IL31302A - N-tritylimidazoles,their preparation and use for combatting fungi - Google Patents
N-tritylimidazoles,their preparation and use for combatting fungiInfo
- Publication number
- IL31302A IL31302A IL31302A IL3130268A IL31302A IL 31302 A IL31302 A IL 31302A IL 31302 A IL31302 A IL 31302A IL 3130268 A IL3130268 A IL 3130268A IL 31302 A IL31302 A IL 31302A
- Authority
- IL
- Israel
- Prior art keywords
- tritylimidazole
- formula
- weight
- active
- active compound
- Prior art date
Links
- 241000233866 Fungi Species 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 45
- NPZDCTUDQYGYQD-UHFFFAOYSA-N 1-tritylimidazole Chemical class C1=NC=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NPZDCTUDQYGYQD-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 13
- -1 oyano Chemical group 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- AGUNPFIFLDXKPR-UHFFFAOYSA-N 2-trityl-1h-imidazole Chemical compound C1=CNC(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 AGUNPFIFLDXKPR-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 20
- 206010061217 Infestation Diseases 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000015097 nutrients Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- GOMIRHDQMYEKAM-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 GOMIRHDQMYEKAM-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000017066 negative regulation of growth Effects 0.000 description 3
- 230000003032 phytopathogenic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000896242 Podosphaera Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical group 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 229940024874 benzophenone Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
- LMSWYOHFMJDYAF-UHFFFAOYSA-N 1-chloro-4-[chloro(diphenyl)methyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 LMSWYOHFMJDYAF-UHFFFAOYSA-N 0.000 description 1
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 240000006497 Dianthus caryophyllus Species 0.000 description 1
- 235000009355 Dianthus caryophyllus Nutrition 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 241000896218 Golovinomyces orontii Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- NIXOIRLDFIPNLJ-UHFFFAOYSA-M magnesium;benzene;bromide Chemical class [Mg+2].[Br-].C1=CC=[C-]C=C1 NIXOIRLDFIPNLJ-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes 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
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681670976 DE1670976C3 (de) | 1968-01-29 | 1968-01-29 | N-Trityl-imidazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31302A0 IL31302A0 (en) | 1969-02-27 |
| IL31302A true IL31302A (en) | 1972-08-30 |
Family
ID=5686363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31302A IL31302A (en) | 1968-01-29 | 1968-12-20 | N-tritylimidazoles,their preparation and use for combatting fungi |
Country Status (21)
| Country | Link |
|---|---|
| US (5) | US3691192A (en, 2012) |
| JP (1) | JPS4815307B1 (en, 2012) |
| AT (2) | AT293100B (en, 2012) |
| BE (1) | BE727488A (en, 2012) |
| BG (1) | BG16996A3 (en, 2012) |
| CA (1) | CA973090A (en, 2012) |
| CH (1) | CH510392A (en, 2012) |
| CS (1) | CS153027B2 (en, 2012) |
| CY (1) | CY771A (en, 2012) |
| DE (1) | DE1670976B2 (en, 2012) |
| ES (1) | ES362950A1 (en, 2012) |
| FR (1) | FR1600990A (en, 2012) |
| GB (3) | GB1260588A (en, 2012) |
| IL (1) | IL31302A (en, 2012) |
| MY (1) | MY7400300A (en, 2012) |
| NL (1) | NL156692B (en, 2012) |
| PH (1) | PH9759A (en, 2012) |
| PL (2) | PL76033B1 (en, 2012) |
| RO (1) | RO53377A (en, 2012) |
| SU (1) | SU422151A3 (en, 2012) |
| YU (1) | YU33270B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2213863C3 (de) * | 1972-03-22 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Disubstituierte Triphenylmethylimidazole, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel |
| US4117142A (en) * | 1972-03-22 | 1978-09-26 | Bayer Aktiengesellschaft | Disubstituted triphenylmethylmidazoles for treating mycotic infections |
| DE2407305C2 (de) * | 1974-02-15 | 1984-06-28 | Bayer Ag, 5090 Leverkusen | Triphenyl-1,2,3-triazol-1-yl-methane, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| DE2502932C2 (de) * | 1975-01-24 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von N-Trityl-azolen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| US4237158A (en) * | 1975-02-05 | 1980-12-02 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles and their use as fungicides |
| US4118461A (en) * | 1975-12-18 | 1978-10-03 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
| US4115578A (en) * | 1975-12-18 | 1978-09-19 | Rohm And Haas Company | 1-Substituted aralkyl imidazoles |
| US4755526A (en) * | 1984-06-18 | 1988-07-05 | Eli Lilly And Company | Method of inhibiting aromatase |
| US4749713A (en) * | 1986-03-07 | 1988-06-07 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
| US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| GB8716650D0 (en) * | 1987-07-15 | 1987-08-19 | Ici Plc | Use of olefinic compounds |
| ATE68486T1 (de) * | 1988-07-28 | 1991-11-15 | Uriach & Cia Sa J | 1-((2-fluorophenyl)(4-fluorophenyl)phenylmethyl - 1h-imidazol. |
| US5177099A (en) * | 1989-04-10 | 1993-01-05 | Sociedad Espanola De Especialidades Farmaco-Terapeuticas S.A. | Dichloro-substituted imidazole derivatives as antifungal agents |
| JP2698279B2 (ja) * | 1992-02-27 | 1998-01-19 | 帝三製薬株式会社 | 防菌防黴性ポリマー組成物 |
| MX9303636A (es) * | 1992-08-07 | 1994-07-29 | Us Agriculture | Composicion y metodo para repeler a las hormigas. |
| US6103733A (en) * | 1998-09-09 | 2000-08-15 | Bachmann; Kenneth A. | Method for increasing HDL cholesterol levels using heteroaromatic phenylmethanes |
| US20060211632A1 (en) * | 2005-03-17 | 2006-09-21 | Bachmann Kenneth A | PXR agonists for cardiovascular disease |
| CN107629006B (zh) * | 2017-11-09 | 2020-04-28 | 青岛农业大学 | 一种克霉唑的合成方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321366A (en) * | 1965-11-15 | 1967-05-23 | Dow Chemical Co | Fungicidal methods and compositions |
-
1968
- 1968-01-25 DE DE1968F0054659 patent/DE1670976B2/de active Granted
- 1968-12-02 CA CA036,634A patent/CA973090A/en not_active Expired
- 1968-12-10 PH PH9829A patent/PH9759A/en unknown
- 1968-12-18 CH CH1888668A patent/CH510392A/de not_active IP Right Cessation
- 1968-12-20 IL IL31302A patent/IL31302A/en unknown
- 1968-12-30 FR FR1600990D patent/FR1600990A/fr not_active Expired
-
1969
- 1969-01-15 CS CS24769*#A patent/CS153027B2/cs unknown
- 1969-01-16 AT AT952069A patent/AT293100B/de not_active IP Right Cessation
- 1969-01-16 AT AT42869A patent/AT283353B/de not_active IP Right Cessation
- 1969-01-20 SU SU1706380A patent/SU422151A3/ru active
- 1969-01-27 NL NL6901307.A patent/NL156692B/xx not_active IP Right Cessation
- 1969-01-27 PL PL1969131420A patent/PL76033B1/pl unknown
- 1969-01-27 BE BE727488D patent/BE727488A/xx not_active IP Right Cessation
- 1969-01-27 PL PL1969155789A patent/PL81995B1/pl unknown
- 1969-01-27 ES ES362950A patent/ES362950A1/es not_active Expired
- 1969-01-28 BG BG011541A patent/BG16996A3/xx unknown
- 1969-01-29 GB GB4898/69A patent/GB1260588A/en not_active Expired
- 1969-01-29 JP JP44006261A patent/JPS4815307B1/ja active Pending
- 1969-01-29 RO RO58920A patent/RO53377A/ro unknown
- 1969-01-29 GB GB43216/71A patent/GB1261690A/en not_active Expired
- 1969-01-29 GB GB43215/71A patent/GB1261500A/en not_active Expired
- 1969-05-29 YU YU186/69A patent/YU33270B/xx unknown
-
1970
- 1970-05-15 US US37841A patent/US3691192A/en not_active Expired - Lifetime
- 1970-09-02 US US69108A patent/US3665077A/en not_active Expired - Lifetime
- 1970-09-02 US US69109A patent/US3666862A/en not_active Expired - Lifetime
- 1970-09-02 US US69107A patent/US3665076A/en not_active Expired - Lifetime
- 1970-09-02 US US69111A patent/US3665078A/en not_active Expired - Lifetime
-
1974
- 1974-11-11 CY CY77174A patent/CY771A/xx unknown
- 1974-12-31 MY MY1974300A patent/MY7400300A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1260588A (en) | 1972-01-19 |
| ES362950A1 (es) | 1970-11-16 |
| IL31302A0 (en) | 1969-02-27 |
| GB1261500A (en) | 1972-01-26 |
| BG16996A3 (bg) | 1973-04-25 |
| NL6901307A (en, 2012) | 1969-07-31 |
| SU422151A3 (ru) | 1974-03-30 |
| MY7400300A (en) | 1974-12-31 |
| JPS4815307B1 (en, 2012) | 1973-05-14 |
| US3691192A (en) | 1972-09-12 |
| SU369745A3 (en, 2012) | 1973-02-08 |
| BE727488A (en, 2012) | 1969-07-28 |
| AT283353B (de) | 1970-08-10 |
| GB1261690A (en) | 1972-01-26 |
| DE1670976B2 (de) | 1976-07-22 |
| CH510392A (de) | 1971-07-31 |
| AT293100B (de) | 1971-09-27 |
| CY771A (en) | 1974-11-11 |
| CA973090A (en) | 1975-08-19 |
| US3666862A (en) | 1972-05-30 |
| DE1670976A1 (de) | 1971-06-16 |
| US3665076A (en) | 1972-05-23 |
| PH9759A (en) | 1976-03-12 |
| RO53377A (en, 2012) | 1974-09-01 |
| CS153027B2 (en, 2012) | 1974-02-22 |
| YU33270B (en) | 1976-08-31 |
| PL76033B1 (en) | 1975-02-28 |
| US3665077A (en) | 1972-05-23 |
| PL81995B1 (en) | 1975-10-31 |
| US3665078A (en) | 1972-05-23 |
| YU18669A (en) | 1976-03-31 |
| NL156692B (nl) | 1978-05-16 |
| FR1600990A (en, 2012) | 1970-08-03 |
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