Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds

doi:10.6023/cjoc202205022

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3870-3879.DOI: 10.6023/cjoc202205022 Previous Articles Next Articles

NOTES

吡啶联噻唑双酰胺类化合物的设计、合成及杀虫活性

陈澍, 邵莹莹, 付欣豪, 陈庆悟, 杜晓华, 谭成侠^*()

浙江工业大学化学工程学院杭州 310014

收稿日期:2022-05-16 修回日期:2022-07-06 发布日期:2022-08-10
通讯作者: 谭成侠
基金资助:
浙江省绿色农药2011协同创新中心开放基金资助项目

Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds

Shu Chen, Yingying Shao, Xinhao Fu, Qingwu Chen, Xiaohua Du, Chengxia Tan()

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2022-05-16 Revised:2022-07-06 Published:2022-08-10
Contact: Chengxia Tan
Supported by:
Project supported by the Collaborative Innovation Center of Zhejiang Province Green Pesticide

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Abstract

Based on the chlorantraniliprole as leading compound, thirty novel pyridyl thiazole diamide compounds using 2-cyanopyridine as the starting material were synthesized through addition, cyclization, substitution, hydrolysis, chlorination, and ammonolysis reactions. The structures of title compounds were characterized by ¹H NMR, ¹³C NMR and HRMS. The bioassay results indicated that at 500 mg/L, compounds IX7, IX12, IX20 and IX26 exhibited 100% insecticidal activities against Mythimna separata, and compound IX20 exhibited 100% insecticidal activity against Spodoptera frugiperda. When the concentration was at 200 mg/L, IX20 exhibited 50% insecticidal activity against Mythimna separata.

Key words: thiazole, diamide, pyridine, insecticidal activity

Cite this article

Shu Chen, Yingying Shao, Xinhao Fu, Qingwu Chen, Xiaohua Du, Chengxia Tan. Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3870-3879.

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References 22

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Compd.	R¹	R²	c/(mg•L^－1)	Mythimna separata	Spodoptera frugiperda
IX1	4-Me	2-Me	500	40	0
IX2	4-Me	3-Me	500	60	0
IX3	4-Me	4-Me	500	30	10
IX4	4-Me	2-F	500	46.7	10
IX5	4-Me	3-F	500	10	0
IX6	4-Me	4-F	500	30	0
IX7	4-Me	2-Cl	500	100	20
IX7	4-Me	2-Cl	200	46.7	—
IX8	4-Me	3-Cl	500	10	0
IX9	4-Me	4-Cl	500	10	10
IX10	4-Me	2,6-Me₂	500	5	0
IX11	4-F	2-Me	500	40	0
IX12	4-F	3-Me	500	100	40
IX12	4-F	3-Me	200	20	—
IX13	4-F	4-Me	500	30	20
IX14	4-F	2-F	500	10	0
IX15	4-F	3-F	500	20	0
IX16	4-F	4-F	500	40	0
IX17	4-F	2-Cl	500	26.7	10
IX18	4-F	3-Cl	500	0	20
IX19	4-F	4-Cl	500	20	0
IX20	4-F	2,6-Me₂	500	100	100
IX20	4-F	2,6-Me₂	200	50	10
IX21	5-F	2-Me	500	0	0
IX22	5-F	3-Me	500	30	0
IX23	5-F	4-Me	500	20	20
IX24	5-F	2-F	500	0	0
IX25	5-F	3-F	500	40	20
IX26	5-F	4-F	500	100	30
IX26	5-F	4-F	200	26.7	—
IX27	5-F	2-Cl	500	30	10
IX28	5-F	3-Cl	500	0	0
IX29	5-F	4-Cl	500	0	0
IX30	5-F	2,6-Me₂	500	0	0
Chlorantraniliprole			500	100	100
Chlorantraniliprole			200	100	100

Compd.	R¹	R²	c/(mg•L^－1)	Mythimna separata	Spodoptera frugiperda
IX1	4-Me	2-Me	500	40	0
IX2	4-Me	3-Me	500	60	0
IX3	4-Me	4-Me	500	30	10
IX4	4-Me	2-F	500	46.7	10
IX5	4-Me	3-F	500	10	0
IX6	4-Me	4-F	500	30	0
IX7	4-Me	2-Cl	500	100	20
IX7	4-Me	2-Cl	200	46.7	—
IX8	4-Me	3-Cl	500	10	0
IX9	4-Me	4-Cl	500	10	10
IX10	4-Me	2,6-Me₂	500	5	0
IX11	4-F	2-Me	500	40	0
IX12	4-F	3-Me	500	100	40
IX12	4-F	3-Me	200	20	—
IX13	4-F	4-Me	500	30	20
IX14	4-F	2-F	500	10	0
IX15	4-F	3-F	500	20	0
IX16	4-F	4-F	500	40	0
IX17	4-F	2-Cl	500	26.7	10
IX18	4-F	3-Cl	500	0	20
IX19	4-F	4-Cl	500	20	0
IX20	4-F	2,6-Me₂	500	100	100
IX20	4-F	2,6-Me₂	200	50	10
IX21	5-F	2-Me	500	0	0
IX22	5-F	3-Me	500	30	0
IX23	5-F	4-Me	500	20	20
IX24	5-F	2-F	500	0	0
IX25	5-F	3-F	500	40	20
IX26	5-F	4-F	500	100	30
IX26	5-F	4-F	200	26.7	—
IX27	5-F	2-Cl	500	30	10
IX28	5-F	3-Cl	500	0	0
IX29	5-F	4-Cl	500	0	0
IX30	5-F	2,6-Me₂	500	0	0
Chlorantraniliprole			500	100	100
Chlorantraniliprole			200	100	100

吡啶联噻唑双酰胺类化合物的设计、合成及杀虫活性

Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds

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