120068-79-3Relevant academic research and scientific papers
Design, synthesis, crystal structure and bioactivity evaluation of novel diethyl (arylfuranyl)(arylpyrazolylamino)methanephosphonates
Chen, Fu-li,Wang, Xin-lin,Wang, Zhi-gang,Han, Zhen-yu,Fu, Xiao-huan,Jiang, Peng,Wan, Rong
, p. 1127 - 1133 (2017)
Aseries of novel arylpyrazole derivatives containing aminomethanephosphonate and phenylfuran moieties were designed, synthesized and characterized by 1H NMR, 31P NMR and IR spectroscopy and elemental analyses. The single crystal structure of diethyl [5-(4-chlorophenyl)furan-2-yl][3-cyano-1-(2,3,4-trifluorophenyl)- 1H-pyrazol-5-ylamino]methanephosphonate (4l)was determined by X-ray diffraction. Preliminary bioassays showed that these phosphonates exhibit satisfactory insecticidal activities against Culexpipiens and Musca domestica at 0.1%. In particular, compound 4l exhibited a most promising KT50 value, which is superior to that of Dextraltetramethrin and similar to Prallehtrin. The structure-activity relationship was also preliminarily investigated.
Design, synthesis, crystal structure and insecticidal evaluation of novel arylpyrazole derivatives containing cyhalothroyl thiourea moiety
Han, Zhen-Yu,Wu, Wen-Yuan,Chen, Fu-Li,Guan, Xi-Lin,Fu, Xiao-Huan,Jiang, Peng,Wan, Rong
, p. 911 - 918 (2017)
On the basis of the commercial insecticide Fipronil, a series of novel arylpyrazole derivatives containing the cyhalothroyl thiourea moiety were designed and synthesized via the key intermediate 5-amino-3-cyano-1- (substituted phenyl) pyrazole. The structures of target compoundswere characterized by 1H NMR, FT-IR, elemental analysis and single crystal X-ray diffraction analysis. Their insecticidal activities against Culex pipiens and Musca domesticawere evaluated. The results of bioassays indicated that title compounds exhibited satisfactory insecticidal activities. Among those, Compound 7t ((E)-3-(2-chloro- 3, 3, 3-trifluoroprop-1-en-1-yl)-N- ((3-cyano-1-(2, 6- dichloro-4-(trifluoromethyl) phenyl)-1H-pyrazol-5-yl) carbamothioyl)- 2, 2-dimethyl cyclopropane carboxamide) exhibited the best insecticidal activities because of its lowest KT50 values,which are superior to the commercial insecticide Dextral tetramethrin and similar to Prallethrin. The type and position of substituent on the benzene ring played important roles on the biological activities of target compounds.
Preparation method of 5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethylphenyl)pyrazole
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, (2020/12/30)
The invention provides a preparation method of 5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethylphenyl)pyrazole. The preparation method comprises the following steps of by taking p-trifluoromethylaniline as a raw material, carrying out diazotization reaction to form a ring with ethyl 2, 3-dicyanopropionate under a weakly acidic condition, and introducing a proper amount of chlorine into the cyclization compound for chlorination, and adjusting the pH value for decarboxylation to obtain the product 5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethylphenyl)pyrazole. The preparation method of the5-amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethyl phenyl)pyrazole is simple to operate, good in chlorination selectivity, few in side reaction, high in product yield, mild in reaction condition and beneficial to industrialization; the average yield of the method is not lower than 95%, and the product purity is 99.50% or above.
Method for synthesizing aryl pyrazonitrile and by-producing carbonic acid diester
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Paragraph 0008, (2020/05/01)
The invention discloses a method for synthesizing aryl pyrazonitrile and by-producing carbonic acid diester. The method comprises the steps: taking 2,6-dichloro-4-trifluoromethylaniline, 2,3-dicyanopropionate and nitrite as main raw materials, carrying out diazotization and coupling reaction in a solvent containing fatty alcohol, adding a reaction terminating agent after coupling, and then carrying out alcoholysis and cyclization under an alkaline condition to generate aryl pyrazonitrile and carbonic acid diester. Different raw materials and process conditions are selected, the quality and theyield of the aryl pyrazonitrile are not influenced, and the generated by-product is purposefully controlled, so that after the cyclization liquid for synthesizing aryl pyrazonitrile is distilled andseparated, the distillate is subjected to multi-stage rectification, and solvents (methanol, ethanol or propanol and the like) can be recycled; meanwhile, carbonic acid diester of which the quality meets the industrial standard is obtained, and reduction and resource utilization of aryl pyrazonitrile synthesis waste liquid are realized.
Production method of aryl pyrazole nitrile
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Paragraph 0055-0061, (2020/05/01)
The invention discloses a production method of aryl pyrazole nitrile, which comprises the following steps: dissolving 2, 6-dichloro-4-trifluoromethylaniline and ethyl 2, 3-dicyanopropionate in an acidic solvent to form a solution, adding the solution and sodium nitrite or a suspension composed of sodium nitrite and an alcohol into a reactor at the same time, and reacting to obtain a synthetic solution 1; adding a reducing agent into the synthetic liquid 1 to terminate the reaction to obtain a synthetic liquid 2; adding an alkaline material into the synthetic liquid 2 to carry out alcoholysis and cyclization under an alkaline condition to obtain a synthetic liquid 3; and adding the synthetic liquid 3 into an acidic solvent for neutralization, desolventizing and refining to obtain a target product.
Production method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
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Paragraph 0031-0036, (2020/01/25)
The invention provides a production method of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole. The production method of the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole comprises the following steps: (1) adding nitrosyl sulfuric acid into a four-necked bottle, and adding mixed liquid of 4-amino-3,5-dichlorobenzotrifluoride and an organic solvent dropwise to produce diazonium liquid; (2) adding the diazonium liquid back into ice water, conducting stirring, standing for layering, separating out a water layer, and adding ethyl 2,3-dicyanopropionate dropwise for coupling; and (3) conducting toluene extraction and combining, adding ammonium hydroxide dropwise for cyclization, and conducting filtering, washing and drying to obtain a finished product. According to the production method of the 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, the yield is high, the quality is good, single impurity is lower than or equal to 0.1%, the level ofdifficulty of treating three waste is effectively lowered, discharge of the three waste is reduced, and the cost is low.
Synthesis method of 5-amidogen-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl) pyrazole
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Paragraph 0050; 0054-0056; 0073; 0077-0080; 0081; 0085-0088, (2019/10/01)
The invention discloses a synthesis method of 5-amidogen-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl) pyrazole. The synthesis method comprises the following steps that at 0 to 5 DEG C, an ethanol solution of 2,6-dichloro-4-trifluoromethyl aniline salt and a sodium nitrite solution with the mass concentration being 40 to 45 percent are simultaneously and dropwise added into a hydrochloric acid ethanol solution of 2,3-dicyan ethyl propionate; reaction liquid is subjected to heat insulation for 2 to 12h at 0 to 5 DEG C until the concentration of 2,6-dichloro-4-trifluoromethyl aniline in the reaction liquid is smaller than or equal to 0.5 percent; reducing reagents are dropwise added into the reaction liquid to remove excessive nitrous acid in the reaction liquid until the nitrous acid in the reaction liquid is completely removed; at 10 to 15 DEG C, ammonium hydroxide and ethanol are added into the reaction liquid, so that the pH of the reaction liquid is greater than or equal to 11; heat insulation is performed for 8 to 24h. The synthesis method has the advantages that the technology prejudice of technicians in the field is broken; the cost is reduced; the generation of three wastes is greatly reduced.
Containing chrysanthemic acid structure pyrazole compound and its preparation method and use thereof
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, (2018/11/03)
The invention discloses a pyrazole compound containing chrysanthemic acid structure and a preparation method and purpose of the pyrazole compound with the general structural formula (I). The definition of each substituent group in the general structural formula (I) is showed in the description and claims. The pyrazole compound is good in insect killing effect, simple in production process and high in yield.
Preparation method and application of arylpyrazole compound containing structure of aminophosphonate and aryl furan
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Paragraph 0154-0157, (2018/07/28)
The invention discloses a preparation method and application of an arylpyrazole compound containing a structure of aminophosphonate and aryl furan. The compound has a general molecular formula shown in (I). The compound has a small amount of usage, high insecticide efficiency, a simple process method, low cost and a broad market prospect.
PROCESS FOR PREPARATION OF AMINOPYRAZOLE
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Page/Page column 10; 11, (2017/08/01)
The present disclosure relates to an improved diazotization process for the preparation of 5- amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl) pyrazole.
