Herbicidal activity of isobenzofuranones and in silico identification of their enzyme target.
BACKGROUND
Given the weed resistance to various herbicides with different mechanisms of action, the search for new compounds that are more effective and exhibit low levels of impact to other species in nature has been imperative in the field of the agriculture. For this purpose, 16 phthalides, and furan-2(5H)-one were synthetized and evaluated for their effectiveness as herbicides in seeds of Sorghum bicolor (sorghum), Cucumis sativus (cucumber), and Allium cepa (onion). Furthermore, a preliminary in silico study was carried out to identify the enzyme target of the most active compounds.


RESULTS
In the assays with S. bicolor, the mixture rac-(3aR,4R,5S,6S,7S,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one + rac-(3aR,4R,5R,6R,7S,7aS)-5,6-dibromohexahydro-4,7-methanoisobenzofuran-1(3H)-one (15a + 15b) showed comparable inhibitory activity to (S)-metolachlor, which was used as control herbicide at concentrations ranging from 50 μm to 1000 μm. The developments of the seeds evaluated were altered by all 17 compounds, either stimulating or inhibiting. The best results were presented by compounds 15a, and 15b, either in their pure form or as a mixture.


CONCLUSION
The results presented by 15a, and 15b were superior to the activity of the commercial herbicide (S)-metolachlor in the assays with C. sativus, and A. cepa. The in silico study provides strong evidence that the most active compounds bind to strigolactones esterases D14 through the same binding site of (5R)-5-hydroxy-3-methylfuran-2(5H)-one (H3M), which is one of the strigolactones (SLs) cleavage products. © 2019 Society of Chemical Industry.
['Teixeira|Milena G|MG|', 'Alvarenga|Elson S|ES|https://orcid.org/0000-0002-7333-0006', 'Lopes|Dayane T|DT|', 'Oliveira|Denilson F|DF|']
D001572:Benzofurans D003198:Computer Simulation D018553:Cucumis sativus D006540:Herbicides D019697:Onions D012639:Seeds D045868:Sorghum
herbicide phthalides sorghum cucumber onion