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

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 said phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, a phenylthio C1-C6 alkyl group wherein said phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, a phenylsulfinyl C1-C6 alkyl group wherein said phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, a phenylsulfonyl C1-C6 alkyl group wherein said phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from 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 substituent group α, a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from substituent group α, a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from substituent group α, a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from 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 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-C10 alkyl)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 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 the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from 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 the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, 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 the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein said heterocyclic group optionally substituted with 1 to 5 identical or different substituents selected from substituent group α, and a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom being optionally oxidized to sulfoxide or sulfone;
• 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 the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group α;
• a phenyl group which may be substituted with one or more substituents selected from substituent group α, a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from substituent group α, a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from substituent group α, and a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from 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 A-1, A-2, A-3, A-4, and A-5, as depicted below;
• R4 is selected from the group consisting of a hydroxyl group, O−M+ wherein M+ represents 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 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 substituent group α, a benzylcarbonyloxy group which may be substituted with one or more substituents selected from substituent group α, a phenylcarbonyl C1-C6 alkyloxy group which may be substituted with one or more substituents selected from 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 substituent group α, a benzylsulfonyloxy group which may be substituted with one or more substituents selected from 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 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-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 the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from 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 heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, and 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 the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein the heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group α;
• A1 is selected from the group consisting of X1 and X2, as depicted by the following formulas
• A2 is selected from the group consisting of X3, X4, X5, X6, and X7, as depicted by the following formulas
• A3 is selected from the group consisting of X8 and X9, as depicted by the following formulas
• n is selected from the group consisting of 0, 1, and 2;
• R5, R6, R8, R9, R35 and R36 are each independently selected from the group consisting of a hydrogen atom and a C1-C6 alkyl group, wherein, 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 are each independently selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, and a C1-C6 alkoxy group;
• R14, R15, R16 and R17 are each independently selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a benzyl group which may be substituted with one or more substituents selected from the substituent group α;
• R18 is selected from the group consisting of a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyanomethyl group, and a benzyl 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;
• R23 is selected from the group consisting of a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, a C1-C10 alkylthio group, a C1-C10 alkylsulfinyl group, a C1-C10 alkylsulfonyl 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 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, and a benzylsulfonyl group which may be substituted with one or more substituents selected from substituent group α;
• R24 is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, and a C1-C6 alkoxycarbonylamino group;
• R25 is selected from the group consisting of a C1-C6 alkoxycarbonyl group, a cyano group, and a nitro group;
• R31 and R32 are each independently 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 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 substituent group α, a benzylsulfonyl group which may be substituted with one or more substituents selected from substituent group α, a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein said heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from 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 said heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group α, wherein R31 and R32 may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and 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 optionally substituted with 1 to 5 identical or different substituents selected from substituent group β, a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein said heterocyclic group may be substituted with 1 to 5 identical or different substituents selected from substituent group β, a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom wherein said heterocyclic oxy group may be substituted with 1 to 5 identical or different substituents selected from 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 the group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group;
• and
• “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.