Design, Synthesis, Mode of Action and Herbicidal Evaluation of Quinazolin-4(3<i>H</i>)-one Derivatives Based on Aryloxyphenoxypropionate Motif
2022
Chaochao Wang | Ke Chen | Na Li | Shuyue Fu | Pan Li | Lusha Ji | Guoyun Liu | Xuekun Wang | Kang Lei
To discover new acetyl-CoA carboxylase (ACCase) inhibiting-based herbicides, twenty-nine novel quinazolin-4(3<i>H</i>)-one derivatives were designed and synthesized based on the aryloxyphenoxypropionate motif. The bioassay results showed that most of the target compounds showed better pre-emergent herbicidal activity against monocotyledonous weeds in a greenhouse. Especially, when applied at 375 g ha<sup>−1</sup> under pre-emergence conditions, compound <b>QPP-7</b> displayed excellent herbicidal activity against monocotyledonous weeds (i.e., <i>E. crusgalli</i>, <i>D. sanguinalis, P. alopecuroides</i>, <i>S. viridis</i>, <i>E. indica</i>, <i>A. fatua</i>, <i>E. dahuricu</i>, <i>S. alterniflora</i>) with inhibition rate >90%, and displayed excellent crop safety to <i>O. sativa</i>, <i>T. aestivum</i>, <i>G. spp</i>, and <i>A. hypogaea.</i> The study of structure-activity relationship (SAR) revealed that the herbicidal activity of target compounds is strongly influenced by the spatial position of R group and the bulk of R<sub>1</sub> group on quinazolin-4(3<i>H</i>)-one, and the (R = 6-F, R<sub>1</sub> = Me) pattern is confirmed as the optimal orientation. Furthermore, the molecular docking study and the good inhibitory activity of <b>QPP-7</b> against <i>E. crusgalli</i> ACCase enzyme (IC<sub>50</sub> = 54.65 nM) indicated that it may be a ACCase inhibitor. Taken together, the present work demonstrated that compound <b>QPP-7</b> could serve as a potential lead structure for further developing novel ACCase inhibiting-based herbicide.
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