BR112020003047A2 - compostos herbicidas - Google Patents

Info

Publication number

BR112020003047A2

BR112020003047A2 BR112020003047-3A BR112020003047A BR112020003047A2 BR 112020003047 A2 BR112020003047 A2 BR 112020003047A2 BR 112020003047 A BR112020003047 A BR 112020003047A BR 112020003047 A2 BR112020003047 A2 BR 112020003047A2

Authority

BR

Brazil

Prior art keywords

formula

group

compound

c6alkyl

pyridazin

Prior art date

2017-08-17

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 338
• 230000002363 herbicidal effect Effects 0.000 title claims description 17
• 239000000203 mixture Substances 0.000 claims description 179
• 239000001257 hydrogen Substances 0.000 claims description 109
• 229910052739 hydrogen Inorganic materials 0.000 claims description 109
• -1 C1- C6alkyl Chemical group 0.000 claims description 89
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 86
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
• 125000001424 substituent group Chemical group 0.000 claims description 62
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
• 229910052736 halogen Inorganic materials 0.000 claims description 43
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 150000002431 hydrogen Chemical class 0.000 claims description 38
• 125000005842 heteroatom Chemical group 0.000 claims description 37
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 36
• 238000000034 method Methods 0.000 claims description 35
• 239000000126 substance Substances 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 31
• DBNKMEZCQQZZBD-UHFFFAOYSA-N 2-pyridazin-4-ylpyrimidine Chemical compound N1=CC=CN=C1C1=CC=NN=C1 DBNKMEZCQQZZBD-UHFFFAOYSA-N 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 239000002168 alkylating agent Substances 0.000 claims description 9
• 229940100198 alkylating agent Drugs 0.000 claims description 9
• 239000000460 chlorine Substances 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 8
• PKILSTFBXYVVTA-UHFFFAOYSA-N 3-pyridazin-4-ylpyridazine Chemical compound C1=CN=NC(C=2C=NN=CC=2)=C1 PKILSTFBXYVVTA-UHFFFAOYSA-N 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 239000003054 catalyst Substances 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000002577 pseudohalo group Chemical group 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
• WVIMSFDSAWGNPE-UHFFFAOYSA-N 2-pyridazin-4-ylpyrazine Chemical compound C1=NC=CN=C1C1=CC=NN=C1 WVIMSFDSAWGNPE-UHFFFAOYSA-N 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• 229910000080 stannane Inorganic materials 0.000 claims description 7
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
• XXTYHAFSJIWNJN-UHFFFAOYSA-N 4-pyridazin-4-ylpyrimidine Chemical compound N1=CN=C(C=C1)C1=CN=NC=C1 XXTYHAFSJIWNJN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 150000003536 tetrazoles Chemical class 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 239000012442 inert solvent Substances 0.000 claims description 4
• 229910052763 palladium Inorganic materials 0.000 claims description 4
• 239000003905 agrochemical Substances 0.000 claims description 3
• 230000008635 plant growth Effects 0.000 claims description 3
• RFFQGKVABDVQQE-UHFFFAOYSA-N 4-pyridazin-4-ylpyridazine Chemical compound N1=NC=CC(C=2C=NN=CC=2)=C1 RFFQGKVABDVQQE-UHFFFAOYSA-N 0.000 claims description 2
• 239000012872 agrochemical composition Substances 0.000 claims description 2
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• 239000000575 pesticide Substances 0.000 abstract description 7
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 165
• 238000002360 preparation method Methods 0.000 description 146
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
• 239000011541 reaction mixture Substances 0.000 description 118
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• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 82
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 78
• 239000007787 solid Substances 0.000 description 72
• 239000000243 solution Substances 0.000 description 72
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 70
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
• 238000006243 chemical reaction Methods 0.000 description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
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• 235000019439 ethyl acetate Nutrition 0.000 description 59
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 48
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 47
• 241000196324 Embryophyta Species 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• 239000004480 active ingredient Substances 0.000 description 33
• 239000000377 silicon dioxide Substances 0.000 description 33
• 238000004007 reversed phase HPLC Methods 0.000 description 30
• 239000002904 solvent Substances 0.000 description 30
• 239000012044 organic layer Substances 0.000 description 28
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
• 244000058871 Echinochloa crus-galli Species 0.000 description 25
• 240000007218 Ipomoea hederacea Species 0.000 description 25
• 240000004296 Lolium perenne Species 0.000 description 25
• 235000011999 Panicum crusgalli Nutrition 0.000 description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
• 235000014716 Eleusine indica Nutrition 0.000 description 24
• 244000025670 Eleusine indica Species 0.000 description 24
• 239000012299 nitrogen atmosphere Substances 0.000 description 23
• 244000152970 Digitaria sanguinalis Species 0.000 description 22
• 235000010823 Digitaria sanguinalis Nutrition 0.000 description 22
• 244000048459 Euphorbia cyathophora Species 0.000 description 22
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
• 235000017016 Setaria faberi Nutrition 0.000 description 21
• 241001355178 Setaria faberi Species 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 238000009472 formulation Methods 0.000 description 21
• 125000005843 halogen group Chemical group 0.000 description 21
• 241001542006 Amaranthus palmeri Species 0.000 description 20
• 240000006122 Chenopodium album Species 0.000 description 20
• 235000009344 Chenopodium album Nutrition 0.000 description 20
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
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• 239000003480 eluent Substances 0.000 description 20
• 239000007788 liquid Substances 0.000 description 20
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• 229910052938 sodium sulfate Inorganic materials 0.000 description 18
• 235000011152 sodium sulphate Nutrition 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• 150000003254 radicals Chemical class 0.000 description 17
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• 239000010410 layer Substances 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 15
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
• 238000010828 elution Methods 0.000 description 14
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 11
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 11
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
• 235000019341 magnesium sulphate Nutrition 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 239000004094 surface-active agent Substances 0.000 description 10
• 239000003981 vehicle Substances 0.000 description 10
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
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• 239000000047 product Substances 0.000 description 9
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• UDLLSOQWYYRFPP-UHFFFAOYSA-N tributyl(pyridazin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NN=C1 UDLLSOQWYYRFPP-UHFFFAOYSA-N 0.000 description 9
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