Design, synthesis, and antifungal activity of carboxamide derivatives possessing 1,2,3-triazole as potential succinate dehydrogenase inhibitors.
Pestic Biochem Physiol
; 156: 160-169, 2019 May.
Article
em En
| MEDLINE
| ID: mdl-31027576
ABSTRACT
Succinate dehydrogenase (SDH) is demonstrably one of the most important molecular targets in development of new fungicide. In our continuous efforts to discover novel SDH inhibitors, forty-two carboxamide derivatives containing 1,2,3-triazole ring were designed and synthesized, which were precisely characterized by 1H NMR, ESI-MS, elemental analysis and X-ray single-crystal diffraction. The compounds were screened for antifungal activities against phytopathogenic fungi by mycelia growth inhibition assay in vitro. Compound A3-3 exhibited significant antifungal activity against Sclerotinia sclerotiorum, Botrytis cinerea, Rhizoctonia cerealis and Gaeumannomyces graminsis with EC50 values of 1.08, 8.75, 1.67 and 5.30⯵g/mL, respectively, comparable to those of commercial SDHI boscalid. In vivo testing demonstrated that A3-3 was effective for suppressing rape sclerotinia rot, cucumber grey mould and wheat powdery mildew caused by S. sclerotiorumï¼ B. cinerea and Blumeria graminis at a dosage of 200⯵g/mL. Inhibition activities against SDH test proved the designed analogues were effective in the enzyme level. The molecular docking simulation revealed that A3-3 interacted with ARG43ï¼TYR58 and TRP173 of the SDH through hydrogen bond and pi-pi interaction, which could explain the probable mechanism of action between the inhibitor and target protein.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Succinato Desidrogenase
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Triazóis
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Inibidores Enzimáticos
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Antifúngicos
Idioma:
En
Revista:
Pestic Biochem Physiol
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
China