NO135852B - - Google Patents

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NO135852B
NO135852B NO3055/73A NO305573A NO135852B NO 135852 B NO135852 B NO 135852B NO 3055/73 A NO3055/73 A NO 3055/73A NO 305573 A NO305573 A NO 305573A NO 135852 B NO135852 B NO 135852B
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gluconate
lactate
weight
solution
chlorhexidine
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NO3055/73A
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Norwegian (no)
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NO135852C (en
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Wilhelm Hurka
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Wilhelm Hurka
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Publication of NO135852C publication Critical patent/NO135852C/no

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/40Biocides, 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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42Biocides, 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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44Guanidine; Derivatives thereof

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Foreliggende oppfinnelse angår et desinfeksjonsmiddel som i vandig oppløsning som virksomt stoff inneholder salter av klorheksidin (dvs. 1,1<1->heksametylen-bis-[5-(p-klor-fenylbiguanid)]) og salter av en kvaternær ammoniumbase, og midlet karakteriseres ved at begge de virksomme stoffer foreligger som glukonat eller laktat. The present invention relates to a disinfectant which in aqueous solution as active ingredient contains salts of chlorhexidine (i.e. 1,1<1->hexamethylene-bis-[5-(p-chloro-phenylbiguanide)]) and salts of a quaternary ammonium base, and the remedy is characterized by the fact that both active substances are present as gluconate or lactate.

Konsentrasjonen av klorheksidinlaktatet eller -glukonatet utgjør hensiktsmessig 0,1-15 vekt-%, fortrinnsvis 4 vekt-%, og den til laktatet eller glukonatet av den kvaternære ammoniumbase 1-20 vekt-%, fortrinnsvis 5 vekt-%. The concentration of the chlorhexidine lactate or gluconate is suitably 0.1-15% by weight, preferably 4% by weight, and that of the lactate or gluconate of the quaternary ammonium base 1-20% by weight, preferably 5% by weight.

Som kvaternære ammoniumbaser skal f.eks. nevnes følgende forbindelser: dodecyldimetyldiklorbenzylammoniumlaktat dodecyldimetylbenzylammoniumlaktat tetradecyldimetylbenzylammohiumlaktat dodecyldimetyletylbenzylammoniumlaktat heksadecyltrimetylammoniumlaktat As quaternary ammonium bases, e.g. the following compounds are mentioned: dodecyldimethyldichlorobenzylammonium lactate dodecyldimethylbenzylammonium lactate tetradecyldimethylbenzylammonium lactate dodecyldimethylethylbenzylammonium lactate hexadecyltrimethylammonium lactate

dodecyldimetyldiklorbenzylammoniumglukonat dodecyldimetylbenzylammoniumglukonat dodecyldimethyldichlorobenzylammonium gluconate dodecyldimethylbenzylammonium gluconate

tetradecyldimetylbenzylammoniumglukonat dodecyldimetyletylbenzylammoniumglukonat heksadecyltrimetylammoniumglukonat. tetradecyldimethylbenzylammonium gluconate dodecyldimethylethylbenzylammonium gluconate hexadecyltrimethylammonium gluconate.

Klorheksidinglukonat har god virksomhet mot gramnegative kimer, og de kvaternære ammoniumsalter har god virksomhet mot grampositive kimer, spesielt mot Staphylokokkér. Disse virkninger utfyller seg ved kombinasjonen av de to stoffer på fordelaktig måte. Chlorhexidine gluconate has good activity against Gram-negative germs, and the quaternary ammonium salts have good activity against Gram-positive germs, especially against Staphylococcus. These effects are complemented by the combination of the two substances in an advantageous way.

Den minst like gode virksomhet mot gramnegative kimer tilkommer klorheksidinlaktatet. Dette utmerker seg i til- Chlorhexidine lactate has the least equally good activity against Gram-negative germs. This excels in to-

legg ved en spesielt god hudfordragelighet. add a particularly good skin tolerance.

Det, nye klorheksidinlaktat oppnås idet man omsetter melkesyre eller et salt av ,denne syre med klorheksidin eller et salt av denne forbindelse. The new chlorhexidine lactate is obtained by reacting lactic acid or a salt of this acid with chlorhexidine or a salt of this compound.

Det er kjent desinfeksjonsmidler som i oppløst til-stand inneholder de to virksomme stoffer klorheksidinglukonat og et kvaternært ammoniumhalogénid. Disinfectants are known which in a dissolved state contain the two active substances chlorhexidine gluconate and a quaternary ammonium halide.

Disse preparater har dog den store mangel at klor-heksidinet forener seg med halogenidet, spesielt kloridet, i ammoniumbasen, og dette'gir et uoppløselig bunnfall. Derfor er fremstillingen av slike oppløsninger kun mulig med en tilleggs-tilsetning av oppløsningsfremmende stoffer (polyoksyetylenglykoler), og til og med i dette tilfelle kan det kun bringes en liten konsentrasjon (0,15 vekt-%) åv klorheksidinglukonat i oppløsning, hvis oppløsningen skal forbli klar. However, these preparations have the major disadvantage that the chlorhexidine combines with the halide, especially the chloride, in the ammonium base, and this gives an insoluble precipitate. Therefore, the preparation of such solutions is only possible with an additional addition of dissolution-promoting substances (polyoxyethylene glycols), and even in this case only a small concentration (0.15% by weight) of chlorhexidine gluconate can be brought into solution, if the solution is to stay ready.

En ytterligere mangel ligger i at tilsetning av oppløsningsfremmende stoffer (polyoksyetylenglykoler) nedsetter den bioside virksomhet av preparatet. A further shortcoming is that the addition of dissolution-promoting substances (polyoxyethylene glycols) reduces the biocidal activity of the preparation.

Ifølge oppfinnelsen anvendes for første gang i stedet for halogenidet av det kvaternære ammoniumsalt det tilsvarende glukonat henholdsvis laktat. På denne måte kan klorheksidin ikke mer falle ut som halogenid, og oppløsningen forblir klar, uten at det tilsettes dppløsningsfremmende stoffer. According to the invention, the corresponding gluconate or lactate is used for the first time instead of the halide of the quaternary ammonium salt. In this way, chlorhexidine can no longer precipitate as a halide, and the solution remains clear, without the addition of dissolution-promoting substances.

Konsentrasjonen av klorheksidinlaktat henholdsvis The concentration of chlorhexidine lactate respectively

-glukonat slik som nevnt ovenfor utgjør opptil 15 vekt-%. Virksomheten blir ikke nedsatt ved tilsetning av et oppløsnings- fremmende stoff. På grunn av de kvaternære ammoniumsalter gir det seg en hurtig inntreden av virkningen og virksomheten mot grampositive kimer; på grunn av;klorheksidinlaktatet henholdsvis -glukonatet en vedvarende virksomhet og virkning mot gramnegative kimer. Substansen er filmdannende, overflåteaktiv og tåles godt av huden. -gluconate as mentioned above constitutes up to 15% by weight. The business is not reduced by the addition of a dissolution promoting substance. Because of the quaternary ammonium salts, there is a rapid onset of action and activity against gram-positive germs; due to the chlorhexidine lactate and -gluconate a persistent activity and effect against Gram-negative germs. The substance is film-forming, surface-active and well tolerated by the skin.

Fremstillingseksempler: Production examples:

Fremstilling av 1,1<1->heksametylen-bis-[5-(p-klorfenylbiguanid)]-dilaktat. Preparation of 1,1<1->hexamethylene bis-[5-(p-chlorophenylbiguanide)]-dilactate.

En blanding av 5,05 g 1,1r<->heksametylen-bis-[5-(p-klorfenylbiguanid)] og 2,0 g melkesyre (90%-ig) oppløses i 50 ml vann og oppvarmes lett (30°C). A mixture of 5.05 g of 1,1r<->hexamethylene-bis-[5-(p-chlorophenylbiguanide)] and 2.0 g of lactic acid (90%) is dissolved in 50 ml of water and heated slightly (30°C ).

Det filtreres og avkjøles, og man oppnår en klar, bestandig oppløsning av 1,1'-heksametylen-bis-[5-(p-klorfenyl-biguanid) ]dilaktat. It is filtered and cooled, and a clear, stable solution of 1,1'-hexamethylene bis-[5-(p-chlorophenyl-biguanide)]dilactate is obtained.

Fremstilling av dodecyldimetyldiklorbenzylammoniumglukonat. 2 1 av en 20%-ig vandig "Benzalkon B"-oppløsning (dodecyldimetyldiklorbenzylammoniumklorid) lar man flyte over 50 g av den sterkt basiske ionebytter "Merck III". Til den oppnådde oppløsning settes 70 g glukono-6-lakton og pH-verdien innstilles på denne måte til 7,0. Innholdet justeres ved hjelp av vann til 20%. Oppløsningen inneholder under 0,1% klorid. Preparation of dodecyldimethyldichlorobenzylammonium gluconate. 2 1 of a 20% aqueous "Benzalkon B" solution (dodecyldimethyldichlorobenzylammonium chloride) is allowed to flow over 50 g of the strongly basic ion exchanger "Merck III". 70 g of glucono-6-lactone are added to the solution obtained and the pH value is adjusted in this way to 7.0. The content is adjusted using water to 20%. The solution contains less than 0.1% chloride.

Kun på denne måte oppnår man en oppløsning" med tilstrekkelig liten kloridkonsentrasjon. This is the only way to achieve a solution with a sufficiently low chloride concentration.

Det skal fremheves at en behandling med alkali og derpå følgende nøytralisering av "Benzalkon B"-basen med glukon-syre-6-lakton ikke gir det tilstrekkelig lave kloridinnhold. "Benzalkon B"-glukonat som fremstilles ved behandling med alkali osv., ga med klorheksidinglukonat uklare oppløsninger.- It should be emphasized that a treatment with alkali and subsequent neutralization of the "Benzalkon B" base with gluconic acid-6-lactone does not give it a sufficiently low chloride content. "Benzalkon B" gluconate, which is prepared by treatment with alkali, etc., gave with chlorhexidine gluconate cloudy solutions.-

På samme måte kan også de følgende glukonater av kavternære ammoniumbaser fremstilles fra tilsvarende halogenider: dodecyldimetylbenzylammoniumglukonat tetradecyldimetylbenzylammoniumglukonat dodecyldimetyletylbenzylammoniumglukonat og heksadecyltrimetylammoniumglukonat. In the same way, the following gluconates of quaternary ammonium bases can also be prepared from corresponding halides: dodecyldimethylbenzylammonium gluconate tetradecyldimethylbenzylammonium gluconate dodecyldimethylethylbenzylammonium gluconate and hexadecyltrimethylammonium gluconate.

Fremstilling av dodecyldimetyldiklorbenzylammoniumlaktat.. 30 ml av en 20%-ig vandig "Benzalkon B'l<->oppløsning (dodecyldimetyldiklorbenzylammoniumklorid) lar man flyte over 500 g av den sterkt basiske ionebytter "Merck III". Preparation of dodecyldimethyldichlorobenzylammonium lactate.. 30 ml of a 20% aqueous "Benzalkon B'l<-> solution (dodecyldimethyldichlorobenzylammonium chloride) is allowed to flow over 500 g of the strongly basic ion exchanger "Merck III".

Til denne oppnådde oppløsning settes 36 g 90%-ig melkesyre, og pH-verdien innstilles på denne måte til 7,0.. Opp-løsningen inneholder under 0,1% klorid. 36 g of 90% lactic acid is added to this obtained solution, and the pH value is adjusted in this way to 7.0. The solution contains less than 0.1% chloride.

Eksempel 1 Example 1

20% av en 20%-ig klorheksidinglukonatoppløsning og 25 g av en 20%-ig dodecyldimetyldiklorbenzylammoniumglukonat-oppløsning helles sammen. Dertil settes 55 g vann, og det røres godt. 20% of a 20% chlorhexidine gluconate solution and 25 g of a 20% dodecyldimethyldichlorobenzylammonium gluconate solution are poured together. Add 55 g of water to this and stir well.

Man oppnår 100 g av en oppløsning som oppviser et innhold på 4 vekt-% klorheksidinglukonat og 5 vekt-% dodecyldi- 100 g of a solution with a content of 4% by weight of chlorhexidine gluconate and 5% by weight of dodecyl di-

raetyldiklorbenzylammoniumglukonat. raethyldichlorobenzylammonium gluconate.

Analogt fremspilles blandinger av klorheksidinglukonat og følgende kvaternære ammoniumsalter: dodecy.ldimetylbenzy lammoniumglukonat tetradecyldimetylbenzylammoniumglukonat d<p>decyldlmetyletylbenzylammoniumglukonat, og heksadecyltrimetylammoniumglukonat. Analogously, mixtures of chlorhexidine gluconate and the following quaternary ammonium salts are produced: dodecyldimethylbenzylammonium gluconate tetradecyldimethylbenzylammonium gluconate d<p>decyldlmethylethylbenzylammonium gluconate, and hexadecyltrimethylammonium gluconate.

Eksempel 2 Example 2

20 g av en 20%-ig klorheksidinlaktatoppløsning og 25 g av en 20%-ig dodecyldimetyldiklorbenzylammoniumlaktat-oppløsning forenes. 20 g of a 20% chlorhexidine lactate solution and 25 g of a 20% dodecyldimethyldichlorobenzylammonium lactate solution are combined.

Dertil settes 55 g vann pg det omrøres. Man oppnår en oppløsning som.oppviser et innhold på 4 vekt-% klorheksidinlaktat og 5 vekt-% dodecyldimetyldiklorbenzylammoniumlaktat. Add 55 g of water to it and stir. A solution is obtained which has a content of 4% by weight of chlorhexidine lactate and 5% by weight of dodecyldimethyldichlorobenzylammonium lactate.

Analogt fremstilles blandinger av klorheksidinlaktat og følgende kvaternære ammoniumsalter: dodecyldimetylbenzylammoniumlaktat tetradecyldimetylbenzylammoniumlaktat dodecyldimetyletylbenzylammoniumlaktat, <p>g heksadecyltrimetylammoniumlaktat. Analogously, mixtures of chlorhexidine lactate and the following quaternary ammonium salts are prepared: dodecyldimethylbenzylammonium lactate tetradecyldimethylbenzylammonium lactate dodecyldimethylethylbenzylammonium lactate, <p>g hexadecyltrimethylammonium lactate.

Eksempel 3 Example 3

20 g av,en 20%-ig klorheksidindiglukonatoppløsning og 25 g av 20%-ig dodecyldimetyldiklorbenzylammoniumlaktat-oppløsning forénes. Dertil settes 55 g og det omrøres. 20 g of a 20% chlorhexidine digluconate solution and 25 g of a 20% dodecyldimethyldichlorobenzylammonium lactate solution are combined. Add 55 g to it and stir.

Man oppnår 100 g av en oppløsning som oppviser et innhold på 4 vekt-% klorheksidindiglukonat og 5 vekt-% dode-cyldimetyldikiorbenzylammoiirumlaktat. 100 g of a solution is obtained which has a content of 4% by weight of chlorhexidine digluconate and 5% by weight of dodecyldimethyldichlorobenzylammonium lactate.

Eksempel 4 Example 4

20 g av én 20%-ig klorheksidindilaktatoppløsning og 25 g av en 20%-ig dodecyldimetyldiklorbenzylammoniumglukonat-oppløsning forénes. 20 g of a 20% chlorhexidine dilactate solution and 25 g of a 20% dodecyldimethyldichlorobenzylammonium gluconate solution are combined.

Dertil settes 55 g vann og man omrører. Man oppnår 100 g av en oppløsning som oppviser et innhold på 4 vekt-% klorheksidindilaktat og 5 vekt-% dodecyldimetyldiklorbenzylammoniumglukonat. Add 55 g of water and stir. 100 g of a solution is obtained which has a content of 4% by weight chlorhexidine dilactate and 5% by weight dodecyldimethyldichlorobenzylammonium gluconate.

Claims (2)

1. Desinfeksjonsmiddel som i vandig oppløsning som virksomt stoff inneholder salter av 1,1<1->heksametylen-bis-[5-(p-klorfenylbiguanid)] og en kvaternær ammoniumbase fra gruppen dodecyldimetyldiklorbenzylammonium-, dodecyldimetylbenzylammon-ium-, tetradecyldimetylbenzylammonium-, dodecyldimetyletylbenzyl-ammonium- og heksadecyltrimetylammoniumhydroksyd, karakterisert ved at begge de virksomme stoffer foreligger som glukonat eller laktat.1. Disinfectant which in aqueous solution as active ingredient contains salts of 1,1<1->hexamethylene-bis-[5-(p-chlorophenylbiguanide)] and a quaternary ammonium base from the group dodecyldimethyldichlorobenzylammonium-, dodecyldimethylbenzylammonium-, tetradecyldimethylbenzylammonium-, dodecyldimethylethylbenzylammonium and hexadecyltrimethylammonium hydroxide, characterized in that both active substances are present as gluconate or lactate. 2. Desinfeksjonsmiddel ifølge krav 1, karakterisert ved at 1,1'-heksametylen-bis-[5-(p-klorfenyl-biguanid) ] laktatet henholdsvis -glukonatet foreligger i en konsentrasjon fra 0,1-15 vekt-%, fortrinnsvis 4. vekt-%, og laktatet henholdsvis glukonatet av den kvaternære ammoniumbase foreligger i en konsentrasjon fra 1-20 vekt-%, fortrinnsvis 5 vekt-%.2. Disinfectant according to claim 1, characterized in that the 1,1'-hexamethylene-bis-[5-(p-chlorophenyl-biguanide)] lactate or -gluconate is present in a concentration of from 0.1-15% by weight, preferably 4 % by weight, and the lactate or gluconate of the quaternary ammonium base is present in a concentration of 1-20% by weight, preferably 5% by weight.
NO3055/73A 1972-07-31 1973-07-30 NO135852C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AT659572A AT318152B (en) 1972-07-31 1972-07-31 Disinfectants

Publications (2)

Publication Number Publication Date
NO135852B true NO135852B (en) 1977-03-07
NO135852C NO135852C (en) 1977-06-15

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AT (1) AT318152B (en)
AU (1) AU468341B2 (en)
BE (1) BE802957A (en)
CA (1) CA1026232A (en)
DD (1) DD106780A5 (en)
FI (1) FI58424C (en)
FR (1) FR2194448B1 (en)
GB (1) GB1355636A (en)
IL (1) IL42716A (en)
NL (1) NL7306479A (en)
NO (1) NO135852C (en)
SE (1) SE397268B (en)
ZA (1) ZA735201B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE425043B (en) * 1977-05-10 1982-08-30 Kenogard Ab FUNGICID COMPOSITION, PREFERRED FOR USE AS A THREE PROTECTIVE, CONTAINING AT LEAST ONE QUARTER OF AMMONIUM SUBSTANCE IN MIXING WITH AN AMINE COMPONENT
AT381001B (en) * 1983-11-28 1986-08-11 Arcana Chem Pharm METHOD FOR PRODUCING CLEAR AQUEOUS DISINFECTANT SOLUTIONS
FR2691325B1 (en) * 1992-05-21 1997-06-06 Hutchinson ANTISEPTIC COMPOSITIONS AND THEIR APPLICATIONS.
IL100881A (en) * 1992-02-06 1996-06-18 Porat Michael Prophylactic lubricating composition and devices and method for using same
US6303557B1 (en) 1999-11-16 2001-10-16 S. C. Johnson Commercial Markets, Inc. Fast acting disinfectant and cleaner containing a polymeric biguanide
WO2010010345A2 (en) * 2008-07-22 2010-01-28 Polybiotech Limited Sanitising compositions and methods
GB2474017B (en) * 2009-09-29 2015-07-15 Europ First Aid Ltd Biocidal solution

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Publication number Publication date
NO135852C (en) 1977-06-15
AU468341B2 (en) 1976-01-08
DD106780A5 (en) 1974-07-05
CA1026232A (en) 1978-02-14
SE397268B (en) 1977-10-31
NL7306479A (en) 1974-02-04
FI58424B (en) 1980-10-31
AT318152B (en) 1974-09-25
IL42716A0 (en) 1973-10-25
ZA735201B (en) 1974-09-25
DE2310989B2 (en) 1975-06-26
DE2310989A1 (en) 1974-02-14
FI58424C (en) 1981-02-10
BE802957A (en) 1973-11-16
FR2194448B1 (en) 1976-09-17
FR2194448A1 (en) 1974-03-01
GB1355636A (en) 1974-06-05
AU5869973A (en) 1975-01-30
IL42716A (en) 1976-03-31

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