دورية أكاديمية

Design, Synthesis, and Fungicidal Activities of Novel N -(Pyrazol-5-yl)benzamide Derivatives Containing a Diphenylamine Moiety.

التفاصيل البيبلوغرافية
العنوان: Design, Synthesis, and Fungicidal Activities of Novel N -(Pyrazol-5-yl)benzamide Derivatives Containing a Diphenylamine Moiety.
المؤلفون: Ma YD; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China., Zhou H; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China., Lin GT; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China., Wu KH; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China., Xu G; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.; State Key Laboratory of Crop Stress Biology for Arid Areas, Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, People's Republic of China., Liu X; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.; State Key Laboratory of Crop Stress Biology for Arid Areas, Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, People's Republic of China., Xu D; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.; Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Key Laboratory of Integrated Pest Management on the Loess Plateau of Ministry of Agriculture and Rural Affairs, College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100, People's Republic of China.; State Key Laboratory of Crop Stress Biology for Arid Areas, Key Laboratory of Botanical Pesticide R&D in Shaanxi Province, Yangling, Shaanxi 712100, People's Republic of China.
المصدر: Journal of agricultural and food chemistry [J Agric Food Chem] 2024 Mar 27; Vol. 72 (12), pp. 6691-6701. Date of Electronic Publication: 2024 Mar 18.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 0374755 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-5118 (Electronic) Linking ISSN: 00218561 NLM ISO Abbreviation: J Agric Food Chem Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Washington, American Chemical Society.
مواضيع طبية MeSH: Antifungal Agents*/pharmacology , Fungicides, Industrial*/chemistry , Strobilurins* , Acetates* , Amides* , Imines*, Structure-Activity Relationship ; Diphenylamine/chemistry ; Molecular Docking Simulation ; Benzamides ; Succinate Dehydrogenase
مستخلص: To accelerate the development of novel fungicides, a variety of N -(pyrazol-5-yl)benzamide derivatives with a diphenylamine moiety were designed and synthesized using a pharmacophore recombination strategy based on the structure of pyrazol-5-yl-aminophenyl-benzamides. The bioassay results demonstrated that most of the target compounds had excellent in vitro antifungal activities against Sclerotinia sclerotiorum , Valsa mali , and Botrytis cinerea . In particular, compound 5IIIh exhibited remarkable activity against S. sclerotiorum (EC 50 = 0.37 mg/L), which was similar to that of fluxapyroxad (EC 50 = 0.27 mg/L). In addition, compound 5IIIc (EC 50 = 1.32 mg/L) was observed to be more effective against V. mali than fluxapyroxad (EC 50 = 12.8 mg/L) and comparable to trifloxystrobin (EC 50 = 1.62 mg/L). Furthermore, compound 5IIIh demonstrated remarkable in vivo protective antifungal properties against S. sclerotiorum , with an inhibition rate of 96.8% at 100 mg/L, which was close to that of fluxapyroxad (99.6%). Compounds 5IIIc (66.7%) and 5IIIh (62.9%) exhibited good in vivo antifungal effects against V. mali at 100 mg/L, which were superior to that of fluxapyroxad (11.1%) but lower than that of trifloxystrobin (88.9%). The succinate dehydrogenase (SDH) enzymatic inhibition assay was conducted to confirm the mechanism of action. Molecular docking analysis further revealed that compound 5IIIh has significant hydrogen-bonding, π-π, and p-π conjugation interactions with ARG 43, SER 39, TRP 173, and TYR 58 in the binding site of SDH, and the binding mode was similar to that of the commercial fungicide fluxapyroxad. All of the results suggest that compound 5IIIh could be a potential SDH inhibitor, offering a valuable reference for future studies.
فهرسة مساهمة: Keywords: N-(pyrazol-5-yl)benzamide; diphenylamine; fungicidal activity; molecular docking; structure−activity relationships; succinate dehydrogenase inhibitor
المشرفين على المادة: 0 (Antifungal Agents)
F625Z36B2D (trifloxystrobin)
7U8P4NAR2S (fluxapyroxad)
9N3CBB0BIQ (Diphenylamine)
6X80438640 (benzamide)
0 (Fungicides, Industrial)
0 (Benzamides)
EC 1.3.99.1 (Succinate Dehydrogenase)
0 (Strobilurins)
0 (Acetates)
0 (Amides)
0 (Imines)
تواريخ الأحداث: Date Created: 20240318 Date Completed: 20240328 Latest Revision: 20240328
رمز التحديث: 20240329
DOI: 10.1021/acs.jafc.3c07567
PMID: 38498985
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-5118
DOI:10.1021/acs.jafc.3c07567