EA037101B1 - Производные 2-(фенилокси- или фенилтио)пиримидина в качестве гербицидов - Google Patents

Info

Publication number

EA037101B1

EA037101B1 EA201792433A EA201792433A EA037101B1 EA 037101 B1 EA037101 B1 EA 037101B1 EA 201792433 A EA201792433 A EA 201792433A EA 201792433 A EA201792433 A EA 201792433A EA 037101 B1 EA037101 B1 EA 037101B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

compound

chloro

haloalkyl

methyl

Prior art date

2015-06-05

Links

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• 239000004009 herbicide Substances 0.000 title claims description 44
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 438
• 239000000203 mixture Substances 0.000 claims abstract description 105
• 238000000034 method Methods 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 31
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 16
• -1 C1-C 6 -nitroalkyl Chemical group 0.000 claims description 294
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 125
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 116
• 229910052736 halogen Inorganic materials 0.000 claims description 65
• 150000002367 halogens Chemical group 0.000 claims description 64
• 230000002363 herbicidal effect Effects 0.000 claims description 43
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 34
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
• 239000004480 active ingredient Substances 0.000 claims description 29
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 27
• 239000003085 diluting agent Substances 0.000 claims description 27
• 239000007788 liquid Substances 0.000 claims description 25
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• 239000007787 solid Substances 0.000 claims description 22
• 239000004094 surface-active agent Substances 0.000 claims description 22
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
• 230000012010 growth Effects 0.000 claims description 14
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 12
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
• 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 239000005562 Glyphosate Substances 0.000 claims description 10
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 10
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 9
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 8
• 229940097068 glyphosate Drugs 0.000 claims description 8
• 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 claims description 7
• UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 7
• 239000005489 Bromoxynil Substances 0.000 claims description 7
• 239000005504 Dicamba Substances 0.000 claims description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
• IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 7
• 239000005476 Bentazone Substances 0.000 claims description 6
• 239000005561 Glufosinate Substances 0.000 claims description 6
• MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 6
• 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 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
• JXTZGADMSRDNKF-UHFFFAOYSA-N 1-[2-chloro-6-(5-chloropyrimidin-2-yl)oxyphenyl]-4,4,4-trifluorobutan-1-one Chemical compound FC(F)(F)CCC(=O)C1=C(Cl)C=CC=C1OC1=NC=C(Cl)C=N1 JXTZGADMSRDNKF-UHFFFAOYSA-N 0.000 claims description 5
• VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 5
• 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 5
• 239000005529 Florasulam Substances 0.000 claims description 5
• QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 5
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
• 239000005578 Mesotrione Substances 0.000 claims description 5
• 239000005616 Rimsulfuron Substances 0.000 claims description 5
• XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 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 claims description 4
• 239000005531 Flufenacet Substances 0.000 claims description 4
• 239000005532 Flumioxazine Substances 0.000 claims description 4
• 239000005620 Tembotrione Substances 0.000 claims description 4
• 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 4
• BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• QBSOCTPGWBPYNI-UHFFFAOYSA-N 1-[2-(5-bromopyrimidin-2-yl)oxyphenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OC1=NC=C(Br)C=N1 QBSOCTPGWBPYNI-UHFFFAOYSA-N 0.000 claims description 2
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
• 239000005626 Tribenuron Substances 0.000 claims 2
• OLZQTUCTGLHFTQ-UHFFFAOYSA-N octan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical group CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl OLZQTUCTGLHFTQ-UHFFFAOYSA-N 0.000 claims 2
• 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 claims 2
• 230000008520 organization Effects 0.000 claims 1
• 125000000565 sulfonamide group Chemical group 0.000 claims 1
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 100
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• 241000196324 Embryophyta Species 0.000 description 83
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
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• OJASMMNWWIJWFK-KUSCCAPHSA-N (3r)-1-[[4-[[(3r)-3-(diethylcarbamoyl)piperidin-1-yl]methyl]phenyl]methyl]-n,n-diethylpiperidine-3-carboxamide;dihydrobromide Chemical compound Br.Br.C1[C@H](C(=O)N(CC)CC)CCCN1CC(C=C1)=CC=C1CN1C[C@H](C(=O)N(CC)CC)CCC1 OJASMMNWWIJWFK-KUSCCAPHSA-N 0.000 description 50
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