Novel Insecticidal Benzo[4,5]imidazo[1,2‐b]pyrazole Derivatives Identified through Ring‐Closure Scaffold Hopping on Fipronil DOI Open Access
Cong Zhou, Guanglong Li, Sihui Wang

et al.

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract A series of innovative benzo[4,5]imidazo[1,2‐ b ]pyrazole scaffold containing compounds were rationally designed through a ring‐closure hopping strategy and synthetized with an intermediate derivatization approach. Physicochemical properties analysis indicated the potential pesticide‐likeness target compounds. The optimal compound A14 showed relatively good insecticidal activity against P. xylostella , LC 50 value 37.58 mg/L, demonstrated lower acute fish toxicity compared to fipronil. Docking binding mode that bound GABAR H‐bond between amide group residue 6’Thr. differences in modes fipronil may be key factor for reduced activities. elucidated SAR profile lay foundation further structural optimization derivatives.

Language: Английский

Discovery of new N-Phenylamide Isoxazoline derivatives with high insecticidal activity and reduced honeybee toxicity DOI

Yong‐Chao Gao,

Xiangmin Song,

Tianhao Jia

et al.

Pesticide Biochemistry and Physiology, Journal Year: 2024, Volume and Issue: 200, P. 105843 - 105843

Published: March 1, 2024

Language: Английский

Citations

8
Rational Design of Insecticidal Isoxazolines Containing Sulfonamide or Sulfinamide Structure as Antagonists of GABA Receptors with Reduced Toxicities to Honeybee and Zebrafish DOI

Shuai Yang,

Jiahong Tang,

Benjie Li

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(39), P. 14211 - 14220

Published: Sept. 22, 2023

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

Language: Английский

Citations

16
Prediction of Potential Risk for Ten Azole and Benzimidazole Fungicides with the Aryl Hydrocarbon Receptor Agonistic Activity to Aquatic Ecosystems DOI
Chao Shen, Xiaoyan Ding, Wenhua Rao

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 73(2), P. 1167 - 1181

Published: Dec. 31, 2024

Azole and benzimidazole fungicides are widely used agrochemicals to prevent treat fungal growth frequently detected in aquatic environments. Here, we aimed assess the ecological risks of ten currently azole fungicides, which with aryl hydrocarbon receptor (AhR) agonistic activity, their transformation products (TPs). We obtained over 400 types aerobic TPs for fungicides. Some (approximately 26.7%) exhibited potential AhR activity toxicity different species. Meanwhile, some compounds chlorine element benzene ring structure environmental persistence mobile ability. Several them were environments, posing ecosystems. These harmful should be given attention. This study provides important insight into caused by can provide theoretical guidance pollution control.

Language: Английский

Citations

2
Structural optimization based on 4,5-dihydropyrazolo[1,5-a]quinazoline scaffold for improved insecticidal activities DOI

Shuai Yang,

Benjie Li,

Jiahong Tang

et al.

Pesticide Biochemistry and Physiology, Journal Year: 2023, Volume and Issue: 195, P. 105533 - 105533

Published: July 16, 2023

Language: Английский

Citations

6
Discovery of novel thiazolyl anthranilic diamide derivatives as insecticidal candidates DOI Open Access

Shuai Yang,

Jiahong Tang,

Hongxiang Peng

et al.

Pest Management Science, Journal Year: 2023, Volume and Issue: 79(12), P. 5260 - 5269

Published: Aug. 21, 2023

Agricultural pests have caused huge losses in agricultural production and threaten global food security. Synthetic insecticides remain the major control method. However, with rapid development of pest resistance increasingly stringent regulations on pesticide usage, efficient novel structures is particularly urgent.Twenty-six anthranilic diamide derivatives containing thiazole moiety were designed based scaffold hopping strategy. Bioassay results indicated that compound 6e exhibited excellent insecticidal activity against a susceptible strain diamondback moth (Plutella xylostella) median lethal concentration (LC50 ) 0.65 mg L-1 , which was similar to chlorantraniliprole = 0.53 ). Compound showed marginally lower 50.45 than 31.98 chlorantraniliprole-resistant P. xylostella larvae, suggesting cross-resistance (resistance ratios, 77.6-fold 60.3-fold, respectively). also good fall armyworm beet mortalities 74% 64%, respectively, at 5 concentration. In addition, compounds 12a delayed toxicity red imported fire ant mortality rates 84% 85% (respectively) after days treatment 1.0 superior chlorantraniliprole.The introduction into scaffolds resulted leads activities potential application controlling ants. The work guides discovery molecules thiazole-containing scaffold. © 2023 Society Chemical Industry.

Language: Английский

Citations

5
Novel Insecticidal Benzo[4,5]imidazo[1,2‐b]pyrazole Derivatives Identified through Ring‐Closure Scaffold Hopping on Fipronil DOI Open Access
Cong Zhou, Guanglong Li, Sihui Wang

et al.

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 27, 2024

Abstract A series of innovative benzo[4,5]imidazo[1,2‐ b ]pyrazole scaffold containing compounds were rationally designed through a ring‐closure hopping strategy and synthetized with an intermediate derivatization approach. Physicochemical properties analysis indicated the potential pesticide‐likeness target compounds. The optimal compound A14 showed relatively good insecticidal activity against P. xylostella , LC 50 value 37.58 mg/L, demonstrated lower acute fish toxicity compared to fipronil. Docking binding mode that bound GABAR H‐bond between amide group residue 6’Thr. differences in modes fipronil may be key factor for reduced activities. elucidated SAR profile lay foundation further structural optimization derivatives.

Language: Английский

Citations

0