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

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

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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 Omega 3 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 VIT E 14 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.