Title:
AZETIDINONE DERIVATIVE AND HERBICIDE CONTAINING SAME AS ACTIVE INGREDIENT
Document Type and Number:
WIPO Patent Application WO/2022/107724
Kind Code:
A1
Abstract:
The present invention provides: a novel azetidinone derivative having excellent herbicidal activity, or a salt thereof; an herbicide containing the same as an active ingredient; and a production intermediate. Provided are: an azetidinone derivative represented by general formula [I] [in the formula, Q1 represents a C3-C6 cycloalkyl group which is unsubstituted, or mono- or poly-substituted with a substituent selected from a substituent group α, a phenyl group which is unsubstituted, or mono- or poly-substituted with a substituent selected from the substituent group α, or the like, Q2 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, or the like, Y1 and Y2 each independently represent an oxygen atom or a sulfur atom, R1 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or the like, R2 and R4 each independently represent a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, R3 represents a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, or the like, the substituent group α represents a halogen atom, a nitro group, a cyano group, or the like, and a substituent group β represents a halogen atom, a nitro group, a cyano group, or the like] or a salt thereof; and an herbicide characterized by containing the same as an active ingredient.
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Inventors:
OGAWA YUTAKA (JP)
ISHIKAWA RYO (JP)
SATO TAKU (JP)
TANI MIZUHO (JP)
ISHIKAWA RYO (JP)
SATO TAKU (JP)
TANI MIZUHO (JP)
Application Number:
PCT/JP2021/041945
Publication Date:
May 27, 2022
Filing Date:
November 15, 2021
Export Citation:
Assignee:
KUMIAI CHEMICAL INDUSTRY CO (JP)
International Classes:
C07D401/04; A01N43/40; A01N43/44; A01N43/50; A01N43/54; A01N43/56; A01N43/58; A01N43/653; A01N43/713; A01N43/78; A01N43/80; A01N43/824; A01N47/02; A01N47/04; A01P13/00; C07D205/06; C07D205/08; C07D401/12; C07D401/14; C07D403/04; C07D403/10; C07D403/12; C07D403/14; C07D405/04; C07D405/10; C07D405/12; C07D405/14; C07D409/04; C07D409/12; C07D411/12; C07D413/12; C07D417/12
Foreign References:
| CN112939835A | 2021-06-11 |
Other References:
BILODEAU DIDIER A., MARGISON KAITLYN D., AHMED NOREEN, STRMISKOVA MIROSLAVA, SHERRATT ALLISON R., PEZACKI JOHN PAUL: "Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications", CHEMICAL COMMUNICATIONS, vol. 56, no. 13, 10 January 2020 (2020-01-10), UK , pages 1988 - 1991, XP055931829, ISSN: 1359-7345, DOI: 10.1039/C9CC09473C
ZAKASZEWSKA ANNA, NAJDA-MOCARSKA EWELINA, MAKOWIEC SŁAWOMIR: "Preparation of bicyclic b-lactam and bicyclic 1,3-oxazinone scaffolds using combined cycloaddition and metathesis processes", SYNTHETIC COMMUNICATIONS, vol. 48, no. 14, 18 July 2018 (2018-07-18), US , pages 1793 - 1804, XP055931833, ISSN: 0039-7911, DOI: 10.1080/00397911.2018.1465980
ZAKASZEWSKA ANNA, NAJDA-MOCARSKA EWELINA, MAKOWIEC SŁAWOMIR: "A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties", NEW JOURNAL OF CHEMISTRY, vol. 41, no. 6, 15 February 2017 (2017-02-15), GB , pages 2479 - 2489, XP055931844, ISSN: 1144-0546, DOI: 10.1039/C7NJ00445A
ALCAIDE BENITO, ALMENDROS PEDRO, ARAGONCILLO CRISTINA, CALLEJO RICARDO, RUIZ M. PILAR: "Organocatalyzed Three-Component Ugi and Passerini Reactions of 4-Oxoazetidine-2-carbaldehydes and Azetidine-2,3-diones. Application to the Synthesis of γ-Lactams and γ-Lactones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 20, 18 October 2013 (2013-10-18), pages 10154 - 10165, XP055931847, ISSN: 0022-3263, DOI: 10.1021/jo4015358
HENGZHEN QI, XINYAO LI, JIAXI XU: "Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: experimental investigation and theoretical rationalization", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, no. 8, 1 January 2011 (2011-01-01), pages 2702, XP055698741, ISSN: 1477-0520, DOI: 10.1039/c0ob00783h
JANIKOWSKA KAROLINA, PAWELSKA NATALIA, MAKOWIEC SŁAWOMIR: "One-Step Synthesis of β-Lactams with Retro-Amide Side Chain", SYNTHESIS, vol. 2011, no. 1, 1 January 2011 (2011-01-01), STUTTGART, DE. , pages 69 - 72, XP055931850, ISSN: 0039-7881, DOI: 10.1055/s-0030-1258966
LIU JING, TU JIANZHUO, YANG ZHANHUI, PAK CHOL-UNG, XU JIAXI: "Improved Buchner reaction selectivity in the copper-catalyzed reactions of ethyl 3-arylmethylamino-2-diazo-3-oxopropanoates", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, vol. 73, no. 31, 1 August 2017 (2017-08-01), AMSTERDAM, NL , pages 4616 - 4626, XP055931856, ISSN: 0040-4020, DOI: 10.1016/j.tet.2017.06.029
DATABASE REGISTRY 28 November 2013 (2013-11-28), ANONYMOUS : "3-Azetidinecarboxylic acid, 1-methyl-2-oxo-4-phenyl- (CA INDEX NAME)", XP055931865, retrieved from STN Database accession no. 1482712-15-1
SYNOFZIK JUDITH, DAR’IN DMITRY, NOVIKOV MIKHAIL S., KANTIN GRIGORY, BAKULINA OLGA, KRASAVIN MIKHAIL: "α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 84, no. 18, 20 September 2019 (2019-09-20), pages 12101 - 12110, XP055931860, ISSN: 0022-3263, DOI: 10.1021/acs.joc.9b02030
ZAKASZEWSKA ANNA, NAJDA-MOCARSKA EWELINA, MAKOWIEC SŁAWOMIR: "Preparation of bicyclic b-lactam and bicyclic 1,3-oxazinone scaffolds using combined cycloaddition and metathesis processes", SYNTHETIC COMMUNICATIONS, vol. 48, no. 14, 18 July 2018 (2018-07-18), US , pages 1793 - 1804, XP055931833, ISSN: 0039-7911, DOI: 10.1080/00397911.2018.1465980
ZAKASZEWSKA ANNA, NAJDA-MOCARSKA EWELINA, MAKOWIEC SŁAWOMIR: "A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties", NEW JOURNAL OF CHEMISTRY, vol. 41, no. 6, 15 February 2017 (2017-02-15), GB , pages 2479 - 2489, XP055931844, ISSN: 1144-0546, DOI: 10.1039/C7NJ00445A
ALCAIDE BENITO, ALMENDROS PEDRO, ARAGONCILLO CRISTINA, CALLEJO RICARDO, RUIZ M. PILAR: "Organocatalyzed Three-Component Ugi and Passerini Reactions of 4-Oxoazetidine-2-carbaldehydes and Azetidine-2,3-diones. Application to the Synthesis of γ-Lactams and γ-Lactones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 20, 18 October 2013 (2013-10-18), pages 10154 - 10165, XP055931847, ISSN: 0022-3263, DOI: 10.1021/jo4015358
HENGZHEN QI, XINYAO LI, JIAXI XU: "Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: experimental investigation and theoretical rationalization", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 9, no. 8, 1 January 2011 (2011-01-01), pages 2702, XP055698741, ISSN: 1477-0520, DOI: 10.1039/c0ob00783h
JANIKOWSKA KAROLINA, PAWELSKA NATALIA, MAKOWIEC SŁAWOMIR: "One-Step Synthesis of β-Lactams with Retro-Amide Side Chain", SYNTHESIS, vol. 2011, no. 1, 1 January 2011 (2011-01-01), STUTTGART, DE. , pages 69 - 72, XP055931850, ISSN: 0039-7881, DOI: 10.1055/s-0030-1258966
LIU JING, TU JIANZHUO, YANG ZHANHUI, PAK CHOL-UNG, XU JIAXI: "Improved Buchner reaction selectivity in the copper-catalyzed reactions of ethyl 3-arylmethylamino-2-diazo-3-oxopropanoates", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, vol. 73, no. 31, 1 August 2017 (2017-08-01), AMSTERDAM, NL , pages 4616 - 4626, XP055931856, ISSN: 0040-4020, DOI: 10.1016/j.tet.2017.06.029
DATABASE REGISTRY 28 November 2013 (2013-11-28), ANONYMOUS : "3-Azetidinecarboxylic acid, 1-methyl-2-oxo-4-phenyl- (CA INDEX NAME)", XP055931865, retrieved from STN Database accession no. 1482712-15-1
SYNOFZIK JUDITH, DAR’IN DMITRY, NOVIKOV MIKHAIL S., KANTIN GRIGORY, BAKULINA OLGA, KRASAVIN MIKHAIL: "α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 84, no. 18, 20 September 2019 (2019-09-20), pages 12101 - 12110, XP055931860, ISSN: 0022-3263, DOI: 10.1021/acs.joc.9b02030
Attorney, Agent or Firm:
WATANABE Kazuhira (JP)
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