Stereoselective degradation of diclofop‐methyl during alcohol fermentation process

Abstract Stereoselective degradation of Diclofop‐methyl (DM) has been found in alcohol fermentation of grape must and sucrose solution with dry yeast. A method was developed for separation and determination the two enantiomers of DM during the fermentation process by high‐performance liquid chromatography based on cellulose tri‐(3,5‐dimethylphenyl‐carbamate) chiral stationary phase. The results showed that the enantiomers of DM degraded following the first‐order kinetics in the sucrose solution and the degradation of DM enantiomers in grape must were biphasic (slow‐fast‐slow process). In the sucrose solution, half lives of (+)‐( R )‐DM and (−)‐( S )‐DM were calculated to be 8.5 h and 3.1 h, respectively. In the grape must, half life of (+)‐( R )‐DM was calculated to be 41.7 h while (−)‐( S )‐DM was 16.0 h. The result was that (−)‐( S )‐enantiomer degraded faster than the (+)‐( R )‐enantiomer in both alcohol fermentation. The results also showed that the differences of the enantioselective degradation of DM depended on the fermentation matrix. DM was configurationally stable in fermentation, showing no interconversion of (−)‐( S )‐ to (+)‐( R )‐ enantiomer, and vice‐versa. Chirality, 2011. © 2011 Wiley‐Liss, Inc.