Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives

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Galisteo Pretel, Alberto and Pérez del Pulgar, Helena and Olmeda García, Ángeles Sonia and Gonzalez-Coloma, Azucena and Barrero, Alejandro F. and Quílez del Moral, José Francisco (2019) Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives. Biomolecules, 9 (11). p. 742. ISSN 2218-273X

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Official URL: https://doi.org/10.3390/biom9110742




Abstract

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 α-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 efficient than nootkatone in the antitick test.


Item Type:Article
Uncontrolled Keywords:organic synthesis; natural products; pesticides; antiticks; antifeedant
Subjects:Medical sciences > Veterinary > Microbiology
ID Code:64482
Deposited On:23 Mar 2021 15:23
Last Modified:25 Mar 2021 08:13

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