US 8,076,487 B2 · Pyridone derivative and herbicide

Abstract

A pyridone derivative represented by Formula [1] or an agriculturally acceptable salt thereof: wherein R1 is a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or the like; R2 and R3 are each independently a hydrogen atom, a nitro group, a cyano group, or the like; and A is a group represented by Formula A-1, Formula A-2, Formula A-3, Formula A-4, or Formula A-5: The compounds represented by general formula [1] control various weeds growing in upland fields, orchards, paddy fields, and non-crop lands while showing high safety to useful plants and crops.

A pyridone derivative of Formula [1]:

wherein R1 is:
a C1-6 alkyl group,
a C2-6 alkenyl group,
a C2-6 alkynyl group,
a C3-8 cycloalkyl group,
a C3-8 cycloalkyl C1-6 alkyl group,
a C1-6 haloalkyl group,
a C2-6 haloalkenyl group,
a C2-6 haloalkynyl group,
a C1-6 alkylamino C1-6 alkyl group,
a di(C1-6 alkyl)amino C1-6 alkyl group,
a C1-6 alkylthio C1-6 alkyl group,
a C1-6 alkylsulfinyl C1-6 alkyl group,
a C1-6 alkylsulfonyl C1-6 alkyl group,
a C3-8 cycloalkylthio C1-6 alkyl group,
a C3-8 cycloalkylsulfinyl C1-6 alkyl group,
a C3-8 cycloalkylsulfonyl C1-6 alkyl group,
a C3-8 cycloalkyl C1-6 alkylthio C1-6 alkyl group,
a C3-8 cycloalkyl C1-6 alkylsulfinyl C1-6 alkyl group,
a C3-8 cycloalkyl C1-6 alkylsulfonyl C1-6 alkyl group,
a C2-6 alkenylthio C1-6 alkyl group,
a C2-6 alkenylsulfinyl C1-6 alkyl group,
a C2-6 alkenylsulfonyl C1-6 alkyl group,
a C2-6 alkynylthio C1-6 alkyl group,
a C2-6 alkynylsulfinyl C1-6 alkyl group,
a C2-6 alkynylsulfonyl C1-6 alkyl group,
a C1-6 haloalkylthio C1-6 alkyl group,
a C1-6 haloalkylsulfinyl C1-6 alkyl group,
a C1-6 haloalkylsulfonyl C1-6 alkyl group,
a C1-6 alkoxy C1-6 alkyl group,
a C1-6 alkoxy C1-6 alkoxy C1-6 alkyl group,
a C3-8 cycloalkyloxy C1-6 alkyl group,
a benzyloxy C1-6 alkyl group which may be substituted with one or more substituents selected from Substituent Group α,
a cyano C1-6 alkyl group,
a C1-6 haloalkoxy C1-6 alkyl group,
a phenyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenyl C1-6 alkyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenyl C2-6 alkenyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenyl C2-6 alkynyl group which may be substituted with one or more substituents selected from Substituent Group α,
a C1-6 alkoxyimino C1-6 alkyl group,
a phenoxyimino C1-6 alkyl group which may be substituted with one or more substituents selected from Substituent Group α,
a di(C1-6 alkoxy)C1-6 alkyl group,
a formyl C1-6 alkyl group,
a C2-6 alkylideneamino group,
a di(C1-10 alkyl)amino C1-6 alkylideneamino group,
a NR31R32 group,
a C1-6 alkoxy group,
a C2-6 alkenyloxy group,
a C2-6 alkynyloxy group,
a C3-8 cycloalkyloxy group,
a C3-8 cycloalkyl C1-3 alkyloxy group,
a C1-6 haloalkoxy group,
a C2-10 heterocyclic group having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom (wherein the heterocyclic group is optionally substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups or cyano group),
a C1-6 alkyl group substituted with a C2-10 heterocyclic ring having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom and wherein the C2-10 heterocyclic ring, substituted on the C1-6 alkyl group, is optionally substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups or cyano groups
a C1-6 alkylamino group substituted with a C2-10 heterocyclic ring having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom and wherein the C2-10 heterocyclic ring, substituted on the C1-6 alkylamino group, is optionally substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups or cyano groups), or
a C1-6 alkoxy C1-6 alkyl group substituted with a C2-10 heterocyclic ring having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom and wherein the C2-10 heterocyclic ring, substituted on the C1-6 alkoxy C1-6 alkyl group, is optionally substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups, C1-6 haloalkoxy groups or cyano groups;
wherein R2 and R3 are each independently:
a hydrogen atom,
a nitro group,
a cyano group,
a C1-6 alkyl group,
a C2-6 alkenyl group,
a C2-6 alkynyl group,
a C3-8 cycloalkyl group,
a C1-6 haloalkyl group,
a C2-6 haloalkenyl group,
a C2-6 haloalkynyl group,
a C1-6 alkoxy group,
a C1-6 haloalkoxy group,
a C1-6 alkylthio group,
a C1-6 alkylsulfinyl group,
a C1-6 alkylsulfonyl group,
a C1-6 alkylsulfonyl C1-6 alkyl group,
a C1-6 haloalkylthio group,
a C1-6 haloalkylsulfinyl group,
a C1-6 haloalkylsulfonyl group,
a C1-6 alkoxy C1-6 alkyl group,
a C3-8 cycloalkyloxy C1-4 alkyl group,
a di(C1-6 alkoxy) C1-6 alkyl group,
a phenyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenyl C1-6 alkyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenyl C2-6 alkenyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenyl C2-6 alkynyl group which may be substituted with one or more substituents selected from Substituent Group α, or
a halogen atom;
and
wherein A is selected from the group consisting of Formula A-1, Formula A-2, Formula A-3, Formula A-4, and Formula A-5:
wherein R4 is:
a hydroxyl group,
O−M+ (where M+ represents an alkali metal cation or an ammonium cation),
a halogen atom,
a cyano group,
an isothiocyanate group,
an isocyanate group,
a hydroxycarbonyloxy group,
a C1-6 alkoxycarbonyloxy group,
a benzyloxy carbonyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a C1-12 alkoxy group,
a C2-6 alkenyloxy group,
a C2-6 alknyloxy group,
a C3-6 cycloalkyloxy group,
a cyanomethyleneoxy group,
a C3-8 cycloalkyl C1-3 alkyloxy group,
a C1-8 alkylcarbonyloxy group,
a C1-6 haloalkylcarbonyloxy group,
a C2-6 alkenylcarbonyloxy group,
a C2-6 haloalkenylcarbonyloxy group,
a C2-6 alkynylcarbonyloxy group,
a C2-6 haloalkynylcarbonyloxy group,
a C1-6 alkoxycarbonyl C1-6 alkoxy group,
a phenyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a benzyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a phenylcarbonyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylcarbonyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a phenylcarbonyl C1-6 alkyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a C1-3 alkylsulfonyloxy group,
a phenylsulfonyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylsulfonyloxy group which may be substituted with one or more substituents selected from Substituent Group α,
a C1-10 alkylthio group, a C1-10 alkylsulfinyl group,
a C1-10 alkylsulfonyl group, a phenylthio group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylthio group which may be substituted with one or more substituents selected from Substituent Group α,
a phenylsulfinyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylsulfinyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenylsulfonyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylsulfonyl group which may be substituted with one or more substituents selected from Substituent Group α,
a C1-10 alkylamino group,
a di(C1-10 alkyl)amino group,
a C1-6 alkoxycarbonylamino group,
a C1-6 alkyloxy group substituted with a C2-10 heterocyclic ring having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom, and wherein the C2-10 heterocyclic ring, substituted on the C1-6 alkyloxy group, is optionally substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups or cyano groups, or
a C2-10 heterocyclic group having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom, wherein the C2-10 heterocyclic group is optionally substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-8 haloalkyl groups, C1-6 alkoxy groups or cyano group);
wherein A0 is selected from the group consisting of Formula X10 and Formula X11:
wherein A1 is selected from the group consisting of Formula X1 and Formula X2:
wherein A2 is selected from the group consisting of Formula X3, Formula X4, Formula X5, Formula X6, and Formula X7:
wherein A3 is selected from the group consisting of Formula X8 and Formula X9:
wherein:
n is 0, 1 or 2;
R5, R6, R8, R9, R11 and R12 are each independently a hydrogen atom or a C1-6 alkyl group,
R5 and R8 may form a ring by bonding with a C1-5 alkylene chain or a C2-5 alkenylene chain, or R5 and R11 may form a ring by bonding with a C2-5 alkylene chain or a C2-5 alkenylene chain;
R7, R33, and R34 are each independently a hydrogen atom, a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group or a C1-6 alkoxy group;
R14, R15, R16, and R17 are each independently a hydrogen atom, a C1-6 alkyl group, a C1-6 alkoxy group or a benzyl group which may be substituted with one or more substituents selected from Substituent Group α;
R18 is a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a cyanomethyl group or a benzyl group which may be substituted with one or more substituents selected from Substituent Group α;
R20 is a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-8 cycloalkyl group or a C3-5 cycloalkyl C1-6 alkyl group;
R21 is a hydrogen atom, a C1-6 alkyl group or a halogen atom;
R23 is:
a C1-6 alkyl group,
a C1-6 haloalkyl group,
a C3-8 cycloalkyl group,
a C1-10 alkylthio group,
a C1-10 alkylsulfinyl group,
a C1-10 alkylsulfonyl group,
a phenylthio group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylthio group which may be substituted with one or more substituents selected from Substituent Group α,
a phenylsulfinyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylsulfinyl group which may be substituted with one or more substituents selected from Substituent Group α,
a phenylsulfonyl group which may be substituted with one or more substituents selected from Substituent Group α, or
a benzylsulfonyl group which may be substituted with one or more substituents selected from Substituent Group α;
R24 is a hydrogen atom, a halogen atom, a cyano group, a C1-6 alkyl group, a C3-8 cycloalkyl group, or a C1-6 alkoxycarbonylamino group;
and
R25 is a C1-6 alkoxycarbonyl group, a cyano group or a nitro group, and
R31 and R32 are each independently:
a hydrogen atom,
a C1-6 alkyl group, a phenyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzyl group which may be substituted with one or more substituents selected from Substituent Group α,
a C1-6 alkoxy C1-6 alkyl group,
a C1-6 alkylcarbonyl group,
a C1-6 alkoxycarbonyl group,
a benzyloxycarbonyl group which may be substituted with one or more
substituents selected from Substituent Group α,
a C1-6 haloalkyl group,
a C3-8 cycloalkyl group,
a C3-8 cycloalkyl C1-6 alkyl group,
a C1-6 alkylsulfonyl group,
a phenylsulfonyl group which may be substituted with one or more substituents selected from Substituent Group α,
a benzylsulfonyl group which may be substituted with one or more substituents selected from Substituent Group α,
a C2-10 heterocyclic group having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom and wherein the C2-10 heterocyclic group of R31 and R32 may be substituted with 1 to 5 halogen atoms, oxo groups, C1-6 alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups or cyano groups, or
a C1-6 alkyl group substituted with a C2-10 heterocyclic ring having one or more of the same or different hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom and wherein the C2-10 heterocyclic ring of the C1-6 alkyl group may be substituted with 1 to 5 halogen atoms, oxo groups, alkyl groups, C1-6 haloalkyl groups, C1-6 alkoxy groups or cyano groups, and
wherein Substituent Group α is a halogen atom, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-4 alkylenedioxy group, a nitro group, a cyano group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, a C1-6 alkylsulfonyl group, a C1-6 alkoxy C1-6 alkyl group and a C1-6 haloalkylsulfonylamino group, or an agriculturally acceptable salt thereof.

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Pyridone derivative and herbicide

Life of this patent

Pyridone derivative and herbicide

Life of this patent

Abstract

Claims6