WO2018131690A1 - Ketone or oxime compound and herbicide - Google Patents

Ketone or oxime compound and herbicide Download PDF

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Publication number
WO2018131690A1
WO2018131690A1 PCT/JP2018/000711 JP2018000711W WO2018131690A1 WO 2018131690 A1 WO2018131690 A1 WO 2018131690A1 JP 2018000711 W JP2018000711 W JP 2018000711W WO 2018131690 A1 WO2018131690 A1 WO 2018131690A1
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Prior art keywords
alkyl
phenyl
optionally substituted
cycloalkyl
halo
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PCT/JP2018/000711
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French (fr)
Japanese (ja)
Inventor
沼田　昭
中村　俊之
有理 吉野
祐人 臼井
孝将 古橋
Original Assignee
日産化学工業株式会社
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Priority claimed from JP2017074726A external-priority patent/JP2020037515A/en
Application filed by 日産化学工業株式会社 filed Critical 日産化学工業株式会社
Publication of WO2018131690A1 publication Critical patent/WO2018131690A1/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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero 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
    • 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
    • A01N43/58—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
    • A01N43/72—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
    • A01N43/74—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
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/30—Phthalazines
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—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
    • 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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—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
    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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 with nitro or nitroso radicals directly attached to ring carbon atoms
    • C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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 with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids

Definitions

  • the present invention relates to a novel ketone or oxime compound or a salt thereof, and an agrochemical, particularly a herbicide, containing the ketone or oxime compound or a salt thereof as an active ingredient.
  • Patent Document 1 discloses a certain kind of ketone or oxime compound, but does not disclose any ketone or oxime compound according to the present invention.
  • the object of the present invention is a highly safe and effective herbicide active ingredient that reliably shows effects on various weeds at a lower dose, and has reduced problems such as soil contamination and effects on subsequent crops. It is to provide useful chemical substances.
  • the present inventors have found that the novel ketone or oxime compound represented by the following formula (1) according to the present invention has excellent herbicidal activity and target.
  • the present invention has been completed by discovering that it is a highly useful compound that has a high safety against certain crops and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects. That is, the present invention relates to the following [1] to [148].
  • Q is the ketone compound or salt thereof according to [1], wherein Q represents an oxygen atom.
  • Q is NOR 7 The oxime compound or salt thereof according to [1], wherein [4] R 8a , R 8b , R 9a And R 9b Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ⁇ C 6 Alkyl, —OH, C 1 ⁇ C 6 Alkoxy, C 1 ⁇ C 6 Alkylthio, C 1 ⁇ C 6 Alkylsulfinyl, C 1 ⁇ C 6 Alkylsulfonyl, -C (O) OH, C 1 ⁇ C 6 Alkoxycarbonyl, C 1 ⁇ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ⁇ C 6 Alkylaminocarbonyl or di (C 1 ⁇ C 6 ) Represents alkylaminocarbonyl, R 10 , R 11 And
  • R 6 Is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 6b Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 6b Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, phenyl, (Z j ) qj
  • the ketone compound or the salt thereof according to [4] which represents phenyl, D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38, substituted by: [6]
  • R 8a , R 8b , R 9a And R 9b Are each independently a hydrogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 Represents alkoxycarbonyl, R 10 , R 11 And R 12
  • Z 5 Is a ketone compound or a salt thereof according to [5], which represents
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -P (O) (OR 3c ) 2 Or -P (S) (OR 3c ) 2 Represents R 1a Is C 1 ⁇ C 8 Alkyl, R 5a Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 5a Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl
  • B represents B-1
  • A represents a hydrogen atom
  • R 6 Is C 1 ⁇ C 6 Alkyl or C 3 ⁇ C 8 Represents cycloalkyl
  • R 8a , R 9a , R 10 , R 11 And R 12 Represents a hydrogen atom
  • Z 4 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl or C 1 ⁇ C 6 Represents alkoxy
  • Z 8 Is a hydrogen atom or C 1 ⁇ C 6 Represents alkyl
  • R 41 Represents D3-58a or D3-60b
  • X 3 Is a halogen atom, C 1 ⁇ C 6 Alkyl or halo (C 1 ⁇ C 6 ) Represents alkyl
  • t5 represents an integer of 2
  • each X 3 May be the
  • A is R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, -S (O) r2 R 1a , -C (O) OR 1b Or -C (O) R 2 [2], the ketone compound according to [4] to [8], or a salt thereof.
  • A is R 5 Optionally substituted with (C 1 ⁇ C 6 ) The ketone compound or salt thereof according to [9], which represents alkyl.
  • A is -S (O) r2 R 1a [9] represents a ketone compound or a salt thereof.
  • A is -C (O) OR 1b [9] represents a ketone compound or a salt thereof.
  • A is —C (O)
  • R 2 [9] represents a ketone compound or a salt thereof.
  • R 1a Is phenyl or (Z a ) qa The ketone compound or a salt thereof according to [2], [4] to [13], which represents phenyl substituted with [15]
  • R 1a Represents a ketone compound or a salt thereof according to [14], which represents phenyl.
  • R 1a (Z a ) qa The ketone compound or a salt thereof according to [14], which represents phenyl substituted with [17]
  • R 1b Is C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, phenyl or (Z b ) qb
  • R 1b Is C 3 ⁇ C 8
  • the ketone compound or a salt thereof according to [17] which represents cycloalkyl.
  • R 1b Is C 2 ⁇ C 6 The ketone compound or a salt thereof according to [17], which represents alkenyl.
  • R 1b Is C 2 ⁇ C 6 The ketone compound or a salt thereof according to [17], which represents alkynyl.
  • R 1b Represents a ketone compound or a salt thereof according to [17], which represents phenyl.
  • R 1b (Z b ) qb The ketone compound or a salt thereof according to [17], which represents phenyl substituted with [23]
  • R 2 Is R 5f Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, (Z f ) qf
  • R 2 Is R 5f Optionally substituted with (C 1 ⁇ C 6 )
  • the ketone compound or salt thereof according to [23] which represents alkyl.
  • R 2 (Z f ) qf The ketone compound or a salt thereof according to [23], which represents phenyl substituted with [26]
  • R 2 Is a ketone compound or a salt thereof according to [23], which represents D2-102.
  • R 5 Is -OR 31 [2], the ketone compound according to [4] to [26], or a salt thereof.
  • R 5f Is phenyl or (Z f ) qf
  • R 5f Represents a ketone compound or a salt thereof according to [28], which represents phenyl.
  • R 5f (Z f ) qf The ketone compound or a salt thereof according to [28], which represents phenyl substituted with [31]
  • R 6 Is C 1 ⁇ C 6 Alkyl or C 3 ⁇ C 8
  • R 6 Is C 1 ⁇ C 6
  • the ketone compound or a salt thereof according to [31] which represents alkyl.
  • R 6 Is C 3 ⁇ C 8 The ketone compound or a salt thereof according to [31], which represents cycloalkyl.
  • R 8a , R 9a , R 10 , R 11 And R 12 Is a ketone compound or a salt thereof according to [2], [4] to [33], which represents a hydrogen atom.
  • R 31 Is C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 1 ⁇ C 6 Alkoxy (C 1 ⁇ C 4 ) Alkyl or —C (O) R 37 [2], the ketone compound according to [4] to [34] or a salt thereof.
  • R 31 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [35], which represents alkyl.
  • R 31 Is C 3 ⁇ C 8 The ketone compound or a salt thereof according to [35], which represents cycloalkyl.
  • R 31 Is C 1 ⁇ C 6 Alkoxy (C 1 ⁇ C 4 ) The ketone compound or salt thereof according to [35], which represents alkyl.
  • R 31 Is -C (O) R 37 [35] represents a ketone compound or a salt thereof.
  • R 37 Is C 1 ⁇ C 6 Alkyl, C 1 ⁇ C 6 Alkoxy, C 3 ⁇ C 8 The ketone compound or salt thereof according to [2], [4] to [39], which represents cycloalkyloxy or phenyl.
  • R 37 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [40], which represents alkyl.
  • R 37 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [40], which represents alkoxy.
  • R 37 Is C 3 ⁇ C 8 The ketone compound or a salt thereof according to [40], which represents cycloalkyloxy.
  • R 37 Represents a ketone compound or a salt thereof according to [40], which represents phenyl.
  • Z 4 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl or C 1 ⁇ C 6 The ketone compound or salt thereof according to [2], [4] to [44], which represents alkoxy.
  • Z 4 Represents a ketone compound or a salt thereof according to [45], which represents a halogen atom.
  • Z 4 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [45], which represents alkyl.
  • Z 4 Is C 3 ⁇ C 8 The ketone compound or a salt thereof according to [45], which represents cycloalkyl.
  • Z 4 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [45], which represents alkoxy.
  • Z 6 Is a hydrogen atom, a halogen atom or C 1 ⁇ C 6 The ketone compound or salt thereof according to [2], [4] to [49], which represents alkyl.
  • Z 6 Represents a ketone compound or a salt thereof according to [50], which represents a hydrogen atom.
  • Z 6 Represents a ketone compound or a salt thereof according to [50], which represents a halogen atom.
  • Z 6 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [50], which represents alkyl.
  • Z 8 Is a hydrogen atom or C 1 ⁇ C 6 The ketone compound or salt thereof according to [2], [4] to [53], which represents alkyl.
  • Z 8 Represents a ketone compound or a salt thereof according to [54], which represents a hydrogen atom.
  • Z 8 Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [54], which represents alkyl.
  • Z a Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The ketone compound or salt thereof according to [2], [4] to [56], which represents alkoxy.
  • Z a Represents a ketone compound or a salt thereof according to [57], which represents a halogen atom.
  • Z a Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [57], which represents alkyl.
  • Z a Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [57], which represents alkoxy.
  • Z b Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The ketone compound or salt thereof according to [2], [4] to [60], which represents alkoxy.
  • Z b Represents a ketone compound or a salt thereof according to [61], which represents a halogen atom.
  • Z b Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [61], which represents alkyl.
  • Z b Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [61], which represents alkoxy.
  • Z f Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The ketone compound or salt thereof according to [2], [4] to [64], which represents alkoxy.
  • Z f Represents a ketone compound or a salt thereof according to [65], which represents a halogen atom.
  • Z f Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [65], which represents alkyl.
  • Z f Is C 1 ⁇ C 6 The ketone compound or a salt thereof according to [65], which represents alkoxy.
  • R 8a , R 8b , R 9a And R 9b Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ⁇ C 6 Alkyl, —OH, C 1 ⁇ C 6 Alkoxy, C 1 ⁇ C 6 Alkylthio, C 1 ⁇ C 6 Alkylsulfinyl, C 1 ⁇ C 6 Alkylsulfonyl, -C (O) OH, C 1 ⁇ C 6 Alkoxycarbonyl, C 1 ⁇ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ⁇ C 6 Alkylaminocarbonyl or di (C 1 ⁇ C 6 ) Represents alkylaminocarbonyl, R 10 , R 11 And R 12 Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ⁇ C 6 Alkyl, —OH, C 1 ⁇ C 6 Alkoxy, C 1 ⁇ C 6 Alkoxy, C
  • R 6 Is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 6b Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 6b Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, phenyl, (Z j ) qj Represents phenyl, D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38, substituted with R 7 Is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 7b Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, R 7b Optionally substituted with (C 2 ⁇ C 6 ) Alkenyl, C 2 ⁇ C 6 Alkynyl, R 7b Optionally substituted with (C 2 ⁇ C 6 ) Alkynyl, -S (O) r1 R 15a , -C (O)
  • R 8a , R 8b , R 9a And R 9b are each independently a hydrogen atom, C 1 ⁇ C 8 Alkyl or C 1 ⁇ C 6 Represents alkoxycarbonyl, R 10 , R 11 And R 12 Each independently represents a hydrogen atom or C 1 ⁇ C 6 Alkyl represents a table, Z 5 Represents an oxime compound or a salt thereof according to [70], which represents a hydrogen atom.
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -P (O) (OR 3c ) 2 Or -P (S) (OR 3c ) 2 Represents R 1a Is C 1 ⁇ C 8 Alkyl, R 5a Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 3 ⁇ C 8 Cycloalkyl, R 5a Optionally substituted with (C 3 ⁇ C 8 ) Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl
  • A is R 5 Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, -S (O) r2 R 1a , -C (O) OR 1b Or -C (O) R 2 The oxime compound or a salt thereof according to any one of [3] and [69] to [73].
  • A is R 5 Optionally substituted with (C 1 ⁇ C 6 ) The oxime compound or a salt thereof according to [74], which represents alkyl.
  • A is -S (O) r2 R 1a The oxime compound or a salt thereof according to [74].
  • A is -C (O) OR 1b The oxime compound or a salt thereof according to [74].
  • [78] A is —C (O) R 2 The oxime compound or a salt thereof according to [74].
  • R 1a Is phenyl or (Z a ) qa The oxime compound or a salt thereof according to [3], [69] to [778], which represents phenyl substituted with [80]
  • R 1a Represents an oxime compound or a salt thereof according to [79], which represents phenyl.
  • R 1a (Z a ) qa The oxime compound or a salt thereof according to [79], which represents phenyl substituted with [82]
  • R 1b Is C 3 ⁇ C 8 Cycloalkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 Alkynyl, phenyl or (Z b ) qb
  • R 1b Is C 3 ⁇ C 8
  • the oxime compound or a salt thereof according to [82] which represents cycloalkyl.
  • R 1b Is C 2 ⁇ C 6 The oxime compound or a salt thereof according to [82], which represents alkenyl.
  • R 1b Is C 2 ⁇ C 6 The oxime compound or a salt thereof according to [82], which represents alkynyl.
  • R 1b Represents an oxime compound or a salt thereof according to [82], which represents phenyl.
  • R 1b (Z b ) qb The oxime compound or a salt thereof according to [82], which represents phenyl substituted with [88]
  • R 2 Is R 5f Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, (Z f ) qf
  • R 2 (Z f ) qf The oxime compound or a salt thereof according to [88], which represents phenyl substituted with [91]
  • R 2 Is an oxime compound or a salt thereof according to [88], which represents D2-102.
  • R 5 Is -OR 31 The oxime compound or a salt thereof according to any one of [3] and [69] to [91].
  • R 5f Is phenyl or (Z f ) qf The oxime compound or a salt thereof according to [3], [69] to [92], which represents phenyl substituted with [94]
  • R 5f Is an oxime compound or a salt thereof according to [93], which represents phenyl.
  • R 5f (Z f ) qf The oxime compound or a salt thereof according to [93], which represents phenyl substituted with: [96] R 6 Is C 1 ⁇ C 6 Alkyl or C 3 ⁇ C 8 The oxime compound or a salt thereof according to [3], [69] to [95], which represents cycloalkyl. [97] R 6 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [96], which represents alkyl. [98] R 6 Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to [96], which represents cycloalkyl.
  • R 7 Is a hydrogen atom, C 1 ⁇ C 6 Alkyl, R 7b Optionally substituted with (C 1 ⁇ C 6 ) Alkyl, C 2 ⁇ C 6 Alkenyl, C 2 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [98], which represents alkynyl.
  • R 7 Represents an oxime compound or a salt thereof according to [99], which represents a hydrogen atom.
  • R 7 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [99], which represents alkyl.
  • R 7b Is a halogen atom, cyano, C 3 ⁇ C 8 Cycloalkyl, -OR 31b The oxime compound or a salt thereof according to any one of [3] and [69] to [102].
  • R 7b Represents an oxime compound or a salt thereof according to [103], which represents a halogen atom.
  • R 7b Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to [103], which represents cycloalkyl.
  • R 7b Is -OR 31b
  • R 8a , R 9a , R 10 , R 11 And R 12 Represents an oxime compound or a salt thereof according to [3], [69] to [107], which represents a hydrogen atom.
  • R 31 Is C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl, C 1 ⁇ C 6 Alkoxy (C 1 ⁇ C 4 ) Alkyl or —C (O) R 37 The oxime compound or a salt thereof according to any one of [3] and [69] to [108]. [110] R 31 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [109], which represents alkyl. [111] R 31 Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to [109], which represents cycloalkyl.
  • R 31 Is C 1 ⁇ C 6 Alkoxy (C 1 ⁇ C 4 ) The oxime compound or a salt thereof according to [109], which represents alkyl.
  • R 31 Is -C (O) R 37 The oxime compound or a salt thereof according to [109], wherein [114] R 31b Is a hydrogen atom or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [113], which represents alkyl.
  • R 37 Is C 1 ⁇ C 6 Alkyl, C 1 ⁇ C 6 Alkoxy, C 3 ⁇ C 8 The oxime compound or salt thereof according to 3], [69] to [114], which represents cycloalkyloxy or phenyl.
  • R 37 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [115], which represents alkyl.
  • R 37 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [115], which represents alkoxy.
  • R 37 Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to [115], which represents cycloalkyloxy.
  • R 37 Is an oxime compound or a salt thereof according to [115], which represents phenyl.
  • Z 4 Is a halogen atom, C 1 ⁇ C 6 Alkyl, C 3 ⁇ C 8 Cycloalkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [119], which represents alkoxy.
  • Z 4 Represents an oxime compound or a salt thereof according to [120], which represents a halogen atom.
  • Z 4 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [120], which represents alkyl.
  • Z 4 Is C 3 ⁇ C 8 The oxime compound or a salt thereof according to [120], which represents cycloalkyl.
  • Z 4 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [120], which represents alkoxy.
  • Z 6 Is a hydrogen atom, a halogen atom or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [124], which represents alkyl.
  • Z 6 Represents an oxime compound or a salt thereof according to [125], which represents a hydrogen atom.
  • Z 6 Represents an oxime compound or a salt thereof according to [125], which represents a halogen atom.
  • Z 6 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [125], which represents alkyl.
  • Z 7 Is -OR 41 The oxime compound or salt thereof according to [3], [69] to [128], wherein [130] Z 8 Is a hydrogen atom or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [129], which represents alkyl.
  • Z 8 Represents an oxime compound or a salt thereof according to [130], which represents a hydrogen atom.
  • Z 8 Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [130], which represents alkyl.
  • Z a Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [132], which represents alkoxy.
  • Z a Represents an oxime compound or a salt thereof according to [133], which represents a halogen atom.
  • Z a Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [133], which represents alkyl.
  • Z a Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [133], which represents alkoxy.
  • Z b Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [136], which represents alkoxy.
  • Z b Represents an oxime compound or a salt thereof according to [137], which represents a halogen atom.
  • Z b Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [137], which represents alkyl.
  • Z b Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [137], which represents alkoxy.
  • Z f Is a halogen atom, C 1 ⁇ C 6 Alkyl or C 1 ⁇ C 6 The oxime compound or a salt thereof according to [3], [69] to [140], which represents alkoxy.
  • Z f Represents an oxime compound or a salt thereof according to [141], which represents a halogen atom.
  • Z f Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [141], which represents alkyl.
  • Z f Is C 1 ⁇ C 6 The oxime compound or a salt thereof according to [141], which represents alkoxy.
  • A is a hydrogen atom, C 1 ⁇ C 6 Alkyl or —C (O)
  • R 2 represents R 2 Is C 1 ⁇ C 6 Alkyl or (Z f ) qf Represents phenyl substituted with R 6 Is C 1 ⁇ C 6 Represents alkyl, R 7 Is C 1 ⁇ C 6 Represents alkyl, Z 7 Is -S (O) r
  • R 41 Represents Z 4 Is C 1 ⁇ C 6 Represents alkoxy
  • Z 6 And Z 8 represents a hydrogen atom
  • X 3 represents a halogen atom
  • qf represents an integer of 1 or 2
  • t5 represents the integer of 1; the oxime compound or a salt thereof according to [73].
  • the compound of the present invention has excellent herbicidal activity against various weeds and high safety against target crops, and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects, and has low Persistence and light environmental impact. Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields, and orchards.
  • the presence of a keto-enol structure tautomer represented by the following formula may be considered depending on the type and conditions of the substituent. Therefore, when the substituent A is introduced, B-1 is produced from the enol structure B-3, and B-2 is produced from the B-4, and the present invention includes all these structures.
  • geometric isomers of E-form and Z-form may exist depending on the type of substituent.
  • the present invention encompasses these E-form, Z-form, or a mixture containing E-form and Z-form in any ratio. To express.
  • the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.
  • halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the notation “halo” also represents these halogen atoms.
  • n- is “normal”
  • i- is “iso”
  • sec- is “sec-” or “s-” is “secondary”
  • tert- or “t “-”
  • Ph means phenyl.
  • C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, such as methyl, ethyl, n-propyl, i-propyl. , N-butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 1,1-dimethylpropyl, hexyl, octyl, and the like are listed as specific examples, each selected within the range of the designated number of carbon atoms. .
  • halo (C a -C b ) alkyl is linear or branched having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom
  • a chain-like hydrocarbon group is represented, and when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other.
  • phenyl (C a -C b ) alkyl is represented by a linear or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with phenyl.
  • the hydrocarbon groups having the above-mentioned meanings are exemplified, and for example, benzyl, 1-phenethyl and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule.
  • a saturated hydrocarbon group such as vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, 1,1-dimethyl-2-
  • propenyl and the like each selected within the range of the specified number of carbon atoms.
  • halo (C a -C b ) alkenyl in this specification refers to a straight or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom
  • An unsaturated hydrocarbon group which is chain-like and has one or more double bonds in the molecule.
  • these halogen atoms may be the same as or different from each other.
  • C a -C b alkynyl represents a linear or branched chain having a carbon number of a to b and an unsaturated group having one or more triple bonds in the molecule.
  • halo (C a -C b ) alkynyl refers to a straight or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom
  • An unsaturated hydrocarbon group which is chain-like and has one or more triple bonds in the molecule.
  • the halogen atoms may be the same as or different from each other.
  • Specific examples include 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl and the like. In the range of the number of carbon atoms.
  • C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms.
  • cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms. .
  • halo (C a -C b ) cycloalkyl in the present specification is a cyclic hydrocarbon group having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom It is possible to form a monocyclic or complex ring structure from 3 to 8 membered ring.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other.
  • C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms.
  • a monocyclic or complex ring structure from a member ring to an 8-member ring can be formed.
  • Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form.
  • 1-cyclopenten-1-yl, 2-cyclopenten-1-yl, 1-cyclohexen-1-yl, 2-cyclohexen-1-yl and the like can be mentioned as specific examples. Selected.
  • C a -C b alkoxy represents an alkyl-O— group having the above-mentioned meanings consisting of a to b carbon atoms, such as methoxy, ethoxy, n-propyloxy, i-propyl. Specific examples include oxy, n-butyloxy, i-butyloxy, sec-butyloxy, tert-butyloxy, and the like, each selected within the specified number of carbon atoms.
  • halo (C a -C b ) alkoxy represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, difluoromethoxy, trifluoromethoxy, chlorodifluoro Methoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2, -tetrafluoroethoxy, 2-chloro-1,1,2-tri Specific examples include fluoroethoxy, 1,1,2,3,3,3-hexafluoropropyloxy, and each is selected in the range of the designated number of carbon atoms.
  • C a -C b cycloalkyloxy in the present specification represents a cycloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, cyclopropyloxy, 2-methylcyclopentyloxy Specific examples include cyclohexyloxy, etc., and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkoxy (C c -C d ) alkyl is represented by a straight or branched chain in which a hydrogen atom bonded to a carbon atom has a carbon number of a to b.
  • methoxymethyl, 2-ethoxyethyl, 2,2-dimethoxyethyl and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylthio represents an alkyl-S— group having the above-mentioned meanings comprising a to b carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio, Specific examples include n-butylthio, i-butylthio, sec-butylthio, tert-butylthio and the like, each selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkylthio in the present specification represents a haloalkyl-S— group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylthio, trifluoromethylthio, chlorodifluoro Methylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethylthio, Specific examples include 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio, nonafluorobutylthio and the like Each selected within a range of each specified number of carbon atoms,
  • C a -C b alkylsulfinyl represents an alkyl-S (O) -group having the above-mentioned meanings having a carbon number of a to b, for example, methylsulfinyl, ethylsulfinyl, n- Specific examples include propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and the like, each selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkylsulfinyl in the present specification represents a haloalkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylsulfinyl, tri Fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl, nonafluorobutylsulfinyl Etc. are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkylsulfonyl in the present specification represents an alkyl-SO 2 -group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl. , I-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.
  • halo (C a -C b ) alkylsulfonyl in the present specification represents a haloalkyl-S (O) 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylsulfonyl, Trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trimethyl Specific examples include fluoroethylsulfonyl and the like, and each is selected within the range of the designated number of carbon atoms.
  • C a -C b alkoxycarbonyl represents an alkyl-O—C (O) — group having the above-mentioned meaning of a to b carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, Specific examples include n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, tert-butoxycarbonyl and the like, each selected within the range of the designated number of carbon atoms.
  • C a -C b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as acetyl, propionyl, butyryl, isobutyryl, Specific examples include valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl and the like, each selected within the range of the designated number of carbon atoms.
  • C a -C b alkylaminocarbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example methylcarbamoyl , Ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, sec-butylcarbamoyl, tert-butylcarbamoyl, etc. Selected.
  • di (C a -C b ) alkylaminocarbonyl means in the above meaning that the number of carbon atoms which may be the same or different from each other is a to b.
  • C a -C b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylamino, Specific examples include ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, tert-butylamino, etc., each selected within the specified number of carbon atoms.
  • di (C a -C b ) alkylamino has the above-mentioned meaning that the number of carbon atoms in which both hydrogen atoms may be the same or different from each other consists of a to b.
  • C a -C b alkylcarbonylamino represents an amino group in which one of the hydrogen atoms is substituted with an alkylcarbonyl group having the above-mentioned meaning consisting of a to b carbon atoms.
  • Specific examples include amino, propionylamino, isobutyrylamino, pivaloylamino, and the like, each selected within the specified number of carbon atoms.
  • C a -C b alkoxycarbonyl (C c -C d ) alkyl is a straight or branched chain in which a hydrogen atom bonded to a carbon atom has a carbon number of a to b.
  • R 20f the carbon hydrogen atoms bonded to carbon atoms are replaced by each of the substituents R 5, etc.
  • R 5 represents an alkyl group having the above-mentioned meaning of a to b atoms, Of being selected in the range of number of carbon atoms.
  • each substituent may be the same as or different from each other.
  • substituents may be the same or different from each other, and the substitution position may be a ring structure part, a side chain part, or May be in both.
  • the substituents when there are two or more substituents, the substituents may be the same or different from each other, and the substitution position may be a ring structure part, a side chain part, or May be in both.
  • each substituent may be the same as or different from each other.
  • An agrochemical in this specification means an insecticide / acaricide, a nematicide, a herbicide, a fungicide, etc. in the field of agriculture and horticulture.
  • the herbicides are weeds that adversely affect the growth of crops in paddy fields, upland fields, orchards, etc. It means chemicals for controlling weeds that grow randomly on non-agricultural land such as roadsides and track ends.
  • the weed in this specification means a plant that naturally occurs in non-agricultural lands such as paddy fields, upland fields, orchards, and turf fields, playgrounds, open spaces, parking lots, roadsides, track ends, and the like.
  • non-agricultural lands such as paddy fields, upland fields, orchards, and turf fields, playgrounds, open spaces, parking lots, roadsides, track ends, and the like.
  • weeds that occur in paddy fields for example, weeping pods (Potamogetonaceae) represented by potato moget (Potamogeton distinctus), etc.
  • weeds occurring in upland fields and orchards include, for example, solanaceae weeds represented by Solanum nigrum and Datura stramonium, and sourdaceae represented by American floras (Geraniaceae) weeds, Abutilon theophrasti and blue-tailed deer (Malvaceae) weeds represented by Sida spinosa, etc., Ipomoea purpurea and other morning glory (Ipomoea spps.) And convolvulus Spps.
  • solanaceae weeds represented by Solanum nigrum and Datura stramonium
  • sourdaceae represented by American floras (Geraniaceae) weeds
  • Ipomoea purpurea and other morning glory Ipomoea s
  • Sunflower Helianthus annuus
  • yellowfin Glinsoga ciliata
  • Atlantic horsetail (Cirsium arvense)
  • representatives such as Senecio vulgaris, Erigeron annus, and so on, Compositae weeds, Rorippa indica, Sinapis arvensis, and Capsella Bursapastoris Cruciferae weeds, Polygonum Blumei, Polygonum convolvulus, and other Polygonaceae weeds, Portulaca oleracea, and others album
  • Kano Chopodium ficifolium
  • Kochia scoparia and other representatives of the mosquito (Chenopodiaceae) weed
  • Stellaria media (Caryophyllaceae)
  • Weed Veronica persica, etc.
  • broad-leaved weeds such as legumes (Leguminosae) represented by Sesbania exaltata and Cassia obtusifolia, and broad-leaved weeds represented by Oxsalis courniculata (Oxsaldaseae) .
  • Wild sorghum (Sorgham bicolor), green squirrel (Panicum dichotomiflorum), Johnson grass (Sorghum halepense), Invier (Echinochloa crus-galli var. Crus-galli), Echinochloa crus-galli var.
  • Praticola ochae ach , Citrus (Digitaria ciliaris), Oats (Avena fatua), Blackgrass (Alopecurus myosuroides), Crimson (Eleusine indica), Enocorogusa (Setaria viridis), Aquinoenogurossa (Setaria faberi) and Suzumenoteppo (Alopecurus aeg)
  • Examples include weeds (Graminaceous weeds) and cyperaceous weeds (Cyperus rotundus, Cyperus esculentus).
  • weeds occurring in non-agricultural land in addition to those mentioned in the field and orchard weeds, for example, Poa annua, Taraxacum officinale, Conyza sumatrensis, Cardamine flexuosa, Examples include Trifolium repens, Hydrocotyle sibthorpioides, Planago asiatica, Cyperus brevifolius, Kyllinga brevifolia, and Equisetum arvense.
  • the crops in this specification include field crops, paddy field crops, horticultural crops, turf, fruit trees, etc., specifically, for example, corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut.
  • Crops such as buckwheat, sugar beet, rapeseed, sunflower, sugarcane and tobacco; solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbitae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), oilseed rape Vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (green onion, onion, garlic, asparagus) ), Celery vegetables (carrot, parsley, celery, a Ribbon Fufu, etc.), Rubiaceae vegetables
  • the above-mentioned crops include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthase inhibitors such as glufosinate, cetoxydim and the like.
  • Agricultural and horticultural plants that have been given resistance to acetyl-CoA carboxylase inhibitors, PPO inhibitors such as flumioxazin, herbicides such as bromoxynil, dicamba and 2,4-D by classical breeding methods and genetic engineering techniques included.
  • Examples of agricultural and horticultural plants that have been rendered tolerant by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. Already sold under the brand name. Similarly, there are soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods and are already sold under the trade name STS soybeans. Similarly, SR corn and the like are examples of agricultural and horticultural plants imparted with resistance to acetyl-CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • Agro-horticultural plants tolerated by acetyl-CoA carboxylase inhibitors are Procedures of the National Academy of Sciences of the United States of America (Proc.Natl.Acad) Sci. USA) 87, 7175-7179 (1990). Mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science 53, 728-746 (2005).
  • a plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation associated with imparting resistance into a plant by introducing a mutation into the plant acetyl-CoA carboxylase.
  • a base substitution mutation-introduced nucleic acid represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into plant cells to produce crops (acetyl CoA carboxylase / herbicide). Plants resistant to acetyl-CoA carboxylase inhibitors / herbicides can be created by inducing site-specific amino acid substitution mutations in the target) gene.
  • Examples of agricultural and horticultural plants that have been rendered tolerant by genetic engineering techniques include glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet varieties, RoundupReady (trade name), Aglisher GT ( AgrisureGT) (brand name) and other brand names are already sold.
  • glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet varieties RoundupReady (trade name), Aglisher GT ( AgrisureGT) (brand name) and other brand names are already sold.
  • Aglisher GT AgrisureGT
  • glufosinate-resistant maize, soybean, cotton, and rapeseed varieties using genetic engineering techniques which are already sold under trade names such as LibertyLink (trade name).
  • bromoxynyl-resistant cotton using genetic recombination technology has already been sold under the brand name BXN.
  • the agricultural and horticultural plants also include plants that can synthesize selective toxins known in the genus Bacillus using genetic recombination techniques.
  • insecticidal toxins expressed in such transgenic plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab derived from Bacillus thuringiensis , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other ⁇ -endotoxins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; scorpion toxin, spider toxin, bee toxin or Toxins produced by animals such as insect-specific neurotoxins; filamentous fungi toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, protease inhibitors such as patatin, cystatin
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins
  • Hybrid toxins, partially defective toxins, and modified toxins are also included.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. It is described in the patent literature. Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera pests, and Lepidoptera pests.
  • transgenic plants containing one or more insecticidal pest resistance genes and expressing one or more toxins are already known, and some are commercially available.
  • these genetically modified plants include YieldGard (trade name) (a corn variety expressing Cry1Ab toxin), YieldGard Rootworm (trade name) (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus (trade name) (a corn variety that expresses Cry1Ab and Cry3Bb1 toxins), Herculex I (trade name) (phosphino to confer resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing Tricine N-acetyltransferase (PAT), NuCOTN33B (trade name) (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollgard I) (trade name) (cotton varieties expressing Cry1Ac toxin), Bollgard II (trade name) (cotton varieties expressing Cry1Ac and Cry2
  • the crops include those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
  • anti-pathogenic substances include PR proteins (PRPs, described in EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) And substances produced by microorganisms such as those described in WO03 / 000906).
  • Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.
  • the above-mentioned crops also include crops imparted with useful traits such as oil component modification and amino acid content enhancing traits using genetic recombination techniques. Examples include VISTIVE (trade name) (low linolenic soybean with reduced linolenic content) or high-lysine (hig hoil) corn (corn with increased lysine or oil content).
  • the compound of the present invention represented by the formula (1) can be produced, for example, by the following method. Manufacturing method A [Wherein, Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , m and n are the same as above. Means the same.
  • This invention compound represented by this can be manufactured.
  • Some of the compounds represented by formula (3) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
  • Manufacturing method D (In the formula, A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , m and n are the same as above.
  • the compound represented by formula (1-3a) wherein A is A 3 and Z 7 is —OR 41 in the presence of a base may be reacted with the compound represented by formula (1): This invention compound can be manufactured.
  • the amount of the compound represented by formula (5) used here can be used in the range of 0.1 to 100 equivalents relative to 1 equivalent of the compound represented by formula (2-1a). If necessary, this reaction can be carried out using triethylamine, pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl). ) Bases such as amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate can be used.
  • the amount of the base that can be used can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (2-1a).
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • Manufacturing method E (In the formula, A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , m and n are the same as above. Represents the same meaning as A compound represented by formula (2-1b) and formula (5) [wherein R 41 and J a represent the same meaning as described above.
  • A is A 3 and Z 7 is —SR 41 by reacting the compound represented by A compound of the present invention represented by a certain formula (1-3b) can be produced.
  • a compound of the present invention represented by formula (1-1a-1) in which R 7 is a hydrogen atom in formula (1-1a); and formula (6) [wherein R 7c represents the above R 7 other than a hydrogen atom; The same meaning is represented, and J a represents the same meaning as described above.
  • the compound represented by formula (1-1a-2) is optionally reacted in the presence of a base, wherein R 7c represents the same meaning as R 7 other than a hydrogen atom.
  • This invention compound represented by this can be manufactured.
  • the amount of the compound represented by the formula (6) used here can be used in the range of 0.1 to 100 equivalents relative to 1 equivalent of the compound represented by the formula (1-1a-1). If necessary, this reaction can be carried out using triethylamine, pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl).
  • Bases such as amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate can be used.
  • the amount of the base that can be used can be used in the range of 0.1 to 100 equivalents with respect to the compound represented by the formula (1-1a-1).
  • This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane.
  • a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3
  • the reaction temperature can be set to any temperature from ⁇ 80 ° C. to the reflux temperature of the reaction mixture.
  • the reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
  • Production method A to production method F may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.
  • the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent.
  • This invention compound can be obtained.
  • it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
  • Reaction formula 1 [Wherein A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , X 3a , m and n represents the same meaning as described above. ] Equation (2-2) wherein, J b represents a halogen atom, -OSO 2 Me, a leaving group such as -OSO 2 CF 3.
  • X 3a and s4 represent the same meaning as described above. Can be produced.
  • the compound represented by the formula (3-1a) is reacted with the compound represented by the formula (3-1) according to a known method known in the literature, for example, a method described in International Publication No. 2004/087686. Can be produced.
  • the compound represented by the formula (2-2) used here can be produced according to a known method described in, for example, International Publication No. 2016/098899.
  • Some of the compound represented by formula (7-1) and the compound represented by formula (7-2) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
  • Some of the compounds represented by the formula (2-1b) used in the production method E are known compounds and can be produced, for example, by the method of the following reaction formula 2.
  • Reaction formula 2 [In the formula, A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , m and n are the same as above. Means the same. ] Equation (2-2) wherein, J b are as defined above. And a compound represented by formula (8): wherein R 103 represents C 1 -C 10 alkoxycarbonyl (C 1 -C 6 ) alkyl.
  • Reaction formula 1 and reaction formula 2 may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.
  • an inert gas atmosphere such as nitrogen or argon if necessary.
  • each of the production intermediates that are the raw material compounds of Production Method D and Production Method E can be obtained by carrying out ordinary post-treatment.
  • each production intermediate produced by these methods can be used as it is in the subsequent step without isolation and purification.
  • ketone or oxime compound represented by the formula (1) included in the present invention that can be produced by using these methods include the following structural formulas [1] -1 to [1] -143. And the compounds represented. However, the compounds represented by the structural formulas [1] -1 to [I] -143 are for illustrative purposes, and the ketone or oxime compounds included in the present invention are not limited to these. Absent.
  • the substituent described as Me represents a methyl group
  • Et represents an ethyl group
  • n-Pr and Pr-n represent normal propyl groups
  • Pr-i are isopropyl groups
  • c-Pr and Pr-c are cyclopropyl groups
  • n-Bu and Bu-n are normal butyl groups
  • s-Bu and Bu-s are secondary butyl groups
  • i- Bu and Bu-i are isobutyl groups
  • t-Bu and Bu-t are tertiary butyl groups
  • c-Bu and Bu-c are cyclobutyl groups
  • n-Pen and Pen-n are normal pentyl groups
  • c -Pen and Pen-c are cyclopentyl groups
  • n-Hex and Hex-n are normal hexyl groups
  • c-Hex and Hex-c are cyclohexyl groups
  • D2-108, D3-3a, D3-18b, D3-21a, D3-21b, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-58b , D3-60a, D3-60b and D3-65a represent the following structures.
  • the numbers described in the above structural formula represent the substitution position of the substituent X 3.
  • the description “D3-18b [6-Cl]” is “6-chlorobenzoxazole-2 Represents an “-yl group”. [-] Represents no substitution.
  • the descriptions A2a, A2b, A2c, A2d, A2e, A2f, A2g and A2h represent the following structures:
  • the numbers described in the above structural formulas represent the substitution positions of the substituents Z a , Z b and Z f. Represents a benzoyl group. In addition, those without parentheses indicate no substitution.
  • Examples of production intermediates of ketones or oxime compounds represented by the structural formulas [1] -1 to [1] -143 are shown in Tables 3 and 4.
  • the production intermediate of the inventive compound is not limited to these.
  • Me represents a methyl group
  • Et represents an ethyl group
  • c-Pr and Pr-c represent a cyclopropyl group, respectively.
  • those that can be converted into acid addition salts according to a conventional method are, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrogen iodide.
  • Hydrohalic acid salts such as acids, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfone Salts of sulfonic acids such as acids, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid A salt of a carboxylic acid, inorganic acid salts such as n
  • those that can be converted into a metal salt according to a conventional method are, for example, alkali metal salts such as lithium, sodium, and potassium, calcium, and barium.
  • alkali metal salts such as lithium, sodium, and potassium, calcium, and barium.
  • An alkaline earth metal salt such as magnesium, or an aluminum salt.
  • the compound of the present invention can be used as a herbicide for paddy fields in any treatment method of soil treatment and foliage treatment under flooded water.
  • the compound of the present invention can be used as a herbicide for upland fields and orchards in any treatment method of soil treatment, soil admixture treatment, and foliage treatment.
  • the compound of the present invention can be used for any of soil treatment, soil mixing treatment and foliage treatment in non-agricultural lands such as lawns, playgrounds, open spaces, roadsides, and track ends in addition to the fields of agriculture and horticulture such as paddy fields, upland fields and orchards. It can also be used in the processing method.
  • the compound of the present invention in applying the compound of the present invention as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, a binder, a solid carrier.
  • a surfactant e.g., sodium sulfate, sodium sulfate, sodium sulfate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate
  • Examples of solid carriers include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and other minerals, calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicates.
  • Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as ⁇ -butyrolactone.
  • acid amides such as N-methylpyrrolidone and N-octylpyrrolidone
  • vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.
  • solid and liquid carriers may be used alone or in combination of two or more.
  • surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan.
  • Nonionic surfactant such as fatty acid ester, alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, Salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene polystyrene Anionic surfactants such as phenyl ether sulfate and phosphate, polycarboxylate and polystyrene sulfonate, cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, and amphoteric interfaces such as amino acid type and betaine type An activator is mentioned. The content
  • the compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.
  • other herbicides cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected.
  • a combination with a plurality of known herbicides is also possible.
  • the application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally an amount of 0.005 to 50 kg per hectare (ha) is appropriate as the amount of active ingredient.
  • Wettable compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, anti-caking agents and decomposition inhibitors.
  • Emulsified compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents and decomposition inhibitors.
  • Flowable agent compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, anti-freezing agents, thickeners, etc. It is done.
  • Dry flowable agent compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts
  • Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors, etc. .
  • Liquid Compound of the Present Invention 0.01-70 parts
  • Liquid carrier 20-99.99 parts Others 0-10 parts Others include, for example, antifreezing agents, spreading agents and the like.
  • Granules Invention compound 0.01 to 80 parts
  • Solid carrier 10 to 99.99 parts Others 0 to 10 parts
  • Others include, for example, binders, decomposition inhibitors and the like.
  • Powder Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 10 parts Others include, for example, drift inhibitors and decomposition inhibitors. In use, the preparation is sprayed as it is or diluted 1 to 10000 times with water.
  • composition Example 2 Milk Compound No. of the present invention. 1-001 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Industries, Ltd. trade name) The above is uniformly mixed to obtain an emulsion.
  • composition Example 3 Flowable Agent Compound No. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: trade name of Kao Corporation) Lnox 1000C 0.5 part (anionic surfactant: Toho Chemical Co., Ltd. trade name) Xanthan gum 0.02 parts Water 64.48 parts After uniformly mixing the above, wet milling to obtain a flowable agent.
  • Dry flowable agent Compound No. 1-001 75 parts Hightenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name) Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name) Carplex # 80 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name) After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and kneaded, granulated with an extrusion granulator, and dried to obtain a dry flowable agent.
  • the compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.
  • herbicides various insecticides, fungicides, plant growth regulators, synergists, and the like
  • cost reduction due to a decrease in the amount of applied medicine expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected.
  • a combination with a plurality of known herbicides is also possible.
  • Preferred herbicides for use in combination with the compounds of the present invention include, for example, acetochlor, acifluorfen, acronifen, alachlor, alloxydim, alloxydim sodium (Alloxydim-sodium), amethrin (ametryn), amicarbazone, amidosulfuron, aminocyclopirachlor, aminocyclopirachlor salts and esters (aminocyclopirachlor-salts and esters), aminopyralid ), Salts and esters of aminopyralid (aminopyralid-salts and esters), amiprophos-methyl, amitrol, anilofos, asuram, atrazine, azafenidin, Azimuth Azimsulfuron, beflubutamid, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bensulide, bensulide benta
  • safeners include AD-67, benoxacor, cloquintocet-mexyl, cyomerinil, dichlormid, dicyclonone, cyprosulfamide , Diethorate, DKA-24, dymron, fenclorazole-ethyl, fenclorim, hexim (HEXIM), flurazole, flxofenim, furilazole, Isoxadifen (isoxadifen), isoxadifen-ethyl, MCPA, mecoprop, meetcamifen, mefenpyr, mefenpyr-ethyl, mefenpyr-me diethyl), mephenate, MG-1 91, NA (Naphthalic anhydride), OM (Octamethylene-diamine), oxabetrinil, PPG-1292, R-29148 and the like. These components can be used alone or in admixture of two or
  • the present invention will be described in more detail by specifically describing, as examples, synthesis examples and test examples of ketones or oxime compounds represented by the formula (1) used as an active ingredient.
  • the present invention is not limited by these.
  • Step 1 Preparation of methyl 2- ⁇ 3- (5-bromo-2-methoxyphenyl) -4-hydroxy-2-oxocyclopent-3-en-1-yl ⁇ -3-oxobutanoate Methyl acetoacetate To a mixed solution of 1.45 g and 60 ml of acetonitrile, 17.7 g of potassium carbonate was added and stirred at room temperature for 30 minutes. To this mixed solution, a separately prepared mixed solution of 3 g of 2- (5-bromo-2-methoxyphenyl) cyclopent-4-ene-1,3-dione and 60 ml of acetonitrile was added and stirred at room temperature for 15 minutes.
  • Step 2 Preparation of 2- (5-bromo-2-methoxyphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one Methyl 2- ⁇ 3- (5-Bromo- 2-methoxyphenyl) -4-hydroxy-2-oxocyclopent-3-en-1-yl ⁇ -3-oxobutanoate 0.3 g, 2 ml of methanol and 2 ml of water were mixed with 0. 15 g was added and stirred at room temperature for 5 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure. 5 ml of water was added to the obtained residue, and then concentrated hydrochloric acid was added to adjust the pH to 1.
  • reaction mixture was extracted with 7 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.25 g of the desired product as a pale yellow solid. Melting point: 160-164 ° C
  • Step 3 Preparation of 2- (5-bromo-2-methoxyphenyl) -3-hydroxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one
  • 2- (5-bromo-2 To a mixed solvent of -methoxyphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one 0.25 g, methanol 4 ml and water 1 ml, 94 mg of O-methylhydroxylamine hydrochloride was added And stirred at room temperature for 2 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure.
  • Step 4 Preparation of 2- (5-bromo-2-methoxyphenyl) -3-methoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one 2- (5-bromo-2 -Methoxyphenyl) -3-hydroxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one in a mixed solution of 3.5 g and N, N-dimethylformamide 95 ml, 2 g of potassium carbonate and then dimethyl Sulfuric acid (1.8 g) was sequentially added, and the mixture was stirred at room temperature for 45 minutes.
  • Step 5 3-methoxy-2- ⁇ 2-methoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl ⁇ -5- ⁇ 2- (methoxy Preparation of imino) propyl ⁇ cyclopent-2-en-1-one 2- (5-bromo-2-methoxyphenyl) -3-methoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-ene-1 -To a mixed solution of 1 g of ONE, 1 g of bis (pinacolato) diboron and 5 ml of 1,4-dioxane, 0.38 g of potassium acetate, 0.21 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, [1,1 '-Bis (diphenylphosphino) ferrocene] palladium (II) dichloride 0.24 g of
  • the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 85 ° C. for 3 hours.
  • 3 ml of water was added to the reaction mixture, followed by extraction with 20 ml of ethyl acetate.
  • the obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 8: 1 to 1: 3) to obtain 1.1 g of the objective product as an orange oil. It was.
  • Step 6 Preparation of 2- (5-hydroxy-2-methoxyphenyl) -3-methoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one 3-methoxy-2- ⁇ 2 -Methoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl ⁇ -5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-ene-1 -A mixed solution of 0.9 g of ON and 9 ml of tetrahydrofuran was cooled to 0 ° C, and 0.25 g of sodium hydroxide and 0.6 ml of 30% by mass hydrogen peroxide were sequentially added.
  • Step 7 2- [5- ⁇ (6-Chloroquinoxalin-2-yl) oxy ⁇ -2-methoxyphenyl] -3-methoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-ene-1 Production of 2-one A mixed solution of 0.19 g of 2- (5-hydroxy-2-methoxyphenyl) -3-methoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one and 3 ml of acetonitrile 0.25 g of potassium carbonate and 0.13 g of 2,6-dichloroquinoxaline were added. After completion of the addition, the mixture was stirred at 80 ° C. for 2 hours.
  • reaction solution was allowed to cool to room temperature, 7 ml of water was added, and the mixture was extracted with 7 ml of ethyl acetate.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 8: 1 to 1: 2) to obtain 0.25 g of the desired product as a yellow oil. It was.
  • the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. After adding 5 ml of ethyl acetate to the obtained residue, it was washed with water. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with n-hexane-ethyl acetate (1: 1 to 1: 2 gradient) to obtain 19 mg of the objective product as a yellow oil.
  • the obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane: ethyl acetate (gradient 3: 1 to 1: 1) to obtain 0.13 g of the objective product as a white solid. . Melting point: 45-50 ° C
  • Step 1 2-ethylhexyl 3-[ ⁇ 4-methoxy-3- (2-methoxy-4- ⁇ 2- (methoxyimino) propyl ⁇ -5-oxocyclopent-1-en-1-yl) phenyl ⁇ Thio] propanoate 2- (5-Bromo-2-methoxyphenyl) -3-methoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one 200 mg and 1,4-dioxane In a 5 ml mixed solution, 0.2 g of N, N-diisopropylethylamine, 30 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, 130 mg of 2-ethylhexyl 3-mercaptopropionate, tris (dibenzylideneacetone) ) 24 mg of dipalladium was added sequentially.
  • Step 2 Preparation of 3-ethoxy-2- (5-mercapto-2-methoxyphenyl) -5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one 2-ethylhexyl 3- [ Of 0.2 g of ⁇ 4-methoxy-3- (2-methoxy-4- ⁇ 2- (methoxyimino) propyl ⁇ -5-oxocyclopent-1-en-1-yl) phenyl ⁇ thio] propanoate and 5 ml of ethanol To the mixed solution, 0.42 g of sodium ethoxide was added and stirred at room temperature for 2 hours.
  • Step 3 2- [5- ⁇ (6-Chloroquinoxalin-2-yl) thio ⁇ -2-methoxyphenyl] -3-ethoxy-5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-ene-1
  • 3-Ethoxy-2- (5-mercapto-2-methoxyphenyl) -5- ⁇ 2- (methoxyimino) propyl ⁇ cyclopent-2-en-1-one 63 mg and N, N-dimethylformamide 3 ml
  • 78 mg of potassium carbonate and 45 mg of 2,6-dichloroquinoxaline were sequentially added, followed by stirring at room temperature for 1 hour.
  • the obtained organic layer was washed with water, dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (4: 1 to 1: 1 gradient) to obtain 0.16 g of the objective product as a colorless oil. It was.
  • Step 2 Preparation of 5- (5-bromo-2-methoxyphenyl) -4-hydroxycyclopent-2-en-1-one (5-bromo-2-methoxyphenyl) (furan-2-yl) methanol 105 g was reacted by the method described in International Publication No. 2016/098899 to obtain 100 g of the objective product as a black oil.
  • Step 3 Preparation of 2- (5-bromo-2-methoxyphenyl) cyclopent-4-ene-1,3-dione 5- (5-Bromo-2-methoxyphenyl) -4-hydroxycyclopent-2-ene
  • 5- 5-Bromo-2-methoxyphenyl) -4-hydroxycyclopent-2-ene
  • the compound of the present invention can be synthesized according to the above production methods and examples.
  • Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 8 are shown in Tables 5 to 8, and examples of their production intermediates are shown in Tables 10 and 11.
  • the included ketone or oxime compounds and their intermediates are not limited to these.
  • Me indicates methyl
  • Et indicates ethyl
  • c-Pr and Pr-c indicate cyclopropyl
  • t-Bu and Bu-t indicate tertiary butyl.
  • C-Pen and Pen-c represent a cyclopentyl group
  • Hex-c represents a cyclohexyl group
  • Ph represents a phenyl group
  • “ ⁇ ” represents a triple bond.
  • D1-108, D2-1, D2-34, D2-56, D2-100, D2-101, D2-102, D2-108, D2-109, D2-110, D3-3a, D3-18b , D3-21a, D3-21b, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-60a and D3-60b have the following structures:
  • the substitution positions of the substituents X 2 , X 3 , Z f and Z j correspond to the numbers described in the above structural formulas.
  • the description represents “6-chloroquinoxalin-2-yl”.
  • “mp” represents “melting point”
  • * 1” represents “resin”
  • decomp Represents decomposition.
  • Test Example 1 Herbicidal effect test by pretreatment of weed generation under flooding conditions After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to make flooding conditions with a depth of 4 cm. After seeding nobies, firefly and koigi in the cup, rice seedlings at the 2.5 leaf stage were transplanted. On the day of sowing, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose and treated on the water surface. Plants were grown by placing the cup in a greenhouse at 25 to 30 ° C., and after 3 weeks of drug treatment, the effects on various plants were investigated according to the following criteria. Compound Nos.
  • Test Example 2 Herbicidal Effect Test by Weed Growth Season Treatment under Flooding Conditions After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to make a flooding condition with a depth of 4 cm. Nobies, firefly, and oak seeds were mixed in the cup and placed in a greenhouse at 25-30 ° C. to grow plants. When Nobies, Firefly and Konagi reached the 1st to 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage and treated on the water surface. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. However, Compound Nos.
  • Test Example 3 Herbicidal effect test by foliage treatment After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to obtain a water depth of 0.1 to 0.5 cm. Inobie, Azegaya, Tamagayatsuri, and rice seeds were sown and placed in a greenhouse at 25 to 30 ° C. to grow plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. However, Compound Nos.
  • Test Example 4 Herbicidal Effect Test by Soil Treatment Put sterilized large soil in a plastic box 21cm long, 13cm wide and 7cm deep, and then squirrel, green crocodile, black mulberry, blackgrass, Italian ryegrass, black croaker, ichibi, The seeds of Aogateto, Shiroza, Jacobe, Jaegula, Giant corn, corn, soybean, rice, wheat, beet and rapeseed were sown in spots and covered with about 1.5 cm. Next, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the soil surface.
  • Test Example 5 Herbicidal effect test by foliar treatment Put sterilized large soil in a plastic box 21cm long, 13cm wide, 7cm deep, pearl bark, green croaker, barnyardgrass, oats, blackgrass, Italian ryegrass, Atlantic calyx, Ichibi, Seeds of Aogateto, Shiroza, Jacobe, Jaegula, Giant corn, corn, soybean, rice, wheat, beet and rapeseed are spotted, covered with about 1.5 cm, and then grown in a greenhouse at 25 to 30 ° C did.
  • Table 17 The results are shown in Table 17.
  • the symbols in Tables 13 to 17 have the following meanings.
  • the treatment dose (g / ha) represents that the concentration was adjusted so that the number of grams (g) described was processed when converted per hectare (1 ha). .
  • the ketone or oxime compound of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

Abstract

[Problem] To provide a novel agrochemical, especially a novel herbicide. [Solution] A ketone or oxime compound represented by formula (1), and a herbicide which contains this compound. (In the formula, B represents B-1 or B-2; Q represents an oxygen atom or NOR7; A represents a hydrogen atom or the like; R6 represents a C1-C6 alkyl group or the like; R7 represents a C1-C6 alkyl group or the like; each of R8a and R9a represents a hydrogen atom or a C1-C6 alkoxycarbonyl group; each of R8b and R9b represents a hydrogen atom; Z4 represents a C1-C6 alkyl group or the like; Z7 represents -OR41; and R41 represents a heterocyclic ring such as D3-18a.)

Description

ケトン若しくはオキシム化合物及び除草剤Ketones or oxime compounds and herbicides
　本発明は、新規なケトン若しくはオキシム化合物又はそれらの塩、並びにケトン若しくはオキシム化合物又はそれらの塩を有効成分として含有する農薬、特に除草剤に関するものである。 The present invention relates to a novel ketone or oxime compound or a salt thereof, and an agrochemical, particularly a herbicide, containing the ketone or oxime compound or a salt thereof as an active ingredient.
　例えば、特許文献１には、ある種のケトン若しくはオキシム化合物が開示されているが、本発明に係るケトン若しくはオキシム化合物に関しては何ら開示されていない。 For example, Patent Document 1 discloses a certain kind of ketone or oxime compound, but does not disclose any ketone or oxime compound according to the present invention.
国際公開第２０１６／０９８８９９号International Publication No. 2016/098899
　本発明の目的は、より低薬量で各種雑草に対して効果を確実に示し、且つ、土壌汚染や後作物への影響等の問題が軽減された、安全性の高く、除草剤の有効成分として有用な化学物質を提供することである。 The object of the present invention is a highly safe and effective herbicide active ingredient that reliably shows effects on various weeds at a lower dose, and has reduced problems such as soil contamination and effects on subsequent crops. It is to provide useful chemical substances.
　本発明者らは、上記の課題解決を目標に鋭意研究を重ねた結果、本発明に係る下記式（１）で表される新規なケトン若しくはオキシム化合物が除草剤として優れた除草活性並びに対象となる作物に対する高い安全性を有し、且つ、ホ乳動物、魚類及び益虫等の非標的生物に対してほとんど悪影響の無い、極めて有用な化合物であることを見い出し、本発明を完成した。
　すなわち、本発明は下記〔１〕～〔１４８〕に関するものである。
　〔１〕
　式（１）：
Figure JPOXMLDOC01-appb-C000007
 ［式中、Ｂは、Ｂ－１又はＢ－２のいずれかで示される環を表し、
Figure JPOXMLDOC01-appb-C000008
 　Ｑは、酸素原子、硫黄原子又はＮＯＲ７を表し、
　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５で任意に置換された（Ｃ２～Ｃ６）アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ、－Ｃ（Ｏ）Ｒ２、－Ｃ（Ｓ）Ｒ２、－Ｐ（Ｏ）（ＯＲ３ｃ）２又は－Ｐ（Ｓ）（ＯＲ３ｃ）２を表し、
　Ｒ１ａは、Ｃ１～Ｃ８アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ１ｂ、Ｒ１ｃ、Ｒ１ｄ及びＲ１ｅは、各々独立してＣ１～Ｃ８アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ２は、水素原子、Ｃ１～Ｃ８アルキル、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ｆで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ｆで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルキルカルボニル、ベンゾイル、（Ｚｆ）ｑｆで置換されたベンゾイル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、－Ｎ（Ｒ４ａ）Ｒ３ａ、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｄ２－１～Ｄ２－５６、Ｄ２－１００Ｄ２－１００～Ｄ２－１０６及びＤ２－１０７は、下記の構造で表される環を表し、
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000010
 　Ｒ３ａ、Ｒ３ｂ、Ｒ４ａ及びＲ４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ｇで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｇで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ｇで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ｇで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ｇで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ３ｃは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
　Ｒ５は、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、－ＯＲ３１、－Ｓ（Ｏ）ｒ２Ｒ３１、ベンゾイル、（Ｚｆ）ｑｆで置換されたベンゾイル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ５ａ、Ｒ５ｂ及びＲ５ｇは、各々独立してハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ１～Ｃ６アルコキシ、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７表し、
　Ｒ５ｆは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＯＲｆ、－Ｓ（Ｏ）ｒ２Ｒｆ、－Ｎ（Ｒ４ｆ）Ｒ３ｆ、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ６は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ６ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ６ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ６ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ６ｂは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ３１ｂ、－Ｓ（Ｏ）ｒ１Ｒ３１ｂ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、ベンゾイル、（Ｚｊ）ｑｊで置換されたベンゾイル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ７ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ７ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、－Ｓ（Ｏ）ｒ１Ｒ１５ａ、－Ｃ（Ｏ）ＯＲ１５ｂ、－Ｃ（Ｓ）ＯＲ１５ｂ、－Ｃ（Ｏ）ＳＲ１５ｂ、－Ｃ（Ｓ）ＳＲ１５ｂ、－Ｃ（Ｏ）Ｒ１６、－Ｃ（Ｓ）Ｒ１６、－Ｐ（Ｏ）（ＯＲ１７ｃ）２、－Ｐ（Ｓ）（ＯＲ１７ｃ）２、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－４～Ｄ２－６、Ｄ２－８～Ｄ２－１０、Ｄ２－１２～Ｄ２－１９、Ｄ２－２１、Ｄ２－２３、Ｄ２－２５、Ｄ２－２７、Ｄ２－３０～Ｄ２－５５又はＤ２－５６を表し
　Ｒ７ｂは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ３１ｂ、－Ｓ（Ｏ）ｒ１Ｒ３１ｂ、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、ベンゾイル、（Ｚｊ）ｑｊで置換されたベンゾイル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００、Ｄ２－１０１～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ１５ａは、Ｃ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ１８）Ｒ１７、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ１５ｂは、各々独立してＣ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ１６は、水素原子、Ｃ１～Ｃ８アルキル、Ｒ２０ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０ｆで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０ｆで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルキルカルボニル、ベンゾイル、（Ｚｆ）ｑｆで置換されたベンゾイル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、－Ｎ（Ｒ１８）Ｒ１７、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ１７及びＲ１８は、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ１７ｃは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
　Ｒ２０は、各々独立してハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ１～Ｃ６アルコキシ、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ２０ｆは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＯＲｆ、－Ｓ（Ｏ）ｒ１Ｒｆ、－Ｎ（Ｒ４ｆ）Ｒ３ｆ、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ３１は、水素原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル、－Ｃ（Ｏ）Ｒ３７、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
　Ｒ３１ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル、－Ｃ（Ｏ）Ｒ３７、フェニル又は（Ｚｉ）ｑｉで置換されたフェニルを表し、
　Ｒ３７は、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ３～Ｃ８シクロアルキルオキシ、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
　Ｒｆは、水素原子、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、フェニル（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルキルカルボニル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００、Ｄ２－１０１～Ｄ２－１０６又はＤ２－１０７を表し、
　Ｒ３ｆ及びＲ４ｆは、各々独立してＣ１～Ｃ６アルキル又はベンゾイルを表し、
　Ｚ４は、水素原子、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル又は－ＮＨ２を表し、
　Ｚ５、Ｚ６及びＺ８は、各々独立して水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
　Ｚ７は、－ＯＲ４１又は－Ｓ（Ｏ）ｒＲ４１を表し、
　Ｒ４１は、Ｄ３－１ａ、Ｄ３－１ｂ、Ｄ３－２ａ、Ｄ３－２ｂ、Ｄ３－３ａ、Ｄ３－３ｂ、Ｄ３－４ａ、Ｄ３－４ｂ、Ｄ３－１８ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－２７ａ、Ｄ３－２７ｂ、Ｄ３－３２ａ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－５８ｂ、Ｄ３－５９ａ、Ｄ３－６０ａ、Ｄ３－６０ｂ又はＤ３－６５ａを表し、
　Ｄ３－１ａ、Ｄ３－１ｂ、Ｄ３－２ａ、Ｄ３－２ｂ、Ｄ３－３ａ、Ｄ３－３ｂ、Ｄ３－４ａ、Ｄ３－４ｂ、Ｄ３－１８ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－２７ａ、Ｄ３－２７ｂ、Ｄ３－３２ａ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－５８ｂ、Ｄ３－５９ａ、Ｄ３－６０ａ、Ｄ３－６０ｂ及びＤ３－６５ａは、下記の構造で表される環を表し、
Figure JPOXMLDOC01-appb-C000011
 　Ｘ２は、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｆ２、ｆ３、ｆ４、ｆ５、ｆ７、ｆ８、ｆ９、ｆ１０又はｆ１１が２以上の整数を表すとき、各々のＸ２は互いに同一であっても又は互いに相異なってもよく、更に、２つのＸ２が隣接する場合には、隣接する２つのＸ２は－ＣＨ＝ＣＨＣＨ＝ＣＨ－を形成することにより、それぞれのＸ２が結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子はハロゲン原子又はＣ１～Ｃ６アルキルによって任意に置換されていてもよく、
　Ｘ３は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル又はフェニルを表し、ｔ２、ｔ３、ｔ４又はｔ５が２以上の整数を表すとき、各々のＸ３は互いに同一であっても又は互いに相異なってもよく、
　Ｘ２ａ及びＸ４は、各々独立して水素原子、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル又はフェニルを表し、
　Ｚａは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｑａが２以上の整数を表すとき、各々のＺａは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺａが隣接する場合には、隣接する２つのＺａは－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺａが結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル又はＣ１～Ｃ６アルキルスルホニルによって任意に置換されてもよく、
　Ｚｂは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｑｂが２以上の整数を表すとき、各々のＺｂは互いに同一であっても又は互いに相異なってもよく、
　Ｚｆは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ、－ＯＲ５１、－Ｓ（Ｏ）ｒ２Ｒ５１又はフェニルを表し、ｑｆが２以上の整数を表すとき、各々のＺｆは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺｆが隣接する場合には、隣接する２つのＺｆは－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺｆが結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル又はＣ１～Ｃ６アルキルスルホニルによって任意に置換されてもよく、
　Ｚｊは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｑｊが２以上の整数を表すとき、各々のＺｊは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺｊが隣接する場合には、隣接する２つのＺｊは－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺｊが結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル又はＣ１～Ｃ６アルキルスルホニルによって任意に置換されてもよく、
　Ｒ５１は、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、フェニル（Ｃ１～Ｃ６）アルキル又はフェニルを表し、
　ｆ１、ｐ１、ｐ２及びｔ１は、各々独立して０又は１の整数を表し、
　ｆ２、ｒ、ｒ１、ｒ２及びｔ２は、各々独立して０、１又は２の整数を表し、
　ｍ、ｎ、ｆ３及びｔ３は、各々独立して０、１、２又は３の整数を表し、
　ｆ４及びｔ４は、各々独立して０、１、２、３又は４の整数を表し、
　ｆ５及びｔ５は、各々独立して０、１、２、３、４又は５の整数を表し、
　ｑａ、ｑｂ、ｑｆ及びｑｊは、各々独立して１、２、３、４又は５の整数を表し、
　ｆ６は、０、１、２、３、４、５又は６の整数を表し、
　ｆ７は、０、１、２、３、４、５、６又は７の整数を表し、
　ｆ８は、０、１、２、３、４、５、６、７又は８の整数を表し、
　ｆ９は、０、１、２、３、４、５、６、７、８又は９の整数を表し、
　ｆ１０は、０、１、２、３、４、５、６、７、８、９又は１０の整数を表し、
　ｆ１１は、０、１、２、３、４、５、６、７、８、９、１０又は１１の整数を表し、
　ｆ１２は、０、１、２、３、４、５、６、７、８、９、１０、１１又は１２の整数を表す。］で表されるケトン若しくはオキシム化合物又はそれらの塩。
　　〔２〕
　Ｑは、酸素原子を表す〔１〕記載のケトン化合物又はその塩。
　　〔３〕
　Ｑは、ＮＯＲ７を表す〔１〕記載のオキシム化合物又はその塩。
　　〔４〕
　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル又はジ（Ｃ１～Ｃ６）アルキルアミノカルボニルを表し、
　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルコキシカルボニル又はＣ１～Ｃ６アルキルカルボニルを表す〔２〕記載のケトン化合物又はその塩。
　　〔５〕
　Ｒ６は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ６ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７又はＤ２－３８を表す〔４〕記載のケトン化合物又はその塩。
　　〔６〕
　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシカルボニルを表し、
　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｚ５は、水素原子を表す〔５〕記載のケトン化合物又はその塩。
　　〔７〕
　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ、－Ｃ（Ｏ）Ｒ２、－Ｐ（Ｏ）（ＯＲ３ｃ）２又は－Ｐ（Ｓ）（ＯＲ３ｃ）２を表し、
　Ｒ１ａは、Ｃ１～Ｃ８アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５、Ｄ２－５６、Ｄ２－１００～Ｄ２－１０４又はＤ２－１０５を表し、
　Ｒ１ｂ、Ｒ１ｃ、Ｒ１ｄ及びＲ１ｅは、各々独立してＣ１～Ｃ８アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５又はＤ２－５６を表し、
　Ｒ３ａ、Ｒ３ｂ、Ｒ４ａ及びＲ４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ｇで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表す〔６〕記載のケトン化合物又はその塩。
　　〔８〕
　Ｂは、Ｂ－１を表し、
　Ａは、水素原子を表し、
　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
　Ｒ８ａ、Ｒ９ａ、Ｒ１０、Ｒ１１及びＲ１２は、水素原子を表し、
　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
　Ｚ６は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｚ８は、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ４１は、Ｄ３－５８ａ又はＤ３－６０ｂを表し
　Ｘ３は、ハロゲン原子、Ｃ１～Ｃ６アルキル又はハロ（Ｃ１～Ｃ６）アルキルを表し、ｔ５が２の整数を表すとき、各々のＸ３は互いに同一であっても又は互いに相異なってもよく、
　ｎ及びｒは、０を表し、
　ｍ及びｔ３は、１の整数を表し、
　ｔ５は、１又は２の整数を表す〔７〕記載のケトン化合物又はその塩。
　　〔９〕
　Ａは、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、又は－Ｃ（Ｏ）Ｒ２を表す〔２〕、〔４〕～〔８〕に記載のケトン化合物又はその塩。
　　〔１０〕
　Ａは、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキルを表す〔９〕に記載のケトン化合物又はその塩。
　　〔１１〕
　Ａは、－Ｓ（Ｏ）ｒ２Ｒ１ａを表す〔９〕に記載のケトン化合物又はその塩。
　　〔１２〕
　Ａは、－Ｃ（Ｏ）ＯＲ１ｂを表す〔９〕に記載のケトン化合物又はその塩。
　　〔１３〕
　Ａは、－Ｃ（Ｏ）Ｒ２を表す〔９〕に記載のケトン化合物又はその塩。
　　〔１４〕
　Ｒ１ａは、フェニル又は（Ｚａ）ｑａで置換されたフェニルを表す〔２〕、〔４〕～〔１３〕に記載のケトン化合物又はその塩。
　　〔１５〕
　Ｒ１ａは、フェニルを表す〔１４〕に記載のケトン化合物又はその塩。
　　〔１６〕
　Ｒ１ａは、（Ｚａ）ｑａで置換されたフェニルを表す〔１４〕に記載のケトン化合物又はその塩。
　　〔１７〕
　Ｒ１ｂは、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表す〔２〕、〔４〕～〔１６〕に記載のケトン化合物又はその塩。
　　〔１８〕
　Ｒ１ｂは、Ｃ３～Ｃ８シクロアルキルを表す〔１７〕に記載のケトン化合物又はその塩。
　　〔１９〕
　Ｒ１ｂは、Ｃ２～Ｃ６アルケニル表す〔１７〕に記載のケトン化合物又はその塩。
　　〔２０〕
　Ｒ１ｂは、Ｃ２～Ｃ６アルキニルを表す〔１７〕に記載のケトン化合物又はその塩。
　　〔２１〕
　Ｒ１ｂは、フェニルを表す〔１７〕に記載のケトン化合物又はその塩。
　　〔２２〕
　Ｒ１ｂは、（Ｚｂ）ｑｂで置換されたフェニルを表す〔１７〕に記載のケトン化合物又はその塩。
　　〔２３〕
　Ｒ２は、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、（Ｚｆ）ｑｆで置換されたフェニル又はＤ２－１０２を表す〔２〕、〔４〕～〔２２〕に記載のケトン化合物又はその塩。
　　〔２４〕
　Ｒ２は、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキルを表す〔２３〕に記載のケトン化合物又はその塩。
　　〔２５〕
　Ｒ２は、（Ｚｆ）ｑｆで置換されたフェニルを表す〔２３〕に記載のケトン化合物又はその塩。
　　〔２６〕
　Ｒ２はＤ２－１０２を表す〔２３〕に記載のケトン化合物又はその塩。
　　〔２７〕
　Ｒ５は、－ＯＲ３１を表す〔２〕、〔４〕～〔２６〕に記載のケトン化合物又はその塩。
　　〔２８〕
　Ｒ５ｆは、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表す〔２〕、〔４〕～〔２７〕に記載のケトン化合物又はその塩。
　　〔２９〕
　Ｒ５ｆは、フェニルを表す〔２８〕に記載のケトン化合物又はその塩。
　　〔３０〕
　Ｒ５ｆは、（Ｚｆ）ｑｆで置換されたフェニルを表す〔２８〕に記載のケトン化合物又はその塩。
　　〔３１〕
　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表す〔２〕、〔４〕～〔３０〕記載のケトン化合物又はその塩。
　　〔３２〕
　Ｒ６は、Ｃ１～Ｃ６アルキルを表す〔３１〕に記載のケトン化合物又はその塩。
　　〔３３〕
　Ｒ６は、Ｃ３～Ｃ８シクロアルキルを表す〔３１〕に記載のケトン化合物又はその塩。
　　〔３４〕
　Ｒ８ａ、Ｒ９ａ、Ｒ１０、Ｒ１１及びＲ１２は、水素原子を表す〔２〕、〔４〕～〔３３〕に記載のケトン化合物又はその塩。
　　〔３５〕
　Ｒ３１は、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル又は－Ｃ（Ｏ）Ｒ３７を表す〔２〕、〔４〕～〔３４〕に記載のケトン化合物又はその塩。
　　〔３６〕
　Ｒ３１は、Ｃ１～Ｃ６アルキルを表す〔３５〕に記載のケトン化合物又はその塩。
　　〔３７〕
　Ｒ３１は、Ｃ３～Ｃ８シクロアルキルを表す〔３５〕に記載のケトン化合物又はその塩。
　　〔３８〕
　Ｒ３１は、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキルを表す〔３５〕に記載のケトン化合物又はその塩。
　　〔３９〕
　Ｒ３１は、－Ｃ（Ｏ）Ｒ３７を表す〔３５〕に記載のケトン化合物又はその塩。
　　〔４０〕
　Ｒ３７は、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ３～Ｃ８シクロアルキルオキシ又はフェニルを表す〔２〕、〔４〕～〔３９〕に記載のケトン化合物又はその塩。
　　〔４１〕
　Ｒ３７は、Ｃ１～Ｃ６アルキルを表す〔４０〕に記載のケトン化合物又はその塩。
　　〔４２〕
　Ｒ３７は、Ｃ１～Ｃ６アルコキシを表す〔４０〕に記載のケトン化合物又はその塩。
　　〔４３〕
　Ｒ３７は、Ｃ３～Ｃ８シクロアルキルオキシを表す〔４０〕に記載のケトン化合物又はその塩。
　　〔４４〕
　Ｒ３７は、フェニルを表す〔４０〕に記載のケトン化合物又はその塩。
　　〔４５〕
　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表す〔２〕、〔４〕～〔４４〕記載のケトン化合物又はその塩。
　　〔４６〕
　Ｚ４は、ハロゲン原子を表す〔４５〕記載のケトン化合物又はその塩。
　　〔４７〕
　Ｚ４は、Ｃ１～Ｃ６アルキルを表す〔４５〕記載のケトン化合物又はその塩。
　　〔４８〕
　Ｚ４は、Ｃ３～Ｃ８シクロアルキルを表す〔４５〕記載のケトン化合物又はその塩。
　　〔４９〕
　Ｚ４は、Ｃ１～Ｃ６アルコキシを表す〔４５〕記載のケトン化合物又はその塩。
　　〔５０〕
　Ｚ６は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表す〔２〕、〔４〕～〔４９〕記載のケトン化合物又はその塩。
　　〔５１〕
　Ｚ６は、水素原子を表す〔５０〕記載のケトン化合物又はその塩。
　　〔５２〕
　Ｚ６は、ハロゲン原子を表す〔５０〕記載のケトン化合物又はその塩。
　　〔５３〕
　Ｚ６は、Ｃ１～Ｃ６アルキルを表す〔５０〕記載のケトン化合物又はその塩。
　　〔５４〕
　Ｚ８は、水素原子又はＣ１～Ｃ６アルキルを表す〔２〕、〔４〕～〔５３〕記載のケトン化合物又はその塩。
　　〔５５〕
　Ｚ８は、水素原子を表す〔５４〕記載のケトン化合物又はその塩。
　　〔５６〕
　Ｚ８は、Ｃ１～Ｃ６アルキルを表す〔５４〕記載のケトン化合物又はその塩。
　　〔５７〕
　Ｚａは、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシを表す〔２〕、〔４〕～〔５６〕に記載のケトン化合物又はその塩。
　　〔５８〕
　Ｚａは、ハロゲン原子を表す〔５７〕に記載のケトン化合物又はその塩。
　　〔５９〕
　Ｚａは、Ｃ１～Ｃ６アルキルを表す〔５７〕に記載のケトン化合物又はその塩。
　　〔６０〕
　Ｚａは、Ｃ１～Ｃ６アルコキシを表す〔５７〕に記載のケトン化合物又はその塩。
　　〔６１〕
　Ｚｂは、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシを表す〔２〕、〔４〕～〔６０〕に記載のケトン化合物又はその塩。
　　〔６２〕
　Ｚｂは、ハロゲン原子を表す〔６１〕に記載のケトン化合物又はその塩。
　　〔６３〕
　Ｚｂは、Ｃ１～Ｃ６アルキルを表す〔６１〕に記載のケトン化合物又はその塩。
　　〔６４〕
　Ｚｂは、Ｃ１～Ｃ６アルコキシを表す〔６１〕に記載のケトン化合物又はその塩。
　　〔６５〕
　Ｚｆは、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシを表す〔２〕、〔４〕～〔６４〕に記載のケトン化合物又はその塩。
　　〔６６〕
　Ｚｆは、ハロゲン原子を表す〔６５〕に記載のケトン化合物又はその塩。
　　〔６７〕
　Ｚｆは、Ｃ１～Ｃ６アルキルを表す〔６５〕に記載のケトン化合物又はその塩。
　　〔６８〕
　Ｚｆは、Ｃ１～Ｃ６アルコキシを表す〔６５〕に記載のケトン化合物又はその塩。
　　〔６９〕
　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル又はジ（Ｃ１～Ｃ６）アルキルアミノカルボニルを表し、
　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルコキシカルボニル又はＣ１～Ｃ６アルキルカルボニルを表す〔３〕記載のオキシム化合物又はその塩。
　　〔７０〕
　Ｒ６は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ６ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７又はＤ２－３８を表し、
　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、－Ｓ（Ｏ）ｒ１Ｒ１５ａ、－Ｃ（Ｏ）ＯＲ１５ｂ、－Ｃ（Ｓ）ＯＲ１５ｂ、－Ｃ（Ｏ）ＳＲ１５ｂ、－Ｃ（Ｓ）ＳＲ１５ｂ、－Ｃ（Ｏ）Ｒ１６、－Ｐ（Ｏ）（ＯＲ１７ｃ）２又は－Ｐ（Ｓ）（ＯＲ１７ｃ）２を表す〔６９〕記載のオキシム化合物又はその塩。
　　〔７１〕
　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、Ｃ１～Ｃ８アルキル又はＣ１～Ｃ６アルコキシカルボニルを表し、
　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子又はＣ１～Ｃ６アルキルを表を表し、
　Ｚ５は、水素原子を表す〔７０〕記載のオキシム化合物又はその塩。
　　〔７２〕
　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ、－Ｃ（Ｏ）Ｒ２、－Ｐ（Ｏ）（ＯＲ３ｃ）２又は－Ｐ（Ｓ）（ＯＲ３ｃ）２を表し、
　Ｒ１ａは、Ｃ１～Ｃ８アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５、Ｄ２－５６、Ｄ２－１００～Ｄ２－１０４又はＤ２－１０５を表し、
　Ｒ１ｂ、Ｒ１ｃ、Ｒ１ｄ及びＲ１ｅは、各々独立してＣ１～Ｃ８アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５又はＤ２－５６を表し、
　Ｒ３ａ、Ｒ３ｂ、Ｒ４ａ及びＲ４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ｇで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表し、
　Ｒ１５ａは、Ｃ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ１８）Ｒ１７、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５、Ｄ２－５６、Ｄ２－１００～Ｄ２－１０４又はＤ２－１０５を表し、
　Ｒ１５ｂは、Ｃ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５又はＤ２－５６を表し、
　Ｒ１７及びＲ１８は、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表す〔７１〕記載のオキシム化合物又はその塩。
　　〔７３〕
　Ｂは、Ｂ－１を表し、
　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ又は－Ｃ（Ｏ）Ｒ２を表し、
　Ｒ１ａは、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ又はＤ２－１０１を表し、
　Ｒ１ｂは、Ｃ１～Ｃ６アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表し、
　Ｒ１ｃは、フェニル又はＤ２－５６を表し、
　Ｒ１ｄは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１ｅは、フェニルを表し、
　Ｒ２は、Ｃ１～Ｃ６アルキル、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、キノリン－８－イル、－Ｎ（Ｒ４ａ）Ｒ３ａ、Ｄ２－１、Ｄ２－３４、Ｄ２－１００又はＤ２－１０２を表し、
　Ｒ３ａ及びＲ４ａは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ３ｂ及びＲ４ｂは、各々独立してＣ１～Ｃ６アルキルを表し、
　Ｒ５は、－ＯＲ３１、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
　Ｒ５ａは、ハロゲン原子を表し、
　Ｒ５ｂは、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はフェニルを表し、
　Ｒ５ｆは、ハロゲン原子、－ＯＲｆ、－Ｓ（Ｏ）ｒ２Ｒｆ、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ１Ｒ１５ａ、－Ｃ（Ｏ）ＯＲ１５ｂ又は－Ｃ（Ｏ）Ｒ１６を表し、
　Ｒ７ｂは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、－ＯＲ３１ｂ、フェニル、（Ｚｊ）ｑｊで置換されたフェニルを表し
　Ｒ８ａ、Ｒ９ａ、Ｒ１０、Ｒ１１及びＲ１２は、水素原子を表し、
　Ｒ１５ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１５ｂは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１６は、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又は－Ｎ（Ｒ１８）Ｒ１７を表し、
　Ｒ１７は、Ｃ１～Ｃ６アルキルを表し、
　Ｒ１８は、水素原子を表し、
　Ｒ３１は、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル又は－Ｃ（Ｏ）Ｒ３７を表し、
　Ｒ３１ｂは、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｒ３７は、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ３～Ｃ８シクロアルキルオキシ又はフェニルを表し、
　Ｒｆは、Ｃ１～Ｃ６アルキル、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
　Ｒ４１は、Ｄ３－３ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－６０ａ又はＤ３－６０ｂを表し、
　Ｚ６は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
　Ｚ８は、水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｘ３は、ハロゲン原子、ニトロ、シアノ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルコキシカルボニルを表し、ｔ２、ｔ３、ｔ４又はｔ５が２以上の整数を表すとき、各々のＸ３は互いに同一であっても又は互いに相異なってもよく、
　Ｚａは、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ又はＣ１～Ｃ６アルキルカルボニルアミノを表し、ｑａが２以上の整数を表すとき、各々のＺａは互いに同一であっても又は互いに相異なってもよく、
　Ｚｂは、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルコキシカルボニルを表し、
　Ｚｆは、ハロゲン原子、ニトロ、シアノ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、又はＣ１～Ｃ６アルコキシカルボニルを表し、ｑｆが２以上の整数を表すとき、各々のＺｆは互いに同一であっても又は互いに相異なってもよく、
　Ｚｊは、ハロゲン原子を表し、
　ｆ３、ｆ４、ｆ７、ｆ８、ｆ１０、ｎ及びｐ２は、０を表し、
　ｍ、ｑｂ、ｑｊ、ｔ２及びｔ４は、１の整数を表し、
　ｔ５及びｒは、各々独立して０、１又は２の整数を表し、
　ｔ３は、１又は２の整数を表す
　ｑａ及びｑｆは、各々独立して１、２又は３の整数を表し、
　ｒ１は、２の整数を表し、
　ｒ２は、０又は２の整数を表す〔７２〕記載のオキシム化合物又はその塩。
　　〔７４〕
　Ａは、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、又は－Ｃ（Ｏ）Ｒ２を表す〔３〕、〔６９〕～〔７３〕に記載のオキシム化合物又はその塩。
　　〔７５〕
　Ａは、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキルを表す〔７４〕に記載のオキシム化合物又はその塩。
　　〔７６〕
　Ａは、－Ｓ（Ｏ）ｒ２Ｒ１ａを表す〔７４〕に記載のオキシム化合物又はその塩。
　　〔７７〕
　Ａは、－Ｃ（Ｏ）ＯＲ１ｂを表す〔７４〕に記載のオキシム化合物又はその塩。
　　〔７８〕
　Ａは、－Ｃ（Ｏ）Ｒ２を表す〔７４〕に記載のオキシム化合物又はその塩。
　　〔７９〕
　Ｒ１ａは、フェニル又は（Ｚａ）ｑａで置換されたフェニルを表す〔３〕、〔６９〕～〔７７８〕に記載のオキシム化合物又はその塩。
　　〔８０〕
　Ｒ１ａは、フェニルを表す〔７９〕に記載のオキシム化合物又はその塩。
　　〔８１〕
　Ｒ１ａは、（Ｚａ）ｑａで置換されたフェニルを表す〔７９〕に記載のオキシム化合物又はその塩。
　　〔８２〕
　Ｒ１ｂは、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表す〔３〕、〔６９〕～〔８１〕に記載のオキシム化合物又はその塩。
　　〔８３〕
　Ｒ１ｂは、Ｃ３～Ｃ８シクロアルキルを表す〔８２〕に記載のオキシム化合物又はその塩。
　　〔８４〕
　Ｒ１ｂは、Ｃ２～Ｃ６アルケニル表す〔８２〕に記載のオキシム化合物又はその塩。
　　〔８５〕
　Ｒ１ｂは、Ｃ２～Ｃ６アルキニルを表す〔８２〕に記載のオキシム化合物又はその塩。
　　〔８６〕
　Ｒ１ｂは、フェニルを表す〔８２〕に記載のオキシム化合物又はその塩。
　　〔８７〕
　Ｒ１ｂは、（Ｚｂ）ｑｂで置換されたフェニルを表す〔８２〕に記載のオキシム化合物又はその塩。
　　〔８８〕
　Ｒ２は、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、（Ｚｆ）ｑｆで置換されたフェニル又はＤ２－１０２を表す〔３〕、〔６９〕～〔８７〕に記載のオキシム化合物又はその塩。
　　〔８９〕
　Ｒ２は、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキルを表す〔８８〕に記載のオキシム化合物又はその塩。
　　〔９０〕
　Ｒ２は、（Ｚｆ）ｑｆで置換されたフェニルを表す〔８８〕に記載のオキシム化合物又はその塩。
　　〔９１〕
　Ｒ２はＤ２－１０２を表す〔８８〕に記載のオキシム化合物又はその塩。
　　〔９２〕
　Ｒ５は、－ＯＲ３１を表す〔３〕、〔６９〕～〔９１〕に記載のオキシム化合物又はその塩。
　　〔９３〕
　Ｒ５ｆは、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表す〔３〕、〔６９〕～〔９２〕に記載のオキシム化合物又はその塩。
　　〔９４〕
　Ｒ５ｆは、フェニルを表す〔９３〕に記載のオキシム化合物又はその塩。
　　〔９５〕
　Ｒ５ｆは、（Ｚｆ）ｑｆで置換されたフェニルを表す〔９３〕に記載のオキシム化合物又はその塩。
　　〔９６〕
　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表す〔３〕、〔６９〕～〔９５〕記載のオキシム化合物又はその塩。
　　〔９７〕
　Ｒ６は、Ｃ１～Ｃ６アルキルを表す〔９６〕に記載のオキシム化合物又はその塩。
　　〔９８〕
　Ｒ６は、Ｃ３～Ｃ８シクロアルキルを表す〔９６〕に記載のオキシム化合物又はその塩。
　　〔９９〕
　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニルを表す〔３〕、〔６９〕～〔９８〕に記載のオキシム化合物又はその塩。
　　〔１００〕
　Ｒ７は、水素原子を表す〔９９〕記載のオキシム化合物又はその塩。
　　〔１０１〕
　Ｒ７は、Ｃ１～Ｃ６アルキルを表す〔９９〕記載のオキシム化合物又はその塩。
　　〔１０２〕
　Ｒ７は、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキルを表す〔９９〕記載のオキシム化合物又はその塩。
　　〔１０３〕
　Ｒ７ｂは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、－ＯＲ３１ｂを表す〔３〕、〔６９〕～〔１０２〕に記載のオキシム化合物又はその塩。
　　〔１０４〕
　Ｒ７ｂは、ハロゲン原子を表す〔１０３〕記載のオキシム化合物又はその塩。
　　〔１０５〕
　Ｒ７ｂは、シアノを表す〔１０３〕記載のオキシム化合物又はその塩。
　　〔１０６〕
　Ｒ７ｂは、Ｃ３～Ｃ８シクロアルキルを表す〔１０３〕記載のオキシム化合物又はその塩。
　　〔１０７〕
　Ｒ７ｂは、－ＯＲ３１ｂを表す〔１０３〕記載のオキシム化合物又はその塩。
　　〔１０８〕
　Ｒ８ａ、Ｒ９ａ、Ｒ１０、Ｒ１１及びＲ１２は、水素原子を表す〔３〕、〔６９〕～〔１０７〕に記載のオキシム化合物又はその塩。
　　〔１０９〕
　Ｒ３１は、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル又は－Ｃ（Ｏ）Ｒ３７を表す〔３〕、〔６９〕～〔１０８〕に記載のオキシム化合物又はその塩。
　　〔１１０〕
　Ｒ３１は、Ｃ１～Ｃ６アルキルを表す〔１０９〕に記載のオキシム化合物又はその塩。
　　〔１１１〕
　Ｒ３１は、Ｃ３～Ｃ８シクロアルキルを表す〔１０９〕に記載のオキシム化合物又はその塩。
　　〔１１２〕
　Ｒ３１は、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキルを表す〔１０９〕に記載のオキシム化合物又はその塩。
　　〔１１３〕
　Ｒ３１は、－Ｃ（Ｏ）Ｒ３７を表す〔１０９〕に記載のオキシム化合物又はその塩。
　　〔１１４〕
　Ｒ３１ｂは、水素原子又はＣ１～Ｃ６アルキルを表す〔３〕、〔６９〕～〔１１３〕に記載のオキシム化合物又はその塩。
　　〔１１５〕
　Ｒ３７は、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ３～Ｃ８シクロアルキルオキシ又はフェニルを表す３〕、〔６９〕～〔１１４〕に記載のオキシム化合物又はその塩。
　　〔１１６〕
　Ｒ３７は、Ｃ１～Ｃ６アルキルを表す〔１１５〕に記載のオキシム化合物又はその塩。
　　〔１１７〕
　Ｒ３７は、Ｃ１～Ｃ６アルコキシを表す〔１１５〕に記載のオキシム化合物又はその塩。
　　〔１１８〕
　Ｒ３７は、Ｃ３～Ｃ８シクロアルキルオキシを表す〔１１５〕に記載のオキシム化合物又はその塩。
　　〔１１９〕
　Ｒ３７は、フェニルを表す〔１１５〕に記載のオキシム化合物又はその塩。
　　〔１２０〕
　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表す〔３〕、〔６９〕～〔１１９〕に記載のオキシム化合物又はその塩。
　　〔１２１〕
　Ｚ４は、ハロゲン原子を表す〔１２０〕記載のオキシム化合物又はその塩。
　　〔１２２〕
　Ｚ４は、Ｃ１～Ｃ６アルキルを表す〔１２０〕記載のオキシム化合物又はその塩。
　　〔１２３〕
　Ｚ４は、Ｃ３～Ｃ８シクロアルキルを表す〔１２０〕記載のオキシム化合物又はその塩。
　　〔１２４〕
　Ｚ４は、Ｃ１～Ｃ６アルコキシを表す〔１２０〕記載のオキシム化合物又はその塩。
　　〔１２５〕
　Ｚ６は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表す〔３〕、〔６９〕～〔１２４〕に記載のオキシム化合物又はその塩。
　　〔１２６〕
　Ｚ６は、水素原子を表す〔１２５〕記載のオキシム化合物又はその塩。
　　〔１２７〕
　Ｚ６は、ハロゲン原子を表す〔１２５〕記載のオキシム化合物又はその塩。
　　〔１２８〕
　Ｚ６は、Ｃ１～Ｃ６アルキルを表す〔１２５〕記載のオキシム化合物又はその塩。
　　〔１２９〕
　Ｚ７は、－ＯＲ４１を表す〔３〕、〔６９〕～〔１２８〕に記載のオキシム化合物又はその塩。
　　〔１３０〕
　Ｚ８は、水素原子又はＣ１～Ｃ６アルキルを表す〔３〕、〔６９〕～〔１２９〕に記載のオキシム化合物又はその塩。
　　〔１３１〕
　Ｚ８は、水素原子を表す〔１３０〕記載のオキシム化合物又はその塩。
　　〔１３２〕
　Ｚ８は、Ｃ１～Ｃ６アルキルを表す〔１３０〕記載のオキシム化合物又はその塩。
　　〔１３３〕
　Ｚａは、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシを表す〔３〕、〔６９〕～〔１３２〕に記載のオキシム化合物又はその塩。
　　〔１３４〕
　Ｚａは、ハロゲン原子を表す〔１３３〕に記載のオキシム化合物又はその塩。
　　〔１３５〕
　Ｚａは、Ｃ１～Ｃ６アルキルを表す〔１３３〕に記載のオキシム化合物又はその塩。
　　〔１３６〕
　Ｚａは、Ｃ１～Ｃ６アルコキシを表す〔１３３〕に記載のオキシム化合物又はその塩。
　　〔１３７〕
　Ｚｂは、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシを表す〔３〕、〔６９〕～〔１３６〕に記載のオキシム化合物又はその塩。
　　〔１３８〕
　Ｚｂは、ハロゲン原子を表す〔１３７〕に記載のオキシム化合物又はその塩。
　　〔１３９〕
　Ｚｂは、Ｃ１～Ｃ６アルキルを表す〔１３７〕に記載のオキシム化合物又はその塩。
　　〔１４０〕
　Ｚｂは、Ｃ１～Ｃ６アルコキシを表す〔１３７〕に記載のオキシム化合物又はその塩。
　　〔１４１〕
　Ｚｆは、ハロゲン原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシを表す〔３〕、〔６９〕～〔１４０〕に記載のオキシム化合物又はその塩。
　　〔１４２〕
　Ｚｆは、ハロゲン原子を表す〔１４１〕に記載のオキシム化合物又はその塩。
　　〔１４３〕
　Ｚｆは、Ｃ１～Ｃ６アルキルを表す〔１４１〕に記載のオキシム化合物又はその塩。
　　〔１４４〕
　Ｚｆは、Ｃ１～Ｃ６アルコキシを表す〔１４１〕に記載のオキシム化合物又はその塩。
　　〔１４５〕
　Ａは、水素原子、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ２を表し、
　Ｒ２は、Ｃ１～Ｃ６アルキル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
　Ｒ６は、Ｃ１～Ｃ６アルキルを表し、
　Ｒ７は、Ｃ１～Ｃ６アルキルを表し、
　Ｚ７は、－Ｓ（Ｏ）ｒＲ４１を表し、
　Ｚ４は、Ｃ１～Ｃ６アルコキシを表し、
　Ｒ４１は、Ｄ３－６０ｂを表し、
　Ｚ６及びＺ８は、水素原子を表し、
　Ｘ３は、ハロゲン原子を表し、
　Ｚｆは、ハロゲン原子を表し、
　ｑｆは、１又は２の整数を表し、
　ｔ５は、１の整数を表す〔７３〕に記載のオキシム化合物又はその塩。
　　〔１４６〕
　式（３）：
Figure JPOXMLDOC01-appb-C000012
 ［式中、Ｑは、ＮＯＲ７を表し、
　Ａは、Ｃ１～Ｃ６アルキルを表し、
　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
　Ｒ７は、Ｃ１～Ｃ６アルキルを表し、
　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、水素原子を表し、
　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
　Ｚ５は、水素原子を表し、
　Ｚ６及びＺ８は、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
　Ｘ３ａは、Ｃ１～Ｃ６アルキルを表し、
　ｍは、１の整数を表し、
　ｎは、０の整数を表し、
　ｔ４は、４の整数を表す］で表される〔１〕乃至〔１４５〕のいずれか一項に記載の化合物の製造中間体。
　　〔１４７〕
　〔１〕乃至〔１４５〕のいずれか一項に記載のケトン及びオキシム化合物並びにそれらの塩から選ばれる１種又は２種以上を有効成分として含有する農薬。
　　〔１４８〕
　〔１〕乃至〔１４５〕のいずれか一項に記載のケトン及びオキシム化合物並びにそれらの塩から選ばれる１種又は２種以上を有効成分として含有する除草剤。 As a result of intensive research aimed at solving the above problems, the present inventors have found that the novel ketone or oxime compound represented by the following formula (1) according to the present invention has excellent herbicidal activity and target. The present invention has been completed by discovering that it is a highly useful compound that has a high safety against certain crops and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects.
That is, the present invention relates to the following [1] to [148].
[1]
Formula (1):
Figure JPOXMLDOC01-appb-C000007
 [Wherein B represents a ring represented by either B-1 or B-2;
Figure JPOXMLDOC01-appb-C000008
 Q is an oxygen atom, sulfur atom or NOR 7 Represents
A is a hydrogen atom, C 1 ~ C 6 Alkyl, R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -C (S) R 2 , -P (O) (OR 3c ) 2 Or -P (S) (OR 3c ) 2 Represents
R 1a Is C 1 ~ C 8 Alkyl, R 5a Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5a Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5a Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5a Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5a Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 4b ) R 3b , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
R 1b , R 1c , R 1d And R 1e Are each independently C 1 ~ C 8 Alkyl, R 5b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5b Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 2 Is a hydrogen atom, C 1 ~ C 8 Alkyl, R 5f Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5f Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5f Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5f Optionally substituted with (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkylcarbonyl, benzoyl, (Z f ) qf Benzoyl, phenyl, (Z f ) qf Substituted with phenyl, -N (R 4a ) R 3a , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
D2-1 to D2-56, D2-100, D2-100 to D2-106, and D2-107 each represent a ring represented by the following structure:
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000010
 R 3a , R 3b , R 4a And R 4b Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 5g Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5g Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5g Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5g Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5g Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 3c Is C 1 ~ C 6 Represents alkyl or phenyl,
R 5 Is a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, —C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, -OR 31 , -S (O) r2 R 31 , Benzoyl, (Z f ) qf Benzoyl, phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 5a , R 5b And R 5g Each independently represents a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 1 ~ C 6 Alkoxy, phenyl, (Z b ) qb Phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 5f Is a halogen atom, cyano, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, —C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -OR f , -S (O) r2 R f , -N (R 4f ) R 3f , Phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 6 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 6b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 6b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 6b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 6b Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 6b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z j ) qj Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 6b Is a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, -OR 31b , -S (O) r1 R 31b , C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, phenyl, (Z j ) qj Phenyl, benzoyl, substituted with (Z j ) qj Represents benzoyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107 substituted with
R 7 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 7b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 7b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 7b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 7b Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 7b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, -S (O) r1 R 15a , -C (O) OR 15b , -C (S) OR 15b , -C (O) SR 15b , -C (S) SR 15b , -C (O) R 16 , -C (S) R 16 , -P (O) (OR 17c ) 2 , -P (S) (OR 17c ) 2 , Phenyl, (Z j ) qj Phenyl, D2-1, D2-2, D2-4 to D2-6, D2-8 to D2-10, D2-12 to D2-19, D2-21, D2-23, D2-25, D2-27, D2-30 to D2-55 or D2-56
R 7b Is a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, -OR 31b , -S (O) r1 R 31b , -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, phenyl, (Z j ) qj Phenyl, benzoyl, substituted with (Z j ) qj Represents benzoyl, D2-1 to D2-56, D2-100, D2-101 to D2-106 or D2-107, substituted with
R 8a , R 8b , R 9a , R 9b , R 10 , R 11 And R 12 Each independently represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, -OH, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, phenyl, (Z j ) qj Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 15a Is C 1 ~ C 8 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 18 ) R 17 , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
R 15b Are each independently C 1 ~ C 8 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 16 Is a hydrogen atom, C 1 ~ C 8 Alkyl, R 20f Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20f Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20f Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20f Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20f Optionally substituted with (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkylcarbonyl, benzoyl, (Z f ) qf Benzoyl, phenyl, (Z f ) qf Substituted with phenyl, -N (R 18 ) R 17 , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
R 17 And R 18 Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 17c Is C 1 ~ C 6 Represents alkyl or phenyl,
R 20 Each independently represents a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 1 ~ C 6 Alkoxy, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 20f Is a halogen atom, cyano, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, —C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -OR f , -S (O) r1 R f , -N (R 4f ) R 3f , Phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
R 31 Is a hydrogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl, —C (O) R 37 , Phenyl or (Z f ) qf Represents phenyl substituted with
R 31b Is a hydrogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl, —C (O) R 37 , Phenyl or (Z i ) qi Represents phenyl substituted with
R 37 Is C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy, C 3 ~ C 8 Cycloalkyloxy, phenyl or (Z f ) qf Represents phenyl substituted with
R f Is a hydrogen atom, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, phenyl (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkylcarbonyl, phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100, D2-101 to D2-106 or D2-107 substituted with
R 3f And R 4f Are each independently C 1 ~ C 6 Represents alkyl or benzoyl,
Z 4 Is a hydrogen atom, halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylthio, halo (C 1 ~ C 6 ) Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfonyl or -NH 2 Represents
Z 5 , Z 6 And Z 8 Each independently represents a hydrogen atom, a halogen atom, or C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 Represents alkoxy,
Z 7 Is -OR 41 Or -S (O) r R 41 Represents
R 41 Are D3-1a, D3-1b, D3-2a, D3-2b, D3-3a, D3-3b, D3-4a, D3-4b, D3-18a, D3-18b, D3-21a, D3-21b, D3-27a, D3-27b, D3-32a, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-58b, D3-59a, D3-60a, D3- 60b or D3-65a,
D3-1a, D3-1b, D3-2a, D3-2b, D3-3a, D3-3b, D3-4a, D3-4b, D3-18a, D3-18b, D3-21a, D3-21b, D3- 27a, D3-27b, D3-32a, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-58b, D3-59a, D3-60a, D3-60b and D3-65a represents a ring represented by the following structure:
Figure JPOXMLDOC01-appb-C000011
 X 2 Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 X represents alkylcarbonylamino or phenyl, and when f2, f3, f4, f5, f7, f8, f9, f10 or f11 represents an integer of 2 or more, each X 2 May be the same as or different from each other, and two X 2 Are adjacent, the two adjacent X 2 Form -CH = CHCH = CH- 2 A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom or C 1 ~ C 6 Optionally substituted by alkyl,
X 3 Is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, C 1 ~ C 6 Represents alkoxycarbonyl or phenyl, and when t2, t3, t4 or t5 represents an integer of 2 or more, each X 3 May be the same or different from each other,
X 2a And X 4 Each independently represents a hydrogen atom, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkylcarbonyl, C 1 ~ C 6 Represents alkoxycarbonyl or phenyl,
Z a Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 When Z represents an alkylcarbonylamino or phenyl and qa represents an integer of 2 or more, each Z a May be the same as or different from each other, and two Z a Are adjacent to each other, two adjacent Z a Form -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- By doing each Z a A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl or C 1 ~ C 6 Optionally substituted by alkylsulfonyl,
Z b Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 When Z represents an alkylcarbonylamino or phenyl and qb represents an integer of 2 or more, each Z b May be the same or different from each other,
Z f Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 Alkylcarbonylamino, -OR 51 , -S (O) r2 R 51 Or phenyl, and when qf represents an integer of 2 or more, each Z f May be the same as or different from each other, and two Z f Are adjacent to each other, two adjacent Z f Form -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- By doing each Z f A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl or C 1 ~ C 6 Optionally substituted by alkylsulfonyl,
Z j Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 When Z represents an alkylcarbonylamino or phenyl and qj represents an integer of 2 or more, each Z j May be the same as or different from each other, and two Z j Are adjacent to each other, two adjacent Z j Form -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- By doing each Z j A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl or C 1 ~ C 6 Optionally substituted by alkylsulfonyl,
R 51 Is C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, phenyl (C 1 ~ C 6 ) Represents alkyl or phenyl,
f1, p1, p2 and t1 each independently represents an integer of 0 or 1,
f2, r, r1, r2 and t2 each independently represent an integer of 0, 1 or 2;
m, n, f3 and t3 each independently represent an integer of 0, 1, 2 or 3;
f4 and t4 each independently represents an integer of 0, 1, 2, 3 or 4;
f5 and t5 each independently represent an integer of 0, 1, 2, 3, 4 or 5;
qa, qb, qf and qj each independently represent an integer of 1, 2, 3, 4 or 5;
f6 represents an integer of 0, 1, 2, 3, 4, 5 or 6,
f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
f8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
f10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
f11 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11,
f12 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12. Or a salt thereof.
[2]
Q is the ketone compound or salt thereof according to [1], wherein Q represents an oxygen atom.
[3]
Q is NOR 7 The oxime compound or salt thereof according to [1], wherein
[4]
R 8a , R 8b , R 9a And R 9b Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ~ C 6 Alkyl, —OH, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl or di (C 1 ~ C 6 ) Represents alkylaminocarbonyl,
R 10 , R 11 And R 12 Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ~ C 6 Alkyl, —OH, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkoxycarbonyl or C 1 ~ C 6 The ketone compound or a salt thereof according to [2], which represents alkylcarbonyl.
[5]
R 6 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 6b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 6b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, phenyl, (Z j ) qj The ketone compound or the salt thereof according to [4], which represents phenyl, D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38, substituted by:
[6]
R 8a , R 8b , R 9a And R 9b Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 Represents alkoxycarbonyl,
R 10 , R 11 And R 12 Each independently represents a hydrogen atom or C 1 ~ C 6 Represents alkyl,
Z 5 Is a ketone compound or a salt thereof according to [5], which represents a hydrogen atom.
[7]
A is a hydrogen atom, C 1 ~ C 6 Alkyl, R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -P (O) (OR 3c ) 2 Or -P (S) (OR 3c ) 2 Represents
R 1a Is C 1 ~ C 8 Alkyl, R 5a Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5a Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 4b ) R 3b D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55, D2-56, D2-100 to D2 -104 or D2-105,
R 1b , R 1c , R 1d And R 1e Are each independently C 1 ~ C 8 Alkyl, R 5b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl, (Z b ) qb Phenyl, D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55 or D2-56 substituted with Represent,
R 3a , R 3b , R 4a And R 4b Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 5g Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl or (Z b ) qb The ketone compound or a salt thereof according to [6], which represents phenyl substituted with.
[8]
B represents B-1,
A represents a hydrogen atom,
R 6 Is C 1 ~ C 6 Alkyl or C 3 ~ C 8 Represents cycloalkyl,
R 8a , R 9a , R 10 , R 11 And R 12 Represents a hydrogen atom,
Z 4 Is a halogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 Represents alkoxy,
Z 6 Is a hydrogen atom, a halogen atom or C 1 ~ C 6 Represents alkyl,
Z 8 Is a hydrogen atom or C 1 ~ C 6 Represents alkyl,
R 41 Represents D3-58a or D3-60b
X 3 Is a halogen atom, C 1 ~ C 6 Alkyl or halo (C 1 ~ C 6 ) Represents alkyl, and when t5 represents an integer of 2, each X 3 May be the same or different from each other,
n and r represent 0;
m and t3 represent an integer of 1;
t5 represents the integer of 1 or 2, The ketone compound or its salt of [7] description.
[9]
A is R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, -S (O) r2 R 1a , -C (O) OR 1b Or -C (O) R 2 [2], the ketone compound according to [4] to [8], or a salt thereof.
[10]
A is R 5 Optionally substituted with (C 1 ~ C 6 ) The ketone compound or salt thereof according to [9], which represents alkyl.
[11]
A is -S (O) r2 R 1a [9] represents a ketone compound or a salt thereof.
[12]
A is -C (O) OR 1b [9] represents a ketone compound or a salt thereof.
[13]
A is —C (O) R 2 [9] represents a ketone compound or a salt thereof.
[14]
R 1a Is phenyl or (Z a ) qa The ketone compound or a salt thereof according to [2], [4] to [13], which represents phenyl substituted with
[15]
R 1a Represents a ketone compound or a salt thereof according to [14], which represents phenyl.
[16]
R 1a (Z a ) qa The ketone compound or a salt thereof according to [14], which represents phenyl substituted with
[17]
R 1b Is C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl or (Z b ) qb The ketone compound or a salt thereof according to [2], [4] to [16], which represents phenyl substituted with
[18]
R 1b Is C 3 ~ C 8 The ketone compound or a salt thereof according to [17], which represents cycloalkyl.
[19]
R 1b Is C 2 ~ C 6 The ketone compound or a salt thereof according to [17], which represents alkenyl.
[20]
R 1b Is C 2 ~ C 6 The ketone compound or a salt thereof according to [17], which represents alkynyl.
[21]
R 1b Represents a ketone compound or a salt thereof according to [17], which represents phenyl.
[22]
R 1b (Z b ) qb The ketone compound or a salt thereof according to [17], which represents phenyl substituted with
[23]
R 2 Is R 5f Optionally substituted with (C 1 ~ C 6 ) Alkyl, (Z f ) qf The ketone compound or the salt thereof according to [2], [4] to [22], which represents phenyl substituted with or D2-102.
[24]
R 2 Is R 5f Optionally substituted with (C 1 ~ C 6 ) The ketone compound or salt thereof according to [23], which represents alkyl.
[25]
R 2 (Z f ) qf The ketone compound or a salt thereof according to [23], which represents phenyl substituted with
[26]
R 2 Is a ketone compound or a salt thereof according to [23], which represents D2-102.
[27]
R 5 Is -OR 31 [2], the ketone compound according to [4] to [26], or a salt thereof.
[28]
R 5f Is phenyl or (Z f ) qf The ketone compound or salt thereof according to [2], [4] to [27], which represents phenyl substituted with
[29]
R 5f Represents a ketone compound or a salt thereof according to [28], which represents phenyl.
[30]
R 5f (Z f ) qf The ketone compound or a salt thereof according to [28], which represents phenyl substituted with
[31]
R 6 Is C 1 ~ C 6 Alkyl or C 3 ~ C 8 The ketone compound or salt thereof according to [2], [4] to [30], which represents cycloalkyl.
[32]
R 6 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [31], which represents alkyl.
[33]
R 6 Is C 3 ~ C 8 The ketone compound or a salt thereof according to [31], which represents cycloalkyl.
[34]
R 8a , R 9a , R 10 , R 11 And R 12 Is a ketone compound or a salt thereof according to [2], [4] to [33], which represents a hydrogen atom.
[35]
R 31 Is C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl or —C (O) R 37 [2], the ketone compound according to [4] to [34] or a salt thereof.
[36]
R 31 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [35], which represents alkyl.
[37]
R 31 Is C 3 ~ C 8 The ketone compound or a salt thereof according to [35], which represents cycloalkyl.
[38]
R 31 Is C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) The ketone compound or salt thereof according to [35], which represents alkyl.
[39]
R 31 Is -C (O) R 37 [35] represents a ketone compound or a salt thereof.
[40]
R 37 Is C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy, C 3 ~ C 8 The ketone compound or salt thereof according to [2], [4] to [39], which represents cycloalkyloxy or phenyl.
[41]
R 37 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [40], which represents alkyl.
[42]
R 37 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [40], which represents alkoxy.
[43]
R 37 Is C 3 ~ C 8 The ketone compound or a salt thereof according to [40], which represents cycloalkyloxy.
[44]
R 37 Represents a ketone compound or a salt thereof according to [40], which represents phenyl.
[45]
Z 4 Is a halogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 The ketone compound or salt thereof according to [2], [4] to [44], which represents alkoxy.
[46]
Z 4 Represents a ketone compound or a salt thereof according to [45], which represents a halogen atom.
[47]
Z 4 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [45], which represents alkyl.
[48]
Z 4 Is C 3 ~ C 8 The ketone compound or a salt thereof according to [45], which represents cycloalkyl.
[49]
Z 4 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [45], which represents alkoxy.
[50]
Z 6 Is a hydrogen atom, a halogen atom or C 1 ~ C 6 The ketone compound or salt thereof according to [2], [4] to [49], which represents alkyl.
[51]
Z 6 Represents a ketone compound or a salt thereof according to [50], which represents a hydrogen atom.
[52]
Z 6 Represents a ketone compound or a salt thereof according to [50], which represents a halogen atom.
[53]
Z 6 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [50], which represents alkyl.
[54]
Z 8 Is a hydrogen atom or C 1 ~ C 6 The ketone compound or salt thereof according to [2], [4] to [53], which represents alkyl.
[55]
Z 8 Represents a ketone compound or a salt thereof according to [54], which represents a hydrogen atom.
[56]
Z 8 Is C 1 ~ C 6 The ketone compound or a salt thereof according to [54], which represents alkyl.
[57]
Z a Is a halogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 The ketone compound or salt thereof according to [2], [4] to [56], which represents alkoxy.
[58]
Z a Represents a ketone compound or a salt thereof according to [57], which represents a halogen atom.
[59]
Z a Is C 1 ~ C 6 The ketone compound or a salt thereof according to [57], which represents alkyl.
[60]
Z a Is C 1 ~ C 6 The ketone compound or a salt thereof according to [57], which represents alkoxy.
[61]
Z b Is a halogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 The ketone compound or salt thereof according to [2], [4] to [60], which represents alkoxy.
[62]
Z b Represents a ketone compound or a salt thereof according to [61], which represents a halogen atom.
[63]
Z b Is C 1 ~ C 6 The ketone compound or a salt thereof according to [61], which represents alkyl.
[64]
Z b Is C 1 ~ C 6 The ketone compound or a salt thereof according to [61], which represents alkoxy.
[65]
Z f Is a halogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 The ketone compound or salt thereof according to [2], [4] to [64], which represents alkoxy.
[66]
Z f Represents a ketone compound or a salt thereof according to [65], which represents a halogen atom.
[67]
Z f Is C 1 ~ C 6 The ketone compound or a salt thereof according to [65], which represents alkyl.
[68]
Z f Is C 1 ~ C 6 The ketone compound or a salt thereof according to [65], which represents alkoxy.
[69]
R 8a , R 8b , R 9a And R 9b Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ~ C 6 Alkyl, —OH, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl or di (C 1 ~ C 6 ) Represents alkylaminocarbonyl,
R 10 , R 11 And R 12 Each independently represents a hydrogen atom, a halogen atom, cyano, C 1 ~ C 6 Alkyl, —OH, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkoxycarbonyl or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], which represents alkylcarbonyl.
[70]
R 6 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 6b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 6b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, phenyl, (Z j ) qj Represents phenyl, D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38, substituted with
R 7 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 7b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 2 ~ C 6 Alkenyl, R 7b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, R 7b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, -S (O) r1 R 15a , -C (O) OR 15b , -C (S) OR 15b , -C (O) SR 15b , -C (S) SR 15b , -C (O) R 16 , -P (O) (OR 17c ) 2 Or -P (S) (OR 17c ) 2 [69] The oxime compound or a salt thereof according to [69].
[71]
R 8a , R 8b , R 9a And R 9b Are each independently a hydrogen atom, C 1 ~ C 8 Alkyl or C 1 ~ C 6 Represents alkoxycarbonyl,
R 10 , R 11 And R 12 Each independently represents a hydrogen atom or C 1 ~ C 6 Alkyl represents a table,
Z 5 Represents an oxime compound or a salt thereof according to [70], which represents a hydrogen atom.
[72]
A is a hydrogen atom, C 1 ~ C 6 Alkyl, R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -P (O) (OR 3c ) 2 Or -P (S) (OR 3c ) 2 Represents
R 1a Is C 1 ~ C 8 Alkyl, R 5a Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5a Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 4b ) R 3b D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55, D2-56, D2-100 to D2 -104 or D2-105,
R 1b , R 1c , R 1d And R 1e Are each independently C 1 ~ C 8 Alkyl, R 5b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl, (Z b ) qb Phenyl, D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55 or D2-56 substituted with Represent,
R 3a , R 3b , R 4a And R 4b Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 5g Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl or (Z b ) qb Represents phenyl substituted with
R 15a Is C 1 ~ C 8 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 18 ) R 17 D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55, D2-56, D2-100 to D2 -104 or D2-105,
R 15b Is C 1 ~ C 8 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl, (Z b ) qb Phenyl, D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55 or D2-56 substituted with Represent,
R 17 And R 18 Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl or (Z b ) qb The oxime compound or a salt thereof according to [71], which represents phenyl substituted with:
[73]
B represents B-1,
A is a hydrogen atom, C 1 ~ C 6 Alkyl, R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e Or -C (O) R 2 Represents
R 1a Is C 1 ~ C 6 Alkyl, R 5a Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 4b ) R 3b Or D2-101,
R 1b Is C 1 ~ C 6 Alkyl, R 5b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, phenyl or (Z b ) qb Represents phenyl substituted with
R 1c Represents phenyl or D2-56;
R 1d Is C 1 ~ C 6 Represents alkyl,
R 1e Represents phenyl,
R 2 Is C 1 ~ C 6 Alkyl, R 5f Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, phenyl, (Z f ) qf Substituted with phenyl, quinolin-8-yl, —N (R 4a ) R 3a , D2-1, D2-34, D2-100 or D2-102,
R 3a And R 4a Are each independently C 1 ~ C 6 Represents alkyl,
R 3b And R 4b Are each independently C 1 ~ C 6 Represents alkyl,
R 5 Is -OR 31 , Phenyl or (Z f ) qf Represents phenyl substituted with
R 5a Represents a halogen atom,
R 5b Is a halogen atom, C 1 ~ C 6 Represents alkoxy or phenyl,
R 5f Is a halogen atom, -OR f , -S (O) r2 R f , Phenyl or (Z f ) qf Represents phenyl substituted with
R 6 Is C 1 ~ C 6 Alkyl or C 3 ~ C 8 Represents cycloalkyl,
R 7 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 7b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, -S (O) r1 R 15a , -C (O) OR 15b Or -C (O) R 16 Represents
R 7b Is a halogen atom, cyano, C 3 ~ C 8 Cycloalkyl, -OR 31b , Phenyl, (Z j ) qj Represents phenyl substituted with
R 8a , R 9a , R 10 , R 11 And R 12 Represents a hydrogen atom,
R 15a Is C 1 ~ C 6 Represents alkyl,
R 15b Is C 1 ~ C 6 Represents alkyl,
R 16 Is C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or —N (R 18 ) R 17 Represents
R 17 Is C 1 ~ C 6 Represents alkyl,
R 18 Represents a hydrogen atom,
R 31 Is C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl or —C (O) R 37 Represents
R 31b Is a hydrogen atom or C 1 ~ C 6 Represents alkyl,
R 37 Is C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy, C 3 ~ C 8 Represents cycloalkyloxy or phenyl,
R f Is C 1 ~ C 6 Alkyl, phenyl or (Z f ) qf Represents phenyl substituted with
Z 4 Is a halogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 Represents alkoxy,
R 41 D3-3a, D3-18b, D3-21a, D3-21b, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-60a or D3-60b Represent,
Z 6 Is a hydrogen atom, a halogen atom or C 1 ~ C 6 Represents alkyl,
Z 8 Is a hydrogen atom or C 1 ~ C 6 Represents alkyl,
X 3 Is a halogen atom, nitro, cyano, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy or C 1 ~ C 6 Represents alkoxycarbonyl, and when t2, t3, t4 or t5 represents an integer of 2 or more, each X 3 May be the same or different from each other,
Z a Is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy or C 1 ~ C 6 When alkylcarbonylamino is represented and qa represents an integer of 2 or more, each Z a May be the same or different from each other,
Z b Is a halogen atom, C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy or C 1 ~ C 6 Represents alkoxycarbonyl,
Z f Is a halogen atom, nitro, cyano, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio or C 1 ~ C 6 Represents alkoxycarbonyl, and when qf represents an integer of 2 or more, each Z f May be the same or different from each other,
Z j Represents a halogen atom,
f3, f4, f7, f8, f10, n and p2 represent 0;
m, qb, qj, t2 and t4 represent an integer of 1;
t5 and r each independently represents an integer of 0, 1 or 2;
t3 represents an integer of 1 or 2
qa and qf each independently represent an integer of 1, 2 or 3,
r1 represents an integer of 2;
r2 represents the integer of 0 or 2, The oxime compound or a salt thereof according to [72].
[74]
A is R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, -S (O) r2 R 1a , -C (O) OR 1b Or -C (O) R 2 The oxime compound or a salt thereof according to any one of [3] and [69] to [73].
[75]
A is R 5 Optionally substituted with (C 1 ~ C 6 ) The oxime compound or a salt thereof according to [74], which represents alkyl.
[76]
A is -S (O) r2 R 1a The oxime compound or a salt thereof according to [74].
[77]
A is -C (O) OR 1b The oxime compound or a salt thereof according to [74].
[78]
A is —C (O) R 2 The oxime compound or a salt thereof according to [74].
[79]
R 1a Is phenyl or (Z a ) qa The oxime compound or a salt thereof according to [3], [69] to [778], which represents phenyl substituted with
[80]
R 1a Represents an oxime compound or a salt thereof according to [79], which represents phenyl.
[81]
R 1a (Z a ) qa The oxime compound or a salt thereof according to [79], which represents phenyl substituted with
[82]
R 1b Is C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, phenyl or (Z b ) qb The oxime compound or a salt thereof according to [3], [69] to [81], which represents phenyl substituted with
[83]
R 1b Is C 3 ~ C 8 The oxime compound or a salt thereof according to [82], which represents cycloalkyl.
[84]
R 1b Is C 2 ~ C 6 The oxime compound or a salt thereof according to [82], which represents alkenyl.
[85]
R 1b Is C 2 ~ C 6 The oxime compound or a salt thereof according to [82], which represents alkynyl.
[86]
R 1b Represents an oxime compound or a salt thereof according to [82], which represents phenyl.
[87]
R 1b (Z b ) qb The oxime compound or a salt thereof according to [82], which represents phenyl substituted with
[88]
R 2 Is R 5f Optionally substituted with (C 1 ~ C 6 ) Alkyl, (Z f ) qf The oxime compound or a salt thereof according to [3], [69] to [87], which represents phenyl substituted with or D2-102.
[89]
R 2 Is R 5f Optionally substituted with (C 1 ~ C 6 ) The oxime compound or a salt thereof according to [88], which represents alkyl.
[90]
R 2 (Z f ) qf The oxime compound or a salt thereof according to [88], which represents phenyl substituted with
[91]
R 2 Is an oxime compound or a salt thereof according to [88], which represents D2-102.
[92]
R 5 Is -OR 31 The oxime compound or a salt thereof according to any one of [3] and [69] to [91].
[93]
R 5f Is phenyl or (Z f ) qf The oxime compound or a salt thereof according to [3], [69] to [92], which represents phenyl substituted with
[94]
R 5f Is an oxime compound or a salt thereof according to [93], which represents phenyl.
[95]
R 5f (Z f ) qf The oxime compound or a salt thereof according to [93], which represents phenyl substituted with:
[96]
R 6 Is C 1 ~ C 6 Alkyl or C 3 ~ C 8 The oxime compound or a salt thereof according to [3], [69] to [95], which represents cycloalkyl.
[97]
R 6 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [96], which represents alkyl.
[98]
R 6 Is C 3 ~ C 8 The oxime compound or a salt thereof according to [96], which represents cycloalkyl.
[99]
R 7 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 7b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [98], which represents alkynyl.
[100]
R 7 Represents an oxime compound or a salt thereof according to [99], which represents a hydrogen atom.
[101]
R 7 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [99], which represents alkyl.
[102]
R 7 Is R 7b Optionally substituted with (C 1 ~ C 6 ) The oxime compound or a salt thereof according to [99], which represents alkyl.
[103]
R 7b Is a halogen atom, cyano, C 3 ~ C 8 Cycloalkyl, -OR 31b The oxime compound or a salt thereof according to any one of [3] and [69] to [102].
[104]
R 7b Represents an oxime compound or a salt thereof according to [103], which represents a halogen atom.
[105]
R 7b Represents an oxime compound or a salt thereof according to [103], which represents cyano.
[106]
R 7b Is C 3 ~ C 8 The oxime compound or a salt thereof according to [103], which represents cycloalkyl.
[107]
R 7b Is -OR 31b [103] The oxime compound or a salt thereof according to [103].
[108]
R 8a , R 9a , R 10 , R 11 And R 12 Represents an oxime compound or a salt thereof according to [3], [69] to [107], which represents a hydrogen atom.
[109]
R 31 Is C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl or —C (O) R 37 The oxime compound or a salt thereof according to any one of [3] and [69] to [108].
[110]
R 31 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [109], which represents alkyl.
[111]
R 31 Is C 3 ~ C 8 The oxime compound or a salt thereof according to [109], which represents cycloalkyl.
[112]
R 31 Is C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) The oxime compound or a salt thereof according to [109], which represents alkyl.
[113]
R 31 Is -C (O) R 37 The oxime compound or a salt thereof according to [109], wherein
[114]
R 31b Is a hydrogen atom or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [113], which represents alkyl.
[115]
R 37 Is C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy, C 3 ~ C 8 The oxime compound or salt thereof according to 3], [69] to [114], which represents cycloalkyloxy or phenyl.
[116]
R 37 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [115], which represents alkyl.
[117]
R 37 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [115], which represents alkoxy.
[118]
R 37 Is C 3 ~ C 8 The oxime compound or a salt thereof according to [115], which represents cycloalkyloxy.
[119]
R 37 Is an oxime compound or a salt thereof according to [115], which represents phenyl.
[120]
Z 4 Is a halogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [119], which represents alkoxy.
[121]
Z 4 Represents an oxime compound or a salt thereof according to [120], which represents a halogen atom.
[122]
Z 4 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [120], which represents alkyl.
[123]
Z 4 Is C 3 ~ C 8 The oxime compound or a salt thereof according to [120], which represents cycloalkyl.
[124]
Z 4 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [120], which represents alkoxy.
[125]
Z 6 Is a hydrogen atom, a halogen atom or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [124], which represents alkyl.
[126]
Z 6 Represents an oxime compound or a salt thereof according to [125], which represents a hydrogen atom.
[127]
Z 6 Represents an oxime compound or a salt thereof according to [125], which represents a halogen atom.
[128]
Z 6 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [125], which represents alkyl.
[129]
Z 7 Is -OR 41 The oxime compound or salt thereof according to [3], [69] to [128], wherein
[130]
Z 8 Is a hydrogen atom or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [129], which represents alkyl.
[131]
Z 8 Represents an oxime compound or a salt thereof according to [130], which represents a hydrogen atom.
[132]
Z 8 Is C 1 ~ C 6 The oxime compound or a salt thereof according to [130], which represents alkyl.
[133]
Z a Is a halogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [132], which represents alkoxy.
[134]
Z a Represents an oxime compound or a salt thereof according to [133], which represents a halogen atom.
[135]
Z a Is C 1 ~ C 6 The oxime compound or a salt thereof according to [133], which represents alkyl.
[136]
Z a Is C 1 ~ C 6 The oxime compound or a salt thereof according to [133], which represents alkoxy.
[137]
Z b Is a halogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [136], which represents alkoxy.
[138]
Z b Represents an oxime compound or a salt thereof according to [137], which represents a halogen atom.
[139]
Z b Is C 1 ~ C 6 The oxime compound or a salt thereof according to [137], which represents alkyl.
[140]
Z b Is C 1 ~ C 6 The oxime compound or a salt thereof according to [137], which represents alkoxy.
[141]
Z f Is a halogen atom, C 1 ~ C 6 Alkyl or C 1 ~ C 6 The oxime compound or a salt thereof according to [3], [69] to [140], which represents alkoxy.
[142]
Z f Represents an oxime compound or a salt thereof according to [141], which represents a halogen atom.
[143]
Z f Is C 1 ~ C 6 The oxime compound or a salt thereof according to [141], which represents alkyl.
[144]
Z f Is C 1 ~ C 6 The oxime compound or a salt thereof according to [141], which represents alkoxy.
[145]
A is a hydrogen atom, C 1 ~ C 6 Alkyl or —C (O) R 2 Represents
R 2 Is C 1 ~ C 6 Alkyl or (Z f ) qf Represents phenyl substituted with
R 6 Is C 1 ~ C 6 Represents alkyl,
R 7 Is C 1 ~ C 6 Represents alkyl,
Z 7 Is -S (O) r R 41 Represents
Z 4 Is C 1 ~ C 6 Represents alkoxy,
R 41 Represents D3-60b,
Z 6 And Z 8 Represents a hydrogen atom,
X 3 Represents a halogen atom,
Z f Represents a halogen atom,
qf represents an integer of 1 or 2,
t5 represents the integer of 1; the oxime compound or a salt thereof according to [73].
[146]
Formula (3):
Figure JPOXMLDOC01-appb-C000012
 [Where Q is NOR 7 Represents
A is C 1 ~ C 6 Represents alkyl,
R 6 Is C 1 ~ C 6 Alkyl or C 3 ~ C 8 Represents cycloalkyl,
R 7 Is C 1 ~ C 6 Represents alkyl,
R 8a , R 8b , R 9a And R 9b Represents a hydrogen atom,
Z 4 Is a halogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 Represents alkoxy,
Z 5 Represents a hydrogen atom,
Z 6 And Z 8 Each independently represents a hydrogen atom or C 1 ~ C 6 Represents alkyl,
X 3a Is C 1 ~ C 6 Represents alkyl,
m represents an integer of 1;
n represents an integer of 0;
t4 represents an integer of 4.] The intermediate for producing a compound according to any one of [1] to [145].
[147]
An agrochemical containing one or more selected from the ketone and oxime compounds according to any one of [1] to [145] and salts thereof as an active ingredient.
[148]
A herbicide containing, as an active ingredient, one or more selected from the ketone and oxime compounds according to any one of [1] to [145] and salts thereof.
　本発明化合物は、各種雑草に対して優れた除草活性並びに対象となる作物に対する高い安全性を有し、且つ、ホ乳動物、魚類及び益虫等の非標的生物に対してほとんど悪影響が無く、低残留性で環境に対する負荷も軽い。
　従って、本発明は水田、畑地及び果樹園等の農園芸分野において有用な除草剤を提供することができる。 The compound of the present invention has excellent herbicidal activity against various weeds and high safety against target crops, and has almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects, and has low Persistence and light environmental impact.
Therefore, the present invention can provide a herbicide useful in the field of agriculture and horticulture such as paddy fields, upland fields, and orchards.
　式（１）で表される本発明化合物に関しては、置換基の種類や条件に応じて、場合によっては次式で表されるケト－エノール構造互変異性体の存在が考えられる。故に、置換基Ａを導入した時、エノール構造Ｂ－３からはＢ－１が、Ｂ－４からはＢ－２がそれぞれ製造され、本発明はそれら全ての構造を包含するものである。
Figure JPOXMLDOC01-appb-C000013
 Regarding the compound of the present invention represented by the formula (1), the presence of a keto-enol structure tautomer represented by the following formula may be considered depending on the type and conditions of the substituent. Therefore, when the substituent A is introduced, B-1 is produced from the enol structure B-3, and B-2 is produced from the B-4, and the present invention includes all these structures.
Figure JPOXMLDOC01-appb-C000013
　本発明に包含される化合物には、置換基の種類によってはＥ－体及びＺ－体の幾何異性体が存在する場合がある。本発明はこれらＥ－体、Ｚ－体又はＥ－体及びＺ－体を任意の割合で含む混合物を包含するものであり、本明細書においては、これらを例えば下記のように波線の結合として表す。
Figure JPOXMLDOC01-appb-C000014
 In the compounds included in the present invention, geometric isomers of E-form and Z-form may exist depending on the type of substituent. The present invention encompasses these E-form, Z-form, or a mixture containing E-form and Z-form in any ratio. To express.
Figure JPOXMLDOC01-appb-C000014
　また、本発明に包含される化合物は、１個又は２個以上の不斉炭素原子の存在に起因する光学活性体が存在するが、本発明は全ての光学活性体又はラセミ体を包含する。 In addition, the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.
　本明細書において、以下の用語又は表現は、それぞれ、以下の意味又は用法で使用される。
　本明細書におけるハロゲン原子としては、フッ素原子、塩素原子、臭素原子及び沃素原子が挙げられる。尚、本明細書中「ハロ」の表記もこれらのハロゲン原子を表す。
　各置換基の具体例において、「ｎ－」は「ノルマル」を、「ｉ－」は「イソ」を、「ｓec－」又は「ｓ－」は「セカンダリー」を及び「ｔｅｒｔ－」又は「ｔ－」は「ターシャリー」を各々意味し、Ｐｈはフェニルを意味する。 In this specification, the following terms or expressions are respectively used in the following meanings or usages.
Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. In the present specification, the notation “halo” also represents these halogen atoms.
In specific examples of each substituent, “n-” is “normal”, “i-” is “iso”, “sec-” or “s-” is “secondary” and “tert-” or “t “-” Means “tertiary” and Ph means phenyl.
　本明細書におけるＣａ～Ｃｂアルキルの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の炭化水素基を表し、例えばメチル、エチル、ｎ－プロピル、ｉ－プロピル、ｎ－ブチル、ｉ－ブチル、ｓｅｃ－ブチル、ｔｅｒｔ－ブチル、ペンチル、１，１－ジメチルプロピル、ヘキシル、オクチル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkyl represents a linear or branched hydrocarbon group having a carbon number of a to b, such as methyl, ethyl, n-propyl, i-propyl. , N-butyl, i-butyl, sec-butyl, tert-butyl, pentyl, 1,1-dimethylpropyl, hexyl, octyl, and the like are listed as specific examples, each selected within the range of the designated number of carbon atoms. .
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルキルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の炭化水素基を表し、このとき、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えばフルオロメチル、クロロメチル、ブロモメチル、ヨードメチル、ジフルオロメチル、ジクロロメチル、トリフルオロメチル、クロロジフルオロメチル、トリクロロメチル、ブロモジフルオロメチル、２－フルオロエチル、２－クロロエチル、２－ブロモエチル、２，２－ジフルオロエチル、２，２，２－トリフルオロエチル、２－クロロ－２，２－ジフルオロエチル、２，２，２－トリクロロエチル、１，１，２，２－テトラフルオロエチル、２－クロロ－１，１，２－トリフルオロエチル、ペンタフルオロエチル、３，３，３－トリフルオロプロピル、２，２，３，３，３－ペンタフルオロプロピル、１，１，２，３，３，３－ヘキサフルオロプロピル、ヘプタフルオロプロピル、２，２，２－トリフルオロ－１－（トリフルオロメチル）エチル、１，２，２，２－テトラフルオロ－１－（トリフルオロメチル）エチル、２，２，３，３，４，４，４－ヘプタフルオロブチル、ノナフルオロブチル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, the notation of halo (C a -C b ) alkyl is linear or branched having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom A chain-like hydrocarbon group is represented, and when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoro Ethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1, 1,2-trifluoroethyl, pentafluoroethyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoro Propyl, heptafluoropropyl, 2,2,2-trifluoro-1- (trifluorome Specific examples include ethyl), 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl, 2,2,3,3,4,4,4-heptafluorobutyl and nonafluorobutyl. Each of which is selected for each specified number of carbon atoms.
　本明細書におけるフェニル（Ｃａ～Ｃｂ）アルキルの表記は、炭素原子に結合した水素原子が、フェニルによって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の前記の意味である炭化水素基を表し、例えばベンジル、１－フェネチル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂアルケニルの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の二重結合を有する不飽和炭化水素基を表し、例えばビニル、１－プロペニル、２－プロペニル、１－メチルエテニル、２－ブテニル、２－メチル－２－プロペニル、３－メチル－２－ブテニル、１，１－ジメチル－２－プロペニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, phenyl (C a -C b ) alkyl is represented by a linear or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with phenyl. The hydrocarbon groups having the above-mentioned meanings are exemplified, and for example, benzyl, 1-phenethyl and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
In the present specification, C a -C b alkenyl is a linear or branched chain composed of a to b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group such as vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, 1,1-dimethyl-2- Specific examples include propenyl and the like, each selected within the range of the specified number of carbon atoms.
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルケニルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の二重結合を有する不飽和炭化水素基を表す。このとき、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えば２，２－ジクロロビニル、２－フルオロ－２－プロペニル、２－クロロ－２－プロペニル、３－クロロ－２－プロペニル、２－ブロモ－２－プロペニル、３，３－ジフルオロ－２－プロペニル、２，３－ジクロロ－２－プロペニル、３，３－ジクロロ－２－プロペニル、２，３，３－トリフルオロ－２－プロペニル、２，３，３－トリクロロ－２－プロペニル、１－（トリフルオロメチル）エテニル、４，４－ジフルオロ－３－ブテニル、３，４，４－トリフルオロ－３－ブテニル、３－クロロ－４，４，４－トリフルオロ－２－ブテニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of halo (C a -C b ) alkenyl in this specification refers to a straight or branched chain having a to b carbon atoms, in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom An unsaturated hydrocarbon group which is chain-like and has one or more double bonds in the molecule. At this time, when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, 2,2-dichlorovinyl, 2-fluoro-2-propenyl, 2-chloro-2-propenyl, 3-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 3,3-dichloro-2-propenyl, 2,3,3-trifluoro-2-propenyl, 2,3,3-trichloro-2-propenyl, 1- (trifluoro Specific examples include methyl) ethenyl, 4,4-difluoro-3-butenyl, 3,4,4-trifluoro-3-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, and the like. , Each selected range of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキニルの表記は、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の三重結合を有する不飽和炭化水素基を表し、例えばエチニル、１-プロピニル、２-プロピニル、１-ブチニル、２-ブチニル、３-ブチニル、１，１－ジメチル－２－プロピニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkynyl represents a linear or branched chain having a carbon number of a to b and an unsaturated group having one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1,1-dimethyl-2-propynyl, and the like. Selected in the range of the number of carbon atoms.
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルキニルの表記は、炭素原子に結合した水素原子が、ハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状で、且つ分子内に１個又は２個以上の三重結合を有する不飽和炭化水素基を表す。このとき、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、または互いに相異なっていても良い。例えば２－クロロエチニル、２－ブロモエチニル、２－ヨードエチニル、３－クロロ－２－プロピニル、３－ブロモ－２－プロピニル、３－ヨード－２－プロピニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, the notation of halo (C a -C b ) alkynyl refers to a straight or branched chain having a to b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom An unsaturated hydrocarbon group which is chain-like and has one or more triple bonds in the molecule. At this time, when substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. Specific examples include 2-chloroethynyl, 2-bromoethynyl, 2-iodoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 3-iodo-2-propynyl and the like. In the range of the number of carbon atoms.
　本明細書におけるＣａ～Ｃｂシクロアルキルの表記は、炭素原子数がａ～ｂ個よりなる環状の炭化水素基を表し、３員環から６員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよい。例えばシクロプロピル、１－メチルシクロプロピル、２－メチルシクロプロピル、２，２－ジメチルシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b cycloalkyl represents a cyclic hydrocarbon group having a to b carbon atoms, and forms a monocyclic or complex ring structure having 3 to 6 members. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. For example, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms. .
　本明細書におけるハロ（Ｃａ～Ｃｂ）シクロアルキルの表記は、炭素原子に結合した水素原子がハロゲン原子によって任意に置換された、炭素原子数がａ～ｂ個よりなる環状の炭化水素基を表し、３員環から８員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよく、ハロゲン原子による置換は環構造部分であっても、側鎖部分であっても、或いはそれらの両方であってもよく、さらに、２個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、又は互いに相異なっていてもよい。例えば２,２-ジフルオロシクロプロピル、２,２-ジクロロシクロプロピル、２,２-ジブロモシクロプロピル、２,２-ジフルオロ-１-メチルシクロプロピル、２,２-ジクロロ-１-メチルシクロプロピル、２,２-ジブロモ-１-メチルシクロプロピル、２,２,３,３-テトラフルオロシクロブチル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of halo (C a -C b ) cycloalkyl in the present specification is a cyclic hydrocarbon group having a carbon number of a to b, wherein a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom It is possible to form a monocyclic or complex ring structure from 3 to 8 membered ring. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2, Specific examples include 2,2-dibromo-1-methylcyclopropyl, 2,2,3,3-tetrafluorocyclobutyl, and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂシクロアルケニルの表記は、炭素原子数がａ～ｂ個よりなる環状の、且つ１個又は２個以上の二重結合を有する不飽和炭化水素基を表し、３員環から８員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよく、さらに、二重結合はｅｎｄｏ－又はｅｘｏ－のどちらの形式であってもよい。例えば１－シクロペンテン－１－イル、２－シクロペンテン－１－イル、１－シクロヘキセン－１－イル、２－シクロヘキセン－１－イル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b cycloalkenyl represents a cyclic unsaturated hydrocarbon group having 1 to 2 carbon atoms and having 1 to 2 carbon atoms. A monocyclic or complex ring structure from a member ring to an 8-member ring can be formed. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the double bond may be in an endo- or exo- form. For example, 1-cyclopenten-1-yl, 2-cyclopenten-1-yl, 1-cyclohexen-1-yl, 2-cyclohexen-1-yl and the like can be mentioned as specific examples. Selected.
　本明細書におけるＣａ～Ｃｂアルコキシの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｏ－基を表し、例えばメトキシ、エトキシ、ｎ－プロピルオキシ、ｉ－プロピルオキシ、ｎ－ブチルオキシ、ｉ－ブチルオキシ、ｓｅｃ－ブチルオキシ、ｔｅｒｔ－ブチルオキシ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkoxy represents an alkyl-O— group having the above-mentioned meanings consisting of a to b carbon atoms, such as methoxy, ethoxy, n-propyloxy, i-propyl. Specific examples include oxy, n-butyloxy, i-butyloxy, sec-butyloxy, tert-butyloxy, and the like, each selected within the specified number of carbon atoms.
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルコキシの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｏ－基を表し、例えばジフルオロメトキシ、トリフルオロメトキシ、クロロジフルオロメトキシ、ブロモジフルオロメトキシ、２－フルオロエトキシ、２－クロロエトキシ、２，２，２－トリフルオロエトキシ、１，１，２，２，－テトラフルオロエトキシ、２－クロロ－１，１，２－トリフルオロエトキシ、１，１，２，３，３，３－ヘキサフルオロプロピルオキシ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, the notation of halo (C a -C b ) alkoxy represents a haloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, difluoromethoxy, trifluoromethoxy, chlorodifluoro Methoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2, -tetrafluoroethoxy, 2-chloro-1,1,2-tri Specific examples include fluoroethoxy, 1,1,2,3,3,3-hexafluoropropyloxy, and each is selected in the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂシクロアルキルオキシの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるシクロアルキル－Ｏ－基を表し、例えばシクロプロピルオキシ、２－メチルシクロペンチルオキシ、シクロヘキシルオキシ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるＣａ～Ｃｂアルコキシ（Ｃｃ～Ｃｄ）アルキルの表記は、炭素原子に結合した水素原子が、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の前記の意味であるアルコキシ基によって任意に置換された、炭素原子数がｃ～ｄ個よりなる直鎖状又は分岐鎖状の前記の意味であるアルキル基を表し、このとき、２個以上のアルコキシ基によって置換されている場合、それらのアルコキシ基は互いに同一でも、又は互いに相異なっていてもよい。例えばメトキシメチル、２－エトキシエチル、２，２－ジメトキシエチル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b cycloalkyloxy in the present specification represents a cycloalkyl-O— group having the above-mentioned meaning consisting of a to b carbon atoms, for example, cyclopropyloxy, 2-methylcyclopentyloxy Specific examples include cyclohexyloxy, etc., and each is selected within the range of the designated number of carbon atoms.
In the present specification, C a -C b alkoxy (C c -C d ) alkyl is represented by a straight or branched chain in which a hydrogen atom bonded to a carbon atom has a carbon number of a to b. Represents a linear or branched alkyl group having the above-mentioned meanings having a carbon number of cd, optionally substituted by an alkoxy group having the meaning of When substituted by these, the alkoxy groups may be the same as or different from each other. For example, methoxymethyl, 2-ethoxyethyl, 2,2-dimethoxyethyl and the like can be mentioned as specific examples, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルチオの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｓ－基を表し、例えばメチルチオ、エチルチオ、ｎ－プロピルチオ、ｉ－プロピルチオ、ｎ－ブチルチオ、ｉ－ブチルチオ、ｓｅｃ－ブチルチオ、ｔｅｒｔ－ブチルチオ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, the expression C a -C b alkylthio represents an alkyl-S— group having the above-mentioned meanings comprising a to b carbon atoms, such as methylthio, ethylthio, n-propylthio, i-propylthio, Specific examples include n-butylthio, i-butylthio, sec-butylthio, tert-butylthio and the like, each selected within the range of the designated number of carbon atoms.
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルキルチオの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｓ－基を表し、例えばジフルオロメチルチオ、トリフルオロメチルチオ、クロロジフルオロメチルチオ、ブロモジフルオロメチルチオ、２，２，２－トリフルオロエチルチオ、１，１，２，２－テトラフルオロエチルチオ、２－クロロ－１，１，２－トリフルオロエチルチオ、ペンタフルオロエチルチオ、１，１，２，３，３，３－ヘキサフルオロプロピルチオ、ヘプタフルオロプロピルチオ、１，２，２，２－テトラフルオロ－１－（トリフルオロメチル）エチルチオ、ノナフルオロブチルチオ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of halo (C a -C b ) alkylthio in the present specification represents a haloalkyl-S— group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylthio, trifluoromethylthio, chlorodifluoro Methylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, pentafluoroethylthio, Specific examples include 1,1,2,3,3,3-hexafluoropropylthio, heptafluoropropylthio, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylthio, nonafluorobutylthio and the like Each selected within a range of each specified number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルスルフィニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｓ（Ｏ）－基を表し、例えばメチルスルフィニル、エチルスルフィニル、ｎ－プロピルスルフィニル、ｉ－プロピルスルフィニル、ｎ－ブチルスルフィニル、ｉ－ブチルスルフィニル、ｓｅｃ－ブチルスルフィニル、ｔｅｒｔ－ブチルスルフィニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkylsulfinyl represents an alkyl-S (O) -group having the above-mentioned meanings having a carbon number of a to b, for example, methylsulfinyl, ethylsulfinyl, n- Specific examples include propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl and the like, each selected within the range of the designated number of carbon atoms.
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルキルスルフィニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｓ（Ｏ）－基を表し、例えばジフルオロメチルスルフィニル、トリフルオロメチルスルフィニル、クロロジフルオロメチルスルフィニル、ブロモジフルオロメチルスルフィニル、２，２，２－トリフルオロエチルスルフィニル、１，２，２，２－テトラフルオロ－１－（トリフルオロメチル）エチルスルフィニル、ノナフルオロブチルスルフィニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of halo (C a -C b ) alkylsulfinyl in the present specification represents a haloalkyl-S (O) -group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylsulfinyl, tri Fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethylsulfinyl, nonafluorobutylsulfinyl Etc. are given as specific examples, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルスルホニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－ＳＯ２－基を表し、例えばメチルスルホニル、エチルスルホニル、ｎ－プロピルスルホニル、ｉ－プロピルスルホニル、ｎ－ブチルスルホニル、ｉ－ブチルスルホニル、ｓｅｃ－ブチルスルホニル、ｔｅｒｔ－ブチルスルホニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。
　本明細書におけるハロ（Ｃａ～Ｃｂ）アルキルスルホニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるハロアルキル－Ｓ（Ｏ）２－基を表し、例えばジフルオロメチルスルホニル、トリフルオロメチルスルホニル、クロロジフルオロメチルスルホニル、ブロモジフルオロメチルスルホニル、２，２，２－トリフルオロエチルスルホニル、１，１，２，２－テトラフルオロエチルスルホニル、２－クロロ－１，１，２－トリフルオロエチルスルホニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylsulfonyl in the present specification represents an alkyl-SO 2 -group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl. , I-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.
The notation of halo (C a -C b ) alkylsulfonyl in the present specification represents a haloalkyl-S (O) 2 — group having the above-mentioned meaning consisting of a to b carbon atoms, such as difluoromethylsulfonyl, Trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trimethyl Specific examples include fluoroethylsulfonyl and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルコキシカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｏ－Ｃ（Ｏ）－基を表し、例えばメトキシカルボニル、エトキシカルボニル、ｎ－プロピルオキシカルボニル、ｉ－プロピルオキシカルボニル、ｎ－ブトキシカルボニル、ｉ－ブトキシカルボニル、ｔｅｒｔ－ブトキシカルボニル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkoxycarbonyl represents an alkyl-O—C (O) — group having the above-mentioned meaning of a to b carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, Specific examples include n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, tert-butoxycarbonyl and the like, each selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルカルボニルの表記は、炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル－Ｃ（Ｏ）－基を表し、例えばアセチル、プロピオニル、ブチリル、イソブチリル、バレリル、イソバレリル、２－メチルブタノイル、ピバロイル、ヘキサノイル、ヘプタノイル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylcarbonyl in the present specification represents an alkyl-C (O) — group having the above-mentioned meaning consisting of a to b carbon atoms, such as acetyl, propionyl, butyryl, isobutyryl, Specific examples include valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl and the like, each selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルアミノカルボニルの表記は、水素原子の一方が炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたカルバモイル基を表し、例えばメチルカルバモイル、エチルカルバモイル、ｎ－プロピルカルバモイル、ｉ－プロピルカルバモイル、ｎ－ブチルカルバモイル、ｉ－ブチルカルバモイル、ｓｅｃ－ブチルカルバモイル、ｔｅｒｔ－ブチルカルバモイル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkylaminocarbonyl represents a carbamoyl group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, for example methylcarbamoyl , Ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, sec-butylcarbamoyl, tert-butylcarbamoyl, etc. Selected.
　本明細書におけるジ（Ｃａ～Ｃｂ）アルキルアミノカルボニルの表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたカルバモイル基を表し、例えばＮ，Ｎ－ジメチルカルバモイル、Ｎ－エチル－Ｎ－メチルカルバモイル、Ｎ，Ｎ－ジエチルカルバモイル、Ｎ，Ｎ－ジ（ｎ－プロピル）カルバモイル、Ｎ，Ｎ－ジ（ｎ－ブチル）カルバモイル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, the notation of di (C a -C b ) alkylaminocarbonyl means in the above meaning that the number of carbon atoms which may be the same or different from each other is a to b. Represents a carbamoyl group substituted by an alkyl group, such as N, N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N, N-diethylcarbamoyl, N, N-di (n-propyl) carbamoyl, N, Specific examples include N-di (n-butyl) carbamoyl and the like, and each is selected within the range of the designated number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルアミノの表記は、水素原子の一方が炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたアミノ基を表し、例えばメチルアミノ、エチルアミノ、ｎ－プロピルアミノ、ｉ－プロピルアミノ、ｎ－ブチルアミノ、ｉ－ブチルアミノ、ｔｅｒｔ－ブチルアミノ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 The notation of C a -C b alkylamino in the present specification represents an amino group in which one of the hydrogen atoms is substituted with an alkyl group having the above-mentioned meaning consisting of a to b carbon atoms, such as methylamino, Specific examples include ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, tert-butylamino, etc., each selected within the specified number of carbon atoms.
　本明細書におけるジ（Ｃａ～Ｃｂ）アルキルアミノの表記は、水素原子が両方とも、それぞれ同一でも又は互いに相異なっていてもよい炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基によって置換されたアミノ基を表し、例えばジメチルアミノ、エチル（メチル）アミノ、ジエチルアミノ、ｎ－プロピル（メチル）アミノ、ｉ－プロピル（メチル）アミノ、ジ（ｎ－プロピル）アミノ、ジ（ｎ－ブチル）アミノ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, the notation of di (C a -C b ) alkylamino has the above-mentioned meaning that the number of carbon atoms in which both hydrogen atoms may be the same or different from each other consists of a to b. Represents an amino group substituted by an alkyl group, such as dimethylamino, ethyl (methyl) amino, diethylamino, n-propyl (methyl) amino, i-propyl (methyl) amino, di (n-propyl) amino, di (n Specific examples include -butyl) amino and the like, each selected within the range of the specified number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルキルカルボニルアミノの表記は、水素原子の一方が炭素原子数がａ～ｂ個よりなる前記の意味であるアルキルカルボニル基によって置換されたアミノ基を表し、例えばアセチルアミノ、プロピオニルアミノ、イソブチリルアミノ、ピバロイルアミノ等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkylcarbonylamino represents an amino group in which one of the hydrogen atoms is substituted with an alkylcarbonyl group having the above-mentioned meaning consisting of a to b carbon atoms. Specific examples include amino, propionylamino, isobutyrylamino, pivaloylamino, and the like, each selected within the specified number of carbon atoms.
　本明細書におけるＣａ～Ｃｂアルコキシカルボニル（Ｃｃ～Ｃｄ）アルキルの表記は、炭素原子に結合した水素原子が、炭素原子数がａ～ｂ個よりなる直鎖状又は分岐鎖状の前記の意味であるアルコキシカルボニル基によって任意に置換された、炭素原子数がｃ～ｄ個よりなる直鎖状又は分岐鎖状の前記の意味であるアルキル基を表し、例えばメトキシカルボニルメチル、エトキシカルボニルエチル、エトキシカルボニルプロピル、ペンチルオキシカルボニルブチル、エチルへキシルオキシカルボニルエチル、ブトキシカルボニルエチル等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。 In the present specification, C a -C b alkoxycarbonyl (C c -C d ) alkyl is a straight or branched chain in which a hydrogen atom bonded to a carbon atom has a carbon number of a to b. Represents a linear or branched alkyl group having the above-mentioned meanings having a carbon number of cd, optionally substituted by an alkoxycarbonyl group as defined above, for example, methoxycarbonylmethyl, ethoxycarbonyl Specific examples include ethyl, ethoxycarbonylpropyl, pentyloxycarbonylbutyl, ethylhexyloxycarbonylethyl, butoxycarbonylethyl, etc., each selected within the specified number of carbon atoms.
　本明細書における「Ｒ５で任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ５ａで任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ５ｂで任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ５ｆで任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ５ｇで任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ6ｂで任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ７ｂで任意に置換された（Ｃａ～Ｃｂ）アルキル」、「Ｒ２０にで任意に置換された（Ｃａ～Ｃｂ）アルキル」及び「Ｒ２０ｆで任意に置換された（Ｃａ～Ｃｂ）アルキル」等の表記は、炭素原子に結合した水素原子がそれぞれの置換基Ｒ５等によって置換された炭素原子数がａ～ｂ個よりなる前記の意味であるアルキル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの置換基が２個以上存在するとき、それぞれの置換基は互いに同一でも異なってもよい。 "Optionally substituted with R 5 (C a ~ C b ) alkyl" as used herein, "optionally substituted with R 5a (C a ~ C b ) alkyl" optionally substituted with "R 5b and (C a ~ C b) alkyl "," optionally substituted with R 5f (C a ~ C b ) alkyl "," optionally substituted with R 5g (C a ~ C b ) alkyl "," optionally substituted with R 6b (C a ~ C b ) alkyl "," optionally substituted with R 7b (C a ~ C b ) alkyl "," optionally substituted with R 20 two (C a ~ C b) alkyl ", and" transcription of optionally substituted (C a ~ C b) alkyl ", etc. in R 20f, the carbon hydrogen atoms bonded to carbon atoms are replaced by each of the substituents R 5, etc. Represents an alkyl group having the above-mentioned meaning of a to b atoms, Of being selected in the range of number of carbon atoms. At this time, when two or more of each substituent exists, each substituent may be the same as or different from each other.
　本明細書における「Ｒ５で任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ５ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ５ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ５ｆで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ５ｇで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ６ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ７ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」、「Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」及び「Ｒ２０ｆで任意に置換された（Ｃａ～Ｃｂ）シクロアルキル」の表記は、炭素原子に結合した水素原子がそれぞれの置換基Ｒ５等によって置換された炭素原子数がａ～ｂ個よりなる前記の意味であるシクロアルキル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの置換基が２個以上存在するとき、それぞれの置換基は互いに同一でも異なってもよく、さらに置換位置は環構造部分であっても、側鎖部分であっても、或いはそれらの両方にあってもよい。 "Optionally substituted with R 5 (C a ~ C b ) cycloalkyl" as used herein, "optionally substituted with R 5a (C a ~ C b ) cycloalkyl", optionally in the "R 5b substituted (C a ~ C b) cycloalkyl "," optionally substituted with R 5f (C a ~ C b ) cycloalkyl "," optionally substituted with R 5g (C a ~ C b ) cycloalkyl "," optionally substituted with R 6b (C a ~ C b ) cycloalkyl "," optionally substituted with R 7b (C a ~ C b ) cycloalkyl ", optionally in the" R 20 substituted (C a ~ C b) cycloalkyl "and" notation optionally substituted with R 20f (C a ~ C b ) cycloalkyl ", each substituent is a hydrogen atom bonded to a carbon atom R A to b carbon atoms substituted by 5 etc. Each of which is selected within the range of the designated number of carbon atoms. In this case, when there are two or more substituents, the substituents may be the same or different from each other, and the substitution position may be a ring structure part, a side chain part, or May be in both.
　本明細書における「Ｒ５で任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ５ａで任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ５ｂで任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ５ｆで任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ５ｇで任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ６ｂで任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ７ｂで任意に置換された（Ｃａ～Ｃｂ）アルケニル」、「Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）アルケニル」及び「Ｒ２０ｆで任意に置換された（Ｃａ～Ｃｂ）アルケニル」の表記は、炭素原子に結合した水素原子がそれぞれの置換基Ｒ５等によって置換された炭素原子数がａ～ｂ個よりなる前記の意味であるアルケニル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの置換基が２個以上存在するとき、それぞれの置換基は互いに同一でも異なってもよい。 "Optionally substituted with R 5 (C a ~ C b ) alkenyl" in the present specification, "optionally substituted with R 5a (C a ~ C b ) alkenyl", optionally substituted with "R 5b and (C a ~ C b) alkenyl "," optionally substituted with R 5f (C a ~ C b ) alkenyl "," optionally substituted with R 5g (C a ~ C b ) alkenyl "," (C a -C b ) alkenyl optionally substituted with R 6b , “(C a -C b ) alkenyl optionally substituted with R 7b ”, “(C a -C b ) alkenyl optionally substituted with R 20 (C a- The notation of “C b ) alkenyl” and “(C a -C b ) alkenyl optionally substituted with R 20f ” refers to the number of carbon atoms in which the hydrogen atom bonded to the carbon atom is substituted by the respective substituent R 5 or the like. Is an alkenyl group as defined above consisting of a to b Each selected within a range of each specified number of carbon atoms. At this time, when two or more of each substituent exists, each substituent may be the same as or different from each other.
　本明細書における「Ｒ５で任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ５ａで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ５ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ５ｆで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ５ｇで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ６ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ７ｂで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」、「Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」及び「Ｒ２０ｆで任意に置換された（Ｃａ～Ｃｂ）シクロアルケニル」の表記は、炭素原子に結合した水素原子がそれぞれの置換基Ｒ５等によって置換された炭素原子数がａ～ｂ個よりなる前記の意味であるシクロアルケニル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの置換基が２個以上存在するとき、それぞれの置換基は互いに同一でも異なってもよく、さらに置換位置は環構造部分であっても、側鎖部分であっても、或いはそれらの両方にあってもよい。 "Optionally substituted with R 5 (C a ~ C b ) cycloalkenyl" herein, "optionally substituted with R 5a (C a ~ C b ) cycloalkenyl", optionally in the "R 5b substituted (C a ~ C b) cycloalkenyl "," optionally substituted with R 5f (C a ~ C b ) cycloalkenyl "," optionally substituted with R 5g (C a ~ C b ) cycloalkenyl "," optionally substituted with R 6b (C a ~ C b ) cycloalkenyl "," optionally substituted with R 7b (C a ~ C b ) cycloalkenyl ", optionally in the" R 20 substituted (C a ~ C b) cycloalkenyl "and" notation optionally substituted with R 20f (C a ~ C b ) cycloalkenyl ", each substituent is a hydrogen atom bonded to a carbon atom R Charcoal replaced by 5 etc. It represents a cycloalkenyl group having the above-mentioned meaning consisting of a to b number of elementary atoms, and is selected in the range of each designated number of carbon atoms. In this case, when there are two or more substituents, the substituents may be the same or different from each other, and the substitution position may be a ring structure part, a side chain part, or May be in both.
　本明細書における「Ｒ５で任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ５ａで任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ５ｂで任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ５ｆで任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ５ｇで任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ６ｂで任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ７ｂで任意に置換された（Ｃａ～Ｃｂ）アルキニル」、「Ｒ２０で任意に置換された（Ｃａ～Ｃｂ）アルキニル」及び「Ｒ２０ｆで任意に置換された（Ｃａ～Ｃｂ）アルキニル」の表記は、炭素原子に結合した水素原子がそれぞれの置換基Ｒ５等によって置換された炭素原子数がａ～ｂ個よりなる前記の意味であるアルキニル基を表し、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの置換基が２個以上存在するとき、それぞれの置換基は互いに同一でも異なってもよい。
　本明細書における農薬とは、農園芸分野における殺虫・殺ダニ剤、殺線虫剤、除草剤及び殺菌剤等を意味する。 "Optionally substituted with R 5 (C a ~ C b ) alkynyl" herein, "optionally substituted with R 5a (C a ~ C b ) alkynyl", optionally substituted with "R 5b and (C a ~ C b) alkynyl "," optionally substituted with R 5f (C a ~ C b ) alkynyl "," optionally substituted with R 5g (C a ~ C b ) alkynyl, "" optionally substituted with R 6b (C a ~ C b ) alkynyl "," optionally substituted with R 7b (C a ~ C b ) alkynyl "," optionally substituted with R 20 (C a ~ The notation of “C b ) alkynyl” and “(C a -C b ) alkynyl optionally substituted with R 20f ” is the number of carbon atoms in which the hydrogen atom bonded to the carbon atom is substituted by the respective substituent R 5 An alkynyl group as defined above comprising a to b Each selected within a range of each specified number of carbon atoms. At this time, when two or more of each substituent exists, each substituent may be the same as or different from each other.
An agrochemical in this specification means an insecticide / acaricide, a nematicide, a herbicide, a fungicide, etc. in the field of agriculture and horticulture.
　本明細書における除草剤とは、水田、畑地及び果樹園等において、作物の生育に悪影響を与える雑草、公園等の芝地において、芝の生育に悪影響を与える雑草、運動場、空地、駐車場、道路脇及び線路端等の非農耕地に無秩序に繁茂する雑草を防除するための薬剤を意味する。 In this specification, the herbicides are weeds that adversely affect the growth of crops in paddy fields, upland fields, orchards, etc. It means chemicals for controlling weeds that grow randomly on non-agricultural land such as roadsides and track ends.
　本明細書における雑草とは、水田、畑地、果樹園等の農耕地及び芝地、運動場、空地、駐車場、道路脇、線路端等の非農耕地に自然発生する植物を意味する。
　水田に発生する雑草としては、例えば、ヒルムシロ（Potamogeton distinctus）等に代表されるヒルムシロ科（Potamogetonaceae）雑草、ヘラオモダカ（Alisma canaliculatum）、ウリカワ（Sagittaria pygmaea）及びオモダカ（Sagittaria trifolia）等に代表されるオモダカ科（Alismataceae）雑草、アゼガヤ（Leptochloa chinensis）、イヌビエ（Echinochloa crus-galli）、タイヌビエ（Echinochloa oryzicola）、アシカキ（Homalocenchrus japonocus）及びキシュウスズメノヒエ（Paspalum distichum）等に代表されるイネ科（Gramineae）雑草、クログワイ（Eleocharis kuroguwai）、ホタルイ（Scirpus juncoides）、シズイ（Scirpus nipponicus）、ミズガヤツリ（Cyperus serotinus）、タマガヤツリ（Cyperus difformis）及びヒナガヤツリ（Cyperus hakonensis）等に代表されるカヤツリグサ科（Cyperaceae）雑草、ウキクサ（Spirodela polyrhiza）及びアオウキクサ（Lemna paucicostata）等に代表されるウキクサ科（Lemnaceae）雑草、イボクサ（Murdannia keisak）等に代表されるツユクサ科（Commelinaceae）雑草、ミズアオイ（Monochoria korsakowii）及びコナギ（Monochoria vaginalis）等に代表されるミズアオイ科（Pontederiaceae）雑草、ミゾハコベ（Elatine triandra）等に代表されるミゾハコベ科（Elatinaceae）雑草、ヒメミソハギ（Ammannia multiflora）及びキカシグサ（Rotala indica）等に代表されるミソハギ科（Lythraceae）雑草、チョウジタデ（Lidwigia epilobioides）等に代表されるアカバナ科（Oenotheraceae）雑草、アブノメ（Dopatrium junceum）、オオアブノメ（Gratiola japonica）、キクモ（Limnophila sessilifolia）、アゼナ（Lindernia pyxidaria）及びアメリカアゼナ（Lindernia dubia）等に代表されるゴマノハグサ科（Scrophulariaceae）雑草、クサネム（Aeschynomene indica）等に代表されるマメ科（Leguminosae）雑草、並びにアメリカセンダングサ（Bidens frondosa）及びタウコギ（Bidens tripartita）等に代表されるキク科（Compositae）雑草等が挙げられる。
　畑地及び果樹園に発生する雑草としては、例えば、イヌホウズキ（Solanum nigrum）及びチョウセンアサガオ（Datura stramonium）等に代表されるナス科（Solanaceae）雑草、アメリカフウロ(Granium carolinianum)等に代表されるフウロソウ科（Geraniaceae）雑草、イチビ（Abutilon theophrasti）及びアメリカキンゴジカ（Sida spinosa）等に代表されるアオイ科（Malvaceae）雑草、マルバアサガオ（Ipomoea purpurea）等のアサガオ類（Ipomoea spps．）及びヒルガオ類（Calystegia spps．）等に代表されるヒルガオ科（Convolvulaceae）雑草、イヌビユ（Amaranthus lividus）及びアオビユ（Amaranthus retroflexus）等に代表されるヒユ科（Amaranthaceae）雑草、オナモミ（xanthium pensylvanicum）、ブタクサ（Ambrosia artemisiaefolia）、ヒマワリ（Helianthus annuus）、ハキダメギク（Galinsoga ciliata）、セイヨウトゲアザミ（Cirsium arvense）、ノボロギク（Senecio vulgaris）及びヒメジョン（Erigeron annus）等に代表されるキク科（Compositae）雑草、イヌガラシ（Rorippa indica）、ノハラガラシ（Sinapis arvensis）及びナズナ（Capsella Bursapastoris）等に代表されるアブラナ科（Cruciferae）雑草、イヌタデ（Polygonum Blumei）及びソバカズラ（Polygonum convolvulus）等に代表されるタデ科（Polygonaceae）雑草、スベリヒユ（Portulaca oleracea）等に代表されるスベリヒユ科（Portulacaceae）雑草、シロザ（Chenopodium album）、コアカザ（Chenopodium ficifolium）及びホウキギ（Kochia scoparia）等に代表されるアカザ科（Chenopodiaceae）雑草、ハコベ（Stellaria media）等に代表されるナデシコ科（Caryophyllaceae）雑草、オオイヌノフグリ（Veronica persica）等に代表されるゴマノハグサ科（Scrophulariaceae）雑草、ツユクサ（Commelina communis）等に代表されるツユクサ科（Commelinaceae）雑草、ホトケノザ（Lamium amplexicaule）及びヒメオドリコソウ（Lamium purpureum）等に代表されるシソ科（Labiatae）雑草、コニシキソウ（Euphorbia supina）及びオオニシキソウ（Euphorbia maculata）等に代表されるトウダイグサ科（Euphorbiaceae）雑草、ヤエムグラ（Galium spurium）及びアカネ（Rubia akane）等に代表されるアカネ科（Rubiaceae）雑草、スミレ（Viola mandshurica）等に代表されるスミレ科（Violaceae）雑草並びにアメリカツノクサネム（Sesbania exaltata）及びエビスグサ（Cassia obtusifolia）等に代表されるマメ科（Leguminosae）雑草、カタバミ（Oxsalis courniculata）に代表されるカタバミ科（Oxsaldaseae）等の広葉雑草（Broad-leaved weeds）。野生ソルガム（Sorgham bicolor）、オオクサキビ（Panicum dichotomiflorum）、ジョンソングラス（Sorghum halepense）、イヌビエ（Echinochloa crus-galli var． crus-galli）、ヒメイヌビエ（Echinochloa crus-galli var． praticola）、栽培ビエ（Echinochloa utilis）、メヒシバ（Digitaria ciliaris）、カラスムギ（Avena fatua）、ブラックグラス（Alopecurus myosuroides）、オヒシバ（Eleusine indica）、エノコログサ（Setaria viridis）、アキノエノコログサ（Setaria faberi）及びスズメノテッポウ（Alopecurus aegualis）等に代表されるイネ科雑草（Graminaceous weeds）並びにハマスゲ（Cyperus rotundus，Cyperus esculentus）等に代表されるカヤツリグサ科雑草（Cyperaceous weeds）等が挙げられる。
　非農耕地に発生する雑草としては、畑地及び果樹園の雑草で述べたものに加えて、例えば、スズメノカタビラ（Poa annua）、セイヨウタンポポ（Taraxacum officinale）、オオアレチノギク（Conyza sumatrensis）、タネツケバナ（Cardamine flexuosa）、シロツメクサ（Trifolium repens）、チドメグサ（Hydrocotyle sibthorpioides）、オオバコ（Plantago asiatica）、ヒメクグ（Cyperus brevifolius、Kyllinga brevifolia）、スギナ（Equisetum arvense）等が挙げられる。 The weed in this specification means a plant that naturally occurs in non-agricultural lands such as paddy fields, upland fields, orchards, and turf fields, playgrounds, open spaces, parking lots, roadsides, track ends, and the like.
As the weeds that occur in paddy fields, for example, weeping pods (Potamogetonaceae) represented by potato moget (Potamogeton distinctus), etc. Weeds, Alismataceae weeds, Leptochloa chinensis, Echinochloa crus-galli, Echinochloa oryzicola, Hashilocenchrus japonocus and Paspalum distichum Periaceae, such as crocodile (Eleocharis kuroguwai), firefly (Scirpus juncoides), shirui (Scirpus nipponicus), cyperus serotinus, cyperus difformis, pi (Cyperus hakonensis) polyrhiza) and Lemnaceae weed represented by Lemna paucicostata, etc., Commelinaceae weed represented by Murdannia keisak, Monochoria korsakowii and Monochoria vaginalis, etc. Weeds represented by Pontederiaceae weeds, Elatinaceae weeds such as Elatine triandra, Ammannia multiflora and Lythraceia weeds represented by Rotala indica Oenotheraceae weed represented by epilobioides etc., Abomame (Dopatrium junceum), Giant Abnome (Gratiola japonica), Chrysanthemum (Limnophila sessilifolia), Azena (Lindernia pyxidaria), Sesameaceae represented by American Linda (Lindernia dubia), etc. (Scrophulariaceae) Weed, Kusanem Aeschynomene indica) leguminous typified etc. (Leguminosae) weeds, and Bidens frondosa (Bidens frondosa) and Bidens Tripartita (Asteraceae represented by Bidens tripartita), etc. (Compositae) weeds and the like.
Examples of weeds occurring in upland fields and orchards include, for example, solanaceae weeds represented by Solanum nigrum and Datura stramonium, and sourdaceae represented by American floras (Geraniaceae) weeds, Abutilon theophrasti and blue-tailed deer (Malvaceae) weeds represented by Sida spinosa, etc., Ipomoea purpurea and other morning glory (Ipomoea spps.) And convolvulus Spps. Sunflower (Helianthus annuus), yellowfin (Glinsoga ciliata), Atlantic horsetail (Cirsium arvense), representatives such as Senecio vulgaris, Erigeron annus, and so on, Compositae weeds, Rorippa indica, Sinapis arvensis, and Capsella Bursapastoris Cruciferae weeds, Polygonum Blumei, Polygonum convolvulus, and other Polygonaceae weeds, Portulaca oleracea, and others album), Kano (Chenopodium ficifolium), Kochia scoparia, and other representatives of the mosquito (Chenopodiaceae) weed, Stellaria media, (Caryophyllaceae), Weed, Veronica persica, etc. A typical croaker family (Scrophulariaceae) weed, Commelina communis) such as Commelinaceae weed, Lamium amplexicaule and Lamium purpureum, Labiatae weed, Euphorbia supina and Euphorbia maculata Euphorbia macul Euphorbiaceae weeds represented by, Euglebi (Galium spurium), Rubiaceae weeds represented by Rubia akane, Violaceae weeds represented by Viola mandshurica, etc. And broad-leaved weeds such as legumes (Leguminosae) represented by Sesbania exaltata and Cassia obtusifolia, and broad-leaved weeds represented by Oxsalis courniculata (Oxsaldaseae) . Wild sorghum (Sorgham bicolor), green squirrel (Panicum dichotomiflorum), Johnson grass (Sorghum halepense), Invier (Echinochloa crus-galli var. Crus-galli), Echinochloa crus-galli var. Praticola, ochae ach , Citrus (Digitaria ciliaris), Oats (Avena fatua), Blackgrass (Alopecurus myosuroides), Crimson (Eleusine indica), Enocorogusa (Setaria viridis), Aquinoenogurossa (Setaria faberi) and Suzumenoteppo (Alopecurus aeg) Examples include weeds (Graminaceous weeds) and cyperaceous weeds (Cyperus rotundus, Cyperus esculentus).
As weeds occurring in non-agricultural land, in addition to those mentioned in the field and orchard weeds, for example, Poa annua, Taraxacum officinale, Conyza sumatrensis, Cardamine flexuosa, Examples include Trifolium repens, Hydrocotyle sibthorpioides, Planago asiatica, Cyperus brevifolius, Kyllinga brevifolia, and Equisetum arvense.
　本明細書における作物とは、畑作物或いは水田作物、園芸作物、芝、果樹などを包含し、具体的には例えば、トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピーナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ及びタバコ等の農作物類；ナス科野菜（ナス、トマト、ピーマン、トウガラシ、ジャガイモ等）、ウリ科野菜（キュウリ、カボチャ、ズッキーニ、スイカ、メロン等）、アブラナ科野菜（ダイコン、カブ、セイヨウワサビ、コールラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等）、キク科野菜（ゴボウ、シュンギク、アーティチョーク、レタス等）、ユリ科野菜（ネギ、タマネギ、ニンニク、アスパラガス）、セリ科野菜（ニンジン、パセリ、セロリ、アメリカボウフウ等）、アカザ科野菜（ホウレンソウ、フダンソウ等）、シソ科野菜（シソ、ミント、バジル等）、イチゴ、サツマイモ、ヤマノイモ及びサトイモ等の野菜類；仁果類（リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等）、核果類（モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等）、カンキツ類（ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等）、堅果類（クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等）、液果類（ブルーベリー、クランベリー、ブラックベリー、ラズベリー等）、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ及びアブラヤシ等の果実類；チャ、クワ、街路樹（トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ、ニレ、トチノキ等）、サンゴジュ、イヌマキ、スギ、ヒノキ、クロトン、マサキ及びカナメモチ等の果樹以外の樹木類；シバ類（ノシバ、コウライシバ等）、バミューダグラス類（ギョウギシバ等）、ベントグラス類（コヌカグサ、ハイコヌカグサ、イトコヌカグサ等）、ブルーグラス類（ナガハグサ、オオスズメノカタビラ等）、フェスク類（オニウシノケグサ、イトウシノケグサ、ハイウシノケグサ等）、ライグラス類（ネズミムギ、ホソムギ等）、カモガヤ及びオオアワガエリ等の芝生類；オイルパーム及びナンヨウアブラギリ等の油糧作物類；花卉類（バラ、カーネーション、キク、トルコギキョウ、カスミソウ、ガーベラ、マリーゴールド、サルビア、ペチュニア、バーベナ、チューリップ、アスター、リンドウ、ユリ、パンジー、シクラメン、ラン、スズラン、ラベンダー、ストック、ハボタン、プリムラ、ポインセチア、グラジオラス、カトレア、デージー、バーベナ、シンビジューム、ベゴニア等）；観葉植物等を挙げることができるがこれらに限定されるものではない。
　更に、上記作物には、イソキサフルトール等のHPPD阻害剤、イマゼタピル、チフェンスルフロンメチル等のALS阻害剤、グリホサート等のEPSP合成酵素阻害剤、グルホシネート等のグルタミン合成酵素阻害剤、セトキシジム等のアセチルCoAカルボキシラーゼ阻害剤、フルミオキサジン等のPPO阻害剤、ブロモキシニル、ジカンバ及び2,4-D等の除草剤に対する耐性を古典的な育種法、ならびに遺伝子組換え技術により付与された農園芸用植物も含まれる。 The crops in this specification include field crops, paddy field crops, horticultural crops, turf, fruit trees, etc., specifically, for example, corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut. Crops such as buckwheat, sugar beet, rapeseed, sunflower, sugarcane and tobacco; solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbitae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), oilseed rape Vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (green onion, onion, garlic, asparagus) ), Celery vegetables (carrot, parsley, celery, a Ribbon Fufu, etc.), Rubiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (shiso, mint, basil, etc.), vegetables such as strawberries, sweet potatoes, yam and taro; berries (apples, pears, Japanese pears, karin) , Quince, etc.), nuts (peach, plum, nectarine, ume, sweet cherry, apricot, prunes, etc.), citrus (such as citrus, orange, lemon, lime, grapefruit), nuts (chestnut, walnut, hazel, almond, Pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, oysters, olives, loquat, bananas, coffee, dates, coconut palms, oil palms, etc .; Roadside trees (ash, birch, Dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, red-footed bean, fu, plane tree, zelkova, black beetle, Japanese amberjack, spider, mouse, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, Trees other than fruit trees such as croton, masaki and kanamochi; Shiba (Noshiba, Kourashiba, etc.), Bermudagrass (Gyogishiba, etc.), Bentgrass (Konukagusa, Hykonukagusa, Itokonukagusa, etc.), Bluegrass (Nagahagusa, Giant) Sparrows, etc.), fescues (such as Eurythus japonicus, duckweeds, etc.), ryegrass (such as mud wheat and barley), lawns such as hemlock and prickly crabs; oil crops such as oil palm and oilseed moth; , Mosquito Nation, chrysanthemum, eustoma, gypsophila, gerbera, marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ha button, primula, poinsettia, gladiolus, cattleya, daisy , Verbena, cymbidium, begonia, etc.); foliage plants and the like can be mentioned, but the invention is not limited to these.
Furthermore, the above-mentioned crops include HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Agricultural and horticultural plants that have been given resistance to acetyl-CoA carboxylase inhibitors, PPO inhibitors such as flumioxazin, herbicides such as bromoxynil, dicamba and 2,4-D by classical breeding methods and genetic engineering techniques included.
　古典的な育種法により耐性を付与された農園芸用植物の例として、イマゼタピル等のイミダゾリノン系ALS阻害型除草剤に耐性のナタネ、コムギ、ヒマワリ、イネ、トウモロコシがありClearfield（商品名）の商品名で既に販売されている。
　同様に、古典的な育種法によるチフェンスルフロンメチル等のスルホニルウレア系ALS阻害型除草剤に耐性のダイズがあり、STSダイズの商品名で既に販売されている。同様に古典的な育種法によりトリオンオキシム系、アリールオキシフェノキシプロピオン酸系除草剤などのアセチルCoAカルボキシラーゼ阻害剤に耐性が付与された農園芸用植物の例としてSRコーン等がある。アセチルCoAカルボキシラーゼ阻害剤に耐性が付与された農園芸用植物はプロシーディングズ・オブ・ザ・ナショナル・アカデミー・オブ・サイエンシーズ・オブ・ジ・ユナイテッド・ステーツ・オブ・アメリカ（Proc.Natl.Acad.Sci.USA）87巻、7175～7179頁（1990年）等に記載されている。又アセチルCoAカルボキシラーゼ阻害剤に耐性の変異アセチルCoAカルボキシラーゼがウィード・サイエンス（Weed Science）53巻、728～746頁（2005年）等に報告されており、こうした変異アセチルCoAカルボキシラーゼ遺伝子を遺伝子組換え技術により植物に導入するかもしくは抵抗性付与に関わる変異を作物アセチルCoAカルボキシラーゼに導入する事により、アセチルCoAカルボキシラーゼ阻害剤に耐性の植物を作出することができる。更に、キメラプラスティ技術（Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318）に代表される塩基置換変異導入核酸を植物細胞内に導入して作物（アセチルCoAカルボキシラーゼ/除草剤標的）遺伝子に部位特異的アミノ酸置換変異を引き起こすことにより、アセチルCoAカルボキシラーゼ阻害剤/除草剤に耐性の植物を作出することができる。 Examples of agricultural and horticultural plants that have been rendered tolerant by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. Already sold under the brand name.
Similarly, there are soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods and are already sold under the trade name STS soybeans. Similarly, SR corn and the like are examples of agricultural and horticultural plants imparted with resistance to acetyl-CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods. Agro-horticultural plants tolerated by acetyl-CoA carboxylase inhibitors are Procedures of the National Academy of Sciences of the United States of America (Proc.Natl.Acad) Sci. USA) 87, 7175-7179 (1990). Mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science 53, 728-746 (2005). A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation associated with imparting resistance into a plant by introducing a mutation into the plant acetyl-CoA carboxylase. Furthermore, a base substitution mutation-introduced nucleic acid represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into plant cells to produce crops (acetyl CoA carboxylase / herbicide). Plants resistant to acetyl-CoA carboxylase inhibitors / herbicides can be created by inducing site-specific amino acid substitution mutations in the target) gene.
　遺伝子組換え技術により耐性を付与された農園芸用植物の例として、グリホサート耐性のトウモロコシ、ダイズ、ワタ、ナタネ、テンサイ品種があり、ラウンドアップレディ（RoundupReady）（商品名）、アグリシュアー・GT（AgrisureGT）（商品名）等の商品名で既に販売されている。同様に遺伝子組換え技術によるグルホシネート耐性のトウモロコシ、ダイズ、ワタ、ナタネ品種があり、リバティーリンク（LibertyLink）（商品名）等の商品名で既に販売されている。同様に遺伝子組換え技術によるブロモキシニル耐性のワタはBXNの商品名で既に販売されている。 Examples of agricultural and horticultural plants that have been rendered tolerant by genetic engineering techniques include glyphosate-resistant corn, soybean, cotton, rapeseed, sugar beet varieties, RoundupReady (trade name), Aglisher GT ( AgrisureGT) (brand name) and other brand names are already sold. Similarly, there are glufosinate-resistant maize, soybean, cotton, and rapeseed varieties using genetic engineering techniques, which are already sold under trade names such as LibertyLink (trade name). Similarly, bromoxynyl-resistant cotton using genetic recombination technology has already been sold under the brand name BXN.
　上記農園芸用植物には、遺伝子組換え技術を用いて、例えば、バチルス属で知られている選択的毒素等を合成する事が可能となった植物も含まれる。
　この様な遺伝子組換え植物で発現される殺虫性毒素としては、例えばバチルス・セレウス（Bacillus cereus）やバチルス・ポピリエ（Bacillus popilliae）由来の殺虫性タンパク；バチルス・チューリンゲンシス（Bacillus thuringiensis）由来のCry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1又はCry9C等のδ-エンドトキシン、VIP1、VIP2、VIP3又はVIP3A等の殺虫性タンパク；線虫由来の殺虫性タンパク；さそり毒素、クモ毒素、ハチ毒素又は昆虫特異的神経毒素等の動物によって産生される毒素；糸条菌類毒素；植物レクチン；アグルチニン；トリプシン阻害剤、セリンプロテアーゼ阻害剤、パタチン、シスタチン、パパイン阻害剤等のプロテアーゼ阻害剤；リシン、トウモロコシ-RIP、アブリン、サポリン、ブリオジン等のリボゾーム不活性化タンパク（RIP）；3-ヒドロキシステロイドオキシダーゼ、エクジステロイド-UDP-グルコシルトランスフェラーゼ、コレステロールオキシダーゼ等のステロイド代謝酵素；エクダイソン阻害剤；HMG-CoAリダクターゼ；ナトリウムチャネル阻害剤、カルシウムチャネル阻害剤等のイオンチャネル阻害剤；幼若ホルモンエステラーゼ；利尿ホルモン受容体；スチルベンシンターゼ；ビベンジルシンターゼ；キチナーゼ；グルカナーゼ等が挙げられる。
　また、この様な遺伝子組換え植物で発現される毒素として、Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1又はCry9C等のδ-エンドトキシンタンパク、VIP1、VIP2、VIP3又はVIP3A等の殺虫性タンパクのハイブリッド毒素、一部を欠損した毒素、修飾された毒素も含まれる。ハイブリッド毒素は組換え技術を用いて、これらタンパクの異なるドメインの新しい組み合わせによって作り出される。一部を欠損した毒素としては、アミノ酸配列の一部を欠損したCry1Abが知られている。修飾された毒素としては、天然型毒素のアミノ酸の1つ又は複数が置換されている。
　これら毒素の例及びこれら毒素を合成する事ができる組換え植物は、例えばEP-A-0374753、WO93/07278、WO95/34656、EP-A-0427529、EP-A-451878、WO03/052073等の特許文献に記載されている。これらの組換え植物に含まれる毒素は、特に、鞘翅目害虫、双翅目害虫、鱗翅目害虫への耐性を植物へ付与する。 The agricultural and horticultural plants also include plants that can synthesize selective toxins known in the genus Bacillus using genetic recombination techniques.
Examples of insecticidal toxins expressed in such transgenic plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; Cry1Ab derived from Bacillus thuringiensis , Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; scorpion toxin, spider toxin, bee toxin or Toxins produced by animals such as insect-specific neurotoxins; filamentous fungi toxins; plant lectins; agglutinins; trypsin inhibitors, serine protease inhibitors, protease inhibitors such as patatin, cystatin, papain inhibitors; ricin, corn- Ribosome inactivating protein (RIP) such as RIP, abrin, saporin, bryodin; Steroid metabolic enzymes such as loxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; ion channel inhibitor such as sodium channel inhibitor and calcium channel inhibitor; juvenile hormone esterase Diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
In addition, as toxins expressed in such genetically modified plants, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxin proteins, VIP1, VIP2, VIP3, VIP3A and other insecticidal proteins Hybrid toxins, partially defective toxins, and modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073, etc. It is described in the patent literature. Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Diptera pests, and Lepidoptera pests.
　また、1つもしくは複数の殺虫性の害虫抵抗性遺伝子を含み、1つ又は複数の毒素を発現する遺伝子組換え植物は既に知られており、いくつかのものは市販されている。これら遺伝子組換え植物の例として、イールドガード（YieldGard）（商品名）（Cry1Ab毒素を発現するトウモロコシ品種）、イールドガードルートワーム（YieldGard Rootworm）（商品名）（Cry3Bb1毒素を発現するトウモロコシ品種）、イールドガードプラス（YieldGard Plus）（商品名）（Cry1AbとCry3Bb1毒素を発現するトウモロコシ品種）、ハーキュレックスI（Herculex I）（商品名）（Cry1Fa2毒素とグルホシネートへの耐性を付与するためのホスフィノトリシン N-アセチルトランスフェラーゼ（PAT）を発現するトウモロコシ品種）、NuCOTN33B（商品名）（Cry1Ac毒素を発現するワタ品種）、ボルガードI（Bollgard I）（商品名）（Cry1Ac毒素を発現するワタ品種）、ボルガードII（Bollgard II）（商品名）（Cry1AcとCry2Ab毒素を発現するワタ品種）、VIPCOT（商品名）（VIP毒素を発現するワタ品種）、ニューリーフ（NewLeaf）（商品名）（Cry3A毒素を発現するジャガイモ品種）、ネイチャーガード アグリシュアー GT アドバンテージ（NatureGard（商品名）Agrisure（商品名）GT Advantage）（GA21グリホサート耐性形質）、アグリシュアー CB アドバンテージ（Agrisure（商品名） CB Advantage）（Bt11コーンボーラー（CB）形質）、プロテクタ（Protecta）（商品名）等が挙げられる。 Also, transgenic plants containing one or more insecticidal pest resistance genes and expressing one or more toxins are already known, and some are commercially available. Examples of these genetically modified plants include YieldGard (trade name) (a corn variety expressing Cry1Ab toxin), YieldGard Rootworm (trade name) (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus (trade name) (a corn variety that expresses Cry1Ab and Cry3Bb1 toxins), Herculex I (trade name) (phosphino to confer resistance to Cry1Fa2 toxin and glufosinate Corn varieties expressing Tricine N-acetyltransferase (PAT), NuCOTN33B (trade name) (cotton varieties expressing Cry1Ac toxin), Volgaard I (Bollgard I) (trade name) (cotton varieties expressing Cry1Ac toxin), Bollgard II (trade name) (cotton varieties expressing Cry1Ac and Cry2Ab toxins), VIPCOT (trade name) (VIP poison) Cotton varieties that express element), NewLeaf (brand name) (potato varieties that express Cry3A toxin), Nature Guard Aglisher GT Advantage (NatureGard (brand name) Agrisure (brand name) GT Advantage) (GA21 glyphosate) Resistance traits), agrisure CB advantage (Agrisure (trade name) CB Advantage) (Bt11 corn borer (CB) trait), protector (trade name) and the like.
　上記作物には、遺伝子組換え技術を用いて、選択的な作用を有する抗病原性物質を産生する能力を付与されたものも含まれる。
　抗病原性物質としては、例えばPRタンパク（PRPs、EP-A-0392225に記載されている）；ナトリウムチャネル阻害剤、カルシウムチャネル阻害剤（ウイルスが産生するKP1、KP4、KP6毒素等が知られている）等のイオンチャネル阻害剤；スチルベンシンターゼ；ビベンジルシンターゼ；キチナーゼ；グルカナーゼ；ペプチド抗生物質、ヘテロ環を有する抗生物質、植物病害抵抗性に関与するタンパク因子（植物病害抵抗性遺伝子と呼ばれ、WO03/000906に記載されている）等の微生物が産生する物質等が挙げられる。このような抗病原性物質とそれを産生する遺伝子組換え植物は、EP-A-0392225、WO95/33818、EP-A-0353191等に記載されている。
　上記作物には、遺伝子組換え技術を用いて、油糧成分改質やアミノ酸含量増強形質などの有用形質を付与した作物も含まれる。例として、VISTIVE（商品名）（リノレン含量を低減させた低リノレン大豆）或いは、high-lysine（hig　hoil）　corn（リジン或いはオイル含有量を増量したコーン）等が挙げられる。 The crops include those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
Examples of anti-pathogenic substances include PR proteins (PRPs, described in EP-A-0392225); sodium channel inhibitors, calcium channel inhibitors (virus-produced KP1, KP4, KP6 toxins, etc.) Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes) And substances produced by microorganisms such as those described in WO03 / 000906). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.
The above-mentioned crops also include crops imparted with useful traits such as oil component modification and amino acid content enhancing traits using genetic recombination techniques. Examples include VISTIVE (trade name) (low linolenic soybean with reduced linolenic content) or high-lysine (hig hoil) corn (corn with increased lysine or oil content).
　更に、上記の古典的な除草剤形質或いは除草剤耐性遺伝子、殺虫性害虫抵抗性遺伝子、抗病原性物質産生遺伝子、油糧成分改質やアミノ酸含量増強形質などの有用形質について、これらを複数組み合わせたスタック品種も含まれる。 In addition, the above-mentioned classic herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, anti-pathogenic substance production genes, oil component modification and amino acid content enhancement traits Combined stack varieties are also included.
　式（１）で表される本発明化合物は、例えば以下の方法により製造することができる。
　製造法Ａ
Figure JPOXMLDOC01-appb-C000015
 ［式中、Ｑ、Ｒ６、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ７、Ｚ８、ｍ及びｎは前記と同じ意味を表す。］
　式（１）においてＡが水素原子である式（１－２）で表される本発明化合物と、式（３）[式中、Ａ１は水素原子以外の前記Ａと同じ意味を表し、Ｊａはハロゲン原子、－ＯＳＯ２Ｍｅ、－ＯＳＯ２ＣＦ３、－ＯＣ（Ｏ）Ｒ２等の脱離基を表し、Ｒ２は前記と同じ意味を表す。]で表される化合物とを、国際公開第２０１６／０９８８９９号記載の方法に準じて反応させることにより、式（１－１ａ）[式中、Ａ１は水素原子以外の前記Ａと同じ意味を表す。]で表される本発明化合物及び式（１－１ｂ）[式中、Ａ１は水素原子以外の前記Ａと同じ意味を表す。]で表される本発明化合物を製造することができる。また、反応条件によっては、式（１－１ａ）[式中、Ａ１は水素原子以外の前記Ａと同じ意味を表す。]で表される本発明化合物又は式（１－１ｂ）[式中、Ａ１は水素原子以外の前記Ａと同じ意味を表す。]で表される本発明化合物のどちらか一方のみを製造することもできる。
　式（３）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。 The compound of the present invention represented by the formula (1) can be produced, for example, by the following method.
Manufacturing method A
Figure JPOXMLDOC01-appb-C000015
 [Wherein, Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , m and n are the same as above. Means the same. ]
A compound of the present invention represented by formula (1-2) wherein A is a hydrogen atom in formula (1); and formula (3) [wherein A 1 represents the same meaning as A except for a hydrogen atom a represents a leaving group such as a halogen atom, —OSO 2 Me, —OSO 2 CF 3 , —OC (O) R 2 , and R 2 has the same meaning as described above. And a compound represented by the formula (1-1a) [wherein A 1 has the same meaning as A except for a hydrogen atom, by reacting with a compound represented by the method described in International Publication No. 2016/098899. To express. The compound of the present invention represented by the formula (1-1b) [wherein A 1 represents the same meaning as the above A except for a hydrogen atom. This invention compound represented by this can be manufactured. Depending on the reaction conditions, the formula (1-1a) [wherein A 1 represents the same meaning as A except for a hydrogen atom. The compound of the present invention represented by the formula (1-1b) [wherein A 1 represents the same meaning as the above A except for a hydrogen atom. It is also possible to produce only one of the compounds represented by the present invention.
Some of the compounds represented by formula (3) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
　製造法Ｂ
Figure JPOXMLDOC01-appb-C000016
 （式中、Ｒ６、Ｒ７、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ７、Ｚ８、ｍ及びｎは前記と同じ意味を表す。）
　式（１）においてＱが酸素原子であり、Ａが水素原子である式（１－２ｂ）で表される本発明化合物と、式（４）で表される化合物とを、国際公開第２０１６／０９８８９９号記載の方法に準じて反応させることにより、式（１）においてＱがＮＯＲ７であり、Ａが水素原子である式（１－２ａ）で表される本発明化合物を製造することが出来る。
　式（４）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。 Manufacturing method B
Figure JPOXMLDOC01-appb-C000016
 (In the formula, R 6 , R 7 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , m and n are It represents the same meaning as above.)
A compound of the present invention represented by the formula (1-2b) in which Q is an oxygen atom and A is a hydrogen atom in the formula (1), and a compound represented by the formula (4) are disclosed in WO2016 / By reacting according to the method described in No. 098899, the compound of the present invention represented by the formula (1-2a) in which Q is NOR 7 and A is a hydrogen atom in the formula (1) can be produced. .
Some of the compounds represented by formula (4) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
　製造法Ｃ
Figure JPOXMLDOC01-appb-C000017
 （式中、Ｒ６、Ｒ７、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ７、Ｚ８、ｍ及びｎは前記と同じ意味を表す。）
　式（１）においてＱがＮＯＲ７である式（１－３）[式中、Ａ３はＣ１～Ｃ６アルキルを表す。]で表される化合物を、国際公開第２０１６／０９８８９９号記載の方法に準じて反応させることにより、式（１）においてＱが酸素原子であり、Ａが水素原子である式（１－２ｂ）で表される本発明化合物を得ることができる。 Manufacturing method C
Figure JPOXMLDOC01-appb-C000017
 (In the formula, R 6 , R 7 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , m and n are It represents the same meaning as above.)
Formula (1-3) in which Q is NOR 7 in Formula (1) [wherein A 3 represents C 1 -C 6 alkyl. In the formula (1), Q is an oxygen atom, and A is a hydrogen atom (1-2b) This invention compound represented by these can be obtained.
　製造法Ｄ
Figure JPOXMLDOC01-appb-C000018
 （式中、Ａ３、Ｑ、Ｒ６、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ８、ｍ及びｎは前記と同じ意味を表す。）
　式（２－１ａ）で表される化合物と、式（５）[式中、Ｒ４１及びＪａは前記と同じ意味を表す。]で表される化合物とを、場合によっては塩基存在下、反応させることにより、式（１）においてＡがＡ３であり、Ｚ７が－ＯＲ４１である式（１－３ａ）で表される本発明化合物を製造することができる。
　ここで用いられる式（５）で表される化合物の量は、式（２－１ａ）で表される化合物１当量に対して、０．１～１００当量の範囲で用いることができる。
　本反応は、必要ならば、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、ｎ－ブチルリチウム、リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の塩基を使用することができる。使用することができる塩基の量は、式（２－１ａ）で表される化合物１当量に対して、０．１～１００当量の範囲で用いることができる。
　本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－８０℃から反応混合物の還流温度までの任意の温度を設定することができる。
　反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
　式（５）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。 Manufacturing method D
Figure JPOXMLDOC01-appb-C000018
 (In the formula, A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , m and n are the same as above. Represents the same meaning as
A compound represented by formula (2-1a) and formula (5) [wherein R 41 and J a represent the same meaning as described above. In some cases, the compound represented by formula (1-3a) wherein A is A 3 and Z 7 is —OR 41 in the presence of a base may be reacted with the compound represented by formula (1): This invention compound can be manufactured.
The amount of the compound represented by formula (5) used here can be used in the range of 0.1 to 100 equivalents relative to 1 equivalent of the compound represented by formula (2-1a).
If necessary, this reaction can be carried out using triethylamine, pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl). ) Bases such as amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate can be used. The amount of the base that can be used can be used in the range of 0.1 to 100 equivalents with respect to 1 equivalent of the compound represented by the formula (2-1a).
This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
Some of the compounds represented by formula (5) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
　製造法Ｅ
Figure JPOXMLDOC01-appb-C000019
 （式中、Ａ３、Ｑ、Ｒ６、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ８、ｍ及びｎは前記と同じ意味を表す。）
　式（２－１ｂ）で表される化合物と、式（５）[式中、Ｒ４１及びＪａは前記と同じ意味を表す。]で表される化合物とを、場合によっては塩基存在下、製造法Ｄと同様の方法に準じて反応させることにより、式（１）においてＡがＡ３であり、Ｚ７が－ＳＲ４１である式（１－３ｂ）で表される本発明化合物を製造することができる。 Manufacturing method E
Figure JPOXMLDOC01-appb-C000019
 (In the formula, A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , m and n are the same as above. Represents the same meaning as
A compound represented by formula (2-1b) and formula (5) [wherein R 41 and J a represent the same meaning as described above. In the formula (1), A is A 3 and Z 7 is —SR 41 by reacting the compound represented by A compound of the present invention represented by a certain formula (1-3b) can be produced.
　製造法Ｆ
Figure JPOXMLDOC01-appb-C000020
 （式中、Ａ１、Ｒ６、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ７、Ｚ８、ｍ及びｎは前記と同じ意味を表す。）
　式（１－１ａ）においてＲ７が水素原子である式（１－１ａ－１）で表される本発明化合物と、式（６）［式中、Ｒ７ｃは水素原子以外の前記Ｒ７と同じ意味を表し、Ｊａは前記と同じ意味を表す。]で表される化合物とを、場合によっては塩基の存在下、反応させることにより、式（１－１ａ－２）［式中、Ｒ７ｃは水素原子以外の前記Ｒ７と同じ意味を表す。］で表される本発明化合物を製造することができる。
　ここで用いられる式（６）で表される化合物の量は、式（１－１ａ－１）で表される化合物１当量に対して、０．１～１００当量の範囲で用いることができる。
　本反応は、必要ならば、トリエチルアミン、ピリジン、４－（ジメチルアミノ）ピリジン、１，８－ジアザビシクロ［５．４．０］－７－ウンデセン、ｎ－ブチルリチウム、リチウムジイソプロピルアミド、リチウムビス（トリメチルシリル）アミド、ナトリウムビス（トリメチルシリル）アミド、カリウムビス（トリメチルシリル）アミド、水素化ナトリウム、ナトリウムメトキシド、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム等の塩基を使用することができる。用いることのできる塩基の量は、式（１－１ａ－１）で表される化合物に対して、０．１～１００当量の範囲で用いることができる。
　本反応は、無溶媒で実施してもよいが、溶媒を用いてもよく、例えば、Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド、アセトニトリル、ジメチルスルホキシド、１，３－ジメチル－２－イミダゾリノン等の極性溶媒、メタノール、エタノール、プロパノール、２－プロパノール、エチレングリコール等のアルコール類、ジエチルエーテル、テトラヒドロフラン、ジフェニルエーテル等のエーテル類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、塩化メチレン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、ペンタン、ｎ－ヘキサン等の脂肪族炭化水素類が挙げられる。これらの溶媒は単独で用いても、これらの内の２種類以上を混合して用いてもよい。
　反応温度は、－８０℃から反応混合物の還流温度までの任意の温度を設定することがでる。
　反応時間は、反応基質の濃度、反応温度によって変化するが、通常５分から１００時間の範囲で任意に設定できる。
　式（６）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。 Manufacturing method F
Figure JPOXMLDOC01-appb-C000020
 (In the formula, A 1 , R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , m and n are It represents the same meaning as above.)
A compound of the present invention represented by formula (1-1a-1) in which R 7 is a hydrogen atom in formula (1-1a); and formula (6) [wherein R 7c represents the above R 7 other than a hydrogen atom; The same meaning is represented, and J a represents the same meaning as described above. The compound represented by formula (1-1a-2) is optionally reacted in the presence of a base, wherein R 7c represents the same meaning as R 7 other than a hydrogen atom. This invention compound represented by this can be manufactured.
The amount of the compound represented by the formula (6) used here can be used in the range of 0.1 to 100 equivalents relative to 1 equivalent of the compound represented by the formula (1-1a-1).
If necessary, this reaction can be carried out using triethylamine, pyridine, 4- (dimethylamino) pyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis (trimethylsilyl). ) Bases such as amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate can be used. The amount of the base that can be used can be used in the range of 0.1 to 100 equivalents with respect to the compound represented by the formula (1-1a-1).
This reaction may be carried out without a solvent, but a solvent may be used, for example, N, N-dimethylformamide, N, N-dimethylacetamide, acetonitrile, dimethyl sulfoxide, 1,3-dimethyl-2- Polar solvents such as imidazolinone, alcohols such as methanol, ethanol, propanol, 2-propanol and ethylene glycol, ethers such as diethyl ether, tetrahydrofuran and diphenyl ether, aromatic hydrocarbons such as benzene, toluene and xylene, methylene chloride Halogenated hydrocarbons such as chloroform and carbon tetrachloride, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used alone or as a mixture of two or more thereof.
The reaction temperature can be set to any temperature from −80 ° C. to the reflux temperature of the reaction mixture.
The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours.
Some of the compounds represented by formula (6) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
　製造法Ａ乃至製造法Ｆは、必要であれば窒素、アルゴン等の不活性ガス雰囲気下で実施しても良い。
　製造法Ａ乃至製造法Ｆにおいて、反応終了後の反応混合物は、直接濃縮、又は有機溶媒に溶解し、水洗後濃縮、又は氷水に投入、有機溶媒抽出後濃縮といった通常の後処理を行ない、目的の本発明化合物を得ることができる。また、精製の必要が生じたときには、再結晶、カラムクロマトグラフ、薄層クロマトグラフ、液体クロマトグラフ分取等の任意の精製方法によって分離、精製することができる。 Production method A to production method F may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.
In the production method A to the production method F, the reaction mixture after completion of the reaction is directly concentrated or dissolved in an organic solvent, concentrated after washing with water, or poured into ice water, and subjected to usual post-treatment such as concentration after extraction with an organic solvent. This invention compound can be obtained. Moreover, when the necessity for purification arises, it can be separated and purified by any purification method such as recrystallization, column chromatograph, thin layer chromatograph, liquid chromatographic fractionation and the like.
　製造法Ｄで用いられる式（２－１ａ）で表される化合物の或るものは公知化合物であり、例えば下記の反応式１の方法により製造することができる。
　反応式１
Figure JPOXMLDOC01-appb-C000021
 ［式中、Ａ３、Ｑ、Ｒ６、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ８、Ｘ３ａ、ｍ及びｎは前記と同じ意味を表す。］
　式（２－２）［式中、Ｊｂはハロゲン原子、－ＯＳＯ２Ｍｅ、－ＯＳＯ２ＣＦ３等の脱離基を表す。]で表される化合物と、式（７－１）[式中、Ｘ３ａは前記と同じ意味を表し、Ｒ１０２はＣ１～Ｃ６アルコキシを表し、ｓ４は０、１、２、３又は４の整数を表す。]で表される化合物又は式（７－２）[式中、Ｘ３ａは前記と同じ意味を表し、ｓ４は０、１、２、３又は４の整数を表す。]で表される化合物とを、例えばザ・ジャーナル・オブ・オーガニック・ケミストリー（The Journal of Organic Chemistry）１９９５年，６０巻，７５０８頁等に記載の公知の方法に準じて反応させることにより、式（３－１）[式中、Ｘ３ａ及びｓ４は上記と同じ意味を表す。]で表される化合物を製造することができる。
　次いで、式（３－１）で表される化合物を文献既知の公知の方法、例えば国際公開第２００４／０８７６８６号等に記載の方法に準じて反応させることにより、式（２－１ａ）で表される化合物を製造することができる。
　ここで用いられる式（２－２）で表される化合物は、例えば国際公開第２０１６／０９８８９９号に記載の公知の方法に準じて製造することができる。
　式（７－１）で表される化合物及び式（７－２）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。
　製造法Ｅで用いられる式（２－１ｂ）で表される化合物の或るものは公知化合物であり、例えば下記の反応式２の方法により製造することができる。 Some of the compounds represented by the formula (2-1a) used in the production method D are known compounds and can be produced, for example, by the method of the following reaction formula 1.
Reaction formula 1
Figure JPOXMLDOC01-appb-C000021
 [Wherein A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , X 3a , m and n represents the same meaning as described above. ]
Equation (2-2) wherein, J b represents a halogen atom, -OSO 2 Me, a leaving group such as -OSO 2 CF 3. A compound represented by formula (7-1): wherein X 3a represents the same meaning as described above, R 102 represents C 1 -C 6 alkoxy, and s4 represents 0, 1, 2, 3, or Represents an integer of 4. Or a compound represented by formula (7-2): wherein X 3a represents the same meaning as described above, and s4 represents an integer of 0, 1, 2, 3 or 4. And the like, for example, according to a known method described in The Journal of Organic Chemistry 1995, 60, 7508, etc. (3-1) [wherein X 3a and s4 represent the same meaning as described above. Can be produced.
Subsequently, the compound represented by the formula (3-1a) is reacted with the compound represented by the formula (3-1) according to a known method known in the literature, for example, a method described in International Publication No. 2004/087686. Can be produced.
The compound represented by the formula (2-2) used here can be produced according to a known method described in, for example, International Publication No. 2016/098899.
Some of the compound represented by formula (7-1) and the compound represented by formula (7-2) are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
Some of the compounds represented by the formula (2-1b) used in the production method E are known compounds and can be produced, for example, by the method of the following reaction formula 2.
　反応式２
Figure JPOXMLDOC01-appb-C000022
 ［式中、Ａ３、Ｑ、Ｒ６、Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１、Ｒ１２、Ｚ４、Ｚ５、Ｚ６、Ｚ８、ｍ及びｎは前記と同じ意味を表す。］
　式（２－２）[式中、Ｊｂは前記と同じ意味を表す。]で表される化合物と、式（８）[式中、Ｒ１０３はＣ１～Ｃ１０アルコキシカルボニル(Ｃ１～Ｃ６)アルキルを表す。]で表される化合物とを、例えば国際公開第２０１６／１２９６８４号等に記載の公知の方法に準じて反応させることにより、式（２－１ｃ）[式中、Ｒ１０３は上記と同じ意味を表す。]で表される化合物を製造することができる。
　次いで、式（２－１ｃ）で表される化合物を文献既知の公知の方法、例えば国際公開第２００９／０７２５８１号等に記載の方法に準じて反応させることにより、式（２－１ｂ）で表される化合物を製造することができる。
　ここで用いられる式（８）で表される化合物の或るものは公知化合物であり、一部は市販品として入手できる。また、それ以外のものも文献記載の公知の方法に準じて製造することができる。 Reaction formula 2
Figure JPOXMLDOC01-appb-C000022
 [In the formula, A 3 , Q, R 6 , R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , Z 4 , Z 5 , Z 6 , Z 8 , m and n are the same as above. Means the same. ]
Equation (2-2) wherein, J b are as defined above. And a compound represented by formula (8): wherein R 103 represents C 1 -C 10 alkoxycarbonyl (C 1 -C 6 ) alkyl. And the compound represented by formula (2-1c) [wherein R 103 has the same meaning as described above, by reacting the compound represented by formula (2-1c) with a compound represented by, for example, WO 2016/129684 To express. Can be produced.
Next, the compound represented by the formula (2-1c) is reacted according to a known method known in the literature, for example, the method described in International Publication No. 2009/072581, etc., to thereby represent the compound represented by the formula (2-1b). Can be produced.
Some of the compounds represented by the formula (8) used here are known compounds, and some of them are commercially available. Others can also be produced according to known methods described in the literature.
　反応式１及び反応式２は、必要であれば窒素、アルゴン等の不活性ガス雰囲気下で実施しても良い。
　これらの各反応においては、反応終了後、通常の後処理を行なうことにより製造法Ｄ及び製造法Ｅの原料化合物となる各々の製造中間体を得ることができる。
　また、これらの方法により製造された各々の製造中間体は、単離・精製することなく、それぞれそのまま次工程の反応に用いることもできる。 Reaction formula 1 and reaction formula 2 may be carried out in an inert gas atmosphere such as nitrogen or argon if necessary.
In each of these reactions, after the completion of the reaction, each of the production intermediates that are the raw material compounds of Production Method D and Production Method E can be obtained by carrying out ordinary post-treatment.
In addition, each production intermediate produced by these methods can be used as it is in the subsequent step without isolation and purification.
　これらの方法を用いて製造できる本発明に包含される式（１）で表されるケトン若しくはオキシム化合物としては、具体的に例えば下記の[１]－１～[１]－１４３の構造式で表される化合物が挙げられる。但し、[１]－１～[Ｉ]－１４３の構造式で表される化合物は例示のためのものであって、本発明に包含されるケトン若しくはオキシム化合物はこれらのみに限定されるものではない。
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
 Specific examples of the ketone or oxime compound represented by the formula (1) included in the present invention that can be produced by using these methods include the following structural formulas [1] -1 to [1] -143. And the compounds represented. However, the compounds represented by the structural formulas [1] -1 to [I] -143 are for illustrative purposes, and the ketone or oxime compounds included in the present invention are not limited to these. Absent.
Figure JPOXMLDOC01-appb-C000023
Figure JPOXMLDOC01-appb-C000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000026
　ここで、[１]－１～[１]－１４３の構造式に於いてＡ、Ｚ４及びＲ４１で表される置換基の具体的な組み合わせの例としては、具体的に例えば第１表及び第２表に示す組み合わせが挙げられる。但し、第１表及び第２表の組み合わせは例示のためのものであって、本発明に包含されるケトン若しくはオキシム化合物のＡ、Ｚ４及びＲ４１で表される置換基の具体的な組み合わせはこれらのみに限定されるものではない。 Here, specific examples of combinations of substituents represented by A, Z 4 and R 41 in the structural formulas [1] -1 to [1] -143 include, for example, Table 1 And combinations shown in Table 2. However, the combinations of Tables 1 and 2 are for illustrative purposes, and are specific combinations of substituents represented by A, Z 4 and R 41 of the ketone or oxime compound included in the present invention. Is not limited to these.
第１表
　尚、表中、Ｍｅと記載される置換基はメチル基を表し、以下同様に、Ｅｔとの記載はエチル基を、ｎ－Ｐｒ及びＰｒ－ｎはノルマルプロピル基を、ｉ－Ｐｒ及びＰｒ－ｉはイソプロピル基を、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピル基を、ｎ－Ｂｕ及びＢｕ－ｎはノルマルブチル基を、ｓ－Ｂｕ及びＢｕ－ｓはセカンダリーブチル基を、ｉ－Ｂｕ及びＢｕ－ｉはイソブチル基を、ｔ－Ｂｕ及びＢｕ－ｔはターシャリーブチル基を、ｃ－Ｂｕ及びＢｕ－ｃはシクロブチル基を、ｎ－Ｐｅｎ及びＰｅｎ－ｎはノルマルペンチル基を、ｃ－Ｐｅｎ及びＰｅｎ－ｃはシクロペンチル基を、ｎ－Ｈｅｘ及びＨｅｘ－ｎはノルマルヘキシル基を、ｃ－Ｈｅｘ及びＨｅｘ－ｃはシクロヘキシル基を、ｎ－Ｏｃｔ及びＯｃｔ－ｎはノルマルオクチル基を、Ｐｈはフェニル基を、Ｂｎはベンジル基を、「＝」は２重結合を、「≡」は３重結合をそれぞれ表す。 In the table, the substituent described as Me represents a methyl group, and similarly, the description of Et represents an ethyl group, n-Pr and Pr-n represent normal propyl groups, and i-Pr. And Pr-i are isopropyl groups, c-Pr and Pr-c are cyclopropyl groups, n-Bu and Bu-n are normal butyl groups, s-Bu and Bu-s are secondary butyl groups, i- Bu and Bu-i are isobutyl groups, t-Bu and Bu-t are tertiary butyl groups, c-Bu and Bu-c are cyclobutyl groups, n-Pen and Pen-n are normal pentyl groups, c -Pen and Pen-c are cyclopentyl groups, n-Hex and Hex-n are normal hexyl groups, c-Hex and Hex-c are cyclohexyl groups, and n-Oct and Oct-n are normal octyl groups. Ph represents a phenyl group, Bn represents a benzyl group, “=” represents a double bond, and “≡” represents a triple bond.
　表中、Ｄ２－１０８、Ｄ３－３ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－５８ｂ、Ｄ３－６０ａ、Ｄ３－６０ｂ及びＤ３－６５ａとの記載は、下記の構造を表す。
Figure JPOXMLDOC01-appb-C000027
 　上記の構造式において記載した番号は、置換基Ｘ３の置換位置を表すものであり、例えば、表中、「Ｄ３－１８ｂ［６－Ｃｌ］」との記載は「６－クロロベンゾオキサゾール－２－イル基」を表す。尚、［－］は無置換を表す。 In the table, D2-108, D3-3a, D3-18b, D3-21a, D3-21b, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-58b , D3-60a, D3-60b and D3-65a represent the following structures.
Figure JPOXMLDOC01-appb-C000027
 The numbers described in the above structural formula represent the substitution position of the substituent X 3. For example, in the table, the description “D3-18b [6-Cl]” is “6-chlorobenzoxazole-2 Represents an “-yl group”. [-] Represents no substitution.
　また、表中、Ａ２ａ、Ａ２ｂ、Ａ２ｃ、Ａ２ｄ、Ａ２ｅ、Ａ２ｆ、Ａ２ｇ及びＡ２ｈとの記載は、下記の構造を表し、
Figure JPOXMLDOC01-appb-C000028
 　上記の構造式において記載した番号は、置換基Ｚａ、Ｚｂ及びＺｆの置換位置を表すものであり、例えば、表中、「Ａ２ａ［４－Ｃｌ］」との記載は「４－クロロベンゾイル基」を表す。尚、括弧書きのないものは無置換を表す。
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000077
Figure JPOXMLDOC01-appb-T000078
Figure JPOXMLDOC01-appb-T000079
Figure JPOXMLDOC01-appb-T000080
Figure JPOXMLDOC01-appb-T000081
Figure JPOXMLDOC01-appb-T000082
 In the table, the descriptions A2a, A2b, A2c, A2d, A2e, A2f, A2g and A2h represent the following structures:
Figure JPOXMLDOC01-appb-C000028
 The numbers described in the above structural formulas represent the substitution positions of the substituents Z a , Z b and Z f. Represents a benzoyl group. In addition, those without parentheses indicate no substitution.
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000077
Figure JPOXMLDOC01-appb-T000078
Figure JPOXMLDOC01-appb-T000079
Figure JPOXMLDOC01-appb-T000080
Figure JPOXMLDOC01-appb-T000081
Figure JPOXMLDOC01-appb-T000082
第２表
　尚、表中、Ｍｅと記載される置換基はメチル基を表し、以下同様に、Ｅｔとの記載はエチル基を、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピル基を、Ｐｈはフェニル基をそれぞれ表し、
　表中、Ｄ２－１０８及びＤ３－６０ｂとの記載は、それぞれ下記の構造を表し、
Figure JPOXMLDOC01-appb-C000083
 　上記の構造式において記載した番号は、置換基Ｚｆ及びＸ３の置換位置を表すものであり、例えば、表中、「Ｄ３－６０ｂ［６－Ｃｌ］」との記載は「６－キノキサリン－２－イル基」を表し、
　表中、Ａ３ａ、Ａ３ｂ、Ａ３ｃ、Ａ３ｄ及びＡ３ｅとの記載は、それぞれ下記の構造を表す。
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-T000085
Figure JPOXMLDOC01-appb-T000086
Figure JPOXMLDOC01-appb-T000087
Figure JPOXMLDOC01-appb-T000088
Figure JPOXMLDOC01-appb-T000089
Figure JPOXMLDOC01-appb-T000090
Figure JPOXMLDOC01-appb-T000091
Figure JPOXMLDOC01-appb-T000092
Figure JPOXMLDOC01-appb-T000093
Figure JPOXMLDOC01-appb-T000094
Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000099
Figure JPOXMLDOC01-appb-T000100
Figure JPOXMLDOC01-appb-T000101
Figure JPOXMLDOC01-appb-T000102
Figure JPOXMLDOC01-appb-T000103
Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000105
Figure JPOXMLDOC01-appb-T000106
Figure JPOXMLDOC01-appb-T000107
Figure JPOXMLDOC01-appb-T000108
Figure JPOXMLDOC01-appb-T000109
Figure JPOXMLDOC01-appb-T000110
Figure JPOXMLDOC01-appb-T000111
Figure JPOXMLDOC01-appb-T000112
Figure JPOXMLDOC01-appb-T000113
Figure JPOXMLDOC01-appb-T000114
Figure JPOXMLDOC01-appb-T000115
Figure JPOXMLDOC01-appb-T000116
Figure JPOXMLDOC01-appb-T000117
 Table 2 In the table, the substituent represented by Me represents a methyl group, and similarly, Et represents an ethyl group, c-Pr and Pr-c represent a cyclopropyl group, and Ph represents a phenyl group. Each represents a group,
In the table, the descriptions D2-108 and D3-60b represent the following structures, respectively.
Figure JPOXMLDOC01-appb-C000083
 Number described in the above structural formula is intended to represent the substitution position of the substituent Z f and X 3, for example, in the table, the description "D3-60b [6-Cl]""6-quinoxaline - 2-yl group "
In the table, the descriptions A3a, A3b, A3c, A3d, and A3e represent the following structures, respectively.
Figure JPOXMLDOC01-appb-C000084
Figure JPOXMLDOC01-appb-T000085
Figure JPOXMLDOC01-appb-T000086
Figure JPOXMLDOC01-appb-T000087
Figure JPOXMLDOC01-appb-T000088
Figure JPOXMLDOC01-appb-T000089
Figure JPOXMLDOC01-appb-T000090
Figure JPOXMLDOC01-appb-T000091
Figure JPOXMLDOC01-appb-T000092
Figure JPOXMLDOC01-appb-T000093
Figure JPOXMLDOC01-appb-T000094
Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000099
Figure JPOXMLDOC01-appb-T000100
Figure JPOXMLDOC01-appb-T000101
Figure JPOXMLDOC01-appb-T000102
Figure JPOXMLDOC01-appb-T000103
Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000105
Figure JPOXMLDOC01-appb-T000106
Figure JPOXMLDOC01-appb-T000107
Figure JPOXMLDOC01-appb-T000108
Figure JPOXMLDOC01-appb-T000109
Figure JPOXMLDOC01-appb-T000110
Figure JPOXMLDOC01-appb-T000111
Figure JPOXMLDOC01-appb-T000112
Figure JPOXMLDOC01-appb-T000113
Figure JPOXMLDOC01-appb-T000114
Figure JPOXMLDOC01-appb-T000115
Figure JPOXMLDOC01-appb-T000116
Figure JPOXMLDOC01-appb-T000117
　ここで、［１］－１～［１］－１４３の構造式で表される本発明に包含されるケトン若しくはオキシム化合物の製造中間体の例を第３表及び第４表に示すが、本発明化合物の製造中間体はこれらのみに限定されるものではない。
　尚、表中、Ｍｅとの記載はメチル基を表し、以下同様に、Ｅｔはエチル基を、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピル基をそれぞれ表す。 Here, examples of production intermediates of ketones or oxime compounds represented by the structural formulas [1] -1 to [1] -143 are shown in Tables 3 and 4. The production intermediate of the inventive compound is not limited to these.
In the table, the term Me represents a methyl group, and similarly, Et represents an ethyl group, and c-Pr and Pr-c represent a cyclopropyl group, respectively.
　〔第３表〕
Figure JPOXMLDOC01-appb-C000118
Figure JPOXMLDOC01-appb-T000119
 [Table 3]
Figure JPOXMLDOC01-appb-C000118
Figure JPOXMLDOC01-appb-T000119
　〔第４表〕
Figure JPOXMLDOC01-appb-C000120
Figure JPOXMLDOC01-appb-T000121
 [Table 4]
Figure JPOXMLDOC01-appb-C000120
Figure JPOXMLDOC01-appb-T000121
　本発明に包含される式（１）で表される化合物のうちで、常法に従って酸付加塩にすることができるものは、例えば、フッ化水素酸、塩酸、臭化水素酸、沃化水素酸等のハロゲン化水素酸の塩、硝酸、硫酸、燐酸、塩素酸、過塩素酸等の無機酸の塩、メタンスルホン酸、エタンスルホン酸、トリフルオロメタンスルホン酸、ベンゼンスルホン酸、p-トルエンスルホン酸等のスルホン酸の塩、ギ酸、酢酸、プロピオン酸、トリフルオロ酢酸、フマール酸、酒石酸、蓚酸、マレイン酸、リンゴ酸、コハク酸、安息香酸、マンデル酸、アスコルビン酸、乳酸、グルコン酸、クエン酸等のカルボン酸の塩又はグルタミン酸、アスパラギン酸等のアミノ酸の塩とすることができる。
　或いは、本発明に包含される式（１）で表される化合物のうちで、常法に従って金属塩にすることができるものは、例えば、リチウム、ナトリウム、カリウムといったアルカリ金属の塩、カルシウム、バリウム、マグネシウムといったアルカリ土類金属の塩又はアルミニウムの塩とすることができる。 Among the compounds represented by the formula (1) included in the present invention, those that can be converted into acid addition salts according to a conventional method are, for example, hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydrogen iodide. Hydrohalic acid salts such as acids, inorganic acid salts such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfone Salts of sulfonic acids such as acids, formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid A salt of a carboxylic acid such as an acid or a salt of an amino acid such as glutamic acid or aspartic acid can be used.
Alternatively, among the compounds represented by the formula (1) included in the present invention, those that can be converted into a metal salt according to a conventional method are, for example, alkali metal salts such as lithium, sodium, and potassium, calcium, and barium. , An alkaline earth metal salt such as magnesium, or an aluminum salt.
　本発明化合物は水田用の除草剤として、湛水下の土壌処理及び茎葉処理のいずれの処理方法においても使用できる。
　また、本発明化合物は、畑地および果樹園用の除草剤として、土壌処理、土壌混和処理及び茎葉処理のいずれの処理方法においても使用できる。
　さらに、本発明化合物は、水田、畑地及び果樹園等の農園芸分野以外に芝地、運動場、空地、道路脇、及び線路端等非農耕地において、土壌処理、土壌混和処理及び茎葉処理のいずれの処理方法においても使用できる。 The compound of the present invention can be used as a herbicide for paddy fields in any treatment method of soil treatment and foliage treatment under flooded water.
In addition, the compound of the present invention can be used as a herbicide for upland fields and orchards in any treatment method of soil treatment, soil admixture treatment, and foliage treatment.
Further, the compound of the present invention can be used for any of soil treatment, soil mixing treatment and foliage treatment in non-agricultural lands such as lawns, playgrounds, open spaces, roadsides, and track ends in addition to the fields of agriculture and horticulture such as paddy fields, upland fields and orchards. It can also be used in the processing method.
　本発明化合物を除草剤として施用するにあたっては、通常適当な固体担体又は液体担体と混合し、更に所望により界面活性剤、浸透剤、展着剤、増粘剤、凍結防止剤、結合剤、固結防止剤、崩壊剤及び分解防止剤等を添加して、水和剤、乳剤、フロアブル剤、ドライフロアブル剤、液剤、粉剤、粒剤又はゲル剤等任意の剤型の製剤にて実用に供することができる。また、省力化及び安全性向上の観点から、上記任意の剤型の製剤を水溶性包装体に封入して供することもできる。 In applying the compound of the present invention as a herbicide, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, a penetrating agent, a spreading agent, a thickening agent, an antifreezing agent, a binder, a solid carrier. Add anti-caking agent, disintegrant, anti-decomposition agent, etc., and put to practical use in any dosage form such as wettable powder, emulsion, flowable, dry flowable, liquid, powder, granule or gel. be able to. In addition, from the viewpoint of labor saving and safety improvement, the preparation of any dosage form can be enclosed in a water-soluble package.
　固体担体としては、例えば石英、カオリナイト、パイロフィライト、セリサイト、タルク、ベントナイト、酸性白土、アタパルジャイト、ゼオライト及び珪藻土等の天然鉱物質類、炭酸カルシウム、硫酸アンモニウム、硫酸ナトリウム及び塩化カリウム等の無機塩類、合成珪酸並びに合成珪酸塩が挙げられる。
　液体担体としては、例えばエチレングリコール、プロピレングリコール及びイソプロパノール等のアルコール類、キシレン、アルキルベンゼン及びアルキルナフタレン等の芳香族炭化水素類、ブチルセロソルブ等のエーテル類、シクロヘキサノン等のケトン類、γ－ブチロラクトン等のエステル類、Ｎ－メチルピロリドン、Ｎ－オクチルピロリドン等の酸アミド類、大豆油、ナタネ油、綿実油及びヒマシ油等の植物油並びに水が挙げられる。
　これら固体及び液体担体は、単独で用いても２種以上を併用してもよい。 Examples of solid carriers include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and other minerals, calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicates.
Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. And acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.
These solid and liquid carriers may be used alone or in combination of two or more.
　界面活性剤としては、例えばポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルフェニルエーテル、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリオキシエチレン脂肪酸エステル、ソルビタン脂肪酸エステル及びポリオキシエチレンソルビタン脂肪酸エステル等のノニオン性界面活性剤、アルキル硫酸塩、アルキルベンゼンスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、ポリオキシエチレンアルキルアリールエーテル硫酸及び燐酸塩、ポリオキシエチレンスチリルフェニルエーテル硫酸及び燐酸塩、ポリカルボン酸塩及びポリスチレンスルホン酸塩等のアニオン性界面活性剤、アルキルアミン塩及びアルキル４級アンモニウム塩等のカチオン性界面活性剤並びにアミノ酸型及びベタイン型等の両性界面活性剤が挙げられる。
　これら界面活性剤の含有量は、特に限定されるものではないが、本発明の製剤１００質量部に対し、通常０．０５から２０質量部の範囲が望ましい。また、これら界面活性剤は、単独で用いても２種以上を併用してもよい。 Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactant such as fatty acid ester, alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, Salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene polystyrene Anionic surfactants such as phenyl ether sulfate and phosphate, polycarboxylate and polystyrene sulfonate, cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, and amphoteric interfaces such as amino acid type and betaine type An activator is mentioned.
The content of these surfactants is not particularly limited, but is usually in the range of 0.05 to 20 parts by mass with respect to 100 parts by mass of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.
　本発明化合物は必要に応じて製剤又は散布時に他種の除草剤、各種殺虫剤、殺菌剤、植物生長調節剤又は共力剤等と混合施用してもよい。
　特に、他の除草剤と混合施用することにより、施用薬量の減少による低コスト化、混合薬剤の相乗作用による殺草スペクトラムの拡大や、より高い殺草効果が期待できる。この際、同時に複数の公知除草剤との組み合わせも可能である。
　本発明化合物の施用薬量は適用場面、施用時期、施用方法、栽培作物等により差異はあるが一般には有効成分量としてヘクタール（ｈａ）当たり０．００５から５０ｋｇ程度が適当である。 The compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.
In particular, when mixed with other herbicides, cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected. At this time, a combination with a plurality of known herbicides is also possible.
The application dose of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops, etc., but generally an amount of 0.005 to 50 kg per hectare (ha) is appropriate as the amount of active ingredient.
　次に本発明化合物を用いる場合の製剤の配合例を示す。但し本発明の配合例は、これらのみに限定されるものではない。尚、以下の配合例において「部」は質量部を意味する。 Next, formulation examples of the preparation when the compound of the present invention is used are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “part” means part by mass.
水和剤
本発明化合物　　　　　　　　０．１～８０部
固体担体　　　　　　　　　　５～９８．９部
界面活性剤　　　　　　　　　　　１～１０部
その他　　　　　　　　　　　　　０～　５部
　その他として、例えば固結防止剤、分解防止剤等が挙げられる。 Wettable compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, anti-caking agents and decomposition inhibitors.
乳　剤
本発明化合物　　　　　　　　０．１～３０部
液体担体　　　　　　　　　　　４５～９５部
界面活性剤　　　　　　　　　４．９～１５部
その他　　　　　　　　　　　　　０～１０部
　その他として、例えば展着剤、分解防止剤等が挙げられる。 Emulsified compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents and decomposition inhibitors.
フロアブル（ｆｌｏｗａｂｌｅ）剤
本発明化合物　　　　　　　　０．１～７０部
液体担体　　　　　　　　１５～９８．８９部
界面活性剤　　　　　　　　　　　１～１２部
その他　　　　　　　　　　０．０１～３０部
　その他として、例えば凍結防止剤、増粘剤等が挙げられる。 Flowable agent compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts Others include, for example, anti-freezing agents, thickeners, etc. It is done.
ドライフロアブル（ｄｒｙ　ｆｌｏｗａｂｌｅ）剤
本発明化合物　　　　　　　　０．１～９０部
固体担体　　　　　　　　　　０～９８．９部
界面活性剤　　　　　　　　　　　１～２０部
その他　　　　　　　　　　　　　０～１０部
　その他として、例えば結合剤、分解防止剤等が挙げられる。 Dry flowable agent compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors, etc. .
液　剤
本発明化合物　　　　　　　０．０１～７０部
液体担体　　　　　　　　２０～９９．９９部
その他　　　　　　　　　　　　　０～１０部
　その他として、例えば凍結防止剤、展着剤等が挙げられる。 Liquid Compound of the Present Invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts Others include, for example, antifreezing agents, spreading agents and the like.
粒　剤
本発明化合物　　　　　　　０．０１～８０部
固体担体　　　　　　　　１０～９９．９９部
その他　　　　　　　　　　　　　０～１０部
　その他として、例えば結合剤、分解防止剤等が挙げられる。 Granules Invention compound 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors and the like.
粉　剤
本発明化合物　　　　　　　０．０１～３０部
固体担体　　　　　　　　６５～９９．９９部
その他　　　　　　　　　　　　　０～１０部
　その他として、例えばドリフト防止剤、分解防止剤等が挙げられる。
　使用に際しては上記製剤をそのままで、又は水で１～１００００倍に希釈して散布する。 Powder Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 10 parts Others include, for example, drift inhibitors and decomposition inhibitors.
In use, the preparation is sprayed as it is or diluted 1 to 10000 times with water.
　製剤例
　次に具体的に本発明化合物を有効成分とする農薬製剤例を示すがこれらのみに限定されるものではない。尚、以下の配合例において「部」は質量部を意味する。 Formulation Examples Next, specific examples of agrochemical formulations containing the compound of the present invention as an active ingredient are shown, but the invention is not limited thereto. In the following formulation examples, “part” means part by mass.
〔配合例１〕水和剤
　本発明化合物Ｎｏ．１－００１　　　　　　２０部
　パイロフィライト　　　　　　　　　　　　７６部
　ソルポール５０３９　　　　　　　　　　　　２部
　（アニオン性界面活性剤：東邦化学工業（株）商品名）
　カープレックス＃８０　　　　　　　　　　　２部
　（合成含水珪酸：塩野義製薬（株）商品名）
　以上を均一に混合粉砕して水和剤とする。 [Formulation Example 1] Wetting Agent Compound No. 1-001 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (Anionic surfactant: Toho Chemical Co., Ltd. trade name)
Carplex # 80 2 parts (Synthetic hydrous silicate: Shionogi Pharmaceutical Co., Ltd. trade name)
The above is uniformly mixed and ground to obtain a wettable powder.
〔配合例２〕乳　剤
　本発明化合物Ｎｏ．１－００１　　　　　　　５部
　キシレン　　　　　　　　　　　　　　　　７５部
　Ｎ－メチルピロリドン　　　　　　　　　　１５部
　ソルポール２６８０　　　　　　　　　　　　５部
（アニオン性界面活性剤：東邦化学工業（株）商品名）
　以上を均一に混合して乳剤とする。 [Composition Example 2] Milk Compound No. of the present invention. 1-001 5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (anionic surfactant: Toho Chemical Industries, Ltd. trade name)
The above is uniformly mixed to obtain an emulsion.
〔配合例３〕フロアブル剤
　本発明化合物Ｎｏ．１－００１　　　　　　２５部
　アグリゾールＳ－７１０　　　　　　　　　１０部
　（非イオン性界面活性剤：花王（株）商品名）
　ルノックス１０００Ｃ　　　　　　　　　０．５部
　（アニオン性界面活性剤：東邦化学工業（株）商品名）
　キサンタンガム　　　　　　　　　　　０．０２部
　水　　　　　　　　　　　　　　　　６４．４８部
　以上を均一に混合した後、湿式粉砕してフロアブル剤とする。 [Composition Example 3] Flowable Agent Compound No. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: trade name of Kao Corporation)
Lnox 1000C 0.5 part (anionic surfactant: Toho Chemical Co., Ltd. trade name)
Xanthan gum 0.02 parts Water 64.48 parts After uniformly mixing the above, wet milling to obtain a flowable agent.
〔配合例４〕ドライフロアブル剤
　本発明化合物Ｎｏ．１－００１　　　　　　７５部
　ハイテノールＮＥ－１５　　　　　　　　　　５部
　（アニオン性界面活性剤：第一工業製薬（株）商品名）
　バニレックスＮ　　　　　　　　　　　　　１０部
　（アニオン性界面活性剤：日本製紙（株）商品名）
　カープレックス＃８０　　　　　　　　　　１０部
　（合成含水珪酸：塩野義製薬（株）商品名）
　以上を均一に混合粉砕した後、少量の水を加えて撹拌混合捏和し、押出式造粒機で造粒し、乾燥してドライフロアブル剤とする。 [Composition Example 4] Dry flowable agent Compound No. 1-001 75 parts Hightenol NE-15 5 parts (Anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd. trade name)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80 10 parts (Synthetic hydrous silicic acid: Shionogi Pharmaceutical Co., Ltd. trade name)
After uniformly mixing and pulverizing the above, a small amount of water is added and stirred and kneaded, granulated with an extrusion granulator, and dried to obtain a dry flowable agent.
〔配合例５〕粒　剤
　本発明化合物Ｎｏ．１－００１　　　　　　　１部
　ベントナイト　　　　　　　　　　　　　　５５部
　タルク　　　　　　　　　　　　　　　　　４４部
　以上を均一に混合粉砕した後、少量の水を加えて撹拌混合捏和し、押出式造粒機で造粒し、乾燥して粒剤とする。 [Formulation Example 5] Granule The present compound No. 1-001 1 part Bentonite 55 parts Talc 44 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed with stirring, kneaded, granulated with an extrusion granulator, and dried to form granules.
　本発明化合物は必要に応じて製剤または散布時に他種の除草剤、各種殺虫剤、殺菌剤、植物生長調節剤又は共力剤等と混合施用しても良い。
　特に、他の除草剤と混合施用することにより、施用薬量の減少による低コスト化、混合薬剤の相乗作用による殺草スペクトラムの拡大や、より高い殺草効果が期待できる。この際、同時に複数の公知除草剤との組み合わせも可能である。 The compound of the present invention may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists, and the like, as necessary, during formulation or spraying.
In particular, when mixed with other herbicides, cost reduction due to a decrease in the amount of applied medicine, expansion of the herbicidal spectrum due to the synergistic action of the mixed drugs, and higher herbicidal effects can be expected. At this time, a combination with a plurality of known herbicides is also possible.
　本発明化合物と混合使用されるのに好ましい除草剤としては、例えば、アセトクロール（acetochlor）、アシフルオルフェン（acifluorfen）、アクロニフェン（aclonifen）、アラクロール（alachlor）、アロキシジム（alloxydim）、アロキシジムナトリウム（alloxydim-sodium）、アメトリン（ametryn）、アミカルバソン（amicarbazone）、アミドスルフロン（amidosulfuron）、アミノシクロピラクロール（aminocyclopirachlor)、アミノシクロピラクロールの塩およびエステル（aminocyclopirachlor-salts and esters)、アミノピラリド（aminopyralid）、アミノピラリドの塩およびエステル（aminopyralid-salts and esters）、アミプロホスメチル（amiprophos-methyl）、アミトロール（amitrol）、アニロホス（anilofos）、アシュラム（asulam）、アトラジン（atrazine）、アザフェニジン（azafenidin）、アジムスルフロン（azimsulfuron）、ベフルブタミド（beflubutamid）、ベナゾリンエチル（benazolin-ethyl）、ベンカルバゾン（bencarbazone）、ベンフルラリン（benfluralin、benefin）、ベンフレセート（benfuresate）、ベンスルフロンメチル（bensulfuron-methyl）、ベンスリド（bensulide）、ベンタゾン（bentazone）、ベンタゾンナトリウム（bentazone-sodium）、ベンタゾンの塩（bentazone-salts）、ベンチオカーブ（benthiocarb）、ベンズフェンジゾン（benzfendizone）、ベンゾビシクロン（benzobicyclon）、ベンゾフェナップ（benzofenap）、ビアラホス（bialaphos）、ビアラホスナトリウム（bialaphos-sodium）、ビシクロピロン（bicyclopyrone）、ビフェノックス（bifenox）、ビスピリバック（bispyribac）、ビスピリバックナトリウム（bispyribac-sodium）、ブロマシル（bromacil）、ブロモブチド（bromobutide）、ブロモフェノキシム（bromofenoxim）、ブロモキシニル（bromoxynil）、ブロモキシニルの塩およびエステル（bromoxynil-salts and esters）、ブタクロール（butachlor）、ブタフェナシル（butafenacil）、ブタミホス（butamifos）、ブテナクロール（butenachlor）、ブトラリン（butralin）、ブトロキシジム（butroxydim）、ブチレート（butylate）、カフェンストロール（cafenstrole）、カルベタミド（carbetamide）、カルフェントラゾンエチル（carfentrazone-ethyl）、クロメトキシフェン（chlomethoxyfen）、クロメトキシニル（chlomethoxynil）、クロランベン（chloramben）、クロランベンの塩およびエステル（chloramben-salts and esters）、クロランスラムメチル（chloransulam-methyl）、クロルフルレノールメチル（chlorflurenol-methyl）、クロリダゾン（chloridazon）、クロリムロンエチル（chlorimuron-ethyl）、クロロブロムロン（chlorobromuron）、クロロトルロン（chlorotoluron）、クロロクスロン（chloroxuron）、クロルフタリム（chlorphtalim）、クロルプロファム（chlorpropham）、クロロIPC（chlorpropham）、クロルスルフロン（chlorsulfuron）、クロルタルジメチル（chlorthal-dimethyl）、クロルチアミド（chlorthiamid）、シニドンエチル（cinidon-ethyl）、シンメスリン（cinmethylin）、シノスルフロン（cinosulfuron）、クレトジム（clethodim）、クロジナホップ（clodinafop）、クロジナホッププロパルギル（clodinafop-propargyl）、クロマゾン（clomazone）、クロメプロップ（clomeprop）、クロピラリド（clopyralid）、クロピラリドの塩およびエステル（clopyralid-salts and esters）、CNP、クミルロン（cumyluron）、シアナジン（cyanazin）、シクロエート（cycloate）、シクロピリモレート（cyclopyrimorate、SW-065（試験名)、シクロスルファムロン（cyclosulfamuron）、シクロキシジム（cycloxydim）、シハロホップブチル（cyhalofop-butyl）、DAH-500（試験名）、ダラポン（dalapon）、ダゾメット（dazomet）、デスメディファム（desmedipham）、デスメトリン（desmetryn）、ダイカンバ（dicamba）、ダイカンバの塩およびエステル（dicamba-salts and esters）、ジクロベニル（dichlobenil）、ジクロホップ（diclofop）、ジクロホップメチル（diclofop-methyl）、ジクロルプロップ（dichlorprop）、ジクロルプロップの塩およびエステル（dichlorprop-salts and esters）、Pジクロルプロップ（dichlorprop-P）、Pジクロルプロップの塩およびエステル（dichlorprop-P-salts and esters）、ジクロスラム（diclosulam）、ジフェンゾコート（difenzoquat）、ジフルフェニカン（diflufenican）、ジフルフェンゾピル（diflufenzopyr）、ジフルフェンゾピルナトリウム（diflufenzopyr-sodium）、ジメピペレート（dimepiperate）、ジメタメトリン（dimethametryn）、ジメタクロール（dimethachlor）、ジメテナミド（dimethenamid）、Pジメテナミド（dimethenamid-p）、ジメシピン（dimethipin）、ジニトロアミン（dinitramine）、ジノセブ（dinoseb）、ジノテルブ（dinoterb）、DNOC、ジフェナミド（diphenamid）、ジクワット（diquqt）、ジチオピル（dithiopyl）、ジウロン（diuron）、DSMA、ダイムロン（dymron）、エンドタール（endothal）、EPTC、エスプロカルブ（esprocarb）、エタルフルラリン（ethalfluralin）、エタメトスルフロンメチル（ethametsulfuron-methyl）、エトフメセート（ethofumesate）、エトベンザニド（etobenzanid）、エトキシスルフロン（ethoxysulfuron）、フラザスルフロン（flazasulfuron）、フェノキサプロップ（fenoxaprop）、フェノキサプロップエチル（fenoxaprop-ethyl）、フェノキサスルホン（fenoxasulfone）、フェンキノトリオン（fenquionotrion）、フェントラザミド（fentrazamide）、フラムプロップ（flamprop）、フラザスルフロン（flazasulfuron）、フロラスラム（florasulam）、フルアジホップ（fluazifop）、フルアジホップブチル（fluazifop-butyl）、フルアゾレート（fluazolate）、フルカルバゾンナトリウム（flucarbazone-sodium）、フルセトスルフロン(flucetosulfuron)、フルクロラリン（flucloralin）、フルフェナセット（flufenacet）、フルフェンピルエチル（flufenpyl-ethyl）、フルメツラム（flumetsulam）、フルミクロラックペンチル（flumiclorac-pentyl）、フルミオキサジン（flumioxazin）、フルオメツロン（fluometuron）、フルオログリコフェンエチル（fluoroglycofen-ethyl）、フルピルスルフロン（flupyrsulfuron）、フルポキサム（flupoxam）、フルレノール（flurenol）、フルリドン（fluridone）、フルロクロリドン（flurochloridone）、フルロキシピル（fluroxypyr）、フルロキシピルのエステル（fluroxypyr-esters）、フルプリミドール（flurprimidol）、フルタモン（flurtamone）、フルチアセットメチル（fluthiacet-methyl）、フォメサフェン（fomesafen）、フォラムスルフロン（foramsulfuron）、フォサミン（fosamine）、グルホシネート（glufosinate）、グルホシネートアンモニウム（glufosinate-ammonium）、グリホサート（glyphosate）、グリホサートアンモニウム（glyphosate-ammonium）、グリホサートイソプロピルアミン（glyphosate-iso-propylammonium）、グリホサートカリウム（glyphosate-potassium）、グリホサートナトリウム（glyphosate-sodium）、グリホサートトリメシウム（glyphosate-trimesium）、ハロウキシフェン（halauxifen）、ハロウキシフェンの塩およびエステル（halauxifen-salts and esters）、ハロサフェン（halosafen）、ハロスルフロン（halosulfuron）、ハロスルフロンメチル（halosulfuron-methyl）、ハロキシホップ（haloxyfop）、ハロキシホップメチル（haloxyfop-methyl）、ヘキサジノン（hexazinone）、イマザメタベンズメチル（imazamethabenz-methyl）、イマザモックス（imazamox）、イマザピク（imazapic）、イマザピル（imazapyr）、イマゼタピル（imazethapyr）、イマザキン（imazaquin）、イマゾスルフロン（imazosulfuron）、インダノファン（indanofan）、インダジフラム（indaziflam）、ヨードスルフロンメチルナトリウム（iodosulfuron-methyl-sodium）、アイオキシニル（ioxynil octanoate）、アイオキシニルの塩およびエステル（ioxynil-salts and esters）、イプフェンカルバゾン（ipfencarbazone）、イソプロチュロン（isoproturon）、イソウロン（isouron）、イソキサベン（isoxaben）、イソキサフルトール（isoxaflutole）、カルブチレート（karbutilate）、ラクトフェン（lactofen）、レナシル（lenacil）、リニュロン（linuron）、マレイン酸ヒドラジド（maleic hydrazide）、MCPA、MCPAの塩およびエステル（MCPA-salts and esters）、MCPB、MCPBの塩およびエステル（MCPB-salts and esters）、メコプロップ（mecoprop、MCPP）、メコプロップの塩およびエステル（mecoprop-salts and esters）、Pメコプロップ（mecoprop-P、MCPP-P）、Pメコプロップの塩およびエステル（mecoprop-P-salts and esters）、メフェナセット（mefenacet）、メフルイジド（mefluidide）、メソスルフロンメチル（mesosulfuron-methyl）、メソトリオン（mesotrione）、メタム（metam）、メタミホップ（metamifop）、メタミトロン（metamitron）、メタザクロール（metazachlor）、メタベンズチアズロン（methabenzthiazuron）、メタゾスルフロン（metazosulfuron）、メチオゾリン（methiozolin）、メチルアジド（methyl azide）、臭化メチル（methyl bromide）、メチルダイムロン（methyl dymron）、ヨウ化メチル（methyl iodide）、メトベンズロン（metobenzuron）、メトラクロール（metolachlor）、Sメトラクロール（metolachlor-S）、メトスラム（metosulam）、メトリブジン（metribuzin）、メトスルフロンメチル（metsulfuron-methyl）、メトクスロン（metoxuron）、モリネート（molinate）、モノリニュロン（monolinuron）、モノスルフロン（monosulfuron）、モノスルフロンメチル（monosulfuron-methyl）、MSMA、ナプロアニリド（naproanilide）、ナプロパミド（napropamide）、ナプタラム（naptalam）、ナプタラムナトリウム（naptalam-sodium）、ネブロン（neburon）、ニコスルフロン（nicosulfuron）、ノルフルラゾン（norflurazon）、OK-701（試験名）、オレイン酸（oleic acid）、オルベンカーブ（orbencarb）、オルソスルファムロン（orthosulfamuron）、オリザリン（oryzalin）、オキサジアルギル（oxadiargyl）、オキサジアゾン（oxadiazon）、オキサスルフロン（oxasulfuron）、オキサジクロメホン（oxaziclomefone）、オキシフルオルフェン（oxyfluorfen）、パラコート（paraquat）、ペラルゴン酸（pelargonicacid）、ペンディメタリン（pendimethalin）、ペノキススラム（penoxsulam）、ペンタノクロール（pentanochlor）、
ペントキサゾン（pentoxazone）、ペトキサミド（pethoxamid）、フェンメディファムエチル（phenmedipham-ethyl）、ピクロラム（picloram）、ピクロラムの塩およびエステル（picloram-salts and esters）、ピコリナフェン（picolinafen）、ピノキサデン（pinoxaden）、ピペロフォス（piperophos）、プレチラクロール（pretilachlor）、プリミスルフロンメチル（primisulfuron-methyl）、プロジアミン（prodiamine）、プロフルアゾール（profluazol）、プロフォキシジム（profoxydim）、プロメトン（prometon）、プロメトリン（prometryn）、プロパクロール（propachlor）、プロパニル（propanil）、プロパキザホップ（propaquizafop）、プロパジン（propazin）、プロファム（propham）、プロピソクロール（propisochlor）、プロポキシカルバゾンナトリウム（propoxycarbazone-sodium）、プロピリスルフロン（propyrisulfuron）、プロピザミド（propyzamide）、プルスルホカーブ（prosulfocarb）、プロスルフロン（prosulfuron）、ピラクロニル（pyraclonil）、ピラフルフェンエチル（pyraflufen-ethyl）、ピラスルホトール（pyrasulfotole）、ピラゾリネート（pyrazolynate）、ピラゾスルフロン（pyrazosulfuron）、ピラゾスルフロンエチル（pyrazosulfuron-ethyl）、ピラゾキシフェン（pyrazoxyfen）、ピリベンゾキシム（pyribenzoxim）、ピリブチカルブ（pyributicarb）、ピリダフォル（pyridafol）、ピリデート（pyridate）、ピリフタリド（pyriftalid）、ピリミノバックメチル（pyriminobac-methyl）、ピリミスルファン（pyrimisulfan）、ピリチオバックナトリウム（pyrithiobac-sodium）、ピロキサスルホン（pyroxasulfone）、ピロキシスラム（pyroxsulam）、キンクロラック（quinclorac）、キンメラック（quinmerac）、キノクラミン（quinoclamine）、キザロホップ（quizalofop）、キザロホップエチル（quizalofop-ethyl）、キザロホップテフリル（quizalofop-tefuryl）、Pキザロホップ（quizalofop-P）、Pキザロホップエチル（quizalofop-P-ethyl）、Pキザロホップテフリル（quizalofop-P-tefuryl）、リムスルフロン（rimsulfuron）、サフルフェナシル（saflufenacil）、セトキシジム（sethoxydim）、シデュロン（siduron）、シマジン（simazine）、シメトリン（simetryn）、SL-261（試験名）、スルコトリオン（sulcotrione）、スルフェントラゾン（sulfentrazone）、スルフォメツロンメチル（sulfometuron-methyl）、スルフォスルフロン（sulfosulfuron）、TCBA（2,3,6-TBA）、TCBAの塩およびエステル（2,3,6-TBA-salts and esters）、TCTP（chlorthal-dimethyl,tetorachlorothiophene）、テブタム（tebutam）、テブティウロン（tebuthiuron）、テフリルトリオン（tefuryltrione）、テンボトリオン（tembotrione）、テプラロキシジム（tepraloxydim）、ターバシル（terbacil）、ターブメトン（terbumeton）、ターブチラジン（terbuthylazine）、ターブトリン（terbutryn）、テトラピオン（tetrapion／flupropanate）、テニルクロール（thenylchlor）、チアザフルロン（thiazafluron）、チアゾピル（thiazopyr）、チジアジミン（thidiazimin）、チジアズロン（thidiazuron）、チエンカルバゾンメチル（thiencarbazone-methyl）、チフェンスルフロンメチル（thifensulfuron-methyl）、トルピラレート（tolpyralate）、トプラメゾン（topramezon）、トラルコキシジム（tralkoxydim）、トリアファモン（triafamone）、トリアレート（triallate）、トリアスルフロン（triasulfuron）、トリアジフラム（triaziflam）、トリベニュロンメチル（tribenuron-methyl）、トリクロピル（triclopyr）、トリクロピルの塩およびエステル（triclopyr-salts and esters）、トリディファン（tridiphane）、トリエタジン（trietazine）、トリフルディモキサジン（trifludimoxadin）、トリフロキシスルフロン（trifloxysulfuron）、トリフルラリン（trifluralin）、トリフルスルフロンメチル（triflusulfuron-methyl）、トリトスルフロン（tritosulfuron）、2,4-PA、2,4-PAの塩およびエステル（2,4-PA-salts and esters）、2,4-DB、2,4-DBの塩およびエステル（2,4-DB-salts and esters）、2,4-D、フロピラウキシフェン（florpyrauxifen）、フロピラウキシフェンベンジル（florpyrauxifen-benzyl）、フルセトスルフロン（flucetosulfuron）、ランコトリオン（lancotrione）、ランコトリオン－ナトリウム塩（lancotrione-sodium）、プロスルホカーブ（prosulfocarb）、チアフェナシル（tiafenacil）等が挙げられる。これらの成分は単独でまたは2種以上混合して使用することができ、混合する場合の比も自由に選択できる。 Preferred herbicides for use in combination with the compounds of the present invention include, for example, acetochlor, acifluorfen, acronifen, alachlor, alloxydim, alloxydim sodium (Alloxydim-sodium), amethrin (ametryn), amicarbazone, amidosulfuron, aminocyclopirachlor, aminocyclopirachlor salts and esters (aminocyclopirachlor-salts and esters), aminopyralid ), Salts and esters of aminopyralid (aminopyralid-salts and esters), amiprophos-methyl, amitrol, anilofos, asuram, atrazine, azafenidin, Azimuth Azimsulfuron, beflubutamid, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bensulide, bensulide bentazone, bentazone sodium (bentazone-sodium), bentazone salts (bentazone-salts), benthiocarb, benzfendizone, benzobicyclon, benzofenap, benzofenap, bialaphos ), Bialaphos-sodium, bicyclopyrone, bifenox, bispyribac, bispyribac-sodium, bromacil, bromobutide, Bromofenoxim, bromoxynil, bromoxynil-salts and esters, butachlor, butafenacil, butamifos, butenachlor, butralin, Of butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone-ethyl, chloromethoxyfen, chloromethoxynil, chloramben, chloramben Chloramben-salts and esters, chloransulam-methyl, chlorflurenol-methyl, chloridazon, chlorimuron-ethyl , Chlorobromuron, chlorotoluron, chloroxuron, chlorphtalim, chlorpropham, chloropropham, chlorsulfuron, chlorthal-dimethyl ), Chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomazone (Clomeprop), clopyralid, clopyralid-salts and esters, CNP, cumyluron, cyanazin, cycloate, cyclopyrimorat e, SW-065 (test name), cyclosulfamuron (cyclosulfamuron), cycloxydim (cycloxydim), cyhalofop-butyl, DAH-500 (test name), dalapon (dalapon), dazomet (dazomet) , Desmedipham, desmetryn, dicamba, dicamba-salts and esters, dichlobenil, diclofop, diclofop-methyl, Dichlorprop, dichlorprop-salts and esters, P dichlorprop-P, P dichlorprop-P-salts and esters, Diclosram, difenzoquat, diflufenican, diflufenzopir (diflufenz) opyr), diflufenzopyr-sodium, dimepiperate, dimethametryn, dimethachlor, dimethenamid, P dimethenamid-p, dimethamine, dimethipin, dimethipin dinitramine, dinoseb, dinoterb, DNOC, diphenamid, diquqt, dithiopyl, diuron, DSMA, dymron, endothal, EPTC, Esprocarb, ethalfluralin, ethametsulfuron-methyl, etofumesate, ettobenzanid, ethoxysulfuron, flazasulfuron, foxasulfuron, foxasulfuron fe noxaprop), fenoxaprop-ethyl, fenoxasulfone, fenquionotrion, fentrazamide, flamrazprop, flazasulfuron, florasulflam, florasulam, Fluazifop, fluazifop-butyl, fluazolate, flucarbazone-sodium, flucetosulfuron, flucloralin, flufenacet, full Flufenpyl-ethyl, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl, flupirsulfurfur (Flupyrsulfuron), flupoxam (flupoxam), flurenol (flurenol), fluridone (fluridone), flurochloridone (flurooxypyr), esters of fluroxypyr (fluroxypyr-esters), flurprimidol (flurprimidol) flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glyphosate, glyphosate ammonium (glyphosate ammonium) glyphosate-ammonium), glyphosate-iso-propylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trime sium), haloxifen, haloxifen-salts and esters, halosafen, halosulfuron, halosulfuron-methyl, halooxyfop, Haloxyfop-methyl, hexaazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazethapyr, imazaquin , Imazosulfuron, indanofan, indaziflam, iodosulfuron-methyl-sodium, ioxynil octanoate, ioxynil-salts and esters, ipfencal Bafen (ipfencarbazone), isoproturon (isoproturon), isouron (isouron), isoxaben (isoxaben), isoxaflutole (isoxaflutole), carbbutate (karbutilate), lactofen (lactofen), renacil (lenacil), linuron (linuron) Maleic hydrazide, MCPA, MCPA salts and esters, MCPB, MCPB salts and esters, MCPB-salts and esters, mecoprop, MCPP, mecoprop salts and esters (Mecoprop-salts and esters), P mecoprop (P, MCPP-P), P mecoprop salts and esters, mefenacet, mefenacet, mefluidide, mesosulfuron methyl ( mesosulfuron-methyl, mesotrione, metam, metamifop, Metrontron, metazachlor, methabenzthiazuron, metazosulfuron, methiozolin, methyl azide, methyl bromide, methyl dymron , Methyl iodide, mettobenzuron, metolachlor, S metolachlor-S, metsuchlor, metribuzin, metsulfuron-methyl, metoxuron metoxuron, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MSMA, naproanilide, napropamide, naptalam, naptalam sodium am-sodium), neburon, nicosulfuron, norflurazon, OK-701 (test name), oleic acid, orbencarb, orthosulfamuron, oryzalin (Oryzalin), oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, Penoxsulam, pentanochlor,
Pentoxazone, pethoxamid, phenmedipham-ethyl, picloram, salts and esters of picloram (picloram-salts and esters), picolinafen, pinoxaden, piperofos ( piperophos, pretilachlor, primisulfuron-methyl, prodiamine, profluazol, prooxydim, prometon, promethrin, propachlor ), Propanil, propaquizafop, propazin, propham, propisochlor, propoxycarbazone-sodium, propyrisulfuron (propyr) isulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazolynate, pyrazosulfuron ( pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxifen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyrinobac-methyl methyl), pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, kinok Lamin (quinoclamine), quizalofop, quizalofop-ethyl, quizalofop-tefuryl, P quizalofop-P, P quizalofop-P-ethyl ), P quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261 (Test name), sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosulfuron, TCBA (2,3,6-TBA), TCBA salt And esters (2,3,6-TBA-salts and esters), TCTP (chlorthal-dimethyl, tetorachlorothiophene), tebutam, tebuthiuron, tefuryltri Tefuryltrione, tembotrione, tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, tetrapion / flupropanate, chlor, thenylchlor (Thiazafluron), thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron-methyl, tolpyralate, topramezon, Tralkoxydim, triafamone, trialate, triasulfuron, triaziflam, tribenuron-methyl, triclop yr), triclopyr-salts and esters, tridiphane, trietazine, trifludimoxadin, trifloxysulfuron, trifluralin, triflu Triflusulfuron-methyl, tritosulfuron, 2,4-PA, 2,4-PA salts and esters (2,4-PA-salts and esters), 2,4-DB, 2 , 4-DB salts and esters, 2,4-D, flopirauxifen, flupirauxifen-benzyl, flucetosulfuron ), Lancotrione, lancotrione-sodium, prosulfocarb, tiafenacil, and the like. These components can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.
　薬害軽減剤としては、例えば、AD-67、ベノキサコル（benoxacor）、クロキントセットメキシル（cloquintocet-mexyl）、シオメトリニル（cyomerinil）、ジクロルミド（dichlormid）、ジシクロノン（dicyclonone）、シプロスルファミド（cyprosulfamide）、ジエトレート（diethorate）、DKA-24、ダイムロン（dymron）、フェンクロラゾールエチル（fenclorazole-ethyl）、フェンクロリム（fenclorim）、ヘキシム（HEXIM）、フルラゾール（flurazole）、フルキソフェニム（fluxofenim）、フリラゾール（furilazole）、イソキサジフェン（isoxadifen）、イソキサジフェンエチル（isoxadifen-ethyl）、MCPA、メコプロップ（mecoprop）、メトカミフェン（metcamifen）、メフェンピル（mefenpyr）、メフェンピルエチル（mefenpyr-ethyl）、メフェンピルジエチル（mefenpyr-diethyl）、メフェネート（mephenate）、MG-191、NA（Naphthalic anhydride）、OM（Octamethylene-diamine）、オキサベトリニル（oxabetrinil）、PPG-1292、R-29148等が挙げられる。これらの成分は単独でまたは2種以上混合して使用することができ、混合する場合の比も自由に選択できる。 Examples of safeners include AD-67, benoxacor, cloquintocet-mexyl, cyomerinil, dichlormid, dicyclonone, cyprosulfamide , Diethorate, DKA-24, dymron, fenclorazole-ethyl, fenclorim, hexim (HEXIM), flurazole, flxofenim, furilazole, Isoxadifen (isoxadifen), isoxadifen-ethyl, MCPA, mecoprop, meetcamifen, mefenpyr, mefenpyr-ethyl, mefenpyr-me diethyl), mephenate, MG-1 91, NA (Naphthalic anhydride), OM (Octamethylene-diamine), oxabetrinil, PPG-1292, R-29148 and the like. These components can be used alone or in admixture of two or more, and the ratio in the case of mixing can also be freely selected.
　以下に本発明の除草剤において、活性成分として用いられる式（１）で表されるケトン若しくはオキシム化合物の合成例、試験例を実施例として具体的に述べることで、本発明を更に詳しく説明するが、本発明はこれらによって限定されるものではない。 In the herbicide of the present invention, the present invention will be described in more detail by specifically describing, as examples, synthesis examples and test examples of ketones or oxime compounds represented by the formula (1) used as an active ingredient. However, the present invention is not limited by these.
　［合成例］
　以下の合成例に記載した中圧分取液体クロマトグラフィーは、山善社製、中圧分取装置；ＹＦＬＣ－Ｗｐｒｅｐ（流速１８ｍｌ／ｍｉｎ、シリカゲル４０μｍのカラム）を使用した。
　また、実施例のプロトン核磁気共鳴ケミカルシフト値は、基準物質としてＭｅ４Ｓｉ（テトラメチルシラン）を用い、３００ＭＨｚにて測定した。また測定に使用した溶媒を以下の合成例中に記載する。また、実施例のプロトン核磁気共鳴ケミカルシフト値における記号は、下記の意味を表す。
ｓ：シングレット、ｂｒｓ：ブロードシングレット、ｄ：ダブレット、ｔ：トリプレット、ｑ：カルテット、ｍ：マルチプレット [Synthesis example]
The medium pressure preparative liquid chromatography described in the following synthesis examples used an intermediate pressure preparative device manufactured by Yamazen Co., Ltd .; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).
Moreover, the proton nuclear magnetic resonance chemical shift value of the Example was measured at 300 MHz using Me 4 Si (tetramethylsilane) as a reference material. Moreover, the solvent used for the measurement is described in the following synthesis examples. Moreover, the symbol in the proton nuclear magnetic resonance chemical shift value of an Example represents the following meaning.
s: singlet, brs: broad singlet, d: doublet, t: triplet, q: quartet, m: multiplet
　合成例１：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造（化合物Ｎｏ．１－００２）
　工程１：メチル　２－｛３－（５－ブロモ－２－メトキシフェニル）－４－ヒドロキシ－２－オキソシクロペンタ－３－エン－１－イル｝－３－オキソブタノエートの製造
　アセト酢酸メチル１．４５ｇ及びアセトニトリル６０ｍｌの混合溶液に、炭酸カリウム１７．７ｇを添加し、室温にて３０分間撹拌した。この混合溶液に、別途調整した２－（５－ブロモ－２－メトキシフェニル）シクロペンタ－４－エン－１，３－ジオン３ｇ及びアセトニトリル６０ｍｌの混合溶液を添加し、室温にて１５分間撹拌した。反応終了後、該反応溶液の溶媒を留去した後、１ｍｏｌ／Ｌ塩酸６０ｍｌを添加し、酢酸エチル６０ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン：酢酸エチル［３：１～１：１（体積比、以下同じである。）のグラジエント］にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物４．３ｇを白色固体として得た。
融点；１２２－１２５℃ Synthesis Example 1: 2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-ene- Production of 1-one (Compound No. 1-002)
Step 1: Preparation of methyl 2- {3- (5-bromo-2-methoxyphenyl) -4-hydroxy-2-oxocyclopent-3-en-1-yl} -3-oxobutanoate Methyl acetoacetate To a mixed solution of 1.45 g and 60 ml of acetonitrile, 17.7 g of potassium carbonate was added and stirred at room temperature for 30 minutes. To this mixed solution, a separately prepared mixed solution of 3 g of 2- (5-bromo-2-methoxyphenyl) cyclopent-4-ene-1,3-dione and 60 ml of acetonitrile was added and stirred at room temperature for 15 minutes. After completion of the reaction, the solvent of the reaction solution was distilled off, 60 ml of 1 mol / L hydrochloric acid was added, and the mixture was extracted with 60 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane: ethyl acetate [gradient of 3: 1 to 1: 1 (volume ratio, the same shall apply hereinafter)]. 4.3 g of product was obtained as a white solid.
Melting point: 122-125 ° C
　工程２：２－（５－ブロモ－２－メトキシフェニル）－３－ヒドロキシ－５－（２－オキソプロピル）シクロペンタ－２－エン－１－オンの製造
　メチル　２－｛３－（５－ブロモ－２－メトキシフェニル）－４－ヒドロキシ－２－オキソシクロペンタ－３－エン－１－イル｝－３－オキソブタノエート０．３ｇ、メタノール２ｍｌ及び水２ｍｌの混合溶液に、水酸化カリウム０．１５ｇを添加し、室温にて５時間撹拌した。反応終了後、該反応溶液の溶媒を減圧下にて留去した。得られた残留物に水５ｍｌを添加し、次いで濃塩酸を添加してｐＨ１とした。該反応混合物を酢酸エチル７ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で脱水・乾燥し、減圧下にて溶媒を留去することにより、目的物０．２５ｇを薄黄色固体として得た。
融点；１６０－１６４℃ Step 2: Preparation of 2- (5-bromo-2-methoxyphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one Methyl 2- {3- (5-Bromo- 2-methoxyphenyl) -4-hydroxy-2-oxocyclopent-3-en-1-yl} -3-oxobutanoate 0.3 g, 2 ml of methanol and 2 ml of water were mixed with 0. 15 g was added and stirred at room temperature for 5 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure. 5 ml of water was added to the obtained residue, and then concentrated hydrochloric acid was added to adjust the pH to 1. The reaction mixture was extracted with 7 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.25 g of the desired product as a pale yellow solid.
Melting point: 160-164 ° C
　工程３：２－（５－ブロモ－２－メトキシフェニル）－３－ヒドロキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　２－（５－ブロモ－２－メトキシフェニル）－３－ヒドロキシ－５－（２－オキソプロピル）シクロペンタ－２－エン－１－オン０．２５ｇ、メタノール４ｍｌ及び水１ｍｌの混合溶媒に、Ｏ－メチルヒドロキシルアミン　塩酸塩９４ｍｇを添加し、室温にて２時間撹拌した。反応終了後、該反応溶液の溶媒を減圧下にて留去した。得られた残留物に水７ｍｌを添加した後、酢酸エチル７ｍｌにて抽出した。得られた有機層を飽和食塩水次いで無水硫酸ナトリウムの順で脱水・乾燥し、減圧下にて溶媒を留去することにより、目的物０．２４ｇを白色固体として得た。
融点；１４９－１５３℃ Step 3: Preparation of 2- (5-bromo-2-methoxyphenyl) -3-hydroxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 2- (5-bromo-2 To a mixed solvent of -methoxyphenyl) -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one 0.25 g, methanol 4 ml and water 1 ml, 94 mg of O-methylhydroxylamine hydrochloride was added And stirred at room temperature for 2 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure. After adding 7 ml of water to the obtained residue, extraction was performed with 7 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.24 g of the desired product as a white solid.
Melting point: 149-153 ° C
　工程４：２－（５－ブロモ－２－メトキシフェニル）－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　２－（５－ブロモ－２－メトキシフェニル）－３－ヒドロキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン３．５ｇ及びＮ，Ｎ－ジメチルホルムアミド９５ｍｌの混合溶液に、炭酸カリウム２ｇ次いでジメチル硫酸１．８ｇを順次添加し、室温にて４５分間撹拌した。反応終了後、該反応溶液に水１００ｍｌを添加し、酢酸エチル１００ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（１５：１～１：３のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物３．２ｇを黄色油状物として得た。
1H NMR(CDCl3)；δ7.44-7.33 (m, 1H), 7.27-7.21 (m, 1H), 6.86-6.72 (m, 1H), 3.85 and 3.84 and 3.67 and 3.66 (s, 6H), 3.76 and 3.75 (s, 3H), 3.23-3.10 and 2.98-2.49 (m, 4H), 2.43-2.20 (m, 1H), 1.92 and 1.87 (s, 3H). Step 4: Preparation of 2- (5-bromo-2-methoxyphenyl) -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 2- (5-bromo-2 -Methoxyphenyl) -3-hydroxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one in a mixed solution of 3.5 g and N, N-dimethylformamide 95 ml, 2 g of potassium carbonate and then dimethyl Sulfuric acid (1.8 g) was sequentially added, and the mixture was stirred at room temperature for 45 minutes. After completion of the reaction, 100 ml of water was added to the reaction solution and extracted with 100 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 15: 1 to 1: 3) to obtain 3.2 g of the objective product as a yellow oil. It was.
1 H NMR (CDCl 3 ); δ 7.44-7.33 (m, 1H), 7.27-7.21 (m, 1H), 6.86-6.72 (m, 1H), 3.85 and 3.84 and 3.67 and 3.66 (s, 6H), 3.76 and 3.75 (s, 3H), 3.23-3.10 and 2.98-2.49 (m, 4H), 2.43-2.20 (m, 1H), 1.92 and 1.87 (s, 3H).
　工程５：３－メトキシ－２－｛２－メトキシ－５－（４，４，５，５－テトラメチル－１，３，２－ジオキサボロラン－２－イル）フェニル｝－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　２－（５－ブロモ－２－メトキシフェニル）－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン１ｇ、ビス（ピナコラト）ジボロン１ｇ、１，４－ジオキサン５ｍｌの混合溶液に、酢酸カリウム０．３８ｇ、２－ジシクロヘキシルホスフィノ－２’，６’－ジメトキシビフェニル０．２１ｇ、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド　ジクロロメタン付加物０．２４ｇを順次添加した。添加終了後、該反応容器中を窒素ガスで置換した後、８５℃にて３時間撹拌した。反応終了後、該反応混合物に水３ｍｌを添加した後、酢酸エチル２０ｍｌで抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（８：１～１：３のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物１．１ｇを橙色油状物として得た。
1H NMR(CDCl3)；δ7.83-7.70 (m, 1H), 7.60-7.50 (m, 1H), 6.98-6.85 (m, 1H), 3.94-3.60 (m, 9H), 2.97-2.43 (m, 3H), 2.31-2.14 (m, 2H), 1.99-1.83 (m, 3H), 1.31 and 1.24 (s, 12H). Step 5: 3-methoxy-2- {2-methoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl} -5- {2- (methoxy Preparation of imino) propyl} cyclopent-2-en-1-one 2- (5-bromo-2-methoxyphenyl) -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-ene-1 -To a mixed solution of 1 g of ONE, 1 g of bis (pinacolato) diboron and 5 ml of 1,4-dioxane, 0.38 g of potassium acetate, 0.21 g of 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl, [1,1 '-Bis (diphenylphosphino) ferrocene] palladium (II) dichloride 0.24 g of dichloromethane adduct was sequentially added. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 85 ° C. for 3 hours. After completion of the reaction, 3 ml of water was added to the reaction mixture, followed by extraction with 20 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 8: 1 to 1: 3) to obtain 1.1 g of the objective product as an orange oil. It was.
1 H NMR (CDCl 3 ); δ7.83-7.70 (m, 1H), 7.60-7.50 (m, 1H), 6.98-6.85 (m, 1H), 3.94-3.60 (m, 9H), 2.97-2.43 ( m, 3H), 2.31-2.14 (m, 2H), 1.99-1.83 (m, 3H), 1.31 and 1.24 (s, 12H).
　工程６：２－（５－ヒドロキシ－２－メトキシフェニル）－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　３－メトキシ－２－｛２－メトキシ－５－（４，４，５，５－テトラメチル－１，３，２－ジオキサボロラン－２－イル）フェニル｝－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン０．９ｇ及びテトラヒドロフラン９ｍｌの混合溶液を０℃に冷却して、水酸化ナトリウム０．２５ｇ、３０質量％過酸化水素水０．６ｍｌを順次添加した。添加終了後、室温にて４０分間撹拌した。反応終了後、該反応溶液に、水１０ｍｌを添加して、酢酸エチル１０ｍｌにて抽出した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（３：１～１：３のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．１９ｇを黄色油状物として得た。
1H NMR(CDCl3)；δ6.80-6.50 (m, 3H), 3.95-3.60 (m, 9H), 3.22-2.20 (m, 5H), 1.94 and 1.92 and 1.87 and 1.86 (s, 3H) (OHのシグナルは観測されなかった). Step 6: Preparation of 2- (5-hydroxy-2-methoxyphenyl) -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 3-methoxy-2- {2 -Methoxy-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl} -5- {2- (methoxyimino) propyl} cyclopent-2-ene-1 -A mixed solution of 0.9 g of ON and 9 ml of tetrahydrofuran was cooled to 0 ° C, and 0.25 g of sodium hydroxide and 0.6 ml of 30% by mass hydrogen peroxide were sequentially added. After completion of the addition, the mixture was stirred at room temperature for 40 minutes. After completion of the reaction, 10 ml of water was added to the reaction solution and extracted with 10 ml of ethyl acetate. The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 3: 1 to 1: 3) to obtain 0.19 g of the objective product as a yellow oil. It was.
1 H NMR (CDCl 3 ); δ 6.80-6.50 (m, 3H), 3.95-3.60 (m, 9H), 3.22-2.20 (m, 5H), 1.94 and 1.92 and 1.87 and 1.86 (s, 3H) ( No OH signal was observed).
　工程７：２－[５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル]－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　２－（５－ヒドロキシ－２－メトキシフェニル）－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン０．１９ｇ及びアセトニトリル３ｍｌの混合溶液に、炭酸カリウム０．２５ｇ及び２，６－ジクロロキノキサリン０．１３ｇを添加した。添加終了後、８０℃にて２時間撹拌した。反応終了後、該反応溶液を室温まで放冷した後、水７ｍｌを添加し、酢酸エチル７ｍｌで抽出した。得られた残留物をｎ－ヘキサン－酢酸エチル（８：１～１：２のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．２５ｇを黄色油状物として得た。
1H NMR(CDCl3)；δ8.71-8.67 (m, 1H), 8.09-8.02 (m, 1H), 7.73-7.57 (m, 2H), 7.26-7.18 (m, 1H), 7.10-7.04 (m, 1H), 7.00-6.92 (m, 1H), 3.93-3.79 (m, 9H), 3.22-3.11 and 2.98-2.20 (m, 5H), 1.93 and 1.92 and 1.86 (s, 3H). Step 7: 2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-ene-1 Production of 2-one A mixed solution of 0.19 g of 2- (5-hydroxy-2-methoxyphenyl) -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one and 3 ml of acetonitrile 0.25 g of potassium carbonate and 0.13 g of 2,6-dichloroquinoxaline were added. After completion of the addition, the mixture was stirred at 80 ° C. for 2 hours. After completion of the reaction, the reaction solution was allowed to cool to room temperature, 7 ml of water was added, and the mixture was extracted with 7 ml of ethyl acetate. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 8: 1 to 1: 2) to obtain 0.25 g of the desired product as a yellow oil. It was.
1 H NMR (CDCl 3 ); δ8.71-8.67 (m, 1H), 8.09-8.02 (m, 1H), 7.73-7.57 (m, 2H), 7.26-7.18 (m, 1H), 7.10-7.04 ( m, 1H), 7.00-6.92 (m, 1H), 3.93-3.79 (m, 9H), 3.22-3.11 and 2.98-2.20 (m, 5H), 1.93 and 1.92 and 1.86 (s, 3H).
　合成例２：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－（２－オキソプロピル）シクロペンタ－２－エン－１－オンの製造（化合物No.2-001）
　２－[５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル]－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン０．１２ｇ及びアセトン２ｍｌの混合溶液に、２Ｍ塩酸水溶液１ｍｌを添加した。添加終了後、該反応混合物を６０℃にて４０分間撹拌した。反応終了後、該反応混合物に酢酸エチル５ｍｌを添加し、有機層を取り出した。得られた有機層を水洗した後、無水硫酸ナトリウムにて脱水・乾燥後、減圧下にて溶媒を留去し、目的物６５ｍｇを黄白色固体として得た。
融点；１６１－１６５℃ Synthesis Example 2: 2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one (Compound No.2-001)
2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 0 To a mixed solution of .12 g and 2 ml of acetone, 1 ml of 2M hydrochloric acid aqueous solution was added. After the addition was complete, the reaction mixture was stirred at 60 ° C. for 40 minutes. After completion of the reaction, 5 ml of ethyl acetate was added to the reaction mixture, and the organic layer was taken out. The obtained organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 65 mg of the objective product as a yellowish white solid.
Melting point: 161-165 ° C
　合成例３：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造（化合物No.1-001）
　２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－（２－オキソプロピル）シクロペンタ－２－エン－１－オン５０ｍｇ、メタノール１．５ｍｌ及び水０．５ｍｌの混合溶液に、Ｏ－メチルヒドロキシルアミン　塩酸塩１４ｍｇを添加した。添加終了後、該反応混合物を室温にて２時間撹拌した。反応終了後、該反応混合物から減圧下にて溶媒を留去した。得られた残留物に酢酸エチル５ｍｌを添加した後、水洗した。得られた有機層を、飽和食塩水次いで無水硫酸ナトリウムの順で脱水・乾燥し、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（１：１～１：２のグラジエント）にて溶出するシリカゲルクロマトグラフィーにて精製し、目的物１９ｍｇを黄色油状物として得た。
1H NMR(CDCl3)；δ10.52 and 9.24 (brs, 1H), 8.72-8.67 (m, 1H), 8.08-8.03 (m, 1H), 7.87-7.82 and 7.50-7.46 (m, 1H), 7.77-7.69 (m, 1H), 7.62-7.57 (m, 1H), 7.25-7.18 (m, 1H), 7.13-7.01 (m, 1H), 4.00 and 3.92 (s, 3H), 3.88 and 3.82 (s, 3H), 2.98-2.68 (m, 3H), 2.58-2.48 (m, 1H), 2.38-2.18 (m, 1H), 1.98-1.82 (m, 3H). Synthesis Example 3: 2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- {2- (methoxyimino) propyl} cyclopent-2-ene- Production of 1-one (Compound No.1-001)
2- [5-{(6-chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one 50 mg, methanol 1 To a mixed solution of 0.5 ml and 0.5 ml of water, 14 mg of O-methylhydroxylamine hydrochloride was added. After the addition was complete, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. After adding 5 ml of ethyl acetate to the obtained residue, it was washed with water. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography eluting with n-hexane-ethyl acetate (1: 1 to 1: 2 gradient) to obtain 19 mg of the objective product as a yellow oil.
1 H NMR (CDCl 3 ); δ 10.52 and 9.24 (brs, 1H), 8.72-8.67 (m, 1H), 8.08-8.03 (m, 1H), 7.87-7.82 and 7.50-7.46 (m, 1H), 7.77-7.69 (m, 1H), 7.62-7.57 (m, 1H), 7.25-7.18 (m, 1H), 7.13-7.01 (m, 1H), 4.00 and 3.92 (s, 3H), 3.88 and 3.82 (s , 3H), 2.98-2.68 (m, 3H), 2.58-2.48 (m, 1H), 2.38-2.18 (m, 1H), 1.98-1.82 (m, 3H).
　合成例４：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－４－｛２－（メトキシイミノ）プロピル｝－３－オキソシクロペンタ－１－エン－１－イル　メチル　カーボネートの製造（化合物No.1-017）
　２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン０．１５ｇ及びジクロロメタン３ｍｌの混合溶液に、トリエチルアミン０．１ｇ、クロロギ酸メチル４６ｍｇを順次添加し、室温にて３０分間撹拌した。反応終了後、該反応溶液に水５ｍｌを添加し、ジクロロメタン１０ｍｌにて抽出した。得られた有機層を飽和食塩水次いで無水硫酸ナトリウムの順で脱水・乾燥し、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン：酢酸エチル（３：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．１３ｇを白色固体として得た。
融点；４５－５０℃ Synthesis Example 4: 2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -4- {2- (methoxyimino) propyl} -3-oxocyclopent-1-ene Production of -1-yl methyl carbonate (Compound No. 1-017)
2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 0 0.1 g of triethylamine and 46 mg of methyl chloroformate were sequentially added to a mixed solution of .15 g and 3 ml of dichloromethane, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, 5 ml of water was added to the reaction solution and extracted with 10 ml of dichloromethane. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane: ethyl acetate (gradient 3: 1 to 1: 1) to obtain 0.13 g of the objective product as a white solid. .
Melting point: 45-50 ° C
　合成例５：２－［５－｛（６－クロロキノキサリン－２－イル）チオ｝－２－メトキシフェニル］－３－エトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造（化合物No.1-123）
　工程１：２－エチルへキシル　３－［｛４－メトキシ－３－（２－メトキシ－４－｛２－（メトキシイミノ）プロピル｝－５－オキソシクロペンタ－１－エン－１－イル）フェニル｝チオ］プロパノエートの製造
　２－（５－ブロモ－２－メトキシフェニル）－３－メトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン２００ｍｇ及び１，４－ジオキサン５ｍｌの混合溶液に、Ｎ，Ｎ－ジイソプロピルエチルアミン０．２ｇ、４，５－ビス（ジフェニルホスフィノ）－９，９－ジメチルキサンテン３０ｍｇ、３－メルカプトプロピオン酸２－エチルヘキシル１３０ｍｇ、トリス（ジベンジリデンアセトン）ジパラジウム２４ｍｇを順次添加した。添加終了後、該反応容器中を窒素ガスで置換した後、１００℃にて２時間撹拌した。反応終了後、該反応溶液中の不溶物をセライトろ過にて取り除いた後、ろ液の溶媒を減圧下にて留去した。得られた残留物をｎ－ヘキサン：酢酸エチル（３：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．２５ｇを黄色アモルファスとして得た。
1H NMR(CDCl3)；δ7.42-7.17 (m, 2H), 6.92-6.80 (m, 1H), 4.08-3.95 (m, 2H), 3.90-3.60 (m, 9H), 3.25-2.15 (m, 10H), 1.95-1.85 (m, 3H), 1.63-1.20 (m, 8H), 0.98-0.83 (m, 6H). Synthesis Example 5: 2- [5-{(6-chloroquinoxalin-2-yl) thio} -2-methoxyphenyl] -3-ethoxy-5- {2- (methoxyimino) propyl} cyclopent-2-ene- Production of 1-one (Compound No. 1-123)
Step 1: 2-ethylhexyl 3-[{4-methoxy-3- (2-methoxy-4- {2- (methoxyimino) propyl} -5-oxocyclopent-1-en-1-yl) phenyl } Thio] propanoate 2- (5-Bromo-2-methoxyphenyl) -3-methoxy-5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 200 mg and 1,4-dioxane In a 5 ml mixed solution, 0.2 g of N, N-diisopropylethylamine, 30 mg of 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene, 130 mg of 2-ethylhexyl 3-mercaptopropionate, tris (dibenzylideneacetone) ) 24 mg of dipalladium was added sequentially. After completion of the addition, the inside of the reaction vessel was replaced with nitrogen gas, followed by stirring at 100 ° C. for 2 hours. After completion of the reaction, insoluble matters in the reaction solution were removed by Celite filtration, and then the solvent of the filtrate was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane: ethyl acetate (gradient 3: 1 to 1: 1) to obtain 0.25 g of the desired product as a yellow amorphous. .
1 H NMR (CDCl 3 ); δ 7.42-7.17 (m, 2H), 6.92-6.80 (m, 1H), 4.08-3.95 (m, 2H), 3.90-3.60 (m, 9H), 3.25-2.15 ( m, 10H), 1.95-1.85 (m, 3H), 1.63-1.20 (m, 8H), 0.98-0.83 (m, 6H).
　工程２：３－エトキシ－２－（５‐メルカプト－２－メトキシフェニル）－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　２－エチルへキシル　３－［｛４－メトキシ－３－（２－メトキシ－４－｛２－（メトキシイミノ）プロピル｝－５－オキソシクロペンタ－１－エン－１－イル）フェニル｝チオ］プロパノエート０．２ｇ及びエタノール５ｍｌの混合溶液に、ナトリウムエトキシド０．４２ｇを添加し、室温にて２時間撹拌した。反応終了後、該反応溶液に１ｍｏｌ／Ｌ塩酸水溶液を添加してｐＨ３とした後、酢酸エチル５ｍｌにて抽出した。得られた有機層を飽和食塩水次いで無水硫酸ナトリウムの順で脱水・乾燥し、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン：酢酸エチル（１０：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物６３ｍｇを薄黄色油状物として得た。
1H NMR(CDCl3)；δ7.50-7.05 (m, 2H), 6.95-6.75 (m, 1H), 4.30-4.05 (m, 2H), 4.03-3.64 (m, 6H), 3.62-2.19 (m, 6H), 2.00-1.85 (m, 3H), 1.45-1.15 (m, 3H). Step 2: Preparation of 3-ethoxy-2- (5-mercapto-2-methoxyphenyl) -5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 2-ethylhexyl 3- [ Of 0.2 g of {4-methoxy-3- (2-methoxy-4- {2- (methoxyimino) propyl} -5-oxocyclopent-1-en-1-yl) phenyl} thio] propanoate and 5 ml of ethanol To the mixed solution, 0.42 g of sodium ethoxide was added and stirred at room temperature for 2 hours. After completion of the reaction, 1 mol / L hydrochloric acid aqueous solution was added to the reaction solution to adjust the pH to 3, followed by extraction with 5 ml of ethyl acetate. The obtained organic layer was dehydrated and dried in the order of saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane: ethyl acetate (gradient of 10: 1 to 1: 1) to obtain 63 mg of the desired product as a pale yellow oil. .
1 H NMR (CDCl 3 ); δ 7.50-7.05 (m, 2H), 6.95-6.75 (m, 1H), 4.30-4.05 (m, 2H), 4.03-3.64 (m, 6H), 3.62-2.19 ( m, 6H), 2.00-1.85 (m, 3H), 1.45-1.15 (m, 3H).
　工程３：２－［５－｛（６－クロロキノキサリン－２－イル）チオ｝－２－メトキシフェニル］－３－エトキシ－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造
　３－エトキシ－２－（５‐メルカプト－２－メトキシフェニル）－５－｛２－（メトキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン６３ｍｇ及びＮ，Ｎ－ジメチルホルムアミド３ｍｌの混合溶液に、炭酸カリウム７８ｍｇ、２，６－ジクロロキノキサリン４５ｍｇを順次添加し、室温にて１時間撹拌した。反応終了後、該反応溶液に水５ｍｌを添加し、酢酸エチル１０ｍｌにて２回抽出した。得られた有機層を水洗した後、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（５：１～１：２のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物８５ｍｇを黄色油状物として得た。
1H NMR(CDCl3)；δ8.50-8.38 (m, 1H), 8.00-7.90 (m, 1H), 7.85-7.38 (m, 4H), 7.05-6.90 (m, 1H), 4.22-4.05 (m, 2H), 3.90-3.70 (m, 6H), 3.25-2.15 (m, 5H), 1.95-1.80 (m, 3H), 1.35-1.18 (m, 3H). Step 3: 2- [5-{(6-Chloroquinoxalin-2-yl) thio} -2-methoxyphenyl] -3-ethoxy-5- {2- (methoxyimino) propyl} cyclopent-2-ene-1 Preparation of 3-one 3-Ethoxy-2- (5-mercapto-2-methoxyphenyl) -5- {2- (methoxyimino) propyl} cyclopent-2-en-1-one 63 mg and N, N-dimethylformamide 3 ml To the mixed solution, 78 mg of potassium carbonate and 45 mg of 2,6-dichloroquinoxaline were sequentially added, followed by stirring at room temperature for 1 hour. After completion of the reaction, 5 ml of water was added to the reaction solution, and extracted twice with 10 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (gradient 5: 1 to 1: 2) to obtain 85 mg of the desired product as a yellow oil.
1 H NMR (CDCl 3 ); δ 8.50-8.38 (m, 1H), 8.00-7.90 (m, 1H), 7.85-7.38 (m, 4H), 7.05-6.90 (m, 1H), 4.22-4.05 ( m, 2H), 3.90-3.70 (m, 6H), 3.25-2.15 (m, 5H), 1.95-1.80 (m, 3H), 1.35-1.18 (m, 3H).
　合成例６：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－｛２－（ヒドロキシイミノ）プロピル｝シクロペンタ－２－エン－１－オンの製造（化合物No.4-005）
　２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－（２－オキソプロピル）シクロペンタ－２－エン－１－オン２ｇ及びヒドロキシルアミン　塩酸塩０．３５ｇを合成例３と同様の方法を用いて反応させることにより、目的物１．４４ｇを黄色粘性物として得た。
融点；２０３－２０５℃ Synthesis Example 6: 2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- {2- (hydroxyimino) propyl} cyclopent-2-ene- Production of 1-one (Compound No. 4-005)
2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- (2-oxopropyl) cyclopent-2-en-1-one 2 g and hydroxylamine By reacting 0.35 g of hydrochloride using the same method as in Synthesis Example 3, 1.44 g of the desired product was obtained as a yellow viscous product.
Melting point: 203-205 ° C
　合成例７：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－４－｛２－（ヒドロキシイミノ）プロピル｝－３－オキソシクロペンタ－１－エン－１－イル　ジメチルカーバメートの製造（化合物No.4-023）
　２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－３－ヒドロキシ－５－｛２－（ヒドロキシイミノ）プロピル｝シクロペンタ－２－エン－１－オン０．３ｇ及びＮ，Ｎ－ジメチルホルムアミド７ｍｌの混合溶液に、炭酸カリウム０．１４ｇ、ジメチルカルバモイルクロリド８６ｍｇを順次添加し、室温にて３０分間撹拌した。反応終了後、該反応溶液に水１０ｍｌを添加し、酢酸エチル１０ｍｌにて抽出した。得られた有機層を水洗した後、飽和食塩水次いで無水硫酸ナトリウムで脱水・乾燥後、減圧下にて溶媒を留去した。得られた残留物をｎ－ヘキサン－酢酸エチル（４：１～１：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物０．１６ｇを無色油状物として得た。
1H NMR(CDCl3)；δ8.66 (s, 1H), 8.08-7.98 (m, 1H), 7.74-7.67 (m, 1H), 7.63-7.54 (m, 1H), 7.28-7.10 (m, 2H), 7.01-6.92 (m, 1H), 3.81 (s, 3H), 3.40-2.23 (m, 11H), 1.95-1.85 (m, 3H) (OHに相当するシグナルは観測されなかった。). Synthesis Example 7 2- [5-{(6-chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -4- {2- (hydroxyimino) propyl} -3-oxocyclopent-1-ene -1-yl Production of dimethyl carbamate (Compound No. 4-023)
2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -3-hydroxy-5- {2- (hydroxyimino) propyl} cyclopent-2-en-1-one 0 0.14 g of potassium carbonate and 86 mg of dimethylcarbamoyl chloride were sequentially added to a mixed solution of .3 g and 7 ml of N, N-dimethylformamide, followed by stirring at room temperature for 30 minutes. After completion of the reaction, 10 ml of water was added to the reaction solution and extracted with 10 ml of ethyl acetate. The obtained organic layer was washed with water, dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (4: 1 to 1: 1 gradient) to obtain 0.16 g of the objective product as a colorless oil. It was.
1 H NMR (CDCl 3 ); δ 8.66 (s, 1H), 8.08-7.98 (m, 1H), 7.74-7.67 (m, 1H), 7.63-7.54 (m, 1H), 7.28-7.10 (m, 2H), 7.01-6.92 (m, 1H), 3.81 (s, 3H), 3.40-2.23 (m, 11H), 1.95-1.85 (m, 3H) (No signal corresponding to OH was observed).
　合成例８：２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－４－（２－［｛（エチルカルバモイル）オキシ｝イミノ］プロピル）－３－オキソシクロペンタ－１－エン－１－イル　ジメチルカーバメートの製造（化合物No.4-024）
　２－［５－｛（６－クロロキノキサリン－２－イル）オキシ｝－２－メトキシフェニル］－４－｛２－（ヒドロキシイミノ）プロピル｝－３－オキソシクロペンタ－１－エン－１－イル　ジメチルカーバメート７４ｍｇ及びジクロロメタン２ｍｌの混合溶液に、トリエチルアミン２１ｍｇ、イソシアン酸エチル１５ｍｇを添加し、室温にて５５時間撹拌した。反応終了後、該反応溶液の溶媒を、減圧下にて留去した。得られた残留物を、ｎ－ヘキサン－酢酸エチル（４：１～０：１のグラジエント）にて溶出する中圧分取液体クロマトグラフィーにて精製し、目的物５８ｍｇを無色油状物として得た。
1H NMR(CDCl3)；δ8.67 (s, 1H), 8.08-8.02 (m, 1H), 7.74-7.55 (m, 2H), 7.31-6.94 (m, 3H), 6.24-6.11 (m, 1H), 3.82 (s, 3H), 3.37-2.46 (m, 13H), 2.10-2.02 (m, 3H), 1.20-1.06 (m, 3H). Synthesis Example 8 2- [5-{(6-chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -4- (2-[{(ethylcarbamoyl) oxy} imino] propyl) -3-oxo Production of cyclopent-1-en-1-yl dimethylcarbamate (Compound No. 4-024)
2- [5-{(6-Chloroquinoxalin-2-yl) oxy} -2-methoxyphenyl] -4- {2- (hydroxyimino) propyl} -3-oxocyclopent-1-en-1-yl 21 mg of triethylamine and 15 mg of ethyl isocyanate were added to a mixed solution of 74 mg of dimethyl carbamate and 2 ml of dichloromethane, and the mixture was stirred at room temperature for 55 hours. After completion of the reaction, the solvent of the reaction solution was distilled off under reduced pressure. The obtained residue was purified by medium pressure preparative liquid chromatography eluting with n-hexane-ethyl acetate (4: 1 to 0: 1 gradient) to obtain 58 mg of the objective product as a colorless oil. .
1 H NMR (CDCl 3 ); δ 8.67 (s, 1H), 8.08-8.02 (m, 1H), 7.74-7.55 (m, 2H), 7.31-6.94 (m, 3H), 6.24-6.11 (m, 1H), 3.82 (s, 3H), 3.37-2.46 (m, 13H), 2.10-2.02 (m, 3H), 1.20-1.06 (m, 3H).
　参考例１：２－（５－ブロモ－２－メトキシフェニル）シクロペンタ－４－エン１，３－ジオンの製造
　工程１：（５－ブロモ－２－メトキシフェニル）（フラン－２－イル）メタノールの製造
　フラン３６．６ｇ及び５－ブロモ－２－メトキシベンズアルデヒド１０５ｇを、国際公開第２０１６／０９８８９９号記載の方法で反応させることにより、目的物１０５ｇを黄色油状物として得た。
1H NMR(CDCl3)；δ7.52-7.41 (m, 1H), 7.40-7.26 (m, 2H), 6.77 (d, J=8.8Hz, 1H), 6.31-6.29 (m, 1H), 6.15-6.09 (m, 1H), 6.04-6.01 (m, 1H), 3.79 (s, 1H), 2.98 (brs, 1H). Reference Example 1: Production of 2- (5-bromo-2-methoxyphenyl) cyclopent-4-ene 1,3-dione Step 1: (5-Bromo-2-methoxyphenyl) (furan-2-yl) methanol Production By reacting 36.6 g of furan and 105 g of 5-bromo-2-methoxybenzaldehyde by the method described in WO2016 / 098899, 105 g of the desired product was obtained as a yellow oil.
1 H NMR (CDCl 3 ); δ7.52-7.41 (m, 1H), 7.40-7.26 (m, 2H), 6.77 (d, J = 8.8Hz, 1H), 6.31-6.29 (m, 1H), 6.15 -6.09 (m, 1H), 6.04-6.01 (m, 1H), 3.79 (s, 1H), 2.98 (brs, 1H).
　同様の方法を用いて以下の化合物を製造した。
（５－ブロモ－２－フルオロフェニル）（フラン－２－イル）メタノール；
1H NMR(CDCl3)；δ7.80-7.70 (m, 1H), 7.45-7.35 (m, 2H), 7.00-6.90 (m, 1H), 6.35-6.00 (m, 3H), 2.75-2.65 (m, 1H).
（５－ブロモ－２－エトキシフェニル）（フラン－２－イル）メタノール；
1H NMR(CDCl3)；δ7.60-7.30 (m, 3H), 6.80-6.70 (m, 1H), 6.40-6.30 (m, 1H), 6.20-5.90 (m, 2H), 4.20-3.90 (m, 2H), 3.15-2.85 (m, 1H), 1.40-1.30 (m, 3H).
（５－ブロモ－２－メチルフェニル）（フラン－２－イル）メタノール；
1H NMR(CDCl3)；δ7.80-7.70 (m, 1H), 7.45-7.20 (m, 2H), 7.10-6.95 (m, 1H), 6.40-6.25 (m, 1H), 6.10-5.90 (m, 2H), 2.45-2.35 (m, 1H), 2.19 (m, 3H). The following compounds were prepared using similar methods.
(5-bromo-2-fluorophenyl) (furan-2-yl) methanol;
1 H NMR (CDCl 3 ); δ 7.80-7.70 (m, 1H), 7.45-7.35 (m, 2H), 7.00-6.90 (m, 1H), 6.35-6.00 (m, 3H), 2.75-2.65 ( m, 1H).
(5-bromo-2-ethoxyphenyl) (furan-2-yl) methanol;
1 H NMR (CDCl 3 ); δ 7.60-7.30 (m, 3H), 6.80-6.70 (m, 1H), 6.40-6.30 (m, 1H), 6.20-5.90 (m, 2H), 4.20-3.90 ( m, 2H), 3.15-2.85 (m, 1H), 1.40-1.30 (m, 3H).
(5-bromo-2-methylphenyl) (furan-2-yl) methanol;
1 H NMR (CDCl 3 ); δ 7.80-7.70 (m, 1H), 7.45-7.20 (m, 2H), 7.10-6.95 (m, 1H), 6.40-6.25 (m, 1H), 6.10-5.90 ( m, 2H), 2.45-2.35 (m, 1H), 2.19 (m, 3H).
　工程２：５－（５－ブロモ－２－メトキシフェニル）－４－ヒドロキシシクロペンタ－２－エン－１－オンの製造
　（５－ブロモ－２－メトキシフェニル）（フラン－２－イル）メタノール１０５ｇを、国際公開第２０１６／０９８８９９号記載の方法で反応させることにより、目的物１００ｇを黒色油状物として得た。
1H NMR(CDCl3)；δ.7.60-7.55 (m, 1H), 7.42-7.24 (m, 2H), 6.77-6.72 (m, 1H), 6.35-6.30 (m, 1H), 5.00 (brs, 1H), 3.72 (s, 3H), 3.41-3.40 (m, 1H). Step 2: Preparation of 5- (5-bromo-2-methoxyphenyl) -4-hydroxycyclopent-2-en-1-one (5-bromo-2-methoxyphenyl) (furan-2-yl) methanol 105 g Was reacted by the method described in International Publication No. 2016/098899 to obtain 100 g of the objective product as a black oil.
1 H NMR (CDCl 3 ); δ.7.60-7.55 (m, 1H), 7.42-7.24 (m, 2H), 6.77-6.72 (m, 1H), 6.35-6.30 (m, 1H), 5.00 (brs, 1H), 3.72 (s, 3H), 3.41-3.40 (m, 1H).
　同様の方法を用いて以下の化合物を製造した。
５－（５－ブロモ－２－フルオロルフェニル）－４－ヒドロキシシクロペンタ－２－エン－１－オン；
1H NMR(CDCl3)；δ7.63-7.60 (m, 1H), 7.48-7.23 (m, 2H), 6.99-6.84 (m, 1H), 6.39-6.37 (m, 1H), 5.10-4.96 (m, 1H), 3.57-3.46 (m, 1H), 2.55-.2.38 (brs, 1H).
５－（５－ブロモ－２－エトキシルフェニル）－４－ヒドロキシシクロペンタ－２－エン－１－オン；
1H NMR(CDCl3)；δ7.70-7.20 (m, 3H), 6.80-6.70 (m, 1H), 6.50-6.20 (m, 1H), 4.20-3.20 (m, 4H), 2.17 (s, 1H), 1.80-1.10 (m, 3H).
５－（５－ブロモ－２－メチルフェニル）－４－ヒドロキシシクロペンタ－２－エン－１－オン；
1H NMR(CDCl3)；δ7.80-6.90 (m, 4H), 6.40-6.25 (m, 1H), 5.00-4.90 (m, 1H), 3.75-3.55 (m, 1H), 2.50-2.00 (m, 3H). The following compounds were prepared using similar methods.
5- (5-bromo-2-fluorophenyl) -4-hydroxycyclopent-2-en-1-one;
1 H NMR (CDCl 3 ); δ7.63-7.60 (m, 1H), 7.48-7.23 (m, 2H), 6.99-6.84 (m, 1H), 6.39-6.37 (m, 1H), 5.10-4.96 ( m, 1H), 3.57-3.46 (m, 1H), 2.55-.2.38 (brs, 1H).
5- (5-bromo-2-ethoxylphenyl) -4-hydroxycyclopent-2-en-1-one;
1 H NMR (CDCl 3 ); δ 7.70-7.20 (m, 3H), 6.80-6.70 (m, 1H), 6.50-6.20 (m, 1H), 4.20-3.20 (m, 4H), 2.17 (s, 1H), 1.80-1.10 (m, 3H).
5- (5-bromo-2-methylphenyl) -4-hydroxycyclopent-2-en-1-one;
1 H NMR (CDCl 3 ); δ 7.80-6.90 (m, 4H), 6.40-6.25 (m, 1H), 5.00-4.90 (m, 1H), 3.75-3.55 (m, 1H), 2.50-2.00 ( m, 3H).
　工程３：２－（５－ブロモ－２－メトキシフェニル）シクロペンタ－４－エン－１，３－ジオンの製造
　５－（５－ブロモ－２－メトキシフェニル）－４－ヒドロキシシクロペンタ－２－エン－１－オン１００ｇを、国際公開第２０１６／０９８８９９号記載の方法で反応させることにより、目的物２２．７ｇを黄色固体として得た。
融点；１２３－１２５℃ Step 3: Preparation of 2- (5-bromo-2-methoxyphenyl) cyclopent-4-ene-1,3-dione 5- (5-Bromo-2-methoxyphenyl) -4-hydroxycyclopent-2-ene By reacting 100 g of 1-one by the method described in WO2016 / 098899, 22.7 g of the desired product was obtained as a yellow solid.
Melting point: 123-125 ° C
　同様の方法を用いて以下の化合物を製造した。
２－（５－ブロモ－２－フルオロフェニル）シクロペンタ－４－エン－１，３－ジオン；
融点；１１４－１１６℃
２－（５－ブロモ－２－エトキシフェニル）シクロペンタ－４－エン－１，３－ジオン；
融点；１４０－１４３℃
２－（５－ブロモ－２－メチルフェニル）シクロペンタ－４－エン－１，３－ジオン；
1H NMR(CDCl3)；δ7.50-7.30 (m, 3H), 7.20-7.05 (m, 1H), 6.95-6.85 (m, 1H), 4.14 (s, 1H), 2.35-2.20 (m, 3H). The following compounds were prepared using similar methods.
2- (5-bromo-2-fluorophenyl) cyclopent-4-ene-1,3-dione;
Melting point: 114-116 ° C
2- (5-bromo-2-ethoxyphenyl) cyclopent-4-ene-1,3-dione;
Melting point: 140-143 ° C
2- (5-bromo-2-methylphenyl) cyclopent-4-ene-1,3-dione;
1 H NMR (CDCl 3 ); δ 7.50-7.30 (m, 3H), 7.20-7.05 (m, 1H), 6.95-6.85 (m, 1H), 4.14 (s, 1H), 2.35-2.20 (m, 3H).
　本発明化合物は、前記製造法及び実施例に準じて合成することができる。合成例１乃至合成例８と同様に製造した本発明化合物の例を第５表乃至第８表に、更にそれらの製造中間体の例を第１０表及び第１１表に示すが、本発明に包含されるケトン若しくはオキシム化合物及びそれらの製造中間体はこれらのみに限定されるものではない。 The compound of the present invention can be synthesized according to the above production methods and examples. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 8 are shown in Tables 5 to 8, and examples of their production intermediates are shown in Tables 10 and 11. The included ketone or oxime compounds and their intermediates are not limited to these.
　尚、第５表～第８表中、Ｍｅとの記載はメチルを、Ｅｔとの記載はエチルを、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピルを、ｔ－Ｂｕ及びＢｕ－ｔはターシャリーブチルを、ｃ－Ｐｅｎ及びＰｅｎ－ｃはシクロペンチル基を、Ｈｅｘ－ｃはシクロヘキシル基を、Ｐｈはフェニル基を、「＝」は２重結合を、「≡」は３重結合をそれぞれ表す。 In Tables 5 to 8, Me indicates methyl, Et indicates ethyl, c-Pr and Pr-c indicate cyclopropyl, and t-Bu and Bu-t indicate tertiary butyl. , C-Pen and Pen-c represent a cyclopentyl group, Hex-c represents a cyclohexyl group, Ph represents a phenyl group, “=” represents a double bond, and “≡” represents a triple bond.
　表中、Ｄ１－１０８、Ｄ２－１、Ｄ２－３４、Ｄ２－５６、Ｄ２－１００、Ｄ２－１０１、Ｄ２－１０２、Ｄ２－１０８、Ｄ２－１０９、Ｄ２－１１０、Ｄ３－３ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－６０ａ及びＤ３－６０ｂで表される構造は下記の構造を表し、
Figure JPOXMLDOC01-appb-C000122
 　置換基Ｘ２、Ｘ３、Ｚf及びＺｊの置換位置は、上記の構造式において記された番号に対応するものであり、例えば表中、「Ｄ３－６０ｂ（６－Ｃｌ）」との記載は「６－クロロキノキサリン－２－イル」を表す。
　また、表中、「m.p.」の記載は「融点」を表し、「*1」の記載は「樹脂状」を表し、「decomp.」の記載は分解をそれぞれ意味する。 In the table, D1-108, D2-1, D2-34, D2-56, D2-100, D2-101, D2-102, D2-108, D2-109, D2-110, D3-3a, D3-18b , D3-21a, D3-21b, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-60a and D3-60b have the following structures: Represent,
Figure JPOXMLDOC01-appb-C000122
 The substitution positions of the substituents X 2 , X 3 , Z f and Z j correspond to the numbers described in the above structural formulas. For example, in the table, The description represents “6-chloroquinoxalin-2-yl”.
In the table, “mp” represents “melting point”, “* 1” represents “resin”, and “decomp.” Represents decomposition.
　〔第５表〕
Figure JPOXMLDOC01-appb-C000123
Figure JPOXMLDOC01-appb-T000124
Figure JPOXMLDOC01-appb-T000125
Figure JPOXMLDOC01-appb-T000126
Figure JPOXMLDOC01-appb-T000127
 [Table 5]
Figure JPOXMLDOC01-appb-C000123
Figure JPOXMLDOC01-appb-T000124
Figure JPOXMLDOC01-appb-T000125
Figure JPOXMLDOC01-appb-T000126
Figure JPOXMLDOC01-appb-T000127
　〔第６表〕
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-T000129
 [Table 6]
Figure JPOXMLDOC01-appb-C000128
Figure JPOXMLDOC01-appb-T000129
　〔第７表〕
Figure JPOXMLDOC01-appb-C000130
Figure JPOXMLDOC01-appb-T000131
 [Table 7]
Figure JPOXMLDOC01-appb-C000130
Figure JPOXMLDOC01-appb-T000131
　〔第８表〕
Figure JPOXMLDOC01-appb-C000132
Figure JPOXMLDOC01-appb-T000133
 [Table 8]
Figure JPOXMLDOC01-appb-C000132
Figure JPOXMLDOC01-appb-T000133
　第５表～第８表に記載された本発明化合物のうち、表中に融点の記載のない化合物の１Ｈ－ＮＭＲデータを第９表に示す。
　プロトン核磁気共鳴ケミカルシフト値は、基準物質としてＭｅ４Ｓｉ（テトラメチルシラン）を用い、重クロロホルム溶媒中で、３００ＭＨｚにて測定した。重メタノール溶媒で測定した化合物については、「（CD３OD）」と化合物No.に表記した。
　表中に記載の記号は次の意味を表す。ｓ：シングレット、ｂｒｓ：ブロードシングレット、ｄ：ダブレット、ｔ：トリプレット、ｍ：マルチプレット。「*3」の記載は、ヒドロキシのプロトンに相当するシグナルが観測されなかったことを表す。また、２種以上の構造異性体が存在する場合に解析が可能なシグナルについて、各々のケミカルシフト値を「and」で標記した。 Of the compounds of the present invention described in Tables 5 to 8, 1 H-NMR data of compounds having no melting point in the table are shown in Table 9.
The proton nuclear magnetic resonance chemical shift value was measured at 300 MHz in deuterated chloroform solvent using Me 4 Si (tetramethylsilane) as a reference substance. For compounds were measured in deuterated methanol solvent, it was expressed in the compound No. as "(CD 3 OD)".
The symbols described in the table have the following meanings. s: singlet, brs: broad singlet, d: doublet, t: triplet, m: multiplet. The description “* 3” indicates that a signal corresponding to a hydroxy proton was not observed. For signals that can be analyzed when two or more structural isomers are present, each chemical shift value is indicated by “and”.
Figure JPOXMLDOC01-appb-T000134
Figure JPOXMLDOC01-appb-T000134
Figure JPOXMLDOC01-appb-T000135
Figure JPOXMLDOC01-appb-T000135
Figure JPOXMLDOC01-appb-T000136
Figure JPOXMLDOC01-appb-T000136
Figure JPOXMLDOC01-appb-T000137
Figure JPOXMLDOC01-appb-T000137
Figure JPOXMLDOC01-appb-T000138
Figure JPOXMLDOC01-appb-T000138
Figure JPOXMLDOC01-appb-T000139
Figure JPOXMLDOC01-appb-T000139
Figure JPOXMLDOC01-appb-T000140
Figure JPOXMLDOC01-appb-T000140
Figure JPOXMLDOC01-appb-T000141
Figure JPOXMLDOC01-appb-T000141
Figure JPOXMLDOC01-appb-T000142
Figure JPOXMLDOC01-appb-T000142
Figure JPOXMLDOC01-appb-T000143
Figure JPOXMLDOC01-appb-T000143
Figure JPOXMLDOC01-appb-T000144
Figure JPOXMLDOC01-appb-T000144
Figure JPOXMLDOC01-appb-T000145
Figure JPOXMLDOC01-appb-T000145
Figure JPOXMLDOC01-appb-T000146
Figure JPOXMLDOC01-appb-T000146
　第１０表及び第１１表中、Ｍｅとの記載はメチルを、Ｅｔとの記載はエチルを、ｃ－Ｐｒ及びＰｒ－ｃはシクロプロピルをそれぞれ表し、Ｊ－１及びＪ－２で表される構造は、それぞれ下記の構造を表す。
Figure JPOXMLDOC01-appb-C000147
 　〔第１０表〕
Figure JPOXMLDOC01-appb-C000148
Figure JPOXMLDOC01-appb-T000149
 In Tables 10 and 11, description of Me represents methyl, description of Et represents ethyl, c-Pr and Pr-c represent cyclopropyl, and are represented by J-1 and J-2, respectively. Each structure represents the following structure.
Figure JPOXMLDOC01-appb-C000147
 [Table 10]
Figure JPOXMLDOC01-appb-C000148
Figure JPOXMLDOC01-appb-T000149
　〔第１１表〕
Figure JPOXMLDOC01-appb-C000150
Figure JPOXMLDOC01-appb-T000151
 [Table 11]
Figure JPOXMLDOC01-appb-C000150
Figure JPOXMLDOC01-appb-T000151
　第１０表及び第１１表に記載された本発明化合物の製造中間体のうち、表中に融点の記載のない化合物の１Ｈ－ＮＭＲデータを第１２表に示す。
　尚、プロトン核磁気共鳴ケミカルシフト値は、基準物質としてＭｅ４Ｓｉ（テトラメチルシラン）を用い、重クロロホルム溶媒又は、重メタノール溶媒中で、３００ＭＨｚにて測定した。尚、重メタノール溶媒で測定した化合物については、「（CD３OD）」と化合物No.に表記した。また、第１２表の記号は下記の意味を表す。ｓ：シングレット、ｂｒｓ：ブロードシングレット、ｄ：ダブレット、ｔ：トリプレット、ｍ：マルチプレット。尚、表中の「*3」と記載は、ヒドロキシのプロトンに相当するシグナルが観測されなかったことを表す。 Of the production intermediates of the compounds of the present invention described in Table 10 and Table 11, 1 H-NMR data of compounds whose melting points are not shown in the table are shown in Table 12.
The proton nuclear magnetic resonance chemical shift value was measured at 300 MHz in deuterated chloroform solvent or deuterated methanol solvent using Me 4 Si (tetramethylsilane) as a reference substance. Note that the compound was measured in deuterated methanol solvent, was expressed in the compound No. as "(CD 3 OD)". The symbols in Table 12 have the following meanings. s: singlet, brs: broad singlet, d: doublet, t: triplet, m: multiplet. In the table, “* 3” indicates that a signal corresponding to a hydroxy proton was not observed.
Figure JPOXMLDOC01-appb-T000152
Figure JPOXMLDOC01-appb-T000152
Figure JPOXMLDOC01-appb-T000153
Figure JPOXMLDOC01-appb-T000153
　[試験例]
　次に、本発明化合物の除草剤としての有用性について、以下の試験例において具体的に説明するが、本発明はこれらのみに限定されるものではない。 [Test example]
Next, the usefulness of the compound of the present invention as a herbicide will be specifically described in the following test examples, but the present invention is not limited thereto.
　試験例１　湛水条件における雑草発生前処理による除草効果試験
　１／１００００アールのワグネルポットに沖積土壌を入れた後、水を入れて混和し、水深４cmの湛水条件とした。ノビエ、ホタルイ及びコナギの種子を上記カップに混播した後、２．５葉期のイネ苗を移植した。播種当日、配合例２に準じて調製した本発明化合物の乳剤を所定の薬量になるように水で希釈し、水面に処理した。カップを２５乃至３０℃の温室内に置いて植物を育成し、薬剤処理３週間後に、各種植物に対する影響を下記の判定基準に従い調査した。ただし、化合物No. 1-063、1-067、1-068、1-074、1-075、1-076、1-077、1-079、1-080、1-083、1-084、1-085、1-086、1-087、1-088、1-089、1-090、1-091、1-092、1-093、1-094、1-098、1-099、1-100、1-101、1-102、1-116、1-118、1-119、1-120、1-121、1-122、1-124、1-125、1-126、1-127、1-128、1-130、1-134、1-135、1-138、1-139、2-005、2-006、2-007、2-011、2-015、3-004、4-005、4-007、4-008、4-009、4-015、4-019、4-020、4-021、4-022、4-023、4-024、4-025、4-027、4-028、4-029、4-030、4-031、4-032は薬剤処理２週間後に調査した。結果を第１３表に示す。
　判定基準
５　…　殺草率　９０％以上　（ほとんど完全枯死）
４　…　殺草率　７０％以上９０％未満
３　…　殺草率　４０％以上７０％未満
２　…　殺草率　２０％以上４０％未満
１　…　殺草率　　５％以上２０％未満
０　…　殺草率　　５％以下　（ほとんど効力なし） Test Example 1 Herbicidal effect test by pretreatment of weed generation under flooding conditions After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to make flooding conditions with a depth of 4 cm. After seeding nobies, firefly and koigi in the cup, rice seedlings at the 2.5 leaf stage were transplanted. On the day of sowing, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose and treated on the water surface. Plants were grown by placing the cup in a greenhouse at 25 to 30 ° C., and after 3 weeks of drug treatment, the effects on various plants were investigated according to the following criteria. Compound Nos. 1-063, 1-067, 1-068, 1-074, 1-075, 1-076, 1-077, 1-079, 1-080, 1-083, 1-084, 1 -085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-098, 1-099, 1-100 , 1-101, 1-102, 1-116, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-127, 1 -128, 1-130, 1-134, 1-135, 1-138, 1-139, 2-005, 2-006, 2-007, 2-011, 2-015, 3-004, 4-005 , 4-007, 4-008, 4-009, 4-015, 4-019, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-027, 4 -028, 4-029, 4-030, 4-031, and 4-032 were investigated 2 weeks after drug treatment. The results are shown in Table 13.
Criterion 5 ... More than 90% of herbicide rate
4 ... Herbicidal Rate 70% or more and less than 90% 3 ... Herbicidal Rate 40% or more and less than 70% 2 ... Herbicidal Rate 20% or more and less than 40% 1 ... Herbicidal Rate 5% or more but less than 20% 0 ... Herbicidal Rate 5% or less (almost effective) None)
　試験例２　湛水条件における雑草生育期処理による除草効果試験
　１／１００００アールのワグネルポットに沖積土壌を入れた後、水を入れて混和し、水深４cmの湛水条件とした。ノビエ、ホタルイ及びコナギの種子を上記カップに混播し、２５乃至３０℃の温室内に置いて植物を育成した。ノビエ、ホタルイ及びコナギが１乃至２葉期に達したとき、配合例２に準じて調製した本発明化合物の乳剤を所定の薬量になるように水で希釈し、水面に処理した。薬剤処理３週間後に、各種植物に対する影響を試験例１の判定基準に従って調査した。ただし、ただし、化合物No. 1-063、1-067、1-068、1-074、1-075、1-076、1-077、1-079、1-080、1-083、1-084、1-085、1-086、1-087、1-088、1-089、1-090、1-091、1-092、1-093、1-094、1-098、1-099、1-100、1-101、1-102、1-116、1-118、1-119、1-120、1-121、1-122、1-124、1-125、1-126、1-127、1-128、1-130、1-134、1-135、1-138、1-139、2-005、2-006、2-007、2-011、2-015、3-004、4-005、4-007、4-008、4-009、4-015、4-019、4-020、4-021、4-022、4-023、4-024、4-025、4-027、4-028、4-029、4-030、4-031、4-032は薬剤処理２週間後に調査した。結果を第１４表に示す。 Test Example 2 Herbicidal Effect Test by Weed Growth Season Treatment under Flooding Conditions After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to make a flooding condition with a depth of 4 cm. Nobies, firefly, and oak seeds were mixed in the cup and placed in a greenhouse at 25-30 ° C. to grow plants. When Nobies, Firefly and Konagi reached the 1st to 2nd leaf stage, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water so as to have a predetermined dosage and treated on the water surface. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. However, Compound Nos. 1-063, 1-067, 1-068, 1-074, 1-075, 1-076, 1-077, 1-079, 1-080, 1-083, 1-084 , 1-085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-098, 1-099, 1 -100, 1-101, 1-102, 1-116, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-127 , 1-128, 1-130, 1-134, 1-135, 1-138, 1-139, 2-005, 2-006, 2-007, 2-011, 2-015, 3-004, 4 -005, 4-007, 4-008, 4-009, 4-015, 4-019, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-027 4-028, 4-029, 4-030, 4-031, and 4-032 were investigated 2 weeks after drug treatment. The results are shown in Table 14.
　試験例３　茎葉処理による除草効果試験
　１／１００００アールのワグネルポットに沖積土壌を入れた後、水を入れて混和し、水深０．１乃至０．５cmの条件とした。イヌビエ、アゼガヤ、タマガヤツリ及びイネの種子を播種し、２５乃至３０℃の温室内に置いて植物を育成した。１４日間育成したのち、配合例２に準じて調製した本発明化合物の乳剤を所定の薬量になるように水で希釈し、茎葉部へ小型スプレーで均一に処理した。薬剤処理３週間後に、各種植物に対する影響を試験例１の判定基準に従って調査した。ただし、ただし、化合物No. 1-063、1-067、1-068、1-074、1-075、1-076、1-077、1-079、1-080、1-083、1-084、1-085、1-086、1-087、1-088、1-089、1-090、1-091、1-092、1-093、1-094、1-098、1-099、1-100、1-101、1-102、1-116、1-118、1-119、1-120、1-121、1-122、1-124、1-125、1-126、1-127、1-128、1-130、1-134、1-135、1-138、1-139、2-005、2-006、2-007、2-011、2-015、3-004、4-005、4-007、4-008、4-009、4-015、4-019、4-020、4-021、4-022、4-023、4-024、4-025、4-027、4-028、4-029、4-030、4-031、4-032は薬剤処理２週間後に調査した。結果を第１５表に示す。 Test Example 3 Herbicidal effect test by foliage treatment After alluvial soil was put into a 1/10000 are Wagner pot, water was added and mixed to obtain a water depth of 0.1 to 0.5 cm. Inobie, Azegaya, Tamagayatsuri, and rice seeds were sown and placed in a greenhouse at 25 to 30 ° C. to grow plants. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. However, Compound Nos. 1-063, 1-067, 1-068, 1-074, 1-075, 1-076, 1-077, 1-079, 1-080, 1-083, 1-084 , 1-085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-098, 1-099, 1 -100, 1-101, 1-102, 1-116, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-127 , 1-128, 1-130, 1-134, 1-135, 1-138, 1-139, 2-005, 2-006, 2-007, 2-011, 2-015, 3-004, 4 -005, 4-007, 4-008, 4-009, 4-015, 4-019, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-027 4-028, 4-029, 4-030, 4-031, and 4-032 were investigated 2 weeks after drug treatment. The results are shown in Table 15.
　試験例４　土壌処理による除草効果試験
　縦２１cm、横１３cm、深さ７cmのプラスチック製箱に殺菌した洪積土壌を入れ、メヒシバ、エノコログサ、イヌビエ、カラスムギ、ブラックグラス、イタリアンライグラス、セイヨウヌカボ、イチビ、アオゲイトウ、シロザ、ハコベ、ヤエムグラ、オオイヌノフグリ、トウモロコシ、ダイズ、イネ、コムギ、ビート及びナタネの種子をそれぞれスポット状に播種し、約１．５cm覆土した。次いで配合例２に準じて調製した本発明化合物の乳剤を所定の薬量になるように水で希釈し、土壌表面へ小型スプレーで均一に処理した。プラスチック製箱を２５乃至３０℃の温室内に置いて植物を育成し、薬剤処理３週間後に、各種植物に対する影響を試験例１の判定基準に従って調査した。ただし、化合物No. 1-063、1-067、1-068、1-074、1-075、1-076、1-077、1-079、1-080、1-083、1-084、1-085、1-086、1-087、1-088、1-089、1-090、1-091、1-092、1-093、1-094、1-098、1-099、1-100、1-101、1-102、1-116、1-118、1-119、1-120、1-121、1-122、1-124、1-125、1-126、1-127、1-128、1-130、1-134、1-135、1-138、1-139、2-005、2-006、2-007、2-011、2-015、3-004、4-005、4-007、4-008、4-009、4-015、4-019、4-020、4-021、4-022、4-023、4-024、4-025、4-027、4-028、4-029、4-030、4-031、4-032は薬剤処理２週間後に調査した。結果を第１６表に示す。 Test Example 4 Herbicidal Effect Test by Soil Treatment Put sterilized large soil in a plastic box 21cm long, 13cm wide and 7cm deep, and then squirrel, green crocodile, black mulberry, blackgrass, Italian ryegrass, black croaker, ichibi, The seeds of Aogateto, Shiroza, Jacobe, Jaegula, Giant corn, corn, soybean, rice, wheat, beet and rapeseed were sown in spots and covered with about 1.5 cm. Next, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the soil surface. Plants were grown by placing plastic boxes in a greenhouse at 25 to 30 ° C., and after 3 weeks of chemical treatment, the effects on various plants were investigated according to the criteria of Test Example 1. Compound Nos. 1-063, 1-067, 1-068, 1-074, 1-075, 1-076, 1-077, 1-079, 1-080, 1-083, 1-084, 1 -085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-098, 1-099, 1-100 , 1-101, 1-102, 1-116, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-127, 1 -128, 1-130, 1-134, 1-135, 1-138, 1-139, 2-005, 2-006, 2-007, 2-011, 2-015, 3-004, 4-005 , 4-007, 4-008, 4-009, 4-015, 4-019, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-027, 4 -028, 4-029, 4-030, 4-031, and 4-032 were investigated 2 weeks after drug treatment. The results are shown in Table 16.
　試験例５　茎葉処理による除草効果試験
　縦２１cm、横１３cm、深さ７cmのプラスチック製箱に殺菌した洪積土壌を入れ、メヒシバ、エノコログサ、イヌビエ、カラスムギ、ブラックグラス、イタリアンライグラス、セイヨウヌカボ、イチビ、アオゲイトウ、シロザ、ハコベ、ヤエムグラ、オオイヌノフグリ、トウモロコシ、ダイズ、イネ、コムギ、ビート及びナタネの種子をそれぞれスポット状に播種し、約１．５cm覆土した後、２５乃至３０℃の温室内において植物を育成した。１４日間育成したのち，配合例２に準じて調製した本発明化合物の乳剤を所定の薬量になるように水で希釈し、茎葉部へ小型スプレーで均一に処理した。薬剤処理３週間後に、各種植物に対する影響を試験例１の判定基準に従って調査した。ただし、化合物No. 1-063、1-067、1-068、1-074、1-075、1-076、1-077、1-079、1-080、1-083、1-084、1-085、1-086、1-087、1-088、1-089、1-090、1-091、1-092、1-093、1-094、1-098、1-099、1-100、1-101、1-102、1-116、1-118、1-119、1-120、1-121、1-122、1-124、1-125、1-126、1-127、1-128、1-130、1-134、1-135、1-138、1-139、2-005、2-006、2-007、2-011、2-015、3-004、4-005、4-007、4-008、4-009、4-015、4-019、4-020、4-021、4-022、4-023、4-024、4-025、4-027、4-028、4-029、4-030、4-031、4-032は薬剤処理２週間後に調査した。結果を第１７表に示す。
　尚、第１３表乃至第１７表中の記号は以下の意味を表す。
Ａ：ノビエ、Ｂ：ホタルイ、Ｃ：コナギ、Ｄ：アゼガヤ、Ｅ：コゴメガヤツリ、Ｆ：メヒシバ、Ｇ：エノコログサ、Ｈ：イヌビエ、Ｉ：カラスムギ、Ｊ：ブラックグラス、Ｋ：イタリアンライグラス、Ｌ：セイヨウヌカボ、Ｍ：イチビ、Ｎ：アオゲイトウ、Ｏ：シロザ、Ｐ：ハコベ、Ｑ：ヤエムグラ、Ｒ：オオイヌノフグリ、ａ：移植イネ、b:直播イネ、ｃ：トウモロコシ、ｄ：ダイズ、e：コムギ、f：ビート、g：ナタネ
　また処理薬量（ｇ／ｈａ）とは、１ヘクタール（１ｈａ）当たりに換算したときに、記載した数値のグラム（ｇ）数だけ処理されるように濃度を調整したことを表す。 Test Example 5 Herbicidal effect test by foliar treatment Put sterilized large soil in a plastic box 21cm long, 13cm wide, 7cm deep, pearl bark, green croaker, barnyardgrass, oats, blackgrass, Italian ryegrass, Atlantic calyx, Ichibi, Seeds of Aogateto, Shiroza, Jacobe, Jaegula, Giant corn, corn, soybean, rice, wheat, beet and rapeseed are spotted, covered with about 1.5 cm, and then grown in a greenhouse at 25 to 30 ° C did. After growing for 14 days, the emulsion of the compound of the present invention prepared according to Formulation Example 2 was diluted with water to a predetermined dose, and uniformly treated with a small spray on the foliage. Three weeks after the drug treatment, the influence on various plants was investigated according to the criteria of Test Example 1. Compound Nos. 1-063, 1-067, 1-068, 1-074, 1-075, 1-076, 1-077, 1-079, 1-080, 1-083, 1-084, 1 -085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-098, 1-099, 1-100 , 1-101, 1-102, 1-116, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-127, 1 -128, 1-130, 1-134, 1-135, 1-138, 1-139, 2-005, 2-006, 2-007, 2-011, 2-015, 3-004, 4-005 , 4-007, 4-008, 4-009, 4-015, 4-019, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-027, 4 -028, 4-029, 4-030, 4-031, and 4-032 were investigated 2 weeks after drug treatment. The results are shown in Table 17.
The symbols in Tables 13 to 17 have the following meanings.
A: Nobies, B: Firefly, C: Konagi, D: Azegaya, E: Kogomegatsuri, F: Barbet, G: Enokirogusa, H: Inubie, I: Oats, J: Blackgrass, K: Italian ryegrass, L: Atlantic calyx , M: Ichibi, N: Blue-headed toe, O: Shiroza, P: Jacobe, Q: Yamgra, R: Giant corn, a: Transplanted rice, b: Directly sown rice, c: Corn, d: Soy, e: Wheat, f: Beet , G: rapeseed The treatment dose (g / ha) represents that the concentration was adjusted so that the number of grams (g) described was processed when converted per hectare (1 ha). .
Figure JPOXMLDOC01-appb-T000154
Figure JPOXMLDOC01-appb-T000154
Figure JPOXMLDOC01-appb-T000155
Figure JPOXMLDOC01-appb-T000155
Figure JPOXMLDOC01-appb-T000156
Figure JPOXMLDOC01-appb-T000156
Figure JPOXMLDOC01-appb-T000157
Figure JPOXMLDOC01-appb-T000157
Figure JPOXMLDOC01-appb-T000158
Figure JPOXMLDOC01-appb-T000158
Figure JPOXMLDOC01-appb-T000159
Figure JPOXMLDOC01-appb-T000159
Figure JPOXMLDOC01-appb-T000160
Figure JPOXMLDOC01-appb-T000160
Figure JPOXMLDOC01-appb-T000161
Figure JPOXMLDOC01-appb-T000161
Figure JPOXMLDOC01-appb-T000162
Figure JPOXMLDOC01-appb-T000162
Figure JPOXMLDOC01-appb-T000163
Figure JPOXMLDOC01-appb-T000163
Figure JPOXMLDOC01-appb-T000164
Figure JPOXMLDOC01-appb-T000164
Figure JPOXMLDOC01-appb-T000165
Figure JPOXMLDOC01-appb-T000165
Figure JPOXMLDOC01-appb-T000166
Figure JPOXMLDOC01-appb-T000166
Figure JPOXMLDOC01-appb-T000167
Figure JPOXMLDOC01-appb-T000167
Figure JPOXMLDOC01-appb-T000168
Figure JPOXMLDOC01-appb-T000168
Figure JPOXMLDOC01-appb-T000169
Figure JPOXMLDOC01-appb-T000169
Figure JPOXMLDOC01-appb-T000170
Figure JPOXMLDOC01-appb-T000170
Figure JPOXMLDOC01-appb-T000171
Figure JPOXMLDOC01-appb-T000171
Figure JPOXMLDOC01-appb-T000172
Figure JPOXMLDOC01-appb-T000172
Figure JPOXMLDOC01-appb-T000173
Figure JPOXMLDOC01-appb-T000173
　本発明のケトン若しくはオキシム化合物は新規な化合物であり、イネ用、トウモロコシ用、ダイズ用、麦用、ビート用及びナタネ用の選択性除草剤として有用である。 The ketone or oxime compound of the present invention is a novel compound and is useful as a selective herbicide for rice, corn, soybean, wheat, beet and rapeseed.

Claims (18)

  1. 　式（１）：
    Figure JPOXMLDOC01-appb-C000001
     ［式中、Ｂは、Ｂ－１又はＢ－２のいずれかで示される環を表し、
    Figure JPOXMLDOC01-appb-C000002
     　Ｑは、酸素原子、硫黄原子又はＮＯＲ７を表し、
    　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５で任意に置換された（Ｃ２～Ｃ６）アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ、－Ｃ（Ｏ）Ｒ２、－Ｃ（Ｓ）Ｒ２、－Ｐ（Ｏ）（ＯＲ３ｃ）２又は－Ｐ（Ｓ）（ＯＲ３ｃ）２を表し、
    　Ｒ１ａは、Ｃ１～Ｃ８アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ａで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１ｂ、Ｒ１ｃ、Ｒ１ｄ及びＲ１ｅは、各々独立してＣ１～Ｃ８アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ２は、水素原子、Ｃ１～Ｃ８アルキル、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ｆで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ｆで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルキルカルボニル、ベンゾイル、（Ｚｆ）ｑｆで置換されたベンゾイル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、－Ｎ（Ｒ４ａ）Ｒ３ａ、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｄ２－１～Ｄ２－５６、Ｄ２－１００Ｄ２－１００～Ｄ２－１０６及びＤ２－１０７は、下記の構造で表される環を表し、
    Figure JPOXMLDOC01-appb-C000003
    Figure JPOXMLDOC01-appb-C000004
     　Ｒ３ａ、Ｒ３ｂ、Ｒ４ａ及びＲ４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ｇで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｇで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ５ｇで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ５ｇで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ５ｇで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ３ｃは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
    　Ｒ５は、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、－ＯＲ３１、－Ｓ（Ｏ）ｒ２Ｒ３１、ベンゾイル、（Ｚｆ）ｑｆで置換されたベンゾイル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ５ａ、Ｒ５ｂ及びＲ５ｇは、各々独立してハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ１～Ｃ６アルコキシ、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７表し、
    　Ｒ５ｆは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＯＲｆ、－Ｓ（Ｏ）ｒ２Ｒｆ、－Ｎ（Ｒ４ｆ）Ｒ３ｆ、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ６は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ６ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ６ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ６ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ６ｂは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ３１ｂ、－Ｓ（Ｏ）ｒ１Ｒ３１ｂ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、ベンゾイル、（Ｚｊ）ｑｊで置換されたベンゾイル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ７ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ７ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、－Ｓ（Ｏ）ｒ１Ｒ１５ａ、－Ｃ（Ｏ）ＯＲ１５ｂ、－Ｃ（Ｓ）ＯＲ１５ｂ、－Ｃ（Ｏ）ＳＲ１５ｂ、－Ｃ（Ｓ）ＳＲ１５ｂ、－Ｃ（Ｏ）Ｒ１６、－Ｃ（Ｓ）Ｒ１６、－Ｐ（Ｏ）（ＯＲ１７ｃ）２、－Ｐ（Ｓ）（ＯＲ１７ｃ）２、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－４～Ｄ２－６、Ｄ２－８～Ｄ２－１０、Ｄ２－１２～Ｄ２－１９、Ｄ２－２１、Ｄ２－２３、Ｄ２－２５、Ｄ２－２７、Ｄ２－３０～Ｄ２－５５又はＤ２－５６を表し
    　Ｒ７ｂは、ハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－ＯＲ３１ｂ、－Ｓ（Ｏ）ｒ１Ｒ３１ｂ、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、ベンゾイル、（Ｚｊ）ｑｊで置換されたベンゾイル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００、Ｄ２－１０１～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ、Ｒ９ｂ、Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１５ａは、Ｃ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ１８）Ｒ１７、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１５ｂは、各々独立してＣ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１６は、水素原子、Ｃ１～Ｃ８アルキル、Ｒ２０ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０ｆで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０ｆで任意に置換された（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルキルカルボニル、ベンゾイル、（Ｚｆ）ｑｆで置換されたベンゾイル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、－Ｎ（Ｒ１８）Ｒ１７、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１７及びＲ１８は、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ３～Ｃ８シクロアルケニル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルケニル、Ｃ２～Ｃ６アルキニル、Ｒ２０で任意に置換された（Ｃ２～Ｃ６）アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１７ｃは、Ｃ１～Ｃ６アルキル又はフェニルを表し、
    　Ｒ２０は、各々独立してハロゲン原子、シアノ、ニトロ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ１～Ｃ６アルコキシ、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ２０ｆは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＯＲｆ、－Ｓ（Ｏ）ｒ１Ｒｆ、－Ｎ（Ｒ４ｆ）Ｒ３ｆ、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ３１は、水素原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル、－Ｃ（Ｏ）Ｒ３７、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
    　Ｒ３１ｂは、水素原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル、－Ｃ（Ｏ）Ｒ３７、フェニル又は（Ｚｉ）ｑｉで置換されたフェニルを表し、
    　Ｒ３７は、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ３～Ｃ８シクロアルキルオキシ、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
    　Ｒｆは、水素原子、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、フェニル（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルキルカルボニル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、Ｄ２－１～Ｄ２－５６、Ｄ２－１００、Ｄ２－１０１～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ３ｆ及びＲ４ｆは、各々独立してＣ１～Ｃ６アルキル又はベンゾイルを表し、
    　Ｚ４は、水素原子、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル又は－ＮＨ２を表し、
    　Ｚ５、Ｚ６及びＺ８は、各々独立して水素原子、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
    　Ｚ７は、－ＯＲ４１又は－Ｓ（Ｏ）ｒＲ４１を表し、
    　Ｒ４１は、Ｄ３－１ａ、Ｄ３－１ｂ、Ｄ３－２ａ、Ｄ３－２ｂ、Ｄ３－３ａ、Ｄ３－３ｂ、Ｄ３－４ａ、Ｄ３－４ｂ、Ｄ３－１８ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－２７ａ、Ｄ３－２７ｂ、Ｄ３－３２ａ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－５８ｂ、Ｄ３－５９ａ、Ｄ３－６０ａ、Ｄ３－６０ｂ又はＤ３－６５ａを表し、
    　Ｄ３－１ａ、Ｄ３－１ｂ、Ｄ３－２ａ、Ｄ３－２ｂ、Ｄ３－３ａ、Ｄ３－３ｂ、Ｄ３－４ａ、Ｄ３－４ｂ、Ｄ３－１８ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－２７ａ、Ｄ３－２７ｂ、Ｄ３－３２ａ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－５８ｂ、Ｄ３－５９ａ、Ｄ３－６０ａ、Ｄ３－６０ｂ及びＤ３－６５ａは、下記の構造で表される環を表し、
    Figure JPOXMLDOC01-appb-C000005
     　Ｘ２は、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｆ２、ｆ３、ｆ４、ｆ５、ｆ７、ｆ８、ｆ９、ｆ１０又はｆ１１が２以上の整数を表すとき、各々のＸ２は互いに同一であっても又は互いに相異なってもよく、更に、２つのＸ２が隣接する場合には、隣接する２つのＸ２は－ＣＨ＝ＣＨＣＨ＝ＣＨ－を形成することにより、それぞれのＸ２が結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子はハロゲン原子又はＣ１～Ｃ６アルキルによって任意に置換されていてもよく、
    　Ｘ３は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル又はフェニルを表し、ｔ２、ｔ３、ｔ４又はｔ５が２以上の整数を表すとき、各々のＸ３は互いに同一であっても又は互いに相異なってもよく、
    　Ｘ２ａ及びＸ４は、各々独立して水素原子、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルキルカルボニル、Ｃ１～Ｃ６アルコキシカルボニル又はフェニルを表し、
    　Ｚａは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｑａが２以上の整数を表すとき、各々のＺａは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺａが隣接する場合には、隣接する２つのＺａは－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺａが結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル又はＣ１～Ｃ６アルキルスルホニルによって任意に置換されてもよく、
    　Ｚｂは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｑｂが２以上の整数を表すとき、各々のＺｂは互いに同一であっても又は互いに相異なってもよく、
    　Ｚｆは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ、－ＯＲ５１、－Ｓ（Ｏ）ｒ２Ｒ５１又はフェニルを表し、ｑｆが２以上の整数を表すとき、各々のＺｆは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺｆが隣接する場合には、隣接する２つのＺｆは－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺｆが結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル又はＣ１～Ｃ６アルキルスルホニルによって任意に置換されてもよく、
    　Ｚｊは、ハロゲン原子、シアノ、ニトロ、－ＣＨＯ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、ハロ（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ、ハロ（Ｃ１～Ｃ６）アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、ハロ（Ｃ１～Ｃ６）アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、ハロ（Ｃ１～Ｃ６）アルキルスルホニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル、ジ（Ｃ１～Ｃ６）アルキルアミノカルボニル、－ＮＨ２、Ｃ１～Ｃ６アルキルアミノ、ジ（Ｃ１～Ｃ６）アルキルアミノ、Ｃ１～Ｃ６アルキルカルボニルアミノ又はフェニルを表し、ｑｊが２以上の整数を表すとき、各々のＺｊは互いに同一であっても又は互いに相異なってもよく、更に、２つのＺｊが隣接する場合には、隣接する２つのＺｊは－Ｎ＝ＣＨＣＨ＝ＣＨ－，－ＣＨ＝ＮＣＨ＝ＣＨ－，－Ｎ＝ＮＣＨ＝ＣＨ－，－ＣＨ＝ＮＮ＝ＣＨ－，－Ｎ＝ＣＨＣＨ＝Ｎ－又は－Ｎ＝ＣＨＮ＝ＣＨ－を形成することにより、それぞれのＺｊが結合する炭素原子と共に６員環を形成してもよく、このとき、環を形成する各々の炭素原子に結合した水素原子は、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル又はＣ１～Ｃ６アルキルスルホニルによって任意に置換されてもよく、
    　Ｒ５１は、Ｃ２～Ｃ６アルケニル、ハロ（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、ハロ（Ｃ２～Ｃ６）アルキニル、フェニル（Ｃ１～Ｃ６）アルキル又はフェニルを表し、
    　ｆ１、ｐ１、ｐ２及びｔ１は、各々独立して０又は１の整数を表し、
    　ｆ２、ｒ、ｒ１、ｒ２及びｔ２は、各々独立して０、１又は２の整数を表し、
    　ｍ、ｎ、ｆ３及びｔ３は、各々独立して０、１、２又は３の整数を表し、
    　ｆ４及びｔ４は、各々独立して０、１、２、３又は４の整数を表し、
    　ｆ５及びｔ５は、各々独立して０、１、２、３、４又は５の整数を表し、
    　ｑａ、ｑｂ、ｑｆ及びｑｊは、各々独立して１、２、３、４又は５の整数を表し、
    　ｆ６は、０、１、２、３、４、５又は６の整数を表し、
    　ｆ７は、０、１、２、３、４、５、６又は７の整数を表し、
    　ｆ８は、０、１、２、３、４、５、６、７又は８の整数を表し、
    　ｆ９は、０、１、２、３、４、５、６、７、８又は９の整数を表し、
    　ｆ１０は、０、１、２、３、４、５、６、７、８、９又は１０の整数を表し、
    　ｆ１１は、０、１、２、３、４、５、６、７、８、９、１０又は１１の整数を表し、
    　ｆ１２は、０、１、２、３、４、５、６、７、８、９、１０、１１又は１２の整数を表す。］で表されるケトン若しくはオキシム化合物又はそれらの塩。     Formula (1):
    Figure JPOXMLDOC01-appb-C000001
     [Wherein B represents a ring represented by either B-1 or B-2;
    Figure JPOXMLDOC01-appb-C000002
     Q is an oxygen atom, sulfur atom or NOR 7 Represents
    A is a hydrogen atom, C 1 ~ C 6 Alkyl, R 5 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, -S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e , -C (O) R 2 , -C (S) R 2 , -P (O) (OR 3c ) 2 Or -P (S) (OR 3c ) 2 Represents
    R 1a Is C 1 ~ C 8 Alkyl, R 5a Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5a Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5a Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5a Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5a Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 4b ) R 3b , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
    R 1b , R 1c , R 1d And R 1e Are each independently C 1 ~ C 8 Alkyl, R 5b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5b Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 2 Is a hydrogen atom, C 1 ~ C 8 Alkyl, R 5f Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5f Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5f Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5f Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5f Optionally substituted with (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkylcarbonyl, benzoyl, (Z f ) qf Benzoyl, phenyl, (Z f ) qf Substituted with phenyl, -N (R 4a ) R 3a , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
    D2-1 to D2-56, D2-100, D2-100 to D2-106, and D2-107 each represent a ring represented by the following structure:
    Figure JPOXMLDOC01-appb-C000003
    Figure JPOXMLDOC01-appb-C000004
     R 3a , R 3b , R 4a And R 4b Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 5g Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 5g Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 5g Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 5g Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 5g Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 3c Is C 1 ~ C 6 Represents alkyl or phenyl,
    R 5 Is a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, —C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, -OR 31 , -S (O) r2 R 31 , Benzoyl, (Z f ) qf Benzoyl, phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 5a , R 5b And R 5g Each independently represents a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 1 ~ C 6 Alkoxy, phenyl, (Z b ) qb Phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 5f Is a halogen atom, cyano, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, —C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -OR f , -S (O) r2 R f , -N (R 4f ) R 3f , Phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 6 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 6b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 6b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 6b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 6b Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 6b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z j ) qj Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 6b Is a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, -OR 31b , -S (O) r1 R 31b , C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, phenyl, (Z j ) qj Phenyl, benzoyl, substituted with (Z j ) qj Represents benzoyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107 substituted with
    R 7 Is a hydrogen atom, C 1 ~ C 6 Alkyl, R 7b Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 7b Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 7b Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 7b Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 7b Optionally substituted with (C 2 ~ C 6 ) Alkynyl, -S (O) r1 R 15a , -C (O) OR 15b , -C (S) OR 15b , -C (O) SR 15b , -C (S) SR 15b , -C (O) R 16 , -C (S) R 16 , -P (O) (OR 17c ) 2 , -P (S) (OR 17c ) 2 , Phenyl, (Z j ) qj Phenyl, D2-1, D2-2, D2-4 to D2-6, D2-8 to D2-10, D2-12 to D2-19, D2-21, D2-23, D2-25, D2-27, D2-30 to D2-55 or D2-56
    R 7b Is a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, -OR 31b , -S (O) r1 R 31b , -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, phenyl, (Z j ) qj Phenyl, benzoyl, substituted with (Z j ) qj Represents benzoyl, D2-1 to D2-56, D2-100, D2-101 to D2-106 or D2-107, substituted with
    R 8a , R 8b , R 9a , R 9b , R 10 , R 11 And R 12 Each independently represents a hydrogen atom, a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, -OH, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, phenyl, (Z j ) qj Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 15a Is C 1 ~ C 8 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z a ) qa Substituted with phenyl, -N (R 18 ) R 17 , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
    R 15b Are each independently C 1 ~ C 8 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 16 Is a hydrogen atom, C 1 ~ C 8 Alkyl, R 20f Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20f Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20f Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20f Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20f Optionally substituted with (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkylcarbonyl, benzoyl, (Z f ) qf Benzoyl, phenyl, (Z f ) qf Substituted with phenyl, -N (R 18 ) R 17 , D2-1 to D2-56, D2-100 to D2-106 or D2-107,
    R 17 And R 18 Are each independently a hydrogen atom, C 1 ~ C 6 Alkyl, R 20 Optionally substituted with (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkenyl, C 3 ~ C 8 Cycloalkenyl, R 20 Optionally substituted with (C 3 ~ C 8 ) Cycloalkenyl, C 2 ~ C 6 Alkynyl, R 20 Optionally substituted with (C 2 ~ C 6 ) Alkynyl, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 17c Is C 1 ~ C 6 Represents alkyl or phenyl,
    R 20 Each independently represents a halogen atom, cyano, nitro, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 1 ~ C 6 Alkoxy, phenyl, (Z b ) qb Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 20f Is a halogen atom, cyano, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, —C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, C 1 ~ C 6 Alkylcarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -OR f , -S (O) r1 R f , -N (R 4f ) R 3f , Phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100 to D2-106 or D2-107, substituted with
    R 31 Is a hydrogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl, —C (O) R 37 , Phenyl or (Z f ) qf Represents phenyl substituted with
    R 31b Is a hydrogen atom, C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, C 1 ~ C 6 Alkoxy (C 1 ~ C 4 ) Alkyl, —C (O) R 37 , Phenyl or (Z i ) qi Represents phenyl substituted with
    R 37 Is C 1 ~ C 6 Alkyl, C 1 ~ C 6 Alkoxy, C 3 ~ C 8 Cycloalkyloxy, phenyl or (Z f ) qf Represents phenyl substituted with
    R f Is a hydrogen atom, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, phenyl (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkylcarbonyl, phenyl, (Z f ) qf Represents phenyl, D2-1 to D2-56, D2-100, D2-101 to D2-106 or D2-107 substituted with
    R 3f And R 4f Are each independently C 1 ~ C 6 Represents alkyl or benzoyl,
    Z 4 Is a hydrogen atom, halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, C 2 ~ C 6 Alkenyl, C 2 ~ C 6 Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylthio, halo (C 1 ~ C 6 ) Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfonyl or -NH 2 Represents
    Z 5 , Z 6 And Z 8 Each independently represents a hydrogen atom, a halogen atom, or C 1 ~ C 6 Alkyl, C 3 ~ C 8 Cycloalkyl or C 1 ~ C 6 Represents alkoxy,
    Z 7 Is -OR 41 Or -S (O) r R 41 Represents
    R 41 Are D3-1a, D3-1b, D3-2a, D3-2b, D3-3a, D3-3b, D3-4a, D3-4b, D3-18a, D3-18b, D3-21a, D3-21b, D3-27a, D3-27b, D3-32a, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-58b, D3-59a, D3-60a, D3- 60b or D3-65a,
    D3-1a, D3-1b, D3-2a, D3-2b, D3-3a, D3-3b, D3-4a, D3-4b, D3-18a, D3-18b, D3-21a, D3-21b, D3- 27a, D3-27b, D3-32a, D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-58b, D3-59a, D3-60a, D3-60b and D3-65a represents a ring represented by the following structure:
    Figure JPOXMLDOC01-appb-C000005
     X 2 Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 X represents alkylcarbonylamino or phenyl, and when f2, f3, f4, f5, f7, f8, f9, f10 or f11 represents an integer of 2 or more, each X 2 May be the same as or different from each other, and two X 2 Are adjacent, the two adjacent X 2 Form -CH = CHCH = CH- 2 A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom or C 1 ~ C 6 Optionally substituted by alkyl,
    X 3 Is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, C 1 ~ C 6 Represents alkoxycarbonyl or phenyl, and when t2, t3, t4 or t5 represents an integer of 2 or more, each X 3 May be the same or different from each other,
    X 2a And X 4 Each independently represents a hydrogen atom, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkylcarbonyl, C 1 ~ C 6 Represents alkoxycarbonyl or phenyl,
    Z a Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 When Z represents an alkylcarbonylamino or phenyl and qa represents an integer of 2 or more, each Z a May be the same as or different from each other, and two Z a Are adjacent to each other, two adjacent Z a Form -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- By doing each Z a A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl or C 1 ~ C 6 Optionally substituted by alkylsulfonyl,
    Z b Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 When Z represents an alkylcarbonylamino or phenyl and qb represents an integer of 2 or more, each Z b May be the same or different from each other,
    Z f Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 Alkylcarbonylamino, -OR 51 , -S (O) r2 R 51 Or phenyl, and when qf represents an integer of 2 or more, each Z f May be the same as or different from each other, and two Z f Are adjacent to each other, two adjacent Z f Form -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- By doing each Z f A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl or C 1 ~ C 6 Optionally substituted by alkylsulfonyl,
    Z j Is a halogen atom, cyano, nitro, —CHO, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 3 ~ C 8 Cycloalkyl, Halo (C 3 ~ C 8 ) Cycloalkyl, C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, C 1 ~ C 6 Alkoxy, halo (C 1 ~ C 6 ) Alkoxy, C 1 ~ C 6 Alkylthio, halo (C 1 ~ C 6 ) Alkylthio, C 1 ~ C 6 Alkylsulfinyl, halo (C 1 ~ C 6 ) Alkylsulfinyl, C 1 ~ C 6 Alkylsulfonyl, halo (C 1 ~ C 6 ) Alkylsulfonyl, C 1 ~ C 6 Alkylcarbonyl, -C (O) OH, C 1 ~ C 6 Alkoxycarbonyl, —C (O) NH 2 , C 1 ~ C 6 Alkylaminocarbonyl, di (C 1 ~ C 6 ) Alkylaminocarbonyl, -NH 2 , C 1 ~ C 6 Alkylamino, di (C 1 ~ C 6 ) Alkylamino, C 1 ~ C 6 When Z represents an alkylcarbonylamino or phenyl and qj represents an integer of 2 or more, each Z j May be the same as or different from each other, and two Z j Are adjacent to each other, two adjacent Z j Form -N = CHCH = CH-, -CH = NCH = CH-, -N = NCH = CH-, -CH = NN = CH-, -N = CHCH = N- or -N = CHN = CH- By doing each Z j A 6-membered ring may be formed together with the carbon atom to which is bonded, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is a halogen atom, cyano, nitro, C 1 ~ C 6 Alkyl, halo (C 1 ~ C 6 ) Alkyl, C 1 ~ C 6 Alkoxy, C 1 ~ C 6 Alkylthio, C 1 ~ C 6 Alkylsulfinyl or C 1 ~ C 6 Optionally substituted by alkylsulfonyl,
    R 51 Is C 2 ~ C 6 Alkenyl, halo (C 2 ~ C 6 ) Alkenyl, C 2 ~ C 6 Alkynyl, halo (C 2 ~ C 6 ) Alkynyl, phenyl (C 1 ~ C 6 ) Represents alkyl or phenyl,
    f1, p1, p2 and t1 each independently represents an integer of 0 or 1,
    f2, r, r1, r2 and t2 each independently represent an integer of 0, 1 or 2;
    m, n, f3 and t3 each independently represent an integer of 0, 1, 2 or 3;
    f4 and t4 each independently represents an integer of 0, 1, 2, 3 or 4;
    f5 and t5 each independently represent an integer of 0, 1, 2, 3, 4 or 5;
    qa, qb, qf and qj each independently represent an integer of 1, 2, 3, 4 or 5;
    f6 represents an integer of 0, 1, 2, 3, 4, 5 or 6,
    f7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7,
    f8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8;
    f9 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9,
    f10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
    f11 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11,
    f12 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12. Or a salt thereof.
  2. 　Ｑは、酸素原子を表す請求項１記載のケトン化合物又はその塩。 Q is a ketone compound or a salt thereof according to claim 1, wherein Q represents an oxygen atom.
  3. 　Ｑは、ＮＯＲ７を表す請求項１記載のオキシム化合物又はその塩。 The oxime compound or a salt thereof according to claim 1, wherein Q represents NOR 7 .
  4. 　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル又はジ（Ｃ１～Ｃ６）アルキルアミノカルボニルを表し、
    　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルコキシカルボニル又はＣ１～Ｃ６アルキルカルボニルを表す請求項２記載のケトン化合物又はその塩。     R 8a , R 8b , R 9a and R 9b are each independently a hydrogen atom, a halogen atom, cyano, C 1 -C 6 alkyl, —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, —C (O) OH, C 1 to C 6 alkoxycarbonyl, C 1 to C 6 alkylcarbonyl, —C (O) NH 2 , C 1 to C Represents 6 alkylaminocarbonyl or di (C 1 -C 6 ) alkylaminocarbonyl,
    R 10 , R 11 and R 12 are each independently a hydrogen atom, a halogen atom, cyano, C 1 -C 6 alkyl, —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonyl or C 1- ketone compound or a salt thereof according to claim 2, wherein represents a C 6 alkylcarbonyl.
  5. 　Ｒ６は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ６ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７又はＤ２－３８を表す請求項４記載のケトン化合物又はその塩。 R 6 is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 6b (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 6b (C 3 The compound according to claim 4, which represents -C 8 ) cycloalkyl, phenyl, phenyl substituted with (Z j ) qj , D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38. A ketone compound or a salt thereof.
  6. 　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル又はＣ１～Ｃ６アルコキシカルボニルを表し、
    　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｚ５は、水素原子を表す請求項５記載のケトン化合物又はその塩。     R 8a , R 8b , R 9a and R 9b each independently represent a hydrogen atom, C 1 -C 6 alkyl or C 1 -C 6 alkoxycarbonyl,
    R 10 , R 11 and R 12 each independently represents a hydrogen atom or C 1 -C 6 alkyl;
    The ketone compound or a salt thereof according to claim 5 , wherein Z 5 represents a hydrogen atom.
  7. 　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ、－Ｃ（Ｏ）Ｒ２、－Ｐ（Ｏ）（ＯＲ３ｃ）２又は－Ｐ（Ｓ）（ＯＲ３ｃ）２を表し、
    　Ｒ１ａは、Ｃ１～Ｃ８アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５、Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１ｂ、Ｒ１ｃ、Ｒ１ｄ及びＲ１ｅは、各々独立してＣ１～Ｃ８アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５又はＤ２－５６を表し、
    　Ｒ３ａ、Ｒ３ｂ、Ｒ４ａ及びＲ４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ｇで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表す請求項６記載のケトン化合物又はその塩。     A is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —S (O) r2 R 1a , —C (O) OR 1b , —C (S) OR 1c , —C (O) SR 1d , —C (S) SR 1e , —C (O) R 2 , —P (O) (OR 3c ) 2 or -P (S) (OR 3c ) 2
    R 1a is optionally substituted with C 1 ~ C 8 alkyl, optionally substituted with R 5a (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, R 5a (C 3 ~ C 8 ) Cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z a ) qa , —N (R 4b ) R 3b , D2-1, D2-2, D2- 8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55, D2-56, D2-100 to D2-106 or D2-107,
    R 1b , R 1c , R 1d and R 1e are each independently C 1 -C 8 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5b , C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z b ) qb , D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55 or D2-56,
    R 3a , R 3b , R 4a and R 4b are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5g , C 3 -C 8 cyclo The ketone compound or a salt thereof according to claim 6, which represents alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl or phenyl substituted by (Z b ) qb .
  8. 　Ｂは、Ｂ－１を表し、
    　Ａは、水素原子を表し、
    　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
    　Ｒ８ａ、Ｒ９ａ、Ｒ１０、Ｒ１１及びＲ１２は、水素原子を表し、
    　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
    　Ｚ６は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｚ８は、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ４１は、Ｄ３－５８ａ又はＤ３－６０ｂを表し
    　Ｘ３は、ハロゲン原子、Ｃ１～Ｃ６アルキル又はハロ（Ｃ１～Ｃ６）アルキルを表し、ｔ５が２の整数を表すとき、各々のＸ３は互いに同一であっても又は互いに相異なってもよく、
    　ｎ及びｒは、０を表し、
    　ｍ及びｔ３は、１の整数を表し、
    　ｔ５は、１又は２の整数を表す請求項７記載のケトン化合物又はその塩。     B represents B-1,
    A represents a hydrogen atom,
    R 6 represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl,
    R 8a , R 9a , R 10 , R 11 and R 12 represent a hydrogen atom,
    Z 4 represents a halogen atom, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 6 alkoxy;
    Z 6 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl,
    Z 8 represents a hydrogen atom or C 1 -C 6 alkyl,
    R 41 represents D3-58a or D3-60b X 3 represents a halogen atom, C 1 -C 6 alkyl or halo (C 1 -C 6 ) alkyl, and when t5 represents an integer of 2, X 3 may be the same as or different from each other;
    n and r represent 0;
    m and t3 represent an integer of 1;
    The ketone compound or a salt thereof according to claim 7, wherein t5 represents an integer of 1 or 2.
  9. 　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルキルチオ、Ｃ１～Ｃ６アルキルスルフィニル、Ｃ１～Ｃ６アルキルスルホニル、－Ｃ（Ｏ）ＯＨ、Ｃ１～Ｃ６アルコキシカルボニル、Ｃ１～Ｃ６アルキルカルボニル、－Ｃ（Ｏ）ＮＨ２、Ｃ１～Ｃ６アルキルアミノカルボニル又はジ（Ｃ１～Ｃ６）アルキルアミノカルボニルを表し、
    　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子、ハロゲン原子、シアノ、Ｃ１～Ｃ６アルキル、－ＯＨ、Ｃ１～Ｃ６アルコキシ、Ｃ１～Ｃ６アルコキシカルボニル又はＣ１～Ｃ６アルキルカルボニルを表す請求項３記載のオキシム化合物又はその塩。     R 8a , R 8b , R 9a and R 9b are each independently a hydrogen atom, a halogen atom, cyano, C 1 -C 6 alkyl, —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 to C 6 alkylsulfinyl, C 1 to C 6 alkylsulfonyl, —C (O) OH, C 1 to C 6 alkoxycarbonyl, C 1 to C 6 alkylcarbonyl, —C (O) NH 2 , C 1 to C Represents 6 alkylaminocarbonyl or di (C 1 -C 6 ) alkylaminocarbonyl,
    R 10 , R 11 and R 12 are each independently a hydrogen atom, a halogen atom, cyano, C 1 -C 6 alkyl, —OH, C 1 -C 6 alkoxy, C 1 -C 6 alkoxycarbonyl or C 1- oxime compound or a salt thereof according to claim 3 wherein representing the C 6 alkylcarbonyl.
  10. 　Ｒ６は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ６ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ６ｂで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、フェニル、（Ｚｊ）ｑｊで置換されたフェニル、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７又はＤ２－３８を表し、
    　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルケニル、Ｃ２～Ｃ６アルキニル、Ｒ７ｂで任意に置換された（Ｃ２～Ｃ６）アルキニル、－Ｓ（Ｏ）ｒ１Ｒ１５ａ、－Ｃ（Ｏ）ＯＲ１５ｂ、－Ｃ（Ｓ）ＯＲ１５ｂ、－Ｃ（Ｏ）ＳＲ１５ｂ、－Ｃ（Ｓ）ＳＲ１５ｂ、－Ｃ（Ｏ）Ｒ１６、－Ｐ（Ｏ）（ＯＲ１７ｃ）２又は－Ｐ（Ｓ）（ＯＲ１７ｃ）２を表す請求項９記載のオキシム化合物又はその塩。     R 6 is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 6b (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, optionally substituted with R 6b (C 3 ~ C 8 ) cycloalkyl, phenyl, (Z j ) phenyl substituted with qj , D2-32, D2-33, D2-34, D2-36, D2-37 or D2-38;
    R 7 is a hydrogen atom, C 1 ~ C 6 alkyl, optionally substituted with R 7b (C 1 ~ C 6 ) alkyl, C 2 ~ C 6 alkenyl, optionally substituted with R 7b (C 2 ~ C 6 ) alkenyl, C 2 -C 6 alkynyl, (C 2 -C 6 ) alkynyl optionally substituted with R 7b , —S (O) r1 R 15a , —C (O) OR 15b , —C (S ) OR 15b , —C (O) SR 15b , —C (S) SR 15b , —C (O) R 16 , —P (O) (OR 17c ) 2 or —P (S) (OR 17c ) 2 The oxime compound according to claim 9 or a salt thereof.
  11. 　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、各々独立して水素原子、Ｃ１～Ｃ８アルキル又はＣ１～Ｃ６アルコキシカルボニルを表し、
    　Ｒ１０、Ｒ１１及びＲ１２は、各々独立して水素原子又はＣ１～Ｃ６アルキルを表を表し、
    　Ｚ５は、水素原子を表す請求項１０記載のオキシム化合物又はその塩。     R 8a , R 8b , R 9a and R 9b each independently represent a hydrogen atom, C 1 -C 8 alkyl or C 1 -C 6 alkoxycarbonyl,
    R 10 , R 11 and R 12 each independently represent a hydrogen atom or C 1 -C 6 alkyl,
    The oxime compound or a salt thereof according to claim 10, wherein Z 5 represents a hydrogen atom.
  12. 　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ、－Ｃ（Ｏ）Ｒ２、－Ｐ（Ｏ）（ＯＲ３ｃ）２又は－Ｐ（Ｓ）（ＯＲ３ｃ）２を表し、
    　Ｒ１ａは、Ｃ１～Ｃ８アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ａで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５、Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１ｂ、Ｒ１ｃ、Ｒ１ｄ及びＲ１ｅは、各々独立してＣ１～Ｃ８アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５又はＤ２－５６を表し、
    　Ｒ３ａ、Ｒ３ｂ、Ｒ４ａ及びＲ４ｂは、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ５ｇで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表し、
    　Ｒ１５ａは、Ｃ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ２０で任意に置換された（Ｃ３～Ｃ８）シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ１８）Ｒ１７、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５、Ｄ２－５６、Ｄ２－１００～Ｄ２－１０６又はＤ２－１０７を表し、
    　Ｒ１５ｂは、Ｃ１～Ｃ８アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル、（Ｚｂ）ｑｂで置換されたフェニル、Ｄ２－１、Ｄ２－２、Ｄ２－８、Ｄ２－３２、Ｄ２－３３、Ｄ２－３４、Ｄ２－３６、Ｄ２－３７、Ｄ２－３８、Ｄ２－５５又はＤ２－５６を表し、
    　Ｒ１７及びＲ１８は、各々独立して水素原子、Ｃ１～Ｃ６アルキル、Ｒ２０で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表す請求項１１記載のオキシム化合物又はその塩。     A is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —S (O) r2 R 1a , —C (O) OR 1b , —C (S) OR 1c , —C (O) SR 1d , —C (S) SR 1e , —C (O) R 2 , —P (O) (OR 3c ) 2 or -P (S) (OR 3c ) 2
    R 1a is optionally substituted with C 1 ~ C 8 alkyl, optionally substituted with R 5a (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, R 5a (C 3 ~ C 8 ) Cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z a ) qa , —N (R 4b ) R 3b , D2-1, D2-2, D2- 8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55, D2-56, D2-100 to D2-106 or D2-107,
    R 1b , R 1c , R 1d and R 1e are each independently C 1 -C 8 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5b , C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z b ) qb , D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55 or D2-56,
    R 3a , R 3b , R 4a and R 4b are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5g , C 3 -C 8 cyclo Represents alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl or phenyl substituted by (Z b ) qb ;
    R 15a is optionally substituted with C 1 ~ C 8 alkyl, optionally substituted with R 20 (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, R 20 (C 3 ~ C 8 ) Cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, phenyl substituted with (Z a ) qa , —N (R 18 ) R 17 , D2-1, D2-2, D2- 8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2-55, D2-56, D2-100 to D2-106 or D2-107,
    R 15b is C 1 -C 8 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, Phenyl, phenyl substituted with (Z b ) qb , D2-1, D2-2, D2-8, D2-32, D2-33, D2-34, D2-36, D2-37, D2-38, D2 -55 or D2-56,
    R 17 and R 18 are each independently a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 20 , C 3 -C 8 cycloalkyl, C 2 -C The oxime compound or a salt thereof according to claim 11, which represents 6- alkenyl, C 2 -C 6 alkynyl, phenyl or phenyl substituted by (Z b ) qb .
  13. 　Ｂは、Ｂ－１を表し、
    　Ａは、水素原子、Ｃ１～Ｃ６アルキル、Ｒ５で任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ２Ｒ１ａ、－Ｃ（Ｏ）ＯＲ１ｂ、－Ｃ（Ｓ）ＯＲ１ｃ、－Ｃ（Ｏ）ＳＲ１ｄ、－Ｃ（Ｓ）ＳＲ１ｅ又は－Ｃ（Ｏ）Ｒ２を表し、
    　Ｒ１ａは、Ｃ１～Ｃ６アルキル、Ｒ５ａで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、フェニル、（Ｚａ）ｑａで置換されたフェニル、－Ｎ（Ｒ４ｂ）Ｒ３ｂ又はＤ２－１０１を表し、
    　Ｒ１ｂは、Ｃ１～Ｃ６アルキル、Ｒ５ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ２～Ｃ６アルケニル、フェニル又は（Ｚｂ）ｑｂで置換されたフェニルを表し、
    　Ｒ１ｃは、フェニル又はＤ２－５６を表し、
    　Ｒ１ｄは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１ｅは、フェニルを表し、
    　Ｒ２は、Ｃ１～Ｃ６アルキル、Ｒ５ｆで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ３～Ｃ８シクロアルキル、Ｒ５ｆで任意に置換された（Ｃ３～Ｃ８）シクロアルキル、フェニル、（Ｚｆ）ｑｆで置換されたフェニル、キノリン－８－イル、－Ｎ（Ｒ４ａ）Ｒ３ａ、Ｄ２－１、Ｄ２－３４、Ｄ２－１００又はＤ２－１０２を表し、
    　Ｒ３ａ及びＲ４ａは、各々独立してＣ１～Ｃ６アルキルを表し、
    　Ｒ３ｂ及びＲ４ｂは、各々独立してＣ１～Ｃ６アルキルを表し、
    　Ｒ５は、－ＯＲ３１、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
    　Ｒ５ａは、ハロゲン原子を表し、
    　Ｒ５ｂは、ハロゲン原子、Ｃ１～Ｃ６アルコキシ又はフェニルを表し、
    　Ｒ５ｆは、ハロゲン原子、－ＯＲｆ、－Ｓ（Ｏ）ｒ２Ｒｆ、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
    　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
    　Ｒ７は、水素原子、Ｃ１～Ｃ６アルキル、Ｒ７ｂで任意に置換された（Ｃ１～Ｃ６）アルキル、Ｃ２～Ｃ６アルケニル、Ｃ２～Ｃ６アルキニル、－Ｓ（Ｏ）ｒ１Ｒ１５ａ、－Ｃ（Ｏ）ＯＲ１５ｂ又は－Ｃ（Ｏ）Ｒ１６を表し、
    　Ｒ７ｂは、ハロゲン原子、シアノ、Ｃ３～Ｃ８シクロアルキル、－ＯＲ３１ｂ、フェニル又は（Ｚｊ）ｑｊで置換されたフェニルを表し
    　Ｒ８ａ、Ｒ９ａ、Ｒ１０、Ｒ１１及びＲ１２は、水素原子を表し、
    　Ｒ１５ａは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１５ｂは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１６は、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又は－Ｎ（Ｒ１８）Ｒ１７を表し、
    　Ｒ１７は、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ１８は、水素原子を表し、
    　Ｒ３１は、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル、Ｃ１～Ｃ６アルコキシ（Ｃ１～Ｃ４）アルキル又は－Ｃ（Ｏ）Ｒ３７を表し、
    　Ｒ３１ｂは、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｒ３７は、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ、Ｃ３～Ｃ８シクロアルキルオキシ又はフェニルを表し、
    　Ｒｆは、Ｃ１～Ｃ６アルキル、フェニル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
    　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
    　Ｒ４１は、Ｄ３－３ａ、Ｄ３－１８ｂ、Ｄ３－２１ａ、Ｄ３－２１ｂ、Ｄ３－３３ａ、Ｄ３－５５ａ、Ｄ３－５５ｂ、Ｄ３－５７ａ、Ｄ３－５７ｂ、Ｄ３－５８ａ、Ｄ３－６０ａ又はＤ３－６０ｂを表し、
    　Ｚ６は、水素原子、ハロゲン原子又はＣ１～Ｃ６アルキルを表し、
    　Ｚ８は、水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｘ３は、ハロゲン原子、ニトロ、シアノ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルコキシカルボニルを表し、ｔ２、ｔ３、ｔ４又はｔ５が２以上の整数を表すとき、各々のＸ３は互いに同一であっても又は互いに相異なってもよく、
    　Ｚａは、ハロゲン原子、シアノ、ニトロ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ又はＣ１～Ｃ６アルキルカルボニルアミノを表し、ｑａが２以上の整数を表すとき、各々のＺａは互いに同一であっても又は互いに相異なってもよく、
    　Ｚｂは、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ１～Ｃ６アルコキシ又はＣ１～Ｃ６アルコキシカルボニルを表し、
    　Ｚｆは、ハロゲン原子、ニトロ、シアノ、Ｃ１～Ｃ６アルキル、ハロ（Ｃ１～Ｃ６）アルキル、Ｃ１～Ｃ６アルコキシ、ハロ（Ｃ１～Ｃ６）アルコキシ、Ｃ１～Ｃ６アルキルチオ又はＣ１～Ｃ６アルコキシカルボニルを表し、ｑｆが２以上の整数を表すとき、各々のＺｆは互いに同一であっても又は互いに相異なってもよく、
    　Ｚｊは、ハロゲン原子を表し、
    　ｆ３、ｆ４、ｆ７、ｆ８、ｆ１０、ｎ及びｐ２は、０を表し、
    　ｍ、ｑｂ、ｑｊ、ｔ２及びｔ４は、１の整数を表し、
    　ｔ５及びｒは、各々独立して０、１又は２の整数を表し、
    　ｔ３は、１又は２の整数を表す
    　ｑａ及びｑｆは、各々独立して１、２又は３の整数を表し、
    　ｒ１は、２の整数を表し、
    　ｒ２は、０又は２の整数を表す請求項１２記載のオキシム化合物又はその塩。     B represents B-1,
    A is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —S (O) r2 R 1a , -C (O) OR 1b , -C (S) OR 1c , -C (O) SR 1d , -C (S) SR 1e or -C (O) R 2
    R 1a is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 5a , C 3 -C 8 cycloalkyl, phenyl, phenyl substituted with (Z a ) qa ,- N (R 4b ) R 3b or D2-101,
    R 1b is C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkenyl, phenyl or (Z b ) qb optionally substituted with R 5b Represents phenyl substituted with
    R 1c represents phenyl or D2-56,
    R 1d represents C 1 -C 6 alkyl;
    R 1e represents phenyl,
    R 2 is alkyl, C 1 ~ C 6 substituted optionally substituted with R 5f (C 1 ~ C 6 ) alkyl, C 3 ~ C 8 cycloalkyl, optionally with R 5f (C 3 ~ C 8 ) Represents cycloalkyl, phenyl, phenyl substituted with (Z f ) qf , quinolin-8-yl, —N (R 4a ) R 3a , D2-1, D2-34, D2-100 or D2-102;
    R 3a and R 4a each independently represent C 1 -C 6 alkyl;
    R 3b and R 4b each independently represent C 1 -C 6 alkyl,
    R 5 represents —OR 31 , phenyl or phenyl substituted with (Z f ) qf ;
    R 5a represents a halogen atom,
    R 5b represents a halogen atom, C 1 -C 6 alkoxy or phenyl,
    R 5f represents a halogen atom, —OR f , —S (O) r2 R f , phenyl or phenyl substituted with (Z f ) qf ;
    R 6 represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl,
    R 7 is a hydrogen atom, C 1 -C 6 alkyl, (C 1 -C 6 ) alkyl optionally substituted with R 7b , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, —S (O) r1 represents R 15a, -C (O) oR 15b or -C (O) R 16,
    R 7b represents a halogen atom, cyano, C 3 -C 8 cycloalkyl, —OR 31b , phenyl or phenyl substituted with (Z j ) qj R 8a , R 9a , R 10 , R 11 and R 12 are Represents a hydrogen atom,
    R 15a represents C 1 -C 6 alkyl;
    R 15b represents C 1 -C 6 alkyl;
    R 16 represents C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or —N (R 18 ) R 17 ,
    R 17 represents C 1 -C 6 alkyl;
    R 18 represents a hydrogen atom,
    R 31 represents C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 6 alkoxy (C 1 -C 4 ) alkyl or —C (O) R 37 ,
    R 31b represents a hydrogen atom or C 1 -C 6 alkyl,
    R 37 represents C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 8 cycloalkyloxy or phenyl,
    R f is, C 1 ~ C 6 alkyl, represents phenyl substituted by phenyl or (Z f) qf,
    Z 4 represents a halogen atom, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 6 alkoxy;
    R 41 is, D3-3a, D3-18b, D3-21a, D3-21b , D3-33a, D3-55a, D3-55b, D3-57a, D3-57b, D3-58a, D3-60a or D3- 60b,
    Z 6 represents a hydrogen atom, a halogen atom or C 1 -C 6 alkyl,
    Z 8 represents a hydrogen atom or C 1 -C 6 alkyl,
    X 3 represents a halogen atom, nitro, cyano, C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl, t2, t3, t4 Or when t5 represents an integer of 2 or more, each X 3 may be the same as or different from each other;
    Z a is a halogen atom, cyano, nitro, C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, C 1 -C 6 alkoxy, halo (C 1 -C 6 ) alkoxy or C 1 -C 6 When alkylcarbonylamino is represented and qa represents an integer of 2 or more, each Z a may be the same as or different from each other,
    Z b represents a halogen atom, C 1 -C 6 alkyl, C 1 -C 6 alkoxy or C 1 -C 6 alkoxycarbonyl,
    Z f is a halogen atom, nitro, cyano, C 1 ~ C 6 alkyl, halo (C 1 ~ C 6) alkyl, C 1 ~ C 6 alkoxy, halo (C 1 ~ C 6) alkoxy, C 1 ~ C 6 Represents alkylthio or C 1 -C 6 alkoxycarbonyl, and when qf represents an integer of 2 or more, each Z f may be the same as or different from each other;
    Z j represents a halogen atom,
    f3, f4, f7, f8, f10, n and p2 represent 0;
    m, qb, qj, t2 and t4 represent an integer of 1;
    t5 and r each independently represents an integer of 0, 1 or 2;
    t3 represents an integer of 1 or 2 qa and qf each independently represents an integer of 1, 2 or 3,
    r1 represents an integer of 2;
    The oxime compound or a salt thereof according to claim 12, wherein r2 represents 0 or an integer of 2.
  14. 　Ｚ７は、－ＯＲ４１を表す請求項１３記載のオキシム化合物又はその塩。 The oxime compound or a salt thereof according to claim 13, wherein Z 7 represents -OR 41 .
  15. 　Ａは、水素原子、Ｃ１～Ｃ６アルキル又は－Ｃ（Ｏ）Ｒ２を表し、
    　Ｒ２は、Ｃ１～Ｃ６アルキル又は（Ｚｆ）ｑｆで置換されたフェニルを表し、
    　Ｒ６は、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ７は、Ｃ１～Ｃ６アルキルを表し、
    　Ｚ７は、－Ｓ（Ｏ）ｒＲ４１を表し、
    　Ｚ４は、Ｃ１～Ｃ６アルコキシを表し、
    　Ｒ４１は、Ｄ３－６０ｂを表し、
    　Ｚ６及びＺ８は、水素原子を表し、
    　Ｘ３は、ハロゲン原子を表し、
    　Ｚｆは、ハロゲン原子を表し、
    　ｑｆは、１又は２の整数を表し、
    　ｔ５は、１の整数を表す請求項１３記載のオキシム化合物又はその塩。     A represents a hydrogen atom, C 1 -C 6 alkyl or —C (O) R 2 ;
    R 2 represents phenyl substituted with C 1 -C 6 alkyl or (Z f ) qf ;
    R 6 represents C 1 -C 6 alkyl,
    R 7 represents C 1 -C 6 alkyl,
    Z 7 represents —S (O) r R 41 ,
    Z 4 represents C 1 -C 6 alkoxy,
    R 41 represents D3-60b;
    Z 6 and Z 8 represent a hydrogen atom,
    X 3 represents a halogen atom,
    Z f represents a halogen atom,
    qf represents an integer of 1 or 2,
    The oxime compound or a salt thereof according to claim 13, wherein t5 represents an integer of 1.
  16. 　式（３）：
    Figure JPOXMLDOC01-appb-C000006
     ［式中、Ｑは、ＮＯＲ７を表し、
    　Ａは、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ６は、Ｃ１～Ｃ６アルキル又はＣ３～Ｃ８シクロアルキルを表し、
    　Ｒ７は、Ｃ１～Ｃ６アルキルを表し、
    　Ｒ８ａ、Ｒ８ｂ、Ｒ９ａ及びＲ９ｂは、水素原子を表し、
    　Ｚ４は、ハロゲン原子、Ｃ１～Ｃ６アルキル、Ｃ３～Ｃ８シクロアルキル又はＣ１～Ｃ６アルコキシを表し、
    　Ｚ５は、水素原子を表し、
    　Ｚ６及びＺ８は、各々独立して水素原子又はＣ１～Ｃ６アルキルを表し、
    　Ｘ３ａは、Ｃ１～Ｃ６アルキルを表し、
    　ｍは、１の整数を表し、
    　ｎは、０の整数を表し、
    　ｔ４は、４の整数を表す］で表される請求項１乃至請求項１５のいずれか一項に記載の化合物の製造中間体。     Formula (3):
    Figure JPOXMLDOC01-appb-C000006
     [Wherein Q represents NOR 7 ;
    A represents C 1 -C 6 alkyl;
    R 6 represents C 1 -C 6 alkyl or C 3 -C 8 cycloalkyl,
    R 7 represents C 1 -C 6 alkyl,
    R 8a , R 8b , R 9a and R 9b represent a hydrogen atom,
    Z 4 represents a halogen atom, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl or C 1 -C 6 alkoxy,
    Z 5 represents a hydrogen atom,
    Z 6 and Z 8 each independently represent a hydrogen atom or C 1 -C 6 alkyl,
    X 3a represents C 1 -C 6 alkyl;
    m represents an integer of 1;
    n represents an integer of 0;
    The production intermediate of a compound according to any one of claims 1 to 15, wherein t4 represents an integer of 4.
  17. 　請求項１乃至請求項１５のいずれか一項に記載のケトン及びオキシム化合物並びにそれらの塩から選ばれる１種又は２種以上を有効成分として含有する農薬。 An agrochemical containing one or more selected from the ketone and oxime compounds according to any one of claims 1 to 15 and salts thereof as an active ingredient.
  18. 　請求項１乃至請求項１５のいずれか一項に記載のケトン及びオキシム化合物並びにそれらの塩から選ばれる１種又は２種以上を有効成分として含有する除草剤。 A herbicide containing, as an active ingredient, one or more selected from the ketone and oxime compounds according to any one of claims 1 to 15 and salts thereof.
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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05500520A (en) * 1990-03-30 1993-02-04 ダウエランコ Substituted cyclohexanedione and its herbicide use
JP2011526597A (en) * 2008-07-03 2011-10-13 シンジェンタ リミテッド 5-Heterocyclylalkyl-3-hydroxy-2-phenylcyclopent-2-enone as a herbicide
JP2012515742A (en) * 2009-01-22 2012-07-12 シンジェンタ リミテッド Cyclopentadione derivatized herbicide
WO2016062587A1 (en) * 2014-10-20 2016-04-28 Syngenta Participations Ag Herbicidal compounds
WO2016098899A1 (en) * 2014-12-18 2016-06-23 日産化学工業株式会社 Ketone or oxime compound, and herbicide
JP2017218444A (en) * 2016-06-07 2017-12-14 日産化学工業株式会社 Ketone or oxime compound and herbicide
WO2017217553A1 (en) * 2016-06-17 2017-12-21 日産化学工業株式会社 Oxime compound and herbicide

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05500520A (en) * 1990-03-30 1993-02-04 ダウエランコ Substituted cyclohexanedione and its herbicide use
JP2011526597A (en) * 2008-07-03 2011-10-13 シンジェンタ リミテッド 5-Heterocyclylalkyl-3-hydroxy-2-phenylcyclopent-2-enone as a herbicide
JP2012515742A (en) * 2009-01-22 2012-07-12 シンジェンタ リミテッド Cyclopentadione derivatized herbicide
WO2016062587A1 (en) * 2014-10-20 2016-04-28 Syngenta Participations Ag Herbicidal compounds
WO2016098899A1 (en) * 2014-12-18 2016-06-23 日産化学工業株式会社 Ketone or oxime compound, and herbicide
JP2017218444A (en) * 2016-06-07 2017-12-14 日産化学工業株式会社 Ketone or oxime compound and herbicide
WO2017217553A1 (en) * 2016-06-17 2017-12-21 日産化学工業株式会社 Oxime compound and herbicide

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