Triketone derivatives and herbicides

Abstract

The present invention relates to a novel triketone derivative having a specific structure and a herbicide containing the triketone derivative as an active ingredient. The herbicide is effective for controlling weeds which inhibit growth of crop plants, inter alia, for paddy weeds such as Sanwa millet and Scirups juncoides.

1 . A triketone derivative represented by formula [I-1]:  
       
         
           
           
               
               
           
         
       
       wherein R represents a methyl group; each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, an amino group, a cyano group, a hydroxy group, a mercapto group, —R 1 , —OR 1 , —SR 1 , —SO 2 R 1 , —NR 2 R 3 , or —NHCOR 1 , wherein R 1  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 R 2  and R 3  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 R 2  and R 3  may be bonded to each other to form a group having a cyclic structure; M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base; R 4  represents a hydrogen atom or a C1-C6 alkyl group; and m is an integer between 0 and 4 inclusive; provided that not all of X, Y, and R 4  simultaneously represent methyl groups.  
     
     
         2 . A triketone derivative represented by formula [I-2]:  
       
         
           
           
               
               
           
         
       
       wherein R, X, Y, M, and m have the same definitions as described in relation to formula [I-1].  
     
     
         3 . A triketone derivative represented by formula [I-3]:  
       
         
           
           
               
               
           
         
       
       wherein R, X, M, R 4 , and m have the same definitions as described in relation to formula [I-1].  
     
     
         4 . A triketone derivative represented by formula [I-4]:  
       
         
           
           
               
               
           
         
       
       wherein R represents a methyl group; each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, —R 1 , —OR 1 , —SR 1 , or —NR 2 R 3 , wherein R 1  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 R 2  and R 3  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 R 2  and R 3  may be bonded to each other to form a group having a cyclic structure; Z represents —OR 1 , —SO p R 1 , —A(CH 2 ) n QR 1 , —NR 2 R 3 , —N(OR 1 )R 2 , —O(C═O)R 1 , —O(C═O)OR 1 , —O(C═O)SR 1 , —O(C═O)NR 2 R 3 , or —O(C═S)NR 2 R 3  (wherein R 1 , R 2 , and R 3  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.  
     
     
         5 . A triketone derivative according to  claim 4 , wherein Z represents an —OM group (wherein M represents a hydrogen atom, an alkali metal, an alkaline earth metal, or an organic base).  
     
     
         6 . A triketone derivative according to any one of claims  1 ,  2 ,  4 , and  5 , wherein Y represents a hydrogen atom, a C1-C6 alkyl group, or a halogen atom.  
     
     
         7 . A triketone derivative according to any one of claims  1 ,  2 ,  4 , and  5 , wherein Y represents a hydrogen atom or a methyl group.  
     
     
         8 . A triketone derivative according to any one of claims  2 ,  4 , and  5 , wherein Y represents a hydrogen atom.  
     
     
         9 . A triketone derivative according to any one of claims  1  through  8 , wherein X represents —R 1 , —OR 1 , or —SR 1 .  
     
     
         10 . A triketone derivative according to  claim 1  or  9 , wherein X represents a halogen atom or a methyl group.  
     
     
         11 . A triketone derivative according to any one of claims  1  through  10 , wherein M represents a hydrogen atom.  
     
     
         12 . A herbicide containing a triketone derivative as recited in any one of claims  1  through  11  as an active ingredient.  
     
     
         13 . A herbicide for use in cultivation of a paddy rice plant, which herbicide contains a triketone derivative as recited in any one of claims  1  through  11  as an active ingredient.  
     
     
         14 . A triketone derivative represented by formula [II-1]:  
       
         
           
           
               
               
           
         
       
       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, —R 1 , —OR 1 , —SR 1 , —SO 2 R 1 , —NR 2 R 3 , or —NHCOR 1  (wherein R 1  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 R 2  and R 3  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 R 2  and R 3  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;  
 Z 1  represents a halogen atom, —OR 1 , —SO p R 1 , —A(CH 2 ) n QR 1 , —NR 2 R 3 , —N (OR 1 ) R 2 , —O(C═O)R 1 , —O(C═O)OR 1 , —O(C═O)SR 1 , —O(C═O)NR 2 R 3 , or —O(C═S)NR 2 R 3  (wherein R 1 , R 2 , and R 3  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.  
 
     
     
         15 . A triketone derivative according to  claim 14 , which is represented by formula [II-2] or [II-3]:  
       
         
           
           
               
               
           
         
       
       wherein R, X, G, Z 1 , m, and q have the same definitions as described in relation to formula [II-1].  
     
     
         16 . A triketone derivative according to  claim 14  or  15 , which is represented by any one of formulas [II-4] to [II-9]:  
       
         
           
           
               
               
           
         
       
       wherein R, X, G, Z 1 , m, and q have the same definitions as described in relation to formula [II-1], each of G 1  to G 4  represents an optionally substituted atom that constitutes G in formula [II-1], and i is 0, 1, or 2.  
     
     
         17 . A triketone derivative according to any one of claims  14  through  16 , wherein X represents a halogen atom, —R 1 , —OR 1 , or —SR 1 .  
     
     
         18 . A triketone derivative according to  claim 16  or  17 , wherein each of G 1  to G 4  represents a ring-constituting atom having one or more substituents selected from the substituent group consisting of an unsubstituted or C1-C6 alkyl group, a C1-C6 alkoxy group, an oxo group, and a C1-C6 alkoxyimino group.  
     
     
         19 . A triketone derivative according to any one of  claims 14  to  18 , wherein Z 1  is selected from among a halogen atom, —OR 1 , —SO p R 1 , —A(CH 2 ) n QR 1 , and —N(OR 1 )R 2 .  
     
     
         20 . A triketone derivative represented by formula [II-10]:  
       
         
           
           
               
               
           
         
       
       wherein R represents a methyl group; each of X and Y represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, —R 1 , —OR 1 , —SR 1 , or —NR 2 R 3  (wherein R 1  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 R 2  and R 3  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 R 2  and R 3  may be bonded to each other to form a group having a cyclic structure); Z represents —OR 1 , —SO p R 1 , —A(CH 2 ) n QR 1 , —NR 2 R 3 , —N(OR 1 )R 2 , O(C═O)R 1 , —O(C═O)OR 1 , —O(C═O)SR 1 , —O(C═O)NR 2 R 3 , or —O(C═S)NR 2 R 3  (wherein R 1 , R 2 , and R 3  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.  
     
     
         21 . A triketone derivative according to  claim 20 , wherein Y represents a hydrogen atom or a methyl group.  
     
     
         22 . A triketone derivative according to  claim 20 , wherein Y represents a hydrogen atom.  
     
     
         23 . A triketone derivative according to any one of claims  20  through  22 , wherein Z represents a halogen atom, —OR 1 , —SO p R 1 , —A(CH 2 ) n QR 1 , or —N(OR 1 )R 2 .  
     
     
         24 . A triketone derivative according to any one of claims  14  through  23 , wherein X represents a halogen atom or a methyl group.  
     
     
         25 . A herbicide containing a triketone derivative as recited in any one of claims  14  through  24  as an active ingredient.  
     
     
         26 . A herbicide for use in cultivation of a paddy rice plant, which herbicide contains a triketone derivative as recited in any one of claims  14  through  24  as an active ingredient.