为了寻找结构新颖、杀菌活性更好的绿色农药.选用天然产物香草醛作为基本原料,引入五元杂环异唑结构,首次设计并合成了 28 个香草醛异唑类衍生物.结构经核磁共振氢谱、碳谱及高分辨质谱分析确认.测试了所有目标衍生物对烟草灰霉病菌(Botrytis cinerea)、层出镰刀菌(Fusarium proliferatum)、木贼镰刀菌(Fusarium equiseti)、玉米圆斑病菌(Bipolaris zeicola)、胶胞炭疽菌(Colletotrichum gloeosporioides)、草茎点霉菌(Phoma herbarum)6 种广谱菌的杀菌活性.杀菌活性测定结果显示:在 50 μg/mL质量浓度下,部分化合物对 6 种真菌的菌丝生长均具有一定抑制作用,2-甲氧基-4-(5-苯基异唑-3-基)苯乙酸酯对 6 种真菌的抑菌活性整体良好,对玉米圆斑病菌等 3 种菌的抑菌活性超过对照组百菌清;2-甲氧基-4-(5-(4-乙基苯基)异唑-3-基)苯酚对烟草灰霉病菌的抑菌活性最高,抑菌率可以达到 93%.初步构效关系表明,对活性片段香草醛上的酚羟基进行乙酰化衍生,有助于提高化合物对 6 种病原菌的抑菌活性,为后续的生物活性研究提供了参考.
In order to develop green pesticides with novel structure and better antifungal activity.The natural product vanillin was selected as the basic material,and a five-membered isoxazole was introduced into its structure.28 vanillin isoxazole derivatives were designed and synthesized.Their compounds were confirmed by 1 HNMR,13 CNMR and HRMS.Their antifungal activities against Botrytis cinerea,Fusarium proliferatum,Fusarium equiseti,Bipolaris zeicola,Colletotrichum gloeosporioides and Phoma herba-rum were evaluated.The antifungal activity study indicated that at a mass concentration of 50 μg/mL,some compounds had certain inhibitory effects on the mycelial growth of six fungi.The antifungal activity of 2-hydroxy-4-(5-phenylisoxazol-3-yl)phenyl acetate against six fungi was good as a whole.2-hydroxy-4-(5-phenylisoxazol-3-yl)phenyl acetate against three kinds of bacteria,such as Bi-polaris zeicola,was higher than that of the control group chlorothalonil.Moreover,4-(5-(4-ethylphenyl)isoxazol-3-yl)-2-methoxyphe-nol had the highest antifungal activity against Botrytis cinerea,and the antifungal rate can reach 93%.The preliminary structure-activ-ity relationship showed that acetylation and derivatization of phenolic hydroxyl groups on vanillin were helpful to improve the antifun-gal activity of the compound against six fungi,and provided a reference for the subsequent biological activity research.