Enantiomeric resolution and biotoxicity of methamidophos

Abstract

Despite the fact that the biological processes of chiral pesticides are enantioselective, the biotoxicity of methamidophos with respect to enantioselectivity has so far received limited research. In this study, the enantiomeric separation and biotoxicity of the two enantiomers of methamidophos were investigated. Successful enantioseparation of methamidophos using high-performance liquid chromatography on a Chiralcel OD column was achieved. As indicated by the optical rotation and circular dichroism detection, (+)-methamidophos was eluted prior to (-)-methamidophos. The t test at the 95% level of confidence indicated significant differences between the enantiomers in their in vitro inhibition toward acetylcholinesterases of bovine erythrocytes and Electrophorus electricus and in vivo acute aquatic toxicity to Daphnia magna. The in vitro assays showed that (-)-methamidophos was about 8.0-12.4 times more potent to the enzymes than its (+)-form. In contrast, the (+)-enantiomer was 7.0 times more toxic to D. magna in 48 h tests. The toxicity of racemic methamidophos was intermediate in both in vitro and in vivo bioassays. These results suggest that the biotoxicity of chiral OPs to nontargeted organisms is enantioselective and therefore should be reevaluated with their pure enantiomers.