DE3143048A1 - Antimicrobial agents comprising 2,5-dihydro-2,5-dialkoxy- 2,5-dialkylfuran derivatives - Google Patents

Antimicrobial agents comprising 2,5-dihydro-2,5-dialkoxy- 2,5-dialkylfuran derivatives

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Publication number
DE3143048A1
DE3143048A1 DE19813143048 DE3143048A DE3143048A1 DE 3143048 A1 DE3143048 A1 DE 3143048A1 DE 19813143048 DE19813143048 DE 19813143048 DE 3143048 A DE3143048 A DE 3143048A DE 3143048 A1 DE3143048 A1 DE 3143048A1
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Germany
Prior art keywords
dihydro
dialkoxy
antimicrobial agents
dialkylfuran
derivatives
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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.)
Granted
Application number
DE19813143048
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German (de)
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DE3143048C2 (en
Inventor
Dieter Dr Chem Degner
Karlheinz Dr Dipl-Chem Disch
Werner Dr Dipl-Chem Gerhardt
Friedrich-Wilhelm Dr Kohlmann
Rudolf Dr Dipl-Biologe Lehmann
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority to DE19813143048 priority Critical patent/DE3143048A1/en
Publication of DE3143048A1 publication Critical patent/DE3143048A1/en
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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

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

Abstract

The invention relates to the use of 2,5-dialkyl-2,5-dialkoxy- dihydrofuran derivatives of the formula (I) <IMAGE> where R<1> and R<2> represent an alkyl radical having 1-4 carbon atoms, as antimicrobial agents.

Description

'l2r5-Dihydro-2#5-dialkoxy-2t5-dialkylfuran-Derivate'I2r5-dihydro-2 # 5-dialkoxy-2t5-dialkylfuran derivatives

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

Die Desinfektion mit chemischen Verfahren gewinnt gegenüber physikalischen Verfahren besonders aufgrund wirtschaftlicher Überlegungen an Bedeutung. Es besteht ein Bedürfni's nach antimikrobiell wirksamen Substanzen, welche ein breites mikrobizides Wirkungsspektrum und hohe Wirksamkeit bei gleichzeitig geringer Toxizität haben. In der DE-AS 24 33 836 sind 2,5-Dialkoxy-2,5-di- oder tetrahydrofuranverbindungen mit sporizider Wirkung beschrieben. Ihre mikrobistatische und bakterizide Wirkung, insgesondere gegen Staph. aureus ist nicht befriedigend.Disinfection with chemical methods wins out over physical ones Process especially important due to economic considerations. It exists there is a need for antimicrobial substances which have a broad microbicidal effect Have a spectrum of activity and high effectiveness with low toxicity at the same time. DE-AS 24 33 836 describes 2,5-dialkoxy-2,5-di- or tetrahydrofuran compounds described as having a sporicidal effect. Their microbistatic and bactericidal effect, especially against staph. aureus is not satisfactory.

Es wurde nun gefunden, daß 2,5-Dihydro-2,5-dialkoxy-2,5-dialkylfurane der allgemeinen Formel (I) wobei R1 und 2 für einen Alkylrest mit 1 - 4 Nohlenstoffatonen stehen, eine bessere bakterizide und fungizide Wirksamkeit haben. Dxe~erfindungsgema.J verwendbaren Stoffe stellen somit eine Dereicherung der Technik dar.It has now been found that 2,5-dihydro-2,5-dialkoxy-2,5-dialkylfurans of the general formula (I) where R1 and 2 stand for an alkyl radical with 1 - 4 carbon atoms, have a better bactericidal and fungicidal activity. The substances that can be used according to the invention thus represent an enrichment of the technology.

Die 2,5-Dihydro-2,5-dialkoxy-2,5-dialkylfúran-Derivate sind aus den entsprechenden 2,5-Dihydro-2,5-dialkylfuranen durch anodische Alkoxylierung herstellbar. Dieses Herstellungsverfahren ist in der DE-AS 2 710 420 beschrieben.The 2,5-dihydro-2,5-dialkoxy-2,5-dialkylfúran derivatives are from the corresponding 2,5-dihydro-2,5-dialkylfurans can be prepared by anodic alkoxylation. This manufacturing process is described in DE-AS 2,710,420.

Zur Verwendung in antimikrobiellen Mitteln können die Verbindungen gemäß Formel I mit üblichen Träger- und Hilsstoffen, sowie gegebenenfalls in Kombination mit weiteren bekannten antimikrobiellen Stoffen zu Lösungen, Emulsionen, Salben, Pasten, Gelen, Puder oder Sprays verarbeitet werden. eben der Wasserlöslichkeit stellt besonders die gute öllöslichkeit einen-anwendungstechnischen Vorteil dar, da diese Verbindungen sehr leicht in praktisch alle ölhaltigen Produkte einarbeitbar sind. Es ist zweckmäßig, die antimikrobiellen lVirkstoffe in einer Konzentration von 0,005 bis 5 Gewichtsprozent, bezogen auf die zur Anwendung kommende Zubereitung, einzusetzen. Die erfindungsgemäßen Mittel können auf den verschiedensten Gebieten zum Einsatz gelangen, beispielsweise als Reinigungs-, Desinfektions- und Konservierungsmittel für Kosmetik, Textilien, Fußböden, Krankenhauseinrichtungen, medizinische Instrumente, Schulen, Badeanstalten, öffentliche Verkehrsmittel, gewerbliche Betriebe sowie in Molkereien, Brauereien oder Wäschereien.For use in antimicrobial agents, the compounds can according to formula I with customary carriers and auxiliaries, and optionally in combination with other known antimicrobial substances for solutions, emulsions, ointments, Pastes, gels, powders or sprays can be processed. just the water solubility the good oil solubility in particular represents an application-technical advantage, as these compounds can be easily incorporated into practically all oil-containing products are. It is advisable to use the antimicrobial active ingredients in one concentration from 0.005 to 5 percent by weight, based on the preparation to be used, to use. The agents according to the invention can be used in the most varied of fields are used, for example as cleaning agents, disinfectants and preservatives for cosmetics, textiles, floors, hospital facilities, medical instruments, Schools, bathing establishments, public transport, commercial establishments and in Dairies, breweries or laundries.

Für flüssige Zubereitungen kommen als Lösungsmittel IJassertund übliche organische Lösungsmittel, insbesondere Alkohole, gegebenenfalls im Gemisch mit Wasser in Betracht. Solche Lösungen lassen sich gut versprühen, wobei man entweder Druckluft anwendet oder ein in der Aerosoltechnik für die Herstellung von Sprays übliches Treibmittel einsetzt. Desweiteren kann man an sich bekannte Lösungsvermittler einarbeiten, wozu außer den wasserlöslichen, niedermolekularen, aliphatischen Alkoholen mit 1 bis 4 Kohlenstoffatomen auch die sogenannten hydrotropen Stoffe vom Typ der niederen Alkylarylsulfonate, beispielsweise Toluol-, Xylol- oder Cumolsulfonat gehören. Diese können auch in Form ihrer Natrium- oder Kaliun- oder Alkylammoniumsalze vorliegen. Auch wasserlösliche Ether oder wasserlösliche bzw. mit Wasser emulgierbare Ketone kommen in Betracht.IJassertund usual solvents are used for liquid preparations organic solvents, in particular alcohols, optionally mixed with water into consideration. Such solutions can be sprayed well using either compressed air or one that is common in aerosol technology for the production of sprays Propellant uses. Furthermore, one can incorporate known solubilizers, including the water-soluble, low molecular weight, aliphatic alcohols with 1 up to 4 carbon atoms also the so-called hydrotropes of the lower type Alkyl aryl sulfonates, for example toluene, xylene or cumene sulfonate. These can also be in the form of their sodium, potassium or alkylammonium salts. Also water-soluble ethers or water-soluble or water-emulsifiable ketones is being brought up for consideration.

Wenn neben der antimikrobiellen Wirkung eine zusätzliche Reinigungswirkung erwünscht wird, können die Mittel praktisch alle üblichen Tenside enthalten. In den antimikrobiellen Mitteln können auch Gerüstsubstanzen vorhanden sein; als solche eignen sich sauer bis schwach sauer reagierende anorganische oder organische Salze, insbesondere organische oder anorganische Komplexbildner.If in addition to the antimicrobial effect, an additional cleaning effect if desired, the agents can contain practically all conventional surfactants. In builder substances can also be present in the antimicrobial agents; as such acidic to slightly acidic reacting inorganic or organic salts are suitable, especially organic or inorganic complexing agents.

Die folgenden Beispiele sollen die Erfindung näher erläutern" Beispiel 1 In der flüssigen Hemmreihe und im Suspensionstest in Anlehnung an die Richtlinien für die Prüfung von chemischen Desinfektionsmittel der Deutschen Gesellschaft für Hygiene und Mikrobiologie (3. Auflage, 1972), wurde die Verbindung 2,5-Dimethoxy-2,5-dimethyl-dihydrofuran auf ihre mikrobiologische Wirkung getestet.The following examples are intended to explain the invention in more detail " example 1 In the liquid inhibition series and in the suspension test based on the guidelines for the testing of chemical disinfectants of the German Society for Hygiene und Mikrobiologie (3rd edition, 1972), the compound 2,5-dimethoxy-2,5-dimethyl-dihydrofuran tested for their microbiological effect.

1. Flüssige ilemmreihe: geprüfte Konzentrationen: 1000; 500; 250; 100; 50; 10 ppm Durchführung in Standard I-Bouillon (pH 7,5) bzw.1. Liquid oil series: tested concentrations: 1000; 500; 250; 100; 50; 10 ppm procedure in standard I broth (pH 7.5) or

Würze - Bouillon (pH 5,5). Seasoning - bouillon (pH 5.5).

Die minimalen Hemmkonzentrationen in ppm sind in folgender Tabelle zusammengefaßt. Prüfkeime MHK (ppm) Staph. aureus 250 E. coli 100 Ps. aeruginosa 1000 Cand. albicans 1000 Trichoph. ment. 50 2. Suspensionstest: Wirkstoffansatz in demin. Wasser geprüfte Einwirkzeiten: 15, 60; 120 Minuten Einwirktemperatur: Raumtemperatur Impfsuspension 1 : 100 in Wirkstoffansatz verdünnt Enthemmung in der Subkultur: Tween-Lecithin Die Abtötungszeiten in Minuten sind in folgender Tabelle zusa:iunengefaßt. Prüfkeime Konz. Abtötungszeit (min.) Staph. aureus 2000 ppm 40 Cand. albicans 2000 ppm 80 Beispiel 2 Es wurde die Verbindung 2,5-Dimethyl-2,5-dimethoxy-2.5-dihydrofuran (A) und die Verbindung 2,5-Dimethoxy-2.5-dihydrofuran (13) in der flüssigen lIemmreihe, im Suspensionstest und Flächentest auf ihre mikrobistatischen und mikrobiziden Wirkungen untersucht.The minimum inhibitory concentrations in ppm are summarized in the following table. Test germs MIC (ppm) Staph. aureus 250 E. coli 100 Ps. Aeruginosa 1000 Cand. albicans 1000 Trichoph. ment. 50 2. Suspension test: active ingredient preparation in demin. Water tested exposure times: 15, 60; Exposure temperature for 120 minutes: room temperature. Inoculation suspension diluted 1: 100 in the active substance formulation. Disinhibition in the subculture: Tween lecithin The killing times in minutes are summarized in the following table. Test germ concentration killing time (min.) Staph. aureus 2000 ppm 40 Cand. albicans 2000 ppm 80 EXAMPLE 2 The compound 2,5-dimethyl-2,5-dimethoxy-2,5-dihydrofuran (A) and the compound 2,5-dimethoxy-2,5-dihydrofuran (13) were tested in the liquid clamping series, in the suspension test and area test investigated microbistatic and microbicidal effects.

Die Ergebnisse sind in folgenden Tabellen zusammengefaßt: 1. Flüssige Hemmreihe Art der Keime Staph. E.coli Ps. Cand. Pen. aureus aerug albicans camer. A 250 100 1000 1000 1000 B > 1000 > 1000 > 1000 > 1000 > 1000 (DE-AS 2433836) Zahlen: M H K (ppm) 2. Suspensionstest: Art der Keime Staph. E. Ps. Bac. Cand. pH aureus coli aerug. subt. alb. Keimzahl/ml der 3,8X108 9,8x108 3,4x108 1,7x108 1x108 Impfsuspension Konzentra- tion (ppm) A 3000 # 15 60 # 15 > 120 120 5,2 B 3000 > 120 >120 >120 >120 >120 4,2 Zahlen: Abtötungszeit in (min.) 3. Plächendesinfektionstest Keimfreiheit nach x Stunden Anwendungs- Staph. - aureus Cand. albicans konzentration Holz PVC Holz PVC auf der Fläche A 2000 ppm 1 1 1 1 B 2000 ppm 6 6 4 4 Konfektionierter Wirkstoffansatz: 10 % Wirkstoff 10 % Nonylphenol + 10 Mol Ethylenoxid 80 % Wasser Verwendung als antimikrobielle Substanzen Nachstehend werden einige Zubereitungen angegeben, in die die erfindungsgemäß zu verwendenden Furan-Derivate eingearbeitet wurden. (GT = Gewichtsteile) 1. Desinfizierendes Reinigungsmittel für harte Oberflächen 13 GT C10-C12-Fettalkohol + 10 EO + 10 GT 2.5-Dihydro-2.5-dimethoxy-2.5-dimethylfuran 5 GT Nitrilotriessigsäure, Ua-Salz 10 GT Dipropylenglykolmonomethylether 62 GT Wasser 2. Flachendcsinfektionsmittel 15 GT Nonylphenol + 10 EO 12 GT 2.\5-3ihydro-2.5-dimethoxy-2.5-dimethyl-furan 7 GT odecyl-benzyl-dimethylammoniumchlorid 10 GT Isopropanol 56 GT Wasser 3. Desinfizierende Ilandwaschpaste 25 GT Kokosfettsäreamidopropyl-dimethyl-aminoessigsäure-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 + EO = = Ethylenoyid 4. Pflege-Sprav 60 GT Oel -5 GT 2.5-Dihydro-2.5-dimethoxy-2.5-dimethylfuran 30 GT TreibgasThe results are summarized in the following tables: 1. Liquid inhibition series Type of germs staph. E. coli Ps. Cand. Pen. aureus aerug albicans camer. A 250 100 1000 1000 1000 B>1000>1000>1000>1000> 1000 (DE-AS 2433836) Numbers: MIC (ppm) 2nd suspension test: Type of germs staph. E. Ps. Bac. Cand. pH aureus coli aerug. subt. silly Bacterial count / ml of the 3.8X108 9.8x108 3.4x108 1.7x108 1x108 Vaccine suspension Concentration tion (ppm) A 3000 # 15 60 # 15> 120 120 5.2 B 3000>120>120>120>120> 120 4.2 Numbers: Killing time in (min.) 3rd surface disinfection test sterility after x hours Application staph. - aureus Cand. albicans concentration wood PVC wood PVC on the surface A 2000 ppm 1 1 1 1 B 2000 ppm 6 6 4 4 Formulated active ingredient formulation: 10% active ingredient 10% nonylphenol + 10 mol ethylene oxide 80% water Use as antimicrobial substances Some preparations are given below in which the furan derivatives to be used according to the invention have been incorporated. (Parts by weight = parts by weight) 1. Disinfectant cleaning agent for hard surfaces 13 parts by weight of C10-C12 fatty alcohol + 10 EO + 10 parts by weight 2.5-dihydro-2.5-dimethoxy-2.5-dimethylfuran 5 parts by weight nitrilotriacetic acid, Ua salt 10 parts by weight dipropylene glycol monomethyl ether 62 parts by weight water 2 Flat end disinfectant 15 pbw nonylphenol + 10 EO 12 pbw 2. \ 5-3ihydro-2.5-dimethoxy-2.5-dimethyl-furan 7 pbw odecyl-benzyl-dimethylammonium chloride 10 pbw isopropanol 56 pbw water 3. Disinfecting Iland wash paste 25 pbw coconut fatty acid imidopropyl-dimethylaminoacetic acid -betain 3 parts by weight coconut fatty acid ethanolamide 43 parts by weight pumice stone, finely ground 0.5 part by weight 2.5-dihydro-2.5-dimethoxy-2.5-dimethyl-furan 28.5 parts by weight water + EO = = ethylene oxide 4. Pflege-Sprav 60 parts oil -5 part weight 2.5 Dihydro-2.5-dimethoxy-2.5-dimethylfuran 30 GT propellant

Claims (4)

Patentansprüche 1. Antimikrobielles Mittel, gekennzeichnet durch einen Geiialt an mindestens einem 2X5-Dihydro-2.5-dialkoxy-2.5-dialkylfuranderivat der allgemeinen Formel (I) wobei R1 und R2 für einen Alkylrest mit 1 - 4 Kohlenstoffatomen stehen.Claims 1. Antimicrobial agent, characterized by a compound of at least one 2X5-dihydro-2.5-dialkoxy-2.5-dialkylfuran derivative of the general formula (I) where R1 and R2 stand for an alkyl radical with 1-4 carbon atoms. 2. Antimikrobielles Mittel, gekennzeichnet durch einen Gehalt an 2.5-Dihydro-2.5-dimethyl-2.5-dimethylfuran.2. Antimicrobial agent, characterized by a content of 2.5-dihydro-2.5-dimethyl-2.5-dimethylfuran. 3. Verwendung von antimikrobiellen Mitteln gemäß Anspruch 1 bis 2 für die Konservierung von Kosmetika.3. Use of antimicrobial agents according to claims 1 to 2 for the preservation of cosmetics. 4. Verwendung von antimikrobiellen Mitteln gemäß Ahspruch 1 bis 2 für die Reinigung- und Desinfektion von medizinischen Instrumenten, Krankenhauseinrichtungen, Fußböden oder Textilien.4. Use of antimicrobial agents in accordance with claims 1 to 2 for cleaning and disinfecting medical instruments, hospital facilities, 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)

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DE19813143048 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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DE19813143048 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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DE3143048A1 true DE3143048A1 (en) 1983-05-05
DE3143048C2 DE3143048C2 (en) 1989-10-19

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Cited By (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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2433836A1 (en) * 1974-07-15 1976-01-29 Schuelke & Mayr Gmbh DISINFECTANT WITH SPORICIDAL EFFECT

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2433836A1 (en) * 1974-07-15 1976-01-29 Schuelke & Mayr Gmbh DISINFECTANT WITH SPORICIDAL EFFECT

Cited By (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

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DE3143048C2 (en) 1989-10-19

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