CA1078391A - 1-thiazolyl imidazolidinones - Google Patents
1-thiazolyl imidazolidinonesInfo
- Publication number
- CA1078391A CA1078391A CA278,390A CA278390A CA1078391A CA 1078391 A CA1078391 A CA 1078391A CA 278390 A CA278390 A CA 278390A CA 1078391 A CA1078391 A CA 1078391A
- Authority
- CA
- Canada
- Prior art keywords
- imidazolidin
- compound
- acid
- bromothiazol
- reaction mixture
- 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
- OQEJNPNAYASGQD-UHFFFAOYSA-N 1-(1,3-thiazol-2-yl)imidazolidin-2-one Chemical class O=C1NCCN1C1=NC=CS1 OQEJNPNAYASGQD-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 62
- 239000011541 reaction mixture Substances 0.000 description 53
- 238000006243 chemical reaction Methods 0.000 description 49
- 239000000047 product Substances 0.000 description 44
- 239000002904 solvent Substances 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000010992 reflux Methods 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000011521 glass Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- -1 haloakyl Chemical group 0.000 description 7
- 208000027418 Wounds and injury Diseases 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 208000014674 injury Diseases 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KJKWZYXWOZRRPA-UHFFFAOYSA-N 5-iodo-2-isocyanato-1,3-thiazole Chemical class IC1=CN=C(N=C=O)S1 KJKWZYXWOZRRPA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 3
- 239000012430 organic reaction media Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- VCRVRKQOGINERL-UHFFFAOYSA-N 2-(chloromethylamino)acetaldehyde Chemical compound ClCNCC=O VCRVRKQOGINERL-UHFFFAOYSA-N 0.000 description 2
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 2
- ULRLJDCNAUTJOS-UHFFFAOYSA-N 2-(prop-2-enylamino)acetaldehyde Chemical compound C=CCNCC=O ULRLJDCNAUTJOS-UHFFFAOYSA-N 0.000 description 2
- TYDOUWBZTWYIOY-UHFFFAOYSA-N 2-(prop-2-ynylamino)acetaldehyde Chemical compound O=CCNCC#C TYDOUWBZTWYIOY-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LWHYFENAFKIILC-UHFFFAOYSA-N 2-isocyanato-5-methylsulfonyl-1,3-thiazole Chemical class CS(=O)(=O)C1=CN=C(N=C=O)S1 LWHYFENAFKIILC-UHFFFAOYSA-N 0.000 description 2
- VBLTUIWAOQDGSJ-UHFFFAOYSA-N 3-(5-iodo-1,3-thiazol-2-yl)-1-(2-oxoethyl)-1-prop-2-ynylurea Chemical compound IC1=CN=C(NC(=O)N(CC=O)CC#C)S1 VBLTUIWAOQDGSJ-UHFFFAOYSA-N 0.000 description 2
- XMXLBDNVSIHRRA-UHFFFAOYSA-N 4,5-dimethyl-1,3-thiazol-2-amine Chemical compound CC=1N=C(N)SC=1C XMXLBDNVSIHRRA-UHFFFAOYSA-N 0.000 description 2
- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- MYHLXPNRTKXXQB-UHFFFAOYSA-N 5-bromo-2-isocyanato-1,3-thiazole Chemical class BrC1=CN=C(N=C=O)S1 MYHLXPNRTKXXQB-UHFFFAOYSA-N 0.000 description 2
- GAUYIBUYTYPEGM-UHFFFAOYSA-N 5-chloro-2-isocyanato-1,3-thiazole Chemical class ClC1=CN=C(N=C=O)S1 GAUYIBUYTYPEGM-UHFFFAOYSA-N 0.000 description 2
- QUCGCLQBVRNWSC-UHFFFAOYSA-N 5-fluoro-2-isocyanato-1,3-thiazole Chemical class FC1=CN=C(N=C=O)S1 QUCGCLQBVRNWSC-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 235000007320 Avena fatua Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000011292 Brassica rapa Nutrition 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- 235000005853 Cyperus esculentus Nutrition 0.000 description 2
- 240000001505 Cyperus odoratus Species 0.000 description 2
- 240000008853 Datura stramonium Species 0.000 description 2
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 2
- 240000003176 Digitaria ciliaris Species 0.000 description 2
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 2
- 235000005476 Digitaria cruciata Nutrition 0.000 description 2
- 235000006830 Digitaria didactyla Nutrition 0.000 description 2
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 235000014716 Eleusine indica Nutrition 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 240000001549 Ipomoea eriocarpa Species 0.000 description 2
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
- 235000008515 Setaria glauca Nutrition 0.000 description 2
- 235000001155 Setaria leucopila Nutrition 0.000 description 2
- 244000010062 Setaria pumila Species 0.000 description 2
- 240000002439 Sorghum halepense Species 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 244000209130 tickweed Species 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RLIKMXRCBKUQHE-UHFFFAOYSA-N 2-(2-bromoethylamino)acetaldehyde Chemical compound BrCCNCC=O RLIKMXRCBKUQHE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GXXXUZIRGXYDFP-UHFFFAOYSA-N 2-(4-methylphenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-N 0.000 description 1
- YTEUDCIEJDRJTM-UHFFFAOYSA-N 2-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCl YTEUDCIEJDRJTM-UHFFFAOYSA-N 0.000 description 1
- XLFRSZQTJOSMBQ-UHFFFAOYSA-N 2-(propylamino)acetaldehyde Chemical compound CCCNCC=O XLFRSZQTJOSMBQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- ICUICNRYLHKQGS-UHFFFAOYSA-N 3,4,5-trichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 ICUICNRYLHKQGS-UHFFFAOYSA-N 0.000 description 1
- TYGXKDKKKNDLOW-UHFFFAOYSA-N 3-(5-bromo-1,3-thiazol-2-yl)-1-(chloromethyl)-1-(2-oxoethyl)urea Chemical compound O=CCN(CCl)C(=O)NC1=NC=C(Br)S1 TYGXKDKKKNDLOW-UHFFFAOYSA-N 0.000 description 1
- BVGDAZBTIVRTGO-UONOGXRCSA-N 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2s)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine Chemical compound C1([C@@H](C)OC=2C(N)=NC=C(C=2)C2=CN=C(C=C2OC)N2[C@H](CNCC2)C)=C(Cl)C=CC(F)=C1Cl BVGDAZBTIVRTGO-UONOGXRCSA-N 0.000 description 1
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 description 1
- MSWNMVJRAXJETG-UHFFFAOYSA-N 3-ethylbenzenecarbothioic s-acid Chemical compound CCC1=CC=CC(C(O)=S)=C1 MSWNMVJRAXJETG-UHFFFAOYSA-N 0.000 description 1
- KUUBHOLGHXMYGR-UHFFFAOYSA-N 3-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=CC(C(O)=S)=C1 KUUBHOLGHXMYGR-UHFFFAOYSA-N 0.000 description 1
- QYKUGBMFPFOPNE-UHFFFAOYSA-N 4-(chloromethyl)-1,3-thiazol-2-amine Chemical compound NC1=NC(CCl)=CS1 QYKUGBMFPFOPNE-UHFFFAOYSA-N 0.000 description 1
- IDOSOFXOXWSFDD-UHFFFAOYSA-N 4-butylbenzenecarbothioic s-acid Chemical compound CCCCC1=CC=C(C(O)=S)C=C1 IDOSOFXOXWSFDD-UHFFFAOYSA-N 0.000 description 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- XFDCNXIWKCIBAE-UHFFFAOYSA-N 5-bromo-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.NC1=NC=C(Br)S1 XFDCNXIWKCIBAE-UHFFFAOYSA-N 0.000 description 1
- SWQWTDAWUSBMGA-UHFFFAOYSA-N 5-chloro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(Cl)S1 SWQWTDAWUSBMGA-UHFFFAOYSA-N 0.000 description 1
- HUUPNPWVDMNTAH-UHFFFAOYSA-N 5-fluoro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(F)S1 HUUPNPWVDMNTAH-UHFFFAOYSA-N 0.000 description 1
- VPSCGJGRBNAUIQ-UHFFFAOYSA-N 5-iodo-1,3-thiazol-2-amine Chemical compound NC1=NC=C(I)S1 VPSCGJGRBNAUIQ-UHFFFAOYSA-N 0.000 description 1
- GUABFMPMKJGSBQ-UHFFFAOYSA-N 5-methyl-1,3-thiazol-2-amine Chemical compound CC1=CN=C(N)S1 GUABFMPMKJGSBQ-UHFFFAOYSA-N 0.000 description 1
- YEUFRAFORHUMLC-UHFFFAOYSA-N 5-methylsulfonyl-1,3-thiazol-2-amine Chemical compound CS(=O)(=O)C1=CN=C(N)S1 YEUFRAFORHUMLC-UHFFFAOYSA-N 0.000 description 1
- 240000000321 Abutilon grandifolium Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001148727 Bromus tectorum Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- 241000320639 Leptochloa Species 0.000 description 1
- 235000003403 Limnocharis flava Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- MKJZRZRIEWBTMN-UHFFFAOYSA-N prop-2-ynoyl chloride Chemical compound ClC(=O)C#C MKJZRZRIEWBTMN-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 208000037974 severe injury Diseases 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69194176A | 1976-06-01 | 1976-06-01 | |
| US05/691,743 US4116969A (en) | 1976-06-01 | 1976-06-01 | 1-thiazolyl-5-hydroxyimidazolidinones |
| US05/691,949 US4118390A (en) | 1976-06-01 | 1976-06-01 | 1-Thiazolyl-5-acyloxyimidazolidinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078391A true CA1078391A (en) | 1980-05-27 |
Family
ID=27418548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,390A Expired CA1078391A (en) | 1976-06-01 | 1977-05-13 | 1-thiazolyl imidazolidinones |
Country Status (13)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI90869C (fi) * | 1986-11-14 | 1994-04-11 | Tanabe Seiyaku Co | Menetelmä lääkeaineena käyttökelpoisten imidatsolidinonijohdannaisten valmistamiseksi |
| JPS63274941A (ja) * | 1987-05-06 | 1988-11-11 | Minoru Morita | 写真用濃度測定器 |
| NZ574222A (en) * | 2006-08-15 | 2012-03-30 | Novartis Ag | 2-(2-Oxoimidazolidin-1-yl)-thiazole-5-carboxamide derivatives and pharmaceutical uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA747255B (en) * | 1973-11-30 | 1975-11-26 | Ici Ltd | Herbicidal heterocyclic compounds |
-
1977
- 1977-05-12 NZ NZ184081A patent/NZ184081A/xx unknown
- 1977-05-13 CA CA278,390A patent/CA1078391A/en not_active Expired
- 1977-05-13 IL IL52091A patent/IL52091A/xx unknown
- 1977-05-30 JP JP6315277A patent/JPS52148072A/ja active Granted
- 1977-05-31 MX MX775762U patent/MX4638E/es unknown
- 1977-06-01 NL NL7705992A patent/NL7705992A/xx not_active Application Discontinuation
- 1977-06-01 DE DE19772724614 patent/DE2724614A1/de not_active Ceased
- 1977-06-01 AT AT388477A patent/AT354442B/de not_active IP Right Cessation
- 1977-06-01 GB GB23189/77A patent/GB1579771A/en not_active Expired
- 1977-06-01 AU AU25729/77A patent/AU505106B2/en not_active Expired
- 1977-06-01 BR BR7703562A patent/BR7703562A/pt unknown
- 1977-06-01 FR FR7716735A patent/FR2353548A1/fr active Granted
- 1977-06-01 CH CH673377A patent/CH634201A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR7703562A (pt) | 1978-02-28 |
| JPS6134434B2 (enrdf_load_stackoverflow) | 1986-08-07 |
| AU2572977A (en) | 1978-12-07 |
| MX4638E (es) | 1982-07-14 |
| GB1579771A (en) | 1980-11-26 |
| AT354442B (de) | 1979-01-10 |
| FR2353548B1 (enrdf_load_stackoverflow) | 1984-03-02 |
| IL52091A0 (en) | 1977-07-31 |
| NZ184081A (en) | 1980-10-08 |
| ATA388477A (de) | 1979-06-15 |
| FR2353548A1 (fr) | 1977-12-30 |
| DE2724614A1 (de) | 1977-12-15 |
| CH634201A5 (en) | 1983-01-31 |
| IL52091A (en) | 1980-07-31 |
| AU505106B2 (en) | 1979-11-08 |
| NL7705992A (nl) | 1977-12-05 |
| JPS52148072A (en) | 1977-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3990879A (en) | Method of controlling aquatic weeds | |
| CA1078391A (en) | 1-thiazolyl imidazolidinones | |
| EP0382463B1 (en) | Maleimide compounds and fungicides containing them | |
| CA1073916A (en) | 1-benzothiazolyl imidazolidinones | |
| US3962272A (en) | 1h-tetrazole-1-acetate esters and acids and process therefor | |
| US4493802A (en) | Preparation of o,o'-dithiodibenzoic acids | |
| EP0002774A1 (de) | Verfahren zur Acylierung von 7-Aminocephem-derivaten | |
| DE3787030T2 (de) | 1-carboxy-1-vinyloxyiminoaminothiazol-cephalosporin-derivate und deren herstellung. | |
| CH617201A5 (enrdf_load_stackoverflow) | ||
| DE2804040A1 (de) | Verfahren zur herstellung von cephemverbindungen | |
| IL31915A (en) | Thiazolines, their preparation and pharmaceutical preparations containing them | |
| US4595408A (en) | N-m-phenyl succinimide and glutarimide derivatives and their use as herbicides | |
| EP0432563B1 (de) | 4-Substituierte 5-Chlor-2-hydrazinothiazole | |
| CH630640A5 (de) | Verfahren zur herstellung von neuem bis-trimethylsilylcefamandol. | |
| FI66363C (fi) | Foerfarande foer framstaellning av 5-merkapto-1,2,3-triazoler | |
| US4973736A (en) | Diethers of m- or p-hydroxyphenol | |
| KR800000506B1 (ko) | 1-티아디아졸일-5-아실이미다졸리딘온의 제조방법 | |
| KR870000523B1 (ko) | 피라졸 제초제의 제조방법 | |
| JPH07503233A (ja) | ４−メチル−５−（２−クロロエチル）−チアゾールおよびその同族体の新規な製法 | |
| EP0146102A2 (en) | Process for preparing benzothiazine compounds | |
| US3682944A (en) | Certain 3-methylene diaxyphenyl-rhodanines | |
| GB2038824A (en) | Preparation of 3-methyl-2- (carboxy-???-hydroxyethylamido)- quinoxaline-1,4-dioxides | |
| JPS5810386B2 (ja) | 新規なチアジアゾリルイミダゾリジノン類の製造方法 | |
| SU814279A3 (ru) | Способ получени производных7-/2-ОКСииМиНО-2-(2-АМиНОТиАзОл- 4-ил)АцЕТАМидО/-2-МЕТил-3-цЕфЕМ- 4-КАРбОНОВОй КиСлОТы B ВидЕ СиН- изОМЕРОВ,или иХ СОлЕй | |
| IL44428A (en) | 3-alkyl-1-(5-substituted-1,3,4-thiadiazol-2-yl)-5-hydroxy-2-imidazolidinones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |