Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.colsurfa.2022.130470 http://hdl.handle.net/11449/249346 |
Resumo: | Atrazine (ATZ) formulations are used to control a broad spectrum of weeds. The combination of ATZ with macromolecular systems, such as cyclodextrins (CDs), can improve its usefulness and herbicide efficacy related to the controlled release of the active ingredient. In this study, inclusion complexes of ATZ in CD and hybrid cyclodextrin-silica materials (CDSI) were prepared and characterized. Infrared spectral analysis of the inclusion compounds, concomitant with the suppression of the endothermic differential scanning calorimetry (DSC) peaks related to the fusion temperature of ATZ, confirmed the inclusion of ATZ in the functionalized and nonfunctionalized oligosaccharides. The linear increase in ATZ solubilization with the increasing addition of CD indicated that the inclusion stoichiometry was 1:1 in all studied systems. The increase in solubilization of the herbicide was approximately 1.3 times for α-CD and γ-CD, which had association constants of 20.3 and 13.4 L mol−1, respectively. The increase in solubility for α-CDSI and γ-CDSI was 3.3 and 2.7-fold, and the association constants were 161.1 and 111.1 L mol−1, respectively. Molecular mechanics (MM) calculations were performed using the force fields MM3* and AMBER*, and the results indicated that the most stable conformations resulted from the penetration of ATZ through the narrower cavity of the CDs. The MD calculations indicated three possible orientations for ATZ in the α-CD cavity, while for γ-CD the amplitude of the standard deviation of the energy values made it impossible to select a more favorable orientation. The ATZ release profile was affected by complexation. Over 22 h, more than 50% of noncomplexed ATZ was released, while for the complexes, less than 20% was released. The complexation, as well as the commercial formulation, provided variations in the development of Brassica juncea seedlings for the layers with higher concentrations of ATZ, thus agreeing with soil layer mobility studies indicated that complexation did not increase the leaching capacity of ATZ, which was mainly distributed in the upper soil layers, where it may be more available for herbicide control functions. |
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Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soilAtrazineControlled releaseHerbicideInclusion complexSoil distributionWater solubilityAtrazine (ATZ) formulations are used to control a broad spectrum of weeds. The combination of ATZ with macromolecular systems, such as cyclodextrins (CDs), can improve its usefulness and herbicide efficacy related to the controlled release of the active ingredient. In this study, inclusion complexes of ATZ in CD and hybrid cyclodextrin-silica materials (CDSI) were prepared and characterized. Infrared spectral analysis of the inclusion compounds, concomitant with the suppression of the endothermic differential scanning calorimetry (DSC) peaks related to the fusion temperature of ATZ, confirmed the inclusion of ATZ in the functionalized and nonfunctionalized oligosaccharides. The linear increase in ATZ solubilization with the increasing addition of CD indicated that the inclusion stoichiometry was 1:1 in all studied systems. The increase in solubilization of the herbicide was approximately 1.3 times for α-CD and γ-CD, which had association constants of 20.3 and 13.4 L mol−1, respectively. The increase in solubility for α-CDSI and γ-CDSI was 3.3 and 2.7-fold, and the association constants were 161.1 and 111.1 L mol−1, respectively. Molecular mechanics (MM) calculations were performed using the force fields MM3* and AMBER*, and the results indicated that the most stable conformations resulted from the penetration of ATZ through the narrower cavity of the CDs. The MD calculations indicated three possible orientations for ATZ in the α-CD cavity, while for γ-CD the amplitude of the standard deviation of the energy values made it impossible to select a more favorable orientation. The ATZ release profile was affected by complexation. Over 22 h, more than 50% of noncomplexed ATZ was released, while for the complexes, less than 20% was released. The complexation, as well as the commercial formulation, provided variations in the development of Brassica juncea seedlings for the layers with higher concentrations of ATZ, thus agreeing with soil layer mobility studies indicated that complexation did not increase the leaching capacity of ATZ, which was mainly distributed in the upper soil layers, where it may be more available for herbicide control functions.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de Minas Gerais (FAPEMIG)Chemistry Department Universidade Federal de Lavras Campus Universitário s/n, MGInstitute of Science and Technology São Paulo State University, Av. Três de Março 511, SPHealth Science Institute Universidade Federal da Bahia, Av. Reitor Miguel Calmon, BADepartment of Chemistry Universitat Autònoma de BarcelonaInstitute of Science and Technology São Paulo State University, Av. Três de Março 511, SPFAPESP: #2017/21004–5FAPESP: #2018/23608–8CAPES: A107/2013FAPEMIG: APQ 00687–13Universidade Federal de Lavras (UFLA)Universidade Estadual Paulista (UNESP)Universidade Federal da Bahia (UFBA)Universitat Autònoma de BarcelonaBragança Carvalho, Lucas [UNESP]Abreu Venceslau, Adneia de FátimaLuz Ambrosio Breisch, DanielaFernandes Fraceto, Leonardo [UNESP]Jaime, CarlosMatos Alves Pinto, Luciana2023-07-29T15:13:35Z2023-07-29T15:13:35Z2023-01-05info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.colsurfa.2022.130470Colloids and Surfaces A: Physicochemical and Engineering Aspects, v. 656.1873-43590927-7757http://hdl.handle.net/11449/24934610.1016/j.colsurfa.2022.1304702-s2.0-85141474104Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengColloids and Surfaces A: Physicochemical and Engineering Aspectsinfo:eu-repo/semantics/openAccess2023-07-29T15:13:35Zoai:repositorio.unesp.br:11449/249346Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T20:13:21.551580Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
title |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
spellingShingle |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil Bragança Carvalho, Lucas [UNESP] Atrazine Controlled release Herbicide Inclusion complex Soil distribution Water solubility |
title_short |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
title_full |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
title_fullStr |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
title_full_unstemmed |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
title_sort |
Heterocyclic agrochemical hosted by cyclodextrin and hybrid cyclodextrin-silica materials: Characterization, release behavior, and mobility in soil |
author |
Bragança Carvalho, Lucas [UNESP] |
author_facet |
Bragança Carvalho, Lucas [UNESP] Abreu Venceslau, Adneia de Fátima Luz Ambrosio Breisch, Daniela Fernandes Fraceto, Leonardo [UNESP] Jaime, Carlos Matos Alves Pinto, Luciana |
author_role |
author |
author2 |
Abreu Venceslau, Adneia de Fátima Luz Ambrosio Breisch, Daniela Fernandes Fraceto, Leonardo [UNESP] Jaime, Carlos Matos Alves Pinto, Luciana |
author2_role |
author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Federal de Lavras (UFLA) Universidade Estadual Paulista (UNESP) Universidade Federal da Bahia (UFBA) Universitat Autònoma de Barcelona |
dc.contributor.author.fl_str_mv |
Bragança Carvalho, Lucas [UNESP] Abreu Venceslau, Adneia de Fátima Luz Ambrosio Breisch, Daniela Fernandes Fraceto, Leonardo [UNESP] Jaime, Carlos Matos Alves Pinto, Luciana |
dc.subject.por.fl_str_mv |
Atrazine Controlled release Herbicide Inclusion complex Soil distribution Water solubility |
topic |
Atrazine Controlled release Herbicide Inclusion complex Soil distribution Water solubility |
description |
Atrazine (ATZ) formulations are used to control a broad spectrum of weeds. The combination of ATZ with macromolecular systems, such as cyclodextrins (CDs), can improve its usefulness and herbicide efficacy related to the controlled release of the active ingredient. In this study, inclusion complexes of ATZ in CD and hybrid cyclodextrin-silica materials (CDSI) were prepared and characterized. Infrared spectral analysis of the inclusion compounds, concomitant with the suppression of the endothermic differential scanning calorimetry (DSC) peaks related to the fusion temperature of ATZ, confirmed the inclusion of ATZ in the functionalized and nonfunctionalized oligosaccharides. The linear increase in ATZ solubilization with the increasing addition of CD indicated that the inclusion stoichiometry was 1:1 in all studied systems. The increase in solubilization of the herbicide was approximately 1.3 times for α-CD and γ-CD, which had association constants of 20.3 and 13.4 L mol−1, respectively. The increase in solubility for α-CDSI and γ-CDSI was 3.3 and 2.7-fold, and the association constants were 161.1 and 111.1 L mol−1, respectively. Molecular mechanics (MM) calculations were performed using the force fields MM3* and AMBER*, and the results indicated that the most stable conformations resulted from the penetration of ATZ through the narrower cavity of the CDs. The MD calculations indicated three possible orientations for ATZ in the α-CD cavity, while for γ-CD the amplitude of the standard deviation of the energy values made it impossible to select a more favorable orientation. The ATZ release profile was affected by complexation. Over 22 h, more than 50% of noncomplexed ATZ was released, while for the complexes, less than 20% was released. The complexation, as well as the commercial formulation, provided variations in the development of Brassica juncea seedlings for the layers with higher concentrations of ATZ, thus agreeing with soil layer mobility studies indicated that complexation did not increase the leaching capacity of ATZ, which was mainly distributed in the upper soil layers, where it may be more available for herbicide control functions. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-07-29T15:13:35Z 2023-07-29T15:13:35Z 2023-01-05 |
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 |
http://dx.doi.org/10.1016/j.colsurfa.2022.130470 Colloids and Surfaces A: Physicochemical and Engineering Aspects, v. 656. 1873-4359 0927-7757 http://hdl.handle.net/11449/249346 10.1016/j.colsurfa.2022.130470 2-s2.0-85141474104 |
url |
http://dx.doi.org/10.1016/j.colsurfa.2022.130470 http://hdl.handle.net/11449/249346 |
identifier_str_mv |
Colloids and Surfaces A: Physicochemical and Engineering Aspects, v. 656. 1873-4359 0927-7757 10.1016/j.colsurfa.2022.130470 2-s2.0-85141474104 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Colloids and Surfaces A: Physicochemical and Engineering Aspects |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808129174218473472 |