香豆素肟酯衍生物的合成及抑菌活性

袁含笑; 张文广; 刘函如; 张云天; 张彩霞; 郭孜怡; 高艳清; 雷鹏; 刘西莉

doi:10.16801/j.issn.1008-7303.2022.0078

香豆素肟酯衍生物的合成及抑菌活性

doi: 10.16801/j.issn.1008-7303.2022.0078

袁含笑^1,,
张文广¹,
刘函如¹,
张云天¹,
张彩霞^{1, 2},
郭孜怡¹,
高艳清^{1, 2},
雷鹏^{1, 2, ,},
刘西莉^1, ,

1.
西北农林科技大学植物保护学院，陕西杨凌 712100
2.
陕西省生物农药工程技术研究中心，陕西杨凌 712100

基金项目: 陕西省技术创新引导专项 (2020QFY07-03)；陕西省专项经费 (F2020221004)；省级大学生创新创业训练计划项目 (S202210712432).

详细信息

作者简介:
袁含笑，153327297_yuan@nwafu.edu.cn

通讯作者:
雷鹏，peng.lei@nwafu.edu.cn

刘西莉，seedling@nwafu.edu.cn

中图分类号: TQ 450.11
计量
- 文章访问数: 371
- HTML全文浏览量: 100
- PDF下载量: 87
- 被引次数: 0
出版历程
- 收稿日期: 2022-07-06
- 录用日期: 2022-08-11
- 网络出版日期: 2022-08-18
- 刊出日期: 2022-10-10

Synthesis and antifungal activity of coumarin oxime esters

YUAN Hanxiao^1
,,
ZHANG Wenguang¹,
LIU Hanru¹,
ZHANG Yuntian¹,
ZHANG Caixia^{1, 2},
GUO Ziyi¹,
GAO Yanqing^{1, 2},
LEI Peng^{1, 2
, ,},
LIU Xili^{1
, ,}

1.
College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China
2.
Shaanxi Research Center of Biopesticide Engineering & Technology, Yangling 712100, Shaanxi Province, China

Funds: the Technology Innovation Guidance Special Fund of Shaanxi Province (2020QFY07-03); Special Fund of Shaanxi Province (F2020221004); Shaanxi Province Undergraduate Training Program for Innovation and Entrepreneurship (S202210712432)

摘要

摘要: 为发现具有高抑菌活性的肟酯类化合物, 结合本课题组前期研究, 设计并合成了18个新型香豆素肟酯衍生物, 并对抑菌活性及构效关系进行了研究。离体生物活性测定结果表明, 目标化合物在50 μg/mL下对番茄灰霉病菌、苹果树腐烂病菌和水稻纹枯病菌均表现出一定的抑制活性, 其中化合物 4n 对番茄灰霉病菌和水稻纹枯病菌的EC₅₀值分别为4.44 μg/mL和3.65 μg/mL，表现出比香豆素和肟菌酯更优或相似的活性。
- 香豆素 /
- 磺酸酯 /
- 肟酯 /
- 抑菌活性 /
- 水稻纹枯病菌
Abstract: In order to discover high antifungal activity oxime esters compound, based on our previous studies, 18 novel coumarin oxime esters were designed and synthesized. The antifungal activity was evaluated and the structure-activity relationship was analyzed. The in vitro bioassay results showed that the target compounds showed antifungal activities against Botrytis cinerea, Valsa mali and Rhizoctonia solani. Especially, compound 4n displayed excellent activity against B. cinerea (EC₅₀ = 4.44 μg/mL) and R. solani (EC₅₀ = 3.65 μg/mL), which are better than or similar to those of coumarin and trifloxystrobin.
- coumarin /
- sulphonate /
- oxime ester /
- antifungal activity /
- Rhizoctonia solani

HTML全文

1 香豆素、蛇床子素、丁香菌酯和ZXL的化学结构式

1. Structural formulas of coumarin, osthol, coumoxystrobin and ZXL

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2 本研究组前期及本文中肟酯类化合物的结构式

2. Structural formulas of oxime esters in our previous work and this paper

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3 目标化合物的合成路线

3. Synthetic route of target compounds

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4 化合物4a的化学结构式

4. Structural formula of compound 4a

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表 1 目标化合物4a~4r在50 μg/mL下离体抑菌活性

Table 1. Antifungal activities in vitro of target compounds 4a-4r at 50 μg/mL

化合物 Compd.	取代基 R	抑制率 Inhibition rate/%
化合物 Compd.	取代基 R	苹果树腐烂病菌 V. mali	番茄灰霉病菌 B. cinerea	水稻纹枯病菌 R. solani
4a	2-OMePh	37.4	25.4	35.6
4b	3-OMePh	0.4	2.7	23.5
4c	4-OMePh	24.5	8.1	29.1
4d	2-ClPh	8.9	19.2	26.1
4e	3-ClPh	4.7	1.5	1.6
4f	4-ClPh	3.5	16.5	2.6
4g	2-MePh	21.0	13.5	32.0
4h	4-MePh	16.3	16.9	16.3
4i	2-CF₃Ph	55.6	50.0	36.9
4j	3-CF₃Ph	9.3	13.5	3.6
4k	2-FPh	21.4	13.8	30.7
4l	2-BrPh	20.6	13.8	22.9
4m	3-BrPh	0.4	10.4	1.6
4n	Furan-2-yl	43.2	86.5	96.3
4o	t-Bu	22.2	29.6	96.9
4p	n-Bu-4-Cl	40.9	34.1	66.2
4q	n-Pr	43.5	63.9	82.6
4r	Thiophen-2-yl	43.3	57.9	65.5
香豆素 coumarin	—	39.1	45.2	76.3
肟菌酯 trifloxystrobin	—	97.4	77.7	89.3

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表 2 部分目标化合物对两种病原菌的EC₅₀值

Table 2. EC₅₀ values of some target compounds against two pathogenic fungi

病原菌 Pathogenic fungi	化合物 Compound	取代基 R	回归方程 Regression equation	决定系数 R²	EC₅₀/(μg/mL)	95% 置信限 95% CL/(μg/mL)
番茄灰霉病菌 B. cinerea	4n	Furan-2-yl	y = 0.889x − 0.576	0.957	4.44	3.10~5.90
番茄灰霉病菌 B. cinerea	肟菌酯 trifloxystrobin	—	y = 0.975x − 0.955	0.978	9.54	7.42~12.33
水稻纹枯病菌 R. solani	4n	Furan-2-yl	y = 1.270x − 0.714	0.935	3.65	1.83~5.65
	4o	t-Bu	y = 1.221x − 0.657	0.923	3.45	2.59~4.34
	4q	n-Pr	y = 1.202x − 1.230	0.962	10.55	8.59~13.08
	香豆素 coumarin	—	y = 1.056x − 1.202	0.981	13.75	10.89~17.91
	肟菌酯 trifloxystrobin	—	y = 0.959x − 0.634	0.939	4.58	3.31~5.56

下载: 导出CSV

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