Citation: 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 shu

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

Zan Ningning ^a ,
Zhang Yulei ^b ,
Zhang Shuai ^a ,
Liu Si ^a ,
Jiang Lin ^a,,

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

Corresponding author: Jiang Lin, jiangl@sdau.edu.cn
Received Date: 5 May 2017
Revised Date: 1 June 2017
Available Online: 2 October 2017
Fund Project: Project supported by the Natural Science Foundation of Shandong Province (No.ZR2014BM030)the Natural Science Foundation of Shandong Province ZR2014BM030

Figures(2)

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.
- pyridine,
- ketones,
- oxime,
- carboxylic acids,
- synthesis design,
- antifungal activity
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