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林产化学与工业 ›› 2017, Vol. 37 ›› Issue (1): 54-62.doi: 10.3969/j.issn.0253-2417.2017.01.007

• 研究报告 • 上一篇    下一篇

紫苏醛基席夫碱-(硫)脲化合物的合成及生物活性

马媛1, 段文贵1, 林桂汕1, 刘陆智1, 黄正松1, 雷福厚2   

  1. 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:2016-04-05 出版日期:2017-02-25 发布日期:2017-02-25
  • 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的研究;E-mail:wgduan@gxu.edu.cn。 E-mail:wgduan@gxu.edu.cn
  • 作者简介:马媛(1990-),女,宁夏中卫人,硕士生,从事天然产物改性及有机合成的研究
  • 基金资助:
    国家自然科学基金资助项目(31460173);广西林产化学与工程重点实验室开放基金资助项目(GXFC15-01);广西大学“大学生创新创业训练计划”资助项目(201510593002)

Synthesis and Biological Activities of Perillaldehyde-based Schiff Base-(thio) urea Compounds

MA Yuan1, DUAN Wengui1, LIN Guishan1, LIU Luzhi1, HUANG Zhengsong1, LEI Fuhou2   

  1. 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:2016-04-05 Online:2017-02-25 Published:2017-02-25

摘要: 以紫苏醛为原料,设计合成了13个未见文献报道的紫苏醛基席夫碱-(硫)脲化合物(5a~5m),通过FT-IR、1H NMR、13C NMR和ESI-MS对其结构进行了分析和表征,并测试了目标化合物的抑菌和除草活性。生物活性测试表明,在质量浓度50 mg/L下,目标化合物5f(R=p-FAr)对苹果轮纹病菌的抑制率达90.0%(接近阳性对照嘧菌酯),化合物5d(R=Ar)对番茄早疫病菌的抑制率达91.8%(接近阳性对照嘧菌酯)。在质量浓度100 mg/L下,目标化合物5c(R=环己基)、5i(R=p-CH3Ar)和5a(R=CH3)对油菜胚根生长的抑制率分别为77.6%、75.3%和67.4%(高于阳性对照丙炔氟草胺)。总体上,取代苯基硫脲类目标化合物的抑菌和除草活性优于取代苯基脲类目标化合物。

关键词: 紫苏醛, 席夫碱-(硫)脲, 合成, 抑菌活性, 除草活性

Abstract: Thirteen novel perillaldehyde-based Schiff base-(thio)urea compounds (5a-5m) were designed and synthesized by using perillaldehyde as starting material. Their structures were analyzed and characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS. The results of preliminary bioassay showed that, at the mass concentration of 50 mg/L, the inhibition rate of target compound 5f (R=p-FAr) against Physalospora piricola was 90.0% (close to that of the positive control azoxystrobin), and the inhibition rate of target compound 5d (R=Ar) against Alternaria solani was 91.8% (close to that of the positive control azoxystrobin). Besides, at the mass concentration of 100 mg/L, the target compounds 5c (R=cyclopentyl), 5i (R=p-CH3Ar) and 5a (R=CH3) exhibited 77.6%, 75.3% and 67.4% inhibition against the growth of rape (Brassica campestris) root, respectively (greater than positive control flumioxazin). Furthermore, substituted phenyl thioureas showed better antifungal and herbicidal activities than substituted phenyl ureas.

Key words: perillaldehyde, Schiff base-(thio)urea, synthesis, antifungal activity, herbicidal activity

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