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.
Highlights
The well-known advantages of biopesticides compared to conventional synthetic pesticides account for the increasing number of research papers published in this field in recent years [1,2]
Conventional pesticides and biopesticides can be categorized according to the origin of their active ingredients, with one of these categories encompassing synthetic natural derived (SND) substances [2]
We focused our attention on nootkatone (1), a sesquiterpene which was isolated for the first time from the essential oil of the heartwood of Alaska yellow cedar (Cupressus nootkatensis) [3,4], and is present in plants of Citrus genus [5], Vetiveria species [6] and others natural sources [7]
Summary
The well-known advantages of biopesticides compared to conventional synthetic pesticides account for the increasing number of research papers published in this field in recent years [1,2]. Conventional pesticides and biopesticides can be categorized according to the origin of their active ingredients, with one of these categories encompassing synthetic natural derived (SND) substances [2] In this context, we focused our attention on nootkatone (1), a sesquiterpene which was isolated for the first time from the essential oil of the heartwood of Alaska yellow cedar (Cupressus nootkatensis) [3,4], and is present in plants of Citrus genus [5], Vetiveria species [6] and others natural sources [7].
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