DD218098A5 - Verfahren zur herstellung von triazol-derivaten - Google Patents
Verfahren zur herstellung von triazol-derivaten Download PDFInfo
- Publication number
- DD218098A5 DD218098A5 DD83255229A DD25522983A DD218098A5 DD 218098 A5 DD218098 A5 DD 218098A5 DD 83255229 A DD83255229 A DD 83255229A DD 25522983 A DD25522983 A DD 25522983A DD 218098 A5 DD218098 A5 DD 218098A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- alkoxy
- formula
- ethyl
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- -1 5-chloropyrid-2-yl group Chemical group 0.000 claims abstract description 19
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 12
- 239000000417 fungicide Substances 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 13
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- 238000004458 analytical method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
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- 208000031888 Mycoses Diseases 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
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- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 230000000843 anti-fungal effect Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 229960000583 acetic acid Drugs 0.000 description 4
- 229940121375 antifungal agent Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
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- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
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- 241000282412 Homo Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
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- 238000007911 parenteral administration Methods 0.000 description 3
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- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- JOKCRTQSVAOBSG-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-3-hydroxy-2-methyl-4-(1,2,4-triazol-1-yl)butanenitrile Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(C(C#N)C)CN1C=NC=N1 JOKCRTQSVAOBSG-UHFFFAOYSA-N 0.000 description 2
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- 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
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
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- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940045860 white wax Drugs 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
- C07D231/12—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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8227978 | 1982-09-30 | ||
| GB838302888A GB8302888D0 (en) | 1983-02-02 | 1983-02-02 | Antifungal agents |
| GB838312624A GB8312624D0 (en) | 1983-05-07 | 1983-05-07 | Triazole antifungal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD218098A5 true DD218098A5 (de) | 1985-01-30 |
Family
ID=27261761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83255229A DD218098A5 (de) | 1982-09-30 | 1983-09-29 | Verfahren zur herstellung von triazol-derivaten |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0106515B1 (enExample) |
| KR (1) | KR880002208B1 (enExample) |
| AU (1) | AU542694B2 (enExample) |
| DD (1) | DD218098A5 (enExample) |
| DE (1) | DE3378764D1 (enExample) |
| DK (1) | DK166622B1 (enExample) |
| ES (1) | ES526066A0 (enExample) |
| FI (1) | FI85694C (enExample) |
| GR (1) | GR81270B (enExample) |
| HU (1) | HU194837B (enExample) |
| IE (1) | IE56019B1 (enExample) |
| IL (1) | IL69825A (enExample) |
| NO (1) | NO164168C (enExample) |
| NZ (1) | NZ205795A (enExample) |
| PT (1) | PT77430B (enExample) |
| YU (4) | YU195683A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001011145A1 (de) | 1999-08-09 | 2001-02-15 | Maschinen & Anlagen Service Gmbh | Bürstenwelle zur reinigung von gleisanlagen |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4610716A (en) * | 1982-12-14 | 1986-09-09 | Ciba-Geigy Corporation | Fluorinated azolyl ethanol growth regulators and microbicides |
| JPS6025990A (ja) * | 1983-07-20 | 1985-02-08 | Shionogi & Co Ltd | トリアゾ−ル系ジオキソラン誘導体 |
| GB8322983D0 (en) * | 1983-08-26 | 1983-09-28 | Pfizer Ltd | Triazole antifungal agents |
| CN1008735B (zh) * | 1984-11-02 | 1990-07-11 | 拜尔公司 | 以取代的氮杂茂基甲基-环丙基-甲醇衍生物为活性成分的组合物 |
| GB8510195D0 (en) * | 1985-04-22 | 1985-05-30 | Ici Plc | Heterocyclic compounds |
| GB8601952D0 (en) * | 1986-01-28 | 1986-03-05 | Ici Plc | Heterocyclic compounds |
| EP0386143A1 (en) * | 1987-11-20 | 1990-09-12 | Schering Corporation | Tri- and tetra-substituted-oxetanes and tetrahydrofurans and intermediates thereof |
| DE3839170A1 (de) * | 1988-11-19 | 1990-05-31 | Bayer Ag | Cyclopropyl-substituierte azolylmethylcarbinole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US5134152A (en) * | 1989-12-07 | 1992-07-28 | Sankyo Company, Limited | Oxetane derivatives and their use as anti-fungal or fungicidal agents |
| ATE154350T1 (de) * | 1990-10-17 | 1997-06-15 | Hoechst Schering Agrevo Gmbh | Pyrimidin-derivate, verfahren zu ihrer herstellung sie enthaltende mittel und ihre verwendung als fungizide |
| GB9107055D0 (en) * | 1991-04-04 | 1991-05-22 | Pfizer Ltd | Triazole antifungal agents |
| JP3471831B2 (ja) * | 1991-12-09 | 2003-12-02 | 富山化学工業株式会社 | 新規なトリアゾール誘導体およびその塩 |
| DE4206529A1 (de) * | 1992-03-02 | 1993-09-09 | Bayer Ag | Azolylmethyl-cyclopropyl-derivate |
| CN1054853C (zh) * | 1995-01-11 | 2000-07-26 | 上海三维制药公司 | 氟康唑中间体1－[2－(2,4－二氟苯基)2,3－环氧丙基]－1h－1,2,4－三氮唑及其甲磺酸盐的制备方法 |
| CA2838586C (en) | 2011-06-07 | 2016-10-11 | Kureha Corporation | Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent |
| WO2013077265A1 (ja) | 2011-11-25 | 2013-05-30 | 株式会社クレハ | アゾール誘導体、およびその利用 |
| PL3078265T3 (pl) | 2013-12-05 | 2017-10-31 | Kureha Corp | Substancja chemiczna do zastosowań rolniczych lub ogrodniczych, metoda ochrony roślin przed chorobami oraz produkt ochrony roślin przed chorobami |
| US9814236B2 (en) | 2013-12-05 | 2017-11-14 | Kureha Corporation | Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046633A1 (en) * | 1980-08-22 | 1982-03-03 | Imperial Chemical Industries Plc | Heterocyclic compounds useful as pesticides and processes for making them |
| DE3048267A1 (de) * | 1980-12-20 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
| GR78234B (enExample) * | 1981-03-10 | 1984-09-26 | Ciba Geigy Ag | |
| EP0084236A3 (en) * | 1981-12-22 | 1983-08-03 | Fbc Limited | Fungicidal heterocyclic compounds and compositions containing them |
| GB2120235A (en) * | 1982-03-23 | 1983-11-30 | Ici Plc | Triazole and imidazole derivatives having fungicidal and plant-growth regulating activity |
| GB8301699D0 (en) * | 1983-01-21 | 1983-02-23 | Pfizer Ltd | Antifungal agents |
-
1983
- 1983-09-09 EP EP83305278A patent/EP0106515B1/en not_active Expired
- 1983-09-09 DE DE8383305278T patent/DE3378764D1/de not_active Expired
- 1983-09-26 KR KR1019830004490A patent/KR880002208B1/ko not_active Expired
- 1983-09-27 IL IL69825A patent/IL69825A/xx not_active IP Right Cessation
- 1983-09-28 DK DK443683A patent/DK166622B1/da not_active IP Right Cessation
- 1983-09-28 NZ NZ205795A patent/NZ205795A/en unknown
- 1983-09-28 FI FI833496A patent/FI85694C/fi not_active IP Right Cessation
- 1983-09-29 NO NO833549A patent/NO164168C/no unknown
- 1983-09-29 IE IE2302/83A patent/IE56019B1/en not_active IP Right Cessation
- 1983-09-29 AU AU19771/83A patent/AU542694B2/en not_active Ceased
- 1983-09-29 GR GR72582A patent/GR81270B/el unknown
- 1983-09-29 PT PT77430A patent/PT77430B/pt not_active IP Right Cessation
- 1983-09-29 ES ES526066A patent/ES526066A0/es active Granted
- 1983-09-29 YU YU01956/83A patent/YU195683A/xx unknown
- 1983-09-29 HU HU833388A patent/HU194837B/hu not_active IP Right Cessation
- 1983-09-29 DD DD83255229A patent/DD218098A5/de unknown
-
1985
- 1985-08-14 YU YU01295/85A patent/YU129585A/xx unknown
- 1985-08-14 YU YU01297/85A patent/YU129785A/xx unknown
- 1985-08-14 YU YU01296/85A patent/YU129685A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001011145A1 (de) | 1999-08-09 | 2001-02-15 | Maschinen & Anlagen Service Gmbh | Bürstenwelle zur reinigung von gleisanlagen |
Also Published As
| Publication number | Publication date |
|---|---|
| DK443683D0 (da) | 1983-09-28 |
| EP0106515A2 (en) | 1984-04-25 |
| EP0106515B1 (en) | 1988-12-28 |
| AU542694B2 (en) | 1985-03-07 |
| YU129785A (en) | 1986-02-28 |
| YU129685A (en) | 1986-02-28 |
| FI833496A7 (fi) | 1984-03-31 |
| DK166622B1 (da) | 1993-06-21 |
| NO164168B (no) | 1990-05-28 |
| FI85694C (fi) | 1992-05-25 |
| IL69825A (en) | 1986-12-31 |
| IL69825A0 (en) | 1983-12-30 |
| NZ205795A (en) | 1985-09-13 |
| PT77430A (en) | 1983-10-01 |
| ES8504150A1 (es) | 1985-04-16 |
| AU1977183A (en) | 1984-04-05 |
| PT77430B (en) | 1986-04-17 |
| HU194837B (en) | 1988-03-28 |
| GR81270B (enExample) | 1984-12-11 |
| YU129585A (en) | 1986-02-28 |
| YU195683A (en) | 1986-02-28 |
| FI85694B (fi) | 1992-02-14 |
| KR840006221A (ko) | 1984-11-22 |
| DK443683A (da) | 1984-03-31 |
| ES526066A0 (es) | 1985-04-16 |
| EP0106515A3 (en) | 1985-12-04 |
| DE3378764D1 (en) | 1989-02-02 |
| IE56019B1 (en) | 1991-03-27 |
| NO833549L (no) | 1984-04-02 |
| IE832302L (en) | 1984-03-30 |
| FI833496A0 (fi) | 1983-09-28 |
| KR880002208B1 (ko) | 1988-10-18 |
| NO164168C (no) | 1990-09-05 |
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