Background: Benzoylureas are the most commonly used chitin synthesis inhibitors. But, the exact target site of benzoylurea insecticides has not been identified. Objective: To study whether benzoylphenylureas analogues with a bipartite model could be designed and synthesized as novel insecticides with improved activities. Methods: Based on the bipartite model of the sulfonylurea receptor binding site and commercial diflubenzuron, a series of novel benzoylureas containing carbamate groups were designed and synthesized via the key intermediate 2,6-difluoro-N-((4-hydroxyphenyl)carbamoyl)benzamide (2). The structures of the target compounds were confirmed by the 1H NMR and high-resolution mass spectrum (HRMS). Results: The results of bioassays indicated that these target compounds possessed good larvicidal activities against a broad spectrum of insects such as oriental armyworm (Mythimna Separata Walker), diamondback moth (Plutella xylostella), and mosquito (Culex pipiens pallens). A compound containing N, N-diisopropyl (3g) exhibited the highest insecticidal activity against oriental armyworm (40% at 10 mg kg-1), which was comparable with that of diflubenzuron. These compounds also had good larvicidal activities against diamondback moth and mosquito; most of these target compounds exhibited comparable larvicidal activities of diamondback moth with diflubenzuron and higher larvicidal activities of mosquito than diflubenzuron. Conclusion: The experimental data above preliminarily proved the rationality of our speculation and design ideology, and BPUs analogues with a bipartite model could improve the interaction with the target.

中文翻译：

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基于磺酰脲类受体结合位点二分模型的新型含氨基甲酸酯基苯甲酰脲类药物的设计、合成及杀虫评价

背景：苯甲酰脲类是最常用的几丁质合成抑制剂。但是，苯甲酰脲类杀虫剂的确切靶位点尚未确定。目的：研究是否可以设计合成具有二分体模型的苯甲酰苯基脲类类似物作为活性提高的新型杀虫剂。方法：基于磺酰脲类受体结合位点和商品化除虫脲的二分模型，通过关键中间体2,6-二氟-N-((4-羟苯基)氨甲酰基)苯甲酰胺设计合成了一系列含有氨基甲酸酯基团的新型苯甲酰脲类化合物。 (2). 目标化合物的结构经1H NMR和高分辨率质谱(HRMS)确证。结果：生物测定结果表明，这些目标化合物对东方粘虫 (Mythimna Separata Walker)、小菜蛾 (Plutella xylostella) 和蚊子 (Culex pipiens pallens) 等广谱昆虫具有良好的杀幼虫活性。含有 N,N-二异丙基 (3g) 的化合物对东方粘虫表现出最高的杀虫活性（10 mg kg-1 时为 40%），与除虫脲相当。这些化合物对小菜蛾和蚊子也有很好的杀幼虫活性；大多数这些目标化合物对小菜蛾的杀幼虫活性与除虫脲相当，对蚊子的杀幼虫活性高于除虫脲。结论：以上实验数据初步证明了我们推测和设计思想的合理性，