Design, Synthesis and Bioactivities of Novel Isoxazole-Containing Pyrazole Oxime Derivatives.

Hong Dai,Yujun Shi,Yuan Fang,Guoqing Jiang,Jian Shi,Siyu Sun,Wei Yao,Jia Chen

doi:10.3390/molecules22122000

Abstract

In this study, in order to find novel biologically active pyrazole oxime derivatives, twenty-eight new pyrazole oxime compounds containing a substituted isoxazole ring were synthesized and evaluated for their acaricidaland insecticidal activities. Bioassays exhibited that some target compounds indicated good acaricidal and insecticidal activities against Tetranychus cinnabarinus, Aphis medicaginis, Mythimna separata, and Nilaparvata lugens. Especially, compounds 9c, 9h, 9u, and 9v showed 100.00%, 90.56%, 90.78%, and 90.62% insecticidal activities against A. medicaginis at the concentration of 20 μg/mL, respectively, compounds 9k and 9u had 70.86% and 100.00% insecticidal activities against M. separata at 20 μg/mL, respectively.

Highlights

In the past few decades, heterocycles play a significant role in the research of agricultural and medicinal chemistry
We describe the design and synthesis of a number compounds with multiple biological activities
We describe the design and synthesis of of novel pyrazole oxime derivatives isoxazole

Summary

Introduction

In the past few decades, heterocycles play a significant role in the research of agricultural and medicinal chemistry. The isoxazole skeleton, a crucial type of nitrogen-containing heterocycle, has been used in pesticide and drug design because of their various biological activities, such as insecticidal [1,2,3], herbicidal [4,5,6], fungicidal [7], antiviral [8,9,10], and anticancer activities [11]. Sun et al reported several series of isoxazole compounds carrying benzoylurea moiety displaying perfect insecticidal activities [13]. Pyrazole oxime derivatives are one of the hotspots in the design of new drugs due to their broad spectrum of insecticidal [14,15], acaricidal [16], fungicidal [17], anti-TMV [18], and antitumor activities [19]. Fenpyroximate (Figure 1), an excellent acaricide containing a pyrazole oxime moiety, is used to control some phytophagous mites, such as Tetranychus urticae Koch and Polyphagotarsonemus latus Banks [20,21]

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Results

Conclusion