Novel HPPD inhibitors: triketone 2H-benzo[b][1,4]oxazin-3(4H)-one analogs

被引:26
|
作者
Li, Hua-Bin [1 ,2 ]
Li, Lei [1 ]
Li, Jun-Xian [1 ]
Han, Ting-Feng [1 ]
He, Jing-Li [1 ]
Zhu, You-Quan [1 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin, Peoples R China
[2] Nankai Univ, Coll Chem, Natl Pesticide Engn Res Ctr Tianjin, Tianjin, Peoples R China
基金
中国国家自然科学基金;
关键词
HPPD; herbicidal activity; benzoxazinone; synthesis; triketone; 4-HYDROXYPHENYLPYRUVATE DIOXYGENASE; HERBICIDAL ACTIVITY;
D O I
10.1002/ps.4739
中图分类号
S3 [农学(农艺学)];
学科分类号
0901 ;
摘要
BACKGROUND: Herbicides that inhibit 4-hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) are very important for grass weed control. In order to discover novel HPPD herbicides, a series of triketone 2H-benzo[b] oxazin-3(4H)-one analogs was designed and synthesized. RESULTS: In comparison with the commercial triketone HPPD herbicide mesotrione (IC50 = 0.252 M), some of these new triketone analogs displayed excellent HPPD inhibitory potency in vitro, for example B39 (IC50 = 0.172 M) and B41 (IC50 = 0.156 M). In addition, some of these compounds exhibited pre- and post-emergence herbicidal activity similar to mesotrione when applied at 375 g/ha. CONCLUSION: Many of the title compounds described in this paper could be important lead structures for the further development of novel HPPD herbicides. (C) 2017 Society of Chemical Industry
引用
收藏
页码:579 / 589
页数:11
相关论文
共 50 条
  • [41] SYNTHESIS AND STUDY OF 1,2-BIS(8-ALLYL-2H-BENZO[E][1,3]OXAZIN-3(4H)YL)ETHANE AND ITS STRUCTURING PRODUCTS
    Mehdiyeva, Gunay M.
    Bayramov, Musa R.
    PROCESSES OF PETROCHEMISTRY AND OIL REFINING, 2024, 25 (01): : 141 - 152
  • [42] 'Vanilla Oceanics': Synthesis and Olfactory Properties of (1′E)-7-(Prop-1′-enyl)-2H-benzo[b][1,4]dioxepin-3(4H)-ones and Homologues
    Kraft, Philip
    Popaj, Kasim
    Mueller, Peter
    Schaer, Michael
    SYNTHESIS-STUTTGART, 2010, (17): : 3029 - 3036
  • [43] PREPARATION OF 2H-PYRIDO[3,2-B]-1,4-OXAZIN-3(4H)-ONES AND OF CORRESPONDING DIHYDROPYRIDOOXAZINES
    CLAUSONKAAS, N
    HEIDE, H
    OLSEN, G
    ACTA CHEMICA SCANDINAVICA, 1969, 23 (07): : 2322 - +
  • [44] Synthesis, structure, and stereochemical non-rigidity of bis[(2,2-dimethyl-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)methyl] dichlorosilane and -germane
    Negrebetsky V.V.
    Kramarova E.P.
    Arkhipov D.E.
    Korlyukov A.A.
    Shipov A.G.
    Baukov Y.I.
    Russian Chemical Bulletin, 2015, 64 (8) : 1808 - 1813
  • [45] Synthesis, structure, and stereochemical non-rigidity of bis[(2,2-dimethyl-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)methyl]dichlorosilane and -germane
    Negrebetsky, Vad. V.
    Kramarova, E. P.
    Arkhipov, D. E.
    Korlyukov, A. A.
    Shipov, A. G.
    Baukov, Yu. I.
    RUSSIAN CHEMICAL BULLETIN, 2015, 64 (08) : 1808 - 1813
  • [46] Potentiometric and Theoretical Studies of (2Z, 3Z)-2H-benzo[b][1,4]thiazine-2,3(4H)-dionedioxime with Some Divalent Transition Metal Ions
    Faisal N. Al-Obaidi
    Hasan Atabey
    Mustafa Macit
    Hayati Sari
    Journal of Solution Chemistry, 2014, 43 : 989 - 999
  • [47] Potentiometric and Theoretical Studies of (2Z, 3Z)-2H-benzo[b][1,4]thiazine-2,3(4H)-dionedioxime with Some Divalent Transition Metal Ions
    Al-Obaidi, Faisal N.
    Atabey, Hasan
    Macit, Mustafa
    Sari, Hayati
    JOURNAL OF SOLUTION CHEMISTRY, 2014, 43 (05) : 989 - 999
  • [48] Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones
    Cho, SD
    Song, SY
    Park, YD
    Kim, JJ
    Joo, WH
    Shiro, M
    Falck, JR
    Shin, DS
    Yoon, YJ
    TETRAHEDRON LETTERS, 2003, 44 (50) : 8995 - 8998
  • [49] Microwave Synthesis of Chiral N-Benzyl-2-methyl-2H-benzo[b][1,4]oxazin/thiazin-3(4H)-ones via Smiles Rearrangement and their Biological Evaluation
    Meng, Li-juan
    Zuo, Hua
    Vijaykumar, B. V. D.
    Dupati, Gautam
    Choi, Kyung-Min
    Jang, Kiwan
    Yoon, Yong-Jin
    Shin, Dong-Soo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (02): : 585 - 589
  • [50] REARRANGEMENT OF 4-ACETOXY-2H-1,4-BENZOXAZIN-3(4H)-ONE
    HASHIMOTO, Y
    ISHIZAKI, T
    SHUDO, K
    OKAMOTO, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1983, 31 (11) : 3891 - 3896