Discovery of quinazoline compound as a novel nematicidal scaffold

Wang, Yu; Song, Hongyi; Wang, Sheng; Cai, Qingfeng; Zhang, Yong; Zou, Yue; Liu, Xing; Chen, Jixiang

doi:10.1016/j.pestbp.2022.105310

Cited by 14 publications

(13 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As previously mentioned, a saponification process was used to create the intermediate compound 4 . , Compound 3 (15.4 mmol) was mixed with 4 mol/L NaOH (46.2 mmol) solution and then stirred at 80 °C for reaction. After reaction for 2 h, the reaction solution was added into ice water (60 mL) and adjusted to pH 4–5 with HCl.…”

Section: Methodsmentioning

confidence: 99%

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

Jiang

Feng

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

Spodoptera frugiperda is a major migratory agricultural pest, which seriously impedes agricultural production around the world. To discover potent compounds against S. frugiperda, a number of novel isoxazoline derivatives were designed and synthesized and created on account of the identified lead compound F32 (4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methyl-N-(3-propionamidophenyl)benzamide). Based on the three-dimensional quantitative structure–activity relationship of those compounds, the compound G22 (N-(4-acetamidophenyl)-4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide) was developed. A bioassay showed that G22 is highly lethal to S. frugiperda (LC50 = 1.57 mg/L), a more effective control than insecticides fipronil (LC50 = 78.8 mg/L) and chlorantraniliprole (LC50 = 1.60 mg/L). Field trials were also implemented to identify candidate agents. Furthermore, from the insect γ-aminobutyric acid (GABA) enzyme-linked immunosorbent assay, it is obvious that G22 could up-regulate the expression of GABA of insects, which showed a similar result to fipronil. The analysis of molecular docking exhibited that the hydrophobic effect and hydrogen bonds play key roles in the combination between G22 with GABA receptors. This study provides a potent isoxazoline candidate compound for the S. frugiperda control.

show abstract

Section: Methodsmentioning

confidence: 99%

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

Jiang

Feng

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…besseyi, and D. destructor were cultured according to our previously reported methods and then collected using the Bellman funnel method. As previously reported, the second instar larvae of B.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Nematicidal Activity, and Mechanism of Novel Amide Derivatives Containing an 1,2,4-Oxadiazole Moiety

Wang,

Song,

Wang

et al. 2023

J. Agric. Food Chem.

Self Cite

View full text Add to dashboard Cite

To discover new nematicides, a series of novel amide derivatives containing 1,2,4-oxadiazole were designed and synthesized. Several compounds showed excellent nematicidal activity. The LC 50 values of compounds A7, A18, and A20−A22 against pine wood nematode (Bursaphelenchus xylophilus), rice stem nematode (Aphelenchoides besseyi), and sweet potato stem nematode (Ditylenchus destructor) were 1.39−3.09 mg/L, which were significantly better than the control nematicide tioxazafen (106, 49.0, and 75.0 mg/L, respectively). Compound A7 had an outstanding inhibitory effect on nematode feeding, reproductive ability, and egg hatching. Compound A7 effectively promoted the oxidative stress of nematodes and caused intestinal damage to nematodes. Compound A7 significantly inhibited the activity of succinate dehydrogenase (SDH) in nematodes, leading to blockage of electron transfer in the respiratory chain and thereby hindering the synthesis of adenosine triphosphate (ATP), which consequently affects the entire oxidative phosphorylation process to finally cause nematode death. Therefore, compound A7 can be used as a potential SDH inhibitor in nematicide applications.

show abstract

“…Plant nematodes, as one of the important plant pathogens, engage in economic losses due to plant nematodes to the tune of $157 billion annually [118][119][120]. Due to the highly insidious nature of plant nematodes that are difficult to control, current management with chemical nematicides remains one of the most effective means [121][122][123][124][125][126].…”

Section: Nematicidal Activitymentioning

confidence: 99%

Research progress of oxazole derivatives in the discovery of agricultural chemicals

Wang,

Song,

Cai

et al. 2023

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

The search for new scaffolds is one of the important goals in the discovery of new pesticides, and the oxazoles as an important five‐membered heterocyclic compound are widely used in the discovery of new pesticides. Oxazoles ring are often used as the scaffolding structure or bridging chain to connect different reactive groups. In recent years, oxazoles have made rapid progress in the discovery of new pesticides, especially in the discovery of fungicides, insecticides, and acaricides. A systematic review of the recent research progress of oxazoles in the discovery of new pesticides is of interest. Therefore, we comprehensively reviewed the application of oxazole compounds in the discovery of new pesticides from 2003 to 2023; summarized the fungicidal, antibacterial, insecticidal, acaricidal, and herbicidal activities of oxazoles; and discussed the structure–activity relationship, physiochemical and mechanism of action, with the aim of providing inspiration and ideas for the discovery of oxazoles as novel agrochemicals.

show abstract

Discovery of quinazoline compound as a novel nematicidal scaffold

Cited by 14 publications

References 33 publications

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

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

Design, Synthesis, Nematicidal Activity, and Mechanism of Novel Amide Derivatives Containing an 1,2,4-Oxadiazole Moiety

Research progress of oxazole derivatives in the discovery of agricultural chemicals

Contact Info

Product

Resources

About