Synthesis and insecticidal activity of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold

Abstract

Abstract Background The diacylhydrazine derivatives have attracted considerable attention in recently years due to their simple structure, low toxicity, and high insecticidal selectivity. As well as 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole is an important scaffold in many insecticidal molecules. In an effort to discover new molecules with good insecticidal activity, a series of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold was synthesized and bio-assayed. Results Bioassays demonstrated that some of the title compounds exhibited favorable insecticidal activities against Helicoverpa armigera and Plutella xylostella. The insecticidal activity of compounds 10g, 10h, and 10w against H. armigera were 70.8, 87.5, and 79.2%, respectively. Compounds 10c, 10e, 10g, 10h, 10i, 10j and 10w showed good larvicidal activity against P. xylostella. In particular, the LC50 values of compounds 10g, 10h, and 10w were 27.49, 23.67, and 28.90 mg L−1, respectively. Conclusions A series of diacylhydrazine derivatives containing a 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole scaffold was synthesized and bio-assayed. The results of insecticidal tests revealed that the synthesized diacylhydrazine derivatives possessed weak to good insecticidal activities against H. armigera and P. xylostella. Compounds 10g, 10h, and 10x showed much higher insecticidal activity than tebufenozide, and exhibited considerable prospects for further optimization. Primary structure–activity relationship revealed that phenyl, 4-fluoro phenyl and four fluorophenyl showed positive influence on their insecticidal activities, and introduction of a heterocyclic ring (pyridine and pyrazole) showed negative impacts on their insecticidal effects.

Keywords

• Diacylhydrazine
• 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole
• Synthesis and insecticidal activity