N-aryl quinazoline and sulfo-imidazolinone compound as well as preparation method and application of N-aryl quinazoline and sulfo-imidazolinone compound

Abstract

The invention discloses an N-aryl quinazoline thio-imidazolinone compound and a preparation method and application thereof.The N-aryl quinazoline thio-imidazolinone compound is prepared by the steps that 2-amino benzylamine and a phenyl isothiocyanate compound serve as raw materials and react in dichloromethane under the action of triethylamine to generate a 1-(2-aminobenzyl)-3-phenylthiourea compound, and the 1-(2-aminobenzyl)-3-phenylthiourea compound is subjected to post-treatment to obtain the N-aryl quinazoline thio-imidazolinone compound. And reacting the 1-(2-aminobenzyl)-3-phenylthiourea compound with ethyl glyoxylate, so as to obtain the N-aryl quinazoline and thioimidazolinone compound. The preparation method comprises the following steps of: reacting the 1-(2-aminobenzyl)-3-phenylthiourea compound with ethyl glyoxylate; the raw materials for synthesis of the compound are easy to obtain, the synthesis method is simple, and meanwhile, the compound has a good inhibition effect on the activity of crop germs, especially on sclerotinia sclerotiorum, phytophthora germs, gibberellic disease germs, magnaporthe oryzae, botrytis cinerea and rhizoctonia solani.

Description

Technical Field

[0001] The present invention belongs to the technical field of medicines and pharmaceuticals, and in particular relates to an N-arylquinazoline-thioimidazolone compound, a preparation method thereof and a use thereof. Background Art

[0002] Quinazoline compounds are a hot topic in pharmaceutical and pesticide research due to their broad biological activity and diverse structures. In the pesticide field, they can be used as highly effective insecticides, fungicides, and herbicides, playing a crucial role in ensuring the healthy growth of crops and increasing agricultural yields. In 2016, Bouley et al. designed a series of novel quinazoline derivatives based on the quinazoline scaffold and tested their activity against methicillin-resistant Staphylococcus aureus, Enterococcus faecalis, Klebsiella pneumoniae, Acetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp. The results demonstrated the antibacterial potential of (E)-2-(4-ethynylphenyl)-3-(3-hydroxyphenyl)quinazolin-4(3H)-one, making it a promising candidate for novel quinazoline antibacterial agents. In 2017, Jiang et al. designed and synthesized N-isopropyl-N-(4-(trifluoromethyl)benzyl)-3,4-dihydroquinazoline-2,4-diamine with an MIC of 3.9 μg / mL against Escherichia coli, which was superior to the antibiotics vancomycin and methicillin. In 2019, Shih-I Liu et al. provided a method for the synthesis of hydantoin tetrahydroisoquinoline and diketopiperazine tetrahydroisoquinoline with broad substrate range and enantioselectivity. In 2020, Qian et al. designed and synthesized (E)-3-(2-(4-cyanostyryl)-4-oxoquinazoline-3(4H)-yl)-4-fluorobenzoic acid, which showed synergistic effects with piperacillin-tazobactam (TZP) in in vitro and in vivo activity assays in a mouse model of MRSA infection. In 2023, Zhang et al. introduced amide into the quinazoline skeleton through an active splicing strategy and synthesized a series of novel quinazolinone drugs with amide structure, which have certain antibacterial activity against Pseudomonas syringae and bacterial blight.

[0003] Imidazolinone compounds are also a hot topic in drug and pesticide research. Their strong selectivity, broad herbicidal spectrum, low dosage, and environmental safety have led to their rapid adoption in agricultural production. In 2008, Li Ke et al. synthesized novel imidazoline-2,4-dionamide derivatives containing α-substituted phenoxypropionyl groups, which exhibited excellent fungicidal activity against cotton wilt pathogen, rice sheath blight pathogen, cucumber gray mold pathogen, wheat head blight pathogen, apple ring rot pathogen, and cotton anthracnose pathogen. In 2018, Han Jintao et al. synthesized 1-(phenoxyacetyl)-3-arylimidazoline-2,4-diones, which exhibited potent inhibitory effects on the growth of rapeseed and barnyardgrass. Compounds H3 and H5 both exhibited 100% inhibition against rapeseed. In 2020, Zhang Kun et al. designed and synthesized 2,4-imidazolidinedione cyclohexanesulfonamide compounds with excellent antibacterial effects against five common bacteria: cabbage soft rot pathogen, citrus canker pathogen, pepper scab pathogen, amylovora, and tomato canker pathogen.

[0004] However, with the increasing demand for practical applications and the increasing requirements for compound performance, the existing quinazoline and imidazoline dione compounds still have some limitations, and there are few reports on the research of thioimidazolinone compounds. Summary of the Invention

[0005] The technical problem to be solved by the present invention is to overcome the deficiencies of the prior art and provide an N-arylquinazolinothioimidazolinone compound, a preparation method thereof, and uses thereof. Based on the pharmacophore splicing principle and the pharmacodynamic superposition principle, a quinazoline ring structure and a thioimidazolinone ring structure unit are introduced into a single molecule to design and synthesize an N-arylquinazolinothioimidazolinone compound. The present invention mainly synthesizes an N-arylquinazolinothioimidazolinone compound and studies its antibacterial activity. The preparation method of this type of compound is simple, the raw materials are readily available, and the compound has good antibacterial activity against crop pathogens, particularly against pathogens such as fusarium head blight, phytophthora, rice blast, sclerotinia, gray mold, and sheath blight, thereby effectively ensuring the yield of crops.

[0006] In order to solve the above technical problems, the basic concept of the technical solution adopted by the present invention is:

[0007] In one aspect, the present invention provides an N-arylquinazolin-thioimidazolinone compound having the general structural formula (I):

[0008]

[0009] In formula (I), R is H or an alkyl group.

[0010] Preferably, R is one of H, methyl or butyl.

[0011] Preferably, the N-arylquinazolinone compound having the general structural formula (I) is selected from one or more of the following compounds:

[0012] N-phenylquinazolin-thioimidazolinone:

[0013]

[0014] N-(4-Methylphenyl)quinazolin-thioimidazolinone:

[0015]

[0016] N-(3-methylphenyl)quinazolin-thioimidazolinone:

[0017]

[0018] N-(4-n-butylphenyl)quinazolin-thioimidazolinone:

[0019]

[0020] Another aspect of the present invention provides a method for preparing N-arylquinazolin-thioimidazolinone compounds having the general structural formula (I), the method comprising the following steps:

[0021] S1) reacting 2-aminobenzylamine of structural formula (IV) with an aryl isothiocyanate compound of structural formula (III) in dichloromethane in the presence of triethylamine to obtain a thiourea compound of structural formula (II):

[0022]

[0023] S2) reacting a thiourea compound having the general structural formula (II) with ethyl glyoxylate to prepare an N-arylquinazolin-thioimidazolone compound having the general structural formula (I):

[0024]

[0025] In formula (I), R is H or alkyl;

[0026] Preferably, R is H, methyl or butyl.

[0027] Preferably, step S1) is specifically as follows: weighing 2-aminobenzylamine (1.221 g, 10 mmol) of the general formula (IV), aryl isothiocyanate (1.487 g, 11 mmol) of the general formula (III), and triethylamine (1.012 g, 10 mmol) into a 100 mL round-bottom flask, adding 45 mL of dichloromethane to dissolve, and reacting the reaction solution at room temperature. After the reaction is completed, the solvent is removed under reduced pressure, and the thiourea compound (II) is separated by column chromatography.

[0028] In the present invention, in step S1), the preferred reaction molar ratio of 2-aminobenzylamine having the general structural formula (IV), aryl isothiocyanate having the general structural formula (III), and triethylamine is 1:1.1:1, the preferred temperature is 25° C., and the preferred reaction time is 4 h.

[0029] Preferably, step S2) is specifically as follows: Compound II (0.772 g, 3 mmol) is weighed and added to a 100 mL round-bottom flask, and a mixed solvent of tetrahydrofuran and toluene (V1:V2 = 3:1) is added to dissolve. Ethyl glyoxylate (0.918 g, 4.5 mmol) containing 50% toluene is then added to the flask, N2 protection is introduced, and then the mixture is transferred to a 60°C oil bath for reaction for 4 hours. After the reaction is completed, the mixture is cooled, desolventized, and separated by column chromatography to obtain an N-arylquinazolin-thioimidazole compound having the general structural formula (I).

[0030] Preferably, the solvent is an organic solvent, preferably a mixed solvent of tetrahydrofuran and toluene (V1:V2=3:1).

[0031] Preferably, the molar ratio of ethyl glyoxylate to the key reactant (such as compound II-1) is 1.1:1, preferably 1.2-2:1, and more preferably 1.2-1.5:1.

[0032] Preferably, the reaction solvent has different preferences in different steps. For the synthesis step of compound I, a mixture of tetrahydrofuran and toluene is used as the solvent; for the synthesis step of compound II, dichloromethane is used as the solvent.

[0033] In another aspect, the present invention provides an N-arylquinazolinothioimidazolinone compound having the general structural formula (Ⅰ), or the use of the N-arylquinazolinothioimidazolinone compound having the general structural formula (Ⅰ) prepared by the above method, wherein the N-arylquinazolinothioimidazolinone compound having the general structural formula (Ⅰ) is used for inhibiting fungi on crops; specifically, it is used for inhibiting one or more of Gibberella fusca, Rice blast, Phytophthora sclerotiorum, Sclerotinia sclerotiorum, Botrytis cinerea, and Sheath blight.

[0034] Preferably, the N-arylquinazolinone compound having the general structural formula (I) is used to inhibit Sclerotinia sclerotiorum.

[0035] Another aspect of the present invention provides an N-arylquinazolin-thioimidazolinone compound having the general structural formula (Ⅰ), or the use of the N-arylquinazolin-thioimidazolinone compound having the general structural formula (Ⅰ) prepared by the above method, wherein the N-arylquinazolin-thioimidazolinone compound having the general structural formula (Ⅰ) is used to prepare a drug for inhibiting fungi in crops, specifically for preparing a drug for inhibiting one or more pathogens selected from the group consisting of ergot, rice blast, phytophthora, sclerotinia, gray mold and sheath blight.

[0036] Preferably, the N-arylquinazolinone thioimidazole compound having the general structural formula (I) is used as a drug for inhibiting rice blast fungus, sclerotinia sclerotiorum and sheath blight fungus.

[0037] After adopting the above technical solution, the present invention has the following beneficial effects compared with the prior art.

[0038] The compound described in this invention is prepared from 2-aminobenzylamine and phenyl isothiocyanate compounds. They react in dichloromethane with triethylamine to produce a 1-(2-aminobenzyl)-3-phenylthiourea compound. This 1-(2-aminobenzyl)-3-phenylthiourea compound is then reacted with ethyl glyoxylate to yield an N-arylquinazolinothioimidazolinone compound. This compound is simple to prepare, uses readily available raw materials, and exhibits excellent antibacterial activity against crop pathogens, particularly fusarium head blight, phytophthora, rice blast, sclerotinia sclerotiorum, gray mold, and sheath blight, effectively ensuring crop yields.

[0039] The specific embodiments of the present invention will be described in further detail below with reference to the accompanying drawings. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] The accompanying drawings are part of this application and are used to provide a further understanding of the present invention. The exemplary embodiments of the present invention and their descriptions are used to explain the present invention, but do not constitute an undue limitation of the present invention. Obviously, the drawings described below are only some embodiments. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without inventive effort. In the accompanying drawings:

[0041] Figure 1 The figure is a structural diagram of the N-arylquinazoline-thioimidazolone compound having the general structural formula (I) of the present invention.

[0042] Figure 2The synthetic route diagram of the N-arylquinazoline-thioimidazolone compound having the general structural formula (I) of the present invention is shown.

[0043] It should be noted that these drawings and textual descriptions are not intended to limit the conceptual scope of the present invention in any way, but rather to illustrate the concept of the present invention for those skilled in the art by referring to specific embodiments. DETAILED DESCRIPTION

[0044] To make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the following will be combined with the appended drawings of the embodiments of the present invention. Figure 1-2 , the technical solutions in the embodiments are described clearly and completely. The following embodiments are used to illustrate the present invention but are not used to limit the scope of the present invention.

[0045] The structural formula of the intermediate product of the present invention is as follows:

[0046] Table 1 Structural formula of intermediate products

[0047]

[0048] The sources of the chemical reagents used in the embodiments of the present invention are as follows:

[0049] Shanghai Myrel Chemical Technology Co., Ltd.: 2-aminobenzylamine (CAS: 4403-69-4), phenyl isothiocyanate (CAS: 103-72-0), 4-toluene isothiocyanate (CAS: 622-59-3), 2-toluene isothiocyanate (CAS: 614-69-7), 4-n-butylphenyl isothiocyanate (CAS: 23165-44-8), dichloromethane (CAS: 75-09-2).

[0050] Xilong Chemical Co., Ltd.: triethylamine (CAS: 121-44-8).

[0051] Guangdong Guanghua Science and Technology Co., Ltd.: tetrahydrofuran (CAS: 109-99-9), ethyl acetate (CAS: 141-78-6).

[0052] Anhui Zesheng Technology Co., Ltd.: Ethyl glyoxylate (CAS: 924-44-7).

[0053] Sinopharm Chemical Reagent Co., Ltd.: Toluene (CAS: 108-88-3).

[0054] Example A1

[0055] Synthesis of N-phenylquinazolin-thioimidazolinone:

[0056]

[0057] 2-Aminobenzylamine (1.221 g, 10 mmol), phenyl isothiocyanate (1.487 g, 11 mmol), and triethylamine (1.012 g, 10 mmol) were weighed into a 100 mL round-bottom flask, and 45 mL of dichloromethane was added to dissolve the mixture. The reaction solution was reacted at room temperature. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography to obtain 1-(2-aminobenzyl)-3-phenylthiourea as a white solid.

[0058] 1-(2-Aminobenzyl)-3-phenylthiourea (0.772 g, 3 mmol) was weighed and added to a 100 mL round-bottom flask. A mixture of tetrahydrofuran and toluene (V1:V2 = 3:1) was added to dissolve the mixture. Ethyl glyoxylate (0.918 g, 4.5 mmol) containing 50% toluene was then added to the flask. N2 was introduced for protection, and the mixture was transferred to a 60°C oil bath for 4 h. After completion of the reaction, the mixture was cooled, desolvated under reduced pressure, and separated by column chromatography to yield a yellow solid. Melting point (mp): 218.3°C–219.2°C.

[0059] 1 HNMR (400MHz, DMSO-d6) δ7.58-7.43(m,3H),7.35(d,J=7.1Hz,2H),7.18(d,J=7.6Hz,1H),7.10(t,J=7.6Hz,1H),7.02(s, 1H), 6.91 (d, J = 7.9Hz, 1H), 6.82 (t, J = 7.4Hz, 1H), 5.41 (d, J = 1.5Hz, 1H), 5.31 (d, J = 17.0Hz, 1H), 4.70 (d, J = 17.0Hz, 1H).

[0060] 13 CNMR(101MHz,DMSO-d6)δ180.20,170.28,141.65,133.14,128.95,128.72,127.57,126.90,119.44,117.58,116.80,65.59,44.00.

[0061] Example A2

[0062] Synthesis of N-(4-methylphenyl)quinazolin-thioimidazolinone:

[0063]

[0064] 2-Aminobenzylamine (1.221 g, 10 mmol), 4-tolyl isothiocyanate (1.641 g, 11 mmol), and triethylamine (1.012 g, 10 mmol) were weighed into a 100 mL round-bottom flask, and 45 mL of dichloromethane was added to dissolve the mixture. The reaction solution was reacted at room temperature. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography to obtain 1-(2-aminobenzyl)-3-(4-methylphenyl)thiourea as a white solid.

[0065] 1-(2-Aminobenzyl)-3-(4-methylphenyl)thiourea (0.814 g, 3 mmol) was weighed and added to a 100 mL round-bottom flask. A mixture of tetrahydrofuran and toluene (V1:V2 = 3:1) was added to dissolve the mixture. Ethyl glyoxylate (0.918 g, 4.5 mmol) containing 50% toluene was then added to the flask. N2 was introduced for protection, and the mixture was transferred to a 60°C oil bath for 4 h. After the reaction, the mixture was cooled, desolvated under reduced pressure, and separated by column chromatography to yield a yellow solid. Melting point (mp): 244.5°C-245.9°C.

[0066] 1 HNMR (400MHz, DMSO-d6) δ7.31(d,J=8.2Hz,2H),7.21(d,J=8.3Hz,2H),7.18(d,J=7.6Hz,1H),7.10(t,J=7.6Hz,1H),6.96(d,J=30.5Hz ,1H),6.90(d,J=7.8Hz,1H),6.81(t,J=7.4Hz,1H),5.39(s,1H),5.30(d,J=17.0Hz,1H),4.68(d,J=17.0Hz,1H),2.37(d,J=5.0Hz,3H).

[0067] 13 CNMR(101MHz,DMSO-d6)δ180.39,170.32,141.65,138.51,130.52,129.42,128.41,127.54,126.87,119.40,117.58,116.77,65.53,43.99,20.75.

[0068] Example A3

[0069] Synthesis of N-(3-methylphenyl)quinazolin-thioimidazolinone:

[0070]

[0071] 2-Aminobenzylamine (1.221 g, 10 mmol), 3-tolyl isothiocyanate (1.641 g, 11 mmol), and triethylamine (1.012 g, 10 mmol) were weighed into a 100 mL round-bottom flask, and 45 mL of dichloromethane was added to dissolve the mixture. The reaction solution was reacted at room temperature. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography to obtain 1-(2-aminobenzyl)-3-(3-methylphenyl)thiourea as a white solid.

[0072] 1-(2-Aminobenzyl)-3-(3-methylphenyl)thiourea (0.814 g, 3 mmol) was weighed and added to a 100 mL round-bottom flask. A mixture of tetrahydrofuran and toluene (V1:V2 = 3:1) was added to dissolve the mixture. Ethyl glyoxylate (0.918 g, 4.5 mmol) containing 50% toluene was then added to the flask. N2 was introduced for protection, and the mixture was transferred to a 60°C oil bath for 4 h. After the reaction, the mixture was cooled, desolvated under reduced pressure, and separated by column chromatography to yield a yellow solid. Melting point (mp): 185.3°C–186.7°C.

[0073] 1 H NMR (400MHz, DMSO-d6) δ7.40(t,J=7.7Hz,1H),7.29(d,J=7.6Hz,1H),7.21-7.07(m,4H),7.01(s,1H),6.91(d,J=7.6Hz ,1H),6.82(td,J=7.6,1.0Hz,1H),5.40(s,1H),5.31(d,J=17.0Hz,1H),4.69(d,J=17.0Hz,1H),2.36(d,J=5.7Hz,3H).

[0074] 13 CNMR(101MHz,DMSO-d6)δ180.79,170.78,142.16,138.96,133.57,130.09,129.5 4,129.25,128.06,127.38,126.28,119.92,118.09,117.28,66.07,44.49,21.24.

[0075] Example A4

[0076] Synthesis of N-(4-n-butylphenyl)quinazolin-thioimidazolinone:

[0077]

[0078] 2-Aminobenzylamine (1.221 g, 10 mmol), 4-n-butylphenyl isothiocyanate (2.104 g, 11 mmol), and triethylamine (1.012 g, 10 mmol) were weighed into a 100 mL round-bottom flask, and 45 mL of dichloromethane was added to dissolve the mixture. The reaction solution was reacted at room temperature. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography to obtain 1-(2-aminobenzyl)-3-(4-n-butylphenyl)thiourea as a white solid.

[0079] 1-(2-Aminobenzyl)-3-(4-n-butylphenyl)thiourea (0.940 g, 3 mmol) was weighed and added to a 100 mL round-bottom flask. A mixture of tetrahydrofuran and toluene (V1:V2 = 3:1) was added to dissolve the mixture. Ethyl glyoxylate (0.918 g, 4.5 mmol) containing 50% toluene was then added to the flask. N2 was introduced for protection, and the mixture was transferred to a 60°C oil bath for 4 h. After the reaction, the mixture was cooled, desolvated under reduced pressure, and separated by column chromatography to yield a yellow solid. Melting point (mp): 149.9°C–150.8°C.

[0080] 1 HNMR(400MHz,DMSO-d6)δ7.33(q,J=3.8Hz,2H),7.23(d,J=8.3Hz,2H),7.18(d, J=7.6Hz,1H),7.10(t,J=7.6Hz,1H),7.00(s,1H),6.90(d,J=7.8Hz,1H),6.81( t,J=7.4Hz,1H),5.40(s,1H),5.30(d,J=17.0Hz,1H),4.69(d,J=17.1Hz,1H),2 .68-2.60(m,2H),1.68-1.52(m,2H),1.41-1.27(m,2H),0.92(t,J=7.3Hz,3H).

[0081] 13 CNMR(101MHz,DMSO-d6)δ180.36,170.34,143.24,141.65,130.68,128.72,128.40, 127.54,126.86,119.40,117.57,116.76,65.52,43.98,34.45,32.93,21.78,13.74.

[0082] Antibacterial activity test of crops

[0083] The antibacterial activity of N-phenylquinazolin-thioimidazolinone, N-(4-methylphenyl)quinazolin-thioimidazolinone, N-(3-methylphenyl)quinazolin-thioimidazolinone and N-(4-n-butylphenyl)quinazolin-thioimidazolinone was tested in vitro.

[0084] The fungicidal activity of wheat fusarium head blight, pepper blast, rice blast, rapeseed sclerotinia, cucumber gray mold, and rice sheath blight was tested. The test agent was dissolved in acetone and then diluted to a 500 g / mL solution with 200 g / mL Sorporl-144 emulsifier. Under aseptic conditions, 1 mL of the compound solution was pipetted into a sterilized plate. Then, 9 mL of sterilized PDA culture medium was added to the plate and mixed thoroughly to prepare drug-containing plates of the appropriate concentration. A sterile 4 mm diameter borer was used to cut a bacterial cake from the edge of the colony. After the culture solidified, the cake was inoculated into the center of the drug-containing plate using an inoculator and incubated in an incubator at an appropriate temperature. A blank control was used without the addition of the drug. Each treatment was cultured in an incubator at 24±1°C. After 72 hours, the colony diameter was observed and measured. The diameter of each colony was measured vertically once using the cross method, and the average value was taken.

[0085] Growth inhibition rate (%): (control colony diameter - treated colony diameter) × 100 / (control colony diameter - 4 mm).

[0086] The drug concentration was 50 μg / mL. The antibacterial activity test results are shown in Table 2.

[0087] Table 2 Antibacterial activity results

[0088]

[0089] As shown in Table 2, all target compounds exhibited antibacterial activity against the tested pathogens, with some exhibiting significant activity. Among them, N-phenylquinazolin-thioimidazolinone and N-(4-n-butylphenyl)quinazolin-thioimidazolinone exhibited inhibition rates of up to 71.3% against Sclerotinia sclerotiorum; N-(3-methylphenyl)quinazolin-thioimidazolinone exhibited an inhibition rate of up to 68.1% against Sclerotinia sclerotiorum; and N-(4-n-butylphenyl)quinazolin-thioimidazolinone exhibited an inhibition rate of 60.0% against Gibberella graminearum.

[0090] The above description is merely a preferred embodiment of the present invention and does not constitute any form of limitation to the present invention. Although the present invention has been disclosed as above in terms of a preferred embodiment, it is not intended to limit the present invention. Any technician familiar with this patent can make slight changes or modifications to equivalent embodiments using the above technical content without departing from the scope of the technical solution of the present invention. However, any simple modifications, equivalent changes, and modifications made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solution of the present invention are still within the scope of the solution of the present invention.

Claims

1. An N-arylquinazolin-thioimidazolinone compound, characterized in that: The compound has the general structural formula (I), In formula (I), R is H or an alkyl group.

2. The N-arylquinazolinone compound according to claim 1, wherein R is one of H, methyl or butyl.

3. An N-arylquinazolin-thioimidazolinone compound, characterized in that: The compound is selected from one or more of the following compounds: N-phenylquinazolinthioimidazolidinone N-(4-Methylphenyl)quinazolinthioimidazolidinone N-(3-Methylphenyl)quinazolinthioimidazolidinone N-(4-n-Butylphenyl)quinazolinthioimidazolidinone 4. A method for preparing an N-arylquinazolin-thioimidazolinone compound having the general structural formula (I), characterized in that: A thiourea compound having the general structural formula (II) is reacted with ethyl glyoxylate in the absence of a catalyst to prepare an N-arylquinazolinothioimidazolinone compound having the general structural formula (I); In formula (I), R is H or an alkyl group.

5. The preparation method according to claim 4, characterized in that The preparation method specifically comprises the following steps: S1) reacting 2-aminobenzylamine of structural formula (IV) with a phenyl isothiocyanate compound of structural formula (III) in dichloromethane under the action of triethylamine to obtain a thiourea compound of structural formula (II): S2) reacting a thiourea compound having the general structural formula (II) with ethyl glyoxylate to prepare an N-arylquinazolin-thioimidazolone compound having the general structural formula (I): In formula (I), R is H or an alkyl group.

6. The preparation method according to claim 5, characterized in that R is one of H, methyl or butyl.

7. The preparation method according to claim 5, characterized in that Step S1) is specifically as follows: 2-aminobenzylamine of the general formula (IV), an aryl isothiocyanate of the general formula (III), and triethylamine are weighed and added to a 100 mL round-bottom flask, 45 mL of dichloromethane is added to dissolve them, and the reaction solution is reacted at room temperature. After the reaction is completed, the solvent is removed under reduced pressure, and the thiourea compound (II) is separated by column chromatography; Step S2) is specifically as follows: compound II is weighed, added to a 100 mL round-bottom flask, and dissolved in a mixed solvent of tetrahydrofuran and toluene, and then ethyl glyoxylate containing 50% toluene is added to the flask, N2 protection is introduced, and then transferred to a 60 ° C oil bath for reaction for 4 hours. After the reaction is completed, it is cooled, desolvated under reduced pressure, and separated by column chromatography to obtain an N-arylquinazoline and thioimidazole ketone compound having the general structural formula (Ⅰ).

8. The preparation method according to claim 7, characterized in that In step S1), 2-aminobenzylamine having the general structural formula (IV), aryl isothiocyanate having the general structural formula (III), and triethylamine are added in a molar ratio of 1:1.1:1, and the reaction time is 4 hours. In step S2), tetrahydrofuran and toluene are mixed in a volume ratio of 3:1, and the molar ratio of ethyl glyoxylate to compound II is 1.1:

1.

9. Use of an N-arylquinazolin-thioimidazolinone compound having the general structural formula (I) according to any one of claims 1 to 3 or an N-arylquinazolin-thioimidazolinone compound having the general structural formula (I) prepared by the method according to any one of claims 4 to 8, characterized in that: Used for antibacterial treatment of crops, or for preparing drugs for antibacterial treatment of crops.

10. The use according to claim 9, characterized in that Used for inhibiting fungi in crops, including inhibiting one or more of Gibberella, Rice Blast, Phytophthora, Sclerotinia, Botrytis Cinerea and Sheath Blight; The drug used for preparing antibacterial drugs for crops includes drugs used for preparing drugs for inhibiting one or more pathogens selected from the group consisting of fusarium head blight, rice blast, phytophthora, sclerotinia, gray mold and sheath blight.

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