DE2537973A1 - Verfahren zur herstellung von 3-hydroxy-1,2,4-triazolderivaten - Google Patents
Verfahren zur herstellung von 3-hydroxy-1,2,4-triazolderivatenInfo
- Publication number
- DE2537973A1 DE2537973A1 DE19752537973 DE2537973A DE2537973A1 DE 2537973 A1 DE2537973 A1 DE 2537973A1 DE 19752537973 DE19752537973 DE 19752537973 DE 2537973 A DE2537973 A DE 2537973A DE 2537973 A1 DE2537973 A1 DE 2537973A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- carried out
- group
- formula
- reaction
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 3
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical class OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 title description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 11
- 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 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- -1 2-substituted 2-cyanohydrazine carboxylic acid Chemical class 0.000 claims description 7
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 claims description 7
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical class N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PVZDOUYIWSZEAW-UHFFFAOYSA-N ethyl n-[cyano(propan-2-yl)amino]carbamate Chemical compound CCOC(=O)NN(C#N)C(C)C PVZDOUYIWSZEAW-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- NTXLVYSQEUYSFS-UHFFFAOYSA-N ethyl n-[cyano(cyclopentyl)amino]carbamate Chemical compound CCOC(=O)NN(C#N)C1CCCC1 NTXLVYSQEUYSFS-UHFFFAOYSA-N 0.000 description 2
- CWUWXTPGCLRBFM-UHFFFAOYSA-N ethyl n-[cyano(ethyl)amino]carbamate Chemical compound CCOC(=O)NN(CC)C#N CWUWXTPGCLRBFM-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GKQXPTHQTXCXEV-UHFFFAOYSA-N (4-chlorophenyl)methanethiol Chemical compound SCC1=CC=C(Cl)C=C1 GKQXPTHQTXCXEV-UHFFFAOYSA-N 0.000 description 1
- AWILDOLKOXSYEO-UHFFFAOYSA-N (cyanoamino)carbamic acid Chemical compound OC(=O)NNC#N AWILDOLKOXSYEO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- NZIPKQXAHSBVPS-UHFFFAOYSA-N 2-ethyl-3-methylsulfanyl-1h-1,2,4-triazol-5-one Chemical compound CCN1N=C(O)N=C1SC NZIPKQXAHSBVPS-UHFFFAOYSA-N 0.000 description 1
- LSZXNFXGPVZKPV-UHFFFAOYSA-N 2-methyl-3-methylsulfanyl-1h-1,2,4-triazol-5-one Chemical compound CSC1=NC(O)=NN1C LSZXNFXGPVZKPV-UHFFFAOYSA-N 0.000 description 1
- DAHYWNDNHOAFLE-UHFFFAOYSA-N 3-(dimethylamino)-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1NC(=O)N=C1N(C)C DAHYWNDNHOAFLE-UHFFFAOYSA-N 0.000 description 1
- BYYZSZKHGQDSJF-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylsulfanyl]-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CC(C)N1N=C(O)N=C1SCC1=CC=C(Cl)C=C1 BYYZSZKHGQDSJF-UHFFFAOYSA-N 0.000 description 1
- OFRNLKJZLIGKBN-UHFFFAOYSA-N 3-ethoxy-2-ethyl-1h-1,2,4-triazol-5-one Chemical compound CCOC1=NC(O)=NN1CC OFRNLKJZLIGKBN-UHFFFAOYSA-N 0.000 description 1
- GPLIEVZOSLZRMR-UHFFFAOYSA-N 3-methylsulfanyl-2-propan-2-yl-1h-1,2,4-triazol-5-one Chemical compound CSC1=NC(O)=NN1C(C)C GPLIEVZOSLZRMR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYJQUDWIYRCKHP-UHFFFAOYSA-N CCN(C(=O)O)N(C#N)C(C)C Chemical compound CCN(C(=O)O)N(C#N)C(C)C RYJQUDWIYRCKHP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KWSBBPRKGSJZJO-UHFFFAOYSA-N ethyl n-(cyclopentylamino)carbamate Chemical compound CCOC(=O)NNC1CCCC1 KWSBBPRKGSJZJO-UHFFFAOYSA-N 0.000 description 1
- CWYKSVVUHGYPDF-UHFFFAOYSA-N ethyl n-(ethylamino)carbamate Chemical compound CCNNC(=O)OCC CWYKSVVUHGYPDF-UHFFFAOYSA-N 0.000 description 1
- GLEPDFWPHDUTMJ-UHFFFAOYSA-N ethyl n-(propan-2-ylamino)carbamate Chemical compound CCOC(=O)NNC(C)C GLEPDFWPHDUTMJ-UHFFFAOYSA-N 0.000 description 1
- PHFSVEDDEVZFHJ-UHFFFAOYSA-N ethyl n-[cyano(methyl)amino]carbamate Chemical compound CCOC(=O)NN(C)C#N PHFSVEDDEVZFHJ-UHFFFAOYSA-N 0.000 description 1
- NMRPHPNLPKUGNV-UHFFFAOYSA-N ethyl n-amino-n-ethylcarbamate Chemical compound CCOC(=O)N(N)CC NMRPHPNLPKUGNV-UHFFFAOYSA-N 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
- 210000003608 fece Anatomy 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VGXZECGDNVDUKU-UHFFFAOYSA-N methyl n-(methylamino)carbamate Chemical compound CNNC(=O)OC VGXZECGDNVDUKU-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide group Chemical group NNC(=O)N DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1177174A CH601266A5 (en, 2012) | 1974-08-29 | 1974-08-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2537973A1 true DE2537973A1 (de) | 1976-03-11 |
| DE2537973C2 DE2537973C2 (en, 2012) | 1989-04-06 |
Family
ID=4376715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752537973 Granted DE2537973A1 (de) | 1974-08-29 | 1975-08-26 | Verfahren zur herstellung von 3-hydroxy-1,2,4-triazolderivaten |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5910351B2 (en, 2012) |
| AT (1) | AT342587B (en, 2012) |
| AU (1) | AU499371B2 (en, 2012) |
| BE (1) | BE832830A (en, 2012) |
| CA (1) | CA1070696A (en, 2012) |
| CH (1) | CH601266A5 (en, 2012) |
| CS (1) | CS193522B2 (en, 2012) |
| DD (1) | DD122535A5 (en, 2012) |
| DE (1) | DE2537973A1 (en, 2012) |
| ES (1) | ES440532A1 (en, 2012) |
| FR (1) | FR2283132A1 (en, 2012) |
| GB (1) | GB1512456A (en, 2012) |
| HU (1) | HU172771B (en, 2012) |
| IL (1) | IL48008A (en, 2012) |
| NL (1) | NL7510012A (en, 2012) |
| NZ (1) | NZ178271A (en, 2012) |
| SU (1) | SU577989A3 (en, 2012) |
| ZA (1) | ZA755512B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0062853A3 (en) * | 1981-04-09 | 1983-08-17 | Hoechst Aktiengesellschaft | Process for the preparation of substituted 3-hydroxy-1,2,4-triazoles |
| EP0431390A1 (de) * | 1989-12-02 | 1991-06-12 | Bayer Ag | Substituierte Triazolinone |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3070073D1 (en) * | 1979-10-22 | 1985-03-14 | Glaxo Group Ltd | 1,2,4-triazole derivatives, processes for their production and pharmaceutical compositions containing them |
| GB2064515B (en) * | 1979-10-23 | 1983-06-29 | Glaxo Group Ltd | Heterocyclic derivatives processes for their production and pharmaceutical compositions containing them |
| MY113324A (en) * | 1994-11-21 | 2002-01-31 | Bayer Ip Gmbh | Triazolyl derivatives |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2259974A1 (de) * | 1971-12-10 | 1973-06-14 | Ciba Geigy Ag | Neue ester |
| DE2259960A1 (de) * | 1971-12-10 | 1973-06-14 | Ciba Geigy Ag | Neue ester |
| DE2330089A1 (de) * | 1972-06-16 | 1974-01-03 | Ciba Geigy Ag | Neue ester |
| DE2250572A1 (de) * | 1972-10-14 | 1974-04-18 | Bayer Ag | N,n-dimethyl-o-triazolyl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2360687A1 (de) * | 1972-12-08 | 1974-06-12 | Ciba Geigy Ag | 1,2,4-triazolylphosphorsaeure- bzw. phosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung |
| DE2301400A1 (de) * | 1973-01-12 | 1974-07-18 | Bayer Ag | 0-triazolylthionophosphor(phosphon)saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
-
1974
- 1974-08-29 CH CH1177174A patent/CH601266A5/xx not_active IP Right Cessation
-
1975
- 1975-07-31 NZ NZ178271A patent/NZ178271A/xx unknown
- 1975-08-15 CS CS755621A patent/CS193522B2/cs unknown
- 1975-08-18 SU SU7502163216A patent/SU577989A3/ru active
- 1975-08-25 NL NL7510012A patent/NL7510012A/xx not_active Application Discontinuation
- 1975-08-26 DE DE19752537973 patent/DE2537973A1/de active Granted
- 1975-08-27 HU HU75CI00001600A patent/HU172771B/hu unknown
- 1975-08-27 CA CA234,232A patent/CA1070696A/en not_active Expired
- 1975-08-27 GB GB35411/75A patent/GB1512456A/en not_active Expired
- 1975-08-27 DD DD188052A patent/DD122535A5/xx unknown
- 1975-08-28 AU AU84345/75A patent/AU499371B2/en not_active Expired
- 1975-08-28 AT AT664775A patent/AT342587B/de active
- 1975-08-28 ZA ZA00755512A patent/ZA755512B/xx unknown
- 1975-08-28 BE BE159531A patent/BE832830A/xx not_active IP Right Cessation
- 1975-08-28 IL IL48008A patent/IL48008A/xx unknown
- 1975-08-28 FR FR7526487A patent/FR2283132A1/fr active Granted
- 1975-08-28 ES ES440532A patent/ES440532A1/es not_active Expired
- 1975-08-29 JP JP50104879A patent/JPS5910351B2/ja not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2259974A1 (de) * | 1971-12-10 | 1973-06-14 | Ciba Geigy Ag | Neue ester |
| DE2259960A1 (de) * | 1971-12-10 | 1973-06-14 | Ciba Geigy Ag | Neue ester |
| DE2330089A1 (de) * | 1972-06-16 | 1974-01-03 | Ciba Geigy Ag | Neue ester |
| DE2250572A1 (de) * | 1972-10-14 | 1974-04-18 | Bayer Ag | N,n-dimethyl-o-triazolyl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2360687A1 (de) * | 1972-12-08 | 1974-06-12 | Ciba Geigy Ag | 1,2,4-triazolylphosphorsaeure- bzw. phosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung |
| DE2301400A1 (de) * | 1973-01-12 | 1974-07-18 | Bayer Ag | 0-triazolylthionophosphor(phosphon)saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
Non-Patent Citations (1)
| Title |
|---|
| ELDERFIELD: Heterocyclic Compounds, Vol.7, S.426, 1961 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0062853A3 (en) * | 1981-04-09 | 1983-08-17 | Hoechst Aktiengesellschaft | Process for the preparation of substituted 3-hydroxy-1,2,4-triazoles |
| EP0431390A1 (de) * | 1989-12-02 | 1991-06-12 | Bayer Ag | Substituierte Triazolinone |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5910351B2 (ja) | 1984-03-08 |
| NZ178271A (en) | 1978-04-03 |
| GB1512456A (en) | 1978-06-01 |
| JPS5148668A (en) | 1976-04-26 |
| CS193522B2 (en) | 1979-10-31 |
| IL48008A0 (en) | 1975-11-25 |
| AU499371B2 (en) | 1979-04-12 |
| BE832830A (fr) | 1976-03-01 |
| AT342587B (de) | 1978-04-10 |
| DD122535A5 (en, 2012) | 1976-10-12 |
| ZA755512B (en) | 1976-07-28 |
| ES440532A1 (es) | 1977-03-01 |
| HU172771B (hu) | 1978-12-28 |
| SU577989A3 (ru) | 1977-10-25 |
| DE2537973C2 (en, 2012) | 1989-04-06 |
| ATA664775A (de) | 1977-08-15 |
| AU8434575A (en) | 1977-03-03 |
| CH601266A5 (en, 2012) | 1978-06-30 |
| NL7510012A (nl) | 1976-03-02 |
| FR2283132B1 (en, 2012) | 1978-04-07 |
| FR2283132A1 (fr) | 1976-03-26 |
| CA1070696A (en) | 1980-01-29 |
| IL48008A (en) | 1979-07-25 |
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