NO156672B - PREPARATION WITH ANTIMICROBIAL AND ANY POSSIBLE INSECTICID EFFECT AND USE OF SUCH A PREPARATION AS A TREE AND ANTI-PROTECTIVE AGENT. - Google Patents
PREPARATION WITH ANTIMICROBIAL AND ANY POSSIBLE INSECTICID EFFECT AND USE OF SUCH A PREPARATION AS A TREE AND ANTI-PROTECTIVE AGENT. Download PDFInfo
- Publication number
- NO156672B NO156672B NO763453A NO763453A NO156672B NO 156672 B NO156672 B NO 156672B NO 763453 A NO763453 A NO 763453A NO 763453 A NO763453 A NO 763453A NO 156672 B NO156672 B NO 156672B
- Authority
- NO
- Norway
- Prior art keywords
- preparation
- aryl compound
- antimicrobial agent
- alkyl
- carbon atoms
- Prior art date
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- 230000000845 anti-microbial effect Effects 0.000 title claims description 7
- 230000000694 effects Effects 0.000 title description 5
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- -1 aryl compound Chemical group 0.000 claims description 25
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- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Description
Denne oppfinnelse angår et preparat med antimikrobiell og eventuell insekticid virkning og anvendelse av et slikt preparat som tre- og vekstbeskyttelsesmiddel. De karakteristiske trekk ved oppfinnelsen er som angitt i kravene. This invention relates to a preparation with antimicrobial and possibly insecticidal action and the use of such a preparation as a tree and growth protection agent. The characteristic features of the invention are as stated in the claims.
Formålet med foreliggende oppfinnelse er å tilveiebringe et antimikrobielt og eventuelt insekticid preparat som er effektivt mot brede grupper av mikroorganismer og, i en foretrukket ut-førelsesform, et som har lav toksisitet overfor dyre- og plante-liv. Dette formål gjennomføres i hovedsak ved å lage et preparat bestående av en disubstituert aryl-^forbindelse hvori den første bestanddel er en oleofil gruppe som er egnet til å trenge gjennom lipoidsjiktet i mikroceller og den andre bestanddelen er en hydrofil gruppe til hvilken et antimikrobielt middel er koordinert. Ved å koordinere det antimikrobielle midlet med den disubstituerte arylforbindelsen kan det observeres en synergistisk effekt hvor det er en markert økning i den mikrobielle aktiviteten til det antimikrobielle midlet, som er meget større enn det som kan tillegges med-virkningen av eventuelle antimikrobielle egenskaper hos den disubstituerte arylforbindelsen. Siden det antimikrobielle midlet er koordinert med den hydrofile substituenten, solubiliseres det antimikrobielle midlet på molekylær basis. Ved å koordinere det antimikrobielle midlet med arylforbindelsen kan det antimikrobielle midlet føres med av forbindelsen og således være i stand til å komme inn i en celle når dets beskyttelsesmembran er brudt av det kombinerte angrep av de hydrofile og oleofile substituentene i arylforbindelsen. The purpose of the present invention is to provide an antimicrobial and possibly insecticidal preparation which is effective against broad groups of microorganisms and, in a preferred embodiment, one which has low toxicity towards animal and plant life. This purpose is mainly achieved by making a preparation consisting of a disubstituted aryl compound in which the first component is an oleophilic group which is suitable for penetrating the lipoid layer in microcells and the second component is a hydrophilic group to which an antimicrobial agent is coordinated. By coordinating the antimicrobial agent with the disubstituted aryl compound, a synergistic effect can be observed where there is a marked increase in the microbial activity of the antimicrobial agent, which is much greater than what can be attributed to the contribution of any antimicrobial properties of the disubstituted the aryl compound. Since the antimicrobial agent is coordinated to the hydrophilic substituent, the antimicrobial agent is solubilized on a molecular basis. By coordinating the antimicrobial agent with the aryl compound, the antimicrobial agent can be carried by the compound and thus be able to enter a cell when its protective membrane is breached by the combined attack of the hydrophilic and oleophilic substituents in the aryl compound.
Koordinatbindingen mellom den disubstituerte arylforbindelsen og det antimikrobielle midlet kan brytes ved hjelp av konvensjonelle midler som f .eks. dannelse av en uløselig eller ikkeioniserbar forbindelse med en av de to bestanddelene i koordinatbindingen. Det er til tider ønskelig å gardere seg mot slike bindingsbrudd ved hjelp av midler som f.eks. pH-justering eller chelatering av uønskede ioner. The coordinate bond between the disubstituted aryl compound and the antimicrobial agent can be broken using conventional means such as e.g. formation of an insoluble or non-ionizable compound with one of the two constituents of the coordinate bond. It is sometimes desirable to guard against such bond breaks using means such as e.g. pH adjustment or chelation of unwanted ions.
For beskyttelse av visse substrater kan det imidlertid være ønskelig å tillate koordinatbindingen å brytes under eller etter behandling av substratet. Dette forekommer eksempelvis ved behandling av tre slik at når det en gang er avsatt i treet, endres det antimikrobielle midlet fra en vann-løselig til en vann-uløselig form, hvorved det beholder høy gjenværende aktivitet. I dette tilfelle har den opprinnelige koordinatbindingen tjent et meget nyttig formål ved å tillate det antimikrobielle midlet å avsette seg inne i og på veden på molekylbasis. For the protection of certain substrates, however, it may be desirable to allow the coordinate bond to be broken during or after treatment of the substrate. This occurs, for example, when treating wood so that once it has been deposited in the wood, the antimicrobial agent changes from a water-soluble to a water-insoluble form, whereby it retains a high residual activity. In this case, the original coordinate bond has served a very useful purpose by allowing the antimicrobial agent to deposit within and onto the wood on a molecular basis.
Den oleofile substituenten i arylforbindelsen i preparatet ifølge oppfinnelsen bør ha en grad av stereokjemisk forenelighet med strukturen i det semipermeable membranet i cellen. En vanlig struktur som opp-fyller dette kriterium er et i alt vesentlig usubstituert, rett-kjedet hydrokarbon med en lengde som er signifikant med hensyn til tykkelsen av celleveggen. Dette krever vanligvis som et minimum at alkylkjeden har omtrent seks karbonatomer eller liknende. På den annen side må ikke alkylkjeden være for lang. Siden bevegelig-hetsfriheten for en alkylkjede øker med økende kjedelengde, be-gynner alkylkjeder å rulle seg sammen dersom en viss lengde over-skrides. Når sammenrullingen er signifikant, kan det forårsake sterisk forhindring og gjøre gjennomtrengningen av celleveggen vanskelig. Mens maksimumslengden for alkylkjeden bare kan be-stemmes når det gjelder en gitt omgivelse og en spesifikk celle-struktur, antas det å være en antagelig generalisering å foreslå' The oleophilic substituent in the aryl compound in the preparation according to the invention should have a degree of stereochemical compatibility with the structure of the semipermeable membrane in the cell. A common structure that fulfills this criterion is a substantially unsubstituted, straight-chain hydrocarbon with a length that is significant with regard to the thickness of the cell wall. This usually requires as a minimum that the alkyl chain has about six carbon atoms or similar. On the other hand, the alkyl chain must not be too long. Since the freedom of movement for an alkyl chain increases with increasing chain length, alkyl chains begin to roll up if a certain length is exceeded. When the coiling is significant, it can cause steric hindrance and make penetration of the cell wall difficult. While the maximum length of the alkyl chain can only be determined in terms of a given environment and a specific cell structure, it is believed to be a reasonable generalization to suggest.
at en alkylkjede som er meget lenger enn 18 karbonatomer og mere spesielt, en som er lenger enn 24 karbonatomer, vil tape sin effektivitet når det gjelder å gjennomtrenge celleveggen. that an alkyl chain much longer than 18 carbon atoms and more particularly one longer than 24 carbon atoms will lose its effectiveness in penetrating the cell wall.
De foretrukne alkylgrupper i arylforbindelsen er ikke The preferred alkyl groups in the aryl compound are not
for forgrenede eller substituerte i slik grad at de fører til sterisk forhindring. Ikke desto mindre kan noen substituenter på hydrokarbonkjeden, som f.eks. klor, forbedre de oleofile egenskapene til den "skapte ladning" og kan med fordel brukes. Det er også observert at klor-substitusjon kan tillate bruk av kortere alkylkjeder. too branched or substituted to such an extent that they lead to steric hindrance. Nevertheless, some substituents on the hydrocarbon chain, such as e.g. chlorine, improve the oleophilic properties of the "created charge" and can be used with advantage. It has also been observed that chlorine substitution may allow the use of shorter alkyl chains.
Det kan forståes at det ikke kan gis noen fast defini-sjon når det gjelder lengde, sammensetning og konfigurasjon av den oleofile gruppen idet disse parametere nødvendigvis må justeres for de mikrobearter av bakterier og sopp som skal bekjempes. It can be understood that no fixed definition can be given in terms of length, composition and configuration of the oleophilic group, as these parameters must necessarily be adjusted for the microbial species of bacteria and fungi to be combated.
Den hydrofile bestanddelen i arylforbindelsen må være The hydrophilic component of the aryl compound must be
i stand til å danne en sterk koordinatbinding med det antimikrobielle midlet. Det er ikke for mange hydrofile substanser å velge mellom som vil koordinere godt med en substans med mirkobicide egenskaper, og to av de mest effektive og kjemisk tilgjengelige er able to form a strong coordinate bond with the antimicrobial agent. There are not too many hydrophilic substances to choose from that will coordinate well with a substance with microbicidal properties, and two of the most effective and chemically accessible are
sulfo- og hydroksylradikalene. the sulfo and hydroxyl radicals.
En foretrukket arylforbindelse er benzen som antas å A preferred aryl compound is benzene which is believed to
være mest effektiv, og kanskje i mindre grad, naftalen. Arylforbindelser bestående av mere enn to ringstrukturer kan miste sin effektivitet av mange grunner, blant dem er det faktum at deres størrelse blir stor sammenliknet med den oleofile substituenten og vil forårsake sterisk forhindring for den oleofile substituenten i å trenge gjennom mikroorganismeveggen. Selv om det ikke er av-gjørende ved praktisering av oppfinnelsen, kan sekundære substituenter på arylgruppen noen ganger vise seg ønskelige, spesielt om de er i stand til å trekke til seg elektroner for å øke styrken på koordinatbindingen mellom den hydrofile substituenten og det mikrobicide midlet. Substituenter som fungerer på denne måten er eksempelvis -NO,,, -CN og -CHO. Elektron-uttrekkende substituenter bør brukes sjelden og med forsiktighet dersom overbelastning av ringstrukturen i arylforbindelsen skal unngås. be most effective, and perhaps to a lesser extent, naphthalene. Aryl compounds consisting of more than two ring structures can lose their effectiveness for many reasons, among them the fact that their size becomes large compared to the oleophilic substituent and will cause steric hindrance for the oleophilic substituent to penetrate the microorganism wall. Although not critical to the practice of the invention, secondary substituents on the aryl group may sometimes prove desirable, particularly if they are capable of withdrawing electrons to increase the strength of the coordinate bond between the hydrophilic substituent and the microbicidal agent. . Substituents that function in this way are, for example, -NO,,, -CN and -CHO. Electron-withdrawing substituents should be used rarely and with care if overloading of the ring structure in the aryl compound is to be avoided.
Som angitt ovenfor må det antimikrobielle midlet koordinere med den hydrofile substituenten slik at det dannes en passe stabil binding dersom den skal solubiliseres og være effektiv ved utførelsen av oppfinnelsen. As indicated above, the antimicrobial agent must coordinate with the hydrophilic substituent so that a suitably stable bond is formed if it is to be solubilized and be effective in carrying out the invention.
En spesiell fordel ved oppfinnelsen ligger i det faktum at antimikrobielle midler som har kjent lav toksisitet overfor plante- og dyreliv kan gjøres mere effektive ved å sammensette dem ifølge oppfinnelsen, og således øke deres anvendbarhet.meget. Av disse midler er eksempelvis metallchelatene av 8- kino- A particular advantage of the invention lies in the fact that antimicrobial agents which have known low toxicity towards plants and animals can be made more effective by compounding them according to the invention, thus greatly increasing their applicability. Of these agents, for example, the metal chelates of 8-kino-
linol (oksin) ganske betydningsfulle, spesielt kobber-8-kinolinolat (heretter kalt "Cu-8-Q"). Den følgende liste er tatt fra littera-turreferanser om den relative effektiviteten av forskjellige metall-kinolinolater i synkende aktivitetsrekkefølge: linol (oxine) quite significant, especially copper-8-quinolinolate (hereafter called "Cu-8-Q"). The following list is taken from literature references on the relative effectiveness of various metal quinolinolates in descending order of activity:
kvikksølv Mercury
kobber copper
kadmium cadmium
nikkel nickel
bly lead
kobolt cobalt
sink zinc
jern iron
kalsium. calcium.
Aluminium og tinn har også vist seg anvendbare. Aluminum and tin have also proven useful.
Andre grupper av forbindelser som er funnet å være effektive som antimikrobielle midler når de koordineres med substituerte arylpreparater , er imidazolene og tiazolene. Other groups of compounds found to be effective as antimicrobial agents when coordinated with substituted aryl compounds are the imidazoles and thiazoles.
En med spesielt god mikrobicid aktivitet er et benzimidazol som markedsføres av Riedel-de-Haen AG, Seelze/Hanover, BRD, under sin produktbetegnelse "Mergal BCM", som antas å være 2-(metoksykarba-moyl)-benzimidazol. One with particularly good microbicidal activity is a benzimidazole marketed by Riedel-de-Haen AG, Seelze/Hanover, BRD, under its product name "Mergal BCM", which is believed to be 2-(methoxycarba-moyl)-benzimidazole.
Følgende eksempler gis for å vise effektiviteten av et av de foretrukne mirkobicide preparater ifølge oppfinnelsen hvor dodecylbenzen-sulfonsyre (DDBSA) velges som den disubstituerte arylforbindelsen og Cu-8-Q velges som mikrobicid. Den oleofile substituenten på benzenringen i DDBSA er alkylkjeden med 12 karbonatomer (omtrent) og den hydrofile substituenten er sulfogruppen. Den oleofile hydrokarbonkjeden på DDBSA er i hovedsak en tetramer av propylen og vil vanligvis variere, slik den er kommersielt tilgjengelig, fra mellom 11 og 13 karbonatomer. Mesteparten av DDBSA som er ålment tilgjengelig er rett-kjedet, men noe er forgrenet (såkalt "myk" og"hård" DDBSA), og begge har vist seg effektive i preparatet ifølge oppfinnelsen. The following examples are given to show the effectiveness of one of the preferred microbicidal preparations according to the invention where dodecylbenzenesulfonic acid (DDBSA) is chosen as the disubstituted aryl compound and Cu-8-Q is chosen as the microbicide. The oleophilic substituent on the benzene ring in DDBSA is the alkyl chain with 12 carbon atoms (approximately) and the hydrophilic substituent is the sulfo group. The oleophilic hydrocarbon chain of DDBSA is essentially a tetramer of propylene and will typically range, as commercially available, from between 11 and 13 carbon atoms. Most of the DDBSA that is widely available is straight-chain, but some is branched (so-called "soft" and "hard" DDBSA), and both have proven effective in the preparation according to the invention.
Det Cu-8-Q som brukes i eksemplene fremstilles ved reaksjon mellom 8-hydroksy-kinolinol og en kobberforbin som f.eks. kobberhydrat (kuprihydroksyd). The Cu-8-Q used in the examples is produced by reaction between 8-hydroxyquinolinol and a copper phorbin such as e.g. copper hydrate (cupric hydroxide).
Et fortynningsmiddel brukes med blandingen av DDBSA og Cu-8-Q som ikke bare tjener som et viskositets-reduserende middel, men også, antas det, tillater ionisering av alkylbenzensulfonsyren slik at det oppnås fullstendig solubilitet av forbindelsen. Det er funnet at fullstendig solubilisering gjennom- A diluent is used with the mixture of DDBSA and Cu-8-Q which not only serves as a viscosity-reducing agent, but also, it is believed, allows ionization of the alkylbenzenesulfonic acid to achieve complete solubility of the compound. It has been found that complete solubilization through-
føres lettest ved bruk av høypolare organiske løsningsmidler som er blandbare med vann. En særskilt liste med passende fortynningsmidler for anvendelse i foreliggende oppfinnelse er oppført nedenfor : is carried out most easily by using highly polar organic solvents that are miscible with water. A separate list of suitable diluents for use in the present invention is listed below:
Metanol Methanol
Etanol Ethanol
Isopropanol Isopropanol
n-Butanol n-Butanol
Dimetylformamid Dimethylformamide
N/metyl-2-pyrrolidon N/methyl-2-pyrrolidone
Etylen-glykol Ethylene glycol
Vann Water
Propylen-glykol Propylene glycol
Stoddard løsningsmiddel Stoddard solvent
Toluen Toluene
Generelt er det foretrukket å anvende fra 5 til 50 vektdeler DDBSA og 1 til 50 vektdeler polart løsningsmiddel for hver vektdel metall-8-kinolinolat. Det mest foretrukne preparat ifølge oppfinnelsen inneholder fra 2 til 10 vektdeler Cu-8-Q, 25 til 83 vektdeler alkylbenzensulfonsyre og 15 til 35 vektdeler fortynningsmiddel pr. 100 vektdeler av konsentratet. Et spesielt preparat fremstilt ifølge oppfinnelsen inneholder ca. 5 vektdeler Cu-8-Q, ca. 64 vektdeler DDBSA og ca. 31 vektdeler metanol. I tillegg er det funnet nyttig å tilsette mindre mengder, f.eks. 5 vekt%, etylen-glykol for å forbedre holdbarheten. In general, it is preferred to use from 5 to 50 parts by weight of DDBSA and 1 to 50 parts by weight of polar solvent for each part by weight of metal 8-quinolinolate. The most preferred preparation according to the invention contains from 2 to 10 parts by weight of Cu-8-Q, 25 to 83 parts by weight of alkylbenzenesulfonic acid and 15 to 35 parts by weight of diluent per 100 parts by weight of the concentrate. A special preparation produced according to the invention contains approx. 5 parts by weight Cu-8-Q, approx. 64 parts by weight DDBSA and approx. 31 parts by weight methanol. In addition, it has been found useful to add smaller quantities, e.g. 5% by weight, ethylene glycol to improve durability.
En metode for fremstilling av preparatene ifølge oppfinnelsen er å blande fortynningsmidlet med DDBSA or røre inn kinolinolatet. Blandingen kan ledsages av frigjøring av eksoterm-isk reaksjonsvarme som gjør at alle bestanddeler oppløses raskere. One method for producing the preparations according to the invention is to mix the diluent with DDBSA or stir in the quinolinolate. The mixture may be accompanied by the release of exothermic heat of reaction which causes all components to dissolve more quickly.
En annen egnet fremgangsmåte for fremstilling av konsentratet består i først å omsette kobberhydroksyd med en blanding av metanol og DDBSA slik at det dannes et metallsalt. Så innrøres 8-hydroksy-kinolin slik at metallchelatet dannes. Another suitable method for producing the concentrate consists in first reacting copper hydroxide with a mixture of methanol and DDBSA so that a metal salt is formed. Then 8-hydroxyquinoline is stirred in so that the metal chelate is formed.
Konsentratene som er fremstilt som ovenfor angitt, fortynnes, fortrinnsvis med vann, før bruk og kan faktisk fortynnes etter behov. Andre fortynningsmidler kan brukes og omfatter xylen, isopropanol, etylenglykol og nafta. De fortynnede løsningene kan påføres ved kjente teknikker, som f.eks. med pensel, sprøyting, dypping eller gnidning. The concentrates prepared as indicated above are diluted, preferably with water, before use and can actually be diluted as needed. Other diluents can be used and include xylene, isopropanol, ethylene glycol and naphtha. The diluted solutions can be applied by known techniques, such as e.g. by brushing, spraying, dipping or rubbing.
I de eksempler som følger ble effektiviteten av de forskjellige sammensetningene bestemt ved å behandle nyskårne furu-bord ved dyppenedsenkning i 10 sekunder i det preparat som skal testes. Bordene ble plassert, sammen med en ubehandlet kontroll, In the examples that follow, the effectiveness of the different compositions was determined by treating freshly cut pine boards by immersion for 10 seconds in the preparation to be tested. The tables were placed, along with an untreated control,
i et kammer i den angitte tidsperiode og holdt ved en temperatur av ca. 27°C og en fuktighet av ca. 70%. in a chamber for the specified time period and kept at a temperature of approx. 27°C and a humidity of approx. 70%.
Når bordene ble fjernet fra kammeret, ble de visuelt sammenliknet med kontrollen. Resultatene av effektivitetstesten av fungicidet uttrykkes som den prosent av bordets totale over-flateareale som er dekket av flekker og mugg. Jo lavere prosent-tall, jo bedre er således aktiviteten som fungicid. When the boards were removed from the chamber, they were visually compared to the control. The results of the fungicide effectiveness test are expressed as the percentage of the table's total surface area covered by stains and mold. The lower the percentage, the better the activity as a fungicide.
Alle deler som er angitt i eksemplene er vektdeler. All parts given in the examples are parts by weight.
Eksempler Examples
Eksempler I til III. Examples I to III.
For å fastslå de egne fungicide egenskapene for Cu-8-Q ble det oppløst i en sterk mineralsyre og i maleinsyre og resultatene ble sammenliknet med en løsning med liknende Cu-8-Q-konsentrasjon laget ifølge oppfinnelsen. Hvert eksempel ble fortynnet 1:400 med vann for anvendelse. To determine the specific fungicidal properties of Cu-8-Q, it was dissolved in a strong mineral acid and in maleic acid and the results were compared with a solution with a similar Cu-8-Q concentration made according to the invention. Each sample was diluted 1:400 with water for use.
Som det kan sees er oppløsning av Cu-8-Q i svovelsyre og maleinsyre ikke på langt nær så effektivt som å solubilisere det med en disubstituert arylforbindelse . As can be seen, dissolving Cu-8-Q in sulfuric and maleic acids is not nearly as effective as solubilizing it with a disubstituted aryl compound.
Eksempel IV til VIII. Examples IV to VIII.
I disse eksempler ble Cu-8-Q oppløst i forbindelser som er nær beslektet med DDBSA bortsett fra at de ikke hadde den oleofile substituent eller "skapte ladning" som beskrevet i denne søknad. In these examples, Cu-8-Q was dissolved in compounds closely related to DDBSA except that they did not have the oleophilic substituent or "created charge" as described in this application.
I de følgende eksempler IV til VIII gjelder de data som er gitt i tabellen, for konsentratet. I alle tilfeller ble dette konsentrat fortynnet med 400 deler vann pr. 1 del konsentrat før behandling av testgjenstanden. In the following examples IV to VIII, the data given in the table apply to the concentrate. In all cases, this concentrate was diluted with 400 parts of water per 1 part concentrate before processing the test object.
Fra det foranstående kan det sees at forbindelser dannet ved substitusjon av en sulfongruppe på en ellers usubstituert arylforbindelse er ganske ineffektive som fungicider. En viss forbedring kan noteres ved i tillegg å substituere en metylgruppe, men den mest dramatiske forbedring noteres om den andre substituenten er en alkylgruppe med 12 karbonatomer, som er en oleofilt skapt ladning innenfor oppfinnelsens omfang. Tridecylbenzensulfon-syre vist seg også å være meget effektiv. Imidlertid viste 4-dodecylert oksydibenzen-sulfonsyre seg å være mindre effektiv selv om den anses nyttig i visse tilfeller. From the foregoing it can be seen that compounds formed by substitution of a sulfone group on an otherwise unsubstituted aryl compound are quite ineffective as fungicides. A certain improvement can be noted by additionally substituting a methyl group, but the most dramatic improvement is noted if the second substituent is an alkyl group with 12 carbon atoms, which is an oleophilic charge within the scope of the invention. Tridecylbenzenesulfonic acid has also been shown to be very effective. However, 4-dodecylated oxydibenzenesulfonic acid proved to be less effective although it is considered useful in certain cases.
Eksempler IX til XI. Examples IX to XI.
For å bevise effektiviteten til et fungicid som er fremstilt ifølge oppfinnelsen ble preparatet fra eksempel IV fortynnet 1:200 med vann og behandlede bord ble sammenliknet med bord som var behandlet med tre av de standard-fungicidpreparater som nå er vanlig brukt. To prove the effectiveness of a fungicide produced according to the invention, the preparation from example IV was diluted 1:200 with water and treated tables were compared with tables that had been treated with three of the standard fungicide preparations that are now commonly used.
I motsetning til det foranstående oppviste kontrollen som var behandlet med preparatet fra eksempel IV 17% flekker og In contrast to the above, the control which had been treated with the preparation from example IV showed 17% spots and
mugg i test 1 og 0% i test 2. mold in test 1 and 0% in test 2.
Eksempel XII. Example XII.
Følgende preparat ble fremstilt ifølge den tidligere angitte teknikk: The following preparation was prepared according to the previously stated technique:
Dette preparat ble fortynnet med vann og testet i sammen-likning med natriumtetraklorfenat (23%) flytende konsentrat som også ble fortynnet med vann, på virkning mot organismer på tre arter av friskt tømmer -- Douglas-gran, Ambilis-gran og Ponderosa-furu . Organismene var: This preparation was diluted with water and tested in comparison with sodium tetrachlorophenate (23%) liquid concentrate which was also diluted with water, for activity against organisms on three species of fresh timber -- Douglas fir, Ambilis fir and Ponderosa pine . The organisms were:
Nyskårede vedprøver ble dyppebehandlet (15 sekunders ned-dykning) med testfungicidene og så inokulert med sporesuspensjoner av de ovenfor beskrevne fungi. Testbordene pluss ubehandlede kon-trollbord ble så plassert i et varmt, fuktig kammer i fire uker. Resultatene er oppført i nedenstående tabell hvor: Freshly cut wood samples were dip-treated (15 second immersion) with the test fungicides and then inoculated with spore suspensions of the fungi described above. The test boards plus untreated control boards were then placed in a warm, humid chamber for four weeks. The results are listed in the table below where:
Klorfenolpreparatet ovenfor er typisk for den type sorti anvendes for bekjempelse av saftfarging og -mugg i friskt tømmer. Når det gjelder de testede tresorter kan det imidlertid bemerkes at klorfenol-typene viser dårlig bekjempelse av C. fragrans, og som resultat derav er det vanlig å bruke kvikksølv-baserte fungicider (som f.eks. fenylmerkuriacetat) i kombinasjon med klorfenolen for å oppnå ønsket bekjempelse. Preparatet fra eksempel XII opp-• viste imidlertid overlegen bekjempelse av C. fragrans. The chlorophenol preparation above is typical of the type of variety used to combat sap staining and mold in fresh timber. Regarding the tested tree species, however, it can be noted that the chlorophenol types show poor control of C. fragrans, and as a result it is common to use mercury-based fungicides (such as phenyl mercuric acetate) in combination with the chlorophenol to achieve desired combat. However, the preparation from example XII up-• showed superior control of C. fragrans.
Eksempler XIII til XVII. Examples XIII to XVII.
For å demonstrere de fungicide egenskapene for forskjellige metall-8-kinolinolater ble løsninger fremstilt ved å bruke 5 deler av de angitte metall-8-kinolinolater, 64 deler DDBSA og 31 deler metanol. To demonstrate the fungicidal properties of various metal 8-quinolinolates, solutions were prepared using 5 parts of the indicated metal 8-quinolinolates, 64 parts DDBSA and 31 parts methanol.
De foranstående metall-8-kinolinolater kan også fremstilles ved i situ-reaksjon av oksin med et passende metall i. DDBSA/metanol-reaksjonsmediet. The above metal 8-quinolinolates can also be prepared by in situ reaction of oxine with a suitable metal in the DDBSA/methanol reaction medium.
Eksempel XVIII. Example XVIII.
Et fungicid preparat med Cu-8-Q ble fremstilt ved anvendelse av substituerte arylforbindelser av alkylfenoltypen for å demonstrere effektiviteten av erstatning av sulfogruppen med en hydroksylgruppe som hydrofil substituent ved utførelsen av opp- A fungicidal preparation with Cu-8-Q was prepared using substituted aryl compounds of the alkylphenol type to demonstrate the effectiveness of replacing the sulfo group with a hydroxyl group as a hydrophilic substituent in the performance of up-
Den ovenstående blanding av ingredienser ble oppvarmet ved 82°C inntil oppløsningen av Cu-8-Q, fremstilt i situ, var fullstendig. Dette preparats innhold av Cu-8-Q ble så redusert fra 5 til 0,25% ved fortynning med mineralsprit. The above mixture of ingredients was heated at 82°C until the dissolution of Cu-8-Q, prepared in situ, was complete. This preparation's content of Cu-8-Q was then reduced from 5 to 0.25% by dilution with mineral spirits.
Bomullslerretstøy (283 g) ble behandlet til ikke mere ble opptatt av testløsningen ved neddykking i løsningen, tøyet ble tørket og neddykket i sauegjødsel mettet med vann. Samtidig ble kontrolltøy også neddykket, så vel som tøy behandlet med et kommersielt Cu-8-Q preparat ("Cunilate 2174"), solubilisert i nikkel-acetat og 2-etylheksoinsyre inneholdende 0,25% Cu-8-Q i en mineralsprit-bærer. Ved slutten av 28 dager ved 24°C ble tøyet fjernet fra sauegjødselen, vasket og undersøkt på styrketap med følgende resultater: Cotton linen dish cloth (283 g) was treated until no more was taken up by the test solution when immersed in the solution, the cloth was dried and immersed in sheep manure saturated with water. At the same time, control clothes were also immersed, as well as clothes treated with a commercial Cu-8-Q preparation ("Cunilate 2174"), solubilized in nickel acetate and 2-ethylhexoic acid containing 0.25% Cu-8-Q in mineral spirits. carries. At the end of 28 days at 24°C, the fabric was removed from the sheep manure, washed and examined for strength loss with the following results:
Eksempel XIX. Example XIX.
En annen test-evaluering illustrerer den betydelige effektiviteten for preparatet fra eksempel XVIII mot Lenzites trabea, en utbredt sopp som forårsaker destruktivt treforfall, spesielt på steder over jorden hvor meget få typer av sopp kan mot-stå de høye temperaturer som forekommer. Testmetoden som anvendes er en industristandardmetode -- National Woodwork Manufacturers' Association M-l-70 Soil Block Test. Den består i å behandle, ved impregnering til metning, av Ponderosa-furublokker med testfungi-cidløsningen i en toluenbærer. Etter tørking underkastes blokkene en kraftig vannutlutningsfremgangsmåte, hvoretter blokken tørkes igjen og inokuleres med en Lenzites trabea sopp-kultur. Ved slutten av testperioden måles vekttapet som angir graden av forfall hos treet. Another test evaluation illustrates the significant effectiveness of the preparation of Example XVIII against Lenzites trabea, a widespread fungus that causes destructive wood decay, especially in places above ground where very few types of fungi can withstand the high temperatures that occur. The test method used is an industry standard method -- the National Woodwork Manufacturers' Association M-l-70 Soil Block Test. It consists in treating, by impregnation to saturation, Ponderosa pine blocks with the test fungicide solution in a toluene carrier. After drying, the blocks are subjected to a vigorous water leaching process, after which the block is dried again and inoculated with a Lenzites trabea fungus culture. At the end of the test period, the weight loss is measured, which indicates the degree of decay in the tree.
Det er ganske klart at preparatet ifølge oppfinnelsen i denne testen skaffer overlegen beskyttelse av veden. It is quite clear that the preparation according to the invention provides superior protection for the wood in this test.
Xylen, benzen, toluen, Stoddard løsningsmiddel, tunge petroleumoljer og naftaer er egnet for fortynning av denne klasse av preparater ifølge oppfinnelsen. Vanligvis gir løsningsmidler med høyere aromatisitet bedre løsningsstabilitet, dvs. ingen ut-feining av Cu-8-Q. Større løsnings-stabilitet oppnås ved å øke forholdet mellom alkylfenol og Cu-8-Q og/eller ved å øke forholdet mellom alkylfenol/Cu-8-Q-preparat og petroleumløsningsmiddel og/ eller fortynningsmiddel. Xylene, benzene, toluene, Stoddard solvent, heavy petroleum oils and naphthas are suitable for diluting this class of preparations according to the invention. Generally, solvents with higher aromaticity provide better solution stability, i.e. no stripping of Cu-8-Q. Greater solution stability is achieved by increasing the ratio between alkylphenol and Cu-8-Q and/or by increasing the ratio between alkylphenol/Cu-8-Q preparation and petroleum solvent and/or diluent.
Vanligvis foretrekkes de alkylfenoler som er flytende Generally, those alkylphenols which are liquid are preferred
ved romstemperatur, spesielt nonyl- og dodecylfenol på grunn av lav pris og kommersiell tilgjengelighet. at room temperature, especially nonyl and dodecylphenol due to low price and commercial availability.
For å meddele vannfrastøtende egenskaper til denne klasse preparater kan voks og visse harpikser, omfattende visse silikon- og kolofoniumesterharpikser, innblandes, så vel som andre midler som er kjente på området. To impart water-repellent properties to this class of compositions, waxes and certain resins, including certain silicone and rosin master resins, may be incorporated, as well as other agents known in the art.
Eksempler XX til XXII. Examples XX to XXII.
For å demonstrere den meget reelle synergistiske effekt av preparatet ifølge oppfinnelsen ble Cu-8-Q og DDBSA To demonstrate the very real synergistic effect of the preparation according to the invention, Cu-8-Q and DDBSA were
testet hver for seg og i kombinasjon for å bestemme deres effektivitet når det gjelder å bekjempe mugg og saftfarging på nyhugget tømmer. tested individually and in combination to determine their effectiveness in combating mold and sap staining on freshly cut timber.
Eksempler XXIII til XXIX. Examples XXIII to XXIX.
Som ytterligere bevis, på effektiviteten av antimikrobielle preparater ifølge oppfinnelsen, ble det utført en rekke tester ved utnyttelse av DDBSA som den substituerte arylforbindelsen ifølge oppfinnelsen koordinert med de nedenfor oppførte antimikrobielle midler. En 1:200 anvendelsesfortynning med vann ble fremstilt fra konsentrater som inneholdt 65 deler DDBSA, 30 deler metanol og 5 deler av det antimikrobielle midlet. Nyskårne, ferske furutestbord ble dyppe-behandlet og bedømt på farge og mugg etter 30 dager i det foran nevnte testkammer med konstant atmos-fære : As further proof of the effectiveness of the antimicrobial preparations according to the invention, a series of tests were carried out utilizing DDBSA as the substituted aryl compound according to the invention coordinated with the antimicrobial agents listed below. A 1:200 application dilution with water was prepared from concentrates containing 65 parts DDBSA, 30 parts methanol and 5 parts of the antimicrobial agent. Freshly cut, fresh pine test tables were dip-treated and assessed for color and mold after 30 days in the aforementioned test chamber with a constant atmosphere:
I noen tilfeller kan det vise seg fordelaktig å innblande andre antimikrobielle midler i et gitt preparat for å øke total-spektret for den antimikrobielle aktiviteten. Slike tillegg av antimikrobielle midler behøver ikke nødvendigvis være av den type som hittil er beskrevet i dette patent. Når eksempelvis friskt tømmer behandles for å hindre dannelse av saftfarging eller mugg, er det noen ganger ønskelig for å oppnå bredere beskyttelse å innblande en klorfenol som f.eks. pentaklorfenol, tetraklorfenol eller 2,4,5-triklorfenol, i preparatene ifølge oppfinnelsen. Det ligger også innenfor oppfinnelsens omfang å innblande insekticider. Det er overraskende funnet at når et antall vel kjente insekticider tilsettes til vann-løselige preparater ifølge oppfinnelsen, så solubiliseres insekticidet og forblir solubilisert når preparatet fortynnes med vann før bruk. Insekticider som viser slike uvanlig oppførsel omfatter: 0,O-Dimety1-S-(1,2-dikarbetoksyetyl)fosforditionat; In some cases, it may prove advantageous to mix other antimicrobial agents into a given preparation in order to increase the total spectrum of the antimicrobial activity. Such additions of antimicrobial agents do not necessarily have to be of the type described so far in this patent. When, for example, fresh timber is treated to prevent the formation of sap staining or mould, it is sometimes desirable to achieve wider protection by mixing in a chlorophenol such as e.g. pentachlorophenol, tetrachlorophenol or 2,4,5-trichlorophenol, in the preparations according to the invention. It is also within the scope of the invention to include insecticides. It has surprisingly been found that when a number of well-known insecticides are added to water-soluble preparations according to the invention, the insecticide is solubilized and remains solubilized when the preparation is diluted with water before use. Insecticides exhibiting such unusual behavior include: 0,O-Dimethyl-S-(1,2-dicarbethoxyethyl)phosphorus dithionate;
1,2,4,5,6,7,8,8-Oktaklor-2,3,3a,4,7,7a-heksahydro-4,7-metanoindan; 1,2,4,5,6,7,8,8-Octachloro-2,3,3a,4,7,7a-hexahydro-4,7-methanoindane;
1,1,1-Triklor-2,2-bis(p-metoksyfenyl)etanol; og 1-nafty1-N-metylkarbamat. 1,1,1-Trichloro-2,2-bis(p-methoxyphenyl)ethanol; and 1-naphthy1-N-methylcarbamate.
Disse meget brukte insekticider har hittil bare vært tilgjengelige i ikke-vannløselige former som f.eks. støv, fuktbare pulvere og emulgerbare konsentrater. Tilgjengelighet som virkelige vannløs-ninger byr på betydelige fordeler ved håndtering, blanding, stabi-litet og påførings jevnhet. These widely used insecticides have so far only been available in non-water-soluble forms such as e.g. dust, wettable powders and emulsifiable concentrates. Availability as real water solutions offers significant advantages in handling, mixing, stability and uniformity of application.
Eksempel XXXII. Example XXXII.
Noen av preparatene ifølge oppfinnelsen oppviser uventet insekticid aktivitet når de sammenliknes med konvensjonelle, solu-biliserte Cu-8-Q-preparater og når de sammenliknes med et kjent insekticid (pentaklorfenol). Mot termitter i en jordbegravelse-test i Memphis, Tennessee, ble følgende preparater bedømt: a) Eksempel XII, fortynnet med vann til et Cu-8-Q-innhold på 0,25%; b) Eksempel XVIII, fortynnet med mineralsprit til et Cu-8-Q-innhold på 0,25%; c) "Cunilate 2174", fortynnet med mineralsprit til et Cu-8-Q-innhold på 0,25% og d) En 5,0%-ig pentaklorfenol-løsning i mineralsprit inneholdende 4% propylenglykoleter for å skaffe tilstrekkelig Some of the preparations according to the invention exhibit unexpected insecticidal activity when compared with conventional, solubilized Cu-8-Q preparations and when compared with a known insecticide (pentachlorophenol). Against termites in a soil burial test in Memphis, Tennessee, the following preparations were evaluated: a) Example XII, diluted with water to a Cu-8-Q content of 0.25%; b) Example XVIII, diluted with mineral spirits to a Cu-8-Q content of 0.25%; c) "Cunilate 2174", diluted with mineral spirits to a Cu-8-Q content of 0.25% and d) A 5.0% pentachlorophenol solution in mineral spirits containing 4% propylene glycol ether to provide sufficient
pentaklorfenol-solubilitet og hinder sublimering fra veden. pentachlorophenol solubility and hinder sublimation from the wood.
Tørre sydlige, gule furustaver, 1,86 cm x 1,86 cm i tversnitt og 60cm lange, ble dyppeimpregnert med testløsningene, fikk tørke i en uke og ble så begravet til en dybde av 30 cm i jorden i 15 måneder, ved hvilket tidspunkt disse resultater ble observert: Dry southern yellow pine sticks, 1.86 cm x 1.86 cm in cross-section and 60 cm long, were dip-impregnated with the test solutions, allowed to dry for one week, and then buried to a depth of 30 cm in the soil for 15 months, at which time these results were observed:
Begge preparater ifølge oppfinnelsen oppviste termitt-bekjempelse i hovedsak lik den til pentaklorfenolløsningen og av-gjort overlegen overfor begge de ubehandlede kontrollstavene og de Both preparations according to the invention showed termite control essentially equal to that of the pentachlorophenol solution and decidedly superior to both the untreated control sticks and the
som var behandlet med "Cunilate 2174" . which had been treated with "Cunilate 2174".
Eksempel XXXIII. Example XXXIII.
Det nedenfor oppførte preparat ble fremstilt ifølge tidligere beskrevne fremgangsmåter: The preparation listed below was prepared according to previously described procedures:
Når det ble bedømt som germicid ved A.O.A.C. Use Dilution Method (12te utg., 1975), anvendt fortynnet med vann, 10 ring-bærere pr. organisme (inkubert ved 27°C i 48 timer), ble de resultater som er oppført i nedenstående tabell oppnådd etter 10 minutters kontakttid ved 20°C. I tabellen er A = subkultur og B = resubkultur. When it was rated as a germicide by the A.O.A.C. Use Dilution Method (12th ed., 1975), used diluted with water, 10 ring carriers per organism (incubated at 27°C for 48 hours), the results listed in the table below were obtained after 10 minutes of contact time at 20°C. In the table, A = subculture and B = resubculture.
Den beregnede akutte ld^q for det foranstående preparat før fortynning med vann for bruk er 4160 mg pr. kg kroppsvekt (rotte, oral administrasjon). Et 10-minutters drap kreves av E.P.A. mot de første tre patogener for salg som hospital-germicid. Den fjerde organismen er hovedårsaken til slim i resirkulerte kjølevannsystemer og masse- og papirfabrikker, hvorved anvendbar-heten av preparatet som slimicid indikeres. The calculated acute ld^q for the above preparation before dilution with water for use is 4160 mg per kg body weight (rat, oral administration). A 10-minute kill is required by the E.P.A. against the first three pathogens for sale as a hospital germicide. The fourth organism is the main cause of slime in recycled cooling water systems and pulp and paper mills, whereby the applicability of the preparation as a slimicide is indicated.
Eksempel XXXIV. Example XXXIV.
Ved å bruke godtatte A.O.A.C.-metoder for soppbedømmelse ble preparatet fra eksempel XXXIII bedømt som fungicid mot Aspergillus niger (en utbredt svart mugg) og Trichophyton mentagrophytes (kjent som årsak til fotsopp): Aspergillus niger - 1:200 anvendelsesfortynning i destillert vann - ingen vekst etter 10 minutters ekspon-er ing , Using accepted A.O.A.C. methods of fungal assessment, the preparation of Example XXXIII was assessed as fungicidal against Aspergillus niger (a widespread black mold) and Trichophyton mentagrophytes (known to cause athlete's foot): Aspergillus niger - 1:200 application dilution in distilled water - no growth after 10 minutes of exposure,
E.P.A. = United States Environmental protection Agency E.P.A. = United States Environmental Protection Agency
Trichophyton mentagrophytes - 1:750 anvendelsesfortynning i destillert vann - ingen vekst etter 10 minutters eksponering. Trichophyton mentagrophytes - 1:750 application dilution in distilled water - no growth after 10 minutes exposure.
Liknende resultater oppnås ved å anvende sink-8-kino-linolat eller aluminium-8-kinolinolat i preparatet i dette eksempel; sinkoksyd og aluminiumhydroksyd omsettes respektive med 8-hydroksykinolin istedetfor kobberhydrat. Similar results are obtained by using zinc 8-quinolinolate or aluminum 8-quinolinolate in the preparation in this example; zinc oxide and aluminum hydroxide are reacted respectively with 8-hydroxyquinoline instead of copper hydrate.
Eksempel XXXV. Example XXXV.
Preparatet ble fremstilt ifølge den allerede beskrevne metode og bedømt på effektivitet overfor cilierte protozoer og to typer virus med disse resultater: The preparation was prepared according to the already described method and assessed for effectiveness against ciliated protozoa and two types of virus with these results:
Hemaqlutineringsforsøk Haemagglutination test
HA-titeren er et mål på antallet smittsomme viruspartikler som foreligger i test-suspensjonen. The HA titer is a measure of the number of infectious virus particles present in the test suspension.
Belegg- forsøk., Coating test.,
Via samme fremgangsmåte som ovenfor inneholdt de ubehandlede virus-suspensjoner 6,4 x 10^ pfu/ml Newcastle-sykdom-viruspartikler respektive. Etter behandling med de 1:50 og 1:200 anvendelsesfortynningen ble det oppnådd avlesninger på 0 pfu/ml. Hver pfu representerer en smittsom viruspartikkel. En null pfu-avlesning representerer total inaktivering av det sittsomme birus. Via the same procedure as above, the untreated virus suspensions contained 6.4 x 10^ pfu/ml Newcastle disease virus particles respectively. After treatment with the 1:50 and 1:200 application dilutions, readings of 0 pfu/ml were obtained. Each pfu represents an infectious virus particle. A zero pfu reading represents total inactivation of the resident virus.
Inhiberinq av protozoer. Inhibition of protozoa.
Inhibering av vekst av cilierte protozoer (Tetrahymena) Inhibition of growth of ciliated protozoa (Tetrahymena)
•i damvann ble oppnådd ved en 6 ppm konsentrasjon av testpreparatet etter 6 timers og 72 timers kontakttider. Avlesningen på 6 ppm representerer MIC (Minimum inhiberingskonsentrasjon). • in pond water was achieved at a 6 ppm concentration of the test preparation after 6 hour and 72 hour contact times. The reading of 6 ppm represents the MIC (Minimum Inhibitory Concentration).
Disse data illustrerer den store effektiviteten til preparatet mot de testede mikroorganismer. These data illustrate the great effectiveness of the preparation against the tested microorganisms.
Eksempel XXXVI. Example XXXVI.
Preparatene ifølge oppfinnelsen bekjemper en rekke plante- og avlingssykdommer, som illustrert ved bruk av følgende preparat: The preparations according to the invention combat a number of plant and crop diseases, as illustrated by the use of the following preparation:
A. Valencia- appelsiner. A. Valencia oranges.
Testet på høstet frukt mot Phomosis stilk-enderåte og Diplodisråte i en 1:100 bruksfortynning i vann, 2 minutters dyppe-applisering. Etter 3 uker ved 21°C ble følgende prosentødeleggelse notert: Kontroll- (ubehandlede) appelsiner - 9,5% ødeleggelse Behandlede appelsiner - 5,3% ødeleggelse Tested on harvested fruit against Phomosis stem end rot and Diplodis rot in a 1:100 use dilution in water, 2 minute dip application. After 3 weeks at 21°C the following percent destruction was noted: Control (untreated) oranges - 9.5% destruction Treated oranges - 5.3% destruction
B. Sukker- rør. B. Cane sugar.
En agar-kimtest mot Ceratocystis paradoxa (forårsaker rate ved frøbitene) i en 1:10000 (100 ppm) anvendelsesfortynning i vann. Ved 100 ppm konsentrasjon oppnåddes en 3,0 mm inhiberings-sone. An agar germ test against Ceratocystis paradoxa (causes rate at the seed pieces) in a 1:10000 (100 ppm) application dilution in water. At 100 ppm concentration, a 3.0 mm inhibition zone was obtained.
C. Ferskentrær. C. Peach trees.
Testet mot Taphrina deformans (forårsaker bladkrølle-sykdom). Fire test-trær ble sprøytet to ganger med to ukers mellomrom med en 1:400 bruksløsning i vann. Tre måneder senere ble 100 blader på hvert tre bedømt på bladkrølling: Behandlede blader 13,5% bladkrølling Kontroll- (ubehandlede) blader 100% bladkrølling Tested against Taphrina deformans (causes leaf curl disease). Four test trees were sprayed twice at two-week intervals with a 1:400 application solution in water. Three months later, 100 leaves on each tree were assessed for leaf curl: Treated leaves 13.5% leaf curl Control (untreated) leaves 100% leaf curl
D. Bomull. D. Cotton.
Effektivitet mot seks sopper og en bakterie (Xanthomonas malvecearum) som er forbundet med sykdommer på bomullsfrø eller Efficacy against six fungi and one bacterium (Xanthomonas malvecearum) associated with diseases of cottonseed or
-frøplanter og andre planter ble bedømt i vitro, ved bruk av følgende preparater, og / r 2: -seedlings and other plants were assessed in vitro, using the following preparations, and / r 2:
Begge preparater ble fremstilt ifølge fremgangsmåter som er beskrevet i tidligere eksempler. Both preparations were prepared according to methods described in previous examples.
Følgende resultater ble oppnådd uttrykt som ppm av testpreparat i vann og den relative vekstinhibering oppnådd ved hver teststyrke på hver testet organisme. I tabellen nedenfor er: The following results were obtained expressed as ppm of test preparation in water and the relative growth inhibition achieved at each test strength on each tested organism. In the table below are:
0 = ingen synlig inhibering 0 = no visible inhibition
1 = noen inhibering 1 = some inhibition
2 = betydelig inhibering (liten vekst) 2 = significant inhibition (small growth)
3 = total inhibering (ingen vekst) 3 = total inhibition (no growth)
Det ligger innenfor oppfinnelsesomfanget å modifisere de beskrevne preparater for å forbedre ytelsen eller forandre fysi-kalske egenskaper for å oppfylle de krav på spesifikke sluttan-vendelser. F. eks. kan det, i tillegg til variering av de relative mengder av brukte materialer, gjøres modifikasjoner for spesielle anvendelser ved å tilsette tiksotropiske midler, rensemidler, detergenter, smussbærende midler, filmdannende midler og andre anvendbare additiver. It is within the scope of the invention to modify the described preparations to improve performance or change physical properties in order to meet the requirements for specific end-uses. For example in addition to varying the relative amounts of materials used, modifications can be made for particular applications by adding thixotropic agents, cleaning agents, detergents, soil-carrying agents, film-forming agents and other applicable additives.
Ved høye anvendelseskonsentrasjoner oppviser noen av preparatene ifølge oppfinnelsen, spesielt arylsulfonsyrene, hudirritasjon, men det er funnet at dette for det meste kan unngås ved å innblande mindre mengder av et polyvinylpyrrolidon- eller et nonylfenol-etylenoksyd-produkt i preparatene ifølge oppfinnelsen. At high application concentrations, some of the preparations according to the invention, especially the arylsulfonic acids, exhibit skin irritation, but it has been found that this can mostly be avoided by mixing smaller amounts of a polyvinylpyrrolidone or a nonylphenol ethylene oxide product into the preparations according to the invention.
Misfarging av substraten kan forekomme men dette kan ofte unngås ved å bringe det behandlede substrat, som f.eks. ved, i kontakt med en vannløsning av monoammoniumfosfat. Mørkfarging kan også opptre som følge av en kjemisk reaksjon, som f .eks. med jern, og korrosjonsinhibitorer kan med fordel innblandes i preparatene ifølge oppfinnelsen. Discoloration of the substrate can occur, but this can often be avoided by bringing the treated substrate, such as by, in contact with an aqueous solution of monoammonium phosphate. Darkening can also occur as a result of a chemical reaction, such as e.g. with iron, and corrosion inhibitors can advantageously be mixed into the preparations according to the invention.
Claims (8)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62574175A | 1975-10-24 | 1975-10-24 |
Publications (3)
Publication Number | Publication Date |
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NO763453L NO763453L (en) | 1977-04-26 |
NO156672B true NO156672B (en) | 1987-07-27 |
NO156672C NO156672C (en) | 1987-11-04 |
Family
ID=24507378
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO763453A NO156672C (en) | 1975-10-24 | 1976-10-08 | PREPARATION WITH ANTIMICROBIAL AND ANY POSSIBLE INSECTICID EFFECT AND USE OF SUCH A PREPARATION AS A TREE AND ANTI-PROTECTIVE AGENT. |
Country Status (23)
Country | Link |
---|---|
JP (1) | JPS5257327A (en) |
AR (1) | AR223953A1 (en) |
AT (1) | AT380427B (en) |
AU (1) | AU512550B2 (en) |
BE (1) | BE847405A (en) |
BR (1) | BR7607040A (en) |
CA (1) | CA1115205A (en) |
CH (1) | CH621040A5 (en) |
DE (1) | DE2647952A1 (en) |
ES (1) | ES452679A1 (en) |
FR (1) | FR2328481A1 (en) |
GB (1) | GB1571814A (en) |
GR (1) | GR65588B (en) |
IN (1) | IN145040B (en) |
IT (1) | IT1202352B (en) |
NL (1) | NL7611750A (en) |
NO (1) | NO156672C (en) |
OA (1) | OA05460A (en) |
PH (1) | PH16580A (en) |
PT (1) | PT65735B (en) |
SE (1) | SE439415B (en) |
SU (1) | SU917681A3 (en) |
ZA (1) | ZA766268B (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4185120A (en) * | 1978-10-02 | 1980-01-22 | Abbott Laboratories | Topical treatment of fungal or yeast infections using p-tolyl diiodomethyl sulfone |
GB2119653A (en) * | 1982-05-17 | 1983-11-23 | Ici Plc | Pesticidal compositions |
JPS6023082B2 (en) * | 1982-11-12 | 1985-06-05 | 昭和電線電纜株式会社 | termiticide |
BR8503466A (en) * | 1984-08-02 | 1986-04-15 | Rohm & Haas | METHOD FOR KILLING AND REPELLING WOOD DESTROYING INSECTS |
HU196554B (en) * | 1986-04-18 | 1988-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for production of medical compounds with fungicidal effect |
NZ221631A (en) * | 1986-09-05 | 1990-01-29 | Abbott Lab | Insecticidal compositions containing diiodomethylsulphone derivatives |
JPH0298157A (en) * | 1988-10-04 | 1990-04-10 | Matsushita Electron Corp | Semiconductor element pickup device |
JPH0327303A (en) * | 1989-06-23 | 1991-02-05 | Hokko Chem Ind Co Ltd | Preservative and fungicide for industry |
DE4241079C2 (en) * | 1992-12-05 | 1996-04-04 | Bode Chemie Gmbh & Co | Surface disinfectant, especially for plastic surfaces |
US7585980B2 (en) * | 2006-05-25 | 2009-09-08 | Troy Corporation | Immobilized 1,2-benzisothiazolin-3-one |
RU2600949C1 (en) * | 2015-09-07 | 2016-10-27 | Автономная некоммерческая организация высшего образования "Белгородский университет кооперации, экономики и права" | Fungicidal additive for mineral construction compositions |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2614918A (en) * | 1945-10-25 | 1952-10-21 | Monsanto Chemicals | Method of setting fruit and composition therefor |
US2898267A (en) * | 1955-09-07 | 1959-08-04 | Witco Chemical Corp | Emulsifiable toxicant compositions and emulsifying agents therefor |
US3141821A (en) * | 1959-03-17 | 1964-07-21 | Lehn & Fink Products Corp | Synergistic combination of alkyl sulfonates, alkylaryl sulfonates and topical antibacterial agents for local antisepsis |
US3485919A (en) * | 1963-09-05 | 1969-12-23 | Procter & Gamble | Antibacterial composition |
CH501364A (en) * | 1967-04-11 | 1971-01-15 | Du Pont | 2-Benzimidazolecarbamic acid alkyl esters - fungicidal compsns. |
DE1792687A1 (en) * | 1967-05-03 | 1971-11-25 | Du Pont | Fungicidal agent |
FR2015139A1 (en) * | 1968-08-06 | 1970-04-24 | Sanyo Chemical Cy Ltd | |
US3914308A (en) * | 1969-11-20 | 1975-10-21 | Texaco Inc | Solubilizing process |
US3681348A (en) * | 1969-11-20 | 1972-08-01 | Texaco Inc | Oil-solubilizing nitrogen-containing pesticidal compounds |
DE2053356B2 (en) * | 1970-10-30 | 1978-09-21 | Basf Ag, 6700 Ludwigshafen | Two-component emulsifier system for the formulation of pesticides |
-
1976
- 1976-10-08 NO NO763453A patent/NO156672C/en unknown
- 1976-10-15 IN IN1888/CAL/76A patent/IN145040B/en unknown
- 1976-10-18 GR GR51964A patent/GR65588B/en unknown
- 1976-10-18 BE BE171606A patent/BE847405A/en not_active IP Right Cessation
- 1976-10-20 PH PH19021A patent/PH16580A/en unknown
- 1976-10-20 PT PT65735A patent/PT65735B/en unknown
- 1976-10-20 FR FR7631501A patent/FR2328481A1/en active Granted
- 1976-10-21 ZA ZA766268A patent/ZA766268B/en unknown
- 1976-10-21 SE SE7611699A patent/SE439415B/en not_active IP Right Cessation
- 1976-10-21 BR BR7607040A patent/BR7607040A/en unknown
- 1976-10-21 CH CH1334976A patent/CH621040A5/en not_active IP Right Cessation
- 1976-10-22 SU SU762415364A patent/SU917681A3/en active
- 1976-10-22 AT AT0788376A patent/AT380427B/en not_active IP Right Cessation
- 1976-10-22 NL NL7611750A patent/NL7611750A/en unknown
- 1976-10-22 AR AR265191A patent/AR223953A1/en active
- 1976-10-22 OA OA55961A patent/OA05460A/en unknown
- 1976-10-22 DE DE19762647952 patent/DE2647952A1/en active Granted
- 1976-10-23 ES ES452679A patent/ES452679A1/en not_active Expired
- 1976-10-23 GB GB44072/76A patent/GB1571814A/en not_active Expired
- 1976-10-23 JP JP51126813A patent/JPS5257327A/en active Granted
- 1976-10-25 CA CA264,121A patent/CA1115205A/en not_active Expired
- 1976-10-25 AU AU18938/76A patent/AU512550B2/en not_active Expired
- 1976-10-25 IT IT85602/76A patent/IT1202352B/en active
Also Published As
Publication number | Publication date |
---|---|
SE439415B (en) | 1985-06-17 |
AU512550B2 (en) | 1980-10-16 |
ZA766268B (en) | 1977-09-28 |
GR65588B (en) | 1980-10-14 |
IN145040B (en) | 1978-08-12 |
NL7611750A (en) | 1977-04-26 |
BR7607040A (en) | 1977-09-06 |
JPS6144841B2 (en) | 1986-10-04 |
CH621040A5 (en) | 1981-01-15 |
BE847405A (en) | 1977-04-18 |
ATA788376A (en) | 1985-10-15 |
FR2328481B1 (en) | 1982-10-29 |
CA1115205A (en) | 1981-12-29 |
JPS5257327A (en) | 1977-05-11 |
GB1571814A (en) | 1980-07-23 |
SE7611699L (en) | 1977-04-25 |
PT65735A (en) | 1976-11-01 |
FR2328481A1 (en) | 1977-05-20 |
AU1893876A (en) | 1978-05-04 |
DE2647952A1 (en) | 1977-05-05 |
ES452679A1 (en) | 1978-04-16 |
NO763453L (en) | 1977-04-26 |
IT1202352B (en) | 1989-02-09 |
OA05460A (en) | 1981-03-31 |
AT380427B (en) | 1986-05-26 |
PT65735B (en) | 1978-04-18 |
DE2647952C2 (en) | 1991-12-19 |
SU917681A3 (en) | 1982-03-30 |
PH16580A (en) | 1983-11-22 |
AR223953A1 (en) | 1981-10-15 |
NO156672C (en) | 1987-11-04 |
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