CA1156247A - 4-halogeno-oxetan-2-ones et procede de production - Google Patents

4-halogeno-oxetan-2-ones et procede de production

Info

Publication number: CA1156247A
Authority: CA; Canada
Prior art keywords: compound; chlorine; oxetan; atom; group
Prior art date: 1981-03-03
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

Application number

CA000372185A

Other languages

English (en)

Inventor

John G. Dingwall

Brian Tuck

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.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1981-03-03

Filing date

1981-03-03

Publication date

1983-11-01

1981-03-03 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1981-03-03 Priority to CA000372185A priority Critical patent/CA1156247A/fr

1983-11-01 Application granted granted Critical

1983-11-01 Publication of CA1156247A publication Critical patent/CA1156247A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 28
229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
239000000460 chlorine Substances 0.000 claims abstract description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 12
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
239000003795 chemical substances by application Substances 0.000 claims abstract description 6
239000011737 fluorine Chemical group 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052740 iodine Chemical group 0.000 claims abstract description 3
HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical compound [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical group ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 26
229950005499 carbon tetrachloride Drugs 0.000 claims description 13
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 claims description 12
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
-1 trihalomethyl compound Chemical class 0.000 claims description 6
150000001451 organic peroxides Chemical class 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
230000005855 radiation Effects 0.000 claims description 4
KHFABQFEJXAPJQ-UHFFFAOYSA-N 4-bromo-4-(2,2,2-tribromoethyl)oxetan-2-one Chemical compound BrC(Br)(Br)CC1(Br)CC(=O)O1 KHFABQFEJXAPJQ-UHFFFAOYSA-N 0.000 claims description 3
IAUUXUPPUOCYTN-UHFFFAOYSA-N 4-bromo-4-(2,2,2-trichloroethyl)oxetan-2-one Chemical compound ClC(Cl)(Cl)CC1(Br)CC(=O)O1 IAUUXUPPUOCYTN-UHFFFAOYSA-N 0.000 claims description 3
DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 claims description 2
XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 claims description 2
230000002844 continuous effect Effects 0.000 claims description 2
VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 2
238000009740 moulding (composite fabrication) Methods 0.000 claims 2
229940089960 chloroacetate Drugs 0.000 claims 1
241000195493 Cryptophyta Species 0.000 abstract description 10
239000000203 mixture Substances 0.000 abstract description 10
241000894006 Bacteria Species 0.000 abstract description 6
241000233866 Fungi Species 0.000 abstract description 3
239000002519 antifouling agent Substances 0.000 abstract description 3
SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 abstract 1
125000004429 atom Chemical group 0.000 abstract 1
150000003254 radicals Chemical class 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
BVWKKDBTTFIKCM-UHFFFAOYSA-N 4-chloro-4-(2,2,2-trichloroethyl)oxetan-2-one Chemical compound ClC(Cl)(Cl)CC1(Cl)CC(=O)O1 BVWKKDBTTFIKCM-UHFFFAOYSA-N 0.000 description 5
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000003139 biocide Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
SJMLNDPIJZBEKY-UHFFFAOYSA-N ethyl 2,2,2-trichloroacetate Chemical compound CCOC(=O)C(Cl)(Cl)Cl SJMLNDPIJZBEKY-UHFFFAOYSA-N 0.000 description 3
BBSUDXNAOJEPRE-UHFFFAOYSA-N ethyl 2,2-dichloro-3-(2-chloro-4-oxooxetan-2-yl)propanoate Chemical compound CCOC(=O)C(Cl)(Cl)CC1(Cl)CC(=O)O1 BBSUDXNAOJEPRE-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000194106 Bacillus mycoides Species 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
241000588915 Klebsiella aerogenes Species 0.000 description 2
241000215468 Leptolyngbya foveolarum Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000589517 Pseudomonas aeruginosa Species 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
241000199473 Tribonema aequale Species 0.000 description 2
239000000654 additive Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
229960003328 benzoyl peroxide Drugs 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
239000003643 water by type Substances 0.000 description 2
NIKYWVNPUSCNSI-UHFFFAOYSA-N 2,2-dibromo-3-(2-bromo-4-oxooxetan-2-yl)propanenitrile Chemical compound N#CC(Br)(Br)CC1(Br)CC(=O)O1 NIKYWVNPUSCNSI-UHFFFAOYSA-N 0.000 description 1
SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
UDIWTROLKQLGOI-UHFFFAOYSA-N 4-bromo-4-(2-bromo-2,2-dichloroethyl)oxetan-2-one Chemical compound ClC(Cl)(Br)CC1(Br)CC(=O)O1 UDIWTROLKQLGOI-UHFFFAOYSA-N 0.000 description 1
ISFFNKQBLGMXKR-UHFFFAOYSA-N 4-bromo-4-(2-bromo-2,2-difluoroethyl)oxetan-2-one Chemical compound FC(F)(Br)CC1(Br)CC(=O)O1 ISFFNKQBLGMXKR-UHFFFAOYSA-N 0.000 description 1
IWHRTEYEHDZCJO-UHFFFAOYSA-N 4-bromo-4-(2-bromo-2-chloro-3,3,3-trifluoropropyl)oxetan-2-one Chemical compound FC(F)(F)C(Cl)(Br)CC1(Br)CC(=O)O1 IWHRTEYEHDZCJO-UHFFFAOYSA-N 0.000 description 1
ZWLPTXYXJZQDNV-UHFFFAOYSA-N 4-chloro-4-(2,2,3,3,3-pentachloropropyl)oxetan-2-one Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)CC1(Cl)CC(=O)O1 ZWLPTXYXJZQDNV-UHFFFAOYSA-N 0.000 description 1
WSCBESJRHKNLHU-UHFFFAOYSA-N 4-iodo-4-(2,2,2-trifluoroethyl)oxetan-2-one Chemical compound FC(F)(F)CC1(I)CC(=O)O1 WSCBESJRHKNLHU-UHFFFAOYSA-N 0.000 description 1
241001453369 Achromobacter denitrificans Species 0.000 description 1
241000223602 Alternaria alternata Species 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000223678 Aureobasidium pullulans Species 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000195649 Chlorella <Chlorellales> Species 0.000 description 1
240000009108 Chlorella vulgaris Species 0.000 description 1
235000007089 Chlorella vulgaris Nutrition 0.000 description 1
241000195628 Chlorophyta Species 0.000 description 1
241001149955 Cladosporium cladosporioides Species 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
229910015400 FeC13 Inorganic materials 0.000 description 1
240000008397 Ganoderma lucidum Species 0.000 description 1
244000168141 Geotrichum candidum Species 0.000 description 1
235000017388 Geotrichum candidum Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000761677 Jaaginema geminatum Species 0.000 description 1
241001086185 Klebsormidium subtilissimum Species 0.000 description 1
241000192656 Nostoc Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000195663 Scenedesmus Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
241000187392 Streptomyces griseus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000192589 Synechococcus elongatus PCC 7942 Species 0.000 description 1
241001136494 Talaromyces funiculosus Species 0.000 description 1
241000199474 Tribonema Species 0.000 description 1
241000159614 Ulothrix Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003619 algicide Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002173 cutting fluid Substances 0.000 description 1
235000013365 dairy product Nutrition 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
239000007970 homogeneous dispersion Substances 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000012994 industrial processing Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
YNJGQFYHEYGTRG-UHFFFAOYSA-N methyl 2,2-dichloro-3-(2-chloro-4-oxooxetan-2-yl)propanoate Chemical compound COC(=O)C(Cl)(Cl)CC1(Cl)CC(=O)O1 YNJGQFYHEYGTRG-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920001444 polymaleic acid Polymers 0.000 description 1
230000004224 protection Effects 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Inorganic materials [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000009182 swimming Effects 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 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
125000004953 trihalomethyl group Chemical group 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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Epoxy Compounds (AREA)

CA000372185A 1981-03-03 1981-03-03 4-halogeno-oxetan-2-ones et procede de production Expired CA1156247A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000372185A CA1156247A (fr)	1981-03-03	1981-03-03	4-halogeno-oxetan-2-ones et procede de production

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000372185A CA1156247A (fr)	1981-03-03	1981-03-03	4-halogeno-oxetan-2-ones et procede de production

Publications (1)

Publication Number	Publication Date
CA1156247A true CA1156247A (fr)	1983-11-01

Family

ID=4119364

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000372185A Expired CA1156247A (fr)	1981-03-03	1981-03-03	4-halogeno-oxetan-2-ones et procede de production

Country Status (1)

Country	Link
CA (1)	CA1156247A (fr)

1981
- 1981-03-03 CA CA000372185A patent/CA1156247A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-11-01	MKEX	Expiry

Publication	Publication Date	Title
US5057612A (en)	1991-10-15	N,n'-dihaloimidazolidin-4-ones
EP0239896B1 (fr)	1990-09-05	N,N'-Dihalogéno imidazolidinone-2
US4719083A (en)	1988-01-12	Composition useful as corrosion inhibitor, anti-scalant and continuous biocide for water cooling towers and method of use
US5126057A (en)	1992-06-30	Disinfecting with N,N'-dihaloimidazolidin-4-ones
AU2001258644B2 (en)	2005-06-02	Treatment of circulating water systems
CA2108183C (fr)	2004-07-20	Combinaison antimicrobienne synergique de phosphonates de polyether et de biocides non oxydants
AU614511B2 (en)	1991-09-05	Biocide
US4363923A (en)	1982-12-14	4-Halgeno-oxetan-2-ones and process for their production
EP0364789B1 (fr)	1993-03-10	Composition antimicrobienne et méthode d'utilisation
CA1156247A (fr)	1983-11-01	4-halogeno-oxetan-2-ones et procede de production
US3864253A (en)	1975-02-04	Slime control compositions and their use
CA1295549C (fr)	1992-02-11	Composes de type ylure d'iodonium utilises comme agents antimicrobiens
GB2072669A (en)	1981-10-07	Biocidal 4-halooxetan-2-one derivatives
JP3562825B2 (ja)	2004-09-08	殺菌殺藻剤
CN104705299A (zh)	2015-06-17	二溴丙二酰胺的组合物及其作为杀生物剂的用途
US4397851A (en)	1983-08-09	2,3-Dihalo-2,3-(disubstituted) propanoate antimicrobial compounds
US3973945A (en)	1976-08-10	Pyran-2,4-dione derivatives
US4028394A (en)	1977-06-07	Antibacterial and fungicidal S-phenylthiocarbamates
US3953478A (en)	1976-04-27	Tetrahydrofuranyl bromoacetates biocides
US4086076A (en)	1978-04-25	Tetrahydrofuranyl bromoacetates used as biocides
US3987195A (en)	1976-10-19	Certain bromoacetoxy acetylenes used as bactericides
JPS6023344A (ja)	1985-02-05	２，３−ジハロ−２，３−（ジ置換）プロパンエ−ト抗菌化合物
Direktor et al.	1991	Dialkylphosphonodibromo‐acetates and‐acetonitriles as potential new biocides
Biocides et al.	0	Dialkylphosphonodibromo-Acetates and-Acetonitriles as
DE1959841A1 (de)	1970-07-16	Bis-(polyhalogenkohlenwasserstoff)-trisulfide