Electrochemical C–H Sulfonylation of Hydrazones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3440 - 3444

Published: May 4, 2023

We have developed an electrochemical method for the direct C-H sulfonylation of aldehyde hydrazones using sodium sufinates as sulfonylating agent under supporting electrolyte-free conditions. This straightforward strategy afforded a library (E)-sufonylated with high tolerance various functional groups. The radical pathway this reaction has been revealed by mechanistic studies.

Language: Английский

---

Synthesis and Antifungal Activity of Coumarin Derivatives Containing Hydrazone Moiety

Chemistry & Biodiversity, Journal Year: 2024, Volume and Issue: 21(6)

Published: April 9, 2024

Plant disease control mainly relies on pesticides. In this study, a series of coumarin derivatives containing hydrazone moiety were designed and synthesized. The synthesized compounds characterized used to evaluate the antifungal activity against four pathogens, Botrytis cinerea, Alternaria solani, Fusarium oxysporum, alternata. results showed that inhibition rate some at 100 μg/mL in 96 hours reached around 70 % A. alternata, higher than positive control. corresponding EC

Language: Английский

---

Novel Pyrazole-4-Carboxamide Derivatives Containing Oxime Ether Group as Potential SDHIs to Control Rhizoctonia solani

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

---

Design, Synthesis, and Herbicidal Activity of Pyrazole Amide Derivatives as Potential Transketolase Inhibitors

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(7), P. 3334 - 3341

Published: Feb. 12, 2024

The design and synthesis of new herbicidal active compounds based on a target are great significance for the development herbicides. Transketolase (TK) plays key role in Calvin cycle plant photosynthesis has been confirmed as potential candidate to develop discover To obtain with ultraefficient targeting TK, series pyrazole amide derivatives were designed synthesized through structural optimization lead compound 4u TK target. bioassay results showed that 6ba 6bj displayed highly inhibitory effect root inhibition about 90% against Digitaria sanguinalis (DS) 80% Amaranthus retroflexus (AR) Setaria viridis (SV) by small cup method, which was better than positive control mesotrione nicosulfuron. Furthermore, exhibited an excellent (against DS) over SV) at dosage 150 g ingredient/ha foliar spray method. enzyme activity test consistent activities. Also, molecular docking analysis went deep into cavity bound strong interaction, might act TK. Above all, promising herbicide Hence, they could be developed more efficient herbicides further optimization.

Language: Английский

---

Environmental Evaluation on Toxicity, Toxic Mechanism, and Hydrolysis Behavior of Potential Acethydrazide Fungicide Candidates

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(11), P. 5636 - 5644

Published: March 8, 2024

The evaluation of toxicity and environmental behavior bioactive lead molecules is helpful in providing theoretical support for the development agrochemicals, line with sustainable ecological environment. In previous work, some acethydrazide structures have been demonstrated to exhibit excellent broad-spectrum fungicidal activity; however, its compatibility needs be further elucidated if it identified as a potential fungicide. this project, compounds F51, F58, F72, F75 zebrafish was determined at 10 μg mL–1 1 mL–1. Subsequently, toxic mechanism compound F58 preliminarily explored by histologic section TEM observations, which revealed that gallbladder volume common carp treated increased, accompanied deepened bile color, damaged plasma membrane, atrophied mitochondria cells. Approximately, F58-treated hepatocytes exhibited cytoplasmic heterogeneity, partial cellular vacuolation mitochondrial membrane rupture. Metabolomics analysis indicated differential metabolites were enriched formation-associated steroid biosynthesis, primary acid taurine hypotaurine metabolism pathways, well function-related glycerophospholipid metabolism, linolenic α-linolenic arachidonic suggesting may acute liver carp. Finally, hydrolysis dynamics investigated, obtained half-life 5.82 days. above results provide important guiding significance new green fungicides.

Language: Английский

---

Novel Pyrido[4,3-d]pyrimidine Derivatives as Potential Sterol 14α-Demethylase Inhibitors: Design, Synthesis, Inhibitory Activity, and Molecular Modeling

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(21), P. 12260 - 12269

Published: May 17, 2024

Thirty-four new pyrido[4,3-

Language: Английский

---

Fungicidal Activity of New Pyrrolo[2,3-d]thiazoles and Their Potential Action on the Tryptophan Metabolic Pathway and Wax Biosynthesis

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(21), P. 11990 - 12002

Published: May 17, 2024

The main challenge in the development of agrochemicals is lack new leads and/or targets. It critical to discover molecular targets and their corresponding ligands.

Language: Английский

---

Preparation, Antifungal Activity Evaluation, and Mechanistic Studies of Unique and Structurally Novel Pyrazole-Heterocyclic-Amide Analogues

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

Published: Jan. 21, 2025

Thirty-six novel pyrazole-heterocyclic-amide analogues were designed, synthesized, and characterized. The bioassay results showed that most target compounds exhibited good fungicidal activities against Rhizoctonia solani, Gibberella zeae, Pseudoperonospora cubensis, Helminthosporium maydis, Coniothyrium diplodiella at 20 μg/mL. Compounds 6d, 6f, 6l, 6j possessed better than the commercial fungicide prochloraz H. maydis. Their half maximal effective concentration (EC50) values 0.47, 0.26, 0.58, 0.69 μg/mL, respectively, EC50 value of was 0.77 Furthermore, inhibitory for bioactive determined sterol 14α-demethylase (CYP51), displayed they had prominent activities, also CYP51, their (IC50) 0.543, 0.29, 0.77, 0.66, 0.86 respectively. molecular dynamics simulations compound 6f stronger affinity to CYP51 prochloraz, estimated ΔGbind -44.9 -37.2 kcal/mol found

Language: Английский

---

Investigation of the Antifungal Activity and Preliminary Mode of Action of Novel 2-(1H-Indol-2-yl)-1,3,4-oxadiazole Derivatives against Botrytis cinerea

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

Published: Feb. 27, 2025

The discovery of novel leads and new targets is an important approach to address the issue fungicide resistance by development. indole skeleton has been widely utilized in agrochemicals due its unique biological activity. YZK-C22 a potent pyruvate kinase inhibitor with high antifungal Several were developed based on YZK-C22. Inspired these, [1,2,4]triazino[4,5-a]indol-1(2H)-one derivatives designed using hopping strategy; however, these compounds exhibited moderate fungicidal Unexpectedly, 2-(1H-indol-2-yl)-1,3,4-oxadiazole formed under controlled reaction conditions showed significantly higher Compounds 6c, 6d, 6f, 6j excellent activity vitro, EC50 values ranging from 0.120 0.310 μg/mL against Botrytis cinerea, more than commercial pyrimethanil (EC50 = 0.990 μg/mL). In field trials at 540 720 g active ingredient (ai)/hm2, compound 6c 81.46 86.58% efficacy B. that rate ai/hm2 (70.46%). affinity constants 6d cinerea lower Higher but implies may work as prodrugs or have different mode action. Thus, are worth being further investigated.

Language: Английский

---

Fungicidal Activity of Carboxamides Containing Spiropiperidinyl-α-methylene-γ-butyrolactones Targeting Oxysterol Binding Protein

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

Published: April 1, 2025

Oxysterol binding protein (OSBP) is a new target for oomycide development. To find more fungicidal active compounds targeting OSBP, series of carboxamides containing spiropiperidinyl-α-methylene-γ-butyrolactone and heterocyclic carboxylic acids were rationally designed synthesized by using computer-aided pesticide design method. The in vitro bioassay found that compound 5o showed broad-spectrum activity with EC50 values falling between 0.50 20.85 μg/mL against Phytophthora capsici Fusarium verticillioides, respectively, which was potent than 7c natural lead xanthatin. Compound also 44% vivo efficacy Pseudoperonospora cubensis, even at concentration 0.5 μg/mL. Fluorescence quenching microscale thermophoresis determination suggested bound to Osh4p stronger interactions oxathiapiprolin. RNA sequencing analysis discovered the ergosterol (ERG) gene cluster ribosome biogenesis eukaryotes downregulated. as good candidate OSBP deserving further studies.

Language: Английский

---