Herbicidal Compounds

Abstract

The invention relates to pyrrolone compounds of the formula (I), wherein X, R 1 , R 2 , R 3 , R a , R b , R c and R d are as defined in the specification. Furthermore, the present invention relates to processes and intermediates for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control plant growth.

1 . A herbicidal compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         X is selected from S and O; 
         R a  is selected from hydrogen and halogen; 
         R b  is selected from hydrogen, halogen, C 1 -C 4  alkyl, C 2 -C 4  alkenyl C 1 -C 4  haloalkyl, C 1 -C 6  alkoxy, C 2 -C 4  alkenyloxy, C 2 -C 4  alkynyloxy, C 1 -C 4  alkoxy-C 1 -C 4  alkyl, C 1 -C 4  haloalkoxy, C 1 -C 3  alkoxy-C 1 -C 3  alkoxy, C 1 -C 4  alkylthio, C 1 -C 4  alkylsulfinyl, C 1 -C 4  alkylsulfonyl, a group R 5 R 6 N—, a group R 5 C(O)N(R 6 )—, a group R 5 S(O 2 )N(R 6 )—, a group R 5 R 6 NSO 2 —, a group R 5 R 6 NC(O)—, aryl optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and C 1 -C 3  haloalkoxy, aryloxy optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and C 1 -C 3  haloalkoxy and heteroaryl optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and C 1 -C 3  haloalkoxy; 
         R c  is selected from hydrogen, halogen, C 1 -C 8  alkyl, C 1 -C 6  haloalkyl, C 2 -C 8  alkenyl, C 1 -C 6  cyanoalkyl, C 1 -C 6  alkoxy, C 1 -C 4  alkoxy-C 1 -C 4  alkyl, C 1 -C 6  hydroxyalkyl, C 2 -C 6  alkenyloxy C 1 -C 6  alkyl and C 3 -C 6  cycloalkyl optionally substituted by from 1 to 3 groups independently selected from cyano, C 1 -C 3  alkyl and C 1 -C 3  alkoxy; 
         R d  is selected from hydrogen, halogen, cyano, C 1 -C 6  alkyl and C 1 -C 6  haloalkyl; 
         R 1  is selected from hydrogen, hydroxyl, C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 1 -C 4  cyanoalkyl, C 3 -C 6  cycloalkyl, C 1 -C 4  alkoxy, C 1 -C 4  alkoxy-C 1 -C 4  alkyl and C 1 -C 4  haloalkyl and R 2  is selected from hydrogen, hydroxyl, C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 1 -C 4  alkoxy, C 2 -C 4  alkenyloxy, C 2 -C 4  alkynyloxy, C 1 -C 4  alkoxy-C 1 -C 4  alkyl, C 1 -C 4  alkoxy-C 1 -C 4  alkoxy, C 1 -C 4  hydroxyalkyl, C 1 -C 4  haloalkyl, C 1 -C 3  haloalkoxy and C 1 -C 4  cyanoalkyl, with the proviso that when R 1  is methyl, R 2  is not H; 
         or R 1  and R 2  together with the nitrogen and carbon atoms to which they are attached form a 3-7 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from hydroxyl, ═O, C 1 -C 6  alkyl and C 1 -C 6  haloalkyl. 
         R 3  is selected from halogen, hydroxyl, —NR 14 R 15 , or any one of the following groups 
       
       
         
           
           
               
               
           
         
         R 5  and R 6  are independently selected from hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 1 -C 6  cyanoalkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy and C 1 -C 6  alkoxy-C 1 -C 6  alkyl, or R 5  and R 6  together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen and C 1 -C 6  alkyl; 
         R 7  and R 8  are independently selected from hydrogen, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, a C 3 -C 6  cycloalkyl group optionally substituted with 1 to 3 groups independently selected from C 1 -C 3  alkyl, C 2 -C 4  alkenyl, C 1 -C 3  haloalkyl and C 2 -C 4  haloalkenyl, a C 5 -C 10  heterocyclyl group which can be mono- or bicyclic comprising from 1 to 4 heteroatoms independently selected from N, O and S and optionally substituted with 1 to 3 groups independently selected from halogen, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl and C 1 -C 3  alkoxy, a C 5 -C 10  heteroaryl group which can be mono- or bicyclic comprising from 1 to 4 heteroatoms independently selected from N, O and S and optionally substituted with 1 to 3 groups independently selected from halogen, C 1 -C 3  alkyl, C 1 -C 3  haloalkyl and C 1 -C 3  alkoxy, a C 6 -C 10  aryl group optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and C 1 -C 3  haloalkoxy, a C 6 -C 10  arylalkyl group optionally substituted with 1 to 3 groups independently selected from C 1 -C 4  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and the group —OC(O)—C 1 -C 4  alkyl, or R 7  and R 8  together with the atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen and C 1 -C 6  alkyl; 
         R 9  is selected from C 1 -C 6  alkyl and benzyl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and C 1 -C 3  haloalkoxy; 
         R 14  and R 15  are independently selected from hydrogen, C 1 -C 20  alkyl, C 1 -C 20  haloalkyl, C 1 -C 20  alkoxy, C 1 -C 20  alkoxy-C 1 -C 20  alkyl, C 2 -C 20  alkenyl, C 2 -C 20  alkynyl and benzyl, or R 14  and R 15  together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen and C 1 -C 6  alkyl; 
         or an N-oxide or salt form thereof. 
       
     
     
         2 . The compound of  claim 1 , wherein X is O. 
     
     
         3 . The compound of claim, wherein R a  is hydrogen. 
     
     
         4 . The compound of  claim 1 , wherein R d  is hydrogen. 
     
     
         5 . The compound of  claim 1 , wherein R 1  is selected from C 1 -C 4  alkyl, C 1 -C 4  alkoxy and C 1 -C 4  haloalkyl. 
     
     
         6 . (canceled) 
     
     
         7 . (canceled) 
     
     
         8 . The compound of  claim 1 , wherein R 2  is selected from C 1 -C 3  alkyl, C 1 -C 3  alkoxy and C 1 -C 3  alkoxy-C 1 -C 3  alkyl. 
     
     
         9 . (canceled) 
     
     
         10 . The compound of  claim 1 , wherein R 3  is selected from hydroxyl, halogen, C 1 -C 6  alkylcarbonyloxy, C 1 -C 6  alkoxycarbonyloxy and aryloxycarbonyloxy wherein the aryl group may be substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  haloalkyl and C 1 -C 3  haloalkoxy. 
     
     
         11 . (canceled) 
     
     
         12 . (canceled) 
     
     
         13 . The compound of  claim 1 , wherein R b  is selected from hydrogen, halogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, C 1 -C 3  alkoxy-C 1 -C 3  alkyl, heteroaryl substituted by halogen or methoxy and aryl substituted by halogen or methoxy. 
     
     
         14 . (canceled) 
     
     
         15 . (canceled) 
     
     
         16 . The compound of  claim 1 , wherein R c  is selected from C 1 -C 8  alkyl, C 1 -C 6  haloalkyl, C 2 -C 8  alkenyl, C 1 -C 6  cyanoalkyl and C 3 -C 6  cycloalkyl optionally substituted by from 1 to 3 groups independently selected from cyano and C 1 -C 3  alkyl. 
     
     
         17 . (canceled) 
     
     
         18 . (canceled) 
     
     
         19 . (canceled) 
     
     
         20 . (canceled) 
     
     
         21 . The compound of  claim 1  wherein R b  is selected from R 5 R 6 NC(O)— and R 5 C(O)N(R 6 )— and R c  is selected from hydrogen, halo, C 1 -C 4  alkyl and C 1 -C 4  haloalkyl. 
     
     
         22 . (canceled) 
     
     
         23 . The compound of  claim 1 , wherein R b  is selected from halo and C 1 -C 4  alkyl and R c  is C 1 -C 3  haloalkyl. 
     
     
         24 . (canceled) 
     
     
         25 . A herbicidal composition comprising a compound of formula I as defined in  claim 1  together with at least one agriculturally acceptable adjuvant or diluent. 
     
     
         26 . A composition according to  claim 25  which comprises a further herbicide in addition to the compound of formula I. 
     
     
         27 . A composition according to  claim 24  which comprises a safener. 
     
     
         28 . (canceled) 
     
     
         29 . A method of controlling weeds in crops of useful plants, comprising applying to said weeds or to the locus of said weeds, or to said useful plants or to the locus of said useful plants, a compound of formula I as defined in  claim 1 .