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Eighteen novel 3/5(3,5)-(di)nitropaeonol hydrazone derivatives were prepared, and their structures well characterized by  1 H 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 LC 50  values of 32.3307 and 36.7074 mg/L, respectively.

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