JP2008530059A - ピラゾールカルボキシアニリド、それらの製造方法及び有害菌を防除するためのそれらを含む組成物 - Google Patents
ピラゾールカルボキシアニリド、それらの製造方法及び有害菌を防除するためのそれらを含む組成物 Download PDFInfo
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- JP2008530059A JP2008530059A JP2007554584A JP2007554584A JP2008530059A JP 2008530059 A JP2008530059 A JP 2008530059A JP 2007554584 A JP2007554584 A JP 2007554584A JP 2007554584 A JP2007554584 A JP 2007554584A JP 2008530059 A JP2008530059 A JP 2008530059A
- Authority
- JP
- Japan
- Prior art keywords
- pyrazole
- methyl
- carboxamide
- dichlorobiphenyl
- trifluoromethyl
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims description 12
- 241000894006 Bacteria Species 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 239000000460 chlorine Substances 0.000 claims abstract description 41
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 34
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000011737 fluorine Substances 0.000 claims abstract description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 3
- -1 3 ′, 4′-dichlorobiphenyl-2-yl Chemical group 0.000 claims description 85
- 241000233866 Fungi Species 0.000 claims description 11
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 claims description 11
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 11
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 10
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 2
- KYXNOBUGJXDOIO-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(2,3,4-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1F KYXNOBUGJXDOIO-UHFFFAOYSA-N 0.000 claims 1
- SAEWEAKBGDVOPX-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F SAEWEAKBGDVOPX-UHFFFAOYSA-N 0.000 claims 1
- HDWGAKWQBOMENH-UHFFFAOYSA-N 1-methyl-3-(trifluoromethyl)-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 HDWGAKWQBOMENH-UHFFFAOYSA-N 0.000 claims 1
- OXBRSAWHLLAWFH-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F OXBRSAWHLLAWFH-UHFFFAOYSA-N 0.000 claims 1
- UIMRMZWPXAGXRL-UHFFFAOYSA-N 3-(fluoromethyl)-1-methyl-n-[2-(2,3,4-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1F UIMRMZWPXAGXRL-UHFFFAOYSA-N 0.000 claims 1
- JKGGFKZHTXQAPJ-UHFFFAOYSA-N 3-(fluoromethyl)-1-methyl-n-[2-(2,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C=C1F JKGGFKZHTXQAPJ-UHFFFAOYSA-N 0.000 claims 1
- ACGQBCAWGUDTQW-UHFFFAOYSA-N 3-(fluoromethyl)-1-methyl-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 ACGQBCAWGUDTQW-UHFFFAOYSA-N 0.000 claims 1
- FDYQKQCEOKOFLX-UHFFFAOYSA-N 3-chloro-5-(difluoromethyl)-1-methyl-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=C(F)C=2)=C1C(F)F FDYQKQCEOKOFLX-UHFFFAOYSA-N 0.000 claims 1
- FAUNUHHYLCHKQZ-UHFFFAOYSA-N 3-chloro-5-(difluoromethyl)-n-[2-(3,4-difluorophenyl)phenyl]-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=CC=2)=C1C(F)F FAUNUHHYLCHKQZ-UHFFFAOYSA-N 0.000 claims 1
- QVEBGUHTZIXVCR-UHFFFAOYSA-N 3-chloro-5-(fluoromethyl)-1-methyl-n-[2-(3,4,5-trifluorophenyl)phenyl]pyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=C(F)C=2)=C1CF QVEBGUHTZIXVCR-UHFFFAOYSA-N 0.000 claims 1
- VGHWDCNCTJOJIF-UHFFFAOYSA-N 3-chloro-n-[2-(2,4-dichlorophenyl)phenyl]-5-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1C(F)F VGHWDCNCTJOJIF-UHFFFAOYSA-N 0.000 claims 1
- HHAKCXBCFACUBA-UHFFFAOYSA-N 3-chloro-n-[2-(2,4-dichlorophenyl)phenyl]-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CF HHAKCXBCFACUBA-UHFFFAOYSA-N 0.000 claims 1
- FAHMVDDDNZUPQO-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dichlorophenyl)phenyl]-5-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1C(F)F FAHMVDDDNZUPQO-UHFFFAOYSA-N 0.000 claims 1
- ZSKYXFNHIIXGMQ-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dichlorophenyl)phenyl]-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1CF ZSKYXFNHIIXGMQ-UHFFFAOYSA-N 0.000 claims 1
- FIGWCTZVADTDHS-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-difluorophenyl)phenyl]-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(F)C(F)=CC=2)=C1CF FIGWCTZVADTDHS-UHFFFAOYSA-N 0.000 claims 1
- RUONVFKSWMDXFO-UHFFFAOYSA-N 3-chloro-n-[2-(3,5-dichlorophenyl)phenyl]-5-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C=C(Cl)C=2)=C1C(F)F RUONVFKSWMDXFO-UHFFFAOYSA-N 0.000 claims 1
- PKBDSECDWXSKOB-UHFFFAOYSA-N 3-chloro-n-[2-(3,5-dichlorophenyl)phenyl]-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C=C(Cl)C=2)=C1CF PKBDSECDWXSKOB-UHFFFAOYSA-N 0.000 claims 1
- UGMYXPMXPMGVNG-UHFFFAOYSA-N 3-chloro-n-[2-(3-chloro-4-fluorophenyl)phenyl]-5-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(F)=CC=2)=C1C(F)F UGMYXPMXPMGVNG-UHFFFAOYSA-N 0.000 claims 1
- JVELVOBIUWFPPF-UHFFFAOYSA-N 3-chloro-n-[2-(3-chloro-4-fluorophenyl)phenyl]-5-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(Cl)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(F)=CC=2)=C1CF JVELVOBIUWFPPF-UHFFFAOYSA-N 0.000 claims 1
- FFYYPDXADZDSIY-UHFFFAOYSA-N 5-chloro-n-[2-(2,4-dichlorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(Cl)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1Cl FFYYPDXADZDSIY-UHFFFAOYSA-N 0.000 claims 1
- GVWKFKMPOKPXCT-UHFFFAOYSA-N 5-chloro-n-[2-(3,4-dichlorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(Cl)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 GVWKFKMPOKPXCT-UHFFFAOYSA-N 0.000 claims 1
- NDQHMXJJCBINJT-UHFFFAOYSA-N 5-chloro-n-[2-(3,5-dichlorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(Cl)=C1C(=O)NC1=CC=CC=C1C1=CC(Cl)=CC(Cl)=C1 NDQHMXJJCBINJT-UHFFFAOYSA-N 0.000 claims 1
- LZJOUHXBVDDXMJ-UHFFFAOYSA-N 5-chloro-n-[2-(3-chloro-4-fluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C(Cl)=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 LZJOUHXBVDDXMJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 claims 1
- LNVMONUUECOFJK-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1Cl LNVMONUUECOFJK-UHFFFAOYSA-N 0.000 claims 1
- YOPXZBWREKQXDJ-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1Cl YOPXZBWREKQXDJ-UHFFFAOYSA-N 0.000 claims 1
- OUWQEPAMELJVQI-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CN1N=C(C(F)(F)F)C(C(=O)NC=2C(=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1F OUWQEPAMELJVQI-UHFFFAOYSA-N 0.000 claims 1
- JURSJSXKJRFATH-UHFFFAOYSA-N n-[2-(2,4-difluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C=C1F JURSJSXKJRFATH-UHFFFAOYSA-N 0.000 claims 1
- DQJNKMOIDDTGSF-UHFFFAOYSA-N n-[2-(2,4-difluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C=C1F DQJNKMOIDDTGSF-UHFFFAOYSA-N 0.000 claims 1
- XAWOJDGFEAAMHF-UHFFFAOYSA-N n-[2-(2-chloro-4-fluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C=C1Cl XAWOJDGFEAAMHF-UHFFFAOYSA-N 0.000 claims 1
- UUVUCSGVBHFBQG-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 UUVUCSGVBHFBQG-UHFFFAOYSA-N 0.000 claims 1
- CCDYOZVXAYEUFX-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(Cl)=C1 CCDYOZVXAYEUFX-UHFFFAOYSA-N 0.000 claims 1
- HYPQOPSPZIIVQA-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CN1N=C(C(F)(F)F)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)=C1F HYPQOPSPZIIVQA-UHFFFAOYSA-N 0.000 claims 1
- FLUBDYDVWLXMIO-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)phenyl]-n,1-dimethyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=CC=C(C=2C=C(Cl)C(Cl)=CC=2)C=1N(C)C(=O)C1=CN(C)N=C1C(F)(F)F FLUBDYDVWLXMIO-UHFFFAOYSA-N 0.000 claims 1
- YZUZBQNRPMSDFO-UHFFFAOYSA-N n-[2-(3,4-difluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1 YZUZBQNRPMSDFO-UHFFFAOYSA-N 0.000 claims 1
- CQKDEOFQMSSMLC-UHFFFAOYSA-N n-[2-(3,4-difluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(F)=C1 CQKDEOFQMSSMLC-UHFFFAOYSA-N 0.000 claims 1
- FFMSNYHJGXXFSP-UHFFFAOYSA-N n-[2-(3,5-dichlorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(Cl)=CC(Cl)=C1 FFMSNYHJGXXFSP-UHFFFAOYSA-N 0.000 claims 1
- APJZPIZGLMSILC-UHFFFAOYSA-N n-[2-(3,5-dichlorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(Cl)=CC(Cl)=C1 APJZPIZGLMSILC-UHFFFAOYSA-N 0.000 claims 1
- YSPYDPLBYANXHG-UHFFFAOYSA-N n-[2-(3,5-dichlorophenyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CN1N=C(C(F)(F)F)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C=C(Cl)C=2)=C1F YSPYDPLBYANXHG-UHFFFAOYSA-N 0.000 claims 1
- VJUCIOAMLJYDIU-UHFFFAOYSA-N n-[2-(3,5-difluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=CC(F)=C1 VJUCIOAMLJYDIU-UHFFFAOYSA-N 0.000 claims 1
- QZSOGVPPEUVOMD-UHFFFAOYSA-N n-[2-(3-chloro-4-fluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 QZSOGVPPEUVOMD-UHFFFAOYSA-N 0.000 claims 1
- VGTYWJSHPTZEBT-UHFFFAOYSA-N n-[2-(3-chloro-4-fluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(F)C(Cl)=C1 VGTYWJSHPTZEBT-UHFFFAOYSA-N 0.000 claims 1
- FMYOFKHFZQKCRX-UHFFFAOYSA-N n-[2-(3-chloro-4-fluorophenyl)phenyl]-5-fluoro-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CN1N=C(C(F)(F)F)C(C(=O)NC=2C(=CC=CC=2)C=2C=C(Cl)C(F)=CC=2)=C1F FMYOFKHFZQKCRX-UHFFFAOYSA-N 0.000 claims 1
- YDIKXIAWBNOAJY-UHFFFAOYSA-N n-[2-(4-chloro-2-fluoro-5-methoxyphenyl)phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(C=2C(=CC=CC=2)NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1F YDIKXIAWBNOAJY-UHFFFAOYSA-N 0.000 claims 1
- SZZZJBWZTNVKGT-UHFFFAOYSA-N n-[2-(4-chloro-2-fluoro-5-methoxyphenyl)phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound C1=C(Cl)C(OC)=CC(C=2C(=CC=CC=2)NC(=O)C=2C(=NN(C)C=2)C(F)F)=C1F SZZZJBWZTNVKGT-UHFFFAOYSA-N 0.000 claims 1
- ILKDFYNYRDQIQC-UHFFFAOYSA-N n-[2-(4-chloro-2-fluoro-5-methylphenyl)phenyl]-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=C(Cl)C(C)=CC(C=2C(=CC=CC=2)NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1F ILKDFYNYRDQIQC-UHFFFAOYSA-N 0.000 claims 1
- MREJHKBZVBNCSF-UHFFFAOYSA-N n-[2-(4-chloro-2-fluoro-5-methylphenyl)phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound C1=C(Cl)C(C)=CC(C=2C(=CC=CC=2)NC(=O)C=2C(=NN(C)C=2)C(F)F)=C1F MREJHKBZVBNCSF-UHFFFAOYSA-N 0.000 claims 1
- HKSSZINUCWGBDI-UHFFFAOYSA-N n-[2-(4-chloro-2-fluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1F HKSSZINUCWGBDI-UHFFFAOYSA-N 0.000 claims 1
- BKLOBHBLSLVROM-UHFFFAOYSA-N n-[2-(4-chloro-2-fluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C=C1F BKLOBHBLSLVROM-UHFFFAOYSA-N 0.000 claims 1
- YIAMSKIDFVFIBD-UHFFFAOYSA-N n-[2-(4-chloro-3-fluorophenyl)phenyl]-1,3-dimethylpyrazole-4-carboxamide Chemical compound CC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(F)=C1 YIAMSKIDFVFIBD-UHFFFAOYSA-N 0.000 claims 1
- IUVUUOONLCKAHR-UHFFFAOYSA-N n-[2-(4-chloro-3-fluorophenyl)phenyl]-3-(fluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FCC1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(F)=C1 IUVUUOONLCKAHR-UHFFFAOYSA-N 0.000 claims 1
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- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- QTYCMDBMOLSEAM-UHFFFAOYSA-N ipconazole Chemical compound C1=NC=NN1CC1(O)C(C(C)C)CCC1CC1=CC=C(Cl)C=C1 QTYCMDBMOLSEAM-UHFFFAOYSA-N 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- WLPCAERCXQSYLQ-UHFFFAOYSA-N isotianil Chemical compound ClC1=NSC(C(=O)NC=2C(=CC=CC=2)C#N)=C1Cl WLPCAERCXQSYLQ-UHFFFAOYSA-N 0.000 description 1
- JPUKWEQWGBDDQB-DTGCRPNFSA-N kaempferol 3-O-beta-D-galactoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O JPUKWEQWGBDDQB-DTGCRPNFSA-N 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- CIFWZNRJIBNXRE-UHFFFAOYSA-N mepanipyrim Chemical compound CC#CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 CIFWZNRJIBNXRE-UHFFFAOYSA-N 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N metam Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- ZDDLQZXLOXYKLT-UHFFFAOYSA-N methyl 2-[6-[(2,5-dimethylphenoxy)methylidene]cyclohexa-2,4-dien-1-yl]-3-methoxyprop-2-enoate Chemical compound COC=C(C(=O)OC)C1C=CC=CC1=COC1=CC(C)=CC=C1C ZDDLQZXLOXYKLT-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SMBBZHGTZJNSRQ-UHFFFAOYSA-N n'-(6,6-dichlorohexyl)methanediimine Chemical compound ClC(Cl)CCCCCN=C=N SMBBZHGTZJNSRQ-UHFFFAOYSA-N 0.000 description 1
- JVRMUFJCFLXSMJ-UHFFFAOYSA-N n,2-diphenylbenzamide Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)NC1=CC=CC=C1 JVRMUFJCFLXSMJ-UHFFFAOYSA-N 0.000 description 1
- KNHFGNGQAPKHOC-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)-5-fluorophenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC(F)=CC=C1C1=CC=C(Cl)C(Cl)=C1 KNHFGNGQAPKHOC-UHFFFAOYSA-N 0.000 description 1
- NOTMCFVPRDIUAV-UHFFFAOYSA-N n-[2-(4-bromophenyl)phenyl]-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Br)C=C1 NOTMCFVPRDIUAV-UHFFFAOYSA-N 0.000 description 1
- AYVPXJFRSYHRJX-UHFFFAOYSA-N n-[2-(4-chloro-3-fluorophenyl)phenyl]-4-(difluoromethyl)-2-methyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C)=NC(C(F)F)=C1C(=O)NC1=CC=CC=C1C1=CC=C(Cl)C(F)=C1 AYVPXJFRSYHRJX-UHFFFAOYSA-N 0.000 description 1
- JCPCLLBVKYTARN-UHFFFAOYSA-N n-[2-[4-[3-(4-chlorophenyl)prop-2-ynoxy]-3-methoxyphenyl]ethyl]-2-(ethylsulfonylamino)-3-methylbutanamide Chemical compound COC1=CC(CCNC(=O)C(C(C)C)NS(=O)(=O)CC)=CC=C1OCC#CC1=CC=C(Cl)C=C1 JCPCLLBVKYTARN-UHFFFAOYSA-N 0.000 description 1
- BOBIZDGUDNVINH-UHFFFAOYSA-N n-[2-[4-[3-(4-chlorophenyl)prop-2-ynoxy]-3-methoxyphenyl]ethyl]-2-(methanesulfonamido)-3-methylbutanamide Chemical compound COC1=CC(CCNC(=O)C(NS(C)(=O)=O)C(C)C)=CC=C1OCC#CC1=CC=C(Cl)C=C1 BOBIZDGUDNVINH-UHFFFAOYSA-N 0.000 description 1
- XOBQFDDBNJLYFA-UHFFFAOYSA-N n-[5-chloro-2-(3-chlorophenyl)phenyl]-3-[dichloro(fluoro)methyl]-1-methylpyrazole-4-carboxamide Chemical compound FC(Cl)(Cl)C1=NN(C)C=C1C(=O)NC1=CC(Cl)=CC=C1C1=CC=CC(Cl)=C1 XOBQFDDBNJLYFA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-N 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000005687 scabies Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Insulated Conductors (AREA)
Abstract
Description
nはゼロ又は2であり;
mは2又は3であり;
X1はフッ素又は塩素であり;
X2はハロゲンであり;
YはCN、NO2、C1-C4-アルキル、C1-C4-ハロアルキル、メトキシ又はメチルチオであり;
pはゼロ又は1であり;
R1はフッ素、塩素、臭素、C1-C4-アルキル又はC1-C4-ハロアルキルであり;
R2は水素又はハロゲンであり;
R3は水素、メチル又はエチルであり;
WはO又はSであり;
但し、
a)W=O、R1=メチル、そしてR3が水素であるならば、R2はFではなく、又は
b)W=O、n=0、m=2、p=0、R2及びR3が水素であるならば、R1はトリフルオロメチル又はジフルオロメチルではない)に関する。
C1-C4-アルキルは、メチル、エチル、n-プロピル、1-メチルエチル、n-ブチル、1-メチルプロピル、2-メチルプロピル又は 1,1-ジメチルエチル、好ましくはメチル又はエチルであり;
C1-C4-ハロアルキルは、部分的又は完全にハロゲン化されたC1-C4-アルキル基であり、ここで、ハロゲン原子は特にフッ素及び/又は塩素であり、すなわち、例えば、クロロメチル、ブロモメチル、ジクロロメチル、トリクロロメチル、フルオロメチル、ジフルオロメチル、トリフルオロメチル、クロロフルオロメチル、ジクロロフルオロメチル、クロロジフルオロメチル、1-クロロエチル、1-ブロモエチル、1-フルオロエチル、2-フルオロエチル、2,2-ジフルオロエチル、2-クロロ-2-フルオロエチル、2,2,2-トリフルオロエチル、2-クロロ-1,1,2-トリフルオロエチル、2-クロロ-2,2-ジフルオロエチル、2-ブロモ-2,2-ジフルオロエチル、2,2-ジクロロ-2-フルオロエチル、2,2,2-トリクロロエチル、1,1,2,2-テトラフルオロエチル、1,1,2,2-テトラクロロエチル、ペンタフルオロエチル、2,2,3,3-テトラフルオロ-1-プロピル、1,1,2,3,3,3-ヘキサフルオロ-1-プロピル、1,1,1,3,3,3-ヘキサフルオロ-2-プロピル、ヘプタフルオロ-1-プロピル、ヘプタフルオロ-2-プロピル、2,2,3,3,4,4,4-ヘプタフルオロ-1-ブチル又はノナフルオロ-1-ブチル、特にハロメチルであり、CH2-Cl、CH(Cl)2 、CH2-F、CH(F)2 、CF3 、CHFCl、CF2Cl 又は CF(Cl)2 が特に好ましい。
プロピル)-N'-エチルカルボジイミドカルボジイミドである。
nはゼロであり;
mは3であり;
X1は塩素であり;
X2はフッ素又は塩素、好ましくはフッ素であり;
YはC1-C4-アルキル、C1-C4-ハロアルキル又はメトキシ、特に
メチル、ジフルオロメチル、トリフルオロメチル又はメトキシ;
特に好ましくはメチル又はトリフルオロメチルであり;
pはゼロであり;
R1はフッ素、塩素、C1-C4-アルキル又はC1-C4-ハロアルキル、特にF、Cl、 メチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチル;
特に好ましくはメチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル又はトリフルオロメチル、とりわけジフルオロメチル又はトリフルオロメチル;
実に特に好ましくはジフルオロメチルであり;
R2は水素、フッ素又は塩素、特に水素又は塩素、特に好ましくは水素であり;
R3は水素又はメチル、特に水素であり;
Wは酸素である。
X2はフッ素又は塩素であり;
Yはメチル、ジフルオロメチル、トリフルオロメチル又はメトキシであり;
R1はF、塩素、メチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル、トリフルオロメチルであり;
R2は水素、フッ素又は塩素であり;
R3は水素又はメチルであり;
Wは酸素である。
nはゼロであり;
pはゼロであり;
R1はF、塩素、メチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチル、特にフッ素、塩素、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチルであり;
R2は水素、フッ素又は塩素であり;
R3は水素であり;
Wは酸素である。
R2、R3が水素であり、そしてそれぞれ個々の化合物のためのR1及びBが何れの場合にも表Aの一つの列(列1〜22及び67〜88を除く)に対応する一般式I-A の化合物。
R2がClであり、R3が水素であり、そしてそれぞれ個々の化合物のためのR1及びBが何れの場合にも表Aの一つの列に対応する一般式I-A の化合物。
R2がFであり、R3が水素であり、そしてそれぞれ個々の化合物のためのR1及びBが何れの場合にも表Aの一つの列(列397〜462を除く)に対応する一般式I-A の化合物。
R2が水素であり、R3がメチルであり、そしてそれぞれ個々の化合物のためのR1及びBが何れの場合にも表Aの一つの列に対応する一般式I-A の化合物。
R2が水素であり、R3がエチルであり、そしてそれぞれ個々の化合物のためのR1及びBが何れの場合にも表Aの一つの列に対応する一般式I-A の化合物。
R2が水素であり、そしてそれぞれ個々の化合物のためのR1及びBが何れの場合にも表Aの一つの列に対応する一般式I-B の化合物。
それぞれ個々の化合物のためのBが何れの場合にも表Bの一つの列に対応する一般式I-C の化合物。
それぞれ個々の化合物のためのBが何れの場合にも表Bの一つの列に対応する一般式I-D の化合物。
- 野菜、ナタネ、テンサイ及び果実及びイネにおけるアルテルナリア属(Alternaria)の種(例えばジャガイモ及び他の植物における A. ソラニ(A. solani) 又は A. アルテルナタ (A. alternata))、
- テンサイ及び野菜におけるアファノマイセス属(Aphanomyces)の種、
- トウモロコシ、穀物、イネ及びシバフにおけるビポラリス属(Bipolaris)及びドレクスレラ属(Drechslera)の種(例えばオオムギにおける D. テレス(D. teres)、コムギにおける D. トリシ-レペンチス(D. trici-repentis))、
- 穀物におけるブルメリア・グラミニス(Blumeria graminis)(ウドンコ病)、
- イチゴ、野菜、花及びブドウのつるにおけるボトリチス・シネレア(Botrytis cinerea)(灰色かび病)、
- レタスにおけるブレミア・ラクツカエ(Bremia lactucae)、
- トウモロコシ、ダイズ、イネ及びテンサイにおけるセルコスポラ属(Cercospora)の種(例えばテンサイにおける C. ベチクラ(C. beticula))、
- トウモロコシ、穀物、イネにおけるコクリオボルス属(Cochliobolus)の種(例えば穀物におけるコクリオボルス・サチブス(Cochliobolus sativus)、イネにおけるコクリオボルス・ミヤベアヌス(Cochliobolus miyabenus))、
- ダイズ、ワタ及び他の植物におけるコレトトリクム属(Colletotricum)の種(例えば種々の植物における C. アクタツム(C. acutatum))、
- トウモロコシにおけるエクセロヒルム属(Exserohilum)の種、
- ウリにおけるエリシフェ・シコラセアルム(Erysiphe cichoracearum)及びスフェロテカ・フリギネア(Sphaerotheca fuliginea)、
- 種々の植物におけるフザリウム属(Fusarium)及びベルチシリウム属(Verticillium)の種(例えばコムギにおける F. グラミネアルム(F. graminearum))、
- 穀物におけるゲウマノマイセス・グラミニス(Gaeumanomyces graminis)、
- 穀物及びイネにおけるギベレラ属(Gibberella)の種(例えばイネにおけるギベレラ・フジクロイ(Gibberella fujikuroi))、
- イネにおける穀粒染色コンプレックス、
- トウモロコシ及びイネにおけるヘルミントスポリウム属(Helminthosporium)の種(例えば H. グラミニコラ(H. graminicola))、
- 穀物におけるミクロドキウム・ニバレ(Michrodochium nivale)、
- 穀物、バナナ及びラッカセイにおけるマイコスフェレラ属(Mycosphaerella)の種(例えばコムギにおける M. グラミニコラ(M. graminicola)、バナナにおける M. フィジエシス(M. fijiesis))、
- ダイズにおけるファコプサラ・パキリジ(Phakopsara pachyrhizi)及びファコプサラ・メイボミエ(Phakopsara meibomiae)、
- ダイズ、ヒマワリ及びブドウのつるにおけるフォモプシス属(Phomopsis)の種(ブドウのつるにおける P. ビチコラ(P. viticola)、ヒマワリにおける P. ヘリアンチイ(P. helianthii))、
- ジャガイモ及びトマトにおけるフィトフトラ・インフェスタンス(Phytophthora infestans)、
- ブドウのつるにおけるプラスモパラ・ビチコラ(Plasmopara viticola)、
- リンゴにおけるポドスフェラ・ロイコトリカ(Podosphaera leucotricha)、
- 穀物におけるシュードセルコスポレラ・ヘルポトリコイデス(Pseudocercosporella herpotrichoides)、
- ホップ及びウリにおけるシュードペロノスポラ属(Pseudoperonospora)の種(例えばキュウリにおける P. クベニス(P. cubenis))、
- 穀物、トウモロコシ及びアスパラガスにおけるプッチニア属(Puccinia)の種(コムギにおける P. トリチシナ(P. triticina)及び P. ストリホルミス(P. striformis)、アスパラガスにおける P. アスパラギ(P. asparagi))、
- 穀物におけるピレノフォラ属(Pyrenophora)の種、
- イネにおけるピリクラリア・オリゼ(Pyricularia oryzae)、コルチシウム・サカキイ(Corticium sasakii)、サロクラディウム・オリゼ(Sarocladium oryzae)、S. アテヌアツム(S.attenuatum)、エンチロマ・オリゼ(Entyloma oryzae)、
- シバフ及び穀物におけるピリクラリア・グリセア(Pyricularia grisea)、
- シバフ、イネ、トウモロコシ、ワタ、ナタネ、ヒマワリ、テンサイ、野菜及び他の植物におけるピチウム spp.( Pythium spp.)、
- ワタ、イネ、ジャガイモ、シバフ、トウモロコシ、ナタネ、ジャガイモ、テンサイ、野菜及び他の植物におけるリゾクトニア属(Rhizoctonia)の種(例えば R. ソラニ(R. solani))、
- ナタネ、ヒマワリ及び他の植物におけるスクレロチニア属(Sclerotinia species)の種(例えば S. スクレロチオルム(S. sclerotiorum))、
- コムギにおけるセプトリア・トリチシ(Septoria tritici)及びスタゴノスポラ・ノドルム(Stagonospora nodorum)、
- ブドウのつるにおけるエリシフェ(Erysiphe)(ウンシヌアネカトル(Uncinulanecator)と同義)、
- トウモロコシ及びシバフにおけるセトスペリア属(Setospaeria)の種、
- トウモロコシにおけるスファセロテカ・レイリニア(Sphacelotheca reilinia)、
- ダイズ及びワタにおけるチエバリオプシス属(Thievaliopsis)の種、
- 穀物におけるチレチア属(Tilletia)の種、
- 穀物、トウモロコシ及びテンサイにおけるウスチラゴ属(Ustilago)の種、並びに
- リンゴ及びナシにおけるベンツリア属(Venturia)の種(疥癬)(例えばリンゴにおける V. イネクアリス(V. inaequalis))。
- 水、芳香族溶剤(例えば Solvesso 製品、キシレン)、パラフィン(例えば鉱油留分)、アルコール(例えばメタノール、ブタノール、ペンタノール、ベンジルアルコール)、ケトン(例えばシクロヘキサノン、ガンマ-ブチロラクトン)、ピロリドン(NMP、NOP)、アセテート(例えばグリコールジアセテート)、グリコール、脂肪酸ジメチルアミド、脂肪酸及び脂肪酸エステル。原則として、溶剤混合物を使用することもできる、
- 担体、例えば粉砕天然鉱物(例えばカオリン、クレー、タルク、チョーク)及び粉砕合成鉱物(例えば高分散シリカ、シリケート);乳化剤、例えば非イオン及び陰イオン乳化剤(例えばポリオキシエチレン脂肪アルコールエーテル、アルキルスルホネート及びアリールスルホネート)、並びに分散剤、例えばリグノ亜硫酸塩廃液及びメチルセルロース。
A) 水溶性濃縮物 (SL)
10重量部の本発明に係る化合物Iを90重量部の水又は水溶性溶剤に溶解する。別法として、湿潤剤又の助剤を加える。水で希釈すると、活性化合物は溶解する。このようにして、10重量%の活性化合物濃度を有する製剤が得られる。
20重量部の本発明に係る化合物Iを70重量部シクロヘキサノンに、10重量部の分散剤、例えばポリビニルピロリドンを加えて溶解する。水で希釈すると、分散液を与える。活性化合物含有量は20重量%である。
15重量部の本発明に係る化合物Iを75重量部のキシレンに、ドデシルベンゼンスルホン酸カルシウム及びヒマシ油エトキシル化物(それぞれの場合5重量部)を加えて溶解する。水で希釈すると、エマルジョンを与える。この製剤は15重量%の活性化合物含有量を有する。
25重量部の本発明に係る化合物Iを35重量部のキシレンに、ドデシルベンゼンスルホン酸カルシウム及びヒマシ油エトキシル化物(それぞれの場合5重量部)を加えてに溶解する。この混合物を乳化装置 (例えば Ultraturax) により30重量部の水中に導入し、均質なエマルジョンにする。水で希釈すると、エマルジョンを与える。この製剤は25重量%の活性化合物含有量を有する。
攪拌式ボールミル中で、20重量部の本発明に係る化合物Iを、10重量部の分散剤及び湿潤剤並びに70重量部の水又は有機溶剤を加えて粉砕して微細活性化合物懸濁液を与える。水で希釈すると、活性化合物の安定な懸濁液を与える。この製剤の活性化合物含有量は20重量%である。
50重量部の本発明に係る化合物Iを、50重量部の分散剤及び湿潤剤を加えて微細に粉砕し、工業的装置(例えば押し出し機、噴霧塔、流動床)により水分散性又は水溶性顆粒として製造する。水で希釈すると、活性化合物の安定な分散液又は溶液を与える。この製剤は50重量%の活性化合物含有量を有する。
75重量部の本発明に係る化合物Iを、ローター-ステーターミル中で、20重量部の分散剤、湿潤剤及びシリカゲルを加えて粉砕する。水で希釈すると、活性化合物の安定な分散液又は溶液を与える。この製剤の活性化合物含有量は75重量%である。
H) 散布可能な粉末 (DP)
5重量部の本発明に係る化合物Iを微細に粉砕し、95%の微粉カオリンと緊密に混合する。これは5重量%の活性化合物含有量を有する散布可能な生成物を与える。
0.5重量部の本発明に係る化合物Iを微細に粉砕し、95.5%の担体と関連させる。現在の方法は押し出し、噴霧乾燥又は流動床である。これは0.5重量%の活性化合物含有量を有する希釈せずに施用すべき顆粒を与える。
10重量部の本発明に係る化合物Iを90重量部の有機溶剤、例えばキシレンに溶解する。これは10重量%の活性化合物含有量を有する希釈せずに施用すべき生成物を与える。
ストロビルリン類
アゾキシストロビン、ジモキシストロビン、エネストロストロビン、フルオキサストロビン、クレゾキシム-メチル、メトミノストロビン、ピコキシストロビン、ピラクロストロビン、トリフロキシストロビン、オリザストロビン、(2-クロロ-5-[1-(3-メチルベンジルオキシイミノ)エチル]ベンジル)カルバミン酸メチル、(2-クロロ-5-[1-(6-メチルピリジン-2-イルメトキシイミノ)-エチル]ベンジル)カルバミン酸メチル、2-(オルト-(2,5-ジメチルフェニルオキシメチレン)フェニル)-3-メトキシアクリル酸メチル。
- カルボキシアニリド類:ベナラキシル、ベノダニル、ボスカリド、メプロニル、フェンフラム、フェンヘキサミド、フルトラニル、フラメトピル、メタラキシル、オフラーセ、オキサジキシル、オキシカルボキシン、ペンチオピラド、チフルザミド、チアジニル、N-(4’-ブロモビフェニル-2-イル)-4-ジフルオロメチル-2-メチルチアゾール-5-カルボキサミド、 N-(4’-トリフルオロメチルビフェニル-2-イル)-4-ジフルオロメチル-2-メチルチアゾール-5-カルボキサミド、 N-(4’-クロロ-3’-フルオロビフェニル-2-イル)-4-ジフルオロメチル-2-メチルチアゾール-5-カルボキサミド、 N-(3’,4’-ジクロロ-4-フルオロビフェニル-2-イル)-3-ジフルオロメチル-1-メチルピラゾール-4-カルボキサミド、 N-(2-シアノフェニル)-3,4-ジクロロイソチアゾール-5-カルボキサミド;
- カルボン酸モルホリド:ジメトモルフ、フルモルフ;
- ベンズアミド:フルメトベル、フルオピコリド(ピコベンズアミド)、ゾキサミド;
- 他のカルボキサミド類:カルプロパミド、ジクロシメト、マンジプロパミド、N-(2-(4-[3-(4-クロロフェニル)プロパ-2-インイルオキシ]-3-メトキシフェニル)エチル)-2-メタンスルホニルアミノ-3-メチルブチルアミド、N-(2-(4-[3-(4-クロロフェニル)プロパ -2-インイルオキシ]-3-メトキシフェニル)エチル)-2-エタンスルホニルアミノ-3-メチルブチルアミド;
アゾール類
- チアゾール類:ビテルタノール、ブムモコナゾール、シプロコナゾール、ジフェンコナゾール、ジニコナゾール、エニルコナゾール、エポキシコナゾール、フェンブコナゾール、フルシラゾール、フルキノコナゾール、フルトリアフォル、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メタコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、プロチオコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメノール、トリアジメフォン、トリチコナゾール;
- イミダゾール類:シアゾファミド、イマザリル、ペンフラゾエート、プロクロラズ、トリフルミゾール;
- ベンズイミダゾール類:ベノミル、カルベンダジンム、フベリダゾール、チアベンダゾール;
- その他:エタボキサム、エトリジアゾール、ヒメキサゾール;
含窒素ヘテロシクリル化合物
- ピリジン類:フルアジナム、ピリフェノクス、3-[5-(4-クロロフェニル)-2,3-ジメチルイソオキサゾリジン-3-イル]-ピリジン;
- ピリミジン類:ブピリメート、シプロジニル、フェリミゾン、フェナリモール、メパニピリム、ヌアリモール、ピリメタニル;
- ピペラジン類:トリフォリン;
- ピロール類:フルジオキソニル、フェンピクロニル;
- モルホリン類:アルジモルフ、ドデモルフ、フェンプロピモルフ、トリデモルフ;
- ジカルボキシイミド類:イプロジオン、プロシミドン、ビンクロゾリン
- その他:アシベンゾラー-S-メチル、アニラジン、カプタン、カプタフォール、ダゾメト、ジクロメジン、フェノキサニル、フォルペト、フェンプロピジン、ファモキサドン、フェナミドン、オクチリノン、プロベナゾール、プロキナゾール、プロキロン、キノキシフェン、トリシクラゾール、5-クロロ-7-(4-メチルピペリジン-1-イル)-6-(2,4,6-トリフルオロフェニル)-[1,2,4]トリアゾール[1,5-a]ピリミジン、2-ブトキシ-6-ヨード-3-プロピルクロメン-4-オン、N,N-ジメチル-3-(3-ブロモ-6-フルオロ-2-メチルインドール-1-スルホニル)-[1,2,4]トリアゾール-1-スルホンアミド;
カルバメート類及びジチオカルバメート類
- ジチオカルバメート類:フェルバム、マンコゼブ、マネブ、メチラム、メタム、プロピネブ、チラム、ジネブ、ジラム;
- カルバメート類:ジエトフェンカルブ、フルベンチアバリカルブ、イプロバリカルブ、プロパモカルブ、(4-クロロフェニル)-3-(2-イソプロポキシカルボニルアミノ-3-メチルブチリルアミノ)プロピオン酸メチル、N-(1-(1-(4-シアノフェニル)エタンスルホニル)ブタ-2-イル)カルバミン酸 4-フルオロフェニル;
他の殺菌剤
- グアニジン類:ドジン、イミノクタジン、グアザチン;
- 抗生物質:カスガマイシン、ポリオキシン、ストレプトマイシン、バリダマイシン A;
- 有機金属化合物:フェンチン塩;
- 硫黄含有ヘテロシクリル化合物:イソプロチオラン、ジチアノン;
- 有機リン化合物:エジフェンホス、フォセチル、フォセチル-アルミニウム、イプロベンフォス、ピラゾフォス、トルクロフォス-メチル、リン酸及びその塩;
- 有機塩素化合物:チオファネート-メチル、クロロタロニル、ジクロフルアニド、トリルフラニド、フルスルファミド、フタリド、ヘキサクロロベンゼン、ペンシクロン、キントゼン;
- ニトロフェニル誘導体:ビナパクリル、ジノカプ、フノブトン;
- 無機活性誘導体:ボルドー混合物、酢酸銅、水酸化銅、オキシ塩化銅、塩基性硫酸銅、硫黄;
- その他:スピロキサミン、シフルフェナミド、シモキサニル、メトラフェノン。
実施例1:
N-(3’-クロロ-4’-フルオロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド
室温で、3’-クロロ -4’-フルオロ-2-アミノビフェニル 0.47 g及びビス(2-オキソ-3-オキサゾリジニル)ホスホリルクロリド 0.82 g を、ジクロロメタン 30 ml 中の 1,3-ジメチル-1H-ピラゾール-4-カルボン酸 0.30 g 及びトリエチルアミン 0.43 g の溶液に加えた。この混合物を室温で12時間攪拌した。次いでこの混合物を順次に希塩酸で2回、重炭酸ナトリウム水溶液で2回及び水で1回洗浄した。有機相を乾燥し、濃縮した。粗生成物をシリカゲルカラムクロマトグラフィーによりシクロヘキサン/メチル tert-ブチルエーテル1:2を用いて精製した。これは目的生成物 0.56 g を融点177〜180℃の白色結晶として与えた。
N-(3'-クロロ -4'-フルオロビフェニル -2-イル)-3-フルオロメチル-1-メチル-1H-ピラゾール-4-カルボキサミド
室温で、3-フルオロメチル-1-メチル-1H-ピラゾール-4-カルボニルクロリド 0.27 g を、トルエン 10 ml 中の 3'-クロロ-4'-フルオロ-2-アミノビフェニル 0.33 g 及びピリジン 0.18 g の溶液に滴下し、この混合物を室温で16時間攪拌した。テトラヒドロフラン 10 ml 及びメチルtert-ブチルエーテル 30 ml を加え、有機相を順次に2%濃度の希塩酸で、2%濃度の水酸化ナトリウム水溶液で2回、次いで希塩化ナトリウム水溶液で洗浄した。有機相を乾燥し、減圧下に濃縮した。粗生成物をジイソプロピルエーテル 10 ml と共に磨砕し、残った固体を濾別し、乾燥した。これは目的生成物 0.46 g を融点133〜134℃の白色粉末として与えた。
N-(3',4'-ジクロロビフェニル-2-イル)メチル-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド
氷冷しながら、N-(3',4'-ジクロロビフェニル -2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド 0.25 g 及びヨウ化メチル 0.09 g を、N,N-ジメチルホルムアミド 5 ml 中の水素化ナトリウム 0.02 g の溶液に加えた。この混合物を室温で12時間攪拌し、次いで1%濃度の塩酸及びメチルtert-ブチルエーテルを加えた。有機相を順次に水及び飽和塩化ナトリウム水溶液で洗浄し、この溶液を減圧下に濃縮した。粗生成物をシリカゲルカラムクロマトグラフィーによりシクロヘキサン/酢酸エチル1:1を用いて精製した。これは目的生成物 0.15 g のをミルク様油状物として与えた。
N-(3',4'-ジクロロビフェニル-2-イル)-3-(ジクロロフルオロメチル)-1-メチル-1H-ピラゾール-4-カルボキサミド
a) N-(3’,4-ジクロロビフェニル-2-イル)-3-(ジクロロフルオロメチル)-1-メチル-1H-ピラゾール-4-カルボキサミド
4bからの油状物 0.37 g を、トルエン 10 ml 中の 3',4'-ジクロロ-2-アミノビフェニル 0.36 g 及びピリジン 0.18 g の溶液を滴下し、反応混合物を室温で16時間攪拌した。次いでテトラヒドロフラン 10 ml 及びメチルtert-ブチルエーテル 30 ml を加えた。有機相を順次に2%濃度の塩酸で、飽和重炭酸ナトリウム水溶液で2回及び希塩化ナトリウム水溶液で洗浄した。有機相を乾燥し、減圧下に濃縮した。粗生成物をジイソプロピルエーテル 10 ml と共に磨砕し、残った固体を吸引濾別し、乾燥した。これは目的生成物 0.48 g を融点145〜146℃の白色固体として与えた。
3-ジクロロフルオロメチル-1-メチル-4-ピラゾールカルボン酸 5.3 g 及びチオニルクロリド 27.8 g の混合物を、2時間還流加熱した。次いで回転蒸発器を用いて反応混合物を濃縮し、トルエン 50 ml と共に2回共沸した。単離した油状物を更に精製することなくそのままで更に反応させた。
室温で、テトラヒドロフラン 20 ml 中の 3-ジクロロフルオロメチル-1-メチル-4-ピラゾールカルボン酸エチル 10.20 g の溶液を、カリウムトリメチルシラノレート 5.13 g 及びテトラヒドロフラン 100 ml の混合物に滴下し、この混合物を室温で12時間攪拌した。沈殿を吸引濾別し、テトラヒドロフランで洗浄し、減圧下に乾燥した。生成した固体を氷水 200 ml に溶解し、10%濃度の塩酸を用いてこの溶液を pH2に調節した。沈殿をメチルtert-ブチルエーテルで2回抽出し、一緒にした有機相を飽和塩化ナトリウム水溶液で洗浄した。乾燥して溶剤を減圧下に蒸発させた後、上記の酸 5.50 g を融点167〜169℃の白色粉末として単離した。
本発明に係る化合物Iの殺菌作用を、下記の試験により示した。
品種 "Neusiedler Ideal Elite" のピーマンの苗に、2〜3葉が十分発育した後に、以下に記載する活性化合物濃度を有する水性懸濁液を流出点まで噴霧した。翌日、処理した植物に、2%バイオモルト水溶液中に 1.7 x 106 胞子/mlを含むボトリチス・シネレアの水性胞子懸濁液を接種した。次いで試験植物を22〜24℃及び高大気湿度の気候条件順応暗室に入れた。5日後に、葉面上の菌感染の程度は肉眼で%として決定することができた。
品種 "Kanzler" のコムギ植物の鉢に、以下に記載する活性化合物濃度を有する水性懸濁液を流出点まで噴霧した。翌日、レプトスフェリア・ノドルム(スタゴノスポラ・ノドルム、セプトロイア・ノドルム(Septoroia nodorum)と同義)の水性胞子懸濁液を接種した。次いで植物を20℃及び最高大気湿度の温室に入れた。8日後に、未処理であるが感染した対照植物における葉枯病は、感染が肉眼で%として決定できる程度まで発症した。
鉢植えした品種 "Kanzler" のコムギ苗の葉に、褐色さび病菌 (プッチニア・レコンジタ)の胞子懸濁液を接種した。次いで鉢を高大気湿度(90〜95%)及び20〜22℃の部屋に24時間入れた。この時間中に胞子が発生し、芽管が葉の組織に貫通した。翌日、感染した植物に、以下に記載する活性化合物濃度を有する水性懸濁液を流出点まで噴霧した。懸濁液又はエマルジョンは上記のように準備した。噴霧コーティングが乾燥した後、試験植物を温度20〜22℃及び相対大気湿度65〜70%の部屋で7日間栽培した。次いで葉におけるさび病菌発生の程度を決定した。
EP-A 0 589 301 からの表1の化合物 No. 47 を、表9からの本発明に係る化合物 9.17 及び9.20 と比較した。
Claims (12)
- 式Iのピラゾールカルボキシアニリド
nはゼロ又は2であり;
mは2又は3であり;
X1はフッ素又は塩素であり、ここで、n=2の場合には、二つの基X1は異なる意味を有することができ;
X2はハロゲンであり、ここで基X2は異なる意味を有することができ;
YはCN、NO2、C1-C4-アルキル、C1-C4-ハロアルキル、メトキシ又はメチルチオであり;
pはゼロ又は1であり;
R1はフッ素、塩素、臭素、C1-C4-アルキル又はC1-C4-ハロアルキルであり;
R2は水素又はハロゲンであり;
R3は水素、メチル又はエチルであり;
WはO又はSであり;
但し、
a)W=O、R1=メチル、そしてR3が水素であるならば、R2はFではなく、又は
b)W=O、n=0、m=2、p=0、R2及びR3が水素であるならば、R1はトリフルオロメチル又はジフルオロメチルではない)。 - 可変部が下記の通り定義される請求項1に記載の式Iのピラゾールカルボキシアニリド:
YはC1-C4-アルキル、C1-C4-ハロアルキル又はメトキシであり;
R3は水素又はメチルであり;
Wは酸素である。 - 可変部が下記の通り定義される請求項1及び2の何れかに記載の式Iのピラゾールカルボキシアニリド:
X2はフッ素又は塩素であり;
Yはメチル、ジフルオロメチル、トリフルオロメチル又はメトキシであり;
R1はフッ素、塩素、メチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチルであり;
R2は水素、フッ素又は塩素であり;
R3は水素又はメチルであり;
Wは酸素である。 - 可変部が下記の通り定義される請求項1〜3の何れかに記載の式Iのピラゾールカルボキシアニリド:
X2はフッ素又は塩素であり;
nはゼロであり;
pはゼロであり;
R1はフッ素、塩素、メチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチルであり;
R2は水素、フッ素又は塩素であり;
R3は水素であり;
Wは酸素である。 - 可変部が下記の通り定義される請求項1〜4の何れかに記載の式Iのピラゾールカルボキシアニリド:
X2はフッ素又は塩素であり;
nはゼロであり;
pはゼロであり;
R1はフッ素、塩素、メチル、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチルであり;
R2は水素又は塩素であり;
R3は水素であり;
Wは酸素である。 - 可変部が下記の通り定義される請求項1〜4の何れかに記載の式Iのピラゾールカルボキシアニリド:
X2はフッ素又は塩素であり;
nはゼロであり;
pはゼロであり;
R1はフッ素、塩素、フルオロメチル、ジフルオロメチル、クロロフルオロメチル、クロロジフルオロメチル、ジクロロフルオロメチル又はトリフルオロメチルであり;
R2は水素又は塩素であり;
R3は水素であり;
Wは酸素である。 - 以下の化合物からなる群から選択される請求項1に記載の式Iのピラゾールカルボキシアニリド:
N-(3',4'-ジクロロビフェニル-2-イル)-5-クロロ-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジクロロビフェニル-2-イル)-5-クロロ-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-5-クロロ-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-5-クロロ-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(4'-クロロ-2'-フルオロ-5'-メトキシビフェニル-2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(4'-クロロ-2'-フルオロ-5'-メチルビフェニル-2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',3',4'-トリフルオロビフェニル-2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(4'-クロロ-2'-フルオロ-5'-メトキシビフェニル-2-イル)-1-メチル-3-ジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(4'-クロロ-2'-フルオロ-5'-メチルビフェニル-2-イル)-1-メチル-3-ジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-ジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-ジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジクロロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジフルオロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-フルオロ-4'-クロロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジフルオロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(2'-フルオロ-4'-クロロビフェニル-2-イル)-1,3-ジメチル-1H-ピラゾール-4-カルボキサミド、
N-(3,2',4'-トリクロロ-5-フルオロビフェニル-2-イル)-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3,3',4'-トリクロロ-5-フルオロビフェニル-2-イル)-1-メチル-3-ジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3-クロロ-5,3',4'-トリフルオロビフェニル-2-イル)-1-メチル-3-ジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-1-メチル-3-クロロジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-1-メチル-3-クロロジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジフルオロビフェニル-2-イル)-1-メチル-3-クロロジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-1-メチル-3-クロロジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジクロロビフェニル-2-イル)-1-メチル-3-クロロジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-クロロジフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-5-フルオロ-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-5-フルオロ-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジクロロビフェニル-2-イル)-5-フルオロ-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-5-フルオロ-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-N-メチル-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-N-エチル-1-メチル-3-トリフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-1-メチル-3-クロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-1-メチル-3-クロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジフルオロビフェニル-2-イル)-1-メチル-3-クロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-1-メチル-3-クロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジクロロビフェニル-2-イル)-1-メチル-3-クロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-クロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジフルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジクロロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-フルオロ-4'-クロロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2'-フルオロ-4'-クロロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',3',4'-トリフルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4',5'-トリフルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2',4'-ジフルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(2'-クロロ-4'-フルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジフルオロビフェニル-2-イル)-1-メチル-3-フルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジクロロビフェニル-2-イル)-1-メチル-3-ジクロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3'-クロロ-4'-フルオロビフェニル-2-イル)-1-メチル-3-ジクロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',4'-ジフルオロビフェニル-2-イル)-1-メチル-3-ジクロロフルオロメチル-1H-ピラゾール-4-カルボキサミド、
N-(3',5'-ジクロロビフェニル-2-イル)-1-メチル-3-ジクロロフルオロメチル-1H-ピラゾール-4-カルボキサミド及び
N-(2',4'-ジクロロビフェニル-2-イル)-1-メチル-3-ジクロロフルオロメチル-1H-ピラゾール-4-カルボキサミド。 - 殺菌量の請求項1〜7の何れかに記載の式Iの化合物及び少なくとも1種の不活性添加物を含む、有害菌を防除するための組成物。
- 更なる活性化合物を追加して含む、請求項8に記載の組成物。
- 有害菌、それらの生息環境及び/又は菌の攻撃に対して保護すべき材料、植物、土壌若しくは種子を殺菌有効量の請求項1〜7の何れかに記載の式Iの化合物で処理することを含む、植物病原性有害菌の防除方法。
- 植物病原性有害菌を防除するための請求項1〜7の何れかに記載の式Iの化合物の使用。
- 請求項1〜7の何れかに記載の式Iの化合物を1〜1000g/100kg の量で含む種子。
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