Soil as a Source of Atmospheric Heptachlor Epoxide

The chiral pesticide heptachlor can undergo photolysis to yield the racemic products heptachlor-exo-epoxide (HEPX) and photoheptachlor. Heptachlor is also metabolized to nonracemic HEPX in biological systems and soils. HEPX in ambient air samples from the southern United States and Lakes Ontario and Superior was nonracemic and enriched in the (+) enantiomer. Average enantiomer ratios (ER = areas of (+)/(−) HEPX) in these locations ranged from 1.51 to 2.02, and were similar to ER values of HEPX reported for agricultural soils. Airborne heptachlor was racemic, with ERs of 0.98−1.02. These results suggest that the main source of HEPX in ambient air is not photolysis of heptachlor, but rather metabolism of heptachlor in soils followed by volatilization of HEPX. The study exemplifies the use of chiral analysis for investigating the environmental fate of pesticides.