马鞭草烯酮基噻唑-腙化合物的合成及抑菌活性

本文合成了9个马鞭草烯酮基噻唑-腙化合物4a～4i(包括3对E-Z异构体和3个E-型产物),采用FTIR、¹H NMR、¹³C NMR、ESI-MS和NOESY对其进行了结构表征,并测试了目标化合物的抑菌活性。结果表明,在质量浓度为50mg/L时,化合物4a～4i对苹果轮纹病菌、小麦赤霉病菌、黄瓜枯萎病菌、花生褐斑病菌、番茄早疫病菌、水稻纹枯病菌、玉米小斑病菌和西瓜炭疽病菌均有一定的抑菌活性。E-Z异构体对一些植物病原菌的抑制作用有明显差异,例如,(Z)-马鞭草烯酮基对-氰基苯基噻唑-腙(4f)对小麦赤霉病菌的抑制率是(E)-马鞭草烯酮基对-氰基苯基噻唑-腙(4e)的6倍。利用Gaussian 09计算了化合物4e和4f的前线分子轨道。

Syntheses and Antifungal Activities of Verbenone-Based Thiazole-hydrazone Compounds

In this paper, nine verbenone-based thiazole-hydrazone compounds 4a~4i, including three pairs of E-Z isomers and three E-products were synthesized. All the target compounds were characterized by FTIR, ¹H NMR, ¹³C NMR, ESI-MS, and NOESY, and their antifungal activities were evaluated as well. The results showed that, at 50mg/L, compounds 4a~4i showed certain antifungal activities against Physalospora piricola, Gibberella zeae, Fusarium oxysporum f. cucumerinum, Cercospora arachidicola, Alternaria solani, Rhizoctonia solani, Helminthosporium maydis, and Colleetotrichum lagenarium. It was found that the E-Z isomers exhibited obvious difference in antifungal activity against some pathogens. For example, the inhibition rate of (Z)-verbenone-based p-cyanophenyl thiazole-hydrazone (4f) against Gibberella zeae was 6 times that of (E)-verbenone-based p-cyanophenyl thiazole-hydrazone (4e). The frontier molecular orbitals of compounds 4e and 4f were calculated by Gaussian 09 software.