CA2854100A1 - Substituted 1,2,5-oxadiazole compounds and their use as herbicides iii - Google Patents
Substituted 1,2,5-oxadiazole compounds and their use as herbicides iii Download PDFInfo
- Publication number
- CA2854100A1 CA2854100A1 CA2854100A CA2854100A CA2854100A1 CA 2854100 A1 CA2854100 A1 CA 2854100A1 CA 2854100 A CA2854100 A CA 2854100A CA 2854100 A CA2854100 A CA 2854100A CA 2854100 A1 CA2854100 A1 CA 2854100A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkoxy
- group
- haloalkyl
- halogen
- 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
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- 150000002244 furazanes Chemical class 0.000 title abstract description 9
- 239000004009 herbicide Substances 0.000 title description 40
- -1 Z2-cyano Chemical group 0.000 claims abstract description 482
- 150000001875 compounds Chemical class 0.000 claims abstract description 432
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 188
- 150000002367 halogens Chemical class 0.000 claims abstract description 187
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 149
- 239000001257 hydrogen Substances 0.000 claims abstract description 131
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 111
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 53
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 43
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 33
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims abstract description 32
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 29
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 20
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 5
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims abstract description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 245
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 198
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 91
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 150000003254 radicals Chemical class 0.000 claims description 73
- 229910052757 nitrogen Inorganic materials 0.000 claims description 68
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 52
- 125000005842 heteroatom Chemical group 0.000 claims description 50
- 229910052717 sulfur Inorganic materials 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 45
- 229920006395 saturated elastomer Polymers 0.000 claims description 43
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 40
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 33
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 33
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 33
- 125000002950 monocyclic group Chemical group 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 150000001204 N-oxides Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002619 bicyclic group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 2
- 235000013350 formula milk Nutrition 0.000 description 218
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 143
- 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 description 142
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 description 142
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 135
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 111
- 239000005562 Glyphosate Substances 0.000 description 101
- 239000000460 chlorine Substances 0.000 description 87
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 87
- 229940097068 glyphosate Drugs 0.000 description 87
- 239000005591 Pendimethalin Substances 0.000 description 67
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 67
- 150000002148 esters Chemical class 0.000 description 50
- 239000005507 Diflufenican Substances 0.000 description 49
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 49
- 239000005621 Terbuthylazine Substances 0.000 description 47
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 47
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 43
- 125000004432 carbon atom Chemical group C* 0.000 description 43
- 229910052801 chlorine Inorganic materials 0.000 description 38
- 230000002363 herbicidal effect Effects 0.000 description 38
- 239000005580 Metazachlor Substances 0.000 description 37
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 37
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 32
- 239000005578 Mesotrione Substances 0.000 description 28
- 239000005586 Nicosulfuron Substances 0.000 description 28
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 28
- 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 28
- 229910052794 bromium Inorganic materials 0.000 description 27
- 239000005620 Tembotrione Substances 0.000 description 25
- 244000038559 crop plants Species 0.000 description 25
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 25
- 239000003053 toxin Substances 0.000 description 23
- 231100000765 toxin Toxicity 0.000 description 23
- 108700012359 toxins Proteins 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- 239000005597 Pinoxaden Substances 0.000 description 18
- 239000005607 Pyroxsulam Substances 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 18
- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 description 18
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 18
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 18
- 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 17
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 17
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 17
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 17
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 16
- 239000011737 fluorine Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 108090000623 proteins and genes Proteins 0.000 description 15
- 229910052702 rhenium Inorganic materials 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- RUCAXVJJQQJZGU-UHFFFAOYSA-M hydron;2-(phosphonatomethylamino)acetate;trimethylsulfanium Chemical compound C[S+](C)C.OP(O)(=O)CNCC([O-])=O RUCAXVJJQQJZGU-UHFFFAOYSA-M 0.000 description 14
- PVSGXWMWNRGTKE-UHFFFAOYSA-N 5-methyl-2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=C(C)C=C1C(O)=O PVSGXWMWNRGTKE-UHFFFAOYSA-N 0.000 description 13
- 239000005499 Clomazone Substances 0.000 description 13
- 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 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 240000008042 Zea mays Species 0.000 description 13
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 13
- 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 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- 239000005560 Foramsulfuron Substances 0.000 description 12
- 239000005583 Metribuzin Substances 0.000 description 12
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
- 235000005822 corn Nutrition 0.000 description 12
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 12
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 12
- 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 12
- 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 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 229910052703 rhodium Inorganic materials 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 10
- 239000005561 Glufosinate Substances 0.000 description 10
- 241000219146 Gossypium Species 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
- 150000003852 triazoles Chemical class 0.000 description 10
- 235000002595 Solanum tuberosum Nutrition 0.000 description 9
- 244000061456 Solanum tuberosum Species 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
- 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 description 8
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000005566 Imazamox Substances 0.000 description 8
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 238000010353 genetic engineering Methods 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 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 8
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 8
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 7
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 7
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 7
- MAYMYMXYWIVVOK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(CNS(C)(=O)=O)C=2)C(O)=O)=N1 MAYMYMXYWIVVOK-UHFFFAOYSA-N 0.000 description 7
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 7
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- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- 125000004275 thietan-2-yl group Chemical group [H]C1([H])SC([H])(*)C1([H])[H] 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000004569 thiomorpholin-2-yl group Chemical group N1CC(SCC1)* 0.000 description 1
- 125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-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
- 238000001665 trituration Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 150000004669 very long chain fatty acids Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161561324P | 2011-11-18 | 2011-11-18 | |
| US61/561,324 | 2011-11-18 | ||
| PCT/EP2012/072810 WO2013072450A1 (en) | 2011-11-18 | 2012-11-16 | Substituted 1,2,5-oxadiazole compounds and their use as herbicides iii |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2854100A1 true CA2854100A1 (en) | 2013-05-23 |
Family
ID=47189941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2854100A Abandoned CA2854100A1 (en) | 2011-11-18 | 2012-11-16 | Substituted 1,2,5-oxadiazole compounds and their use as herbicides iii |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20140309115A1 (https=) |
| EP (1) | EP2780340A1 (https=) |
| JP (1) | JP2015502927A (https=) |
| KR (1) | KR20140107280A (https=) |
| CN (1) | CN104039780A (https=) |
| AR (1) | AR090397A1 (https=) |
| AU (1) | AU2012338748A1 (https=) |
| BR (1) | BR112014011685A2 (https=) |
| CA (1) | CA2854100A1 (https=) |
| CO (1) | CO6950501A2 (https=) |
| CR (1) | CR20140218A (https=) |
| IL (1) | IL232468A0 (https=) |
| IN (1) | IN2014CN03480A (https=) |
| WO (1) | WO2013072450A1 (https=) |
| ZA (1) | ZA201404331B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103459386B (zh) * | 2011-03-15 | 2016-06-22 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)吡啶甲酰胺及其作为除草剂的用途 |
| CN103429578B (zh) * | 2011-03-15 | 2016-06-01 | 拜耳知识产权有限责任公司 | 除草剂安全剂组合物 |
| CN104053656A (zh) | 2011-11-16 | 2014-09-17 | 巴斯夫欧洲公司 | 取代的1,2,5-噁二唑化合物及其作为除草剂的用途ii |
| KR101982620B1 (ko) | 2013-02-26 | 2019-05-27 | 타츠타 전선 주식회사 | 플렉시블 프린트 배선판용 보강 부재, 플렉시블 프린트 배선판, 및 차폐 프린트 배선판 |
| WO2014184014A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | N-(1,2,5-oxadiazol-3-yl)carboxamide compounds and their use as herbicides |
| MY172600A (en) | 2013-05-31 | 2019-12-05 | Nissan Chemical Ind Ltd | Heterocyclic amide compound |
| WO2015052178A1 (en) * | 2013-10-10 | 2015-04-16 | Basf Se | 1,2,5-oxadiazole compounds and their use as herbicides |
| WO2015052152A1 (en) * | 2013-10-10 | 2015-04-16 | Basf Se | Substituted 1,2,5-oxadiazole compounds and their use as herbicides |
| AR101230A1 (es) * | 2014-07-28 | 2016-11-30 | Bayer Cropscience Ag | Amidas del ácido arilcarboxílico bicíclicas y su uso como herbicidas |
| BR112018004779A8 (pt) | 2015-09-11 | 2022-08-09 | Bayer Cropscience Lp | Variantes de hppd e métodos de uso |
| CA3055389A1 (en) | 2017-03-07 | 2018-09-13 | BASF Agricultural Solutions Seed US LLC | Hppd variants and methods of use |
| CN112624989B (zh) * | 2019-10-08 | 2024-01-26 | 沈阳中化农药化工研发有限公司 | 一种酰胺类化合物及其应用 |
| CN115768752B (zh) * | 2020-04-07 | 2025-04-22 | 拜耳公司 | 取代的间苯二酸二酰胺 |
| US11772496B2 (en) | 2020-08-26 | 2023-10-03 | Anusheel Nahar | Regenerative braking system of an automobile and a method to operate |
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| IT1196237B (it) * | 1984-08-29 | 1988-11-16 | Enichimica Secondaria | Composti eterociclici ad attivita' erbicida |
| BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
| ATE57390T1 (de) | 1986-03-11 | 1990-10-15 | Plant Genetic Systems Nv | Durch gentechnologie erhaltene und gegen glutaminsynthetase-inhibitoren resistente pflanzenzellen. |
| US5013659A (en) | 1987-07-27 | 1991-05-07 | E. I. Du Pont De Nemours And Company | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| IL83348A (en) | 1986-08-26 | 1995-12-08 | Du Pont | Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase |
| CA1340284C (en) | 1987-03-19 | 1998-12-22 | Zeneca Inc. | Herbicidal substituted cyclic diones |
| EP0316491A1 (en) | 1987-11-19 | 1989-05-24 | Stauffer Agricultural Chemicals Company, Inc. | Herbicidal 2-pyridyl and 2-pyrimidine carbonyl 1,3-cyclohexanediones |
| FR2629098B1 (fr) | 1988-03-23 | 1990-08-10 | Rhone Poulenc Agrochimie | Gene chimerique de resistance herbicide |
| EP0374753A3 (de) | 1988-12-19 | 1991-05-29 | American Cyanamid Company | Insektizide Toxine, Gene, die diese Toxine kodieren, Antikörper, die sie binden, sowie transgene Pflanzenzellen und transgene Pflanzen, die diese Toxine exprimieren |
| DK0392225T3 (da) | 1989-03-24 | 2003-09-22 | Syngenta Participations Ag | Sygdomsresistente transgene planter |
| EP0427529B1 (en) | 1989-11-07 | 1995-04-19 | Pioneer Hi-Bred International, Inc. | Larvicidal lectins and plant insect resistance based thereon |
| JP3173784B2 (ja) | 1990-06-25 | 2001-06-04 | モンサント カンパニー | グリホセート耐性植物 |
| UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
| JPH05117255A (ja) * | 1991-10-25 | 1993-05-14 | Nippon Soda Co Ltd | オキサジアゾール及びチアジアゾール誘導体、その製法 |
| US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
| DE19505995A1 (de) | 1995-02-21 | 1996-08-22 | Degussa | Verfahren zur Herstellung von Thietanonen |
| WO1997041116A1 (en) | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Benzene derivatives substituted by heterocycles and herbicides |
| BR9708828A (pt) | 1996-04-26 | 1999-08-03 | Nippon Soda Co | Composto e composição herbicida |
| WO1997041117A1 (en) | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Novel benzene derivatives substituted by heterocycles and herbicides |
| US5773704A (en) | 1996-04-29 | 1998-06-30 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Herbicide resistant rice |
| SK286030B6 (sk) | 1996-07-17 | 2008-01-07 | Michigan State University | Rastlinný materiál cukrovej repy rezistentnej voči herbicídom, spôsob produkcie herbicídne rezistentnej rastliny cukrovej repy a spôsob kontroly burín v prítomnosti týchto rastlín |
| US5773702A (en) | 1996-07-17 | 1998-06-30 | Board Of Trustees Operating Michigan State University | Imidazolinone herbicide resistant sugar beet plants |
| US6348643B1 (en) | 1998-10-29 | 2002-02-19 | American Cyanamid Company | DNA sequences encoding the arabidopsis acetohydroxy-acid synthase small subunit and methods of use |
| CA2353627C (en) * | 1998-11-04 | 2010-10-26 | Keiichi Imamura | Picolinamide derivative and harmful organism control agent comprising said picolinamide derivative as active component |
| AR023071A1 (es) | 1998-12-23 | 2002-09-04 | Syngenta Participations Ag | Compuestos de piridincetona, compuestos intermediarios, composicion herbicida e inhibidora del crecimiento de plantas, metodo para controlar la vegetacion indeseada, metodo para inhibir el crecimiento de las plantas, y uso de la composicion para controlar el crecimiento indeseado de plantas. |
| AU5920601A (en) | 2000-04-28 | 2001-11-12 | American Cyanamid Co | Use of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides |
| HU229494B1 (en) | 2000-05-04 | 2014-01-28 | Basf Ag | Uracil substituted phenyl sulfamoyl carboxamides |
| AU8590001A (en) | 2000-08-25 | 2002-03-04 | Syngenta Participations Ag | Novel insecticidal toxins derived from bacillus thuringiensis insecticidal crystal proteins |
| WO2003014356A1 (en) | 2001-08-09 | 2003-02-20 | University Of Saskatchewan | Wheat plants having increased resistance to imidazolinone herbicides |
| EP1414975B1 (en) | 2001-08-09 | 2016-04-20 | University Of Saskatchewan | Wheat plants having increased resistance to imidazolinone herbicides |
| US7528297B2 (en) | 2001-08-09 | 2009-05-05 | Northwest Plant Breeding Company | Wheat plants having increased resistance to imidazolinone herbicides |
| US7230167B2 (en) | 2001-08-31 | 2007-06-12 | Syngenta Participations Ag | Modified Cry3A toxins and nucleic acid sequences coding therefor |
| WO2003052073A2 (en) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Novel corn event |
| CA2492167C (en) | 2002-07-10 | 2015-06-16 | The Department Of Agriculture, Western Australia | Wheat plants having increased resistance to imidazolinone herbicides |
| US9382526B2 (en) | 2003-05-28 | 2016-07-05 | Basf Aktiengesellschaft | Wheat plants having increased tolerance to imidazolinone herbicides |
| BRPI0413917B1 (pt) | 2003-08-29 | 2018-09-25 | Instituto Nacional De Tech Agropecuaria | ácido nucleico ahas de arroz mutagenizado não transgênico, polipeptídeo ahas isolado, e, método de controle de ervas daninhas dentro da vizinhança de uma planta de arroz |
| PL1879573T3 (pl) * | 2005-05-10 | 2013-05-31 | Incyte Holdings Corp | Modulatory 2,3-dioksygenazy indoloaminy i sposoby ich zastosowania |
| GB0625598D0 (en) | 2006-12-21 | 2007-01-31 | Syngenta Ltd | Novel herbicides |
| GB0805318D0 (en) | 2008-03-20 | 2008-04-30 | Syngenta Ltd | Herbicidal compounds |
| CN102639517B (zh) * | 2009-09-25 | 2016-05-11 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)苯甲酰胺及其作为除草剂的用途 |
| CN103429578B (zh) * | 2011-03-15 | 2016-06-01 | 拜耳知识产权有限责任公司 | 除草剂安全剂组合物 |
| CN103459386B (zh) * | 2011-03-15 | 2016-06-22 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)吡啶甲酰胺及其作为除草剂的用途 |
-
2012
- 2012-11-16 KR KR1020147016744A patent/KR20140107280A/ko not_active Withdrawn
- 2012-11-16 JP JP2014541676A patent/JP2015502927A/ja active Pending
- 2012-11-16 WO PCT/EP2012/072810 patent/WO2013072450A1/en not_active Ceased
- 2012-11-16 US US14/357,899 patent/US20140309115A1/en not_active Abandoned
- 2012-11-16 AU AU2012338748A patent/AU2012338748A1/en not_active Abandoned
- 2012-11-16 BR BR112014011685A patent/BR112014011685A2/pt not_active IP Right Cessation
- 2012-11-16 AR ARP120104330A patent/AR090397A1/es not_active Application Discontinuation
- 2012-11-16 CA CA2854100A patent/CA2854100A1/en not_active Abandoned
- 2012-11-16 CN CN201280067028.6A patent/CN104039780A/zh active Pending
- 2012-11-16 EP EP12787442.8A patent/EP2780340A1/en not_active Withdrawn
- 2012-11-16 IN IN3480CHN2014 patent/IN2014CN03480A/en unknown
-
2014
- 2014-05-05 IL IL232468A patent/IL232468A0/en unknown
- 2014-05-09 CO CO14100202A patent/CO6950501A2/es not_active Application Discontinuation
- 2014-05-12 CR CR20140218A patent/CR20140218A/es unknown
- 2014-06-13 ZA ZA2014/04331A patent/ZA201404331B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CR20140218A (es) | 2014-06-19 |
| EP2780340A1 (en) | 2014-09-24 |
| BR112014011685A2 (pt) | 2017-05-30 |
| ZA201404331B (en) | 2016-10-26 |
| IN2014CN03480A (https=) | 2015-07-03 |
| WO2013072450A1 (en) | 2013-05-23 |
| AU2012338748A1 (en) | 2014-06-05 |
| IL232468A0 (en) | 2014-06-30 |
| AR090397A1 (es) | 2014-11-12 |
| US20140309115A1 (en) | 2014-10-16 |
| CN104039780A (zh) | 2014-09-10 |
| KR20140107280A (ko) | 2014-09-04 |
| CO6950501A2 (es) | 2014-05-20 |
| JP2015502927A (ja) | 2015-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20151117 |