Synthesis, Biological Activity, and Toxicity to Zebrafish Embryo of Benzamides Substituted with 1,2,4-Oxadiazole-Linked Pyrazole DOI
Yingying Wang, Changyuan Wu, Zhiyun Li

et al.

ACS Agricultural Science & Technology, Journal Year: 2023, Volume and Issue: 3(10), P. 911 - 917

Published: Oct. 4, 2023

To explore novel pesticidal lead compounds with potential activity, a series of new benzamide substituted 1,2,4-oxadiazole-linked pyrazole were designed and synthesized based on the active substructure splice principle. The preliminary bioassay revealed that most exhibited good larvicidal activities against Mythimna separate, Helicoverpa armigera, Ostrinia nubilalis, Spodoptera frugiperda. Additionally, all displayed potent antifungal Pyricularia oryzae, 13h was compound an inhibitory rate 88.9% at concentration 50 mg/L. acute toxicity assay found toxic to zebrafish embryos LC50 value 2.43 Thus, strong insecticidal properties 13h, together its moderate toxicity, make it promising candidate for pesticide lead.

Language: Английский

Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study DOI

Guantian Yang,

Cong Zhou, Yutong Wang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(6), P. 2827 - 2841

Published: Feb. 3, 2023

In order to develop anthranilic diamides with novel chemotypes, a series of acrylamide linkers were designed and synthesized. The results preliminary bioassays indicated that compounds monofluoroalkene amide linker (Z-isomer) exhibited good larvicidal activity against lepidopteran pests. LC50 values compound A23 Mythimna separata Plutella xylostella 1.44 3.48 mg·L-1, respectively, while those chlorantraniliprole 0.08 0.06 respectively. Compound also the same level lethal potency resistant susceptible strains Spodoptera frugiperda at 50 mg·L-1. similar symptoms as in test larvae. Comparative molecular field analysis was conducted demonstrate structure-activity relationship. Central neuron calcium imaging experiments potential ryanodine receptor (RyR) activators activated channels both endoplasmic reticulum cell membrane. Molecular docking suggested had better binding P. RyR than chlorantraniliprole. MM|GBSA dG bind value 117.611 kcal·mol-1. Monofluoroalkene introduced into diamide insecticides for first time brought chemotype insect activators. feasibility fluoroalkenes insecticide fragments explored.

Language: Английский

Citations

14
Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani DOI
Bo Luo,

Yuerui Wu,

Xinran Ren

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(17), P. 9599 - 9610

Published: April 22, 2024

In the search for novel succinate dehydrogenase inhibitor (SDHI) fungicides to control Rhizoctonia solani, thirty-five pyrazole-4-carboxamides bearing either an oxime ether or ester group were designed and prepared based on strategy of molecular hybridization, their antifungal activities against five plant pathogenic fungi also investigated. The results indicated that majority compounds containing demonstrated outstanding in vitro activity R. some displayed pronounced Sclerotinia sclerotiorum Botrytis cinerea. Particularly, compound 5e exhibited most promising solani with EC50 value 0.039 μg/mL, which was about 20-fold better than boscalid (EC50 = 0.799 μg/mL) 4-fold more potent fluxapyroxad 0.131 μg/mL). Moreover, detached leaf assay showed could suppress growth rice leaves significant protective efficacies (86.8%) at 100 superior (68.1%) (80.6%), indicating application prospects. addition, (SDH) enzymatic inhibition revealed generated remarkable SDH (IC50 2.04 μM), obviously those 7.92 μM) 6.15 μM). Furthermore, SEM analysis caused a disruption characteristic structure morphology hyphae, resulting damage. docking fit into identical binding pocket through hydrogen bond interactions as well fluxapyroxad, they had similar mechanism. density functional theory electrostatic potential calculations provided useful information regarding electron distribution transfer, contributed understanding structural features mechanism lead compound. These findings suggested be candidate SDHI warranting further investigation.

Language: Английский

Citations

5
Design, Synthesis, and Biological Activities of Novel Phenylpyrazole Derivatives Containing a Trifluoromethylselenyl Moiety DOI

Lefeng Dong,

Wenning Chang,

Wu‐Lin Yang

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(30), P. 11396 - 11403

Published: July 20, 2023

Phenylpyrazole insecticides are widely used for crop protection and public sanitation by blocking gamma-aminobutyric acid (GABA)-gated chloride channels glutamate-gated (GluCl) channels. Herein, 36 novel phenylpyrazole derivatives containing a trifluoromethylselenyl moiety were designed synthesized based on the strategy of introducing selenium element. All derivative structures characterized nuclear magnetic resonance (NMR) high-resolution mass spectrometry (HRMS). The insecticidal activity results indicated that some had good activities against Aedes albopictus (A. albopictus) Plutella xylostella (P. xylostella). larvicidal mosquitos compounds 5, 5a, 5k, 5l at 0.5 mg/L was 60–80%. At concentration 500 mg/L, 5h, 5l, 5r, 6, 6j, 6k, 7 showed 70–100% mortality P. xylostella. Among them, 5 6 better effect with rates 87 93% 50 respectively. It summarized different binding poses fipronil in Musca domestica (M. domestica) GABARs might lead to disparity bioactivity from docking studies. Toxicity tests zebrafish suggested compound may be slightly less toxic embryos than hatching rate.

Language: Английский

Citations

12
Design, Synthesis, and Herbicidal Activity of Novel 5-Acylbarbituric Acid Derivatives Containing Maleimide Moieties and Evaluation of Their Mode of Action DOI

Shibo Han,

Shumin Wang,

Shuyue Fu

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

In continuation of our search for herbicide lead compounds with novel structures and enhanced activities, a total thirty 5-acylbarbituric acid derivatives containing maleimide moieties were designed synthesized, their herbicidal activities evaluated in the greenhouse. The bioassay results showed that some newly synthesized target had good activity, which BT-IV-1 displayed an excellent inhibitory effect on Brassia campestris, Amaranthus retroflexus, blitum, Chenopodium album, Portulaca oleracea, Abutilon theophrasti, inhibition rate > 80% at dosage 37.5 g ha-1, it was determined to be safe Oryza sativa, Zea mays, Panicum miliaceum 75 ha-1. Studying molecular mechanism by phenotypic observation, membrane permeability evaluation, docking, vitro maize protoporphyrinogen oxidase (PPO) activity evaluation reveals is PPO inhibitor. present work indicates can serve as potential compound further development PPO-inhibiting herbicides.

Language: Английский

Citations

0
Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators DOI
Shaoqing Du, Xueping Hu

Journal of Agricultural and Food Chemistry, Journal Year: 2023, Volume and Issue: 71(8), P. 3620 - 3638

Published: Feb. 15, 2023

The world's hunger is continuously rising due to conflicts, climate change, pandemics (such as the recent COVID-19), and crop pests diseases. It widely accepted that zero impossible without using agrochemicals control Diamide insecticides are one of used green developed in years play important roles controlling lepidopteran pests. Currently, eight diamine have been commercialized, which target insect ryanodine receptors. This review summarizes development optimization processes diamide derivatives acting receptor activators. also discusses pest resistance possible solutions overcome limitations posed by resistance. Thus, with reference structural biology, this study provides an impetus for designing developing improved insecticidal activities.

Language: Английский

Citations

9
Phthalimides: developments in synthesis and functionalization DOI Creative Commons
Fatemeh Doraghi,

Mohammad Hossein Morshedsolouk,

Nawrooz Ali Zahedi

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(32), P. 22809 - 22827

Published: Jan. 1, 2024

Phthalimides are prevalent in pharmaceuticals, and natural products, etc . The synthesis of phthalimides catalyzed by transition metals under metal-free conditions as well functionalization NH-phthalimides described this review.

Language: Английский

Citations

3
Screening of Oxygenated Aromatic Compounds for Potential Antifungal Activity against Geotrichum citri-aurantii through Structure–Activity Relationship Analysis DOI

Jinxin Che,

Fei Pan, Xiumei Chen

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2022, Volume and Issue: 70(42), P. 13787 - 13795

Published: Oct. 14, 2022

Sour rot caused by Geotrichum citri-aurantii (G. citri-aurantii) is responsible for huge economic losses during citrus fruit storage. However, the availability of chemical fungicides controlling this disease rather limited. In present study, antifungal activities 25 oxygenated aromatic compounds against mycelial growth G. were determined, and their corresponding structure-activity relationships illustrated. Salicylaldehyde (pMIC = 2.689) possessed strongest inhibitory effect on growth, followed thymol 2.478) o-phthalaldehyde 2.429). Molecular electrostatic potential molecular orbital analysis showed that efficiency test was determined number location hydroxyl aldehyde groups length ester chain. All selected quantitative structure-antifungal activity relationship (QSAR) analysis. A three-dimensional-QSAR model inhibitors established demonstrated good predictive capability [comparative field analysis, q2 0.532, optimum components (ONC) =10, R2 0.996, F 560.325, standard error estimation (SEE) 0.034, two descriptors; comparative similarity index 0.675, ONC 6, 0.989, 263.354, SEE 0.054, five descriptors]. QSAR substitution at position 1 with hydrophilic electron-withdrawing produced a hydrogen donor thus improved activity. contrast, positions 4 or 5 electron-donating decreased its These findings can provide theoretical guidance preparing effective drugs sour in citrus.

Language: Английский

Citations

9
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
Design, Synthesis, and Insecticidal Activities of Novel N‐Pyridylpyrazole Amide Derivatives Containing a Maleimide DOI Open Access
Lu Zhang,

Yijin Kong,

Xusheng Shao

et al.

Chemistry & Biodiversity, Journal Year: 2023, Volume and Issue: 20(6)

Published: April 10, 2023

To discover 'me-better' insecticidal active molecules targeting ryanodine receptors (RyRs), a series of novel N-pyridylpyrazole amide derivatives containing maleimide were designed and synthesized in accordance with the prior investigations our group. Preliminary bioassay findings indicated some compounds exhibited good larvicidal activities against lepidopteran pests at concentration 500 mg L-1 . Compound 9 j showed 60 % M. Separata 50 b 40 P. xylostella Molecular docking study that H-bonds, π-π interaction cation-π made for binding b, Xylostella RyR. These results could be developed as promising leads.

Language: Английский

Citations

4
Novel pyrazole-4-carboxamides and aromatic carboxamides derivatives containing a hydrazine moiety as potential SDHIs DOI
Bo Luo, Wei Zhou,

X.L. Zhang

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1292, P. 136202 - 136202

Published: July 13, 2023

Language: Английский

Citations

4