Synthesis and insecticidal evaluation of novel N-oxalyl derivatives of tebufenozide.

A series of novel N '-tert-butyl-N '-3,5-dimethylbenzoyl-N-aryloxyoxalyl-N-4-ethylbenzoyl hydrazines containing a carboxylic acid or ester substituent on the aryl were synthesized, and their larvicidal activities were evaluated. The results of bioassays indicated that some of these title compounds exhibit higher larvicidal activities than RH5849 (N-tert-butyl-N,N '-dibenzoylhydrazine), but they are not good compared to the parent compound (tebufenozide). The carboxylic acid substituent on the aryl was essential for high larvicidal activity. Compared to the parent compound, these derivatives displayed different physical properties, for example, better solubility in organic solvents. Toxicity assays indicated that these derivatives could induce a premature, abnormal, and lethal larval molt.