JP2015521619A - 抗微生物化合物 - Google Patents
抗微生物化合物 Download PDFInfo
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- JP2015521619A JP2015521619A JP2015518451A JP2015518451A JP2015521619A JP 2015521619 A JP2015521619 A JP 2015521619A JP 2015518451 A JP2015518451 A JP 2015518451A JP 2015518451 A JP2015518451 A JP 2015518451A JP 2015521619 A JP2015521619 A JP 2015521619A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 230000000845 anti-microbial effect Effects 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 244000005700 microbiome Species 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000012530 fluid Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- VARUTYJKNSICKT-UHFFFAOYSA-N 3-butyl-2-[3-(3-butyl-1,3-oxazolidin-2-yl)propyl]-1,3-oxazolidine Chemical compound CCCCN1CCOC1CCCC1OCCN1CCCC VARUTYJKNSICKT-UHFFFAOYSA-N 0.000 claims description 2
- DJYZXRFMKIBAOJ-UHFFFAOYSA-N 3-methyl-2-[3-(3-methyl-1,3-oxazolidin-2-yl)propyl]-1,3-oxazolidine Chemical compound CN1CCOC1CCCC1N(C)CCO1 DJYZXRFMKIBAOJ-UHFFFAOYSA-N 0.000 claims description 2
- JCIVIOSEFKULKF-UHFFFAOYSA-N 3-methyl-2-[3-(3-methyl-6-phenyl-1,3-oxazinan-2-yl)propyl]-6-phenyl-1,3-oxazinane Chemical compound CN1C(OC(CC1)C1=CC=CC=C1)CCCC1OC(CCN1C)C1=CC=CC=C1 JCIVIOSEFKULKF-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
- 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
- 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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000011248 coating agent Substances 0.000 claims 1
- 238000003754 machining Methods 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 abstract description 3
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 23
- 241000894006 Bacteria Species 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 230000000813 microbial effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241001148470 aerobic bacillus Species 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002953 phosphate buffered saline Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000001299 aldehydes Chemical class 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
- -1 secondary amine compound Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 2
- UVYBWDBLVDZIOX-UHFFFAOYSA-N 2-(octylamino)ethanol Chemical compound CCCCCCCCNCCO UVYBWDBLVDZIOX-UHFFFAOYSA-N 0.000 description 2
- XXSDCGNHLFVSET-UHFFFAOYSA-N 3-(methylamino)-1-phenylpropan-1-ol Chemical compound CNCCC(O)C1=CC=CC=C1 XXSDCGNHLFVSET-UHFFFAOYSA-N 0.000 description 2
- 241000203069 Archaea Species 0.000 description 2
- YJHPLDZMFZKYQZ-UHFFFAOYSA-N CCCCN1CCOC1CCCC=O Chemical compound CCCCN1CCOC1CCCC=O YJHPLDZMFZKYQZ-UHFFFAOYSA-N 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
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 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
- 238000004458 analytical method Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- 229940126214 compound 3 Drugs 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
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000011521 glass Substances 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
- 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
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 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
- 125000001624 naphthyl group Chemical group 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
- 239000012044 organic layer Substances 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
- 239000000843 powder Substances 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
- 150000003335 secondary amines Chemical class 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Paper (AREA)
- Detergent Compositions (AREA)
Abstract
Description
R1は直鎖状または分枝状C1−C10アルキルであり;
R2はH、直鎖状もしくは分枝状C1−C10アルキル、C3−C8シクロアルキルまたはアリールであり;
R3、R4およびR5は、各存在において互いに独立してH、直鎖状もしくは分枝状C1−C10アルキルまたはC3−C8シクロアルキルであり;
またはR2およびR3は、これらが結合している炭素と共にC3−C8シクロアルキルを形成し;
またはR4およびR5は、これらが結合している炭素と共にC3−C8シクロアルキルを形成し;ならびに
XはOまたはNR6であり、ここでR6は直鎖状または分枝状C1−C6アルキルである)の化合物を提供する。
R1は直鎖状または分枝状C1−C10アルキルであり;
R2はH、直鎖状もしくは分枝状C1−C10アルキル、C3−C8シクロアルキルまたはアリールであり;
R3、R4およびR5は、各存在において互いに独立してH、直鎖状もしくは分枝状C1−C10アルキルまたはC3−C8シクロアルキルであり;
またはR2およびR3は、これらが結合している炭素と共にC3−C8シクロアルキルを形成し;
またはR4およびR5は、これらが結合している炭素と共にC3−C8シクロアルキルを形成し;ならびに
XはOまたはNR6であり、ここでR6は直鎖状または分枝状C1−C6アルキルである)によって表すことができる。
殺菌効力についてのアッセイ
室温での殺菌効力についてのアッセイ:グルタルアルデヒドおよび化合物1と化合物4は、室温での好気性菌のプールに対して、および室温での硫酸塩還元菌(SRB)に対して殺菌活性を試験する。以下の通りに試験を行う:
a.原液の調製:グルタルアルデヒド(水中溶解50%)と化合物1と化合物4とを各々DMSOで200mMの濃度まで溶解する。これは20,000ppmの遊離グルタルアルデヒドに相当する。
b. 好気性菌−リン酸緩衝生理食塩水中の約5×106CFU/mLの6種類の菌種の混合プールを96ウェルプレートに分配する。各ウェルには、試験した化合物の独立した化学的処理をグルタルアルデヒドが200ppmから12ppmまでの濃度で施す。DMSO単独の対照処理も含まれる。各状態は、三つ組で試験する。設定期間(1、4および24時間)でのインキュベーション後、各ウェル中の生存細胞の数は、指標としてレサズリン色素を含有する培地中で希釈から消滅によって数え上げる。
c.硫酸塩還元菌(SRB)−SRB試験は、好気性菌に関して以下の改変で行う:デスルホビブリオ・ロンガス種(Desulfovibrio longus)を嫌気性PBS中で試験して、指標として溶解性鉄を含有する培地中で生存細胞の数え上げを行う。
d.結果:値は、細菌レベルにおいて3−log減少を達成するために必要な最小量(ppmで)を示す。「n/a」は、閾値が試験した用量のいずれでも適合しないことを示す。「N.D.」は、利用可能なデータがないことを示す。
保存液のグルタルアルデヒド当量濃度が20,000ppmになるように、化合物1をDMSOに溶解して200mM溶液を得る。菌種サーマス・サーモフィラス(Thermus thermophilus)(ATCC27634)は、70℃で維持する。24〜48時間の増殖の後、10mLの細菌培養をBeckman−Coulter卓上型遠心機中で3000rpmで15分間回転させることによって収集する。細胞ペレットを100mLのリン酸緩衝生理食塩水(PBS)で再懸濁して、約5×105CFU/mLを得て、ねじ口が付いたガラス試験管に10mL部に等分する。試料を30分間、37℃、55℃または70℃に平衡化し、次いで50ppmのグルタルアルデヒド同等物でグルタルアルデヒドまたは化合物1で処理する。処理した試料は、4時間の間それぞれの平衡温度まで戻し、次いで生存細菌を数え上げる。24時間後、再度殺菌を行うために新鮮な増殖細菌を試料に加えてこのプロセスを繰り返す。4時間後、再度試料を数え上げる。
Claims (9)
- 式I:
R1は直鎖状または分枝状C1−C10アルキルであり;
R2はH、直鎖状もしくは分枝状C1−C10アルキル、C3−C8シクロアルキル、またはアリールであり;
R3、R4およびR5は、各存在において互いに独立してH、直鎖状もしくは分枝状C1−C10アルキルまたはC3−C8シクロアルキルであり;
またはR2およびR3は、これらが結合している炭素と共にC3−C8シクロアルキルを形成し;
またはR4およびR5は、これらが結合している炭素と共にC3−C8シクロアルキルを形成し;ならびに
XはOまたはNR6であり、ここでR6は直鎖状または分枝状C1−C6アルキルである)の化合物。 - nが1であり、R2がアリールであり、ならびにR3、R4およびR5が各Hである、請求項1に記載の化合物。
- nが0であり、ならびにR2、R3、R4およびR5が各Hである、請求項1に記載の化合物。
- XがOである、請求項1〜3のいずれか1項に記載の化合物。
- 前記化合物が、1,3−ビス(3−メチルオキサゾリジン−2−イル)プロパン;1,3−ビス(3−ブチルオキサゾリジン−2−イル)プロパン;1,3−ビス(3−オクチルオキサゾリジン−2−イル)プロパン;または1,3−ビス(3−メチル−6−フェニル−1,3−オキサジナン−2−イル)プロパンである、請求項1に記載の化合物。
- 水性システムもしくは水含有システム中または水分に曝されているシステム中の微生物を抑制する方法であって、前記方法が前記システムを請求項1〜5のいずれか1項に記載の前記化合物と接触させることを含む、方法。
- 前記システムが少なくとも40℃の温度である、請求項6に記載の方法。
- 前記システムが油田もしくはガス田流体、製紙機械白水、産業再循環水、デンプン溶液、ラテックスもしくはポリマーエマルジョン、高温で製造されるコーティング材もしくは建材もしくは家庭用品もしくはパーソナルケア製品、プラスチック、熱間圧延機械加工液、工業用食器洗浄機用液もしくはクリーニング用液、アニマルバイオセキュリティー溶液、または高レベルの消毒液である、請求項6〜7のいずれか1項に記載の方法。
- 前記システムがフラクチャリング流体、掘削流体、水功法システム、油田水または生産流体である、請求項6〜8のいずれか1項に記載の方法。
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PCT/US2013/045408 WO2013191986A1 (en) | 2012-06-19 | 2013-06-12 | Antimicrobial compounds |
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JPH02231482A (ja) * | 1988-12-05 | 1990-09-13 | Ecolab Inc | 抗菌性フイルム形成組成物 |
US5334615A (en) * | 1992-12-17 | 1994-08-02 | Walles Wilhelm E | Oil with bactericidal and virucidal properties |
JP2002542380A (ja) * | 1999-04-20 | 2002-12-10 | ザ、プロクター、エンド、ギャンブル、カンパニー | 芳香剤原料アルデヒドおよび第三級α炭素原子をもつ芳香剤原料前駆体 |
WO2007079869A2 (de) * | 2005-12-23 | 2007-07-19 | Henkel Kommanditgesellschaft Auf Aktien | Cyclische aminale als duftstoffe |
WO2010108324A1 (en) * | 2009-03-26 | 2010-09-30 | Dow Global Technologies Inc. | Biocidal composition of 2,6-dimethyl-m-dioxane-4-ol acetate and methods of use |
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RU2014153680A (ru) | 2016-08-10 |
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CN104619688A (zh) | 2015-05-13 |
AU2013277509B2 (en) | 2017-11-16 |
CN104619688B (zh) | 2017-07-18 |
US9550740B2 (en) | 2017-01-24 |
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AU2013277509A1 (en) | 2015-01-15 |
JP6250655B2 (ja) | 2017-12-20 |
CA2876014A1 (en) | 2013-12-27 |
WO2013191986A1 (en) | 2013-12-27 |
AR091453A1 (es) | 2015-02-04 |
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