CN1894220B - 除草的嘧啶 - Google Patents

除草的嘧啶 Download PDF

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Publication number: CN1894220B
Authority: CN; China
Prior art keywords: compound; alkyl; salt; amino; cyclopropyl
Prior art date: 2003-12-19
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.): Expired - Lifetime

Application number

CN200480037819XA

Other languages

English (en)

Chinese (zh)

Other versions

CN1894220A (zh

Inventor

D·A·克拉克

B·L·芬克尔斯坦

G·R·阿默尔

V·A·威藤巴赫

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kedihua Agricultural Technology Co ltd

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

2003-12-19

Filing date

2004-12-16

Publication date

2012-06-06

2004-12-16 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

2004-12-16 Priority claimed from PCT/US2004/042302 external-priority patent/WO2005063721A1/en

2007-01-10 Publication of CN1894220A publication Critical patent/CN1894220A/zh

2012-06-06 Application granted granted Critical

2012-06-06 Publication of CN1894220B publication Critical patent/CN1894220B/zh

2024-12-16 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 44
150000003230 pyrimidines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 1103
150000003839 salts Chemical class 0.000 claims abstract description 455
239000000203 mixture Substances 0.000 claims abstract description 114
229910052736 halogen Inorganic materials 0.000 claims abstract description 68
150000002367 halogens Chemical class 0.000 claims abstract description 68
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 54
238000000034 method Methods 0.000 claims abstract description 50
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 44
239000004009 herbicide Substances 0.000 claims abstract description 35
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 27
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
229910052740 iodine Inorganic materials 0.000 claims abstract description 16
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
-1 C1-C6Alkyl Chemical group 0.000 claims description 164
AAVNVYQKXOAXAR-UHFFFAOYSA-N 5-chloro-2-cyclopropylpyrimidine-4-carboxylic acid Chemical class C1=C(Cl)C(C(=O)O)=NC(C2CC2)=N1 AAVNVYQKXOAXAR-UHFFFAOYSA-N 0.000 claims description 152
ZENKESXKWBIZCV-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-1,3-benzodioxin-6-amine Chemical group O1C(F)(F)OC(F)(F)C2=CC(N)=CC=C21 ZENKESXKWBIZCV-UHFFFAOYSA-N 0.000 claims description 65
239000007787 solid Substances 0.000 claims description 41
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
239000005864 Sulphur Substances 0.000 claims description 36
239000005584 Metsulfuron-methyl Substances 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 34
125000004414 alkyl thio group Chemical group 0.000 claims description 32
229910052799 carbon Inorganic materials 0.000 claims description 29
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
125000003368 amide group Chemical group 0.000 claims description 25
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 claims description 24
239000003085 diluting agent Substances 0.000 claims description 22
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
239000004094 surface-active agent Substances 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
239000005586 Nicosulfuron Substances 0.000 claims description 19
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 19
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 19
IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 claims description 18
239000005469 Azimsulfuron Substances 0.000 claims description 18
HYJODZUSLXOFNC-UHFFFAOYSA-N [S].[Cl] Chemical compound [S].[Cl] HYJODZUSLXOFNC-UHFFFAOYSA-N 0.000 claims description 18
MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 claims description 18
230000015572 biosynthetic process Effects 0.000 claims description 18
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 17
239000000460 chlorine Substances 0.000 claims description 16
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 claims description 15
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 claims description 15
239000003666 Amidosulfuron Substances 0.000 claims description 15
CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims description 15
239000005472 Bensulfuron methyl Substances 0.000 claims description 15
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 15
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 15
239000005529 Florasulam Substances 0.000 claims description 15
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 15
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 claims description 15
239000005560 Foramsulfuron Substances 0.000 claims description 15
239000005564 Halosulfuron methyl Substances 0.000 claims description 15
FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 claims description 15
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 15
239000005567 Imazosulfuron Substances 0.000 claims description 15
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 15
239000005582 Metosulam Substances 0.000 claims description 15
VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 claims description 15
RRKHIAYNPVQKEF-UHFFFAOYSA-N Pyriftalid Chemical compound COC1=CC(OC)=NC(SC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 RRKHIAYNPVQKEF-UHFFFAOYSA-N 0.000 claims description 15
239000005616 Rimsulfuron Substances 0.000 claims description 15
239000005619 Sulfosulfuron Substances 0.000 claims description 15
239000005623 Thifensulfuron-methyl Substances 0.000 claims description 15
239000005629 Tritosulfuron Substances 0.000 claims description 15
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 15
NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 15
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 claims description 15
239000011630 iodine Substances 0.000 claims description 15
ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 claims description 15
AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 claims description 15
USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 claims description 15
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 15
JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical class [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 claims description 15
ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 claims description 15
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 15
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 claims description 15
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 claims description 15
KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 claims description 15
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 14
239000005566 Imazamox Substances 0.000 claims description 14
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 14
IRLGCAJYYKDTCG-UHFFFAOYSA-N ethametsulfuron Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 IRLGCAJYYKDTCG-UHFFFAOYSA-N 0.000 claims description 14
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 claims description 14
BAOWVDHYZBLYMB-UHFFFAOYSA-N [F].C1=CC=NC=C1 Chemical compound [F].C1=CC=NC=C1 BAOWVDHYZBLYMB-UHFFFAOYSA-N 0.000 claims description 13
125000000304 alkynyl group Chemical group 0.000 claims description 13
125000004429 atom Chemical group 0.000 claims description 12
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 11
229930192334 Auxin Natural products 0.000 claims description 11
239000002363 auxin Substances 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 11
239000007788 liquid Substances 0.000 claims description 10
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 9
230000000994 depressogenic effect Effects 0.000 claims description 9
229940079593 drug Drugs 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
230000008635 plant growth Effects 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
QTJUOHMUTZFYDB-UHFFFAOYSA-N CCOC(C1=NC(C2CC2)=NC=C1Cl)=O Chemical class CCOC(C1=NC(C2CC2)=NC=C1Cl)=O QTJUOHMUTZFYDB-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
UNTJFTYLMTYCGQ-UHFFFAOYSA-N methyl 5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical class C1=C(Br)C(C(=O)OC)=NC(C2CC2)=N1 UNTJFTYLMTYCGQ-UHFFFAOYSA-N 0.000 claims description 6
GFVYDJYJZMMZQS-UHFFFAOYSA-N methyl 5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical class C1=C(Cl)C(C(=O)OC)=NC(C2CC2)=N1 GFVYDJYJZMMZQS-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 claims description 5
CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 5
IKDLJHIRCTZDND-UHFFFAOYSA-N 2-cyclopropyl-4-oxo-1h-pyrimidine-6-carboxylic acid Chemical group OC(=O)C1=CC(=O)NC(C2CC2)=N1 IKDLJHIRCTZDND-UHFFFAOYSA-N 0.000 claims description 5
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 claims description 5
DXXUDDJXKCDFRZ-UHFFFAOYSA-N CCOC(=O)C1=NC(=NC=C1Br)C2CC2 Chemical class CCOC(=O)C1=NC(=NC=C1Br)C2CC2 DXXUDDJXKCDFRZ-UHFFFAOYSA-N 0.000 claims description 5
QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 claims description 5
239000005514 Flazasulfuron Substances 0.000 claims description 5
HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 claims description 5
239000005981 Imazaquin Substances 0.000 claims description 5
239000005589 Oxasulfuron Substances 0.000 claims description 5
239000005604 Prosulfuron Substances 0.000 claims description 5
LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims description 5
CNILNQMBAHKMFS-UHFFFAOYSA-M Pyrithiobac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C([O-])=O)=N1 CNILNQMBAHKMFS-UHFFFAOYSA-M 0.000 claims description 5
150000003863 ammonium salts Chemical class 0.000 claims description 5
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 5
UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 claims description 5
JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 claims description 5
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 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
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 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 claims description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
230000002708 enhancing effect Effects 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
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JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
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150000004965 peroxy acids Chemical class 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000007793 ph indicator Substances 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
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LIOPHZNMBKHGAV-UHFFFAOYSA-M potassium;2-(phosphonomethylamino)acetate Chemical compound [K+].OC(=O)CNCP(O)([O-])=O LIOPHZNMBKHGAV-UHFFFAOYSA-M 0.000 description 1
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AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
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IKVXBIIHQGXQRQ-UHFFFAOYSA-N propan-2-yl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC(C)C)C(=O)C1=CC=CC=C1 IKVXBIIHQGXQRQ-UHFFFAOYSA-N 0.000 description 1
FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
235000012950 rattan cane Nutrition 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 1
AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical class [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
239000002383 tung oil Substances 0.000 description 1
230000004222 uncontrolled growth Effects 0.000 description 1
244000045561 useful plants Species 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

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Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CN200480037819XA 2003-12-19 2004-12-16 除草的嘧啶 Expired - Lifetime CN1894220B (zh)

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US53130003P	2003-12-19	2003-12-19
US60/531,300		2003-12-19
US59839704P	2004-08-03	2004-08-03
US60/598,397		2004-08-03
PCT/US2004/042302 WO2005063721A1 (en)	2003-12-19	2004-12-16	Herbicidal pyrimidines

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GT (1)	GT200400272A (ru)
TN (1)	TNSN06184A1 (ru)
UA (1)	UA84724C2 (ru)
ZA (1)	ZA200604258B (ru)

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PL2514313T3 (pl) *	2007-08-27	2015-07-31	Dow Agrosciences Llc	Synergistyczna kompozycja chwastobójcza zawierająca pewne kwasy pirydynokarboksylowe oraz pewne herbicydy stosowane w uprawie zbóż i ryżu
CN101784531B (zh) *	2007-08-30	2013-05-01	陶氏益农公司	2-(取代的苯基)-6-氨基-5-烷氧基、硫代烷氧基和氨基烷基嘧啶-4-羧酸衍生物及其作为除草剂的用途
CN102066336B (zh) *	2008-04-18	2014-02-19	陶氏益农公司	2-(取代的苯基)-6-羟基或烷氧基-5-取代的-嘧啶-4-羧酸酯和它们作为除草剂的用途
MX2011001553A (es) *	2008-08-12	2011-03-29	Du Pont	Metodo para controlar vegetacion mimosoideae no deseada.
EP2191716A1 (de) *	2008-11-29	2010-06-02	Bayer CropScience AG	Herbizid-Safener-Kombination
EP2229813A1 (de) *	2009-03-21	2010-09-22	Bayer CropScience AG	Pyrimidin-4-ylpropandinitril-derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
TWI596088B (zh) *	2011-01-25	2017-08-21	陶氏農業科學公司	４－胺基－６－（經取代的苯基）吡啶甲酸酯及６－胺基－２－（經取代的苯基）－４－嘧啶羧酸酯之芳烷酯以及其等作為除草劑之用途
MX367606B (es) *	2012-09-04	2019-08-28	Dow Agrosciences Llc Star	Control sinérgico de malezas a partir de aplicaciones de aminociclopiraclor y clopiralid.
CN110583666A (zh) *	2012-09-28	2019-12-20	美国陶氏益农公司	来自施用环丙嘧啶酸和氯氟吡氧乙酸的协同杂草控制
US9113629B2 (en) *	2013-03-15	2015-08-25	Dow Agrosciences Llc	4-amino-6-(4-substituted-phenyl)-picolinates and 6-amino-2-(4-substituted-phenyl)-pyrimidine-4-carboxylates and their use as herbicides
EA038960B1 (ru) *	2015-01-30	2021-11-15	Басф Се	Гербицидные фенилпиримидины
CN106187911A (zh) *	2016-07-04	2016-12-07	烟台凯博医药科技有限公司	2‑三氟甲基嘧啶‑4‑羧酸及其衍生物和制备方法
US11180470B2 (en) *	2016-07-25	2021-11-23	Basf Se	Herbicidal pyrimidine compounds
EP3490985B1 (en) *	2016-07-26	2020-08-05	Basf Se	Herbicidal pyrimidine compounds
CN108774179B (zh) *	2018-05-29	2020-01-21	青岛清原化合物有限公司	一种取代的嘧啶-4-甲酸衍生物及其除草组合物和用途
CN108586357B (zh) *	2018-07-05	2020-01-21	青岛清原化合物有限公司	取代的嘧啶甲酰基肟衍生物及其制备方法、除草组合物和应用
WO2020133403A1 (zh) *	2018-12-29	2020-07-02	青岛清原化合物有限公司	取代的嘧啶芳酯衍生物及其制备方法、除草组合物和应用
US20220289708A1 (en) *	2019-07-22	2022-09-15	Bayer Aktiengesellschaft	Substituted n-phenyl uracils, salts thereof and their use as herbicidal agents

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- 2004-12-16 CN CN200480037819XA patent/CN1894220B/zh not_active Expired - Lifetime
- 2004-12-16 ZA ZA200604258A patent/ZA200604258B/en unknown
- 2004-12-17 GT GT200400272A patent/GT200400272A/es unknown
2006
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GT200400272A (es)	2005-09-09
UA84724C2 (ru)	2008-11-25
CN1894220A (zh)	2007-01-10
TNSN06184A1 (en)	2007-11-15
ZA200604258B (en)	2008-07-30

Publication	Publication Date	Title
CN102675218B (zh)	2015-04-01	除草的嘧啶
CN1894220B (zh)	2012-06-06	除草的嘧啶
US20100298141A1 (en)	2010-11-25	Substituted pyridine n-oxide herbicides
TWI709554B (zh)	2020-11-11	吡咯啶酮除草劑
TWI732289B (zh)	2021-07-01	嗒𠯤酮除草劑
TWI713530B (zh)	2020-12-21	作為除草劑之嘧啶氧基苯衍生物
CN101945856A (zh)	2011-01-12	除草剂哒嗪酮衍生物
AU2018239940A1 (en)	2019-10-03	Herbicidal mixture, composition and method
EP3601263B1 (en)	2021-10-13	Novel pyridazinone herbicides
CN108884055A (zh)	2018-11-23	哒嗪酮系化合物或其盐、以及含有它们的除草剂
TW201625554A (zh)	2016-07-16	作為除草劑之雙芳基兒茶酚衍生物
WO2006062979A1 (en)	2006-06-15	Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives
US20060069132A1 (en)	2006-03-30	Azolecarboxamide herbicides
US7138361B2 (en)	2006-11-21	Herbicidal heterocycles
WO1998056789A1 (en)	1998-12-17	Pyrimidinyl azole herbicides
US20130005568A1 (en)	2013-01-03	Safened herbicidal mixtures
US20130303369A1 (en)	2013-11-14	Fatty Amine Salts Of Herbicidal Pyrimidines
AU2011203576B2 (en)	2013-01-31	Herbicidal Pyrimidines

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