Synthesis and Insecticidal/Fungicidal Activities of Triazone Derivatives Containing Acylhydrazone Moieties

A series of novel triazone derivatives containing aldehyde hydrazone or ketone hydrazone moieties were designed, synthesized and their biological activities were investigated against <i>Aphis craccivora</i>, <i>Culex pipiens pallens</i>, <i>Helicoverpa armigera</i>, <i>Ostrinia nubilalis</i>, <i>Mythimna separata</i> and 14 Kinds of fungi. Most of the aldehyde hydrazone exhibited excellent insecticidal activities against <i>A. craccivora</i>. In particular, the aphicidal activities of compounds <b>3t</b> (35%) and <b>3w</b> (30%) were equivalent to pymetrozine (30%) at 5 mg/kg. The aphicidal activities of derivatives <b>3p</b>, <b>3u</b>, <b>3y</b>, <b>5g</b>, <b>5i</b>, <b>5l</b>, <b>5q</b> and <b>5u</b> against <i>C. pipiens pallens</i> were higher than that of pymetrozine. Compound <b>3u</b> (100%) exhibited good larvicidal activities against <i>C. pipiens pallens</i> at 0.25 mg/kg. Most derivatives exhibited broad-spectrum fungicidal activities against 14 kinds of plant fungi at 50 mg/kg. Thirty-nine compounds exhibited a more than 50% inhibition rate against <i>Physalospora piricola</i>. Compounds <b>3h</b>, <b>3t</b> and <b>3w</b> were expected to be the leading structure for the development of new triazone insecticides agents.