SU613722A3 - Способ получени замещенных пиразолов - Google Patents
Способ получени замещенных пиразоловInfo
- Publication number
- SU613722A3 SU613722A3 SU752189715A SU2189715A SU613722A3 SU 613722 A3 SU613722 A3 SU 613722A3 SU 752189715 A SU752189715 A SU 752189715A SU 2189715 A SU2189715 A SU 2189715A SU 613722 A3 SU613722 A3 SU 613722A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetamide
- methyl
- found
- calculated
- pyrazole
- Prior art date
Links
- 150000003217 pyrazoles Chemical class 0.000 title description 6
- 238000000034 method Methods 0.000 title description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 65
- -1 4-chloro-N, N-diethyl-o-methyl-5-phenylpyrazole-1-acetamide Chemical compound 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- LANBPXHLIUYXOT-UHFFFAOYSA-N 4-methyl-5-phenyl-1h-pyrazole Chemical compound C1=NNC(C=2C=CC=CC=2)=C1C LANBPXHLIUYXOT-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- WDOAUKIEENWZNC-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropanamide Chemical compound CC(Cl)C(=O)N(C)C WDOAUKIEENWZNC-UHFFFAOYSA-N 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 239000007788 liquid Substances 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 229940080818 propionamide Drugs 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 3
- NNWWOIPEHSLORU-UHFFFAOYSA-N 2-bromo-n,n-dimethylbutanamide Chemical compound CCC(Br)C(=O)N(C)C NNWWOIPEHSLORU-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- QQYICHGCQZYYOQ-UHFFFAOYSA-N 5-(furan-2-yl)-4-methyl-1h-pyrazole Chemical compound C1=NNC(C=2OC=CC=2)=C1C QQYICHGCQZYYOQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- WJJXWQMBOVCGSB-UHFFFAOYSA-N 2,5-dibromo-n,n-dimethylpentanamide Chemical compound CN(C)C(=O)C(Br)CCCBr WJJXWQMBOVCGSB-UHFFFAOYSA-N 0.000 claims 1
- HPGOCRQDLWEAOQ-UHFFFAOYSA-N 2-(3-methylpyrazol-1-yl)acetamide Chemical compound CC=1C=CN(CC(N)=O)N=1 HPGOCRQDLWEAOQ-UHFFFAOYSA-N 0.000 claims 1
- KOHAPQXDHKPFBH-UHFFFAOYSA-N 2-bromo-4-chloro-n,n-dimethylbutanamide Chemical compound CN(C)C(=O)C(Br)CCCl KOHAPQXDHKPFBH-UHFFFAOYSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- WORKHWHULFDZDE-UHFFFAOYSA-N 2-chloro-n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)C(C)Cl WORKHWHULFDZDE-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- CALDFXAYVDKUEN-UHFFFAOYSA-N 3-nitro-5-phenyl-1h-pyrazole Chemical compound N1N=C([N+](=O)[O-])C=C1C1=CC=CC=C1 CALDFXAYVDKUEN-UHFFFAOYSA-N 0.000 claims 1
- XCFJZAHCEPIQGM-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-2-(4-methyl-3-phenylpyrazol-1-yl)butanamide Chemical compound CN(C)C(=O)C(CCCl)N1C=C(C)C(C=2C=CC=CC=2)=N1 XCFJZAHCEPIQGM-UHFFFAOYSA-N 0.000 claims 1
- GTTDLUPWHPTYEY-UHFFFAOYSA-N 4-iodo-5-phenyl-1h-pyrazole Chemical compound C1=NNC(C=2C=CC=CC=2)=C1I GTTDLUPWHPTYEY-UHFFFAOYSA-N 0.000 claims 1
- QREPYBUBCNXOEV-UHFFFAOYSA-N 4-methyl-5-[2-(trifluoromethyl)phenyl]-1h-pyrazole Chemical compound C1=NNC(C=2C(=CC=CC=2)C(F)(F)F)=C1C QREPYBUBCNXOEV-UHFFFAOYSA-N 0.000 claims 1
- ICURQXROMAKEGX-UHFFFAOYSA-N 4-methyl-5-thiophen-2-yl-1h-pyrazole Chemical compound C1=NNC(C=2SC=CC=2)=C1C ICURQXROMAKEGX-UHFFFAOYSA-N 0.000 claims 1
- HIEOEDZOHGXCDF-UHFFFAOYSA-N 5-(2-bromophenyl)-4-methyl-1h-pyrazole Chemical compound C1=NNC(C=2C(=CC=CC=2)Br)=C1C HIEOEDZOHGXCDF-UHFFFAOYSA-N 0.000 claims 1
- YJXWEAVEHUPLBS-UHFFFAOYSA-N 5-(2-ethylphenyl)-1h-pyrazole Chemical compound CCC1=CC=CC=C1C1=CC=NN1 YJXWEAVEHUPLBS-UHFFFAOYSA-N 0.000 claims 1
- FZPRWASHAGOUDP-UHFFFAOYSA-N 5-(2-fluorophenyl)-4-methyl-1h-pyrazole Chemical compound C1=NNC(C=2C(=CC=CC=2)F)=C1C FZPRWASHAGOUDP-UHFFFAOYSA-N 0.000 claims 1
- QHRSESMSOJZMCO-UHFFFAOYSA-N 5-methyl-3-phenyl-1h-pyrazole Chemical compound N1C(C)=CC(C=2C=CC=CC=2)=N1 QHRSESMSOJZMCO-UHFFFAOYSA-N 0.000 claims 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 229940095130 dimethyl capramide Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229950001413 metamfepramone Drugs 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- ASCCMGGNOJXQPO-UHFFFAOYSA-N n,n-dimethyl-2-(4-methylpyrazol-1-yl)acetamide Chemical compound CN(C)C(=O)CN1C=C(C)C=N1 ASCCMGGNOJXQPO-UHFFFAOYSA-N 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52423174A | 1974-11-15 | 1974-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU613722A3 true SU613722A3 (ru) | 1978-06-30 |
Family
ID=24088332
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752189715A SU613722A3 (ru) | 1974-11-15 | 1975-11-14 | Способ получени замещенных пиразолов |
| SU7502190909A SU581838A3 (ru) | 1974-11-15 | 1975-11-14 | Гербицидный состав |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502190909A SU581838A3 (ru) | 1974-11-15 | 1975-11-14 | Гербицидный состав |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4072498A (https=) |
| JP (1) | JPS5182269A (https=) |
| BE (1) | BE835604A (https=) |
| BR (1) | BR7507364A (https=) |
| CH (1) | CH629364A5 (https=) |
| DE (1) | DE2550566A1 (https=) |
| FR (1) | FR2324633A1 (https=) |
| GB (1) | GB1483162A (https=) |
| IT (1) | IT1052194B (https=) |
| NZ (1) | NZ178996A (https=) |
| PH (1) | PH12819A (https=) |
| PL (1) | PL101829B1 (https=) |
| SU (2) | SU613722A3 (https=) |
| ZA (1) | ZA756627B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2901593A1 (de) * | 1979-01-17 | 1980-08-07 | Basf Ag | N-azolylessigsaeureanilide |
| DE3041702A1 (de) * | 1980-11-05 | 1982-06-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung |
| US4515623A (en) * | 1981-10-09 | 1985-05-07 | Basf Aktiengesellschaft | Control of unwanted plant growth with 2-aryloxy-2-azolylalkanecarboxamides |
| US4874871A (en) * | 1987-03-25 | 1989-10-17 | Syntex (U.S.A.) Inc. | Process for preparing (+)-2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and related compounds |
| US4870095A (en) * | 1988-06-13 | 1989-09-26 | Sterling Drug, Inc. | 1H-pyrazole-1-alkanamides, antiarrhythmic compositions and use |
| JP2784925B2 (ja) * | 1988-09-07 | 1998-08-13 | 日本農薬株式会社 | ３又は５−フェニルピラゾール類又はその塩及び除草剤 |
| US4916150A (en) * | 1989-03-22 | 1990-04-10 | Sterling Drug Inc. | 1H-pyrazole-1-alkanamines antiarrhythmic compositions and use |
| US4988725A (en) * | 1989-03-22 | 1991-01-29 | Sterling Drug Inc. | 1H-pyrazole-1-(branched)alkanamides as antiarrhythmic agents, compositions and use |
| US4898880A (en) * | 1989-03-22 | 1990-02-06 | Sterling Drug Inc. | N-(heterocycle)alkyl)-1H-pyrazole-1-alkanamides as antiarrhythmic agents, compositions and use |
| US4888352A (en) * | 1989-03-22 | 1989-12-19 | Sterling Drug Inc. | 3,4, or 5-aryl-1H-pyrazole-1-alkanamides as antiarrhythmic agents, compositions and use |
| US4925857A (en) * | 1989-03-22 | 1990-05-15 | Sterling Drug Inc. | Pyridinyl-1H-pyrazole-1-alkanamides as antiarrhythmic agents |
| US4994482A (en) * | 1989-07-31 | 1991-02-19 | Bristol-Myers Squibb Company | Arylpyrazol derivatives as anti-platelet agents, compositions and use |
| JPH0393774A (ja) * | 1989-09-07 | 1991-04-18 | Nippon Nohyaku Co Ltd | ３又は５―フェニルピラゾール類又はその塩及び除草剤 |
| US5366987A (en) * | 1991-08-22 | 1994-11-22 | Warner-Lambert Company | Isoxazolyl-substituted alkyl amide ACAT inhibitors |
| US5532416A (en) * | 1994-07-20 | 1996-07-02 | Monsanto Company | Benzoyl derivatives and synthesis thereof |
| FR2682379B1 (fr) | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
| FR2690440B1 (fr) * | 1992-04-27 | 1995-05-19 | Rhone Poulenc Agrochimie | Arylpyrazoles fongicides. |
| IL112014A (en) * | 1993-12-24 | 1999-10-28 | Rhone Poulenc Agrochimie | 1,3-Oxazin-4-one derivatives and herbicides containing the same |
| US5880290A (en) * | 1994-01-31 | 1999-03-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| US5869688A (en) * | 1994-07-20 | 1999-02-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| US5698708A (en) * | 1996-06-20 | 1997-12-16 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| DE19744026A1 (de) * | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| CA2368631A1 (en) | 1999-03-26 | 2000-10-05 | Euro-Celtique S.A. | Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof |
| NZ520875A (en) | 2000-03-24 | 2005-04-29 | Euro Celtique S | Aryl substituted pyrazoles, triazoles and tetrazoles as sodium channel blocker |
| JP4430938B2 (ja) * | 2001-12-20 | 2010-03-10 | 株式会社エス・ディー・エス バイオテック | 新規置換ピラゾール誘導体、その製造方法およびそれらを含有する除草剤組成物 |
| CN103265537B (zh) * | 2013-05-14 | 2015-05-27 | 浙江医药高等专科学校 | 抗肿瘤化合物、其制备方法和用途 |
| GB201616439D0 (en) * | 2016-09-28 | 2016-11-09 | Mironid Limited | Compounds and uses |
| WO2019081485A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2019081477A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| GB201805527D0 (en) | 2018-04-04 | 2018-05-16 | Mironid Ltd | Compounds and their use as pde4 activators |
| CN110963957B (zh) | 2018-09-28 | 2021-10-22 | 深圳恩多凯医药科技有限公司 | N-芳香酰胺类化合物及其制备方法和用途 |
| CN119019332B (zh) * | 2024-08-15 | 2026-02-24 | 赣南师范大学 | 一种1,5-二取代-4-溴吡唑类化合物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH485733A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| BE795881A (fr) * | 1972-02-23 | 1973-08-23 | Upjohn Co | Tribromopyrazoles et leur preparation |
-
1975
- 1975-10-20 NZ NZ178996A patent/NZ178996A/xx unknown
- 1975-10-21 ZA ZA756627A patent/ZA756627B/xx unknown
- 1975-10-23 GB GB43505/75A patent/GB1483162A/en not_active Expired
- 1975-11-03 CH CH1417475A patent/CH629364A5/de not_active IP Right Cessation
- 1975-11-07 BR BR7507364*A patent/BR7507364A/pt unknown
- 1975-11-11 DE DE19752550566 patent/DE2550566A1/de not_active Withdrawn
- 1975-11-14 FR FR7534913A patent/FR2324633A1/fr not_active Withdrawn
- 1975-11-14 IT IT52221/75A patent/IT1052194B/it active
- 1975-11-14 SU SU752189715A patent/SU613722A3/ru active
- 1975-11-14 SU SU7502190909A patent/SU581838A3/ru active
- 1975-11-14 BE BE161900A patent/BE835604A/xx unknown
- 1975-11-15 JP JP50137708A patent/JPS5182269A/ja active Pending
- 1975-11-15 PL PL1975184782A patent/PL101829B1/pl unknown
-
1976
- 1976-05-14 US US05/686,548 patent/US4072498A/en not_active Expired - Lifetime
-
1977
- 1977-11-23 PH PH20469A patent/PH12819A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8595775A (en) | 1977-04-28 |
| JPS5182269A (https=) | 1976-07-19 |
| IT1052194B (it) | 1981-06-20 |
| PL101829B1 (pl) | 1979-02-28 |
| DE2550566A1 (de) | 1976-05-20 |
| FR2324633A1 (fr) | 1977-04-15 |
| ZA756627B (en) | 1977-05-25 |
| BR7507364A (pt) | 1976-08-10 |
| US4072498A (en) | 1978-02-07 |
| PH12819A (en) | 1979-08-31 |
| CH629364A5 (de) | 1982-04-30 |
| NZ178996A (en) | 1978-06-02 |
| GB1483162A (en) | 1977-08-17 |
| BE835604A (fr) | 1976-05-14 |
| SU581838A3 (ru) | 1977-11-25 |
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