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Aryl methylamine compound and preparation method thereof and application in resisting plant virus

An anti-plant virus agent, arylmethylamine technology, applied in the field of pesticides, can solve problems such as reducing the severity of symptoms, and achieve the effects of low toxicity, significant anti-plant virus activity, and stable chemical properties

Active Publication Date: 2015-03-18
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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  • Aryl methylamine compound and preparation method thereof and application in resisting plant virus
  • Aryl methylamine compound and preparation method thereof and application in resisting plant virus
  • Aryl methylamine compound and preparation method thereof and application in resisting plant virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: the synthesis of aromatic methylamine 1-3:

[0026]

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

[0028] Add 0.80g (2.34mmol) of 2,3,6,7-tetramethoxy-9-phenanthrene acid (66) and 20mL oxalyl chloride into a 100mL single-necked bottle; add 2 drops of DMF in a water bath; then naturally rise to room temperature, After reacting for another 3 h, the oxalyl chloride was evaporated under normal 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-phenanthrene)amino)acetate (1)

[0030] Add 0.24g glycine methyl ester hydrochloride, 25mL CH 2 Cl 2 , 0.34g Et 3 N, slowly dropwise add 0.40g of 2,3,6,7-tetramethoxy-9-phenanthroyl chloride (67) in CH 2 Cl 2 The solution was 20 mL, and after the dropwise addition was completed, it was slowly raised to room temperature and reacted for 2 hours, and TLC detected that ...

Embodiment 2

[0035] Embodiment 2: the synthesis of aromatic methylamine 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-phenanthroic acid (66) and 20mL THF into a 100mL single-necked bottle; add 0.28g of LiAlH in batches under cooling in an ice-water bath 4 , After the addition is complete, heat to reflux for 1.5h, then cool naturally to room temperature. Add 20 mL of CH to the reaction solution 2 Cl 2 , and then slowly add 1mol / L HCl dropwise in an ice-water bath until the white flocculent precipitate disappears; 2 Cl 2 (10mL×3) extraction; combined organic phase, washed once with saturated NaCl solution, anhydrous NaCl 2 SO 4 dry. Filtrate under reduced pressure and then concentrate to obtain a solid, which is then recrystallized with ethyl acetate to obtain a white solid with a yield of 95.0% and a melting point of 183-185°C. 1 H NMR (400MHz, CDCl 3 )δ7.83(s, 1H), 7.78(s, 1H), 7.59(s, 1H), 7....

Embodiment 3

[0051] Embodiment 3: the synthesis of arylmethylamine 4-21 and 27-65: (synthetic steps are with reference to embodiment 1 and 2, data are as follows)

[0052] Synthesis of methyl 3-(N-(2,3,6,7-tetramethoxy-9-phenanthroyl)amino)propionate (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, 35.9, 34. (m / z): calcd.for C 23 h 26 NO 7 [M+H] + 428.1704; found 428.1707.

[0054] Synthesis of 3-(N-(2,3,6,7-tetramethoxy-9-phenanthroyl)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 novel anti-plant virus agent and its preparation and application, in particular to aromatic methylamine compounds as anti-plant virus agents, and 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, virus diseases are the second largest type of plant diseases after fungi. The vast majority of economic crops are affected by plant viruses, resulting in varying degrees of yield reduction or quality degradation, which is extremely difficult to control and is known as "plant cancer". [0003] The development of anti-plant virus agents relies more on a large number of screenings, and many virus inhibitors can only reduce the severity of symptoms to varying degrees. At present, there are not many practical varieties of effective and satisfactory plant virus inhibitors, and especially the therapeutic agents w...

Claims

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Application Information

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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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