马鞭草烯酮基磺酸肟酯化合物的合成及抑菌活性

doi:10.3969/j.issn.0253-2417.2017.05.009

林产化学与工业 ›› 2017, Vol. 37 ›› Issue (5): 68-78.doi: 10.3969/j.issn.0253-2417.2017.05.009

马鞭草烯酮基磺酸肟酯化合物的合成及抑菌活性

张瑞¹, 段文贵¹, 林桂汕¹, 陈智聪¹, 何冉¹, 雷福厚²

1. 广西大学化学化工学院, 广西南宁 530004;
2. 广西林产化学与工程重点实验室, 广西南宁 530008

收稿日期:2017-03-13 出版日期:2017-10-25 发布日期:2017-10-30
通讯作者: 段文贵,教授,博士生导师,主要从事天然资源化学和有机合成研究;E-mail:wgduan@gxu.edu.cn。 E-mail:wgduan@gxu.edu.cn
作者简介:张瑞(1989-),男,陕西咸阳人,硕士生,从事天然产物改性及有机合成研究
基金资助:
国家自然科学基金资助项目（31560194）；广西林产化学与工程重点实验室开放基金资助项目（GXFC14-01）；广西大学“大学生创新创业训练计划”资助项目（201610593170）

Synthesis and Antifungal Activity of Verbenone-based Oxime Sulfonate Compounds

ZHANG Rui¹, DUAN Wengui¹, LIN Guishan¹, CHEN Zhicong¹, HE Ran¹, LEI Fuhou²

1. College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
2. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, China

Received:2017-03-13 Online:2017-10-25 Published:2017-10-30

摘要/Abstract

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%。

关键词: α-蒎烯, 马鞭草烯酮, 磺酸肟酯, 合成, 抑菌活性

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%。

Key words: α-pinene, verbenone, oxime sulfonate, synthesis, antifungal activity

中图分类号:

TQ351

张瑞, 段文贵, 林桂汕, 陈智聪, 何冉, 雷福厚. 马鞭草烯酮基磺酸肟酯化合物的合成及抑菌活性[J]. 林产化学与工业, 2017, 37(5): 68-78.

ZHANG Rui, DUAN Wengui, LIN Guishan, CHEN Zhicong, HE Ran, LEI Fuhou. Synthesis and Antifungal Activity of Verbenone-based Oxime Sulfonate Compounds[J]. Chemistry and Industry of Forest Products, 2017, 37(5): 68-78.

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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

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