904733-74-0Relevant academic research and scientific papers
Fragmenlt Recombination Design, Synthesis, and Safener Activity of Novel Ester-Substituted Pyrazole Derivatives
Fu, Ying,Gao, Shuang,Jia, Ling,Ye, Fei,Zhang, Yuan-Yuan,Zhao, Li-Xia
, p. 8366 - 8379 (2021/08/20)
Fenoxaprop-p-ethyl (FE), a type of acetyl-CoA carboxylase (ACCase) inhibitor, has been extensively applied to a variety of crop plants. It can cause damage to wheat (Triticum aestivum) even resulting in the death of the crop. On the prerequisite of not reducing herbicidal efficiency on target weed species, herbicide safeners selectively protect crops from herbicide injury. Based on fragment splicing, a series of novel substituted pyrazole derivatives was designed to ultimately address the phytotoxicity to wheat caused by FE. The title compounds were synthesized in a one-pot way and characterized via infrared spectroscopy, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. The bioactivity assay proved that the FE phytotoxicity to wheat could be reduced by most of the title compounds. The molecular docking model indicated that compound IV-21 prevented fenoxaprop acid (FA) from reaching or acting with ACCase. The absorption, distribution, metabolism, excretion, and toxicity predictions demonstrated that compound IV-21 exhibited superior pharmacokinetic properties to the commercialized safener mefenpyr-diethyl. The current work revealed that a series of newly substituted pyrazole derivatives presented strong herbicide safener activity in wheat. This may serve as a potential candidate structure to contribute to the further protection of wheat from herbicide injury.
Regioselective Synthesis of 3-Trifluoromethylpyrazole by Coupling of Aldehydes, Sulfonyl Hydrazides, and 2-Bromo-3,3,3-trifluoropropene
Zhu, Chuanle,Zeng, Hao,Liu, Chi,Cai, Yingying,Fang, Xiaojie,Jiang, Huanfeng
supporting information, p. 809 - 813 (2020/02/04)
A general and practical strategy for 3-trifluoromethylpyrazole synthesis is reported that occurs by the three-component coupling of environmentally friendly and large-tonnage industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP), aldehydes, and sulfonyl hydrazides. This highly regioselective three-component reaction is metal-free, catalyst-free, and operationally simple and features mild conditions, a broad substrate scope, high yields, and valuable functional group tolerance. Remarkably, the reactions could be performed on a 100 mmol scale and smoothly afforded the key intermediates for the synthesis of celecoxib, mavacoxib, SC-560, and AS-136A. Preliminary mechanism studies indicated that a 1,3-hydrogen atom transfer process was involved in this transformation.
Trifluoromethyl substituted pyrazole derivative as 3- well as synthesis method and application thereof (by machine translation)
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Paragraph 0224-0234, (2019/12/31)
The invention belongs to, the technical field. of synthesis of medical materials, 3 - and particularly, 2 - relates to a method for mixing and reacting a compound with, an, 2 - organic solvent I through Colecoxib a, method of mixing reaction with an organ
An efficient route to 3-trifluoromethylpyrazole via cyclization/1,5-H shift and its applications in the synthesis of bioactive compounds
Wang, Yongdong,Han, Jing,Chen, Jie,Cao, Weiguo
, p. 8256 - 8262 (2015/10/05)
A methodology for regioselective synthesis of 3-trifluoromethylpyrazole from the reaction of trifluoromethyl alkenone and tosylhydrazone has been developed. The reaction was proposed to proceed through a tandem cyclization and 1,5-H shift reaction, which can be applied to the synthesis of bioactive compounds like Celecoxib, Mavacoxib, and SC-560.
Synthesis and insecticidal evaluation of novel anthranilic diamides containing N-substitued nitrophenylpyrazole
Zhang, Xiulan,Li, Yuxin,Ma, Jinlong,Zhu, Hongwei,Wang, Baolei,Mao, Mingzhen,Xiong, Lixia,Li, Yongqiang,Li, Zhengming
, p. 186 - 193 (2014/01/17)
To cope with developing pest resistance and ecological problems associated with conventional insecticides and to search for potent insecticides targeting at ryanodine receptor (RyR), a series of novel anthranilic diamides containing N-substitued nitrophenylpyrazole were designed and synthesized. The insecticidal activities of target compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) were evaluated in our greenhouse by bio-assay tests and the relative structure-activity relationships were briefly discussed. Most compounds exhibited moderate to high activities, in which G 7 and K5 showed high activity against oriental armyworm and K2 and K4 against diamondback moth even better than the control-chlorantraniliprole. The calcium imaging technique was used to investigate the effects of several typical title compounds on the [Ca 2+]i, especially the effects of G7 on the intracellular calcium ion concentration ([Ca2+]i) in neurons, which indicated that some title compounds were potent activators of the RyR.
Pyrazole-3/5-carboxylic acids from 3/5-trifluoromethyl NH-pyrazoles
Ermolenko, Mikhail S.,Guillou, Sandrine,Janin, Yves L.
, p. 257 - 263 (2013/01/15)
We report here the transformation of 3/5-trifluoromethylpyrazoles derivative into the corresponding NH-pyrazole-3/5-carboxylic acids. Moreover, from 4- or 5-iodinated-3/5-trifluoromethylpyrazoles building blocks and the use of Suzuki-Miyaura or Negishi reactions followed by the trifluoromethyl hydrolysis, we illustrate short and original accesses to many series of NH-pyrazole-3/5-carboxylic acids otherwise difficult to prepare.
A convenient synthesis of 3-polyfluoroalkyl pyrazoles and 6-polyfluoroalkyl pyrimidines from β-polyfluoroalkyl enaminones
Yu, Hong-Bin,Huang, Wei-Yuan
, p. 65 - 67 (2007/10/03)
3-Polyfluoroalkyl pyrazoles and 6-polyfluoroalkyl pyrimidines can be easily synthesized from the reactions of hydrazine monohydrate or amidine respectively with β-polyfluoroalkyl enaminones which are prepared by the nucleophilic substitution of the anion of a methyl ketone with N-aryl polyfluoroalkyl imidoyl iodides.
