HRP20160111T1 - Fungicidni pirazoli - Google Patents
Fungicidni pirazoli Download PDFInfo
- Publication number
- HRP20160111T1 HRP20160111T1 HRP20160111T HRP20160111T HRP20160111T1 HR P20160111 T1 HRP20160111 T1 HR P20160111T1 HR P20160111 T HRP20160111 T HR P20160111T HR P20160111 T HRP20160111 T HR P20160111T HR P20160111 T1 HRP20160111 T1 HR P20160111T1
- Authority
- HR
- Croatia
- Prior art keywords
- dimethyl
- pyrazol
- oxy
- dichloro
- alkyl
- Prior art date
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- 230000000855 fungicidal effect Effects 0.000 title claims 4
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 claims 35
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 22
- -1 cyano, cyanomethyl Chemical group 0.000 claims 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 229910052794 bromium Inorganic materials 0.000 claims 9
- 229910052801 chlorine Inorganic materials 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 6
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- JESOYYBATIWBLO-QMMMGPOBSA-N (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)pyrazol-3-yl]oxyphenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(OC=2N(N=C(C)C=2C=2ON=C(C)N=2)C)=C1Cl JESOYYBATIWBLO-QMMMGPOBSA-N 0.000 claims 4
- ZROMNHFZXMIESR-QMMMGPOBSA-N (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)pyrazol-3-yl]oxyphenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(OC=2N(N=C(C)C=2C=2SC(C)=NN=2)C)=C1Cl ZROMNHFZXMIESR-QMMMGPOBSA-N 0.000 claims 4
- FZMUSKDNJIPFJQ-JTQLQIEISA-N (2s)-2-[2,4-dichloro-5-[4-[5-(2-hydroxypropan-2-yl)-1,2-oxazol-3-yl]-2,5-dimethylpyrazol-3-yl]oxyphenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(OC=2N(N=C(C)C=2C2=NOC(=C2)C(C)(C)O)C)=C1Cl FZMUSKDNJIPFJQ-JTQLQIEISA-N 0.000 claims 4
- XBSGGCDQLKPFIU-VIFPVBQESA-N (2s)-2-[2,4-dichloro-5-[4-[5-(hydroxymethyl)-1,2-oxazol-3-yl]-2,5-dimethylpyrazol-3-yl]oxyphenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(OC=2N(N=C(C)C=2C2=NOC(CO)=C2)C)=C1Cl XBSGGCDQLKPFIU-VIFPVBQESA-N 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- OLXMZNUBLXFWJS-UHFFFAOYSA-N 2,4-dichloro-5-[2,5-dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)pyrazol-3-yl]oxyphenol Chemical compound CC1=NOC(C2=C(N(C)N=C2C)OC=2C(=CC(Cl)=C(O)C=2)Cl)=N1 OLXMZNUBLXFWJS-UHFFFAOYSA-N 0.000 claims 4
- VNVPULLWAMXHLM-UHFFFAOYSA-N 2,4-dichloro-5-[2,5-dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)pyrazol-3-yl]oxyphenol Chemical compound S1C(C)=NN=C1C1=C(OC=2C(=CC(Cl)=C(O)C=2)Cl)N(C)N=C1C VNVPULLWAMXHLM-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 101150020251 NR13 gene Proteins 0.000 claims 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000004995 haloalkylthio group Chemical group 0.000 claims 4
- WSNWHOHZIPGREZ-JTQLQIEISA-N methyl (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(1,2-oxazol-3-yl)pyrazol-3-yl]oxyphenoxy]propanoate Chemical compound C1=C(Cl)C(O[C@@H](C)C(=O)OC)=CC(OC=2N(N=C(C)C=2C2=NOC=C2)C)=C1Cl WSNWHOHZIPGREZ-JTQLQIEISA-N 0.000 claims 4
- XTBBLYYQEMMPHL-VIFPVBQESA-N methyl (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)pyrazol-3-yl]oxyphenoxy]propanoate Chemical compound C1=C(Cl)C(O[C@@H](C)C(=O)OC)=CC(OC=2N(N=C(C)C=2C=2ON=C(C)N=2)C)=C1Cl XTBBLYYQEMMPHL-VIFPVBQESA-N 0.000 claims 4
- NRDAMHZGFQSWEF-VIFPVBQESA-N methyl (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(5-methyl-1,3,4-thiadiazol-2-yl)pyrazol-3-yl]oxyphenoxy]propanoate Chemical compound C1=C(Cl)C(O[C@@H](C)C(=O)OC)=CC(OC=2N(N=C(C)C=2C=2SC(C)=NN=2)C)=C1Cl NRDAMHZGFQSWEF-VIFPVBQESA-N 0.000 claims 4
- BAXSNSGCDONGMU-NSHDSACASA-N methyl (2s)-2-[2,4-dichloro-5-[4-[5-(2-hydroxypropan-2-yl)-1,2-oxazol-3-yl]-2,5-dimethylpyrazol-3-yl]oxyphenoxy]propanoate Chemical compound C1=C(Cl)C(O[C@@H](C)C(=O)OC)=CC(OC=2N(N=C(C)C=2C2=NOC(=C2)C(C)(C)O)C)=C1Cl BAXSNSGCDONGMU-NSHDSACASA-N 0.000 claims 4
- QNGAXNMUIBVPLB-JTQLQIEISA-N methyl (2s)-2-[2,4-dichloro-5-[4-[5-(hydroxymethyl)-1,2-oxazol-3-yl]-2,5-dimethylpyrazol-3-yl]oxyphenoxy]propanoate Chemical compound C1=C(Cl)C(O[C@@H](C)C(=O)OC)=CC(OC=2N(N=C(C)C=2C2=NOC(CO)=C2)C)=C1Cl QNGAXNMUIBVPLB-JTQLQIEISA-N 0.000 claims 4
- RHVURCUUFRFSDT-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-2,5-dimethyl-4-phenylpyrazol-3-amine Chemical compound C=1C=CC=CC=1C=1C(C)=NN(C)C=1NC1=NCCN1 RHVURCUUFRFSDT-UHFFFAOYSA-N 0.000 claims 4
- PTSWCPFXUBDMNF-VIFPVBQESA-N (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(1,2-oxazol-3-yl)pyrazol-3-yl]oxyphenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(OC=2N(N=C(C)C=2C2=NOC=C2)C)=C1Cl PTSWCPFXUBDMNF-VIFPVBQESA-N 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 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
- 229910006067 SO3−M Inorganic materials 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 3
- LLGJTFCZKIOWAA-NSHDSACASA-N methyl (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(5-methyl-1,2-oxazol-3-yl)pyrazol-3-yl]oxyphenoxy]propanoate Chemical compound C1=C(Cl)C(O[C@@H](C)C(=O)OC)=CC(OC=2N(N=C(C)C=2C2=NOC(C)=C2)C)=C1Cl LLGJTFCZKIOWAA-NSHDSACASA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 235000019260 propionic acid Nutrition 0.000 claims 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- OTBLKQNPJIGLOC-JTQLQIEISA-N (2s)-2-[2,4-dichloro-5-[2,5-dimethyl-4-(5-methyl-1,2-oxazol-3-yl)pyrazol-3-yl]oxyphenoxy]propanoic acid Chemical compound C1=C(Cl)C(O[C@@H](C)C(O)=O)=CC(OC=2N(N=C(C)C=2C2=NOC(C)=C2)C)=C1Cl OTBLKQNPJIGLOC-JTQLQIEISA-N 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio 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
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-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
- ICPUBUJYUQMSGY-UHFFFAOYSA-N 4-(2-bromo-4-fluorophenyl)-n-(2-chloro-4,6-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(F)C=C1Cl ICPUBUJYUQMSGY-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
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 239000005747 Chlorothalonil Substances 0.000 claims 1
- 239000005868 Metconazole Substances 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 239000005825 Prothioconazole Substances 0.000 claims 1
- 241000607479 Yersinia pestis Species 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims 1
- 125000005724 cycloalkenylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 244000000004 fungal plant pathogen Species 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Claims (18)
1. Spoj izabran od formule 1, njegovih N-oksida i soli,
[image]
u kojem
Q1 je fenil prsten ili naftalenil sustav prstena, pri čemu je svaki prsten ili sustav prstena izborno supstituiran sa do 5 supstituenata nezavisno izabranih od R3; ili 5- do 6-člani potpuno nezasićeni heterociklični prsten ili 8- do 10-člani heteroaromatični biciklični sustav prstena, pri čemu svaki prsten ili sustav prstena sadrži članove prstena izabrane od atoma ugljika i do 4 heteroatoma nezavisno izabrana od do 2 O, do 2 S i do 4 N atoma, pri čemu su do 3 ugljikova člana prstena nezavisno izabrana od C(=O) i C(=S), i članovi prstena koji su atomi sumpora su nezavisno izabrani od S(=O)u(=NR14)v, pri čemu je svaki prsten ili sustav prstena izborno supstituiran sa do 5 supstituenata nezavisno izabranih od R3 na članovima prstena koji su atomi ugljika i izabrani od cijano, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C3-C6 cikloalkil, C1-C6 alkoksi, C2-C6 alkoksialkil, C2-C6 alkilkarbonil, C2-C6 alkoksikarbonil, C2-C6 alkilaminoalkil i C3-C6 dialkilaminoalkil na članovima prstena koji su atomi dušika;
Q2 je fenil prsten ili naftalenil sustav prstena, pri čemu je svaki prsten ili sustav prstena izborno supstituiran sa do 5 supstituenata nezavisno izabranih od R3; ili 5- do 6-člani zasićeni, djelomično nezasićen ili potpuno nezasićen heterociklični prsten ili 8- do 10-člani heteroaromatični biciklični sustav prstena, pri čemu svaki prsten ili sustav prstena sadrži članove prstena izabrane od atoma ugljika i do 4 heteroatoma nezavisno izabrana od do 2 O, do 2 S i do 4 N atoma, pri čemu su do 3 ugljikova člana prstena nezavisno izabrana od C(=O) i C(=S), i članovi prstena koji su atomi sumpora su nezavisno izabrani od S(=O)u(=NR14)v, pri čemu je svaki prsten ili sustav prstena izborno supstituiran sa do 5 supstituenata nezavisno izabranih od R3 na članovima prstena koji su atomi ugljika i izabrani od cijano, C1-C6 alkil, C2-C6 alkenil, C2-C6 alkinil, C3-C6 cikloalkil, C1-C6 alkoksi, C2-C6 alkoksialkil, C2-C6 alkilkarbonil, C2-C6 alkoksikarbonil, C2-C6 alkilaminoalkil i C3-C6 dialkilaminoalkil na članovima prstena koji su atomi dušika; ili C1-C12 alkil, C2-C12 alkenil, C2-C12 alkinil, C3-C12 cikloalkil ili C3-C12 cikloalkenil, svaki izborno supstituiran sa do 5 supstituenata nezavisno izabrana od R3;
X je O, S(O)m ili NR4;
R1 je H, halogen, C1-C6 alkil, C1-C6 haloalkil, C2-C4 alkenil, C2-C4 alkinil, C3-C7 cikloalkil, CO2R5, C(O)NR6R7, cijano, C1-C6 alkoksi, C1-C6 haloalkoksi ili C2-C5 alkoksialkil; ili
R1 je fenil izborno supstituiran sa do 3 R8; ili pet- ili šesto-člani aromatični heterociklus koji sadrži dušik izborno supstituiran sa do 3 supstituenta nezavisno izabrana od R9a na članovima prstena koji su atomi ugljika i R9b na članovima prstena koji su atomi dušika;
R1a je H; ili
R1a i R1 su povezani sa atomom ugljika za koji su vezani tako da formiraju ciklopropil prsten izborno supstituiran sa do 2 supstituenta nezavisno izabrana od halogena i metila;
R2 je CH3, CH2CH3, halogen, cijano, cijanometil, halo metil, hidroksimetil, metoksi ili metiltio; ili ciklopropil izborno supstituiran sa do 2 supstituenta nezavisno izabrana od halogena i metila;
svaki R3 je nezavisno izabran od halogena, cijano, amino, metilamino, dimetilamino, formilamino, C2-C3 alkilkarbonilamino, C1-C4 alkil, C1-C4 haloalkil, C1-C3 alkoksi, C1-C3 haloalkoksi, C1-C3 alkiltio, C1-C3 haloalkiltio, C1-C3 alkilsulfinil, C1-C3 haloalkilsulfinil, C1-C3 alkilsulfonil, C1-C3 haloalkilsulfonil, C1-C2 alkilsulfoniloksi, C1-C2 haloalkilsulfoniloksi, C3-C4 cikloalkil, C3-C7 cikloalkoksi, C4-C6 alkilcikloalkil, C4-C6 cikloalkilalkil, C3-C7 halocikloalkil, C2-C4 alkenil, C2-C4 alkinil, hidroksi, formil, C2-C3 alkilkarbonil, C2-C3 alkilkarboniloksi, -SF5, -SCN, C(=S)NR19R20 i -U-V-T;
R4 je H, formil, C2-C5 alkenil, C3-C5 alkinil, C3-C7 cikloalkil, -SO3-M+, -S(=O)tR10, -(C=W)R11, NH2 ili OR21; ili C1-C6 alkil ili C1-C6 haloalkil, svaki izborno supstituiran sa do 2 R12;
R5 je H, C1-C6 alkil ili C1-C6 haloalkil;
R6 i R7 su nezavisno izabrani od H, C1-C6 alkil, C1-C6 haloalkil, C3-C7 cikloalkil, C4-C8 cikloalkilalkil i C4-C8 alkilcikloalkil; ili
R6 i R7 su povezani sa atomom dušika za koji su vezani tako da formiraju četvoro- do sedmo-člani nearomatični heterociklični prsten koji sadrži članove prstena, pored atoma dušika koji povezuje prsten, izabrane od atoma ugljika i izborno do jedan član prstena izabran od O, S(O)n i NR13;
svaki R8, R9a i R9b je nezavisno izabran od halogena, C1-C2 alkil, C1-C2 haloalkil, C1-C2 alkoksi, C1-C2 haloalkoksi, cijano, nitro, SCH3, S(O)CH3 i S(O)2CH3;
R10 je C1-C6 alkil ili C1-C6 haloalkil;
R11 je C1-C6 alkil, C1-C6 alkoksi, C2-C7 alkoksialkil, C2-C7 alkilaminoalkil, C3-C8 dialkilaminoalkil, C1-C6 alkiltio ili C2-C7 alkiltioalkil;
svaki R12 je nezavisno C3-C7 cikloalkil, C1-C4 alkoksi, C1-C4 haloalkoksi, C1-C4 alkiltio, C1-C4 alkilsulfinil, C1-C4 alkilsulfonil ili cijano;
R13 je H, C1-C3 alkil ili C2-C3 haloalkil;
svaki R14 je nezavisno H, cijano, C1-C3 alkil ili C1-C3 haloalkil;
svaki R19 i R20 je nezavisno H ili CH3;
R21 je H, formil, C3-C7 cikloalkil, -SO3-M+ ili -(C=W)R11; ili C1-C6 alkil ili C1-C6 haloalkil, svaki izborno supstituiran sa do 2 R12;
svaki U je nezavisno O, S(=O)W, NR22 ili direktna veza;
svaki V je nezavisno C1-C6 alkilen, C2-C6 alkenilen, C3-C6 alkinilen, C3-C6 cikloalkilen ili C3-C6 cikloalkenilen, gdje su do 3 atoma ugljika nezavisno izabrana od C(=O), svaki izborno supstituiran sa do 5 supstituenata nezavisno izabrana od halogena, cijano, nitro, hidroksi, C1-C6 alkil, C1-C6 haloalkil, C1-C6 alkoksi i C1-C6 haloalkoksi;
svaki T je nezavisno cijano, NR23aR23b, OR24 ili S(=O)yR25;
svaki R22 je nezavisno H, C1-C6 alkil, C1-C6 haloalkil, C2-C6 alkilkarbonil, C2-C6 alkoksikarbonil, C2-C6 (alkiltio)karbonil, C2-C6 alkoksi(tiokarbonil), C4-C8 cikloalkilkarbonil, C4-C8 cikloalkoksikarbonil, C4-C8 (cikloalkiltio)karbonil ili C4-C8 cikloalkoksi(tiokarbonil);
svaki R23a i R23b je nezavisno H, C1-C6 alkil, C1-C6 haloalkil, C2-C6 alkenil, C3-C6 alkinil, C3-C6 cikloalkil, C3-C6 halocikloalkil, C2-C6 alkilkarbonil, C2-C6 alkoksikarbonil, C2-C6 (alkiltio)karbonil, C2-C6 alkoksi(tiokarbonil), C4-C8 cikloalkilkarbonil, C4-C8 cikloalkoksikarbonil, C4-C8 (cikloalkiltio)karbonil ili C4-C8 cikloalkoksi(tiokarbonil); ili
par R23a i R23b vezan za isti atom dušika su povezani sa atomom dušika tako da formiraju 3- do 6-člani heterociklični prsten, pri čemu je prsten izborno supstituiran sa do 5 supstituenata nezavisno izabrana od R26;
svaki R24 i R25 je nezavisno H, C1-C6 alkil, C1-C6 haloalkil, C2-C6 alkenil, C3-C6 alkinil, C3-C6 cikloalkil, C3-C6 halocikloalkil, C2-C6 alkilkarbonil, C2-C6 alkoksikarbonil, C2-C6 (alkiltio)karbonil, C2-C6 alkoksi(tiokarbonil), C4-C8 cikloalkilkarbonil, C4-C8 cikloalkoksikarbonil, C4-C8 (cikloalkiltio)karbonil ili C4-C8 cikloalkoksi(tiokarbonil);
svaki R26 je nezavisno halogen, C1-C6 alkil, C1-C6 haloalkil ili C1-C6 alkoksi;
W je O ili S;
M+ je kation;
m je 0, 1 ili 2;
n je 0, 1 ili 2;
t je 0, 1 ili 2;
svaki u i v su nezavisno 0, 1 ili 2 u svakom slučaju od S(=O)u(=NR14)v, uz uvjet da je zbroj u i v jednak 0, 1 ili 2;
svaki w je nezavisno 0, 1 ili 2; i
svaki y je nezavisno 0, 1 ili 2;
uz uvjet da:
kada je Q2 jednak fenil prsten supstituiran na najmanje jednim orto položajem sa supstituentom izabranim od -U-V-T, gdje U je direktna veza, V je C(=O) i T je NR23aR23b ili OR24, tada se X razlikuje od NR4;
i uz uvjet da se spoj formule 1 razlikuje od:
(a) 2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenola;
(b) 2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenola;
(c)
[image]
(d) 2-(1,3-dimetil-4-fenilpirazolil)amino-2-imidazolin HCl;
(e) metil (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionata;
(f) (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline;
(g) metil (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata;
(h) (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline;
(i) metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi}fenoksi)propionata;
(j) (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline;
(k) metil (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata;
(l) (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline;
(m) (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline;
(n) metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionata;
(o) (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; ili
(p) metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionata.
2. Spoj prema patentnom zahtjevu 1 u kojem:
Q1 je fenil, piridinil, pirimidinil, pirazinil ili piridazinil, svaki supstituiran sa od 1 do 4 supstituenta nezavisno izabrana od R3; pod uvjetom da kada se R3 supstituent nalazi na meta položaju, tada navedeni R3 supstituent je izabran od F, Cl, Br i cijano;
Q2 je fenil, piridinil, pirimidinil, pirazinil ili piridazinil, svaki supstituiran sa 1, 2 ili 3 supstituenta nezavisno izabrana od R3, pod uvjetom da kada se R3 supstituent nalazi na meta položaju, tada je navedeni R3 supstituent izabran od F, Cl, Br i cijano;
X je O ili NR4;
R1 je H, halogen, C1-C6 alkil, C1-C6 haloalkil, CO2R5, C(O)NR6R7, cijano, C1-C6 alkoksi, C1-C6 haloalkoksi ili C2-C5 alkoksialkil;
R1a je H;
R2 je CH3, CH2CH3, Cl ili Br;
svaki R3 je nezavisno izabran od halogena, cijano, amino, metilamino, dimetilamino, C1-C4 alkil, C1-C4 haloalkil, C1-C3 alkoksi, C1-C3 haloalkoksi C1-C3 alkiltio, C1-C3 haloalkiltio, C1-C3 alkilsulfinil, C1-C3 haloalkilsulfinil, C1-C3 alkilsulfonil, C1-C3 haloalkilsulfonil, C3-C4 cikloalkil, C(=S)NH2 i -U-V-T;
R4 je H, formil, C3-C7 cikloalkil ili -SR10; ili C1-C6 alkil ili C1-C6 haloalkil, svaki izborno supstituiran sa do 2 R12;
R5 je C1-C6 alkil;
R6 je H ili C1-C6 alkil;
R7 je H, C1-C6 alkil, C1-C6 haloalkil ili C4-C8 alkilcikloalkil; ili
R6 i R7 su povezani sa atomom dušika za koji su vezani tako da formiraju četvoro- do sedmo-člani nearomatični heterociklični prsten koji sadrži članove prstena, pored vežućeg atoma dušika, izabrane od atoma ugljika i do jedan član prstena izabran od O i NR13;
svaki R12 je nezavisno C3-C7 cikloalkil, C1-C4 alkoksi ili cijano; i
R13 je H ili CH3.
3. Spoj prema patentnom zahtjevu 2 u kojem
Q1 je fenil ili piridinil, svaki supstituiran sa 1, 2 ili 3 supstituenta nezavisno izabrana od R3;
Q2 je fenil ili piridinil, svaki supstituiran sa 1, 2 ili 3 supstituenta nezavisno izabrana od R3;
R1 je H, halogen ili C1-C6 alkil;
R2 je CH3, Cl ili Br;
svaki R3 je nezavisno izabran od halogena, cijano, C1-C4 alkil, C1-C4 haloalkil, C1-C3 alkoksi, C1-C3 haloalkoksi i -U-V-T;
R4 je H, formil, C3-C7 cikloalkil ili -SR10; ili C1-C6 alkil supstituiran sa jednim R12; R12 je ciklopropil, -OCH3 ili cijano;
svaki U je nezavisno O ili NH;
svaki V je nezavisno C2-C4 alkilen;
svaki T je nezavisno NR23aR23b ili OR24;
svaki R23a i R23b je nezavisno H, C1-C6 alkil ili C1-C6 haloalkil; i svaki R24 je nezavisno H, C1-C6 alkil ili C1-C6 haloalkil.
4. Spoj prema patentnom zahtjevu 3 u kojem
najmanje jedan od Q1 i Q2 je fenil supstituiran sa 2 ili 3 supstituenta nezavisno izabrana od R3;
R1 je H ili CH3;
R2 je CH3;
R4 je H;
svaki R3 je nezavisno izabran od halogena, cijano, C1-C3 alkil, C1-C3 haloalkil, C1-C3 alkoksi i C1-C3 haloalkoksi.
5. Spoj prema patentnom zahtjevu 4 u kojem
Q1 je fenil supstituiran na 2-, 4- i 6-položajima sa supstituentima nezavisno izabranim od R3; ili fenil supstituiran na 2- i 4-položajima sa supstituentima nezavisno izabranim od R3; ili fenil supstituiran na 2- i 6-položajima sa supstituentima nezavisno izabranim od R3;
Q2 je fenil supstituiran na 2-, 4- i 6-položajima sa supstituentima nezavisno izabranim od R3; ili fenil supstituiran na 2- i 4-položajima sa supstituentima nezavisno izabranim od R3; ili fenil supstituiran na 2- i 6-položajima sa supstituentima nezavisno izabranim od R3;
R1 je H; i
svaki R3 je nezavisno izabran od F, Cl, Br, cijano, C1-C2 alkil, C1-C2 haloalkil, C1-C2 alkoksi i C1-C2 haloalkoksi.
6. Spoj prema patentnom zahtjevu 5 u kojem
svaki R3 je nezavisno izabran od F, Cl, Br, cijano, metil, C1-C2 alkoksi i fluorometoksi.
7. Spoj prema patentnom zahtjevu 6 u kojem
X je O ili NH; i
svaki R3 je nezavisno izabran od F, Cl, Br, cijano i metoksi.
8. Spoj prema patentnom zahtjevu 1 u kojem
R1a je H;
Q1 i Q2 su nezavisno fenil, tienil, piridinil, piridazinil, pirazinil ili pirimidinil, svaki izborno supstituiran sa do 5 supstituenta nezavisno izabrana od R3;
X je O, S(O)m ili NR4;
R1 je H, halogen, C1-C6 alkil, C1-C6 haloalkil, C2-C4 alkenil, C2-C4 alkinil, C3-C7 cikloalkil, CO2R5, C(O)NR6R7, cijano, C1-C6 alkoksi, C1-C6 haloalkoksi ili C2-C5 alkoksialkil; ili
R1 je fenil izborno supstituiran sa do 3 R8; ili pet- ili šesto-člani aromatični heterociklus koji sadrži dušik izborno supstituiran sa do 3 supstituenta nezavisno izabrana od R9a na članovima prstena koji su atomi ugljika i R9b na članovima prstena koji su atomi dušika;
R2 je CH3, CH2CH3, ciklopropil ili halogen;
svaki R3 je nezavisno izabran od halogena, cijano, amino, metilamino, dimetilamino, C1-C4 alkil, C1-C4 haloalkil, C1-C3 alkoksi, C1-C3 haloalkoksi, C1-C3 alkiltio, C1-C3 haloalkiltio, C1-C3 alkilsulfinil, C1-C3 haloalkilsulfinil, C1-C3 alkilsulfonil, C1-C3 haloalkilsulfonil, C3-C4 cikloalkil, C3-C7 cikloalkoksi, C4-C6 alkilcikloalkil, C4-C6 cikloalkilalkil, C3-C7 halocikloalkil, C2-C4 alkenil i C2-C4 alkinil;
R4 je H, formil, C3-C7 cikloalkil, -SO3-M+, -SR10 ili -(C=W)R11; ili C1-C6 alkil ili C1-C6 haloalkil, svaki izborno supstituiran sa do 2 R12;
R5 je H, C1-C6 alkil ili C1-C6 haloalkil;
R6 i R7 su nezavisno izabrani od H, C1-C6 alkil, C1-C6 haloalkil, C3-C7 cikloalkil, C4-C8 cikloalkilalkil i C4-C8 alkilcikloalkil; ili
R6 i R7 su povezani sa atomom dušika za koji su vezani tako da formiraju četvoro- do sedmo-člani nearomatični heterociklični prsten koji sadrži članove prstena, pored atoma dušika koji povezuje prsten, izabrane od atoma ugljika i izborno do jedan član prstena izabran od O, S(O)n i NR13;
svaki R8, R9a i R9b je nezavisno izabran od halogena, C1-C2 alkil, C1-C2 haloalkil, C1-C2 alkoksi, C1-C2 haloalkoksi, cijano, nitro, SCH3, S(O)CH3 i S(O)2CH3;
R10 je C1-C6 alkil ili C1-C6 haloalkil;
R11 je C1-C6 alkil, C1-C6 alkoksi, C2-C7 alkoksialkil, C2-C7 alkilaminoalkil, C3-C8 dialkilaminoalkil, C1-C6 alkiltio ili C2-C7 alkiltioalkil;
svaki R12 je nezavisno C3-C7 cikloalkil, C1-C4 alkoksi, C1-C4 haloalkoksi, C1-C4 alkiltio, C1-C4 alkilsulfinil ili C1-C4 alkilsulfonil;
R13 je H, C1-C3 alkil ili C2-C3 haloalkil;
W je O ili S;
M+ je kation;
m je 0, 1 ili 2; i
n je 0, 1 ili 2.
9. Spoj prema patentnom zahtjevu 8 u kojem
Q1 je fenil, piridinil, pirimidinil, pirazinil ili piridazinil, svaki supstituiran sa od 1 do 4 supstituenta nezavisno izabrana od R3;
Q2 je fenil, piridinil, pirimidinil, pirazinil ili piridazinil, svaki supstituiran sa 1, 2 ili 3 supstituenta nezavisno izabrana od R3
X je O ili NR4;
R1 je H, halogen, C1-C6 alkil, C1-C6 haloalkil, CO2R5, C(O)NR6R7, cijano, C1-C6 alkoksi, C1-C6 haloalkoksi ili C2-C5 alkoksialkil; ili
R1 je pet- ili šesto-člani aromatični heterociklus koji sadrži dušik izborno supstituiran sa do 3 supstituenta nezavisno izabrana od R9a na članovima prstena koji su atomi ugljika i R9b na članovima prstena koji su atomi dušika;
R2 je CH3, CH2CH3, Cl ili Br;
svaki R3 je nezavisno izabran od halogena, cijano, amino, metilamino, dimetilamino, C1-C4 alkil, C1-C4 haloalkil, C1-C3 alkoksi, C1-C3 haloalkoksi C1-C3 alkiltio, C1-C3 haloalkiltio, C1-C3 alkilsulfinil, C1-C3 haloalkilsulfinil, C1-C3 alkilsulfonil, C1-C3 haloalkilsulfonil i C3-C4 cikloalkil;
R4 je H, formil, C3-C7 cikloalkil ili -SR10; ili C1-C6 alkil ili C1-C6 haloalkil, svaki izborno supstituiran sa do 2 R12;
R5 je H ili C1-C6 alkil;
R6 je H ili C1-C6 alkil;
R7 je H, C1-C6 alkil, C1-C6 haloalkil ili C4-C8 alkilcikloalkil; ili
R6 i R7 povezani sa atomom dušika za koji su vezani tako da formiraju četvoro- do sedmo-člani nearomatični heterociklični prsten koji sadrži članove prstena, pored vežućeg atoma dušika, izabrane od atoma ugljika i do jedan član prstena izabran od O i NR13;
svaki R9a je nezavisno izabran od halogena, C1-C2 alkil, C1-C2 haloalkil, C1-C2 alkoksi, C1-C2 haloalkoksi, cijano i nitro;
svaki R9b je C1-C2 alkil;
R10 je CH3, CH2CH3, CF3 ili CF2CF3;
svaki R12 je nezavisno C3-C7 cikloalkil ili C1-C4 alkoksi; i
R13 je H ili CH3.
10. Spoj prema patentnom zahtjevu 8 ili 9 u kojem
Q1 je fenil ili piridinil, svaki supstituiran sa 1, 2 ili 3 supstituenta nezavisno izabrana od R3;
Q2 je fenil ili piridinil, svaki supstituiran sa 1, 2 ili 3 supstituenta nezavisno izabrana od R3;
X je NR4;
R1 je H, halogen, C1-C6 alkil, C1-C6 haloalkil, cijano, C1-C6 alkoksi ili C1-C6 haloalkoksi;
R2 je CH3;
svaki R3 je nezavisno izabran od halogena, cijano, C1-C4 alkil, C1-C4 haloalkil, C1-C3 alkoksi i C1-C3 haloalkoksi;
R4 je H, formil, C3-C7 cikloalkil ili -SR10; ili C1-C6 alkil supstituiran sa jednim R12; R10 je CH3; i
R12 je ciklopropil ili -OCH3.
11. Spoj prema patentnom zahtjevu 1 u kojem
Q1 je fenil supstituiran na 2- i 4-položajima sa supstituentima nezavisno izabranim od R3;
Q2 je fenil supstituiran na 2- i 6-položajima sa supstituentima nezavisno izabranim od R3;
X je NR4;
R1 je H;
R1a je H;
R2 je CH3;
svaki R3 je nezavisno izabran od F, Cl, Br i cijano; i
R4 je H.
12. Spoj prema patentnom zahtjevu 1 koji je izabran iz grupe:
4-(2-kloro-4-fluorofenil)-1,3-dimetil-N-(2,4,6-trifluorofenil)-1H-pirazol-5-amin,
N-(4-klorofenil)-4-(2,6-difluoro-4-metoksifenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2,6-difluoro-4-metoksifenil)-N-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2,6-difluoro-4-metoksifenil)-1,3-dimetil-N-(2,4,6-trifluorofenil)-1H-pirazol-5-amin,
N-(2,6-difluoro-4-metoksifenil)-4-(3,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2,4-difluorofenil)-1,3-dimetil-N-(2,4,6-trifluorofenil)-1H-pirazol-5-amin,
4-[[4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]-3,5-difluorobenzonitril,
4-[[4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]-3-fluorobenzonitril,
4-(2-kloro-4-fluorofenil)-N-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-[[4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]-3-fluorobenzonitril,
3-kloro-4-[[4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]benzonitril,
N,4-bis(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-kloro-4-fluorofenil)-4-(2-kloro-6-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-kloro-4,6-difluorofenil)-4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-kloro-4,6-difluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(4-kloro-2,6-difluorofenil)-4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(4-kloro-2,6-difluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
3-kloro-4-[[4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]benzonitril,
4-[[4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]amino]-3,5-difluoro-benzonitril,
4-[[4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]-2,5-difluoro-benzonitril,
N-(2-kloro-4-fluorofenil)-4-(2,6-difluoro-4-metoksifenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(4-kloro-2,6-difluorofenil)-4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-kloro-4,6-difluorofenil)-4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2,6-dikloro-4-fluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
3-kloro-4-[5-[(2-kloro-4,6-difluorofenil)amino]-1,3-dimetil-1H-pirazol-4-il]-benzonitril,
3-kloro-4-[5-[(4-kloro-2,6-difluorofenil)amino]-1,3-dimetil-1H-pirazol-4-il]-benzonitril,
N-(2-bromo-4-fluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2-kloro-4-fluorofenil)-N-(2,4-dikloro-6-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2-kloro-4-fluorofenil)-N-(2,6-dikloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-[[4-(2-bromo-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]-3-fluorobenzonitril,
N-(2-bromo-4-fluorofenil)-4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2-bromo-4-fluorofenil)-1,3-dimetil-N-(2,4,6-trifluorofenil)-1H-pirazol-5-amin,
N-(4-bromo-2,6-difluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-[[4-(2-bromo-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]-3,5-difluoro-benzonitril,
4-(2-bromo-4-fluorofenil)-N-(2-kloro-4,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-(2-bromo-4-fluorofenil)-N-(4-kloro-2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(4-bromo-2,6-difluorofenil)-4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
3-bromo-4-[[4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]benzonitril,
3-kloro-4-[[4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-il]oksi]benzonitril,
N-(2,4-dikloro-6-fluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2,6-dikloro-4-fluorofenil)-4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-bromo-4,6-difluorofenil)-4-(2,4-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-bromo-4,6-difluorofenil)-4-(2-kloro-4-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(4-bromo-2,6-difluorofenil)-4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-bromo-4,6-difluorofenil)-4-(2,6-difluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
N-(2-bromo-4,6-difluorofenil)-4-(2-kloro-6-fluorofenil)-1,3-dimetil-1H-pirazol-5-amin,
4-[5-[(2-kloro-4,6-difluorofenil)amino]-1,3-dimetil-1H-pirazol-4-il]-3-fluorobenzonitril i
4-[5-[(4-kloro-2,6-difluorofenil)amino]-1,3-dimetil-1H-pirazol-4-il]-3-fluorobenzonitril.
13. Spoj prema patentnom zahtjevu 1 koji je 4-(2,6-difluoro-4-metoksifenil)-1,3-dimetil-N-(2,4,6-trifluorofenil)-1H-pirazol-5-amin.
14. Fungicidna kompozicija koja sadrži (a) spoj prema bilo kojem od patentnih zahtjeva 1 do 13 ili spoj izabran od 2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenola; 2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenola;
[image]
2-(1,3-dimetil-4-fenilpirazolil)amino-2-imidazolin HCl; metil (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi[fenoksi)propionske kiseline; metil (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata; (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline; metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi[fenoksi)propionske kiseline; metil (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata; (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; i metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionata
i (b) najmanje jedan drugi fungicid.
15. Kompozicija prema patentnom zahtjevu 14 u kojoj je komponenta (b) izabrana od protiokonazola, metkonazola, pentiopirada i klorotalonila.
16. Fungicidna kompozicija koja sadrži: (a) spoj prema bilo kojem od patentnih zahtjeva 1 do 13; i (b) najmanje jednu dodatnu komponentu izabranu iz grupe koja se sastoji od surfaktanata, čvrstih razblaživača i tekućih razblaživača.
17. Postupak za kontrolu biljnih bolesti uzrokovanih gljivičnim biljnim patogenima koji sadrži nanošenje na biljku ili njen dio, ili na sjeme biljke, fungicidno efikasne količine spoja prema bilo kojem od patentnih zahtjeva 1 do 13 ili spoja izabranog od 2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenola; 2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenola;
[image]
2-(1,3-dimetil-4-fenilpirazolil)amino-2-imidazolin HCl; metil (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; metil (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata; (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline; metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi[fenoksi)propionske kiseline; metil (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata; (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; i metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionata.
18. Kompozicija koja sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 13 ili spoj izabran od 2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenola; 2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenola;
[image]
2-(1,3-dimetil-4-fenilpirazolil)amino-2-imidazolin HCl; metil (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[4-(izoksazol-3-il)-1,3-dimetil-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; metil (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata; (2S)-2-[2,4-dikloro-5-({4-[5-(hidroksimetil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline; metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metilizoksazol-3-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; metil (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionata; (2S)-2-[2,4-dikloro-5-({4-[5-(1-hidroksi-1-metiletil)izoksazol-3-il]-1,3-dimetil-1H-pirazol-5-il}oksi)fenoksi]propionske kiseline; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(3-metil-1,2,4-oksadiazol-5-il)-1H-pirazol-5-il]oksi}fenoksi)propionata; (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionske kiseline; i metil (2S)-2-(2,4-dikloro-5-{[1,3-dimetil-4-(5-metil-1,3,4-tiadiazol-2-il)-1H-pirazol-5-il]oksi}fenoksi)propionata
i najmanje jedan spoj ili agens za kontrolu beskičmenjaka štetočine.
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