Facile synthesis and herbicidal evaluation of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with 2-phenoxymethyl substituents

Molecules

Volumn 17, Issue 3, 2012, Pages 3181-3201

  Aibibuli, Zumuretiguli ^a   Wang, Yufeng ^a   Tu, Haiyang ^a   Huang, Xiaoting ^a   Zhang, Aidong ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

3H quinazolin 4 ones; 4H 3,1 benzoxazin 4 ones; Active substructure combination; Auxinic receptor TIR1; Herbicidal activity

Indexed keywords

BENZOXAZINE DERIVATIVE; DIPHENYL ETHER DERIVATIVE; HERBICIDE; QUINAZOLINONE DERIVATIVE; VEGETABLE PROTEIN;

ARTICLE; BINDING SITE; BRASSICA RAPA; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECT; ECHINOCHLOA; GROWTH, DEVELOPMENT AND AGING; IC 50; PLANT ROOT; PLANT STEM; PROTEIN BINDING; SYNTHESIS;

BENZOXAZINES; BINDING SITES; BRASSICA RAPA; CHEMISTRY TECHNIQUES, SYNTHETIC; COMPUTER SIMULATION; ECHINOCHLOA; HERBICIDES; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; PHENYL ETHERS; PLANT PROTEINS; PLANT ROOTS; PLANT STEMS; PROTEIN BINDING; QUINAZOLINONES;

EID: 84858984915     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17033181     Document Type: Article

References (20)

1. Gierl, A.; Frey M. Evolution of benzoxazinone biosynthesis and indole production in maize. Planta 2001, 213, 493-498. (Pubitemid 32792465)
2. Macias, F. A.; Siqueira, J. M. D.; Chinchilla, N.; Marin, D.; Varela, R. M.; Molinillo, J. M. G. New herbicide models from benzoxazinones: Aromatic ring functionalization effects. J. Agric. Food Chem. 2006, 54, 9843-9851. (Pubitemid 46158979)
3. Huang, M.; Luo, F.; Mo, H.; Ren, Y.; Wang, X.; Ou, X.; Lei, M.; Liu, A.; Huang, L.; Xu, M. Synthesis and herbicidal activity of isoindoline-1, 3-dione substituted benzoxazinone derivatives containing a carboxylic ester group. J. Agric. Food Chem. 2009, 57, 9585-9592.
4. Hsieh, P.-W.; Hwang, T.-L.; Wu, C.-C.; Chang, F.-R.; Wang, T.-W.; Wu, Y.-C. The evaluation of 2, 8-disubstituted benzoxazinone derivatives as anti-inflammatory and anti-platelet aggregation agents. Bioorg. Med. Chem. Lett. 2005, 15, 2786-2789. (Pubitemid 40732220)
5. Hsieh, P.-W.; Yu, H.-P.; Chang, Y.-J.; Hwang, T.-L. Synthesis and evaluation of benzoxazinone derivatives on activity of human neutrophil elastase and on hemorrhagic shock-induced lung injury in rats. Eur. J. Med. Chem. 2010, 45, 3111-3115.
6. Anderson, R.; Breazeale, S.; Elich, T.; Lee, S.-F. Modulators of acetyl-coenzyme a carboxylase and methods of use thereof. U. S. Patent US20100009982A1, 14 Janurary 2010.
7. Stephen, M. G.; Chen, Y.-C. S.; Fabbri, B. J.; Yalamanchili, G.; Hamper, B. C.; Walker, D. M.; Brookfield, F. A.; Boyd, E. A.; Ashton, M. R.; Yarnold, C. J.; CaJacob, C. A. The carboxy terminal processing protease of D1 protein Herbicidal activity of novel inhibitors of the recombinant and native spinach enzymes. Pestic. Biochem. Physiol. 2007, 88, 1-13. (Pubitemid 46341396)
8. Lisurek, M.; Rupp, B.; Wichard, J.; Neuenschwander, M.; von Kries, J. P.; Frank, R.; Rademann, J.; Kühne, R. Design of chemical libraries with potentially bioactive molecules applying a maximum common substructure concept. Mol. Divers. 2010, 14, 401-408.
9. The World of Herbicides According to HRAC classification on mode of action 2010, a free poster designed and produced by Syngenta. Available online: http://www.hracglobal.com (accessed on 28 February 2012).
10. Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. Design and synthesis of 4H-3, 1-benzoxazin-4-ones as potent alternate substrate inhibitors of human leukocyte elastase. J. Med. Chem. 1990, 33, 464-479. (Pubitemid 20047560)
11. Shariat, M.; Abdollah, S. Synthesis of benzoxazinone derivatives: A new route to 2-(N-phthaloylmethyl)-4H-3, 1-benzoxazin-4-ones. Molecules 2004, 9, 705-712. (Pubitemid 39375350)
12. Shishoo, C. J.; Shirsath, V. S.; Rathod, I. S.; Yande, V. D. Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4 (3H)-ones. Eur. J. Med. Chem. 2000, 35, 351-358. (Pubitemid 30187067)
13. Zhu, Y. Q.; Wu, C.; Li, H. B.; Zou, X. M. Design, synthesis and quantitative structure-activity relationship study of herbicidal analogues of pyrazolo[5, 1-d][1, 2, 3, 5]tetrazin-4 (3H)-ones. J. Agric. Food Chem. 2007, 55, 1364-1369.
14. Dharmasiri, N.; Dharmasiri, S.; Estelle, M. The F-box protein TIR1 is an auxin receptor. Nature 2005, 435, 441-445. (Pubitemid 40734235)
15. Trott, O.; Olson, A. J. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading. J. Comput. Chem. 2010, 31, 455-461.
16. Tan, X.; Calderon-Villalobos, L. I. A.; Sharon, M.; Zheng, C.; Robinson, C. V.; Estelle, M.; Zheng, N. Mechanism of auxin perception by the TIR1 ubiquitin ligase. Nature 2007, 446, 640-645. (Pubitemid 46606890)
17. Hayashi, K.-I.; Tan, X.; Zheng, N.; Hatate, T.; Kimura, Y.; Kepinski, S.; Nozaki, H. Small-molecule agonists and antagonists of F-box protein-substrate interactions in auxin perception and signaling. Proc. Natl. Acad. Sci. USA 2008, 105, 5632-5637. (Pubitemid 351753914)
18. Tarasov, A. V.; Strikanova, O. N.; Moskvichev, Y. A.; Timoshenko, G. N. Synthesis of 3-(4-Oxo-4H-3, 1-benzoxazin-2-yl)-1-benzenesulfonyl Chloride and Its Reactivity toward Amines. Russ. J. Org. Chem. 2002, 38, 87-89. (Pubitemid 37116905)
19. El-Azab, A. S.; Al-Omar, M. A.; Abdel-Aziz, A. A.-M.; Abdel-Aziz, N. I.; El-Sayed, M. A.-A.; Aleisa, A. M.; Sayed-Ahmed, M. M.; Abdel-Hamide, S. G. Design, synthesis and biological evaluation of novel quinazoline derivatives as potential antitumor agents: Molecular docking study. Eur. J. Med. Chem. 2010, 45, 4188-4198.
20. Zhu, Y. Q.; Wu, C.; Li, H. B.; Zou, X. M. Design, synthesis, and quantitative structure-activity relationship study of herbicidal analogues of pyrazolo[5, 1-d][1, 2, 3, 5] tetrazin-4 (3H)-ones. J. Agric. Food Chem. 2007, 55, 1364.