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Open AccessArticle

Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives

1
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, Spain
2
Faculty of Veterinary, Complutense University of Madrid (UCM), 28040 Madrid, Spain
3
Institute of Agricultural Sciences, CSIC, 28006, Madrid, Spain
*
Authors to whom correspondence should be addressed.
Biomolecules 2019, 9(11), 742; https://doi.org/10.3390/biom9110742
Received: 26 September 2019 / Revised: 6 November 2019 / Accepted: 12 November 2019 / Published: 16 November 2019
(This article belongs to the Section Natural and Bio-inspired Molecules)
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. View Full-Text
Keywords: organic synthesis; natural products; pesticides; antiticks; antifeedant organic synthesis; natural products; pesticides; antiticks; antifeedant
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MDPI and ACS Style

Galisteo Pretel, A.; Pérez del Pulgar, H.; Olmeda, A.S.; Gonzalez-Coloma, A.; Barrero, A.F.; Quílez del Moral, J.F. Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives. Biomolecules 2019, 9, 742.

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