氢化诺卜基二甲基烷基卤化铵的合成及抑菌活性
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摘要
由氢化诺卜基二甲基胺与9种卤代烃反应制得含氢化诺卜基的季铵盐化合物(氢化诺卜基二甲基烷基卤化铵),分别为氢化诺卜基二甲基乙基溴化铵(2a)、氢化诺卜基二甲基正丙基溴化铵(2b)、氢化诺卜基二甲基正丁基溴化铵(2c)、氢化诺卜基二甲基正戊基溴化铵(2d)、氢化诺卜基二甲基苄基溴化铵(2e)、氢化诺卜基二甲基苄基氯化铵(2f)、氢化诺卜基二甲基乙基碘化铵(2g)、氢化诺卜基二甲基正丙基碘化铵(2h)、氢化诺卜基二甲基正丁基碘化铵(2i)。采用红外光谱和核磁共振表征了它们的结构,并用菌丝生长速率法测试了9种化合物对8种植物病原真菌的抑制效果,结果表明:在药液质量浓度为500 mg/L下,9种化合物对8种供试病原菌均具有一定的抑制效果,其中2d的抑菌效果最好,对层出镰刀菌、梨链格孢菌、辣椒菌核病菌、毛竹枯梢病菌、松枯梢病菌的抑菌率均达到100%,2b、2c和2f也具有优异的抑菌性能,对辣椒菌核病菌的抑菌率均达到100%。
Nine hydronopol quaternary ammonium salts(hydronopol dimethyl alkyl ammonium halide), which were hydronopol dimethyl ethyl ammonium bromide(2 a),hydronopol dimethyl n-propyl ammonium bromide(2 b), hydronopol dimethyl n-butyl ammonium bromide(2 c), hydronopol dimethyl n-pentyl ammonium bromide(2 d), hydronopol dimethyl benzyl ammonium bromide(2 e), hydronopol dimethyl benzyl ammonium chloride(2 f), hydronopol dimethyl ethyl ammonium iodide(2 g), hydronopol dimethyl n-propyl ammonium iodide(2 h), and hydronopol dimethyl n-butyl ammonium iodide(2 i),were synthesized by the reaction of hydronopol dimethyl amine and 9 halogenated hydrocarbons, respectively. The identification and structural analysis were carried out by using FT-IR, MS and NMR methods, and the inhibition effects of the nine compounds on eight plant pathogens were tested by the method of mycelium growth rate method. The results showed that under the concentration of 500 mg/L, 9 compounds had certain inhibitory effects on the 8 plant pathogenic fungi, among which the bacteriostatic performance of 2 d were the best, the bacteriostatic rates against Fusarium proliferatum, Alternaria kikuchiana, Sclerotinia sclerotiorum, Ceratosphaeria phyllostachydis, and Sphaeropsis sapinea reached 100%, and 2 b, 2 c and 2 f also had excellent results, the bacteriostatic rate reached 100%.
Nine hydronopol quaternary ammonium salts(hydronopol dimethyl alkyl ammonium halide), which were hydronopol dimethyl ethyl ammonium bromide(2 a),hydronopol dimethyl n-propyl ammonium bromide(2 b), hydronopol dimethyl n-butyl ammonium bromide(2 c), hydronopol dimethyl n-pentyl ammonium bromide(2 d), hydronopol dimethyl benzyl ammonium bromide(2 e), hydronopol dimethyl benzyl ammonium chloride(2 f), hydronopol dimethyl ethyl ammonium iodide(2 g), hydronopol dimethyl n-propyl ammonium iodide(2 h), and hydronopol dimethyl n-butyl ammonium iodide(2 i),were synthesized by the reaction of hydronopol dimethyl amine and 9 halogenated hydrocarbons, respectively. The identification and structural analysis were carried out by using FT-IR, MS and NMR methods, and the inhibition effects of the nine compounds on eight plant pathogens were tested by the method of mycelium growth rate method. The results showed that under the concentration of 500 mg/L, 9 compounds had certain inhibitory effects on the 8 plant pathogenic fungi, among which the bacteriostatic performance of 2 d were the best, the bacteriostatic rates against Fusarium proliferatum, Alternaria kikuchiana, Sclerotinia sclerotiorum, Ceratosphaeria phyllostachydis, and Sphaeropsis sapinea reached 100%, and 2 b, 2 c and 2 f also had excellent results, the bacteriostatic rate reached 100%.
引文
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[3]张强华,纪丽莲. 芦竹内生真菌F0238对植物病原菌的拮抗作用[J]. 微生物学通报,2004,31(2):82-85. ZHANG Q H,JI L L. Antagonistic effect of endophytic fungus F0238 of Arundo donax L. on plant pathogenic bacteria[J]. Microbiology Bulletin,2004,31(2):82-85.
[4]聂臻,姚占力,牛字得,等. 油田注水用杀菌剂在我国的应用及发展[J]. 石油与天然气化工,1999,28(4):304-308. NIE Z,YAO Z L,ZHU Z D,et al. Application and development of biocide water injection fungicide in China[J]. Petroleum and Natural Gas Chemical Industry,1999,28(4):304-308.
[5]赵晓雷,张跃军. 季铵盐杀生剂杀生性能与机理研究进展[J]. 精细化工,2010,27(12):1144-1150. ZHAO X L,ZHANG Y J. Research progress on biocidal properties and mechanism of quaternary ammonium salt biocides[J]. Fine Chemical Industry,2010,27(12):1144-1150.
[6]王应红. 壳聚糖及其季铵盐与离子液体复配用于皮革防霉性能研究[J]. 西部皮革,2003,34(2):200-206. WANG Y H. Study on the antifungal properties of chitosan and its quaternary ammonium salt mixed with ionic liquids for leather[J]. Western leather,2003,34(2):200-206.
[7]李明春,许涛,辛梅华. 壳聚糖及其衍生物的抗菌活性研究进展[J]. 化工进展,2011,31(1):203-209. LI M C,XU T,XIN M H. Research progress on antibacterial activity of chitosan and its derivatives[J]. Chemical Industry,2011, 31(1):203-209.
[8]雷万学,林霞,林芳,等. 季铵盐型魔芋葡甘聚糖衍生物的合成表征及生物学活性[J]. 光谱学与光谱分析,2008,28(5):1030-1034. LEI W X,LIN X,LIN F,et al. Synthesis and biological activity of quaternary ammonium-type konjac glucomannan derivatives[J]. Spectroscopy and Spectral Analysis,2008,28(5):1030-1034.
[9]赵玲华,肖转泉,陈金珠,等. 氢化诺卜醇及其卤代物的合成与结构分析[J]. 林产化学与工业,2012,32(1):39-42. ZHAO L H ,XIAO Z Q,CHEN J Z,et al. Synthesis and structural analysis of hydronol and its halides[J]. Chemicals and Industry of Forest Products,2012,32(1):39-42.
[10]赵玲华,肖转泉,陈金珠,等. 氢化诺卜醇及其烷基醚的合成与表征[J]. 化学研究与应用,2012,24(1):123-126. ZHAO L H ,XIAO Z Q,CHEN J Z,et al. Synthesis and identification of hydronol and its alkyl ethers[J]. Chemical Research and Application,2012,24(1):123-126.
[11]陈金珠,肖转泉,徐丽峰,等. 含氢化诺卜基的叔铵类化合物的合成与结构分析[J]. 江西师范大学学报:自然科学版,2016,40(2):179-182. CHEN J Z,XIAO Z Q,XU L F,et al. The synthesis and structural analysis of hydronopyl tertiary amine copounds[J]. Journal of Jiangxi Normal University:Natural Science,2016,40(2):179-182.
[12]吴文君. 植物化学保护实验技术导论[M]. 西安:陕西科学技术出版社,1988:333. WU W J. Introduction to Experimental Techniques of Phytochemical Protection[M]. Xi'an:Shaanxi Science and Technology Press,1988:333.
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[14]ZHANG H M,ZHOU W Y,ZHANG W Y,et al. Inhibitory effects of citral,cinnamaldehyde,and tea polyphenols on mixed biofilm formation by foodbome Staphylococcus aureus and Salmonella enteritidis[J]. Journal of Food Protection,2004,77(6):33-92.