JP2012519693A5 - - Google Patents
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- Publication number
- JP2012519693A5 JP2012519693A5 JP2011553063A JP2011553063A JP2012519693A5 JP 2012519693 A5 JP2012519693 A5 JP 2012519693A5 JP 2011553063 A JP2011553063 A JP 2011553063A JP 2011553063 A JP2011553063 A JP 2011553063A JP 2012519693 A5 JP2012519693 A5 JP 2012519693A5
- Authority
- JP
- Japan
- Prior art keywords
- dimethyl
- pyrazol
- alkyl
- independently
- difluorophenyl
- 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.)
- Granted
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- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 21
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 12
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 150000001721 carbon Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004434 sulfur atom Chemical group 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 6
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 2
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 2
- DMBVWPWLMUNZCO-UHFFFAOYSA-N 4-(2,6-difluoro-4-methoxyphenyl)-2,5-dimethyl-n-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C(=CC(F)=CC=2F)F)N(C)N=C1C DMBVWPWLMUNZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- VXXSVCZAHLUQEJ-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-[4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1C(O)C1=CC=C(F)C=C1Br VXXSVCZAHLUQEJ-UHFFFAOYSA-N 0.000 claims 1
- KHQNYTMRFDRULL-UHFFFAOYSA-N (2-chloro-4,6-difluorophenyl)-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1C(O)C1=C(F)C=C(F)C=C1Cl KHQNYTMRFDRULL-UHFFFAOYSA-N 0.000 claims 1
- VYRMNTABYYNYHW-UHFFFAOYSA-N (4-chloro-2,6-difluorophenyl)-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1C(O)C1=C(F)C=C(Cl)C=C1F VYRMNTABYYNYHW-UHFFFAOYSA-N 0.000 claims 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- XIUXHKYVNPGCEP-UHFFFAOYSA-N 3-bromo-4-[4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Br XIUXHKYVNPGCEP-UHFFFAOYSA-N 0.000 claims 1
- AWBRZFXUAUARTI-UHFFFAOYSA-N 3-chloro-4-[4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Cl AWBRZFXUAUARTI-UHFFFAOYSA-N 0.000 claims 1
- NTWXHOHUZNUBGG-UHFFFAOYSA-N 3-chloro-4-[4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Cl NTWXHOHUZNUBGG-UHFFFAOYSA-N 0.000 claims 1
- RHXPXUWLNBCVEP-UHFFFAOYSA-N 3-chloro-4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1Cl RHXPXUWLNBCVEP-UHFFFAOYSA-N 0.000 claims 1
- GNNSNXJRJGUOFW-UHFFFAOYSA-N 3-chloro-4-[5-(2-chloro-4,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]benzonitrile Chemical compound C=1C=C(C#N)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl GNNSNXJRJGUOFW-UHFFFAOYSA-N 0.000 claims 1
- DKTYKODJDGLPEN-UHFFFAOYSA-N 3-chloro-4-[5-(4-chloro-2,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]benzonitrile Chemical compound C=1C=C(C#N)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F DKTYKODJDGLPEN-UHFFFAOYSA-N 0.000 claims 1
- XICXFPPCHFGZAG-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-2,5-dimethyl-n-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1F XICXFPPCHFGZAG-UHFFFAOYSA-N 0.000 claims 1
- JPULADNQXLGRKU-UHFFFAOYSA-N 4-(2,6-difluoro-4-methoxyphenyl)-n-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C(=CC(F)=CC=2)F)N(C)N=C1C JPULADNQXLGRKU-UHFFFAOYSA-N 0.000 claims 1
- KIULVEFSDWGFEQ-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-2,5-dimethyl-n-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1F KIULVEFSDWGFEQ-UHFFFAOYSA-N 0.000 claims 1
- MVCXZBKZESDLBY-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-n-(4-chloro-2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F MVCXZBKZESDLBY-UHFFFAOYSA-N 0.000 claims 1
- CQCKUFBAPXFDHZ-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-2,5-dimethyl-n-(2,4,6-trifluorophenyl)pyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1F CQCKUFBAPXFDHZ-UHFFFAOYSA-N 0.000 claims 1
- VKBIFWCNUMRFAD-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-n-(2,4-dichloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1Cl VKBIFWCNUMRFAD-UHFFFAOYSA-N 0.000 claims 1
- JVBZXENYGMUMPI-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-n-(2,6-dichloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(Cl)C=C(F)C=C1Cl JVBZXENYGMUMPI-UHFFFAOYSA-N 0.000 claims 1
- OJTSHHXIWDLHGO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-n-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=CC=C1F OJTSHHXIWDLHGO-UHFFFAOYSA-N 0.000 claims 1
- WLLBTGPVVUDNIM-UHFFFAOYSA-N 4-[4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3-fluorobenzonitrile Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1F WLLBTGPVVUDNIM-UHFFFAOYSA-N 0.000 claims 1
- WXHDEWKACNCFQQ-UHFFFAOYSA-N 4-[4-(2-bromo-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1OC1=C(F)C=C(C#N)C=C1F WXHDEWKACNCFQQ-UHFFFAOYSA-N 0.000 claims 1
- VDBLUBUZHAZTHA-UHFFFAOYSA-N 4-[4-(2-bromo-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(Br)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1F VDBLUBUZHAZTHA-UHFFFAOYSA-N 0.000 claims 1
- DSMGHOLXQLQVMA-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-2,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=CC(F)=C(C#N)C=C1F DSMGHOLXQLQVMA-UHFFFAOYSA-N 0.000 claims 1
- OFNRVDXZQMDYER-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=C(F)C=C(C#N)C=C1F OFNRVDXZQMDYER-UHFFFAOYSA-N 0.000 claims 1
- RAKKOIQLYSDCJT-UHFFFAOYSA-N 4-[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]oxy-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1OC1=CC=C(C#N)C=C1F RAKKOIQLYSDCJT-UHFFFAOYSA-N 0.000 claims 1
- GQMGMVRAMWNLHW-UHFFFAOYSA-N 4-[5-(2-chloro-4,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]-3-fluorobenzonitrile Chemical compound C=1C=C(C#N)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl GQMGMVRAMWNLHW-UHFFFAOYSA-N 0.000 claims 1
- GQUSTSWMNBDBJG-UHFFFAOYSA-N 4-[5-(4-chloro-2,6-difluoroanilino)-1,3-dimethylpyrazol-4-yl]-3-fluorobenzonitrile Chemical compound C=1C=C(C#N)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F GQUSTSWMNBDBJG-UHFFFAOYSA-N 0.000 claims 1
- BXVAVILFNGHERL-UHFFFAOYSA-N 4-[[4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]amino]-3,5-difluorobenzonitrile Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(C#N)C=C1F BXVAVILFNGHERL-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- GNBGNFVTOFWLSA-UHFFFAOYSA-N [4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]-(2,4-difluorophenyl)methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1C(O)C1=CC=C(F)C=C1F GNBGNFVTOFWLSA-UHFFFAOYSA-N 0.000 claims 1
- KKZUQQVWIKDTJZ-UHFFFAOYSA-N [4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-yl]methanol Chemical compound ClC1=C(C=CC(=C1)F)C=1C(=NN(C=1CO)C)C KKZUQQVWIKDTJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- KAEDTPSBWDVHHS-UHFFFAOYSA-N n,4-bis(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Cl KAEDTPSBWDVHHS-UHFFFAOYSA-N 0.000 claims 1
- ZPTPYNOCNLVTNU-UHFFFAOYSA-N n-(2,4-dichloro-6-fluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1Cl ZPTPYNOCNLVTNU-UHFFFAOYSA-N 0.000 claims 1
- FJFIHSRMQYTTPH-UHFFFAOYSA-N n-(2,6-dichloro-4-fluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(Cl)C=C(F)C=C1Cl FJFIHSRMQYTTPH-UHFFFAOYSA-N 0.000 claims 1
- RPQFJJKMVQMNAZ-UHFFFAOYSA-N n-(2,6-dichloro-4-fluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(Cl)C=C(F)C=C1Cl RPQFJJKMVQMNAZ-UHFFFAOYSA-N 0.000 claims 1
- RUVHNVSOOAVPJV-UHFFFAOYSA-N n-(2,6-difluoro-4-methoxyphenyl)-4-(3,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1NC1=C(C=2C=C(F)C(F)=CC=2)C(C)=NN1C RUVHNVSOOAVPJV-UHFFFAOYSA-N 0.000 claims 1
- PWGZAQWMMSWZHI-UHFFFAOYSA-N n-(2-bromo-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br PWGZAQWMMSWZHI-UHFFFAOYSA-N 0.000 claims 1
- VYZCGVAERODZMO-UHFFFAOYSA-N n-(2-bromo-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br VYZCGVAERODZMO-UHFFFAOYSA-N 0.000 claims 1
- OJWPZXSMQGXWDP-UHFFFAOYSA-N n-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br OJWPZXSMQGXWDP-UHFFFAOYSA-N 0.000 claims 1
- IZULPBUDCQEXJP-UHFFFAOYSA-N n-(2-bromo-4,6-difluorophenyl)-4-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Br IZULPBUDCQEXJP-UHFFFAOYSA-N 0.000 claims 1
- JUZPPCLWIDRLOD-UHFFFAOYSA-N n-(2-bromo-4-fluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Br JUZPPCLWIDRLOD-UHFFFAOYSA-N 0.000 claims 1
- BPNKKYDDFRFQEJ-UHFFFAOYSA-N n-(2-bromo-4-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Br BPNKKYDDFRFQEJ-UHFFFAOYSA-N 0.000 claims 1
- INFARVMXVOIJBK-UHFFFAOYSA-N n-(2-chloro-4,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl INFARVMXVOIJBK-UHFFFAOYSA-N 0.000 claims 1
- DPNWUIPDHAQECH-UHFFFAOYSA-N n-(2-chloro-4,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl DPNWUIPDHAQECH-UHFFFAOYSA-N 0.000 claims 1
- NELBALCXLWXLGI-UHFFFAOYSA-N n-(2-chloro-4,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(F)C=C1Cl NELBALCXLWXLGI-UHFFFAOYSA-N 0.000 claims 1
- HLRSVYVMAUGUEA-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C(=CC(F)=CC=2)Cl)N(C)N=C1C HLRSVYVMAUGUEA-UHFFFAOYSA-N 0.000 claims 1
- RXNUUCJQIFQLIM-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-4-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=CC=C(F)C=C1Cl RXNUUCJQIFQLIM-UHFFFAOYSA-N 0.000 claims 1
- QRUJTALPKCMJFC-UHFFFAOYSA-N n-(4-bromo-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Br)C=C1F QRUJTALPKCMJFC-UHFFFAOYSA-N 0.000 claims 1
- CASOODRLVWPKCS-UHFFFAOYSA-N n-(4-bromo-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Br)C=C1F CASOODRLVWPKCS-UHFFFAOYSA-N 0.000 claims 1
- ZPBTUAPAZAPRNV-UHFFFAOYSA-N n-(4-bromo-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Br)C=C1F ZPBTUAPAZAPRNV-UHFFFAOYSA-N 0.000 claims 1
- ZASNAGRZUWHOAF-UHFFFAOYSA-N n-(4-chloro-2,6-difluorophenyl)-4-(2,4-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F ZASNAGRZUWHOAF-UHFFFAOYSA-N 0.000 claims 1
- LOSLNCQXNBXLLF-UHFFFAOYSA-N n-(4-chloro-2,6-difluorophenyl)-4-(2,6-difluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC=1C=CC=C(F)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F LOSLNCQXNBXLLF-UHFFFAOYSA-N 0.000 claims 1
- QKEKUMRXLOHZQJ-UHFFFAOYSA-N n-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-2,5-dimethylpyrazol-3-amine Chemical compound C=1C=C(F)C=C(Cl)C=1C=1C(C)=NN(C)C=1NC1=C(F)C=C(Cl)C=C1F QKEKUMRXLOHZQJ-UHFFFAOYSA-N 0.000 claims 1
- OPZOZYIDZMWTER-UHFFFAOYSA-N n-(4-chlorophenyl)-4-(2,6-difluoro-4-methoxyphenyl)-2,5-dimethylpyrazol-3-amine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(NC=2C=CC(Cl)=CC=2)N(C)N=C1C OPZOZYIDZMWTER-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
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| PCT/US2010/026003 WO2010101973A1 (en) | 2009-03-03 | 2010-03-03 | Fungicidal pyrazoles |
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| JP2016252244A Division JP2017081965A (ja) | 2009-03-03 | 2016-12-27 | 殺菌・殺カビ性ピラゾール |
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| AR075713A1 (es) * | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| TW201245155A (en) | 2010-09-01 | 2012-11-16 | Du Pont | Fungicidal pyrazoles |
| TWI504350B (zh) * | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TWI568721B (zh) * | 2012-02-01 | 2017-02-01 | 杜邦股份有限公司 | 殺真菌之吡唑混合物 |
| WO2013126283A1 (en) | 2012-02-20 | 2013-08-29 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| JP6185056B2 (ja) * | 2012-06-22 | 2017-08-23 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 殺菌・殺カビ性４−メチルアニリノピラゾール |
| WO2017156493A1 (en) | 2016-03-11 | 2017-09-14 | Denali Therapeutics Inc. | Compounds, compositions, and methods |
| US20140235689A1 (en) * | 2013-02-20 | 2014-08-21 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| EP3010908A1 (en) | 2013-02-20 | 2016-04-27 | E. I. du Pont de Nemours and Company | Fungicidal pyrazoles |
| US20140288074A1 (en) * | 2013-03-22 | 2014-09-25 | E I Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI652012B (zh) * | 2013-05-20 | 2019-03-01 | 杜邦股份有限公司 | 殺真菌吡唑的固態形式 |
| WO2015026646A1 (en) | 2013-08-20 | 2015-02-26 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI652014B (zh) * | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| CN106458925A (zh) | 2014-05-06 | 2017-02-22 | 杜邦公司 | 杀真菌吡唑类 |
| JP2017522334A (ja) | 2014-07-24 | 2017-08-10 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺真菌性ピラゾール誘導体 |
| WO2016026830A1 (en) * | 2014-08-21 | 2016-02-25 | Bayer Cropscience Aktiengesellschaft | Novel fungicidal pyrazole derivatives |
| EP3271336A1 (en) | 2015-03-19 | 2018-01-24 | E. I. du Pont de Nemours and Company | Fungicidal pyrazoles |
| AU2016255724B2 (en) * | 2015-04-29 | 2020-05-14 | The State of Israel, Ministry of Agriculture and Rural Development Agricultural Research Organization (ARO) (Volcani Center) | Anti-phytopathogenic compositions |
| MX2017015261A (es) * | 2015-06-01 | 2018-02-19 | Ishihara Sangyo Kaisha | Composicion fungicida y procedimiento de control de enfermedades de las plantas. |
| US11214565B2 (en) | 2015-11-20 | 2022-01-04 | Denali Therapeutics Inc. | Compound, compositions, and methods |
| PT3472153T (pt) | 2016-06-16 | 2021-12-31 | Denali Therapeutics Inc | Pirimidin-2-ilamino-1h-pirazóis como inibidores de lrrk2 para uso no tratamento de distúrbios neurodegenerativos |
| WO2018052838A1 (en) | 2016-09-16 | 2018-03-22 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| CN107286097B (zh) | 2017-07-13 | 2019-06-25 | 青岛清原化合物有限公司 | 双唑草酮c晶型及其制备方法和用途 |
| EP3904350B1 (en) | 2018-04-12 | 2023-08-23 | Bayer Aktiengesellschaft | N-(cyclopropylmethyl)-5-(methylsulfonyl)-n-{1-[1-(pyrimidin-2-yl)-1h-1,2,4-triazol-5-yl]ethyl}benzamide derivatives and the corresponding pyridine-carboxamide derivatives as pesticides |
| TWI819078B (zh) * | 2018-09-06 | 2023-10-21 | 美商富曼西公司 | 殺真菌之經硝苯胺基取代之吡唑 |
| KR20210061364A (ko) * | 2018-09-14 | 2021-05-27 | 에프엠씨 코포레이션 | 살진균 할로메틸 케톤 및 수화물 |
| TW202200012A (zh) | 2020-03-11 | 2022-01-01 | 美商富曼西公司 | 殺真菌劑混合物 |
| CN113549053B (zh) * | 2020-04-23 | 2022-09-13 | 沈阳中化农药化工研发有限公司 | 一种吡唑喹（唑）啉醚类化合物及其应用 |
| US20240324596A1 (en) * | 2023-03-28 | 2024-10-03 | Fmc Corporation | Substituted tolyl fungicides |
Family Cites Families (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| NL7812293A (nl) | 1977-12-23 | 1979-06-26 | Montedison Spa | Fosforzuur en thiofosforzuuresters van 5(3)-hydroxypyrazolen met insecticide werking. |
| GB2054555A (en) * | 1979-07-27 | 1981-02-18 | Abbott Lab | Pyrazolyl amino imidazolines |
| GB2076801A (en) * | 1980-04-14 | 1981-12-09 | Erba Farmitalia | alpha , beta -Disubstituted Acrylamido Cephalosporins |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| JPH01319478A (ja) * | 1988-06-20 | 1989-12-25 | Mitsui Toatsu Chem Inc | 免疫調節作用を有する化合物 |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| DK0415688T3 (da) | 1989-08-30 | 1999-08-23 | Aeci Ltd | Fremgangsmåde til fremstilling af et doseringssystem samt fremgangsmåde til behandling af en genstand eller et locus |
| PL167613B1 (pl) | 1990-03-12 | 1995-09-30 | Du Pont | Granulowana kompozycja rozpuszczalna lub dyspergowalna w wodzie PL |
| US5189040A (en) * | 1990-05-28 | 1993-02-23 | Sumitomo Chemical Company, Limited | Pyrazole derivatives, method for producing the same and agricultural and/or horticultural fungicides containing the same as active ingredient |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| FR2676057B1 (fr) * | 1991-05-02 | 1995-03-03 | Therapeutique Moder Lab | Derives de 1,2-dithiole-3-thione, procede de preparation de ces derives, ainsi que l'utilisation de ces derives comme intermediaires de synthese ou comme medicaments. |
| FR2682379B1 (fr) | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
| WO1993019054A1 (en) * | 1992-03-26 | 1993-09-30 | Dowelanco | N-heterocyclic nitro anilines as fungicides |
| JPH0665237A (ja) * | 1992-05-07 | 1994-03-08 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| US5747497A (en) | 1993-05-12 | 1998-05-05 | E. I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| JPH0816059B2 (ja) * | 1993-05-21 | 1996-02-21 | 三井東圧化学株式会社 | 免疫調節剤 |
| DE4405207A1 (de) | 1994-02-18 | 1995-08-24 | Bayer Ag | N-Pyrazolylaniline und N-Pyrazolylaminopyridine |
| JPH08208620A (ja) | 1995-02-03 | 1996-08-13 | Takeda Chem Ind Ltd | アミノピラゾール誘導体、その製造法および用途 |
| JP4010563B2 (ja) | 1995-07-05 | 2007-11-21 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 殺菌・殺カビ性のピリミジノン類 |
| JPH09208620A (ja) | 1996-02-02 | 1997-08-12 | Sumitomo Bakelite Co Ltd | 硬化性エラストマー及びその製造方法 |
| CN1213373A (zh) | 1996-03-11 | 1999-04-07 | 诺瓦提斯公司 | 农药用嘧啶－4－酮衍生物 |
| CA2288787A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | Pyrazole derivatives as p38 kinase inhibitors |
| GB9719411D0 (en) | 1997-09-12 | 1997-11-12 | Ciba Geigy Ag | New Pesticides |
| JP2000095778A (ja) * | 1998-09-28 | 2000-04-04 | Ube Ind Ltd | ピラゾール誘導体、その製造法及び農園芸用の殺菌剤 |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| AR042067A1 (es) | 2002-11-27 | 2005-06-08 | Bayer Pharmaceuticals Corp | Derivados de anilinopirazol utiles en el tratamiento de la diabetes |
| GB0315657D0 (en) * | 2003-07-03 | 2003-08-13 | Astex Technology Ltd | Pharmaceutical compounds |
| US7517998B2 (en) | 2004-06-01 | 2009-04-14 | Boehringer Ingelheim International Gmbh | Non nucleoside reverse transcriptase inhibitors |
| CA2620425A1 (en) | 2005-08-31 | 2007-03-08 | Bayer Healthcare Llc | Anilinopyrazole derivatives useful for the treatment of diabetes |
| CA2652859A1 (en) | 2006-06-21 | 2007-12-27 | E.I. Du Pont De Nemours And Company | Pyrazinones as cellular proliferation inhibitors |
| EP2128138A1 (en) * | 2007-01-29 | 2009-12-02 | Takeda Pharmaceutical Company Limited | Pyrazole compound |
| PE20091953A1 (es) * | 2008-05-08 | 2010-01-09 | Du Pont | Azoles sustituidos como fungicidas |
| AR075713A1 (es) * | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| WO2011051958A1 (en) | 2009-10-30 | 2011-05-05 | E.I. Du Pont De Nemours And Company | Fungicidal pyrazolones |
| TW201117722A (en) | 2009-11-04 | 2011-06-01 | Du Pont | Fungicidal mixtures |
| WO2012023143A1 (en) | 2010-08-19 | 2012-02-23 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| TWI504350B (zh) | 2010-09-01 | 2015-10-21 | Du Pont | 殺真菌吡唑及其混合物 |
| TW201245155A (en) | 2010-09-01 | 2012-11-16 | Du Pont | Fungicidal pyrazoles |
| KR20130099268A (ko) | 2010-09-29 | 2013-09-05 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 살진균제 이미다졸 |
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