Naslov
Synthesis, theoretical studies, and effect on the photosynthetic electron transport of trifluoromethyl arylamides

Autori
Teixeira, Róbson Ricardo ; Barros, Marcus Vinícius de Andrade ; Bressan, Gustavo Costa ; Siqueira, Raoni Pais ; dos Santos, Fabíola Suelen ; Bertazzini, Michele ; Kiralj, Rudolf ; Ferreira, Márcia Miguel Castro ; Forlani, Giuseppe

Izvornik
Pest management science (1526-498X) 73 (2017), 11; 2360-2371

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
trifluoromethyl aryl amides ; herbicides ; photosynthetic electron transport ; quantitative structure–activity relationship

Sažetak
Starting with 1-fluoro-2-nitro-4-(trifluoromethyl) benzene, the preparation of the amides was achieved via a three-step sequence, namely nucleophilic aromatic substitution, reduction with SnCl2 /HCl, and acylation reactions. The measurement of ferricyanide reduction by functionally intact spinach chloroplasts showed that several derivatives are capable of inhibiting the photosynthetic apparatus. The most active amides presented IC50 values close to 1 μmol L-1 , and showed the presence of a 4-bromophenyl group as a common structural feature. The addition of these brominated amides to the culture medium of a model cyanobacterial strain, Synechococcus elongatus PCC 6301, caused various degrees of growth inhibition. Theoretical studies (molecular modeling and quantitative structure-activity relationship) of all amides and their comparison with some known herbicides confirmed these experimental findings and provided more in-depth information about the possible molecular target of these compounds.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA