含三氟甲基吡啶结构的酰胺类衍生物的合成、表征及生物活性研究

doi:10.6023/cjoc202101045

有机化学 ›› 2021, Vol. 41 ›› Issue (8): 3303-3311.DOI: 10.6023/cjoc202101045 上一篇下一篇

研究简报

含三氟甲基吡啶结构的酰胺类衍生物的合成、表征及生物活性研究

何凤, 郭声鑫, 代阿丽, 张仁凤, 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:2021-01-26 修回日期:2021-03-15 发布日期:2021-05-25
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(111 Program, No. D20023); 贵州省科技技术基金([2017]1402); 及贵州省科技技术基金([2017]5788)

Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties

Feng He, Shengxin Guo, Ali Dai, Renfeng Zhang, 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:2021-01-26 Revised:2021-03-15 Published:2021-05-25
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, No. D20023); Science & Technology Planning Project of Guizhou Province([2017]1402); Science & Technology Planning Project of Guizhou Province([2017]5788)

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摘要/Abstract

合成了一系列含三氟甲基吡啶结构的酰胺衍生物, 并测试了它们对水稻白叶枯病菌(Xanthomonas oryzae pv. oryzae)、柑橘溃疡病菌(Xanthomonas axonopodis pv. citri)、烟草青枯病菌(Ralstonia solanacearum)的体外抑菌活性和对小菜蛾(Plutella xylostella)的杀虫活性. 结果表明, 部分化合物表现出优异的抑菌活性. 如2-((3-氯-5-(三氟甲基)吡啶-2-基)氧基)-N-(4-氟-2-甲基苯基)乙酰胺(6d)对水稻白叶枯病菌的EC₅₀值为54.1 mg•L^–1, 低于叶枯唑(EC₅₀=59.6 mg•L^–1)和噻菌酮(EC₅₀=86.3 mg•L^–1). 2-((3-氯-5-(三氟甲基)吡啶-2-基)氧基)-N-(4-氟-3(三氟甲基)苯基)乙酰胺(6h)和2-((3-氯- 5-(三氟甲基)吡啶-2-基)氧基)-N-(5,6-二氯吡啶-3-基)乙酰胺(6z)对柑橘溃疡病菌的抑制活性(EC₅₀值为51.2和60.7 mg• L^–1)均高于商品药剂叶枯唑(EC₅₀=76.3 mg•L^–1)和噻菌酮(EC₅₀=101.7 mg•L^–1). N-(2-氯-4-氟苯基)-2-((3-氯-5-(三氟甲基)吡啶-2-基)氧基)乙酰胺(6e)对烟草青枯病菌的抑菌活性略高于噻菌酮(EC₅₀=79.0 mg•L^–1), EC₅₀值为74.9 mg•L^–1. 此外, 化合物6e和2-((3-氯-5-(三氟甲基)吡啶-2-基)氧基)-N-(3-异丙基苯基)乙酰胺(6k)在浓度为500 mg•L^–1时表现出中等程度的杀小菜蛾活性.

关键词: 三氟甲基吡啶, 酰胺衍生物, 合成, 抗细菌活性, 杀虫活性

A series of novel trifluoromethylpyridine amide derivatives were synthesized and evaluated in vitro for their antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and Ralstonia solanacearum, and insecticidal activity against Plutella xylostella. Some of the compounds showed promising antibacterial activity. In particular, the half maximal effective concentration (EC₅₀) of 2-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)-N-(4-fluoro- 2-methylphenyl)acetamide (6d) was 54.1 mg•L^–1 against Xoo, which was slightly lower than the bismerthiazol (59.6 mg•L^–1) and thiodiazole copper (86.3 mg•L^–1) positive controls. 2-((3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)-N-(4-fluoro-3- (trifluoromethyl)phenyl)acetamide (6h) and 2-((3-chloro-5-(trifluoro-methyl)pyridin-2-yl)oxy)-N-(5,6-dichloropyridin-3-yl)- acetamide (6z) exhibited much higher activity against Xac (EC₅₀ 51.2 and 60.7 mg•L^–1, respectively) than bismerthiazol (76.3 mg•L^–1) and thiodiazole copper (101.7 mg•L^–1). N-(2-Chloro-4-fluorophenyl)-2-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)- oxy)acetamide (6e) showed good bioactivity against R. solanacearum with an EC₅₀ (74.9 mg•L^–1) lower than thiodiazole copper (79.0 mg•L^–1). 6e and 2-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)-N-(3-isopropylphenyl)acetamide (6k) at 500 mg• L^–1 exhibited moderate insecticidal activity against P. xylostella.

Key words: trifluoromethylpyridine, amide derivatives, synthesis, antibacterial activity, insecticidal activity

引用此文

何凤, 郭声鑫, 代阿丽, 张仁凤, 吴剑. 含三氟甲基吡啶结构的酰胺类衍生物的合成、表征及生物活性研究[J]. 有机化学, 2021, 41(8): 3303-3311.

Feng He, Shengxin Guo, Ali Dai, Renfeng Zhang, Jian Wu. Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3303-3311.

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Compd.	Xoo		Xac		R. solanacearum
Compd.	100 mg•L^–1	50 mg•L^–1	100 mg•L^–1	50 mg•L^–1	100 mg•L^–1	50 mg•L^–1
6a	26.7±0.4	20.6±4.5	47.5±0.6	38.5±1.8	44.1±0.9	28.4±3.0
6b	31.6±2.6	24.8±1.1	48.3±1.7	40.9±1.2	26.2±4.0	22.5±1.1
6c	33.0±1.1	22.2±4.1	38.2±1.6	27.0±1.7	31.4±4.4	22.0±4.2
6d	61.7±3.4	47.3±1.0	41.3±2.1	37.4±2.6	18.0±2.5	14.6±3.1
6e	32.8±3.1	27.4±1.9	44.2±3.8	36.0±2.8	58.5±2.4	41.2±1.6
6f	39.1±3.0	27.6±4.3	48.3±2.6	35.3±3.8	43.3±2.9	28.0±3.6
6g	32.1±2.7	21.0±4.8	40.9±3.2	35.7±3.9	7.8±0.1	5.6±2.3
6h	41.3±3.8	36.5±1.3	59.2±4.3	45.7±4.5	42.4±2.4	9.1±3.2
6i	26.4±1.3	11.3±3.5	48.7±1.2	41.9±3.7	29.4±2.5	19.0±4.1
6j	30.0±4.5	20.9±1.9	44.6±3.2	38.5±2.9	31.0±3.3	30.3±0.1
6k	37.5±1.2	26.4±2.1	40.0±3.0	25.6±3.8	31.7±3.9	28.3±1.7
6l	30.5±3.7	15.0±0.9	47.4±1.0	34.4±4.1	41.4±2.2	21.2±1.6
6m	37.0±3.9	31.4±3.1	40.0±0.7	29.4±4.0	41.0±3.2	25.5±2.2
6n	33.2±4.1	20.9±4.2	48.2±4.2	40.6±3.2	44.3±4.8	38.0±1.0
6o	25.7±2.0	6.7±0.1	40.5±3.2	36.4±3.0	12.1±3.7	8.1±3.3
6p	5.8±3.9	3.9±0.4	48.2±2.9	36.5±1.7	38.2±0.8	24.7±3.6
6q	29.4±4.0	20.0±4.7	42.1±3.0	23.3±2.6	28.1±3.5	25.3±3.5
6r	31.6±0.7	17.7±3.3	45.1±2.3	30.0±3.3	20.4±4.7	12.7±1.1
6s	35.7±1.9	20.9±4.5	40.1±3.1	30.1±4.2	45.9±2.1	30.4±4.5
6t	36.5±3.2	20.3±2.0	45.0±2.1	35.3±2.7	33.0±1.9	20.0±3.3
6u	31.8±3.1	25.1±2.4	45.7±2.6	41.7±2.2	48.2±1.7	33.8±3.3
6v	41.6±2.8	29.5±3.5	44.4±2.5	25.7±0.4	31.1±3.9	16.8±3.0
6w	15.8±1.2	10.0±2.0	34.1±2.5	20.1±3.5	44.6±4.5	24.7±2.8
6x	44.5±0.5	35.3±1.6	41.8±3.1	32.9±1.8	40.8±1.8	28.2±4.2
6y	38.3±5.0	23.9±2.7	47.7±3.1	32.8±3.0	44.5±1.4	36.0±1.7
6z	26.6±2.8	15.5±2.4	61.8±3.6	53.4±3.0	32.8±3.6	25.9±3.2
6aa	39.4±1.6	25.3±4.8	43.9±3.1	35.6±2.8	41.9±2.9	18.1±3.0
6ab	34.2±2.9	17.5±4.9	44.8±2.0	33.8±2.5	18.4±1.8	19.0±0.5
BT	58.8±2.0	41.2±3.7	56.1±1.9	46.6±0.4	52.5±2.2	46.7±2.3
TC	55.9±2.4	41.0±1.4	51.2±1.1	40.1±0.5	50.7±0.4	42.8±1.9

Compd.	Xoo		Xac		R. solanacearum
Compd.	100 mg•L^–1	50 mg•L^–1	100 mg•L^–1	50 mg•L^–1	100 mg•L^–1	50 mg•L^–1
6a	26.7±0.4	20.6±4.5	47.5±0.6	38.5±1.8	44.1±0.9	28.4±3.0
6b	31.6±2.6	24.8±1.1	48.3±1.7	40.9±1.2	26.2±4.0	22.5±1.1
6c	33.0±1.1	22.2±4.1	38.2±1.6	27.0±1.7	31.4±4.4	22.0±4.2
6d	61.7±3.4	47.3±1.0	41.3±2.1	37.4±2.6	18.0±2.5	14.6±3.1
6e	32.8±3.1	27.4±1.9	44.2±3.8	36.0±2.8	58.5±2.4	41.2±1.6
6f	39.1±3.0	27.6±4.3	48.3±2.6	35.3±3.8	43.3±2.9	28.0±3.6
6g	32.1±2.7	21.0±4.8	40.9±3.2	35.7±3.9	7.8±0.1	5.6±2.3
6h	41.3±3.8	36.5±1.3	59.2±4.3	45.7±4.5	42.4±2.4	9.1±3.2
6i	26.4±1.3	11.3±3.5	48.7±1.2	41.9±3.7	29.4±2.5	19.0±4.1
6j	30.0±4.5	20.9±1.9	44.6±3.2	38.5±2.9	31.0±3.3	30.3±0.1
6k	37.5±1.2	26.4±2.1	40.0±3.0	25.6±3.8	31.7±3.9	28.3±1.7
6l	30.5±3.7	15.0±0.9	47.4±1.0	34.4±4.1	41.4±2.2	21.2±1.6
6m	37.0±3.9	31.4±3.1	40.0±0.7	29.4±4.0	41.0±3.2	25.5±2.2
6n	33.2±4.1	20.9±4.2	48.2±4.2	40.6±3.2	44.3±4.8	38.0±1.0
6o	25.7±2.0	6.7±0.1	40.5±3.2	36.4±3.0	12.1±3.7	8.1±3.3
6p	5.8±3.9	3.9±0.4	48.2±2.9	36.5±1.7	38.2±0.8	24.7±3.6
6q	29.4±4.0	20.0±4.7	42.1±3.0	23.3±2.6	28.1±3.5	25.3±3.5
6r	31.6±0.7	17.7±3.3	45.1±2.3	30.0±3.3	20.4±4.7	12.7±1.1
6s	35.7±1.9	20.9±4.5	40.1±3.1	30.1±4.2	45.9±2.1	30.4±4.5
6t	36.5±3.2	20.3±2.0	45.0±2.1	35.3±2.7	33.0±1.9	20.0±3.3
6u	31.8±3.1	25.1±2.4	45.7±2.6	41.7±2.2	48.2±1.7	33.8±3.3
6v	41.6±2.8	29.5±3.5	44.4±2.5	25.7±0.4	31.1±3.9	16.8±3.0
6w	15.8±1.2	10.0±2.0	34.1±2.5	20.1±3.5	44.6±4.5	24.7±2.8
6x	44.5±0.5	35.3±1.6	41.8±3.1	32.9±1.8	40.8±1.8	28.2±4.2
6y	38.3±5.0	23.9±2.7	47.7±3.1	32.8±3.0	44.5±1.4	36.0±1.7
6z	26.6±2.8	15.5±2.4	61.8±3.6	53.4±3.0	32.8±3.6	25.9±3.2
6aa	39.4±1.6	25.3±4.8	43.9±3.1	35.6±2.8	41.9±2.9	18.1±3.0
6ab	34.2±2.9	17.5±4.9	44.8±2.0	33.8±2.5	18.4±1.8	19.0±0.5
BT	58.8±2.0	41.2±3.7	56.1±1.9	46.6±0.4	52.5±2.2	46.7±2.3
TC	55.9±2.4	41.0±1.4	51.2±1.1	40.1±0.5	50.7±0.4	42.8±1.9

Compd.	Xoo		Xac		R. solanacearum
Compd.	Regression equation	EC₅₀/(mg•L^–1)	Regression equation	EC₅₀/(mg•L^–1)	Regression equation	EC₅₀/(mg•L^–1)
6d	y=1.39x+2.60	54.1±4.41
6e					y=1.15x+2.81	74.9±2.75
6h			y=1.19x+3.30	51.2±6.02
6z			y=2.68x+0.25	60.7±2.84
BT	y=0.88x+3.4	59.6±2.42	y=1.59x+2.00	76.3±2.17
TC	y=0.95x+3.2	86.3±7.69	y=1.34x+2.30	101.7±1.71	y=1.21x+2.70	79.0±3.78

Compd.	Xoo		Xac		R. solanacearum
Compd.	Regression equation	EC₅₀/(mg•L^–1)	Regression equation	EC₅₀/(mg•L^–1)	Regression equation	EC₅₀/(mg•L^–1)
6d	y=1.39x+2.60	54.1±4.41
6e					y=1.15x+2.81	74.9±2.75
6h			y=1.19x+3.30	51.2±6.02
6z			y=2.68x+0.25	60.7±2.84
BT	y=0.88x+3.4	59.6±2.42	y=1.59x+2.00	76.3±2.17
TC	y=0.95x+3.2	86.3±7.69	y=1.34x+2.30	101.7±1.71	y=1.21x+2.70	79.0±3.78

Compd.	Mortality rate/%	Compd.	Mortality rate/%
6a	40±5	6p	20±5
6b	50±0	6q	30±0
6c	40±0	6r	40±0
6d	40±5	6s	40±0
6e	60±0	6t	30±5
6f	30±0	6u	20±0
6g	50±0	6v	20±0
6h	30±3.3	6w	20±0
6i	20±0	6x	30±3.3
6j	20±0	6y	40±0
6k	60±0	6z	20±0
6l	30±0	6aa	30±0
6m	40±2.9	6ab	30±0
6n	40±0	Chlorpyrifos	100±0
6o	20±0	Avermectin	100±0

含三氟甲基吡啶结构的酰胺类衍生物的合成、表征及生物活性研究

Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties

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