ES2525535T3 - Procedimiento para la preparación de derivados de 3-triazolil-sulfóxido quirales - Google Patents
Procedimiento para la preparación de derivados de 3-triazolil-sulfóxido quirales Download PDFInfo
- Publication number
- ES2525535T3 ES2525535T3 ES10732316.4T ES10732316T ES2525535T3 ES 2525535 T3 ES2525535 T3 ES 2525535T3 ES 10732316 T ES10732316 T ES 10732316T ES 2525535 T3 ES2525535 T3 ES 2525535T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- chiral
- hydrogen
- independently represent
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000000034 method Methods 0.000 title abstract description 19
- YZXYLAXJHXMUPM-UHFFFAOYSA-N 1-(triazol-1-ylsulfinyl)triazole Chemical class C1=CN=NN1S(=O)N1C=CN=N1 YZXYLAXJHXMUPM-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title abstract description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 17
- -1 alkyl hydroperoxide Chemical compound 0.000 abstract description 11
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 5
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229910052723 transition metal Inorganic materials 0.000 abstract 1
- 150000003624 transition metals Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003608 titanium Chemical class 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- FSJSYDFBTIVUFD-XHTSQIMGSA-N (e)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O FSJSYDFBTIVUFD-XHTSQIMGSA-N 0.000 description 1
- ZGPNSMMDSNHBOH-UHFFFAOYSA-N 1-(trifluoromethyl)-1,2,4-triazole Chemical compound FC(F)(F)N1C=NC=N1 ZGPNSMMDSNHBOH-UHFFFAOYSA-N 0.000 description 1
- FDMINIQYGOXHLX-UHFFFAOYSA-N 1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-3-(trifluoromethyl)-1,2,4-triazole Chemical compound C1=C(SCC(F)(F)F)C(C)=CC(C)=C1N1N=C(C(F)(F)F)N=C1 FDMINIQYGOXHLX-UHFFFAOYSA-N 0.000 description 1
- AXJXMJMPSIZOSF-UHFFFAOYSA-N 1-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-3-(trifluoromethyl)-1,2,4-triazole Chemical compound CC1=CC(C)=C(S(=O)CC(F)(F)F)C=C1N1N=C(C(F)(F)F)N=C1 AXJXMJMPSIZOSF-UHFFFAOYSA-N 0.000 description 1
- QBLAJFNGSINFEB-WSDLNYQXSA-N CC(C)(C)C(CO)\N=C\C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O Chemical compound CC(C)(C)C(CO)\N=C\C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O QBLAJFNGSINFEB-WSDLNYQXSA-N 0.000 description 1
- YSAVZVORKRDODB-UHFFFAOYSA-N Diethyl tartrate Chemical compound CCOC(=O)C(O)C(O)C(=O)OCC YSAVZVORKRDODB-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UAWABSHMGXMCRK-UHFFFAOYSA-L Kagan reagent Substances I[Sm]I UAWABSHMGXMCRK-UHFFFAOYSA-L 0.000 description 1
- 102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
- 108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 108700020962 Peroxidase Proteins 0.000 description 1
- 102000003992 Peroxidases Human genes 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 238000006202 Sharpless epoxidation reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VHILIAIEEYLJNA-UHFFFAOYSA-N methyl p-tolyl sulfide Chemical compound CSC1=CC=C(C)C=C1 VHILIAIEEYLJNA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009027771 | 2009-07-16 | ||
| DE102009027771 | 2009-07-16 | ||
| PCT/EP2010/004288 WO2011006646A1 (de) | 2009-07-16 | 2010-07-14 | Verfahren zur herstellung von chiralen 3-triazolyl-sulfoxid-derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2525535T3 true ES2525535T3 (es) | 2014-12-26 |
Family
ID=42710633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10732316.4T Active ES2525535T3 (es) | 2009-07-16 | 2010-07-14 | Procedimiento para la preparación de derivados de 3-triazolil-sulfóxido quirales |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US8314133B2 (enExample) |
| EP (1) | EP2454242B1 (enExample) |
| JP (1) | JP5676602B2 (enExample) |
| KR (1) | KR20120037993A (enExample) |
| CN (1) | CN102471290B (enExample) |
| BR (1) | BR112012001078A8 (enExample) |
| DK (1) | DK2454242T3 (enExample) |
| ES (1) | ES2525535T3 (enExample) |
| IL (1) | IL217136A0 (enExample) |
| IN (1) | IN2012DN00422A (enExample) |
| MX (1) | MX2012000583A (enExample) |
| RU (1) | RU2012105122A (enExample) |
| TW (1) | TWI471314B (enExample) |
| WO (1) | WO2011006646A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2274982A1 (de) * | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| CN102471290B (zh) | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
| RU2012106074A (ru) * | 2009-07-23 | 2013-08-27 | Байер Кропсайенс Аг | Новые алкоксиеноны и енаминокетоны и способ их получения |
| US8242313B2 (en) | 2009-07-23 | 2012-08-14 | Bayer Cropscience Ag | Alkoxy enones and enamino ketones and a process for preparation thereof |
| IN2012DN01531A (enExample) * | 2009-08-20 | 2015-06-05 | Bayer Cropscience Ag | |
| MX2012001969A (es) * | 2009-08-20 | 2012-03-29 | Bayer Cropscience Ag | Derivados de 3-[1-(3-haloalquil)-triazolil]-fenil-sulfuro como acaricidas e insecticidas. |
| US8729116B2 (en) * | 2010-06-01 | 2014-05-20 | Kumiai Chemical Industry Co., Ltd. | Triazole compound having pesticidal activities |
| EP2606726A1 (de) | 2011-12-21 | 2013-06-26 | Bayer CropScience AG | N-Arylamidine-substituierte trifluoroethylsulfid-Derivate als Akarizide und Insektizide |
| ES2625547T3 (es) | 2012-09-27 | 2017-07-19 | Bayer Cropscience Ag | Procedimiento de preparación de fenil y piridil pirrolidinas opcionalmente sustituidas |
| WO2014090765A1 (en) | 2012-12-12 | 2014-06-19 | Bayer Cropscience Ag | Use of 1-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-5-amino-3-trifluoromethyl)-1 h-1,2,4 tfia zole for controlling nematodes in nematode-resistant crops |
| WO2015036380A1 (de) | 2013-09-13 | 2015-03-19 | Bayer Cropscience Ag | Verfahren zur reduktion von arylsulfoxiden zu arylthioethern |
| WO2015135984A1 (de) | 2014-03-13 | 2015-09-17 | Bayer Cropscience Ag | Verfahren zur herstellung von chiralen 3-(5-aminotriazolyl)-sulfoxid-derivaten |
| BR112020007543B1 (pt) * | 2017-10-18 | 2022-06-21 | Bayer Aktiengesellschaft | Combinações de composto ativo sinérgicas, que apresentam propriedades inseticidas/acaricidas, seus usos, método para controlar pragas animais ou microbianas, e processo para preparar um agente de proteção de cultura |
| WO2021084074A1 (en) | 2019-10-30 | 2021-05-06 | Solvay Sa | Compositions and films comprising a polymer and tis2 particles, and their preparation and uses |
| US20230125434A1 (en) | 2020-04-30 | 2023-04-27 | Kumiai Chemical Industry Co., Ltd. | Method for producing monosulfoxide derivative |
| BR112023017032A2 (pt) | 2021-03-26 | 2023-11-14 | Bayer Ag | Processo para preparar derivados de sulfóxido de (2z)-2-(fenilimino)-1,3-tiazolidin-4-ona enantiomericamente enriquecidos |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69934224T2 (de) | 1998-04-27 | 2007-10-04 | Kumiai Chemical Industry Co., Ltd. | 3-arylphenylsulfid-derivate und insektizide und mitizide |
| FR2852956B1 (fr) * | 2003-03-28 | 2006-08-04 | Negma Gild | Procede de preparation enantioselective de derives de sulfoxydes |
| FR2863611B1 (fr) * | 2003-12-15 | 2006-03-24 | Sidem Pharma Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| WO2004087702A2 (fr) | 2003-03-28 | 2004-10-14 | Sidem Pharma | Procede de preparation enantioselective de derives de sulfoxydes. |
| EP1516869A1 (en) * | 2003-09-19 | 2005-03-23 | Cephalon France | Process for enantioselective synthesis of single enantiomers of modafinil by asymmetric oxidation |
| FR2876101B1 (fr) * | 2004-10-05 | 2007-03-02 | Sidem Pharma Sa Sa | Procede de preparation enantioselective de derives de sulfoxydes |
| SI1802584T1 (sl) * | 2004-10-11 | 2010-01-29 | Ranbaxy Lab Ltd | Postopki za pripravo substituiranih sulfoksidov |
| WO2006043635A1 (ja) * | 2004-10-20 | 2006-04-27 | Kumiai Chemical Industry Co., Ltd. | ３－トリアゾリルフェニルスルフィド誘導体及びそれを有効成分として含有する殺虫・殺ダニ・殺線虫剤 |
| CN101012141B (zh) * | 2007-02-02 | 2012-05-23 | 沈阳药科大学 | 手性亚砜类化合物的制备方法 |
| KR101574655B1 (ko) * | 2007-11-30 | 2015-12-04 | 이하라케미칼 고교가부시키가이샤 | (1ｈ-1,2,4-트리아졸-1-일)아릴 화합물 및 그 제조방법 |
| CN101323582A (zh) * | 2008-07-30 | 2008-12-17 | 大连理工大学 | 一类手性西佛碱配体及其在硫醚不对称氧化反应中的应用 |
| CN101429192A (zh) * | 2008-08-22 | 2009-05-13 | 扬子江药业集团有限公司 | 生产手性亚砜衍生物的新方法 |
| CN102471290B (zh) | 2009-07-16 | 2016-02-03 | 拜耳知识产权有限责任公司 | 手性3-三唑基亚砜衍生物的制备方法 |
| EP2274982A1 (de) | 2009-07-16 | 2011-01-19 | Bayer CropScience AG | Verwendung von Phenyltriazolen zur Bekämpfung von Insekten und Spinnmilben durch Angiessen, Tröpfchen- oder Tauchapplikation oder durch Behandlung von Saatgut |
| IN2012DN01531A (enExample) * | 2009-08-20 | 2015-06-05 | Bayer Cropscience Ag | |
| MX2012001969A (es) * | 2009-08-20 | 2012-03-29 | Bayer Cropscience Ag | Derivados de 3-[1-(3-haloalquil)-triazolil]-fenil-sulfuro como acaricidas e insecticidas. |
-
2010
- 2010-07-14 CN CN201080031476.1A patent/CN102471290B/zh not_active Expired - Fee Related
- 2010-07-14 ES ES10732316.4T patent/ES2525535T3/es active Active
- 2010-07-14 BR BR112012001078A patent/BR112012001078A8/pt active Search and Examination
- 2010-07-14 EP EP10732316.4A patent/EP2454242B1/de not_active Not-in-force
- 2010-07-14 DK DK10732316.4T patent/DK2454242T3/en active
- 2010-07-14 RU RU2012105122/04A patent/RU2012105122A/ru not_active Application Discontinuation
- 2010-07-14 KR KR1020127003961A patent/KR20120037993A/ko not_active Withdrawn
- 2010-07-14 WO PCT/EP2010/004288 patent/WO2011006646A1/de not_active Ceased
- 2010-07-14 JP JP2012519925A patent/JP5676602B2/ja not_active Expired - Fee Related
- 2010-07-14 IN IN422DEN2012 patent/IN2012DN00422A/en unknown
- 2010-07-14 MX MX2012000583A patent/MX2012000583A/es active IP Right Grant
- 2010-07-15 TW TW99123228A patent/TWI471314B/zh not_active IP Right Cessation
- 2010-07-16 US US12/837,646 patent/US8314133B2/en not_active Expired - Fee Related
-
2011
- 2011-12-22 IL IL217136A patent/IL217136A0/en unknown
-
2012
- 2012-10-15 US US13/652,039 patent/US8765970B2/en not_active Expired - Fee Related
-
2014
- 2014-05-15 US US14/278,132 patent/US20140256953A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| TW201116517A (en) | 2011-05-16 |
| DK2454242T3 (en) | 2015-02-02 |
| RU2012105122A (ru) | 2013-08-27 |
| US20130172573A1 (en) | 2013-07-04 |
| MX2012000583A (es) | 2012-02-13 |
| US8765970B2 (en) | 2014-07-01 |
| EP2454242B1 (de) | 2014-10-15 |
| BR112012001078A2 (pt) | 2015-09-01 |
| BR112012001078A8 (pt) | 2016-05-03 |
| WO2011006646A1 (de) | 2011-01-20 |
| KR20120037993A (ko) | 2012-04-20 |
| US20110015405A1 (en) | 2011-01-20 |
| JP2012532906A (ja) | 2012-12-20 |
| IL217136A0 (en) | 2012-02-29 |
| EP2454242A1 (de) | 2012-05-23 |
| CN102471290A (zh) | 2012-05-23 |
| IN2012DN00422A (enExample) | 2015-05-15 |
| JP5676602B2 (ja) | 2015-02-25 |
| CN102471290B (zh) | 2016-02-03 |
| US20140256953A1 (en) | 2014-09-11 |
| US8314133B2 (en) | 2012-11-20 |
| TWI471314B (zh) | 2015-02-01 |
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