Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Modified N-Pyridylpyrazoles

Abstract

In order to look for novel insecticides targeting the ryanodine receptor, four new series of anthranilic diamides containing modified N-pyridylpyrazoles were designed and synthesized. All of the compounds were characterized and confirmed by (1)H NMR, (13)C NMR, and HRMS. The single crystal structure of 10c was determined by X-ray diffraction. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration, while compound 19 showed comparable higher activity at the concentration of 0.125 mg/L. The preliminary structure-activity relationship (SAR) was discussed.

Synthesis, Crystal Structure, and Biological Activity of Novel Anthranilic Diamide Insecticide Containing Propargyl Ether Group

“…There were many literatures reported for the modification of the anthranilic diamides [15][16][17]. Most modification was related to a variation of the substitution pattern in part of the aliphatic amide moiety.…”

“…The ethyl acetate solution was dried over magnesium sulfate and evaporated under reduced pressure, and the residual solid was washed with ether (3 × 30 mL) to afford intermediate 2-amino-5-chloro-3-methylbenzoic acid (5) Synthesis of intermediates 2-amino-5-chloro-3,N-dimethylbenzamide (6). 2-Amino-5-chloro-3,N-dimethyl-benzamide (6) was prepared according to the literature [15]. To a 100-mL round-bottomed flask was placed 2-amino-5-chloro-3-methylbenzoic acid (5) (3.7 g, 20 mmol) and then was added 50 mL of thionyl chloride.…”

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

“…3; benzo[d] [1,2,3] triazin-4(3H)-one compounds 3a−3e were also obtained. 17) Treatment of 2-amino-5-chloro-3-methylbenzoic acid with CDI and NH 3 ·H 2 O afforded amide 5, 7) which was conveniently dehydrated to nitrile 6 by the action of POCl 3.…”

“…The melting points and 1 H NMR data of all of the compounds were consistent with the literature. 7) Aromatic azides 2a−2e were prepared from the corresponding arylamines using standard azidation methods as shown in Fig. 3; benzo[d] [1,2,3] triazin-4(3H)-one compounds 3a−3e were also obtained.…”

“…2) Due to their outstanding insecticidal activity, unique mode of action and good environmental profiles, anthranilic diamide derivatives have attracted considerable attention in recent decades. [3][4][5][6][7][8][9][10][11] Recent modifications in the structure of chlorantraniliprole have mainly focused on three aspects: the N-pyridylpyrazole moiety, anthraniloyl moiety, and aliphatic amide moiety. Nevertheless, there have been some studies on the bridge between the pyridylpyrazole and the benzene ring in which these compounds exhibited good larvicidal activity, 12,13) indicating that the bridge moiety is still attractive for further modification.…”