Design, Synthesis, Mode of Action and Herbicidal Evaluation of Quinazolin-4(3H)-one Derivatives Based on Aryloxyphenoxypropionate Motif
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Information
2.2. Chemical Synthesis Procedures
2.2.1. General Procedure for the Synthesis of Intermediates 2a–2o and 5a–5n
2.2.2. General Procedure for the Synthesis of Intermediates 3a–3o and 6a–6n
2.2.3. General Procedure for the Synthesis of Target Compounds QPP-1 to QPP-29
2.3. X-ray Diffraction Analysis of Target Compound QPP-7
2.4. Evaluation of Herbicidal Activity
2.5. Crop Selectivity
2.6. Molecular Docking Study
2.7. ACCase Extraction and Inhibition Activity Assay
3. Results and Discussion
3.1. Synthetic Chemistry
3.2. In Vitro Herbicidal Activity of Target Compounds QPP-1 to QPP-15
3.3. Herbicidal Activity of Target Compounds QPP-1 to QPP-29 in Greenhouse Tests and SAR Study
3.4. Herbicidal Spectrum and Crop Safety of Compound QPP-7
3.5. Molecular Mode of Action of the Target Compound QPP-7
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Comp. | Rate (g ha−1) | B. campestris | A. retroflexus | E. crusgalli | D. sanguinalis | ||||
---|---|---|---|---|---|---|---|---|---|
Pre | Post | Pre | Post | Pre | Post | Pre | Post | ||
QPP-3 | 750 | 8.3 ± 1.7 | 0 | 0 | 0 | 94.5 ± 1.3 | 24.7 ± 1.6 | 88.9 ± 0.2 | 1.9 ± 0.4 |
375 | 0 | 0 | 0 | 0 | 60.4 ± 1.4 | 5.0 ± 1.0 | 76.7 ± 1.3 | 0 | |
187.5 | 0 | 0 | 0 | 0 | 45.0 ± 2.1 | 0 | 48.9 ± 1.8 | 0 | |
QPP-7 | 750 | 7.8 ± 0.9 | 0 | 4.8 ± 0.2 | 0 | 100 | 42.1 ± 0.6 | 100 | 61.6 ± 1.9 |
375 | 0 | 0 | 0 | 0 | 96.7 ± 1.6 | 24.0 ± 0.6 | 100 | 21.3 ± 1.2 | |
187.5 | 0 | 0 | 0 | 0 | 64.8 ± 3.1 | 0 | 55.6 ± 1.4 | 0 | |
QPP-11 | 750 | 4.2 ± 0.3 | 6.6 ± 0.4 | 0 | 0 | 91.2 ± 1.5 | 15.7 ± 1.3 | 84.4 ± 0.8 | 13.2 ± 0.4 |
375 | 0 | 0 | 0 | 0 | 75.8 ± 0.4 | 10.2 ± 1.0 | 72.2 ± 1.1 | 6.6 ± 0.1 | |
187.5 | 0 | 0 | 0 | 0 | 60.4 ± 0.8 | 0 | 53.3 ± 2.0 | 0 | |
QZ | 750 | 38.6 ± 2.3 | 7.0 ± 1.1 | 31.2 ± 0.7 | 0 | 100 | 100 | 100 | 100 |
375 | 24.5 ± 1.7 | 0 | 20.6 ± 1.3 | 0 | 100 | 100 | 100 | 100 | |
187.5 | 11.1 ± 0.6 | 0 | 10.5 ± 1.7 | 0 | 97.8 ± 1.7 | 100 | 100 | 100 |
Comp. | % Injury | |||||
---|---|---|---|---|---|---|
O. sativa | Z. mays | T. aestivum | G. spp | G. max | A. hypogaea | |
QPP-7 | 0 | 55.5 ± 1.4 | 0 | 10.9 ± 1.1 | 4.5 ± 0.4 | 0 |
QZ | 98.7 ± 0.9 | 16.8 ± 1.7 | 59.3 ± 1.2 | 0 | 0 | 0 |
Comp. | Regression Equation | IC50 (nM) | 95% Confidence Interval | r |
---|---|---|---|---|
QPP-7 | y = 0.4842x + 16.9 | 54.65 | 40.26 to 82.67 | 0.9751 |
QZ | y = 0.4449x + 24.2 | 41.19 | 27.82 to 69.67 | 0.9585 |
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Wang, C.; Chen, K.; Li, N.; Fu, S.; Li, P.; Ji, L.; Liu, G.; Wang, X.; Lei, K. Design, Synthesis, Mode of Action and Herbicidal Evaluation of Quinazolin-4(3H)-one Derivatives Based on Aryloxyphenoxypropionate Motif. Agronomy 2022, 12, 1840. https://doi.org/10.3390/agronomy12081840
Wang C, Chen K, Li N, Fu S, Li P, Ji L, Liu G, Wang X, Lei K. Design, Synthesis, Mode of Action and Herbicidal Evaluation of Quinazolin-4(3H)-one Derivatives Based on Aryloxyphenoxypropionate Motif. Agronomy. 2022; 12(8):1840. https://doi.org/10.3390/agronomy12081840
Chicago/Turabian StyleWang, Chaochao, Ke Chen, Na Li, Shuyue Fu, Pan Li, Lusha Ji, Guoyun Liu, Xuekun Wang, and Kang Lei. 2022. "Design, Synthesis, Mode of Action and Herbicidal Evaluation of Quinazolin-4(3H)-one Derivatives Based on Aryloxyphenoxypropionate Motif" Agronomy 12, no. 8: 1840. https://doi.org/10.3390/agronomy12081840