Effect of oxygen incorporation into cyclohexanone ring on antifeedant activity
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Department of Botany and Ecology, University of Zielona Góra Szafrana 1, 65-516 Zielona Góra, Poland
Department of Chemistry, University of Environmental and Life Sciences Norwida 25, 50-375 Wrocław, Poland
Department of Phytopathology and Entomology, University of Warmia and Mazury in Olsztyn Prawocheńskiego 17, 10-718 Olsztyn, Poland
Journal of Plant Protection Research 2011;51(1):23–28
The behaviour of the peach potato aphid Myzus persicae (Sulz.) was studied during settling on plants. The experiment in- volved 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 incor - poration 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.
The authors have declared that no conflict of interests exist.
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