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首页> 美国卫生研究院文献>ACS Omega >Application of Sustainable Natural Bioresources inAgriculture: Iodine-Mediated Oxidative Cyclization for Metal-FreeOne-Pot Synthesis of N-Phenylpyrazole SarisanAnalogues as Insecticidal Agents
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Application of Sustainable Natural Bioresources inAgriculture: Iodine-Mediated Oxidative Cyclization for Metal-FreeOne-Pot Synthesis of N-Phenylpyrazole SarisanAnalogues as Insecticidal Agents

机译：可持续天然生物资源在自然资源中的应用农业：碘介导的无金属氧化环化一锅法合成N-苯基吡唑Sarisan类似物作为杀虫剂

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摘要

In view of potential agricultural activity of sarisan (isolated from many plants or easily synthesized from sesamol, another biorenewable natural product) analogues, many research studies on the application of these biorenewable and abundant natural resources have been proceeded. A series of novel sarisan analogues containing N-phenylpyrazole were synthesized and evaluated for their insecticidal activity against a crop-threatening insect pest, Mythimna separata Walker. Meanwhile, an iodine-mediated oxidative intramolecular C–N bond formation methodology has been established for the one-pot synthesis of these N-phenylpyrazole-containing sarisan analogues. This practical one-pot methodology is metal-free and requires no separation of the less stable intermediate hydrazones. In addition, it was found that compounds >8l–r exhibited more promising insecticidal activity with the final mortality rates (FMRs) >62.1%, when compared with the positive control toosendanin. Especially, compound >8r with 2-fluoro-4-bromophenyl showed the most potent insecticidal activity, the FMR of which was 79.3%. On the basis of this, some interesting results of structure–activity relationships were also discussed.
机译：鉴于莎丽聚糖（从许多植物中分离出来或从另一种生物可再生天然产物芝麻酚中合成而来）的潜在农业活性，已经对这些生物可再生和丰富的自然资源的应用进行了许多研究。合成了一系列含有N-苯基吡唑的新型莎丽珊类似物，并评估了其对威胁农作物的害虫Mythimna separata Walker的杀虫活性。同时，已经建立了碘介导的氧化性分子内C–N键形成方法，用于一锅合成这些含N-苯基吡唑的sarisan类似物。这种实用的一锅法不含金属，不需要分离较不稳定的中间体intermediate。此外，与阳性对照妥森丹宁相比，发现> 8l–r 化合物具有更强的杀虫活性，最终死亡率（FMR）> 62.1％。特别地，具有2-氟-4-溴苯基的化合物> 8r 表现出最强的杀虫活性，其FMR为79.3％。在此基础上，还讨论了结构-活动关系的一些有趣结果。

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