Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fluorine-containing pyridine piperazine urea compound and application thereof

A technology of pyridine piperazine urea and compounds, which is applied in the field of fluorine-containing pyridine piperazine urea compounds, can solve the problems that acaricides have not been disclosed, and achieve the effects of avoiding high drug resistance, small dosage, and low toxicity

Active Publication Date: 2018-10-12
QINGDAO UNIV OF SCI & TECH
View PDF2 Cites 2 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fluorine-containing pyridine piperazine urea compound and application thereof
  • Fluorine-containing pyridine piperazine urea compound and application thereof
  • Fluorine-containing pyridine piperazine urea compound and application thereof

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 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
melting pointaaaaaaaaaa
Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com