Patent Description:
Chemical weed control with herbicides is the most economical and effective means of weed control. However, long-term and continuous use of single varieties or singles mode of action of chemical herbicides in high doses easily lead to problems such as weed resistance and resistance evolution. Development of new varieties of pesticides is a core means to solve the problems.

Protoporphyrinogen oxidase (PPO, EC <NUM>. <NUM>) can catalyze oxidation of protoporphyrinogen IX into protoporphyrin IX. The PPO is a key enzyme in the same biosynthetic step of chlorophyll and heme. Inhibiting PPO in plants ultimately leads to accumulation and leakage of substrate protoporphyrin IX into cytoplasm, causing lipid peroxidation of the cytoplasm and albinism and death of the plants. In the past few decades, PPO has been widely studied as an important herbicide target.

Studies on uracil compounds as herbicides began in the <NUM> and reached a peak in the <NUM>. In recent years, few varieties have been developed, and patents reported uracil compounds sometimes. For example, CIBA-GEIGY Company disclosed a structure of the following general formula in <CIT>:
<CHM>.

After that, Syngenta successfully developed a commercial herbicide Butafenacil (compound <NUM> in <CIT>), which is mainly used in orchards, including vineyards, cotton fields, and non-cultivated lands to control important gramineous weeds, broad-leaved weeds, sedges, and the like, with good weed control effects.

<CIT> also disclosed preparation of benzoyloxy propionate CK (compound <NUM> in the application) as follows:
<CHM>.

In summary, existing uracil compound herbicides are relatively single in varieties, with little choice. Therefore, novel uracil herbicides with good herbicidal activity are urgently needed in the market.

A technical problem to be solved by the present invention is to provide a novel uracil herbicide with good herbicidal activity.

A technical solution for the present invention to solve the above technical problem is as follows:
A uracil compound containing a carboxylate fragment, a structure of which is shown in the following general formula (I):
<CHM>
in the formula:.

According to a preferred compound of the present invention, in the general formula (I):.

According to a more preferred compound of the present invention, in the general formula (I):.

In definitions of the compounds of the general formula (I) given above, the used terms are generally defined as follows:
Halogen: fluorine, chlorine, bromine, or iodine. Alkyl: linear or branched alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, tertiary or secondary butyl, and isomers. Alkenyl: linear or branched alkenes, such as vinyl, <NUM>-propenyl, <NUM>-propenyl, and different butenyl, pentenyl and hexenyl isomers. The alkenyl further includes polyenes, such as <NUM>,<NUM>-prodienyl and <NUM>,<NUM>-hexadienyl. Alkynyl: linear or branched alkynes, such as ethynyl, propargyl, and different butynyl, pentynyl and hexynyl isomers. The alkynyl further includes polyynes, such as <NUM>,<NUM>-hexanediynyl. Alkoxyalkyl: alkyl-O-alkyl-, such as CH<NUM>OCH<NUM>-. Haloalkoxyalkyl: alkyl-O-alkyl-, on which hydrogen atoms may be partially or completely substituted by halogen atoms, such as ClCH<NUM>OCH<NUM>-. Alkenoxy: alkenyl-O-alkyl-, such as CH<NUM>=CHCH<NUM>OCH<NUM>CH<NUM>-. Haloalkenoxyalkyl: alkenyl-O-alkyl, where O and CH<NUM>=CH are not directly connected, and hydrogen atoms on the alkenyls may be partially or completely substituted by halogen atoms, such as ClCH=CHCH<NUM>OCH<NUM>CH<NUM>-. Alkynoxyalkyl: alkynyl-O-alkyl-, such as CH≡CCH<NUM>OCH<NUM>CH<NUM>-, where O and CH≡C are not directly connected. Haloalkynoxyalkyl: alkynyl-O-alkyl-, where hydrogen atoms on the alkynyls may be substituted by halogen atoms, such as ClC≡CCH<NUM>OCH<NUM>CH<NUM>-. Alkyl S(O)n alkyl: alkyl-S(O)n-alkyl-, n=<NUM>, <NUM> or <NUM>, such as CH<NUM>SCH<NUM>CH<NUM>-, CH<NUM>SOCH<NUM>CH<NUM>-, and CH<NUM>SO<NUM>CH<NUM>CH<NUM>-. Oxygen-containing cycloalkyl: substituted or unsubstituted cyclic oxygen-containing alkyl, such as
<CHM>. Substituent groups include methyl, halogen, cyano, and the like. Oxygen-containing-cycloalkyl-alkyl: substituted or unsubstituted alkyl with cyclic oxygen-containing alkyl, such as
<CHM>
, where substituent groups include methyl, halogen, cyano, and the like.

Some compounds of the present invention may be described by using specific compounds listed in Table <NUM>, but the present invention is not limited to these compounds.

A second aspect of the present invention provides a synthetic method for the foregoing uracil compound containing a carboxylate fragment. Specifically, the method includes a contact reaction between the acid compound shown in formula (II) and a different substituted alcohol, halogenated, or sulfonate compound in the presence of a solvent,
<CHM>
wherein in the general formulas (I) and (II), definitions of R<NUM>, R<NUM>, and R<NUM> are the same as those in claim <NUM>.

The reaction temperature is <NUM>-<NUM>, preferably <NUM>-<NUM>; and the time is <NUM>-<NUM>, preferably <NUM>-<NUM>.

The reaction solvent is selected from at least one of dichloromethane, <NUM>,<NUM>-dichloroethane, tetrahydrofuran, acetonitrile, <NUM>,<NUM>-dioxane, toluene, o-xylene, m-xylene, p-xylene, n-heptane, n-octane, and n-nonane.

In the reaction, a molar ratio of the carboxylic acid compound shown in formula (II) to the different substituted alcohol, halogenated, or sulfonate compound is <NUM>:(<NUM>-<NUM>), preferably <NUM>:(<NUM>-<NUM>).

Some compounds of the general formula (I) of the present invention may be directly obtained through further esterification of the intermediate <NUM>-<NUM>.

Some compounds of the general formula (I) of the present invention may also be esterified directly from the intermediate <NUM>-<NUM> to obtain a carboxylic acid of the general formula (II), or a corresponding ester is hydrolyzed to obtain a carboxylic acid of the general formula (II). The carboxylic acid of the general formula (II) may be further prepared into corresponding acyl chlorides, which are then subjected to contact reactions with different substituted alcohols to obtain some compounds of the general formula (I) of the present invention; the carboxylic acid of the general formula (II) may also be subjected to contact reactions with different substituted alcohols through dehydrating agents to obtain some compounds of the general formula (I) of the present invention; and the carboxylic acid of the general formula (II) may also be subjected to contact reactions with halogenated or sulfonate compounds to obtain some compounds of the general formula (I) of the present invention.

The reaction is carried out in an appropriate solvent, and the appropriate solvent may be selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, <NUM>,<NUM>-dichloroethane, ethyl acetate, or the like. The reaction may be carried out in the presence or absence of an alkali, and when carried out in the presence of an alkali, the reaction may be accelerated. The alkali may be selected from alkali metal hydrides, such as sodium hydride, lithium hydride, or sodium amide; alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide; alkali metal carbonates, such as sodium carbonate or potassium carbonate; and organic alkalies, such as pyridine, <NUM>-dimethylaminopyridine, triethylamine, N-methylpyrrole, or diisopropylethylamine. When a dehydrating agent is used, the dehydrating agent may be <NUM>-ethyl-(<NUM>-dimethylaminopropyl) carbodiimide hydrochloride, N,N-dicyclohexylcarbodiimide, or the like. Acyl chlorides may be prepared by using acylation reagents, such as sulfoxide chloride, oxalyl chloride, and the like. The reaction temperature may range from -<NUM> to a boiling point temperature of the appropriate solvent used in the reaction, generally <NUM>-<NUM>. The reaction time is from <NUM> minutes to <NUM> hours, generally <NUM>-<NUM> hours.

R<NUM>-X or R<NUM>-OH is commercially available. X is a leaving group, and is selected from chlorine, bromine, iodine, or sulfonate.

The foregoing method of the present invention may alternatively include necessary pre-treatment operations on the foregoing raw materials and necessary post-treatment operations on reaction products. The operational means of pre-treatment and post-treatment include, but are not limited to, drying, washing, pulping, filtration, centrifugation, column chromatography, recrystallization, and the like. The example section of the present invention provides several specific treatment means, which should not be understood by those skilled in the art as limiting the present invention.

Unless otherwise noted, the definitions of groups in the reaction formula are the same as before.

A third aspect of the present invention provides a use of the uracil compound containing a carboxylate fragment as a herbicide.

A fourth aspect of the present invention provides a herbicidal composition, including a compound of the general formula (I) as an active ingredient, where a weight percentage content of the active ingredient in the composition is <NUM>-<NUM>%.

The compound of the present invention has outstanding herbicidal activity against broad-spectrum economically important monocotyledonous and dicotyledonous annual harmful plants, may effectively control a variety of weeds, may achieve good results at low doses, and may be used as a herbicide. Therefore, the present invention further includes a use of the compounds of the general formula (I) in control of weeds.

Therefore, the present invention relates to a method for preventing and controlling undesired plants or for regulating plant growth, where one or more compounds of the present invention are applied to plants (for example, harmful plants, such as monocotyledonous or dicotyledonous weeds, or undesired crop plants), seeds (for example, grains, seeds, or asexual propagules, such as tubers or young shoots with buds), or plant growth regions (for example, cultivation regions). The compound of the present invention may be applied before planting (by introduction into soil if appropriate), and before or after seedling. The following examples of various representative monocotyledonous and dicotyledonous weed floras prevented and controlled by the compounds of the present invention are only used to illustrate the present invention, but definitely not limit the present invention.

Genera of monocotyledonous harmful plants include Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum.

Genera of dicotyledonous weeds include Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, and Xanthium.

When the compound of the present invention is applied to soil before seedling, the growth of harmful plant seeds stops after treatment, and harmful plants stay in a growth period at the time of application, or die completely after a period of time, thereby eliminating competition of weeds harmful to crop plants in a lasting manner at an extremely early time point.

When the compound of the present invention is applied to green plant sites after seedling, the growth stops after treatment, and harmful plants stay in a growth period at the time of application, or die completely after a period of time, thereby eliminating competition of weeds harmful to crop plants in a lasting manner at an extremely early time point.

Therefore, the technical solution of the present invention further includes a use of the compounds of the general formula (I) in control of weeds.

In addition, the compounds of the general formula (I) of the present invention are also applicable to drying and/or defoliation of plants.

As mentioned earlier, the present invention provides a pesticide herbicide, which is composed of an active ingredient and excipients, where the active ingredient includes at least one of the foregoing uracil compounds containing a carboxylate fragment.

Preferably, the content of the active ingredient in the pesticide herbicide is <NUM>-<NUM> weight%.

The present invention has no special limitations on specific types of the excipients in the herbicide, such as various surfactants and solvents commonly used in the field of herbicides.

For example, the uracil compound containing a carboxylate fragment described in the present invention may be dissolved and diluted with a solvent for later use, and a concentration after dissolution and dilution with the solvent is preferably <NUM>-<NUM>/L. The solvent for dissolving the uracil compound containing a carboxylate fragment may include at least one of dimethyl sulfoxide and N,N-dimethylformamide, and a reagent for the dilution may be water containing commonly used additives or the like. Preferably, one or more additives commonly used in herbicides in the art, such as surfactants and emulsifiers, may also be added to the solution in which the uracil compound is dissolved.

In order to enhance the prevention and control effect of the uracil compound containing a carboxylate fragment described in the present invention and increase a use scope thereof, the uracil compound containing a carboxylate fragment of the present invention may be used alone or used with other commonly used herbicides (such as atrazine, tetrazolyl oxalamide, bromoxynil, cyclopentaoxone, and nitrosulfazone). In addition, the proportion of combined use is not specially limited and may be a conventional proportion in the art, as long as the prevention and control effect after the combined use can be enhanced, the use scope can be increased and the safety can be improved.

If there is a conflict between the name of a compound in the present invention and the structural formula, the structural formula shall prevail, except that the structural formula is obviously wrong.

The uracil compound containing a carboxylate fragment provided by the present invention has better herbicidal activity compared with the prior art.

The present invention will be described below in conjunction with examples, but is not limited thereto. In the art, any simple replacement or improvement made by a technician to the present invention falls into the technical solution protected by the present invention.

<NUM> of <NUM>-chloro-<NUM>-fluorobenzoic acid and <NUM> of ethanol were put into a <NUM> four-necked flask, stirred, and cooled to <NUM>, and <NUM> of sulfoxide chloride was slowly added dropwise, where the temperature was maintained below <NUM> throughout the process. After the sulfoxide chloride was added, the solution was heated to <NUM> and stirred under reflux and reacted overnight, and the reaction solution was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM> and <NUM> of <NUM>,<NUM>-dichloroethane were added to a <NUM> four-necked flask and cooled to <NUM>, <NUM> of fuming nitric acid (<NUM>%) and <NUM> of sulfuric acid (<NUM>%) were slowly added dropwise, then the solution was slowly heated to room temperature and stirred until the reaction was completed, the reaction solution was transferred to a separating funnel and stood until delamination, an organic phase was taken, an inorganic phase was extracted with <NUM>,<NUM>-dichloroethane, the acid in the organic phase was eluted with ice water until the pH value of the aqueous phase was about <NUM>, and the solvent was spun off to obtain <NUM> of crude product. <NUM> times the mass of n-hexane was added, recrystallization and filtration were carried out, and filter cakes were dried to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of Pt/C (<NUM>%), and <NUM> of ethanol were added into a <NUM> autoclave, hydrogen pressure was controlled to <NUM> MPa, a reaction occurred at <NUM> for <NUM> hours, then the Pt/C was removed by filtration, and the filtrate was spun off to obtain <NUM> of crude intermediate <NUM>-<NUM>.

<NUM> of crude intermediate <NUM>-<NUM>, <NUM> of pyridine, and <NUM> of dichloromethane were added to a <NUM> four-necked flask and stirred at room temperature, and <NUM> of ethyl chloroformate was weighed after <NUM> minutes, diluted with <NUM> of dichloromethane, and then slowly added dropwise within <NUM> hour. After reaction for <NUM> hours, the pH value was adjusted to be weakly acidic, water was added, extraction was carried out with dichloromethane, and the organic phase was spun off to obtain <NUM> of crude intermediate <NUM>-<NUM>.

<NUM> of sodium ethanol was dissolved in <NUM> of DMF, stirred, and cooled to <NUM> in an ice bath. A DMF (<NUM>) solution of ethyl <NUM>-amino-<NUM>,<NUM>,<NUM>-trifluorocrotonate (<NUM>) was added dropwise in the ice bath. Then, a DMF solution of <NUM> of intermediate <NUM>-<NUM> was added dropwise, and the solution was heated to <NUM> and stirred for <NUM>. After the reaction was completed, the pH value was adjusted to be acidic, extraction was carried out with ethyl acetate, the organic phase was washed with saturated salt water and dried with anhydrous sodium sulfate, the solvent was spun off to obtain <NUM> of crude product, and the crude product was purified by column chromatography to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM> and <NUM> of anhydrous potassium carbonate were added to a single-necked flask and dissolved with <NUM> of THF, and <NUM> of dimethyl sulfate was added, followed by stirring overnight at room temperature. After the reaction was completed, the THF was spun off, extraction was carried out with ethyl acetate, the anhydrous sodium sulfate was dried, and the organic phase was spun off to obtain <NUM> of crude intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM> was dissolved in <NUM> of glacial acetic acid at room temperature, the same volume of <NUM>% hydrochloric acid was added, and a reflux reaction occurred for <NUM>. After the reaction was completed, the excess solvent was evaporated under reduced pressure, and water was added to the residue to precipitate solid, followed by stirring and filtration. Filter cakes were washed with water three times, and dried at <NUM> to obtain <NUM> of crude intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of <NUM>,<NUM>-dichloroethane, <NUM> drop of DMF, and <NUM> of dichlorosulfoxide were added to a <NUM> single-necked flask and subjected to a reflux reaction for <NUM>. After the reaction was completed, the excess dichlorosulfoxide and solvent were spun off to obtain <NUM> of crude intermediate <NUM>-<NUM>.

The intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> and <NUM> of methyl glycolate were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of triethylamine was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of hydrochloric acid (<NUM>%), and <NUM> of acetic acid were added to a reaction flask and refluxed for <NUM>, and the reaction solution was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of dichlorosulfoxide, <NUM> drops of DMF, and <NUM> of dichloroethane were added to a reaction flask, a reflux reaction occurred for <NUM>, and the reaction solution was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of <NUM>-methoxyethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) prepared in the last step was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of <NUM>-allyloxyethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of light yellow oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d6) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dq, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of propynol ethoxylate and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of light yellow oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of methyl D-lactate, and <NUM> of dichloromethane were added to a reaction flask, blown with nitrogen, and stirred at room temperature. <NUM> of triethylamine was added dropwise within <NUM>, followed by stirring overnight at room temperature. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of hydrochloric acid (<NUM>%), and <NUM> of acetic acid were added into a reaction flask and stirred at <NUM> for <NUM> until the reaction ended, and the solvent was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>,<NUM> of sulfoxide chloride, <NUM> of <NUM>,<NUM>-dichloroethane, and <NUM> drops of DMF were added into a reaction flask for reflux stirring at <NUM>. After one hour of reaction, the solvent was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of <NUM>-methoxyethanol, <NUM> of dichloromethane, and <NUM> of triethylamine were added to a reaction flask, blown with nitrogen, and stirred at room temperature for <NUM> until the reaction ended. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of <NUM>-allyloxyethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (ddtd, J = <NUM>, <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (qt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dq, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (ddd, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM> was dissolved in <NUM> of <NUM>,<NUM>-dichloroethane, a <NUM>,<NUM>-dichloroethane solution of propynol ethoxylate (<NUM>) was added dropwise, the solution was stirred at <NUM> for <NUM> minutes, and then <NUM> of triethylamine was added dropwise. After the reaction of the raw materials was completed upon LCMS test, <NUM> of hydrochloric acid (1N) was added for washing, the solution was separated, the organic phase was dried with anhydrous sodium sulfate, and column chromatography purification was carried out to obtain <NUM> of colorless oily liquid as compound <NUM>. <NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of <NUM>-(methylthio)ethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of colorless oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of compound <NUM> and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of m-chloroperoxybenzoic acid was added, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of colorless oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of <NUM>-methylsulfonyl ethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J= <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (d, J= <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of dichloromethane, <NUM> of (S)-glycidol, and <NUM> of triethylamine were added to a <NUM> single-necked flask, and stirred overnight at room temperature. After the reaction was completed, <NUM> of water was added, the solution was stirred and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (q, J= <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of dichloromethane, <NUM> of (R)-glycidol, and <NUM> of triethylamine were added to a <NUM> single-necked flask, and stirred overnight at room temperature. After the reaction was completed, <NUM> of water was added, the solution was stirred and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (qd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of methyl L-lactate was added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, and the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, followed by <NUM> of triethylamine. Then, a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of dichlorosulfoxide, <NUM> drops of DMF, and <NUM> of <NUM>,<NUM>-dichloroethane were added to a reaction flask, a reflux reaction occurred for <NUM>, and the reaction solution was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

The intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was weighed into a <NUM> single-necked flask, and <NUM> of dichloromethane, <NUM> of <NUM>-allyloxyethanol, and <NUM> of triethylamine were added, followed by stirring at room temperature for reaction. After <NUM>, the reaction ended upon LCMS test. <NUM> of water was added, and the solution was stirred and separated to obtain an organic phase. The organic phase was dried, and the excess solvent was evaporated under reduced pressure. After column chromatography purification (PE: EA=<NUM>:<NUM>), <NUM> of colorless oily liquid was obtained as compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (ddd, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM> was dissolved in <NUM> of <NUM>,<NUM>-dichloroethane, a <NUM>,<NUM>-dichloroethane solution of propynol ethoxylate (<NUM>) was added dropwise, the solution was stirred at <NUM> for <NUM> minutes, and then <NUM> of triethylamine was added dropwise. After the reaction of the raw materials was completed upon LCMS test, <NUM> of hydrochloric acid (1N) was added for washing, the solution was separated, the organic phase was dried with anhydrous sodium sulfate, and column chromatography purification was carried out to obtain <NUM> of colorless oily liquid as compound <NUM>. <NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of <NUM>-(methylthio)ethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of colorless oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the compound <NUM> described in Example <NUM> and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of m-chloroperoxybenzoic acid was added, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of colorless oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (qt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of <NUM>-methylsulfonyl ethanol and <NUM> of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of dichloromethane, <NUM> of (S)-glycidol, and <NUM> of triethylamine were added to a <NUM> single-necked flask, and stirred overnight at room temperature. After the reaction was completed, <NUM> of water was added, the solution was stirred and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of dichloromethane, <NUM> of (R)-glycidol, and <NUM> of triethylamine were added to a <NUM> single-necked flask, and stirred overnight at room temperature. After the reaction was completed, <NUM> of water was added, the solution was stirred and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (ddd, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J= <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of methyl lactate, and <NUM> of dichloromethane were added to a reaction flask, blown with nitrogen, and stirred at room temperature. <NUM> of triethylamine was added dropwise within <NUM>, followed by stirring overnight at room temperature. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of the intermediate <NUM>-<NUM> described in Example <NUM>, <NUM> of <NUM>-methoxyethanol, <NUM> of dichloromethane, and <NUM> of triethylamine were added to a reaction flask, blown with nitrogen, and stirred at room temperature for <NUM> until the reaction ended. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s,, <NUM>), <NUM> (d, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

With reference to the methods of Examples <NUM> and <NUM>, compound <NUM> was prepared by using the intermediate <NUM>-<NUM> described in Example <NUM> and <NUM>-allyloxyethanol.

With reference to the methods of Examples <NUM> and <NUM>, compound <NUM> was prepared by using the intermediate <NUM>-<NUM> described in Example <NUM> and propynol ethoxylate. <NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of compound <NUM> and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of m-chloroperoxybenzoic acid was added, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of colorless oil as compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (qt, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (d, J= <NUM> Hz, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

With reference to the methods of Examples <NUM> and <NUM>, compound <NUM> was prepared by using the intermediate <NUM>-<NUM> described in Example <NUM> and (S)-glycidol. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

With reference to the methods of Examples <NUM> and <NUM>, compound <NUM> was prepared by using the intermediate <NUM>-<NUM> described in Example <NUM> and (R)-glycidol. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (qd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J= <NUM>, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of methyl <NUM>-hydroxyisobutyrate, <NUM> of DMAP, and <NUM> of dichloromethane were added to a reaction flask, blown with nitrogen, and stirred at room temperature. <NUM> of the intermediate <NUM>-<NUM> described in Example <NUM> was added dropwise within <NUM>, followed by stirring at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of hydrochloric acid (<NUM>%), and <NUM> of acetic acid were added into a reaction flask and stirred at <NUM> for <NUM>. After a reaction ended, the reaction solution was poured into <NUM> of ice water, extraction was carried out with EA, and the organic phase was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of <NUM>-methoxyethanol, <NUM> of dichloromethane, and <NUM> of triethylamine were added into a reaction flask, blown with nitrogen, and stirred at room temperature. After the reaction was completed, <NUM> of water was added, and the solution was stirred and separated to obtain an organic phase. The organic phase was dried, and the excess solvent was evaporated under reduced pressure. Column chromatography purification was carried out to obtain <NUM> of white solid as compound <NUM>. <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>). LCMS (ESI) [M + H]+ = <NUM>, Found =<NUM>.

<NUM> of <NUM>-allyloxyethanol, <NUM> of DMAP, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (dt, J= <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (s, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of (S)-glycidol, <NUM> of DMAP, <NUM> of triethylamine, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, and blown with nitrogen. <NUM> of the intermediate <NUM>-<NUM> described in Example <NUM> was added dropwise to dissolve in <NUM> of dichloromethane solution, and a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of oily compound as compound <NUM>. <NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dq, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of (R)-glycidol, <NUM> of DMAP, <NUM> of triethylamine, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, and blown with nitrogen. <NUM> of dichloromethane solution of <NUM> of the intermediate <NUM>-<NUM> described in Example <NUM> was added dropwise, and a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of oily compound as compound <NUM>. <NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dq, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

With reference to the methods of Examples <NUM> and <NUM>, compound <NUM> was prepared by using the intermediate <NUM>-<NUM> described in Example <NUM> and glycidol. <NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (d, J= <NUM>, <NUM>), <NUM> (d, J= <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J= <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dq, J = <NUM>, <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (s, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of methyl <NUM>-hydroxy-<NUM>-cyclopropanecarboxylate, <NUM> of DMAP, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of intermediate <NUM>-<NUM>, <NUM> of sulfoxide chloride, <NUM> of <NUM>,<NUM>-dichloroethane, and <NUM> drops of DMF were added into a reaction flask for reflux stirring at <NUM>. After one hour of reaction, the solvent was spun off to obtain <NUM> of intermediate <NUM>-<NUM>.

<NUM> of <NUM>-methoxyethanol, <NUM> of triethylamine, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (s, <NUM>), <NUM>-<NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of (S)-glycidol, <NUM> of triethylamine, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) described in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (ddt, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

<NUM> of (R)-glycidol, <NUM> of triethylamine, and <NUM> of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen, <NUM> of dichloromethane solution of the intermediate <NUM>-<NUM> (<NUM>) descried in Example <NUM> was added dropwise, and then a reaction occurred at room temperature for <NUM>. After the reaction was completed, column chromatography purification was carried out to obtain <NUM> of compound <NUM>. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (ddt, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

With reference to the methods of Examples <NUM> and <NUM>, compound <NUM> was prepared by using the intermediate <NUM>-<NUM> described in Example <NUM> and glycidol. <NUM>H NMR (<NUM>, DMSO-d<NUM>) δ <NUM> (d, J = <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>), <NUM> (s, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (ddt, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> (dd, J = <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>). LCMS (ESI) [M + H]+ =<NUM>, Found =<NUM>.

A herbicidal activity test method for the compounds of the present invention was as follows:
Seed Treatment; pre-emergence: quantitative seeds of gramineous weeds (Echinochloa crusgalli, Eleusine indica, Digitaria sanguinalis, Alopecurus japonicus, Beckmannia syzigachne, Leptochloa chinensis, Polypogon fugax, Alopecurus aequalis, Lolium multiflorum, and Poa annua), broad-leaved weeds (Eclipta prostrata, Amaranthus retroflexus, Brassica juncea, Malachium aquaticum, Conyza canadensis, and Sesbania cannabina), and Cyperus iria were sown in plastic pots having a diameter of <NUM> and holes at the bottom and filled with nutrient soil (sandy soil, pH <NUM>, organic matter <NUM>%) respectively, the seeds were covered with an appropriate amount of soil after being sown, then the soil was wetted with water from the bottom, the seeds were cultured in a constant-temperature illuminated culture room for <NUM>, and the soil was sprayed by using a 3WP-<NUM> traveling spray tower produced by the Nanjing Institute of Agricultural Mechanization of the Ministry of Agriculture, where a rotational speed of a main shaft was <NUM>/r, a spray height was <NUM>, an effective spraying range of a nozzle was <NUM>, a spray area was <NUM><NUM>, and a flow rate at the nozzle was <NUM>/min.

Post-emergence: an appropriate quantity of seeds of gramineous weeds (Echinochloa crusgalli, Eleusine indica, Digitaria sanguinalis, Alopecurus japonicus, Beckmannia syzigachne, Leptochloa chinensis, Polypogon fugax, Alopecurus aequalis, Lolium multiflorum, and Poa annua), broad-leaved weeds (Eclipta prostrata, Amaranthus retroflexus, Brassica juncea, Malachium aquaticum, Conyza canadensis, and Sesbania cannabina), and Cyperus iria were sown in plastic pots having a diameter of <NUM> and holes at the bottom and filled with nutrient soil (sandy soil, pH <NUM>, organic matter <NUM>%) respectively, the seeds were covered with an appropriate amount of soil after being sown, then the soil was wetted with water from the bottom, the seeds were cultured in a constant-temperature illuminated culture room until a <NUM>-<NUM> leaf stage, and stems and leaves underwent spray treatment. After the treatment, the test materials were placed in a laboratory and cultured in the constant-temperature illuminated culture room after the liquid was naturally dry in the shade, and results were determined <NUM> days later.

Classification standards for prevention and control effects:.

The test results showed that the compounds of the general formula (I) generally had excellent prevention and control effects on various weeds at a dose of <NUM> a. /hm<NUM>, reaching class A.

According to the foregoing test method, a parallel experiment was carried out on herbicidal activities of some compounds of the general formula (I), the compound Butafenacil (compound <NUM> in the patent specification) specifically disclosed in <CIT>, and the compound CK (compound <NUM> in the patent specification) specifically disclosed in <CIT>, at application doses of <NUM> a. /ha and <NUM> a. Results were shown in Table <NUM>:.

Claim 1:
A uracil compound containing a carboxylate fragment, a structure of which is shown in the following general formula (I):
<CHM>
in the formula:
R<NUM> and R<NUM> are selected from hydrogen or methyl respectively; or R<NUM> and R<NUM> together with the carbon atom they are attached form a <NUM>-membered carbocycle;
R<NUM> is selected from C<NUM>-<NUM> alkoxy C<NUM>-<NUM> alkyl, C<NUM>-<NUM> haloalkoxy C<NUM>-<NUM> alkyl, C<NUM>-<NUM> alkenoxy C<NUM>-<NUM> alkyl, C<NUM>-<NUM> haloalkenoxy C<NUM>-<NUM> alkyl, C<NUM>-<NUM> alkynoxy C<NUM>-<NUM> alkyl, C<NUM>-<NUM> haloalkynoxy C<NUM>-<NUM> alkyl, C<NUM>-<NUM> alkyl S(O)n C<NUM>-<NUM> alkyl, C<NUM>-<NUM> oxygen-containing cycloalkyl C<NUM>-<NUM> alkyl, or C<NUM>-<NUM> oxygen-containing cycloalkyl;
n=<NUM>, <NUM>, or <NUM>; and
when R<NUM> is selected from hydrogen and R<NUM> is selected from methyl, the chiral carbon atom connected thereto may be selected from either an R configuration or an S configuration, or a mixture of the two; and in the mixture, a ratio of R to S is <NUM>:<NUM> to <NUM>:<NUM>.