Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene

Detalhes bibliográficos
Autor(a) principal: Gomes,Anni C. S.
Data de Publicação: 2020
Outros Autores: Demuner,Antonio J., Alvarenga,Elson S., Gondim,João P. E., Fonseca,Andressa R., Buonicontro,Dalila S., Pilau,Eduardo J., Silva,Evandro
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000901805
Resumo: Nematode is a major problem in agriculture, the effective way to control this pest is through chemical control, but the efficient molecules present in the market have great toxicity to mammals and birds. Thus, there is a constant demand for the development of new nematicide molecules. This study describes the synthesis of 21 novel esters derived from norbornadiene and evaluation of their potential activity against Meloidogyne javanica. The esters 5-25 presented 50% mortality of the nematodes. The acid 3 and the ester 4 caused 96 and 93% mortality of the nematodes, respectively. The lethal concentration to kill 50% of the nematodes (LD50) were determined as being 11.8 µg mL-1 for the acid 3 and 99.4 µg mL-1 for the ester 4. According to the results obtained it is believed that polarity seems to be a key factor for the higher activity of compound 3 compared to structurally similar ester derivatives.
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spelling Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from NorbornadieneMeloidogyne javanicaDiels-Alderbicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acidbut-2-ynedioic acidNematode is a major problem in agriculture, the effective way to control this pest is through chemical control, but the efficient molecules present in the market have great toxicity to mammals and birds. Thus, there is a constant demand for the development of new nematicide molecules. This study describes the synthesis of 21 novel esters derived from norbornadiene and evaluation of their potential activity against Meloidogyne javanica. The esters 5-25 presented 50% mortality of the nematodes. The acid 3 and the ester 4 caused 96 and 93% mortality of the nematodes, respectively. The lethal concentration to kill 50% of the nematodes (LD50) were determined as being 11.8 µg mL-1 for the acid 3 and 99.4 µg mL-1 for the ester 4. According to the results obtained it is believed that polarity seems to be a key factor for the higher activity of compound 3 compared to structurally similar ester derivatives.Sociedade Brasileira de Química2020-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000901805Journal of the Brazilian Chemical Society v.31 n.9 2020reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20200067info:eu-repo/semantics/openAccessGomes,Anni C. S.Demuner,Antonio J.Alvarenga,Elson S.Gondim,João P. E.Fonseca,Andressa R.Buonicontro,Dalila S.Pilau,Eduardo J.Silva,Evandroeng2020-08-17T00:00:00Zoai:scielo:S0103-50532020000901805Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2020-08-17T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
title Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
spellingShingle Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
Gomes,Anni C. S.
Meloidogyne javanica
Diels-Alder
bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid
but-2-ynedioic acid
title_short Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
title_full Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
title_fullStr Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
title_full_unstemmed Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
title_sort Synthesis and Evaluation of Nematicidal Activity of Compounds Derived from Norbornadiene
author Gomes,Anni C. S.
author_facet Gomes,Anni C. S.
Demuner,Antonio J.
Alvarenga,Elson S.
Gondim,João P. E.
Fonseca,Andressa R.
Buonicontro,Dalila S.
Pilau,Eduardo J.
Silva,Evandro
author_role author
author2 Demuner,Antonio J.
Alvarenga,Elson S.
Gondim,João P. E.
Fonseca,Andressa R.
Buonicontro,Dalila S.
Pilau,Eduardo J.
Silva,Evandro
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Gomes,Anni C. S.
Demuner,Antonio J.
Alvarenga,Elson S.
Gondim,João P. E.
Fonseca,Andressa R.
Buonicontro,Dalila S.
Pilau,Eduardo J.
Silva,Evandro
dc.subject.por.fl_str_mv Meloidogyne javanica
Diels-Alder
bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid
but-2-ynedioic acid
topic Meloidogyne javanica
Diels-Alder
bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid
but-2-ynedioic acid
description Nematode is a major problem in agriculture, the effective way to control this pest is through chemical control, but the efficient molecules present in the market have great toxicity to mammals and birds. Thus, there is a constant demand for the development of new nematicide molecules. This study describes the synthesis of 21 novel esters derived from norbornadiene and evaluation of their potential activity against Meloidogyne javanica. The esters 5-25 presented 50% mortality of the nematodes. The acid 3 and the ester 4 caused 96 and 93% mortality of the nematodes, respectively. The lethal concentration to kill 50% of the nematodes (LD50) were determined as being 11.8 µg mL-1 for the acid 3 and 99.4 µg mL-1 for the ester 4. According to the results obtained it is believed that polarity seems to be a key factor for the higher activity of compound 3 compared to structurally similar ester derivatives.
publishDate 2020
dc.date.none.fl_str_mv 2020-09-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000901805
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000901805
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20200067
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.31 n.9 2020
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
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