Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2062-2069.DOI: 10.6023/cjoc201901009 Previous Articles     Next Articles



丁成荣a,b, 潘亚运a,b, 殷许a, 谭成侠a, 王学东b   

  1. a 浙江工业大学化学工程学院 杭州 310032;
    b 温州医科大学公共卫生与管理学院 浙江省流域水环境与健康风险研究重点实验室 温州 325035
  • 收稿日期:2019-01-07 修回日期:2019-02-27 发布日期:2019-03-29
  • 通讯作者: 谭成侠, 王学东;
  • 基金资助:


Synthesis and Fungicidal Activity of Novel Oxathiapiprolin Derivatives

Ding Chengronga,b, Pan Yayuna,b, Yin Xua, Tan Chengxiaa, Wang Xuedongb   

  1. a College of Chemical Engineering Science, Zhejiang University of Technology, Hangzhou 310032;
    b Zhejiang Provincial Key Laboratory of Watershed Science and Health, College of Public Health and Management, Wenzhou Medical University, Wenzhou 325035
  • Received:2019-01-07 Revised:2019-02-27 Published:2019-03-29
  • Contact: 10.6023/cjoc201901009;
  • Supported by:

    Project supported by the Collaborative Innovation Center of Zhejiang Province Green Pesticide

In order to explore the structure of lead compounds with biological activities, using oxathiapiprolin as a template, sixteen oxathiapiprolin derivatives were designed and synthesized to study the influences of substituent to the fungicidal activities which connected with carbon (No. 5 carbon) near the sulfur on the thiazole ring. All the structures were confirmed by 1H NMR, 13C NMR and HRMS. Preliminary bioassay showed that the target compounds generally had fungicidal activitives in vitro at a concentration of 100 μg/mL, the fungicidal activities of 1-(4-(4-cyclopropyl-5-(2-fluorophenyl)thiazol-2-yl)piperidin- 1-yl)-2-(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)ethan-1-one (9o) against Fusarium graminearum was 60%, the fungicidal activities of six target compounds against Diplocarpon mali were 70%, the fungicidal activities of four target compounds against Phytophthora infestans were 50%, and the fungicidal activities of 2-(5-methyl-3-trifluoromethyl-1H-pyrazol-1- yl)-1-(4-(4-methyl-5-(m-tolyl)thiazol-2-yl)piperidin-1-yl)ethan-1-one (9h) against Botrytis cinerea was 75%. In addtion, the fungicidal activities of the target compounds aganist Diplocarpon mali and Botrytis cinerea at 100 μg/mL were higher to azoxystrobin at 50 μg/mL.

Key words: oxathiapiprolin, thiazole, fungicidal activity