DE964635C - Germicidal preparation - Google Patents
Germicidal preparationInfo
- Publication number
- DE964635C DE964635C DES30871A DES0030871A DE964635C DE 964635 C DE964635 C DE 964635C DE S30871 A DES30871 A DE S30871A DE S0030871 A DES0030871 A DE S0030871A DE 964635 C DE964635 C DE 964635C
- Authority
- DE
- Germany
- Prior art keywords
- chloro
- acetoxy
- quinoline
- germicidal
- germicidal preparation
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Agronomy & Crop Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
AUSGEGEBEN AM 23. MAI 1957ISSUED MAY 23, 1957
PATENTSCHRIFTPATENT LETTERING
KLASSE 3Oi GRUPPE 3 INTERNAT. KLASSE A 611 CLASS 3Oi GROUP 3 INTERNAT. CLASS A 611
S 30871 IVa 1301S 30871 IVa 1301
Dr. Rolf Becher, Basel (Schweiz)Dr. Rolf Becher, Basel (Switzerland)
ist als Erfinder genannt wordenhas been named as the inventor
SOLCO Gesellschaft für chemische Laboratorien A. G., Basel (Schweiz)SOLCO Society for Chemical Laboratories A. G., Basel (Switzerland)
Keimtötendes PräparatGermicidal preparation
Patentiert im Gebiet der Bundesrepublik Deutschland vom 28. Oktober 1952 an Patentanmeldung bekanntgemadit am 6. Dezember 1956Patented in the territory of the Federal Republic of Germany on October 28, 1952 Patent application known since December 6, 1956
Patenterteilung bekanntgemadit am 9. Mai Λ957 Die Priorität der Anmeldung in der Sdrweiz vom 11. Oktober 1952 ist in Anspruch genommenPatent granted on May 9, 1957 The priority of the registration in southern Switzerland of October 11, 1952 has been claimed
Die Erfindung betrifft ein keimtötendes Präparat, das als keimtötende Substanz ein halogeniertes 8-Oxychinolinderivat enthält.The invention relates to a germicidal preparation which uses a halogenated germicidal substance Contains 8-oxyquinoline derivative.
Es ist bekannt, in keimtötenden Präparaten die fungizide Wirkung halogenierter 8-Oxychinoline gegen unterschiedliche pathogene Pilze, z. B. Epidermophyton rubrum, Epidermophyton K. W., Trichophyton gypseum, auszunutzen.It is known that the fungicidal effect of halogenated 8-oxyquinolines in germicidal preparations against different pathogenic fungi, e.g. B. Epidermophyton rubrum, Epidermophyton K.W., Trichophyton gypseum, to take advantage of.
Es wurde gefunden, daß sich die spezifische Wirkung solcher keimtötender Präparate ganz wesentlich steigern läßt, wenn man an Stelle der halogenierten 8-Oxychinoline halogenierte 8-Acetoxychinoline der FormelIt has been found that the specific effect of such germicidal preparations is entirely Can be increased significantly if halogenated 8-acetoxyquinolines are used instead of the halogenated 8-oxyquinolines the formula
HaiShark
COCH3 COCH 3
verwendet, in der R ein Halogen- oder Wasserstoffatom und Hai ein Halogerfatom bezeichnet.used, in which R denotes a halogen or hydrogen atom and Hai denotes a halogen atom.
709 522/88709 522/88
Als besonders wirksam hat sich das 5-Chlor-8-aoetoxychinolin gezeigt.5-chloro-8-aoetoxyquinoline has proven to be particularly effective shown.
Von den in ihrem Aufbau der obengenannten Formel entsprechenden halogenieren 8-Acetoxy-S chinolinen sind bereits das 5, 7-Dichlor-8-acetoxychinolin durch einen Hinweis in B e i1 s t e i η , Hptw., Bd. 21, S. 96, Abs. 2, und das 5-Chlor-7-jod-8-acötoxy-chinolin durch emeVeröffentlidiung in den chemischen Berichten, Bd. 85, S. 106 (1952), bekanntgeworden. Weder diese Zitate noch die entsprechende Originalliteratur enthalten Hinweise darauf, daß die fungizide Wirkung der Halogen-8-oxychinoline durch die Acetylierung ganz wesentlich gesteigert werden kann.Of the 8-acetoxy-S halogenates which correspond in their structure to the above formula Quinolines are already the 5, 7-dichloro-8-acetoxyquinoline by a reference in B e i1 s t e i η, Hptw., Vol. 21, p. 96, para. 2, and 5-chloro-7-iodo-8-acetoxy-quinoline by eme publication in the chemical reports, vol. 85, p. 106 (1952), known. Neither these quotations nor the corresponding original literature contain any references on the fact that the fungicidal effect of the halogen-8-oxyquinolines through the acetylation is essential can be increased.
Bei den von der Anmelderin durchgeführten Vergleichsversuchen ergaben sich die folgenden Testwerte:The comparative tests carried out by the applicant resulted in the following Test values:
Fungizide Grenzkonzentration beiEpidermophytonFungicidal limit concentration in Epidermophyton
Kauf mann-WoHKauf mann-WoH
S-Chlor-S-oxychinolin 1 : 500 000S-chloro-S-oxyquinoline 1: 500,000
S-Chlor-S-acetoxy-chinolin 1:1 000 000S-chloro-S-acetoxy-quinoline 1: 1,000,000
S-Chlor-y-jod-S-oxychinolin 1 : 100 000S-chloro-y-iodo-S-oxyquinoline 1: 100,000
3g s-Chlor^-jod-S-acetoxy-chinolin .. 1 : 200 000 3 g of s-chloro ^ -iodo-S-acetoxy-quinoline .. 1: 200,000
5, 7-Dichlor-8-oxychinoli!n 1 : 200 0005, 7-dichloro-8-oxychinoli! N 1: 200,000
5, y-Dichlor-S-acetoxy-chinolin .... 1 : 500 000.5, y-dichloro-S-acetoxy-quinoline .... 1: 500,000.
Die Werte für Trichophyton gypseum sind analog.The values for Trichophyton gypseum are analogous.
Das in der obigen Zusammenstellung genannte besonders wirksame s-Chlor-S-acetoxy-chinolin ist offenbar ein noch neuer Stoff. Ein solches S-Halogen-S-aoetoxy-chinolin läßt sich nach einem Analogieverfahren in der Weise herstellen, daß man 5-Halogen-8-oxychinolin mit einem Acetylierungsmittel, wie z. B. Essigsäureanhydrid, Acetylchlorid usw., zur Reaktion bringt.The particularly effective s-chloro-S-acetoxy-quinoline mentioned in the above list is apparently a new material. Such an S-halo-S-aoetoxy-quinoline can be according to a Prepare analogy process in such a way that 5-halo-8-oxyquinoline is mixed with an acetylating agent, such as B. acetic anhydride, acetyl chloride, etc., to react.
Die Durchführung einer solchen Reaktion wird wesentlich vereinfacht, wenn man bei dieser Reaktion Schwefelsäure als Katalysator benutzt.Carrying out such a reaction is greatly simplified if one is involved in this reaction Sulfuric acid used as a catalyst.
Das Herstellungsverfahren des 5-Halogen-8-acetoxy-chinolin, für das kein Schutz beansprucht wird, ergibt sich ausführlicher aus den folgenden Beispielen.The manufacturing process of 5-halo-8-acetoxy-quinoline, for which no protection is claimed can be seen in more detail from the following Examples.
Beispiel ι . .Example ι. .
Ein Gemisch von ig 5-Chlor-8-oxychinol.in.und 5 g Essigsäureanhydrid, dem einige Tropfen Schwefelsäure als Katalysator zugesetzt werden, wird unter Rückfluß gekocht. Nach beendeter Reaktion wird das Reaktionsgemisch auf Eis gegossen. Es bildet sich ein Niederschlag, der abfiltriert wird. Durch Einengen der Mutterlauge kann eine weitere Portion der Acetylverbindung gewonnen werden. Das s-Chlor-S-acetoxy-chinolin wird in Form grünlichgelber Kristalle erhalten, die bei etwa 8o° C schmelzen.A mixture of ig 5-chloro-8-oxyquinol.in.und 5 g acetic anhydride, to which a few drops of sulfuric acid are added as a catalyst, is refluxed. After the reaction has ended, the reaction mixture is on ice poured. A precipitate forms which is filtered off. By concentrating the mother liquor another portion of the acetyl compound can be obtained. The s-chloro-S-acetoxy-quinoline is obtained in the form of greenish yellow crystals which melt at around 80 ° C.
2 g s-Chlor-S-oxychinolin werden in 25 cm3 Tetrachlorkohlenstoff mit 2 g Acetylchlorid während Ί Stunde unter Rückfluß gekocht. Das Reaktionsgemisch wird zur Entfernung von unverändertem Ausgangsmaterial filtriert. Das Filtrat wird dann zur Trockne eingedampft. s-Chlor-S-acetoxy-chino-Hn wird in Form von grünlichgelben Kristallen erhalten, die bei etwa 8o° C schmelzen.2 g of s-chloro-S-oxyquinoline are refluxed in 25 cm 3 of carbon tetrachloride with 2 g of acetyl chloride for Ί hour. The reaction mixture is filtered to remove unchanged starting material. The filtrate is then evaporated to dryness. s-chloro-S-acetoxy-quino-Hn is obtained in the form of greenish-yellow crystals which melt at around 80 ° C.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH964635X | 1952-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE964635C true DE964635C (en) | 1957-05-23 |
Family
ID=4550602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES30871A Expired DE964635C (en) | 1952-10-11 | 1952-10-28 | Germicidal preparation |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE964635C (en) |
-
1952
- 1952-10-28 DE DES30871A patent/DE964635C/en not_active Expired
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