DE1643848B1 - N-2-AEthylhexyl-N'-arylharnstoffe und ihre Verwendung als Bakterizide - Google Patents

N-2-AEthylhexyl-N'-arylharnstoffe und ihre Verwendung als Bakterizide

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Publication number
DE1643848B1
DE1643848B1 DE19681643848D DE1643848DA DE1643848B1 DE 1643848 B1 DE1643848 B1 DE 1643848B1 DE 19681643848 D DE19681643848 D DE 19681643848D DE 1643848D A DE1643848D A DE 1643848DA DE 1643848 B1 DE1643848 B1 DE 1643848B1
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Germany
Prior art keywords
general formula
atom
bactericides
ethylhexyl
aethylhexyl
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.)
Pending
Application number
DE19681643848D
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English (en)
Inventor
Max Dr Duennenberger
Dieter Dr Duerr
Hans-Rudolf Dr Hitz
Max Dr Schellenbaum
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Priority claimed from CH41767A external-priority patent/CH467019A/de
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of DE1643848B1 publication Critical patent/DE1643848B1/de
Pending legal-status Critical Current

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    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
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    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C07C273/1818—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from -N=C=O and XNR'R"
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    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
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    • C07C275/38—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by doubly-bound oxygen atoms
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    • C07C335/04—Derivatives of thiourea
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    • C07D263/18—Oxygen atoms
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    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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  • General Health & Medical Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Dermatology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

0x3.2
in der X1 und X3 je ein Wasserstoffatom, ein Chloratom, ein Bromatom, ein Chloratom, ein Bromatom oder eine Trifluormethylgruppe, X2 ein Wasserstoffatom, ein Chloratom oder ein Bromatom, jedoch mindestens eines und höchstens zwei der Symbole X1, X2 und X3 Wasserstoffatome bedeutet.
Die Verbindungen der allgemeinen Formel (I) werden durch Umsetzung eines Isocyanates der allgemeinen Formel
X1 -
45
in der X1, X2 und X3 die angegebene Bedeutung haben, mit 2-Äthylhexyl-l-amin erhalten.
Mittel zur Bekämpfung schädlicher Bakterien, welche einen N-2-Äthylhexyl-N'-aryl-harnstoff der allgemeinen Formel (I) enthalten, können in üblicher Weise hergestellt und angewandt werden. Besonders wertvoll an solchen Mitteln ist das breite, sich sowohl auf grampositive wie auch auf gramnegative Bakterien erstreckende Wirkungsspektrum. Hierbei ist in anwendungstechnischer Hinsicht die Geruchlosigkeit und Farblosigkeit der Verbindungen der allgemeinen Formel (I) von besonderem Wert. Die vorliegende Erfindung umfaßt somit ebenfalls deren Einsatz in der Bekämpfung von Bakterien ganz allgemein. Die Verwendung ist auf sehr breiter Basis möglich, insbesondere zum Schutz von organischen Substraten gegen den Befall durch zerstörende und pathogene Bakterien. Die Verbindungen der allgemeinen Formel (I) eignen sich demnach als Konservierungsmittel und auch als Desinfektionsmittel für Textilien und technische Produkte aller Art, in der Veterinärmedizin und in der Kosmetik.
Unter den technischen Produkten, welche mit Verbindungen der allgemeinen Formel (I) geschützt bzw. versetzt werden können, seien die folgenden als Beispiele herausgegriffen: Natürliche und künstliche Textilfasern, Textilhilfsmittel bzw. Veredlungsmittel, Leime, Bindemittel, Anstrichmittel, Färb- bzw. Druckpasten, Waschmittel und andere Zubereitungen. Der Wirkstoffgehalt kann je nach Anwendungszweck zwischen 1 und 30 g/l betragen. Die Wirkstoffe lassen sich auch zur Verhütung der bakteriellen Schleimbildung in Rohrsystemen, vor allem in Vorrichtungen der Papierindustrie verwenden.
Die in den nachfolgenden Beispielen angegebenen Teile sind Gewichtsteile, die Prozente Gewichtsprozente, sofern nichts anderes angegeben.
Beispiel
37,6 Teile 3,4-Dichlorphenylisocyanat werden zu einer Lösung von 25,9 Teilen 2-Äthylhexyl-(l)-amin in 200 Volumteilen Benzol gegeben. Durch Zugabe von 200 Volumteilen Petroläther wird der entstandene N-3,4-Dichlorphenyl-N'-2-äthyl-hexyl-(l)-harnstoff (= Verbindung A) gefällt. Die Ausbeute beträgt ungefähr 57 Teile.
Q5H22ON2Cl2:
Berechnet ... N 8,83, Cl 22,35%;
gefunden .... N 8,70, Cl 22,64%.
In analoger Weise können die Verbindungen B bis H der Tabelle I hergestellt werden, der die allgemeine Formel II zugrunde hegt:
R-NH-CO-NH-CH2-CH-(CH2)3-CH3 (II)
C2H5
Tabelle I
Vergleichsversuch
Verbindung
F3C
F3C
F3C
Schmelzpunkt 0C
65 bis 66
75 bis 76
Siedepunkt 100bisl05/0,15mmHg
72 bis 73
Antibakterielle Wirkung im Verdünnungstest
Eine l%ige und eine 0,3%ige Lösung der Wirkstoffe in Dimethylsulfoxid werden je in ein Röhrchen mit steriler Fleischbouillon gegeben. Mit diesen Lösungen werden fortlaufende 1:10-Verdünnungen angesetzt, und durch Kombination der beiden entstehenden Reihen erhält man folgende kontinuierliche Verdünnungsreihe: 1000, 300, 100, 30,10, 3 ppm usw.
Die Lösungen werden mit dem Bakterium Staphylococcus aureus beimpft. Anschließend wird während 48 Stunden bei 37° C bebrütet (Bakteriostase).
Nach 24 Stunden Kulturdauer wird aus den Röhrchen eine öse auf Glucose-Agarplatten ausgestrichen und während 24 Stunden bei 37° C bebrütet (Bakterizidie).
Im Vergleich mit Dimethyllaurylbenzylammoniumchlorid (DLBA), das unter dem Namen »Benzalkon A« als Bakterizid im Handel vertrieben wird, werden für die erfindungsgemäßen Verbindungen nach den genannten Zeiten die in der Tabelle II aufgeführten Grenzkonzentrationswerte ermittelt.
64 bis 65 30 Verbindung 35 A. Tabelle II ration in ppm
Bakterizide
60 bis 61 B Grenzkonzent
Bakteriostase		 1
51 bis 52 C 1 . 3,5
1
D 1
1		 1
3
40 E 0,6
2		 5
12
F 4
10
34 bis 36 DLBA (bekannt) ..

Claims (1)

  1. Patentansprüche: 1. N-2-Äthylhexyl-N-aryl-harnstoffe der allgemeinen Formel
    NH-C-HN-CH2-CH-CH2-CH2-Ch2-CH3
    in der X1 und X3 je ein Wasserstoffatom, ein Chloratom, ein Bromatom oder eine Trifluormethylgruppe, X2 ein Wasserstoffatom, ein Chloratom oder ein Bromatom, jedoch mindestens einer und höchstens zwei der Substituenten X Wasserstoffatome bedeutet.
    2. Verwendung der N-2-Äthyl-N -aryl-harnstoffe gemäß Anspruch 1 als Bakterizide.
    Gegenstand der Erfindung sind bakterizide N-2-Äthylhexyl-N-aryl-harnstoffe der allgemeinen Formel (I)
    NH-C-HN-CH2-Ch-CH2-CH2-CH2-CH3
DE19681643848D 1967-01-12 1968-01-03 N-2-AEthylhexyl-N'-arylharnstoffe und ihre Verwendung als Bakterizide Pending DE1643848B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH41767A CH467019A (de) 1967-01-12 1967-01-12 Gebrauchsfertiges Mittel zur Bekämpfung von schädlichen Bakterien auf textilen Materialien
CH1446267 1967-10-17

Publications (1)

Publication Number Publication Date
DE1643848B1 true DE1643848B1 (de) 1972-01-13

Family

ID=25684520

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19681643848D Pending DE1643848B1 (de) 1967-01-12 1968-01-03 N-2-AEthylhexyl-N'-arylharnstoffe und ihre Verwendung als Bakterizide

Country Status (10)

Country Link
US (1) US3592932A (de)
AT (1) AT279058B (de)
BE (1) BE709240A (de)
CA (1) CA961052A (de)
DE (1) DE1643848B1 (de)
FR (1) FR1575560A (de)
GB (1) GB1173872A (de)
IT (1) IT972013B (de)
NL (1) NL6800445A (de)
SE (1) SE332422B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0297610A1 (de) * 1987-07-02 1989-01-04 Warner-Lambert Company N-[(2,6-disubstituierte)-Phenyl]-Harnstoff und -Carbamat-Inhibitoren der Acyl-Coenzym A:Cholesterol-Acyltransferase

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988294A (en) * 1974-03-11 1976-10-26 R. T. Vanderbilt Company, Inc. Surface coating compositions containing antimicrobic ureas
EP1019367A1 (de) * 1997-08-05 2000-07-19 Novo Nordisk A/S Derivate von 2,5- und 3,5-disubstituierten anilinen, ihre herstellung und verwendung
US8293751B2 (en) 2003-01-14 2012-10-23 Arena Pharmaceuticals, Inc. 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
PL378295A1 (pl) * 2003-02-24 2006-03-20 Arena Pharmaceuticals, Inc. Podstawione pochodne arylowe i heteroarylowe jako modulatory metabolizmu glukozy oraz profilaktyka i leczenie zaburzeń tego metabolizmu
AR045047A1 (es) * 2003-07-11 2005-10-12 Arena Pharm Inc Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
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CN110520124A (zh) 2017-02-16 2019-11-29 艾尼纳制药公司 用于治疗原发性胆汁性胆管炎的化合物和方法

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EP0297610A1 (de) * 1987-07-02 1989-01-04 Warner-Lambert Company N-[(2,6-disubstituierte)-Phenyl]-Harnstoff und -Carbamat-Inhibitoren der Acyl-Coenzym A:Cholesterol-Acyltransferase

Also Published As

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BE709240A (de) 1968-07-11
IT972013B (it) 1974-05-20
US3592932A (en) 1971-07-13
FR1575560A (de) 1969-07-25
NL6800445A (de) 1968-07-15
SE332422B (de) 1971-02-08
AT279058B (de) 1970-02-25
CA961052A (en) 1975-01-14
GB1173872A (en) 1969-12-10

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