Síntese, caracterização e atividade biológica de ligantes e complexos de cobre (II) baseados no cardanol para o controle de mosquitos (diptera - culicidae)

Abstract

The increasing search for renewable and biodegradable chemical intermediates makes cardanol one of the most important and promissing component on cashew industry. The cardanol was extracted, distilled, hydrogenated and carried out in brief the following intermediates, hydrogenated and following intermediats were synthesized: saturated chain chlorohydrin (CCS) (6a), unsaturated chain chlorohydrin (CCI) (6a-d), unsaturated chain epoxide (ECS) (7a), unsaturated chain epoxide (ECI) (7a-d), saturated chain diol (DCS ) (9a), unsaturated chain diol (DCI) (9a-d), derived from saturated chain 4-amino antipyrine (DAACS) (10a), derived from unsaturated chain amino antipyrine DACI (10a-d), saturated chain morpholine derivative (DMCS) (11a), methoxylated diol saturated chain DMTS (12a), methoxylated unsaturated chain diol DMTCI (12a-d), the complex of Cu(II) saturated chain diol, (Cu(II)-DCS) (13a), complex of Cu(II) unsaturated chain diol (Cu(II)-DCI) (13a-d), Cu(II) complex with amino antipyrine saturated chain derivative (Cu(II)-DAACS) (14a) and Cu(II) complex with amino antipyrine unsaturated chain derivative (Cu(II)-DAACI) (14a-d). The synthesized compounds were characterized by proton nuclear magnetic resonance (NMR), infrared vibrational spectroscopy (IR), scanning electron ultraviolet-visible spectroscopy (UV-Vis), thermogravimetry (TG) and mass spectroscopy (ME). The compounds (9a) DCS, DCI (9a-d), DAACS (10a), DAACI (10a-d), Cu(II)-DCS (13a), Cu(II)-DCI (13a-d), Cu(II)-DAACS (14a) and Cu(II)-DAACI (14a-d) were subjected to bioassay toxicity with Aedes aegypti (strain Rockefeller). The bioassay analysis showed insecticidal activity/larvicide promising for compounds DS (9a), Cu(II)-DCS (13a) and Cu(II)-DAACS (14a) with the LC50 40.19 mg L-1 (ppm), 38.84 mg L-1 (ppm) and 59.41 mg L- 1 (ppm), respectively in 24 hours exposure. The compounds (9a), (9a-d) and (10a) also showed promising activity against the larvae of the 3rd and 4th stage of Anopheles aquasalis, and had the following LC50: 9.65 mg L-1; 23.36 mg L-1 and 52, 55 mg L-1 respectively.