JP6250656B2 - 水含有システムにおける抗微生物用複素環式化合物の使用 - Google Patents
水含有システムにおける抗微生物用複素環式化合物の使用 Download PDFInfo
- Publication number
- JP6250656B2 JP6250656B2 JP2015518452A JP2015518452A JP6250656B2 JP 6250656 B2 JP6250656 B2 JP 6250656B2 JP 2015518452 A JP2015518452 A JP 2015518452A JP 2015518452 A JP2015518452 A JP 2015518452A JP 6250656 B2 JP6250656 B2 JP 6250656B2
- Authority
- JP
- Japan
- Prior art keywords
- oxazolo
- compound
- pyridine
- tetrahydro
- alkyl
- 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.)
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 35
- 230000000845 anti-microbial effect Effects 0.000 title description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 44
- 244000005700 microbiome Species 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000012530 fluid Substances 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 6
- -1 heptan-3-yl Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- AHYITDFVMVPOTB-UHFFFAOYSA-N 2,3,4,8,9,9a-hexahydropyrido[2,1-b][1,3]oxazine Chemical compound C1CC=CN2CCCOC21 AHYITDFVMVPOTB-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- HOYUUPHKURKGKU-UHFFFAOYSA-N 2-butyl-3-ethyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine Chemical compound CCCCC1OC2CCC=CN2C1CC HOYUUPHKURKGKU-UHFFFAOYSA-N 0.000 claims description 3
- JOSKBROZGUSOGM-UHFFFAOYSA-N 2-ethyl-2,3,4,8,9,9a-hexahydro-1H-pyrido[1,2-a]pyrimidine Chemical compound CCC1CCN2C=CCCC2N1 JOSKBROZGUSOGM-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000004566 building material Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 238000005553 drilling Methods 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000004816 latex Substances 0.000 claims description 2
- 229920000126 latex Polymers 0.000 claims description 2
- 239000002332 oil field water Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- VDEVQYAWDDJMMR-UHFFFAOYSA-N 2,3-dimethyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine Chemical compound CC1OC2CCC=CN2C1C VDEVQYAWDDJMMR-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- WDLXYSDSOHEMHO-UHFFFAOYSA-N 3,3-dimethyl-2,7,8,8a-tetrahydro-[1,3]oxazolo[3,2-a]pyridine Chemical compound CC1(C)COC2CCC=CN12 WDLXYSDSOHEMHO-UHFFFAOYSA-N 0.000 claims 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000003754 machining Methods 0.000 claims 1
- 238000005096 rolling process Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- 239000013058 crude material Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 241001148470 aerobic bacillus Species 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VDPLLINNMXFNQX-UHFFFAOYSA-N (1-aminocyclohexyl)methanol Chemical compound OCC1(N)CCCCC1 VDPLLINNMXFNQX-UHFFFAOYSA-N 0.000 description 2
- VQKGBMGKTMVKPX-UHFFFAOYSA-N 2-amino-4-ethyloctan-3-ol Chemical compound CCCCC(CC)C(O)C(C)N VQKGBMGKTMVKPX-UHFFFAOYSA-N 0.000 description 2
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 description 2
- AHZILZSKKSPIKM-UHFFFAOYSA-N 3-aminooctan-4-ol Chemical compound CCCCC(O)C(N)CC AHZILZSKKSPIKM-UHFFFAOYSA-N 0.000 description 2
- 241000203069 Archaea Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- YPQYWQXZLFLCRZ-UHFFFAOYSA-N 2-amino-4-propan-2-ylheptan-3-ol Chemical compound CCCC(C(C)C)C(O)C(C)N YPQYWQXZLFLCRZ-UHFFFAOYSA-N 0.000 description 1
- ZFLTXZOXWZTJJJ-UHFFFAOYSA-N 2-heptan-3-yl-3-methyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine Chemical compound CCCCC(CC)C1OC2CCC=CN2C1C ZFLTXZOXWZTJJJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- PLXBWHJQWKZRKG-UHFFFAOYSA-N Resazurin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3[N+]([O-])=C21 PLXBWHJQWKZRKG-UHFFFAOYSA-N 0.000 description 1
- 241000589499 Thermus thermophilus Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960000587 glutaral Drugs 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005098 hot rolling Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261661518P | 2012-06-19 | 2012-06-19 | |
| US61/661,518 | 2012-06-19 | ||
| PCT/US2013/045418 WO2013191988A1 (en) | 2012-06-19 | 2013-06-12 | Heterocyclic antimicrobial compounds for use in water - containing systems |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015523358A JP2015523358A (ja) | 2015-08-13 |
| JP2015523358A5 JP2015523358A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2017-11-16 |
| JP6250656B2 true JP6250656B2 (ja) | 2017-12-20 |
Family
ID=48692677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015518452A Active JP6250656B2 (ja) | 2012-06-19 | 2013-06-12 | 水含有システムにおける抗微生物用複素環式化合物の使用 |
Country Status (12)
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198697B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-09-11 | 1975-09-12 | Roussel Uclaf | |
| US5480643A (en) | 1991-10-16 | 1996-01-02 | Ecolab Inc. | Stable antimicrobial dialdehyde composition and methods of use |
| US6034138A (en) | 1995-11-21 | 2000-03-07 | Block Drug Company, Inc. | Disinfectant composition |
| US7319131B2 (en) | 2003-03-07 | 2008-01-15 | Angus Chemical Company | Phenolic resins |
| US20040152749A1 (en) * | 2003-02-04 | 2004-08-05 | Isp Investments Inc. | Antimicrobial oxazolidine/iodopropynyl-butyl carbamate composition containing less than 0.1 wt%free formaldehyde |
| EP2038226A1 (en) | 2006-07-05 | 2009-03-25 | Ciba Holding Inc. | Dihalogeno-hydroxydiphenylether as antimicrobials in water treatment |
| US20100078393A1 (en) | 2008-10-01 | 2010-04-01 | Bei Yin | Biocidal compositions and methods of use |
| EP2629608B1 (en) | 2010-12-17 | 2016-07-13 | Dow Global Technologies LLC | Protected antimicrobial compounds for high temperature applications |
| US8741928B2 (en) | 2010-12-17 | 2014-06-03 | Dow Global Technologies Llc | Protected antimicrobial compounds for high temperature applications |
-
2013
- 2013-06-12 WO PCT/US2013/045418 patent/WO2013191988A1/en active Application Filing
- 2013-06-12 IN IN10069DEN2014 patent/IN2014DN10069A/en unknown
- 2013-06-12 JP JP2015518452A patent/JP6250656B2/ja active Active
- 2013-06-12 PL PL13731226.0T patent/PL2861592T3/pl unknown
- 2013-06-12 RU RU2014153679A patent/RU2656592C2/ru active
- 2013-06-12 EP EP13731226.0A patent/EP2861592B1/en active Active
- 2013-06-12 BR BR112014030571-4A patent/BR112014030571B1/pt active IP Right Grant
- 2013-06-12 AU AU2013277511A patent/AU2013277511B2/en not_active Ceased
- 2013-06-12 CN CN201380032241.8A patent/CN104603135B/zh active Active
- 2013-06-12 US US14/565,867 patent/US9617278B2/en active Active
- 2013-06-12 CA CA2876015A patent/CA2876015C/en active Active
- 2013-06-14 AR ARP130102105 patent/AR091452A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| AU2013277511B2 (en) | 2017-05-18 |
| RU2014153679A (ru) | 2016-08-10 |
| BR112014030571B1 (pt) | 2019-04-16 |
| PL2861592T3 (pl) | 2016-09-30 |
| RU2656592C2 (ru) | 2018-06-06 |
| US9617278B2 (en) | 2017-04-11 |
| CA2876015C (en) | 2020-01-07 |
| AR091452A1 (es) | 2015-02-04 |
| EP2861592B1 (en) | 2016-04-06 |
| BR112014030571A2 (pt) | 2017-07-25 |
| EP2861592A1 (en) | 2015-04-22 |
| CA2876015A1 (en) | 2013-12-27 |
| US20150336983A1 (en) | 2015-11-26 |
| CN104603135A (zh) | 2015-05-06 |
| IN2014DN10069A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-08-14 |
| WO2013191988A1 (en) | 2013-12-27 |
| AU2013277511A1 (en) | 2015-01-15 |
| CN104603135B (zh) | 2016-10-05 |
| JP2015523358A (ja) | 2015-08-13 |
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| Publication | Publication Date | Title |
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| JP6250655B2 (ja) | 抗微生物化合物 | |
| JP6250656B2 (ja) | 水含有システムにおける抗微生物用複素環式化合物の使用 | |
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