Chinese Journal of Organic Chemistry >
Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity
Received date: 2017-05-05
Revised date: 2017-06-01
Online published: 2017-06-16
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
Zan Ningning , Zhang Yulei , Zhang Shuai , Liu Si , Jiang Lin . Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity[J]. Chinese Journal of Organic Chemistry, 2017 , 37(10) : 2767 -2771 . DOI: 10.6023/cjoc201705009
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