1-arylmethyl-3-aryl tetrahydropyrimidine-2 (1H)-ketone compound as well as preparation method and application thereof

Abstract

The invention discloses a 1-arylmethyl-3-aryl tetrahydropyrimidine-2 (1H)-ketone compound as well as a preparation method and application thereof, the compound has a structure as shown in a general formula (VI), and R1 and R2 are substituent groups such as hydrogen, alkyl, alkoxy, halogen, cyano or tert-butyl. The compounds take CO2 as a carbonyl source, the preparation method is simple, the raw materials are easy to obtain, and the series of tetrahydropyrimidone compounds have a good inhibition effect on the activity of crop germs, particularly have a remarkable inhibition effect on the activity of germs such as phytophthora germs, rhizoctonia solani, valsa ceratosperma and sclerotinia sclerotiorum, and can be used for preparing agricultural antibacterial drugs.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound, its preparation method, and its uses. Background Technology

[0002] Most heterocyclic compounds possess broad and important biological activities, among which nitrogen-containing heterocyclic compounds occupy a central position in medicinal chemistry due to their unique electronic structure and good biocompatibility. Pyrimidine ketones, as a typical class of nitrogen-containing heterocyclic skeletons, are widely found in natural products and clinical drugs, serving as important lead structures in drug discovery and structural modification. They exhibit a variety of biological activities, including antitumor, antiviral, anti-inflammatory, and central nervous system modulation, possessing significant research value and application prospects. Pyrimidine ketones, as an important class of nitrogen-containing heterocyclic structures, are widely found in various bioactive molecules and drug lead compounds, occupying a crucial position in medicinal chemistry. These compounds typically contain multiple nitrogen atoms and amide functional groups, enabling them to form stable hydrogen bonds and other non-covalent interactions with biological targets, thus exhibiting diverse biological activities such as antitumor, anti-inflammatory, antibacterial, and central nervous system modulation, demonstrating excellent research value and application prospects.

[0003] Among pyrimidinone skeletons, tetrahydropyrimidinones, as one of their important saturated derivatives, have attracted widespread attention in drug molecule design due to their higher conformational flexibility and richer three-dimensional structures. Kappe et al. systematically summarized and developed tetrahydropyrimidinone construction strategies represented by the Biginelli reaction, making this type of skeleton one of the classic and easily functionalized heterocyclic structures in medicinal chemistry. Subsequently, Atwal et al.'s research showed that some tetrahydropyrimidinone derivatives have shown potential application value in calcium ion channel regulation-related research, and have attracted continuous attention in the field of cardiovascular disease drug development. In addition, several research teams (such as Baraldi, Zhao, etc.) have also reported the application potential of pyrimidinone and tetrahydropyrimidinone skeletons in enzyme inhibition and tumor-related models. Due to their strong structural tunability and rich substitution modes, pyrimidinones and tetrahydropyrimidinone compounds have gradually developed into important and advantageous skeletons for constructing bioactive molecules.

[0004] Currently, the synthesis cost of pyrimidine ketones is generally high according to publicly available information, which poses a significant obstacle to the widespread application of drugs. From the perspectives of economy, greenness, and environmental protection, we designed and synthesized 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketones by using readily available carbon dioxide as the carbonyl source, and studied the antibacterial activity of these compounds. Summary of the Invention

[0005] The technical problem to be solved by the present invention is to overcome the shortcomings of the prior art and provide a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound, its preparation method and uses. The compound uses CO2 as a carbonyl source, the preparation method is simple and the raw materials are readily available. At the same time, it has a good inhibitory effect on the activity of crop pathogens, especially on pathogens such as Phytophthora, Rhizoctonia solani, Pseudomonas rotundus and Sclerotinia sclerotiorum.

[0006] To solve the above-mentioned technical problems, the basic concept of the technical solution adopted by the present invention is as follows:

[0007] In one aspect, this invention provides a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketone compound having the general structural formula (VI).

[0008] ;

[0009] (VI)

[0010] In formula (VI), R1 is hydrogen, C1-C3 alkyl, C1-C2 alkoxy, halogen, cyano or tert-butyl; R2 is hydrogen, C1-C3 alkyl or C1-C2 alkoxy.

[0011] Preferably, R1 is H, 4-CH3O, 4-CH3, 4-Cl, 4-F, 4-C(CH3)3, 4-CN, 3-CH3, 3-CH3O, 3-Cl, 2-CH3, or 2-Cl; R2 is 4-CH3O, 4-CH3, 4-Cl, 3-CH3, 3-Cl, 2-CH3, or 2-Cl.

[0012] Preferably, the 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketone compound having the general structural formula (VI) is specifically selected from one or more of the following compounds:

[0013] 1-Benzyl-3-phenyltetrahydropyrimidine-2(1H)-one:

[0014] ;

[0015] 1-(4-Methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0016] ;

[0017] 1-(4-Methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0018] ;

[0019] 1-(4-fluorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0020] ;

[0021] 1-(4-Chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0022] ;

[0023] 1-(4-tert-butylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0024] ;

[0025] 1-(4-cyanophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0026] ;

[0027] 1-(3-Methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0028] ;

[0029] 1-(3-Methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0030] ;

[0031] 1-(3-Chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0032] ;

[0033] 1-(2-Methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0034] ;

[0035] 1-(2-Chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one:

[0036] ;

[0037] 1-Benzyl-3-(4-methoxyphenyl)tetrahydropyrimidine-2(1H)-one:

[0038] ;

[0039] 1-Benzyl-3-(4-methylphenyl)tetrahydropyrimidine-2(1H)-one:

[0040] ;

[0041] 1-Benzyl-3-(4-chlorophenyl)tetrahydropyrimidine-2(1H)-one:

[0042] ;

[0043] 1-Benzyl-3-(3-Tolyl)tetrahydropyrimidine-2(1H)-one:

[0044] ;

[0045] 1-Benzyl-3-(3-chlorophenyl)tetrahydropyrimidine-2(1H)-one:

[0046] ;

[0047] 1-Benzyl-3-(2-Tolyl)tetrahydropyrimidine-2(1H)-one:

[0048] ;

[0049] 1-Benzyl-3-(2-chlorophenyl)tetrahydropyrimidine-2(1H)-one:

[0050] .

[0051] Another aspect of the present invention provides a method for synthesizing 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compounds having the general structural formula (VI), the method specifically comprising the following steps:

[0052] S1) An aryl iodide of structural formula (I) and 1,3-propanediamine of structural formula (II) are coupled via a Ullmann coupling reaction using KOH as a base and CuCl as a catalyst to obtain an N-aryl-1,3-propanediamine compound of structural formula (III). Finally, the N-aryl-1,3-propanediamine compound of structural formula (III) is N-alkylated with aryl methyl chloride of structural formula (IV) in acetonitrile solvent using K2CO3 as a base to obtain an N-arylmethyl-N'-arylpropanediamine compound of structural formula (V).

[0053] ;

[0054] S2) Under alkaline conditions, N-arylmethyl-N'-arylpropanediamine compounds with general structural formula (V) were mixed with CO2 in an organic solvent system to obtain 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketone compounds with general structural formula (VI) in the presence of p-toluenesulfonyl chloride.

[0055] ;

[0056] In the formula, R1 is hydrogen, C1-C3 alkyl, C1-C2 alkoxy, halogen, cyano or tert-butyl; R2 is hydrogen, C1-C3 alkyl or C1-C2 alkoxy.

[0057] Preferably, R1 is H, 4-CH3O, 4-CH3, 4-Cl, 4-F, 4-C(CH3)3, 4-CN, 3-CH3, 3-CH3O, 3-Cl, 2-CH3, or 2-Cl; R2 is 4-CH3O, 4-CH3, 4-Cl, 3-CH3, 3-Cl, 2-CH3, or 2-Cl.

[0058] Preferably, step S1) specifically involves: aryl iodide of structural formula (I) and 1,3-propanediamine of structural formula (II) undergoing a Ullmann coupling reaction with KOH as a base and CuCl as a catalyst to obtain N-aryl-1,3-propanediamine compounds of structural formula (III); finally, N-aryl-1,3-propanediamine compounds of structural formula (III) are N-alkylated with aryl methyl chloride of structural formula (IV) in acetonitrile solvent with K2CO3 as a base to obtain N-arylmethyl-N'-arylpropanediamine compounds of structural formula (V).

[0059] In this invention, in step S1), the molar ratio of the aryl iodide having general structural formula (I), 1,3-propanediamine having structural formula (II), KOH, and CuCl added to the reaction is 1:2-3:1-2:0.1-0.3, preferably 1:3:0.1. The molar ratio of the N-aryl-1,3-propanediamine compound having structural formula (III) to the aryl methyl chloride having structural formula (IV) and K2CO3 added to the reaction is 1:1-1.2:1.5-2, preferably 1:1.2:2. The reaction temperature is 0 to 30°C, preferably 20 to 25°C. The reaction time is 2 to 24 h, preferably 2 to 5 h.

[0060] Preferably, step S2) specifically involves: adding an N-arylmethyl-N'-arylpropanediamine compound with structural formula (V) to an organic solvent, then adding a base, introducing CO2 gas and stirring the system for a certain period of time, finally adding p-toluenesulfonyl chloride to the mixture, reacting, separating, and obtaining a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketone compound with general structural formula (VI).

[0061] Preferably, step S2) specifically involves: dissolving an N-arylmethyl-N'-arylpropanediamine compound having the general structural formula (V) in acetonitrile at room temperature; adding 1,8-diazabicyclo[5.4.0]undec-7-ene; continuously bubbling CO2 gas into the mixture; and finally adding p-toluenesulfonyl chloride and reacting for 30 minutes to obtain a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound having the general structural formula (VI). After the reaction is complete, the mixture is quenched with a saturated sodium bicarbonate aqueous solution, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over anhydrous Na2SO4 and dissolved under reduced pressure. The product is obtained by column chromatography.

[0062] Preferably, the base is triethylamine, triethylenediamine, 1,8-diazabicyclo[5.4.0]undec-7-ene or 4-dimethylaminopyridine, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0063] Preferably, the organic solvent is dichloromethane, N,N-dimethylformamide, toluene, dimethyl sulfoxide, or acetonitrile, with acetonitrile being the preferred choice.

[0064] In this invention, in step S2), the molar ratio of the N-arylmethyl-N'-arylpropanediamine compound having the general structural formula (V) to 1,8-diazabicyclo[5.4.0]undec-7-ene and p-toluenesulfonyl chloride is 1:1.5-2.0:1.0-1.5, preferably 1:1.5-2.0:1.0-1.4, and more preferably 1:1.9-2.0:1.0-1.2.

[0065] Preferably, the temperature selected for the entire reaction process is 0-35℃, preferably 20-25℃, such as 21℃, 23℃, 25℃.

[0066] Preferably, the reaction time after adding p-toluenesulfonyl chloride to the reaction system is 10-60 min, preferably 30-40 min, such as 30 min, 35 min, or 40 min.

[0067] In this invention, the separation is performed by filtration, vacuum filtration, or extraction; preferably, brine is used for extraction and separation.

[0068] Preferably, the present invention further includes drying the extracted organic phase, preferably using anhydrous Na2SO4.

[0069] Preferably, the present invention further includes a solvent removal process for the dried product, preferably using vacuum desolventizing.

[0070] In another aspect, the present invention provides the use of a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound having the general structural formula (VI), or a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound having the general structural formula (VI) prepared by the above method, wherein the 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound having the general structural formula (VI) is used to prepare antibacterial drugs; specifically, it is used to prepare drugs that inhibit one or more of the following pathogens: Phytophthora, Rhizoctonia solani, Pseudomonas rotundifolia, and Sclerotinia sclerotiorum.

[0071] Preferably, the 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound having the general structural formula (VI) is used to prepare a drug for inhibiting Phytophthora, Rhizoctonia solani, Pseudomonas rotundifolia and Sclerotinia sclerotiorum.

[0072] By adopting the above technical solution, the present invention has the following beneficial effects compared with the prior art.

[0073] This invention provides a method for preparing a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound for antibacterial purposes using CO2 as a carbonyl source. The preparation method of this compound is simple, the raw materials are readily available, and it has good inhibitory activity against cancer cells, especially against Phytophthora, Rhizoctonia solani, Pseudomonas spp. and Sclerotinia spp.

[0074] The specific embodiments of the present invention will now be described in further detail with reference to the accompanying drawings. Attached Figure Description

[0075] The accompanying drawings, which form part of this application, are used to provide a further understanding of the invention. The illustrative embodiments and descriptions of the invention are used to explain the invention, but do not constitute an undue limitation of the invention. Obviously, the drawings described below are merely some embodiments, and those skilled in the art can obtain other drawings based on these drawings without creative effort. In the drawings:

[0076] Figure 1 This is a structural diagram of a 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketone compound having the general structural formula (VI) described in this invention.

[0077] Figure 2 This is a synthetic circuit diagram of the 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-one compound having the general structural formula (VI) of the present invention.

[0078] It should be noted that these accompanying drawings and textual descriptions are not intended to limit the scope of the invention in any way, but rather to illustrate the concept of the invention to those skilled in the art by referring to specific embodiments. Detailed Implementation

[0079] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments will be clearly and completely described below with reference to the accompanying drawings. The following embodiments are used to illustrate the present invention, but are not intended to limit the scope of the present invention.

[0080] The sources of the chemical reagents used in the various embodiments of this invention are shown in Table 1 below:

[0081] Table 1 Sources of Chemical Reagents

[0082] reagents Structure or source Anhydrous potassium carbonate (CAS: 584-08-7) Shanghai Myriel Chemical Technology Co., Ltd. Acetonitrile (CAS: 75-05-8) Xilong Chemical Co., Ltd. 1,8-Diazabicyclo[5.4.0]undec-7-ene (CAS: 6674-22-2) Shanghai Myriel Chemical Technology Co., Ltd. Potassium hydroxide (CAS: 1310-58-3) Shanghai Myriel Chemical Technology Co., Ltd. Cuprous chloride (CAS: 7758-89-6) Shanghai Myriel Chemical Technology Co., Ltd. p-Toluenesulfonyl chloride (CAS: 98-59-9) Shanghai Myriel Chemical Technology Co., Ltd. Benzyl chloride (CAS: 100-44-7) Shanghai Myriel Chemical Technology Co., Ltd. p-Methoxybenzyl chloride (CAS: 824-94-2) Shanghai Myriel Chemical Technology Co., Ltd. p-Methylbenzyl chloride (CAS: 104-82-5) Shanghai Myriel Chemical Technology Co., Ltd. Parafluorobenzyl chloride (CAS: 352-11-4) Shanghai Myriel Chemical Technology Co., Ltd. p-chlorobenzyl chloride (CAS: 104-83-6) Shanghai Myriel Chemical Technology Co., Ltd. p-tert-butylbenzyl chloride (CAS: 19692-45-6) Shanghai Myriel Chemical Technology Co., Ltd. p-Cyanobenzyl chloride (CAS: 874-86-2) Shanghai Myriel Chemical Technology Co., Ltd. m-Methoxybenzyl chloride (CAS: 824-98-6) Shanghai Myriel Chemical Technology Co., Ltd. m-Methylbenzyl chloride (CAS: 620-19-9) Shanghai Myriel Chemical Technology Co., Ltd. m-Chlorobenzyl chloride (CAS: 620-20-2) Shanghai Myriel Chemical Technology Co., Ltd. o-methylbenzyl chloride (CAS: 552-45-4) Shanghai Myriel Chemical Technology Co., Ltd. o-chlorobenzyl chloride (CAS: 611-19-8) Shanghai Myriel Chemical Technology Co., Ltd. p-Methoxyiodobenzene (CAS: 696-62-8) Shanghai Myriel Chemical Technology Co., Ltd. p-Methyliodobenzene (CAS: 624-31-7) Shanghai Myriel Chemical Technology Co., Ltd. p-Chloroiodobenzene (CAS: 637-87-6) Shanghai Myriel Chemical Technology Co., Ltd. m-Methyliodobenzene (CAS: 625-95-6) Shanghai Myriel Chemical Technology Co., Ltd. m-Chloroiodobenzene (CAS: 625-99-0) Shanghai Myriel Chemical Technology Co., Ltd. 2-Methyliodobenzene (CAS: 615-37-2) Shanghai Myriel Chemical Technology Co., Ltd. o-chloroiodobenzene (CAS: 615-41-8) Shanghai Myriel Chemical Technology Co., Ltd.

[0083] Example 1

[0084] Synthesis of 1-benzyl-3-phenyltetrahydropyrimidine-2(1H)-one

[0085] ;

[0086] Weigh 0.36 g (1.50 mmol) of N¹-phenylmethyl-N³-phenylpropane-1,3-diamine into a round-bottom flask containing 15 mL of acetonitrile, then add 0.751 g (3.0 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. Continuously purge the mixed solution with CO2, and finally add 0.343 g (1.8 mmol) of p-toluenesulfonyl chloride. After reacting for 30 min, filter the solution, remove the solvent from the filtrate under reduced pressure, and separate the residue by column chromatography to obtain an orange-yellow oil with a yield of 92%.

[0087] 1 H NMR (400 MHz, Chloroform-d) δ 7.36 – 7.28 (m, 8H), 7.28 – 7.22 (m,1H), 7.18 – 7.09 (m, 1H), 4.61 (s, 2H), 3.68 (t, J = 6.1 Hz, 2H), 3.28 (t, J = 6.1 Hz, 2H), 2.04 (p, J = 5.9 Hz, 2H).

[0088] 13 C NMR (101 MHz, Chloroform-d) δ 155.31, 144.37, 138.30, 128.60,128.53, 128.13, 127.21, 125.61, 125.12, 51.43, 48.84, 45.47, 22.67.

[0089] Example 2

[0090] Synthesis of 1-(4-methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0091] ;

[0092] According to the process conditions of Example 1, N 1 -(4-Methoxybenzyl)-N 3 -Phenylacetane 0.405 g (1.50 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene 0.752 g (3.0 mmol) and p-toluenesulfonyl chloride 0.343 g (1.8 mmol), yield: 98%, yellowish-white oil.

[0093] 1 H NMR (400 MHz, Chloroform-d) δ 7.37 – 7.24 (m, 6H), 7.18 – 7.11 (m,1H), 6.86 (d, J = 8.6 Hz, 2H), 4.55 (s, 2H), 3.79 (s, 3H), 3.68 (t, J = 6.1Hz, 2H), 3.28 (t, J = 6.1 Hz, 2H), 2.05 (p, J = 5.9 Hz, 2H).

[0094] 13 C NMR (101 MHz, Chloroform-d) δ 158.98, 155.37, 144.49, 130.50,129.62, 128.69, 125.71, 125.20, 113.98, 55.36, 50.92, 48.92, 45.35, 22.79.

[0095] Example 3

[0096] Synthesis of 1-(4-methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0097] ;

[0098] According to the process conditions of Example 1, N 1 -(4-Methylphenylmethyl)-N 30.381 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.751 g (3.0 mmol) and 0.343 g (1.8 mmol) of p-toluenesulfonyl chloride, in a yield of 96%, in a yellow oil.

[0099] 1 H NMR (400 MHz, Chloroform-d) δ 7.35 – 7.28 (m, 4H), 7.25~7.20 (m,2H), 7.16 – 7.10 (m, 3H), 4.57 (s, 2H), 3.67 (t, J = 6.1 Hz, 2H), 3.27 (t, J= 6.1 Hz, 2H), 2.33 (s, 3H), 2.03 (p, J = 6.0 Hz, 2H).

[0100] 13 C NMR (101 MHz, Chloroform-d) δ 155.33, 144.45, 136.85, 135.28,129.22, 128.62, 128.24, 125.64, 125.12, 51.18, 48.86, 45.37, 22.72, 21.15.

[0101] Example 4

[0102] Synthesis of 1-(4-fluorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0103] ;

[0104] According to the process conditions of Example 1, N 1 -(4-Fluorophenylmethyl)-N 3 0.387 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.752 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 91%, in a white oil.

[0105] 1H NMR (400 MHz, Chloroform-d) δ 7.37 – 7.28 (m, 6H), 7.19 – 7.13 (m,1H), 7.05 – 6.98 (m, 2H), 4.58 (s, 2H), 3.70 (t, J = 6.0 Hz, 2H), 3.30 (t, J = 6.0 Hz, 2H), 2.07 (p, J = 5.9 Hz, 2H).

[0106] 13 C NMR (101 MHz, Chloroform-d) δ 163.44, 161.01, 155.34, 144.34,134.17, 134.14, 129.92, 129.84, 128.72, 125.70, 125.32, 115.51, 115.29,50.88, 48.92, 45.56, 22.76.

[0107] Example 5

[0108] Synthesis of 1-(4-chlorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0109] ;

[0110] According to the process conditions of Example 1, N 1 -(4-Chlorophenylmethyl)-N 3 0.413 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.754 g (3.01 mmol) and 0.344 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 91%, in a yellowish-white oil.

[0111] 1 H NMR (400 MHz, Chloroform-d) δ 7.37 – 7.25 (m, 8H), 7.19 – 7.13 (m,1H), 4.57 (s, 2H), 3.70 (t, J = 5.7 Hz, 2H), 3.29 (t, J = 6.1 Hz, 2H), 2.07(p, J = 5.9 Hz, 2H).

[0112] 13C NMR (101 MHz, Chloroform-d) δ 155.33, 144.29, 136.96, 133.08,129.63, 128.73, 125.70, 125.35, 50.97, 48.93, 45.66, 22.76.

[0113] Example 6

[0114] Synthesis of 1-(4-tert-butylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0115] ;

[0116] According to the process conditions of Example 1, N 1 -(4-tert-butylbenzyl)-N 3 0.445 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.753 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 93%, in a pale yellow oil.

[0117] 1 H NMR (400 MHz, Chloroform-d) δ 7.37 – 7.28 (m, 6H), 7.26 (d, J =8.1 Hz, 2H), 7.16 – 7.10 (m, 1H), 4.58 (s, 2H), 3.68 (t, J = 5.8 Hz, 2H), 3.29 (t, J = 6.1 Hz, 2H), 2.04 (p, J = 6.0 Hz, 2H), 1.31 (s, 9H).

[0118] 13 C NMR (101 MHz, Chloroform-d) δ 155.32, 150.08, 144.46, 135.24,128.60, 127.89, 125.62, 125.42, 125.08, 51.12, 48.85, 45.52, 34.50, 31.43,22.72.

[0119] Example 7

[0120] Synthesis of 1-(4-cyanophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0121] ;

[0122] According to the process conditions of Example 1, N 1 -(4-cyanophenylmethyl)-N 3 0.398 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.752 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 73%, white oil.

[0123] 1 H NMR (400 MHz, DMSO-d6) δ 7.81 (d, J = 8.3 Hz, 2H), 7.48 (d, J = 8.3Hz, 2H), 7.34~7.27 (m, 4H), 7.15 – 7.10 (m, 1H), 4.59 (s, 2H), 3.68 (t, J =5.7 Hz, 2H), 3.31 (t, J = 6.0 Hz, 2H), 2.03 (p, J = 5.9 Hz, 2H).

[0124] 13 C NMR (101 MHz, DMSO-d6) δ 154.42, 144.73, 144.45, 132.40, 128.21,128.17, 125.42, 124.55, 118.91, 109.68, 50.53, 48.44, 45.88, 22.24.

[0125] Example 8

[0126] Synthesis of 1-(3-methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0127] ;

[0128] According to the process conditions of Example 1, N 1 -(3-Methoxybenzyl)-N 3 0.405 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.752 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 94%, in a pale yellow oil.

[0129] 1H NMR (400 MHz, Chloroform-d) δ 7.37~7.29 (m, 4H), 7.27 – 7.22 (m,1H), 7.18 – 7.12 (m, 1H), 6.92 (d, J = 7.6 Hz, 1H), 6.89 (t, J = 2.1 Hz, 1H), 6.81 (dd, J = 8.2, 1.8 Hz, 1H), 4.60 (s, 2H), 3.80 (s, 3H), 3.71 (t, J = 6.1Hz, 2H), 3.31 (t, J = 6.1 Hz, 2H), 2.07 (p, J = 5.9 Hz, 2H).

[0130] 13 C NMR (101 MHz, Chloroform-d) δ 159.97, 155.40, 144.47, 140.05,129.61, 128.72, 125.73, 125.27, 120.55, 113.74, 112.74, 55.37, 51.47, 48.97,45.57, 22.81.

[0131] Example 9

[0132] Synthesis of 1-(3-methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0133] ;

[0134] According to the process conditions of Example 1, N 1 -(3-Methylphenylmethyl)-N 3 0.381 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.751 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 93%, white oil.

[0135] 1H NMR (400 MHz, Chloroform-d) δ 7.34~7.28 (m, 4H), 7.20 (t, J = 7.5Hz, 1H), 7.16 – 7.09 (m, 3H), 7.05 (d, J = 7.5 Hz, 1H), 4.56 (s, 2H), 3.64(t, J = 5.8 Hz, 2H), 3.25 (t, J = 6.1 Hz, 2H), 2.33 (s, 3H), 2.00 (p, J = 5.9Hz, 2H).

[0136] 13 C NMR (101 MHz, Chloroform-d) δ 155.16, 144.31, 138.10, 138.00,128.75, 128.44, 128.28, 127.86, 125.47, 125.09, 124.93, 51.24, 48.70, 45.30,22.53, 21.32.

[0137] Example 10

[0138] Synthesis of 1-(3-chlorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0139] ;

[0140] According to the process conditions of Example 1, N 1 -(3-Chlorophenylmethyl)-N 3 0.413 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.754 g (3.00 mmol) and 0.344 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 87%, in a yellow oil.

[0141] 1 H NMR (400 MHz, Chloroform-d) δ 7.38~7.27 (m, 5H), 7.27 – 7.20 (m,3H), 7.16 (t, J = 6.8 Hz, 1H), 4.59 (s, 2H), 3.71 (t, J = 6.1 Hz, 2H), 3.31(t, J = 6.1 Hz, 2H), 2.09 (p, J = 5.9 Hz, 2H).

[0142] 13C NMR (101 MHz, Chloroform-d) δ 155.34, 144.30, 140.58, 134.50,129.95, 128.77, 128.16, 127.53, 126.36, 125.73, 125.40, 51.17, 48.97, 45.80,22.79.

[0143] Example 11

[0144] Synthesis of 1-(2-methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0145] ;

[0146] According to the process conditions of Example 1, N 1 -(2-Methylphenylmethyl)-N 3 0.381 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.751 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 82%, white oil.

[0147] 1 H NMR (400 MHz, Chloroform-d) δ 7.36~7.28 (m, 4H), 7.25 – 7.20 (m,1H), 7.20 – 7.12 (m, 4H), 4.66 (s, 2H), 3.71 (t, J = 5.8 Hz, 2H), 3.23 (t, J= 6.1 Hz, 2H), 2.33 (s, 3H), 2.07 (p, J = 6.0 Hz, 2H).

[0148] 13 C NMR (101 MHz, Chloroform-d) δ 155.24, 144.47, 136.74, 135.81,130.53, 128.68, 128.26, 127.28, 126.06, 125.70, 125.22, 49.26, 48.91, 45.37,22.77, 19.29.

[0149] Example 12

[0150] Synthesis of 1-(2-chlorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one

[0151] ;

[0152] According to the process conditions of Example 1, N 1 -(2-Chlorophenylmethyl)-N 3 0.413 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.754 g (3.00 mmol) and 0.344 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 78%, in an orange-yellow oil.

[0153] 1 H NMR (400 MHz, Chloroform-d) δ 7.41 (d, J = 6.7 Hz, 1H), 7.36~7.27(m, 5H), 7.24 (t, J = 7.4 Hz, 1H), 7.19 (d, J = 8.1 Hz, 1H), 7.17 – 7.10 (m,1H), 4.75 (s, 2H), 3.71 (t, J = 5.7 Hz, 2H), 3.35 (t, J = 6.1 Hz, 2H), 2.09(p, J = 5.9 Hz, 2H).

[0154] 13 C NMR (101 MHz, Chloroform-d) δ 155.34, 144.27, 135.68, 133.52,129.44, 129.34, 128.63, 128.37, 127.14, 125.60, 125.20, 48.88, 48.78, 46.13,22.77.

[0155] Example 13

[0156] Synthesis of 1-benzyl-3-(4-methoxyphenyl)tetrahydropyrimidine-2(1H)-one

[0157] ;

[0158] According to the process conditions of Example 1, N 1 -benzyl-N 3 -(4-methoxyphenyl)propane-1,3-diamine 0.405 g (1.50 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene 0.752 g (3.00 mmol) and p-toluenesulfonyl chloride 0.343 g (1.80 mmol), yield: 98%, yellow oil.

[0159] 1 H NMR (400 MHz, Chloroform-d) δ 7.35~7.29 (m, 4H), 7.28~7.24 (m,1H), 7.22 (d, J = 8.9 Hz, 2H), 6.87 (d, J = 8.9 Hz, 2H), 4.61 (s, 2H), 3.78(s, 3H), 3.64 (t, J = 5.8 Hz, 2H), 3.28 (t, J = 6.0 Hz, 2H), 2.04 (p, J = 5.9Hz, 2H).

[0160] 13 C NMR (101 MHz, Chloroform-d) δ 157.24, 155.69, 138.45, 137.53,128.54, 128.20, 127.22, 114.05, 55.54, 51.46, 49.39, 45.49, 22.76.

[0161] Example 14

[0162] Synthesis of 1-benzyl-3-(4-methylphenyl)tetrahydropyrimidine-2(1H)-one

[0163] ;

[0164] According to the process conditions of Example 1, N 1 -benzyl-N 3 0.381 g (1.50 mmol) of (4-methylphenyl)propane-1,3-diamine, 0.751 g (3.00 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 96%, in a yellow oil.

[0165] 1 H NMR (400 MHz, Chloroform-d) δ 7.34 – 7.28 (m, 4H), 7.27 – 7.21 (m,1H), 7.18 (d, J = 8.4 Hz, 2H), 7.12 (d, J = 8.3 Hz, 2H), 4.60 (s, 2H), 3.63(t, J = 6.0 Hz, 2H), 3.26 (t, J = 6.0 Hz, 2H), 2.30 (s, 3H), 2.02 (p, J = 5.9Hz, 2H).

[0166] 13 C NMR (101 MHz, Chloroform-d) δ 155.41, 141.83, 138.36, 134.78,129.20, 128.45, 128.09, 127.12, 125.56, 51.37, 48.99, 45.41, 22.65, 20.90.

[0167] Example 15

[0168] Synthesis of 1-benzyl-3-(4-chlorophenyl)tetrahydropyrimidine-2(1H)-one

[0169] ;

[0170] According to the process conditions of Example 1, N 1 -benzyl-N 3 0.413 g (1.50 mmol) of (4-chlorophenyl)propane-1,3-diamine, 0.754 g (3.00 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 0.344 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 93%, in a yellowish-white oil.

[0171] 1 H NMR (400 MHz, Chloroform-d) δ 7.36~7.31 (m, 4H), 7.30 – 7.23 (m,5H), 4.61 (s, 2H), 3.71 – 3.67 (t, J = 6.0 Hz, 2H), 3.30 (t, J = 6.0 Hz, 2H),2.06 (p, J = 5.9 Hz, 2H).

[0172] 13 C NMR (101 MHz, Chloroform-d) δ 155.18, 142.96, 138.17, 130.43,128.70, 128.66, 128.21, 127.39, 126.82, 51.59, 48.81, 45.56, 22.71.

[0173] Example 16

[0174] Synthesis of 1-benzyl-3-(3-tolyl)tetrahydropyrimidine-2(1H)-one

[0175] ;

[0176] According to the process conditions of Example 1, N 1 -benzyl-N 3 0.381 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.751 g (3.00 mmol) and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 91%, in a yellow oil.

[0177] 1 H NMR (400 MHz, Chloroform-d) δ 7.35 – 7.29 (m, 4H), 7.27 – 7.22 (m,1H), 7.20 (d, J = 7.7 Hz, 1H), 7.14 (s, 1H), 7.08 (dd, J = 8.4, 2.0 Hz, 1H), 6.96 (d, J = 7.5 Hz, 1H), 4.61 (s, 2H), 3.66 (t, J = 6.1 Hz, 2H), 3.27 (t, J= 6.1 Hz, 2H), 2.34 (s, 3H), 2.03 (p, J = 6.0 Hz, 2H).

[0178] 13 C NMR (101 MHz, Chloroform-d) δ 155.37, 144.31, 138.39, 138.35,128.51, 128.48, 128.13, 127.18, 126.59, 126.08, 122.65, 51.41, 48.97, 45.46,22.70, 21.40.

[0179] Example 17

[0180] Synthesis of 1-benzyl-3-(3-chlorophenyl)tetrahydropyrimidine-2(1H)-one

[0181] ;

[0182] According to the process conditions of Example 1, N 1 -benzyl-N 3 0.413 g (1.50 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, 0.754 g (3.00 mmol) and 0.344 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 88%, in a yellow oil.

[0183] 1 H NMR (400 MHz, Chloroform-d) δ 7.34 (s, 1H), 7.33~7.28 (m, 4H), 7.28 – 7.18 (m, 3H), 7.10 (dt, J = 7.0, 2.1 Hz, 1H), 4.60 (s, 2H), 3.65 (t, J= 5.2 Hz, 2H), 3.28 (t, J = 6.1 Hz, 2H), 2.04 (q, J = 5.8, 5.3 Hz, 2H).

[0184] 13 C NMR (101 MHz, Chloroform-d) δ 154.89, 145.43, 137.99, 133.85,129.40, 128.55, 128.05, 127.28, 125.58, 124.97, 123.49, 51.45, 48.58, 45.42,22.53.

[0185] Example 18

[0186] Synthesis of 1-benzyl-3-(2-tolyl)tetrahydropyrimidine-2(1H)-one

[0187] ;

[0188] According to the process conditions of Example 1, N 1 -benzyl-N 3 0.381 g (1.50 mmol) of (2-methylphenyl)propane-1,3-diamine, 0.751 g (3.00 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 0.343 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 68%, in a pale yellow oil.

[0189] 1 H NMR (400 MHz, Chloroform-d) δ 7.33 (d, J = 4.4 Hz, 4H), 7.29 –7.21 (m, 2H), 7.21 – 7.14 (m, 3H), 4.76 (d, J = 15.0 Hz, 1H), 4.46 (d, J =15.0 Hz, 1H), 3.68~3.56 (m, 1H), 3.48~3.39 (m, 1H), 3.36~3.24 (m, 2H), 2.28(s, 3H), 2.10~2.01 (m, 2H).

[0190] 13 C NMR (101 MHz, Chloroform-d) δ 155.13, 143.06, 138.56, 136.07,130.89, 128.55, 128.12, 127.82, 127.21, 127.12, 126.93, 51.31, 49.15, 45.40,22.88, 17.90.

[0191] Example 19

[0192] Synthesis of 1-benzyl-3-(2-chlorophenyl)tetrahydropyrimidine-2(1H)-one

[0193] ;

[0194] According to the process conditions of Example 1, N 1 -benzyl-N 3 0.413 g (1.50 mmol) of (2-chlorophenyl)propane-1,3-diamine, 0.754 g (3.00 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 0.344 g (1.80 mmol) of p-toluenesulfonyl chloride, in a yield of 57%, in a pale yellow oil.

[0195] 1 H NMR (400 MHz, Chloroform-d) δ 7.44 (dd, J = 7.9, 1.6 Hz, 1H), 7.36– 7.32 (m, 4H), 7.31 – 7.23 (m, 2H), 7.21 (td, J = 7.6, 1.8 Hz, 1H), 4.76 (d,J = 14.9 Hz, 1H), 4.47 (d, J = 15.0 Hz, 1H), 3.65 – 3.46 (m, 2H), 3.30 (t, J= 6.0 Hz, 2H), 2.18~1.98 (m, 2H).

[0196] 13 C NMR (101 MHz, Chloroform-d) δ 155.01, 141.45, 138.29, 133.11,130.44, 130.18, 128.53, 128.29, 128.08, 127.73, 127.20, 51.31, 48.86, 45.31,22.58.

[0197] Activity effect test

[0198] Using an in vitro method, the following compounds were analyzed: 1-phenylmethyl-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(4-methoxyphenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(4-methylphenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(4-fluorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one, and 1-(4-chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one. 1H)-one, 1-(4-tert-butylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(4-cyanobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(3-methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(3-methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one, 1-(3-chlorobenzyl)-3-phenyl Tetrahydropyrimidin-2(1H)-one, 1-(2-methylbenzyl)-3-phenyltetrahydropyrimidin-2(1H)-one, 1-(2-chlorobenzyl)-3-phenyltetrahydropyrimidin-2(1H)-one, 1-benzyl-3-(4-methoxyphenyl)tetrahydropyrimidin-2(1H)-one, 1-benzyl-3-(4-methylphenyl)tetrahydropyrimidin-2(1H)-one, 1-benzyl-3-(4-methylphenyl)tetrahydropyrimidin-2(1H)-one, 1-benzyl-3-(4-methylphenyl)tetrahydropyrimidin-2(1H)-one The bactericidal activity of 1-phenylmethyl-3-(3-tolyl)tetrahydropyrimidine-2(1H)-one, 1-phenylmethyl-3-(3-chlorophenyl)tetrahydropyrimidine-2(1H)-one, 1-phenylmethyl-3-(2-tolyl)tetrahydropyrimidine-2(1H)-one and 1-phenylmethyl-3-(2-chlorophenyl)tetrahydropyrimidine-2(1H)-one was tested.

[0199] Using wheat scab, rice blast, pepper phytoma, rapeseed sclerotium, cucumber gray mold, rice sheath blight, and apple rot as test materials for fungicidal activity testing, the test agents were dissolved in acetone and then diluted to 500 g / mL with 200 g / mL sorporl-144 emulsifier. Under aseptic conditions, 1 mL of the compound solution was pipetted into a sterilized Petri dish, followed by 9 mL of sterile PDA culture medium. The mixture was then prepared into agar plates of the appropriate concentration. Under aseptic conditions, mycelial cakes were cut from the edge of the colony using a 4 mm sterile punch. After the culture medium solidified, the mycelial cakes were inoculated into the center of the agar plate and incubated at a suitable temperature. A blank control was prepared without the added agent. Each treatment was incubated in an incubator at 24±1℃. After 72 hours, the diameter of the colonies was observed and measured. The diameter of each colony was measured vertically once using the cross-sectional method, and the average value was taken.

[0200] Growth inhibition rate (%) = (control colony diameter - treatment colony diameter) × 100 / (control colony diameter - 4 mm).

[0201] The drug concentration was 50 μg / mL. The results of the bactericidal activity test are shown in Table 2.

[0202] Table 2. Results of antibacterial activity tests on 1-arylmethyl-3-aryltetrahydropyrimidine-2(1H)-ketone compounds

[0203] compound Fusarium head blight Rice blast fungus Phytophthora Sclerotinia sclerotiorum gray mold Sheath blight fungus Rot bacteria Inhibition rate / % Inhibition rate / % Inhibition rate / % Inhibition rate / % Inhibition rate / % Inhibition rate / % Inhibition rate / % 1-Benzyl-3-phenyltetrahydropyrimidine-2(1H)-one 35.7 4.5 65.4 40.4 17.4 67.4 51.5 1-(4-Methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one 7.1 13.6 19.2 25.0 13.0 55.8 17.6 1-(4-Methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one 28.6 4.5 15.4 30.8 17.4 53.5 57.4 1-(4-Fluorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one 7.1 4.5 7.7 28.8 8.7 51.2 8.8 1-(4-Chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one 14.3 18.2 38.5 77.3 60.9 74.4 29.4 1-(4-tert-butylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one 39.3 4.5 26.9 80.0 52.2 58.1 86.8 1-(4-cyanophenylmethyl)-3-phenyltetrahydropyrimidin-2(1H)-one 3.6 18.2 7.7 21.2 8.7 55.8 83.8 1-(3-Methoxybenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one 25.0 4.5 7.7 17.3 8.7 62.8 8.8 1-(3-Methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one 32.1 4.5 53.8 59.6 13.0 48.8 47.1 1-(3-Chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one 17.9 27.3 23.1 30.8 30.4 62.8 54.4 1-(2-Methylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one 25.0 4.5 26.9 48.1 8.7 16.3 32.4 1-(2-Chlorophenylmethyl)-3-phenyltetrahydropyrimidine-2(1H)-one 25.0 4.5 19.2 50.0 13.0 32.6 70.6 1-Benzyl-3-(4-methoxyphenyl)tetrahydropyrimidine-2(1H)-one 60.7 4.5 75.4 38.5 8.7 16.3 35.3 1-Benzyl-3-(4-methylphenyl)tetrahydropyrimidine-2(1H)-one 60.7 13.6 79.2 79.2 30.4 9.3 57.4 1-Benzyl-3-(4-chlorophenyl)tetrahydropyrimidine-2(1H)-one 21.4 18.2 38.5 51.9 17.4 39.5 42.6 1-Benzyl-3-(3-Tolyl)tetrahydropyrimidine-2(1H)-one 60.7 13.6 57.7 44.2 8.7 37.2 58.8 1-Benzyl-3-(3-chlorophenyl)tetrahydropyrimidine-2(1H)-one 55.4 13.6 26.9 83.1 43.5 51.2 76.5 1-Benzyl-3-(2-Tolyl)tetrahydropyrimidine-2(1H)-one 50.0 9.1 46.2 40.4 8.7 11.6 55.9 1-Benzyl-3-(2-chlorophenyl)tetrahydropyrimidine-2(1H)-one 21.4 13.6 57.7 57.7 52.2 39.5 61.8

[0204] The table shows that the target compounds exhibit moderate to good inhibitory activity against the tested pathogens. Specifically, 1-(4-chlorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one showed an inhibition rate of 77.3% against *Sclerotinia sclerotinia* and 74.4% against *Rhizoctonia solani*; 1-(4-tert-butylbenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one showed an inhibition rate as high as 86.8% against *Pseudomonas rottensis* and 80.0% against *Sclerotinia sclerotinia*; 1-(4-cyanobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one showed an inhibition rate of 83.8% against *Pseudomonas rottensis*; and 1-(2-chlorobenzyl)-3-phenyltetrahydropyrimidine-2(1H)-one showed an inhibition rate of 83.8% against *Pseudomonas rottensis*. The inhibition rate of pyrimidine-2(1H)-one against *Pseudomonas aeruginosa* was 70.6%; the inhibition rate of 1-benzyl-3-(4-methoxyphenyl)tetrahydropyrimidine-2(1H)-one against *Phytophthora* was 75.4%; the inhibition rate of 1-benzyl-3-(4-methylphenyl)tetrahydropyrimidine-2(1H)-one against both *Sclerotinia sclerotiorum* and *Phytophthora* was 79.2%; the inhibition rate of 1-benzyl-3-(3-chlorophenyl)tetrahydropyrimidine-2(1H)-one against *Sclerotinia sclerotiorum* was as high as 83.1%, and the inhibition rate against *Pseudomonas aeruginosa* was 76.5%.

[0205] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Although the present invention has been disclosed above with reference to preferred embodiments, it is not intended to limit the present invention. Any person skilled in the art can make some modifications or alterations to the above-described technical content to create equivalent embodiments without departing from the scope of the present invention. Any simple modifications, equivalent changes, and alterations made to the above embodiments based on the technical essence of the present invention without departing from the scope of the present invention shall still fall within the scope of the present invention.

Claims

1. A 1-arylmethyl-3-aryl tetrahydropyrimidin-2(lH)-one compound, characterized in that, The compound has a structural general formula (VI), ； (VI) In formula (VI), R1 is hydrogen, C1-C3 alkyl, C1-C2 alkoxy, halogen, cyano or tert-butyl; R2 is hydrogen, C1-C3 alkyl or C1-C2 alkoxy.

2. The 1-arylmethyl-3-aryl tetrahydropyrimidin-2(lH)-one compound according to claim 1, characterized by, R1 is H, 4-CH3O, 4-CH3, 4-Cl, 4-F, 4-C(CH3)3, 4-CN, 3-CH3, 3-CH3O, 3-Cl, 2-CH3 or 2-Cl; R2 is 4-CH3O, 4-CH3, 4-Cl, 3-CH3, 3-Cl, 2-CH3 or 2-Cl.

3. The 1-arylmethyl-3-aryl tetrahydropyrimidin-2(lH)-one compound according to claim 1, characterized by, The compound is selected from one or more of the following compounds: 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: 。 4. A process for the preparation of 1-arylmethyl-3-aryl tetrahydropyrimidin-2(lH)-ones of general structure (VI) characterized in that, 1-phenyl-3-(2-chlorophenyl)tetrahydropyrimidin-2(1H)-one: ； The structural general formula (VI) is: The preparation method specifically comprises the following steps: S1, the aryl iodide with structural formula (I) and the 1,3-propanediamine with structural formula (II) are subjected to Ullmann coupling reaction under the action of CuCl to obtain an N-aryl-1,3-propanediamine compound with structural formula (III), and then N-alkylation is performed with arylmethyl chloride with structural formula (IV) to obtain an N-arylmethyl-N'-arylpropanediamine compound with structural formula (V): ； S2, the N-arylmethyl-N'-arylpropanediamine compound having the general structure (V) is dissolved in an organic solvent, alkali is added, CO2 gas is introduced, p-toluenesulfonyl chloride is added, and a 1-arylmethyl-3-aryl tetrahydropyrimidine-2(1H)-one compound having the general structure (VI) is prepared: ； In the formula, R1 is hydrogen, C1-C3 alkyl, C1-C2 alkoxy, halogen, cyano or tert-butyl; R2 is hydrogen, C1-C3 alkyl or C1-C2 alkoxy.

5. The preparation method according to claim 4, characterized in that, R1 is H, 4-CH3O, 4-CH3, 4-Cl, 4-F, 4-C(CH3)3, 4-CN, 3-CH3, 3-CH3O, 3-Cl, 2-CH3 or 2-Cl; R2 is 4-CH3O, 4-CH3, 4-Cl, 3-CH3, 3-Cl, 2-CH3 or 2-Cl.

6. The preparation method of claim 4, wherein, Step S1 is specifically: the Ullmann coupling reaction of aryl iodide with the structure of (I) and 1,3-propanediamine with the structure of (II) is carried out with KOH as the base and CuCl as the catalyst to obtain an N-aryl-1,3-propanediamine compound with the structure of (III), and finally the N-alkylation of the N-aryl-1,3-propanediamine compound with the structure of (III) and arylmethyl chloride with the structure of (IV) is carried out in acetonitrile solvent with K2CO3 as the base to obtain an N-arylmethyl-N'-arylpropanediamine compound with the structure of (V); Step S2 is specifically: the N-arylmethyl-N'-arylpropanediamine compound with the structure of (V) is added to an organic solvent, a base is added, CO2 gas is introduced, the system is stirred for a certain time, and finally p-toluenesulfonyl chloride is added to the mixed system for reaction, separation, and obtaining a 1-arylmethyl-3-aryl tetrahydropyrimidine-2(1H)-one compound having the general structure (VI).

7. The preparation method of claim 4, wherein, In step S1, the molar ratio of aryl iodide with the general structure (I), 1,3-propanediamine with the structure of (II), KOH and CuCl added to the reaction is 1:2-3:1-2:0.1-0.3; the molar ratio of N-aryl-1,3-propanediamine compound with the structure of (III), arylmethyl chloride with the structure of (IV) and K2CO3 added to the reaction is 1:1-1.2:1.5-2; In step S2, the molar ratio of N-arylmethyl-N'-arylpropanediamine compound with the general structure of (V), base and p-toluenesulfonyl chloride is 1:1.5-2.0:1.0-1.

5.

8. The preparation method of claim 4, wherein, In step S2, the organic solvent is dichloromethane, N,N-dimethylformamide, toluene, dimethyl sulfoxide or acetonitrile; the base is triethylamine, triethylene diamine, 1,8-diazabicyclo[5.4.0]undec-7-ene or 4-dimethylamino pyridine.

9. Use of 1-arylmethyl-3-aryl-tetrahydropyrimidin-2(lH)-ones of the general structure (VI) according to any one of claims 1 to 3 or of 1-arylmethyl-3-aryl-tetrahydropyrimidin-2(lH)-ones of the general structure (VI) prepared according to a process according to any one of claims 4 to 8, characterized in that, A medicine for inhibiting bacteria of crops is prepared.

10. Use according to claim 9, characterized in that, A medicament for inhibiting one or more of pythium, sheath blight, damping-off, and scab.

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