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

Trifluoromethyl-containing pyrimidinamine compound, preparation method thereof, and application of trifluoromethyl-containing pyrimidinamine compound used as bacteriacide

A technology of trifluoromethylpyrimidine ammonia compound and synthesis method, which is applied in the field of agricultural chemicals to achieve good bactericidal effect

Inactive Publication Date: 2012-08-01
SHENYANG AGRI UNIV
View PDF4 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the synthesis and fungicidal activity of trifluoromethylpyrimidine-containing compounds

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
  • Trifluoromethyl-containing pyrimidinamine compound, preparation method thereof, and application of trifluoromethyl-containing pyrimidinamine compound used as bacteriacide
  • Trifluoromethyl-containing pyrimidinamine compound, preparation method thereof, and application of trifluoromethyl-containing pyrimidinamine compound used as bacteriacide
  • Trifluoromethyl-containing pyrimidinamine compound, preparation method thereof, and application of trifluoromethyl-containing pyrimidinamine compound used as bacteriacide

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0017] Synthesis of Example 1.4-(2-fluorophenyl)-6-trifluoromethyl-2-aminopyrimidine (III-1)

[0018] Add 30 mL of methanol into a single-necked bottle, cut 0.2 mol of sodium metal into chips at 0-5°C, and add small amounts of it several times to prepare a sodium methoxide solution for later use. Add 60 mL of methanol, 0.1 mol of 2-fluoroacetophenone, and 0.15 mol of ethyl trifluoroacetate into the three-necked flask and stir evenly, then slowly add sodium methoxide dropwise into the three-necked flask, and control the temperature of the reaction solution at 30°C during the dropping process the following. After the dropwise addition, the temperature was raised to reflux for 1 h. The reaction solution was left to cool to room temperature, 50 mL of methanol was evaporated under reduced pressure, poured into 100 mL of ice water containing 30 mL of hydrochloric acid, stirred with a glass rod, a large amount of yellow solids precipitated, suction filtered, washed with water, and d...

example 2

[0028] Example 2. Preliminary screening of the bactericidal activity of compounds III-1~III-15

[0029] The mycelial growth rate method was used to measure the bactericidal activity of the target compound at 50 mg / L to the tested pathogenic fungi. Use a puncher with a diameter of 6 mm to make bacterial blocks from each pathogenic bacteria grown on the PDA medium, inoculate it on the poisonous PDA medium, cultivate it at 23°C±1°C for 3-5 days, and measure the colony by the cross method Diameter, according to (1) to calculate the inhibition rate.

[0030] Inhibition rate (%)=(blank control colony diameter-toxic medium colony diameter) / (blank control colony diameter-bacteria cake diameter)×100(1)

[0031] The bactericidal activity of the compound against 8 kinds of pathogenic bacteria was tested, and the test results are shown in Table 3. At a concentration of 50 μg / mL, compounds III-1, III-2, III-5, III-6, and III-10 showed high inhibitory activity against multiple pathogenic ...

example 3

[0034] Example 3. Compounds III-1~III-15 are tested for precision toxicity of Botrytis cinerea

[0035] The toxicity of 15 new compounds to Botrytis cinerea was measured by mycelium growth rate method, and the test results are shown in Table 4. The sample compounds were respectively configured into toxic media with concentrations of 100, 25, 6.25, 1.56, and 0.39 mg / L, a total of five gradients. Use cyprodinil as the control agent, set acetone as the blank control, and repeat three times. Using the statistical method of EXCEL software to calculate EC 50 , EC 80 value, to compare the toxicity of medicines.

[0036] EC from Table 3 50 and EC 80 It can be seen from the data that the toxicity of compounds III-1, III-10 and III-13 to Botrytis cinerea is higher than that of the control drug cyprodinil, especially the bactericidal activity of III-10 is significantly higher than that of other compounds.

[0037] Table 4 Compound III-1~III-15 is to the toxicity determination of Bo...

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

No PUM Login to View More

Abstract

The invention relates to a 4-substituted phenyl-6-trifluoromethyl-2-amino pyrimidinamine compound which has a novel chemical structure and a general formula III, a synthesis method for the compound and the application of the compound used as bacteriacide. The method comprises the following steps of: reacting substituted phenyl methyl ketone used as an initial raw material and trifluoroacetic acid ethyl ester under catalysis of sodium alcoholate to generate 4,4,4-trifluoro-1-substituded phenylbutane-1,3-diketone, and reacting 4,4,4-trifluoro-1-substituded phenylbutane-1,3-diketone and guanidinium salt under an alkaline condition to generate a III series compound with the general formula III. The compound with the general formula III can inhibit growth of pathogenic bacteria such as rice sheath blight, rice bakanae disease, exserohilum turcicum, bipolaris maydis, curvulavia lunata, corn kernel rot, corn top rot pathogenic bacteria, fusarium graminearum, cotton anthracnose, bean fusarium, rape sclerotinia rot, botrytis cinerea, cucumber fusarium wilt pathogenic bacteria, cucumber brown rot pathogenic bacteria, cucumber scab pathogenic bacteria, hot pepper root rot pathogenic bacteria, kidney bean anthracnose bacteria, and pythium aphanidermatum. In the formula III, R is methyl, ethyl, methoxy group, fluorine, chlorine, bromine, trifluoromethyl and other groups, and the number of R is 1 to 3.

Description

technical field [0001] The invention relates to an agricultural chemical, especially a 4-substituted phenyl-6-trifluoromethyl-2-aminopyrimidine compound, a synthesis method and use as a fungicide. Background technique [0002] Pyrimidine amine compounds are a class of fungicides with a unique mechanism of action. This type of agent has a weak antibacterial effect on pathogens in vitro, but it shows a good control effect on host plants. The main mechanism is to inhibit the decomposition of the cell wall of pathogens. Enzyme secretion and interference with methionine biosynthesis. No cross-resistance with triazoles, imidazoles, morpholines, dicarboximides, phenylpyrroles, etc. The main species used in production now are pyrimethanil (pyrimethanil, 1992, now Bayer), which is mainly used to prevent gray mold, and the resistance of bacteria to it has developed rapidly in recent years; , Japan Combination Chemical Company), mainly used in the prevention and treatment of Botrytis...

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): C07D239/42A01N43/54A01P3/00
Inventor 李兴海纪明山祁之秋谷祖敏张杨魏松红王英姿李修伟
Owner SHENYANG AGRI UNIV
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