Huang Xiaobo, Hao Nan, Shu Lili, Wei Zhenyang, Shi Jiawei, Tian Yuee, Chen Genqiang, Yang Xinling, Che Zhiping
College of Horticulture and Plant Protection, Henan University of Science and Technology, Luoyang, China.
Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing, China.
Pest Manag Sci. 2025 Aug;81(8):4243-4255. doi: 10.1002/ps.8785. Epub 2025 Mar 22.
The emergence and increasing intensification of insect pest resistance greatly shortens the service life of commercial insecticides. Hence, the continuous development of novel insecticides is extremely necessary. Discovering new insecticide molecules based on natural products with insecticidal activity has been a popular technique and has made outstanding contributions in this field.
A series of betulin-cinnamic acid-related hybrid compounds was prepared by molecular hybridization through the bridge of acyloxy groups and their chemical structures were unambiguously confirmed. Against A. pisum, compounds 2e, 3a-3e, 3g, 3i, 3j, and 3m showed complete antifeedant activity at 2 mg/mL; compound 5b exhibited 2.7 times the aphicidal activity of the precursor betulin. Against P. xylostella, compound 2l displayed 3.9 times the insecticidal activity of betulin. Meanwhile, some interesting structure-activity relationships were obtained. Furthermore, compound 2l could destroy the ultrastructure of midgut cells and significantly inhibit the activity of α-amylase in P. xylostella larvae. Molecular docking indicated that the lupane skeleton and p-nitrocinnamoyloxy groups played a key role in the binding of compound 2l to α-amylase.
Compounds 5b and 2l could be further optimized structurally as the secondary lead compounds for the discovery of novel insecticide molecules. © 2025 Society of Chemical Industry.
害虫抗药性的出现及不断增强极大地缩短了商业杀虫剂的使用寿命。因此，持续开发新型杀虫剂极为必要。基于具有杀虫活性的天然产物发现新的杀虫剂分子一直是一种流行的技术，并在该领域做出了杰出贡献。
通过酰氧基桥进行分子杂交制备了一系列桦木醇 - 肉桂酸相关的杂化化合物，并明确确认了它们的化学结构。对于豌豆蚜，化合物2e、3a - 3e、3g、3i、3j和3m在2mg/mL时表现出完全的拒食活性；化合物5b的杀蚜活性是前体桦木醇的2.7倍。对于小菜蛾，化合物2l的杀虫活性是桦木醇的3.9倍。同时，获得了一些有趣的构效关系。此外，化合物2l可破坏小菜蛾幼虫中肠细胞的超微结构，并显著抑制其α - 淀粉酶的活性。分子对接表明羽扇豆烷骨架和对硝基肉桂酰氧基在化合物2l与α - 淀粉酶的结合中起关键作用。
化合物5b和2l可在结构上进一步优化，作为发现新型杀虫剂分子的二级先导化合物。© 2025化学工业协会。
