JPS6144878A - アゾ−ル化合物、その製法および用途 - Google Patents
アゾ−ル化合物、その製法および用途Info
- Publication number
- JPS6144878A JPS6144878A JP60155017A JP15501785A JPS6144878A JP S6144878 A JPS6144878 A JP S6144878A JP 60155017 A JP60155017 A JP 60155017A JP 15501785 A JP15501785 A JP 15501785A JP S6144878 A JPS6144878 A JP S6144878A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pharmaceutically acceptable
- compound
- compound according
- acceptable salt
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000003851 azoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 17
- 150000004696 coordination complex Chemical class 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 208000035473 Communicable disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- -1 (-)-4-chloro-α-(1 -cyclopropyl-1-methylethyl)-α-(4-methylphenyl)thiomethylbenzyl alcohol Chemical compound 0.000 description 3
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960004125 ketoconazole Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000510929 Uncinula Species 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- QQCZXHWLXJBWJN-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(2-cyclopropylpropan-2-yl)oxirane Chemical compound C1OC1(C=1C=CC(Cl)=CC=1)C(C)(C)C1CC1 QQCZXHWLXJBWJN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 244000235992 Acalypha lanceolata Species 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000252229 Carassius auratus Species 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 206010046914 Vaginal infection Diseases 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 244000000003 plant pathogen Species 0.000 description 1
- HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- UYXAHRLPUPVSNJ-UHFFFAOYSA-N sodium;2h-triazole Chemical compound [Na].C=1C=NNN=1 UYXAHRLPUPVSNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3425848 | 1984-07-13 | ||
| DE3425848.5 | 1984-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6144878A true JPS6144878A (ja) | 1986-03-04 |
Family
ID=6240558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60155017A Expired - Lifetime JPS6144878A (ja) | 1984-07-13 | 1985-07-12 | アゾ−ル化合物、その製法および用途 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS6144878A (it) |
| AU (1) | AU582761B2 (it) |
| BE (1) | BE902837A (it) |
| CH (1) | CH668772A5 (it) |
| DE (1) | DE3524296C2 (it) |
| DK (1) | DK163058C (it) |
| FR (1) | FR2567515B1 (it) |
| GB (1) | GB2161483B (it) |
| IE (1) | IE58516B1 (it) |
| IL (1) | IL75774A (it) |
| IT (1) | IT1200087B (it) |
| LU (1) | LU86001A1 (it) |
| NL (1) | NL8501962A (it) |
| NZ (1) | NZ212718A (it) |
| PH (1) | PH23287A (it) |
| SE (1) | SE456679B (it) |
| ZA (1) | ZA855286B (it) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5697276A (en) * | 1979-11-13 | 1981-08-05 | Sandoz Ag | Alphaaaryll1hh1*2*44triazolee11ethanols |
| JPS57114577A (en) * | 1980-11-19 | 1982-07-16 | Ici Ltd | Triazole and imidazole compounds, manufacture and bactericide and plant growth regulant composition containing same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH647513A5 (de) * | 1979-11-13 | 1985-01-31 | Sandoz Ag | Triazol-derivate, deren herstellung und verwendung. |
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
-
1985
- 1985-07-04 CH CH2871/85A patent/CH668772A5/de not_active IP Right Cessation
- 1985-07-06 DE DE3524296A patent/DE3524296C2/de not_active Expired - Lifetime
- 1985-07-08 FR FR8510531A patent/FR2567515B1/fr not_active Expired
- 1985-07-09 BE BE1/011292A patent/BE902837A/fr not_active IP Right Cessation
- 1985-07-09 NL NL8501962A patent/NL8501962A/nl active Search and Examination
- 1985-07-09 IT IT48324/85A patent/IT1200087B/it active
- 1985-07-11 AU AU44779/85A patent/AU582761B2/en not_active Expired
- 1985-07-11 GB GB08517526A patent/GB2161483B/en not_active Expired
- 1985-07-11 DK DK318185A patent/DK163058C/da not_active IP Right Cessation
- 1985-07-11 PH PH32517A patent/PH23287A/en unknown
- 1985-07-11 IL IL75774A patent/IL75774A/xx not_active IP Right Cessation
- 1985-07-11 IE IE174785A patent/IE58516B1/en not_active IP Right Cessation
- 1985-07-11 NZ NZ212718A patent/NZ212718A/xx unknown
- 1985-07-11 SE SE8503443A patent/SE456679B/sv not_active IP Right Cessation
- 1985-07-12 LU LU86001A patent/LU86001A1/fr unknown
- 1985-07-12 ZA ZA855286A patent/ZA855286B/xx unknown
- 1985-07-12 JP JP60155017A patent/JPS6144878A/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5697276A (en) * | 1979-11-13 | 1981-08-05 | Sandoz Ag | Alphaaaryll1hh1*2*44triazolee11ethanols |
| JPS57114577A (en) * | 1980-11-19 | 1982-07-16 | Ici Ltd | Triazole and imidazole compounds, manufacture and bactericide and plant growth regulant composition containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1200087B (it) | 1989-01-05 |
| IL75774A0 (en) | 1985-11-29 |
| CH668772A5 (de) | 1989-01-31 |
| DK318185D0 (da) | 1985-07-11 |
| AU582761B2 (en) | 1989-04-13 |
| ZA855286B (en) | 1987-02-25 |
| IT8548324A0 (it) | 1985-07-09 |
| NL8501962A (nl) | 1986-02-03 |
| IE58516B1 (en) | 1993-10-06 |
| GB8517526D0 (en) | 1985-08-14 |
| GB2161483B (en) | 1988-07-13 |
| SE8503443L (sv) | 1986-01-14 |
| PH23287A (en) | 1989-06-30 |
| AU4477985A (en) | 1986-01-16 |
| NZ212718A (en) | 1989-01-27 |
| SE456679B (sv) | 1988-10-24 |
| IE851747L (en) | 1986-01-13 |
| DE3524296A1 (de) | 1986-01-16 |
| DE3524296C2 (de) | 1994-08-25 |
| SE8503443D0 (sv) | 1985-07-11 |
| GB2161483A (en) | 1986-01-15 |
| DK163058C (da) | 1992-06-09 |
| DK163058B (da) | 1992-01-13 |
| IL75774A (en) | 1989-12-15 |
| LU86001A1 (fr) | 1986-02-12 |
| BE902837A (fr) | 1986-01-09 |
| DK318185A (da) | 1986-01-14 |
| FR2567515A1 (fr) | 1986-01-17 |
| FR2567515B1 (fr) | 1988-09-09 |
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