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WO2004052849A1 - Derive de benzoyle ayant un groupe sulfoximine et herbicide - Google Patents

Derive de benzoyle ayant un groupe sulfoximine et herbicide Download PDF

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WO2004052849A1
WO2004052849A1 PCT/JP2003/015843 JP0315843W WO2004052849A1 WO 2004052849 A1 WO2004052849 A1 WO 2004052849A1 JP 0315843 W JP0315843 W JP 0315843W WO 2004052849 A1 WO2004052849 A1 WO 2004052849A1
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group
s02me
alkoxy
alkyl
substituted
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PCT/JP2003/015843
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English (en)
Japanese (ja)
Inventor
Satoshi Kajita
Hideaki Ohmura
Masaya Akashi
Shuichi Kojima
Atsushi Satoh
Kazuyuki Tomida
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Nippon Soda Co.,Ltd.
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Priority to JP2005502371A priority Critical patent/JP4471928B2/ja
Priority to AU2003289322A priority patent/AU2003289322A1/en
Publication of WO2004052849A1 publication Critical patent/WO2004052849A1/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
    • A01N43/72—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
    • A01N43/80—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 1,2
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/08—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 oxygen 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
    • A01N43/02—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
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    • 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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-membered rings with oxygen 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
    • A01N43/02—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
    • A01N43/14—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 six-membered rings
    • A01N43/18—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 six-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
    • A01N43/02—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
    • A01N43/20—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 three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/22—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 rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/26—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 two or more hetero atoms five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—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
    • A01N43/24—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 two or more hetero atoms
    • A01N43/32—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 two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones

Definitions

  • the present invention relates to a benzoylvirazole derivative compound having a sulfoximine group or a salt thereof.
  • the present invention relates to a herbicide containing one or more kinds as an active ingredient.
  • Background technology :
  • Patent Document 1
  • Patent Document 2
  • An object of the present invention is to provide a herbicide which can be synthesized industrially advantageously, has a low dose, is effective, has high safety, and has high crop selectivity.
  • Q represents an organic group selected from the groups represented by the following formulas Q 1 to Q 6;
  • R1 is a hydrogen atom, a halogen atom, Ci-3 alkyl group, d 3 haloalkyl group, Ci 3 alkoxy group, flicking 3 haloalkoxy group, a nitro group, Shiano group, or the formula: represents a SOnR16
  • R 2 and R 3 are each independently a C 6 alkyl group, (Ci-3 alkyl group, ⁇ alkoxy group, may be substituted with halogen, etc.) C 3 __ 6 cycloalkyl, C 2 6 alkenyl group, flicking 6 haloalkyl group, CI- 6 alkoxy d-6 alkyl group, - 6 haloalkoxy
  • Ci 6 Represents an alkyl group, a phenyl group optionally substituted with J, or a heterocyclic ring optionally substituted with J, or is substituted with J by linking R 2 and R 3 May form a 3- to 8-membered heterocyclic ring containing 1-4 nitrogen atoms, oxygen atoms, or sulfur atoms, and R4 is a hydrogen atom, a halogen atom, a C ⁇ 3 alkyl group, a C ⁇ 3 haloalkyl groups, C ⁇ 3 al Coxy group, d-3 haloalkoxy
  • R 5 represents a hydrogen atom, a halogen atom, or a Ci-3 alkyl group
  • R 6 is a hydrogen atom, d 6 alkyl group, Ci-6 haloalkyl group, phenyl group optionally substituted with J, benzoyl group optionally substituted with J, C-6 alkylsulfonyl group, substituted with J
  • benzenesulfonyl group naphthyl group optionally substituted with J
  • benzyl group optionally substituted with J
  • naphthylmethyl group optionally substituted with J
  • substituted with J Represents a benzoylmethyl group which may benzoylmethyl group which may benzoylmethyl group which may benzoylmethyl group which may benzoylmethyl group which may benzoylmethyl group which may benzoylmethyl group which may be
  • R 7 is a hydrogen atom, Ci 6 alkyl, (C ⁇ 3 alkyl group, - 3 alkoxy group, substituted with a halogen or the like may be) C 3 6 cycloalkyl group, a haloalkyl group, C 2 - 6 alkenyl group Or represents a C 26 alkynyl group,
  • R 8 is a hydrogen atom, CI- 6 alkyl group, (CI- 3 alkyl group, d 3 alkoxy group, may be substituted with halogen, etc.) C 3 _ 6 cycloalkyl group, d-6 haloalkyl group, or formula:
  • R9 is C i-6 alkyl group, (Ci-3 alkyl group, - 3 alkoxy group, may be substituted with halogen, etc.) C 3 6 cycloalkyl group, Ci 6 haloalkyl group, C 2 _ 6 alkenyl group , C 2
  • R 1 0 and R 1 1 are each independently a hydrogen atom, CI_ 6 alkyl group, (d-3 alkyl group, CL 3 alkoxy group, may be substituted with halogen, etc.) C 3 _ 6 cycloalkyl group , C haloalkyl group, C 2 6 alkenyl, C 2 6 alkynyl group, CI- 6 alkoxy Ci 6 Al kill group, hydroxy group, alkoxy group, or represent a C i-6 haloalkoxy group, were or, R 10 and R 11 may be combined with a nitrogen atom to form a 4- to 8-membered heterocyclic ring containing 1 to 4 nitrogen, oxygen, or sulfur atoms,
  • R 12 and R 13 are each independently a hydrogen atom, a C i 6 alkyl group, (optionally substituted with a d_ 3 alkyl group, a Ci 3 alkoxy group, a halogen, etc.) C 3 _ 6 cycloalkyl group , C i 6 haloalkyl group, C 2 6 alkenyl, C 2 _ 6 alkynyl, C i-6 alkoxy flicking 6 Al kill group, C -6 alkoxy group, flicking 6 haloalkoxy group, optionally substituted with J A good phenyl group or the formula:
  • C OR 19
  • R 14 is a hydrogen atom, CI- 6 alkyl group, a cycloalkyl group of C 3 _ 6, Haroaruki Le group of d, alkoxy group flicking 6, a haloalkoxy group C 6 or,, d-6 alkoxy CI- 6 Represents an alkyl group,
  • R15 is hydrogen, CI- 6 alkyl group, a cycloalkyl group of C 3 _ 6, Haroaruki Le group d 6, d-6 alkoxy group, CI- 6 haloalkoxy group, - 6 alkoxy
  • Ci-6 alkyl Represents a group, a halogen atom, an alkoxycarbonyl group, or a cyano group,
  • R 16 is a hydrogen atom, a CL 6 alkyl group, (which may be substituted with a C! _ 3 alkyl group, — 3 alkoxy group, halogen, etc.) C 3 _ 6 cycloalkyl group, d 6 haloalkyl group, C 2 _ 6 an alkenyl group, C 2 _ 6 alkynyl, Ci-6 alkoxy group or, to display the CI- 6 haloalkoxy group,
  • R17 is hydrogen, CI- 6 alkyl group, (CI- 3 alkyl group, Ci 3 alkoxy group, may be substituted with halogen, etc.) C 3 _ 6 cycloalkyl group, CI_ 6 haloalkyl group, C 2 6 an alkenyl group, C 2 6 alkynyl group, CL-6 alkoxy group or, an haloalkoxy group to table,
  • R 18 is a hydrogen atom, d 6 alkyl group, (which may be substituted by Ci-3 alkyl group, —3 alkoxy group, halogen, etc.) C 3 _ 6 cycloalkyl group, Ci-6 haloalkyl group, C 2 _ 6 alkenyl group, C 2 _ 6 alkynyl group, Ci-6 alkoxy group, haloalkoxy group, or a phenoxy group which may be substituted with J,
  • R 19 is a hydrogen atom, Ci 6 alkyl group, - 3 alkyl group, Ci-3 alkoxy group, may be substituted with halogen, etc.) C 3 _ 6 cycloalkyl group, CI- 6 haloalkyl group, C 2 _ 6 alkenyl group, C 2 _ 6 alkynyl group, Ci-6 alkoxy group, d-6 haloalkoxy group, or a phenoxy group which may be substituted with J,
  • n an integer of 0, 1 or 2
  • n 0 or an integer of 1 to 4,
  • G represents an oxygen atom or a sulfur atom
  • J is C ⁇ 3 alkyl group, Ci-3 haloalkyl group, C -! 3 alkoxy group, hydroxy group, nitro port group, Shiano group, an amino group, d_ 6 alkoxycarbonyl group, a halogen atom or,, d_ 3 ⁇ J Les Represents a killsulfonyl group,
  • X represents the formula: CR20R21, the formula: NR20, or represents an oxygen atom
  • Y is Okiso group
  • Ci-6 alkyl group (C i-3 alkyl group, d 3 alkoxy group, substituted with a halogen or the like may be)
  • C 3 _ 6 cycloalkyl group (CL 6 haloalkyl group, C 2 _ 6 alkenyl Le group, C 2 _ 6 alkynyl, C ⁇ 6 alkoxy.
  • 6 represents an alkyl group, a C! -6 alkoxy group, a d-6 haloalkoxy group, or a phenyl group which may be substituted by J.
  • Y When m is 2 or more, Y may be different, Furthermore Y when m is 2 or more, a nitrogen atom, an oxygen atom, or the following formula becomes C Bok 6 alkylene chain comprising three 0 sulfur atom: 3-8 membered scan shown in Q 2-1 A pyro ring, a 3- to 8-membered condensed ring represented by the following formula: Q2-2, or a 3- to 8-membered bridged ring represented by the following formula: Q2-3 may be formed,
  • R 20 is hydrogen atom, C ⁇ e alkyl group, (E group, - 3 alkoxy group, may be substituted with halo gen, etc.) C 3 6 cycloalkyl group, CI- 6 haloalkyl group, hydroxy sheet group , alkoxy groups, C 6 haloalkoxy group, Ci 6 alkoxy Cal Poni group, or, Ji represents Bok 3 alkyl sulfonyl group,
  • R 2 1 is hydrogen atom, C i 6 alkyl group, (C i-3 alkyl group, Ci 3 alkoxy group, may be substituted with halo gen, etc.) C 3 6 cycloalkyl group, Ci-6 haloalkyl group , Ci 6 alkoxy, C i-6 haloalkoxy, C-6 alkoxycarbonyl, or cyano. ]
  • a herbicide comprising, as an active ingredient, one or more of a benzoic acid compound represented by or a salt thereof.
  • R 1 is a hydrogen atom; a halogen atom such as fluorine, chlorine, bromine, or iodine; a 3-alkyl group such as methyl, ethyl, n-propyl, or isopropyl; chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl C ⁇ 3 haloalkyl groups such as trichloromethyl, trichloromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl; methoxy, ethoxy, n-propoxy, isopropoxy, etc.
  • a halogen atom such as fluorine, chlorine, bromine, or iodine
  • a 3-alkyl group such as methyl, ethyl, n-propyl, or isopropyl
  • R 2 and R 3 are each independently a Ci- 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl; cyclopropyl, 1-methyl cyclopropyl, 2-methylcyclopropyl, 2, 2-dimethyl-cyclopropyl propyl, 2 - chloro-cyclopropyl, 2, 2 - 6 cycloalkyl group - dichloro cyclopropyl, cyclobutyl, consequent opening pentyl, C 3 of cyclohexyl like cyclohexane Ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl , 3-pentenyl, 4-pentenyl, 1-methyl
  • a heterocyclic ring such as pyrazine; or R 2 and R 3 are taken together (optionally substituted with J), thiophene, tetrahydrothiophene, thiopyran, tetrahydrorothiopyran, 4-oxochian Thiomorpholine, 1,4-dithiane, tetrahydrothiopyran_4-one, etc., may form a 3-8 membered heterocycle containing 1-4 nitrogen atoms, oxygen atoms, or sulfur atoms.
  • R4 is a hydrogen atom; a halogen atom such as fluorine, chlorine, bromine, and iodine; a Ci-3 alkyl group such as methyl, ethyl, n-propyl, and isopropyl; chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, and dibromomethyl.
  • D- 3 haloalkyl groups such as trichloromethyl, trifluoromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl; methoxy, ethoxy, n-propoxy, isopropoxy, etc.
  • R5 represents a hydrogen atom; a halogen atom such as fluorine, chlorine, bromine and iodine; or a Ci-3 alkyl group such as methyl, ethyl, n-propyl and isopropyl.
  • R6 is hydrogen; methyl, Echiru, n-propyl, isopropyl, n- butyl, sec- heptyl, isobutyl, C WINCH 6 alkyl group such as t- butyl; chloromethyl, Furuoromechiru, blanking Romomechiru, dichloromethyl, Jifuruoromechiru, dibromo Ci-ehaloalkyl groups such as methyl, trichloromethyl, trifluoromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, and benzoylfluoroethyl; phenyl optionally substituted with J A benzoyl group which may be substituted with J; a Ci-6 alkylsulfonyl group such as methanesulfonyl and ethanesulfonyl; a benzenesulfonyl group which may be substituted with J; a naphthyl group which
  • R 7 is a hydrogen atom; d-6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl; cyclopropyl, 1-methylcyclo Propyl, 2-methylcyclopropyl, 2, 2-dimethyl-cyclopropyl, 2-Metokishi black-propyl, 2-chloro-cyclopropyl, 2, 2-dichloro-cyclopropyl, Shikuropuchi Le, cyclopentyl, C 3 of cyclohexyl etc.
  • Cycloalkyl group cyclohexane - 6 Cycloalkyl group; chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, pentaful D- 6 haloalkyl groups such as ethorethyl; ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl,
  • cyclohexenyl 5 - 6 alkenyl group in addition, Echiniru, 1-propynyl, 2-propynyl, 1 Buchiniru, 2-heptynyl, 3-Bed ethynyl, 1-Methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-
  • 3-pentynyl, hexynyl to 1, 1, 1-dimethyl - represents a 2-C 2 _ 6 alkynyl group butynyl.
  • R8 is a hydrogen atom; C alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl; cyclopropyl, 1-methylcyclopropyl, 2-methoxycyclopropyl, 2-methoxycyclopropyl methylcyclopropyl, 2, 2-Jimechirushi black-propyl, 2-chloro-cyclopropyl, 2, 2-dichloro-cyclopropyl, Shikuropuchi Le, cyclopentyl, C 3 _ 6 cycloalkyl group cyclohexyl, etc.
  • R 9 is methyl, Echiru, n-propyl, isopropyl, n- butyl, sec- butyl, I Sobuchiru, such as t- butyl C, - 6 alkyl group; cyclopropyl, 1-methylstyrene cyclopropyl, 2-methylcyclopropyl , 2,2-dimethylcyclopropyl, 1-methoxycyclopropyl, 2-methoxycyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. of .
  • R 10 and R 11 are each independently a hydrogen atom; a C! -6 alkyl group such as methyl, ethyl, n_propyl, isopropyl, n-butyl, sec-butyl, isoptyl and 1: -butyl; Cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2-methoxycyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, cyclobutyl, cyclopentyl And cycloalkyl groups such as cyclohexyl; chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, 2,2,2-trichloromethyl, 2,2,2- Ci- 6 haloalkyl groups such as trifluoroethyl, pendufluorethy
  • R 12 and R 13 are each independently a hydrogen atom; methyl !, ethyl, n-propyl, isopropyl, n-butyl, sec-butylyl, isoptyl, t-butyl and the like!
  • _ 6 alkyl group cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2-methoxycyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2, 2-dichloro-cyclopropyl, cyclobutyl, cyclopentyl, C of hexyl, etc., to a consequent opening 3 - 6 cycloalkyl group; chloromethyl, Furuoromechiru, Promo methyl, di-chloromethyl, Jifuruoromechiru, dibromomethyl, trichloromethyl, Torifuruoromechi Le, 2, 2 Ci-6 haloalkyl groups such as 2,2-trichloroethyl, 2,2,2-trifluoroethyl and pennofluorethyl; ethenyl, 1-probenyl, 2-propenyl, 1-pthenyl, 2- Buten
  • Ci-6 alkoxyalkyl groups such as, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy, etc.
  • R 14 is a hydrogen atom; d- 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n_butyl, sec-butyl, isobutyl, t-butyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • Ci- 6 alkoxy groups; 2,2-difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro C haloalkoxy groups such as mouth ethoxy; methoxymethyl, ethoxymethyl, Tokishechiru represents Ci-e alkoxy C ⁇ e alkyl groups such as Etokishechi Le,
  • R 15 is a hydrogen atom; an alkyl group of Ci-6 such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • D-6 haloalkyl group such as methoxy, ethoxy, n-propoxy, isopropoxy; 2,2-difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2 —Ci-6 haloalkoxy groups such as ethoxy; methoxymethyl, ethoxymethyl, methoxy Kishechiru, Ci-s alkoxy CI- 6 alkyl groups such as Etokishechi Le; CI_ 6 alkoxycarbonyl two Le groups such as meth alkoxycarbonyl, ethoxycarbonyl, t _ butoxide deer Lupo sulfonyl; fluorine, chlorine, bromine, halogen atom and iodine Shiano Represents a group,
  • R 16 is a hydrogen atom; an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and t-butyl; cyclopropyl, 1-methylcycl C such as mouth propyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2-methoxycyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and t-butyl
  • cyclopropyl, 1-methylcycl C such as mouth propyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl,
  • R 17 is a hydrogen atom; Ci- 6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl; cyclopropyl, 1-methylcyclopropyl, 2- methylcyclopropyl, 2, 2-dimethyl-cyclopropyl, 2-Kuroroshi black-propyl, 2, 2-dichloro-cyclopropyl, Shikuropuchiru, cyclopentyl, C 3 of cyclohexyl etc.
  • cyclohexane - 6 cycloalkyl group chloromethyl, Furuoromechiru, bromomethyl, D- 6 haloalkyl groups such as dimethoxymethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, pennofluorethyl, etc .; ethenyl, 1-probenyl, 2-probenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2— Methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl , C 2 of cyclohexenyl, etc.,
  • the C 2 - 6 alkynyl group methoxy, ethoxy, n- propoxy, isopropoxy, n- butoxy, sec- butoxy, isobutoxy, C i one butoxy t - 6 alkoxy group; or, chloromethoxy, Jikurorome Bok alkoxy 6-haloalkoxy groups such as, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, and 1,1-difluoroethoxy; It is.
  • R 18 is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, sec
  • —Ci-6 alkyl groups such as butyl, isoptyl and t-butyl; cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2-methoxycyclopropyl, 2- chlorocyclopropyl, 2, 2-dichloro-cyclopropyl, Shikurobu chill, cyclopentyl, C 3 _ 6 cycloalkyl group cyclohexyl, etc.
  • cyclohexylene cyclohexylene; haloalkyl group, Eparu, 1 Purobe alkenyl, 2-propenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl - 2 - butenyl, 2-methyl-2 - butenyl, cyclohexenyl 1, cyclohexenyl 2, to 3-hexenyl, 4 one hexenyl, C 2 _ 6 alkenyl, such as cyclohexenyl 5- Ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-penty
  • R 19 is a hydrogen atom; C ⁇ s alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isoptyl, t-butyl; cyclopropyl, 1-methylcyclyl Mouth propyl, 2-methylcyclopropyl, 2, 2-dimethyl-cyclopropyl, 2-methoxy-cyclopropyl, 2-chloro-cyclopropyl, 2, 2-dichloro-cyclopropyl, Shikurobu chill, cyclopentyl, C 3 _ of cyclohexyl like cyclohexane 6- cycloalkyl group; d-6 haloalkyl group, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl — 2 —propenyl, 1-penten
  • Ci-6 haloalkoxy group such as methoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy; or J A phenoxy group;
  • n an integer of 0, 1 or 2.
  • n 0 or an integer of 1 to 4.
  • G represents an oxygen atom or a sulfur atom.
  • J is an alkyl group such as methyl, ethyl, n-propyl, isopropyl, etc .; chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, 2,2,2- C ⁇ 3 haloalkyl groups such as trichloroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl; alkoxy groups such as methoxy, ethoxy, n-propoxy and isopropoxy; hydroxy groups; nitro groups An alkoxy group such as methoxycarbonyl, ethoxycarbonyl, n-propoxyl-proponyl, isopropoxyl-proponyl, n-butoxycarbonyl or t-butoxycarbonyl; a halogen such as fluorine, chlorine, bromine or iodine; Atom; or methylsulf
  • Y is an oxo group
  • Ci-6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl
  • cyclopropyl 1-methylcyclopropyl, 2-methyl Cyclopropyl, 2,2-dimethylcyclopropyl, 1-methoxycyclopropyl, 2-methoxycyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • C 3 _ 6 cycloalkyl group chloromethyl, Furuoromechiru, Promo methyl, Jikurorome chill, Jifuruoromechiru, dibromomethyl, trichloromethyl, triflumizole Ruo Russia methyl, 2, 2, 2-trichloromethyl E chill, 2, 2, 2-triflate C ⁇ e haloalkyl groups such as oloethyl and pentafluoroethyl Ethenyl, 1-propenyl, 2-probenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl_2-propenyl, 1-pentenyl , 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, C 2 _ 6 alkenyl groups such as 5-he
  • C 2 _ 6 alkynyl group methoxy Alkoxy-6-alkyl groups such as methyl, methoxyethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t —Butoxy and the like — 6 alkoxy group; chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy and the like, and an alkoxy group; or J may be substituted.
  • methoxy Alkoxy-6-alkyl groups such as methyl, methoxyethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy
  • the following formula: 3 to 8 membered spiro ring shown in Q2-1, the following formula: 3 to 8 membered condensed ring shown in Q2-2, or Formula: may form a 3-8 membered bridged ring shown in Q 2-3 represents an.
  • R20 is a hydrogen atom; C ⁇ e alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl; cyclopropyl, 1-methylcyclopropyl, 2-methylcyclo propyl, 2, 2-dimethyl-cyclopropyl, 2-methoxyethanol cyclopropyl, 2-chloro-cyclopropyl, 2, 2-dichloro-cyclopropyl, cyclobutyl, cyclopentyl, C 3 _ 6 cycloalkyl group cyclohexyl, etc.
  • C ⁇ e alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl
  • cyclopropyl 1-methylcyclopropyl, 2-methylcycl
  • Mouth alkyl group hydroxy group; methoxy, ethoxy, n-propoxy D- 6 alkoxy groups such as, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy; chloromethoxy, dichloromethoxy, trichloro mouth methoxy, trifluoromethoxy, 1-fluoroethoxy, 1 1-difluoromethyl O b 6 haloalkoxy group ethoxy; methoxy Cal Poni Le, ethoxy Cal Poni le, n- Puropokishikaru d_ 6 alkoxycarbonyl group such Poniru; or, methylsulfonyl, Echirusuruhoniru, C i such n one propylsulfonyl _ 6 represents an alkylsulfonyl group.
  • R21 is a hydrogen atom; d-6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl; cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl propyl, 2, 2-dimethyl-cyclopropyl, 2-methoxyethanol cyclopropyl, 2-chloro-cyclopropyl, 2, 2-dichloro-cyclopropyl, cyclo heptyl, cyclopentyl, C 3 _ 6 cycloalkyl group cyclohexyl, etc.
  • d-6 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl
  • cyclopropyl 1-methylcyclopropyl, 2-methyl
  • chloro D- 6 such as methyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, pendufluorethyl, etc.
  • Haloalkyl group methoxy, ethoxy, n-propoxy, isopro D-6 alkoxy groups such as boxy, n-butoxy, sec-butoxy, isobutoxy, and t-butoxy; chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluo C ⁇ 6 haloal such as oloethoxy Represents a coxy group.
  • the compound of the present invention can be produced, for example, by the method shown in the following steps 1 to 7, but the compound of the present invention can also be synthesized by a generally known method, and is not limited to this method. .
  • Q of the compound of the present invention is represented by Q1, Q2 or Q6, R6 is a hydrogen atom and G is an oxygen atom, it can be produced, for example, by the methods shown in the following steps 1-3.
  • T represents a leaving group such as a chlorine atom or an imidazolyl group.
  • Compound I_Qla, I-Q2a and compound I_Q6a are obtained by converting a benzoic acid compound represented by the formula [IE] to a halogenating agent such as thionyl chloride or oxalyl chloride, or a carbonyl diimidazole.
  • a halogenating agent such as thionyl chloride or oxalyl chloride, or a carbonyl diimidazole.
  • a base such as triethylamine, pyridine, and benzene, toluene
  • a catalytic amount such as acetone cyanohydrin, lithium cyanide, sodium cyanide, etc. It can be produced by reacting o: to 12 in an organic solvent such as methylene chloride, chloroform, carbon tetrachlor
  • a compound in which R 6 is a group other than a hydrogen atom and G is an oxygen atom can be produced by the method shown in Step 2.
  • R6 ′ represents R6 excluding a hydrogen atom
  • W is halogen such as fluorine, chlorine, bromine, etc. Atom; or a leaving group such as methanesulfoxy, p-toluenesulfoxy, trifluoromethanesulfoxy, acetyloxy, benzoyloxy, etc.
  • the compound represented by the formula [I-Q1a], [I-Q2a] or the formula [I-Q6a] is converted to dimethylformamide (hereinafter abbreviated as DMF), tetrahydrofuran (hereinafter abbreviated as THF)
  • DMF dimethylformamide
  • THF tetrahydrofuran
  • a compound in which R 6 is a group other than a hydrogen atom and G is a sulfur atom can be produced by the method shown in Step 3.
  • R1 to R5, R6 ', R7, R8, R14, R15, W, Y and m have the same meaning as described above.
  • the compound represented by the formula [I-Qla], [I-Q2a] or the formula [I-Q6a] is converted to a sulfonic acid compound such as trifluoromethanesulfonate anhydride or trifluoromethanesulfonic anhydride.
  • the compound represented by the formula [Q3a] or [Q4a] is converted to a compound represented by the formula: in the presence of a base such as sodium hydride, potassium hydride, potassium t-butoxide, magnesium ethylate, triethylamine, potassium carbonate, or the like.
  • a base such as sodium hydride, potassium hydride, potassium t-butoxide, magnesium ethylate, triethylamine, potassium carbonate, or the like.
  • an organic solvent such as THF, getyl ether, DMF, methylene chloride, chloroform, acetonitrile, benzene, toluene, etc. at a rate of 50 to 120.
  • the compound represented by [I-Q4a] or the formula [I-Q4a] can be produced.
  • Step 5 When Q is a group represented by Q5 and G is an oxygen atom, it can be produced by the method represented by Step 5.
  • R22 represents an alkyl group such as methyl, ethyl, n-propyl, isopropyl, or t-butyl; a benzyl group; a phenyl group represented by R23 Is a hydrogen atom; an alkoxy group such as methoxy, ethoxy, n-propoxy, etc .; an amino group such as amino, dimethylamino, getylamino, R 24 is a hydrogen atom; an alkoxy group such as methoxy, ethoxy, n-propoxy, etc .; Represents an amino group such as getylamino.
  • the obtained compound represented by the formula [VI] is converted into a catalytic amount of an organic acid such as p_toluenesulfonic acid, methanesulfonic acid, acetic acid, or a catalyst.
  • an organic acid such as p_toluenesulfonic acid, methanesulfonic acid, acetic acid, or a catalyst.
  • an inorganic acid such as sulfuric acid or hydrochloric acid
  • an organic solvent such as benzene, toluene, THF, 1,4-dioxane, DMF, ethanol, methanol, or a mixed solvent of these organic solvents and water.
  • a decarboxylation reaction is performed at 120 and expressed by the formula [W] And compounds.
  • the compound represented by the formula [W] is combined with 1 to 3 equivalents of trialkyl orthoacetates such as trimethyl orthoacetate and triethylorthoacetate, N, N-dimethylacetamide dimethyl acetal, and the like.
  • trialkyl orthoacetates such as trimethyl orthoacetate and triethylorthoacetate, N, N-dimethylacetamide dimethyl acetal, and the like.
  • a solvent or an organic solvent such as benzene, toluene, THF, 1,4-dioxane, methylene chloride, chloroform, carbon tetrachloride, and acetonitrile at 0T: up to 120 ° C, the compound represented by the formula is obtained.
  • Step 6 When Q is a group represented by Q5 and G is a sulfur atom, it can be produced by the method represented by Step 6. Step 6:
  • compound [I-Q5b] can be produced by reacting compound ⁇ at a temperature of from 78 t to room temperature.
  • the starting compound [ ⁇ ] was prepared from benzoate ester [IX] and sulfoximine [X] according to the reaction conditions described in the literature (eg, Synthesis Volume 7, p. 911- 913, 2000) and then hydrolyze under general hydrolysis conditions (for example, caustic soda water).
  • R 1 to R 5 and W represent the same meaning as described above, and R 25 is an alkyl group; d_, Haloalkyl group; or alkyl group, d- 6 haloalkyl group, Ci-3 alkoxy group,
  • 3 represents a phenyl group which may be substituted with an alkylthio group, ⁇ alkylsulfonyl group, nitro group, cyano group, halogen atom or the like.
  • the benzoate ester [K] can be prepared by a known method (for example, disclosed in Japanese Patent Publications Nos. 05-039259, 04-501726, 02-006426, 02-006426, 64-052759, US 5092919, J. Med. Chem. , 1972, Vol. 15, No. 6, pp. 684, etc., as well as general methods (eg, 0 r ganic Synthesis, collectivevo 1 ume 5, p. 412, Organic Syn. t sis, colecti ve vo 1 ume 5, p. 142, Organic Synthesis, vol. 79, p. 43).
  • Compound [X] can be synthesized by a known method (for example, Synthes, 2000, Vol. 1, pp.!-64).
  • the compound [I] of the present invention may have optical isomers, and may also have many tautomers. All such isomers are included within the scope of the present invention.
  • the salts of the compound [I] of the present invention include metal salts such as lithium, sodium, potassium, calcium, magnesium, iron and copper; amines such as ammonia, triethylamine and triptylamine; bases such as pyridine and hydrazine. And the like.
  • the structure of the compound of the present invention was determined by NMR, IR, MS and the like.
  • CH2 CHCH2 0 ⁇ CH2
  • CH2 CHCH2 0 5-Me CH2
  • PhCH2C 0 0 5-Me CH2

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  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
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  • Plural Heterocyclic Compounds (AREA)
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Abstract

L'invention concerne un composé d'acide benzoique représenté par la formule [I] (dans laquelle Q représente un groupe sélectionné entre les groupes suivants : Q1, Q2, Q3, Q4, Q5, Q6, R1 ainsi que R4 à R15 représentent chacun hydrogène, alkyle, etc. ; R2 et R 3 représentent chacun alkyle ou un hétérocycle, ou R2 et R3 en association forment un hétérocycle, etc. ; G représente oxygène, etc. ; et X représente NR, CHR, oxygène, etc.) ou bien un sel du composé. L'invention concerne également un herbicide contenant le composé ou le sel. Le composé présente une excellente activité herbicide et par conséquent une composition contenant ledit composé est utile en tant qu'herbicide.
PCT/JP2003/015843 2002-12-12 2003-12-11 Derive de benzoyle ayant un groupe sulfoximine et herbicide WO2004052849A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006037945A1 (fr) * 2004-10-05 2006-04-13 Syngenta Limited Derives d’isoxazoline et leur utilisation comme herbicides
WO2008035737A1 (fr) * 2006-09-21 2008-03-27 Nippon Soda Co., Ltd. Dérivé de 4-nitrobenzoyle possédant un groupe sulfoxyimino et herbicide pour plante de riz
WO2009116290A1 (fr) * 2008-03-19 2009-09-24 日本曹達株式会社 Dérivés de 4-halogénobenzoyle ayant un groupe sulfoxyimino et herbicides
WO2010016230A1 (fr) * 2008-08-05 2010-02-11 日本曹達株式会社 Dérivé benzoylique substitué par sulfoxyimino et herbicide
CN101671286B (zh) * 2009-09-28 2011-02-23 北京颖泰嘉和分析技术有限公司 一种苯甲酰基-1,3-环己二酮类化合物的制备方法
WO2013124230A1 (fr) 2012-02-21 2013-08-29 Bayer Intellectual Property Gmbh Dérivés sulfinimidoyl- et sulfonimidoylbenzoyl à activité herbicide
WO2013124238A1 (fr) 2012-02-21 2013-08-29 Bayer Intellectual Property Gmbh Sulfinylaminobenzamides à action herbicide
CN104125949A (zh) * 2012-02-21 2014-10-29 拜耳知识产权有限责任公司 除草的3-(亚磺酰亚氨基/磺酰亚氨基)-苯甲酰胺

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998042678A1 (fr) * 1997-03-24 1998-10-01 Dow Agrosciences Llc Composes 1-alkyl-4-benzoyl-5-hydroxypyrazole et leur utilisation comme herbicides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998042678A1 (fr) * 1997-03-24 1998-10-01 Dow Agrosciences Llc Composes 1-alkyl-4-benzoyl-5-hydroxypyrazole et leur utilisation comme herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BOLM CARSTEN: "Catalytic coupling of aryl sulfonates with sp2-hybridized nitrogen nucleophiles", SYNTHESIS, no. 7, July 2000 (2000-07-01), pages 911 - 913, XP002978280 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2005291117B2 (en) * 2004-10-05 2011-06-09 Syngenta Limited Isoxazoline derivatives and their use as herbicides
US7465805B2 (en) 2004-10-05 2008-12-16 Syngenta Limited Isoxazoline derivatives and their use as herbicides
WO2006037945A1 (fr) * 2004-10-05 2006-04-13 Syngenta Limited Derives d’isoxazoline et leur utilisation comme herbicides
WO2008035737A1 (fr) * 2006-09-21 2008-03-27 Nippon Soda Co., Ltd. Dérivé de 4-nitrobenzoyle possédant un groupe sulfoxyimino et herbicide pour plante de riz
WO2009116290A1 (fr) * 2008-03-19 2009-09-24 日本曹達株式会社 Dérivés de 4-halogénobenzoyle ayant un groupe sulfoxyimino et herbicides
WO2010016230A1 (fr) * 2008-08-05 2010-02-11 日本曹達株式会社 Dérivé benzoylique substitué par sulfoxyimino et herbicide
CN101671286B (zh) * 2009-09-28 2011-02-23 北京颖泰嘉和分析技术有限公司 一种苯甲酰基-1,3-环己二酮类化合物的制备方法
WO2013124230A1 (fr) 2012-02-21 2013-08-29 Bayer Intellectual Property Gmbh Dérivés sulfinimidoyl- et sulfonimidoylbenzoyl à activité herbicide
WO2013124238A1 (fr) 2012-02-21 2013-08-29 Bayer Intellectual Property Gmbh Sulfinylaminobenzamides à action herbicide
CN104125949A (zh) * 2012-02-21 2014-10-29 拜耳知识产权有限责任公司 除草的3-(亚磺酰亚氨基/磺酰亚氨基)-苯甲酰胺
CN104136421A (zh) * 2012-02-21 2014-11-05 拜耳知识产权有限责任公司 具有除草活性的亚磺酰基氨基苯甲酰胺
JP2015508768A (ja) * 2012-02-21 2015-03-23 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 除草的に有効なスルフィニルアミノベンズアミド類
US9156784B2 (en) 2012-02-21 2015-10-13 Bayer Intellectual Property Gmbh Herbicidal sulfinimidoyl- and sulfonimidoyl benzoyl derivatives
US9198425B2 (en) 2012-02-21 2015-12-01 Bayer Intellectual Property Gmbh Herbicidally-effective sulfinyl aminobenzamides
EA026413B1 (ru) * 2012-02-21 2017-04-28 Байер Интеллектуэль Проперти Гмбх Гербицидно действующие сульфиниламинобензамиды

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