KR20130139892A - 살진균제 피라졸 - Google Patents

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Publication number

KR20130139892A

KR20130139892A KR20137008060A KR20137008060A KR20130139892A KR 20130139892 A KR20130139892 A KR 20130139892A KR 20137008060 A KR20137008060 A KR 20137008060A KR 20137008060 A KR20137008060 A KR 20137008060A KR 20130139892 A KR20130139892 A KR 20130139892A

Authority

KR

South Korea

Prior art keywords

compound

methyl

chloro

alkyl

pyrazole

Prior art date

2010-09-01

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.)

Withdrawn

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• 230000000855 fungicidal effect Effects 0.000 title claims description 119
• 150000003217 pyrazoles Chemical class 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 685
• 238000000034 method Methods 0.000 claims abstract description 60
• 150000003839 salts Chemical class 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 239000000417 fungicide Substances 0.000 claims description 257
• -1 cyanomethyl Chemical group 0.000 claims description 221
• 125000001424 substituent group Chemical group 0.000 claims description 151
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 91
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
• 229910052736 halogen Inorganic materials 0.000 claims description 73
• 229910052799 carbon Inorganic materials 0.000 claims description 70
• 150000002367 halogens Chemical class 0.000 claims description 70
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 125000004970 halomethyl group Chemical group 0.000 claims description 50
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 46
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 44
• 239000007787 solid Substances 0.000 claims description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims description 41
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 37
• 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 description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 229910052794 bromium Inorganic materials 0.000 claims description 29
• 150000001721 carbon Chemical group 0.000 claims description 29
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
• 229910052801 chlorine Inorganic materials 0.000 claims description 29
• 239000003085 diluting agent Substances 0.000 claims description 29
• 239000007788 liquid Substances 0.000 claims description 29
• 125000004414 alkyl thio group Chemical group 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 26
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
• 239000004094 surface-active agent Substances 0.000 claims description 23
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 18
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 18
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 18
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
• 125000001188 haloalkyl group Chemical group 0.000 claims description 15
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 13
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 12
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 12
• 125000002883 imidazolyl group Chemical group 0.000 claims description 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• 229910052708 sodium Inorganic materials 0.000 claims description 12
• 229910052700 potassium Inorganic materials 0.000 claims description 10
• 125000004434 sulfur atom Chemical group 0.000 claims description 9
• 244000000004 fungal plant pathogen Species 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
• 229910052744 lithium Inorganic materials 0.000 claims description 5
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 4
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• NQKFHVHGGAYYQI-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-[5-(2,6-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2Cl)Cl)=C1C(O)C1=CC=C(F)C=C1Br NQKFHVHGGAYYQI-UHFFFAOYSA-N 0.000 claims description 2
• IWLOCQHLFVNIRG-UHFFFAOYSA-N (2-bromo-4-fluorophenyl)-[5-(6-chloro-6-fluorocyclohexa-2,4-dien-1-yl)-1,3-dimethylpyrazol-4-yl]methanol Chemical compound BrC1=C(C=CC(=C1)F)C(O)C=1C(=NN(C=1C1C(C=CC=C1)(F)Cl)C)C IWLOCQHLFVNIRG-UHFFFAOYSA-N 0.000 claims description 2
• WCWOREXCTPWPDK-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)-[1,3-dimethyl-5-(2,4,6-trifluorophenyl)pyrazol-4-yl]methanol Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2F)F)=C1C(O)C1=CC=C(F)C=C1Cl WCWOREXCTPWPDK-UHFFFAOYSA-N 0.000 claims description 2
• BSLPGLKTSMHAEL-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)-[5-(2,6-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2Cl)Cl)=C1C(O)C1=CC=C(F)C=C1Cl BSLPGLKTSMHAEL-UHFFFAOYSA-N 0.000 claims description 2
• DEGPSPWKRQMMSZ-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)-[5-(2,6-difluorophenyl)-3-methoxy-1-methylpyrazol-4-yl]methanol Chemical compound COC1=NN(C)C(C=2C(=CC=CC=2F)F)=C1C(O)C1=CC=C(F)C=C1Cl DEGPSPWKRQMMSZ-UHFFFAOYSA-N 0.000 claims description 2
• LVWHXHJZTCVJOY-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)-[5-(2-chloro-6-fluorophenyl)-1,3-dimethylpyrazol-4-yl]methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=CC=C(F)C=C1Cl LVWHXHJZTCVJOY-UHFFFAOYSA-N 0.000 claims description 2
• LDEZHHORWWOOEV-UHFFFAOYSA-N (2-chloro-4-fluorophenyl)-[5-(2-chloro-6-fluorophenyl)-3-methoxy-1-methylpyrazol-4-yl]methanol Chemical compound COC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=CC=C(F)C=C1Cl LDEZHHORWWOOEV-UHFFFAOYSA-N 0.000 claims description 2
• VOBXXUKYLTWDDM-UHFFFAOYSA-N (2-chloro-4-methoxyphenyl)-[5-(2,6-difluorophenyl)-3-methoxy-1-methylpyrazol-4-yl]methanol Chemical compound COC1=NN(C)C(C=2C(=CC=CC=2F)F)=C1C(O)C1=CC=C(OC)C=C1Cl VOBXXUKYLTWDDM-UHFFFAOYSA-N 0.000 claims description 2
• AWACCWQDUDMTJE-UHFFFAOYSA-N 1-[2-[4-(2,4-dichlorobenzoyl)-2,5-dimethylpyrazol-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1C(N(N=C1C)C)=C1C(=O)C1=CC=C(Cl)C=C1Cl AWACCWQDUDMTJE-UHFFFAOYSA-N 0.000 claims description 2
• VAGLJWYKXJYGHQ-UHFFFAOYSA-N 3-chloro-4-[4-(2-chloro-4-fluorophenoxy)-2,5-dimethylpyrazol-3-yl]benzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(=CC=2)C#N)Cl)=C1OC1=CC=C(F)C=C1Cl VAGLJWYKXJYGHQ-UHFFFAOYSA-N 0.000 claims description 2
• VPTVABWVTXURCW-UHFFFAOYSA-N 3-chloro-4-[5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]oxybenzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1OC1=CC=C(C#N)C=C1Cl VPTVABWVTXURCW-UHFFFAOYSA-N 0.000 claims description 2
• YBCRYNSCGIUVLE-UHFFFAOYSA-N 4-(2-chloro-4-fluorobenzoyl)-5-(2,4-difluorophenyl)-1-methylpyrazole-3-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C=1N(C)N=C(C#N)C=1C(=O)C1=CC=C(F)C=C1Cl YBCRYNSCGIUVLE-UHFFFAOYSA-N 0.000 claims description 2
• HZMFFXSDUMADLO-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenoxy)-5-(2-chloro-4-methoxyphenyl)-1,3-dimethylpyrazole Chemical compound ClC1=CC(OC)=CC=C1C(N(N=C1C)C)=C1OC1=CC=C(F)C=C1Cl HZMFFXSDUMADLO-UHFFFAOYSA-N 0.000 claims description 2
• QHTQZOMSCLPRLF-UHFFFAOYSA-N 4-[4-[(2,4-difluorophenyl)-hydroxymethyl]-2,5-dimethylpyrazol-3-yl]-3,5-difluorobenzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(=CC=2F)C#N)F)=C1C(O)C1=CC=C(F)C=C1F QHTQZOMSCLPRLF-UHFFFAOYSA-N 0.000 claims description 2
• UTFCFZSOUVJAAZ-UHFFFAOYSA-N 4-[[5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]amino]-3,5-difluorobenzonitrile Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=C(F)C=C(C#N)C=C1F UTFCFZSOUVJAAZ-UHFFFAOYSA-N 0.000 claims description 2
• RPQMAAAKQQBETA-UHFFFAOYSA-N 5-(2-chloro-4-fluorophenyl)-n-(2,4-dichlorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=CC=C(Cl)C=C1Cl RPQMAAAKQQBETA-UHFFFAOYSA-N 0.000 claims description 2
• NQOGYNADXHMSJG-UHFFFAOYSA-N 5-(2-chloro-4-fluorophenyl)-n-(4-chloro-2-fluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=CC=C(Cl)C=C1F NQOGYNADXHMSJG-UHFFFAOYSA-N 0.000 claims description 2
• KAICHMJALBRCMR-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)-4-(2,4-difluorophenoxy)-1,3-dimethylpyrazole Chemical compound ClC1=CC(OC)=CC=C1C(N(N=C1C)C)=C1OC1=CC=C(F)C=C1F KAICHMJALBRCMR-UHFFFAOYSA-N 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• PEMFTUFHCGCZIV-UHFFFAOYSA-N [3-bromo-5-(2,6-difluorophenyl)-1-methylpyrazol-4-yl]-(2-chloro-4-fluorophenyl)methanol Chemical compound FC=1C=CC=C(F)C=1C=1N(C)N=C(Br)C=1C(O)C1=CC=C(F)C=C1Cl PEMFTUFHCGCZIV-UHFFFAOYSA-N 0.000 claims description 2
• SZNHBKNMTMCTIE-UHFFFAOYSA-N [3-bromo-5-(2-chloro-4-fluorophenyl)-1-methylpyrazol-4-yl]-(2,4-difluorophenyl)methanol Chemical compound C=1C=C(F)C=C(Cl)C=1C=1N(C)N=C(Br)C=1C(O)C1=CC=C(F)C=C1F SZNHBKNMTMCTIE-UHFFFAOYSA-N 0.000 claims description 2
• HEYOHXJWBDVQAP-UHFFFAOYSA-N [3-chloro-5-(2,6-difluorophenyl)-1-methylpyrazol-4-yl]-(2-chloro-4-fluorophenyl)methanol Chemical compound FC=1C=CC=C(F)C=1C=1N(C)N=C(Cl)C=1C(O)C1=CC=C(F)C=C1Cl HEYOHXJWBDVQAP-UHFFFAOYSA-N 0.000 claims description 2
• SJHGDMKKYPXPKX-UHFFFAOYSA-N [3-chloro-5-(2,6-difluorophenyl)-1-methylpyrazol-4-yl]-(2-chloro-4-methoxyphenyl)methanol Chemical compound ClC1=CC(OC)=CC=C1C(O)C1=C(C=2C(=CC=CC=2F)F)N(C)N=C1Cl SJHGDMKKYPXPKX-UHFFFAOYSA-N 0.000 claims description 2
• YPWBXKWDBJJXHG-UHFFFAOYSA-N [3-chloro-5-(2,6-difluorophenyl)-1-methylpyrazol-4-yl]-(2-fluoro-4-methoxyphenyl)methanol Chemical compound FC1=CC(OC)=CC=C1C(O)C1=C(C=2C(=CC=CC=2F)F)N(C)N=C1Cl YPWBXKWDBJJXHG-UHFFFAOYSA-N 0.000 claims description 2
• UCJPRVMPGXIWKT-UHFFFAOYSA-N [3-chloro-5-(2,6-difluorophenyl)-1-methylpyrazol-4-yl]-(4-methoxy-2-methylphenyl)methanol Chemical compound CC1=CC(OC)=CC=C1C(O)C1=C(C=2C(=CC=CC=2F)F)N(C)N=C1Cl UCJPRVMPGXIWKT-UHFFFAOYSA-N 0.000 claims description 2
• GWDNKAWDDPXGKQ-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC(Cl)=CC=2)Cl)=C1C(O)C1=CC=C(F)C=C1F GWDNKAWDDPXGKQ-UHFFFAOYSA-N 0.000 claims description 2
• JLUJLAXFYSMHCJ-UHFFFAOYSA-N [5-(2,4-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanone Chemical compound CC1=NN(C)C(C=2C(=CC(Cl)=CC=2)Cl)=C1C(=O)C1=CC=C(F)C=C1F JLUJLAXFYSMHCJ-UHFFFAOYSA-N 0.000 claims description 2
• IKEUFJWLZKKKDW-UHFFFAOYSA-N [5-(2,6-dichlorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2Cl)Cl)=C1C(O)C1=CC=C(F)C=C1F IKEUFJWLZKKKDW-UHFFFAOYSA-N 0.000 claims description 2
• OBSZQEGJMHQZRS-UHFFFAOYSA-N [5-(2,6-difluorophenyl)-3-methoxy-1-methylpyrazol-4-yl]-(4-fluoro-2-methylphenyl)methanol Chemical compound COC1=NN(C)C(C=2C(=CC=CC=2F)F)=C1C(O)C1=CC=C(F)C=C1C OBSZQEGJMHQZRS-UHFFFAOYSA-N 0.000 claims description 2
• JJKFOFRMRHCJME-UHFFFAOYSA-N [5-(2,6-difluorophenyl)-3-methoxy-1-methylpyrazol-4-yl]-(4-methoxy-2-methylphenyl)methanol Chemical compound COC1=NN(C)C(C=2C(=CC=CC=2F)F)=C1C(O)C1=CC=C(OC)C=C1C JJKFOFRMRHCJME-UHFFFAOYSA-N 0.000 claims description 2
• PGKOFICYYSPEQW-UHFFFAOYSA-N [5-(2-bromo-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4,6-trifluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Br)=C1C(O)C1=C(F)C=C(F)C=C1F PGKOFICYYSPEQW-UHFFFAOYSA-N 0.000 claims description 2
• CYLDPYMXJSDNCB-UHFFFAOYSA-N [5-(2-bromophenyl)-1,3-dimethylpyrazol-4-yl]-(2-chloro-4-fluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2)Br)=C1C(O)C1=CC=C(F)C=C1Cl CYLDPYMXJSDNCB-UHFFFAOYSA-N 0.000 claims description 2
• AIZWQAAGWOKNHY-UHFFFAOYSA-N [5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4,6-trifluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1C(O)C1=C(F)C=C(F)C=C1F AIZWQAAGWOKNHY-UHFFFAOYSA-N 0.000 claims description 2
• BEGBWJDIIRBATB-UHFFFAOYSA-N [5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1C(O)C1=CC=C(F)C=C1F BEGBWJDIIRBATB-UHFFFAOYSA-N 0.000 claims description 2
• GWBVMIQQZAXCKD-UHFFFAOYSA-N [5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-yl]methanol Chemical compound ClC1=C(C=CC(=C1)F)C1=C(C(=NN1C)C)CO GWBVMIQQZAXCKD-UHFFFAOYSA-N 0.000 claims description 2
• WQKBDJXLTDZTIP-UHFFFAOYSA-N [5-(2-chloro-6-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-dichlorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=CC=C(Cl)C=C1Cl WQKBDJXLTDZTIP-UHFFFAOYSA-N 0.000 claims description 2
• AUZJCBUITKVSHI-UHFFFAOYSA-N [5-(2-chloro-6-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,4-difluorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=CC=C(F)C=C1F AUZJCBUITKVSHI-UHFFFAOYSA-N 0.000 claims description 2
• INJNUIXFZLBSJM-UHFFFAOYSA-N [5-(2-chloro-6-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2,6-dichlorophenyl)methanol Chemical compound CC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=C(Cl)C=CC=C1Cl INJNUIXFZLBSJM-UHFFFAOYSA-N 0.000 claims description 2
• XXBWXUAKVJECKN-UHFFFAOYSA-N [5-(2-chloro-6-fluorophenyl)-1,3-dimethylpyrazol-4-yl]-(2-chloro-4-methoxyphenyl)methanol Chemical compound ClC1=CC(OC)=CC=C1C(O)C1=C(C=2C(=CC=CC=2F)Cl)N(C)N=C1C XXBWXUAKVJECKN-UHFFFAOYSA-N 0.000 claims description 2
• FWATYENPNQPXCE-UHFFFAOYSA-N [5-(2-chloro-6-fluorophenyl)-3-methoxy-1-methylpyrazol-4-yl]-(2-chloro-4-methoxyphenyl)methanol Chemical compound COC1=NN(C)C(C=2C(=CC=CC=2F)Cl)=C1C(O)C1=CC=C(OC)C=C1Cl FWATYENPNQPXCE-UHFFFAOYSA-N 0.000 claims description 2
• ZRQQNZXCQKQFOX-UHFFFAOYSA-N n,5-bis(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=CC=C(F)C=C1Cl ZRQQNZXCQKQFOX-UHFFFAOYSA-N 0.000 claims description 2
• YWPBOTMILQCGPL-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-5-(2,4-difluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)F)=C1NC1=CC=C(Cl)C=C1Cl YWPBOTMILQCGPL-UHFFFAOYSA-N 0.000 claims description 2
• FSSNPLPILKGTLI-UHFFFAOYSA-N n-(2-bromo-4-fluorophenyl)-5-(2-chloro-4-fluorophenyl)-1,3-dimethylpyrazol-4-amine Chemical compound CC1=NN(C)C(C=2C(=CC(F)=CC=2)Cl)=C1NC1=CC=C(F)C=C1Br FSSNPLPILKGTLI-UHFFFAOYSA-N 0.000 claims description 2
• 239000000203 mixture Substances 0.000 abstract description 138
• 244000053095 fungal pathogen Species 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
• 230000009471 action Effects 0.000 description 69
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
• 238000006243 chemical reaction Methods 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 43
• 241000196324 Embryophyta Species 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• 239000000460 chlorine Substances 0.000 description 38
• 230000002829 reductive effect Effects 0.000 description 38
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 239000000463 material Substances 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• 230000012010 growth Effects 0.000 description 27
• 238000012360 testing method Methods 0.000 description 27
• 241000233866 Fungi Species 0.000 description 26
• 239000003480 eluent Substances 0.000 description 26
• 235000019441 ethanol Nutrition 0.000 description 26
• 238000009472 formulation Methods 0.000 description 26
• 229920006395 saturated elastomer Polymers 0.000 description 25
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