HU215235B - Fatartósító oxatiazinok, készítmények és alkalmazásuk - Google Patents
Fatartósító oxatiazinok, készítmények és alkalmazásuk Download PDFInfo
- Publication number
- HU215235B HU215235B HU9600437A HU9600437A HU215235B HU 215235 B HU215235 B HU 215235B HU 9600437 A HU9600437 A HU 9600437A HU 9600437 A HU9600437 A HU 9600437A HU 215235 B HU215235 B HU 215235B
- Authority
- HU
- Hungary
- Prior art keywords
- hydrogen
- alkyl
- formula
- phenyl
- wood
- Prior art date
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- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical class O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000003171 wood protecting agent Substances 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 239000002023 wood Substances 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- -1 alkali metal salt Chemical class 0.000 claims abstract description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 239000004480 active ingredient Substances 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical class 0.000 claims abstract description 11
- 125000002541 furyl group Chemical group 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 229910052717 sulfur Chemical group 0.000 claims abstract description 9
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 239000011593 sulfur Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 5
- 238000004321 preservation Methods 0.000 claims description 5
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 2
- 230000002538 fungal effect Effects 0.000 description 48
- 241000233866 Fungi Species 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 206010017533 Fungal infection Diseases 0.000 description 12
- 208000031888 Mycoses Diseases 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 206010061217 Infestation Diseases 0.000 description 8
- 239000013543 active substance Substances 0.000 description 8
- 229920001817 Agar Polymers 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 241000228245 Aspergillus niger Species 0.000 description 6
- 241000223678 Aureobasidium pullulans Species 0.000 description 6
- 241000223261 Trichoderma viride Species 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YGNKWPMTZSNPDA-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-5,6-dihydro-1,4,2-oxathiazine Chemical compound O1CCSC(C=2SC3=CC=CC=C3N=2)=N1 YGNKWPMTZSNPDA-UHFFFAOYSA-N 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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- 235000010099 Fagus sylvatica Nutrition 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
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- WCDMXJDFKIYKIO-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4-oxide Chemical compound O=S1CCON=C1C1=NC2=CC=CC=C2S1 WCDMXJDFKIYKIO-UHFFFAOYSA-N 0.000 description 3
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- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- AHBYLFUEUKTMRD-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4,4-dioxide Chemical compound O=S1(=O)CCON=C1C1=NC2=CC=CC=C2S1 AHBYLFUEUKTMRD-UHFFFAOYSA-N 0.000 description 2
- YOSDUYOUGMGRNL-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5,6-dihydro-1,4,2-oxathiazine Chemical compound S1C(Cl)=CC=C1C1=NOCCS1 YOSDUYOUGMGRNL-UHFFFAOYSA-N 0.000 description 2
- SPXXBJJWVDLKOU-UHFFFAOYSA-N 6-methyl-3-thiophen-2-yl-5,6-dihydro-1,4,2-oxathiazine Chemical compound O1C(C)CSC(C=2SC=CC=2)=N1 SPXXBJJWVDLKOU-UHFFFAOYSA-N 0.000 description 2
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
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- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
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- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
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- KCAPRLOTPQAKAQ-UHFFFAOYSA-N methyl 5-chlorothiophene-2-carbodithioate Chemical compound CSC(=S)C1=CC=C(Cl)S1 KCAPRLOTPQAKAQ-UHFFFAOYSA-N 0.000 description 1
- QTFGJYVLAVUFIX-UHFFFAOYSA-N methyl thiophene-2-carbodithioate Chemical compound CSC(=S)C1=CC=CS1 QTFGJYVLAVUFIX-UHFFFAOYSA-N 0.000 description 1
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- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11138693A | 1993-08-24 | 1993-08-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9600437D0 HU9600437D0 (en) | 1996-04-29 |
| HUT74480A HUT74480A (en) | 1997-01-28 |
| HU215235B true HU215235B (hu) | 1998-11-30 |
Family
ID=22338232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9600437A HU215235B (hu) | 1993-08-24 | 1994-08-24 | Fatartósító oxatiazinok, készítmények és alkalmazásuk |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US5777110A (enExample) |
| EP (1) | EP0715625B1 (enExample) |
| JP (1) | JP2761441B2 (enExample) |
| KR (1) | KR100335756B1 (enExample) |
| CN (1) | CN1059440C (enExample) |
| AT (1) | ATE154017T1 (enExample) |
| AU (1) | AU688371B2 (enExample) |
| BR (1) | BR9407561A (enExample) |
| CA (1) | CA2169654C (enExample) |
| CZ (1) | CZ291537B6 (enExample) |
| DE (1) | DE69403667T2 (enExample) |
| DK (1) | DK0715625T3 (enExample) |
| ES (1) | ES2102878T3 (enExample) |
| FI (1) | FI119512B (enExample) |
| GR (1) | GR3024590T3 (enExample) |
| HU (1) | HU215235B (enExample) |
| MX (1) | MX9406411A (enExample) |
| MY (1) | MY137123A (enExample) |
| NO (1) | NO305837B1 (enExample) |
| NZ (1) | NZ273187A (enExample) |
| PL (1) | PL180262B1 (enExample) |
| RU (1) | RU2127266C1 (enExample) |
| TW (1) | TW279784B (enExample) |
| WO (1) | WO1995006043A1 (enExample) |
| ZA (1) | ZA946450B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0823461A1 (en) * | 1996-08-07 | 1998-02-11 | Sigma Coatings B.V. | Increasing the self-polishing properties of antifouling paints |
| JP2001519365A (ja) * | 1997-10-15 | 2001-10-23 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | オキサチアジンおよびベンゾチオフェン−２−カルボキサミド−ｓ，ｓ−ジオキシドを含んでなる相乗作用性組成物 |
| US5965749A (en) * | 1998-03-16 | 1999-10-12 | Uniroyal Chemical Company, Inc. | Process for synthesizing substituted 2-benzo [b]thiophenecarboxylic acids and salts thereof |
| GB9826245D0 (en) * | 1998-11-30 | 1999-01-20 | Hickson Int Plc | Wood preserative formulations |
| US20060160791A1 (en) * | 1999-11-30 | 2006-07-20 | Gareth Williams | Wood preservative formulations |
| JP2002265310A (ja) * | 2001-03-06 | 2002-09-18 | Nagase Chemtex Corp | 抗微生物剤組成物 |
| CN1269401C (zh) | 2001-11-08 | 2006-08-16 | 詹森药业有限公司 | 含有4—溴—2—(4—氯苯基)—5—(三氟甲基)—1h—吡咯—3—腈的增效性抗污臭组合物 |
| CA2493922A1 (en) | 2002-07-26 | 2004-02-05 | Osmose, Inc. | Polymeric wood preservative compositions |
| US8637089B2 (en) * | 2003-04-09 | 2014-01-28 | Osmose, Inc. | Micronized wood preservative formulations |
| KR101110669B1 (ko) | 2003-04-09 | 2012-02-17 | 오스모스 인코포레이티드 | 미세화된 목재 방부제 제형 |
| US6960669B2 (en) | 2003-09-10 | 2005-11-01 | Crompton Co./Cie | Utilization of phosphorus pentasulfide in thionylations using phase transfer catalysis |
| AU2006272838A1 (en) * | 2005-07-21 | 2007-02-01 | Osmose, Inc. | Compositions and methods for wood preservation |
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| US20090162410A1 (en) * | 2007-12-21 | 2009-06-25 | Jun Zhang | Process for preparing fine particle dispersion for wood preservation |
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1994
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