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Application of alkaloid essramycin and its derivatives in anti-plant virus

An anti-plant virus and anti-plant virus agent technology, applied in the direction of chemicals, applications, and plant growth regulators for biological control, can solve the problems of poor stability and solubility, low synthesis yield, etc., and achieve expanded application Range, good effect on anti-plant virus activity

Active Publication Date: 2021-05-18
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the synthetic method of alkaloid essramycin reported, the synthetic yield of important intermediate 2-(5-amino-1H-1,2,4-triazol-3-yl)-1-phenylethan-1-one is relatively Low, mainly by-products, and has disadvantages such as poor stability and solubility

Method used

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  • Application of alkaloid essramycin and its derivatives in anti-plant virus
  • Application of alkaloid essramycin and its derivatives in anti-plant virus
  • Application of alkaloid essramycin and its derivatives in anti-plant virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation method of essramycin shown in chemical structural formula Ia-1 is as follows:

[0023] The chemical structural formula Ia-1 of Essramycin is

[0024]

[0025] The concrete steps of its preparation method are as follows:

[0026] The first step, in the there-necked flask of 250mL, add aminoguanidine bicarbonate (9.64g, 0.07mol), ethyl benzoyl acetate (13.44g, 0.07mol) and n-butanol (40mL) and carry out heating and reflux reaction temperature control at Reflux at 130°C for 3 hours. After the reaction, cool the system to room temperature to precipitate a large amount of light brown solid. After suction filtration and drying, add 50 mL of DMF to the obtained solid product and stir. Stir for more than 30 minutes, and then carry out suction filtration. After washing with DMF and washing with water, the compound 2-(5-amino-1H-1,2,4-triazol-3-yl)-1-phenylethan-1-one was obtained as a white solid, yield 6%, melting point 198°C - 202°C; 1 HNMR (DMSO-d 6 ,40...

Embodiment 2

[0029] 2-(5-methyl-7-oxo-4,7-dihydro-[1,2,4]triazol[1,5-a]pyrimidin-2-yl)acetic acid shown in chemical structure Ia-2 The preparation method is as follows:

[0030] The chemical formula Ia-2 of 2-(5-methyl-7-oxo-4,7-dihydro-[1,2,4]triazol[1,5-a]pyrimidin-2-yl)acetic acid is

[0031]

[0032] The concrete steps of its preparation method are as follows:

[0033] Except replacing 2-(5-amino-1H-1,2,4-triazol-3-yl)-1 with 2-(5-amino-1H-1,2,4-triazol-3-yl)acetic acid -Except for phenylethan-1-one, the others are the same as the second step of Example 1, a white solid with a yield of 97% and a melting point of 257-259°C; 1 H NMR (DMSO-d 6 ,400MHz):12.90(br s,2H,NH),5.82(s,1H,C=CH),3.73(s,2H,CH 2 ),2.32(s,3H,CH 3 ); 13 C NMR (DMSO-d 6 ,100MHz):170.7,159.2,156.0,151.8,151.3,98.7,35.4,19.1; HR-MS(ESI):Calcd for C 8 h 9 N 4 o 3 [M+H] + 209.0669, found (ESI + ) 209.0672, the product was determined to be 2-(5-methyl-7-oxo-4,7-dihydro-[1,2,4]triazol[1,5-a]pyrimidin-2-yl)acet...

Embodiment 3

[0035] The preparation method of 5-methyl-7-oxo-4,7-dihydro-[1,2,4]triazol[1,5-a]pyrimidine-2-carboxylic acid methyl ester shown in chemical structural formula Ia-3 as follows:

[0036] The chemical structure Ia-3 of methyl 5-methyl-7-oxo-4,7-dihydro-[1,2,4]triazol[1,5-a]pyrimidine-2-carboxylate is

[0037]

[0038] The concrete steps of its preparation method are as follows:

[0039] Except replacing 2-(5-amino-1H-1,2,4-triazol-3-yl)-1-phenyl with methyl 5-amino-1H-1,2,4-triazole-3-carboxylate Except for ethyl-1-one, the others are the same as the second step of Example 1, white solid with a yield of 98% and a melting point of 232-234°C; 1 HNMR (DMSO-d 6 ,400MHz):13.39(br s,1H,NH),5.94(s,1H,C=CH),3.91(s,3H,OCH 3 ),2.35(s,3H,CCH 3 ); 13 C NMR (DMSO-d 6 ,100MHz):160.0,155.6,153.0,152.7,151.1,98.7,52.6,18.8; HR-MS(ESI):Calcd for C 8 h 9 N 4 o 3 [M+H] + 209.0669, found (ESI + ) 209.0668, the product was determined to be methyl 5-methyl-7-oxo-4,7-dihydro-[1,2,4]tri...

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Abstract

The present invention is the application of the alkaloid essramycin and its derivatives in anti-plant virus, the chemical structural formula of the alkaloid essramycin is as follows, specifically the alkaloid essramycin and its derivatives are used as an anti-plant virus agent, the The anti-plant virus agent is used for tobacco mosaic virus, pepper virus, rice virus, tomato virus, sweet potato virus, potato virus, melon virus and corn dwarf mosaic virus.

Description

technical field [0001] The invention relates to the application of alkaloid essramycin and its derivatives in anti-plant virus, belonging to the technical field of agricultural protection. Background technique [0002] The marine microbial resources in the ocean are very rich. Due to the unique living environment of high salinity, lack of nutrition and high pressure, marine microorganisms can produce natural active substances with novel structures and unique functions. Past research has strongly proved this point, and the separation has been Many active metabolites, many of which are marine microbial metabolites have the effects of killing insects, weeds, and resisting bacteria (Insect Knowledge, 2004, 5, 409–413). Choosing marine natural products as the object of natural source pesticide development not only brings into play the advantages of natural source pesticide resources, good environmental compatibility, and human and animal safety, but also combines the characterist...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/90A01P1/00C07D487/04
CPCA01N43/90C07D487/04
Inventor 卢爱党田兆永李红岩王铁男汪清民
Owner HEBEI UNIV OF TECH
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