Structure–Activity relationships of effect of aryltin compounds onCeratocystis ulmi

Abstract

The effect of aryltin compounds (Ar,Sn and Ar,SnCI) on the growth of Ceratocystis ulmi, the causative agent of Dutch elm disease, was studied in shake culture. In all cases, the triaryltins were more effective than the tetra-aryltins as inhibitors of C. ulmi in vitro. Furthermore, substitution on the phenyl ring at the meta-and para-positions in the triaryltins did not have a major effect on the biocidal activity for the substituted triaryltins. Quantitative structure-activity relationships (QSARs) gave support to the idea that the species responsible for the inhibition of the fungus is the triaryltin cation. The QSARs further suggest that the interaction of the triaryltin cation with the fungal cell wall of C . ulmi is by a non-specific mechanism.

Synthesis, structural characterization, biological activity and thermal study of tri‐ and diorganotin(IV) complexes of Schiff base derived from 2‐aminomethylbenzimidazole

“…[35] Furthermore, it has been proposed for R 2 Sn(IV)-glycylglycinates (R = Me, n-Bu, n-Oct and Ph) on the basis of solution studies using several spectroscopic techniques, [36,37] that solvated species in aqueous solution or mixture of H 2 O and organic solvent and unsolvated species (mainly organic solvent) are present in equilibrium and contribute to the passage of alkyltin(IV) complexes across the cell membrane. [36,37] A quantitative structure-activity relation (QSAR) for a series of triaryltin(IV)/diorganotin(IV) complexes, Ph 3 SnXY/R 2 SnXY, [38,39] indicated that R 3 Sn + and R 2 Sn +2 are the causative agents and the XY group influences only the readiness of delivery of the active part, R 3 Sn + /R 2 Sn +2 into the cell. [40] Thus an attempt is being made to formulate the structure-activity correlation of the synthesized tri-and diorganotin(IV) complexes of Hsal-ambmz.…”

Studies in aryltin chemistry: part 7. Spectroscopic and fungicidal studies of somep-substituted tri-aryltin acetates, oxides and hydroxides

“…3b), which is inconsistent with the activity of [p-(CH 3 ) 3 CC 6 H 4 ] 3 SnCl against C. ulmi reported earlier. 13 However our bioassay method differs from that used by Eng et al and since all para-tbutyl aryltin compounds appear to have very low solubilities in many solvents, 16 our results may simply reflect the fact that the test compound, perhaps having precipitated out of the PDA medium during its preparation, would then not be available to the fungus.…”

“…[4][5][6] In contrast, structure-activity studies probing electronic and/or steric effects using substituents on the phenyl rings are relatively few, 5,[7][8][9][10][11][12] and only recently, while this work was reaching completion, was a study of the same type as this one reported. 13 This appeared to confirm that substitution on the phenyl rings at the para-position in triaryltins also does not seem to have any major effect on their biological activity.…”

“…(b) The systems chosen for study, Ar 3 SnOAc, Ar 3 SnOH and Ar 3 Sn) 2 O, are analogues of the commercial fungicides, 'Brestan' and 'Du-Ter', thus allowing a more direct comparison to be made with these compounds as well as avoiding the additional phytoxicity of the Ar 3 SnCl system 3 used in the earlier work. 13 …”

Toxicity of triorganotin compounds to the brine shrimp, Artemia salina

“…This type of explanation has been employed in explaining the antifungal activities of various triphenyltin compounds. [29][30][31][32] Examination of Table 3 indicates that, in general, the order of activity for the triorganotins against the brine shrimp is butyl b cyclohexyl b phenyl b …”