WO2018131690A1 - Composé de cétone ou d'oxime et herbicide - Google Patents

Composé de cétone ou d'oxime et 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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English (en)
Japanese (ja)
Inventor
沼田　昭
中村　俊之
有理 吉野
祐人 臼井
孝将 古橋
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日産化学工業株式会社
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Priority claimed from JP2017074726A external-priority patent/JP2020037515A/ja
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/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • C07—ORGANIC CHEMISTRY
    • 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
    • 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
    • C07D239/32—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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
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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 Table
    • 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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Le problème décrit par la présente invention est de fournir un nouveau produit agrochimique, particulièrement un nouvel herbicide. La solution selon l'invention porte sur un composé de cétone ou d'oxime représenté par la formule (1) et sur un herbicide contenant ce composé. (Dans la formule, B représente B-1 ou B-2 ; Q représente un atome d'oxygène ou NOR7 ; A représente un atome d'hydrogène ou similaire ; R6 représente un groupe alkyle en C1-C6 ou similaire ; R7 représente un groupe alkyle en C1-C6 ou similaire ; chacun de R8a et R9a représente un atome d'hydrogène ou un groupe alcoxycarbonyle en C1-C6 ; chacun de R8b et R9b représente un atome d'hydrogène ; Z4 représente un groupe alkyle en C1-C6 ou similaire ; Z7 représente -OR41 ; et R41 représente un noyau hétérocyclique tel que D3-18a.)
PCT/JP2018/000711 2017-01-13 2018-01-12 Composé de cétone ou d'oxime et herbicide WO2018131690A1 (fr)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05500520A (ja) * 1990-03-30 1993-02-04 ダウエランコ 置換シクロヘキサンジオン及びその除草剤用途
JP2011526597A (ja) * 2008-07-03 2011-10-13 シンジェンタ リミテッド 除草剤としての５−ヘテロシクリルアルキル−３−ヒドロキシ−２−フェニルシクロペント−２−エノン
JP2012515742A (ja) * 2009-01-22 2012-07-12 シンジェンタ リミテッド シクロペンタジオン誘導化除草剤
WO2016062587A1 (fr) * 2014-10-20 2016-04-28 Syngenta Participations Ag Composés herbicides
WO2016098899A1 (fr) * 2014-12-18 2016-06-23 日産化学工業株式会社 Cétone ou oxime, et herbicide
JP2017218444A (ja) * 2016-06-07 2017-12-14 日産化学工業株式会社 ケトン若しくはオキシム化合物及び除草剤
WO2017217553A1 (fr) * 2016-06-17 2017-12-21 日産化学工業株式会社 Composé d'oxime et herbicide

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05500520A (ja) * 1990-03-30 1993-02-04 ダウエランコ 置換シクロヘキサンジオン及びその除草剤用途
JP2011526597A (ja) * 2008-07-03 2011-10-13 シンジェンタ リミテッド 除草剤としての５−ヘテロシクリルアルキル−３−ヒドロキシ−２−フェニルシクロペント−２−エノン
JP2012515742A (ja) * 2009-01-22 2012-07-12 シンジェンタ リミテッド シクロペンタジオン誘導化除草剤
WO2016062587A1 (fr) * 2014-10-20 2016-04-28 Syngenta Participations Ag Composés herbicides
WO2016098899A1 (fr) * 2014-12-18 2016-06-23 日産化学工業株式会社 Cétone ou oxime, et herbicide
JP2017218444A (ja) * 2016-06-07 2017-12-14 日産化学工業株式会社 ケトン若しくはオキシム化合物及び除草剤
WO2017217553A1 (fr) * 2016-06-17 2017-12-21 日産化学工業株式会社 Composé d'oxime et herbicide

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