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
- 241000087479 Pseudocercospora fijiensis Species 0.000 claims 1
- 241000567197 Puccinia graminis f. sp. tritici Species 0.000 claims 1
- 241001361634 Rhizoctonia Species 0.000 claims 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 claims 1
- 241000533281 Stagonospora Species 0.000 claims 1
- 241000510929 Uncinula Species 0.000 claims 1
- 241000221576 Uromyces Species 0.000 claims 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 claims 1
- 241000228452 Venturia inaequalis Species 0.000 claims 1
- 241001360088 Zymoseptoria tritici Species 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
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| PT3153020T (pt) | 2009-10-07 | 2019-02-26 | Dow Agrosciences Llc | Misturas fungicidas sinérgicas para o controlo de fungos em cereais |
| AU2012273004B2 (en) * | 2011-06-23 | 2017-04-13 | Mycovia Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| CN104136427B (zh) | 2012-01-20 | 2017-03-01 | 威尔金制药有限公司 | 金属酶抑制剂化合物 |
| UA114661C2 (uk) | 2012-12-28 | 2017-07-10 | Дау Аґросаєнсиз Елелсі | Синергічні фунгіцидні суміші для боротьби з грибковими хворобами злаків |
| BR112015015243B8 (pt) | 2012-12-31 | 2022-08-23 | Dow Agrosciences Llc | Composto contendo picolinamidas macrocíclicas, composição e método para controle e prevenção de doença em planta |
| WO2015100181A1 (en) | 2013-12-26 | 2015-07-02 | Dow Agrosciences Llc | Macrocyclic picolinamide compounds with fungicidal activity |
| WO2015100184A1 (en) | 2013-12-26 | 2015-07-02 | Dow Agrosciences Llc | Use of macrocyclic picolinamides as fungicides |
| AU2015231216B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| BR112016021257B1 (pt) * | 2014-03-19 | 2021-03-02 | Viamet Pharmaceuticals (NC), Inc. | 2-(2,4- difluorofenil-1,1-diflúor-1-(5-substituído-piridin-2-il)-3- (1h-tetrazol-1-il)propan-2-óis e processos para preparação e uso dos mesmos |
| EA201691648A1 (ru) | 2014-03-19 | 2017-01-30 | Ваймет Фармасьютикалс, Инк. | Способ получения противогрибковых соединений |
| AU2015231275B2 (en) * | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| EP3119756B9 (en) | 2014-03-19 | 2021-08-25 | Dow AgroSciences LLC | 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 |
| AU2015231270B2 (en) * | 2014-03-19 | 2019-03-07 | Viamet Pharmaceuticals (NC), 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 |
| US10017494B2 (en) | 2014-03-19 | 2018-07-10 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| CA2942972A1 (en) | 2014-03-19 | 2015-09-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Antifungal compound process |
| KR102151082B1 (ko) * | 2014-03-19 | 2020-09-03 | 더 유나이티드 스테이츠 오브 어메리카, 애즈 리프리젠티드 바이 더 시크리터리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비시스 | 항진균 화합물 제조방법 |
| JP6532480B2 (ja) | 2014-04-15 | 2019-06-19 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌剤としての金属酵素阻害剤化合物 |
| US9944664B2 (en) * | 2014-04-15 | 2018-04-17 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| US20150322051A1 (en) | 2014-05-06 | 2015-11-12 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| BR112017000169A2 (pt) | 2014-07-08 | 2017-10-31 | Dow Agrosciences Llc | picolinamidas macrocíclicas como fungicidas |
| BR112017000104A2 (pt) | 2014-07-08 | 2017-10-31 | Dow Agrosciences Llc | picolinamidas macrocíclicas como fungicidas |
| EP3240408B1 (en) | 2014-12-30 | 2020-04-08 | Dow Agrosciences LLC | Picolinamides with fungicidal activity |
| CN107105653A (zh) | 2014-12-30 | 2017-08-29 | 美国陶氏益农公司 | 杀真菌组合物 |
| NZ732812A (en) | 2014-12-30 | 2019-01-25 | Dow Agrosciences Llc | Use of picolinamides and other compounds as fungicides |
| BR122019023756B1 (pt) | 2014-12-30 | 2022-01-25 | Dow Agrosciences Llc | Composição para controle de um patógeno fúngico, e método para controle e prevenção de ataque fúngico em uma planta |
| AU2015374378B2 (en) | 2014-12-30 | 2018-02-15 | Dow Agrosciences Llc | Use of picolinamide compounds with fungicidal activity |
| BR112017013758B1 (pt) | 2014-12-30 | 2021-11-23 | Dow Agrosciences Llc | Compostos de picolinamida com atividade fungicida |
| PL3271347T3 (pl) | 2015-03-19 | 2022-11-21 | Mycovia Pharmaceuticals, Inc. | Związki przeciwgrzybicze i sposoby wytwarzania |
| KR102798709B1 (ko) | 2015-09-18 | 2025-04-23 | 마이코비아 파마슈티컬즈, 인코포레이티드 | 항진균 화합물 제조 방법 |
| EP3397629B1 (en) * | 2015-12-30 | 2023-04-19 | NQP 1598, Ltd. | Metalloenzyme inhibitor compounds |
| WO2018045010A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity |
| US10244754B2 (en) | 2016-08-30 | 2019-04-02 | Dow Agrosciences Llc | Picolinamide N-oxide compounds with fungicidal activity |
| WO2018044996A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Picolinamides as fungicides |
| WO2018044987A1 (en) | 2016-08-30 | 2018-03-08 | 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 |
| 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 |
| WO2018204438A1 (en) | 2017-05-02 | 2018-11-08 | Dow Agrosciences Llc | Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses |
| 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 |
| BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| US11639334B2 (en) | 2018-10-15 | 2023-05-02 | Corteva Agriscience Llc | Methods for synthesis of oxypicolinamides |
| CN114554848A (zh) | 2019-10-18 | 2022-05-27 | 科迪华农业科技有限责任公司 | 用于合成吡啶酰胺的方法 |
| 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 |
| TW202140445A (zh) * | 2020-01-17 | 2021-11-01 | 大陸商上海森輝醫藥有限公司 | 四氮唑類化合物的可藥用鹽及其結晶形式、製備方法和用途 |
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| DE3461637D1 (en) * | 1983-02-16 | 1987-01-22 | Pfizer Ltd | Triazole antifungal agents |
| GB8304282D0 (en) | 1983-02-16 | 1983-03-23 | Pfizer Ltd | 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 |
| US8987312B2 (en) * | 2008-07-09 | 2015-03-24 | The Scripps Research Institute | Alpha-keto heterocycles as FAAH inhibitors |
| CA2735693A1 (en) | 2008-09-03 | 2010-03-11 | Bayer Cropscience Ag | Use of fungicidal compound compositions for controlling certain rust fungi |
| CA2785898C (en) * | 2009-12-31 | 2018-07-03 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| JP5266430B2 (ja) * | 2010-04-24 | 2013-08-21 | 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 | 金属酵素阻害化合物 |
| AU2012273004B2 (en) * | 2011-06-23 | 2017-04-13 | Mycovia Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
-
2013
- 2013-01-18 EA EA201491386A patent/EA201491386A1/ru unknown
- 2013-01-18 BR BR112014017799A patent/BR112014017799A8/pt not_active IP Right Cessation
- 2013-01-18 US US14/373,304 patent/US9414596B2/en not_active Expired - Fee Related
- 2013-01-18 MX MX2014008729A patent/MX2014008729A/es unknown
- 2013-01-18 KR KR1020147023021A patent/KR20140116515A/ko not_active Withdrawn
- 2013-01-18 CN CN201380010205.1A patent/CN104135861A/zh active Pending
- 2013-01-18 CA CA2861341A patent/CA2861341A1/en not_active Abandoned
- 2013-01-18 WO PCT/US2013/022317 patent/WO2013110002A1/en not_active Ceased
- 2013-01-18 JP JP2014553493A patent/JP2015505538A/ja not_active Ceased
- 2013-01-18 EP EP13739106.6A patent/EP2804479A4/en not_active Withdrawn
- 2013-01-18 AU AU2013209520A patent/AU2013209520A1/en not_active Abandoned
- 2013-01-18 IN IN6812DEN2014 patent/IN2014DN06812A/en unknown
-
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 EC ECIEPI201414530A patent/ECSP14014530A/es unknown
- 2014-08-18 CR CR20140387A patent/CR20140387A/es unknown
-
2016
- 2016-12-15 JP JP2016243478A patent/JP2017110004A/ja active Pending
-
2019
- 2019-02-05 JP JP2019018600A patent/JP2019116476A/ja active Pending
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