141573-95-7Relevant articles and documents
Crystal structure and molecular docking studies of new pyrazole-4-carboxamides
Qiao, Li,Cai, Peng-Peng,Shen, Zhong-Hua,Wu, Hong-Ke,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
, p. 66 - 72 (2019)
Two pyrazol-4-carboxamides, 3-(difluoromethyl)-N-(mesitylcarbamoyl)-1-methyl-1H-pyrazole-4-carboxa-mide (7a) and 3-(difluoromethyl)-N-((3,5-dimethylphenyl) carbamoyl)-1-methyl-1H-pyrazole-4-carboxamide (7b) were synthesized and their structures were confirmed by the aid of 1H NMR and HRMS analyses. The structure of the pyrazole-4-carboxamide, 7a was also determined by X-ray diffraction. The preliminary activity results demonstrate that these two compounds exhibit good inhibitory activity against Botrytis cinerea. Further docking results indicated that the key active group is difluoromethyl pyrazole moiety.
Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties
Liu, Xing-Hai,Zhao, Wen,Shen, Zhong-Hua,Xing, Jia-Hua,Xu, Tian-Ming,Peng, Wei-Li
, p. 881 - 889 (2017)
A series of novel difluoromethylpyrazole carboxamides derivatives were synthesized by introduction of flexible alkyl chain. Nematicidal bioassay results showed that some of them exhibited good control efficacy against M. incognita, which indicated that these difluoromethylpyrazole carboxamides derivatives might be potential novel lead compounds for discovery new nematicides. The nematicidal activity was affected by the substituted position in the molecule, especially the substitution group on the alkyl chain. It was found that the compound 6-9 and 6-23 possess about 50% inhibition effect against M. incognita even at 5.0 and 1.0 mg L?1. Meanwhile, greenhouse field trial showed the nematicidal activity of compound 6-9 is a litter weaker than that of Abamectin. The mammalian toxicology results indicated that compound 6-9 was a low-toxicity and low-sensitive compound. In conclusion compound 6-9 is a potential candidate for further development. In addition, the molecular docking simulations revealed that compounds 6 with a flexible NHCOO show its binding affinities for the acetylcholine receptor (AChR), which may provide useful information for further design novel nematicides.
Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives
Qiao, Li,Zhai, Zhi-Wen,Cai, Peng-Peng,Tan, Cheng-Xia,Weng, Jian-Quan,Han, Liang,Liu, Xing-Hai,Zhang, Yong-Gang
, p. 2536 - 2541 (2019)
Nine novel difluoromethylpyrazole acyl urea derivatives were synthesized via seven steps conveniently. All the structures were determined by 1H-NMR, 13C-NMR, HRMS, and X-ray diffraction. The in vivo fungicidal activities were determined against Corynespora mazei, Botrytis cinerea, Fusarium oxysporum, and Pseudomonas syringae, respectively. The bioassay results indicated that some of them displayed good control effective (around 50 and 80%) against P. syringae and B. cinerea at 50 mg/L, respectively, which is better than control. It is possible that difluoromethylpyrazole acyl urea derivatives can be a leading compound for the development of new fungicides against the two fungi with further structure optimization. Furthermore, docking model was studied to establish structure–activity relationship of difluoromethylpyrazole acyl urea derivatives.
Synthesis and preparation method of 4-pyrazole ethyl formate
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, (2021/03/13)
The invention discloses a synthesis and preparation method of 4-pyrazole ethyl formate. The method comprises the following steps: dissolving ethyl 2-dichloroacetyl-3-(dimethylamino) acrylate in an organic solvent, and reacting with methylhydrazine to obtain ethyl 1-methyl-3-dichloromethyl-4-pyrazole formate; reacting the obtained ethyl 1-methyl-3-dichloromethyl-4-pyrazole formate with a fluorination reagent to obtain 1-methyl- 3-difluoromethyl-4-pyrazole ethyl formate; mixing 1-methyl- 3-difluoromethyl-4-pyrazole ethyl formate with glacial acetic acid, dropwise adding a strong acidic solutionat the temperature of 0 DEG C, and then adding dichloromethane and water for stirring and layering to obtain an organic layer; and recrystallizing the organic layer by using a mixed solvent of petroleum ether and ethyl acetate to obtain the 4-pyrazole ethyl formate. The method has the advantages of wide raw material source, low raw material price and simple preparation process, and the obtained product is easy to purify, low in production cost and suitable for large-scale industrial production.
Preparation method for polyhalogenated methylpyrazole formate
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Paragraph 0036-0065, (2020/05/02)
The invention discloses a preparation method for polyhalogenated methylpyrazole formate. The preparation method comprises the following specific steps: with a compound with a chemical structural formula I which is described in the specification and formyl acetate sodium salt as raw materials, subjecting the compound and the formyl acetate sodium salt to a low-temperature reaction in an organic solvent for 0.5-4 h under the action of a quaternary ammonium salt catalyst, then adding substituted hydrazine, and carrying out a cyclization reaction for 0.5-4 h so as to generate the polyhalogenated methylpyrazole formate as shown in a formula II which is described in the specification. The preparation method provided by the invention has the advantages of safe and easily-controllable process, mild synthesis condition, high atom economy, low emission of three wastes and good industrial value.
