崔庆, 王娇, 谢龙观, 徐效华. 5-(2-呋喃基)-1,3-环己二酮衍生物的合成及除草活性[J]. 农药学学报, 2010, 12(4): 417-422.
    引用本文: 崔庆, 王娇, 谢龙观, 徐效华. 5-(2-呋喃基)-1,3-环己二酮衍生物的合成及除草活性[J]. 农药学学报, 2010, 12(4): 417-422.
    CUI Qing, WANG Jiao, XIE Long-guan, XU Xiao-hua. Synthesis and herbicidal activity of 5-(2-furanyl) cyclohexane-1,3-diones derivatives[J]. Chinese Journal of Pesticide Science, 2010, 12(4): 417-422.
    Citation: CUI Qing, WANG Jiao, XIE Long-guan, XU Xiao-hua. Synthesis and herbicidal activity of 5-(2-furanyl) cyclohexane-1,3-diones derivatives[J]. Chinese Journal of Pesticide Science, 2010, 12(4): 417-422.

    5-(2-呋喃基)-1,3-环己二酮衍生物的合成及除草活性

    Synthesis and herbicidal activity of 5-(2-furanyl) cyclohexane-1,3-diones derivatives

    • 摘要: 为了研究环己三酮类除草剂结构与活性的关系,以2-呋喃甲醛为起始原料,经过与丙酮的羟醛缩合(aldol condensation)反应、与丙二酸二乙酯的迈克尔加成反应、以及分子内的羟醛缩合环化反应,最后与酰氯发生重排反应合成了一系列新的5-(2-呋喃基)-1,3-环己二酮衍生物,所有目标化合物的结构均经过核磁共振氢谱、碳谱及高分辨质谱的确证。初步除草活性测定结果表明,与天然的AB5046A相比,2-苯甲酰基-5-(2-呋喃基)衍生物的活性明显降低,而2-乙酰基和丙酰基衍 生物则显示出更高的除草活性,如化合物 T3 在100 μ g/mL下对油菜生长的最高抑制率达82.9%。

       

      Abstract: In order to explore the structure-activity relationship of triketones,a series of 2-acyl-5-(2-furnayl)-cyclohexane-1,3-diones derivatives were synthesized starting from 2-furaldehyde via acetone aldol condensation and diethyl malonate Michel reaction,then intramolecular cyclization of aldol condensation.The structures of these compounds were confirmed by 1H NMR,13 C NMR and HRMS.The in vitro bioassay results showed that 2-benzoyl-5-(2-furanyl)-cyclohexane-1,3-diones show more low herbicidal activity than natural product AB5046A,and 2-acyl and propionyl derivatives have high herbicidal activity.Compound T3 showed 82.9% inhibition rate at the dosage of 100 μ g/mL against Brassica campestris L.

       

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