Design and synthesis of diheterocyclic compounds containing tetrazolinone and 1,2,4-triazole

A novel series of 1-(4-chlorophenyl)-4-{[5-(alkylthio)-4-phenyl-4H-1,2,4-triazol-3-yl]methyl}-1,4-dihydro-5H-tetrazol-5-ones 6a-y were synthesized in good to excellent yields and their structures were identified by 1H nmr, 13C nmr, ms and elemental analysis. Determining the X-ray crystallography of compound 6j indicated that there were strong intermolecular hydrogen bonds in the stacking interactions. The bioassay results showed that compound 6k exhibited good insecticidal activities against T cinnabarinus at the dosage of 250 mg.L−1. To our knowledge, this is the first report about the insecticidal activity of tetrazolinone derivatives.