Utility of 5,5′‐Methylenebis(2‐hydroxybenzaldehyde) – cyanoacetohydrazide Hybrid as Scaffold for the Synthesis of Bis‐Heterocyclic Moieties and Study of Their Insecticidal Activity

Abstract

The cotton leafworm, Spodoptera littoralis Boisd. is a serious pest attacking a wide range of ornamentals and many field crops. It is well documented that some heterocyclic systems have efficient insecticidal activities. So novel hydrazide‐hydrazone namely, N′,N′′′‐((methylenebis(6‐hydroxy‐3,1‐phenylene))bis(methanylylidene))bis(2‐cyanoacetohydrazide) 3 was exploited as a target to synthesize bis‐heterocyclic moieties such as furan, pyridone, coumarin, thiazole and isoxazole, and also some bis‐heteroarylidenes including heterocycles as indole and pyrazole. The chemical structures of the synthesized compounds were established on the basis of elemental analyses and some spectroscopic tools. All the synthesized compounds were screened for the insecticidal efficacy against the 4th larval instar of Spodoptera littoralis (cotton leafworm). Manifestly, the data showed that compounds 9 and 14 possess remarkable potency but the rest of compounds showed no pronounced activity against cotton leafworm.

Synthesis, Antioxidant and Antiproliferative Evaluation, Molecular Docking and DFT Studies of Some Novel Coumarin and Fused Coumarin Derivatives

“…Noteworthy, we exploited the reactivity of compound 3 with various electrophiles and nucleophiles reagents, depending on our previous knowledge and work [40–53] . At this point, heating to reflux 3 with N , N’ ‐dimethylformamide dimethyl acetal (DMF‐DMA) in xylene afforded the predictable enamine derivative 9 .…”

“…Noteworthy, we exploited the reactivity of compound 3 with various electrophiles and nucleophiles reagents, depending on our previous knowledge and work. [40][41][42][43][44][45][46][47][48][49][50][51][52][53] At this point, heating to reflux 3 with N,N'-dimethylformamide dimethyl acetal (DMF-DMA) in xylene afforded the predictable enamine derivative 9. (Scheme 4) The chemical structure of compound 9 was conspicuously supported by spectroscopic data.…”

“…On the other hand, cyanoacetohydrazide plays dramatically an important role as a scaffold in the synthesis of different heterocyclic moieties such as iminocoumarin, pyridone, pyrazole and thiazole rings, etc. [40][41][42][43][44][45][46][47][48][49][50][51][52][53] Due to cyanoacetohydrazide scaffold possessing intriguing functional groups; NH and active methylene groups act as nucleophilic centers, and also cyano group act as an electrophilic center during the reactions.…”

Synthesis and evaluation of larvicidal efficacy against C. pipiens of some new heterocyclic compounds emanated from 2‐cyano‐N′‐(2‐(2,4‐dichlorophenoxy)acetyl)acetohydrazide

“…Intriguingly, the extensive use of cyanoacetohydrizide derivatives dramatically represents an important class for the design and synthesis of various heterocycles by employment the electrophilic and nucleophilic sites which are present in it as reported in our previous work. [17,[19][20][21][22][23][24][25][26][27][28][29] One of the interesting reasons for design of building block containing chlorine motifs is owing to the insecticidal activity of the obtained 2,4dichlorobenzylidenecyanoacetohydrazide derivative which has remarkable potent approximately convergent with LC 50 of methoxyfenozide against cotton leaf worm (Spodoptera littoralis) in the recent our article. [24] Herein, we focused our interest in the laboratory to design and synthesize of 2-cyano-N'-(2-(2,4-dichlorophenoxy)acetyl)acetohydrazide 3.…”

Ultrasonic-induced synthesis of novel diverse arylidenes via Knoevenagel condensation reaction. Antitumor, QSAR, docking and DFT assessment

“…[22][23][24][25][26] So that, cyanoacetohydrazide is a privileged starting molecule for developing possible bioactive agents, and their derivatives represent an important class of heterocyclic compounds, they exhibited a wide spectrum of bioactivity. For example, antitumor, [27][28][29] anti-fungal, 30 anti-inammatory, 31,32 anti-microbial, 33,34 as well as insecticidal 35,36 and corrosion inhibitory activities. 37 Noteworthy, it is well known that the ultrasonic energy has become widely used in pharmaceutical and industrial applications.…”