A multicriteria ranking of organotin(IV) compounds with fungicidal properties

The application of multicriteria decision-making methods to the results of in vitro antifungal properties of organotin compounds of the type PhxSnXz (x = 2 or 3; X = O2CC6H4OH, O2CC6H4OCOCH3, Cl or O2CCH3; z = 1 or 2) and of free 2-hydroxybenzoic and 2-acetoxybenzoic acids against Aspergillus niger, Aspergillus flavus, Candida albicans, Penicillium citrinum, Trichophyton rubrum and Trichophyton violaceum have been described. Ranking information necessary to select one toxicant in preference to others and to assess the properties influencing the preference has been obtained. Patterns in the multivariate analyses suggest that cationic and anionic moieties of the toxicant play some roles in their fungicidal activities. The triphenyltin compounds were generally more active than their diphenyltin analogues, but the acetoxybenzoates were more active than the corresponding hydroxybenzoates, acetates or chlorides. Thus, triphenyltin acetoxybenzoate is up to 7.5 times as active as the corresponding acetate, which is commercially marketed as a fungicide. The results of the analyses have been discussed in the light of the mechanism of antifungal activity of organotin compounds and the potential of multivariate data analysis techniques to facilitate the screening and ranking of antifungal agents. Copyright © 2003 John Wiley & Sons, Ltd.

[1]  R. Singh,et al.  Studies of biologically potent organotin(IV) and organosilicon(IV) complexes of a sulfur donor ligand derived from 1‐acetylferrocene , 2002 .

[2]  J. Chollet,et al.  Antifungal effects of salicylic acid and other benzoic acid derivatives towards Eutypa lata: structure-activity relationship , 2002 .

[3]  Y. Ni,et al.  Spectrophotometric determination of metal ions in electroplating solutions in the presence of EDTA with the aid of multivariate calibration and artificial neural networks , 2002 .

[4]  Hugo Pastijn,et al.  Selecting land mine detection strategies by means of outranking MCDM techniques , 2002, Eur. J. Oper. Res..

[5]  J. Pierre Brans,et al.  Ethics and decision , 2002, Eur. J. Oper. Res..

[6]  R. K. Saxena,et al.  Novel synthetic approach for antifungal and antibacterial organotin compounds , 2000 .

[7]  S. Ado,et al.  Triphenyltin Salicylate-Antimicrobial Effect and Resistance - The Pyrophosphatase Connection , 2000, Journal of enzyme inhibition.

[8]  S. Kokot,et al.  Elemental content of Vietnamese rice. Part 2. Multivariate data analysis. , 1999, In Analysis.

[9]  H. Célis,et al.  Triphenyltin as an inhibitor of membrane-bound pyrophosphatase of Rhodospirillum rubrum. , 1998, Archives of biochemistry and biophysics.

[10]  A. Bacchi,et al.  Organotin complexes with pyrrole-2,5-dicarboxaldehyde bis(acylhydrazones). Synthesis, structure, antimicrobial activity and genotoxicity. , 1998, Journal of inorganic biochemistry.

[11]  I. Omae Applications of organometallic compounds , 1998 .

[12]  Brian W. Skelton,et al.  Triphenyltin(IV) compounds with biologically-active anionic groups: crystal and molecular structures of the p-ethoxybenzoic acid, acetylsalicylic acid, phthalic acid and salicylaldehyde derivatives , 1998 .

[13]  G. Eng,et al.  Fungicidal and spectral studies of some triphenyltin compounds , 1998 .

[14]  G. Ayoko,et al.  Synthesis and Antifungal Activity of Some Organotin(IV) Carboxylates , 1998, Metal-based drugs.

[15]  Eugène Chouraqui,et al.  Negotiation support systems: A multi-criteria and multi-agent approach , 1997 .

[16]  D. Vos,et al.  Synthesis, characteristic spectral studies and in vitro antimicrobial and antitumour activities of organotin(IV) complexes of Schiff bases derived from amino-acids , 1997 .

[17]  M. Nath,et al.  Spectral Studies and In Vitro Antimicrobial Activity of New Organotin(IV) Complexes of Schiff Bases Derived from Amino Acids , 1997 .

[18]  E. Tiekink,et al.  Synthesis, characterization and in vitro antitumour activity of triphenyl- and tri-n-butyltin benzoates, phenylacetates and cinnamates , 1997 .

[19]  B. D. James,et al.  Fungicidal Activity of Some Organotin Compounds against Ceratocystis ulmi , 1996 .

[20]  D. Clarke,et al.  Antifungal activity of halophenols and halonitrophenols , 1995 .

[21]  Bertrand Mareschal,et al.  The PROMCALC & GAIA decision support system for multicriteria decision aid , 1994, Decis. Support Syst..

[22]  G. Eng,et al.  Structure-activity relationships of effect of aryltin compounds on Ceratocystis ulmi , 1994 .

[23]  F. Zani,et al.  Synthesis, structure, antimicrobial, and genotoxic activities of organotin compounds with 2,6-diacetylpyridine nicotinoyl- and isonicotinoylhydrazones. , 1992, Journal of inorganic biochemistry.

[24]  H. R. Keller,et al.  Application of chemometrics for the selection of microwave digestion procedures , 1992 .

[25]  J. Cashion,et al.  Some triphenyltin(IV) complexes containing potentially bidentate, biologically active anionic groups , 1992 .

[26]  D. Vos,et al.  Exceptionally high in vitro antitumor activity of substituted triphenyltin benzoates including salicylates against a human mammary tumor, MCF‐7, and a colon carcinoma, WiDr , 1992 .

[27]  H. R. Keller,et al.  Microwave digestion: an analysis of procedures , 1992 .

[28]  A. Silvestri,et al.  Interactions of Organotins with Biological Systems , 1992 .

[29]  Jean Pierre Brans,et al.  Multicriteria decision making: A case study , 1991 .

[30]  F. Tanfani,et al.  Effect of the fungicides tributyltin acetate and tributyltin chloride on multilamellar liposomes: fluorescence studies. , 1991, Chemistry and physics of lipids.

[31]  M. Gielen Tin-based Antitumour Drugs , 1996, NATO ASI Series.

[32]  M. Meyerhoff,et al.  Salicylate-selective membrane electrode based on tin(IV) tetraphenylporphyrin. , 1989, Analytical chemistry.

[33]  R. Wickneswari,et al.  Changes in fungal and bacterial populations in soil treated with two triorganotin(IV) compounds , 1989 .

[34]  B. D. James,et al.  Inhibition of oxidative phosphorylation by organotin thiocarbamates. , 1989, Chemico-biological interactions.

[35]  S. Marshall,et al.  The toxicity of alkyllead compounds to Scrobicularia plana (Da Costa) , 1988 .

[36]  A. Crowe Organotin compounds in agriculture since 1980. Part I. Fungicidal, bactericidal and herbicidal properties , 1987 .

[37]  R. Hill,et al.  Triphenyltin substituted benzoates: A spectroscopic study of structure in solution and solid phases , 1986 .

[38]  H. Guard,et al.  Structure‐activity relationships for organotin compounds , 1985 .

[39]  Dietmar Seyferth,et al.  Comprehensive Organometallic Chemistry , 1984 .

[40]  Peter J. Smith,et al.  Structure‐activity relationships in triorganotin biocides: The influence of the anionic radical , 1984 .

[41]  W. Aldridge The Influence of Organotin Compounds on Mitochondrial Functions , 1976 .

[42]  M. Selwyn Triorganotin Compounds as Ionophores and Inhibitors of Ion Translocating ATPases , 1976 .

[43]  D. J. Drain,et al.  THE PREPARATION AND ANTIFUNGAL ACTIVITY OF SOME SALICYLIC ACID DERIVATIVES , 1957, The Journal of pharmacy and pharmacology.