Design, Synthesis, and Insecticidal Activities of New N-Benzoyl-N′-phenyl-N′-sulfenylureas

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• 作者：Ranfeng Sun ; Yonglin Zhang ; Li Chen ; Yongqiang Li ; Qingshan Li ; Haibin Song ; Runqiu Huang ; Fuchun Bi ; Qingmin Wang
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2009
• 出版时间：May 13, 2009
• 年：2009
• 卷：57
• 期：9
• 页码：3661-3668
• 全文大小：807K
• 年卷期：v.57,no.9(May 13, 2009)
• ISSN：1520-5118

文摘

A series of new N′-alkylaminothio, N′-arylaminothio (or dithio), and N′,N′-thio (or dithio) derivatives of N-benzoyl-N′-phenylureas were designed and synthesized as insect-growth regulators with sulfur dichloride or disulfur dichloride as the original reactant. The new compounds were identified by ¹H nuclear magnetic resonancee (NMR) spectroscopy, elemental analysis [or high-resolution mass spectrometry (HRMS)], and single-crystal X-ray diffraction analysis. The X-ray results demonstrated that there exist N−S−N or N−S−S−N bonds in these new compounds. In comparison to the parent N-benzoyl-N′-phenylureas, these derivatives displayed better solubility. The insecticidal activities of the target compounds were evaluated. The results of bioassays showed that compounds 1−24 retained the larvicidal activities of the corresponding benzoylphenylureas (BPUs) and some compounds exhibited better larvicidal activities against oriental armyworm and mosquitoes than the parent BPUs. The larvicidal activities of the selected target compounds 1 and 24 against diamondback moth were better than that of the corresponding parent compounds E and triflumuron.