New lead discovery of insect growth regulators based on the scaffold hopping strategy

Jiang, Biaobiao; Guo, Bingbo; Cui, Jialin; Dong, Yawen; Cui, Li; Zhang, Li; Yang, Qing; Yang, Xinling

doi:10.1016/j.bmcl.2020.127500

Cited by 13 publications

(16 citation statements)

References 23 publications

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“…Pyrazole acid 4 was obtained by a saponification reaction of compound 3 as previously described. , The ester was saponified using a solution of 3 (11.57 mmol), which was combined with an aliquot of 4 mol/L NaOH (34.70 mmol). The mixture was stirred at 80 °C.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Insecticidal Activity of Novel Isoxazoline Compounds That Contain Meta-diamides against Fall Armyworm (Spodoptera frugiperda)

Jiang

Feng

et al. 2023

J. Agric. Food Chem.

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Fall armyworm (Spodoptera frugiperda) is a major migratory pest around the entire world that causes severe damage to agriculture. We designed and synthesized a series of novel isoxazoline derivatives based on the previously discovered active compound H13 to find new and effective candidates against S. frugiperda. Most of them showed excellent insecticidal activity. In addition, a three-dimensional quantitative structure–activity relationship model was established, and compound F32 was designed and synthesized based on the results. The bioassay result showed that compound F32 exhibited excellent activity against S. frugiperda (LC50 = 3.46 mg/L), which was substantially better than that of the positive control fipronil (LC50 = 78.8 mg/L). Furthermore, an insect γ-aminobutyric acid (GABA) enzyme-linked immunosorbent assay indicated that F32 can upregulate the content of GABA in insects in a manner similar to that of fipronil. Molecular docking showed that the hydrophobic effect and hydrogen-bond interactions are vital factors between the binding of F32 and receptors. All of these results suggest that compound F32 could be employed as a novel isoxazoline lead compound to control S. frugiperda.

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Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Insecticidal Activity of Novel Isoxazoline Compounds That Contain Meta-diamides against Fall Armyworm (Spodoptera frugiperda)

Jiang

Feng

et al. 2023

J. Agric. Food Chem.

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“…Intermediate D (23.20 mmol) was dissolved in 20 mL of anhydrous ethanol solution, and sodium hydroxide (34.70 mmol) aqueous solution was added, reflux stirring reaction at 80 °C for 2 h, the reaction solution was evaporated on a rotary evaporator under reduced pressure to remove ethanol and some water, and 60 mL of ice water was poured into the mixture. The solution pH was adjusted to 3–4 with concentrated hydrochloric acid, the solid was filtered through a Büchner funnel, and the filter cake was dried to obtain intermediate E . , …”

Section: Methodsmentioning

confidence: 99%

“…31,32 Preparation Method of Intermediate E. Intermediate D (23.20 mmol) was dissolved in 20 mL of anhydrous ethanol solution, and sodium hydroxide (34.70 mmol) aqueous solution was added, reflux stirring reaction at 80 °C for 2 h, the reaction solution was evaporated on a rotary evaporator under reduced pressure to remove ethanol and some water, and 60 mL of ice water was poured into the mixture. The solution pH was adjusted to 3−4 with concentrated hydrochloric acid, the solid was filtered through a Buchner funnel, and the filter cake was dried to obtain intermediate E. 33,34 Preparation of Target Compounds L1-L37. Compound E (0.72 mmol) and thionyl chloride (21.6 mmol) were added to a 50 mL three-necked flask, one drop of DMF was added under stirring, and the solution gradually became clarified.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Discovery of Novel Isoxazoline Derivatives Containing Diaryl Ether against Fall Armyworms

Feng

Jiang

et al. 2023

J. Agric. Food Chem.

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With the continuous evolution of insect resistance, it is a tremendous challenge to control the fall armyworm (Spodoptera frugiperda) with traditional insecticides. To solve this pending issue, a series of novel isoxazoline derivatives containing diaryl ether structures were designed and synthesized, and most of the target compounds exhibited excellent insecticidal activity. Based on the three-dimensional quantitative structure−activity relationship (3D-QSAR) model analysis, we further optimized the molecular structure with compound L35 obtained and tested for its activity. Compound L35 (LC 50 = 1.69 mg/L) exhibited excellent insecticidal activity against S. frugiperda, which was better than those of commercial fipronil (LC 50 = 70.78 mg/L) and indoxacarb (LC 50 = 5.37 mg/L). The enzyme-linked immunosorbent assay showed that L35 could upregulate the levels of GABA in insects. In addition, molecular docking and transcriptomic results also indicated that compound L35 may affect the nervous system of S. frugiperda by acting on GABA receptors. Notably, through high-performance liquid chromatography (HPLC), we were able to obtain the two enantiomers of compound L35, and the insecticidal activity test revealed that S-(+)-L35 was 44 times more active than R-(−)-L35 against S. frugiperda. This study established the chemistry basis and mechanistic foundations for the future development of pesticide candidates against fall armyworms.

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“…Under the threat of pests, the physiological and biochemical elements of the host plants will change, and the insect pests will interact (Eliezer et al,2020;Gao et al, 2020). Low toxicity pesticides and appropriate hormone derivatives can inhibit and interrupt the growth cycle of pests (Jiang et al, 2020).…”

Section: Academicpresmentioning

confidence: 99%

Establish real-time monitoring models of cotton aphid quantity based on different leaf positions in cotton seedlings

Jiao

et al. 2021

Not Bot Horti Agrobo

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Cotton aphids, Aphis gossypii glover, are major pest threats to cotton plants, leading to quality and yield loss of cotton. Rapid and accurate evaluation on the occurrence and quantity of cotton aphids can help precision management and treatment of cotton aphids. The occurrence rules of cotton aphids on different leaf positions in cotton seedling stage for two cultivars of cotton were studied. The quantity of cotton aphids in the whole cotton seedlings were predicted based on the single leaf cotton aphid quantity. The correlation analysis results showed that cotton aphids of single leaf were significantly and positively correlated with the infected time, the all leaves of the whole plant, the whole plant contained all leaves and branches. The variance analysis results showed that cotton aphids of single leaf were significant difference with the extension of infected time. Based on different leaf positions, monitoring models were constructed respectively. The modelling set’s determination coefficient of ‘Xinluzao-45’ was greater than 0.8, while ‘Lumainyan-24’ was greater than 0.6. The best monitoring leaf position was the third for ‘Xinluzao-45’, the sixth for ‘Lumianyan-24’. From the data analysis, we can realize that it is feasible to construct a monitoring model based on the occurrence of cotton aphid in one leaf in cotton seedling, and different cotton varieties have different leaf positions. This will greatly reduce the investment of manpower and time.

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New lead discovery of insect growth regulators based on the scaffold hopping strategy

Cited by 13 publications

References 23 publications

Design, Synthesis, and Insecticidal Activity of Novel Isoxazoline Compounds That Contain Meta-diamides against Fall Armyworm (Spodoptera frugiperda)

Design, Synthesis, and Insecticidal Activity of Novel Isoxazoline Compounds That Contain Meta-diamides against Fall Armyworm (Spodoptera frugiperda)

Discovery of Novel Isoxazoline Derivatives Containing Diaryl Ether against Fall Armyworms

Establish real-time monitoring models of cotton aphid quantity based on different leaf positions in cotton seedlings

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