Chalcone derivative containing 4-quinazolone structure as well as preparation method and application of chalcone derivative

Abstract

The invention relates to the technical field of chemical engineering, in particular to a chalcone derivative containing a 4-quinazolone structure as well as a preparation method and application of the chalcone derivative. The specific technical scheme is as follows: the structural formula is as follows: # imgabs0 #, when R1 is not a hydrogen atom, R1 contains one methyl, methoxyl or halogen atom at ortho-position or meta-position, and R2 is nitro or halogen atom. According to the invention, (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl) propan-2-ene-1-ketone and 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazoline-4 (3H)-ketone with excellent biological activity are subjected to a reaction to generate the chalcone derivative containing a 4-quinazolinone structure, and the chalcone derivative has relatively good inhibitory activity on tobacco mosaic virus; the compound can be used as a potential anti-plant-virus agent.

Description

Technical Field

[0001] The invention relates to the technical field of chemical engineering, and in particular to a chalcone derivative containing a 4-quinazolone structure and a preparation method and application thereof. Background Art

[0002] As an important flavonoid natural product, chalcone has attracted much attention due to its various biological activities, including antiviral, antibacterial, antioxidant, and anticancer. In the technical background of anti-plant virus TMV (tobacco mosaic virus), a series of progress has been made in the research and application of chalcone and its derivatives:

[0003] In 2017, Gan et al. (Eur. J. Med. Chem, 2017, 65: 4367-4377) synthesized a series of chalcone derivatives containing ferulic acid. The antiviral biological activity test results showed that most of the target compounds had a certain inhibitory effect on TMV. The bioassay results showed that compounds F3, F6, F17 and F27 showed significant therapeutic, protective and inactivating activities against TMV. In particular, compound F27, whose 50% effective concentration (EC 50 ) value was 98.78 μg / mL, showing the best protective activity.

[0004] In 2020, Fu et al. (RSC. Adv, 2020, 10: 24483–24490) designed and synthesized 28 chalcone derivatives containing purine thioethers and tested their antiviral activity. Preliminary test results showed that the synthesized compounds all had good anti-TMV activity. Some of the compounds had excellent therapeutic activity, which was better than the control drug ribavirin.

[0005] In 2023, Hu et al. (Arab. J. Chem, 2023, 16: 104776-104786) designed and synthesized 24 chalcone derivatives containing indole sulfide. After antiviral activity testing, the test results showed that D11 had good activity in treating and protecting plants against TMV, which was better than the control agent Ningnanmycin;

[0006] In 2024, Mao et al. (MOL DIVERS, 2024, DOI: 10.1007 / s11030-024-10843-7) designed and synthesized 28 phenoxypyridine-containing chalcone derivatives and tested their antiviral activity. The experimental results showed that most of the compounds had good anti-TMV activity, among which L4 had excellent activity in therapeutic and protective activity, which was better than the control agent Ningnanmycin.

[0007] In summary, there is no report on introducing 4-quinazolinone structure into chalcone derivatives and testing their anti-plant virus activity. Summary of the invention

[0008] In view of the deficiencies in the prior art, the present invention provides a chalcone derivative containing a 4-quinazolone structure and a preparation method and application thereof.

[0009] To achieve the above objectives, the present invention is implemented through the following technical solutions:

[0010] The present invention discloses a chalcone derivative containing a 4-quinazolone structure, the structural formula of which is shown in the following formula (I):

[0011]

[0012] Among them, when R 1 When it is not a hydrogen atom, R 1 The ortho or meta position contains a methyl, methoxy or halogen atom, R 2 It is a nitro group or a halogen atom. The halogen atom is fluorine, chlorine or bromine.

[0013] Accordingly, a method for preparing a chalcone derivative containing a 4-quinazolone structure comprises the following steps:

[0014] (1) Using p-hydroxyacetophenone and various substituted benzaldehydes as raw materials and ethanol as solvent, (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one is prepared under alkaline conditions;

[0015] (2) Using (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one as raw material, K 2 CO 3 as an acid-binding agent and acetonitrile as a solvent to react with 1,3-dibromopropane to prepare (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one;

[0016] (3) Using 2-amino-5-substituted benzoic acid as a raw material, acetic anhydride is added to prepare 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one;

[0017] (4) 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one reacts with 4-aminophenol to prepare 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one;

[0018] (5) (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one and 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one, in K 2 CO 3 With acetonitrile as solvent and acid-binding agent, etherification reaction occurs to generate chalcone derivatives containing 4-quinazolone structure.

[0019] Preferably, in step (1), the amount of p-hydroxyacetophenone is 4 to 20 mmol, and the amount of substituted benzaldehyde is 5 to 20 mmol;

[0020] In step (2), the amount of (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one is 2 to 10 mmol, K 2 CO 3 The dosage of is 6-20 mmol, and the dosage of 1,3-dibromopropane is 5-20 mmol;

[0021] In step (3), the amount of 2-amino-5-substituted benzoic acid is 5 to 10 mmol, and the amount of acetic anhydride solution is 0.05 to 0.15 mol;

[0022] In step (4), the amount of 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one is 5 to 15 mmol, and the amount of 4-aminophenol is 5 to 15 mmol;

[0023] In step (5), the amount of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one is 1 to 10 mmol, the amount of 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one is 1 to 5 mmol, and the amount of K 2 CO 3 The dosage is 4 to 10 mmol.

[0024] Correspondingly, the above-mentioned chalcone derivative containing a 4-quinazolone structure or the chalcone derivative containing a 4-quinazolone structure prepared by the above-mentioned preparation method is used in anti-plant virus agents.

[0025] Preferably, the plant virus is tobacco mosaic virus.

[0026] The present invention has the following beneficial effects:

[0027] 1. The present invention uses p-hydroxyacetophenone and various substituted benzaldehydes to undergo aldol condensation reaction to generate 1-(4-hydroxyphenyl)-3-(substituted aromatic)-2-propene-1-one, and 1-(4-hydroxyphenyl)-3-(substituted aromatic)-2-propene-1-one reacts with 1,3-dibromopropane to prepare 1-(4-(3-bromopropoxy)phenyl)-3-(substituted aromatic)-2-propene-1-one. 2-amino-5-substituted benzoic acid is added to acetic anhydride to prepare 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one, 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one is reacted with 4-aminophenol to prepare 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one, (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one is etherified with 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one to generate chalcone derivatives containing 4-quinazolinone structure. This preparation method uses p-hydroxyacetophenone, various substituted benzaldehydes and 2-amino-5-substituted benzoic acid as raw materials, which are all common organic reagents and solvents, and the raw materials are easy to obtain. In addition, the method has mild reaction conditions, simple post-treatment and high yield, which can reach between 50% and 90%.

[0028] 2. The present invention uses (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one to react with 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one having excellent biological activity to generate chalcone derivatives containing a 4-quinazolinone structure. The anti-plant virus activity of the target compound was determined at a concentration of 500 μg / mL. The test results show that: at the experimental test concentration, it has good inhibitory activity against tobacco mosaic virus and can be used as a potential anti-plant virus agent. DETAILED DESCRIPTION

[0029] The following will be described clearly and completely in conjunction with the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0030] Unless otherwise specified, the technical means used in the embodiments are conventional means well known to those skilled in the art.

[0031] Overall embodiment

[0032] A chalcone derivative containing a 4-quinazolone structure, the structural formula of which is shown in the following formula (I):

[0033]

[0034] Among them, when R 1 When it is not a hydrogen atom, R 1 Contains a methyl, methoxy or halogen atom at the ortho or meta position; R 2 It is a nitro group or a halogen atom. The halogen atom is fluorine, chlorine or bromine.

[0035] The method for preparing the derivative comprises the following steps:

[0036] (1) Using p-hydroxyacetophenone (4-20 mmol) and various substituted benzaldehydes (5-20 mmol) as raw materials and ethanol (30-80 mL) as solvent, 1-(4-hydroxyphenyl)-3-(substituted phenyl)-2-propen-1-one was prepared under alkaline conditions of 5% sodium hydroxide solution (10-30 mL);

[0037]

[0038] (2) Using (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one (2-10 mmol) as a raw material, 2 CO 3 (6-20 mmol) as an acid-binding agent and acetonitrile (25-50 mL) as a solvent with 1,3-dibromopropane (5-20 mmol) to prepare 1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one;

[0039]

[0040] (3) 2-amino-5-substituted benzoic acid (5-10 mmol) was used as a raw material, and acetic anhydride (0.05-0.15 mol) was added to prepare 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one;

[0041]

[0042] (4) 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one (5-15 mmol) was reacted with 4-phenol (5-15 mmol) to prepare 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one;

[0043]

[0044] (5) (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one (1-10 mmol) and 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one (1-5 mmol) were reacted in K 2 CO 3 (4-10 mmol) as an acid-binding agent and acetonitrile (20-50 mL) as a solvent to produce chalcone derivatives containing a 4-quinazolone structure.

[0045]

[0046] The present invention will be further described below in conjunction with specific embodiments.

[0047] Example 1

[0048] The synthesis of (E)-6-fluoro-2-methyl-3-(4-(4-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one (compound number T1) comprises the following steps:

[0049] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one: 4-hydroxyacetophenone (1.20 g), p-methylbenzaldehyde (1.03 g) and 50 mL of ethanol were added to a round-bottom flask, and 10 mL of 5% sodium hydroxide solution was slowly added dropwise under an ice bath, and stirred under electromagnetic stirring for about 10 to 12 hours. After the reaction was completed, the mixed solution was poured into a 1000 mL beaker filled with ice water, and the pH was adjusted to 5 to 6 with a 5% dilute hydrochloric acid solution. A large amount of light yellow solid precipitated, and the solid was filtered under reduced pressure, and finally recrystallized with an ethanol / water system (1:2) to obtain a light yellow solid with a yield of 90%.

[0050] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one: (E)-1-(4-hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one (0.7 g), K 2 CO 3 (1.29g), 1,3-dibromopropane (0.9mL) and 25mL acetonitrile were added to a 100mL round-bottom flask, the temperature was controlled at about 85°C, and the mixture was stirred for 60min under electromagnetic stirring, and then 1,3-dibromopropane (0.9mL) was slowly added dropwise for 5-6h. After the reaction was completed, the system was transferred to a beaker containing 50mL ice water, and a white solid precipitated. The solid was filtered under reduced pressure, and the filter cake was washed with petroleum ether to obtain a white solid with a yield of 93%.

[0051] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: 1.0 g of 2-amino-5-fluorobenzoic acid was reacted in acetic anhydride (6.05 mL) at 140° C. for 8 hours. After TLC detection showed that the reaction was complete, the product was distilled under reduced pressure to obtain a pale yellow solid with a yield of 95%.

[0052] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: 1.10 g of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one was added to 4-aminophenol (0.74 g) at 120°C, dissolved in 50 mL of glacial acetic acid, and heated to react for 8 hours. After the reaction was completed as detected by TLC, the mixture was filtered and washed with water and n-hexane in turn to obtain 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one.

[0053] (5) Synthesis of (E)-6-fluoro-2-methyl-3-(4-(4-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one: 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one (0.50 g), K 2 CO 3 (0.76 g) and 30 mL CH 3 CN was added to a 100 mL round-bottom flask, and after reflux at 80°C for 60 min, (E)-1-(4-(3-bromopropoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one (0.86 g) was added to the reaction system, and the reaction was continued by heating and reflux for 8 h. The reaction system was concentrated under reduced pressure to remove part of the solvent, and then poured into 500 mL of ice water, and a white solid was precipitated. The reaction mixture was allowed to stand, filtered, and recrystallized from anhydrous ethanol to obtain a crude product, which was purified by column chromatography (petroleum ether: ethyl acetate = 4:1, v / v) to obtain (E)-6-fluoro-2-methyl-3-(4-(4-(3-(p-tolyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one as a white solid with a yield of 65%.

[0054] Example 2

[0055] The synthesis of (E)-6-chloro-2-methyl-3-(4-(4-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one (compound number T2) comprises the following steps:

[0056] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one: as in Example 1, step (1).

[0057] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one: as in Example 1, step (2).

[0058] (3) Synthesis of 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-chlorobenzoic acid is used as the starting material.

[0059] (4) Synthesis of 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0060] (5) Synthesis of (E)-6-chloro-2-methyl-3-(4-(4-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one: As in step (5) of Example 1, except that 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one is used as the raw material.

[0061] Example 3

[0062] The synthesis of (E)-6-bromo-2-methyl-3-(4-(4-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one (compound number T3) comprises the following steps:

[0063] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one: as in Example 1, step (1).

[0064] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one: as in Example 1, step (2).

[0065] (3) Synthesis of 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-chlorobenzoic acid is used as the starting material.

[0066] (4) Synthesis of 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0067] (5) Synthesis of (E)-6-bromo-2-methyl-3-(4-(4-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one: As in step (5) of Example 1, except that 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one is used as the raw material.

[0068] Example 4

[0069] The synthesis of (E)-2-methyl-6-nitro-3-(4-(3-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one (compound number T4) comprises the following steps:

[0070] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-(p-tolyl)prop-2-en-1-one: as in Example 1, step (1).

[0071] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(p-tolyl)prop-2-en-1-one: as in Example 1, step (2).

[0072] (3) Synthesis of 2-methyl-6-nitro-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-nitrobenzoic acid is used as the starting material.

[0073] (4) Synthesis of 3-(4-hydroxyphenyl)-2-methyl-6-nitroquinazolin-4(3H)-one: As in step (4) of Example 1, except that 2-methyl-6-nitro-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0074] (5) Synthesis of (E)-2-methyl-6-nitro-3-(4-(3-(3-(p-methylphenyl)acryloyl)phenoxy)propoxy)phenyl)quinazolin-4(3H)-one: as in step (5) of Example 1, except that 3-(4-hydroxyphenyl)-2-methyl-6-nitroquinazolin-4(3H)-one is used as the raw material.

[0075] Example 5

[0076] The synthesis of 3-(4-(3-(4-cinnamoylphenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one (compound number T5) comprises the following steps:

[0077] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one: As in step (1) of Example 1, except that benzaldehyde is used as the raw material.

[0078] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-phenylprop-2-en-1-one: as in step (2) of Example 1, except that (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one is used as the raw material.

[0079] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0080] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0081] (5) Synthesis of 3-(4-(3-(4-cinnamoylphenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one: As in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-phenylprop-2-en-1-one was used as the starting material.

[0082] Example 6

[0083] The synthesis of 6-chloro-3-(4-(3-(4-cinnamoylphenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T6) comprises the following steps:

[0084] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one: As in step (1) of Example 1, except that benzaldehyde is used as the raw material.

[0085] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-phenylprop-2-en-1-one: as in step (2) of Example 1, except that (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one is used as the raw material.

[0086] (3) Synthesis of 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-chlorobenzoic acid is used as the starting material.

[0087] (4) Synthesis of 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0088] (5) Synthesis of 6-chloro-3-(4-(3-(4-cinnamoylphenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: As in step (5) of Example 1, except that 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one and (E)-1-(4-(3-bromopropoxy)phenyl)-3-phenylprop-2-en-1-one were used as raw materials.

[0089] Example 7

[0090] The synthesis of 6-bromo-3-(4-(3-(4-cinnamoylphenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T7) comprises the following steps:

[0091] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one: As in step (1) of Example 1, except that benzaldehyde is used as the raw material.

[0092] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-phenylprop-2-en-1-one: as in step (2) of Example 1, except that (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one is used as the raw material.

[0093] (3) Synthesis of 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-bromobenzoic acid is used as the starting material.

[0094] (4) Synthesis of 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0095] (5) Synthesis of 6-bromo-3-(4-(3-(4-cinnamoylphenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: As in step (5) of Example 1, except that 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one and (E)-1-(4-(3-bromopropoxy)phenyl)-3-phenylprop-2-en-1-one were used as raw materials.

[0096] Example 8

[0097] The synthesis of (E)-6-chloro-3-(4-(4-(3-(4-fluorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T8) comprises the following steps:

[0098] (1) Synthesis of (E)-3-(4-fluorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that p-fluorobenzaldehyde is used as the raw material.

[0099] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-fluorophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(4-fluorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0100] (3) Synthesis of 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-chlorobenzoic acid is used as the starting material.

[0101] (4) Synthesis of 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0102] (5) Synthesis of (E)-6-chloro-3-(4-(4-(3-(4-fluorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-fluorophenyl)prop-2-en-1-one and 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one are used as raw materials.

[0103] Example 9

[0104] The synthesis of (E)-6-bromo-3-(4-(4-(3-(4-fluorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T9) comprises the following steps:

[0105] (1) Synthesis of (E)-3-(4-fluorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that p-fluorobenzaldehyde is used as the raw material.

[0106] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-fluorophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(4-fluorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0107] (3) Synthesis of 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-bromobenzoic acid is used as the starting material.

[0108] (4) Synthesis of 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0109] (5) Synthesis of (E)-6-bromo-3-(4-(4-(3-(4-fluorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-fluorophenyl)prop-2-en-1-one and 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one are used as raw materials.

[0110] Example 10

[0111] The synthesis of (E)-3-(4-(3-(4-(2,4-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one (compound number T10) comprises the following steps:

[0112] (1) Synthesis of (E)-3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that 2,4-dichlorobenzaldehyde is used as the raw material.

[0113] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0114] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0115] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0116] (5) Synthesis of (E)-3-(4-(3-(4-(2,4-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one is used as the raw material.

[0117] Embodiment 11

[0118] The synthesis of (E)-6-chloro-3-(4-(3-(4-(2,4-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T11) comprises the following steps:

[0119] (1) Synthesis of (E)-3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that 2,4-dichlorobenzaldehyde is used as the raw material.

[0120] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0121] (3) Synthesis of 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-chlorobenzoic acid is used as the starting material.

[0122] (4) Synthesis of 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0123] (5) Synthesis of (E)-6-chloro-3-(4-(3-(4-(2,4-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one and 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one are used as raw materials.

[0124] Example 12

[0125] The synthesis of (E)-6-bromo-3-(4-(3-(4-(2,4-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T12) comprises the following steps:

[0126] (1) Synthesis of (E)-3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that 2,4-dichlorobenzaldehyde is used as the raw material.

[0127] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(2,4-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0128] (3) Synthesis of 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-bromobenzoic acid is used as the starting material.

[0129] (4) Synthesis of 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-bromo-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0130] (5) Synthesis of (E)-6-bromo-3-(4-(3-(4-(2,4-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: As in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,4-dichlorophenyl)prop-2-en-1-one and 6-bromo-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one are used as raw materials.

[0131] Embodiment 13

[0132] The synthesis of (E)-3-(4-(3-(4-(4-chlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one (compound number T13) comprises the following steps:

[0133] (1) Synthesis of (E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that p-chlorobenzaldehyde is used as the raw material.

[0134] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-chlorophenyl)prop-2-en-1-one: As in step (2) of Example 1, except that (E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0135] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0136] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0137] (5) Synthesis of (E)-3-(4-(3-(4-(4-chlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-chlorophenyl)prop-2-en-1-one is used as the raw material.

[0138] Embodiment 14

[0139] The synthesis of (E)-3-(4-(3-(4-(4-bromophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one (compound number T14) comprises the following steps:

[0140] (1) Synthesis of (E)-3-(4-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that p-bromobenzaldehyde is used as the raw material.

[0141] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-bromophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(4-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0142] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0143] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0144] (5) Synthesis of (E)-3-(4-(3-(4-(4-bromophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-bromophenyl)prop-2-en-1-one is used as the raw material.

[0145] Embodiment 15

[0146] The synthesis of (E)-3-(4-(3-(4-(4-bromophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-chloro-2-methylquinazolin-4(3H)-one (compound number T15) comprises the following steps:

[0147] (1) Synthesis of (E)-3-(4-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that p-bromobenzaldehyde is used as the raw material.

[0148] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-bromophenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(4-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0149] (3) Synthesis of 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: As in step (3) of Example 1, except that 2-amino-5-chlorobenzoic acid is used as the starting material.

[0150] (4) Synthesis of 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: As in step (4) of Example 1, except that 6-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one was used as the starting material.

[0151] (5) Synthesis of (E)-3-(4-(3-(4-(4-bromophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-chloro-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-bromophenyl)prop-2-en-1-one and 6-chloro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one are used as raw materials.

[0152] Example 16

[0153] The synthesis of (E)-6-fluoro-3-(4-(3-(4-(4-methoxyphenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one (compound number T16) comprises the following steps:

[0154] (1) Synthesis of (E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one: as in step (1) of Example 1, except that p-methoxybenzaldehyde is used as the raw material.

[0155] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one: As in step (2) of Example 1, except that (E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one is used as the raw material.

[0156] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0157] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0158] (5) Synthesis of (E)-6-fluoro-3-(4-(3-(4-(4-methoxyphenyl)acryloyl)phenoxy)propoxy)phenyl)-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one is used as the raw material.

[0159] Embodiment 17

[0160] The synthesis of (E)-3-(4-(3-(4-(2,6-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one (compound number T17) comprises the following steps:

[0161] (1) Synthesis of (E)-3-(2,6-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: As in step (1) of Example 1, except that 2,6-dichlorobenzaldehyde is used as the raw material.

[0162] (2) Synthesis of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one: As in step (2) of Example 1, except that (E)-3-(2,6-dichlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0163] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0164] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0165] (5) Synthesis of (E)-3-(4-(3-(4-(2,6-dichlorophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-1-(4-(3-bromopropoxy)phenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one is used as the raw material.

[0166] Embodiment 18

[0167] The synthesis of (E)-3-(4-(3-(3-(bromophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one (compound number T18) comprises the following steps:

[0168] (1) Synthesis of (E)-3-(3-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one: as in step (1) of Example 1, except that m-bromobenzaldehyde is used as the raw material.

[0169] (2) Synthesis of (E)-3-(3-bromophenyl)-1-(4-(3-bromopropoxy)phenyl)prop-2-en-1-one: as in step (2) of Example 1, except that (E)-3-(3-bromophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one is used as the raw material.

[0170] (3) Synthesis of 6-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one: as in step (3) of Example 1.

[0171] (4) Synthesis of 6-fluoro-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one: as in step (4) of Example 1.

[0172] (5) Synthesis of (E)-3-(4-(3-(3-bromophenyl)acryloyl)phenoxy)propoxy)phenyl)-6-fluoro-2-methylquinazolin-4(3H)-one: as in step (5) of Example 1, except that (E)-3-(3-bromophenyl)-1-(4-(3-bromopropoxy)phenyl)prop-2-en-1-one is used as the raw material.

[0173] The physicochemical properties and mass spectrometry data of the synthesized chalcone derivatives containing 4-quinazolone structure are shown in Table 1. 1 H NMR), carbon spectrum ( 13 C NMR) and fluorine spectra ( 19 F NMR) data are shown in Table 2.

[0174] Table 1 Physicochemical properties of target compounds and their mass spectrometry analysis data

[0175]

[0176]

[0177] Table 2 H NMR, C NMR and F NMR data of target compounds

[0178]

[0179]

[0180]

[0181]

[0182] Activity test example Anti-tobacco mosaic virus activity test

[0183] Test Method

[0184] A. Virus purification

[0185] The Luo Chaopeng method (Luo Chaopeng et al., Tobacco Science and Technology, 2012, 10: 77-80.) was used to select the upper leaves of the host Nicotiana tabacum.L plants that had been inoculated for more than 3 weeks and infected by TMV system. The leaves were homogenized in phosphate buffer, filtered through double gauze, centrifuged at 8000r / min, treated with polyethylene glycol twice, and centrifuged again. The precipitate was suspended in phosphate buffer to obtain the TMV extract. The entire experiment was carried out at 4°C. The absorbance value at a wavelength of 260nm was measured using an ultraviolet spectrophotometer, and the virus concentration was calculated according to the formula.

[0186]

[0187] Where E represents the extinction coefficient, TMV It is 3.1.

[0188] B. In vivo therapeutic effect of the agent on TMV infection

[0189] Therapeutic effect of the drug on the infection: Select the heart-leaf tobacco with the same growth of 5 to 6 leaves, top it, sprinkle corundum evenly on the whole leaf, and use a brush to dip the virus juice (6×10 -3 mg / mL) whole leaves were inoculated with virus, dried naturally and then rinsed with clean water. After the leaves were dry, the left half of the leaves were lightly coated with the agent using a brush, and the right half of the leaves were coated with a solvent of the corresponding concentration as a control. After 2 to 4 days, the number of dead spots was recorded and the inhibition rate was calculated according to the following formula.

[0190] C. The protective effect of the agent on TMV infection in vivo

[0191] The protective effect of the agent on TMV infection: Select the heart-leaf tobacco with the same growth of 5 to 6 leaves to top, and use a brush to gently apply the agent on the left half of the leaf, and apply the solvent of the corresponding concentration on the right half of the leaf as a control. After 24 hours, sprinkle corundum evenly on the whole leaf, and use a brush to dip the virus juice (6×10 -3 mg / mL) whole leaves were inoculated with the virus and rinsed with clean water. The number of dead spots was recorded after 2 to 4 days, and the inhibition rate was calculated according to the following formula.

[0192] D. The inactivation effect of the agent on TMV infection in vivo

[0193] Mix the agent with an equal volume of virus juice and passivate for 30 minutes. Use a brush to dip the mixture of the agent and the virus, and rub it on the left half of the leaf sprinkled with emery. The lower part of the leaf is supported by a flat wooden board. Sterile water and virus juice are mixed and inoculated on the right half of the leaf. Three plants are set up for each agent treatment, each with 5 to 6 leaves. Then the plants are placed in a light incubator for moisturizing cultivation, the temperature is controlled at 23±1℃, the light is 10000Lux, and the number of dead spots produced is observed and recorded after 2 to 4 days. The inhibition rate is calculated according to the following formula.

[0194] Inhibition rate = (average number of dead spots on the half leaf without the drug - average number of dead spots on the half leaf with the drug) / average number of dead spots on the half leaf without the drug × 100%

[0195] Among them, the average number of necrotic spots on the half leaf without the pesticide and the number of necrotic spots on the half leaf with the pesticide were the average of three repetitions in each group.

[0196] The results of the anti-tobacco mosaic virus biological activity test are shown in Table 3 below.

[0197] Table 3 Protective, therapeutic and inactivating activities of target compounds against tobacco mosaic virus

[0198]

[0199]

[0200] a: Average value of three parallel tests.

[0201] b: The commercial drug Ningnanmycin was used as the positive control drug.

[0202] The therapeutic and protective activities of target compounds T1 to T18 against tobacco mosaic virus (TMV) were tested using the half-leaf spot method and the commercial drug Ningnanmycin as the control at a test concentration of 500 μg / mL (see Table 3). The test results showed that most of the target compounds had good therapeutic and protective activities against TMV. Among them, the therapeutic activity inhibition rates of compounds T3, T5 and T16 were 69.4, 68.6 and 71.9%, respectively, which were better than the control drug Ningnanmycin (65.7%). The protective activity inhibition rates of compounds T3, T14 and T16 were 68.2, 68.8 and 71.1%, respectively. They were all better than Ningnanmycin (62.3%).

[0203] The above experimental activity data show that chalcone derivatives containing 4-quinazolone structure have a certain inhibitory effect on plant viruses (TMV), among which some target compounds show excellent activity against plant viruses and can be used as potential anti-plant virus drugs with good application prospects.

[0204] The embodiments described above are only descriptions of the preferred modes of the present invention, and are not intended to limit the scope of the present invention. Without departing from the design spirit of the present invention, various modifications and improvements made to the technical solutions of the present invention by ordinary technicians in this field should all fall within the protection scope determined by the claims of the present invention.

Claims

1. A chalcone derivative containing a 4-quinazolone structure, characterized in that: Its structural formula is shown below: Wherein, when R1 is not a hydrogen atom, R1 contains a methyl group, a methoxy group or a halogen atom at the ortho or meta position, and R2 is a nitro group or a halogen atom.

2. A chalcone derivative containing a 4-quinazolone structure according to claim 1, characterized in that: The halogen atom is fluorine, chlorine or bromine.

3. A method for preparing a chalcone derivative containing a 4-quinazolone structure as claimed in claim 1 or 2, characterized in that: The following steps are involved: (1) Using p-hydroxyacetophenone and various substituted benzaldehydes as raw materials and ethanol as solvent, (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one is prepared under alkaline conditions; (2) using (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one as a raw material, K2CO3 as an acid-binding agent, and acetonitrile as a solvent to react with 1,3-dibromopropane to prepare (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one; (3) 2-amino-5-substituted benzoic acid is used as a raw material, and acetic anhydride is added to prepare 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one; (4) 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one reacts with 4-aminophenol to prepare 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one; (5) (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one and 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazolin-4(3H)-one undergo etherification reaction in the presence of K2CO3 as an acid binder and acetonitrile as a solvent to generate chalcone derivatives containing a 4-quinazolone structure.

4. The method for preparing a chalcone derivative containing a 4-quinazolone structure according to claim 3, characterized in that: In step (1), the amount of p-hydroxyacetophenone is 4 to 20 mmol, and the amount of substituted benzaldehyde is 5 to 20 mmol; In step (2), the amount of (E)-1-(4-hydroxyphenyl)-3-(substituted phenyl)prop-2-en-1-one is 2 to 10 mmol, the amount of K2CO3 is 6 to 20 mmol, and the amount of 1,3-dibromopropane is 5 to 20 mmol; In step (3), the amount of 2-amino-5-substituted benzoic acid used is 5 to 10 mmol, and the amount of acetic anhydride solution used is 0.05 to 0.15 mol; In step (4), the amount of 6-substituted-2-methyl-4H-benzo[d][1,3]oxazin-4-one is 5 to 15 mmol, and the amount of 4-aminophenol is 5 to 15 mmol; In step (5), the amount of (E)-1-(4-(3-bromopropoxy)phenyl)-3-(substituted phenyl)prop-2-en-1-one is 1 to 10 mmol, the amount of 6-substituted-3-(4-hydroxyphenyl)-2-methylquinazoline-4(3H)-one is 1 to 5 mmol, and the amount of K2CO3 is 4 to 10 mmol.

5. Use of a chalcone derivative containing a 4-quinazolone structure as claimed in any one of claims 1 to 2 or a chalcone derivative containing a 4-quinazolone structure prepared according to any one of claims 3 to 4 in the preparation of an anti-plant virus agent.

6. The use according to claim 5, characterized in that: The plant virus is tobacco mosaic virus.

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