JP2009533448A5 - - Google Patents
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- Publication number
- JP2009533448A5 JP2009533448A5 JP2009505457A JP2009505457A JP2009533448A5 JP 2009533448 A5 JP2009533448 A5 JP 2009533448A5 JP 2009505457 A JP2009505457 A JP 2009505457A JP 2009505457 A JP2009505457 A JP 2009505457A JP 2009533448 A5 JP2009533448 A5 JP 2009533448A5
- Authority
- JP
- Japan
- Prior art keywords
- inhibitor
- group
- cyclopropyl
- amino
- flurazole
- 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.)
- Abandoned
Links
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 11
- -1 isoxaflutol Chemical compound 0.000 claims description 7
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims description 4
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 4
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 4
- 102000005135 Protoporphyrinogen oxidase Human genes 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 102000005396 glutamine synthetase Human genes 0.000 claims description 4
- 108020002326 glutamine synthetase Proteins 0.000 claims description 4
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical class C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 4
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims description 2
- AHXUVTKVCMOKIX-UHFFFAOYSA-N 1-bromo-4-(chloromethylsulfonyl)benzene Chemical compound ClCS(=O)(=O)C1=CC=C(Br)C=C1 AHXUVTKVCMOKIX-UHFFFAOYSA-N 0.000 claims description 2
- OHXLAOJLJWLEIP-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyl-1,3-dioxolane Chemical compound ClC(Cl)C1(C)OCCO1 OHXLAOJLJWLEIP-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 2
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 2
- 229930192334 Auxin Natural products 0.000 claims description 2
- 239000005644 Dazomet Substances 0.000 claims description 2
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 2
- 229940106987 Elongase inhibitor Drugs 0.000 claims description 2
- 239000002169 Metam Substances 0.000 claims description 2
- BWPYBAJTDILQPY-UHFFFAOYSA-N Methoxyphenone Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1=CC=CC(C)=C1 BWPYBAJTDILQPY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005643 Pelargonic acid Substances 0.000 claims description 2
- 108010081996 Photosystem I Protein Complex Proteins 0.000 claims description 2
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 2
- 208000014347 autosomal dominant hyaline body myopathy Diseases 0.000 claims description 2
- 239000002363 auxin Substances 0.000 claims description 2
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 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
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 2
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 2
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- IKVXBIIHQGXQRQ-CYBMUJFWSA-N propan-2-yl (2r)-2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N([C@H](C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-CYBMUJFWSA-N 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWAIHLIXESXTJL-UHFFFAOYSA-N aminocyclopyrachlor Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 KWAIHLIXESXTJL-UHFFFAOYSA-N 0.000 description 2
- MDWRNPOBHVLALB-UHFFFAOYSA-N aminocyclopyrachlor-methyl Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C2CC2)=N1 MDWRNPOBHVLALB-UHFFFAOYSA-N 0.000 description 2
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 1
- BJQDYHYTWDPPIV-UHFFFAOYSA-N 1-butoxypropan-2-yl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC(C)COCCCC)=NC(C2CC2)=N1 BJQDYHYTWDPPIV-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 description 1
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 description 1
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- DYSFDPGVHAGPBC-UHFFFAOYSA-N 2-butoxyethyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCOCCCC)=NC(C2CC2)=N1 DYSFDPGVHAGPBC-UHFFFAOYSA-N 0.000 description 1
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 description 1
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 1
- QDMHMEDHEMXGLO-UHFFFAOYSA-N 2-ethylhexyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC(CC)CCCC)=NC(C2CC2)=N1 QDMHMEDHEMXGLO-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- RROBAZRVYTZHGX-UHFFFAOYSA-N 3-hydroxypropyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound OCCCOC(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 RROBAZRVYTZHGX-UHFFFAOYSA-N 0.000 description 1
- BTUSKWROSWXMPG-UHFFFAOYSA-N 6-amino-2-(4-bromophenyl)-5-chloropyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C=2C=CC(Br)=CC=2)=N1 BTUSKWROSWXMPG-UHFFFAOYSA-N 0.000 description 1
- DWIDAOMPDCVMCY-UHFFFAOYSA-N 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=C(Br)C(N)=NC(C2CC2)=N1 DWIDAOMPDCVMCY-UHFFFAOYSA-N 0.000 description 1
- IFNGRCNEIXJJOA-UHFFFAOYSA-N 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C=2C=CC(Cl)=CC=2)=N1 IFNGRCNEIXJJOA-UHFFFAOYSA-N 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 239000005558 Fluroxypyr Substances 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 239000005586 Nicosulfuron Substances 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000005590 Oxyfluorfen Substances 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 239000005617 S-Metolachlor Substances 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- GKGQGHXICXHRDC-UHFFFAOYSA-N benzyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound BrC=1C(N)=NC(C2CC2)=NC=1C(=O)OCC1=CC=CC=C1 GKGQGHXICXHRDC-UHFFFAOYSA-N 0.000 description 1
- PLSRLZJGTQNHJW-UHFFFAOYSA-N benzyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound ClC=1C(N)=NC(C2CC2)=NC=1C(=O)OCC1=CC=CC=C1 PLSRLZJGTQNHJW-UHFFFAOYSA-N 0.000 description 1
- QRIQBFGOPOEBBT-UHFFFAOYSA-N butyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCCC)=NC(C2CC2)=N1 QRIQBFGOPOEBBT-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ASZOFVYKIHWIRJ-UHFFFAOYSA-N ethyl 6-amino-2-(4-bromophenyl)-5-chloropyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C=2C=CC(Br)=CC=2)=N1 ASZOFVYKIHWIRJ-UHFFFAOYSA-N 0.000 description 1
- DFNPYOBOAGIMIV-UHFFFAOYSA-N ethyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Br)C(C(=O)OCC)=NC(C2CC2)=N1 DFNPYOBOAGIMIV-UHFFFAOYSA-N 0.000 description 1
- PXCZEJRHVNHLHI-UHFFFAOYSA-N ethyl 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C=2C=CC(Cl)=CC=2)=N1 PXCZEJRHVNHLHI-UHFFFAOYSA-N 0.000 description 1
- NMPOJZJYKCNZDZ-UHFFFAOYSA-N ethyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C2CC2)=N1 NMPOJZJYKCNZDZ-UHFFFAOYSA-N 0.000 description 1
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 1
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- RDTDHIKLTPWILZ-UHFFFAOYSA-N methyl 6-amino-2-(4-bromophenyl)-5-chloropyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C=CC(Br)=CC=2)=N1 RDTDHIKLTPWILZ-UHFFFAOYSA-N 0.000 description 1
- YDLGIPUCLCBOMQ-UHFFFAOYSA-N methyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Br)C(C(=O)OC)=NC(C2CC2)=N1 YDLGIPUCLCBOMQ-UHFFFAOYSA-N 0.000 description 1
- NRMIASFSJMZYBG-UHFFFAOYSA-N methyl 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C=CC(Cl)=CC=2)=N1 NRMIASFSJMZYBG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- KLGNDEBQUZCJDW-UHFFFAOYSA-N octan-2-yl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC(C)CCCCCC)=NC(C2CC2)=N1 KLGNDEBQUZCJDW-UHFFFAOYSA-N 0.000 description 1
- XJVFEPYNJCZLSU-UHFFFAOYSA-N octyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCCCCCCC)=NC(C2CC2)=N1 XJVFEPYNJCZLSU-UHFFFAOYSA-N 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- MOLCPAFIBVEELG-UHFFFAOYSA-N propan-2-yl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC(C)C)=NC(C2CC2)=N1 MOLCPAFIBVEELG-UHFFFAOYSA-N 0.000 description 1
- ZUTZYQPFLDQYDL-UHFFFAOYSA-N propyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCC)=NC(C2CC2)=N1 ZUTZYQPFLDQYDL-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- GQVOXSBHXPZQSS-UHFFFAOYSA-M sodium;6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound [Na+].[O-]C(=O)C1=C(Br)C(N)=NC(C2CC2)=N1 GQVOXSBHXPZQSS-UHFFFAOYSA-M 0.000 description 1
- CYILDCWNUWUWEG-UHFFFAOYSA-M sodium;6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound [Na+].[O-]C(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 CYILDCWNUWUWEG-UHFFFAOYSA-M 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79065906P | 2006-04-10 | 2006-04-10 | |
| US85213906P | 2006-10-17 | 2006-10-17 | |
| PCT/US2007/008930 WO2007120706A2 (en) | 2006-04-10 | 2007-04-10 | Herbicidal mixtures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009533448A JP2009533448A (ja) | 2009-09-17 |
| JP2009533448A5 true JP2009533448A5 (https=) | 2010-06-03 |
Family
ID=38450698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009505457A Abandoned JP2009533448A (ja) | 2006-04-10 | 2007-04-10 | 除草性混合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20100285959A1 (https=) |
| EP (1) | EP2003972A2 (https=) |
| JP (1) | JP2009533448A (https=) |
| KR (1) | KR20090024120A (https=) |
| AR (1) | AR060415A1 (https=) |
| AU (1) | AU2007238732A1 (https=) |
| BR (1) | BRPI0709505A2 (https=) |
| CA (1) | CA2646143A1 (https=) |
| EA (1) | EA200870419A1 (https=) |
| EC (1) | ECSP088802A (https=) |
| IL (1) | IL193767A0 (https=) |
| MA (1) | MA30396B1 (https=) |
| MX (1) | MX2008012995A (https=) |
| TN (1) | TNSN08519A1 (https=) |
| WO (1) | WO2007120706A2 (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| MX2015011043A (es) | 2013-02-25 | 2015-10-22 | Dow Agrosciences Llc | Métodos para el control de malezas en plantíos de piña. |
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| CH595061A5 (https=) * | 1974-05-10 | 1978-01-31 | Ciba Geigy Ag | |
| EP0136976A3 (de) * | 1983-08-23 | 1985-05-15 | Ciba-Geigy Ag | Verwendung von Phenylpyrimidinen als Pflanzenregulatoren |
| US6967188B2 (en) * | 2000-05-22 | 2005-11-22 | Bayer Cropscience Ag | Selective heteroaryloxy- acetamides-based herbicides |
| TWI355894B (en) * | 2003-12-19 | 2012-01-11 | Du Pont | Herbicidal pyrimidines |
| JP5069677B2 (ja) * | 2005-05-16 | 2012-11-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 置換ピリミジンの製造方法 |
-
2007
- 2007-04-10 KR KR1020087027364A patent/KR20090024120A/ko not_active Ceased
- 2007-04-10 WO PCT/US2007/008930 patent/WO2007120706A2/en not_active Ceased
- 2007-04-10 MX MX2008012995A patent/MX2008012995A/es not_active Application Discontinuation
- 2007-04-10 EA EA200870419A patent/EA200870419A1/ru unknown
- 2007-04-10 BR BRPI0709505-8A patent/BRPI0709505A2/pt not_active Application Discontinuation
- 2007-04-10 JP JP2009505457A patent/JP2009533448A/ja not_active Abandoned
- 2007-04-10 CA CA002646143A patent/CA2646143A1/en not_active Abandoned
- 2007-04-10 AR ARP070101511A patent/AR060415A1/es not_active Application Discontinuation
- 2007-04-10 EP EP07755262A patent/EP2003972A2/en not_active Withdrawn
- 2007-04-10 US US12/296,474 patent/US20100285959A1/en not_active Abandoned
- 2007-04-10 AU AU2007238732A patent/AU2007238732A1/en not_active Abandoned
-
2008
- 2008-08-28 IL IL193767A patent/IL193767A0/en unknown
- 2008-10-08 EC EC2008008802A patent/ECSP088802A/es unknown
- 2008-11-03 MA MA31350A patent/MA30396B1/fr unknown
- 2008-12-16 TN TNP2008000519A patent/TNSN08519A1/en unknown
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