Citation: He Wenjing, Liu Denyue, Gan Xiuhai, Zhang Jian, Liu Zhengjun, Yi Chongfen, Song Bao'an. Synthesis and Biological Activity of Novel 1, 3, 4-Thiadiazolo[3, 2-a]pyrimidinone Mesoionic Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2287-2294. doi: 10.6023/cjoc201903023 shu

Synthesis and Biological Activity of Novel 1, 3, 4-Thiadiazolo[3, 2-a]pyrimidinone Mesoionic Derivatives

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Corresponding author: Song Bao'an, songbaoan22@yahoo.com
Received Date: 13 March 2019
Revised Date: 5 April 2019
Available Online: 16 August 2019
Fund Project: the National Key Research and Development Program of China 2018YFD0200100Project supported by the National Key Research and Development Program of China (No. 2018YFD0200100)

Figures(2)

A series of 1, 3, 4-thiadiazolo[3, 2-a]pyrimidinone mesoionic derivatives were designed and synthesized with triflumezopyrim as the leading compound, and their structures were characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. The preliminary biological activities indicated that the target compounds showed certain insecticidal activities at 100 μg/mL, of which the lethality rates of 2-((4-chlorobenzyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phen-yl)-5H-[1, 3, 4]-thiadiazolo[3, 2-a]pyrimidin-8-ium-7-olate (8b) and 2-(((2-chlorothiazol-5-yl)methyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phenyl)-5H-[1, 3, 4]thiadiazolo-[3, 2-a]pyrimidin-8-ium-7-olate (8d) against white-backed planthopper (WBPH) were 70%. Some compounds showed good antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas citri pv. citri (Xcc) at 50 μg/mL, and the inhi-bitory rates of 2-((2-(trifluoromethyl)benzyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phenyl)-5H-[1, 3, 4]thiadiazolo[3, 2-a]pyrimidin-8-ium-7-olate (8h) to Xoo and Xoc were 70.91% and 53.34%, respectively, which were better than thiodiazole copper (47.76% and 23.25%) and bismerthiazol (66.97% and 17.24%). The inhibition rate of 2-((3-(tri-fluoromethyl)benzyl)thio)-8-((2-chlorothiazol-5-yl)methyl)-5-oxo-6-(3-(trifluoromethyl)phenyl)-5H-[1, 3, 4]thiadiazolo[3, 2-a]-pyrimidin-8-ium-7-olate (8e) to Xcc was 68.97%, which was better than thiediazole copper (35.85%) and bismerthiazol (37.53%)
- mesoionic,
- 1, 3, 4-thiadiazolo[3, 2-a]pyrimidinone,
- insecticidal activity,
- antibacterial activity
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