Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

doi:10.6023/cjoc202102017

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3633-3642.DOI: 10.6023/cjoc202102017 Previous Articles Next Articles

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含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺衍生物的合成及生物活性

代阿丽, 张仁凤, 李传会, 余利娇, 王娅, 吴剑^*()

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农业生物工程重点实验室贵阳 550025

收稿日期:2021-02-03 修回日期:2021-04-30 发布日期:2021-06-29
通讯作者: 吴剑
基金资助:
国家自然科学基金(21762012); 国家自然科学基金(32072445); 国家自然科学基金(21562012); 高等学校学科创新引智计划计划(D20023(111计划)); 高等学校学科创新引智计划计划(D20023(D20023)); 贵州省科技技术基金(黔科合[2017]1402); 贵州省科技技术基金(黔科合[2017]5788)

Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu()

State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025

Received:2021-02-03 Revised:2021-04-30 Published:2021-06-29
Contact: Jian Wu
Supported by:
National Natural Science Foundation of China(21762012); National Natural Science Foundation of China(32072445); National Natural Science Foundation of China(21562012); Program of Introducing Talents to Chinese Universities (111 Program(D20023(D20023)); S &T Planning Project of Guizhou Province(黔科合[2017]1402); S &T Planning Project of Guizhou Province(黔科合[2017]5788)

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Abstract

A series of novel N-cyano sulfonyimide derivatives containing trifluoromethyl pyridinamide were designed and synthesized by combination method of active substructure, and their structures were identified by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. Their antibacterial activity against Xanthomonas axonopodis pv. citri (Xac), Ralstonia solanacearum (R solanacearum), Xanthomonas oryzae pv. oryzae (Xoo) and insecticidal activity on Plutella xylostella (P. xylostella) were investigated. Some of the compounds were tested to display good antibacterial and moderate insecticidal activities. Among them, 3-chloro-N-(2-(N-cyano-S-(3,4-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G10) showed 67%, 53% and 48% activities against Xac, R. Solanacearum and Xoo at 200 mg/L, respectively. The antibacterial activity of 3-chloro-N- (2-(N-cyano-S-(2,5-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G17) against Xac was 69% and the inhibition rate of N-(2-(S-(2-bromo-4-fluorobenzyl)-N-cyanosulfonimidoyl)ethyl)-3-chloro-5-(trifluoromethyl)picolinamide (G14) on Xoo was 49%. N-(2-(S-(4-Bromo-2-fluorobenzyl)-N-cyanosulfonimidoyl)ethyl)-3-chloro-5-(trifluoromethyl)picolinamide (G1), 3-chloro-N-(2-(N-cyano-S-(3-fluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G7), 3-chloro- N-(2-(N-cyano-S-(2,4-difluorobenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G8) and G10 also had moderate bactericidal activity at 100 mg/L, which are slightly higher than or comparable to that of the positive controls at the corresponding concentration. Moreover, compounds G10 and 3-chloro-N-(2-(N-cyano-S-(4-isopropylbenzyl)sulfonimidoyl)ethyl)-5-(trifluoromethyl)picolinamide (G11) also showed moderate insecticidal activity against P. xvlostella of 77% and 70% at 500 mg/L.

Key words: trifluoromethylpyridine, N-cyano sulfonimide, synthesis, antibacterial activity, insecticidal activity

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Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu. Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3633-3642.

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References 42

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Compd.	Xac		R. solanacearum		Xoo
Compd.	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL
G1	49.26±3.73	48.55±2.35	43.21±4.11	41.72±1.57	47.41±4.49	39.09±4.56
G2	36.38±1.62	35.95±3.10	49.74±0.51	33.90±3.35	29.46±2.95	24.12±1.15
G3	33.97±1.39	31.07±0.99	46.76±2.76	34.90±3.68	17.58±3.95	0.63±1.51
G4	34.68±2.55	31.85±1.10	35.56±0.21	34.98±2.40	12.14±2.78	7.74±2.78
G5	40.06±2.44	34.75±2.41	33.28±3.76	32.32±0.95	16.64±0.75	3.98±0.75
G6	36.66±2.86	31.28±1.32	39.38±4.56	36.41±2.57	0.94±3.81	0.31±3.87
G7	51.88±4.59	42.60±1.12	51.01±3.30	38.73±2.33	15.70±4.16	1.62±5.00
G8	34.32±1.68	32.27±1.84	52.39±1.65	37.98±2.89	7.80±3.87	5.18±2.97
G9	36.02±1.48	31.78±0.45	45.06±2.25	24.20±4.88	14.55±3.25	10.36±3.54
G10	67.30±2.36	46.99±3.93	53.18±1.51	36.82±0.75	48.92±3.60	31.87±1.92
G11	59.94±2.42	46.19±4.16	36.52±1.80	35.14±2.55	19.94±4.73	5.86±4.26
G12	42.96±1.04	36.73±0.44	42.73±1.03	32.30±0.78	9.84±3.29	4.87±3.47
G13	40.62±1.03	36.23±2.66	29.09±2.40	27.65±3.04	25.54±4.29	24.96±1.47
G14	35.31±2.45	23.21±1.75	31.58±2.36	29.99±0.70	49.55±2.40	12.72±3.20
G15	35.78±2.25	32.77±3.36	45.59±3.21	28.75±1.99	28.57±4.05	24.39±2.36
G16	49.04±2.26	27.25±3.23	42.36±2.69	32.60±0.15	17.63±4.31	4.55±2.71
G17	69.14±4.77	38.36±1.38	45.70±3.80	19.90±0.52	22.45±1.41	19.31±3.60
G18	32.91±1.45	32.34±2.16	37.69±4.10	26.52±2.49	22.08±1.45	27.26±0.38
G19	47.56±1.65	30.36±3.61	35.51±1.39	26.11±4.35	38.88±1.91	36.42±3.56
G20	48.90±2.72	32.84±0.93	43.52±1.68	31.85±0.17	23.39±3.70	14.91±4.72
噻唑锌	75.30±1.62	58.21±2.34	52.30±1.15	35.90±2.65	68.23±1.28	50.36±3.17
中生菌素	52.32±2.38	43.31±1.68	51.20±3.02	33.52±2.19	65.35±3.12	46.53±2.82

Compd.	Xac		R. solanacearum		Xoo
Compd.	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL	200 μg/mL	100 μg/mL
G1	49.26±3.73	48.55±2.35	43.21±4.11	41.72±1.57	47.41±4.49	39.09±4.56
G2	36.38±1.62	35.95±3.10	49.74±0.51	33.90±3.35	29.46±2.95	24.12±1.15
G3	33.97±1.39	31.07±0.99	46.76±2.76	34.90±3.68	17.58±3.95	0.63±1.51
G4	34.68±2.55	31.85±1.10	35.56±0.21	34.98±2.40	12.14±2.78	7.74±2.78
G5	40.06±2.44	34.75±2.41	33.28±3.76	32.32±0.95	16.64±0.75	3.98±0.75
G6	36.66±2.86	31.28±1.32	39.38±4.56	36.41±2.57	0.94±3.81	0.31±3.87
G7	51.88±4.59	42.60±1.12	51.01±3.30	38.73±2.33	15.70±4.16	1.62±5.00
G8	34.32±1.68	32.27±1.84	52.39±1.65	37.98±2.89	7.80±3.87	5.18±2.97
G9	36.02±1.48	31.78±0.45	45.06±2.25	24.20±4.88	14.55±3.25	10.36±3.54
G10	67.30±2.36	46.99±3.93	53.18±1.51	36.82±0.75	48.92±3.60	31.87±1.92
G11	59.94±2.42	46.19±4.16	36.52±1.80	35.14±2.55	19.94±4.73	5.86±4.26
G12	42.96±1.04	36.73±0.44	42.73±1.03	32.30±0.78	9.84±3.29	4.87±3.47
G13	40.62±1.03	36.23±2.66	29.09±2.40	27.65±3.04	25.54±4.29	24.96±1.47
G14	35.31±2.45	23.21±1.75	31.58±2.36	29.99±0.70	49.55±2.40	12.72±3.20
G15	35.78±2.25	32.77±3.36	45.59±3.21	28.75±1.99	28.57±4.05	24.39±2.36
G16	49.04±2.26	27.25±3.23	42.36±2.69	32.60±0.15	17.63±4.31	4.55±2.71
G17	69.14±4.77	38.36±1.38	45.70±3.80	19.90±0.52	22.45±1.41	19.31±3.60
G18	32.91±1.45	32.34±2.16	37.69±4.10	26.52±2.49	22.08±1.45	27.26±0.38
G19	47.56±1.65	30.36±3.61	35.51±1.39	26.11±4.35	38.88±1.91	36.42±3.56
G20	48.90±2.72	32.84±0.93	43.52±1.68	31.85±0.17	23.39±3.70	14.91±4.72
噻唑锌	75.30±1.62	58.21±2.34	52.30±1.15	35.90±2.65	68.23±1.28	50.36±3.17
中生菌素	52.32±2.38	43.31±1.68	51.20±3.02	33.52±2.19	65.35±3.12	46.53±2.82

Compd.	Activity/%	Compd.	Activity/%
G1	30±1.0	G12	57±2.5
G2	60±1.0	G13	57±1.5
G3	50±1.0	G14	40±1.0
G4	60±2.1	G15	30±1.0
G5	63±0.6	G16	30±1.0
G6	33±1.2	G17	53±1.5
G7	33±1.0	G18	40±1.0
G8	50±1.2	G19	67±0.6
G9	47±1.2	G20	47±1.2
G10	77±1.5	毒死蜱	100±0
G11	70±1.7	阿维菌素	100±0

Compd.	Activity/%	Compd.	Activity/%
G1	30±1.0	G12	57±2.5
G2	60±1.0	G13	57±1.5
G3	50±1.0	G14	40±1.0
G4	60±2.1	G15	30±1.0
G5	63±0.6	G16	30±1.0
G6	33±1.2	G17	53±1.5
G7	33±1.0	G18	40±1.0
G8	50±1.2	G19	67±0.6
G9	47±1.2	G20	47±1.2
G10	77±1.5	毒死蜱	100±0
G11	70±1.7	阿维菌素	100±0

含三氟甲基吡啶酰胺结构的N-氰基磺酰亚胺衍生物的合成及生物活性

Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide

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