Design, Synthesis, and Structure–Activity Relationship of Economical Triazole Sulfonamide Aryl Derivatives with High Fungicidal Activity DOI
Jian Lin, Si Zhou, Junxing Xu

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2020, Volume and Issue: 68(25), P. 6792 - 6801

Published: May 22, 2020

Plant fungal diseases have caused great decreases in crop quality and yield. As one of the considerable agricultural diseases, cucumber downy mildew (CDM) by pseudoperonospora cubensis seriously influences production cucumber. Amisulbrom is a commercial fungicide developed Nissan Chemical, Ltd., for control oomycetes that highly effective against CDM. However, synthesis amisulbrom has high cost because introduction bromoindole ring. In addition, continuous use might increase risk resistance development. Hence, there an imperative to develop active fungicides with new scaffolds but low this study, series 1,2,4-triazole-1,3-disulfonamide derivatives were designed, synthesized, screened. Compound 1j showed comparable fungicidal activity amisulbrom, it was ecofriendly. It potential be as candidate Further investigations structure–activity relationship exhibited structural requirements appropriate modification N-alkyl benzylamine groups activity. This research will provide powerful guidance design lead compounds novel skeleton cost.

Language: Английский

Design, synthesis, and biological activity of novel spiro‐pyrazolo[1,5‐a]quinazolines derivatives as potential insecticides DOI
Guangkai Yao, Mengfan Wang,

Benjie Li

et al.

Pest Management Science, Journal Year: 2022, Volume and Issue: 79(3), P. 1164 - 1174

Published: Nov. 13, 2022

Arylpyrazole insecticides display broad-spectrum insecticidal activity against insect pests. However, the high toxicity toward honeybees associated with fipronil prohibits its agronomic utility. To explore reducing of aryl pyrazole analogs to bees, a series new spiro-pyrazolo[1,5-a]quinazoline derivatives were designed and synthesized.Bioassay results showed that these compounds exhibited good activity. In particular, compound 5f Plutella xylostella larvae (median lethal contentration, LC50 = 1.43 mg L-1 ) was equivalent fipronil. Moreover, some also Solenopsis invicta. Importantly, bee study confirmed had much lower acute oral toxicity, median dose (LD50 1.15 μg bee-1 three four orders magnitude greater than (0.0012 ). Electrophysiological studies conducted using honeybee γ-aminobutyric acid receptor heterologously expressed in Xenopus oocytes explain reduced 5f. The inhibitory effect (16.29 μmol determined be approximately 700-fold (0.023 ).These could potential candidates lead structures for discovery novel low toxicity. © 2022 Society Chemical Industry.

Language: Английский

Citations

24
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

13
AquaticTox: A Web-Based Tool for Aquatic Toxicity Evaluation Based on Ensemble Learning to Facilitate the Screening of Green Chemicals DOI Creative Commons
Xing-Xing Shi, Zhi-Zheng Wang, Yuliang Wang

et al.

Environment & Health, Journal Year: 2024, Volume and Issue: 2(4), P. 202 - 211

Published: April 1, 2024

The widespread use of chemical products inevitably brings many side effects as environmental pollutants. Toxicological assessment compounds to aquatic life plays an important role in protecting the environment from their hazards. However, vivo animal testing approaches for toxicity evaluation are time-consuming, expensive, and ethically limited, especially when there a great number compounds. In silico modeling methods can effectively improve efficiency save costs. Here, we present web-based server, AquaticTox, which incorporates series ensemble models predict acute organic organisms, covering Oncorhynchus mykiss, Pimephales promelas, Daphnia magna, Pseudokirchneriella subcapitata, Tetrahymena pyriformis. predictive built through learning algorithms based on six base learners. These outperform all corresponding single models, achieving area under curve (AUC) scores 0.75–0.92. Compared best average precisions have been increased by 12–22%. Additionally, self-built knowledge structure-aquatic toxic mode action (MOA) relationship was integrated into AquaticTox mechanism analysis. Hopefully, user-friendly tool (https://chemyang.ccnu.edu.cn/ccb/server/AquaticTox); could facilitate identification chemicals design green molecules.

Language: Английский

Citations

5
A Potential Multitarget Insect Growth Regulator Candidate: Design, Synthesis, and Biological Activity of Novel Acetamido Derivatives Containing Hexacyclic Pyrazole Carboxamides DOI

Bingbo Guo,

Lei Chen,

Shihui Luo

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(18), P. 10271 - 10281

Published: April 24, 2024

Insect growth regulators (IGRs) are important green insecticides that disrupt normal and development in insects to reduce the harm caused by pests crops. The ecdysone receptor (EcR) three chitinases

Language: Английский

Citations

5
Design, Synthesis, and Structure–Activity Relationship of Economical Triazole Sulfonamide Aryl Derivatives with High Fungicidal Activity DOI
Jian Lin, Si Zhou, Junxing Xu

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2020, Volume and Issue: 68(25), P. 6792 - 6801

Published: May 22, 2020

Plant fungal diseases have caused great decreases in crop quality and yield. As one of the considerable agricultural diseases, cucumber downy mildew (CDM) by pseudoperonospora cubensis seriously influences production cucumber. Amisulbrom is a commercial fungicide developed Nissan Chemical, Ltd., for control oomycetes that highly effective against CDM. However, synthesis amisulbrom has high cost because introduction bromoindole ring. In addition, continuous use might increase risk resistance development. Hence, there an imperative to develop active fungicides with new scaffolds but low this study, series 1,2,4-triazole-1,3-disulfonamide derivatives were designed, synthesized, screened. Compound 1j showed comparable fungicidal activity amisulbrom, it was ecofriendly. It potential be as candidate Further investigations structure–activity relationship exhibited structural requirements appropriate modification N-alkyl benzylamine groups activity. This research will provide powerful guidance design lead compounds novel skeleton cost.

Language: Английский

Citations

36