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

doi:10.6023/cjoc201903023

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2287-2294.DOI: 10.6023/cjoc201903023 Previous Articles Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

新型1,3,4-噻二唑并[3,2-a]嘧啶酮类介离子衍生物的合成及其生物活性

何文静, 刘登曰, 甘秀海, 张建, 刘峥军, 易崇粉, 宋宝安

贵州大学绿色农药与农业生物工程国家重点实验室培育基地/教育部绿色农药与生物工程重点实验室/精细化工研究开发中心贵阳 55002

收稿日期:2019-03-13 修回日期:2019-04-05 发布日期:2019-04-16
通讯作者: 宋宝安 E-mail:songbaoan22@yahoo.com
基金资助:
国家重点研发计划（No.2018YFD0200100）资助项目.

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

He Wenjing, Liu Denyue, Gan Xiuhai, Zhang Jian, Liu Zhengjun, Yi Chongfen, Song Bao'an

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

Received:2019-03-13 Revised:2019-04-05 Published:2019-04-16
Contact: 10.6023/cjoc201903023 E-mail:songbaoan22@yahoo.com
Supported by:
Project supported by the National Key Research and Development Program of China (No. 2018YFD0200100).

1. Synthesis and Biological Activity of Novel 1,3,4-Thiadiazolo[3,2-a]pyrimidinone Mesoionic Derivatives.PDF(2063KB)

Abstract

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%)

Key words: mesoionic, 1,3,4-thiadiazolo[3,2-a]pyrimidinone, insecticidal activity, antibacterial activity

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(8): 2287-2294.

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新型1,3,4-噻二唑并[3,2-a]嘧啶酮类介离子衍生物的合成及其生物活性

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

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