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

Abstract

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 LC50 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.

Keywords

• novel β-naphthol derivatives
• synthesis
• pesticidal activity
• ryanodine receptor
• structure-activity relationship