Novel herbicides

Abstract

Compounds of formula I wherein the substituents are defined as in claim 1 , as well as the agronomically acceptable salts, isomers and enantiomers of these compounds, as well as the agronomically acceptable salts/N-oxides/isomers/enantiomers of these compounds, are eminently suitable for use as herbicides.

1 . A compound of formula I  
     
       
         
         
             
             
         
       
     
     wherein 
 X is L 1 -Y 1 -R 4 , L 2 -Y 2 -L 3 -Y 3 -R 5  or L 4 -Y 4 -L 5 -Y 5 -L 6 -Y 6 -R 6 ;  
 L 1  ,L 2 , L 3 , L 4 , L 5 , L 6 , independently of one another, signify C 1 -C 6 -alkylene, which may be substituted by C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl; or C 3 -C 6 -alkenylene, which may be substituted by C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl; or C 3 -C 6 -alkynylene, which may be substituted by C 1 -C 4 -alkyl, halogen, C 1 -C 4 -alkoxy, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl;  
 Y 1 , Y 3 , Y 6 , independently of one another, signify oxygen, sulphur, SO, SO 2 , NR 7 , OC(O), NR 8 SO 2  or OSO 2 ;  
 Y 2 , Y 4 , Y 5 , independently of one another, signify oxygen, sulphur, SO, SO 2 , NR 9 , OC(O) or NR 10 SO 2 ;  
 R 7 , R 8 , R 9  and R 10 , independently of one another, signify hydrogen or C 1 -C 6 -alkyl;  
 R 1  and R 2 , independently of one another, signify halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -dialkylaminosulphonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 4 -alkylsulphonylamino, C 1 -C 6 -halogenalkoxy, OSO 2 -C 1 -C 4 -alkyl, C 1 -C 6 -halogenalkylthio, C 1 -C 6 -halogenalkylsulphinyl, C 1 -C 6 -halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl;  
 R 3  signifies hydrogen, C 1 -C 4 -alkyl or halogen;  
 R 4 , R 5  and R 6 , independently of one another, signify hydrogen, C 1 -C 6 -alkyl, which may be substituted by the group A 1 ; C 3 -C 7 -cycloalkyl, which may be substituted by the group A 2 ; C 3 -C 7 -cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NR 11 ; C 2 -C 6 -alkenyl, which may be substituted by the group A 3 ; C 3 -C 6 -alkynyl, which may be substituted by the group A 4 ; C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NR 12 ; benzyl or phenyl which may in turn be substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, cyano, nitro, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -dialkylamino, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -dialkylaminosulphonyl or NR 13 -CO-R 14 ;  
 R 11  and R 12 , independently of one another, signify hydrogen or C 1 -C 4 -alkyl;  
 R 13  and R 14 , independently of one another, signify hydrogen or C 1 -C 4 -Alkyl; A 1 , A 2 , A 3 , A4, independently of one another, are hydroxy, formyl, COOH, C 1 -C 6 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, OS0 2 -C 1 -C 4 -alkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -dialkylaminocarbonyl, nitro, halogen, cyano, C 1 -C 4 -alkoxyhalogen, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or phenyl, whereby the phenyl group may in turn be substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, cyano, nitro, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -dialkylaminosulphonyl or NR 15 -CO-R 16 ;  
 R 15  and R 16 , independently of one another, signify hydrogen or C 1 -C 4 -alkyl; Q is the group Q 2    
                     
 wherein  
 R 23  signifies hydroxy, halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxy-carbonyloxy, C 1 -C 6 -dialkylamino, COOH, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphonyl, C 1 -C 6 -alkenylthio, C 1 -C 6 -alkenylsulphinyl, C 1 -C 6 -alkenylsulphonyl, OSO 2 -C 1 -C 6 -alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO 2 -phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, halogen, nitro, COOH or cyano; R 24  and R 25 , independently of one another, signify hydrogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkylaminosulphonyl, C 1 -C 4 -halogenalkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkyl-S(0) 2 O, C 1 -C 4 -halogenalkylthio, C 1 -C 4 -halogenalkylsulphinyl, C 1 -C 4 -halogenalkylsulphonyl, C 1 -C 4 -halogenalkyl-S(O) 2 O, C 1 -C 4 -alkyl-S(0) 2 NH, C 1 -C 4 -alkyl-S(O) 2 N(C 1 -C 4 -alkyl), halogen, nitro, COOH or cyano; or R 24  and R 25  together form a C 2 -C 6 -alkylene bridge, R 26  signifies hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl or phenyl, which may in turn be substituted by C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkyl-S(O) 2 O, C 1 -C 4 -halogen-alkylthio, C 1 -C 4 -halogenalkylsulphinyl, C 1 -C 4 -halogenalkylsulphonyl, C 1 -C 4 -halogenalkyl-S(O) 2 O, C 1 -C 4 -alkyl-S(O) 2 NH, C 1 -C 4 -alkyl-S(O) 2 N(C 1 -C 4 -alkyl), halogen, nitro, COOH or cyano;  
 or Q is the group Q 3    
                     
 wherein  
 R 27  signifies hydroxy, halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxy-carbonyloxy, C 1 -C 6 -dialkylamino, COOH, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl-sulphinyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphonyl, C 1 -C 6 -alkenylthio, C 1 -C 6 -alkenyl-sulphinyl, C 1 -C 6 -alkenylsulphonyl, OSO 2 -C 1 -C 6 -alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO 2 -phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, halogen, nitro, COOH or cyano;  
 R 28 , R 29  and R 40 , independently of one another, signify hydrogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkylaminosulphonyl, C 1 -C 4 -halogenalkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkyl-S(O) 2 O, C 1 -C 4 -halogenalkylthio, C 1 -C 4 -halogenalkylsulphinyl, C 1 -C 4 -halogenalkylsulphonyl, C 1 -C 4 -halogen-alkyl-S(O) 2 O, C 1 -C 4 -alkyl-S(O) 2 NH, C 1 -C 4 -alkyl-S(O) 2 N(C 1 -C 4 -alkyl), halogen, nitro, COOH or cyano; or R 28  and R 29  together form a C 2 -C 6 -alkylene bridge,  
 R 30  signifies C 1 -C 6 -alkyl, which may be substituted by a group A 5 ; C 2 -C 6 -alkenyl, which may be substituted by a group A 6 ; C 2 -C 6 -alkynyl, which may be substituted by a group A 7 ;  
 A 5 , A 6  and A 7 , independently of one another, are hydroxy, formyl, COOH, C 1 -C 6 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, OS0 2 -C 1 -C 4 -alkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -dialkylaminocarbonyl, nitro, halogen, cyano, C 1 -C 4 -alkoxyhalogen, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or phenyl, whereby the phenyl is in turn substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkyl, cyano, nitro, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkylsulphonyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -dialkylaminosulphonyl or NR 31 -CO-R 32 ;  
 R 31 , R 32 , independently of one another, signify hydrogen or C 1 -C 4 -alkyl; or Q is the group Q 4    
                     
 wherein  
 R 33  signifies hydroxy, halogen, Cl-C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxy-carbonyloxy, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphonyl, C 1 -C 6 -alkenylthio, C 1 -C 6 -alkenylsulphinyl, C 1 -C 6 -alkenylsulphonyl, OSO 2 -C 1 -C 6 -alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenyl-sulphonyl or OSO 2 -phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, halogen, nitro, COOH or cyano;  
 W is sulphur, SO, SO 2 , NR 38  or C═O;  
 R 38  signifies hydrogen or C 1 -C 6 -alkyl;  
 R 34 , R 35 , R 36  and R 37 , independently of one another, signify hydrogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkylaminosulphonyl, C 1 -C 4 -halogenalkyl, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, amino, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkyl-S(O) 2 O, C 1 -C 4 -halogenalkylthio, C 1 -C 4 -halogenalkylsulphinyl, C 1 -C 4 -halogenalkylsulphonyl, C 1 -C 4 -halogenalkyl-S(0) 2 O, C 1 -C 4 -alkyl-S(O) 2 NH, C 1 -C 4 -alkyl-S(O) 2 N(C 1 -C 4 -alkyl), halogen, nitro, COOH or cyano; or R 34  and R 35  together form a C 2 -C 6 -alkylene bridge, as well as agronomically acceptable salts, isomers and enantiomers of these compounds.  
 
   
   
       2 . A compound according to  claim 1 , whereby 
 R 1  and R 2 , independently of one another, signify halogen, cyano, nitro, amino, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 6 -dialkylaminosulphonyl, C 1 -C 6 -alkylaminosulphonyl, C 1 -C 6 -halogenalkoxy, OSO 2 -C 1 -C 4 -alkyl, C 1 -C 6 -halogenalkylthio, C 1 -C 6 -halogen-alkylsulphinyl, C 1 -C 6 -halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and    R 33  signifies hydroxy, halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxy-carbonyloxy, C 1 -C 6 -dialkylamino, COOH, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphinyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkylsulphonyl, C 1 -C 6 -alkenylthio, C 1 -C 6 -alkenylsulphinyl, C 1 -C 6 -alkenylsulphonyl, OSO 2 -C 1 -C 6 -alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO 2 -phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C 1 -C 4 -alkyl, C 1 -C 4 -halogenalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, halogen, nitro, COOH or cyano.    
   
   
       3 . Compounds according to  claim 1 , whereby Q is Q 1  or Q 2 .  
   
   
       4 . A compound according to  claim 1 , whereby X is L 1 -Y 1 -R 4 .  
   
   
       5 . A compound according to  claim 4 , whereby L 1  signifies methylene.  
   
   
       6 . A compound according to  claim 1 , whereby R 2  signifies C 1 -C 6 -alkylsulphonyl.  
   
   
       7 . A herbicidal and plant growth inhibiting composition, which comprises a herbicidally effective amount of the compound of formula I according to  claim 1  on an inert carrier.  
   
   
       8 . 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 according to  claim 1  or of a composition containing such a compound.  
   
   
       9 . A method of inhibiting undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I according to  claim 1  or of a composition containing such a compound.