FR2460623A1 - Composition microbicide/microbiostatique a base de 4,5-dichloro-1,2-dithiol-3-one et procede de destruction et/ou d'inhibition des microbes - Google Patents
Composition microbicide/microbiostatique a base de 4,5-dichloro-1,2-dithiol-3-one et procede de destruction et/ou d'inhibition des microbes Download PDFInfo
- Publication number
- FR2460623A1 FR2460623A1 FR8014738A FR8014738A FR2460623A1 FR 2460623 A1 FR2460623 A1 FR 2460623A1 FR 8014738 A FR8014738 A FR 8014738A FR 8014738 A FR8014738 A FR 8014738A FR 2460623 A1 FR2460623 A1 FR 2460623A1
- Authority
- FR
- France
- Prior art keywords
- dithiol
- dichloro
- acid ester
- bis
- haloacetic acid
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- QGSRKGWCQSATCL-UHFFFAOYSA-N 4,5-dichloro-3h-1,3-dithiol-2-one Chemical compound ClC=1SSC(=O)C=1Cl QGSRKGWCQSATCL-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 15
- 230000003158 microbiostatic effect Effects 0.000 title claims description 13
- 230000005764 inhibitory process Effects 0.000 title description 2
- 230000006378 damage Effects 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 40
- 230000008569 process Effects 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- 150000002148 esters Chemical class 0.000 claims description 47
- -1 2- (2-chloroethoxy) ethyl Chemical group 0.000 claims description 28
- 239000010802 sludge Substances 0.000 claims description 24
- 239000004615 ingredient Substances 0.000 claims description 20
- 230000003641 microbiacidal effect Effects 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 14
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000000295 fuel oil Substances 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- SIHKVAXULDBIIY-UPHRSURJSA-N [(z)-4-(2-bromoacetyl)oxybut-2-enyl] 2-bromoacetate Chemical compound BrCC(=O)OC\C=C/COC(=O)CBr SIHKVAXULDBIIY-UPHRSURJSA-N 0.000 claims description 5
- NNPJKFMGVZNJHG-UHFFFAOYSA-N hexyl 2-bromoacetate Chemical group CCCCCCOC(=O)CBr NNPJKFMGVZNJHG-UHFFFAOYSA-N 0.000 claims description 5
- RXRRMKNUVQKPIQ-UHFFFAOYSA-N 2-butoxyethyl 2-chloroacetate Chemical compound CCCCOCCOC(=O)CCl RXRRMKNUVQKPIQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 claims description 4
- 239000000498 cooling water Substances 0.000 claims description 4
- 239000010730 cutting oil Substances 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- HIIBHBNRMVLLKH-UHFFFAOYSA-N 2-(2-chloroacetyl)oxyethyl 2-chloroacetate Chemical compound ClCC(=O)OCCOC(=O)CCl HIIBHBNRMVLLKH-UHFFFAOYSA-N 0.000 claims description 3
- INYAPRIMIHLNCT-UHFFFAOYSA-N 6-(2-bromoacetyl)oxyhex-3-ynyl 2-bromoacetate Chemical compound BrCC(=O)OCCC#CCCOC(=O)CBr INYAPRIMIHLNCT-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 230000003373 anti-fouling effect Effects 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- QIPFGFYXERNTNP-UHFFFAOYSA-N dodecyl 2-bromoacetate Chemical compound CCCCCCCCCCCCOC(=O)CBr QIPFGFYXERNTNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229920005610 lignin Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- XMSIJJBCVVVNPG-UHFFFAOYSA-N (3-bromo-2-nitrobutyl) 2-bromoacetate Chemical compound CC(Br)C([N+]([O-])=O)COC(=O)CBr XMSIJJBCVVVNPG-UHFFFAOYSA-N 0.000 claims description 2
- GPIWNUTUJAZAMZ-UHFFFAOYSA-N 1,1-bis[(2-bromoacetyl)oxy]propyl 2-bromoacetate Chemical compound BrCC(=O)OC(CC)(OC(CBr)=O)OC(CBr)=O GPIWNUTUJAZAMZ-UHFFFAOYSA-N 0.000 claims description 2
- KBCCFFGCRDUANG-UHFFFAOYSA-N 2-(2-iodoacetyl)oxyethyl 2-iodoacetate Chemical compound ICC(=O)OCCOC(=O)CI KBCCFFGCRDUANG-UHFFFAOYSA-N 0.000 claims description 2
- OPGXPDPPQCMKEC-UHFFFAOYSA-N 2-phenoxyethyl 2-bromoacetate Chemical compound BrCC(=O)OCCOC1=CC=CC=C1 OPGXPDPPQCMKEC-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 claims description 2
- 229920000126 latex Polymers 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- UOWASDPNEZOQNB-UHFFFAOYSA-N 4-(2-chloroacetyl)oxybut-2-enyl 2-chloroacetate Chemical compound ClCC(=O)OCC=CCOC(=O)CCl UOWASDPNEZOQNB-UHFFFAOYSA-N 0.000 claims 2
- CJUOWAWICLNGCQ-UHFFFAOYSA-N 2,3-bis[(2-bromoacetyl)oxy]propyl 2-bromoacetate Chemical group BrCC(=O)OCC(OC(=O)CBr)COC(=O)CBr CJUOWAWICLNGCQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 239000010842 industrial wastewater Substances 0.000 claims 1
- 239000004816 latex Substances 0.000 claims 1
- 230000035755 proliferation Effects 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 description 39
- 241000894006 Bacteria Species 0.000 description 35
- 238000012360 testing method Methods 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 238000007792 addition Methods 0.000 description 31
- 239000003795 chemical substances by application Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000004480 active ingredient Substances 0.000 description 19
- 230000000694 effects Effects 0.000 description 18
- 239000000123 paper Substances 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000002699 waste material Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- SXUYADQBBAAFOO-UHFFFAOYSA-N dithiol-3-one Chemical compound O=C1C=CSS1 SXUYADQBBAAFOO-UHFFFAOYSA-N 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000002195 synergetic effect Effects 0.000 description 8
- 230000007423 decrease Effects 0.000 description 7
- 229940124561 microbicide Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000002855 microbicide agent Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- AFSROBHYIMWVTR-UHFFFAOYSA-N 1-(2-bromoacetyl)oxyethyl 2-bromoacetate Chemical compound BrCC(=O)OC(C)OC(=O)CBr AFSROBHYIMWVTR-UHFFFAOYSA-N 0.000 description 5
- WGHAPLWNJPAJDE-UHFFFAOYSA-N 2-(2-bromoacetyl)oxyethyl 2-bromoacetate Chemical compound BrCC(=O)OCCOC(=O)CBr WGHAPLWNJPAJDE-UHFFFAOYSA-N 0.000 description 5
- 241000589516 Pseudomonas Species 0.000 description 5
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 241000193830 Bacillus <bacterium> Species 0.000 description 4
- 244000063299 Bacillus subtilis Species 0.000 description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241000192041 Micrococcus Species 0.000 description 4
- 229940121375 antifungal agent Drugs 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 3
- 241000589565 Flavobacterium Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 125000001246 bromo group Chemical group Br* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000003113 dilution method Methods 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012770 industrial material Substances 0.000 description 2
- 239000008235 industrial water Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical compound C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 description 1
- AULPTOWQKPBHNZ-UHFFFAOYSA-N 1-(2-iodoacetyl)oxyethyl 2-iodoacetate Chemical compound ICC(=O)OC(C)OC(=O)CI AULPTOWQKPBHNZ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- ACZNQTYFQFELOO-UHFFFAOYSA-N 2-(2-chloroacetyl)oxybutyl 2-chloroacetate Chemical compound CCC(COC(=O)CCl)OC(=O)CCl ACZNQTYFQFELOO-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- REMUXBHTORVVPA-UHFFFAOYSA-N 2-bromoacetic acid;2-iodoacetic acid Chemical compound OC(=O)CBr.OC(=O)CI REMUXBHTORVVPA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BGIKAENNYCIKHC-UHFFFAOYSA-N 2-phenoxyethyl 2-chloroacetate Chemical compound ClCC(=O)OCCOC1=CC=CC=C1 BGIKAENNYCIKHC-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- WAONAUAMIAAYMS-UHFFFAOYSA-N 4-(2-bromoacetyl)oxybut-3-enyl 2-bromoacetate Chemical compound BrCC(=O)OCCC=COC(=O)CBr WAONAUAMIAAYMS-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000590020 Achromobacter Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- KYPRVTIXOCLOSM-UHFFFAOYSA-N BrCC(=O)OC(=C(C)OC(CBr)=O)C Chemical compound BrCC(=O)OC(=C(C)OC(CBr)=O)C KYPRVTIXOCLOSM-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000159512 Geotrichum Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000223259 Trichoderma Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- PMLYLCJICUMJEY-UHFFFAOYSA-N but-2-ene;ethane Chemical compound CC.CC=CC PMLYLCJICUMJEY-UHFFFAOYSA-N 0.000 description 1
- ZQICUYMRUVINIE-UHFFFAOYSA-N but-2-enyl 2-bromoacetate Chemical compound CC=CCOC(=O)CBr ZQICUYMRUVINIE-UHFFFAOYSA-N 0.000 description 1
- LDOGQJBJIGUTBQ-UHFFFAOYSA-N but-2-enyl 2-chloroacetate Chemical compound CC=CCOC(=O)CCl LDOGQJBJIGUTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8412879A JPS567701A (en) | 1979-07-02 | 1979-07-02 | Industrial germicidal and bacteriostatic composition |
| JP9829979A JPS5622702A (en) | 1979-07-31 | 1979-07-31 | Industrial sterilization and bacteriostasis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2460623A1 true FR2460623A1 (fr) | 1981-01-30 |
| FR2460623B1 FR2460623B1 (https=) | 1984-03-09 |
Family
ID=26425204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8014738A Granted FR2460623A1 (fr) | 1979-07-02 | 1980-07-02 | Composition microbicide/microbiostatique a base de 4,5-dichloro-1,2-dithiol-3-one et procede de destruction et/ou d'inhibition des microbes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4647577A (https=) |
| AU (1) | AU523121B2 (https=) |
| CA (1) | CA1143906A (https=) |
| DE (1) | DE3024911C2 (https=) |
| FI (1) | FI66721C (https=) |
| FR (1) | FR2460623A1 (https=) |
| GB (1) | GB2052989B (https=) |
| IT (1) | IT1130488B (https=) |
| SE (1) | SE447192B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5799507A (en) * | 1980-12-13 | 1982-06-21 | Katayama Chem Works Co Ltd | Industrial bactericidal and bacteriostatic composition |
| DE3436989C1 (de) * | 1984-10-09 | 1986-03-20 | Teroson Gmbh, 6900 Heidelberg | Mikroorganismen toetende oder das Wachstum von Mikroorganismen hemmende Zusammensetzung und deren Verwendung |
| DE3772966D1 (de) * | 1987-02-03 | 1991-10-17 | Grace W R & Co | Biozide. |
| EP0325396B1 (en) * | 1988-01-19 | 1991-07-03 | Yoshitomi Pharmaceutical Industries, Ltd. | Biocidal 4,5-dichloro-1,2-dithiol-3-one composition |
| US5026723A (en) * | 1988-04-18 | 1991-06-25 | Katayama Chemical, Inc. | Microbicidal/microbiostatic composition for industrial use |
| US5013755A (en) * | 1988-10-27 | 1991-05-07 | Somar Corporation | Germicidal composition |
| EP0370429A3 (en) * | 1988-11-21 | 1991-09-25 | Yoshitomi Pharmaceutical Industries, Ltd. | Microbicidal/microbistatic composition for industrial use and method of using the same |
| GB2238244A (en) * | 1989-11-21 | 1991-05-29 | Yoshitomi Pharmaceutical | Industrial microbicidal/microbistatic composition containing an n-alkylguanidin and 4,5-dichloro-1,2-dithiol-3-one |
| GB9023480D0 (en) * | 1990-10-29 | 1990-12-12 | Cambridge Technology & Science | Assay |
| FR2709678B1 (fr) * | 1993-09-09 | 1995-12-08 | David Philippe Marie | Procédé d'épuration d'effluents gazeux ou liquides contenant des dérivés soufrés. |
| US5681851A (en) * | 1995-06-07 | 1997-10-28 | Buckman Laboratories International, Inc. | Emulsified compositions of 1,4-bis(bromoacetoxy)-2-butene useful as a microbicide and preservative |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102174B (de) * | 1959-02-14 | 1961-03-16 | Albert Ag Chem Werke | Verfahren zur Herstellung von 5-Oxo-3, 4-dichlor-1, 2-dithiol |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH508579A (de) * | 1969-08-28 | 1971-06-15 | Stauffer Chemical Co | Verfahren zur Herstellung einer neuen biocid wirksamen Verbindung |
| US3879513A (en) * | 1971-07-12 | 1975-04-22 | Betz Laboratories | Synergistic combinations containing organo-bromine compounds and their use in the control of aerobacter aerogenes |
| US3839008A (en) * | 1971-07-12 | 1974-10-01 | Betz Laboratories | Slime control compositions containing organo-bromine compounds |
| JPS5647163B2 (https=) * | 1974-06-29 | 1981-11-07 | ||
| JPS5182723A (ja) * | 1975-01-16 | 1976-07-20 | Yoshitomi Pharmaceutical | Kogyoyosatsukinzaisoseibutsu |
| US4289581A (en) * | 1978-04-05 | 1981-09-15 | Katayama Chemical Works Co., Ltd. | Microbicidal slimicide compositions for industrial use |
-
1980
- 1980-06-25 AU AU59624/80A patent/AU523121B2/en not_active Expired
- 1980-06-26 CA CA000354931A patent/CA1143906A/en not_active Expired
- 1980-06-27 SE SE8004758A patent/SE447192B/sv not_active IP Right Cessation
- 1980-06-27 FI FI802073A patent/FI66721C/fi not_active IP Right Cessation
- 1980-06-30 GB GB8021356A patent/GB2052989B/en not_active Expired
- 1980-07-01 DE DE3024911A patent/DE3024911C2/de not_active Expired
- 1980-07-01 IT IT68033/80A patent/IT1130488B/it active
- 1980-07-02 FR FR8014738A patent/FR2460623A1/fr active Granted
-
1985
- 1985-12-20 US US06/815,174 patent/US4647577A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1102174B (de) * | 1959-02-14 | 1961-03-16 | Albert Ag Chem Werke | Verfahren zur Herstellung von 5-Oxo-3, 4-dichlor-1, 2-dithiol |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2052989B (en) | 1982-09-08 |
| DE3024911C2 (de) | 1986-07-31 |
| SE8004758L (sv) | 1981-02-19 |
| GB2052989A (en) | 1981-02-04 |
| FI66721B (fi) | 1984-08-31 |
| FR2460623B1 (https=) | 1984-03-09 |
| AU523121B2 (en) | 1982-07-15 |
| IT1130488B (it) | 1986-06-11 |
| AU5962480A (en) | 1982-01-07 |
| FI802073A7 (fi) | 1981-01-03 |
| DE3024911A1 (de) | 1981-01-29 |
| IT8068033A0 (it) | 1980-07-01 |
| US4647577A (en) | 1987-03-03 |
| SE447192B (sv) | 1986-11-03 |
| CA1143906A (en) | 1983-04-05 |
| FI66721C (fi) | 1984-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5670160A (en) | Preservatives and their use | |
| FR2460623A1 (fr) | Composition microbicide/microbiostatique a base de 4,5-dichloro-1,2-dithiol-3-one et procede de destruction et/ou d'inhibition des microbes | |
| CZ2000573A3 (cs) | Stabilizované směsi jodpropinylové sloučeniny s donorem formaldehydu | |
| CN100456932C (zh) | 游离甲醛低的稳定的醛供体和脱氢乙酸的增效抗菌组合物 | |
| FI92640C (fi) | Mikro-organismeja tappava/mikro-organismien kasvua estävä koostumus ja menetelmä sellaisen valmistamiseksi | |
| FR2503538A1 (fr) | Composition bactericide-bacteriostatique a usage industriel | |
| FR2495940A1 (fr) | Composition pour lutter contre les microbes comprenant de la 4,5-dichloro-1,2-dithiol-3-one et un alkylenebisthiocyanate, et son utilisation | |
| KR20020055432A (ko) | 할로시아노아세트아미드 항균 조성물 | |
| JP4621829B2 (ja) | 抗菌剤およびそれを用いた抗菌方法 | |
| WO2003013491A1 (en) | Synergistic microbicidal compositions | |
| CH619612A5 (https=) | ||
| AU731688B2 (en) | Dihaloformaldoxime carbamates as antimicrobial agents | |
| US3873711A (en) | Synergistic compositions for the control of aerobacter aerogenes | |
| RU2493875C2 (ru) | Стабилизированная противомикробная композиция | |
| FR2640116A1 (fr) | Composition biocide stable pour l'application industrielle | |
| BE1005156A3 (fr) | Composition hydrosoluble antiseptique ou antifongique. | |
| US5015660A (en) | Microbicidal/microbistatic composition for industrial use and method of using same | |
| FR2479215A1 (fr) | Oxo-2 halogeno-4 oxetannes et procede pour les preparer | |
| JPS6365641B2 (https=) | ||
| JP4157624B2 (ja) | スライムコントロール剤組成物及びスライムコントロール方法 | |
| JPH0242007A (ja) | 工業用殺菌、静菌剤 | |
| CH620337A5 (en) | Process for the preparation of nonmedicinal compositions resistant to degradation caused by the action of microorganisms | |
| JP3769592B2 (ja) | 工業用殺菌・静菌剤及び工業用殺菌・静菌方法 | |
| US3862324A (en) | Thiocyanate slime control composition and its use | |
| JP2959984B2 (ja) | 工業用殺菌・静菌剤及び工業用殺菌・静菌方法１ |