Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides

The pyrazole core has been recognized by their biological properties and included in the synthesis of modern agrochemicals. Part of these studies consists of making structural modifications to pesticides for commercial purposes to increase efficacy. In this article, we present the synthesis of four...

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Autores:
González-López, Edwin
Tipo de recurso:
Fecha de publicación:
2020
Institución:
Universidad del Atlántico
Repositorio:
Repositorio Uniatlantico
Idioma:
eng
OAI Identifier:
oai:repositorio.uniatlantico.edu.co:20.500.12834/923
Acceso en línea:
https://hdl.handle.net/20.500.12834/923
Palabra clave:
agrochemicals, antifungal agent, Colletotrichum gloeosporioides, nitrogen heterocycles, pyrazole carboxamide
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc/4.0/
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dc.title.spa.fl_str_mv Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
title Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
spellingShingle Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
agrochemicals, antifungal agent, Colletotrichum gloeosporioides, nitrogen heterocycles, pyrazole carboxamide
title_short Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
title_full Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
title_fullStr Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
title_full_unstemmed Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
title_sort Synthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioides
dc.creator.fl_str_mv González-López, Edwin
dc.contributor.author.none.fl_str_mv González-López, Edwin
dc.contributor.other.none.fl_str_mv León-Jaramillo, Jhair
Trilleras, Jorge
Grande-Tovar, Carlos D.
Peralta-Ruiz, Yeimmy
Quiroga, Jairo
dc.subject.keywords.spa.fl_str_mv agrochemicals, antifungal agent, Colletotrichum gloeosporioides, nitrogen heterocycles, pyrazole carboxamide
topic agrochemicals, antifungal agent, Colletotrichum gloeosporioides, nitrogen heterocycles, pyrazole carboxamide
description The pyrazole core has been recognized by their biological properties and included in the synthesis of modern agrochemicals. Part of these studies consists of making structural modifications to pesticides for commercial purposes to increase efficacy. In this article, we present the synthesis of four new pyrazol-4-carboxamide 8a-8d derivatives (PCD), through a four-step synthetic protocol, starting with edaravone 1 and primary amines like benzo-fused, aliphatic, and hydrazines, through a process of low environmental impact. Synthesized derivatives were evaluated against one fungal strain of Colletotrichum gloeosporioides BA3, fungus that causes several losses to farmers around the world, through in vitro sensitivity tests. The compound 8c showed better inhibiting behavior against Colletotrichum gloeosporioides BA3, inducing a lag phase of almost 2.77 days. These results were obtained via Gompertz modeling, for the first time reported for biological evaluation of pyrazole-carboxamide derivatives against Colletotrichum gloeosporioides.
publishDate 2020
dc.date.issued.none.fl_str_mv 2020-05-19
dc.date.submitted.none.fl_str_mv 2020-01-31
dc.date.accessioned.none.fl_str_mv 2022-11-15T21:01:48Z
dc.date.available.none.fl_str_mv 2022-11-15T21:01:48Z
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dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/article
dc.type.hasVersion.spa.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.spa.spa.fl_str_mv Artículo
status_str publishedVersion
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12834/923
dc.identifier.doi.none.fl_str_mv 10.21577/0103-5053.20200092
dc.identifier.instname.spa.fl_str_mv Universidad del Atlántico
dc.identifier.reponame.spa.fl_str_mv Repositorio Universidad del Atlántico
url https://hdl.handle.net/20.500.12834/923
identifier_str_mv 10.21577/0103-5053.20200092
Universidad del Atlántico
Repositorio Universidad del Atlántico
dc.language.iso.spa.fl_str_mv eng
language eng
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eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.place.spa.fl_str_mv Barranquilla
dc.publisher.discipline.spa.fl_str_mv Química
dc.publisher.sede.spa.fl_str_mv Sede Norte
dc.source.spa.fl_str_mv Sociedade Brasileira de Química
institution Universidad del Atlántico
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spelling González-López, Edwin603c75f6-10fe-40e9-bd5b-3157cd0b8074León-Jaramillo, JhairTrilleras, JorgeGrande-Tovar, Carlos D.Peralta-Ruiz, YeimmyQuiroga, Jairo2022-11-15T21:01:48Z2022-11-15T21:01:48Z2020-05-192020-01-31https://hdl.handle.net/20.500.12834/92310.21577/0103-5053.20200092Universidad del AtlánticoRepositorio Universidad del AtlánticoThe pyrazole core has been recognized by their biological properties and included in the synthesis of modern agrochemicals. Part of these studies consists of making structural modifications to pesticides for commercial purposes to increase efficacy. In this article, we present the synthesis of four new pyrazol-4-carboxamide 8a-8d derivatives (PCD), through a four-step synthetic protocol, starting with edaravone 1 and primary amines like benzo-fused, aliphatic, and hydrazines, through a process of low environmental impact. Synthesized derivatives were evaluated against one fungal strain of Colletotrichum gloeosporioides BA3, fungus that causes several losses to farmers around the world, through in vitro sensitivity tests. The compound 8c showed better inhibiting behavior against Colletotrichum gloeosporioides BA3, inducing a lag phase of almost 2.77 days. These results were obtained via Gompertz modeling, for the first time reported for biological evaluation of pyrazole-carboxamide derivatives against Colletotrichum gloeosporioides.application/pdfenghttp://creativecommons.org/licenses/by-nc/4.0/Attribution-NonCommercial 4.0 Internationalinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Sociedade Brasileira de QuímicaSynthesis and Evaluation of the Fungal Activity of New Pyrazole-Carboxamides against Colletotrichum gloeosporioidesPúblico generalagrochemicals, antifungal agent, Colletotrichum gloeosporioides, nitrogen heterocycles, pyrazole carboxamideinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArtículohttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1BarranquillaQuímicaSede Norte1. Thuy, G. L.; Abhijit, K.; Atanu, G.; Nghi, H.; Nguyen, S. P.; Yaqing, J.; Banfeng, R.; Lian, X.; Fei, H.; Keiser, J.; Hofmann, A.; Chang, B. C. H.; García-Bustos, J.; Wells, T. N. C.; Palmer, M. J.; Jabbar, A.; Gasser, R. B.; Baell, J. B.; J. Med. Chem. 2019, 62, 1036.2. Zhang, J.; Peng, J. F.; Wang, T.; Kang, Y.; Jing, S.; Zhang, Z.-T.; Mol. Diversity 2017, 21, 317.3. Khan, M. F.; Alam, M. M.; Verma, G.; Akhtar, W.; Akhter, M.; Shaquiquzzaman, M.; Eur. J. Med. Chem. 2016, 120, 170.4. Havrylyuk, D.; Roman, O.; Lesyk, R.; Eur. J. Med. Chem. 2016, 113, 145.5. Küçükgüzel, Ş. G.; Şenkardeş, S.; Eur. J. Med. Chem. 2015, 97, 7866. Xu, C.; Li, M.; Zhou, Z.; Li, J.; Chen, D.; Duan, Y.; Zhou, M.; Toxins 2019, 11, 272.7. Kumar, A.; Fernandes, J.; Kumap, P.; Orient. J. Chem. 2014, 30, 1993.8. Xiang, Y.; Zhang, Y.; Wang, C.; Liu, S.; Liao, X.; Pestic. Biochem. Physiol. 2017, 147, 32.9. Pinto, L. S. R. C.; Azevedo, J. L.; Pereira, J. O.; Vieira, M. L. C.; Labate, C. A.; New Phytol. 2000, 147, 609.10. Saremi, H.; Okhovvat, S. M.; Ashrafi, S. J.; Afr. J. Biotechnol. 2011, 10, 18391.11. Riera, N.; Ramirez-Villacis, D.; Barriga-Medina, N.; AlvarezSantana, J.; Herrera, K.; Ruales, C.; Leon-Reyes, A.; Plant Dis. 2019, 103, 76312. Pardo-De La Hoz, C. J.; Calderón, C.; Rincón, A. M.; Cárdenas, M.; Danies, G.; López-Kleine, L.; Jiménez, P.; Plant Pathol. 2016, 65, 227.13. Garrigues, S.; Gandía, M.; Marcos, J. F.; Appl. Microbiol. Biotechnol. 2016, 100, 224314. Guan, A.; Liu, C.; Yang, X.; Dekeyser, M.; Chem. Rev. 2014, 114, 707915. Vilaplana, R.; Chicaiza, G.; Vaca, C.; Valencia-Chamorro, S.; Crop Prot. 2020, 128, 105007.16. Quintero Mercado, A.; Dangon-Bernier, F.; Páez-Redondo, A.; Rev. Acad. Colomb. Cienc. Exactas, Fis. Nat. 2019, 43, 6517. Zhang, A.; Zhou, J.; Tao, K.; Hou, T.; Jin, H.; Bioorg. Med. Chem. Lett. 2018, 28, 304218. Keri, R. S.; Chand, K.; Ramakrishnappa, T.; Nagaraja, B. M.; Arch. Pharm. 2015, 348, 299.19. Jeschke, P.; Pest Manage. Sci. 2010, 66, 10.20. Peng, H.; Zhang, P.; Bilal, M.; Wang, W.; Hu, H.; Zhang, X.; Microb. Cell Fact. 2018, 17, 117.21. Juliatti, F.; Polloni, L.; de Morais, T.; Zacarias, S.; Silva, E.; Juliatti, B.; Biosci. J. 2017, 33, 933.22. Szmuszkovicz, J.; Chidester, C. G.; Laurian, L. G.; Scahill, T. A.; J. Org. Chem. 1986, 51, 500223. Huang, D.; Liu, A.; Liu, W.; Liu, X.; Ren, Y.; Zheng, X.; Pei, H.; Xiang, J.; Huang, M.; Wang, X.; Heterocycl. Commun. 2017, 23, 45524. Hranjec, M.; Sovic, I.; Ratkaj, I.; Pavlovic, G.; Ilic, N.; Valjalo, L.; Pavelic, K.; Pavelic, S. K.; Karminski-Zamola, G.; Eur. J. Med. Chem. 2013, 59, 11125. Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M.; Bioorg. Med. Chem. 2016, 24, 31726. Mu, J.-X.; Shi, Y.-X.; Yang, M.-Y.; Sun, Z.-H.; Liu, X.-H.; Li, B.-J.; Sun, N.-B.; Molecules 2016, 21, 6827. Wu, J.; Shi, Q.; Chen, Z.; He, M.; Jin, L.; Hu, D.; Molecules 2012, 17, 5139.28. Zhao, D.; Sun, B.; Ren, J.; Li, F.; Song, S.; Lv, X.; Hao, C.; Cheng, M.; Bioorg. Med. Chem. 2015, 23, 135629. Sun, B.; Liu, K.; Han, J.; Zhao, L.-Y.; Su, X.; Lin, B.; Zhao, D.-M.; Cheng, M.-S.; Bioorg. Med. Chem. 2015, 23, 6763.30. Abdel-Wahab, B. F.; Khidre, R. E.; Farahat, A. A.; ARKIVOC 2011, i, 19631. Abu-Zaied, M. A.; El-Telbani, E. M.; Elgemeie, G. H.; Nawwar, G. A. M.; Eur. J. Med. Chem. 2011, 46, 229.32. Kasımogulları, R.; Arslan, B. S.; J. Heterocycl. Chem. 2010, 47, 104033. Kasımogulları, R.; Duran, H.; Yaglıoglu, A. S.; Mert, S.; Demirtas, I.; Monatsh. Chem. 2015, 146, 1743.34. Minnelli, C.; Laudadio, E.; Galeazzi, R.; Rusciano, D.; Armeni, T.; Stipa, P.; Cantarini, M.; Mobbili, G.; Antioxidants 2019, 8, 258.35. Ali, Z. K.; Baker, D. E.; Hosp. Pharm. 2017, 52, 732.36. Xiao, J.-J.; Liao, M.; Chu, M.-J.; Ren, Z.-L.; Zhang, X.; Lv, X.-W.; Cao, H.-Q.; Molecules 2015, 20, 807.37. Trilleras, J.; Quiroga, J.; Cobo, J.; Low, J. N.; Glidewell, C.; Acta Crystallogr., Sect. E: Crystallogr. Commun. 2005, 61, 105538. Liu, X.; Qiao, L.; Zhai, Z.; Cai, P.; Charles, L.; Tan, C.; Weng, J.; Wu, H.; Pest Manage. Sci. 2019, 75, 2892.39. Grande-Tovar, C. D.; Chaves-López, C.; Viuda-Martos, M.; Serio, A.; Delgado-Ospina, J.; Pérez-Alvarez, J.A.; Ospina, N.; la Tora, S.; Palmieri, S.; Paparella, A.; Ind. Crop. Prod. 2016, 87, 315.40. Apaydın, S.; Török, M.; Bioorg. Med. Chem. Lett. 2019, 29, 2042.41. Cai, N.; Liu, C.; Feng, Z.; Li, X.; Qi, Z.; Ji, M.; Qin, P.; Ahmed, W.; Cui, Z.; Molecules 2018, 23, 720.42. Zoumpoulakis, P.; Camoutsis, C.; Pairas, G.; Soković, M.; Glamočlija, J.; Potamitis, C.; Pitsas, A.; Bioorg. Med. Chem. 2012, 20, 1569.43. Oliveira, P. D. L.; de Oliveira, K. Á. R.; Vieira, W. A. S.; Câmara, M. P. S.; de Souza, L. L.; Int. J. Food Microbiol. 2018, 266, 87.44. Zwietering, M. H.; Jongenburger, I.; Rombouts, F. M.; van’t Riet, K.; Appl. Environ. Microbiol. 1990, 56, 1875.45. 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