Citation: Ding Chengrong, Pan Yayun, Yin Xu, Tan Chengxia, Wang Xuedong. Synthesis and Fungicidal Activity of Novel Oxathiapiprolin Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 2062-2069. doi: 10.6023/cjoc201901009 shu

Synthesis and Fungicidal Activity of Novel Oxathiapiprolin Derivatives

Ding Chengrong ^a,b ,
Pan Yayun ^a,b ,
Yin Xu ^a ,
Tan Chengxia ^a,, ,
Wang Xuedong ^b,,

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

Corresponding author: Tan Chengxia, tanchengxia@zjut.edu.cn Wang Xuedong, 1521554541@qq.com
Received Date: 7 January 2019
Revised Date: 27 February 2019
Available Online: 29 July 2019
Fund Project: Project supported by the Collaborative Innovation Center of Zhejiang Province Green Pesticide

Figures(3)

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.
- oxathiapiprolin,
- thiazole,
- fungicidal activity
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