Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae)
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional da UFSCAR |
Texto Completo: | https://repositorio.ufscar.br/handle/ufscar/11328 |
Resumo: | The pheromones play an important role in chemical communication between alive organisms. They can be used in agriculture to pest control. The brown-caterpillar, Thyrinteina arnobia, is considered in Brazil a major pest of Eucalyptus species. The damage is caused by tree defoliation due to the attack of caterpillars. In this work the asymmetric synthesis of four stereoisomers of 3,4-epoxy-6,9-eneicosadiene, sex pheromone component of T. arnobia, was accomplished in 11 steps with an overall yield of 16 to 20%. The key step of the synthetic route involved the Sharpless asymmetric epoxidation of Z- and E-2-penten-1-ol which delivered the corresponding epoxyalcohols in 70-76% yield and 80-90% ee. Electroantennographic analysis (EAG) as well as behavioural studies in laboratory and field will be conducted to evaluate the action of these compounds in insects and possible application in monitoring and pest control. |
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Paiva, Marcelo Montanha deCorrêa, Arlene Gonçalveshttp://lattes.cnpq.br/7425467156776144http://lattes.cnpq.br/57939542873138978dac6ca6-5977-47c5-ab72-0896b02e46d02019-04-29T17:13:06Z2019-04-29T17:13:06Z2013-01-31PAIVA, Marcelo Montanha de. Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae). 2013. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2013. Disponível em: https://repositorio.ufscar.br/handle/ufscar/11328.https://repositorio.ufscar.br/handle/ufscar/11328The pheromones play an important role in chemical communication between alive organisms. They can be used in agriculture to pest control. The brown-caterpillar, Thyrinteina arnobia, is considered in Brazil a major pest of Eucalyptus species. The damage is caused by tree defoliation due to the attack of caterpillars. In this work the asymmetric synthesis of four stereoisomers of 3,4-epoxy-6,9-eneicosadiene, sex pheromone component of T. arnobia, was accomplished in 11 steps with an overall yield of 16 to 20%. The key step of the synthetic route involved the Sharpless asymmetric epoxidation of Z- and E-2-penten-1-ol which delivered the corresponding epoxyalcohols in 70-76% yield and 80-90% ee. Electroantennographic analysis (EAG) as well as behavioural studies in laboratory and field will be conducted to evaluate the action of these compounds in insects and possible application in monitoring and pest control.Os feromônios exercem papel importante na comunicação química entre organismos vivos. Eles podem ser empregados na agricultura para o controle de pragas. A lagarta parda, Thyrinteina arnobia, é considerada no Brasil uma importante praga de espécies de Eucalyptus. Os danos são causados através da desfolhação das árvores devido ao ataque de lagartas. Nesse trabalho a síntese assimétrica dos 4 estereoisômeros de 3,4-epoxi-6,9-eneicosadieno, componente do feromônio sexual de T. arnobia, foi realizada em 11 etapas com rendimento de 16-20% de rendimento global. A etapa chave da rota sintética envolveu a reação de epoxidação assimétrica de Sharpless do Z- e E-2-penten-1-ol que forneceu os epoxiálcoois correspondentes em 70-76% de rendimento e 80-90% ee. Análises eletroantenográficas (EAG) e estudos comportamentais de laboratório e de campo permitirão entender a ação destes compostos no comportamento do inseto e posterior uso no controle e monitoramento de pragas.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)CAPES: Código de Financiamento 001porUniversidade Federal de São CarlosCâmpus São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarFeromônioCG-EADThyrinteina arnobiaSínteseAssimétricaEstereoisômerosCIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICASíntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae)info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisOnline600600d0f2b9e6-a39b-4adb-8930-18725207ea16info:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINALDissertação_Marcelo Montanha de Paiva UFSCar 24_04_19.pdfDissertação_Marcelo Montanha de Paiva UFSCar 24_04_19.pdfDissertaçãoapplication/pdf3631315https://repositorio.ufscar.br/bitstream/ufscar/11328/1/Disserta%c3%a7%c3%a3o_Marcelo%20Montanha%20de%20Paiva%20UFSCar%2024_04_19.pdf7c8dcc2c32254b11fe665b3ed79616b5MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81957https://repositorio.ufscar.br/bitstream/ufscar/11328/3/license.txtae0398b6f8b235e40ad82cba6c50031dMD53TEXTDissertação_Marcelo Montanha de Paiva UFSCar 24_04_19.pdf.txtDissertação_Marcelo Montanha de Paiva UFSCar 24_04_19.pdf.txtExtracted texttext/plain92878https://repositorio.ufscar.br/bitstream/ufscar/11328/4/Disserta%c3%a7%c3%a3o_Marcelo%20Montanha%20de%20Paiva%20UFSCar%2024_04_19.pdf.txt3fee8900a1316ff6d340a8783fe299b2MD54THUMBNAILDissertação_Marcelo Montanha de Paiva UFSCar 24_04_19.pdf.jpgDissertação_Marcelo Montanha de Paiva UFSCar 24_04_19.pdf.jpgIM Thumbnailimage/jpeg10048https://repositorio.ufscar.br/bitstream/ufscar/11328/5/Disserta%c3%a7%c3%a3o_Marcelo%20Montanha%20de%20Paiva%20UFSCar%2024_04_19.pdf.jpgc9860d38678f5c4f4f6a0c6c02dff3ebMD55ufscar/113282023-09-18 18:31:22.276oai:repositorio.ufscar.br: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Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-09-18T18:31:22Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
title |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
spellingShingle |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) Paiva, Marcelo Montanha de Feromônio CG-EAD Thyrinteina arnobia Síntese Assimétrica Estereoisômeros CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA |
title_short |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
title_full |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
title_fullStr |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
title_full_unstemmed |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
title_sort |
Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae) |
author |
Paiva, Marcelo Montanha de |
author_facet |
Paiva, Marcelo Montanha de |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/5793954287313897 |
dc.contributor.author.fl_str_mv |
Paiva, Marcelo Montanha de |
dc.contributor.advisor1.fl_str_mv |
Corrêa, Arlene Gonçalves |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7425467156776144 |
dc.contributor.authorID.fl_str_mv |
8dac6ca6-5977-47c5-ab72-0896b02e46d0 |
contributor_str_mv |
Corrêa, Arlene Gonçalves |
dc.subject.por.fl_str_mv |
Feromônio CG-EAD Thyrinteina arnobia Síntese Assimétrica Estereoisômeros |
topic |
Feromônio CG-EAD Thyrinteina arnobia Síntese Assimétrica Estereoisômeros CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA::SINTESE ORGANICA |
description |
The pheromones play an important role in chemical communication between alive organisms. They can be used in agriculture to pest control. The brown-caterpillar, Thyrinteina arnobia, is considered in Brazil a major pest of Eucalyptus species. The damage is caused by tree defoliation due to the attack of caterpillars. In this work the asymmetric synthesis of four stereoisomers of 3,4-epoxy-6,9-eneicosadiene, sex pheromone component of T. arnobia, was accomplished in 11 steps with an overall yield of 16 to 20%. The key step of the synthetic route involved the Sharpless asymmetric epoxidation of Z- and E-2-penten-1-ol which delivered the corresponding epoxyalcohols in 70-76% yield and 80-90% ee. Electroantennographic analysis (EAG) as well as behavioural studies in laboratory and field will be conducted to evaluate the action of these compounds in insects and possible application in monitoring and pest control. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-01-31 |
dc.date.accessioned.fl_str_mv |
2019-04-29T17:13:06Z |
dc.date.available.fl_str_mv |
2019-04-29T17:13:06Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
PAIVA, Marcelo Montanha de. Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae). 2013. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2013. Disponível em: https://repositorio.ufscar.br/handle/ufscar/11328. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/11328 |
identifier_str_mv |
PAIVA, Marcelo Montanha de. Síntese assimétrica dos componentes do feromônio sexual da lagarta-parda, Thyrinteina arnobia (Lepidoptera: Geometridae). 2013. Dissertação (Mestrado em Química) – Universidade Federal de São Carlos, São Carlos, 2013. Disponível em: https://repositorio.ufscar.br/handle/ufscar/11328. |
url |
https://repositorio.ufscar.br/handle/ufscar/11328 |
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openAccess |
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Universidade Federal de São Carlos Câmpus São Carlos |
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Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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Universidade Federal de São Carlos Câmpus São Carlos |
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