Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a 5-Trifluoromethylpyridyl Moiety

Abstract

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.

Study of the Room‐Temperature Synthesis of Oxime Ethers by using a Super Base

“…Of the 24 oxime ethers obtained,1 1a re new compounds that are not described elsewhere in the literature. 1 Ha nd 13 CNMR analyses confirmed the structure of the final product. All compounds were obtained in ap ure form, which was also confirmed by the NMR spectra.M ass spectra analysis confirmed the presence of the appropriate products.…”

“…They are used in organic synthesis, providing valuable reagentst oo btain cis-1.2-aminoalcohols, [1] hydroxyloamines, [2] enantioselectives ynthesis of the amines, [3] and,u nder specific conditions in cyclization reactions, can lead to the formation of substituted heteroaromatic compounds. [4,5] However,m any oxime ethers are applicable as specifiedc ompounds with biological activity.T hey exhibit anticancer, [6] anti-aggregation, [7] antidepressant, [8,9] anticonvulsant, [10] antimicrobial, [11] antiviral, [12] acaricidal, [13] anti-protozoal, [14] and herbicidal [15] effects. There has also been research performed on the use of oxime ethers as fragrances.…”

“…The final products were received within 2min to 3h.I na ddition, the compounds do not requirec hromatographic separation. The structure elucida-tion of the titled compounds was performed by using 1 HNMR and 13 CNMR spectroscopy as wella sm ass spectrometry.T he presented method of synthesis foro xime ethers is environmentally friendly, because neither water cooling or heating of the reaction mixture/solvents (necessary for chromatographic purification) is required. The synthesis can be carried out very easily on al arge scale.…”

Lipophilicity Study of 1-(Benzofuran-2-yl)ethan-1-one Oxime and its Substituted O-Benzyl Ethers

“…3,4 Oxime ethers are interesting compounds due to their diverse biological activities. The compounds exhibit anticancer, 5 anticonvulsant, 6 antimicrobial, 7 antiparasitic 8 and acaricidal 9 activities. The most popular compound that contains oxime ether group is an oxiconazole ( Figure 1).…”

Synthesis, Crystal Structure, and DFT Study of Ethyl 1-(2-(Hydroxyimino)-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate

“…It has been found that they exhibit various biological activities that are often related to low toxicity and increase a great amount of beneficial influences on human health. Therefore, they have attracted wide interest for decades owing to their diverse biological properties such as insecticidal [1], acaricidal [2], antitumor [3][4][5], fungicidal [6], antiviral [7,8], antibacterial [9][10][11], COX inhibitory [12], and fluorescent [13,14] properties.…”