Novel benzamidoxime derivatives, intermediates and process for their preparation, and their use as fungicides

Abstract

Benzamidoxime derivatives of the formula I where: R 1 is hydrogen or fluorine, R 2 is phenyl-C 1 -C 6 -alkyl which may carry one or more substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy on the phenyl ring, or is thienyl-C 1 -C 4 -alkyl, which may carry one or more substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, or is pyrazolyl-C 1 -C 4 -alkyl, which may carry one or more substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, are prepared.

We claim:  
     
         1 . A benzamidoxime derivative of the formula I  
       
         
           
           
               
               
           
         
         where: 
 R 1  is hydrogen or fluorine,  
 R 2  is phenyl-C 1 -C 6 -alkyl which may carry one or more substituents selected from the group consisting of halogen, C—C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy on the phenyl ring, or 
 is thienyl-C 1 -C 4 -alkyl, which may carry one or more substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, or  
 is pyrazolyl-C 1 -C 4 -alkyl, which may carry one or more substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.  
 
 
       
     
     
         2 . A benzamidoxime derivative of the formula I as claimed in  claim 1 , in which R 2  is benzyl which may carry one to three substituents selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy on the phenyl ring.  
     
     
         3 . A benzamidoxime of the formula III  
       
         
           
           
               
               
           
         
       
     
     
         4 . A benzamidoxime of the formula IV  
       
         
           
           
               
               
           
         
       
       where R 1  and R 2  are as defined in  claim 1 .  
     
     
         5 . The use of benzamidoxime derivatives of the formula I as claimed in  claim 1  for controlling harmful fungi.  
     
     
         6 . A process for preparing the benzamidoxime derivatives of the formula I as claimed in  claim 1 , which comprises reacting benzonitriles of the formula II with hydroxylamine or salts thereof in aqueous solution, preferably at a pH greater than 8, to give benzamidoximes of the formula III (R 1 =H or F) which are subsequently alkylated with a cyclopropylmethyl halide to give benzamidoximes of the formula IV which are subsequently converted into benzamidoxime derivatives of the formula I using an appropriate acyl halide.  
     
     
         7 . A fungicidal composition, comprising a fungicidally effective amount of at least one benzamidoxime derivative of the formula I.  
     
     
         8 . A method for controlling harmful fungi, which comprises treating the harmful fungi, their habitat or the plants, areas, materials or spaces to be kept free from them with a fungicidally effective amount of a compound of the formula I or a fungicidal composition comprising a benzamidoxime derivative of the formula I as claimed in  claim 7.