Phenyl-substituted 2-enamino-ketonitriles

Abstract

The present invention relates to novel phenyl-substituted 2-enamino-ketonitriles of the formula (I): in which Ar, X, Z, Y and K are each as defined in the description, to a plurality of processes for their preparation and to their use as herbicides and pesticides.

1 - 10 . (canceled)  
   
   
       11 . The compound of formula (I)  
     
       
         
         
             
             
         
       
     
     wherein 
 K represents oxygen or sulphur,  
 Ar represents Ar 1 , where Ar 1  represents phenyl which is mono- to trisubstituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy, allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylenedioxy, tetrafluoroethylenedioxy, difluoromethylthio, trifluoromethylthio, trifluoro-methylsulphinyl, trifluoromethylsulphonyl, benzyloxy, hydroxyl, mercapto, cyano or amino, or represents pyridyl which is mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, propoxy, i-propoxy, butoxy, i-butoxy, methylthio, ethylthio or trifluoromethyl,  
  or represents Ar 2 , where Ar 2  represents Ar 1  which is additionally substituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl or phenoxy, where these substituents are for their part mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- or t-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano,  
  or represents the group  
                     
  where B 1  represents hydrogen or fluorine and B 8  represents allyl, propargyl or benzyl,  
 X represents  
                     
 Y represents hydrogen, in each case optionally mono- or poly-hydroxy-substituted C 1 -C 6 -alkyl, C 1 -C 4 -halogenoalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkinyl, C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, di-C 1 -C 2 -alkoxy-C 2 -C 4 -alkyl, C 1 -C 2 -alkoxy-C 2 -C 4 -cyanoalkyl, C 1 -C 2 -alkylthio-C 2 -C 3 -alkyl, C 1 -C 5 -halogenoalkenyl or C 1 -C 6 -cyanoalkyl, represents in each case optionally methyl-, methoxy-, ethoxy-, trifluoromethyl-, cyano-, chlorophenyl-, benzyl-, hydroxymethyl-, fluorine- or chlorine-substituted C 3 -C 6 -cycloalkyl or C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl in which optionally one methylene group may be replaced by oxygen or sulphur, represents benzyl, phenethyl or pyridylmethyl, each of which is optionallymono- to trisubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro,  
 Z represents hydrogen, methyl, ethyl, represents phenyl or benzyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,  
 R 3  represents methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, vinyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, represents phenyl, pyridyl or benzyl, each of which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, n-, s-, i- or t-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or in the case of the radicals a), c) and f) mentioned under Ar, also represents the group  
                     
 R 5  represents hydrogen or methyl,  
 R 6  represents hydrogen, methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl, cyclopentyl, cyclohexyl, represents phenyl which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,  
 R 7  represents hydrogen, methyl or ethyl, or  
 R 6 , R 7  furthermore together with the nitrogen atom to which they are attached represent a pyrrolidine, piperidine or morpholine radical;  
 provided that the compound of formula (I) is not:  
 (a) wherein K is O, Ar is p-fluorophenyl, X is CN, Z is methyl, and Y is hydrogen or methyl or n-butyl; or  
 (b) wherein K is O, Ar is 2,4-dichloro-5-fluorophenyl or 2,4-dichlorophenyl, X is CN, Z is hydrogen, and Y is cyclopropyl.  
 
   
   
       12 . The compound according to  claim 11 , wherein 
 K represents oxygen,    Ar represents phenyl which is mono- or polysubstituted by trifluoromethyl, fluorine, chlorine, allyloxy, cyano, benzyloxy, or represents the group                           where particular emphasis is given to the meanings 4-chlorophenyl, 3,5-di(trifluoromethyl)phenyl and 2-fluoro-4-chloro-5-allyloxy,    X represents CN,    Y represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -halogenoalkyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl,    Z represents hydrogen or methyl.