Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

Abstract

A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L⁻¹ in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L⁻¹. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further.

Graphical Abstract

Keywords:

• 1,2,3-benzotriazin-4-one
• 4,5-dihydrothiazole-2-thiol
• M. incognita
• nematicidal activity

Acknowledgments

We are very thankful to Dr. Bingli Gao and his coworkers in Huzhou Modern Agricultural Biotechnology Innovation Center, Chinese Academy of Sciences, China, for the nematicidal evaluation. We are very thankful to He Nan Metab BioPharma Co., Ltd. for providing the test of X-ray.

Additional information

Funding

This work was financially supported by National Natural Science Foundation of China (21672061), National Key Research Program of China (2018YFD0200105, 2017YFD0200505). This work was also supported by the Fundamental Research Funds for the Central Universities.