BACKGROUND: Tropane alkaloids are known to play a role in plant defence. By blocking acetylcholine receptors, they exert insecticidal and deterrent effects against herbivore insects. Carbamates are an important class of chemical insecticides that also inhibit acetyl cholinesterase. The objective of this work was to synthesise a series of tropane alkaloids bearing a carbamate group, and to evaluate their effects against the pest Ascia monuste. The effects of the most active compounds were evaluated on the A. monuste predator Solenopsis saevissima and on the pollinator Tetragonisca angustula. RESULTS: The synthesis of carbamate-tropane alkaloids was accomplished in 4-5 steps from commercially available ketones. Results from bioassays showed that compounds 6a, 10a and 14a presented higher activities against second-instar larvae of A. monuste, with LD50 values of 1.01, 3.76 and 1.92 µg substance mg-1 insect, and TL50 values of 7.0, 15.0 and 5.0 h respectively. These compounds were also tested for their selectivity in favour of S. saevissima and T. angustula. Compound 6a, which showed the highest activity against A. monuste, also showed lower toxicity against S. saevissima. CONCLUSION: Tropane alkaloid derivatives bearing a carbamate group show potential for the development of novel insecticides against A. monuste.
BACKGROUND:Tropane alkaloids are known to play a role in plant defence. By blocking acetylcholine receptors, they exert insecticidal and deterrent effects against herbivore insects. Carbamates are an important class of chemical insecticides that also inhibit acetyl cholinesterase. The objective of this work was to synthesise a series of tropane alkaloids bearing a carbamate group, and to evaluate their effects against the pest Ascia monuste. The effects of the most active compounds were evaluated on the A. monuste predator Solenopsis saevissima and on the pollinator Tetragonisca angustula. RESULTS: The synthesis of carbamate-tropane alkaloids was accomplished in 4-5 steps from commercially available ketones. Results from bioassays showed that compounds 6a, 10a and 14a presented higher activities against second-instar larvae of A. monuste, with LD50 values of 1.01, 3.76 and 1.92 µg substance mg-1 insect, and TL50 values of 7.0, 15.0 and 5.0 h respectively. These compounds were also tested for their selectivity in favour of S. saevissima and T. angustula. Compound 6a, which showed the highest activity against A. monuste, also showed lower toxicity against S. saevissima. CONCLUSION:Tropane alkaloid derivatives bearing a carbamate group show potential for the development of novel insecticides against A. monuste.