title: Preparation of achiral and chiral (E)-enaminopyran-2,4-diones and their phytotoxic activity.
abstract: A short and efficient approach to a range of new chiral and achiral functionalized (E)-enaminopyran-2,4-diones starting with commercially available dehydroacetic acid is described. The phytotoxic properties of these (E)-enaminopyran-2,4-diones were evaluated by their ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings. A different sensitivity of the two crops was evident with the (E)-enaminopyran-2,4-diones. The most active compounds were also tested against two weeds, Ipomoea grandifolia and Brachiaria decumbens. To the best of our knowledge, this is the first report describing enaminopyran-2,4-diones as potential plant growth regulators.
authors.affiliation: Institute of Chemistry, University of Campinas, UNICAMP, P.O. Box 6154, 13084-971, Campinas, SP, Brazil.
authors.forename: Luiz C
authors.initials: LC
authors.lastname: Dias
authors.forename: Antônio J
authors.initials: AJ
authors.lastname: Demuner
authors.forename: Vânia M M
authors.initials: VM
authors.lastname: Valente
authors.forename: Luiz C A
authors.initials: LC
authors.lastname: Barbosa
authors.forename: Felipe T
authors.initials: FT
authors.lastname: Martins
authors.forename: Antônio C
authors.initials: AC
authors.lastname: Doriguetto
authors.forename: Javier
authors.initials: J
authors.lastname: Ellena
mesh_terms: D035201:Brachiaria / Q000187:drug effects; D018553:Cucumis sativus / Q000187:drug effects / Q000254:growth & development; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology*; D027741:Ipomoea / Q000187:drug effects; D010937:Plant Growth Regulators / Q000138:chemical synthesis* / Q000494:pharmacology; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D036226:Seedlings / Q000187:drug effects / Q000254:growth & development; D045868:Sorghum / Q000187:drug effects / Q000254:growth & development; D013329:Structure-Activity Relationship
chemical_list: C539999:3-(1-(sec-butylamino)ethylidene)-6-methyl-3H-pyran-2,4-dione; D006540:Herbicides; D010937:Plant Growth Regulators; D011714:Pyrans; D011753:Pyrones; C027493:dehydroacetic acid