BR112014005989B1 - compostos fungicidas piperidina-pirazoles, seus usos, método e composição para controlar fungos fitopatogênicos prejudiciais, e método para produzir composições - Google Patents

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Publication number

BR112014005989B1

BR112014005989B1 BR112014005989-6A BR112014005989A BR112014005989B1 BR 112014005989 B1 BR112014005989 B1 BR 112014005989B1 BR 112014005989 A BR112014005989 A BR 112014005989A BR 112014005989 B1 BR112014005989 B1 BR 112014005989B1

Authority

BR

Brazil

Prior art keywords

alkyl

symbol

plants

cycloalkyl

alkoxy

Prior art date

2011-09-15

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• 238000000034 method Methods 0.000 title claims abstract description 108
• 239000000203 mixture Substances 0.000 title claims abstract description 93
• 241000233866 Fungi Species 0.000 title claims abstract description 39
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
• 150000001875 compounds Chemical class 0.000 title claims description 119
• 230000003032 phytopathogenic effect Effects 0.000 title claims description 17
• 230000000855 fungicidal effect Effects 0.000 title description 7
• CXVWVEAHZKABIU-UHFFFAOYSA-N piperidine;1h-pyrazole Chemical compound C=1C=NNC=1.C1CCNCC1 CXVWVEAHZKABIU-UHFFFAOYSA-N 0.000 title description 2
• -1 piperidine pyrazoles Chemical class 0.000 claims abstract description 505
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 238000003898 horticulture Methods 0.000 claims abstract description 4
• 125000001424 substituent group Chemical group 0.000 claims description 79
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 125000001188 haloalkyl group Chemical group 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000003342 alkenyl group Chemical group 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 230000009261 transgenic effect Effects 0.000 claims description 23
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 17
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
• 229910052736 halogen Chemical group 0.000 claims description 17
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• 150000002367 halogens Chemical group 0.000 claims description 16
• 239000011593 sulfur Substances 0.000 claims description 16
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 14
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 13
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• 125000005336 allyloxy group Chemical group 0.000 claims description 9
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 9
• 229910052751 metal Inorganic materials 0.000 claims description 9
• 239000002184 metal Substances 0.000 claims description 9
• 150000002739 metals Chemical class 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
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• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
• 150000001204 N-oxides Chemical class 0.000 claims description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
• 239000000945 filler Substances 0.000 claims description 5
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 4
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 4
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
• 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 4
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
• 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
• 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
• 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 3
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 3
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 3
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 2
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims description 2
• 125000006769 halocycloalkoxy group Chemical group 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 11
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
• 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
• 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims 1
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
• 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims 1
• 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 1
• 239000000463 material Substances 0.000 abstract description 17
• 239000000417 fungicide Substances 0.000 abstract description 9
• 241001465754 Metazoa Species 0.000 abstract description 7
• 230000036541 health Effects 0.000 abstract description 5
• 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 abstract description 5
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 4
• 239000003905 agrochemical Substances 0.000 abstract description 4
• 150000004885 piperazines Chemical class 0.000 abstract description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 3
• 230000001717 pathogenic effect Effects 0.000 abstract 2
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• 230000008569 process Effects 0.000 description 61
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• 239000002904 solvent Substances 0.000 description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
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