BR112018068206B1 - Composto, composição compreendendo o mesmo e método de combate, prevenção ou controle de doenças fitopatogênicas - Google Patents

Info

Publication number

BR112018068206B1

BR112018068206B1 BR112018068206-3A BR112018068206A BR112018068206B1 BR 112018068206 B1 BR112018068206 B1 BR 112018068206B1 BR 112018068206 A BR112018068206 A BR 112018068206A BR 112018068206 B1 BR112018068206 B1 BR 112018068206B1

Authority

BR

Brazil

Prior art keywords

methyl

fluorine

hydrogen

alkyl

independently selected

Prior art date

2016-03-10

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 262
• 239000000203 mixture Substances 0.000 title claims abstract description 109
• 238000000034 method Methods 0.000 title claims description 32
• 201000010099 disease Diseases 0.000 title claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 18
• 230000002265 prevention Effects 0.000 title description 2
• 239000000463 material Substances 0.000 claims abstract description 25
• 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 17
• 229910052731 fluorine Inorganic materials 0.000 claims description 126
• 239000011737 fluorine Substances 0.000 claims description 126
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
• 239000001257 hydrogen Substances 0.000 claims description 120
• 229910052739 hydrogen Inorganic materials 0.000 claims description 120
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 118
• -1 cyano, formyl Chemical group 0.000 claims description 87
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 67
• 125000001424 substituent group Chemical group 0.000 claims description 67
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 57
• 239000000460 chlorine Substances 0.000 claims description 57
• 229910052801 chlorine Inorganic materials 0.000 claims description 57
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 46
• 150000003839 salts Chemical class 0.000 claims description 46
• 239000004480 active ingredient Substances 0.000 claims description 43
• 150000001204 N-oxides Chemical class 0.000 claims description 41
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 40
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
• 229910052736 halogen Inorganic materials 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• 150000002367 halogens Chemical group 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000004414 alkyl thio group Chemical group 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 19
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 17
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
• 230000000855 fungicidal effect Effects 0.000 claims description 15
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 10
• 125000005336 allyloxy group Chemical group 0.000 claims description 10
• 239000000417 fungicide Substances 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 4
• SPDIXQXJBZYVFU-UHFFFAOYSA-N 7,8-difluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(F)(F)F)(C)NC(=O)C=1C=NC2=C(C(=CC=C2C=1)F)F SPDIXQXJBZYVFU-UHFFFAOYSA-N 0.000 claims description 4
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• SGSTZURMXPJQSD-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpent-4-en-2-yl)-8-fluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(=C)C)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F SGSTZURMXPJQSD-UHFFFAOYSA-N 0.000 claims description 3
• VMSKKUQFMJAMHW-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpentan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)C)(C)NC(=O)C=1C=NC2=CC=CC=C2C=1 VMSKKUQFMJAMHW-UHFFFAOYSA-N 0.000 claims description 3
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• RBGBKPQEQDWVNS-UHFFFAOYSA-N 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(F)(F)F)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F RBGBKPQEQDWVNS-UHFFFAOYSA-N 0.000 claims description 2
• MPXHQDZAKMYKDH-UHFFFAOYSA-N 8-fluoro-N-(4-fluoro-2,4-dimethyl-1-phenylpentan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)(C)F)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F MPXHQDZAKMYKDH-UHFFFAOYSA-N 0.000 claims description 2
• RQQOBSVFTXVGRY-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)C)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F RQQOBSVFTXVGRY-UHFFFAOYSA-N 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 239000004149 tartrazine Substances 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 27
• DELYUKIVFXSHRY-UHFFFAOYSA-N 8-chloro-N-(2,4-dimethyl-1-phenylpentan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)C)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)Cl DELYUKIVFXSHRY-UHFFFAOYSA-N 0.000 claims 1
• SNIWVOJHWAMHEX-UHFFFAOYSA-N 8-chloro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(F)(F)F)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)Cl SNIWVOJHWAMHEX-UHFFFAOYSA-N 0.000 claims 1
• VQEZYYYRCVORSG-UHFFFAOYSA-N 8-fluoro-N-(2,4,4-trimethyl-1-phenylpentan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)(C)C)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F VQEZYYYRCVORSG-UHFFFAOYSA-N 0.000 claims 1
• DTOZPNHGPWULBM-UHFFFAOYSA-N 8-fluoro-N-[1-(3-fluorophenyl)-2,4-dimethylpentan-2-yl]quinoline-3-carboxamide Chemical compound FC=1C=CC=C2C=C(C=NC=12)C(=O)NC(CC(C)C)(C)CC1=CC(=CC=C1)F DTOZPNHGPWULBM-UHFFFAOYSA-N 0.000 claims 1
• MFCWAISHNJBJRT-UHFFFAOYSA-N 8-fluoro-N-[2-methyl-1-(1-methylcyclopropyl)-3-phenylpropan-2-yl]quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC1(CC1)C)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)F MFCWAISHNJBJRT-UHFFFAOYSA-N 0.000 claims 1
• MFMHMZLCEKDCQV-UHFFFAOYSA-N 8-fluoro-N-[4,4,4-trifluoro-1-(3-fluorophenyl)-2-methylbutan-2-yl]quinoline-3-carboxamide Chemical compound FC=1C=CC=C2C=C(C=NC=12)C(=O)NC(CC(F)(F)F)(C)CC1=CC(=CC=C1)F MFMHMZLCEKDCQV-UHFFFAOYSA-N 0.000 claims 1
• RLXNCCMFGMORFD-UHFFFAOYSA-N 8-methyl-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(F)(F)F)(C)NC(=O)C=1C=NC2=C(C=CC=C2C=1)C RLXNCCMFGMORFD-UHFFFAOYSA-N 0.000 claims 1
• UDHYKSDZPGKEBP-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpent-4-en-2-yl)-7,8-difluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(=C)C)(C)NC(=O)C=1C=NC2=C(C(=CC=C2C=1)F)F UDHYKSDZPGKEBP-UHFFFAOYSA-N 0.000 claims 1
• GQKJCCBWMYAKOY-UHFFFAOYSA-N N-(2,4-dimethyl-1-phenylpentan-2-yl)-7,8-difluoroquinoline-3-carboxamide Chemical compound C(C1=CC=CC=C1)C(CC(C)C)(C)NC(=O)C=1C=NC2=C(C(=CC=C2C=1)F)F GQKJCCBWMYAKOY-UHFFFAOYSA-N 0.000 claims 1
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