Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives
MetadatosMostrar el registro completo del ítem
AutorGalisteo Pretel, Alberto; Pérez del Pulgar, Helena; Sonia Olmeda, A.; González Coloma, Azucena; Fernández Barrero, Alejandro; Quílez Del Moral, José Francisco
Organic synthesisNatural productsPesticidesAntiticksAntifeedant
Galisteo Pretel, A., Pérez del Pulgar, H., Olmeda, A. S., Gonzalez-Coloma, A., Barrero, A. F., & Quílez del Moral, J. F. (2019). Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives. Biomolecules, 9(11), 742.
PatrocinadorThis research was funded by Grant CTQ-2015-64049-C3-3-R / CTQ2015-64049-C3-1-R; Ministerio de Economía y Competitividad, Spain (MINECO/FEDER).
Naturally occurring nootkatone, with reported insecticidal and acaricidal properties, has been used as a lead to generate molecular diversity and, consequently, new insect antifeedant and ixodicidal compounds. A total of 22 derivatives were generated by subjecting this molecule to several reactions including dehydrogenation with the iodine/DMSO system, oxidation with SeO2, epoxidation with mCPBA, oxidation or carbon homologations of the -carbonyl position with TMSOTf (trimethylsilyl trifluoromethanesulfonate) followed by Rubottom and Dess Martin periodane oxidations, condensation with formaldehyde using Yb(OTf)3 as catalyst and dehydroxilation using the Grieco protocol. The insect antifeedant (against Myzus persicae and Ropaloshysum padi) and ixodicidal (against the tick Hyalomma lusitanicum) activities of these compounds were tested. Compound 20 was the most active substance against M. persicae and R. padi, and twice more e cient than nootkatone in the antitick test.