State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China.
Department of Chemistry, School of Science, Tianjin University, Tianjin, 300072, People's Republic of China.
Sci Rep. 2021 Mar 25;11(1):6895. doi: 10.1038/s41598-021-86475-w.
NKY-312 is a highly active insecticide candidate with a simple structure. In order to carry out field trials and toxicity tests, its scale preparation is urgently needed, but the final step of the original synthetic route is a low-yielding sulfonylation reaction that generates a high proportion of a bissulfonylated by-product, its foliar contact activities against bean aphid (80% at 100 mg/kg) is significantly lower than that of NKY-312 (100% at 5 mg/kg), and uses pyridine as the solvent. In this work, we developed a highly selective (4-dimethylaminopyridine)-catalyzed monosulfonylation reaction that avoids the use of pyridine as a solvent and shows a much higher yield (98% yield with 98% HPLC purity) than the original reaction (68%). Then, we carried out the field trials and toxicity tests. In field experiments, the activities of NKY-312 against rice planthopper and wheat aphid were equal to pymetrozine and imidacloprid respectively.
NKY-312 是一种具有简单结构的高效杀虫剂候选物。为了进行田间试验和毒性测试，急需对其进行规模化制备，但原始合成路线的最后一步是产率较低的磺酰化反应，会生成高比例的双磺酰化副产物，其叶面接触活性对豆蚜（100mg/kg 时为 80%）显著低于 NKY-312（5mg/kg 时为 100%），并且使用吡啶作为溶剂。在这项工作中，我们开发了一种高选择性的（4-二甲氨基吡啶）催化单磺酰化反应，避免了使用吡啶作为溶剂，并且比原始反应（68%）具有更高的产率（98%HPLC 纯度下的 98%产率）。然后，我们进行了田间试验和毒性测试。在田间试验中，NKY-312 对稻飞虱和麦蚜的活性分别与吡虫啉和噻虫啉相当。
