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Design, Synthesis, and Herbicidal Activity Evaluation of Novel Aryl-Naphthyl Methanone Derivatives

Overview
Journal Front Chem
Specialty Chemistry
Date 2019 Feb 7
PMID 30723715
Citations 8
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Abstract

4-Hydroxyphenylpyruvate dioxygenase (HPPD) is one of the most vital targets for herbicides discovery. In search for HPPD inhibitors with novel scaffolds, a series of aryl-naphthyl methanone derivatives have been designed and synthesized through alkylation and Friedel-Crafts acylation reactions. The bioassay indicated some of these compounds displayed preferable herbicidal activity at the rate of 0.75 mmol/m by post-emergence application, in which compound displayed the best herbicidal activity. The molecular docking showed that compound could bind well to the active site of the HPPD. This study shows that aryl-naphthyl methanone derivatives could be a potential lead structure for further development of novel herbicides.

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References
1.
Pauly J, Spiteller D, Linz J, Jacobs J, Allen C, Nett M . Ralfuranone thioether production by the plant pathogen Ralstonia solanacearum. Chembiochem. 2013; 14(16):2169-78. DOI: 10.1002/cbic.201300364. View

2.
Santucci A, Bernardini G, Braconi D, Petricci E, Manetti F . 4-Hydroxyphenylpyruvate Dioxygenase and Its Inhibition in Plants and Animals: Small Molecules as Herbicides and Agents for the Treatment of Human Inherited Diseases. J Med Chem. 2017; 60(10):4101-4125. DOI: 10.1021/acs.jmedchem.6b01395. View

3.
Kubo T, Ohno M, Nagasawa S, Kose T, Kawata K . Behavior of herbicide pyrazolynate and its hydrolysate in paddy fields after application. Bull Environ Contam Toxicol. 2012; 89(5):985-9. DOI: 10.1007/s00128-012-0793-6. View

4.
Ahrens H, Lange G, Muller T, Rosinger C, Willms L, van Almsick A . 4-Hydroxyphenylpyruvate dioxygenase inhibitors in combination with safeners: solutions for modern and sustainable agriculture. Angew Chem Int Ed Engl. 2013; 52(36):9388-98. DOI: 10.1002/anie.201302365. View

5.
Ndikuryayo F, Moosavi B, Yang W, Yang G . 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors: From Chemical Biology to Agrochemicals. J Agric Food Chem. 2017; 65(39):8523-8537. DOI: 10.1021/acs.jafc.7b03851. View