有机化学 ›› 2012, Vol. 32 ›› Issue (10): 1951-1957.DOI: 10.6023/cjoc1203162 上一篇    下一篇

研究论文

2-苄砜基-5-甲基-1,2,4-三唑并[1,5-a]嘧啶-7-氧乙酰腙类衍生物的合成及抑菌活性研究

熊启中, 刘军虎, 林选福, 鲍小平   

  1. 贵州大学精细化工研究开发中心 教育部绿色农药与农业生物工程重点实验室 贵阳 550025
  • 收稿日期:2012-03-16 修回日期:2012-05-15 发布日期:2012-06-04
  • 通讯作者: 鲍小平 E-mail:baoxp_1980@yahoo.com.cn
  • 基金资助:

    贵州省优秀科技教育人才省长专项资金(No. 200817)资助项目.

Synthesis and Fungicidal Activities of 2-Benzylsulfonyl-5-methyl- 1,2,4-triazolo[1,5-a]pyrimidine-7-oxoacetohydrazone Derivatives

Xiong Qizhong, Liu Junhu, Lin Xuanfu, Bao Xiaoping   

  1. Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025
  • Received:2012-03-16 Revised:2012-05-15 Published:2012-06-04
  • Supported by:

    Project supported by the Governor’s Foundation for Excellent Talents of Science, Technology & Education of Guizhou Province (No. 200817).

以2-苄硫基-5-甲基-7-羟基-1,2,4-三唑并[1,5-a]嘧啶为起始原料, 设计合成了24个新型的2-苄砜基-5-甲基-1,2,4-三唑并[1,5-a]嘧啶-7-氧乙酰腙类化合物5a5x, 通过1H NMR, IR, MS和元素分析对目标化合物进行了结构表征. 初步生物活性测试结果表明, 在50 μg/mL浓度下, N-[2-苄砜基-5-甲基-1,2,4-三唑并[1,5-a]嘧啶-7-氧乙酰基]-4-甲氧基苯甲醛腙(5k), N-[2-苄砜基-5-甲基-1,2,4-三唑并[1,5-a]嘧啶-7-氧乙酰基]-2-氯-5-硝基苯甲醛腙(5p)和N-[2-苄砜基-5-甲基-1,2,4-三唑并[1,5-a]嘧啶-7-氧乙酰基]-苯丙烯醛腙(5s)对黄瓜灰霉病菌的抑制率均超过70%.

关键词: 1,2,4-三唑并[1,5-a]嘧啶, 砜, 酰腙, 合成, 抑菌活性

Twenty four novel 2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-7-oxoacetohydrazone derivatives 5a5x were synthesized by utilization of 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a] pyrimidine as starting material. All the target compounds were characterized by 1H NMR, IR, MS and elemental analysis. The preliminary bioassay indicated that the inhibition rates of 4-methoxybenzaldehyde N-[2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine]- 7-oxoacetohydrazone (5k), 2-choro-5-nitrobenzaldehyde N-[2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine]-7- oxoacetohydrazone (5p) and cinnamaldehyde N-[2-benzylsulfonyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine]-7-oxoaceto- hydrazone (5s) against Botrytis cinerea reached above 70% at the concentration of 50 μg/mL.

Key words: 1,2,4-triazolo[1,5-a]pyrimidine, sulfone, acetohydrazone, synthesis, fungicidal activity