Straightforward synthesis of 2-chloro-N-(5-(cyanomethyl)-1,3,4-thiadiazol-2-yl)benzamide as a precursor for synthesis of novel heterocyclic compounds with insecticidal activity

Abstract

The current work is devoted to the synthesis of 2-chloro-N-(5-(cyanomethyl)-1,3,4-thiadiazol-2-yl)benzamide 5 by an efficient synthetic methodology. The authors decided to exploit the reactivity of cyanomethylene functionality to construct new heterocycles hybrid with 1,3,4-thiadiazole moiety. These compounds have been structurally characterized with the aid of elemental analysis and spectroscopic techniques such as IR, ¹H and ¹³C NMR and mass spectra. The synthesized compounds were evaluated for the insecticidal activity against cotton leaf worm (spodoptera littoralis). Among of them, compounds 7, 10, 12 and 17 showed much higher insecticidal activity. In particular, compound 12 exhibited the highest insecticidal activity.

Graphical Abstract

Keywords:

• Aryl isothiocyanate
• cyanoacetohydrazide
• cyanomethylene moiety
• insecticidal activity
• 1,3,4-thiadiazole