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Germacrone Derivatives as new Insecticidal and Acaricidal Compounds: A Structure-Activity Relationship

1
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, Spain
2
Department of Pharmacology, Faculty of Medicine, University of Panama, Panama 07156, Panama
3
Department of Pharmaceutical Sciences, IBSAL-CIETUS, University of Salamanca, 37007 Salamanca, Spain
4
Faculty of Veterinary, Complutense University of Madrid (UCM), 28040 Madrid, Spain
5
Institute of Agricultural Sciences, CSIC, 28006 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Academic Editors: David Díez and María Ángeles Castro
Molecules 2019, 24(16), 2898; https://doi.org/10.3390/molecules24162898
Received: 2 July 2019 / Revised: 30 July 2019 / Accepted: 2 August 2019 / Published: 9 August 2019
(This article belongs to the Special Issue Application of Organic Synthesis to Bioactive Compounds)
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Abstract

Currently, the use of synthetic pesticides is the main method of plant protection applied in agri- and horticulture. However, its excessive use leads to the development of pesticide resistance, a contamination of the environment, toxicity to non-target organisms, and risks for human health. With the ultimate aim of contributing to the develop of a more sustainable pest management, we used the natural product germacrone (compound 1), reported to possess significant insecticidal activity, as starting material for the generation of molecular diversity (224). Some of the generated derivatives are natural compounds, such as 1,10-epoxygermacrone (2), 4,5-epoxygermacrone (3), gajutsulactone A (7), germacrol (11), isogermacrone (14), 9-hydroxyeudesma-3,7(11)dien-6-one (19), eudesma-4,7(11),dien-8-one (20), eudesma-3,7(11)-dien-8-one (21) and eudesma-4(15),7(11)-dien-8-one (22). Compounds, 7,11-9,10-diepoxigermacr-4,5-en-8-ol (17), 7,11-epoxieudesma-4,7(11)-dien-8-one (23) and 7,11-epoxieudesma-3,7(11)-dien-8-one (24) are described for the first time. The biocidal activity of most of these compounds was assayed against the tick Hyalomma lusitanicum. The acaricidal effects of compound 24 were four times higher than that of germacrone (1). Compound 2 is an insect antifeedant a thousand times more potent than germacrone against Rhopalosiphum padi, which makes this substance a promising selective antifeedant against this cereal pest. View Full-Text
Keywords: natural products; organic synthesis; bioactive compounds; insecticidal; ixodicidal natural products; organic synthesis; bioactive compounds; insecticidal; ixodicidal
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Galisteo Pretel, A.; Pérez del Pulgar, H.; Guerrero de León, E.; López-Pérez, J.L.; Olmeda, A.S.; Gonzalez-Coloma, A.; F. Barrero, A.; Quílez del Moral, J.F. Germacrone Derivatives as new Insecticidal and Acaricidal Compounds: A Structure-Activity Relationship. Molecules 2019, 24, 2898.

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