Author | Mendes, Lorena Lessa | |
Author | Varejão, Jodieh Oliveira Santana | |
Author | Sousa, Jose Antonio de | |
Author | Carneiro, José Walkimar de Mesquita | |
Author | Valdo, Ana K. | |
Author | Martins, Felipe Terra | |
Author | Robert Weingart, Barreto | |
Author | Silva, Toshik Iarley da | |
Author | Kohlhoff, Markus | |
Author | Pilau, Eduardo Jorge | |
Author | Varejão, Eduardo Vinícius Vieira | |
Access date | 2024-02-27T19:20:31Z | |
Available date | 2024-02-27T19:20:31Z | |
Document date | 2022 | |
Citation | MENDES, Lorena Lessa et al. herbicide application. 2,5-Diketopiperazines via Intramolecular N-Alkylation of Ugi Adducts: A Contribution to the Synthesis, Density Functional Theory Study, X-ray Characterization, and Potential Herbicide Application J. Agric. Food Chem, v. 70, n. 6, p. 1799–1809, 2022. doi.org/10.1021/acs.jafc.1c07790 | en_US |
ISSN | 0021-8561 | en_US |
URI | https://www.arca.fiocruz.br/handle/icict/62822 | |
Language | eng | en_US |
Publisher | ACS Publications | en_US |
Related document | https://www.arca.fiocruz.br/handle/icict/56009 | en_US |
Rights | restricted access | en_US |
Title | 2,5-Diketopiperazines via intramolecular n-alkylation of ugi adducts: a contribution to the synthesis, density functional theory study, x-ray characterization, and potential herbicide application | en_US |
Type | Article | en_US |
Abstract | To investigate the herbicidal potential of 2,5-diketopiperazines (2,5-DKPs), we applied a known protocol to produce a series of 2,5-DKPs through intramolecular N-alkylation of Ugi adducts. However, the method was not successful for the cyclization of adducts presenting aromatic rings with some substituents at the ortho position. Results from DFT calculations showed that the presence of voluminous groups at the ortho position of a benzene ring results in destabilization of the transition structure. Lower activation enthalpies for the SN2-type cyclization of Ugi adducts were obtained when bromine, instead of a chlorine anion, is the leaving group, indicating that the activation enthalpy for the cyclization step controls the formation of the 2,5-DKP. Some Ugi adducts and 2,5-DKPs formed crystals with suitable qualities for single-crystal X-ray diffraction data collection. Phytotoxic damage of some 2,5-DKPs on leaves of the weed Euphorbia heterophylla did not differ from those caused by the commercial herbicide diquat. | en_US |
Affilliation | Universidade Federal de Viçosa. Departamento de Quimica. Viçosa, MG, Brazil | en_US |
Affilliation | Universidade Federal de Viçosa. Departamento de Quimica. Viçosa, MG, Brazil | en_US |
Affilliation | Universidade Federal do Piauí. Programa de Pós-graduação em Química. Teresina, PI, Brazil | en_US |
Affilliation | Universidade Federal Fluminense. Instituto de Quimica. Niterói, RJ, Brazil | en_US |
Affilliation | Universidade Federal de Goiás. Instituto de Quimica. Sambambaia, GO, Brazil | en_US |
Affilliation | Universidade Federal de Goiás. Instituto de Quimica. Sambambaia, GO, Brazil | en_US |
Affilliation | Universidade Federal de Viçosa. Departamento de Fitopatologia. Viçosa, MG, Brazil | en_US |
Affilliation | Universidade Federal de Viçosa. Departamento de Fitopatologia. Viçosa, MG, Brazil | en_US |
Affilliation | Fundação Oswaldo Cruz. Instituto René Rachou. Laboratório de Química de Produtos Naturais Bioativos. Belo Horizonte, MG, Brasil | en_US |
Affilliation | Universidade Federal de Maringá. Departamento de Quimica. Maringá, PR, Brazil | en_US |
Affilliation | Universidade Federal de Viçosa. Departamento de Quimica. Viçosa, MG, Brazil | en_US |
Subject | Ugi 4-CR | en_US |
Subject | multicomponent reaction | en_US |
Subject | isocyanides | en_US |
Subject | herbicides | en_US |
Embargo date | 3100-12-31 | |