Five new organotin(IV) complexes of <i>ortho</i>-vanillin-2-hydrazinopyridine hydrazone with formula [R<sub>n</sub>SnCl<sub>4–n</sub>(VHP)] [R = Me<sub>2</sub>, n = 2 (2); R = Ph<sub>2</sub>, n = 2 (3); R= <i>n</i>Bu<sub>2</sub>, n = 2 (4); R = <i>n</i>Bu, n = 2 (5) and R = 1, n = 0 (6)] have been synthesized by direct reaction of ortho-vanillin-2-hydrazinopyridine hydrazone [(VHP), (1)], base and organotin(IV) chloride(s) in absolute methanol. The hydrazone ligand [(VHP), (1)] and its organotin(IV) complexes (2-6) have been characterized by UV-Visible, FT-IR and <sup>1</sup>H NMR spectral studies. Spectroscopic data suggested that in the complexes (2-4), the ligand (1) acted as a neutral bidentate ligand and is coordinated to the tin(IV) atom <i>via</i> the azomethine nitrogen and pyridyl nitrogen atoms, whereas the ligand (1) acted as a uninegative tridentate ligand and coordinated to the tin(IV) atom through phenolic-O, azomethine-N and pyridyl-N atoms in complexes (5-6). The toxicity of the ligand (1) and its organotin (IV) complexes (2-6) were determined against <i>Artemia salina</i>. Organotin(IV) complexes showed moderate activity against <i>Artemia salina</i>. The ligand (1) and its organotin(IV) complexes (2-6) were also tested against four types of bacteria namely <i>Bacillus cereus</i>, <i>Staphylococcus aureus</i>, <i>Escherichia coli</i> and <i>Enterobacter aerogenes</i>. All organotin(IV) complexes and the free ligand (1) showed better antibacterial activities against bacteria. Among the organotin(IV) complexes (2-6), diphenyltin(IV) complex (3) showed higher activity against the four types of bacteria