Antifeedant effect of polygodial and drimenol derivatives against Spodoptera frugiperda and Epilachna paenulata and quantitative structure‐activity analysis

• Published in: Pest management science Vol. 74; no. 7; pp. 1623 - 1629
• Main Authors: Montenegro, Iván J, del Corral, Soledad, Diaz Napal, Georgina N, Carpinella, María C, Mellado, Marco, Madrid, Alejandro M, Villena, Joan, Palacios, Sara M, Cuellar, Mauricio A
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01-07-2018; Wiley Subscription Services, Inc
• Subjects: Agronomy; Carbonyl groups; Carbonyls; Derivatives; Epilachana paenulata; Epilachna; Insects; nordrimane; Organic chemistry; Pests; Polygodial; Sesquiterpenoids; Spodoptera frugiperda; Structure-activity relationships; Spodoptera frugiperda; polygodial; Epilachana paenulata; nordrimane
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.4853

BACKGROUND
The antifeedant activity of 18 sesquiterpenoids of the drimane family (polygodial, drimenol and derivatives) was investigated.
RESULTS
Polygodial, drimanic and nordrimanic derivatives were found to exert antifeedant effects against two insect species, Spodoptera frugiperda and Epilachna paenulata, which are pests of agronomic interest, indicating that they have potential as biopesticide agents. Among the 18 compounds tested, the epoxynordrimane compound (11) and isonordrimenone (4) showed the highest activity [50% effective concentration (EC50) = 23.28 and 25.63 nmol cm−2, respectively, against S. frugiperda, and 50.50 and 59.00 nmol/cm2, respectively, against E. paenulata].
CONCLUSION
The results suggest that drimanic compounds have potential as new agents against S. frugiperda and E. paenulata. A quantitative structure–activity relationship (QSAR) analysis of the whole series, supported by electronic studies, suggested that drimanic compounds have structural features necessary for increasing antifeedant activity, namely a C‐9 carbonyl group and an epoxide at C‐8 and C‐9. © 2018 Society of Chemical Industry
In this work, drimanic compounds showed effective antifeedant activity against the biological targets Spodoptera frugiperda and Epilachna paenulata. The most active compounds were epoxy nordrimane and isonordrimenone. The findings for these molecules open up new possibilities for the control of these species, which affect large areas of cultivation.