ORIGINAL ARTICLE
Effect of oxygen incorporation into cyclohexanone ring on antifeedant activity
1
Department of Botany and Ecology, University of Zielona Góra
Szafrana 1, 65-516 Zielona Góra, Poland
2
Department of Chemistry, University of Environmental and Life Sciences
Norwida 25, 50-375 Wrocław, Poland
3
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
KEYWORDS
TOPICS
ABSTRACT
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.
CONFLICT OF INTEREST
The authors have declared that no conflict of interests exist.
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