Benzoxazoles as novel herbicidal agents
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | LOCUS Repositório Institucional da UFV |
Texto Completo: | https://doi.org/10.1002/ps.5111 http://www.locus.ufv.br/handle/123456789/24400 |
Resumo: | Despite the need to develop new herbicides with different modes of action, due to weed resistance, many important classes of compounds have been studied poorly for this purpose. Benzoxazoles are considered privileged structures because of their biological activities, but their phytotoxic activities have not received a lot of attention until now.Double vinylic substitution reactions were carried out to furnish four 2‐nitromethylbenzoxazoles and one oxazolidine. Benzoxazol‐2‐ylmethanamine was obtained by reduction of compound 3a. These compounds were evaluated for their phytotoxicity in Allium cepa (onion), Solanum lycopersicum (tomato), Cucumis sativus (cucumber) and Sorghum bicolor (sorghum). Comparison with oxazolidine analogue allowed us to understand that the benzoxazolic structure is very important for the herbicidal activity. All the synthesized compounds exhibited biological activity on seed germination. The four 2‐nitromethylbenzoxazoles showed phytotoxic activity and the 5‐chloro‐2‐(nitromethyl)benzo[d]oxazole (3b) exhibited higher inhibition than the commercial herbicide against all four plant species tested. © 2018 Society of Chemical Industry. |
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Pereira-Flores, Milton E.Sangi, Diego P.Meira, Yuri G.Moreira, Natália M.Lopes, Thais A.Leite, Mathias P.Alvarenga, Elson S.2019-04-09T14:42:30Z2019-04-09T14:42:30Z2019-0115264998https://doi.org/10.1002/ps.5111http://www.locus.ufv.br/handle/123456789/24400Despite the need to develop new herbicides with different modes of action, due to weed resistance, many important classes of compounds have been studied poorly for this purpose. Benzoxazoles are considered privileged structures because of their biological activities, but their phytotoxic activities have not received a lot of attention until now.Double vinylic substitution reactions were carried out to furnish four 2‐nitromethylbenzoxazoles and one oxazolidine. Benzoxazol‐2‐ylmethanamine was obtained by reduction of compound 3a. These compounds were evaluated for their phytotoxicity in Allium cepa (onion), Solanum lycopersicum (tomato), Cucumis sativus (cucumber) and Sorghum bicolor (sorghum). Comparison with oxazolidine analogue allowed us to understand that the benzoxazolic structure is very important for the herbicidal activity. All the synthesized compounds exhibited biological activity on seed germination. The four 2‐nitromethylbenzoxazoles showed phytotoxic activity and the 5‐chloro‐2‐(nitromethyl)benzo[d]oxazole (3b) exhibited higher inhibition than the commercial herbicide against all four plant species tested. © 2018 Society of Chemical Industry.engPest Management ScienceVolume 75, Issue 01, Pages 262- 269, January 2019HerbicideBenzoxazolesSynthesisSorghumCucumberOnionTomatoBenzoxazoles as novel herbicidal agentsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfinfo:eu-repo/semantics/openAccessreponame:LOCUS Repositório Institucional da UFVinstname:Universidade Federal de Viçosa (UFV)instacron:UFVORIGINALartigo.pdfartigo.pdftexto completoapplication/pdf960112https://locus.ufv.br//bitstream/123456789/24400/1/artigo.pdfe2a9a3c32d74f23f08cd6099984388edMD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81748https://locus.ufv.br//bitstream/123456789/24400/2/license.txt8a4605be74aa9ea9d79846c1fba20a33MD52123456789/244002019-04-09 11:43:46.108oai:locus.ufv.br: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Repositório InstitucionalPUBhttps://www.locus.ufv.br/oai/requestfabiojreis@ufv.bropendoar:21452019-04-09T14:43:46LOCUS Repositório Institucional da UFV - Universidade Federal de Viçosa (UFV)false |
dc.title.en.fl_str_mv |
Benzoxazoles as novel herbicidal agents |
title |
Benzoxazoles as novel herbicidal agents |
spellingShingle |
Benzoxazoles as novel herbicidal agents Pereira-Flores, Milton E. Herbicide Benzoxazoles Synthesis Sorghum Cucumber Onion Tomato |
title_short |
Benzoxazoles as novel herbicidal agents |
title_full |
Benzoxazoles as novel herbicidal agents |
title_fullStr |
Benzoxazoles as novel herbicidal agents |
title_full_unstemmed |
Benzoxazoles as novel herbicidal agents |
title_sort |
Benzoxazoles as novel herbicidal agents |
author |
Pereira-Flores, Milton E. |
author_facet |
Pereira-Flores, Milton E. Sangi, Diego P. Meira, Yuri G. Moreira, Natália M. Lopes, Thais A. Leite, Mathias P. Alvarenga, Elson S. |
author_role |
author |
author2 |
Sangi, Diego P. Meira, Yuri G. Moreira, Natália M. Lopes, Thais A. Leite, Mathias P. Alvarenga, Elson S. |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Pereira-Flores, Milton E. Sangi, Diego P. Meira, Yuri G. Moreira, Natália M. Lopes, Thais A. Leite, Mathias P. Alvarenga, Elson S. |
dc.subject.pt-BR.fl_str_mv |
Herbicide Benzoxazoles Synthesis Sorghum Cucumber Onion Tomato |
topic |
Herbicide Benzoxazoles Synthesis Sorghum Cucumber Onion Tomato |
description |
Despite the need to develop new herbicides with different modes of action, due to weed resistance, many important classes of compounds have been studied poorly for this purpose. Benzoxazoles are considered privileged structures because of their biological activities, but their phytotoxic activities have not received a lot of attention until now.Double vinylic substitution reactions were carried out to furnish four 2‐nitromethylbenzoxazoles and one oxazolidine. Benzoxazol‐2‐ylmethanamine was obtained by reduction of compound 3a. These compounds were evaluated for their phytotoxicity in Allium cepa (onion), Solanum lycopersicum (tomato), Cucumis sativus (cucumber) and Sorghum bicolor (sorghum). Comparison with oxazolidine analogue allowed us to understand that the benzoxazolic structure is very important for the herbicidal activity. All the synthesized compounds exhibited biological activity on seed germination. The four 2‐nitromethylbenzoxazoles showed phytotoxic activity and the 5‐chloro‐2‐(nitromethyl)benzo[d]oxazole (3b) exhibited higher inhibition than the commercial herbicide against all four plant species tested. © 2018 Society of Chemical Industry. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-04-09T14:42:30Z |
dc.date.available.fl_str_mv |
2019-04-09T14:42:30Z |
dc.date.issued.fl_str_mv |
2019-01 |
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 |
https://doi.org/10.1002/ps.5111 http://www.locus.ufv.br/handle/123456789/24400 |
dc.identifier.issn.none.fl_str_mv |
15264998 |
identifier_str_mv |
15264998 |
url |
https://doi.org/10.1002/ps.5111 http://www.locus.ufv.br/handle/123456789/24400 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartofseries.pt-BR.fl_str_mv |
Volume 75, Issue 01, Pages 262- 269, January 2019 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Pest Management Science |
publisher.none.fl_str_mv |
Pest Management Science |
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