WO2022092084A1 - Dérivé hétérocyclique fusionné et herbicide le contenant en tant que principe actif - Google Patents

Dérivé hétérocyclique fusionné et herbicide le contenant en tant que principe actif Download PDF

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WO2022092084A1
WO2022092084A1 PCT/JP2021/039485 JP2021039485W WO2022092084A1 WO 2022092084 A1 WO2022092084 A1 WO 2022092084A1 JP 2021039485 W JP2021039485 W JP 2021039485W WO 2022092084 A1 WO2022092084 A1 WO 2022092084A1
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mono
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PCT/JP2021/039485
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幸浩 榎本
和貴 野城
貴史 塩澤
崇史 佐藤
貴章 平井
愛理 太田
匡毅 羽根
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クミアイ化学工業株式会社
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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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • 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
    • 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
    • C07D403/14—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 three or more hetero rings
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings

Definitions

  • the present invention relates to a novel condensed heterocyclic derivative or an agriculturally acceptable salt thereof, and a herbicide containing the derivative as an active ingredient.
  • Patent Documents 1 and 2 describe pyrimidinyloxy-condensed heterocyclic derivatives having a herbicidal effect.
  • Patent Document 3 describes a pyrimidinyloxy or a pyridinyloxy-condensed heterocyclic derivative having a Kv3 channel inhibitory activity.
  • Patent Document 4 describes a 7- (pyridin-2-yloxy) -1H-benzimidazole derivative having an antifungal effect.
  • Patent Document 5 describes a 7- (pyridin-2-yloxy) -1H-indazole derivative having a tyrosine kinase inhibitory activity.
  • Patent Document 6 describes a 7- (pyridin-2-yloxy) -1H-indole derivative having a collagen synthesis inhibitory activity.
  • Patent Documents 7 and 8 describe 7- (pyridin-2-yloxy) indoline-2-one derivatives having bromodomain inhibitory activity.
  • Patent Documents 1 and 2 are not sufficient in terms of herbicidal effect and the like.
  • Patent Document 3 the 5-position of the pyrimidine ring or the pyridine ring is limited to the 2,5-dioxoimidazolidine-1-yl group, and Patent Document 3 does not pay attention to the herbicidal effect. ..
  • Patent Document 4 In the compound described in Patent Document 4, the 5-position of the pyridine ring is limited to the formimide group, and Patent Document 4 does not pay attention to the herbicidal effect.
  • Patent Document 6 the 5-position of the pyridine ring is limited to a benzamide group or the like, and Patent Document 6 does not pay attention to the herbicidal effect.
  • Patent Documents 7 and 8 are limited to derivatives in which the 5-position of the indolin-2-one ring is substituted with a 1-phenyl-1H-pyrazole-5-yl group, a phenylsulfonamide group, or the like. , Patent Documents 7 and 8 do not pay attention to the herbicidal effect.
  • the present invention has been made in view of the above circumstances, and an object thereof is to produce various weeds generated in upland fields, orchards, paddy fields, non-agricultural lands, etc. without causing chemical damage to useful plants. It is an object of the present invention to provide a compound having a herbicidal activity that can be controlled with a low dose, and a herbicide containing the compound.
  • the present inventors synthesized a large number of condensed heterocyclic derivatives and diligently investigated their herbicidal activity and usefulness.
  • the fused heterocyclic derivative represented by the following general formula [I] hereinafter referred to as “the compound of the present invention”
  • various weeds can be controlled for a long period of time. It was found that a remarkable herbicidal effect was exhibited without causing chemical damage to plants, and further research was continued to complete the present invention.
  • Q indicates Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 or Q-8.
  • R 1 is a hydrogen atom, a C 1 to C 6 alkyl group (the group may be mono-substituted or poly-substituted by R 8 ), a C 2 -C 6 alkenyl group (the group may be mono-substituted or poly-substituted by R 8 ). Substituted) , C2 - C6 alkynyl group (the group may be mono-substituted or poly - substituted with R8), C3 - C6 cycloalkyl group (the group may be mono-substituted or poly-substituted with R8).
  • phenyl group (the group may be mono- or poly-substituted by R 9 ) or a heteroaryl group (the group may be mono- or poly-substituted by R 9 ).
  • Piperidine-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R 9 ), hydroxy group, C 1 to C 6 alkoxy group, C 3 to C 6 alkenyloxy group, C 3 to C 6 alkynyloxy group, C 1 to C 6 haloalkoxy group, C 3 to C 6 cycloalkoxy group, C 3 to C 6 halocycloalkoxy group, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy group, phenoxy group (the group may be mono-substituted or poly-substituted with R 9 ), phenyl C 1 to C 6 alkoxy group (the phenyl group is R 9 ).
  • R 9 May be mono-substituted or poly-substituted with R 9 ), a phenylsulfonyl group (the group may be mono- or poly - substituted with R 9 ), an amino group, a C1-6 alkylamino group (the amino).
  • the group may be substituted with R 12 ), a C 1 to C 6 haloalkylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkylcarbonylamino group (the amino group may be R 12).
  • C 1 to C 6 haloalkylcarbonylamino groups (the amino groups may be substituted by R12 ), C3 to C6 cycloalkylcarbonylamino groups (the amino groups may be R12 ). (May be substituted with R 9 ), phenylcarbonylamino group (the phenyl group may be mono-substituted or poly-substituted with R 9, and the amino group may be substituted with R 12 ), C 1 to C 6 alkoxy.
  • a carbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 haloalkoxycarbonyl amino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkylamino.
  • a carbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 haloalkylaminocarbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkylsulfonyl.
  • Amino group (the amino group may be substituted with R 12 ), C 1 to C 6 haloalkylsulfonylamino group (the amino group may be substituted with R 12 ), C 3 to C 6 cycloalkylsulfonylamino.
  • a group (the amino group may be substituted with R 12 ), a phenylsulfonyl amino group (the phenyl group may be mono-substituted or poly-substituted with R 9 , and the amino group may be substituted with R 12 ).
  • R 9 is a halogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 ⁇ C 6 halocycloalkyl group, formyl group, hydroxy group, C 1 ⁇ C 6 alkoxy group, C 1 ⁇ C 6 haloalkoxy group, thiol group, C 1 ⁇ C 6 alkylthio group, C 1 ⁇ C 6 alkyl sulfinyl group , C 1 to C 6 alkylsulfonyl groups, C 1 to C 6 haloalkylthio groups, C1 to C6 haloalkylsulfinyl groups, C1 to C6 haloalkylsulfonyl groups, cyan
  • R 10 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, phenyl group. (The group may be mono-substituted or poly-substituted with R 9 ) or a heteroaryl group (the group may be mono- or poly-substituted with R 9 ).
  • R 11 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group or C 3 Representing a ⁇ C6 halocycloalkyl group
  • R 12 is a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 1 to C 6 haloalkyl group, a C 3 to C 6 cycloalkyl group, and a C 3 to C 6 .
  • Halocycloalkyl group C3 to C6 cycloalkyl C1 to C6 alkyl group, C1 to C 6alkoxy C1 to C6 alkyl group, C1 to C 6 haloalkoxy C1 to C6 alkyl group, cyano C 1 to C 6 alkyl groups, C 1 to C 6 alkyl carbonyl groups, C 1 to C 6 haloalkyl carbonyl groups, C 1 to C 6 alkoxycarbonyl groups, C 1 to C 6 halo alkoxycarbonyl groups, C 1 to C 6 An alkylaminocarbonyl group, a C1 to C6 haloalkylaminocarbonyl group or a benzoyl group (the group may be mono - substituted or poly - substituted by R9) is shown.
  • R 2 is a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, a C 1 to C 6 haloalkyl group, and a C 3 to C 6 cycloalkyl group.
  • C1 to C6 haloalkylaminocarbonyl group (the amino group may be substituted by R12 ), hydroxy group, C1 to C6 alkoxy group , C3 to C6 alkenyloxy group. , C 3 to C 6 alkynyloxy groups, C 1 to C 6 haloalkoxy groups, C 3 to C 6 cycloalkoxy groups, C 3 to C 6 halocycloalkoxy groups, C 3 to C 6 cycloalkyls C 1 to C 6 Alkoxy groups, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy groups, phenyl C 1 to C 6 alkoxy groups (the phenyl groups may be mono-substituted or poly-substituted by R9), heteroaryloxy groups.
  • the group may be mono-substituted or poly-substituted with R 9 ), C 1 to C 6 alkylthio groups, C 1 to C 6 alkyl sulfinyl groups, C 1 to C 6 alkyl sulfonyl groups, C 1 to C 6 halos.
  • a carbonylamino group (the amino group may be substituted with R 12 ), a C 3 to C 6 cycloalkylcarbonyl amino group (the amino group may be substituted with R 12 ), a C 1 to C 6 alkoxycarbonyl.
  • Amino group (the amino group is R 12 may be substituted), C 1 to C 6 alkylsulfonylamino groups (the amino groups may be substituted by R 12 ), C 1 to C 6 haloalkylsulfonyl amino groups (the amino groups may be substituted by R 12 ).
  • C 3 - C6 cycloalkylsulfonylamino group (the amino group may be substituted with R 12 ), phenyl group (the group may be mono-substituted or poly-substituted with R 9 ). ), Heteroaryl group (the group may be mono-substituted or poly-substituted by R9), cyano group or nitro group.
  • R 3 is a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkoxy group, a C 2 to C 6 alkoxyyl group , a C 1 to C 6 haloalkyl group, and a C 3 to C 6 cycloalkyl group.
  • C 3 to C 6 halocycloalkyl groups C 1 to C 6 alkoxy C 1 to C 6 alkyl groups, C 1 to C 6 haloalkoxy C 1 to C 6 alkyl groups, C 1 to C 6 alkylthios C 1 to C 6 Alkoxy Group, C 1 to C 6 Alkoxy Sulfinyl C 1 to C 6 Alkoxy Group, C 1 to C 6 Alkoxysulfonyl C 1 to C 6 Alkoxy Group, C 1 to C 6 Haloalkylthio C 1 to C 6 Alkoxy Group, C 1 to C 6 haloalkylsulfinyl C 1 to C 6 alkyl groups, C 1 to C 6 haloalkylsulfonyl C 1 to C 6 alkyl groups, cyano C 1 to C 6 alkyl groups, formyl groups, C 1 to C 6 alkyl carbonyl groups, C 1 to C 6 haloalkyl carbonyl group, C 3 to C 6 cycl
  • Hydroxyl group C1 to C6 alkoxy group, C3 to C6 alkoxyoxy group , C3 to C6 alkynyloxy group , C1 to C6 haloalkoxy group , C3 to C 6 cycloalkoxy groups, C 3 to C 6 halocycloalkoxy groups, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy groups, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy groups, phenyl C 1 to C 6 alkoxy group (the phenyl group may be mono-substituted or poly-substituted with R 9 ), heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), C 1 -C 6 Alkoxythio groups , C1 to C6 alkylsulfinyl groups, C1 to C6 alkylsulfonyl groups, C1 to C6 halo
  • R4 is independently a halogen atom, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, hydroxy group, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, cyano group or nitro.
  • m represents an integer of 0, 1, 2 or 3
  • Y represents an oxygen atom or a sulfur atom.
  • R 5 independently contains a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 3 to C 6 cycloalkyl group, a C 3 to C 6 halocycloalkyl group, and a hydroxy group. , C 1 to C 6 alkoxy groups, C 1 to C 6 haloalkoxy groups, heteroaryloxy groups (the groups may be mono- or poly-substituted with R 9 ), tri (C 1 to C 6 alkyl) silyloxy.
  • It represents a group or a cyano group, and the two R5s may be combined to form an oxo group ( O), or a C1 to C6 alkoxyimino group, and the two R5s are bound to each other.
  • a C1 to C6 alkoxyimino group and the two R5s are bound to each other.
  • Select from a 3- to 6-membered carbocycle, or a nitrogen atom, an oxygen atom, and a sulfur atom (the sulfur atom may be substituted with one or two oxo groups ( O)) together with these bonded carbon atoms. It may form a 3- to 6-membered heterocycle having 1 to 4 heteroatoms to be formed.
  • R 6 is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 ⁇ C 6 halocycloalkyl group, C 3 ⁇ C 6 cycloalkyl C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 alkoxy C 1 ⁇ C 6 alkyl group, C 1 ⁇ C 6 haloalkoxy C 1 ⁇ C 6 alkyl Group, cyano C 1 to C 6 alkyl group, C 1 to C 6 alkyl carbonyl group, C 1 to C 6 alkoxycarbonyl group or C 1 to C 6 alkyl sulfonyl group.
  • R 7 is a halogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 ⁇ C 6 halocycloalkyl group, hydroxy group, C 1 ⁇ C 6 alkoxy group, C 1 ⁇ C 6 haloalkoxy group, C 1 ⁇ C 6 alkylthio group, C 1 ⁇ C 6 alkyl sulfinyl group, C 1 ⁇ C 6 Indicates an alkylsulfonyl group, a C1 to C6 haloalkylthio group, a C1 to C6 haloalkylsulfinyl group, a C1 to C6 haloalkylsulfonyl group, a cyano group or a nitro group.
  • Z represents an oxygen atom or a sulfur atom.
  • A indicates N or CR 13 .
  • R 13 represents a hydrogen atom, a halogen atom or a cyano group] Condensed heterocyclic derivative represented by, or an agriculturally acceptable salt thereof.
  • R 1 is a hydrogen atom, a C 1 to C 6 alkyl group (the group may be mono-substituted or poly-substituted by R 8 ), a C 2 -C 6 alkenyl group (the group may be mono-substituted or poly-substituted by R 8).
  • the group may be mono-substituted or poly-substituted with R 8 ), a C2 - C6 alkynyl group (the group may be mono- or poly-substituted with R 8 ), a phenyl group (the group may be R 9 ).
  • R 8 is a halogen atom, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group, C 3 to C 6 halocycloalkyl group, benzoyl group (the group is mono-substituted or poly-substituted by R 9 ).
  • C 1 to C 6 alkoxycarbonyl group C 1 to C 6 alkoxy group, C 1 to C 6 alkoxy group, C 1 to C 6 haloalkoxy group, C 3 to C 6 cycloalkoxy group, C 3 to C 6 halocycloalkoxy group, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group, phenoxy group (the group may be mono-substituted or poly-substituted with R 9 ), C 1 to C 6 haloalkyl thio group, C 1 to C 6 haloalkyl sulfinyl.
  • Phenylsulfonyl group (the group may be mono-substituted or poly-substituted with R 9 ), phenylsulfonyl amino group (the phenyl group may be mono-substituted or poly-substituted with R 9 ), the amino group may be R (May be substituted with 12 ), phenyl group (the group may be mono-substituted or poly-substituted with R 9 ), heteroaryl group (the group may be mono- or poly-substituted with R 9 ),.
  • a heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), a heterocycloalkyl group (the group may be mono-substituted or poly-substituted with R 9 ), a cyano group or a thiocyanato group.
  • R 9 represents a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a formyl group, a C 1 to C 6 alkoxy group, a C 1 to C 6 haloalkoxy group, a cyano group or a nitro group.
  • R 10 indicates a hydrogen atom and represents a hydrogen atom.
  • R 11 represents a C 1 to C 6 alkyl group.
  • R 12 represents a C 1 to C 6 alkyl group.
  • R 2 represents a hydrogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 1 to C 6 alkoxycarbonyl group, an aminocarbonyl group or a cyano group.
  • R 3 is a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 1 to C 6 haloalkyl group, a C 3 to C 6 cycloalkyl group, and a C 1 to C 6 alkoxy C.
  • C 1 to C 6 alkylthio groups C 1 to C 6 alkyl sulfinyl groups, C 1 to C 6 alkyl sulfonyl groups, C 1 to C 6 alkyl amino groups (the amino groups may be substituted with R 12 ).
  • a phenyl group (the group may be mono- or poly-substituted by R9 ) or a cyano group.
  • R 4 represents a halogen atom or a C 1 to C 6 alkyl group.
  • m represents an integer of 0 or 1 and represents Y represents an oxygen atom or a sulfur atom.
  • R 5 is independently a halogen atom, C 1 to C 6 alkyl group, C 1 to C 6 haloalkyl group, hydroxy group, C 1 to C 6 alkoxy group, C 1 to C 6 halo alkoxy group, heteroaryloxy group.
  • R 6 represents a C 1 to C 6 alkyl group or a C 1 to C 6 haloalkyl group.
  • R 7 represents a halogen atom, a C1 to C6 haloalkyl group or a cyano group.
  • Z is the condensed heterocyclic derivative according to (1) above, which represents an oxygen atom, or an agriculturally acceptable salt thereof.
  • Q represents Q-1, Q-2, Q-3 or Q-4.
  • R 1 represents a C 1 to C 6 alkyl group (the group may be mono- or poly-substituted by R 8 ).
  • R 8 is a C 3 to C 6 cycloalkyl group, a C 3 to C 6 halocycloalkyl group, a benzoyl group (the group may be mono-substituted or poly-substituted by R 9 ), C 1 to C 6 alkoxycarbonyl.
  • phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R 9 ), phenylsulfonyl group (the group may be mono- or poly-substituted with R 9 ), phenylsulfonylamino group (may be).
  • the phenyl group may be mono-substituted or poly-substituted with R 9
  • the amino group may be substituted with R 12
  • a phenyl group (the group may be mono- or poly-substituted with R 9 ).
  • Heteroaryl group (the group may be mono-substituted or poly-substituted with R 9 ), heteroaryloxy group (the group may be mono-substituted or poly-substituted with R 9 ), heterocycloalkyl group (the group may be mono-substituted or poly-substituted).
  • the group may be mono-substituted or poly-substituted with R9), the fused heterocyclic derivative according to ( 2 ) above, which exhibits a cyano group or a thiocyanato group, or an agriculturally acceptable salt thereof.
  • R 8 is a phenyl group (the group may be mono-substituted or poly-substituted by R 9 ), a heteroaryl group (the group may be mono-substituted or poly-substituted by R 9 ).
  • Q is the condensed heterocyclic derivative according to (3) above, which represents Q-1, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (3) or (4) above, which represents Q-2, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (3) or (4) above, which represents Q-3, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (3) above, which represents Q-4, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-5, Q-6, Q-7 or Q-8, or its agriculture. Above acceptable salt.
  • Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-5, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-6, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (1) or (2) above, which represents Q-7, or an agriculturally acceptable salt thereof.
  • Q is the condensed heterocyclic derivative according to (1) above, which is represented by Q-8, or an agriculturally acceptable salt thereof.
  • the condensed heterocyclic derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof can control various weeds generated in upland fields, paddy fields, orchards, and non-agricultural lands, and is more useful. It has excellent action and effect as a pesticide, such as showing high safety to plants and the like.
  • halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • notations such as “C 1 to C 6 " indicate that the number of carbon atoms of the subsequent substituent is 1 to 6 in this case.
  • C 1 to C 6 alkyl group refers to a linear or branched alkyl group having 1 to 6 carbon atoms, unless otherwise specified, for example, methyl, ethyl, n-propyl, and the like.
  • the " C2 to C6 alkenyl group” refers to a linear or branched alkenyl group having 2 to 6 carbon atoms, and is, for example, vinyl, 1-propenyl, isopropenyl, for example, unless otherwise specified.
  • the " C2 to C6 alkynyl group” refers to a linear or branched alkynyl group having 2 to 6 carbon atoms, unless otherwise specified, for example, ethynyl, 1-propynyl, 2-.
  • C 3 to C 6 cycloalkyl group refers to a cycloalkyl group having 3 to 6 carbon atoms unless otherwise specified, and examples thereof include groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. be able to.
  • heteroaryl group is a 5-membered or 6-membered single having 1 to 6 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom, unless otherwise specified.
  • a ring heterocycle for example, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, Oxazole-2-yl, Oxazole-4-yl, Oxazole-5-yl, Isoxazole-3-yl, Isoxazole-4-yl, Isoxazole-5-yl, Thiazole-2-yl, Thiazole-4-yl , Thiazole-5-yl, isothiazole-3-yl, isothiazole-4-yl, isothiazole-5-yl, imidazole-1-yl, imidazole-2-yl, imidazole-4-yl, pyrazole-1- Il, pyrazole-3-yl, pyrazole-4-yl, pyrazole-5-yl, 1,3,4-oxadiazole-2-yl,
  • C 1 to C 6 haloalkyl groups refers to linear or branched alkyl groups having 1 to 6 carbon atoms substituted with the same or different halogen atoms 1 to 13 unless otherwise specified.
  • haloalkyl groups eg, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1 -Fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1 -Chloroethyl, 2-chloroeth
  • C 3 to C 6 halocycloalkyl group refers to a cycloalkyl group having 3 to 6 carbon atoms substituted with the same or different halogen atoms of 1 to 11 unless otherwise specified.
  • examples thereof include groups such as cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl and the like.
  • the "C 1 to C 6 alkoxy group” means an (C 1 to C 6 alkyl) -O- group in which the alkyl moiety has the above meaning unless otherwise specified, and for example, methoxy, ethoxy, etc. n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethyl Groups such as propoxy, 1,2-dimethylpropoxy or n-hexyloxy can be mentioned.
  • C 3 to C 6 alkenyloxy group means an (C 3 to C 6 alkenyl) -O- group in which the alkenyl moiety has the above meaning unless otherwise specified, and for example, 2-propenyl.
  • Oxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 4-methyl-3-butenyloxy, 4-pentenyloxy or 5 -A group such as hexenyloxy can be mentioned.
  • the "C 3 to C 6 alkynyloxy group” means an (C 3 to C 6 alkynyl) -O- group in which the alkynyl moiety has the above meaning unless otherwise specified, and for example, 2-propynyl.
  • C 1 to C 6 haloalkoxy group means an (C 1 to C 6 haloalkyl) -O- group in which the haloalkyl moiety has the above meaning unless otherwise specified, and for example, difluoromethoxy, etc.
  • C 3 to C 6 cycloalkoxy group means an (C 3 to C 6 cycloalkyl) -O- group in which the cycloalkyl moiety has the above meaning unless otherwise specified, and for example, cyclo.
  • Groups such as propoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy can be mentioned.
  • the "C 3 to C 6 halocycloalkoxy group” indicates a (C 3 to C 6 halocycloalkyl) -O- group in which the halocycloalkyl moiety has the above meaning unless otherwise specified.
  • Groups such as cyclopentyloxy, 3,3-dichlorocyclopentyloxy, 4,4-difluorocyclohexyloxy or 4,4-dichlorocyclohexyloxy can be mentioned.
  • C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group means the cycloalkyl moiety as described above (C 3 to C 6 cycloalkyl)-(C 1 ) unless otherwise specified.
  • ⁇ C 6 alkyl) -O-group and examples thereof include groups such as cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, 2-cyclopropylethoxy, 2-cyclobutylethoxy or 2-cyclopentylethoxy.
  • C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy group means the above-mentioned meaning of the halocycloalkyl moiety unless otherwise specified (C 3 to C 6 halocycloalkyl). It shows (C 1 to C 6 alkyl) -O- groups and indicates, for example, (1-fluorocyclopropyl) methoxy, (2-fluorocyclopropyl) methoxy, (2,2-difluorocyclopropyl) methoxy, (2-chloro). Groups such as cyclopropyl) methoxy or (2,2-dichlorocyclopropyl) methoxy can be mentioned.
  • the "phenyl C 1 to C 6 alkoxy group” refers to a phenyl- (C 1 to C 6 alkyl) -O- group in which the alkyl moiety has the above meaning, unless otherwise specified, for example, phenyl.
  • Groups such as methoxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylpropoxy, 2-phenylbutoxy or 1-phenylpentoxy can be mentioned.
  • C 1 to C 6 alkylthio group means an (C 1 to C 6 alkyl) -S- group in which the alkyl moiety has the above meaning unless otherwise specified, and for example, methylthio, ethylthio, and the like.
  • Groups such as n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio can be mentioned.
  • groups such as methyl sulfonyl, ethyl sulfonyl, n-propyl sulfonyl, isopropyl sulfonyl, n-butyl sulfonyl, isobutyl sulfonyl, sec-butyl sulfonyl or tert-butyl sulfonyl can be mentioned.
  • C 1 to C 6 haloalkylthio group means a (C 1 to C 6 haloalkyl) -S- group in which the haloalkyl moiety has the above meaning unless otherwise specified, and for example, fluoromethylthio.
  • Difluoromethylsulfinyl trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, pentafluoroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl , Heptafluoropropylsulfinyl, heptafluoro-2-propylsulfinyl and the like.
  • difluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl or heptafluoro- Groups such as 2-propylsulfonyl and the like can be mentioned.
  • C 3 to C 6 cycloalkylthio group means a (C 3 to C 6 cycloalkyl) -S- group in which the cycloalkyl moiety has the above meaning unless otherwise specified, and for example, cyclo.
  • Groups such as propylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio can be mentioned.
  • examples thereof include groups such as cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl or cyclohexylsulfinyl.
  • a group such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, or cyclohexylsulfonyl can be mentioned.
  • C 3 to C 6 halocycloalkylthio group means a (C 3 to C 6 halocycloalkyl) -S- group in which the halocycloalkyl moiety has the above meaning unless otherwise specified.
  • groups such as 2,2-difluorocyclopropylthio, 2,2-dichlorocyclopropylthio, 3,3-difluorocyclobutylthio, 3,3-difluorocyclopentylthio or 4,4-difluorocyclohexylthio are mentioned. be able to.
  • -Indicating a group for example 2,2-difluorocyclopropylsulfinyl, 2,2-dichlorocyclopropylsulfinyl, 3,3-difluorocyclobutylsulfinyl, 3,3-difluorocyclopentylsulfinyl or 4,4-difluorocyclohexyl Groups such as sulfinyl can be mentioned.
  • Indicates a 2 -group eg, to 2,2-difluorocyclopropylsulfonyl, 2,2-dichlorocyclopropylsulfonyl, 3,3-difluorocyclobutylsulfonyl, 3,3-difluorocyclopentylsulfonyl or 4,4-difluorocyclo.
  • Groups such as xylsulfonyl can be mentioned.
  • C 3 to C 6 cycloalkyl C 1 to C 6 alkylthio groups means the cycloalkyl moiety and the alkyl moiety as described above (C 3 to C 6 cycloalkyl) unless otherwise specified.
  • (C 1 to C 6 alkyl) -S-groups eg cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylthio, 4-cyclopropylbutylthio, 5-cyclopropylpentylthio, cyclo.
  • Groups such as butylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio and the like can be mentioned.
  • C 3 to C 6 cycloalkyl C 1 to C 6 alkyl sulfinyl groups means the cycloalkyl moiety and the alkyl moiety as described above (C 3 to C 6 cycloalkyl) unless otherwise specified.
  • C 3 to C 6 cycloalkyl C 1 to C 6 alkyl sulfonyl groups means the cycloalkyl moiety and the alkyl moiety as described above (C 3 to C 6 cycloalkyl) unless otherwise specified.
  • C 3 to C 6 halocycloalkyl C 1 to C 6 alkylthio groups means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety unless otherwise specified (C 3 to C 6 halocyclo).
  • Alkyl)-(C 1 to C 6 alkyl) -S- groups for example 2,2-difluorocyclopropylmethylthio, 2,2-dichlorocyclopropylmethylthio, 2- (2,2-difluorocyclopropyl) ethylthio.
  • C 3 to C 6 halocycloalkyl C 1 to C 6 alkyl sulfinyl groups means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety (C 3 to C 6 halo) unless otherwise specified.
  • C 3 to C 6 halocycloalkyl C 1 to C 6 alkyl sulfonyl groups means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety unless otherwise specified (C 3 to C 6 halo).
  • Cycloalkyl)-(C 1 to C 6 alkyl) -S ( O) 2 -represents groups such as (1-fluorocyclopropyl) methylsulfonyl, (2-fluorocyclopropyl) methylsulfonyl, (2,2).
  • C 1 to C 6 alkylamino group means an (C 1 to C 6 alkyl) -NH- group in which the alkyl moiety has the above meaning unless otherwise specified, and for example, methylamino.
  • Groups such as ethylamino, n-propylamino, isopropylamino and the like can be mentioned.
  • the "C 1 to C 6 haloalkylamino group” means a (C 1 to C 6 haloalkyl) -NH- group in which the haloalkyl moiety has the above meaning unless otherwise specified, and for example, 2-fluoro.
  • examples thereof include groups such as acetylamino, propionylamino, butyrylamino or isobutyrylamino.
  • fluoroacetylamino difluoroacetylamino, trifluoroacetylamino, chloroacetylamino, trichloroacetylamino, tribromoacetylamino, 3,3,3-trifluoropropionylamino, pentafluoropropionylamino or 3,3- Groups such as difluoropropionylamino and the like can be mentioned.
  • -A group is shown, and examples thereof include groups such as cyclopropylcarbonylamino, cyclobutylcarbonylamino, cyclopentylcarbonylamino, and cyclohexylcarbonylamino.
  • examples thereof include groups such as methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino or isobutoxycarbonylamino.
  • the group indicates, for example, 2-fluoroethoxycarbonylamino, 2,2,2-trifluoroethoxycarbonylamino, 2,2,2-trichloroethoxycarbonylamino, pentafluoroethoxycarbonylamino, 3,3,3-trifluoro.
  • Groups such as propoxycarbonylamino or heptafluoro-2-propoxycarbonylamino can be mentioned.
  • -A group is shown, and examples thereof include groups such as methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino and tert-butylaminocarbonylamino.
  • -Indicates a group, for example 2-fluoroethylaminocarbonylamino, 2,2,2-trifluoroethylaminocarbonylamino, 2,2,2-trichloroethylaminocarbonylamino, pentafluoroethylaminocarbonylamino or 1,1 , 1,3,3,3-hexafluoro-2-propylaminocarbonylamino and the like can be mentioned.
  • a group such as methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino or tert-butylsulfonylamino can be mentioned.
  • Groups such as amino or 3,3,3-trifluoropropylsulfonylamino can be mentioned.
  • the "tri (C 1 to C 6 alkyl) silyl group” means a (C 1 to C 6 alkyl) 3 -Si- group in which the alkyl moiety has the above meaning unless otherwise specified, and 3
  • the alkyl groups may be the same or different from each other, and examples thereof include groups such as trimethylsilyl, triethylsilyl, triisopropylsilyl, dimethylisopropylsilyl and tert-butyldimethylsilyl.
  • 1,3-benzodioxolyl group is defined as, for example, 1,3-benzodioxole-4-yl or 1,3-benzodioxol-5-yl, unless otherwise specified. Etc. can be mentioned.
  • heteroaryloxy group means, unless otherwise specified, a (heteroaryl) -O-group in which the heteroaryl moiety has the above meaning, for example, (pyridin-2-yl) oxy, (pyridin-2-yl) oxy.
  • the "heterocycloalkyl group” indicates a 3- to 6-membered saturated heterocycle containing at least one atom selected from an oxygen atom, a nitrogen atom, and a sulfur atom in addition to a carbon atom, unless otherwise specified.
  • -Il or tetrahydropyran-4-yl and other groups can be mentioned.
  • C 3 to C 6 cycloalkyl C 1 to C 6 alkyl groups means the cycloalkyl moiety and the alkyl moiety as described above (C 3 to C 6 cycloalkyl) unless otherwise specified.
  • (C 1 to C 6 alkyl) -groups eg cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1- (cyclopropyl) ethyl, 2- (cyclopropyl) ethyl or 1- (cyclopropyl)
  • a group such as propyl can be mentioned.
  • C 1 to C 6 alkoxy C 1 to C 6 alkyl groups means the above-mentioned meanings of the alkoxy moiety and the alkyl moiety unless otherwise specified (C 1 to C 6 alkoxy)-(C 1 ).
  • C 1 to C 6 haloalkyl C 1 to C 6 alkyl groups means the above-mentioned meanings of the haloalkoxy moiety and the alkyl moiety (C 1 to C 6 haloalkyl) unless otherwise specified.
  • (C 1 to C 6 alkyl) -groups eg 2- (difluoromethoxy) ethyl, 2- (trifluoromethoxy) ethyl, 2- (2,2-difluoroethoxy) ethyl, 2- (2,2) , 2-trifluoroethoxy) ethyl, 2- (3,3-difluoropropioxy) ethyl, 2- (3,3,3-trifluoropropioxy) ethyl, 3- (difluoromethoxy) propyl, 3- (tri) Fluoromethoxy) propyl, 3- (2,2-difluoroethoxy) propyl, 3- (2,2,2-trifluoroethoxy) propyl, 3- (3,3-difluoropropioxy) propyl, 3- (3) Groups such as 3,3-trifluoropropioxy) propyl, 4- (trifluoromethoxy) butyl or 5- (trifluoromethoxy) penty
  • C 1 to C 6 alkyl thio C 1 to C 6 alkyl groups means the above-mentioned meanings of the alkyl thio moiety and the alkyl moiety unless otherwise specified (C 1 to C 6 alkyl thio)-(C 1 ).
  • ⁇ C 6 Alkyl -indicates a group, for example, methylthiomethyl, ethylthiomethyl, isopropylthiomethyl, 1-methylthioethyl, 2-methylthioethyl, 2-ethylthioethyl, 2-methylthiopropyl, 3-methylthiopropyl, 2 -Groups such as ethylthiopropyl or 3-ethylthiopropyl can be mentioned.
  • C 1 to C 6 alkyl sulfinyl C 1 to C 6 alkyl groups means the above-mentioned meanings of the alkyl sulfinyl moiety and the alkyl moiety unless otherwise specified (C 1 to C 6 alkyl sulfinyl)-.
  • C 1 to C 6 alkyl sulfonyl C 1 to C 6 alkyl groups means the above-mentioned meanings of the alkyl sulfonyl moiety and the alkyl moiety unless otherwise specified (C 1 to C 6 alkyl sulfonyl)-.
  • C 1 to C 6 haloalkylthio C 1 to C 6 alkyl groups means the above-mentioned meanings of the haloalkylthio moiety and the alkyl moiety unless otherwise specified (C 1 to C 6 haloalkylthio)-.
  • (C 1 to C 6 alkyl) -groups eg, (difluoromethylthio) methyl, (trifluoromethylthio) methyl, (2,2-difluoroethylthio) methyl, (2,2,2-trifluoroethylthio) ) Methyl, 2- (difluoromethylthio) ethyl, 2- (trifluoromethylthio) ethyl, 2- (2,2-difluoroethylthio) ethyl, 2- (2,2,2-trifluoroethylthio) ethyl, 3 -Listing groups such as (difluoromethylthio) propyl, 3- (trifluoromethylthio) propyl, 3- (2,2-difluoroethylthio) propyl or 3- (2,2,2-trifluoroethylthio) propyl. Can be done.
  • C 1 to C 6 haloalkyl sulfinyl C 1 to C 6 alkyl groups means the above-mentioned meanings of the haloalkyl sulfinyl moiety and the alkyl moiety unless otherwise specified (C 1 to C 6 haloalkyl sulfinyl)-.
  • (C 1 to C 6 alkyl) -groups such as (difluoromethylsulfinyl) methyl, (trifluoromethylsulfinyl) methyl, (2,2-difluoroethylsulfinyl) methyl, (2,2,2-trifluoro) Ethylsulfinyl) Methyl, 2- (difluoromethylsulfinyl) ethyl, 2- (trifluoromethylsulfinyl) ethyl, 2- (2,2-difluoroethylsulfinyl) ethyl, 2- (2,2,2-trifluoroethylsulfinyl) ) Ethyl, 3- (difluoromethylsulfinyl) propyl, 3- (trifluoromethylsulfinyl) propyl, 3- (2,2-difluoroethylsulfinyl) propyl or 3- (2,
  • C 1 to C 6 haloalkyl sulfonyl C 1 to C 6 alkyl groups means the haloalkyl sulfonyl moiety and the alkyl moiety as described above (C 1 to C 6 haloalkyl sulfonyl)-unless otherwise specified.
  • (C 1 to C 6 alkyl) -groups eg, (difluoromethylsulfonyl) methyl, (trifluoromethylsulfonyl) methyl, (2,2-difluoroethylsulfonyl) methyl, (2,2,2-trifluoro) Ethylsulfonyl) methyl, 2- (difluoromethylsulfonyl) ethyl, 2- (trifluoromethylsulfonyl) ethyl, 2- (2,2-difluoroethylsulfonyl) ethyl, 2- (2,2,2-trifluoroethylsulfonyl) ) Ethyl, 3- (difluoromethylsulfonyl) propyl, 3- (trifluoromethylsulfonyl) propyl, 3- (2,2-difluoroethylsulfonyl) propyl or 3- (2,
  • the "cyano C 1 to C 6 alkyl group” means a (cyano)-(C 1 to C 6 alkyl) group in which the alkyl moiety has the above meaning, unless otherwise specified, and for example, cyanomethyl.
  • Groups such as 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyanopropane-2-yl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl are mentioned. Can be done.
  • the "tri (C 1 to C 6 alkyl) silyloxy group” means a (C 1 to C 6 alkyl) 3 -Si—O— group in which the alkyl moiety has the above meaning unless otherwise specified.
  • the three alkyl groups may be the same or different from each other, and examples thereof include groups such as trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy or tert-butyldimethylsilyloxy.
  • C 3 to C 6 halocycloalkyl C 1 to C 6 alkyl groups means the above-mentioned meanings of the halocycloalkyl moiety and the alkyl moiety (C 3 to C 6 halocyclo) unless otherwise specified.
  • Alkyl)-(C 1 to C 6 alkyl) -groups eg 2,2-difluorocyclopropylmethyl, 2,2-dichlorocyclopropylmethyl, 2- (2,2-difluorocyclopropyl) ethyl, 2 -(2,2-Dichlorocyclopropyl) ethyl, 2,2-difluorocyclobutylmethyl, 4,4-difluorocyclohexylmethyl and the like can be mentioned.
  • the "phenyl C 1 to C 6 alkyl group” refers to a phenyl- (C 1 to C 6 alkyl) -group in which the alkyl moiety has the above meaning, unless otherwise specified, for example, benzyl, 2 Groups such as -methylbenzyl, 2,3-dimethylbenzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl or 6-phenylhexyl can be mentioned.
  • the "carbon ring” means a non-aromatic 3- to 6-membered monocyclic atom in which all the atoms constituting the ring are 1 to 6 carbon atoms.
  • Specific examples of the carbocycle include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclopropene, cyclobutene, cyclopentene, cyclohexene and the like.
  • heterocycle examples include pyrrolidine, tetrahydrofuran, piperidine, tetrahydropyran, tetrahydrothiophene, tetrahydrothiopyran 1-oxide, tetrahydrothiopyran 1,1-dioxide, thiane, piperazine, morpholine, thiomorpholin, dioxane, dioxolan, Includes, but is not limited to, dithianes and the like.
  • R 8 may be mono-substituted or poly-substituted by R 8
  • R 8s may be substituted by one or more R 8s ".
  • the two or more R8s may be the same or different, respectively, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group , a C3 to C.
  • C 1 to C 6 alkylaminocarbonyl groups (the amino groups may be substituted with R 12 ), C 1 to C 6 haloalkyl aminocarbonyl groups (the amino groups may be substituted with R 12 ), Pyrrolidine-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R 9 ), piperidin-1-ylcarbonyl group (the group may be mono-substituted or poly-substituted with R 9 ), Hydroxy group, C 1 to C 6 alkoxy group, C 3 to C 6 alkenyloxy group, C 3 to C 6 alkynyl oxy group, C 1 to C 6 haloalkoxy group, C 3 to C 6 cycloalkoxy group, C 3 to C 6 halocycloalkyl group, C 3 to C 6 cycloalkyl C 1 to C 6 alkoxy group, C 3 to C 6 halocycloalkyl C 1 to C 6 alkoxy group,
  • phenylsulfinyl group (the group may be mono-substituted or poly-substituted with R 9 )
  • phenylsulfonyl group (the group may be mono-substituted or poly-substituted with R 9).
  • amino groups C 1 to C 6 alkylamino groups (the amino groups may be substituted with R 12 ), C 1 to C 6 haloalkyl amino groups (the amino groups may be substituted with R 12 ).
  • C 1 to C 6 alkylcarbonylamino groups (the amino groups may be substituted with R12 ), C1 to C6 haloalkylcarbonylamino groups (the amino groups may be substituted with R12 ).
  • C 3 to C 6 cycloalkylcarbonylamino groups (the amino groups may be substituted with R12 )
  • phenylcarbonylamino groups (the phenyl groups may be mono- or poly-substituted with R9, the aminos ).
  • the group may be substituted with R 12 ), a C 1 to C 6 alkoxycarbonylamino group (the amino group may be substituted with R 12 ), a C 1 to C 6 haloalkoxycarbonylamino group (the amino group). May be substituted with R 12 ), C 1 to C 6 alkylaminocarbonylamino groups (the amino groups may be substituted with R 12 ), C 1 to C 6 haloalkylaminocarbonylamino groups (the amino groups). May be substituted with R 12 ), C 1 to C 6 alkylsulfonylamino groups (the amino groups may be substituted with R 12 ), C 1 to C 6 haloalkylsulfonyl amino groups (the amino groups are R).
  • C 12 may be substituted), C 3 to C 6 cycloalkylsulfonylamino groups (the amino groups may be substituted by R12 ), phenylsulfonylamino groups (the phenyl groups may be mono-substituted or poly by R9). It may be substituted, and the amino group may be substituted with R12 . ), Tri (C 1 to C 6 alkyl) silyl group, phenyl group (the group may be mono-substituted or poly-substituted with R 9 ), 1,3-benzodioxolyl group (the group may be R 9 ).
  • heteroaryl group the group may be mono- or poly-substituted by R 9
  • heteroaryloxy group the group may be mono- or poly-substituted by R 9 ).
  • a heterocycloalkyl group the group may be mono-substituted or poly-substituted with R9
  • cyano group a nitro group or a thiocyanato group.
  • R 9 may be mono-substituted or poly-substituted by R 9
  • R 9s may be substituted by one or more R 9s ".
  • the two or more R 9s may be the same or different, respectively, a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 haloalkyl group, a C 3 to C.
  • the agriculturally acceptable salt is the compound of the present invention represented by the general formula [I] when a hydroxyl group, a carboxyl group, an amino group or the like is present in the structure or a nitrogen atom of the pyridine ring.
  • the mineral acid include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, sulfuric acid and the like
  • examples of the organic acid include triethylamine and diisopropylamine.
  • Formic acid acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartrate acid, methanesulfonic acid, 4-toluenesulfonic acid or trifluoromethanesulfonic acid. Can be done.
  • Tables 1 to 37 show typical compound examples of the compounds included in the condensed heterocyclic derivative of the present invention represented by the general formula [I].
  • the compounds included in the derivatives of the present invention are not limited thereto.
  • the compound numbers in the table are referred to in the following description.
  • the compounds included in the fused heterocyclic derivative of the present invention may contain E-forms and Z-form geometric isomers depending on the type of substituent, but the present invention describes these E-forms. Includes Z-forms or mixtures containing E-forms and Z-forms in any proportion. Further, the compound included in the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention has all optical activities. Includes body, racemic or diastereomers.
  • the compound of the present invention represented by the general formula [I] can be produced according to the production methods shown below, but is not limited to these methods.
  • “compound represented by the general formula [I]” “compound represented by the formula [I]” and “compound [I]” have the same meaning.
  • the compound represented by the general formula [I-1] can be produced by using the compound represented by the general formula [II-1] according to the method represented by the reaction formula illustrated below. ..
  • K indicates K-1, K-2, K-3, K-4, K-5, K-6, K-7 or K-8.
  • L 1 indicates a halogen atom or a methanesulfonyloxy group
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , m, Y, Z and A have the same meanings as described above.
  • the compound represented by the general formula [I-1] is a compound represented by the general formula [II-1] and the compound [IV-1] in the presence of a suitable catalyst in the presence of a suitable base. It can be produced by reacting under or in the absence of a suitable solvent.
  • the amount of the compound [IV-1] used in this reaction may be appropriately selected from the range of 1 to 100 mol per 1 mol of the compound [II-1], preferably 1.0 to 3.3 mol. Is.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene and the like.
  • Examples of the catalyst that can be used in this reaction include copper (I) chloride, copper (I) bromide, copper (I) iodide, and copper.
  • the amount of the catalyst used may be appropriately selected from the range of 0.01 to 5 mol, preferably 0.01 to 1.2 mol, with respect to 1 mol of the compound [II-1].
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.3 to 25 liters, per 1 mol of the compound [II-1].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [I-1]. be able to.
  • isolated compound [I-1] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [II-3] can be produced by using the compound represented by the general formula [II-2] according to the method consisting of the reaction formulas exemplified below.
  • R 14 indicates a methyl group, an etanoyl group, a methoxymethyl group, a benzyl group or a 4-methoxybenzyl group, and R 1 , R 4 , m and K have the same meanings as described above.
  • the compound represented by the general formula [II-3] is derived from the compound [II-2] from GREEN'S PROTECIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts). It can be manufactured according to the method described in 1.
  • Compound [II-3] can be further purified by column chromatography, recrystallization, distillation or the like, if necessary.
  • the compound represented by the general formula [I-3] can be produced by using the compound represented by the general formula [I-2] according to the method represented by the reaction formula illustrated below. ..
  • R 1a is a C 1 to C 6 alkyl group (the group may be mono-substituted or poly-substituted by R 8 ), a C 2 -C 6 alkenyl group (the group is mono-substituted or poly-substituted by R 8 ). Substituted) , C2 - C6 alkynyl group (the group may be mono-substituted or poly - substituted with R8), C3 - C6 cycloalkyl group (the group may be mono-substituted or poly-substituted with R8).
  • R 15 is a methyl group, an ethanoyl group, a methoxymethyl group, a benzyl group, a 4-methoxybenzyl group or
  • L 2 indicates a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group or a p - toluenesulfonyloxy group
  • R4 , R7 , R8, R 14 , m, Z, A and K have the same meanings as described above.
  • the compound [I-2] and the compound [IV-2] are mixed in a suitable solvent, in the presence of a suitable base, and in the presence of a suitable catalyst. Alternatively, it can be produced by reacting in the absence.
  • the amount of the compound [IV-2] used in this reaction may be appropriately selected from the range of 1.0 to 15.0 mol per 1 mol of the compound [I-2], and is preferably 1.0 to 1 mol. It is 6.0 mol.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • Examples of the catalyst that can be used in this reaction include tetra-n-butylammonium bromide and tetra-n-butylammonium iodide.
  • the amount of the catalyst used may be appropriately selected from the range of 0.01 to 1.0 mol with respect to 1 mol of the compound [I-2], and is preferably 0.05 to 0.5 mol.
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 50 liters, per 1 mol of the compound [I-2].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 30 hours.
  • the compound [I-3] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it.
  • the isolated compound [I-3] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compounds represented by the general formulas [I-5] and [I-6] are the methods comprising the reaction formulas exemplified below using the compounds represented by the general formula [I-4]. Can be manufactured according to.
  • X is a halogen atom
  • a 2 is CR 2 or N
  • R 3a is a C 1 to C 6 alkoxy group, C 3 to C 6 alkenyloxy group, C 3 to C 6 alkynyl oxy group, C 1 to C 6 haloalkoxy groups, C 3 to C 6 cycloalkoxy groups, C 3 to C 6 halocycloalkoxy groups, C 3 to C 6 cycloalkyls C 1 to C 6 alkoxy groups, C 3 to C 6 haloalkoxy groups Alkoxy C 1 to C 6 alkoxy groups, phenyl C 1 to C 6 alkoxy groups (the phenyl group may be mono-substituted or poly-substituted by R 9 ), heteroaryloxy groups (the groups may be mono-substituted or poly-substituted by R 9 ).
  • C 1 to C 6 alkylthio groups C 1 to C 6 alkyl sulfonyl groups, C 1 to C 6 haloalkylthio groups or C 1 to C 6 haloalkyl sulfonyl groups
  • R 3b is C 1 ⁇ C 6 alkyl group, C 2 ⁇ C 6 alkoxy group, C 2 ⁇ C 6 alkoxyyl group , C 1 ⁇ C 6 haloalkyl group, C 3 ⁇ C 6 cycloalkyl group, C 3 ⁇ C 6 halocycloalkyl group, C 3 to C 6 cycloalkyl C 1 to C 6 alkyl groups, C 3 to C 6 halocycloalkyl C 1 to C 6 alkyl groups, phenyl C 1 to C 6 alkyl groups (the groups are mono-substituted or poly-substituted by R9).
  • Step 4-1 That is, the compound represented by the general formula [I-5] is produced by reacting compound [I-4] with a cyanide compound in a suitable solvent in the presence or absence of a suitable catalyst. be able to.
  • Examples of the cyanide compound used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, or a mixture thereof.
  • the amount of the cyanide compound to be used may be appropriately selected from the range of 1 to 100 mol, preferably 1.0 to 5.0 mol, with respect to 1 mol of the compound [I-4].
  • Examples of the catalyst used in this reaction include tetrakis (triphenylphosphine) palladium, [1,1-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct, and the like.
  • the amount of the catalyst used may be appropriately selected from the range of 0.001 to 0.5 mol, preferably 0.01 to 0.2 mol, with respect to 1 mol of the compound [I-4]. be.
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 500 liters, preferably 0.3 to 50 liters, per 1 mol of the compound [I-4].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.
  • the compound After completion of the reaction, the compound is synthesized by filtering out the unnecessary substance from the reaction mixture and concentrating it as it is, or by pouring it into water and filtering out the precipitated solid or extracting it with an organic solvent and then concentrating it.
  • [I-5] can be isolated.
  • the isolated compound [I-5] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • Step 4-2 That is, the compound represented by the general formula [I-6] is suitable for compound [I-4] and compound [IV-3] in a suitable solvent in the presence or absence of a suitable base. It can be produced by reacting in the presence of a catalyst.
  • the amount of the compound [IV-3] used in this reaction may be appropriately selected from the range of 1.0 to 15.0 mol with respect to 1 mol of the compound [I-4], preferably 1.0 to 1.0. It is 6.0 mol.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • the catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand.
  • a transition metal complex tetrakis (triphenylphosphine) palladium (0), [1,1 -Bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct, bis (triphenylphosphine) palladium (II) dichloride, bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium ( Palladium catalyst such as 0), copper salt such as copper (I) iodide, trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2- Bisdiphenylphosphinoetan, 1,3
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 500 liters, preferably 0.3 to 50 liters, per 1 mol of the compound [I-4].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.
  • the compound represented by the general formula [I-4] can be produced by using the compound represented by the general formula [I-7] according to the method consisting of the reaction formulas exemplified below. ..
  • the compound represented by the general formula [I-4] is produced by reacting the compound [I-7] with a halogenating agent in a suitable solvent in the presence or absence of a suitable base. can do.
  • the halogenating agents that can be used in this reaction include chlorine, sulfryl chloride, N-chlorosuccinate imide, sodium hypochlorite, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, and iodine. , N-iodosuccinic acidimide, 1,3-diiodo-5,5-dimethylhydantin, potassium iodate, or a mixture thereof.
  • the amount of the halogenating agent used may be appropriately selected from the range of 0.01 to 10 mol, preferably 0.02 to 2.0 mol, with respect to 1 mol of the compound [I-7].
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglime; dichloromethane, chloroform, 1,2-.
  • Hydrocarbons such as dichloroethane; non-N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, sulfolane, 1,3-dimethyl-2-imidazolidinone and the like
  • Protonic polar solvents such as acetonitrile and propionitrile
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane
  • carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid
  • hydrochloric acid and hydrobromic acid Inorganic acids such as sulfuric acid, nitric acid, and phosphoric acid
  • water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [I-7].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 70 ° C. to the reflux temperature in the reaction system, preferably in the range of ⁇ 20 ° C. to 100 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • reaction mixture is poured into water or the reaction mixture is concentrated as it is, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated.
  • -4] can be isolated.
  • the isolated compound [I-4] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [II-4] can be produced by using the compound represented by the general formula [III-1] according to the method consisting of the reaction formulas exemplified below.
  • R 3c is a hydrogen atom, C 1 to C 6 alkyl group, C 2 to C 6 alkenyl group, C 2 to C 6 alkynyl group, C 1 to C 6 haloalkyl group, C 3 to C 6 cycloalkyl group.
  • C 3 to C 6 halocycloalkyl groups, C 1 to C 6 alkoxy C 1 to C 6 alkyl groups, C 1 to C 6 haloalkyl C 1 to C 6 alkyl groups, R 4 , R 14 , m, X and Z have the same meanings as described above.
  • the compound represented by the general formula [II-2] is produced by reacting compound [III-1] with hydrazine in a suitable solvent in the presence or absence of a suitable base. Can be done.
  • Examples of the hydrazine that can be used in this reaction include anhydrous hydrazine, hydrazine hydrate, and hydrazine hydrochloride.
  • the amount of hydrazine used may be appropriately selected from the range of 1 to 30 mol with respect to 1 mol of the compound [III-1], and is preferably 1 to 20 mol.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, monoglime; N, N-dimethylformamide, N.
  • ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, monoglime; N, N-dimethylformamide, N.
  • the amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [III-1].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [II-4]. be able to.
  • isolated compound [II-4] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-1] can be produced by using the compound represented by the general formula [III-2] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-1] is produced by reacting compound [III-2] and compound [IV-4] in a suitable solvent in the presence of a suitable base. be able to.
  • the amount of the compound [IV-4] used in this reaction may be appropriately selected from the range of 1 to 15 mol with respect to 1 mol of the compound [III-2], preferably 1.0 to 3.0 mol. Is.
  • Examples of the base that can be used in this reaction include lithium diisopropylamide, lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, and potassium bis (trimethylsilyl) amide.
  • the amount of the base used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-2], and is preferably 1.0 to 1.5 mol.
  • Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [III-2].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 100 ° C. to the reflux temperature in the reaction system, preferably in the range of ⁇ 100 ° C. to 40 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-1]. be able to.
  • the isolated compound [III-1] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [II-5] can be produced by using the compound represented by the general formula [III-3] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [II-5] can be produced by reacting the compound [III-3] with a nitrite or a nitrite in an appropriate solvent.
  • nitrite or nitrite ester examples include sodium nitrite, t-butyl nitrite, and isoamyl nitrite.
  • the amount of nitrite or nitrite used may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound [III-3], and is preferably 1.0 to 2.5 mol.
  • Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, 1,4-dioxane, monoglime; dichloromethane, chloroform, 1,2-.
  • ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, 1,4-dioxane, monoglime; dichloromethane, chloroform, 1,2-.
  • Halogenized hydrocarbons such as dichloroethane; nitriles such as acetonitrile and propionitrile; carboxylic acids such as acetic acid, propionic acid and trifluoroacetic acid; inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitrate and phosphoric acid; Water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 300 liters, preferably 0.3 to 20 liters, per 1 mol of the compound [III-3].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 20 ° C. to the reflux temperature in the reaction system, preferably in the range of ⁇ 10 ° C. to 40 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [II-5]. be able to.
  • isolated compound [II-5] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-3] can be produced, for example, by using the compound represented by the general formula [III-4] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-3] is represented by the general formula [III-4] according to the "general reduction section" of the 4th edition (Maruzen) of the Experimental Chemistry Course, Volume 26. It can be produced by reducing the nitro compound.
  • Compound [III-3] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.
  • the compound represented by the general formula [III-4] can be produced, for example, by using the compound represented by the general formula [III-5] according to the method consisting of the reaction formulas exemplified below.
  • the compound [III-5] and the compound [IV-2] are mixed in a suitable solvent, in the presence of a suitable base, and in the presence of a suitable catalyst. Alternatively, it can be produced by reacting in the absence.
  • reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-4]. can do.
  • the isolated compound [III-4] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [II-6] can be produced, for example, by using the compound represented by the general formula [III-3] according to the method consisting of the reaction formulas exemplified below.
  • R 2 , R 16 represents a C 1 to C 6 alkyl group, and R 1a , R 2 , R 4 , R 14 , m and Z represent. It has the same meaning as above.
  • the compound [III-3] and the compound [IV-5] or the compound [IV-6] are mixed in a suitable solvent in the presence of a suitable acid.
  • it can be produced by reacting in the absence or in the presence or absence of a suitable base.
  • the amount of the compound [IV-5] or the compound [IV-6] used in this reaction may be appropriately selected from the range of 1 mol to the equivalent amount of the solvent amount per 1 mol of the compound [III-3]. It is preferably 1.0 to 10.0 mol. However, the compound [IV-6] can also be used as the above-mentioned solvent.
  • Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; methanesulfonic acid and trifluoromethanesulfonic acid. Sulfonic acids and the like can be mentioned.
  • the amount of the acid to be used may be appropriately selected from the range of 0.1 to 1 mol corresponding to the amount of the solvent with respect to 1 mol of the compound [III-3], and is preferably 0.1 to 100.0 mol.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetracarbonate, 1,4-dioxane, monoglime; benzene, toluene, xylene, mesityrene, etc.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and rutidin; third such as triethylamine and tributylamine. Secondary amines; orthoesters such as trimethyl orthoacetate, triethyl orthoacetate, trimethyl orthoacetate, triethyl orthoacetate and the like, or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [III-3].
  • the reaction temperature of this reaction may be usually selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of ⁇ 10 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • the compound [II-6] is isolated by concentrating the reaction mixture as it is, or by pouring the reaction mixture into water or the like, extracting with an organic solvent, and then concentrating the reaction mixture. can do.
  • the isolated compound [II-6] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [II-7] can be produced, for example, by using the compound represented by the general formula [III-6] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [II-7] can be produced by reacting the compound [III-6] with carbon disulfide in a suitable solvent in the presence of a suitable base. ..
  • the amount of carbon disulfide used in this reaction may be appropriately selected from the range of 1 to 35 mol per 1 mol of the compound [III-6], and is preferably 1 to 25 mol.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [III-6].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • the compound [II-7] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it.
  • the isolated compound [II-7] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-6] can be produced, for example, by using the compound represented by the general formula [III-7] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-6] can be produced by reacting the compound [III-7] in a suitable solvent in the presence of a suitable acid.
  • Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, and phosphoric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; methanesulfonic acid and trifluoromethanesulfonic acid. Sulfonic acids and the like can be mentioned.
  • the amount of the acid used may be appropriately selected from the range of 0.1 to 1 mol corresponding to the amount of the solvent with respect to 1 mol of the compound [III-7], and is preferably 0.1 to 100 mol.
  • Solvents that can be used in this reaction include, for example, ethers such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, monoglyme; benzene, toluene, xylene, mesityrene, etc.
  • Aromatic hydrocarbons such as chlorobenzene; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol and methyl cellosolve; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 25 liters, per 1 mol of the compound [III-6].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • the compound [III-6] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it.
  • the isolated compound [III-6] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-7] can be produced, for example, by using the compound represented by the general formula [III-8] according to the method consisting of the reaction formulas exemplified below.
  • R 1a , R 4 , R 17 , R 18 , m, L 2 and Z have the same meanings as described above.
  • the compound [III-8] and the compound [IV-2] are mixed in a suitable solvent, in the presence of a suitable base, and in the presence of a suitable catalyst. Alternatively, it can be produced by reacting in the absence.
  • reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-7]. can do.
  • isolated compound [III-7] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-8] can be produced, for example, by using the compound represented by the general formula [III-9] according to the method consisting of the reaction formulas exemplified below.
  • R 18 C 1 to C 6 alkyl groups, 1,1-dioxide-3-oxobenzothiazole-2-yl, R 4 , R 17 , R 18 , m and Z have the same meanings as described above.
  • the compound represented by the general formula [III-8] is derived from the compound [III-9] from GREEN'S PROTECIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts). It can be manufactured according to the method described in 1.
  • Compound [III-8] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.
  • the compound represented by the general formula [I-8] is produced, for example, by using the compound represented by the general formula [III-10] according to the method consisting of the reaction formulas exemplified below. be able to.
  • L 6 indicates a leaving group such as 1H-imidazole-1-yl, -OCCl 3 , -NH 2 , -O (imidyl N-succinate), R 4 , R 7 , m, Z and A has the same meaning as described above.
  • the compound represented by the general formula [I-8] is produced by reacting compound [III-10] and compound [IV-8] in a suitable solvent in the presence of a suitable base. be able to.
  • the amount of the compound [IV-8] used in this reaction may be appropriately selected from the range of 1 to 15 mol, preferably 1.0 to 5.0 mol, with respect to 1 mol of the compound [III-10]. Is.
  • Examples of the bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide.
  • Alkaline metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate
  • inorganic bases such as alkali metal bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate; lithium hydride, sodium hydride, hydrogenation Metal hydrides such as potassium; metal salts of alcohols such as sodium methoxydo, sodium ethoxydo, potassium tert-butoxide; or triethylamine, tributylamine, diisopropylethylamine, N, N-dimethylaniline, pyridine, 2,6-lutidine , 4-N, N-dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and other organic bases and the like can be
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide , Sulfolane, aprotonic polar solvents such as 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propionitrile and the like.
  • Nitriles such as ethyl acetate, butyl acetate, ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and heptane; pyridines such as pyridine, picolin and lutidine; third such as triethylamine and tributylamine Secondary amines; water or a mixed solvent thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 80 liters, per 1 mol of the compound [III-10].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 150 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • the compound [I-8] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it.
  • the isolated compound [I-8] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-11] can be produced, for example, by using the compound represented by the general formula [III-12] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-11] is derived from the compound [III-12] from GREEN'S PROTECIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts). It can be manufactured according to the method described in 1.
  • the compound [III-11] can be further purified by column chromatography, recrystallization, distillation or the like, if necessary.
  • the compound represented by the general formula [III-12] can be produced, for example, by using the compound represented by the general formula [III-13] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-12] is represented by the general formula [III-13] according to the "general reduction section" of the 4th edition (Maruzen) of the Experimental Chemistry Course, Volume 26. It can be produced by reducing the nitro compound.
  • Compound [III-12] can be further purified by column chromatography, recrystallization, distillation, etc., if necessary.
  • the compound represented by the general formula [III-13] can be produced, for example, by using the compound represented by the general formula [III-14] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-13] is a compound represented by the general formula [III-14] and the compound [IV-1] in the presence of a suitable catalyst in the presence of a suitable base. It can be produced by reacting under or in the absence of a suitable solvent.
  • reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-13]. can do.
  • the isolated compound [III-13] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [III-14] can be produced, for example, by using the compound represented by the general formula [III-15] according to the method consisting of the reaction formulas exemplified below.
  • the compound represented by the general formula [III-14] can be produced by reacting the compound [III-15] with sodium sulfide or sodium hydrogen sulfide in an appropriate solvent.
  • the amount of sodium sulfide or sodium hydrogen sulfide used in this reaction may be appropriately selected from the range of 1 to 15 mol with respect to 1 mol of the compound [III-15], preferably 1.0 to 3.0 mol. Is.
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methyltetrachloride, 1,4-dioxane, and monoglyme; N, N-dimethylformamide, N.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [III-15].
  • the reaction temperature of this reaction may be selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of 0 ° C. to 100 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.
  • the compound [III-14] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it.
  • the isolated compound [III-14] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the compound represented by the general formula [I-10] is produced, for example, by using the compound represented by the general formula [I-9] according to the method consisting of the reaction formulas exemplified below. be able to.
  • the compound represented by the general formula [I-10] can be produced by reacting the compound [I-9] with a nucleophilic fluorinating agent in an appropriate solvent.
  • nucleophilic fluorinating agent examples include (diethylamino) sulfatrifluoride and bis (2-methoxyethyl) aminosulfatrifluoride.
  • the amount of the nucleophilic fluorinating agent to be used may be appropriately selected from the range of 2 to 10 mol with respect to 1 mol of the compound [I-9], and is preferably 2.0 to 5.0 mol.
  • solvents such as diethyl ether, methyl tert-butyl ether, cyclopentylmethyl ether, tetrahydrofuran, 2-methylhydrocarbon, 1,4-dioxane, and monoglyme; benzene, toluene, xylene, and mesityrene.
  • Aromatic hydrocarbons such as chlorobenzene; Halogenized hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; Alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, methyl cellosolve; acetonitrile, propio Nitriles such as nitriles; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane, or mixed solvents thereof and the like can be mentioned.
  • the amount of the solvent used is 0.1 to 100 liters, preferably 0.1 to 15 liters, per 1 mol of the compound [I-9].
  • the reaction temperature of this reaction may be usually selected from an arbitrary temperature range from ⁇ 30 ° C. to the reflux temperature in the reaction system, preferably in the range of ⁇ 10 ° C. to 60 ° C.
  • reaction time of this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.
  • the compound [I-10] can be isolated by pouring the reaction mixture into water or the like, extracting it with an organic solvent, and then concentrating it.
  • the isolated compound [I-10] can be further purified by column chromatography, recrystallization and the like, if necessary.
  • the herbicide of the present invention contains a fused heterocyclic derivative represented by the general formula [I] of the present invention or an agriculturally acceptable salt thereof as an active ingredient.
  • the herbicides of the present invention have excellent herbicidal efficacy, and some show excellent selectivity between useful plants and weeds, and are useful as pesticide compositions in agricultural land, especially as herbicides. That is, the compound of the present invention can be used for foliage treatment, soil treatment, seed powder coating treatment, soil mixing treatment, pre-sowing soil treatment, simultaneous sowing treatment, post-sowing soil treatment, and sowing in fields where useful plants are cultivated or non-agricultural land. It has a herbicidal effect on various weeds in the simultaneous soil covering and mixing treatment.
  • the herbicide of the present invention can contain an additive component (carrier) usually used in a pesticide preparation, if necessary.
  • the additive component examples include carriers such as solid carriers or liquid carriers, surfactants, binders and tackifiers, thickeners, colorants, spreading agents, spreading agents, antifreeze agents, anti-caking agents, and the like.
  • carriers such as solid carriers or liquid carriers, surfactants, binders and tackifiers, thickeners, colorants, spreading agents, spreading agents, antifreeze agents, anti-caking agents, and the like.
  • examples thereof include a disintegrant, a decomposition inhibitor, and the like, and if necessary, a preservative, a plant piece, or the like may be used as an additive component. Further, these additive components may be used alone or in combination of two or more.
  • solid carrier examples include pyrophyllite clay, kaolin clay, silica stone clay, talc, diatomaceous earth, zeolite, bentonite, acidic white clay, active white clay, attapargas clay, vermiculite, pearlite, peasite, and white carbon (synthetic silicic acid,).
  • Mineral carriers such as synthetic silicate), titanium dioxide; vegetable carriers such as wood flour, corn stalks, walnut shells, fruit nuclei, fir, fir, oak, bran, soybean flour, powdered cellulose, starch, dextrin, sugars, etc.; Inorganic salt carriers such as calcium carbonate, ammonium sulfate, sodium sulfate, potassium chloride; and polymer carriers such as polyethylene, polypropylene, polyvinyl chloride, polyvinyl acetate, ethylene-vinyl acetate copolymer, and urea-aldehyde resin can be mentioned. can.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol; and many such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, 2-propanol, butanol, and cyclohexanol
  • ethylene glycol diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Hyvalent alcohols Polyhydric alcohol derivatives such as propylene glycol ethers; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, isophorone; ethyl ether, 1,4-dioxane, cellosolve, dipropyl ether, Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosine, mineral oil; fragrances such as toluene, C 9 -C 10 alkylbenzene, xylene, solvent naphtha, alkylnaphthalene, high boiling aromatic hydrocarbons, etc.
  • Group hydrocarbons Halogenized hydrocarbons such as 1,2-dichloroethane, chloroform, carbon tetrachloride; Esters such as ethyl acetate, diisopropylphthalate, dibutylphthalate, dioctylphthalate, dimethyl adipate; lactones such as ⁇ -butyrolactone Classes; amides such as N, N-dimethylformamide, N, N-diethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone; nitriles such as acetonitrile; sulfur compounds such as dimethylsulfoxide; large Vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, coconut oil, and castor oil, lower alkyl esters of fatty acids derived from the vegetable oils; water and the like can be mentioned.
  • Halogenized hydrocarbons such as 1,2-dichloroethane, chloroform, carbon tetrachlor
  • surfactant examples include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, and poly.
  • binder and tackifier examples include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sugar, polyvinylpyrrolidone, arabic rubber, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, polyethylene glycol and polyethylene. Oxides, natural phospholipids (eg, cepharic acid, lecithin, etc.) and the like can be mentioned.
  • Thickeners include, for example, xanthan gum, guar gum, carboxymethyl cellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch derivatives, water-soluble polymers such as polysaccharides; high-purity bentonite, inorganic fine powder such as white carbon. , Organic fine powder such as organic bentnite can be mentioned.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dyes, azo dyes, and metallic phthalocyanine dyes.
  • the spreading agent examples include silicone-based surfactants, cellulose powders, dextrins, processed starches, polyaminocarboxylic acid chelate compounds, crosslinked polyvinylpyrrolidones, maleic acid / styrene copolymers, methacrylic acid copolymers, and polyhydric alcohols.
  • examples thereof include a half ester of the polymer of the above and a dicarboxylic acid anhydride, a water-soluble salt of polystyrene sulfonic acid, polyoxyethylene alkanediols, polyoxyethylene alkyndiols, alkynediols and the like.
  • various surfactants such as sodium dialkyl sulfosuccinate, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester; paraffin, terpene, polyamide resin, polyacrylic acid salt, etc. , Polyoxyethylene, wax, polyvinylalkyl ether, alkylphenol formalin condensate, synthetic resin emulsion and the like.
  • antifreeze agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • anti-caking agent examples include polysaccharides such as starch, alginic acid, mannose, and galactose; polyvinylpyrrolidone, white carbon, ester gum, petroleum resin, and the like.
  • disintegrant examples include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleine anhydride.
  • examples thereof include acid copolymers and starch / polyacrylonitrile graft copolymers.
  • decomposition inhibitor examples include desiccants such as zeolite, quicklime, and magnesium oxide; antioxidants such as phenol-based, amine-based, sulfur-based, and phosphoric acid-based; ultraviolet absorbers such as salicylic acid-based and benzophenone-based. Can be mentioned.
  • desiccants such as zeolite, quicklime, and magnesium oxide
  • antioxidants such as phenol-based, amine-based, sulfur-based, and phosphoric acid-based
  • ultraviolet absorbers such as salicylic acid-based and benzophenone-based. Can be mentioned.
  • preservative examples include potassium sorbate, 1,2-benzthiazoli-3-one and the like.
  • plant pieces examples include sawdust, palms, corn cobs, tobacco stems, and the like.
  • the content ratio thereof is usually 5 to 95%, preferably 20 to 90% for a carrier such as a solid carrier or a liquid carrier on a mass basis.
  • the surfactant is usually selected in the range of 0.1 to 30%, preferably 0.5 to 10%, and the other additives are selected in the range of 0.1 to 30%, preferably 0.5 to 10%.
  • the herbicide of the present invention includes powders, powders and granules, granules, wettable powders, aqueous solvents, granule wettable powders, tablets, jumbo agents, emulsions, oils, oily suspensions, liquids, flowable agents, emulsions, and Microemulsion agent, Suspension emulsion agent, Micro-spray agent, Microcapsule agent, Jumbo agent, Bean crush ⁇ registered trademark> agent, Smoke agent, Aerosol agent, Bait agent, Paste agent, Foam agent, Carbon dioxide gas preparation, Paint, It is used by formulating it into any dosage form such as wood protective paint and sealing agent.
  • these preparations can be used as they are, or they can be diluted to a predetermined concentration with a diluent such as water.
  • a diluent such as water.
  • the application of various formulations or dilutions thereof containing the compounds of the present invention is usually a commonly used application method, that is, spraying (eg, spraying, misting, atomizing, dusting, granulation, water surface application, etc.). Box application, etc.), soil application (eg, contamination, irrigation, etc.), surface application (eg, coating, powder coating, coating, etc.), seed treatment (eg, smear, powder coating treatment, etc.), immersion, poison bait, smoke It can be done by application or the like.
  • the pesticide composition of the present invention can be used by spraying foliage, soil application, water surface application, or the like.
  • the pesticide composition of the present invention particularly a herbicide, is used in soil, especially in upland fields or paddy fields where useful plants are cultivated.
  • the blending ratio of the active ingredient is appropriately selected as needed, but in the case of powder or granules, 0.01 to 10% (weight), preferably 0.05 to 5 It is better to select from the range of% (weight) as appropriate.
  • weight preferably 0.01 to 10% (weight), preferably 0.05 to 5
  • weight it is preferable to appropriately select from the range of 1 to 50% (weight), preferably 5 to 30% (weight).
  • flowable agent or an oil suspension agent it is preferable to appropriately select from the range of 1 to 40% (weight), preferably 5 to 30% (weight).
  • the application rate of the pesticide composition of the present invention varies depending on the type of compound used, target weeds, development tendency, environmental conditions, dosage form used, and the like.
  • the active ingredient may be appropriately selected from the range of 1 g to 50 kg, preferably 10 g to 10 kg per hectare. ..
  • the pesticide composition of the present invention also contains at least one other pesticide active ingredient, for example, another disease control agent component, an insecticide component, an acaricide component, and the like.
  • at least one other pesticide active ingredient for example, another disease control agent component, an insecticide component, an acaricide component, and the like.
  • insecticide components for example, another disease control agent component, an insecticide component, an acaricide component, and the like.
  • repellent components herbicides components, pesticide components, microbial pesticide components, plant growth regulator components, fertilizers, soil improvers, etc. It may be used together.
  • each single ingredient can be mixed and used at the time of application. Further, each of the individual individual components may be used sequentially, or may be applied after a few days. When the application is performed after a certain number of days, the treatment may be performed at intervals of about 1 to 40 days, although it depends on other components used.
  • the pesticide composition of the present invention at least one compound selected from the fused heterocyclic derivative represented by the general formula [I] and an agriculturally acceptable salt, and at least one selected from other pesticide active ingredients.
  • it is usually applied at a mass ratio of 100: 1 to 1: 100, preferably 20: 1 to 1:20, particularly 10: 1 to 1:10.
  • the compounding ratio (mass%) of the active ingredient in the pesticide composition of the present invention is appropriately selected as necessary.
  • a powder, a powder or granule, a fine granule, etc. it is preferable to appropriately select from the range of 0.01 to 20%, preferably 0.05 to 10%, and in the case of a granule, etc., 0.1 to It is preferable to appropriately select from the range of 30%, preferably 0.5 to 20%, and in the case of a wettable powder, granule wettable powder, etc., appropriately select from the range of 1 to 70%, preferably 5 to 50%.
  • formulations are diluted to an appropriate concentration and sprayed, or applied directly.
  • the pesticide composition of the present invention is generally applied at an active ingredient concentration of 0.1 to 5000 ppm when diluted with a diluent.
  • the application rate per unit area is 0.1 to 5000 g per ha as the active ingredient compound, but is not limited thereto.
  • the pesticide composition of the present invention is sufficiently effective even when the compound of the present invention is used alone as an active ingredient, but other pesticides such as insecticides and acaricides are available as needed.
  • insecticides and acaricides are available as needed.
  • Herbicide compound or herbicidal active ingredient Ioxynil (including salts with lithium salt, sodium salt, octanonic acid, etc.), acronifen, achlorein, azafenidin, asifluorfen (including salts with sodium, etc.) ), Azimsulfuron, ashlum, acetochlor, atrazine, anilophos, amicarbasone, amidosulfuron, amidosulfuron, amidosulfuron.
  • Chlor (aminocyclopyrachlor), aminopyrlide, amiprophos-methyl, amethrin, atrazine mosaic virus (Araujia Mosaic Viras), arachlor (Including salts with sodium and the like), ancymidol, isouron, isoxachlortole, isoxaflutole, isoxaben, isodecyl alcohol ethoxylate (isodecylcoltole) ), Isoproturnon, ipfencarbazone, imazaquin, imazapic (including salts with amines, etc.), imazapyr (containing salts such as imazapyr) (isopropylamine and the like).
  • imazamethabenz ⁇ (imazamethabenz-methyl) ⁇ (imazamox) ⁇ (imazethapyr) ⁇ (imazosulfuron) ⁇ (indaziflam) ⁇ (indanofan) ⁇ (eglinazine-ethyl) ⁇ (esprocarb) ,workman Tamethosulfuron-methyl, ethalfururalin, ethidimuron, ethoxysulfuron, ethoxyphen, ethoxyphen, ethoxyphenethyl , Etobenzanid, epilifenasyl, endotal disodium, oxadiazon, oxadiargyl, oxadialgyl, oxadiargyl, oxadichlorofen Oryzalin, Obuda Pepper Virus, orthosulfamuron, orbencarb, oleic acid, oleic acid, caprylic acid, caprylic acid, caprylic acid, cap
  • Methylamine dimethylamine or trimesium and other salts
  • glufosinate including amine or sodium and other salts
  • glufosinate-P glufosinate-P.sodium salt (glufosinate-) P-sodium, colletotric, clodinahop, clodinahop-propargyl, clopyrlide (including monoethanolamine salt), chromophen (Clomeprop), colletotrichum-methyl, chloramben, chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron-thyl, chlorsulfuron.
  • ketospiradox including salts such as sodium, calcium or ammonia
  • Colletotrichum orbiculare Colletotrichum gloeospolyeuides (Collettrichum gloeosporioides)
  • Colletotrichum Saflufenacil salmentine, cyanazine, cyanamide, diuron, diethatill-eth yl), dioxopyridrione, dicamba (amines, diethylamines, isopropylamines, diglycolamines, dimethylammoniums, diolamines, isopropylammoniums, auramines, potassium, tralolamines, BAPMA (N, N-bis).
  • Dichlolrop dichlolprop-P (including salts such as dimethylammonium, potassium, sodium, choline, or esters such as butothyl ester, 2-ethylhexyl ester, isoctyl ester, methyl ester), diquat.
  • diquat diquat dibromide, dithiopyr, siduron, dinitramine, cinidon-ethyl, cinosulfone (cinosulfuron), cinosulfuron (cinosulfuron) Includes), dinoterb, cihalohop, cyhalohop-butyl, cypyrafluone, diphenamide, diphenzocoat, diphenzocoat, diphenzoqut.
  • Trifluorixylfuron (including salts such as sodium), trivenuron-methyl, tropyllate, naptalam (including salts with sodium etc.), naproanilide (naproanilide), napropamide, napropamide.
  • pyribenzaxim pyrimisulfan, pyriminobac-methyl, pyroxasulfone, pyroxslum, phytopsola palmiphorn, phytophylon Sulfone, fenoxaprop (including methyl, ethyl, isopropyl ester), phenoxaprop-P (including methyl, ethyl, isopropyl ester), fenquinotrione, Fentiaprop-ethyl, fentrazamide, fenpyrazone, phenmedifam, former kenopodicola, former Helbarum, Forma macrostomah, Butachlor, butafenacil, butamifos, butylate, puccinia canalicula, puccinia canalicula Butenachlor, butralin, butroxydim, frazasulfuron, flamprop (including methyl, ethyl, isopropyl ester), flamprop-M
  • Ethyl including isopropyl ester
  • primisulfuron primisulfuron-methyl, fluazihop-butyl, fluazihop-P, fluazihop-P.butyl fluazifop-P-butyl, fluazolate, fluomethuron, fluoroglycophen-ethyl, flucarbazone-sodium, flucarbazone-sodium, flucuronle-flu of Fluthiaset-methyl, flupyrsulfuron-methyl (including salts such as sodium, calcium or ammonia), flufenacet, flufenpyr-ethyl, full Propanate (including sodium salt), flupoxame, flumioxazine, flumiclorac-pentyl, flumethzulum, flulydone, flulydone, fluridone, flulydone.
  • (Fluroxypyr) Esters such as tomethyl and meptyl, or salts such as sodium, calcium and ammonia), flurochloridone, pretilachlor, procarbazone (including salts with sodium etc.), prodiamine (including salts with sodium etc.) Prodiamine, Prosulfuron, Prosulfocarb, Propazinehop, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine, Propazine
  • Benzophenap bentazone, pentanochlor, pendimethalin, pentoxazone, benfururalin, benfururalin, benefuresamine, benfuresate , Foramsulfuron, forchlorphenuron, mecoprop (sodium, potassium, isopropylamine, triethanolamine, dimethylamine, diolamine, traroamine, salts of choline, etc., or etadir Contains esters such as esters, 2-ethylhexyl esters, isoctyl esters, methyl esters, etc.), mecoprop-P-potassium, mesosulfuron (including esters such as methyl), mesotrione.
  • Metazachlor metazosulfuron, methabenzthiazuron, metamitron, metamihop, sodium metham, sodium salt, etc.
  • DSMA sodium metham, sodium salt, etc.
  • methiozolin methyldymuron, metoxuron, metoslum, metsulfuron-methyl, metulfuron-methyl, metobromeron, metobromeron Methylbuzin, mepicote chloride (m) epiquat chloride, mefenacet, monosulfuron (including methyl, ethyl, isopropyl ester), monolinuron, molinate, iodosulfuron, iodosulfuron-sodium salt.
  • esters such as esters, isoctyl esters, isopropyl esters, meptyl esters, tefryl esters, etc.), 2,4-dichlorophenoxybutyric acid (2,4-DB) (amines, diethylamines, triethanolamines, isopropylamines, etc.)
  • Contains salts such as dimethylammonium, choline, sodium or lithium, or esters such as isoctyl esters), 2-amino-3-chloro-1,4-naphthoquinone (ACN), 2-methyl-4-chlorophenoxyacetic acid (including 2-methyl-4-chlorophenoxyacetic acid).
  • MCPA including salts such as sodium, dimethylammonium and choline, or esters such as 2-ethylhexyl ester, isoctyl ester and ethyl ester
  • 2-methyl-4-chlorophenoxybutyric acid MCPB
  • MCPB 2-methyl-4-chlorophenoxybutyric acid
  • DNOC 4,6-dinitro-O-cresol
  • AE-F-150944 code number
  • IR-6396 code number
  • MCPA-thioethyl MCPA-thioethyl
  • SYS-298 code number
  • SYS-300 code number
  • S-ethyldipropylthiocarbamate EPTC
  • S-metholachlor S-9750 ( Code number)
  • MSMA MSMA
  • HW-02 code number
  • Plant growth regulator 1-naphthylacetamide, 1-methylcyclopropene, 1,3-diphenylurea, 2,3,5-triiodobenzoic acid (2,3,5) -Triiodobenzoic acid), 2-methyl-4-chlorophenyloxybutyric acid (MCPB) [including sodium salts, ethyl esters, etc.], 2- (naphthalene-1-yl) acetic acid (2- (naphthalene-1-yl) aceticide) , 2,6-diisopropylnaphthalene, 3-[(6-chloro-4-phenylquinazoline-2-yl) amino] propan-1-ol (3-[(6-chloro-4-) phenylquinazoline-2-yl) amino] propane-1-ol), 4-oxo-4- (2-phenylethyl) aminobutyric acid (chemical name, CAS registration number: 1083-55-2), 4-chlorophenoxyacetic
  • Isoxadiphen isoxadiphen-ethyl, oxabetrinil, octane-1,8-diamine (octane-1,8-diamine), cloquintocet, cloquintocet-cutcet.
  • insecticidal agents insecticide active ingredients
  • acaricides mite-killing active ingredients
  • nematode-killing agents nematode-killing active ingredients
  • synergistic agent compounds co-active ingredients
  • Bacillus thuringiensis subspecies Islaelensis Bacillus thuringiensis subspecies Islaelensis (Bacillus thuringiensis subsp. Islaelensis), Bacillus thuringiensis subspecies Kurstaki (Bacillus thuringie) nsis subsp. Kurstaki), Bacillus thuringiensis subspecies Tenebrionis (Bacillus thuringiensis subsp.
  • Halphenprox halophenothrin, bioallethrin, bioallethrin S-cyclopentenyl, bioallethrin S-cyclopentenyl, biolesmethrin (biorethrin) DCIP), bistriflulon, hydramethylnon, biphenazete, biphenothrin, pyflubude, pyflubulude, piperonylbutoxide, piperonylbutoxide (piperon) Roll (pyrafluple), pyridaphenthion, pyridaben, pyridalyl, pyrifluququinazon, pyriproll, pyridifluor, pyriproxyphen (pyridiplo) Robin (pyriminostrobin), pyrimiphos-methyl, pyrethrin, famphur, fipronil, fenazaquin, phenaziphos, phenothrin, phenomiphos P
  • fenbutatin oxide calcium cyanide
  • organic tin compounds nicotine-sulfate, (Z) -11-tetradecenyl-acetate, (Z) -11-hexadecenate, (Z) -11-hexadecenate.
  • bactericidal agents bactericidal active ingredients
  • disease control agent compounds that may be mixed or used in combination are exemplified below.
  • Bactericidal active ingredient or disease control agent compound Agrobacteria radiobacter, azaconazole, acibenzolar-S-methyl, azoxystrobin, azoxystrobin, anilazine, anilazine aminopylifen, amethoctadine, aldimorph, isotianil, isopyrazam, isofetamid, isofetamide, isofluciplam, isoflucypla ipflufenoquin, ipfentrifluconazole, iprodione, iplovalicarb, iprobenfos, imazaryl, iminoctadine, iminoctadine, iminoctadine, iminoctadine , Imibenconazole, impylfluxam, imprimatin A, imprimatin B, edifenphos, edifenphos, etaconazol, etaconaz (Ethirimol), e
  • biopesticide that may be mixed or used in combination is illustrated below.
  • Biopesticide ⁇ (Haplothrips brevitubus) ⁇ (Franklinothrips vespiformis) ⁇ (Diglyphus isaea) ⁇ (Encarsia formosa) ⁇ ⁇ (Amblyseius cucumeris) ⁇ (Pseudaphycus malinus) ⁇ (Amblyseius womersleyi) ⁇ (Aphidius colemani) ⁇ (Eretmocerus eremicus) ⁇ (Aphidoletes aphidimyza) ⁇ (Amblyseius swirskii) ⁇ (Orius strigicollis) ⁇ (Phytoseiulus persimilis) ⁇ (Amblyseius degenerans) ⁇ (Phytoseiulus persimilis) ⁇ (Orius sauteri) ⁇ (Dacnusa sibirica) ⁇ (Amblyseius californicus) ⁇ (
  • Agricultural materials Ethylene, hypochlorite water (limited to those obtained by electrolyzing hydrochloric acid or potassium chloride aqueous solution), sodium bicarbonate, vinegar, humus, humic acid, fluboic acid, seaweed extract, polysaccharides, amino acids, microorganisms Materials, functional ingredients derived from animals and plants, microbial metabolites, microbial activators, soil spreading agents, soil permeability control materials, soil water retention materials, etc., and biostimulants.
  • Fertilizers include inorganic fertilizers and organic fertilizers.
  • Agricultural fertilizer component Ammonium chloride, ammonium sulfate, ammonium nitrate, ammonium dihydrogen phosphate, urea ammonium nitrate, urea, lime nitrogen, potassium nitrate, lime perphosphate, triple superphosphate, potassium dihydrogen phosphate, potassium chloride, potassium sulfate, potassium carbonate, Potassium silicate, potassium phosphite, oil cake, fish flour, rice bran, bat guano, fermented chicken manure.
  • the herbicide of the present invention is applied to useful plants, or places where useful plants are to be grown or grown, or to non-agricultural land at the same time or by dividing them into useful plants. It is possible to control the growth of undesired plants or plants that are undesired in terms of land management.
  • the useful plants referred to in the present invention include field crops or paddy crops, horticultural crops (vegetables, fruit trees), ornamental trees (flowering trees, street trees), shiva, flowers, and foliage plants. It includes, but is not limited to, medicinal plants and timbers, including, but not limited to, the following.
  • Field crops or paddy crops Corn, rice, wheat, durum wheat, barley, lime, rye wheat, spelled wheat, club wheat, embaku, sorghum, cotton, soybean, alfalfa, peanut (light bean), pea (green bean), lye, azuki, sage, ryokuto, uradomame , Benibanaingen, ricebean, moth bean, teparly bean, soramame, pea, chick, lens bean, rupin, kimame, buckwheat, tensai, rapeseed, canola, sunflower, sugar cane, cassaba, nagaimo, oil palm, nanyouaburi, hemp Benibana, Chanoki, Wheat, Tobacco, Camerina, Tef, Guayur, Paragom tree, etc.
  • Horticultural crops Vegetables: Vegetables of the family Brassicaceae (egg, tomatoes, peppers, peppers, potatoes, etc.), vegetables of the family Urina (cucumbers, pumpkins, zucchini, watermelons, melons, squash, etc.) , Karasina, broccoli, cauliflower, etc.), Kiku family vegetables (gobo, shungiku, artichoke, lettuce, etc.), lily family vegetables (negi, onion, garlic, asparagus, etc.), seri family vegetables (carrot, parsley, celery, American bowfew) Etc.), Brassicaceae vegetables (Horensou, Beta vulgaris, etc.), Perilla family vegetables (Shiso, Mint, Basil, Lavender, etc.), Strawberries, Sweet potatoes, Yamanoimo, Satoimo, Sesame, etc.
  • Horticultural crops (fruit trees): Nuts (apples, pears, Japanese pears, Chugokunashi, Karin, Marumero, etc.), drupes (peaches, plums, nectarins, seaweeds, apricots, apricots, prunes, etc.), citrus fruits (unshu mikan, oranges, lemons, limes, etc.) Grapefruit, etc.), nuts (kuri, walnut, pear, almond, hazelnut, pistachio, cashew nut, macadamia nut, pecan nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, biwa , Banana, coffee, nut palm, coco palm, apricot palm, etc.
  • Ornamental wood (flowering trees, roadside trees): Ash, Kabanoki, Hanamizuki, Eucalyptus, Ginkgo, Lilac, Maple, Kashi, Poplar, Cercis chinensis, Fu, Platanus, Keyaki, Thuja, Mominoki, Tsuga, Nezu, Matsu, Tohi, Ichii, Nire, Tochinoki, Coral, Inumaki, Sugi Hinoki, Croton, Masaki, Japanese photinia, etc.
  • Shiva Zoysia japonica (Zoysia japonica, Zoysia tenuifolia, etc.), Bermudagrass (Gyogishiba, etc.), Bentgrass (Arostis capillaris, Agrostis capillaris, etc.), Bluegrass (Nagahagusa, Osuzumenokatabira, etc.), Fescues (Tall fescue, Agrostis capillaris, etc.) Fescues, etc.), ryegrass (Dactylis, Perennial ryegrass, etc.), Zoysia japonica, Agrostis capillaris, etc.
  • foliage plants Rose, carnation, kiku, turkey, kasumisou, gerbera, marigold, salvia, petunia, verbena, tulip, aster, lindo, lily, pansy, cyclamen, orchid, tin orchid, lavender, stock, habutton, primula, poinsettia, gradialus, cattleya , Daisy, Verbena, Cyclamen, Begonia, etc.
  • Medicinal plants Chamomiles, licorice, turmeric, ginseng, Coptis chinensis, peony, poppy, etc.
  • Lumber Abies sachalinensis, spruce, pine, hiba, sugi, cypress, eucalyptus, etc.
  • the useful plant referred to in the present invention is a 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitor such as isoxaflutol, an imazetapill, and an acetolactate synthase (ALS) inhibitor such as thifensulfuron-methyl.
  • 4-HPPD 4-hydroxyphenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • 5-enolpyrvirsikimic acid-3-phosphate (EPSP) synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as gluhocinate, acetyl CoA carboxylase (ACCCace) inhibitors such as setoxydim, flumioxadin, epiriphenacyl Protoporphyrinogen oxidase (PPO) inhibitors such as, photochemical II inhibitors such as bromoxinyl, and herbicides such as dicamba and 2,4-D are imparted by classical breeding methods and gene recombination techniques. Also includes plants that have been cultivated.
  • Examples of "useful plants” that have been endowed with resistance by classical breeding methods include rapeseed, wheat, sunflower, rice, and corn that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill. It is already sold under the product name.
  • soybeans that are resistant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl by the classical breeding method, and are already sold under the trade name of STS soybean.
  • sorghum resistant to sulfonylurea-based acetolactic acid synthase (ALS) -inhibiting herbicides by classical breeding methods is already on the market.
  • sugar beets resistant to thiencarbazone-resistant acetolactic synthase (ALS) -inhibiting herbicides by classical breeding methods are already on the market.
  • acetyl-CoA carboxylase (ACCace) inhibitors such as trionoxime-based and aryloxyphenoxypropionic acid-based herbicides has been imparted by classical breeding methods. .. Useful plants conferred resistance to acetyl-CoA carboxylase (ACCace) inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. It is described in Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990) and the like. Mutant acetyl-CoA carboxylase (ACCace) resistant to acetyl-CoA carboxylase (ACCace) inhibitors has been reported in Weed Science, Vol. 53, pp.
  • a plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a gene into a plant by gene recombination technique or by introducing a mutation involved in imparting resistance into a crop acetyl-CoA carboxylase (ACCCace). Furthermore, a base substitution mutation-introduced nucleic acid represented by chimera plasti technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) is introduced into a plant cell to produce a crop (acetyl CoA carboxylase (acetyl CoA carboxylase). By inducing site-specific amino acid substitution mutations in the ACCace) / herbicide target) gene, plants resistant to acetyl CoA carboxylase (ACCace) inhibitors / herbicides can be created.
  • Examples of useful plants that have been endowed with resistance by gene recombination technology include glyphosate-resistant corn, soybean, cotton, rapeseed, tensai, and alfalfa varieties, Roundup Ready ⁇ registered trademark>, Roundup Lady 2. (Roundup Ready 2) ⁇ Registered Trademark>, Agrisure-GT (AgrisureGT) ⁇ Registered Trademark>, etc. are already on sale. Similarly, there are glufosinate-resistant corn, soybean, cotton, and rapeseed varieties produced by genetic recombination technology, which are already sold under trade names such as LibertyLink (registered trademark).
  • bromoxynil-resistant cotton produced by gene recombination technology is already sold under the trade name of BXN.
  • soybeans resistant to HPPD inhibitors by genetic recombination technology are trade names of Herbicide-tolerant Soybean line as varieties resistant to mesotrione and glufosinate, and Credenz as varieties resistant to HPPD inhibitors, glyphosate and glufosinate.
  • Product names such as ⁇ registered trademark>.
  • 2,4-D or ACCase inhibitor-resistant corn, soybean, and cotton produced by genetically modified technology are already sold under trade names such as Enlist (registered trademark).
  • soybeans resistant to dicamba by genetically modified technology are already sold under trade names such as Roundup Ready 2 Xtend ⁇ registered trademark> as varieties resistant to dicamba and glyphosate.
  • a soybean variety that is resistant to HPPD inhibitors such as isoxaflutol and also resistant to nematodes due to HPPD inhibitor resistance by genetic recombination technology has been registered as GMB151 in the United States.
  • ALS-inhibiting herbicides eg, sulfonylurea herbicides, or imidazolinone herbicides
  • canola corn, corn, millet, corn, cotton, millet, lettuce, lens bean, melon, awa, oat,
  • nata potato, rice, lime, sorghum, soybean, tensai, sunflower, tobacco, tomato and wheat
  • US5013659, WO2006 / 0606634, US4761373, US53047332, US621138, US621314 and US6222100 especially for imidazolinone herbicides.
  • Resistant rice is known and has specific mutations in the acetolactyl synthase gene (eg, S653N, S654K, A122T, S653 (At) N, S654 (At) K, A122 (At) T (eg).
  • S653N, S654K, A122T, S653 (At) N, S654 (At) K, A122 (At) T eg.
  • HPPD inhibitory herbicides eg, isoxazole herbicides such as isoxaflutol, triketone herbicides such as sulcotrione, methotrion, and pyrazole herbicides such as pyrazolinete
  • isoxazole herbicides such as isoxaflutol
  • triketone herbicides such as sulcotrione, methotrion
  • pyrazole herbicides such as pyrazolinete
  • sugar cane, rice, corn, tobacco, soybeans, cotton, rapeseed, sugar beet, wheat and potatoes resistant to diketonitrile see, eg, WO2004 / 055911, WO1996 / 38567, WO1997 / 049816 and US6791014), and PPO.
  • Rice “Clearfield ⁇ registered trademark> Rice” that is resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapill and imazamox as plants to which herbicide resistance has been imparted by conventional cultivar improvement technology or genome breeding technology.
  • corn also known as “corn”
  • Rice canola“ Triazine Solarant Canola ”which is resistant to photochemical II inhibitors
  • sorghum“ Igrowth ⁇ registered trademark> which is resistant to imidazolinone herbicides.
  • RTDS sulfonylurea herbicide-resistant canola "SU Canola” ( ⁇ registered trademark>) using rapid cultivar development technology (Rapid Trait Development System, RTDS ⁇ registered trademark>) as a plant to which herbicide resistance has been imparted by genome editing technology.
  • RTDS ⁇ registered trademark> corresponds to the introduction of an oligonucleotide-oriented mutation in a genome editing technique, and is used in a plant via a Gene Repair Orivar cultivar (GRON), that is, a chimeric oligonucleotide of DNA and RNA. It is a technique that can introduce mutations without cutting the DNA.
  • GRON Gene Repair Orivar cultivar
  • herbicide resistance and phytic acid content were reduced by deleting the endogenous gene IPK1 using a zinc finger nuclease.
  • Examples include corn (see, eg, Nature 459, 437-441, 2009) and rice that has been herbicide-tolerated using crisper casnin (see, eg, Rice, 7, 5, 2014).
  • soybean having the properties of the GM rootstock imparted to the scion by using the breeding technique using grafting can be mentioned.
  • Specific examples thereof include soybeans (see Weed Technology 2013, 27, 412) in which non-transgenic soybean scion is imparted with glyphosate resistance using Roundup Ready ⁇ registered trademark> soybean having glyphosate resistance as a rootstock. ..
  • the above-mentioned "useful plant” includes, for example, a plant capable of synthesizing a selective toxin known in the genus Bacillus by using a gene recombination technique.
  • insecticidal toxin expressed in such a recombinant plant examples include insecticidal proteins derived from Bacillus cereus and Bacillus popillia; Cry1Ab and Cry1Ab derived from Bacillus turingiensis. , Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other ⁇ -endotoxins, VIP1, VIP2, VIP3 or VIP3A and other insecticidal proteins; nematode-derived insecticidal proteins; scorpion toxins, spider toxins, bees.
  • Toxins produced by animals such as toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectin; aglutinin; trypsin inhibitors, serine protease inhibitors, patatin, cystatin, protease inhibitors such as papain inhibitors; lysine, Ribosome-inactivating proteins (RIPs) such as corn-RIP, abrin, saporin, briodin; steroid-metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdisteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdison inhibitors; HMG-CoA Examples thereof include reductase; ion channel inhibitors such as sodium channel inhibitors and calcium channel inhibitors; immature hormone esterases; diuretic hormone receptors; stylben synthase; bibenzyl synthase; kitinase; glucanase and the like.
  • RIPs Rib
  • ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry14Ab-1, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34A, Cry34Ab, or Cry35Ab, VIP1 , VIP2, VIP3 or VIP3A and other insecticidal protein hybrid toxins, partially defective toxins, modified toxins.
  • Hybrid toxins are created using recombinant techniques by a new combination of different domains of these proteins.
  • Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin have been replaced.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins include, for example, EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073 and the like. It is described in the patent document of.
  • the toxins contained in these recombinant plants confer resistance to Coleoptera, Diptera, and Lepidopteran pests, in particular.
  • transgenic plants containing one or more insecticidal pest resistance genes and expressing one or more toxins are already known, and some are commercially available. Examples of these recombinant plants include YieldGard ⁇ registered trademark> (corn varieties expressing Cry1Ab toxin), YieldGuard Rootworm ⁇ registered trademark> (corn varieties expressing Cry3Bb1 toxin), and so on.
  • the above-mentioned useful plants include those imparted with the ability to produce an antipathogenic substance having a selective action by using a gene recombination technique.
  • anti-pathogenic substances examples include PR proteins (described in PRPs, EP-A-03922225); sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.).
  • Ion channel inhibitors such as (stilben synthase; bibenzyl synthase; chitinase; glucanase; peptide antibiotics, antibiotics with heterocycles, protein factors involved in plant disease resistance (called plant disease resistance genes)
  • plant disease resistance genes examples thereof include substances produced by microorganisms such as (described in WO03 / 000906).
  • Such anti-pathogenic substances and the genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191 and the like.
  • the above-mentioned useful plants include crops to which useful traits such as oil component modification and amino acid content enhancing traits have been imparted by using gene recombination technology.
  • useful traits such as oil component modification and amino acid content enhancing traits have been imparted by using gene recombination technology.
  • Examples thereof include VISTIVE ⁇ registered trademark> (low linolene soybean with reduced linolene content), high-lysine (high foil) corn (corn with increased lysine or oil content), and the like.
  • the above-mentioned useful plants include crops that have been imparted with useful traits such as drought tolerance by using genetic recombination technology to maintain or increase the yield.
  • useful traits such as drought tolerance by using genetic recombination technology to maintain or increase the yield.
  • useful traits such as drought tolerance by using genetic recombination technology to maintain or increase the yield.
  • Examples thereof include DrughhtGard ⁇ registered trademark> (corn imparted with drying resistance) and the like.
  • the herbicide of the present invention also exhibits a control effect on the pests and the like exemplified above, which have acquired resistance to existing herbicides.
  • the herbicide of the present invention can also be used for plants that have acquired characteristics such as pest resistance, disease resistance, and herbicide resistance by genetic recombination, artificial mating, and the like.
  • the "plant to which resistance has been imparted by a breeding method or gene recombination technique" of the present invention is not only resistance conferred by classical breeding and resistance conferring by gene recombination technology, but also molecular biology in conventional mating techniques. Includes plants that have been endowed with resistance by a new breeding technology (New Plant Breeding Technologies, NBTs) that combines these methods.
  • New breeding techniques (NBTs) are the book “Let's understand new plant breeding techniques” (International Literature, Ryo Osawa, Hiroshi Egami), review article “Genome Editing Tools in Plants” (Genes 2017, 8, 399, Tapan Kumar Mohanta).
  • Genome breeding technology is a technology for improving the efficiency of breeding using genomic information, and includes DNA marker (also called genomic marker or gene marker) breeding technology and genomic selection.
  • DNA marker breeding is a method of selecting a progeny having a desired useful trait gene from a large number of mating progeny using a DNA marker which is a DNA sequence that serves as a marker for the position of a specific useful trait gene on the genome. be. By analyzing the mating progeny using DNA markers when they are young plants, it has the characteristic that the time required for breeding can be effectively shortened.
  • genomic selection is a method of creating a prediction formula from the phenotype and genomic information obtained in advance, and predicting the characteristics from the prediction formula and genomic information without evaluating the phenotype, which contributes to the efficiency of breeding. It is a possible technology.
  • New breeding technology (new breeding techniques) is a general term for breeding technology that combines molecular biological techniques. For example, sysgenesis / intragenesis, oligonucleotide-oriented mutagenesis, RNA-dependent DNA methylation, genome editing, grafting to GM rootstock or scion, reverse breeding, agroinfiltration, seed production technology (Seed Production).
  • technologies such as Technology (SPT).
  • Genome editing technology is a technology for converting genetic information in a sequence-specific manner, and can delete a base sequence, replace an amino acid sequence, introduce a foreign gene, or the like.
  • tools for example, zinc finger nucleases (Zinc-Finer Nucleases, ZFN, ZFNs) capable of sequence-specific cleavage, TALEN, CRISPR / Cas9, and CRISPR / CRISPR / Cpf1) and Meganuclease.
  • sequence-specific genome modification techniques such as CAS9 nickase and Target-AID prepared by modifying the above-mentioned tools.
  • useful traits such as the above-mentioned classical herbicide traits or herbicide resistance genes, insecticidal pest resistance genes, antipathogenic substance production genes, oil component modification, amino acid content enhancing traits, and drought resistance traits. , Stack varieties that combine multiple of these are also included.
  • Non-agricultural land as a usage scene of the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention includes, for example, embankment slope, riverbed, road shoulder and slope, railroad floor, park green land, ground. , Parking lots, airports, industrial land such as factories and storage facilities, fallow land, or non-agricultural land that needs to control the growth of weeds such as fallow in the city, or orchards, pastures, lawns. , Forestry land, rivers, waterways, canals, reservoirs, etc.
  • the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention have a herbicidal effect on various weeds.
  • the weeds are illustrated below, but are not limited to these examples.
  • Urticaceae Urticaceae: Small Nettle (Urtica urens).
  • Polygonaceae Polygonaceae: ⁇ (Polygonum convolvulus) ⁇ (Polygonum lapathifolium) ⁇ (Polygonum pensylvanicum) ⁇ (Polygonum persicaria) ⁇ (Polygonum longisetum) ⁇ (Polygonum aviculare) ⁇ (Polygonum arenastrum) ⁇ (Polygonum cuspidatum) ⁇ Prostrate knotweed (Rumex japonicus), Prostrate knotweed (Rumex crispus), Prostrate knotweed (Rumex obtusifolius), Suiva (Rumex acetosa), Knotweed (Rumex acetosella), Knotweed.
  • Portulacaceae Portulaca oleracea.
  • Caryophyllaceae Chickweed (Stellaria media), Giant Chickweed (Stellaria aquatica), Mouse-ears (Cerastium holosteoides), Sticky mouse-ear (Cerastium glomeratum), Otsumexa (Spergalina seri)
  • Molluginaceae Car Bazakurosou (Mollugo verticillata).
  • Papaveraceae Poppy (Papaver rhoeas), Papaver dubium (Papaver dubium), Prickly poppy (Argemone Mexicana).
  • Brassicaceae Yellowcresses (Raphanus raphanistrum), Radish (Raphanus sativus), Yellowcresses (Sinapis arvensis), Yellowcresses (Capsella bursa-pastoris), Yellowcresses (Brassica bassa) Descurainia pinnata) ⁇ (Rorippa islandica) ⁇ (Rorippa sylvestris) ⁇ (Thlaspi arvense) ⁇ (Myagrum rugosum) ⁇ (Lepidium virginicum) ⁇ (Coronopus didymus) ⁇ (Descurarinia sophia) , Yellowcresses (Rorippa indica), Yellowcresses (Simnrim office), Yellowcresses (Cardamine flexuosa), Yellowcresses (Nastrutum office), Yellowcresses (Drabane).
  • Creome affinis Creome affinis
  • Legumes Fabaceae: ⁇ (Aeschynomene indica) ⁇ (Aeschynom enerudis) ⁇ (Aeschynomene denticulata) ⁇ (Aeschynomene rudis) ⁇ (Sesbania exaltata) ⁇ (Cassia obtusifolia) ⁇ (Cassia occidentalis ) ⁇ (Desmodium tortuosum) ⁇ (Desmodium adscendens) ⁇ (Desmodium illinoense) ⁇ (Trifolium repens) ⁇ (Pueraria lobata) ⁇ (Vicia angustifolia) ⁇ (Indigofera hirsuta) ⁇ Aeschynomene (Indigofera turuxillensis), Sassage (Vigna sinensis), Crotalaria incana, Okarasuno pea (Vicia siva), Common Vetch (Vetch) , Umago palm (Medicago polymorpha).
  • Oxalidaceae Oxalis corniculata, Oxalis strica, Oxalis oxyptera, Oxalis debilis.
  • Geraniaceae American geranium (Geranium carolinense), Dutch crane's-football (Erodium caturium), Dove's Foot Crane's-bill (Geranium molle), Hedgerow Crabe's-bill (Geranium pyrena).
  • Euphorbiaceae Euphorbiaceae: ⁇ (Euphorbia helioscopia) ⁇ (Euphorbia maculata) ⁇ (Euphorbia hum istrata) ⁇ (Euphorbia esula) ⁇ (Euphorbia heterophylla) ⁇ (Euphorbia brasiliensis) ⁇ (Acalypha australis) ⁇ (Croton glandulosus) ⁇ (Croton lobatus) ⁇ (Phyllanthus corcovadensis) ⁇ (Ricinus com m unis) ⁇ (Astraea lobata) ⁇ (Chamaesyce hirta) ⁇ (Chamaesyce hyssopifolia) ..
  • Sterculiaceae Kobanbanoki (Waltheria indica) Violaceae: Violet arvensis, wild pansy (Viola tricolor).
  • Cucurbitaceae Bur-cucumber (Sicyos angulatus), wild cucumber (Echinocystis lobata), bitter melon (Momodica charantia).
  • Lythraceae Lythrum anceps (Ammannaia multiflora), Nangoku lythraceae (Ammannaia auriculata), Lythrum anceps (Ammannaia coccinea), Purple Loosestrife (Lythrum salicaria), Rotala indica.
  • Elatinaceae Elatinaceae: Elatine triandra, California water wort (Elatine triandra).
  • Umbelliferae weeds (Apiaceae): Auction (Oenanthe javanica), wild carrot (Daucus carrota), poison hemlock (Conumm aculatum), pineapple (Cyclospermum leptophyllum).
  • Araliaceae Hydrocotyle sibthorpioides, Brazilian water pennyworts (Hydrocotyle ranunculoides).
  • Ceratophyllaceae Ceratophyllaceae: Coontail (Ceratophyllum demersum).
  • Haloragis aceae Parrot's feather (Myriophyllum aquaticum), watermilfoils (Myriophyllum verticillatum), Myriophyllum matogrossense, watermilfoils (Myriophyllum lyllum), watermilfoils, etc.
  • Sapindaceae Balloon vine (Cardiospermum halicacabum).
  • Asclepiaceae Milkweed (Asclepias syriaca), Honey Vine Milkweed (Amplamus albidus).
  • Rubiaceae Cleavers (Galium spurium), Galium (Galium spurium var. Echinospermon), Hiroha Futabumgra (Spermacoce latifolia), Hexasepalum vulgaris (Diodella teres), Brazilian Hashikagu
  • Convolvulaceae Weeds (Convolvulaceae): ⁇ (Ipomoea nil) ⁇ (Ipomoea hederacea) ⁇ (Ipomoea purpurea) ⁇ (Ipomoea hederacea var. integriuscula) ⁇ (Ipomoea lacunosa) ⁇ (Ipomoea triloba) ⁇ (Ipooea acuminata) ⁇ (Ipomoea hederifolia) ⁇ (Ipomoea coccinea) ⁇ (Ipomoea quamoclit) ⁇ ⁇ (Ipomoea grandifolia) ⁇ ⁇ (Ipomoea aristolochiafolia) ⁇ (Ipomoea cairica) ⁇ (Convolvulus arvensis) , Kohilgao (Calystegia hederacea), Hilgao (Calystegia japonica), Tsutanoha hirugao (
  • Boraginaceae Forget-me-nots (Myosotis arvensis), Myosotis arvensis, Inumurasaki (Lithospermum office), Shazenmurasaki (Echium plantagineum), Nanbanrurisou (Helio).
  • Solanaceae Nightshade (Datra stramonium), nightshade (Solanum nigrum), nightshade (Solanum americanum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum), nightshade (Solanum ptychanthum) Wild tomato (Solanum sisym briifolia), Warnasubi (Solanum carolinense), Sennarihozuki (Physalis angulata), Smooth grand cherry (Physalis subglabrata), Osennari (Nicandra).
  • Linderniaceae Lindernia procumbens, American Lindernia procumbens, Lindernia procumbens.
  • Plantainaceae ⁇ (Plantago asiatica) ⁇ (Plantago lanceolata) ⁇ (Plantago major) ⁇ (Callitriche palustris) ⁇ (Limnophila sessiliflora) ⁇ (Dopatrium junceum) ⁇ (Gratiola japonica) ⁇ (Bacopa rotundifolia) ⁇ (Veronica hederaefolia), Persian speedwell (Veronica persica), Corn speedwell (Veronica arvensis), Water hyssop (Veronica anagallis-aquatica), Plantagotomenta.
  • Water-plantain weeds (Alismataceae): ⁇ (Sagittaria pygmaea) ⁇ (Sagittaria trifolia) ⁇ (Sagittaria sagittifolia) ⁇ (Sagittaria montevidensis) ⁇ (Sagittaria aginashi) ⁇ (Alisma canaliculatum) ⁇ (Alisma plantago- aquatica) ⁇
  • Hydrocharitaceae Hydrocharitaceae: Frogbit (Limnobium spongia), waterthyme (Hydrilla verticillata), common water nymph (Najas gudalapensis), Egeria densa.
  • Araceae Pistia stratiotes.
  • Pondweed weeds Potamogetonaceae: Potamogeton discinctus, Pondweeds (Potamogetoncrispus, Potamogeton illinoensis, Stickenia pectinata, etc.).
  • Pontederiaceae weeds Water hyacinth (Eichornia crascipes), American konagi (Heteranthera limosa), Monochoria korsakowii, Konagi (Monochoria vaginalis), Heterandera reniformis.
  • Commelinaceae begins a plant: Dayflower (Commelina communis), Commelina benghalensis, Electdayflower (Commelina erecta), Murdannia keisak, Doveweed (Murdannia).
  • Commelinaceae Dayflower (Commelina communis), Commelina benghalensis, Electdayflower (Commelina erecta), Murdannia keisak, Doveweed (Murdannia).
  • Poaceae Poaceae: Inubie (Echinochloa crus-galli), Tainubier (Echinochloa oryzicola), Himeta barnyardgrass (Echinochloa crus-galli var formosensis), Late water glass (Echinochloa oryzo) (Setaria viridis), Aquino enacologsa (Setaria faveri), Kinenokoro (Setaria grauca), American enocologsa (Setaria geniculata), Mexican barnyardgrass (Digitaria guiliaris) Digitaria insularis) ⁇ (Eleusine indica) ⁇ (Poa annua) ⁇ (Poa trivialis) ⁇ (Poa pratensis) ⁇ (Alospecurus aequalis) ⁇ (Alopecurus myosuroides) ⁇ (Avena fatua) ⁇ (Sorghum halepense), Shattercane (Sorghum bulgare), S
  • Equisetaceae Equisetaceae: Horsetail (Equisetum palustre), Equisetum palustre.
  • Salvinia seaweed Salvinia natans.
  • Azollaceae Azolla japonica, Azollaim bricata, Salvinia natanas, Azolla cristata.
  • Ricciaceae Ricciocarpos natans.
  • Rosaceae Lady's mantle (Alchemilla monticola).
  • Ranunculaceae Ranunculus silicatus, Ranunculus sardous.
  • Eriocaulaceae Eriocaulon cinereum.
  • the variation within the species is not particularly limited. That is, those having reduced sensitivity to a specific herbicide (also referred to as exhibiting resistance) are also included.
  • the decrease in susceptibility may be due to a mutation at the target site (point mutation) or a factor other than the point mutation (non-point mutation).
  • point of action mutations mutations in the nucleic acid sequence portion (open reading frame) corresponding to the amino acid sequence of the protein cause amino acid substitution in the protein at the target site, deletion of the suppressor sequence in the promoter region, and enhancer sequence. This includes those in which the protein at the target site is expressed in excess or decrease due to amplification of the gene or mutation such as increase or decrease in the number of copies of the gene.
  • Non-point mutations include metabolic enhancement, absorption deficiency, subsequent deficiency, and extrasystem excretion.
  • Factors that enhance metabolism include those with increased activity of metabolic enzymes such as cytochrome P450 monooxygenase, arylacylamidase, esterase, and glutathione S-transferase.
  • Out-of-system discharge includes transport to vacuoles by an ABC transporter.
  • herbicide-resistant weeds include 5-enolpyrvir simirate-3-phosphate (EPSP) synthase inhibitor resistance such as glyphosate, and hormonal-disrupting herbicides such as 2,4-D and dicamba.
  • EPP 5-enolpyrvir simirate-3-phosphate
  • ALS acetolactic synthase
  • ACCace acetyl CoA carboxylase
  • PPO protoporphyllinogen oxidase
  • auxin herbicide resistance 4-hydroxy Phenylpyruvate dioxygenase (4-HPPD) inhibitor resistance, photochemical system II inhibitor resistance, photochemical system I electron converter resistance, carotenoid biosynthesis inhibitor resistance, glutamine synthase inhibitor resistance, phytoene elimination Saturated enzyme system (PDS) inhibitor resistance, fatty acid biosynthesis inhibitor resistance, ultra-long chain fatty acid elongation enzyme (VLCFAE) inhibitor resistance, auxin transport inhibitor resistance, dihydropteroic acid (DHP) synthase Inhibitor resistance
  • Resistant weeds are two or more of the above groups (2 groups arbitrarily selected, 3 groups arbitrarily selected, 4 groups arbitrarily selected, 5 groups, 6 groups, 7 groups arbitrarily selected, Even resistant weeds (stacked) that also have resistance to (group 8) are effectively controlled.
  • Examples of stacked resistant weeds are acetolactic synthase (ALS) inhibitors, protoporphyllinogen oxidase (PPO) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitors, photochemical system II.
  • Inhibitors and water hemps resistant to all of 2,4-D are known, but they are also effectively controlled.
  • the above stack may be a combination of action point mutations, a combination of non-point mutations, or a combination of action mutations and non-point mutations.
  • the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention are simultaneously or divided into useful plants, places where useful plants are to be grown or where they are growing, or non-agricultural land. When applying, apply once or multiple times. Weeds may have already grown in the plant or the plant cultivated area, or may be before the outbreak.
  • the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention are simultaneously or divided into useful plants, places where useful plants are to be grown or where they are growing, or non-agricultural land.
  • Examples of the method of application include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment, seed treatment and hydroponic liquid treatment.
  • foliage treatment for example, a pesticide composition containing the herbicide of the present invention and the herbicide of the present invention can be applied to foliage, tree stems, fruits, flowers (including before, during, and after flowering), ears, or the entire plant. There is a method of treating the surface of.
  • Examples of soil treatment include soil spraying, soil miscibility, and chemical irrigation into the soil.
  • places for soil treatment for example, planting holes, crops, near planting holes, near crops, the entire cultivation area, near the plant area, between stocks, under the trunk, main trunk ridges, soil cultivation, nursery boxes, seedling raising. Examples include trays and nurseries.
  • Examples of the treatment time include pre-sowing, sowing, post-sowing, seedling raising period, pre-planting, planting, and post-sowing growing period.
  • the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention may be mixed with the irrigation liquid, for example, to an irrigation facility (irrigation tube, irrigation pipe, sprinkler, etc.). Injection, mixing in interstitial flooded liquid, mixing in hydroponic liquid, etc. can be mentioned.
  • the irrigation solution and the active ingredient can be mixed in advance and treated by using, for example, the above irrigation method or an appropriate irrigation method such as watering or flooding.
  • the root treatment includes, for example, a method of immersing the root in a chemical solution containing the herbicide of the present invention and a pesticide composition containing the herbicide of the present invention, and a pesticide composition containing the herbicide of the present invention and the herbicide of the present invention. Examples thereof include a method of adhering a solid preparation containing a substance to the root of a plant.
  • Examples of the shower treatment include a method of showering a diluted solution of a pesticide composition containing the herbicide of the present invention and the herbicide of the present invention on the foliage of a plant.
  • Examples of the smoke treatment include a method in which a diluted solution of the herbicide of the present invention and a pesticide composition containing the herbicide of the present invention is made into a mist and scattered in the air to adhere to the foliage of a plant or the like. ..
  • Examples of the water surface treatment include a method of spraying a chemical solution or a solid preparation containing the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention on a paddy field in a flooded state.
  • Examples of the seed treatment include treatment of the herbicide of the present invention on seeds or vegetative reproduction organs and the treatment of a pesticide composition containing the herbicide of the present invention.
  • the above-mentioned vegetative organs include seed potatoes in particular.
  • the hydroponic solution treatment is, for example, a method of mixing or mixing a chemical solution or a solid preparation containing the herbicide of the present invention and a pesticide composition containing the herbicide of the present invention with the hydroponic solution (hydroponic solution miscibility treatment, water). Treatment of mixing cultivated liquid, etc.) and the like.
  • the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention can also be applied by spot treatment.
  • Spot treatment is a concept opposite to the uniform treatment of the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention, and is a place where weeds are growing or where weeds are generated. It means a treatment of selectively spraying the herbicide of the present invention and the pesticide composition containing the herbicide of the present invention to a possible place.
  • treating to a place is meant treating a plant or soil that has or may have weeds.
  • spot treatment is not considered only when all of the places where weeds are growing or where weeds may grow in a continuous cultivation area are selectively treated.
  • the herbicide of the present invention and the herbicide of the present invention are used. Even if it is not treated with the pesticide composition containing it, it is included in the spot treatment if there is a spot-treated place in the continuous cultivation area.
  • the melting point which is the physical property value of the compound of the present invention, was measured with an MP-500V trace melting point measuring device manufactured by Yanaco.
  • the refractive index was measured using an Abbe refractometer manufactured by Atago. 1
  • the 1 H NMR spectrum was measured using JEM-LA400 (400 MHz) or JNM-ECS300 (300 MHz) manufactured by JEOL Ltd. with tetramethylsilane (TMS) as an internal standard.
  • N- [2,6-bis (methoxymethoxy) phenyl] -N- ⁇ 2- [3- (trifluoromethyl) -1H-pyrazole-1-yl] ethyl ⁇ formamide N- [2,6-bis (methoxymethoxy) phenyl] formamide 0.60 g (2.49 mmol), 1- (2-bromoethyl) -3- (trifluoromethyl) -1H-pyrazole 0.85 g (3.50 mmol) ), To a mixture of 10 mL of N, N-dimethylformamide, 0.30 g of sodium hydride (7.50 mmol, converted as 60% purity) was added at room temperature, and the mixture was stirred at 40 ° C.
  • Example 12 4-[(5-Chloropyrimidine-2-yl) oxy] -1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazole-2- Manufacture of ON (compound number of the present invention: H-0003): (1) Production of 4-Methoxy-1-methyl-3- (4,4,4-trifluorobutyl) -1,3-dihydro-2H-benzo [d] imidazole-2-one: 4-Methoxy-1-methyl-1,3-dihydro-2H-benzo [d] imidazol-2-one 0.60 g (3.37 mmol), 1,1,1-trifluoro-4-iodobutane 1.12 g ( A mixture of 4.71 mmol), 0.70 g (5.07 mmol) of potassium carbonate and 10 mL of N, N-dimethylformamide was stirred at 70 ° C.
  • Granule wettable powder 10 parts of each compound shown in Tables 1 to 37 and Tables 38 to 54 5 parts of sodium lignin sulfonate 5 parts of polyoxyethylene alkylaryl ether 1 part of sodium polycarboxylate 3 parts of white carbon 5 Part 1 part of pregelatinized starch 1 part of calcium carbonate 65 parts of water 10 parts or more of water was mixed and kneaded and granulated. The obtained granules were dried in a fluidized bed dryer to obtain a granule wettable powder.
  • Test for confirming herbicidal activity against barnyard grass in foliage treatment Field soil was filled in a plastic pot of about 340 cm and 3 volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compounds that had a herbicidal effect on barnyard grass in the foliage treatment were compounds A-0004, A-0015, A-0041, B-0008, B-0152, B-0153, B-0154, B-0156, B. -0157, B-0158, B-0162, B-0221, B-0245, B-0247, B-0273, B-0275, B-0301, B-0303, B-034, B-0305, B-0307 , B-0309, B-0310, B-0311, B-0314, B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B -0359, B-0368, B-0369, B-0370, B-0372, B-0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405 , B-0409, B-0441, B-04
  • Test for confirming herbicidal activity against Festuca perensis in foliage treatment The field soil was filled in a plastic pot of about 340 cm and 3 volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compounds that had a herbicidal effect on Festuca perennial in the foliage treatment were Compounds A-0032, B-0008, B-00908, B-0152, B-0153, B-0154, B-0156, B-0158, B. -0162, B-0221, B-0245, B-0247, B-0273, B-0276, B-0301, B-0303, B-0304, B-0309, B-0310, B-0311, B-0314 , B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0359, B-0368, B-0369, B-0370, B-0372, B -0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B-0448, B-0461, B-0462, B-0466 , B-0468, B-0469, B-04
  • the compounds that had a herbicidal effect on velvetleaf by foliar spraying were compounds A-0004, A-0007, A-0015, A-0032, A-0036, A-0041, A-0065, A-0066, B.
  • Test for confirming herbicidal activity against Amaranthus retroflexa in foliage treatment The field soil was filled in a plastic pot of about 340 cm and 3 volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compounds that had a herbicidal effect on Amaranthus retroflexa in the foliage treatment were compounds A-0002, A-0004, A-0007, A-0015, A-0032, A-0036, A-0041, A-0065, A.
  • Test for confirming herbicidal activity against barnyard grass in soil treatment Field soil was filled in a plastic pot of about 340 cm and 3 volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm.
  • the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • Compounds that had a herbicidal effect on barnyard grass in soil treatment were compounds A-0001, A-0004, A-0015, A-0032, A-0036, A-0041, A-0065, B-0008, B. -0898, B-0152, B-0153, B-0154, B-0156, B-0157, B-0158, B-0160, B-0162, B-0221, B-0245, B-0247, B-0266 , B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B-0310, B-0311, B-0314, B -0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B-0372 , B-0376, B-0377
  • Test for confirming herbicidal activity against Festuca perensis in soil treatment The field soil was filled in a plastic pot of about 340 cm and 3 volumes, and the seeds of Festuca perennial were sown at a sowing depth of 1 cm.
  • the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • Compounds that had a herbicidal effect on Festuca perennial in soil treatment were compounds A-0004, A-0015, A-0032, A-0036, A-0041, B-0008, B-00908, B-0152, B. -0153, B-0154, B-0156, B-0157, B-0158, B-0162, B-0221, B-0245, B-0247, B-0266, B-0273, B-0275, B-0276 , B-0301, B-0303, B-0304, B-0305, B-0307, B-0309, B-0310, B-0311, B-0314, B-0325, B-0327, B-0328, B -0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B-0372, B-0374, B-0376, B-0377 , B-0384, B-
  • Compounds that had a herbicidal effect on velvetleaf in soil treatment were compounds A-0036, A-0041, B-0008, B-00908, B-0152, B-0153, B-0158, B-0221, B. -0245, B-0247, B-0266, B-0273, B-0275, B-0276, B-0301, B-0303, B-0304, B-0309, B-0310, B-0311, B-0314 , B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0368, B-0369, B-0370, B -0376, B-0377, B-0384, B-0387, B-0389, B-0403, B-0409, B-0448, B-0461, B-0462, B-0468, B-0469, B-0493 , B-0499, B-0514,
  • Test for confirming herbicidal activity against Amaranthus retroflexus in soil treatment Field soil was filled in a plastic pot of about 340 cm and 3 volumes, and Amaranthus retroflexa seeds were sown at a sowing depth of 1 cm.
  • the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • Compounds that had a herbicidal effect on Amaranthus retroflexa in soil treatment were compounds A-0004, A-0015, A-0032, A-0036, A-0041, A-0065, B-0008, B-00908, B.
  • B-0305 B-0307, B-0309, B-0310, B-0311, B-0314, B -0316, B-0325, B-0327, B-0328, B-0333, B-0334, B-0338, B-0342, B-0350, B-0359, B-0362, B-0368, B-0369 , B-0370, B-0372, B-0374, B-0376, B-0377, B-0384, B-0387, B-0389, B-0399, B-0403, B-0405, B-0409, B -0438, B-0441, B-0448,
  • Test for confirming herbicidal activity against barnyard grass in foliage treatment Field soil was filled in a plastic pot of about 3020 cm 3 volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm and cultivated in a greenhouse. After about 2 weeks, the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 250 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer. The foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compound that had a herbicidal effect on barnyard grass in the foliage treatment was compound B-0536.
  • the compound that had a herbicidal effect on velvetleaf in the foliage treatment was compound B-0536.
  • Test for confirming herbicidal activity against barnyard grass in soil treatment Field soil was filled in a plastic pot of about 3020 cm 3 volumes, and barnyard grass seeds were sown at a sowing depth of 1 cm.
  • the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 1000 g per hectare, and the equivalent of 1000 liters of water per hectare is applied to the entire surface of the soil with a small sprayer. It was sprayed. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compound that had a herbicidal effect on barnyard grass in soil treatment was compound B-0536.
  • the compound that had a herbicidal effect on velvetleaf in soil treatment was compound B-0536.
  • Test for confirming herbicidal activity against barnyard grass in a hydroponic test Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then pour 8 ml of Inubier seeds on the cotton surface. was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.
  • the compounds that had a herbicidal effect on barnyard grass were compounds A-0067, B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0117, E-0207, E-0213, E-0223, E-0240, E- They were 0249, E-0257, E-0260, E-0276, E-0403, E-0420, and G-0051.
  • Test for confirming herbicidal activity against Festuca perensis in a hydroponic test Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then pour 8 ml of rat seeds on the cotton surface. was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.
  • the compounds that had a herbicidal effect on Festuca perennial were compounds A-0067, B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0170, E-0189, E-0197, E-0207, E-0213, E- They were 0223, E-0240, E-0249, E-0257, E-0276, E-0403, E-0420, and G-0051.
  • the compounds that had a herbicidal effect on lettuce were compounds A-0067, B-0342, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0207, E-0240, E-0249, E-0257, E-0276, E-0403, E- It was 0420 and G-0051.
  • Test for confirming herbicidal activity against Amaranthus retroflexus in a hydroponic test Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then pour 8 ml of Amaranthus retroflexa seeds on the cotton surface.
  • the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.
  • the compounds that had a herbicidal effect on Amaranthus retroflexa were compounds A-0067, B-0342, B-0560, B-0563, D-0010, D-0011, D-0020, D-0021, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0117, E-0147, E-0189, E-0197, E- They were 0207, E-0213, E-0223, E-0240, E-0249, E-0257, E-0260, E-0266, E-0276, E-0403, E-0420, and G-0051.
  • Test for confirming herbicidal activity against dog firefly in a hydroponic test Spread cotton in a 60 ml plastic cup, dilute 8 ml of the wettable powder adjusted according to Pharmaceutical Example 2 with water so that the concentration of the test compound becomes 200 ppm, and then pour 8 ml of it, and then inu firefly seeds on the cotton surface. was sown. After closing the lid, the cultivation was continued under the conditions of 12 hours light period / 12 hours dark period and about 20 ° C. by irradiation with a fluorescent lamp, and the herbicidal effect was confirmed about 7 days after the treatment.
  • the compounds that had a herbicidal effect on dog firefly were compounds A-0067, B-0342, B-0563, D-0010, D-0011, D-0020, E-0001, E-0052, E-0074, E-0906, E-0106, E-0108, E-0109, E-0111, E-0117, E-0189, E-0207, E-0213, E-0223, E-0240, E- They were 0249, E-0257, E-0260, E-0266, E-0276, E-0403, E-0420, and G-0051.
  • the compound superior to the compounds B-0152, B-0153, B-0154, B-0156 and B-0462 in the herbicidal effect on the rat wheat was compound B-0245.
  • the compound superior to the compounds B-0154, B-0156 and B-0462 in the herbicidal effect on velvetleaf was compound B-0245.
  • the compound superior to the compound B-034 in the herbicidal effect on the rat wheat was the compound B-0309.
  • the compound superior to the compounds B-0328 and B-0469 in the herbicidal effect on the rat wheat was the compound B-0544.
  • the compounds superior to compound B-0328 in the herbicidal effect on velvetleaf in the foliage treatment were compounds B-0333 and B-0544.
  • the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer.
  • the foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on the rat wheat were the compounds B-0333 and B-0544.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on velvetleaf were the compounds B-0333 and B-0544.
  • the compound superior to the compounds B-0152, B-0156 and B-0462 in the herbicidal effect on oats was compound B-0245.
  • the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer.
  • the foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compound superior to the compounds B-0152, B-0153, B-0156 and B-0462 in the herbicidal effect on Alopecurus aequalis was compound B-0245.
  • the compound superior to the compounds B-0152 and B-0156 in the herbicidal effect on Oinutade was compound B-0245.
  • the compound superior to the compounds B-0152, B-0153, B-0156 and B-0462 in the herbicidal effect on white goosefoot was compound B-0245.
  • the compound superior to the compounds B-0152, B-0156 and B-0462 in the herbicidal effect on velvetleaf was compound B-0245.
  • the compound superior to the compounds B-0152, B-0153, B-0156 and B-0462 in the herbicidal effect on the morning glory was compound B-0245.
  • the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer.
  • the foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compound superior to the compound B-034 in the herbicidal effect on the morning glory was the compound B-0309.
  • the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer.
  • the foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on barnyard grass were the compounds B-0333 and B-0544.
  • the wettable powder adjusted according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g per hectare, and the amount equivalent to 1000 liters of sprayed water per hectare is applied to a small sprayer.
  • the foliage was sprayed on the weeds in the pot. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on white goosefoot were the compounds B-0333 and B-0544.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on velvetleaf were the compounds B-0333 and B-0544.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on the morning glory were the compounds B-0333 and B-0544.
  • the compounds superior to the compounds B-0328 and B-0469 in the herbicidal effect on Amaranthus palmeri were the compounds B-0333 and B-0544.
  • the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 63 g or 16 g per hectare, and the equivalent of 1000 liters of sprayed water per hectare is applied to the soil with a small sprayer. It was sprayed on the entire surface. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • compounds B-0333 and B-0544 were superior to compound B-0328 in herbicidal effect on Alopecurus aequalis.
  • Compounds B-0333 and B-0544 were superior to compound B-0328 in herbicidal effect on soil treatment.
  • the wettable powder prepared according to Pharmaceutical Example 2 is diluted with water so that the dosage of the test compound is 38 g per hectare, and the amount equivalent to 200 liters of water per hectare is applied to the entire surface of the soil with an automatic spraying device. It was sprayed on. After that, the cultivation was continued in the greenhouse, and the herbicidal effect was confirmed about 20 days after the treatment.
  • the present invention provides a novel compound having excellent herbicidal activity and a production intermediate thereof, is useful in the fields of agrochemicals and agriculture, and has the possibility of industrial use.

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  • Wood Science & Technology (AREA)
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  • Agronomy & Crop Science (AREA)
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Abstract

La présente invention concerne un nouveau dérivé hétérocyclique fusionné ou un sel acceptable en agriculture de celui-ci et un herbicide le contenant en tant que principe actif.　L'invention concerne un dérivé hétérocyclique fusionné représenté par la formule générale [I] (dans la formule générale [I], Q représente Q-1, Q-2, Q-3, Q-4, Q-5, Q-6, Q-7 ou Q-8, R7 représente un atome d'halogène, un groupe haloalkyle en C1-C6, un groupe cyano, etc, Z représente un atome d'oxygène ou un atome de soufre, A représente N ou C-R13, R13 représente un atome d'hydrogène, un atome d'halogène ou un groupe cyano) ou un sel de celui-ci et un herbicide caractérisé en ce qu'il contient celui-ci en tant que principe actif.
PCT/JP2021/039485 2020-10-29 2021-10-26 Dérivé hétérocyclique fusionné et herbicide le contenant en tant que principe actif WO2022092084A1 (fr)

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CN115448892A (zh) * 2022-09-19 2022-12-09 郑州铁路职业技术学院 一种苯并噻二唑杂环化合物的合成方法

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CN116569834B (zh) * 2023-06-25 2024-05-24 广西壮族自治区农业科学院 一种提高苦瓜杂交制种产量的方法

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JP2016514669A (ja) * 2013-03-15 2016-05-23 ダウ アグロサイエンシィズ エルエルシー ４−アミノ−６−（複素環）ピコリネートおよび６−アミノ−２−（複素環）ピリミジン−４−カルボキシレートならびに除草剤としてのその使用
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JPH0193584A (ja) * 1987-07-16 1989-04-12 American Cyanamid Co 除草的に活性なアリールオキシ飽和５員ベンゾ融合複素環式化合物
JPH02191263A (ja) * 1988-11-03 1990-07-27 American Cyanamid Co アリーロキシベンゾトリアゾール化合物及びその製造法
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CN115448892A (zh) * 2022-09-19 2022-12-09 郑州铁路职业技术学院 一种苯并噻二唑杂环化合物的合成方法
CN115448892B (zh) * 2022-09-19 2023-07-07 郑州铁路职业技术学院 一种苯并噻二唑杂环化合物的合成方法

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