T.H. Fisher, Y. Jin, T.P. Schultz
Fungicidal Activity of 3'-Substituted-3-Stilbenols
Summary
Twenty 3?-substituted-3-stilbenols were synthesized and tested for fungicidal activity (agar plate IC50
values) against two brown-rot fungi rot Gloeophyllum trabeum and Postia placenta and one white-rot
fungus Trametes versicolor. Compounds synthesized were eight trans-3-X-3?-stilbenols (X = OMe, Me,
Cl, OH, OPr, OBu, OOct, and O-p-Tol), three cis-3-X-3?-stilbenols (X = OMe, Me, Cl), three 3-hydroxy-?-(3-X-phenyl)cinnamic acids (X = OMe, Me, Cl), and six multisubstituted-3?-substituted-3-stilbenols (3?,4-diOMe, 3?-Me-4-OMe, 3?-Cl-4-OMe, 3?-OH-4-OMe, 3?-Cl-4-OMe-4?-OH, and 3?-Cl-4?-OH). The three cinnamic acids and 3?-OOct showed low to no activity against all three fungi. Most
of these 3?-substituted-3-stilbenols (15 of 20) had fungicidal activity against the white-rot fungus T. versicolor,
in contrast to earlier studies on 3?-substituted-4-stilbenols which were inactive against T. versicolor.
These 3?-substituted-3-stilbenols also had fungicidal activity against G. trabeum and P. placenta,
with the latter fungus having a parabolic lipophilic Quantitative Structure Activity Relationship (QSAR).
3?-O-p-Tol-3-stilbenol was the most active against T. versicolor and fifth most active against P. placenta
of the twenty 3?-substituted-3-stilbenols examined here.
Holzforschung, Walter de Gruyter
Print ISSN: 0018-3830
Volume: 55, 11/2001
Pages: 568 - 572
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