ZA200601145B - Production process of optically poure 2-(4-hydroxyphenoxy)-propionic acid compounds - Google Patents
Production process of optically poure 2-(4-hydroxyphenoxy)-propionic acid compounds Download PDFInfo
- Publication number
- ZA200601145B ZA200601145B ZA200601145A ZA200601145A ZA200601145B ZA 200601145 B ZA200601145 B ZA 200601145B ZA 200601145 A ZA200601145 A ZA 200601145A ZA 200601145 A ZA200601145 A ZA 200601145A ZA 200601145 B ZA200601145 B ZA 200601145B
- Authority
- ZA
- South Africa
- Prior art keywords
- acid
- hydroxyphenoxy
- salt
- reducing agent
- butyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- AQIHDXGKQHFBNW-UHFFFAOYSA-N 2-(4-hydroxyphenoxy)propanoic acid Chemical class OC(=O)C(C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-UHFFFAOYSA-N 0.000 title 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 40
- 239000002253 acid Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- AQIHDXGKQHFBNW-ZCFIWIBFSA-N (2r)-2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-ZCFIWIBFSA-N 0.000 claims description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- 239000005498 Clodinafop Substances 0.000 claims description 6
- 239000005502 Cyhalofop-butyl Substances 0.000 claims description 6
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims description 6
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 claims description 6
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 claims description 6
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- 239000005614 Quizalofop-P-ethyl Substances 0.000 claims description 5
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 claims description 5
- MFSWTRQUCLNFOM-SECBINFHSA-N haloxyfop-P-methyl Chemical group C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-SECBINFHSA-N 0.000 claims description 5
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- 125000003106 haloaryl group Chemical group 0.000 claims description 3
- 125000005216 haloheteroaryl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 229960005070 ascorbic acid Drugs 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- 235000010269 sulphur dioxide Nutrition 0.000 claims 1
- 239000004291 sulphur dioxide Substances 0.000 claims 1
- 229960004337 hydroquinone Drugs 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 7
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229960005419 nitrogen Drugs 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 1
- MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 239000004285 Potassium sulphite Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- RHWBAORFZYOJII-FYZOBXCZSA-M potassium;(2r)-2-(4-hydroxyphenoxy)propanoate Chemical compound [K+].[O-]C(=O)[C@@H](C)OC1=CC=C(O)C=C1 RHWBAORFZYOJII-FYZOBXCZSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- YCCOIVJFDCWMFT-UHFFFAOYSA-J tetrapotassium;disulfite Chemical compound [K+].[K+].[K+].[K+].[O-]S([O-])=O.[O-]S([O-])=O YCCOIVJFDCWMFT-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0322917.6A GB0322917D0 (en) | 2003-09-30 | 2003-09-30 | Chemical process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200601145B true ZA200601145B (en) | 2007-05-30 |
Family
ID=29415251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200601145A ZA200601145B (en) | 2003-09-30 | 2006-02-08 | Production process of optically poure 2-(4-hydroxyphenoxy)-propionic acid compounds |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7268249B2 (zh) |
| EP (1) | EP1670743B1 (zh) |
| JP (2) | JP4965256B2 (zh) |
| KR (1) | KR101102822B1 (zh) |
| CN (1) | CN100422129C (zh) |
| AT (1) | ATE353868T1 (zh) |
| BR (1) | BRPI0414925B1 (zh) |
| CA (1) | CA2535039C (zh) |
| DE (1) | DE602004004810T2 (zh) |
| DK (1) | DK1670743T3 (zh) |
| EA (1) | EA009241B1 (zh) |
| ES (1) | ES2282897T3 (zh) |
| GB (1) | GB0322917D0 (zh) |
| IL (1) | IL173524A (zh) |
| PL (1) | PL1670743T3 (zh) |
| PT (1) | PT1670743E (zh) |
| TW (1) | TWI343911B (zh) |
| WO (1) | WO2005042460A1 (zh) |
| ZA (1) | ZA200601145B (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100467452C (zh) * | 2006-11-01 | 2009-03-11 | 浙江工业大学 | 一种制备具有高光学纯度精吡氟氯禾灵的方法 |
| CN101835742A (zh) * | 2007-10-24 | 2010-09-15 | 陶氏益农公司 | 制备r-(+)-2-(4-(4-氰基-2-氟苯氧基)苯氧基)丙酸酯类的改进方法 |
| CN102391104A (zh) * | 2011-09-16 | 2012-03-28 | 南通嘉禾化工有限公司 | 一种（r）-（+）-2-对羟基苯氧基丙酸的合成及其分离工艺 |
| CN102584691A (zh) * | 2012-01-12 | 2012-07-18 | 南京红太阳生物化学有限责任公司 | 一种合成炔草酯的新方法 |
| DE102016221270B4 (de) * | 2015-11-30 | 2019-03-21 | Ford Global Technologies, Llc | Mobile Transportvorrichtung, Fahrzeug und Verfahren zum Bewegen einer mobilen Transportvorrichtung |
| CN111187155B (zh) * | 2020-03-25 | 2022-04-05 | 江苏三吉利化工股份有限公司 | 一种气相催化合成r-(+)-2-(4-羟基苯氧基)丙酸的方法 |
| JP7695149B2 (ja) * | 2021-08-17 | 2025-06-18 | 住友化学株式会社 | エーテル化合物の製造方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR763374A (fr) * | 1933-01-23 | 1934-04-30 | Manuf De Prod Chim Purs | Procédé pour la préparation des antipodes optiques de corps doués de pouvoir rotatoire |
| JPS5616475A (en) * | 1979-07-19 | 1981-02-17 | Nissan Chem Ind Ltd | Quinoxaline derivative and herbicide containing the same as effective component |
| US4505743A (en) * | 1981-12-31 | 1985-03-19 | Ciba-Geigy Corporation | α-[4-(3-Fluoro-5'-halopyridyl-2'-oxy)-phenoxy]-propionic acid derivatives having herbicidal activity |
| DE3240805A1 (de) * | 1982-11-05 | 1984-05-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von hydroxy-phenoxy-alkancarbonsaeuren |
| US4505753A (en) * | 1983-06-30 | 1985-03-19 | Research One Limited Partnership | Cementitious composite material |
| JPS60123443A (ja) * | 1983-12-07 | 1985-07-02 | Nissan Chem Ind Ltd | ２−（４−ヒドロキシフェノキシ）アルカン酸の製造方法 |
| JPH0610154B2 (ja) * | 1984-12-28 | 1994-02-09 | 日産化学工業株式会社 | 光学活性２−（４−ヒドロキシフエノキシ）プロピオン酸の製法 |
| FR2634481B1 (fr) * | 1988-07-20 | 1990-09-14 | Rhone Poulenc Chimie | Procede de purification de l'acide d-hydroxyphenoxypropionique |
| JP2514072B2 (ja) * | 1988-07-20 | 1996-07-10 | ダイセル化学工業株式会社 | 光学活性２−（４−ヒドロキシフェノキシ）プロピオン酸の製法 |
| JPH02268134A (ja) * | 1989-04-11 | 1990-11-01 | Tosoh Corp | 光学活性２―（４―ヒドロキシフェノキシ）プロピオン酸の製造法 |
| JPH08134018A (ja) * | 1994-11-04 | 1996-05-28 | Nippon Green Consultant Kk | ３−（２−ヒドロキシフェノキシ）プロピオン酸誘導体の製造方法 |
-
2003
- 2003-09-30 GB GBGB0322917.6A patent/GB0322917D0/en not_active Ceased
-
2004
- 2004-08-16 PL PL04768060T patent/PL1670743T3/pl unknown
- 2004-08-16 ES ES04768060T patent/ES2282897T3/es not_active Expired - Lifetime
- 2004-08-16 EP EP04768060A patent/EP1670743B1/en not_active Expired - Lifetime
- 2004-08-16 DK DK04768060T patent/DK1670743T3/da active
- 2004-08-16 BR BRPI0414925-4A patent/BRPI0414925B1/pt not_active IP Right Cessation
- 2004-08-16 WO PCT/GB2004/003497 patent/WO2005042460A1/en not_active Ceased
- 2004-08-16 PT PT04768060T patent/PT1670743E/pt unknown
- 2004-08-16 CN CNB2004800267093A patent/CN100422129C/zh not_active Expired - Lifetime
- 2004-08-16 US US10/571,863 patent/US7268249B2/en not_active Expired - Lifetime
- 2004-08-16 JP JP2006530547A patent/JP4965256B2/ja not_active Expired - Lifetime
- 2004-08-16 CA CA2535039A patent/CA2535039C/en not_active Expired - Lifetime
- 2004-08-16 KR KR1020067006076A patent/KR101102822B1/ko not_active Expired - Lifetime
- 2004-08-16 EA EA200600496A patent/EA009241B1/ru not_active IP Right Cessation
- 2004-08-16 DE DE602004004810T patent/DE602004004810T2/de not_active Expired - Lifetime
- 2004-08-16 AT AT04768060T patent/ATE353868T1/de active
- 2004-08-30 TW TW093126006A patent/TWI343911B/zh not_active IP Right Cessation
-
2006
- 2006-02-02 IL IL173524A patent/IL173524A/en active IP Right Grant
- 2006-02-08 ZA ZA200601145A patent/ZA200601145B/en unknown
-
2011
- 2011-08-01 JP JP2011168718A patent/JP2011236244A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL173524A0 (en) | 2006-07-05 |
| PT1670743E (pt) | 2007-03-30 |
| EA200600496A1 (ru) | 2006-10-27 |
| TW200512185A (en) | 2005-04-01 |
| PL1670743T3 (pl) | 2007-06-29 |
| BRPI0414925A (pt) | 2006-11-07 |
| TWI343911B (en) | 2011-06-21 |
| JP2007507478A (ja) | 2007-03-29 |
| KR20060094954A (ko) | 2006-08-30 |
| GB0322917D0 (en) | 2003-11-05 |
| IL173524A (en) | 2010-11-30 |
| EA009241B1 (ru) | 2007-12-28 |
| JP4965256B2 (ja) | 2012-07-04 |
| ATE353868T1 (de) | 2007-03-15 |
| CA2535039C (en) | 2012-06-26 |
| BRPI0414925B1 (pt) | 2014-02-18 |
| JP2011236244A (ja) | 2011-11-24 |
| CA2535039A1 (en) | 2005-05-12 |
| CN100422129C (zh) | 2008-10-01 |
| DE602004004810D1 (de) | 2007-03-29 |
| KR101102822B1 (ko) | 2012-01-05 |
| DE602004004810T2 (de) | 2007-12-06 |
| DK1670743T3 (da) | 2007-05-29 |
| ES2282897T3 (es) | 2007-10-16 |
| EP1670743B1 (en) | 2007-02-14 |
| US7268249B2 (en) | 2007-09-11 |
| WO2005042460A1 (en) | 2005-05-12 |
| EP1670743A1 (en) | 2006-06-21 |
| US20060270851A1 (en) | 2006-11-30 |
| CN1852884A (zh) | 2006-10-25 |
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