Glucosinolate aglucones and analogues: insecticidal properties and a QSAR

Naturally occurring aglucones of three glucosinolates (sinigrin, glucotropaeolin, and epi-progoitrin) were tested for fumigation activity against the house fly, Musca domestica, and the lesser grain borer, Rhizopertha dominica. A total of eight natural aglucones were evaluated in the bioassays. Two aglucones of sinigrin showed efficacy against both species which was comparable with that of a commercial fumigant, chloropicrin. None of the aglucones tested was comparable in activity to dichlorvos. Aglucones of glucotropaeolin were also insecticidal, but not to the same level as the sinigrin aglucones. The aglucones of epi-progoitrin were only slightly effective as fumigants. A quantitative structure–activity relationship (QSAR) was developed for synthetic analogues of the sinigrin and glucotropaeolin aglucones. An electronic parameter, σ*, provided the best predictor of activity in R. dominica, whereas a hydrophobicity parameter, π, best predicted activity in M. domestica.