Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2091-2098.DOI: 10.6023/cjoc202012006 Previous Articles     Next Articles



刘航1, 张舒昀1, 李欢1, 张燕1, 李正名1, 王宝雷1,*()   

  1. 1 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2020-12-01 修回日期:2020-12-31 发布日期:2021-02-22
  • 通讯作者: 王宝雷
  • 基金资助:
    国家自然科学基金(21772103); 国家自然科学基金(22077070)

Synthesis and Biological Activities of Novel 8-((3,4,4-Trifluorobut-3-en-1-yl)thio)-substituted Methylxanthines and Their Derivatives

Hang Liu1, Shuyun Zhang1, Huan Li1, Yan Zhang1, Zhengming Li1, Baolei Wang1,*()   

  1. 1 State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
  • Received:2020-12-01 Revised:2020-12-31 Published:2021-02-22
  • Contact: Baolei Wang
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(21772103); National Natural Science Foundation of China(22077070)

Using 8-chlorotheophylline and 4-bromo-1,1,2-trifluorobut-1-ene as materials, a series of novel 8-((3,4,4-tri- fluorobut-3-en-1-yl)thio)-substituted methylxanthines and their derivatives were successfully synthesized through nucleophilic substitution, protection, deprotection, and oxidation. The structures of the title compounds were confirmed and characterized by melting point, 1H NMR, 13C NMR, 19F NMR and HRMS. Their preliminary bioassay results showed that most of the compounds in this series have good insecticidal activity. Among them, 1,3,7-trimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)thio)- 3,7-dihydro-1H-purine-2,6-dione (5a), 7-isobutyl-1,3-dimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)thio)-3,7-dihydro-1H-purine- 2,6-dione (5c) and 7-isobutyl-1,3-dimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-3,7-dihydro-1H-purine-2,6-dione (5h) had 70% lethality rate against Mythimna separata Walker at a concentration of 200 mg?L–1. 5a, 5c and 1,3,7-trimethyl- 8-((3,4,4-trifluorobut-3-en-1-yl)sulfonyl)-3,7-dihydro-1H-purine-2,6-dione (5f) exhibited lethality rates of 72%, 80% and 65% against Plutella xylostellaL. at a concentration of 10 mg?L–1, respectively. Some of the compounds also showed certain fungicidal activity at 50 mg?L–1, among which 7-(cyclopropylmethyl)-1,3-dimethyl-8-((3,4,4-trifluorobut-3-en-1-yl)thio)-3,7- dihydro-1H-purine-2,6-dione (5b) possessed inhibition rates of 66.7% and 61.1% against Phytophthora capsici and Botrytis cinerea, respectively. 5c held a 55.6% inhibition rate towards Botrytis cinerea. This type of compounds provides new lead structures for the further research and development of novel insecticides.

Key words: 8-substituted methylxanthine derivative, synthesis, insecticidal activity, fungicidal activity, structure-activity relationship