JPS62881B2 - - Google Patents

Info

Publication number: JPS62881B2
Authority: JP; Japan
Prior art keywords: group; iodo; propyne; compound; substituent
Prior art date: 1978-03-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP2956478A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54122727A (en

Inventor

Yasuhiro Morisawa

Seiji Konishi

Mitsuru Kataoka

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-03-15

Filing date

1978-03-15

Publication date

1987-01-10

1978-03-15 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1978-03-15 Priority to JP2956478A priority Critical patent/JPS54122727A/ja

1979-03-13 Priority to US06/020,165 priority patent/US4259350A/en

1979-03-13 Priority to CA000323296A priority patent/CA1116622A/fr

1979-03-14 Priority to NO790865A priority patent/NO151703C/no

1979-03-14 Priority to SE7902291A priority patent/SE445344B/sv

1979-03-15 Priority to FR7906615A priority patent/FR2465415A1/fr

1979-03-15 Priority to DE19792910220 priority patent/DE2910220A1/de

1979-03-15 Priority to GB7909082A priority patent/GB2016457B/en

1979-09-22 Publication of JPS54122727A publication Critical patent/JPS54122727A/ja

1987-01-10 Publication of JPS62881B2 publication Critical patent/JPS62881B2/ja

Status Granted legal-status Critical Current

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
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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

Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP2956478A 1978-03-15 1978-03-15 Fungicidal, antiseptic, anti-termitic agent Granted JPS54122727A (en)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
JP2956478A JPS54122727A (en)	1978-03-15	1978-03-15	Fungicidal, antiseptic, anti-termitic agent
US06/020,165 US4259350A (en)	1978-03-15	1979-03-13	Iodopropargyl derivatives, their use and preparation
CA000323296A CA1116622A (fr)	1978-03-15	1979-03-13	Derives de l'iodopropargyle, leur utilisation et leur 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
FR7906615A FR2465415A1 (fr)	1978-03-15	1979-03-15	Derives iodopropargyliques et leur application a la conservation de matieres organiques
DE19792910220 DE2910220A1 (de)	1978-03-15	1979-03-15	Jodpropargylderivate und ihre verwendung als konservierungsmittel von abbaubaren organischen materialien
GB7909082A GB2016457B (en)	1978-03-15	1979-03-15	Iodopropargyl derivatives their use and preparation

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 (fr)	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 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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
CN104409766B (zh) *	2010-02-03	2017-04-12	宇部兴产株式会社	非水电解液、使用其的电化学元件以及非水电解液中使用的炔基化合物

1978
- 1978-03-15 JP JP2956478A patent/JPS54122727A/ja active Granted

Also Published As

Publication number	Publication date
JPS54122727A (en)	1979-09-22

Publication	Publication Date	Title
US4259350A (en)	1981-03-31	Iodopropargyl derivatives, their use and preparation
JP2761441B2 (ja)	1998-06-04	木材保存性オキサチアジン化合物
US6827949B2 (en)	2004-12-07	Wood preservative
JPS635361B2 (fr)	1988-02-03
JPS62881B2 (fr)	1987-01-10
TW521993B (en)	2003-03-01	Pesticidal compositions
US4487781A (en)	1984-12-11	Trihaloallyl derivatives having anti-fungal activities
JPS6340402B2 (fr)	1988-08-11
JPS6215054B2 (fr)	1987-04-06
JPH0112747B2 (fr)	1989-03-02
JPS632419B2 (fr)	1988-01-19
JPS6364415B2 (fr)	1988-12-12
EP1112688B1 (fr)	2004-09-22	Methode de lutte contre les termites
JPS6059898B2 (ja)	1985-12-27	ヨ−ドプロパルギル誘導体、およびヨ−ドプロパルギル誘導体を有効成分とする防カビ、防腐、防蟻剤
EP0040344B1 (fr)	1984-12-05	Dérivé de l'acide benzène sulphénique 4-nitro-2-trichlorométhyle, procédé de fabrication et fongicides le contenant
JPS6250460B2 (fr)	1987-10-24
JPS6366820B2 (fr)	1988-12-22
SU346834A1 (fr)
EP0755927B1 (fr)	2001-07-18	Derive de dimethylfurancarboxanilide
WO1997006676A1 (fr)	1997-02-27	Formulations d'agents microbicides
JPS5952043B2 (ja)	1984-12-18	木材用防腐防カビ剤
JPS6341375B2 (fr)	1988-08-17
JPH08231312A (ja)	1996-09-10	工業用防腐防かび剤
JPH0224201B2 (fr)	1990-05-28