Uracil compound and use thereof

Abstract

Disclosed in the present invention are a uracil compound and a use thereof. The structure of the compound is as represented by general formula I. Also disclosed is a use of the uracil compound as a herbicide.

Description

A uracil compound and its application Technical Field

[0001] This invention belongs to the field of agricultural herbicides. Specifically, it relates to a uracil compound and its applications. Background Technology

[0002] Patent CN1316426A discloses the following herbicide compound CK1 (compound number: 7-8, CAS Registry Number: 353292-31-6). This compound has been commercially used as an agricultural herbicide, with its common Chinese name being flupyrimidine and its common English name being Epyrifenacil. This compound is a phenyluracil herbicide developed by Sumitomo Chemical Co., Ltd. of Japan.

[0003] In the prior art, there are no reports on uracil compounds such as those shown in this invention and their herbicidal activity. Summary of the Invention

[0004] In order to develop new herbicides to solve the increasingly serious problem of herbicide resistance, this invention provides a novel uracil compound and its application.

[0005] To achieve the above objectives, the technical solution adopted by the present invention is as follows:

[0006] A uracil compound, as shown in general formula I:

[0007] In general formula I:

[0008] R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, amino, C1-C6 alkyl or halo-C1-C6 alkyl;

[0009] X is selected from O or S;

[0010] Q is selected from one of the groups shown in Q1-Q3:

[0011] Q1: -CH2OR3;

[0012] Q2: -CH2S (=O) m R4;

[0013] Q3:

[0014] R3 and R4 are each independently selected from C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl carbonyloxy C1-C6 alkyl, C1-C6 alkoxy carbonyl C1-C6 alkyl carbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6, phenyl, benzyl or phenyl carbonyl, and when the number of substituents is greater than 1, R6 may be the same or different;

[0015] m is selected from 0, 1, or 2;

[0016] n is selected from 1, 2, 3, 4, or 5;

[0017] R5 and R6 are each independently selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkylthio or halo-C1-C6 alkylthio.

[0018] It may be a stereoisomer of a compound of general formula I;

[0019] Or it may be a salt of a compound of general formula I;

[0020] It may be a salt of a stereoisomer of a compound of general formula I.

[0021] In one possible implementation, in general formula I,

[0022] R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, amino, C1-C4 alkyl or halo-C1-C4 alkyl;

[0023] X is selected from O or S;

[0024] Q is selected from one of the groups shown in Q1-Q3:

[0025] Q1: -CH2OR3;

[0026] Q2: -CH2S (=O) m R4;

[0027] Q3:

[0028] R3 and R4 are each independently selected from C1-C4 alkyl, halo-C1-C4 alkyl, C1-C4 alkyl carbonyl, C1-C4 alkoxy carbonyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkyl carbonyloxy C1-C4 alkyl, C1-C4 alkoxy carbonyl C1-C4 alkyl carbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6, phenyl, benzyl or phenyl carbonyl, and when the number of substituents is greater than 1, R6 may be the same or different;

[0029] m is selected from 0, 1, or 2;

[0030] n is selected from 1, 2, 3, 4, or 5;

[0031] R5 and R6 are each independently selected from halogen, cyano, nitro, C1-C4 alkyl, halo-C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C1-C4 alkylthio or halo-C1-C4 alkylthio.

[0032] It may be a stereoisomer of a compound of general formula I;

[0033] Salts formed by compounds of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

[0034] Salts formed by the stereoisomer of a compound of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

[0035] In one possible implementation, in general formula I,

[0036] R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, amino, C1-C4 alkyl or halo-C1-C4 alkyl;

[0037] X is selected from O or S;

[0038] Q is selected from one of the groups shown in Q1-Q3:

[0039] Q1: -CH2OR3;

[0040] Q2: -CH2S (=O) m R4;

[0041] Q3:

[0042] R3 and R4 are each independently selected from C1-C4 alkyl, halo-C1-C4 alkyl, C1-C4 alkyl carbonyl, C1-C4 alkoxy carbonyl, C1-C4 alkoxy C1-C2 alkyl, C1-C4 alkyl carbonyloxy C1-C2 alkyl, C1-C4 alkoxy carbonyl C1-C2 alkyl carbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6, phenyl, benzyl or phenyl carbonyl, and when the number of substituents is greater than 1, R6 may be the same or different;

[0043] m is selected from 0, 1, or 2;

[0044] n is selected from 1, 2, 3, 4, or 5;

[0045] R5 and R6 are each independently selected from halogen, cyano, nitro, C1-C4 alkyl, halo-C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C1-C4 alkylthio or halo-C1-C4 alkylthio.

[0046] It may be a stereoisomer of a compound of general formula I;

[0047] Salts formed by compounds of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

[0048] Salts formed by the stereoisomer of a compound of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

[0049] In one possible implementation, in general formula I,

[0050] R1 and R2 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, or perfluoroethyl.

[0051] X is selected from O or S;

[0052] Q is selected from one of the groups shown in Q1-Q3:

[0053] Q1: -CH2OR3;

[0054] Q2: -CH2S (=O) m R4;

[0055] Q3:

[0056] R3 and R4 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, perfluoroethyl, 1,1,1,3,3,3-hexafluoropropane-2-yl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, CH3OCH2-, CH3CH2OC H2-, CH3CH2CH2OCH2-, (CH3)2CHOCH2-, CH3CH2CH2CH2OCH2-, (CH3)3COCH2-, CH3OCH2CH2-, CH3CH2OCH2CH2-, CH3CH2CH2OCH2CH2-, CH3CH2CH2CH2OCH2CH2-, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, methylcarbonyloxyethyl, ethylcarbonyloxyethyl, methoxycarbonylmethylcarbonyl, ethoxycarbonylmethylcarbonyl, tert-butoxycarbonylethylcarbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6 groups, and when the number of substituents is greater than 1, the R6 groups may be the same or different;

[0057] m is selected from 0, 1, or 2;

[0058] n is selected from 1, 2, 3, 4, or 5;

[0059] R5 and R6 are each independently selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, perfluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, monofluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, or 2,2,2-trifluoroethylthio.

[0060] It may be a stereoisomer of a compound of general formula I;

[0061] Salts formed by compounds of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

[0062] Salts formed by the stereoisomer of a compound of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

[0063] In the definitions of general formula compounds given above, the terms used in the compilation generally represent the following substituents:

[0064] Halogens: refer to fluorine, chlorine, bromine or iodine.

[0065] Alkyl: Straight-chain or branched alkyl, such as methyl, ethyl, n-propyl, isopropyl or different butyl, pentyl or hexyl isomers.

[0066] Halogenated alkyl groups: straight-chain or branched alkyl groups in which hydrogen atoms may be partially or completely replaced by halogens, such as monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, perfluoroethyl, 1,1,1,3,3,3-hexafluoropropane-2-yl, etc.

[0067] Cycloalkyl: substituted or unsubstituted cyclic alkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; substituents such as methyl, halogen, etc.

[0068] Alkoxy: Straight-chain or branched alkyl groups, attached to the structure by oxygen atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, or tert-butoxy.

[0069] Halogenated alkoxy groups: straight-chain or branched alkoxy groups in which the hydrogen atoms may be partially or completely replaced by halogens, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, or 2,2,2-trifluoroethoxy.

[0070] Alkylthio group: a straight-chain or branched alkyl group that is attached to the structure via a sulfur atom bond, such as methylthio or ethylthio.

[0071] Halogenated alkylthio groups: straight-chain or branched alkylthio groups, in which the hydrogen atoms on these alkylthio groups may be partially or completely replaced by halogens, such as difluoromethylthio, trifluoromethylthio, or 2,2,2-trifluoroethylthio.

[0072] Alkyl carbonyl: Alkyl groups are attached to the structure via carbonyl groups, such as methyl carbonyl (CH3CO-), ethyl carbonyl (CH3CH2CO-), n-propyl carbonyl (CH3CH2CH2CO-), isopropyl carbonyl ((CH3)2CHCO-), n-butyl carbonyl (CH3CH2CH2CH2CO-), isobutyl carbonyl (CH3CH(CH3)2CO-), sec-butyl carbonyl (CH3CH2CH(CH3)CO-) or tert-butyl carbonyl ((CH3)3CCO-), etc.

[0073] Alkoxycarbonyl: Alkyl-O-CO-, such as methoxycarbonyl (CH3OCO-), ethoxycarbonyl (CH3CH2OCO-), n-propoxycarbonyl (CH3CH2CH2OCO-), isopropoxycarbonyl ((CH3)2CHOCO-), n-butoxycarbonyl (CH3CH2CH2CH2OCO-), isobutoxycarbonyl (CH3CH(CH3)2OCO-), sec-butoxycarbonyl (CH3CH2CH(CH3)OCO-) or tert-butoxycarbonyl ((CH3)3COCO-), etc.

[0074] Alkoxyalkyl: alkyl-O-alkyl-, such as CH3OCH2-, CH3CH2OCH2-, CH3CH2CH2OCH2-, (CH3)2CHOCH2-, CH3CH2CH2CH2OCH2-, (CH3)3COCH2-, CH3OCH2CH2-, CH3CH2OCH2CH2-, CH3CH2CH2OCH2CH2-, or CH3CH2CH2CH2OCH2CH2-, etc.

[0075] Alkyl carbonyloxyalkyl: alkyl-CO-O-alkyl-, for example, methyl carbonyloxymethyl Ethyl carbonyloxymethyl methylcarbonyloxyethyl Ethyl carbonyloxyethyl wait.

[0076] Alkoxycarbonylalkylcarbonyl: alkyl-O-CO-alkyl-CO-, for example, methoxycarbonylmethylcarbonyl ethoxycarbonylmethylcarbonyl or tert-butoxycarbonyl ethyl carbonyl wait.

[0077] benzyl:

[0078] Phenyl carbonyl:

[0079] Some of the compounds of general formula I in this invention are shown below, but this invention is by no means limited to these compounds.

[0080] When Q is selected from Q1, the compound of general formula I is selected from the compound of general formula IA, and the compounds of general formula IA are shown in Table 1.

[0081] In general formula IA, when R1 = F, R2 = Cl and X = O, R3 is a different substituent (see Table 1), and the compounds are numbered 1.1-1.991.

[0082] Table 1

[0083] In general formula IA, when R1 = F, R2 = Cl and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 2.1-2.991, which correspond to 1.1-1.991 in Table 1.

[0084] In general formula IA, when R1 = F, R2 = F and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 3.1-3.991, which correspond to 1.1-1.991 in Table 1.

[0085] In general formula IA, when R1 = F, R2 = F and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 4.1-4.991, which correspond to 1.1-1.991 in Table 1.

[0086] In general formula IA, when R1 = F, R2 = Br and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 5.1-5.991, which correspond to 1.1-1.991 in Table 1.

[0087] In general formula IA, when R1 = F, R2 = Br and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 6.1-6.991, which correspond to 1.1-1.991 in Table 1.

[0088] In general formula IA, when R1 = F, R2 = I and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 7.1-7.991, which correspond to 1.1-1.991 in Table 1.

[0089] In general formula IA, when R1 = F, R2 = I and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 8.1-8.991, which correspond to 1.1-1.991 in Table 1.

[0090] In general formula IA, when R1 = F, R2 = CN and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 9.1-9.991, which correspond to 1.1-1.991 in Table 1.

[0091] In general formula IA, when R1 = F, R2 = CN and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 10.1-10.991, corresponding to 1.1-1.991 in Table 1.

[0092] In general formula IA, when R1 = H, R2 = Cl and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 11.1-11.991, corresponding to 1.1-1.991 in Table 1.

[0093] In general formula IA, when R1 = H, R2 = Cl and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 12.1-12.991, corresponding to 1.1-1.991 in Table 1.

[0094] In general formula IA, when R1 = H, R2 = Br and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 13.1-13.991, corresponding to 1.1-1.991 in Table 1.

[0095] In general formula IA, when R1 = H, R2 = Br and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 14.1-14.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0096] In general formula IA, when R1 = H, R2 = F and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 15.1-15.991, corresponding to 1.1-1.991 in Table 1.

[0097] In general formula IA, when R1 = H, R2 = F and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 16.1-16.991, corresponding to 1.1-1.991 in Table 1.

[0098] In general formula IA, when R1 = H, R2 = I and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 17.1-17.991, corresponding to 1.1-1.991 in Table 1.

[0099] In general formula IA, when R1 = H, R2 = I and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 18.1-18.991, corresponding to 1.1-1.991 in Table 1.

[0100] In general formula IA, when R1 = H, R2 = CN and X = O, the substituent R3 is consistent with Table 1, representing compounds numbered 19.1-19.991, corresponding to 1.1-1.991 in Table 1.

[0101] In general formula IA, when R1 = H, R2 = CN and X = S, the substituent R3 is consistent with Table 1, representing compounds numbered 20.1-20.991, corresponding to 1.1-1.991 in Table 1 respectively.

[0102] When Q is selected from Q2, the compound of general formula I is selected from the compound of general formula IB:

[0103] In general formula IB, when R1 = F, R2 = Cl, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 21.1-21.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0104] In general formula IB, when R1 = F, R2 = Cl, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 22.1-22.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0105] In general formula IB, when R1 = F, R2 = F, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 23.1-23.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0106] In general formula IB, when R1 = F, R2 = F, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 24.1-24.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0107] In general formula IB, when R1 = F, R2 = Br, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 25.1-25.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0108] In general formula IB, when R1 = F, R2 = Br, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 26.1-26.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0109] In general formula IB, when R1 = F, R2 = I, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 27.1-27.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0110] In general formula IB, when R1 = F, R2 = I, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 28.1-28.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0111] In general formula IB, when R1 = F, R2 = CN, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 29.1-29.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0112] In general formula IB, when R1 = F, R2 = CN, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 30.1-30.991, corresponding to 1.1-1.991 in Table 1 respectively.

[0113] In general formula IB, when R1 = H, R2 = Cl, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 31.1-31.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0114] In general formula IB, when R1 = H, R2 = Cl, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 32.1-32.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0115] In general formula IB, when R1 = H, R2 = Br, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 33.1-33.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0116] In general formula IB, when R1 = H, R2 = Br, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 34.1-34.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0117] In general formula IB, when R1 = H, R2 = F, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 35.1-35.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0118] In general formula IB, when R1 = H, R2 = F, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 36.1-36.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0119] In general formula IB, when R1 = H, R2 = I, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 37.1-37.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0120] In general formula IB, when R1 = H, R2 = I, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 38.1-38.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0121] In general formula IB, when R1 = H, R2 = CN, m = 0 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 39.1-39.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0122] In general formula IB, when R1 = H, R2 = CN, m = 0 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 40.1-40.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0123] In general formula IB, when R1 = F, R2 = Cl, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 41.1-41.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0124] In general formula IB, when R1 = F, R2 = Cl, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 42.1-42.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0125] In general formula IB, when R1 = F, R2 = F, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 43.1-43.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0126] In general formula IB, when R1 = F, R2 = F, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 44.1-44.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0127] In general formula IB, when R1 = F, R2 = Br, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 45.1-45.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0128] In general formula IB, when R1 = F, R2 = Br, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 46.1-46.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0129] In general formula IB, when R1 = F, R2 = I, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 47.1-47.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0130] In general formula IB, when R1 = F, R2 = I, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 48.1-48.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0131] In general formula IB, when R1 = F, R2 = CN, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 49.1-49.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0132] In general formula IB, when R1 = F, R2 = CN, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 50.1-50.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0133] In general formula IB, when R1 = H, R2 = Cl, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 51.1-51.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0134] In general formula IB, when R1 = H, R2 = Cl, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 52.1-52.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0135] In general formula IB, when R1 = H, R2 = Br, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 53.1-53.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0136] In general formula IB, when R1 = H, R2 = Br, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 54.1-54.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0137] In general formula IB, when R1 = H, R2 = F, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 55.1-55.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0138] In general formula IB, when R1 = H, R2 = F, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 56.1-56.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0139] In general formula IB, when R1 = H, R2 = I, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 57.1-57.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0140] In general formula IB, when R1 = H, R2 = I, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 58.1-58.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0141] In general formula IB, when R1 = H, R2 = CN, m = 1 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 59.1-59.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0142] In general formula IB, when R1 = H, R2 = CN, m = 1 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 60.1-60.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0143] In general formula IB, when R1 = F, R2 = Cl, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 61.1-61.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0144] In general formula IB, when R1 = F, R2 = Cl, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 62.1-62.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0145] In general formula IB, when R1 = F, R2 = F, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 63.1-63.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0146] In general formula IB, when R1 = F, R2 = F, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 64.1-64.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0147] In general formula IB, when R1 = F, R2 = Br, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 65.1-65.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0148] In general formula IB, when R1 = F, R2 = Br, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 66.1-66.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0149] In general formula IB, when R1 = F, R2 = I, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 67.1-67.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0150] In general formula IB, when R1 = F, R2 = I, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 68.1-68.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0151] In general formula IB, when R1 = F, R2 = CN, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 69.1-69.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0152] In general formula IB, when R1 = F, R2 = CN, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 70.1-70.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0153] In general formula IB, when R1 = H, R2 = Cl, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 71.1-71.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0154] In general formula IB, when R1 = H, R2 = Cl, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 72.1-72.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0155] In general formula IB, when R1 = H, R2 = Br, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 73.1-73.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0156] In general formula IB, when R1 = H, R2 = Br, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 74.1-74.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0157] In general formula IB, when R1 = H, R2 = F, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 75.1-75.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0158] In general formula IB, when R1 = H, R2 = F, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 76.1-76.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0159] In general formula IB, when R1 = H, R2 = I, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 77.1-77.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0160] In general formula IB, when R1 = H, R2 = I, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 78.1-78.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0161] In general formula IB, when R1 = H, R2 = CN, m = 2 and X = O, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 79.1-79.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0162] In general formula IB, when R1 = H, R2 = CN, m = 2 and X = S, the substituent R4 is the same as R3 in Table 1, representing compounds numbered 80.1-80.991, which correspond to 1.1-1.991 in Table 1 respectively.

[0163] When Q is selected from Q3, the compound of general formula I is selected from the compound of general formula IC:

[0164] In the general formula IC, when R1 = F, R2 = Cl and X = 0, (R5) n The different substituents are shown in Table 2, and the compounds are numbered 81.1-81.311.

[0165] Table 2

[0166] In the general formula IC, when R1 = F, R2 = Cl and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 82.1-82.311, corresponding to 81.1-81.311 in Table 2.

[0167] In the general formula IC, when R1 = F, R2 = F and X = 0, the substituent (R5) n Consistent with Table 2, the compounds are numbered 83.1-83.311, corresponding to 81.1-81.311 in Table 2.

[0168] In the general formula IC, when R1 = F, R2 = F and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 84.1-84.311, corresponding to 81.1-81.311 in Table 2.

[0169] In the general formula IC, when R1 = F, R2 = Br and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 85.1-85.311, corresponding to 81.1-81.311 in Table 2.

[0170] In the general formula IC, when R1 = F, R2 = Br and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 86.1-86.311, corresponding to 81.1-81.311 in Table 2.

[0171] In the general formula IC, when R1 = F, R2 = I and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 87.1-87.311, corresponding to 81.1-81.311 in Table 2.

[0172] In the general formula IC, when R1 = F, R2 = I and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 88.1-88.311, corresponding to 81.1-81.311 in Table 2.

[0173] In the general formula IC, when R1 = F, R2 = CN and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 89.1-89.311, corresponding to 81.1-81.311 in Table 2.

[0174] In the general formula IC, when R1 = F, R2 = CN and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 90.1-90.311, corresponding to 81.1-81.311 in Table 2.

[0175] In the general formula IC, when R1 = H, R2 = Cl and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 91.1-91.311, corresponding to 81.1-81.311 in Table 2.

[0176] In the general formula IC, when R1 = H, R2 = Cl and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 92.1-92.311, corresponding to 81.1-81.311 in Table 2.

[0177] In the general formula IC, when R1 = H, R2 = F and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 93.1-93.311, corresponding to 81.1-81.311 in Table 2.

[0178] In the general formula IC, when R1 = H, R2 = F and X = S, the substituent (R5) nConsistent with Table 2, the compounds are numbered 94.1-94.311, corresponding to 81.1-81.311 in Table 2.

[0179] In the general formula IC, when R1 = H, R2 = Br and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 95.1-95.311, corresponding to 81.1-81.311 in Table 2.

[0180] In the general formula IC, when R1 = H, R2 = Br and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 96.1-96.311, corresponding to 81.1-81.311 in Table 2.

[0181] In the general formula IC, when R1 = H, R2 = I and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 97.1-97.311, corresponding to 81.1-81.311 in Table 2.

[0182] In the general formula IC, when R1 = H, R2 = I and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 98.1-98.311, corresponding to 81.1-81.311 in Table 2.

[0183] In the general formula IC, when R1 = H, R2 = CN and X = O, the substituent (R5) n Consistent with Table 2, the compounds are numbered 99.1-99.311, corresponding to 81.1-81.311 in Table 2.

[0184] In the general formula IC, when R1 = H, R2 = CN and X = S, the substituent (R5) n Consistent with Table 2, the compounds are numbered 100.1-100.311, corresponding to 81.1-81.311 in Table 2.

[0185] The present invention also provides a method for preparing the above-mentioned uracil compounds (i.e., compounds of general formula I, including compounds of general formula IA, general formula IB, and general formula IC; wherein compounds of general formula IB include compounds of general formula IB-1, general formula IB-2, and general formula IB-3), as follows (unless otherwise specified, each group in the formula is defined as above, and LG = Cl, Br, or I):

[0186] Using conventional methods, intermediates of general formula VII and general formula II can be reacted in a suitable solvent at a temperature ranging from 0°C to the solvent's boiling point for 0.5–48 hours to prepare general formula IA. Similarly, intermediates of general formula VII and general formula III can be reacted in a suitable solvent at a temperature ranging from 0°C to the solvent's boiling point for 0.5–48 hours to prepare general formula IB-1. Likewise, intermediates of general formula VII and general formula IV can be reacted in a suitable solvent at a temperature ranging from 0°C to the solvent's boiling point for 0.5–48 hours to prepare general formula IB-2. Similarly, intermediates of general formula VII and general formula V can be reacted in a suitable solvent at a temperature ranging from 0°C to the solvent's boiling point for 0.5–48 hours to prepare general formula IB-3. Similarly, intermediates of general formula VII and general formula VI can be reacted in a suitable solvent at temperatures ranging from 0°C to the solvent's boiling point for 0.5–48 hours to yield compound of general formula IC. Suitable solvents can be the same or different and include alcohols (e.g., methanol, ethanol), aromatic hydrocarbons (e.g., benzene, toluene, xylene), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone), halogenated hydrocarbons (e.g., dichloromethane, chloroform, carbon tetrachloride), esters (e.g., methyl acetate, ethyl acetate), ethers (e.g., tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane), polar solvents (e.g., water, acetonitrile, dioxane, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide), or mixtures of the above solvents. The reaction can be carried out in the presence or absence of a base; the presence of a base accelerates the reaction. The base can be selected from alkali metal hydrides, such as sodium hydride, lithium hydride, or sodium amide; alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide; alkali metal carbonates, such as sodium carbonate or potassium carbonate; and organic bases, such as pyridine, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole, or diisopropylethylamine. The reaction temperature can range from -10°C to the boiling point of the suitable solvent used in the reaction, typically 0–100°C. The reaction time is from 30 minutes to 20 hours, typically 1–10 hours.

[0187] Furthermore, compounds of general formula IB-1 react with suitable oxidizing agents to yield the corresponding sulfoxide compounds, i.e., compounds of general formula IB-2. Similarly, compounds of general formula IB-1 react with suitable oxidizing agents to yield the corresponding sulfone compounds, i.e., compounds of general formula IB-3. Suitable oxidizing agents include m-chloroperoxybenzoic acid, hydrogen peroxide, or sodium (meta)periodate, etc. Reaction solvents are selected from water, methanol, ethanol, diethyl ether, dichloromethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, DMF, tetrahydrofuran, or dioxane, etc. The reaction is usually carried out at a temperature of 0-100°C. The reaction time is usually from 10 minutes to 48 hours.

[0188] Intermediate compounds of general formula VII can be prepared by known methods, such as those reported in WO2003014109, WO2021013799, EP1122244, CN1204137, CN1636981, CN1328261, CN1537110, CN1238352, and CN114401956. Compounds of general formulas II, III, IV, V, and VI are generally commercially available or can be prepared by conventional methods.

[0189] The compound of general formula I of this invention can effectively control weeds such as barnyard grass, zinnia, foxtail, and velvetleaf, achieving good results even at low doses. It exhibits a certain degree of safety in wheat, corn, and rice, and can be used as a herbicide in agriculture. Therefore, this invention also includes the use of the compound of general formula I for weed control.

[0190] The present invention also provides a herbicidal composition having a compound of general formula I as the active ingredient, wherein the active ingredient in the composition comprises 0.1-99% by weight. Therefore, the present invention also includes the use of this composition for controlling weeds.

[0191] The compositions of the present invention can be prepared into corresponding dosage forms using methods known to those skilled in the art. The active ingredient may contain a single compound or a mixture of several compounds of the present invention.

[0192] The carrier system in the compositions of the present invention is a substance that, after being formulated with the active ingredients, is easily applied to the site to be treated, such as a plant, seed, or soil; or is conducive to storage, transport, or handling. The carrier can be solid or liquid, including substances that are typically gaseous but have been compressed into a liquid; carriers commonly used in the formulation of herbicidal compositions can be used.

[0193] Suitable solid carriers include natural and synthetic clays and silicates (e.g., diatomaceous earth, talc, magnesia, aluminum silicate (kaolin), montmorillonite, and mica), calcium carbonate, calcium sulfate, ammonium sulfate, synthetic silica, synthetic calcium silicate, synthetic aluminum silicate, natural resins, synthetic resins (natural resins, synthetic resins such as benzofuran resins, polyvinyl chloride and styrene polymers and copolymers), solid polychlorinated phenols, bitumen, or waxes (e.g., beeswax, paraffin).

[0194] Suitable liquid carriers include one or a mixture of several of the following: water, alcohols (such as isopropanol and ethanol), ketones (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, cyclohexyl ketone), ethers, aromatics (such as benzene, toluene, xylene), petroleum fractions (such as kerosene and mineral oil), and chlorinated hydrocarbons (such as carbon tetrachloride, perchloroethylene, and trichloroethylene).

[0195] The composition is typically processed into a concentrated form for transport, and then diluted by the user before application. The presence of a small amount of surfactant carrier facilitates the dilution process. Thus, at least one carrier in the composition according to the invention is preferably a surfactant. For example, the composition may contain at least two carriers, at least one of which is a surfactant.

[0196] Surfactants can be emulsifiers, dispersants, or wetting agents; they can be nonionic or ionic. Examples of suitable surfactants include sodium or calcium salts of polyacrylic acid and lignin sulfonate; condensates of fatty acids or fatty amines or amides containing at least 12 carbon atoms with ethylene oxide and / or propylene oxide; glycols, sorbitol, sucrose, or pentaerythritol fatty acid esters and condensates of these esters with ethylene oxide and / or propylene oxide; condensates of fatty alcohols or alkylphenols such as p-octylphenol or p-octylcresol with ethylene oxide and / or propylene oxide; sulfates and sulfonates of these condensate products; alkali metal or alkaline earth metal salts of sulfuric acid or sulfonate esters containing at least 10 carbon atoms, preferably sodium salts, such as sodium lauryl sulfate, sodium secondary alkyl sulfate, sodium sulfonated castor oil, and sodium alkyl aryl sulfonates, such as sodium dodecylbenzene sulfonate.

[0197] Examples of compositions of the present invention are wettable powders, powders, granules, aqueous solutions, emulsifiable concentrates, emulsions, aerosols, and smoke agents. Wettable powders typically contain 25-75% by weight of the active ingredient and, in addition to a solid inert carrier, typically contain 3-10% by weight of a dispersant, and, if necessary, 0-10% by weight of a stabilizer and / or other additives such as penetrants or binders. Powders are typically powder concentrates having a similar composition to wettable powders but without a dispersant, further diluted with a solid carrier to obtain a composition typically containing 0.5-10% by weight of the active ingredient. Granules are typically prepared to have a size of 10 to 100 mesh (1.676-0.152 mm) and can be prepared using agglomeration or injection techniques. Granules typically contain 0.5-75% by weight of the active ingredient and 0-10% by weight of additives (additives such as stabilizers, surfactants, or sustained-release modifiers). Emulsifiable concentrates, in addition to solvents, typically contain a co-solvent, 1-50% w / v of active ingredient, 2-20% w / v of emulsifier, and 0-20% w / v of other additives (such as stabilizers, penetrants, or corrosion inhibitors), when required. Suspension concentrates typically contain 10-75% by weight of active ingredient, 0.5-15% by weight of dispersant, and 0.1-10% by weight of other additives (such as defoamers, corrosion inhibitors, stabilizers, penetrants, and binders).

[0198] Water-dispersants and emulsions, such as compositions obtained by diluting wettable powders or concentrates according to the invention with water, are also included within the scope of this invention. The emulsions may be of the water-in-oil or oil-in-water type.

[0199] By adding one or more other herbicides to the composition, it can achieve a broader spectrum of activity than the compound of general formula I alone. Furthermore, other herbicides can enhance the herbicidal activity of the compound of general formula I. The compound of general formula I can also be mixed with other herbicides. The content of the active ingredient in the mixture varies widely, generally ranging from 1% to 95%, with a more suitable content of 5% to 60%.

[0200] The composition using the compound of general formula I of the present invention as the active component can effectively control weeds. This type of compound can effectively control weeds such as barnyard grass, velvetleaf, foxtail grass, and zinnia as herbicides, and has a certain degree of safety for wheat, corn, and rice. It can be used as a herbicide in agriculture.

[0201] This invention does not impose any particular limitations on the method for preparing the pesticide herbicide. Those skilled in the art can use conventional preparation methods in the pesticide field to prepare the corresponding reagent.

[0202] The pesticides and herbicides described in this invention include, but are not limited to, those applied to crops by methods such as spraying.

[0203] It should be clearly stated that various modifications and alterations can be made within the scope defined by the claims of this invention. Detailed Implementation

[0204] The following specific embodiments are used to further illustrate the present invention, but the present invention is by no means limited to these examples. (Unless otherwise noted, all raw materials used are commercially available.)

[0205] Synthesis Examples

[0206] Following the synthetic route described above, compounds of general formula I of this invention can be prepared by using different starting materials, as further described in detail below:

[0207] Example 1: Preparation of compound 1.1

[0208] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.09 g (0.72 mmol) of bromomethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.16 g of a white solid, which was compound 1.1. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.98(m,1H),7.89-7.86(m,1H),7.51-7.48(m,1H),7.13-7.09(m,2H),6 .54(s,1H),5.22(s,2H),5.00-4.94(m,2H),3.37(s,3H),3.28(s,3H).LC-MS(m / z,ESI):534.07(M+H) + .

[0209] Example 2: Preparation of compound 1.2

[0210] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.07 g (0.74 mmol) of chloromethyl ethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of a white solid, which was compound 1.2. 1H NMR(600MHz,DMSO-d6)δ7.99(dd,1H),7.88(d,1H),7.51(d,1H),7.15-7.08(m,2H),6.55(s,1H), 5.26(s,2H),4.96(d,2H),3.52(q,2H),3.38(s,3H),1.07(t,3H).LC-MS(m / z,ESI):548.12(M+H) + .

[0211] Example 3: Preparation of compound 1.4

[0212] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.08 g (0.74 mmol) of chloromethyl isopropyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of a white solid, which was compound 1.4. 1 H NMR(600MHz,DMSO-d6)δ7.98(dd,1H),7.87(d,1H),7.50(dd,1H),7.12-7.08(m,2H),6.54(s,1H),5. 27(s,2H),4.94(d,2H),3.74-3.71(m,1H),3.37(s,3H),1.04(d,6H).LC-MS(m / z,ESI):562.12(M+H) + .

[0213] Example 4: Preparation of compound 1.23

[0214] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.08 g (0.74 mmol) of methyl chloride acetate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of a white solid, which was compound 1.23. 1 H NMR(600MHz,DMSO-d6)δ7.99(dd,1H),7.87(d,1H),7.50(dd,1H),7.14-7.11(m,1H),7.06(d,1H),6. 54(s,1H),5.67(d,2H),5.00-4.94(m,2H),3.37(s,3H),2.03(s,3H).LC-MS(m / z,ESI):562.08(M+H) + .

[0215] Example 5: Preparation of compound 1.25

[0216] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the flask, followed by 0.10 g (0.74 mmol) of methyl butyrate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of an oily substance, which was compound 1.25. 1H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.87(d,1H),7.51(dd,1H),7.12(dd,1H),7.03(d,1H),6.54(s,1H),5.71-5.65 (m,2H),4.97(s,2H),3.37(s,3H),2.28-2.26(m,2H),1.52-1.44(m,2H),0.85(t,3H).LC-MS(m / z,ESI):590.13(M+H) + .

[0217] Example 6: Preparation of compound 1.30

[0218] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.11 g (0.74 mmol) of methyl tert-pentanoate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.12 g of an oily substance, which was compound 1.30. 1 H NMR(600MHz,DMSO-d6)δ7.95(dd,1H),7.88(d,1H),7.52(d,1H),7.12(dd,1H),7.03(d,1H),6.55 (s,1H),5.71-5.68(m,2H),4.98(s,2H),3.38(s,3H),1.10(s,9H).LC-MS(m / z,ESI):604.18(M+H) + .

[0219] Example 7: Preparation of compound 1.34

[0220] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.11 g (0.74 mmol) of isopropyl chloromethyl carbonate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.14 g of a white solid, which was compound 1.34. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.87(d,1H),7.53(dd,1H),7.13-7.10(m,1H),6.99(d,1H),6.54(s,1H) ,5.65(d,2H),5.00-4.97(m,2H),4.71-4.67(m,1H),3.37(s,3H),1.20(d,6H).LC-MS(m / z,ESI):606.22(M+H) + .

[0221] Example 8: Preparation of compound 1.45

[0222] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.09 g (0.74 mmol) of 2-methoxyethoxymethyl chloride. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.15 g of a white solid, which was compound 1.45. 1H NMR(600MHz,DMSO-d6)δ7.98(dd,1H),7.87(d,1H),7.51(dd,1H),7.14-7.07(m,2H),6.54(s,1H),5.27(s,2H ),4.95(d,2H),3.60-3.56(m,2H),3.42-3.38(m,2H),3.37(s,3H)3.21(s,3H).LC-MS(m / z,ESI):578.15(M+H) + .

[0223] Example 9: Preparation of compound 1.368

[0224] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the flask, followed by 0.12 g (0.77 mmol) of benzylchloromethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.17 g of an oily substance, which was compound 1.368. 1 H NMR (600MHz, DMSO-d6) δ7.99(dd,1H),7.87(d,1H),7.52(dd,1H),7.37-7.30(m,3H),7.27-7.24(m,2H),7.13-7. 08(m,2H),6.50(s,1H),5.36(s,2H),4.99-4.95(m,2H),4.53(s,2H),3.34(s,3H).LC-MS(m / z,ESI):610.17(M+H) + .

[0225] Example 10: Preparation of compound 1.680

[0226] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.12 g (0.77 mmol) of chloromethyl benzoate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.17 g of an oily substance, which was compound 1.680. 1 H NMR(600MHz,DMSO-d6)δ7.94-7.90(m,2H),7.86(d,1H),7.79(dd,1H),7.74-7.69(m,1H),7.58-7.54(m,2H),7.47(dd,1H) ,7.05(d,1H),7.01-6.98(m,1H),6.52(s,1H),5.97-5.93(m,2H),5.00(s,2H),3.36(s,3H).LC-MS(m / z,ESI):624.15(M+H) + .

[0227] Example 11: Preparation of compound 5.1

[0228] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.08 g (0.68 mmol) of bromomethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.16 g of a white solid, which was compound 5.1. 1H NMR(600MHz,DMSO-d6)δ8.00-7.92(m,2H),7.47(dd,1H),7.13-7.04(m,2H),6.54(s,1 H),5.22(s,2H),4.97(d,2H),3.37(s,3H),3.28(s,3H).LC-MS(m / z,ESI):578.05(M+H) + .

[0229] Example 12: Preparation of compound 5.2

[0230] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.06 g (0.68 mmol) of chloromethyl ethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 5.2. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.96(m,2H),7.48(dd,1H),7.12-7.09(m,1H),7.05(d,1H),6.54(s,1 H),5.25(s,2H),4.95(d,2H),3.51(q,2H),3.37(s,3H),1.07(t,3H).LC-MS(m / z,ESI):592.10(M+H) + .

[0231] Example 13: Preparation of compound 5.4

[0232] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.07 g (0.68 mmol) of chloromethyl isopropyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of a white solid, which was compound 5.4. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.93(m,2H),7.48(dd,1H),7.11(dd,1H),7.04(d,1H),6.54(s,1H),5. 27(s,2H),4.94(d,2H),3.76-3.70(m,1H),3.37(s,3H),1.04(d,6H).LC-MS(m / z,ESI):606.15(M+H) + .

[0233] Example 14: Preparation of compound 5.23

[0234] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.07 g (0.68 mmol) of methyl chloride acetate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.16 g of an oily substance, which was compound 5.23. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.96(m,2H),7.48(dd,1H),7.13-7.10(m,1H),7.01(d,1H),6.5 4(s,1H),5.67(s,2H),4.97(s,2H),3.37(s,3H),2.03(s,3H).LC-MS(m / z,ESI):606.10(M+H)+ .

[0235] Example 15: Preparation of compound 5.25

[0236] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.09 g (0.68 mmol) of methyl butyrate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of an oily substance, which was compound 5.25. 1 H NMR(600MHz,DMSO-d6)δ7.99-7.96(m,2H),7.50-7.48(m,1H),7.13-7.10(m,1H),6.98(d,1H),6.53(s,1H),5.69-5.6 6(m,2H),4.97(s,2H),3.37(s,3H),2.29-2.26(m,2H),1.51-1.45(m,2H),0.85(t,3H).LC-MS(m / z,ESI):634.23(M+H) + .

[0237] Example 16: Preparation of compound 5.30

[0238] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.10 g (0.68 mmol) of methyl tert-pentanoate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.16 g of an oily substance, which was compound 5.30. 1H NMR(600MHz,DMSO-d6)δ7.98(d,1H),7.95-7.93(m,1H),7.50-7.48(m,1H),7.13-7.10(m,1H),6.98(d,1H ),6.54(s,1H),5.71-5.67(m,2H),4.97(s,2H),3.37(s,3H),1.09(s,9H).LC-MS(m / z,ESI):648.23(M+H) + .

[0239] Example 17: Preparation of compound 5.34

[0240] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the flask, followed by 0.10 g (0.68 mmol) of isopropyl chloromethyl carbonate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of an oily substance, which was compound 5.34. 1 H NMR(600MHz,DMSO-d6)δ8.01-7.93(m,2H),7.51(dd,1H),7.14-7.10(m,1H),6.94(d,1H),6.54(s,1H), 5.65(d,2H),4.99(s,2H),4.71-4.66(m,1H),3.37(s,3H),1.20(d,6H).LC-MS(m / z,ESI):650.14(M+H) + .

[0241] Example 18: Preparation of compound 5.45

[0242] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.08 g (0.68 mmol) of 2-methoxyethoxymethyl chloride. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.17 g of an oily substance, which was compound 5.45. 1 H NMR(600MHz,DMSO-d6)δ7.99-7.96(m,2H),7.48(dd,1H),7.12-7.10(m,1H),7.05(d,1H),6.54(s,1H),5.27(s,2 H),4.95(d,2H),3.59-3.57(m,2H),3.40-3.38(m,2H),3.37(s,3H),3.21(s,3H).LC-MS(m / z,ESI):622.17(M+H) + .

[0243] Example 19: Preparation of compound 5.368

[0244] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.10 g (0.68 mmol) of benzylchloromethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.20 g of an oily substance, which was compound 5.368. 1H NMR(600MHz,DMSO-d6)δ8.05-7.89(m,2H),7.51(dd,1H),7.40-7.28(m,3H),7.30-7.21(m,2H),7.15-7.08(m,1H ),7.05(d,1H),6.50(s,1H),5.36(s,2H),4.98(s,2H),4.54(s,2H),3.34(s,3H).LC-MS(m / z,ESI):654.27(M+H) + .

[0245] Example 20: Preparation of compound 5.680

[0246] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the flask, followed by 0.11 g (0.68 mmol) of chloromethyl benzoate. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.20 g of an oily substance, which was compound 5.680. 1 H NMR(600MHz,DMSO-d6)δ7.97(d,1H),7.94-7.91(m,2H),7.78(dd,1H),7.73-7.70(m,1H),7.58-7.54(m,2H),7.46-7.4 4(m,1H),7.02-6.97(m,2H),6.52(s,1H),5.97-5.92(m,2H),5.00(s,2H),3.36(s,3H).LC-MS(m / z,ESI):668.23(M+H) + .

[0247] Example 21: Preparation of compound 7.1

[0248] 0.30 g (0.52 mmol) of 2-((3-(2-iodo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.14 g (1.03 mmol) of potassium carbonate was added to the reaction flask, followed by 0.08 g (0.62 mmol) of bromomethyl ether. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of an oily substance, which was compound 7.1. 1 H NMR(600MHz,DMSO-d6)δ8.05(d,1H),7.98(dd,1H),7.42(dd,1H),7.11-7.08(m,1H),6.95(d,1H) ,6.53(s,1H),5.23(s,2H),4.98(s,2H),3.37(s,3H),3.29(s,3H).LC-MS(m / z,ESI):626.17(M+H) + .

[0249] Example 22: Preparation of compound 7.45

[0250] 0.30 g (0.52 mmol) of 2-((3-(2-iodo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.14 g (1.03 mmol) of potassium carbonate was added to the reaction flask, followed by 0.07 g (0.62 mmol) of 2-methoxyethoxymethyl chloride. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of an oily substance, which was compound 7.45. 1H NMR(600MHz,DMSO-d6)δ8.05(d,1H),7.98(dd,1H),7.44(dd,1H),7.10(dd,1H),6.93(d,1H),6.53(s,1H),5.28(s ,2H),4.96(d,2H),3.61-3.57(m,2H),3.41-3.38(m,2H),3.37(s,3H),3.22(s,3H).LC-MS(m / z,ESI):670.25(M+H) + .

[0251] Example 23: Preparation of compound 21.1

[0252] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.07 g (0.72 mmol) of chloromethyl methyl sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.13 g of a white solid, which was compound 21.1. 1 H NMR(600MHz,DMSO-d6)δ8.02-7.97(m,1H),7.88(d,1H),7.53-7.47(m,1H),7.15-7.06(m,2H),6.5 5(s,1H),5.22(s,2H),5.02-4.95(m,2H),3.38(s,3H),2.10(s,3H).LC-MS(m / z,ESI):550.07(M+H) + .

[0253] Example 24: Preparation of compound 21.56

[0254] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.12 g (0.74 mmol) of chloromethylphenyl sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.21 g of an oily substance, which was compound 21.56. 1 H NMR(600MHz,DMSO-d6)δ7.94(dd,1H),7.87(d,1H),7.48(dd,1H),7.36-7.33(m,2H),7.32-7.26(m,3H) ,7.10-7.07(m,2H),6.53(s,1H),5.53(s,2H),4.97(d,2H),3.36(s,3H).LC-MS(m / z,ESI):612.14(M+H) + .

[0255] Example 25: Preparation of compound 21.62

[0256] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.74 mmol) of chloromethyl p-toluene sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.20 g of an oily substance, which was compound 21.62. 1H NMR(600MHz,DMSO-d6)δ7.95(dd,1H),7.87(d,1H),7.49(dd,1H),7.25-7.21(m,2H),7.13-7.06(m,4 H),6.53(s,1H),5.46(s,2H),4.96(s,2H),3.36(s,3H),2.27(s,3H).LC-MS(m / z,ESI):626.19(M+H) + .

[0257] Example 26: Preparation of compound 21.368

[0258] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.74 mmol) of benzylchloromethyl sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 21.368. 1 H NMR(600MHz,DMSO-d6)δ8.03-7.99(m,1H),7.89(d,1H),7.54-7.50(m,1H),7.34-7.31(m,2H),7.29-7.25(m,3H),7 .17-7.10(m,2H),6.53(s,1H),5.16(s,2H),4.95(s,2H),3.79(s,2H),3.36(s,3H).LC-MS(m / z,ESI):626.15(M+H) + .

[0259] Example 27: Preparation of compound 25.1

[0260] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.06 g (0.67 mmol) of chloromethyl methyl sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.17 g of an oily substance, which was compound 25.1. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.96(m,2H),7.47(dd,1H),7.11(dd,1H),7.07(d,1H),6.54( s,1H),5.22(s,2H),4.97(d,2H),3.37(s,3H),2.09(s,3H).LC-MS(m / z,ESI):594.06(M+H) + .

[0261] Example 28: Preparation of compound 25.56

[0262] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.11 g (0.67 mmol) of chloromethylphenyl sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.20 g of an oily substance, which was compound 25.56. 1 H NMR(600MHz,DMSO-d6)δ7.98(d,1H),7.93(dd,1H),7.46(dd,1H),7.36-7.26(m,5H),7.10-7.07(m,1 H),7.04(d,1H),6.53(s,1H),5.54(s,2H),4.98(d,2H),3.36(s,3H).LC-MS(m / z,ESI):656.16(M+H)+ .

[0263] Example 29: Preparation of compound 25.62

[0264] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.12 g (0.67 mmol) of chloromethyl p-toluene sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 25.62. 1 H NMR(600MHz,DMSO-d6)δ7.98(d,1H),7.95(dd,1H),7.48(dd,1H),7.26-7.22(m,2H),7.14-7.10(m,3H),7. 04(d,1H),6.54(s,1H),5.47(s,2H),4.97(s,2H),3.36(s,3H),2.28(s,3H).LC-MS(m / z,ESI):670.26(M+H) + .

[0265] Example 30: Preparation of compound 25.368

[0266] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.12 g (0.67 mmol) of benzyl chloride methyl sulfide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.21 g of an oily substance, which was compound 25.368. 1H NMR(600MHz,DMSO-d6)δ8.01-7.97(m,2H),7.49(dd,1H),7.33-7.30(m,2H),7.27-7.24(m,3H),7.13-7.11(m,1H ),7.08(d,1H),6.52(s,1H),5.15(d,2H),4.94(d,2H),3.78(s,2H),3.35(s,3H).LC-MS(m / z,ESI):670.19(M+H) + .

[0267] Example 31: Preparation of compound 61.56

[0268] 0.30 g (0.49 mmol) of (phenylthio)methyl 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetate (compound 21.56) was placed in a 25 mL round-bottom flask, and 5 mL of dichloromethane was added to dissolve and dilute it. After complete dissolution, the reaction solution was cooled to 0 °C and stirred for 30 minutes. Then, 0.25 g (1.47 mmol) of m-chloroperoxybenzoic acid was added to the above reaction flask, and stirring was started. After reacting at 0 °C for 1 hour, the mixture was moved to room temperature and the reaction was continued for 3 hours. TLC detection showed that the reaction had been completed. Saturated sodium thiosulfate aqueous solution and dichloromethane were added for extraction to separate the organic phase. The organic phase was washed successively with 10% sodium carbonate aqueous solution and saturated sodium chloride solution, dried with anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography to obtain 0.27 g of white solid, which is compound 61.56. 1 H NMR(600MHz,DMSO-d6)δ7.94(dd,1H),7.87(d,1H),7.86-7.82(m,2H),7.81-7.77(m,1H),7.67-7.63(m,2H),7.49(dd,1 H),7.14-7.11(m,1H),7.08(d,1H),6.54(s,1H),5.47(s,2H),4.99(s,2H),3.37(s,3H).LC-MS(m / z,ESI):644.23(M+H) + .

[0269] Example 32: Preparation of compound 61.62

[0270] 0.30 g (0.48 mmol) of (p-toluenethio)methyl 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dione-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetate (compound 21.62) was placed in a 25 mL round-bottom flask, and 5 mL of dichloromethane was added to dissolve and dilute it. After complete dissolution, the reaction solution was cooled to 0 °C and stirred for 30 minutes. Then, 0.25 g (1.44 mmol) of m-chloroperoxybenzoic acid was added to the above reaction flask, and stirring was started. After reacting at 0 °C for 1 hour, the mixture was moved to room temperature and the reaction was continued for 3 hours. TLC detection showed that the reaction had been completed. Saturated sodium thiosulfate aqueous solution and dichloromethane were added for extraction to separate the organic phase. The organic phase was washed successively with 10% sodium carbonate aqueous solution and saturated sodium chloride solution, dried with anhydrous magnesium sulfate, concentrated, and purified by silica gel column chromatography to obtain 0.25 g of oil, which is compound 61.62. 1 H NMR(600MHz,DMSO-d6)δ7.93(dd,1H),7.88(d,1H),7.72-7.69(m,2H),7.49(dd,1H),7.44(d,2H),7.14-7.11(m,1 H),7.08(d,1H),6.54(s,1H),5.42(d,2H),4.99(s,2H),3.37(s,3H),2.42(s,3H).LC-MS(m / z,ESI):658.25(M+H) + .

[0271] Example 33: Preparation of compound 81.1

[0272] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 2-fluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.13 g of a yellow solid, which was compound 81.1. 1H NMR(600MHz,DMSO-d6)δ7.94-7.92(m,1H),7.86(d,1H),7.49-7.45(m,1H),7.43-7.38(m,2H),7.23-7.19(m ,2H),7.12-7.08(m,2H),6.53(s,1H),5.20(s,2H),4.98(s,2H),3.36(s,3H).LC-MS(m / z,ESI):598.12(M+H) + .

[0273] Example 34: Preparation of compound 81.2

[0274] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 3-fluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of a yellow solid, which was compound 81.2. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.94(m,1H),7.86(d,1H),7.51-7.46(m,1H),7.43-7.36(m,1H),7.2 0-7.03(m,5H),6.52(s,1H),5.18(s,2H),5.02(s,2H),3.36(s,3H).LC-MS(m / z,ESI):598.06(M+H) + .

[0275] Example 35: Preparation of compound 81.3

[0276] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 4-fluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of an oily substance, which was compound 81.3. 1 H NMR(600MHz,DMSO-d6)δ7.96(dd,1H),7.86(d,1H),7.47(dd,1H),7.38-7.33(m,2H),7.20-7.16(m,2H) ,7.13-7.08(m,2H),6.53(s,1H),5.14(s,2H),4.98(d,2H),3.36(s,3H).LC-MS(m / z,ESI):598.14(M+H) + .

[0277] Example 36: Preparation of compound 81.4

[0278] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 2-methylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 81.4. 1H NMR(600MHz,DMSO-d6)δ7.94(dd,1H),7.85(d,1H),7.47(dd,1H),7.27-7.22(m,2H),7.19-7.15(m,2H),7.12- 7.08(m,2H),6.53(s,1H),5.15(s,2H),4.99(d,2H),3.36(s,3H),2.22(s,3H).LC-MS(m / z,ESI):594.19(M+H) + .

[0279] Example 37: Preparation of compound 81.5

[0280] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 3-methylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 81.5. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.49(dd,1H),7.24-7.21(m,1H),7.13-7.06(m,4H),7.04- 7.02(m,1H),6.52(s,1H),5.11(s,2H),4.99(d,2H),3.36(s,3H),2.27(s,3H).LC-MS(m / z,ESI):594.13(M+H) + .

[0281] Example 38: Preparation of compound 81.6

[0282] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 4-methylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.21 g of an oily substance, which was compound 81.6. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.48(dd,1H),7.19-7.13(m,4H),7.12-7.08(m,2 H),6.53(s,1H),5.10(s,2H),4.97(d,2H),3.36(s,3H),2.29(s,3H).LC-MS(m / z,ESI):594.18(M+H) + .

[0283] Example 39: Preparation of compound 81.10

[0284] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the flask, followed by 0.17 g (0.74 mmol) of 2-trifluoromethylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.20 g of an oily substance, which was compound 81.10. 1H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.76(d,1H),7.71-7.69(m,1H),7.62-7.55(m,2H),7.50-7.4 7(m,1H),7.13-7.09(m,2H),6.49(s,1H),5.31(s,2H),5.03(d,2H),3.35(s,3H).LC-MS(m / z,ESI):648.14(M+H) + .

[0285] Example 40: Preparation of compound 81.11

[0286] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.17 g (0.74 mmol) of 3-trifluoromethylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 81.11. 1 H NMR(600MHz,DMSO-d6)δ7.93(dd,1H),7.86(d,1H),7.70-7.66(m,1H),7.65-7.60(m,3H),7.49(dd,1H) ,7.12-7.08(m,2H),6.51(s,1H),5.26(s,2H),5.02(d,2H),3.35(s,3H).LC-MS(m / z,ESI):648.23(M+H) + .

[0287] Example 41: Preparation of compound 81.12

[0288] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.17 g (0.74 mmol) of 4-trifluoromethylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 81.12. 1 H NMR(600MHz,DMSO-d6)δ7.98(dd,1H),7.86(d,1H),7.72(d,2H),7.53-7.48(m,3H),7.13-7.1 0(m,2H),6.51(s,1H),5.27(s,2H),5.03(d,2H),3.35(s,3H).LC-MS(m / z,ESI):648.17(M+H) + .

[0289] Example 42: Preparation of compound 81.16

[0290] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 2-chlorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.21 g of an oily substance, which was compound 81.16. 1H NMR(600MHz,DMSO-d6)δ7.96-7.94(m,1H),7.86(d,1H),7.50-7.46(m,2H),7.45-7.42(m,1H),7.39-7.34(m ,2H),7.12-7.09(m,2H),6.52(s,1H),5.22(s,2H),5.02(d,2H),3.36(s,3H).LC-MS(m / z,ESI):614.10(M+H) + .

[0291] Example 43: Preparation of compound 81.17

[0292] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 3-chlorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.23 g of an oily substance, which was compound 81.17. 1 H NMR(600MHz,DMSO-d6)δ7.99-7.96(m,1H),7.88-7.85(m,1H),7.50-7.47(m,1H),7.44-7.30(m,3H),7.29-7.24 (m,1H),7.13-7.09(m,2H),6.52(s,1H),5.17(s,2H),5.01(d,2H),3.36(d,3H).LC-MS(m / z,ESI):614.10(M+H) + .

[0293] Example 44: Preparation of compound 81.18

[0294] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 4-chlorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of a brown solid, which was compound 81.18. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.97(m,1H),7.89-7.86(m,1H),7.50-7.48(m,1H),7.44-7.40(m,2H),7.35-7.31 (m,2H),7.13-7.10(m,2H),6.54(s,1H),5.16(s,2H),5.00(d,2H),3.37(d,3H).LC-MS(m / z,ESI):614.05(M+H) + .

[0295] Example 45: Preparation of compound 81.19

[0296] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 2-cyanobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.20 g of a white solid, which was compound 81.19. 1H NMR(600MHz,DMSO-d6)δ7.91(dd,1H),7.88-7.84(m,2H),7.75-7.71(m,1H),7.58-7.54(m,2H),7.48(dd,1 H),7.12-7.08(m,2H),6.52(s,1H),5.31(s,2H),5.00(d,2H),3.36(s,3H).LC-MS(m / z,ESI):605.13(M+H) + .

[0297] Example 46: Preparation of compound 81.20

[0298] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 3-cyanobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.18 g of a white solid, which was compound 81.20. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.87(d,1H),7.80(d,1H),7.74-7.73(m,1H),7.66(d,1H),7.59(d,1H),7.5 0(dd,1H),7.15-7.09(m,2H),6.53(s,1H),5.23(s,2H),5.03(d,2H),3.36(s,3H).LC-MS(m / z,ESI):605.17(M+H) + .

[0299] Example 47: Preparation of compound 81.21

[0300] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.14 g (0.74 mmol) of 4-cyanobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.16 g of an oily substance, which was compound 81.21. 1 H NMR(600MHz,DMSO-d6)δ7.99(dd,1H),7.87(d,1H),7.86-7.83(m,2H),7.52-7.48(m,3H),7.14- 7.10(m,2H),6.53(s,1H),5.27(s,2H),5.04(d,2H),3.36(s,3H).LC-MS(m / z,ESI):605.17(M+H) + .

[0301] Example 48: Preparation of compound 81.34

[0302] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.18 g (0.74 mmol) of 2-bromobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of an oily substance, which was compound 81.34. 1H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.64(d,1H),7.48(dd,1H),7.43-7.38(m,2H),7.31-7.27( m,1H),7.13-7.09(m,2H),6.52(s,1H),5.19(s,2H),5.03(d,2H),3.36(s,3H).LC-MS(m / z,ESI):658.12(M+H) + .

[0303] Example 49: Preparation of compound 81.35

[0304] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.18 g (0.74 mmol) of 3-bromobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 81.35. 1 H NMR(600MHz,DMSO-d6)δ7.99(dd,1H),7.87(d,1H),7.54-7.47(m,3H),7.34-7.30(m,2H),7.14- 7.09(m,2H),6.53(s,1H),5.17(s,2H),5.01(d,2H),3.36(s,3H).LC-MS(m / z,ESI):658.18(M+H) + .

[0305] Example 50: Preparation of compound 81.36

[0306] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.18 g (0.74 mmol) of 4-bromobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 81.36. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.57-7.53(m,2H),7.50-7.47(m,1H),7.26(d,2H), 7.13-7.09(m,2H),6.53(s,1H),5.13(s,2H),4.99(d,2H),3.36(s,3H).LC-MS(m / z,ESI):658.08(M+H) + .

[0307] Example 51: Preparation of compound 81.37

[0308] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.16 g (0.74 mmol) of 2-nitrobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.21 g of a white solid, which was compound 81.37. 1H NMR(600MHz,DMSO-d6)δ8.13(dd,1H),7.99(dd,1H),7.86(d,1H),7.82-7.76(m,1H),7.66-7.60(m,2H),7.50( dd,1H),7.14-7.09(m,2H),6.50(s,1H),5.51(s,2H),5.06(d,2H),3.35(s,3H).LC-MS(m / z,ESI):625.12(M+H) + .

[0309] Example 52: Preparation of compound 81.38

[0310] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.16 g (0.74 mmol) of 3-nitrobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to give 0.17 g of a white solid, which was compound 81.38. 1 H NMR(600MHz,DMSO-d6)δ8.21-8.16(m,2H),7.95(dd,1H),7.87(d,1H),7.80-7.77(m,1H),7.69-7.67(m,1H),7.51- 7.47(m,1H),7.14-7.09(m,2H),6.53(s,1H),5.32(s,2H),5.03(d,2H),3.36(s,3H).LC-MS(m / z,ESI):625.22(M+H) + .

[0311] Example 53: Preparation of compound 81.47

[0312] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 3-methoxybenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 81.47. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.48(dd,1H),7.29-7.23(m,1H),7.13-7.08(m,2H),6.90- 6.84(m,3H),6.52(s,1H),5.12(s,2H),5.00(d,2H),3.73(s,3H),3.36(s,3H).LC-MS(m / z,ESI):610.17(M+H) + .

[0313] Example 54: Preparation of compound 81.48

[0314] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 4-methoxybenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of an oily substance, which was compound 81.48. 1H NMR(600MHz,DMSO-d6)δ7.96(dd,1H),7.86(d,1H),7.47(dd,1H),7.25-7.21(m,2H),7.13-7.08(m,2H),6.92- 6.87(m,2H),6.53(s,1H),5.07(s,2H),4.95(d,2H),3.75(s,3H),3.36(s,3H).LC-MS(m / z,ESI):610.19(M+H) + .

[0315] Example 55: Preparation of compound 81.51

[0316] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.17 g (0.74 mmol) of 4-(difluoromethoxy)benzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 81.51. 1 H NMR(600MHz,DMSO-d6)δ7.96(dd,1H),7.86(d,1H),7.48(dd,1H),7.37-7.35(m,2H),7.24(s,1H)7.18-7.14( m,2H),7.13-7.07(m,2H),6.53(s,1H),5.15(s,2H),4.98(d,2H),3.36(s,3H).LC-MS(m / z,ESI):646.22(M+H) + .

[0317] Example 56: Preparation of compound 81.55

[0318] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 2,3-difluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of an oily substance, which was compound 81.55. 1 H NMR(600MHz,DMSO-d6)δ7.92(dd,1H),7.87(d,1H),7.49-7.46(m,1H),7.46-7.42(m,1H),7.24-7.20(m,2 H),7.12-7.09(m,2H),6.53(s,1H),5.24(d,2H),4.99(d,2H),3.37(s,3H).LC-MS(m / z,ESI):616.15(M+H) + .

[0319] Example 57: Preparation of compound 81.58

[0320] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 2,6-difluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.16 g of an oily substance, which was compound 81.58. 1H NMR(600MHz,DMSO-d6)δ7.90-7.79(m,2H),7.54-7.48(m,1H),7.46-7.41(m,1H),7.20-7.03 (m,4H),6.54(s,1H),5.20(s,2H),4.93(d,2H),3.37(s,3H).LC-MS(m / z,ESI):616.19(M+H) + .

[0321] Example 58: Preparation of compound 81.59

[0322] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.15 g (0.74 mmol) of 3,4-difluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.14 g of an oily substance, which was compound 81.59. 1 H NMR (600MHz, DMSO-d6) δ7.95(dd,1H),7.86(d,1H),7.48(dd,1H),7.45-7.40(m,1H),7.38-7.34(m,1H),7.19-7. 15(m,1H),7.13-7.08(m,2H),6.53(s,1H),5.14(s,2H),5.00(d,2H),3.36(s,3H).LC-MS(m / z,ESI):616.13(M+H) + .

[0323] Example 59: Preparation of compound 81.60

[0324] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the acetic acid. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the flask, followed by 0.15 g (0.74 mmol) of 3,5-difluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.17 g of an oily substance, which was compound 81.60. 1 H NMR(600MHz,DMSO-d6)δ7.96(dd,1H),7.86(d,1H),7.50(dd,1H),7.20-7.15(m,1H),7.14-7.09(m,2H) ,7.05-7.00(m,2H),6.52(s,1H),5.19(s,2H),5.04(d,2H),3.36(s,3H).LC-MS(m / z,ESI):616.33(M+H) + .

[0325] Example 60: Preparation of compound 81.88

[0326] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the solution. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.16 g (0.74 mmol) of 4-(methylthio)benzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the solution was removed and concentrated. Purification by silica gel column chromatography yielded 0.18 g of an oily substance, which was compound 81.88. 1H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.48(dd,1H),7.24-7.23(m,4H),7.12-7.09(m,2 H),6.53(s,1H),5.11(s,2H),4.98(d,2H),3.36(s,3H),2.47(s,3H).LC-MS(m / z,ESI):626.16(M+H) + .

[0327] Example 61: Preparation of compound 81.93

[0328] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.17 g (0.74 mmol) of 3,4-dichlorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.15 g of an oily substance, which was compound 81.93. 1 H NMR(600MHz,DMSO-d6)δ7.97(dd,1H),7.86(d,1H),7.63(d,1H),7.55-7.52(m,1H),7.49(dd,1H),7.30(dd, 1H),7.14-7.09(m,2H),6.52(s,1H),5.17(s,2H),5.01(d,2H),3.36(s,3H).LC-MS(m / z,ESI):648.14(M+H) + .

[0329] Example 62: Preparation of compound 81.185

[0330] 0.30 g (0.61 mmol) of 2-((3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.17 g (1.23 mmol) of potassium carbonate was added to the reaction flask, followed by 0.16 g (0.74 mmol) of 2,4,5-trifluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.16 g of an oily substance, which was compound 81.185. 1 H NMR(600MHz,DMSO-d6)δ7.92(dd,1H),7.86(d,1H),7.62-7.57(m,1H),7.54-7.49(m,1H),7.48(dd,1H) ,7.13-7.07(m,2H),6.53(s,1H),5.16(s,2H),4.99(d,2H),3.36(s,3H).LC-MS(m / z,ESI):634.16(M+H) + .

[0331] Example 63: Preparation of compound 85.1

[0332] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.68 mmol) of 2-fluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.20 g of an oily substance, which was compound 85.1. 1H NMR(600MHz,DMSO-d6)δ7.99-7.91(m,2H),7.48-7.34(m,3H),7.26-7.16(m,2H),7.11-7.05 (m,2H),6.52(s,1H),5.20(s,2H),4.99(d,2H),3.36(s,3H).LC-MS(m / z,ESI):642.17(M+H) + .

[0333] Example 64: Preparation of compound 85.2

[0334] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.68 mmol) of 3-fluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.21 g of an oily substance, which was compound 85.2. 1 H NMR(600MHz,DMSO-d6)δ7.99-7.95(m,2H),7.47(dd,1H),7.42-7.38(m,1H),7.17-7.11(m,4H), 7.07(d,1H),6.53(s,1H),5.19(s,2H),5.02(d,2H),3.36(s,3H).LC-MS(m / z,ESI):642.18(M+H) + .

[0335] Example 65: Preparation of compound 85.3

[0336] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.68 mmol) of 4-fluorobenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.18 g of an oily substance, which was compound 85.3. 1 H NMR(600MHz,DMSO-d6)δ7.99-7.95(m,2H),7.45(dd,1H),7.37-7.34(m,2H),7.21-7.16(m,2H),7.11-7.0 8(m,1H),7.06(d,1H),6.53(s,1H),5.14(s,2H),4.98(d,2H),3.36(s,3H).LC-MS(m / z,ESI):642.16(M+H) + .

[0337] Example 66: Preparation of compound 85.4

[0338] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.68 mmol) of 2-methylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 85.4. 1H NMR(600MHz,DMSO-d6)δ7.98-7.93(m,2H),7.46-7.42(m,1H),7.27-7.22(m,2H),7.20-7.15(m,2H),7.11-7 .06(m,2H),6.52(s,1H),5.15(s,2H),4.99(d,2H),3.36(s,3H),2.22(s,3H).LC-MS(m / z,ESI):638.21(M+H) + .

[0339] Example 67: Preparation of compound 85.5

[0340] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.68 mmol) of 3-methylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.17 g of an oily substance, which was compound 85.5. 1 H NMR(600MHz,DMSO-d6)δ8.00-7.94(m,2H),7.48-7.45(m,1H),7.25-7.20(m,1H),7.13-7.03(m,5H ),6.52(s,1H),5.11(s,2H),4.99(d,2H),3.35(s,3H),2.27(s,3H).LC-MS(m / z,ESI):638.25(M+H) + .

[0341] Example 68: Preparation of compound 85.6

[0342] 0.30 g (0.56 mmol) of 2-((3-(2-bromo-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)pyridin-2-yl)oxy)acetic acid was placed in a 25 mL round-bottom flask. 5 mL of N,N-dimethylformamide was added to dissolve and dilute the mixture. After complete dissolution, 0.15 g (1.12 mmol) of potassium carbonate was added to the reaction flask, followed by 0.13 g (0.68 mmol) of 4-methylbenzyl bromide. The mixture was stirred and reacted at 50 °C for 2 hours. TLC analysis showed the reaction was complete. The mixture was extracted with water and dichloromethane, retaining the organic phase. After drying with anhydrous magnesium sulfate, the organic phase was concentrated and purified by silica gel column chromatography to obtain 0.19 g of an oily substance, which was compound 85.6. 1 H NMR(600MHz,DMSO-d6)δ7.99-7.94(m,2H),7.46(dd,1H),7.19-7.14(m,4H),7.12-7.09(m,1H),7.06(d ,1H),6.52(s,1H),5.10(s,2H),4.97(d,2H),3.36(s,3H),2.29(s,3H).LC-MS(m / z,ESI):638.22(M+H) + .

[0343] Bioactivity assay

[0344] Example 69: Indoor herbicidal activity test

[0345] The herbicidal activity test method for the compounds of this invention is as follows:

[0346] Quantities of grass weeds (barnyard grass, golden foxtail) and broadleaf weeds (zinnia, velvetleaf) seeds were sown separately in 7 cm diameter paper cups filled with nutrient soil. After sowing, the seeds were covered with 1 cm of soil, compacted, and watered. The cups were then cultivated in a greenhouse using conventional methods. Foliar spraying was applied when the grass weeds reached the 2-3 leaf stage and the broadleaf weeds reached the 2-4 leaf stage. Spraying was performed using a tracked crop sprayer (designed and manufactured by Engineer Research Ltd., UK) at the designed dosage (spraying pressure 1.95 kg / cm²). 2 Spray volume 500L / hm 2 (Track speed 1.48 km / h). The experiment was repeated three times. After treatment, the test materials were placed in the operating hall and allowed to air dry naturally before being placed in a greenhouse and managed using conventional methods. The response of weeds to the pesticide was observed and recorded. The weed control effect of the tested pesticide was visually assessed periodically after treatment. The control effect was graded as follows: 0% for ineffective, and 100% for completely killing or severely suppressing weeds.

[0347] The herbicidal activity test results of the compounds of this invention are as follows:

[0348] 2.34g ai / hm 2 Below, compounds 1.1, 1.2, 1.4, 1.23, 1.25, 1.30, 1.34, 1.45, 1.368, 1.680, 5.1, 5.2, 5.4, 5.23, 5.25, 5.30, 5.34, 5.45, 5.368, 5.680, 7.1, 7.45, 21.1, 21.56, 21.62, 21.368, 25.1, 25.56, 25.62, 25.368, 61.56, 61.62, 81.1, 81.2, 81.3, 81.4, 81.5, 81.6 The control efficacy of the following herbs against zinnia, velvetleaf, golden foxtail, and barnyard grass is no less than 80%.

[0349] Example 70: Indoor Comparison Experiment on Herbicidal Activity

[0350] Following the experimental method of Example 69, a parallel comparative experiment on the herbicidal activity of some compounds of the present invention and control compounds CK1 to CK11 was further conducted. The experimental results are shown in Tables 3, 4 and 5.

[0351] Table 3. Parallel comparative tests of the herbicidal activity of some compounds of the present invention and control compounds CK1-CK7 against *Gnaphalium affine* and *Barnyardgrass*.

[0352] Table 4. Parallel comparative tests of the herbicidal activity of some compounds of the present invention and control compounds CK8 and CK9 against *Gnaphalium affine* and *Barnyardgrass*.

[0353] Table 5. Parallel comparative tests of the herbicidal activity of some compounds of the present invention and control compounds CK10 and CK11 against zinnia and velvetleaf.

[0354] In Tables 3, 4, and 5, CK2 to CK11 are additional control compounds provided in this application. Control compounds CK1 to CK11 can be obtained by referring to the methods of the embodiments of this invention. The raw materials are all obtainable by the methods of the embodiments of this invention, are commercially available, or can be prepared by conventional methods.

[0355] CK1: White solid. 1 H NMR(600MHz,Chloroform-d)δ7.91(dd,1H),7.36(d,1H),7.33-7.29(m,1H),6.95-6.89(m,2H),6.29( s,1H),4.98-4.86(m,2H),4.18-4.14(m,2H),3.50(s,3H),1.24(t,3H).LC-MS(m / z,ESI):518.00(M+H) + .

[0356] CK2: Oily substance. 1 H NMR(600MHz,DMSO-d6)δ7.99(dd,1H),7.87(d,1H),7.50(dd,1H),7.13-7.06(m,2H),6.54(s,1H),4. 94(d,2H),4.20-4.12(m,2H),3.45(t,2H),3.37(s,3H),3.18(s,3H).LC-MS(m / z,ESI):548.18(M+H) + .

[0357] CK3: Oily substance. 1 H NMR(600MHz,DMSO-d6)δ7.99(dd,1H),7.87(d,1H),7.50(dd,1H),7.11(dd,2H),6.54(s,1H),4.94(d,2H ),4.18-4.13(m,2H),3.53-3.46(m,2H),3.42-3.34(m,6H),1.04(t,3H).LC-MS(m / z,ESI):562.21(M+H) + .

[0358] CK4: Oily substance. 1H NMR(600MHz,Chloroform-d)δ7.91(dd,1H),7.36(d,1H),7.31(dd,1H),6.92(dd,2H),6.29(s,1H),5.04-4.88(m,2H ),4.29-4.14(m,2H),3.64-3.55(m,2H),3.41-3.32(m,2H),1.56(q,2H),0.90(t,3H).LC-MS(m / z,ESI):576.21(M+H) + .

[0359] CK5: White solid. 1 H NMR(600MHz,DMSO-d6)δ7.98(dd,1H),7.87(d,1H),7.49(dd,1H),7.15-7.06(m,2H),6.55(s,1H),4.93(d,2H) ,4.15-4.11(m,2H),3.52-3.47(m,3H),3.37(s,3H),1.03(s,3H),1.02(s,3H).LC-MS(m / z,ESI):576.19(M+H) + .

[0360] CK6: Yellow solid. 1 H NMR(600MHz,DMSO-d6)δ8.02-7.92(m,2H),7.46(dd,1H),7.12-7.05(m,2H),6.53(d, 1H),4.91(d,2H),4.11(q,2H),3.37(s,3H),1.16(m,3H).ESI-MS(m / z):584.04[M+Na] + .

[0361] CK7: Yellow solid. 1 H NMR(600MHz,DMSO-d6)δ8.04(d,1H),7.97(dd,1H),7.41(dd,1H),7.08(dd,1H),6.95(d,1H), 6.52(s,1H),4.91(d,2H),4.11(q,2H),3.36(s,3H),1.16(t,3H).ESI-MS(m / z):610.09[M+H] + .

[0362] CK8: Oily substance. 1H NMR(600MHz,DMSO-d6)δ7.98(dd,1H),7.87(d,1H),7.49(dd,1H),7.20-7.05(m,2H),6.54(s,1H ),4.93(d,2H),4.21(t,2H),3.37(s,3H),2.66(t,2H),2.06(s,3H).ESI-MS(m / z):586.08[M+Na] + .

[0363] CK9: White solid. 1 H NMR(600MHz,Chloroform-d)δ7.87(dd,1H),7.33(d,1H),7.27(dd,1H),6.96-6.78(m,2H),6.26(s,1H ),4.98-4.80(m,2H),3.47(s,3H),2.68(t,2H),2.51(q,2H),1.21(s,3H).ESI-MS(m / z):600.16[M+Na] + .

[0364] CK10: White solid. 1 H NMR(600MHz,DMSO-d6)δ7.97(d,1H),7.86(d,1H),7.48(d,1H),7.36-7.28(m,5H),7.10 (d,2H),6.53(s,1H),5.15(s,2H),5.00(d,2H),3.36(s,3H).ESI-MS(m / z):580.26[M+H] + .

[0365] CK11: Oily substance. 1 H NMR(600MHz,DMSO-d6)δ7.98-7.96(m,2H),7.46(dd,1H),7.37-7.29(m,5H),7.12-7.09(m,1H) ,7.06(d,1H),6.52(s,1H),5.15(s,2H),4.99(d,2H),3.36(s,3H).ESI-MS(m / z):624.16[M+H] + .

[0366] By comparing the compounds of the present invention with control compounds CK1-CK11, it can be seen that the compounds of the present invention have unexpectedly high herbicidal activity and substantial progress compared with the prior art.

Claims

1. A uracil compound, characterized in that, The compound is shown in general formula I: In general formula I: R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, amino, C1-C6 alkyl or halo-C1-C6 alkyl; X is selected from O or S; Q is selected from one of the groups shown in Q1-Q3: Q1: -CH2OR3; Q2:-CH2S(=O) m R4; Q3： R3 and R4 are each independently selected from C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkyl carbonyloxy C1-C6 alkyl, C1-C6 alkoxy carbonyl C1-C6 alkyl carbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6, phenyl, benzyl or phenyl carbonyl, and when the number of substituents is greater than 1, R6 may be the same or different; m is selected from 0, 1, or 2; n is selected from 1, 2, 3, 4, or 5; R5 and R6 are each independently selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkylthio or halo-C1-C6 alkylthio. It may be a stereoisomer of a compound of general formula I; It may be a salt of a compound of general formula I; It may be a salt of a stereoisomer of a compound of general formula I.

2. The compound according to claim 1, characterized in that, In general formula I: R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, amino, C1-C4 alkyl or halo-C1-C4 alkyl; X is selected from O or S; Q is selected from one of the groups shown in Q1-Q3: Q1: -CH2OR3; Q2:-CH2S(=O) m R4; Q3： R3 and R4 are each independently selected from C1-C4 alkyl, halo-C1-C4 alkyl, C1-C4 alkyl carbonyl, C1-C4 alkoxy carbonyl, C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkyl carbonyloxy C1-C4 alkyl, C1-C4 alkoxy carbonyl C1-C4 alkyl carbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6, phenyl, benzyl or phenyl carbonyl, and when the number of substituents is greater than 1, R6 may be the same or different; m is selected from 0, 1, or 2; n is selected from 1, 2, 3, 4, or 5; R5 and R6 are each independently selected from halogen, cyano, nitro, C1-C4 alkyl, halo-C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C1-C4 alkylthio or halo-C1-C4 alkylthio. It may be a stereoisomer of a compound of general formula I; Salts formed by compounds of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid. Salts formed by the stereoisomer of a compound of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

3. The compound according to claim 2, characterized in that, In general formula I: R1 and R2 are each independently selected from hydrogen, halogen, cyano, nitro, amino, C1-C4 alkyl or halo-C1-C4 alkyl; X is selected from O or S; Q is selected from one of the groups shown in Q1-Q3: Q1: -CH2OR3; Q2:-CH2S(=O) m R4; Q3： R3 and R4 are each independently selected from C1-C4 alkyl, halo-C1-C4 alkyl, C1-C4 alkyl carbonyl, C1-C4 alkoxy carbonyl, C1-C4 alkoxy C1-C2 alkyl, C1-C4 alkyl carbonyloxy C1-C2 alkyl, C1-C4 alkoxy carbonyl C1-C2 alkyl carbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6, phenyl, benzyl or phenyl carbonyl, and when the number of substituents is greater than 1, R6 may be the same or different; m is selected from 0, 1, or 2; n is selected from 1, 2, 3, 4, or 5; R5 and R6 are each independently selected from halogen, cyano, nitro, C1-C4 alkyl, halo-C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C1-C4 alkylthio or halo-C1-C4 alkylthio. It may be a stereoisomer of a compound of general formula I; Salts formed by compounds of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid. Salts formed by the stereoisomer of a compound of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

4. The compound according to claim 1, characterized in that, In general formula I: R1 and R2 are each independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, or perfluoroethyl. X is selected from O or S; Q is selected from one of the groups shown in Q1-Q3: Q1: -CH2OR3; Q2:-CH2S(=O) m R4; Q3： R3 and R4 are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, perfluoroethyl, 1,1,1,3,3,3-hexafluoropropane-2-yl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, CH3OCH2-, CH3CH2OC H2-, CH3CH2CH2OCH2-, (CH3)2CHOCH2-, CH3CH2CH2CH2OCH2-, (CH3)3COCH2-, CH3OCH2CH2-, CH3CH2OCH2CH2-, CH3CH2CH2OCH2CH2-, CH3CH2CH2CH2OCH2CH2-, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, methylcarbonyloxyethyl, ethylcarbonyloxyethyl, methoxycarbonylmethylcarbonyl, ethoxycarbonylmethylcarbonyl, tert-butoxycarbonylethylcarbonyl, unsubstituted or substituted with 1, 2, 3, 4 or 5 R6 groups, and when the number of substituents is greater than 1, the R6 groups may be the same or different; m is selected from 0, 1, or 2; n is selected from 1, 2, 3, 4, or 5; R5 and R6 are each independently selected from fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, monochloromethyl, dichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, heptafluoroisopropyl, perfluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, monofluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, or 2,2,2-trifluoroethylthio. It may be a stereoisomer of a compound of general formula I; Salts formed by compounds of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid. Salts formed by the stereoisomer of a compound of general formula I with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, trifluoroacetic acid, oxalic acid, malonic acid, methanesulfonic acid, 4-toluenesulfonic acid, malic acid, fumaric acid, lactic acid, maleic acid, salicylic acid, tartaric acid, or citric acid.

5. The application of a compound of general formula I or a salt thereof, or a stereoisomer of a compound of general formula I or a salt thereof, for the control of weeds.

6. A herbicidal composition, characterized in that: The active component is a compound of general formula I as described in claim 1 or a salt thereof, or a stereoisomer of general formula I or a salt thereof, and the weight percentage of the active component in the composition is 0.1-99%.

7. The application of the herbicidal composition according to claim 6 for the control of weeds.

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