若しくは無置換のＣ１～６アルコキシ基」としては、Ａｒにおいて具体的に例示したそれらと同じものを挙げることができる。
　Ｘ2は、好ましくは、水素原子、ハロゲノ基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示し、より好ましくは、水素原子、水酸基、または無置換のＣ１～６アルコキシ基を示す。 Examples of the "halogeno group", "substituted or unsubstituted C1-6 alkyl group", and "substituted or unsubstituted C1-6 alkoxy group" in X 2 are the same as those specifically exemplified in Ar. be able to.
X 2 preferably represents a hydrogen atom, a halogeno group, a hydroxyl group, or a substituted or unsubstituted C1 to 6 alkoxy group, and more preferably a hydrogen atom, a hydroxyl group, or an unsubstituted C1 to 6 alkoxy group.
　式(Qa)または（Qa-1）中、Ｙは、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロアリール基を示す。 In formula (Qa) or (Qa-1), Y is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring hetero. Indicates an aryl group.
（１）Ｙにおける「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。アルキル基としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などを挙げることができる。 (1) The "C1 to 6 alkyl group" in Y may be a straight chain or a branched chain. Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. , I-Pentyl group, Neopentyl group, 2-Methylbutyl group, 2,2-Dimethylpropyl group, i-Hexyl group and the like.
　Ｙにおける「Ｃ１～６アルキル基」上の好ましい置換基としては、ハロゲノ基、水酸基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、Ｃ１～６ハロアルキルチオ基、Ｃ１～６ハロアルキルスルフィニル基、Ｃ１～６ハロアルキルスルホニル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換の５～６員環のヘテロアリール基、置換若しくは無置換の５～６員環のヘテロアリールオキシ基、Ｃ１～６アルキルカルボニル基、Ｃ１～６アルコキシカルボニル基、ＲaＲbＮ－で表される基、ＲaＲbＮ－ＣＯ－で表される基、ＲaＲbＮ－ＳＯ2－で表される基、ＲcＣＯＮＲd－で表される基、ＲcＳＯ2ＮＲd－で表される基、ＲeＯ－Ｎ＝ＣＲf－で表される基、またはシアノ基である。 Preferred substituents on the "C1-6 alkyl group" in Y include a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, and a C1-6 alkyl group. 6 Alkylsulfonyl groups, C1-6 haloalkylthio groups, C1-6 haloalkylsulfinyl groups, C1-6 haloalkylsulfonyl groups, substituted or unsubstituted C6-10aryl groups, substituted or unsubstituted C6-10aryloxy groups, substituted Alternatively, an unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a C1 to 6 alkylcarbonyl group, a C1 to 6 alkoxycarbonyl group, R a R b N- Group represented by, group represented by R a R b N-CO-, group represented by R a R b N-SO 2- , group represented by R c CONR d- , group represented by R c SO 2 A group represented by NR d −, a group represented by R e ON = CR f −, or a cyano group.
　具体的には、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　水酸基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基；　メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；　メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；　トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基；　トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；　トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；　フェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基などのハロ置換、トリフルオロメチル置換、若しくは無置換のＣ６～１０アリール基；　フェニルオキシ基、４－クロロフェニルオキシ基、４－トリフルオロメチルフェニルオキシ基などのハロ置換、トリフルオロメチル置換、若しくは無置換のＣ６～１０アリールオキシ基；　ハロ置換、Ｃ１～６アルキル置換、トリフルオロメチル置換、若しくは無置換の５～６員環のヘテロアリール基（好ましくは、オキサジアゾリル基）；　ハロ置換、Ｃ１～６アルキル置換、トリフルオロメチル置換、若しくは無置換の５～６員環のヘテロアリールオキシ基（好ましくは、ピリジルオキシ基）；　アセチル基、プロピオニル基などのＣ１～６アルキルカルボニル基；　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基；　シアノ基を挙げることができる。 Specifically, halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i. -C1-6 alkoxy groups such as butoxy group and t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; methylthio group and ethylthio C1 to 6 alkylthio groups such as groups; C1 to 6 alkylsulfinyl groups such as methylsulfinyl group and ethylsulfinyl group; C1 to 6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; trifluoromethylthio group, 2,2 C1-6 haloalkylthio groups such as 2-trifluoroethylthio group; C1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group, 2, C1-6 haloalkylsulfonyl groups such as 2,2-trifluoroethylsulfonyl group; halo-substituted, trifluoromethyl-substituted, or unsubstituted C6-10 of phenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, etc. Aryl group; halo-substituted, trifluoromethyl-substituted, or unsubstituted C6-10 aryloxy groups such as phenyloxy group, 4-chlorophenyloxy group, 4-trifluoromethylphenyloxy group; halo-substituted, C1-6 alkyl-substituted , Trifluoromethyl-substituted, or unsubstituted 5- to 6-membered ring heteroaryl group (preferably oxadiazolyl group); halo-substituted, C1 to 6-alkyl substituted, trifluoromethyl-substituted, or unsubstituted 5- to 6-membered ring. Heteroaryloxy group (preferably pyridyloxy group); C1 to 6 alkylcarbonyl groups such as acetyl group and propionyl group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, t- C1 to 6 alkoxycarbonyl groups such as butoxycarbonyl groups; cyano groups can be mentioned.
　「Ｃ１～６アルキル基」上の好ましい置換基の一つである「ＲaＲbＮ－で表される基」において、Ｒaは、水素原子、Ｃ１～６アルキル基またはＣ１～６アルコキシ基を示し、Ｒbは、水素原子またはＣ１～６アルキル基を示し、ＲaとＲbは一緒になって、Ｃ３～６アルキレン基を形成してもよい。 In the "group represented by R a R b N-" which is one of the preferable substituents on the "C1 to 6 alkyl group" , Ra is a hydrogen atom, a C1 to 6 alkyl group or a C1 to 6 alkoxy group. , R b represents a hydrogen atom or a C1-6 alkyl group, and R a and R b may be combined to form a C3-6 alkylene group.
　ＲaおよびＲbにおける「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などを挙げることができる。 The "C1-6 alkyl groups" in Ra and R b include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group and i-butyl. Groups, s-butyl groups, t-butyl groups, i-pentyl groups, neopentyl groups, 2-methylbutyl groups, 2,2-dimethylpropyl groups, i-hexyl groups and the like can be mentioned.
　「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などを挙げることができる。 Examples of the "C1 to 6 alkoxy group" include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, a t-butoxy group and the like. can.
　ＲaとＲbが一緒になって形成する「Ｃ３～６アルキレン基」としては、トリメチレン基、テトラメチレン基、ペンタメチレン基などが挙げられる。 Examples of the "C3 to 6 alkylene group" formed by Ra and R b together include a trimethylene group, a tetramethylene group, and a pentamethylene group.
　ＲaＲbＮ－で表される基としては、アミノ基、Ｎ－メチルアミノ基、Ｎ，Ｎ－ジメチルアミノ基、Ｎ－エチル－Ｎ－メチルアミノ基、Ｎ－メトキシ－Ｎ－メチルアミノ基、ピロリジン－１－イル基などを挙げることができる。 Examples of the group represented by R a R b N- include an amino group, an N-methylamino group, an N, N-dimethylamino group, an N-ethyl-N-methylamino group, and an N-methoxy-N-methylamino group. , Pyrrolidine-1-yl group and the like.
　「Ｃ１～６アルキル基」上の好ましい置換基の一つである「ＲaＲbＮ－ＣＯ－で表される基」において、ＲaおよびＲbは、上記と同様の意味を示す。
　ＲaＲbＮ－ＣＯ－で表される基としては、カルバモイル基、Ｎ－メチルアミノカルボニル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－エチル－Ｎ－メチルアミノカルボニル基、Ｎ－メトキシ－Ｎ－メチルアミノカルボニル基、ピロリジン－１－カルボニル基などを挙げることができる。 In "group represented by R a R b N-CO-" which is one of the preferable substituents on "C1 to 6 alkyl groups" , R a and R b have the same meanings as described above.
Examples of the group represented by R a R b N-CO- include a carbamoyl group, an N-methylaminocarbonyl group, an N, N-dimethylaminocarbonyl group, an N-ethyl-N-methylaminocarbonyl group, and an N-methoxy-. Examples thereof include an N-methylaminocarbonyl group and a pyrrolidine-1-carbonyl group.
　「Ｃ１～６アルキル基」上の好ましい置換基の一つである「ＲaＲbＮ－ＳＯ2－で表される基」において、ＲaおよびＲbは、上記と同様の意味を示す。
　ＲaＲbＮ－ＳＯ2－で表される基としては、スルファモイル基、Ｎ－メチルアミノスルホニル基、Ｎ，Ｎ－ジメチルアミノスルホニル基、Ｎ－エチル－Ｎ－メチルアミノスルホニル基、Ｎ－メトキシ－Ｎ－メチルアミノスルホニル基、ピロリジン－１－イルスルホニル基などを挙げることができる。 In "group represented by R a R b N-SO 2- " which is one of the preferable substituents on "C1 to 6 alkyl groups" , R a and R b have the same meanings as described above.
The groups represented by R a R b N-SO 2- are sulfamoyl group, N-methylaminosulfonyl group, N, N-dimethylaminosulfonyl group, N-ethyl-N-methylaminosulfonyl group, N-methoxy. -N-Methylaminosulfonyl group, pyrrolidine-1-ylsulfonyl group and the like can be mentioned.
　「Ｃ１～６アルキル基」上の好ましい置換基の一つである「ＲcＣＯＮＲd－で表される基」において、Ｒcは、Ｃ１～６アルキル基を示し、Ｒdは、水素原子またはＣ１～６アルキル基を示す。
　ＲcおよびＲdにおける「Ｃ１～６アルキル基」としては、ＲaおよびＲbにおいて具体的に例示したそれらと同じものを挙げることができる。
　ＲcＣＯＮＲd－で表される基としては、アセタミド基、Ｎ－メチルアセタミド基などを挙げることができる。 In the "group represented by R c CONR d- " which is one of the preferred substituents on the "C1-6 alkyl group" , R c represents a C1-6 alkyl group and R d is a hydrogen atom or It shows a C1-6 alkyl group.
Examples of the “C1 to 6 alkyl groups” in R c and R d include the same as those specifically exemplified in R a and R b.
Examples of the group represented by R c CONR d − include an acetamide group and an N-methylacetamide group.
　「Ｃ１～６アルキル基」上の好ましい置換基の一つである「ＲcＳＯ2ＮＲd－で表される基」おいて、ＲcおよびＲdは、上記と同様の意味を示す。
　ＲcＳＯ2ＮＲd－で表される基としては、メチルスルホンアミド基、Ｎ－メチルメチルスルホンアミド基などを挙げることができる。 In "group represented by R c SO 2 NR d- " which is one of the preferable substituents on "C1 to 6 alkyl groups" , R c and R d have the same meanings as described above.
Examples of the group represented by R c SO 2 NR d − include a methyl sulfonamide group and an N-methyl methyl sulfonamide group.
　「Ｃ１～６アルキル基」上の好ましい置換基の一つである「ＲeＯ－Ｎ＝ＣＲf－で表される基」において、Ｒeは、Ｃ１～６アルキル基を示し、Ｒfは、水素原子またはＣ１～６アルキル基を示す。
　ＲeおよびＲfにおける「Ｃ１～６アルキル基」としては、ＲaおよびＲbにおいて具体的に例示したそれらと同じものを挙げることができる。
　ＲeＯ－Ｎ＝ＣＲf－で表される基としては、（メトキシイミノ）メチル基、（エトキシイミノ）メチル基、（メトキシイミノ）エチル基、（エトキシイミノ）エチル基などを挙げることができる。 In the "group represented by R e ON = CR f- " which is one of the preferable substituents on the "C1 to 6 alkyl group" , R e indicates a C1 to 6 alkyl group, and R f is , Hydrogen atom or C1-6 alkyl group.
Examples of the "C1 to 6 alkyl groups" in R e and R f include the same as those specifically exemplified in R a and R b.
R e O-N = CR f - The group represented by, (methoxyimino) methyl group, (ethoxyimino) methyl group, (methoxyimino) ethyl group, and the like (ethoxyimino) ethyl ..
　これらの中でも、Ｙにおける「Ｃ１～６アルキル基」上のより好ましい置換基としては、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルフィニル基、Ｃ１～６アルキルスルホニル基、またはＲaＲbＮ－ＣＯ－で表される基（好ましくはＮ－メチルアミノカルボニル基）を挙げることができる。 Among these, the "C1 ~ 6 alkyl group" Ueno more preferred substituents on Y, C1 ~ 6 alkylthio group, C1 ~ 6 alkylsulfinyl group, C1 ~ 6 alkylsulfonyl group or a R a R b N-CO, A group represented by − (preferably an N-methylaminocarbonyl group) can be mentioned.
（２）Ｙにおける「Ｃ６～１０アリール基」は、単環若しくは多環の芳香族炭化水素の環上の水素が一つ抜けて形成される基である。Ｃ６～１０アリール基としては、フェニル基、ナフチル基などを挙げることができ、好ましくはフェニル基を挙げることができる。 (2) The "C6 to 10 aryl group" in Y is a group formed by removing one hydrogen on the ring of a monocyclic or polycyclic aromatic hydrocarbon. Examples of the C6 to 10 aryl group include a phenyl group and a naphthyl group, and preferably a phenyl group.
　Ｃ６～１０アリール基上の置換基としては、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、ホルミル基、置換若しくは無置換のＣ１～６アルキルカルボニル基、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～８シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換の５～６員環のヘテロアリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換の５～６員環のヘテロアリールオキシ基、水酸基、ニトロ基、またはシアノ基を挙げることができる。
　これらの具体例は、Ａｒにおいて例示したものと同じものを挙げることができる。 Substituents on the C6-10 aryl group include a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted group. Unsubstituted C1-6 alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, formyl groups, substituted or unsubstituted C1-6 alkylcarbonyl groups, substituted or unsubstituted C1-6 alkoxycarbonyl groups, substituted or Unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-8 cycloalkyl groups, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 5- to 6-membered heteroaryl group, substituted or unsubstituted C6 to 10 aryloxy group, substituted or unsubstituted 5- to 6-membered ring heteroaryloxy group, hydroxyl group , Nitro group, or cyano group.
Specific examples of these can be the same as those exemplified in Ar.
（３）Ｙにおける「５～６員環のヘテロアリール基」は、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環の構成原子（環員原子ということがある。）として含む５～６員の環式芳香族化合物、すなわち「５～６員環のヘテロアリール化合物」の任意の環原子から一個の水素原子を除去することにより生成される基である。
　上記の「５～６員環のヘテロアリール基」とは、「窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環員原子として含む５～６員環のヘテロアリール基」とも表現できる。
　５員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
　６員環のヘテロアリール基としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
　５～６員環のヘテロアリール基上の置換基としては、（２）で説明したＣ６～１０アリール基上の置換基と同様のものを挙げることができ、Ｃ１～６アルキル基またはハロゲノ基を好ましく挙げることができる。 (3) The "5- to 6-membered heteroaryl group" in Y means that 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom are constituent atoms of the ring (ring member atom). Is a group produced by removing one hydrogen atom from any ring atom of a 5- to 6-membered cyclic aromatic compound, that is, a "5- to 6-membered heteroaryl compound". ..
The above-mentioned "5-6-membered heteroaryl group" refers to "a 5- to 6-membered ring containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms" as ring-membered atoms. It can also be expressed as a "heteroaryl group".
Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be mentioned.
Examples of the 6-membered ring heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
Examples of the substituent on the heteroaryl group of the 5- to 6-membered ring include the same substituents on the C6 to 10 aryl group described in (2), and a C1 to 6 alkyl group or a halogeno group can be used. It can be preferably mentioned.
　こららの中でも、Ｙは、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換の５～６員環のヘテロアリール基（好ましくは、トリアゾリル基、オキサジアゾリル基、または、ピリミジニル基）であることが好ましく、置換若しくは無置換のＣ１～６アルキル基、Ｃ１～６アルキル基で置換されていてもよい５員環のヘテロアリール基（好ましくは、トリアゾリル基もしくはオキサジアゾリル基）、または、ハロゲノ基で置換されていてもよい６員環のヘテロアリール基（好ましくはピリミジニル基）であることがより好ましい。 Among these, Y is a substituted or unsubstituted C1 to 6 alkyl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group (preferably a triazolyl group, an oxadiazolyl group, or a pyrimidinyl group). It is preferably a substituted or unsubstituted C1-6 alkyl group, a 5-membered heteroaryl group (preferably a triazolyl group or an oxadiazolyl group) which may be substituted with a C1-6 alkyl group, or a halogeno group. More preferably, it is a 6-membered heteroaryl group (preferably a pyrimidinyl group) which may be substituted with.
〔式(Qb)〕
　式(Qb)中、矢印は結合位置を示す。
　式(Qb)中、ｐ1は、括弧内のメチレンの数を示し且つ０または１、好ましくは１であり、ｐ2は、括弧内のメチレンの数を示し且つ０～２のいずれかの整数であり、好ましくは１である。 [Equation (Qb)]
In equation (Qb), the arrow indicates the bond position.
In formula (Qb), p 1 indicates the number of methylene in parentheses and is 0 or 1, preferably 1, and p 2 indicates the number of methylene in parentheses and is an integer of 0-2. It is preferably 1.
　式(Qb)で表わされる基は、ｐ1が１であり且つＰ2が１であるとき、式（Qb-1）で表わされる。 The group represented by the formula (Qb) is represented by the formula (Qb-1) when p 1 is 1 and P 2 is 1.
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　式(Qb)または（Qb-1）中、Ｘ1およびｍは、上記の式(Qa)中におけるＸ1と同じ意味を示す。 In the formula (Qb) or (Qb-1), X 1 and m have the same meaning as X 1 in the above formula (Qa).
　式(Qb)または（Qb-1）中、Ｙ’は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロアリール基を示す。 In formula (Qb) or (Qb-1), Y'is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, Alternatively, a substituted or unsubstituted 5- to 6-membered ring heteroaryl group is shown.
　Ｙ’における「置換若しくは無置換のＣ１～６アルキル基」、「置換若しくは無置換のＣ６～１０アリール基」、および「置換若しくは無置換の５～６員環のヘテロアリール基」としては、Ｙにおいて具体的に例示したそれらと同じものを挙げることができる。 The "substituted or unsubstituted C1 to 6 alkyl groups", "substituted or unsubstituted C6 to 10 aryl groups", and "substituted or unsubstituted 5- to 6-membered ring heteroaryl groups" in Y'are Y. The same ones as those specifically exemplified in the above can be mentioned.
　Ｙ’における「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。
　「Ｃ１～６アルキルスルホニル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；　フェニル基、ナフチル基などのＣ６～１０アリール基；　シアノ基；　を挙げることができる。 Examples of the "C1 to 6 alkylsulfonyl group" in Y'include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group and the like.
As the substituent on the "C1-6 alkylsulfonyl group", preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, n- C1-6 alkoxy groups such as butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1 ~ such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group 6 Haloalkoxy group; C6-10aryl group such as phenyl group and naphthyl group; cyano group;
　これらの中でも、Ｙ’は、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のフェニル基、または置換若しくは無置換の５～６員環のヘテロアリール基であることが好ましく、無置換のＣ１～６アルキルスルホニル基、ハロゲノ基で置換されていてもよいフェニル基、Ｃ１～６アルキル基で置換されていてもよい５員環のヘテロアリール基（好ましくはオキサジアゾリル基）、または、ハロゲノ基で置換されていてもよい６員環のヘテロアリール基（好ましくは、ピリジル基もしくはピリミジニル基）であることがより好ましい。 Among these, Y'preferably is a substituted or unsubstituted C1 to 6 alkylsulfonyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted 5- to 6-membered ring heteroaryl group, and is preferably absent. Substituted C1-6 alkylsulfonyl group, phenyl group optionally substituted with halogeno group, 5-membered heteroaryl group (preferably oxadiazolyl group) optionally substituted with C1-6 alkyl group, or halogenono More preferably, it is a 6-membered heteroaryl group (preferably a pyridyl group or a pyrimidinyl group) which may be substituted with a group.
　式（Ｉ）で表される化合物は、好ましくは、下記式（Ｉ－１）、（Ｉ－２）、もしくは（Ｉ－３）で表される。 The compound represented by the formula (I) is preferably represented by the following formula (I-1), (I-2), or (I-3).
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
　前記式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｙ、Ｙ’、Ｘ２およびＸ３は、前記の通りであり、ｎはフェニル基上の置換基Ｘ3の数を示し、１または２を示す。
　前記式（Ｉ－３）中、Ａｒ’は５～６員環のヘテロアリール基を示す。
　Ａｒ’における「５～６員環のヘテロアリール基」として、Ａｒにおける「５～６員環のヘテロアリール基」と同じものが挙げられ、好ましくは、ピラゾリル基、ピリジル基、またはピリダジニル基が挙げられる。 In the above formula, R 1 , R 2 , R 3 , R 4 , Y, Y', X 2 and X 3 are as described above, and n indicates the number of substituents X 3 on the phenyl group, and 1 Or 2 is shown.
In the formula (I-3), Ar'represents a heteroaryl group having a 5- to 6-membered ring.
Examples of the "5- to 6-membered heteroaryl group" in Ar'include the same as the "5- to 6-membered heteroaryl group" in Ar, preferably a pyrazolyl group, a pyridyl group, or a pyridazinyl group. Be done.
　化合物（I）の塩は、農園芸学的に許容される塩であれば、特に制限されない。例えば、塩酸、硫酸などの無機酸の塩；酢酸、乳酸などの有機酸の塩；リチウム、ナトリウム、カリウムなどのアルカリ金属の塩；カルシウム、マグネシウムなどのアルカリ土類金属の塩；鉄、銅などの遷移金属の塩；アンモニア、トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩などを挙げることができる。 The salt of compound (I) is not particularly limited as long as it is an horticulturally acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron, copper and the like. Transition metal salts; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, hydrazine and the like can be mentioned.
　化合物（I）または化合物（I）の塩は、その製造方法によって特に限定されない。また、化合物（I）の塩は、化合物（I）から公知の手法によって得ることができる。例えば、本発明の化合物（I）または化合物（I）の塩は、下記の製造方法、具体的には、実施例などに記載した公知の製造方法によって得ることができる。 The compound (I) or the salt of the compound (I) is not particularly limited depending on the production method thereof. Further, the salt of compound (I) can be obtained from compound (I) by a known method. For example, the compound (I) of the present invention or the salt of the compound (I) can be obtained by the following production method, specifically, a known production method described in Examples and the like.
（製造方法１）
　下記式（Ｉ－１ａ）で示される塩酸塩と、下記式（Ｉ－１ｂ）で示されるカルボン酸を、トリエチルアミンなどの適当な塩基の存在下で反応させ、下記式（Ｉ－１）で示される化合物を得る。下記式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｙ、Ｘ２、Ｘ３およびｎは、前記の通りである。 (Manufacturing method 1)
The hydrochloride represented by the following formula (I-1a) and the carboxylic acid represented by the following formula (I-1b) are reacted in the presence of an appropriate base such as triethylamine and represented by the following formula (I-1). To obtain the compound. In the following formula, R 1 , R 2 , R 3 , R 4 , Y, X 2 , X 3 and n are as described above.
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
　本発明のベンズアミド化合物（以下、「本発明化合物」と言うことがある。）は、植物の生育に影響する各種の農業害虫およびダニ類などの有害生物の防除効果に優れている。
　また、本発明化合物は、作物に対する薬害がなく、魚類や温血動物への毒性が低いため、安全性の高い化合物である。そのため、殺虫剤または殺ダニ剤の有効成分として有用である。 The benzamide compound of the present invention (hereinafter, may be referred to as "the compound of the present invention") is excellent in the effect of controlling various agricultural pests and pests such as mites that affect the growth of plants.
In addition, the compound of the present invention is a highly safe compound because it has no phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.
　さらに、近年、コナガ、ウンカ、ヨコバイ、アブラムシなど多くの害虫において各種既存薬剤に対する抵抗性が発達し、それら薬剤の効力不足問題を生じており、抵抗性系統の害虫にも有効な薬剤が望まれている。本発明化合物は、感受性系統のみならず、各種抵抗性系統の害虫や、さらに殺ダニ剤抵抗性系統のダニ類にも優れた防除効果を示す。 Furthermore, in recent years, resistance to various existing drugs has developed in many pests such as diamondback moth, planthopper, leafhopper, and aphid, causing a problem of insufficient efficacy of these drugs, and a drug effective against pests of resistant strains is desired. ing. The compound of the present invention exhibits an excellent control effect not only on sensitive strains but also on pests of various resistant strains and mites of acaricide-resistant strains.
　本発明化合物は、人獣に害を及ぼす外部寄生虫の防除効果に優れている。また、魚類や温血動物への毒性が低いため、安全性の高い化合物である。そのため、外部寄生虫の防除剤の有効成分として有用である。 The compound of the present invention is excellent in controlling ectoparasites that are harmful to humans and animals. In addition, it is a highly safe compound because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of a ectoparasite control agent.
　また、本発明化合物は、防除の対象となる生物のすべての発育ステージにおいて効力を示し、例えば、ダニ、昆虫などの卵、若虫、幼虫、蛹、成虫に対して優れた防除効果を示す。 In addition, the compound of the present invention is effective at all developmental stages of the organism to be controlled, and exhibits an excellent control effect on, for example, eggs such as mites and insects, larvae, larvae, pupae, and adults.
〔有害生物防除剤、殺虫若しくは殺ダニ剤〕
　本発明の有害生物防除剤、または殺虫若しくは殺ダニ剤は、本発明のベンズアミド化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の有害生物防除剤または殺虫若しくは殺ダニ剤に含まれる本発明化合物の量は有害生物の防除効果を示す限りにおいて特に制限されない。 [Pest control agents, insecticides or acaricides]
The pest control agent, or insecticide or acaricide of the present invention contains at least one selected from the benzamide compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent or the insecticide or acaricide of the present invention is not particularly limited as long as it shows the pest control effect.
　本発明の有害生物防除剤または殺虫若しくは殺ダニ剤は、穀物類；野菜類；根菜類；イモ類；花卉類；果樹類、観葉植物、茶、コーヒー、カカオなどの樹木類；牧草類；芝類；ワタなどの植物に対して用いることが好ましい。
　植物への施用において、本発明の有害生物防除剤または殺虫若しくは殺ダニ剤は、葉、茎、柄、花、蕾、果実、種子、スプラウト、根、塊茎、塊根、苗条、挿し木などのいずれの部位に用いてもよい。また、本発明の有害生物防除剤または殺虫若しくは殺ダニ剤は、施用される植物の種によって特に制限されない、植物の種としては、例えば、原種、変種、改良品種、栽培品種、突然変異体、ハイブリッド体、遺伝子組み換え体（ＧＭＯ）などが挙げられる。 The pest control agent or insecticide or acaricide of the present invention includes grains; vegetables; root vegetables; potatoes; flowers; fruit trees, foliage plants, tea, coffee, cacao and other trees; grasses; turf. Kind: Preferably used for plants such as cotton.
In application to plants, the pest control agent or insecticide or acaricide of the present invention includes any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, stalks, stalks, shoots, shoots, cuttings, etc. It may be used for the site. Further, the pest control agent or insecticide or acaricide of the present invention is not particularly limited depending on the species of the plant to which it is applied. Examples of the plant species include the original species, varieties, improved varieties, cultivars, mutants, etc. Examples include hybrids and genetically modified organisms (GMOs).
　本発明の有害生物防除剤は、各種の農業害虫およびダニ類を防除するために、種子処理、茎葉散布、土壌施用、水面施用などに使用することができる。 The pest control agent of the present invention can be used for seed treatment, foliage spraying, soil application, water surface application, etc. in order to control various agricultural pests and mites.
　本発明の有害生物防除剤によって防除可能な各種の農業害虫およびダニ類の具体例を以下に示す。 Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.
（１）鱗翅目（Lepidoptera）のチョウまたは蛾
　(a)ヒトリガ科（Arctiidae）のガ、例えば、アメリカシロヒトリ(Hyphantria cunea)、クワゴマダラヒトリ(Lemyra imparilis)；
　(b)チビガ科（Bucculatricidae）のガ、例えば、ナシチビガ(Bucculatrix pyrivorella)；
　(c)シンクイガ科（Carposinidae）のガ、例えば、モモシンクイガ(Carposina sasakii)；
　(d)ツトガ科（Crambidae）のガ、例えば、ジアファニア属種(Diaphania spp.)の、ワタヘリクロノメイガ(Diaphania indica)、アメリカウリノメイガ(Diaphania nitidalis)；例えば、オストリニア属種(Ostrinia spp.)の、アワノメイガ(Ostrinia furnacalis)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、アズキノメイガ(Ostrinia scapulalis)；その他、ニカメイガ(Chilo suppressalis)、コブノメイガ(Cnaphalocrocis medinalis)、モモノゴマダラノメイガ(Conogethes punctiferalis)、サウスウエスタンコーンボーラー(Diatraea grandiosella)、クワノメイガ(Glyphodes pyloalis)、ハイマダラノメイガ(Hellula undalis)、シバツトガ(Parapediasia teterrella)；
　(e)キバガ科（Gelechiidae）のガ、例えば、イモキバガ(Helcystogramma triannulella)、ワタアカミムシ(Pectinophora gossypiella)、ジャガイモキバガ(Phthorimaea operculella)、バクガ(Sitotroga cerealella)；
　(f)シャクガ科（Geometridae）のガ、例えば、ヨモギエダシャク(Ascotis selenaria)；
　(g)ホソガ科(Gracillariidae)のガ、例えば、チャノホソガ(Caloptilia theivora)、ミカンハモグリガ(Phyllocnistis citrella)、キンモンホソガ(Phyllonorycter ringoniella)；
　(h)セセリチョウ科（Hesperiidae）のチョウ、例えば、イチモンジセセリ(Parnara guttata)；
　(i)カレハガ科（Lasiocampidae）のガ、例えば、オビカレハ(Malacosoma neustria)；
　(j)ドクガ科（Lymantriidae）のガ、例えば、リマントリア属種(Lymantria spp.)の、マイマイガ(Lymantria dispar)、ノンネマイマイ(Lymantria monacha)；その他の、チャドクガ(Euproctis pseudoconspersa)、ヒメシロモンドクガ(Orgyia thyellina)； (1) Lepidoptera butterflies or moths (a) Arctiidae moths, such as the fall webworm (Hyphantria cunea) and the fall webworm (Lemyra imparilis);
(b) Bucculatricidae moths, such as Bucculatrix pyrivorella;
(c) Moths of the family Carposinidae, such as the peach moth (Carposina sasakii);
(d) Crambidae moths, such as the genus Diaphania spp., The genus Pyraustinae (Diaphania indica), the genus Pyraustinae (Diaphania nitidalis); , Awanomeiga (Ostrinia furnacalis), European cornballer (Ostrinia nubilalis), Azukinomeiga (Ostrinia scapulalis); Diatraea grandiosella), Kwanomeiga (Glyphodes pyloalis), Hellula undalis, Shibatuga (Parapediasia teterrella);
(e) Moths of the family Twirler moth (Gelechiidae), such as caterpillar (Helcystogramma triannulella), cotton bollworm (Pectinophora gossypiella), potato moth (Phthorimaea operculella), and angoumois grain moth (Sitotroga cerealella);
(f) Moths of the Geometridae family, such as Ascotis selenaria;
(g) Moths of the leaf miner moth (Gracillariidae), such as Chanohosoga (Caloptilia theivora), Satsuma mandarin (Phyllocnistis citrella), Phyllonorycter ringoniella;
(h) Skippers (Hesperiidae) butterflies, such as Parnara guttata;
(i) Lappet moth (Lasiocampidae) moths, such as Lackey moth (Malacosoma neustria);
(j) Lymantriidae moths, such as Lymantria spp., Lymantria dispar, Lymantria monacha; Others, Euproctis pseudoconspersa, Orgyia thyellina);
　(k)モグリガ科（Lyonetiidae ）のガ、例えば、リオネチア属種(Lyonetia spp.)の、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella malinella)；
　(l)ヤガ科（Noctuidae）のガ、例えば、スポドプテラ属種(Spodoptera spp.)の、スジキリヨトウ(Spodoptera depravata)、サザンアーミーワーム(Spodoptera eridania)、シロイチモジヨトウ(Spodoptera exigua)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカヨトウ(Spodoptera littoralis)、ハスモンヨトウ(Spodoptera litura)；例えば、オートグラファ属種（Autographa spp.）の、ガンマキンウワバ(Autographa gamma)、タマナギンウワバ(Autographa nigrisigna)；例えば、アグロチス属種(Agrotis spp.)の、タマナヤガ(Agrotis ipsilon)、カブラヤガ(Agrotis segetum)；例えば、ヘリコベルパ属種(Helicoverpa spp.)の、オオタバコガ(Helicoverpa armigera)、タバコガ(Helicoverpaassulta)、コットンボールワーム(Helicoverpa zea)；例えば、ヘリオチス属種(Heliothis spp.)の、ワタキバガ(Heliothis armigera)、ニセアメリカタバコガ(Heliothis virescens)；その他の、ナカジロシタバ(Aedia leucomelas)、ミツモンキンウワバ(Ctenoplusia agnata)、アケビコノハ（Eudocima tyrannus）、ヨトウガ(Mamestra brassicae)、アワヨトウ(Mythimna separata)、フタオビコヤガ(Naranga aenescens)、マツキリガ（Panolis japonica）、ニセタマナヤガ(Peridroma saucia)、ソイビーンルーパー(Pseudoplusia includens)、イラクサギンウワバ(Trichoplusia ni)；
　(m)コブガ科(Nolidae) のガ、例えば、ミスジアオリンガ(Earias insulana)；
　(n)シロチョウ科（Pieridae）のチョウ、例えば、モンシロチョウ属種（Pieris spp.）のオオモンシロチョウ(Pieris brassicae)、モンシロチョウ(Pieris rapae crucivora)；
　(o)コナガ科（Plutellidae）のガ、例えば、アクロレピオプシス属種(Acrolepiopsis spp.)の、ネギコガ(Acrolepiopsis sapporensis)、ヤマノイモコガ(Acrolepiopsis suzukiella)；その他、コナガ(Plutella xylostella)；
　(p)メイガ科（Pyralidae）のガ、例えば、スジマダラメイガ（Cadra cautella）、モロコシマダラメイガ(Elasmopalpus lignosellus)、シロイチモジマダラメイガ(Etiella zinckenella)、ハチノスツヅリガ(Galleria mellonella)；
　(q)スズメガ科（Sphingidae）のガ、例えば、マンジュカ属種(Manduca spp.)の、トマトホーンワーム(Manduca quinquemaculata)、タバコホーンワーム(Manduca sexta)； (k) Moths of the family Lyonetiidae, such as the genus Lyonetia spp., Lyonetia clerkella, Lyonetia prunifoliella malinella;
(l) Noctuidae moths, such as Prodenia spp., Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Fall armyworm Spodoptera exigua, Fall armyworm. ), African Noctuidae (Spodoptera littoralis), Hasmon Noctuidae (Spodoptera litura); For example, Autographa spp. Noctuidae (Agrotis ipsilon), Noctuidae (Agrotis segetum); For example, Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, Cotton ball worm (Helicoverpa zea); The genus (Heliothis spp.), Watakibaga (Heliothis armigera), Fake American tobacco moth (Heliothis virescens); brassicae), Awayoto (Mythimna separata), Futaobikoyaga (Naranga aenescens), Matsukiriga (Panolis japonica), Nisetama nayaga (Peridroma saucia), Soibean looper (Pseudoplusia includens), Irakusagin uwaba (Trichoplusia)
(m) Tuft moth (Nolidae) moths, such as Missia linga (Earias insulana);
(n) Pieridae (Pieridae) butterflies, such as the Pieris spp. Large White (Pieris brassicae), Pieris rapae crucivora;
(o) Plutellidae moths, such as the Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; and other diamondback moths (Plutella xylostella);
(p) Pyralidae moths, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Greater wax moth;
(q) Manduca quinquemaculata, Manduca sexta;
　(r)ニセマイコガ科(Stathmopodidae)のガ、例えば、カキノヘタムシガ(Stathmopoda masinissa)；
　(s)ヒロズコガ科（Tineidae）のガ、例えば、イガ（Tinea translucens）；
　(t)ハマキガ科（Tortricidae）のガ、例えば、アドキソフィエス属種（Adoxophyes spp.）の、チャノコカクモンハマキ(Adoxophyes honmai)、リンゴコカクモンハマキ(Adoxophyes orana)；例えば、アルチプス属種(Archips spp.)の、リンゴモンハマキ(Archips breviplicanus)、ミダレカクモンハマキ(Archips fuscocupreanus)；その他の、トウヒノシントメハマキ(Choristoneura fumiferana)、コドリンガ(Cydia pomonella)、ブドウホソハマキ(Eupoecilia ambiguella)、ナシヒメシンクイ(Grapholitha molesta)、チャハマキ(Homona magnanima)、マメシンクイガ(Leguminivora glycinivorella)、ホソバヒメハマキ(Lobesia botrana)、マメヒメサヤムシガ(Matsumuraeses phaseoli)、トビハマキ(Pandemis heparana)、テングハマキ(Sparganothis pilleriana)；
　(u)スガ科(Yponomeutidae)のガ、例えば、リンゴヒメシンクイ(Argyresthia conjugella)。 (r) Moths of the family Stahtmopodidae, such as the moth Stahmopoda masinissa;
(s) Moths of the clothes moth (Tineidae), such as Iga (Tinea translucens);
(t) Tortrix moths, such as the Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; for example, the Archips spp. ), Apple monhamaki (Archips breviplicanus), Midarekakumonhamaki (Archips fuscocupreanus); ), Chahamaki (Homona magnanima), Mameshiniga (Leguminivora glycinivorella), Hosobahimehamaki (Lobesia botrana), Mamehimesayamushiga (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Tenguhamaki (Sparganothis pill)
(u) Moths of the Ermine moth family (Yponomeutidae), such as the apple fruit moth (Argyresthia conjugella).
（２）アザミウマ目（Thysanoptera）の害虫
　(a)クダアザミウマ科（Phlaeothripidae）の、例えば、カキクダアザミウマ(Ponticulothrips diospyrosi)；
　(b)アザミウマ科（Thripidae）の、例えば、フランクリニェラ属種(Frankliniella spp.)の、ヒラズハナアザミウマ(Frankliniella intonsa)、ミカンキイロアザミウマ(Frankliniella occidentalis)；例えば、トリプス属種（Thrips spp.）の、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci)；その他の、クロトンアザミウマ(Heliothrips haemorrhoidalis)、チャノキイロアザミウマ(Scirtothrips dorsalis)。 (2) Pests of the order Thripidae (Thysanoptera) (a) Thripidae (Phlaeothripidae), for example, Thripidae (Ponticulothrips diospyrosi);
(b) Thripidae, for example Frankliniella spp., Thripidae thripidae, Frankliniella occidentalis; for example, Thrips spp. Thrips palmi, Thrips tabaci; Others, Thripidae (Heliothrips haemorrhoidalis), Western flower thrips (Scirtothrips dorsalis).
（３）カメムシ目（Hemiptera）の害虫
(A)頸吻亜目（Archaeorrhyncha）
　(a)ウンカ科（Delphacidae）の、例えば、ヒメトビウンカ(Laodelphax striatella)、トビイロウンカ(Nilaparvata lugens)、クロフツノウンカ(Perkinsiella saccharicida)、セジロウンカ(Sogatella furcifera)。 (3) Pests of the order Hemiptera
(A) Auchenorrhyncha
(a) Delphacidae, such as Himetobiunka (Laodelphax striatella), Brown planthopper (Nilaparvata lugens), Croftsnounka (Perkinsiella saccharicida), Segatella furcifera.
(B)頸吻亜目（Clypeorrhyncha）
　(a)ヨコバイ科（Cicadellidae）の、例えば、エンポアスカ属種（Empoasca spp.）の、ジャガイモヒメヨコバイ(Empoasca fabae)、カキノヒメヨコバイ(Empoasca nipponica)、チャノミドリヒメヨコバイ(Empoasca onukii)、マメノミドリヒメヨコバイ(Empoasca sakaii)、；その他の、フタテンヒメヨコバイ(Arboridia apicalis)、ミドリナガヨコバイ(Balclutha saltuella)、フタテンオオヨコバイ(Epiacanthus stramineus)、ヒメフタテンヨコバイ(Macrosteles striifrons)、ツマグロヨコバイ(Nephotettix cinctinceps)。 (B) Auchenorrhyncha
(a) Leafhoppers (Cicadellidae), for example, Empoasca spp., Leafhoppers (Empoasca fabae), Leafhoppers (Empoasca nipponica), Chanomidorihimeyokobai (Empoasca onukii), Leafhopper (Empoasca sakaii); Others, Leafhopper (Arboridia apicalis), Empoasca (Balclutha saltuella), Leafhopper (Epiacanthus stramineus), Leafhopper (Macrosteles striifrons) ).
(C)カメムシ亜目（Heteroptera）
　(a)ホソヘリカメムシ科（Alydidae）の、例えば、ホソヘリカメムシ(Riptortus clavatus)；
　(b)ヘリカメムシ科（Coreidae）の、例えば、ホソハリカメムシ(Cletus punctiger)、クモヘリカメムシ(Leptocorisa chinensis)；
　(c)ナガカメムシ科（Lygaeidae）の、例えば、アメリカコバネナガカメムシ(Blissus leucopterus)、カンシャコバネナガカメムシ(Cavelerius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)；
　(d)カスミカメムシ科（Miridae）の、例えば、クロトビカスミカメ(Halticus insularis)、サビイロカスミカメ(Lygus lineolaris)、コットンフリーホッパー(Psuedatomoscelis seriatus)、ナガムギカスミカメ(Stenodema sibiricum)、アカスジカスミカメ(Stenotus rubrovittatus)、イネホソミドリカスミカメ(Trigonotylus caelestialium)； (C) Heteroptera
(a) Riptortus clavatus of the family Alydidae, for example;
(b) Of the leaf-footed bug family (Coreidae), for example, the stink bug (Cletus punctiger), the spider stink bug (Leptocorisa chinensis);
(c) Of the family Lygaeidae, for example, Chinch bug (Blissus leucopterus), Cavelerius saccharivorus, Calabash serrata (Togo hemipterus);
(d) Miridae, for example, Halticus insularis, Lygus lineolaris, Cotton-free hopper (Psuedatomoscelis seriatus), Nagamugi lygus (Stenodema sibiricum), Akasuji lygus (Stenodema sibiricum) ), Rice lygus (Trigonotylus caelestialium);
(e)カメムシ科（Pentatomidae）の、例えば、ネザラ属種（Nezara spp.）の、アオクサカメムシ(Nezara antennata)、ミナミアオカメムシ(Nezara viridula)；例えば、シラホシカメムシ属種（Eysarcoris spp.）の、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、その他の、ブチヒゲカメムシ(Dolycoris baccarum)、ナガメ(Eurydema rugosum)、ツヤアオカメムシ(Glaucias subpunctatus)、サギカメムシ(Halyomorpha halys)、クイチモンジカメムシ(Piezodorus hybneri)、チャバネアオカメムシ(Plautia crossota)、イネクロカメムシ(Scotinophora lurida)；
　(f)ホシカメムシ科（Pyrrhocoridae）の、例えば、アカホシカメムシ(Dysdercus cingulatus)；
　(g)ヒメヘリカメムシ科（Rhopalidae）の、例えば、アカヒメヘリカメムシ(Rhopalus msculatus)；
　(h)キンカメムシ科（Scutelleridae）の、例えば、ムギチャイロカメムシ(Eurygaster
integriceps)；
　(i)グンバイムシ科（Tingidae）の、例えば、ナシグンバイ（Stephanitis nashi）。 (e) Stink bugs (Pentatomidae), for example, Nezara spp., Stink bug (Nezara antennata), Southern green stink bug (Nezara viridula); for example, Stink bug genus (Eysarcoris spp.) , Stink bug (Eysarcoris aeneus), Stink bug (Eysarcoris lewisi), Stink bug (Eysarcoris ventralis), Others, Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum) Halyomorpha halys), stink bug (Piezodorus hybneri), stink bug (Plautia crossota), stink bug (Scotinophora lurida);
(f) Of the red bug family (Pyrrhocoridae), for example, the red bug (Dysdercus cingulatus);
(g) Of the leaf-footed bug family (Rhopalidae), for example, the leaf-footed bug (Rhopalus msculatus);
(h) Scutelleridae, for example, Eurygaster
integriceps);
(i) Tingidae, for example, Stephanitis nashi.
(D)腹吻亜目（Sternorrhyncha）
　(a)カサアブラムシ科（Adelgidae）の、例えば、カラマツカサアブラムシ(Adelges laricis)；
　(b)コナジラミ科（Aleyrodidae）の、例えば、ベミシア属種（Bemisia spp.）の、シルバーリーフコナジラミ(Bemisia argentifolii)、タバココナジラミ(Bemisia tabaci)；その他の、ミカントゲコナジラミ(Aleurocanthus spiniferus)、ミカンコナジラミ(Dialeurodes
citri)、オンシツコナジラミ(Trialeurodes vaporariorum)；
　(c)アブラムシ科（Aphididae）の、例えば、アフィス属種（Aphis spp.）の、マメアブラムシ(Aphis craccivora)、マメクロアブラムシ(Aphis fabae)、イチゴネアブラムシ(Aphis forbesi)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ニワトコアブラムシ(Aphis sambuci)、ユキヤナギアブラムシ(Aphis spiraecola)；例えば、ロパロシフム属種（Rhopalosiphum spp.）の、トウモロコシアブラムシ(Rhopalosiphum maidis)、ムギクビレアブラムシ(Rhopalosiphum padi)；例えば、ジサフィス属種（Dysaphis spp.）の、オオバコアブラムシ(Dysaphis plantaginea)、ギシギシネアブラムシ(Dysaphis radicola)；例えば、マクロシフム属種（Macrosiphum spp.）の、ムギヒゲナガアブラムシ(Macrosiphum avenae)、チューリップヒゲナガアブラムシ(Macrosiphum
euphorbiae)；例えば、ミズス属種（Myzus spp.）の、ニワウメクロコブアブラムシ(Myzus cerasi)、モモアカアブラムシ（Myzus persicae）、カワリコブアブラムシ(Myzus varians)；その他の、エンドウヒゲナガアブラムシ(Acyrthosiphon pisum)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、イチゴケナガアブラムシ(Chaetosiphon fragaefolii)、モモコフキアブラムシ(Hyalopterus pruni)、チシャミドリアブラムシ(Hyperomyzus lactucae)、ニセダイコンアブラムシ（Lipaphis erysimi）、ソラマメヒゲナガアブラムシ(Megoura viciae)、ムギウスイロアブラムシ(Metopolophium dirhodum)、レタスアブラムシ(Nasonovia ribis-nigri)、ホップイボアブラムシ(Phorodonhumuli)、ムギミドリアブラムシ(Schizaphis graminum)、ムギヒゲナガアブラムシ(Sitobion avenae)、コミカンアブラムシ(Toxoptera aurantii)； (D) Sternorrhyncha
(a) Adelgidae, for example, Larch aphid (Adelges laricis);
(b) Whitefly family (Aleyrodidae), for example, Bemisia spp., Silverleaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Other whitefly (Aleurocanthus spiniferus), Whitefly (Dialeurodes
citri), Greenhouse whitefly (Trialeuro des vaporariorum);
(c) Aphididae, for example, Aphis spp., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii ), European apple aphid (Aphis pomi), Niwatokoa aphid (Aphis sambuci), Yukiyanagi aphid (Aphis spiraecola); For example, the aphid (Dysaphis plantaginea), the aphid (Dysaphis radicola) of the genus Dysaphis spp.; Aphid (Macrosiphum)
euphorbiae); For example, of the genus Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; Other, Acyrthosiphon pisum , Potato aphid (Aulacorthum solani), Wheat aphid (Brachycaudus helichrysi), Daikon aphid (Brevicoryne brassicae), Strawberry aphid (Chaetosiphon fragaefolii), Momokofuki aphid (Hyalopter) Daikon aphid (Lipaphis erysimi), Soramamehigenaga aphid (Megoura viciae), Mugius aphid (Metopolophium dirhodum), Lettuce aphid (Nasonovia ribis-nigri), Hopibo aphid (Phorodonhumuli) Aphids (Sitobion avenae), Aphids (Toxoptera aurantii);
　(d)カタカイガラムシ科（Coccidae）の、例えば、セロプラスター属種（Ceroplastes spp.）の、ツノロウムシ(Ceroplastes ceriferus)、ルビーロウムシ(Ceroplastes rubens)；
　(e)マルカイガラムシ科（Diaspididae）の、シューダウラカスピス属種（Pseudaulacaspis spp.）の、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ウメシロカイガラムシ(Pseudaulacaspis prunicola)；例えば、ウナスピス属種（Unaspis spp.）の、マサキナガカイガラムシ(Unaspis euonymi)、ヤノネカイガラムシ(Unaspis yanonensis)；その他の、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Comstockaspis perniciosa)、チャコノハカイガラムシ(Fiorinia theae)、チャノマルカイガラムシ(Pseudaonidia paeoniae)；
　(f)ワタフキカイガラムシ科（Margarodidae）の、例えば、オオワラジカイガラムシ(Drosicha corpulenta)、イセリアカイガラムシ(Icerya purchasi)；
　(g)ネアブラムシ科（Phylloxeridae）の、例えば、ブドウネアブラムシ(Viteus vitifolii)；
　(h)コナカイガラムシ科（Pseudococcidae ）の、例えば、プラノコッカス属種（Planococcus spp.）の、ミカンコナカイガラムシ(Planococcus citri)、フジコナカイガラムシ(Planococcus kuraunhiae)；その他の、ナスコナカイガラムシ(Phenacoccus solani)、クワコナカイガラムシ(Pseudococcus comstocki)；
　(i)キジラミ科（Psyllidae）の、例えば、プスルラ属種（Psylla spp.）の、リンゴキジラミ(Psylla mali)、ナシキジラミ(Psylla pyrisuga)；その他の、ミカンキジラミ(Diaphorina citri)。 (d) Coccidae, for example, Ceroplastes spp., Ceroplastes ceriferus, Ceroplastes rubens;
(e) Diaspididae, Pseudaulacaspis spp., Pseudaulacaspis pentagona, Pseudaulacaspis prunicola; for example, Unaspis spp. Of the scale insects (Unaspis euonymi), Pseudaulacaspis japonicus (Unaspis yanonensis); );
(f) Icerya scale insects (Margarodidae), for example, Owaraji scale insect (Drosicha corpulenta), Iceria scale insect (Icerya purchasi);
(g) Of the family Aphididae (Phylloxeridae), for example, the grape aphid (Viteus vitifolii);
(h) Pseudococcidae, for example, Planococcus spp., Planococcus citri, Planococcus kuraunhiae; Other, Phenacoccus sol , Pseudococcus comstocki;
(i) Psyllidae, eg, Psylla spp., Psylla mali, Psylla pyrisuga; and other Diaphorina citri.
（４）カブトムシ亜目（Polyphaga）の害虫
　(a)シバンムシ科（Anobiidae）の、例えば、タバコシバンムシ(Lasioderma serricorne)； 
　(b)オトシブミ科（Attelabidae）の、例えば、ドロハマキチョッキリ(Byctiscus betulae)、モモチョッキリゾウムシ(Rhynchites heros)；
　(c)ナガシンクイムシ科（Bostrichidae）の、例えば、ヒラタキクイムシ（Lyctus brunneus）；
　(d)ミツギリゾウムシ科（Brentidae）の、例えば、アリモドキゾウムシ(Cylas formicarius)；
　(e)タマムシ科（Buprestidae ）の、例えば、アカバナガタマムシ(Agrilus sinuatus)；
　(f)カミキリムシ科（Cerambycidae）の、例えば、ゴマダラカミキリ(Anoplophora malasiaca)、マツノマダラカミキリ(Monochamus alternatus)、キボシカミキリ(Psacothea hilaris)、ブドウトラカミキリ(Xylotrechus pyrrhoderus)；
　(g)ハムシ科（Chrysomelidae）の、例えば、ブルクス属種（Bruchus spp.）の、エンドウマメゾウムシ(Bruchus pisorum)、ソラマメゾウムシ(Bruchus rufimanus)；例えば、ジアブロチカ属種（Diabrotica spp.）の、ノーザンコーンルートワーム(Diabrotica barberi)、サザンコーンルートワーム(Diabrotica undecimpunctata)、ウエスタンコーンルートワーム(Diabrotica virgifera)；例えば、フィロトレタ属種（Phyllotreta spp.）の、ノミトビヨロイムシ(Phyllotreta nemorum)、キスジノミハムシ(Phyllotreta striolata)；その他の、ウリハムシ(Aulacophora femoralis)、アズキゾウムシ(Callosobruchuschinensis)、カメノコハムシ(Cassida nebulosa)、テンサイトビハムシ(Chaetocnema concinna)、コロラドハムシ（Leptinotarsa decemlineata）、イネクビホソハムシ(Oulema oryzae)、ナスナガスネトビハムシ(Psylliodes angusticollis)； (4) Pests of the suborder Polyphaga (a) Anobiidae, for example, Lasioderma serricorne;
(b) Attelabidae, for example, Byctiscus betulae, Rhynchites heros;
(c) Lyctus brunneus of the family Lyctus brunneus;
(d) Cylas formicarius of the family Curculionidae (Brentidae);
(e) Of the jewel beetle family (Buprestidae), for example, the jewel beetle (Agrilus sinuatus);
(f) Cerambycidae, for example, Anoplophora malasiaca, Monocohamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus;
(g) Chrysomelidae, eg, Bruchus spp., Pea weevil (Bruchus pisorum), Broad bean weevil (Bruchus rufimanus); eg, Diabrotica spp., Northern corn. Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); ); Others, Aulacophora femoralis, Callosobruchuschinensis, Cassida nebulosa, Chaetocnema concinna, Colorado leaf beetle (Leptinotarsa decemlineata), Inekubihosohamushi (Oul) Broad beetle (Psylliodes angusticollis);
　(h)テントウムシ科（Coccinellidae）の、例えば、エピラクナ属種（Epilachna spp.）の、インゲンテントウ(Epilachna varivestis)、ニジュウヤホシテントウ(Epilachna vigintioctopunctata)；
　(i)ゾウムシ科（Curculionidae）の、例えば、アントノムス属種（Anthonomus spp.）の、ワタミゾウムシ(Anthonomus grandis)、ナシハナゾウムシ(Anthonomus pomorum)；例えば、シトフィルスコクゾウムシ属種（Sitophilus spp.）の、グラナリーウィービル(Sitophilus granarius)、コクゾウムシ(Sitophilus zeamais)；その他の、イネゾウムシ(Echinocnemus squameus)、イモゾウムシ(Euscepes postfasciatus)、マツアナアキゾウムシ(Hylobius abietis)、アルファルファタコゾウムシ(Hypera postica)、イネミズゾウムシ(Lissohoptrus oryzophilus)、キンケクチブトゾウムシ(Otiorhynchus sulcatus)、アカアシチビコフキゾウムシ(Sitona lineatus)、シバオサゾウムシ(Sphenophorus venatus)；
　(j)コメツキムシ科（Elateridae）の、例えば、メラノツス属種（Melanotus spp.）の、マルクビクシコメツキ(Melanotus fortnumi)、カンシャクシコメツキ(Melanotus tamsuyensis)；
　(k)ケシキスイ科（Nitidulidae）の、例えば、ヒメヒラタケシキスイ(Epuraea domina)；
　(l)コガネムシ科（Scarabaeidae）の、例えば、アノマラ属種（Anomala spp.）の、ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)；その他の、キンイロハナムグリ(Cetonia aurata)、コアオハナムグリ(Gametis jucunda)、ナガチャコガネ(Heptophylla picea)、ヨーロッパコフキコガネ(Melolontha melolontha)、マメコガネ(Popillia japonica)；
　(m)キクイムシ科（Scolytidae）の、例えば、ヤツバキクイ(Ips typographus)；
　(n)ハネカクシ科（Staphylinidae）の、例えば、アオバアリガタハネカクシ(Paederus
fuscipes)；
　(o)ゴミムシダマシ科（Tenebrionidae）の、例えば、チャイロコメノゴミムシダマシ(Tenebrio molitor)、コクヌストモドキ(Tribolium castaneum)；
　(p)コクヌスト科（Trogossitidae）の、例えば、コクヌスト（Tenebroides mauritanicus）。 (h) Ladybugs (Coccinellidae), for example, Epilacna spp., Mexican bean beetle (Epilachna varivestis), Henosepilachna vigintioctopunctata;
(i) Curculionidae, for example, Anthonomus spp., Anthonomus grandis, Anthonomus pomorum; for example, Sitophilus spp. , Granary Weevils (Sitophilus granarius), Sitophilus zeamais; Others, Weevils (Echinocnemus squameus), Weevils (Euscepes postfasciatus), Weevils (Hylobius abietis) Lissohoptrus oryzophilus), Sitophilus weevil (Otiorhynchus sulcatus), Sitophilus weevil (Sitona lineatus), Sitophilus weevil (Sphenophorus venatus);
(j) Click beetles (Elateridae), for example, Melanotus spp., Melanotus fortnumi, Melanotus tamsuyensis;
(k) Sap beetle (Nitidulidae), for example, Sap beetle (Epuraea domina);
(l) Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; Others, Gametis jucunda, Gametis jucunda ), Nagachakogane (Heptophylla picea), European scarabaeoidea (Melolontha melolontha), Mamekogane (Popillia japonica);
(m) Of the bark beetle family (Scolytidae), for example, the spruce bark (Ips typographus);
(n) Staphylinidae, for example, Paederus littoralis
fuscipes);
(o) Tenebrionidae, for example, Tenebrio molitor, Red flour beetle (Tribolium castaneum);
(p) Of the family Red flour beetle (Trogossitidae), for example, the red flour beetle (Tenebroides mauritanicus).
（５）ハエ目（Diptera）の害虫
(A)ハエ亜目（Brachycera）
　(a)ハモグリバエ科（Agromyzidae）の、例えば、リリオマイザ属種（Liriomyza spp.）の、ナスハモグリバエ(Liriomyza bryoniae)、ネギハモグリバエ(Liriomyza chinensis)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii)；その他の、ナモグリバエ(Chromatomyia horticola)、イネハモグリバエ(Agromyza oryzae)；
　(b)ハナバエ科（Anthomyiidae）の、例えば、デリア属種（Delia spp.）の、タネバエ(Delia platura)、キャベツハナバエ (Delia radicum)；その他の、テンサイモグリハナバエ(Pegomya cunicularia)；
　(c)ショウジョウバエ科（Drosophilidae）の、例えば、ショウジョウバエ属種（Drosophila spp.）の、キイロショウジョウバエ（Drosophila melanogaster）、オウトウショウジョウバエ(Drosophila suzukii)；
　(d)ミギワバエ科（Ephydridae）の、例えば、イネヒメハモグリバエ(Hydrellia griseola)；
　(e)ハネオレバエ科（Psilidae）の、例えば、ニンジンサビバエ(Psila rosae)； 
　(f)ミバエ科（Tephritidae）の、例えば、バクトロセラ属種（Bactrocera spp.）の、ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis)；例えば、ラゴレチス属種（Rhagoletis spp.）の、ヨーロッパオウトウミバエ(Rhagoletis cerasi)、リンゴミバエ(Rhagoletis pomonella)；その他の、チチュウカイミバエ(Ceratitis capitata)、オリーブミバエ(Dacus oleae)。 (5) Diptera pests
(A) Brachycera
(a) Agromyzidae, for example, Agromyzidae (Liriomyza spp.), Agromyzidae (Liriomyza bryoniae), Agromyzidae (Liriomyza chinensis), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza sativae), Agromyzidae (Liriomyza sativae) Others, Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae);
(b) Anthomyiidae, eg, Delia spp., Delia platura, Delia radicum; and other sugar beet, Pegomya cunicularia;
(c) Drosophilidae, for example, Drosophila spp., Drosophila melanogaster, Drosophila suzukii;
(d) Ephydridae, for example, Hydrollia griseola;
(e) From the family Psilidae, for example, the carrot fly (Psila rosae);
(f) Tephritidae, for example, Bactrocera spp., Bactrocera cucurbitae, Bactrocera dorsalis; for example, Rhagoletis spp. Rhagoletis cerasi), Ringomi fly (Rhagoletis pomonella); Others, Chichukai mibae (Ceratitis capitata), Olive mibae (Dacus oleae).
(B)カ亜目（Nematocera）
　(a)タマバエ科（Cecidomyiidae）の、例えば、ダイズサヤタマバエ(Asphondylia yushimai)、ソルガムタマバエ(Contarinia sorghicola)、ヘシアンバエ(Mayetiola destructor)、ムギアカタマバエ(Sitodiplosis mosellana)。 (B) Nematocera
(a) Cecidomyiidae, for example, Soybean Cecidomyiidae, Sorghum sorghicola, Hessian fly (Mayetiola destructor), Mugia caterpillar (Sitodiplosis mosellana).
（６）バッタ目（Orthoptera）の害虫
　(a)バッタ科（Acrididae）の、例えば、スキストセルカ属種（Schistocerca spp.）の、アメリカイナゴ(Schistocerca americana)、サバクトビバッタ(Schistocerca gregaria)；その他の、オーストラリアトビバッタ(Chortoicetes terminifera)、モロッコイナゴ(Dociostaurus maroccanus)、トノサマバッタ(Locusta migratoria)、ブラウンイナゴ(Locustana pardalina)、アカトビバッタ(Nomadacris septemfasciata)、コバネイナゴ(Oxya yezoensis)；
　(b)コオロギ科（Gryllidae）の、例えば、ヨーロッパイエコオロギ(Acheta domestica)、エンマコオロギ(Teleogryllus emma)；
　(c)ケラ科（Gryllotalpidae）の、例えば、ケラ(Gryllotalpa orientalis)；
　(d)キリギリス科（Tettigoniidae）の、例えば、クラズミウマ(Tachycines asynamorus)。 (6) Orthoptera pests (a) Locustaceae (Acrididae), for example, the genus Schistocerca spp., American locust (Schistocerca americana), desert locust (Schistocerca gregaria); Australia Tobibatta (Chortoicetes terminifera), Morocco Inago (Dociostaurus maroccanus), Tonosamabatta (Locusta migratoria), Brown Inago (Locustana pardalina), Akatobibatta (Nomadacris septemfasciata), Kobaneinago (Oxya yezoensis)
(b) Cricket family (Gryllidae), such as European house cricket (Acheta domestica), cricket (Teleogryllus emma);
(c) Mole cricket (Gryllotalpidae), for example, mole cricket (Gryllotalpa orientalis);
(d) Of the Bush cricket family (Tettigoniidae), for example, Tachycines asynamorus.
（７）ダニ類（Acari）
(A)無気門目（Astigmata）のコナダニ類（Acaridida）
　(a)コナダニ科（Acaridae）のダニ、例えば、リゾギルホス属種（Rhizoglyphus spp.）の、ネダニ（Rhizoglyphus echinopus）、ロビンネダニ(Rhizoglyphus robini)；例えば、ケナガコナダニ属種(Tyrophagus spp.)の、オンシツケナガコナダニ(Tyrophagus neiswanderi)、オオケナガコナダニ(Tyrophagus perniciosus)、ケナガコナダニ(Tyrophagusputrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis)；その他、アシブトコナダニ（Acarus siro）、ムギコナダニ（Aleuroglyphus ovatus）、ニセケナガコナダニ（Mycetoglyphus fungivorus)； (7) Mites (Acari)
(A) Acaridida of the order Astigmata
(a) Acaridae mites, such as Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis;
(B)前気門目（Prostigmata）のケダニ類（Actinedida）
　(a)ハダニ科（Tetranychidae）のダニ、例えば、ブリオビア属種（Bryobia spp.）の、クローバーハダニ（Bryobia praetiosa）、ニセクローバーハダニ（Bryobia rubrioculus）；例えば、エオテトラニクス属種（Eotetranychus spp.）の、コウノシロハダニ（Eotetranychus asiaticus）、アンズハダニ（Eotetranychus boreus）、エノキハダニ（Eotetranychus celtis）、ミチノクハダニ（Eotetranychus geniculatus）、ミヤケハダニ（Eotetranychus kankitus）、クリハダニ（Eotetranychus pruni）、シイノキハダニ（Eotetranychus shii）、スミスハダニ（Eotetranychus smithi）、スギナミハダニ（Eotetranychus suginamensis）、クルミハダニ（Eotetranychus uncatus）；例えば、オリゴニクス属種（Oligonychus spp.）の、スギノハダニ（Oligonychus hondoensis）、チビコブハダニ（Oligonychus ilicis）、カラマツハダニ（Oligonychus karamatus）、マンゴーハダニ（Oligonychus mangiferus）、サトウキビハダニ(Oligonychus orthius)、アボガドハダニ（Oligonychus perseae）、エゾスギハダニ（Oligonychus pustulosus）、イネハダニ(Oligonychus shinkajii)、トドマツハダニ（Oligonychus ununguis）；例えば、パノニクス属種(Panonychus spp.)の、ミカンハダニ(Panonychus citri)、クワオオハダニ(Panonychus mori)、リンゴハダニ(Panonychus ulmi)；例えば、テトラニクス属種（Tetranychus spp.）の、ニセナミハダニ（Tetranychus cinnabarinus）、ミツユビナミハダニ（Tetranychus evansi）、カンザワハダニ(Tetranychus kanzawai)、アシノワハダニ（Tetranychus ludeni）、ミズナラハダニ（Tetranychus quercivorus）、サガミハダニ（Tetranychus phaselus）、ナミハダニ(Tetranychusurticae)、オウトウハダニ（Tetranychus viennensis）；例えば、アポニクス属（Aponychus spp.）の、イトマキハダニ（Aponychus corpuzae）、タイリクハダニ（Aponychus firmianae）；例えば、ミドリハダニ属（Sasanychus spp.）の、ミドリハダニ（Sasanychus akitanus）、ヒメミドリハダニ（Sasanychus pusillus）；例えば、シゾテトラニクス属（Shizotetranychus spp.）の、タケスゴモリハダニ（Shizotetranychus celarius）、ケナガスゴモリハダニ（Shizotetranychus longus）、ススキスゴモリハダニ（Shizotetranychus miscanthi）、ヒメササハダニ（Shizotetranychus recki）、ヤナギハダニ（Shizotetranychus schizopus）；その他、カタバミハダニ（Tetranychina harti）、ナミケナガハダニ（Tuckerella pavoniformis）、ケウスハダニ（Yezonychus sapporensis）； (B) Prostigmata prostigmata (Actinedida)
(a) Spider mite (Tetranychidae) mites, such as Bryobia spp., Clover mite (Bryobia praetiosa), fake clover mite (Bryobia rubrioculus); for example, Eotetranychus spp. , Eotetranychus asiaticus, Anzu spider mite (Eotetranychus boreus), Eotetranychus celtis, Michinoku spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus kankitus) (Eotetranychus smithi), Suginami spider mite (Eotetranychus suginamensis), walnut spider mite (Eotetranychus uncatus); Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus perseae), Ezosugi spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), rice spider mite (Oligonychus shinkajii) Panonychus citri, Panonychus mori, Panonychus ulmi; for example, Tetranychus spp., Tetranychus cinnabarinus, Tetranychus cinnabarinus, Tetranychus cinnabarinus, Tetranychus cinnabarinus kanzawai), Asinowa spider mite (T etranychus ludeni), Quercus crispula (Tetranychus quercivorus), Sagami spider mite (Tetranychus phaselus), Nami spider mite (Tetranychusurticae), Oto spider mite (Tetranychus viennensis); Aponychus firmianae); for example, Tetranychus spp., Tetranychus akitanus, Tetranychus pusillus; for example, Shizotetranychus spp. Gasgomori spider mite (Shizotetranychus longus), Susukisugomori spider mite (Shizotetranychus miscanthi), Himesasa spider mite (Shizotetranychus recki), Yanagi spider mite (Shizotetranychus schizopus);
　(b)ヒメハダニ科（Tenuipalpidae）のダニ、例えば、ブレビパルプス属種（Brevipalpus spp.）の、ブドウヒメハダニ（Brevipalpus lewisi）、チャノヒメハダニ（Brevipalpus obovatus）、ミナミヒメハダニ（Brevipalpus phoenicis）、サボテンヒメハダニ（Brevipalpus russulus）、オンシツヒメハダニ（brevipalpus californicus）；例えば、テニパルプス属種（Tenuipalpus spp.）の、ランヒメハダニ（Tenuipalpus pacificus）、カキヒメハダニ（Tenuipalpus zhizhilashviliae）；その他、パイナップルヒメハダニ（Dolichotetranychus floridanus）；
　(c)フシダニ科（Eriophyidae）のダニ、例えば、アセリア属種（Aceria spp.）の、カキサビダニ（Aceria diospyri）、イチジクモンサビダニ（Aceria ficus）、クリフシダニ(Aceria japonica）、クコフシダニ（Aceria kuko）、カーネーションサビダニ（Aceria paradianthi）、クコハモグリダニ（Aceria tiyingi）、チューリップサビダニ(Aceriatulipae)、シバハマキフシダニ（Aceria zoysiea）；例えば、エリオフィエス属種（Eriophyes spp.）の、ニセナシサビダニ(Eriophyes chibaensis)、ウメフシダニ(Eriophyes emarginatae)；例えばアクロプス属種（Aculops spp.）の、トマトサビダニ(Aculops lycopersici)、ミカンサビダニ(Aculops pelekassi)；例えば、アクルス属種（Aculus spp.）の、モモサビダニ（Aculus fockeui）、リンゴサビダニ(Aculus schlechtendali)；その他、チャノナガサビダニ(Acaphylla theavagrans)、チャノサビダニ（Calacarus carinatus）、ブドウハモグリダニ（Colomerus vitis）、ブドウサビダニ（Calepitrimerus vitis）、ナシサビダニ（Epitrimerus pyri）、キンモクサビダニ（Paraphytoptus kikus）、マキサビダニ（Paracalacarus podocarpi）、リュウキュウミカンサビダニ（Phyllocotruta citri）；
　(d)ホコリダニ科（Transonemidae）のダニ、例えば、タルソネムス属種（Tarsonemus spp.）の、スジブトホコリダニ(Tarsonemus bilobatus)、アシボソホコリダニ（Tarsonemus waitei）；その他、シクラメンホコリダニ(Phytonemus pallidus)、チャノホコリダニ(Polyphagotarsonemus latus)；
　(e)ハシリダニ科（Penthaleidae）のダニ、例えば、ペンタレウス属種(Penthaleus spp.)の、ハクサイダニ(Penthaleus erythrocephalus)、ムギダニ(Penthaleus major)。 (b) Tick of the family Tenuipalpidae, for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus phoenicis, Brevipalpus phoenicis russulus), Brevipalpus californicus; For example, Tenuipalpus spp., Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; Other, pineapple zhizhilashviliae;
(c) Eriophyidae mites, such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation. Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes chibaensis, Eriophyes chibaensis ); For example, Tomato sabi tick (Aculops lycopersici) and Mikan sabi tick (Aculops pelekassi) of the genus Acurops (Aculops spp.); ); Others, Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepirimerus vitis, Epitrimerus pyri, Paraphytopa docari ), Phyllocotruta citri;
(d) Tarsonemidae mites, such as Tarsonemus spp., Tarsonemus bilobatus, Tarsonemus waitei; Others, Cyclamen tarsonemidae (Phytonemus pallidus), Polyphagotarsone (Polyphagotarsone) );
(e) Penthaleidae mites, such as Penthaleus spp., Penthaleus erythrocephalus, and Penthaleus major.
　本発明の有害生物防除剤または殺虫若しくは殺ダニ剤は、本発明化合物以外の成分を含有してもよい。他の成分としては、製剤化のために使用する公知の担体などが挙げられる。また、他の成分として、従来公知の、殺菌剤、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、植物調節剤、除草剤、共力剤、肥料、土壌改良剤、動物用飼料などを挙げることができる。このような他の成分を含有することによって、相乗効果を奏することがある。 The pest control agent or insecticide or acaricide of the present invention may contain components other than the compound of the present invention. Examples of other components include known carriers used for formulation. In addition, as other components, conventionally known fungicides, insecticides / acaricides, nematodes, soil pesticides, plant regulators, herbicides, synergists, fertilizers, soil conditioners, animal feeds And so on. By containing such other components, a synergistic effect may be produced.
　本発明の有害生物防除剤または殺虫若しくは殺ダニ剤と混用または併用することができる、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、駆虫剤などの具体例を以下に示す。 Specific examples of insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
（１Ａ）アセチルコリンエステラーゼ（AChE）阻害剤（カーバメート系）
　アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、ブトカルボキシム、 ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、メトルカルブ、オキサミル、ピリミカーブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、ＸＭＣ、キシリルカルブ。
　アルドキシカルブ、アリキシカルブ、アミノカルブ、ブフェンカルブ、クロエトカルブ、フェノチオカルブ、プロメカルブ。
（１Ｂ）アセチルコリンエステラーゼ（AChE）阻害剤（有機リン系）
　アセフェート、アザメチホス、アジンホスエチル、アジンホスメチル、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、ジメトン-S-メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、ジスルホトン、ＥＰＮ、エチオン、エトプロホス、ファンフル、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピル=O-(メトキシアミノチオホスホリル)サリチラート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレッド、オメトエート、オキシジメトンメチル、パラチオン、パラチオンメチル、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホスメチル、プロフェノホス、プロペタムホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリムホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン。
　ブロモホス－エチル、シアノフェンホス、デメトン－Ｓ－メチルスルホン、ジアリホス、ジクロフェンチオン、ジオキサベンゾホス、エトリムホス、フェンスルホチオン、ホノホス、ホルモチオン、ヨードフェンホス、イサゾホス、イソカルボホス、メタクリホス、ホスホカルブ、ピリミホス－エチル、プロパホス、プロトエート、スルプロホス。 (1A) Acetylcholinesterase (AChE) inhibitor (carbamate type)
Aranicarb, Aldicarb, Bendiocarb, Benfracarb, Butocarboxim, Butoxycarboxym, Carbaryl, Carbofuran, Carbosulfan, Ethiophenate, Phenocalve, Formethanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamil, Pyrimicurve, Propoxul Thiophanox, Triazamate, Trimetacarb, XMC, Kisilylcarb.
Aldoxycarb, Alixicalve, Aminocarb, Bufencarb, Chloetcarb, Phenothiocarb, Promecarb.
(1B) Acetylcholinesterase (AChE) inhibitor (organophosphorus)
Acefate, Azamethifos, Adinphosethyl, Adinphosmethyl, Cazsaphos, Chlorpyrifos, Chlorpyrifos, Chlormefos, Chlorpyrifos, Chlorpyrifosmethyl, Kumaphos, Cyanophos, Dimethon-S-methyl, Diazinon, Dichlorbos, Dicrotophos, Dimethate, Dimethylbinphos, Disulfoton, EPN Ethion, etoplophos, funful, fenitrothion, fenitrothion, fenitrothion, hostiazeto, heptenophos, imiciaphos, isophenphos, isopropyl = O- (methoxyaminothiophosphoryl) salicylate, isoxathione, malathion, mecarbam, methamidophos, metidathion, mevinphos, chlorpyrifos, nared Ometoate, Oxydimetone Methyl, Parathion, Parathion Methyl, Fentate, Holate, Hosalon, Hosmet, Phosphamide, Hoxim, Pyrimiphos Methyl, Profenophos, Propetamphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrimphos, Temefos, Telbuphos, Tebupyrifos Thiometon, triazophos, trichlorfon, bamidion.
Bromophos-ethyl, cyanophenphos, demeton-S-methylsulfone, dialifor, diclofenthion, dioxabenzophos, etrimphos, phensulfotion, honofos, formotione, iodophenphos, isazophos, isocarbhos, methacryphos, phosphocarb, pyrimiphos-ethyl, propaphos, Protoate, sulprophos.
（２）GABA作動性塩化物イオン(塩素イオン)チャネルブロッカー
　クロルデン、エンドスルファン；エチプロール、フィプロニル。
　アセトプロール、カンフェクロル、ジエノクロル、ヘプタクロル、ピラフルプロール、ピリプロール；フルフィプロル。
（３Ａ）ナトリウムチャネルモジュレーター（ピレスロイド系）
　アクリナトリン、アレスリン、d-シス-トランス-アレスリン、d-トランス-アレスリン、ビフェントリン、ビオアレスリン、ビオアレスリン-S-シクロペンテニル-異性体、ビオレスメトリン、シクロプロトリン、シフルトリン、β-シフルトリン、シハロトリン、λ-シハロトリン、γ-シハロトリン、シペルメトリン、α-シペルメトリン、β-シペルメトリン、θ-シペルメトリン、ζ-シペルメトリン、シフェノトリン[(1R)-トランス異性体]、デルタメトリン、エンペントリン[(EZ)-(1R)-異性体]、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、τ-フルバリネート、ハルフェンプロックス、イミプロトリン、カデスリン、ペルメトリン、フェノトリン[(1R)-トランス異性体]、プラレトリン、ピレトリン、レスメトリン、シラフルオフェン、テフルトリン、テトラメスリン、テトラメスリン[(1R)-異性体]、トラロメトリン、トランスフルトリン。
　κ-ビフェントリン、ビオペルメトリン、クロロプラレスリン、ジメフルトリン、フェンフルトリン、フェンピリトリン、フルフェンプロックス、ヘプタフルスリン、メペルフルスリン、ε-メトフルトリン、モンフルオロトリン、ε-モンフルオロトリン、トランス-ペルメトリン、プロフルトリン、プロトリフェンブト、κ-テフルトリン、テラレトリン、テトラメチルフルスリン；ビオエタノメトリン。
（３Ｂ）ナトリウムチャネルモジュレーター（ＤＤＴ類）
　ＤＤＴ、メトキシクロル。 (2) GABAergic chloride ion (chlorine ion) channel blocker Chlordane, endosulfan; etiprol, fipronil.
Acetoprowl, camfechlor, dienochlor, heptachlor, pilafprowl, pilafrol; fulfiprol.
(3A) Sodium channel modulator (pyrethroid)
Acrinathrin, Aresrin, d-cis-trans-Aresulin, d-trans-Aresrin, bifentrin, bioaresrin, bioaresrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cypermethrin, β-cypermethrin, cypermethrin, λ- Cypermethrin, γ-cypermethrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cypermethrin [(1R) -trans isomer], deltamethrin, empentrin [(EZ)-( 1R)-isomer], esphenvalerate, etofenprox, phenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halphenprox, imiprothrin, cadesrin, permethrin, phenothrin [(1R) -trans Heterogeneous], permethrin, pyrethrin, allethrin, cypermethrin, tefluthrin, tetramethrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin.
κ-bifenthrin, biopermethrin, chloropralesrin, dimefluthrin, fenfurthrin, fenpyritrin, flufenprox, heptafluthrin, meperfluthrin, ε-methfurthrin, monfluorothrin, ε-monfluorothrin, trans-permethrin, profluthrin , Protrifenbut, κ-tefluthrin, terraretrin, tetramethylfluthrin; bioetanomethrin.
(3B) Sodium channel modulators (DDTs)
DDT, methoxychlor.
（４）ニコチン性アセチルコリン受容体(nAChR)競合的モジュレーター
　アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム；ニコチン；スルホキサフロル；フルピラジフロン；トリフルメゾピリム。
　ニチアジン；ジクロロメゾチアズ、フルピリミン。
（５）ニコチン性アセチルコリン受容体(nAChR)アロステリックモジュレーター
　スピネトラム、スピノサド。
（６）グルタミン酸作動性塩化物イオン(塩素イオン)チャネル(GluCl) アロステリックモジュレーター
　アバメクチン、エマメクチン、エマメクチン安息香酸塩、レピメクチン、ミルベメクチン。
　ドラメクチン、エプリノメクチン、イベルメクチン、モキシデクチン、セラメクチン。
（７）幼若ホルモン類似剤
　ヒドロプレン、キノプレン、メトプレン；フェノキシカルブ；ピリプロキシフェン。
　ジオフェノラン、エポフェノナン、トリプレン。
（８）その他の非特異的(マルチサイト)阻害剤
　臭化メチル、ハロゲン化アルキル類；クロルピクリン；弗化アルミニウムナトリウム、フッ化スルフリル；ホウ砂、ホウ酸、オクタホウ酸ニナトリウム塩、ホウ酸ナトリウム塩、メタホウ酸ナトリウム塩；吐酒石；ダゾメット、メタム、メタムカリウム塩、メタムナトリウム塩。
（９）弦音器官TRPVチャネルモジュレーター
　ピメトロジン、ピリフルキナゾン；アフィドピロペン。
（１０）ダニ類成長阻害剤
　クロフェンテジン、ジフロビダジン、ヘキシチアゾクス；エトキサゾール。 (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradiflon; triflumesopirim.
Nichiazine; dichloromethane, dichloromethane.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulator Spinosad, spinosad.
(6) Glutamic Acidic Chloride Ion (Chloride Ion) Channel (GluCl) Allosteric Modulator Abamectin, Emamectin, Emamectin Benzoate, Repimectin, Milbemectin.
Doramectin, eprinomectin, ivermectin, moxidectin, selamectin.
(7) Juvenile hormone analogs Hydroprene, quinoprene, methoprene; phenoxycarb; pyriproxyfen.
Geophenoran, Epophenonan, Triplen.
(8) Other non-specific (multisite) inhibitors Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfryl fluoride; borax, boric acid, disodium octaborate salt, sodium borate salt , Sodium metaborate; borax; Dazomet, metam, metam potassium salt, metam sodium salt.
(9) String organ TRPV channel modulator Pimetrodin, pyrifluquinazone; Afidopyropen.
(10) Tick growth inhibitors clofentezine, difluorovidazine, hexitiazox; etoxazole.
（１１）微生物由来昆虫中腸内膜破壊剤
　B.t. subsp. israelensis、B.t. subsp. aizawai、B.t. subsp. kurstaki、B.t. subsp. tenebrionis；B.t.作物に含まれるタンパク質：Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、 Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1；Bacillus sphaericus。
（１２）ミトコンドリアATP合成酵素阻害剤
　ジアフェンチウロン；アゾシクロチン、シヘキサチン、酸化フェンブタスズ；プロパルギット；テトラジホン。
（１３）プロトン勾配を撹乱する酸化的リン酸化脱共役剤
　クロルフェナピル、ＤＮＯＣ、スルフルラミド。
　ビナパクリル、ジノブトン、ジノカップ。
（１４）ニコチン性アセチルコリン受容体(nAChR)チャネルブロッカー
　ベンスルタップ、カルタップ塩酸塩、チオシクラム、チオスルタップ－ナトリウム塩。
（１５）キチン生合成阻害剤、タイプ０
　ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン。
　フルアズロン。
（１６）キチン生合成阻害剤、タイプ１
　ブプロフェジン。
（１７）脱皮阻害剤
　シロマジン。
（１８）脱皮ホルモン(エクダイソン)受容体アゴニスト
　クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド。 (11) Insects derived from microorganisms Bt subsp. Israelensis, Bt subsp. Aizawai, Bt subsp. Kurstaki, Bt subsp. Tenebrionis; Proteins contained in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab , Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus.
(12) Mitochondrial ATP synthase inhibitor diafenthurone; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradiphon.
(13) Oxidative phosphorylation uncoupler that disturbs the proton gradient Chlorfenapyr, DNOC, sulfuramide.
Binapacryl, Ginobuton, Ginocup.
(14) Nicotinic Acetylcholine Receptor (nAChR) Channel Blocker Bensultap, Cartap Hydrochloride, Nereistoxin, Thiosultap-Sodium Salt.
(15) Chitin biosynthesis inhibitor, type 0
Bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflumron.
Full Azlon.
(16) Chitin biosynthesis inhibitor, type 1
Buprofezin.
(17) Cyromazine, a molting inhibitor.
(18) Molting hormone (ecdysone) receptor agonist chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
（１９）オクトパミン受容体アゴニスト
　アミトラズ。
　クロルジメホルム。
（２０）ミトコンドリア電子伝達系複合体III阻害剤
　ヒドラメチルノン；アセキノシル；フルアクリピリム；ビフェナゼート。
（２１）ミトコンドリア電子伝達系複合体I阻害剤(METI)
　フェナザキン、フェンピロキシメート、ピリダベン、ピリミジフェン、テブフェンピラド、トルフェンピラド；ロテノン。
（２２）電位依存性ナトリウムチャネルブロッカー
　インドキサカルブ；メタフルミゾン。
（２３）アセチルCoAカルボキシラーゼ阻害剤
　スピロジクロフェン、スピロメシフェン、スピロテトラマト。
　スピロピジオン。
（２４）ミトコンドリア電子伝達系複合体IV阻害剤
　リン化アルミニウム、リン化カルシウム、リン化亜鉛（Zn-phosphide）、ホスフィン；シアン化カルシウム、シアン化ナトリウム、シアン化カリウム。
（２５）ミトコンドリア電子伝達系複合体II阻害剤
　シエノピラフェン、シフルメトフェン；ピフルブミド。 (19) Octopamine receptor agonist Amitraz.
Chlorjimeholm.
(20) Mitochondrial electron transport chain complex III inhibitor Hydramethylnon; acequinocyl; fluacripirim; biphenazate.
(21) Mitochondrial electron transport chain complex I inhibitor (METI)
Phenazakin, phenpyroximate, pyridaben, pyrimidifen, tebufenpyrado, tolfenpyrad; rotenone.
(22) Voltage-gated sodium channel blocker Indoxacarb; metaflumison.
(23) Acetyl-CoA carboxylase inhibitor Spirodiclophen, spiromesiphen, spirotetramato.
Spiropidion.
(24) Mitochondrial electron transfer system complex IV inhibitor Aluminum phosphide, calcium phosphide, zinc phosphide (Zn-phosphide), phosphine; calcium cyanide, sodium cyanide, potassium cyanide.
(25) Mitochondrial electron transport chain complex II inhibitor Sienopyraphen, siflumethofen; pifrubmid.
（２８）リアノジン受容体モジュレーター
　クロラントラニリプロール、シアントラニリプロール、シクラニリプロール、フルベンジアミド。
　シハロジアミド、テトラクロラントラニリプロール、テトラニリプロール。
（２９）弦音器官モジュレーター 標的部位未特定
　フロニカミド。
（３０）ＧＡＢＡ作動性塩化物イオン(塩素イオン)チャネルアロステリックモジュレーター
　ブロフラニリド、フルキサメタミド。
　イソシクロセラム；アフォキソラネル、フルララネル、ロチラネル、サロラネル。
（３１）その他の殺虫剤、殺ダニ剤
　アザジラクチン、ベンゾキシメート、ブロモプロピレート、キノメチオナート、ジコホル、石灰硫黄合剤、マンコゼブ、ピリダリル、硫黄。
　アシノナピル、アミドフルメット、ベンゾメート、ベンズピリモキサン、クロルベンジレート、ジシクラニル、フェノキサクリム、フェントリファニル、フロメトキン、フルベンジミン、フルフェンジン、フルヘキサホン、フルオピラム、メタフルミゾン、メトキサジアゾン、オキサゾスルフィル、テトラスル、トリアラセン、チクロピラゾフロル。 (28) Ryanodine receptor modulators Chloranthraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide.
Cyantraniliprole, tetrachlorantraniliprole, tetraniliprole.
(29) String sound organ modulator Target site unspecified Fronicamid.
(30) GABAergic Chloride Ion (Chlorine Ion) Channel Allosteric Modulator Brofuranilide, Fluxamethamide.
Isocycloserum; afoxolanel, full lalanel, rotilanel, salolanel.
(31) Other insecticides, acaricides Azadirachtin, benzoximate, bromopropilate, quinomethionate, dicofol, lime sulfur, mancozeb, pyridalyl, sulfur.
Asinonapill, Amidoflumet, Benzomate, Benzpyrimoxane, Chlorobenzilate, Disicranil, Phenoxacrim, Fentrifanyl, Frometkin, Flubendimin, Flufendin, Fullhexaphone, Fluopirum, Metaflumison, Metoxadiazone, Oxadiazole, Tetrasul, Triarasen, Cycro Pyrazoflor.
（３２）駆虫剤：
　(a)ベンズイミダゾール系：　フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール、メベンダゾール、オクスフェンダゾール、パーベンダゾール、フルベンダゾール、フェバンテル、ネトビミン、チオファネート、チアベンダゾール、カンベンダゾール；
　(b)サリチルアニリド系：　クロサンテル、オキシクロザニド、ラフォキサニド、ニクロサミド；
　(c)置換フェノール系：　ニトロキシニル、ニトロスカネート；
　(d)ピリミジン系：　ピランテル、モランテル；
　(e)イミダゾチアゾール系：　レバミソール、テトラミソール；
　(f)テトラヒドロピリミジン系：　プラジカンテル、エプシプランテル；
　(g)その他の駆虫薬：　シクロジエン、リアニア、クロルスロン、メトロニダゾール、デミジトラズ、ピペラジン、ジエチルカルバマジン、ジクロロフェン、モネパンテル、トリベンジミジン、アミダンテル、チアセタルサミド、メロルサミン、アルセナマイド。 (32) Anthelmintic:
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, fevantel, netobimin, thiophanate, thiabendazole, cambendazole;
(b) Salicylanilides: closantel, oxyclozanide, lafoxanide, niclosamide;
(c) Substituted phenolic system: nitroxynyl, nitroscanate;
(d) Pyrimidines: Pyrantel, Morantel;
(e) Imidazothiazoles: levamisole, tetramisole;
(f) Tetrahydropyrimidines: Praziquantel, Epsiprantel;
(g) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetalsamide, merolsamine, arsenamide.
　本発明の有害生物防除剤または殺虫若しくは殺ダニ剤と混用または併用することができる、殺菌剤の具体例を以下に示す。
（１）核酸生合成阻害剤：
　(a)RNAポリメラーゼＩ阻害剤：　ベナラキシル、ベナラキシル-M、フララキシル、メタラキシル、メタラキシル-M、オキサジキシル、クロジラコン、オフレース；
　(b)アデノシンデアミナーゼ阻害剤：　ブピリメート、ジメチリモール、エチリモール；
　(c)DNA/RNA合成阻害剤：　ヒメキサゾール、オクチリノン；
　(d)DNAトポイソメラーゼII阻害剤：　オキソリン酸。 Specific examples of fungicides that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitor:
(a) RNA polymerase I Inhibitors: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M, Oxadixil, Closilacon, Offrace;
(b) Adenosine deaminase inhibitors: bupirimate, dimethilimol, etilimol;
(c) DNA / RNA synthesis inhibitors: himexazole, octylinone;
(d) DNA topoisomerase II inhibitor: oxolinic acid.
（２）有糸核分裂阻害剤および細胞分裂阻害剤：
　(a)β－チューブリン重合阻害剤：　ベノミル、カルベンダジム、クロルフェナゾール、フベリダゾール、チアベンダゾール、チオファネート、チオファネートメチル、ジエトフェンカルブ、ゾキサミド、エタボキサム；
　(b)細胞分裂阻害剤：　ペンシクロン；
　(c)スペクトリン様タンパク質の非局在化阻害剤：　フルオピコリド。 (2) Mitotic and fission inhibitors:
(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, dietofencarb, zoxamide, etaboxam;
(b) Cell division inhibitor: pencyclon;
(c) Spectrin-like protein delocalization inhibitor: fluoricolide.
（３）呼吸阻害剤：
　(a)複合体I NADH酸化還元酵素阻害剤：　ジフルメトリム、トルフェンピラド；
　(b)複合体IIコハク酸脱水素酵素阻害剤：　ベノダニル、フルトラニル、メプロニル、イソフェタミド、フルオピラム、フェンフラム、フルメシクロックス、カルボキシン、オキシカルボキシン、チフルザミド、ベンゾビンジフルピル、ビキサフェン、フルキサピロキサド、フラメトピル、イソピラザム、ペンフルフェン、ペンチオピラド、セダキサン、ボスカリド、ピラジフルミド；
　(c)複合体IIIユビキノールオキシダーゼQo阻害剤：　アゾキシストロビン、クモキシストロビン、クメトキシストロビン、エノキサストロビン、フルフェノキシストロビン、ピコキシストロビン、ピラオキシストロビン、ピラクロストロビン、ピラメトストロビン、トリクロピリカルブ、クレソキシム-メチル、トリフロキシストロビン、ジモキシストロビン、フェナミンストロビン、メトミノストロビン、オリサストロビン、ファモキサドン、フルオキサストロビン、フェンアミドン、ピリベンカルブ、マンデストロビン；
　(d)複合体IIIユビキノール還元酵素Qi阻害剤：　シアゾファミド、アミスルブロム；
　(e)酸化的リン酸化の脱共役剤：　ビナパクリル、メプチルジノカップ、ジノカップ、フルアジナム、フェリムゾン；
　(f)酸化的リン酸化阻害剤(ATP 合成酵素の阻害剤)：　フェンチンアセテート、塩化フェンチン、水酸化フェンチン；
　(g)ATP生産阻害剤：　シルチオファム；
　(h)複合体III：シトクロームbc1(ユビキノン還元酵素)のQx(未知)阻害剤：　アメトクトラジン。 (3) Respiratory inhibitor:
(a) Complex I NADH Oxidoreductase Inhibitors: Diflumetrim, Torphenpyrad;
(b) Complex II succinate dehydrogenase inhibitor: benodanyl, flutranyl, mepronil, isofetamide, fluopirum, fenfuram, flumecyclox, carboxin, oxycarboxin, thyfluzamide, benzobindiflupill, bixaphen, fluxapyroxado , Flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan, boscalide, pyraziflumid;
(c) Complex III Ubiquinol Oxidase Qo Inhibitors: Azoxystrobin, Spiderxtrobin, Kumethoxystrobin, Enokistrobin, Fluphenoxystrobin, Picoxystrobin, Pyraoxystrobin, Pyracrostrobin, Pyrametostrobin, triclopyricalve, cresoxime-methyl, trifloxystrobin, dymoxystrobin, phenaminestrobin, metminostrobin, orisastrobin, famoxadon, fluoroxastrobin, fenamiden, pyribenecarb, mandestrobin;
(d) Complex III Ubiquinol Reductase Qi Inhibitors: Ciazofamide, Amisulbrom;
(e) Oxidative phosphorylation uncoupler: binapacryl, meptylzinocup, dinocup, fluazinum, ferlimzone;
(f) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethoctrazine.
（４）アミノ酸およびタンパク質合成阻害剤
　(a)メチオニン生合成阻害剤：　アンドプリム、シプロジニル、メパニピリム、ピリメタニル；
　(b)タンパク質合成阻害剤：　ブラストサイジン-Ｓ、カスガマイシン、カスガマイシン塩酸塩、ストレプトマイシン、オキシテトラサイクリン。 (4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl;
(b) Protein synthesis inhibitors: Blasticidin-S, casugamycin, casugamycin hydrochloride, streptomycin, oxytetracycline.
（５）シグナル伝達阻害剤：
　(a)シグナル伝達阻害剤：　キノキシフェン、プロキナジド；
　(b)浸透圧シグナル伝達におけるMAP・ヒスチジンキナーゼ阻害剤：　フェンピクロニル、フルジオキソニル、クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン。 (5) Signal transduction inhibitor:
(a) Signal transduction inhibitors: quinoxyphen, proquinazide;
(b) MAP / histidine kinase inhibitors in osmotic signaling: fenpicronyl, fludioxonyl, clozolineate, iprodion, procymidone, vinclozoline.
（６）脂質および細胞膜合成阻害剤：
　(a)りん脂質生合成、メチルトランスフェラーゼ阻害剤：　エジフェンホス、イプロベンホス、ピラゾホス、イソプロチオラン；
　(b)脂質の過酸化剤：　ビフェニル、クロロネブ、ジクロラン、キントゼン、テクナゼン、トルクロホスメチル、エトリジアゾール；
　(c)細胞膜に作用する剤：　ヨードカルブ、プロパモカルブ、プロパモカルブ塩酸塩、プロパモカルブホセチレート、プロチオカルブ；
　(d)病原菌細胞膜を撹乱する微生物：　バチルスズブチリス菌、バチルスズブチリスQST713 株、バチルスズブチリスFZB24 株、バチルスズブチリスMBI600 株、バチルスズブチリスD747株；
　(e)細胞膜を撹乱する剤：　ゴセイカユプテ(ティーツリー)の抽出物。 (6) Lipid and cell membrane synthesis inhibitor:
(a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenphos, pyrazophos, isoprothiolane;
(b) Lipid peroxidizers: biphenyl, chloroneb, dichloran, quintozen, technazen, toluclophosmethyl, etridiazole;
(c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb Josetilate, prothiocarb;
(d) Pathogens Microorganisms that disrupt cell membranes: Bacillus bacillus, Bacillus bacillus QST713, Bacillus bacillus FZB24, Bacillus bacillus MBI600, Bacillus chinensis D747;
(e) Agent that disturbs cell membranes: Extract of Gosei Kayupte (tea tree).
（７）細胞膜のステロール生合成阻害剤：
　(a)ステロール生合成におけるC14位の脱メチル化阻害剤：　トリホリン、ピリフェノックス、ピリソキサゾール、フェナリモル、フルルプリミドール、ヌアリモル、イマザリル、イマザリル硫酸塩、オキスポコナゾール、ペフラゾエート、プロクロラズ、トリフルミゾール、ビニコナゾール、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジクロブトラゾール、ジフェノコナゾール、ジニコナゾール、ジニコナゾール-M、エポキシコナゾール、エタコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホール、フルコナゾール、フルコナゾール－シス、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、プロチオコナゾール、ボリコナゾール、メフェントリフルコナゾール；
　(b)ステロール生合成におけるΔ14還元酵素およびΔ8→Δ7－イソメラーゼの阻害剤：
　アルジモルフ、ドデモルフ、ドデモルフ酢酸塩、フェンプロピモルフ、トリデモルフ、フェンプロピジン、ピペラリン、スピロキサミン；
　(c)ステロール生合成系のC4位脱メチル化における3-ケト還元酵素阻害剤：　フェンヘキサミド、フェンピラザミン；
　(d)ステロール生合成系のスクワレンエポキシダーゼ阻害剤：　ピリブチカルブ、ナフチフィン、テルビナフィン。 (7) Cell membrane sterol biosynthesis inhibitor:
(a) Demethylation inhibitor at position C14 in sterol biosynthesis: trifoline, pyrifenox, pyrisoxazole, phenalimol, fluconazole, nuarimol, imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloraz, triflumizole , Biniconazole, azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triazimefone, triazimenol, triticonazole, prothioconazole, voriconazole, mephen Trifluconazole;
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, Dodemorph, Dodemorph Acetate, Fenpropimorph, Tridemorph, Fenpropidine, Piperline, Spiroxamine;
(c) 3-ketoreducing enzyme inhibitors in C4 demethylation of sterol biosynthesis system: fenhexamide, fenpyrazamine;
(d) Sterol biosynthetic squalene epoxydase inhibitors: pyribuchicarb, naftifine, terbinafine.
（８）細胞壁合成阻害
　(a)トレハラーゼ阻害剤：　バリダマイシン；
　(b)キチン合成酵素阻害剤：　ポリオキシン、ポリオクソリム；
　(c)セルロース合成酵素阻害剤：　ジメトモルフ、フルモルフ、ピリモルフ、ベンチアバリカルブ、イプロバリカルブ、トルプロカルブ、バリフェナレート、マンジプロパミド。 (8) Inhibition of cell wall synthesis (a) Trehalase inhibitor: Validamycin;
(b) Chitin synthase inhibitors: polyoxin, polyoxolim;
(c) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph, Bench Avaricarb, Iprovaricarb, Torprocarb, Variphenalate, Mandipropamide.
（９）メラニン生合成阻害剤
　(a)メラニン生合成の還元酵素阻害剤：　フサライド、ピロキロン、トリシクラゾール；
　(b)メラニン生合成の脱水酵素阻害剤：　カルプロパミド、ジクロシメット、フェノキサニル。 (9) Melanin biosynthesis inhibitor (a) Melanin biosynthesis reductase inhibitor: fusalide, pyroquilon, tricyclazole;
(b) Dehydrating enzyme inhibitors of melanin biosynthesis: calpropamide, diclosimet, phenoxanyl.
（１０）宿主植物の抵抗性誘導剤：
　(a)サリチル酸合成経路に作用する剤：　アシベンゾラル-S-メチル；
　(b)その他：　プロベナゾール、チアジニル、イソチアニル、ラミナリン、オオイタドリ抽出液。 (10) Host plant resistance inducer:
(a) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: probenazole, thiazinyl, isothianil, laminarin, Reynoutria sachalinensis extract.
（１１）作用性が不明な剤：　シモキサニル、ホセチルアルミニウム、リン酸(リン酸塩)、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、メタスルホカルブ、シフルフェナミド、メトラフェノン、ピリオフェノン、ドジン、ドジン遊離塩基、フルチアニル。 (11) Agents of unknown activity: simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.
（１２）多作用点を有する剤：　銅(銅塩)、ボルドー液、水酸化銅、銅ナフタレート、酸化銅、オキシ塩化銅、硫酸銅、硫黄、硫黄製品、多硫化カルシウム、ファーバム、マンコゼブ、マネブ、マンカッパー、メチラム、ポリカーバメート、プロピネブ、チラム、ジネブ、ジラム、キャプタン、カプタホール、フォルペット、クロロタロニル、ジクロフルアニド、トリルフルアニド、グアザチン、グアザチン酢酸塩、イミノクタジン酢酸塩(iminoctadine triacetate)、イミノクタジンアルベシル酸塩(iminoctadine trialbesilate) 、アニラジン、ジチアノン、キノメチオネート、フルオルイミド。 (12) Agents with multi-action points: Copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbum, mancozeb, maneb, Man copper, methylam, polycarbamate, propineb, tiram, dineb, dilam, captan, captahole, folpet, chlorotalonyl, diclofluanide, trillfluanide, guazatin, guazatin acetate, iminoctadine triacetate, iminoctadine albecil Iminoctadine trial besilate, anilazine, dithianone, quinomethionate, fluorimide.
（１３）その他の剤：　DBEDC、フルオロフォルペット、ビス(8-キノリノラト)銅(II)、プロパミジン、クロロピクリン、シプロフラム、アグロバクテリウム、ベトキサジン、ジフェニルアミン、メチルイソチアネート(MITC)、ミルデオマイシン、カプサイシン、クフラネブ、シプロスルファミド、ダゾメット、デバカルブ、ジクロロフェン、ジフェンゾクワット、ジフェンゾクワットメチルスルホネート、フルメトベル、ホセチルカルシウム、ホセチルナトリウム、イルママイシン、ナタマイシン、ニトロタールイソプロピル、オキサモカルブ、ピロールニトリン、テブフロキン、トルニファニド、ザリラミド、アルゴフェーズ(Algophase)、アミカルチアゾール(Amicarthiazol)、オキサチアピプロリン(Oxathiapiprolin)、メチラム亜鉛、ベンチアゾール、トリクラミド、ユニコナゾール、オキシフェンチイン(Oxyfenthiin)、ピカルブトラゾクス(picarbutrazox)、フェンピコキサミド（Fenpicoxamid）、ジクロベンチアゾクス（dichlobentiazox）、キノフメリン（Quinofumelin）。 (13) Other agents: DBEDC, fluorofolpet, bis (8-quinolinolato) copper (II), propamidin, chloropyrrolnitrin, cyprofulum, agrobacterium, betoxazine, diphenylamine, methylisothianate (MITC), mildeomycin , Capsaicin, Kufraneb, Ciprosulfamide, Dazomet, Devacarb, Dichlorophene, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumetbel, Josetylcalcium, Josetilsodium, Irumamycin, Natamycin, Nitrotalisopropyl, Oxamocarb, Pyrrolnitrin Oxathiapiprolin, Methylamzinc, Benchazole, Triclamid, Uniconazole, Oxyfenthiin, Picalbutrazox (picarbutrazox), Fenpicoxamid, dichlobentiazox, Quinofumelin.
　本発明の有害生物防除剤または殺虫若しくは殺ダニ剤と混用または併用することができる、植物調節剤の具体例を以下に示す。
　１－メチルシクロプロペン、２，３，５－トリヨード安息香酸、ＩＡＡ、ＩＢＡ、ＭＣＰＡ、ＭＣＰＢ、４－ＣＰＡ、５－アミノレブリン酸塩酸塩、６－ベンジルアミノプリン、アブシシン酸、アビグリシン塩酸塩、アンシミドール、ブトルアリン、炭酸カルシウム、塩化カルシウム、ギ酸カルシウム、過酸化カルシウム、石灰硫黄、硫酸カルシウム、クロルメコートクロリド、クロロプロファム、塩化コリン、クロプロップ、シアナミド、シクラニリド、ダミノジッド、デシルアルコール、ジクロルプロップ、ジケグラック、ジメチピン、ジクワット、エテホン、エチクロゼート、フルメトラリン、フルルプリミドール、ホルクロルフェヌロン、ジベレリンＡ、ジベレリンＡ３、ヒメキサゾール、イナベンフィド、イソプロチオラン、カイネチン、マレイン酸ヒドラジド、メフルイジド、メピコートクロリド、酸化型グルタチオン、パクロブトラゾール、ペンディメタリン、プロヘキサジオンカルシウム、プロヒドロジャスモン、ピラフルフェンエチル、シントフェン、１－ナフタレン酢酸ナトリウム、シアン酸ナトリウム、ストレプトマイシン、チジアズロン、トリアペンテノール、トリブフォス、トリネキサパックエチル、ウニコナゾールＰ、１－ナフチルアセトアミド。 Specific examples of plant growth regulators that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
1-Methylcyclopropene, 2,3,5-triiodobenzoic acid, IAA, IBA, MCPA, MCPB, 4-CPA, 5-aminolevphosphate, 6-benzylaminopurine, absicic acid, abigricin hydrochloride, ansimi Dole, butoralin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, chlormecoat chloride, chloroprofem, choline chloride, cloprop, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop , Dikeglack, dimethipin, diquat, etephone, ethiclocate, flumethrolin, fluluprimidol, holchlorphenurone, dibererin A, dibererin A3, himexazole, inabenfide, isoprothiolan, kinetin, maleic acid hydrazide, mefluidide, mepicot chloride Paclobutrazole, pendimethalin, prohexadione calcium, prohydrojasmon, pyraflufenethyl, syntophen, sodium 1-naphthalene acetate, sodium cyanate, streptomycin, tidiazulone, triapentenol, tribphos, trinexapacethyl, Uniconazole P, 1-naphthylacetamide.
〔外部寄生虫防除もしくは駆除剤〕
　本発明の外部寄生虫防除もしくは駆除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の外部寄生虫防除もしくは駆除剤は、人獣に害を及ぼす外部寄生虫の防除効果に優れている。 [Pest control or extermination agent]
The ectoparasite control or extermination agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The ectoparasite control or extermination agent of the present invention is excellent in the effect of controlling ectoparasites that are harmful to humans and animals.
　外部寄生虫は、宿主動物、特には温血動物や魚類の体内および皮膚に寄生する。詳しくは、宿主動物の背、脇下、下腹部、内股部などに寄生して動物から血液やフケなどの栄養源を得て生息する。外部寄生虫としては、ダニ類、シラミ類、ノミ類、カ、サシバエ、ニクバエ、ウオジラミなどが挙げられる。
　本発明の外部寄生虫防除もしくは駆除剤の処理の対象となる宿主動物としては、イヌ、ネコなどの愛玩動物；愛玩鳥；ウシ、ウマ、ブタ、ヒツジなどの家畜；家禽；などの温血動物が挙げられる。その他に、サケ、マス、フグ、コイ、金魚などの魚類；ミツバチ、クワガタムシ、カブトムシなどの昆虫類；が挙げられる。
　外部寄生虫は、宿主動物、特には温血動物の中および上に寄生する。詳しくは、宿主動物の背、脇下、下腹部、内股部などに寄生して動物から血液やフケなどの栄養源を得て生息する。 Ectoparasites parasitize the body and skin of host animals, especially warm-blooded animals and fish. Specifically, it parasitizes the back, armpits, lower abdomen, inner thigh, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, flesh flies, and worms.
The host animals to be treated with the ectoparasite control or extermination agent of the present invention include pet animals such as dogs and cats; pet birds; livestock such as cows, horses, pigs and sheep; warm-blooded animals such as poultry; Can be mentioned. Other examples include fish such as salmon, trout, blowfish, carp and goldfish; insects such as honeybees, stag beetles and beetles;
Ectoparasites parasitize in and on host animals, especially warm-blooded animals. Specifically, it parasitizes the back, armpits, lower abdomen, inner thigh, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal.
　本発明の外部寄生虫防除もしくは駆除剤は、公知の獣医学的な手法（局所、経口、非経口または皮下投与）で施用することができる。その方法として、錠剤、カプセル、飼料混入などにより動物に経口的に投与する方法；　浸漬液、坐薬、注射（筋肉内、皮下、静脈内、腹腔内など）などにより動物に投与する方法；　油性または水性液剤を噴霧、ポアオン、スポットオンなどにより局所的に投与する方法；　樹脂に外部寄生虫防除剤を練り込み、前記混練物を首輪、耳札などの適当な形状に成形し、それを動物に装着し局所的に投与する方法；　などが挙げられる。 The ectoparasite control or extermination agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration). As the method, a method of orally administering to an animal by mixing tablets, capsules, feed, etc .; a method of administering to an animal by an immersion liquid, a suppository, an injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oily or A method of locally administering an aqueous solution by spraying, pore-on, spot-on, etc .; Kneading an ectoparasite control agent into a resin, molding the kneaded product into an appropriate shape such as a collar, ear tag, etc. A method of wearing and locally administering;
　本発明の外部寄生虫防除もしくは駆除剤によって防除もしくは駆除可能な外部寄生虫の具体例を以下に示す。 Specific examples of ectoparasites that can be controlled or exterminated by the ectoparasite control or extermination agent of the present invention are shown below.
（１）ダニ類（Acari）
　ワクモ科（Dermanyssidae）のダニ、オオサシダニ科（Macronyssidae）のダニ、トゲダニ科（Laelapidae）のダニ、ヘギダニ科（Varroidae）のダニ、ヒメダニ科（Argasidae）のダニ、マダニ科（Ixodidae）のダニ、キュウセンヒゼンダニ科（Psoroptidae）のダニ、ヒゼンダニ科（Sarcoptidae）のダニ、トリヒゼンダニ科(Knemidokoptidae)のダニ、ニキビダニ科（Demodixidae）のダニ、ツツガムシ科（Trombiculidae）のダニ、クワガタナカセ類などの昆虫寄生性のダニ。
（２）シラミ目（Phthiraptera）
　ケモノジラミ科（Haematopinidae）のシラミ、ケモノホソジラミ科（Linognathidae）のシラミ、タンカクハジラミ科（Menoponidae）のハジラミ、チョウカクハジラミ科（Philopteridae）のハジラミ、ケモノハジラミ科（Trichodectidae）のハジラミ。
（３）ノミ目（Siphonaptera）
　ヒトノミ科（Pulicidae）のノミ、例えば、イヌノミ属種（Ctenocephalides spp.）の、イヌノミ（Ctenocephalides canis）、ネコノミ（Ctenocephalides felis）；
スナノミ科（Tungidae）のノミ、ナガノミ科（Ceratophyllidae）のノミ、ホソノミ科（Leptopsyllidae）のノミ。
（４）カメムシ目（Hemiptera）
（５）ハエ目（Diptera）の害虫
　カ科（Culicidae）のカ、ブユ科（Simuliidae）のブユ、ヌカカ科（Ceratopogonidae）のヌカカ、アブ科（Tabanidae）のアブ、イエバエ科（Muscidae）のハエ、ツエツエバエ科（Glossinidae）のシェシェバエ、ニクバエ科のニクバエ、シラミバエ科（Hippoboscidae）のハエ、クロバエ科（Calliphoridae）のハエ、ヒツジバエ科（Oestridae）のハエ。 (1) Mites (Acari)
Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodidae mites, cucumber mites Insect-parasitic mites such as Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodixidae Demodixidae mites, Trombiculidae mites, and mulberry mites. ..
(2) Lice (Phthiraptera)
Lice of the family Haematopinidae, lice of the family Linognathidae, mallophaga of the family Menoponidae, mallophaga of the family Philopteridae, mallophaga of the family Mammal chewing (Trichodectida).
(3) Flea eyes (Siphonaptera)
Human flea (Pulicidae) fleas, such as dog fleas (Ctenocephalides spp.), Dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis);
Fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae (Leptopsyllidae).
(4) Hemiptera
(5) Diptera mosquitoes, Culicidae mosquitoes, Simuliidae mosquitoes, Ceratopogonidae mosquitoes, Tabanidae mosquitoes, Muscidae flies, Glossinidae Glossinidae, Glossinidae flies, Hipboscidae flies, Calliphoridae flies, Oestridae flies.
〔その他の有害生物についての防除剤〕
　その他にも、毒針や毒液を持ち、人獣に被害を加える害虫、各種の病原体・病原菌を媒介する害虫、人に不快感を与える害虫（有毒害虫・衛生害虫・不快害虫など）の防除効果に優れている。
　以下に、その具体例を示す。
（１）ハチ目（Hymenoptera）の害虫
　ミフシババチ科（Argidae）のハチ、タマバチ科（Cynipidae）のハチ、マツハバチ科（Diprionidae）のハチ、アリ科（Formicidae）のアリ、アリバチ科（Mutillidae ）のハチ、スズメバチ科（Vespidae）のハチ。
（２）その他の害虫
　ゴキブリ類（Blattodea）、シロアリ類（termite）、クモ類（Araneae）、ムカデ類（cetipede）、ヤスデ類（millipede）、甲殻類（crustacea）、南京虫（Cimex lectularius）。 [Control agents for other pests]
In addition, the control effect of pests that have poisonous needles and toxic liquids and damage humans, pests that transmit various pathogens and germs, and pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests, etc.) Is excellent.
A specific example is shown below.
(1) Hymenoptera pests Hymenoptera bees, Gall wasps, Gall wasps, Diprionidae ants, Formicidae ants, Mutillidae bees, A bee of the family Vespidae.
(2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), mucades (cetipede), millipedes (millipede), shellfish (crustacea), Nanjing insects (Cimex lectularius).
〔製剤処方〕
　本発明の有害生物防除剤、殺虫剤、殺ダニ剤、および外部寄生虫防除若しくは駆除剤の製剤実施例を若干示す。但し、本発明は、これら製剤実施例に限定されない。製剤実施例中の「部」および「％」は質量基準である。 [Pharmaceutical prescription]
Some examples of the preparations of the pest control agent, the insecticide, the acaricide, and the ectoparasite control or control agent of the present invention are shown. However, the present invention is not limited to these pharmaceutical examples. The "parts" and "%" in the pharmaceutical examples are based on mass.
　以下に農園芸用および水稲用の製剤処方を示す。 The following are the pharmaceutical formulations for agriculture and horticulture and paddy rice.
（製剤例１：水和剤）
　本発明化合物４０部、珪藻土５３部、高級アルコール硫酸エステル４部、およびアルキルナフタレンスルホン酸塩３部を均一に混合して微細に粉砕して、有効成分４０％の水和剤を得る。 (Formation example 1: wettable powder)
40 parts of the compound of the present invention, 53 parts of diatomaceous soil, 4 parts of higher alcohol sulfate ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder having 40% of the active ingredient.
（製剤例２：乳剤）
　本発明化合物３０部、キシレン３３部、ジメチルホルムアミド３０部、およびポリオキシエチレンアルキルアリルエーテル７部を混合し溶解させて、有効成分３０％の乳剤を得る。 (Formation example 2: emulsion)
30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.
（製剤例３：粒剤）
　本発明化合物５部、タルク４０部、クレー３８部、ベントナイト１０部、およびアルキル硫酸ソーダ７部を均一に混合して微細に粉砕し、その後、直径０．５～１．０ｍｍの粒状に造粒して、有効成分５％の粒剤を得る。 (Pharmaceutical example 3: Granules)
5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated into granules having a diameter of 0.5 to 1.0 mm. Then, a granule having 5% of the active ingredient is obtained.
（製剤例４：粒剤）
　本発明化合物５部、クレー７３部、ベントナイト２０部、ジオクチルスルホサクシネートナトリウム塩１部、およびリン酸カリウム１部を混合し粉砕し、それに水を加えてよく練り合せ、その後、造粒乾燥して、有効成分５％の粒剤を得る。 (Formation example 4: granules)
5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are mixed and crushed, water is added to the mixture, and the mixture is well kneaded, and then granulated and dried. To obtain granules having 5% of the active ingredient.
（製剤例５：懸濁剤）
　本発明化合物１０部、ポリオキシエチレンアルキルアリルエーテル４部、ポリカルボン酸ナトリウム塩２部、グリセリン１０部、キサンタンガム０．２部、および水７３．８部を混合し、３μｍ以下の粒度になるまで湿式粉砕し、有効成分１０％の懸濁剤を得る。 (Formation Example 5: Suspension)
Mix 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water until the particle size becomes 3 μm or less. Wet grind to obtain a suspension of 10% active ingredient.
　以下に外部寄生虫防除剤の製剤処方を示す。 The formulation of the ectoparasite control agent is shown below.
（製剤例６：顆粒剤）
　本発明化合物５部を有機溶媒に溶解させて溶液を得、前記の溶液をカオリン９４部およびホワイトカーボン１部の上に噴霧し、次いで溶媒を減圧下蒸発させて顆粒剤を得る。この種の顆粒剤は動物の餌に混ぜ合わせて使用することができる。 (Formation example 6: Granules)
Five parts of the compound of the present invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure to obtain granules. This type of granule can be used by mixing with animal food.
（製剤例７：注入剤）
　本発明化合物０．１～１部とラッカセイ油９９～９９．９部を均一に混合し、次いで滅菌フィルターによりろ過滅菌するにより注入剤を得る。 (Formation example 7: Injectable agent)
An injection is obtained by uniformly mixing 0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil, and then filtering and sterilizing with a sterilization filter.
（製剤例８：ポアオン剤）
　本発明化合物５部、ミリスチン酸エステル１０部、およびイソプロパノール８５部を均一に混合してポアオン剤を得る。 (Formation example 8: Poaon agent)
A poreon agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.
（製剤例９：スポットオン剤）
　本発明化合物１０～１５部、パルミチン酸エステル１０部、およびイソプロパノール７５～８０部を均一に混合してスポットオン剤を得る。 (Formation example 9: Spot-on agent)
10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on agent.
（製剤例１０：スプレー剤）
　本発明化合物１部、プロピレングリコール１０部、およびイソプロパノール８９部を均一に混合してスプレー剤を得る。 (Formation Example 10: Spray agent)
A spray agent is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.
（化合物合成例）
　次に、実施例を示し、本発明化合物をより具体的に説明する。ただし、本発明は以下の実施例によって何ら制限されるものではない。 (Example of compound synthesis)
Next, an example will be shown, and the compound of the present invention will be described more specifically. However, the present invention is not limited to the following examples.
（実施例１）
　４－（４－（５－メチル－１，２，４－オキサジアゾール－３－イル）ピペリジン－１－カルボニル）－４’，５－ビス（トリフルオロメチル）－[１，１’－ビフェニル] －２－カルボニトリルの製造 (Example 1)
4- (4- (5-Methyl-1,2,4-oxadiazole-3-yl) piperidine-1-carbonyl) -4', 5-bis (trifluoromethyl)-[1,1'-biphenyl ] -Production of 2-Carbonitrile
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
　２－シアノ－４’，５－ビス（トリフルオロメチル）－[１’，１－ビフェニル]－４－カルボン酸（０．１４ｇ）をジクロロメタン（４ｍｌ）に溶解させ、これに１－（３－ジメチルアミノプロピル）－３－エチルカルボジイミド（９７ｍｇ）、１－ヒドロキシベンゾトリアゾール（６９ｍｇ）、５－メチル－３－（ピペリジン－４－イル）－１，２，４－オキサジアゾール塩酸塩（０．１０ｇ）、およびトリエチルアミン（０．２２ｍｌ）を加えて室温にて一晩撹拌した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：n-ヘキサン／酢酸エチル＝１／１）で精製し、目的化合物（０．１７ｇ）を得た。収率８７％。
1H-NMR (CDCl3,δppm) 7.68-7.85 (6H, m), 4.59-4.66 (1H, m), 3.45-3.49 (1H, m), 3.19-3.28 (3H, m), 2.58 (3H, s), 2.16-2.22 (1H, m), 1.75-2.05 (3H, m) 2-Cyano-4', 5-bis (trifluoromethyl)-[1', 1-biphenyl] -4-carboxylic acid (0.14 g) was dissolved in dichloromethane (4 ml), and 1- (3-) Didimethylaminopropyl) -3-ethylcarbodiimide (97 mg), 1-hydroxybenzotriazole (69 mg), 5-methyl-3- (piperidin-4-yl) -1,2,4-oxadiazole hydrochloride (0. 10 g) and triethylamine (0.22 ml) were added and stirred overnight at room temperature. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 1/1) to obtain the target compound (0.17 g). Yield 87%.
1 1 H-NMR (CDCl 3 , δppm) 7.68-7.85 (6H, m), 4.59-4.66 (1H, m), 3.45-3.49 (1H, m), 3.19-3.28 (3H, m), 2.58 (3H, 3H, s), 2.16-2.22 (1H, m), 1.75-2.05 (3H, m)
（参考例１）
　５－メチル－３－（ピペリジン－４－イル）－１，２，４－オキサジアゾール塩酸塩の合成 (Reference example 1)
Synthesis of 5-methyl-3- (piperidine-4-yl) -1,2,4-oxadiazole hydrochloride
（工程１）
　ターシャリーブチル４－（Ｎ－ヒドロキシアミジン）ピペリジン－１－カルボキシレートの合成 (Step 1)
Synthesis of tertiary butyl 4- (N-hydroxyamidine) piperidine-1-carboxylate
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
　ヒドロキシアミン塩酸塩（５．０ｇ）を水（２４ｍｌ）に溶解させ、これに炭酸ナトリウム（１２．６ｇ）を加え、次いでメタノール（２４ｍｌ）とターシャリーブチル４－シアノピペリジン－１－カルボキシレート（５．０ｇ）を加えて、３．５時間加熱還流した。溶媒を減圧留去し、酢酸エチルで抽出、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、目的化合物（５．５１ｇ）を得た。収率９５％。
1H-NMR (CD3OD,δppm) 4.11 (2H, d), 2.71-2.80 (2H, m), 2.19-2.28 (1H, m), 1.72 (2H, d), 1.53-1.62 (2H, m), 1.45 (9H, s) Hydroxylamine hydrochloride (5.0 g) is dissolved in water (24 ml), sodium carbonate (12.6 g) is added thereto, then methanol (24 ml) and tertiary butyl 4-cyanopiperidine-1-carboxylate (5). (0.0 g) was added, and the mixture was heated under reflux for 3.5 hours. The solvent was evaporated under reduced pressure, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the target compound (5.51 g). Yield 95%.
1 1 H-NMR (CD 3 OD, δppm) 4.11 (2H, d), 2.71-2.80 (2H, m), 2.19-2.28 (1H, m), 1.72 (2H, d), 1.53-1.62 (2H, m) ), 1.45 (9H, s)
（工程２）
　ターシャリーブチル４－（５－メチル－１，２，４－オキサジアゾール－３－イル）ピペリジン－１－カルボキシレートの合成 (Step 2)
Synthesis of tertiary butyl 4- (5-methyl-1,2,4-oxadiazole-3-yl) piperidine-1-carboxylate
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
　ターシャリーブチル４－（Ｎ－ヒドロキシアミジン）ピペリジン－１－カルボキシレート（５．０ｇ）をＮ，Ｎ－ジメチルホルムアミド（７０ｍｌ）に溶解させ、これに無水酢酸（２．９ｍｌ）を加えて、室温にて１時間撹拌し、その後１００℃で２．５時間撹拌した。得られた液を室温まで冷却し、水に注加、酢酸エチルで抽出、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：n-ヘキサン／酢酸エチル＝１／１）で精製し、目的化合物（４．０８ｇ）を得た。収率７４％。
1H-NMR (CDCl3,δppm) 4.10-4.17 (2H, m), 2.87-2.97 (3H, m), 2.58 (3H, s), 1.96 (2H, d), 1.70-1.80 (2H, m), 1.47 (9H, s) Tersually butyl 4- (N-hydroxyamidine) piperidine-1-carboxylate (5.0 g) is dissolved in N, N-dimethylformamide (70 ml), acetic anhydride (2.9 ml) is added thereto, and room temperature is reached. Was stirred for 1 hour, and then stirred at 100 ° C. for 2.5 hours. The obtained liquid was cooled to room temperature, poured into water, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 1/1) to obtain the target compound (4.08 g). Yield 74%.
1 1 H-NMR (CDCl 3 , δppm) 4.10-4.17 (2H, m), 2.87-2.97 (3H, m), 2.58 (3H, s), 1.96 (2H, d), 1.70-1.80 (2H, m) , 1.47 (9H, s)
（工程３）
　５－メチル－３－（ピペリジン－４－イル）－１，２，４－オキサジアゾール塩酸塩の合成 (Step 3)
Synthesis of 5-methyl-3- (piperidine-4-yl) -1,2,4-oxadiazole hydrochloride
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
　ターシャリーブチル４－（５－メチル－１，２，４－オキサジアゾール－３－イル）ピペリジン－１－カルボキシレート（４．０８ｇ）を１，４－ジオキサン（３８ｍｌ）に溶解させ、４Ｍ塩酸１，４－ジオキサン溶液（１９ｍｌ）を加えて、室温にて一晩撹拌した。溶媒を減圧留去し、目的化合物（２．１５ｇ）を得た。収率８４％。
1H-NMR (CDCl3,δppm) 3.41-3.46 (2H, m), 3.11-3.17 (3H, m), 2.58 (3H, s), 2.20-2.40 (4H, m) Tershally butyl 4- (5-methyl-1,2,4-oxadiazole-3-yl) piperidine-1-carboxylate (4.08 g) is dissolved in 1,4-dioxane (38 ml) and 4M hydrochloric acid. A 1,4-dioxane solution (19 ml) was added and the mixture was stirred overnight at room temperature. The solvent was distilled off under reduced pressure to obtain the target compound (2.15 g). Yield 84%.
1 1 H-NMR (CDCl 3 , δppm) 3.41-3.46 (2H, m), 3.11-3.17 (3H, m), 2.58 (3H, s), 2.20-2.40 (4H, m)
（参考例２）
　２－シアノ－４’，５－ビス（トリフルオロメチル）－[１’，１－ビフェニル]－４－カルボン酸の合成 (Reference example 2)
Synthesis of 2-cyano-4', 5-bis (trifluoromethyl)-[1', 1-biphenyl] -4-carboxylic acid
（工程１）
　メチル４－アミノ－２－（トリフルオロメチル）ベンゾエートの合成 (Step 1)
Synthesis of methyl 4-amino-2- (trifluoromethyl) benzoate
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
　４－アミノ－２－（トリフルオロメチル）安息香酸（２５．３ｇ）をメタノール（１８０ｍｌ）に溶解させ、これに、氷冷下で塩化チオニル（１７．６ｍｌ）を加えた。その後、加熱還流下一晩撹拌した。溶媒を減圧留去し、飽和重曹水を注加、酢酸エチルで抽出、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、目的化合物（２５．２ｇ）を得た。収率９３％。
1H-NMR (CD3OD,δppm) 7.75 (1H, d), 6.97 (1H, d), 6.75 (1H, dd), 4.08-4.16 (2H, br), 3.86 (3H, s) 4-Amino-2- (trifluoromethyl) benzoic acid (25.3 g) was dissolved in methanol (180 ml), to which thionyl chloride (17.6 ml) was added under ice-cooling. Then, the mixture was stirred overnight under heating under reflux. The solvent was evaporated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added, the mixture was extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the target compound (25.2 g). Yield 93%.
1 1 H-NMR (CD 3 OD, δppm) 7.75 (1H, d), 6.97 (1H, d), 6.75 (1H, dd), 4.08-4.16 (2H, br), 3.86 (3H, s)
（工程２）
メチル４－アミノ－５－ヨード－２－（トリフルオロメチル）ベンゾエートの合成 (Step 2)
Synthesis of Methyl 4-amino-5-iodo-2- (trifluoromethyl) benzoate
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
　メチル４－アミノ－２－（トリフルオロメチル）ベンゾエート（２５．２ｇ）を酢酸（２３０ｍｌ）に溶解させ、これにＮ－ヨードスクシンイミド（２５．９ｇ）を加えて、室温にて２時間撹拌した。得られた液に水を注加し、析出物を水で洗浄した。その後、減圧乾燥させて、目的化合物（３７．１ｇ）を得た。収率９３％。
1H-NMR (CD3OD, δppm) 8.24 (1H, s), 7.00 (1H, s), 4.65 (2H, s), 3.86 (3H, s) Methyl 4-amino-2- (trifluoromethyl) benzoate (25.2 g) was dissolved in acetic acid (230 ml), N-iodosuccinimide (25.9 g) was added thereto, and the mixture was stirred at room temperature for 2 hours. Water was poured into the obtained liquid, and the precipitate was washed with water. Then, it was dried under reduced pressure to obtain the target compound (37.1 g). Yield 93%.
1 1 H-NMR (CD 3 OD, δppm) 8.24 (1H, s), 7.00 (1H, s), 4.65 (2H, s), 3.86 (3H, s)
（工程３）
　メチル４－アミノ－５－シアノ－２－（トリフルオロメチル）ベンゾエートの合成 (Step 3)
Synthesis of methyl 4-amino-5-cyano-2- (trifluoromethyl) benzoate
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
　メチル４－アミノ－５－ヨード－２－（トリフルオロメチル）ベンゾエート（３７．１ｇ）をＮＭＰ（２１０ｍｌ）に溶解させ、これにシアン化銅(I)（１１．６ｇ）を加えて、１２０℃で３時間撹拌した。得られた液を室温まで冷却し、水を注加、析出物を水で洗浄した。その後、減圧乾燥させて、目的化合物（２３．５ｇ）を得た。収率８９％。
1H-NMR (CD3OD, δppm) 8.05 (1H, s), 7.10 (1H, s), 5.02 (2H, s), 3.88 (3H, s) Methyl 4-amino-5-iodo-2- (trifluoromethyl) benzoate (37.1 g) was dissolved in NMP (210 ml), and copper (I) cyanide (11.6 g) was added thereto at 120 ° C. Was stirred for 3 hours. The obtained liquid was cooled to room temperature, water was poured, and the precipitate was washed with water. Then, it was dried under reduced pressure to obtain the target compound (23.5 g). Yield 89%.
1 1 H-NMR (CD 3 OD, δppm) 8.05 (1H, s), 7.10 (1H, s), 5.02 (2H, s), 3.88 (3H, s)
（工程４）
　メチル４－ブロモ－５－シアノ－２－（トリフルオロメチル）ベンゾエートの合成 (Step 4)
Synthesis of methyl 4-bromo-5-cyano-2- (trifluoromethyl) benzoate
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
　メチル４－アミノ－５－シアノ－２－（トリフルオロメチル）ベンゾエート（５．０ｇ）を臭化水素酸（６８ｍｌ）に溶解させ、これに、氷冷下で、水（１４ｍｌ）と亜硝酸ナトリウム（４．２ｇ）を加えて、１時間撹拌した。次いで、これに、水（６８ｍｌ）と臭化銅(I)（８．８ｇ）を加えて、室温にて一晩撹拌した。得られた液にアンモニア水を注加し、酢酸エチルで抽出、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、析出した結晶をヘキサンで洗浄し、目的化合物（４．３４ｇ）を得た。収率６９％。
1H-NMR (CD3OD, δppm) 8.10 (1H, s), 8.07 (1H, s), 3.96 (3H, s) Methyl 4-amino-5-cyano-2- (trifluoromethyl) benzoate (5.0 g) was dissolved in hydrobromic acid (68 ml), which was then ice-cooled with water (14 ml) and sodium nitrite. (4.2 g) was added, and the mixture was stirred for 1 hour. Then, water (68 ml) and copper (I) bromide (8.8 g) were added thereto, and the mixture was stirred overnight at room temperature. Ammonia water was poured into the obtained liquid, extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the precipitated crystals were washed with hexane to obtain the target compound (4.34 g). Yield 69%.
1 1 H-NMR (CD 3 OD, δppm) 8.10 (1H, s), 8.07 (1H, s), 3.96 (3H, s)
（工程５）
　メチル２－シアノ－４’，５－ビス（トリフルオロメチル）－[１’，１－ビフェニル]－４－カルボキシレートの合成 (Step 5)
Synthesis of Methyl 2-cyano-4', 5-bis (trifluoromethyl)-[1', 1-biphenyl] -4-carboxylate
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
　メチル４－ブロモ－５－シアノ－２－（トリフルオロメチル）ベンゾエート（２．７９ｇ）および４－トリフルオロメチルフェニルボロン酸（２．５８ｇ）をトルエン（３０ｍｌ）および水（３ｍｌ）の混合溶媒に溶解させ、これに炭酸カリウム（３．７ｇ）およびジクロロビス［ジ－ｔ－ブチル（ｐ－ジメチルアミノフェニル）ホスフィノ］パラジウム(II)（０．３２ｇ）を加え、窒素雰囲気下、一晩加熱還流した。得られた液を室温まで冷却し、水を注加、酢酸エチルで抽出、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：n-ヘキサン／酢酸エチル＝１０／１）で精製し、目的化合物（２．５８ｇ）を得た。収率７６％。
1H-NMR (CD3OD, δppm) 8.25 (1H, s), 7.90 (1H, s), 7.81 (2H, d), 7.71 (2H, d), 4.00 (3H, s) Methyl 4-bromo-5-cyano-2- (trifluoromethyl) benzoate (2.79 g) and 4-trifluoromethylphenylboronic acid (2.58 g) in a mixed solvent of toluene (30 ml) and water (3 ml). It was dissolved, potassium carbonate (3.7 g) and dichlorobis [di-t-butyl (p-dimethylaminophenyl) phosphino] palladium (II) (0.32 g) were added thereto, and the mixture was heated under reflux overnight under a nitrogen atmosphere. .. The obtained liquid was cooled to room temperature, water was added, the mixture was extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 10/1) to obtain the target compound (2.58 g). Yield 76%.
1 1 H-NMR (CD 3 OD, δppm) 8.25 (1H, s), 7.90 (1H, s), 7.81 (2H, d), 7.71 (2H, d), 4.00 (3H, s)
（工程６）
２－シアノ－４’，５－ビス（トリフルオロメチル）－[１’，１－ビフェニル]－４－カルボン酸の合成 (Step 6)
Synthesis of 2-cyano-4', 5-bis (trifluoromethyl)-[1', 1-biphenyl] -4-carboxylic acid
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
　メチル２－シアノ－４’，５－ビス（トリフルオロメチル）－[１’，１－ビフェニル]－４－カルボキシレート（２．５８ｇ）をメタノール（１２ｍｌ）、テトラヒドロフラン（１２ｍｌ）および水（２３ｍｌ）の混合溶媒に溶解させ、これに水酸化ナトリウム（０．４１ｇ）を加え、室温で４時間撹拌した。得られた液に希塩酸を注加、酢酸エチルで抽出、飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、目的化合物（２．４８ｇ）を得た。収率９８％。
1H-NMR (CD3OD, δppm) 8.42 (1H, s), 7.97 (1H, s), 7.83 (2H, d), 7.73 (2H, d) Methyl 2-cyano-4', 5-bis (trifluoromethyl)-[1', 1-biphenyl] -4-carboxylate (2.58 g) in methanol (12 ml), tetrahydrofuran (12 ml) and water (23 ml) Sodium hydroxide (0.41 g) was added thereto, and the mixture was stirred at room temperature for 4 hours. Dilute hydrochloric acid was added to the obtained liquid, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the target compound (2.48 g). Yield 98%.
1 1 H-NMR (CD 3 OD, δppm) 8.42 (1H, s), 7.97 (1H, s), 7.83 (2H, d), 7.73 (2H, d)
　前記の実施例と同様の方法で製造した本発明化合物の一部を第１表、第２表および第３表に示す。第１表は、式（I-1）中のＹ、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｘ2および（Ｘ3）nの組み合わせと、その組合せによって表される化合物の物性を示す。第２表は、式（I-2）中のＹ’、Ｒ1、Ｒ2、Ｒ3、Ｒ4および（Ｘ3）nの組み合わせと、その組合せによって表される化合物の物性を示す。第３表は、式（I-3）中のＹ、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｘ2およびＡｒ'の組み合わせと、その組合せによって表される化合物の物性を示す。式（I-1）および（I-2）中のｎはフェニル基上の置換基Ｘ3の数を示す。物性の欄には、融点（m.p.）または性状を示す。表中、Ｐｈはフェニル基を、Ｍｅはメチル基を、Ｅｔはエチル基をそれぞれ示す。 A part of the compound of the present invention produced by the same method as in the above Examples is shown in Tables 1, 2 and 3. Table 1 shows the combinations of Y, R 1 , R 2 , R 3 , R 4 , X 2 and (X 3 ) n in the formula (I-1) and the physical characteristics of the compounds represented by the combinations. .. Table 2 shows the combinations of Y', R 1 , R 2 , R 3 , R 4 and (X 3 ) n in the formula (I-2) and the physical characteristics of the compounds represented by the combinations. Table 3 shows the combinations of Y, R 1 , R 2 , R 3 , R 4 , X 2 and Ar'in the formula (I-3) and the physical characteristics of the compounds represented by the combinations. N in formulas (I-1) and (I-2) indicates the number of substituents X 3 on the phenyl group. In the column of physical characteristics, the melting point (mp) or the property is shown. In the table, Ph indicates a phenyl group, Me indicates a methyl group, and Et indicates an ethyl group.
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034
　表に示した化合物のうち、粘性オイルまたはアモルファスの物性の化合物については1H-NMR (CDCl3)を測定した。その測定値を以下に示す。
　化合物番号(a-8)：1H-NMR (400 MHz, CDCl3) δ ppm：1.15-1.34 (m, 5H), 1.76-2.05 (m, 3H), 2.46-2.58 (m, 4H), 2.83 (t, 1H), 3.07 (t, 1H), 3.36-3.45 (m, 1H), 4.78 (t, 1H), 6.61 (t, 1H), 7.25-7.31 (m, 2H), 7.52-7.61 (m, 2H), 7.71 (d, 1H), 7.82 (d, 1H).
　化合物番号(a-10)：1H-NMR (400 MHz, CDCl3) δ ppm：1.13-1.34 (m, 5H), 1.74-2.05 (m, 3H), 2.41-2.58 (m, 7H), 2.81 (q, 1H), 3.07 (q, 1H), 3.50 (d, 1H), 4.80 (d, 1H), 7.38 (s, 1H), 7.59 (d, 1H), 7.65-7.67 (m, 2H), 7.76-7.78 (d, 2H).
　化合物番号(a-18)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.82 (d, 1H), 7.80 (dd, 2H), 7.67 (dd, 2H), 7.29 (s, 1H), 4.75 (d, 1H), 3.54 (d, 1H), 3.12-3.20 (m, 1H), 2.81 (t, 1H), 2.43-2.57 (m, 4H), 1.70-2.02 (m, 3H), 1.15-1.36 (m, 5H).
　化合物番号(a-19)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.82 (d, 1H), 7.80 (dd, 2H), 7.67 (dd, 2H), 7.29 (s, 1H), 4.77 (d, 1H), 3.55 (d, 1H), 3.10-3.26 (m, 1H), 2.68-2.92 (m, 4H), 1.80-2.45 (m, 4H), 1.30-1.51 (m, 5H).
　化合物番号(a-20)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.82 (d, 1H), 7.80 (dd, 2H), 7.67 (dd, 2H), 7.29 (s, 1H), 4.77 (d, 1H), 3.55 (d, 1H), 2.85-3.30 (m, 6H), 2.39-2.51 (m, 1H), 2.00-2.15 (m, 2H), 1.38-1.52 (m, 5H).
　化合物番号(a-32)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.55 ( d, 2H), 7.65-7.78 (m, 6H), 4.70-4.82 (m, 1H), 3.00-3.59 (m, 4H), 1.80-2.22 (m, 4H).
　化合物番号(a-38)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.78 ( d, 2H), 7.68-7.64 (m, 3H), 6.98 (d, 1H), 4.83-4.80 (m, 1H), 3.95 (s, 3H), 3.53-3.50 (m, 1H), 3.18-3.05 (m, 1H), 2.90-2.68 (m, 4H), 2.50-1.75 (m, 4H), 1.55-1.30 (m, 5H).
　化合物番号(a-39)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.78 ( d, 2H), 7.68-7.64 (m, 3H), 6.98 (s, 1H), 4.80-4.77 (m, 1H), 3.95-3.94 (m, 3H), 3.51-3.48 (m, 1H), 3.19-2.84 (m, 6H), 2.43 (brs, 1H), 2.11-2.03 (m, 2H), 1.54-1.30 (m, 5H).
　化合物番号(a-40)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.56 (s, 2H), 7.78 (d, 2H), 7.71-7.67 (m, 3H), 6.99 (s, 1H), 4.85-4.82 (m, 1H), 3.96 (s, 3H), 3.63-3.59 (m, 1H), 3.27-3.15 (m, 2H), 3.05-2.99 (m, 1H), 2.20-1.78 (m, 4H).
　化合物番号(a-41)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.77 (s, 1H), 7.69 (d, 1H), 7.40 (dd, 2H), 7.26 (s, 1H), 4.61 (t, 1H), 3.89 (s, 3H), 3.42-3.55 (m, 1H), 3.00-3.27 (m, 3H), 2.57 (s, 3H), 1.75-2.21 (m, 4H).
　化合物番号(a-42)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.81 (s, 1H), 7.70 (d, 1H), 7.40 (dd, 1H), 7.34 (dd, 1H), 7.25 (s, 1H), 4.61 (t, 1H), 4.14 (q, 2H), 3.42-3.55 (m, 1H), 3.00-3.27 (m, 3H), 2.57 (s, 3H), 1.75-2.21 (m, 4H), 1.39 (t, 3H).
　化合物番号(a-44)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.80 (s, 1H), 7.69 (d, 1H), 7.40 (dd, 1H), 7.35 (dd, 1H), 7.21 (s, 1H), 4.80 (t, 1H), 4.14 (q, 2H), 2.65-3.50 (m, 7H), 1.71-2.49 (m, 5H), 1.16-1.52 (m, 7H).
　化合物番号(a-45)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.80 (s, 1H), 7.69 (d, 1H), 7.40 (dd, 1H), 7.35 (dd, 1H), 7.21 (s, 1H), 4.78 (t, 1H), 4.14 (q, 2H), 2.81-3.49 (m, 8H), 2.38-2.41 (m, 1H), 2.00-2.15 (m, 2H), 1.17-1.51 (m, 7H).
　化合物番号(a-46)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.55 (d, 2H), 7.78 (s, 1H), 7.75 (d, 1H), 7.37 (dd, 2H), 7.25 (s, 1H), 4.80 (t, 1H), 3.90 (s, 3H), 3.00-3.54 (m, 4H), 1.80-2.25 (m, 4H)
　化合物番号(a-47)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.55 (d, 2H), 7.80 (s, 1H), 7.74 (d, 1H), 7.39 (dd, 1H), 7.33 (dd, 1H) , 7.23 (s, 1H), 4.79 (t, 1H), 4.15 (q, 2H), 3.00-3.52 (m, 4H), 1.80-2.22 (m, 4H), 1.38 (t, 3H).
　化合物番号(a-48)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.76 (s, 1H), 7.66 (d, 1H), 7.31-7.39 (m, 2H), 7.25 (s, 1H), 5.45 (br, 1H), 4.76 (t, 1H), 3.88 (s, 3H), 2.80-3.42 (m, 4H), 2.80 (d, 3H), 1.67-2.30 (m, 4H), 1.05-1.32 (m, 2H).
　化合物番号(a-49)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.79 (s, 1H), 7.67 (d, 1H), 7.38 (dd, 1H), 7.33 (dd, 1H), 7.23 (s, 1H), 5.42 (br, 1H), 4.78 (t, 1H), 4.14 (q, 2H), 2.80-3.35 (m, 4H), 2.81 (d, 3H), 1.67-2.22 (m, 4H), 1.37 (t, 3H), 1.10-1.31 (m, 2H)
　化合物番号(a-50)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.78 (d, 2H), 7.69 (s, 1H), 7.68 (d, 1H), 6.99 (s, 1H), 4.68 (dd, 1H), 3.96 (s, 3H), 3.58 (d, 1H), 3.22 (dd, 1H), 3.05-3.21 (m, 2H), 2.59 (s, 3H), 2.18 (d, 1H), 1.87-2.05 (m, 2H), 1.74-1.82 (m, 1H).
　化合物番号(a-51)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.65 (d, 1H), 7.59 (d, 2H), 7.37 (d, 2H), 6.97 (d, 1H), 3.95 (s, 3H), 3.59 (d, 1H), 3.21 (dd, 1H), 3.07-3.15 (m, 2H), 2.59 (s, 3H), 2.16 (d, 1H), 1.87-2.05 (m, 2H), 1.74-1.83 (m, 1H).
　化合物番号(a-53)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.64 (d, 1H), 7.56 (d, 2H), 7.26 (d, 2H), 6.97 (s, 1H), 6.59 (t, 1H), 4.67 (d, 1H), 3.95 (s, 3H), 3.21 (dd, 1H), 3.04-3.16 (m, 2H), 2.16 (d, 1H), 1.83-2.05 (m, 2H), 1.65-1.83 (m, 1H).
　化合物番号(a-54)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.56 (s, 2H), 7.65 (d, 1H), 7.57 (d, 2H), 7.25 (d, 2H), 6.97 (s, 1H), 6.59 (t, 1H), 4.83 (d, 1H), 3.95 (s, 3H), 3.61 (d, 1H), 3.15-3.26 (m, 2H), 2.18 (d, 1H), 1.90-2.08 (m, 2H), 1.82-(dd, 1H).
　化合物番号(a-55)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.79 (s, 1H), 7.70 (d, 1H), 7.30 (d, 1H), 6.98 (d, 1H), 6.89 (s, 1H), 4.62 (t, 1H), 3.89 (s, 3H), 3.47-3.56 (m, 1H), 3.02-3.30 (m, 3H), 2.60 (d, 3H), 1.78-2.23 (m, 4H).
　化合物番号(a-56)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.55 (d, 2H), 7.78 (s, 1H), 7.70 (d, 1H), 7.30 (d, 1H), 6.98 (d, 1H), 6.89 (s, 1H), 4.80 (t, 1H), 3.88 (s, 3H), 3.00-3.60 (m, 4H), 1.80-2.25 (m, 4H).
　化合物番号(a-58)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.76 (s, 1H), 7.67 (d, 1H), 7.30 (d, 1H), 6.95 (d, 1H), 6.88 (s, 1H), 4.80 (t, 1H), 3.87 (s, 3H), 3.05-3.52 (m, 2H), 2.66-2.93 (m, 4H), 1.77-2.50 (m, 4H), 1.25-1.55 (m, 5H).
　化合物番号(a-59)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.76 (s, 1H), 7.67 (d, 1H), 7.30 (d, 1H), 6.95 (d, 1H), 6.88 (s, 1H), 4.80 (dd, 1H), 3.87 (s, 3H), 2.84-3.50 (m, 6H), 2.40-2.52 (m, 1H), 1.99-2.16 (m, 2H), 1.29-1.55 (m, 5H).
　化合物番号(a-61)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.77 (d, 2H), 7.68 (d, 2H), 7.64 (s, 1H), 7.60 (s, 1H), 4.82-4.53 (m, 3H), 3.54 (brs, 1H), 3.44 (s, 3H), 3.11 (brs, 1H), 2.90-2.72 (m, 4H), 2.47-1.79 (m, 4H), 1.97-1.26 (m, 5H).
　化合物番号(a-62)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.77 (d, 2H), 7.68 (d, 2H), 7.63 (s, 1H), 7.59 (s, 1H), 4.78-4.53 (m, 3H), 3.53 (brs, 1H), 3.44 (s, 3H), 3.12-2.86 (m, 6H), 2.46-2.02 (m, 3H), 1.45-1.35 (m, 5H).
　化合物番号(a-63)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.56 (s, 2H), 7.77 (d, 2H), 7.70-7.65 (m, 4H), 4.86-4.57 (m, 3H), 3.67-3.64 (m, 1H), 3.48 (s, 3H), 3.26-3.00 (m, 3H), 2.21-2.18 (m, 1H), 1.97 (brs, 3H).
　化合物番号(a-66)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.77 (d, 2H), 7.69 (d, 2H), 7.66-7.62 (m, 2H), 4.63-4.54 (m, 3H), 3.64-3.61 (m, 1H), 3.47 (s, 3H), 3.29-3.08 (m, 3H), 2.59 (s, 3H), 2.47-1.83 (m, 4H).
　化合物番号(a-67)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.62 (d, 1H), 7.58 (dd, 2H), 7.35 (d, 2H), 6.96 (d, 1H), 4.81 (d, 1H), 3.95 (s, 3H), 3.45-3.53 (m, 1H), 3.01-3.17 (m, 1H), 2.90 (dt, 1H), 2.67-2.80 (m, 3H), 2,44 (dt, 1H), 2.05-2.31 (m, 2H), 1.83 (dt, 1H), 1.45 (s, 1H), 1.37 (t, 4H).
　化合物番号(a-69)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.68 (d, 1H), 7.58 (dd, 1H), 7.57 (s, 1H), 7.52 (d, 1H), 7.00 (s, 1H), 4.67 (dd, 1H), 3.94 (s, 3H), 3.58 (d, 1H), 3.22 (dd, 1H), 3.07-3.18 (m, 2H), 2.59 (s, 3H), 2.17 (d, 1H), 1.88-2.05 (m, 2H), 1.79 (dd, 1H).
　化合物番号(a-72)：1H-NMR (400 MHz, CDCl3) δ ppm： 7.62 (d, 1H), 7.38 (d, 1H), 7.34 (d, 1H), 7.24 (s, 1H), 6.93 (s, 1H), 4.68 (d, 1H), 3.91 (s, 3H), 3.90 (s, 3H), 3.60 (d, 1H), 3.22 (dd, 1H), 3.04-3.18 (m, 2H), 2.59 (s, 3H), 2.15-2.19 (m, 1H), 1.88-2.07 (m, 2H), 1.73-1.84 (dm, 1H).
　化合物番号(a-74)：1H-NMR (400 MHz, CDCl3) δ ppm： 8.55 (s, 2H), 7.63 (d, 1H), 7.36 (dd, 1H), 7.34 (d, 1H), 7.24 (s, 1H), 6.94 (s, 1H), 4.83 (d, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 3.63 (d, 1H), 3.16-3.27 (m, 2H), 2.99-3.05 (m, 1H), 2.18 (d, 1H), 1.96-2.0 (m, 1H), 1.97 (dd, 1H), 1.83 (dm, 1H).
　化合物番号(a-75)：1H-NMR (400 MHz, CDCl3) δ ppm：8.09 (s, 1H), 7.80 (d, 1H), 7.67 (d, 1H), 7.34 (s, 1H), 7.27 (d, 1H), 7.20 (d, 1H), 4.62 (t, 1H), 4.26 (q, 2H), 3.90 (s, 3H), 3.51 (t, 1H), 3.30-3.00 (m, 3H), 2.60 (d, 3H), 2.22-1.76 (m, 4H), 1.35 (t, 3H).
　化合物番号(a-76)：1H-NMR (400 MHz, CDCl3) δ ppm：8.57 (d, 2H), 8.09 (s, 1H), 7.80 (d, 1H), 7.67 (d, 1H), 7.34 (s, 1H), 7.27 (d, 1H), 7.20 (d, 1H), 4.80 (t, 1H), 4.26 (q, 2H), 3.90 (s, 3H), 3.55 (t, 1H), 3.31-3.00 (m, 3H), 2.25-1.79 (m, 4H), 1.35 (t, 3H).
　化合物番号(a-77)：1H-NMR (400 MHz, CDCl3) δ ppm：7.09 (s, 1H), 7.80 (d, 1H), 7.67 (d, 1H), 7.34 (s, 1H), 7.27 (d, 1H), 7.20 (d, 1H), 4.79 (t, 1H), 4.26 (q, 2H), 3.90 (s, 3H), 3.42 (dd, 1H), 3.12-2.77 (m, 2H), 2.57-2.40 (m, 4H), 2.02-1.68 (m, 3H), 1.35 (t, 3H), 1.34-1.12(m, 4H). Among the compounds shown in the table, 1 H-NMR (CDCl 3 ) was measured for compounds having viscous oil or amorphous physical characteristics. The measured values are shown below.
Compound No. (a-8): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 1.15-1.34 (m, 5H), 1.76-2.05 (m, 3H), 2.46-2.58 (m, 4H), 2.83 (t, 1H), 3.07 (t, 1H), 3.36-3.45 (m, 1H), 4.78 (t, 1H), 6.61 (t, 1H), 7.25-7.31 (m, 2H), 7.52-7.61 (m) , 2H), 7.71 (d, 1H), 7.82 (d, 1H).
Compound No. (a-10): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 1.13-1.34 (m, 5H), 1.74-2.05 (m, 3H), 2.41-2.58 (m, 7H), 2.81 (q, 1H), 3.07 (q, 1H), 3.50 (d, 1H), 4.80 (d, 1H), 7.38 (s, 1H), 7.59 (d, 1H), 7.65-7.67 (m, 2H), 7.76-7.78 (d, 2H).
Compound No. (a-18): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.82 (d, 1H), 7.80 (dd, 2H), 7.67 (dd, 2H), 7.29 (s, 1H), 4.75 (d, 1H), 3.54 (d, 1H), 3.12-3.20 (m, 1H), 2.81 (t, 1H), 2.43-2.57 (m, 4H), 1.70-2.02 (m, 3H), 1.15- 1.36 (m, 5H).
Compound No. (a-19): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.82 (d, 1H), 7.80 (dd, 2H), 7.67 (dd, 2H), 7.29 (s, 1H), 4.77 (d, 1H), 3.55 (d, 1H), 3.10-3.26 (m, 1H), 2.68-2.92 (m, 4H), 1.80-2.45 (m, 4H), 1.30-1.51 (m, 5H).
Compound No. (a-20): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.82 (d, 1H), 7.80 (dd, 2H), 7.67 (dd, 2H), 7.29 (s, 1H), 4.77 (d, 1H), 3.55 (d, 1H), 2.85-3.30 (m, 6H), 2.39-2.51 (m, 1H), 2.00-2.15 (m, 2H), 1.38-1.52 (m, 5H).
Compound No. (a-32): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.55 (d, 2H), 7.65-7.78 (m, 6H), 4.70-4.82 (m, 1H), 3.00-3.59 (m, 4H), 1.80-2.22 (m, 4H).
Compound No. (a-38): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.78 (d, 2H), 7.68-7.64 (m, 3H), 6.98 (d, 1H), 4.83-4.80 (m) , 1H), 3.95 (s, 3H), 3.53-3.50 (m, 1H), 3.18-3.05 (m, 1H), 2.90-2.68 (m, 4H), 2.50-1.75 (m, 4H), 1.55-1.30 (m, 5H).
Compound No. (a-39): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.78 (d, 2H), 7.68-7.64 (m, 3H), 6.98 (s, 1H), 4.80-4.77 (m) , 1H), 3.95-3.94 (m, 3H), 3.51-3.48 (m, 1H), 3.19-2.84 (m, 6H), 2.43 (brs, 1H), 2.11-2.03 (m, 2H), 1.54-1.30 (m, 5H).
Compound No. (a-40): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.56 (s, 2H), 7.78 (d, 2H), 7.71-7.67 (m, 3H), 6.99 (s, 1H) ), 4.85-4.82 (m, 1H), 3.96 (s, 3H), 3.63-3.59 (m, 1H), 3.27-3.15 (m, 2H), 3.05-2.99 (m, 1H), 2.20-1.78 (m) , 4H).
Compound No. (a-41): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.77 (s, 1H), 7.69 (d, 1H), 7.40 (dd, 2H), 7.26 (s, 1H), 4.61 (t, 1H), 3.89 (s, 3H), 3.42-3.55 (m, 1H), 3.00-3.27 (m, 3H), 2.57 (s, 3H), 1.75-2.21 (m, 4H).
Compound No. (a-42): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.81 (s, 1H), 7.70 (d, 1H), 7.40 (dd, 1H), 7.34 (dd, 1H), 7.25 (s, 1H), 4.61 (t, 1H), 4.14 (q, 2H), 3.42-3.55 (m, 1H), 3.00-3.27 (m, 3H), 2.57 (s, 3H), 1.75-2.21 ( m, 4H), 1.39 (t, 3H).
Compound No. (a-44): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.80 (s, 1H), 7.69 (d, 1H), 7.40 (dd, 1H), 7.35 (dd, 1H), 7.21 (s, 1H), 4.80 (t, 1H), 4.14 (q, 2H), 2.65-3.50 (m, 7H), 1.71-2.49 (m, 5H), 1.16-1.52 (m, 7H).
Compound No. (a-45): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.80 (s, 1H), 7.69 (d, 1H), 7.40 (dd, 1H), 7.35 (dd, 1H), 7.21 (s, 1H), 4.78 (t, 1H), 4.14 (q, 2H), 2.81-3.49 (m, 8H), 2.38-2.41 (m, 1H), 2.00-2.15 (m, 2H), 1.17- 1.51 (m, 7H).
Compound No. (a-46): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.55 (d, 2H), 7.78 (s, 1H), 7.75 (d, 1H), 7.37 (dd, 2H), 7.25 (s, 1H), 4.80 (t, 1H), 3.90 (s, 3H), 3.00-3.54 (m, 4H), 1.80-2.25 (m, 4H)
Compound No. (a-47): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.55 (d, 2H), 7.80 (s, 1H), 7.74 (d, 1H), 7.39 (dd, 1H), 7.33 (dd, 1H), 7.23 (s, 1H), 4.79 (t, 1H), 4.15 (q, 2H), 3.00-3.52 (m, 4H), 1.80-2.22 (m, 4H), 1.38 (t, 3H).
Compound No. (a-48): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.76 (s, 1H), 7.66 (d, 1H), 7.31-7.39 (m, 2H), 7.25 (s, 1H) ), 5.45 (br, 1H), 4.76 (t, 1H), 3.88 (s, 3H), 2.80-3.42 (m, 4H), 2.80 (d, 3H), 1.67-2.30 (m, 4H), 1.05- 1.32 (m, 2H).
Compound No. (a-49): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.79 (s, 1H), 7.67 (d, 1H), 7.38 (dd, 1H), 7.33 (dd, 1H), 7.23 (s, 1H), 5.42 (br, 1H), 4.78 (t, 1H), 4.14 (q, 2H), 2.80-3.35 (m, 4H), 2.81 (d, 3H), 1.67-2.22 (m, 4H), 1.37 (t, 3H), 1.10-1.31 (m, 2H)
Compound No. (a-50): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.78 (d, 2H), 7.69 (s, 1H), 7.68 (d, 1H), 6.99 (s, 1H), 4.68 (dd, 1H), 3.96 (s, 3H), 3.58 (d, 1H), 3.22 (dd, 1H), 3.05-3.21 (m, 2H), 2.59 (s, 3H), 2.18 (d, 1H) , 1.87-2.05 (m, 2H), 1.74-1.82 (m, 1H).
Compound No. (a-51): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.65 (d, 1H), 7.59 (d, 2H), 7.37 (d, 2H), 6.97 (d, 1H), 3.95 (s, 3H), 3.59 (d, 1H), 3.21 (dd, 1H), 3.07-3.15 (m, 2H), 2.59 (s, 3H), 2.16 (d, 1H), 1.87-2.05 (m, 2H), 1.74-1.83 (m, 1H).
Compound No. (a-53): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.64 (d, 1H), 7.56 (d, 2H), 7.26 (d, 2H), 6.97 (s, 1H), 6.59 (t, 1H), 4.67 (d, 1H), 3.95 (s, 3H), 3.21 (dd, 1H), 3.04-3.16 (m, 2H), 2.16 (d, 1H), 1.83-2.05 (m, 2H), 1.65-1.83 (m, 1H).
Compound No. (a-54): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.56 (s, 2H), 7.65 (d, 1H), 7.57 (d, 2H), 7.25 (d, 2H), 6.97 (s, 1H), 6.59 (t, 1H), 4.83 (d, 1H), 3.95 (s, 3H), 3.61 (d, 1H), 3.15-3.26 (m, 2H), 2.18 (d, 1H) , 1.90-2.08 (m, 2H), 1.82- (dd, 1H).
Compound No. (a-55): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.79 (s, 1H), 7.70 (d, 1H), 7.30 (d, 1H), 6.98 (d, 1H), 6.89 (s, 1H), 4.62 (t, 1H), 3.89 (s, 3H), 3.47-3.56 (m, 1H), 3.02-3.30 (m, 3H), 2.60 (d, 3H), 1.78-2.23 ( m, 4H).
Compound No. (a-56): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.55 (d, 2H), 7.78 (s, 1H), 7.70 (d, 1H), 7.30 (d, 1H), 6.98 (d, 1H), 6.89 (s, 1H), 4.80 (t, 1H), 3.88 (s, 3H), 3.00-3.60 (m, 4H), 1.80-2.25 (m, 4H).
Compound No. (a-58): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.76 (s, 1H), 7.67 (d, 1H), 7.30 (d, 1H), 6.95 (d, 1H), 6.88 (s, 1H), 4.80 (t, 1H), 3.87 (s, 3H), 3.05-3.52 (m, 2H), 2.66-2.93 (m, 4H), 1.77-2.50 (m, 4H), 1.25- 1.55 (m, 5H).
Compound No. (a-59): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.76 (s, 1H), 7.67 (d, 1H), 7.30 (d, 1H), 6.95 (d, 1H), 6.88 (s, 1H), 4.80 (dd, 1H), 3.87 (s, 3H), 2.84-3.50 (m, 6H), 2.40-2.52 (m, 1H), 1.99-2.16 (m, 2H), 1.29- 1.55 (m, 5H).
Compound No. (a-61): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.77 (d, 2H), 7.68 (d, 2H), 7.64 (s, 1H), 7.60 (s, 1H), 4.82-4.53 (m, 3H), 3.54 (brs, 1H), 3.44 (s, 3H), 3.11 (brs, 1H), 2.90-2.72 (m, 4H), 2.47-1.79 (m, 4H), 1.97- 1.26 (m, 5H).
Compound No. (a-62): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.77 (d, 2H), 7.68 (d, 2H), 7.63 (s, 1H), 7.59 (s, 1H), 4.78-4.53 (m, 3H), 3.53 (brs, 1H), 3.44 (s, 3H), 3.12-2.86 (m, 6H), 2.46-2.02 (m, 3H), 1.45-1.35 (m, 5H).
Compound No. (a-63): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.56 (s, 2H), 7.77 (d, 2H), 7.70-7.65 (m, 4H), 4.86-4.57 (m) , 3H), 3.67-3.64 (m, 1H), 3.48 (s, 3H), 3.26-3.00 (m, 3H), 2.21-2.18 (m, 1H), 1.97 (brs, 3H).
Compound No. (a-66): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.77 (d, 2H), 7.69 (d, 2H), 7.66-7.62 (m, 2H), 4.63-4.54 (m) , 3H), 3.64-3.61 (m, 1H), 3.47 (s, 3H), 3.29-3.08 (m, 3H), 2.59 (s, 3H), 2.47-1.83 (m, 4H).
Compound No. (a-67): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.62 (d, 1H), 7.58 (dd, 2H), 7.35 (d, 2H), 6.96 (d, 1H), 4.81 (d, 1H), 3.95 (s, 3H), 3.45-3.53 (m, 1H), 3.01-3.17 (m, 1H), 2.90 (dt, 1H), 2.67-2.80 (m, 3H), 2, 44 (dt, 1H), 2.05-2.31 (m, 2H), 1.83 (dt, 1H), 1.45 (s, 1H), 1.37 (t, 4H).
Compound No. (a-69): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.68 (d, 1H), 7.58 (dd, 1H), 7.57 (s, 1H), 7.52 (d, 1H), 7.00 (s, 1H), 4.67 (dd, 1H), 3.94 (s, 3H), 3.58 (d, 1H), 3.22 (dd, 1H), 3.07-3.18 (m, 2H), 2.59 (s, 3H) , 2.17 (d, 1H), 1.88-2.05 (m, 2H), 1.79 (dd, 1H).
Compound No. (a-72): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.62 (d, 1H), 7.38 (d, 1H), 7.34 (d, 1H), 7.24 (s, 1H), 6.93 (s, 1H), 4.68 (d, 1H), 3.91 (s, 3H), 3.90 (s, 3H), 3.60 (d, 1H), 3.22 (dd, 1H), 3.04-3.18 (m, 2H) , 2.59 (s, 3H), 2.15-2.19 (m, 1H), 1.88-2.07 (m, 2H), 1.73-1.84 (dm, 1H).
Compound No. (a-74): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.55 (s, 2H), 7.63 (d, 1H), 7.36 (dd, 1H), 7.34 (d, 1H), 7.24 (s, 1H), 6.94 (s, 1H), 4.83 (d, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 3.63 (d, 1H), 3.16-3.27 (m, 2H) , 2.99-3.05 (m, 1H), 2.18 (d, 1H), 1.96-2.0 (m, 1H), 1.97 (dd, 1H), 1.83 (dm, 1H).
Compound No. (a-75): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.09 (s, 1H), 7.80 (d, 1H), 7.67 (d, 1H), 7.34 (s, 1H), 7.27 (d, 1H), 7.20 (d, 1H), 4.62 (t, 1H), 4.26 (q, 2H), 3.90 (s, 3H), 3.51 (t, 1H), 3.30-3.00 (m, 3H) , 2.60 (d, 3H), 2.22-1.76 (m, 4H), 1.35 (t, 3H).
Compound No. (a-76): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 8.57 (d, 2H), 8.09 (s, 1H), 7.80 (d, 1H), 7.67 (d, 1H), 7.34 (s, 1H), 7.27 (d, 1H), 7.20 (d, 1H), 4.80 (t, 1H), 4.26 (q, 2H), 3.90 (s, 3H), 3.55 (t, 1H), 3.31 -3.00 (m, 3H), 2.25-1.79 (m, 4H), 1.35 (t, 3H).
Compound No. (a-77): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 7.09 (s, 1H), 7.80 (d, 1H), 7.67 (d, 1H), 7.34 (s, 1H), 7.27 (d, 1H), 7.20 (d, 1H), 4.79 (t, 1H), 4.26 (q, 2H), 3.90 (s, 3H), 3.42 (dd, 1H), 3.12-2.77 (m, 2H) , 2.57-2.40 (m, 4H), 2.02-1.68 (m, 3H), 1.35 (t, 3H), 1.34-1.12 (m, 4H).
　化合物番号(c-3)：1H-NMR (400 MHz, CDCl3) δ ppm：1.14-1.33 (m, 5H), 1.75-2.05 (m, 3H), 2.46-2.57 (m, 4H), 2.84 (t, 1H), 3.01-3.08 (m, 1H), 3.32-3.38 (m, 1H), 4.51 (t, 2H), 4.78 (t, 1H), 6.08 (tt, 1H), 7.43 (dd, 1H), 7.72 (d, 1H), 7.87 (d, 1H), 8.21 (d, 1H), 8.54 (d, 1H).
　化合物番号(c-14)：1H-NMR (400 MHz, CDCl3) δ ppm： 9.07 (s, 1H), 8.25 (d, 1H), 8.15 (dd, 1H), 8.00 (dd, 1H), 7.80 (dd, 1H), 4.59 (t, 1H), 3.10-3.61 (m, 3H), 2.45-2.70 (m, 5H), 1.21-1.85 (m, 7H).
　化合物番号(c-17)：1H-NMR (400 MHz, CDCl3) δ ppm： 9.07 (s, 1H), 8.56 (d, 2H), 8.25 (s, 1H), 8.15 (dd, 1H), 8.00 (d, 1H), 7.85 (dd, 1H), 4.70-4.82 (m, 1H), 3.00-3.59 (m, 4H), 1.78-2.25 (m, 4H). Compound No. (c-3): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 1.14-1.33 (m, 5H), 1.75-2.05 (m, 3H), 2.46-2.57 (m, 4H), 2.84 (t, 1H), 3.01-3.08 (m, 1H), 3.32-3.38 (m, 1H), 4.51 (t, 2H), 4.78 (t, 1H), 6.08 (tt, 1H), 7.43 (dd, 1H) ), 7.72 (d, 1H), 7.87 (d, 1H), 8.21 (d, 1H), 8.54 (d, 1H).
Compound No. (c-14): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 9.07 (s, 1H), 8.25 (d, 1H), 8.15 (dd, 1H), 8.00 (dd, 1H), 7.80 (dd, 1H), 4.59 (t, 1H), 3.10-3.61 (m, 3H), 2.45-2.70 (m, 5H), 1.21-1.85 (m, 7H).
Compound No. (c-17): 1 H-NMR (400 MHz, CDCl 3 ) δ ppm: 9.07 (s, 1H), 8.56 (d, 2H), 8.25 (s, 1H), 8.15 (dd, 1H), 8.00 (d, 1H), 7.85 (dd, 1H), 4.70-4.82 (m, 1H), 3.00-3.59 (m, 4H), 1.78-2.25 (m, 4H).
〔生物試験〕
　本発明化合物が、殺虫剤、殺ダニ剤または外部寄生虫防除剤の有効成分として有用であることを以下の試験例で示す。 [Biological test]
The following test examples show that the compound of the present invention is useful as an active ingredient of an insecticide, an acaricide or a ectoparasite control agent.
（試験用乳剤の調製）
　本発明化合物５質量部、ジメチルホルムアミド９３．６質量部、およびポリオキシエチレンアルキルアリールエーテル１．４質量部を混合し溶解させて、有効成分５％の乳剤（I）を調製した。
　また、ジメチルホルムアミド９８．６質量部およびポリオキシエチレンアルキルアリールエーテル１．４質量部を混合し溶媒対照液を調製した。 (Preparation of test emulsion)
5 parts by mass of the compound of the present invention, 93.6 parts by mass of dimethylformamide, and 1.4 parts by mass of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion (I) containing 5% of the active ingredient.
Further, 98.6 parts by mass of dimethylformamide and 1.4 parts by mass of polyoxyethylene alkylaryl ether were mixed to prepare a solvent control solution.
（試験例１）　アワヨトウに対する効力試験
　乳剤（I）を、本発明化合物の濃度が１２５質量ｐｐｍになるように水で希釈した。トウモロコシ葉片を前記希釈液に３０秒間浸漬した。このトウモロコシ葉片を、シャーレに入れ、アワヨトウ２齢幼虫５頭を放ち、乳剤処理区とした。
　同様に、溶媒対照液を、前記乳剤（I）と同率で水で希釈し、これにトウモロコシ葉片を３０秒間浸漬した。このトウモロコシ葉片を、シャーレに入れ、アワヨトウ２齢幼虫５頭を放ち、当該シャーレを溶媒対照区とした。
　前記のシャーレを、試験期間中、温度２５℃・湿度６０％の恒温室内に放置した。放虫から６日間経過したときに生死判定を行い、乳剤処理区における殺虫率を下記式に基づき算出した。同時に、乳剤処理区および溶媒対照区における摂食量を測定した。試験は２反復で行った。
　殺虫率（％）＝（死亡虫数/供試虫数）×１００ (Test Example 1) Efficacy test against armyworm Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass. The corn leaf pieces were immersed in the diluted solution for 30 seconds. The corn leaf pieces were placed in a petri dish, and 5 second-instar larvae of Mythimna separata were released to prepare an emulsion treatment group.
Similarly, the solvent control solution was diluted with water at the same rate as the emulsion (I), and the corn leaf pieces were immersed therein for 30 seconds. The corn leaf pieces were placed in a petri dish, and 5 second-instar larvae of Mythimna separata were released, and the petri dish was used as a solvent control group.
The petri dish was left in a constant temperature room at a temperature of 25 ° C. and a humidity of 60% during the test period. Life or death was determined when 6 days had passed since the release of the insects, and the insecticidal rate in the emulsion treatment group was calculated based on the following formula. At the same time, the amount of food intake in the emulsion treatment group and the solvent control group was measured. The test was performed in two iterations.
Insecticide rate (%) = (number of dead insects / number of test insects) x 100
　化合物番号a-6、a-11、a-12、a-13、a-14、a-17、a-20、a-23、a-24、a-26、a-27、a-28、a-29、a-30、a-31、a-32、a-34、a-35、a-40、a-41、a-42、a-43、a-44、a-45、a-46、a-47、a-52、a-55、a-56、a-57、a-58、a-59、a-71、a-72、a-74、a-76およびｃ-17の化合物について、アワヨトウに対する効力試験を行った。いずれの化合物もアワヨトウに対して、殺虫率が９０％または摂食量が対溶媒対照区比で１０％以下であった。 Compound numbers a-6, a-11, a-12, a-13, a-14, a-17, a-20, a-23, a-24, a-26, a-27, a-28, a-29, a-30, a-31, a-32, a-34, a-35, a-40, a-41, a-42, a-43, a-44, a-45, a- 46, a-47, a-52, a-55, a-56, a-57, a-58, a-59, a-71, a-72, a-74, a-76 and c-17 The compound was tested for efficacy against armyworm. In each compound, the insecticidal rate was 90% or the food intake was 10% or less as compared with the solvent control group with respect to the armyworm.
（試験例２）ワタアブラムシに対する効力試験
　３寸鉢にきゅうりを播種した。発芽から１０日経過したキュウリに、ワタアブラムシ雌成虫を放虫した。翌日に、産下された１齢幼虫は残し、雌成虫は除去した。乳剤（I）を、本発明化合物濃度が１２５質量ｐｐｍになるように水で希釈した。この希釈液を前記のキュウリに散布した。その後キュウリを温度２５℃・湿度６０％の恒温室内に置き、５日経過後にワタアブラムシの生死を調べ、殺虫率を求めた。
　化合物番号a-8の化合物について、ワタアブラムシに対する効力試験を行った。本化合物は殺虫率が９０％以上であった。 (Test Example 2) Efficacy test against cotton aphids Cucumbers were sown in 3 inch pots. Adult female aphids were released on cucumbers 10 days after germination. The next day, the first-instar larvae produced were left behind and the adult females were removed. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass. This diluted solution was sprayed on the cucumber. After that, the cucumber was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%, and after 5 days, the life and death of the cotton aphid was examined, and the insecticidal rate was determined.
The efficacy test against Aphis gossypii was carried out for the compound of compound number a-8. This compound had an insecticidal rate of 90% or more.
（試験例３）　カンザワハダニに対する効力試験
　緑豆初生葉上に、岡山県産のカンザワハダニ雌成虫を５頭接種した。次いで乳剤（I）を化合物濃度１２５質量ｐｐｍになるように水で希釈して薬剤を得た。この薬剤を前記緑豆に散布し風乾させた。その後、温度２５℃、湿度６５％の恒温室内に置いた。散布から１０日間経過したときにダニの生死を調査した。試験は２反復で行った。
　第４表に示す化合物番号の化合物について、カンザワハダニに対する効力試験を行った。いずれの化合物もカンザワハダニに対して９０％以上の殺虫率を示した。 (Test Example 3) Efficacy test against Kanzawa spider mites Five adult female Kanzawa spider mites from Okayama prefecture were inoculated on the primary leaves of mung bean. The emulsion (I) was then diluted with water to a compound concentration of 125 ppm by mass to give a drug. This drug was sprayed on the mung beans and air-dried. Then, it was placed in a constant temperature room having a temperature of 25 ° C. and a humidity of 65%. The life and death of mites was investigated 10 days after spraying. The test was performed in two iterations.
The compounds with the compound numbers shown in Table 4 were tested for efficacy against Kanzawa spider mites. Both compounds showed an insecticidal rate of 90% or more against Kanzawa spider mites.
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
（試験例４）　ナミハダニに対する効力試験
　３寸鉢でインゲンを育苗し、初生葉上に、青森県産のナミハダニ雌成虫を８頭接種した。乳剤（I）を、本発明化合物の濃度が１２５質量ｐｐｍになるように水で希釈した。前記希釈液を前記インゲンに散布した。前記インゲンを、温度２５℃、湿度６５％の恒温室内に置いた。散布から１０日間経過したときにダニの生死を調査した。試験は２反復で行った。
　第５表に示す化合物番号の化合物について、ナミハダニに対する効力試験を行った。いずれの化合物も９０％以上の殺虫率を示した。 (Test Example 4) Efficacy test against Nami spider mites Eight green beans from Aomori prefecture were inoculated on the primary leaves by raising seedlings of green beans in a 3-inch pot. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass. The diluted solution was sprayed on the green beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of mites was investigated 10 days after spraying. The test was performed in two iterations.
The compound with the compound number shown in Table 5 was subjected to an efficacy test against spider mites. Both compounds showed an insecticidal rate of 90% or more.
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
　本発明化合物の中から無作為に選択したものが、上記のような効果を奏することから、本発明化合物は、例示しきれなかった化合物を含め、有害生物防除、特に殺虫、殺ダニ、外部寄生虫防除などの効果を有し、植物体に薬害を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない化合物であることが理解できる。 Randomly selected compounds of the present invention exert the above-mentioned effects. Therefore, the compounds of the present invention, including compounds that could not be exemplified, control pests, especially insecticide, acaricide, and ectoparasites. It can be understood that it is a compound that has effects such as insect control, does not cause chemical damage to plants, and has little toxicity to humans, livestock and fish, and has little effect on the environment.
　本発明のベンズアミド化合物は、農作物や衛生面で問題となる有害生物を防除することができる。特に農業害虫およびダニ類をより低濃度で効果的に防除することができる。さらに、人畜を害する外部寄生虫を効果的に防除することができる。 The benzamide compound of the present invention can control pests that pose a problem in terms of crops and hygiene. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, ectoparasites that harm humans and animals can be effectively controlled.

Claims (4)

  1. 　式（I）で表される化合物またはその塩。
    Figure JPOXMLDOC01-appb-C000001
     　式（I）中、
    　Ａｒは、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロアリール基を示し、
    　Ｒ1は、シアノ基、または置換若しくは無置換のチオカルバモイル基を示し、
    　Ｒ2は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示し、
    　Ｒ3は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示し、
    　Ｒ4は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示し、
    　Ｑは、式（Qa）または式（Qb）で表わされる基を示す。
    Figure JPOXMLDOC01-appb-C000002
     　前記式（Qa）および式（Qb）中、
    　矢印は結合位置を示し、
    　ｐ1は、括弧内のメチレンの数を示し且つ０または１であり、
    　ｐ2は、括弧内のメチレンの数を示し且つ０～２のいずれかの整数であり、
    　Ｘ1は、環上の置換基を示し且つハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、置換若しくは無置換のＣ１～６アルキルスルホニルオキシ基、または置換若しくは無置換のＣ１～６アルキルチオ基であり、
    　ｍは、Ｘ1の数を示し且つ化学的に許容される０～４のいずれかの整数であり、
    　Ｘ2は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、水酸基、または置換若しくは無置換のＣ１～６アルコキシ基を示し、
    　Ｙは、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示し、
    　Ｙ’は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示す。     A compound represented by the formula (I) or a salt thereof.
    Figure JPOXMLDOC01-appb-C000001
     In equation (I),
    Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered ring heteroaryl group.
    R 1 represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
    R 2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
    R 3 represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
    R 4 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
    Q indicates a group represented by the formula (Qa) or the formula (Qb).
    Figure JPOXMLDOC01-appb-C000002
     In the above equations (Qa) and (Qb),
    The arrow indicates the connection position,
    p 1 indicates the number of methylene in parentheses and is 0 or 1.
    p 2 indicates the number of methylene in parentheses and is an integer of 0 to 2.
    X 1 represents a substituent on the ring and is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6. It is an alkylthio group and
    m represents the number of X 1 and is a chemically acceptable integer from 0 to 4.
    X 2 represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
    Y represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6-membered heteroaryl group.
    Y'is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6-membered heteroaryl group. Indicates a group.
  2. 　請求項１に記載の化合物、およびその塩からなる群から選ばれる少なくとも１つを有効成分として含有する、有害生物防除剤。 A pest control agent containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.
  3. 　請求項１に記載の化合物、およびその塩からなる群から選ばれる少なくとも１つを有効成分として含有する、殺虫若しくは殺ダニ剤。 An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.
  4. 　請求項１に記載の化合物、およびその塩からなる群から選ばれる少なくとも１つを有効成分として含有する、外部寄生虫防除もしくは駆除剤。 An ectoparasite control or extermination agent containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.
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