Synthesis, Characterization, and Biochemical Impacts of Some New Bioactive Sulfonamide Thiazole Derivatives as Potential Insecticidal Agents against the Cotton Leafworm, Spodoptera littoralis

Abstract

A novel series of anticipated biologically active heterocyclic compounds, such as pyrazole, thiazole, pyridine, acrylamide, thiophene, triazolo­[1,5-a]­pyrimidine, imidazolidine, aminopyrazole, pyrazolo­[5,1-c]­[1,2,4]­triazine, triazolo­[4,3-a]­pyrimidine, benzo­[4,5]­imidazo­[1,2-a]­pyrimidine, pyrido­[2′,3′:3,4]­pyrazolo­[5,1-c]­[1,2,4]­triazine, isoxazole, benzo­[4,5]­imidazo­[2,1-c]­[1,2,4]­triazine, pyrimidine, pyrido­[2′,3′:3,4]­pyrazolo­[1,5-a]­pyrimidine, pyrano­[2,3-d]­pyrimidine, and chromene derivatives, incorporating a sulfonamide-bearing thiazole moiety suitable to utilize as insecticidal agents were synthesized via a versatile, readily accessible cyanoacetanilide, 2-cyano-N-(4-(N-(thiazol-2-yl)­sulfamoyl)­phenyl)­acetamide (1).The structures of the newly synthesized compounds were elucidated by IR, MS, 1H NMR, 13C NMR, distortionless enhancement by polarization transfer (DEPT), 1H–1H correlation spectroscopy (COSY), heteronuclear multiple bond correlation (HMBC), and heteronuclear single quantum coherence (HSQC) spectral analysis. Toxicological and biochemical parameters and biological aspects of the demonstrated compounds of the synthesized products against the cotton leafworm, Spodoptera littoralis, under laboratory conditions were also investigated. Regarding the determined LC50 and LC90 values, sulfonamides bearing a thiazole moiety, 16a, 8, 28, and 31b, showed the most potent toxic effects with LC50 values of 49.04, 62.66, 78.62, and 94.90 ppm, respectively, and toxicity index of 100%, 78.26%, 62.38%, and 51.68%, respectively.

One‐Pot Synthesis and Anticancer Activity of Novel Pyrazole Hybrids

“…Novel fifteen pyrazole hybrids (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) were synthesized in good yields (68-98 %) via a one-pot reaction of thiocarbonyldihydrazide (1) and ethyl 3-phenyl-3-oxopropanoate (2) with appropriate carbonyl reagents (e. g., aromatic and heterocyclic aldehydes and ketones) and carbohydrazides (e. g., benzohydrazide, cyanoacetohydrazide, and malonohydrazide). The structures of the pyrazole hybrids (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) were confirmed with IR, MS, 1 HNMR, 13 CNMR spectral analysis, and elemental analysis. All pyrazoles were tested for their cytotoxicity against different breast cancer cell lines (e. g., MCF-7, MDA-MB-231, and 4T1) as well as HepG2 liver cancer cells.…”

“…[5] Accordingly, several synthetic pyrazol-based drugs were developed with potential medicinal (e. g., Viagra (VI), and Celebrex (VII)), pesticidal (e. g., Cyenopyrafen (VIII)), and insecticidal (e. g., Tebufenpyrad (IX)) applications. [5][6][7] Furthermore, several pyrazoles are used as chelating ligands for a variety of metal ions. [8] Moreover, they are also used as versatile synthons for combinatorial chemistry for condensed heterocyclic constructions.…”

“…For instance, Withasomnine (I) isolated from nightshades showed anti‐inflammatory and analgesic activities, L‐α‐amino‐β‐(pyrazolyl‐N)‐propanoic acid ( II ) isolated from watermelon exhibited antidiabetic activity, and pyrazofurin ( III ) and formycin A ( IV ) isolated from Streptomyces candidus displayed anticancer and antiviral activities [5] . Accordingly, several synthetic pyrazol‐based drugs were developed with potential medicinal (e. g., Viagra ( VI ), and Celebrex ( VII )), pesticidal (e. g., Cyenopyrafen ( VIII )), and insecticidal (e. g., Tebufenpyrad ( IX )) applications [5–7] . Furthermore, several pyrazoles are used as chelating ligands for a variety of metal ions [8] .…”

Design, Synthesis and Fungicidal Activity of Novel 2‐aryl‐thiazole Derivatives Containing Saccharin Motif

“…Moreover, by virtue of prominent bioactivities of various thiazole derivatives, thiazole ring has drawn tremendous attention in agrochemistry. [11][12][13][14][15] In recent years, ample compounds containing thiazole ring as building block have become commercial products, such as ethaboxam, [16] trifluzamide, [17] and TCMTB [18] (Figure 1a). Diimide building blocks (pharmacophores) occupy a status of equal importance for the structure of fungicides, and have yielded in the synthesis and commercialization of captan, [19] captafol, and folpet [20] (Figure 1b).…”

“…Thiazole matrices play a prominent role in drug design, [8–10] as they feature high flexibility in location of substituents, i. e. substituents can be introduced at positions C‐2, C‐4 and, C‐5. Moreover, by virtue of prominent bioactivities of various thiazole derivatives, thiazole ring has drawn tremendous attention in agrochemistry [11–15] . In recent years, ample compounds containing thiazole ring as building block have become commercial products, such as ethaboxam, [16] trifluzamide, [17] and TCMTB [18] (Figure 1a).…”