Sustainable Synthesis of Flavonoid Derivatives, QSAR Study and Insecticidal Activity against the Fall Armyworm, Spodoptera frugiperda (Lep.: Noctuidae)

Romanelli, Gustavo Pablo; Virla, Eduardo Gabriel; Duchowicz, Pablo R.; Gaddi, Ana Laura; Ruiz, Diego Manuel; Bennardi, Daniel Oscar; Ortiz, Erlinda V.; Autino, Juan Carlos

doi:10.1021/jf100073j

Cited by 38 publications

(39 citation statements)

References 39 publications

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“…Insecticidal activities of target compounds and positive controls (fipronil, 96% purity and chlorantraniliprole, 95% purity) against Spodoptera frugiperda were tested indoors according to the literature 34 . Each of the test compounds was dissolved in DMSO and diluted to 100 mg L −1 with distilled water containing Tween 80 (0.1%, v/v ).…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and insecticidal activities of novel 5‐substituted 4,5‐dihydropyrazolo[1,5‐a]quinazoline derivatives

Yang

Lai

et al. 2020

Pest Management Science

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BACKGROUND Chemical pesticides are the main measures for pest control, but have caused growing resistance of pests and brought a series of environmental problems. Development of high‐efficient insecticidal molecules with novel scaffolds is therefore particularly urgent. RESULTS Based on a [5 + 1] annulation reaction with 5‐amino‐1H‐phenylpyrazole and dialkyl bromomalonate, 27 novel five‐substituted 4,5‐dihydropyrazolo[1,5‐a]quinazolines were designed following the intermediate derivatization method and synthesized. Bioassay results indicated that most of the test compounds displayed good insecticidal activities against Plutella xylostella, Spodoptera frugiperda, and Solenopsis invicta. In particular, the insecticidal activities of compounds 4a, 4f, and 4m against P. xylostella [median lethal concentration (LC50) values ranged from 3.87 to 5.10 mg L−1] were comparable to that of indoxacarb (LC50 = 4.82 mg L−1). In addition, compounds 4a and 9e showed similar high insecticidal activities against Spodoptera frugiperda (mortality rate = 79.63% and 72.12%) at 100 mg L−1, comparable to that of fipronil (mortality rate: 68.44%); compound 9a showed possible delayed toxicity against Solenopsis invicta (mortality rate: 95.66%) after 5 days of treatment at 1.0 mg L−1. CONCLUSION Due to their high insecticidal activities against P. xylostella, compound 4m, 4a, and 4f could be considered as qualified candidates for novel insecticide. Several other 4,5‐dihydropyrazolo[1,5‐a]quinazolines with relatively high bioactivity, such as compounds 9a and 9e, are also worth further optimization as potential insecticide or anticide candidates.

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Section: Methodsmentioning

confidence: 99%

Design, synthesis, and insecticidal activities of novel 5‐substituted 4,5‐dihydropyrazolo[1,5‐a]quinazoline derivatives

Yang

Lai

et al. 2020

Pest Management Science

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“…The flavonoids have a protector effect from ultraviolet light and microbial damage, and some synthetic derivatives have shown insecticide activity. For example, Romanelli et al [ 27 ] obtained a series of 9 flavonoid derivatives of 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones. Its base structure is shown in Figure 3 .…”

Section: Chemical Insecticidesmentioning

confidence: 99%

Advances in Control Strategies against Spodoptera frugiperda. A Review

et al. 2021

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The strategies for controlling the insect pest Spodoptera frugiperda have been developing over the past four decades; however, the insecticide resistance and the remarkable adaptability of this insect have hindered its success. This review first analyzes the different chemical compounds currently available and the most promising options to control S. frugiperda. Then, we analyze the metabolites obtained from plant extracts with antifeedant, repellent, insecticide, or ovicide effects that could be environmentally friendly options for developing botanical S. frugiperda insecticides. Subsequently, we analyze the biological control based on the use of bacteria, viruses, fungi, and parasitoids against this pest. Finally, the use of sex pheromones to monitor this pest is analyzed. The advances reviewed could provide a wide panorama to guide the search for new pesticidal strategies but focused on environmental sustainability against S. frugiperda.

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“…In this study, the insecticidal activities of the target compounds 8a and 8b and 9a-9t against P. xylostella (thirdinstar Larvae) and S. frugiperda (second-instar larvae) were evaluated using the previously reported methods. [26,27] Meanwhile, chlorantraniliprole was used as a positive control under the same conditions. The results of the preliminary bioassays, as listed in Table 1, indicated that the target compounds 8a and 8b and 9a-9t showed insecticidal activities against P. xylostella at 200 mg/L and 50 mg/L with the values of 0% to 93.64% and 0% to 72.59%, respectively, which were all lower than chlorantraniliprole (mortality rate, 100% and 96.67%, respectively).…”

Section: Insecticidal Activities and Sar Analysismentioning

confidence: 99%

Design, synthesis and insecticidal‐activity evaluation of N‐pyridylpyrazolo‐5‐methyl amines and its derivatives

Yang

Lai

et al. 2020

Journal of Heterocyclic Chem

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In searching for novel insecticidal leads, a series of N-pyridylpyrazolo-5-methyl amines and their derivatives were designed and synthesized. Among the 22 target compounds obtained, bioassays indicated that some of the target compounds exhibited good insecticidal activities against Plutella xylostella (P. xylostella) and Spodoptera frugiperda (S. frugiperda). In particular, compound 9j revealed the best insecticidal activity against P. xylostella, with a LC 50 value of 22.11 mg/L, and compound 9q had the best insecticidal activity against S. frugiperda which with 73.99% of mortality rate at 100 mg/L. Structure-activity relationship (SAR) analysis showed that 4-CF 3 at the position of R 1 linked with N-pyridylpyrazole via amide bond could enhance the insecticidal activity of the target compounds. This study provides valuable clues for the further design and optimization of N-pyridylpyrazole derivatives.

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Sustainable Synthesis of Flavonoid Derivatives, QSAR Study and Insecticidal Activity against the Fall Armyworm, Spodoptera frugiperda (Lep.: Noctuidae)

Cited by 38 publications

References 39 publications

Design, synthesis, and insecticidal activities of novel 5‐substituted 4,5‐dihydropyrazolo[1,5‐a]quinazoline derivatives

Design, synthesis, and insecticidal activities of novel 5‐substituted 4,5‐dihydropyrazolo[1,5‐a]quinazoline derivatives

Advances in Control Strategies against Spodoptera frugiperda. A Review

Design, synthesis and insecticidal‐activity evaluation of N‐pyridylpyrazolo‐5‐methyl amines and its derivatives

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