含氢化诺卜基的季铵盐类化合物对松枯梢病原菌的抑制作用及其机理研究

doi:10.3969/j.issn.0253-2417.2022.04.013

林产化学与工业 ›› 2022, Vol. 42 ›› Issue (4): 88-94.doi: 10.3969/j.issn.0253-2417.2022.04.013

含氢化诺卜基的季铵盐类化合物对松枯梢病原菌的抑制作用及其机理研究

昌家宇¹, 丁清颖¹, 肖转泉², 王宗德¹, 张骥¹, 陈尚钘¹^,*()

1. 江西农业大学林学院；国家林业草原木本香料(华东)工程技术研究中心，江西南昌 330045
2. 江西师范大学化学化工学院，江西南昌 330027

收稿日期:2022-02-25 出版日期:2022-08-28 发布日期:2022-09-01
通讯作者: 陈尚钘 E-mail:76866758@qq.com
作者简介:陈尚钘，教授，博士生导师，从事林产化工教学和科研工作；E-mail: 76866758@qq.com
昌家宇(1998—)，女，江西新余人，硕士生，主要从事植物资源化学利用研究工作
基金资助:
国家自然科学基金资助项目(31960295);江西省主要学科学术和技术带头人培养计划领军人才项目(20204BCJ22022);江西省重大科技研发专项资助项目(20203ABC28W016)

Inhibitory Effect and Mechanism of Quaternary Ammonium Salts Containing Hydrogenated Nobyl on Sphaeropsis sapinea

Jiayu CHANG¹, Qingying DING¹, Zhuanquan XIAO², Zongde WANG¹, Ji ZHANG¹, Shangxing CHEN¹^,*()

1. College of Forestry, Jiangxi Agricultural University; East China Woody Fragrance & Flavor Engineering Technology Research Center of National Forestry and Grassland Administration, Nanchang 330045, China
2. College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027, China

Received:2022-02-25 Online:2022-08-28 Published:2022-09-01
Contact: Shangxing CHEN E-mail:76866758@qq.com

摘要/Abstract

摘要：

测试了由β-蒎烯为起始原料合成得到的3个系列共36种含氢化诺卜基的季铵盐类化合物对松枯梢病原菌抑制率，并从松枯梢病菌菌丝干质量、细胞膜通透性及菌丝结构等3个方面，初步探究了双氢化诺卜基二甲基溴化铵(14)、六亚甲基-1, 6-双(氢化诺卜基二甲基氯化铵)(26)、四亚甲基-1, 4-双(氢化诺卜基二乙基溴化铵)(28)与1, 4-二苄基-双(氢化诺卜基二甲基溴化铵)(31)等4个化合物对松枯梢病原菌的抑菌机理。研究结果表明：大部分含氢化诺卜基的季铵盐类化合物对松枯梢病菌均有良好的抑制作用，且含有双氢化诺卜基的双子季铵盐对松枯梢病菌的抑制作用强于单季铵盐，多数含有双氢化诺卜基的季铵盐类化合物在质量浓度50 mg/L下的抑制率均达90%以上，甚至高达100%，抑制效果大大超过常用杀菌剂百菌清和多菌灵。初步的抑菌机理研究发现：4种化合物处理后松枯梢病菌的菌丝干质量减少，细胞膜通透性增加，相对电导率明显升高，菌丝体形态和结构发生明显变化。推测季铵盐类化合物可通过破坏病菌细胞膜的完整性和改变菌丝体形态与细胞结构来抑制松枯梢病菌的菌丝生长。

关键词: 氢化诺卜基, 季铵盐, 松枯梢病原菌, 抑菌作用, 抑菌机理

Abstract:

Three series of 36 quaternary ammonium salts containing hydrogenated nopyl were synthesized using β-pinene as the starting material. Their inhibitory rates on pathogenic fungi of Sphaeropsis sapinea were tested. The inhibitory mechanism of four compounds including bis(hydrogenated nopyldimethylammonium bromide)(14), hexamethylene-1, 6-bis(hydrogenated nopyldimethylammonium chloride)(26), tetramethylene-1, 4-bis(hydrogenated nopyldiethylammonium bromide)(28) and 1, 4-dibenzyl-bis(hydrogenated nopyldimethylammonium bromide)(31) on pathogenic fungi of S. sapinea were preliminarily explored from three aspects of mycelial dry weight, cell membrane permeability and mycelial structure. The results showed that most of the quaternary ammonium salt compounds containing hydrogenated nopyl had good inhibitory effect on S. sapinea, and the inhibitory effect of gemini quaternary ammonium salts containing hydrogenated nopyl on S. sapinea were stronger than that of single quaternary ammonium salts. The inhibitory rates of most quaternary ammonium salt compounds containing hydrogenated nopyl were more than 90% or even 100%, at a mass concentration of 50 mg/L, which were much higher than those of commonly used fungicides chlorothalonil and carbendazim. The preliminary antibacterial mechanism study showed that the dry weight of mycelium decreased, the relative conductivity increased significantly, and the morphology and structure of mycelium changed significantly when they were treated by above-mentioned four compounds. Based on these phenomena, we speculated that quaternary ammonium compounds could inhibit the mycelial growth of S. sapinea by damaging the integrity of cell membrane and changing the morphology and structure of mycelium.

Key words: hydrogenated nopyl, quaternary ammonium salt, Sphaeropsis sapinea, antifungal effect, antifungal mechanism

中图分类号:

TQ35
S432.2

昌家宇, 丁清颖, 肖转泉, 王宗德, 张骥, 陈尚钘. 含氢化诺卜基的季铵盐类化合物对松枯梢病原菌的抑制作用及其机理研究[J]. 林产化学与工业, 2022, 42(4): 88-94.

Jiayu CHANG, Qingying DING, Zhuanquan XIAO, Zongde WANG, Ji ZHANG, Shangxing CHEN. Inhibitory Effect and Mechanism of Quaternary Ammonium Salts Containing Hydrogenated Nobyl on Sphaeropsis sapinea[J]. Chemistry and Industry of Forest Products, 2022, 42(4): 88-94.

图/表 5

图1

表1

图2

图3

图4

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化合物 compound	抑制率/% inhibition rate (50 mg/L)	EC₅₀/(mg·L^-1)	毒力回归方程 toxic regression equation	化合物 compound	抑制率/% inhibition rate (50 mg/L)	EC₅₀/(mg·L^-1)	毒力回归方程 toxic regression equation
1	1.59	152.13	y=1.14x+2.51	20	100	4.81	y=4.78x+1.74
2	—	502.30	y=1.29x+1.51	21	100	4.58	y=4.66x+1.92
3	18.34	43.68	y=3.41x-0.59	22	100	4.02	y=4.30x+2.40
4	8.36	83.36	y=4.56x-3.76	23	100	5.35	y=4.76x+1.53
5	—	553.33	y=1.02x+2.20	24	100	13.53	y=2.20x+2.52
6	—	283.82	y=0.49x+3.80	25	100	3.92	y=4.50x+2.33
7	—	636.07	y=0.60x+3.32	26	100	3.29	y=4.22x+2.82
8	48.62	27.65	y=0.97x+3.60	27	100	12.49	y=5.01x+0.49
9	2.58	116.89	y=0.81x+3.32	28	100	11.93	y=4.91x+0.29
10	21.36	40.02	y=3.32x+0.32	29	98.11	16.95	y=5.11x-1.28
11	35.83	37.08	y=3.31x-0.19	30	100	12.76	y=3.21x+3.58
12	38.73	35.62	y=3.20x+0.04	31	100	4.18	y=4.77x-0.01
13	55.74	20.42	y=1.18x+3.45	32	100	5.91	y=5.61x+2.40
14	100	4.98	y=1.66x+3.85	33	100	11.90	y=3.63x+1.10
15	72.32	11.68	y=2.18x+2.68	34	93.83	7.93	y=4.67x+0.80
16	100	5.49	y=2.11x+3.44	35	100	6.53	y=5.11x+0.84
17	74.01	12.92	y=2.24x+2.51	36	73.75	10.35	y=5.18x-0.26
18	100	3.72	y=4.29x+2.55	百菌清 chlorothalonil	60.20	7.82	y=0.46x+4.59
19	100	4.62	y=4.64x+1.92	多菌灵 carbendazim	59.48	18.98	y=0.95x+3.79

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含氢化诺卜基的季铵盐类化合物对松枯梢病原菌的抑制作用及其机理研究

Inhibitory Effect and Mechanism of Quaternary Ammonium Salts Containing Hydrogenated Nobyl on Sphaeropsis sapinea

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