Improving the Activity of Aminophenoxazinones: Synthesis, CPC Purification, and Phytotoxicity Potential
Cristina Díaz-Franco, Carlos Rial, Stefan Schwaiger, Rosa M. Varela, Francisco A. Macías, José M. G. Molinillo
TL;DR
This paper describes the synthesis and purification of aminophenoxazinone derivatives that show strong phytotoxic effects, making them promising candidates for sustainable herbicides.
Contribution
A novel purification method and structure-activity relationship analysis led to the discovery of a highly potent agrochemical lead.
Findings
Compound 11 caused 89% root inhibition in Portulaca oleracea at 1000 μM.
Compound 10 exhibited an IC50 of 4.5 μM against P. oleracea roots, much lower than natural APO.
Centrifugal partition chromatography successfully purified APO derivatives with strong compound-solid phase interactions.
Abstract
Aminophenoxazinones (APOs) are potent phytotoxic metabolites and histone deacetylase inhibitors, offering a low-resistance bioherbicide profile. This research synthesized a library of APO derivatives with targeted modifications to optimize physicochemical properties and biological activity using oxidative cyclocondensation. Purification challenges from strong compound-solid phase interactions were overcome by using centrifugal partition chromatography (CPC). Phytotoxicity was screened against Lolium rigidum, Portulaca oleracea, and Plantago lanceolata. While germination remained largely unaffected, compounds 10 and 11 caused significant root inhibition (77% and 89%, respectively for P. oleracea) at 1000 μM. Specifically, 11 reached inhibition levels comparable to the positive control, pendimethalin (86% for P. oleracea). Following a detailed structure–activity relationship analysis, 10…
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Taxonomy
TopicsAllelopathy and phytotoxic interactions · Synthesis of Organic Compounds · Phenothiazines and Benzothiazines Synthesis and Activities