Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N -H/CH 3 -1 H -Pyrazole
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doi: 10.1007/s40242-020-9037-1
Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH3-1H-Pyrazole ZHANG Xiulan1*, ZHANG Huan1, LIU Jingbo2, XIONG Lixia2 and LI Zhengming2* 1. College of Science, Tianjin University of Science & Technology, Tianjin 300457, P. R. China; 2. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China Abstract In order to systematically study the structure-activity relationship of anthranilic diamides and develop insecticides with simple structure and high efficiency, a series of novel anthranilic diamides containing N-H/CH3-1H-pyrazole was designed and synthesized. Their chemical structures were characterized by 1H NMR spectra, high resolution mass spectrometry(HRMS) or 13C NMR spectra. The preliminary bioassay results indicated that all title compounds displayed moderate insecticidal activity against oriental armyworm(Mythimna separata) at 200 mg/L and fungicidal activities against six kinds of fungi at 50 mg/L, especially compound 5i showed 50% insecticidal activity at 25 mg/L. In addition, some compounds exhibited certain antitumor activities. It was demonstrated that the introduction of CH 3 group into pyrazole ring was superior to H for the insecticidal activity. Keywords Anthranilic diamide; Insecticidal activity; Fungicidal activity; Antitumor activity
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Introduction
At present, diamide insecticides, which act on Ryanodine receptor(RyR) have become research hotspot in agricultural pesticides field[1,2]. They are mainly divided into two categories: phthalic diamides and anthranilic diamides, represented with flubendiamide and chlorantraniliprole, respectively. Owing to the more broad-spectrum[3] than flubendiamide, ovicidal action and certain systematic property, researchers prefer to develop new anthranilic diamides. A lot of modifications in the benzene ring part, bridge bond part and pyridyl pyrazole part in the lead structure have been developed. And the modifications of pyridyl pyrazole part mainly focused on changing the substituent in the 3-pyrazole, such as oxime ether[4], ether[5], trifluoromethyl[6], heterocyclic ring[7], and sulfonate[8], most of which retained the pyridyl group. In fact, the introduction of pyridine ring into the structure is not only pollutional in synthesis, but also unfavorable to derivatization. Researches had proved that N-H/CH3-1H-pyrazole-carboxamide derivates possessed extensive biological activities, especially insecticidal activity[9—13], bactericidal activity[14—18], acaricidal activity[19] and antitumor activity[20—23], and some representative compounds(A―F) are shown in Fig.1. In order to systematically study the structure-activity relationship of anthranilic diamides and develop insecticides with simple structure and high efficiency, pyridyl group was firstly removed from pyrazole ring in chlorantraniliprole to give compounds 5a―5h. In further exploration, compounds 5i―5p were synthesized by replacing pyridyl group in chlorant
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