MX2013002400A - Pirazoles fungicidas. - Google Patents
Pirazoles fungicidas.Info
- Publication number
- MX2013002400A MX2013002400A MX2013002400A MX2013002400A MX2013002400A MX 2013002400 A MX2013002400 A MX 2013002400A MX 2013002400 A MX2013002400 A MX 2013002400A MX 2013002400 A MX2013002400 A MX 2013002400A MX 2013002400 A MX2013002400 A MX 2013002400A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- methyl
- chloro
- alkyl
- independently
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 90
- 150000003217 pyrazoles Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 699
- 239000000203 mixture Substances 0.000 claims abstract description 165
- 238000000034 method Methods 0.000 claims abstract description 59
- 201000010099 disease Diseases 0.000 claims abstract description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 244000053095 fungal pathogen Species 0.000 claims abstract description 9
- -1 cyanomethyl Chemical group 0.000 claims description 269
- 239000000417 fungicide Substances 0.000 claims description 253
- 125000001424 substituent group Chemical group 0.000 claims description 154
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 125000001188 haloalkyl group Chemical group 0.000 claims description 61
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000004970 halomethyl group Chemical group 0.000 claims description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 45
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 43
- 239000007787 solid Substances 0.000 claims description 42
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- 125000004076 pyridyl group Chemical group 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 31
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 28
- 239000007788 liquid Substances 0.000 claims description 28
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 27
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 26
- 239000004094 surface-active agent Substances 0.000 claims description 24
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 20
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 150000001204 N-oxides Chemical class 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 14
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 13
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 10
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 7
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 6
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
- HZMFFXSDUMADLO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenoxy)-5-(2-chloro-4-methoxyphenyl)-1,3-dimethylpyrazole Chemical compound ClC1=CC(OC)=CC=C1C(N(N=C1C)C)=C1OC1=CC=C(F)C=C1Cl HZMFFXSDUMADLO-UHFFFAOYSA-N 0.000 claims description 2
- KAICHMJALBRCMR-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)-4-(2,4-difluorophenoxy)-1,3-dimethylpyrazole Chemical compound ClC1=CC(OC)=CC=C1C(N(N=C1C)C)=C1OC1=CC=C(F)C=C1F KAICHMJALBRCMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- FSSNPLPILKGTLI-UHFFFAOYSA-N n-(2-bromo-4-fluorophenyl)-5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=CC=C(F)C=C1Br FSSNPLPILKGTLI-UHFFFAOYSA-N 0.000 claims description 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- AWACCWQDUDMTJE-UHFFFAOYSA-N 1-[2-[4-(2,4-dichlorobenzoyl)-2,5-dimethylpyrazol-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1C(N(N=C1C)C)=C1C(=O)C1=CC=C(Cl)C=C1Cl AWACCWQDUDMTJE-UHFFFAOYSA-N 0.000 claims 1
- VPTVABWVTXURCW-UHFFFAOYSA-N 3-chloro-4-[5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]oxybenzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1OC1=CC=C(C#N)C=C1Cl VPTVABWVTXURCW-UHFFFAOYSA-N 0.000 claims 1
- SJHGDMKKYPXPKX-UHFFFAOYSA-N [3-chloro-5-(2,6-difluorophenyl)-1-methylpyrazol-4-yl]-(2-chloro-4-methoxyphenyl)methanol Chemical compound ClC1=CC(OC)=CC=C1C(O)C1=C(C=2C(=CC=CC=2F)F)N(C)N=C1Cl SJHGDMKKYPXPKX-UHFFFAOYSA-N 0.000 claims 1
- JLUJLAXFYSMHCJ-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanone Chemical compound CC1=NN(C)C(C=2C(=CC(Cl)=CC=2)Cl)=C1C(=O)C1=CC=C(F)C=C1F JLUJLAXFYSMHCJ-UHFFFAOYSA-N 0.000 claims 1
- INJNUIXFZLBSJM-UHFFFAOYSA-N [5-(2-chloro-6-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,6-dichlorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=C(Cl)C=CC=C1Cl INJNUIXFZLBSJM-UHFFFAOYSA-N 0.000 claims 1
- ZRQQNZXCQKQFOX-UHFFFAOYSA-N n,5-bis(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=CC=C(F)C=C1Cl ZRQQNZXCQKQFOX-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 135
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 93
- 230000009471 action Effects 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000011541 reaction mixture Substances 0.000 description 53
- 238000002360 preparation method Methods 0.000 description 52
- 241000196324 Embryophyta Species 0.000 description 49
- 230000002829 reductive effect Effects 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 42
- 239000000460 chlorine Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 125000005843 halogen group Chemical group 0.000 description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 239000000463 material Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 241000233866 Fungi Species 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000003480 eluent Substances 0.000 description 28
- 230000012010 growth Effects 0.000 description 28
- 238000009472 formulation Methods 0.000 description 27
- 229920006395 saturated elastomer Polymers 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 26
- 229940125773 compound 10 Drugs 0.000 description 26
- 229940126543 compound 14 Drugs 0.000 description 26
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 26
- 239000000725 suspension Substances 0.000 description 25
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 24
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 24
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 24
- 229940126214 compound 3 Drugs 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 24
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 23
- 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 23
- 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 23
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 23
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 23
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 23
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 23
- 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 23
- 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 23
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 23
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 23
- 229940126657 Compound 17 Drugs 0.000 description 23
- 229940126639 Compound 33 Drugs 0.000 description 23
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
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- 235000010296 thiabendazole Nutrition 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
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- 108700012359 toxins Proteins 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- XQJQCBDIXRIYRP-STQMWFEESA-N trans-(1S,2R)-sedaxane Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1[C@H]1[C@H](C2CC2)C1 XQJQCBDIXRIYRP-STQMWFEESA-N 0.000 description 1
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- 229940062627 tribasic potassium phosphate Drugs 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical class CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 108010013280 ubiquinol oxidase Proteins 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37915910P | 2010-09-01 | 2010-09-01 | |
| PCT/US2011/049908 WO2012030922A1 (en) | 2010-09-01 | 2011-08-31 | Fungicidal pyrazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2013002400A true MX2013002400A (es) | 2013-06-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| MX2013002400A MX2013002400A (es) | 2010-09-01 | 2011-08-31 | Pirazoles fungicidas. |
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| EP (1) | EP2611297B1 (enExample) |
| JP (1) | JP6066910B2 (enExample) |
| KR (1) | KR20130139892A (enExample) |
| CN (2) | CN105130900B (enExample) |
| AR (1) | AR082869A1 (enExample) |
| AU (1) | AU2011295998A1 (enExample) |
| BR (2) | BR122017015898B1 (enExample) |
| ES (1) | ES2546671T3 (enExample) |
| MX (1) | MX2013002400A (enExample) |
| PL (1) | PL2611297T3 (enExample) |
| TW (1) | TW201245155A (enExample) |
| UY (1) | UY33582A (enExample) |
| WO (1) | WO2012030922A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| US20140235689A1 (en) * | 2013-02-20 | 2014-08-21 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| ES2661012T3 (es) | 2013-03-28 | 2018-03-27 | Takeda Pharmaceutical Company Limited | Compuesto heterocíclico |
| TWI652012B (zh) * | 2013-05-20 | 2019-03-01 | 杜邦股份有限公司 | 殺真菌吡唑的固態形式 |
| WO2015026646A1 (en) | 2013-08-20 | 2015-02-26 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| WO2015083436A1 (ja) | 2013-12-05 | 2015-06-11 | 株式会社クレハ | 農園芸用薬剤、植物病害防除方法および植物病害防除用製品 |
| EP3078265B1 (en) * | 2013-12-05 | 2017-06-07 | Kureha Corporation | Agricultural and horticultural chemical, plant disease control method and plant disease control product |
| WO2015089800A1 (en) | 2013-12-19 | 2015-06-25 | Eli Lilly And Company | Fluorophenyl pyrazol compounds |
| WO2015171392A1 (en) | 2014-05-06 | 2015-11-12 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| BR112017001350A2 (pt) | 2014-07-24 | 2017-11-14 | Bayer Cropscience Ag | derivados de pirazol fungicidas |
| US20180042234A1 (en) | 2015-03-19 | 2018-02-15 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| WO2016201662A1 (en) * | 2015-06-18 | 2016-12-22 | Eli Lilly And Company | Fluoropyridyl pyrazol compounds |
| EP3412658A1 (en) * | 2017-06-09 | 2018-12-12 | Solvay Sa | Processes for the manufacture of sulfur-substitued pyrazole derivatives |
| EP4253380A3 (en) * | 2019-10-18 | 2023-11-15 | FMC Corporation | Methods for the preparation of 5-bromo-2-(3-chloro-pyridin-2-yl)-2h-pyrazole-3-carboxylic acid |
| JP2022552276A (ja) * | 2019-10-18 | 2022-12-15 | エフ エム シー コーポレーション | ５－ブロモ－２－（３－クロロ－ピリジン－２－イル）－２ｈ－ピラゾール－３－カルボン酸の調製方法 |
| TW202241859A (zh) * | 2021-01-29 | 2022-11-01 | 美商富曼西公司 | 用於製備５－溴－２－（３－氯－吡啶－２－基）－２ｈ－吡唑－３－甲酸之方法 |
| CN120500474A (zh) * | 2023-01-09 | 2025-08-15 | 弗陆创新有限公司 | 制备3-卤甲基取代的1-甲基-1h-吡唑-4-碳腈及其衍生物及其中间体的新方法 |
| CN116606263B (zh) * | 2023-05-26 | 2025-06-13 | 青岛科技大学 | 一种含氟苯联噻唑双酯类化合物及其用途 |
| WO2025168620A1 (en) * | 2024-02-07 | 2025-08-14 | Bayer Aktiengesellschaft | Heteroaryl-substituted 4,5-dihydro-1h-2,4,5-oxadiazines as novel fungicides |
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| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| JPS5527916B2 (enExample) * | 1973-02-05 | 1980-07-24 | ||
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-
2011
- 2011-08-26 TW TW100130635A patent/TW201245155A/zh unknown
- 2011-08-31 EP EP11757463.2A patent/EP2611297B1/en not_active Not-in-force
- 2011-08-31 AU AU2011295998A patent/AU2011295998A1/en not_active Abandoned
- 2011-08-31 PL PL11757463T patent/PL2611297T3/pl unknown
- 2011-08-31 CN CN201510578968.7A patent/CN105130900B/zh not_active Expired - Fee Related
- 2011-08-31 UY UY33582A patent/UY33582A/es not_active Application Discontinuation
- 2011-08-31 KR KR20137008060A patent/KR20130139892A/ko not_active Withdrawn
- 2011-08-31 JP JP2013527253A patent/JP6066910B2/ja not_active Expired - Fee Related
- 2011-08-31 MX MX2013002400A patent/MX2013002400A/es not_active Application Discontinuation
- 2011-08-31 BR BR122017015898-8A patent/BR122017015898B1/pt not_active IP Right Cessation
- 2011-08-31 ES ES11757463.2T patent/ES2546671T3/es active Active
- 2011-08-31 US US13/816,847 patent/US8754115B2/en not_active Expired - Fee Related
- 2011-08-31 BR BR112013004835-2A patent/BR112013004835B1/pt not_active IP Right Cessation
- 2011-08-31 CN CN201180042397.5A patent/CN103079406B/zh not_active Expired - Fee Related
- 2011-08-31 WO PCT/US2011/049908 patent/WO2012030922A1/en not_active Ceased
- 2011-09-01 AR ARP110103199 patent/AR082869A1/es unknown
-
2014
- 2014-04-10 US US14/249,658 patent/US9131693B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR122017015898B1 (pt) | 2018-05-15 |
| AR082869A1 (es) | 2013-01-16 |
| ES2546671T3 (es) | 2015-09-25 |
| CN103079406A (zh) | 2013-05-01 |
| UY33582A (es) | 2012-03-30 |
| AU2011295998A1 (en) | 2013-02-21 |
| US20140221448A1 (en) | 2014-08-07 |
| BR112013004835B1 (pt) | 2018-01-09 |
| BR112013004835A2 (pt) | 2016-05-31 |
| JP2013536856A (ja) | 2013-09-26 |
| PL2611297T3 (pl) | 2015-11-30 |
| EP2611297A1 (en) | 2013-07-10 |
| US20130143940A1 (en) | 2013-06-06 |
| WO2012030922A1 (en) | 2012-03-08 |
| CN105130900B (zh) | 2018-05-22 |
| TW201245155A (en) | 2012-11-16 |
| CN105130900A (zh) | 2015-12-09 |
| US8754115B2 (en) | 2014-06-17 |
| JP6066910B2 (ja) | 2017-01-25 |
| EP2611297B1 (en) | 2015-06-17 |
| CN103079406B (zh) | 2016-03-30 |
| KR20130139892A (ko) | 2013-12-23 |
| US9131693B2 (en) | 2015-09-15 |
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| FA | Abandonment or withdrawal |