NO874171L - BACTERICIDE MIXTURES CONTAINING NITROIMIDAZOLE SALTS. - Google Patents
BACTERICIDE MIXTURES CONTAINING NITROIMIDAZOLE SALTS. Download PDFInfo
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- NO874171L NO874171L NO874171A NO874171A NO874171L NO 874171 L NO874171 L NO 874171L NO 874171 A NO874171 A NO 874171A NO 874171 A NO874171 A NO 874171A NO 874171 L NO874171 L NO 874171L
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- Prior art keywords
- salt
- nitroimidazole
- srb
- preventing
- sulfate
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- 239000000203 mixture Substances 0.000 title claims abstract description 26
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 20
- 150000004957 nitroimidazoles Chemical class 0.000 title claims description 26
- 239000003899 bactericide agent Substances 0.000 title description 9
- 241000894006 Bacteria Species 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000012530 fluid Substances 0.000 claims description 19
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 238000005188 flotation Methods 0.000 claims description 7
- 238000012360 testing method Methods 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000003860 storage Methods 0.000 claims description 5
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000007797 corrosion Effects 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000005540 biological transmission Effects 0.000 claims description 2
- 238000005520 cutting process Methods 0.000 claims description 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethanedisulfonate group Chemical group C(CS(=O)(=O)[O-])S(=O)(=O)[O-] AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 claims description 2
- 230000002706 hydrostatic effect Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- -1 organic acid salt Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 11
- 239000007864 aqueous solution Substances 0.000 claims 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical group CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 6
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 6
- UBQLFSIVOXQYEL-UHFFFAOYSA-N 1,2-dimethyl-5-nitroimidazole;hydron;chloride Chemical compound Cl.CC1=NC=C([N+]([O-])=O)N1C UBQLFSIVOXQYEL-UHFFFAOYSA-N 0.000 description 5
- 229960000946 dimetridazole Drugs 0.000 description 5
- 229960000282 metronidazole Drugs 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- KPQZUUQMTUIKBP-UHFFFAOYSA-N 1-(2-methyl-5-nitro-1-imidazolyl)-2-propanol Chemical compound CC(O)CN1C(C)=NC=C1[N+]([O-])=O KPQZUUQMTUIKBP-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NTAFJUSDNOSFFY-UHFFFAOYSA-N Ipronidazole Chemical compound CC(C)C1=NC=C([N+]([O-])=O)N1C NTAFJUSDNOSFFY-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- 238000009713 electroplating Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229950000107 ipronidazole Drugs 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229960004076 secnidazole Drugs 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000019086 sulfide ion homeostasis Effects 0.000 description 2
- 150000003892 tartrate salts Chemical class 0.000 description 2
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 2
- LAFKJOOLIQEVKN-UHFFFAOYSA-N 2-(3-methyl-5-nitro-2H-imidazol-1-yl)ethanol Chemical compound OCCN1CN(C=C1[N+](=O)[O-])C LAFKJOOLIQEVKN-UHFFFAOYSA-N 0.000 description 1
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010001981 Amoebic infections Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000010362 Protozoan Infections Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical class OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000012994 industrial processing Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Baktericide blandinger som inneholder nitroinidazolsalter.Disse brukes til a forhindre vekstgraden av sulfat-reduserende bakterier.Bactericidal mixtures containing nitroinidazole salts. These are used to prevent the growth rate of sulfate-reducing bacteria.
Description
Denne oppfinnelsen vedrører baktericide blandinger omfattende nitroimidazol-salter og industrielle blandinger inneholdende slike baktericide blandinger og anvendelsen av baktericide blandinger for å inhibere veksten av mikro-organismer i industrielle vandige væsker som inneholder organiske materialer. Nærmere bestemt vedrører oppfinnelsen anvendelse av salter av mikro-organismer alene eller i forbindelse med andre kjente baktericider for å inhibere bakterievekst i industrielle vandige væsker som inneholder organiske materialer. This invention relates to bactericidal compositions comprising nitroimidazole salts and industrial compositions containing such bactericidal compositions and the use of bactericidal compositions to inhibit the growth of micro-organisms in industrial aqueous liquids containing organic materials. More specifically, the invention relates to the use of salts of micro-organisms alone or in conjunction with other known bactericides to inhibit bacterial growth in industrial aqueous liquids containing organic materials.
Nærvær av sulfat-reduserende bakterier (SRB) i flytende organiske materialer og vandige væsker som inneholder organiske materialer, er et alvorlig industrielt problem, da slike bakterier metaboliserer sulfater under frigjøring av hydrogensulfid og dermed fører til rotten lukt og korrosjon pga. det frigjorte hydrogensulfid. Nærværet av SRB i hydrokarbonstrømmer, vegetabilske oljer, brenselsoljer, smøreoljer, mineralolje-baserte hydrauliske fluider, olje/vann- og vann/olje-emulsjoner, slik som brukes i metallbehandlingsfluider og hydrauliske fluider og i vandige væsker som inneholder slike materialer, er eksempler på materialer som angripes av SRB. Eksempler på industrielle væsker som påvirkes av nærværet av SRB er papir-sulfittmasse-behandlingsvæsker, industrielt prosessvann, elektro-pletteringsløsninger, oljebrønn-injeksjonsvann så som vannfIotasjonsvæsker, polymerfIotasjonsvæsker, frakturerings-fluider og lignende, lagringstanker som brukes for å lagre emulsjoner av vann og olje og lignende. The presence of sulfate-reducing bacteria (SRB) in liquid organic materials and aqueous liquids containing organic materials is a serious industrial problem, as such bacteria metabolize sulfates to release hydrogen sulfide and thus lead to putrid odors and corrosion due to the liberated hydrogen sulphide. The presence of SRB in hydrocarbon streams, vegetable oils, fuel oils, lubricating oils, mineral oil-based hydraulic fluids, oil/water and water/oil emulsions, such as those used in metalworking fluids and hydraulic fluids and in aqueous fluids containing such materials, are examples of materials attacked by SRB. Examples of industrial fluids affected by the presence of SRB are paper-sulfite pulp treatment fluids, industrial process water, electroplating solutions, oil well injection water such as water flotation fluids, polymer flotation fluids, fracturing fluids and the like, storage tanks used to store emulsions of water and oil and such.
Da SRB gir alvorlige lukt- og korrosjons-problemer på praktisk talt alle felter av industriell behandling, søker industrien stadig etter mer effektive baktericide materialer for å forhindre veksten av SRB. Since SRB present serious odor and corrosion problems in virtually all fields of industrial processing, the industry is constantly searching for more effective bactericidal materials to prevent the growth of SRB.
Forskjellige materialer er derfor blitt brukt til å inhibere SRB i industrivæsker. Slike kjente baktericider innbefatter nitroimidazoler, aldehyder, isotiazoloner, fenoler, tungmetall-forbindelser akrolein og annet. Alle disse kjente baktericide materialene er effektive mot SRB i varierende grad, men bruken av dem alle medfører visse problemer. Således gir noen av materialene problemer med giftighet, noen av materialene er meget dyre i bruk, andre medfører løselighetsproblemer i vandige væsker, andre er ikke forenelige medønskede eller nødvendige kjemiske additiver, og andre forblir som rester i vann i tilstrekkelig høye konsentrasjoner til å gjøre vannet giftig. Visse åv materialene er temmelig korroderende på metaller. Different materials have therefore been used to inhibit SRB in industrial fluids. Such known bactericides include nitroimidazoles, aldehydes, isothiazolones, phenols, heavy metal compounds acrolein and others. All of these known bactericidal materials are effective against SRB to varying degrees, but the use of all of them entails certain problems. Thus, some of the materials cause problems with toxicity, some of the materials are very expensive to use, others cause solubility problems in aqueous liquids, others are not compatible with desired or necessary chemical additives, and others remain as residues in water in sufficiently high concentrations to make the water poisonous. Certain of the materials are quite corrosive to metals.
Med hensyn til foreliggende oppfinnelse beskriver U.S. patent 2.94.061 anvendelsen av salter av 2-metyl-5-nitroimidazol-1-etanol(metranidazol) i behandlingen av amøbe- og protozo-infeksjoner. Videre beskriver U.S.patent 4.395.341 anvendelse av metranidazol som et baktericid i fIotasjonsvann som injiseres i oljeholdige formasjoner. Ytterligere beskriver Britisk patent-søknad 2103928 anvendelsen av forskjellige nitroimidazoler for å inhibere ødeleggelse av flytende organiske materialer. With respect to the present invention, U.S. Pat. patent 2.94.061 the use of salts of 2-methyl-5-nitroimidazole-1-ethanol (metranidazole) in the treatment of amoebic and protozoan infections. Furthermore, U.S. Patent 4,395,341 describes the use of metronidazole as a bactericide in flotation water injected into oily formations. Furthermore, British Patent Application 2103928 describes the use of various nitroimidazoles to inhibit the destruction of liquid organic materials.
Selvom nitroimidazolene som tidligere er beskrevet, er funnet å være effektive mot visse bakterier, f.eks. SRB, har nitroimidazolene den ulempe at de bare er lite oppløselige i Although the nitroimidazoles previously described have been found to be effective against certain bacteria, e.g. SRB, the nitroimidazoles have the disadvantage that they are only slightly soluble in
vann. Åpenbart er et baktericid som skal brukes i vandige væsker lettere å bruke, er mindre dyrt og er mer effektivt hvis water. Obviously, a bactericide to be used in aqueous liquids is easier to use, is less expensive and is more effective if
det er lett å løse i den vandige væsken.it is easy to dissolve in the aqueous liquid.
Følgelig er det et mål for foreliggende oppfinnelse å Accordingly, it is an object of the present invention to
tilveiebringe baktericide nitroimidazol-blandinger som er fritt oppløselig i vandige væsker og som er meget effektive ved inhibering av veksten av SRB. provide bactericidal nitroimidazole compositions which are freely soluble in aqueous liquids and which are highly effective in inhibiting the growth of SRB.
Ifølge foreliggende oppfinnelse har man funnet at syre- og ammonium-addisjonssalter av nitroimidazoler og kvarternære derivater derav er meget effektive baktericider ved inhibering av SRB og er mindre dyre og lettere å bruke pga. deres høye vannløselighet enn nitroimidazolene i seg selv. Nitroimidazol-saltene som brukes i foreliggende oppfinnelse kan brukes alene According to the present invention, it has been found that acid and ammonium addition salts of nitroimidazoles and quaternary derivatives thereof are very effective bactericides when inhibiting SRB and are less expensive and easier to use because their high water solubility than the nitroimidazoles themselves. The nitroimidazole salts used in the present invention can be used alone
eller i forbindelse med andre anaerobe og aerobe baktericider som er kjent på området. or in connection with other anaerobic and aerobic bactericides known in the field.
Baktericidene som brukes i foreliggende oppfinnelse er salter av 1-(2-hydroksyetyl)-3-metyl-5-nitroimidazol(metranidazol) , 1,2-dimetyl-5-nitroimidazol (dimetridazol), l-(2-hydroksypropyl)-2-metyl-5-nitroimidazol (seknidazol) og 1-metyl-2-isopropyl-3-nitroimidazol(ipronidazol). The bactericides used in the present invention are salts of 1-(2-hydroxyethyl)-3-methyl-5-nitroimidazole (metranidazole), 1,2-dimethyl-5-nitroimidazole (dimetridazole), l-(2-hydroxypropyl)-2 -methyl-5-nitroimidazole (secnidazole) and 1-methyl-2-isopropyl-3-nitroimidazole (ipronidazole).
Saltene av de ovenfornevnte nitroimidazoler innbefatter syreaddisjonssaltene så som hydrohalogenidene, f.eks. hydro klorid, hydrobromid og hydrojodid, fosfater, nitrater, sulfater, acetater, propionater, maleater, fumarater, citrater, tartrater, adipater, metansulfonater, etandisulfonater og lignende og innbefatter også ammoniumsaltene og kvarternære ammoniumforbin-delser. The salts of the above-mentioned nitroimidazoles include the acid addition salts such as the hydrohalides, e.g. hydrochloride, hydrobromide and hydroiodide, phosphates, nitrates, sulphates, acetates, propionates, maleates, fumarates, citrates, tartrates, adipates, methanesulphonates, ethanedisulphonates and the like and also includes the ammonium salts and quaternary ammonium compounds.
Nitroimidazol-forbindelsene som brukes i foreliggende oppfinnelse, er kjente forbindelser, og deres fremstillings-metode er velkjent for en fagmann. Likeledes er syreaddisjonssaltene, ammoniumssaltene og kvarternære derivater lette å fremstille for en fagmann. The nitroimidazole compounds used in the present invention are known compounds, and their preparation method is well known to a person skilled in the art. Likewise, the acid addition salts, ammonium salts and quaternary derivatives are easy to prepare for a person skilled in the art.
Nitroimidazol-saltene i foreliggende oppfinnelse brukes i konsentrasjoner fra ca. 0,1 ppm til ca. 25 ppm aktiv bestanddel, fortrinnsvis fra ca. 0,2 ppm til ca. 1 ppm aktiv bestanddel. The nitroimidazole salts in the present invention are used in concentrations from approx. 0.1 ppm to approx. 25 ppm active ingredient, preferably from approx. 0.2 ppm to approx. 1 ppm active ingredient.
De følgende eksempler illustrerer spesifikke, ikke-begrensende utførelsesformer av oppfinnelsen innbefattet den beste utførelsesform av oppfinnelsen. The following examples illustrate specific, non-limiting embodiments of the invention including the best embodiment of the invention.
I de følgende eksempler er den bakteristatiske prøven forIn the following examples, the bacteriostatic test is for
å bestemme inhibering av sulfat-reduserende bakterie som følger: 1. A sette sammen to rekker som hver inneholder seks sulfat API medium flasker (9,0 ml hver). to determine inhibition of sulfate-reducing bacteria as follows: 1. Assemble two rows each containing six sulfate API medium bottles (9.0 ml each).
2. A overføre 0,1 - 0,5 ml forsøksforbindelses-løsning2. Transfer 0.1 - 0.5 ml test compound solution
fra en tilsvarende stamløsning slik at man får de følgende slutt-konsentrasjoner i sulfat API medium flaskene: 0, 10, 20, 40, 80 og 160 ppm (rist flaskene for å sikre jevn fordeling av prøveløsningen). 3. A innokulere hver prøveflaske innbefattet kontroll med 0,5 ml av en 24-timers kultur av "felt-stamme" sulfat-reduserende bakterier. 4. A inkubere i det angitte antall dager ved 35°C. Resultatene registreres etter det angitte tidsrom. Mørkning viser vekst av sulfatreduserende bakterier. Det bakteriostatiske nivå er den laveste konsentrasjon som ikke viser noen mørkning. from a corresponding stock solution so that the following final concentrations are obtained in the sulphate API medium bottles: 0, 10, 20, 40, 80 and 160 ppm (shake the bottles to ensure even distribution of the sample solution). 3. Inoculate each sample bottle including the control with 0.5 ml of a 24-hour culture of "field-strain" sulfate-reducing bacteria. 4. Incubate for the indicated number of days at 35°C. The results are recorded after the specified time period. Darkening indicates the growth of sulfate-reducing bacteria. The bacteriostatic level is the lowest concentration that shows no darkening.
Eksempel 1Example 1
I dette eksempel påvises effektiviteten til dimetridazol-hydroklorid ved inhibering av veksten av SRB og anaerobe bakterier og sammenlignes mot dimetridazol og metranidazol. Resultatene er vist i tabell I som angir data man får fra et laboratorieforsøk som viser inhibering av hydrogensulfid-produksjon og baktericid-aktivitet mot sulfatreduserende bakterier. Forsøket ble satt opp ved bruk av et modifisert sulfat API medium som forsøksmedium. Forsøksmediet ble spylt med argon for å fjerne oppløst oksygen og fordelt i 100 ml argon-spylte serumglass. De ble deretter sterilisert. Forskjellige konsentrasjoner av metranidazol, dimetridazol og dimetridazol-hydroklorid ble fremstilt fra 1 % -løsninger. Hvert glass ble innokulert med 2 ml av en 1-10 fortynning av en 24 timer gammel kultur av "felt-stamme" sulfatreduserende bakterier. Etter 1, 2 og 7 dagers eksponeringer ble mengdene av overlevende SRB og konsentrasjoner av hydrogensulfid målt. In this example, the effectiveness of dimetridazole hydrochloride in inhibiting the growth of SRB and anaerobic bacteria is demonstrated and compared against dimetridazole and metronidazole. The results are shown in table I, which indicates data obtained from a laboratory experiment showing inhibition of hydrogen sulfide production and bactericidal activity against sulfate-reducing bacteria. The experiment was set up using a modified sulphate API medium as the experimental medium. The test medium was flushed with argon to remove dissolved oxygen and dispensed into 100 ml argon-flushed serum vials. They were then sterilized. Different concentrations of metronidazole, dimetridazole and dimetridazole hydrochloride were prepared from 1% solutions. Each glass was inoculated with 2 ml of a 1-10 dilution of a 24-hour-old culture of "field-strain" sulfate-reducing bacteria. After 1, 2 and 7 days of exposure, the amounts of surviving SRB and concentrations of hydrogen sulfide were measured.
Disse data er oppstilt i tabell I. These data are listed in Table I.
Dataene i tabell I illustrerer at dimetridazolhydroklorid er en sterk inhibitor for hydrogensulfid-produksjon av SRB. Det var også baktericid og drepte fullstendig SRB ved 0,6 ppm aktiv bestanddel, selv etter gjentatt infeksjon med bakterier. Til sammenligning av 1,6 ppm aktivt metranidazol nødvendig for å drepe SRB fullstendig etter 7 dagers eksponering. The data in Table I illustrate that dimetridazole hydrochloride is a strong inhibitor of hydrogen sulfide production by SRB. It was also bactericidal and completely killed SRB at 0.6 ppm active ingredient, even after repeated infection with bacteria. In comparison, 1.6 ppm active metronidazole required to completely kill SRB after 7 days of exposure.
Eksempel 2Example 2
Dette eksempel presenterer resultatene av et felt-av-livnings-forsøk foretatt ved et teknisk vann-annlegg. Det produserte vann ved anlegget var et moderat saltvann og inneholdt ca. 40 ppm hydrogensulfid. Det produserte vann ble fordelt i 50 ml argon-spylte serumglass. Forskjellige konsentrasjoner av dimetridazol og dimetridazol-hydroklorid ble laget. Etter 24 timers eksponering ble nivåer av SRB, anaerobe bakterier og totale bakterier ved ATP målt. Resultatene er oppført tabellarisk i tabell 2. This example presents the results of a field survival test carried out at a technical water installation. The water produced at the plant was moderately saline and contained approx. 40 ppm hydrogen sulphide. The produced water was dispensed into 50 ml argon-flushed serum vials. Different concentrations of dimetridazole and dimetridazole hydrochloride were prepared. After 24 hours of exposure, levels of SRB, anaerobic bacteria and total bacteria at ATP were measured. The results are tabulated in table 2.
Resultatene som er illustrert i tabell 2 viser at mengder opp til 24 ppm aktivt dimetridazol ikke hadde noen virkning på The results illustrated in Table 2 show that amounts up to 24 ppm of active dimetridazole had no effect on
bakterier som er tilstede i det produserte vann. Dimetridazol-hydrokloridet reduserte SRB mengder med 90 % ved 24 ppm aktiv konsentrasjon. bacteria present in the produced water. Dimetridazole hydrochloride reduced SRB amounts by 90% at 24 ppm active concentration.
Det forutsettes at saltene av metranidazol, ipronidazol og secnidazol ville være lignende effektive, og at i tillegg til hydroklorid-saltet som er illustrert i de ovenfornevnte eksempler, ville hydrobromidet, hydrojodidet og fosfatene, nitratene, sulfatene, acetatene, propionatene, maleatene, fumaratene, citratene, adipatene, tartratene, metansulfonatene, etandisulfonatene og ammoniumsaltene være lignende effektive. Videre forutsettes det at de kvarternære ammoniumsalter også kunne brukes med lignende resultater. It is anticipated that the salts of metronidazole, ipronidazole, and secnidazole would be similarly effective, and that in addition to the hydrochloride salt illustrated in the above examples, the hydrobromide, hydroiodide, and phosphates, nitrates, sulfates, acetates, propionates, maleates, fumarates, the citrates, adipates, tartrates, methanesulfonates, ethanedisulfonates and ammonium salts being similarly effective. Furthermore, it is assumed that the quaternary ammonium salts could also be used with similar results.
Nitroimidazolsaltene kan brukes i forbindelse med andre baktericider innbefattende aldehyder, forbindelser som frigjør aldehyder, fenoler, f.eks. p-klor-m-kresol og fenol, tung-metaller, isotiazoloner, blandinger av halogenerte og ikke-halogenerte isotiazoloner og blandinger derav. Baktericide blandinger som inneholder nitroimidazolsaltene i foreliggende oppfinnelse kan brukes i oljefelt- og industrielle-hydrokarbon-væsker og i blandinger, dispersjoner eller emulsjoner av hydrokarbon og vandige væsker, f.eks. nedhulls-injeksjonsvann så som fIotasjons-vann, fIotasjonspolymerer og frakturering-svæsker. 01je-i-vann og vann-i-olje emulsjoner, gassoverførings-ledninger og lagrings-områder, i hydrostatisk utprøving av utstyr så som tanker, kjeler og rørledninger, i kappings- og metall-behandlingsvæsker, i oljelagringstanker og industrielle prosessvann, i papir-sulfitt-masse-behandlingsfluider, i elektropletteringsløsninger og i rør, filtre og annet utstyr som skal brukes for å produsere, transportere og lagre oljefelt-og industrielle prosessvanns-væsker. The nitroimidazole salts can be used in conjunction with other bactericides including aldehydes, compounds which release aldehydes, phenols, e.g. p-chloro-m-cresol and phenol, heavy metals, isothiazolones, mixtures of halogenated and non-halogenated isothiazolones and mixtures thereof. Bactericidal compositions containing the nitroimidazole salts of the present invention can be used in oilfield and industrial hydrocarbon fluids and in mixtures, dispersions or emulsions of hydrocarbon and aqueous fluids, e.g. downhole injection water such as flotation water, flotation polymers and fracturing fluids. 01je-in-water and water-in-oil emulsions, gas transmission lines and storage areas, in hydrostatic testing of equipment such as tanks, boilers and pipelines, in cutting and metal treatment fluids, in oil storage tanks and industrial process water, in paper -sulphite pulp treatment fluids, in electroplating solutions and in pipes, filters and other equipment to be used to produce, transport and store oilfield and industrial process water fluids.
Skjønt de illustrerende utførelsesformer av oppfinnelsen er blitt beskrevet spesielt, vil det være klart at forskjellige andre modifikasjoner vil være åpenbare og lett kan foretas av en fagmann på området uten at man går utenfor oppfinnelses-tanken og omfanget derav. Følgelig er det ikke ment at omfanget av de medfølgende krav skal være begrenset til eksemplene og beskrivelsen som her er gitt, men tvert i mot skal kravene anses som å omfatte alle trekk av patenterbar nyhet som ligger i oppfinnelsen, innbefattet alle trekk som ville behandles som ekvivalenter derav for en fagmann på området som oppfinnelsen angår. Although the illustrative embodiments of the invention have been specifically described, it will be clear that various other modifications will be obvious and can be easily made by one skilled in the art without departing from the spirit and scope of the invention. Consequently, it is not intended that the scope of the accompanying claims shall be limited to the examples and description given here, but on the contrary, the claims shall be considered to include all features of patentable novelty contained in the invention, including all features that would be treated as equivalents thereof for a person skilled in the art to which the invention relates.
Claims (25)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91676186A | 1986-10-05 | 1986-10-05 |
Publications (2)
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| NO874171D0 NO874171D0 (en) | 1987-10-05 |
| NO874171L true NO874171L (en) | 1988-04-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO874171A NO874171L (en) | 1986-10-06 | 1987-10-05 | BACTERICIDE MIXTURES CONTAINING NITROIMIDAZOLE SALTS. |
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| GB (1) | GB2195536A (en) |
| NO (1) | NO874171L (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB837838A (en) * | 1957-09-14 | 1960-06-15 | Rhone Poulenc Sa | New imidazole derivatives and processes for their preparation |
| FR1427627A (en) * | 1963-10-10 | 1966-02-11 | Rhone Poulenc Sa | New imidazole derivatives and their preparation |
| US3976778A (en) * | 1973-08-13 | 1976-08-24 | Ciba-Geigy Corporation | Imidazoles and processes for their production |
| US4395341A (en) * | 1977-07-21 | 1983-07-26 | G. D. Searle & Co. | Use of metronidazole in oil recovery |
| FR2517969B1 (en) * | 1981-08-21 | 1986-07-18 | May & Baker Ltd | METHOD FOR CONTROLLING THE ALTERATION OF TECHNICAL LIQUIDS USING NITROIMIDAZOLE DERIVATIVES |
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| Publication number | Publication date |
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| NO874171D0 (en) | 1987-10-05 |
| GB2195536A (en) | 1988-04-13 |
| GB8716647D0 (en) | 1987-08-19 |
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