DE3101895A1 - Imidazolhydrazonderivate - Google Patents
ImidazolhydrazonderivateInfo
- Publication number
- DE3101895A1 DE3101895A1 DE19813101895 DE3101895A DE3101895A1 DE 3101895 A1 DE3101895 A1 DE 3101895A1 DE 19813101895 DE19813101895 DE 19813101895 DE 3101895 A DE3101895 A DE 3101895A DE 3101895 A1 DE3101895 A1 DE 3101895A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- imidazol
- hydrochloride
- chlorophenyl
- ethanone
- 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.)
- Withdrawn
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 199
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 106
- -1 3,5-dichlorophenyl Chemical group 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 30
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- ZDGNBZGRLMIIIO-UHFFFAOYSA-N 2,4,6-trichloro-N-[[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethylidene]amino]aniline Chemical compound ClC1=C(C(=CC(=C1)Cl)Cl)NN=C(CN1C=NC=C1)C1=C(C=C(C=C1)Cl)Cl ZDGNBZGRLMIIIO-UHFFFAOYSA-N 0.000 claims 1
- 239000004606 Fillers/Extenders Substances 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 150
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 85
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 85
- 238000002844 melting Methods 0.000 description 78
- 230000008018 melting Effects 0.000 description 78
- 239000000243 solution Substances 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 230000002829 reductive effect Effects 0.000 description 40
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000284 extract Substances 0.000 description 20
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- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 238000012360 testing method Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 150000007857 hydrazones Chemical class 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 239000000460 chlorine Chemical group 0.000 description 12
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- 230000000699 topical effect Effects 0.000 description 10
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- PWFVNVYRKXDPGV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-imidazol-1-ylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CN1C=NC=C1 PWFVNVYRKXDPGV-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229960004125 ketoconazole Drugs 0.000 description 9
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 9
- IDTWYHVEGJBGPT-UHFFFAOYSA-N (2,6-dichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=CC=C1Cl IDTWYHVEGJBGPT-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 7
- 101150065749 Churc1 gene Proteins 0.000 description 7
- 102100038239 Protein Churchill Human genes 0.000 description 7
- 125000001246 bromo group Chemical group Br* 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 244000005700 microbiome Species 0.000 description 7
- HCOVEUUIZWEZBK-UHFFFAOYSA-N n-(2,2-diethoxyethyl)formamide Chemical compound CCOC(OCC)CNC=O HCOVEUUIZWEZBK-UHFFFAOYSA-N 0.000 description 7
- 210000002381 plasma Anatomy 0.000 description 7
- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
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- 239000002585 base Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229960004022 clotrimazole Drugs 0.000 description 6
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 210000003734 kidney Anatomy 0.000 description 6
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 6
- 229960004214 tioconazole Drugs 0.000 description 6
- HLHUAEFBYPEEJL-UHFFFAOYSA-N (2-chlorophenyl)azaniumylideneazanide Chemical compound [N]Nc1ccccc1Cl HLHUAEFBYPEEJL-UHFFFAOYSA-N 0.000 description 5
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- BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/4433—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8002577 | 1980-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3101895A1 true DE3101895A1 (de) | 1982-02-04 |
Family
ID=10510893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813101895 Withdrawn DE3101895A1 (de) | 1980-01-25 | 1981-01-22 | Imidazolhydrazonderivate |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4351948A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56150069A (cg-RX-API-DMAC7.html) |
| AU (1) | AU6635281A (cg-RX-API-DMAC7.html) |
| BE (1) | BE887204A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1157477A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3101895A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK15881A (cg-RX-API-DMAC7.html) |
| ES (1) | ES8204424A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2474495A1 (cg-RX-API-DMAC7.html) |
| IE (1) | IE810120L (cg-RX-API-DMAC7.html) |
| IT (1) | IT1194021B (cg-RX-API-DMAC7.html) |
| NL (1) | NL8100320A (cg-RX-API-DMAC7.html) |
| SE (1) | SE8100237L (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3471486D1 (de) * | 1983-08-15 | 1988-06-30 | Ciba Geigy Ag | Photocurable compositions |
| US5266329A (en) * | 1985-10-31 | 1993-11-30 | Kv Pharmaceutical Company | Vaginal delivery system |
| JPH03115267A (ja) * | 1989-09-28 | 1991-05-16 | Maruho Kk | プロピオフエノン誘導体、その製造方法、それを含む中枢性筋弛緩剤および抗痙攣剤 |
| CA2692170A1 (en) * | 2007-06-18 | 2008-12-24 | Kaken Pharmaceutical Co., Ltd. | Azolylmethylidenehydrazine derivative and use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3830642A (en) * | 1971-04-28 | 1974-08-20 | Upjohn Co | Method for controlling weeds with 1{40 -formyl-1{40 -halobenzeneazomethanes and formulations therefor |
| US3927017A (en) * | 1974-06-27 | 1975-12-16 | Janssen Pharmaceutica Nv | 1-({62 -Aryl-{62 -R-ethyl)imidazoles |
| US4085209A (en) | 1975-02-05 | 1978-04-18 | Rohm And Haas Company | Preparation and safening effect of 1-substituted imidazole metal salt complexes |
| GB1533705A (en) | 1975-03-10 | 1978-11-29 | Ici Ltd | Method of combating fungal infections in plants using imidazoles and 1,2,4-triazoles |
| CH617427A5 (cg-RX-API-DMAC7.html) * | 1975-12-24 | 1980-05-30 | Siegfried Ag | |
| GB1533706A (en) | 1976-03-01 | 1978-11-29 | Ici Ltd | Fungicidal imidazoles and 1,2,4-triazoles |
-
1981
- 1981-01-14 DK DK15881A patent/DK15881A/da not_active Application Discontinuation
- 1981-01-16 SE SE8100237A patent/SE8100237L/xx not_active Application Discontinuation
- 1981-01-16 US US06/225,583 patent/US4351948A/en not_active Expired - Lifetime
- 1981-01-20 AU AU66352/81A patent/AU6635281A/en not_active Abandoned
- 1981-01-22 DE DE19813101895 patent/DE3101895A1/de not_active Withdrawn
- 1981-01-23 NL NL8100320A patent/NL8100320A/nl not_active Application Discontinuation
- 1981-01-23 BE BE0/203574A patent/BE887204A/fr not_active IP Right Cessation
- 1981-01-23 IE IE810120A patent/IE810120L/xx unknown
- 1981-01-23 FR FR8101211A patent/FR2474495A1/fr active Granted
- 1981-01-23 JP JP890381A patent/JPS56150069A/ja active Pending
- 1981-01-23 ES ES498798A patent/ES8204424A1/es not_active Expired
- 1981-01-23 CA CA000369236A patent/CA1157477A/en not_active Expired
- 1981-01-26 IT IT19329/81A patent/IT1194021B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| NL8100320A (nl) | 1981-08-17 |
| SE8100237L (sv) | 1981-07-26 |
| ES498798A0 (es) | 1982-05-01 |
| US4351948A (en) | 1982-09-28 |
| IT8119329A0 (it) | 1981-01-26 |
| AU6635281A (en) | 1981-07-30 |
| IE810120L (en) | 1981-07-25 |
| DK15881A (da) | 1981-07-26 |
| IT1194021B (it) | 1988-08-31 |
| FR2474495B1 (cg-RX-API-DMAC7.html) | 1984-12-21 |
| JPS56150069A (en) | 1981-11-20 |
| FR2474495A1 (fr) | 1981-07-31 |
| CA1157477A (en) | 1983-11-22 |
| BE887204A (fr) | 1981-07-23 |
| ES8204424A1 (es) | 1982-05-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |