The crystal structure of 1,2-dibenzoyl-1-tert-butylhydrazine, a nonsteroidal ecdysone agonist, and its effects on spruce budworm (Choristoneurafumiferana)

Abstract

The crystal structure of 1,2-dibenzoyl-1-tert-butylhydrazine (1), a nonsteroidal ecdysone agonist, has been established by direct methods and refined to a final R value of 0.038 for 2502 observed reflections. The crystals belong to the monoclinic system, a = 10.5114(7), b = 31.557(3), c = 11.1578(8) Å, β = 113.210(6)°, and the space group is P21/n. The N—N bond in 1 was found to adopt a gauche conformation with a dihedral angle of −71.8° or −58.1°. The two amide functions adopt different planar conformations. The compound is found to have a potent effect on the development of spruce budworm (Choristoneurafumiferana) larvae, causing early apolysis and subsequent mortality at 0.2–10 ppm concentration in artificial diet. Keywords: ecdysone, agonist, spruce budworm, 1,2-dibenzoyl-1-tert-butylhydrazine.