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α-萜品烯酰基农用杀菌活性物的合成及活性研究

Synthesis and Antifungal/Anti-oomycete of Turpentine Based Derivatives

  • 摘要:β-蒎烯为原料,制备3个系列蒎烯基衍生物:二氢枯茗酸酰胺类化合物(5a~5g)、二氢枯茗酸肟酯类化合物(6a~6f)和二氢枯茗酸酰腙类化合物(8a~8f),利用FT-IR、1H NMR、MS对产物结构进行表征。采用菌丝生长速率法探讨了19种化合物的抑菌活性,研究结果表明:19种化合物对苹果腐烂病菌、番茄灰霉病菌和辣椒疫霉均有抑制作用,对苹果腐烂病菌的抑制作用较强,其中化合物5a8e对苹果腐烂病菌的半数有效质量浓度(EC50)达到10.489和10.810 mg/L。通过初步构效关系研究发现:在化合物中引入卤素、氰基和硝基等电负性官能团能显著提高化合物的抑菌活性,其中化合物5a8e可作为先导化合物进一步优化研究。

     

    Abstract: Three pinene-based derivatives of dihydrocuminic amides compounds(5a-5g), dihydrocuminic oxime esters compounds(6a-6f) and dihydrocuminic acyl hydrazones compounds(8a-8f) were prepared from β-pinene. The structurs of the product were characterized by FT-IR, 1H NMR and MS. The bactericidal activities of the obtained compounds were investigated by mycelial growth rate method. The results showed that these 19 compounds had inhibitory effects on Valsa mali, Botrytis cinerea and Phytophthora capsici, where the inhibitory effect on V. mali was stronger. The half effective mass concentration(EC50) values of compounds 5a and 8e against V. mali were 10.489 and 10.810 mg/L, respectively. The results of preliminary structure-activity relationship showed that the introduction of electronegative functional groups such as halogen atoms, cyano groups and nitro groups to the compounds could significantly improve the antibacterial activity of the compounds. Among them, 5a and 8e could be used as lead compounds for further optimization study.

     

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