Design, synthesis, and insecticidal evaluation of novel anthranilic diamides of <scp><i>N</i>‐pyridylpyrazole</scp> derivatives containing <scp>3‐thioethers</scp>

Sun, Pengwei; Zhang, Ze; Li, Linshan; Wang, Xinyao; Xiong, Lixia; Yang, Na; Li, Yuxin; Li, Zhengming

doi:10.1002/jhet.4422

Cited by 4 publications

(2 citation statements)

References 56 publications

(58 reference statements)

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“…67 Furthermore, Sun Peng-wei and co-workers found compound 64 exhibited good insecticidal activities against M. separata at 5 mg/L. 68 Bioassay results indicated that some of the compounds synthesized by Hua Xue-wen and co-workers incorporated a N-cyanomethylsulfilimine on the pyrazole (compound 65), 69 possessed certain degrees of insecticidal activities against M. separata.…”

Section: Part Bmentioning

confidence: 99%

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

2023

J. Agric. Food Chem.

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

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Section: Part Bmentioning

confidence: 99%

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

2023

J. Agric. Food Chem.

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“…Thienopyrimidine, with anti-inflammatory and antimicrobial properties, has widespread applications in the fields of tumour inhibition, anti-tuberculosis, the treatment of acute myocardial infarction and pet repellent [42][43][44]. However, beyond these established applications, our research has unveiled an untapped potential of this compound, its fluorescence.…”

Section: Introductionmentioning

confidence: 99%

Thienopyrimidine‐derived multifunctional fluorescence sensor for the detection of Cu²⁺, Fe³⁺, and PPi in different solvents

Shi,

Kang,

Liu

et al. 2024

Luminescence

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Hydrazine substituted thienopyrimidine, a new fluorophore, was used to synthesize a novel Schiff base R1 as a chemosensor via the condensation with p‐formyltriphenylamine, and the structure was confirmed using nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) analysis. When treated with Cu2+ in dimethylsulfoxide (DMSO)/H2O buffer, R1 showed a phenomenon of fluorescence quenching, which was reversible with the action of ethylenediaminetetraacetic acid (EDTA). When treated with Fe3+ in dimethylformamide (DMF)/H2O buffer, R1 exhibited the same phenomenon, but fluorescence was recovered with inorganic pyrophosphate (PPi) quantitatively. The complexation ratios for R1‐Cu2+ and R1‐Fe3+ were both 1:2, which were manifested by MS titrations and corresponding Job's plots. The limits of detection of R1 for Cu2+ and Fe3+ were 3.11 × 10−8 and 1.24 × 10−7 M, respectively. The sensing mechanism of R1 toward Cu2+ and Fe3+ was confirmed using density functional theory calculations and electrostatic potential analysis. Test strips of R1 were fabricated successfully for on‐site detection of Cu2+ and Fe3+. In addition, R1 was applied to recognize Cu2+ and Fe3+ in actual water samples with satisfactory recovery.

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Design, synthesis, antifungal activity, and molecular docking of novel trifluoromethyl pyrimidine derivatives containing 1,3,4‐oxadiazole and thioether moieties as potential succinate dehydrogenase inhibitors

Pan,

Wu,

Yan

et al. 2023

Journal of Heterocyclic Chem

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Succinate dehydrogenase (SDH), a pivotal enzyme linking the respiratory electron transport chain and tricarboxylic acid (TCA) cycle, has been identified as an ideal target for developing effective fungicides. In this study, 20 novel trifluoromethyl pyrimidine derivatives containing 1,3,4‐oxadiazole and thioether moieties were prepared and characterized their structures by 1H NMR, 13C NMR, and HRMS. Bioassay results showed that some of the target compounds revealed moderate to good in vitro antifungal activities toward Rhizoctonia solani (R. solani), Botryosphaeria dothidea (B. dothidea), Phomopsis sp., Botrytis cinerea (B. cinerea), Fusarium oxysporum (F. oxysporum), Sclerotinia sclerotiorum (S. sclerotiorum), Phytophthora infestans (P. infestans), and Magnaporthe oryzae (M. oryzae). In particular, compounds 6g and 6i had better in vitro antifungal activity against B. cinerea, with the EC50 values of 19.43 and 28.22 μg/mL, respectively, than that of Pyrimethanil (57.30 μg/mL). As well, compound 6r exhibited good in vitro antifungal activity against F. oxysporum, with the EC50 value of 3.61 μg/mL, which were lower than that of Boscalid (0.40 μg/mL). In addition, the molecular docking simulation revealed that compound 6r interacted with GLN‐150, ASP‐153, LYS‐151, GLY‐154, and GLY‐228 of SDH through hydrogen bond, which could explain the probable mechanism of action between the target compounds and SDH. This is the first report on the antifungal activity of novel trifluoromethyl pyrimidine derivatives containing 1,3,4‐oxadiazole and thioether moieties as potential SDH inhibitors.

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Design, synthesis, and insecticidal evaluation of novel anthranilic diamides of N‐pyridylpyrazole derivatives containing 3‐thioethers

Cited by 4 publications

References 56 publications

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

Thienopyrimidine‐derived multifunctional fluorescence sensor for the detection of Cu²⁺, Fe³⁺, and PPi in different solvents

Design, synthesis, antifungal activity, and molecular docking of novel trifluoromethyl pyrimidine derivatives containing 1,3,4‐oxadiazole and thioether moieties as potential succinate dehydrogenase inhibitors

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Design, synthesis, and insecticidal evaluation of novel anthranilic diamides of N‐pyridylpyrazole derivatives containing 3‐thioethers

Cited by 4 publications

References 56 publications

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators

Thienopyrimidine‐derived multifunctional fluorescence sensor for the detection of Cu2+, Fe3+, and PPi in different solvents

Design, synthesis, antifungal activity, and molecular docking of novel trifluoromethyl pyrimidine derivatives containing 1,3,4‐oxadiazole and thioether moieties as potential succinate dehydrogenase inhibitors

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Thienopyrimidine‐derived multifunctional fluorescence sensor for the detection of Cu²⁺, Fe³⁺, and PPi in different solvents