Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 70, Issue 29, Pages 8986-8993Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.2c02954
Keywords
QSAR; docking; herbicides; HPPD enzyme; aryloxyacetic acids
Funding
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) [001]
- Conselho Nacional de Desenvolvimento Cientifico e Tecnolgico (CNPq) [306830/2021-3]
- Fundacao de Amparo a Pesquisado Estadode Minas Gerais (FAPEMIG)
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Aryloxyacetic acid derivatives showed promising herbicidal performance through inhibition of HPPD enzyme. By using QSAR and docking strategies, new analogues were proposed to improve herbicidal properties and minimize ecological issues.
A series of aryloxyacetic acid derivatives have demonstrated promising herbicidal performance by inhibition of the hydroxyphenylpyruvate deoxygenase (HPPD) enzyme. We hereby applied quantitative structure-activity relationship (QSAR) and docking strategies to model and chemically understand the bioactivities of these compounds and subsequently propose unprecedented analogues aiming at improving the herbicidal and environmental properties. Bulky halogens at the 2-, 3-, 4-, and 6-positions of an aromatic ring, CF3 in 4-position, and the 2-NO2 group in a phenyl ring appear to favor the HPPD inhibition. At the same time, Me and OMe substituents contribute to decreasing the pKi values. Accordingly, a few compounds were proposed and the candidate with 2,4,6-triBr substituents demonstrated an estimated pKi similar to those of the best library compounds. This finding was corroborated by the docking scores of the ligand-enzyme interactions. In addition, the high calculated lipophilicity of some proposed agrochemicals suggests that they should have low soil mobility and, therefore, are not prone to easily leach out and reach groundwater, despite causing other ecological issues.
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