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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (11): 1918-1924. 上一篇    下一篇

研究论文

2-{2-[3-(取代苯基)-3-氧代-2-1,2,4-三唑-1-基-丙基]-苯基}-2-甲氧亚氨基乙酸甲酯和乙酰甲胺类衍生物的合成与杀菌活性研究

李国华 ; 杨 红*   

  1. (南京农业大学理学院 南京 210095)
  • 收稿日期:2008-02-04 修回日期:2008-05-05 发布日期:2008-11-18
  • 通讯作者: 杨 红

Synthesis and Antifungal Bioactivity of 2-{2-[3-(Subsititued phenyl)- 3-oxo-2-1,2,4-triazol-1-yl-propyl]-phenyl}-[2-methoxyimino]-acetic Acid Methyl Ester and N-Methyl-acetamide Derivatives

LI, Guo-Hua; YANG, Hong*   

  1. (College of Science, Nanjing Agricultural University, Nanjing 210095)
  • Received:2008-02-04 Revised:2008-05-05 Published:2008-11-18
  • Contact: YANG, Hong

PDF

1689

被引次数

24

以2-甲基苯甲酰甲酸甲酯为起始原料, 通过与甲氧基胺的盐酸盐、甲胺、N-溴代丁二酰亚胺(NBS)和1H-1,2,4-三氮唑钠反应合成了两个系列共计22个2-{2-[3-(取代苯基)-3-氧代-2-1,2,4-三唑-1-基-丙基]-苯基}-2-甲氧亚氨基乙酸甲酯和乙酰甲胺类的衍生物. 经IR, 1H NMR和MS对目标化合物进行了结构表征. 用浓度为 10 µg•mL－1的目标化合物进行了初步离体杀菌活性试验, 结果表明: Ha4, Ha5, Ha7对油菜菌核病有杀菌活性; Ha2, Hb8对小麦纹枯病有杀菌活性; Hb4对蔬菜灰霉病有杀菌活性; Hb4, Hb5对小麦赤霉病和小麦纹枯病均有杀菌活性.

关键词: 2-甲氧亚氨基-2-苯基乙酸衍生物, 1H-1,2,4-三氮唑, 杀菌活性, 合成

Twenty-two 2-{2-[3-(subsititued phenyl)-3-oxo-2-1,2,4-triazol-1-yl-propyl]-phenyl}-[2-metho-
xyimino]-acetic acid methyl ester and {2-[3-(subsititued phenyl)-3-oxo-2-1,2,4-triazol-1-yl-propyl]- phenyl}-[2-methoxyimino]-N-methyl-acetamide derivatives were synthesized by reaction of methyl 2-methylbenzoylformate with hydrochloric acid salt of methoxyamine, methylamine, NBS and sodium 1H-1,2,4-triazolyl. The structures of the target compounds were characterized by IR, 1H NMR and mass spectra. These compounds at 10 µg•mL－1 were tested in vitro against five pathogenic fungi, Sclerotonia, Botrytis cinerea Pers, Gibberella zeae, Rhizoctorua solani and Pyricularia oryzae. The compounds Ha4, Ha5 and Ha7 showed potent antifungal activities against Sclerotonia, Ha2 and Hb8 showed potent antifungal ac-tivities against Rhizoctorua solani, Hb4 potent antifungal activities against Botrytis cinerea Pers, Hb4 and Hb5 potent antifungal activities against Gibberella zeae and Rhizoctorua solani.

Key words: 2-methoxyimino-2-phenylacetic acid derivative, synthesis, antifungal activity, 1H-1,2,4-triazole