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

• Published in: Journal of enzyme inhibition and medicinal chemistry 2022-12, Vol.37 (1), p.641-651
• Main Authors: Shang, Junfeng, Li, Yuxin, Yang, Na, Xiong, Lixia, Wang, Baolei
• Format: Article
• Language: English
• Subjects: Agricultural production; Agrochemicals; Bioassays; Calcium imaging; Chromatography; Enzymes; Laboratories; Lethality; Novel β-naphthol derivatives; Organic chemistry; pesticidal activity; Research Paper; ryanodine receptor; Solvents; structure-activity relationship; synthesis
• ISSN: 1475-6366; 1475-6374
• DOI: 10.1080/14756366.2022.2032687

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.