Biodegradation of hexachlorocyclohexane isomers in soil and food environment.

Persistence of chlorinated hydrocarbon insecticides in the environment is well documented. One early introduced insecticide, hexachlorocyclohexane (HCH), popularly called BHC, was used in large quantities all over the world until recently. In India, even today, technical grade HCH is being used extensively. Theoretically, HCH has eight possible stereoisomers of which four (alpha, beta, gamma, and delta) predominate in the technical product. These isomers significantly differ between themselves with respect to their persistence and toxicity toward insects, birds, mammals, and other nontarget organisms. The relative proportion of HCH isomers is, therefore, crucial from a toxicology standpoint. This problem assumes importance in light of reports that the HCH isomers undergo interconversion in soil, water, animals, plants, insects, etc. The persistence of HCH can be attributed in part to the interconversion of HCH isomers, which also restrict their solubility. In the present review, biotransformation of HCH isomers, both under aerobic and anaerobic conditions, and their degradation pathways have been described. In addition, emphasis is given to the interconversion of HCH isomers, including interconversion mechanisms, as this area has not received adequate coverage in earlier reviews on HCH.

Interconversions and toxicity changes in hexachlorocyclohexane isomers on dispersion in water.

Studies on the transformations of hexachlorocyclohexane isomers, alpha-, beta-, gamma- and delta-, in aqueous solution were carried out at 25 +/- 1 degree C over a period of four weeks. Gas liquid chromatographic technique was used for analysis. The results indicated a loss as well as interconversion of all the four isomers with time. The resulting changes in toxicity of the aqueous solution were studied against Drosophila using topical application. Toxicity studies with aqueous solution of technical hexachlorocyclohexane were simultaneously carried out for comparison. Toxicity of the aqueous solutions of alpha-, beta-, and delta- isomers showed an increase while that of the gamma- isomer decreased significantly during the four week experimental period. Aqueous solution of technical HCH was equally toxic as that of the gamma- isomer initially and did not show much decrease in its toxicity at the end. Changes in toxicity of the individual isomer solutions were considered to be due, in part, to interconversions of HCH isomers.

Isomerization of beta-HCH in aqueous solution.

beta-HCH was shaken with distilled water at 25 +/- 1 degree C for different time intervals and filtered. The ether extract of the filtrate on analysis by gas liquid chromatography showed the presence of four isomers, alpha, beta, gamma and delta, besides other compounds, thereby indicating isomerization of the beta-isomer in aqueous solution. Further, the ether extract, when dried and dissolved in acetone, showed high toxicity to mosquito larvae, flour beetle larvae and house-flies thereby indicating conversion of the inert beta-isomer to more toxic forms corroborating GLC analysis. Acetone solution of pure beta-HCH was found nontoxic against the insects tested.

Ring hydroxylation of p-chlorophenylacetate by an arthrobacter strain.

Resting cell suspensions of a strain of Arthrobacter grown on phenylacetate converted p-chlorophenylacetate to two products. One of the products was identified as 4-chloro-3-hydroxyphenylacetate.