α-萜品烯酰基农用杀菌活性物的合成及活性研究

doi:10.3969/j.issn.0253-2417.2022.06.006

林产化学与工业 ›› 2022, Vol. 42 ›› Issue (6): 39-46.doi: 10.3969/j.issn.0253-2417.2022.06.006

α-萜品烯酰基农用杀菌活性物的合成及活性研究

李璇¹(), 潘婷敏¹, 耿媛霄¹, 周海玉¹, 李健², 高艳清¹^,³^,*()

1. 西北农林科技大学植物保护学院；陕西省生物农药工程技术研究中心, 陕西杨凌 712100
2. 西北农林科技大学林学院, 陕西杨凌 712100
3. 广西民族大学；广西林产化学与工程重点实验室；广西林产化学与工程协同创新中心, 广西南宁 530006

收稿日期:2021-10-19 出版日期:2022-12-28 发布日期:2023-01-07
通讯作者: 高艳清 E-mail:lixuan1001@nwafu.edu.cn;gaoyanqinggc@nwsuaf.edu.cn
作者简介:高艳清, 副教授, 硕士生导师, 主要从事林业资源综合利用方面的研究；E-mail: gaoyanqinggc@nwsuaf.edu.cn
李璇(2001—), 女, 甘肃白银人, 本科生, 主要从事松节油新农药创制研究；E-mail: lixuan1001@nwafu.edu.cn
基金资助:
江苏省生物质能源与材料重点实验室开放基金(JSBEM202019);广西林产化学与工程重点实验室开放课题(GXFG 2009)

Synthesis and Antifungal/Anti-oomycete of Turpentine Based Derivatives

Xuan LI¹(), Tingmin PAN¹, Yuanxiao GENG¹, Haiyu ZHOU¹, Jian LI², Yanqing GAO¹^,³^,*()

1. Shaanxi Biopesticide Engineering & Technology Research Center; College of Plant Protection, Northwest A&F University, Yangling 712100, China
2. College of Forestry, Northwest A&F University, Yangling 712100, China
3. Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products; Guangxi Key Laboratory of Chemistry and Engineering of Forest Products; Guangxi University for Nationalities, Nanning 530006, China

Received:2021-10-19 Online:2022-12-28 Published:2023-01-07
Contact: Yanqing GAO E-mail:lixuan1001@nwafu.edu.cn;gaoyanqinggc@nwsuaf.edu.cn

摘要/Abstract

摘要：

以β-蒎烯为原料, 制备3个系列蒎烯基衍生物：二氢枯茗酸酰胺类化合物(5a~5g)、二氢枯茗酸肟酯类化合物(6a~6f)和二氢枯茗酸酰腙类化合物(8a~8f)，利用FT-IR、¹H NMR、MS对产物结构进行表征。采用菌丝生长速率法探讨了19种化合物的抑菌活性, 研究结果表明：19种化合物对苹果腐烂病菌、番茄灰霉病菌和辣椒疫霉均有抑制作用, 对苹果腐烂病菌的抑制作用较强, 其中化合物5a和8e对苹果腐烂病菌的半数有效质量浓度(EC₅₀)达到10.489和10.810 mg/L。通过初步构效关系研究发现：在化合物中引入卤素、氰基和硝基等电负性官能团能显著提高化合物的抑菌活性，其中化合物5a和8e可作为先导化合物进一步优化研究。

关键词: β-蒎烯, 含卤素衍生物, 抑菌活性

Abstract:

Three pinene-based derivatives of dihydrocuminic amides compounds(5a-5g), dihydrocuminic oxime esters compounds(6a-6f) and dihydrocuminic acyl hydrazones compounds(8a-8f) were prepared from β-pinene. The structurs of the product were characterized by FT-IR, ¹H NMR and MS. The bactericidal activities of the obtained compounds were investigated by mycelial growth rate method. The results showed that these 19 compounds had inhibitory effects on Valsa mali, Botrytis cinerea and Phytophthora capsici, where the inhibitory effect on V. mali was stronger. The half effective mass concentration(EC₅₀) values of compounds 5a and 8e against V. mali were 10.489 and 10.810 mg/L, respectively. The results of preliminary structure-activity relationship showed that the introduction of electronegative functional groups such as halogen atoms, cyano groups and nitro groups to the compounds could significantly improve the antibacterial activity of the compounds. Among them, 5a and 8e could be used as lead compounds for further optimization study.

Key words: β-pinene, halogen containing derivatives, antifungal activity

中图分类号:

TQ35
R914.5

李璇, 潘婷敏, 耿媛霄, 周海玉, 李健, 高艳清. α-萜品烯酰基农用杀菌活性物的合成及活性研究[J]. 林产化学与工业, 2022, 42(6): 39-46.

Xuan LI, Tingmin PAN, Yuanxiao GENG, Haiyu ZHOU, Jian LI, Yanqing GAO. Synthesis and Antifungal/Anti-oomycete of Turpentine Based Derivatives[J]. Chemistry and Industry of Forest Products, 2022, 42(6): 39-46.

图/表 5

图1

表1

图2

表2

图3

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化合物 compound	抑制率inhibitory rate/%
化合物 compound	苹果腐烂病菌 V. mali	番茄灰霉病菌 B. cinerea	辣椒疫霉 P. capsici
5a	90.6	27.9	—
5b	90.3	33.9	31.9
5c	45.6	32.0	20.0
5d	34.2	25.3	22.9
5e	30.2	22.6	56.6
5f	23.5	45.6	26.6
5g	22.4	42.8	22.3
6a	34.5	33.8	28.9
6b	50.7	34.5	27.9
6c	44.4	32.1	28.9
6d	45.6	22.1	44.4
6e	46.7	20.4	49.6
6f	47.6	25.9	12.1
8a	88.8	—	—
8b	85.9	24.1	12.9
8c	90.6	28.9	28.9
8d	87.6	27.9	32.3
8e	82.4	33.5	27.9
8f	88.9	34.7	26.3
多菌灵 carbendazim	100.0	25.9	17.4

化合物 compound	不同质量浓度下的抑制率inhibitory rate at different mass concn./%					EC₅₀/(mg·L^-1)	回归方程 regression equations	R²
化合物 compound	100 mg/L	50 mg/L	25 mg/L	12.5 mg/L	6.25 mg/L	EC₅₀/(mg·L^-1)	回归方程 regression equations	R²
5a	90.6	80.2	68.3	52.8	37.8	10.489	y=-0.318x+0.030	0.911
5b	90.3	79.5	62.7	50.4	30.0	17.016	y=-0.570x+0.033	0.903
5c	45.6	20.5	—	—	—	—	—	—
5d	34.2	—	—	—	—	—	—	—
5e	30.2	—	—	—	—	—	—	—
5f	23.5	—	—	—	—	—	—	—
5g	22.4	—	—	—	—	—	—	—
6a	34.5	—	—	—	—	—	—	—
6b	50.7	20.9	—	—	—	—	—	—
6c	44.4	33.5	—	—	—	—	—	—
6d	45.6	33.2	—	—	—	—	—	—
6e	46.7	20.5	—	—	—	—	—	—
6f	47.6	20.8	—	—	—	—	—	—
8a	82.4	69.2	56.4	45.8	35.5	21.360	y=-0.474x+0.022	0.941
8b	85.9	71.3	59.6	50.1	40.9	14.046	y=-0.319x+0.023	0.971
8c	90.6	73.2	61.1	51.2	43.0	12.198	y=-0.325x+0.027	0.992
8d	87.6	70.6	58.4	49.6	39.7	15.961	y=-0.391x+0.025	0.982
8e	90.2	75.6	62.3	52.3	42.7	10.810	y=-0.289x+0.027	0.981
8f	86.1	69.0	57.8	48.7	39.5	17.073	y=-0.395x+0.023	0.980

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α-萜品烯酰基农用杀菌活性物的合成及活性研究

Synthesis and Antifungal/Anti-oomycete of Turpentine Based Derivatives

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