This is paper number 43 in a series describing the synthesis of lactones that show biological activity.
Lactones 43. New biologically active lactones: β-cyclocitral derivatives†
Version of Record online: 1 JUL 2013
© 2013 Society of Chemical Industry
Pest Management Science
Volume 70, Issue 2, pages 286–294, February 2014
How to Cite
Mazur, M., Gładkowski, W., Podkowik, M., Bania, J., Nawrot, J., Białońska, A. and Wawrzeńczyk, C. (2014), Lactones 43. New biologically active lactones: β-cyclocitral derivatives. Pest. Manag. Sci., 70: 286–294. doi: 10.1002/ps.3557
- Issue online: 13 JAN 2014
- Version of Record online: 1 JUL 2013
- Accepted manuscript online: 22 MAY 2013 11:05AM EST
- Manuscript Accepted: 22 MAY 2013
- Manuscript Revised: 28 MAR 2013
- Manuscript Received: 6 FEB 2013
- feeding deterents;
- antifeedant activity;
- antibacterial compound
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.
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.
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