Synthesis, structure and biological activities of novel triazole compounds containing 2-methylidenethiazolidine ring

Abstract

The two compounds 1-[1-(2′,4′-dichlorobenzoyl)-1-(3- phenylthiazolidin-2-ylidene)methyl]-1,2,4-triazole (3a) and 1-[1-(4′- fluorobenzoyl)-1-(3-phenylthiazolidin-2-ylidene)methyl]-1,2,4-triazole (3b) were prepared by reaction of phenyl isothiocyanate, 1,2-dibromoethane with α-(1,2,4-triazol-1-yl)-substituted-acetylbenzene. Their structures were identified by means of elemental analysis, IR, and 1H NMR spectra. The single crystal of compound 3b was also obtained. It crystallizes in triclinic system with space group P1 and a=0.9390(2) nm, b=0.9661(2) nm, c= 1.0929(2) nm, α=111.53(3)°, β=100.46(3)°, γ=102.08(3)°, Z=2, V=0.8647(3) nm3, Dc=1.407 g/cm3, μ=0.213 mm-1, F(000)=380, final R 1=0.073. There is obvious potentially weak C - H⋯Y (Y=N, F, O) intermolecular interaction between the molecules in the crystal lattice, which stabilizes the crystal structure. The result of the biological test showed that the two compounds have certain fungicidal activities. © 2005 SIOC, CAS, & Wiley-VCH Verlag GmbH & Co. KGaA.