Degradation of juvenogens by termites and soil bacteria

Abstract

Considering a potential application of selected biochemically activated insect hormonogen substances (juvenogens) against pest termite species, we aimed this study to describe the metabolism of these compounds by termites and soil bacteria and to evaluate the potential impact of their metabolites on the environment. Radiolabelled derivatives of the juvenogens cis- and trans-isomers of ethyl N-{2-[4-(2-butanoyloxycyclohexyl)methyl]phenoxy}ethyl carbamate were metabolized by the termite Reticulitermes flavipes and the bacteria Bacillus simplex and Bacillus sp., strain 05 (GenBank EU399813) giving rise to different numbers of metabolites. The trans-isomer of the juvenogen was metabolized by both Bacillus species into its parent synthetic structure, ethyl trans- N-{2-[4-(2-hydroxycyclohexyl)methyl]phenoxy}ethyl carbamate, while the cis-isomer was metabolized into further products. Both racemic juvenogens were metabolized bytermites, affording mainly the parent juvenoids. In terms of ecotoxicity, the trans-juvenogen shows a significantly lower toxicity than the cis-juvenogen. In contrast, the toxicity of the cis-juvenoid (main degradation product of cis-juvenogen) is higher than the toxicity of trans-juvenoid (main degradation product of trans- juvenogen). The precursors of the two juvenogens cis- and trans-2-(4-hydroxybenzyl)cyclohexanol were also tested but exhibited a low toxicity. The results demonstrate that bacteria can metabolize the juvenogen in liquid media culture and have implications for the development of a strategy for bioremediation of soil. Moreover, the products of the biodegradation exhibited low toxicity. Both juvenogens have a high juvenilizing effect, cause low mortality and are stable within a period of two weeks.