Intermediates for pesticidal composition comprising enantiomeric form of fipronil

Abstract

A compound having the formula: wherein E is an organic radical which is enantiomerically enriched.

What is claimed is:  
     
         1 . A compound having the formula:  
       
         
           
           
               
               
           
         
       
       wherein E is an organic radical which is enantiomerically enriched.  
     
     
         2 . A compound according to  claim 1 , wherein E is an organic radical which is substantially enantiomerically pure.  
     
     
         3 . A compound according to  claim 1 , wherein the organic radical E is derived from a compound EG wherein G is a group reactive with amino which is a carboxylic acid, carboxylic acid anhydride, carboxylic acid halide or other carboxylic acid derivative.  
     
     
         4 . A compound according to  claim 1 , wherein the organic radical E comprises a primary amine, secondary amine or tertiary amine.  
     
     
         5 . A compound according to  claim 1 , wherein the radical E comprises a carboxylic acid or sulfonic acid.  
     
     
         6 . A compound according to  claim 1 , having formula (III-A).  
     
     
         7 . A compound according to  claim 1 , having formula (III-B).  
     
     
         8 . A compound according to  claim 6 , wherein E is an organic radical which is substantially enantiomerically pure.  
     
     
         9 . A compound according to  claim 7 , wherein E is an organic radical which is substantially enantiomerically pure.  
     
     
         10 . A process for the preparation of a composition comprising (S)-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole and (R)-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole, enriched in the (S) enantiomer, said process comprising: 
 (a) reacting a compound of the formula:                          with a compound of the formula EG wherein E is an organic radical which is enantiomerically enriched and G is a group reactive with the amino which is a carboxylic acid, carboxylic acid anhydride, carboxylic acid halide or other carboxylic acid derivative to provide compounds of the formula                          wherein E is defined as above;    (b) separating the compounds of formulas (III-A) and (III-B); and    (c) removing the groups EC(O) from the compounds of formulas (III-A) and (III-B) by hydrolysis to afford the composition comprising (S)-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole and (R)-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinylpyrazole, enriched in the (S) enantiomer.    
     
     
         11 . A process according to  claim 10  wherein E is an organic radical which is substantially enantiomerically pure.  
     
     
         12 . A process according to  claim 10 , wherein the organic radical E comprises a primary amine, secondary amine or tertiary amine.  
     
     
         13 . A process according to  claim 10 , wherein the organic radical E comprises a carboxylic acid or sulfonic acid.  
     
     
         14 . A process according to  claim 10 , wherein EG is a Moscher acid halide, an activated Evans chiral auxiliary, an activated sugar moiety or a protected and activated amino acid.  
     
     
         15 . A process according to  claim 12 , wherein the products of step (a) are two diasteriomers which are converted to the corresponding acid addition salts and then separated.  
     
     
         16 . A process according to  claim 15 , wherein the salts are separated by fractional crystallization.  
     
     
         17 . A process according to  claim 13 , wherein the products of step (a) are two diasteriomers which are converted to the corresponding salts and then separated.  
     
     
         18 . A process according to  claim 17 , wherein the salts are separated by fractional crystallization.