The chiral pesticide heptachlor can undergo photolysis to yield the ra
cemic products heptachlor-exo-epoxide (HEPX) and photoheptachlor. Hept
achlor is also metabolized to nonracemic HEPX in biological systems an
d soils. HEPX in ambient air samples from the southern United States a
nd Lakes Ontario and Superior was nonracemic and enriched in the (+) e
nantiomer. Average enantiomer ratios (ER = areas of (+)/(-) HEPX) in t
hese locations ranged from 1.51 to 2.02, and were similar to ER values
of HEPX reported for agricultural soils. Airborne heptachlor was race
mic, with ERs of 0.98-1.02. These results suggest that the main source
of HEPX in ambient air is not photolysis of heptachlor, hut rather me
tabolism of heptachlor in soils followed by volatilization of HEPX. Th
e study exemplifies the use of chiral analysis for investigating the e
nvironmental fate of pesticides.