CA2177586C - 4-benzoylisoxazoles et leur utilisation en tant qu'herbicides - Google Patents
4-benzoylisoxazoles et leur utilisation en tant qu'herbicides Download PDFInfo
- Publication number
- CA2177586C CA2177586C CA002177586A CA2177586A CA2177586C CA 2177586 C CA2177586 C CA 2177586C CA 002177586 A CA002177586 A CA 002177586A CA 2177586 A CA2177586 A CA 2177586A CA 2177586 C CA2177586 C CA 2177586C
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- benzoyl
- methoxycarbonylamino
- carbon atoms
- cyclopropylisoxazole
- 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 - Fee Related
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- FGGUUGIYSOGQED-UHFFFAOYSA-N 1,2-oxazol-4-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=NOC=1 FGGUUGIYSOGQED-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 205
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 125000005843 halogen group Chemical group 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 241000196324 Embryophyta Species 0.000 claims description 56
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 230000002363 herbicidal effect Effects 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- -1 -OR5 Chemical group 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 235000013339 cereals Nutrition 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- IQWDWHSVXZMTEI-UHFFFAOYSA-N methyl n-[2-chloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-3-methylsulfanylphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Cl)C(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 IQWDWHSVXZMTEI-UHFFFAOYSA-N 0.000 claims description 3
- QSYHHXTYUJQTAA-UHFFFAOYSA-N methyl n-[6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-fluoro-3-methylsulfinylphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(F)C(S(C)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 QSYHHXTYUJQTAA-UHFFFAOYSA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- KHYYLNLLFUVMFM-UHFFFAOYSA-N propyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-propylcarbamate Chemical compound CCCOC(=O)N(CCC)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 KHYYLNLLFUVMFM-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- IUVZNBHDZYCSMA-UHFFFAOYSA-N butyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-propylcarbamate Chemical compound CCCCOC(=O)N(CCC)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 IUVZNBHDZYCSMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- VGLRHUCDFYXYTD-UHFFFAOYSA-N ethyl 5-cyclopropyl-4-[3,4-dichloro-2-[methoxycarbonyl(methyl)amino]benzoyl]-1,2-oxazole-3-carboxylate Chemical compound C=1C=C(Cl)C(Cl)=C(N(C)C(=O)OC)C=1C(=O)C=1C(C(=O)OCC)=NOC=1C1CC1 VGLRHUCDFYXYTD-UHFFFAOYSA-N 0.000 claims description 2
- PGBZAYKNWMINIU-UHFFFAOYSA-N ethyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-(trifluoromethyl)phenyl]-n-ethylcarbamate Chemical compound CCOC(=O)N(CC)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 PGBZAYKNWMINIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- HZOBWSYRCNVGMS-UHFFFAOYSA-N methyl n-[2,3-dibromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Br)C(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 HZOBWSYRCNVGMS-UHFFFAOYSA-N 0.000 claims description 2
- RNWADNXQCXETML-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 RNWADNXQCXETML-UHFFFAOYSA-N 0.000 claims description 2
- FCFFAHZMNTTYNN-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-propylcarbamate Chemical compound CCCN(C(=O)OC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 FCFFAHZMNTTYNN-UHFFFAOYSA-N 0.000 claims description 2
- KSTBLBPHFORRBS-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-(5-propan-2-yl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C(C)C)ON=C1 KSTBLBPHFORRBS-UHFFFAOYSA-N 0.000 claims description 2
- QWKQMMPHTKAHIU-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-(trifluoromethoxy)phenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC(OC(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 QWKQMMPHTKAHIU-UHFFFAOYSA-N 0.000 claims description 2
- XEJUCNXHJOCGFZ-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-methylphenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC(C)=CC=C1C(=O)C1=C(C2CC2)ON=C1 XEJUCNXHJOCGFZ-UHFFFAOYSA-N 0.000 claims description 2
- IKMCNXSKTHXBGX-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-methylsulfonylphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=CC(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 IKMCNXSKTHXBGX-UHFFFAOYSA-N 0.000 claims description 2
- ZFWNLEQONHAHHL-UHFFFAOYSA-N methyl n-[3-bromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-ethoxyphenyl]-n-ethylcarbamate Chemical compound CCOC1=C(Br)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1N(CC)C(=O)OC ZFWNLEQONHAHHL-UHFFFAOYSA-N 0.000 claims description 2
- NNZPYSCTQZOXMT-UHFFFAOYSA-N methyl n-[3-bromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-ethoxyphenyl]-n-methylcarbamate Chemical compound CCOC1=C(Br)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1N(C)C(=O)OC NNZPYSCTQZOXMT-UHFFFAOYSA-N 0.000 claims description 2
- LIYFZMVRTAMVRC-UHFFFAOYSA-N methyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-(2-methylpropyl)carbamate Chemical compound COC(=O)N(CC(C)C)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LIYFZMVRTAMVRC-UHFFFAOYSA-N 0.000 claims description 2
- OSPGHTDZIUPNNJ-UHFFFAOYSA-N methyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OSPGHTDZIUPNNJ-UHFFFAOYSA-N 0.000 claims description 2
- NFBVYGJHELEASL-UHFFFAOYSA-N methyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 NFBVYGJHELEASL-UHFFFAOYSA-N 0.000 claims description 2
- TYTDVUNTNNJKQO-UHFFFAOYSA-N methyl n-[6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2,3-difluorophenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(F)C(F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 TYTDVUNTNNJKQO-UHFFFAOYSA-N 0.000 claims description 2
- OHGTWBHELRNWNZ-UHFFFAOYSA-N n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-methylethanethioamide Chemical compound CC(=S)N(C)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OHGTWBHELRNWNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- XDIXSMXHBPUJDC-UHFFFAOYSA-N propan-2-yl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound CC(C)OC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 XDIXSMXHBPUJDC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- GVHIREICGKQCBH-UHFFFAOYSA-N butyl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound CCCCOC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 GVHIREICGKQCBH-UHFFFAOYSA-N 0.000 claims 1
- JMMHENRSQRXEHF-UHFFFAOYSA-N ethyl 5-cyclopropyl-4-[3,4-dichloro-2-[ethyl(methoxycarbonyl)amino]benzoyl]-1,2-oxazole-3-carboxylate Chemical compound C=1C=C(Cl)C(Cl)=C(N(CC)C(=O)OC)C=1C(=O)C=1C(C(=O)OCC)=NOC=1C1CC1 JMMHENRSQRXEHF-UHFFFAOYSA-N 0.000 claims 1
- MRICVLHXMFAHDL-UHFFFAOYSA-N ethyl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound CCOC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 MRICVLHXMFAHDL-UHFFFAOYSA-N 0.000 claims 1
- RRUWKRNDXRGHBS-UHFFFAOYSA-N ethyl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-methylcarbamate Chemical compound CCOC(=O)N(C)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 RRUWKRNDXRGHBS-UHFFFAOYSA-N 0.000 claims 1
- KOQVITPRXZBZFH-UHFFFAOYSA-N ethyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound CCOC(=O)N(CC)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 KOQVITPRXZBZFH-UHFFFAOYSA-N 0.000 claims 1
- NMINCEAULIHUPF-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-(trifluoromethyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 NMINCEAULIHUPF-UHFFFAOYSA-N 0.000 claims 1
- JPLJPEDMULYERK-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-(trifluoromethyl)phenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 JPLJPEDMULYERK-UHFFFAOYSA-N 0.000 claims 1
- YUVFBDOCCNYEJB-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-fluorophenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=CC(F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 YUVFBDOCCNYEJB-UHFFFAOYSA-N 0.000 claims 1
- BUTJMTSYMYKIET-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-iodophenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC(I)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BUTJMTSYMYKIET-UHFFFAOYSA-N 0.000 claims 1
- GCZRMSSKXLGVFA-UHFFFAOYSA-N methyl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=CC=CC=C1C(=O)C1=C(C2CC2)ON=C1 GCZRMSSKXLGVFA-UHFFFAOYSA-N 0.000 claims 1
- CSCZUJXAVPOYKU-UHFFFAOYSA-N methyl n-[2-chloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-3-methylsulfonylphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Cl)C(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 CSCZUJXAVPOYKU-UHFFFAOYSA-N 0.000 claims 1
- ZJVVUNUGECXNOH-UHFFFAOYSA-N methyl n-[3-bromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-(2,2,2-trifluoroethoxy)phenyl]-n-ethylcarbamate Chemical compound C1=CC(Br)=C(OCC(F)(F)F)C(N(C(=O)OC)CC)=C1C(=O)C1=C(C2CC2)ON=C1 ZJVVUNUGECXNOH-UHFFFAOYSA-N 0.000 claims 1
- CGTYJNDTDVNKLK-UHFFFAOYSA-N methyl n-[3-bromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-methoxyphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(OC)C(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 CGTYJNDTDVNKLK-UHFFFAOYSA-N 0.000 claims 1
- QCXNTPZJRSNINT-UHFFFAOYSA-N methyl n-[3-chloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-fluorophenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(F)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 QCXNTPZJRSNINT-UHFFFAOYSA-N 0.000 claims 1
- RCIRJYUEEONTLE-UHFFFAOYSA-N methyl n-[5-bromo-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=CC(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 RCIRJYUEEONTLE-UHFFFAOYSA-N 0.000 claims 1
- FOFNAIYTXWXSKC-UHFFFAOYSA-N methyl n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-propylcarbamate Chemical compound CCCN(C(=O)OC)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 FOFNAIYTXWXSKC-UHFFFAOYSA-N 0.000 claims 1
- JWAQXWZKTYMNPG-UHFFFAOYSA-N methyl n-[6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2,3-difluorophenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=C(F)C(F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 JWAQXWZKTYMNPG-UHFFFAOYSA-N 0.000 claims 1
- HRCVNUSETMQBFS-UHFFFAOYSA-N methyl n-[6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-fluoro-3-methylsulfanylphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(F)C(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 HRCVNUSETMQBFS-UHFFFAOYSA-N 0.000 claims 1
- VFGQLWBRBLLPLA-UHFFFAOYSA-N methyl n-[6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-fluoro-3-methylsulfonylphenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(F)C(S(C)(=O)=O)=CC=C1C(=O)C1=C(C2CC2)ON=C1 VFGQLWBRBLLPLA-UHFFFAOYSA-N 0.000 claims 1
- GEUSKHWRJRWVDX-UHFFFAOYSA-N n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-methylacetamide Chemical compound CC(=O)N(C)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 GEUSKHWRJRWVDX-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ZFSDSHLSGQWAGJ-UHFFFAOYSA-N propan-2-yl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-methylcarbamate Chemical compound CC(C)OC(=O)N(C)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 ZFSDSHLSGQWAGJ-UHFFFAOYSA-N 0.000 claims 1
- JNYKNWQFNQGTMC-UHFFFAOYSA-N propyl n-[2,3-dichloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylcarbamate Chemical compound CCCOC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 JNYKNWQFNQGTMC-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 141
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 59
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
- 235000019341 magnesium sulphate Nutrition 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- 238000010992 reflux Methods 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- 239000012442 inert solvent Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 15
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- 238000000605 extraction Methods 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BHYTXOGFYHQHKO-UHFFFAOYSA-N methyl 2-[bis(methylsulfonyl)amino]-4-(trifluoromethoxy)benzoate Chemical compound COC(=O)C1=CC=C(OC(F)(F)F)C=C1N(S(C)(=O)=O)S(C)(=O)=O BHYTXOGFYHQHKO-UHFFFAOYSA-N 0.000 description 1
- RIFKICOQNTTZRC-UHFFFAOYSA-N methyl 2-[bis(methylsulfonyl)amino]-4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1N(S(C)(=O)=O)S(C)(=O)=O RIFKICOQNTTZRC-UHFFFAOYSA-N 0.000 description 1
- BUYYAANIAWBJNL-UHFFFAOYSA-N methyl 2-[bis(methylsulfonyl)amino]-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C=C1N(S(C)(=O)=O)S(C)(=O)=O BUYYAANIAWBJNL-UHFFFAOYSA-N 0.000 description 1
- RFOHZISGYZMELF-UHFFFAOYSA-N methyl 2-[bis(methylsulfonyl)amino]-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C=C1N(S(C)(=O)=O)S(C)(=O)=O RFOHZISGYZMELF-UHFFFAOYSA-N 0.000 description 1
- ULFWFXHUMHWYRU-UHFFFAOYSA-N methyl 2-[methyl(methylsulfonyl)amino]-4-(trifluoromethoxy)benzoate Chemical compound COC(=O)C1=CC=C(OC(F)(F)F)C=C1N(C)S(C)(=O)=O ULFWFXHUMHWYRU-UHFFFAOYSA-N 0.000 description 1
- OWWWPXDDKGYQQO-UHFFFAOYSA-N methyl 2-[methyl(methylsulfonyl)amino]-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)C=C1N(C)S(C)(=O)=O OWWWPXDDKGYQQO-UHFFFAOYSA-N 0.000 description 1
- JLGSSTIOFMOQNG-UHFFFAOYSA-N methyl 2-amino-3,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(Cl)=C1N JLGSSTIOFMOQNG-UHFFFAOYSA-N 0.000 description 1
- MQSMXRFDHQTFDU-UHFFFAOYSA-N methyl 2-amino-3,4-difluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C(F)=C1N MQSMXRFDHQTFDU-UHFFFAOYSA-N 0.000 description 1
- DZICUHOFOOPVFM-UHFFFAOYSA-N methyl 2-amino-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)C=C1N DZICUHOFOOPVFM-UHFFFAOYSA-N 0.000 description 1
- YLSWIJBTJFWIND-UHFFFAOYSA-N methyl 2-amino-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C=C1N YLSWIJBTJFWIND-UHFFFAOYSA-N 0.000 description 1
- BIFARHLBYAKSSN-UHFFFAOYSA-N methyl 2-bromo-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1Br BIFARHLBYAKSSN-UHFFFAOYSA-N 0.000 description 1
- WMGONWIUPOYJQQ-UHFFFAOYSA-N methyl 3,4-dichloro-2-(methanesulfonamido)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(Cl)=C1NS(C)(=O)=O WMGONWIUPOYJQQ-UHFFFAOYSA-N 0.000 description 1
- MVZYSIWVGBIYBN-UHFFFAOYSA-N methyl 3,4-dichloro-2-[methoxycarbonyl(methyl)amino]benzoate Chemical compound COC(=O)N(C)C1=C(Cl)C(Cl)=CC=C1C(=O)OC MVZYSIWVGBIYBN-UHFFFAOYSA-N 0.000 description 1
- OLTDNLKENJFAFZ-UHFFFAOYSA-N methyl 3,4-dichloro-2-[methyl(methylsulfonyl)amino]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(Cl)=C1N(C)S(C)(=O)=O OLTDNLKENJFAFZ-UHFFFAOYSA-N 0.000 description 1
- XNTVNFAZIIMTDP-UHFFFAOYSA-N methyl 3,4-difluoro-2-[methyl(methylsulfonyl)amino]benzoate Chemical compound COC(=O)C1=CC=C(F)C(F)=C1N(C)S(C)(=O)=O XNTVNFAZIIMTDP-UHFFFAOYSA-N 0.000 description 1
- CREQLNQZPGXMKQ-UHFFFAOYSA-N methyl 4-bromo-2-[ethyl(methoxycarbonyl)amino]-3-methoxybenzoate Chemical compound COC(=O)N(CC)C1=C(C(=O)OC)C=CC(Br)=C1OC CREQLNQZPGXMKQ-UHFFFAOYSA-N 0.000 description 1
- VLAMGYZNDRVRQX-UHFFFAOYSA-N methyl 4-bromo-2-[methyl(methylsulfonyl)amino]benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1N(C)S(C)(=O)=O VLAMGYZNDRVRQX-UHFFFAOYSA-N 0.000 description 1
- NETVIKRLOKDEAR-UHFFFAOYSA-N methyl 4-bromo-3-ethoxy-2-[ethyl(methoxycarbonyl)amino]benzoate Chemical compound CCOC1=C(Br)C=CC(C(=O)OC)=C1N(CC)C(=O)OC NETVIKRLOKDEAR-UHFFFAOYSA-N 0.000 description 1
- IEMXJNKSJPYUQC-UHFFFAOYSA-N methyl 4-bromo-3-ethoxy-2-[methyl(methylsulfonyl)amino]benzoate Chemical compound CCOC1=C(Br)C=CC(C(=O)OC)=C1N(C)S(C)(=O)=O IEMXJNKSJPYUQC-UHFFFAOYSA-N 0.000 description 1
- SMGVGBSTHNWJQO-UHFFFAOYSA-N methyl 4-chloro-2-(methanesulfonamido)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1NS(C)(=O)=O SMGVGBSTHNWJQO-UHFFFAOYSA-N 0.000 description 1
- RFXBCSNZZMRIMN-UHFFFAOYSA-N methyl 4-chloro-2-[2-methylpropyl(methylsulfonyl)amino]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1N(CC(C)C)S(C)(=O)=O RFXBCSNZZMRIMN-UHFFFAOYSA-N 0.000 description 1
- SDUBJJJYPKZYNW-UHFFFAOYSA-N methyl 4-chloro-2-[methyl(methylsulfonyl)amino]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1N(C)S(C)(=O)=O SDUBJJJYPKZYNW-UHFFFAOYSA-N 0.000 description 1
- BAZZERBWEWNHPP-UHFFFAOYSA-N methyl n-(1-butyl-4-carbamoylbenzimidazol-2-yl)carbamate Chemical compound C1=CC=C2N(CCCC)C(NC(=O)OC)=NC2=C1C(N)=O BAZZERBWEWNHPP-UHFFFAOYSA-N 0.000 description 1
- WSNNYWONIGVQCI-UHFFFAOYSA-N methyl n-(6-carbonochloridoyl-2,3-dichlorophenyl)-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(Cl)=O WSNNYWONIGVQCI-UHFFFAOYSA-N 0.000 description 1
- QRDHURAOKBXSPB-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-(3-cyclopropyl-3-oxopropanoyl)phenyl]-n-methylcarbamate Chemical compound COC(=O)N(C)C1=C(Cl)C(Cl)=CC=C1C(=O)CC(=O)C1CC1 QRDHURAOKBXSPB-UHFFFAOYSA-N 0.000 description 1
- UWQMCEXSVIMMDH-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-(4-methyl-3-oxopentanoyl)phenyl]-n-ethylcarbamate Chemical compound COC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)CC(=O)C(C)C UWQMCEXSVIMMDH-UHFFFAOYSA-N 0.000 description 1
- HDAGUEHYUOMAJM-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-ethylcarbamate Chemical compound C=1C=C(Cl)C(Cl)=C(N(CC)C(=O)OC)C=1C(=O)C(=COCC)C(=O)C1CC1 HDAGUEHYUOMAJM-UHFFFAOYSA-N 0.000 description 1
- FRTZRUMJJDWZQR-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-methylcarbamate Chemical compound C=1C=C(Cl)C(Cl)=C(N(C)C(=O)OC)C=1C(=O)C(=COCC)C(=O)C1CC1 FRTZRUMJJDWZQR-UHFFFAOYSA-N 0.000 description 1
- HUJUWLKRIVWRSR-UHFFFAOYSA-N methyl n-[2,3-dichloro-6-[2-(ethoxymethylidene)-4-methyl-3-oxopentanoyl]phenyl]-n-ethylcarbamate Chemical compound CCOC=C(C(=O)C(C)C)C(=O)C1=CC=C(Cl)C(Cl)=C1N(CC)C(=O)OC HUJUWLKRIVWRSR-UHFFFAOYSA-N 0.000 description 1
- NEYPYGROTSYFNQ-UHFFFAOYSA-N methyl n-[3-bromo-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]-2-(2,2,2-trifluoroethoxy)phenyl]-n-ethylcarbamate Chemical compound C=1C=C(Br)C(OCC(F)(F)F)=C(N(CC)C(=O)OC)C=1C(=O)C(=COCC)C(=O)C1CC1 NEYPYGROTSYFNQ-UHFFFAOYSA-N 0.000 description 1
- CBLZVMHWASBDNI-UHFFFAOYSA-N methyl n-[3-bromo-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]-2-ethoxyphenyl]-n-ethylcarbamate Chemical compound C=1C=C(Br)C(OCC)=C(N(CC)C(=O)OC)C=1C(=O)C(=COCC)C(=O)C1CC1 CBLZVMHWASBDNI-UHFFFAOYSA-N 0.000 description 1
- WGFZRSQGFNRDOY-UHFFFAOYSA-N methyl n-[3-bromo-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]-2-methoxyphenyl]-n-ethylcarbamate Chemical compound C=1C=C(Br)C(OC)=C(N(CC)C(=O)OC)C=1C(=O)C(=COCC)C(=O)C1CC1 WGFZRSQGFNRDOY-UHFFFAOYSA-N 0.000 description 1
- QXWZHBOHKZBHQY-UHFFFAOYSA-N n-[2,3-dibromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-ethylmethanesulfonamide Chemical compound CCN(S(C)(=O)=O)C1=C(Br)C(Br)=CC=C1C(=O)C1=C(C2CC2)ON=C1 QXWZHBOHKZBHQY-UHFFFAOYSA-N 0.000 description 1
- TXRCMWNIRHFCDS-UHFFFAOYSA-N n-[2,3-dibromo-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-ethylmethanesulfonamide Chemical compound C=1C=C(Br)C(Br)=C(N(CC)S(C)(=O)=O)C=1C(=O)C(=COCC)C(=O)C1CC1 TXRCMWNIRHFCDS-UHFFFAOYSA-N 0.000 description 1
- WLSQQLZWKQHOIQ-UHFFFAOYSA-N n-[2,3-dichloro-6-[2-(cyclopropanecarbonyl)-3-(dimethylamino)prop-2-enoyl]phenyl]-n-methylmethanesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=C(N(C)S(C)(=O)=O)C=1C(=O)C(=CN(C)C)C(=O)C1CC1 WLSQQLZWKQHOIQ-UHFFFAOYSA-N 0.000 description 1
- VBTITDXHZLSEMP-UHFFFAOYSA-N n-[2-(3-cyclopropyl-3-oxopropanoyl)-5-(trifluoromethoxy)phenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC(OC(F)(F)F)=CC=C1C(=O)CC(=O)C1CC1 VBTITDXHZLSEMP-UHFFFAOYSA-N 0.000 description 1
- GGXXUASMCGZPRH-UHFFFAOYSA-N n-[2-(3-cyclopropyl-3-oxopropanoyl)-5-(trifluoromethyl)phenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC(C(F)(F)F)=CC=C1C(=O)CC(=O)C1CC1 GGXXUASMCGZPRH-UHFFFAOYSA-N 0.000 description 1
- FMXRBXXYBZZOAS-UHFFFAOYSA-N n-[2-(3-cyclopropyl-3-oxopropanoyl)-5-iodophenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC(I)=CC=C1C(=O)CC(=O)C1CC1 FMXRBXXYBZZOAS-UHFFFAOYSA-N 0.000 description 1
- CVMSHKVULJTFRC-UHFFFAOYSA-N n-[2-(3-cyclopropyl-3-oxopropanoyl)-5-methylphenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC(C)=CC=C1C(=O)CC(=O)C1CC1 CVMSHKVULJTFRC-UHFFFAOYSA-N 0.000 description 1
- JZOCQGSZADDEPP-UHFFFAOYSA-N n-[2-(3-cyclopropyl-3-oxopropanoyl)-5-methylsulfonylphenyl]-n-ethylmethanesulfonamide Chemical compound CCN(S(C)(=O)=O)C1=CC(S(C)(=O)=O)=CC=C1C(=O)CC(=O)C1CC1 JZOCQGSZADDEPP-UHFFFAOYSA-N 0.000 description 1
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- PPNAOYMPCGDICA-UHFFFAOYSA-N n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-iodophenyl]-n-methylmethanesulfonamide Chemical compound CS(=O)(=O)N(C)C1=CC(I)=CC=C1C(=O)C1=C(C2CC2)ON=C1 PPNAOYMPCGDICA-UHFFFAOYSA-N 0.000 description 1
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- XTCLXIIPOAXFDK-UHFFFAOYSA-N n-[2-[2-(cyclopropanecarbonyl)-3-(dimethylamino)prop-2-enoyl]-5-iodophenyl]-n-methylmethanesulfonamide Chemical compound C=1C=C(I)C=C(N(C)S(C)(=O)=O)C=1C(=O)C(=CN(C)C)C(=O)C1CC1 XTCLXIIPOAXFDK-UHFFFAOYSA-N 0.000 description 1
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- HOTQWEQDXQZTCI-UHFFFAOYSA-N n-[2-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-ethylmethanesulfonamide Chemical compound C=1C=CC=C(N(CC)S(C)(=O)=O)C=1C(=O)C(=COCC)C(=O)C1CC1 HOTQWEQDXQZTCI-UHFFFAOYSA-N 0.000 description 1
- NUUQKTGDUNZXLF-UHFFFAOYSA-N n-[2-chloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-3-methylsulfanylphenyl]-n-ethylmethanesulfonamide Chemical compound CCN(S(C)(=O)=O)C1=C(Cl)C(SC)=CC=C1C(=O)C1=C(C2CC2)ON=C1 NUUQKTGDUNZXLF-UHFFFAOYSA-N 0.000 description 1
- YCTRZXQMRJWWRW-UHFFFAOYSA-N n-[3-bromo-6-(3-cyclopropyl-3-oxopropanoyl)-2-ethoxyphenyl]-n-methylmethanesulfonamide Chemical compound CCOC1=C(Br)C=CC(C(=O)CC(=O)C2CC2)=C1N(C)S(C)(=O)=O YCTRZXQMRJWWRW-UHFFFAOYSA-N 0.000 description 1
- FXRGJTHIXPJDBD-UHFFFAOYSA-N n-[3-bromo-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-ethoxyphenyl]-n-methylmethanesulfonamide Chemical compound CCOC1=C(Br)C=CC(C(=O)C2=C(ON=C2)C2CC2)=C1N(C)S(C)(=O)=O FXRGJTHIXPJDBD-UHFFFAOYSA-N 0.000 description 1
- CYHLDIGZBMAFLB-UHFFFAOYSA-N n-[3-chloro-6-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-2-fluorophenyl]-n-ethylmethanesulfonamide Chemical compound CCN(S(C)(=O)=O)C1=C(F)C(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 CYHLDIGZBMAFLB-UHFFFAOYSA-N 0.000 description 1
- DSXNDJKVMPZQAL-UHFFFAOYSA-N n-[5-bromo-2-[2-(cyclopropanecarbonyl)-3-(dimethylamino)prop-2-enoyl]phenyl]-n-methylmethanesulfonamide Chemical compound C=1C=C(Br)C=C(N(C)S(C)(=O)=O)C=1C(=O)C(=CN(C)C)C(=O)C1CC1 DSXNDJKVMPZQAL-UHFFFAOYSA-N 0.000 description 1
- YSRMITOSVLVCGM-UHFFFAOYSA-N n-[5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl]-n-propylmethanesulfonamide Chemical compound CCCN(S(C)(=O)=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 YSRMITOSVLVCGM-UHFFFAOYSA-N 0.000 description 1
- UYTPHIFZIWAHQD-UHFFFAOYSA-N n-[5-chloro-2-[2-(cyclopropanecarbonyl)-3-(dimethylamino)prop-2-enoyl]phenyl]-n-(2-methylpropyl)methanesulfonamide Chemical compound CC(C)CN(S(C)(=O)=O)C1=CC(Cl)=CC=C1C(=O)C(=CN(C)C)C(=O)C1CC1 UYTPHIFZIWAHQD-UHFFFAOYSA-N 0.000 description 1
- SRNXYLVXBLPPHN-UHFFFAOYSA-N n-[5-chloro-2-[2-(cyclopropanecarbonyl)-3-(dimethylamino)prop-2-enoyl]phenyl]-n-propylmethanesulfonamide Chemical compound CCCN(S(C)(=O)=O)C1=CC(Cl)=CC=C1C(=O)C(=CN(C)C)C(=O)C1CC1 SRNXYLVXBLPPHN-UHFFFAOYSA-N 0.000 description 1
- ZPGRTQPQGFMRFX-UHFFFAOYSA-N n-[5-chloro-2-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-methylmethanesulfonamide Chemical compound C=1C=C(Cl)C=C(N(C)S(C)(=O)=O)C=1C(=O)C(=COCC)C(=O)C1CC1 ZPGRTQPQGFMRFX-UHFFFAOYSA-N 0.000 description 1
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- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- WIOWBOXMLQJKEU-UHFFFAOYSA-N propan-2-yl 3,4-dichloro-2-[methoxycarbonyl(propan-2-yl)amino]benzoate Chemical compound COC(=O)N(C(C)C)C1=C(Cl)C(Cl)=CC=C1C(=O)OC(C)C WIOWBOXMLQJKEU-UHFFFAOYSA-N 0.000 description 1
- MRFRTDQSUCWNML-UHFFFAOYSA-N propan-2-yl n-[2,3-dichloro-6-(3-cyclopropyl-3-oxopropanoyl)phenyl]-n-ethylcarbamate Chemical compound CC(C)OC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)CC(=O)C1CC1 MRFRTDQSUCWNML-UHFFFAOYSA-N 0.000 description 1
- JQKWKMBELICBDP-UHFFFAOYSA-N propan-2-yl n-[2,3-dichloro-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-ethylcarbamate Chemical compound C=1C=C(Cl)C(Cl)=C(N(CC)C(=O)OC(C)C)C=1C(=O)C(=COCC)C(=O)C1CC1 JQKWKMBELICBDP-UHFFFAOYSA-N 0.000 description 1
- NHTVKKQELOZZME-UHFFFAOYSA-N propan-2-yl n-[2,3-dichloro-6-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl]-n-methylcarbamate Chemical compound C=1C=C(Cl)C(Cl)=C(N(C)C(=O)OC(C)C)C=1C(=O)C(=COCC)C(=O)C1CC1 NHTVKKQELOZZME-UHFFFAOYSA-N 0.000 description 1
- DAPSFSNCYOJPEI-UHFFFAOYSA-N propan-2-yl n-[2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)-5-(trifluoromethyl)phenyl]-n-ethylcarbamate Chemical compound CC(C)OC(=O)N(CC)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 DAPSFSNCYOJPEI-UHFFFAOYSA-N 0.000 description 1
- MLFTVCYPNZLIBK-UHFFFAOYSA-N propyl n-[2,3-dichloro-6-(3-cyclopropyl-3-oxopropanoyl)phenyl]-n-ethylcarbamate Chemical compound CCCOC(=O)N(CC)C1=C(Cl)C(Cl)=CC=C1C(=O)CC(=O)C1CC1 MLFTVCYPNZLIBK-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXPRGLWJJQBWRS-UHFFFAOYSA-N tert-butyl 3-cyclopropyl-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1CC1 CXPRGLWJJQBWRS-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
L'invention se rapporte à des dérivés 4-benzoylisoxazoles de la formule (I) dans laquelle R, R?1¿, R?2¿, R?3¿, X et n sont tels que définis dans la description et les revendications. L'invention se rapporte également à des compositions contenant ces dérivés, aux procédés de fabrication de ceux-ci, aux intermédiaires utilisés dans la fabrication de ces dérivés ainsi qu'à l'utilisation de ceux-ci en tant qu'herbicides.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939325618A GB9325618D0 (en) | 1993-12-15 | 1993-12-15 | New herbicides |
| GB9325618.8 | 1993-12-15 | ||
| PCT/EP1994/004051 WO1995016678A1 (fr) | 1993-12-15 | 1994-12-06 | 4-benzoylisoxazoles et leur utilisation en tant qu'herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2177586A1 CA2177586A1 (fr) | 1995-06-22 |
| CA2177586C true CA2177586C (fr) | 2005-11-01 |
Family
ID=35429651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002177586A Expired - Fee Related CA2177586C (fr) | 1993-12-15 | 1994-12-06 | 4-benzoylisoxazoles et leur utilisation en tant qu'herbicides |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2177586C (fr) |
-
1994
- 1994-12-06 CA CA002177586A patent/CA2177586C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2177586A1 (fr) | 1995-06-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |