EP2571364A1 - Agents herbicides pour cultures de riz tolérantes ou résistantes - Google Patents
Agents herbicides pour cultures de riz tolérantes ou résistantesInfo
- Publication number
- EP2571364A1 EP2571364A1 EP11720485A EP11720485A EP2571364A1 EP 2571364 A1 EP2571364 A1 EP 2571364A1 EP 11720485 A EP11720485 A EP 11720485A EP 11720485 A EP11720485 A EP 11720485A EP 2571364 A1 EP2571364 A1 EP 2571364A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- chloro
- fluoro
- methoxyphenyl
- amino
- carboxylic acid
- 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.)
- Withdrawn
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 81
- 235000007164 Oryza sativa Nutrition 0.000 title claims abstract description 41
- 235000009566 rice Nutrition 0.000 title claims abstract description 41
- 240000007594 Oryza sativa Species 0.000 title description 39
- 241000196324 Embryophyta Species 0.000 claims abstract description 101
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 241000209094 Oryza Species 0.000 claims abstract 6
- 239000004480 active ingredient Substances 0.000 claims description 59
- -1 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid allyl ester Chemical class 0.000 claims description 50
- 239000005562 Glyphosate Substances 0.000 claims description 15
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 9
- 229940097068 glyphosate Drugs 0.000 claims description 9
- KMQMZLQGLPHAOQ-UHFFFAOYSA-N 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)N=2)C(O)=O)=C1F KMQMZLQGLPHAOQ-UHFFFAOYSA-N 0.000 claims description 7
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 7
- ROBSGBGTWRRYSK-SNVBAGLBSA-N (2r)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CC=C(C#N)C=C1F ROBSGBGTWRRYSK-SNVBAGLBSA-N 0.000 claims description 6
- UFAPVJDEYHLLBG-UHFFFAOYSA-N 2-{2-chloro-4-(methylsulfonyl)-3-[(tetrahydrofuran-2-ylmethoxy)methyl]benzoyl}cyclohexane-1,3-dione Chemical compound ClC1=C(COCC2OCCC2)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O UFAPVJDEYHLLBG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 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 claims description 6
- CLQREWNDDSMAPG-UHFFFAOYSA-N methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 CLQREWNDDSMAPG-UHFFFAOYSA-N 0.000 claims description 6
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 5
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 5
- 239000005499 Clomazone Substances 0.000 claims description 5
- 239000005504 Dicamba Substances 0.000 claims description 5
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 5
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 5
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 5
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 5
- KKLBEFSLWYDQFI-UHFFFAOYSA-N halauxifen Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C(O)=O)=C1F KKLBEFSLWYDQFI-UHFFFAOYSA-N 0.000 claims description 5
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002917 insecticide Substances 0.000 claims description 5
- LIOPHZNMBKHGAV-UHFFFAOYSA-M potassium;2-(phosphonomethylamino)acetate Chemical compound [K+].OC(=O)CNCP(O)([O-])=O LIOPHZNMBKHGAV-UHFFFAOYSA-M 0.000 claims description 5
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 5
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1r,5s)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 claims description 4
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 claims description 4
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 claims description 4
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005472 Bensulfuron methyl Substances 0.000 claims description 4
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 4
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 4
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 4
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 4
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 claims description 4
- LLQPHQFNMLZJMP-UHFFFAOYSA-N Fentrazamide Chemical compound N1=NN(C=2C(=CC=CC=2)Cl)C(=O)N1C(=O)N(CC)C1CCCCC1 LLQPHQFNMLZJMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005531 Flufenacet Substances 0.000 claims description 4
- 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 claims description 4
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 4
- 239000005591 Pendimethalin Substances 0.000 claims description 4
- 239000005592 Penoxsulam Substances 0.000 claims description 4
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 claims description 4
- IHHMUBRVTJMLQO-UHFFFAOYSA-N Pyraclonil Chemical compound C#CCN(C)C1=C(C#N)C=NN1C1=NN(CCCC2)C2=C1Cl IHHMUBRVTJMLQO-UHFFFAOYSA-N 0.000 claims description 4
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 claims description 4
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 4
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000005648 plant growth regulator Substances 0.000 claims description 4
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims description 4
- MPPOHAUSNPTFAJ-SECBINFHSA-N (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-SECBINFHSA-N 0.000 claims description 3
- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 claims description 3
- QNOYASBPPVBWOG-UHFFFAOYSA-N 2-butoxyethyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCOCCCC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 QNOYASBPPVBWOG-UHFFFAOYSA-N 0.000 claims description 3
- RJNIVVXIMPAOJR-UHFFFAOYSA-N 2-butoxyethyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCOCCCC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 RJNIVVXIMPAOJR-UHFFFAOYSA-N 0.000 claims description 3
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005476 Bentazone Substances 0.000 claims description 3
- JDWQITFHZOBBFE-UHFFFAOYSA-N Benzofenap Chemical compound C=1C=C(Cl)C(C)=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=C(C)C=C1 JDWQITFHZOBBFE-UHFFFAOYSA-N 0.000 claims description 3
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims description 3
- 239000005513 Fenoxaprop-P Substances 0.000 claims description 3
- FICWGWVVIRLNRB-UHFFFAOYSA-N Flucetosulfuron Chemical compound COCC(=O)OC(C(C)F)C1=NC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 FICWGWVVIRLNRB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005566 Imazamox Substances 0.000 claims description 3
- 239000005567 Imazosulfuron Substances 0.000 claims description 3
- NAGRVUXEKKZNHT-UHFFFAOYSA-N Imazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N3C=CC=CC3=NC=2Cl)=N1 NAGRVUXEKKZNHT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005574 MCPA Substances 0.000 claims description 3
- 239000005586 Nicosulfuron Substances 0.000 claims description 3
- 239000005587 Oryzalin Substances 0.000 claims description 3
- 239000005589 Oxasulfuron Substances 0.000 claims description 3
- 239000005607 Pyroxsulam Substances 0.000 claims description 3
- 239000005622 Thiencarbazone Substances 0.000 claims description 3
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 3
- 239000005629 Tritosulfuron Substances 0.000 claims description 3
- QRSHQJLLXXEYPS-UHFFFAOYSA-N azane;5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)pyridine-3-carboxylic acid Chemical compound [NH4+].[O-]C(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 QRSHQJLLXXEYPS-UHFFFAOYSA-N 0.000 claims description 3
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 claims description 3
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 3
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 3
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 claims description 3
- SGXWIMKOKXLUJB-UHFFFAOYSA-N butan-2-yl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC(C)CC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 SGXWIMKOKXLUJB-UHFFFAOYSA-N 0.000 claims description 3
- CPHCYTUHSKEDOI-UHFFFAOYSA-N diazanium;2-(phosphonatomethylamino)acetic acid Chemical compound [NH4+].[NH4+].OC(=O)CNCP([O-])([O-])=O CPHCYTUHSKEDOI-UHFFFAOYSA-N 0.000 claims description 3
- AVTOKORLWSVVBY-UHFFFAOYSA-N ethyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 AVTOKORLWSVVBY-UHFFFAOYSA-N 0.000 claims description 3
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 claims description 3
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 claims description 3
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 claims description 3
- XZJWUCZWEDFYJH-UHFFFAOYSA-M potassium;4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate Chemical compound [K+].COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C([O-])=O)=C1F XZJWUCZWEDFYJH-UHFFFAOYSA-M 0.000 claims description 3
- PALNQVGMNSDXPI-UHFFFAOYSA-N propan-2-yl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C(=O)OC(C)C)=C1F PALNQVGMNSDXPI-UHFFFAOYSA-N 0.000 claims description 3
- YTTCSGUYLRIAAR-UHFFFAOYSA-N propyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 YTTCSGUYLRIAAR-UHFFFAOYSA-N 0.000 claims description 3
- LUJHPOIWXKGMNL-UHFFFAOYSA-N propyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCCC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 LUJHPOIWXKGMNL-UHFFFAOYSA-N 0.000 claims description 3
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- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Definitions
- the invention is in the field of pesticides which can be used against harmful plants in tolerant or resistant crops of rice and contain as herbicidal active ingredients a combination of two or more herbicides.
- the effectiveness of these herbicides against harmful plants in the tolerant crops is at a high level, but depends - similar to other herbicides - on the type of herbicide used, its application rate, the particular formulation, each to be controlled harmful plant stages, climate and soil conditions , etc. from. Furthermore, the herbicides have weaknesses (gaps) against specific types of harmful plants. Another criterion is the duration of the action or the degradation rate of the herbicide. It may also be necessary to take account of changes in the susceptibility of harmful plants, which may occur with prolonged use of the herbicides or geographically. Losses of activity in individual plant species can be only partially, if at all, offset by higher application rates of herbicides.
- a lower application rate not only reduces the amount of an active ingredient required for the application, but also reduces the amount as a rule on necessary formulation aids. Both reduce the economic effort and improve the environmental compatibility of the herbicide treatment.
- One way to improve the application profile of a herbicide may be to combine the active ingredient with one or more other agents that provide the desired additional properties.
- phenomena of chemical, physical and biological incompatibility often occur in the combined use of several active ingredients, eg. B. lack of stability of a coformulation, decomposition of an active ingredient or antagonism in the biological activity of the active ingredients.
- Desired, however, are combinations of active ingredients with favorable effect profile, high stability and synergistically enhanced as possible effect, which allows a reduction in the application rate compared to the single application of the active ingredients to be combined.
- the compounds (A) and (B) are known. Compounds of type (A1) are described, for example, in DE-A 271 7440.
- WO 2007/1 20706 discloses synergistic herbicidal combinations which contain a pyrimidine carboxylic acid of formula 1 and a second herbicide or herbicide safener,
- US-A-2002/094934 discloses herbicide combinations containing a herbicide A (see p. 1, A. 6-14) and a herbicide B (see pp. 1-2, A. 15-19).
- US-A-2007/179059 discloses pyrimidinecarboxylic acids and their derivatives of the formula L. Surprisingly, it has now been found that certain active ingredients from the group of said broad-spectrum herbicides (A) in combination with certain herbicides (B) in a particularly favorable (synergistic) way cooperate when used in the rice crops, which are used for the selective application of the former Herbicides are suitable.
- the invention thus relates to the use of herbicide combinations for combating harmful plants in rice crops, characterized in that the respective herbicide combination comprises a herbicide from the group of the compounds of the formula (A1),
- Z is hydroxy, -NHCH (CH 3 ) CONHCH (CH 3 ) COOH -NHCH (CH 3 ) CONHCH [CH 2 CH (CH 3 ) 2 ] COOH, or its ester or salts, and
- X is N or CH and R is C0 2 H or a herbicidally active derivative
- the rice crops are tolerant to the herbicides (A) and (B) contained in the combination, optionally in the presence of safeners.
- a herbicidally active derivative is salts, esters, carboxamides, acylhydrazides, imidates, thioimidates, amidines, acyl halides, Acyl cyanides, acid anhydrides, ethers, acetals, orthoesters, carboxaldehydes, oximes, hydrazones, thioacids, thioesters, dithiol esters, nitriles and any other carboxylic acid derivative which does not quench the herbicidal activity of the compound of general formula (B1) and in plants and / or in Soil, for example, by hydrolysis, oxidation, reductive or other Meta bol is ieru
- the compounds of formula (B1) may further form salts by addition of a suitable inorganic or organic acid such as HCl, HBr, H 2 SO 4 or HNO 3 , but also oxalic acid or sulfonic acids to a basic group such as amino or alkylamino , Suitable substituents which are present in deprotonated form, such as, for example, sulfonic acids or carboxylic acids, can form internal salts with groups which can themselves be protonated, such as amino groups. Salts can also be formed by replacing the hydrogen with a suitable cation for agriculture with suitable substituents, such as, for example, sulfonic acids or carboxylic acids.
- salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts with cations of the formula [NRR'R "R"'] + , wherein R to R '"each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
- the compounds of general formula (B1) may also include N-oxides.
- Corresponding pyridine-N-oxides are available as pure oxide at the corresponding pyridine ion.
- Appropriate oxidation methods are, for example, in Houben-Weyl, Methods of Organic Chemistry, Extension and following volumes to the 4th edition, Volume E 7b, p 565 f. described.
- Preferred as component (B) in each case are: 4-Amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid (B1 .0)
- 6-Amino-5-chloro-2- (4-chloro-2-fluoro-3-methoxyphenyl) pyrimidine-4-carboxylic acid 2-butoxyethyl ester (B1 .21) 6-Amino-5-chloro-2- (4-chloro-2-fluoro-3-methoxyphenyl) pyrimidine-4-carbon triethylammonium salt (B1 .22) - 6-Amino-5-chloro-2- (4-chloro) 2-fluoro-3-methoxyphenyl) pyrimidine-4-carboxylic acid 2-butoxyethyl ester (B1 .21) 6-Amino-5-chloro-2- (4-chloro-2-fluoro-3-methoxyphenyl) pyrimidine-4-carbon triethylammonium salt (B1 .22) - 6-Amino-5-chloro-2- (4-chloro) 2-fluoro-3-methoxyphenyl)
- Particularly preferred components (B) are - 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid (B1 .0) and
- the synergistic effects are observed when the active ingredients (A) and (B) are applied together, but they can also be detected by splitting. It is also possible to use the herbicides or herbicide combinations in several portions (sequence application), eg. After pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the simultaneous use of the active ingredients of the respective combination, optionally in several portions. But also the delayed use of the individual active ingredients of a combination is possible and may be advantageous in individual cases. In this system application, other crop protection agents such as fungicides, insecticides, acaricides, etc. and / or various adjuvants, adjuvants and / or fertilizers can be integrated.
- other crop protection agents such as fungicides, insecticides, acaricides, etc. and / or various adjuvants, adjuvants and / or fertilizers can be integrated.
- the synergistic effects allow a reduction in the application rates of the individual active ingredients, a higher potency against the same harmful plant species at the same rate, the control of previously unrecognized species (gaps), an extension of the period of application and / or a reduction in the number of necessary individual applications and - as a result for the Users - economically and ecologically more advantageous weed control systems.
- herbicide combinations are provided which can be used particularly favorably in tolerant rice crops.
- the herbicides mentioned (A1 .1) to (A1 .3) are taken up via the green parts of the plants and are known as broad-spectrum herbicides or total herbicides; they are inhibitors of the enzyme glutamine synthetase in plants; See "The Pesticide Manual” 11 edition, British Crop Protection Council 1997, pp. 643-645 and 120-121, respectively.
- the combinations are suitably used in rice cultures which are tolerant to the compounds (A1). The tolerance may have been generated by breeding or mutation selection (eg analogously to the commercially available Clearfield® rice cultures from BASF, which are tolerant to imidazolinone herbicides), or by genetic engineering.
- the application rates of the herbicides (B) can vary widely. The following ranges are useful: Generally 2.5-500 g AS / ha, preferably 4 to 400 g AS / ha, more preferably 5-250 g AS / ha (see the details of the group of compounds (A)
- additives for example, fertilizers, ionic / nonionic wetting agents, oil and dyes.
- those combinations according to the invention which also contain one or more further active compounds of other structure [active ingredients (C)], for example safeners, plant growth regulators or other herbicides.
- active ingredients (C) for example safeners, plant growth regulators or other herbicides.
- active ingredients (B) and (C) for example safeners, plant growth regulators or other herbicides.
- active ingredient (C) Particularly suitable as active ingredient (C) are the safeners cyprosulfamides (C1), isoxadifen (-ethyl) (C2) and mefenpyr (-diethyl) (C3). Also particularly suitable as active compound (C) are the active substances anilofos (C4), azimosulfuron (C5), benfuresate (C6), bensulfuron (C7), bensulfuron-methyl (C8), bentazone (C9), benzofenap (C10), bicyclopyrone (C10).
- Anilofos (C4), benfuresates (C6), bensulfuron-methyl (C8), carfentrazone-ethyl (C14), clomazone (C17), clomeprop (C18), cyhalofop (C19), 2, are particularly suitable as active compound (C).
- A1.1 B1.12 C6 A1.1 B1.12 C72 WirkWirkWirkWirkWirkAbjective (A) fabric (B) fabric (C) fabric (A) fabric (B) fabric (C)
- A1.2 B1.1 C14 A1.2 B1.2 C6 WirkWirkWirkWirkWirkAbjective (A) fabric (B) fabric (C) fabric (A) fabric (B) fabric (C)
- A1.2 B1.16 C6 A1.2 B1.16 C72 WirkWirkWirkWirkWirkAbjective (A) fabric (B) fabric (C) fabric (A) fabric (B) fabric (C)
- A1.2 B1.21 C50 A1.2 B1.22 C44 WirkWirkWirkWirkWirkAbjective (A) fabric (B) fabric (C) fabric (A) fabric (B) fabric (C)
Landscapes
- 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)
Abstract
L'invention concerne des associations d'herbicides et l'utilisation d'associations d'herbicides pour la lutte contre les plantes nuisibles dans les cultures de riz. L'invention est caractérisée en ce que l'association d'herbicides concernée contient (A) un herbicide du groupe des composés de formule (A1), dans laquelle Z désigne hydroxy, -NHCH(CH3)CONHCH(CH3)COOH ou -NHCH(CH3)CONHCH[CH2CH(CH3)2]COOH, ou bien ses esters ou sels, et (B) un herbicide de formule (B1), dans laquelle X représente N ou CH et R désigne CO2H ou un dérivé à action herbicide, et les cultures de riz sont tolérantes aux herbicides (A) et (B) contenus dans l'association, éventuellement en présence de phytoprotecteurs.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11720485A EP2571364A1 (fr) | 2010-05-21 | 2011-05-19 | Agents herbicides pour cultures de riz tolérantes ou résistantes |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10163615 | 2010-05-21 | ||
PCT/EP2011/058107 WO2011144684A1 (fr) | 2010-05-21 | 2011-05-19 | Agents herbicides pour cultures de riz tolérantes ou résistantes |
EP11720485A EP2571364A1 (fr) | 2010-05-21 | 2011-05-19 | Agents herbicides pour cultures de riz tolérantes ou résistantes |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2571364A1 true EP2571364A1 (fr) | 2013-03-27 |
Family
ID=42931821
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP11720485A Withdrawn EP2571364A1 (fr) | 2010-05-21 | 2011-05-19 | Agents herbicides pour cultures de riz tolérantes ou résistantes |
Country Status (5)
Country | Link |
---|---|
US (1) | US20110287934A1 (fr) |
EP (1) | EP2571364A1 (fr) |
CN (1) | CN103025167A (fr) |
BR (1) | BR112012029634A2 (fr) |
WO (1) | WO2011144684A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021151753A1 (fr) | 2020-01-31 | 2021-08-05 | Basf Se | Associations d'herbicides comprenant du glufosinate et des inhibiteurs de ppo sélectionnés |
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US8859465B2 (en) * | 2011-11-30 | 2014-10-14 | Dow Agrosciences, Llc. | Synergistic herbicidal composition containing penoxsulam and glufosinate-ammonium |
JP2015500289A (ja) * | 2011-12-06 | 2015-01-05 | ダウ アグロサイエンシィズ エルエルシー | 特定のピリジンカルボン酸および(2,4−ジクロロフェノキシ)酢酸を含有する除草剤組成物 |
CN103299974A (zh) * | 2012-03-12 | 2013-09-18 | 雅马托农磁株式会社 | 插秧机搭载型液剂播洒装置、以及使用该装置的同时进行插秧与液剂播洒的方法 |
US8809232B2 (en) * | 2012-07-24 | 2014-08-19 | Dow Agroscience Llc | Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and halosulfuron, pyrazosulfuron and esprocarb |
US8895470B2 (en) * | 2012-07-24 | 2014-11-25 | Dow Agrosciences, Llc. | Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and glyphosate or glufosinate |
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BR122023021541A2 (pt) * | 2017-08-09 | 2024-01-09 | Basf Se | Mistura de herbicidas, composição pesticida e método de controle de vegetação |
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DE4107396A1 (de) | 1990-06-29 | 1992-01-02 | Bayer Ag | Stilbensynthase-gene aus weinrebe |
DE4029304A1 (de) | 1990-09-15 | 1992-03-19 | Hoechst Ag | Synergistische herbizide mittel |
SE467358B (sv) | 1990-12-21 | 1992-07-06 | Amylogene Hb | Genteknisk foeraendring av potatis foer bildning av staerkelse av amylopektintyp |
DE4104782B4 (de) | 1991-02-13 | 2006-05-11 | Bayer Cropscience Gmbh | Neue Plasmide, enthaltend DNA-Sequenzen, die Veränderungen der Karbohydratkonzentration und Karbohydratzusammensetzung in Pflanzen hervorrufen, sowie Pflanzen und Pflanzenzellen enthaltend dieses Plasmide |
PL212684B1 (pl) * | 1998-08-13 | 2012-11-30 | Bayer Cropscience Ag | Zastosowanie kompozycji herbicydów w uprawach kukurydzy i sposób zwalczania szkodliwych roslin w uprawach kukurydzy |
DE19836684A1 (de) * | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel für tolerante oder resistente Reiskulturen |
DE19836700A1 (de) * | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Herbizide Mittel für tolerante oder resistente Getreidekulturen |
CA2626103C (fr) | 2006-01-13 | 2013-07-30 | Dow Agrosciences Llc | 6-(poly-aryl substitute)-4-aminopicolinates et utilisations de ceux-ci comme herbicides |
EP1971579B1 (fr) | 2006-01-13 | 2010-07-28 | Dow AgroSciences LLC | Acides 2-(poly-substitue aryle)-6-amino-5-halo-4-pyrimidinecarboxylique et leur utilisation en tant qu herbicides |
KR20090024120A (ko) | 2006-04-10 | 2009-03-06 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 제초성 혼합물 |
BR122016022104B1 (pt) * | 2007-08-27 | 2019-03-19 | Dow Agrosciences Llc | Misturas herbicidas sinérgicas compreendendo certos ácidos carboxílicos de pirimidina ou piridina e certos herbicidas de cereal e arroz, composição herbicida, e métodos para controlar vegetação indesejável |
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2011
- 2011-05-19 EP EP11720485A patent/EP2571364A1/fr not_active Withdrawn
- 2011-05-19 WO PCT/EP2011/058107 patent/WO2011144684A1/fr active Application Filing
- 2011-05-19 US US13/111,494 patent/US20110287934A1/en not_active Abandoned
- 2011-05-19 BR BR112012029634A patent/BR112012029634A2/pt not_active IP Right Cessation
- 2011-05-19 CN CN2011800361894A patent/CN103025167A/zh active Pending
Non-Patent Citations (1)
Title |
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See references of WO2011144684A1 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021151753A1 (fr) | 2020-01-31 | 2021-08-05 | Basf Se | Associations d'herbicides comprenant du glufosinate et des inhibiteurs de ppo sélectionnés |
Also Published As
Publication number | Publication date |
---|---|
CN103025167A (zh) | 2013-04-03 |
WO2011144684A1 (fr) | 2011-11-24 |
US20110287934A1 (en) | 2011-11-24 |
BR112012029634A2 (pt) | 2015-10-20 |
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