CN100537551C - 作为杀虫剂的被噻唑基取代的碳环1,3-二酮类化合物 - Google Patents
作为杀虫剂的被噻唑基取代的碳环1,3-二酮类化合物 Download PDFInfo
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- CN100537551C CN100537551C CNB2006100956330A CN200610095633A CN100537551C CN 100537551 C CN100537551 C CN 100537551C CN B2006100956330 A CNB2006100956330 A CN B2006100956330A CN 200610095633 A CN200610095633 A CN 200610095633A CN 100537551 C CN100537551 C CN 100537551C
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- alkyl
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- alkoxy
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- ethyl
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- 239000002917 insecticide Substances 0.000 title claims description 8
- 125000002837 carbocyclic group Chemical class 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 96
- 239000004009 herbicide Substances 0.000 claims abstract description 7
- 239000000417 fungicide Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 267
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims description 213
- 239000001257 hydrogen Substances 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 238000002360 preparation method Methods 0.000 claims description 93
- 239000000460 chlorine Substances 0.000 claims description 92
- 239000011737 fluorine Substances 0.000 claims description 86
- 229910052731 fluorine Inorganic materials 0.000 claims description 86
- 229910052760 oxygen Inorganic materials 0.000 claims description 86
- 239000001301 oxygen Substances 0.000 claims description 82
- 229910052801 chlorine Inorganic materials 0.000 claims description 81
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 74
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 70
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 62
- 150000002367 halogens Chemical group 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 50
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 46
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 44
- 229910052794 bromium Inorganic materials 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
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- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
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- 239000011230 binding agent Substances 0.000 claims description 29
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
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- 125000004076 pyridyl group Chemical group 0.000 claims description 8
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
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- 150000002431 hydrogen Chemical group 0.000 claims 37
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 15
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- 239000003085 diluting agent Substances 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 1
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- LRYSUGTXBIPBGB-UHFFFAOYSA-N chloromethanedithioic acid Chemical compound SC(Cl)=S LRYSUGTXBIPBGB-UHFFFAOYSA-N 0.000 claims 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical compound CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- 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
- A01N43/74—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10118310.0 | 2001-04-12 | ||
| DE10118310A DE10118310A1 (de) | 2001-04-12 | 2001-04-12 | Hetarylsubstituierte carbocyclische 1,3-Dione |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028116569A Division CN1272329C (zh) | 2001-04-12 | 2002-04-02 | 作为杀虫剂的被噻唑基取代的碳环1,3－二酮类化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1880308A CN1880308A (zh) | 2006-12-20 |
| CN100537551C true CN100537551C (zh) | 2009-09-09 |
Family
ID=7681383
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2006100956330A Expired - Fee Related CN100537551C (zh) | 2001-04-12 | 2002-04-02 | 作为杀虫剂的被噻唑基取代的碳环1,3-二酮类化合物 |
| CNB028116569A Expired - Fee Related CN1272329C (zh) | 2001-04-12 | 2002-04-02 | 作为杀虫剂的被噻唑基取代的碳环1,3－二酮类化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028116569A Expired - Fee Related CN1272329C (zh) | 2001-04-12 | 2002-04-02 | 作为杀虫剂的被噻唑基取代的碳环1,3－二酮类化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7595404B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1381596B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4413497B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100862892B1 (cg-RX-API-DMAC7.html) |
| CN (2) | CN100537551C (cg-RX-API-DMAC7.html) |
| AR (1) | AR035454A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE340787T1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0209082B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2443642C (cg-RX-API-DMAC7.html) |
| DE (2) | DE10118310A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1381596T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2271332T3 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA03009315A (cg-RX-API-DMAC7.html) |
| PL (1) | PL364391A1 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2306310C2 (cg-RX-API-DMAC7.html) |
| UA (1) | UA76749C2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002088098A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7338969B2 (en) * | 2002-03-08 | 2008-03-04 | Quonova, Llc | Modulation of pathogenicity |
| DE10331675A1 (de) * | 2003-07-14 | 2005-02-10 | Bayer Cropscience Ag | Hetarylsubstituierte Pyrazolidindion-Derivate |
| GB0704652D0 (en) | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
| GB0714981D0 (en) * | 2007-08-01 | 2007-09-12 | Syngenta Ltd | Novel herbicides |
| GB0717082D0 (en) * | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
| GB0819205D0 (en) | 2008-10-20 | 2008-11-26 | Syngenta Ltd | Novel herbicides |
| CN102471311B (zh) * | 2009-07-31 | 2016-04-27 | 辛根塔有限公司 | 除草活性的杂芳基取代的环二酮或其衍生物 |
| WO2013021044A1 (de) | 2011-08-11 | 2013-02-14 | Bayer Intellectual Property Gmbh | 1,2,4-triazolyl-substituierte ketoenole |
| IL310022B2 (en) * | 2021-07-12 | 2024-11-01 | Fortephest Ltd | Novel derivatives of non-coded amino acids and their use as herbicides |
| CN116196314B (zh) * | 2023-05-04 | 2023-08-15 | 广州市妇女儿童医疗中心 | Ri-1或其盐在制备防治胃肠道疾病的药物中的应用 |
| CN116589393A (zh) * | 2023-05-19 | 2023-08-15 | 开封博凯生物化工有限公司 | 以二正丁胺为缚酸剂生产溴虫腈的工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130759C (cg-RX-API-DMAC7.html) | 1965-10-07 | |||
| PT67818A (en) | 1977-03-28 | 1978-04-01 | Union Carbide Corp | Process for the synthesis of biocidal 2-aryl-1,3-cycloalkanedionas and their enol esters |
| US4659372A (en) * | 1977-03-28 | 1987-04-21 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds |
| CN1003445B (zh) | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| GB8826035D0 (en) | 1988-11-07 | 1988-12-14 | Ici Plc | Herbicidal compositions |
-
2001
- 2001-04-12 DE DE10118310A patent/DE10118310A1/de not_active Withdrawn
-
2002
- 2002-02-04 UA UA20031110185A patent/UA76749C2/uk unknown
- 2002-04-02 KR KR1020037013128A patent/KR100862892B1/ko not_active Expired - Fee Related
- 2002-04-02 RU RU2003133144/04A patent/RU2306310C2/ru not_active IP Right Cessation
- 2002-04-02 PL PL02364391A patent/PL364391A1/xx not_active Application Discontinuation
- 2002-04-02 DE DE50208258T patent/DE50208258D1/de not_active Expired - Lifetime
- 2002-04-02 DK DK02766566T patent/DK1381596T3/da active
- 2002-04-02 US US10/474,308 patent/US7595404B2/en not_active Expired - Fee Related
- 2002-04-02 EP EP02766566A patent/EP1381596B1/de not_active Expired - Lifetime
- 2002-04-02 CA CA2443642A patent/CA2443642C/en not_active Expired - Fee Related
- 2002-04-02 MX MXPA03009315A patent/MXPA03009315A/es active IP Right Grant
- 2002-04-02 JP JP2002585400A patent/JP4413497B2/ja not_active Expired - Fee Related
- 2002-04-02 AT AT02766566T patent/ATE340787T1/de not_active IP Right Cessation
- 2002-04-02 CN CNB2006100956330A patent/CN100537551C/zh not_active Expired - Fee Related
- 2002-04-02 WO PCT/EP2002/003620 patent/WO2002088098A1/de not_active Ceased
- 2002-04-02 BR BRPI0209082-1A patent/BR0209082B1/pt not_active IP Right Cessation
- 2002-04-02 ES ES02766566T patent/ES2271332T3/es not_active Expired - Lifetime
- 2002-04-02 CN CNB028116569A patent/CN1272329C/zh not_active Expired - Fee Related
- 2002-04-05 AR ARP020101269A patent/AR035454A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002088098A1 (de) | 2002-11-07 |
| US20070135630A1 (en) | 2007-06-14 |
| KR100862892B1 (ko) | 2008-10-13 |
| CA2443642A1 (en) | 2002-11-07 |
| PL364391A1 (en) | 2004-12-13 |
| US7595404B2 (en) | 2009-09-29 |
| AR035454A1 (es) | 2004-05-26 |
| RU2003133144A (ru) | 2005-05-10 |
| CN1272329C (zh) | 2006-08-30 |
| EP1381596B1 (de) | 2006-09-27 |
| BR0209082A (pt) | 2004-08-10 |
| KR20040067869A (ko) | 2004-07-30 |
| RU2306310C2 (ru) | 2007-09-20 |
| DK1381596T3 (da) | 2007-02-05 |
| DE10118310A1 (de) | 2002-10-17 |
| BR0209082B1 (pt) | 2014-10-07 |
| CA2443642C (en) | 2011-03-08 |
| ATE340787T1 (de) | 2006-10-15 |
| EP1381596A1 (de) | 2004-01-21 |
| JP2004528350A (ja) | 2004-09-16 |
| UA76749C2 (uk) | 2006-09-15 |
| CN1880308A (zh) | 2006-12-20 |
| DE50208258D1 (de) | 2006-11-09 |
| MXPA03009315A (es) | 2004-02-12 |
| JP4413497B2 (ja) | 2010-02-10 |
| ES2271332T3 (es) | 2007-04-16 |
| CN1514830A (zh) | 2004-07-21 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20090909 Termination date: 20110402 |