WO1993006729A1 - Antimicrobial-agent mixtures - Google Patents
Antimicrobial-agent mixtures Download PDFInfo
- Publication number
- WO1993006729A1 WO1993006729A1 PCT/EP1992/002200 EP9202200W WO9306729A1 WO 1993006729 A1 WO1993006729 A1 WO 1993006729A1 EP 9202200 W EP9202200 W EP 9202200W WO 9306729 A1 WO9306729 A1 WO 9306729A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- antimicrobial
- mixtures according
- antimicrobially active
- radicals
- carbon atoms
- Prior art date
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- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
-
- 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
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- A01N47/20—N-Aryl 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
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
- C09D5/025—Preservatives, e.g. antimicrobial agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C1/00—Chemical treatment prior to tanning
- C14C1/02—Curing raw hides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
Definitions
- the invention relates to antimicrobial active substance mixtures, in particular fungistatically active mixtures containing chloroacetamide or its derivatives and iodopropynyloxyethanol carbamate compounds.
- the invention relates to antimicrobial mixtures comprising a) at least one antimicrobial chloroacetamide or substituted chloroacetamide and b) at least one antimicrobially active iodopropynyloxyethanol carbamate compound, components a and b being in a weight ratio of a: b in the range from 300: 1 to 0.05: 1.
- Chloracetamides which have the formula I are suitable as antimicrobial substances
- antimicrobial compounds can be contained in the mixtures according to the invention as chemical individuals or as mixtures.
- antimicrobial compounds are N- (4-bromo-2-methylphenyl) -2-chloroacetamide, according to EP 137 729 A2 or N-methyl-N-heptylchloroacetamide.
- Suitable antimicrobial iodopropynyloxyethanol carbamate compounds are, in particular, 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II)
- R 1 and R 2 are identical 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 * and R 2 taken together - (CH 2 ) n -, , where n is 4 to 6,
- R 3 , R 4 , R 5 and R 6 which may be the same or different, are hydrogen, alkyl radicals having 1 to 4 carbon atoms, aryl radicals or CCI 3 or R 3 and R 5 or R 4 and R 6 taken together represent - (CH 2 ) 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 means.
- linear or branched alkyl radicals or alkenyl radicals with 1 to 6 carbon atoms for which R 1 and R 2 stand, 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 with 4, 5 and 6 carbon atoms.
- cyclic alkyl radicals having 5 to 7 carbon atoms for which R 1 and R 2 stand, are the cyclopentane, cyclohexane and cycloheptane radicals.
- Compounds of the formula (II) in which both substituents R 1 and R 2 are simultaneously hydrogen or simultaneously methyl radicals are preferred, and compounds in which one of R * and R 2 is hydrogen while the other represents a methyl radical.
- alkyl radicals with 1 to 4 carbon atoms which R 3 , R 4 , R 5 and R 6 represent, 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.
- 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 which R 7 represents are the phenyl, naphthyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, dichlorophenyl and the trichlorophenyl radical.
- Examples of aralkyl and arylsulfonyl for which R 7 stands are the benzyl and p-toluenesulfonyl radicals.
- R 7 is a lower alkyl radical having 1 to 4 carbon atoms and an aryl radical or aryl radical substituted by chlorine or bromine are preferred.
- 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 methods 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 are synthesized, as described, for example, in DE 32 16 894 Al and in DE 32 16 895 Al.
- the weight ratio of components a and b is set in the range from 100: 1 to 0.1: 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 10 to 90,% by weight can.
- Suitable ready-to-use agents have in particular a concentration of 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 90 to 10% 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 dimethylene chloride.
- the mixtures according to the invention can also contain surfactants, in particular nonionic surfactants.
- suitable surfactants are adducts of 4 to 40, preferably 4 to 20, moles of ethylene oxide with one mole of fatty alcohol, alkylcyclohexanol, alkylphenol, fatty acid, fatty acid amide or alkanesulfonamide.
- Addition products of 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 and with mono-, di- or trialkylphenols and with monoalkylcyclohexanols with 6 to 14 carbon atoms in the alkyl radicals 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.
- the amount of surfactant can be about 0.001 to about 2, preferably about 0.01 to 0.15% by weight, based on the compound.
- Builders may also be present in the mixtures according to the invention; Suitable as such are, for example, alkali metal salts of gluconic acid, in particular sodium gluconate, the alkali metal salts of nitrilotriacetic acid, ethylenediaminetetraacetic acid, hydroxyethane diphosphonic acid, phosphonobutane tricarboxylic acid, lactic acid, citric acid or tartaric acid.
- the water-soluble salts of higher molecular weight polycarboxylic acids for example polymers of maleic acid, itaconic acid, fumaric acid and citraconic acid, are also suitable as builders. 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.
- the amounts of the builder substances can be about 0.01 to 2, preferably 0.02 to 1.0,% by weight, based on the compound.
- Cleaning enhancers such as fatty acid mono- and diethanolamides, for example coconut fatty acid monoethanolamide and coconut fatty acid diethanolamide, and addition products of up to 4 moles of ethylene oxide or propylene oxide with fatty alcohols with 8 to 12 carbon atoms and free fatty alcohols with 8 to 12 carbon atoms as well as cleaning enhancers based on cellulose can also be incorporated into the mixtures according to the invention .
- the amounts of cleaning boosters can be about 0.001 to 0.02, preferably about 0.005 to 0.01% by weight, based on the compound.
- the mixtures according to the invention contain, in addition to the combination of chloroacetamide compounds and iodopropynyloxyethanol carbamate compounds according to the invention, further antimicrobial substances.
- Insecticides such as pyrethrofde (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 are said to be lower than those of the two components used according to the invention.
- the amounts of the possible components used to assemble 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 granule 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 trade, such as hospitals, schools, bathing establishments, public transport, commercial plants and industrial plants in the anti-mold finishing of carpets, wall coverings and sealing compounds.
- 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 technical products still to be processed, such as glazes, lacquer and dispersion and emulsion paints, adhesives and pastes, drilling and cutting oils or products from the paper, cardboard or leather-processing industry, and for the preservation of industrial and Find domestic water application.
- 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.
- the application concentrations are generally about 0.001 to 5, preferably about 0.01 to 2,% by weight of active substance mixture. Examples
- the antimicrobial chloroacetamide compounds used were N- (4-bromo-2-methylenephenyl) -2-chloroacetamide (product A).
- the following compounds of the formula (III) were used as antimicrobial iodopropynyloxyethanol carbamates (product B):
- microbistatic activity of the mixtures AB 1 to AB 5 according to the invention in comparison with the individual components (products A and B) was determined with respect to the following test germ suspensions: 1. Staphylococcus aureus 2 ⁇ 10 9 germs / ml
- Candida albicans 1 ⁇ 10 8 germs / ml
- the inhibitory concentrations of the products to be tested were based on the guidelines for the testing and evaluation of chemical disinfection processes, chapter 2.1, printed in Zbl. Bakt. Hyg., I. Dept. Orig. 172, 536-537 (1981).
- the substance mixtures AB 1 to AB 5 and di individual components A and B were dissolved in stock solutions in dimethylformamide, from which the corresponding dilution series were prepared by adding wort broth in a volume ratio of 1:50.
- Mixtures AB 1 to AB 5 each contain the quantities of the individual components men that were used in the weight ratios indicated above.
- Chloroacetamide (Product C) was used as the antimicrobial chloroacetamide compound.
- Product B was used as the antimicrobial iodopropynyloxyethanol carbamate compound.
- Product C was combined with product B to the following mixtures according to the invention:
- N-Methyl-N-heptylchloroacetamide (product D) was used as the antimicrobial chloracetamide compound.
- Product B was used as an antimicrobial iodopropynyloxyethanol carbamate compound.
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Disclosed are mixtures with an antimicrobial action, containing chloracetamide compounds and iodopropynyloxyethanol carbamate compounds in the ratio by weight of 300:1 to 0.05:1, and the use of such mixtures in providing materials in the home, and in commerce and industry, with fungicidal protection.
Description
"Antimikrobiel le Wirkstoffgemische" "Antimicrobial mixtures of active ingredients"
Die Erfindung betrifft antimikrobielle Wirkstoffgemische, insbesondere fungistatisch wirksame Gemische mit einem Gehalt an Chloracetamid bzw. dessen Derivaten und Jodpropinyloxy-ethanol-carbamatverbindungen. The invention relates to antimicrobial active substance mixtures, in particular fungistatically active mixtures containing chloroacetamide or its derivatives and iodopropynyloxyethanol carbamate compounds.
Die Verwendung von Monochloracetamid und substituierten Chloracetamiden als Wirkstoffe in antimikrobiel len Mitteln ist seit langem bekannt. Sie wird beispielsweise für Monochloracetamid von Gregor Schmidt in "Seifen- Öle-Fette-Wachse", 102 (1976), Seite 557 beschrieben. The use of monochloroacetamide and substituted chloroacetamides as active ingredients in antimicrobial agents has long been known. It is described for example for monochloroacetamide by Gregor Schmidt in "Seifen-Öle-Fette-Wwachs", 102 (1976), page 557.
Auch die Verwendung von Jodpropinyloxy-ethanol-carbamaten als Bakterizide und Fungizide ist seit längerer Zeit bekannt, siehe beispielsweise DE 32 16895 Al. The use of iodopropynyloxyethanol carbamates as bactericides and fungicides has also been known for a long time, see for example DE 32 16895 Al.
Auf dem Gebiet der Desinfektions- und Konservierungsmittel besteht unter den Gesichtspunkten des Umweltschutzes und der Wirtschaftlichkeit ein Bedürfnis nach Wirkstoffen und Wirkstoffkombinationen, die schon bei geringen Anwendungskonzentrationen eine hinreichende antimikrobielle Wirkung zeigen. In diesem Zusammenhang sind nicht nur neue Verbindungen von Interesse, sondern auch synergistisch wirkende Kombinationen bereits bekannter Wirkstoffe. In the field of disinfectants and preservatives, there is a need for active substances and combinations of active substances which have an adequate antimicrobial effect even at low application concentrations from the point of view of environmental protection and economy. In this context, not only new compounds are of interest, but also synergistic combinations of known active ingredients.
Es wurde gefunden, daß Kombinationen aus Chloracetamid bzw. substituierten Chloracetamiden und Jodpropinyloxy-ethanol-carbamaten eine synergistische antimikrobielle Wirkung zeigen. It has been found that combinations of chloroacetamide or substituted chloroacetamides and iodopropynyloxyethanol carbamates have a synergistic antimicrobial effect.
Gegenstand der Erfindung sind antimikrobiell wirksame Gemische enthaltend a) mindestens ein antimikrobiell wirksames Chloracetamid bzw. substituiertes Chloracetamid und
b) mindestens eine antimikrobiell wirksame Jodpropinyloxy-ethanol-carbamatverbindung, wobei die Komponenten a und b im Gewichtsverhältnis von a : b im Bereich von 300 : 1 bis 0,05 : 1 vorliegen. The invention relates to antimicrobial mixtures comprising a) at least one antimicrobial chloroacetamide or substituted chloroacetamide and b) at least one antimicrobially active iodopropynyloxyethanol carbamate compound, components a and b being in a weight ratio of a: b in the range from 300: 1 to 0.05: 1.
Dabei kommen als antimikrobiell wirksame Substanzen Chloracetamide in Betracht, die der Formel I Chloracetamides which have the formula I are suitable as antimicrobial substances
R1 = R2 = H; R1 = CH3 -, R2 = lineare C5H11-bis C12H23-Alkylreste; R1 = H, R2 =
R 1 = R 2 = H; R 1 = CH 3 -, R 2 = linear C 5 H 11 to C 12 H 23 alkyl radicals; R 1 = H, R 2 =
sein können. Diese Verbindungen können in den erfindungsgemäßen Gemischen als chemische Individuen oder als Gemische enthalten sein. Beispiele für derartige antimikrobiell wirksame Verbindungen sind N-(4-Brom-2-methylphenyl)-2-chloracetamid, gemäß EP 137 729 A2 oder N-Methyl-N-heptylchloracetamid. could be. These compounds can be contained in the mixtures according to the invention as chemical individuals or as mixtures. Examples of such antimicrobial compounds are N- (4-bromo-2-methylphenyl) -2-chloroacetamide, according to EP 137 729 A2 or N-methyl-N-heptylchloroacetamide.
Als antimikrobiell wirksame Jodpropinyloxy-ethanol-carbamatverbindungen eignen sich insbesondere 2-(3-Iod-2-propinyloxy)-ethanol-carbamate der allgemeinen Formel (II) Suitable antimicrobial iodopropynyloxyethanol carbamate compounds are, in particular, 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II)
Beispiele für lineare oder verzweigte Alkylreste oder Alkenylreste mit 1 bis 6 Kohlenstoffatomen, für die R1 und R2 stehen, sind der Methyl-, Ethyl-, Propyl-, Isopropyl-, n-Butyl-, Isobutyl-, sec.-Butyl-, tert.-Butyl-, Pentyl-, der Hexylrest und deren verzweigte Isomere wie der Vinyl-, Allyl-, Propenyl-, Butenyl-, Pentenyl- und Hexenylreste sowie die entsprechenden Isomeren der genannten Alkenyle mit 4, 5 und 6 Kohlenstoffatomen. Beispiele für cyclische Alkylreste mit 5 bis 7 Kohlenstoffatomen, für die Rl und R2 stehen, sind der Cyclopentan-, Cyclohexan- und der Cycloheptanrest. Bevorzugt werden Verbindungen der Formel (II), in denen beide Substituenten R1 und R2 gleichzeitig Wasserstoff oder gleichzeitig Methylreste sind, sowie solche, in denen bei R* und R2 ein Substituent Wasserstoff ist, während der andere einen Methylrest darstellt. Examples of linear or branched alkyl radicals or alkenyl radicals with 1 to 6 carbon atoms, for which R 1 and R 2 stand, 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 with 4, 5 and 6 carbon atoms. Examples of cyclic alkyl radicals having 5 to 7 carbon atoms, for which R 1 and R 2 stand, are the cyclopentane, cyclohexane and cycloheptane radicals. Compounds of the formula (II) in which both substituents R 1 and R 2 are simultaneously hydrogen or simultaneously methyl radicals are preferred, and compounds in which one of R * and R 2 is hydrogen while the other represents a methyl radical.
Beispiele für Alkylreste mit 1 bis 4 Kohlenstoffatomen, für die R3, R4, R5 und R6 stehen, sind der Methyl-, Ethyl-, Propyl-, Isopropyl- und der n-Butylrest, Isobutyl, sec.-Butyl und tert.-Butyl, wobei Methyl bevorzugt wird. Examples of alkyl radicals with 1 to 4 carbon atoms, which R 3 , R 4 , R 5 and R 6 represent, are the methyl, ethyl, propyl, isopropyl and n-butyl radical, isobutyl, sec-butyl and tert-butyl, with methyl being preferred.
Beispiele für Arylreste, für die R3, R4, R5 und R6 stehen, sind der Phenyl- und der Naphthylrest. Examples of aryl radicals represented by R 3 , R 4 , R 5 and R 6 are the phenyl and the naphthyl radical.
Bevorzugt sind Verbindungen der allgemeinen Formel (II), in denen von den Resten R1 bis R6 mindestens 4 Reste Wasserstoff bedeuten.
Beispiele für lineare und verzweigte Alkylreste mit 1 bis 12 Kohlenstoffatomen, für die R? steht, sind der Methyl-, Ethyl-, Propyl-, Isopropyl-, n-Butyl-, Isobutyl-, sec.-Butyl-, tert.-Butyl-, Pentyl-, Hexyl-, Heptyl-, Octyl-, Nonyl-, Decyl-, Undecyl- und der Dodecylrest sowie die verzweigten Isomeren der Alkyle mit 5 bis 12 Kohlenstoffatomen. Compounds of the general formula (II) in which at least 4 radicals of the radicals R 1 to R 6 are hydrogen are preferred. Examples of linear and branched alkyl radicals with 1 to 12 carbon atoms for which R? is 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.
Beispiele für cyclische Alkylreste mit 4 bis 8 Kohlenstoffatomen, für die R7 steht, sind der Cyclobutyl-, Cyclopentyl-, Cyclohexyl-, Cycloheptyl- und der Cyclooctylrest. Examples of cyclic alkyl radicals with 4 to 8 carbon atoms, for which R7 stands, are the cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl radical.
Beispiele für Aryl und substituiertes Aryl, für die R7 steht, sind der Phenyl-, Naphthyl-, Tolyl-, Chlorphenyl-, Bromphenyl-, Fluorphenyl-, Dichlorphenyl- und der Trichlorphenylrest. Examples of aryl and substituted aryl which R 7 represents are the phenyl, naphthyl, tolyl, chlorophenyl, bromophenyl, fluorophenyl, dichlorophenyl and the trichlorophenyl radical.
Beispiele für Aralkyl und Arylsulfonyl, für die R7 steht, sind der Benzyl- und der p-Toluolsulfonylrest. Examples of aralkyl and arylsulfonyl for which R 7 stands are the benzyl and p-toluenesulfonyl radicals.
Bevorzugt werden Verbindungen, in denen R7 ein niederer Alkylrest mit 1 bis 4 Kohlenstoffatomen, sowie ein Arylrest oder mit Chlor oder Brom substituierter Arylrest ist. Compounds in which R 7 is a lower alkyl radical having 1 to 4 carbon atoms and an aryl radical or aryl radical substituted by chlorine or bromine are preferred.
Beispiele für besonders bevorzugte Verbindungen sind solche, in denen R7 ein Propyl-, Butyl- oder Phenylrest ist. Examples of particularly preferred compounds are those in which R 7 is a propyl, butyl or phenyl radical.
Die N-substituierten 2-(3-Iod-2-propinyloxy)-ethanol-carbamate der allgemeinen Formel (II) werden nach an sich bekannten Verfahren (Houben-Weyl, Methoden der Org. Chemie, Bd. 8, S. 141 - 144 (1952)) durch Umsetzung äquimolarer Mengen der Alkohole mit geeigneten, z.B. im Handel erhältlichen Isocyanaten synthetisiert, wie beispielsweise in der DE 32 16 894 Al und in der DE 32 16 895 Al beschrieben ist. The N-substituted 2- (3-iodo-2-propynyloxy) ethanol carbamates of the general formula (II) are prepared by methods 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 are synthesized, as described, for example, in DE 32 16 894 Al and in DE 32 16 895 Al.
Bei der Bestimmung der mikrobistatischen Wirkung an verschiedenen Bakterien- und Pilzkulturen konnten mit solchen Gemischen deutlich synergistische Wirkungen beobachtet werden.
Gemäß einer bevorzugten Ausführungsform der vorliegenden Erfindung wir das Gewichtsverhältnis der Komponenten a und b im Bereich von 100 : 1 bis 0,1 : 1 eingestellt. When determining the microbistatic effect on different bacterial and fungal cultures, it was possible to observe clearly synergistic effects with such mixtures. According to a preferred embodiment of the present invention, the weight ratio of components a and b is set in the range from 100: 1 to 0.1: 1.
Zur Herstellung gebrauchsfertiger antimikrobieller Mittel können die erfindungsgemäßen antimikrobiell wirksamen Gemische in Form von pulverförmigen oder lösungsmittelhaltigen Konzentraten bereitgestellt werden, in denen die Gesamtkonzentration der Komponenten a und b von etwa 0,5 bis zu 100, vorzugsweise von 10 bis zu 90 Gew.-% ausmachen kann. Geeignete gebrauchsfertige Mittel haben insbesondere eine Konzentration von 10 bis 50 Gew.-% der erfindungsgemäßen Mischung von a und b. To prepare ready-to-use antimicrobial agents, 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 10 to 90,% by weight can. Suitable ready-to-use agents have in particular a concentration of 10 to 50% by weight of the mixture of a and b according to the invention.
In der Mehrzahl der Fälle enthalten die für die praktische Anwendung bestimmten Gemische insgesamt noch 0 bis etwa 99, vorzugsweise 90 bis 10 Gew.-% weitere üblicherweise verwendete Bestandteile, die je nach der vorgesehenen Anwendungsform und dem Anwendungszweck ausgewählt werden. Für flüssige Zubereitungen beispielsweise kommen als Lösungsmittel mit Wasser mischbare organische Lösungsmittel in Betracht, beispielsweise Ethanol, Isopropanol und Ethylenglykol, Propylenglykol, Ethylethylenglykol, Propylpropylenglykol sowie mit Wasser nicht mischbare Lösungsmittel wie beispielsweise Testbenzin, Benzol, Toluol, Essigsäureethylester oder Dimethylenchlorid. In the majority of cases, the mixtures intended for practical use still contain a total of 0 to about 99, preferably 90 to 10% by weight of further commonly used constituents which are selected depending on the intended form of use and the intended use. For liquid preparations, for example, 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 dimethylene chloride.
Wenn neben der antimikrobiellen Wirkung eine zusätzliche Reinigungswirkung erwünscht ist, können die erfindungsgemäßen Gemische auch noch Tenside, insbesondere nichtionische Tenside enthalten. Beispiele für geeignete Tenside sind Anlagerungsprodukte von 4 bis 40, vorzugsweise 4 bis 20 Mol Ethy lenoxid an ein Mol Fettalkohol, Alkylcyclohexanol, Alkylphenol, Fettsäure, Fettsäureamid oder Alkansulfonamid. Von besonderem Interesse sind Anlagerungsprodukte von 5 bis 16 Mol Ethylenoxid an Kokos- oder Talgfettalkohole, an Oleylalkohol, ein Gemisch aus Oleylalkohol und Cetylalkohol sowie an Mono-, Di- oder Trialkylphenole und an Monoalkylcyclohexanole mit 6 bis 14 Kohlenstoffatomen in den Alkylresten. Auch gemischte Anlagerungsprodukte von Ethylenoxid und Propylenoxid an die genannten Verbindungen mit einem aktiven Wasserstoffatom kommen in Betracht. Die genannten Alkoxylierungsprodukte können auch endgruppenverschlossen sein, beispielsweise
durch Ether- oder Acetalgruppen. Die Tensidmenge kann etwa 0,001 bis etwa 2, vorzugsweise etwa 0,01 bis 0,15 Gew.-%, bezogen auf das konfektionierte Mittel, betragen. If, in addition to the antimicrobial action, an additional cleaning action is desired, the mixtures according to the invention can also contain surfactants, in particular nonionic surfactants. Examples of suitable surfactants are adducts of 4 to 40, preferably 4 to 20, moles of ethylene oxide with one mole of fatty alcohol, alkylcyclohexanol, alkylphenol, fatty acid, fatty acid amide or alkanesulfonamide. Addition products of 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 and with mono-, di- or trialkylphenols and with monoalkylcyclohexanols with 6 to 14 carbon atoms in the alkyl radicals 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. The amount of surfactant can be about 0.001 to about 2, preferably about 0.01 to 0.15% by weight, based on the compound.
In den erfindungsgemäßen Gemischen können ferner Gerüstsubstanzen vorhanden sein; als solche eignen sich beispielsweise Alkalisalze der Glukonsäure, insbesondere Natriumglukonat, die Alkalisalze der Nitrilotriessigsäure, Ethylendiamintetraessigsäure, Hydroxyethandiphosphonsäure, Phosphonobutantricarbonsäure, Milchsäure, Zitronensäure oder Weinsäure. Weiterhin kommen als Gerüstsubstanzen die wasserlöslichen Salze höhermolekularer Polycarbonsäuren in Betracht, etwa Polymerisate der Maleinsäure, Itakonsäure, Fumarsäure und Zitraconsäure. Auch Mischpolymerisate dieser Säuren untereinander oder mit anderen polymerisierbaren Monomeren, wie z.B. Ethylen, Propylen, Acrylsäure, Vinylacetat, Isobutylen, Acrylamid und Styrol sind brauchbar. Die Mengen der Gerüstsubstanzen können etwa 0,01 bis 2, vorzugsweise 0,02 bis 1,0 Gew.-%, bezogen auf das konfektionierte Mittel, betragen. Builders may also be present in the mixtures according to the invention; Suitable as such are, for example, alkali metal salts of gluconic acid, in particular sodium gluconate, the alkali metal salts of nitrilotriacetic acid, ethylenediaminetetraacetic acid, hydroxyethane diphosphonic acid, phosphonobutane tricarboxylic acid, lactic acid, citric acid or tartaric acid. The water-soluble salts of higher molecular weight polycarboxylic acids, for example polymers of maleic acid, itaconic acid, fumaric acid and citraconic acid, are also suitable as builders. 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. The amounts of the builder substances can be about 0.01 to 2, preferably 0.02 to 1.0,% by weight, based on the compound.
In die erfindungsgemäßen Gemische können auch Reinigungsverstärker wie Fettsäuremono- und -diethanolamide, beispielsweise Kokosfettsäuremonoethanolamid und Kokosfettsäurediethanolamid, und Anlagerungsprodukte von bis zu 4 Mol Ethylenoxid oder Propylenoxid an Fettalkohole mit 8 bis 12 Kohlenstoffatomen sowie freie Fettalkohole mit 8 bis 12 Kohlenstoffatomen sowie Reinigungsverstärker auf Cellulosebasis eingearbeitet werden. Die Mengen an Reinigungsverstärkern können etwa 0,001 bis 0,02, vorzugsweise etwa 0,005 bis 0,01 Gew.-%, bezogen auf das konfektionierte Mittel, betragen. Cleaning enhancers such as fatty acid mono- and diethanolamides, for example coconut fatty acid monoethanolamide and coconut fatty acid diethanolamide, and addition products of up to 4 moles of ethylene oxide or propylene oxide with fatty alcohols with 8 to 12 carbon atoms and free fatty alcohols with 8 to 12 carbon atoms as well as cleaning enhancers based on cellulose can also be incorporated into the mixtures according to the invention . The amounts of cleaning boosters can be about 0.001 to 0.02, preferably about 0.005 to 0.01% by weight, based on the compound.
Darüber hinaus kann es für weitere Anwendungsbereiche vorteilhaft sein, wenn die erfindungsgemäßen Gemische zusätzlich zu der erfindungsgemäßen Kombination aus Chloracetamidverbindungen und Jodpropinyloxy-ethanol-carbamatverbindungen weitere antimikrobiell wirksame Substanzen enthalten. In die erfindungsgemäßen Mischungen können auch Insekticide wie z.B. Pyrethrofde (Permethrin, Cypermethrin, Decamethrin und Fenvalerate) und/ oder Lindan, Endosulfan, Dieldrin eingearbeitet werden. Die Mengen dieser Zusätze sollen jedoch unter denen der beiden erfindungsgemäß verwendeten Bestandteile liegen.
Die Mengen der der möglichen zur Konfektionierung der erfindungsgemäßen Mittel benutzten Bestandteile richten sich im allgemeinen nach Handelsund Preisvorgaben und sind im Prinzip nicht von erfinderischer Bedeutung. In addition, it can be advantageous for other areas of application if the mixtures according to the invention contain, in addition to the combination of chloroacetamide compounds and iodopropynyloxyethanol carbamate compounds according to the invention, further antimicrobial substances. Insecticides such as pyrethrofde (permethrin, cypermethrin, decamethrin and fenvalerate) and / or lindane, endosulfan, dieldrin can also be incorporated into the mixtures according to the invention. However, the amounts of these additives are said to be lower than those of the two components used according to the invention. The amounts of the possible components used to assemble the agents according to the invention are generally based on commercial and price specifications and are in principle not of inventive importance.
Für die Herstellung gebrauchsfertiger Konservierungsmittel können neben flüssigen Konzentraten auch feste Produkte, vorzugsweise in Pulver- oder Granulatform bereitgestellt werden, die die erfindungsgemäßen antimikrobiell wirksamen Gemische enthalten. In addition to liquid concentrates, solid products, preferably in powder or granule form, which contain the antimicrobial mixtures according to the invention can also be provided for the production of ready-to-use preservatives.
Die erfindungsgemäßen antimikrobiell synergistisch wirksamen Gemische können als Desinfektions- und Konservierungsmittel auf vielen Gebieten zum Einsatz gelangen, beispielsweise in Haushalten und im Gewerbe wie z.B. Krankenhäusern, Schulen, Badeanstalten, öffentlichen Verkehrsmitteln, gewerblichen Betrieben und Industrieanlagen bei der Antischimmelausrüstung von Teppichböden, Wandverkleidungen und Dichtungsmassen. Ferner können die synergistischen Gemische zum Konservieren von Pflanzenvermehrungsmaterial, insbesondere von Samen und Blumenzwiebeln eingesetzt werden. Weiterhin können die erfindungsgemäßen Gemische bei der Konservierung noch zu verarbeitender technischer Produkte wie Lasuren, Lack- und Dispersions- und Emulsionsfarben, Klebstoffen und Kleistern, Bohr- und Schneidölen oder Produkten der papier-, pappe- oder lederverarbeitenden Industrie sowie zur Konservierung von Industrie- und Brauchwasser Anwendung finden. Schließlich können die erfindungsgemäßen Gemische auch zum fertigen Materialschutz eingesetzt werden, beispielsweise zur Antischimmelausrüstung von Putzen, Anstrichen, Kunststoffen, Boden- bzw. Wandbelägen aus Textilien, Papier, Kunststoffen, Leder, Kork oder zum Imprägnieren von Holz. Hier können u.a. Kisten, wie sie in der gewerblichen Pilzzucht verwendet werden, wirkungsvoll gegen den Befall durch das Kulturmyzel ausgerüstet werden. Die Applikation kann etwa durch Sprühen, Pinseln, Streichen, Rakeln, Tauchen oder Druck- oder Vakuumimprägnierung erfolgen. Die Anwendungskonzentrationen liegen im allgemeinen bei etwa 0,001 bis 5, vorzugsweise bei etwa 0,01 bis 2 Gew.-% Aktivsubstanzgemisch.
B e i s p i e l e 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 trade, such as hospitals, schools, bathing establishments, public transport, commercial plants and industrial plants in the anti-mold finishing of carpets, wall coverings and sealing compounds. Furthermore, the synergistic mixtures can be used to preserve plant propagation material, in particular seeds and flower bulbs. Furthermore, the mixtures according to the invention can be used in the preservation of technical products still to be processed, such as glazes, lacquer and dispersion and emulsion paints, adhesives and pastes, drilling and cutting oils or products from the paper, cardboard or leather-processing industry, and for the preservation of industrial and Find domestic water application. Finally, 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. Here, among other things, 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. The application concentrations are generally about 0.001 to 5, preferably about 0.01 to 2,% by weight of active substance mixture. Examples
Beispiel 1 example 1
Als antimikrobiell wirksame Chloracetamidverbindungen wurde N-(4-Brom-2- methylenphenyl)-2-chloracetamid (Produkt A) eingesetzt. Als antimikrobiell wirksame Jodpropinyloxy-ethanol-carbamate (Produkt B) kamen folgende Verbindungen der Formel (III) zum Einsatz: The antimicrobial chloroacetamide compounds used were N- (4-bromo-2-methylenephenyl) -2-chloroacetamide (product A). The following compounds of the formula (III) were used as antimicrobial iodopropynyloxyethanol carbamates (product B):
I-C≡C-CH2-O-CH2CH2-O-CONH-C6H5 (III) IC≡C-CH 2 -O-CH 2 CH 2 -O-CONH-C 6 H 5 (III)
Produkt A wurde mit Produkt B zu folgenden erfindungsgemäßen Gemischen kombiniert (GT = Gewichtsteile): Product A was combined with product B to the following mixtures according to the invention (GT = parts by weight):
Gemisch AB 1 Mixture AB 1
0,15 GT Produkt A 0.15 GT product A
1 GT Produkt B 1 GT product B
Gemisch AB 2 Mixture AB 2
0,19 GT Produkt A 0.19 GT product A
1 GT Produkt B 1 GT product B
Gemisch AB 3 Mixture AB 3
1 GT Produkt A 1 GT product A
1 GT Produkt B 1 GT product B
Gemisch AB 4 Mixture AB 4
0,35 GT Produkt A 0.35 GT product A
1 GT Produkt B 1 GT product B
Gemisch AB 5 Mixture AB 5
2 GT Produkt A 2 GT product A
1 GT Produkt B 1 GT product B
Die mikrobistatische Wirksamkeit der erfindungsgemäßen Gemische AB 1 bis AB 5 im Vergleich zu den Einzelkomponenten (Produkte A und B) wurde gegenüber folgenden Testkeimsuspensionen bestimmt:
1. Staphylococcus aureus 2 × 109 Keime/ml The microbistatic activity of the mixtures AB 1 to AB 5 according to the invention in comparison with the individual components (products A and B) was determined with respect to the following test germ suspensions: 1. Staphylococcus aureus 2 × 10 9 germs / ml
2. Candida albicans 1 × 108 Keime/ml 2. Candida albicans 1 × 10 8 germs / ml
3. Aspergillus niger 4 × 107 Keime/ml 3. Aspergillus niger 4 × 10 7 germs / ml
4. Penicillium camerunense 5 × 107 Keime/ml 4. Penicillium camerunense 5 × 10 7 germs / ml
5. Trichoderma viride 6 × 107 Keime/ml 5. Trichoderma viride 6 × 10 7 germs / ml
Die Hemmkonzentrationen der zu untersuchenden Produkte wurden in Anlehnun an die Richtlinien für die Prüfung und Bewertung chemischer Desinfektionsverfahren, Kapitel 2.1, abgedruckt in Zbl. Bakt. Hyg., I. Abt. Orig. 172, 536-537 (1981), ermittelt. Die Substanzgemische AB 1 bis AB 5 und di Einzelkomponenten A und B wurden zu Stammlösungen in Dimethylformamid ge löst, aus denen durch Zusatz von Würzebouillon im Volumenverhältnis 1 : 50 die entsprechenden Verdünnungsreihen hergestellt wurden. The inhibitory concentrations of the products to be tested were based on the guidelines for the testing and evaluation of chemical disinfection processes, chapter 2.1, printed in Zbl. Bakt. Hyg., I. Dept. Orig. 172, 536-537 (1981). The substance mixtures AB 1 to AB 5 and di individual components A and B were dissolved in stock solutions in dimethylformamide, from which the corresponding dilution series were prepared by adding wort broth in a volume ratio of 1:50.
Die gefundenen Ergebnisse sind in der nachstehenden Tabelle I wiederge geben: The results found are shown in Table I below:
TA B E L L E I TA B E L L E I
Hemmkonzentrationen der Gemische AB 1 bis AB 5 in ppm Inhibitory concentrations of the mixtures AB 1 to AB 5 in ppm
im Vergleich zu den Einzelkomponenten A und B compared to the individual components A and B
Produkt T e s t k e i m Product T e s t k e i m
1 2 3 4 5 1 2 3 4 5
AB 1 7 + 45 - - - -FROM 1 7 + 45 - - - -
AB 2 - 1 , 5 + 8 - - -FROM 2 - 1, 5 + 8 - - -
AB 3 - - 3 + 3 - -FROM 3 - - 3 + 3 - -
AB 4 - - - 0,7 + 2 -FROM 4 - - - 0.7 + 2 -
AB 5 - - - - 2 + 1 AB 5 - - - - 2 + 1
A 70 7 15 1 ,5 7 A 70 7 15 1, 5 7
B 125 15 20 7 7 B 125 15 20 7 7
In der Tabel le wurden für die Hemmkonzentrationen der erfindungsgemäßenIn the table le for the inhibitory concentrations of the invention
Gemische AB 1 bis AB 5 jewei ls die Mengen der Einzelkomponenten aufgenom
men, die in den oben angegebenen Gewichtsverhältnissen eingesetzt wurden. Mixtures AB 1 to AB 5 each contain the quantities of the individual components men that were used in the weight ratios indicated above.
Beim Einsatz der erfindungsgemäßen Gemische AB 1 bis AB 5 konnten praktisch durchweg synergistische Effekte beobachtet werden. When using the mixtures AB 1 to AB 5 according to the invention, synergistic effects were observed practically throughout.
Beispiel 2 Example 2
Als antimikrobiell wirksame Chloracetamidverbindung wurde Chloracetamid (Produkt C) eingesetzt. Als antimikrobiell wirksame Jodpropinyloxy-ethanol-carbamatverbindung kam Produkt B zum Einsatz. Chloroacetamide (Product C) was used as the antimicrobial chloroacetamide compound. Product B was used as the antimicrobial iodopropynyloxyethanol carbamate compound.
Produkt C wurde mit Produkt B zu folgenden erfindungsgemäßen Gemischen kombiniert: Product C was combined with product B to the following mixtures according to the invention:
Gemisch CB 1 Mixture CB 1
100 GT Produkt C 100 GT product C
1 GT Produkt B 1 GT product B
Gemisch CB 2 Mixture CB 2
66 GT Produkt C 66 GT product C
1 GT Produkt B 1 GT product B
Die mikrobistatische Wirksamkeit der erfindungsgemäßen Gemische (Produkte CB 1 und CB 2) im Vergleich zu den Einzelkomponenten (Produkte C und B) wurde gegenüber den im Beispiel 1 beschriebenen Testkeimsuspensionen bestimmt. Die Hemmkonzentrationen wurden analog Beispiel 1 ermittelt. Die gefundenen Ergebnisse sind in der Tabelle II zusammengefaßt.
The microbistatic activity of the mixtures according to the invention (products CB 1 and CB 2) in comparison to the individual components (products C and B) was determined compared to the test germ suspensions described in Example 1. The inhibitory concentrations were determined analogously to Example 1. The results found are summarized in Table II.
T A B E L L E I I Hemmkonzentrationen der Gemische CB 1 und CB 2 in ppm im Vergleich zu den Einzelkomponenten C und B T A B E L L E I I Inhibitory concentrations of the mixtures CB 1 and CB 2 in ppm compared to the individual components C and B
Produkt T e s t k e i m Product T e s t k e i m
2 3 4 2 3 4
CB 1 600+6 - -CB 1 600 + 6 - -
CB 2 - 130+2 100+ 1,5 CB 2 - 130 + 2 100+ 1.5
C 1500 800 500 C 1500 800 500
B 15 8 7 B 15 8 7
Beim Einsatz der erfindungsgemäßen Gemische CB 1 und CB 2 gegen die Testkeime 2 bis 4 konnten praktisch durchweg synergistische Effekte beobachtet werden. When the mixtures CB 1 and CB 2 according to the invention were used against the test germs 2 to 4, synergistic effects were observed practically without exception.
Als antimikrobiell wirksame Chloracetamidverbindung wurde N-Methyl-N-heptylchloracetamid (Produkt D) eingesetzt. Als antimikrobiell wirksame Jodpropinyloxy-ethanol-carbamatverbindung kam Produkt B zu Einsatz. N-Methyl-N-heptylchloroacetamide (product D) was used as the antimicrobial chloracetamide compound. Product B was used as an antimicrobial iodopropynyloxyethanol carbamate compound.
Produkt D wurde mit den Produkten zu folgenden erfindungsgemäßen Gemischen kombiniert: Product D was combined with the products to give the following mixtures according to the invention:
Gemisch DB 1 Mixture DB 1
1 GT Produkt D 1 GT product D
1 GT Produkt B 1 GT product B
Gemisch DB 2 Mixture DB 2
3 GT Produkt D 3 GT product D
1 GT Produkt B 1 GT product B
Gemisch DB 3 Mixture DB 3
5 GT Produkt D 5 GT product D
1 GT Produkt B
Die mikrobistatische Wirksamkeit der erfindungemäßen Gemische (Produkte DB 1 bis DB 3) im Vergleich zu den Einzelkomponenten (Produkte D und B) wurde gegenüber den im Beispiel 1 beschriebenen Testkeimsuspensionen bestimmt. Die Hemmkonzentrationen wurden analog Beispiel 1 ermittelt. Die gefundenen Ergebnisse sind in der Tabelle III zusammengefaßt: 1 GT product B The microbistatic activity of the mixtures according to the invention (products DB 1 to DB 3) in comparison to the individual components (products D and B) was determined compared to the test germ suspensions described in example 1. The inhibitory concentrations were determined analogously to Example 1. The results found are summarized in Table III:
T A B EL L E III T A B EL L E III
Hemmkonzentrationen der Gemische DB 1 bis DB 3 in ppm im Vergleich zu den Eiπzelkomponenten D und B Inhibitory concentrations of the mixtures DB 1 to DB 3 in ppm compared to the individual components D and B
Produkt T e s t k e i m Product T e s t k e i m
1 2 3 4 1 2 3 4
DB 1 45 + 45 - - -DB 1 45 + 45 - - -
DB 2 - 24 + 8 - -DB 2 - 24 + 8 - -
DB 3 - - 10 + 2 10 + 2 DB 3 - - 10 + 2 10 + 2
D 200 75 75 50 D 200 75 75 50
B 125 15 8 15 B 125 15 8 15
Beim Einsatz der erfindungsgemäßen Gemische DB 1 bis DB 3 gegen die Testkeime 1 bis 4 konnten praktisch durchweg synergistische Effekte beobachtet werden.
When using the mixtures DB 1 to DB 3 according to the invention against the test germs 1 to 4, synergistic effects were observed practically without exception.
Claims
1. Antimikrobiell wirksame Gemische enthaltend 1. Containing antimicrobial mixtures
a) mindestens ein antimikrobiell wirksames Chloracetamid bzw. a) at least one antimicrobial chloracetamide or
substituiertes Chloracetamid und substituted chloroacetamide and
b) mindestens eine antimikrobiell wirksame Jodpropinyloxy-ethanol- carbamatverbindung, b) at least one antimicrobially active iodopropynyloxyethanol carbamate compound,
wobei die Komponenten a und b im Gewichtsverhältnis von a : b im the components a and b in the weight ratio of a: b in
Bereich von 300 : 1 bis 0,05 : 1 vorliegen. Range from 300: 1 to 0.05: 1.
2. Antimikrobiell wirksame Gemische nach Anspruch 1, dadurch gekennzeichnet, daß die Komponenten a und b im Gewichtsverhältnis von a : b im Bereich von 100 : 1 bis 0,1 : 1 vorliegen. 2. Antimicrobial mixtures according to claim 1, characterized in that components a and b are present in the weight ratio of a: b in the range from 100: 1 to 0.1: 1.
3. Antimikrobiell wirksame Gemische nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß sie als antimikrobiell wirksame Chloracetamidverbindungen Substanzen enthalten, die der Formel I 3. Antimicrobially active mixtures according to claim 1 or 2, characterized in that they contain, as antimicrobially active chloroacetamide compounds, substances which have the formula I.
R1 = R2 = H oder R 1 = R 2 = H or
R1 = CH3; R2 = lineare C5 H11 bis C12 H25-Alkylreste, vorzugsweise C7 H15 oder R 1 = CH 3 ; R 2 = linear C 5 H 11 to C 12 H 25 alkyl radicals, preferably C 7 H 15 or
bedeuten. 
mean.
4. Antimikrobiell wirksame Gemische nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß sie als antimikrobiell wirksame Chloracetamidverbindungen Chloracetamid, N-(C4-Brom-2-methylenphenyl)-2-chloracetamid, N-Methyl-N-heptylchloracetamid oder Gemische dieser Verbindungen enthalten. 4. Antimicrobially active mixtures according to claims 1 to 3, characterized in that they are antimicrobially active chloroacetamide compounds chloroacetamide, N- (C4-bromo-2-methylenephenyl) -2-chloroacetamide, N-methyl-N-heptylchloroacetamide or mixtures of these compounds contain.
5. Antimikrobiell wirksame Gemische nach den Ansprüchen 1 bis 4, dadurch gekennzeichnet, daß sie als antimikrobiell wirksame Jodpropinyloxy- ethanol-carbamatverbindungen Substanzen enthalten, die der Formel (II) 5. Antimicrobially active mixtures according to claims 1 to 4, characterized in that they contain as antimicrobial iodopropynyloxyethanol carbamate compounds substances which have the formula (II)
in der R1 und R2 gleich oder verschieden sind und Wasserstoff, lineare oder verzweigte Alkyl- oder Alkenylreste mit 1 bis 6 Kohlenstoffatomen oder cyclische Alkylreste mit 5 bis 7 Kohlenstoffatomen oder R1 und R2 zusammengenommen -(CH2)n bedeuten, wobei n 4 bis 6 ist, R3, R4, R5 und R6, die gleich oder verschieden sein können, Wasserstoff, Alkylreste mit 1 bis 4 Kohlenstoffatomen, Arylreste oder CCl3 bedeuten oder R3und R5 oder R4 und R6 zusammengenommen -(CH2)nbedeuten, wobei n 3 bis 5 ist, und R7 Wasserstoff, lineare oder verzweigte Alkylreste mit 1 bis 12 Kohlenstoffatomen oder cyclische Alkylreste mit 4 bis 8 Kohlenstoffatomen, Arylreste, substituierte Arylreste, Aralkylreste oder Arylsulfonylreste bedeutet. in which R 1 and R 2 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 2 taken together - (CH 2 ) n , where n is 4 to 6, R 3 , R 4 , R5 and R 6 , which may be the same or different, denote hydrogen, alkyl radicals having 1 to 4 carbon atoms, aryl radicals or CCl 3 or R 3 and R 5 or R 4 and R 6 taken together - mean (CH 2 ) 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, aralkyl radicals or arylsulfonyl radicals.
6. Antimikrobiell wirksame Gemische nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß sie als antimikrobiell wirksame Jodpropinyloxy- ethanol-carbonatverbindung eine Substanz der Formel (III) 6. Antimicrobially active mixtures according to claims 1 to 5, characterized in that they are a substance of the formula (III) as iodine-propyloxy-ethanol-carbonate compound having antimicrobial activity.
I - C≡ C - CH2 - O - CH2 CH2 - O - CONH - C6 H5 enthalten. I - C≡ C - CH 2 - O - CH 2 CH 2 - O - CONH - C 6 H 5 included.
7. Antimikrobiell wirksame Gemische nach den Ansprüchen 1 bis 6, dadurch gekennzeichnet, daß sie als pulverförmige oder lösungsmittelhaltige Konzentrate mit einer Gesamtkonzentration der Komponenten a und b von insgesamt etwa 0,5 bis zu 100, vorzugsweise etwa 10 bis 90 Gew.-%, bezogen auf das gesamte Konzentrat, vorliegen. 7. antimicrobially active mixtures according to claims 1 to 6, characterized in that they as powdery or solvent-containing concentrates with a total concentration of components a and b of a total of about 0.5 to 100, preferably about 10 to 90 wt .-%, based on the total concentrate.
8. Verwendung der antimikrobiell wirksamen Gemische nach den Ansprüchen 1 bis 7 für die Konservierung von Lasuren, Lack- und Dispersionsfarben und -lacken, Emulsiσnsfarben und -lacken, Klebstoffen und Kleistern, Bohr- und Schneidölen in Haushalten und Gewerbebetrieben. 8. Use of the antimicrobially active mixtures according to claims 1 to 7 for the preservation of glazes, lacquer and dispersion paints and varnishes, emulsion paints and varnishes, adhesives and paste, drilling and cutting oils in households and businesses.
9. Verwendung der antimikrobiell wirksamen Gemische nach den Ansprüchen 1 bis 7 für die Konservierung in der papier-, pappe- und lederverarbeitenden Industrie. 9. Use of the antimicrobial mixtures according to claims 1 to 7 for preservation in the paper, cardboard and leather processing industries.
10. Verwendung der antimikrobiell wirksamen Gemische nach den Ansprüchen 1 bis 7 zum Konservieren von Industrie- und Brauchwasser. 10. Use of the antimicrobial mixtures according to claims 1 to 7 for the preservation of industrial and industrial water.
11. Verwendung der antimikrobiell wirksamen Gemische nach den Ansprüchen 1 bis 7 zum Materialschutz, wie zur Antischimmelausrüstung von Putzen, Anstrichen, Kunststoffen, Boden- bzw. Wandbelägen aus Textilien, Papier, Kunststoffen, Leder, Kork und insbesondere zum Imprägnieren von Holz. 11. Use of the antimicrobially active mixtures according to claims 1 to 7 for material protection, such as for anti-mold finishing of plasters, paints, plastics, floor and wall coverings made of textiles, paper, plastics, leather, cork and in particular for impregnating wood.
12. Verwendung der antimikrobiell wirksamen Gemische und den Ansprüchen 1 bis 7 mit Aktivsubstanzgemischkonzentrationen von etwa 0,001 bis 5, vorzugsweise etwa 0,01 bis 2 Gew.-%. 12. Use of the antimicrobially active mixtures and claims 1 to 7 with active substance mixture concentrations of about 0.001 to 5, preferably about 0.01 to 2 wt .-%.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5506585A JPH07500097A (en) | 1991-10-02 | 1992-09-23 | antibacterial mixture |
| EP92920153A EP0606290A1 (en) | 1991-10-02 | 1992-09-23 | Antimicrobial-agent mixtures |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914132772 DE4132772A1 (en) | 1991-10-02 | 1991-10-02 | ANTIMICROBIAL ACTIVE MIXTURES |
| DEP4132772.1 | 1991-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993006729A1 true WO1993006729A1 (en) | 1993-04-15 |
Family
ID=6441965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1992/002200 WO1993006729A1 (en) | 1991-10-02 | 1992-09-23 | Antimicrobial-agent mixtures |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0606290A1 (en) |
| JP (1) | JPH07500097A (en) |
| AU (1) | AU2640692A (en) |
| DE (1) | DE4132772A1 (en) |
| WO (1) | WO1993006729A1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093962A1 (en) * | 1982-05-06 | 1983-11-16 | Henkel Kommanditgesellschaft auf Aktien | 2-(3-Iodo-2-propynyloxy)-ethanol carbamates, preparation and use thereof as a microbicidal substance |
| EP0299191A1 (en) * | 1987-06-09 | 1989-01-18 | Henkel Kommanditgesellschaft auf Aktien | Mixture of fungicidally active agents |
-
1991
- 1991-10-02 DE DE19914132772 patent/DE4132772A1/en not_active Withdrawn
-
1992
- 1992-09-23 WO PCT/EP1992/002200 patent/WO1993006729A1/en not_active Application Discontinuation
- 1992-09-23 AU AU26406/92A patent/AU2640692A/en not_active Abandoned
- 1992-09-23 JP JP5506585A patent/JPH07500097A/en active Pending
- 1992-09-23 EP EP92920153A patent/EP0606290A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0093962A1 (en) * | 1982-05-06 | 1983-11-16 | Henkel Kommanditgesellschaft auf Aktien | 2-(3-Iodo-2-propynyloxy)-ethanol carbamates, preparation and use thereof as a microbicidal substance |
| EP0299191A1 (en) * | 1987-06-09 | 1989-01-18 | Henkel Kommanditgesellschaft auf Aktien | Mixture of fungicidally active agents |
Non-Patent Citations (1)
| Title |
|---|
| SEIFEN, OLE, FETTE, WACHSE Bd. 102, Nr. 19, 1976, AUGSBURG DE Seite 557 G.SCHMIDT 'Die in der Kosmetik gebra}chlichen bakteriziden Wirkstoffe' in der Anmeldung erwähnt * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07500097A (en) | 1995-01-05 |
| DE4132772A1 (en) | 1993-04-08 |
| EP0606290A1 (en) | 1994-07-20 |
| AU2640692A (en) | 1993-05-03 |
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