COMPARATIVE METABOLISM OF ENANTIOMERS OF CHLORDENE AND CHLORDENE EPOXIDE IN GERMAN COCKROACHES, IN RELATION TO THEIR REMARKABLY DIFFERENT INSECTICIDAL ACTIVITY

Both enantiomers (optically pure) of chlordene and chlordene epoxide were metabolized in German cockroaches in order to clarify the remarkable difference of toxicity between both enantiomers of these insecticides. Of four metabolic products of (+)- and (-)-chlordenes, the amount of chlordene epoxide produced from (+)-chlordene was about sevenfold larger than that from its (-) enantiomer, and this amount was comparable to the unmetabolized (-)-chlordene epoxide remaining after application of an amount comparable in toxicity to that of (+)-chlordene. These results, combined with our previous findings that (+)-chlordene produced chemically its (-) epoxide, and both (-)-chlordene and its oxidized (+) epoxide had no activity, unambiguously indicated that (-)-chlordene epoxide was insecticidal, per se, while (-t-)-chlordene was insecticidal after metabolic conversion to the corresponding (-) epoxide. © 1979, American Chemical Society. All rights reserved.