Germacrone derivatives as new insecticidal and acaricidal compounds: a structure-activity relationship
| Autor: | José Quilez del Moral, Helena Pérez del Pulgar, Azucena González-Coloma, Alberto Galisteo Pretel, Alejandro F. Barrero, A. Sonia Olmeda, José Luis López-Pérez, Estela Guerrero De León |
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| Přispěvatelé: | Ministerio de Economía y Competitividad (España) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Integrated pest management
Insecticides Pesticide resistance Ixodidae Insecticidal Pharmaceutical Science Organic synthesis Germacrone 010402 general chemistry 01 natural sciences Article Bioactive compounds Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Sesquiterpenes Germacrane Structure-Activity Relationship lcsh:Organic chemistry Rhopalosiphum padi Drug Discovery Structure–activity relationship Animals Physical and Theoretical Chemistry Natural products Natural product Traditional medicine 010405 organic chemistry Agricultura Organic Chemistry Pesticide Ixodicidal 0104 chemical sciences chemistry Chemistry (miscellaneous) Aphids Molecular Medicine PEST analysis |
| Zdroj: | E-Prints Complutense. Archivo Institucional de la UCM instname Digital.CSIC. Repositorio Institucional del CSIC Molecules Volume 24 Issue 16 Digibug. Repositorio Institucional de la Universidad de Granada Molecules, Vol 24, Iss 16, p 2898 (2019) E-Prints Complutense: Archivo Institucional de la UCM Universidad Complutense de Madrid |
| ISSN: | 1420-3049 |
| Popis: | The supplementary material related to this article includes NMR spectra of new compounds is available online at https://www.mdpi.com/1420-3049/24/16/2898/s1. 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. This research was funded by Grant CTQ-2015-64049-C3-3-R/CTQ2015-64049-C3-1-R; MINISTERIO DE ECONOMÍA Y COMPETITIVIDAD, Spain (MINECO/FEDER). |
| Databáze: | OpenAIRE |
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