JP2016522175A5 - - Google Patents
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- JP2016522175A5 JP2016522175A5 JP2016508973A JP2016508973A JP2016522175A5 JP 2016522175 A5 JP2016522175 A5 JP 2016522175A5 JP 2016508973 A JP2016508973 A JP 2016508973A JP 2016508973 A JP2016508973 A JP 2016508973A JP 2016522175 A5 JP2016522175 A5 JP 2016522175A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- halogen
- alkoxy
- independently
- 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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- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
- 244000000004 fungal plant pathogen Species 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 description 21
- 229910052731 fluorine Inorganic materials 0.000 description 21
- 229910052794 bromium Inorganic materials 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 2
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 2
- 244000301083 Ustilago maydis Species 0.000 description 2
- 235000015919 Ustilago maydis Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- BHKLQQYJTSKOEC-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-N-[1-[6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]propan-2-yl]pyrazole-4-carboxamide Chemical compound FC(C1=NN(C=C1C(=O)NC(CC=1C=NC(=CC1)N1N=C(C=C1)C(F)(F)F)C)C)F BHKLQQYJTSKOEC-UHFFFAOYSA-N 0.000 description 1
- CCGSJXHJMRRSOY-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-N-[2-[2-[3-(trifluoromethyl)pyrazol-1-yl]pyrimidin-5-yl]phenyl]pyrazole-4-carboxamide Chemical compound FC(C1=NN(C=C1C(=O)NC1=C(C=CC=C1)C=1C=NC(=NC1)N1N=C(C=C1)C(F)(F)F)C)F CCGSJXHJMRRSOY-UHFFFAOYSA-N 0.000 description 1
- XVOMXLBKMVZLTG-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-N-[2-[5-[3-(trifluoromethyl)pyrazol-1-yl]pyrazin-2-yl]phenyl]pyrazole-4-carboxamide Chemical compound FC(C1=NN(C=C1C(=O)NC1=C(C=CC=C1)C1=NC=C(N=C1)N1N=C(C=C1)C(F)(F)F)C)F XVOMXLBKMVZLTG-UHFFFAOYSA-N 0.000 description 1
- SBUBZWUDYXJSQL-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-N-[2-[6-[3-(trifluoromethyl)pyrazol-1-yl]pyridazin-3-yl]phenyl]pyrazole-4-carboxamide Chemical compound FC(C1=NN(C=C1C(=O)NC1=C(C=CC=C1)C=1N=NC(=CC1)N1N=C(C=C1)C(F)(F)F)C)F SBUBZWUDYXJSQL-UHFFFAOYSA-N 0.000 description 1
- CVAPYIHQKPOFIP-UHFFFAOYSA-N 3-(difluoromethyl)-1-methyl-N-[2-[6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]pyrazole-4-carboxamide Chemical compound CN1C=C(C(=O)NC2=C(C=CC=C2)C2=CC=C(N=C2)N2C=CC(=N2)C(F)(F)F)C(=N1)C(F)F CVAPYIHQKPOFIP-UHFFFAOYSA-N 0.000 description 1
- PNJLLQCXVKMZSV-UHFFFAOYSA-N 3-(difluoromethyl)-N-[2-[5-fluoro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-1-methylpyrazole-4-carboxamide Chemical compound FC(C1=NN(C=C1C(=O)NC1=C(C=CC=C1)C=1C=NC(=C(C1)F)N1N=C(C=C1)C(F)(F)F)C)F PNJLLQCXVKMZSV-UHFFFAOYSA-N 0.000 description 1
- MTXDWGLUSPFESG-UHFFFAOYSA-N 3-(trifluoromethyl)-N-[2-[2-[3-(trifluoromethyl)pyrazol-1-yl]pyrimidin-5-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(C=1C(=NC=CC1)C(=O)NC1=C(C=CC=C1)C=1C=NC(=NC1)N1N=C(C=C1)C(F)(F)F)(F)F MTXDWGLUSPFESG-UHFFFAOYSA-N 0.000 description 1
- IFMFQJUBZLDPCZ-UHFFFAOYSA-N 3-bromo-N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1=NN(C=C1)C1=C(Cl)C=C(C=N1)C1=C(NC(=O)C2=NC=CC=C2Br)C=CC=C1 IFMFQJUBZLDPCZ-UHFFFAOYSA-N 0.000 description 1
- HORGLJWYZPAAAR-UHFFFAOYSA-N 3-bromo-N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=NN(C=C1)C1=C(Cl)C=C(C=N1)C1=C(NC(=O)C2=C(Br)C=CS2)C=CC=C1 HORGLJWYZPAAAR-UHFFFAOYSA-N 0.000 description 1
- FTORCGRNVOEHNL-UHFFFAOYSA-N 5-bromo-N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-1,3-thiazole-4-carboxamide Chemical compound FC(F)(F)C1=NN(C=C1)C1=C(Cl)C=C(C=N1)C1=C(NC(=O)C2=C(Br)SC=N2)C=CC=C1 FTORCGRNVOEHNL-UHFFFAOYSA-N 0.000 description 1
- 241000223602 Alternaria alternata Species 0.000 description 1
- 240000006439 Aspergillus oryzae Species 0.000 description 1
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000493670 Botrytis elliptica Species 0.000 description 1
- 241000609455 Corynespora cassiicola Species 0.000 description 1
- 229940124186 Dehydrogenase inhibitor Drugs 0.000 description 1
- HAKAMRMMRAGSGR-UHFFFAOYSA-N N-[2-(5-chloro-6-pyrazol-1-ylpyridin-3-yl)phenyl]-3-(trifluoromethyl)pyridine-2-carboxamide Chemical compound ClC=1C=C(C=NC1N1N=CC=C1)C1=C(C=CC=C1)NC(=O)C1=NC=CC=C1C(F)(F)F HAKAMRMMRAGSGR-UHFFFAOYSA-N 0.000 description 1
- NVJPSBXUPSJNSC-UHFFFAOYSA-N N-[2-[5-chloro-6-(4-chloropyrazol-1-yl)pyridin-3-yl]phenyl]-3-(trifluoromethyl)pyridine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CN=C1C(=O)NC1=C(C=CC=C1)C1=CC(Cl)=C(N=C1)N1C=C(Cl)C=N1 NVJPSBXUPSJNSC-UHFFFAOYSA-N 0.000 description 1
- QKBIDTPVRNOFQZ-UHFFFAOYSA-N N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-3-(trifluoromethyl)pyridine-2-carboxamide Chemical compound ClC=1C=C(C=NC1N1N=C(C=C1)C(F)(F)F)C1=C(C=CC=C1)NC(=O)C1=NC=CC=C1C(F)(F)F QKBIDTPVRNOFQZ-UHFFFAOYSA-N 0.000 description 1
- JOWIQFCERAVNFT-UHFFFAOYSA-N N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-3-iodopyridine-2-carboxamide Chemical compound ClC=1C=C(C=NC1N1N=C(C=C1)C(F)(F)F)C1=C(C=CC=C1)NC(=O)C1=NC=CC=C1I JOWIQFCERAVNFT-UHFFFAOYSA-N 0.000 description 1
- JWNNRANEHFJIFI-UHFFFAOYSA-N N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-3-iodothiophene-2-carboxamide Chemical compound ClC=1C=C(C=NC1N1N=C(C=C1)C(F)(F)F)C1=C(C=CC=C1)NC(=O)C=1SC=CC1I JWNNRANEHFJIFI-UHFFFAOYSA-N 0.000 description 1
- DKNHWXZXYWKNFZ-UHFFFAOYSA-N N-[2-[5-chloro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-5-iodo-1,3-thiazole-4-carboxamide Chemical compound ClC=1C=C(C=NC1N1N=C(C=C1)C(F)(F)F)C1=C(C=CC=C1)NC(=O)C=1N=CSC1I DKNHWXZXYWKNFZ-UHFFFAOYSA-N 0.000 description 1
- BEJZNHNMEYTQBC-UHFFFAOYSA-N N-[2-[5-fluoro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-3-iodothiophene-2-carboxamide Chemical compound FC=1C=C(C=NC1N1N=C(C=C1)C(F)(F)F)C1=C(C=CC=C1)NC(=O)C=1SC=CC1I BEJZNHNMEYTQBC-UHFFFAOYSA-N 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 241000371621 Stemphylium Species 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WAJUOEZCXDCRPI-UHFFFAOYSA-N n-[2-[5-fluoro-6-[3-(trifluoromethyl)pyrazol-1-yl]pyridin-3-yl]phenyl]-3-(trifluoromethyl)pyridine-2-carboxamide Chemical compound FC1=CC(C=2C(=CC=CC=2)NC(=O)C=2C(=CC=CN=2)C(F)(F)F)=CN=C1N1C=CC(C(F)(F)F)=N1 WAJUOEZCXDCRPI-UHFFFAOYSA-N 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361811907P | 2013-04-15 | 2013-04-15 | |
| US61/811,907 | 2013-04-15 | ||
| PCT/US2014/033752 WO2014172190A1 (en) | 2013-04-15 | 2014-04-11 | Fungicidal amides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016522175A JP2016522175A (ja) | 2016-07-28 |
| JP2016522175A5 true JP2016522175A5 (https=) | 2017-04-13 |
| JP6419783B2 JP6419783B2 (ja) | 2018-11-07 |
Family
ID=50680207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016508973A Expired - Fee Related JP6419783B2 (ja) | 2013-04-15 | 2014-04-11 | 殺菌・殺カビ性アミド |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9730447B2 (https=) |
| EP (1) | EP2986594B1 (https=) |
| JP (1) | JP6419783B2 (https=) |
| KR (1) | KR102227271B1 (https=) |
| CN (1) | CN105121411B (https=) |
| AR (1) | AR096023A1 (https=) |
| AU (1) | AU2014254261B2 (https=) |
| BR (1) | BR112015025686B1 (https=) |
| CL (1) | CL2015003006A1 (https=) |
| MX (1) | MX374634B (https=) |
| PL (1) | PL2986594T3 (https=) |
| WO (1) | WO2014172190A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10098350B2 (en) | 2013-04-15 | 2018-10-16 | E. I. Du Pont De Nemours And Company | Fungicidal amides |
| WO2016094307A1 (en) | 2014-12-08 | 2016-06-16 | The Research Foundation For The State University Of New York | Anti-fungals targeting the synthesis of fungal shingolipids |
| CN107531676A (zh) | 2015-04-13 | 2018-01-02 | 拜耳作物科学股份公司 | N‑环烷基‑n‑(双杂环基亚乙基)‑(硫代)羧酰胺衍生物 |
| WO2018232298A1 (en) | 2017-06-16 | 2018-12-20 | The Research Foundation For The State University Of New York | Anti-fungals compounds targeting the synthesis of fungal sphingolipids |
| CN110878086B (zh) * | 2018-09-06 | 2024-06-07 | 青岛清原化合物有限公司 | 五元环取代的哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 |
| US12024500B2 (en) * | 2018-02-02 | 2024-07-02 | Qingdao Kingagroot Chemical Compound Co., Ltd. | Five-membered ring-substituted pyridazinol compounds and derivatives, preparation methods, herbicidal compositions and applications thereof |
| WO2019148850A1 (zh) | 2018-02-02 | 2019-08-08 | 青岛清原化合物有限公司 | 吡啶环取代的哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 |
| CN110857452A (zh) * | 2018-08-23 | 2020-03-03 | 中国农业科学院蔬菜花卉研究所 | 一种检测SdhB-H278R点突变的含量的方法及其专用成套试剂 |
| TWI819078B (zh) * | 2018-09-06 | 2023-10-21 | 美商富曼西公司 | 殺真菌之經硝苯胺基取代之吡唑 |
| TWI853009B (zh) | 2019-03-29 | 2024-08-21 | 瑞士商先正達農作物保護公司 | 殺有害生物活性之二-醯胺化合物 |
| CN110122495A (zh) * | 2019-06-14 | 2019-08-16 | 马毅辉 | 含有1-(3-氯-2-吡啶基)-1氢-吡唑活性片段的化合物在制备杀菌剂中的应用 |
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-
2014
- 2014-04-11 BR BR112015025686-4A patent/BR112015025686B1/pt not_active IP Right Cessation
- 2014-04-11 MX MX2015014407A patent/MX374634B/es active IP Right Grant
- 2014-04-11 WO PCT/US2014/033752 patent/WO2014172190A1/en not_active Ceased
- 2014-04-11 US US14/783,622 patent/US9730447B2/en not_active Expired - Fee Related
- 2014-04-11 AU AU2014254261A patent/AU2014254261B2/en not_active Ceased
- 2014-04-11 PL PL14722505T patent/PL2986594T3/pl unknown
- 2014-04-11 KR KR1020157032287A patent/KR102227271B1/ko not_active Expired - Fee Related
- 2014-04-11 JP JP2016508973A patent/JP6419783B2/ja not_active Expired - Fee Related
- 2014-04-11 EP EP14722505.6A patent/EP2986594B1/en not_active Not-in-force
- 2014-04-11 CN CN201480021370.1A patent/CN105121411B/zh not_active Expired - Fee Related
- 2014-04-14 AR ARP140101582A patent/AR096023A1/es active IP Right Grant
-
2015
- 2015-10-09 CL CL2015003006A patent/CL2015003006A1/es unknown
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