CA1128061A - Herbicidally active diurethanes and their manufacture and use - Google Patents
Herbicidally active diurethanes and their manufacture and useInfo
- Publication number
- CA1128061A CA1128061A CA343,600A CA343600A CA1128061A CA 1128061 A CA1128061 A CA 1128061A CA 343600 A CA343600 A CA 343600A CA 1128061 A CA1128061 A CA 1128061A
- Authority
- CA
- Canada
- Prior art keywords
- ester
- acid
- phenyl
- fluoro
- living plant
- 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 description 4
- 241000196324 Embryophyta Species 0.000 claims abstract description 100
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 150000002148 esters Chemical class 0.000 claims description 134
- 239000002253 acid Substances 0.000 claims description 113
- -1 halogeno-C1-C4-alkyl Chemical group 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 43
- UAEPXXFSZDCODC-UHFFFAOYSA-N ethyl-(4-fluorophenyl)carbamic acid Chemical compound C(C)N(C(O)=O)C1=CC=C(C=C1)F UAEPXXFSZDCODC-UHFFFAOYSA-N 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 7
- WZOMBBOIBCHWCP-UHFFFAOYSA-N (4-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=C(F)C=C1 WZOMBBOIBCHWCP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- KPRWEGORVIVZNZ-UHFFFAOYSA-N (4-fluorophenyl)-(2-phenylethyl)carbamic acid Chemical compound FC1=CC=C(N(C(O)=O)CCC2=CC=CC=C2)C=C1 KPRWEGORVIVZNZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- DJTODVVYZSSTCR-UHFFFAOYSA-N ethyl-(3-fluorophenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC(F)=C1 DJTODVVYZSSTCR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- QVUFBHNIVPPFEI-UHFFFAOYSA-N (3-fluorophenyl)-(2-phenylethyl)carbamic acid Chemical compound FC=1C=C(N(C(O)=O)CCC2=CC=CC=C2)C=CC1 QVUFBHNIVPPFEI-UHFFFAOYSA-N 0.000 claims description 3
- MGDDHBBPSNIXFW-UHFFFAOYSA-N (3-fluorophenyl)-methylcarbamic acid Chemical compound OC(=O)N(C)C1=CC=CC(F)=C1 MGDDHBBPSNIXFW-UHFFFAOYSA-N 0.000 claims description 3
- PATNMSXWIVJSHC-UHFFFAOYSA-N (3-fluorophenyl)-propylcarbamic acid Chemical compound FC=1C=C(N(C(O)=O)CCC)C=CC1 PATNMSXWIVJSHC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical group 0.000 claims description 3
- CNRYLCJODAIULK-UHFFFAOYSA-N (2-fluorophenyl)-(2-phenylethyl)carbamic acid Chemical compound FC1=C(N(C(O)=O)CCC2=CC=CC=C2)C=CC=C1 CNRYLCJODAIULK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical group CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
- BSAYWCZHCBTSCD-UHFFFAOYSA-N ethyl-(2-fluorophenyl)carbamic acid Chemical compound CCN(C(O)=O)C1=CC=CC=C1F BSAYWCZHCBTSCD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- VCJUJZHGRYCPGJ-UHFFFAOYSA-N butyl-(4-fluorophenyl)carbamic acid Chemical compound CCCCN(C(O)=O)C1=CC=C(F)C=C1 VCJUJZHGRYCPGJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- PCBXHSGXUDAMAR-UHFFFAOYSA-N (3,4-difluorophenyl)-ethylcarbamic acid Chemical compound CCN(C(O)=O)C1=CC=C(F)C(F)=C1 PCBXHSGXUDAMAR-UHFFFAOYSA-N 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- QGUHDFKMQXWBOT-UHFFFAOYSA-N [3-(1-chloropropan-2-yloxycarbonylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound ClCC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O QGUHDFKMQXWBOT-UHFFFAOYSA-N 0.000 claims 1
- CQSOKXLEBDACLH-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(COC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O)C CQSOKXLEBDACLH-UHFFFAOYSA-N 0.000 claims 1
- FGSLIZQPADNLKJ-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound CC(COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O)C FGSLIZQPADNLKJ-UHFFFAOYSA-N 0.000 claims 1
- SZFFDDWTAVTSJV-UHFFFAOYSA-N [3-(2-methylpropoxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-methylcarbamate Chemical compound CC(COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)C)=O)C SZFFDDWTAVTSJV-UHFFFAOYSA-N 0.000 claims 1
- KZQMDCFPKZJBGD-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CCC1=CC=CC=C1)=O KZQMDCFPKZJBGD-UHFFFAOYSA-N 0.000 claims 1
- BQOWZIACJGIPSZ-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O BQOWZIACJGIPSZ-UHFFFAOYSA-N 0.000 claims 1
- MFKALTIEVGGMSB-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC1=CC=CC=C1)=O MFKALTIEVGGMSB-UHFFFAOYSA-N 0.000 claims 1
- CEWAJOVUUOYLAG-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-methylcarbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)C)=O CEWAJOVUUOYLAG-UHFFFAOYSA-N 0.000 claims 1
- MYSIQNQUMFEQSS-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-butyl-N-(4-fluorophenyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCCC)=O MYSIQNQUMFEQSS-UHFFFAOYSA-N 0.000 claims 1
- AXXFBQZNAKMFCL-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-ethyl-N-(2-fluorophenyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O AXXFBQZNAKMFCL-UHFFFAOYSA-N 0.000 claims 1
- VUVOITBUZKNSJF-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O VUVOITBUZKNSJF-UHFFFAOYSA-N 0.000 claims 1
- WYUCWJNTCWUCEP-UHFFFAOYSA-N [3-(but-3-en-2-yloxycarbonylamino)phenyl] N-ethyl-N-(4-fluorophenyl)carbamate Chemical compound CC(C=C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CC)=O WYUCWJNTCWUCEP-UHFFFAOYSA-N 0.000 claims 1
- NSDINVRDORVCLE-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(=S)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O NSDINVRDORVCLE-UHFFFAOYSA-N 0.000 claims 1
- GVQSPZSXLCBNKH-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] N-(3,4-difluorophenyl)-N-ethylcarbamate Chemical compound CC(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=C(C=C1)F)F)CC)=O GVQSPZSXLCBNKH-UHFFFAOYSA-N 0.000 claims 1
- OCVOXGJDVMREMG-UHFFFAOYSA-N [3-(ethanethioylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound CC(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O OCVOXGJDVMREMG-UHFFFAOYSA-N 0.000 claims 1
- ZIHZVPIPUBVZCD-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O ZIHZVPIPUBVZCD-UHFFFAOYSA-N 0.000 claims 1
- CNEHQBOPRCQXOD-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CCC1=CC=CC=C1)=O CNEHQBOPRCQXOD-UHFFFAOYSA-N 0.000 claims 1
- GEKKXFFAYHKKQZ-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC1=CC=CC=C1)=O GEKKXFFAYHKKQZ-UHFFFAOYSA-N 0.000 claims 1
- IPZQWWZBDMZXGK-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O IPZQWWZBDMZXGK-UHFFFAOYSA-N 0.000 claims 1
- DPKXBXXFDHCLHM-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC1=CC=CC=C1)=O DPKXBXXFDHCLHM-UHFFFAOYSA-N 0.000 claims 1
- KOWFKCKDDCNTMU-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O KOWFKCKDDCNTMU-UHFFFAOYSA-N 0.000 claims 1
- FYFQQRONWDXWIC-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O FYFQQRONWDXWIC-UHFFFAOYSA-N 0.000 claims 1
- BCVQHUYAKQYMDY-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-propylcarbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC)=O BCVQHUYAKQYMDY-UHFFFAOYSA-N 0.000 claims 1
- VFTZASBGFWQIGJ-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-butyl-N-(4-fluorophenyl)carbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCCC)=O VFTZASBGFWQIGJ-UHFFFAOYSA-N 0.000 claims 1
- PGOWLWQMOCDWQH-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O PGOWLWQMOCDWQH-UHFFFAOYSA-N 0.000 claims 1
- IBWGLKAKCVEOSB-UHFFFAOYSA-N [3-(prop-2-ynoxycarbonylamino)phenyl] N-ethyl-N-(4-fluorophenyl)carbamate Chemical compound C(C#C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CC)=O IBWGLKAKCVEOSB-UHFFFAOYSA-N 0.000 claims 1
- YZFNPWXMDCGYET-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O YZFNPWXMDCGYET-UHFFFAOYSA-N 0.000 claims 1
- SWBQORAPFOWCCB-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O SWBQORAPFOWCCB-UHFFFAOYSA-N 0.000 claims 1
- XCRBSKWWIMBQLJ-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC1=CC=CC=C1)=O XCRBSKWWIMBQLJ-UHFFFAOYSA-N 0.000 claims 1
- JEAXLXQLSPKFHM-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-(4-fluorophenyl)-N-methylcarbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)C)=O JEAXLXQLSPKFHM-UHFFFAOYSA-N 0.000 claims 1
- GGICZMVJOHFEGG-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-butyl-N-(4-fluorophenyl)carbamate Chemical compound CCCCN(C(=O)OC1=CC(NC(=O)OC(C)C)=CC=C1)C1=CC=C(F)C=C1 GGICZMVJOHFEGG-UHFFFAOYSA-N 0.000 claims 1
- RVEISNXKEUSLQP-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-ethyl-N-(2-fluorophenyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O RVEISNXKEUSLQP-UHFFFAOYSA-N 0.000 claims 1
- RQVQNCLWWXBGJE-UHFFFAOYSA-N [3-(propan-2-yloxycarbonylamino)phenyl] N-ethyl-N-(4-fluorophenyl)carbamate Chemical compound CC(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CC)=O RQVQNCLWWXBGJE-UHFFFAOYSA-N 0.000 claims 1
- NMDCVVJAQIEDIT-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(2-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CCC1=CC=CC=C1)=O NMDCVVJAQIEDIT-UHFFFAOYSA-N 0.000 claims 1
- QUJRADKGZUBSMM-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(3-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CCC1=CC=CC=C1)=O QUJRADKGZUBSMM-UHFFFAOYSA-N 0.000 claims 1
- AGHXXYVYVZMDJH-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-(4-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC=C(C=C1)F)CCC1=CC=CC=C1)=O AGHXXYVYVZMDJH-UHFFFAOYSA-N 0.000 claims 1
- YOTPOIUFBJPVDR-UHFFFAOYSA-N [3-(propanethioylamino)phenyl] N-ethyl-N-(3-fluorophenyl)carbamate Chemical compound C(C)C(=S)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CC)=O YOTPOIUFBJPVDR-UHFFFAOYSA-N 0.000 claims 1
- MUONNMDXYOWLLS-UHFFFAOYSA-N ethyl 2-amino-3-[(3,4-difluorophenyl)-ethylcarbamoyl]oxybenzoate Chemical compound C(C)OC(=O)C=1C(=C(C=CC1)OC(N(C1=CC(=C(C=C1)F)F)CC)=O)N MUONNMDXYOWLLS-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- OXJAZZRRURFKDF-UHFFFAOYSA-N methyl 2-amino-3-[ethyl-(2-fluorophenyl)carbamoyl]oxybenzoate Chemical compound COC(=O)C=1C(=C(C=CC1)OC(N(C1=C(C=CC=C1)F)CC)=O)N OXJAZZRRURFKDF-UHFFFAOYSA-N 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 11
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000000969 carrier Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- VEXDRERIMPLZLU-UHFFFAOYSA-N 3-hydroxy-2-methylbutanoic acid Chemical compound CC(O)C(C)C(O)=O VEXDRERIMPLZLU-UHFFFAOYSA-N 0.000 description 8
- 235000002634 Solanum Nutrition 0.000 description 8
- 241000207763 Solanum Species 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- IDUFFHCIDXAHEZ-UHFFFAOYSA-N (4-fluorophenyl)-propylcarbamic acid Chemical compound FC1=CC=C(N(C(O)=O)CCC)C=C1 IDUFFHCIDXAHEZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- 241000905957 Channa melasoma Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 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
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-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
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris 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
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 241000543381 Cliftonia monophylla Species 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
- 235000019738 Limestone Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 241000610375 Sparisoma viride Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- VLCYJUKOBQMFTC-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(3,4-difluorophenyl)-N-ethylcarbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=C(C=C1)F)F)CC)=O VLCYJUKOBQMFTC-UHFFFAOYSA-N 0.000 description 1
- JQPDTEKUVAUJIQ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-(2-phenylethyl)carbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)CCC1=CC=CC=C1)=O JQPDTEKUVAUJIQ-UHFFFAOYSA-N 0.000 description 1
- CUQAZLABXWMPDB-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-(3-fluorophenyl)-N-methylcarbamate Chemical compound COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC(=CC=C1)F)C)=O CUQAZLABXWMPDB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 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
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SBNPVCZGSKLRSJ-UHFFFAOYSA-N n-ethyl-3-fluoroaniline Chemical compound CCNC1=CC=CC(F)=C1 SBNPVCZGSKLRSJ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 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 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 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
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2901658.8 | 1979-01-15 | ||
| DE19792901658 DE2901658A1 (de) | 1979-01-15 | 1979-01-15 | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128061A true CA1128061A (en) | 1982-07-20 |
Family
ID=6060757
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA343,600A Expired CA1128061A (en) | 1979-01-15 | 1980-01-14 | Herbicidally active diurethanes and their manufacture and use |
Country Status (35)
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567151C3 (de) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethane, Verfahren zur Herstellung dieser Verbindungen sowie diese enthaltende herbizide Mittel |
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| DE2413933A1 (de) * | 1974-03-20 | 1975-09-25 | Schering Ag | Diurethane mit selektiver herbizider wirkung |
| JPS5140073A (ja) * | 1974-06-28 | 1976-04-03 | Siemens Ag | Shirikonnodoopinguhoho |
| DE2557552C2 (de) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethane und herbizide Mittel, enthaltend diese Verbindungen als Wirkstoffe |
| DE2638897C2 (de) | 1976-08-28 | 1978-10-26 | Basf Ag, 6700 Ludwigshafen | Diurethane und diese enthaltende Herbizide |
| DE2650796A1 (de) * | 1976-11-03 | 1978-05-11 | Schering Ag | Diurethane, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
-
1979
- 1979-01-15 DE DE19792901658 patent/DE2901658A1/de not_active Withdrawn
- 1979-12-24 IN IN940/DEL/79A patent/IN153545B/en unknown
- 1979-12-28 FI FI794081A patent/FI794081A7/fi not_active Application Discontinuation
-
1980
- 1980-01-03 YU YU00011/80A patent/YU1180A/xx unknown
- 1980-01-08 NL NL8000112A patent/NL8000112A/nl not_active Application Discontinuation
- 1980-01-10 TR TR20529A patent/TR20529A/xx unknown
- 1980-01-11 DD DD80218424A patent/DD148709A5/de unknown
- 1980-01-11 SU SU802867755A patent/SU942587A3/ru active
- 1980-01-11 AT AT0013980A patent/AT365411B/de not_active IP Right Cessation
- 1980-01-11 PH PH23505A patent/PH15195A/en unknown
- 1980-01-11 MX MX808584U patent/MX5743E/es unknown
- 1980-01-12 EG EG21/80A patent/EG14116A/xx active
- 1980-01-14 MA MA18899A patent/MA18702A1/fr unknown
- 1980-01-14 SE SE8000278A patent/SE8000278L/xx not_active Application Discontinuation
- 1980-01-14 PT PT70692A patent/PT70692A/pt unknown
- 1980-01-14 RO RO8099869A patent/RO79454A/ro unknown
- 1980-01-14 BG BG046234A patent/BG31495A3/xx unknown
- 1980-01-14 IL IL59126A patent/IL59126A/xx unknown
- 1980-01-14 IT IT19194/80A patent/IT1130864B/it active
- 1980-01-14 GR GR60957A patent/GR71679B/el unknown
- 1980-01-14 PL PL1980221361A patent/PL125248B1/pl unknown
- 1980-01-14 CA CA343,600A patent/CA1128061A/en not_active Expired
- 1980-01-14 BG BG046235A patent/BG31465A3/xx unknown
- 1980-01-14 HU HU8063A patent/HU181682B/hu unknown
- 1980-01-15 ES ES487720A patent/ES487720A1/es not_active Expired
- 1980-01-15 FR FR8000793A patent/FR2446275A1/fr active Granted
- 1980-01-15 CH CH32280A patent/CH645343A5/de not_active IP Right Cessation
- 1980-01-15 DK DK16380A patent/DK16380A/da not_active Application Discontinuation
- 1980-01-15 GB GB8001303A patent/GB2040939B/en not_active Expired
- 1980-01-15 AR AR279638A patent/AR224143A1/es active
- 1980-01-15 ZA ZA00800244A patent/ZA80244B/xx unknown
- 1980-01-15 CS CS80312A patent/CS212336B2/cs unknown
- 1980-01-15 BE BE0/198971A patent/BE881152A/fr not_active IP Right Cessation
- 1980-01-15 AU AU54604/80A patent/AU532736B2/en not_active Ceased
- 1980-01-16 JP JP55002672A patent/JPS5823865B2/ja not_active Expired
- 1980-09-10 BR BR8000161A patent/BR8000161A/pt unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |