A kind of fluorine-containing pyridine piperazine urea compound and its application
A compound and composition technology, applied in the application, organic chemistry, animal repellent and other directions, can solve the problem that the acaricide has not been disclosed, and achieve the effect of avoiding the problem of high drug resistance, small dosage and low toxicity
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example 1
[0018] Example 1, the preparation of intermediate III:
[0019]
[0020] Weigh 17.2g (0.2mol) of anhydrous piperazine into a 250mL reaction flask, add 60mL of methanol, stir to dissolve and raise the temperature to 40°C, then dissolve 21.6g (0.1mol) of 2,3-dichloro-5- (Trifluoromethyl)pyridine was slowly added dropwise into the reaction flask, and after the drop was completed, it was reacted at a constant temperature of 40° C. for 6 h, followed by TLC until the reaction of the raw materials was complete, cooled to room temperature, filtered with suction, and the filtrate was rotary evaporated to remove methanol, and a white solid was precipitated. Add water and stir to dissolve the remaining anhydrous piperazine, filter with suction and wash the filter cake twice to obtain 22.6 g of white solid with a melting point of 65.8-67.3° C. and a yield of 85%.
[0021] 1 H NMR (500MHz, DMSO-d6), δ (ppm) 8.53 (s, 1H), 8.15 (s, 1H), 3.37–3.35 (t, 4H), 2.82–2.80 (t, 4H).
example 2
[0022] Example 2, the preparation of compound I:
[0023]
[0024] Take 5.3g (0.02mol) of intermediate III and add it to a 250mL reaction flask, then add 30g of ethyl acetate, then add 2.22g of triethylamine, and add 1.98g (0.02mol) of n-butyl isocyanate dropwise under stirring. After reacting at 60°C for 40 minutes, TLC traced the complete reaction of intermediate III, added 100mL of water and stirred, separated the liquid, dried the organic phase with anhydrous sodium sulfate, removed ethyl acetate by rotary evaporation, and cooled to obtain 6.8g of white solid, melting point 121.1~122.7 °C, yield 93%.
[0025] 1 H NMR (500MHz, DMSO-d6), δ(ppm): 8.56(s,1H), 8.20(s,1H), 6.54~6.52(t,1H), 3.45~3.39(m,8H), 3.06~3.01 (m,2H),1.42~1.36(m,2H),1.30~1.25(m,2H),0.89~0.85(t,3H).
[0026] Bioactivity assay
example 3
[0027] Example 3, acaricidal activity assay
[0028] Example 3, acaricidal activity assay
[0029] The acaricidal egg activity was determined by dipping method and statistical correction of pest mortality. The specific process is as follows: dilute the test agent to the required concentration according to the active ingredients, draw 50mL of the liquid medicine under aseptic conditions and inject it into the petri dish, and then respectively immerse the cinnabar mite eggs (mite eggs normally raised according to the indoor standardized method) population), and a plate with 50 mL of sterilized water added was used as a blank control. Spirofen was used as a comparative drug. Place the Petri dish in a constant temperature incubator at 24±1°C. After 48 hours, the mortality rate was investigated and counted. Each experiment was repeated 3 times and the average value was taken.
[0030] The acaricidal activity test result of compound I of table 1
[0031]
[0032] According ...
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