Synthesis and insecticidal activity of benzoheterocyclic analogues of N ′‐benzoyl‐ N ‐( tert ‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues

The N ′‐benzoyl group of N ‐ tert ‐butyl‐ N ′‐benzoyl‐3,5‐dimethylbenzohydrazide ( 1 ) was converted to a series of benzoheterocyclecarbonyl groups in order to investigate the potential usefulness of superimposing a hydrazine insecticide on 20‐hydroxyecdysone. A series of analogues with benzodioxole, benzodioxane, benzodioxapine, indole, benzoxazole, benzoxazine or benzothiazole instead of the phenyl group of ( 1 ) were synthesized and tested for their insecticidal activity against the common cutworm ( Spodoptera litura F). N ‐ tert ‐Butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐1,3‐benzodioxole‐5‐carbohydrazide and N ‐ tert ‐butyl‐ N ′‐(3,5‐dimethylbenzoyl)‐2,3‐dihydro‐1,4‐benzodioxine‐6‐carbohydrazide showed high insecticidal activities, superior to that of ( 1 ) and equal to that of the commercial insecticide tebufenozide (RH‐5992). © 2002 Society of Chemical Industry