Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives
Metadatos
Mostrar el registro completo del ítemAutor
Galisteo Pretel, Alberto; Pérez del Pulgar, Helena; Sonia Olmeda, A.; González Coloma, Azucena; Fernández Barrero, Alejandro; Quílez Del Moral, José FranciscoEditorial
MDPI
Materia
Organic synthesis Natural products Pesticides Antiticks Antifeedant
Fecha
2019-11-16Referencia bibliográfica
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.
Patrocinador
This research was funded by Grant CTQ-2015-64049-C3-3-R / CTQ2015-64049-C3-1-R; Ministerio de Economía y Competitividad, Spain (MINECO/FEDER).Resumen
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.