WO2024005032A1 - Dérivé d'azépandione ou sel de celui-ci, agent de lutte contre les organismes nuisibles contenant ledit composé et procédé d'utilisation associé - Google Patents

Dérivé d'azépandione ou sel de celui-ci, agent de lutte contre les organismes nuisibles contenant ledit composé et procédé d'utilisation associé Download PDF

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WO2024005032A1
WO2024005032A1 PCT/JP2023/023869 JP2023023869W WO2024005032A1 WO 2024005032 A1 WO2024005032 A1 WO 2024005032A1 JP 2023023869 W JP2023023869 W JP 2023023869W WO 2024005032 A1 WO2024005032 A1 WO 2024005032A1
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substituted
halo
substituent
substituents
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一輝 藤居
浩介 深津
英二 安河内
憲司 原
弘亮 杉原
剛士 増田
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株式会社Adeka
日本農薬株式会社
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Publication of WO2024005032A1 publication Critical patent/WO2024005032A1/fr

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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
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
    • 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
    • A01N43/60—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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01P7/04—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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—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
    • C07D401/12—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 chain containing hetero atoms as chain links

Definitions

  • the present invention relates to an azepanedione derivative or a salt thereof, a pest control agent containing the compound, and a method for using the same.
  • Patent Documents 1 and 2 report certain azepanedione derivatives as pharmaceutical compounds. Furthermore, Patent Document 3 reports certain azepanedione derivatives as intermediates for pharmaceutical compounds. However, these documents do not describe or suggest the control activity of these compounds against harmful organisms such as pests in the field of agriculture and horticulture and parasites of animals.
  • the present inventors have conducted intensive research to develop new pest control agents, particularly agricultural and horticultural pest control agents, animal ectoparasite control agents, and animal endoparasite control agents.
  • the present invention was completed based on the discovery that a compound having an azepane-2,4-dione derivative as the carboxylic acid moiety of the carboxamide represented by formula (1) or a salt thereof is useful as a pest control agent.
  • R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 - C 6 ) cycloalkyl group; (a6) halo (C 1 - C 6 ) alkyl group; (a7) halo (C 2 - C 6 ) alkenyl group; (a8) halo (C 2 - C 6 ) alkynyl group (a9) halo(C 3 -C 6 )cycloalkyl group; (a10) substituted (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (
  • R 2a is (b1) A hydrogen atom; or (b2) a (C 1 -C 6 ) alkyl group.
  • R2b is (c1) A hydrogen atom; or (c2) a (C 1 -C 6 ) alkyl group.
  • R 3a is (d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Indicates the group.
  • R 3b is (e1) A hydrogen atom; or (e2) (C 1 -C 6 ) alkyl group.
  • R 4a is (f1) A hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group.
  • R 4b is (g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group.
  • R5 is (h1) (C 1 -C 6 ) alkyl group; (h2) (C 2 -C 6 ) alkenyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cyclo Alkyl group; (h5) halo (C 1 - C 6 ) alkyl group; (h6) halo (C 2 - C 6 ) alkenyl group; (h7) halo (C 2 - C 6 ) alkynyl group; (h8) halo ( C 3 -C 6 ) cycloalkyl group; (h9) substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h10) substituent group Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from B; (h11) phenyl group; (h
  • R6 is (i1) Hydrogen atom; (i2) (C 1 -C 6 ) alkyl group; (i3) (C 3 -C 6 ) cycloalkyl group; (i4) (C 1 -C 6 ) alkoxy group; or (i5) (C 1 -C 6 ) represents an alkylcarbonyl group.
  • X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group. show.
  • Y is an oxygen atom, a sulfur atom, or an NR 7 group (wherein R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
  • R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
  • Substituent group A is (j1) Cyano group; (j2) (C 1 -C 6 ) alkyl group; (j3) (C 2 -C 6 ) alkenyl group; (j4) (C 2 -C 6 ) alkynyl group; (j5) (C 3 - C6 ) cycloalkyl group; (j6) ( C1 - C6 ) alkoxy group; (j7) ( C1 - C6 ) alkylsulfanyl group; (j8) ( C1 - C6 ) alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; (j10) Halo (C 1 -C 6 ) alkyl group; (j11) Halo (C 2 -C 6 ) alkenyl group; (j12) Halo (C 2 - C 6 ) alkynyl group; (j13) halo(C 3 -C 6 )cycl
  • Substituent group B is (k1) Cyano group; (k2) (C 1 -C 6 ) alkyl group; (k3) (C 2 -C 6 ) alkenyl group; (k4) (C 2 -C 6 ) alkynyl group; (k5) (C 3 - C6 ) cycloalkyl group; (k6) ( C1 - C6 ) alkoxy group; (k7) ( C1 - C6 ) alkylsulfanyl group; (k8) ( C1 - C6 ) alkylsulfinyl group; (k9) (C 1 - C 6 ) alkylsulfonyl group; (k10) halo (C 1 - C 6 ) alkyl group; (k11) halo (C 3 - C 6 ) cycloalkyl group; (k12) halo (C 1 -C 6 ) alkoxy group; (k13) halo(C 1 -C 6
  • Substituent group C is (l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l4) Hydroxyl group; (l5) Carboxyl group; (l6) (C 1 - C 6 ) alkyl group; (l7) (C 2 - C 6 ) alkenyl group; (l8) (C 2 -C 6 ) alkynyl group; (l9) (C 1 -C 6 ) alkoxy group; (l10) (C 3 -C 6 ) cycloalkyl group; (l11) ( C 1 -C 6 )alkylsulfanyl group; (l12) (C 1 -C 6 )alkylsulfinyl group; (l13) (C 1 -C 6 )alkylsulfonyl group; (l14) halo(C 1 -C 6 )alkyl Group; (l15) Halo (C 2 - C 6 ) alkenyl group; (l16
  • Substituent group D is (m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m4) Amino group; (m5) Hydroxyl group; (m6) Carboxyl group; (m7) (C 1 - C 6 ) alkyl group; ( m8) (C 2 - C 6 ) alkenyl group; (m9) (C 2 - C 6 ) alkynyl group; (m10) (C 1 - C 6 ) alkoxy group; (m11) (C 3 - C 6 ) cycloalkyl Group; (m12) (C 1 -C 6 )alkylsulfanyl group; (m13) (C 1 -C 6 )alkylsulfinyl group; (m14) (C 1 -C 6 )alkylsulfonyl group; (m15) Halo (C 1 - C 6 ) alkyl group; (m16) halo (C 2 - C 6
  • the substituent group E is (n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n4) Amino group; (n5) Hydroxyl group; (n6) Carboxyl group; (n7) (C 1 - C 6 ) alkyl group; ( n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 - C 6 ) cycloalkyl group; (n10) (C 1 - C 6 ) alkylsulfanyl group; (n11) (C 1 - C 6 ) Alkylsulfinyl group; (n12) (C 1 - C 6 ) alkyl sulfonyl group; (n13) halo (C 1 - C 6 ) alkyl group; (n14) halo (C 1 - C 6 ) alkoxy group; (n15) halo (C 3 - C 6 ) cycloalkyl group; (n16) halo (C
  • N-(C 1 -C 6 )alkylaminosulfonyl group, or N,N-di(C 1 -C 6 )alkylaminosulfonyl group is not substituted.
  • R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 )cycloalkyl group; (a6) halo(C 1 -C 6 )alkyl group; (a10) substituted group having 1 to 3 substituents each independently selected from substituent group A (C 1 -C 6 ) alkyl group; (a12) (C 1 -C 6 ) alkoxycarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl group may be the same or different); (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1
  • Substituent group A is (j1) Cyano group; (j5) (C 3 - C 6 ) cycloalkyl group; (j6) (C 1 - C 6 ) alkoxy group; (j7) (C 1 - C 6 ) alkylsulfanyl group; (j8) (C 1 -C 6 )alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; and (j18) (C 1 -C 6 )alkoxycarbonyl group
  • Substituent group C is (l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l6) (C 1 -C 6 ) alkyl group; (l9) (C 1 -C 6 ) alkoxy group; (l11) (C 1 -C 6 ) alkylsulfanyl group; (l12) (C 1 -C 6 ) alkylsulfinyl group
  • R 1 is (a1) Hydrogen atom; (a3) (C 2 -C 6 ) alkenyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a10) 1 to 3 each independently selected from substituent group A (a16) a phenyl (C 1 -C 6 ) alkyl group; (a17) a substituted (C 1 -C 6 ) alkyl group having 1 to 5 substituents, each independently selected from substituent group C; Substituted phenyl (C 1 - C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a44) Phenyl group; (a45) Each independently from substituent group D Substituted phenyl group having 1 to 5 selected substituents on the ring; (a46) Pyridyl group; (a47) 1 to 4 substituents independently selected from substituent group D on the
  • the substituent group E is (n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) halo(C 1 -C 6 ) alkyl group; (n14) Halo(C 1 -C 6 )alkoxy group; (n19) (C 1 -C 6 )alkylcarbonylamino group; (n21) (C 1 -C 6 )alkylsulfonylamino group; (n33) Adjacent A methylenedioxy group
  • a pest control agent characterized by containing the compound described in any one of [1] to [3] or a salt thereof as an active ingredient
  • a pest control agent for agricultural and horticultural purposes characterized by containing the compound or its salts described in any one of [1] to [3] as an active ingredient
  • An animal ectoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3]
  • An animal endoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3]
  • a method for controlling agricultural and horticultural pests which comprises applying an effective amount of the agricultural and horticultural pest control agent according to [5] to plants or soil
  • a method for controlling animal ectoparasites which comprises orally or parenterally administering an effective amount of the animal ectoparasiticide according to [6] to a target animal; [10]
  • the compound or salt thereof of the present invention provides an azepanedione derivative represented by the general formula (1), which has excellent effects as a pest control agent.
  • halo means a "halogen atom” and represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.
  • (C 1 -C 6 )alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group.
  • (C 2 -C 6 )alkenyl group means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2 - Straight chain or branched alkenyl group having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc.
  • (C 2 -C 6 )alkynyl group refers to, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl- Straight chain or branched chain such as 1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group Indicates an alkynyl group having 2 to 6 carbon atoms.
  • (C 3 -C 6 )cycloalkyl group refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • (C 1 -C 6 )alkoxy group means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyl group.
  • (C 1 -C 6 )alkylsulfanyl group means, for example, a methylsulfanyl group, an ethylsulfanyl group, a normal propylsulfanyl group, an isopropylsulfanyl group, a normal butylsulfanyl group, a secondary butylsulfanyl group, a tertiary butylsulfanyl group, Normal pentylsulfanyl group, isopentylsulfanyl group, tertiary pentylsulfanyl group, neopentylsulfanyl group, 2,3-dimethylpropylsulfanyl group, 1-ethylpropylsulfanyl group, 1-methylbutylsulfanyl group, normal hexylsulfanyl group, iso Indicates a linear or branched alkylsulfanyl group having 1 to 6 carbon —
  • (C 1 -C 6 )alkylsulfinyl group means, for example, a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, Normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso It represents a linear or branched
  • (C 1 -C 6 )alkylsulfonyl group means, for example, a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, Normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso Indicates a linear or branched
  • (C 1 -C 6 )alkylcarbonyl group includes, for example, acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, It refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the above-mentioned (C 1 -C 6 ) alkyl group such as a pivaloyl group or a hexanoyl group.
  • (C 1 -C 6 )alkylcarbonylamino group means, for example, acetylamino group, propanoylamino group, butanoylamino group, 2-methylpropanoylamino group, pentanoylamino group, 2-methylbutanoyl
  • An alkylcarbonylamino group having 2 to 7 carbon atoms such as an alkylcarbonylamino group having the above-mentioned (C 1 -C 6 ) alkyl group such as an amino group, 3-methylbutanoylamino group, pivaloylamino group, hexanoylamino group, etc. shows.
  • (C 1 -C 6 )alkylsulfonylamino group means, for example, methylsulfonylamino group, ethylsulfonylamino group, normal propylsulfonylamino group, isopropylsulfonylamino group, normal butylsulfonylamino group, secondary butylsulfonylamino group , tertiary butylsulfonylamino group, normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group , 1-methylbutylsulfonylamino group, n-hex
  • N-(C 1 -C 6 )alkylaminocarbonyl group means, for example, N-methyl-aminocarbonyl group, N-ethylaminocarbonyl group, N-normalpropylaminocarbonyl group, N-isopropylaminocarbonyl group, -Normal butylaminocarbonyl group, N-isobutylaminocarbonyl group, N-secondary butylaminocarbonyl group, N-tertiary butylaminocarbonyl group, N-normalpentylaminocarbonyl group, N-isopentylaminocarbonyl group, N-tertiary Contains a linear or branched alkyl group having 1 to 6 carbon atoms, such as a liepentylaminocarbonyl group, N-neopentylaminocarbonyl group, N-normalhexylaminocarbonyl group, and N-isohexylaminocarbonyl group. It
  • (C 1 -C 6 )alkoxycarbonyl group means, for example, methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, It refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C 1 -C 6 ) alkoxy group, such as a tert-butoxycarbonyl group or a pentyloxycarbonyl group.
  • N-(C 1 -C 6 )alkylaminosulfonyl group means, for example, N-methylaminosulfonyl group, N-ethylaminosulfonyl group, N-normalpropylaminosulfonyl group, N-isopropylaminosulfonyl group, N-isopropylaminosulfonyl group, -Normal butylaminosulfonyl group, N-Secondary butylaminosulfonyl group, N-Tertiary butylaminosulfonyl group, N-Normalpentylaminosulfonyl group, N-Isopentylaminosulfonyl group, N-Tertiary pentylaminosulfonyl group, N -Neopentylaminosulfonyl group, N-(2,3-dimethylpropyl)aminosulfonyl group, N-(1
  • N,N-di(C 1 -C 6 )alkylaminosulfonyl group means, for example, N,N-dimethylaminosulfonyl group, N,N-diethylaminosulfonyl group, N,N-dinormalpropylaminosulfonyl group.
  • N,N-diisopropylaminosulfonyl group N,N-di-n-butylaminosulfonyl group, N,N-dise-butylaminosulfonyl group, N,N-ditertiarybutylaminosulfonyl group, N-methyl-N-ethyl Aminosulfonyl group, N-methyl-N-normalpropylaminosulfonyl group, N-methyl-N-isopropylaminosulfonyl group, N-methyl-N-normalbutylaminosulfonyl group, N-methyl-N-secondary butylaminosulfonyl group , N-methyl-N-tert-butylaminosulfonyl group, N-methyl-N-normalpentylaminosulfonyl group, N-methyl-N-isopentylaminosulfonyl group, N-methyl-N-tert-pent
  • Halo(C 1 -C 6 )alkyl group "Halo(C 2 -C 6 )alkenyl group”, “Halo(C 2 -C 6 )alkynyl group”, “Halo(C 1 -C 6 ) alkyl group”, respectively.
  • alkoxy group "halo(C 1 -C 6 )alkylsulfanyl group”, “halo(C 1 -C 6 )alkylsulfinyl group”, “halo(C 1 -C 6 )alkylsulfonyl group”, “halo(C 6 )alkylsulfonyl group” 3 -C 6 )cycloalkyl group", "Halo(C 1 -C 6 )alkylcarbonylamino group”, “Halo(C 1 -C 6 )alkylsulfonylamino group", “N-halo(C 1 -C 6 ) )alkylaminocarbonyl group”, “halo(C 1 -C 6 )alkoxycarbonyl group”, etc.
  • Examples of the salts of the compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate, Examples include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.
  • inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate
  • examples include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate
  • salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and
  • the compound represented by the general formula (1) of the present invention and its salts may have one or more asymmetric centers in its structural formula, and may have two or more optical isomers and diastereomers. In some cases, optical isomers exist, and the present invention includes all optical isomers and mixtures containing them in arbitrary proportions.
  • the compound represented by the general formula (1) of the present invention and its salts may have two types of geometric isomers derived from a carbon-carbon double bond in the structural formula, but the present invention It also includes all geometric isomers and mixtures containing them in arbitrary proportions.
  • the compound represented by the general formula (1) of the present invention and its salts may have a plurality of tautomers, but the present invention covers each tautomer and their arbitrary proportions. It also includes all mixtures contained in the above.
  • R 1 is the above (a1), (a2), (a3), (a4), (a5), (a6), (a10), (a12), (a14), (a15), (a16), (a17), (a18), (a19), (a24), (a25), (a26), (a27), (a36), (a37), (a40), (a41 ), (a44), (a45), (a46), (a47), (a50), (a51), (a52), (a53), (a54), (a55), (a60), (a61), The groups (a64), (a65), (a66), (a67), (a68), (a69), (a72), or (a73) are preferred, and the above (a1), (a3), (a6) , (a10), (a16), (a17), (a18), (a44), (a45), (a46), (a47), (a
  • R 2a is preferably the above-mentioned (b1) hydrogen atom.
  • R 2b is preferably the above-mentioned (c1) hydrogen atom.
  • R 3a is preferably the group (d1), (d2), (d3), or (d4) above, and more preferably the group (d1) or (d2) above.
  • R 3b is preferably the group (e1) or (e2) above.
  • R 4a is preferably the above group (f1) or (f2), and more preferably the above group (f1).
  • R 4b is preferably the group (g1) or (g2) above, and more preferably the group (g1) above.
  • R 5 includes the above (h1), (h3), (h4), (h5), (h11), (h12), (h13), (h14), (h15), (h16), (h17), (h18), (h19), (h20), (h25), (h26), (h27), (h28), (h31), (h32), (h41), (h42 ), (h53), or (h54) groups are preferred, and the above groups (h1), (h11), (h12), (h13), (h14), (h15), (h16), (h18), ( h19), (h25), (h28), (h31), (h42), or (h53) are more preferred.
  • X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfinyl group.
  • -C 6 )Alkylsulfonyl group is preferred, and hydroxyl group is more preferred.
  • substituent group B includes the above (k1), (k2), (k3), (k4), (k5), (k6), (k7), (k8), (k9). ), (k10), (k11), (k12), (k13), (k14), (k15), and (k16).
  • the substituent group C includes the above (l1), (l2), (l3), (l6), (l9), (l11), (l12), (l13), (l14 ), (l17), (l19), (l20), (l21), (l23), (l24), (l25), (l26), (l27), (l28), (l29), and (l30) It is preferably composed of the groups (l1), (l2), (l9), (l11), (l14), (l17), (l19), and (l20) described above. .
  • Manufacturing method 1 The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (2) by the following step [a].
  • R 1 , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 and Y are the same as above. ⁇
  • step [a] By reacting the compound represented by general formula (2) with the compound represented by general formula (3) in the presence of a base and an inert solvent, the general formula (1 A compound represented by -1) can be produced.
  • bases examples include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.
  • alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
  • organic bases such as (DBU), and the amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (2).
  • Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
  • Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
  • inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran
  • acetonitrile propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide
  • aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2
  • examples include alcohols such as -propanol, and these inert solvents can be used alone or in combination of two or more.
  • the amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
  • reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
  • Manufacturing method 2 The compound represented by general formula (1-2) of the present invention can be produced from the compound represented by general formula (2) by the following step [b].
  • R 1 , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 , R 6 and Y are the same as above.
  • L represents, for example, a halogen atom such as chlorine or bromine, or a leaving group such as an imidazolyl group or a trichloromethoxy group.
  • Examples include carbonates, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and DBU. It is usually used in an amount of 1 to 10 times the mole of the compound represented by general formula (2).
  • Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
  • Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
  • inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran
  • acetonitrile propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide
  • aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2
  • examples include alcohols such as -propanol, and these inert solvents can be used alone or in combination of two or more.
  • the amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
  • reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
  • the compound represented by general formula (2) which is the starting material for the compounds represented by general formulas (1-1) and (1-2) of the present invention, is prepared from Tetrahedron Letters, 1995, 36, 3659 or Journal of Heterocyclic Chemistry, 2017, 54, 1318, or according to the method described therein.
  • Pest control agents containing the compound represented by general formula (1) or its salts as an active ingredient of the present invention include agricultural and horticultural pest control agents, ectoparasite control agents for animals, and endoparasite control agents for animals. Can be applied as As an agricultural and horticultural pest control agent, it can be applied to control various agricultural and forestry, horticultural, grain storage pests, sanitary pests, nematodes, and other pests that damage paddy rice, fruit trees, vegetables, other crops, and flowers.
  • agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have physical properties suitable for various labor-saving application methods, systemic transfer activity, and suitable soil Excellent environmental safety such as persistence.
  • the agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have no effect on natural enemies, useful insects such as the European honey bee and bumble bee, and environmental organisms such as midges. Less is.
  • Lepidoptera lepidoptera
  • Lepidoptera include Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, and American white flycatcher.
  • Adoxophyes orana) Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Biston robustum Bucculatrix pyrivorella), Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Hellula undalis ), Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, Scopelodes contractus, Orgyia
  • Hemipteran pests include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc.
  • Aeschynteles maculatus Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopter us), Iseriya Icerya purchasi, Piezodorus hybneri, Lagynotomus elongatus, Thaia subrufa, Scotinophara lurida, Sitobion ibarae, Stariodes iwasaki i) , Aspidiotus destructor, Taylorilygus pallidulus, Myzusmumecola, Pseudaulacaspis prunicola, Acyrthosiphon pisum, Ana
  • Cavelerius saccharivorus Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae , spider Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Grapeleaf hopper (Erythroneura comes), Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspi s pentagona ), Pulvinaria kuwacola, Apolygus lucorum, Togo hempterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga
  • pests of the order Coleoptera include Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, and alfalfa weevil.
  • Diptera pests include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, and Chlorops oryzae.
  • Hymenoptera (Hymenoptera) pests include, for example, Pristomyrmex ponnes, wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, and Formica fusca japonica. , Wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., fire ant (Solenopsis spp.), Arge mali (Ochetellus glaber) etc.
  • thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, and Thrips flavus.
  • Thrips (Anaphothrips obscurus) , Cusukuda thrips (Liothrips floridensis), Gladiolus thrips (Thrips simplex), Black thrips (Thrips nigropilosus), Croton thrips (Heliothrips haemorrhoidalis), Swamp thrips (Pseudodendrothrips mori), Cosmos thrips (Microcephalothrips Abdominalis) , Thrips ( Leeuwenia pasanii), Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Tea thrips (Mycterothrips glycines) Scirtothrips dorsalis ), Choco Clothy Samewomes (DendrothRips Minowai), Haplo
  • Examples of insect pests in the order of Acari include Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, and Demodex canis.
  • Ticks such as Tetranychus viennensis, Tetranychus kanzawai, and Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, and Latrodectus ha.
  • termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., and Reticulitermes flaviceps amamianus. , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odon totermes formosanus) , Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.
  • Examples of pests of the order Cockroaches include the black cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Japanese cockroach (Blatta orientalis), the brown cockroach (Periplaneta brunnea), the Japanese cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach. (Periplaneta americana) etc.
  • nematodes examples include the strawberry nematode (Nothotylenchus acris), the rice nematode (Aphelenchoides besseyi), the northern nematode (Pratylenchus penetrans), the northern nematode (Meloidogyne hapla), the sweet potato nematode (Meloidogyne incognita), and the potato cyst nematode (Globodera).
  • rostochiensis Javan cat nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern coffeae (Pratylenchus coffeae), barley coffeae (Pratylenchus neglectus), and citrus nematode (Tylenchus semipenetrans).
  • molluscs examples include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana. can be mentioned.
  • the agricultural and horticultural pest control agent of the present invention has a strong insecticidal effect against other pests such as tomato absolutea (Tuta absoluta).
  • the agricultural and horticultural pest control agent containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention is suitable for use in agricultural and horticultural pest control agents that cause damage to paddy crops, field crops, fruit trees, vegetables, other crops, flowers, etc. Because it has a remarkable control effect against pests, it is necessary to remove seedlings, paddy fields, fields, fruit trees, vegetables, and other crops before the outbreak of pests or when the outbreak of pests is confirmed.
  • the intended effects of the agricultural and horticultural pest control agent of the present invention can be achieved by treating it on cultivation carriers such as seeds of flowers, paddy water, stems and leaves, or soil.
  • the compound of the present invention can be absorbed through the roots through or without the soil by treating the soil for raising seedlings of crops, flowers, etc., the soil for planting holes during transplanting, the roots of plants, irrigation water, cultivation water for hydroponic cultivation, etc.
  • a preferred form of use is application that takes advantage of the so-called permeation and migration properties.
  • Useful plants to which the agricultural and horticultural pest control agent of the present invention can be used are not particularly limited, but include, for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybean, etc.) , adzuki beans, fava beans, peas, kidney beans, peanuts, etc.), fruit trees/fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves/fruit vegetables (cabbage) , tomatoes, spinach, broccoli, lettuce, onions, green onions (morning onions, spring onions), green peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radish, turnips, lotus root, etc.), processed crops (cotton, hemp, bee
  • plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, and setoxydim. Also included are plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.
  • HPPD inhibitors such as isoxaflutole
  • ALS inhibitors such as imazethapyr and thifensulfuron-methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthetase inhibitors such as glufosinate
  • setoxydim setoxydim.
  • plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors,
  • plants that have been made resistant through classical breeding methods include rapeseed, wheat, sunflower, and rice, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale.
  • rapeseed, wheat, sunflower, and rice which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale.
  • sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl produced by classical breeding methods, and it is already sold under the trade name STS soybean.
  • SR corn is an example of a plant that has been made resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
  • acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
  • plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990).
  • mutant acetyl-CoA carboxylase that is resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol.
  • Plants resistant to acetyl-CoA carboxylase inhibitors can be created by introducing them into plants or by introducing mutations that confer resistance into plant acetyl-CoA carboxylase inhibitors.Furthermore, chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) is introduced into plant cells to introduce site-specific amino acids into plant acetyl-CoA carboxylase genes, ALS genes, etc. By introducing substitution mutations, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc., and the agricultural and horticultural pest control agent of the present invention can also be used for these plants. can.
  • insecticidal proteins derived from Bacillus cereus and Bacillus popilliae such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis; Insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain inhibitors; ribosome inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, ruffin, saporin, and
  • RIPs ribosome inactivating proteins
  • toxins expressed in such genetically modified plants include ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, VIP1, VIP2, VIP3, or VIP3A, etc.
  • Hybrid toxins, partially deleted toxins, and modified toxins of insecticidal proteins are also included. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant technology.
  • Cry1Ab which has a partially deleted amino acid sequence, is known as a partially deleted toxin.
  • a modified toxin has one or more amino acids substituted for the naturally occurring toxin.
  • the toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes.
  • the agricultural and horticultural pest control agent of the present invention can be used in combination with or systematized with those techniques.
  • the agricultural and horticultural pest control agent of the present invention is used as it is, or diluted or suspended with water etc. in an effective amount to control various pests and nematodes. It can be used on plants where outbreaks are predicted. For example, for pests and nematodes that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the stems and leaves, soaking seeds in chemicals, seed dressing, and cultivating methods can be used. Treatments such as seed treatment, soil full layer mixing, cropping application, bed soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc. It can also be absorbed and used.
  • the agricultural and horticultural pest control agent of the present invention can be used as it is, diluted with water, etc., or suspended in an effective amount for pest control in a place where the pests are expected to occur.
  • the agricultural and horticultural pest control agent of the present invention can be used as it is, diluted with water, etc., or suspended in an effective amount for pest control in a place where the pests are expected to occur.
  • it in addition to spraying on grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on house building materials, smoke, bait, etc.
  • Seed treatment methods include, for example, diluting a liquid or solid preparation or immersing the seeds in an undiluted liquid state to infiltrate the seeds, mixing a solid or liquid preparation with the seeds, or coating the seeds with powder. Examples include a method of treating and adhering to the surface of seeds, a method of mixing with an adhesive carrier such as a resin or polymer and coating the seeds, and a method of spraying near the seeds at the same time as planting.
  • seed used for the seed treatment refers to plants in the early stage of cultivation used for plant propagation, such as seeds, bulbs, tubers, seed potatoes, shoots, bulbs, scales, or cuttings for cultivation. Examples include plants for vegetative propagation.
  • soil or “cultivation carrier” for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, especially a support for growing roots, and the material is not particularly limited. However, any material that plants can grow on may be used, such as soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, and high-quality materials. It may also be a molecular substance, rock wool, glass wool, wood chips, bark, etc.
  • liquid preparations such as emulsions and flowables, or solid preparations such as wettable powders or granule wettable powders, are diluted with water as appropriate.
  • a method of spraying a method of spraying a powder, a method of smoking, etc.
  • Methods for applying to soil include, for example, applying liquid preparations to the base of plants or seedling beds without diluting them with water, or applying granules to the base of plants or seedling beds for raising seedlings.
  • Methods of spraying on seedbeds, etc. methods of spraying powders, wettable powders, granule wettable powders, granules, etc. before sowing or transplanting and mixing them with the entire soil, methods of spraying in planting holes, etc. before sowing or transplanting plants, etc. Examples include methods of dispersing powders, wettable powders, hydrated granules, granules, etc. in strips.
  • the dosage form may vary depending on the time of application, such as application at sowing, application during greening, application at transplanting, etc. It can be applied in a mold. It can also be applied by mixing with the soil, and it can be mixed with the soil and a powder, a granular wettable powder, a granule, etc., such as mixing with bed soil, mixing with soil covering, and mixing with the entire soil. You may simply apply the soil and various preparations in alternating layers.
  • solid preparations such as jumbo preparations, pack preparations, granules, and wettable powders
  • liquid preparations such as flowables and emulsions
  • a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as an emulsion or a flowable at a source where water flows into a rice field, such as a water outlet or an irrigation system, it can be applied in a labor-saving manner as water is supplied.
  • seeds or cultivation carriers close to the plants can be treated during the seeding to seedling-raising period.
  • treatment to the roots of plants under cultivation is suitable.
  • Spraying treatment can be performed using granules, or irrigation treatment can be carried out in liquid form by diluting or not diluting the agent with water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow the seeds.
  • Treatments during the sowing and seedling-raising stages of cultivated plants to be transplanted include direct treatment of seeds, as well as irrigation treatment with liquid chemicals or spraying treatment with granules on seedling beds.
  • the agricultural and horticultural pest control agent of the present invention is generally formulated into a form convenient for use according to conventional methods for pesticide formulations. That is, the compound represented by the general formula (1) of the present invention or its salts can be dissolved, separated, or suspended by blending them in an appropriate inert carrier or with an adjuvant as necessary in an appropriate ratio. It can be used by clouding, mixing, impregnating, adsorbing or adhering it into an appropriate dosage form, such as suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack, etc. Good.
  • the agricultural and horticultural pest control agent of the present invention may contain additive components commonly used in agricultural chemical formulations, if necessary.
  • additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, and antifreeze agents. , anti-caking agents, disintegrants, anti-decomposition agents and the like.
  • Other additives such as preservatives and plant pieces may be used as necessary.
  • These additive components may be used alone or in combination of two or more.
  • solid carriers examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as vegetable powders (e.g. sawdust, coconut shell, corncob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), etc. These may be used alone or in combination of two or more.
  • natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomace
  • liquid carriers examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF, etc.
  • ethers normal paraffin, naphthene, isoparaffin, kerosene, aliphatic hydrocarbons such as mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, dichloromethane, chloroform, carbon tetrachloride, etc.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, Polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxy Alkylene-a
  • binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weight of 6,000 to 20,000.
  • (meth)acrylic acid copolymers half esters of polyhydric alcohol polymers and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffins, terpenes, polyamide resins, polyacrylates, polyoxy Examples include ethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
  • thickeners examples include water-soluble polymers such as xanthan gum, guar gum, diurtan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, polysaccharides, high-purity bentonite, and fumed silica.
  • Inorganic fine powders such as silica, white carbon, etc.
  • coloring agent examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
  • antifreeze agents examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • adjuvants to prevent caking and promote disintegration include starch, alginic acid, polysaccharides such as mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer Examples include polymers.
  • decomposition inhibitors include drying agents such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds, and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It will be done.
  • preservatives examples include potassium sorbate and 1,2-benzothiazolin-3-one.
  • other aids such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers, etc. Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and it may be used by appropriately selecting from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural pest control agent of the present invention.
  • the appropriate amount is 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural pest control agent).
  • the amount of the agricultural and horticultural pest control agent of the present invention to be used depends on various factors, such as purpose, target pests, crop growth conditions, pest outbreak trends, weather, environmental conditions, dosage form, application method, application location, application timing, etc. Depending on the purpose, the amount of the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares.
  • the agricultural and horticultural pest control agent of the present invention can be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, and fungicides for the purpose of expanding the pests to be controlled and the appropriate period for control, or reducing the amount of pesticides. , biological pesticides, etc., and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the usage situation.
  • XMC 3,5-xylyl methylcarbamate
  • BPMC fenobucarb
  • Bt toxin insecticidal compounds CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O -4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, Acetoprole, acephate, abamectin,
  • Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, and acibenzolar-S-methyl. ), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin ), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate ), imibenconazole, inpyrfluxam, uniconazole,
  • Inorganic disinfectants sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate copper-based compounds such as sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, and oxine copper. , zinc sulfate, copper sulfate pentahydrate, and the like.
  • herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, icafolin, icafolin-methyl, aclonifen, azafenidin, acifluorfen, aziprotrine, azimus azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone ( amicarbazone), amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridi
  • biopesticides include, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV). ), insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc.
  • a microbial pesticide used as a fungicide for Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
  • a similar effect can be expected by mixing the microbial pesticides used in this invention with biological pesticides used as herbicides such as Xanthomonas campestris.
  • biopesticides such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z)-10-tetradecenyl acetate, (E,Z )-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icocen-10-one, 14-methyl-1 - It is also possible to use it in combination with a pheromone agent such as octadecene.
  • a pheromone agent such as octadecene.
  • the compound represented by general formula (1) of the present invention or a salt thereof is also suitable for controlling parasites in animals.
  • Animal parasites live in or on the host animal's body and cause a disadvantage to the host animal.
  • the compound represented by the general formula (1) of the present invention or a salt thereof can also be applied as an animal ectoparasiticide or an animal endoparasite controller.
  • examples of applicable animals include pigs, horses, Livestock such as cows, sheep, goats, rabbits, camels, water buffalo, deer, mink, and chinchillas, pet animals such as dogs, cats, small birds, and monkeys, laboratory animals such as rats, mice, golden hamsters, and guinea pigs, chickens, ducks, Examples include, but are not limited to, poultry such as ducks, quail, ducks, geese, and turkeys, and humans. It can also be applied to farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, as well as crustaceans and shellfish such as shrimp, crab, scallops, oysters, clams, and clams.
  • farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, as well as crustaceans and shellfish such as shrimp, crab, scallops, oysters, clams, and clams.
  • order Phthiraptera e.g. Bovicola Ovis, Bovicola Bovis
  • the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
  • the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
  • the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
  • the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
  • mites include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, and Haemaphysalis concinna.
  • fleas examples include Pulicidae and Ceratephyllus.
  • fleas belonging to the human flea family include dog flea (Ctenocephalidescanis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken flea (Echidnophaga gallinacea), Cheops rat flea (Xenopsylla cheopis), and blind rat flea (Leptopsylla segnis), the European rat flea (Nosopsyllus fasciatus), and the mountain rat flea (Monopsyllus anisus).
  • lice such as cow lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cow lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis),
  • lice such as Trichodectes canis, blood-sucking Diptera pests such as Tabanus trigonus, Culicoides schultzei, and Simulium ornatum can also be treated with the animal ectoparasit control method of the present invention. It is listed as an ectoparasite that can be controlled by anti-inflammatory agents.
  • the animal ectoparasiticide of the present invention can be prepared by using a suitable solid or liquid carrier in accordance with a commonly used pharmaceutical formulation, blending the agent in an appropriate proportion with an auxiliary agent as necessary, and dissolving, suspending, They may be mixed, impregnated, adsorbed or adhered, and prepared into a suitable dosage form, such as a liquid, emulsifier, cream, ointment, suspension, or aerosol, depending on the purpose of use.
  • the amount of the active ingredient in these preparations can range from 0.01 to 80.0 parts by weight per 100 parts by weight of the preparation.
  • the solid carrier or liquid carrier used carriers commonly used for veterinary drugs may be used, and liquid carriers are preferably used because they are easier to treat on target animals.
  • liquid carrier examples include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water.
  • alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water.
  • Auxiliary agents can be used as necessary, and surfactants, antioxidants, emulsifiers, etc.
  • adjuvants such as polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, Surfactants such as alkylaryl sorbitan monolaurate, alkylbenzene sulfonate, alkylnaphthalene sulfonic acid, lignosulfonate higher alcohol sulfate ester salt, glycol monoalkyl ether, glycols, sorbitan monooleate, sorbitan monolaurate, caprylic acid Examples include emulsifiers such as monoglyceride, capric acid monoglyceride, isostearic acid monoglyceride, and propylene glycol monocaprylate, and antioxidants such as BHA and BHT.
  • surfactants such as alkylaryl sorbitan monolaurate, alkylbenzene sulfonate, alkylnaphthalene sulfonic acid, lignosulfonate higher alcohol sulfate ester salt, glycol
  • the animal ectoparasiticide of the present invention may be administered to animals by a route that has the desired effect, such as locally, orally, parenterally, or subcutaneously, and is not particularly limited, but local administration is preferred.
  • spot-on treatment involves dropping a liquid drug onto the skin of the dorsal region of the target animal, pour-on treatment, which involves applying a liquid drug along the back line of the target animal, and administering a liquid aerosol drug using a spray method. It can be administered by a treatment method using a spray-on, spray lace, medicinal bath (dip), ear tag or collar carrying a medicinal agent, or the like.
  • the application amount may be appropriately selected from the range of usually about 0.1 to 500 mg of the active ingredient compound and usually about 0.01 to 20 ml of the pesticidal agent of the present invention per kg of body weight of the target animal.
  • active ingredients can be used in combination if necessary, such as afoxolaner, umifoxolaner, tigolaner, fluralaner, mivorilaner, modoflaner. ), lotilaner, surolaner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxifendazole, parabendazole, thiabendazole, triclabendazole, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, lafoxanide, cyphenothrin, flumethrin, permethrin, cyromazine, derquantel, diamphenetide, dicyclanil, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, abamectin, doramectin, emamectin, eprinome
  • the endoparasites that can be controlled by the animal endoparasite control agent of the present invention are broadly classified into protozoa and helminths.
  • Protozoa that parasitic humans include, for example, amoeba (Rhizopoda) such as Entamoeba histolytica, flagellates (Mastigophora) such as Leishmania, trypanosoma, and trichomonas, sporozoa (Sporozoea) such as malaria parasites and Toxoplasma gondii, and large intestine.
  • Ciliophora such as Balantidium are included, and helminths that parasitize humans include, for example, helminths, Anisakid, canis, hairy nematodes, pinworms, and hookworms (Zubini hookworm, American hookworm, Brazilian hookworm, etc.) , nematodes such as nematodes, gnathostomes, threadworms (filaria, Bancroft threadworms, Malayan threadworms, etc.), roundworms (Onchocerca), schizozoans, tricholates, strongyloids, etc.
  • helminths that parasitize humans include, for example, helminths, Anisakid, canis, hairy nematodes, pinworms, and hookworms (Zubini hookworm, American hookworm, Brazilian hookworm, etc.) , nematodes such as nematodes, gnathostomes, threadworms (filaria, Bancroft threadworms, Malayan thread
  • Acannthocephala (Acannthocephala), Gordiacea (Gordiacea), Hirudinea (Hirudinea), Schistosoma japonica, Schistosoma mansoni, Schistosoma bilharzia, Liver fluke, Trematodes (Trematoda) such as trematodes, leech-like trematodes, and lung flukes, tapeworms such as tapeworms, tapeworms mansoni, budworms, tapeworms great, tapeworms of the genus Taenia, tapeworms of the genus Taenia, (taenia taeniae, These include tapeworms (Cestoda) such as Taenia solium, hydatid (Echinococcus, etc.), patterned tapeworm, melid tapeworm, wire tapeworm, monkey bareheaded tapeworm, and tapeworm Nibellina. It is not limited.
  • Protozoa that parasitize animals belonging to mammals or birds other than humans include coccidia (Eimeria), Isospora (Isospora), Toxoplasma (Toxoplasma), Neospora (Neospora), Sarcocystis (Sarcocystis), Coccidia such as Besnoitia, Hammondia, Cryptosporidium, and Caryospora; Haemosporina such as Leucocytozoon and Plasmodium; ), Piroplasma such as Theileria, Anaplasma, Eperythrozoon, Heamobartonella, Rhrlichia, and other apicomplexans such as Hepatozoon.
  • coccidia Eimeria
  • Isospora Isospora
  • Toxoplasma Toxoplasma
  • Neospora Neospora
  • Sarcocystis Sarcocystis
  • Coccidia such as Besnoitia, Hammondia, Cryptospori
  • Haemogregarina Haemogregarina, Microspora, Encephalitozoon, Nosema, etc. Flagellates, Mastigophora, Trypanosoma, Leishmania, etc. Trichomonads such as Trypanosomatid, Chilomastix, Trichomonas, Monocercomonas, Histomonas, Vaccinonas such as Hexamita, Giardia, etc. Vaccinonadida, Sarcodina, amoebas such as Entamoeba, Ciliophora, Balantidium, Buxtonella, Entodinium. Such,
  • helminths that parasitize animals belonging to mammals or birds other than humans include nematodes such as Ascaris, Toxocara, Toxascaris, and Parascaris. ), roundworms (Ascarida) such as Ascaridia, Heterakis and Anisakis, Oxyurida such as Oxyuris and Passalurus, strongyles ( strongylus), Haemonchus, bovine Ostertagia, Trichostrongylus, Cooperia, Nematodirus, red Hystrongylus, Oesophagostomum, Chabertia, Ancylostoma, Uncinaria, Necator, Bunostomum, Bovine Lungworm (Dictyocaulus), pig lungworm (Metastrongylus), dog lungworm (Filaroides), cat lungworm (Aelurostrongulus), Cantonese schistosome (Angiostrongylus), tracheostomy beak (Syngamus),
  • Flukes include Fasciolata, such as Fasciola and Fasciolopsis, Paramphistomatidae, such as Homalogaster, Eurytrema, and lanceolates.
  • Diplocoelata such as Dicrocoelium, Pharyngostomum, Diplostomata such as Alaria, Echinostoma, Echinochasmus, etc.
  • Troglotrematoidea such as Echinostomata, Paragonimus, and Nanophyetus
  • Opisthorchiida such as Clonorchis
  • Heterophyes include Fasciolata, such as Fasciola and Fasciolopsis, Paramphistomatidae, such as Homalogaster, Eurytrema, and lanceolates.
  • Diplocoelata such as Dicrocoelium, Pharyngostomum, Diplostomata such as Alaria, Echinostoma
  • Heterophyida such as Metagonimus
  • Plagiorchiida such as Prosthogonimus
  • Schistosoma such as Schistoma
  • Pseudophylidea such as Diphyllobothrium, Spirometra, Anoplocephara, Paranoplocephala, Moniezia, Dog tapeworms (Dipylidium), wired tapeworms (Mesocestoides), legume-like tapeworms, hydatid tapeworms (Tenia), cat tapeworms (Hydatigera), multicephalic tapeworms (Multiceps), monocystic tapeworms (Echinococcus), polycystic tapeworms Echinococcus, Taenia, Taeniarhynchus, Hymenolepis, Vampirolepis, Raillietina, Amoebotaenia, etc. Cyclophyllidea, etc., Macracanthorhynch
  • helminths include, for example, the nematode genus Enoplida, Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp. spp.), examples of the genus Rhabditia include Micronema spp. and Strongyloides spp., and examples of the genus Strongylida include, for example, Stronylus. Species (Stronylus spp.), Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindrophorahynchus spp.
  • Cystocaulus spp. Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Paraphylloides spp.
  • Oxyurida for example, Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp. and Heterakis spp.
  • Ascaridiae include, for example, Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp. spp.), Anisakis spp., and Ascaridia spp.; examples of the Spiruride genus include Gnathosma spp., Physaloptera spp.
  • Thelazia spp. Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp., etc.
  • Examples of the genus Filariida include Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., and Deirofilaria. Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., etc.
  • Examples of Acanthocephala include Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., Prosthenorchis spp.
  • Subclasses of Monogenea of trematodes include, for example, Gyrodactylus spp., Dactylogyrusspp., and Polystoma spp.
  • subclasses of Digenea include, for example. , Diplostomum spp., Posthodiplostomum spp., Schistosomaspp., Trichobilharzia spp., Ornithbilharzia spp.
  • Austrobilharzia spp. Gigantobilharziaspp., Leucochloridium spp., Brachylaima spp., Echinostoma spp. spp.), Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Hypertrophic fluke spp.
  • tapeworms in the order Pseudophyllidea include Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., and Ligula spp. spp.), Bothridium spp., and Diplogonoporus spp., and in the Cyclophyllidea order, for example, Mesocestoides spp., Nachocephalic tapeworms.
  • the animal endoparasite control agent of the present invention is effective in controlling not only parasites living in the bodies of intermediate hosts and definitive hosts, but also parasites in the host organism. Furthermore, the compound represented by the general formula (1) of the present invention exhibits a controlling effect on parasites at all stages of development. For example, in protozoa, these include cysts, pretunicate types, trophozoites, meristems in the asexual stage, amoeboid bodies, gametocytes, gametes, fusion bodies, and sporophytes in the sexual stage. In nematodes, they are eggs, larvae, and adults.
  • the compound according to the present invention not only exterminates parasites within a living body, but also prevents parasite infection by applying it to the environment, which is a route of infection.
  • soil-transmitted infection from soil in fields and parks percutaneous infection from water systems such as rivers, lakes, wetlands, and rice fields, oral infection from feces of animals such as dogs and cats, saltwater fish, freshwater fish, and crustaceans.
  • feces of animals such as dogs and cats
  • saltwater fish freshwater fish
  • crustaceans It is possible to prevent oral infections from shellfish, raw livestock meat, etc., and infections from mosquitoes, horseflies, flies, cockroaches, ticks, fleas, lice, assassin bugs, chiggers, etc.
  • the animal endoparasite control agent of the present invention can be administered to humans, non-human mammals, or birds as a pharmaceutical for the purpose of treating or preventing parasitic diseases.
  • the administration method can be either oral administration or parenteral administration.
  • oral administration by incorporating into capsules, tablets, pills, powders, granules, fine granules, powders, syrups, enteric-coated agents, suspensions, pastes, or liquid drinks or feed for animals.
  • injections for parenteral administration, injections, drops, suppositories, emulsions, suspensions, drops, ointments, creams, liquids, lotions, sprays, aerosols, poultices, and tapes can be administered to mucous membranes or It is administered in a dosage form that maintains percutaneous absorption.
  • the optimal amount (effective amount) of the active ingredient should be determined depending on the type of infecting parasite, whether for treatment or prevention.
  • the dosage varies depending on the type and degree of infection, dosage form, etc., but in general, in the case of oral administration, it is in the range of about 0.0001 to 10,000 mg/kg body weight per day.
  • the dose ranges from about 0.0001 to 10,000 mg/kg body weight per day, administered in a single dose or in divided doses.
  • the concentration of the active ingredient in the animal internal parasite control agent of the present invention is generally about 0.001 to 100% by mass, preferably about 0.001 to 99%, and more preferably about 0.005 to 20% by mass.
  • the animal endoparasite control agent of the present invention may be a composition to be administered as it is, or may be a highly concentrated composition that is diluted to an appropriate concentration before use.
  • the other active ingredients described above can be used in combination as necessary for the purpose of reinforcing or supplementing the effects of the animal endoparasite control agent of the present invention.
  • two or more active ingredients may be mixed together before administration, or two or more different formulations may be administered separately.
  • 5-fluoro-2-aminopyridine (235 mg, 2.10 mmol) was dissolved in N,N-dimethylacetamide (15.0 mL), triethylamine (585 ⁇ L, 4.20 mmol), carbonyldiimidazole (372 mg, 2.31 mmol) was added at room temperature. After stirring the reaction solution at room temperature for 2 hours, 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (300 mg, 1.05 mmol) and DBU (300 ⁇ L, 2.10 mmol) were added.
  • Reference example 1 Reference Example 1-1 for the production of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione Production of 4-ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H-azepin-2(5H)-one
  • Reference example 2 Reference Example 2-1 for the production of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione Production of 4-ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
  • the reaction solution was heated to 110°C and stirred for 3 hours, but since the raw materials had not disappeared, copper(I) iodide (1.23 g, 6.44 mmol) and N,N-dimethylethylenediamine (692 ⁇ L) were added to the reaction solution. , 6.44 mmol) and heated at 140° C. for 8 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and a liquid separation operation was performed using ethyl acetate.
  • Reference example 3 Production reference example 3-1 of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione Production of 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
  • Formulation example 1 Compound of the present invention: 10 parts Xylene: 70 parts N-methylpyrrolidone: 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate: 10 parts The above ingredients are uniformly mixed and dissolved to obtain an emulsion.
  • Formulation example 2 Compound of the present invention: 3 parts Clay powder: 82 parts Diatomaceous earth powder: 15 parts The above ingredients are uniformly mixed and pulverized to obtain a powder.
  • Formulation example 3 Compound of the present invention: 5 parts Mixed powder of bentonite and clay: 90 parts Calcium ligninsulfonate: 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, kneaded, granulated, and dried to obtain granules.
  • Formulation example 4 Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to prepare a wettable powder.
  • Test example 1 Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released on Chinese cabbage seedlings to lay eggs, and two days after the release, the Chinese cabbage seedlings with eggs were treated with the compound represented by the general formula (1) of the present invention. The sample was immersed for about 30 seconds in a drug solution containing a drug as an active ingredient diluted to 500 ppm, air-dried, and then left in a constant temperature room at 25°C. The number of surviving insects was investigated after 6 days of immersion in the chemical solution, and the corrected mortality rate was calculated using the following formula, and judgment was made according to the following criteria. 1 ward 10 horses 3 consecutive races.
  • the compounds represented by the general formula (1) of the present invention exhibited significant insecticidal activity, especially compound numbers 1-52, 1-53, 1-54, 1-55, 1-58, 1-111. , 1-112, 1-118, 1-121, 1-124, 1-127, and 1-128 showed excellent activity against diamondback moths with a grade of B or better.
  • Test example 2 Test for evaluating the effect on the growth of Dirofilaria immitis A prescribed adjustment solution, 8-20 L-3 stage larvae of Dirofilaria immitis, and a DMSO diluted solution of the compound of the present invention were added to each hole of a 24-well plate. The final concentration was 10 ⁇ M. Seven days later, the larvae that had developed to the L-4 stage were counted, and the rate of growth inhibition from the L3 stage larva to the L4 stage larva was calculated.
  • compound numbers 1-5, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1 -20, 1-21, 1-40, 1-43, 1-44, 1-46, 1-48, 1-49, 1-50, 1-51, 1-55, 1-56, 1-57 , 1-58 and 1-117 showed a growth inhibition rate of 50% or more.
  • the compounds of the present invention and their salts have excellent effects as pest control agents.

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  • Pharmacology & Pharmacy (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Insects & Arthropods (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Abstract

Dans la production de cultures en agriculture, horticulture, etc, les dommages causés par les insectes nuisibles et similaires, qui restent significatifs, ainsi que l'apparition d'insectes nuisibles résistants aux médicaments existants, ont suscité une demande pour le développement d'un nouvel agent de lutte contre les insectes nuisibles en agriculture/horticulture. En outre, dans l'élevage d'animaux tels que le bétail et les animaux de compagnie (animaux domestiques), l'infection par un parasite provoque une douleur significative aux animaux et conduit à une énorme perte économique dans l'élevage, d'où la nécessité croissante de développer un nouvel agent de lutte contre les parasites externes et internes chez les animaux.　La présente invention concerne un composé représenté par la formule générale (1) {dans la formule, X représente un groupe hydroxy, etc, y représente un atome d'oxygène ou un atome de soufre, etc, R1 représente un groupe phényle substitué, etc, R2a, R2b, R3a, R3b, R4a et R4b représentent un atome d'hydrogène, etc ; R5 représente un groupe phényle substitué, etc, R6 représente un atome d'hydrogène, etc.} ou des sels de celui-ci, un agent de lutte contre les organismes nuisibles comprenant ledit composé en tant que principe actif, et un procédé d'utilisation associé.
PCT/JP2023/023869 2022-06-29 2023-06-27 Dérivé d'azépandione ou sel de celui-ci, agent de lutte contre les organismes nuisibles contenant ledit composé et procédé d'utilisation associé WO2024005032A1 (fr)

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JP2017503754A (ja) * 2013-11-20 2017-02-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ １−アリール−３−アルキルピラゾール殺虫剤
WO2021261562A1 (fr) * 2020-06-26 2021-12-30 日本農薬株式会社 Dérivé d'aryl tétrahydropyridine ou sel de celui-ci, insecticide le contenant et son procédé d'utilisation

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JP2002529450A (ja) * 1998-11-11 2002-09-10 バイエル アクチェンゲゼルシャフト フェニル−置換された環式エナミノン類
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WO2021261562A1 (fr) * 2020-06-26 2021-12-30 日本農薬株式会社 Dérivé d'aryl tétrahydropyridine ou sel de celui-ci, insecticide le contenant et son procédé d'utilisation

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