WO1993024003A1 - Hochwirksame antimikrobielle biozid-kombinationen - Google Patents
Hochwirksame antimikrobielle biozid-kombinationen Download PDFInfo
- Publication number
- WO1993024003A1 WO1993024003A1 PCT/EP1993/001262 EP9301262W WO9324003A1 WO 1993024003 A1 WO1993024003 A1 WO 1993024003A1 EP 9301262 W EP9301262 W EP 9301262W WO 9324003 A1 WO9324003 A1 WO 9324003A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mixtures according
- antimicrobial
- antimicrobially active
- radicals
- carbon atoms
- Prior art date
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- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- the invention relates to antimicrobial active ingredient mixtures, in particular microbistatically active mixtures containing aminopyridinium compounds and iodopropynyloxyethanol carbamate compounds.
- aminopyridinium compounds as active ingredients in antimicrobial agents has been known for a long time. It is described for example for l, 10-di (4-octylaminopyridinium) decane dihydrochloride in US 4,206,215 or in Journal Med. Chem. (1984), 27, No. 11, page 1462. 4- (0c-tylamino) benzylpyridinium chloride and 4- (0ctylamino) dodecylpyridinium chloride are advertised in EP 174632 as antimicrobial agents.
- the invention relates to antimicrobially active mixtures comprising a) at least one antimicrobially active aminopyridinium compound, b) at least one antimicrobially active iodopropynyloxyethanol carbamate compound, components a and b in the weight ratio of a: b in the range from about 200: 1 to 0.05: 1, preferably 50: 1 to 0.3: 1.
- Suitable antimicrobial substances are aminopyridinium compounds which have an amino function in the para position of the Pyridiniu salt:
- R2 2-C14, aryl, aralkyl, alkenyl R3 ⁇ H
- anti-microbial compounds can be contained in the mixtures according to the invention as chemical individuals or as mixtures.
- anti-microbial compounds are 1, 10-di- . (4-octylaminopyridinium) decane dihydrochloride, 4- (0ctylamino) benzylpyridinium chloride or 4- (0ctylamino) dodecylpyridinium bromide.
- Suitable antimicrobial iodopropynyloxyethanol carbamate compounds are, in particular, 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II) Rl R 3 R 5
- R and R2 are the same or different and are hydrogen, linear or branched alkyl or alkenyl radicals having 1 to 6 carbon atoms or cyclic alkyl radicals having 5 to 7 carbon atoms or R 1 and R - taken together - (CH2) n -, where n 4 to 6, R 3 , R 4 , R 5 and R ⁇ , which may be the same or different, denote hydrogen, alkyl radicals having 1 to 4 carbon atoms, aryl radicals or CCI3 or R 3 and R- or R 4 and R ⁇ taken together - ( CH2) n , where n is 3 to 5, and R- 7 is hydrogen, linear or branched alkyl radicals having 1 to 12 carbon atoms or cyclic alkyl radicals having 4 to 8 carbon atoms, aryl radicals, substituted aryl radicals, arylalkyl radicals or arylsulfonyl radicals.
- linear or branched alkyl radicals or alkenyl radicals having 1 to 6 carbon atoms for which R 1 and R 2 are, are the methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert .-Butyl, pentyl, the hexyl radical and their branched isomers such as the vinyl, allyl, propenyl, butenyl, pentenyl and hexenyl radicals and the corresponding isomers of the alkenyls mentioned having 4, 5 and 6 carbon atoms .
- cyclic alkyl radicals with 5 to 7 carbon atoms for which R 1 and R 2 stand, are the cyclopentane, cyclohexane and cycloheptane radical.
- R 1 and R 2 stand, are the cyclopentane, cyclohexane and cycloheptane radical.
- alkyl radicals with 1 to 4 carbon atoms for which R 3 , R 4 , R5 and R ⁇ are, are the methyl, ethyl, propyl, isopropyl and n-butyl radical, isobutyl, sec-butyl and tert. -Butyl, with methyl being preferred.
- aryl radicals represented by R 3 , R 4 , R 5 and R 6 are the phenyl and the naphthyl radical.
- linear and branched alkyl radicals with 1 to 12 carbon atoms are the methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert .-Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and the dodecyl radical and the branched isomers of alkyls having 5 to 12 carbon atoms.
- cyclic alkyl radicals with 4 to 8 carbon atoms for which R7 stands, are the cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl radical.
- aryl and substituted aryl for which R- 7 stands, are the phenyl, naphthyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, dichlorophenyl and the trichlorophenyl radical.
- R? is a lower alkyl radical having 1 to 4 carbon atoms, and an aryl radical or aryl radical substituted with chlorine or bromine.
- R- 7 is a propyl, butyl or phenyl radical.
- N-substituted 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II) are prepared by processes known per se (Houben-Weyl, Methods of Org. Chemistry, Vol. 8, p. 141-144 (1952)) by reacting equimolar amounts of the alcohols with suitable, for example commercially available, isocyanates, as described, for example, in DE 3216894 AI and DE 3216895 AI. When determining the microbistatic effect on various bacterial and fungal cultures, synergistic effects could be observed with such mixtures.
- the weight ratio of components a and b is set in the range from 50: 1 to 0.3: 1.
- the antimicrobial mixtures according to the invention can be provided in the form of powdered or solvent-containing concentrates, in which the total concentration of components a and b is from about 0.5 to 100, preferably from about 10 can make up to 90 wt .-%.
- Suitable ready-to-use agents have in particular a concentration of about 10 to 50% by weight of the mixture of a and b according to the invention.
- the mixtures intended for practical use still contain a total of 0 to about 99, preferably about 10 to 90,% by weight of further commonly used constituents which are selected depending on the intended form of use and the intended use.
- water-miscible organic solvents are suitable as solvents, for example ethanol, isopropanol and ethylene glycol, propylene glycol, ethylethylene glycol, propylpropylene glycol and water-immiscible solvents such as white spirit, benzene, toluene, ethyl acetate or dimethyl chloride .
- the mixtures according to the invention can also contain surfactants, in particular nonionic surfactants.
- suitable surfactants are Cg-Cig-alkyl glucosides with about 1 to 10 glucose units in the molecule.
- Addition products of about 5 to 16 moles of ethylene oxide with coconut oil or tallow fatty alcohols, with oleyl alcohol, a mixture of oleyl alcohol and cetyl alcohol are of particular interest.
- Mixed addition products of ethylene oxide and propylene oxide onto the compounds mentioned with an active hydrogen atom are also suitable.
- the alkoxylation products mentioned can also be end-capped, for example by ether or acetal groups.
- builder substances can also be present; Suitable as such are, for example, alkali metal salts of gluconic acid, in particular sodium gluconate, the alkali metal salts of nitrilotriacetic acid, ethylene diamine tetraacetic acid, hydroxyethane diphosphonic acid, phosphonobutane tricarboxylic acid, lactic acid, citric acid or tartaric acid.
- Further suitable builder substances are the water-soluble salts of higher molecular weight polycarboxylic acids, for example polymers of maleic acid, itaconic acid, fumaric acid and citraconic acid. Copolymers of these acids with one another or with other polymerizable monomers, such as e.g. Ethylene, propylene, acrylic acid, vinyl acetate, isobutylene, acrylamide and styrene are useful.
- Cleaning enhancers such as fatty acid mono- and diethanol ide, for example coconut fatty acid monoethanolamide and coconut fatty acid diethanolamide, and addition products of up to about 4 moles of ethylene oxide or propylene oxide with fatty alcohols with about 8 to 12 carbon atoms and free fatty alcohols with about 8 to 12 carbons can also be added to the mixtures according to the invention ⁇ atoms and cleaning enhancers based on cellulose are incorporated.
- the mixtures according to the invention contain further antimicrobial substances in addition to the combination according to the invention of aminopyridinium compounds and iodopropynyloxyethanol carbamate compounds.
- Insecticides such as, for example, pyrethroids (permethrin, cypermethrin, decamethrin and fenvalerate) and / or lindane, endosulfan, dieldrin can also be incorporated into the mixtures according to the invention.
- the amounts of these additives should be less than those of the two used according to the invention Components lie.
- the amounts of the possible constituents used for the preparation of the agents according to the invention are generally based on commercial and price specifications and are in principle not of inventive importance.
- solid products preferably in powder or granular form, which contain the antimicrobial mixtures according to the invention can also be provided for the production of ready-to-use preservatives.
- the antimicrobial, synergistically active mixtures according to the invention can be used as disinfectants and preservatives in many areas, for example in households and in commerce, such as hospitals, schools, bathing establishments, public transport, commercial enterprises and industrial plants for the anti-mold finishing of carpets, Wall coverings and sealants. Furthermore, the synergistic mixtures can be used to preserve plant propagation material, in particular seeds and flower bulbs.
- the mixtures according to the invention can be used in the preservation of cosmetics, dishwashing detergents and cleaning agents for technical products still to be processed, such as glazes, lacquer and emulsion paints and emulsion paints, adhesives and glues, drilling and cutting oils or products for paper, cardboard or leather processing industry as well as for the preservation of industrial and industrial water.
- the mixtures according to the invention can also be used for finished material protection, for example for anti-mold finishing of plasters, paints, plastics, floor or wall coverings made of textiles, paper, plastics, leather, cork or for impregnating wood.
- boxes such as those used in commercial mushroom cultivation can be effectively equipped against attack by the culture mycelium.
- the application can take place, for example, by spraying, brushing, brushing, knife coating, dipping or pressure or vacuum impregnation. Examples
- the antimicrobial aminopyridinium compound used was l, 10-di- (4-octylaminopyridinium) decane dihydrochloride (product A).
- the following compound of the formula (III) was used as the antimicrobial iodopropynyloxyethanol carbamate (product B):
- microbistatic activity of the mixtures AB 1 to AB 6 according to the invention in comparison to the individual components (products A and B) was determined with respect to the following test germ suspensions:
- Penicillium funiculosum 5 x 10 * 7 germs / ml
- the inhibitory concentrations of the products to be examined were based on the guidelines for the testing and evaluation of chemical disinfection procedures, chapter 2.1, printed in Zbl. Bakt. Hyg., I. Dept. Orig. B 172, 536-537 (1981).
- Product C was combined with product B to form the following mixture according to the invention:
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19924217884 DE4217884A1 (de) | 1992-05-29 | 1992-05-29 | Hochwirksame antimikrobielle Biozid-Kombinationen |
| DEP4217884.3 | 1992-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993024003A1 true WO1993024003A1 (de) | 1993-12-09 |
Family
ID=6460052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1993/001262 WO1993024003A1 (de) | 1992-05-29 | 1993-05-21 | Hochwirksame antimikrobielle biozid-kombinationen |
Country Status (4)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0998851A1 (en) * | 1998-11-04 | 2000-05-10 | Inui Corporation | Antibacterial and antifungal resin composition |
| EP1123927A1 (en) * | 2000-02-10 | 2001-08-16 | Air Liquide Santé (International) | Process for the preparation of bis-(4-amino-1-pyridinium)-alkanes |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7687513B1 (en) | 2004-10-21 | 2010-03-30 | University Of Notre Dame Du Lac | Aminopyridinium ionic liquids |
| CN102083308A (zh) * | 2008-04-11 | 2011-06-01 | 贝尔法斯特女王大学 | 抗微生物体系 |
| RU2610208C1 (ru) * | 2015-12-01 | 2017-02-08 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Тверской государственный университет" | Ионные жидкости как антимикробные препараты |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206215A (en) * | 1976-02-25 | 1980-06-03 | Sterling Drug Inc. | Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes |
| EP0174632A1 (en) * | 1984-09-12 | 1986-03-19 | Sterling Drug Inc. | Anti-microbial N-(1-(alkyl or arylmethyl)-4(1H)-pyridinylidine)alkanamines and acid addition salts thereof and process for preparation, methods of use and compositions thereof |
| EP0299191A1 (de) * | 1987-06-09 | 1989-01-18 | Henkel Kommanditgesellschaft auf Aktien | Fungizide Wirkstoffgemische |
-
1992
- 1992-05-29 DE DE19924217884 patent/DE4217884A1/de not_active Withdrawn
-
1993
- 1993-05-21 TW TW82104045A patent/TW233247B/zh active
- 1993-05-21 WO PCT/EP1993/001262 patent/WO1993024003A1/de active Application Filing
- 1993-05-21 AU AU43144/93A patent/AU4314493A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206215A (en) * | 1976-02-25 | 1980-06-03 | Sterling Drug Inc. | Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes |
| EP0174632A1 (en) * | 1984-09-12 | 1986-03-19 | Sterling Drug Inc. | Anti-microbial N-(1-(alkyl or arylmethyl)-4(1H)-pyridinylidine)alkanamines and acid addition salts thereof and process for preparation, methods of use and compositions thereof |
| EP0299191A1 (de) * | 1987-06-09 | 1989-01-18 | Henkel Kommanditgesellschaft auf Aktien | Fungizide Wirkstoffgemische |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0998851A1 (en) * | 1998-11-04 | 2000-05-10 | Inui Corporation | Antibacterial and antifungal resin composition |
| US6251381B1 (en) | 1998-11-04 | 2001-06-26 | Inui Corporation | Antibacterial and antifungal resin composition |
| EP1123927A1 (en) * | 2000-02-10 | 2001-08-16 | Air Liquide Santé (International) | Process for the preparation of bis-(4-amino-1-pyridinium)-alkanes |
| JP2001226354A (ja) * | 2000-02-10 | 2001-08-21 | L'air Liquide Sante Internatl | ビス（４−アミノ−１−ピリジニウム）アルカンの製造方法 |
| US6380391B2 (en) | 2000-02-10 | 2002-04-30 | Air Liquide Sante (International) | Process for the preparation of bis(4-amino-1-pyridinium) alkanes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4217884A1 (de) | 1993-12-02 |
| AU4314493A (en) | 1993-12-30 |
| TW233247B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-11-01 |
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