Novel herbicides

Abstract

Compounds of formula 1 R 1 is hydrogen, fluorine, chlorine, bromine or methyl; R 2 is C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkoxy, nitro, amino or cyano; R 3 , R 15 to R 39 and X 6 to X 19 are as defined in claim 1, and the agrochemically acceptable salts and stereoisomers of these compounds of formula I are suitable for use as herbicides.

What is claimed is:  
     
         1 . Compounds of formula I  
       
         
           
           
               
               
           
         
         R 1  is hydrogen, fluorine, chlorine, bromine or methyl;  
         R 2  is C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, halogen, hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 halogenalkoxy, nitro, amino or cyano;  
         R 3  is cyano or R 4 C(O)—;  
         R 4  is hydrogen, fluorine, chlorine, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkinyl, C 3 -C 6 cycloalkyl, C 1 -C 8 halogenalkyl, cyano-C 1 -C 4 alkyl, C 2 -C 8 halogenalkenyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 3 -C 6 alkenyloxy-C 1 -C 4 alkyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, phenyl, phenyl substituted once to three times by halogen, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl, benzyl or benzyl substituted once to three times on the phenyl ring by halogen, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl; or  
         R 3  is R 5 X 1 C(O)—;  
         X 1  is oxygen, sulfur,  
         
           
             
             
                 
                 
             
           
         
         R 5  is hydrogen, C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkinyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 1 C 6 alkyl, C 1 -C 8 halogenalkyl, C 3 -C 8 halogenalkenyl, cyano-C 1 -C 4 alkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 3 -C 6 alkenyloxy-C 1 -C 4 alkyl, (oxiranyl)-CH 2 —oxetanyl-, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, phenyl, phenyl substituted once to three times by halogen, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl, benzyl or benzyl substituted once to three times on the phenyl ring by halogen, C 1 -C 4 alkyl or C 1 -C 4 -  
         
           
             
             
                 
                 
             
           
         
         R 8  is hydrogen, C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkinyl, C 3 -C 6 cycloalkyl, C 1 -C 8 halogenalkyl, C 3 -C 8 halogenalkenyl, cyano-C 1 -C 4 alkyl, C 1 - 4 alkoxy-C 1 -C 4 alkyl, C 3 -C 6 alkenyloxy-C 1 -C 4 alkyl, (oxiranyl)-CH 2 -, oxetanyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl, phenyl, phenyl substituted once to three times by halogen, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl, benzyl, benzyl substituted once to three times on the phenyl ring by halogen, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl, or phenyl-C 2 -C 6 alkyl;  
         R 6 , R 7 , R 9  and R 10  are independently of one another hydrogen, C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkinyl, C 1 -C 8 halogenalkyl or benzyl; or  
         R 3  is B 1 —C 1 -C 8 alkyl, B 1 —C 2 - 8 alkenyl, B 1 —C 2 -C 8 alkinyl, B 1 —C 1 -C 8 halogenalkyl, B 1 —C 2 -C 8 halogenalkenyl, B 1 —C 1 -C 4 alkoxy-C 1 -C 4 alkyl, B 1 —C 1 -C 4 alkylthio-C 1 -C 4 alkyl or B 1 —C 3 -C 6 cycloalkyl;  
         B 1  is hydrogen, cyano, hydroxy, C 1 -C 8 alkoxy, C 3 - 8 alkenyloxy, R 11 X 3 C(O)—, C 1 -C 4 alkylcarbonyl or C 1 -C 4 halogenalkylcarbonyl;  
         X 3  has the same meaning as X 2 ;  
         R 11  has the same meaning as R 8 ; or  
         R 3  is B 2 —C(R 12 )═CH—;  
         B 2  is nitro, cyano or R 13 X 4 C(O)—;  
         R 12  is cyano or R 14 X 5 C(O)—;  
         X 4  and X 5  have the same meaning as X 2 ; and  
         R 13  and R 14  have the same meaning as R 8 ;  
         
           
             
             
                 
                 
             
           
         
         R 15  is C 1 -C 3 alkyl, C 1 -C 3 halogenalkyl or amino;  
         R 16  is C 1 -C 3 halogenalkyl, C 1 -C 3 alkyl-S(O) n1  , C 1 -C 3 halogenalkyl-S(O) n1  or cyano; or  
         R 16  and R 15  together form a C 3 - or C 4 alkylene or C 3 - or C 4 alkenylene bridge which may be substituted by halogen, C 1 -C 3 halogenalkyl or cyano;  
         n, is 0, 1 or 2;  
         R 17  is hydrogen, C 1 -C 3 alkyl, halogen, C 1 -C 3 halogenalkyl or cyano; or  
         R 17  and R 16  together form a C 3 - or C 4 alkylene or C 3 -or C 4 alkenylene bridge which may be substituted by halogen, C 1 -C 3 halogenalkyl or cyano;  
         R 18  is hydrogen, C 1 -C 3 alkyl, halogen or cyano;  
         R 19  is C 1 -C 3 halogenalkyl; or  
         R 19  and R 18  together form a C 3 - or C 4 alkylene or C 3 -or C 4 alkenylene bridge which may be substituted by halogen, C 1 -C 3 halogenalkyl or cyano;  
         R 20  is hydrogen or C 1 -C 3 alkyl or halogen; or  
         R 20  and R 19  together form a C 3 - or C 4 alkylene or C 3 - or C 4 alkenylene bridge which may be substituted by halogen, C 1 -C 3 halogenalkyl or cyano;  
         R 21  is hydrogen, C 1 -C 3 alkyl, halogen, C 1 -C 3 halogenalkyl, R 40 O—, R 41 S(O) n2 , R 42 (R 43 )N, R 45 (R 46 )N—C(R 44 )═N—, hydroxy, nitro or N≡C—S—;  
         R 40  is C 1 -C 3 alkyl, C 1 -C 3 halogenalkyl, C 2 -C 4 alkenyl, C 3 - or C 4 alkinyl or C 1 -C 5 alkoxycarbonyl-C 1 -C 4 alkyl;  
         R 41  is C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl;  
         n 2  is 0, 1 or 2;  
         R 42  is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, C 3 -C 6 cycloalkyl, OHC— or C 1 -C 4 alkylcarbonyl;  
         R 43 , R 44 , and R 46  are independently of one another hydrogen or C 1 -C 4 alkyl;  
         R 45  is C 1 -C 4 alkyl;  
         R 22  is hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 halogenalkyl, C 2 -C 4 alkenyl, C 3 -C 5 halogenalkenyl,  
         C 3 - or C 4 alkinyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 halogenalkylcarbonyl, C 2 -C 4 alkenylcarbonyl, C 2 -C 4 halogenalkenylcarbonyl, C 2 -C 4 alkinylcarbonyl, C 2 -C 4 halogenalkinylcarbonyl, C 1 -C 4 alkylcarbamoyl, C 1 -C 4 alkylS(O) n3 , C 3 - or C 4 alkinylS(O) n3 , OHC—, nitro, amino, cyano or N≡C—S—;  
         n 3  is 0, 1 or 2;  
         R 23  and R 24  are independently of one another hydrogen, C 1 -C 4 alkyl, halogen, C 1 -C 4 halogen-alkyl or cyano;  
         R 25  and R 26  are independently of one another hydrogen, methyl, halogen, hydroxy or ═O;  
         R 27  and R 28  are independently of one another hydrogen, C 1 -C 4 alkyl or C 1 -C 4 halogenalkyl;  
         R 29  and R 30  are independently of one another hydrogen, C 1 -C 3 alkyl or halogen;  
         R 31  and R 32  are independently of one another hydrogen or C 1 -C 4 alkyl; or  
         R 31  and R 32  together form the group  
         
           
             
             
                 
                 
             
           
         
         R 47  and R 48  are independently of one another C 1 -C 4 alkyl; or  
         R 47  and R 48  together form a C 4  or C 5 alkylene bridge;  
         R 33  is hydrogen or C 1 -C 3 alkyl; or  
         R 33  together with R 32  forms a C 3 -C 5 alkylene bridge which may be broken by oxygen and/or substituted by halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 3 alkylcarbonyloxy, C 1 -C 3 alkylsulfonyloxy, hydroxy or ═O;  
         R 34 , R 35 , R 36  and R 37  are independently of one another hydrogen, C 1 -C 3 alkyl, C 3 - or C 4 alkenyl or C 3 -C 5 alkinyl; or  
         R 34  and R 35  on the one hand and R 36  and R 37  on the other each form a C 2 -C 5 alkylene or C 3 -C 5 alkenylene bridge together, which may be broken by oxygen, —C(O)—, sulfur, or —S(O) 2 —;  
         R 38  is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 halogenalkyl, C 3 - or C 4 alkenyl or C 3 - or C 4 alkinyl;  
         R 39  is hydrogen, C 1 -C 4 alkyl, C 1 -C 3 alkoxy-C 1 - or -C 2 alkyl, C 1 -C 4 halogenalkyl, C 3 - or or C 4 alkenyl, C 3 -C 4 halogenalkenyl or C 3 - or C 4 alkinyl; or  
         R 39  and R 38  together form a C 3 -C 5 alkylene bridge; and  
         X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18  and X 19  are independently of one another oxygen or sulfur,  
         and the agrochemically acceptable salts and stereoisomers of these compounds of formula I  
       
     
     
         2 . Compounds of formula I of  claim 1 , wherein R 2  is methyl, halogen, hydroxy, nitro, amino or cyano.  
     
     
         3 . A method for the preparation of compounds of formula I,  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , A and W are as defined in  claim 1 , comprising treating a compound of formula II  
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2  and W have the meanings indicated, and L 4  is a leaving group, either 
 a) in a suitable solvent, where appropriate in the presence of a base, a catalyst and a compound of formula V 
 R 5 —OH  (V), 
 wherein R 5  is hydrogen or C 1 -C 4 alkyl, under positive pressure with carbon monoxide, or  
 b) in a suitable solvent in the presence of a tertiary amine, a catalyst, and an olefin by means of the Heck reaction, or under said conditions by means of reaction with a Grignard reagent of formula Va 
 R 3 —Mg-halogenide  (Va), 
 wherein R 3  is B 1 —C 1 -C 8 alkyl, B 1 —C 2 -C 8 alkenyl, B 1 —C 2 -C 8 alkinyl, B 1 —C 1 -C 8 halogenalkenyl, B 1 —C 2 -C 8 halognealkenyl, B 1 —C 1 -C 4 alkoxy-C 1 -C 4 alkyl, B 1 —C 1 -C 4 alkylthio-C 1 -C 4 alkyl or B 1 —C 3 -C 6 cycloalkyl and B 1  has the meaning defined in  claim 1 , or in an inert solvent and in the presence of a catalyst with a tin compound of formula Vb 
 (R 3 ) 4 Sn  (Vb), 
 wherein R 3  has the meaning indicated, or  
 c) where applicable in an inert solvent at reaction temperatures of  20-300 ° C. subjecting said compound to a cyanidation reaction, or  
 d) first oxidizing said compound in a suitable solvent to form a compound of formula IV  
                     
 and treating this in an inert solvent with dimethylcarbamoyl chloride and a cyanidation reagent, and then where applicable further functionalizing the compound according to the definitions of A and R 3 .  
 
     
     
         4 . Compounds of formula II  
       
         
           
           
               
               
           
         
       
       wherein R 1  and R 2  are as defined in  claim 1 , W is a W 3 , W 4 , W 5 , W 6 , W 9  or W 10  group and L 4  is a leaving group.  
     
     
         5 . A herbicidal and plant growth inhibiting composition, which comprises a herbicidally effective amount of the compound of formula I on an inert carrier.  
     
     
         6 . A herbicidal and plant growth inhibiting composition of  claim 5  comprising as an additional component a further co-herbicide.  
     
     
         7 . A method of controlling undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.  
     
     
         8 . Use of a composition according to  claim 5  for controlling undesirable plant growth.