A uracil benzene ring ester compound, a preparation method thereof and a pesticide composition

Abstract

The application provides a uracil phenyl ring ester compound as shown in formula (I), wherein R1 and R2 are independently selected from hydrogen, amino, C1-C4 alkyl or C1-C4 haloalkyl; X and Y are independently selected from hydrogen, halogen or cyano; Z is selected from an oxygen atom or a sulfur atom; and R3 is C1-C8 alkoxycarbonyl, C1-C8 alkoxycarbonyl-substituted C1-C8 alkyl, C1-C8 alkoxycarbonyl-substituted C1-C8 alkoxy, C1-C8 alkoxycarbonyl-substituted C2-C8 alkenyl or C1-C8 alkoxycarbonyl-substituted C2-C8 alkynyl. The uracil phenyl ring ester compound has high selectivity, a wide herbicidal spectrum and good effect on preventing and treating broadleaf weeds such as amaranth and gramineous weeds such as barnyard grass. The application further provides a preparation method and a pesticide composition of the uracil phenyl ring ester compound.

Description

Technical Field

[0001] This invention relates to the field of organic compound technology, specifically to a uracil phenylcyclic ester compound, its preparation method, and a pesticide composition thereof. Background Technology

[0002] Currently, the main method for weed control is spraying herbicides. However, with the widespread use of herbicides (such as glyphosate), many weeds have developed resistance, especially barnyard grass, goosegrass, and sedge, which have become dominant and noxious weeds. Many herbicides on the market generally suffer from poor control efficacy, narrow weed removal range, and require high dosages, showing poor effectiveness against noxious weeds like barnyard grass and goosegrass. Furthermore, as selective herbicides, they often adversely affect crop growth, causing significant economic losses, particularly to vegetable crops such as bok choy.

[0003] Therefore, it is necessary to provide a new type of herbicide compound that is highly selective, has a broad spectrum of weed control, is less likely to induce resistance in weeds, and is particularly effective against noxious weeds such as barnyard grass, while being safe for weeds such as Chinese cabbage. Summary of the Invention

[0004] In view of this, this application provides a uracil phenyl ester compound, which has the advantages of high selectivity, broad spectrum of weed control, and low resistance of weeds. It has a good control effect on noxious weeds such as barnyard grass, Echinochloa crus-galli, and amaranth, and has low toxicity to mammals and minimal impact on crops.

[0005] The first aspect of this application provides a uracil phenyl ester compound as shown in formula (Ⅰ):

[0006]

[0007] In formula (Ⅰ), R1 and R2 are independently selected from hydrogen, amino, C1-C4 alkyl or C1-C4 haloalkyl, respectively;

[0008] X and Y are independently selected from hydrogen, halogen, or cyano groups, respectively;

[0009] Z is selected from oxygen or sulfur atoms;

[0010] R3 is a C1-C8 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C8 alkoxycarbonyl, a C1-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C8 alkoxycarbonyl, or a C2-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl.

[0011] In the embodiments of this application, R3 is a C1-C4 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C4 alkoxycarbonyl, a C1-C8 alkoxy group substituted with a C1-C4 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C4 alkoxycarbonyl, or a C2-C8 alkynyl group substituted with a C1-C4 alkoxycarbonyl.

[0012] In the embodiments of this application, R3 is a C1-C4 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C4 alkoxycarbonyl, a C1-C8 alkoxy group substituted with a C1-C4 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C4 alkoxycarbonyl, or a C2-C8 alkynyl group substituted with a C1-C4 alkoxycarbonyl.

[0013] In the embodiments of this application, R3 is a C1-C2 alkoxycarbonyl, a C1-C4 alkyl group substituted with a C1-C2 alkoxycarbonyl, a C1-C2 alkoxycarbonyl group substituted with a C1-C2 alkoxycarbonyl, a C2-C4 alkenyl group substituted with a C1-C2 alkoxycarbonyl, or a C2-C4 alkynyl group substituted with a C1-C2 alkoxycarbonyl.

[0014] In the embodiments of this application, R1 is a C1-C4 perfluoroalkyl group; R2 is a C1-C4 alkyl group; and X and Y are halogens.

[0015] In this embodiment of the application, R1 is trifluoromethyl; R2 is methyl or ethyl; and X and Y are independently selected from fluorine or chlorine.

[0016] A second aspect of this application also provides a method for preparing uracil phenylcyclic ester compounds, comprising the following steps:

[0017] Provide compound A as shown in formula (II) and compound B as shown in formula (III).

[0018]

[0019] R1 and R2 are independently selected from hydrogen, amino, C1-C4 alkyl or C1-C4 haloalkyl;

[0020] X and Y are independently selected from hydrogen, halogen, or cyano groups, respectively;

[0021] Z is selected from oxygen or sulfur atoms;

[0022] R3 is a C1-C8 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C8 alkoxycarbonyl, a C1-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C8 alkoxycarbonyl, or a C2-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl.

[0023] Compound A and compound B were mixed, a catalyst was added to carry out the reaction, and after the reaction was completed, the solid product was collected and purified to obtain uracil phenyl cyclic ester compounds as shown in formula (I).

[0024]

[0025] In this embodiment of the application, the reaction temperature is 0℃-160℃.

[0026] In this embodiment of the application, the reaction time is 2h-15h.

[0027] A third aspect provides a pesticide composition comprising an active component, the active component comprising a uracil phenyl ester compound or a pesticide-acceptable salt thereof provided in the first aspect of this application, or a uracil phenyl ester compound or a pesticide-acceptable salt thereof prepared by the method for preparing uracil phenyl ester compounds provided in the second aspect of this application; the active component in the pesticide composition has a mass percentage content of 1%-99%.

[0028] The fourth aspect of this application also provides the use of the uracil phenylcyclic ester compound provided in the first aspect of this application or the pesticide composition provided in the third aspect in a herbicide or defoliant. Detailed Implementation

[0029] The technical solutions in the embodiments of this application are described clearly and completely below. Obviously, the described embodiments are only a part of the embodiments of this application, and not all of the embodiments. Based on the embodiments in this application, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of this application.

[0030] Because weeds compete with crops for sunlight and fertilizer, they cause significant losses to agricultural production every year. Currently, the main method for weed control is spraying herbicides. However, with the widespread use of herbicides (such as glyphosate), many weeds have developed resistance, especially barnyard grass, goosegrass, and elm, which have become dominant and noxious weeds. Many herbicides currently on the market generally suffer from poor control efficacy, narrow weed removal range, and require high dosages, showing poor effectiveness against noxious weeds like barnyard grass and goosegrass. Furthermore, as selective herbicides, they often have adverse effects on crop growth, causing substantial economic losses, particularly to vegetable crops such as bok choy.

[0031] Therefore, it is necessary to provide a new type of herbicide compound that is highly selective, has a broad spectrum of weed control, is less likely to induce resistance in weeds, and is particularly effective against noxious weeds such as barnyard grass, while being safe for weeds such as Chinese cabbage.

[0032] In view of this, this application provides a uracil phenyl ester compound, which has the advantages of high selectivity, broad spectrum of weed control, and low resistance of weeds. It has a good control effect on noxious weeds such as barnyard grass, Echinochloa crus-galli, and amaranth, and has low toxicity to mammals and minimal impact on crops.

[0033] This application provides a uracil phenyl ester compound as shown in formula (Ⅰ):

[0034]

[0035] In formula (Ⅰ), R1 and R2 are independently selected from hydrogen, amino, C1-C4 alkyl or C1-C4 haloalkyl, respectively;

[0036] X and Y are independently selected from hydrogen, halogen, or cyano groups, respectively;

[0037] Z is selected from oxygen or sulfur atoms;

[0038] R3 is a C1-C8 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C8 alkoxycarbonyl, a C1-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C8 alkoxycarbonyl, or a C2-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl.

[0039] In this application, R1 and R2 are independently selected from C1-C4 alkyl or C1-C4 haloalkyl groups. In some embodiments of this application, the C1-C4 alkyl group may be, for example, methyl, ethyl, propyl, isopropyl, or butyl; the C1-C4 haloalkyl group may be, for example, methyl, ethyl, propyl, isopropyl, or butyl groups substituted with at least one halogen atom. In this application, the halogen atom in the C1-C4 haloalkyl group may be a fluorine atom, a chlorine atom, or a bromine atom. In this application, the C1-C4 haloalkyl group may have one or more halogen atoms.

[0040] In some embodiments of this application, R1 and R2 are independently C1-C2 alkyl or C1-C2 haloalkyl groups. In some specific embodiments of this application, R1 and R2 can be, for example, methyl, ethyl, monochloromethyl, dichloromethyl, trichloromethyl, monofluoromethyl, difluoromethyl, or trifluoromethyl groups. R1 and R2 can be the same group or different groups. In some specific embodiments of this application, R1 can be, for example, trifluoromethyl; and R2 can be, for example, methyl.

[0041] In the embodiments of this application, R3 can be at any position on the benzene ring, and R3 can be in the ortho, meta, or para position of Z.

[0042] In this application, C1-C8 alkoxycarbonyl groups include straight-chain alkoxycarbonyl groups with 1-8 carbon atoms, branched-chain alkoxycarbonyl groups with 1-8 carbon atoms, and cycloalkoxycarbonyl groups with 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C1-C8 alkoxycarbonyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, or 8. In some embodiments of this application, the C1-C8 alkoxycarbonyl group can be, for example, -COOCH3, -COOCH2CH3, -COOCH2CH2CH3, -COOCH(CH3)2, -COOCH(CH3)CH2CH3, -COOC(CH3)3, -COOCH(CH2CH2), or -COOC(CH2CH2)CH3.

[0043] In this application, C1-C8 alkyl groups include straight-chain alkyl groups with 1-8 carbon atoms, branched-chain alkyl groups with 1-8 carbon atoms, and cycloalkyl groups with 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C1-C8 alkyl groups may be, for example, 1, 2, 3, 4, 5, 6, 7, or 8. In this application, C1-C8 alkoxy groups include straight-chain alkoxy groups with 1-8 carbon atoms, branched-chain alkoxy groups with 1-8 carbon atoms, and cycloalkoxy groups with 3-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C1-C8 alkoxy groups may be, for example, 1, 2, 3, 4, 5, 6, 7, or 8.

[0044] In this application, the C2-C8 alkenyl group includes a straight-chain alkenyl group with 2-8 carbon atoms and a branched alkenyl group with 2-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C2-C8 alkenyl group can be, for example, 2, 3, 4, 5, 6, 7, or 8. In this application, the C2-C8 yntyl group includes a straight-chain yntyl group with 2-8 carbon atoms and a branched yntyl group with 2-8 carbon atoms. In some embodiments of this application, the number of carbon atoms in the C2-C8 yntyl group can be, for example, 2, 3, 4, 5, 6, 7, or 8.

[0045] In some embodiments of this application, R3 is a C1-C4 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C4 alkoxycarbonyl, a C1-C8 alkoxy group substituted with a C1-C4 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C4 alkoxycarbonyl, or a C2-C8 alkynyl group substituted with a C1-C4 alkoxycarbonyl.

[0046] In some specific embodiments of this application, R3 is a C1-C2 alkoxycarbonyl, a C1-C4 alkyl group substituted with a C1-C2 alkoxycarbonyl, a C1-C2 alkoxycarbonyl group substituted with a C1-C2 alkoxycarbonyl, a C2-C4 alkenyl group substituted with a C1-C2 alkoxycarbonyl, or a C2-C4 alkynyl group substituted with a C1-C2 alkoxycarbonyl.

[0047] In some embodiments of this application, R1 is a C1-C4 perfluoroalkyl group; R2 is a C1-C4 alkyl group; and X and Y are halogens.

[0048] In some embodiments of this application, R1 is trifluoromethyl; R2 is methyl or ethyl; and X and Y are each independently selected from fluorine or chlorine.

[0049] Compared to traditional herbicides, the uracil phenylcyclic ester compounds provided in this application exhibit stronger herbicidal effects and greater selectivity. By selecting appropriate functional groups, the selectivity of these compounds can be enhanced, and the range of weeds they control can be broadened. They effectively remove noxious weeds while minimizing impact on existing plants or crops. The selection of individual functional groups in the structure of these phenylcyclic ester compounds maximizes their selectivity and herbicidal spectrum, resulting in high selectivity, a broad herbicidal spectrum, and reduced resistance in weeds. They are particularly effective against noxious weeds such as barnyard grass, and exhibit low toxicity to mammals and minimal impact on crops.

[0050] This application also provides a method for preparing uracil phenyl cyclic ester compounds, comprising the following steps:

[0051] S101. Provide compound A as shown in formula (II) and compound B as shown in formula (III).

[0052]

[0053] R1 and R2 are independently selected from hydrogen, amino, C1-C4 alkyl or C1-C4 haloalkyl;

[0054] X and Y are independently selected from hydrogen, halogen, or cyano groups, respectively;

[0055] Z is selected from oxygen or sulfur atoms;

[0056] R3 is a C1-C8 alkoxycarbonyl, a C1-C8 alkyl group substituted with a C1-C8 alkoxycarbonyl, a C1-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl, a C2-C8 alkenyl group substituted with a C1-C8 alkoxycarbonyl, or a C2-C8 alkoxycarbonyl group substituted with a C1-C8 alkoxycarbonyl.

[0057] S102. Compound A and compound B are mixed, a catalyst is added to carry out the reaction, and after the reaction is complete, the solid product is collected and purified to obtain a uracil phenyl cyclic ester compound as shown in formula (I).

[0058]

[0059] In this embodiment of the application, the catalyst in step S102 includes, but is not limited to, a bound acid catalyst.

[0060] In this embodiment of the application, the reaction temperature in step S102 is 0℃-160℃. In some embodiments of the application, the reaction temperature in step S102 may be, for example, 0℃, 10℃, 20℃, 30℃, 50℃, 80℃, 100℃, 120℃, 150℃, or 160℃.

[0061] In this embodiment of the application, the reaction time in step S102 is 2h-15h. In some embodiments of the application, the reaction time in step S102 may be, for example, 2h, 3h, 5h, 8h, 10h, 12h, or 15h.

[0062] The preparation method of uracil phenylcyclic ester compounds provided in this application is simple and convenient, with low pollution and high yield, and the preparation method can be applied to industrial production. The uracil phenylcyclic ester compounds prepared by the method of this invention have advantages such as high selectivity, low dosage, broad herbicidal spectrum, and low susceptibility to weed resistance, especially showing good control effect against noxious weeds such as barnyard grass. Furthermore, they have low toxicity to mammals and minimal impact on crops.

[0063] This application also provides a pesticide composition comprising an active ingredient, said active ingredient comprising uracil phenylcyclic ester compounds or their pesticide-acceptable salts as provided above in this application, or uracil phenylcyclic ester compounds or their pesticide-acceptable salts prepared by the method for preparing uracil phenylcyclic ester compounds as provided above in this application; the active ingredient in the pesticide composition has a mass percentage content of 1%-99%. In some embodiments of this application, the mass percentage content of the active ingredient in the pesticide composition may be, for example, 1%, 2%, 5%, 8%, 5%, 10%, 20%, 25%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, or 99%. In embodiments of this application, the pesticide composition may be used by means including but not limited to spraying.

[0064] This application also provides the application of the uracil phenyl ester compounds or pesticide compositions provided above in herbicides or defoliants. In some embodiments of this application, the uracil phenyl ester compound is used in a herbicide, and the mass percentage of the uracil phenyl ester compound in the herbicide is 0.1%-99.9%. In some specific embodiments of this application, the mass percentage of the uracil phenyl ester compound in the herbicide can be, for example, 0.1%, 0.5%, 1%, 2%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 50%, 60%, 70%, 80%, 90%, or 99.9%. In some specific examples of this application, the mass percentage of the uracil phenyl ester compound in the herbicide can be 0.1%-40%. Applying the uracil phenylcyclic ester compounds provided in this application to herbicides can yield herbicides that are highly selective, require low dosage, have a broad spectrum of weed control, and are less likely to induce resistance in weeds, especially showing good control effects against noxious weeds such as barnyard grass.

[0065] In other embodiments of this application, the uracil phenylcyclic ester compound is used in a defoliant, and the mass percentage of the uracil phenylcyclic ester compound in the defoliant is 0.1%-99.9%. In some specific embodiments of this application, the mass percentage of the uracil phenylcyclic ester compound in the herbicide can be, for example, 0.1%, 1%, 5%, 10%, 15%, 20%, 23%, 25%, 28%, 30%, 32%, 35%, 38%, 40%, 43%, 45%, 48%, 50%, 60%, 70%, 80%, 90%, or 99.9%. In some specific examples of this application, the mass percentage of the uracil phenylcyclic ester compound in the herbicide can be 20%-50%. The uracil phenyl cyclic ester compounds provided in this application can be used as defoliants to meet the defoliation needs of various plants. For example, the defoliants have been used to induce defoliation in cotton crops and have shown significant defoliation effects.

[0066] The embodiments of this application will be further described below through multiple examples.

[0067] Specifically, the uracil phenyl ester compounds described in this application are listed in Table 1, but the phenyl ester compounds described in this invention are not limited to all the compounds in Table 1.

[0068]

[0069] Note: The position adjacent to R3 on the benzene ring is denoted as position 1, the position meta of R3 on the benzene ring is denoted as position 2, and the position para of R3 on the benzene ring is denoted as position 3.

[0070] Table 1: Uracil phenyl cyclic ester compounds with chemical structures as shown in formula (Ⅰ):

[0071]

[0072]

[0073]

[0074] Example 1

[0075] The preparation methods of uracil phenylcyclic ester compounds shown in Table 1 (compound number 1) are as follows:

[0076]

[0077] (1) 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid (1.0 g, 0.0026 mol) was added to thionyl chloride and heated under reflux at room temperature for 6 h. The solution was then evaporated to dryness to obtain the target product 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride (0.8387 g, 0.0022 mol), with a yield of 84%. The 1H NMR spectrum of the 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride was characterized as follows: 1H-NMR (600MHz, DMSO), with the following data: δ: 8.544 (d, J = 7.6Hz, 1H, Ar), 8.072 (d, J = 9.6Hz, 1H, Ar), 6.876 (s, 1H, CH), 3.984 (s, 3H, -CH3). Solution A was prepared by dissolving 1.0 g (0.0026 mol) of 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride in 20 mL of dichloromethane. The 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid is shown as formula (IV), and the 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride is shown as formula (V).

[0078]

[0079] (2) Dissolve methyl 3-hydroxybenzoate (0.4200 g, 0.0027 mol) in 5 mL of dichloromethane, add it to the prepared acyl chloride, and after reacting for two minutes, add 0.4 mL (0.2912, 0.0029 mol) of triethylamine and react at room temperature for 5 h. After the reaction is complete, wash twice with dilute hydrochloric acid, and then separate by column chromatography. Drying yields methyl 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoate-3-hydroxybenzoate, a white solid as shown in formula (2), with a yield of 88%.

[0080] 1H NMR characterization: 1H-NMR (500MHz, CDCl3), data are as follows: δ: 8.16(d,1H,Ph-H), 8.06(d,1H,Ph-H), 7.90(s,2H,Ph-H), 7.54(d,1H,Ph-H), 7.50(t,1H,Ph-H), 7.46(d,1H,Ph-H), 6.42(s,1H,CH), 3.95(s,3H,CH3), 3.61(s,3H,CH3), ESI[M+Na]+ m / z 523.02924.

[0081] Example 2

[0082] The preparation methods of uracil phenylcyclic ester compounds shown in Table 1 (compound number 17) are as follows:

[0083]

[0084] (1) 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid (1.0 g, 0.0026 mol) was added to thionyl chloride and heated under reflux at room temperature for 6 h. The solution was then evaporated to dryness to obtain the target product 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride (0.8387 g, 0.0022 mol), with a yield of 84%. The 1H NMR spectrum of the 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride was characterized as follows: 1H-NMR (400MHz, DMSO), with the following data: δ: 8.544 (d, J = 7.6Hz, 1H, Ar), 8.072 (d, J = 9.6Hz, 1H, Ar), 6.876 (s, 1H, CH), 3.984 (s, 3H, -CH3).

[0085] (2) Dissolve methyl 2-hydroxyphenylacetate (0.4540 g, 0.0027 mol) in 5 mL of dichloromethane, add it to solution A, and after reacting for two minutes, add 0.4 mL (0.2912, 0.0029 mol) of triethylamine. React at room temperature for 6 h. After the reaction is complete, wash twice with dilute hydrochloric acid, then wash with a mixture of saturated sodium bicarbonate and saturated sodium chloride solution. Finally, separate by column chromatography and dry to obtain methyl 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoic acid-2-hydroxyphenylacetate as shown in formula (1), with a yield of 89%.

[0086] Example 3

[0087] Preparation methods of uracil phenylcyclic ester compounds, as shown in compound number 40 in Table 1:

[0088]

[0089] (1) 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoic acid (1.0 g, 0.0026 mol) was added to thionyl chloride and heated under reflux at room temperature for 6 h. The solution was then evaporated to dryness to obtain the target product 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride (0.8387 g, 0.0022 mol), with a yield of 84%. The 1H NMR spectrum of the 2-chloro-4-fluoro-5-(1,2,3,6-tetrahydro-2,6-dioxo-4-trifluoromethylpyrimidin-1-yl)benzoyl chloride was characterized as follows: 1H-NMR (400MHz, DMSO), with the following data: δ: 8.544 (d, J = 7.6Hz, 1H, Ar), 8.072 (d, J = 9.6Hz, 1H, Ar), 6.876 (s, 1H, CH), 3.984 (s, 3H, -CH3).

[0090] (2) Dissolve ethyl 2-(2-hydroxyphenoxy)acetic acid ester (0.5460 g, 0.0027 mol) in 5 mL of dichloromethane, add it to the prepared acyl chloride, and after reacting for two minutes, add 0.4 mL (0.2912, 0.0029 mol) of triethylamine and react at room temperature for 4 h. After the reaction is complete, wash twice with dilute hydrochloric acid, then wash with a mixture of saturated sodium bicarbonate and saturated sodium chloride solution, and finally separate by column chromatography. After drying, the light white solid 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-2,3-dihydropyrimidin-1(6H)-yl)benzoate ethyl-2-(2-hydroxyphenoxy)acetic acid ester as shown in formula (3) has a yield of 89%.

[0091] 1H NMR characterization: 1H-NMR (500MHz, CDCl3), data as follows: δ: 8.37(d, 1H, Ph-H), 7.44(d, 1H, Ph-H), 7.24(m, 2H, Ph-H), 7.07(t, 1H, Ph-H), 6.93(t, 1H, Ph-H), 6.40(s, 1H, CH), 4.63(s, 2H, CH2), 4.20(m, 3H, CH3), 3.60(s, 3H, CH3), 1.25(t, 3H, CH3), ESI [M+Na]+ m / z 567.05545.

[0092] In this embodiment of the invention, the uracil phenylcyclic ester compounds listed in Table 1 can be prepared by adjusting the preparation method described in the above embodiments; this will not be discussed in detail here. Equivalent variations made in the claims are still within the scope of the invention.

[0093] Effect Example

[0094] The herbicidal activity of some compounds listed in Table 1 of this application against various pests was determined using a post-emergence foliar treatment method. The experimental steps included:

[0095] (1) Fill flowerpots with soil that has not been treated with pesticides, then sow the seeds and allow them to germinate and grow. When the dicotyledons have grown to the two-leaf-one-heart stage and the monocotyledons have grown to the 2-3-leaf stage, perform foliar spraying (when applying this compound, the compound is first dissolved in a small amount of organic solvent, then a small amount of emulsifier is added, and then diluted with water to obtain a solution containing the compound). The control group is the commercial compound bensulfuron-methyl (control compound), wherein bensulfuron-methyl is shown in formula (VI).

[0096]

[0097] (2) The plants were naturally grown under laboratory conditions and the potted plants were watered every day. The results of the investigation after 15 days of herbicide treatment are shown in Table 3. The herbicide scoring criteria are shown in Table 2. In this experiment, the target plants were common grass weeds: barnyard grass and Echinochloa crus-galli, as well as broadleaf weeds: amaranth and purslane.

[0098] Table 2: Herbicide Scoring Criteria

[0099]

[0100] Table 3: Comparison of herbicidal activity and crop safety scores of some aryluracil phenylcyclic ester compounds in Table 1 with control compounds.

[0101]

[0102]

[0103] Note: Compound numbers correspond to those in Table 1.

[0104] The results show that the aryluracil phenylcyclic ester compounds provided by this invention have high herbicidal activity against both grasses and broadleaf weeds; while the existing pyrimethanil has herbicidal activity against broadleaf weeds but poor effect on grasses. Therefore, the aryluracil phenylcyclic ester compounds provided by this invention have a wide weed control range and high herbicidal activity. At the same time, the aryluracil phenylcyclic ester compounds have good safety for Chinese cabbage.

[0105] The preferred embodiments have been described in detail above, but the present invention is not limited to the specific implementation methods described above. Those skilled in the art can make various specific modifications under the guidance of this application without departing from the scope of protection of this application, and these modifications all fall within the scope of protection of the present invention.

Claims

1. A uracil phenylcyclic ester compound as shown in formula (Ⅰ): （Ⅰ）； In formula (Ⅰ), R1 is a C1-C4 perfluoroalkyl group; R2 is a C1-C4 alkyl group; X and Y are halogens; Z is selected from oxygen or sulfur atoms; R3 is a C1-C4 alkoxycarbonyl, a C1-C4 alkyl group substituted with a C1-C4 alkoxycarbonyl, or a C1-C4 alkoxy group substituted with a C1-C4 alkoxycarbonyl.

2. The uracil phenylcyclic ester compound according to claim 1, characterized in that, R1 is trifluoromethyl; R2 is methyl or ethyl; X and Y are each independently selected from fluorine or chlorine.

3. A method for preparing a uracil phenylcyclic ester compound, characterized in that, Includes the following steps: Provide compound A as shown in formula (II) and compound B as shown in formula (III). （Ⅱ）； （Ⅲ）； Wherein, R1 is a C1-C4 perfluoroalkyl group; R2 is a C1-C4 alkyl group; X and Y are halogens; Z is selected from oxygen or sulfur atoms; R3 is a C1-C4 alkoxycarbonyl, a C1-C4 alkyl group substituted with a C1-C4 alkoxycarbonyl, or a C1-C4 alkoxycarbonyl group substituted with a C1-C4 alkoxycarbonyl. Compound A and compound B were mixed, a catalyst was added to carry out the reaction, and after the reaction was completed, the solid product was collected and purified to obtain a uracil phenyl cyclic ester compound as shown in formula (I). （Ⅰ）。 4. The method for preparing uracil phenylcyclic ester compounds as described in claim 3, characterized in that, The reaction temperature is 0℃-160℃.

5. The method for preparing uracil phenylcyclic ester compounds as described in claim 3 or 4, characterized in that, The reaction time is 2 h to 15 h.

6. A pesticide composition, characterized in that, The pesticide composition includes an active component, which includes a uracil phenyl ester compound as described in any one of claims 1-2 or a pesticide-acceptable salt thereof, or a uracil phenyl ester compound or a pesticide-acceptable salt thereof prepared by the method described in any one of claims 3-5; the active component in the pesticide composition has a mass percentage of 1%-99%.

7. The use of a uracil phenyl cyclic ester compound as described in any one of claims 1-2 or a pesticide composition as described in claim 6 in a herbicide or defoliant.

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