Aromatic methylamine compound and its preparation method and anti-plant virus application

A technology of anti-plant virus agent and plant virus disease, which is applied in the field of pesticides, can solve the problems of reducing the severity of symptoms, etc., and achieve the effects of low toxicity, good environmental compatibility, and excellent anti-plant virus activity

Active Publication Date: 2016-10-19
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The development of anti-plant virus agents relies more on extensive screening, and many virus inhibitors can only reduce the severity of symptoms to varying degrees

Method used

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  • Aromatic methylamine compound and its preparation method and anti-plant virus application
  • Aromatic methylamine compound and its preparation method and anti-plant virus application
  • Aromatic methylamine compound and its preparation method and anti-plant virus application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of arylmethylamines 1-3:

[0026]

[0027] Synthesis of 2,3,6,7-Tetramethoxy-9-phenanthrenecarbonyl chloride (67)

[0028] Add 2,3,6,7-tetramethoxy-9-phenanthrenecarboxylic acid (66) 0.80g (2.34mmol), 20mL oxalyl chloride to a 100mL single-neck bottle; add 2 drops of DMF under a water bath; then naturally rise to room temperature, The reaction was continued for another 3 h, and the oxalyl chloride was distilled off at atmospheric pressure to obtain 0.82 g of yellow solid 67; it was directly used in the next reaction without further treatment.

[0029] Synthesis of methyl 2-(N-(2,3,6,7-tetramethoxy-9-phenanthrenyl)amino)acetate (1)

[0030] Add 0.24g glycine methyl ester hydrochloride to 100mL single-neck bottle, 25mL CH 2 Cl 2 , 0.34g Et 3 N, slowly dropwise add 0.40g of 2,3,6,7-tetramethoxy-9-phenanthrenecarbonyl chloride (67) in CH under a water bath 2 Cl 2 The solution was 20 mL. After the dropwise addition, the solution was slowly raise...

Embodiment 2

[0035] Example 2: Synthesis of arylmethylamines 22-26:

[0036]

[0037] Synthesis of 2,3,6,7-Tetramethoxy-9-phenanthrenemethanol (68)

[0038] Add 1.03g of 2,3,6,7-tetramethoxy-9-phenanthrenecarboxylic acid (66) and 20mL of THF to a 100mL single-neck bottle; add 0.28g of LiAlH in batches under ice-water bath cooling 4 , after the addition, heated to reflux for 1.5h, and then cooled to room temperature naturally. 20mL CH was added to the reaction solution 2 Cl 2 , and then slowly add 1 mol / L HCl dropwise to the ice-water bath until the white flocculent precipitate disappears; 2 Cl 2 (10 mL×3) extraction; organic phases were combined, washed once with saturated NaCl solution, anhydrous Na 2 SO 4 dry. Filtration under reduced pressure and concentration to obtain solid were recrystallized from ethyl acetate to obtain white solid, yield 95.0%, melting point: 183-185°C. 1 H NMR (400MHz, CDCl 3 )δ7.83(s, 1H), 7.78(s, 1H), 7.59(s, 1H), 7.55(s, 1H), 7.21(s, 1H), 5.13(s, 2H...

Embodiment 3

[0051] Example 3: Synthesis of arylmethylamines 4-21 and 27-65: (refer to Examples 1 and 2 for the synthesis steps, and the data are as follows)

[0052] Synthesis of methyl 3-(N-(2,3,6,7-tetramethoxy-9-phenanthrenyl)amino)propanoate (4)

[0053] White solid, yield: 90.9%, melting point: 171-172°C. 1 H NMR (400MHz, CDCl 3 )δ7.88(s, 1H), 7.78(s, 1H), 7.74(s, 1H), 7.70(s, 1H), 7.20(s, 1H), 6.75(t, J=5.6Hz, 1H), 4.13(s, 6H), 4.03(s, 6H), 3.86-3.82(m, 2H), 3.73(s, 3H), 2.77(t, J=5.6Hz, 2H); 13 C NMR (100MHz, CDCl 3 )δ173.1, 170.1, 150.2, 149.3, 148.9, 129.9, 125.5, 125.0, 124.7, 124.0, 123.1, 108.6, 106.3, 102.7, 102.5, 56.0, 56.0, 55.9, 55.9, 51.9, 35.5, 34RMS.; (m / z): calcd.forC 23 H 26 NO 7 [M+H] + 428.1704; found428.1707.

[0054] Synthesis of 3-(N-(2,3,6,7-tetramethoxy-9-phenanthrenyl)amino)propionic acid (5)

[0055] White solid, yield: 86.2%, melting point: 222-224°C. 1 H NMR (400MHz, DMSO-d 6 )δ12.27(s, 1H), 8.59(t, J=5.2Hz, 1H), 8.04(s, 1H), 8.01(s, 1H), 7.73(...

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Abstract

The invention relates to an aryl methylamine compound as shown in general formula (I), preparation and application in pesticides. The compound represents a novel and simple antiviral structure type, and the synthetic method is simple, practical, and suitable for industrial amplification. The aryl methylamine compound used as a novel plant virus-resistant agent can well inhibit tobacco mosaic virus, paddy rice virus, capsicum virus, tomato virus, sweet potato virus, potato virus, cucurbit virus and maize dwarf mosaic virus, can effectively control viral diseases of various crops such as tobacco, paddy rice, capsicums, tomatoes, cucurbits and vegetables, grain, vegetables, beans, and the like, and is especially suitable for controlling tobacco mosaic disease. The meanings of Ar, X, R1 and R2 are shown in the description.

Description

technical field [0001] The invention relates to a new type of anti-plant virus agent and its preparation and application, in particular to an arylmethylamine compound as an anti-plant virus agent, which belongs to the technical field of pesticides. Background technique [0002] There are many kinds of plant viruses and their distribution is very wide. In agricultural production, viral diseases are the second largest type of plant diseases after fungi. The vast majority of commercial crops are affected by plant viruses and have reduced yield or quality to varying degrees, and it is extremely difficult to prevent and control them, which is known as "plant cancer". [0003] The development of anti-plant viral agents relies more on extensive screening, and many viral inhibitors can only reduce the severity of symptoms to varying degrees. At present, there are not many effective and satisfactory plant virus inhibitors in practical use, especially the therapeutic agents with spec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/66C07C231/02C07D493/04C07C217/58C07C213/02C07C229/14C07C229/16C07C227/04A01N43/90A01N37/46A01N37/40A01N37/44A01N33/10A01P1/00
Inventor 汪清民王兹稳魏朋刘玉秀王蕾郑彦龙马双王力钟
Owner NANKAI UNIV
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