Herbicidal phenylethers

Abstract

The present invention relates to phenylethers of formula (I) or their agriculturally acceptable salts or derivatives, wherein the variables are defined according to the description, processes and intermediates for preparing the phenylethers of formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one phenylether of formula (I) to act on plants, their seed and/or their habitat.

1 . Phenylethers of formula (I) 
       
         
           
           
               
               
           
         
         wherein the variables have the following meanings: 
         R 1  H or halogen; 
         R 2  H, halogen, CN, NO 2 , NH 2 , CF 3  or C(═S)NH 2 ; 
         R 3  H, halogen, CN, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, (C 1 -C 3 -alkyl)amino, di(C 1 -C 3 -alkyl)amino, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 3 -alkoxycarbonyl; 
         R 4  H, halogen, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy; 
         R 5  OR 6 , SR 6 , NR 7 R 8 , NR 6 OR 6 , NR 6 S(O) 2 R 7  or NR 6 S(O) 2 NR 7 R 8 , wherein
 R 6  is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -cyanoalkyl, alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkoxy)C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -haloalkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulfonyl-C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxycarbonyl-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl-C 1 -C 6 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-C 1 -C 6 -alkyl, amino, (C 1 -C 6 -alkyl)amino, di(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkylcarbonyl)amino, (C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, aminocarbonyl-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl,
 —N═CR 9 R 10 , wherein R 9  and R 10  independently of one another are H, C 1 -C 4 -alkyl or phenyl; 
 C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -heterocyclyl-C 1 -C 6 -alkyl, phenyl, phenyl-C 1 -C 1 -c 4 -alkyl or a 5-or 6 membered heteroaryl,
 wherein each cycloalkyl, heterocyclyl, phenyl or heteroaryl ring can be substituted by one to four substituents selected from R 13  or a 3- to 7-membered carbocyclus, 
  which carbocyclus optionally has in addition to carbon atoms one or two ring members selected from the group consisting of —N(R 9 )—, —N═N—, —C(═O)—, —O—and —S—, and 
  which carbocyclus is optionally substituted with one to four substituents selected from R 11 ; 
   wherein R 11  is halogen, NO 2 , CN, C 1 -C 4 -halo-alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxycarbonyl; 
 
 
 R 7 , R 8  independently of one another are R 6 , or together form a 3- to 7-membered carbocyclus,
 which carbocyclus optionally has in addition to carbon atoms one or two ring members selected from the group consisting of —N(R 9 )—, —N═N—, —C(═O)—, —O—and —S—, and 
 which carbocyclus is optionally substituted with one to four substituents selected from R 11 ; 
 
 
         n 1 to 3; 
         Q O, S, SO, SO 2 , NH or (C 1 -C 3 -alkyl)N; 
         W O or S; 
         X O or S; 
         Y is a heterocycle selected from the group consisting of Y 1  to Y 73    
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein 
         A 1 , A 2 , A 3  are oxygen or sulfur; 
         A 4  is oxygen, sulphur, SO or SO 2 ; 
         R 12 , R 13 , R 14 , R 15 , R 16 , R 17  and R 18  
 are hydrogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsolfonyl, C 1 -C 6 -alkoxysulfonyl, C 1 -C 6 -alkylsulfonyloxy, amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino; or 
 
         R 12  and R 13  together with the atoms to which they are attached, form a three- to six-membered cycle, which is saturated, partial unsaturated or aromatic, which may comprise apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, and which for its part may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; 
         R19, R 20 , R 21 , R 22 , R 23 , R 24  are hydrogen, cyano, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 alkyl-sulfonyl, phenyl-C 1 -C 6 -alkyl, amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino; or 
         R 21  and R 22  together with the atoms to which they are attached, form a three- to six-membered cycle, which is saturated, partial unsaturated or aromatic, which may comprise apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, and which for its part may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; 
         R 25  is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkoxy, amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino; 
         R 26  and R 27  
 are hydrogen, halogen or C 1 -C 6 -alkyl; 
 
         R 28 , R 29  and R 30  
 are hydrogen, halogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl or C 3 -C 6 -alkynyloxy; and 
 
         R 31  is hydrogen, NH 2 , C 1 -C 6 -alkyl or C 3 -C 6 -alkynyl; 
         R 32 , R 33  and R 34  
 are hydrogen, amino, nitro, cyano, carboxy, carbamoyl, thiocarmbamoyl, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cyclo-alkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -halo-alkylthio, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenylthio, C 3 -C 6 -alkynylthio, di(C 1 -C 6 -alkyl)amino di(C 1 -C 6  or C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl; 
 
         R 35  and R 36  
 are hydrogen, cyano, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxycarbonyl, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 3 -C 7 -cycloalkyl-C 1 -C 3 -alkyl, phenyl or phenyl-C 1 -C 6 -alkyl; 
 
         R 37  halogen or C 1 -C 6 -alkyl; 
         Z phenyl, pyridyl, pyridazinyl, pyrimidinyl or pyrazinyl,
 each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy; 
 
         including their agriculturally acceptable salts or derivatives, provided the compounds of formula (I) have a carboxyl group. 
       
     
     
         2 . Phenylethers of formula (I) according to  claim 1  wherein R 1  is H or F, and R 2  is F, Cl or CN. 
     
     
         3 . Phenylethers of formula (I) according to  claim 1 , wherein R 3  is H, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy, and R 4  is H. 
     
     
         4 . Phenylethers of formula (I) according to  claim 1 , wherein R 5  is OR 6, NR 6 S(O) 2 R 7  or NR 6 S(O) 2 NR 7 R 8 , wherein
 R 6  is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkoxy)C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl; and   R 7 , R 8  are C 1 -C 6 -alkyl.   
     
     
         5 . Phenylethers of formula (I) according to  claim 1  to wherein n is 1. 
     
     
         6 . Phenylethers of formula (I) according to  claim 1  wherein Q, W and X are O. 
     
     
         7 . Phenylethers of formula (I) according to  claim 1 , wherein Y is selected from the group consisting of Y 2 , Y 13 , Y 20 , Y 31 , Y 37 , Y 38 , Y 39 , Y 42 , Y 48 , Y 55 , Y 65 , Y 66 , Y 67  or Y 68 . 
     
     
         8 . Phenylethers of formula (I) according to  claim 1 , wherein Z is phenyl or pyridyl, each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and C 1 -C 6 -haloalkoxy. 
     
     
         9 . A herbicidal composition comprising an herbicidally active amount of at least one phenylether of formula (I) as claimed in  claim 1  and at least one inert liquid and/or solid carrier. 
     
     
         10 . A process for the preparation of herbicidal active compositions, which comprises mixing an herbicidally active amount of at least one phenylether of formula (I) as claimed in  claim 1  and at least one inert liquid and/or solid carrier. 
     
     
         11 . A method of controlling undesired vegetation, which comprises allowing an herbicidally active amount of at least one phenylether of formula (I) as claimed in  claim 1  to act on plants, their environment or on seed. 
     
     
         12 . The use of the phenylethers of formula (I) as claimed in  claim 1  as herbicides. 
     
     
         13 . The herbicidal composition according to  claim 9 , further comprising at least one surface-active substance. 
     
     
         14 . The process according to  claim 10 , wherein at least one surface-active substance is mixed with the herbicidally active amount of the least one phenylether of formula (I) and the at least one inert liquid and/or solid carrier.