Design, Synthesis, and Insecticidal Activity of Some Novel Diacylhydrazine and Acylhydrazone Derivatives

Abstract

Abstract:In this study a series of diacylhydrazine and acylhydrazone derivatives were designed and synthesized according to the method of active group combination and the principles of aromatic group bioisosterism. The structures of the novel derivatives were determined on the basis on 1 H-NMR, IR and ESI-MS spectral data. All of the compounds were evaluated for their in vivo insecticidal activity against the third instar larvae of Spodoptera exigua Hiibner, Helicoverpa armigera Hubner, Plutella xyllostella Linnaeus and Pieris rapae Linne, respectively, at a concentration of 10 mg/L. The results showed that all of the derivatives displayed high insecticidal activity. Most of the compounds presented higher insecticidal activity against S. exigua than the reference compounds tebufenozide, metaflumizone and tolfenpyrad, and approximately identical insecticidal activity against H. armigera, P. xyllostella and P. rapae as the references metaflumizone and tolfenpyrad.

Design, Synthesis and 3D‐QSAR of New Quinazolin‐4(3H)‐one Derivatives Containing a Hydrazide Moiety as Potential Fungicides

“…Hydrazide fragments, the important natural nitrogenous substructures that easily form hydrogen bonds with various biological enzymes, are found in many bioactive compounds with antibacterial, anticancer, anticoagulant, anti‐inflammatory, antifungal, antimalarial, antiviral, insecticidal or herbicidal property. In the last decade, the studies on synthesis and agricultural bioactivity of hydrazide derivatives have attracted considerable attentions .…”

“…Strikingly, Zhang et al verified the antifungal mechanism of 3-acylaminoquinazolinone derivatives as chitinase inhibitors, and found a carbonyl group at the N-3 position of quinazolin-4(3H)-one nucleus plays a key role in inhibiting chitinous biosynthesis. [15] Hydrazide fragments, the important natural nitrogenous substructures that easily form hydrogen bonds with various biological enzymes, [20] are found in many bioactive compounds with antibacterial, [21] anticancer, [22] anticoagulant, [23] anti-inflammatory, [24] antifungal, [25] antimalarial, [26] antiviral, [27] insecticidal [28] or herbicidal [29] property. In the last decade, the studies on synthesis and agricultural bioactivity of hydrazide derivatives have attracted considerable attentions.…”

Synthesis, Characterization, and Conformational Study of Acylhydrazones of α,β‐Unsaturated Aldehydes

“…It is well established that azomethine compounds in general and N-acylhydrazones (NAHs) in particular, are very useful in many areas [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18]. Particularly, they have been used as highly effective extractants of several metals [19,20].…”

Formicidal activity of indole derivatives on Atta opaciceps (Borgmeier): Lethal, behavioural and locomotive effects

“…When acetylcholinesterase (AChE) is inhibited, paralysis and death of the insect occur (Barbosa et al, 2012;Santos, Donnici, Costa, & Caixeiro, 2007). Neuroactive activities may also compromise the functioning of sodium channels, disrupting electrical signalling in the nervous system (Soderlund, 2013). Prolonged activation of the sodium channels causes "knockdown" (rapid paralysis) (Dong et al, 2014).…”

“…The discovery of new compounds by synthetic derivation has been successful in the management of important pest insects (Alvarenga et al., ; Lima et al., ; Sun & Zhou, ; Yang, Li, Wu, Liu, & Chang, ) demonstrating that the variation of chemical radicals in the structure of the compound may be responsible for differences observed in their activities. This relationship between structure and activity may indicate compounds more favourable to biological action and help in the optimization of insecticides by including, for example, characteristics that have a low environmental impact.…”