Synthesis, Fungicidal Activity, and Structure-Activity Relationship of Spiro-Compounds Containing Macrolactam (Macrolactone) and Thiadiazoline Rings

文献类型： 外文期刊

第一作者： Li, Jian-Jun

作者： Li, Jian-Jun;Liang, Xiao-Mei;Jin, Shu-Hui;Zhang, Jian-Jun;Chen, Fu-Heng;Wang, Dao-Quan;Yuan, Hui-Zhu;Qi, Shu-Hua

作者机构：

关键词： Spiro-compounds;macrolactam;macrolactone;thiadiazoline;fungicidal activity

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：

年卷期：

页码：

收录情况： SCI

摘要： Two series of novel spiro-compounds containing macrolactam or macrolactone and thiadiazoline rings, 1-thia-2-alkylimino-3,4,9-triaza-10-oxospiro[4.15]eicosyl-3-ene (4F) and 1 -thia-2-alkylimino-3,4-diaza-9-oxa-10-oxospiro[4.15]eicosyl-3-ene (4G), were synthesized from 12-oxo-1,15-pentade-canlactam and 12-oxo-1,15-pentadecanlactone, respectively. Their structures were confirmed by elemental analysis, ~1H NMR, and ~(13)C NMR The conformation of compounds 4F was determined via the crystal structure of a representative compound (4F6). The bioassay showed that compounds 4F have much better fungicidal activity against five fungi (Bolrytis cinerea Pers., Sclerotlnia sclerotiorum, Rhlzoctonia solani Kiihn., Phomopsls asparagi Sacc., and Pyricularia oryzae Cav.) than compounds 4G. The fact above showed that the presence of a hydrogen-bonding donor for the fungicidal activity of macrocyclic compounds is very important. 4F6 showed excellent fungicidal activity against P. oryzae, which is much better than the commercial fungicide isoprothiolane, and 4F_(13) showed excellent fungicidal activity against P. oryzae and good fungicidal activity against P. asparagi.

分类号： R15

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