NZ547251A - Herbicidal pyrimidines - Google Patents
Herbicidal pyrimidinesInfo
- Publication number
- NZ547251A NZ547251A NZ547251A NZ54725104A NZ547251A NZ 547251 A NZ547251 A NZ 547251A NZ 547251 A NZ547251 A NZ 547251A NZ 54725104 A NZ54725104 A NZ 54725104A NZ 547251 A NZ547251 A NZ 547251A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methyl
- amino
- alkyl
- compound
- chloro
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 43
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 215
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 60
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 239000004009 herbicide Substances 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 138
- 229910052736 halogen Inorganic materials 0.000 claims description 75
- 150000002367 halogens Chemical group 0.000 claims description 74
- 125000001188 haloalkyl group Chemical group 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 59
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- -1 cyano, hydroxycarbonyl Chemical group 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 31
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 30
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 27
- 125000003282 alkyl amino group Chemical group 0.000 claims description 26
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 20
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 239000007787 solid Substances 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 241000196324 Embryophyta Species 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
- 230000012010 growth Effects 0.000 claims description 7
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl 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
- 229940125904 compound 1 Drugs 0.000 claims description 6
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- PXCZEJRHVNHLHI-UHFFFAOYSA-N ethyl 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C=2C=CC(Cl)=CC=2)=N1 PXCZEJRHVNHLHI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- BTUSKWROSWXMPG-UHFFFAOYSA-N 6-amino-2-(4-bromophenyl)-5-chloropyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C=2C=CC(Br)=CC=2)=N1 BTUSKWROSWXMPG-UHFFFAOYSA-N 0.000 claims description 4
- IFNGRCNEIXJJOA-UHFFFAOYSA-N 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C=2C=CC(Cl)=CC=2)=N1 IFNGRCNEIXJJOA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- ASZOFVYKIHWIRJ-UHFFFAOYSA-N ethyl 6-amino-2-(4-bromophenyl)-5-chloropyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C=2C=CC(Br)=CC=2)=N1 ASZOFVYKIHWIRJ-UHFFFAOYSA-N 0.000 claims description 4
- DFNPYOBOAGIMIV-UHFFFAOYSA-N ethyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Br)C(C(=O)OCC)=NC(C2CC2)=N1 DFNPYOBOAGIMIV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 4
- NRMIASFSJMZYBG-UHFFFAOYSA-N methyl 6-amino-5-chloro-2-(4-chlorophenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C=CC(Cl)=CC=2)=N1 NRMIASFSJMZYBG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 3
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims description 3
- 125000005134 alkynylsulfinyl group Chemical group 0.000 claims description 3
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 3
- 125000005109 alkynylthio group Chemical group 0.000 claims description 3
- MDWRNPOBHVLALB-UHFFFAOYSA-N aminocyclopyrachlor-methyl Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C2CC2)=N1 MDWRNPOBHVLALB-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- GKGQGHXICXHRDC-UHFFFAOYSA-N benzyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound BrC=1C(N)=NC(C2CC2)=NC=1C(=O)OCC1=CC=CC=C1 GKGQGHXICXHRDC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 3
- NMPOJZJYKCNZDZ-UHFFFAOYSA-N ethyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OCC)=NC(C2CC2)=N1 NMPOJZJYKCNZDZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- RDTDHIKLTPWILZ-UHFFFAOYSA-N methyl 6-amino-2-(4-bromophenyl)-5-chloropyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C=CC(Br)=CC=2)=N1 RDTDHIKLTPWILZ-UHFFFAOYSA-N 0.000 claims description 3
- YDLGIPUCLCBOMQ-UHFFFAOYSA-N methyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate Chemical compound NC1=C(Br)C(C(=O)OC)=NC(C2CC2)=N1 YDLGIPUCLCBOMQ-UHFFFAOYSA-N 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- PLSRLZJGTQNHJW-UHFFFAOYSA-N benzyl 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound ClC=1C(N)=NC(C2CC2)=NC=1C(=O)OCC1=CC=CC=C1 PLSRLZJGTQNHJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 2
- CYILDCWNUWUWEG-UHFFFAOYSA-M sodium;6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate Chemical compound [Na+].[O-]C(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 CYILDCWNUWUWEG-UHFFFAOYSA-M 0.000 claims description 2
- 239000005584 Metsulfuron-methyl Substances 0.000 claims 30
- 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 30
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims 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 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 15
- 239000005586 Nicosulfuron Substances 0.000 claims 14
- 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 14
- 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 12
- 239000005496 Chlorsulfuron Substances 0.000 claims 12
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims 12
- 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 12
- 239000005472 Bensulfuron methyl Substances 0.000 claims 6
- 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 6
- 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 6
- 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 6
- 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 6
- 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 6
- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 claims 6
- 230000000996 additive effect Effects 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 238000011282 treatment Methods 0.000 claims 5
- 229930192334 Auxin Natural products 0.000 claims 4
- 239000002363 auxin Substances 0.000 claims 4
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 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 3
- DAGDLSRRQJATCV-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1OCCBr DAGDLSRRQJATCV-UHFFFAOYSA-N 0.000 claims 3
- 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 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 3
- 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 3
- QEGVVEOAVNHRAA-UHFFFAOYSA-N 2-chloro-6-(4,6-dimethoxypyrimidin-2-yl)sulfanylbenzoic acid Chemical compound COC1=CC(OC)=NC(SC=2C(=C(Cl)C=CC=2)C(O)=O)=N1 QEGVVEOAVNHRAA-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 239000003666 Amidosulfuron Substances 0.000 claims 3
- 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 3
- 239000005469 Azimsulfuron Substances 0.000 claims 3
- 239000005488 Bispyribac Substances 0.000 claims 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 3
- 240000001579 Cirsium arvense Species 0.000 claims 3
- 235000005918 Cirsium arvense Nutrition 0.000 claims 3
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- 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 3
- 239000005514 Flazasulfuron Substances 0.000 claims 3
- 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 3
- 239000005529 Florasulam Substances 0.000 claims 3
- 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 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 3
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 claims 3
- 239000005560 Foramsulfuron Substances 0.000 claims 3
- 239000005564 Halosulfuron methyl Substances 0.000 claims 3
- 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 3
- 239000005566 Imazamox Substances 0.000 claims 3
- 239000005981 Imazaquin Substances 0.000 claims 3
- 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 3
- 239000005582 Metosulam Substances 0.000 claims 3
- 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 3
- 239000005592 Penoxsulam Substances 0.000 claims 3
- 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 3
- 239000005601 Propoxycarbazone Substances 0.000 claims 3
- 239000005604 Prosulfuron Substances 0.000 claims 3
- 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 3
- 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 3
- 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 3
- 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 3
- 239000005619 Sulfosulfuron Substances 0.000 claims 3
- 239000005629 Tritosulfuron Substances 0.000 claims 3
- KWAIHLIXESXTJL-UHFFFAOYSA-N aminocyclopyrachlor Chemical compound OC(=O)C1=C(Cl)C(N)=NC(C2CC2)=N1 KWAIHLIXESXTJL-UHFFFAOYSA-N 0.000 claims 3
- 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 3
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- MGDQXDDFHRHNEV-UHFFFAOYSA-N 5,6-dichloro-2-cyclopropylpyrimidine-4-carboxylic acid phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O.ClC1=C(Cl)C(C(=O)O)=NC(C2CC2)=N1 MGDQXDDFHRHNEV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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- 229930194542 Keto Natural products 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
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- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
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- 235000021536 Sugar beet Nutrition 0.000 description 1
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
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- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 229950010286 diolamine Drugs 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
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- 238000005886 esterification reaction Methods 0.000 description 1
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
- HYVRRAANXHHPGH-UHFFFAOYSA-N ethyl 4,4-diethoxy-3-oxobutanoate Chemical compound CCOC(OCC)C(=O)CC(=O)OCC HYVRRAANXHHPGH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 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 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 108091028606 miR-1 stem-loop Proteins 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
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- 150000004291 polyenes Chemical class 0.000 description 1
- 238000000746 purification Methods 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
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 229960001922 sodium perborate Drugs 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53130003P | 2003-12-19 | 2003-12-19 | |
| US59839704P | 2004-08-03 | 2004-08-03 | |
| PCT/US2004/042302 WO2005063721A1 (en) | 2003-12-19 | 2004-12-16 | Herbicidal pyrimidines |
Publications (1)
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| NZ547251A true NZ547251A (en) | 2009-09-25 |
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| Application Number | Title | Priority Date | Filing Date |
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| NZ547251A NZ547251A (en) | 2003-12-19 | 2004-12-16 | Herbicidal pyrimidines |
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| TWI355894B (en) * | 2003-12-19 | 2012-01-11 | Du Pont | Herbicidal pyrimidines |
| WO2006062979A1 (en) * | 2004-12-06 | 2006-06-15 | E.I. Dupont De Nemours And Company | Herbicidal 6-cyclopropyl-substitute 4-aminopicolinic acid derivatives |
| IN2014DN02255A (enExample) | 2005-02-11 | 2015-07-10 | Dow Agrosciences Llc | |
| PL1877384T3 (pl) * | 2005-05-06 | 2011-09-30 | Du Pont | Sposób wytwarzania opcjonalnie 2-podstawionych kwasów 1,6-dihydro-6-okso-4-pirymidynokarboksylowych |
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