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WO2004087694A1 - Composes de benzoxazine a substitution d'heterocycle presentant une bioactivite - Google Patents

Composes de benzoxazine a substitution d'heterocycle presentant une bioactivite Download PDF

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Publication number
WO2004087694A1
WO2004087694A1 PCT/CN2003/000501 CN0300501W WO2004087694A1 WO 2004087694 A1 WO2004087694 A1 WO 2004087694A1 CN 0300501 W CN0300501 W CN 0300501W WO 2004087694 A1 WO2004087694 A1 WO 2004087694A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted benzoxazine
het
compounds
ch2c
benzoxazine ring
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.)
Ceased
Application number
PCT/CN2003/000501
Other languages
English (en)
Chinese (zh)
Inventor
Zhongke Hou
Yeguo Ren
Mingzhi Huang
Manxiang Lei
Xiaoming Ou
Kaibao Zang
Xiaoguang Wang
Aiping Liu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hunan Research Institute of Chemical Industry
Original Assignee
Hunan Research Institute of Chemical Industry
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hunan Research Institute of Chemical Industry filed Critical Hunan Research Institute of Chemical Industry
Priority to AU2003304029A priority Critical patent/AU2003304029A1/en
Publication of WO2004087694A1 publication Critical patent/WO2004087694A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the invention relates to a biologically active heterocyclic substituted benzoxazine ring compound and a preparation method thereof. Background technique
  • the object of the present invention is to provide a biologically active heterocyclic substituted benzoxazine ring compound represented by the general formula (I) and a preparation method thereof.
  • the general formula (I) of the present invention is as follows: t
  • X is F, CI, CH 3 , CF 3 , CN;
  • R 2 is H, CH 3 , Ph
  • R is F, CI, Br, CH 3 , N0 2 ;
  • n represents the number of substituents, optionally 0, 1, 2, 3, 4;
  • R 1 is only CH 2 C ⁇ CI.
  • Compound (C) is reacted by adding an acid-binding agent and a halide in an appropriate solvent to obtain the target compound of general formula (I).
  • the better solvent is DMF
  • the better acid-binding agent is NaH
  • Compound (E) is added to a suitable solvent containing reduced iron powder, heated to 30 ° C to 120 ° C, and stirred for 1 hour to 12 hours to obtain (F).
  • the heterocyclic substituted benzoxazine ring compounds of the general formula (I) of the present invention have very good biological activity, and the herbicidal activity of some compounds is better than the current one.
  • the conventional herbicide used when applied at a low dose of 18.75ga.i / ha, has a 90% control effect on most broad-leaved weeds and is safer for crops such as stalks, corn, rice, and soybeans. detailed description
  • Example 1 Preparation of the 120th compound N- (7-fluoro-3-oxo 4-propynyl-1,4-benzoxazinone-6-yl) phthalimide (NO .120).
  • reaction formula is:
  • Dicotyledon choose Chenopodium album, Ramie (Abutilon theophrast) i, concave head wide
  • the growth inhibition rate (%) 100 (control plant height-treated plant height) I control plant height.
  • the herbicidal activity is graded: A-level growth inhibition rate> 90%; B-level growth inhibition rate 75 90%; C-level growth inhibition rate 50 ⁇ 75%; D-level growth inhibition rate is less than 50%.
  • Some compounds of the present invention such as compounds N0.69, 120, 137, and 626, were used to treat stem and leaves of potted test plants after buds at an application rate of 18.75ga.i / ha.
  • Compound NO. 120 is safe for sorghum at a dose of 37.5ga.i / ha; it is safe for rice, corn, and soybeans at a lower dose of 18.75ga.i / ha. But it is not safe for rapeseed and wheat.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Secondary Cells (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés de benzoxazine à substitution d'hétérocycle représentés par la formule (I), et un procédé de préparation de ceux-ci. Dans la formule, Het est représenté par (II) ou (III) ; Y représente O, S ; w égale 0, 1 ; X représente F, Cl, CH3, CF3, CN ; R2 représente H, CH3, Ph ; R représente F, Cl, Br, CH3, NO2 ; m représente le nombre de substituants et est choisi parmi 0, 1, 2, 3, 4 ; lorsque Het est représenté par (II), R1 représente CH3, CHF2, CH2CH3, CH2CN, CH2CH2CH3, CH2CH2=CH2, CH2C CH, CH2C C-Br, CH2C C-Cl, CH2C C-I, CH2OCH2CH3 ; lorsque Het est représenté par (III), R1 représente uniquement CH2C C-I. Les composés de l'invention possèdent une excellente activité herbicide lorsqu'ils sont appliqués à faible dose, p. ex. 18,75 ga.i/ha, une partie des composés présente une efficacité ≥ 90 % contre la plupart des mauvaises herbes à feuilles larges et sont sans danger pour des cultures telles que le sorgho, le maïs, le riz, le soja, etc.
PCT/CN2003/000501 2003-03-31 2003-06-27 Composes de benzoxazine a substitution d'heterocycle presentant une bioactivite Ceased WO2004087694A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003304029A AU2003304029A1 (en) 2003-03-31 2003-06-27 A heterocycle-substituted benzoxazine compounds having bioactivity

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN03118226.7 2003-03-31
CNB031182267A CN1194975C (zh) 2003-03-31 2003-03-31 一种具有生物活性的杂环取代苯并噁嗪环类化合物

Publications (1)

Publication Number Publication Date
WO2004087694A1 true WO2004087694A1 (fr) 2004-10-14

Family

ID=27797197

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2003/000501 Ceased WO2004087694A1 (fr) 2003-03-31 2003-06-27 Composes de benzoxazine a substitution d'heterocycle presentant une bioactivite

Country Status (3)

Country Link
CN (1) CN1194975C (fr)
AU (1) AU2003304029A1 (fr)
WO (1) WO2004087694A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
CN102920709A (zh) * 2012-11-15 2013-02-13 山东大学齐鲁医院 2,3-二氢-3-羟甲基-6-甲基-[1,4]-苯并噁嗪在制备抗乳腺癌药物中的应用
WO2014122674A1 (fr) * 2013-02-08 2014-08-14 Rallis India Limited Procédé de préparation de dérivés de tétrahydrophtalimide
US9101634B2 (en) 2010-05-20 2015-08-11 Shandong University Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells
US10285923B2 (en) 2011-12-20 2019-05-14 Johnson & Johnson Consumer Inc. Cationic polyglyceryl compositions and compounds
WO2019101513A1 (fr) 2017-11-23 2019-05-31 Basf Se Pyridyléthers en tant qu'herbicides

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100387582C (zh) * 2005-06-21 2008-05-14 湖南化工研究院 具有除草活性的n-羧酸衍生物取代的苯并噁嗪类化合物
EP2443102B1 (fr) * 2009-06-19 2013-04-17 Basf Se Benzoxazinones herbicides
EP2794599A1 (fr) * 2011-12-23 2014-10-29 Basf Se Procédé de fabrication de triazinone-benzoxazinones
JP6156074B2 (ja) * 2013-11-08 2017-07-05 住友化学株式会社 スクシンイミド化合物及びその用途
JP7295088B2 (ja) * 2017-07-24 2023-06-20 レダッグ クロップ プロテクション リミテッド 除草剤として有用なベンゾオキサジノン誘導体

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640707A (en) * 1984-07-23 1987-02-03 Sumitomo Chemical Company, Ltd. Tetrahydrophthalimides and their herbicidal use
US4975114A (en) * 1988-10-04 1990-12-04 Sumitomo Chemical Company, Limited Herbicidal composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640707A (en) * 1984-07-23 1987-02-03 Sumitomo Chemical Company, Ltd. Tetrahydrophthalimides and their herbicidal use
US4975114A (en) * 1988-10-04 1990-12-04 Sumitomo Chemical Company, Limited Herbicidal composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9101634B2 (en) 2010-05-20 2015-08-11 Shandong University Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
US10285923B2 (en) 2011-12-20 2019-05-14 Johnson & Johnson Consumer Inc. Cationic polyglyceryl compositions and compounds
CN102920709A (zh) * 2012-11-15 2013-02-13 山东大学齐鲁医院 2,3-二氢-3-羟甲基-6-甲基-[1,4]-苯并噁嗪在制备抗乳腺癌药物中的应用
WO2014122674A1 (fr) * 2013-02-08 2014-08-14 Rallis India Limited Procédé de préparation de dérivés de tétrahydrophtalimide
WO2019101513A1 (fr) 2017-11-23 2019-05-31 Basf Se Pyridyléthers en tant qu'herbicides

Also Published As

Publication number Publication date
CN1442416A (zh) 2003-09-17
AU2003304029A1 (en) 2004-10-25
CN1194975C (zh) 2005-03-30

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