{"title":"针对黑僵菌的吡喃并[3,2-c]吡啶酮的设计、合成、杀线虫评价和分子对接研究","authors":"Neelam Yadav, Ravi Kumar, Sarita Sangwan, Vidhi Dhanda, Reena Rani, Sheetu Devi, Anil Duhan, Jayant Sindhu, Sonu Chauhan, Vinod Kumar Malik, Saroj Yadav, Prakash Banakar","doi":"10.1021/acs.jafc.4c00103","DOIUrl":null,"url":null,"abstract":"<p><p>Root-knot nematodes pose a serious threat to crops by affecting production and quality. Over a period of time, substantial work has been done toward the development of effective and environmentally benign nematicidal compounds. However, due to the inefficiencies of previously reported synthetics in achieving the target of safe, selective, and effective treatment, it is necessary to develop new efficacious and safer nematicidal agents considering human health and environment on top priority. This work aims to highlight the efficient and convenient l-proline catalyzed synthesis of pyrano[3,2-<i>c</i>]pyridone and their use as potential nematicidal agents. <i>In vitro</i> results of larval mortality and egg hatching inhibition revealed maximum nematicidal activity against <i>Meloidogyne incognita</i> from compounds <b>15b</b>, <b>15m</b>, and <b>15w</b> with LC<sub>50</sub> values of 28.8, 46.8, and 49.18 μg/mL at 48 h, respectively. Under similar conditions, pyrano[3,2-<i>c</i>]pyridones derivatives <b>15b</b> (LC<sub>50</sub> = 28.8 μg/mL) was found at par with LC<sub>50</sub> (26.92 μg/mL) of commercial nematicide carbofuran. The <i>in vitro</i> results were further validated with <i>in silico</i> studies with the most active compound <b>15b</b> nematicidal within the binding to the pocket of acetylcholine esterase (AChE). In docking, binding free energy values for compound <b>15b</b> were found to be -6.90 kcal/mol. Results indicated that pyrano[3,2-<i>c</i>]pyridone derivatives have the potential to control <i>M. incognita</i>.</p>","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":null,"pages":null},"PeriodicalIF":5.7000,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Design, Synthesis, Nematicidal Evaluation, and Molecular Docking Study of Pyrano[3,2-<i>c</i>]pyridones against <i>Meloidogyne incognita</i>.\",\"authors\":\"Neelam Yadav, Ravi Kumar, Sarita Sangwan, Vidhi Dhanda, Reena Rani, Sheetu Devi, Anil Duhan, Jayant Sindhu, Sonu Chauhan, Vinod Kumar Malik, Saroj Yadav, Prakash Banakar\",\"doi\":\"10.1021/acs.jafc.4c00103\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Root-knot nematodes pose a serious threat to crops by affecting production and quality. Over a period of time, substantial work has been done toward the development of effective and environmentally benign nematicidal compounds. However, due to the inefficiencies of previously reported synthetics in achieving the target of safe, selective, and effective treatment, it is necessary to develop new efficacious and safer nematicidal agents considering human health and environment on top priority. This work aims to highlight the efficient and convenient l-proline catalyzed synthesis of pyrano[3,2-<i>c</i>]pyridone and their use as potential nematicidal agents. <i>In vitro</i> results of larval mortality and egg hatching inhibition revealed maximum nematicidal activity against <i>Meloidogyne incognita</i> from compounds <b>15b</b>, <b>15m</b>, and <b>15w</b> with LC<sub>50</sub> values of 28.8, 46.8, and 49.18 μg/mL at 48 h, respectively. Under similar conditions, pyrano[3,2-<i>c</i>]pyridones derivatives <b>15b</b> (LC<sub>50</sub> = 28.8 μg/mL) was found at par with LC<sub>50</sub> (26.92 μg/mL) of commercial nematicide carbofuran. The <i>in vitro</i> results were further validated with <i>in silico</i> studies with the most active compound <b>15b</b> nematicidal within the binding to the pocket of acetylcholine esterase (AChE). In docking, binding free energy values for compound <b>15b</b> were found to be -6.90 kcal/mol. Results indicated that pyrano[3,2-<i>c</i>]pyridone derivatives have the potential to control <i>M. incognita</i>.</p>\",\"PeriodicalId\":41,\"journal\":{\"name\":\"Journal of Agricultural and Food Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":5.7000,\"publicationDate\":\"2024-07-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Agricultural and Food Chemistry\",\"FirstCategoryId\":\"97\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.jafc.4c00103\",\"RegionNum\":1,\"RegionCategory\":\"农林科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"AGRICULTURE, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Agricultural and Food Chemistry","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1021/acs.jafc.4c00103","RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"AGRICULTURE, MULTIDISCIPLINARY","Score":null,"Total":0}
Design, Synthesis, Nematicidal Evaluation, and Molecular Docking Study of Pyrano[3,2-c]pyridones against Meloidogyne incognita.
Root-knot nematodes pose a serious threat to crops by affecting production and quality. Over a period of time, substantial work has been done toward the development of effective and environmentally benign nematicidal compounds. However, due to the inefficiencies of previously reported synthetics in achieving the target of safe, selective, and effective treatment, it is necessary to develop new efficacious and safer nematicidal agents considering human health and environment on top priority. This work aims to highlight the efficient and convenient l-proline catalyzed synthesis of pyrano[3,2-c]pyridone and their use as potential nematicidal agents. In vitro results of larval mortality and egg hatching inhibition revealed maximum nematicidal activity against Meloidogyne incognita from compounds 15b, 15m, and 15w with LC50 values of 28.8, 46.8, and 49.18 μg/mL at 48 h, respectively. Under similar conditions, pyrano[3,2-c]pyridones derivatives 15b (LC50 = 28.8 μg/mL) was found at par with LC50 (26.92 μg/mL) of commercial nematicide carbofuran. The in vitro results were further validated with in silico studies with the most active compound 15b nematicidal within the binding to the pocket of acetylcholine esterase (AChE). In docking, binding free energy values for compound 15b were found to be -6.90 kcal/mol. Results indicated that pyrano[3,2-c]pyridone derivatives have the potential to control M. incognita.
期刊介绍:
The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.