CA2088714C - Synergistic combinations of cyproconazole - Google Patents
Synergistic combinations of cyproconazole Download PDFInfo
- Publication number
- CA2088714C CA2088714C CA002088714A CA2088714A CA2088714C CA 2088714 C CA2088714 C CA 2088714C CA 002088714 A CA002088714 A CA 002088714A CA 2088714 A CA2088714 A CA 2088714A CA 2088714 C CA2088714 C CA 2088714C
- Authority
- CA
- Canada
- Prior art keywords
- fungicidal composition
- wood
- weight
- formula
- cyproconazole
- 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 - Lifetime
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- 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
- B27K3/343—Heterocyclic compounds
-
- 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
- B27K3/40—Aromatic compounds halogenated
-
- 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
- B27K3/50—Mixtures of different organic impregnating agents
-
- 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
- B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Bending Of Plates, Rods, And Pipes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to novel fungicidal compositions based on cyproconazole and quaternary ammonium salts which have surprisingly powerful synergistic effects in the control and prevention of wood-destroying fungi.
Description
HOECHST HOLLAND N.V. HOE 92/F 027 Dr.AB/Ht Synergistic combinations of cyproconazole The cyproconazole-type fungicides found in recent years have good fungicidal activity (cf. US Patent 4,549,439) and have an activity against human and animal dermatophy tes and against phytopathogenic fungi.
Novel fungicidal agents based on cyproconazole and quaternary ammonium salts which have surprisingly power-ful synergistic activities in 'the control and prevention of wood-destroying fungi have now been found.
The use of mixtures which entail synergistic .effects has considerable economic but also ecological advantages.
Synergism is to be understood as meaning the mutually enhancing activity of two or more substances. In the present case, the combined application of two fungicides allows the application rate of the fungic:Ldes to be reduced while still maintaining an equally good fun gicidal activity, or that identical application rates of the fungicides result in a greater activity than the activity to be expected from the individual7Ly employed active substances.
The utilization of such synergistic effects allow the application rates of the components to be considerably reduced, and it is possible to control a broad range of wood-destroying fungi. The reduced application rates relate to the quaternary ammonium salts, but also to cyproconazole.
In the present case, cyproconazole is combined with compounds which considerably enhance the activity of the fungicide, which allows the identical activity to be obtained by using a lower concentration of the fungicide.
In addition, the combinations according to the invention are active even when used at low application rates. They are therefore outstandingly suitable for controlling wood fungi in wood and masonxy.
The present invention therefore relates to fungicidal compositions which comprise A) cyproconazole (Formula T) N
N
~N~ 0 H
I
CN2-C / ~ CI
(I) H
in combination with B) inorganic or organic ammanium salts of the formula II
(II) R 2_~ +-R 4 R
n in which Rl-R~ are identical or different and are an organic substituent which has up to 18 carbon atoms and which is bonded by a carbon-nitrogen bond, or three of the radicals R1-R'' together with the nitro-gen atom farm a heteroaromatic system, for example pyridinium, Xn- is the anion of an inorganic or organic n-basic acid, and n is 1, 2 or 3.
~~c~'3~~~'i~
Novel fungicidal agents based on cyproconazole and quaternary ammonium salts which have surprisingly power-ful synergistic activities in 'the control and prevention of wood-destroying fungi have now been found.
The use of mixtures which entail synergistic .effects has considerable economic but also ecological advantages.
Synergism is to be understood as meaning the mutually enhancing activity of two or more substances. In the present case, the combined application of two fungicides allows the application rate of the fungic:Ldes to be reduced while still maintaining an equally good fun gicidal activity, or that identical application rates of the fungicides result in a greater activity than the activity to be expected from the individual7Ly employed active substances.
The utilization of such synergistic effects allow the application rates of the components to be considerably reduced, and it is possible to control a broad range of wood-destroying fungi. The reduced application rates relate to the quaternary ammonium salts, but also to cyproconazole.
In the present case, cyproconazole is combined with compounds which considerably enhance the activity of the fungicide, which allows the identical activity to be obtained by using a lower concentration of the fungicide.
In addition, the combinations according to the invention are active even when used at low application rates. They are therefore outstandingly suitable for controlling wood fungi in wood and masonxy.
The present invention therefore relates to fungicidal compositions which comprise A) cyproconazole (Formula T) N
N
~N~ 0 H
I
CN2-C / ~ CI
(I) H
in combination with B) inorganic or organic ammanium salts of the formula II
(II) R 2_~ +-R 4 R
n in which Rl-R~ are identical or different and are an organic substituent which has up to 18 carbon atoms and which is bonded by a carbon-nitrogen bond, or three of the radicals R1-R'' together with the nitro-gen atom farm a heteroaromatic system, for example pyridinium, Xn- is the anion of an inorganic or organic n-basic acid, and n is 1, 2 or 3.
~~c~'3~~~'i~
The compounds of type B are preferably ammonium salts in which R1-R'' are identical or different and are (C1-C1g)-alkyl , ( C~-C13 ) -aralkyl, such as benzyl, ( C1-C6 ) -alkyoxy-( C1-Clz ) 'alkyl , [ -CHz-CHz-0 ] R-H or [ -CH ( CH3 ) -CHz-0 ] R H and x is 1, 2 or 3. Particularly preferred salts are those in which R1 and Rz are in each case ( C1-C,, ) -alkyl, in par ticular methyl, R3 and R4 are in each case (Ca-Clz)-alkyl, in particular decyl. Preferred anions xn- are C1-, Br-, 5042 , HSO,, , PO,,3 , HP0,,2 , HZPO4 , CH3C00 , C00zz , SCN , In particular Cl-.
Most of the wood-destroying fungi are Basidiomycetes, but Ascomycetes and Deuteromycetes can also be found. The compositions according to the invention are preferably used against Basidiomycetes, for example against Coniophora, Gloephyllum, Poria, Serpula and Coriolus. The following fields of application are of particular interest: preventive and curative treatment of wood, and curative treatment of wood and masonry.
The compounds of type B can be combined with cyprocon-azole to give a range of combinations. Cyproconazole and quaternary ammonium salts are commercially available.
The mixing ratios of the individual components in the combinations according to the invention can vary within wide limits. However, quantitative ratios of between 2:5 and I:25, preferably between 1:4 and 1:6, are selected for practical reasons.
The mixtures according to the invention can be in the form of water-dilutable concentrations which are then applied in a customary manner in the form of a dilution with water, or in the form of so-called tank mixes which are prepared by concomitant dilution of the separately formulated components with water immediately prior to application. They can also be applied in the form of aqueous ready-for-use solutions.
_ ~~~~Ml~~
The application rates of the fungicides of type A in the active substance mixtures are generally between 1 g/1 and 100 g/1, the application rates of B are between 5 g/1 and 500 g/1; the total amount of product combination to be applied is 15 1/m3 to 600 1/m3 of wood.
The compositions according to the invention can be marketed in the form of the .conventional preparations which are known to a person skilled in the art. They are preferably marketed in the form of water-dilutable concentrates or ready-for-use solutions. The formulated compositions contain for example 0.1 to 50~ by weight of the active substance combinations according to the invention.
Examples of inert substances which can be used are n-butyl glycolate, polyglycol ether or dipropylene glycol monoethyl ether.
In the case of fungicidal compositions, the concentra-tions of the active substances in the commercially available formulations can vary. The active substance concentration in emulsifiable concentrates is approx. 1 to 50~.
If appropriate, the commercial concentrates are diluted in the customary manner for application. The application rate and the concentration required varies depending on the field of application, for example for the treatment of wood without or with contact with the soil or water.
A combination of the active substances means that the fungicidal active substances are applied jointly or a few days one after the other, in the form of a so-called split application.
If required, the compositions according to the invention can be combined with other active substances, preferably 2~~~'~~~
_ 5 _ with fungicides and insecticides. 'Unless otherwise indicated, percentages are percent by weight. The invention is illustrated by the example which follows without limiting it thereto:
Example Determination of the activity of the cyproconazole in combination with dimethyldidecylammonium chloride against wood-destroying Basidiomycetes.
The active substances were tasted in accordance with European Testing Standards ES 89 (1979) rind 113 (1986).
Treatment with the active substances prevents the wood from being destroyed. The effect of the treatment is quantified indirectly via the non-existing weight loss of the wood samples.
The wood sample used was pine sapwood, and the test fungi used were Coniophora puteana (cellar fungus), Poria plazenta, Cloeophyllum trabeum and Trametes (Coriolus) versicolor. Markedly smaller amounts of the combination according to the invention of cyproconazole (A: 2-(4-chlorophenyl)-3-cyclopropyl-3-methyl-1-(1H,1,2,4-triazol-1-yl)-butan-2-ol) and dimethyldidecylammanium chloride (B1) have the same result (0$ weight loss) as cyproconazole or B1 alone. Comparably good results were also obtained when beech was used as the wood sample.
~i~i Table: Pine sapwood Amount (g/m3) of active Weight Loss Substance at 0~
Fungi A+H1 A B1 Coniophora 121 g + 247 g 12,415 g 605 g Gloephyllum 119.5 g 247 g 12,505 g +
+ 597.5 g Poria 121 g + 243 g 3,175 g 605 g Coriolus 105 g + 418 g 2,675 g 525 g
Most of the wood-destroying fungi are Basidiomycetes, but Ascomycetes and Deuteromycetes can also be found. The compositions according to the invention are preferably used against Basidiomycetes, for example against Coniophora, Gloephyllum, Poria, Serpula and Coriolus. The following fields of application are of particular interest: preventive and curative treatment of wood, and curative treatment of wood and masonry.
The compounds of type B can be combined with cyprocon-azole to give a range of combinations. Cyproconazole and quaternary ammonium salts are commercially available.
The mixing ratios of the individual components in the combinations according to the invention can vary within wide limits. However, quantitative ratios of between 2:5 and I:25, preferably between 1:4 and 1:6, are selected for practical reasons.
The mixtures according to the invention can be in the form of water-dilutable concentrations which are then applied in a customary manner in the form of a dilution with water, or in the form of so-called tank mixes which are prepared by concomitant dilution of the separately formulated components with water immediately prior to application. They can also be applied in the form of aqueous ready-for-use solutions.
_ ~~~~Ml~~
The application rates of the fungicides of type A in the active substance mixtures are generally between 1 g/1 and 100 g/1, the application rates of B are between 5 g/1 and 500 g/1; the total amount of product combination to be applied is 15 1/m3 to 600 1/m3 of wood.
The compositions according to the invention can be marketed in the form of the .conventional preparations which are known to a person skilled in the art. They are preferably marketed in the form of water-dilutable concentrates or ready-for-use solutions. The formulated compositions contain for example 0.1 to 50~ by weight of the active substance combinations according to the invention.
Examples of inert substances which can be used are n-butyl glycolate, polyglycol ether or dipropylene glycol monoethyl ether.
In the case of fungicidal compositions, the concentra-tions of the active substances in the commercially available formulations can vary. The active substance concentration in emulsifiable concentrates is approx. 1 to 50~.
If appropriate, the commercial concentrates are diluted in the customary manner for application. The application rate and the concentration required varies depending on the field of application, for example for the treatment of wood without or with contact with the soil or water.
A combination of the active substances means that the fungicidal active substances are applied jointly or a few days one after the other, in the form of a so-called split application.
If required, the compositions according to the invention can be combined with other active substances, preferably 2~~~'~~~
_ 5 _ with fungicides and insecticides. 'Unless otherwise indicated, percentages are percent by weight. The invention is illustrated by the example which follows without limiting it thereto:
Example Determination of the activity of the cyproconazole in combination with dimethyldidecylammonium chloride against wood-destroying Basidiomycetes.
The active substances were tasted in accordance with European Testing Standards ES 89 (1979) rind 113 (1986).
Treatment with the active substances prevents the wood from being destroyed. The effect of the treatment is quantified indirectly via the non-existing weight loss of the wood samples.
The wood sample used was pine sapwood, and the test fungi used were Coniophora puteana (cellar fungus), Poria plazenta, Cloeophyllum trabeum and Trametes (Coriolus) versicolor. Markedly smaller amounts of the combination according to the invention of cyproconazole (A: 2-(4-chlorophenyl)-3-cyclopropyl-3-methyl-1-(1H,1,2,4-triazol-1-yl)-butan-2-ol) and dimethyldidecylammanium chloride (B1) have the same result (0$ weight loss) as cyproconazole or B1 alone. Comparably good results were also obtained when beech was used as the wood sample.
~i~i Table: Pine sapwood Amount (g/m3) of active Weight Loss Substance at 0~
Fungi A+H1 A B1 Coniophora 121 g + 247 g 12,415 g 605 g Gloephyllum 119.5 g 247 g 12,505 g +
+ 597.5 g Poria 121 g + 243 g 3,175 g 605 g Coriolus 105 g + 418 g 2,675 g 525 g
Claims (10)
1. A fungicidal composition which comprises A) cyproconazole of the Formula I
in combination with B) inorganic or organic ammonium salts of the formula II
in which R1-R1 are identical or different and are an organic substituent which has up to 18 carbon atoms and which is bonded by a carbon-nitrogen bond, or three of the radicals R1-R4 together with the nitro-gen atom form a heteroaromatic system, X n- is the anion of an inorganic or organic n-basic acid, and n is 1, 2 or 3.
in combination with B) inorganic or organic ammonium salts of the formula II
in which R1-R1 are identical or different and are an organic substituent which has up to 18 carbon atoms and which is bonded by a carbon-nitrogen bond, or three of the radicals R1-R4 together with the nitro-gen atom form a heteroaromatic system, X n- is the anion of an inorganic or organic n-basic acid, and n is 1, 2 or 3.
2. The fungicidal composition as claimed in claim 1, wherein R1 and R2 are identical or different and are each (C1-C4) alkyl, and R3 and R4 are identical or different and are each (C8-C12) alkyl.
3. The fungicidal composition as claimed in claim 2, wherein R1 and R2 are each methyl, and R3 and R4 are each decyl.
4. A fungicidal composition as claimed in claim 1, 2 or 3, which comprises the active substances A and B in a ratio by weight of 1:2.5 to 1:25.
5. The fungicidal composition as claimed in claim 4, wherein the ratio by weight of A:B is 1:4 to 1:6.
6. The fungicidal composition as claimed in any one of claims 1 to 5, which comprises 0,1 to 50% by weight of active substance mixture and 99.5 - 50% by weight of conventional formulation auxiliaries for preparations as sprayable solutions.
7. A method of controlling harmful fungal growth on wood, which comprises applying an effective fungicidal amount of the fungicidal composition according to any one of claims 1 to 6.
8. The method as claimed in claim 7, which comprises applying the fungicidal composition in amounts from 15 to 600 l/m3 of wood.
9. The method as claimed in claim 7 or 8, which comprises using spray mixtures which comprise 1 to 100 g/l of the compound of the formula I and 5 to 500 g/l of a compound of the formula II.
10. Use of the fungicidal composition as claimed in any one of claims 1 to 6, for controlling wood-destroying fungi, which comprises applying the active substances concomitantly or shortly one after the other.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4203090A DE4203090A1 (en) | 1992-02-04 | 1992-02-04 | SYNERGISTIC COMBINATIONS OF CYPROCONAZOLE |
| DEP4203090.0 | 1992-02-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2088714A1 CA2088714A1 (en) | 1993-08-05 |
| CA2088714C true CA2088714C (en) | 2003-10-21 |
Family
ID=6450902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002088714A Expired - Lifetime CA2088714C (en) | 1992-02-04 | 1993-02-03 | Synergistic combinations of cyproconazole |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0554833B1 (en) |
| JP (1) | JP3693355B2 (en) |
| AT (1) | ATE186625T1 (en) |
| AU (1) | AU656836B2 (en) |
| CA (1) | CA2088714C (en) |
| DE (2) | DE4203090A1 (en) |
| DK (1) | DK0554833T3 (en) |
| FI (1) | FI107013B (en) |
| MY (1) | MY116458A (en) |
| NO (2) | NO303043B1 (en) |
| NZ (1) | NZ245824A (en) |
| ZA (1) | ZA93732B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9202378D0 (en) | 1992-02-05 | 1992-03-18 | Sandoz Ltd | Inventions relating to fungicidal compositions |
| DE4233337A1 (en) | 1992-10-05 | 1994-04-07 | Bayer Ag | Microbicidal agents |
| AU732685B2 (en) * | 1995-12-20 | 2001-04-26 | Nigel Paul Maynard | Solubilizing biocides using anhydrous "onium" compounds as solvent |
| DK1713331T3 (en) * | 2004-02-04 | 2008-02-04 | Janssen Pharmaceutica Nv | Synergistic antifungal DDAC compositions |
| GB2438404A (en) * | 2006-05-24 | 2007-11-28 | Arch Timber Protection Ltd | Preserving wood with an amine oxide, an azole and a specified amine or quaternary ammonium compound, in synergistic proportions |
| JP2012219069A (en) * | 2011-04-11 | 2012-11-12 | Neos Co Ltd | Method for controlling mold, and liquid mold-controlling agent composition |
| GB201119139D0 (en) | 2011-11-04 | 2011-12-21 | Arch Timber Protection Ltd | Additives for use in wood preservation |
| CN110587753A (en) | 2014-05-02 | 2019-12-20 | 奥麟木材保护有限公司 | Wood preservative composition |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3605551A1 (en) * | 1986-02-21 | 1987-09-10 | Bayer Ag | FUNGICIDAL AGENT |
| BE904660A (en) * | 1986-04-23 | 1986-08-18 | Janssen Pharmaceutica Nv | Synergistic wood preservatives - comprising ammonium salt and imidazole or triazole deriv. |
| GB8617780D0 (en) * | 1986-07-21 | 1986-08-28 | Sandoz Ltd | Fungicides |
| DE3800094C2 (en) * | 1987-01-14 | 1998-05-14 | Ciba Geigy Ag | Process and hydrophobic preparation for combating cut parasites in plants |
| FR2609366A1 (en) * | 1987-01-14 | 1988-07-15 | Sandoz Sa Produits | Process for controlling diseases of pruning wounds of perennial plants |
| FR2626740B1 (en) * | 1988-02-08 | 1990-10-19 | Xylochimie | EMULSIONABLE CONCENTRATES OF BIOCIDAL MATERIALS, THE AQUEOUS MICROEMULSIONS OBTAINED AND THE APPLICATION OF THESE MICROEMULSIONS TO THE TREATMENT OF WOOD |
| DE3811302A1 (en) * | 1988-04-02 | 1989-10-19 | Bayer Ag | DERIVATIVES OF TRIAZOLYLMETHYL-CYCLOPROPYL CARBINOL AS A MATERIAL PROTECTIVE |
| ATE177902T1 (en) * | 1990-11-02 | 1999-04-15 | Novartis Erfind Verwalt Gmbh | FUNGICIDES |
-
1992
- 1992-02-04 DE DE4203090A patent/DE4203090A1/en not_active Withdrawn
-
1993
- 1993-02-02 EP EP93101576A patent/EP0554833B1/en not_active Expired - Lifetime
- 1993-02-02 DE DE59309869T patent/DE59309869D1/en not_active Expired - Lifetime
- 1993-02-02 AT AT93101576T patent/ATE186625T1/en active
- 1993-02-02 FI FI930452A patent/FI107013B/en not_active IP Right Cessation
- 1993-02-02 DK DK93101576T patent/DK0554833T3/en active
- 1993-02-02 NZ NZ245824A patent/NZ245824A/en not_active IP Right Cessation
- 1993-02-03 MY MYPI93000174A patent/MY116458A/en unknown
- 1993-02-03 ZA ZA93732A patent/ZA93732B/en unknown
- 1993-02-03 CA CA002088714A patent/CA2088714C/en not_active Expired - Lifetime
- 1993-02-03 AU AU32821/93A patent/AU656836B2/en not_active Expired
- 1993-02-03 NO NO930379A patent/NO303043B1/en not_active IP Right Cessation
- 1993-02-04 JP JP01765593A patent/JP3693355B2/en not_active Expired - Lifetime
-
1998
- 1998-01-23 NO NO19980307A patent/NO321134B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO980307L (en) | 1993-08-05 |
| EP0554833A1 (en) | 1993-08-11 |
| ATE186625T1 (en) | 1999-12-15 |
| FI107013B (en) | 2001-05-31 |
| DE59309869D1 (en) | 1999-12-23 |
| DK0554833T3 (en) | 2000-05-08 |
| EP0554833B1 (en) | 1999-11-17 |
| MY116458A (en) | 2004-02-28 |
| ZA93732B (en) | 1993-10-11 |
| NO321134B1 (en) | 2006-03-20 |
| NO930379L (en) | 1993-08-05 |
| JPH06256115A (en) | 1994-09-13 |
| AU3282193A (en) | 1993-08-05 |
| NO303043B1 (en) | 1998-05-25 |
| JP3693355B2 (en) | 2005-09-07 |
| FI930452A0 (en) | 1993-02-02 |
| NO980307D0 (en) | 1998-01-23 |
| DE4203090A1 (en) | 1993-08-19 |
| FI930452A (en) | 1993-08-05 |
| NZ245824A (en) | 1995-01-27 |
| AU656836B2 (en) | 1995-02-16 |
| NO930379D0 (en) | 1993-02-03 |
| CA2088714A1 (en) | 1993-08-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0641164B1 (en) | Preservatives for wood and other cellulosic materials | |
| AU623514B2 (en) | Synergistic compositions containing propiconazole and tebuconazole | |
| US8173681B2 (en) | Method for the protection of materials | |
| KR101298774B1 (en) | Fungicidal mixtures for wood preservation | |
| US6726937B2 (en) | Antifungal composition | |
| CA2088714C (en) | Synergistic combinations of cyproconazole | |
| USRE36798E (en) | Preservatives for wood and other cellulosic materials | |
| US6423732B1 (en) | Synergistic combinations of cyproconazole | |
| EP0269817B1 (en) | Agent or concentrate for the preservation of wood and wooden materials | |
| US6824830B1 (en) | Wood treatment | |
| EP0454431B1 (en) | Wood preservative composition | |
| EP1135239B1 (en) | Wood preservative formulations | |
| US6399623B1 (en) | Wood treatment | |
| JP2017165691A (en) | Antimicrobial composition for wood | |
| AU659203C (en) | Preservatives for wood and other cellulosic materials | |
| GB2336539A (en) | Wood treatment using fluquinconazole | |
| JP2017165692A (en) | Antimicrobial composition for wood | |
| EP1937449A1 (en) | Use of diclosan for wood protection |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20130204 |