Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (10): 2767-2771.DOI: 10.6023/cjoc201705009 Previous Articles     Next Articles



昝宁宁a, 张钰镭b, 张帅a, 刘思a, 姜林a   

  1. a 山东农业大学化学与材料科学学院 泰安 271018;
    b 山东农业大学水利土木工程学院 泰安 271018
  • 收稿日期:2017-05-05 修回日期:2017-06-01 发布日期:2017-06-16
  • 通讯作者: 姜林
  • 基金资助:


Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity

Zan Ningninga, Zhang Yuleib, Zhang Shuaia, Liu Sia, Jiang Lina   

  1. a College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018;
    b College of Water Conservancy and Civil Engineering, Shandong Agricultural University, Taian 271018
  • Received:2017-05-05 Revised:2017-06-01 Published:2017-06-16
  • Contact: 10.6023/cjoc201705009
  • Supported by:

    Project supported by the Natural Science Foundation of Shandong Province (No.ZR2014BM030).

A series of novel pyridine derivatives containing oxime esters have been synthesized from 3-methylpyridine, ethyl pivalate, hydroxylamine hydrochloride and substituted benzoic acid by addition, oximization and esterification reactions,which has the advantages of moderate reaction condition and high yield. Their structures were elucidated by IR, 1H NMR, 13C NMR and elemental analysis. Moreover, the target compounds were evaluated for their antifungal activity against two plant pathogens by the mycelium growth rate method. The results indicated that O-(4-bromobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3h) and O-(4-chlorobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3j) exhibited strong antifungal activity against S. sclerotiorum with EC50 values of 5.07 and 4.81 μg/mL, and 3h, 3j and O-(3,4-dichlorobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3l) displayed high antifungal activity against B. cinerea with EC50 values of 4.98, 5.44 and 6.34 μg/mL, respectively.

Key words: pyridine, ketones, oxime, carboxylic acids, synthesis design, antifungal activity