JPS6135990B2 - - Google Patents
Info
- Publication number
- JPS6135990B2 JPS6135990B2 JP52058617A JP5861777A JPS6135990B2 JP S6135990 B2 JPS6135990 B2 JP S6135990B2 JP 52058617 A JP52058617 A JP 52058617A JP 5861777 A JP5861777 A JP 5861777A JP S6135990 B2 JPS6135990 B2 JP S6135990B2
- Authority
- JP
- Japan
- Prior art keywords
- mole
- imidazolidin
- reaction mixture
- acid
- desired product
- 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
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 61
- 239000011541 reaction mixture Substances 0.000 description 55
- 238000006243 chemical reaction Methods 0.000 description 51
- 239000000047 product Substances 0.000 description 49
- 238000010992 reflux Methods 0.000 description 48
- 239000011521 glass Substances 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000012360 testing method Methods 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 8
- 238000001914 filtration Methods 0.000 description 8
- -1 hydrochloric acid Chemical class 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000012047 saturated solution Substances 0.000 description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012430 organic reaction media Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- OLYMKHFDESDVLU-UHFFFAOYSA-N 1-ethyl-3-(4-methoxy-1,3-benzothiazol-2-yl)-1-(2-oxoethyl)urea Chemical compound C1=CC=C2SC(NC(=O)N(CC=O)CC)=NC2=C1OC OLYMKHFDESDVLU-UHFFFAOYSA-N 0.000 description 2
- ILGDOMACGBCIPG-UHFFFAOYSA-N 2-(ethylamino)acetaldehyde Chemical compound CCNCC=O ILGDOMACGBCIPG-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
- LEUUBUNWWVJLSX-UHFFFAOYSA-N 2-isocyanato-1,3-benzothiazole Chemical class C1=CC=C2SC(N=C=O)=NC2=C1 LEUUBUNWWVJLSX-UHFFFAOYSA-N 0.000 description 2
- WGQVLCVERKHKFM-UHFFFAOYSA-N 2-isocyanato-4-methoxy-1,3-benzothiazole Chemical class COC1=CC=CC2=C1N=C(N=C=O)S2 WGQVLCVERKHKFM-UHFFFAOYSA-N 0.000 description 2
- PPVFCNCAOMPPMI-UHFFFAOYSA-N 2-isocyanato-5-methyl-1,3-benzothiazole Chemical class CC1=CC=C2SC(N=C=O)=NC2=C1 PPVFCNCAOMPPMI-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-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
- XLTYLDJHJSCTDD-UHFFFAOYSA-N 5-fluoro-2-isocyanato-1,3-benzothiazole Chemical class FC1=CC=C2SC(N=C=O)=NC2=C1 XLTYLDJHJSCTDD-UHFFFAOYSA-N 0.000 description 2
- MELAGXOBBSTJPI-UHFFFAOYSA-N 5-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2SC(N)=NC2=C1 MELAGXOBBSTJPI-UHFFFAOYSA-N 0.000 description 2
- VMNXKIDUTPOHPO-UHFFFAOYSA-N 6-chloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1 VMNXKIDUTPOHPO-UHFFFAOYSA-N 0.000 description 2
- SLHVUKYTDRUSLD-UHFFFAOYSA-N 6-chloro-2-isocyanato-1,3-benzothiazole Chemical class ClC1=CC=C2N=C(N=C=O)SC2=C1 SLHVUKYTDRUSLD-UHFFFAOYSA-N 0.000 description 2
- YHKASBDRJLTLHH-UHFFFAOYSA-N 7-bromo-1,3-benzothiazol-2-amine Chemical compound C1=CC(Br)=C2SC(N)=NC2=C1 YHKASBDRJLTLHH-UHFFFAOYSA-N 0.000 description 2
- AJRHVJCSKTXKJW-UHFFFAOYSA-N 7-bromo-2-isocyanato-1,3-benzothiazole Chemical class BrC1=CC=CC2=C1SC(N=C=O)=N2 AJRHVJCSKTXKJW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 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
- 230000008020 evaporation Effects 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009526 moderate injury Effects 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- HZNPNVFHMDSXRL-UHFFFAOYSA-N 1-(2-bromoethyl)-1-(2-oxoethyl)-3-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]urea Chemical compound FC(F)(F)C1=CC=C2SC(NC(=O)N(CCBr)CC=O)=NC2=C1 HZNPNVFHMDSXRL-UHFFFAOYSA-N 0.000 description 1
- ZOBGADOYOQFPLG-UHFFFAOYSA-N 1-(chloromethyl)-3-(5-fluoro-1,3-benzothiazol-2-yl)-1-(2-oxoethyl)urea Chemical compound FC1=CC=C2SC(NC(=O)N(CCl)CC=O)=NC2=C1 ZOBGADOYOQFPLG-UHFFFAOYSA-N 0.000 description 1
- UVXSSCDHZLJEDQ-UHFFFAOYSA-N 1-methyl-3-(5-methyl-1,3-benzothiazol-2-yl)-1-(2-oxoethyl)urea Chemical compound CC1=CC=C2SC(NC(=O)N(CC=O)C)=NC2=C1 UVXSSCDHZLJEDQ-UHFFFAOYSA-N 0.000 description 1
- 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
- VCRVRKQOGINERL-UHFFFAOYSA-N 2-(chloromethylamino)acetaldehyde Chemical compound ClCNCC=O VCRVRKQOGINERL-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
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- XCADMFFREUUMPO-UHFFFAOYSA-N 2-isocyanato-5-(trifluoromethyl)-1,3-benzothiazole Chemical class FC(F)(F)C1=CC=C2SC(N=C=O)=NC2=C1 XCADMFFREUUMPO-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-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
- BVTGITKUTQNGCZ-UHFFFAOYSA-N 3-(7-bromo-1,3-benzothiazol-2-yl)-1-(2-oxoethyl)-1-prop-2-ynylurea Chemical compound BrC1=CC=CC2=C1SC(NC(=O)N(CC=O)CC#C)=N2 BVTGITKUTQNGCZ-UHFFFAOYSA-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
- XEEMVPPCXNTVNP-UHFFFAOYSA-N 3-chlorobutanoic acid Chemical compound CC(Cl)CC(O)=O XEEMVPPCXNTVNP-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
- YSIKHBWUBSFBRZ-UHFFFAOYSA-N 3-methoxypropanoic acid Chemical compound COCCC(O)=O YSIKHBWUBSFBRZ-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
- ZAJVZJPXCSIEQP-UHFFFAOYSA-N 4,5-dimethyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2SC(N)=NC2=C1C ZAJVZJPXCSIEQP-UHFFFAOYSA-N 0.000 description 1
- APEKLQQDISCYOG-UHFFFAOYSA-N 4-(chloromethyl)-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1CCl APEKLQQDISCYOG-UHFFFAOYSA-N 0.000 description 1
- OITNBJHJJGMFBN-UHFFFAOYSA-N 4-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCl)C=C1 OITNBJHJJGMFBN-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
- VZJCLNWCJGKJOI-UHFFFAOYSA-N 4-ethoxybutanoic acid Chemical compound CCOCCCC(O)=O VZJCLNWCJGKJOI-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
- YEBCRAVYUWNFQT-UHFFFAOYSA-N 4-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=CC2=C1N=C(N)S2 YEBCRAVYUWNFQT-UHFFFAOYSA-N 0.000 description 1
- YPBSFVVQDYXXFO-UHFFFAOYSA-N 5-(2-bromoethyl)-1,3-benzothiazol-2-amine Chemical compound BrCCC1=CC=C2SC(N)=NC2=C1 YPBSFVVQDYXXFO-UHFFFAOYSA-N 0.000 description 1
- ARKYDZKUBJMEDX-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3-benzothiazol-2-amine Chemical compound FC(F)(F)C1=CC=C2SC(N)=NC2=C1 ARKYDZKUBJMEDX-UHFFFAOYSA-N 0.000 description 1
- YHBIGBYIUMCLJS-UHFFFAOYSA-N 5-fluoro-1,3-benzothiazol-2-amine Chemical compound FC1=CC=C2SC(N)=NC2=C1 YHBIGBYIUMCLJS-UHFFFAOYSA-N 0.000 description 1
- WEDYEBJLWMPPOK-UHFFFAOYSA-N 6-(trifluoromethyl)-1,3-benzothiazol-2-amine Chemical compound C1=C(C(F)(F)F)C=C2SC(N)=NC2=C1 WEDYEBJLWMPPOK-UHFFFAOYSA-N 0.000 description 1
- DBZBJLJYSYHKJO-UHFFFAOYSA-N 6-chloro-4-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC(Cl)=CC2=C1N=C(N)S2 DBZBJLJYSYHKJO-UHFFFAOYSA-N 0.000 description 1
- CJLUXPZQUXVJNF-UHFFFAOYSA-N 6-fluoro-1,3-benzothiazol-2-amine Chemical compound C1=C(F)C=C2SC(N)=NC2=C1 CJLUXPZQUXVJNF-UHFFFAOYSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- IGNBKLCFKTYIRI-UHFFFAOYSA-N 7-chloroheptanoic acid Chemical compound OC(=O)CCCCCCCl IGNBKLCFKTYIRI-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 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
- 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
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 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
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 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
- 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
- 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
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000009528 severe injury Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
- 238000005406 washing 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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/688,447 US4055569A (en) | 1976-05-20 | 1976-05-20 | 1-Benzothiazolyl-5-acyloxyimidazolidinones |
| US05/689,427 US4054574A (en) | 1976-05-24 | 1976-05-24 | 1-Benzothiazolyl-5-amino-imidazolidinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS535163A JPS535163A (en) | 1978-01-18 |
| JPS6135990B2 true JPS6135990B2 (enrdf_load_stackoverflow) | 1986-08-15 |
Family
ID=27104227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5861777A Granted JPS535163A (en) | 1976-05-20 | 1977-05-20 | 11benzothiazolyllimidazolidianes |
Country Status (12)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL59334A (en) * | 1979-03-02 | 1984-01-31 | Velsicol Chemical Corp | Tetrahydrobenzothiazolylimidazolidinones and herbicidal compositions containing them |
| JPS57175189A (en) * | 1981-04-21 | 1982-10-28 | Kyowa Hakko Kogyo Co Ltd | Benzothiazole derivative and its preparation |
| JPS58110582A (ja) * | 1981-12-24 | 1983-07-01 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1817119A1 (de) * | 1968-12-27 | 1970-07-09 | Bayer Ag | Imidazolidinon-Derivate und ihre Verwendung als Herbizide |
-
1977
- 1977-05-12 NZ NZ184082A patent/NZ184082A/xx unknown
- 1977-05-13 CA CA278,345A patent/CA1073916A/en not_active Expired
- 1977-05-13 AT AT344877A patent/AT354441B/de not_active IP Right Cessation
- 1977-05-13 IL IL52092A patent/IL52092A/xx unknown
- 1977-05-18 NL NL7705495A patent/NL7705495A/xx not_active Application Discontinuation
- 1977-05-19 AR AR267704A patent/AR225268A1/es active
- 1977-05-20 JP JP5861777A patent/JPS535163A/ja active Granted
- 1977-05-20 DE DE19772722949 patent/DE2722949A1/de not_active Ceased
- 1977-05-20 FR FR7715546A patent/FR2351977A1/fr active Granted
- 1977-05-20 CH CH627177A patent/CH633411A5/de not_active IP Right Cessation
- 1977-05-20 BR BR3284/77A patent/BR7703284A/pt unknown
- 1977-05-30 MX MX775757U patent/MX4834E/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2351977A1 (fr) | 1977-12-16 |
| IL52092A0 (en) | 1977-07-31 |
| IL52092A (en) | 1980-10-26 |
| AT354441B (de) | 1979-01-10 |
| NZ184082A (en) | 1980-05-27 |
| BR7703284A (pt) | 1978-01-31 |
| CA1073916A (en) | 1980-03-18 |
| ATA344877A (de) | 1979-06-15 |
| JPS535163A (en) | 1978-01-18 |
| CH633411A5 (en) | 1982-12-15 |
| MX4834E (es) | 1982-10-26 |
| DE2722949A1 (de) | 1977-12-01 |
| AR225268A1 (es) | 1982-03-15 |
| NL7705495A (nl) | 1977-11-22 |
| FR2351977B1 (enrdf_load_stackoverflow) | 1982-05-14 |
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