DE2844811A1 - Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel - Google Patents
Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittelInfo
- Publication number
- DE2844811A1 DE2844811A1 DE19782844811 DE2844811A DE2844811A1 DE 2844811 A1 DE2844811 A1 DE 2844811A1 DE 19782844811 DE19782844811 DE 19782844811 DE 2844811 A DE2844811 A DE 2844811A DE 2844811 A1 DE2844811 A1 DE 2844811A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- ester
- acid
- deep
- propionylamino
- 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.)
- Withdrawn
Links
- -1 PHENYL ESTER Chemical class 0.000 title claims description 70
- 150000001875 compounds Chemical class 0.000 title claims description 21
- 239000002253 acid Substances 0.000 title claims description 20
- 239000004009 herbicide Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 11
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 3
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
- SGUHJLCZSRYQGI-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] n-(2,2-diethoxyethyl)-n-phenylcarbamate Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CC(OCC)OCC)C=2C=CC=CC=2)=C1 SGUHJLCZSRYQGI-UHFFFAOYSA-N 0.000 claims description 2
- HHOLCLCUFYWAER-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound C1CC1C(=O)NC(C=1)=CC=CC=1OC(=O)N(CCC#N)C1=CC=CC=C1 HHOLCLCUFYWAER-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- YXOXCGLBZWUULD-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] n-(2-cyanoethyl)-n-(3-methylphenyl)carbamate Chemical compound CC1=CC=CC(N(CCC#N)C(=O)OC=2C=C(NC(=O)C(Cl)(Cl)Cl)C=CC=2)=C1 YXOXCGLBZWUULD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 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
- AMRFFFYJGOXOHC-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] n-(2-chloroethyl)-n-phenylcarbamate Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CCCl)C=2C=CC=CC=2)=C1 AMRFFFYJGOXOHC-UHFFFAOYSA-N 0.000 claims 1
- KOEGBZHVQVCBMR-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC=CC=2)=C1 KOEGBZHVQVCBMR-UHFFFAOYSA-N 0.000 claims 1
- BXXFDCJJKPEOPN-UHFFFAOYSA-N [3-(2,2-dimethylpentanoylamino)phenyl] n-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-n-phenylcarbamate Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CC2OC(C)(C)OC2)C=2C=CC=CC=2)=C1 BXXFDCJJKPEOPN-UHFFFAOYSA-N 0.000 claims 1
- LVKDOCJKJSGYNP-UHFFFAOYSA-N [3-(2,2-dimethylpropanoylamino)phenyl] n-(2-cyanoethyl)-n-(3-methylphenyl)carbamate Chemical compound CC1=CC=CC(N(CCC#N)C(=O)OC=2C=C(NC(=O)C(C)(C)C)C=CC=2)=C1 LVKDOCJKJSGYNP-UHFFFAOYSA-N 0.000 claims 1
- DWKGJFCVJOLMMV-UHFFFAOYSA-N [3-(2,2-dimethylpropanoylamino)phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound CC(C)(C)C(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC=CC=2)=C1 DWKGJFCVJOLMMV-UHFFFAOYSA-N 0.000 claims 1
- PDYCMPFHLFWLRA-UHFFFAOYSA-N [3-(2,2-dimethylpropanoylamino)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(C)(C)C)=C1 PDYCMPFHLFWLRA-UHFFFAOYSA-N 0.000 claims 1
- JHBAASJATNBCSO-UHFFFAOYSA-N [3-(2,2-dimethylpropanoylamino)phenyl] n-(2-methoxyethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCOC)C(=O)OC1=CC=CC(NC(=O)C(C)(C)C)=C1 JHBAASJATNBCSO-UHFFFAOYSA-N 0.000 claims 1
- RNQBJFZJGVCVIZ-UHFFFAOYSA-N [3-(2-methylpropanoylamino)phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound CC(C)C(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC=CC=2)=C1 RNQBJFZJGVCVIZ-UHFFFAOYSA-N 0.000 claims 1
- YVQUGZIVNYXYQJ-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] n-(2-amino-2-oxoethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CC(=O)N)C(=O)OC(C=1)=CC=CC=1NC(=O)C1CC1 YVQUGZIVNYXYQJ-UHFFFAOYSA-N 0.000 claims 1
- OXUZNADROWQORY-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] n-(2-cyanoethyl)-n-(3-methylphenyl)carbamate Chemical compound CC1=CC=CC(N(CCC#N)C(=O)OC=2C=C(NC(=O)C3CC3)C=CC=2)=C1 OXUZNADROWQORY-UHFFFAOYSA-N 0.000 claims 1
- JCOKAJNALRMBIA-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] n-(2-methoxyethyl)-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(CCOC)C(=O)OC(C=1)=CC=CC=1NC(=O)C1CC1 JCOKAJNALRMBIA-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
- UOSIUTLZHVCXIV-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(1,3-dioxolan-2-ylmethyl)-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC2OCCO2)C=2C=CC=CC=2)=C1 UOSIUTLZHVCXIV-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
- JJLABELIMMEDQC-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2,2-dimethoxyethyl)-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC(OC)OC)C=2C=CC=CC=2)=C1 JJLABELIMMEDQC-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
- ZRFLWIVINWQDNX-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-chloroethyl)-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCCl)C=2C=CC=CC=2)=C1 ZRFLWIVINWQDNX-UHFFFAOYSA-N 0.000 claims 1
- ZTFDDSQWNMMLJZ-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-cyanoethyl)-n-(2-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C(=CC=CC=2)C)=C1 ZTFDDSQWNMMLJZ-UHFFFAOYSA-N 0.000 claims 1
- HIMIDRAUBRPPSG-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-cyanoethyl)-n-(3-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=C(C)C=CC=2)=C1 HIMIDRAUBRPPSG-UHFFFAOYSA-N 0.000 claims 1
- BSZMYPWCHZDHGX-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-cyanoethyl)-n-(4-methylphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC(C)=CC=2)=C1 BSZMYPWCHZDHGX-UHFFFAOYSA-N 0.000 claims 1
- QIRBEJLUPCBQPI-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC=CC=2)=C1 QIRBEJLUPCBQPI-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
- HDEUDGMYIXPNTM-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-(2-methoxyethyl)-n-(3-methoxyphenyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCOC)C=2C=C(OC)C=CC=2)=C1 HDEUDGMYIXPNTM-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
- RXYKFKGKMHDCFX-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-[(4-methyl-1,3-dioxolan-2-yl)methyl]-n-phenylcarbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CC2OC(C)CO2)C=2C=CC=CC=2)=C1 RXYKFKGKMHDCFX-UHFFFAOYSA-N 0.000 claims 1
- ZAWQEOWWWPUIRE-UHFFFAOYSA-N [3-(propanoylamino)phenyl] n-phenyl-n-(2-phenylethyl)carbamate Chemical compound CCC(=O)NC1=CC=CC(OC(=O)N(CCC=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ZAWQEOWWWPUIRE-UHFFFAOYSA-N 0.000 claims 1
- LBRBDTVZDBSLQE-UHFFFAOYSA-N [3-[(2,2,2-trichloroacetyl)amino]phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound ClC(Cl)(Cl)C(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC=CC=2)=C1 LBRBDTVZDBSLQE-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
- 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
- HQMOHDUTVPVMFV-KRXBUXKQSA-N [3-[[(e)-but-2-enoyl]amino]phenyl] n-(2-cyanoethyl)-n-phenylcarbamate Chemical compound C\C=C\C(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=CC=CC=2)=C1 HQMOHDUTVPVMFV-KRXBUXKQSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 16
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 7
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
- 239000007788 liquid Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- YXSKGOCVSTWEJU-UHFFFAOYSA-N n-(3-hydroxyphenyl)propanamide Chemical compound CCC(=O)NC1=CC=CC(O)=C1 YXSKGOCVSTWEJU-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229940018563 3-aminophenol Drugs 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- OGXOQHBIFOKBAX-UHFFFAOYSA-N [3-(cyclopropanecarbonylamino)phenyl] carbonochloridate Chemical compound ClC(=O)OC1=CC=CC(NC(=O)C2CC2)=C1 OGXOQHBIFOKBAX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 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
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- YMPKWMGLBHVDBS-UHFFFAOYSA-N n-(3-hydroxyphenyl)-2,2-dimethylpentanamide Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(O)=C1 YMPKWMGLBHVDBS-UHFFFAOYSA-N 0.000 description 1
- RGSXNBKIMXWTIA-UHFFFAOYSA-N n-(3-hydroxyphenyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CC=CC(O)=C1 RGSXNBKIMXWTIA-UHFFFAOYSA-N 0.000 description 1
- YTCACQVZWKHHJO-UHFFFAOYSA-N n-(cyanomethyl)-n-(3-methylphenyl)carbamoyl chloride Chemical compound CC1=CC=CC(N(CC#N)C(Cl)=O)=C1 YTCACQVZWKHHJO-UHFFFAOYSA-N 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
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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)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (32)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782844811 DE2844811A1 (de) | 1978-10-12 | 1978-10-12 | Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
| NL7906019A NL7906019A (nl) | 1978-10-12 | 1979-08-06 | Carbaminezuurfenylesters, werkwijze voor het bereiden daarvan alsmede herbiciden, die deze verbindingen bevatten. |
| YU02049/79A YU204979A (en) | 1978-10-12 | 1979-08-21 | Process for obtaining phenylesters of carbamic acid |
| IN644/DEL/79A IN153182B (pl) | 1978-10-12 | 1979-09-14 | |
| ES484478A ES484478A1 (es) | 1978-10-12 | 1979-09-26 | Procedimiento para la preparacion de esteres fenilicos de acidos carbamicos |
| PT70232A PT70232A (de) | 1978-10-12 | 1979-09-26 | Carbaminsaurephenylester verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
| MX798406U MX5735E (es) | 1978-10-12 | 1979-09-27 | Procedimiento para preparar fenil esteres de acido carbamico |
| TR20602A TR20602A (tr) | 1978-10-12 | 1979-09-28 | Karbamik asit fenil esterleri,bu bilesimlerin imaline mahsus usul ve bunlari ihtiva eden herbisit bir madde |
| GB7933946A GB2033383B (en) | 1978-10-12 | 1979-10-01 | Herbicidally active carbamic acid phenyl esters and their manufacture and use |
| MA18807A MA18607A1 (fr) | 1978-10-12 | 1979-10-02 | Carbanilates d'acylamino-3 phenyles et produits herbicides qui en contiennent |
| SE7908273A SE7908273L (sv) | 1978-10-12 | 1979-10-05 | Karbaminsyrafenylestrar, sett att framstella dessa samt herbicida medel, innehallande sadana estrar |
| DD79216084A DD146540A5 (de) | 1978-10-12 | 1979-10-08 | Herbizides mittel |
| IL58420A IL58420A (en) | 1978-10-12 | 1979-10-09 | Selective herbicidal compositions containing phenyl carbamic acid acylaminophenyl esters and methods for the use thereof |
| PL1979218851A PL119533B1 (en) | 1978-10-12 | 1979-10-10 | Herbicide |
| GR60230A GR74033B (pl) | 1978-10-12 | 1979-10-10 | |
| EG593/79A EG13844A (en) | 1978-10-12 | 1979-10-10 | Herbicidally active carbamic acid phenyl esters ana method of preparing carbamic acid phenyle esters herbicides and its uses d their manufacture and use |
| CH911579A CH641768A5 (de) | 1978-10-12 | 1979-10-10 | Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel. |
| RO7998910A RO79322A (ro) | 1978-10-12 | 1979-10-11 | Procedeu de obtinere a acizilor carbamici substituiti |
| BR7906612A BR7906612A (pt) | 1978-10-12 | 1979-10-11 | Esteres fenilicos de acido carbamico processo para a preparacao destes compostos bem como composicoes herbicidas contendo os mesmos |
| CA337,402A CA1124251A (en) | 1978-10-12 | 1979-10-11 | Herbicidally active carbamic acid phenyl esters and their manufacture and use |
| FR7925313A FR2438648A1 (fr) | 1978-10-12 | 1979-10-11 | Carbamates d'acylamino-3 phenyles et produits herbicides qui en contiennent |
| IT26401/79A IT1162589B (it) | 1978-10-12 | 1979-10-11 | Esteri fenilici dell'acido carbammico,procedimento per la preparazione di questi composti nonche' mezzo erbicida che li contiene |
| HU79SCHE696A HU185779B (en) | 1978-10-12 | 1979-10-11 | Herbicides containing carbamic acid phenyl esters |
| SU792824354A SU1083906A3 (ru) | 1978-10-12 | 1979-10-11 | Способ получени фениловых сложных эфиров карбаминовой кислоты |
| AU51684/79A AU522297B2 (en) | 1978-10-12 | 1979-10-11 | N-substituted carbamic acid esters and herbicides |
| AT0664579A AT368360B (de) | 1978-10-12 | 1979-10-11 | Herbizide mittel |
| ZA00795472A ZA795472B (en) | 1978-10-12 | 1979-10-12 | Herbicidally active carbamic acid phenyl esters and their manufacture and use |
| CS796953A CS208137B2 (en) | 1978-10-12 | 1979-10-12 | Herbicide means and method of making the active substances |
| PH23165A PH15549A (en) | 1978-10-12 | 1979-10-12 | Carbamic acid phenyl esters and a herbicidal agent containing them |
| JP54130948A JPS5817744B2 (ja) | 1978-10-12 | 1979-10-12 | カルバミン酸フェニルエステル及び該化合物を含有する除草剤 |
| BE0/197628A BE879388A (fr) | 1978-10-12 | 1979-10-12 | Carbamates de phenyle, leur procede de preparation et leur utilisation |
| AR278479A AR223188A1 (es) | 1978-10-12 | 1979-10-12 | Esteres fenilicos del acido carbamico,procedimento para producir estos compuestos y composiciones herbicidas que los contienen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| DE2844811A1 true DE2844811A1 (de) | 1980-09-04 |
Family
ID=6052188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782844811 Withdrawn DE2844811A1 (de) | 1978-10-12 | 1978-10-12 | Carbaminsaeurephenylester, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes herbizides mittel |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS5817744B2 (pl) |
| AR (1) | AR223188A1 (pl) |
| AT (1) | AT368360B (pl) |
| AU (1) | AU522297B2 (pl) |
| BE (1) | BE879388A (pl) |
| BR (1) | BR7906612A (pl) |
| CA (1) | CA1124251A (pl) |
| CH (1) | CH641768A5 (pl) |
| CS (1) | CS208137B2 (pl) |
| DD (1) | DD146540A5 (pl) |
| DE (1) | DE2844811A1 (pl) |
| EG (1) | EG13844A (pl) |
| ES (1) | ES484478A1 (pl) |
| FR (1) | FR2438648A1 (pl) |
| GB (1) | GB2033383B (pl) |
| GR (1) | GR74033B (pl) |
| HU (1) | HU185779B (pl) |
| IL (1) | IL58420A (pl) |
| IN (1) | IN153182B (pl) |
| IT (1) | IT1162589B (pl) |
| MA (1) | MA18607A1 (pl) |
| MX (1) | MX5735E (pl) |
| NL (1) | NL7906019A (pl) |
| PH (1) | PH15549A (pl) |
| PL (1) | PL119533B1 (pl) |
| PT (1) | PT70232A (pl) |
| RO (1) | RO79322A (pl) |
| SE (1) | SE7908273L (pl) |
| SU (1) | SU1083906A3 (pl) |
| TR (1) | TR20602A (pl) |
| YU (1) | YU204979A (pl) |
| ZA (1) | ZA795472B (pl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0051564A1 (de) * | 1980-10-31 | 1982-05-12 | Ciba-Geigy Ag | Neue Carbamate |
Families Citing this family (2)
| 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 |
| AU7645298A (en) * | 1997-04-21 | 1998-11-13 | Novartis Ag | Novel 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
- 1979-09-26 PT PT70232A patent/PT70232A/pt unknown
- 1979-09-26 ES ES484478A patent/ES484478A1/es not_active Expired
- 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 PL PL1979218851A patent/PL119533B1/pl unknown
- 1979-10-10 GR GR60230A patent/GR74033B/el unknown
- 1979-10-10 EG EG593/79A patent/EG13844A/xx active
- 1979-10-10 CH CH911579A patent/CH641768A5/de not_active IP Right Cessation
- 1979-10-11 SU SU792824354A patent/SU1083906A3/ru active
- 1979-10-11 AT AT0664579A patent/AT368360B/de not_active IP Right Cessation
- 1979-10-11 HU HU79SCHE696A patent/HU185779B/hu unknown
- 1979-10-11 FR FR7925313A patent/FR2438648A1/fr active Granted
- 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 RO RO7998910A patent/RO79322A/ro unknown
- 1979-10-11 AU AU51684/79A patent/AU522297B2/en not_active Ceased
- 1979-10-11 BR BR7906612A patent/BR7906612A/pt unknown
- 1979-10-12 AR AR278479A patent/AR223188A1/es active
- 1979-10-12 ZA ZA00795472A patent/ZA795472B/xx unknown
- 1979-10-12 JP JP54130948A patent/JPS5817744B2/ja not_active Expired
- 1979-10-12 BE BE0/197628A patent/BE879388A/fr not_active IP Right Cessation
- 1979-10-12 CS CS796953A patent/CS208137B2/cs unknown
- 1979-10-12 PH PH23165A patent/PH15549A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0051564A1 (de) * | 1980-10-31 | 1982-05-12 | Ciba-Geigy Ag | Neue Carbamate |
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Legal Events
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| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |