State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, No. 94, Weijin Road, Nankai District, Tianjin, 300071, People's Republic of China.
Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, People's Republic of China.
Mol Divers. 2023 Apr;27(2):571-588. doi: 10.1007/s11030-022-10402-y. Epub 2022 Jun 6.
To search a novel lead structure for antiphytopathogenic fungus agent, a series of novel psoralen derivatives possessing sulfonohydrazide or acylthiourea structure were designed and synthesized, and their fungicidal activity against seven phytopathogens was evaluated. Their structures were confirmed by melting points, H NMR, C NMR and HRMS, and the typical crystal structure was determined by X-ray diffraction for validation. Preliminary fungicidal activity showed that some of the title compounds exhibited certain-to-high fungicidal activity. Compound I-13 exhibited good fungicidal activity against Botrytis cinerea, Cercospora arachidicola and Physalospora piricola with EC values of 12.49, 13.22 and 12.12 μg/mL, respectively. Compounds II-9 and II-15 showed over 90% inhibition against B. cinerea at 50 μg/mL in vitro. In particular, II-9 exhibited significant higher fungicidal activity with a lower EC value of 9.09 μg/mL than the positive control YZK-C22 (13.41 μg/mL). Our studies found that sulfonohydrazide or acylthiourea-containing psoralen derivatives were promising fungicide leads deserve for further study.
为了寻找抗植物病原真菌的新型先导结构，设计并合成了一系列具有磺酰肼基或硫代脲基结构的新型补骨脂素衍生物，并评价了它们对 7 种植物病原菌的杀菌活性。通过熔点、氢核磁共振谱（H NMR）、碳核磁共振谱（C NMR）和高分辨质谱（HRMS）确定了它们的结构，并通过 X 射线衍射确定了典型晶体结构以验证。初步杀菌活性表明，部分标题化合物表现出一定程度到高的杀菌活性。化合物 I-13 对灰葡萄孢、花生褐斑病菌和梨叶点霉表现出良好的杀菌活性，EC50 值分别为 12.49、13.22 和 12.12μg/mL。化合物 II-9 和 II-15 在 50μg/mL 时对灰葡萄孢的抑制率超过 90%。特别是，化合物 II-9 表现出显著更高的杀菌活性，其 EC50 值为 9.09μg/mL，低于阳性对照药 YZK-C22（13.41μg/mL）。我们的研究发现，含有磺酰肼基或硫代脲基的补骨脂素衍生物是很有前途的杀菌剂先导化合物，值得进一步研究。
