Synthesis and Herbicidal Activity of Pyrido[2,3-d]pyrimidine-2,4-dione-Benzoxazinone Hybrids as Protoporphyrinogen Oxidase Inhibitors

被引:53
|
作者
Wang, Da-Wei [1 ,2 ]
Li, Qian [1 ,2 ]
Wen, Kai [1 ,2 ]
Ismail, Ismail [1 ,2 ]
Liu, Dan-Dan [1 ,2 ]
Niu, Cong-Wei [1 ,2 ]
Wen, Xin [1 ,2 ]
Yang, Guang-Fu [3 ]
Xi, Zhen [1 ,2 ]
机构
[1] Nankai Univ, State Key Lab Elementoorgan Chem, Coll Chem, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
[2] Nankai Univ, Dept Chem Biol, Coll Chem, Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300071, Peoples R China
[3] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
pyrido[2,3-d]pyrimidine-2,4-dione; benzoxazinone; protoporphyrinogen oxidase; herbicide; structure-activity relationship; 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE INHIBITORS; STRUCTURAL INSIGHT; BACILLUS-SUBTILIS; QUINAZOLINE-2,4-DIONES; IDENTIFICATION; FLUMIOXAZIN; DERIVATIVES; MECHANISM; MUTATION; DESIGN;
D O I
10.1021/acs.jafc.7b01990
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
To search for new protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors with improved bioactivity, a series of novel pyrido[2,3-d]pyrimidine-2,4-dione benzoxazinone hybrids, 9-13, were designed and synthesized. Several compounds with improved tobacco PPO (mtPPO)-inhibiting and promising herbicidal activities were found. Among them, the most potent compound, 3-(7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-benzo[b][1,4] oxazin-6-yl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione, 11q, with a K-i value of 0.0074 mu M, showed six times more activity than flumioxazin (K-i = 0.046 mu M) against mtPPO. Compound 11q displayed a strong and broad spectrum of weed control at 37.5-150 g of active ingredient (ai)/ha by both post- and pre-emergence application, which was comparable to that of flumioxazin. 11q was safe to maize, soybean, peanut, and cotton at 150 g ai/ha, and selective to rice and wheat at 75 g ai/ha by pre-emergence application, indicating potential applicability in these fields.
引用
收藏
页码:5278 / 5286
页数:9
相关论文
共 50 条
  • [1] SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDINE-2,4-DIONES
    WAWZONEK, S
    JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19): : 3149 - 3151
  • [2] REGIOSELECTIVE SYNTHESIS OF PYRROLO[2,3-D]-PYRIMIDINE-2,4-DIONES AND "PYRIDO[2,3-D]-PYRIMIDINE-2,4-DIONES
    TAMURA, Y
    SAKAGUCHI, T
    KAWASAKI, T
    KITA, Y
    HETEROCYCLES, 1975, 3 (02) : 183 - 186
  • [3] Synthesis and biological evaluation of pyrido[2,3-d]pyrimidine-2,4-dione derivatives as eEF-2K inhibitors
    Edupuganti, Ramakrishna
    Wang, Qiantao
    Tavares, Clint D. J.
    Chitjian, Catrina A.
    Bachman, James L.
    Ren, Pengyu
    Anslyn, Eric V.
    Dalby, Kevin N.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (17) : 4910 - 4916
  • [4] Syntheses and evaluation of pyrido[2,3-d]pyrimidine-2,4-diones as PDE 4 inhibitors
    Nam, G
    Yoon, CM
    Kim, E
    Rhee, CK
    Kim, JH
    Shin, JH
    Kim, SH
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (05) : 611 - 614
  • [5] SYNTHESIS OF BENZOFURO[2,3-D]PYRIMIDINE-2,4-DIONES
    STADLBAUER, W
    MONATSHEFTE FUR CHEMIE, 1989, 120 (01): : 77 - 80
  • [6] Discovery of pyrano[2,3-d]pyrimidine-2,4-dione derivatives as novel PARP-1 inhibitors: design, synthesis and antitumor activity
    Abd El-sattar, Nour E. A.
    Badawy, Eman H. K.
    Elrazaz, Eman Z.
    Ismail, Nasser S. M.
    RSC ADVANCES, 2021, 11 (08) : 4454 - 4464
  • [7] The discovery and optimisation of pyrido[2,3-d]pyrimidine-2,4-diamines as potent and selective inhibitors of mTOR kinase
    Malagu, Karine
    Duggan, Heather
    Menear, Keith
    Hummersone, Marc
    Gomez, Sylvie
    Bailey, Christine
    Edwards, Peter
    Drzewiecki, Jan
    Leroux, Frederic
    Quesada, Mar Jimenez
    Hermann, Gesine
    Maine, Stephanie
    Molyneaux, Carrie-Anne
    Le Gall, Armelle
    Pullen, James
    Hickson, Ian
    Smith, Lisa
    Maguire, Sharon
    Martin, Niall
    Smith, Graeme
    Pass, Martin
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (20) : 5950 - 5953
  • [8] Synthesis of Pyrano[2,3-d]pyrimidine-2,4-diones and Pyridino[2,3-d]pyrimidine-2,4,6,8-tetraones: Evaluation Antitumor Activity
    Haggam, Reda A.
    Assy, Mohamed G.
    Mohamed, Enaiat K.
    Mohamed, Abdussattar S.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (02) : 842 - 850
  • [9] SYNTHESIS OF SUBSTITUTED "PYRROLO[2,3-D]PYRIMIDINE-2,4-DIONES
    ETSON, SR
    MATTSON, RJ
    SOWELL, JW
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (05) : 929 - 933
  • [10] Synthesis, Herbicidal Activity, and QSAR of Novel N-Benzothiazolyl-pyrimidine-2,4-diones as Protoporphyrinogen Oxidase Inhibitors
    Zuo, Yang
    Wu, Qiongyou
    Su, Sun-wen
    Niu, Cong-wei
    Xi, Zhen
    Yang, Guang-Fu
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2016, 64 (03) : 552 - 562