马鞭草烯酮基磺酸肟酯化合物的合成及抑菌活性

摘要

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,1 H NMR,13 C 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%.%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、1 H NMR、13 C 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%.