新型吡唑双酰肼类化合物的合成及除草活性

Synthesis and herbicidal activity evaluation of novel diacylhydrazine derivatives containing pyrazolyl moiety

为了寻找具有较高除草活性的农药先导化合物,将吡唑环与双酰肼结构进行拼接,设计合成了13个未见报道的含吡唑环的双酰肼类目标化合物6a^6m,其结构均通过核磁共振氢谱及高分辨质谱确认。培养皿法测定结果表明:在200 mg/L下,化合物N'-(2-(2,4-二氯苯氧基)乙酰基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰肼(6i)对小麦Triticum aestivum、油菜Brassica campestris、高粱Sorghum bicolor、萝卜Raphanus sativus和黄瓜Cucumis sativus根、茎的抑制率均达80%以上。盆栽试验表明:在有效成分150 g/hm2剂量下,采用苗后茎叶喷雾处理,化合物6i对反枝苋Amaranthus retroflexus和鳢肠Eclipta prostrata的抑制率均达80%;相同剂量下采用苗前土壤喷雾处理,6i对反枝苋A.retroflexus的抑制率也达80%。

In order to discover pesticide lead compounds with high herbicidal activity, 13 novel diacylhydrazine derivatives containing pyrazolyl pharmacophore were designed and synthesized by introducing the pyrazolyl pharmacophore into the diacylhydrazine scaffold. Their structures were confirmed by 1H NMR and HRMS. The herbicidal activity of these compounds was evaluated. The dish test results indicated that the growth inhibition rates of the roots and stems of Triticum aestivum,Brassica campestris, Sorghum bicolor and Cucumi sativus were up to 80% for N’-（2-（2,4-dichlorophenoxy） acetyl）-3-（difluoromethyl）-1-methyl-1H-pyrazole-4-carbohydrazide（6i） at the dosage of200 mg/L. The pot test results showed that the growth inhibition rate of Amaranthus retroflexus and Eclipta prostrate for compound 6i were 80% by postemergence foliar spray processing at the dose of150 g/hm2; and compound 6i also demonstrated inhibition rate of 80% against A. retroflexus by preemergence soil spray processing at the same dose.