Synthesis of a series of validoxylamine A esters and their biological activities.
Pest Manag Sci
; 77(11): 5109-5119, 2021 Nov.
Article
de En
| MEDLINE
| ID: mdl-34240541
ABSTRACT
BACKGROUND:
The worldwide reduction in food production due to pests and diseases is still an important challenge facing today. Validoxylamine A (VAA) is a natural polyhydroxyl compound derived from validamycin, acting as an efficient trehalase inhibitor with insecticidal and antifungal activities. To extend the application and discover green pesticide, a series of ester derivatives were prepared based on VAA as a lead compound. Their biological activities were investigated against three typically agricultural disease, Rhizoctonia solani, Sclerotinia sclerotiorum and Aphis craccivora.RESULTS:
This study involved 30 novel validoxylamine A fatty acid esters (VAFAEs) synthesized by Novozym 435 and they were characterized with high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and proton nuclear magnetic resonance (1 H-NMR). Of these 30 derivatives, most compounds showed improved antifungal activity, and 12 novel compounds showed improved insecticidal activity. When reacted with pentadecanoic acid, compound 14 showed the highest inhibitory activity against R. solani [median effective concentration (EC50 ) 0.01 µmol L-1 ], while the EC50 value of VAA was 34.99 µmol L-1 . Furthermore, 21 novel VAFAEs showed higher inhibitory activity against S. sclerotiorum. Validoxylamine A oleic acid ester, compound 21, exhibited the highest insecticidal activity against A. craccivora [median lethal concentration (LC50 ) 39.63 µmol L-1 ], while the LC50 value of Pymetrozine was 50.45 µmol L-1 , a commercialized pesticide against A. craccivora.CONCLUSION:
Combining our results, esterification of VAA by introducing different acyl donors was beneficial for the development of new eco-friendly drugs in the field of pesticides.Mots clés
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Esters
Langue:
En
Journal:
Pest Manag Sci
Sujet du journal:
TOXICOLOGIA
Année:
2021
Type de document:
Article
Pays d'affiliation:
Chine