乙二醇单氢化诺卜基醚及其羧酸酯的合成与抑菌活性

doi:10.3969/j.issn.0253-2417.2018.03.014

摘要/Abstract

摘要： 由氢化诺卜基溴（1）与乙二醇在氢氧化钠作用下合成乙二醇单氢化诺卜基醚（2），再与5种羧酸进行酯化反应制得乙二醇单氢化诺卜基醚的5种羧酸酯，分别为乙二醇单氢化诺卜基醚甲酸酯（3a）、乙二醇单氢化诺卜基醚乙酸酯（3b）、乙二醇单氢化诺卜基醚丙酸酯（3c）、乙二醇单氢化诺卜基醚正丁酸酯（3d）和乙二醇单氢化诺卜基醚正戊酸酯（3e），5种产品得率和GC纯度均在90%以上。利用红外光谱（FT-IR）、核磁共振（¹H NMR，¹³C NMR）分析表征2和3a~3e的结构，并采用菌丝生长速率法测试了6个化合物对10种植物病原真菌的抑制作用，结果表明：在药液质量浓度500 mg/L时，6个化合物对10种植物病原真菌都有一定的抑制作用，其中化合物2对拟茎点霉菌、油茶炭疽病菌、辣椒菌核病菌、水稻纹枯病菌、毛竹枯梢病菌的抑制率均高达100%，化合物3a对辣椒菌核病菌、猕猴桃果实拟茎点霉菌及莴苣菌核病菌的抑制率均高达100%，高于或等同于相同质量浓度下百菌清对这些病原真菌的抑制率。

关键词: 氢化诺卜基溴, 乙二醇单氢化诺卜基醚, 酯化反应, 结构分析, 抑菌活性

Abstract: Ethylene glycol mono hydronopol ether(compound 2)was prepared from the reaction of hydronopol bromide and ethylene glycol under the alkaline condition provided by sodium hydroxide. And then, five kinds of ethylene glycol mono hydronopol ether carboxylic esters, which were ethylene glycol mono hydronopyl ether ester (3a), ethylene glycol mono hydronopyl ether acetate (3b), ethylene glycol single hydronopyl ether propionate (3c), ethylene glycol mono hydronopyl ether ester of butyric acid (3d), ethylene glycol mono hydronopyl ether n-valeric acid ester (3e), were prepared from the esterification of ethylene glycol mono hydronopol with five carboxylic acids, respectively, and the yields and GC purities of products were all above 90%. Identification and structural analysis were performed by NMR(¹H NMR, ¹³C NMR) and FT-IR. The antifungal activities of all compounds against ten plant pathogenic fungi were studied by measuring the mycelial growth rate. The antifugal activity test showed that at the mass concentration of 500 mg/L, the six compounds had certain antifungal activity against the ten tested plant pathogenic fungi. Among these inhibitory rate data, the inhibition rate of compound 2 on Phomopsis chimonanthi, Glomerella cingulata, Sclerotinia sclerotiorum, Thanatephorus cucumeris, Ceratosphaeria phyllostachydis reached 100%, the inhibition rate of compound 3a on S. sclerotiorum, Botryis phariadothide and Lettuce sclerotinia reached 100%, the inhibition rates of these compounds even exceeded or were equal to chlorothalonil on the same mass concentration.

Key words: hydronopol bromide, ethylene glycol mono hydronopol ether, esterification, structural analysis, antifungal activity

中图分类号:

TQ35

黄晶, 肖转泉, 王宗德, 范国荣. 乙二醇单氢化诺卜基醚及其羧酸酯的合成与抑菌活性[J]. 林产化学与工业, 2018, 38(3): 103-108.

HUANG Jing, XIAO Zhuanquan, WANG Zongde, FAN Guorong. Synthesis and Antifungal Activity of Ethylene Glycol Mono Hydronopol Ether and Its Carboxylic Ester[J]. Chemistry and Industry of Forest Products, 2018, 38(3): 103-108.

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