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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (11): 1768-1773. 上一篇    下一篇

研究简报

含2,4-咪唑啉二酮的环十二酮衍生物的合成及杀菌活性

陈守聪，张春艳，刘吉平，王道全，王明安*   

  1. (中国农业大学应用化学系 北京 100193)
  • 收稿日期:2010-03-08 修回日期:2010-05-12 发布日期:2010-07-08
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn, wangmingan2003@yahoo.com

Synthesis and Fungicidal Activity of Cyclododecanone Derivatives with Hydantoin

CHEN Shou-Cong, ZHANG Chun-Yan, LIU Ji-Ping, WANG Dao-Quan, WANG Ming-An   

  1. (Department of Applied Chemistry, China Agricultural University, Beijing 100193)
  • Received:2010-03-08 Revised:2010-05-12 Published:2010-07-08

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1362

被引次数

21 | 5

以环十二酮为原料合成α-取代环十二酮和α-取代环十二二酮, 再与2,4-咪唑啉二酮膦酸酯和2-硫代-2,4-咪唑啉二酮分别发生Wittig-Horner反应和Knoevenagel缩合反应, 合成了一系列目标化合物, 它们的化学结构通过IR, 1H NMR, 13C NMR和元素分析进行了表征. 初步生物活性测试结果表明, 部分化合物10, 11A, 11B, 12A, 12B, 13A, 14B和16在50 mg/mL浓度时对芦笋茎枯、茄绵疫以及油菜菌核病菌均有优良的抑制活性, 抑制率在70%～98%之间, 进一步的生物测试结果表明, 化合物12B, 13A和14B对芦笋茎枯的EC50值分别为15.80, 31.34和44.26 mg/mL.

关键词: α-取代环十二二酮, Wittig-Horner反应, Knoevenagel缩合反应, 杀菌活性

A series of novel cyclododecanone derivatives containing hydantoin/thiohydantoin were synthesized by the Wittig-Horner reaction and Knoevenagel condensation of α-substituted cyclododecanone and α-substituted 1,2-cyclododecandione prepared from cyclododecanone with hydantoin phosphate or thiohydantoin. Their structures were confirmed by IR, 1H NMR, 13C NMR spectra and elemental analysis. The preliminary bioassay showed that some of compounds such as 10, 11A, 11B, 12A, 12B, 13A, 14B and 16 exhibited good to excellent fungicidal activities with the range of 70%～98% inhibitory ratio against Phomopsis asparagi, Phytophthora parasitica and Sclerotinia sclerotiorum at the concentration of 50 mg/mL, the precise determination of EC50 data for 12B, 13A and 14B were 15.80, 31.34 and 44.26 mg/mL against P. asparagi, respectively.

Key words: α-substituted 1,2-cyclododecandione, Wittig-Horner reaction, knoevenagel condensation, fungicidal activity