CA1075099A - Process and composition for the treatment of wood - Google Patents
Process and composition for the treatment of woodInfo
- Publication number
- CA1075099A CA1075099A CA250,447A CA250447A CA1075099A CA 1075099 A CA1075099 A CA 1075099A CA 250447 A CA250447 A CA 250447A CA 1075099 A CA1075099 A CA 1075099A
- Authority
- CA
- Canada
- Prior art keywords
- wood
- composition
- weight
- active ingredient
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/38—Aromatic compounds
- B27K3/42—Aromatic compounds nitrated, or nitrated and halogenated
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
The invention is concerned with a process and a com-position for the treatment of wood in order to obtain a protect-ion of the wood against wood-destroying fungi. The essential active ingredient used in the process and composition is the chemical compound N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfone-anilide, which is a compound known per se.
The invention is concerned with a process and a com-position for the treatment of wood in order to obtain a protect-ion of the wood against wood-destroying fungi. The essential active ingredient used in the process and composition is the chemical compound N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfone-anilide, which is a compound known per se.
Description
`, This invention is for improvements in or relating to wood protection, more particularly for the new use of the com-pound of formula 3 ~ -Ccl2-ccl2F
[N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfoneanilide]
as a wood protectant.
The preparation of the compound I is described in British Patent Specification No. 1242266 in which the compound J and a use thereof is claimed. From this specification it is known that the compound I shows activity against Eimeria tenella.
It is also known that the compound I besides acaricidal activity shows activity against various fungi such as for example l`-i Rhizoctonia solani and Fusarium solani (known to be active, i.e.
~,. .
as plantpathogenes),as well as Aspergillus niger and Penicillium sp. These later organisms are known, i.a. to cause discolora-tions of wood surfaces and of paints.
It is well-known that in view of the great differences met within the fungi, good activity against one class of fungi does not necessarily mean good activity against other classes, even any activity at all.
Much to our surprise we have now found that the com-pound I shows very high activity against wood destroying fungi such a~ for example Coniophora cerebella, Polyporus vaporarius and Merulius lacrymans. This activity is very high not only when compared with the activity of other well-known plant patho-genic fungicides, but also when compared with some well-known and widespread wood protectants such as TBTO (tributyltinoxide), PCP (pentachlorophenol) and dichlofluanid.
~B - 2 - ~
`
Accordingly, the invention related to a process of treating wood by means of compound I, in order to prevent or at least hamper an attack by wood-destroying fungi.
`~ Suitable compositions of the present invention are pre-pared by incorporating the compound I in any of the liquids nor-mally used in preparing wood protective compositions, and first and foremost such organic liquids in which the compound I i8 soluble to the desired concentration. Usually a liquid hydro-; carbon, or mixture of hydrocarbons, is used, preferably a liquid aliphatic hydrocarbon or a mixture of such aliphatic hydrocarbon or a mixture of such aliphatic hydrocarbon or hydrocarbons with q a proportion of aromatic hydrocarbons or related compounds, and - -- preferably white spirit or kerosene or similar commercial liquid hydrocarbon fractions. The concentration of active substance in the liquid composition usually will range from 0,196 and 10% --by weight, and preferably from 0,1% to 296 by weight. However, the concentration is not critical, and should only be high enough to secure that a protection is obtained by means of the selected type of treatment. The types of treatment made use of are the conventional ones, which are abundantly described in the tech-nical literature. For example, detailed descriptions may be found in F.P. Kollmann, Wilfred A. Coté Jr., "Principles of Wood ~ Science and Technology", Vol. 1, chapter 5, p. 136-157, Springer-- Verlag, New York (1968), F. P. Kollmann, Wilfred A. Côté Jr., Alfred J. Stamm, "Principles of Wood Science and Technology", Vol. 2, chapter 2, p. 107-111, Springer-Verlag, New York (1975), and "Ullmann's Enzyklopadie der Technischen Chemie", 3rd Edition (1957), Vol. 8 p. 539 ff. When using such treatment, comprising various surface treatments (brushing, immersion etc.), sap-displacement methods ~..~
' ' , ..
(such as the Boucherie-method), tank-impregnation methods (such as Ruping's method or Rutger's method), a concentration of active substance in the above-mentioned range of 0,1 to 10% by weight will always be useful, and a concentration of from 0,1 to 2~ will normally be satisfactory. Naturally, it can be desired to some-what vary the composition, and especially the concentration, according to various factors such as the type of wood, and the use made of the wood, the degree of wanted protection, and the method of treatment (for example, brushing or impregnation by means of pressure), but the skilled art worker will without any difficulties know which composition, and method, will be pre-ferable.
The composition may, if so desired, contain an ingre-dient serving to help in binding the active substance to the wood. An addition of such binder is per se well-known in the art. Use may be made, for example, of a usual alkyd-resin binder or of linseed oil or other commonly used varnish material. The concentration of such binder may vary considerably, in accord-ance with specific desires, for example, up to 10% by weight or even more. As a suitable composition for treating wood may be mentioned a liquid composition containing about 4~ by weight of the compound I, 9% by weight of a usual alkyd-resin binder (or a similar quantity of linseed oil) and 87% by weight of white spirit.
The invention is useful for the protection of all kinds of wood susceptible to the attack of wood-destroying fungi, such as pine, fir, beech, for example, in the form of posts, poles, boards, beams and all kinds of timber for building purposes.
The activity of the substance in question is exemplified by test for activity against the wood destroying fungus Coniophora - ~ - 4 -`` 1075099 cerebella.
Two different test methods were used.
'`
Test method 1 Slices of pine wood, 7 x i.6 x 0.2 cm3 were dried 24 , hours at 103C, and then weighed.
; A concentration series of 4, 2, 1, 0.5, 0.25 and 0.125%
of the substance for testing was prepared as a solution in white -1 spirit containing 9% of an alkyd binder.
Impregnation was made by dipping the wood slices for a short time into the solution. The wet slices were weïghed, and uptake should be about 100 kg. of the solution per cubic meter.
j After drying two days at room temperature the slices , were packed in steramide bags and sterilized by radiation, pre-. ferably U.V. or gamma-radiation.
Glass bottles containing 500 ml of soil specially nutrified for the growing of Coniophora cerebella ~a~ ste~ilized by autoclaving for 3 hours at 120C, and then cooled.
~ he wood slices were placed in the bottles, the soil ino-culated with Coniophora cerebella,and incubated four weeks at 22Cand 70% relative humidity.
After incubation the slices were carefully brushed, then dried at 103C and weighed. The weight loss was calculated in per cent-of the initial weight.
~ Test method 2.
`/ Test specimens of beech and pine are thoroughly impregnated with 0.25% solutions of the compounds to be tested.
The specimens are then placed in unsterilized standard soil and deposited at 22C and 90% relative humidity.
~ 30 After 12 weeks the specimens are removed from the soil, ,~, . .
~: .
cleaned and dried. The weight-loss is determined in per cent of the initial weight.
Example No. 1.
Activity of compound I compared with well-known wood protectants.
Using test method 1. the following compounds were tested, A Compound I
B PCP ~ abiethylamine (1/1 by moles) C PCP + TBTO (1/1 by moles) D Dichlofluanid - E 2,3-dichloro-1,4-naphthoquinone Table No. 1.
- Comp. per cent active ingredient 4% 2% 1% 0.5% 0.25%0.125% 0% 0%
A 0.0 0.00.0 0.0 0.0 4 18.9 33.0 B 1.8 6.218.4 29.0 - - 19.8 40.4 C 0.0 0.00.0 3.6 18.0 >20 20.7 31.9 D ~ 0;7 0.90.7 1.2 14.0 >20 18.5 38.3 E _ 19.026.6 27.0 - - 18.8 37.9 The results listed are % weight-loss.
Example No. 2.
Activity of compound I compared with well-known plant -patogenic fungicides.
Using test method 1. the following compounds were tested, o N-S-~-Cl Folpet.
Cl .
B:~ Cl N-S-~-Cl Captan .
C:3 N-~-N-S-C-F Dichlofluanid CH3~ 1 ¦
Cl , - ~ .
. , .
10, ~ D:~ N-S-~-CH Difolatan ,i.~ ' E: ~ ONH-Bu Benomyl ~: - ~N H-C00-CH3 .'~ ' .
~ .
-~
~20 F: ~ ~ H-- CH ~hiabendazole ;,' '` ~ .
G: Compound I.
., .
. .
.
.j . . .
.
~ . . . . ..
Table No. 2 Comp. Per cent active ingredient _ 4% 2% 1% 0.5%0.25% 0.125%
A 6 11 13 18 >20 ?20 ; . B 4 18 >20 >20 >20 ~20 C 1 1 1 1 14 ~20 D 9 10 ~ 13 18 >20 ~20 E - 6 16 ~20 ~20 >20 F - 12 ~20 >20- ~20 >20 -The results listed are % weight-loss - Example No. 3.
By use of test method 2 the compounds mentioned in example 1 were tested.
. The only specimens without microbial attack and weight-loss were those impregnated with compound I. All other specimens showed weight-loss in the range from 12 to more than 20%.
, . ' .
. j '~ .. ' . ' ` ~ `', ' -
[N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanesulfoneanilide]
as a wood protectant.
The preparation of the compound I is described in British Patent Specification No. 1242266 in which the compound J and a use thereof is claimed. From this specification it is known that the compound I shows activity against Eimeria tenella.
It is also known that the compound I besides acaricidal activity shows activity against various fungi such as for example l`-i Rhizoctonia solani and Fusarium solani (known to be active, i.e.
~,. .
as plantpathogenes),as well as Aspergillus niger and Penicillium sp. These later organisms are known, i.a. to cause discolora-tions of wood surfaces and of paints.
It is well-known that in view of the great differences met within the fungi, good activity against one class of fungi does not necessarily mean good activity against other classes, even any activity at all.
Much to our surprise we have now found that the com-pound I shows very high activity against wood destroying fungi such a~ for example Coniophora cerebella, Polyporus vaporarius and Merulius lacrymans. This activity is very high not only when compared with the activity of other well-known plant patho-genic fungicides, but also when compared with some well-known and widespread wood protectants such as TBTO (tributyltinoxide), PCP (pentachlorophenol) and dichlofluanid.
~B - 2 - ~
`
Accordingly, the invention related to a process of treating wood by means of compound I, in order to prevent or at least hamper an attack by wood-destroying fungi.
`~ Suitable compositions of the present invention are pre-pared by incorporating the compound I in any of the liquids nor-mally used in preparing wood protective compositions, and first and foremost such organic liquids in which the compound I i8 soluble to the desired concentration. Usually a liquid hydro-; carbon, or mixture of hydrocarbons, is used, preferably a liquid aliphatic hydrocarbon or a mixture of such aliphatic hydrocarbon or a mixture of such aliphatic hydrocarbon or hydrocarbons with q a proportion of aromatic hydrocarbons or related compounds, and - -- preferably white spirit or kerosene or similar commercial liquid hydrocarbon fractions. The concentration of active substance in the liquid composition usually will range from 0,196 and 10% --by weight, and preferably from 0,1% to 296 by weight. However, the concentration is not critical, and should only be high enough to secure that a protection is obtained by means of the selected type of treatment. The types of treatment made use of are the conventional ones, which are abundantly described in the tech-nical literature. For example, detailed descriptions may be found in F.P. Kollmann, Wilfred A. Coté Jr., "Principles of Wood ~ Science and Technology", Vol. 1, chapter 5, p. 136-157, Springer-- Verlag, New York (1968), F. P. Kollmann, Wilfred A. Côté Jr., Alfred J. Stamm, "Principles of Wood Science and Technology", Vol. 2, chapter 2, p. 107-111, Springer-Verlag, New York (1975), and "Ullmann's Enzyklopadie der Technischen Chemie", 3rd Edition (1957), Vol. 8 p. 539 ff. When using such treatment, comprising various surface treatments (brushing, immersion etc.), sap-displacement methods ~..~
' ' , ..
(such as the Boucherie-method), tank-impregnation methods (such as Ruping's method or Rutger's method), a concentration of active substance in the above-mentioned range of 0,1 to 10% by weight will always be useful, and a concentration of from 0,1 to 2~ will normally be satisfactory. Naturally, it can be desired to some-what vary the composition, and especially the concentration, according to various factors such as the type of wood, and the use made of the wood, the degree of wanted protection, and the method of treatment (for example, brushing or impregnation by means of pressure), but the skilled art worker will without any difficulties know which composition, and method, will be pre-ferable.
The composition may, if so desired, contain an ingre-dient serving to help in binding the active substance to the wood. An addition of such binder is per se well-known in the art. Use may be made, for example, of a usual alkyd-resin binder or of linseed oil or other commonly used varnish material. The concentration of such binder may vary considerably, in accord-ance with specific desires, for example, up to 10% by weight or even more. As a suitable composition for treating wood may be mentioned a liquid composition containing about 4~ by weight of the compound I, 9% by weight of a usual alkyd-resin binder (or a similar quantity of linseed oil) and 87% by weight of white spirit.
The invention is useful for the protection of all kinds of wood susceptible to the attack of wood-destroying fungi, such as pine, fir, beech, for example, in the form of posts, poles, boards, beams and all kinds of timber for building purposes.
The activity of the substance in question is exemplified by test for activity against the wood destroying fungus Coniophora - ~ - 4 -`` 1075099 cerebella.
Two different test methods were used.
'`
Test method 1 Slices of pine wood, 7 x i.6 x 0.2 cm3 were dried 24 , hours at 103C, and then weighed.
; A concentration series of 4, 2, 1, 0.5, 0.25 and 0.125%
of the substance for testing was prepared as a solution in white -1 spirit containing 9% of an alkyd binder.
Impregnation was made by dipping the wood slices for a short time into the solution. The wet slices were weïghed, and uptake should be about 100 kg. of the solution per cubic meter.
j After drying two days at room temperature the slices , were packed in steramide bags and sterilized by radiation, pre-. ferably U.V. or gamma-radiation.
Glass bottles containing 500 ml of soil specially nutrified for the growing of Coniophora cerebella ~a~ ste~ilized by autoclaving for 3 hours at 120C, and then cooled.
~ he wood slices were placed in the bottles, the soil ino-culated with Coniophora cerebella,and incubated four weeks at 22Cand 70% relative humidity.
After incubation the slices were carefully brushed, then dried at 103C and weighed. The weight loss was calculated in per cent-of the initial weight.
~ Test method 2.
`/ Test specimens of beech and pine are thoroughly impregnated with 0.25% solutions of the compounds to be tested.
The specimens are then placed in unsterilized standard soil and deposited at 22C and 90% relative humidity.
~ 30 After 12 weeks the specimens are removed from the soil, ,~, . .
~: .
cleaned and dried. The weight-loss is determined in per cent of the initial weight.
Example No. 1.
Activity of compound I compared with well-known wood protectants.
Using test method 1. the following compounds were tested, A Compound I
B PCP ~ abiethylamine (1/1 by moles) C PCP + TBTO (1/1 by moles) D Dichlofluanid - E 2,3-dichloro-1,4-naphthoquinone Table No. 1.
- Comp. per cent active ingredient 4% 2% 1% 0.5% 0.25%0.125% 0% 0%
A 0.0 0.00.0 0.0 0.0 4 18.9 33.0 B 1.8 6.218.4 29.0 - - 19.8 40.4 C 0.0 0.00.0 3.6 18.0 >20 20.7 31.9 D ~ 0;7 0.90.7 1.2 14.0 >20 18.5 38.3 E _ 19.026.6 27.0 - - 18.8 37.9 The results listed are % weight-loss.
Example No. 2.
Activity of compound I compared with well-known plant -patogenic fungicides.
Using test method 1. the following compounds were tested, o N-S-~-Cl Folpet.
Cl .
B:~ Cl N-S-~-Cl Captan .
C:3 N-~-N-S-C-F Dichlofluanid CH3~ 1 ¦
Cl , - ~ .
. , .
10, ~ D:~ N-S-~-CH Difolatan ,i.~ ' E: ~ ONH-Bu Benomyl ~: - ~N H-C00-CH3 .'~ ' .
~ .
-~
~20 F: ~ ~ H-- CH ~hiabendazole ;,' '` ~ .
G: Compound I.
., .
. .
.
.j . . .
.
~ . . . . ..
Table No. 2 Comp. Per cent active ingredient _ 4% 2% 1% 0.5%0.25% 0.125%
A 6 11 13 18 >20 ?20 ; . B 4 18 >20 >20 >20 ~20 C 1 1 1 1 14 ~20 D 9 10 ~ 13 18 >20 ~20 E - 6 16 ~20 ~20 >20 F - 12 ~20 >20- ~20 >20 -The results listed are % weight-loss - Example No. 3.
By use of test method 2 the compounds mentioned in example 1 were tested.
. The only specimens without microbial attack and weight-loss were those impregnated with compound I. All other specimens showed weight-loss in the range from 12 to more than 20%.
, . ' .
. j '~ .. ' . ' ` ~ `', ' -
Claims (7)
1. A process for the treatment of wood in order to combat attack of wood-destroying fungi, characterized in that the wood is treated with a composition comprising the compound N-(1,1,2,2-tetrachloro-2-fluoroethylthio)-methanessulfone-anilide as the essential active ingredient.
2. A process as claimed in claim 1, characterized in that the wood is treated, at least on the surface or in a surface layer with a solution of the said active ingredient in a hydro-carbon-liquid.
3. A process as claimed in claim 2, characterized in that the solution contains the active ingredient in a concentra-tion in the range from 0.1% to 10% by weight.
4. A process as claimed in claim 3, characterized in that the solution contains the active ingredient in a concentra-tion in the range from 0.1% to 2% by weight.
5. A process as claimed in claim 2, characterized in that the composition also contains a binder for the active in-gredient.
6. A process as claimed in claim 5, characterized in that the binder is selected from the varnish materials consisting of alkyd-resin and linseed oil binders.
7. A process as claimed in claim 5, characterized in that the composition contains the binder in a concentration in the range from 2% to 10%.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17019/75A GB1528041A (en) | 1975-04-24 | 1975-04-24 | Process and composition for the treatment of wood |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1075099A true CA1075099A (en) | 1980-04-08 |
Family
ID=10087762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA250,447A Expired CA1075099A (en) | 1975-04-24 | 1976-04-20 | Process and composition for the treatment of wood |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS51130506A (en) |
| AU (1) | AU499840B2 (en) |
| BE (1) | BE840880A (en) |
| BR (1) | BR7602501A (en) |
| CA (1) | CA1075099A (en) |
| CH (1) | CH622207A5 (en) |
| DE (1) | DE2616682A1 (en) |
| DK (1) | DK136808B (en) |
| FR (1) | FR2308476A1 (en) |
| GB (1) | GB1528041A (en) |
| NL (1) | NL7604248A (en) |
| NO (1) | NO145605C (en) |
| NZ (1) | NZ180668A (en) |
| SE (1) | SE410158B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT296253B (en) * | 1967-10-05 | 1972-02-10 | Stauffer Chemical Co | Process for the preparation of new N-substituted 2-fluoro-1,1,2,2-tetrachloroethanesulfenic acid amides |
-
1975
- 1975-04-24 GB GB17019/75A patent/GB1528041A/en not_active Expired
-
1976
- 1976-03-29 DK DK137876AA patent/DK136808B/en unknown
- 1976-04-15 DE DE19762616682 patent/DE2616682A1/en not_active Withdrawn
- 1976-04-16 BE BE166263A patent/BE840880A/en unknown
- 1976-04-19 JP JP51043803A patent/JPS51130506A/en active Pending
- 1976-04-20 CA CA250,447A patent/CA1075099A/en not_active Expired
- 1976-04-22 NL NL7604248A patent/NL7604248A/en not_active Application Discontinuation
- 1976-04-22 AU AU13256/76A patent/AU499840B2/en not_active Expired
- 1976-04-23 NZ NZ180668A patent/NZ180668A/en unknown
- 1976-04-23 SE SE7604704A patent/SE410158B/en unknown
- 1976-04-23 NO NO761398A patent/NO145605C/en unknown
- 1976-04-23 FR FR7612036A patent/FR2308476A1/en active Granted
- 1976-04-23 CH CH514576A patent/CH622207A5/en not_active IP Right Cessation
- 1976-04-23 BR BR2501/76A patent/BR7602501A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU499840B2 (en) | 1979-05-03 |
| SE7604704L (en) | 1976-10-25 |
| DK136808B (en) | 1977-11-28 |
| NO761398L (en) | 1976-10-26 |
| NO145605C (en) | 1982-04-28 |
| DE2616682A1 (en) | 1976-11-11 |
| NZ180668A (en) | 1978-04-03 |
| FR2308476B1 (en) | 1978-05-19 |
| AU1325676A (en) | 1977-10-27 |
| BR7602501A (en) | 1976-10-19 |
| NL7604248A (en) | 1976-10-26 |
| BE840880A (en) | 1976-08-16 |
| NO145605B (en) | 1982-01-18 |
| SE410158B (en) | 1979-10-01 |
| DK137876A (en) | 1976-10-25 |
| FR2308476A1 (en) | 1976-11-19 |
| DK136808C (en) | 1978-05-08 |
| JPS51130506A (en) | 1976-11-12 |
| GB1528041A (en) | 1978-10-11 |
| CH622207A5 (en) | 1981-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |