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Biphenyl alpha-aminophosphonate compound as well as preparation method and application thereof

A technology of amino phosphonate and methyl phosphonate, applied in the field of drug synthesis, can solve problems such as unsatisfactory control effects, and achieve the effects of mild reaction conditions, easy availability of raw materials, and simple operation of the reaction process

Inactive Publication Date: 2015-07-29
张国平
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these measures are still difficult to effectively implement in actual production, and the use of chemical agents to prevent and control plant virus diseases is an economical and effective measure.
At present, there are commercially available agents such as Virusbigram, Virus A, Ningnanmycin, Dufluphosphine, etc., but the control effects of these agents are still not ideal (mostly 30-60%)

Method used

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  • Biphenyl alpha-aminophosphonate compound as well as preparation method and application thereof
  • Biphenyl alpha-aminophosphonate compound as well as preparation method and application thereof
  • Biphenyl alpha-aminophosphonate compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Compound O, the synthesis of O'-diethyl-1-(phenylamino)-1-(4-biphenyl)methylphosphonate (4a):

[0046] (1) Synthesis of 4-biphenyl formaldehyde:

[0047] Add potassium carbonate (0.212g, 3mmol), palladium acetate (2mg, 0.03mmol), polyethanol 2000 (3.5g) and water (3mL) into a 25mL round bottom flask, heat the system to 50°C and stir well, then add p-Aldehydophenylboronic acid (0.225g, 1.5mmol) and iodobenzene (0.204g, 1mmol) were placed in a reaction flask, under the protection of nitrogen, the reaction was carried out for 12h, cooled to room temperature after the reaction, the reaction product was filtered with toluene (3 × 10mL) to extract the filtrate, the extracted organic phase was washed and dried, and the solvent was evaporated, and the white solid biphenyl formaldehyde was obtained by recrystallization from petroleum ether, with a yield of 93% and a melting point of 54-55°C;

[0048] (2) Compound O, the synthesis of O'-diethyl-1-(phenylamino)-1-(4-biphenyl)meth...

Embodiment 2

[0051] Compound O, O'-diethyl-1-(phenylamino)-1-(4'-methoxy-4-biphenyl)methylphosphonate (4b)

[0052] (1) Synthesis of 4'-methoxyl 4-biphenyl formaldehyde:

[0053] The synthesis method and conditions are the same as those in Example 1(1). The difference is that 4-methoxyiodobenzene (234mg, 1.0mmol) was added, the reaction time was 12h, the yield was 96%, and the melting point was 102-103°C.

[0054] (2) Compound O, the synthesis of O'-diethyl-1-(phenylamino)-1-(4'-methoxy-4-biphenyl)methylphosphonate:

[0055] The synthesis method and conditions are the same as those in Example 1(2). The difference is that 4'-methoxy 4-biphenylcarbaldehyde (106mg, 0.5mmol) was added, the reaction time was 6h, the yield was 83%, and the melting point was 101-103°C.

Embodiment 3

[0057] Compound O, O'-diethyl-1-(4-methylanilino)-1-(4'-methoxy-4-biphenyl)methylphosphonate (4c)

[0058] (1) Synthesis of 4'-methoxyl 4-biphenyl formaldehyde:

[0059] The synthesis method and conditions are the same as those in Example 2(1).

[0060] (2) Compound O, the synthesis of O'-diethyl-1-(4-methylanilino)-1-(4'-methoxy-4-biphenyl)methylphosphonate:

[0061] The synthesis method and conditions are the same as those in Example 2(2). The difference is that 4-methylaniline (54mg, 0.5mmol) was added, the reaction time was 6h, the yield was 86%, and the melting point was 151-153°C.

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Abstract

The invention discloses a biphenyl alpha-aminophosphonate compound as well as a preparation method and an application thereof. The structural formula of the compound is shown in the specification. The compound has very good antiviral activity on plant viruses and can be applied to preparation of anti-plant-virus pesticides, especially anti-CMV (cucumber mosaic virus) pesticides. The preparation method of the biphenyl alpha-aminophosphonate compound has the advantages that raw materials are easy to obtain, reaction conditions are mild, a reaction process is simple to operate, a reagent is cheap and the like.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method and application of biphenyl α-aminophosphonate compounds with anti-plant virus effects. Background technique [0002] Plant virus diseases have the characteristics of wide distribution, serious harm, and difficulty in prevention and control, so they are also called "plant cancer". Common plant viruses include tobacco mosaic virus TMV, cucumber mosaic virus CMV, alfalfa mosaic virus AMV, and southern rice black-streaked dwarf virus SRBSDV. Due to the absolute parasitic and systemic infectivity of plant viruses, once plants are infected with viruses, it will be difficult to control their spread. In addition, plant viruses have a wide range of hazards. Only CMV can harm more than 1,000 crops. Almost every crop and economic crop may be harmed by more than two viruses. This makes the prevention and control of plant viruses a major problem in agricultural...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/6539C07F9/6541A01P1/00
Inventor 张国平
Owner 张国平
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