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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, no report has been found on the α-aminophosphonate compound o...

Method used

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  • 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
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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...

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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

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Application Information

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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
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