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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (06): 753-757. 上一篇    下一篇

研究论文

3-取代苄基-6-三氟甲基嘧啶-2,4(1H,3H)-二酮衍生物的合成及其除草活性的研究

朱有全，邹小毛*，李公春，姚昌盛，司学凯，杨华铮*   

  1. (南开大学元素有机化学国家重点实验室及元素有机化学研究所 天津 300071)
  • 收稿日期:2006-07-14 修回日期:2006-08-29 发布日期:2007-05-21
  • 通讯作者: 邹小毛

Synthesis and Herbicidal Evaluation of 3-Substituted Benzyl-6- (trifluoromethyl)pyrimidine-2,4(1H,3H)-dione Deriva-tives

ZHU You-Quan, ZOU Xiao-Mao*, LI Gong-Chun, YAO Chang-Sheng
SI Xue-Kai, YANG Hua-Zheng*   

  1. (State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemis-try,
    Nankai University, Tianjin 300071)
  • Received:2006-07-14 Revised:2006-08-29 Published:2007-05-21
  • Contact: YANG Hua-Zheng

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为了进一步研究3-取代苄基-6-三氟甲基嘧啶-2,4(1H,3H)-二酮衍生物的除草活性, 以期发现更高活性化合物, 合成了16个未见文献报道的3-取代苄基-6-三氟甲基嘧啶-2,4(1H,3H)-二酮衍生物, 其结构均经过1H NMR, IR和元素分析确证. 生测结果表明, 嘧啶环1-位取代基的变化, 不仅影响化合物的抑制活性与选择性, 可能还改变了化合物的作用方式. 定量的结构与活性关系研究表明, 当作用对象为油菜时, 化合物的活性可能主要与取代基R的摩尔分子折射常数有关; 当作用对象为稗草时, 化合物的活性可能主要与取代基R的电性参数有关. 1-位为氢时, 有利于对油菜生长的抑制; 1-位为甲基时, 有利于对稗草生长的抑制.

关键词: 6-三氟甲基嘧啶-2,4(1H,3H)-二酮, 定量构效关系, 除草剂

In order to further study the herbicidal activity of 3-substituted benzyl-6-(trifluoro- methyl)pyrimidine-2,4(1H,3H)-dione derivatives and find new herbicides, sixteen new 3-substituted benzyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione derivatives were syn-thesized and confirmed by 1H NMR, IR spectra and elemental analysis. The bioassay results showed that the title compounds herbicidal activity, selectivity and action mode were influenced by the sub-stituent at 1-position for pyrimidine ring. Quantitative structure-activity relationship studies showed that when the test grass was rape, their herbicidal activity was mainly related with substituent molar refractivity (MR); when the test grass was barnyard grass, their herbicidal activity was mainly related with the electronic parameters of the substituents at the para-position of benzene ring. When the substituent at 1-position for pyrimidine ring was hydrogen, the inhibition against rape was improved, while when the substituent at 1-position for pyrimidine ring was methyl group, the inhibition against barnyard grass was improved.

Key words: 6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, quantitative structure-activity relationship, herbicide