DE2004302A1 - Neue O,N-Diphenyl-carbaminsäureester, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von Mikroorganismen - Google Patents
Neue O,N-Diphenyl-carbaminsäureester, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von MikroorganismenInfo
- Publication number
- DE2004302A1 DE2004302A1 DE19702004302 DE2004302A DE2004302A1 DE 2004302 A1 DE2004302 A1 DE 2004302A1 DE 19702004302 DE19702004302 DE 19702004302 DE 2004302 A DE2004302 A DE 2004302A DE 2004302 A1 DE2004302 A1 DE 2004302A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- formula
- carbamic acid
- ester
- diphenyl
- 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.)
- Ceased
Links
- 229910052760 oxygen Inorganic materials 0.000 title claims description 17
- 244000005700 microbiome Species 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 dichlorophenoxy Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
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- 239000000969 carrier Substances 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 3
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- KPCOLEDDUNYSQA-UHFFFAOYSA-N (3,5-dimethylphenyl)carbamic acid Chemical compound CC1=CC(C)=CC(NC(O)=O)=C1 KPCOLEDDUNYSQA-UHFFFAOYSA-N 0.000 claims 1
- CZEWVBLUMUTPKM-UHFFFAOYSA-N (3-methylphenyl)carbamothioic s-acid Chemical compound CC1=CC=CC(NC(S)=O)=C1 CZEWVBLUMUTPKM-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- AOVLXBXJFYNQAZ-UHFFFAOYSA-N ethyl n-(3,4-dichlorophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Cl)C(Cl)=C1 AOVLXBXJFYNQAZ-UHFFFAOYSA-N 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 26
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- 150000001875 compounds Chemical class 0.000 description 11
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- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
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- GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical class C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 5
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- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000192023 Sarcina Species 0.000 description 1
- 241000825258 Scopulariopsis brevicaulis Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 241000607764 Shigella dysenteriae Species 0.000 description 1
- 241000607762 Shigella flexneri Species 0.000 description 1
- 241001279364 Stachybotrys chartarum Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000514831 Stemphylium botryosum Species 0.000 description 1
- 241000222355 Trametes versicolor Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 241000607477 Yersinia pseudotuberculosis Species 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940005347 alcaligenes faecalis Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XYLITJZQBKCWRS-UHFFFAOYSA-N bis(3,4-dichlorophenyl)carbamic acid Chemical compound C1=CC(=C(C=C1N(C2=CC(=C(C=C2)Cl)Cl)C(=O)O)Cl)Cl XYLITJZQBKCWRS-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LJAOMRURCSECAH-UHFFFAOYSA-N phenyl N-(2-phenylphenyl)-N-(trifluoromethyl)carbamoperoxoate Chemical class O(C1=CC=CC=C1)OC(N(C(F)(F)F)C1=C(C=CC=C1)C1=CC=CC=C1)=O LJAOMRURCSECAH-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 229940007046 shigella dysenteriae Drugs 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH152169A CH503460A (de) | 1969-01-31 | 1969-01-31 | Verfahren zum antimikrobiellen Ausrüsten bzw. zum Schützen von Textilfasern gegen Mikroorganismen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2004302A1 true DE2004302A1 (de) | 1970-08-06 |
Family
ID=4212381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702004302 Ceased DE2004302A1 (de) | 1969-01-31 | 1970-01-30 | Neue O,N-Diphenyl-carbaminsäureester, Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von Mikroorganismen |
Country Status (10)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001083493A1 (en) * | 2000-05-04 | 2001-11-08 | General Electric Company | Antimicrobial compound |
| WO2006021002A3 (en) * | 2004-08-19 | 2006-04-20 | Icos Corp | Compounds useful for inhibiting chk1 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142646A (en) | 1960-04-11 | 1964-07-28 | Monsanto Co | Antiseptic detergent formulations containing halogenated carbanilates |
| NL6606753A (enrdf_load_stackoverflow) | 1965-05-18 | 1966-11-21 | ||
| FR1493102A (fr) | 1965-05-18 | 1967-08-25 | Agripat Sa | Esters carbamiques et thiocarbamiques et leur préparation |
| CH436207A (de) | 1965-03-02 | 1967-11-15 | Ciba Geigy | Verfahren zum antimikrobiellen Ausrüsten und Schützen von Textilien gegen schädliche Mikroorganismen |
-
1969
- 1969-01-31 CH CH651570A patent/CH493480A/de not_active IP Right Cessation
- 1969-01-31 CH CH651470A patent/CH493499A/de not_active IP Right Cessation
- 1969-01-31 CH CH152169D patent/CH152169A4/xx unknown
- 1969-01-31 CH CH152169A patent/CH503460A/de not_active IP Right Cessation
-
1970
- 1970-01-30 BE BE745213D patent/BE745213A/xx unknown
- 1970-01-30 DE DE19702004302 patent/DE2004302A1/de not_active Ceased
- 1970-01-30 FR FR7003316A patent/FR2034515B1/fr not_active Expired
- 1970-01-30 ES ES376046A patent/ES376046A1/es not_active Expired
- 1970-01-30 JP JP840570A patent/JPS4828897B1/ja active Pending
- 1970-01-30 ES ES376045A patent/ES376045A1/es not_active Expired
- 1970-01-30 NL NL7001392A patent/NL7001392A/xx unknown
- 1970-01-30 ES ES376044A patent/ES376044A1/es not_active Expired
- 1970-01-30 AU AU10804/70A patent/AU1080470A/en not_active Expired
- 1970-01-30 GB GB446670A patent/GB1270901A/en not_active Expired
- 1970-01-30 BR BR21647270A patent/BR7016472D0/pt unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3142646A (en) | 1960-04-11 | 1964-07-28 | Monsanto Co | Antiseptic detergent formulations containing halogenated carbanilates |
| CH436207A (de) | 1965-03-02 | 1967-11-15 | Ciba Geigy | Verfahren zum antimikrobiellen Ausrüsten und Schützen von Textilien gegen schädliche Mikroorganismen |
| NL6606753A (enrdf_load_stackoverflow) | 1965-05-18 | 1966-11-21 | ||
| FR1493102A (fr) | 1965-05-18 | 1967-08-25 | Agripat Sa | Esters carbamiques et thiocarbamiques et leur préparation |
Non-Patent Citations (1)
| Title |
|---|
| MacConkey, Difco <Nicht lesbar> 9. Ausgabe (1953), Seite 131 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001083493A1 (en) * | 2000-05-04 | 2001-11-08 | General Electric Company | Antimicrobial compound |
| US6552214B1 (en) | 2000-05-04 | 2003-04-22 | General Electric Company | Antimicrobial compound |
| WO2006021002A3 (en) * | 2004-08-19 | 2006-04-20 | Icos Corp | Compounds useful for inhibiting chk1 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1270901A (en) | 1972-04-19 |
| ES376045A1 (es) | 1972-04-16 |
| CH503460A (de) | 1970-11-13 |
| NL7001392A (enrdf_load_stackoverflow) | 1970-08-04 |
| CH493480A (de) | 1970-07-15 |
| ES376046A1 (es) | 1972-04-16 |
| JPS4828897B1 (enrdf_load_stackoverflow) | 1973-09-05 |
| ES376044A1 (es) | 1972-06-01 |
| FR2034515A1 (enrdf_load_stackoverflow) | 1970-12-11 |
| BE745213A (fr) | 1970-07-30 |
| CH152169A4 (enrdf_load_stackoverflow) | 1970-11-13 |
| BR7016472D0 (pt) | 1973-04-12 |
| FR2034515B1 (enrdf_load_stackoverflow) | 1973-04-06 |
| CH493499A (de) | 1970-07-15 |
| AU1080470A (en) | 1971-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHV | Ceased/renunciation |