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.

Graphical abstract

Keywords:

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

Acknowledgement

The authors express heartfelt appreciation to Dr. Shorena Gelozia for the kind linguistic modification of this article. Dedicated to the 60th anniversary of Institute of Elemento-Organic Chemistry (Nankai University).

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This study was financially supported by the National Natural Science Foundation of China [Nos. 21772103 and 22077070], the Open Fund of Key Laboratory of Study and Discovery of Small Targeted Molecules of Hunan Province [2019CG04] and the National Key Research and Development Program of China [No. 2017YFD0200505].