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马鞭草烯酮基磺酸肟酯化合物的合成及抑菌活性

Synthesis and Antifungal Activity of Verbenone-based Oxime Sulfonate Compounds

  • 摘要: 以α-蒎烯为原料,先将α-蒎烯选择性氧化制备马鞭草烯酮,再经羰基的肟化和O-磺酰化反应,合成得到22个未见文献报道的马鞭草烯酮基磺酸肟酯化合物( 4a ~ 4v )。通过FT-IR、1H NMR、13C NMR和ESI-MS对化合物结构进行了分析和表征,并测试了目标化合物的抑菌活性。抑菌活性测试表明,在质量浓度50 mg/L时,目标化合物对8种供试病菌有一定的抑制活性,其中目标化合物马鞭草烯酮基正丁基磺酸肟酯( 4u )对水稻纹枯病菌(Rhizoctonia solani)的抑菌率达83.2%,化合物马鞭草烯酮基2,4-二氟苯磺酸肟酯( 4d )对小麦赤霉病菌(Fusarium graminearum)的抑菌率达89.6%(优于阳性对照百菌清),化合物马鞭草烯酮基对-硝基苯磺酸肟酯( 4n )和 4u 对花生褐斑病菌(Cercospora arachidicola)的抑菌率均为72.5%。

     

    Abstract: Verbenone was prepared by the selective oxidation of α-pinene at first. Then, twenty-two novel verbenone-based oxime sulfonate compounds( 4a - 4v )were synthesized by the oximation and O-sulfonylation reaction of the carbonyl group in verbenone. The target compounds were analyzed and characterized by FT-IR,1H NMR,13C NMR, and ESI-MS. Antifungal activity test showed that, at the mass concentration of 50 mg/L, the target compounds exhibited certain inhibition activity against the eight tested fungi. Inhibition rate of verbenone-based n-butyl oxime sulfonate( 4u ,R=(CH2)3CH3) against Rhizoctonia solani was 83.2%,inhibition rate of verbenone-based 2,4-difluorophenyl oxime sulfonate( 4d ,R=2,4-FPh) against Fusarium graminearum was 89.6% (better than the positive control chlorothalonil),and inhibition rate of verbenone-based p-nitrophenyl oxime sulfonate( 4n ,R=p-NO2Ph)and 4u (R=(CH2)3CH3) against Cercospora arachidicola was 72.5%。

     

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