新型香豆素衍生物的设计、合成及除草活性研究

Design,Synthesis and Herbicidal Activity of Novel Coumarin Derivatives

以(未)取代的间苯二酚与β-酮酸酯类化合物为起始原料,在酸催化下发生Pechmann反应,合成了4个关键中间体:7-羟基香豆素衍生物(1a~1d),其与芳氧乙(丙)酰氯作用,合成了8个结构新颖的7-芳氧乙酰氧基香豆素衍生物(2a~2h),其结构经1 H NMR、13 C NMR和元素分析表征。油菜平皿法和稗草小杯法的测试结果表明,目标化合物对双子叶植物油菜根长的抑制效果好,与阳性对照药2,4-D相当,并表现出一定的构效关系。进一步的温室盆栽实验(50 g/亩)表明,茎叶处理时,部分目标化合物(如2a~2e)对双子叶植物的抑制率为100%,与2,4-D的防效相当,具有作为先导化合物进一步优化的价值。

Four intermediate compounds,7-hydroxycoumarin derivatives(1a~1d),were prepared based on improved Pechmann reaction using(un)substituted phenol andβ-ketoester as starting materials,then were treated with aryloxyacetyl/aryloxypropanoyl chloride to afford 8 new target compounds,7-aryloxyacetoxycoumarin derivatives(2a~2h).Their structures were characterized by 1 H NMR,13 C NMR and elemental analysis.The preliminary results of rape cup test and barnyardgrass cup test showed that the target compounds possessed excellent inhibition effect on the root growth of the dicotyledonous plant Brassica campestris.Further glasshouse tests demonstrated some of the target compounds(such as 2a~2e)showed high herbicidal activity against dicotyledonous plants at the dosage of 50 g/mu in post-emergence treatment,which were as potent as commercial herbicide 2,4-D.These results indicated that the target compounds had potentials as lead compounds for further optimization.