含香豆素结构的芳氧苯氧丙酸酯衍生物的设计、合成及除草活性研究

Design,Synthesis and Herbicidal Activity of Aryloxyphenoxypropionate Derivatives Containing Coumarin Motif

为了开发新型芳氧苯氧丙酸酯类除草剂,采用活性亚结构拼接的方法,设计合成了一系列含香豆素结构的芳氧苯氧丙酸酯衍生物,其结构经1HNMR,13CNMR及高分辨质谱确证。利用平皿小杯法初步评价了目标化合物的除草活性,结果显示部分化合物对稗草表现出较好的抑制活性。其中,化合物CPP-4在100μg/mL浓度下对稗草的抑制率达到87.4%,与商品化除草剂-喹禾灵的抑制效果相当。温室盆栽实验结果显示,在土壤处理、1 500 g/hm2施药量情况下,化合物CPP-4对稗草和马唐呈现出很好的防除效果,抑制率达到80%以上。该研究结果表明,化合物CPP-4可以作为新型芳氧苯氧丙酸酯类除草剂的先导化合物继续优化。

To discover new aryloxyphenoxypropionate herbicides,a series of aryloxyphenoxypropionate derivatives containing coumarin motif was designed and synthesized using substructure splicing method.The structures of all target compounds were confirmed by 1 H NMR,13 C NMR and HRMS spectral data and their herbicidal activities were firstly evaluated.The preliminary bioassay results in vitro indicated that some of target compound displayed good herbicidal activity against monocotyledons,and especially compound CPP-4 had good herbicidal activities against Echinochloa crusgalli in vitro with 87.4%inhibition at a dose of 100μg/mL,which comparable to commercial herbicide quizalofop-ethyl.The greenhouse bioassay results showed that compound CPP-4 exhibited good herbicidal activities against Echinochloa crusgalli and Digitaria sanguinalis with inhibition>80%at a dosage of 1500 g/hm 2 under pre-emergence condition.The present work indicated that CPP-4 could be a potential lead structure for further development of novel aryloxyphenoxypropionate herbicides.