Synthesis and evaluation of novel 1-(((6-substitutedbenzo[ d ]thiazol-2-yl)amino)(heteroaryl)methyl)naphthalen-2-ol as pesticidal agents.
Junfeng ShangYuxin LiNa YangLixia XiongBao-Lei WangPublished in: Journal of enzyme inhibition and medicinal chemistry (2022)
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.