MX2014013991A - Compuestos biocidas y metodos para usar los mismos. - Google Patents
Compuestos biocidas y metodos para usar los mismos.Info
- Publication number
- MX2014013991A MX2014013991A MX2014013991A MX2014013991A MX2014013991A MX 2014013991 A MX2014013991 A MX 2014013991A MX 2014013991 A MX2014013991 A MX 2014013991A MX 2014013991 A MX2014013991 A MX 2014013991A MX 2014013991 A MX2014013991 A MX 2014013991A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- independently
- halamin
- alkoxy
- taken together
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 240
- 230000003115 biocidal effect Effects 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title description 30
- 239000002243 precursor Substances 0.000 claims abstract description 116
- 239000000758 substrate Substances 0.000 claims abstract description 54
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 13
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 7
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 24
- 238000005658 halogenation reaction Methods 0.000 claims description 24
- -1 non-aromatic ring cyclic ether Chemical class 0.000 claims description 24
- 230000026030 halogenation Effects 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000645 desinfectant Substances 0.000 claims description 8
- 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 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- APJAEXGNDLFGPD-AWCRTANDSA-N 3-amino-n-{4-[2-(2,6-dimethyl-phenoxy)-acetylamino]-3-hydroxy-1-isobutyl-5-phenyl-pentyl}-benzamide Chemical compound C([C@@H]([C@@H](O)C[C@H](CC(C)C)NC(=O)C=1C=CC(N)=CC=1)NC(=O)COC=1C(=CC=CC=1C)C)C1=CC=CC=C1 APJAEXGNDLFGPD-AWCRTANDSA-N 0.000 claims description 3
- ZOUTYVWHWSUKPL-NOZJJQNGSA-N C[C@H](CS)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(O)=O Chemical compound C[C@H](CS)C(=O)N[C@H](Cc1c[nH]c2ccccc12)C(O)=O ZOUTYVWHWSUKPL-NOZJJQNGSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- PTUCPHGSAFOJAU-MGONOCMRSA-N (4s)-5-amino-4-[[(2s)-2-[[(2s)-2-[[(4-bromophenyl)-hydroxyphosphoryl]methyl]-3-[3-[4-(3-chlorophenyl)phenyl]-1,2-oxazol-5-yl]propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N)CP(O)(=O)C=1C=CC(Br)=CC=1)C(ON=1)=CC=1C(C=C1)=CC=C1C1=CC=CC(Cl)=C1 PTUCPHGSAFOJAU-MGONOCMRSA-N 0.000 claims 2
- ZHDHSBKTLRLUCQ-UHFFFAOYSA-N 6-[4-(6-bromo-1,2-benzothiazol-3-yl)phenoxy]-n-methyl-n-prop-2-enylhexan-1-amine Chemical compound C1=CC(OCCCCCCN(C)CC=C)=CC=C1C1=NSC2=CC(Br)=CC=C12 ZHDHSBKTLRLUCQ-UHFFFAOYSA-N 0.000 claims 2
- 101100350474 Oryza sativa subsp. japonica RR41 gene Proteins 0.000 claims 1
- 101100350475 Oryza sativa subsp. japonica RR42 gene Proteins 0.000 claims 1
- 150000003997 cyclic ketones Chemical class 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 abstract description 57
- 239000000126 substance Substances 0.000 abstract description 9
- 239000000463 material Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 6
- 239000000654 additive Substances 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 3
- 244000000010 microbial pathogen Species 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 description 87
- 239000000243 solution Substances 0.000 description 80
- 229920000742 Cotton Polymers 0.000 description 79
- 229910052801 chlorine Inorganic materials 0.000 description 65
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 64
- 230000000844 anti-bacterial effect Effects 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 50
- 230000001580 bacterial effect Effects 0.000 description 50
- 230000009467 reduction Effects 0.000 description 46
- 239000004744 fabric Substances 0.000 description 44
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 33
- 241000894006 Bacteria Species 0.000 description 32
- 238000005660 chlorination reaction Methods 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000005481 NMR spectroscopy Methods 0.000 description 31
- 206010041925 Staphylococcal infections Diseases 0.000 description 31
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 31
- 230000008030 elimination Effects 0.000 description 30
- 238000003379 elimination reaction Methods 0.000 description 30
- 229910052736 halogen Inorganic materials 0.000 description 30
- 229920000139 polyethylene terephthalate Polymers 0.000 description 30
- 239000005020 polyethylene terephthalate Substances 0.000 description 30
- 229910001868 water Inorganic materials 0.000 description 30
- 239000000725 suspension Substances 0.000 description 27
- 150000002367 halogens Chemical class 0.000 description 26
- 239000007787 solid Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 22
- 125000000304 alkynyl group Chemical group 0.000 description 20
- 239000003139 biocide Substances 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- 150000001408 amides Chemical class 0.000 description 15
- 241000588724 Escherichia coli Species 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 12
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 12
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 11
- 150000001768 cations Chemical class 0.000 description 11
- 230000007246 mechanism Effects 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000006870 function Effects 0.000 description 10
- 244000005700 microbiome Species 0.000 description 10
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 10
- 230000002195 synergetic effect Effects 0.000 description 10
- 229920001817 Agar Polymers 0.000 description 9
- 239000008272 agar Substances 0.000 description 9
- 239000002953 phosphate buffered saline Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000002054 inoculum Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229920001429 chelating resin Polymers 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003957 anion exchange resin Substances 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 230000036541 health Effects 0.000 description 6
- 230000002779 inactivation Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 6
- 235000019345 sodium thiosulphate Nutrition 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 229940126543 compound 14 Drugs 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000005102 attenuated total reflection Methods 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000012650 click reaction Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 150000001469 hydantoins Chemical class 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 4
- 239000006916 nutrient agar Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126142 compound 16 Drugs 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 3
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- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 3
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- 238000001228 spectrum Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 229920000271 Kevlar® Polymers 0.000 description 2
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- 239000004677 Nylon Substances 0.000 description 2
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
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- 150000003868 ammonium compounds Chemical class 0.000 description 2
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- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical group O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical class C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- GSDQVZMTWWSMNU-UHFFFAOYSA-N 1-chloroimidazolidine-2,4-dione Chemical compound ClN1CC(=O)NC1=O GSDQVZMTWWSMNU-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CSTIZSQKHUSKHU-UHFFFAOYSA-N 2-azidoethanamine Chemical compound NCCN=[N+]=[N-] CSTIZSQKHUSKHU-UHFFFAOYSA-N 0.000 description 1
- KAWXOFVNMTULCZ-UHFFFAOYSA-N 2-azidoethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCN=[N+]=[N-] KAWXOFVNMTULCZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
- C07D233/82—Halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
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- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261648167P | 2012-05-17 | 2012-05-17 | |
| US201361772440P | 2013-03-04 | 2013-03-04 | |
| PCT/CA2013/000491 WO2013173905A1 (en) | 2012-05-17 | 2013-05-16 | Biocidal compounds and methods for using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2014013991A true MX2014013991A (es) | 2015-08-06 |
Family
ID=49622958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2014013991A MX2014013991A (es) | 2012-05-17 | 2013-05-16 | Compuestos biocidas y metodos para usar los mismos. |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US20150118179A1 (https=) |
| EP (2) | EP3357920A1 (https=) |
| JP (2) | JP2015523331A (https=) |
| CN (1) | CN104968655A (https=) |
| AU (1) | AU2013265971A1 (https=) |
| CA (1) | CA2869634C (https=) |
| IN (1) | IN2014DN09443A (https=) |
| MX (1) | MX2014013991A (https=) |
| WO (1) | WO2013173905A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2880639A1 (en) * | 2012-08-01 | 2014-02-06 | The Hospital For Sick Children | Inhibitors of peptidyl arginine deiminase (pad) enzymes and uses thereof |
| CN104910208B (zh) * | 2015-05-15 | 2017-07-21 | 大连理工大学 | 季膦盐型卤胺抗菌剂及其制备方法 |
| CN104926787A (zh) * | 2015-05-15 | 2015-09-23 | 大连理工大学 | 吡啶季铵盐型卤胺抗菌剂及其制备方法 |
| CA3001921C (en) | 2015-10-16 | 2021-04-27 | Exigence Technologies Inc. | Compounds, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group |
| WO2017079825A1 (en) * | 2015-11-13 | 2017-05-18 | Exigence Technologies Inc. | Monomers, polymers and coating formulations that comprise at least one n-halamine precursor, a cationic center and a coating incorporation group |
| CN105613506B (zh) * | 2016-03-22 | 2018-06-19 | 江南大学 | 一种卤胺/季铵烯烃类抗菌剂及其在生物可降解纳米纤维材料中的应用 |
| WO2017197518A1 (en) * | 2016-05-18 | 2017-11-23 | Exigence Technologies Inc. | Compounds with one or more functional groups and use thereof in liquid disinfectants |
| US10882822B2 (en) | 2016-07-06 | 2021-01-05 | University Of Manitoba | Use of compounds for making products with at least one N-halamine precursor group and at least one cationic center |
| CN106359383A (zh) * | 2016-08-08 | 2017-02-01 | 山东科技大学 | 一种含双键、季铵盐和卤胺双官能杀菌剂及其制备方法和应用 |
| US20190364895A1 (en) * | 2016-09-13 | 2019-12-05 | Exigence Technologies Inc. | Antimicrobial compounds or precursors thereof comrpising one or more cationic centers and a coating-incorporation group |
| CN107778248B (zh) * | 2017-11-17 | 2019-08-20 | 大连理工大学 | 双季铵盐型氯胺抗菌剂及其的合成方法 |
| US10611986B1 (en) | 2018-03-15 | 2020-04-07 | Earthcare Labs, Llc | Cleaning composition comprising a cationic/nonionic mixture |
| CN108378039B (zh) * | 2018-04-18 | 2020-08-25 | 大连理工大学 | 甜菜碱型氯胺抗菌剂及其合成方法 |
| WO2019200478A1 (en) * | 2018-04-20 | 2019-10-24 | Exigence Technologies Inc. | Use of compounds for making products with at least one n-halamine precursor group and at least one cationic center |
| CN108752279A (zh) * | 2018-07-18 | 2018-11-06 | 大连理工大学 | 一种锍盐型氯胺抗菌剂及其合成方法 |
| CN110372533B (zh) * | 2019-07-20 | 2021-06-15 | 大连理工大学 | 一种阳离子型线性氯胺抗菌剂及其合成方法 |
| CN116041266B (zh) * | 2022-12-30 | 2025-07-15 | 浙江大学绍兴研究院 | 一种序列可编码聚离子液体的合成方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787619A (en) * | 1955-04-08 | 1957-04-02 | Rohm & Haas | Method of producing nu-vinyl-nu, nu'-ethyleneurea |
| US2840546A (en) * | 1956-01-06 | 1958-06-24 | Rohm & Haas | Unsaturated quaternary ammonium compounds and polymers |
| US4073924A (en) * | 1976-10-04 | 1978-02-14 | Glyco Chemicals, Inc. | Hydantoin derivatives and broad spectrum bactericidal/fungicidal compositions thereof |
| DE2744353A1 (de) * | 1976-10-04 | 1978-04-13 | Glyco Chemicals Inc | Hydantoinderivate, verfahren zu ihrer herstellung und ihre verwendung |
| US4073926A (en) * | 1976-10-04 | 1978-02-14 | Glyco Chemicals, Inc. | Mono-quaternary ammonium salts of hydantoin and compositions thereof |
| US4820437A (en) * | 1986-09-18 | 1989-04-11 | Lion Corporation | Bleaching composition |
| US5882357A (en) * | 1996-09-13 | 1999-03-16 | The Regents Of The University Of California | Durable and regenerable microbiocidal textiles |
| US6768009B1 (en) * | 2000-03-24 | 2004-07-27 | The Regents Of The University Of California | N-halamine vinyl compounds and their polymeric biocides |
| US6969769B2 (en) * | 2002-06-14 | 2005-11-29 | Vanson Halosource, Inc. | N-halamine siloxanes for use in biocidal coatings and materials |
| US7687072B2 (en) * | 2002-10-31 | 2010-03-30 | Auburn University | Biocidal particles of methylated polystyrene |
| MX2007008152A (es) * | 2005-01-03 | 2007-09-12 | Univ Texas | Metodo para la transformacion de polimeros convencionales y comercialmente importantes en materiales polimericos antimicrobianos durables y recargables. |
| CA2618732A1 (en) * | 2005-08-11 | 2007-10-25 | Auburn University | N-halamine/quaternary ammonium polysiloxane copolymers |
| WO2008156636A1 (en) * | 2007-06-12 | 2008-12-24 | Michigan Molecular Institute | Antimicrobial coatings for conversion of spores into their bacterial vegetative form for decontamination |
| JP2011501732A (ja) * | 2007-09-19 | 2011-01-13 | ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム | 着色剤ベースのｎ−ハラミン組成物並びに製造及び使用の方法 |
| JP5599808B2 (ja) * | 2008-11-07 | 2014-10-01 | ノバベイ・ファーマシューティカルズ・インコーポレイテッド | 抗菌性ｎ−塩素化組成物 |
| WO2010054009A1 (en) * | 2008-11-07 | 2010-05-14 | Novabay Pharmaceuticals, Inc. | Antimicrobial oxazolidinone, hydantoin and imidazolidinone compositions |
| AU2011317223A1 (en) * | 2010-10-19 | 2013-05-23 | Novabay Pharmaceuticals, Inc. | Antimicrobial polyether and polyol compounds |
-
2013
- 2013-05-16 AU AU2013265971A patent/AU2013265971A1/en not_active Abandoned
- 2013-05-16 EP EP17196453.9A patent/EP3357920A1/en not_active Withdrawn
- 2013-05-16 EP EP13793373.5A patent/EP2850077A4/en not_active Withdrawn
- 2013-05-16 US US14/398,926 patent/US20150118179A1/en not_active Abandoned
- 2013-05-16 CA CA2869634A patent/CA2869634C/en active Active
- 2013-05-16 MX MX2014013991A patent/MX2014013991A/es unknown
- 2013-05-16 JP JP2015511872A patent/JP2015523331A/ja active Pending
- 2013-05-16 WO PCT/CA2013/000491 patent/WO2013173905A1/en not_active Ceased
- 2013-05-16 CN CN201380037584.3A patent/CN104968655A/zh active Pending
-
2014
- 2014-11-10 IN IN9443DEN2014 patent/IN2014DN09443A/en unknown
-
2017
- 2017-03-09 US US15/454,331 patent/US20170204085A1/en not_active Abandoned
- 2017-04-18 JP JP2017082342A patent/JP2017178947A/ja active Pending
- 2017-10-30 US US15/798,131 patent/US20180086740A1/en not_active Abandoned
-
2019
- 2019-02-01 US US16/265,607 patent/US20190233401A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20170204085A1 (en) | 2017-07-20 |
| CN104968655A (zh) | 2015-10-07 |
| CA2869634C (en) | 2018-11-27 |
| EP3357920A1 (en) | 2018-08-08 |
| US20180086740A1 (en) | 2018-03-29 |
| JP2017178947A (ja) | 2017-10-05 |
| JP2015523331A (ja) | 2015-08-13 |
| EP2850077A1 (en) | 2015-03-25 |
| EP2850077A4 (en) | 2015-08-26 |
| WO2013173905A1 (en) | 2013-11-28 |
| CA2869634A1 (en) | 2013-11-28 |
| AU2013265971A1 (en) | 2014-12-18 |
| US20190233401A1 (en) | 2019-08-01 |
| IN2014DN09443A (https=) | 2015-07-17 |
| US20150118179A1 (en) | 2015-04-30 |
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