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Chiral primary amine malonamide compound as well as preparation method and application thereof

A primary amine malonamide and compound technology, applied in the field of chiral primary amine malonamide compounds and their preparation, can solve the problems of low field control effect, few practical varieties, environmental risks and the like, and achieve good resistance to tobacco flowers. Effect of Leaf Virus Activity

Active Publication Date: 2022-02-15
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many types of anti-plant virus agents, such as benzothiadiazole (BTH), thiazilamide (TDL), 4-methyl-1,2,3-thiadiazole-5-carboxylic acid (TDLA), DL-β-aminobutyric acid (BABA), ribavirin, ningnanmycin, phenanthroindolidine alkaloid antorfen, virus A, salicylic acid, amino oligosaccharins, etc., but these anti-plant There are not many practical varieties of virus agents, and the field control effect is generally lower than 60%. There are certain environmental risks in long-term use

Method used

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  • Chiral primary amine malonamide compound as well as preparation method and application thereof
  • Chiral primary amine malonamide compound as well as preparation method and application thereof
  • Chiral primary amine malonamide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] N shown in chemical structural formula I-1 1 -((1R,2R)-2-amino-1,2-diphenylethyl)-N 3 -The preparation method of phenylmalonamide is as reaction formula one:

[0026]

[0027] N 1 -((1R,2R)-2-amino-1,2-diphenylethyl)-N 3 -The chemical structural formula I-1 of phenylmalonamide is

[0028]

[0029] The concrete steps of its preparation method are as follows:

[0030] In the first step, 3-oxo-3-(phenylamino)propionic acid (1.79g, 10mmol), (1R,2R)-N-tert-butoxycarbonyl-1,2-diphenylethylenediamine ( 3.12g, 10mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (2.30g, 12mmol), diisopropylethylamine (DIPEA, 2.58g, 20mmol) 1-Hydroxybenzotriazole (HOBt, 1.62g, 12mmol) was added to 50mL THF, stirred at room temperature at 25°C for 8 hours, after the reaction was completed, the solvent was removed in vacuo, and the residual liquid was dissolved in 30mL dichloromethane and saturated saline After washing, the organic phase was dried to obtain the crude pro...

Embodiment 2

[0033] N shown in chemical structural formula I-2 1 -((1R,2R)-2-amino-1,2-diphenylethyl)-N 3 The preparation method of -(4-fluorophenyl) malonamide is as follows:

[0034] N 1 -((1R,2R)-2-amino-1,2-diphenylethyl)-N 3 The chemical structural formula I-2 of -(4-fluorophenyl) malonamide is

[0035]

[0036] The concrete steps of its preparation method are as follows:

[0037] In the first step, except that 3-((4-fluorophenyl)amino)-3-oxopropionic acid is used to replace 3-oxo-3-(phenylamino)propionic acid, other experimental steps are the same as in Example 1, Go to the next step directly without purification;

[0038] In the second step, the crude product obtained in the previous step is processed according to the experimental procedure of Example 1 to obtain a light yellow solid with a yield of 96%; after determination, the relevant parameters of the light yellow solid are: 1 H NMR (400MHz, CDCl 3 )δ9.47(s,1H),8.05(s,1H),7.42(dd,J=8.8,4.9Hz,2H),7.29(m,7.9Hz,11H),7.18(...

Embodiment 3

[0040] N shown in chemical structural formula I-3 1 -((1R,2R)-2-amino-1,2-diphenylethyl)-N 3 The preparation method of -(2-chlorophenyl) malonamide is as follows:

[0041] N 1 -((1R,2R)-2-amino-1,2-diphenylethyl)-N 3 The chemical structural formula I-3 of -(2-chlorophenyl) malonamide is

[0042]

[0043] The concrete steps of its preparation method are as follows:

[0044] In the first step, except that 3-((2-chlorophenyl)amino)-3-oxopropionic acid is used to replace 3-oxo-3-(phenylamino)propionic acid, other experimental steps are the same as in Example 1, Go to the next step directly without purification;

[0045] In the second step, the crude product obtained in the previous step was processed according to the experimental procedure of Example 1 to obtain a light yellow solid with a yield of 87%; after determination, the relevant parameters of the light yellow solid were: 1 H NMR (400MHz, CDCl 3 )δ9.48(s,1H),8.33(dd,J=8.2,1.5Hz,1H),7.54(d,J=8.3Hz,1H),7.42–7.30(m,8...

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Abstract

The invention relates to a chiral primary amine malonamide compound as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification. In the preparation method, (1R,2R)-1,2-diphenylethylenediamine reacts with a malonic acid derivative to obtain the chiral primary amine malonamide compound containing a malonamide structural unit. The chiral primary amine malonamide compound obtained by the preparation method disclosed by the invention has very good tobacco mosaic virus resisting activity.

Description

technical field [0001] The technical scheme of the present invention relates to the anti-tobacco mosaic virus agent related to chiral primary amine malonamide compounds, specifically containing (1R,2R)-1,2-diphenylethylenediamine skeleton and containing malonamide Chiral primary amine malonamide compound of structure and its preparation method and use. Background technique [0002] Plant viruses are widely distributed in nature. They cause serious damage to the growth of crops, and then cause great losses to modern agricultural production. Tobacco mosaic virus (TMV), as a pathogen, can cause harm to many crops. According to statistics, it can infect about 198 kinds of individuals of 22 kinds of monocotyledonous plants, and can cause losses ranging from about 5% to 90% (Hari, V.; Das, P. Ultra microscopic detection of plant viruses and their gene products. In plant disease virus control. Hadidi, A.; Khetarpal, R.K.; Koganezawa, H., Eds.; APS Press: St.Paul, MN, 1998:417-427....

Claims

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Application Information

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IPC IPC(8): C07C233/36C07C231/12C07C269/06C07C271/20A01N37/30A01P1/00
CPCC07C233/36C07C231/12C07C269/06A01N37/30C07B2200/07C07C271/20Y02P20/55
Inventor 卢爱党王佳莉田兆永王铁男李红岩
Owner HEBEI UNIV OF TECH
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