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.
Capinera J. 2004. Encyclopedia of Entomology. Vol. 1. Kluwer Academic Publishers, Dordrecht, 815 pp.
Dancewicz K., Gabryś B., Halarewicz-Pacan A., Grabarczyk M., Wawreńczyk C. 2005. Effect of terpenoid lactones with di- and trimethylcyclohexane systems on the behaviour of green peach aphid Myzus persicae. Pestycydy 4: 17–23.
Dancewicz K., Gabryś B., Halarewicz-Pacan A., Obara R., Wawrzeńczyk C. 2006. Alkilo podstawione γ- i δ-laktony jako deterenty pokarmowe w stosunku do mszyc. Prog. Plant Protection/Post. Ochr. Roślin 46 (1): 305–311.
Dancewicz K., Gabryś B., Dams I., Wawrzeńczyk C. 2008. Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae(Sulz.) settling and feeding. J. Chem. Ecol. 34 (4): 530–538.
Del Campo M.L., Via S., Caillaud M.C. 2003. Recognition of host specific chemical stimulants in two sympatric host races of the pea aphid Acyrthosiphon pisum. Ecol. Entomol. 28: 405–412.
Gabryś B., Tjallingii W.F. 2002. The role of sinigrin in host plant recognition by aphids during initial plant penetration Entomol. Exp. Appl. 104 (1): 89–93.
Halarewicz-Pacan A., Gabryś B., Dancewicz K., Wawrzeńczyk C. 2003. Enantiospecific effect of limonene and limonene-derived bicyclic lactones on settling and probing behaviour of the peach potato aphid Myzus persicae (Sulz.). J. Plant Protection Res. 43 (2): 133–142.
Hardie J., Holyoak M., Taylor N.J., Griffiths D.C. 1992. The combination of electronic monitoring and video-assisted observations of plant penetration by aphids and behavioural effects of polygodial. Entomol. Exp. Appl. 62: 233–239.
Juza M., Mazzonti M., Morbidelli M. 2000. Simulated moving bed chromatography and its application to chirotechnology. Trends Biotechnol. 18 (3): 108–118.
Klein Gebbinck E.A., Jansen B.J.M., Groot A.D. 2002. Insect antifeedant activity of clerodane diterpenes and related model compounds. Phytochemistry 61 (7): 737–770.
Leszczyński B. 2001. Rola allelozwiązków w oddziaływaniach owady – rośliny. p. 61–86. In: „Biochemiczne Oddziaływania Środowiskowe” (W. Oleszek, K. Głowniak, B. Leszczyński, eds.). Akademia Medyczna, Lublin.
Ley S.V., Toogood P.L. 1990. Insect antifeedants. Chem. Br. 1: 31–35.
Nawrot J., Błoszyk E., Grabarczyk M., Drożdż B. 1982. Deterrent properties of sesquiterpene lactones for the selected storage pests. Prace Nauk. Inst. Ochr. Roślin 24 (1), p. 27.
Pickett J.A., Wadhams L.J., Woodcock C.M. 1994. Attempts to control aphid pests by integrated use of semiochemicals. p. 1239–1246. In: Brighton Crop Protection Conference – Pests and Diseases. British Crop Protection Council, Thornton Heath, UK.
Picman A.K. 1986. Biological activities of sesquiterpene lactones. Biochem. Syst. Ecol. 14 (3): 255–281.
Polonsky J., Bhatnagar S.C., Griffits D.C., Pickett J.A., Woddcock C.M. 1989. Activity of quassinoids as antifeedants against aphids. J. Chem. Ecol. 15 (3):993–998.
Ratuś B., Boratyński F., Nawrot J., Wawrzeńczyk C. 2009.Lactones Part XXXIII. Synthesis and antifeedant activity of alkyl substituted ε-lactones. Przemysł Chemiczny 88 (5): 557–562.
Ratuś B., Grudniewska A., Wawrzeńczyk C. 2006. Lactones 25 [1]. Baeyer-Villiger oxidation of cyclic ketones.p.256–264. In: “Chemistry for Agriculture” (H. Górecki, Z. Dobrzański, P. Kafarski, eds.). Chech-Pol Trade: Prague, Brussels,.
Wawrzeńczyk C., Paruch E., Olejniczak T. 2002. Terpenoid lactones as insect feeding deterrents. p. 206–213. In: “Chemical Products in Agriculture and Environment” (H. Górecki, Z. Dobrzański, eds.). Czech-Pol Trade: Prague.
Wawrzeńczyk W., Grabarczyk M., Szumny A., Gabryś B., Dancewicz K., Nawrot J., Prądzyńska A., Halarewicz-Pacan A. 2003. Lactones 19 [1]. Synthesis and antifeedant activity of lactones with methyl-, dimethyl- and trimethylcyclo-hexane system. p. 117–129. In: “Chemicals in Sustainable Agriculture. Chemistry for Agriculture Vol. 4”. Czech-Pol Trade, Prague.
Wawrzeńczyk C., Dams I., Szumny A., Szczepanik M., Nawrot J., Prądzyńska A., Gabryś B., Dancewicz K., Magnucka E., Gawdzik B., Obara R., Wzorek A. 2005. Synthesis and evaluation of antifeedant, antifungal and antibacterial activity of isoprenoid lactones. Pol. J. Environ. Studies 14: 69–84.
Wawrzyniak M. 1996. The effect of selected plant extracts on the cabbage butterfly, Pieris brassicae L. (Lepidoptera). Pol. J. Entomol. 65 (1–2): 93–99.
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