Method for synthesizing aromatic hydrocarbon/alkane 2,2,2-trifluoroethyl selenium ether through copper catalysis and application of aromatic hydrocarbon/alkane 2,2,2-trifluoroethyl selenium ether to insecticides

A technology for the synthesis of trifluoroethylselenide and aromatic hydrocarbons, which is applied in the fields of pesticides, applications, biocides, etc., can solve the problems of less research on compounds containing 2,2,2-trifluoroethylselenide, and achieve adaptability Good performance, good activity, easy reaction and operation

Active Publication Date: 2019-01-18
FUZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the many compounds containing fluorine groups, there are few studies on compounds containing 2,2,2-trifluoroethylselenide

Method used

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  • Method for synthesizing aromatic hydrocarbon/alkane 2,2,2-trifluoroethyl selenium ether through copper catalysis and application of aromatic hydrocarbon/alkane 2,2,2-trifluoroethyl selenium ether to insecticides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor, then add 0.050 mmol cuprous iodide, 0.050 mmol 1,10-phenanthroline, 0.50 mmol 4-iodobenzoic acid methyl ester, 0.50 mmol of selenium powder, 1.0 mmol of 2,2,2-trifluoroiodoethane, 0.50 mmol of sodium borohydride, and finally 5 mL of N,N-dimethylformamide was added, and the reaction was stirred at 95°C for 16 h in a closed system. Cooled to room temperature, extracted 3 times with dichloromethane, 15 mL each time, combined the organic phases, washed 3 times with distilled water, dried the organic phase with anhydrous magnesium sulfate, filtered, and then rotary evaporated to remove the organic solvent; the obtained crude product was passed through Silica gel column chromatography, eluting with n-pentane, gave methyl 4-(2,2,2-trifluoroethylselenyl)benzoate (isolation yield 68%). 1 H NMR (400 MHz, CDCl 3 ) δ 7.81 (dd, J = 132.4, 7.3 Hz, 4H), 3.94 (s, 3H), 3.46 (q, J = 10.3 Hz, 2H). 19 F NMR ...

Embodiment 2

[0021] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor, then add 0.050 mmol cuprous iodide, 0.050 mmol 1,10-phenanthroline, 0.50 mmol 2-cyanoiodobenzene, 0.50 mmol selenium powder, 1.0 mmol 2,2,2-trifluoroiodoethane, 0.50 mmol sodium borohydride, and finally add 5 mL N,N-dimethylformamide, and stir the reaction at 95°C for 16 h in a closed system, Cooled to room temperature, extracted 3 times with dichloromethane, 15 mL each time, combined the organic phases, washed 3 times with distilled water, dried the organic phase with anhydrous magnesium sulfate, filtered, and then rotary evaporated to remove the organic solvent; the obtained crude product was passed through Silica gel column chromatography, eluting with n-pentane, gave 2-(2,2,2-trifluoroethylselenyl)benzonitrile (98% isolated yield). 1 HNMR (400 MHz, CDCl 3 ) δ 7.83 (d, J = 7.8 Hz, 1H), 7.73 (d, J = 7.6 Hz, 1H),7.56 (t, J = 7.7 Hz, 1H), 7.49 (t, J = 7.6 Hz, 1H), 3.52 (q, J = 10.2 H...

Embodiment 3

[0023] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor, then add 0.050 mmol cuprous iodide, 0.050 mmol 1,10-phenanthroline, 0.50 mmol 1-iodonaphthalene, 0.50 mmol selenium powder, 1.0 mmol 2,2,2-trifluoroiodoethane, 0.50 mmol sodium borohydride, and finally add 5 mL N,N-dimethylformamide, stir and react in a closed system at 95°C for 16 h, then cool to At room temperature, extract 3 times with dichloromethane, 15 mL each time, combine the organic phases, wash 3 times with distilled water, dry the organic phase with anhydrous magnesium sulfate, filter, and then rotary evaporate to remove the organic solvent; the obtained crude product is passed through a silica gel column Chromatography, using n-pentane as the eluent to obtain 1-(2,2,2-trifluoroethyl) naphthalene selenide (isolated yield 91%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.49 (d, J = 8.4 Hz, 1H), 8.03 (d, J = 7.1 Hz, 1H), 7.92(t, 2H), 7.62 (dt, J = 27.4, 7.4 Hz, 2H), 7.44 (t, J = 7.7 Hz, 1H...

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Abstract

The invention relates to the field of crop pest insecticides and particularly relates to a method for synthesizing aromatic hydrocarbon / alkane 2,2,2-trifluoroethyl selenium ether through copper catalysis and application of an aromatic hydrocarbon / alkane 2,2,2-trifluoroethyl selenium ether compound to insecticides. The method comprises the following steps: taking cuprous iodide as a catalyst, taking diimine as a bidentate ligand, taking aromatic hydrocarbon / alkane halogen, selenium powder and 2,2,2-trifluoroiodoethane as reactants, taking sodium borohydride as a reducing agent, stirring for 1-24 hours under 95-110 DEG C in a N,N-dimethylformamide solvent, then carrying out post-treatment on reaction liquid after the reaction is ended to obtain a 2,2,2-trifluoroethyl selenium ether compound.The synthesis method has the advantages that the catalyst is cheap and easily available and is low in toxicity, the raw materials are easily available, the operation is simple and convenient, the functional group universality is high and the like; the fluorine-containing compound has high activity on plutella xylostella, tetranychus cinnabrinus and the like; the death rate of pests under the dosage of 600 mg / L of the fluorine-containing compound reaches up to 100%; the fluorine-containing compound can be used as a novel and efficient fluorine-containing insecticide.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to the field of insecticides for crop pests, in particular to a copper-catalyzed method for synthesizing aromatic hydrocarbons / alkanes 2,2,2-trifluoroethyl selenide and the use of such compounds in insecticides Applications. Background technique [0002] The development of modern agriculture requires the development of new pesticides must have the characteristics of high safety, low residue, pollution-free, high biological activity, high selectivity, and low cost. Fluorine-containing groups have strong electron-withdrawing properties and high lipophilicity, and often exhibit many very unique physical and chemical properties. The introduction of fluorine-containing groups into organic molecules will enhance the lipophilicity of the molecules and promote their absorption and transport in vivo. Among many fluorine-containing compounds, there are few studies on 2,2,2-trifluoroethylseleny...

Claims

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Application Information

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IPC IPC(8): C07C391/02C07D213/24C07D213/61C07D213/65C07D213/85C07D277/66A01N43/40A01N43/78A01N37/34A01N31/14A01P7/02A01P7/04
CPCA01N31/14A01N37/34A01N43/40A01N43/78C07C391/02C07C2603/18C07D213/24C07D213/61C07D213/65C07D213/85C07D277/66
Inventor 翁志强董静楠
Owner FUZHOU UNIVERSITY
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