摘要/Abstract

为了开发含有巴比妥酸结构的新型β-三酮类除草剂，设计、合成了一系列5-酰基巴比妥酸衍生物，并测试了其除草活性.温室盆栽测试结果表明，在1500 g·ha^-1的剂量下，目标化合物1，3-二甲基-5-（2-（2-氯-4-氟苯氧基）-1-羟基亚乙基）嘧啶-2，4，6（1H，3H，5H）-三酮（BBA-22）和1，3-二甲基-5-（2-（2-溴-4-氟苯氧基）-1-羟基亚乙基）嘧啶-2，4，6（1H，3H，5H）-三酮（BBA-27）对所测杂草均具有优异的抑制活性.其中，化合物BBA-22在苗前处理187.5 g·ha^-1的剂量下，对油菜、苋菜和马唐具有很好的抑制活性，其活性优于商品除草剂2，4-二氯苯氧乙酸（2，4-D）.另外，以拟南芥为模型植物的分子作用机制研究表明，化合物BBA-22在植物体中被降解为相应的苯氧乙酸，这解释了其与生长素类除草剂具有相似除草机理的原因.本工作的研究结果表明，化合物BBA-22是其相应的苯氧乙酸生长素类除草剂的前药，可以用作进一步开发新型生长素型除草剂的先导化合物.
关键词: β-三酮, 5-酰基巴比妥酸, 合成, 除草剂, 苯氧乙酸
In an effort to develop novel β-triketone herbicides containing a barbituric acid moiety, a series of 5-acylbarbituric acid derivatives were designed, synthesized, and tested for herbicidal activity. The bioassay results showed that some of the target compounds, such as 5-(2-(2-chloro-4-fluorophenoxy)-1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (BBA-22) and 5-(2-(2-bromo-4-fluorophenoxy)-1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (BBA-27), exhibited excellent herbicidal activity against all tested weeds at a dosage of 1500 g·ha^-1. In particular, compound BBA-22 displayed good pre-emergent herbicidal activity against Brassica campestris, Amaranthus retroflexus and Digitaria sanguinalis even at a dosage of 187.5 g·ha^-1,surpassing that of a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D). Investigation of the molecular mode of action of compound BBA-22 upon treatment of Arabidopsis thaliana as a model plant revealed that BBA-22 was degraded to the corresponding phenoxyacetic acid, which explains why the herbicidal mechanism is similar to that of auxin-type herbicides. The present study demonstrates that compound BBA-22 is a proherbicide of the corresponding phenoxyacetic acid auxin herbicide and a potential lead compound for further development of novel auxin herbicides.
Key words: β-triketone, 5-acylbarbituric acid, synthesis, herbicide, phenoxyacetic


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