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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

Active Publication Date: 2020-03-20
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the existing acaricides are carboxylic acid esters and benzamide compounds. The present invention uses piperazine as a bridging chain to connect fluorine-containing pyridine and amide-containing compounds to form a new compound. In the prior art , as described in the present invention, the compound of formula I and its use as acaricide have not been disclosed

Method used

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  • A kind of fluorine-containing pyridine piperazine urea compound and its application
  • A kind of fluorine-containing pyridine piperazine urea compound and its application
  • A kind of fluorine-containing pyridine piperazine urea compound and its application

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention discloses a fluorine-containing pyridine piperazine urea compound. The structure is as shown in the formula I which is as shown in the description. The compound as shown in the formula Ihas effects of restraining and killing pest mites and mite eggs and can be used as an acaricide for controlling agricultural pest mites.

Description

technical field [0001] The invention belongs to the field of acaricides in pesticides, and in particular relates to a fluorine-containing pyridine piperazine urea compound and an application thereof. Background technique [0002] Due to the long-term and frequent use of existing acaricides, mites have developed resistance to them to varying degrees, so the development of new acaricides is an effective way to control the resistance of acaricides. CN102378754A discloses research on the insecticidal and acaricidal activity of 3-aminooxalylaminobenzamide derivatives, and some compounds exhibit high acaricidal activity. CN104285968A discloses the acaricidal activity of an acaricide with tebufenpyrad as an active component, and exhibits excellent acaricidal activity at low concentrations. Most of the existing acaricides are carboxylic acid esters and benzamide compounds. The present invention uses piperazine as a bridging chain to connect fluorine-containing pyridine and amide-co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/75A01N47/38A01P7/02
CPCA01N47/38C07D213/75
Inventor 王明慧彭壮许良忠崔建强
Owner QINGDAO UNIV OF SCI & TECH
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