JP2014523880A5 - - Google Patents
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- JP2014523880A5 JP2014523880A5 JP2014517113A JP2014517113A JP2014523880A5 JP 2014523880 A5 JP2014523880 A5 JP 2014523880A5 JP 2014517113 A JP2014517113 A JP 2014517113A JP 2014517113 A JP2014517113 A JP 2014517113A JP 2014523880 A5 JP2014523880 A5 JP 2014523880A5
- Authority
- JP
- Japan
- Prior art keywords
- difluoro
- difluorophenyl
- tetrazol
- optionally substituted
- propan
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 44
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 23
- 125000001188 haloalkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 125000004001 thioalkyl group Chemical group 0.000 claims 10
- 235000019000 fluorine Nutrition 0.000 claims 8
- -1 flutriaphor Chemical compound 0.000 claims 8
- 241000196324 Embryophyta Species 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 5
- 235000010290 biphenyl Nutrition 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims 5
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000001425 triazolyl group Chemical group 0.000 claims 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 4
- 241000894007 species Species 0.000 claims 4
- 241000209140 Triticum Species 0.000 claims 3
- 235000021307 Triticum Nutrition 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 244000005700 microbiome Species 0.000 claims 3
- OGJSRSSAVVZZNA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[4-(4-fluorophenyl)phenyl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1C=CC(=CC=1)C=1C=CC(F)=CC=1)(O)CN1C=NN=N1 OGJSRSSAVVZZNA-UHFFFAOYSA-N 0.000 claims 2
- 241000510928 Erysiphe necator Species 0.000 claims 2
- 241000223218 Fusarium Species 0.000 claims 2
- 241000131448 Mycosphaerella Species 0.000 claims 2
- 241000221300 Puccinia Species 0.000 claims 2
- 241000231139 Pyricularia Species 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000002538 fungal effect Effects 0.000 claims 2
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 239000000417 fungicide Substances 0.000 claims 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims 1
- ZAHUSXVPZMFMSF-UHFFFAOYSA-N 1,1-difluoro-2-(4-fluorophenyl)-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyrazin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(C(F)(F)C=1N=CC(=NC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 ZAHUSXVPZMFMSF-UHFFFAOYSA-N 0.000 claims 1
- BSWSAXNDRRRWHT-UHFFFAOYSA-N 1-(1,3-benzothiazol-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=1SC2=CC=CC=C2N=1)(O)CN1C=NN=N1 BSWSAXNDRRRWHT-UHFFFAOYSA-N 0.000 claims 1
- PRPKWVAYXRKYPZ-UHFFFAOYSA-N 1-(4-bromo-1,3-thiazol-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=1SC=C(Br)N=1)(O)CN1C=NN=N1 PRPKWVAYXRKYPZ-UHFFFAOYSA-N 0.000 claims 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims 1
- IJWUZGPWBQCMCV-UHFFFAOYSA-N 1-(5,6-dichloroquinolin-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=C2C=CC(Cl)=C(Cl)C2=CC=1)(O)CN1C=NN=N1 IJWUZGPWBQCMCV-UHFFFAOYSA-N 0.000 claims 1
- PQZSGYYELIGLCJ-UHFFFAOYSA-N 1-(5-bromothiophen-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=1SC(Br)=CC=1)(O)CN1C=NN=N1 PQZSGYYELIGLCJ-UHFFFAOYSA-N 0.000 claims 1
- QXDLOJRAQLRLBT-UHFFFAOYSA-N 1-(5-chloropyrazin-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(Cl)=NC=1)(O)CN1C=NN=N1 QXDLOJRAQLRLBT-UHFFFAOYSA-N 0.000 claims 1
- CRSUVPIGFCLECU-UHFFFAOYSA-N 1-(5-chloroquinolin-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=C2C=CC=C(Cl)C2=CC=1)(O)CN1C=NN=N1 CRSUVPIGFCLECU-UHFFFAOYSA-N 0.000 claims 1
- MSWUQKNAWRQPCE-UHFFFAOYSA-N 1-(5-chlorothiophen-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=1SC(Cl)=CC=1)(O)CN1C=NN=N1 MSWUQKNAWRQPCE-UHFFFAOYSA-N 0.000 claims 1
- SNJWBEVAANRMGD-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-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=1SC2=CC(Br)=CC=C2N=1)(O)CN1C=NN=N1 SNJWBEVAANRMGD-UHFFFAOYSA-N 0.000 claims 1
- GWVCFCRFDMCWAG-UHFFFAOYSA-N 1-(6-bromoquinolin-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=C2C=CC(Br)=CC2=CC=1)(O)CN1C=NN=N1 GWVCFCRFDMCWAG-UHFFFAOYSA-N 0.000 claims 1
- CGQRRXIQHKQABV-UHFFFAOYSA-N 1-(6-bromoquinoxalin-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=C2C=CC(Br)=CC2=NC=1)(O)CN1C=NN=N1 CGQRRXIQHKQABV-UHFFFAOYSA-N 0.000 claims 1
- VWIDQLCQMLJPJT-UHFFFAOYSA-N 1-(6-chloro-1,3-benzothiazol-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=1SC2=CC(Cl)=CC=C2N=1)(O)CN1C=NN=N1 VWIDQLCQMLJPJT-UHFFFAOYSA-N 0.000 claims 1
- DISWUHUIHBBZPN-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-1,1-difluoro-2-(4-fluorophenyl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 DISWUHUIHBBZPN-UHFFFAOYSA-N 0.000 claims 1
- NOFDPNWFRGLYTK-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-1,1-difluoro-2-(4-methoxyphenyl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC)=CC=C1C(O)(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)CN1N=NN=C1 NOFDPNWFRGLYTK-UHFFFAOYSA-N 0.000 claims 1
- QRKOVNZOQNNGJY-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-1,1-difluoro-2-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C(F)(F)F)C=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 QRKOVNZOQNNGJY-UHFFFAOYSA-N 0.000 claims 1
- DWWBHYCWKISDQJ-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-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=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NC=N1 DWWBHYCWKISDQJ-UHFFFAOYSA-N 0.000 claims 1
- FBMNHICXWINQQQ-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-4-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=C1 FBMNHICXWINQQQ-UHFFFAOYSA-N 0.000 claims 1
- SRBBDMDDBINJKI-UHFFFAOYSA-N 1-(6-chloroquinolin-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=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 SRBBDMDDBINJKI-UHFFFAOYSA-N 0.000 claims 1
- AQTFAULFKXBOEC-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1N=CN=N1 AQTFAULFKXBOEC-UHFFFAOYSA-N 0.000 claims 1
- VTBQSKCJQUNDHA-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,5-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C(F)=CC=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1N=CN=N1 VTBQSKCJQUNDHA-UHFFFAOYSA-N 0.000 claims 1
- UKPFJMNQOUIOFT-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-[2-chloro-4-(trifluoromethyl)phenyl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 UKPFJMNQOUIOFT-UHFFFAOYSA-N 0.000 claims 1
- XJBIYNPVUFIELG-UHFFFAOYSA-N 1-(6-chloroquinoxalin-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=C2C=CC(Cl)=CC2=NC=1)(O)CN1C=NN=N1 XJBIYNPVUFIELG-UHFFFAOYSA-N 0.000 claims 1
- CJJPANKYCQOBAK-UHFFFAOYSA-N 1-(7-chloroisoquinolin-3-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=CC2=CC(Cl)=CC=C2C=1)(O)CN1C=NN=N1 CJJPANKYCQOBAK-UHFFFAOYSA-N 0.000 claims 1
- RYUBZLWHLBOAIJ-UHFFFAOYSA-N 1-[5-(4-bromophenyl)pyrazin-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(=NC=1)C=1C=CC(Br)=CC=1)(O)CN1C=NN=N1 RYUBZLWHLBOAIJ-UHFFFAOYSA-N 0.000 claims 1
- SFANIAZLOAGMGY-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)pyrazin-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(=NC=1)C=1C=CC(Cl)=CC=1)(O)CN1C=NN=N1 SFANIAZLOAGMGY-UHFFFAOYSA-N 0.000 claims 1
- FUXCBKALBDKNQA-UHFFFAOYSA-N 1-[5-[4-(difluoromethoxy)phenyl]pyrazin-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(=NC=1)C=1C=CC(OC(F)F)=CC=1)(O)CN1C=NN=N1 FUXCBKALBDKNQA-UHFFFAOYSA-N 0.000 claims 1
- OWJJEBKOZTVUJO-UHFFFAOYSA-N 1-[6-(difluoromethyl)quinolin-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=C2C=CC(=CC2=CC=1)C(F)F)(O)CN1C=NN=N1 OWJJEBKOZTVUJO-UHFFFAOYSA-N 0.000 claims 1
- WDNZYDPCYQMVFY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(6-fluoroquinolin-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=C2C=CC(F)=CC2=CC=1)(O)CN1C=NN=N1 WDNZYDPCYQMVFY-UHFFFAOYSA-N 0.000 claims 1
- UZRGYSSSYMJPJN-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(6-fluoroquinoxalin-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=C2C=CC(F)=CC2=NC=1)(O)CN1C=NN=N1 UZRGYSSSYMJPJN-UHFFFAOYSA-N 0.000 claims 1
- DJMRCOHIQJQRNB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(6-methylquinolin-2-yl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC2=CC(C)=CC=C2N=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1C=NN=N1 DJMRCOHIQJQRNB-UHFFFAOYSA-N 0.000 claims 1
- SPXYZHSJGNFPNQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-fluorophenyl)pyrazin-2-yl]-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=NC=1)C=1C=CC(F)=CC=1)(O)CN1N=CN=N1 SPXYZHSJGNFPNQ-UHFFFAOYSA-N 0.000 claims 1
- JLHUZXNJGGGINI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-methoxyphenyl)pyrazin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=CN=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=N1 JLHUZXNJGGGINI-UHFFFAOYSA-N 0.000 claims 1
- MNNPKXJRKFWZAA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethyl]pyrazin-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(CCC=2C=CC(F)=CC=2)=NC=1)(O)CN1C=NN=N1 MNNPKXJRKFWZAA-UHFFFAOYSA-N 0.000 claims 1
- DUSGQISEKVGKFY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(CCC=2C=CC(F)=CC=2)=NC=1)(O)CN1N=CN=N1 DUSGQISEKVGKFY-UHFFFAOYSA-N 0.000 claims 1
- AKIJOMXPTBDWHL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethynyl]pyrazin-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(=NC=1)C#CC=1C=CC(F)=CC=1)(O)CN1C=NN=N1 AKIJOMXPTBDWHL-UHFFFAOYSA-N 0.000 claims 1
- LEKFFQGYDLBDCX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethynyl]pyrazin-2-yl]-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=NC=1)C#CC=1C=CC(F)=CC=1)(O)CN1N=CN=N1 LEKFFQGYDLBDCX-UHFFFAOYSA-N 0.000 claims 1
- JMBMKGWQEWYALI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[6-(4-fluorophenyl)pyridazin-3-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=NC(=CC=1)C=1C=CC(F)=CC=1)(O)CN1C=NN=N1 JMBMKGWQEWYALI-UHFFFAOYSA-N 0.000 claims 1
- UZYJYHPEBHBKRD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-pyrimidin-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=CN=1)(O)CN1C=NN=N1 UZYJYHPEBHBKRD-UHFFFAOYSA-N 0.000 claims 1
- GPLQUAMQMYCLMQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-quinolin-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=C2C=CC=CC2=CC=1)(O)CN1C=NN=N1 GPLQUAMQMYCLMQ-UHFFFAOYSA-N 0.000 claims 1
- FOZAIQXJYUGLJS-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-(1,3-thiazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1SC=CN=1)(O)CN1C=NN=N1 FOZAIQXJYUGLJS-UHFFFAOYSA-N 0.000 claims 1
- DCYAGIBHSJIZOZ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1C=CC(=CC=1)C=1C=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 DCYAGIBHSJIZOZ-UHFFFAOYSA-N 0.000 claims 1
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| AU2015231216B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
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| JP6623015B2 (ja) * | 2014-09-29 | 2019-12-18 | 国立研究開発法人理化学研究所 | 植物の耐塩性向上剤 |
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| LT3297998T (lt) | 2015-05-18 | 2020-06-10 | Viamet Pharmaceuticals (NC), Inc. | Priešgrybeliniai junginiai |
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2012
- 2012-06-20 EA EA201490088A patent/EA025266B1/ru not_active IP Right Cessation
- 2012-06-20 CN CN201280040551.XA patent/CN103857675A/zh active Pending
- 2012-06-20 CN CN201811257707.5A patent/CN109400594A/zh active Pending
- 2012-06-20 US US13/528,319 patent/US8883797B2/en active Active
- 2012-06-20 EP EP12801805.8A patent/EP2723730A4/en not_active Withdrawn
- 2012-06-20 EA EA201490052A patent/EA201490052A1/ru unknown
- 2012-06-20 PH PH1/2013/502622A patent/PH12013502622A1/en unknown
- 2012-06-20 WO PCT/US2012/043292 patent/WO2012177725A1/en not_active Ceased
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- 2012-06-20 JP JP2014517112A patent/JP6223329B2/ja not_active Expired - Fee Related
- 2012-06-20 AU AU2012273007A patent/AU2012273007A1/en not_active Abandoned
- 2012-06-20 CN CN201280040552.4A patent/CN103930418A/zh active Pending
- 2012-06-20 AU AU2012273004A patent/AU2012273004B2/en not_active Ceased
- 2012-06-20 JP JP2014517113A patent/JP2014523880A/ja active Pending
- 2012-06-20 US US13/528,283 patent/US8940735B2/en active Active
- 2012-06-20 EP EP12802142.5A patent/EP2723731B1/en not_active Not-in-force
- 2012-06-20 CA CA2838916A patent/CA2838916C/en not_active Expired - Fee Related
- 2012-06-20 KR KR1020147001619A patent/KR20140039059A/ko not_active Withdrawn
- 2012-06-20 WO PCT/US2012/043295 patent/WO2012177728A1/en not_active Ceased
- 2012-06-20 KR KR1020147001615A patent/KR101964195B1/ko not_active Expired - Fee Related
- 2012-06-20 IN IN286DEN2014 patent/IN2014DN00286A/en unknown
- 2012-06-20 MX MX2013015159A patent/MX2013015159A/es unknown
- 2012-06-22 AR ARP120102236A patent/AR094127A1/es not_active Application Discontinuation
- 2012-06-22 UY UY0001034156A patent/UY34156A/es not_active Application Discontinuation
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