US 8,969,554 B2 · 6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

Abstract

Disclosed are compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides. The compounds are triazine derivatives represented by following Formula 1 or salts thereof, and the herbicides containing them: [Chem. 28] wherein in the formula, R1 represents a hydrogen atom; a C1-C12 alkyl group; a C2-C6 alkenyl group, etc., R2 represents a C1-C12 alkyl group, etc., Y and Z represent an oxygen atom or a sulfur atom, and A represents a 5- or 6-membered cyclic group which may contain a nitrogen atom, an oxygen atom, or a sulfur atom.

A triazine derivative or a salt thereof represented by following Formula 1:

wherein R1 is selected from the group consisting of a hydrogen atom;
a C1-C12 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkenyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
an amino C1-C6 alkyl group;
a nitro C1-C6 alkyl group;
a C1-C6 alkylamino C1-C6 alkyl group;
a di(C1-C6 alkyl)amino C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a hydroxy C1-C6 alkyl group;
a phenyl C1-C6 alkoxy C1-C6 alkyl group wherein said phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α;
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a C3-C6 cycloalkyl C1-C6 alkyloxy C1-C6 alkyl group;
a phenyloxy C1-C6 alkyl group wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylthio C1-C6 alkyl group wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfinyl C1-C6 alkyl group wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfonyl C1-C6 alkyl group wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 haloalkoxy C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a phenoxyimino C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a di(C1-C6 alkoxy)C1-C6 alkyl group;
a (R31R32N—C═O)C1-C6 alkyl group;
a C1-C6 alkoxycarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyloxy C1-C6 alkyl group;
a C1-C6 alkylidene aminooxy C1-C6 alkyl group;
a formyl C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C2-C6 alkylidene amino group;
a di(C1-C10alkyl)amino C1-C6 alkylidene amino group;
a NR31R32 group;
a C1-C6 alkoxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C3-C6 cycloalkyloxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;
a C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
and a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
R2 is selected from the group consisting of a C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
and a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α,
Y and Z are selected from the group consisting of an oxygen atom and a sulfur atom,
A is selected from the group consisting of formula A-1 and A-3,
R4 is selected from the group consisting of a hydroxyl group;
O−M+ wherein M+ is an alkali metal cation or an ammonium cation;
an amino group;
a halogen atom;
a cyano group;
an isothiocyanate group;
an isocyanate group;
a hydroxycarbonyloxy group;
a C1-C6 alkoxycarbonyloxy group;
a benzyloxycarbonyloxy group which may be substituted with a substituent group selected from substituent group α;
a C1-C6 alkoxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C3-C6 cycloalkyloxy group;
a cyanomethylene oxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 alkylcarbonyloxy group;
a C1-C6 haloalkylcarbonyloxy group;
a C2-C6 alkenylcarbonyloxy group;
a C2-C6 haloalkenylcarbonyloxy group;
a C2-C6 alkynylcarbonyloxy group;
a C2-C6 haloalkynylcarbonyloxy group;
a C1-C6 alkoxycarbonyl C1-C6 alkoxy group;
a phenyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a benzyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a phenylcarbonyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a benzylcarbonyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a phenylcarbonyl C1-C6 alkyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C10 alkylsulfonlyoxy group;
a C1-C6 haloalkylsulfonlyoxy group;
a phenylsulfonyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a benzylsulfonyloxy group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C10 alkylthio group;
a C1-C10 alkylsulfinyl group;
a C1-C10 alkylsulfonyl group;
a C1-C6 haloalkylthio group;
a C1-C6 haloalkylsulfinyl group;
a C1-C6 haloalkylsulfonyl group;
a C2-C6 alkenylthio group;
a C2-C6 alkenylsulfinyl group;
a C2-C6 alkenylsulfonyl group;
a C2-C6 alkynylthio group;
a C2-C6 alkynylsulfinyl group;
a C2-C6 alkynylsulfonyl group;
a phenylthio group which may be substituted with one or more substituents selected from the substituent group α;
a benzylthio group which may be substituted with one or more substituents selected from the substituent group α;
a phenylsulfinyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzylsulfinyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C10 alkylamino group;
a di(C1-C10 alkyl)amino group;
a C1-C6 alkoxycarbonylamino group;
a C1-C6 alkoxy group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α,
A1 is X1 or X2:
A2 is selected from the group consisting of X3, X4, X5, X6 and X7:
A3 is X8 or X9:
n is 0, 1, or 2,
R5, R6, R8, R9, R35 and R36 each independently is a hydrogen atom or a C1-C6 alkyl group, R5 and R8 may be joined together to form a C2-C5 alkylene chain or a C2-C5 alkenylene chain, and may form a ring together with adjacent carbon atoms, and R5 and R35 may be joined together to form a C1-C5 alkylene chain to form a ring with adjacent carbon atoms,
R7, R33, and R34 each independently is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, or a C1-C6 alkoxy group,
R20 is selected from the group consisting of a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, and a C3-C6 cycloalkyl C1-C6 alkyl group,
R21 is selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group, and a halogen atom,
R31 and R32 each independently is selected from the group consisting of a hydrogen atom;
a C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylcarbonyl group;
a C1-C10 alkylthio carbonyl group;
a C1-C6 alkoxycarbonyl group;
a C1-C6 haloalkyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl group;
a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
and a C1-C6 alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, herein, R31 and R32 may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom,
wherein substituent group α is selected from the group consisting of:
a halogen atom;
a hydroxyl group;
a C1-C6 alkyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
a C1-C6 alkoxy group;
a C3-C6 cycloalkyloxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C1-C6 alkylcarbonyloxy group;
a C1-C6 haloalkoxy group;
a C1-C6 alkylthio group;
a C1-C6 alkylsulfinyl group;
a C1-C6 alkylsulfonyl group;
a C1-C6 haloalkylthio group;
a C1-C6 haloalkylsulfinyl group;
a C1-C6 haloalkylsulfonyl group;
an amino group;
a C1-C6 alkylcarbonylamino group;
a mono(C1-C6 alkyl)amino group;
a di(C1-C6 alkyl)amino group;
a hydroxy C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkoxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy C1-C6 alkoxy group;
a cyano C1-C6 alkoxy group;
a C1-C6 acyl group;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a carboxyl group;
a C1-C6 alkoxycarbonyl group;
a carbamoyl group;
a mono(C1-C6 alkyl)aminocarbonyl group;
a di(C1-C6 alkyl)aminocarbonyl group;
a nitro group;
a cyano group;
a phenyl group wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
and a C3-C6 alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group;
and
wherein substituent group β is selected from the group consisting of:
a halogen atom, a nitro group, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group.

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6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

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6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

Life of this patent

Abstract

Claims15