Heterocycle-substituted, n-phenyl-phthalamide derivatives, related compounds and their use as insecticides

Abstract

Novel benzenedicarboxamides of the formula (I) wherein X represents hydrogen, halogen atom, nitro, C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfenyl or C 1-6 alkylsulfonyl, R 1 represents C 1-6 alkyl, C 1-6 alkylthio-C 1-6 alkyl, C 1-6 alkylsulfinyl-C 1-6 alkyl or C 1-6 alkylsulfonyl-C 1-6 alkyl, Y represents halogen or C 1-6 alkyl, m represents 0 or 1, A represents O, S, SO, SO 2 , CH 2 or CH(CH 3 ), and Q represents a 5- or 6-membered heterocyclic group that contains at least one hetero atom selected from the group consisting of N, O and S and can be optionally substituted; processes for their preparation, their intermediates and their use as insecticides.

1 - 3 . (canceled) 
   
   
       4 . A process for the preparation of a compound of formula (I), 
     
       
         
         
             
             
         
       
       wherein 
       X represents hydrogen, halogen, nitro, C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfenyl or C 1-6 alkylsulfonyl, 
       R 1  represents C 1-6 alkyl, C 1-6 alkylthio-C 1-6 alkyl, C 1-6 alkylsulfinyl-C 1-6 alkyl or C 1-6 alkylsulfonyl-C 1-6 alkyl, 
       Y represents halogen or C 1-6 alkyl, 
       m represents 0 or 1, 
       A represents O, S, SO, SO 2 , CH 2  or CH(CH 3 ), and 
       Q represents a 5-membered or 6-membered heterocyclic group that contains at least one hetero atom selected from the group consisting of N, O and S and can be optionally substituted; 
       comprising
 (a) reacting a compound of formula (II) 
 
     
     
       
         
         
             
             
         
       
       
         
           wherein R 1  and X have the same definition as above, with a compound of formula (III) 
         
       
     
     
       
         
         
             
             
         
       
       
         
           wherein Y, A, m and Q have the same definition as above, in the presence of an inert solvent, and optionally in the presence of an acid catalyst, or 
         
         (b) reacting a compound of formula (IV) 
       
     
     
       
         
         
             
             
         
       
       
         
           wherein X, Y, A, m and Q have the same definitions as above with a compound of formula (V)
   H 2 N—R 1   (V) 
 
           wherein R 1  has the same definition as above, in the presence of an inert solvent, and optionally in the presence of an acid catalyst, or 
         
         (c) reacting a compound of formula (VI) 
       
     
     
       
         
         
             
             
         
       
       
         
           wherein X and R 1  have the same definitions as above, with a compound of formula (III), 
         
       
     
     
       
         
         
             
             
         
       
       
         
           wherein Y, A, m and Q have the same definition as above, in the presence of an inert solvent, and optionally in the presence of an acid catalyst, or 
         
         (d) reacting a compound of formula (VII) 
       
     
     
       
         
         
             
             
         
       
       
         
           wherein X, Y, A, m and Q have the same definitions as above, with a compound of formula (V),
   H 2 N—R 1   (V) 
 
           wherein R 1  has the same definitions as above, in the presence of an inert solvent, and optionally in the presence of an acid catalyst, or 
         
         (e) reacting a compound of formula (VIII) 
       
     
     
       
         
         
             
             
         
       
       
         
           wherein X, Y, A, m and Q have the same definitions as above, with a compound of formula (V),
   H 2 N—R 1   (V) 
 
           wherein R 1  has the same definitions as above, in the presence of an inert solvent, and optionally in the presence of an acid catalyst, or 
         
         (f) in case where R 1  represents C 1-6 alkylsulfinyl-C 1-6 alkyl or C 1-6 alkylsulfonyl-C 1-6 alkyl in formula (I): reacting a compound of formula (If) 
       
     
     
       
         
         
             
             
         
       
       
         
           wherein 
           R If  represents C 1-6 alkylthio-C 1-6 alkyl, and 
           X, Y, A, m and Q have the same definitions as above, with an oxidizing agent in the presence of an inert solvent. 
         
       
     
   
   
       5 - 9 . (canceled) 
   
   
       10 . A compound of formula (VII) 
     
       
         
         
             
             
         
       
       wherein 
       X represents hydrogen, halogen, nitro, C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfenyl or C 1-6 alkylsulfonyl, 
       Y represents halogen or C 1-6 alkyl, 
       A represents O, S, SO, SO 2 , CH 2  or CH(CH 3 ), 
       m represents 0 or 1, and 
       Q represents a 5-membered or 6-membered heterocyclic group that contains at least one hetero atom selected from the group consisting of N, O and S and can be optionally substituted. 
     
   
   
       11 . (canceled) 
   
   
       12 . A compound of formula (IX) 
     
       
         
         
             
             
         
       
       wherein 
       X represents hydrogen, halogen, nitro, C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfinyl, C 1-6 alkylsulfenyl or C 1-6 alkylsulfonyl, 
       Y represents halogen or C 1-6 alkyl, 
       A represents O, S, SO, SO 2 , CH 2  or CH(CH 3 ), 
       m represents 0 or 1, and 
       Q represents a 5-membered or 6-membered heterocyclic group that contains at least one hetero atom selected from the group consisting of N, O and S and can be optionally substituted.