吡啶联噻唑双酰胺类化合物的设计、合成及杀虫活性

doi:10.6023/cjoc202205022

摘要/Abstract

以氯虫苯甲酰胺作为先导化合物, 2-氰基吡啶作为起始原料, 经加成、环合、取代、水解、氯化和胺解反应, 设计合成了30个新型的吡啶联噻唑双酰胺类化合物, 其结构经¹H NMR、¹³C NMR和高分辨质谱进行表征. 初步杀虫活性测试结果显示, 在浓度为500 mg/L条件下, IX7、IX12、IX20以及IX26对粘虫(Mythimna separata)的杀虫活性为100%, 另外, IX20在500 mg/L时对草地贪夜蛾(Spodoptera frugiperda)的杀虫活性也为100%. 当浓度为200 mg/L时,IX20对粘虫的杀虫活性为50%.

关键词: 噻唑, 双酰胺类, 吡啶, 杀虫活性

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

引用此文

陈澍, 邵莹莹, 付欣豪, 陈庆悟, 杜晓华, 谭成侠. 吡啶联噻唑双酰胺类化合物的设计、合成及杀虫活性[J]. 有机化学, 2022, 42(11): 3870-3879.

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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参考文献 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