Triketone derivatives and herbicides

A triketone derivative represented by formula [I-4]:

• 136
• wherein R represents a methyl group;
• each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, —R1, —OR1, —SR1, or —NR2R3, wherein R1 represents a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted;
• each of R2 and R3 represents a hydrogen atom, a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, or R2 and R3 may be bonded to each other to form a group having a cyclic structure;
• Z represents —OR1, —SOpR1, —A(CH2)nQR1, —NR2R3, —N(OR1)R2, —O(C═O)R1, —O(C═O)OR1, —O(C═O)SR1, —O(C═O)NR2R3, or —O(C═S)NR2R3 (wherein R1, R2, and R3 have the same definitions as described in relation to X and Y, each of A and Q represents an oxygen atom or a sulfur atom, p is 0, 1, or 2, n is 1 or 2), —OM (wherein M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base), or a halogen atom;
• and m is an integer between 0 and 4 inclusive.

A triketone derivative represented by formula [II-1]:

• 137
• wherein R represents a methyl group;
• X represents a hydrogen atom, a halogen atom, a nitro group, an amino group, a cyano group, a hydroxy group, a mercapto group, —R1, —OR1, —SR1, —SO2R1, —NR2R3, or —NHCOR1 (wherein R1 represents a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted;
• each of R2 and R3 represents a hydrogen atom, a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, or R2 and R3 may be bonded to each other to form a group having a cyclic structure);
• G contains 3 to 5 ring-constituting atoms which form a 5- to 7-membered saturated or unsaturated condensed ring including two carbon atoms of the benzene ring adjacent to G, wherein two or less ring-constituting atoms are selected from among nitrogen, oxygen, and sulfur, and the ring-constituting atoms may have one or more substituents selected from among a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a hydroxy group, a mercapto group, an oxo group, a thioxo group, a hydroxyimino group, a C1-C6 alkoxyimino group, a hydrazono group, a C1-C6 monoalkylhydrazono group, and a C1-C6 dialkylhydrazono group, and a carbon atom or the adjacent carbon atom of the ring-constituting atom may have a substituent selected from among an ethylenedioxy group, an ethylenedithio group, a propylenedioxy group, and a propylenedithio group, with these substituents optionally being substituted with a halogen atom or a C1-C6 alkyl group;
• Z1 represents a halogen atom, —OR1, —SOpR1, —A(CH2)nQR1, —NR2R3, —N (OR1) R2, —O(C═O)R1, —O(C═O)OR1, —O(C═O)SR1, —O(C═O)NR2R3, or —O(C═S)NR2R3 (wherein R1, R2, and R3 have the same definitions as described in relation to X, each of A and Q represents an oxygen atom or a sulfur atom, p is 0, 1, or 2, n is 1 to 3), or a halogen atom;
• m is an integer between 0 and 4 inclusive;
• and q is 1 or 2.

A triketone derivative represented by formula [II-10]:

• 140
• wherein R represents a methyl group;
• each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, —R1, —OR1, —SR1, or —NR2R3 (wherein R1 represents a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, each of R2 and R3 represents a hydrogen atom, a C1-C6 alkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a C1-C6 haloalkyl group which may have a branched structure, a cyclic structure, or an unsaturated bond, a phenyl group which may be substituted, or a benzyl group which may be substituted, or R2 and R3 may be bonded to each other to form a group having a cyclic structure);
• Z represents —OR1, —SOpR1, —A(CH2)nQR1, —NR2R3, —N(OR1)R2, O(C═O)R1, —O(C═O)OR1, —O(C═O)SR1, —O(C═O)NR2R3, or —O(C═S)NR2R3 (wherein R1, R2, and R3 have the same definitions as described in relation to X and Y, each of A and Q represents an oxygen atom or a sulfur atom, p is 0, 1, or 2, n is 1 or 2), —OM (wherein M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base), or a halogen atom;
• and m is an integer between 0 and 4 inclusive.