Synthesis, Biological Evaluation and In Silico Computational Studies of 7-Chloro-4-(1H-1,2,3-triazol-1-yl)quinoline Derivatives: Search for New Controlling Agents against Spodoptera frugiperda (Lepidoptera: Noctuidae) Larvae

Abstract

The insecticidal and antifeedant activities of five 7-chloro-4-(1H-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 LD50 values below 3 mg/g insect, and triazolyl-quinoline hybrid 6 showed an LD50 of 0.65 mg/g insect, making it 2-fold less potent than methomyl, which was used as a reference insecticide (LD50 = 0.34 mg/g insect). Compound 4 was the most active antifeedant derivative (CE50 = 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) (IC50 = 27.7 μg/mL) as well as low anti-ChE activity on S. frugiperda larvae homogenate (IC50 = 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.

Design, Synthesis, Crystal Structure, and Antimicrobial Evaluation of 6-Fluoroquinazolinylpiperidinyl-Containing 1,2,4-Triazole Mannich Base Derivatives against Phytopathogenic Bacteria and Fungi

“…On the basis of the above-mentioned considerations, herein we designed and synthesized a series of 6-fluoroquinazolinylpiperidinyl-bearing 1,2,4-triazole-5-thione Mannich base derivatives by the molecular hybridization approach (favorable for exerting synergistic effects on the bioactivity; , Figure ). All of the target compounds were assessed in detail for their in vitro antibacterial and antifungal efficacies against three types of phytopathogenic bacteria and six types of phytopathogenic fungi of great agricultural significance.…”

Insecticidal Activity of Organic Extracts of Solidago graminifolia and Its Main Metabolites (Quercetin and Chlorogenic Acid) against Spodoptera frugiperda: An In Vitro and In Silico Approach

“…Their biological cycle was followed until egg hatching was achieved. For the bioassays, 2-day-old neonate larvae were used for all treatments [ 7 ].…”

“…The phytochemical characteristics of this species provide the basis for investigation into inhibitory secondary metabolites of essential proteins for the survival of insect pests, such as acetylcholinesterase ( AChE ) [ 7 ]. The insecticidal effect is a minimally explored activity of this plant [ 8 , 9 ].…”

Advances in Control Strategies against Spodoptera frugiperda. A Review

“…Derivatives of 7-chloro-4-(1 H -1,2,3-triazol-1-yl) quinoline ( Figure 6 ) have been evaluated on the fourth instar of S. frugiperda to explore their insecticidal and antifeedant activity and acetylcholinesterase inhibition. This family of compounds has become a structure of interest for the search and design of new bioactive compounds in medicinal and agricultural chemistry [ 30 ]. The characteristics of each of the biological evaluations are listed in Table 1 .…”