Pentachlorocyclohexene as a possible Intermediate Metabolite of Benzene Hexachloride in Houseflies

Abstract

STERNBERG and Kearns¹ have reported that both γ-benzene hexachloride (γ-BHC)-resistant and susceptible houseflies can dehydrochlorinate γ-BHC to pentachlorocyclohexene (PCCH). Their evidence relied on the formation of 1-chloro-2:4-dinitro-benzene when the method of Schecter and Hornstein² for the determination of γ-BHC was applied to flies treated with the insecticide. This method involved the reduction with zinc and acetic acid of unchanged γ-BHC and PCCH to benzene and chlorobenzene followed by nitration to form m-dinitrobenzene and 1-chloro-2:4-dinitrobenzene respectively. Bradbury and Standen³, working with a different strain of resistant and susceptible houseflies, used an isotopic dilution technique to determine any γ-PCCH present after γ-BHC treatment but failed to find the large amounts reported by Sternberg and Kearns.