RU2127266C1 - Соединение оксатиазина, способ защиты древесины или композиционных древесных материалов, композиция для защиты древесины или композиционного древесного материала - Google Patents
Соединение оксатиазина, способ защиты древесины или композиционных древесных материалов, композиция для защиты древесины или композиционного древесного материала Download PDFInfo
- Publication number
- RU2127266C1 RU2127266C1 RU96105384A RU96105384A RU2127266C1 RU 2127266 C1 RU2127266 C1 RU 2127266C1 RU 96105384 A RU96105384 A RU 96105384A RU 96105384 A RU96105384 A RU 96105384A RU 2127266 C1 RU2127266 C1 RU 2127266C1
- Authority
- RU
- Russia
- Prior art keywords
- hydrogen
- alkyl
- alkoxy
- wood
- phenyl
- Prior art date
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- -1 Oxathiazine compound Chemical class 0.000 title claims abstract description 105
- 239000002023 wood Substances 0.000 title claims abstract description 56
- 239000000203 mixture Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000002131 composite material Substances 0.000 claims description 10
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 230000000855 fungicidal effect Effects 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 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
- NNNHOGSGWHUERV-UHFFFAOYSA-N OC(=O)CC(Cl)Br Chemical compound OC(=O)CC(Cl)Br NNNHOGSGWHUERV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-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
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 2
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 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 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 238000003786 synthesis reaction Methods 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 10
- 239000010875 treated wood Substances 0.000 abstract description 5
- 230000009931 harmful effect Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 241000233866 Fungi Species 0.000 description 42
- 238000012360 testing method Methods 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000002538 fungal effect Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
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- 229920001817 Agar Polymers 0.000 description 7
- 239000008272 agar Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 230000035784 germination Effects 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
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- 241001070947 Fagus Species 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
- 238000011156 evaluation Methods 0.000 description 4
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- 239000003755 preservative agent Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 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 3
- 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 3
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- 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
- 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 2
- QPAACYVYXIHGMJ-UHFFFAOYSA-N 3-(5-chlorothiophen-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4,4-dioxide Chemical compound S1C(Cl)=CC=C1C1=NOCCS1(=O)=O QPAACYVYXIHGMJ-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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- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 2
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- AKNQMEBLVAMSNZ-UHFFFAOYSA-N azaconazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2N=CN=C2)OCCO1 AKNQMEBLVAMSNZ-UHFFFAOYSA-N 0.000 description 1
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- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
- 239000003171 wood protecting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11138693A | 1993-08-24 | 1993-08-24 | |
| US111386 | 1993-08-24 | ||
| PCT/US1994/009702 WO1995006043A1 (en) | 1993-08-24 | 1994-08-24 | Wood preservative oxathiazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96105384A RU96105384A (ru) | 1998-06-10 |
| RU2127266C1 true RU2127266C1 (ru) | 1999-03-10 |
Family
ID=22338232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96105384A RU2127266C1 (ru) | 1993-08-24 | 1994-08-24 | Соединение оксатиазина, способ защиты древесины или композиционных древесных материалов, композиция для защиты древесины или композиционного древесного материала |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2400069C1 (ru) * | 2009-06-11 | 2010-09-27 | Галина Ивановна Эль-Регистан | Способ защиты материалов от микробного разрушения |
Families Citing this family (20)
| 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 |
| EP1022949A1 (en) | 1997-10-15 | 2000-08-02 | Janssen Pharmaceutica N.V. | Synergistic compositions comprising an oxathiazine and a benzothiophene-2-carboxamide-s,s-dioxide |
| 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 |
| EP2036439A3 (en) | 2001-11-08 | 2009-06-24 | Janssen Pharmaceutica N.V. | Synergistic antifouling compositions comprising 4-bromo-2-(4 chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile |
| EP1545205A4 (en) * | 2002-07-26 | 2008-07-02 | Osmose Inc | POLYMER WOOD PROTECTION |
| 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 |
| US20100068545A1 (en) * | 2005-07-21 | 2010-03-18 | Jun Zhang | Compositions and methods for wood preservation |
| TWI486122B (zh) | 2006-02-01 | 2015-06-01 | Janssen Pharmaceutica Nv | ４-溴-２-（４-氯苯基）-５-（三氟甲基）-１ｈ-吡咯-３-腈及金屬化合物之組合物 |
| DE602007003105D1 (de) | 2006-08-07 | 2009-12-17 | Janssen Pharmaceutica Nv | Kombinationen aus 4-brom-2-(4-chlorphenyl)-5-(trifluormethyl)-1h-pyrrol-3-carbonitril und oxidierungsmitteln |
| US20080175913A1 (en) * | 2007-01-09 | 2008-07-24 | Jun Zhang | Wood preservative compositions comprising isothiazolone-pyrethroids |
| US20090162410A1 (en) * | 2007-12-21 | 2009-06-25 | Jun Zhang | Process for preparing fine particle dispersion for wood preservation |
| EP2576532B1 (en) | 2010-06-07 | 2018-07-18 | Novomedix, LLC | Furanyl compounds and the use thereof |
| US20120142676A1 (en) | 2010-08-18 | 2012-06-07 | Gaik-Lean Chee | Oxathiazine and dithiine oxides as inhibitors of sulfhydryl-dependent biomolecules |
| CN102783502B (zh) * | 2012-08-22 | 2014-02-19 | 福建师范大学 | 一种竹材和竹制品专用防霉菌剂的制备及其应用 |
| CN107379175A (zh) * | 2017-09-07 | 2017-11-24 | 阜南县大自然工艺品有限公司 | 一种榆木工艺品的加工方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0104940A1 (en) * | 1982-09-28 | 1984-04-04 | Uniroyal, Inc. | 3-Aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
| US4562185A (en) * | 1983-03-30 | 1985-12-31 | Bayer Aktiengesellschaft | Five-membered nitrogen-containing hetero-cyclic compounds and their use as pest-combating agents |
| US4569690A (en) * | 1982-09-28 | 1986-02-11 | Uniroyal, Inc. | 3-Aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
| SU1288062A1 (ru) * | 1984-12-10 | 1987-02-07 | Научно-Производственное Объединение "Силава" | Ингибитор биоразрушени древесины |
| EP0363316A1 (de) * | 1988-09-30 | 1990-04-11 | Ciba-Geigy Ag | Biocide für den Materialschutz und für Wassersysteme |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691015A (en) * | 1951-01-09 | 1954-10-05 | Goodrich Co B F | N-(4-thiazolinyl-2) sulfenimides |
| DE2001017C3 (de) * | 1970-01-10 | 1978-05-18 | Hoechst Ag, 6000 Frankfurt | 3,4-Dihydro-1,23-oxathiazin-4on-2,2-dioxide, ihre Herstellung und Verwendung |
| US4376513A (en) * | 1980-06-30 | 1983-03-15 | The Toro Company | Irrigation stream splitter |
| US4675044A (en) * | 1982-09-28 | 1987-06-23 | Uniroyal Chemical Company, Inc. | 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
| CA1257451A (en) * | 1985-11-25 | 1989-07-18 | William P. Trumble | Stabilization of wood preservative solutions and preservation of wood by such solutions |
| DE3641555A1 (de) * | 1986-12-05 | 1988-06-16 | Solvay Werke Gmbh | Mittel oder konzentrat zum konservieren von holz und holzwerkstoffen |
| US5135927A (en) * | 1987-01-30 | 1992-08-04 | Ciba-Geigy Corporation | Microbicidal composition |
| US4977186A (en) * | 1988-11-23 | 1990-12-11 | Troy Chemical Corporation | Wood preservative and soil treatment composition |
| AP9500775A0 (en) * | 1993-08-24 | 1996-01-31 | Janssen Pharmaceutica Nv | Antibacterial and antifouling oxathiazines and their oxides |
-
1994
- 1994-08-23 MY MYPI94002201A patent/MY137123A/en unknown
- 1994-08-23 MX MX9406411A patent/MX9406411A/es not_active IP Right Cessation
- 1994-08-24 US US08/295,117 patent/US5777110A/en not_active Expired - Lifetime
- 1994-08-24 AT AT94926617T patent/ATE154017T1/de active
- 1994-08-24 EP EP94926617A patent/EP0715625B1/en not_active Expired - Lifetime
- 1994-08-24 JP JP7507780A patent/JP2761441B2/ja not_active Expired - Fee Related
- 1994-08-24 BR BR9407561A patent/BR9407561A/pt not_active IP Right Cessation
- 1994-08-24 KR KR1019960700888A patent/KR100335756B1/ko not_active Expired - Fee Related
- 1994-08-24 ZA ZA946450A patent/ZA946450B/xx unknown
- 1994-08-24 WO PCT/US1994/009702 patent/WO1995006043A1/en not_active Ceased
- 1994-08-24 ES ES94926617T patent/ES2102878T3/es not_active Expired - Lifetime
- 1994-08-24 AU AU76401/94A patent/AU688371B2/en not_active Ceased
- 1994-08-24 CN CN94193747A patent/CN1059440C/zh not_active Expired - Fee Related
- 1994-08-24 NZ NZ273187A patent/NZ273187A/en not_active IP Right Cessation
- 1994-08-24 RU RU96105384A patent/RU2127266C1/ru not_active IP Right Cessation
- 1994-08-24 CZ CZ1996560A patent/CZ291537B6/cs not_active IP Right Cessation
- 1994-08-24 DK DK94926617.5T patent/DK0715625T3/da active
- 1994-08-24 PL PL94313136A patent/PL180262B1/pl not_active IP Right Cessation
- 1994-08-24 DE DE69403667T patent/DE69403667T2/de not_active Expired - Lifetime
- 1994-08-24 CA CA002169654A patent/CA2169654C/en not_active Expired - Fee Related
- 1994-08-24 HU HU9600437A patent/HU215235B/hu not_active IP Right Cessation
- 1994-09-22 TW TW083108750A patent/TW279784B/zh not_active IP Right Cessation
-
1996
- 1996-02-21 NO NO960696A patent/NO305837B1/no not_active IP Right Cessation
- 1996-02-23 FI FI960829A patent/FI119512B/fi not_active IP Right Cessation
-
1997
- 1997-09-02 GR GR970402234T patent/GR3024590T3/el unknown
- 1997-11-12 US US08/967,856 patent/US6372297B1/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0104940A1 (en) * | 1982-09-28 | 1984-04-04 | Uniroyal, Inc. | 3-Aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
| US4569690A (en) * | 1982-09-28 | 1986-02-11 | Uniroyal, Inc. | 3-Aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides |
| US4562185A (en) * | 1983-03-30 | 1985-12-31 | Bayer Aktiengesellschaft | Five-membered nitrogen-containing hetero-cyclic compounds and their use as pest-combating agents |
| SU1288062A1 (ru) * | 1984-12-10 | 1987-02-07 | Научно-Производственное Объединение "Силава" | Ингибитор биоразрушени древесины |
| EP0363316A1 (de) * | 1988-09-30 | 1990-04-11 | Ciba-Geigy Ag | Biocide für den Materialschutz und für Wassersysteme |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2400069C1 (ru) * | 2009-06-11 | 2010-09-27 | Галина Ивановна Эль-Регистан | Способ защиты материалов от микробного разрушения |
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| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20120825 |