JPS62881B2 - - Google Patents
Info
- Publication number
- JPS62881B2 JPS62881B2 JP2956478A JP2956478A JPS62881B2 JP S62881 B2 JPS62881 B2 JP S62881B2 JP 2956478 A JP2956478 A JP 2956478A JP 2956478 A JP2956478 A JP 2956478A JP S62881 B2 JPS62881 B2 JP S62881B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- iodo
- propyne
- compound
- substituent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 cyanoacetyl group Chemical group 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 29
- 230000000843 anti-fungal effect Effects 0.000 claims description 14
- 229940121375 antifungal agent Drugs 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000002424 termiticide Substances 0.000 claims description 8
- 230000002421 anti-septic effect Effects 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000002023 wood Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 239000003755 preservative agent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000002335 preservative effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GILKVTZWTVOGJV-UHFFFAOYSA-N 1-iodoprop-2-yn-1-ol Chemical compound OC(I)C#C GILKVTZWTVOGJV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000256602 Isoptera Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000077 insect repellent Substances 0.000 description 3
- 238000002372 labelling Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- DAQOCQOTMNGLSN-UHFFFAOYSA-N 3-iodoprop-2-ynyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC#CI DAQOCQOTMNGLSN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241001149956 Cladosporium herbarum Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000010998 test method Methods 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
- 239000004563 wettable powder Substances 0.000 description 2
- 239000003171 wood protecting agent Substances 0.000 description 2
- MKNJWAXSYGAMGJ-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl MKNJWAXSYGAMGJ-UHFFFAOYSA-N 0.000 description 1
- COPHGKSLUXDLPA-HZJYTTRNSA-N (6z,9z)-18-(3-iodoprop-2-ynoxy)octadeca-6,9-diene Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCOCC#CI COPHGKSLUXDLPA-HZJYTTRNSA-N 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- MFPWUQYUEBRWLS-UHFFFAOYSA-N 2-ethylhexyl 3-iodoprop-2-ynyl carbonate Chemical compound CCCCC(CC)COC(=O)OCC#CI MFPWUQYUEBRWLS-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 1
- QQFMWGWROGCSNW-WJPDYIDTSA-N 3-iodoprop-2-ynyl (2e,4e)-hexa-2,4-dienoate Chemical compound C\C=C\C=C\C(=O)OCC#CI QQFMWGWROGCSNW-WJPDYIDTSA-N 0.000 description 1
- NUNDLMBNWYIXCW-DUXPYHPUSA-N 3-iodoprop-2-ynyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OCC#CI NUNDLMBNWYIXCW-DUXPYHPUSA-N 0.000 description 1
- PCUOYXVUFHFSTI-UHFFFAOYSA-N 3-iodoprop-2-ynyl 11-bromoundecanoate Chemical compound BrCCCCCCCCCCC(=O)OCC#CI PCUOYXVUFHFSTI-UHFFFAOYSA-N 0.000 description 1
- XVNRVHKJHIVPNJ-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OCC#CI XVNRVHKJHIVPNJ-UHFFFAOYSA-N 0.000 description 1
- SCAVQVOJFSOTKP-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC#CI SCAVQVOJFSOTKP-UHFFFAOYSA-N 0.000 description 1
- CPLAFHFBEDCJCX-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2,5-dichlorobenzenesulfonate Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)OCC#CI)=C1 CPLAFHFBEDCJCX-UHFFFAOYSA-N 0.000 description 1
- RYJOHJSQIKFRAV-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-(2,4-dichlorophenoxy)acetate Chemical compound ClC1=CC=C(OCC(=O)OCC#CI)C(Cl)=C1 RYJOHJSQIKFRAV-UHFFFAOYSA-N 0.000 description 1
- KVUKOHXJQPLRFM-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-(4-chlorophenoxy)acetate Chemical compound ClC1=CC=C(OCC(=O)OCC#CI)C=C1 KVUKOHXJQPLRFM-UHFFFAOYSA-N 0.000 description 1
- KKMLNGKLUIUFTO-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-bromo-3-methylbutanoate Chemical compound CC(C)C(Br)C(=O)OCC#CI KKMLNGKLUIUFTO-UHFFFAOYSA-N 0.000 description 1
- CAAVEFWIUNFDLK-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-bromoacetate Chemical compound BrCC(=O)OCC#CI CAAVEFWIUNFDLK-UHFFFAOYSA-N 0.000 description 1
- KZJWHZKDQSYZSK-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-bromobenzoate Chemical compound BrC1=CC=CC=C1C(=O)OCC#CI KZJWHZKDQSYZSK-UHFFFAOYSA-N 0.000 description 1
- AHFXMZNCWCCPSU-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OCC#CI AHFXMZNCWCCPSU-UHFFFAOYSA-N 0.000 description 1
- QCDPMXWAEFHQIW-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC#CI QCDPMXWAEFHQIW-UHFFFAOYSA-N 0.000 description 1
- JEROFKVRISJUAV-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-chloroacetate Chemical compound ClCC(=O)OCC#CI JEROFKVRISJUAV-UHFFFAOYSA-N 0.000 description 1
- RVIFIOKPGHFMMK-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OCC#CI RVIFIOKPGHFMMK-UHFFFAOYSA-N 0.000 description 1
- RWCUPYPYNAJXTC-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-chlorobutanoate Chemical compound CCC(Cl)C(=O)OCC#CI RWCUPYPYNAJXTC-UHFFFAOYSA-N 0.000 description 1
- QRUAIVNTDCEQCY-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-cyanoacetate Chemical compound IC#CCOC(=O)CC#N QRUAIVNTDCEQCY-UHFFFAOYSA-N 0.000 description 1
- ZDXPWTMILRZACK-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OCC#CI ZDXPWTMILRZACK-UHFFFAOYSA-N 0.000 description 1
- LXTNWFDYPQODNB-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC#CI LXTNWFDYPQODNB-UHFFFAOYSA-N 0.000 description 1
- MLEDGWHOSPIKOY-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-iodobenzoate Chemical compound IC#CCOC(=O)C1=CC=CC=C1I MLEDGWHOSPIKOY-UHFFFAOYSA-N 0.000 description 1
- QSVRSZNMUGBBOL-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methoxybenzoate Chemical compound COC1=CC=CC=C1C(=O)OCC#CI QSVRSZNMUGBBOL-UHFFFAOYSA-N 0.000 description 1
- MJVYAPBQLRBBLH-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methyl-3-nitrobenzoate Chemical compound CC1=C(C(=O)OCC#CI)C=CC=C1[N+]([O-])=O MJVYAPBQLRBBLH-UHFFFAOYSA-N 0.000 description 1
- OOOCSWPNBQXCTH-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methylbenzoate Chemical compound CC1=CC=CC=C1C(=O)OCC#CI OOOCSWPNBQXCTH-UHFFFAOYSA-N 0.000 description 1
- HDDLZAKHAOXDHL-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OCC#CI HDDLZAKHAOXDHL-UHFFFAOYSA-N 0.000 description 1
- JEZHVFOATQBTHM-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methylpentanoate Chemical compound CCCC(C)C(=O)OCC#CI JEZHVFOATQBTHM-UHFFFAOYSA-N 0.000 description 1
- AUWUIAVPMYQTNH-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methylpentyl carbonate Chemical compound CCCC(C)COC(=O)OCC#CI AUWUIAVPMYQTNH-UHFFFAOYSA-N 0.000 description 1
- BMGYXLRUPUPWGT-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methylpropanoate Chemical compound CC(C)C(=O)OCC#CI BMGYXLRUPUPWGT-UHFFFAOYSA-N 0.000 description 1
- YYLVTRDYXYYKIO-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-methylpropyl carbonate Chemical compound CC(C)COC(=O)OCC#CI YYLVTRDYXYYKIO-UHFFFAOYSA-N 0.000 description 1
- PCSGXNNUSOOQMD-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-phenoxybutanoate Chemical compound IC#CCOC(=O)C(CC)OC1=CC=CC=C1 PCSGXNNUSOOQMD-UHFFFAOYSA-N 0.000 description 1
- MIVDVFNUSOHBFB-UHFFFAOYSA-N 3-iodoprop-2-ynyl 2-phenylacetate Chemical compound IC#CCOC(=O)CC1=CC=CC=C1 MIVDVFNUSOHBFB-UHFFFAOYSA-N 0.000 description 1
- XUYZPMGVYZVMCL-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3,4-dimethylbenzoate Chemical compound CC1=CC=C(C(=O)OCC#CI)C=C1C XUYZPMGVYZVMCL-UHFFFAOYSA-N 0.000 description 1
- CIGQELCSLGTLNC-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3,5,5-trimethylhexyl carbonate Chemical compound CC(C)(C)CC(C)CCOC(=O)OCC#CI CIGQELCSLGTLNC-UHFFFAOYSA-N 0.000 description 1
- DNGNJSWAEXDYAH-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-bromobenzoate Chemical compound BrC1=CC=CC(C(=O)OCC#CI)=C1 DNGNJSWAEXDYAH-UHFFFAOYSA-N 0.000 description 1
- QTZMCIFXWIPTRV-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-chlorobenzoate Chemical compound ClC1=CC=CC(C(=O)OCC#CI)=C1 QTZMCIFXWIPTRV-UHFFFAOYSA-N 0.000 description 1
- LDZOVEILPQSFLJ-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-chlorobutanoate Chemical compound CC(Cl)CC(=O)OCC#CI LDZOVEILPQSFLJ-UHFFFAOYSA-N 0.000 description 1
- ARTRMIOWYUCBNO-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-chloropropanoate Chemical compound ClCCC(=O)OCC#CI ARTRMIOWYUCBNO-UHFFFAOYSA-N 0.000 description 1
- FKQUDOZFEKFTMM-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-cyanobenzoate Chemical compound IC#CCOC(=O)C1=CC=CC(C#N)=C1 FKQUDOZFEKFTMM-UHFFFAOYSA-N 0.000 description 1
- GTIBHZMKVADBAR-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-fluorobenzoate Chemical compound FC1=CC=CC(C(=O)OCC#CI)=C1 GTIBHZMKVADBAR-UHFFFAOYSA-N 0.000 description 1
- DHBPBHDLZBTHNZ-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-methoxybenzoate Chemical compound COC1=CC=CC(C(=O)OCC#CI)=C1 DHBPBHDLZBTHNZ-UHFFFAOYSA-N 0.000 description 1
- LQTUGNHYSYMLED-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-methylbenzoate Chemical compound CC1=CC=CC(C(=O)OCC#CI)=C1 LQTUGNHYSYMLED-UHFFFAOYSA-N 0.000 description 1
- HYTHUXBBKFFFRP-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OCC#CI HYTHUXBBKFFFRP-UHFFFAOYSA-N 0.000 description 1
- RJSMBSLEYLCFEV-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-methylbutyl carbonate Chemical compound CC(C)CCOC(=O)OCC#CI RJSMBSLEYLCFEV-UHFFFAOYSA-N 0.000 description 1
- RLQHLKDJYHBMEY-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)OCC#CI)=C1 RLQHLKDJYHBMEY-UHFFFAOYSA-N 0.000 description 1
- XTEZXPFGCNTKRN-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-phenylprop-2-enoate Chemical compound IC#CCOC(=O)C=CC1=CC=CC=C1 XTEZXPFGCNTKRN-UHFFFAOYSA-N 0.000 description 1
- JIUMQBFFDMADOU-UHFFFAOYSA-N 3-iodoprop-2-ynyl 3-phenylpropanoate Chemical compound IC#CCOC(=O)CCC1=CC=CC=C1 JIUMQBFFDMADOU-UHFFFAOYSA-N 0.000 description 1
- LCVMGGPEWSDALD-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-bromobenzenesulfonate Chemical compound BrC1=CC=C(S(=O)(=O)OCC#CI)C=C1 LCVMGGPEWSDALD-UHFFFAOYSA-N 0.000 description 1
- MCGBDHZQLQTKMH-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-bromobenzoate Chemical compound BrC1=CC=C(C(=O)OCC#CI)C=C1 MCGBDHZQLQTKMH-UHFFFAOYSA-N 0.000 description 1
- DZWNLWZYIKYHOT-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-chlorobenzenesulfonate Chemical compound ClC1=CC=C(S(=O)(=O)OCC#CI)C=C1 DZWNLWZYIKYHOT-UHFFFAOYSA-N 0.000 description 1
- KOOTVSXLMXTOER-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-chlorobenzoate Chemical compound ClC1=CC=C(C(=O)OCC#CI)C=C1 KOOTVSXLMXTOER-UHFFFAOYSA-N 0.000 description 1
- BJMAIAVVPRPLKH-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-chlorobutanoate Chemical compound ClCCCC(=O)OCC#CI BJMAIAVVPRPLKH-UHFFFAOYSA-N 0.000 description 1
- XFHJSYGAWLJLIM-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-cyanobenzoate Chemical compound IC#CCOC(=O)C1=CC=C(C#N)C=C1 XFHJSYGAWLJLIM-UHFFFAOYSA-N 0.000 description 1
- SVFFHHCBSGSYFX-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-fluorobenzenesulfonate Chemical compound FC1=CC=C(S(=O)(=O)OCC#CI)C=C1 SVFFHHCBSGSYFX-UHFFFAOYSA-N 0.000 description 1
- PIIFIHSIEGGMJM-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-fluorobenzoate Chemical compound FC1=CC=C(C(=O)OCC#CI)C=C1 PIIFIHSIEGGMJM-UHFFFAOYSA-N 0.000 description 1
- GUQVULROMOPQCL-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-iodobenzoate Chemical compound IC#CCOC(=O)C1=CC=C(I)C=C1 GUQVULROMOPQCL-UHFFFAOYSA-N 0.000 description 1
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- HEFKXWFKPSYLHJ-UHFFFAOYSA-N 3-iodoprop-2-ynyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC#CI)C=C1 HEFKXWFKPSYLHJ-UHFFFAOYSA-N 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2956478A JPS54122727A (en) | 1978-03-15 | 1978-03-15 | Fungicidal, antiseptic, anti-termitic agent |
| CA000323296A CA1116622A (en) | 1978-03-15 | 1979-03-13 | Iodopropargyl derivatives their use and preparation |
| US06/020,165 US4259350A (en) | 1978-03-15 | 1979-03-13 | Iodopropargyl derivatives, their use and preparation |
| NO790865A NO151703C (no) | 1978-03-15 | 1979-03-14 | Jodpropargylestre til anvendelse i impregneringsmidler mot sopp og termitter. |
| SE7902291A SE445344B (sv) | 1978-03-15 | 1979-03-14 | Jodopropargylderivat samt dess anvendning som skyddsmedel for tre, vatmassa, papper, ark, fiber, leder, lim, ferg eller konstharts |
| GB7909082A GB2016457B (en) | 1978-03-15 | 1979-03-15 | Iodopropargyl derivatives their use and preparation |
| DE19792910220 DE2910220A1 (de) | 1978-03-15 | 1979-03-15 | Jodpropargylderivate und ihre verwendung als konservierungsmittel von abbaubaren organischen materialien |
| FR7906615A FR2465415A1 (fr) | 1978-03-15 | 1979-03-15 | Derives iodopropargyliques et leur application a la conservation de matieres organiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2956478A JPS54122727A (en) | 1978-03-15 | 1978-03-15 | Fungicidal, antiseptic, anti-termitic agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54122727A JPS54122727A (en) | 1979-09-22 |
| JPS62881B2 true JPS62881B2 (de) | 1987-01-10 |
Family
ID=12279616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2956478A Granted JPS54122727A (en) | 1978-03-15 | 1978-03-15 | Fungicidal, antiseptic, anti-termitic agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54122727A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3416772A1 (de) * | 1984-05-07 | 1985-11-07 | Consortium für elektrochemische Industrie GmbH, 8000 München | Substituierte phenylessigsaeurejodpropargylester, ihre herstellung und verwendung als biozide mittel |
| DE3614836A1 (de) * | 1986-05-02 | 1987-11-05 | Dow Chemical Co | Hydroxyphenyl- und hydroxyphenoxyalkansaeurejodpropargylester |
| KR20120124424A (ko) * | 2010-02-03 | 2012-11-13 | 우베 고산 가부시키가이샤 | 비수 전해액, 그것을 이용한 전기화학 소자, 및 그것에 이용되는 알킨일 화합물 |
-
1978
- 1978-03-15 JP JP2956478A patent/JPS54122727A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54122727A (en) | 1979-09-22 |
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