Optimization of Osthole in the Lactone Ring as an Agrochemical Candidate: Synthesis, Characterization, and Pesticidal Activities of Osthole Amide/Ester Derivatives and Their Effects on Morphological Changes of Mite Epidermis

Abstract

Structural modification of natural products is one of the important ways in the discovery of novel pesticides. Based on a diversity-oriented synthesis strategy, herein, two series of amide/ester derivatives (52 compounds) were obtained by opening the lactone of osthole. Interestingly, the effect of different concentrations of aq. sodium hydroxide on the ratio of two isomers ( cis - and trans -2 ) was investigated, and a magical phenomenon of ultraviolet (UV) light irradiation on intertransformation of two isomers ( cis - and trans -2 ) was observed. Against Mythimna separata, when compared with the precursor osthole, compounds 4b, 4l, 5l, 5m, 7h, 7l, and 7m displayed more pronounced growth inhibitory activity with the final mortality rates of 62.0–68.9%. Compounds 4b, 4i, and 5m showed 5.7–6.6 times stronger acaricidal activity against Tetranychus cinnabarinus than osthole, and notably, control effects of compounds 4i and 5m were 2.4- and 2.7-fold that of osthole in the management of T. cinnabarinus in the greenhouse. Scanning electron microscopy (SEM) images of the epidermis of 5m- treated T. cinnabarinus indicated that compound 5m can destroy the mite cuticle layer. Compounds 4b and 5m can be used as leads to further explore more promising pesticidal agents.