Synthesis and biological evaluation of novel <i>N</i>-pyridylpyrazole derivatives containing 1,2,3-triazole moieties

Abstract

Based on the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazole derivatives containing 1,2,3-triazole moieties were designed and synthesized via Huisgen cycloaddition reaction. The insecticidal activities of the new compounds against the oriental armyworm (Mythimna separata) were evaluated, of which compound Ib with an Nisopropyl anthranilic amide moiety displayed 100% larvicidal activities against Mythimna separata at a concentration of 10 mg/L. Moreover, the fungicidal activities of some target compounds in vitro against five fungi at 50 µg⁄mL indicated that some compounds exhibited moderate fungicidal activities.

Crystal structure of 2-[(2-oxo-thiazolidine-3-carbonyl)sulfamoyl]-methy-benzoic acid methyl ester, C13H14N2O6S2

“…The herbicidal, fungicidal, insecticidal activities of the title compound were measured according to the reference method [4][5][6]. The results indicated that the title compound showed weak inhibitory activity against Fusarium oxysporum, Rhizoctonia solani, Gibberella zeae, Botryospuaeria berengeriana and Colletotrichum gossypii at 50 ppm, respectively.…”

Synthesis and Insecticidal Evaluation of Novel N‐pyridylpyrazole Derivatives Containing Diacylhydrazine/1,3,4‐Oxadiazole Moieties

“…Because agricultural pests can develop resistance rapidly all over the world, it is necessary to develop efficient insecticides with novel structures and modes of action . As a selective activator of the insect ryanodine receptor, chlorantraniliprole ( A , Scheme ) which has attracted considerable attention for decades because of its exceptional insecticidal activity on a broad spectrum and low mammalian toxicity . Recently, Li and Song et al .…”

“…Recently, Li and Song et al . have designed and synthesized series of novel N ‐pyridylpyrazole derivatives on the basis of the structure of chlorantraniliprole . Their results demonstrated that the modifications in the structure of chlorantraniliprole are still attractive.…”

Copper(I)‐Catalyzed Azide‐Alkyne Cycloaddition Microwave‐Assisted: Preparation of 7‐(4‐Substituted‐1H‐1,2,3‐Triazol‐1‐yl)‐Fluoroquinolones

“…‐ The 1,2,3 moiety does not occur in nature, although the synthetic molecules containing 1,2,3‐triazole unit show diverse biological activities including anti‐obesity, antiallergic, antibacterial, antiparasitic, herbicidal, fungicidal, and anti‐HIV 1,2,3‐triazole moieties are stable to metabolic degradation, oxidative/reductions conditions, and are capable of dipole‐dipole interactions and hydrogen bonding, which can be favourable in the binding of biomolecular targets and for solubility …”