Design, Synthesis and Insecticidal Evaluation of Novel Pyrazolecarboxamides Containing Cyano Substituted N‐Pyridylpyrazole

Abstract

12 novel pyrazolecarboxamides containing cyano substituted N-pyridylpyrazole were synthesized, and their structures were characterized by 1 H NMR and HRMS techniques. Their evaluated insecticidal activities against oriental armyworm (Mythimna separata) indicated that the cyano-containing pyrazolecarboxamides exhibited moderate insecticidal activities. Compounds 6i and 6k showed comparable higher activity than corresponding anthranilic diamide 6m.

Synthesis, insecticidal activities, and structure–activity relationships of 1,3,4‐oxadiazole‐ring‐containing pyridylpyrazole‐4‐carboxamides as novel insecticides of the anthranilic diamide family

“…The structures of all the synthesized compounds were confirmed by 1 H nuclear magnetic resonance (NMR) spectroscopy, 13 C NMR spectroscopy, mass spectrometry (MS), and elemental analysis. The single peak in each 1 H NMR spectrum at 9.99-9.75 ppm was assigned to the aromatic amide hydrogen (O═C NH ).…”

“…The general chemical structure of an anthranilic diamide consists of a substituted benzene ring (A), an N-pyridylpyrazole amide group (B), and an aliphatic amide moiety (C) (Figure 2). Most previous studies have investigated substitution at either A [5,[8][9][10] or B [11][12][13][14][15][16]. In particular, the methyl group on the benzene ring has been substituted to produce a series of pyridine, pyrazole, formyl, and acetyl derivatives that exhibit insecticidal activities [1,17].…”

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

“…, M ) and simple amides (Fig. , N ) have previously been synthesized and found to display remarkable larvicidal activities against oriental armyworm, mosquito, diamondback moth, beet armyworm, etc . Surprisingly, some other kinds of such amide bond‐modified compounds, e.g.…”

“…2, N) have previously been synthesized and found to display remarkable larvicidal activities against oriental armyworm, mosquito, diamondback moth, beet armyworm, etc. [14][15][16][17] Surprisingly, some other kinds of such amide bond-modified compounds, e.g. hydrazines and -lactams with N-pyridylpyrazole characteristics (Fig.…”

Synthesis, biological evaluation and SAR analysis of novel poly‐heterocyclic compounds containing pyridylpyrazole group

“…, I),, as potent activators of the insect ryanodine receptor (RyR); N ‐pyridylpyrazole carboxamides with various simple substituents in the benzene ring of aniline were also found to have significant insecticidal properties towards oriental armyworm and diamondback moth (Fig. , II) , . Owing to the discovery of anthranilic diamides, studies related to the synthesis and the bioactivity of new compounds with similar structural characteristics have attracted considerable attention .…”