School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004, Guangxi, P. R. China.
Chem Biodivers. 2021 Jul;18(7):e2100235. doi: 10.1002/cbdv.202100235. Epub 2021 Jun 14.
In search of novel natural product-based bioactive molecules, twenty (ten pairs) novel (Z)-/(E)-anisaldehyde-based oxime ester compounds were designed and synthesized by using anisaldehyde as starting material. Structural characterization of the target compounds was carried out by NMR, FT-IR, ESI-MS, and elemental analysis. Their herbicidal and antifungal activities were preliminarily tested. As a result, at 50 μg/mL, compound (E)-5b exhibited excellent to good inhibition rates of 92.3 %, 79.2 %, and 73.9 %, against Rhizoctonia solani, Fusarium oxysporum f. sp. cucumerinum, and Bipolaris maydis, respectively, better than or comparable to that of the positive control chlorothalonil. In addition, at 100 μg/mL, compounds (E)-5b, (E)-5f, (Z)-5f and (E)-5d exhibited excellent to good inhibition rates of 85.8 %, 82.9 %, 78.6 % and 64.2 %, respectively, against the root-growth of rape (B. campestris), much better than that of the positive control flumioxazin. The bioassay result also showed that the synthesized compounds had obvious differences in antifungal and herbicidal activities between (Z)- and (E)-isomers. Preliminary structure-activity relationship was also discussed by theoretical calculation.
为了寻找新型天然产物生物活性分子，我们以香草醛为起始原料，设计并合成了二十种（十种对映异构体）新型（Z）-/（E）-苯甲醛肟酯化合物。通过 NMR、FT-IR、ESI-MS 和元素分析对目标化合物进行了结构表征。初步测试了它们的除草和杀菌活性。结果表明，在 50μg/mL 时，化合物（E）-5b 对茄丝核菌、黄瓜枯萎病菌和玉米弯孢叶斑病菌的抑制率分别达到 92.3%、79.2%和 73.9%，优于或与阳性对照药剂百菌清相当。此外，在 100μg/mL 时，化合物（E）-5b、（E）-5f、（Z）-5f 和（E）-5d 对油菜根生长的抑制率分别达到 85.8%、82.9%、78.6%和 64.2%，明显优于阳性对照药剂氟噻草胺。生物测定结果还表明，所合成的化合物在杀菌和除草活性方面，（Z）-和（E）-异构体之间存在明显差异。还通过理论计算初步探讨了构效关系。
