Semisynthesis and insecticidal bioactivities of benzoxazole and benzoxazolone derivatives of honokiol, a naturally occurring neolignan derived from Magnolia officinalis
Semisynthesis and insecticidal bioactivities of benzoxazole and benzoxazolone derivatives of honokiol, a naturally occurring neolignan derived from Magnolia officinalis
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厚朴酚（一种源自厚朴的天然新木脂素）的苯并恶唑和苯并恶唑酮衍生物的半合成和杀虫生物活性
DOI：
10.1016/j.bmcl.2020.127086
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发表时间：
2020
影响因子：
2.7
通讯作者：
Chun Yang
中科院分区：
文献类型：
--
作者：
Xiao-yan Zhi;Ling-yun Jiang;Ting Li;Li-li Song;Yi Wang;Hui Cao;Chun Yang
和厚朴酚是从厚朴和倒卵白玉兰的树皮和叶中分离得到的一种具有天然生物活性的新木脂素，具有许多重要的生物学特性。为了继续发现天然来源的农用化学品，我们合成了37个新的8/8‘-烷基硫醇-苯并恶唑和正烷基苯并恶唑酮类化合物，并测定了它们对粘虫和小菜蛾幼虫的杀虫活性。结果表明，所合成的11个化合物具有较强的杀虫活性。与阳性对照组比较，差异有统计学意义。其中，化合物5h显示出最有希望的杀虫活性。最终死亡率(FMR)为58.6%。同时，化合物7n(FMR=65.3%)、7P(FMR=0.61.5%)和8c(FMR=0.65.3%)显示出较强的杀虫活性。木栓菌素是一种著名的植物性杀虫剂。此外，还讨论了初步的构效关系(SARS)。本研究表明，这些和厚朴酚的衍生物可以作为进一步衍生和开发潜在的植保农药候选化合物的先导。
Honokiol, a natural bioactive neolignan isolated from the bark and leaf ofMagnolia officinalisandMagnolia obovata, exhibits many important biological properties. In continuation of our interest in discovery of the agrochemicals derived from the natural sources, thirty-seven new 8/8′-alkylthiol-benzoxazole andN-alkyl/sulfonyl-benzoxazolone derivatives of honokiol were prepared and their insecticidal activities were evaluated against the larvae ofMythimna separataWalker andPlutella xylostellaLinnaeus. The results showed that eleven derivatives exhibited potent insecticidal activity againstM. separatawhen compared with the positive control. Particularly, compound5hdisplayed the most promising insecticidal activity againstM. separatawith the final mortality rate (FMR) of 58.6%. Meanwhile, compounds7n(FMR = 65.3%),7p(FMR = 61.5%), and8c(FMR = 65.3%) demonstrated a greater insecticidal activity againstP. xylostellathan toosendanin, a well-known botanical insecticide. Additionally, the preliminary structure-activity relationships (SARs) were also discussed. This study indicates that these honokiol derivatives could be used as leads for the further derivation and development of the potential pesticide candidates for crop protection.