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

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Galisteo Pretel, Alberto and Pérez del Pulgar, Helena and Guerrero de León, Estela and López-Pérez, José Luis and Olmeda García, Ángeles Sonia and Gonzalez-Coloma, Azucena and F. Barrero, Alejandro and Quílez del Moral, José Francisco (2019) Germacrone Derivatives as new Insecticidal and Acaricidal Compounds: A Structure-Activity Relationship. Molecules, 24 (16). p. 2898. ISSN 1420-3049

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Official URL: https://doi.org/10.3390/molecules24162898




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 (2–24). 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.


Item Type:Article
Uncontrolled Keywords:natural products; organic synthesis; bioactive compounds; insecticidal; ixodicidal
Subjects:Medical sciences > Veterinary > Agriculture
ID Code:65103
Deposited On:26 Apr 2021 15:55
Last Modified:27 Apr 2021 06:54

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