JP5101826B2 - イソチアゾロン系化合物を含有する水溶性製剤およびイソチアゾロン系化合物の安定化方法 - Google Patents
イソチアゾロン系化合物を含有する水溶性製剤およびイソチアゾロン系化合物の安定化方法 Download PDFInfo
- Publication number
- JP5101826B2 JP5101826B2 JP2006052806A JP2006052806A JP5101826B2 JP 5101826 B2 JP5101826 B2 JP 5101826B2 JP 2006052806 A JP2006052806 A JP 2006052806A JP 2006052806 A JP2006052806 A JP 2006052806A JP 5101826 B2 JP5101826 B2 JP 5101826B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- isothiazolone compound
- alkali metal
- isothiazolone
- soluble preparation
- 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.)
- Active
Links
- -1 isothiazolone compound Chemical class 0.000 title claims description 89
- 238000002360 preparation method Methods 0.000 title claims description 69
- 238000000034 method Methods 0.000 title claims description 30
- 230000000087 stabilizing effect Effects 0.000 title description 7
- 239000007864 aqueous solution Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 229910052783 alkali metal Inorganic materials 0.000 claims description 22
- 229910001963 alkali metal nitrate Inorganic materials 0.000 claims description 20
- 150000007524 organic acids Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical group [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- BEGLCMHJXHIJLR-UHFFFAOYSA-N methylisothiazolinone Chemical compound CN1SC=CC1=O BEGLCMHJXHIJLR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000004317 sodium nitrate Substances 0.000 claims description 6
- 235000010344 sodium nitrate Nutrition 0.000 claims description 6
- 229940100555 2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 229940100484 5-chloro-2-methyl-4-isothiazolin-3-one Drugs 0.000 claims description 4
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 claims description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 4
- 230000006641 stabilisation Effects 0.000 claims description 4
- 238000011105 stabilization Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 2
- 239000004323 potassium nitrate Substances 0.000 claims description 2
- 235000010333 potassium nitrate Nutrition 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 238000003860 storage Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 230000035939 shock Effects 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 239000010730 cutting oil Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000008235 industrial water Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- MGIYRDNGCNKGJU-UHFFFAOYSA-N isothiazolinone Chemical class O=C1C=CSN1 MGIYRDNGCNKGJU-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- FMNZAHDAULEOSO-UHFFFAOYSA-N 2,2-dibromo-2-nitroethanol Chemical compound OCC(Br)(Br)[N+]([O-])=O FMNZAHDAULEOSO-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- NWPCFCBFUXXJIE-UHFFFAOYSA-N 2-(hydroxymethylamino)ethanol Chemical compound OCCNCO NWPCFCBFUXXJIE-UHFFFAOYSA-N 0.000 description 1
- HUHGPYXAVBJSJV-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyethyl)-1,3,5-triazinan-1-yl]ethanol Chemical compound OCCN1CN(CCO)CN(CCO)C1 HUHGPYXAVBJSJV-UHFFFAOYSA-N 0.000 description 1
- NCDBYAPSWOPDRN-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]sulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)F)C(=O)C2=C1 NCDBYAPSWOPDRN-UHFFFAOYSA-N 0.000 description 1
- NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 description 1
- KQGMHDNNHXMQST-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile;2,2-dibromo-2-cyanoacetamide Chemical compound NC(=O)C(Br)(Br)C#N.BrCC(Br)(C#N)CCC#N KQGMHDNNHXMQST-UHFFFAOYSA-N 0.000 description 1
- HHPJKICDWHTLAV-UHFFFAOYSA-N 2-cyclohexyl-1,2-thiazol-3-one Chemical compound O=C1C=CSN1C1CCCCC1 HHPJKICDWHTLAV-UHFFFAOYSA-N 0.000 description 1
- ASKFWACWQQZSSS-UHFFFAOYSA-N 2-ethyl-1,2-thiazol-3-one Chemical compound CCN1SC=CC1=O ASKFWACWQQZSSS-UHFFFAOYSA-N 0.000 description 1
- HFOCAQPWSXBFFN-UHFFFAOYSA-N 2-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=CC=C1C=O HFOCAQPWSXBFFN-UHFFFAOYSA-N 0.000 description 1
- 229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 description 1
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 1
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 1
- PORQOHRXAJJKGK-UHFFFAOYSA-N 4,5-dichloro-2-n-octyl-3(2H)-isothiazolone Chemical compound CCCCCCCCN1SC(Cl)=C(Cl)C1=O PORQOHRXAJJKGK-UHFFFAOYSA-N 0.000 description 1
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- NKEKPBPHPFSSIT-UHFFFAOYSA-N 5-chloro-2-(2,4,4-trimethylpentan-2-yl)-1,2-thiazol-3-one Chemical compound CC(C)(C)CC(C)(C)N1SC(Cl)=CC1=O NKEKPBPHPFSSIT-UHFFFAOYSA-N 0.000 description 1
- MMONDPHQMXRZDG-UHFFFAOYSA-N 5-chloro-2-ethyl-1,2-thiazol-3-one Chemical compound CCN1SC(Cl)=CC1=O MMONDPHQMXRZDG-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- WJLVQTJZDCGNJN-UHFFFAOYSA-N Chlorhexidine hydrochloride Chemical compound Cl.Cl.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WJLVQTJZDCGNJN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- 229920002413 Polyhexanide Polymers 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 1
- VZLZBGJVQPXXOI-UHFFFAOYSA-N [Cu].[O-][N+]1=CC=CC=C1S Chemical compound [Cu].[O-][N+]1=CC=CC=C1S VZLZBGJVQPXXOI-UHFFFAOYSA-N 0.000 description 1
- XDILZEPJCPEDLT-UHFFFAOYSA-N [Na].[O-][N+]1=CC=CC=C1S Chemical compound [Na].[O-][N+]1=CC=CC=C1S XDILZEPJCPEDLT-UHFFFAOYSA-N 0.000 description 1
- WPZSJJJTNREFSV-UHFFFAOYSA-N [Zn].[O-][N+]1=CC=CC=C1S Chemical compound [Zn].[O-][N+]1=CC=CC=C1S WPZSJJJTNREFSV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 1
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 229960001950 benzethonium chloride Drugs 0.000 description 1
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- OCBHHZMJRVXXQK-UHFFFAOYSA-M benzyl-dimethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 OCBHHZMJRVXXQK-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 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
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003333 chlorhexidine gluconate Drugs 0.000 description 1
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 1
- 229960004504 chlorhexidine hydrochloride Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- JJKSAEHNIHMQKQ-UHFFFAOYSA-N copper;quinoline Chemical compound [Cu].N1=CC=CC2=CC=CC=C21 JJKSAEHNIHMQKQ-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 229940078672 didecyldimethylammonium Drugs 0.000 description 1
- 229960004670 didecyldimethylammonium chloride Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000750 industrial fungicide Substances 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
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- APLYTANMTDCWTA-UHFFFAOYSA-L magnesium;phthalate Chemical compound [Mg+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O APLYTANMTDCWTA-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- FJQMEBQMRAFJPW-UHFFFAOYSA-N n-[dichloro(fluoro)methyl]sulfanyl-n-(dimethylsulfamoyl)-2-methylaniline Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1C FJQMEBQMRAFJPW-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 description 1
- 239000004331 potassium propionate Substances 0.000 description 1
- 235000010332 potassium propionate Nutrition 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 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
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 239000004753 textile Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- GAAKLDANOSASAM-UHFFFAOYSA-N undec-10-enoic acid;zinc Chemical compound [Zn].OC(=O)CCCCCCCCC=C GAAKLDANOSASAM-UHFFFAOYSA-N 0.000 description 1
- 229940118257 zinc undecylenate Drugs 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
(1)イソチアゾロン系化合物、アルカリ金属硝酸塩及び水を含有し、pHが3.5〜4.5の範囲内に調整されていることを特徴とするイソチアゾロン系化合物を含有する水溶性製剤。
(2)イソチアゾロン系化合物の含有量が、製剤全体に対して、1〜10重量%である(1)に記載のイソチアゾロン系化合物を含有する水溶性製剤。
(3)アルカリ金属硝酸塩の含有量が、製剤全体に対して、7重量%以上である(1)又は(2)に記載のイソチアゾロン系化合物を含有する水溶性製剤。
(5)イソチアゾロン系化合物が、5−クロロ−2−メチル−4−イソチアゾリン−3−オン、及び2−メチル−4−イソチアゾリン−3−オンの混合物である(4)に記載のイソチアゾロン系化合物を含有する水溶性製剤。
(7)有機酸のアルカリ金属塩をさらに含有する(1)〜(6)のいずれかに記載のイソチアゾロン系化合物を含有する水溶性製剤。
(8)有機酸のアルカリ金属塩が、酢酸のアルカリ金属塩である(7)に記載のイソチアゾロン系化合物を含有する水溶性製剤。
(9)イソチアゾロン系化合物、アルカリ金属硝酸塩、及び水を含有する水溶液に、有機酸のアルカリ金属塩を添加して、pHを3.5〜4.5の範囲内に調整することを特徴とするイソチアゾロン系化合物の安定化方法。
本発明の第2によれば、イソチアゾロン系化合物を水溶液中で、長期に亘って安定化することができるイソチアゾロン系化合物の安定化方法が提供される。
1)イソチアゾロン系化合物を含有する水溶性製剤
本発明のイソチアゾロン系化合物を含有する水溶性製剤は、イソチアゾロン系化合物、アルカリ金属硝酸塩及び水を含有し、pHが3.5〜4.5の範囲内に調整されていることを特徴とする。
本発明に用いるイソチアゾロン系化合物としては、イソチアゾロン骨格を有する殺菌活性を有する化合物であれば、特に制限されないが、下記式(1)
式(1)中、Yは、水素原子、又は置換されていてもよい炭化水素基を表す。
Yの置換されていてもよい炭化水素基の炭化水素基としては、炭素数1〜10のアルキル基、炭素数2〜6のアルケニル基、炭素数2〜6のアルキニル基、炭素数3〜10のシクロアルキル基、炭素数6〜14のアリール基等が挙げられる。
これらの中で、炭素数1〜10のアルキル基、炭素数3〜10のシクロアルキル基が好ましく、炭素数1〜10のアルキル基がより好ましい。
これらの中でも、X1、X2としては、X1、X2が共に水素原子である場合、X1、X2のうち、一方が水素原子で、他方がハロゲン原子である場合、X1、X2が共にハロゲン原子である場合のいずれかであるのが好ましい。また、ハロゲン原子としては、塩素原子が特に好ましい。
これらの中でも、5−クロロ−2−メチル−4−イソチアゾリン−3−オン、2−メチル−4−イソチアゾリン−3−オンが好ましい。
本発明の製剤は、アルカリ金属硝酸塩を含有する。アルカリ金属硝酸塩は、水溶液中のイソチアゾロン系化合物を安定化する機能を有する。また、硝酸マグネシウムなどのマグネシウム塩等をエマルション系塗料に大量に含有させると、エマルションショックを引き起こすことがあるが、本発明においては、アルカリ金属硝酸塩を使用するため、エマルション系塗料に大量に含有させ場合であっても、エマルションショックを引き起こすことがない。
本発明の水溶性製剤に用いる水としては、特に制約されず、水道水、蒸留水、脱イオン水等を使用することができる。より安定性に優れる水溶性製剤を得る上では、不純物の少ない蒸留水、脱イオン水等の使用が好ましい。
本発明の水溶性製剤は、pHが3.5〜4.5の範囲内、好ましくは3.7〜4.3の範囲内、より好ましくは3.9〜4.1の範囲内に調整されていることを特徴とする。pHをこのような範囲内に調整することにより、水溶液中において、長期に亘って安定した水溶性製剤を得ることができる。
有機酸のアルカリ金属塩としては、無機酸、カルボキシル基を有する有機化合物、スルホン酸、フェノール系化合物等が挙げられ、酢酸、トリフルオロ酢酸、フタル酸、クエン酸、ギ酸、シュウ酸、酒石酸等のカルボキシル基を有する有機化合物が好ましい。また、有機酸のアルカリ金属塩のアルカリ金属としては、リチウム、ナトリウム、カリウム、ルビジウム、セシウムが挙げられ、ナトリウム又はカリウムが好ましい。
また、保存安定性に影響を与えない範囲であれば、硝酸マグネシウム塩などのアルカリ土類金属塩、グリコール系有機溶媒等を少量含有していてもよい。
本発明のイソチアゾロン系化合物の安定化方法は、イソチアゾロン系化合物、アルカリ金属硝酸塩及び水を含有する水溶液に、有機酸のアルカリ金属塩を添加して、pHを3.5〜4.5の範囲内に調整することを特徴とする。本発明の安定化方法によれば、水溶液中において、長期に亘ってイソチアゾロン系化合物を安定して存在させることができる。
またその使用量も、使用の対象となる物や目的等により適宜定めることができる。
適当量のイオン交換水に、市販のイソチアゾロン系殺菌剤(商品名:KATHON WT、ローム&ハース社製、5−クロロ−2−メチル−4−イソチアゾリン−3−オンを約10重量%、2−メチル−4−イソチアゾリン−3−オンを約3重量%含有、以下、「殺菌剤A」と略記)及び硝酸ナトリウム(NaNO3)を第1表及び第2表に示す量添加して水溶液を得た。得られた水溶液に酢酸ナトリウムを少量加えて、所定のpHに調整した後、さらに、製剤全体が100重量部となるように少量のイオン交換水を添加して、実施例1〜8、比較例1〜4の水溶性製剤を調製した。実施例1〜8、比較例1〜4の水溶性製剤中の殺菌剤A及び硝酸ナトリウム(NaNO3)の含有量(重量部)、並びに、得られた各水溶性製剤のpHを第1表及び第2表にまとめて示す。
実施例1〜8、比較例1〜4で得た水溶性製剤の50mlをそれぞれサンプル瓶に入れ、密栓して室温で7日間放置した。その後、水溶性製剤の着色度を肉眼で観察した。着色が濃くなるほど、イソチアゾリン系化合物の分解が進んでいることを示す。
観察した結果、無色透明である場合を◎、ほとんど着色がない場合を○、うすく茶色に着色している場合を△、茶色に着色している場合を×で評価した。評価結果を第1表及び第2表に示す。
Claims (8)
- イソチアゾロン系化合物、アルカリ金属硝酸塩、有機酸のアルカリ金属塩及び水を含有し、pHが3.5〜4.5の範囲内に調整されていることを特徴とするイソチアゾロン系化合物を含有する水溶性製剤。
- イソチアゾロン系化合物の含有量が、製剤全体に対して、1〜10重量%である請求項1に記載のイソチアゾロン系化合物を含有する水溶性製剤。
- アルカリ金属硝酸塩の含有量が、製剤全体に対して、7重量%以上である請求項1又は2に記載のイソチアゾロン系化合物を含有する水溶性製剤。
- イソチアゾロン系化合物が、5−クロロ−2−メチル−4−イソチアゾリン−3−オン、及び2−メチル−4−イソチアゾリン−3−オンの混合物である請求項4に記載のイソチアゾロン系化合物を含有する水溶性製剤。
- アルカリ金属硝酸塩が、硝酸ナトリウム又は硝酸カリウムである請求項1〜5のいずれかに記載のイソチアゾロン系化合物を含有する水溶性製剤。
- 有機酸のアルカリ金属塩が、酢酸のアルカリ金属塩である請求項1〜6のいずれかに記載のイソチアゾロン系化合物を含有する水溶性製剤。
- イソチアゾロン系化合物、アルカリ金属硝酸塩及び水を含有する水溶液に、有機酸のアルカリ金属塩を添加して、pHを3.5〜4.5の範囲内に調整することを特徴とするイソチアゾロン系化合物の安定化方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006052806A JP5101826B2 (ja) | 2006-02-28 | 2006-02-28 | イソチアゾロン系化合物を含有する水溶性製剤およびイソチアゾロン系化合物の安定化方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006052806A JP5101826B2 (ja) | 2006-02-28 | 2006-02-28 | イソチアゾロン系化合物を含有する水溶性製剤およびイソチアゾロン系化合物の安定化方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007230892A JP2007230892A (ja) | 2007-09-13 |
JP5101826B2 true JP5101826B2 (ja) | 2012-12-19 |
Family
ID=38551854
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006052806A Active JP5101826B2 (ja) | 2006-02-28 | 2006-02-28 | イソチアゾロン系化合物を含有する水溶性製剤およびイソチアゾロン系化合物の安定化方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5101826B2 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013129739A (ja) * | 2011-12-21 | 2013-07-04 | Toagosei Co Ltd | 水性重合体エマルション組成物の製造方法 |
JP6925812B2 (ja) * | 2017-02-02 | 2021-08-25 | エステー株式会社 | 固形揮散製剤 |
JP7043366B2 (ja) * | 2018-08-08 | 2022-03-29 | エステー株式会社 | 固形揮散製剤 |
CN112400871A (zh) * | 2020-11-30 | 2021-02-26 | 洛阳市兽药厂 | 一种异噻唑啉酮类化合物可溶性粉及其制备工艺 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1189514A (en) * | 1982-06-01 | 1985-06-25 | Horst O. Bayer | Nitrosamine-free 3-isothiazolones and process |
US5478797A (en) * | 1994-11-21 | 1995-12-26 | Rohm And Haas Company | Bromate stabilization of nitrate-free 3-isothiazolones at pH 4-5.1 |
JPH09263504A (ja) * | 1995-12-19 | 1997-10-07 | Takeda Chem Ind Ltd | イソチアゾロン系化合物含有組成物及びイソチアゾロン系化合物の安定化法 |
KR100212963B1 (ko) * | 1995-12-21 | 1999-08-02 | 조민호 | 안정화된 이소티아졸론 조성물과 이소티아졸론 혼합물의 제조방법 |
JPH11171712A (ja) * | 1997-09-19 | 1999-06-29 | Ichikawa Gosei Kagaku Kk | イソチアゾロン製剤とその製造方法 |
US5910503A (en) * | 1997-10-28 | 1999-06-08 | Rohm And Haas Company | Stable microbicide formulation |
EP0983723A1 (en) * | 1998-08-31 | 2000-03-08 | Rohm And Haas Company | Stable microbicide formulation |
JP2002003307A (ja) * | 2000-06-23 | 2002-01-09 | Takeda Chem Ind Ltd | 工業用殺菌剤 |
EP1507771A4 (en) * | 2002-05-29 | 2006-08-30 | Sk Chemicals Co Ltd | ISOTHIAZOLON COMPOSITION AND METHOD FOR STABILIZING ISOTHIAZOLONE |
-
2006
- 2006-02-28 JP JP2006052806A patent/JP5101826B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
JP2007230892A (ja) | 2007-09-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4382175B2 (ja) | 安定な殺微生物剤配合物 | |
US5562995A (en) | Discoloration prevention in pyrithione-containing coating compositions | |
PT93633B (pt) | Processo para a preparacao de uma composicao biocidas contendo pelo menos um derivado de isotiazolinona ou de isotiazolotiona | |
JP5101826B2 (ja) | イソチアゾロン系化合物を含有する水溶性製剤およびイソチアゾロン系化合物の安定化方法 | |
HU202053B (en) | Stabilized isothiazolon compositions | |
US20210235699A1 (en) | Adjuvant Compositions Comprising a Tetramethylguanidine and a 4-Isothiazolin-3-One | |
ES2535610T3 (es) | Agentes biocidas | |
JP2005527626A (ja) | イソチアゾロン組成物及びイソチアゾロンの安定化方法 | |
WO2020246452A1 (ja) | 安定な殺微生物剤組成物 | |
KR0158368B1 (ko) | 안정화 3-이소티아졸론 조성물 및 그 용법 | |
JP2023541194A (ja) | 殺生物組成物及び方法 | |
CA2016384A1 (en) | Bismuth salt stabilizers for 3-isothiazolones | |
PT99867A (pt) | Processo para a preparacao de composicoes anti-microbianas contendo 4,5-polimetileno-4-isotiazolin-3-ona ou um seu derivado e um sal ou um complexo de 2-mercapto-piridina-1-oxido com um metal | |
WO2012033590A1 (en) | Chemically stable dispersions of prothioconazole and processes for preparing them | |
JP4567955B2 (ja) | 工業用抗菌組成物 | |
JPH09263504A (ja) | イソチアゾロン系化合物含有組成物及びイソチアゾロン系化合物の安定化法 | |
JPH05286815A (ja) | 工業用殺菌剤 | |
JP5340613B2 (ja) | 安定な殺菌防カビ組成物 | |
JP2005082596A (ja) | イソチアゾロン誘導体およびピリオンジスルフィドに基づく低塩含量または塩フリーの殺菌剤組成物 | |
JP2002003307A (ja) | 工業用殺菌剤 | |
JP3910672B2 (ja) | 安定化された工業用防カビ剤 | |
JP2834219B2 (ja) | 工業用殺菌・静菌組成物の安定化方法 | |
JPH10114605A (ja) | 安定化された工業用殺菌剤 | |
JP3576255B2 (ja) | イソチアゾロン系化合物含有組成物 | |
US20240237652A1 (en) | Biocidal Composition and Method |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20081219 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20111013 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111101 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20111221 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20111227 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120118 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120925 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120927 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151005 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5101826 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |