AU641599B2 - Composition for protecting timber from fungal growth - Google Patents
Composition for protecting timber from fungal growth Download PDFInfo
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- AU641599B2 AU641599B2 AU29732/92A AU2973292A AU641599B2 AU 641599 B2 AU641599 B2 AU 641599B2 AU 29732/92 A AU29732/92 A AU 29732/92A AU 2973292 A AU2973292 A AU 2973292A AU 641599 B2 AU641599 B2 AU 641599B2
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- cnh2n
- timber
- alkali metal
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- 239000000203 mixture Substances 0.000 title claims description 52
- 230000002538 fungal effect Effects 0.000 title description 8
- -1 alkali metal salt Chemical class 0.000 claims description 43
- 241000233866 Fungi Species 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 7
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 3
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 3
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
- 229960002446 octanoic acid Drugs 0.000 claims description 3
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 210000002837 heart atrium Anatomy 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000003139 biocide Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 150000004714 phosphonium salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001339 alkali metal compounds Chemical class 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241001149956 Cladosporium herbarum Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241001515915 Ophiostoma piliferum Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000907561 Sydowia polyspora Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 229940124561 microbicide Drugs 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FRXLZEVXYFDHIM-UHFFFAOYSA-N phosphanium;hydrogen sulfate Chemical class [PH4+].OS([O-])(=O)=O FRXLZEVXYFDHIM-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- AKUNSPZHHSNFFX-UHFFFAOYSA-M tributyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC AKUNSPZHHSNFFX-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
Landscapes
- Chemical And Physical Treatments For Wood And The Like (AREA)
Description
F'IUU/Ul 1 2Vi5N1 Rogulation 3.2(2)
AUSTRALI
Patents Act 1990 j41
ORIGINAL
COMPLETE SPECIFICATION STANDARD PATENT Application Number: Lodged: *9 p p *3 pp 0
PG..
p p p. p. 0 p. p p G* Invention Title: COMPOSITION FOR PROTECTING TIMBER FROM FUNGAL GROWTH p.
p h P P
P.
The following statement is a full descriptlcn of this Invention, Including the best method of performing It known' to :-US COMPOSITION FOR PROTECTING TIMBER FROM FUNGAL GROWTH The present invention relates to a composition for protecting timber against growth by blue-stain fungi and mold fungi, to the use of said composition, and to a method of protecting timber against growth by bluestain fungi and mold fungi.
The fungi which infect timber are subdivided into the three groups comprising blue-stain fungi, mold fungi and rot fungi. Although blue-stain fungi and mold fungi do not cause rot, they do cause discolouration and are able to promote the growth of the fungi which rot wood (Basidiomycetes).
The most widely used control agent in this sector is still sodium pentachlorophenol. However, the use of this biocide is disputed on account of its presumed negative environmental impact. More recent V a..
compounds, such as methylenebisthiocyanate and 2'- 1 5 (thiocyanomethylthio)benzothiazole (TCMTB), have various serious shortcomings, including insolubility in water, temperature instability or corrosiveness. The most widely used product in the USA, Kopcoat NP-1®, comprising 64.8% of a quaternary ammonium compound and 7.6% of 3iodo-2-propynylbutylcarbamate (IPBC), also has the drawback that the IPBC component is poorly soluble in water, so that large amounts of the other biocide have to be used.
A useful biocide for controlling fungal growth on freshly sawn timber should be fully water-soluble so as to avoid any precipitation when dilutions are used or where adsorption on the wood varies. In addition, the 25 biocide should not cause discolouration of the wood or interfere with its further processing, and it must adhere to the surface of the wood with sufficient tenacity so as not to be washed off by, for example, rain.
Some of these requirements are met by quarternary ammonium salts which have long been used as wood preservatives Richardson, 3 0 Sapstain Control, Paperi ja puu Nr. 10, S. 613 (1972)]. The usefulness of aliphatic C 6 -C11 monocarboxylic acids is also known in this connection US-A-3 995 077 and US-A-4 380 561].
A synergistic composition comprising a quarternary ammonium compound and an alkali metal salt of an organic carboxylic acid is 3 5 disclosed in US-A-4 585 795 as a wood preservative for inhibiting growth -2 by blue-stain fungi and mold fungi. This composition is able to effect an enhanced action over that obtained by using the individual substances.
Quarternary phosphonium compounds are also known to have biocidal activity. Thus EP-A-332 578 teaches the use of a number of tetraalkylammonium and tetraall .Ihosphonium salts, including tri-n-butyln-tetradecyll hosphonium tetrafluoroborate, as biocides.
The activity of a number of tetraalkylphosphonium bromides and chlorides, including tri-n-butyl-n-tetradecylphosphonium chloride, as microbicides for water treatment is disclosed in US-A-4 874 526.
Surprisingly, it has now been found that the combination of a quarternary phosphonium compound with the salt of an organic carboxylic acid significantly enhances toxicity to fungi. The invention accordingly relates to a composition comprising such a combination which can be used with advantage for protecting timber, especially freshly sawn timber, 15 against growth by blue-stain fungi and mold fungi.
The novel composition is a mixture comprising at least one quaternary phosphonium compound of formula [(C4H9)3P CnH2n+l]+ Xor [(C4H9)3P CnH2n+112 S04 2 wherein n is an integer from 8 to 16 and X- is an anion selected from the group consisting of Cl-, Br", NO3and HSO4-, and at least one alkali metal salt of an aliphatic C6-C12 monocarboxylic acid.
S:o- The aliphatic C6-C12 monocarboxylic acid may be selected from the group consisting of capronic acid, heptanoic acid, caprylic acid, capric acid, lauric acid, 2-ethylhexanoic acid, 2-ethylheptanoic acid, and mixtures 25 of isomers such as isooctanoic acid or isononanoic acid.
Those compositions are preferred in which the aliphatic monocarboxylic acid is selected from the group consisting of 2ethylhexanoic acid, isononanoic acid, isooctanoic acid, 2-ethylheptanoic acid, heptanoic acid, capric acid and caprylic acid. Compositions containing 2-ethylhexanoic acid are especially preferred.
Particularly useful alkali metal salts are the sodium, potassium and lithium salts. The sodium and potassium salts are preferred, and the sodium salt is most preferred.
The alkali metal salt can be added per se to the novel composition.
3 5 Alternatively, the acid and the basic alkali metal compound which forms -3 the salt with the acid may also be added separately. In this latter case, a hydroxide carbonate or hydrogencarbonate of an alkali metal will conveniently be used, preferably an alkali metal hydroxide, such as NaOH.
Acid and alkali metal compound will preferably be added in equivalent amounts. An excess of one or other component can serve to adjust the pH to the desired value.
The butyl groups of the phosphonium compound may be straightchain or branched. n-Butyl is preferred.
The long chain alkyl group CnH2n+l of the phosphonium compound may also be straight-chain or branched. Typical examples of such groups include 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl or hexadecyl.
*J 15 The long chain alkyl groups may also be mixtures of isomers. Also possible are mixtures of alkyl groups of different chain length, for example if customary technical mixtures of alkyl halides and alcohols are used for the preparation of the phosphonium compounds.
Preferred compositions are those wherein the long chain alkyl group CnH2n+1 of the phosphonium compound contains from 10 to 16 carbon atoms and is preferably a dodecyl or a tetradecyl group. A tetradecyl group is especially preferred.
Also preferred are compositions in which the quaternary phosphonium compounds have the formula [(C4H9)3P CnH2n+]+CI.
25 Particularly preferred compositions are those wherein the phosphonium compound is tributylphosphoniumtetradecyl chloride.
It is especially advantageous to use the novel compositions for temporarily protecting freshly sawn timber, i.e. for inhibiting fungal growth until the timber is processed.
3 0 The invention likewise relates to compositions which, in addition to the aforementioned active ingredients, also contain conventional formulation auxiliaries. Preferred formulation auxiliaries are water, alcohols, free carboxylic acids, including the aliphatic monocarboxylic acids cited above, and/or bases. The compositions will preferably contain an alkali metal hydroxide as base, preferably NaOH. The alcohol will -4 conveniently be a CI-C4alkanol. A novel composition will typically be prepared by mixing 13.4 -14.5 of NaOH, 19 22% of water 48 52 of an aliphatic monocarboxylic acid 0 2 of an alcohol containing 2-4 carbon atoms, and 14 16 of a 50 aqueous solution of phosphonium compound. In tc above and throughout this specification, the percentages are by \aight, unless otherwise indicated. Particularly 1 0 preferred compositions are those wherein component is 2ethylhexanoic acid, component is isopropanol, and component is a ,solution of tributylphosphoniumtetradecyl chloride.
Some of the compounds used for the preparation of the composition, for example the phosphonium halide and the carboxylic acid 15 salt, are known and are commercially available.
The phosphonium compounds present in the novel compositions can be prepared in a manner known per se. The procedure typically comprises reacting appropriate phosphonium halides with salts, such as alkali metal salts, which contain the desired anions, to give the corresponding phosphonium salts of this invention in which X- is not a halide. Typically, sodium nitrate can be reacted with a quarternary phosphonium halide (C4H9)3P CnH2n+l Hal (Hal=halogen). The reaction conditions are not critical and the reaction can be carried out under normal pressure and at room temperature and with water as solvent.
S':i 25 Working up is also carried out by per se known methods, and the reaction products can be extracted with an organic solvent and obtained in pure form after removal of the solvent by distillation. Suitable solvents are dichloromethane or ethyl acetate. The starting materials are also known per se and some are commercial products.
Corresponding phosphonium hydrogensulfates can be obtained typically by reacting the rhodanides with concentrated sulfuric acid, accompanied by evolution of COS. Working up is then conveniently carried out by stirring in ice-water and thereafter stripping off volatile constituents under vacuum. The rhodanides may be obtained by the 3 5 method described above in connection with the nitrates.
The salt of the aliphatic monocarboxylic acid can be used either per se or formed from the corresponding free acid and a suitable alkali metal compound, such as an alkali metal hydroxide. The novel composition is conveniently obtained initially in the form of a concentrate with contains the phosphonium compound in a concentration of 1 to 40 by weight and the alkali metal carboxylate in a concentration of 10 to 90 by weight. The composition is conveniently prepared by mixing the individual components, preferably by dissolving the active ingredients (or their precursors, carboxylic acid and, preferably, alkali metal hydroxide in the case of the carboxylate) in water, with or without the addition of an alcohol.
The weight ratio of phosphonium compound:free carboxylic acid in the novel compositions is conveniently 1:1 to 1:50, preferably 1:4 to 1:10. The composition is preferably used in dilutions which contain 0.05 to 5% by weight, preferably 0.1 to 1.5% by weight, of the phosphonium compound.
1 5 The invention further relates to the use of the cited quaternary phosphonium compounds of formula [(C4H9)3P CnH2n+ll+ X- or [(C4H9)3P CnH2n+112+ S042- in combination with aikali metal salts or aliphatic C6-C1 2monocarboxylic acids for protecting timber against growth by blue-stain fungi and mold fungi. The use of aqueous solutions of the combination formulation is preferred.
The invention relates further to a process for protecting timber i against growth by blue-stain fungi and mold fungi, which comprises treating said timber with a solution of suspension which contains the :quaternary phosphonium compound of formula [(C4H9)3P CnH2n+l]+ X- 25 or [(C4H9)3P CnH2n+1l2+ S04 2 wherein n and X are as defined above, and an alkali metal salt of an aliphatic C6-C12monocarboxylic acid. A process which comprises the use of an aqueous solution is preferred. In the process of this invention, the timber to be protected is conveniently impregnated with a solution of both active ingredients. This can be done, 3 0 for example, by immersing the timber in, or spraying it, with the cited solution or solutions.
Use Example Tests for determining the protective action against fungal growth are 3 5 carried out using freshly sawn timber in accordance with NWPC Standard 1.4.1.3./79 (Nordic Wood Preservation Council, Mycological Testing of -6- Anti-stain Preservatives for Freshly Sawn Timber, the Mini-board Method, Sweden 1980). A novel formulation of the following composition is used: 13.9% of a NaOH, 20.3% of a water 50.0% of 2-ethylhexanoic acid 0.8% of isopropanol and 15.0% of a 50% solution of tributylphosphoniumtetradecyl chloride in water.
The solutions listed in Table 1 are prepared by diluting this concentrate with water.
One half of test pine boards (10 x 50 x 300 mm) is immersed for seconds in each solution, dried for 24 hours and inoculated with the 15 following mixed cultures: mixed culture of blue-stain fungi: Aureobasidium pullulans, J Sclerophoma pityophila, r Ceratocystis pilifera; mixed culture of mold fungi: Aspergillus niger, Cladosporium herbarum, Trichoderma viride.
t* Si S 25 The inoculated boards are incubated at room temperature. After 4 weeks the growth is compared on the treated and untreated sides and evaluated according to the following scale: 0 free from fungal growth 1 traces of growth 2 little growth 3 moderate growth 4 vigorous to maximum growth The results are reported in Table 1.
Table 1: Degree of fungal growth after 4 weeks. Comparison with/without the treatment of this invention (immersion in 4.0% and aqueous solution of the concentrate).
Percentage of Blue-stain growth Mold growth concentrate untreated treated untreated treated half half half half 3 0 3 0 4 0 4 0 It is evident from the table that the novel formulation affords excellent protection against growth by the mold and blue-stain fungi investigated in this test.
9 99r 9 *9 .9 *i .9 r *a4 a 9 '.9 9i 9r 9 9 99r
Claims (11)
1. A composition for protecting timber against growth by blue-stain fungi and mold fungi, comprising at least one quaternary phosphonium compound of formula [(C 4 H 9 3 P CnH 2 n+l]+X or [(0 4 H 9 3 P CnH2n+12+SO4 2 wherein n is an integer from 8 to 16 and X- is an anion selected from the group consisting of F, of CI-, BrC, N0 3 and HS0 4 and at least one alkali metal salt wan aliphatic C6-C12 monocarboxylic acid.
2. A composition according to claim 1, wherein the aliphatic monocarboxylic acid is selected from the group consisting of 2-ethylhexanoic acid, isononanoic acid, isooctanoic acid, 2-ethylheptanoic acid, heptanoic acid, capric acid and caprylic acid.
3. A composition according to claim 1, wherein n is an integer from 10 to 16.
4. A composition according to claim 1, wherein the quaternary phosphonium compound has the formula [(C41H 9 3 P CnH2n+l+C e 00* A composition according to claim 4, wherein the phosphonium compound is tributylphosphoniumtetradecyl chloride.
6. A composition according to claim 1, wherein the alkali metal salt of a alphatic C6-C12 monocarboxylic acid is the sodium salt of 2-ethylhexanoic acid. eno 0
7. A composition according to claim 1 for temporarily protecting freshly sawn timber.
8. A composition according to claim 1, which comprises conventional formulation auxiliaries. 9
9. A composition according to claim 8, which comprises water, alcohol and/or bases. A composition according to claim 9, wherein the base is sodium hydroxide.
11. A composition according to claim 1, wherein the weight ratio of phosphonium compound:free carboxylic acid is 1:1 to 1:50, preferably 1:4 to 1:10.
12. A method of protecting timber against growth by blue-stain and mold fungi comprising administering to such timber a quaternary phosphonium compound of formula [C 4 H 9 3 P CnH2n+l+]X or [(C 4 H 9 3 P CnH2n+112+SO 4 2 wherein n and X- are as defined in claim 1, in combination with an alkali metal salt of an aliphatic C 6 -C12 monocarboxylic acid. S13. Use according to claim 12 of an aqueous solution of the combination of the quaternary phosphonium compound and the alkali metal salt of an aliphatic C-C12 monocarboxylic acid.
14. A process for protecting timber against growth by blue-stain and mold fungi, which comprises treating said timber with a solution or dispersion which comprises a quaternary phosphonium compound of formula [(C 4 H 9 3 P CnH2n+I)+X or [(C 4 H9) 3 P CnH 2 n+12+SO4- wherein n and X~ are as defined in claim 1, and an alkali metal salt of an aliphatic C6-C12 monocarboxylic acid. a o A process according to claim 14, wherein an aqueous solution is used. DATED this 9th day of July, 1993 FMC CORPORATION (UK) LIMITED WATERMARK PATENT TRADEMARK ATTORNEYS THE ATRIUM 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRAl-IA 9 a 9 S. V r It The invention relates to a composition for protecting timber, especially freshly sawn timber, against growth by blue-stain and mold fungi. The novel composition is a formulation comprising at least one quaternary phosphonium compound of formula [(C4H9)3P CnH2n+l]+ X- or [(C4H9)3P CnH2n+112+SO4 2 wherein n is an integer from 8 to 16 and X- is an anion selected from the group consisting of CI-, Br, N03- and HSO4-, and at least one alkali metal salt of an aliphatic C6-C12 monocarboxylic acid. i a cc o oo oo 100892cmd/mk
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH347391 | 1991-11-27 | ||
| CH3473/91 | 1991-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2973292A AU2973292A (en) | 1993-06-03 |
| AU641599B2 true AU641599B2 (en) | 1993-09-23 |
Family
ID=4256728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU29732/92A Ceased AU641599B2 (en) | 1991-11-27 | 1992-11-26 | Composition for protecting timber from fungal growth |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU641599B2 (en) |
| BR (1) | BR9204576A (en) |
| CA (1) | CA2084029A1 (en) |
| ZA (1) | ZA928476B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0109354A1 (en) * | 1982-10-06 | 1984-05-23 | Ciba-Geigy Ag | Biocidally active mixture |
| AU549306B2 (en) * | 1981-02-05 | 1986-01-23 | Domtar Inc. | Quanternary ammonium composition |
| AU610117B2 (en) * | 1987-01-30 | 1991-05-16 | Albright & Wilson Uk Limited | Wood treatment composition and process |
-
1992
- 1992-11-03 ZA ZA928476A patent/ZA928476B/en unknown
- 1992-11-26 AU AU29732/92A patent/AU641599B2/en not_active Ceased
- 1992-11-26 BR BR9204576A patent/BR9204576A/en not_active Application Discontinuation
- 1992-11-27 CA CA002084029A patent/CA2084029A1/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU549306B2 (en) * | 1981-02-05 | 1986-01-23 | Domtar Inc. | Quanternary ammonium composition |
| EP0109354A1 (en) * | 1982-10-06 | 1984-05-23 | Ciba-Geigy Ag | Biocidally active mixture |
| AU610117B2 (en) * | 1987-01-30 | 1991-05-16 | Albright & Wilson Uk Limited | Wood treatment composition and process |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA928476B (en) | 1993-05-06 |
| AU2973292A (en) | 1993-06-03 |
| BR9204576A (en) | 1993-06-01 |
| CA2084029A1 (en) | 1993-05-28 |
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