Ren Zili, Lv Min, Yang Yanli, Gu Siyan, Li Lulu, Liu Huqi, Xu Hui
College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, China.
School of Marine Sciences, Ningbo University, Ningbo, Zhejiang 315211, China.
J Agric Food Chem. 2025 Jan 22;73(3):1804-1812. doi: 10.1021/acs.jafc.3c08020. Epub 2025 Jan 9.
Recently, the structural optimization of natural bioactive products has been one of the important ways to discover new pesticide candidates. Based on osthole as a lead compound, herein, a series of new 2-isopropanol-4-methoxy-7-alkyl/aryloxycarbonyl-()-vinyl-2,3-dihydrobenzofuran derivatives were synthesized. Steric configurations of compounds , , , , , , and were confirmed by X-ray monocrystallography. Notably, an efficient method for preparation of 2-isopropanol-2,3-dihydrobenzofurans from osthole by the epoxidation and rearrangement reactions was developed. Against Linnaeus, compound ( = CHCHPh; LC: 0.759 mg/mL) displayed a 1.9-fold insecticidal activity compared to that of osthole; against Boisduval, compound ( = (CH)CH; LC: 0.401 mg/mL) exhibited a 3.3-fold acaricidal activity and good control effects compared to those of osthole. By the scanning electron microscope (SEM) imaging method, it was demonstrated that the acaricidal activity of compound may be related to the damage of the cuticle layer crest of . Compound could be further studied as a potential acaricide.
近年来，天然生物活性产物的结构优化一直是发现新农药候选物的重要途径之一。本文以蛇床子素为先导化合物，合成了一系列新型的2-异丙醇-4-甲氧基-7-烷基/芳氧基羰基-（）-乙烯基-2,3-二氢苯并呋喃衍生物。通过X射线单晶衍射确定了化合物、、、、、和的立体构型。值得注意的是，开发了一种通过环氧化和重排反应从蛇床子素制备2-异丙醇-2,3-二氢苯并呋喃的有效方法。对茄二十八星瓢虫，化合物（=CHCHPh；LC：0.759mg/mL）的杀虫活性是蛇床子素的1.9倍；对柑橘全爪螨，化合物（=（CH）CH；LC：0.401mg/mL）的杀螨活性是蛇床子素的3.3倍，且防治效果良好。通过扫描电子显微镜（SEM）成像方法表明，化合物的杀螨活性可能与柑橘全爪螨角质层嵴的损伤有关。化合物可作为一种潜在的杀螨剂作进一步研究。
