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Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents

To discover new agrochemicals with prominent pesticidal properties, a series of novel β-naphthol derivatives containing benzothiazolylamino and various heteroaryl groups (8a-q) were efficiently synthesised via Betti reaction. The bioassay results showed that most of the synthesised compounds exhibit...

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Autores principales: Shang, Junfeng, Li, Yuxin, Yang, Na, Xiong, Lixia, Wang, Baolei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Taylor & Francis 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8797731/
https://www.ncbi.nlm.nih.gov/pubmed/35086409
http://dx.doi.org/10.1080/14756366.2022.2032687
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author Shang, Junfeng
Li, Yuxin
Yang, Na
Xiong, Lixia
Wang, Baolei
author_facet Shang, Junfeng
Li, Yuxin
Yang, Na
Xiong, Lixia
Wang, Baolei
author_sort Shang, Junfeng
collection PubMed
description To discover new agrochemicals with prominent pesticidal properties, a series of novel β-naphthol derivatives containing benzothiazolylamino and various heteroaryl groups (8a-q) were efficiently synthesised via Betti reaction. The bioassay results showed that most of the synthesised compounds exhibited favourable insecticidal potentials, particularly towards oriental armyworm (50–100% at 200 mg·L(−1)) and diamondback moth (50–95% at 10 mg·L(−1)). Compounds 8 b, 8f, 8 g, 8j, 8k, 8n, and 8o possessed LC(50) values of 0.0988–5.8864 mg·L(−1) against diamondback moth. Compounds 8i, 8 l, and 8 m also displayed lethality rates of 30–90% against spider mite at the concentration of 100 mg·L(−1). Overall, some compounds could be considered as new insecticidal/acaricidal leading structures for further investigation. The calcium imaging experiments revealed that 8 h, 8i, and viii could activate the release of calcium ions in insect (M. separata) central neurons at a higher concentration (50 mg·L(−1)). The SAR analysis provided valuable information for further structural modifications.
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spelling pubmed-87977312022-01-29 Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents Shang, Junfeng Li, Yuxin Yang, Na Xiong, Lixia Wang, Baolei J Enzyme Inhib Med Chem Research Paper To discover new agrochemicals with prominent pesticidal properties, a series of novel β-naphthol derivatives containing benzothiazolylamino and various heteroaryl groups (8a-q) were efficiently synthesised via Betti reaction. The bioassay results showed that most of the synthesised compounds exhibited favourable insecticidal potentials, particularly towards oriental armyworm (50–100% at 200 mg·L(−1)) and diamondback moth (50–95% at 10 mg·L(−1)). Compounds 8 b, 8f, 8 g, 8j, 8k, 8n, and 8o possessed LC(50) values of 0.0988–5.8864 mg·L(−1) against diamondback moth. Compounds 8i, 8 l, and 8 m also displayed lethality rates of 30–90% against spider mite at the concentration of 100 mg·L(−1). Overall, some compounds could be considered as new insecticidal/acaricidal leading structures for further investigation. The calcium imaging experiments revealed that 8 h, 8i, and viii could activate the release of calcium ions in insect (M. separata) central neurons at a higher concentration (50 mg·L(−1)). The SAR analysis provided valuable information for further structural modifications. Taylor & Francis 2022-01-27 /pmc/articles/PMC8797731/ /pubmed/35086409 http://dx.doi.org/10.1080/14756366.2022.2032687 Text en © 2022 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. https://creativecommons.org/licenses/by/4.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) ), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Paper
Shang, Junfeng
Li, Yuxin
Yang, Na
Xiong, Lixia
Wang, Baolei
Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
title Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
title_full Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
title_fullStr Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
title_full_unstemmed Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
title_short Synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
title_sort synthesis and evaluation of novel 1-(((6-substitutedbenzo[d]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents
topic Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8797731/
https://www.ncbi.nlm.nih.gov/pubmed/35086409
http://dx.doi.org/10.1080/14756366.2022.2032687
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