Abstract
In this study, in order to find novel biologically active pyrazole oxime compounds, a series of pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety were synthesized. Preliminary bioassays indicated that most title compounds were found to display good to excellent acaricidal activity against Tetranychus cinnabarinus at a concentration of 200 μg/mL, and some designed compounds still showed excellent acaricidal activity against Tetranychus cinnabarinus at the concentration of 10 μg/mL, especially since the inhibition rates of compounds 8e, 8f, 8l, 8m, 8n, 8p, and 8q were all 100.00%. Interestingly, some target compounds exhibited moderate to good insecticidal activities against Plutella xylostella and Aphis craccivora at a concentration of 200 μg/mL; furthermore, compounds 8e and 8l possessed outstanding insecticidal activities against Plutella xylostella under the concentration of 50 μg/mL.
Highlights
Agrochemicals, together with genetically modified insect-resistant crops and biological plant protection methods, prevent severe harvest losses caused by phytophagous insects and mites [1,2,3].Over the past decades, a great variety of chemical pesticides have been developed and used in the protection of crops, among which pyrazole derivatives occupy a considerable proportion in insecticides, germicides and acaricides [4,5,6,7]
A great variety of chemical pesticides have been developed and used in the protection of crops, among which pyrazole derivatives occupy a considerable proportion in insecticides, germicides and acaricides [4,5,6,7]
Fenpyroximate is structurally characterized by the unique 4-pyrazole oxime, which is recognized as an irreplaceable pharmacophore for acaricidal or insecticidal activities
Summary
A great variety of chemical pesticides have been developed and used in the protection of crops, among which pyrazole derivatives occupy a considerable proportion in insecticides, germicides and acaricides [4,5,6,7]. Nihon Nohyaku Co. in 1991, Fenpyroximate (Figure 1) has been widely used in protecting various crops due to its high efficiency against agricultural mites such as Polyphagotarsonemus latus Banks and Tetranychus urticae Koch, and its low toxicity to mammals [8]. Fenpyroximate is structurally characterized by the unique 4-pyrazole oxime, which is recognized as an irreplaceable pharmacophore for acaricidal or insecticidal activities. In the process of developing new Fenpyroximate derivatives, modification of phenyl B (Figure 1) and its substituents was mainly concentrated on with the 4-pyrazole oxime moiety retained. Dai and coworkers reported some acaricidal or insecticidal Fenpyroximate mimics that were obtained by replacing the phenyl
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