Effect of Oxygen Incorporation into Cyclohexanone Ring on Antifeedant Activity
2011
Dancewicz, Katarzyna | Ratuś, Barbara | Boratyński, Filip | Kordan, Bożena | Gabryś, Beata | Wawrzeńczyk, Czesław
The behaviour of the peach potato aphid Myzus persicae (Sulz.) was studied during settling on plants. The experiment involved observing peach potato aphid activity after the application of some natural and synthetic cyclohexanones and the, respective ε-lactones and epoxy-ε-lactones which were obtained from the cyclohexanones. Stereochemistry, and the number and position of methyl substituents were important for the biological activity of the starting compounds: only trimethyl-substituted cyclohexanones were active, i.e. 3.3.5-trimethylcyclohexanone (deterrent) and 2.2.6-trimethylcyclohexanone (attractant). The effect of oxygen incorporation into the cyclohexanone ring on deterrent activity varied depending on the starting compound. The ε-lactones that derived from saturated cyclohexanones were either weak attractants or were inactive, except the deterrent ε-lactone with three methyl groups at positions 3.7.7. None of the products of unsaturated ketone isophorone (weak deterrent) oxidation, i.e. epoxy isophorone, epoxy lactone, or unsaturated lactone, affected aphid settling. Of the two epoxy ketones obtained from (+)-dihydrocarvone that was inactive, only (2S, 5S)-2-methyl-5-((S)-1-methyloxiranyl)-cyclohexanone was a strong deterrent. Both epoxy-ε-lactones that derived from (+)-dihydrocarvone were strong deterrents.
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