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

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 (LC50 = 2.9869 mg/kg), I-10 (LC50 = 3.4957 mg/kg), I-11 (LC50 = 2.3154 mg/kg), I-12 (LC50 = 4.1614 mg/kg), I-13 (LC50 = 2.1690 mg/kg), and I-14 (LC50 = 3.0077 mg/kg) exhibited much higher aphicidal activity than pymetrozine (LC50 = 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 (LC50 values were 0.6929 and 0.2592 mg/kg, respectively) against C. pipiens pallens.