DD247216A5 - Verfahren zur herstellung von 4-(c tief 1-c tief 4-alkyl-suelfonyl)-2-chloro-3-hydroxybenzoesaeure - Google Patents
Verfahren zur herstellung von 4-(c tief 1-c tief 4-alkyl-suelfonyl)-2-chloro-3-hydroxybenzoesaeure Download PDFInfo
- Publication number
- DD247216A5 DD247216A5 DD86287607A DD28760786A DD247216A5 DD 247216 A5 DD247216 A5 DD 247216A5 DD 86287607 A DD86287607 A DD 86287607A DD 28760786 A DD28760786 A DD 28760786A DD 247216 A5 DD247216 A5 DD 247216A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- acid
- carbon atoms
- chloro
- prepared
- alkylthio
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- 230000020477 pH reduction Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 23
- 239000000543 intermediate Substances 0.000 abstract description 18
- -1 2- (2,3,4-trisubstituted benzoyl) -1,3-cyclohexanediones Chemical class 0.000 abstract description 16
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 5
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 235000010233 benzoic acid Nutrition 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- VTMRWQTZIFUPPE-UHFFFAOYSA-N 2,3-dichloro-4-ethylsulfonylbenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(C(O)=O)C(Cl)=C1Cl VTMRWQTZIFUPPE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001559 benzoic acids Chemical class 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VBTOBUQQWPCYGH-UHFFFAOYSA-N 2-chloro-4-ethylsulfonyl-3-hydroxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(C(O)=O)C(Cl)=C1O VBTOBUQQWPCYGH-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- WCNBDSGSOIBMLL-UHFFFAOYSA-N 1,6-dichloro-6-ethylsulfanylcyclohexa-1,3-diene Chemical compound CCSC1(Cl)CC=CC=C1Cl WCNBDSGSOIBMLL-UHFFFAOYSA-N 0.000 description 1
- UTSMGKMOUSGZSR-UHFFFAOYSA-N 2,3-dichloro-4-ethylbenzenecarbothioic s-acid Chemical compound CCC1=CC=C(C(O)=S)C(Cl)=C1Cl UTSMGKMOUSGZSR-UHFFFAOYSA-N 0.000 description 1
- QGRKONUHHGBHRB-UHFFFAOYSA-N 2,3-dichlorobenzenethiol Chemical compound SC1=CC=CC(Cl)=C1Cl QGRKONUHHGBHRB-UHFFFAOYSA-N 0.000 description 1
- MTRWJDMLVHGZEX-UHFFFAOYSA-N 2-chloro-3-ethoxy-4-ethylsulfonylbenzoic acid Chemical compound CCOC1=C(Cl)C(C(O)=O)=CC=C1S(=O)(=O)CC MTRWJDMLVHGZEX-UHFFFAOYSA-N 0.000 description 1
- KYFPVRGSRBQCKG-UHFFFAOYSA-N 2-chloro-3-ethyl-4-ethylsulfonylbenzenecarbothioic s-acid Chemical compound CCC1=C(Cl)C(C(S)=O)=CC=C1S(=O)(=O)CC KYFPVRGSRBQCKG-UHFFFAOYSA-N 0.000 description 1
- IKJJCBZYFSEBSH-UHFFFAOYSA-N 2-chloro-3-ethylsulfanyl-4-ethylsulfonylbenzoic acid Chemical compound CCSC1=C(Cl)C(C(O)=O)=CC=C1S(=O)(=O)CC IKJJCBZYFSEBSH-UHFFFAOYSA-N 0.000 description 1
- CCZWSTFVHJPCEM-UHFFFAOYSA-N 2-iodopyridine Chemical compound IC1=CC=CC=N1 CCZWSTFVHJPCEM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical compound N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/65—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfone or sulfoxide groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Steroid Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/709,006 US4898973A (en) | 1985-03-07 | 1985-03-07 | Trisubstituted benzoic acid intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD247216A5 true DD247216A5 (de) | 1987-07-01 |
Family
ID=24848089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86287607A DD247216A5 (de) | 1985-03-07 | 1986-03-05 | Verfahren zur herstellung von 4-(c tief 1-c tief 4-alkyl-suelfonyl)-2-chloro-3-hydroxybenzoesaeure |
Country Status (31)
| Country | Link |
|---|---|
| US (3) | US4898973A (cs) |
| EP (1) | EP0195247B1 (cs) |
| JP (3) | JPH0660158B2 (cs) |
| KR (1) | KR900003789B1 (cs) |
| CN (1) | CN1009086B (cs) |
| AT (1) | ATE40682T1 (cs) |
| AU (1) | AU585316B2 (cs) |
| BG (1) | BG46455A3 (cs) |
| BR (1) | BR8601007A (cs) |
| CA (1) | CA1266485A1 (cs) |
| CS (1) | CS270431B2 (cs) |
| DD (1) | DD247216A5 (cs) |
| DE (1) | DE3662042D1 (cs) |
| DK (3) | DK171296B1 (cs) |
| ES (1) | ES8800143A1 (cs) |
| FI (1) | FI89908C (cs) |
| GR (1) | GR860609B (cs) |
| HU (1) | HU198905B (cs) |
| IE (1) | IE59252B1 (cs) |
| IL (1) | IL78058A (cs) |
| MY (1) | MY101513A (cs) |
| NO (1) | NO163403C (cs) |
| NZ (1) | NZ215384A (cs) |
| PH (1) | PH22179A (cs) |
| PL (1) | PL148300B1 (cs) |
| PT (1) | PT82136B (cs) |
| RO (1) | RO92753A (cs) |
| SU (1) | SU1436870A3 (cs) |
| YU (1) | YU46000B (cs) |
| ZA (1) | ZA861630B (cs) |
| ZW (1) | ZW5686A1 (cs) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2734579B2 (ja) * | 1988-09-19 | 1998-03-30 | 日産化学工業株式会社 | 置換安息香酸の製造方法 |
| US5075497A (en) * | 1988-11-18 | 1991-12-24 | Ici Americas, Inc. | Trisubstituted benzoic acid intermediates |
| US5073642A (en) * | 1988-11-18 | 1991-12-17 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| US5001256A (en) * | 1988-11-18 | 1991-03-19 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| US5047572A (en) * | 1988-11-18 | 1991-09-10 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| US5068423A (en) * | 1988-11-18 | 1991-11-26 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| WO1990005715A1 (en) * | 1988-11-18 | 1990-05-31 | Ici Americas Inc. | Trisubstituted benzoic acid intermediates |
| GB9310203D0 (en) * | 1993-05-18 | 1993-06-30 | Rhone Poulenc Agriculture | Compositions of new matter |
| US5101065A (en) * | 1991-02-04 | 1992-03-31 | Imperial Chemical Industries Plc | Acetophenone intermediates |
| US5153357A (en) * | 1991-02-04 | 1992-10-06 | Imperical Chemical Industries Plc | Preparation of trisubstituted benzoic acids and intermediates |
| JPH05170730A (ja) * | 1991-12-25 | 1993-07-09 | Nippon Soda Co Ltd | 新規な中間体化合物及びその製法 |
| DE59605056D1 (de) * | 1995-02-24 | 2000-05-31 | Basf Ag | Phenyldiketon-derivate als herbizide |
| CA2213124C (en) * | 1995-02-24 | 2005-04-26 | Basf Aktiengesellschaft | Benzoyl derivatives |
| DK0880498T3 (da) * | 1996-02-01 | 2002-05-21 | Aventis Cropscience Sa | Fremgangsmåde til fremstilling af diketonforbindelser |
| US6211403B1 (en) | 1997-03-24 | 2001-04-03 | Dow Agrosciences Llc | Process for preparing 2-chloro-3-alkoxy-4-alkylsulfonyl-benzoic acids and esters |
| ZA982449B (en) * | 1997-03-24 | 1999-09-23 | Dow Agrosciences Llc | Process for preparing 1-Alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole and related compounds. |
| JP4592129B2 (ja) * | 1998-07-14 | 2010-12-01 | 日本曹達株式会社 | 新規な安息香酸誘導体及びその製造法 |
| DE69933222T2 (de) * | 1998-07-14 | 2007-01-04 | Nippon Soda Co. Ltd. | Benzoesäurederivate und verfahren zu ihrer herstellung |
| AR056889A1 (es) | 2005-12-15 | 2007-10-31 | Ishihara Sangyo Kaisha | Compuestos benzoilpirazol y herbicidas que los contienen |
| CN101691347A (zh) * | 2009-09-28 | 2010-04-07 | 唐保清 | 对三氟甲硫基苯甲酰氯的制备工艺 |
| DE102017010478A1 (de) * | 2016-12-02 | 2018-06-07 | Merck Patent Gmbh | Thioether-Verbindungen |
| CN113387942B (zh) | 2020-03-13 | 2025-08-01 | 沈阳中化农药化工研发有限公司 | 一种吡唑羧酸酯类化合物及其应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3729508A (en) * | 1969-11-20 | 1973-04-24 | Merck & Co Inc | Sulfonylbenzoic acids |
| US3663615A (en) * | 1970-03-02 | 1972-05-16 | Merck & Co Inc | Nuclear sulfamoyl n-organosulfonyl benzamides |
| BE793689A (fr) * | 1972-07-19 | 1973-05-02 | Renfag Sa | Procede de preparation d'acides 2-alcoxy-5-alcoysulfonylbenzoique |
| US4350705A (en) * | 1979-03-31 | 1982-09-21 | Eisai Co., Ltd. | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
| CH657849A5 (en) * | 1980-07-17 | 1986-09-30 | Ciba Geigy Ag | N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinyl ureas |
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| JPS58198464A (ja) * | 1982-05-14 | 1983-11-18 | Seitetsu Kagaku Co Ltd | ４−メチルチオ−２−アルコキシ安息香酸の製法 |
| DE3474297D1 (en) * | 1983-09-16 | 1988-11-03 | Stauffer Chemical Co | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| US4816066A (en) * | 1983-09-16 | 1989-03-28 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| US4681621A (en) * | 1984-12-20 | 1987-07-21 | Stauffer Chemical Company | Herbicidal 2-(2-substituted benzoyl)-1,3-cyclopentanediones |
| US4806146A (en) * | 1984-12-20 | 1989-02-21 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| US4695673A (en) * | 1985-11-20 | 1987-09-22 | Stauffer Chemical Company | Process for the production of acylated 1,3-dicarbonyl compounds |
-
1985
- 1985-03-07 US US06/709,006 patent/US4898973A/en not_active Expired - Lifetime
-
1986
- 1986-02-14 EP EP86101898A patent/EP0195247B1/en not_active Expired
- 1986-02-14 AT AT86101898T patent/ATE40682T1/de not_active IP Right Cessation
- 1986-02-14 DE DE8686101898T patent/DE3662042D1/de not_active Expired
- 1986-02-27 KR KR1019860001369A patent/KR900003789B1/ko not_active Expired
- 1986-03-03 CN CN86101277A patent/CN1009086B/zh not_active Expired
- 1986-03-04 FI FI860900A patent/FI89908C/fi not_active IP Right Cessation
- 1986-03-04 PH PH33475A patent/PH22179A/en unknown
- 1986-03-04 PT PT82136A patent/PT82136B/pt not_active IP Right Cessation
- 1986-03-05 GR GR860609A patent/GR860609B/el unknown
- 1986-03-05 ZA ZA861630A patent/ZA861630B/xx unknown
- 1986-03-05 DD DD86287607A patent/DD247216A5/de not_active IP Right Cessation
- 1986-03-05 RO RO86122453A patent/RO92753A/ro unknown
- 1986-03-06 CS CS861564A patent/CS270431B2/cs not_active IP Right Cessation
- 1986-03-06 YU YU33286A patent/YU46000B/sh unknown
- 1986-03-06 IE IE59186A patent/IE59252B1/en not_active IP Right Cessation
- 1986-03-06 AU AU54363/86A patent/AU585316B2/en not_active Ceased
- 1986-03-06 ZW ZW56/86A patent/ZW5686A1/xx unknown
- 1986-03-06 CA CA000503424A patent/CA1266485A1/en active Granted
- 1986-03-06 IL IL78058A patent/IL78058A/xx unknown
- 1986-03-06 HU HU86969A patent/HU198905B/hu not_active IP Right Cessation
- 1986-03-06 NZ NZ215384A patent/NZ215384A/xx unknown
- 1986-03-06 SU SU864027161A patent/SU1436870A3/ru active
- 1986-03-06 NO NO860850A patent/NO163403C/no not_active IP Right Cessation
- 1986-03-06 JP JP61047467A patent/JPH0660158B2/ja not_active Expired - Lifetime
- 1986-03-07 ES ES552804A patent/ES8800143A1/es not_active Expired
- 1986-03-07 BG BG073980A patent/BG46455A3/xx unknown
- 1986-03-07 BR BR8601007A patent/BR8601007A/pt not_active IP Right Cessation
- 1986-03-07 DK DK106186A patent/DK171296B1/da not_active IP Right Cessation
- 1986-03-07 PL PL1986258287A patent/PL148300B1/pl unknown
-
1987
- 1987-09-18 MY MYPI87001765A patent/MY101513A/en unknown
-
1989
- 1989-12-07 US US07/447,360 patent/US4966998A/en not_active Expired - Lifetime
- 1989-12-07 US US07/447,359 patent/US5097068A/en not_active Expired - Fee Related
-
1990
- 1990-09-03 DK DK199002108A patent/DK173261B1/da not_active IP Right Cessation
- 1990-09-03 DK DK199002107A patent/DK173258B1/da not_active IP Right Cessation
-
1993
- 1993-11-30 JP JP5300687A patent/JPH0688964B2/ja not_active Expired - Lifetime
- 1993-11-30 JP JP5300688A patent/JPH0748342A/ja active Pending
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