Synthesis, characterization and biocidal studies of new ferrocenyl thiadiazolo-triazinone complexes

• Published in: Applied organometallic chemistry Vol. 20; no. 8; pp. 505 - 511
• Main Authors: El-shiekh, Said M., Abd-Elzaher, Mokhles M., Eweis, Mohamed
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.08.2006; Wiley
• Subjects: Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; biocidal activity; Biological and medical sciences; diacetylferrocene; General aspects; magnetic properties; Medical sciences; Pharmacology. Drug treatments; thiadiazolo-triazinone; Sulfur nitrogen heterocycle; Organic ligand; Acetate; Transition metal Complexes; biocidal activity; In vitro; Metallocene; Physical properties; Antimicrobial agent; Characterization; diacetylferrocene; Iron Organic compounds; Antifungal agent; Cyclization; Structure activity relation; Carboxylate; Bicyclic compound; thiadiazolo-triazinone; Antibacterial agent; Chemical synthesis; Magnetic properties
• ISSN: 0268-2605; 1099-0739
• DOI: 10.1002/aoc.1100

One‐pot synthesis of ferrocenyl ligand, 1,1′‐bis[1,5‐methyl‐4H‐(1,3,4)‐thiadiazolo(2,3‐c)(1,2,4)triazin‐4‐one]ferrocene was prepared from the reaction of 1,1′‐diacetylferrocene with 4‐amino‐2,3‐dihydro‐6‐methyl‐3‐thioxo[1,2,4]triazin‐5(4H)one. The ligand, L, forms 1:1 complexes with Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) in good yield. Characterization of the ligand and its complexes was carried out using IR, 1H NMR, magnetic susceptibility as well as elemental analysis. Biocidal activity of the ligand and its complexes were determined against the standard fungal strains of Aspergillus niger, Cladosporium herbarum and Fusarium moniliforme using the paper disc diffusion method; and against bacterial strains of Escherichia coli and Staphylococcus aureus using viable cell counting technique. The results indicated that the complexes are biologically more active than the free ligand. The biocidal activity depends on the metal ion, concentration as well as the tested fungi and bacteria. Copyright © 2006 John Wiley & Sons, Ltd. The ferrocenyl ligand L, 1,1′‐bis[1,5‐methyl‐4H‐(1,3,4)‐thiadiazolo(2,3‐c)(1,2,4)triazin‐4‐one]ferrocene, was prepared from the reaction of 1,1′‐diacetylferrocene with 4‐amino‐2,3‐dihydro‐6‐methyl‐3‐thioxo[1,2,4]triazin‐5(4H)one. The ligand L forms 1:1 complexes with Mn(II), Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) in good yields. Studies of the biocidal activity of the ligand and its complexes carried out against standard strains of Aspergillus niger, Cladosporium herbarum, Fusarium moniliforme, Escherichia coli and Staphylococcus aureus indicate that the complexes are biologically more active than the free ligand.