RESULTS: Six spatial configurations of 4\'-(p-toluenoyloxy)osthole (4b), 4\'-(m-fluorobenzoyloxy)osthole (4f), 4\'-(p-fluorophenylacetyloxy)osthole (4m), 4\'-(3\'\',4\'\'-methylenedioxybenzoyloxy)osthole (4q), 4\'-formyloxyosthole (4u) and 4\'-acetyloxyosthole (4v) were determined by X-ray mono-crystal diffraction. Compounds 4b, 4\'-(p-chlorobenzoyloxy)osthole (4g), 4\'-(m-chlorobenzoyloxy)osthole (4h), 4\'-(p-bromobenzoyloxy)osthole (4i) and 4\'-(2\'\'-chloropyridin-3\'\'-ylcarbonyloxy)osthole (4p) showed higher insecticidal activity than toosendanin against Mythimna separata Walker; notably, compound 4b displayed 1.8 times insecticidal activity of the precursor osthole. Against Tetranychus cinnabarinus Boisduval, compounds 4g and 4h showed 3.3 and 2.6 times acaricidal activity of osthole, and good control effects in the glasshouse. Scanning electron microscopy assay demonstrated that compound 4g can damage the cuticle layer of T. cinnabarinus resulting in death.
CONCLUSIONS: Compounds 4g and 4h can be further studied as lead pesticidal agents for the management of M. separata and T. cinnabarinus. These results will pave the way for application of osthole derivatives as agrochemicals. © 2024 Society of Chemical Industry.
结果:4'-(对甲苯酰氧基)蛇床子素(4b)的六个空间构型,4'-(间氟苯甲酰基氧基)蛇床子素(4f),4'-(对氟苯基乙酰氧基)蛇床子素(4m),4\'-(3\'\',4\'\'-亚甲二氧基苯甲酰氧基)蛇床子素(4q),通过X射线单晶衍射测定了4'-甲酰基氧基蛇床子素(4u)和4'-乙酰氧基蛇床子素(4v)。化合物4b,4'-(对氯苯甲酰氧基)蛇床子素(4g),4'-(间氯苯甲酰氧基)蛇床子素(4h),4\'-(对溴苯甲酰氧基)蛇床子素(4i)和4\'-(2\''-氯吡啶-3\'''-羰基氧基)蛇床子素(4p)对MythimnaseparataWalker的杀虫活性高于秋葵素;特别是,化合物4b显示的杀虫活性是前体蛇床子素的1.8倍。对朱砂叶猴Boisduval,化合物4g和4h显示蛇床子素的3.3和2.6倍的杀螨活性,和良好的控制效果在温室。扫描电镜分析表明,化合物4g可以破坏朱砂角质层,导致死亡。
结论:化合物4g和4h可以进一步研究作为铅杀虫剂用于分离M.separata和Cinnabarinus的管理。这些结果将为蛇床子素衍生物作为农用化学品的应用铺平道路。©2024化学工业学会。