Brasil | Artigo

Síntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico

dc.creatorBarbosa, Luiz Cláudio de Almeida
dc.creatorDemuner, Antônio Jacinto
dc.creatorMaltha, Célia Regina Álvares
dc.creatorSilva, Patrícia Silvana da
dc.creatorSilva, Antônio Alberto da
dc.date2019-05-03T11:56:50Z
dc.date2019-05-03T11:56:50Z
dc.date2003-09
dc.date.accessioned2023-09-27T20:53:25Z
dc.date.available2023-09-27T20:53:25Z
dc.identifier1678-7064
dc.identifierhttp://dx.doi.org/10.1590/S0100-40422003000500006
dc.identifierhttp://www.locus.ufv.br/handle/123456789/24965
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8950237
dc.descriptionSeveral compounds related to helminthosporic acid (3) were synthesized via the [3+4] cycloaddition. The reaction of 3-hydroxymethyl-2-methylfuran (12) with 1,1,3,3-tetrabromo-4-methylpentan-2-one (13) resulted in 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (8) (37%) and 7-hydroxymethyl-2a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (14) (12%), which were converted into 7-formyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (16) (32% from 8) and 7-formyl-2a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (18) (40% from 14), respectively. Reduction of (8) resulted in 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6 -en-3a-ol (11) (63% from 8) and 7-hydroxymethyl-4a-isopropyl-1a-methyl-8-oxabicyclo[3.2.1]oct-6-en-3 b-ol (15) (30% from 8). The 4a-isopropyl-1a-methyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-en-7-oic acid (19) was obtained by oxidation of (16) (78%). The results of biological tests are described in details. The best result was observed for compound (15) that caused 76% inhibition on the root growth of D. tortuosum.
dc.formatpdf
dc.formatapplication/pdf
dc.languagepor
dc.publisherQuímica Nova
dc.relationv. 26, n. 5, p. 655- 660, set.- out. 2003
dc.rightsOpen Access
dc.subject[ 3+ 4] cycloaddition
dc.subjectHelminthosporic acid
dc.subjectHerbicides
dc.titleSíntese e avaliação da atividade fitotóxica de novos análogos oxigenados do ácido helmintospórico
dc.typeArtigo


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