DE4033042C2 - - Google Patents
Info
- Publication number
- DE4033042C2 DE4033042C2 DE19904033042 DE4033042A DE4033042C2 DE 4033042 C2 DE4033042 C2 DE 4033042C2 DE 19904033042 DE19904033042 DE 19904033042 DE 4033042 A DE4033042 A DE 4033042A DE 4033042 C2 DE4033042 C2 DE 4033042C2
- Authority
- DE
- Germany
- Prior art keywords
- agar
- hexylimidazole
- substance
- test
- mycoses
- 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 - Fee Related
Links
- SLJJAFUERCIEMU-UHFFFAOYSA-N 4,5-dihexyl-1h-imidazole Chemical compound CCCCCCC=1N=CNC=1CCCCCC SLJJAFUERCIEMU-UHFFFAOYSA-N 0.000 claims description 13
- 208000031888 Mycoses Diseases 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 12
- 230000000699 topical effect Effects 0.000 claims description 4
- 229920001817 Agar Polymers 0.000 description 20
- 239000008272 agar Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 230000000843 anti-fungal effect Effects 0.000 description 6
- 238000002560 therapeutic procedure Methods 0.000 description 6
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 1-substituted imidazoles Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 4
- 230000001857 anti-mycotic effect Effects 0.000 description 4
- 201000003984 candidiasis Diseases 0.000 description 4
- 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 4
- 229960004022 clotrimazole Drugs 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 208000019423 liver disease Diseases 0.000 description 4
- 230000005976 liver dysfunction Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010007134 Candida infections Diseases 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 238000002768 Kirby-Bauer method Methods 0.000 description 3
- 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 3
- 208000007027 Oral Candidiasis Diseases 0.000 description 3
- 241000287411 Turdidae Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000002543 antimycotic Substances 0.000 description 3
- 244000053095 fungal pathogen Species 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 229960004125 ketoconazole Drugs 0.000 description 3
- 229960002509 miconazole Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960000988 nystatin Drugs 0.000 description 3
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 3
- 238000013207 serial dilution Methods 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 2
- 208000006820 Arthralgia Diseases 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000010496 Heart Arrest Diseases 0.000 description 2
- 208000000112 Myalgia Diseases 0.000 description 2
- 206010038669 Respiratory arrest Diseases 0.000 description 2
- 239000006159 Sabouraud's agar Substances 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 206010046914 Vaginal infection Diseases 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 230000004596 appetite loss Effects 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 208000024963 hair loss Diseases 0.000 description 2
- 230000003676 hair loss Effects 0.000 description 2
- 229960000890 hydrocortisone Drugs 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 231100000518 lethal Toxicity 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 235000021266 loss of appetite Nutrition 0.000 description 2
- 208000019017 loss of appetite Diseases 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012449 sabouraud dextrose agar Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 201000005060 thrombophlebitis Diseases 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 206010001580 Albuminuria Diseases 0.000 description 1
- 108010023063 Bacto-peptone Proteins 0.000 description 1
- 206010005098 Blastomycosis Diseases 0.000 description 1
- 206010006473 Bronchopulmonary aspergillosis Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012444 Dermatitis diaper Diseases 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 208000003105 Diaper Rash Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010021036 Hyponatraemia Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000101040 Pityriasis Species 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 208000004430 Pulmonary Aspergillosis Diseases 0.000 description 1
- 208000005485 Thrombocytosis Diseases 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 238000012084 abdominal surgery Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 201000003465 angular cheilitis Diseases 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 206010003883 azoospermia Diseases 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 206010013990 dysuria Diseases 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 201000000079 gynecomastia Diseases 0.000 description 1
- 230000011132 hemopoiesis Effects 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 208000004235 neutropenia Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 208000008634 oligospermia Diseases 0.000 description 1
- 230000036616 oligospermia Effects 0.000 description 1
- 231100000528 oligospermia Toxicity 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 239000008299 semisolid dosage form Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/415—1,2-Diazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904033042 DE4033042A1 (de) | 1990-10-18 | 1990-10-18 | Verwendung von 4,5 - disubstituierten imidazolen zur herstellung von antimykotischen oder fungiziden mitteln |
| DE4042492A DE4042492C2 (de) | 1990-10-18 | 1990-10-18 | Verwendung von 4,5-Di-n-hexylimidazol zur Herstellung von fungiziden Mitteln |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904033042 DE4033042A1 (de) | 1990-10-18 | 1990-10-18 | Verwendung von 4,5 - disubstituierten imidazolen zur herstellung von antimykotischen oder fungiziden mitteln |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE4033042A1 DE4033042A1 (de) | 1992-05-07 |
| DE4033042C2 true DE4033042C2 (cg-RX-API-DMAC7.html) | 1993-05-13 |
Family
ID=6416525
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4042492A Expired - Fee Related DE4042492C2 (de) | 1990-10-18 | 1990-10-18 | Verwendung von 4,5-Di-n-hexylimidazol zur Herstellung von fungiziden Mitteln |
| DE19904033042 Granted DE4033042A1 (de) | 1990-10-18 | 1990-10-18 | Verwendung von 4,5 - disubstituierten imidazolen zur herstellung von antimykotischen oder fungiziden mitteln |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4042492A Expired - Fee Related DE4042492C2 (de) | 1990-10-18 | 1990-10-18 | Verwendung von 4,5-Di-n-hexylimidazol zur Herstellung von fungiziden Mitteln |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE4042492C2 (cg-RX-API-DMAC7.html) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3501286A (en) * | 1964-06-29 | 1970-03-17 | Shell Oil Co | Plant growth control |
| GB2101114B (en) * | 1981-07-10 | 1985-05-22 | Farmos Group Ltd | Substituted imidazole derivatives and their preparation and use |
| DE3212749A1 (de) * | 1982-04-06 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | Neue 5-substituierte 4-methylimidazole und verfahren zu ihrer herstellung |
-
1990
- 1990-10-18 DE DE4042492A patent/DE4042492C2/de not_active Expired - Fee Related
- 1990-10-18 DE DE19904033042 patent/DE4033042A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE4042492C2 (de) | 1995-04-13 |
| DE4033042A1 (de) | 1992-05-07 |
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