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WO2014119770A1 - Composé pyridazinone et herbicide comprenant celui-ci - Google Patents

Composé pyridazinone et herbicide comprenant celui-ci Download PDF

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WO2014119770A1
WO2014119770A1 PCT/JP2014/052366 JP2014052366W WO2014119770A1 WO 2014119770 A1 WO2014119770 A1 WO 2014119770A1 JP 2014052366 W JP2014052366 W JP 2014052366W WO 2014119770 A1 WO2014119770 A1 WO 2014119770A1
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group
alkyl
alkoxy
compound
atoms
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PCT/JP2014/052366
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Japanese (ja)
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荒木　知洋
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住友化学株式会社
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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
    • A01N43/48—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
    • A01N43/72—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
    • 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
    • C07D237/16—Two oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a pyridazinone compound and a herbicide containing the same.
  • An object of the present invention is to provide a compound having an excellent weed control effect.
  • the present inventors have found that a pyridazinone compound represented by the following formula (I) has an excellent weed control effect, and have reached the present invention. That is, the present invention is as follows.
  • R 2 is hydrogen, halogen, cyano group, nitro group, C 1-6 alkyl group, C 1-6 haloalkyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1-6 haloalkylthio group, C 1-6 haloalkylsulfinyl group, C 1-6 haloalkylsulfonyl group, C 3-8 cycloalkyl group, (C 3 -8 cycloalkyl) C 1-6 alkyl group, C 3-8 cycloalkoxy group, (C 3-8 cycloalkyl) C 1-6 alkoxy group, (C 1-6 alkylthio) C 1-6 alkoxy group, C 1-6 alkoxy) C 1-6 alkoxy group, C 3-6 alkenyloxy group, C 3-6 alkynyl
  • R 4 and R 5 may be the same or different and are hydrogen, halogen, C 1-3 alkyl group, C 1-3 haloalkyl group, C 2-4 alkenyl group, C 2-4 alkynyl group, C 1-3 Represents an alkoxy group, a C 1-3 haloalkoxy group or a C 3-8 cycloalkyl group,
  • A represents an aryl group of a monocyclic or bicyclic fused ring, or a monocyclic or bicyclic fused ring containing one or more atoms selected from the group consisting of nitrogen, oxygen and sulfur as a hetero atom.
  • C 6-10 aryl group (C 6-10 aryl optionally having one or more atoms or groups selected from group D) C 1-12 alkyl group, C 1-12 alkoxy group, C 3-8 A cycloalkoxy group, a C 3-12 alkenyloxy group, a C 3-12 alkynyloxy group, a C 6-10 aryloxy group optionally having one or more atoms or groups selected from the group D (from the group D C 6-10 aryl optionally having one or more atoms or groups selected) C 1-12 alkoxy group, (C 3-8 cycloalkyl) C 1-6 alkyl group, (C 1-6 alkoxy) C 1-6 An alkyl group, (C 3-8 cycloalkoxy) C 1-6 alkyl group, (C 1-6 alkylthio) C 1-6 alkyl group, (C 1-6 alkylsulfinyl) C 1-6 alkyl group, (C 1 -6 alkylsulfonyl) C 1-6
  • R 8 and R 9 may be the same or different and are a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 6-10 aryl group, a C 1-6 alkoxy group, a C 3-8 cycloalkoxy group.
  • R 10 represents hydrogen or a C 1-6 alkyl group
  • W is a phenyl group, a C 1-6 alkoxy group, a C 1-6 alkylthio group, a C 1-6 alkylsulfinyl group or a C 1-6 which may have one or more atoms or groups selected from the group D. Represents an alkylsulfonyl group.
  • R 6, R 7, R 8 , R 9 and W may be any of the groups represented by each of R 6, R 7, R 8 , R 9 and W have halogen, C 3-8 cycloalkyl group in R 6, R 6, R C 3-8 cycloalkoxy group in 8 and R 9, none of the heteroaryl group (C 1-6 alkyl) (C 6-10 aryl) aryl portion of the amino groups and 5-6 membered at R 8 and R 9 It may have a C 1-6 alkyl group.
  • ⁇ Represents any group represented by Group B: halogen, C 1-3 alkyl group, C 1-3 haloalkyl group, C 1-3 alkoxy group, C 1-3 haloalkoxy group, C 3-8 cycloalkyl group, C 2-4 alkenyl group, C 2-4 haloalkenyl, C 2-4 alkynyl group, C 1-3 alkylthio group, C 1-3 haloalkylthio group, C 1-3 alkylsulfinyl group, C 1-3 haloalkylsulfinyl group, C 1-3 alkyl Sulfonyl group, C 1-3 haloalkylsulfonyl group, nitro group, cyano group, (C 1-6 alkyl) carbonyl group, (C 1-6 alkoxy) carbonyl group, carbamoyl group, (C 1-3 alkyl) aminocarbonyl group , di (C 1-3 alkyl) aminocarbonyl group, (C
  • Group D Group consisting of halogen, C 1-6 alkyl group, C 1-3 haloalkyl group, C 1-3 alkoxy group, C 1-3 haloalkoxy group, C 1-3 alkylthio group, cyano group and nitro group.
  • the pyridazinone compound shown below (it is hereafter described as this invention compound).
  • A is a phenyl group, naphthyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, benzothiazolyl group, benzoxazolyl group, quinolinyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group or benzotriazinyl group
  • groups may have one or more atoms or groups selected from group B
  • G is hydrogen or the following formula [Wherein, R 6a may have one or more atoms or groups selected from a C 1-12 alkyl group, a C 1-12 haloalkyl group, a C 3-8 cycloalkyl group, and a group D 6.
  • R 2 is hydrogen, C 1-3 alkyl group, C 1-3 haloalkyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-8 cycloalkyl group, C 3-8
  • R 1 is a methyl group
  • R 2 is hydrogen, a methyl group or a methoxy group
  • R 3 is a methyl group, an ethyl group, a propyl group, a cyclopropyl group, a halogen or a halomethyl group
  • R 4 is hydrogen or a methyl group
  • A is a pyridyl group, a benzothiazolyl group, a benzoxazolyl group or a quinolinyl group, and these groups may have one or more atoms or groups selected from Group B, (Item 1) ) Pyridazinone compounds described.
  • R 3 is a methyl group, an ethyl group, a propyl group, or a cyclopropyl group
  • R 4 and R 5 are hydrogen
  • A is a pyridyl group, a benzothiazolyl group, a benzoxazolyl group, or a quinolinyl group, and these groups may have one or more atoms or groups selected from Group B. Compound.
  • (Item 9) A herbicide containing the pyridazinone compound according to any one of (Item 1) to (Item 8) as an active ingredient.
  • (Item 10) A method for controlling weeds, wherein an effective amount of the pyridazinone compound according to any one of items (Item 1) to (Item 8) is applied to weeds or soil where weeds grow.
  • the compound of the present invention has a weed control effect and is effective as an active ingredient of a herbicide.
  • the substituent in the present invention will be described.
  • the halogen include fluorine, chlorine, bromine and iodine.
  • the C 1-3 alkyl group means an alkyl group having 1 to 3 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
  • the C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, 2,2-dimethylpropyl group, butyl group, isobutyl group, sec -Butyl group, tert-butyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, pentyl group, hexyl group and isohexyl group can be mentioned.
  • C 1-12 alkyl group means an alkyl group having 1 to 12 carbon atoms, for example, methyl group, ethyl group, propyl group, isopropyl group, 1-methylpropyl group, 2-methylpropyl group, 1-ethyl group.
  • the halomethyl group means a methyl group having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethyl group, a difluoromethyl group, a bromomethyl group and a chloromethyl group.
  • the C 1-3 haloalkyl group means an alkyl group having 1 to 3 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethyl group, a chloromethyl group, and 2,2-difluoroethyl.
  • the C 1-6 haloalkyl group means an alkyl group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethyl group, a chloromethyl group, and 2,2-difluoroethyl.
  • the C 1-12 haloalkyl group means an alkyl group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethyl group, a chloromethyl group, and 2,2-difluoroethyl.
  • 2,2,2-trichloroethyl group 2,2,2-trifluoroethyl group, 2,2,2-trifluoro-1,1-dichloroethyl group, 2,2-difluorohexyl group, 1, A 1-difluorododecyl group may be mentioned.
  • the C 3-8 cycloalkyl group means a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
  • (C 3-8 cycloalkyl) C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms having a cycloalkyl group having 3 to 8 carbon atoms, such as a cyclopropylmethyl group and a cyclopentylmethyl group. Is mentioned.
  • the C 2-4 alkenyl group means an alkenyl group having 2 to 4 carbon atoms, and examples thereof include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
  • the C 3-4 alkenyl group means an alkenyl group having 3 to 4 carbon atoms, and examples thereof include an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
  • the C 2-12 alkenyl group means an alkenyl group having 2 to 12 carbon atoms, for example, vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 5-hexenyl group and 11 -A dodecenyl group is mentioned.
  • the C 2-4 alkynyl group means an alkynyl group having 2 to 4 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, and a 2-butynyl group.
  • the C 3-4 alkynyl group means an alkynyl group having 3 to 4 carbon atoms, and examples thereof include a propargyl group and a 2-butynyl group.
  • the C 2-12 alkynyl group means an alkynyl group having 2 to 12 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, a 2-butynyl group, a 5-hexynyl group, and an 11-dodecynyl group.
  • the C 1-3 alkoxy group means an alkoxy group having 1 to 3 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a normal propyloxy group, and an isopropyloxy group.
  • the C 1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, 2-methylpropoxy group, 3-methylpropoxy group.
  • the C 1-12 alkoxy group means an alkoxy group having 1 to 12 carbon atoms, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group, 2-methylpropoxy group, 3-methylpropoxy group.
  • the C 1-3 haloalkoxy group means an alkoxy group having 1 to 3 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethoxy group, 2,2-difluoroethoxy group, 2 2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, and 3,3-difluoropropyloxy group.
  • the C 1-6 haloalkoxy group means an alkoxy group having 1 to 3 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2 2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group and 6-fluorohexyloxy group.
  • a halogen such as fluorine, chlorine, bromine or iodine
  • the C 1-6 alkylthio group means an alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, and an isopropylthio group.
  • the C 1-6 alkylsulfinyl group means an alkylsulfinyl group having 1 to 6 carbon atoms, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, and an isopropylsulfinyl group.
  • the C 1-6 alkylsulfonyl group means an alkylsulfonyl group having 1 to 6 carbon atoms, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, and an isopropylsulfonyl group.
  • the C 1-6 haloalkylthio group means an alkylthio group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trichloromethylthio group, a trifluoromethylthio group, and 2,2-difluoro. Examples thereof include an ethylthio group, a 2,2,2-trifluoroethylthio group, a 2,2,2-trichloroethylthio group, and a 3-chloropropylthio group.
  • the C 1-6 haloalkylsulfinyl group means an alkylsulfinyl group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trichloromethylsulfinyl group, a trifluoromethylsulfinyl group, 2, Examples include 2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2,2,2-trichloroethylsulfinyl group and 3-chloropropylsulfinyl group.
  • the C 1-6 haloalkylsulfonyl group means a C 1-6 alkylsulfonyl group having a halogen such as fluorine, chlorine, bromine, iodine, etc., and examples thereof include a trichloromethylsulfonyl group, a trifluoromethylsulfonyl group, 2, Examples include 2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group and 3-chloropropylsulfonyl group.
  • the C 3-8 cycloalkoxy group means a cycloalkoxy group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyloxy group, a cyclopentyloxy group, and cyclohexyloxy.
  • (C 3-8 cycloalkyl) C 1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms having a cycloalkyl group having 3 to 8 carbon atoms, such as a cyclopropylmethoxy group, 1-cyclo Examples thereof include a propylethoxy group and a cyclopentylmethoxy group.
  • C 1-6 alkylthio C 1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms bonded to an alkylthio group having 1 to 6 carbon atoms.
  • a methylthiomethoxy group, a methylthioethoxy group, a methylthio Examples include a propoxy group, an ethylthiomethoxy group, and an ethylthioethoxy group.
  • the C 1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms bonded to an alkoxy group having 1 to 6 carbon atoms.
  • methoxymethoxy group ethoxymethoxy group
  • methoxymethoxy group normal examples thereof include a propyloxymethoxy group, an isopropyloxymethoxy group, a 2-methoxyethoxy group, a 2-ethoxyethoxy group, and a 3-methoxypropyloxy group.
  • the C 3-6 alkenyloxy group means an alkenyloxy group having 3 to 6 carbon atoms, and examples thereof include an allyloxy group and a 2-butenyloxy group.
  • the C 3-12 alkenyloxy group means an alkenyloxy group having 3 to 12 carbon atoms, and examples thereof include an allyloxy group, a 2-butenyloxy group, a 5-hexenyloxy group, and an 11-dodecenyloxy group.
  • the C 3-6 alkynyloxy group means an alkynyloxy group having 3 to 6 carbon atoms, and examples thereof include a propargyloxy group and a 2-butynyloxy group.
  • the C 3-12 alkynyloxy group means an alkynyloxy group having 3 to 12 carbon atoms, and examples thereof include a propargyloxy group, a 2-butynyloxy group, a 5-hexynyloxy group, and an 11-dodecynyloxy group.
  • the cyano C 1-6 alkoxy group means a C 1-6 alkoxy group having a cyano group, such as a cyanomethoxy group, a 1-cyanomethoxy group, a 2-cyanoethoxy group, and a 3-cyanopropyloxy group.
  • (C 1-6 alkoxy) carbonyl C 1-6 alkoxy group means a C 1-6 alkoxy group bonded to a carbonyl group having (C 1-6 alkoxy group), for example, methoxy Examples thereof include a carbonylmethoxy group and an ethoxycarbonylmethoxy group.
  • the carbamoyl C 1-6 alkoxy group means a C 1-6 alkoxy group having a carbamoyl group, and examples thereof include a carbamoylmethoxy group.
  • ⁇ (C 1-6 alkyl) aminocarbonyl ⁇ C 1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms bonded to (an aminocarbonyl group having an alkyl group having 1 to 6 carbon atoms);
  • An example is a methylaminocarbonylmethoxy group.
  • ⁇ Di (C 1-6 alkyl) aminocarbonyl ⁇ C 1-6 alkoxy group is bonded to ⁇ (carbonyl group bonded to two identical or different amino groups having 1 to 6 carbon atoms) ⁇ Means an alkoxy group having 1 to 6 carbon atoms, and examples thereof include a dimethylaminocarbonylmethoxy group.
  • the C 1-6 alkylamino group means an alkylamino group having 1 to 6 carbon atoms, and examples thereof include a methylamino group, an ethylamino group, and an isopropylamino group.
  • the di (C 1-6 alkyl) amino group means an amino group having two identical or different alkyl groups having 1 to 6 carbon atoms, and examples thereof include a dimethylamino group, a diethylamino group, and an ethylmethylamino group. It is done.
  • the (C 1-6 alkyl) carbonylamino group means an amino group bonded to a carbonyl group having an alkyl group having 1 to 6 carbon atoms, and examples thereof include an acetamido group and a propionylamino group.
  • the hydroxy C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms having a hydroxyl group, and examples thereof include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group. Can be mentioned.
  • (C 1-6 alkoxy) C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an alkoxy group having 1 to 6 carbon atoms, such as a methoxymethyl group or 1-methoxyethyl group. Group, ethoxymethyl group, propoxymethyl group, butoxymethyl group, 1-methyl 2-methoxyethyl group and 2-ethoxyethyl group.
  • (C 1-6 haloalkoxy) C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms which is bonded to (an alkoxy group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine).
  • C 3-8 cycloalkoxy means an alkyl group having 1 to 6 carbon atoms bonded to a cycloalkoxy group having 3 to 8 carbon atoms, such as a cyclopropyloxymethyl group and cyclopentyl.
  • An oxymethyl group is mentioned.
  • ⁇ (C 3-8 cycloalkyl) C 1-6 alkoxy ⁇ C 1-6 alkyl group is bonded to ⁇ (C 1-6 alkoxy group bonded to C 3-8 cycloalkyl group) ⁇ .
  • C 1-6 alkylthio C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthiomethyl group and 1- (methylthio) group. Examples include an ethyl group, an ethylthiomethyl group, a propylthiomethyl group, a butylthiomethyl group, a 1-methyl-2- (methylthio) ethyl group, and a 2- (ethylthio) ethyl group.
  • the C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an alkylsulfinyl group having 1 to 6 carbon atoms, such as a methylsulfinylmethyl group and ethylsulfinyl group. A methyl group is mentioned.
  • (C 1-6 alkylsulfonyl) C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an alkylsulfonyl group having 1 to 6 carbon atoms, such as a methylsulfonylmethyl group, ethylsulfonyl A methyl group and 2- (methylsulfonyl) ethyl group are mentioned.
  • (C 1-6 haloalkylthio) C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms which is bonded to (an alkylthio group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine). And examples thereof include a trifluoromethylthiomethyl group, a 2,2-difluoroethylthiomethyl group, and a 2,2,2-trifluoroethylthiomethyl group.
  • the cyano C 1-6 alkyl group means a C 1-6 alkyl group having a cyano group, and examples thereof include a cyanomethyl group, a 1-cyanoethyl group, a 2-cyanoethyl group, and a 3-cyanoethyl group.
  • the hydroxyimino C 1-6 alkyl group means a C 1-6 alkyl group having a hydroxyimino group, and examples thereof include a hydroxyiminomethyl group.
  • the (C 1-6 alkoxy) imino C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an imino group bonded to (an alkoxy group having 1 to 6 carbon atoms), for example, methoxy Examples include iminomethyl group and ethoxyiminomethyl group.
  • the (C 1-6 alkyl) carbonyl group means a carbonyl group bonded to an alkyl group having 1 to 6 carbon atoms, and examples thereof include an acetyl group, a propionyl group, and a butyryl group.
  • Examples of the monocyclic or bicyclic condensed ring aryl group include a 5- or 6-membered monocyclic aryl group, or a 6-6-membered or 6-5-membered bicyclic fused ring aryl group, Examples thereof include a phenyl group, a naphthyl group, an indanyl group, and a 1,2,3,4-tetrahydronaphthyl group.
  • a heteroaryl group of a monocyclic or bicyclic fused ring containing one or more atoms selected from the group consisting of nitrogen, oxygen and sulfur as a heteroatom is a heteroatom selected from the group consisting of nitrogen, oxygen and sulfur.
  • a heteroaryl group of a membered bicyclic fused ring such as a furyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, Oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, 1,2,4-oxadiazolyl group, 1,3,4-oxadiazolyl group, 1,2,5-oxadiazolyl group, 1,2 3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,3,4-thiadiazolyl group, 1,2,5-thiadiazolyl group, pyridyl group, pyridyl group
  • the C 2-6 alkenyl group means an alkenyl group having 2 to 6 carbon atoms, and examples thereof include a vinyl group, an allyl group, a 1-buten-3-yl group, and a 3-buten-1-yl group.
  • the C 2-6 alkynyl group means an alkynyl group having 2 to 6 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, and a 2-butynyl group.
  • the C 6-10 aryl group means an aryl group having 6 to 10 carbon atoms, and examples thereof include a phenyl group and a naphthyl group.
  • (C 6-10 aryl) C 1-6 alkyl group means an alkyl group having 1 to 6 carbon atoms bonded to an aryl group having 6 to 10 carbon atoms, and examples thereof include a benzyl group and a phenethyl group.
  • the (C 6-10 aryl) C 1-12 alkyl group means an alkyl group having 1 to 12 carbon atoms bonded to an aryl group having 6 to 10 carbon atoms, and examples thereof include a benzyl group and a 1-phenylethyl group.
  • the C 6-10 aryloxy group means an aryloxy group having 6 to 10 carbon atoms, and examples thereof include a phenoxy group and a naphthyloxy group.
  • the (C 6-10 aryl) C 1-6 alkoxy group means an alkoxy group having 1 to 6 carbon atoms bonded to an aryl group having 6 to 10 carbon atoms.
  • a benzyloxy group and a phenethyloxy group are Can be mentioned.
  • the (C 6-10 aryloxy) C 1-12 alkyl group means an alkyl group having 1 to 12 carbon atoms bonded to an aryloxy group having 6 to 10 carbon atoms, such as a phenoxymethyl group, 2- Examples include phenoxyethyl group, 1-methyl-2-phenoxyethyl group, and 3-phenoxypropyl group.
  • the (C 6-10 arylthio) C 1-12 alkyl group means an alkyl group having 1 to 12 carbon atoms bonded to an arylthio group having 6 to 10 carbon atoms, such as a phenylthiomethyl group, 2-phenyl A thioethyl group, a 1-methyl-2-phenylthioethyl group and a 3-phenylthiopropyl group can be mentioned.
  • (C 6-10 aryl) C 1-12 alkoxy group means an alkoxy group having 1 to 12 carbon atoms bonded to an aryl group having 6 to 10 carbon atoms, and examples thereof include a benzyloxy group, a phenethyloxy group, A 3-phenylpropyloxy group, a 6-phenylhexyloxy group, and a 12-phenyldodecyloxy group may be mentioned.
  • ⁇ (C 6-10 aryl) C 1-6 alkoxy ⁇ C 1-6 alkyl group is bonded to ⁇ (C 1-12 alkoxy group bonded to C 6-10 aryl group) ⁇ .
  • the di (C 3-6 alkenyl) amino group means an amino group having two identical or different alkenyl groups having 3 to 6 carbon atoms, for example, a diallylamino group and a di (3-butenyl) amino group.
  • (C 1-6 alkyl) (C 6-10 aryl) amino group means an amino group having an alkyl group having 1 to 6 carbon atoms and a C 6-10 aryl group, for example, methylphenylamino group and ethyl group A phenylamino group is mentioned.
  • the 5- to 6-membered heteroaryl group means an aromatic 5- or 6-membered heterocyclic group containing 1 to 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur. Examples include a pyridyl group, a 3-thienyl group, and a 1-pyrazolyl group.
  • the C 2-4 haloalkenyl group means an alkenyl group having 2 to 4 carbon atoms having halogen such as fluorine, chlorine, bromine, iodine, etc., for example, 2,2-difluorovinyl group and 2,2 -A dichlorovinyl group is mentioned.
  • the C 1-3 alkylthio group means an alkylthio group having 1 to 3 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, and a propylthio group.
  • the C 1-3 haloalkylthio group means an alkylthio group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trichloromethylthio group, a trifluoromethylthio group and 2,2-difluoro Examples thereof include an ethylthio group, a 2,2,2-trifluoroethylthio group, a 2,2,2-trichloroethylthio group and a 3-chloropropylthio group.
  • the C 1-3 alkylsulfinyl group means an alkylsulfinyl group having 1 to 3 carbon atoms, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, and a propylsulfinyl group.
  • the C 1-3 haloalkylsulfinyl group means an alkylsulfinyl group having 1 to 3 carbon atoms having halogen such as fluorine, chlorine, bromine and iodine, and examples thereof include a trifluoromethylsulfinyl group.
  • the C 1-3 alkylsulfonyl group means an alkylsulfonyl group having 1 to 3 carbon atoms, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, and an isopropylsulfonyl group.
  • the C 1-3 haloalkylsulfonyl group means an alkylsulfonyl group having 1 to 6 carbon atoms having a halogen such as fluorine, chlorine, bromine or iodine, and examples thereof include a trichloromethylsulfonyl group, a trifluoromethylsulfonyl group, 2, Examples include 2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group and 3-chloropropylsulfonyl group.
  • the (C 1-6 alkoxy) carbonyl group means a carbonyl group bonded to (an alkoxy group having 1 to 6 carbon atoms), and examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, and a normal hexyloxycarbonyl group.
  • the (C 1-3 alkyl) aminocarbonyl group means a carbonyl group bonded to an amino group having (alkyl group having 1 to 3 carbon atoms), and examples thereof include a methylaminocarbonyl group.
  • the di (C 1-3 alkyl) aminocarbonyl group means a carbonyl group bonded to an amino group having two identical or different alkyl groups having 1 to 3 carbon atoms, and examples thereof include a dimethylaminocarbonyl group. .
  • the (C 3-8 cycloalkyl) carbonylamino group means a carbonylamino group bonded to (a cycloalkyl group having 3 to 8 carbon atoms), and examples thereof include a cyclopropylcarbonylamino group and a cyclohexylcarbonylamino group.
  • the (C 1-6 alkoxy) carbonylamino group means a carbonylamino group bonded to (an alkoxy group having 1 to 6 carbon atoms), and examples thereof include a methoxycarbonylamino group.
  • (C 1-3 alkoxy) C 1-3 alkyl group means an alkyl group having 1 to 3 carbon atoms which is bonded to (an alkoxy group having 1 to 3 carbon atoms), and examples thereof include a methoxymethyl group and 1-methoxy group. Examples include an ethyl group, an ethoxymethyl group, and a 2-ethoxyethyl group.
  • the pyridazinone compound represented by the formula (I) may take the form of an agriculturally acceptable salt with an inorganic base or an organic base.
  • salts include inorganic bases (eg, alkali metal (lithium, sodium, potassium, etc.) hydroxides, carbonates, hydrogen carbonates, acetates, hydrides, alkaline earth metals (magnesium, calcium, Hydroxide), hydride, etc., ammonia), organic bases (eg, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylamine, benzylamine, ethanolamine, diethanolamine, pyridine, collidine, etc.), Examples thereof include salts formed by mixing with metal alkoxides (for example, sodium methoxide, potassium tert-butoxide, magnesium methoxide and the like).
  • the compound of the present invention When the compound of the present invention has one or more asymmetric centers, the compound has two or more stereoisomers (for example, enantiomers, diastereomers, etc.). The compound of the present invention includes all of these stereoisomers and a mixture of any two or more thereof.
  • the compound of the present invention has geometric isomerism based on a double bond or the like, the compound contains two or more geometric isomers (for example, E / Z or trans / cis isomers, S-trans / S-cis). Each isomer) and the like.
  • the compounds of the present invention include all of these geometric isomers and mixtures of any two or more thereof.
  • G 21 is hydrogen or the following formula ⁇ Wherein L represents oxygen or sulfur, R 61 is a C 1-6 alkyl group, a C 1-3 haloalkyl group, a C 3-6 cycloalkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, or one or more atoms or groups selected from the group C good C 6-10 aryl group optionally having, (1 or more atoms or optionally C 6-10 aryl optionally having a group selected from group C) C 1-6 alkyl, C 1-6 An alkoxy group, a C 3-8 cycloalkoxy group, a C 3-6 alkenyloxy group, a C 3-6 alkynyloxy group, a C 6-10 aryl optionally having one or more atoms or groups selected from the group C An oxy group, (C 6-10 aryl optionally having one or more atoms or groups selected from group C) C
  • R 81 and R 91 may be the same or different and are a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 6-10 aryl group, a C 1-6 alkoxy group, a C 3-8 cycloalkoxy group.
  • R 101 represents hydrogen or a C 1-6 alkyl group
  • W 21 is a phenyl group optionally having one or more atoms or groups selected from group C;
  • Any one of the groups represented by Group C represents a halogen, a C 1-3 alkyl group, a C 1-3 haloalkyl group, a C 1-3 alkoxy group or a nitro group.
  • R 21 is hydrogen, a C 1-3 alkyl group, a C 1-3 haloalkyl group, a C 1-6 alkoxy group, or a C 1-6 haloalkoxy.
  • a compound which is a group, a C 3-8 cycloalkyl group, a C 3-8 cycloalkoxy group or a (C 3-8 cycloalkyl) C 1-6 alkoxy group [Aspect 5] In [Aspect 4], R 21 is a C 1-3 alkyl group, [Aspect 6] In [Aspect 5], R 21 is a methyl group, [Aspect 7] In [Aspect 6], R 21 is a C 1-6 alkoxy group, [Aspect 8] In [Aspect 7], R 21 is a methoxy group,
  • A represents an aryl group of a monocyclic or bicyclic fused ring, or a group consisting of nitrogen, oxygen and sulfur as a hetero atom.
  • G 21 is hydrogen or the following formula:
  • R 61a is selected from a C 1-6 alkyl group, a C 3-6 cycloalkyl group, a C 1-6 alkoxy group, a C 3-6 alkenyloxy group, a C 3-6 alkynyloxy group, and a C group.
  • W 21a is A compound which is a phenyl group optionally having one or more atoms or groups selected from a C 1-3 alkoxy group or a group C; [Aspect 34] In [Aspect 33], a compound wherein G 21 is hydrogen, [Aspect 35] In [Aspect 33], a compound wherein G 21 is a (C 1-6 alkyl) carbonyl group, [Aspect 36] In [Aspect 33], a compound wherein G 21 is an acetyl group, [Aspect 37] In [Aspect 33], a compound wherein G 21 is a propionyl group, [Aspect 38] In [Aspect 33], a compound wherein G 21 is an isobutyryl group, [Aspect 39] In [Aspect 33], a compound wherein G 21 is a pivaloyl group
  • W 21b represents a phenyl group which may have a C 1-6 alkoxy group or a nitro group.
  • ⁇ Represents any group represented by: ]
  • R 2 is hydrogen, a C 1-3 alkyl group, a C 1-3 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, C A compound which is a 3-8 cycloalkyl group, a C 3-8 cycloalkoxy group or a (C 3-8 cycloalkyl) C 1-6 alkoxy group, [Aspect 60] In [Aspect 59], a compound wherein R 2 is a C 1-3 alkyl group, [Aspect 61] In [Aspect 60], a compound wherein R 2 is a methyl group, [Aspect 62] In [Aspect 59], a compound wherein R 2 is a C 1-6 alkoxy group, [Aspect 63] In [Aspect 62], a compound wherein R 2 is a methoxy group,
  • A is a phenyl group, naphthyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, benzothiazolyl group, benzoxazolyl group, quinolinyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group Or a benzotriazinyl group, and these groups may have one or more atoms or groups selected from group B, [Aspect 73] In any one of [Aspect 57] to [Aspect 71], A is a phenyl group, naphthyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, benzothiazolyl group, benzoxazolyl group, quinolinyl group, A cinnolinyl group, a quinazoliny
  • G is hydrogen or the following formula (In the formula, R 6a , R 7a and W a represent the same meaning as described above.)
  • R 1 represents a methyl group
  • R 2 represents hydrogen, a methyl group or a methoxy group
  • A represents a pyridyl group, a benzothiazolyl group, a benzoxazolyl group or a quinolinyl group.
  • the herbicide of the present invention contains the compound of the present invention and an inert carrier.
  • the inert carrier include a solid carrier, a liquid carrier, and a gas carrier.
  • the herbicide of the present invention is usually further added with formulation adjuvants such as surfactants, sticking agents, dispersants, stabilizers, etc., wettable powder, wettable powder, flowable powder, granules, dry flowable powder, It is formulated into emulsions, aqueous liquids, oils, smokes, aerosols, microcapsules and the like.
  • the herbicide of the present invention usually contains the compound of the present invention in a weight ratio of 0.1 to 80%.
  • the inert carrier examples include a solid carrier, a liquid carrier, and a gas carrier.
  • the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon,
  • the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like.
  • Hydrogens eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene
  • aliphatic hydrocarbons eg, n-hexane, cyclohexane, kerosene
  • esters eg, ethyl acetate, butyl acetate
  • nitriles eg, , Acetonitrile, isobutylnitrile
  • ethers eg Dioxane, diisopropyl ether
  • acid amides for example, N, N-dimethylformamide (hereinafter referred to as DMF), dimethylacetamide
  • halogenated hydrocarbons for example, dichloroethane, trichloroethylene, carbon tetrachloride
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.
  • formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.
  • fixing agents and dispersants specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for
  • the method for controlling weeds of the present invention includes a step of applying an effective amount of the compound of the present invention to a place where weeds or weeds will or will grow.
  • the herbicide of the present invention is usually used.
  • Examples of the method of applying the herbicide of the present invention include a method of treating the herbicide of the present invention with foliage on weeds, a method of treating the herbicide of the present invention on the soil surface on which weeds will grow or will grow, and the present invention. And a method of treating the herbicide of the present invention with the surface water of a paddy field flooded in a place where the weeds will grow or will grow.
  • the compound of the present invention is usually used in an amount of 1 to 5000 g, preferably 10 to 1000 g, per 10,000 m 2 of area for controlling weeds.
  • the compound of the present invention can be used in farmland or the like where the “plants” listed below are cultivated.
  • Plant crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, hop, etc.
  • Vegetables Eggplant vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), cucurbits vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, cucumbers, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (eg, leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American Bow Fu etc.), Rubiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (silla, mint, basil etc.), legumes (peas, kidney beans, azuki bean, broad beans, chickpea etc.), strawberries, sweet potatoes, yam, taro , Konjac, Ginger, Oh La or the like.
  • Fruit trees fruits (apples, pears, pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prunes, etc.), citrus (citrus oranges, oranges, lemons, limes, grapefruits) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
  • Trees other than fruit trees tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, eustoma, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, black beetle, Japanese amberjack, eel, pine, pine, spruce, yew, elm, redwood, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi.
  • plants include genetically modified plants.
  • the compound of the present invention can be mixed or used in combination with other herbicides, safeners, plant growth regulators, insecticides, acaricides, nematicides, fungicides and / or synergists.
  • Triazine-based herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simethrin, dimethmethrin (methymethrin) metribuzin), triaziflam, indaziflam and the like;
  • Dinitroaniline herbicidal compound pendimethalin, prodiamine, trifluralin, etc .;
  • Organophosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate -P (glufosinate-P), bialaphos, etc .;
  • Acid amide-based herbicidal compound propanil, propyzamide, bromobutide, etobenzanide and the like;
  • Cyclic imide-based herbicidal compounds oxadiazon, cinidone-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, Flumioxazin, pyraflufen-ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenzene bencar azone), saflufenacil (saflufenacil) and the like;
  • Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, tefriltrione, tefuryltrione )etc;
  • Trionoxime herbicidal compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloproxidim, cyclohexyloxydim Tralcoxydim, profoxydim, etc .;
  • sulfonylurea herbicidal compounds chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron methyl (Tribenuron-methyl), triasulfuron (triasulfuron), bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-thylfuryl-urmethyl-uryl Nicosulfuron (nic sulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron-thursulfuron (thulsulfuron), prosulfuron , Triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupylsulfuron, sulfosulfuron, azulfurium Ruflon, ethoxysulfuron, oxasulfuron,
  • Sulfonamide-based herbicidal compounds flumesulam, metosulam, dicloslam, floraslam, chloransrammethyl, penoxsulx, penoxsulx, penoxsulx
  • Examples of the active ingredient of such a drug reducing agent include the following. Benoxacol, cloquintocet-mexyl, ciomethrinil, dichlormid, fenchlorazole (fluzolazole), fenchlorimole (fluchlorzole) Mefenpyr-diethyl, MG191, oxabetrinil, alidochlor, isoxadifen-ethyl, cyprosulfamide, fluoxphenim ), 1,8-naphthalic anhydride (1,8-naphthalic anhydride), AD-67.
  • Examples of the active ingredient of such a plant growth regulator include the following. Hymexazole, paclobutrazol, uniconazole-P, inabenfide, prohexadione-calcium, abiglycinyl aviglycine , Abscisic acid, indolebutyric acid, ethiclozate, etephon, cloxyfonac, chlormequat, dichlorprop di, dichlorprop di (Gibberellins), prohydrojasmon, benzylaminopurine, forchlorfenuron, maleic hydrazide, maleic hydride, calcium peroxide chloride), 4-CPA (4-chlorophenoacetic acid).
  • Examples of the active ingredient of such an insecticide include the following. (1) Organophosphorus compound Acephate, Butathiofos, Chlorethoxyphos, Chlorfenvinfos, Chlorpyrifos, Chlorpyrifos-Methyl (Chlorpyrifos) , Diazinon, diclofenthion (ECP), dichlorvos (DDVP), dimethoate, dimethylvinphos, disulfoton, EPth, ethione Lofos, etrimfos, fenthion (MPP), phennitrothion (MEP), fothiazate, formothion, thoxathion, isoxathion, isoxathion, isoxathion (Mesulfofos), methidathion (DMTP), monocrotophos, monored (BRP), oxydeprofos (ESP), parathion, phosalone, phosmetone hosmet: PMP,
  • Nereistoxin compound Cartap bensultap, thiocyclam, monosultap, bisultap.
  • Neonicotinoid compounds Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran (dinoteurin)
  • Benzoylurea compounds Chlorfluazuron, bistrifluron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron (flufluxuron) hexafluuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
  • Phenylpyrazole compound Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole.
  • insecticidal active ingredients machine oil, nicotine sulfate (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorfenacyl (chlorophylline) ), DCIP (dichloropropionic ether), DD (1,3-Dichloropropene), emamectin benzoate, phenazaquin, flupyrazophos, tropurene, hydropyrene , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosulfur, inspiramide, spinomidol tolfenpyrad, triazamate, fulbenamide, flumectin, lepimectin, aluminum phosphide, arsenous oxide, benclothiaz (benclothiaz) ium cyanamide, calcium polysulful
  • X a1 represents a methyl group, chlorine, bromine or fluorine
  • X a2 represents fluorine, chlorine, bromine, a C 1 -C 4 haloalkyl group or a C 1 -C 4 haloalkoxy group
  • X a3 represents fluorine
  • X a4 is optionally substituted C 1 -C 4 alkyl, optionally substituted C 3 -C 4 alkenyl, optionally substituted C 3 -C 4 alkynyl, substituted is represents an C 3 -C 5 cycloalkylalkyl or hydrogen even if, X a5 represents hydrogen or methyl, X a6 represents hydrogen, fluorine or chlorine, X a7 represents hydrogen, fluorine or chlorine. )
  • X b2 represents an optionally substituted C 1 -C 4 haloalkyl group such as a 2,2,2-trifluoroethyl group or an optionally substituted C 3 -C 6 cycloalkyl such as a cyclopropyl group.
  • X b3 represents an optionally substituted C 1 -C 4 alkyl group such as methyl
  • X b4 represents hydrogen, chlorine, a cyano group, or a methyl group.
  • X c1 is 3,3,3-trifluoropropyl optionally substituted C 1 -C 4 alkyl group such as a group, it may be substituted, such as 2,2,2-trichloro ethoxy C 1 -C 4 alkoxy group, 4-cyano represents optionally substituted phenyl or 2-chloro-3-optionally substituted pyridyl group such as a phenyl group, X c2 represents a methyl group Alternatively, it represents a trifluoromethylthio group, and X c3 represents a methyl group or a halogen.)
  • Examples of the active ingredient of such an acaricide include the following. Acequinocyl, amitraz, benzoximate, bifenazate, bromopropyrate, chinomethionate, BS chlorbenzylate clofenetine, cyflumethofen, kelsen (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate , Fluacrylpyrim, halfenprox, hexythiazodi, propargite tetrapene, fendipenti, pyridene, pyridene ), Spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cienopyrafen.
  • Examples of the active ingredient of such a nematicide include the following. DCIP, fothiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imicyafos.
  • Examples of the active ingredient of such a bactericide include the following. (1) Polyhaloalkylthio compound Captan, folpet, etc.
  • Carboxamide compounds Carboxin, mepronil, flutolanil, thifluzamide, furametopyr, boscalid, pentiopyrad, etc.
  • Azole compounds Triadimefon, triadimenol, propiconazole, tebuconazole, cyproconazole, epoxiconol, and epoxiconazole ), Ipconazole, triflumizole, prochloraz, penconazole, flusilazole, dinicoazole, bromconazole, bromconazole, bromconazole, bromconazole Difenoconazole, metconazole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluconazole, fluconazole, fluconazole, fluconazole. tritonicazole, bittertanol, imazalil, flutriafol, etc.
  • Morpholine compound Dodemorph, tridemorph, fenpropimorph, and the like.
  • Strobilurin compounds azoxystrobin, cresoxime-methyl, methminostrobin, trifloxystrobin, picoxystrobin (picoxystrobin), cross Fluoxastrobin, dimoxystrobin, etc.
  • Examples of the active ingredient of such a synergist include the following. Piperonyl butoxide, sesamex, sulfoxide, N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide (MGK 264), N - decremental imidazole (N-declyimidazole), WARF- anti resistant (WARF-antiresistant), TBPT, TPP, IBP, PSCP, methyl iodide (CH 3 I), t- phenyl Bed tenon (t-phenylbutenone), diethyl Maleate maleate, DMC, FDMC, ETP, and ETN.
  • Examples of the control target of the herbicide of the present invention include the following. Crabgrass (Digitaria ciliaris), goosegrass (Eleusine indica), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), Kin green foxtail (Setariaglauca), barnyardgrass (Echinochloa crus-galli), fall panicum (Panicum dichotomiflorum), Texas Pani cam (Panicum texanum ), Mushroom millet (Brachiaria platyphylla), Alexander glass (Brachiaria plantagenea), Suriname glass (Brachiaria decumbens), Sebum sorghum (Sorghum halepense), Shutokeke Emissions (Andropogon sorghum), bermudagrass (Cynodon dactylon), oats (Avena fatua), darnel (Lolium multiflorum), black grass (Alopecurus myosuroides), downy brome (Bro
  • Potamogeton Pectinatus Water meal (Wolffia genus), water mills foil such (Myriophyllum spicatum, Myriophyllum heterophyllum etc.), water hyacinth (Eichhornia crassipes) or the like aquatic plants.
  • the compound of the present invention can be produced, for example, by the following production method.
  • Manufacturing method 1 Among the compounds of the present invention, a compound represented by formula (Ia) in which G is hydrogen can be produced by reacting a compound represented by formula (II), a compound represented by formula (III) and a base. it can.
  • X 1 represents fluorine or chlorine
  • R 1 , R 2 , R 3 , R 4 , R 5 and A represent the same meaning as described above.
  • This reaction is usually performed in a solvent.
  • Examples of the solvent that can be used include aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, dioxane, tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane; dimethylformamide (hereinafter referred to as DMF). ) Such as dimethyl sulfoxide (hereinafter referred to as DMSO); nitriles such as acetonitrile; ketones such as acetone or a mixed solvent thereof.
  • Examples of the base used in this reaction include metal alkoxides such as potassium tert-butoxide, and inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride.
  • the amount of the compound represented by formula (III) used in this reaction is usually 0.5 to 3 molar equivalents, preferably 1 to 2 molar equivalents, relative to the compound represented by formula (II).
  • the amount of the base used in this reaction is usually 1 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound represented by the formula (II).
  • the reaction temperature of this reaction is usually 0 to 200 ° C., preferably 20 to 100 ° C.
  • the reaction time for this reaction is usually 10 minutes to 30 hours. After completion of this reaction, for example, the reaction mixture is neutralized by adding an acid, mixed with water, extracted with an organic solvent, the obtained organic layer is dried, concentrated, purified by silica gel column chromatography, etc. By performing the operation, the compound represented by the formula (Ia) can be isolated.
  • the compound represented by the formula (III) is a known compound or can be produced from a known compound.
  • the compound represented by the formula (Ib) in which G is a group other than hydrogen is reacted with a compound represented by the formula (Ia), a compound represented by the formula (IV), and a base.
  • G 1 represents other than hydrogen in the definition of G
  • X 2 represents chlorine, bromine, or iodine
  • R 1 , R 2 , R 3 , R 4 , R 5 and A have the same meaning as described above. Represents.
  • This reaction is usually performed in a solvent.
  • Examples of the solvent that can be used include aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, dioxane, THF, and dimethoxyethane; amides such as DMF; sulfoxides such as DMSO; Nitriles; ketones such as acetone or a mixed solvent thereof.
  • Examples of the base used in this reaction include inorganic bases such as potassium carbonate, cesium carbonate, and sodium hydride; organic bases such as triethylamine, pyridine, and 1,8-diazabicyclo [5.4.0] -7-undecene. Can be mentioned.
  • the amount of the compound represented by formula (IV) used in this reaction is usually 0.5 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound represented by formula (Ia). .
  • the amount of the base used in this reaction is usually 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound represented by the formula (Ia).
  • the reaction temperature for this reaction is usually ⁇ 30 to 180 ° C., preferably ⁇ 10 to 80 ° C.
  • the reaction time for this reaction is usually 10 minutes to 30 hours. After completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent, and the obtained organic layer is dried, concentrated, and subjected to operations such as purification by silica gel column chromatography.
  • the compound represented by -b) can be isolated.
  • the compound represented by the formula (IV) is a known compound or can be produced from a known compound.
  • the compound represented by the formula (Ic) can be produced by reacting the compound represented by the formula (Ia) with the compound represented by the formula (V).
  • R 10 has one or more atoms or groups selected from a C 1-12 alkyl group, a C 3-8 cycloalkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, and a group D.
  • C 6-10 aryl group (1 or more atoms or optionally C 6-10 aryl optionally having a group selected from group D) C 1-6 alkyl group, (C 3-8 cycloalkyl ) C 1-6 alkyl group, (C 1-6 alkoxy) C 1-6 alkyl group, (C 3-8 cycloalkoxy) C 1-6 alkyl group, (C 1-6 alkylthio) C 1-6 alkyl group , (C 1-6 alkylsulfinyl) C 1-6 alkyl group, (C 1-6 alkylsulfonyl) C 1-6 alkyl group, (may have one or more atoms or groups selected from group D) C 6-10 aryloxy C 1-12 alkyl group, (which may have one or more atoms or groups selected from Group D C 6-10 arylthio) C 1-12 alkyl group, one or more atoms selected from ⁇ (D group Or a C 6-10 aryl which may have a group selected from group
  • This reaction is usually performed in a solvent.
  • the solvent that can be used include aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, dioxane, THF, and dimethoxyethane; amides such as DMF; sulfoxides such as DMSO; Nitriles; ketones such as acetone or a mixed solvent thereof.
  • This reaction can also use a base.
  • the base used include inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride; and organic bases such as triethylamine, pyridine and 1,8-diazabicyclo [5.4.0] -7-undecene.
  • the amount of the base used in this reaction is usually 0.5 to 10 molar equivalents relative to the compound represented by the formula (Ia).
  • the amount of the compound represented by the formula (V) to be used is generally 1 to 20 molar equivalents relative to the compound represented by the formula (Ia).
  • the reaction temperature of this reaction is usually ⁇ 30 to 180 ° C.
  • the reaction time for this reaction is usually 10 minutes to 30 hours. After completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent, and the obtained organic layer is dried, concentrated, and subjected to operations such as purification by silica gel column chromatography.
  • the compound represented by -c) can be isolated.
  • the compound represented by the formula (V) is a known compound or can be produced from a known compound.
  • Each compound produced by the above production methods 1 to 3 may be isolated and purified by other known means such as methods such as phase transfer, crystallization, recrystallization, and chromatography. is there.
  • a method for producing an intermediate of the compound of the present invention will be described as a reference production method.
  • Reference manufacturing method 1 The compound represented by the formula (II) can be produced, for example, by reacting the compound represented by the formula (VI) with an acid.
  • R 15 represents a C 1-6 alkyl group or a benzyl group
  • R 16 represents hydrogen, a C 1-6 alkyl group or a benzyl group
  • R 1 , R 2 , R 3 , R 4 and R 5 represents the same meaning as described above.
  • As an acid used for this reaction hydrochloric acid or hydrobromic acid is mentioned, for example.
  • the amount of acid used in this reaction is usually 1 to 20 molar equivalents relative to the compound represented by formula (VI).
  • This reaction is carried out without solvent or in a solvent.
  • the solvent that can be used include organic acids such as acetic acid and propionic acid, water, and mixed solvents thereof.
  • the reaction temperature of this reaction is usually 30 to 180 ° C, preferably 50 to 130 ° C.
  • the reaction time for this reaction is usually 10 minutes to 30 hours.
  • the reaction mixture is mixed with water and extracted with an organic solvent, and the obtained organic layer is dried, concentrated, and subjected to operations such as purification by silica gel column chromatography. ) Can be isolated.
  • the compound represented by the formula (VI) is a known compound or can be produced from a known compound. For example, it can be produced according to the method described in EP2204366A or WO2009 / 035150.
  • the compound represented by the formula (VI-a) is obtained by, for example, reacting the compound represented by the formula (VII) with the compound represented by the formula (VIII) in the presence of a catalyst and a base.
  • a catalyst and a base can be manufactured.
  • X 2 , R 1 , R 2 , R 3 , R 4 , R 5 and R 15 represent the same meaning as described above.
  • This reaction is usually performed in a solvent.
  • solvents examples include aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, dioxane, THF and dimethoxyethane; ketones such as acetone and methyl ethyl ketone. Amides such as DMF; sulfoxides such as DMSO; water or a mixed solvent thereof is used.
  • inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, cesium carbonate, potassium phosphate, are mentioned, for example.
  • the amount of the base used is usually 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound represented by the formula (VII).
  • the catalyst used in this reaction include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium, and tris (dibenzylideneacetone) dipalladium.
  • the amount of the catalyst used is usually 0.001 to 0.5 molar equivalent, preferably 0.01 to 0.2 molar equivalent, relative to the compound represented by the formula (VII).
  • a ligand can also be added to this reaction.
  • Examples of the ligand used include 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl.
  • the amount of the ligand used is usually 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, relative to the compound represented by the formula (VII).
  • the amount of the compound represented by formula (VIII) used in this reaction is usually 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound represented by formula (VII). .
  • the reaction temperature of this reaction is usually 0 to 180 ° C., preferably 30 to 150 ° C.
  • the reaction time for this reaction is usually 10 minutes to 100 hours.
  • the compound represented by -a) can be isolated.
  • the compound represented by the formula (VIII) is a known compound or can be produced from a known compound.
  • the compound represented by the formula (VII) is a known compound or can be produced from a known compound. For example, it can be produced according to a method described in Journal of Heterocyclic Chemistry (J. Heterocycl. Chem.), Vol. 33, pages 1579 to 1582 (1996), or a method analogous thereto.
  • Reference manufacturing method 3 The compound represented by the formula (XV) in which R 2 is O—R 17 and X 2 is chlorine among the compounds represented by the formula (VII) can be produced, for example, by the following reaction scheme.
  • X 3 is a C 1-3 alkylsulfonyloxy group (for example, methylsulfonyloxy group, trifluoromethylsulfonyloxy group, etc.) optionally having chlorine, bromine, iodine, halogen, benzenesulfonyl group Or a p-toluenesulfonyl group
  • R 17 is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 3-8 cycloalkyl group, a (C 3-8 cycloalkyl) C 1-6 alkyl group, (C 1-6 alkylthio) C 1-6 alkyl group, (C 1-6 alkoxy) C 1-6 alkyl group, C 3-6
  • the compound represented by the formula (XI) can be produced by reacting the compound represented by the formula (IX) with the compound represented by the formula (X).
  • This reaction is a dehydration condensation reaction between maleic anhydride and a hydrazine compound, and can be performed under known conditions. For example, it can be produced according to the method described in US7816357B.
  • a compound represented by the formula (XIII) can be produced by reacting a compound represented by the formula (XI) with a compound represented by the formula (XII) in the presence of a base. This reaction can be performed under known conditions. For example, it can be produced according to the method described in WO2012 / 091156.
  • the compound represented by the formula (XV) can be produced by reacting the compound represented by the formula (XIII) with the compound represented by the formula (XIV) in the presence of a base.
  • This reaction is usually performed in a solvent.
  • solvents include alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, dioxane, THF and dimethoxyethane; amides such as DMF; sulfoxides such as DMSO or a mixed solvent thereof. It is done.
  • the base used in this reaction include sodium methoxide, potassium tert-butoxide, sodium hydride and the like.
  • the amount of the base used in this reaction is usually 0.5 to 10 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound represented by the formula (XIII).
  • the reaction temperature of this reaction is usually ⁇ 30 to 100 ° C.
  • the reaction time for this reaction is usually 10 minutes to 50 hours. After completion of this reaction, for example, the reaction mixture is mixed with water and extracted with an organic solvent, and the resulting organic layer is dried, concentrated, etc., to isolate the compound represented by the formula (XV). can do.
  • G is hydrogen
  • A is a phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2- Methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-nitrophenyl group, 3-nitrophenyl Group, 4-nitrophenyl group, 2-cyanophenyl
  • A is a 4-trifluoromethylphenyl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group, dimethylaminocarbonyl group, dimethylamin
  • A is a 2-fluoro-4-cyanophenyl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group, di
  • A is a 2-chloro-4-trifluoromethylphenyl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl
  • A is a 5-trifluoromethylpyridin-2-yl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group
  • A is a 2-fluoro-5-trifluoromethylpyridin-2-yl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylamin
  • A is a 2-chloro-5-trifluoromethylpyridin-2-yl group
  • G is acetyl, trifluoroacetyl, propionyl, butyryl, isobutyryl, isovaleryl, pivaloyl, 2-methylbutyryl, 3-methylbutyryl, 2,2-dimethylbutyryl, 3,3-dimethylbutyryl Ryl group, valeryl group, 2-methylvaleryl group, 2-ethylvaleryl group, 2-propylvaleryl group, hexanoyl group, 2-methylhexanoyl group, 2-ethylhexanoyl group, phenylacetyl group, 3-phenylpropionyl group, Methoxyacetyl group, ethoxyacetyl group, propoxyacetyl group, 3-methoxypropionyl group, 3-ethoxypropionyl group, 3-methoxy-2-methylpro
  • A is a 6-chloroquinoxalin-2-yl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group,
  • A is a 6-chlorobenzoxazol-2-yl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group
  • A is a benzothiazol-2-yl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group, dimethyla
  • A is a 6-chlorobenzothiazol-2-yl group
  • G is acetyl group, trifluoroacetyl group, propionyl group, butyryl group, isobutyryl group, isovaleryl group, pivaloyl group, 2,2-dimethylbutyryl group, 3,3-dimethylbutyryl group, cyclopropylcarbonyl group, cyclobutyl Carbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group, benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, phenylacetyl group, methoxycarbonyl group, ethoxycarbonyl group, isopropoxycarbonyl group, tert -Butoxycarbonyl group, phenoxycarbonyl group, allyloxycarbonyl group, dimethylaminocarbonyl group
  • Production Example 8 4- (2-Ethyl-4- (6-chloroquinoxalin-2-yloxy) phenyl)-, which is carried out according to Preparation Example 1, using 2,6-dichloroquinoxaline instead of 3,4-difluorobenzonitrile 2,6-dimethyl-5-hydroxy-3 (2H) -pyridazinone (compound (I-8)) was obtained.
  • Production Example 13 A production example using 4- (2-ethyl-4-hydroxyphenyl) -2-methyl-6-methoxy-5-hydroxy-3 (2H) -pyridazinone (compound II-3) instead of compound II-1 7, 4- (2-ethyl-4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl) -2-methyl-6-methoxy-5-hydroxy-3 (2H) -Pyridazinone (compound (I-13)) was obtained.
  • Reference Examples 1 to 3 show production examples of the compound represented by the formula (II).
  • Reference example 1 Synthesis of compound (II-1)
  • Reference Example 1-1 Synthesis of 4-bromo-3-ethylphenol 69.27 g of pyridinium bromide perbromide was added to a solution of 25.2 g of 3-ethylphenol in 300 ml of chloroform, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with water (twice), washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • Reference example 2 Synthesis of compound (II-2) Reference Example 2-1 Synthesis of 4- (2-methyl-4-benzyloxyphenyl) -2,6-dimethyl-5-methoxy-3 (2H) -pyridazinone Instead of 4-benzyloxy-2-ethylphenylboronic acid, 4-benzyloxy-2-methylphenylboronic acid was used and 4- (2-methyl-4-benzyloxyphenyl) was used according to Reference Example 1-4. -2,6-Dimethyl-5-methoxy-3 (2H) -pyridazinone was obtained.
  • reaction mixture was stirred at room temperature overnight, water was added, and the mixture was extracted twice with MTBE, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • a solution of the residue in 15 ml of anhydrous THF was added to a solution of 5.83 g of potassium t-butoxide and 20 ml of anhydrous THF at 35 to 40 ° C.
  • the reaction mixture was stirred at room temperature for 1 hour, 50 ml of 2N hydrochloric acid was added, extracted twice with MTBE, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • the residue was purified by silica gel column chromatography to obtain 1.41 g of the desired product.
  • Formulation Example 2 Granule Compound (I-1) 1.5% by weight 2% by weight sodium lignin sulfonate Talc 40% by weight Bentonite 56.5% by weight , Mixed with water, granulated and dried to obtain granules. In place of compound (I-1), compound (I-2) to compound (I-13), compound compound (I-14-1) to compound (I-14-71), compound (I- 15-1) to granule (I-15-2).
  • Formulation Example 3 Flowable compound Compound (I-1) 10% by weight 35% by weight of white carbon containing 50% by weight of polyoxyethylene alkyl ether sulfate ammonium salt 55% by weight of water Are mixed and finely pulverized by a wet pulverization method to obtain a flowable agent. In place of compound (I-1), compound (I-2) to compound (I-13), compound compound (I-14-1) to compound (I-14-71), compound (I- 15-1) to each flowable agent of compound (I-15-2) is obtained.
  • Test Example 1 Post-emergence post-emergence treatment test A plastic cup having a diameter of 8 cm and a depth of 6.5 cm is filled with a commercial seedling culture soil. Cultivated for a predetermined period. When the plant grew to the 1st to 2nd leaf stage, a drug diluent containing the compound of the present invention was uniformly sprayed over the whole plant at a predetermined treatment dose.
  • the drug diluent is prepared by dissolving a predetermined amount of the compound of the present invention in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water. Prepared.
  • Test Example 2 Field Germination Pretreatment Test A plastic cup having a diameter of 8 cm and a depth of 6.5 cm was filled with steam-sterilized field soil, seeded with wheat and covered with about 0.5 cm of soil. Subsequently, the chemical
  • the drug diluent was prepared by the same method as in Test Example 1. Plants after chemical treatment were cultivated in a greenhouse, and after 3 weeks of treatment, the effect of controlling wheat was observed and evaluated, and the results were shown in 11 stages of 0 to 10 as in Test Example 1. Similarly, other compounds of the present invention were also tested.
  • Test Example 3 Herbicidal Effect Test on Paddy Weeds
  • a plastic cup having a diameter of 9 cm and a depth of 10 cm filled with steam-sterilized soil was seeded with Tainubies and cultivated in a greenhouse to a predetermined growth stage (one leaf stage).
  • the drug diluted solution containing the compound of the present invention was subjected to inundated soil treatment at a predetermined treatment chemical amount.
  • the drug diluent is prepared by dissolving a predetermined amount of the compound of the present invention in an acetone solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluting with deionized water.
  • Test Example 4 Herbicidal effect test on paddy weeds A plastic cup having a diameter of 9 cm and a depth of 10 cm filled with steam-sterilized soil was sown and cultivated in a greenhouse until a predetermined growth stage (one leaf stage). After adjusting the inundation depth to 0 cm, the drug diluted solution containing the compound of the present invention was treated with foliage at a predetermined treatment dose. In the drug dilution solution, a predetermined amount of the compound of the present invention is dissolved in a dimethylformamide solution (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.) and diluted with deionized water. It was prepared by.
  • Tween 20 polyoxyethylene sorbitan fatty acid ester, manufactured by MP Biomedicals, Inc.
  • Comparative Test Example 1 According to the method described in Test Example 3 for herbicidal effect on paddy weeds, a herbicidal effect test on paddy weeds was conducted using Compound (I-2) and Comparative Compound 1. The results are shown in Table 2.
  • Comparative compound 1 is described as a compound having herbicidal activity in WO2009086041 Al Table 5CA (pages 67-68).
  • the compound of the present invention has a weed control effect.

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Abstract

La présente invention concerne un composé pyridazinone représenté par la formule (I) qui est un composé utile comme principe actif pour un herbicide. (Dans la formule, R1, R2 et R3 représentent indépendamment un groupe alkyle en C1-6 ou analogue; R4 et R5 représentent indépendamment un atome d'hydrogène ou analogue; A représente un groupe aryle cyclique condensé monocyclique ou bicyclique ou analogue; et G représente un atome d'hydrogène ou analogue.)
PCT/JP2014/052366 2013-01-30 2014-01-27 Composé pyridazinone et herbicide comprenant celui-ci WO2014119770A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014207601A1 (fr) * 2013-06-27 2014-12-31 Pfizer Inc. Composés hétéro-aromatiques et leur utilisation en tant que ligands d1 de la dopamine
WO2016008816A1 (fr) * 2014-07-17 2016-01-21 Syngenta Participations Ag Dérivés herbicides de pyridazinone
WO2017170759A1 (fr) 2016-03-30 2017-10-05 石原産業株式会社 Constituant type-pyridazinone ou son sel, et herbicide le comprenant
JP2018515470A (ja) * 2015-04-30 2018-06-14 シンジェンタ パーティシペーションズ アーゲー 除草性化合物
WO2019065283A1 (fr) * 2017-09-27 2019-04-04 石原産業株式会社 Composé de pyridazinone ou sel de celui-ci, et herbicide le contenant

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JP2009084276A (ja) * 2007-09-14 2009-04-23 Sumitomo Chemical Co Ltd ピリダジノン化合物及びそれを含有する除草剤
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