Design, synthesis and insecticidal activities of N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives

Abstract

Insect ryanodine receptor is one of the promising targets for the development of novel insecticides. In order to search for potent insecticides targeting the ryanodine receptor (RyR), a series of novel diphenyl-1Hpyrazole derivatives with cyano substituent were designed and synthesized. Their insecticidal activities against diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the four concentrations. Among these compounds, N-(4-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-1-(4-fluorophenyl)-3-phenyl-1H-pyrazole-4-carboxamide (5g) showed 84% larvicidal activity against Plutella xylostella at the concentration of 0.1 mg L À1 . Molecular docking showed the predicted binding mode between 5g and protein receptor, which could suggest that the title compounds were the possible activators of insect RyR. Fig. 1 The products of insecticidal pyrazole derivatives.

Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity

“…In recent years, literature revealed that pyrazole derivatives had a wide range of biological activities, such as antibacterial [ 5 , 6 , 7 ], fungicidal [ 8 , 9 , 10 ], insecticidal [ 10 , 11 , 12 , 13 ], antiviral [ 14 , 15 ], and herbicidal [ 16 , 17 ] activities. In our previous work, we reported a series of pyrazole derivatives which had better insecticidal activity against Plutella xylostella [ 18 ].…”

Synthesis, Structure, and Antifungal Activities of 3-(Difluoromethyl)-Pyrazole-4-Carboxylic Oxime Ester Derivatives

“…Nitrogen-linked heterocycles are an important skeleton in synthetic chemistry or natural product chemistry because of their diversity of structure and activity [1][2][3][4][5]. Among these nitrogen-linked heterocycles; pyrazole compounds, especially pyrazole carboxamide compounds, exhibit diverse activity, with examples possessing nematocidal [6][7][8][9][10], insecticidal [11,12], antibacterial [13], IRAK4 inhibitor [14], antiproliferative [15], antimicrobial [16], immunomodulatory [17], and fungicidal activity [18][19][20]. Some pyrazole amide compounds have been commercialized as fungicides [21] or insecticides [22].…”

Synthesis Candidates Herbicide Through Optimization Quinclorac Containing 3-Methyl-1H-pyrazol-5-yl

“…Pyrazole-containing compounds have played an important role in the development of heterocyclic agrochemicals because the pyrazole structure enables multidirectional transformations, and the introduction of different substituents on pyrazole provides a diversity of structures (Fu et al, 2017;Jiao et al, 2019;Fu et al, 2020). Furthermore, as pyrazole-containing compounds exhibit various biological activities, high selectivities, and low toxicities, they have received attention for the development of new pesticides in recent years (Du et al, 2015;Lv et al, 2015;Yao et al, 2017;Zhao et al, 2019), for example, pyrazosulfuron, azimsulfuron, benzofenap, and pyrazolate. Several pyrazole-containing agriculture chemicals have been commercialized.…”