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Previous issue date: 2015-02-27 / 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 folowing 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. / A busca crescente por fontes de intermediários químicos que sejam renováveis e biodegradáveis faz do cardanol alquil fenol um dos constituintes mais importantes e promissores da indústria de castanha de caju e da sua cadeia produtiva. O cardanol foi extraído, destilado, hidrogenado e realizadas as sínteses dos seguintes intermediários: cloridrina de cadeia saturada (CCS) (6a), cloridrina de cadeia insaturada (CCI) (6a-d), epóxido de cadeia saturada (ECS) (7a), epóxido de cadeia insaturada (ECI) (7a-d), diol de cadeia saturada (DCS) (9a), diol de cadeia insaturada (DCI) (9a-d), derivado de 4-amino antipirina de cadeia saturada (DAACS) (10a), derivados de 4-amino antipirina de cadeia insaturada (DAACI) (10a-d), derivado de morfolina de cadeia saturada (DMCS) (11a), diol metoxilado de cadeia saturada (DMTCS) (12a), diol metoxilado de cadeia insaturada (DMTCI) (12a-d), complexo de Cu(II)-diol de cadeia saturada (Cu(II)-DCS) (13a), complexo de Cu(II)-diol cadeia insaturada (Cu(II)-DCI) (13a-d), complexo de Cu(II) com derivados de amino antipirina de cadeia saturada (Cu(II)-DAACS) (14a) e complexo de Cu(II) com derivados de 4-amino antipirina de cadeia insaturada (Cu(II)-DAACI) (14a-d). Os compostos sintetizados foram caracterizados por espectroscopia de ressonância magnética nuclear (RMN), espectroscopia vibracional do infravermelho (IV), espectroscopia eletrônica de ultravioleta-visível (UV-Vis), termogravimetria (TG) e espectroscopia de massas (EM). Os compostos DCS (9a), DCI (9a-d), DAACS (10a), DAACI (10a-d), Cu(II)-DCS (13a), Cu(II)-DCI (13a-d), Cu(II)-DAACS (14a) e Cu(II)-DAACI (14a-d) foram utilizados para realização dos bioensaios de toxicidade com larvas de Aedes aegypti de 3o e 4o estádios (Rockefeller). A análise de toxicidade mostrou atividade inseticida/larvicida promissora para os compostos DCS (9a), Cu(II)-DCS (13a) e Cu(II)-DAACS (14a) com as CL50 40,19 mg L-1 (ppm), 38,84 mg L-1 (ppm) e 59,41 mg L-1 (ppm), respectivamente por 24 horas de exposição para Aedes aegypti. Os compostos (9a), (9a-d) e (10a) também mostraram atividade promissora contra as larvas do 3o e 4o estádio de Anopheles aquasalis tendo apresentado as seguintes CL50: 9,65 mgL-1; 23,36 mgL-1 e 52,55 mgL-1 respetivamente.
| Identifer | oai:union.ndltd.org:IBICT/oai:tede.ufgd.edu.br:tede/329 |
| Date | 27 February 2015 |
| Creators | Cossa, Teresa Manuel |
| Contributors | Arruda, Eduardo José de, Beatriz, Adilson, Faoro, Eliandro, Micheletti, Ana Camila |
| Publisher | Universidade Federal da Grande Dourados, Química - Mestrado, UFGD, Brasil, FACET |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | Portuguese |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFGD, instname:Universidade Federal da Grande Dourados, instacron:UFGD |
| Rights | http://creativecommons.org/licenses/by-nc-nd/4.0/, info:eu-repo/semantics/openAccess |
| Relation | 3119929381378724512, 500, 500, 600, 8816595718120871258, 1571700325303117195 |
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