Lactones 43. New biologically active lactones: β-cyclocitral derivatives.

Mazur, Marcelina; Gładkowski, Witold; Podkowik, Magdalena; Bania, Jacek; Nawrot, Jan; Białońska, Agata; Wawrzeńczyk, Czesław

BACKGROUND In our previous studies bicyclic γ-lactones with cyclohexane ring exhibited high antifeedant activity against storage pests. The activity was correlated with the type and number of substituents in the cyclohexane ring. One of the most potent group of antifeedant agents was δ-iodo- γ-lactones. RESULTS We present the synthesis of new bicyclic γ-lactones with the cyclohexane ring containing different halogen atoms. To determine the impact of halogen type on biological activity the lactone without halogen atom was also synthesized. The lactones were tested for their antifeedant activity toward the granary weevil beetle ( Sitophilus granarius L.), the khapra beetle ( Trogoderma granarium Everts) and the confused flour beetle ( Tribolium confusum Du Val.). The results of the tests proved that the highest activity was observed for chlorolactone (7) towards larvae and adults of Tribolium confusum. Antibacterial activity of new lactones was also evaluated. Lactone without halogen atom (8) was active against Staphylococcus aureus and Listeria monocytogenes. CONCLUSIONS Studies on the biological activity of synthesised lactones revealed high selectivity towards insect pests as well as bacterial strains. Only the halolactones exhibited significant antifeedant activity. In contrast, antibacterial activity was shown only by the lactone (8) without halogen. © 2013 Society of Chemical Industry

LACTONES; CYCLOHEXANE; ANTIFEEDANTS; HALOGENS; GRANARY weevil; CONFUSED flour beetle; STAPHYLOCOCCUS aureus

Pest Management Science, 2014, Vol 70, Issue 2, p286

1526-498X

Academic Journal

10.1002/ps.3557