Discovery of Novel Isoxazoline Compounds that Incorporate a <i>para</i>-Diamide Moiety as Potential Insecticidal Agents against Fall Armyworm (<i>Spodoptera frugiperda</i>)

Jiang, Biaobiao; Li, Fangyi; Feng, Di; Wei, Wuran; Luo, Yuqin; He, Siqi; Dong, Yawen; Hu, Deyu

doi:10.1021/acs.jafc.3c00351

Cited by 4 publications

(2 citation statements)

References 36 publications

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“…After that, the nine isoxazoline-type GABA insecticides were discovered gradually (Figure ). Some studies , reported that the modified isoxazoline compounds exhibited excellent insecticidal activities.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Insecticidal Activity, and SAR of Aryl Isoxazoline Derivatives Containing Pyrazole-5-carboxamide Motif

Zhong,

Sun,

Han

et al. 2023

J. Agric. Food Chem.

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It is important to develop new insecticides with a new mode of action because of increasing pesticide resistance. In this study, a series of novel aryl isoxazoline derivatives containing the pyrazole-5-carboxamide motif were designed and synthesized. Their structures were confirmed by 1 H NMR, 13 C NMR, and HRMS. Bioassays indicated that the 24 compounds synthesized possessed excellent insecticidal activity against Mythimna separate and no activity against Aphis craccivora and Tetranychus cinnabarinus. Among these aryl isoxazoline derivatives, 3-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydrozol-3-yl)-N-(4fluorophenyl)-1-methyl-1H-pyrazole-5-carboxamide (IA-8) had the best insecticidal activity against M. separate, which is comparable with the positive control fluralaner. The molecular docking results of compound IA-8 and fluralaner with the GABA model demonstrated the same docking mode between compound IA-8 and positive control fluralaner in the active site of GABA. Molecular structure comparisons and ADMET analysis can potentially be used to design more active compounds. The structure−activity relationships are also discussed. This work provided an excellent insecticide for further optimization.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Insecticidal Activity, and SAR of Aryl Isoxazoline Derivatives Containing Pyrazole-5-carboxamide Motif

Zhong,

Sun,

Han

et al. 2023

J. Agric. Food Chem.

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“… However, they are approved only in limited countries and are not widely available worldwide. Therefore, further exploration of isoxazolines for the development of efficient insecticides with biosafe for nontarget organisms and environmentally friendly has attracted widespread attention. − …”

Section: Introductionmentioning

confidence: 99%

Rational Design of Insecticidal Isoxazolines Containing Sulfonamide or Sulfinamide Structure as Antagonists of GABA Receptors with Reduced Toxicities to Honeybee and Zebrafish

Yang,

Tang,

et al. 2023

J. Agric. Food Chem.

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To develop highly effective, nontarget organism-friendly insecticides based on the isoxazoline scaffold, we rationally designed and synthesized 25 isoxazoline derivatives containing sulfonamides and sulfinamides. Their insecticidal activities against the diamondback moth (Plutella xylostella), fall armyworm (Spodoptera frugiperda), beet armyworm (Spodoptera exigua), and Spodoptera litura Fabricius (S. litura) were evaluated. The trifluoromethyl sulfinamide-containing compound 7w displayed excellent activities with LC50 values being 0.09, 0.84, 0.87, and 0.68 mg/L against P. xylostella, S. frugiperda, S. exigua, and S. litura, respectively, which were superior to fluxametamide (LC50 = 0.09, 1.24, 1.10, and 0.65 mg/L, respectively) and maintained at the same order of magnitude LC50 values as fluralaner (LC50 = 0.02, 0.17, 0.12, and 0.19 mg/L, respectively). Importantly, compound 7w showed a medium toxicity level of acute toxicity to honeybee (LD50 = 2.22 μg/adult), which is significantly lower than the fluralaner (high toxicity level, LD50 = 0.09 μg/adult). Acute toxicity experiments with zebrafish (Danio rerio) indicated that compound 7w was safe with the LC50 value being 42.4 mg/L (low toxicity level). Furthermore, electrophysiological experiments and molecular docking studies preliminarily verified that compound 7w acts on the insect GABA receptor, and the theoretical calculations explained that the sulfinamide structure may play an important role in exhibiting biological activities. The above results suggest that compound 7w could be employed as a potentially highly effective, environmentally friendly insecticide to control multiple agricultural pests.

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Design, synthesis and insecticidal activity of novel Isoxazoline Acylhydrazone compounds

Li,

Yin

et al. 2023

Pest Management Science

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BACKGROUNDNowadays, the diamondback moth has ascended to become one of the most formidable pests plaguing cruciferous vegetables. Consequently, the exigency for the development of efficacious pesticide candidates for crop protection has never been more paramount. In response to this pressing need, this study presents a compendium of novel isoxazoline derivatives, incorporating acylhydrazone moieties, synthesized with the express purpose of serving as potential insecticides.RESULTSThe structures of these derivatives were confirmed using Proton nuclear magnetic resonance (1H NMR), Carbon‐13 nuclear magnetic resonance (13C NMR), and high‐resolution mass spectrometry (HR‐MS). Most of these derivatives demonstrated effective insecticidal activities against Plutella xylostella. Notably, compound E3 exhibited exceptional insecticidal activity against Plutella xylostella (LC50 = 0.19 mg L−1), surpassing the effectiveness of ethiprole (LC50 = 3.28 mg L−1), and comparable to that of fluxametamide (LC50 = 0.22 mg L−1). Interestingly, compound E3 also displayed potent insecticidal activity against Pyrausta nubilalis (LC50 = 0.182 mg L−1) and Chilo suppressalis (LC50 = 0.64 mg L−1), and the LC50 values of fluxametamide were 0.23 mg L−1 (P. nubilalis) and 2.26 mg L−1 (C. suppressalis), respectively. The molecular docking results revealed that the compound E3 can form a hydrogen bond and two Pi‐Pi bonds with the active sites of GABA receptors. In addition, the DFT calculations were also performed to study the relationship between insecticidal activities. The structure–activity relationships suggested that the identity of the R substituent was crucial for their pesticidal activities.CONCLUSIONThe results of the present study suggest that isoxazoline acylhydrazone derivatives could be promising candidates against P. xylostella and other Lepidopteran pests. © 2023 Society of Chemical Industry.

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Discovery of Novel Isoxazoline Compounds that Incorporate a para-Diamide Moiety as Potential Insecticidal Agents against Fall Armyworm (Spodoptera frugiperda)

Cited by 4 publications

References 36 publications

Design, Synthesis, Insecticidal Activity, and SAR of Aryl Isoxazoline Derivatives Containing Pyrazole-5-carboxamide Motif

Design, Synthesis, Insecticidal Activity, and SAR of Aryl Isoxazoline Derivatives Containing Pyrazole-5-carboxamide Motif

Rational Design of Insecticidal Isoxazolines Containing Sulfonamide or Sulfinamide Structure as Antagonists of GABA Receptors with Reduced Toxicities to Honeybee and Zebrafish

Design, synthesis and insecticidal activity of novel Isoxazoline Acylhydrazone compounds

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