Construction, Pesticidal Activities, Control Effects, and Detoxification Enzyme Activities of Osthole Ester/Amide Derivatives.

Abstract

Pesticide research and development has entered an era of safety, efficiency, and environmental friendliness. Discovery of effective active products directly or indirectly from plant secondary metabolites as pesticide candidates has been one of the current research focuses. Herein, two series of new ester and amide derivatives were prepared by structural modifications of a natural coumarin-type product osthole at its C-4' position. Their structures were characterized by IR, mp, 1H NMR, and HRMS. Confirmation of steric configuration of seven compounds was based on single-crystal analysis. Against Tetranychus cinnabarinus Boisduval (Acari: Tetranychidae), (2'E)-3'-ethoxycarbonylosthole (4b) and (2'E)-3'-(n)hexyloxycarbonylosthole (4e) exhibited 3.2 and 3.1 times acaricidal activity of osthole, and particularly, they also showed 2.4 and 2.2 times control efficiency on the 5th day of osthole. Against Aphis citricola Van der Goot (Homoptera: Aphididae), (2'E)-3'-(p-CF3)benzyloxycarbonylosthole (4w), (2'E)-3'-benzylaminocarbonylosthole (5f), and (2'E)-3'-phenylethylaminocarbonylosthole (5g) showed 1.9-2.1-fold aphicidal activity of osthole. Furthermore, the changes in two detoxification enzyme [carboxylesterase (CarE) and glutathione S-transferase (GST)] activities over time in treated T. cinnabarinus were investigated. These results can pave the foundation for future design and preparation of osthole derivatives as botanical agrochemicals.