Synthesis, electrochemistry, and molluscicidal activity of nitroaromatic compounds: effects of substituents and the role of redox potential.
Abstract-Molluscicidal bioassays and electrochemical studies (measurement of first wave reduction potential, Epcl) were performed on several synthetic nitroaromatics, in relation to possible correlation between biological activity, redox potential and structural effects. Five of them presented a significant molluscicidal activity on Biomphalaria glabrata (LD50 < 20 ppm). The Epc1 values ranged from -0.532 to -0.857 V versus Ag/AgCl (0.1 M) (-0.260 to -0.585 V versus NHE), all of them, in the favorable range for reduction in vivo. Data comparison between Epc1 and molluscicidal activity indicates that the presence of the electroactive nitro group is important for the biological activity. Correlation with redox potential, however, was not evident. Structural effects seem to be the most important parameter. Higher activity is noticeable for phenols, including the para-nitro azo or hydrazo-containing compounds. No activity was observed for compounds having the benzylic substituent in meta position to the nitro group. These results suggest that activity undoubtedly involves more than reduction characteristics and that the possible formation of electrophilic species, after nitro reduction, can play an important role in molluscicidal activity against B. glabrata.
de Abreu
F C
FC
Departamento de Química, Universidade Federal de Alagoas, Maceió, Brazil.
de Paula
F S
FS
doa Santos
A F
AF
Sant'Ana
A E
AE
de Almeida
M V
MV
Cesar
E T
ET
Trindade
M N
MN
Goulart
M O
MO
D000818:Animals; D000977:Antiparasitic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004563:Electrochemistry; D020128:Inhibitory Concentration 50; D008974:Mollusca / Q000187:drug effects*; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D009578:Nitrobenzenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D012555:Schistosomiasis mansoni / Q000188:drug therapy; D012908:Snails / Q000187:drug effects; D013329:Structure-Activity Relationship
D000977:Antiparasitic Agents; D009574:Nitro Compounds; D009578:Nitrobenzenes