Design, Synthesis, and Insecticidal Activity of Novel Triazone Derivatives Containing Sulfonamide or Sulfonimide Moieties

作者：Yan Yang, Yuxiu Liu, Hongjian Song, Yongqiang Li, Qingmin Wang · 发表于：Journal of Agricultural and Food Chemistry · 年份：2021 · DOI：10.1021/acs.jafc.1c01925 · 被引用次数：25 · 研究领域：Insect-Plant Interactions and Control、Insect Pest Control Strategies、Insect and Pesticide Research

On the basis of sulfonamide moieties widely used in drugs and the mode of action of pymetrozine and the structures of some transient receptor potential channel antagonists and to improve the insecticidal activities of triazone insecticides, a series of triazone derivatives containing sulfonamide or sulfonimide moieties were designed, synthesized, and characterized. The bioassay results showed that most of these derivatives containing sulfonamide moieties exhibited excellent insecticidal activities against Aphis craccivora . Especially, (substituted)phenylsulfonylamino triazones I-9 (LC 50 = 2.9869 mg/kg), I-10 (LC 50 = 3.4957 mg/kg), I-11 (LC 50 = 2.3154 mg/kg), I-12 (LC 50 = 4.1614 mg/kg), I-13 (LC 50 = 2.1690 mg/kg), and I-14 (LC 50 = 3.0077 mg/kg) exhibited much higher aphicidal activity than pymetrozine (LC 50 = 6.0635 mg/kg). All monosulfonyl-substituted 4-amino-triazinones had better activities than the corresponding disulfonyl-substituted compounds. In addition, some derivatives also exhibited insecticidal activities against Culex pipiens pallens . Among Helicoverpa armigera, Mythimna separata, and Ostrinia nubilalis, compounds I-18 and I-21 exhibited good larvicidal activities (LC 50 values were 0.6929 and 0.2592 mg/kg, respectively) against C. pipiens pallens .