Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one
Autor(a) principal: | |
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Data de Publicação: | 2003 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | LOCUS Repositório Institucional da UFV |
Texto Completo: | http://dx.doi.org/10.1002/ps.717 http://www.locus.ufv.br/handle/123456789/14588 |
Resumo: | Several new compounds with potential herbicidal activity were synthesized from 2α,4α-dimethyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3-one (4). Seven aromatic alcohols were prepared by reaction of (4) with aryllithium reagents, where the aryl groups were 4-ethoxyphenyl (5, 70% yield), 4-ethylphenyl (6, 82% yield), 4-butylphenyl (7, 78% yield), 4-tert-butylphenyl (8, 81% yield), 2,4-dimethoxyphenyl (9, 75% yield), 2-ethylphenyl (10, 12% yield) and para-(4-bromophenoxy)phenyl (11, 24% yield). Reaction of the acetonide (4) with Grignard reagents formed also four aliphatic alcohols where the alkyl groups are ethyl (13, 78%), butyl (14, 85%), hexyl (15, 81%) and octyl (25, 92%). The alcohols (5), (6), (7), (8), (13), (14), (15) and (25) were reacted with thionyl chloride in pyridine, forming their respective alkenes (17, 76%), (18, 74%), (19, 83%), (20, 73%), (22, 78%), (26, 62%), (23, 77%) and (24, 66%). The effect of these compounds, at the concentration of 5.5 µg g−1, on the development of radicle and aerial parts of Sorghum bicolor (L) Moench, Euphorbia heterophylla L, Brachiaria decumbens and Desmodium tortuosum DC was evaluated. |
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Barbosa, Luiz C de AAlvarenga, Elson S deDemuner, Antônio JFigueiredo, RemilsonSilva, Antônio A da2017-12-07T13:36:42Z2017-12-07T13:36:42Z2003-06-111526-4998http://dx.doi.org/10.1002/ps.717http://www.locus.ufv.br/handle/123456789/14588Several new compounds with potential herbicidal activity were synthesized from 2α,4α-dimethyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3-one (4). Seven aromatic alcohols were prepared by reaction of (4) with aryllithium reagents, where the aryl groups were 4-ethoxyphenyl (5, 70% yield), 4-ethylphenyl (6, 82% yield), 4-butylphenyl (7, 78% yield), 4-tert-butylphenyl (8, 81% yield), 2,4-dimethoxyphenyl (9, 75% yield), 2-ethylphenyl (10, 12% yield) and para-(4-bromophenoxy)phenyl (11, 24% yield). Reaction of the acetonide (4) with Grignard reagents formed also four aliphatic alcohols where the alkyl groups are ethyl (13, 78%), butyl (14, 85%), hexyl (15, 81%) and octyl (25, 92%). The alcohols (5), (6), (7), (8), (13), (14), (15) and (25) were reacted with thionyl chloride in pyridine, forming their respective alkenes (17, 76%), (18, 74%), (19, 83%), (20, 73%), (22, 78%), (26, 62%), (23, 77%) and (24, 66%). The effect of these compounds, at the concentration of 5.5 µg g−1, on the development of radicle and aerial parts of Sorghum bicolor (L) Moench, Euphorbia heterophylla L, Brachiaria decumbens and Desmodium tortuosum DC was evaluated.engPest Management Science59(9), p. 1043–1051, Sep. 2003[3 + 4] cycloadditionHerbicidesWeedsOxabicycloSynthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-oneinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALBarbosa_et_al-2003-Pest_Management_Science.pdfBarbosa_et_al-2003-Pest_Management_Science.pdftexto completoapplication/pdf149202https://locus.ufv.br//bitstream/123456789/14588/1/Barbosa_et_al-2003-Pest_Management_Science.pdf69b8e84748e4e5f4a1d9714d48e0f2b2MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/14588/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52THUMBNAILBarbosa_et_al-2003-Pest_Management_Science.pdf.jpgBarbosa_et_al-2003-Pest_Management_Science.pdf.jpgIM Thumbnailimage/jpeg5232https://locus.ufv.br//bitstream/123456789/14588/3/Barbosa_et_al-2003-Pest_Management_Science.pdf.jpg331561a36d15fb3fb0d1286e9aa5f14cMD53123456789/145882017-12-07 22:01:08.908oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452017-12-08T01:01:08LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false |
dc.title.en.fl_str_mv |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
title |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
spellingShingle |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one Barbosa, Luiz C de A [3 + 4] cycloaddition Herbicides Weeds Oxabicyclo |
title_short |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
title_full |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
title_fullStr |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
title_full_unstemmed |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
title_sort |
Synthesis of new aliphatic and aromatic phytotoxic derivatives of 2α, 4α-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one |
author |
Barbosa, Luiz C de A |
author_facet |
Barbosa, Luiz C de A Alvarenga, Elson S de Demuner, Antônio J Figueiredo, Remilson Silva, Antônio A da |
author_role |
author |
author2 |
Alvarenga, Elson S de Demuner, Antônio J Figueiredo, Remilson Silva, Antônio A da |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Barbosa, Luiz C de A Alvarenga, Elson S de Demuner, Antônio J Figueiredo, Remilson Silva, Antônio A da |
dc.subject.pt-BR.fl_str_mv |
[3 + 4] cycloaddition Herbicides Weeds Oxabicyclo |
topic |
[3 + 4] cycloaddition Herbicides Weeds Oxabicyclo |
description |
Several new compounds with potential herbicidal activity were synthesized from 2α,4α-dimethyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3-one (4). Seven aromatic alcohols were prepared by reaction of (4) with aryllithium reagents, where the aryl groups were 4-ethoxyphenyl (5, 70% yield), 4-ethylphenyl (6, 82% yield), 4-butylphenyl (7, 78% yield), 4-tert-butylphenyl (8, 81% yield), 2,4-dimethoxyphenyl (9, 75% yield), 2-ethylphenyl (10, 12% yield) and para-(4-bromophenoxy)phenyl (11, 24% yield). Reaction of the acetonide (4) with Grignard reagents formed also four aliphatic alcohols where the alkyl groups are ethyl (13, 78%), butyl (14, 85%), hexyl (15, 81%) and octyl (25, 92%). The alcohols (5), (6), (7), (8), (13), (14), (15) and (25) were reacted with thionyl chloride in pyridine, forming their respective alkenes (17, 76%), (18, 74%), (19, 83%), (20, 73%), (22, 78%), (26, 62%), (23, 77%) and (24, 66%). The effect of these compounds, at the concentration of 5.5 µg g−1, on the development of radicle and aerial parts of Sorghum bicolor (L) Moench, Euphorbia heterophylla L, Brachiaria decumbens and Desmodium tortuosum DC was evaluated. |
publishDate |
2003 |
dc.date.issued.fl_str_mv |
2003-06-11 |
dc.date.accessioned.fl_str_mv |
2017-12-07T13:36:42Z |
dc.date.available.fl_str_mv |
2017-12-07T13:36:42Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1002/ps.717 http://www.locus.ufv.br/handle/123456789/14588 |
dc.identifier.issn.none.fl_str_mv |
1526-4998 |
identifier_str_mv |
1526-4998 |
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http://dx.doi.org/10.1002/ps.717 http://www.locus.ufv.br/handle/123456789/14588 |
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eng |
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eng |
dc.relation.ispartofseries.pt-BR.fl_str_mv |
59(9), p. 1043–1051, Sep. 2003 |
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openAccess |
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Pest Management Science |
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Pest Management Science |
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