High Value-Added
Application
of Natural Plant Products in Crop Protection: Construction and Pesticidal
Activities of Piperine-Type Ester Derivatives and Their Toxicology
Study
posted on 2022-12-16, 21:11authored byTianze Li, Min Lv, Houpeng Wen, Jingru Wang, Zhen Wang, Jianwei Xu, Shanshan Fang, Hui Xu
To discover new potential pesticide
candidates, recently,
structural
modification of natural bioactive products has received much attention.
In this work, a series of new piperine-type ester derivatives were
regio- and stereoselectively synthesized based on a natural alkaloid
piperine isolated from Piper nigrum. Their structures were characterized by IR, mp, 1H NMR
(13C NMR), and high-resolution mass spectrometry (HRMS).
Against Tetranychus cinnabarinus Boisduval
(Acari: Tetranychidae), compounds 4e, 4f, 4u, and 4v displayed the most significant
acaricidal activity with LC50 values of 0.155, 0.117, 0.177,
and 0.164 mg/mL, respectively. Particularly, compound 4f showed >120-fold higher acaricidal activity than piperine (LC50: 14.198 mg/mL). Notably, the acaricidal activity of 4f was equivalent to that of the commercial acaricide spirodiclofen
(LC50: 0.115 mg/mL). Additionally, against Eriosoma lanigerum Hausmann (Hemiptera: Aphididae),
compounds 4w and 4b′ showed 1.8-fold
aphicidal activity of piperine. Furthermore, via the
scanning electron microscope (SEM) imaging method, the obvious destruction
of the construction of the cuticle layer of 4f-treated T. cinnabarinus was observed. Compound 4f could be further studied as a lead acaricidal agent.