5975-50-8Relevant articles and documents
Germacrone derivatives as new insecticidal and acaricidal compounds: A structure-activity relationship
Pretel, Alberto Galisteo,Del Pulgar, Helena Pérez,De León, Estela Guerrero,López-Pérez, José Luis,Olmeda, A. Sonia,Gonzalez-Coloma, Azucena,Barrero, Alejandro F.,Del Moral, José Francisco Quílez
, (2019/08/20)
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.
Biotransformation of germacrane epoxides by Cichorium intybus
Piet, Dennis P.,Schrijvers, Robert,Franssen, Maurice C. R.,De Groot, Aede
, p. 6303 - 6314 (2007/10/02)
The biotransformation of germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3), isogermacrone-4,5-epoxide (5), germacrene B-4,5-epoxide (6) and germacrene B-1,10-epoxide (7) by a suspension of fresh chicory root (Cichorium intybus) was investigated. Enz