CA1124251A - Herbicidally active carbamic acid phenyl esters and their manufacture and use - Google Patents
Herbicidally active carbamic acid phenyl esters and their manufacture and useInfo
- Publication number
- CA1124251A CA1124251A CA337,402A CA337402A CA1124251A CA 1124251 A CA1124251 A CA 1124251A CA 337402 A CA337402 A CA 337402A CA 1124251 A CA1124251 A CA 1124251A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- ester
- acid
- compound
- treated
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 title claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 241000196324 Embryophyta Species 0.000 claims abstract description 20
- -1 1,3-dioxolan-2-yl-methyl Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims description 85
- 239000002253 acid Substances 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 44
- 238000011282 treatment Methods 0.000 claims description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 4
- QGHFBLVFNUYCSV-UHFFFAOYSA-N 2-methoxyethyl(phenyl)carbamic acid Chemical compound COCCN(C(O)=O)C1=CC=CC=C1 QGHFBLVFNUYCSV-UHFFFAOYSA-N 0.000 claims description 3
- OLTPKMBOLARPFC-UHFFFAOYSA-N phenyl(2-phenylethyl)carbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)CCC1=CC=CC=C1 OLTPKMBOLARPFC-UHFFFAOYSA-N 0.000 claims description 3
- ZSGBJWHPVMVFMG-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methyl-phenylcarbamic acid Chemical compound CC1(OCC(O1)CN(C(O)=O)C1=CC=CC=C1)C ZSGBJWHPVMVFMG-UHFFFAOYSA-N 0.000 claims description 2
- ZFZPIYLWLOTMSI-UHFFFAOYSA-N 2,2-dimethoxyethyl-(3-methylphenyl)carbamic acid Chemical compound COC(CN(C(O)=O)C1=CC(=CC=C1)C)OC ZFZPIYLWLOTMSI-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 244000068988 Glycine max Species 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims description 2
- 241000219146 Gossypium Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 244000061456 Solanum tuberosum Species 0.000 claims description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims 2
- ALBJOELGYPWTHY-UHFFFAOYSA-N (2-amino-2-oxoethyl)-phenylcarbamic acid Chemical compound NC(=O)CN(C(O)=O)C1=CC=CC=C1 ALBJOELGYPWTHY-UHFFFAOYSA-N 0.000 claims 1
- LSQZXJRQIWAMOR-UHFFFAOYSA-N 2-ethoxyethyl-(4-fluorophenyl)carbamic acid Chemical compound C(C)OCCN(C(O)=O)C1=CC=C(C=C1)F LSQZXJRQIWAMOR-UHFFFAOYSA-N 0.000 claims 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims 1
- 235000021536 Sugar beet Nutrition 0.000 claims 1
- AXOWRHJSTJPLJR-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] n-(2,2-dimethoxyethyl)-n-phenylcarbamate Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CC(OC)OC)C=2C=CC=CC=2)=C1 AXOWRHJSTJPLJR-UHFFFAOYSA-N 0.000 claims 1
- GHZHNWOTAAHZLZ-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] n-(cyanomethyl)-n-phenylcarbamate Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=CC=CC=2)=C1 GHZHNWOTAAHZLZ-UHFFFAOYSA-N 0.000 claims 1
- MCOVRISDQFSJGQ-UHFFFAOYSA-N [3-(2,2-dimethylpropanoylamino)phenyl] n-(cyanomethyl)-n-phenylcarbamate Chemical compound CC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=CC=CC=2)=C1 MCOVRISDQFSJGQ-UHFFFAOYSA-N 0.000 claims 1
- OHIXSZWCCSCQTQ-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] n-(2-hydroxyethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCO)C(=O)OC(C=1)=CC=CC=1NC(=O)C1CC1 OHIXSZWCCSCQTQ-UHFFFAOYSA-N 0.000 claims 1
- CQLLDGJLAZLONP-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] n-(3-amino-3-oxopropyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCC(=O)N)C(=O)OC(C=1)=CC=CC=1NC(=O)C1CC1 CQLLDGJLAZLONP-UHFFFAOYSA-N 0.000 claims 1
- YYBRWPWPSLKFGX-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-(1-cyano-2-phenylethyl)-N-methylcarbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C)C(CC1=CC=CC=C1)C#N)=O YYBRWPWPSLKFGX-UHFFFAOYSA-N 0.000 claims 1
- JUERILWLFKYVPX-UHFFFAOYSA-N [3-(propanoylamino)phenyl] N-(2-methoxyethyl)-N-phenylcarbamate Chemical compound C(CC)(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CCOC)=O JUERILWLFKYVPX-UHFFFAOYSA-N 0.000 claims 1
- CLIHDXLFYARIOL-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2,2-dimethoxyethyl)-n-(2-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC(OC)OC)C=2C(=CC=CC=2)C)=C1 CLIHDXLFYARIOL-UHFFFAOYSA-N 0.000 claims 1
- DYOGIWRZDKNHIV-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2,2-dimethoxyethyl)-n-(3-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC(OC)OC)C=2C=C(C)C=CC=2)=C1 DYOGIWRZDKNHIV-UHFFFAOYSA-N 0.000 claims 1
- HVZZYZVMKGECLG-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2,2-dimethoxyethyl)-n-(4-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC(OC)OC)C=2C=CC(C)=CC=2)=C1 HVZZYZVMKGECLG-UHFFFAOYSA-N 0.000 claims 1
- BRTXEENUBBKSBG-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-bromoethyl)-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCBr)C=2C=CC=CC=2)=C1 BRTXEENUBBKSBG-UHFFFAOYSA-N 0.000 claims 1
- RRUKKXYUYBMUOJ-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-ethoxyethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCOCC)C(=O)OC1=CC=CC(NC(=O)CC)=C1 RRUKKXYUYBMUOJ-UHFFFAOYSA-N 0.000 claims 1
- XKWFATJZJBHDCU-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-methoxyethyl)-n-(3-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCOC)C=2C=C(C)C=CC=2)=C1 XKWFATJZJBHDCU-UHFFFAOYSA-N 0.000 claims 1
- YYILIRUYOFDRRZ-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(cyanomethyl)-n-(3-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=C(C)C=CC=2)=C1 YYILIRUYOFDRRZ-UHFFFAOYSA-N 0.000 claims 1
- ZPTPNGNBGGHVOJ-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(cyanomethyl)-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=CC=CC=2)=C1 ZPTPNGNBGGHVOJ-UHFFFAOYSA-N 0.000 claims 1
- ZAPSWDLHECRBHR-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] n-(2-methoxyethyl)-n-(3-methoxyphenyl)carbamate Chemical compound C=1C=CC(OC)=CC=1N(CCOC)C(=O)OC1=CC=CC(NC(=O)C(Cl)(Cl)Cl)=C1 ZAPSWDLHECRBHR-UHFFFAOYSA-N 0.000 claims 1
- LVYNQMRTEICUCU-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] n-(2-methoxyethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCOC)C(=O)OC1=CC=CC(NC(=O)C(Cl)(Cl)Cl)=C1 LVYNQMRTEICUCU-UHFFFAOYSA-N 0.000 claims 1
- YUQWSXJTKHKUBJ-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] n-(3-chlorophenyl)-n-(cyanomethyl)carbamate Chemical compound ClC1=CC=CC(N(CC#N)C(=O)OC=2C=C(NC(=O)C(Cl)(Cl)Cl)C=CC=2)=C1 YUQWSXJTKHKUBJ-UHFFFAOYSA-N 0.000 claims 1
- JHFJNVKBKMGBNT-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] n-(cyanomethyl)-n-phenylcarbamate Chemical compound ClC(Cl)(Cl)C(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=CC=CC=2)=C1 JHFJNVKBKMGBNT-UHFFFAOYSA-N 0.000 claims 1
- YCLYTYUHDROVLO-FARCUNLSSA-N [3-[[(e)-but-2-enoyl]amino]phenyl] n-(2-chloroethyl)-n-phenylcarbamate Chemical compound C\C=C\C(=O)NC1=CC=CC(OC(=O)N(CCCl)C=2C=CC=CC=2)=C1 YCLYTYUHDROVLO-FARCUNLSSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 12
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000969 carrier Substances 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXDRERIMPLZLU-UHFFFAOYSA-N 3-hydroxy-2-methylbutanoic acid Chemical compound CC(O)C(C)C(O)=O VEXDRERIMPLZLU-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ZAMRCGQXJHTHHA-UHFFFAOYSA-N 2-chloroethyl(phenyl)carbamic acid Chemical compound ClCCN(C(=O)O)C1=CC=CC=C1 ZAMRCGQXJHTHHA-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000905957 Channa melasoma Species 0.000 description 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FPDXDNRGGGULDX-UHFFFAOYSA-N (1-cyano-2-phenylethyl)-methylcarbamic acid Chemical compound C(#N)C(CC1=CC=CC=C1)N(C(O)=O)C FPDXDNRGGGULDX-UHFFFAOYSA-N 0.000 description 1
- HNAXBZUMENBWSX-UHFFFAOYSA-N (3-methylphenyl)carbamic acid Chemical compound CC1=CC=CC(NC(O)=O)=C1 HNAXBZUMENBWSX-UHFFFAOYSA-N 0.000 description 1
- RHNSSYGTJAAVCR-UHFFFAOYSA-N (4-methylphenyl)carbamic acid Chemical compound CC1=CC=C(NC(O)=O)C=C1 RHNSSYGTJAAVCR-UHFFFAOYSA-N 0.000 description 1
- PYJOSHDBCVEHSA-UHFFFAOYSA-N 2,2-dimethoxyethyl(phenyl)carbamic acid Chemical compound COC(OC)CN(C(O)=O)C1=CC=CC=C1 PYJOSHDBCVEHSA-UHFFFAOYSA-N 0.000 description 1
- NUBKYCCXDNYHLQ-UHFFFAOYSA-N 2,2-dimethylpentanoyl chloride Chemical compound CCCC(C)(C)C(Cl)=O NUBKYCCXDNYHLQ-UHFFFAOYSA-N 0.000 description 1
- FXKCXGBBUBCRPU-GBOPCIDUSA-N 2-[(2r,4ar,8s,8ar)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid Chemical compound C1C[C@@H](C(=C)C(O)=O)C[C@H]2[C@@](C)(O)CCC[C@@]21C FXKCXGBBUBCRPU-GBOPCIDUSA-N 0.000 description 1
- IEJBEBRAATYCNM-UHFFFAOYSA-N 2-bromoethyl(phenyl)carbamic acid Chemical compound BrCCN(C(=O)O)C1=CC=CC=C1 IEJBEBRAATYCNM-UHFFFAOYSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- NVAYCFVXLGWWCD-UHFFFAOYSA-N 2-hydroxyethyl(phenyl)carbamic acid Chemical compound OCCN(C(O)=O)C1=CC=CC=C1 NVAYCFVXLGWWCD-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- VUUHXRVVDUAGOL-UHFFFAOYSA-N 3-(3-methylanilino)propanenitrile Chemical compound CC1=CC=CC(NCCC#N)=C1 VUUHXRVVDUAGOL-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- 101150034533 ATIC gene Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 244000277177 Anchusa azurea Species 0.000 description 1
- 235000017106 Anchusa azurea Nutrition 0.000 description 1
- 241000584629 Aosa Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000011331 Brassica Nutrition 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 241000209200 Bromus Species 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000132570 Centaurea Species 0.000 description 1
- 241000271942 Cerastes Species 0.000 description 1
- 241000723343 Cichorium Species 0.000 description 1
- 244000037364 Cinnamomum aromaticum Species 0.000 description 1
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- 241001233988 Erysimum cheiri Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000221079 Euphorbia <genus> Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QNVBIDULDLPCDQ-UHFFFAOYSA-N Ilicic acid Natural products CC1(O)CCC2(C)CCC(CC2C1)C(=C)C(=O)O QNVBIDULDLPCDQ-UHFFFAOYSA-N 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 244000064622 Physalis edulis Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000219295 Portulaca Species 0.000 description 1
- 101150107341 RERE gene Proteins 0.000 description 1
- 241000593769 Richardia <angiosperm> Species 0.000 description 1
- 244000124765 Salsola kali Species 0.000 description 1
- 235000007658 Salsola kali Nutrition 0.000 description 1
- 241001523302 Scholtzia Species 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- GAUSUDNBBOZKSB-UHFFFAOYSA-N methyl(phenyl)carbamic acid Chemical compound OC(=O)N(C)C1=CC=CC=C1 GAUSUDNBBOZKSB-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 101150066242 outO gene Proteins 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229950008352 promoxolane Drugs 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RHHHGLCTQKINES-UHFFFAOYSA-M sodium;5-amino-2-methoxy-4-sulfobenzenesulfonate Chemical compound [Na+].COC1=CC(S(O)(=O)=O)=C(N)C=C1S([O-])(=O)=O RHHHGLCTQKINES-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D317/10—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
- C07D317/28—Radicals substituted by nitrogen atoms
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2844811.5 | 1978-10-12 | ||
| DE19782844811 DE2844811A1 (de) | 1978-10-12 | 1978-10-12 | Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1124251A true CA1124251A (en) | 1982-05-25 |
Family
ID=6052188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA337,402A Expired CA1124251A (en) | 1978-10-12 | 1979-10-11 | Herbicidally active carbamic acid phenyl esters and their manufacture and use |
Country Status (33)
| Country | Link |
|---|---|
| JP (1) | JPS5817744B2 (cs) |
| AR (1) | AR223188A1 (cs) |
| AT (1) | AT368360B (cs) |
| AU (1) | AU522297B2 (cs) |
| BE (1) | BE879388A (cs) |
| BR (1) | BR7906612A (cs) |
| CA (1) | CA1124251A (cs) |
| CH (1) | CH641768A5 (cs) |
| CS (1) | CS208137B2 (cs) |
| DD (1) | DD146540A5 (cs) |
| DE (1) | DE2844811A1 (cs) |
| EG (1) | EG13844A (cs) |
| ES (1) | ES484478A1 (cs) |
| FI (1) | FI792941A7 (cs) |
| FR (1) | FR2438648A1 (cs) |
| GB (1) | GB2033383B (cs) |
| GR (1) | GR74033B (cs) |
| HU (1) | HU185779B (cs) |
| IL (1) | IL58420A (cs) |
| IN (1) | IN153182B (cs) |
| IT (1) | IT1162589B (cs) |
| MA (1) | MA18607A1 (cs) |
| MX (1) | MX5735E (cs) |
| NL (1) | NL7906019A (cs) |
| PH (1) | PH15549A (cs) |
| PL (1) | PL119533B1 (cs) |
| PT (1) | PT70232A (cs) |
| RO (1) | RO79322A (cs) |
| SE (1) | SE7908273L (cs) |
| SU (1) | SU1083906A3 (cs) |
| TR (1) | TR20602A (cs) |
| YU (1) | YU204979A (cs) |
| ZA (1) | ZA795472B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844806A1 (de) | 1978-10-11 | 1980-04-24 | Schering Ag | Carbanilsaeure- eckige klammer auf 3-(alkylcarbonylamino)-phenyl eckige klammer zu -ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
| EP0051564A1 (de) * | 1980-10-31 | 1982-05-12 | Ciba-Geigy Ag | Neue Carbamate |
| WO1998047864A2 (en) * | 1997-04-21 | 1998-10-29 | Novartis Ag | N-acetalalkylcarbamates, processes for their preparation and their use as herbicides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865867A (en) * | 1967-06-19 | 1975-02-11 | Monsanto Co | Meta-bifunctional benzenes |
| CA975775A (en) * | 1969-03-12 | 1975-10-07 | Eugene G. Teach | Bromoacetanilides and their utility as biocides |
| FR2210186A5 (en) * | 1972-12-13 | 1974-07-05 | Rhone Progil | Halogenated ureidophenyl carbamates - herbicides, by reacting corresp. halophenols and isocyanates |
-
1978
- 1978-10-12 DE DE19782844811 patent/DE2844811A1/de not_active Withdrawn
-
1979
- 1979-08-06 NL NL7906019A patent/NL7906019A/nl not_active Application Discontinuation
- 1979-08-21 YU YU02049/79A patent/YU204979A/xx unknown
- 1979-09-14 IN IN644/DEL/79A patent/IN153182B/en unknown
- 1979-09-21 FI FI792941A patent/FI792941A7/fi not_active Application Discontinuation
- 1979-09-26 ES ES484478A patent/ES484478A1/es not_active Expired
- 1979-09-26 PT PT70232A patent/PT70232A/pt unknown
- 1979-09-27 MX MX798406U patent/MX5735E/es unknown
- 1979-09-28 TR TR20602A patent/TR20602A/xx unknown
- 1979-10-01 GB GB7933946A patent/GB2033383B/en not_active Expired
- 1979-10-02 MA MA18807A patent/MA18607A1/fr unknown
- 1979-10-05 SE SE7908273A patent/SE7908273L/xx not_active Application Discontinuation
- 1979-10-08 DD DD79216084A patent/DD146540A5/de unknown
- 1979-10-09 IL IL58420A patent/IL58420A/xx unknown
- 1979-10-10 EG EG593/79A patent/EG13844A/xx active
- 1979-10-10 GR GR60230A patent/GR74033B/el unknown
- 1979-10-10 CH CH911579A patent/CH641768A5/de not_active IP Right Cessation
- 1979-10-10 PL PL1979218851A patent/PL119533B1/pl unknown
- 1979-10-11 BR BR7906612A patent/BR7906612A/pt unknown
- 1979-10-11 FR FR7925313A patent/FR2438648A1/fr active Granted
- 1979-10-11 HU HU79SCHE696A patent/HU185779B/hu unknown
- 1979-10-11 SU SU792824354A patent/SU1083906A3/ru active
- 1979-10-11 CA CA337,402A patent/CA1124251A/en not_active Expired
- 1979-10-11 IT IT26401/79A patent/IT1162589B/it active
- 1979-10-11 AU AU51684/79A patent/AU522297B2/en not_active Ceased
- 1979-10-11 RO RO7998910A patent/RO79322A/ro unknown
- 1979-10-11 AT AT0664579A patent/AT368360B/de not_active IP Right Cessation
- 1979-10-12 BE BE0/197628A patent/BE879388A/fr not_active IP Right Cessation
- 1979-10-12 AR AR278479A patent/AR223188A1/es active
- 1979-10-12 ZA ZA00795472A patent/ZA795472B/xx unknown
- 1979-10-12 PH PH23165A patent/PH15549A/en unknown
- 1979-10-12 CS CS796953A patent/CS208137B2/cs unknown
- 1979-10-12 JP JP54130948A patent/JPS5817744B2/ja not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1077048A (en) | Pyrazole derivatives | |
| US4293328A (en) | N-(5-t-Butyl-3-isoxazolyl)alkanamide derivatives and herbicidal compositions containing them | |
| GB1601752A (en) | Oxime derivatives and their preparation | |
| ES481024A1 (es) | Procedimiento para la preparacion de arilsulfonamidas. | |
| HUT60237A (en) | N-(iodopropargyl oxycarbonyl)-amino acid ester derivatives, microbicidal compositions comprising such compounds as active ingredient and process for using the compounds and compositions | |
| GB1590870A (en) | N-(5-t-butyl-3-isoxazolyl) alkanamide derivatives having herbicidal activity | |
| CA1124251A (en) | Herbicidally active carbamic acid phenyl esters and their manufacture and use | |
| US3967950A (en) | Combating weeds in rice with benzothiazole derivatives | |
| US4210762A (en) | 2[5-(3-Trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl] benzoates | |
| US2902356A (en) | Certain 2-phenylimino, 3-alkyl oxazolidines, compositions and methods of use as herbicides | |
| US3535101A (en) | Herbicide and algicide means | |
| US4062977A (en) | Substituted-N-(1,1-disubstituted ethyl)-α-(substituted phenoxy)-α-alkoxyacetamides and their use as miticides | |
| KR900014338A (ko) | 제초적 1,3,5-트리아진-2-일아미노카르보닐아미노 술포닐벤조산 에스테르, 이들의 제조방법 이들을 사용하는 제초방법 | |
| US4233059A (en) | 1,2,3-Triazole carboxylic acid amides and biocidal compositions containing the same | |
| GB2058071A (en) | N-aryl-N-acyl-3-amino-oxazolidin- 2-one fungicides | |
| ES8200671A1 (es) | Procedimiento para la preparacion de derivados de amidas de acidos 1,2,3-tiadiazol-5-carboxilicos | |
| US4140774A (en) | Method of combating nematodes using S-(amidocarbonyl)-methyl-O-alkyl-mono(di)thiophosphoric acid ester amides | |
| CA1123854A (en) | Herbicidally active carbamic acid phenyl esters and their manufacture and use | |
| US3971850A (en) | N-substituted-N-(1-substituted-1-methyl-2-propynyl)-α-(substituted phenoxy) alkylamides and their use as miticides | |
| US4297295A (en) | N-(Benzenesulfonyl) thiocarbamates-herbicidal antidotes | |
| PL120535B1 (en) | Pesticide or plant growth regulator and process for manufacturing sulfonanilidesenijj i sposob poluchenija sul'fonanilidov | |
| US4111682A (en) | N-(aminoalkylene thiomethyl)-N'-(aryl) urea herbicides | |
| US4247701A (en) | Certain pesticidal substituted amino lower-alkanoates or lower-alkano-thioates containing pyridyl in the ester portion | |
| CA1183857A (en) | 1,2,3-thiadiazol-5-yl-urea derivatives having a plant growth-regulating and defoliating action and their manufacture and use | |
| GB2111996A (en) | Herbicidal derivatives of tetrahydrobenzothiazole |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |