含吡啶杂环氯化铵阳离子表面活性剂的杀菌活性

doi:10.3969/j.issn.1001-1803.2020.05.006

摘要/Abstract

摘要：

旨在筛选具有较好的水溶性、绿色环保、对植物病原菌具有较强杀菌性的杀菌剂。利用琼脂平板稀释法测定不同碳链长度的含吡啶杂环氯化铵（简称C8,C10,C12,C14,C16）阳离子表面活性剂对四种植物病原菌的离体杀菌活性,求出毒力回归方程,并计算有效抑菌浓度EC₅₀值。结果表明：碳链长度为12的含吡啶杂环氯化铵（C12）阳离子表面活性剂对水稻纹枯病原菌的EC₅₀=9.69×10 ^-3 g/L、对照药井岗霉素的EC₅₀=7.02×10 ^-2 g/L;对西瓜枯萎病原菌的EC₅₀=2.93×10 ^-2 g/L、对照药甲基布拖津的EC₅₀=0.506 g/L;对苹果腐烂病原菌的EC₅₀=1.57×10 ^-5 g/L、对照药苯醚甲环唑的EC₅₀=3.50×10 ^-4 g/L;对番茄灰霉病原菌的EC₅₀=1.85×10 ^-4 g/L、对照药菌恶唑的EC₅₀=2.04×10 ^-3 g/L。即C12对四种病原菌的EC₅₀值明显低于对照药剂,具有较好的杀菌活性,具有进一步研究的价值。通过相同试验方法进一步得到C12对四种病原菌的最小抑菌浓度（MIC）分别为0.094,0.091,0.083和0.087 g/L。为含吡啶杂环氯化铵阳离子表面活性剂对植物病原菌的防治研究提供依据。

关键词: 含吡啶杂环氯化铵阳离子表面活性剂, 植物病原菌, 离体, 最小抑菌浓度, 杀菌活性

Abstract:

The purpose is to screen fungicides with good water solubility, environmental protection and strong bactericidal effect on plant pathogens. The bactericidal activity of pyridine-containing heterocyclic ammonium chloride cationic surfactants with different carbon chain lengths （C8, C10, C12, C14, C16） against four kinds of plant pathogens was tested by agar plate dilution method. The toxicity regression equation was obtained, and the effective antibacterial concentration （EC₅₀） was calculated. The results show that the pyridine-containing heterocyclic ammonium chloride cationic surfactants with a carbon chain length of 12 （C12） has a significant antibacterial activity for Rhizoctonia solani Kühn, watermelon Fusarium wilt, apple valsa canker and Botrytis cinerea Pers. with the EC₅₀ of 9.69×10 ^-3, 2.93×10 ^-2, 1.57×10 ^-5 and 1.85×10 ^-4g/L, respectively. While the EC₅₀of the control drugs containing jinggangmycin, methyl butazine, difenoconazole and mycoazole for the above plant pathogens individually are 7.02×10 ^-2, 0.506, 3.50×10 ^-4 and 2.04×10 ^-3 g/L, respectively. The EC₅₀ value of C12 for four pathogens are significantly lower than the control drugs, which has good bactericidal activity and further research value. The minimal inhibitory concentration （MIC） of C12 against the four plant pathogens are 0.094, 0.091, 0.083 and 0.087 g/L, respectively. It provides the basis for the research on the prevention and treatment of plant pathogens by pyridine-containing heterocyclic ammonium chloride cationic surfactants.

Key words: pyridine-containing heterocyclic ammonium chloride cationic surfactants, plant pathogens, in vitro, minimum inhibitory concentration, fungicidal activity

中图分类号:

TQ423.12

李云晴,王丽艳,唐丽,刘家庆,杜昱瀛,吴定成. 含吡啶杂环氯化铵阳离子表面活性剂的杀菌活性[J]. 日用化学工业, 2020, 50(5): 314-318.

LI Yun-qing,WANG Li-yan,TANG Li,LIU Jia-qing,DU Yu-ying,WU Ding-cheng. Bactericidal activity of pyridine-containing heterocyclic ammonium chloride cationic surfactants[J]. China Surfactant Detergent & Cosmetics, 2020, 50(5): 314-318.

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参考文献 25

[1]	Ahemed I, Mnal M . Structure and biological behaviors of some metallo cationic surfactants[J]. Journal of Surfactants and Detergents, 2013,16(5) : 709-715.
[2]	Li Yintao . Study on the bactericidal ability of pyrldine-quatemary ammonium salt surfactants[J]. Journal of Changzhi Medical College, 2010,24(1) : 10-12.
[3]	Zhou Fei, Sun Yuhan, Zhang Lizhi , et al. Synjournal and antibacterial characteristics of eco-friendly quaternary ammonium salt bactericide[J]. Environmental Science & Technology, 2011,34(5) : 39-42.
[4]	Mao Xueqiang, He Shuai, Li Jun , et al. Synjournal and antibacterial properties of quaternary ammonium Gemini surfactants[J]. Chinese Journal of Synthetic Chemistry, 2011,19(2) : 180-183.
[5]	Pei L J, Cai Z S, Shang S B , et al. Synjournal and properties of a cationic Gemini surfactant with the hydrophenanthrene structure[J]. Journal of Surfactants and Detergents, 2014,17(3) : 433-439.
[6]	Wang L Y, Qin H L, Wang L , et al. Synjournal and properties of 1- (2- (alkyl amino) -2-oxo ethyl) pyridinium chloride surfactants[J]. Journal of Chemical Research, 2013,4:205-207.
[7]	Aia I, Emam D, Eideeb A , et al. Novel imidazolium-based Gemini surfactants: synjournal, surface properties, corrosion inhibition and biocidal activity against sulfate-reducing bacteria[J]. Journal of Surfactants and Detergents, 2013,16(5) : 927-935.
[8]	Wang Liyan, He Xianyou, Liu Shifu , et al. Properties of cationic surfactants containing thiazole heterocyclic structure[J]. Speciality Petrochemicals, 2018,35(2) : 44-47.
[9]	Cao Yu, Shi Boan, Chen Yan . Synjournal and activity of double thiadiazole-based α-aminophosphonates[J]. Fine Chemicals, 2012,29(1) : 49-52.
[10]	Xu Wangjin, Chen Kaiyi, Liu Jianbing . Synjournal and biological activity of diamide compounds containing 5-aminothiazole ring[J]. Fine Chemicals, 2018,35(4) : 645-651.
[11]	He Haifeng, Xia Qin, He Hongwu . Synjournal and biological evaluation of pyrimidine derivatives containing hydrazine structural unit[J]. Chinese Journal of Organic Chemistry, 2019,39:2295-2302.
[12]	Yang Hongliang, Jin Bo, Chen Jianqing . Synjournal and biological activity of pyridinyl-4,5-2H-isoxazole heterocyclic derivatives[J]. Fine Chemicals, 2019,36(3) : 487-493.
[13]	Li Sunyong, Bo Rui, Li Yuanxiang . Synjournal and biological activity of 2-substituted-4-chloro-5-aryl-2H-1,2,3-triazole derivatives[J]. Fine Chemicals, 2019,36(5) : 951-956.
[14]	Zhang Ling, Ma Wenxiu, Ren Zuohua , et al. 7 Fungicides: indoor toxicity determination on Magnaporthe oryzae and Rhizoctonia solani[J]. Chinese Agricultural Science Bulletin, 2018,34(20) : 126-129.
[15]	Deng Kunxue, Huang Qigu . Advances in agrochemical surfactants[J]. Chemical Industry and Engineering Progress, 2009,28(12) : 2199-2204.
[16]	Wang L Y, Sun L, Wang L , et al. Synjournal and characterisation of new N-alkyl-N, N-dimethyl[N- (pyridin-2-yl) carbamoyl]methylammonium chlorides[J]. Journal of Chemical Research, 2013,12:733-735.
[17]	Anant K, Ghumare B V, Pawar S . Synjournal and antibacterial activity of novel amido-amine-based cationic Gemini surfactants[J]. Journal of Surfactants and Detergents, 2013,16(5) : 85-93.
[18]	Li Jiele, Zhou Xiaomao . Toxicity of 5 fungicides to Rhizoctonia solani Kühn in lab[J]. Modern Agricultural Science and Technology, 2011,8:181-183.
[19]	Guo Yuehua, Zheng Zhuohui, Zhang Deyong , et al. Toxicity of 10 fungicides to corn leaf blight Kühn in lab[J]. Guangdong Agricultural Sciences, 2012,4:65-66.
[20]	Yang Mei, Yang Yingqing, Li Minghai , et al. Effects of jinggangmycin on the growth and development of Rhizoctonia solani Kühn causal agent of rice sheath blight[J]. Journal of Huazhong Agricultural University, 2012,31(4) : 445-449.
[21]	Zhao Jie, Tang Zhaolian, Zhou Chaoying , et al. Toxicity test of five fungicides to Fusarium osysporum f. sp. Niveum and Fusarium osysporum f. sp. Cucumerinum[J]. Chinese Horticulture Abstracts, 2012,8:39-40.
[22]	Xu Yan, Luo feng, Yang Lizhe , et al. Toxicity of several fungicides to watermelon Fusarium wilt[J]. Tropical Agricultural Science & Technology, 2010,30(10) : 18-20.
[23]	Suolang Lamu . The sensitivity of Valsa spp. to difenoconazole and azoxystrobin[D]. Xian: Northwest A& F University, 2010.
[24]	Ma Jianying, Zhang Xiaofeng, Wang Wenqiao , et al. The sensitivity of botrytis cinerea to SYP-Z048 and cross resistance against diverse fungicides[J]. Journal of Plant Protection, 2009,36(1) : 61-64.
[25]	Zhao Jianxi, Mao Ning, You Yi . Bactericidal activities of some quaternary Gemini surfactants in relation with their molecules structures[J]. Chinese Journal of Applied Chemistry, 2003,20(12) : 1208-1210.

表面活性剂	菌丝生长抑制率/%
表面活性剂	0.005 g/L	0.020 g/L	0.080 g/L
C8	31.14	35.28	51.81
C10	36.51	46.83	81.03
C12	46.33	58.05	92.37
C14	36.30	47.54	87.30
C16	34.94	40.18	77.03

化合物	毒力回归方程	EC₅₀/（g·L^-1）
C8	y=2.756 1 x +0.297 7	7.34×10^-2
C10	y=6.876 5 x +0.330 8	2.46×10^-2
C12	y=7.814 9 x +0.424 2	9.69×10^-3
C14	y=7.478 1 x +0.325 9	2.25×10^-2
C16	y=3.493 3 x +0.331 9	4.81×10^-2
井冈霉素	—	7.02×10^-2

表面活性剂	毒力回归方程
表面活性剂	西瓜枯萎病原菌	苹果腐烂病原菌	番茄灰霉病原菌
C8	y = 1.815 0 x +0.100 9	y =4.305 6 x +0.274 4	y =5.468 0 x +0.287 6
C10	y = 6.615 7 x +0.056 42	y =6.132 0 x +0.462 5	y =4.289 7 x +0.435 6
C12	y =10.450 5 x +0.193 8	y =6.336 4 x +0.499 9	y =6.500 4 x +0.498 8
C14	y = 4.108 4 x +0.085 77	y =4.888 3 x +0.465 1	y =4.798 2 x +0.437 9
C16	y = 3.311 2 x +0.115 9	y =4.146 7 x +0.341 2	y =4.922 0 x +0.397 8

化合物	EC₅₀/（g·L^-1）
化合物	西瓜枯萎病原菌	苹果腐烂病原菌	番茄灰霉病原菌
C8	0.219	5.24×10^-2	3.88×10^-2
C10	6.70×10^-2	6.11×10^-3	1.50×10^-2
C12	2.93×10^-2	1.57×10^-5	1.85×10^-4
C14	8.57×10^-2	7.13×10^-3	1.29×10^-2
C16	0.116	3.83×10^-2	2.08×10^-2
甲基托布津	0.506	—	—
苯醚甲环唑	—	3.50×10^-4	—
菌恶唑	—	—	2.04×10^-3