Larvicidal activity of substituted chalcones against Aedes aegypti (Diptera: Culicidae) and non‐target organisms

Abstract

BACKGROUND: The expansion of Aedes aegypti (Diptera: Culicidae) population has increased the number of cases of arboviruses, in part due to the inefficiency and toxicity of the chemical control methods available to control this vector. We synthesized 19 chalcone derivatives and examined their activity against Ae. aegypti larvae in order to select larvicidal compounds that are non-toxic to other organisms. RESULTS: Seven chalcone derivatives (3a, 3e, 3f, 6a, 6c, 6d, and 6f) had lethal concentrations of substituted chalcones capable of killing 50% (LC 50) values lower than 100 mg mL −1 at 24 h post-treatment, which is the dose that the World Health Organization recommends for the selection of promising larvicides. The type of substituent added to (E)-1,3-diphenylprop-2-en-1-one (3a) markedly affected the larvicidal activity. Addition of chlorine, bromine and methoxy groups to the aromatic rings reduced the larvicidal activity, while replacement of the Bring (phenyl) by a furan ring significantly increased the larvicidal activity. The furan-chalcone (E)-3-(4-bromophenyl)-1-(furan-2-yl)prop-2-en-1-one (6c) killed Ae. aegypti larvae (LC 50 = 6.66 mg mL −1 ; LC 90 = 9.97 mg mL −1) more effectively than the non-substituted chalcone (3a) (LC 50 = 14.43 mg mL −1 ; LC 90 = 20.96 mg mL −1), and was not toxic to the insect Galleria mellonella, to the protozoan Tetrahymena pyriformis, and to the algae Chorella vulgaris. CONCLUSIONS: The substitution pattern of chalcones influenced their larvicidal activity. In the set of compounds tested, (E)-3-(4-bromophenyl)-1-(furan-2-yl)prop-2-en-1-one (6c) was the most effective larvicide against Ae. aegypti, with no clear signs of toxicity to other animal models. Its mechanism of action and effectiveness under field conditions remain to be determined.

Novel Galactosyl Moiety-Conjugated Furylchalcones Synthesized Facilely Display Significant Regulatory Effect on Plant Growth

“…9−12 Recently, it has been reported that chalcones have been served as novel insecticides to control insect population, such as angular benzofuran chalcones, 13 chemically modified chalcones, 14 the chalcone derivatives kanakugiol, hydroxychalcone and cardamonin, 15 and furan-chalcones. 16 Moreover, the fungistatic and fungicidal effects of chalcones have also been investigated against phytopathogens in greater detail, including geranyl chalcones, 17 chalcone-based strobilurins, 18 dihydrochalcones (mainly phloridzin, sieboldin, trilobatin, and phloretin), 19 vanillin-chalcones, 20 ferrocenyl-chalcones, 21 isobavachalcones, 22 dihydrochromane-chalcones, 23 and isobavachalcones. 24 In contrast, the herbicidal activity of chalcones has been less investigated.…”

In vitro and in vivo evaluation of genotoxicity, cytotoxicity, and protective effects of synthetic chalcones (E)-3-(4-chlorophenyl)-1-phenyl-2-propen-1-one (4-CL) and (E)-3-(3,4-dimethoxyphenyl)-1- phenyl-2-propen-1-one (DMF)

“…The chalcones 4-CL and DMF have been shown to have diverse biological activities and pharmaceutical applications [11][12][13][14][15][16][17][18][19][21][22][23]. However, the toxicogenetic risk information about them is mandatory to ensure their safe use [27,28].…”

“…Recently, according to Chen et al [17], DMF exhibited cardioprotective and potential anticancer effects in mice thought the activation of pro-autophagic transcription factors. The chalcone 4-CL has presented also others activities, such as antioxidant [18], antiprotozoal [19], antinociceptive [20], anti-inflammatory [18], larvicidal [21,22], osteogenic [23], antiplasmodial activity [24] and no neurotoxic effect [25]. According to Sahin et al [26], chalcone 4-CL can be also considered as good candidate for liver cancer therapeutics.…”

Curcumin Derivatives as Potential Mosquito Larvicidal Agents against Two Mosquito Vectors, Culex pipiens and Aedes albopictus

“…The structurally related chalcones have also been investigated as mosquito larvicides and the compound (E)-3-(4-bromophenyl)-1-(furan-2-yl) prop-2-en-1-one exhibited an LC 50 value of 6.66 mg/L at 24 h against Ae. aegypti larvae [36]. Additionally, 28 compounds, chalcones and some derived products, were synthesized and tested for mosquito larvicidal activity against the third instar larvae of Cx.…”