Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes
Chemo-selective heterogeneous catalytic hydrogenation was employed to synthesise 6-amino-N-methyl-2-quinolone (AMQ) and 6-amino-N-ethyl-2-quinolone (AEQ) to establish its structure-activity relationship (SAR) by 1H NMR,13C NMR, FT-IR, LC-MS/MS. AMQ (MIC = 18.2, 16.5 mg/mL) and AEQ (MIC = 19.2, 20.5 ...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2023-12-01
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| Series: | Food Chemistry Advances |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772753X23003532 |
| _version_ | 1827576439951589376 |
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| author | Swagata Mandal Rajib Karmakar Inul Ansary Dipak Kumar Hazra Rajlakshmi Poi Goutam Mandal Sudip Bhattacharyya |
| author_facet | Swagata Mandal Rajib Karmakar Inul Ansary Dipak Kumar Hazra Rajlakshmi Poi Goutam Mandal Sudip Bhattacharyya |
| author_sort | Swagata Mandal |
| collection | DOAJ |
| description | Chemo-selective heterogeneous catalytic hydrogenation was employed to synthesise 6-amino-N-methyl-2-quinolone (AMQ) and 6-amino-N-ethyl-2-quinolone (AEQ) to establish its structure-activity relationship (SAR) by 1H NMR,13C NMR, FT-IR, LC-MS/MS. AMQ (MIC = 18.2, 16.5 mg/mL) and AEQ (MIC = 19.2, 20.5 mg/mL), were more effective against Aspergillus niger and Aspergillus flavous. Both were tested on tomato (Solanum lycopersicum L.) plants to assess residual profiles, dissipation patterns, and yield effects. Acetonitrile and methanol (9.5:0.5, v/v), and modified buffer QuEChERS were used for extraction and analysed by LC-MS/MS. For AMQ, LOD and LOQ were 0.0065 and 0.017 mg kg−1, respectively, whereas, for AEQ, 0.0031 and 0.017 mg kg−1. The 5-point calibration curves of both compounds were constructed with R2 in the range of 0.99. Average recoveries at LOQ and higher ranged from 82.50 -114.27%. According to first-order kinetics, the half-lives (T1/2) for the T1 and T2 of AMQ were 2.11, and 2.34 days, and for AEQ were 1.66 and 2.13 days, respectively. Estimated pre-harvest intervals (PHIs) for AMQ and AEQ were 8,6 days (T1), and 11,10 days (T2) respectively. Their application enhanced fresh tomato production 21.36–26.55%. Developed compounds have excellent in vitro and in vivo fungicidal action and could treat plant fungal infections. |
| first_indexed | 2024-03-08T21:10:33Z |
| format | Article |
| id | doaj.art-8b22616ac0d74eec87f11defab6d2c30 |
| institution | Directory Open Access Journal |
| issn | 2772-753X |
| language | English |
| last_indexed | 2024-03-08T21:10:33Z |
| publishDate | 2023-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Food Chemistry Advances |
| spelling | doaj.art-8b22616ac0d74eec87f11defab6d2c302023-12-22T05:35:21ZengElsevierFood Chemistry Advances2772-753X2023-12-013100532Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoesSwagata Mandal0Rajib Karmakar1Inul Ansary2Dipak Kumar Hazra3Rajlakshmi Poi4Goutam Mandal5Sudip Bhattacharyya6Department of Chemistry, The University of Burdwan, Burdwan 713104, India; All India Network Project on Pesticide Residues, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Kalyani, Nadia, West Bengal, India; Corresponding authors.All India Network Project on Pesticide Residues, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Kalyani, Nadia, West Bengal, India; Corresponding authors.Department of Chemistry, The University of Burdwan, Burdwan 713104, India; Corresponding authors.All India Network Project on Pesticide Residues, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Kalyani, Nadia, West Bengal, IndiaAll India Network Project on Pesticide Residues, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Kalyani, Nadia, West Bengal, IndiaAll India Network Project on Pesticide Residues, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Kalyani, Nadia, West Bengal, India; AICRP on MAP & Betelvine, Department of Plant Pathology, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Mohanpur-741252, Nadia, West Bengal, IndiaAll India Network Project on Pesticide Residues, Directorate of Research, Bidhan Chandra Krishi Viswavidyalaya, Kalyani, Nadia, West Bengal, IndiaChemo-selective heterogeneous catalytic hydrogenation was employed to synthesise 6-amino-N-methyl-2-quinolone (AMQ) and 6-amino-N-ethyl-2-quinolone (AEQ) to establish its structure-activity relationship (SAR) by 1H NMR,13C NMR, FT-IR, LC-MS/MS. AMQ (MIC = 18.2, 16.5 mg/mL) and AEQ (MIC = 19.2, 20.5 mg/mL), were more effective against Aspergillus niger and Aspergillus flavous. Both were tested on tomato (Solanum lycopersicum L.) plants to assess residual profiles, dissipation patterns, and yield effects. Acetonitrile and methanol (9.5:0.5, v/v), and modified buffer QuEChERS were used for extraction and analysed by LC-MS/MS. For AMQ, LOD and LOQ were 0.0065 and 0.017 mg kg−1, respectively, whereas, for AEQ, 0.0031 and 0.017 mg kg−1. The 5-point calibration curves of both compounds were constructed with R2 in the range of 0.99. Average recoveries at LOQ and higher ranged from 82.50 -114.27%. According to first-order kinetics, the half-lives (T1/2) for the T1 and T2 of AMQ were 2.11, and 2.34 days, and for AEQ were 1.66 and 2.13 days, respectively. Estimated pre-harvest intervals (PHIs) for AMQ and AEQ were 8,6 days (T1), and 11,10 days (T2) respectively. Their application enhanced fresh tomato production 21.36–26.55%. Developed compounds have excellent in vitro and in vivo fungicidal action and could treat plant fungal infections.http://www.sciencedirect.com/science/article/pii/S2772753X230035326-amino-N-methyl-2-quinolone6-amino-N-ethyl-2-quinoloneLODLOQFungicides |
| spellingShingle | Swagata Mandal Rajib Karmakar Inul Ansary Dipak Kumar Hazra Rajlakshmi Poi Goutam Mandal Sudip Bhattacharyya Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes Food Chemistry Advances 6-amino-N-methyl-2-quinolone 6-amino-N-ethyl-2-quinolone LOD LOQ Fungicides |
| title | Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes |
| title_full | Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes |
| title_fullStr | Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes |
| title_full_unstemmed | Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes |
| title_short | Assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes |
| title_sort | assessing residues of newly synthesized quinolone derivatives as antifungals for disease management and consumer safety in tomatoes |
| topic | 6-amino-N-methyl-2-quinolone 6-amino-N-ethyl-2-quinolone LOD LOQ Fungicides |
| url | http://www.sciencedirect.com/science/article/pii/S2772753X23003532 |
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