DE10016371A1 - Use of 3-iodo-2-propynyl carbamates as an antimicrobial agent - Google Patents

Abstract

The invention relates to the use of 3-iodine-2-propinyl-carbamates as antimicrobial, especially antimycotic, active agents in washing agents, cleaning agents, hand washing agents, hand washing-up liquids, washing-up liquids for dishwashers and agents for finishing textiles, furs or leather.

Description

The present invention relates to the use of 3-iodo-2-propynyl carbamates as antimicrobial, especially antimycotic agents in Detergents; Detergents; Hand washing agents; Hand dishwashing detergents; Dishwasher detergents and agents for finishing textiles, furs, Skins or leather.

Hygiene in the washing and cleaning process does not only mean elimination visible contamination, but also to make Kei harmless men who use the goods to be cleaned, e.g. laundry, have contaminated. Such germs are viruses and bacteria, but especially Mushrooms. Hygiene is particularly important, especially laundry hygiene ne, therefore in the commercial sector, where from hospitals, hotels, restaurants textiles that are not within a certain circulate among the user group, but from different uses who are needed. But hygiene also wins in the household sector aspect is becoming increasingly important, especially because more and more textiles that worn directly on the body, such as underwear, lingerie or stockings fe consist of fabrics with washing temperatures of 40 ° C or above, Do not tolerate proteases and bleach-active substances, so that mild detergents ver must be used, the germicidal effect of which is only slight.

For ecological reasons - not least because of the voluntary commitment of the Industry to reduce energy consumption - have been the washing process in their hygienic parameters (temperature, washing times and liquors ratio) always minimized.

As a result, all of these factors together can lead to germs, who have contaminated the laundry while wearing it, no longer in the washing process  be made sufficiently harmless and later reused lead to hygienic problems. In addition, washing and rinsing machines, especially those that are not used for a long time, by star No germ growth in hoses, the pump or the induction chamber if it leads to hygienic problems and olfactory nuisance. If laundry remains damp in the washing machine for a longer period of time, can fungal - it leads to the well-known foxing.

From EP-B-0 093 962 2- (3-iodo-2-propynyloxy) ethyl carbamates and de use for the preservation of technical products (e.g. paints, Glues, dispersions, cooling lubricants), for the antimicrobial finishing of Joint sealants, to combat mold on walls, ceilings or wooden floors, for the antimicrobial finishing of plastics such. B. PVC films and known as preservatives for cosmetics.

From Appendix 6 of the Cosmetics Ordinance is 3-iodo-2-propynyl butyl carbamate (IPBC) known as a preservative.

The at the time of filing the present invention unpublished Published DE-A-199 19 770.9 of the applicant mentions the use of IPBC in nanoscale form as an antimicrobial agent in the mouth and / or Dental care.

The at the time of filing the present invention unpublished Published DE-A-199 19 769.5 of the applicant mentions the use of IPBC in nanoscale form as an antimicrobial agent in body deodorants.

The present invention has for its object to provide means which have an antimicrobial and in particular antimycotic effect and to overcome the above disadvantages of the prior art are suitable.  

Surprisingly, it was found that 3-iodo-2-propynyl-carbamate, in particular special IPBC, also as a component of detergents and cleaning agents anti have microbial and in particular antimycotic activity. This The finding was particularly surprising because it was from the state of the art Technically known uses of 2- (3-iodo-2-propynyloxy) ethyl carbamaten and from IPBC the need for the permanent retention of the Active ingredient in the pro to be preserved or antimicrobially equipped duct suggest.

The present invention therefore relates to the use of 3-iodine-2- propynyl carbamates of the formula (I), as an antimicrobial and in particular anti mycotic active ingredient in detergents; Detergents; Hand washing agents; Hand dishwashing detergents and machine dishwashing detergents as well as textile, fur and leather finishing agents.

The 3-iodo-2-propynylcarbamates which can be used according to the invention correspond to the general formula (I)

in which R ¹ and R ^{2 are the} same or different and are hydrogen, linear or branched alkyl radicals having 1 to 6 carbon atoms;
R ³ , R ⁴ , R ⁵ and R ⁶ , which may be the same or different, denote hydrogen or alkyl radicals having 1 to 4 carbon atoms;
R is hydrogen, linear or branched alkyl radicals having 1 to 12 carbon atoms or a cyclohexyl radical, a phenyl radical, a substituted phenyl radical, a benzyl radical or a p-toluenesulfonyl radical and n is 0 or 1.

A carbamate which can preferably be used according to the invention is IPBC, which corresponds to the formula I, where R ¹ and R ^{2 are} hydrogen, n is 0 and R is butyl - (- C ₄ H ₉ ), in particular n-butyl.

The compounds which can be used according to the invention are inherently known processes known in the art, in particular as in EP-B-0 093 962, to which reference is hereby made in full is taken.

The 3-iodo-2-propynylcarbamates are prepared, for example, by equimolar amounts of the alcohols of the general formula (II)

with suitable isocyanates of the general formula (III),

OCN-R (III)

where in the formulas (II) and (III) the symbols R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R as well as n have the meanings given for the formula (I).

Examples of linear or branched alkyl radicals having 1 to 6 carbon atoms, for which R ¹ and R ² are, are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl and their branched isomers.

Compounds of the formula (I) in which both substituents R ¹ and R ^{2 are} simultaneously hydrogen or methyl at the same time are preferably used, such as those in which one of R ¹ and R ^{2 is} hydrogen while the other is methyl.

Examples of alkyl radicals having 1 to 4 carbon atoms, which R ³ , R ⁴ , R ⁵ and R ⁶ represent, are methyl. Ethyl, propyl, isopropyl, n-butyl, isobutyl. sec-butyl and tert-butyl, with methyl being preferred.

Compounds which can be used with preference are those of the general formula (I) in which at least 4 of the radicals R ¹ to R ⁶ are hydrogen. Examples of linear and branched alkyl radicals with 1 to 12 carbon atoms. R stands for methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert.-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the branched isomers of Alkyls with 5 to 12 carbon atoms.

Examples of substituted phenyl radicals which R represents are chlorophenyl, Bromophenyl, fluorophenyl, dichlorophenyl and trichlorophenyl.

Compounds in which R is a lower alkyl radical are preferably usable 1 to 4 carbon atoms or a phenyl radical or one with chlorine or bromine substituted phenyl radical.

Examples of particularly preferred compounds are those in where R is propyl, butyl or phenyl.

The N-substituted 3-iodo-2-propynyl-carbamates of the general formula (I) who the methods known per se (Houben-Weyl, methods of the Org. Chemie, Vol. 8, pp. 141-144 (1952)) by reacting equimolar amounts of Alcohols of the general formula (II) with suitable, for. B. commercially available Chen isocyanates of the general formula (III) synthesized.

The reaction is carried out at temperatures from about 10 ° C to about 70 ° C. before preferably carried out from about 20 ° C to about 30 ° C.

The reactions are generally carried out in an inert solvent guided. Examples include ethylene chloride, dimethylformamide, toluene, chlorine called benzene, methylene chloride and tetrahydrofuran.

The reactions can be accelerated with the help of catalysts. As Catalysts such as dibutyltin dilaurate have proven suitable. Further  usable catalysts are: dibutyltin diacetate and tert. Bases like Triethylamine.

The alcohols of the general formula (II) can be prepared according to Ver drive through iodination of propargyl alcohol or substituted propargyl alcohol get (n = 0) or in two reaction stages by reacting propargyl alcohol hol or substituted propargyl alcohols with ethylene oxide or substituted Epoxides and subsequent iodination of the propynyloxy alcohols obtained (n = 1) can be produced.

Examples of alcohols of the general formula (II) are:
3-iodo-2-propinol,
2- (3-iodo-2-propynyloxy) ethanol,
2- (4-iodo-3-butyn-2-yloxy) ethanol,
1- (3-iodo-2-propynyloxy) -2-propanol and
1- (2-hydroxyethoxy) -1-iodoethynyl cyclohexane.

Examples of isocyanates are methyl isocyanate, ethyl isocyanate, propyl isocyanate, Butyl isocyanate, phenyl isocyanate, 4-chlorophenyl isocyanate, cyclohexyl isocyanate, 4-fluorophenyl isocyanate, 3,4-dichlorophenyl isocyanate, 2,4,5-trichlorophenyl isocy anate and p-toluenesulfonyl isocyanate.

The 3-iodo-2-propynylcarbamates which can be used according to the invention are in the Those skilled in the art are familiar with the liquid agents in which they have their effect should unfold, added. For use in solid funds, the inventions 3-iodo-2-propynylcarbamates which can be used according to the invention are either the liquid or pasty raw materials can be added, from which you get the solid agent manufactures, or applied to the solid means, for example by Spraying.

The 3-iodo-2-propynyl which can be used according to the invention are preferably carbamate the detergent; Detergents; Hand washing agents; Handge dishwashing detergents; Dishwashing detergents and equipment for washing  Textiles, furs, furs or leather in an organic solvent, esp especially in alcoholic solution, particularly preferably in ethanolic solution added.

Likewise preferred are the 3-iodo-2- propinyl-carbamate added to the above agents in nanoscale form. Nanoscale substances are substances whose particle diameter water in the direction of the greatest expansion of the particles less than 1000 nm (Nanometers). In particular, the particle diameter is the invented 3-iodo-2-propynylcarbamates which can be used according to the invention are about 5 to 500 nm, be preferably 10 to 150 nm. In the present document it becomes synonymous with the term "nanoscale" also the term "nanoparticulate" used.

The nanoscale active ingredients which can be used according to the invention consist of egg ner discrete phase of the active ingredient, on the surface of which preferably min at least a surface-modifying substance is adsorbed.

Emulsifiers are particularly suitable as surface-modifying substances and / or protective colloids. The coating of the particles with emulsifiers and / or protective colloids leads to the fact that subsequent agglomeration of the Particle does not take place.

Examples of suitable emulsifiers are nonionic surfactants from at least one of the following groups:

• 1. Addition products of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles Propylene oxide on linear fatty alcohols with 8 to 22 carbon atoms, on fatty acid ren with 12 to 22 carbon atoms and alkylphenols with 8 to 15 carbon atoms in the alkyl group;
• 2. C _12/18 fatty acid _monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol;
• 3. Glycerol mono- and diesters and sorbitan mono- and diesters of saturated ten and unsaturated fatty acids with 6 to 22 carbon atoms and de ren ethylene oxide addition products;  
• 4. Alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl rest and their ethoxylated analogues;
• 5. Addition products of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil;
• 6. Polyol and especially polyglycerol esters, such as. B. Polyglycerol polyri cinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several are also suitable this substance classes;
• 7. Adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil;
• 8. _{partial esters} based on linear, branched, unsaturated or saturated C _6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerin, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g. sorbitol), sucrose, alkyl glucosides ( e.g. methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (e.g. cellulose);
• 9. Mono-, di- and trialkyl phosphates as well as mono-, di- and / or tri-PEG- alkyl phosphates and their salts;
• 10. wool wax alcohols;
• 11. Polysiloxane-polyalkyl-polyether copolymers or corresponding deriva te;
• 12. Mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE-PS 11 65 574 and / or mixed esters of fatty acids with 6 to 22 Carbon atoms, methyl glucose and polyols, preferably glycerin or polyglycerin as well
• 13. Polyalkylene glycols.

The adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. gemi cal, the average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out. C _12/18 fatty acid _monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 20 24 051 as refatting agents for cosmetic preparations.

C _8/18 alkyl mono- and oligoglycosides, their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms. Regarding the glycoside residue, both monoglycosides, in which a cyclic sugar residue is glycosidically bound to the fatty alcohol, and oligomeric glycosides with a degree of oligomerization of up to approximately 8 are suitable. The degree of oligomerization is a statistical mean value, which is based on a usual homolog distribution for such technical products.

Typical examples of anionic emulsifiers are soaps, alkylbenzenesulfona te, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, α-methyl ester sulfonates, sulfo fatty acids, alkyl sulfates, fatty alcohol ether sulfates, Glycerol ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, Fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dial kylsulfo-succinamate, sulfotriglycerides, amide soaps, ether carboxylic acids and de ren salts, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, N- Acylamino acids such as acyl lactylates, acyl tartrates, acyl glutamates and acyl aspartates, alkyl oligoglucoside sulfates, protein fatty acid condensates (ins special vegetable products based on wheat) and alkyl (ether) phosphates. If the anionic surfactants contain polyglycol ether chains, they can a conventional, but preferably a narrow, homolog distribution have lung.

Zwitterionic surfactants can also be used as emulsifiers. Such surface-active compounds are called zwitterionic surfactants referred to, which in the molecule at least one quaternary ammonium group and carry at least one carboxylate and one sulfonate group. Particularly suitable  zwitterionic surfactants are so-called betaines such as N-alkyl N, N-dimethylammoniumglycinate, for example trimethylammoniumgly cinat, cocoalkyldimethylammonium glycinate, N-acylamino-propyl-N, N- dimethylammonium glycinate, for example cocoacylaminopropyldi methylammonium glycinate, and 2-alkyl-3-carboxylmethyl-3-hydroxyethylimida zolines each having 8 to 18 carbon atoms in the alkyl or acyl group and that Coconut acylaminoethyl hydroxyethyl carboxymethyl glycinate. Particularly preferred is the fat known under the CTFA name Cocamidopropyl Betaine acid amide derivative.

Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a C _8/18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO ₃ H group in the molecule and are capable of forming internal salts . Examples of suitable ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylamino butter acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycines, N-alkyltaurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids, each with about 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are the N-coconut alkyl aminopropionate, the coconut acylaminoethyl aminopropionate and the C _12/18 acyl sarcosine. In addition to the ampholytic emulsifiers, quaternary emulsifiers are also suitable, those of the ester quat type, preferably methyl quaternized difatty acid triethanolamine ester salts, being particularly preferred. Typical examples of anionic emulsifiers are alkyl sulfates, alkyl ether sulfates and monoglyceride (ether) sulfates.

As a rule, the active ingredients and the emulsifiers are in a weight ratio 1: 100 to 100: 1, preferably 1:25 to 25: 1 and in particular 1:10 to 10: 1 used. Particularly preferred are those emulsifiers which are used for Training of microemulsions are capable.

Suitable protective colloids are e.g. B. gelatin, casein, gum arabic, lysal bic acid, starch, carboxymethyl cellulose or modified carboxymethyl cellulose  as well as polymers such as polyvinyl alcohols, polyvinyl pyrrolidones, polyal kylene glycols and polyacrylates.

The 3-iodo-2-propynylcarbamates which can be used according to the invention can also are used as nanoparticles by one or more emulsifiers and / or protective colloids are encased.

Corresponding nanoparticles can be produced, for example, by

• a) 3-iodo-2-propynyl carbamate in a liquid phase in which it is not soluble are contributing
• b) the resulting mixture above the melting point of 3-iodo-2-propynyl carbamate warmed,
• c) the resulting oil phase an effective amount of at least one emul gators closes and finally
• d) the emulsion below the melting point of the 3-iodo-2-propynyl-carbamates cools.

Another process for the production of nanoparticles by rapid ent tension of supercritical solutions (Rapid Expansion of Supercritical Solu RESS) is, for example, from the article by S. Chihlar, M. Türk and K. Schaber in Proceedings World Congress on Particle Technology 3, Brighton, Known in 1998. To prevent the nanoparticles from reassembling it is advisable to use the starting materials in the presence of a suitable protective column solids or emulsifiers to dissolve and / or the critical solutions in aqueous and / or alcoholic solutions of the protective colloids or emulsifiers or a To relax in cosmetic oils, which in turn dissolved Emul gators and / or protective colloids can contain.

Another suitable method for producing the nanoscale particles offers evaporation technology. Here, the starting materials are first in a suitable organic solvent (e.g. alkanes, vegetable oils, Ethers, esters, ketones, acetals and the like) dissolved. Then the  Such solutions in water or another non-solvent in which Usually in the presence of a surface-active compound dissolved in it ben that it can not be mixed with each other by the homogenization of the two ren solvent to a precipitation of the nanoparticles, the or ganic solvent preferably evaporated. Instead of an aqueous solution O / W emulsions or O / W microemulsions can also be used become. As surface-active compounds, they can already be mentioned at the beginning explained emulsifiers and protective colloids can be used. Another There is the possibility of producing nanoparticles in the so-called GAS (Gas Anti Solvent Recrystallization) process. The process uses one highly compressed gas or supercritical fluid (e.g. carbon dioxide) as non- Solvent for the crystallization of solutes. The compressed gas phase it is introduced into the primary solution of the starting materials and absorbed there, whereby the liquid volume increases, the solubility decreases and finely divided particles are excreted.

The PCA method (Precipitation with a Compressed Fluid Anti-solvent). Here the primary solution of the starting materials is supercritical introduced fluid, whereby finely divided droplets are formed in which Dif fusion processes take place so that the finest particles are precipitated. At the PGSS (Particles from Gas Saturated Solutions) are the end materials by pressing on gas (e.g. carbon dioxide or propane) melted. Pressure and temperature reach near or supercritical conditions conditions. The gas phase dissolves in the solid and causes a lowering of the Melting temperature, viscosity and surface tension. At the ex expansion through a nozzle, fine cooling occurs due to cooling effects ter particle.

The production processes listed for the nanoparticles according to the invention are to be understood only as examples and do not constitute a restriction.

The concentration of the 3-iodo-2-propynyl which can be used according to the invention carbamate in the compositions can be used by the person skilled in the art in a wide range  can be varied depending on the conditions in which the agents are used. The stake amount of the dissolved or nanoscale 3-iodo-2-propynyl-carbamate is so ge chooses that the concentration of the 3-iodo-2-propynyl carbamates is usually in on the order of 0.001 to 5, preferably 0.01 to 2 and in particular 0.1 to 1 wt .-% based on the preparations.

Other objects of the present invention are detergents; Reini conditioner; Rinse aid; Hand wash; Hand dishwashing liquid; Maschi Dishwashing detergents and preparations for finishing textiles, furs, furs or leather containing a 3-iodo-2-propynylcarbamate of the formula (I) or more 3- Contain iodine-2-propynyl carbamates, especially those containing IPBC. Preferred objects of the present invention are detergents; Reini conditioner; Rinse aid; Hand wash; Hand dishwashing liquid; Maschi Dishwashing detergents and preparations for finishing textiles, furs, furs or leather, the 3-iodo-2-propynyl-carbamate, in particular IPBC, in nanopar ticular form were added.

Another object of the present invention is the use of 3- Iodine-2-propynyl-carbamates of the formula I, in particular from IPBC, as an antimicro biological and in particular antimycotic active ingredient in antimicrobial agents len finishing of textiles, furs, furs or leather.

Further objects of the present invention are textiles, furs, furs or leather, equipped with an agent according to the invention.

The finishing of the textiles, furs, skins or leather takes place in the specialist known manner, for example by immersing the textiles, furs, furs or leather in a suitably concentrated solution of an inventive Means.

The following examples illustrate the invention without, however, going into it restrict:  

1.1. Test substances

IPBC (30% in dipropylene glycol), obtained from Milker & Grüning GmbH, Horhausen, was because of the poor water solubility as follows prediluted:

An alcoholic stock solution with 1% active ingredient was prepared by weighing 3.34 g of 30% IPBC in 100 ml of 99% ethanol and subsequently diluting it in double dist. H ₂ O further diluted to the required test solutions. These were:
2 ml stock solution ad 200 ml bidist. H ₂ O → 100 ppm IPBC (= 0.99% ethanol)
10 ml stock solution ad 200 ml bidist. H ₂ O → 500 ppm IPBC (= 4.95% ethanol)
15 ml stock solution ad 200 ml bidist. H ₂ O → 750 ppm IPBC (= 7.42% ethanol)

An antibacterial and antimycotic Re formula used, the 70% by weight didecyldimethylammonium chloride, 15% by weight Ethylene glycol, balance water included. The reference product was also diluted with bidistilled water.

1.2. Test mushrooms

Candida albicans, ATCC 10231, (pre-cultivation on CaSo agar, 4d / 25 ° C), Aspergillus niger, ATCC 6275, (pre-cultivation on malt agar, 8d / 25 ° C), Trichophyton menfagrophytes, ATCC 9533, (pre-cultivation on malt agar, 8d / 25 ° C), Cladosporium cladosporioides, DSM 62121, (pre-cultivation on malt agar, 8d / 25 ° C), Epicoccum nigrum, self-isolate, (pre-cultivation on malt agar, 8d / 25 ° C)

The inocula were obtained by washing off the pre-cultivated plates with 0.05% Tween® 80 and had the following germ contents:
Candida albicans; 1.9 × 10 ⁹ CFU / ml,
Aspergillus niger 1.0 × 10 ⁷ CFU / ml,
Trichophyton mentagrophytes: 3.4 × 10 ⁷ CFU / ml,
Cladosporium cladosporioides: 5.0 × 10 ⁷ CFU / ml,
Epicoccum nigrum: 1.9 × 10 ⁵ CFU / ml.
(KBE: colony forming unit)

1.3. Testing the fungistatic effectiveness in the inhibition test

1 × 1 cm, pre-washed and autoclaved test specimens from a standard tree wool fabric according to DIN 53919 (WfK Testgewebe-GmbH, Adlerstr. 42, Krefeld) were placed in the test sample for 15 min., then removed sterile and 14 h dried at room temperature. 0.1 ml vaccine suspensions each of the above Test mushrooms were inoculated in liquid malt agar in a petri dish and after initial of the agar 0.1 ml spatulate on the surface of the agar.

The test specimens impregnated with the test solutions were then placed sterile on the agar surface and the dishes were incubated at 25 ° C. for 7 days. The inhibitory effect was then evaluated according to the following scheme:
0 = clear zone of inhibition, indication of the zone of inhibition in mm,
1 = no growth on the test object, but also no inhibition zone,
2 = isolated growth on the test object,
3 = moderate growth on the test object,
4 = uninhibited growth on the test specimen.

1.4. Examination of the fungicidal effectiveness in the DGHM germ carrier test

The examination was based on the guidelines for the examination and evaluator chemical disinfection processes of the German Society for Hygiene ne and microbiology (DGHM), Gustav Fischer Verlag, 1981:

16 pre-washed and autoclaved specimens each were placed in the above-mentioned. Vaccination of the mushrooms and with repeated turning for 15 min. leave in it. The test specimens contaminated in this way were then placed in empty petri transferred to the shells and poured 10 ml of the test solution onto each. After 60 and  120 min. Exposure time at 20 ° C, 2 of the test specimens were removed and briefly transferred to 10 ml inactivator solution in accordance with DGHM guidelines and out of it inoculated on CaSo (Candida) or malt agar plates (other test mushrooms). The Incubation took place at 25 ° C for 7 days. Then the evaluation was qualitative, d. H. Growth yes (+) or no (-).

2 results

2.1. Fungistatic effectiveness of IPBC

2.1.1. The IPBC's inhibitory activity test yielded the following results

2.2. Fungicidal effectiveness of IPBC

2.2.1. Testing the fungicidal activity of IPBC gave the following results (+ = living culture, - = culture killed)

2.2.3. The comparison test with the reference preparation showed for all test mushrooms up to the highest test concentration of 250 ppm positive growth.  

3. Result

IPBC show a very good fungistati in comparison to the reference preparation effectiveness against both dermatophytes and mold stains producing or material-damaging fungi.

Claims (13)

1. Use of 3-iodo-2-propynylcarbamates of the formula (I),
in which R ¹ and R ^{2 are the} same or different and are hydrogen, linear or branched alkyl radicals having 1 to 6 carbon atoms;
R ³ , R ⁴ , R ⁵ and R ⁶ , which may be the same or different, denote hydrogen or alkyl radicals having 1 to 4 carbon atoms;
R is hydrogen, linear or branched alkyl radicals having 1 to 12 carbon atoms or a cyclohexyl radical, a phenyl radical, a substituted phenyl radical, a benzyl radical or a p-toluenesulfonyl radical and n is 0 or 1,
as antimicrobial agents in detergents; Detergents; Rinse aid; Hand washing agents; Hand dishwashing detergents; Dishwasher detergents and agents for the antimicrobial finishing of textiles, furs, skins or leather. 2. Use according to claim 1, wherein as 3-iodo-2-propynyl carbamate IPBC is used. 3. Use according to claim 1 or 2, wherein the 3-iodo-2-propynyl carbamates are used in nanoparticulate form. 4. Use according to one of claims 1 to 3, wherein antimicrobial ins special antimycotic means.   5. detergent; containing a 3-iodo-2-propynyl carbamate or several 3- Iodine-2-propynyl carbamate, especially IPBC. 6. cleaning agents; containing a 3-iodo-2-propynyl carbamate or more 3-iodo-2-propynyl carbamates, especially IPBC. 7. rinse aid; containing a 3-iodo-2-propynyl carbamate or more 3-iodo-2-propynyl carbamates, especially IPBC. 8. hand wash; containing a 3-iodo-2-propynyl carbamate or more right 3-iodo-2-propynyl carbamate, in particular IPBC. 9. dishwashing liquid; containing a 3-iodo-2-propynyl carbamate or several 3-iodo-2-propynyl-carbamates, especially IPBC. 10. Dishwasher detergent containing a 3-iodo-2-propynyl carbamate or more 3-iodo-2-propynyl carbamates, especially IPBC. 11. Contains agents for finishing textiles, furs, skins or leather tend one 3-iodo-2-propynyl carbamate or several 3-iodo-2-propynyl carbamates, especially IPBC. 12. Composition according to one of claims 5 to 11, characterized in that them 3-iodo-2-propynyl-carbamates, especially IPBC, in nanoparticulate form were added. 13. Textiles, furs, skins or leather finished with an agent according to An saying 11 or 12.