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

Alpha-amino phosphonate compound with 2-amino-1, 3, 4-thiadiazole structure and preparation method and application of alpha-amino phosphonate compound

An aminophosphonate and thiadiazole technology, applied in the field of pesticides, can solve problems such as undiscovered, and achieve the effects of saving time and cost, good economic benefits, and inhibiting growth and proliferation

Inactive Publication Date: 2016-11-16
GUANGXI TEACHERS EDUCATION UNIV
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no report has been found on the α-aminophosphonate compound of the 2-amino-1,3,4-thiadiazole structure, its preparation method and its use

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
  • Alpha-amino phosphonate compound with 2-amino-1, 3, 4-thiadiazole structure and preparation method and application of alpha-amino phosphonate compound
  • Alpha-amino phosphonate compound with 2-amino-1, 3, 4-thiadiazole structure and preparation method and application of alpha-amino phosphonate compound
  • Alpha-amino phosphonate compound with 2-amino-1, 3, 4-thiadiazole structure and preparation method and application of alpha-amino phosphonate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of O,O'-diethyl-α-(2-amino-1,3,4-thiadiazole)benzyl phosphate:

[0030] Step 1, the preparation of intermediate product

[0031] Weigh 5.00g of thiosemicarbazide, add it to a 50mL three-neck flask with a stirring magnet at one time, add 5.00mL of formic acid, stir and react in an ice bath to form a slurry, and then use a constant pressure dropping funnel to slowly drop 6.00mL concentrated hydrochloric acid. After the dropwise addition, heat in an oil bath at 107°C, and turn on the stirring device, react for 4.5-5.0 hours, follow the reaction by TLC, stop the reaction when the raw material point disappears, and adjust the pH of the system to 8-9 with concentrated ammonia water after cooling at room temperature . Placed in the refrigerator overnight, white crystals precipitated, filtered with suction, washed with ice water three times, and recrystallized with distilled water to obtain 4.96 g of white crystals 1 with a yield of about 90%, m.p.: 198-201°C. Th...

Embodiment 2

[0035] Preparation of O,O'-diethyl-α-(2-amino-1,3,4-thiadiazole)-p-fluorobenzyl phosphate (4):

[0036] Step 1, the preparation of intermediate product

[0037] Add 1.82g (0.02mol) of thiosemicarbazide, 2.54g (0.02mol) of 2-thiophenecarboxylic acid and 20mL of phosphorus oxychloride into the three-necked flask, and slowly raise the temperature to 65°C under magnetic stirring. After 2 hours of reaction, continue to raise the temperature to 106 The reaction was carried out under reflux at ℃ for 4 h, followed by TLC until no raw material was found, and the reaction was stopped. Slowly pour it into ice water while stirring with a glass rod, adjust the pH value to 8-9 with saturated NaOH solution, precipitate out, centrifuge, remove the upper layer, combine the solids, and recrystallize with 75% ethanol to obtain 2.56g of yellow solids 2. Yield: 70%, m.p.: 200-204°C. The structure of the product was determined to be 2-amino-5-thiophene-1,3,4-thiadiazole by IR, NMR and MS analysis...

Embodiment 3

[0041] Preparation of O,O'-diethyl-α-(2-amino-1,3,4-thiadiazole)-o-trifluoromethylbenzyl phosphate:

[0042] Step 1, the preparation of intermediate product

[0043] Add 0.91 g (0.01 mol) of thiosemicarbazide, 2.15 g (0.01 mol) of 2-trifluoromethylbenzoic acid and 20 mL of phosphorus oxychloride into the three-necked flask, and slowly raise the temperature to 65 ° C under magnetic stirring. After 2 hours of reaction, Continue to raise the temperature to 106° C. for reflux reaction for 4 h, TLC traces to the point where there is no raw material, and stop the reaction. Slowly pour it into ice water while stirring with a glass rod, adjust the pH value to 8-9 with saturated NaOH solution, there is precipitation, centrifuge, remove the upper layer, combine the solids, recrystallize with 75% ethanol to obtain 1.99g light green Solid 3, yield 81%, m.p.: 215-221°C. The structure of the product was determined to be 2-amino-5-(trifluoromethyl)phenyl-1,3,4-thiadiazole by IR, NMR and MS...

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 discloses an alpha-amino phosphonate compound with a 2-amino-1, 3, 4-thiadiazole structure and a preparation method and application of alpha-amino phosphonate compound. The alpha-amino phosphonate compound has the sterilizing effect of alpha-amino phosphonate compounds and has a pesticide effect by introducing the 2-amino-1, 3, 4-thiadiazole group, and the alpha-amino phosphonate compound is wide in application range and good in sterilizing and pesticide effect by combining the alpha-amino phosphonate compound with the 2-amino-1, 3, 4-thiadiazole group. The preparation method is few in step, simple to operate, high in yield and productivity, capable of saving a large amount of time and cost in actual production and good in economic benefit. The 2-amino-1, 3, 4-thiadiazole has an inhibition effect on the growth and proliferation of alternaria solani and on the growth of mythimna separata and can be used as the pesticide intermediate to apply to the preparation of different agricultural fungicide.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to an α-aminophosphonate compound having a 2-amino-1,3,4-thiadiazole structure, a preparation method and application thereof. Background technique [0002] In the study of α-aminophosphonate compounds, various synthetic methods have been reported, in which the three components of aldehyde, amine, and phosphite are catalyzed by Lewis acid or Bronsted acid, and synthesized by a "one-pot" method There are many methods for α-aminophosphonate compounds; in 2011, Qiu Jikuan and others reported the synthesis of a new type of α-aminophosphonate derivatives containing pyrazolyl groups; The synthesis of phosphonate derivatives, in 2013, Abdel-Rahman et al. reported that by adding boron trifluoride to the three components of p-fluoroaniline, monoaldehyde (or dialdehyde) and diethyl phosphite , carried out a "one-pot cooking" reaction, and synthesized a series of new fluorinated α-aminophos...

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
IPC IPC(8): C07F9/6539C07F9/6558A01N57/24A01P1/00A01P3/00A01P7/04
CPCA01N57/24C07F9/65395C07F9/6558
Inventor 黄燕敏何冬梅崔建国莫宇星卢瑞甘春芳莫平玲
Owner GUANGXI TEACHERS EDUCATION 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