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Structure-activity relationships of fungicidal acetylenic sulphones

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Author: Selling, H.A. · Tempel, A.
Institution: Organisch Chemisch Instituut TNO
Source:Pesticide science, 7, 19-29
Identifier: 355345
doi: doi:10.1002/ps.2780070104
Keywords: Biology


Regression analysis in the l‐alkylsulphonyl‐2‐arylacetylene series yielded significant correlations of antifungal activity against six microorganisms with certain physicochemical parameters (electronic effects, lipophilicity and steric factors). Fungicidal activity is enhanced by introducing electron‐withdrawing substituents in the aryl nucleus, whereas variation of the lipophilic parameter reveals an optimum value. The results obtained indicate a mechanism of action based on a reaction of the compounds with nucleophiles present in the fungal cells, which was confirmed by determining the second‐order rate constants of the reaction between 1 ‐alkylsulphonyl‐2‐arylacetylenes and the model nucleophile 4‐nitro(thiophenol). The lipophilic para‐meter was also determined experimentally using thin‐layer chromatography. Regression analysis with this completely experimental set of parameters regression gave highly significant results in close agreement with those obtained above