JP2015505538A5 - - Google Patents
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- Publication number
- JP2015505538A5 JP2015505538A5 JP2014553493A JP2014553493A JP2015505538A5 JP 2015505538 A5 JP2015505538 A5 JP 2015505538A5 JP 2014553493 A JP2014553493 A JP 2014553493A JP 2014553493 A JP2014553493 A JP 2014553493A JP 2015505538 A5 JP2015505538 A5 JP 2015505538A5
- Authority
- JP
- Japan
- Prior art keywords
- difluorophenyl
- pyridin
- tetrazol
- difluoro
- phenyl
- Prior art date
- 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.)
- Ceased
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- -1 halo thioalkyl Chemical group 0.000 claims 28
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 240000008067 Cucumis sativus Species 0.000 claims 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims 6
- 241000233866 Fungi Species 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 241000196324 Embryophyta Species 0.000 claims 5
- 244000052769 pathogen Species 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- IDUYJRXRDSPPRC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 IDUYJRXRDSPPRC-UHFFFAOYSA-N 0.000 claims 4
- 241000209140 Triticum Species 0.000 claims 4
- 235000021307 Triticum Nutrition 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 230000001717 pathogenic effect Effects 0.000 claims 4
- 241000510928 Erysiphe necator Species 0.000 claims 3
- 241000228453 Pyrenophora Species 0.000 claims 3
- 241001533598 Septoria Species 0.000 claims 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 3
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 3
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 3
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims 3
- IEYCWUALSWPHDI-UHFFFAOYSA-N 1-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenyl]-2,2,2-trifluoroethanone Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)C(=O)C(F)(F)F)(O)CN1C=NN=N1 IEYCWUALSWPHDI-UHFFFAOYSA-N 0.000 claims 2
- GNIKWJWEACQTNW-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(Cl)C=CC=1)(O)CN1C=NN=N1 GNIKWJWEACQTNW-UHFFFAOYSA-N 0.000 claims 2
- QFSIEMVDJIQESH-UHFFFAOYSA-N 1-[5-(4-chloro-3-fluorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(F)C(Cl)=CC=1)(O)CN1C=NN=N1 QFSIEMVDJIQESH-UHFFFAOYSA-N 0.000 claims 2
- BNRLEARACNMGQQ-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(Cl)=CC=1)(O)CN1C=NN=N1 BNRLEARACNMGQQ-UHFFFAOYSA-N 0.000 claims 2
- SGIOKLOTIKJJFS-UHFFFAOYSA-N 1-[5-[3-(difluoromethoxy)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(OC(F)F)C=CC=1)(O)CN1C=NN=N1 SGIOKLOTIKJJFS-UHFFFAOYSA-N 0.000 claims 2
- LTGBNLMVVAFZGT-UHFFFAOYSA-N 1-[5-[4-(difluoromethoxy)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)F)=CC=1)(O)CN1C=NN=N1 LTGBNLMVVAFZGT-UHFFFAOYSA-N 0.000 claims 2
- GSIBKGBPHNSCOU-UHFFFAOYSA-N 1-[5-[4-(difluoromethylsulfanyl)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(SC(F)F)=CC=1)(O)CN1C=NN=N1 GSIBKGBPHNSCOU-UHFFFAOYSA-N 0.000 claims 2
- BLPPSIFFRCQAID-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-phenylpyridin-2-yl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC=CC=1)(O)CN1C=NN=N1 BLPPSIFFRCQAID-UHFFFAOYSA-N 0.000 claims 2
- XJXWVRYXVARTIL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-fluorophenyl)pyridin-2-yl]-3-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(F)=CC=1)(O)CN1C=NC=N1 XJXWVRYXVARTIL-UHFFFAOYSA-N 0.000 claims 2
- YTYDYXBYPZKLBW-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCC(F)(F)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 YTYDYXBYPZKLBW-UHFFFAOYSA-N 0.000 claims 2
- YQTJCWNNHNJRAY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[4-[(2-methylpropan-2-yl)oxy]phenyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC(C)(C)C)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 YQTJCWNNHNJRAY-UHFFFAOYSA-N 0.000 claims 2
- MSRICOSVBSYAJO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NC=N1 MSRICOSVBSYAJO-UHFFFAOYSA-N 0.000 claims 2
- JJHAQEOFFYLRAX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NC=N1 JJHAQEOFFYLRAX-UHFFFAOYSA-N 0.000 claims 2
- XJOUOULZTJKLNL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1h-pyrazol-5-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CC=1C=CNN=1 XJOUOULZTJKLNL-UHFFFAOYSA-N 0.000 claims 2
- HSOHUDGZYOVUTH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[3-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(OC(F)(F)F)C=CC=1)(O)CN1C=NN=N1 HSOHUDGZYOVUTH-UHFFFAOYSA-N 0.000 claims 2
- CAXYCUMJWGYZCQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(C=CC=1)C(F)(F)F)(O)CN1C=NN=N1 CAXYCUMJWGYZCQ-UHFFFAOYSA-N 0.000 claims 2
- NGSZMSSFJMJEPD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethyl)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(CC(F)(F)F)=CC=1)(O)CN1C=NN=N1 NGSZMSSFJMJEPD-UHFFFAOYSA-N 0.000 claims 2
- IBQKNYMGTNJJGD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethylsulfanyl)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(SCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 IBQKNYMGTNJJGD-UHFFFAOYSA-N 0.000 claims 2
- JBDKQTLQCWIBHU-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(3,3,3-trifluoropropoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 JBDKQTLQCWIBHU-UHFFFAOYSA-N 0.000 claims 2
- NCEHACHJIXJSPD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 NCEHACHJIXJSPD-UHFFFAOYSA-N 0.000 claims 2
- WJGQBRYSRQIYNV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)C(F)(F)F)(O)CN1C=NN=N1 WJGQBRYSRQIYNV-UHFFFAOYSA-N 0.000 claims 2
- GJRJJAXJYBRRHV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCC(F)(F)F)=CC=1)(O)CN1N=CN=N1 GJRJJAXJYBRRHV-UHFFFAOYSA-N 0.000 claims 2
- GJSQDETZKLKYHM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(triazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=CN=N1 GJSQDETZKLKYHM-UHFFFAOYSA-N 0.000 claims 2
- UHZQCOJUZBONSC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-(2,5-difluorophenyl)pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C(=CC=C(F)C=1)F)(O)CN1C=NN=N1 UHZQCOJUZBONSC-UHFFFAOYSA-N 0.000 claims 2
- BOCNJXGUWFXJLX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-(3,4-difluorophenyl)pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(F)C(F)=CC=1)(O)CN1C=NN=N1 BOCNJXGUWFXJLX-UHFFFAOYSA-N 0.000 claims 2
- QBUDANSQCYSGLX-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 QBUDANSQCYSGLX-UHFFFAOYSA-N 0.000 claims 2
- PDUNABKLLIZVMV-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenol Chemical compound OC1=CC=CC(C=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 PDUNABKLLIZVMV-UHFFFAOYSA-N 0.000 claims 2
- DBTMJZFDSGXRMQ-UHFFFAOYSA-N 4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 DBTMJZFDSGXRMQ-UHFFFAOYSA-N 0.000 claims 2
- 235000017060 Arachis glabrata Nutrition 0.000 claims 2
- 244000105624 Arachis hypogaea Species 0.000 claims 2
- 235000010777 Arachis hypogaea Nutrition 0.000 claims 2
- 235000018262 Arachis monticola Nutrition 0.000 claims 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims 2
- 241001480060 Blumeria Species 0.000 claims 2
- 241001157813 Cercospora Species 0.000 claims 2
- 241000221785 Erysiphales Species 0.000 claims 2
- 241000221787 Erysiphe Species 0.000 claims 2
- 241000223218 Fusarium Species 0.000 claims 2
- 241000592921 Helminthosporium Species 0.000 claims 2
- 206010027146 Melanoderma Diseases 0.000 claims 2
- 241000221300 Puccinia Species 0.000 claims 2
- 241000231139 Pyricularia Species 0.000 claims 2
- 241000173767 Ramularia Species 0.000 claims 2
- 235000021536 Sugar beet Nutrition 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- HZLNQXPXQPWTKY-UHFFFAOYSA-N ethyl 2-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenoxy]-2,2-difluoroacetate Chemical compound C1=CC(OC(F)(F)C(=O)OCC)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 HZLNQXPXQPWTKY-UHFFFAOYSA-N 0.000 claims 2
- 244000053095 fungal pathogen Species 0.000 claims 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- ZLJNVYHHBJHWCQ-UHFFFAOYSA-N n-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenyl]-2,2,2-trifluoroacetamide Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(NC(=O)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 ZLJNVYHHBJHWCQ-UHFFFAOYSA-N 0.000 claims 2
- 235000020232 peanut Nutrition 0.000 claims 2
- FMHFVGODKSOEKV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(OCC(F)(F)F)C=C1 FMHFVGODKSOEKV-UHFFFAOYSA-N 0.000 claims 1
- HSUXUELXFIFBIT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 HSUXUELXFIFBIT-UHFFFAOYSA-N 0.000 claims 1
- JVHZFKDSOUQLNB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 JVHZFKDSOUQLNB-UHFFFAOYSA-N 0.000 claims 1
- XAFSRHUAOWTMSL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-3-[5-(4-fluorophenyl)pyridin-2-yl]-1-(tetrazol-1-yl)butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(F)C=C1 XAFSRHUAOWTMSL-UHFFFAOYSA-N 0.000 claims 1
- KYMREFHKHDOGRO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-3-[5-(4-fluorophenyl)pyridin-2-yl]-1-(tetrazol-2-yl)butan-2-ol Chemical compound N1=CN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(F)C=C1 KYMREFHKHDOGRO-UHFFFAOYSA-N 0.000 claims 1
- PQEHIYKEYOVAFU-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(Cl)C=C1 PQEHIYKEYOVAFU-UHFFFAOYSA-N 0.000 claims 1
- WCLFRXGODMAGSI-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(C=CC=1)C#N)(O)CN1C=NN=N1 WCLFRXGODMAGSI-UHFFFAOYSA-N 0.000 claims 1
- HKIZMJLDZKXRKA-UHFFFAOYSA-N 4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)C#N)(O)CN1C=NN=N1 HKIZMJLDZKXRKA-UHFFFAOYSA-N 0.000 claims 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims 1
- 241000223600 Alternaria Species 0.000 claims 1
- 241000193738 Bacillus anthracis Species 0.000 claims 1
- 241001480061 Blumeria graminis Species 0.000 claims 1
- 241001465180 Botrytis Species 0.000 claims 1
- 241000530549 Cercospora beticola Species 0.000 claims 1
- 241000222290 Cladosporium Species 0.000 claims 1
- 241000306559 Exserohilum Species 0.000 claims 1
- 241000221557 Gymnosporangium Species 0.000 claims 1
- 241000283160 Inia Species 0.000 claims 1
- 240000008790 Musa x paradisiaca Species 0.000 claims 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 claims 1
- 241000131448 Mycosphaerella Species 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 241000228143 Penicillium Species 0.000 claims 1
- 241000555275 Phaeosphaeria Species 0.000 claims 1
- 241000440444 Phakopsora Species 0.000 claims 1
- 241000896242 Podosphaera Species 0.000 claims 1
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| CA2894551A1 (en) | 2012-12-31 | 2014-07-03 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| EP3099170A4 (en) | 2013-12-26 | 2017-06-21 | Dow AgroSciences LLC | Use of macrocyclic picolinamides as fungicides |
| WO2015100181A1 (en) | 2013-12-26 | 2015-07-02 | Dow Agrosciences Llc | Macrocyclic picolinamide compounds with fungicidal activity |
| US9914726B2 (en) | 2014-03-19 | 2018-03-13 | Vps-3, Inc. | 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ols and processes for their preparation |
| JP2017509646A (ja) * | 2014-03-19 | 2017-04-06 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| CN109678791B (zh) * | 2014-03-19 | 2022-07-01 | 美国陶氏益农公司 | 1-(2,4-二氟苯)-2,2-二氟-2-(5-取代吡啶-2-基)乙酮及制备方法 |
| US10196375B2 (en) | 2014-03-19 | 2019-02-05 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP2017507991A (ja) * | 2014-03-19 | 2017-03-23 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| CA2942968C (en) * | 2014-03-19 | 2022-03-15 | William J. Hoekstra | Antifungal compound process |
| US10017494B2 (en) | 2014-03-19 | 2018-07-10 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| AU2015231270B2 (en) * | 2014-03-19 | 2019-03-07 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
| WO2015143154A1 (en) | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| JP6572234B2 (ja) * | 2014-03-19 | 2019-09-04 | ヴィアメット ファーマスーティカルズ（エヌシー），インコーポレイテッド | 抗真菌化合物の調製方法 |
| US9663491B2 (en) | 2014-04-15 | 2017-05-30 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| CA2945674A1 (en) * | 2014-04-15 | 2015-10-22 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| US20150322051A1 (en) | 2014-05-06 | 2015-11-12 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| WO2016007531A1 (en) | 2014-07-08 | 2016-01-14 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| CN106470982A (zh) | 2014-07-08 | 2017-03-01 | 美国陶氏益农公司 | 作为杀真菌剂的大环吡啶酰胺 |
| EP3808181A1 (en) * | 2014-12-30 | 2021-04-21 | Dow AgroSciences LLC | Use of picolinamide compounds as fungicides |
| AU2015374379B2 (en) | 2014-12-30 | 2018-10-04 | Dow Agrosciences Llc | Picolinamides as fungicides |
| MX2017008418A (es) | 2014-12-30 | 2017-09-28 | Dow Agrosciences Llc | Picolinamidas con actividad fungicida. |
| RU2704867C2 (ru) | 2014-12-30 | 2019-10-31 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Применение соединений пиколинамида с фунгицидным действием |
| CN107205398B (zh) | 2014-12-30 | 2020-08-21 | 美国陶氏益农公司 | 具有杀真菌活性的吡啶酰胺化合物 |
| UA121763C2 (uk) | 2014-12-30 | 2020-07-27 | Дау Аґросаєнсиз Елелсі | Фунгіцидні сполуки |
| CN107428724B (zh) | 2015-03-19 | 2021-07-02 | 迈科维亚医药公司 | 抗真菌化合物及制备方法 |
| BR112018005194B1 (pt) | 2015-09-18 | 2022-11-08 | Vps-3, Inc | Processo para preparar um composto antifúngico |
| MX376201B (es) * | 2015-12-30 | 2025-03-07 | Nqp 1598 Ltd | Compuestos inhibidores de metaloenzima. |
| US10111432B2 (en) | 2016-08-30 | 2018-10-30 | Dow Agrosciences Llc | Picolinamide N-oxide compounds with fungicidal activity |
| WO2018045010A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity |
| US10173982B2 (en) | 2016-08-30 | 2019-01-08 | Dow Agrosciences Llc | Picolinamides as fungicides |
| US10231452B2 (en) | 2016-08-30 | 2019-03-19 | Dow Agrosciences Llc | Thiopicolinamide compounds with fungicidal activity |
| BR102018000183B1 (pt) | 2017-01-05 | 2023-04-25 | Dow Agrosciences Llc | Picolinamidas, composição para controle de um patógeno fúngico, e método para controle e prevenção de um ataque por fungos em uma planta |
| EP3580218A1 (en) * | 2017-02-08 | 2019-12-18 | Bayer CropScience Aktiengesellschaft | Novel triazole derivatives |
| CN110996665B (zh) | 2017-05-02 | 2021-10-26 | 陶氏益农公司 | 无环吡啶酰胺化合物作为针对草坪草上的真菌病害的杀真菌剂的用途 |
| TWI774761B (zh) | 2017-05-02 | 2022-08-21 | 美商科迪華農業科技有限責任公司 | 用於穀物中的真菌防治之協同性混合物 |
| TW201842851A (zh) | 2017-05-02 | 2018-12-16 | 美商陶氏農業科學公司 | 用於穀類中的真菌防治之協同性混合物 |
| BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| EP3866597A4 (en) | 2018-10-15 | 2022-06-29 | Corteva Agriscience LLC | Methods for sythesis of oxypicolinamides |
| US12281076B2 (en) | 2019-10-18 | 2025-04-22 | Corteva Agriscience Llc | Process for synthesis of picolinamides |
| CN110981810A (zh) * | 2019-12-19 | 2020-04-10 | 东莞市维琪科技有限公司 | 一种脱羧肌肽的合成方法 |
| WO2021143811A1 (zh) * | 2020-01-17 | 2021-07-22 | 上海森辉医药有限公司 | 四氮唑类化合物的可药用盐及其结晶形式、制备方法和用途 |
| WO2026006142A1 (en) * | 2024-06-24 | 2026-01-02 | The United States Of America, As Represented By The Secretary, Dept. Of Health And Human Services | Azole compounds useful as inhibitors of voltage-dependent anion channel oligomerization |
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| GB8304282D0 (en) * | 1983-02-16 | 1983-03-23 | Pfizer Ltd | Antifungal agents |
| DE3461637D1 (en) * | 1983-02-16 | 1987-01-22 | Pfizer Ltd | Triazole antifungal agents |
| US5358939A (en) * | 1992-06-25 | 1994-10-25 | Rohm And Haas Company | Fungicidal 2-aryl-2,2-disubstituted ethyl-1,2,4-triazoles |
| CN1187756A (zh) * | 1995-06-16 | 1998-07-15 | 诺瓦提斯公司 | 保护作物的组合物 |
| MY115814A (en) * | 1995-06-16 | 2003-09-30 | Bayer Ip Gmbh | Crop protection compositions |
| JP2006143593A (ja) * | 2004-11-16 | 2006-06-08 | Hokko Chem Ind Co Ltd | Ｎ−ベンジルテトラゾール誘導体および農園芸用殺菌剤 |
| WO2010005572A2 (en) * | 2008-07-09 | 2010-01-14 | The Scripps Research Institute | Alpha-keto heterocycles as faah inhibitors |
| NZ591428A (en) * | 2008-09-03 | 2013-07-26 | Bayer Cropscience Ag | Use of bixafen and fluoxastrobin and/or trifloxystrobin for controlling rust in soy bean plants |
| US8987315B2 (en) * | 2009-12-31 | 2015-03-24 | Innocrin Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| SI2563771T1 (sl) * | 2010-04-24 | 2016-05-31 | Viamet Pharmaceuticals, Inc. | Spojine inhibitorjev metaloencimov |
| JP2014523880A (ja) * | 2011-06-23 | 2014-09-18 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 金属酵素化合物 |
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- 2013-01-18 WO PCT/US2013/022317 patent/WO2013110002A1/en not_active Ceased
- 2013-01-18 BR BR112014017799A patent/BR112014017799A8/pt not_active IP Right Cessation
- 2013-01-18 CA CA2861341A patent/CA2861341A1/en not_active Abandoned
- 2013-01-18 US US14/373,304 patent/US9414596B2/en not_active Expired - Fee Related
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- 2013-01-18 MX MX2014008729A patent/MX2014008729A/es unknown
- 2013-01-18 KR KR1020147023021A patent/KR20140116515A/ko not_active Withdrawn
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2014
- 2014-07-17 CL CL2014001892A patent/CL2014001892A1/es unknown
- 2014-07-18 PH PH12014501653A patent/PH12014501653A1/en unknown
- 2014-08-14 CO CO14178605A patent/CO7111289A2/es not_active Application Discontinuation
- 2014-08-18 CR CR20140387A patent/CR20140387A/es unknown
- 2014-08-18 EC ECIEPI201414530A patent/ECSP14014530A/es unknown
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2016
- 2016-12-15 JP JP2016243478A patent/JP2017110004A/ja active Pending
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2019
- 2019-02-05 JP JP2019018600A patent/JP2019116476A/ja active Pending
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