JP2018515548A5 - - Google Patents
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- Publication number
- JP2018515548A5 JP2018515548A5 JP2017559830A JP2017559830A JP2018515548A5 JP 2018515548 A5 JP2018515548 A5 JP 2018515548A5 JP 2017559830 A JP2017559830 A JP 2017559830A JP 2017559830 A JP2017559830 A JP 2017559830A JP 2018515548 A5 JP2018515548 A5 JP 2018515548A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- methyl
- cyclopropyl
- compound
- difluoromethyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 43
- 241000207199 Citrus Species 0.000 claims 12
- 235000020971 citrus fruits Nutrition 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 241000196324 Embryophyta Species 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 241000234295 Musa Species 0.000 claims 6
- 235000018290 Musa x paradisiaca Nutrition 0.000 claims 6
- 206010039509 Scab Diseases 0.000 claims 6
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 6
- 241000894007 species Species 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims 4
- 229940126062 Compound A Drugs 0.000 claims 4
- 241001181537 Hemileia Species 0.000 claims 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 4
- 208000031888 Mycoses Diseases 0.000 claims 4
- 206010000496 acne Diseases 0.000 claims 4
- -1 2-cyclopropyl Chemical group 0.000 claims 3
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 claims 2
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 claims 2
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 241000125117 Elsinoe Species 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 206010018612 Gonorrhoea Diseases 0.000 claims 2
- 241000555714 Phyllosticta citricarpa Species 0.000 claims 2
- 241000087479 Pseudocercospora fijiensis Species 0.000 claims 2
- 208000001786 gonorrhea Diseases 0.000 claims 2
- YGGNKXSVYCKXCA-UHFFFAOYSA-N n-[(2-cyclopentyl-5-fluorophenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=C(F)C=2)C2CCCC2)C2CC2)=C1F YGGNKXSVYCKXCA-UHFFFAOYSA-N 0.000 claims 2
- ACDCNNFPJPHJCQ-UHFFFAOYSA-N n-[(2-tert-butyl-5-methylphenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CC1=CC=C(C(C)(C)C)C(CN(C2CC2)C(=O)C=2C(=NN(C)C=2F)C(F)F)=C1 ACDCNNFPJPHJCQ-UHFFFAOYSA-N 0.000 claims 2
- PZSVWPHTFIJDAX-UHFFFAOYSA-N n-[(2-tert-butylphenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=CC=2)C(C)(C)C)C2CC2)=C1F PZSVWPHTFIJDAX-UHFFFAOYSA-N 0.000 claims 2
- ZNPUHPIMSDMYGC-UHFFFAOYSA-N n-[(5-chloro-2-ethylphenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CCC1=CC=C(Cl)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 ZNPUHPIMSDMYGC-UHFFFAOYSA-N 0.000 claims 2
- JEFUQUGZXLEHLD-UHFFFAOYSA-N n-[(5-chloro-2-propan-2-ylphenyl)methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1=CC=C(Cl)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 JEFUQUGZXLEHLD-UHFFFAOYSA-N 0.000 claims 2
- UTXLNSPIBIMGQJ-UHFFFAOYSA-N n-[[2-chloro-6-(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=CC=2Cl)C(F)(F)F)C2CC2)=C1F UTXLNSPIBIMGQJ-UHFFFAOYSA-N 0.000 claims 2
- POIXHZKAAMCWOT-UHFFFAOYSA-N n-[[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=C(Cl)C=2F)C(F)(F)F)C2CC2)=C1F POIXHZKAAMCWOT-UHFFFAOYSA-N 0.000 claims 2
- HEMPTJWLSOMNER-UHFFFAOYSA-N n-[[5-chloro-2-(trifluoromethyl)phenyl]methyl]-n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=C(Cl)C=2)C(F)(F)F)C2CC2)=C1F HEMPTJWLSOMNER-UHFFFAOYSA-N 0.000 claims 2
- YSVBFKLFADDJEI-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-n-[(2-propan-2-ylphenyl)methyl]pyrazole-4-carbothioamide Chemical compound CC(C)C1=CC=CC=C1CN(C(=S)C=1C(=NN(C)C=1F)C(F)F)C1CC1 YSVBFKLFADDJEI-UHFFFAOYSA-N 0.000 claims 2
- YBQARPUVLHEOSY-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-n-[(2-propan-2-ylphenyl)methyl]pyrazole-4-carboxamide Chemical compound CC(C)C1=CC=CC=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 YBQARPUVLHEOSY-UHFFFAOYSA-N 0.000 claims 2
- MRCJJCNYJGXHAU-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-n-[(5-methyl-2-propan-2-ylphenyl)methyl]pyrazole-4-carboxamide Chemical compound CC(C)C1=CC=C(C)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 MRCJJCNYJGXHAU-UHFFFAOYSA-N 0.000 claims 2
- GZSDSDAVLHAHBW-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-n-[[5-methyl-2-(trifluoromethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound CC1=CC=C(C(F)(F)F)C(CN(C2CC2)C(=O)C=2C(=NN(C)C=2F)C(F)F)=C1 GZSDSDAVLHAHBW-UHFFFAOYSA-N 0.000 claims 2
- YBQVYCCAGISJDK-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-n-[(2-fluoro-6-propan-2-ylphenyl)methyl]-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1=CC=CC(F)=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 YBQVYCCAGISJDK-UHFFFAOYSA-N 0.000 claims 2
- KBWODRLEGDCUHW-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-5-fluoro-n-[(5-fluoro-2-propan-2-ylphenyl)methyl]-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1=CC=C(F)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 KBWODRLEGDCUHW-UHFFFAOYSA-N 0.000 claims 2
- FLQNESNIAKFCNJ-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-n-[(2-ethyl-4,5-dimethylphenyl)methyl]-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CCC1=CC(C)=C(C)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 FLQNESNIAKFCNJ-UHFFFAOYSA-N 0.000 claims 2
- QXZWXYMHKYWUJC-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-n-[(2-ethyl-5-fluorophenyl)methyl]-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CCC1=CC=C(F)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 QXZWXYMHKYWUJC-UHFFFAOYSA-N 0.000 claims 2
- GVRURMVTCDBWMT-UHFFFAOYSA-N n-cyclopropyl-3-(difluoromethyl)-n-[(2-ethyl-5-methylphenyl)methyl]-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CCC1=CC=C(C)C=C1CN(C(=O)C=1C(=NN(C)C=1F)C(F)F)C1CC1 GVRURMVTCDBWMT-UHFFFAOYSA-N 0.000 claims 2
- PBBIVBOBRLKLGM-UHFFFAOYSA-N n-cyclopropyl-n-[(2-cyclopropyl-5-fluorophenyl)methyl]-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=C(F)C=2)C2CC2)C2CC2)=C1F PBBIVBOBRLKLGM-UHFFFAOYSA-N 0.000 claims 2
- ZDVWJXRWGQXPIA-UHFFFAOYSA-N n-cyclopropyl-n-[(2-cyclopropyl-5-methylphenyl)methyl]-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound C1CC1N(C(=O)C=1C(=NN(C)C=1F)C(F)F)CC1=CC(C)=CC=C1C1CC1 ZDVWJXRWGQXPIA-UHFFFAOYSA-N 0.000 claims 2
- XTRVHRSUSXRHLB-UHFFFAOYSA-N n-cyclopropyl-n-[(2-cyclopropylphenyl)methyl]-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide Chemical compound CN1N=C(C(F)F)C(C(=O)N(CC=2C(=CC=CC=2)C2CC2)C2CC2)=C1F XTRVHRSUSXRHLB-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 claims 1
- 239000000642 acaricide Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 239000005667 attractant Substances 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 239000003337 fertilizer Substances 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 239000003630 growth substance Substances 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000005645 nematicide Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15290131 | 2015-05-19 | ||
| EP15290131.0 | 2015-05-19 | ||
| PCT/EP2016/061064 WO2016184879A1 (en) | 2015-05-19 | 2016-05-18 | Method for treating coffee rust, citrus black spot, citrus scab and banana black sigatoka diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018515548A JP2018515548A (ja) | 2018-06-14 |
| JP2018515548A5 true JP2018515548A5 (enExample) | 2019-01-17 |
| JP6633653B2 JP6633653B2 (ja) | 2020-01-22 |
Family
ID=53268746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017559830A Expired - Fee Related JP6633653B2 (ja) | 2015-05-19 | 2016-05-18 | コーヒーさび病、カンキツ類黒星病、カンキツ類瘡痂病およびバナナブラックシガトカ病の治療方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10349658B2 (enExample) |
| EP (1) | EP3297439B1 (enExample) |
| JP (1) | JP6633653B2 (enExample) |
| KR (1) | KR20180008703A (enExample) |
| CN (1) | CN107635403B (enExample) |
| AR (1) | AR104687A1 (enExample) |
| BR (1) | BR112017024741B1 (enExample) |
| ES (1) | ES2786278T3 (enExample) |
| MX (1) | MX395394B (enExample) |
| PH (1) | PH12017502069A1 (enExample) |
| WO (1) | WO2016184879A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR104687A1 (es) * | 2015-05-19 | 2017-08-09 | Bayer Cropscience Ag | Método para tratar las enfermedades roya del café, mancha negra de los cítricos, sarna de los cítricos y sigatoka negra de la banana |
| US11319553B2 (en) | 2017-11-29 | 2022-05-03 | Rahan Meristem (1998) Ltd. | Compositions and methods conferring resistance to fungal diseases |
| JP2022136336A (ja) * | 2019-08-21 | 2022-09-16 | 日産化学株式会社 | シガトカ病の防除方法 |
| US20220354118A1 (en) * | 2019-10-02 | 2022-11-10 | Syngenta Crop Protection Ag | Methods of controlling or preventing infestation of banana plants by phytopathogenic microorganisms of the genus pseudocercospora |
| CN110915512B (zh) * | 2019-10-28 | 2021-07-27 | 江西环境工程职业学院 | 一种丝栗栲高效抑菌控根的育苗方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005035300A1 (de) * | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| AR056882A1 (es) | 2006-02-01 | 2007-10-31 | Bayer Cropscience Sa | Derivados del fungicida n- cicloalquil- bencil- amida |
| EP2004194B1 (en) * | 2006-03-31 | 2016-04-27 | Syngenta Participations AG | Azoxystrobin formulations |
| CA2692767C (en) | 2007-07-31 | 2016-02-09 | Bayer Cropscience Sa | Fungicidal n-cycloalkyl-benzyl-thiocarboxamides or n-cycloalkyl-benzyl-n'-substituted-amidine derivatives |
| AU2009250299A1 (en) | 2008-05-22 | 2009-11-26 | Merck Frosst Canada Ltd | 3, 4 - substituted piperidine derivatives as renin inhibitors |
| EP2251331A1 (en) * | 2009-05-15 | 2010-11-17 | Bayer CropScience AG | Fungicide pyrazole carboxamides derivatives |
| AR076839A1 (es) * | 2009-05-15 | 2011-07-13 | Bayer Cropscience Ag | Derivados fungicidas de pirazol carboxamidas |
| EA029682B1 (ru) * | 2011-04-22 | 2018-04-30 | Байер Интеллекчуал Проперти Гмбх | Комбинации активных соединений, содержащие производное соединение (тио)карбоксамида и фунгицидное соединение |
| JPWO2013141362A1 (ja) * | 2012-03-23 | 2015-08-03 | 日本農薬株式会社 | チアゾールカルボキサミド誘導体及びその使用方法 |
| UA114648C2 (uk) * | 2012-10-19 | 2017-07-10 | Байєр Кропсайнс Аг | Спосіб обробки рослин проти грибів, стійких до фунгіцидів, із застосуванням карбоксамідних або тіокарбоксамідних похідних |
| EA026839B1 (ru) * | 2012-10-19 | 2017-05-31 | Байер Кропсайенс Аг | Комбинации активных соединений, содержащие карбоксамидные соединения |
| EA026742B1 (ru) * | 2012-10-19 | 2017-05-31 | Байер Кропсайенс Аг | Комбинации активного соединения, содержащие производные карбоксамида и агент биологического контроля |
| JP2014224067A (ja) * | 2013-05-16 | 2014-12-04 | 日本農薬株式会社 | 農園芸用殺菌剤組成物及びその使用方法 |
| WO2015055707A1 (en) * | 2013-10-16 | 2015-04-23 | Bayer Cropscience Ag | Active compound combinations comprising a (thio)carboxamide derivative and a fungicidal compound |
| AR102987A1 (es) * | 2014-12-16 | 2017-04-05 | Bayer Cropscience Ag | Combinaciones de compuestos activos que comprenden un derivado de (tio)carboxamida y compuesto(s) fungicida(s) |
| AR104687A1 (es) * | 2015-05-19 | 2017-08-09 | Bayer Cropscience Ag | Método para tratar las enfermedades roya del café, mancha negra de los cítricos, sarna de los cítricos y sigatoka negra de la banana |
| TWI782983B (zh) * | 2017-04-27 | 2022-11-11 | 德商拜耳廠股份有限公司 | 雜芳基苯基胺基喹啉及類似物 |
-
2016
- 2016-05-17 AR ARP160101444A patent/AR104687A1/es unknown
- 2016-05-18 CN CN201680028772.3A patent/CN107635403B/zh not_active Expired - Fee Related
- 2016-05-18 US US15/575,298 patent/US10349658B2/en active Active
- 2016-05-18 BR BR112017024741-0A patent/BR112017024741B1/pt active IP Right Grant
- 2016-05-18 ES ES16723124T patent/ES2786278T3/es active Active
- 2016-05-18 KR KR1020177036245A patent/KR20180008703A/ko not_active Abandoned
- 2016-05-18 EP EP16723124.0A patent/EP3297439B1/en active Active
- 2016-05-18 WO PCT/EP2016/061064 patent/WO2016184879A1/en not_active Ceased
- 2016-05-18 MX MX2017014830A patent/MX395394B/es unknown
- 2016-05-18 JP JP2017559830A patent/JP6633653B2/ja not_active Expired - Fee Related
-
2017
- 2017-11-10 PH PH12017502069A patent/PH12017502069A1/en unknown
-
2019
- 2019-06-04 US US16/431,509 patent/US10945433B2/en active Active
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