NO860844L - Nye jodpropargyletere, en fremgangsmaate til deres fremstilling og deres anvendelse. - Google Patents
Nye jodpropargyletere, en fremgangsmaate til deres fremstilling og deres anvendelse.Info
- Publication number
- NO860844L NO860844L NO860844A NO860844A NO860844L NO 860844 L NO860844 L NO 860844L NO 860844 A NO860844 A NO 860844A NO 860844 A NO860844 A NO 860844A NO 860844 L NO860844 L NO 860844L
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- new
- hydrogen
- formula
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- LKYMWFDXBHLYNJ-UHFFFAOYSA-N 3-iodo-3-(1-iodoprop-2-ynoxy)prop-1-yne Chemical class C#CC(I)OC(I)C#C LKYMWFDXBHLYNJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000026045 iodination Effects 0.000 claims description 5
- 238000006192 iodination reaction Methods 0.000 claims description 5
- 239000002855 microbicide agent Substances 0.000 claims description 5
- 239000002023 wood Substances 0.000 claims description 4
- ZLUDXJKMZXJQRT-UHFFFAOYSA-N 3-iodoprop-2-ynoic acid Chemical class OC(=O)C#CI ZLUDXJKMZXJQRT-UHFFFAOYSA-N 0.000 claims description 3
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- -1 propargyl halides Chemical class 0.000 description 9
- 235000015097 nutrients Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000002440 hydroxy compounds Chemical class 0.000 description 7
- HRDCVMSNCBAMAM-UHFFFAOYSA-N 3-prop-2-ynoxyprop-1-yne Chemical class C#CCOCC#C HRDCVMSNCBAMAM-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KIOKAVGATXNYJX-UHFFFAOYSA-N 2-iodo-2-(prop-2-ynoxymethyl)oxolane Chemical compound C#CCOCC1(I)CCCO1 KIOKAVGATXNYJX-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- OMNGRPHPKWAMSY-UHFFFAOYSA-N 1-chloroprop-1-yne Chemical compound CC#CCl OMNGRPHPKWAMSY-UHFFFAOYSA-N 0.000 description 2
- DKJUYYRGJJGNDE-UHFFFAOYSA-N 2-ethyl-4-[iodo(prop-2-ynoxy)methyl]-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCC(C(I)OCC#C)O1 DKJUYYRGJJGNDE-UHFFFAOYSA-N 0.000 description 2
- DYEKUANGUUKLNZ-UHFFFAOYSA-N 4-[iodo(prop-2-ynoxy)methyl]-2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCC(C(I)OCC#C)O1 DYEKUANGUUKLNZ-UHFFFAOYSA-N 0.000 description 2
- KHJCWHZXUSOFCM-UHFFFAOYSA-N 4-[iodo(prop-2-ynoxy)methyl]-2-phenyl-1,3-dioxolane Chemical compound O1C(C(OCC#C)I)COC1C1=CC=CC=C1 KHJCWHZXUSOFCM-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 235000019270 ammonium chloride Nutrition 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
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000011111 cardboard Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000005068 cooling lubricant Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 150000002012 dioxanes Chemical class 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003408 phase transfer catalysis Methods 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000007984 tetrahydrofuranes Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZAIRCVNISFRBHW-UHFFFAOYSA-N 1h-benzimidazol-2-yl n-methylcarbamate Chemical class C1=CC=C2NC(OC(=O)NC)=NC2=C1 ZAIRCVNISFRBHW-UHFFFAOYSA-N 0.000 description 1
- XSFDIUOTZKUUCJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-iodo-2-prop-2-ynoxy-1,3-dioxane Chemical compound C1=CC(Cl)=CC=C1C1(OCC#C)OCC(I)CO1 XSFDIUOTZKUUCJ-UHFFFAOYSA-N 0.000 description 1
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
- FJZNTVAFRRVDLS-UHFFFAOYSA-N 2-iodo-2-(prop-2-ynoxymethyl)oxane Chemical compound C#CCOCC1(I)CCCCO1 FJZNTVAFRRVDLS-UHFFFAOYSA-N 0.000 description 1
- 229940061334 2-phenylphenol Drugs 0.000 description 1
- PBGQALIOYYRQLL-UHFFFAOYSA-N 3-(1-iodoprop-2-ynoxy)propane-1,2-diol Chemical compound OCC(O)COC(I)C#C PBGQALIOYYRQLL-UHFFFAOYSA-N 0.000 description 1
- KCIPPSRDFCSKLJ-UHFFFAOYSA-N 3-(3-iodoprop-2-ynoxy)propane-1,2-diol Chemical compound OCC(O)COCC#CI KCIPPSRDFCSKLJ-UHFFFAOYSA-N 0.000 description 1
- BWMDSPHSDMRGQQ-UHFFFAOYSA-N 3-ethyl-3-iodo-2-(prop-2-ynoxymethyl)oxetane Chemical compound CCC1(I)COC1COCC#C BWMDSPHSDMRGQQ-UHFFFAOYSA-N 0.000 description 1
- BMVHZOFGEAEKSI-UHFFFAOYSA-N 3-iodo-2-prop-2-ynoxyoxolane Chemical compound IC1CCOC1OCC#C BMVHZOFGEAEKSI-UHFFFAOYSA-N 0.000 description 1
- WVINLIJIZJSRPL-UHFFFAOYSA-N 3-iodo-3-methyl-2-(prop-2-ynoxymethyl)oxetane Chemical compound CC1(I)COC1COCC#C WVINLIJIZJSRPL-UHFFFAOYSA-N 0.000 description 1
- HGYGTQVOYVPFSI-UHFFFAOYSA-N 4-(4-iodo-4-prop-2-ynoxybutyl)-2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCC(CCCC(I)OCC#C)O1 HGYGTQVOYVPFSI-UHFFFAOYSA-N 0.000 description 1
- BDUCQGKYFLPGII-UHFFFAOYSA-N 4-[iodo(prop-2-ynoxy)methyl]-2-methyl-1,3-dioxolane Chemical compound CC1OCC(C(I)OCC#C)O1 BDUCQGKYFLPGII-UHFFFAOYSA-N 0.000 description 1
- CPACJVSRHMTWAD-UHFFFAOYSA-N 4-iodo-2-(prop-2-ynoxymethyl)-1,3-dioxolane Chemical compound IC1COC(COCC#C)O1 CPACJVSRHMTWAD-UHFFFAOYSA-N 0.000 description 1
- SPESEFUPLOTNQC-UHFFFAOYSA-N 5-ethyl-5-iodo-2,2-dimethyl-4-(prop-2-ynoxymethyl)-1,3-dioxane Chemical compound CCC1(I)COC(C)(C)OC1COCC#C SPESEFUPLOTNQC-UHFFFAOYSA-N 0.000 description 1
- RNTSTUJCGRIRKM-UHFFFAOYSA-N 5-ethyl-5-iodo-2-(prop-2-ynoxymethyl)-1,3-dioxane Chemical compound CCC1(I)COC(COCC#C)OC1 RNTSTUJCGRIRKM-UHFFFAOYSA-N 0.000 description 1
- RIBCKQRLQDPCAG-UHFFFAOYSA-N 5-iodo-2,2,5-trimethyl-4-(prop-2-ynoxymethyl)-1,3-dioxane Chemical compound CC1(C)OCC(C)(I)C(COCC#C)O1 RIBCKQRLQDPCAG-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria 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
- 241000223651 Aureobasidium Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 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
- 235000007091 Chlorella pyrenoidosa Nutrition 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241001600093 Coniophora Species 0.000 description 1
- 241001600095 Coniophora puteana Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000195619 Euglena gracilis Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 241000761677 Jaaginema geminatum Species 0.000 description 1
- 241000222418 Lentinus Species 0.000 description 1
- 241000222451 Lentinus tigrinus Species 0.000 description 1
- 241000215468 Leptolyngbya foveolarum Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 241001123663 Penicillium expansum Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000206744 Phaeodactylum tricornutum Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000222640 Polyporus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241001504046 Stichococcus bacillaris Species 0.000 description 1
- 241000907561 Sydowia polyspora Species 0.000 description 1
- 241000222355 Trametes versicolor Species 0.000 description 1
- 241000223259 Trichoderma Species 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- 230000005791 algae growth Effects 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000005587 bubbling 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JWZXKXIUSSIAMR-UHFFFAOYSA-N methylene bis(thiocyanate) Chemical compound N#CSCSC#N JWZXKXIUSSIAMR-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
- A01N43/04—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 one hetero atom
- A01N43/06—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 one hetero atom five-membered rings
- A01N43/08—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 one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/04—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 one hetero atom
- A01N43/14—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 one hetero atom six-membered rings
- A01N43/16—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 one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/04—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 one hetero atom
- A01N43/20—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 one hetero atom three- or four-membered rings
-
- 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
- A01N43/28—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 with two hetero atoms in positions 1,3
-
- 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
- A01N43/28—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 with two hetero atoms in positions 1,3
- A01N43/30—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 with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
-
- 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
- A01N43/32—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 six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Epoxy Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
Oppfinnelsen vedrører nye jodpropargyletere, en fremgangsmåte til deres fremstilling og deres anvendelse i mikrobizide midler.
Fra De-OS 3 304 899 er det kjent å anvende jodpropargyletere som 1-(3-jod-2-propinyloksy)-propan-2,3-diol som antimikro-bielle stoffer. Uheldig er deres ikke alltid tilfredsstill-ende virkning.
Det er funnet nye jodpropargyletere med formel
hvori
A betyr oksygen eller en metylengruppe,
R<1>betyr hydrogen, eller laverealkyl,
R 2 og R 3 er like eller forskjellige og betyr hydrogen, laverealkyl, alkenyl eller en eventuelt med halogen substituert fenyl, eller sammen danner en karbocyklisk ring med 4 til 7 karbonatomer,
1 og m betyr 0, 1 eller 2,
n betyr et helt tall fra 0 til 4, med den forholdsregel at når 1 erO, betyr n 1, 2, 3 eller 4, og
k betyr 0 eller 1.
Ifølge oppfinnelsen betyr laverealkyl vanligvis en rettlinjet eller forgrenet hydrokarbonrest med 1 til 6 karbonatomer, fortrinnsvis' 1 til 4 karbonatomer. I detalj skal det nevnes: metyl, etyl, propyl, isopropyl, butyl, isobutyl, pentyl, iso-pentyl, heksyl eller isoheksyl. Foretrukket er metyl-, og etylrester..
Halogen betyr ifølge oppfinnelsen fluor, klor, brom og jod, fortrinnsvis klor.
Hvis R 2 og R 3 sammen danner en karbocyklisk ring, så er det foretrukket en karbocyklisk ring med 5 til 6 karbonatomer.
Foretrukket • nye jodpropargyletere er slike med formel
hvori
A betyr oksygen eller en metylengruppe,
R 4betyr hydrogen eller laverealkyl,
R 5 betyr hydrogen, laverealkyl, fenyl eller klorfenyl,
1 og m betyr 0, 1 eller 2, og
k betyr 0 eller 1.
Eksempelvis skal det nevnes de følgende nye jodpropargyletere: 2- (4-klorfenyl)-5-jodpropargyloksy-1,3-dioksan, 2,2-dimetyl-4- (4-jodpropargyloksybutyl)-1,3-dioksolan,
5- etyl-5-jodpropargyloksymetyl-1,3-dioksan,
2,2-dimetyl-5-etyl-5-jodpropargyloksymetyl-1,3-dioksan, 2,2,5-trimetyl-5-jodpropargyloksymetyl-1,3-dioksan, 3- jodpropargyloksy-tetrahydrofuran,
3-metyl-3-jodpropargyloksymetyl-oksetan,
3- etyl-3-jodpropargyloksymetyl-oksetan,
4- jodpropargyloksymetyl-1,3-dioksolan,
2-metyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2,2-dimetyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2-mety l-2-etyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2,2-pentametylen-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2-fenyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2-jodpropargyloksymetyl-tetrahydrofuran,
2-jodpropargyloksymetyl-tetrahydropyran og
2-metyl-2-fenyl-4-(jodpropargyloksymetyl)-1,3-
dioksolan, foretrukket
4-(jodpropargyloksymetyl-1,3-dioksolan,
2-mety 1-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2,2-dimetyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2-mety l-2-etyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2,2-pentametylen-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2-fenyl-4-(jodpropargyloksymetyl)-1,3-dioksolan, 2-jodpropargyloksymetyl-tetrahydrofuran,
2-jodpropargyloksymetyl-tetrahydrofuran og
2-metyl-2-fenyl-4-(jodpropargyloksymetyl)-1,3-
dioksolan.
Videre er det funnet en fremgangsmåte til fremstilling av de nye jodpropargyletere med formel
hvori
A betyr oksygen eller en metylengruppe.,
R"1" betyr hydrogen, eller laverealkyl,
2 3
R og R er like eller forskjellige og betyr hydrogen,
laverealkyl, alkenyl eller eventuelt med halogen substituert fenyl, eller sammen danner en karbocyklisk ring med 4 til 7 karbonatomer,
1 og m betyr 0, 1 eller 2,
n betyr et helt tall fra 0 til 4, med den forholdsregel at
når 1=0, betyr n 1, 2,3 eller 4, og
k betyr 0 eller 1,
idet fremgangsmåten erkarakterisert vedat propargyletere med formel
hvori
12 3
A, R, R, R, l,m, nogk har overnevnte betydning, omsettes med joderingsmiddel i nærvær av oppløsnings- og/ eller fortynningsmidler og i nærvær av baser ved temperaturer fra -10 til 30°C.
Som joderingsmidler kan det i fremgangsmåten ifølge oppfinnelsen anvendes jod, og/eller jodidionleverende forbindelser som natrjumjodid og ammoniumjodid i nærvær av oksydasjons-midler som natriumhypoklorit, kalsiumhypoklorit eller hydro-genperoksyd.
Som baser egner det seg såvel uorganiske som også organiske baser, som natriumhydroksyd, kalsiumhydroksyd, natriummetylat, kalium-tert.-butylat og natriumisobutylat, fortrinnsvis natriumhydroksyd og natriummetylat.
Egnede oppløsningsmidler for fremgangsmåten ifølge oppfinnelsen er eksempelvis vann eller alkoholer, som metanol og/ eller etanol eller blandinger herav.
Fortrinnsvis gjennomføres joderingen ved temperaturer fra
-5°C til +20°C.
Ifølge oppfinnelsen omsettes 1 mol propargyleter med den generelle formel III med ca. 1 til 0,5 mol joderingsmiddel, fortrinnsvis 1 til 1,2 mol joderingsmiddel.
De respektiv gunstigste mengder av baser og oppløsnings- og/ eller fortynningsmiddel lar seg lett fastslå ved forforsøk. Vanligvis anvender man ca. 1 til 3, fortrinnsvis 1,5 til 2 mol base pr. mol propargyleter med den generelle formel III og de samme til femganger, fortrinnsvis dobbelt til treganger vektsmengde av oppløsnings- og/eller fortynningsmiddel.
De til fremstilling av de nye jodpropargyletere med den gener elle formel I anvendbar propargyleter med den generelle formel III er delvis kjent (sml. US-patent 32 90 388).
De kan fremstilles analogt i de der omtalte fremgangsmåter, idet de tilsvarende hydroksyforbindelser med den generelle formel
hvori
A betyr oksygen, eller en metylengruppe,
R^"betyr hydrogen eller lavere alkyl,
2 3
R og R er like eller forskjellige og betyr hydrogen, laverealkyl, alkényl, eller eventuelt med halogen substituert fenyl, eller sammen danner en karbocyklisk ring med 4 til 7 karbonatomer,
1 og m betyr 0, 1 eller 2,
n betyr et helt.tall fra 0 til 4 med den forholdsregel at når 1=0, betyr n 1, 2, 3 eller 4, og
k betyr 0 eller 1,
omsettes med propargylhalogenider i nærvær av baser og i nærvær av oppløsnings- og/eller fortynningsmidler, ved temperaturer fra ca. 0 til 100°C.
Som baser egner det seg for omsetningen spesielt sterke baser, som natriumhydrid, natriumamid og/eller kalium-tert.-butylat.
Som propargylhalogenider skal det nevnes: Propargylklorid
og propargylbromid, fortrinnsvis propargylklorid.
Som oppløsningsmiddel kan det anvendes slike oppløsningsmidler som er inerte og for de anvendte baser, eksempelvis kommer det på tale dimetylformamid, tetrahydrofuran, dimetoksyetan, og/eller toluen.
Omsetningen av hydroksyforbindelser med formel IV gjennomføres hensiktsmessig således at man i første rekke gjennomfører deprotonering med basen, nemlig således at man først arbeider ved lave reaksjonstemperaturer, (ca. 0 til 20°C) og deretter fører reaksjonen til avslutning ved oppvarming til temperaturer på ca. 20 til 60°C.
Etter foretatt deprotonering tilsettes det tilsvarende pro-pargylhalogenid. Den for eterdannelsen nødvendige reaksjons-temperatur avhenger vanligvis av reaktiviteten av alkoholat og forbindelse IV, og ligger vanligvis ved ca. 20 til 100°C, fortrinnsvis 20 til 60°C. Skulle det bli nødvendig, kan temperaturen dessuten økes under omsetning.
Videre kan det være fordelaktig å gjennomføre omsetningen av hydroksyforbindelsen med formel IV med en base og et propar-gylhalogenid i vandig-organisk tofasesystem under fasetrans-ferkatalyse. Det er da mulig å anvende natriumhydroksyd som base. Egnede organiske oppløsningsmidler for fasetransfer-reaksjon, er eksempelvis diklormetan, tetrahydrofuran, og/ eller toluen. Som fasetransferkatalysatorer kan det anvendes de kjente tetraalkylammoniumsalter, som trietylbenzylammonium-klorid, tetrabutylammoniumbromid og dimetyldodecylbenzylammo-niumklorid eller kroneetere som 18-krone-6- og dibenzo-18- krone-6, sml. Dehmlow og Dehmlow, Phase Transfer Catalysis, Weinheim 1983) .
Den anvendte mengde av baser, hydroksyforbindelse med formel IV og propargylhalogenider kan igjen lett fastslås ved for-for søk .
Hydroksyforbindelsene med den generelle formel IV er delvis litteraturkjente. Når A er lik oksygen og k = 1, kan de fremstilles analogt den i Organic Syntheses Coll. Vol. 3, side 502 omtalte fremgangsmåter idet i trihydroksyforbindelser med formel
hvori
R"'", 1, m og n har den ovenfor nevnte betydning,
kondenseres under vannavspaltning med karbonylforbindelse med formel
hvori
R*•? 4 og R 3 har overnevnte betydning.
Omsetter man eksempelvis glycerol med karbonylforbindelser, så kan alt etter type av karbonylforbindelsen oppstå i okso-laner (VII) eller dioksaner (VIII) (se følgende formelskjema)
2 3
HO-CH2-CH(OH)-CH2-OH + R -CO-R
Ved denne omsetning får man under tiden blandinger hvorfra de rene forbindelser VII og VIII kan isoleres etter kjente skillemetoder, f. eks. destillering, eller kromatografi.
Det kan også være hensiktsmessig å anvende blandingen i de ytterligere syntesetrinn hvorved man endelig får en blanding av nye jodpropargyletere ifølge oppfinnelsen.
Jcdpropargyleterene ifølge oppfinnelsen med formel
kan danne stereoisomere. Således er det med en stjerne karakteriserte karbonatomer chiralt, når 1 er ulik m, eller A er ulik oksygen. Når i disse tilfeller i tillegg R<2>
er forskjellig fra R 3, er også det med to stjerner karakter-
iserte karbonatomer chiralt. Imidlertid også når de karakteriserte karbonatomer ikke er chirale, kan det dannes cis/ trans-isomere med hensyn til ringsystemet nemlig nar R 2 er forskjellig fra R 3.
De mulige enantiomere, diastereomere og cis/trans-isomere av jodpropargyletere ifølge oppfinnelsen, kan skilles ved kjente metoder, eksempelvis ved krystallisering, destillering eller omsetning med chirale hjelpereagenser (sml. E. Eliel, Stereo-chemie der Kohlenstoffverbindungen, Weinheim 1966).
Ofte skulle det imidlertid være hensiktsmessig å se bort fra adskillelse og anvende isomerblandingen.-
Oppfinnelsen omfatter såvel de rene isomere som også deres blandinger.
De nye jodpropargyletere ifølge oppfinnelsen kan anvendes
som virksomme stoffer til bekjempelse av mikroorganismer, spesielt til beskyttelse av tekniske materialer.
Tekniske materialer er ifølge oppfinnelsen ikke levende materialer som er blitt tilberedt for anvendelse i teknikken. Eksempelvis kan tekniske materialer som skal beskyttes med
de virksomme stoffer ifølge oppfinnelsen mot mirkobiell endring eller ødeleggelse være klebestoffer, lim, papir og kartong, tekstiler, lær, tre, påstrykningsmidler og kunststoff-artikler, kjølesmørestoffer og andre materialer som kan an-gripes eller spaltes av mikroorganismer. Innen rammen av materialer som skal beskyttes skal det også nevnes deler av produksjonsanlegg, eksempelvis kjølevannkretsløp som kan på-virkes ved formering av mikroorganismer. Ifølge oppfinnelsen skal det som teknisk materiale fortrinnsvis nevnes klebestoffer, lim, papir, kartong, lær, tre, påstrykningsmiddel, kjøle-smøremidler og kjølekretsløp.
Som mikroorganismer som kan bevirke en avbygning eller en
endring av de tekniske materialer, skal det eksempelvis nevnes bakterier, sopp, gjær, alger og slimorganismer. Fortrinnsvis virker de virksomme stoffer ifølge oppfinnelsen mot sopp, spesielt muggsopp, tremisfarvede og treødeleggende sopp, (Basidiomyceter), samt slimorganismer og alger.
Det skal eksempelvis nevnes mikroorganismer av følgende slekter:
Alternaria som Alternaria tenuis,
Aspergillus, som Aspergillus niger,
Chaetomium, som Chaetomium globosum,
Coniophora, som Coniophora puteana,
Lentinus, som Lentinus tigrinus,
Penicillium, som Penicillium glaucum,
Polyporus, som Polyporus versicolor,
Aureobasidium, som Aureobasidium pullulans,
Sclerophoma, som Sclerophoma pityophila,
Trichoderma, som Trichoderma viride,
Escherichia, som Escherichia coli,
Pseudomonas, som Pseudomonas aerogionosa,
Staphylococcus, som Staphylococcus aureus.
Alt etter anvendelsesområdet kan et virksomt stoff ifølge oppfinnelsen overføres i vanlige formuleringer, som oppløs-ninger, emulsjoner, suspensjoner, pulvere, pastaer og granu-later.
Disse kan fremstilles på i og for seg kjent måte, f. eks.
ved sammenblanding av de virksomme stoffer med et drøye-middel som består av flytende oppløsningsmidler og/eller faste bærestoffer, eventuelt under anvendelse av overflate-atkive midler som emulgatorer og/eller dispergeringsmidler, idet eventuelt i tilfelle anvendelse av vann som drøyemiddel anvendes organiske oppløsningsmidler som alkoholer som hjelpe-midler .
Flytende oppløsningsmidler for de virksomme stoffer kan eksempelvis være vann, alkoholer som laverealifatiske alkoholer, fortrinnsvis etanol eller isopropanol, eller benzyl-alkohol, ketoner som aceton eller metyletylketon, flytende hydrokarboner som benzylfraksjoner, halogenerte hydrokarboner, som 1,2-dikloretan.
Mikrobizide midler inneholder de virksomme stoffer vanligvis i en mengde på 1 til 95 %, fortrinnsvis på 10 til 75 %.
Anvendelseskonsentrasjonen av de virksomme stoffer ifølge oppfinnelsen retter seg etter type og forekomst av mikro-organismene som skal bekjempes, samt etter sammensetningen av materialet som skal beskyttes. Den optimale anvendte mengde kan fastslås ved prøverekker. Vanligvis ligger anvendelses-konsentras jonen i området fra 0,001 til 5 vekt-%, fortrinnsvis fra 0,05 til 1,0 vekt-%, referert til material som skal beskyttes.
De virksomme stoffer ifølge oppfinnelsen kan også foreligge
i blandinger med andre kjente virksomme stoffer. Eksempelvis skal det nevnes følgende virksomme stoffer: Benzylalko-hol, mono(poly)hemiformal og andre formaldehydavspaltende forbindelser, benzimidazolyl-metylkarbamater, tetrametyltiuram-disulfid, sinksalter av dialkylditiokarbamater, 2,4,5,6-tetra-klorisoftalonitril, tiazolylbenzimidazol, merkaptobenztia-zol, organo-tinnforbindelser, metylenbistiocyanat, fenol-derivater som 2-fenylfenol, (2,2'-dihydroksy-5,5'-diklor)-difenylmetan og 3-metyl-4-klor-fenol.
Fremstillingseksempler
A) Fremstilling av dioksalaner og dioksaner
1 mol av det tilsvarende trihydroksyforbindelse, 1 til 4
mol av den tilsvarende karbonylforbindelse, 300 ml petrol-eter og 3 g p-toluensulfonsyre, ble oppvarmet under vannut-
skiller til avslutning av vanndannelsen. Man tilsatte 3 g natriumacetat, omrørte i 30 minutter, filtrerte, -inndampet og destillerte.
Således ble det dannet:
B) Fremstilling av propargyleter.
a) 1,05 mol natriumhydrid ble suspendert i dimetylformamid og tildryppet 1 mol hydroksyforbindelse. Man lar det om-røre til avslutning av hydrogenutviklingen. Deretter til-drypper man 1,1 mol klorpropin, og etter-rører inntil reaksjonen er. fullstendig avsluttet. Man filtrerte, inndampet og destillerte.
Således ble det dannet:
b) 0,5 mol hydroksyforbindelse, 0,55 mol klorpropin, 0,025 mol tetrabutylammoniumbromid, 150 ml toluen og 250
ml 50 % NaOH omrøres først 1 time ved 20°C og deretter 1,5 time ved 60°C. Den organiske fase ble adskilt og inndampet. Residuet kunne anvendes i joderingen uten videre rensning.
Således ble det oppnådd:
c) Fremstilling av jodpropargyletere.
1 mol propargyleter oppløst i metanol avkjølt til 0°C.
Man tilsatte 1,5 mol vandig natronlut og 1,1 mol jod, og etteromrørte ved 0°C. Etter avsluttet jodering, inndampes reaksjonsblandingen, blandes med vann, avfarves med natrium-tiosulfat, opptas i diklormetan og inndampes. Produktene ble isolert generelt som olje, i noen tilfeller inntrådte krystallisering.
Således ble det oppnådd:
(1H-NMR-data: oppløsningsmiddel CDC13, TMS som indre standard).
Anvendelseseksémpel
Som sammenligningsstoff tjener 1-(jodpropargyloksy)-propan-2,3-diol (DE-OS 3 304 899).
Eksempel 1
Til påvisning av virkningen mot sopp, bestemmes den minimale hemmekonsentrasjon (MHK) av virksomme stoffer ifølge oppfinnelsen:
En agar, som fremstilles av ølvørter og pepton blandes med virksomme stoffer ifølge oppfinnelsen i konsentrasjoner fra 0,01 mg/liter til 5000 mg/liter. Etter agarens stivning foregikk kontaminasjon med renkulturer av de i tabellen opp-førte prøveorganismer. Etter 2 ukers lagring ved 28°C og 60 til 70 % relativ luftfuktighet, bestemmes MHK. MHK er den laveste konsentrasjonen av virksomt stoff, hvor det ikke foregår vekst ved hjelp av de anvendte mikr.obetyper, den er angitt i nedenstående tabell.
Eksempel 2
Virkning mot bakterier.
En agar, som som næringsmedium inneholder buljong blandes med virksomme stoffer ifølge oppfinnelsen i konsentrasjoner' fra 1 til 5000 ppm. Derpå infiseres næringsmediet resp. med de i tabell II oppførte prøveorganismer, og det infi-serte medium holdes 2 uker ved 28°C og 60 til 70 % relativ luftfuktighet. MHK er den laveste konsentrasjon . av virksomt stoff hvor det ikke foregår noe vekst ved de anvendte mikrobetyper. MHK-verdiene er gjengitt i tabell II.
Eksempel 3
(Virkning mot slimorganismer).
Stoffene ifølge oppfinnelsen 'bringes til anvendelse i konsentrasjoner på resp. 0,1 til 100 mg/liter i Allens nærings-oppløsning (Arch. Mikrobiol. 17, 34 til 53 (1952)), som i 4 liter sterilt vann inneholder 0,2 g ammoniumklorid, 4,0 g natriumnitrat, 1,0 g dikaliumhydrogenfosfat, 0,2 g kalsium-klorid, 2,05 g magnesiumsulfat, 0,02 g jernklorid og 1 % kaprolaktam oppløst i litt aceton. Kort på forhånd infiseres næringsoppløsningen med slimorganismer (ca. 10^ kimer/ ml), som ble isolert fra ved polyamidfremstilling anvendt spinnvann-kretsløp. Næringsoppløsningené som har den minimale hemmekonsentrasjon (MHK) eller større virksomme stoffkonsen-trasjoner, er ennå helt klare etter 3 ukers kulturer ved værelsestemperatur, dvs. den i virksomt stoff-frie nærings-oppløsninger etter 3 til 4 dager merkbare sterke formering av mikrobene og slimdannelse uteblir.
Tabell III
MHK-verdier i mg/l ved innvirkning av de nedenfor angitte stoffer på slimorganismer
Eksempel 4
En blandingskultur av grønn-, blå-, brun- og kiselalger (Stichococcus bacillaris Naegeli, Euglena gracilis, Klebs, Chlorella pyrenoidosa Chick, Phormidium foveolarum Gomont, Oscillatoria geminata Meneghini og Phaeodactylum tricornu-tum Bohlin) haes under gjennombobling av luft i Allens nær-ingsoppløsning (arkiv Mikrobiologi 17, 34-53 (1952)), som på 4 liter sterilt vann inneholder 0,2 g ammoniumklorid, 4,0 g natriumnitrat, 5,0 g dikaliumhydrogenfosfat, 0,2 g kalsium-klorid, 2,05 g magnesiumsulfat og 0,02 g jernklorid. Etter 2 uker er næringsoppløsningen på grunn av intens algevekst farvet mørkegrønn-blå. Utrydning av algene etter tilsetning av virksomme stoffer ifølge oppfinnelsen ser man på avfarv-ningen av næringsoppløsningen.
Tabell IV
Alge-utryddende konsentrasjon (mg/l) av de nedenfor angitte stoffer:
Claims (6)
1. Nye jodpropargyletere med formel
hvori
A betyr oksygen eller en metylengruppe,
R^" betyr hydrogen eller lavere alkyl,
2 3
R og R er like eller forskjellige og betyr hydrogen,
laverealkyl, alkenyl eller eventuelt med halogen substituert fenyl, eller sammen danner en karbocyklisk ring med 4 til 7 karbonatomer,
1 og m betyr 0, 1 eller 2,
n betyr et helt tall fra 0 til 4, med den forholdsregel at
når 1 = o, betyr ni, 2, 3 og 4, og
k betyr 0 eller 1.
2. Fremgangsmåte til fremstilling av nye jodpropargyletere med formel
hvori
A betyr oksygen eller en metylengruppe,
R betyr hydrogen eller lavere alkyl,
R 2 og R 3 er like eller forskjellige og betyr hydrogen,
lavere alkyl, alkenyl eller eventuelt med halogen substituert fenyl, eller sammen danner en karbocyklisk ring med 4 til 7 karbonatomer,
1 og m betyr 0, 1 eller 2,
n betyr et helt tall fra 0 til 4 med den forholdsregel at
når 1=0, betyr ni, 2, 3 og 4, og
k betyr 0 eller 1,
karakterisert ved at propargyletere med formel
hvori
12 3
A, R , R , R , 1, m, n og k har overnevnte betydning, omsettes joderingsmidler i nærvær av oppløsnings- og/eller fortynningsmidler og i nærvær av baser ved temperaturer fra -10 til 30°C.
3. Mikrobizid middel inneholder de nye jodpropargyletere med formel
hvori
A betyr oksygen eller en metylengruppe, R <1> betyr hydrogen eller lavere alkyl,
2 3
R og R er like eller forskjellige og betyr hydrogen,
lavere alkyl, alkenyl eller eventuelt med halogen substituert fenyl, eller sammen danner en karbocyklisk ring med 4 til 7 karbonatomer,
1 og m betyr 0, 1 eller 2,
n betyr et helt tall fra 0 til 4 med den forholdsregel
når 1=0, betyr ni, 2, 3 og 4, og
k betyr 0 eller 1.
4. Mikrobizid middel ifølge krav 3 inneholdende 1 til 95 vekt-% av det nye jodpropargyleter.
5. Anvendelse av mikrobizide midler ifølge krav 3 og 4,
til bekjempelse av tekniske materialer.
6. Anvendelse ifølge krav 5, til beskyttelse av tre mot tre-misfarvende og treødeleggende sopp.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19853510203 DE3510203A1 (de) | 1985-03-21 | 1985-03-21 | Neue iodpropargylether, ein verfahren zu ihrer herstellung und ihre verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
NO860844L true NO860844L (no) | 1986-09-22 |
Family
ID=6265888
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO860844A NO860844L (no) | 1985-03-21 | 1986-03-06 | Nye jodpropargyletere, en fremgangsmaate til deres fremstilling og deres anvendelse. |
Country Status (9)
Country | Link |
---|---|
US (2) | US4719227A (no) |
EP (1) | EP0199047B1 (no) |
JP (1) | JPH0629279B2 (no) |
CA (1) | CA1326038C (no) |
DE (2) | DE3510203A1 (no) |
DK (1) | DK129386A (no) |
FI (1) | FI861153A (no) |
NO (1) | NO860844L (no) |
ZA (1) | ZA862075B (no) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2054221C (en) * | 1990-10-31 | 1999-09-14 | David Oppong | Synergistic combinations of iodopropargyl compounds with hexahydro-1,3,5-tris(2-hydroxyethyl)-s-triazine in controlling fungal and bacterial growth in aqueous fluids |
ZA926535B (en) | 1991-11-07 | 1994-09-30 | Buckman Laboraties Internation | Synergistic combinations of iodopropargyl compounds with 1,2-benzisothiazolin-3-one in controlling fungal and bacterial growth in aqueous fluids |
DE4141953A1 (de) * | 1991-12-19 | 1993-06-24 | Bayer Ag | Mikrobizide mittel |
DE4217523A1 (de) * | 1992-05-27 | 1993-12-02 | Bayer Ag | Mittel zum Schutz von Schnittholz |
US5707929A (en) * | 1995-05-08 | 1998-01-13 | Troy Chemical Corporation | Biocidal compositions comprising mixtures of haloproynyl compounds and sulfur containing triazines |
US6017955A (en) * | 1995-06-07 | 2000-01-25 | Troy Technology Corporation, Inc. | Method of stabilizing biocidal compositions of haloalkynyl compounds |
US5906981A (en) * | 1996-06-04 | 1999-05-25 | Troy Corporation | Halopropargyl inclusion complexes |
US6059991A (en) | 1997-12-12 | 2000-05-09 | Troy Technology Corporation, Inc. | Stabilized composition containing halopropynyl compounds |
US5938825A (en) * | 1998-05-21 | 1999-08-17 | Troy Technology Corporation Inc. | Stabilized antimicrobial compositions containing halopropynyl compounds |
US6140370A (en) * | 1998-09-21 | 2000-10-31 | Troy Technology Corporation, Inc. | Stabilized alkyd based compositions containing halopropynl compounds |
US6197805B1 (en) | 1999-05-27 | 2001-03-06 | Troy Technology Corporation, Inc. | Broad spectrum antimicrobial mixtures |
US6472424B1 (en) | 2000-06-07 | 2002-10-29 | Troy Technology Corporation, Inc. | Stabilized antimicrobial compositions containing halopropynyl compounds and benzylidene camphors |
DE60234057D1 (de) | 2001-07-25 | 2009-11-26 | Raptor Pharmaceutical Inc | Zusammensetzungen und verfahren zur modulation des transports durch die blut-hirn-schranke |
CA2535729A1 (en) * | 2003-07-30 | 2005-02-10 | Triosyn Holding, Inc. | Method and system for control of microorganisms in metalworking fluid |
CA2539185A1 (en) * | 2003-09-19 | 2005-03-31 | Arch Chemicals, Inc. | Stabilized halopropynyl compositions as preservatives |
CN103259027A (zh) | 2005-04-28 | 2013-08-21 | 普罗透斯数字保健公司 | 药物信息*** |
EP2063905B1 (en) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
MY142639A (en) * | 2007-11-21 | 2010-12-15 | Mimos Berhad | Immobilized nitrate ionophore |
GB2459691B (en) * | 2008-04-30 | 2013-05-22 | Arch Timber Protection Ltd | Formulations |
PL3395372T3 (pl) | 2009-02-20 | 2022-07-25 | EnhanX Biopharm Inc. | Układ do dostarczania leków na bazie glutationu |
KR20190116576A (ko) | 2009-05-06 | 2019-10-14 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
KR20220044326A (ko) | 2019-08-09 | 2022-04-07 | 트로이 코포레이션 | 폴리머 베타인 및 카바메이트를 포함하는 상승작용적 목재 보존 조성물 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3290388A (en) * | 1963-07-03 | 1966-12-06 | Dow Chemical Co | Monopropynyl ethers of glycerol |
US3700698A (en) * | 1971-05-12 | 1972-10-24 | Hoffmann La Roche | 1,2-epoxy-3-(3-iodo-2-propynyloxy)-propane |
US4338327A (en) * | 1978-10-06 | 1982-07-06 | Janssen Pharmaceutica, N.V. | Substituted 1-(2-aryl-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazoles |
DE3304899A1 (de) * | 1983-02-12 | 1984-08-16 | Henkel KGaA, 4000 Düsseldorf | Substituierte 1-(3-iod-2-propinyloxy-)-2bzw.3-propanole, ihre herstellung und ihre verwendung als antimikrobielle substanzen |
-
1985
- 1985-03-21 DE DE19853510203 patent/DE3510203A1/de not_active Withdrawn
-
1986
- 1986-02-27 US US06/834,287 patent/US4719227A/en not_active Expired - Fee Related
- 1986-03-06 NO NO860844A patent/NO860844L/no unknown
- 1986-03-10 DE DE8686103196T patent/DE3660869D1/de not_active Expired
- 1986-03-10 EP EP86103196A patent/EP0199047B1/de not_active Expired
- 1986-03-19 FI FI861153A patent/FI861153A/fi not_active Application Discontinuation
- 1986-03-19 CA CA000504515A patent/CA1326038C/en not_active Expired - Fee Related
- 1986-03-20 ZA ZA862075A patent/ZA862075B/xx unknown
- 1986-03-20 JP JP61061054A patent/JPH0629279B2/ja not_active Expired - Lifetime
- 1986-03-20 DK DK129386A patent/DK129386A/da not_active IP Right Cessation
-
1987
- 1987-06-26 US US07/067,674 patent/US4855318A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JPS61227577A (ja) | 1986-10-09 |
JPH0629279B2 (ja) | 1994-04-20 |
US4855318A (en) | 1989-08-08 |
EP0199047A3 (en) | 1987-04-15 |
DK129386D0 (da) | 1986-03-20 |
EP0199047B1 (de) | 1988-10-05 |
DE3510203A1 (de) | 1986-09-25 |
FI861153A (fi) | 1986-09-22 |
CA1326038C (en) | 1994-01-11 |
EP0199047A2 (de) | 1986-10-29 |
FI861153A0 (fi) | 1986-03-19 |
DK129386A (da) | 1986-09-22 |
ZA862075B (en) | 1986-11-26 |
US4719227A (en) | 1988-01-12 |
DE3660869D1 (en) | 1988-11-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO860844L (no) | Nye jodpropargyletere, en fremgangsmaate til deres fremstilling og deres anvendelse. | |
EP0378953B1 (fr) | Benzylidène azolylméthylecycloalcane et utilisation comme fongicide | |
EP0258161A2 (fr) | Dérivés de 2,5-dihydrofuranne à groupe triazole ou imidazole, procédé de préparation, utilisation comme fongicide | |
EP0212281A1 (de) | 1-Heteroaryl-4-aryl-pyrazol-Derivate | |
EP0151084A2 (fr) | Fongicides à groupes triazole et oligoéther | |
IE43662B1 (en) | 3-alkoxy-benzo-1,2,4-triazines, process for their preparation and their use as fungicides and bactericides | |
CA1283118C (en) | Hydroxypyrazole derivatives, their preparation and their use against microorganisms | |
EP0254866A1 (de) | Chinolinderivate, Verfahren zu ihrer Herstellung, diese enthaltende Mikrobizide und ihre Verwendung zur Bekämpfung von Bakterien und Pilzen | |
PT87764B (pt) | Processo para a preparacao de eteres (azolil-vinil)-fenol-alcenilicos com efeito microbicida | |
EP0246982B1 (fr) | Composés à groupements triazole ou imidazole et tétrahydrofurane utilisation de cuex-ci à titre de fongicides et procédés de préparation | |
US4661632A (en) | Halogenopropargylformamide pesticides | |
US4575517A (en) | Microbicidal agent for preserving industrial materials | |
US3873703A (en) | Bactericidal and fungicidal compositions and methods of killing bacteria and fungi using 8-oxyguinoline-and 8-oxyguinaldine acrylates | |
FR2622582A1 (fr) | Composes a groupe imidazole ou triazole, utilisation de ceux-ci a titre de fongicide, procede de preparation | |
US4198428A (en) | Aryl-thiocarboxylic acid thiocyanomethyl esters | |
DE69124482T2 (de) | Azolylmethyloxabicyclohexane Derivate, ihre Zwischenprodukte und fungizide Zusammensetzungen | |
US5177090A (en) | Microbicidal agents | |
US4778511A (en) | Fluorine-containing N-sulphenylated indazoles for use as bactericides and fungicides | |
US4879310A (en) | New cyanohydrin iodopropargyl ethers, process for their preparation and their use as microbicides | |
FR2499077A1 (fr) | Derives de l'aniline, leur preparation et produits microbicides en contenant | |
DE3408879A1 (de) | Pyridiniumsalze und diese enthaltende fungizide und bakterizide | |
DE69619181T2 (de) | Verbindungen mit antimikrobieller Breitspektrum-Wirkung | |
EP0094562A1 (de) | Diaminderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
LU83749A1 (fr) | Nouveaux derives de la dihydro-2,3 pyrone-4,leur preparation,les compositions herbicides les contenant et leur utilisation pour le desherbage selectif des cultures | |
JPH0373538B2 (no) |