JP5571062B2 - 殺真菌剤ヒドロキシモイル−テトラゾール誘導体 - Google Patents
殺真菌剤ヒドロキシモイル−テトラゾール誘導体 Download PDFInfo
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- JP5571062B2 JP5571062B2 JP2011500217A JP2011500217A JP5571062B2 JP 5571062 B2 JP5571062 B2 JP 5571062B2 JP 2011500217 A JP2011500217 A JP 2011500217A JP 2011500217 A JP2011500217 A JP 2011500217A JP 5571062 B2 JP5571062 B2 JP 5571062B2
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- unsubstituted
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- alkyl
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- 125000005843 halogen group Chemical group 0.000 claims description 136
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 18
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- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 11
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 9
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000000033 alkoxyamino group Chemical group 0.000 claims 2
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
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- 238000004587 chromatography analysis Methods 0.000 description 29
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- 229910002091 carbon monoxide Inorganic materials 0.000 description 23
- 239000010410 layer Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 240000008042 Zea mays Species 0.000 description 16
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 16
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 16
- 235000005822 corn Nutrition 0.000 description 16
- 230000000749 insecticidal effect Effects 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
- 102000004190 Enzymes Human genes 0.000 description 15
- 108090000790 Enzymes Proteins 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- 239000012267 brine Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
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- 239000004009 herbicide Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- 230000009261 transgenic effect Effects 0.000 description 11
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- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
-
- 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
- C07D417/14—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 three or more hetero rings
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08356047 | 2008-03-19 | ||
| EP08356047.4 | 2008-03-19 | ||
| PCT/EP2009/053208 WO2009115557A2 (en) | 2008-03-19 | 2009-03-18 | Fungicide hydroximoyl-tetrazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011520778A JP2011520778A (ja) | 2011-07-21 |
| JP2011520778A5 JP2011520778A5 (https=) | 2011-09-15 |
| JP5571062B2 true JP5571062B2 (ja) | 2014-08-13 |
Family
ID=39673452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011500217A Expired - Fee Related JP5571062B2 (ja) | 2008-03-19 | 2009-03-18 | 殺真菌剤ヒドロキシモイル−テトラゾール誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8466176B2 (https=) |
| EP (1) | EP2265118A2 (https=) |
| JP (1) | JP5571062B2 (https=) |
| KR (1) | KR20100125424A (https=) |
| CN (1) | CN101977504B (https=) |
| BR (1) | BRPI0906023A2 (https=) |
| CO (1) | CO6280584A2 (https=) |
| MX (1) | MX2010010135A (https=) |
| WO (1) | WO2009115557A2 (https=) |
| ZA (1) | ZA201006312B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2234489B1 (en) * | 2008-01-15 | 2017-04-12 | Bayer Intellectual Property GmbH | Pesticide composition comprising a tetrazolyloxime derivative and a fungicide or an insecticide active substance |
| JP2011515368A (ja) * | 2008-03-19 | 2011-05-19 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺菌剤ヒドロキシモイル−テトラゾール誘導体 |
| EP2265119A1 (en) * | 2008-03-19 | 2010-12-29 | Bayer CropScience AG | Fungicide hydroximoyl-tetrazole derivatives |
| JP5524200B2 (ja) * | 2008-07-04 | 2014-06-18 | バイエル・クロップサイエンス・アーゲー | 殺真菌剤ヒドロキシモイル−テトラゾール誘導体 |
| KR20110030663A (ko) * | 2008-07-04 | 2011-03-23 | 바이엘 크롭사이언스 아게 | 살진균제 히드록시모일-테트라졸 유도체 |
| JP5550913B2 (ja) * | 2009-01-05 | 2014-07-16 | 日本曹達株式会社 | テトラゾイルオキシム誘導体およびその塩、並びに植物病害防除剤 |
| JP5542452B2 (ja) * | 2009-01-05 | 2014-07-09 | 日本曹達株式会社 | テトラゾイルオキシム誘導体およびその塩、ならびに植物病害防除剤 |
| EP2519103B1 (en) * | 2009-12-28 | 2014-08-13 | Bayer Intellectual Property GmbH | Fungicide hydroximoyl-tetrazole derivatives |
| BR122017023123B1 (pt) * | 2010-03-12 | 2018-04-24 | Nippon Soda Co., Ltd. | Método para produzir derivado de picolina halogenada |
| BR122017022932B1 (pt) | 2010-04-06 | 2018-05-15 | Nippon Soda Co., Ltd. | Método de produção de composto heterocíclico que contém nitrogênio |
| AU2014201037B9 (en) * | 2010-04-06 | 2015-11-19 | Nippon Soda Co., Ltd. | Nitrogen-containing heterocyclic compound and method for producing same |
| WO2011134911A2 (en) * | 2010-04-28 | 2011-11-03 | Bayer Cropscience Ag | Fungicide hydroximoyl-tetrazole derivatives |
| RS58401B1 (sr) * | 2010-10-07 | 2019-04-30 | Bayer Cropscience Ag | Sastav fungicida koji sadrži derivat tetrazoliloksima i derivat tiazolilpiperidina |
| WO2012117021A2 (en) * | 2011-03-03 | 2012-09-07 | Syngenta Participations Ag | Novel microbiocidal oxime ethers |
| JP5740042B2 (ja) * | 2012-03-13 | 2015-06-24 | 日本曹達株式会社 | 化合物、化合物の製造方法、及び化合物の精製方法 |
| WO2014136603A1 (ja) * | 2013-03-05 | 2014-09-12 | 日本曹達株式会社 | 卵菌類以外の植物病原性糸状菌を防除する方法 |
| CN107889486B (zh) | 2015-07-28 | 2021-07-09 | 日本曹达株式会社 | 吡啶-2-基吡啶化合物及其使用方法 |
| BR122022025232B1 (pt) | 2016-10-10 | 2023-10-31 | Basf Se | Mistura pesticida, composição pesticida, métodos para controlar pragas fitopatogênicas, para melhorar a saúde de plantas e para a proteção do material de propagação vegetal contra pragas e material de propagação vegetal |
| WO2018069110A1 (en) | 2016-10-10 | 2018-04-19 | Basf Se | Pesticidal mixtures |
| WO2018069108A1 (en) | 2016-10-10 | 2018-04-19 | Basf Se | Pesticidal mixtures |
| MX2021010111A (es) | 2019-02-20 | 2021-09-21 | Basf Se | Mezclas plaguicidas que comprenden un compuesto de pirazol. |
| CN112110911B (zh) * | 2019-06-19 | 2024-04-26 | 东莞市东阳光农药研发有限公司 | 1,3,4-噁二唑类肟衍生物及其制备方法和应用 |
| KR102345734B1 (ko) | 2019-06-21 | 2021-12-31 | 주식회사 라파스 | 최소 침습적 바이오 센싱을 위한 생체적합성이고 전기전도성인 고분자 마이크로니들 바이오 센서 |
| CN112979633B (zh) * | 2019-12-12 | 2024-02-02 | 东莞市东阳光农药研发有限公司 | 新的肟类衍生物及其制备方法和应用 |
| CN112979628B (zh) * | 2019-12-12 | 2024-04-26 | 东莞市东阳光农药研发有限公司 | 二苯醚取代的肟类衍生物及其在农业中的应用 |
| CN114685392A (zh) * | 2020-12-28 | 2022-07-01 | 东莞市东阳光农药研发有限公司 | 一种苯基-四唑肟类衍生物及其制备方法和应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2581063B1 (fr) * | 1985-04-30 | 1987-07-17 | Chauvin Blache Lab | Amino-2 thiazoles n-substitues, leur procede de preparation et leur application en therapeutique |
| US4933355A (en) * | 1988-04-14 | 1990-06-12 | Sankyo Company Limited | Thiazole derivatives, their preparation and their use in the treatment of diabetes complications |
| FR2687149B1 (fr) * | 1992-02-12 | 1995-11-03 | Roussel Uclaf | Nouveaux esters pyrethrinouides derives d'alcools thiazoliques, leur procede de preparation et leur application comme pesticides. |
| US5455351A (en) * | 1993-12-13 | 1995-10-03 | Abbott Laboratories | Retroviral protease inhibiting piperazine compounds |
| NZ505002A (en) * | 1997-12-10 | 2001-11-30 | Dainippon Ink & Chemicals | 1,2,5-oxadiazolyl, 1,2,5-thiadiazolyl or 1,2,3-thiadiazolyl oxime derivatives substituted by another heterocyclic group useful as agricultural chemicals |
| US6472386B1 (en) * | 2001-06-29 | 2002-10-29 | Kowa Co., Ltd. | Cyclic diamine compound with 5-membered ring groups |
| AR035087A1 (es) | 2001-08-09 | 2004-04-14 | Syngenta Participations Ag | Piridil-alquinos y piridil-n-oxido-alquinos herbicidas activos, procedimiento para su preparacion, composicion herbicida y para inhibir el crecimiento de plantas, metodo para el control del crecimiento de plantas indeseables , y metodo para la inhibicion del crecimiento de plantas |
| JP4330313B2 (ja) * | 2001-08-20 | 2009-09-16 | 日本曹達株式会社 | テトラゾイルオキシム誘導体及びこれを有効成分とする農薬 |
| US7183299B2 (en) * | 2001-08-20 | 2007-02-27 | Nippon Soda Co., Ltd. | Tetrazoyl oxime derivative and agricultural chemical containing the same as active ingredient |
| AR037754A1 (es) | 2001-12-11 | 2004-12-01 | Syngenta Participations Ag | Herbicidas |
| JP2004131392A (ja) * | 2002-10-08 | 2004-04-30 | Sumitomo Chem Co Ltd | テトラゾール化合物およびその用途 |
| JP2004131416A (ja) * | 2002-10-10 | 2004-04-30 | Sumitomo Chem Co Ltd | テトラゾール化合物およびその植物病害防除用途 |
| US20060205740A1 (en) | 2003-08-14 | 2006-09-14 | Reno Michael J | Chemical compounds |
| DE102004016845A1 (de) * | 2004-04-07 | 2005-10-27 | Bayer Healthcare Ag | Phenylthioessigsäure-Derivate und ihre Verwendung |
| TWI346109B (en) * | 2004-04-30 | 2011-08-01 | Otsuka Pharma Co Ltd | 4-amino-5-cyanopyrimidine derivatives |
| KR20090031619A (ko) * | 2006-07-13 | 2009-03-26 | 바이엘 크롭사이언스 소시에떼아노님 | 살진균제 히드록시모일-테트라졸 유도체 |
| MX2009000299A (es) * | 2006-07-13 | 2009-01-26 | Bayer Cropscience Sa | Derivados de hidroximoil-tetrazol fungicidas. |
| CA2653589A1 (en) * | 2006-07-13 | 2008-01-17 | Bayer Cropscience Sa | Fungicide hydroximoyl-tetrazole derivatives |
| US8084613B2 (en) | 2007-05-14 | 2011-12-27 | Nippon Soda Co., Ltd. | Tetrazoyloxime derivative and plant disease control agent |
| KR101327670B1 (ko) * | 2007-08-08 | 2013-11-08 | 닛뽕소다 가부시키가이샤 | 테트라조일옥심 유도체 및 식물 병해 방제제 |
| RU2010133984A (ru) * | 2008-01-16 | 2012-02-27 | Байер КропСайенс АГ (DE) | Фунгицидные производные гидроксимоилтетразола |
-
2009
- 2009-03-18 KR KR1020107023225A patent/KR20100125424A/ko not_active Withdrawn
- 2009-03-18 WO PCT/EP2009/053208 patent/WO2009115557A2/en not_active Ceased
- 2009-03-18 EP EP09721227A patent/EP2265118A2/en not_active Withdrawn
- 2009-03-18 BR BRPI0906023-5A patent/BRPI0906023A2/pt not_active IP Right Cessation
- 2009-03-18 JP JP2011500217A patent/JP5571062B2/ja not_active Expired - Fee Related
- 2009-03-18 MX MX2010010135A patent/MX2010010135A/es active IP Right Grant
- 2009-03-18 CN CN200980109889.4A patent/CN101977504B/zh not_active Expired - Fee Related
- 2009-03-18 US US12/933,276 patent/US8466176B2/en not_active Expired - Fee Related
-
2010
- 2010-09-02 ZA ZA2010/06312A patent/ZA201006312B/en unknown
- 2010-09-15 CO CO10114368A patent/CO6280584A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011520778A (ja) | 2011-07-21 |
| US8466176B2 (en) | 2013-06-18 |
| WO2009115557A3 (en) | 2009-11-26 |
| BRPI0906023A2 (pt) | 2015-06-30 |
| MX2010010135A (es) | 2010-10-25 |
| CO6280584A2 (es) | 2011-05-20 |
| KR20100125424A (ko) | 2010-11-30 |
| CN101977504B (zh) | 2014-11-26 |
| EP2265118A2 (en) | 2010-12-29 |
| CN101977504A (zh) | 2011-02-16 |
| WO2009115557A2 (en) | 2009-09-24 |
| ZA201006312B (en) | 2013-02-27 |
| US20110105566A1 (en) | 2011-05-05 |
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