Synthesis and fungicidal activity of macrolactams and macrolactones with an oxime ether side chain

文献类型： 外文期刊

第一作者： Jia, Yue-Mei

作者： Jia, Yue-Mei;Liang, Xiao-Mei;Zhu, Wei-Juan;Zhang, Jian-Jun;Dong, Yan-Hong;Wu, Jin-Ping;Chen, Fu-Heng;Wang, Dao-Quan;Yuan, Hui-Zu;Qi, Shu-Hua

作者机构：

关键词： macrolactam;macrolactone;synthesis;fungicidal activity;fungicide;pesticide

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.279； 五年影响因子：5.269 ）

ISSN： 0021-8561

年卷期： 2007 年 55 卷 26 期

页码：

收录情况： SCI

摘要： Three series of novel macrolactams and macrolactones - 12-alkoxyimino-tetradecanlactam, 12-alkoxyiminopentadecanlactam, and 12-alkoxyiminodecanlactone derivatives (7A, 7B, and 7C) - were synthesized from corresponding 12-oxomacrolactams and 12-oxomacrolactone. Their structures were confirmed by H-1 NMR and elemental analysis. The Z and E isomers of 7A and 7B were separated, and their configurations were determined by H-1 NMR. These compounds showed fair to excellent fungicidal activities against Rhizoctonia solani Kuhn. It is interesting that the Z and E isomers of most of the compounds have quite different fungicidal activities. The fact that the compounds have a gradual increase of fungicidal activity in the order of 7A, 7C, and 7B indicated that the macrocyclic derivatives with a hydrogen-bonding acceptor (=N-O-) and a hydrogen-bonding donor (-CONH-) on the ring, and a three methylenes distance (CH2CH2CH2) between these two functional groups, exhibited the best fungicidal activity. The bioassay also showed that 7B not only has good fungicidal activity but also may have a broad spectrum of fungicidal activities.

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