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Chemistry and Industry of Forest Products ›› 2018, Vol. 38 ›› Issue (3): 103-108.doi: 10.3969/j.issn.0253-2417.2018.03.014

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Synthesis and Antifungal Activity of Ethylene Glycol Mono Hydronopol Ether and Its Carboxylic Ester

HUANG Jing1, XIAO Zhuanquan2, WANG Zongde1, FAN Guorong1   

  1. 1. College of Forestry, Jiangxi Agriculture University, Camphor Tree Engineering and Technology Research Center of State Forestry Administration and Jiangxi Province, Nanchang 330045, China;
    2. College of Chemistry, Jiangxi Normal University, Nanchang 330027, China
  • Received:2017-12-09 Online:2018-06-25 Published:2018-06-22

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

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