Synthesis, characterization and biological activity of diorganotin dithioate derivatives

Abstract

AbstractReaction of dithioacid (ArCS2CH2CO2H, Ar = phenyl, 2‐furyl or 2‐thienyl) with nBu2SnO gives monomeric (ArCS2CH2CO2)2Sn(Bun)2 in a 2:1 molar ratio, and dimeric {[(ArCS2CH2CO2)Sn(Bun)2]2O}2 in a 1:1 molar ratio, respectively, which have been characterized by IR, NMR (1H, 13C and 119Sn) spectra and elemental analyses. X‐ray crystal structure analyses indicate that the compound [(C4H3S)CS2CH2CO2]2Sn(Bun)2 is monomeric with the tin atom occupying a skew‐trapezoidal bipyramidal geometry. In addition, this compound forms a three‐dimensional structure through the weak intermolecular S…S and Sn…O interactions. Compound {[((C4H3S)CS2CH2CO2)Sn(Bun)2]2O}2 is a centrosymmetric dimer with a cyclic Sn2O2 unit, in which the coordination modes of the two crystallographically unique carboxylic ligands are different. One acts as monodentate ligand by the carboxylate oxygen atom, the other bridges two tin atoms via only one carboxylate oxygen atom. Furthermore, each tin atom in this compound locates a distorted trigonal bipyramidal geometry. Biological activities of these organotin compounds show that they have hardly acaricidal activity, but display certain activities on fungi. In mononuclear tin compounds, the inhibition percentage of [(C4H3S)CS2CH2CO2]2Sn(Bun)2 in vitro for Alternaria solani and Physolospora piricola is 57.1% and 43.9%, respectively, while in dimers {[((C4H3O)CS2CH2CO2)Sn(Bun)2]2O}2 shows high inhibition percentage for Gibbereila zeae (52.6%) and Physolospora piricola (50.0%), respectively. Copyright © 2006 John Wiley & Sons, Ltd.