NO133308B - - Google Patents
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- Publication number
- NO133308B NO133308B NO4834/71A NO483471A NO133308B NO 133308 B NO133308 B NO 133308B NO 4834/71 A NO4834/71 A NO 4834/71A NO 483471 A NO483471 A NO 483471A NO 133308 B NO133308 B NO 133308B
- Authority
- NO
- Norway
- Prior art keywords
- bromo
- bromomethylglutaronitrile
- growth
- species
- bacteria
- Prior art date
Links
- DHVLDKHFGIVEIP-UHFFFAOYSA-N 2-bromo-2-(bromomethyl)pentanedinitrile Chemical compound BrCC(Br)(C#N)CCC#N DHVLDKHFGIVEIP-UHFFFAOYSA-N 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 14
- 230000000844 anti-bacterial effect Effects 0.000 claims description 9
- 239000003899 bactericide agent Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 description 16
- 230000012010 growth Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 241000233866 Fungi Species 0.000 description 12
- 239000000523 sample Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 241000195493 Cryptophyta Species 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 230000002353 algacidal effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000588915 Klebsiella aerogenes Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003619 algicide Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- -1 pulp Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 2
- 241000605739 Desulfovibrio desulfuricans Species 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000005791 algae growth Effects 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011868 grain product Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- XDONNFGLKABZET-UHFFFAOYSA-N 2,3-dichloroquinolin-8-ol Chemical compound ClC1=C(Cl)N=C2C(O)=CC=CC2=C1 XDONNFGLKABZET-UHFFFAOYSA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 229930183010 Amphotericin Natural products 0.000 description 1
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 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
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 241000194106 Bacillus mycoides Species 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- 241000186321 Cellulomonas Species 0.000 description 1
- 241000186318 Cellulomonas biazotea Species 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- 241001515917 Chaetomium globosum Species 0.000 description 1
- 244000249214 Chlorella pyrenoidosa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000605716 Desulfovibrio Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000813090 Rhizoctonia solani Species 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- KSQXVLVXUFHGJQ-UHFFFAOYSA-M Sodium ortho-phenylphenate Chemical compound [Na+].[O-]C1=CC=CC=C1C1=CC=CC=C1 KSQXVLVXUFHGJQ-UHFFFAOYSA-M 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241001136508 Talaromyces luteus Species 0.000 description 1
- 241000223259 Trichoderma Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229940009444 amphotericin Drugs 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical class [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- OPGYRRGJRBEUFK-UHFFFAOYSA-L disodium;diacetate Chemical compound [Na+].[Na+].CC([O-])=O.CC([O-])=O OPGYRRGJRBEUFK-UHFFFAOYSA-L 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
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229940049018 mycostatin Drugs 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative 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
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical class [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000017454 sodium diacetate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000010294 sodium orthophenyl phenol Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 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
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 229930188428 trichomycin Natural products 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012138 yeast extract 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Materials Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00102197A US3833731A (en) | 1970-12-28 | 1970-12-28 | Dihalomethylglutaronitriles used as antibacterial and antifungal agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133308B true NO133308B (xx) | 1976-01-05 |
| NO133308C NO133308C (xx) | 1976-04-12 |
Family
ID=22288630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4834/71A NO133308C (xx) | 1970-12-28 | 1971-12-27 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3833731A (xx) |
| AT (1) | AT313635B (xx) |
| AU (1) | AU459234B2 (xx) |
| BE (1) | BE777325A (xx) |
| CA (1) | CA967880A (xx) |
| DE (1) | DE2164723C3 (xx) |
| DK (1) | DK135972B (xx) |
| FI (1) | FI51278C (xx) |
| FR (1) | FR2120068B1 (xx) |
| GB (1) | GB1333317A (xx) |
| HK (1) | HK66176A (xx) |
| IE (1) | IE35894B1 (xx) |
| IL (1) | IL38349A (xx) |
| NL (1) | NL173519C (xx) |
| NO (1) | NO133308C (xx) |
| PH (1) | PH10631A (xx) |
| ZA (1) | ZA718595B (xx) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3929858A (en) * | 1974-12-03 | 1975-12-30 | Merck & Co Inc | Method for preparing 2-bromo-2-bromomethyl-glutaronitrile |
| US4397851A (en) * | 1981-12-22 | 1983-08-09 | Merck & Co., Inc. | 2,3-Dihalo-2,3-(disubstituted) propanoate antimicrobial compounds |
| US4366170A (en) * | 1981-12-22 | 1982-12-28 | Merck & Co., Inc. | 1,2-Dibromo-2-cyano-2-(aryl)ethane(propane) antimicrobial compounds |
| US4442122A (en) * | 1981-12-22 | 1984-04-10 | Merck & Co., Inc. | 1,2-Dibromo-2-cyanoalkane antimicrobial compounds |
| US4496581A (en) * | 1981-12-22 | 1985-01-29 | Merck & Co., Inc. | 1,2-Dibromo-2-cyano-2-(heterocyclic)alkane compounds and antimicrobial use thereof |
| EP0098410B1 (en) * | 1982-06-21 | 1985-11-21 | Merck & Co. Inc. | Synergistic antimicrobial combination |
| JPS59210057A (ja) * | 1983-05-12 | 1984-11-28 | Mitsubishi Yuka Fine Chem Co Ltd | ジブロモ−ジシアノブタンの精製法 |
| US4503074A (en) * | 1983-08-08 | 1985-03-05 | Merck & Co., Inc. | Halogenated geminal diesters |
| US4612328A (en) * | 1984-12-07 | 1986-09-16 | Calgon Corporation | Admixtures of 2-bromo-2-bromomethylglutaronitrile and methylene bis(thiocyanate) |
| US4655815A (en) * | 1985-03-27 | 1987-04-07 | Calgon Corporation | Admixtures of 2-bromo-2-bromomethylglutaronitrile and a formaldehyde donor |
| CA1272001A (en) * | 1985-03-04 | 1990-07-31 | John A. Jakubowski | Synergistic admixtures containing 2-bromo-2- bromomethylglutaronitrile |
| US4604405A (en) * | 1985-03-04 | 1986-08-05 | Calgon Corporation | Admixtures of 2-bromo-2-bromomethylglutaronitrile and 2,2-dibromo-3-nitrilopropionamide |
| US5034405A (en) * | 1985-03-27 | 1991-07-23 | Calgon Corporation | Admixtures of 2-bromo-2-bromomethyl-glutaronitrile, 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one |
| US4968323A (en) * | 1987-11-02 | 1990-11-06 | Mobil Oil Corporation | Metalworking fluid composition |
| GB9009529D0 (en) * | 1990-04-27 | 1990-06-20 | Ici Plc | Biocide composition and use |
| US5124355A (en) * | 1990-11-28 | 1992-06-23 | W. R. Grace & Co.-Conn. | Synergistic microbiocidal composition of 2-(decylthio)ethaneamine and 1,2-dibromo-2,4-dicyanobutane |
| US5246963A (en) * | 1992-07-24 | 1993-09-21 | Great Lakes Chemical Corp. | Synergistic antimicrobial compositions containing 2-(2-bromo-2-nitroethenyl)furan |
| US5457083A (en) * | 1992-10-15 | 1995-10-10 | Calgon Corporation | Synergistic antimicrobial combination of polyether phosphonates and non-oxidizing biocides |
| JP3230381B2 (ja) * | 1994-08-04 | 2001-11-19 | ダイキン工業株式会社 | フッ素系ポリマー水性分散液 |
| DE19521240A1 (de) * | 1995-06-10 | 1996-12-12 | Beiersdorf Ag | Antimycotische Zubereitungen mit einem wirksamen Gehalt an Nitrilen und Arylverbindungen |
| US6090832A (en) * | 1995-07-31 | 2000-07-18 | Calgon Corporation | Process for making antimicrobial agents in aqueous dispersion form containing 2-(4-thiazolyl)-benzimidazole alone or in combination with 1,2-dibromo-2,4-dicyanobutane |
| US5700834A (en) | 1995-08-31 | 1997-12-23 | Calgon Corporation | Synergistic antimicrobial composition of 1,2-dibromo-2,4-dicyanobutaneand alkylguanidine compounds |
| US5641808A (en) * | 1995-09-01 | 1997-06-24 | Calgon Corporation | Synergistic antimicrobial composition of 1,2-dibromo-2,4-dicyanobutane and esters of parahydroxybenzoic acid |
| US5985934A (en) * | 1996-04-22 | 1999-11-16 | Calgon Corporation | Synergistic antimicrobial composition of 2,4,4'-trichloro-2'-hydroxydiphenyl ether and 1,2-dibromo-2,4-dicyanobutane |
| US5763482A (en) * | 1997-03-20 | 1998-06-09 | Betzdearborn Inc. | Biocidal composition and use |
| US6039004A (en) * | 1998-02-13 | 2000-03-21 | Oil-Dri Corporation Of America | Cellulosic animal litter product |
| DE10008507A1 (de) * | 2000-02-24 | 2001-08-30 | Bayer Ag | Mikrobizide Mittel |
| JP4506068B2 (ja) * | 2001-09-26 | 2010-07-21 | ケイ・アイ化成株式会社 | 工業用殺菌防腐剤及び殺菌防腐方法 |
| US6878373B2 (en) * | 2001-12-03 | 2005-04-12 | Micropure Technologies, Inc. | Probiotic composition containing Bacillus cereus RRRL B-30535 |
| US6548692B1 (en) | 2002-04-25 | 2003-04-15 | Isp Investments Inc. | Method for preparing 1,2-dibromo-2,4-dicyanobutane |
| US6562993B1 (en) | 2002-05-10 | 2003-05-13 | Isp Investments Inc. | Preservative compounds |
| GB2392167A (en) * | 2002-08-22 | 2004-02-25 | Reckitt Benckiser Inc | Composition containing an acid with anionic and nonionic surfactants |
| UA116760C2 (uk) | 2011-04-07 | 2018-05-10 | Біі Векторінг Течнолоґи Інк. | Пристрій для обробки рослин |
| EP2825049A4 (en) | 2012-03-12 | 2015-09-02 | Bee Vectoring Technology Inc | FORMULATION WITH A PARTICULATE CALCIUM SILICATE AND CLOSED ROSEA FOR THE TREATMENT OF PLANTS |
-
1970
- 1970-12-28 US US00102197A patent/US3833731A/en not_active Expired - Lifetime
-
1971
- 1971-12-09 NL NLAANVRAGE7116918,A patent/NL173519C/xx not_active IP Right Cessation
- 1971-12-13 IE IE1577/71A patent/IE35894B1/xx unknown
- 1971-12-14 AU AU36845/71A patent/AU459234B2/en not_active Expired
- 1971-12-14 CA CA130,144A patent/CA967880A/en not_active Expired
- 1971-12-14 FI FI713554A patent/FI51278C/fi active
- 1971-12-14 IL IL38349A patent/IL38349A/xx unknown
- 1971-12-17 AT AT1087371A patent/AT313635B/de not_active IP Right Cessation
- 1971-12-20 PH PH13123A patent/PH10631A/en unknown
- 1971-12-20 GB GB5904871A patent/GB1333317A/en not_active Expired
- 1971-12-23 ZA ZA718595A patent/ZA718595B/xx unknown
- 1971-12-27 DE DE2164723A patent/DE2164723C3/de not_active Expired
- 1971-12-27 BE BE777325A patent/BE777325A/xx not_active IP Right Cessation
- 1971-12-27 NO NO4834/71A patent/NO133308C/no unknown
- 1971-12-27 DK DK634671AA patent/DK135972B/da not_active IP Right Cessation
- 1971-12-28 FR FR7146998A patent/FR2120068B1/fr not_active Expired
-
1976
- 1976-10-21 HK HK661/76*UA patent/HK66176A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE35894L (en) | 1972-06-28 |
| NL173519B (nl) | 1983-09-01 |
| FR2120068B1 (xx) | 1975-03-14 |
| DE2164723A1 (de) | 1972-08-03 |
| GB1333317A (en) | 1973-10-10 |
| IE35894B1 (en) | 1976-06-23 |
| NL7116918A (xx) | 1972-06-30 |
| AT313635B (de) | 1974-02-25 |
| HK66176A (en) | 1976-10-29 |
| NL173519C (nl) | 1984-02-01 |
| PH10631A (en) | 1977-07-21 |
| DK135972C (xx) | 1978-01-02 |
| DE2164723C3 (de) | 1980-11-06 |
| IL38349A0 (en) | 1972-03-28 |
| DE2164723B2 (de) | 1980-03-13 |
| FR2120068A1 (xx) | 1972-08-11 |
| FI51278B (xx) | 1976-08-31 |
| NO133308C (xx) | 1976-04-12 |
| FI51278C (fi) | 1976-12-10 |
| AU3684571A (en) | 1973-06-21 |
| IL38349A (en) | 1974-10-22 |
| BE777325A (fr) | 1972-06-27 |
| ZA718595B (en) | 1973-08-29 |
| DK135972B (da) | 1977-07-25 |
| AU459234B2 (en) | 1975-03-20 |
| CA967880A (en) | 1975-05-20 |
| US3833731A (en) | 1974-09-03 |
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