CN104603135B - 用于含水体系的杂环抗微生物化合物 - Google Patents
用于含水体系的杂环抗微生物化合物 Download PDFInfo
- Publication number
- CN104603135B CN104603135B CN201380032241.8A CN201380032241A CN104603135B CN 104603135 B CN104603135 B CN 104603135B CN 201380032241 A CN201380032241 A CN 201380032241A CN 104603135 B CN104603135 B CN 104603135B
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- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- 125000000623 heterocyclic group Chemical group 0.000 title description 2
- 244000005700 microbiome Species 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 239000012530 fluid Substances 0.000 claims description 14
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000004659 sterilization and disinfection Methods 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000002173 cutting fluid Substances 0.000 claims description 2
- 238000005553 drilling Methods 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 238000005098 hot rolling Methods 0.000 claims description 2
- 239000004816 latex Substances 0.000 claims description 2
- 229920000126 latex Polymers 0.000 claims description 2
- 239000007788 liquid Substances 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
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 230000000474 nursing effect Effects 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 230000000630 rising effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- 239000000376 reactant Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 239000003345 natural gas Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 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 4
- 230000000694 effects Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- -1 suberyl Chemical group 0.000 description 3
- VDPLLINNMXFNQX-UHFFFAOYSA-N (1-aminocyclohexyl)methanol Chemical compound OCC1(N)CCCCC1 VDPLLINNMXFNQX-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
- 241000589499 Thermus thermophilus Species 0.000 description 2
- 241001148470 aerobic bacillus Species 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241000203069 Archaea Species 0.000 description 1
- 241000697872 Bactria Species 0.000 description 1
- TTYMFELKEYOSIK-UHFFFAOYSA-N CNC1NC=CCC1 Chemical compound CNC1NC=CCC1 TTYMFELKEYOSIK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- 241000605716 Desulfovibrio Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 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 1
- 101000905241 Mus musculus Heart- and neural crest derivatives-expressed protein 1 Proteins 0.000 description 1
- 101001031591 Mus musculus Heart- and neural crest derivatives-expressed protein 2 Proteins 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000002053 acidogenic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000000872 buffer Substances 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
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 230000007423 decrease Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography 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
- 125000001183 hydrocarbyl group Chemical group 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
- 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
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000013102 re-test Methods 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000001629 suppression Effects 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
- 238000010998 test method Methods 0.000 description 1
- 238000007725 thermal activation Methods 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
-
- 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
- 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
-
- 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 (2)
| Publication Number | Publication Date |
|---|---|
| CN104603135A CN104603135A (zh) | 2015-05-06 |
| CN104603135B true CN104603135B (zh) | 2016-10-05 |
Family
ID=48692677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380032241.8A Active CN104603135B (zh) | 2012-06-19 | 2013-06-12 | 用于含水体系的杂环抗微生物化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9617278B2 (enExample) |
| EP (1) | EP2861592B1 (enExample) |
| JP (1) | JP6250656B2 (enExample) |
| CN (1) | CN104603135B (enExample) |
| AR (1) | AR091452A1 (enExample) |
| AU (1) | AU2013277511B2 (enExample) |
| BR (1) | BR112014030571B1 (enExample) |
| CA (1) | CA2876015C (enExample) |
| IN (1) | IN2014DN10069A (enExample) |
| PL (1) | PL2861592T3 (enExample) |
| RU (1) | RU2656592C2 (enExample) |
| WO (1) | WO2013191988A1 (enExample) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198697B1 (enExample) * | 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 |
| JP2009541046A (ja) * | 2006-07-05 | 2009-11-26 | チバ ホールディング インコーポレーテッド | 水処理における抗菌剤としてのジハロゲノ−ヒドロキシジフェニルエーテル |
| US20100078393A1 (en) * | 2008-10-01 | 2010-04-01 | Bei Yin | Biocidal compositions and methods of use |
| WO2012082404A1 (en) | 2010-12-17 | 2012-06-21 | Angus Chemical Company | Protected antimicrobial compounds for high temperature applications |
| CN103260404B (zh) | 2010-12-17 | 2015-04-01 | 陶氏环球技术有限公司 | 用于高温应用的受保护的抗微生物化合物 |
-
2013
- 2013-06-12 CA CA2876015A patent/CA2876015C/en active Active
- 2013-06-12 AU AU2013277511A patent/AU2013277511B2/en not_active Ceased
- 2013-06-12 RU RU2014153679A patent/RU2656592C2/ru active
- 2013-06-12 JP JP2015518452A patent/JP6250656B2/ja active Active
- 2013-06-12 EP EP13731226.0A patent/EP2861592B1/en active Active
- 2013-06-12 IN IN10069DEN2014 patent/IN2014DN10069A/en unknown
- 2013-06-12 US US14/565,867 patent/US9617278B2/en active Active
- 2013-06-12 WO PCT/US2013/045418 patent/WO2013191988A1/en not_active Ceased
- 2013-06-12 BR BR112014030571-4A patent/BR112014030571B1/pt active IP Right Grant
- 2013-06-12 PL PL13731226.0T patent/PL2861592T3/pl unknown
- 2013-06-12 CN CN201380032241.8A patent/CN104603135B/zh active Active
- 2013-06-14 AR ARP130102105 patent/AR091452A1/es active IP Right Grant
Non-Patent Citations (1)
| Title |
|---|
| R. A. LANODALE-SMITH.A Facile Synthesis of New Heterocycles from Glutaraldehyde.《J. Org. Chem.》.1971,第36卷(第1期),226-227. * |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014030571B1 (pt) | 2019-04-16 |
| RU2014153679A (ru) | 2016-08-10 |
| BR112014030571A2 (pt) | 2017-07-25 |
| RU2656592C2 (ru) | 2018-06-06 |
| AU2013277511A1 (en) | 2015-01-15 |
| AU2013277511B2 (en) | 2017-05-18 |
| PL2861592T3 (pl) | 2016-09-30 |
| JP2015523358A (ja) | 2015-08-13 |
| JP6250656B2 (ja) | 2017-12-20 |
| US20150336983A1 (en) | 2015-11-26 |
| CA2876015C (en) | 2020-01-07 |
| US9617278B2 (en) | 2017-04-11 |
| AR091452A1 (es) | 2015-02-04 |
| CN104603135A (zh) | 2015-05-06 |
| CA2876015A1 (en) | 2013-12-27 |
| IN2014DN10069A (enExample) | 2015-08-14 |
| EP2861592A1 (en) | 2015-04-22 |
| EP2861592B1 (en) | 2016-04-06 |
| WO2013191988A1 (en) | 2013-12-27 |
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