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

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.

Valorization of the Sabinas Forest Waste (Juniperus phoenicea and Juniperus thurifera) as Source of Biopesticides

“…Cedrene (1) and thujopsene (2) present microbial activity. 9 Additionally, thujopsene shows pesticidal activities against the insect Cullex pipiens pallens, 27 and its autooxidation products show great activity as antifungal or antitermite.…”

“…However, their excessive use have increased pesticide resistance, environmental contamination, and toxicity and affected human health. 1 This problem has led to restrictions on the use of synthetic pesticides being implemented worldwide. 2 One solution lies in developing the use of pesticides of natural origin, known as biopesticides.…”