CA2010791C - Combinaisons microbicides synergiques contenant du 2-n-octyl-3-isothiazolone et certains biocides du commerce - Google Patents

Combinaisons microbicides synergiques contenant du 2-n-octyl-3-isothiazolone et certains biocides du commerce Download PDF

Info

Publication number: CA2010791C
Authority: CA; Canada
Prior art keywords: component; composition; range; ratio; hydroxymethyl
Prior art date: 1989-03-10
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 - Lifetime

Application number

CA 2010791

Other languages

English (en)

Other versions

CA2010791A1 (fr

Inventor

Jemin Charles Hsu

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas Co

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.)

1989-03-10

Filing date

1990-02-23

Publication date

2000-02-01

1989-03-10 Priority claimed from US07/322,455 external-priority patent/US4964892A/en

1990-02-23 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1990-09-10 Publication of CA2010791A1 publication Critical patent/CA2010791A1/fr

2000-02-01 Application granted granted Critical

2000-02-01 Publication of CA2010791C publication Critical patent/CA2010791C/fr

2010-02-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000002195 synergetic effect Effects 0.000 title claims abstract description 35
230000003641 microbiacidal effect Effects 0.000 title claims 2
239000003139 biocide Substances 0.000 title abstract description 11
JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 title abstract 2
239000000203 mixture Substances 0.000 claims abstract description 56
150000001875 compounds Chemical class 0.000 claims description 42
241000894006 Bacteria Species 0.000 claims description 33
241000233866 Fungi Species 0.000 claims description 30
238000000034 method Methods 0.000 claims description 22
-1 poly(methylenoxy Chemical group 0.000 claims description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
230000012010 growth Effects 0.000 claims description 12
241000195493 Cryptophyta Species 0.000 claims description 6
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 6
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 6
DBHODFSFBXJZNY-UHFFFAOYSA-N 2,4-dichlorobenzyl alcohol Chemical compound OCC1=CC=C(Cl)C=C1Cl DBHODFSFBXJZNY-UHFFFAOYSA-N 0.000 claims description 5
NWPCFCBFUXXJIE-UHFFFAOYSA-N 2-(hydroxymethylamino)ethanol Chemical compound OCCNCO NWPCFCBFUXXJIE-UHFFFAOYSA-N 0.000 claims description 5
DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 claims description 5
LHQKXYCMFLDMDH-UHFFFAOYSA-N 2-bromo-2-nitropropane-1,1-diol Chemical compound OC(O)C(Br)(C)[N+]([O-])=O LHQKXYCMFLDMDH-UHFFFAOYSA-N 0.000 claims description 5
JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 claims description 5
229960004698 dichlorobenzyl alcohol Drugs 0.000 claims description 5
ANUSOIHIIPAHJV-UHFFFAOYSA-N fenticlor Chemical compound OC1=CC=C(Cl)C=C1SC1=CC(Cl)=CC=C1O ANUSOIHIIPAHJV-UHFFFAOYSA-N 0.000 claims description 4
125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 4
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
238000011109 contamination Methods 0.000 claims description 3
JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 claims description 3
XYRTVIAPRQLSOW-UHFFFAOYSA-N 1,3,5-triethyl-1,3,5-triazinane Chemical compound CCN1CN(CC)CN(CC)C1 XYRTVIAPRQLSOW-UHFFFAOYSA-N 0.000 claims description 2
230000002411 adverse Effects 0.000 claims description 2
PASCYLAFGHJSHW-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)methyl]-3-(methylamino)propanoate Chemical compound CCOC(=O)C(CNC)CC1=CC=C(OC)C=C1 PASCYLAFGHJSHW-UHFFFAOYSA-N 0.000 claims description 2
POQVFNKHXUUDJR-UHFFFAOYSA-N 1-[[diiodo-(4-methylphenyl)methyl]sulfonyl-diiodomethyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(I)(I)S(=O)(=O)C(I)(I)C1=CC=C(C)C=C1 POQVFNKHXUUDJR-UHFFFAOYSA-N 0.000 claims 2
RGDPCZKNNXHAIU-UHFFFAOYSA-N 2-(hydroxymethylamino)-2-methylpropan-1-ol Chemical compound OCC(C)(C)NCO RGDPCZKNNXHAIU-UHFFFAOYSA-N 0.000 claims 2
229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 claims 2
WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 claims 2
OSDLLIBGSJNGJE-UHFFFAOYSA-N 4-chloro-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1Cl OSDLLIBGSJNGJE-UHFFFAOYSA-N 0.000 claims 2
239000012736 aqueous medium Substances 0.000 claims 1
WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 claims 1
229940044120 2-n-octyl-4-isothiazolin-3-one Drugs 0.000 abstract description 45
230000003115 biocidal effect Effects 0.000 abstract description 12
244000005700 microbiome Species 0.000 abstract description 8
230000000845 anti-microbial effect Effects 0.000 abstract description 3
206010041235 Snoring Diseases 0.000 abstract 1
238000012360 testing method Methods 0.000 description 71
239000002609 medium Substances 0.000 description 57
229940126062 Compound A Drugs 0.000 description 48
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 48
239000001974 tryptic soy broth Substances 0.000 description 39
108010050327 trypticase-soy broth Proteins 0.000 description 39
AVGVFDSUDIUXEU-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SCCC1=O AVGVFDSUDIUXEU-UHFFFAOYSA-N 0.000 description 28
230000000694 effects Effects 0.000 description 19
238000011156 evaluation Methods 0.000 description 16
241000588724 Escherichia coli Species 0.000 description 13
241000222122 Candida albicans Species 0.000 description 12
239000012530 fluid Substances 0.000 description 11
238000005555 metalworking Methods 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 5
MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 4
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 4
229960003887 dichlorophen Drugs 0.000 description 4
239000003973 paint Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011885 synergistic combination Substances 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
230000001580 bacterial effect Effects 0.000 description 3
238000000576 coating method Methods 0.000 description 3
230000002538 fungal effect Effects 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000013207 serial dilution Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000002023 wood Substances 0.000 description 2
JLHMJWHSBYZWJJ-UHFFFAOYSA-N 1,2-thiazole 1-oxide Chemical compound O=S1C=CC=N1 JLHMJWHSBYZWJJ-UHFFFAOYSA-N 0.000 description 1
CMNSJKWAGPRSRK-UHFFFAOYSA-N 2-octyl-3h-1,2-thiazole 1-oxide Chemical compound CCCCCCCCN1CC=CS1=O CMNSJKWAGPRSRK-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 1
YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241000132179 Eurotium medium Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229930006000 Sucrose Natural products 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
239000008272 agar Substances 0.000 description 1
230000005791 algae growth Effects 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
229960005091 chloramphenicol Drugs 0.000 description 1
239000004927 clay Substances 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000002173 cutting fluid Substances 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
239000000032 diagnostic agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000005553 drilling Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
238000004070 electrodeposition Methods 0.000 description 1
239000002979 fabric softener Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000011499 joint compound Substances 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
230000036407 pain Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000004391 petroleum recovery Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
238000007747 plating Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
229930187593 rose bengal Natural products 0.000 description 1
229940081623 rose bengal Drugs 0.000 description 1
STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
239000000565 sealant Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009182 swimming Effects 0.000 description 1
239000004753 textile Substances 0.000 description 1
229940055764 triaz Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA 2010791 1989-03-10 1990-02-23 Combinaisons microbicides synergiques contenant du 2-n-octyl-3-isothiazolone et certains biocides du commerce Expired - Lifetime CA2010791C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/322,455 US4964892A (en)	1988-12-22	1989-03-10	Synergistic microbicidal combinations containing 2-N-octyl-3-isothiazolone and certain commercial biocides
US322,455		1989-03-10

Publications (2)

Publication Number	Publication Date
CA2010791A1 CA2010791A1 (fr)	1990-09-10
CA2010791C true CA2010791C (fr)	2000-02-01

Family

ID=23254979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2010791 Expired - Lifetime CA2010791C (fr)	1989-03-10	1990-02-23	Combinaisons microbicides synergiques contenant du 2-n-octyl-3-isothiazolone et certains biocides du commerce

Country Status (1)

Country	Link
CA (1)	CA2010791C (fr)

1990
- 1990-02-23 CA CA 2010791 patent/CA2010791C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2010791A1 (fr)	1990-09-10

Legal Events

Date	Code	Title	Description
1997-02-17	EEER	Examination request
2010-02-23	MKEX	Expiry

Publication	Publication Date	Title
US4964892A (en)	1990-10-23	Synergistic microbicidal combinations containing 2-N-octyl-3-isothiazolone and certain commercial biocides
EP0608912B1 (fr)	1998-06-17	Combinaisons synergiques microbicides
EP0375264B1 (fr)	1995-01-25	Compositions biocides
US5468759A (en)	1995-11-21	Synergistic microbicidal combinations containing 4,5-dichloro-2-octyl-3-isothiazolone and certain commercial biocides
US5041457A (en)	1991-08-20	Synergistic microbicidal combinations containing 2-n-octyl-3-isothiazolone and certain commercial biocides
US5322834A (en)	1994-06-21	Synergistic microbicidal combinations containing 3-isothiazolin and commercial biocides
US4990525A (en)	1991-02-05	Synergistic microbicidal combinations containing 3-isothiazolone and commerical biocides
US5489588A (en)	1996-02-06	Synergistic microbicidal combinations containing 2-methyl-3-isothiazolone and certain commercial biocides
US5131939A (en)	1992-07-21	Synergistic microbicidal combinations containing 2-n-octyl-3-isothiazolone and certain commercial biocides
US5157045A (en)	1992-10-20	Biocidal combinations containing 4,5-dichloro-2-cyclohexyl-3-isothiazolone and certain commercial biocides
US5190944A (en)	1993-03-02	Synergistic microbicidal combinations containing 3-isothiazoline and commercial biocides
US5273987A (en)	1993-12-28	Biocidal combinations containing 4,5-dichloro-2-cyclohexyl-3-isothiazolone and certain commercial biocides
CA2010791C (fr)	2000-02-01	Combinaisons microbicides synergiques contenant du 2-n-octyl-3-isothiazolone et certains biocides du commerce
US5132306A (en)	1992-07-21	Synergistic microbicial combinations containing 3-isothiazolone and commercial biocides
US5294614A (en)	1994-03-15	Synergistic microbicidal composition comprising 3-isothiazolones and 1-methyl-3,5,7-triaza-1-azoniatricyclo(3.3.1.1)decane chloride
US5185355A (en)	1993-02-09	Biocidal combinations containing 4,5-dichloro-2-cyclohexyl-3-isothiazolone and certain commercial biocides