Yang Yan, Liu Yuxiu, Song Hongjian, Li Yongqiang, Wang Qingmin
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, China.
Mol Divers. 2016 Nov;20(4):919-932. doi: 10.1007/s11030-016-9687-6. Epub 2016 Jul 6.
Numerous compounds containing urea bridge and biurea moieties are used in a variety of fields, especially as drugs and pesticides. To search for novel, environmentally benign and ecologically safe pesticides with unique modes of action, four series of novel triazone analogues containing urea, thiourea, biurea, and thiobiurea bridge, respectively, were designed and synthesized, according to various calcium ion channel inhibitors which act on transient receptor potential protein. Their structures were characterized by [Formula: see text] NMR, [Formula: see text] NMR, and HRMS. The insecticidal activities of the new compounds were obtained. The bioassay results indicated that compounds containing a thiourea bridge and a thiobiurea bridge exhibited excellent insecticidal activities against bean aphid. Specifically, compounds [Formula: see text], [Formula: see text], and [Formula: see text] exhibited 85, 90, and 95 % activities, respectively, at 10 mg/kg. Compounds [Formula: see text] (30 %), [Formula: see text] (35 %), [Formula: see text] (30 %), and [Formula: see text] (40 %) exhibited the approximate aphicidal activity of pymetrozine (30 %) at 5 mg/kg. In addition, some target compounds exhibited insecticidal activities against lepidopteran pests. From a molecular design standpoint, the information obtained in this study could help in the further design of new derivatives with improved insecticidal activities.
许多含有脲桥和双脲部分的化合物被应用于各种领域，尤其是作为药物和杀虫剂。为了寻找具有独特作用方式的新型、环境友好且生态安全的杀虫剂，根据作用于瞬时受体电位蛋白的各种钙离子通道抑制剂，设计并合成了分别含有脲、硫脲、双脲和硫代双脲桥的四个系列新型三唑酮类似物。通过[化学式：见原文]核磁共振、[化学式：见原文]核磁共振和高分辨质谱对其结构进行了表征。获得了新化合物的杀虫活性。生物测定结果表明，含有硫脲桥和硫代双脲桥的化合物对豆蚜表现出优异的杀虫活性。具体而言，化合物[化学式：见原文]、[化学式：见原文]和[化学式：见原文]在10mg/kg时分别表现出85%、90%和95%的活性。化合物[化学式：见原文]（30%）、[化学式：见原文]（35%）、[化学式：见原文]（30%）和[化学式：见原文]（40%）在5mg/kg时表现出与吡蚜酮（30%）近似的杀蚜活性。此外，一些目标化合物对鳞翅目害虫表现出杀虫活性。从分子设计的角度来看，本研究获得的信息有助于进一步设计具有更高杀虫活性的新衍生物。
