JPWO2021060240A5 - - Google Patents
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- JPWO2021060240A5 JPWO2021060240A5 JP2021548911A JP2021548911A JPWO2021060240A5 JP WO2021060240 A5 JPWO2021060240 A5 JP WO2021060240A5 JP 2021548911 A JP2021548911 A JP 2021548911A JP 2021548911 A JP2021548911 A JP 2021548911A JP WO2021060240 A5 JPWO2021060240 A5 JP WO2021060240A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- represented
- compound
- 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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- 150000001875 compounds Chemical class 0.000 claims description 64
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- -1 ( 1,3-dioxoisoindolin-2-yl)oxy group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 239000004009 herbicide Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000004292 cyclic ethers Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 244000045561 useful plants Species 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000202758 Scirpus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- GVUZCOGDXLVTAI-UHFFFAOYSA-N FC(C=1C=CC(=C2CCCSC12)B(O)O)(F)F Chemical compound FC(C=1C=CC(=C2CCCSC12)B(O)O)(F)F GVUZCOGDXLVTAI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 240000000178 Monochoria vaginalis Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- RRZYEPKJGUQWMS-UHFFFAOYSA-N 2-(azetidin-1-yl)-2-oxoacetamide Chemical group NC(=O)C(=O)N1CCC1 RRZYEPKJGUQWMS-UHFFFAOYSA-N 0.000 description 1
- JDMRFDWFEXSMSN-UHFFFAOYSA-N 2-oxo-2-pyrrolidin-1-ylacetamide Chemical group NC(=O)C(=O)N1CCCC1 JDMRFDWFEXSMSN-UHFFFAOYSA-N 0.000 description 1
- SHBSESXHPZTKTE-UHFFFAOYSA-N 5-chloro-4-methoxy-2-methylpyridazin-3-one Chemical compound COC1=C(Cl)C=NN(C)C1=O SHBSESXHPZTKTE-UHFFFAOYSA-N 0.000 description 1
- 241000209514 Alismataceae Species 0.000 description 1
- WXLVSNKYSGQQGA-UHFFFAOYSA-N CN1C(=O)C(=C(C=N1)C2=C3CCCS(=O)(=O)C3=C(C=C2)C(F)(F)F)OC Chemical compound CN1C(=O)C(=C(C=N1)C2=C3CCCS(=O)(=O)C3=C(C=C2)C(F)(F)F)OC WXLVSNKYSGQQGA-UHFFFAOYSA-N 0.000 description 1
- 241000234646 Cyperaceae Species 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 240000002358 Echinochloa oryzoides Species 0.000 description 1
- 241000202829 Eleocharis Species 0.000 description 1
- 241000759118 Eleocharis kuroguwai Species 0.000 description 1
- 241001494496 Leersia Species 0.000 description 1
- 241001136896 Leersia japonica Species 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 241000169076 Monochoria korsakowii Species 0.000 description 1
- LWLSVNFEVKJDBZ-UHFFFAOYSA-N N-[4-(trifluoromethoxy)phenyl]-4-[[3-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]methyl]piperidine-1-carboxamide Chemical compound FC(OC1=CC=C(C=C1)NC(=O)N1CCC(CC1)CC1=CC(=CC=C1)OC1=NC=C(C=C1)C(F)(F)F)(F)F LWLSVNFEVKJDBZ-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241001330453 Paspalum Species 0.000 description 1
- 241000173219 Paspalum distichum Species 0.000 description 1
- 241000757039 Pontederiaceae Species 0.000 description 1
- 241001408202 Sagittaria pygmaea Species 0.000 description 1
- 240000009132 Sagittaria sagittifolia Species 0.000 description 1
- 244000018694 Sagittaria sinensis Species 0.000 description 1
- 235000015909 Sagittaria sinensis Nutrition 0.000 description 1
- 241000477846 Schoenoplectiella Species 0.000 description 1
- 241000759139 Schoenoplectiella hotarui Species 0.000 description 1
- 244000139819 Schoenoplectus juncoides Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005596 alkyl carboxamido group Chemical group 0.000 description 1
- PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical group NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002346 iodo group Chemical group I* 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
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical group CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical group NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical group NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 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
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019174531 | 2019-09-25 | ||
| JP2019174531 | 2019-09-25 | ||
| PCT/JP2020/035689 WO2021060240A1 (ja) | 2019-09-25 | 2020-09-23 | ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2021060240A1 JPWO2021060240A1 (https=) | 2021-04-01 |
| JPWO2021060240A5 true JPWO2021060240A5 (https=) | 2023-03-27 |
| JP7459122B2 JP7459122B2 (ja) | 2024-04-01 |
Family
ID=75165833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021548911A Active JP7459122B2 (ja) | 2019-09-25 | 2020-09-23 | ７－オキサ－３，４－ジアザビシクロ［４．１．０］ヘプタ－４－エン－２－オン化合物および除草剤 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20220289758A1 (https=) |
| EP (1) | EP4035528B1 (https=) |
| JP (1) | JP7459122B2 (https=) |
| KR (1) | KR20220066885A (https=) |
| CN (1) | CN114375292A (https=) |
| AU (1) | AU2020355994A1 (https=) |
| BR (1) | BR112022003616A2 (https=) |
| CA (1) | CA3153862A1 (https=) |
| DK (1) | DK4035528T3 (https=) |
| ES (1) | ES2984558T3 (https=) |
| HU (1) | HUE067748T2 (https=) |
| MX (1) | MX2022002898A (https=) |
| PL (1) | PL4035528T3 (https=) |
| PT (1) | PT4035528T (https=) |
| TW (1) | TWI838583B (https=) |
| UA (1) | UA128513C2 (https=) |
| WO (1) | WO2021060240A1 (https=) |
| ZA (1) | ZA202202626B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR124943A1 (es) * | 2021-03-19 | 2023-05-24 | Nippon Soda Co | Compuesto 7-oxa-3,4-diazabiciclo[4.1.0]hept-4-en-2-ona y herbicida |
| AR125081A1 (es) * | 2021-03-22 | 2023-06-07 | Nippon Soda Co | Composición herbicida |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR970008312B1 (ko) * | 1992-12-04 | 1997-05-23 | 미쓰이도오아쓰가가쿠 가부시키가이샤 | 3-아자비시클로[3.1.0]헥산-2-온 유도체와 제초제 활성 성분으로 이를 포함하는 제초제 조성물 |
| GB201117019D0 (en) | 2011-10-04 | 2011-11-16 | Syngenta Ltd | Herbicidal compounds |
| AR100448A1 (es) * | 2014-05-21 | 2016-10-05 | Bayer Cropscience Ag | 5-(hetero)aril-piridazinonas y su uso como herbicida |
| KR102354068B1 (ko) * | 2016-03-30 | 2022-01-25 | 이시하라 산교 가부시끼가이샤 | 피리다지논계 화합물 또는 그의 염, 및 그것들을 함유하는 제초제 |
| TWI785022B (zh) * | 2017-03-28 | 2022-12-01 | 美商富曼西公司 | 新穎噠嗪酮類除草劑 |
| JP7109957B2 (ja) | 2018-03-27 | 2022-08-01 | 株式会社ジャパンディスプレイ | 表示装置 |
| AR124943A1 (es) * | 2021-03-19 | 2023-05-24 | Nippon Soda Co | Compuesto 7-oxa-3,4-diazabiciclo[4.1.0]hept-4-en-2-ona y herbicida |
| AR125081A1 (es) * | 2021-03-22 | 2023-06-07 | Nippon Soda Co | Composición herbicida |
-
2020
- 2020-09-23 JP JP2021548911A patent/JP7459122B2/ja active Active
- 2020-09-23 KR KR1020227007865A patent/KR20220066885A/ko not_active Ceased
- 2020-09-23 DK DK20870221.7T patent/DK4035528T3/da active
- 2020-09-23 CA CA3153862A patent/CA3153862A1/en active Pending
- 2020-09-23 HU HUE20870221A patent/HUE067748T2/hu unknown
- 2020-09-23 MX MX2022002898A patent/MX2022002898A/es unknown
- 2020-09-23 WO PCT/JP2020/035689 patent/WO2021060240A1/ja not_active Ceased
- 2020-09-23 US US17/636,710 patent/US20220289758A1/en not_active Abandoned
- 2020-09-23 PL PL20870221.7T patent/PL4035528T3/pl unknown
- 2020-09-23 UA UAA202200941A patent/UA128513C2/uk unknown
- 2020-09-23 CN CN202080063624.1A patent/CN114375292A/zh active Pending
- 2020-09-23 PT PT208702217T patent/PT4035528T/pt unknown
- 2020-09-23 AU AU2020355994A patent/AU2020355994A1/en not_active Abandoned
- 2020-09-23 TW TW109132966A patent/TWI838583B/zh active
- 2020-09-23 BR BR112022003616A patent/BR112022003616A2/pt not_active Application Discontinuation
- 2020-09-23 ES ES20870221T patent/ES2984558T3/es active Active
- 2020-09-23 EP EP20870221.7A patent/EP4035528B1/en active Active
-
2022
- 2022-03-03 ZA ZA2022/02626A patent/ZA202202626B/en unknown
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