ES2661849T3 - Piperidinpirazoles como fungicidas - Google Patents

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Publication number

ES2661849T3

ES2661849T3 ES12756492.0T ES12756492T ES2661849T3 ES 2661849 T3 ES2661849 T3 ES 2661849T3 ES 12756492 T ES12756492 T ES 12756492T ES 2661849 T3 ES2661849 T3 ES 2661849T3

Authority

ES

Spain

Prior art keywords

alkyl

phenyl

cycloalkyl

plants

haloalkyl

Prior art date

2011-09-15

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.)

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• 239000000417 fungicide Substances 0.000 title description 10
• -1 dihydronaphthalenyl Chemical group 0.000 claims abstract description 464
• 150000001875 compounds Chemical class 0.000 claims abstract description 111
• 125000001424 substituent group Chemical group 0.000 claims abstract description 77
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 61
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 37
• 239000001257 hydrogen Substances 0.000 claims abstract description 36
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 33
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 32
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 29
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 28
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 28
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 25
• 229910052736 halogen Chemical group 0.000 claims abstract description 25
• 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 24
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 23
• 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 23
• 150000002367 halogens Chemical group 0.000 claims abstract description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
• 239000001301 oxygen Substances 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 22
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 21
• 125000005347 halocycloalkyl group Chemical group 0.000 claims abstract description 21
• 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 20
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract description 19
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 18
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
• 239000011593 sulfur Substances 0.000 claims abstract description 15
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 14
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 13
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 13
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 13
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims abstract description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
• 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims abstract description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 10
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 9
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 9
• 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 9
• 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims abstract description 9
• 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims abstract description 8
• 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 8
• 125000005366 cycloalkylthio group Chemical group 0.000 claims abstract description 8
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
• 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 7
• 239000002184 metal Chemical class 0.000 claims abstract description 7
• 229910052751 metal Inorganic materials 0.000 claims abstract description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
• 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims abstract description 6
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 6
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 6
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 6
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 6
• 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims abstract description 6
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 6
• 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims abstract description 6
• 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims abstract description 6
• 125000006769 halocycloalkoxy group Chemical group 0.000 claims abstract description 6
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims abstract description 5
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 5
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract description 5
• 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract description 5
• 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims abstract description 5
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims abstract description 5
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 5
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 4
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 4
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims abstract description 4
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims abstract description 4
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims abstract description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 4
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims abstract description 4
• 125000004664 haloalkylsulfonylamino group Chemical group 0.000 claims abstract description 4
• 125000005292 haloalkynyloxy group Chemical group 0.000 claims abstract description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 3
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims abstract description 3
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 3
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims abstract description 3
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 3
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 3
• 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims abstract description 3
• 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims abstract description 3
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical group 0.000 claims abstract 9
• 238000000034 method Methods 0.000 claims description 103
• 239000000203 mixture Substances 0.000 claims description 91
• 241000233866 Fungi Species 0.000 claims description 35
• 230000009261 transgenic effect Effects 0.000 claims description 24
• 230000003032 phytopathogenic effect Effects 0.000 claims description 21
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 239000000463 material Substances 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
• 125000005336 allyloxy group Chemical group 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 239000004094 surface-active agent Substances 0.000 claims description 8
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 4
• 238000003898 horticulture Methods 0.000 claims description 3
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
• 125000006449 cycloalkyl cyclopropyl group Chemical group 0.000 claims 2
• 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims 1
• CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 1
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract description 2
• BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 abstract 1
• 125000005103 alkyl silyl group Chemical group 0.000 abstract 1
• 241000196324 Embryophyta Species 0.000 description 279
• 108090000623 proteins and genes Proteins 0.000 description 80
• 239000004480 active ingredient Substances 0.000 description 57
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
• 102000004169 proteins and genes Human genes 0.000 description 47
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 42
• 239000002904 solvent Substances 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 239000000243 solution Substances 0.000 description 23
• 238000009472 formulation Methods 0.000 description 22
• 230000000749 insecticidal effect Effects 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 239000003630 growth substance Substances 0.000 description 21
• 241000238631 Hexapoda Species 0.000 description 20
• 239000004009 herbicide Substances 0.000 description 20
• 240000008042 Zea mays Species 0.000 description 19
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 19
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 19
• 235000005822 corn Nutrition 0.000 description 19
• 201000010099 disease Diseases 0.000 description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 19
• 235000013399 edible fruits Nutrition 0.000 description 19
• 102000004190 Enzymes Human genes 0.000 description 18
• 108090000790 Enzymes Proteins 0.000 description 18
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 239000000126 substance Substances 0.000 description 18
• 230000015572 biosynthetic process Effects 0.000 description 17
• 230000009466 transformation Effects 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• 230000000694 effects Effects 0.000 description 16
• 238000005160 1H NMR spectroscopy Methods 0.000 description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 150000001345 alkine derivatives Chemical class 0.000 description 15
• 239000000460 chlorine Substances 0.000 description 15
• 229910052801 chlorine Inorganic materials 0.000 description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 15
• 230000002363 herbicidal effect Effects 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 238000003786 synthesis reaction Methods 0.000 description 14
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
• 229910052794 bromium Inorganic materials 0.000 description 13
• 238000003306 harvesting Methods 0.000 description 13
• 239000000047 product Substances 0.000 description 13
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
• 241000193388 Bacillus thuringiensis Species 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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• 239000002585 base Substances 0.000 description 12
• 229910052731 fluorine Inorganic materials 0.000 description 12
• XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 12
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• 229920000742 Cotton Polymers 0.000 description 11
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• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
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• 150000007513 acids Chemical class 0.000 description 10
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