Synthesis of novel 3/5(3,5)-(di)nitropaeonol hydrazone derivatives as nematicidal agents

Abstract

Eighteen novel 3/5(3,5)-(di)nitropaeonol hydrazone derivatives were prepared, and their structures well characterized by ¹H NMR, HRMS, and mp. Due to the steric hindrance, the substituents on the C = N double bond of all hydrazine compounds (except E/Z = 4/1 for IV-1g, IV-1l, IV-2b, and E/Z = 3/2 for IV-1n, IV-3a) adopted E configuration. Among all compounds, four compounds 2, 4, IV-1j, and IV-1n exhibited potent nematicidal activity than their precursor paeonol, especially 5-nitropaeonol (2) and 3,5-dinitropaeonol (4) displayed the most potent nematicidal activity Heterodera glycines in vivo with LC₅₀ values of 32.3307 and 36.7074 mg/L, respectively.

Graphical abstract

KEYWORDS:

• Paeonol
• structural modification
• hydrazine
• nematicidal activity
• botanical nematicides

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was financially supported by Key Science and Technology Program of Henan Province (Grant No. 202102110068), Young Teacher Funding Program of the Henan Higher School (Grant No. 2020GGJS080), National Natural Science Foundation of China (Grant No. 31901863).