Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives.

Hong Dai,Yuan Fang,Huiyang Zhuang,Baojiang Dai,Yujun Shi,Linyu Ye

doi:10.3390/molecules201219811

Hong Dai, Yuan Fang + Show 4 more

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https://doi.org/10.3390/molecules201219811

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Abstract

In this study, in order to find novel biologically active pyrazole oxime compounds, a number of dichloro-allyloxy-phenol-containing pyrazole oximes were designed and synthesized according to the method of active group combination. All of the target compounds were confirmed by 1H-NMR, 13C-NMR and elemental analysis. In addition, bioassays showed that all of the newly synthesized compounds had no acaricidal activity against Tetranychus cinnabarinus and low insecticidal activity against Aphis craccivora at tested concentrations. However, most of them displayed excellent insecticidal activity against Oriental armyworm at a concentration of 500 μg/mL, and some designed compounds still exhibited potent insecticidal activity against Oriental armyworm even at the dose of 20 μg/mL, especially compounds 7f, 7n and 7p had 100%, 90% and 90% inhibition rates, respectively, which were comparable to that of the control pyridalyl.

Highlights

Pyrazole oximes are an important class of heterocyclic compounds which have drawn intense attention because of their good fungicidal [1,2], insecticidal [3,4,5], acaricidal [6], and anti-tobacco mosaic virus (TMV) activity [7]
Pyrazole oxime group can be used as an important skeleton in exploring novel bioactive molecules
A21s87d1isplayed in Table 1, all of the title compounds possessed no activities against Tetranychus cinnabarinus at a concentration of 500 μg/mL, and most of Molecules 2015, 20, 21870–21880

Summary

Introduction

Pyrazole oximes are an important class of heterocyclic compounds which have drawn intense attention because of their good fungicidal [1,2], insecticidal [3,4,5], acaricidal [6], and anti-tobacco mosaic virus (TMV) activity [7]. Pyridalyl (Figure 1), a novel dichloro-allyloxy-phenol insecticide, was discovered by Sumitomo Chemical Co., Ltd. and marketed in 2004 [12]. It displays good insecticidal activity against different lepidopterous pests on various crops such as cotton and vegetables, and exhibits no cross-resistance with other existing insecticides including synthetic pyrethroids, organic phosphates, benzoylureas and nicotinic insecticides [13,14]. Its biochemical mode of action is still unknown, while recent study

Methods

Discussion

Conclusion