Enhanced Anti-Fungal Activity of the Organo-Soluble Borate Ester, Tetra-n-butylammonium Bis(ortho-hydroxymethylphenolato)borate
Jenny M. Carr A , Peter J. Duggan B C F , David G. Humphrey A F and Edward M. Tyndall D EA CSIRO Forestry and Forest Products, Clayton South VIC 3169, Australia.
B School of Chemistry, Monash University, Melbourne VIC 3800, Australia.
C CSIRO Molecular Science, Clayton South VIC 3169, Australia.
D Centre for Green Chemistry, Monash University, Melbourne VIC 3800, Australia.
E Present address: Biota Holdings Ltd, 10/585 Blackburn Rd, Notting Hill VIC 3168, Australia.
F Corresponding authors. Email: peter.duggan@csiro.au, david.humphrey@csiro.au
Australian Journal of Chemistry 58(1) 21-25 https://doi.org/10.1071/CH04247
Submitted: 26 October 2004 Accepted: 1 December 2004 Published: 14 January 2005
Abstract
The borate ester, tetra-n-butylammonium bis(ortho-hydroxymethylphenolato)borate, NBu4[B(o-hmp)2], was synthesized and characterized by NMR spectroscopy (1H, 13C, 11B), ES-MS, and X-ray crystallography. The anti-fungal activity of this compound, as well as its sodium salt, the parent phenol, tetra-n-butylammonium bromide, and boric acid were evaluated against two wood decay fungi. The tetraalkylammonium borate NBu4[B(o-hmp)2] shows the highest activity out of the compounds examined. This finding suggests that the formation of lipophilic borate esters is a promising approach for the development of leach-resistant, borate-based wood preservatives.
Acknowledgements
This work was funded by the Australian Research Council, Monash University, and CSIRO Forestry and Forest Products. E.M.T. is a recipient of an Australian Postgraduate Award.
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* For example, 5-halo-4-alkyl-2-hydroxymethylphenol, where halo = Cl or Br; alkyl = n-nonyl.
† In bioassays of this type, concentrations are commonly expressed as μmol per unit area rather than μmol per unit volume.
