含喹唑啉-4-酮结构的芳氧苯氧丙酸二苯醚酯衍生物的设计、合成及除草活性研究

Design,Synthesis and Herbicidal Activity of Diphenyl Ether Aryloxyphenoxypropionate Derivatives Containing Quinazolin-4-one Motif

为了开发新型芳氧苯氧丙酸酯类除草剂,以前期工作发现的QPP-I为先导化合物,采用活性亚结构拼接法,设计、合成了19个含喹唑啉-4-酮结构的芳氧苯氧丙酸二苯醚酯衍生物,其结构经^(1)H NMR和^(13)C NMR确证。利用小杯平皿法初步测试除草活性发现,目标化合物对单子叶植物稗草具有较高的生长抑制率。其中,化合物QPPD-16在10ug/mL浓度下对稗草的生长抑制率达到81.6%,与商品化除草剂-精喹禾灵的抑制效果相当。利用温室盆栽法进一步测试除草活性发现,在土壤处理、750 g/hm2施药量情况下,化合物QPPD-16对稗草、马唐、狼尾草和狗尾草的生长抑制率分别为79.6%,83.1%,84.0%和70.0%。更重要的是,化合物QPPD-16对农作物大豆和花生具有较高的安全性。该研究结果表明,化合物QPPD-16具有作为芳氧苯氧丙酸酯类除草剂先导化合物的潜力。

To develop a new aryloxyphenoxypropionate herbicide,a total of 19 diphenyl ether aryloxyphenoxypropionate derivatives containing quinazolin-4-one motif were designed and synthesized using substructure splicing method based on the previous discovered QPP-I as the lead compound.Their structures were confirmed by ^(1)H NMR and ^(13)C NMR.The herbicidal activity of the target compound was tested by small cup plate method.It was found that the target compound had higher growth inhibition rate against the monocotyledon Echinochloa crus-galli with the growth inhibition rate 81.6%at the concentration of 10μg/mL,which was similar to the commercial herbicide quizalofop-p-ethyl.The results in a greenhouse test showed that the growth inhibition rates of compound QPPD-16 on Echinochloa crus-galli,Digitaria sanguinalis,Pennisetum alopecuroides and Setaria viridis were 79.6%,83.1%,84.0%and 70.0%,respectively,under pre-emergence conditions at a dosage of 750 g/hm 2.More importantly,the compound QPPD-16 has a high safety for crops such as soybean and peanut.The results showed that compound QPPD-16 has the potential to be developed as a novel aryloxyphenoxypropionate herbicide and can be further optimized as a lead compound.