CA2578185C - Utilisation de 2-mercapto-pyridine-n-oxyde - Google Patents

Utilisation de 2-mercapto-pyridine-n-oxyde Download PDF

Info

Publication number: CA2578185C
Authority: CA; Canada
Prior art keywords: oxide; pyridine; mercapto; parts; weight
Prior art date: 1997-06-13
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.): Expired - Fee Related

Application number

CA002578185A

Other languages

English (en)

Other versions

CA2578185A1 (fr

Inventor

Otto Exner

Heinz-Joachim Rother

Martin Kugler

Hartmut Rehbein

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1997-06-13

Filing date

1998-06-02

Publication date

2009-07-28

1997-06-13 Priority claimed from DE19725017A external-priority patent/DE19725017A1/de

1998-06-02 Application filed by Bayer AG filed Critical Bayer AG

1998-06-02 Priority to CA2661724A priority Critical patent/CA2661724C/fr

1998-12-17 Publication of CA2578185A1 publication Critical patent/CA2578185A1/fr

2009-07-28 Application granted granted Critical

2009-07-28 Publication of CA2578185C publication Critical patent/CA2578185C/fr

2018-06-02 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 title claims abstract description 18
-1 alkaline earth metal salts Chemical class 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
150000001340 alkali metals Chemical class 0.000 claims abstract description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 29
239000004480 active ingredient Substances 0.000 claims description 16
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 6
NCKMMSIFQUPKCK-UHFFFAOYSA-N 2-benzyl-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1CC1=CC=CC=C1 NCKMMSIFQUPKCK-UHFFFAOYSA-N 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 claims description 4
TUBQDCKAWGHZPF-UHFFFAOYSA-N 1,3-benzothiazol-2-ylsulfanylmethyl thiocyanate Chemical compound C1=CC=C2SC(SCSC#N)=NC2=C1 TUBQDCKAWGHZPF-UHFFFAOYSA-N 0.000 claims description 3
RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 claims description 3
HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 claims description 3
BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 claims description 3
IYOLBFFHPZOQGW-UHFFFAOYSA-N 2,4-dichloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=C(Cl)C(C)=C1Cl IYOLBFFHPZOQGW-UHFFFAOYSA-N 0.000 claims description 3
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 3
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 claims description 3
KFZXVMNBUMVKLN-UHFFFAOYSA-N 4-chloro-5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(Cl)=C(C)C=C1O KFZXVMNBUMVKLN-UHFFFAOYSA-N 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 claims description 3
XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 claims description 3
UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 claims description 3
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims description 3
150000004696 coordination complex Chemical class 0.000 claims description 3
229960003887 dichlorophen Drugs 0.000 claims description 3
ANUSOIHIIPAHJV-UHFFFAOYSA-N fenticlor Chemical compound OC1=CC=C(Cl)C=C1SC1=CC(Cl)=CC=C1O ANUSOIHIIPAHJV-UHFFFAOYSA-N 0.000 claims description 3
229950005344 fenticlor Drugs 0.000 claims description 3
JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 3
229960005323 phenoxyethanol Drugs 0.000 claims description 3
229960003500 triclosan Drugs 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 2
VOZSTWKINVCUQY-UHFFFAOYSA-N n-cyclohexyl-1,1-dioxo-1-benzothiophene-2-carboxamide Chemical compound C=1C2=CC=CC=C2S(=O)(=O)C=1C(=O)NC1CCCCC1 VOZSTWKINVCUQY-UHFFFAOYSA-N 0.000 claims description 2
239000010985 leather Substances 0.000 abstract description 12
241001465754 Metazoa Species 0.000 abstract description 11
229910052751 metal Chemical class 0.000 abstract description 5
239000002184 metal Chemical class 0.000 abstract description 5
238000004321 preservation Methods 0.000 abstract description 3
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 18
CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 12
229940070805 p-chloro-m-cresol Drugs 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
235000010292 orthophenyl phenol Nutrition 0.000 description 9
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 6
238000009472 formulation Methods 0.000 description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
235000013772 propylene glycol Nutrition 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241001123663 Penicillium expansum Species 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
241000221832 Amorphotheca resinae Species 0.000 description 2
241000228245 Aspergillus niger Species 0.000 description 2
241000374462 Aspergillus pseudoglaucus Species 0.000 description 2
241000235527 Rhizopus Species 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000000034 method Methods 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 1
241000079253 Byssochlamys spectabilis Species 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
241000222290 Cladosporium Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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 1
241000235395 Mucor Species 0.000 description 1
241001149951 Mucor mucedo Species 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
241000228153 Penicillium citrinum Species 0.000 description 1
240000005384 Rhizopus oryzae Species 0.000 description 1
235000013752 Rhizopus oryzae Nutrition 0.000 description 1
241000223261 Trichoderma viride Species 0.000 description 1
239000008272 agar Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
235000019568 aromas Nutrition 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
229940124561 microbicide Drugs 0.000 description 1
244000005700 microbiome Species 0.000 description 1
JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical class [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Landscapes

Pyridine Compounds (AREA)

CA002578185A 1997-06-13 1998-06-02 Utilisation de 2-mercapto-pyridine-n-oxyde Expired - Fee Related CA2578185C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA2661724A CA2661724C (fr)	1997-06-13	1998-06-02	Utilisation de 2-mercapto-pyridine-n-oxyde

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19725017.3		1997-06-13
DE19725017A DE19725017A1 (de)	1997-06-13	1997-06-13	Verwendung von 2-Mercapto-pyridin-N-oxid
CA002293555A CA2293555C (fr)	1997-06-13	1998-06-02	Utilisation de 2-mercapto-pyridine-n-oxyde

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002293555A Division CA2293555C (fr)	1997-06-13	1998-06-02	Utilisation de 2-mercapto-pyridine-n-oxyde

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2661724A Division CA2661724C (fr)	1997-06-13	1998-06-02	Utilisation de 2-mercapto-pyridine-n-oxyde

Publications (2)

Publication Number	Publication Date
CA2578185A1 CA2578185A1 (fr)	1998-12-17
CA2578185C true CA2578185C (fr)	2009-07-28

Family

ID=38051277

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002578185A Expired - Fee Related CA2578185C (fr)	1997-06-13	1998-06-02	Utilisation de 2-mercapto-pyridine-n-oxyde

Country Status (1)

Country	Link
CA (1)	CA2578185C (fr)

1998
- 1998-06-02 CA CA002578185A patent/CA2578185C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2578185A1 (fr)	1998-12-17

Legal Events

Date	Code	Title	Description
2007-02-27	EEER	Examination request
2015-07-14	MKLA	Lapsed	Effective date: 20150602

Publication	Publication Date	Title
CA2293555C (fr)	2007-05-15	Utilisation de 2-mercapto-pyridine-n-oxyde
AU690022B2 (en)	1998-04-09	Fungicidal composition
KR100841182B1 (ko)	2008-06-24	동물의 피부 및 가죽 보호용 활성 성분의 혼합물
AU763681B2 (en)	2003-07-31	Tanning leather
US6083414A (en)	2000-07-04	Composition of a mixture of a phenolic compound and an azole or morpholine compound to protect animal hides and leather against microbes
CA2578185C (fr)	2009-07-28	Utilisation de 2-mercapto-pyridine-n-oxyde
EP0410862B1 (fr)	1995-07-05	Procédé de traitement de peaux, et peaux obtenues
PL55625B1 (fr)	1968-06-25