DE3143048C2 - - Google Patents

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Publication number
DE3143048C2
DE3143048C2 DE19813143048 DE3143048A DE3143048C2 DE 3143048 C2 DE3143048 C2 DE 3143048C2 DE 19813143048 DE19813143048 DE 19813143048 DE 3143048 A DE3143048 A DE 3143048A DE 3143048 C2 DE3143048 C2 DE 3143048C2
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DE
Germany
Prior art keywords
dihydro
dimethoxy
antimicrobial
water
antimicrobial agents
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE19813143048
Other languages
German (de)
Other versions
DE3143048A1 (en
Inventor
Werner Dipl.-Chem. Dr. 4010 Hilden De Gerhardt
Rudolf Dipl.-Biol. Dr. 4040 Neuss De Lehmann
Karlheinz Dipl.-Chem. Dr. 5657 Haan De Disch
Friedrich-Wilhelm Dr. 2082 Moorrege De Kohlmann
Dieter Dr.-Chem. 6701 Dannstadt-Schauernheim De Degner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19813143048 priority Critical patent/DE3143048A1/en
Publication of DE3143048A1 publication Critical patent/DE3143048A1/en
Application granted granted Critical
Publication of DE3143048C2 publication Critical patent/DE3143048C2/de
Granted legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Dentistry (AREA)
  • Dermatology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Detergent Compositions (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)

Description

Die vorliegende Erfindung betrifft die Verwendung von 2,5-Dihydro-2,5-dialkoxy-2,5-dialkylfuran-Derivaten als antimikrobielle Mittel.The present invention relates to the use of 2,5-dihydro-2,5-dialkoxy-2,5-dialkylfuran derivatives as antimicrobial agents.

Die Desinfektion mit chemischen Verfahren gewinnt ge­ genüber physikalischen Verfahren besonders aufgrund wirtschaftlicher Überlegungen an Bedeutung.The disinfection with chemical methods wins ge especially due to physical processes economic considerations of importance.

Es besteht ein Bedürfnis nach antimikrobiell wirksamen Substanzen, welche ein breites mikrobizides Wirkungsspektrum und hohe Wirksamkeit bei gleichzeitig geringer Toxizität haben.It exists a need for antimicrobial substances, which has a broad microbicidal spectrum of activity and high effectiveness with low toxicity to have.

In der DE-AS 24 33 836 sind 2,5-Dialkoxy-2,5-di- oder tetrahydrofuranverbindungen mit sporizider Wirkung beschrieben. Ihre mikrobistatische und bakteri­ zide Wirkung, insbesondere gegen Staph. aureus ist nicht befriedigend.In DE-AS 24 33 836 2,5-dialkoxy-2,5-di- or tetrahydrofuran compounds with sporicider Effect described. Your microbial and bacteri Zide effect, especially against staph. aureus is not satisfying.

Es wurde nun gefunden, daß 2,5-Dihydro-2,5-dialkoxy- 2,5-dialkylfurane der allgemeinen Formel (I)It has now been found that 2,5-dihydro-2,5-dialkoxy 2,5-dialkylfurans of the general formula (I)

wobei R¹ und R² für einen Alkylrest mit 1-4 Kohlen­ stoffatomen stehen, eine bessere bakterizide und fun­ gizide Wirksamkeit haben. Die erfindungsgemäß verwend­ baren Stoffe stellen somit eine Bereicherung der Tech­ nik dar.wherein R¹ and R² represent an alkyl group of 1-4 carbons atoms, a better bactericidal and fun have gicidal activity. The invention uses ble substances thus enrich the tech nik dar.

Die 2,5-Dihydro-2,5-dialkoxy-2,5-dialkylfuran-Derivate sind aus den entsprechenden 2,5-Dihydro-2,5-dialkyl- furanen durch anodische Alkoxylierung herstellbar. Die­ ses Herstellungsverfahren ist in der DE-AS 27 10 420 beschrieben.The 2,5-dihydro-2,5-dialkoxy-2,5-dialkylfuran derivatives are from the corresponding 2,5-dihydro-2,5-dialkyl furans produced by anodic alkoxylation. the This production process is described in DE-AS 27 10 420 described.

Zur Verwendung in antimikrobiellen Mitteln können die Verbindungen gemäß Formel I mit üblichen Träger- und Hilfsstoffen, sowie gegebenenfalls in Kombination mit weiteren bekannten antimikrobiellen Stoffen zu Lösungen, Emulsionen, Salben, Pasten, Gelen, Puder oder Sprays verarbeitet werden. Neben der Wasserlöslichkeit stellt besonders die gute Öllöslichkeit einen anwendungstech­ nischen Vorteil dar, da diese Verbindungen sehr leicht in praktisch alle ölhaltigen Produkte einarbeitbar sind. Es ist zweckmäßig, die antimikrobiellen Wirkstoffe in einer Konzentration von 0,005 bis 5 Gewichtspro­ zent, bezogen auf die zur Anwendung kommende Zuberei­ tung, einzusetzen.For use in antimicrobial agents, the Compounds according to formula I with conventional carrier and Excipients, and optionally in combination with other known antimicrobial substances to solutions, Emulsions, ointments, pastes, gels, powders or sprays are processed. In addition to the water solubility poses especially the good oil solubility an appstech niche advantage because these compounds are very light can be incorporated into practically all oil-containing products are. It is convenient to use the antimicrobial agents in a concentration of 0.005 to 5 weight per cents, based on the application to be used to use.

Die erfindungsgemäßen Mittel können auf den verschiedensten Gebieten zum Einsatz gelangen, beispielsweise als Reinigungs-, Desinfektions- und Kon­ servierungsmittel für Kosmetik, Textilien, Fußböden, Krankenhauseinrichtungen, medizinische Instrumente, Schulen, Badeanstalten, öffentliche Verkehrsmittel, gewerbliche Betriebe sowie in Molkereien, Brauereien oder Wäschereien. The agents according to the invention can used in a variety of fields, For example, as a cleaning, disinfecting and Kon preservatives for cosmetics, textiles, floors, Hospital facilities, medical instruments, Schools, public baths, public transport, commercial enterprises as well as in dairies, breweries or laundries.  

Für flüssige Zubereitungen kommen als Lösungsmittel Wasser und übliche organische Lösungsmittel, insbe­ sondere Alkohole, gegebenenfalls im Gemisch mit Was­ ser in Betracht. Solche Lösungen lassen sich gut ver­ sprühen, wobei man entweder Druckluft anwendet oder ein in der Aerosoltechnik für die Herstellung von Sprays übliches Treibmittel einsetzt. Desweiteren kann man an sich bekannte Lösungsmittler einarbei­ ten, wozu außer den wasserlöslichen, niedermolekula­ ren, aliphatischen Alkoholen mit 1 bis 4 Kohlenstoff­ atomen auch die sogenannten hydrotropen Stoffe vom Typ der niederen Alkylarylsulfonate, beispielsweise Toluol-, Xylol- oder Cumolsulfonat gehören. Diese können auch in Form ihrer Natrium- oder Kalium- oder Alkylammoniumsalze vorliegen. Auch wasserlösliche Ether oder wasserlösliche bzw. mit Wasser emulgierba­ re Ketone kommen in Betracht.For liquid preparations come as a solvent Water and common organic solvents, esp particular alcohols, optionally in admixture with what into consideration. Such solutions can be ver well spray using either compressed air or a in the aerosol technology for the production of Sprays uses conventional propellant. Furthermore you can einarbei known solubilizers besides the water-soluble, low molecular weight ren, aliphatic alcohols having 1 to 4 carbon also the so-called hydrotropic substances of Type of lower alkylarylsulfonates, for example Toluene, xylene or cumene sulfonate. These can also be in the form of their sodium or potassium or Alkyl ammonium salts are present. Also water soluble Ether or water-soluble or emulsified with water re ketones come into consideration.

Wenn neben der antimikrobiellen Wirkung eine zusätz­ liche Reinigungswirkung erwünscht wird, können die Mittel praktisch alle üblichen Tenside enthalten. In den antimikrobiellen Mitteln können auch Gerüststubstan­ zen vorhanden sein; als solche eignen sich sauer bis schwach sauer reagierende anorganische oder organische Salze, insbesondere organische oder anorganische Kom­ plexbildner.If in addition to the antimicrobial effect an additional Liche cleaning effect is desired, the Means contain virtually all conventional surfactants. In The antimicrobial agents may also be scaffold stucco be present zen; as such are suitable sour to weakly acidic inorganic or organic Salts, in particular organic or inorganic com formers.

Die folgenden Beispiele sollen die Erfindung näher erläutern. The following examples are intended to illustrate the invention in more detail explain.  

Beispiel 1Example 1

In der flüssigen Hemmreihe und im Suspensionstest in Anlehnung an die Richtlinien für die Prüfung von che­ mischen Desinfektionsmittel der Deutschen Gesellschaft für Hygiene und Mikrobiologie (3. Auflage, 1972), wur­ de die Verbindung 2,5-Dimethoxy-2,5-dimethyl-dihydro­ furan auf ihre mikrobiologische Wirkung getestet.In the liquid inhibition series and in the suspension test in Following the guidelines for the examination of che mix disinfectant of the German society for Hygiene and Microbiology (3rd edition, 1972), wur de the compound 2,5-dimethoxy-2,5-dimethyl-dihydro furan tested for its microbiological activity.

1. Flüssige Hemmreihe1. Liquid inhibition series

geprüfte Konzentrationen: 1000; 500; 250; 100; 50; 10 ppm
Durchführung in Standard I-Bouillon (pH 7,5) bzw. Würze-Bouillon (pH 5,5).tested concentrations: 1000; 500; 250; 100; 50; 10 ppm
Procedure in standard I broth (pH 7.5) or wort broth (pH 5.5).

Die minimalen Hemmkonzentrationen in ppm sind in folgender Tabelle zusammengefaßt.The minimum inhibitory concentrations in ppm are in summarized in the following table.

Prüfkeimetest organisms MHK (ppm)MIC (ppm) Staph. aureusStaph. aureus 250250 E. coliE. coli 100100 Ps. aeruginosaPs. Aeruginosa 10001000 Cand. albicansCand. albicans 10001000 Trichoph. ment.Trichoph. ment. 5050

2. Suspensionstest2. Suspension Test

Wirkstoffansatz in demin. Wasser
geprüfte Einwirkzeiten: 15; 60; 120 Minuten
Einwirktemperatur: Raumtemperatur
Impfsuspension 1 : 100 in Wirkstoffansatz verdünnt
Enthemmung in der Subkultur: Tween-LecithinDrug preparation in demin. water
tested exposure times: 15; 60; 120 minutes
Reaction temperature: room temperature
Vaccine suspension diluted 1: 100 in drug mixture
Disinhibition in subculture: Tween lecithin

Die Abtötungszeiten in Minuten sind in folgender Tabelle zusammengefaßt.The kill times in minutes are as follows Table summarized.

Beispiel 2example 2

Es wurde die Verbindung 2,5-Dimethyl-2,5-dimethoxy-2,5- dihydrofuran (A) und die Verbindung 2,5-Dimethoxy-2,5- dihydrofuran (B) in der flüssigen Hemmreihe, im Suspensionstest und Flächentest auf ihre mikrobi­ statischen und mikrobiziden Wirkungen untersucht. Die Ergebnisse sind in folgenden Tabellen zusammen­ gefaßt: It was the compound 2,5-dimethyl-2,5-dimethoxy-2,5- dihydrofuran (A) and the compound 2,5-dimethoxy-2,5- dihydrofuran (B) in the liquid inhibitor series, in the Suspension test and area test on their mikrobi static and microbicidal effects. The results are summarized in the following tables focus:  

1. Flüssige Hemmreihe 1. Liquid inhibition series

2. Suspensionstest 2nd suspension test

3. Flächendesinfektionstest 3. Surface disinfection test

Keimfreiheit nach × Stunden Sterility after × hours

Verwendung als antimikrobielle SubstanzenUse as antimicrobial substances

Nachstehend werden einige Zubereitungen angegeben, in die die erfindungsgemäß zu verwendenden Furan- Derivate eingearbeitet wurden. (GT = Gewichtsteile)Below some preparations are given, into which the furan to be used according to the invention Derivatives were incorporated. (GT = parts by weight)

1. Desinfizierendes Reinigungsmittel für harte Oberflächen1. Disinfecting detergent for hard surfaces

13 GT C₁₀-C₁₂-Fettalkohol + 10 EO (Ethylenoxid)
10 GT 2,5-Dihydro-2,5-dimethoxy-2,5-dimethylfuran
5 GT Nitrilotriessigsäure, Na-Salz
10 GT Dipropylenglykolmonomethylether
62 GT Wasser13 GT C₁₀-C₁₂ fatty alcohol + 10 EO (ethylene oxide)
10 parts by weight of 2,5-dihydro-2,5-dimethoxy-2,5-dimethylfuran
5 GT nitrilotriacetic acid, Na salt
10 parts by weight of dipropylene glycol monomethyl ether
62 GT water

2. Flächendesinfektionsmittel2. Surface disinfectant

15 GT Nonylphenyol + 10 EO (Ethylenoxid)
12 GT 2,5-Dihydro-2,5-dimethoxy-2,5-dimethyl-furan
7 GT Dodecyl-benzyl-dimethylammoniumchlorid
10 GT Isopropanol
56 GT Wasser15 GT nonylphenol + 10 EO (ethylene oxide)
12 GT 2,5-dihydro-2,5-dimethoxy-2,5-dimethyl-furan
7 pbw of dodecyl-benzyl-dimethylammonium chloride
10 GT isopropanol
56 GT water

3. Desinfizierende Handwaschpaste3. Disinfecting hand washing paste

25 GT Kokosfettsäureamidopropyl-dimethyl-amino- essigsäure-betain
3 GT Kokosfettsäureethanolamid
43 GT Bimsstein, fein gemahlen
0,5 GT 2,5-Dihydro-2,5-dimethoxy-2,5-dimethyl-furan
28,5 GT Wasser 25 GT Kokosfettsäureamidopropyl-dimethyl-amino-acetic acid betaine
3 GT coconut fatty acid ethanolamide
43 GT pumice, finely ground
0.5 part of 2,5-dihydro-2,5-dimethoxy-2,5-dimethyl-furan
28.5 GT of water

4. Pflege-Spray4. Care Spray

60 GT Öl
5 GT 2,5-Dihydro-2,5-dimethoxy-2,5-dimethyl- furan
30 GT Treibgas60 GT oil
5 GT 2,5-dihydro-2,5-dimethoxy-2,5-dimethyl-furan
30 GT propellant

Claims (4)

1. Antimikrobielles Mittel, gekennzeichnet durch einen Gehalt an mindestens einem 2,5-Dihydro-2,5-dialkoxy- 2,5-dialkylfuranderivat der allgemeinen Formel (I) wobei R¹ und R² für einen Alkylrest mit 1-4 Koh­ lenstoffatomen stehen.1. Antimicrobial agent, characterized by a content of at least one 2,5-dihydro-2,5-dialkoxy-2,5-dialkylfuranderivat of the general formula (I) wherein R¹ and R² represent an alkyl radical having 1-4 carbon atoms. 2. Antimikrobielles Mittel, gekennzeichnet durch einen Gehalt an 2,5-Dihydro-2,5-dimethoxy-2,5-dimethyl- furan.2. Antimicrobial agent, characterized by a Content of 2,5-dihydro-2,5-dimethoxy-2,5-dimethyl furan. 3. Verwendung von antimikrobiellen Mitteln gemäß An­ spruch 1 bis 2 für die Konservierung von Kosmetika.3. Use of antimicrobial agents according to An Claims 1 to 2 for the preservation of cosmetics. 4. Verwendung von antimikrobiellen Mitteln gemäß An­ spruch 1 bis 2 für die Reinigung und Desinfektion von medizinischen Instrumenten, Krankenhauseinrich­ tungen, Fußböden oder Textilien.4. Use of antimicrobial agents according to An Terms 1 to 2 for cleaning and disinfection of medical instruments, hospital equipment doors, floors or textiles.
DE19813143048 1981-10-30 1981-10-30 Antimicrobial agents comprising 2,5-dihydro-2,5-dialkoxy- 2,5-dialkylfuran derivatives Granted DE3143048A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19813143048 DE3143048A1 (en) 1981-10-30 1981-10-30 Antimicrobial agents comprising 2,5-dihydro-2,5-dialkoxy- 2,5-dialkylfuran derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19813143048 DE3143048A1 (en) 1981-10-30 1981-10-30 Antimicrobial agents comprising 2,5-dihydro-2,5-dialkoxy- 2,5-dialkylfuran derivatives

Publications (2)

Publication Number Publication Date
DE3143048A1 DE3143048A1 (en) 1983-05-05
DE3143048C2 true DE3143048C2 (en) 1989-10-19

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DE19813143048 Granted DE3143048A1 (en) 1981-10-30 1981-10-30 Antimicrobial agents comprising 2,5-dihydro-2,5-dialkoxy- 2,5-dialkylfuran derivatives

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2561448C1 (en) * 2014-04-16 2015-08-27 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический универистет" (ФГБОУ ВПО "КубГТУ") Method of increasing sowing qualities of spring wheat seeds and sustainability of seedlings to water stress

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2433836C3 (en) * 1974-07-15 1979-03-22 Schuelke & Mayr Gmbh, 2000 Norderstedt Disinfectant with sporadic effects

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