有机化学 ›› 2017, Vol. 37 ›› Issue (7): 1877-1882.DOI: 10.6023/cjoc201612048 上一篇    下一篇

研究简报

新型2-烷硫基-噻吩并[2,3-d]嘧啶-4-酮衍生物的设计、合成与除草活性

赵安林a, 刘姝a, 朱咏梅b, 王涛a, 罗劲a,b   

  1. a. 江西省化学生物学重点实验室 江西师范大学化学化工学院 南昌 330022;
    b. 江西师范大学分析测试中心 南昌 330022
  • 收稿日期:2019-12-19 修回日期:2017-02-19 发布日期:2017-03-03
  • 通讯作者: 王涛, 罗劲 E-mail:wangtao@jxnu.edu.cn;jinluo@jxnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21262018,21562026)、江西省自然科学基金(Nos.20161BAB203085,20161BAB213072)资助项目.

Designed, Synthesis and Herbicidal Activity of Novel 2-Alkylthio-thieno[2,3-d]pyrimidin-4-ones

Zhao Anlina, Liu Shua, Zhu Yongmeib, Wang Taoa, Luo Jina,b   

  1. a. Jiangxi Province Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022;
    b. Analytical & Testing Center, Jiangxi Normal University, Nanchang 330022
  • Received:2019-12-19 Revised:2017-02-19 Published:2017-03-03
  • Contact: 10.6023/cjoc201612048 E-mail:wangtao@jxnu.edu.cn;jinluo@jxnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos.21262018,21562026) and the Natural Science Foundation of Jiangxi Province (Nos.20161BAB203085,20161BAB213072).

为了寻找具有超高效除草活性的稠杂环化合物,以2-氨基-3-乙氧羰基-5-乙基噻吩为原料设计、合成了16个新型的2-烷硫基-噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物,通过1H NMR、IR、LC-MS和元素分析等测试手段对其结构进行了表征确证.初步对单、双子叶植物的除草活性测试结果表明,部分目标化合物对单、双子叶的根和茎的生长具有很好的抑制作用,其中2-环戊硫基-3-正丙基-6-乙基噻吩并[2,3-d]嘧啶-4-(3H)-酮(4e)和2-正十六烷硫基-3-正丙基-6-乙基噻吩并[2,3-d]嘧啶-4(3H)-酮(4o)在100 mg/L浓度下对单子叶植物稗草根和茎长的抑制率都达到了100%.

关键词: 噻吩并[2,3-d]嘧啶-4(3H)-酮衍生物, 合成, 除草活性

In an attempt to discover novel fuse heterocyclic compound with high herbicidal activity, sixteen newly 2-alkythio-thieno[2,3-d]pyrimidin-4(3H)-ones have been designed and synthesized by the reaction of 3-propyl-6-ethylthieno[2,3-d]pyrimidine-2-thione with halo-hydrocarbon. Their structures were clearly verified by 1H NMR, IR, LC-MS and elemental analysis. Preliminary bioassay results indicate that some target compounds have excellent inhibitory activities on barnyard grass and rape. 2-Cyclopentylthio-3-n-propyl-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one (4e) and 2-n-hexdecylthio-3-n-propyl-6-ethylthieno[2,3-d]pyrimidin-4(3H)-one (4o) show 100% inhibition rate to barnyard grass at the concentration of 100 mg/L.

Key words: thieno[2,3-d]pyrimidin-4(3H)-ones, synthesis, herbicidal activitiess