Chloro pyrimidine benzamide derivative as well as preparation method and application thereof

Abstract

The invention relates to a pesticide herbicide, and discloses a chloropyrimidine benzamide derivative as well as a preparation method and application thereof. Structural formula of chloropyrimidine benzamide derivative is shown in the specification

Description

Technical Field

[0001] This invention relates to the field of pesticides and herbicides, specifically disclosing a chlorpyrimethanil benzamide derivative, its preparation method, and its application. Background Technology

[0002] Branched-chain amino acids in plants are mainly synthesized by the plant itself and are one of the basic building blocks of protein synthesis. Several key proteins in the branched-chain amino acid synthesis pathway include acetohydroxyacid synthase (AHAS), ketolacid reductoisomerase (KARI), and dihydroxyacid dehydratase (DHAD).

[0003] Currently, there are over 50 herbicides targeting AHAs, most of which exhibit highly effective and broad-spectrum herbicidal activity. KARI is another protein in the branched-chain amino acid synthesis pathway, occurring in the presence of metal ions (Mg). 2+ Catalyzed by the cofactor NADPH, 2-acetolactate or 2-acetyl-2-hydroxybutyrate is reduced to 2,3-dihydroxy-3-methylbutanoate or 2,3-dihydroxy-3-methylpentanoate. This inhibits the biological activity of KARI, blocks the synthesis of branched-chain amino acids, affects protein synthesis, and leads to the disruption of physiological and biochemical processes in plants, resulting in weed death.

[0004] With the long-term reliance on single-use herbicides, weed resistance has become an increasingly serious problem, making the development of novel herbicides with new mechanisms of action an urgent need for resistant weed control. Currently, there are no commercially available herbicide molecules targeting KARIs, and existing acetylhydroxy acid reductase (KARI) inhibitors generally suffer from simple molecular structures and low biological activity. Therefore, developing novel KARI-targeting herbicides with stronger herbicidal activity and simpler synthetic processes is of great significance for overcoming the current bottleneck in resistant weed control. Summary of the Invention

[0005] Based on the structure of the KARI protein, this invention employs a structure-based drug molecule design method to design and synthesize a novel class of chlorpyrimethamine benzamide derivatives.

[0006] Therefore, the purpose of this invention is to provide a novel class of chlorpyrimethanil benzamide derivatives that exhibit high herbicidal activity against broadleaf weeds and grass weeds.

[0007] To achieve the above objectives, a first aspect of the present invention provides a method for preparing chloropyrimidine benzamide derivatives having the structure shown in Formula I:

[0008] Formula I

[0009] Among them, R 1 Selected from H, halogens, C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkyl, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C 12 Heterocyclic rings;

[0010] R 2 Selected from H, halogens, C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkyl, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C 12 Heterocyclic rings;

[0011] R 3 Selected from H, halogens, C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkyl, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C 12 Heterocyclic rings;

[0012] X is selected from NH, O, S;

[0013] X is located at any substitution position on the aromatic ring;

[0014] R 4 Selected from H, halogen, hydroxyl, amino, mercapto, cyano, nitro, phenyl, pyridyl, C1-C 12 Alkyl groups, halogen-substituted C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkoxy groups, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C8 heterocycles;

[0015] R 5 Any group selected from Q1-Q18 below

[0016]

[0017] Among them, R in Q1-Q18 6 -R 23 Each of the following is independently selected from H, halogen, hydroxyl, amino, mercapto, cyano, nitro, phenyl, pyridyl, C1-C12 alkyl, halogen-substituted C1-C12 alkyl, C1-C12 alkoxy, halogen-substituted C1-C12 alkoxy, phenyl substituted or unsubstituted by C1-C12 alkyl and / or halogen, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, phenyl substituted by C1-C12 alkoxy, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, and C3-C8 heterocycles substituted or unsubstituted by C1-C12 alkyl and / or halogen; n = 0, 1, 2, 3, 4, 5, 6.

[0018] The terminology used in this invention has the following interpretations.

[0019] “C1-C 12"alkyl" refers to an alkyl group with a total number of carbon atoms of 1-12, including straight-chain alkyl, branched alkyl, or cycloalkyl. For example, it can be a straight-chain alkyl, branched alkyl, or cycloalkyl group with a total number of carbon atoms of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclobutyl, methylcyclobutyl, ethylcyclobutyl, cyclopentyl, methylcyclopentyl, ethylcyclopentyl, cyclohexyl, methylcyclohexyl, ethylcyclohexyl, etc.

[0020] In this invention, "C1-C" 12 "alkoxy group" refers to an alkoxy group with 1-12 carbon atoms, such as methyloxy, ethyloxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, n-hexyloxy, cyclopropyloxy, methylcyclopropyloxy, ethylcyclopropyloxy, cyclopentyloxy, methylcyclopentyloxy, and cyclohexyloxy.

[0021] In this invention, "C1-C" 12 "Alkylamino" indicates an amino group with alkyl substitution having 1-12 carbon atoms, which can be mono- and / or dialkyl-substituted, wherein the alkyl group can be the same and / or different when dialkyl-substituted.

[0022] In this invention, "C2-C6 alkenyl" refers to a monoalkenyl, dienyl, or polyalkenyl group having 1-6 carbon atoms, such as vinyl, n-propenyl, isopropenyl, n-butenyl, n-dibutenyl, isobutenyl, tert-butenyl, n-pentenyl, 1,3-pentadienyl, isopentenyl, n-hexenyl, 1,3-hexadienyl, cyclopropenyl, methylcyclopropenyl, ethylcyclopropenyl, cyclopentenyl, methylcyclopentenyl, and cyclohexenyl.

[0023] In this invention, "C2-C6 alkynyl" refers to a mono-alkynyl, di-alkynyl, or poly-alkynyl group having 1-6 carbon atoms. Examples include ethynyl, n-propynyl, isopropynyl, n-butynyl, n-dibutynyl, isobutynyl, tert-butynyl, n-pentynyl, 1,3-pentadiynyl, isopentenynyl, n-hexynyl, 1,3-hexadiynyl, cyclopropynyl, methylcyclopropynyl, ethylcyclopropynyl, cyclopentynyl, methylcyclopentynyl, and cyclohexynyl.

[0024] In this invention, the term "substituted or unsubstituted C3-C8 heterocycle" refers to a heterocycle containing at least one of N, O, and S.

[0025] In this invention, "halogen" means at least one element selected from fluorine, chlorine, bromine, and iodine.

[0026] The present invention does not particularly limit the method of synthesizing the derivative containing chloropyrimidine benzamide as shown in formula (I). Those skilled in the art can obtain suitable methods for preparing the derivative shown in formula (I) by combining the compound structure provided by the present invention with the synthesis methods in the field of chemistry. The present invention will not elaborate on these methods here.

[0027] The second aspect of the present invention provides a method for preparing the compound described in the first aspect, using the following synthetic route, wherein the position and type of substituents are changed according to the specific compound:

[0028] Synthetic route (1)

[0029] ;

[0030] Synthetic route (2)

[0031] ;

[0032] Synthetic route (3)

[0033] .

[0034] Specifically, in synthetic routes (1), (2), and (3),

[0035] In step a, raw material II-1, III-1 or IV-1 is dissolved in a solvent, acid or base is added, and then 2-methanesulfonylpyrimidine or 2-chloropyrimidine substituted product is added. The mixture is heated and stirred at 50℃-110℃. After the reaction is completed, the reaction is quenched, extracted, the organic phase is concentrated, and column chromatography is used to obtain intermediate II-2, III-2 or IV-2.

[0036] In step b, intermediate II-2, III-2 or IV-2 is dissolved in a solvent, an oxidant is added, and the mixture is stirred at room temperature. After the reaction is complete, the solvent is removed, the pH is adjusted to precipitate the product, and the mixture is filtered to obtain intermediate II-3, III-3 or IV-3.

[0037] In step c, intermediates II-3, III-3, or IV-3 are dissolved in thionyl chloride, and a small amount of N,N-dimethylformamide is added as a catalyst. The mixture is stirred at 70-80°C until the reaction is complete. After evaporating the solvent, intermediates II-4, III-4, or IV-4 are obtained.

[0038] In step d, amines with different substituents are dissolved in a solvent, a base is added, and intermediates II-4, III-4, or IV-4 are added under ice bath conditions. After the reaction is complete, column chromatography is used to obtain the final product II-5, III-5, or IV-5.

[0039] Specifically, the solvent in step ad is selected from one of water, N,N-dimethylformamide, acetonitrile, N,N-diethylacetamide, dichloromethane, 1,4-dioxane, toluene, dimethyl sulfoxide, acetic acid, methanol, ethanol, and tert-butanol.

[0040] A third aspect of the present invention provides the use of the compound in the preparation of pesticide herbicides.

[0041] Specifically, the target weeds controlled by the herbicide are selected from at least one of the following: grass weeds, broadleaf weeds, and sedge weeds.

[0042] More specifically, the broadleaf weeds are at least one of the following: amaranth, lamb's quarters, velvetleaf, rice-leaf grass, cassia, morning glory, cocklebur, reverse-branch amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, water bamboo leaf, wild arrowhead, water plantain, rain-flower, dayflower, duck tongue grass, etc., and sedges: firefly rush, and sedge of different species; the grass weeds are at least one of the following: foxtail, barnyard grass, barnyard grass, crabgrass, jointed goatgrass, wild oat, wild oat, Japanese wild oat, amaranth, lambsquarters, and reverse-branch amaranth.

[0043] A fourth aspect of the present invention provides a pesticide herbicide composed of an active ingredient and excipients, wherein the active ingredient includes at least one of the compounds, and the content of the active ingredient is 1 to 99.9999% by weight; preferably, the content of the active ingredient is 1 to 50% by weight.

[0044] Specifically, the formulation of the pesticide herbicide is selected from one of the following: emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, poison bait, mother liquor, and mother powder.

[0045] This invention has the following advantages: First, the compounds of this invention exhibit novel mechanisms of action in weed control. They contain chlorpyrifos-benzamide derivatives that act on acetylhydroxy acid reductase (KARI), a process not previously reported. In particular, the compounds of this invention possess high weed-control activity; the chlorpyrifos-benzamide derivatives have a strong inhibitory effect on weeds, and some compounds show comparable inhibitory effects to bispyribac-sodium, demonstrating significant application value.

[0046] Secondly, the compounds of this invention have simple structures and are easy to prepare. The chlorpyrimethamine benzamide derivatives of this invention have simple chemical formulas and are easy to prepare. Furthermore, the compounds of this invention, as herbicides, are safe for mammals. Chlorpyrimethamine benzamide derivatives are herbicides designed to target branched-chain amino acids, which are not present in mammals, thus ensuring safety for mammals. Detailed Implementation

[0047] Example 1

[0048] The following synthetic route was used to synthesize compound H25049.

[0049]

[0050] Synthesis of intermediate of formula II-2a

[0051] 2-Chloro-3-hydroxybenzaldehyde (20 mmol) was dissolved in N,N-dimethylformamide, and potassium carbonate (40 mmol) and 2,5-dichloropyrimidine (40 mmol) were added. The mixture was heated to 50 °C and reacted for two hours. The reaction was monitored by TLC. After the reaction was complete, hydrochloric acid was added to quench the reaction, and the mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride water, and the organic phase was collected, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to give intermediate II-2a in 92% yield.

[0052] Synthesis of intermediate of formula II-3a

[0053] Intermediate II-2a (10 mmol) was dissolved in a mixture of tert-butanol and water. Sodium dihydrogen phosphate (60 mmol), 2-methyl-2-butene (100 mmol), and finally sodium chlorite (30 mmol) were added. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the tert-butanol was evaporated to dryness, and the pH was adjusted until a precipitate formed. The precipitate was then filtered to give intermediate II-3a in 90% yield.

[0054] Synthesis of intermediate of formula II-4a

[0055] Intermediate II-3a (5 mmol) was dissolved in thionyl chloride, and a few drops of N,N-dimethylformamide were added. The temperature was raised to 78 °C, and the reaction was carried out for four hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was evaporated to give intermediate II-4a in 98% yield.

[0056] Synthesis of compound H25049

[0057] 4-Amino-2,6-difluoropyridine (2 mmol) was dissolved in dichloromethane, triethylamine was added, and intermediate II-4a (2.1 mmol) was slowly added under ice bath conditions. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and column chromatography was performed to give compound H25049 in 90% yield.

[0058] Example 2

[0059] The following synthetic route was used to synthesize compound H25473.

[0060]

[0061] Synthesis of intermediate of formula II-2b

[0062] 2-Chloro-4-hydroxybenzaldehyde (20 mmol) was dissolved in N,N-dimethylformamide, and potassium carbonate (40 mmol) and 2,5-dichloropyrimidine (40 mmol) were added. The mixture was heated to 50 °C and reacted for two hours. The reaction was monitored by TLC. After the reaction was complete, hydrochloric acid was added to quench the reaction, and the mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride water, and the organic phase was collected. The phase was dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to give intermediate II-2b in 85% yield.

[0063] Synthesis of intermediate of formula II-3b

[0064] Intermediate II-2b (10 mmol) was dissolved in a mixture of tert-butanol and water. Sodium dihydrogen phosphate (60 mmol), 2-methyl-2-butene (100 mmol), and sodium chlorite (30 mmol) were added. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the tert-butanol was evaporated to dryness, and the pH was adjusted until a precipitate formed. The precipitate was then filtered to give intermediate II-3b in 88% yield.

[0065] Synthesis of intermediate of formula II-4b

[0066] Intermediate II-3b (5 mmol) was dissolved in thionyl chloride, and a few drops of N,N-dimethylformamide were added. The temperature was raised to 78 °C, and the reaction was carried out for four hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was evaporated to give intermediate II-4b in 98% yield.

[0067] Synthesis of compound H25473

[0068] Isoxazol-5-methylamine (2 mmol) was dissolved in dichloromethane, triethylamine was added, and intermediate II-4b (2.1 mmol) was slowly added under ice bath conditions. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and column chromatography was used to give compound H25473 in 95% yield.

[0069] Example 3

[0070] The following synthetic route was used to synthesize compound H25405.

[0071]

[0072] Synthesis of intermediate of formula III-2a

[0073] 2-Chloro-3-mercaptobenzaldehyde (20 mmol) was dissolved in N,N-dimethylformamide, and potassium carbonate (40 mmol) and 2,5-dichloropyrimidine (40 mmol) were added. The mixture was heated to 50 °C and reacted for two hours. The reaction was monitored by TLC. After the reaction was complete, hydrochloric acid was added to quench the reaction, and the mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride water, and the organic phase was collected. The phase was dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to give intermediate III-2a in 80% yield.

[0074] Synthesis of intermediate of formula III-3a

[0075] Intermediate III-2a (10 mmol) was dissolved in a mixture of tert-butanol and water. Sodium dihydrogen phosphate (60 mmol), 2-methyl-2-butene (100 mmol), and sodium chlorite (30 mmol) were added. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the tert-butanol was evaporated to dryness, and the pH was adjusted until a precipitate formed. The precipitate was then filtered to give intermediate III-3a in 80% yield.

[0076] Synthesis of intermediate of formula III-4a

[0077] Intermediate III-3a (5 mmol) was dissolved in thionyl chloride, and a few drops of N,N-dimethylformamide were added. The temperature was raised to 78 °C, and the reaction was carried out for four hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was evaporated to give intermediate III-4a in 97% yield.

[0078] Synthesis of compound H25405

[0079] 4-Amino-2,6-difluoropyridine (2 mmol) was dissolved in dichloromethane, triethylamine was added, and intermediate III-4a (2.1 mmol) was slowly added under ice bath conditions. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and column chromatography was used to give compound H25405 in 91% yield.

[0080] Example 4

[0081] The following synthetic route was used to synthesize compound H25497.

[0082]

[0083] Synthesis of intermediate of formula III-2b

[0084] 2-Chloro-4-mercaptobenzaldehyde (20 mmol) was dissolved in N,N-dimethylformamide, and potassium carbonate (40 mmol) and 2,5-dichloropyrimidine (40 mmol) were added. The mixture was heated to 50 °C and reacted for two hours. The reaction was monitored by TLC. After the reaction was complete, hydrochloric acid was added to quench the reaction, and the mixture was poured into water, extracted with ethyl acetate, washed with saturated sodium chloride water, and the organic phase was collected. The phase was dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to give intermediate III-2b in 77% yield.

[0085] Synthesis of intermediate of formula III-3b

[0086] Intermediate III-2b (10 mmol) was dissolved in a mixture of tert-butanol and water. Sodium dihydrogen phosphate (60 mmol), 2-methyl-2-butene (100 mmol), and sodium chlorite (30 mmol) were added. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the tert-butanol was evaporated, and the pH was adjusted until a precipitate formed. The precipitate was then filtered to give intermediate III-3b in 70% yield.

[0087] Synthesis of intermediate of formula III-4b

[0088] Intermediate III-3b (5 mmol) was dissolved in thionyl chloride, and a few drops of N,N-dimethylformamide were added. The temperature was raised to 78 °C, and the reaction was carried out for four hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was evaporated to give intermediate III-4b in 95% yield.

[0089] Synthesis of compound H25497

[0090] Isoxazol-5-methylamine (2 mmol) was dissolved in dichloromethane, triethylamine was added, and intermediate III-4b (2.1 mmol) was slowly added under ice bath conditions. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and column chromatography was used to give compound H25497 in 90% yield.

[0091] Example 5

[0092] The following synthetic route was used to synthesize compound H25429.

[0093]

[0094] Synthesis of Formula IV-2a intermediate

[0095] 2-Chloro-3-aminobenzaldehyde (20 mmol) was dissolved in 1,4-dioxane, and 2,5-dichloropyrimidine (30 mmol) was added. Acetic acid (3 mL) was added, and the mixture was heated to 110 °C and reacted overnight. The reaction was monitored by TLC. After the reaction was complete, the mixture was poured into water, extracted with DCM, washed with saturated sodium chloride water, and the organic phase was collected, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to give intermediate IV-2a in 88% yield.

[0096] Synthesis of Formula IV-3a intermediate

[0097] Intermediate IV-2a (10 mmol) was dissolved in a mixture of tert-butanol and water. Sodium dihydrogen phosphate (60 mmol), 2-methyl-2-butene (100 mmol), and finally sodium chlorite (30 mmol) were added. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the tert-butanol was evaporated to dryness, and the pH was adjusted until a precipitate formed. The precipitate was then filtered to give intermediate IV-3a in 92% yield.

[0098] Synthesis of Formula IV-4a intermediate

[0099] Intermediate IV-3a (5 mmol) was dissolved in thionyl chloride, and a few drops of N,N-dimethylformamide were added. The temperature was raised to 78 °C, and the reaction was carried out for four hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was evaporated to give intermediate IV-4a in 90% yield.

[0100] Synthesis of compound H25429

[0101] 4-Amino-2,6-difluoropyridine (2 mmol) was dissolved in dichloromethane, triethylamine was added, and intermediate IV-4a (2.1 mmol) was slowly added under ice bath conditions. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and column chromatography was used to give compound H25429 in 85% yield.

[0102] Example 6

[0103] The following synthetic route was used to synthesize compound H25521.

[0104]

[0105] Synthesis of Formula IV-2b intermediate

[0106] 2-Chloro-4-aminobenzaldehyde (20 mmol) was dissolved in 1,4-dioxane, and 2,5-dichloropyrimidine (30 mmol) was added. Acetic acid (3 mL) was added, and the mixture was heated to 110 °C and reacted overnight. The reaction was monitored by TLC. After the reaction was complete, the mixture was poured into water, extracted with DCM, washed with saturated sodium chloride water, and the organic phase was collected, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to give intermediate IV-2b in 82% yield.

[0107] Synthesis of Formula IV-3b intermediate

[0108] Intermediate IV-2b (10 mmol) was dissolved in a mixture of tert-butanol and water. Sodium dihydrogen phosphate (60 mmol), 2-methyl-2-butene (100 mmol), and finally sodium chlorite (30 mmol) were added. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the tert-butanol was evaporated to dryness, and the pH was adjusted until a precipitate formed. The precipitate was then filtered to give intermediate IV-3b in 80% yield.

[0109] Synthesis of Formula IV-4b intermediate

[0110] Intermediate IV-3b (5 mmol) was dissolved in thionyl chloride, and a few drops of N,N-dimethylformamide were added. The temperature was raised to 78 °C, and the reaction was carried out for four hours. The reaction progress was monitored by TLC. After the reaction was completed, the solvent was evaporated to obtain intermediate IV-4b in 90% yield.

[0111] Synthesis of compound H25521

[0112] Isoxazol-5-methylamine (2 mmol) was dissolved in dichloromethane, triethylamine was added, and intermediate IV-4b (2.1 mmol) was slowly added under ice bath conditions. The mixture was stirred at room temperature for two hours, and the reaction was monitored by TLC. After the reaction was complete, the solvent was evaporated, and column chromatography was used to give compound H25521 in 91% yield.

[0113] The chloropyrimidine benzamide derivatives of the present invention were synthesized according to the above method. Table 1 lists the structural characterization data of some compounds of the present invention.

[0114] Table 1 Physical properties and spectral characterization of the compounds

[0115]

[0116]

[0117]

[0118] Example 5: Seed germination experiment (1 / 2 MS medium method)

[0119] Using 10 Ten vernalized seeds were sown in each 10cm sterile square Petri dish. Each dish contained 30 mL of sterile half-strength Murashige and Skoog (MS) solutions (2.2 g / L MS salt, 10 g / L sucrose, pH 5.7-5.8, and 8 g / L agar) and a chemical at concentrations of 12.5 mg / L, 25 mg / L, 50 mg / L, 100 mg / L, and 200 mg / L (usually dissolved in DMSO). Dishes containing DMSO served as blank controls. The dishes were incubated vertically in darkness for 7 days. After 7 days, stem and root lengths were measured. Table 2 lists the inhibition rates of some compounds on seed stem length, and Table 3 lists the inhibition rates of some compounds on seed root length.

[0120] Table 2 shows the inhibition rates of some compounds on seed stem length (concentration: µg / mL).

[0121]

[0122] Table 3 shows the inhibition rates of some compounds on seed root elongation (concentration: µg / mL).

[0123]

[0124] Example 6:

[0125] Preliminary screening experiment (pot method): The test targets were foxtail grass, barnyard grass, angelica sinensis, and amaranth retroflexus. 7cm inner diameter flowerpots were filled with composite soil (vermiculite:seedling substrate = 1:2, v / v) to 3 / 4 full. The above four weed targets (germination rate ≥ 85%) were directly sown, covered with 0.2cm of soil, and left to grow until the weeds reached approximately the 3-leaf stage. Each compound was applied at a dosage of 300 g ai / ha using an automatic sprayer. After the pesticide solution on the crop leaves dried, the plants were transferred to a greenhouse for cultivation (28℃-32℃, 70% humidity). Results were collected after 21 days.

[0126] Investigation Methods: After 30 days of experimental treatment, the symptoms of damage and growth inhibition of the target plants were visually observed, and the fresh weight of the aboveground parts was measured. The fresh weight inhibition rate (%) was calculated, and the control efficacy (%) was expressed as the fresh weight inhibition rate. Fresh weight inhibition rate (%) = (control fresh weight - treatment fresh weight) / control fresh weight × 100. The results are shown in Table 4.

[0127] Table 4. Herbicidal activity inhibition rate (%) of some compounds (dose 300 g ai / ha)

[0128]

[0129] Combining the results of seed germination inhibition experiments and post-emergence foliar spray herbicidal activity tests, we discovered for the first time that chlorpyrifos benzamide derivatives possess excellent herbicidal activity, and also confirmed that KARI can serve as a novel herbicide target. Currently, there are no commercially available inhibitors targeting KARI proteins; therefore, we selected bispyribac-sodium, a commercially available herbicide targeting ALS that also follows a branched-chain amino acid synthesis pathway, as a positive control.

[0130] The preliminary screening data for herbicides above show that some compounds, such as H25049, H25400, H25550, H25597, and H25622, exhibit good inhibitory effects against weeds such as barnyard grass, foxtail grass, eclipta prostrata, and amaranth. Furthermore, their performance is comparable to the positive control herbicide bispyribac-sodium. Therefore, these compounds have promising application prospects.

[0131] In summary, the chlorpyrimethamine benzamide derivatives described in this invention have the characteristics of simple structure, convenient preparation, novel mode of action, low toxicity, and high activity, and show good inhibitory effects on a variety of weeds, making them worthy of further research and development.

[0132] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A compound of a chloropyrimidine benzamide derivative, characterized in that, It has the structure shown in Formula I. Equation I; Among them, R 1 Selected from H, halogens, C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkyl, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C 12 Heterocyclic rings; R 2 Selected from H, halogens, C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkyl, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C 12 Heterocyclic rings; R 3 Selected from H, halogens, C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkyl, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, pyrimidinyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C 12 Heterocyclic rings; X is selected from NH, O, S; X is located at any substitution position on the aromatic ring; R 4 Selected from H, halogen, hydroxyl, amino, mercapto, cyano, nitro, phenyl, pyridyl, C1-C 12 Alkyl groups, halogen-substituted C1-C 12 Alkyl, C1-C 12 Alkoxy groups, C1-C groups substituted with halogens 12 Alkoxy groups, composed of C1-C 12 Alkyl and / or halogen-substituted or unsubstituted phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazole, C1-C 12 Alkoxy-substituted phenyl, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazole, and C1-C 12 Alkyl and / or halogen-substituted or unsubstituted C3-C8 heterocycles; R 5 Selected from any group from Q1-Q18 below; ； Among them, R in Q1-Q18 6 -R 23 Each of the following is independently selected from H, halogen, hydroxyl, amino, mercapto, cyano, nitro, phenyl, pyridyl, C1-C12 alkyl, C1-C12 alkyl substituted with halogen, C1-C12 alkoxy, C1-C12 alkoxy substituted with halogen, phenyl substituted with or unsubstituted with C1-C12 alkyl and / or halogen, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, phenyl substituted with C1-C12 alkoxy, benzyl, naphthyl, pyridyl, furanyl, thiophene, pyrazolyl, imidazolyl, and C3-C8 heterocycles substituted with or unsubstituted with C1-C12 alkyl and / or halogen; n=0,1,2,3,4,5,6。 2. The compound according to claim 1, characterized in that, Compounds of formulas I-1, I-2, I-3, and I-4: Equation I-1; Compound H25O49:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25050:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Cl, R 5 for ; Compound H25051:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For OH, R 5 for ; Compound H25052:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Br, R 5 for ; Compound H25053:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Br, R 5 for ; Compound H25054:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25055:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25056:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25057:R 1 For H, R 2 For H, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25058:R 1 For H, R 2 CH3, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25059:R 1 For H, R 2 For Br, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25072:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25O64:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25O61:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25O66:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25068:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25073:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25075:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25077:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25400:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25401:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H254O2:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H254O3:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25404:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25405:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25406:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Cl, R 5 for ; Compound H25407:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For OH, R 5 for ; Compound H25408:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Br, R 5 for ; Compound H25409:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Br, R 5 for ; Compound H25410:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25411:R 1 For Cl, R 2 For Cl, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25412:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25413:R 1 For H, R 2 For H, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25414:R 1 For H, R 2 CH3, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25415:R 1 For H, R 2 For Br, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25416:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25417:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25418:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25419:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25420:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25421:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25422:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25O423:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25424:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25425:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25426:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25427:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25428:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25429:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25430:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Cl, R 5 for ; Compound H25431:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For OH, R 5 for ; Compound H25432:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Br, R 5 for ; Compound H25433:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Br, R 5 for ; Compound H25434:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25435:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25436:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25437:R 1 For H, R 2 For H, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25438:R 1 For H, R 2 CH3, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25439:R 1 For H, R 2 For Br, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25440:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25441:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25442:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25443:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25444:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25445:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25446:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25447:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25448:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25449:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25450:R 1 For H, ; R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25451:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25452:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Equation I-2; Compound H25453:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25454:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Cl, R 5 for ; Compound H25455:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For OH, R 5 for ; Compound H25456:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Br, R 5 for ; Compound H25457:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Br, R 5 for ; Compound H25458:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25459:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25460:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25461:R 1 For H, R 2 For H, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25462:R 1 For H, R 2 CH3, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25463:R 1 For H, R 2 For Br, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25464:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25465:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25466:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25467:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25468:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25469:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25470:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25471:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25472:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25473:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25474:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25475:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25476:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25477:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25478:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Cl, R 5 for ; Compound H25479:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For OH, R 5 for ; Compound H25480:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Br, R 5 for ; Compound H25481:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Br, R 5 for ; Compound H25482:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25483:R 1 For Cl, R 2 For Cl, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25484:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25485:R 1 For H, R 2 For H, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25486:R 1 For H, R 2 CH3, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25487:R 1 For H, R 2 For Br, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25488:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25489:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25490:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25491:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25492:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25493:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25494:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25495:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25496:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25497:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25498:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25499:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25500:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25501:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25502:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Cl, R 5 for ; Compound H25503:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For OH, R 5 for ; Compound H25504:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Br, R 5 for ; Compound H25505:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Br, R 5 for ; Compound H25506:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25507:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25508:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25509:R 1 For H, R 2 For H, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25510:R 1 For H, R 2 CH3, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25511:R 1 For H, R 2 For Br, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25512:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25513:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25514:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25515:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25516:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25517:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25518:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25519:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25520:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25521:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25522:R 1 For H, ; R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25523:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25524:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Equation I-3; Compound H25525:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25526:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Cl, R 5 for ; Compound H25527:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For OH, R 5 for ; Compound H25528:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Br, R 5 for ; Compound H25529:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Br, R 5 for ; Compound H25530:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25531:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25532:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25533:R 1 For H, R 2 For H, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25534:R 1 For H, R 2 CH3, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25535:R 1 For H, R 2 For Br, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25536:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25537:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25538:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25539:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25540:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25541:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25542:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25543:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25544:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25545:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25546:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25547:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25548:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25549:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25550:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Cl, R 5 for ; Compound H25551:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For OH, R 5 for ; Compound H25552:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Br, R 5 for ; Compound H25553:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Br, R 5 for ; Compound H25554:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25555:R 1 For Cl, R 2 For Cl, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25556:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25557:R 1 For H, R 2 For H, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25558:R 1 For H, R 2 CH3, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25559:R 1 For H, R 2 For Br, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25560:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25561:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25562:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25563:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25564:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25565:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25566:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H250567:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25568:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25569:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25570:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25571:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25572:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25573:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25574:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Cl, R 5 for ; Compound H25575:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For OH, R 5 for ; Compound H25576:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Br, R 5 for ; Compound H25577:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Br, R 5 for ; Compound H25578:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25579:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25580:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25581:R 1 For H, R 2 For H, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25582:R 1 For H, R 2 CH3, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25583:R 1 For H, R 2 For Br, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25584:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25585:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25586:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25587:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25588:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25589:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25590:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25591:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25592:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25593:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25594:R 1 For H, ; R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25595:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25596:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Equation I-4; Compound H25597:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25598:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Cl, R 5 for ; Compound H25599:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For OH, R 5 for ; Compound H25600:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is O, R 4 For Br, R 5 for ; Compound H25601:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Br, R 5 for ; Compound H256O2:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H256O3:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H256O4:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25605:R 1 For H, R 2 For H, R 3 For Cl, X is O, R 4 For Cl, R 5 for ; Compound H25606:R 1 For H, R 2 CH3, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25607:R 1 For H, R 2 For Br, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25608:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25609:R 1 For H, R 2 For F, R 3 H is H, X is O, R is O 4 For F, R 5 for ; Compound H25610:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25611:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25612:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25613:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25614:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25615:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25616:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25617:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25618:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25619:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25620:R 1 For H, R 2 For Cl, R 3 H is H, X is O, R is O 4 For Cl, R 5 for ; Compound H25621:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25622:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Cl, R 5 for ; Compound H25623:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For OH, R 5 for ; Compound H25624:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is S, R 4 For Br, R 5 for ; Compound H25625:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Br, R 5 for ; Compound H25626:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25627:R 1 For Cl, R 2 For Cl, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25628:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25629:R 1 For H, R 2 For H, R 3 Let Cl be S and R be R. 4 For Cl, R 5 for ; Compound H25630:R 1 For H, R 2 CH3, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25631:R 1 For H, R 2 For Br, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25632:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25633:R 1 For H, R 2 For F, R 3 Let H be S, X be S, and R be R. 4 For F, R 5 for ; Compound H25634:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25635:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25636:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25637:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25638:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25O639:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25640:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25641:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25642:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25643:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25644:R 1 For H, R 2 For Cl, R 3 Let H be S, X be S, and R be R. 4 For Cl, R 5 for ; Compound H25645:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25646:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Cl, R 5 for ; Compound H25647:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For OH, R 5 for ; Compound H25648:R 1 For OCH3, R 2 For H, R 3 For OCH3, X is NH, R 4 For Br, R 5 for ; Compound H25649:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Br, R 5 for ; Compound H25650:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25651:R 1 For Cl, R 2 For Cl, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25652:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25653:R 1 For H, R 2 For H, R 3 For Cl, X is NH, R 4 For Cl, R 5 for ; Compound H25654:R 1 For H, R 2 CH3, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25655:R 1 For H, R 2 For Br, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25656:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25657:R 1 For H, R 2 For F, R 3 H is H, X is NH, R 4 For F, R 5 for ; Compound H25658:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25659:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25660:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25661:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25662:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25663:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25664:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25665:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25666:R 1 For H, ; R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25667:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for ; Compound H25668:R 1 For H, R 2 For Cl, R 3 H is H, X is NH, R 4 For Cl, R 5 for .

3. A method for preparing the compound according to claim 1 or 2, characterized in that, The following synthetic route was used for the synthesis. The position and type of substituents were changed according to the specific compound: Synthetic route (1) ； Synthetic route (2) ； Synthetic route (3) 。 4. The preparation method according to claim 3, characterized in that, In the synthetic routes (1), (2), and (3), In step a, raw material II-1, III-1 or IV-1 is dissolved in a solvent, acid or base is added, and then 2-methanesulfonylpyrimidine or 2-chloropyrimidine substituted product is added. The mixture is heated and stirred at 50℃-110℃. After the reaction is completed, the reaction is quenched, extracted, the organic phase is concentrated, and column chromatography is used to obtain intermediate II-2, III-2 or IV-2. In step b, intermediate II-2, III-2 or IV-2 is dissolved in a solvent, an oxidant is added, and the mixture is stirred at room temperature. After the reaction is complete, the solvent is removed, the pH is adjusted to precipitate the product, and the mixture is filtered to obtain intermediate II-3, III-3 or IV-3. In step c, intermediates II-3, III-3, or IV-3 are dissolved in thionyl chloride, a small amount of N,N-dimethylformamide is added as a catalyst, and the mixture is stirred at 70-80°C until the reaction is complete. After evaporating the solvent, intermediates II-4, III-4, or IV-4 are obtained. In step d, amines with different substituents are dissolved in a solvent, a base is added, and intermediates II-4, III-4, or IV-4 are added under ice bath conditions. After the reaction is complete, column chromatography is used to obtain the final product II-5, III-5, or IV-5.

5. The preparation method according to claim 4, characterized in that, The solvent in step ad is selected from water, N,N-dimethylformamide, acetonitrile, N,N-diethylacetamide, dichloromethane, 1,4-dioxane, toluene, dimethyl sulfoxide, acetic acid, methanol, ethanol, tert-butanol, and acetone.

6. The use of the compound according to claim 1 or 2 in the preparation of pesticide herbicides.

7. The application as described in claim 6, characterized in that, The herbicide targets at least one weed selected from grass weeds, broadleaf weeds, and sedge weeds.

8. The application as described in claim 7, characterized in that, The broadleaf weeds are at least one of the following: amaranth, lamb's quarters, velvetleaf, rice-leaf grass, cassia, morning glory, cocklebur, reverse-branch amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, water bamboo leaf, wild arrowhead, water plantain, rain-flower, dayflower, duck tongue grass, etc., and sedges: firefly rush, and sedge of different species; the grass weeds are at least one of the following: foxtail grass, barnyard grass, glehnia littoralis, crabgrass, jointed goatgrass, wild oat, wild oat, Japanese wild oat, amaranth, lambsquarters, and reverse-branch amaranth.

9. A pesticide herbicide, composed of an active ingredient and excipients, characterized in that, The active ingredient includes at least one of the compounds described in claim 1 or 2, and the content of the active ingredient is 1 to 99.9999% by weight; preferably, the content of the active ingredient is 1 to 50% by weight.

10. The pesticide herbicide according to claim 9, wherein, The formulation of the pesticide herbicide is selected from one of the following: emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, poison bait, mother liquor, and mother powder.

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