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Biocidal organotin compounds: Part 1. Preparation and characterization of triorganotin(IV) 4‐pyridyl‐ and 2‐pyrimidyl‐ thioacetates and the crystal structure of triphenyltin(2‐pyrimidylthioacetate)
Author(s) -
Chakrabarti A.,
Kamruddin Sk.,
Chattopadhyaya T. K.,
Roy A.,
Chakraborty B. N.,
Molloy K. C.,
Tiekink E. R. T.
Publication year - 1995
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590090409
Subject(s) - chemistry , trigonal bipyramidal molecular geometry , crystal structure , stereochemistry , tin , crystallography , medicinal chemistry , organic chemistry
The preparation and spectroscopic characterization of [R 3 Sn(O 2 CCH 2 SC 5 H 4 N‐4)], R == Ph, benzyl (Bz), cyclohexyl (c‐Hex) and n‐Bu, and of [R 3 Sn(O 2 CCH 2 SC 4 H 3 N 2 ‐2,6)], R == Me, Ph and n‐Bu, are reported. The 2‐pyrimidyl compounds feature trigonal bipyramidal tin centres with trans ‐R 3 SnO 2 geometries as was confirmed by X‐ray crystallography for [Ph 3 Sn(O 2 CCH 2 SC 4 H 3 N 2 ‐2,6)]. ¶ By contrast the 4‐pyridyl compounds have trigonal bipyramidal geometries in the solid state (arising from intermolecular Sn…N interaction) and tetrahedral geometries in solution. The biocidal activity of these compounds against the fungi Helminthosporium maydis (ITCC 2675) and H. oryzae (ITCC 2675), both of which damage crops such as maize and rice, shows promise. Encouraging is the observation that the compounds show no adverse phytotoxicity at concentrations to 10 −3 M.