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A kind of glyphosate dicationic ionic liquid compound and its preparation method and application

A double cation and ionic liquid technology, which is applied in botany equipment and methods, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc., can solve the problems of limited cation singleness and improve synthesis efficiency and yield, novel structure, and the effect of promoting absorption and conduction

Active Publication Date: 2021-09-28
ZHEJIANG ACADEMY OF AGRICULTURE SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the introduction of monocations can improve the herbicidal activity to a certain extent, but limited by the singleness of the cations, there is still room for further improvement in the herbicidal activity and herbicidal spectrum of glyphosate monocation-based ionic liquids.

Method used

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  • A kind of glyphosate dicationic ionic liquid compound and its preparation method and application
  • A kind of glyphosate dicationic ionic liquid compound and its preparation method and application
  • A kind of glyphosate dicationic ionic liquid compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of bis(N,N,N,N-tetramethylammonium) glyphosate.

[0021] Add compound N,N,N,N-tetramethylammonium bromide 3.08g (20mmol), methanol 60mL and potassium carbonate 2.76g (20mmol) into a 100mL round bottom flask, react at 25°C for 6 hours, add glyphosate 1.69g (10mmol), stirred and reacted at 65°C for 3 hours. After suction filtration, the filtrate was concentrated to dryness under reduced pressure below 50°C, and then the product was washed with a small amount of dichloromethane, put into a vacuum oven, and dried at 50°C to obtain a white waxy solid with a yield of 95%.

[0022] 1 H NMR (D 2 O, 400MHz), δ3.65(s, 2H), 3.12(s, 24H), 3.04(s, 1H), 3.01(s, 1H); 13 CNMR (D 2 O, 100MHz), δ171.17, 55.21, 50.73, 45.41, 44.36; IRν max [cm -1 ]=3150,1623,1490,1378,1312,1127,949,885,758,550.

Embodiment 2

[0023] Example 2: Preparation of bis(N,N,N-trimethyl-N-hexadecylammonium) glyphosate.

[0024] Add the compound N,N,N-trimethyl-N-hexadecyl ammonium chloride 6.4g (20mmol), acetonitrile 40mL and sodium carbonate 3.18g (30mmol) into a 100mL round bottom flask, and react at 30°C for 3 hours 1.69 g (10 mmol) of glyphosate was added, and the mixture was stirred and reacted at 25° C. for 5 hours. Suction filtration, the filtrate was concentrated to dryness under reduced pressure below 50°C, and then the product was washed with a small amount of dichloromethane, put into a vacuum drying oven, and dried at 50°C to obtain a white waxy solid with a yield of 91%.

[0025] 1 H NMR (D 2 O, 400MHz), δ3.68(s, 1H), 3.32(m, 4H), 3.12(s, 18H), 1.73(s, 4H), 1.30(m, 52H), 0.85(t, J=6.6Hz ,6H); 13 C NMR (D 2 O, 100MHz) δ171.12, 66.46, 52.93, 52.92, 50.68, 45.17, 44.10, 32.05, 30.13, 30.08, 29.95, 29.90, 29.72, 29.60, 29.24, 26.15, 22.77, 22.69, 13.88; IRν max [cm -1 ]=3435,2914,2848,1630,1...

Embodiment 3

[0026] Example 3: Preparation of bis(N,N-dimethyl-N,N-dinonylammonium) glyphosate.

[0027] Add 7.57g (20mmol) of the compound N,N-dimethyl-N,N-dinonylammonium bromide, 20mL of tetrahydrofuran and 0.528g (22mmol) of sodium hydride into a 100mL round bottom flask, and react at 65°C for 1 hour. 1.69 g (10 mmol) of glyphosate was added, and the mixture was stirred and reacted at 30° C. for 1 hour. Suction filtration, the filtrate was concentrated to dryness under reduced pressure below 50°C, and the product was washed with a small amount of dichloromethane, put into a vacuum oven, and dried at 50°C to obtain a pale yellow waxy solid with a yield of 95%.

[0028] 1 H NMR (D 2 O, 400MHz), δ3.69(s, 1H), 3.28(m, 8H), 3.10(s, 12H), 1.65(s, 8H), 1.32(m, 48H), 0.85(t, J=6.6Hz ,12H); 13 C NMR (D 2 O, 100MHz), δ171.18, 61.90, 52.32, 50.82, 49.01, 45.46, 44.12, 32.11, 29.77, 29.55, 29.42, 29.02, 25.88, 22.73, 22.10, 13.87; IRν max [cm -1 ]=3378,2921,2852,1625,1467,1378,1043,904,721,...

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Abstract

The invention relates to a glyphosate dicationic ionic liquid compound and its preparation method and application. Described glyphosate cation-type ionic liquid compound, its structure is as shown in (I): in formula (I): diocation is quaternary ammonium cation, and wherein, R1, R2, R3, R4 are for containing 1-22 The alkyl group of carbon; or the dication is piperidinium cation, wherein, R1, R2 is the alkyl group containing 1-22 carbon; or the dication is a pyridinium cation, wherein R1 is an alkyl group containing 1-22 carbons; or the dication is an imidazolium cation, wherein R1 is a methyl group and R2 is an alkyl group containing 1-9 carbons. The glyphosate dicationic ionic liquid compound of the invention is simple to prepare, has excellent herbicidal activity and wider herbicidal spectrum, and can be used as a herbicide.

Description

technical field [0001] The invention belongs to the field of agricultural herbicides, in particular to a glyphosate dicationic ionic liquid compound and its preparation and application. Background technique [0002] Glyphosate, whose chemical name is: N-(phosphonomethyl) glycine, is an organophosphorus herbicide developed by Monsanto Company of the United States. Glyphosate is a broad-spectrum killing, systemic herbicide, which can be absorbed by the green part of the plant, and it can be absorbed by the stems and leaves and conduct downwards, killing the underground rhizomes of perennial deep-rooted plants; it can also be used in the same Conduct conduction between different tillers of the plant, kill tillers or branches that have not been exposed to the pesticide, and can effectively control almost all annual and perennial grasses, dicotyledonous weeds and shrubs. As the world's largest pesticide, glyphosate herbicide is the most important pesticide to carry out synergist...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/38C07D211/06C07D207/323C07D213/20C07C211/63C07C217/14A01N57/20A01N33/12A01P13/00
CPCA01N33/12A01N57/20C07C211/63C07C217/14C07D207/323C07D211/06C07D213/20C07F9/3813
Inventor 俞建忠许振岚张昌朋陈列忠俞瑞鲜胡秀卿
Owner ZHEJIANG ACADEMY OF AGRICULTURE SCIENCES
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