1,2,4-Triazoles have been reported to associate with antimicrobial, fungicidal, anti-inflammatory, antiparasitic, insecticidal, herbicidal, antiviral, antitumor, anticonvulsant, antidepressant, hypotensive effects and plant growth regulatory activities. On the other hand, nitroimidazole like metronidazole, ornidazole, secnidazole and tinidazole are widely used in the treatment of diseases caused by protozoa and anaerobic bacteria. Furthermore, some 5-nitroimidazoles have been shown activity against Helicobacter pylori. In the design of new compounds, the development of hybride molecules through the combination of different pharmacophores in one frame may lead to compounds with increase antimicrobial activity. Herein, we have synthesized novel compounds containing (4-nitroimidazol-1yl)methyl fragment at the position 3 of the 4-substituted-1,2,4-triazole-5-thiones.

Six compounds were screened for their antimicrobial activity against reference strains of bacteria (9 species) and fungi (5 species). Two compounds inhibited the growth of Gram-positive Micrococcus luteus ATCC 10240 with MIC = 250 mg L^-1 and MIC = 500 mg L^-1, respectively. The most effective against Gram-negative bacteria was 4-phenyl-1-[(4-nitroimidazol-1-yl)acetyl]thiosemicarbazide with MIC = 500 mg L^-1 for E. coli ATCC 25922 and about 36 to 65% reduction of the growth of Klebsiella pneumoniae ATCC 13883 and Proteus mirabilis ATCC 12453 at lower concentrations (7.81 - 250 mg L^-1). None of the compounds had influence on the growth of reference strains belonging to Staphylococcus, Bacillus or Pseudomonas species. The tested compounds had no activity against fungi, besides 4-(4-tolyl)-1-[(4-nitroimidazol-1-yl)acetyl]thiosemicarbazide showing moderate inhibitory effect against Trichophyton menthagrophytes ATCC 9533 with MIC = 250 mg L^-1 and about 30-70% reduction of the growth of this dermatophyte at lower concentrations (7.81 - 125 mg L^-1). Moreover, this compound exerted about 0-70% inhibition of the growth of reference strains of Candida spp. and Aspergillus niger ATCC 16404 at concentrations of  7.81 - 500 mg L^-1.

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