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Studies in aryltin chemistry: part 7. Spectroscopic and fungicidal studies of some p ‐substituted tri‐aryltin acetates, oxides and hydroxides
Author(s) -
Wharf I.,
Lamparski H.,
Reeleder R.
Publication year - 1997
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/(sici)1099-0739(199712)11:12<969::aid-aoc660>3.0.co;2-5
Subject(s) - chemistry , moiety , mucor , botrytis cinerea , trigonal bipyramidal molecular geometry , stereochemistry , aspergillus niger , medicinal chemistry , organic chemistry , penicillium , molecule , biochemistry , botany , food science , biology
The fungicidal activity of a series of aryltin compounds, ( p ‐ZC 6 H 4 ) 3 SnX (X=OAc, OH, or 1/2O), where Z=F, Cl, CH 3 , CH 3 O, C 2 H 5 or (CH 3 ) 3 C, and for which IR and NMR ( 119 Sn) data are reported, has been assessed by radial growth assays on Aspergillus niger, Botrytis cinera, Mucor hiemalis, Fusarium solani and Penicillium chrysogenum , and the results compared with those for the Ph 3 SnOAc and Ph 3 SnOH archetypes. In most cases, para ‐substitution only slightly reduces biocidal activity, but with p ‐CH 3 O the aryltin is completely ineffective. This result correlates with the seemingly decreased ability of the ‘( p ‐CH 3 OC 6 H 4 ) 3 Sn’ moiety to achieve a trigonal‐bipyramidal five‐coordinate geometry with oxygen atoms in the axial positions, all other Ar 3 SnOAc and Ar 3 SnOH having this geometry in the solid state. A model for fungicidal action is proposed based on the need for the organotin inhibitor to attain the above geometry in the active site that it occupies in the ATPase enzyme, being the required condition for its biological activity. © 1997 John Wiley & Sons, Ltd.