CA2707520A1 - Herbicidal pyridazinone derivatives - Google Patents
Herbicidal pyridazinone derivatives Download PDFInfo
- Publication number
- CA2707520A1 CA2707520A1 CA2707520A CA2707520A CA2707520A1 CA 2707520 A1 CA2707520 A1 CA 2707520A1 CA 2707520 A CA2707520 A CA 2707520A CA 2707520 A CA2707520 A CA 2707520A CA 2707520 A1 CA2707520 A1 CA 2707520A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- alkyl
- pyrazol
- independently
- 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 title claims description 23
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 463
- 239000000203 mixture Substances 0.000 claims abstract description 111
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 28
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 19
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- -1 C2-alkynyl Chemical group 0.000 claims description 163
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 65
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 38
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 37
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 37
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 37
- 239000007787 solid Substances 0.000 claims description 37
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 33
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 29
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 28
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 26
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 26
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 25
- 239000003085 diluting agent Substances 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 24
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 23
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 23
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 22
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 22
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 22
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 239000004094 surface-active agent Substances 0.000 claims description 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 16
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 16
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 10
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 9
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 9
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 9
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- NNTDEBGKQSFIPU-UHFFFAOYSA-N 5-[3-(4-bromophenyl)-5-methylpyrazol-1-yl]-4-hydroxy-1h-pyridazin-6-one Chemical compound CC1=CC(C=2C=CC(Br)=CC=2)=NN1C1=C(O)C=NNC1=O NNTDEBGKQSFIPU-UHFFFAOYSA-N 0.000 claims description 5
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000006815 (C4-C10) cycloalkylaminocarbonyl group Chemical group 0.000 claims description 4
- LGPBAHMLFFMAEU-UHFFFAOYSA-N 2-[5-[3-(4-chlorophenyl)-5-methylpyrazol-1-yl]-1-methyl-6-oxopyridazin-4-yl]propan-2-yl hydrogen carbonate Chemical compound CC1=CC(C=2C=CC(Cl)=CC=2)=NN1C1=C(C(C)(C)OC(O)=O)C=NN(C)C1=O LGPBAHMLFFMAEU-UHFFFAOYSA-N 0.000 claims description 4
- GPEIGACQBZQHTR-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)-5-methyl-1,2-dihydropyrazol-3-yl]-5-hydroxy-2-methylpyridazin-3-one Chemical compound N1NC(C)=CC1(C=1C(N(C)N=CC=1O)=O)C1=CC=C(Cl)C=C1 GPEIGACQBZQHTR-UHFFFAOYSA-N 0.000 claims description 4
- LLBWVLPKWZBQFL-UHFFFAOYSA-N 5-hydroxy-2-methyl-4-[5-methyl-3-[4-(trifluoromethyl)phenyl]pyrazol-1-yl]pyridazin-3-one Chemical compound CC1=CC(C=2C=CC(=CC=2)C(F)(F)F)=NN1C1=C(O)C=NN(C)C1=O LLBWVLPKWZBQFL-UHFFFAOYSA-N 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- 101150020251 NR13 gene Proteins 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 3
- XTJOQZBBZXTTCO-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)-5-ethyl-4-methylpyrazol-1-yl]-5-hydroxy-2-methylpyridazin-3-one Chemical compound CCC1=C(C)C(C=2C=CC(Cl)=CC=2)=NN1C1=C(O)C=NN(C)C1=O XTJOQZBBZXTTCO-UHFFFAOYSA-N 0.000 claims description 2
- DWMDYLYCKPDKSM-UHFFFAOYSA-N 4-[5-ethyl-3-[4-(trifluoromethyl)phenyl]pyrazol-1-yl]-5-hydroxy-2-methylpyridazin-3-one Chemical compound CCC1=CC(C=2C=CC(=CC=2)C(F)(F)F)=NN1C1=C(O)C=NN(C)C1=O DWMDYLYCKPDKSM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 2
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 221
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
- 239000000460 chlorine Substances 0.000 description 94
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 52
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 51
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 51
- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 51
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 51
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 51
- 229940125877 compound 31 Drugs 0.000 description 51
- 229940127573 compound 38 Drugs 0.000 description 51
- 229940127113 compound 57 Drugs 0.000 description 51
- 229940126179 compound 72 Drugs 0.000 description 51
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 51
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 51
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 50
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 50
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 50
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 50
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 50
- 229940125797 compound 12 Drugs 0.000 description 50
- 229940126086 compound 21 Drugs 0.000 description 50
- 229940125807 compound 37 Drugs 0.000 description 50
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 49
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 49
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 39
- 241000196324 Embryophyta Species 0.000 description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 34
- 239000000243 solution Substances 0.000 description 34
- 229940125904 compound 1 Drugs 0.000 description 33
- 229940126214 compound 3 Drugs 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 32
- 125000001246 bromo group Chemical group Br* 0.000 description 31
- 229940125782 compound 2 Drugs 0.000 description 31
- 229940125898 compound 5 Drugs 0.000 description 31
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 239000002253 acid Substances 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 27
- 101150041968 CDC13 gene Proteins 0.000 description 26
- 239000005562 Glyphosate Substances 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 26
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 26
- 238000009472 formulation Methods 0.000 description 26
- 125000000623 heterocyclic group Chemical group 0.000 description 26
- 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 24
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 24
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 description 24
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 24
- 239000005496 Chlorsulfuron Substances 0.000 description 24
- 239000005499 Clomazone Substances 0.000 description 24
- 239000005507 Diflufenican Substances 0.000 description 24
- 239000005531 Flufenacet Substances 0.000 description 24
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 24
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 description 24
- 239000005981 Imazaquin Substances 0.000 description 24
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 24
- 239000005578 Mesotrione Substances 0.000 description 24
- 239000005583 Metribuzin Substances 0.000 description 24
- 239000005584 Metsulfuron-methyl Substances 0.000 description 24
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- 239000005616 Rimsulfuron Substances 0.000 description 24
- 239000005617 S-Metolachlor Substances 0.000 description 24
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
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- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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- KCQJLTOSSVXOCC-UHFFFAOYSA-N tributyl(prop-1-ynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#CC KCQJLTOSSVXOCC-UHFFFAOYSA-N 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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| US61/008,861 | 2007-12-21 | ||
| PCT/US2008/087577 WO2009086041A1 (en) | 2007-12-21 | 2008-12-19 | Herbicidal pyridazinone derivatives |
Publications (1)
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| CA2707520A1 true CA2707520A1 (en) | 2009-07-09 |
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| CA2707520A Abandoned CA2707520A1 (en) | 2007-12-21 | 2008-12-19 | Herbicidal pyridazinone derivatives |
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| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| GB0714981D0 (en) | 2007-08-01 | 2007-09-12 | Syngenta Ltd | Novel herbicides |
| US8097712B2 (en) | 2007-11-07 | 2012-01-17 | Beelogics Inc. | Compositions for conferring tolerance to viral disease in social insects, and the use thereof |
| DE102007061963A1 (de) | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| AU2009220244B2 (en) | 2008-02-29 | 2014-10-09 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| DE102008019907A1 (de) | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008028905A1 (de) | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| EP2204366A1 (de) * | 2008-12-19 | 2010-07-07 | Bayer CropScience AG | Herbizid und insektizid wirksame phenylsubstituierte Pyridazinone |
| EA019320B1 (ru) | 2008-12-22 | 2014-02-28 | Мерк Патент Гмбх | Новые полиморфные формы дигидрофосфата 6-(1-метил-1h-пиразол-4-ил)-2-{3-[5-(2-морфолин-4-илэтокси)пиримидин-2-ил]бензил}-2h-пиридазин-3-она и способы их получения |
| JP2010235591A (ja) * | 2009-03-13 | 2010-10-21 | Sumitomo Chemical Co Ltd | 除草用組成物 |
| US20120028988A1 (en) * | 2009-03-30 | 2012-02-02 | Sumitomo Chemical Company, Limited | Use of pyridazinone compound for control of harmful arthropod pests |
| US20100267706A1 (en) * | 2009-04-20 | 2010-10-21 | Institute For Oneworld Health | Compounds, Compositions and Methods Comprising Pyridazine Derivatives |
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| WO2011035878A1 (de) * | 2009-09-25 | 2011-03-31 | Bayer Cropscience Ag | Herbizid wirksame phenylsubstituierte pyridazinone |
| GB201117019D0 (en) * | 2011-10-04 | 2011-11-16 | Syngenta Ltd | Herbicidal compounds |
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| US8962584B2 (en) | 2009-10-14 | 2015-02-24 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions for controlling Varroa mites in bees |
| WO2011045271A1 (de) | 2009-10-15 | 2011-04-21 | Bayer Cropscience Ag | Herbizid wirksame heterocyclylsubstituierte pyridazinone |
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| JP5842594B2 (ja) * | 2010-12-27 | 2016-01-13 | 住友化学株式会社 | ピリダジノン化合物、それを含有する除草剤及び有害節足動物防除剤 |
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| US10760086B2 (en) | 2011-09-13 | 2020-09-01 | Monsanto Technology Llc | Methods and compositions for weed control |
| BR112014005958A2 (pt) | 2011-09-13 | 2020-10-13 | Monsanto Technology Llc | métodos e composições químicas agrícolas para controle de planta, método de redução de expressão de um gene accase em uma planta, cassete de expressão microbiana, método para fazer um polinucleotídeo, método de identificação de polinucleotídeos úteis na modulação de expressão do gene accase e composição herbicida |
| US10829828B2 (en) | 2011-09-13 | 2020-11-10 | Monsanto Technology Llc | Methods and compositions for weed control |
| MX350771B (es) | 2011-09-13 | 2017-09-15 | Monsanto Technology Llc | Métodos y composiciones para el control de malezas. |
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| CA2905027A1 (en) | 2013-03-13 | 2014-10-09 | Monsanto Technology Llc | Methods and compositions for weed control |
| MX2015012334A (es) | 2013-03-13 | 2016-02-05 | Monsanto Technology Llc | Metodos y composiciones para el control de malezas. |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| JP6668236B2 (ja) | 2013-07-19 | 2020-03-18 | モンサント テクノロジー エルエルシー | Ｌｅｐｔｉｎｏｔａｒｓａ防除用組成物及びその方法 |
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| AU2016270913A1 (en) | 2015-06-03 | 2018-01-04 | Monsanto Technology Llc | Methods and compositions for introducing nucleic acids into plants |
| GB201511631D0 (en) | 2015-07-02 | 2015-08-19 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| JP6782774B2 (ja) | 2015-10-28 | 2020-11-11 | エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ | ピリダジノン除草剤を製造するための中間体、およびそれらを製造するための方法 |
| BR112018008597B1 (pt) * | 2015-10-28 | 2022-03-03 | Fmc Corporation | Composto, composições herbicidas, mistura herbicida e método para o controle do crescimento de vegetação indesejada |
| UA123706C2 (uk) | 2016-03-30 | 2021-05-19 | Ісіхара Сангіо Кайся, Лтд. | Сполука піридазинону або її сіль і гербіцид, що містить зазначену сполуку |
| TWI785022B (zh) | 2017-03-28 | 2022-12-01 | 美商富曼西公司 | 新穎噠嗪酮類除草劑 |
| US11213030B2 (en) | 2017-06-30 | 2022-01-04 | Fmc Corporation | 4-(3,4-dihydronaphth-1-yl or 2H-chromen-4-yl)-5-hydroxy-2H-pyradizin-3-ones as herbicides |
| JP2021008405A (ja) * | 2017-09-27 | 2021-01-28 | 石原産業株式会社 | ピリダジノン系化合物又はその塩、及びそれらを含有する除草剤 |
| GB201800305D0 (en) | 2018-01-09 | 2018-02-21 | Syngenta Participations Ag | Herbicidal compounds |
| CA3088995A1 (en) | 2018-01-21 | 2019-07-25 | Fmc Corporation | Pyridazinone-substituted ketoximes as herbicides |
| CN108997325B (zh) * | 2018-07-06 | 2020-08-04 | 浙江工业大学 | 一种芳基联噻唑类化合物和应用 |
| UA129288C2 (uk) | 2018-09-27 | 2025-03-12 | ЕфЕмСі КОРПОРЕЙШН | Піридазинонові гербіциди і піридазинонові проміжні продукти, які використовуються для отримання гербіциду |
| GB201819747D0 (en) | 2018-12-04 | 2019-01-16 | Syngenta Participations Ag | Herbicidal compositions |
| US11700850B2 (en) * | 2018-12-05 | 2023-07-18 | Valent U.S.A., Llc | Aqueous herbicidal compositions and methods of use thereof |
| BR112021010152A2 (pt) * | 2018-12-20 | 2021-11-09 | Bayer Ag | Heterociclil piridazina como compostos fungicidas |
| CN113825398A (zh) * | 2019-04-01 | 2021-12-21 | 日产化学株式会社 | 哒嗪酮化合物及除草剂 |
| GB201910291D0 (en) | 2019-07-18 | 2019-09-04 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB201910290D0 (en) | 2019-07-18 | 2019-09-04 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB202012651D0 (en) | 2020-08-13 | 2020-09-30 | Syngenta Crop Protection Ag | Herbicidal compositions |
| AR125453A1 (es) | 2021-04-27 | 2023-07-19 | Bayer Ag | Piridazinonas sustituidas, sales o n-óxidos de las mismas y su uso como sustancias herbicidamente activas |
| US20250194601A1 (en) | 2022-03-30 | 2025-06-19 | Ishihara Sangyo Kaisha, Ltd. | Pyridazinone compound or salt thereof and pest control agent containing it |
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| NL126015C (enExample) * | 1964-02-12 | |||
| DE4009761A1 (de) * | 1989-07-28 | 1991-01-31 | Bayer Ag | 2h-pyridazinon-derivate |
| US5723411A (en) * | 1995-10-31 | 1998-03-03 | E. I. Du Pont De Nemours And Company | Herbicidal pyridazinones |
| JPH11152273A (ja) * | 1997-11-19 | 1999-06-08 | Otsuka Chem Co Ltd | 窒素含有６員環ジオン誘導体 |
| DE10152005A1 (de) | 2001-10-22 | 2003-04-30 | Bayer Cropscience Ag | Pyrazolylsubstituierte Heterocyclen |
| TWI375669B (en) * | 2006-03-17 | 2012-11-01 | Sumitomo Chemical Co | Pyridazinone compound and use thereof |
| EP2015638A4 (en) * | 2006-04-28 | 2010-09-29 | Redpoint Bio Corp | TRIARYL-SUBSTITUTED IMIDAZOLE DERIVATIVES AND THEIR USE AS TASTE INHIBITORS |
| JP4672695B2 (ja) * | 2007-03-22 | 2011-04-20 | 三菱電機株式会社 | 制御システム開発支援装置、制御システム開発支援方法およびその方法をコンピュータに実行させるプログラム |
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- 2008-12-19 MY MYPI20102528 patent/MY150588A/en unknown
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- 2008-12-19 UA UAA201007449A patent/UA99494C2/ru unknown
- 2008-12-19 KR KR1020107016242A patent/KR20100099735A/ko not_active Withdrawn
- 2008-12-19 EP EP08867997.2A patent/EP2225211B1/en not_active Not-in-force
- 2008-12-19 UY UY31553A patent/UY31553A1/es not_active Application Discontinuation
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2010
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| US20100267561A1 (en) | 2010-10-21 |
| EP2225211B1 (en) | 2013-10-02 |
| CN101945856A (zh) | 2011-01-12 |
| NZ585728A (en) | 2011-11-25 |
| CO6280580A2 (es) | 2011-05-20 |
| UY31553A1 (es) | 2009-08-03 |
| WO2009086041A1 (en) | 2009-07-09 |
| EP2225211A1 (en) | 2010-09-08 |
| BRPI0819528A2 (pt) | 2015-05-26 |
| AR070680A1 (es) | 2010-04-28 |
| MY150588A (en) | 2014-01-30 |
| CL2008003785A1 (es) | 2009-10-09 |
| KR20100099735A (ko) | 2010-09-13 |
| JP2011507893A (ja) | 2011-03-10 |
| UA99494C2 (ru) | 2012-08-27 |
| AU2008343031A1 (en) | 2009-07-09 |
| RU2010130559A (ru) | 2012-01-27 |
| IL206131A0 (en) | 2010-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20141219 |