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House flies, Musca domestica (L.), and their eggs were treated with 22 monoterpenoids to determine the topical, fumigant, and ovicidal activity of each compound. Fumigant activity of 14 monoterpenoids were examined further using red flour beetles, Tribolium castaneum (Herbst). Third-instar southern corn rootworm, Diabrotica undecimpunctata howardi Barber, were treated with carvacrol, citral, citronellal, menthol, pulegone, verbenol, and verbenone to determine their activity on larvae. Structure-activity relationships were evaluated with the toxicity data. We made comparisons between monocyclic aromatic, acyclic aliphatic, monocyclic aliphatic, and bicyclic aliphatic alcohols, ketones, aldehydes, and acids to determine toxicity differences involving the skeletal structure, amount of saturation, and associated functional groups of monoterapenoids. Ketones were more effective than alcohols in the topical, fumigant (T. castaneum), and ovicidal bioassays and less toxic than an analogous aldehyde in the topical, fumigant (M. domestica), and ovicidal bioassays. Aldehydes were more toxic than alcohols in the topical and fumigant (M. domestica) bioassays. In the topical and ovicidal bioassays, aromatic or acyclic alcohols, or both, were more effective than monocyclic and bicyclic alcohols. Vapors of bicyclic ketones were more toxic than monocyclic ketones to adult M. domestica. Monoterpenoid alcohols containing three carbon-carbon double bonds were more effective than saturated alcohols in the topical and larval bioassays. A mono-unsaturated ketone was more toxic than a structurally similar saturated ketone and two di-unsaturated ketones when it was applied topically to adult M. domestica. A saturated monocyclic ketone inhibited egg hatch more effectively than unsaturated monocyclic ketones.
Rice et al. (Sat,) studied this question.