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Aromatic amine schiff base derivative of gossypol and preparation method and plant-virus resisting application thereof

A technology of aromatic amine Schiff base and anti-plant virus agent, which is applied in the field of pesticides, can solve the problems of reducing the severity of symptoms, not many, etc., and achieve the effects of low toxicity, easy preparation, and significant anti-plant virus activity

Active Publication Date: 2015-09-16
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, antiviral agents are mainly used in the prevention and treatment of plant virus diseases. Many virus inhibitors can only reduce the severity of symptoms. At present, there are not many effective and satisfactory plant virus inhibitors in practical use, especially less effective therapeutic agents. , when the reported medicament is actually applied in the field, its control effect is mostly below 60% (Zhang Hua, Song Baoan, Pesticides, 2002, 41 (2), 6-9.)

Method used

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  • Aromatic amine schiff base derivative of gossypol and preparation method and plant-virus resisting application thereof
  • Aromatic amine schiff base derivative of gossypol and preparation method and plant-virus resisting application thereof
  • Aromatic amine schiff base derivative of gossypol and preparation method and plant-virus resisting application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of gossypol-aniline Schiff base (3):

[0023]

[0024] In a 100mL round bottom bottle, add 0.50g (0.86mmol) of gossypol acetate and 40mL of absolute ethanol, and then add 0.16g (1.73mmol) of aniline after fully dissolving. The reaction solution was heated to reflux for 5 hours. After naturally cooling to room temperature, the reaction solution was filtered, and the solid was recrystallized from benzene, then suction filtered and dried to obtain the target compound. Yield, 95%; melting point: 252-253°C; 1 H NMR (400MHz, CDCl 3 )δ10.17(d, J=12.3Hz, 2H), 7.89(s, 2H), 7.64(s, 2H), 7.37(t, J=7.5Hz, 4H), 7.30(d, J=7.9Hz, 2H), 7.19(t, J=6.9Hz, 2H), 5.77(s, 2H), 3.70-3.77(m, 2H), 2.16(s, 6H), 1.51-1.57(m, 12H); HRMS[ESI ]calcd for C 42 h 39 N 2 o 6 (M-H)-667.2814; found, 667.2812.

Embodiment 2

[0025] Embodiment 2: the synthesis of gossypol-4-sodium sulfonic acid aniline Schiff base (11)

[0026]

[0027] In a 100mL round bottom bottle, add 0.11g (2.59mmol) of sodium hydroxide, 40mL of absolute ethanol, and 0.30g (1.73mmol) of p-aminobenzenesulfonic acid, heat and reflux for 1 hour to generate sodium salt, then add 0.50mL of gossypol acetate g (0.86 mmol), continued heating for 5 hours, cooled to room temperature, filtered with suction, and recrystallized with isopropanol and methanol to obtain 0.27 g of a purple solid. Yield: 36%; Melting point >300°C; 1 H NMR (400MHz, DMSO-d 6 )δ14.94(d, J=11.7Hz, 2H), 10.41(d, J=11.7Hz, 2H), 8.58(s, 2H), 8.34(s, 2H), 7.64(d, J=8.0Hz, 4H), 7.52(s, 2H), 7.29(d, J=8.0Hz, 4H), 3.80-3.70(m, 2H), 2.00(s, 6H), 1.52-1.43(m, 12H).HRMS[ESI ]calcd for C 42 h 39 N 2 o 12 S 2 (M-2Na+H) - 827.1950, found 827.1928.

Embodiment 3

[0028] Embodiment 3: the synthesis of aromatic amine Schiff base derivatives 4-10, 12-22, 24-25 of gossypol: complete by repeating the method of Example 1

[0029] Synthesis of gossypol-4-methylaniline Schiff base (4):

[0030] Orange solid. Yield: 95%; Melting point: 246-248°C; 1 H NMR (400MHz, CDCl 3 )δ10.14(d, J=12.3Hz, 2H), 7.91(s, 2H), 7.63(s, 2H), 7.20(d, J=8.35Hz, 4H), 7.15(d, J=8.35Hz, 4H), 5.75(s, 2H), 3.71-3.77(m, 2H), 2.33(s, 6H), 2.15(s, 6H), 1.55(d, J=6.0Hz, 12H); HRMS[ESI]calcdfor C 44 h 43 N 2 o 6 (M-H) - , 695.3127; found, 695.3139.

[0031] Synthesis of gossypol-4-methoxyaniline Schiff base (5):

[0032] Dark yellow solid. Yield, 60%; Melting point: 272-274°C; 1 H NMR (400MHz, CDCl 3 )δ15.08(d, J=12.0Hz, 2H), 10.09(d, J=12.0Hz, 2H), 7.90(s, 2H), 7.63(s, 2H), 7.24(d, J=9.0Hz, 4H), 6.89(d, J=9.0Hz, 4H), 5.75(s, 2H), 3.79(s, 6H), 3.77-3.70(m, 2H), 2.15(s, 6H), 1.57-1.54(m , 12H).HRMS[ESI]calcd for C 44 h 45 N 2 o8 (M+H) + , 729.3170; found, 729.3...

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Abstract

The present invention relates to a gossypol aromatic amine Schiff base derivative as shown by general formula (I) and a preparation thereof and a use thereof in pesticides. This type of compound represents a novel and simple type of anti-viral structure. The synthetic method is simple and practical, and is thus easily industrially amplified. The gossypol aromatic amine Schiff base compounds used as a novel plant virus resistant agent can inhibit the following viruses well: tobacco mosaic virus, pepper virus, rice virus, tomato virus, sweet potato virus, potato virus, melon virus and maize dwarf mosaic virus, etc., and can efficiently prevent and treat viral diseases in many crops as follows: tobacco, peppers, rice, tomatoes, sweet potatoes, potatoes, melons and maize, etc., and is especially suitable for preventing and treating the tobacco mosaic disease. (See the description for the meaning of Ar therein).

Description

technical field [0001] The invention relates to an aromatic amine Schiff base derivative of gossypol and its preparation and anti-plant virus application, belonging to the technical field of pesticides. Background technique [0002] Gossypol (structural formula 1) mainly exists in cottonseed, accounting for 0.4%-1.7% of the total weight of cottonseed. Gossypol has a very wide range of biological activities: almost all cancer cells have inhibitory activity; can inhibit a variety of viruses, such as HIV, avian influenza, etc., which are now difficult to treat; have anti-parasitic activity (malaria, trypanosomiasis, etc.) ; It has bactericidal and insecticidal activity, and the content of gossypol compounds in the cotton plant and the ratio of different substances will be affected by external bacteria and insects; it also has antioxidant activity, and it has also shown its application in rubber and chemical fields etc. (Xu Zhihong, China Oils, 2008, 33(8), 6-10). Therefore, t...

Claims

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Application Information

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IPC IPC(8): C07C251/24C07C249/02C07C225/16C07C221/00C07C309/46C07C309/49C07C303/32A01N41/04A01N35/10A01N35/06A01P1/00
CPCC07C225/16A01N35/10A01N41/04C07C309/46C07C309/49
Inventor 汪清民李玲刘玉秀李永强李铮王开亮
Owner NANKAI UNIV
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