An N-phenylpyrimidinedione derivative, and a preparation method and application thereof

Abstract

The present application relates to the technical field of compound synthesis and pesticides, and particularly relates to a kind of N Phenylpyrimidine diketone derivatives, preparation method and application thereof N The phenylpyrimidine diketone derivatives have 100% prevention and removal effect on gramineous weeds and broadleaf weeds at a dose of 9.375-150 a.i.g / ha; the compounds can obtain good herbicidal effect at a low dose, and can be used as potential PPO inhibitors and post-emergence herbicides, the derivative has novel structure, simple preparation process, low production cost and wide application prospect.

Description

Technical Field

[0001] This invention belongs to the field of compound pesticides, specifically relating to a... N -Phenylenidine dione derivatives, their preparation methods and applications. Background Technology

[0002] Herbicides play a vital role in modern agriculture, effectively controlling weeds and ensuring crop yields. Over the past few decades, the development and application of herbicides have undergone profound changes to address ongoing challenges such as weed resistance, environmental safety, and the need for sustainable agriculture. Therefore, developing efficient and environmentally friendly herbicides has become a major requirement in current agricultural production.

[0003] Protoporphyrinogen oxidase (PPO) catalyzes the oxidation of protoporphyrinogen IX to protoporphyrin IX, and is one of the most important targets discovered in herbicide research. Protoporphyrinogen oxidase is the penultimate enzyme in the biosynthesis of chlorophyll and heme, belonging to a large family of enzymes containing flavonoid adenine dinucleotides (FAD). It catalyzes the conversion of protoporphyrinogen IX to protoporphyrin IX. Inhibition of PPO by plants can lead to the toxic accumulation of protoporphyrin IX in the cytoplasm. Under light, protoporphyrin IX reacts with oxygen to produce reactive oxygen species, damaging cell membranes and causing rapid burn symptoms in plants. On the other hand, PPO inhibitors have many advantages, including broad-spectrum herbicidal activity, strong resistance to herbicides, environmental friendliness, low toxicity, and low usage rates. N β-Phenyrimidine diones play a crucial role among PPO inhibitors, currently based on N Several commercial drugs have been developed for phenylpyrimidine dione, such as pyrimisulfuron, flupropargyl, bispyribac-methyl, and flupyrimisulfuron. Therefore, based on... N The design and synthesis of small molecules of herbicides using phenylpyrimidine dione is in line with the current trend in the creation of new pesticides.

[0004] Application No. 202411631927.5 discloses a "sulfonyl uridine compound and its application". These compounds have good control effects on broadleaf weeds, but their effectiveness against grass weeds still needs to be further improved.

[0005] The patent with publication number CN107382896B discloses the application of benzoxazole-2-oxyphenoxypropionimide compounds in weed control, but it mainly addresses the control of weeds in rice paddies and targets grass weeds. Its effectiveness in controlling broadleaf weeds is unknown. Furthermore, the structure is large and complex, which is not conducive to the formation of low-molecular-weight compounds.

[0006] Patent application CN1407854A discloses a class of herbicides based on the N-aryluracil structure. The key difference between this application and the previous one lies in the significant difference in the substituent group at the 3-position branch of the pyrimidine dione core. This application, through structural modification and optimization at this position, yields compounds with significantly enhanced herbicidal activity against both grassy and broadleaf weeds, exhibiting higher weed control efficacy. Therefore, the compounds described in this application have significant application potential in the development of novel herbicides. Summary of the Invention

[0007] To overcome the aforementioned problems in the prior art, the present invention provides a N phenylpyrimidine dione derivatives and their applications, including N Herbicidal compositions of phenylpyrimidine dione derivatives and their applications, herbicides, the aforementioned N 1-Phenyrimidine dione derivatives exhibit high herbicidal activity when used to control weeds and have significant application potential.

[0008] To achieve the above objectives, the technical solution adopted by the present invention is as follows: One of the objectives of this invention is to provide: a N -Phenyrimidine dione derivatives, the N The general structural formula of phenylpyrimidine dione derivatives is shown in formula (I): 1. A kind N -Phenylenidine dione derivative, characterized in that, N The general structural formula of phenylpyrimidine dione derivatives is shown in formula (I): In formula (I): X 1 X 2 Selected from O and S respectively; R 1 : C1-C6 alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy; R 2 C1-C6 alkyl, C1-C6 haloalkyl; R 3 Hydrogen or C1-C6 alkyl; R 4 H, nitro, amino, cyano, halogen; R 5 H, nitro, amino, cyano, halogen; R 6 H, halogen, C1-C3 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl; R 7 Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 halocycloalkylcarbonyl, C3-C6 cycloalkenylcarbonyl, C3-C6 halocycloalkenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, C1-C6 alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminothiocarbonyl, C1-C6 alkylthioC2-C6 alkylcarbonyl, and unselected. The phenyl C1-C2 alkyl, phenyl carbonyl, phenyl C1-C2 alkyl carbonyl, phenyl C2-C4 alkenyl carbonyl, phenoxy C1-C2 alkyl carbonyl, thiophene carbonyl, pyrazole carbonyl, quinoline carbonyl: halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl or substituted with 1-4 halogens, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, CR 8 R 9 ; R 8 R 9 : Selected from hydrogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkylCOOR, respectively, or in different forms. 10 COOR 10 CH2OR 11 CH2NR 12 R 13 CONR 12 R 13 A phenyl group that is unsubstituted or substituted by 1-4 independently selected from the following groups; a pyridyl group that is unsubstituted or substituted by 1-4 independently selected from the following groups; a halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl, COOR 10 CONR 12 R 13 ; R 10: Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylcarbonyloxy-C2-C4 alkyl, unsubstituted or substituted by 1-4 independently selected from the following groups: benzyl, furanylene, thiazolemethylene, tetrahydrofuranylene or pyridinylene, where the following groups are halogens, CN, NO2, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl; R 11 Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 halocycloalkylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, C1-C6 alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminothiocarbonyl, C1-C6 alkylthioC2-C6 alkylcarbonyl, unsubstituted or substituted by 1-4 independently selected from the following groups, phenyl, phenylC1 -C2 alkyl, phenyl C2-C4 alkenyl, phenyl carbonyl, phenyl C1-C2 alkyl carbonyl, phenoxy C1-C2 alkyl carbonyl, phenyl C2-C4 alkenyl carbonyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryl carbonyl, the following groups being halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy carbonyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl or phenoxy groups independently substituted by 1-4 halogens, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R 12 R 13 : Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxycarbonylC1-C6 alkyl, SO2NH(C1-C6 alkyl) or SO2N(C1-C6 alkyl)(C1-C6 alkyl); X: C, O, S, NH, COO, CHNO, SO2NH, NHSO2 or unsubstituted; Z: CH2, CH(CH3), C(CH3)2; n is selected from 0, 1, 2, 3, 4, 5, and 6 respectively; The N The preparation method of phenylpyrimidine dione derivatives includes the following steps: Compound L1: (E)-3-(1-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)methyl benzoate; Compound L2: (E)-4-(1-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)methyl benzoate; Compound L3: (E)-2-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methyl benzoate; Compound L4: (E)-3-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)methyl)ethyl benzoate; Compound L5: (E)-4-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methyl benzoate; Compound L6: (E)-3-(4-chloro-2-fluoro-5-((((1-(2-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L7: (E)-3-(4-chloro-2-fluoro-5-(((1-(3-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L8: (E)-3-(4-chloro-2-fluoro-5-((((1-(4-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L9: (E)-2-methoxybenzaldehyde o-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl) oxime; Compound L10: (E)-3-methoxybenzaldehyde o-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl) oxime; Compound L11: (E)-4-methoxybenzaldehyde o-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl) oxime; Compound L12: (E)-3-(4-chloro-2-fluoro-5-((((1-(2-fluorophenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L13: (E)-3-(4-chloro-2-fluoro-5-(((1-(2-fluoro-4-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L14: 3-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclobutane-1-carboxylic acid methyl ester; Compound L15: (Z)-2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L16: (E)-3-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L17: (E)-3-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L18: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L19: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid propyl ester; Compound L20: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid isopropyl ester; Compound L21: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)-1-methylcyclohexane-1-carboxylic acid methyl ester; Compound L22: 2-(4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L23: (E)-2-(2-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L24: (E)-4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)-imino)-2-methylcyclohex-2-ene-1-carboxylic acid ethyl ester; Compound L25: S-ethyl 4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L26: S-isopropyl4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L27: S-propyl 4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L28: (E)-6-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl) nicotinic acid methyl ester; Compound L29: (E)-6-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methylpyridinecarboxylate; Compound L30: (E)-5-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methylpyridinecarboxylate; Compound L31: (E)-2-(1-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)methyl isonicotinic acid; Compound L32: (E)-5-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)furan-2-carboxylic acid methyl ester; Compound L33: (E)-5-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)thiophene-2-carboxylic acid methyl ester; Compound L34: (E)-5-(1-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)thiophene-2-carboxylic acid methyl ester; Compound L35: (E)-3-(4-chloro-2-fluoro-5-((1-(((1-(3-methoxyphenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L36: (E)-3-(4-chloro-2-fluoro-5-((1-(((1-(4-methoxyphenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L37: (E)-2-methoxybenzaldehyde O-(2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxime; Compound L38: (E)-3-methoxybenzaldehyde O-(2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxime; Compound L39: (E)-4-methoxybenzaldehyde O-(2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxime; Compound L40: (E)-3-(1-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)ethyl)methyl benzoate; Compound L41: (E)-4-(1-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)ethyl)methyl benzoate; Compound L42: (E)-2-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)benzoate; Compound L43: (E)-3-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)benzoate; Compound L44: (E)-4-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)benzoate; Compound L45: (E)-3-(4-chloro-2-fluoro-5-((1-((1-(2-fluoro-4-methoxyphenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L46: (E)-3-(4-chloro-2-fluoro-5-((1-(((1-(2-fluorophenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L47: 3-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclobutane-1-carboxylic acid methyl ester; Compound L48: (E)-2-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L49: (E)-3-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L50: (E)-3-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L51: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid methyl ester; Compound L52: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L53: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid propyl ester; Compound L54: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid isopropyl ester; Compound L55: S-ethyl 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L56: S-propyl-4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyloxy)imino)cyclohexane-1-thiocarboxylic acid ester; Compound L57: S-isopropyl4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L58: 4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)-imino)-1-methylcyclohexane-1-carboxylic acid methyl ester; Compound L59: (E)-2-(2-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L60: 2-(4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L61: (E)-4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)-2-methylcyclohex-2-ene-1-carboxylic acid ethyl ester; Compound L62: (E)-4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)-2,6-dimethylcyclohex-2-ene-1-carboxylic acid methyl ester; Compound L63: (E)-5-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)thiophene-2-carboxylic acid methyl ester.

[0009] The N The preparation method of phenylpyrimidine dione derivatives includes the following steps: (1) Preparation of intermediate 3: NaH was dissolved in DMF, and intermediate 1 was slowly added under ice bath conditions. After stirring in an ice bath for 10 minutes, the mixture was brought to room temperature and stirred for 1 hour. Then, intermediate 2 was slowly added dropwise under ice bath conditions, followed by a reaction at room temperature for 2 hours. The resulting intermediate 3 was extracted with water and ethyl acetate, respectively, and obtained by column chromatography. Intermediate 1 was... The intermediate 2 is ; (2) Preparation of intermediate 5: Intermediate 4, ammonium chloride, and 90% ethanol solution were mixed and stirred, then heated to 80°C. Iron powder was then slowly added, and the reaction system was allowed to react at 80°C for 4 hours. The remaining iron powder was removed by filtration, and then the mixture was subjected to extraction, drying, and column chromatography to obtain intermediate 5. Intermediate 4 is... ; (3) Preparation of intermediate 6: Intermediates 3 and 5 were dissolved in acetic acid and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with water and ethyl acetate. The organic layer was dried by rotary evaporation to obtain intermediate 6, which did not require further purification and was directly added to the next step. (4) Preparation of intermediate 7: Intermediate 6 was dissolved in DMF, and then K2CO3 and R were added respectively. 1 I. Stir at room temperature for 4 hours. After the reaction is complete, extract repeatedly with water and ethyl acetate, then dry with anhydrous sodium sulfate, and finally obtain intermediate 7 by column chromatography. (5) Preparation of intermediate 8: Intermediate 7 was dissolved in a mixed acid, and CrO3 was added in batches under ice bath conditions. The mixture was stirred for 8 hours, quenched with water, extracted with ethyl acetate, dried the organic layer, evaporated under vacuum, and finally obtained intermediate 8 by column chromatography. The mixed acid was composed of acetic acid and sulfuric acid in a volume ratio of AcOH:H2SO4 = 4:1. (6) Preparation of target compounds L1–L34: Intermediate 8, DCC, DMAP and R 7 NOH was added to CH2Cl2 and stirred at room temperature for 6 hours. After the reaction was completed by TLC monitoring, water was added to quench the reaction, and then extraction was performed. The target compounds L1–L34 were obtained by column chromatography. (7) Preparation of intermediate 11: Intermediates 9 and 10 were dissolved in potassium carbonate in DMF and stirred at room temperature for 4 hours. After the reaction was complete, they were extracted, dried, and subjected to column chromatography to obtain intermediate 11. Intermediate 9 was... The intermediate 10 is ; (8) Preparation of intermediate 12: After mixing and stirring intermediate 11, ammonium chloride and 90% ethanol solution, the temperature was raised to 80°C, and then iron powder was slowly added. After the reaction system was reacted at 80°C for 4 hours, the remaining iron powder was removed by filtration, and then intermediate 12 was obtained by extraction, drying and column chromatography. (9) Preparation of intermediate 13: Intermediates 3 and 12 were dissolved in acetic acid and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with water and ethyl acetate. The organic layer was dried by rotary evaporation to obtain intermediate 13, which did not require further purification and was directly introduced to the next step. (10) Preparation of intermediate 14: Intermediate 13 was dissolved in DMF, and then K2CO3 and R were added respectively. 1 I. Stir at room temperature for 4 hours. After the reaction is complete, extract repeatedly with a large amount of water and ethyl acetate, then dry with anhydrous sodium sulfate, and finally obtain intermediate 14 by column chromatography. (11) Preparation of intermediate 15: Intermediate 15 was dissolved in a mixed acid (volume ratio: AcOH:H2SO4:H2O = 2:1:1), heated to 100℃ and refluxed for 4 hours, then poured into ice and filtered to obtain the solid. Intermediate 15 could be obtained without further purification. The mixed acid was composed of acetic acid, sulfuric acid and water in a volume ratio of AcOH:H2SO4:H2O = 2:1:1. (12) Preparation of target compounds L35–L63: Intermediate 15, DCC, DMAP and R 7 NOH was added to CH2Cl2, and the mixture was stirred at room temperature for 6 hours. After the reaction was complete as monitored by TLC, water was added to quench the reaction, followed by extraction. The target compounds L35–L63 were obtained by column chromatography.

[0010] In step (1), the amounts of intermediate 1, NaH, and intermediate 2 are calculated in molar ratio as follows: intermediate 1: NaH: intermediate 2 = 1: 2.5: 2.5; the amount of DMF is controlled by adding 1 mL of DMF to every millimole of intermediate 1.

[0011] In step (2), the amounts of intermediate 4, ammonium chloride, and iron powder are calculated in the following molar ratio: intermediate 1: ammonium chloride: iron powder = 1:3:3; the amount of 90% ethanol is controlled by adding 1 mL of 90% ethanol to every millimole of intermediate 1.

[0012] In step (3), the amounts of intermediates 3 and 5 are in a molar ratio of 3:5 = 1.5:1; the amount of acetic acid is controlled by adding 1 mL of acetic acid per millimol of intermediate 5.

[0013] In step (4), the intermediate 6, K2CO3 and R 1 The dosage of I, measured in molar ratios, is: Intermediate 6:K2CO3:R 1 I=1:1.25:1.25; The amount of DMF used is controlled according to 1 mL of DMF per millimole of intermediate 6.

[0014] In step (5), the mixed acid (volume ratio: AcOH:H2SO4 = 4:1) is controlled by adding 1 mL of mixed acid per millimol of intermediate 8.

[0015] In step (6), the intermediate 8, DCC, DMAP and R 7 The dosage of NOH, measured in molar ratios, is: Intermediate 8: DCC: DMAP: R 7 NOH = 1:1.2:0.2:1.2:; The amount of CH2Cl2 is controlled by adding 1 mL of CH2Cl2 per millimole of intermediate 8.

[0016] In step (7), the amounts of intermediate 9, intermediate 10 and potassium carbonate are in the following molar ratio: intermediate 9: intermediate 10: potassium carbonate = 1:1.25:1.25; the amount of DMF is controlled by adding 1 mL of DMF per millimol of intermediate 9.

[0017] In step (8), the amounts of intermediate 11, ammonium chloride, and iron powder are calculated in the following molar ratio: intermediate 11: ammonium chloride: iron powder = 1:3:3; the amount of 90% ethanol is controlled by adding 1 mL of 90% ethanol per millimol of intermediate 11.

[0018] In step (9), the amounts of intermediates 3 and 12 are in a molar ratio of 1.5:1 for intermediate 3 to intermediate 12; the amount of acetic acid is controlled by adding 1 mL of acetic acid per millimol of intermediate 5.

[0019] In step (10), the intermediate 13, K2CO3 and R 1 The dosage of I, measured in molar ratios, is: Intermediate 6:K2CO3:R 1 I=1:1.25:1.25; the amount of DMF used is controlled according to 1 mL of DMF per millimole of intermediate 14.

[0020] In step (11), the mixed acid (volume ratio: AcOH:H2SO4:H2O = 2:1:1) is controlled by adding 1 mL of mixed acid per millimole of intermediate 14.

[0021] In step (12), the intermediate 15, DCC, DMAP and R 7 The dosage of NOH, measured in molar ratios, is: Intermediate 15: DCC: DMAP: R 7 NOH = 1:1.2:0.2:1.2:; The amount of CH2Cl2 is controlled by adding 1 mL of CH2Cl2 per millimole of intermediate 8.

[0022] The N The preparation routes for -phenylpyrimidine dione derivatives are any of the following: Route 1: Route 2: Another object of the present invention is that... N Application of phenylpyrimidine dione derivatives in the preparation of herbicides and weed growth enzyme inhibitors.

[0023] Specifically, the weeds include barnyard grass, velvetleaf, amaranth, lambsquarters, ryegrass, purslane, bermudagrass, rapeseed, speedwell, amaranth, black nightshade, bitter lettuce, dandelion, sage, clover, chickweed, goosegrass, foxtail, etc.

[0024] Beneficial effects: This invention is based on N The phenylpyrimidine dione structure was optimized and derived to create a drug with stable physicochemical properties and excellent drug-likeness. N -Phenyrimidine dione herbicides are small molecules; these derivatives are particularly effective in post-emergence inhibition of barnyard grass, goosegrass, foxtail grass, velvetleaf, amaranth, and purslane.

[0025] Post-emergence herbicidal activity tests revealed that the vast majority of herbicides... N At doses of 150–37.5 ga.i. / ha, compounds L1–L3, L6, L14–L16, L18–L20, L26, L28, L29, and L34–L63 exhibited excellent herbicidal activity against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane, causing complete wilting of the tested weeds with inhibition rates reaching 100%, comparable to the positive control pyrimisulfuron, indicating that these compounds have great application potential.

[0026] The N-phenylpyrimidine dione derivative designed and synthesized in this invention has a simple structure and a simple preparation process. It has good herbicidal activity against both grasses and broadleaf weeds. The raw materials are readily available, the production cost is low, the overall yield is high, and the preparation process is non-toxic and harmless, showing great application prospects. Attached Figure Description

[0027] Figure 1 for N Preparation route diagram of phenylpyrimidine dione derivatives L1-L34; Figure 2 for N Preparation route diagram of -phenylpyrimidine dione derivatives L35-L63. Detailed Implementation

[0028] The specific embodiments of the present invention will be described in further detail below, but the present invention is not limited to these embodiments. Any improvements or substitutions based on the basic spirit of these embodiments shall still fall within the scope of protection claimed by the claims of the present invention.

[0029] Example 1: Preparation of compound L28 (1) Preparation of intermediate 3.

[0030] NaH (546 mmol) was added to the reaction flask, dissolved in 400 mL of DMF, and after 10 minutes on ice, intermediate 1 (218 mmol) was slowly added. After stirring for 1 hour, intermediate 2 (546 mmol) was slowly added on ice. Once the addition was complete, the ice bath was removed, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated NaCl solution, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was then subjected to column chromatography to obtain intermediate 3.

[0031] (2) Preparation of intermediate 5.

[0032] 1-Chloro-5-fluoro-2-methyl-4-nitrobenzene (1,211.0 mmol), 500 mL of 90% ethanol, and ammonium chloride (633.0 mmol) were added to a reaction flask. After stirring and heating to reflux, Fe powder was slowly added in batches. After monitoring the reaction progress by TLC, the Fe powder (633.0 mmol) was removed by diatomaceous earth filtration. The organic layer of the filtrate was extracted with ethyl acetate and water, and washed successively with water and saturated NaCl solution. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 4-chloro-2-fluoro-5-methylaniline 5.

[0033] (3) Preparation of intermediate 7.

[0034] 5 mmol of 4-chloro-2-fluoro-5-methylaniline, 225 mmol of intermediate 3, and acetic acid were added to a reaction flask and the mixture was refluxed for 4 hours. After cooling to room temperature, the mixture was extracted with water and ethyl acetate. The organic layer was washed with water and saturated NaHCO3 solution, and the solvent was removed under reduced pressure. The residue was used directly in the next step. 225 mmol of iodomethane, 225 mmol of potassium carbonate, and DMF were added to the residue, and the mixture was stirred at room temperature for 4 hours. After cooling to room temperature, the mixture was extracted with water and ethyl acetate. The organic layer was washed with water and saturated NaCl solution, and the solvent was removed under reduced pressure. The residue was then subjected to silica gel column chromatography to give 7 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione.

[0035] (4) Preparation of intermediate 8.

[0036] 3-(4-chloro-2-fluoro-5-methylphenyl)-1-methyl-6-(trifluoromethyl)pyrimidin-2,4(1H,3H)-dione 7 (148 mmol), 400 mL of acetic acid, and 100 mL of sulfuric acid were added to a reaction flask. Chromium trioxide (520 mmol) was slowly added in portions under ice bath conditions. After the addition was complete, the mixture was allowed to react at room temperature for 8 hours. The mixture was then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and saturated NaCl solution, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoic acid 8.

[0037] (5) Synthesis of target compound L28.

[0038] 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoic acid, ( E 1 mmol of methyl 6-((hydroxyimino)methyl)nicotinic acid, 1.2 mmol of dicyclohexylcarbodiimide, 0.2 mmol of 4-dimethylaminopyridine, and 15 mL of CH2Cl2 were added to a reaction flask. The mixture was stirred at room temperature for 6 hours. After the reaction was complete as monitored by TLC, the organic layer was extracted with water and washed with water and saturated NaCl solution. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give ethyl acetate A43, 2-chloro-2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino).

[0039] Other compounds L1-L34 were synthesized using the method described in Example 1, with the only difference being that the corresponding starting material was replaced with the corresponding oxime in the final step.

[0040] Example 2: Preparation of compound L45 (1) Preparation of intermediate 11: Dissolve 2-chloro-4-fluoro-5-nitrophenol 9 (30.00 g, 156.65 mmol) in 300 mL of LDM, then add potassium carbonate (32.47 g, 234.93 mmol), and slowly add methyl 2-bromopropionate 10 (16.06 g, 163.72 mmol) dropwise at room temperature. After the addition is complete, react at room temperature for 6 hours. After the reaction is complete, extract the reaction system with water and ethyl acetate, and dry to obtain solid methyl 2-(2-chloro-4-fluoro-5-nitrophenoxy)propionate intermediate 11.

[0041] (2) Preparation of intermediate 12: Methyl 2-(2-chloro-4-fluoro-5-nitrophenoxy)propionate 11 (37.60 g, 135.43 mmol), NH4Cl (21.73 g, 406.29 mmol), and EtOH (90%, 300 mL) were added to a flask, and the mixture was heated to 80 °C. Iron powder (22.69 g, 406.29 mmol) was then added in portions to the solution, and the reaction mixture was refluxed for 4 hours. After the reaction was complete, the hot reaction mixture was filtered through a diatomaceous earth mat. The residue was washed with ethyl acetate (100 mL), and H2O (200 mL) was added to the filtrate. The mixture was extracted with 200 mL of ethyl acetate, and the organic layers were combined. The extract was concentrated by rotary evaporation over anhydrous Na2SO4 to obtain methyl 2-(5-amino-2-chloro-4-fluorophenoxy)propionate intermediate 12.

[0042] (3) Preparation of intermediate 14: Methyl 2-(5-amino-2-chloro-4-fluorophenoxy)propionate intermediate 12 (188 mmol), intermediate 3 (225 mmol), and acetic acid were added to a reaction flask and refluxed for 4 hours. After cooling to room temperature, the mixture was extracted with water and ethyl acetate. The organic layer was washed with water and saturated NaHCO3 solution, and the solvent was removed under reduced pressure to obtain intermediate 13, which could be used directly in the next step without purification. Iodomethane (225 mmol), potassium carbonate (225 mmol), and DMF were added to the residue, and the mixture was stirred at room temperature for 4 hours. After cooling to room temperature, the mixture was extracted with water and ethyl acetate. The organic layer was washed with water and saturated NaCl solution, and the solvent was removed under reduced pressure. The residue was then subjected to silica gel column chromatography to obtain methyl 2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionate intermediate 14.

[0043] (4) Preparation of intermediate 15: Intermediate 14 (137.91 mmol) was added to 120 mL of HOAc, and then H2O (60 mL) and H2SO4 (60 mL) were added to the solution with stirring. The reaction solution was heated to 100 °C for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature and poured into 500 g of ice and stirred vigorously for 10 minutes. The solid was obtained by filtration, washed with H2O (50 mL), and dried under vacuum to give intermediate 15 of 2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionic acid.

[0044] (5) Synthesis of target compound L45.

[0045] Intermediate 15 (1 mmol), 1-(2-fluoro-4-methoxyphenyl)ethyl-1-one oxime (1.2 mmol), dicyclohexylcarbodiimide (1.2 mmol), 4-dimethylaminopyridine (0.2 mmol), and 15 mL of CH2Cl2 were added to a reaction flask. The mixture was stirred at room temperature for 6 hours. After the reaction was complete as monitored by TLC, the organic layer was extracted with water, washed with water and saturated NaCl solution, and the solvent was removed under reduced pressure. The residue was then subjected to silica gel column chromatography to obtain ethyl acetate L45, 2-chloro-2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino).

[0046] Other compounds L35-L63 were synthesized using the method described in Example 2, only requiring the replacement of the corresponding starting material with the corresponding oxime in the final step, for example: Preparation of compound L46: 1-(2-fluoro-4-methoxyphenyl)ethyl-1-one oxime was replaced with 1-(2-fluoro)ethyl-1-one oxime; the reaction formula is as follows: Preparation of compound L49: 1-(2-fluoro-4-methoxyphenyl)ethyl-1-one oxime was replaced with methyl 3-(hydroxyimino)cyclopentane-1-carboxylic acid; the reaction formula is as follows: Preparation of compound L51: 1-(2-fluoro-4-methoxyphenyl)ethyl-1-one oxime was replaced with methyl 4-(hydroxyimino)cyclohexane-1-carboxylic acid; the reaction formula is as follows: Preparation of compound L52: 1-(2-fluoro-4-methoxyphenyl)ethyl-1-one oxime was replaced with ethyl 4-(hydroxyimino)cyclohexane-1-carboxylate; the reaction formula is as follows: Preparation of compound L58: 1-(2-fluoro-4-methoxyphenyl)ethyl-1-one oxime was replaced with methyl 4-(hydroxyimino)-1-methylcyclohexane-1-carboxylic acid; the reaction formula is as follows: The structural and molecular formulas of the target compounds obtained in the above examples are shown in Table 1, and their physicochemical properties and spectral information are also shown in Table 1. Table 1. Molecular formulas and structural formulas of target compounds L1-L63

[0047] Table 2. Spectral data of target compounds L1-L63

[0048] Post-emergence activity test of target compounds: This experiment used a spray method with various weeds as test targets. Weed seeds were directly sown and evenly scattered in 8 x 8 cm plastic pots filled with two-thirds organic substrate soil, and then grown in a greenhouse. The compounds were tested when both grass and broadleaf weeds reached the two- to three-leaf stage. The compounds were measured using 100... μ Dissolve in LDMF and dilute with 0.1% Tween-80 to a dose of 37.5–150 g ai / ha. Trifluralin was used as a positive control and target compound to spray all weeds. After treatment, the weeds were placed in a greenhouse for 15 days, and their herbicidal activity was evaluated visually in the control group (CK), repeated three times.

[0049] Table 3. Post-emergence herbicidal activity of target compounds L1-L63

[0050] As shown in Table 3, compounds L1–L3, L6, L14–L16, L18–L20, L26, L28, L29, and L34–L63 exhibited excellent herbicidal activity against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane at doses of 150–37.5 g ai / ha. The weeds completely withered, and the inhibition rate reached 100%, comparable to the positive control benzosulfuron. Most notably, compounds L45, L46, L49, L51, L52, and L58, at a dose of 9.375 g ai / ha, all achieved 100% inhibition rates against barnyard grass, goosegrass, foxtail, velvetleaf, amaranth, and purslane, which was superior to benzosulfuron (barnyard grass: 60%, goosegrass: 80%, foxtail: 70%). The above analysis further demonstrates that these compounds are highly effective in controlling weeds and have great application potential. In summary, this series N 2-Phenyrimidine dione derivatives possess novel structures, readily available raw materials, and simple preparation processes. Most of these compounds exhibit excellent post-emergence herbicidal activity. Therefore, this series of compounds has significant potential for further development as PPO inhibitors and post-emergence herbicides, enabling their application in the field.

[0051] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any way. Any simple modifications, equivalent changes, and alterations made to the above embodiments based on the technical essence of the present invention without departing from the scope of the present invention shall still fall within the scope of the present invention.

Claims

1. A kind N -Phenyline pyrimidine dione derivative, characterized in that... The N The general structural formula of phenylpyrimidine dione derivatives is shown in formula (I): In formula (I): X 1 X 2 Selected from O and S respectively; R 1 : C1-C6 alkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C1-C6 haloalkyl, C1-C6 alkoxy; R 2 C1-C6 alkyl, C1-C6 haloalkyl; R 3 Hydrogen or C1-C6 alkyl; R 4 H, nitro, amino, cyano, halogen; R 5 H, nitro, amino, cyano, halogen; R 6 H, halogen, C1-C3 alkyl, C1-C3 alkoxy, C3-C6 cycloalkyl; R 7 Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 halocycloalkylcarbonyl, C3-C6 cycloalkenylcarbonyl, C3-C6 halocycloalkenylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, C1-C6 alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminothiocarbonyl, C1-C6 alkylthioC2-C6 alkylcarbonyl, and unselected. The phenyl C1-C2 alkyl, phenyl carbonyl, phenyl C1-C2 alkyl carbonyl, phenyl C2-C4 alkenyl carbonyl, phenoxy C1-C2 alkyl carbonyl, thiophene carbonyl, pyrazole carbonyl, quinoline carbonyl: halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl or substituted with 1-4 halogens, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy, CR 8 R 9 ; R 8 R 9 : Selected from hydrogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, and C1-C6 alkylCOOR, respectively, or in different forms. 10 COOR 10 CH2OR 11 CH2NR 12 R 13 CONR 12 R 13 A phenyl group that is unsubstituted or substituted by 1-4 independently selected from the following groups; a pyridyl group that is unsubstituted or substituted by 1-4 independently selected from the following groups; a halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl, COOR 10 CONR 12 R 13 ; R 10 : Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylcarbonyloxy-C2-C4 alkyl, unsubstituted or substituted by 1-4 independently selected from the following groups: benzyl, furanylene, thiazolemethylene, tetrahydrofuranylene or pyridinylene, where the following groups are halogens, CN, NO2, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C1-C8 haloalkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl; R 11 Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C3-C6 cycloalkylcarbonyl, C3-C6 halocycloalkylcarbonyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl, di(C1-C6)alkylaminosulfonyl, C1-C6 alkylaminocarbonyl, di(C1-C6)alkylaminocarbonyl, di(C1-C6)alkylaminothiocarbonyl, C1-C6 alkylthioC2-C6 alkylcarbonyl, unsubstituted or substituted by 1-4 independently selected from the following groups, phenyl, phenylC1 -C2 alkyl, phenyl C2-C4 alkenyl, phenyl carbonyl, phenyl C1-C2 alkyl carbonyl, phenoxy C1-C2 alkyl carbonyl, phenyl C2-C4 alkenyl carbonyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryl carbonyl, the following groups being halogen, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkoxy carbonyl, C1-C4 alkylthio, C1-C4 alkylsulfonyl or phenoxy groups independently substituted by 1-4 halogens, CN, NO2, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy or C1-C4 haloalkoxy; R 12 R 13 : Selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxycarbonylC1-C6 alkyl, SO2NH(C1-C6 alkyl) or SO2N(C1-C6 alkyl)(C1-C6 alkyl); X: C, O, S, NH, COO, CHNO, SO2NH, NHSO2 or unsubstituted; Z: CH2, CH(CH3), C(CH3)2; n is selected from 0, 1, 2, 3, 4, 5, and 6 respectively.

2. As described in claim 1 N -Phenyline pyrimidine dione derivatives, characterized in that... Including the following compounds: Compound L1: (E)-3-(1-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)methyl benzoate; Compound L2: (E)-4-(1-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)methyl benzoate; Compound L3: (E)-2-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methyl benzoate; Compound L4: (E)-3-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)methyl)ethyl benzoate; Compound L5: (E)-4-((((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methyl benzoate; Compound L6: (E)-3-(4-chloro-2-fluoro-5-((((1-(2-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L7: (E)-3-(4-chloro-2-fluoro-5-(((1-(3-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L8: (E)-3-(4-chloro-2-fluoro-5-((((1-(4-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L9: (E)-2-methoxybenzaldehyde o-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl) oxime; Compound L10: (E)-3-methoxybenzaldehyde o-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl) oxime; Compound L11: (E)-4-methoxybenzaldehyde o-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl) oxime; Compound L12: (E)-3-(4-chloro-2-fluoro-5-((((1-(2-fluorophenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L13: (E)-3-(4-chloro-2-fluoro-5-(((1-(2-fluoro-4-methoxyphenyl)ethylene)amino)oxy)carbonyl)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L14: 3-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclobutane-1-carboxylic acid methyl ester; Compound L15: (Z)-2-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L16: (E)-3-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L17: (E)-3-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L18: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L19: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid propyl ester; Compound L20: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-carboxylic acid isopropyl ester; Compound L21: 4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)-1-methylcyclohexane-1-carboxylic acid methyl ester; Compound L22: 2-(4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L23: (E)-2-(2-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L24: (E)-4-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)-imino)-2-methylcyclohex-2-ene-1-carboxylic acid ethyl ester; Compound L25: S-ethyl 4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L26: S-isopropyl4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L27: 4-((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzoyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L28: (E)-6-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl) nicotinic acid methyl ester; Compound L29: (E)-6-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)methylpyridinecarboxylate; Compound L30: Methyl(E)-5-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)pyridinecarboxylate; Compound L31: (E)-2-(1-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)methyl isonicotinic acid; Compound L32: (E)-5-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)furan-2-carboxylic acid methyl ester; Compound L33: (E)-5-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)methyl)thiophene-2-carboxylic acid methyl ester; Compound L34: (E)-5-(1-(((2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H-yl)benzoyl)oxy)imino)ethyl)thiophene-2-carboxylic acid methyl ester; Compound L35: (E)-3-(4-chloro-2-fluoro-5-((1-(((1-(3-methoxyphenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L36: (E)-3-(4-chloro-2-fluoro-5-((1-(((1-(4-methoxyphenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L37: (E)-2-methoxybenzaldehyde O-(2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxime; Compound L38: (E)-3-methoxybenzaldehyde O-(2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxime; Compound L39: (E)-4-methoxybenzaldehyde O-(2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxime; Compound L40: (E)-3-(1-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)ethyl)methyl benzoate; Compound L41: (E)-4-(1-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)ethyl)methyl benzoate; Compound L42: (E)-2-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)benzoate; Compound L43: (E)-3-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)benzoate; Compound L44: (E)-4-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)benzoate; Compound L45: (E)-3-(4-chloro-2-fluoro-5-((1-((1-(2-fluoro-4-methoxyphenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L46: (E)-3-(4-chloro-2-fluoro-5-((1-(((1-(2-fluorophenyl)ethylene)amino)oxy)-1-oxopropyl-2-yl)oxy)phenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione; Compound L47: 3-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclobutane-1-carboxylic acid methyl ester; Compound L48: (E)-2-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L49: (E)-3-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclopentane-1-carboxylic acid methyl ester; Compound L50: (E)-3-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L51: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid methyl ester; Compound L52: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid ethyl ester; Compound L53: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid propyl ester; Compound L54: 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-carboxylic acid propyl ester; Compound L55: S-ethyl 4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L56: S-propyl-4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyloxy)imino)cyclohexane-1-thiocarboxylic acid ester; Compound L57: S-isopropyl4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexane-1-thiocarbamate; Compound L58: 4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)-imino)-1-methylcyclohexane-1-carboxylic acid methyl ester; Compound L59: (E)-2-(2-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L60: 2-(4-((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)cyclohexyl)ethyl acetate; Compound L61: (E)-4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)-2-methylcyclohex-2-ene-1-carboxylic acid ethyl ester; Compound L62: (E)-4-(((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)-2,6-dimethylcyclohex-2-ene-1-carboxylic acid methyl ester; Compound L63: (E)-5-((((2-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)phenoxy)propionyl)oxy)imino)methyl)thiophene-2-carboxylic acid methyl ester.

3. As described in any one of claims 1-2 N The method for preparing phenylpyrimidine dione derivatives is characterized by, Includes the following steps: (1) Preparation of intermediate 3: NaH was dissolved in DMF, and intermediate 1 was slowly added under ice bath conditions. After stirring in an ice bath for 10 minutes, the mixture was brought to room temperature and stirred for 1 hour. Then, intermediate 2 was slowly added dropwise under ice bath conditions, followed by a reaction at room temperature for 2 hours. The resulting intermediate 3 was extracted with water and ethyl acetate, respectively, and obtained by column chromatography. Intermediate 1 was... The intermediate 2 is ; (2) Preparation of intermediate 5: Intermediate 4, ammonium chloride, and 90% ethanol solution were mixed and stirred, then heated to 80°C. Iron powder was then slowly added, and the reaction system was allowed to react at 80°C for 4 hours. The remaining iron powder was removed by filtration, and then the mixture was subjected to extraction, drying, and column chromatography to obtain intermediate 5. Intermediate 4 is... ; (3) Preparation of intermediate 6: Intermediates 3 and 5 were dissolved in acetic acid and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with water and ethyl acetate. The organic layer was dried by rotary evaporation to obtain intermediate 6, which did not require further purification and was directly added to the next step. (4) Preparation of intermediate 7: Intermediate 6 was dissolved in DMF, and then K2CO3 and R were added respectively. 1 I. Stir at room temperature for 4 hours. After the reaction is complete, extract repeatedly with a large amount of water and ethyl acetate, then dry with anhydrous sodium sulfate, and finally obtain intermediate 7 by column chromatography. (5) Preparation of intermediate 8: Intermediate 7 was dissolved in a mixed acid, and CrO3 was added in batches under ice bath conditions. The mixture was stirred for 8 hours, quenched with water, extracted with ethyl acetate, dried the organic layer, evaporated under vacuum, and finally obtained intermediate 8 by column chromatography. The mixed acid was composed of acetic acid and sulfuric acid in a volume ratio of AcOH:H2SO4 = 4:

1. (6) Preparation of target compounds L1–L34: Intermediate 8, DCC, DMAP and R 7 NOH was added to CH2Cl2, and the mixture was stirred at room temperature for 6 hours. After the reaction was completed, it was quenched with water by TLC, and then extracted. The target compounds L1–L34 were obtained by column chromatography. (7) Preparation of intermediate 11: Intermediates 9 and 10 were dissolved in potassium carbonate in DMF and stirred at room temperature for 4 hours. After the reaction was complete, they were extracted, dried, and subjected to column chromatography to obtain intermediate 11. Intermediate 9 was... The intermediate 10 is ; (8) Preparation of intermediate 12: After mixing and stirring intermediate 11, ammonium chloride and 90% ethanol solution, the temperature was raised to 80°C, and then iron powder was slowly added. After the reaction system was reacted at 80°C for 4 hours, the remaining iron powder was removed by filtration, and then intermediate 12 was obtained by extraction, drying and column chromatography. (9) Preparation of intermediate 13: Intermediates 3 and 12 were dissolved in acetic acid and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with water and ethyl acetate. The organic layer was dried by rotary evaporation to obtain intermediate 13, which did not require further purification and was directly introduced to the next step. (10) Preparation of intermediate 14: Intermediate 13 was dissolved in DMF, and then K2CO3 and R were added respectively. 1 I. Stir at room temperature for 4 hours. After the reaction is complete, extract repeatedly with a large amount of water and ethyl acetate, then dry with anhydrous sodium sulfate, and finally obtain intermediate 14 by column chromatography. (11) Preparation of intermediate 15: Intermediate 15 was dissolved in a mixed acid (volume ratio: AcOH:H2SO4:H2O = 2:1:1), heated to 100℃ and refluxed for 4 hours, then poured into ice and filtered to obtain the solid. Intermediate 15 could be obtained without further purification. (12) Preparation of target compounds E26–E40: Intermediate 15, DCC, DMAP and R 7 NOH was added to CH2Cl2, and the mixture was stirred at room temperature for 6 hours. After the reaction was complete as monitored by TLC, water was added to quench the reaction, followed by extraction. The target compounds L35–L63 were obtained by column chromatography.

4. As described in any one of claims 1-2 N Application of phenylpyrimidine dione derivatives in the preparation of herbicide for weed control.

5. A herbicidal composition, characterized in that, The herbicidal composition comprises a herbicidal effective amount of any one of claims 1-2. N -Phenylenidine dione derivatives; based on the total weight of the herbicidal composition, the N The content of phenylpyrimidine dione derivatives is 0.01-99% by weight.

6. The herbicidal composition according to claim 5, characterized in that, The N The content of phenylpyrimidine dione derivatives is 0.01-70% by weight.

7. The herbicidal composition according to claim 6, characterized in that, The N The content of phenylpyrimidine dione derivatives is 5-60% by weight.

8. A herbicide, characterized in that, The herbicide comprises an active ingredient and excipients, wherein the active ingredient is as described in claim 1 or 2. N - A phenylimide derivative or the herbicidal composition of claim 4; the content of the active ingredient is 1-99.99% by weight, based on the total weight of the herbicide.

9. The herbicide as described in claim 8, characterized in that, The content of the active ingredient is 5-90% by weight.

10. The herbicide as described in claim 9, characterized in that, The excipients are at least one of emulsifiers, dispersants, wetting agents, spreading agents, stabilizers, defoamers, synergists, penetrants, adhesives, safeners, carriers, surfactants, and fillers; the formulation of the herbicide is selected from at least one of emulsifiable concentrates, suspension concentrates, wettable powders, powders, granules, aqueous solutions, mother liquors, and mother powders.

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