TW201014529A - Thiadiazolyloxyphenylamidines and the use thereof as fungicides - Google Patents
Thiadiazolyloxyphenylamidines and the use thereof as fungicides Download PDFInfo
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- TW201014529A TW201014529A TW098121496A TW98121496A TW201014529A TW 201014529 A TW201014529 A TW 201014529A TW 098121496 A TW098121496 A TW 098121496A TW 98121496 A TW98121496 A TW 98121496A TW 201014529 A TW201014529 A TW 201014529A
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- Prior art keywords
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- oxy
- formula
- thiadiazol
- alkyl
- Prior art date
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- 239000000417 fungicide Substances 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 41
- 244000005700 microbiome Species 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 9
- 150000001409 amidines Chemical class 0.000 claims abstract 2
- -1 thiadiazoleoxyphenyl hydrazine Chemical compound 0.000 claims description 132
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 125000004122 cyclic group Chemical group 0.000 claims description 48
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 239000007789 gas Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims description 21
- 150000003573 thiols Chemical class 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 150000003568 thioethers Chemical class 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 239000002689 soil Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 150000002429 hydrazines Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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- 150000002905 orthoesters Chemical class 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 7
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 6
- OUMYCZNNPRRSLG-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-trien-5-amine Chemical compound NC1=CC=CC2=C1O2 OUMYCZNNPRRSLG-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 4
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- 125000003944 tolyl group Chemical group 0.000 claims description 3
- XVIRIXVOLLJIPF-UHFFFAOYSA-N 1-nitro-2-(2-nitrophenoxy)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=CC=C1[N+]([O-])=O XVIRIXVOLLJIPF-UHFFFAOYSA-N 0.000 claims description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 2
- HDBQZGJWHMCXIL-UHFFFAOYSA-N 3,7-dihydropurine-2-thione Chemical compound SC1=NC=C2NC=NC2=N1 HDBQZGJWHMCXIL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
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- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 22
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- 150000003949 imides Chemical class 0.000 claims 2
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- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical class [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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- NGCRXXLKJAAUQQ-UHFFFAOYSA-N undec-5-ene Chemical compound CCCCCC=CCCCC NGCRXXLKJAAUQQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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
- A01N43/82—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 three ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08159265 | 2008-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201014529A true TW201014529A (en) | 2010-04-16 |
Family
ID=39878040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098121496A TW201014529A (en) | 2008-06-27 | 2009-06-26 | Thiadiazolyloxyphenylamidines and the use thereof as fungicides |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8383139B2 (https=) |
| EP (1) | EP2307391B1 (https=) |
| JP (1) | JP5713352B2 (https=) |
| CN (1) | CN102066347B (https=) |
| AR (1) | AR072373A1 (https=) |
| AU (1) | AU2009262515A1 (https=) |
| BR (1) | BRPI0914536A8 (https=) |
| CA (1) | CA2729432A1 (https=) |
| CL (1) | CL2010001530A1 (https=) |
| EA (1) | EA020256B9 (https=) |
| PL (1) | PL2307391T3 (https=) |
| TW (1) | TW201014529A (https=) |
| UA (1) | UA104293C2 (https=) |
| WO (1) | WO2009156098A2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102766110A (zh) * | 2005-09-13 | 2012-11-07 | 拜尔农科股份公司 | 农药噻唑氧基取代的苯脒衍生物 |
| WO2011082941A1 (de) * | 2009-12-16 | 2011-07-14 | Bayer Cropscience Ag | Benzylsubstituierte thiadiazolyloxyphenylamidiniumsalze als fungizide |
| WO2011080044A2 (en) | 2009-12-16 | 2011-07-07 | Bayer Cropscience Ag | Active compound combinations |
| WO2011156885A1 (en) * | 2010-06-17 | 2011-12-22 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture And Agri-Food | Use of psychrophilic anaerobic digestion in sequencing batch reactor for degradation of prions |
| WO2012019998A1 (de) | 2010-08-10 | 2012-02-16 | Bayer Cropscience Ag | Herstellung von n'-(4-{[3-(4-chlorbenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-n-ethyl-n-methylimidoformamid |
| ITMI20121045A1 (it) | 2012-06-15 | 2013-12-16 | Isagro Ricerca Srl | Composizioni sinergiche per la protezione di colture agrarie e relativo uso |
| CN115136961B (zh) | 2013-10-03 | 2024-11-19 | 先正达参股股份有限公司 | 杀真菌组合物 |
| CN104860938B (zh) * | 2015-06-08 | 2017-05-31 | 西华大学 | 关环法合成多氮杂环噻二唑‑5‑甲脒类化合物 |
| HUE051950T2 (hu) | 2015-06-15 | 2021-04-28 | Bayer Cropscience Ag | Halogén-szubsztituált fenoxifenilamidinok és alkalmazásuk fungicidként |
| EP3307706B1 (en) | 2015-06-15 | 2019-07-24 | Bayer CropScience AG | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
| WO2017005710A1 (en) | 2015-07-08 | 2017-01-12 | Bayer Cropscience Aktiengesellschaft | Phenoxyhalogenphenylamidines and the use thereof as fungicides |
| CN107200712A (zh) * | 2016-03-16 | 2017-09-26 | 浙江省化工研究院有限公司 | 一类含取代基嘧啶芳基脒类化合物、其制备方法及应用 |
| CN108059618B (zh) * | 2016-11-08 | 2020-07-07 | 浙江省化工研究院有限公司 | 一类含多氟嘧啶芳基脒类化合物、其制备方法及应用 |
| WO2018109002A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| JP2020502105A (ja) | 2016-12-14 | 2020-01-23 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | フェノキシフェニルアミジンおよびその殺菌剤としての使用 |
| EP3335559A1 (en) | 2016-12-14 | 2018-06-20 | Bayer CropScience Aktiengesellschaft | Active compound combinations |
| WO2018108998A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Phenylamidines and the use thereof as fungicides |
| TWI760428B (zh) | 2017-01-26 | 2022-04-11 | 日商三井化學Agro股份有限公司 | 吡啶酮化合物及以吡啶酮化合物作為有效成分的農園藝用殺菌劑 |
| US11147272B2 (en) | 2017-04-10 | 2021-10-19 | Mitsui Chemicals Argro, Inc. | Pyridone compounds and agricultural and horticultural fungicides comprising the same as active ingredients |
| JP7134946B2 (ja) | 2017-04-10 | 2022-09-12 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
| BR112019021388B1 (pt) | 2017-04-11 | 2023-10-31 | Mitsui Chemicals Crop & Life Solutions, Inc | Compostos, agente de controle de pragas agrícolas e hortícolas, fungicida agrícola e hortícola e métodos para prevenção e/ou tratamento de uma doença de plantas |
| CA3059301A1 (en) | 2017-04-20 | 2018-10-25 | Pi Industries Ltd. | Novel phenylamine compounds |
| WO2018211442A1 (en) | 2017-05-18 | 2018-11-22 | Pi Industries Ltd. | Formimidamidine compounds useful against phytopathogenic microorganisms |
| JP7157738B2 (ja) | 2017-06-08 | 2022-10-20 | 三井化学アグロ株式会社 | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 |
| US10513515B2 (en) | 2017-08-25 | 2019-12-24 | Biotheryx, Inc. | Ether compounds and uses thereof |
| EP3828177B1 (en) | 2018-07-25 | 2023-11-29 | Mitsui Chemicals Crop & Life Solutions, Inc. | Pyridone compound and agricultural and horticultural fungicide having this as active component |
| CA3106239A1 (en) | 2018-07-27 | 2020-01-30 | Biotheryx, Inc. | Bifunctional compounds as cdk modulators |
| EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
| WO2021222150A2 (en) | 2020-04-28 | 2021-11-04 | Anwita Biosciences, Inc. | Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications |
| EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574226A (en) * | 1967-05-19 | 1971-04-06 | Ansul Co | Substituted delta**2-1,2,4-thiadiazolin-5-ones |
| US3692794A (en) * | 1970-09-03 | 1972-09-19 | Ciba Geigy Corp | 1,2,4-thiadiazoles |
| DE2242187A1 (de) | 1971-08-31 | 1973-03-08 | Ciba Geigy Ag | Heterocyclische verbindungen |
| CH550538A (de) * | 1971-08-31 | 1974-06-28 | Ciba Geigy Ag | Handelsfaehiges mittel zur bekaempfung von schaedlichen mikroorganismen. |
| BR9711816A (pt) * | 1996-08-01 | 1999-08-31 | Du Pont | Composto, composição fungicida, método para controlar doenças de plantas causadas pelos agentes patogênicos f·ngicos de plantas, composição artropodicida e método para controlar artrópodes. |
| GB9902592D0 (en) * | 1999-02-06 | 1999-03-24 | Hoechst Schering Agrevo Gmbh | Fungicides |
| FR2829362B1 (fr) | 2001-09-10 | 2003-11-07 | Aventis Cropscience Sa | Composition fongicide a base de derives d'arylamidine et de composes fongicides connus |
| EP1501789A1 (en) | 2002-05-03 | 2005-02-02 | E.I. Du Pont De Nemours And Company | Amidinylphenyl compounds and their use as fungicides |
| EP1413301A1 (fr) | 2002-10-24 | 2004-04-28 | Bayer CropScience SA | Médicaments antifongiques à base de dérivés d'arylamidine |
| CN102766110A (zh) * | 2005-09-13 | 2012-11-07 | 拜尔农科股份公司 | 农药噻唑氧基取代的苯脒衍生物 |
| GB0602335D0 (en) * | 2006-02-07 | 2006-03-15 | Remynd Nv | Thiadiazole Derivatives For The Treatment Of Neurodegenerative Diseases |
| GB0623258D0 (en) | 2006-11-22 | 2007-01-03 | Remynd Nv | Thiadiazole derivatives for the treatment of neuro-degenerative diseases |
| BRPI0913885A8 (pt) * | 2008-06-27 | 2016-08-02 | Bayer Cropscience Ag | tiadiazoliloxifenilamidinas e seu uso como fungicidas |
-
2009
- 2009-06-19 WO PCT/EP2009/004419 patent/WO2009156098A2/de not_active Ceased
- 2009-06-19 AU AU2009262515A patent/AU2009262515A1/en not_active Abandoned
- 2009-06-19 CN CN200980122989.0A patent/CN102066347B/zh not_active Expired - Fee Related
- 2009-06-19 US US13/000,233 patent/US8383139B2/en not_active Expired - Fee Related
- 2009-06-19 PL PL09768947T patent/PL2307391T3/pl unknown
- 2009-06-19 UA UAA201100889A patent/UA104293C2/uk unknown
- 2009-06-19 JP JP2011515173A patent/JP5713352B2/ja not_active Expired - Fee Related
- 2009-06-19 BR BRPI0914536A patent/BRPI0914536A8/pt not_active IP Right Cessation
- 2009-06-19 EP EP09768947.5A patent/EP2307391B1/de not_active Not-in-force
- 2009-06-19 EA EA201100094A patent/EA020256B9/ru not_active IP Right Cessation
- 2009-06-19 CA CA2729432A patent/CA2729432A1/en not_active Abandoned
- 2009-06-26 TW TW098121496A patent/TW201014529A/zh unknown
- 2009-06-26 AR ARP090102377A patent/AR072373A1/es unknown
-
2010
- 2010-12-23 CL CL2010001530A patent/CL2010001530A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2307391A2 (de) | 2011-04-13 |
| EA201100094A1 (ru) | 2011-06-30 |
| JP2011525509A (ja) | 2011-09-22 |
| WO2009156098A2 (de) | 2009-12-30 |
| BRPI0914536A8 (pt) | 2017-05-16 |
| CN102066347A (zh) | 2011-05-18 |
| AR072373A1 (es) | 2010-08-25 |
| CN102066347B (zh) | 2016-06-08 |
| UA104293C2 (en) | 2014-01-27 |
| CL2010001530A1 (es) | 2011-05-06 |
| JP5713352B2 (ja) | 2015-05-07 |
| BRPI0914536A2 (pt) | 2016-07-26 |
| PL2307391T3 (pl) | 2014-06-30 |
| CA2729432A1 (en) | 2009-12-30 |
| WO2009156098A3 (de) | 2010-04-01 |
| US8383139B2 (en) | 2013-02-26 |
| AU2009262515A1 (en) | 2009-12-30 |
| EA020256B1 (ru) | 2014-09-30 |
| EP2307391B1 (de) | 2014-01-01 |
| EA020256B9 (ru) | 2015-02-27 |
| US20110143937A1 (en) | 2011-06-16 |
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