Enhanced Anti-Fungal Activity of the Organo-Soluble Borate Ester, Tetra-n-butylammonium Bis(ortho-hydroxymethylphenolato)borate

2005 ◽  
Vol 58 (1) ◽  
pp. 21 ◽  
Author(s):  
Jenny M. Carr ◽  
Peter J. Duggan ◽  
David G. Humphrey ◽  
Edward M. Tyndall
Keyword(s):  
Nmr Spectroscopy ◽  
Wood Decay ◽  
Wood Preservatives ◽  
Decay Fungi ◽  
X Ray ◽  
X Ray Crystallography ◽  
Fungal Activity ◽  
Wood Decay Fungi ◽  
Borate Ester ◽  
Anti Fungal

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.

Quaternary Ammonium Arylspiroborate Esters as Organo-Soluble, Environmentally Benign Wood Protectants

2005 ◽  
Vol 58 (12) ◽  
pp. 901 ◽  
Author(s):  
Jenny M. Carr ◽  
Peter J. Duggan ◽  
David G. Humphrey ◽  
James A. Platts ◽  
Edward M. Tyndall
Keyword(s):  
Boric Acid ◽  
Wood Decay ◽  
Environmentally Benign ◽  
Wood Preservatives ◽  
Decay Fungi ◽  
Wood Decay Fungi ◽  
Test Organisms ◽  
11B Nmr ◽  
The Stability ◽  
Anti Fungal

As part of a larger project aimed at the development of leach resistant boron-based wood preservatives, the anti-fungal and termiticidal activities, and the resistance to leaching from timber, of three related tetra-n-butylammonium spiroborates, tetra-n-butylammonium bis(ortho-hydroxymethylphenolato)borate 2, tetra-n-butylammonium bis[catecholato(2–)-O,O′]borate 3, and tetra-n-butylammonium bis[salicylato(2−)-O,O']borate 4, have been examined. All three borates are found to be active against test organisms, with the following orders of activity being observed: 2 > 3 > 4 > boric acid against wood decay fungi, and 2 > 3 ≈ 4 > boric acid against termites. The most active compound in both assays 2 also has the highest calculated lipophilicity. In a test for permanence in wood, the following order of leach resistance is observed: 4 >> 3 ≈ 2 > boric acid. This order appears to correlate more closely with the stability constants of the borate esters, as determined using 11B NMR spectroscopy, rather than calculated lipophilicities.

Cupressus macrocarpa Heartwood Oil and its Bioactivity against some Wood Decay Fungi

2012 ◽  
Vol 485 ◽  
pp. 413-416 ◽  
Author(s):  
Li Jun Zhang ◽  
Yuan Yuan Zhang ◽  
Shu Jun Li ◽  
J.J. Karchesy
Keyword(s):  
Steam Distillation ◽  
Wood Decay ◽  
Irpex Lacteus ◽  
Decay Fungi ◽  
Filter Paper Disc ◽  
Postia Placenta ◽  
Fungal Activity ◽  
Wood Decay Fungi ◽  
Anti Fungal ◽  
Paper Disc

Cupressus macrocarpa (Monterey cypress) heartwood has natural durability. The heartwood oil was prepared by steam distillation and its anti-fungal activity was tested against four wood decay fungi, i.e. Trametes versicolor, Irpex lacteus, Gloeophyllum trabeum, and Postia placenta with a filter paper disc method. The oil was active against all these fungi at the concentration of 8 mg.mL-1 or greater, but Postia placenta was the most difficult for the oil to inhibit. GC-MS was adopted to analyze the components of the heartwood oil. Two components, 4-terpineol and carvacrol were identified and carvacrol represented 94.428% of the oil. The oil had anti-fungal activity mostly because of carvacrol in the high content

Synthesis of N-(3-Rosin Acyloxy-2-Hydroxyl) Propyl-N,N Diethanolamine and its Anti-Fungal Activity

2011 ◽  
Vol 280 ◽  
pp. 124-127 ◽  
Author(s):  
Tao Liang ◽  
Shuang Yue Li ◽  
Shu Jun Li ◽  
Li Jun Zhang
Keyword(s):  
Chemical Structure ◽  
Wood Decay ◽  
Raw Material ◽  
Liquid Chromatography Mass Spectrometry ◽  
Decay Fungi ◽  
Fungal Activity ◽  
Amide Derivative ◽  
Wood Decay Fungi ◽  
Anti Fungal

Rosin was used as a raw material to prepare N-(3-rosin acyloxy-2-hydroxyl) propyl-N,N diethanolamine. First, rosin was modified with epoxy chloropropane. Then the modified rosin reacted with diethanolamine and N-(3-rosin acyloxy-2-hydroxyl) propyl-N, N diethanolamine was produced under the following conditions: modified rosin and diethanolamine mole ratio of 1:2, reaction temperature of 78°C, and reaction time of 2.5 h. The chemical structure of the product as a rosin amide derivative was identified by Fourier transform infrared spectroscopy (FTIR) and liquid chromatography-mass spectrometry (LC-MS) method. The anti-fungal activity of this rosinyl tertiary amine was determined in vitro against wood decay fungi, Trametes versicolor, Gloeophyllum trabeum and mould fungi, Aspergillus niger and Paecilomyces variot Bainier. The anti-fungal experiment results signified that N-(3-rosin acyloxy-2-hydroxyl) propyl-N,N diethanolamine was active to these fungi at a certain concentration.

Resistance of bioincised wood treated with wood preservatives to blue-stain and wood-decay fungi

2011 ◽  
Vol 65 (1) ◽  
pp. 108-115 ◽  
Author(s):  
M. Schubert ◽  
T. Volkmer ◽  
C. Lehringer ◽  
F.W.M.R. Schwarze
Keyword(s):  
Wood Decay ◽  
Wood Preservatives ◽  
Decay Fungi ◽  
Wood Decay Fungi ◽  
Blue Stain

Synthesis of a Rosin Amide and Its Inhibition of Wood Decay Fungi

2010 ◽  
Vol 113-116 ◽  
pp. 2232-2236 ◽  
Author(s):  
Jian Li ◽  
Shuang Yue Li ◽  
Shu Jun Li ◽  
Jing Wang ◽  
Dan Liu
Keyword(s):  
Aspergillus Niger ◽  
Weight Ratio ◽  
Wood Decay ◽  
Raw Material ◽  
Nuclear Magnetic Resonance Analysis ◽  
Ionization Mass ◽  
Decay Fungi ◽  
Amide Derivative ◽  
Wood Decay Fungi ◽  
Anti Fungal

Rosin was used as raw material to prepare a rosin amide derivative. First, rosin was modified by acrylic acid with the weight ratio of 4.5:1. Then the modified rosin was reacted with diethyltriamine and the rosin amide derivative was produced under the following conditions: modified rosin and diethyltriamine mole ratio of 1:3.5, dimethylbenzene as water carrying agent, reaction temperature of 160-180 °C, and reaction time of 8h. The chemical structure of the product as a rosin amide derivative was identified by Fourier transform infrared spectroscopy, electrospray ionization-mass spectrometry, and 1H nuclear magnetic resonance analysis. The anti-fungal activity of the derivative was determined in vitro with wood decay fungi such as Aspergillus niger, Paecilomyces variotii, Trametes versicolor and Gloeophyllum trabeum. The anti-fungal experiment results signified that the derivative is active vs. these fungi, but less effective with Aspergillus niger. Since it is produced easily from rosin, which is renewable and not expensive, this rosin amide could be a potential wood preservative.

Fungi colonizing preservative-treated Douglas-fir poles after remedial treatment with fumigants

1989 ◽  
Vol 35 (2) ◽  
pp. 283-288 ◽  
Author(s):  
Magdalena Y. Giron ◽  
Jeffrey J. Morrell
Keyword(s):  
Treated Wood ◽  
Wood Decay ◽  
Douglas Fir ◽  
Wood Preservatives ◽  
Nutrient Media ◽  
Trichoderma Spp ◽  
Decay Fungi ◽  
Wood Decay Fungi ◽  
Fungal Populations

The microfungi present in transmission poles of preservative-treated Douglas-fir remedially treated with one of four fumigants were determined by removing increment cores 5 and 15 years later and culturing them on nutrient media. The microfungi isolated from the wood were then characterized according to their ability to cause a loss in wood weight, to tolerate conventional wood preservatives, and to tolerate wood fumigants. The wood treated with fumigants 5 years earlier was sparsely colonized, while that treated 15 years earlier was colonized more heavily. In general, many of the same species of microfungi occurred in treated and untreated poles. In both, fungal populations were dominated by Scytalidium and Trichoderma spp. None of the isolates caused losses in wood weight greater than 5%, but several exhibited tolerance to short fumigant exposures. The latter trait may help explain the presence of these fungi in wood still containing measurable levels of fumigant. The presence in fumigant-treated wood of fungi previously shown to be antagonistic toward wood decay fungi may help explain the ability of the four test fumigants to provide long-term protection.Key words: fungi, Scytalidium, Trichoderma, colonization, Douglas-fir.

scholarly journals Rapid Dye Decolorization Method for Screening Potential Wood Preservatives

2000 ◽  
Vol 66 (12) ◽  
pp. 5457-5459 ◽  
Author(s):  
Olga Borokhov ◽  
Stephen Rothenburger
Keyword(s):  
Direct Observation ◽  
Agar Medium ◽  
Screening Method ◽  
Wood Decay ◽  
Dye Decolorization ◽  
Wood Preservatives ◽  
Inhibitory Effects ◽  
Decay Fungi ◽  
Wood Decay Fungi ◽  
Oxidative Agents

ABSTRACT We developed a new screening method for potential wood preservatives based on decolorization of the dye Remazol Brilliant Blue R by extracellular oxidative agents produced by wood decay fungi. Oxidative biodegradation of lignin yielded decolorized zones around and under fungal cultures on a dyed agar medium. Inhibitory effects were detected by direct observation and measurement of the decolorized zones.

scholarly journals Structure-activity relationships of cadinane-type sesquiterpene derivatives against wood-decay fungi

Holzforschung ◽  
2005 ◽  
Vol 59 (6) ◽  
pp. 620-627 ◽  
Author(s):  
Chi-Lin Wu ◽  
Shih-Chang Chien ◽  
Sheng-Yang Wang ◽  
Yueh-Hsiung Kuo ◽  
Shang-Tzen Chang
Keyword(s):  
Antifungal Activity ◽  
Wide Spectrum ◽  
Wood Decay ◽  
Wood Preservatives ◽  
Decay Fungi ◽  
Structure Activity Relationships ◽  
Chemical Structures ◽  
Structure Activity ◽  
Wood Decay Fungi

Abstract Cadinane-type sesquiterpenes have a wide spectrum of biological activity, but their use as wood preservatives and the structure-activity relationships of their derivatives have not yet been reported. A total of 13 compounds were synthesized from T-cadinol, T-muurolol, and α-cadinol and their chemical structures were confirmed by IR, MS, and 1H and 13C NMR. The antifungal properties of 16 compounds against three wood-decay fungi were evaluated in vitro. α-Cadinol showed strong antifungal activity against Lenzites betulina, Trametes versicolor, and Laetiporus sulphureus (total mean IC50 0.10 mM). Among the derivatives synthesized, 3β-ethoxy-T-muurolol (0.24 mM), 4ξH-cadinan-10β-ol (0.25 mM), 4ξH-muurolan-10β-ol (0.29 mM), and 4ξH-cadinan-10α-ol (0.25 mM) showed good antifungal activity against all fungi tested. Correlation was observed between the antifungal activity of the compounds tested and log P. Furthermore, the presence of an unsaturated double bond and oxygen-containing functional groups in the compounds plays a key role in their antifungal activity. The stereo configuration of cadinane-type sesquiterpenes also influences their antifungal activity. Understanding how the structure of natural compounds relates to their antifungal function is important and may facilitate their application as novel wood preservatives.

Synthesis and Characterization of BisN-(3-rosin acyloxy-2-hydroxyl) propyl-N,N dimethylamine

2010 ◽  
Vol 113-116 ◽  
pp. 2197-2200 ◽  
Author(s):  
Shuang Yue Li ◽  
Jing Wang ◽  
Shu Jun Li ◽  
Zhi Jun Chen ◽  
Bing Tian ◽  
...  
Keyword(s):  
Aspergillus Niger ◽  
Chemical Structure ◽  
Wood Decay ◽  
Wood Preservative ◽  
Gloeophyllum Trabeum ◽  
Decay Fungi ◽  
Wood Decay Fungi ◽  
Anti Fungal ◽  
Paper Disc

An anti-fungal derivative of rosin was synthesized. First, rosin was modified by acrylic acid and the modified rosin was esterified by epoxy chloropropane with the mole ratio of 1:3 for 3.5h at 90°C. The intermediate was bis 3-rosin acyloxy-2- hydroxypropyl chlorine and the degree of esterification was 98.81%. Then, bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N,N dimethylamine was made from the intermediate under the following conditions: the intermediate and dimethylamine mole ratio of 1:2, reaction temperature of 80°C and reaction time of 2.5h. The chemical structure of the product was identified by Fourier transform infrared spectroscopy (FTIR). The anti-fungal activity of the product was determined by paper-disc method with wood decay fungi such as Trametes versicolor, Gloeophyllum trabeum and wood stain fungi such as Aspergillus niger and Paecilomyces variot Bainier. The anti-fungal experiment results signified that bisN-(3-rosin acyloxy-2-hydroxyl) propyl-N, N dimethylamine is active vs. these fungi, but less effective with Aspergillus niger. Since it is produced easily from rosin, which is renewable and not expensive, this product has a promising future as a potential wood preservative.

Polyamidoamines (PAAs) functionalized with siloxanes as wood preservatives against fungi and insects

Holzforschung ◽  
2017 ◽  
Vol 71 (1) ◽  
pp. 65-75 ◽  
Author(s):  
Laura Bergamonti ◽  
Alessia Berzolla ◽  
Elisabetta Chiappini ◽  
Elisabetta Feci ◽  
Lara Maistrello ◽  
...  
Keyword(s):  
Wood Decay ◽  
Subterranean Termite ◽  
Wood Preservatives ◽  
Decay Fungi ◽  
Molar Ratios ◽  
Poria Placenta ◽  
Wood Decay Fungi ◽  
Ft Ir ◽  
Stegobium Paniceum ◽  
Nucleophile Addition

Abstract A novel treatment based on polyamidoamines (PAAs) for the preservation of wood against fungi and insects with a broad protection functionality, low effective concentration, and low environmental impact has been developed. PAAs were synthesized by nucleophile addition of ethanolamine (EtA) and/or 3-aminopropyltriethoxysilane (APTES) to N,N′-methylene-bisacrylamide (MBA). The molar ratios in the tested formulation were: I) MBA:EtA=1:1; II) MBA:APTES=1:1; III) MBA:EtA:APTES=1:0.5:0.5. These formulations, characterized by ESI-MS, NMR, FT-IR, were tested against: (a) the wood decay fungi (Coniophora puteana, Coriolus versicolor, and Poria placenta); (b) the subterranean termite Reticulitermes lucifugus, and the drywood termite Kalotermes flavicollis; (c) the woodborer Stegobium paniceum. Tests in combination with leaching showed that formulation II and III can be utilized as fungal wood preservatives for use classes 2–3 (EN 335:2013). In addition, all PAAs formulations were equally effective in preserving wood against the subterranean termite, and formulation II was most effective against drywood termite. On the other hand, the formulation I showed good efficacy against S. paniceum.

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