AU2002302387A1 - Antimicrobial compositions - Google Patents
Antimicrobial compositionsInfo
- Publication number
- AU2002302387A1 AU2002302387A1 AU2002302387A AU2002302387A AU2002302387A1 AU 2002302387 A1 AU2002302387 A1 AU 2002302387A1 AU 2002302387 A AU2002302387 A AU 2002302387A AU 2002302387 A AU2002302387 A AU 2002302387A AU 2002302387 A1 AU2002302387 A1 AU 2002302387A1
- Authority
- AU
- Australia
- Prior art keywords
- oxide
- oxathiazine
- benzo
- dihydro
- thiene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 64
- 230000000845 anti-microbial effect Effects 0.000 title claims description 56
- -1 3-iodo-2-propynyl Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
- 239000004599 antimicrobial Substances 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 claims description 12
- 241000195493 Cryptophyta Species 0.000 claims description 12
- 241000233866 Fungi Species 0.000 claims description 12
- HDHLIWCXDDZUFH-UHFFFAOYSA-N irgarol 1051 Chemical compound CC(C)(C)NC1=NC(SC)=NC(NC2CC2)=N1 HDHLIWCXDDZUFH-UHFFFAOYSA-N 0.000 claims description 12
- 241000894006 Bacteria Species 0.000 claims description 11
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims description 11
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims description 10
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 8
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 claims description 8
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 claims description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 5
- 230000002195 synergetic effect Effects 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- 125000005610 enamide group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 claims 1
- 239000001963 growth medium Substances 0.000 description 18
- 238000011081 inoculation Methods 0.000 description 11
- 239000003139 biocide Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 230000012010 growth Effects 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910001385 heavy metal Inorganic materials 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000005747 Chlorothalonil Substances 0.000 description 5
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 5
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 5
- 230000002411 adverse Effects 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 238000009631 Broth culture Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000001965 potato dextrose agar Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical class O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NRAYWXLNSHEHQO-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-5,6-dihydro-1,4,2-oxathiazine 4-oxide Chemical compound O=S1CCON=C1C1=CC2=CC=CC=C2S1 NRAYWXLNSHEHQO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 241000228212 Aspergillus Species 0.000 description 1
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000222290 Cladosporium Species 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- FARBQUXLIQOIDY-UHFFFAOYSA-M Dioctyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(C)CCCCCCCC FARBQUXLIQOIDY-UHFFFAOYSA-M 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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Description
ANTIMICROBIAL COMPOSITIONS
This invention concerns antimicrobial compositions that are useful for industrial applications. More specifically, it concerns antimicrobial compositions that, by combining 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and one or more of l-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene, l-chloro-4-[[(3- iodo-2-propynyl)oxy]methoxy] benzene, Zinc 2-pyridine thiol-1 -oxide, Copper 2- pyridine thiol-1 -oxide, 2-pyridine thiol-1 -oxide sodium salt, 2,2-dithio-bis(pyridine-l- oxide), 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine, 3-iodo-2- propynyl butylcarbamate (IPBC), 2-(n-octyl)-3(2H)-isothiazolone (OIT), 4,5-dichloro- 2-(n-octyl)-3(2H)-isothiazolone (DCOIT), 2,4,5,6-tetrachloro- 1 ,3-benzenedicarbonitrile (chlorothalonil), 1 , l-dichloro-N-[(dimethylamino)sulfonyl]- 1-fluoro-N-phenyl- methanesulfenamide (dichlofluanid), or l,l-dichloro-N-[(dimethylamino)sulfonyl]-l- fluoro-N-(4~methylphenyl)-memanesulfenamide (tolylfluanid) have the synergistic effect of these compounds.
Inorganic or organic compounds that contain mainly mercury, tin, copper, and other heavy metals (hereafter called "heavy-metal compounds") have been widely used as antimicrobial agents for industrial products and industrial raw materials. But the high toxicity of these heavy-metal compounds poses the danger of adversely affecting the human body. In addition, heavy-metal compounds are not suitable for use as antimicrobial agents because of the fear that heavy-metal compounds may lead to environmental destruction.
The many non-metallic antimicrobial agents that have been developed to solve such problems of heavy metal compounds (for example, organic iodine compounds, nitrile compounds, isothiazolone compounds, benzimidazole compounds, pyrithione compounds) have selectivity in their antimicrobial spectrum. Thus even if these non- metallic antimicrobial agents are applied to industrial products or industrial raw materials, in particular organic materials (for example, fibre, paint, adhesives, etc.), micro-organisms on which these antimicrobial agents have little or no effect will grow and propagate, thus allowing the occurrence of contamination of industrial products, etc. or a change in the quality (for example, degradation) of industrial raw materials. Therefore satisfactory antimicrobial effect cannot be obtained by conventional antimicrobial compositions.
Thus attempts have been made to expand the antimicrobial spectrum and increase the antimicrobial effect by combining two or more antimicrobial agents. But usually either
the effect of only one of the antimicrobial agents appears, or only an additive effect is obtained.
The purpose of this invention, which is intended to solve the above problems, is to provide antimicrobial compositions that are highly safe, are very effective, and have a wide antimicrobial spectrum.
As a result of diligent study to solve the above problems, the inventors of this invention found that an unexpected synergistic effect is obtained by combining with 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide one or more of the following compounds (a)-(m):
(a) l-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene
(b) l-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene
(c) Zinc 2-pyridine thiol-1 -oxide (d) Copper 2-pyridine thiol-1 -oxide
(e) 2-pyridine thiol-1 -oxide sodium salt
(f) 2,2-dithio-bis(pyridine- 1-oxide)
(g) 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine (irgarol) (h) 3-iodo-2-propynyl butylcarbamate (IPBC) (i) 2-(n-octyl)-3(2H)-isothiazolone (OIT)
(j) 4,5-dichloro-2-(n-octyl)-3(2H)-isothiazolone (DCOIT) (k) 2,4,5,6-tetrachloro- 1 ,3-benzenedicarbonitrile (chlorothalonil) (1) 1 , l-dichloro-N-[(dimethylamino)sulfonyl]- 1-fluoro-N-phenyl- methanesulfenamide (dichlofluanid) (m) 1 , l-dichloro-N-[(dimethylamino)sulfonyl]- l-fluoro-N-(4-methylphenyl)- methanesulfenamide (tolylfluanid).
That is, they arrived at the perfection of this invention having discovered that by combining 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and the above compounds (a)-(m), one obtains antimicrobial compositions that are more effective, and have a wider antimicrobial spectrum, than if each compound is used singly.
This invention provides antimicrobial composition comprising 3-benzo[b]thiene-2-yl- 5,6-dihydro-l,4,2-oxathiazine-4-oxide and one or more of the following compounds (a)-(m):
(a) l-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene
(b) l-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene
(c) Zinc 2-pyridine thiol-1 -oxide
(d) Copper 2-pyridine thiol-1 -oxide
(e) 2-pyridine thiol-1-oxide sodium salt
(f) 2,2-dithio-bis(pyridine- 1-oxide)
(g) 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine (irgarol) (h) 3-iodo-2-propynyl butylcarbamate (IPBC)
(i) 2-(n-octyl)-3(2H)-isothiazolone (OIT)
(j) 4,5-dichloro-2-(n-octyl)-3(2H)-isothiazolone (DCOIT)
(k) 2,4,5,6-tetrachloro- 1 ,3-benzenedicarbonitrile (chlorothalonil)
(1) 1 , l-dichloro-N-[(dimethylamino)sulfonyl]- 1-fluoro-N-phenyl- methanesulfenamide (dichlofluanid)
(m) 1 , l-dichloro-N-[(dimethylamino)sulfonyl]- l-fluoro-N-(4-methylphenyl)- methanesulfenamide (tolylfluanid).
Preferably the weight ratio of above 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2- oxathiazine-4-oxide and above compounds (a)-(m) should be in the range 20:1 to 1:20. More preferably, the weight ratio of above 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2- oxathiazine-4-oxide and above compounds (a)-(m) should be in range 5:1 to 1:5.
The technical term "antimicrobial composition" used in this specification means a composition that has the effect of inhibiting the growth of bacteria, fungi, yeast, algae, etc. or killing these micro-organisms.
A. Composition of the invention A, JL. _ Effective co mponents The antimicrobial compositions of this invention comprise as its effective components 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and one or more of the following compounds (a)-(m):
(a) l-[[(3-iodo-2-propynyl)oxy]methoxy]4-methoxy benzene
(b) l-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene (c) Zinc 2-pyridine thiol-1 -oxide
(d) Copper 2-pyridine thiol- 1-oxide
(e) 2-pyridine thiol-1-oxide sodium salt
(f) 2,2-dithio-bis(pyridine- 1 -oxide)
(g) 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine (irgarol) (h) 3-iodo-2-ρroρynyl butylcarbamate (IPBC)
(i) 2-(n-octyl)-3(2H)-isothiazolone (OIT)
(j) 4,5-dichloro-2-(n-octyl)-3(2H)-isothiazolone (DCOIT)
(k) 2,4,5,6-tetrachloro- 1 ,3-benzenedicarbonitrile (chlorothalonil)
(1) 1 , l-dichloro-N-[(dimethylamino)sulfonyl]- 1 -fluoro-N-phenyl- methanesulfenamide (dichlofluanid)
(m) l,l-dichloro-N-[(dimethylamino)sulfonyl]-l-fluoro-N-(4-methylphenyl)- methanesulfenamide (tolylfluanid).
3-Benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide can be synthesized by, for example, the method described in JP-B2-2761441.
l-[[(3-Iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene can be synthesized by, for example, the method described in JP-B2-2852289.
l-Chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene can be synthesized by, for example, the method described in JP-B-47-24121.
Zinc 2-pyridine thiol- 1-oxide can be synthesized by, for example, the method described in US-A-3,583,999.
Copper 2-pyridine thiol- 1-oxide can be synthesized by, for example, the method described in JP-B2-3062825.
2-Pyridine thiol- 1-oxide sodium salt can be synthesized by, for example, the method described in US-A-4,396,766.
2,2-Dithio-bis(pyridine- 1-oxide) can be synthesized by, for example, the method described in US-A-3,892,760.
2-Methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine can be synthesized by, for example, the method described in DE-A-1914014.
The proportion between 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) in the antimicrobial compositions can be appropriately selected according to the types of target micro-organisms and the conditions under which above composition is to be used as an antimicrobial agent. Normally, the proportion between 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) is, in weight ratio, in the range 20:1 to 1:20, preferably 5:1 to 1:5, and especially preferably 3:1 to 1:3.
The antimicrobial compositions of this invention can be used in a form that fits its purpose of use. For example, the antimicrobial compositions of this invention may be
simply a mixture of 3-benzo[bjthiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m), but preferably it can include, besides 3-benzo[b]thiene-2-yl-5,6- dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m), an appropriate solvent and dispersant or carrier or other component.
The total content of 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) in the composition of this invention varies with the product form and purpose of use, etc., but usually it is 0.1% by weight to 95% by weight, and preferably 0.2% by weight to 60% by weight, of the total antimicrobial compositions that is obtained.
The amount of the antimicrobial compositions of this invention to use varies with the composition and the type and concentration of the micro-organisms on which it is to be used, but generally, if it is to be used on fibre, paint, adhesive, etc., a good effect is obtained at about 1 - 10, 000 g/kg.
A.2_. _ S lvents_and disper s ant s.
If the system in which it is to be used is an industrial water system of any of various types, in consideration of the dissolvability and dispersibility of the effective components and other factors, it is desirable to prepare a liquid formulation that includes a solvent and dispersant, as discussed below.
As the solvent that can be used in the antimicrobial compositions of this invention, one may cite any solvent that does not adversely affect the active ingredients, for example, water, alcohols (for example, methyl alcohol, ethyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, glycerin, etc.), ketones (for example, acetone, methyl ethyl ketone, etc.), ethers (for example, dioxane, tetrahydrofurane, cellosolve, diethylene glycol dimethyl ether, etc.), aliphatic hydrocarbons (for example, hexane, kerosene, etc.), aromatic hydrocarbons (for example, benzene, toluene, xylene, solvent naphtha, methyl naphthalene, etc.), halogenated hydrocarbons (for example, chloroform, carbon tetrachloride, etc.), acid amides (for example, dimethyl formadide, etc.), esters (for example, methyl acetate ester, ethyl acetate ester, butyl acetate ester, fatty acid glycerin ester, etc.), and nitrols (for example, acetonitrile, etc.). These solvents may be used either singly or in combination of two or more species.
As the dispersant that can be used in the antimicrobial compositions of this invention, one may cite any dispersant that does not adversely affect the active ingredients, for example, a surfactant. As such surfactants, one may cite soaps, high-grade alcohol
sulfate ester, alkylsulfonic acid, alkyl allyl sulfonic acid, quaternary ammonium salt, oxyalkyl amine, fatty acid ester, polyalkylene oxide compounds, anhydrosorbitol compounds, etc. These dispersants may be used either singly or in combination of two or more species.
A._3_._ Carriers
As the carrier that can be used in the antimicrobial compositions of this invention, one may cite any dispersant that does not adversely affect the active ingredients, for example, clays (for example, kaolin, bentonite, acid clay, etc.), talcs (for example, talc powder, agalmatolite powder, etc.), silicas (for example, diatomaceous earth, silicic acid anhydride, mica powder, etc.), alumina, sulfur powder, activated charcoal, etc.
These carriers may be used either singly or in combination of two or more species.
AA _ Other components The antimicrobial compositions of this invention may also contain other antimicrobial agents (for example, organic chlorine-based biocides, organic phosphorus-based biocides, organic iodine-based biocides, organic sulfur-based biocides, organic nitrogen-based biocides, organic nitrogen-sulfur-based biocides, benzimidazole-based biocides, phenol-based biocides, organic acid ester-based biocides, antibiotics, etc.), insecticides (for example, natural insecticides, carbamate-based insecticides, organic phosphor-based insecticides, etc.), adjuvants (for example, casein, gelatin, starch, alginic acid, agar, CMC, polyvinyl alcohol, vegetable oil, bentonite, cresol soap, etc.), degradation prevention agents, scents etc.
The antimicrobial compositions of the present invention may optionally further comprise quaternary ammonium salts such as quaternary ammonium salts of the trimethyl alkyl ammonium halide type, e.g. trimethyl decyl ammonium chloride, trimethyl dodecylammonium chloride, trimethyl tallow ammonium chloride, trimethyl oleyl ammonium chloride; or of the dimethyl alkyl benzyl ammonium type, e.g. dimethyl decyl benzyl ammonium chloride, dimethyldo decyl benzyl ammonium chloride, dimethyl hexadecylbenzyl ammonium chloride (commonly designated as "cetalkonium chloride"), dimethyl octadecyl benzyl ammonium chloride, dimethyl coco benzyl ammonium chloride, dimethyl tallow benzyl ammonium chloride; and particularly the dimethyl Cg.^alkyl benzyl ammonium chloride mixture which is commonly known as "benzalkonium chloride" ; dimethyl dialkyl ammonium halides, e.g. dimethyl dioctyl ammonium chloride, dimethyl didecyl ammonium chloride, dimethyl didodecyl ammonium chloride, dimethyl dicoco ammonium chloride, dimethyl ditallow ammonium chloride, dimethyl octyl decyl ammonium chloride,
dimethyl dodecyl octyl ammonium chloride, dimethyl dihydrogenated tallow ammonium chloride.
B. Target organisms The antimicrobial compositions of this invention are generally widely effective against bacteria, fungi, yeast, algae, etc., and it has an antimicrobial spectrum that is broader than that of antimicrobial compositions obtained by prescribing 3-benzo[b]thiene-2-yl- 5,6-dihydro-l,4,2-oxathiazine-4-oxide or any of the compounds (a)-(m) singly. The antimicrobial compositions are inhibiting the growth or killing against the following organisms; bacteria such as Bacillus, Staphylococcus, Enterobacter, Escherichia, Pseudomonas, etc., fungi such as Aspergillus, Aureobasidium, Chaetomium, Cladosporium, Gliocladium, Penicillium, Trichoderma, etc., yeasts such as Candida, Rhodotorula, etc., and algae such as Chlorella, Trentepohlia, Nostoc, Phormidium, etc.
The antimicrobial compositions of this invention may be applied to various industrial products and industrial raw materials. As such various industrial products and industrial raw materials, one may cite fiber, paint, adhesive, wood, leather, processed paper products, electronic components, wall materials, resin moldings, etc.
Working examples
By the following working examples, we describe in greater detail the antimicrobial effectiveness of the antimicrobial compositions of this invention. The term "MIC" as used in these working examples refers to the minimum inhibitory concentration (ppm) of the active ingredient in the antimicrobial compositions. More specifically, it refers to the minimum concentration of the mixture of 3-benzo[b]thiene-2-yl-5,6-dihydro- 1 ,4,2-oxathiazine-4-oxide and compounds (a)-(m) in the antimicrobial compositions that is able to inhibit the growth of bacteria, fungi or algae.
Preparing. bacteιial_s spensions for inoculation The bacterial suspensions for inoculation used in working example 1 were prepared as follows. Two bacteria, Staphylococcus aureus IFO 12732 and Escherichia coli IFO 3972, where inoculated respectively into two separate nutrient broth culture media, they were shake-cultured for 4-6 hours at 30°C, and two bacterial suspensions for inoculation were thus prepared.
Preparing, spore suspensions _f r inoculation
The spore suspensions for inoculation used in working example 2 were prepared as follows. Two fungi, Aspergillus niger IFO 6341 and Penicillium funiculosum IFO
6345, were cultured on two potato dextrose agar culture media not containing any biocides, and spores were formed. Next, said fungus spores were dispersed in disinfectant water to which 0.005% lubricant had been added, and two spore suspensions for inoculation were thus prepared.
Pjeparmg. alg.ae_sιsriensions forjnoculation
The algae suspensions for inoculation used in working example 3 were prepared as follows. Bold's Basal liquid culture medium (50 ml) was inoculated with Chlorella pyrenoidosa NIES 226, it was shake-cultured for 14 days at 25°C, and algae suspensions for inoculation was thus prepared.
W jking example.1
Antimicrobial compositions were prepared by adding 3-benzo[b]thiene-2-yl-5,6- dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) to dimethyl sulfoxide in the weight ratios listed in Tables 1 and 2 below. Next, test culture media were prepared by adding each of the varying diluted aqueous solutions (0.2 ml) of the antimicrobial compositions to a nutrient broth culture medium (10 ml). Each of these test culture media was inoculated with the above bacterial suspensions for inoculation (0.1 ml), and after culturing for 24 hours at 30°C. Then, the presence or absence of bacteria growth was assessed by visually observing the turbidity of the culture medium. The minimum concentration of mixture of 3-benzo[b]thiene-2-yl-5,6-dihydro-l ,4,2- oxathiazine-4-oxide and compounds (a)-(m) that was able to inhibit the growth of bacteria in the culture medium was taken as the MIC. Tables 1 and 2 list the MIC, for each bacterium, of the antimicrobial compositions of each weight ratio.
[Table 1]
Note: Compound A: 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide
Working exampl_e_2 Antimicrobial compositions were prepared by adding 3-benzo[b]thiene-2-y 1-5,6- dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) to dimethyl sulfoxide in the weight ratios listed in Tables 3 and 4 below. Next, test culture media were prepared by adding each of the varying diluted aqueous solutions (0.3 ml) of these antimicrobial compositions to a potato dextrose agar culture medium (15 ml). Each of these test culture media was inoculated with the above spore suspensions for inoculation (1 ml), and after culturing for 7 days at 28°C. Then, the presence or absence of fungus growth on each culture medium was observed visually. The minimum concentration of mixture of 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)- (m) that was able to inhibit the growth of fungi on the culture medium was taken as the MIC. Tables 3 and 4 list the MIC, for each fungus, of the antimicrobial composition of each weight ratio.
[Table 3]
Note: Compound A: 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide
[Table 4]
Working example_3 Antimicrobial compositions were prepared by adding 3-benzo[b]thiene-2-yl-5,6- dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) to dimethyl sulfoxide in the weight ratios listed in Table 5 below. Next, test culture media were prepared by adding each of the varying diluted aqueous solutions (0.1 ml) of these antimicrobial compositions to Bold's Basal agar culture medium (15 ml). Each of these test culture media was inoculated with the above algae suspensions for inoculation (1 ml), and after culturing for 14 days at 25°C and 1500 lux. Then, the presence or absence of algae growth on each culture medium was observed visually. The minimum concentration of mixture of 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and compounds (a)-(m) that was able to inhibit the growth of algae on the culture medium was taken as the MIC. Table 5 lists the MIC, for algae, of the antimicrobial composition of each weight ratio.
[Table 5]
Note: Compound A: 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide
The results shown in Tables 1-5 show that the antimicrobial compositions of this invention, due to the synergistic effect of its active ingredients, have greater effectiveness and a broader antimicrobial spectrum than previous antimicrobial compositions. They also show that the concentration of an antimicrobial composition used for suppressing the same amount of bacteria, fungi, or algae is kept much lower than if an active ingredient is used singly.
Effects of the invention This invention yields antimicrobial compositions comprising as their active ingredients 3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and one or more selected from
(a) l-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene,
(b) l-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene, (c) Zinc 2-pyridine thiol- 1-oxide,
(d) Copper 2-pyridine thiol- 1 -oxide,
(e) 2-pyridine thiol- 1-oxide sodium salt,
(f) 2,2-dithio-bis(pyridine-l-oxide),
(g) 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine (irgarol), (h) 3-iodo-2-ρropynyl butylcarbamate (IPBC),
(i) 2-(n-octyl)-3(2H)-isothiazolone (OIT), or
(j) 4,5-dichloro-2-(n-octyl)-3(2H)-isothiazolone (DCOIT)
(k) 2,4,5,6-tetrachloro-l,3-benzenedicarbonitrile (chlorothalonil)
(1) 1 , l-dichloro-N-[(dimethylamino)sulfonyl]~ 1-fluoro-N-phenyl- methanesulfenamide (dichlofluanid)
(m) l,l-dichloro-N-[(dimethylamino)sulfonyl]-l-fluoro-N-(4-methylphenyl)- methanesulf enamide (tolylfluanid) .
Combining these active ingredients produces a synergistic effect of these components and provides antimicrobial compositions that are highly safe, are high effective, and have a broad antimicrobial spectrum. Furthermore, because the concentration of the active ingredients contained in the antimicrobial compositions of this invention is kept low, it can be prepared at very low cost and has little effect on the environment. The antimicrobial compositions of this invention are effective for antibacterial, antifungal and antialgal purposes on various industrial products and industrial raw materials.
Claims (10)
1. An antimicrobial composition comprising 3-benzo[b]thiene-2-yl-5,6-dihydro- l,4,2-oxathiazine-4-oxide and one or more of the following compounds (a) l-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene,
(b) l-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene,
(c) zinc 2-pyridine thiol- 1-oxide,
(d) copper 2-pyridine thiol- 1 -oxide,
(e) 2-pyridine thiol- 1 -oxide sodium salt, (f) 2,2-dithio-bis(pyridine- 1-oxide),
(g) 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine,
(h) 3-iodo-2-propynyl butylcarbamate,
(i) 2-(n-octyl)-3(2H)-isothiazolone,
(j) 4,5-dichloro-2-(n-octyl)-3(2H)-isothiazolone, (k) 2,4,5, 6-tetrachloro-l,3-benzenedicarbonitrile,
(1) 1,1 -dichloro-N- [(dimethylamino) sulf ony 1]- 1 -fluoro-N-phenyl- mefhanesulfenamide, or
(m) l,l-dichloro-N-[(dimethylamino)sulfonyl]-l-fluoro-N-(4-methylphenyl)- methanesulf enamide .
2. An antimicrobial composition as claimed in claim 1 comprising
3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and one or more of the following compounds
(a) l-[[(3-iodo-2-propynyl)oxy]methoxy]-4-methoxy benzene, (b) l-chloro-4-[[(3-iodo-2-propynyl)oxy]methoxy] benzene,
(c) zinc 2-pyridine thiol- 1-oxide,
(d) copper 2-pyridine thiol- 1-oxide,
(e) 2-pyridine thiol-1-oxide sodium salt,
(f) 2,2-dithio-bis(pyridine- 1-oxide), (g) 2-methylthio-4-t-butyl amino-6-cyclopropyl amino-s-triazine,
(h) 3-iodo-2-propynyl butylcarbamate, or
(i) 2-(n-octyl)-3(2H)-isothiazolone,
(j) 4,5-dichloro-2-(n-octyl)-3(2H)-isothiazolone,
(k) 2,4,5,6-tetrachloro- 1 ,3-benzenedicarbonitrile, (1) 1, l-dichloro-N-[(dimethylamino)sulfonyl]-l-fluoro-N-phenyl- methanesulfenamide, or (m) l,l-dichloro-N-[(dimethylamino)sulfonyl]-l-fluoro-N-(4-methylphenyl)- methanesulfenamide, in quantities producing a mutual synergistic antimicrobial effect.
3. A composition according to any of claims 1 or 2 wherein the weight ratio of
3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and the compounds (a)-(m) is in the range 20:1 to 1:20.
4. A composition according to claim 3 wherein the weight ratio of 3-benzo[b]thiene-2- yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and the compounds (a)-(m) is in the range
5:1 to 1:5.
5. A composition according claim 4 wherein the weight ratio of 3-benzo[b]thiene-2- yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and the compounds (a)-(m) is in the range 3:1 to 1:3.
6. A composition according to any of claims 1 or 2 wherein the total content of
3-benzo[b]thiene-2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and the compounds
(a)-(m) is in the range of 0.1% by weight to 95%.
7. A composition according to claim 6 wherein the total content of 3-benzo[b]thiene- 2-yl-5,6-dihydro-l,4,2-oxathiazine-4-oxide and the compounds (a)-(m) is in the range of 0.2% by weight to 60% by weight.
8. Use of a composition as claimed in any of claims 1 to 7 to protect materials against bacteria, fungi, yeast and algae.
9. A method of protecting materials against bacteria, fungi, yeast, and algae, wherein the said method comprises administration or application of a composition according to any of claims 1 to 7.
10. A process for preparing a composition as claimed in any of claims 1 to 7, characterized in that the active ingredients are intimately mixed with each other.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001-61158 | 2001-03-06 | ||
| JP2001061158A JP2002265310A (en) | 2001-03-06 | 2001-03-06 | Antimicrobial agent composition |
| PCT/EP2002/002368 WO2002076209A2 (en) | 2001-03-06 | 2002-03-04 | Antimicrobial compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002302387A1 true AU2002302387A1 (en) | 2003-03-27 |
| AU2002302387B2 AU2002302387B2 (en) | 2006-08-31 |
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|---|---|---|---|
| AU2002302387A Ceased AU2002302387B2 (en) | 2001-03-06 | 2002-03-04 | Antimicrobial compositions |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7416736B2 (en) |
| EP (1) | EP1367894B1 (en) |
| JP (1) | JP2002265310A (en) |
| KR (2) | KR100858023B1 (en) |
| CN (3) | CN1286371C (en) |
| AT (1) | ATE395829T1 (en) |
| AU (1) | AU2002302387B2 (en) |
| BR (1) | BR0207849A (en) |
| CA (3) | CA2768012A1 (en) |
| CZ (1) | CZ20032652A3 (en) |
| DE (1) | DE60226708D1 (en) |
| DK (1) | DK1367894T3 (en) |
| EA (1) | EA006167B1 (en) |
| ES (1) | ES2306767T3 (en) |
| HU (1) | HUP0303462A3 (en) |
| IL (2) | IL157752A0 (en) |
| MX (1) | MXPA03008091A (en) |
| NO (1) | NO330536B1 (en) |
| NZ (1) | NZ528466A (en) |
| PL (2) | PL204663B1 (en) |
| SK (1) | SK287813B6 (en) |
| WO (1) | WO2002076209A2 (en) |
| ZA (1) | ZA200306927B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60305844T2 (en) * | 2002-11-22 | 2007-05-16 | Rohm And Haas Co. | Aqueous dispersion of low melting point organic solids |
| US8124635B2 (en) * | 2006-06-12 | 2012-02-28 | Rohm And Haas Company | Antimicrobial composition useful for preserving wood |
| EP2153722A1 (en) * | 2008-08-05 | 2010-02-17 | Lanxess Deutschland GmbH | Antifungal liquid formulations containing 3-iodopropynylbutylcarbamate (IPBC) and N-octyl isothiazolinone (NOIT) |
| CN104073333B (en) * | 2013-03-29 | 2019-05-28 | 上海德润宝特种润滑剂有限公司 | Water-ethylene glycol nonflame hydraulic fluid and preparation method thereof |
| JP6125400B2 (en) * | 2013-10-21 | 2017-05-10 | 株式会社ピュアソン | Antibacterial treatment method and antibacterial agent |
| CN110839633B (en) * | 2019-08-30 | 2021-04-30 | 苏州科技大学 | Antibacterial application of 2-mercaptopyridine-N-oxide trivalent cobalt salt complex |
| CN117604531A (en) * | 2023-11-07 | 2024-02-27 | 嘉兴顺诚精细化工有限公司 | A kind of water-soluble non-emulsified tempering and rust-proof liquid and preparation method |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH492400A (en) * | 1968-03-20 | 1970-06-30 | Agripat Sa | Selective herbicide and its use for combating weeds and grass weeds |
| US3583999A (en) * | 1968-11-01 | 1971-06-08 | Procter & Gamble | Process for preparing 2-pyridinethiol n-oxides and derivatives thereof |
| US3892760A (en) * | 1974-05-02 | 1975-07-01 | Olin Corp | Bis-(2-pyridyl-1-oxide) disulfide |
| US4396766A (en) * | 1982-04-28 | 1983-08-02 | Olin Corporation | Process for producing sodium and zinc pyrithione |
| MY137123A (en) * | 1993-08-24 | 2008-12-31 | Uniroyal Chem Co Inc | Wood preservative oxathiazines |
| ZA946449B (en) * | 1993-08-24 | 1996-02-26 | Janssen Pharmaceutica Nv | Antibacterial and antifouling oxathiazines and their oxides |
| US5540860A (en) * | 1994-02-28 | 1996-07-30 | Olin Corporation | Process for preparing copper pyrithione |
| JP2852289B2 (en) * | 1997-02-26 | 1999-01-27 | 長瀬産業株式会社 | Iodopropargyl derivative and antimicrobial agent containing the derivative as active ingredient |
| JP2001519365A (en) | 1997-10-15 | 2001-10-23 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Synergistic composition comprising oxathiazine and benzothiophene-2-carboxamide-S, S-dioxide |
| JP4018788B2 (en) | 1998-01-30 | 2007-12-05 | 日本エンバイロケミカルズ株式会社 | Industrial fungicide |
| JP4177923B2 (en) * | 1998-08-04 | 2008-11-05 | 日本エンバイロケミカルズ株式会社 | Industrial fungicide |
| GB9826245D0 (en) | 1998-11-30 | 1999-01-20 | Hickson Int Plc | Wood preserative formulations |
| JP2000191412A (en) * | 1998-12-28 | 2000-07-11 | Nagase Kasei Kogyo Kk | Microbicidal composition |
| JP2000302601A (en) | 1999-02-17 | 2000-10-31 | Takeda Chem Ind Ltd | Industrial microbiocide |
| JP2000273003A (en) * | 1999-03-19 | 2000-10-03 | Nagase Kasei Kogyo Kk | Antimicrobial agent composition |
| JP2001213708A (en) * | 2000-01-27 | 2001-08-07 | Nagase Kasei Kogyo Kk | Antimicrobial composition |
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2001
- 2001-03-06 JP JP2001061158A patent/JP2002265310A/en active Pending
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2002
- 2002-03-04 ES ES02729958T patent/ES2306767T3/en not_active Expired - Lifetime
- 2002-03-04 KR KR1020087004941A patent/KR100858023B1/en not_active Expired - Fee Related
- 2002-03-04 CA CA2768012A patent/CA2768012A1/en not_active Abandoned
- 2002-03-04 PL PL363567A patent/PL204663B1/en not_active IP Right Cessation
- 2002-03-04 EA EA200300975A patent/EA006167B1/en not_active IP Right Cessation
- 2002-03-04 CA CA2436239A patent/CA2436239C/en not_active Expired - Fee Related
- 2002-03-04 CN CNB028060466A patent/CN1286371C/en not_active Expired - Fee Related
- 2002-03-04 US US10/469,772 patent/US7416736B2/en not_active Expired - Fee Related
- 2002-03-04 SK SK1225-2003A patent/SK287813B6/en not_active IP Right Cessation
- 2002-03-04 CN CNB2005100035726A patent/CN100339003C/en not_active Expired - Fee Related
- 2002-03-04 MX MXPA03008091A patent/MXPA03008091A/en active IP Right Grant
- 2002-03-04 NZ NZ528466A patent/NZ528466A/en not_active IP Right Cessation
- 2002-03-04 AU AU2002302387A patent/AU2002302387B2/en not_active Ceased
- 2002-03-04 AT AT02729958T patent/ATE395829T1/en not_active IP Right Cessation
- 2002-03-04 DE DE60226708T patent/DE60226708D1/en not_active Expired - Lifetime
- 2002-03-04 HU HU0303462A patent/HUP0303462A3/en unknown
- 2002-03-04 DK DK02729958T patent/DK1367894T3/en active
- 2002-03-04 CN CN200710129011XA patent/CN101081027B/en not_active Expired - Fee Related
- 2002-03-04 EP EP02729958A patent/EP1367894B1/en not_active Expired - Lifetime
- 2002-03-04 WO PCT/EP2002/002368 patent/WO2002076209A2/en not_active Ceased
- 2002-03-04 BR BR0207849-0A patent/BR0207849A/en not_active Application Discontinuation
- 2002-03-04 KR KR1020037010089A patent/KR100822676B1/en not_active Expired - Fee Related
- 2002-03-04 CA CA2768005A patent/CA2768005A1/en not_active Abandoned
- 2002-03-04 CZ CZ20032652A patent/CZ20032652A3/en unknown
- 2002-03-04 PL PL388366A patent/PL209038B1/en not_active IP Right Cessation
- 2002-04-03 IL IL15775202A patent/IL157752A0/en unknown
-
2003
- 2003-09-04 IL IL157752A patent/IL157752A/en not_active IP Right Cessation
- 2003-09-04 ZA ZA200306927A patent/ZA200306927B/en unknown
- 2003-09-05 NO NO20033935A patent/NO330536B1/en not_active IP Right Cessation
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