| Autor: |
Rosado-Solano DN; Grupo de Investigaciones Ambientales para el Desarrollo Sostenible, Facultad de Química Ambiental , Universidad Santo Tomás , Bucaramanga A.A. 1076 , Colombia., Barón-Rodríguez MA; Grupo de Investigaciones Ambientales para el Desarrollo Sostenible, Facultad de Química Ambiental , Universidad Santo Tomás , Bucaramanga A.A. 1076 , Colombia., Sanabria Florez PL; Grupo de Investigaciones Ambientales para el Desarrollo Sostenible, Facultad de Química Ambiental , Universidad Santo Tomás , Bucaramanga A.A. 1076 , Colombia., Luna-Parada LK; Laboratorio de Química Orgánica y Biomolecular, CMN, Parque Tecnológico Guatiguará , Universidad Industrial de Santander , Km 2 vía Refugio , Piedecuesta , A.A. 681011 , Colombia., Puerto-Galvis CE; Laboratorio de Química Orgánica y Biomolecular, CMN, Parque Tecnológico Guatiguará , Universidad Industrial de Santander , Km 2 vía Refugio , Piedecuesta , A.A. 681011 , Colombia.; Laboratorio de Química Orgánica Aplicada , Universidad Manuela Beltrán , Cl. 33 # 26-34 , Bucaramanga , A.A. 680002 , Colombia., Zorro-González AF; Grupo de Investigaciones Ambientales para el Desarrollo Sostenible, Facultad de Química Ambiental , Universidad Santo Tomás , Bucaramanga A.A. 1076 , Colombia., Kouznetsov VV; Laboratorio de Química Orgánica y Biomolecular, CMN, Parque Tecnológico Guatiguará , Universidad Industrial de Santander , Km 2 vía Refugio , Piedecuesta , A.A. 681011 , Colombia., Vargas-Méndez LY; Grupo de Investigaciones Ambientales para el Desarrollo Sostenible, Facultad de Química Ambiental , Universidad Santo Tomás , Bucaramanga A.A. 1076 , Colombia. |
| Abstrakt: |
The insecticidal and antifeedant activities of five 7-chloro-4-(1 H -1,2,3-triazol-1-yl)quinoline derivatives were evaluated against the maize armyworm, Spodoptera frugiperda (J.E. Smith). These hybrids were prepared through a copper-catalyzed azide alkyne cycloaddition (CuAAC, known as a click reaction) and displayed larvicidal properties with LD 50 values below 3 mg/g insect, and triazolyl-quinoline hybrid 6 showed an LD 50 of 0.65 mg/g insect, making it 2-fold less potent than methomyl, which was used as a reference insecticide (LD 50 = 0.34 mg/g insect). Compound 4 was the most active antifeedant derivative (CE 50 = 162.1 μg/mL) with a good antifeedant index (56-79%) at concentrations of 250-1000 μg/mL. Additionally, triazolyl-quinoline hybrids 4 - 8 exhibited weak inhibitory activity against commercial acetylcholinesterase from Electrophorus electricus (electric-eel AChE) (IC 50 = 27.7 μg/mL) as well as low anti-ChE activity on S. frugiperda larvae homogenate (IC 50 = 68.4 μg/mL). Finally, molecular docking simulations suggested that hybrid 7 binds to the catalytic active site (CAS) of this enzyme and around the rim of the enzyme cavity, acting as a mixed (competitive and noncompetitive) inhibitor like methomyl. Triazolyl-quinolines 4 - 6 and 8 inhibit AChE by binding over the perimeter of the enzyme cavity, functioning as noncompetitive inhibitors. The results described in this work can help to identify lead triazole structures from click chemistry for the development of insecticide and deterrent products against S. frugiperda and related insect pests. |
