Structure–activity studies on the fungitoxicity of some triorganotin(IV) compounds

A. J. Kuthubtheen, R Wickneswari V Ratnam, V. G Kumar Das

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Seventeen triorganotin(IV) compounds, with the general formula R3SnX, containing symmetrical and unsymmetrical combinations of alkyl and aryl groups on tin and with a wide variation in the non‐carbon‐bonded anionic (X) residues, were examined along with three formally pentacoordinated adducts of triaryltin chlorides with triphenylphosphine oxide for their antifungal activity against nine plant pathogenic and saprophytic fungi. The in vitro tests included inhibitory studies on radial growth, mycelial growth, spore germination, and germ tube elongation. A significant finding was the dependence of fungitoxicity on the nature of the X group in both the tributyltin and triaryltin series, in contrast to earlier published reports on the negligible influence of the X groups on overall toxicity relative to the R group. This suggests that the X group is significantly involved in transporting the biocide to the reactive sites, and that the X group which tends to confer increased solubility to the triorganotin compound gives rise to increased activity. In studies of R group variations, tri‐iso‐butyltin bromide was found to be much less fungitoxic than tri‐n‐butyltin compounds, a result which is reconcilable in terms of increased steric encumbrance at the tin site in the former case. The steric factor is also implicated in the reduced activities observed for tris(p‐tolyl)tin and tris(p‐chlorophenyl)tin compounds relative to (Ph3SnX) towards most of the fungi screened in this study. In general, it was also noted that the triaryltins were more selective in their antifungal action than the trialkyltins, which exhibited broad spectral activity when applied at the concentration level of 10 μg cm−3.

Original languageEnglish
Pages (from-to)231-242
Number of pages12
JournalApplied Organometallic Chemistry
Volume3
Issue number3
DOIs
Publication statusPublished - 1989
Externally publishedYes

Fingerprint

Tin
Fungi
Tin Compounds
Disinfectants
Bromides
Toxicity
Chlorides
Elongation
Solubility

Keywords

  • fungitoxicity
  • Organotins
  • structure–activity relationships
  • trialkyltins
  • triaryltins

ASJC Scopus subject areas

  • Chemistry(all)
  • Inorganic Chemistry

Cite this

Structure–activity studies on the fungitoxicity of some triorganotin(IV) compounds. / Kuthubtheen, A. J.; V Ratnam, R Wickneswari; Das, V. G Kumar.

In: Applied Organometallic Chemistry, Vol. 3, No. 3, 1989, p. 231-242.

Research output: Contribution to journalArticle

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