Uracil compound containing a carboxylate fragment, method for preparing such compound, use of the compound and composition comprising the same.

Description

Uracil compound containing a carboxylate fragment, method for preparing such compound, use of the compound and composition comprising the same. TECHNICAL AREA

[001] The present invention relates to the field of herbicidal pesticides and, in particular, to a uracil compound containing a carboxylate fragment, a method of preparing this compound and a herbicidal composition and its use. CONTEXT

[002] Chemical weed control with herbicides is the most economical and effective means of weed control. However, prolonged and continuous use of a single variety or mode of action of chemical herbicides at high doses easily leads to problems such as weed resistance and the evolution of resistance. The development of new varieties of pesticides is a fundamental means of solving these problems.

[003] Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) can catalyze the oxidation of protoporphyrinogen IX to protoporphyrin IX. PPO is a key enzyme in the same biosynthetic step as chlorophyll and heme. Inhibition of PPO in plants leads to the accumulation and leakage of the substrate protoporphyrin IX into the cytoplasm, causing cytoplasmic lipid peroxidation and albinism and plant death. In recent decades, PPO has been extensively studied as an important herbicide target.

[004] Studies on uracil compounds as herbicides began in the 1960s and peaked in the 1990s. In recent years, few varieties have been developed, and uracil compounds have occasionally appeared in patents. For example, CIBA-GEIGY disclosed a structure of the following general formula in US5183492A: Petition 870230062726, dated 07 / 18 / 2023, page 9 / 159 2 / 63

[005] After that, Syngenta successfully developed a commercial herbicide Butafenacil (compound 47 in US5183492A), which is used primarily in orchards, including vineyards, cotton fields and uncultivated land in order to control important grassy weeds, broadleaf weeds, sedges and the like, with good weed control effects. Butafenacil

[006] US5183492A also disclosed the preparation of benzoyloxy CK propionate (compound 1 in the application) as follows: CK

[007] In summary, existing uracil-based herbicides are relatively unique in variety, with few options. Therefore, it is urgent that new uracil herbicides with good herbicidal activity reach the market. BRIEF DESCRIPTION OF THE INVENTION

[008] A technical problem to be solved by the present invention is the provision of a new uracil herbicide. Petition 870230062726, dated 07 / 18 / 2023, p. 10 / 159 3 / 63 with good herbicidal activity.

[009] A technical solution for the present invention to solve the above technical problem is as follows:

[010] A uracil compound containing a carboxylate fragment, whose structure is shown in the following general formula (I): in the formula: R1 and R2 are selected from hydrogen or methyl, respectively; or R1 and R2 together with the carbon atom to which they are attached form a 3-membered carbocycle; R3 is selected from C1-3 alkoxy, C1-3 alkyl, C1-3 haloalkoxy, C1-3 alkyl, C2-6 alkenoxy, C1-3 alkyl, C2-6 haloalkenoxy, C1-3 alkyl, C2-6 alkynoxy, C1-3 alkyl, C2-6 haloalkynoxy, C1-3 alkyl, C1-3 alkyl, S(O)n, C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl; n=0, 1 or 2; and when Ri is selected from hydrogen, and R2 is selected from methyl, the chiral carbon atom connected to it can be selected from an R configuration or an S configuration, or a mixture of the two.

[011] According to a preferred compound of the present invention, in general formula (I): R1 and R2 are selected from hydrogen or methyl, respectively; or R1 and R2 together with the carbon atom to which they are attached form a 3-membered carbocycle; R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 Petition 870230062726, dated 07 / 18 / 2023, page 11 / 159 4 / 63 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkynexy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl; and when R1 is selected from hydrogen and R2 is selected from methyl, the chiral carbon atom connected to it may be selected from an R configuration or an S configuration, or a mixture of the two; and, in the mixture, the ratio of R to S is 1:99 to 99:1.

[012] According to a more preferred compound of the present invention, in general formula (I): R1 and R2 are selected from hydrogen or methyl, respectively; R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkynexy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl; and when Ri is selected from hydrogen and R2 is selected from methyl, the chiral carbon atom connected to it may be selected from an R configuration or an S configuration, or a mixture of the two; and, in the mixture, the ratio of R to S is 1:99 to 99:1.

[013] In the definitions of compounds of general formula (I) given above, the terms used 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, 1-propenyl, Petition 870230062726, dated 07 / 18 / 2023, p. 12 / 159 5 / 63 2-propenyl and different isomers of butenyl, pentenyl, and hexenyl. Alkenyl also includes polyenes, such as 1,2-prodienyl and 2,4-hexadienyl. Alkynyl: linear or branched alkynes, such as ethynyl, propargyl, and different isomers of butynyl, pentynyl, and hexynyl. Alkynyl also includes polyynes, such as 2,4-hexanediinyl. Alkoxyalkyl: alkyl-O-alkyl-, such as CH3OCH2-. Haloalkoxyalkyl: alkyl-O-alkyl-, in which the hydrogen atoms may be partially or totally replaced by halogen atoms, such as CICH2OCH2-. Alcenoxy: alkenyl-O-alkyl-, such as CH2=CHCH2OCH2CH2-. Haloalkenoxyalkyl: alkenyl-O-alkyl, where O and CH2=CH are not directly bonded, and the hydrogen atoms in the alkenes may be partially or totally replaced by halogen atoms, such as C1CH=CHCH2OCH2CH2-. Alkynoxyalkyl: alkynyl-O-alkyl-, such as CH=CCH2OCH2CH2-, where O and CH=C are not directly bonded.Haloalkynoxyalkyl: alkynyl-O-alkyl-, in which the hydrogen atoms in the alkynes can be replaced by halogen atoms, such as C1C^CCH2OCH2CH2-. Alkyl S(O)nalkyl: alkyl-S(O)n-alkyl-, n=0, 1 or 2, such as CH3SCH2CH2-, CH3SOCH2CH2-, and CH3SO2CH2CH2-. Cycloalkyl containing oxygen: cyclic alkyl containing substituted or unsubstituted oxygen, such as '. Substituent groups include methyl, halogen, cyano, and the like. Oxygen-containing cycloalkyl: alkyl substituted or unsubstituted by cyclic oxygen-containing alkyl, such as θ, wherein the substituent groups include methyl, halogen, cyano, and the like.

[014] Some compounds of the present invention can be described using specific compounds listed in Table 1, but the present invention is not limited to those compounds. Petition 870230062726, dated 07 / 18 / 2023, page 13 / 159 6 / 63 Table 1 Compound number Ri r2 r3 State Melting point 1 HH 2 HH 3 HH Colorless oil - 4 HH 5 HH 6 HH 7 HH 8 HH y Br 9 HH 10 HH Light yellow oil - 11 HH 12 HH 13 HH 14 HH Cl 15 HH Cl 16 HH 17 HH Br 18 HH y^^o-^ 19 HH 20 HH Petition 870230062726, dated 07 / 18 / 2023, page 14 / 159 7 / 63 Compound Number Ri R2 r3 State Melting Point 21 HH 22 HH 23 HH Cl 24 HH Cl 25 HH 26 HH Br 27 HH 28 HH Light Yellow Oil - 29 HH 30 HH 36 HH ^Br 37 HHY^ / S\ 38 HH 39 HH 40 HH γχ\χ^5'χ^' Petition 870230062726, dated 07 / 18 / 2023, page 15 / 159 8 / 63 Compound Number Ri r2 r3 State Melting Point 41 HH 0 42 HH 1 CO O / M 43 HHO 44 HHO CO 45 HH 46 HH 47 HH o 48 HH 49 HH 50 HH 51 HH 52 H Aoh3 53 H Aoh3 54 H Aoh3 Colorless Oil - 55 H Aoh3 56 H Adh3 57 H Adh3 58 H Aoh3 59 H Aoh3 60 H Aoh3 Petition 870230062726, dated 07 / 18 / 2023, p. 16 / 159 9 / 63 Compound number Ri R2 r3 State Melting point 61 H ^ch3 Colorless oil - 62 H Aoh3 63 H Aoh3 64 H Aoh3 65 H ^ch3 Cl 66 H Adh3 Cl 67 H Aoh3 68 H ^ch3 Br 69 H Aoh3 70 HA?h3 71 HA?h3 72 H Adh3 73 HA?h3 74 H Aoh3 Cl 75 H Adh3 Cl Y'''^'O^· 76 H Aoh3 77 H Adh3 Br γ^^Ο'χ^<ί^ 78 H ^ch3 γ^ / Ο\^ 79 H Aoh3 Colorless oil - 80 H Aoh3 Petition 870230062726, dated 07 / 18 / 2023, p. 17 / 159 10 / 63 Compound Number Ri r2 r3 State Melting Point 81 H A)H3 ,CI 82 H ^ch3 Br 83 HA?h3 84 H Adh3 85 H ^ch3 86 H Aoh3 87 H ^ch3 ^Br 88 H ^ch3 Colorless oil - 89 H Aoh3 90 H Aoh3 91 H Adh3 92 H Aoh3 0 Y^ / S\ Colorless oil - 93 H ^ch3 CM / O ω Colorless oil - 94 HA?h3 0 95 H ^ch3 1 ω ο c 96 H ^ch3 Colorless oil - 97 H Aoh3 Colorless oil - 98 H Aoh3 99 H Aoh3 Petition 870230062726, dated 07 / 18 / 2023, p. 18 / 159 11 / 63 Compound number Ri r2 r3 State Melting point 100 H ^ch3 v^° 101 H Aoh3 102 HA?h3 vO 103 H ^Z / ch3 104 H / 'ζΟΗ3 105 H / 'όη3 Colorless oil - 106 H ^Z / ch3 107 H ^ch3 108 H / 'όη3 109 H ^Z / ch3 110 H ^ch3 \ .-0 Br 111 H / 'όη3 112 H ^Z / ch3 Colorless oil - 113 H ^ch3 114 H ^Z / ch3 115 H ^Z / ch3 116 H / 'όη3 Cl 117 H ^Z / ch3 Cl 118 H ^Z / ch3 119 H / 'zCH3 Br Petition 870230062726, dated 07 / 18 / 2023, page 19 / 159 12 / 63 Compound number Ri R2 r3 State Melting point 120 H ^Z / ch3 121 H / 'ζΟΗ3 122 HA;h3 123 H / 'ζΟΗ3 124 H / 'zCH3 125 H / 'zCH3 Cl 126 H ^'zch3 Cl 127 H ^'zch3 128 H / 'zCH3 Br 129 H / 'zCH3 γ~\^°'\^ 130 H ^'zch3 γ^χ / ο\χ>^ Colorless oil - 131 H / 'zCH3 132 H ^'zch3 ,d 133 H / 'zCH3 Br 134 H / 'zCH3 135 H / 'zCH3 136 H / 'zCH3 137H / 'zCH3 X)l 138 H ^'zch3 ^Br Petition 870230062726, dated 07 / 18 / 2023, page 20 / 159 13 / 63 Compound Number Ri r2 R3 State Melting Point 139 H ^Z / ch3 Colorless oil - 140 H / 'ζOH3 141 H;h3 142 H ^Z / ch3 143 H ^ch3 0 Colorless oil - 144 H / ch3 CM / O CO i Colorless oil - 145 H;h3 0 146 H ^ch3 1 ω oc 147 H ^ch3 Colorless oil - 148 H ^ch3 Colorless oil - 149 H ^Z / ch3 150 H ^Z / ch3 151 H ^ch3 152 H;h3 153 H ^ch3 vO 154 ch3 H 155 ch3 H 156 ch3 H Colorless oil - 157 ch3 H 158 ch3 H XX~X-^'O / Petition 870230062726, dated 07 / 18 / 2023, page 21 / 159 14 / 63 Compound number Ri r2 r3 State Melting point 159 CH3 H 160 CH3 H 161 CH3 HY^-^Br 162 CH3 H 163 CH3 H γ^ο^^ Colorless oil - 164 CH3 H 165 CH3 H 166 CH3 H 167 CH3 H γ^^°-^γ Cl 168 CH3 H γ-^^Q^ / c^ Cl 169 CH3 H Yx\^°\ / ^'Br 170 CH3 H Br 171 CH3 HY^-^o^ 172 CH3 H 173 CH3 H 174 CH3 H 175 CH3 H 176 CH3 H Cl 177 CH3 H Cl 178 CH3 H 179 ch3 H Br 180 ch3 H Petition 870230062726, dated 07 / 18 / 2023, page 22 / 159 15 / 63 Compound number Ri R2 r3 State Melting point 181 CH3 H Colorless oil - 182 CH3 H 183 CH3 HQ, 184 CH3 H 185 CH3 H 186 CH3 H 187 CH3 H 188 CH3 HY^^^o·'''^^ 189 CH3 H ^^^Br 190 CH3 H Colorless oil - 191 CH3 H 192 CH3 HY^^^s^ 193 CH3 H 194 CH3 H 0 Y^ / S\ Colorless oil - 195 CH3 H CM / O CO / Colorless oil - 196 CH3 H 0 197 CH3 H 1 ω oc 198 CH3 H Colorless oil - 199 CH3 H Colorless oil - 200 CH3 H Petition 870230062726, dated 07 / 18 / 2023, page 23 / 159 16 / 63 Compound number Ri r2 r3 State Melting point 201 ch3 H 202 ch3 H 203 ch3 H 204 ch3 H vO 205 ch3 ch3 y^o^ 206 ch3 ch3 y^o·^^' 207 ch3 ch3 White solid 71.5 to 7 9.7°C 208 ch3 ch3 209 ch3 ch3 y^-^o^ 210 ch3 ch3 211 ch3 ch3 Y^°-^ci 212 ch3 ch3 y^-^Br 213 ch3 ch3 214 ch3 ch3 Colorless oil - 215 ch3 ch3 216 ch3 ch3 217 ch3 ch3 218 ch3 ch3 Cl 219 ch3 ch3 Cl 220 ch3 ch3 221 ch3 ch3 Br 222 ch3 ch3 Petition 870230062726, dated 07 / 18 / 2023, page 24 / 159 17 / 63 Compound number Ri r2 r3 State Melting point 223 ch3 ch3 224 ch3 ch3 225 ch3 ch3 226 ch3 ch3 227 ch3 ch3 Cl 228 ch3 ch3 Cl 229 ch3 ch3 230 ch3 ch3 Br 231 ch3 ch3 232 ch3 ch3 233 ch3 ch3 234 ch3 ch3 ,CI 235 ch3 ch3 236 ch3 ch3 237 ch3 ch3 238 ch3 ch3 239 ch3 ch3 X / ''^''^O''''^ X3I 240 ch3 ch3 χ^'^^O·'''^^ ^Br 241 ch3 ch3 242 ch3 ch3 243 ch3 ch3 XT^^s^ Petition 870230062726, dated 07 / 18 / 2023, page 25 / 159 18 / 63 Compound Number Ri R2 r3 State Melting Point 244 ch3 ch3 Yx / x's / x 245 ch3 ch3 0 246 ch3 ch3 CM / O ω 247 ch3 ch3 o 248 ch3 ch3 O CO 1 249 ch3 ch3 Colorless oil - 250 ch3 ch3 4 Colorless oil - 251 ch3 ch3 Colorless oil - 252 ch3 ch3 253 ch3 ch3 254 ch3 ch3 255 ch3 ch3 256 -CH2CH2- 257 -CH2CH2- 258 -CH2CH2- Colorless oil - 259 -CH2CH2- 260 -CH2CH2- 261 -CH2CH2- 262 -CH2CH2- Y'-°-ci 263 -CH2CH2- 264 -CH2CH2- Petition 870230062726, dated 07 / 18 / 2023, page 26 / 159 19 / 63 Compound number Ri Rz r3 State Melting point 265 -CH2CH2- 266 -CH2CH2- 267 -CH2CH2- \ / \ / °\ / ^ 268 -CH2CH2- 269 -CH2CH2- Cl 270 -CH2CH2- Cl 271 -CH2CH2- 272 -CH2CH2- Br 273 -CH2CH2- 274 -CH2CH2- 275 -CH2CH2- 276 -CH2CH2- 277 -CH2CH2- 278 -CH2CH2- Cl 279 -CH2CH2- Cl 280 -CH2CH2- Br 281 -CH2CH2- Br 282 -CH2CH2- 283 -CH2CH2- 284 -CH2CH2- 285 -CH2CH2- ,Ci Petition 870230062726, dated 07 / 18 / 2023, page 27 / 159 20 / 63 Compound Number Ri R2 R3 State Melting Point 286 -CH2CH2- Br 287 -CH2CH2- 288 -CH2CH2- 289 -CH2CH2- 290 -CH2CH2- 291 -CH2CH2- ^Br 292 -CH2CH2- 293 -CH2CH2- 294 -CH2CH2- Y^-^s^ 295 -CH2CH2- Yx\^'S' / ^ 296 -CH2CH2- 0 297 -CH2CH2- CM / O CO / 298 -CH2CH2- 0 299 -CH2CH2- O CO / 300 -CH2CH2- Colorless oil - 301 -CH2CH2- Colorless oil - 302 -CH2CH2- 0 Colorless oil - 303 -CH2CH2- 304 -CH2CH2- 305 -CH2CH2- Y^^0 Petition 870230062726, dated 07 / 18 / 2023, page 28 / 159 21 / 63 Compound number Ri R2 R3 State Melting point 306 -CH2CH2-

[015] A second aspect of the present invention provides a synthetic method for the above uracil compound containing a carboxylate fragment. Specifically, the method includes a contact reaction between the acidic compound shown in formula (II) and a compound other than substituted alcohol, halogenated or sulfonate in the presence of a solvent, (II) (I) wherein in the general formulas (I) and (II), the definitions of Ri, R2 and R3 are the same as in claim 1.

[016] The reaction temperature is 0 to 160°C, preferably 20 to 120°C; and the time is 2 to 15 hours, preferably 3 to 12 hours.

[017] The reaction solvent is selected from at least one of dichloromethane, 1,2-dichloroethane, tetrahydrofuran, acetonitrile, 1,4-dioxane, toluene, o-xylene, m-xylene, p-xylene, n-heptane, n-octane and n-nonane.

[018] In the reaction, a molar ratio of the carboxylic acid compound shown in formula (II) to the different substituted, halogenated or sulfonate alcohol compound is 1:(1-4), preferably 1:(1,1-3).

[019] Some compounds of general formula (I) of the present invention can be obtained directly by further esterification of intermediate 1-8. Petition 870230062726, dated 07 / 18 / 2023, page 29 / 159 22 / 63 Intermediate 1-8

[020] Some compounds of general formula (I) of the present invention can also be esterified directly from intermediate 1-8 to obtain a carboxylic acid of general formula (II), or a corresponding ester is hydrolyzed to obtain a carboxylic acid of general formula (II). The carboxylic acid of general formula (II) can also be prepared in corresponding acyl chlorides, which are then subjected to contact reactions with different substituted alcohols to obtain some compounds of general formula (I) of the present invention; the carboxylic acid of general formula (II) can also be subjected to contact reactions with different substituted alcohols via dehydrating agents to obtain some compounds of general formula (I) of the present invention; and the carboxylic acid of general formula (II) can also be subjected to contact reactions with halogenated or sulfonate compounds to obtain some compounds of general formula (I) of the present invention. Petition 870230062726, dated 07 / 18 / 2023, p. 30 / 159 23 / 63

[021] The reaction is carried out in a suitable solvent, and the suitable solvent may be selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, 1,2-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 alkalis, such as pyridine, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole or diisopropylethylamine. When a dehydrating agent is used, the dehydrating agent may be 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, N,N-dicyclohexylcarbodiimide or similar. Acyl chlorides can be prepared using acylation reagents such as chloride sulfoxide, oxalyl chloride and similar. The reaction temperature can vary from -10°C to the boiling point temperature of Petition 870230062726, dated 07 / 18 / 2023, page 31 / 159 24 / 63 suitable solvent used in the reaction, generally from 0 to 100°C. The reaction time is 30 minutes to 20 hours, generally 1 to 10 hours.

[022] R3-X or R3-OH is commercially available. X is a labile group, and is selected from chlorine, bromine, iodine or sulfonate.

[023] The above method of the present invention may alternatively include pretreatment operations required on the above raw materials and posttreatment operations required on the reaction products. The operational means of pretreatment and posttreatment 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.

[024] Unless otherwise indicated, the definitions of groups in the reaction formula are the same as before.

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

[026] A fourth aspect of the present invention provides a herbicidal composition, including a compound of general formula (I) as an active ingredient, wherein a percent weight content of the active ingredient in the composition is from 0.1% to 99.9%.

[027] The compound of the present invention has excellent broad-spectrum herbicidal activity against economically important annual monocotyledonous and dicotyledonous weeds, can effectively control a variety of weeds, can achieve good results at low doses, and can be used as a herbicide. Therefore, the present invention includes Petition 870230062726, dated 07 / 18 / 2023, page 32 / 159 25 / 63 still the use of compounds of general formula (I) in weed control.

[028] Therefore, the present invention relates to a method for preventing and controlling unwanted plants or for regulating plant growth, wherein one or more compounds of the present invention are applied to plants (for example, noxious plants such as monocotyledonous or dicotyledonous weeds, or unwanted crop plants), seeds (for example, grains, seeds or asexual propagules such as tubers or young shoots with buds) or plant growth regions (for example, crop regions). The compound of the present invention can be applied before planting (by introduction into the soil, if suitable) 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 used only to illustrate the present invention, but definitely do not limit the present invention.

[029] Genera of monocotyledonous noxious 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.

[030] Dicotyledonous weed genera 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, Petition 870230062726, dated 18 / 07 / 2023, p. 33 / 159 26 / 63 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.

[031] When the compound of the present invention is applied to the soil before seedling, the growth of noxious plant seeds stops after treatment, and the noxious plants remain in a growth period at the time of application or die completely after a period of time, thus eliminating harmful weed competition to cultivated plants in a lasting way at an extremely early point in time.

[032] When the compound of the present invention is applied to green plant sites after seedling, growth stops after treatment, and noxious plants remain in a growth period at the time of application or die completely after a period of time, thus eliminating harmful weed competition to cultivated plants in a lasting way at an extremely early temporal point.

[033] Therefore, the technical solution of the present invention also includes the use of the compounds of general formula (I) in weed control.

[034] Furthermore, the compounds of general formula (I) of the present invention are also applicable to the drying and / or defoliation of plants.

[035] As mentioned previously, the present invention provides a pesticide herbicide, which is composed of an active ingredient and excipients, wherein the active ingredient includes Petition 870230062726, dated 07 / 18 / 2023, page 34 / 159 27 / 63 at least one of the above uracil compounds containing a carboxylate fragment.

[036] Preferably, the active ingredient content in the pesticide herbicide is from 0.1% to 99.9% by weight.

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

[038] For example, the uracil compound containing a carboxylate fragment described in the present invention can be dissolved and diluted with a solvent for subsequent use, and a concentration after dissolution and dilution with the solvent is preferably 0.05 to 0.4 g / 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 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.

[039] In order to increase the prevention and control effect of the uracil compound containing a carboxylate fragment described in the present invention and to increase its scope of use, the uracil compound containing a carboxylate fragment of the present invention can be used alone or with other commonly used herbicides (such as atrazine, tetrazolyl oxalamide, bromoxynil, cyclopentaxone and nitrosulfazone). Furthermore, the ratio of combined use is not especially limited and can be a conventional ratio in the art, provided that the effect of Petition 870230062726, dated 07 / 18 / 2023, page 35 / 159 28 / 63 prevention and control after combined use can be improved, the scope of use can be increased and safety enhanced.

[040] 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 if the structural formula is obviously wrong.

[041] The uracil compound containing a carboxylate fragment provided by the present invention has better herbicidal activity compared with the prior art. DETAILED DESCRIPTION OF THE MODALITIES

[042] The present invention will be described below with examples, but is not limited to them. In the art, any simple substitution or improvement made by a technician to the present invention falls within the technical solution protected by the present invention. Example 1: Intermediate Preparation 1-8 Step 1: Intermediate preparation 1-on-1 THE

[043] 20 g of 2-chloro-4-fluorobenzoic acid and 100 g of ethanol were placed in a 500 ml four-necked flask, stirred and cooled to 0°C, and 17.73 g of chloride sulfoxide were added slowly, dropwise, while the temperature was maintained below 0°C throughout the process. After the chloride sulfoxide was added, the solution was heated to 75°C and stirred under reflux and reacted overnight, and the reaction solution was centrifuged to obtain 23.01 g of intermediate 1-1. Step 2: Intermediate preparation 1-2 Petition 870230062726, dated 07 / 18 / 2023, page 36 / 159 29 / 63 O

[044] 67.46 g of intermediate 1-1 and 337.3 g of 1,2-dichloroethane were added to a 1 L four-necked flask and cooled to 0°C, 42.09 g of fuming nitric acid (90%) were added, and 60.12 g of sulfuric acid (98%) were added slowly, dropwise, then the solution was slowly heated to room temperature and stirred until the reaction was complete, the reaction solution was transferred to a separatory funnel and left until delamination, an organic phase was removed, an inorganic phase was extracted with 1,2-dichloroethane, the acid in the organic phase was eluted with ice-cold water until the pH of the aqueous phase was about 7.0, and the solvent was centrifuged to obtain 89.81 g of crude product. Five times the mass of n-hexane was added, recrystallization and filtration were performed, and the filter cakes were dried to obtain 42.45 g of intermediate 1-2. Step 3: Intermediate preparation 1-3 THE

[045] 60.84 g of intermediate 1-2, 4.87 g of Pt / C (5%) and 300 ml of ethanol were added to a 1 L autoclave, the hydrogen pressure was controlled to 2 MPa, a reaction was carried out at 45°C for 11 hours, then the Pt / C was removed by filtration, and the filtrate was centrifuged to obtain 52.48 g of crude intermediate 1-3. Step 4: Intermediate preparation 1-4 Petition 870230062726, dated 07 / 18 / 2023, page 37 / 159 30 / 63

[046] 52.48 g of crude intermediate 1-3, 24.78 g of pyridine and 262.4 g of dichloromethane were added to a 500 ml four-necked flask and shaken at room temperature, and 34.02 g of ethyl chloroformate were weighed after 5 minutes, diluted with 68.04 g of dichloromethane and then slowly added dropwise over 1 hour. After a reaction for 5 hours, the pH was adjusted to be slightly acidic, water was added, extraction was carried out with dichloromethane and the organic phase was centrifuged to obtain 69.62 g of crude intermediate 1-4. Step 5: Intermediate preparation 1-5

[047] 12.98 g of sodium ethanol were dissolved in 38 g of DMF, stirred, and cooled to 5°C in an ice bath. A solution of DMF (28 g) of ethyl 3-amino-4,4,4-trifluorocrotonate (27.95 g) was added dropwise to the ice bath. Then, a solution of DMF from 36.84 g of intermediate 1-4 was added dropwise, and the solution was heated to 100°C and stirred for 5 hours. After the reaction was complete, the pH was adjusted to acidity, extraction was performed with ethyl acetate, the organic phase was washed with saturated salt water and dried with anhydrous sodium sulfate, the solvent was centrifuged to obtain 50 g of crude product, and the crude product was purified by column chromatography to obtain 19.05 g of intermediate 1-5. Step 6: Intermediate preparation 1-6 Petition 870230062726, dated 07 / 18 / 2023, page 38 / 159 31 / 63

[048] 19.05 g of intermediate 1-5 and 8.287 g of anhydrous potassium carbonate were added to a single-necked flask and dissolved with 60 g of THF, and 7.566 g of dimethyl sulfate were added, followed by stirring overnight at room temperature. After the reaction was complete, the THF was centrifuged, extraction was performed with ethyl acetate, the anhydrous sodium sulfate was dried, and the organic phase was centrifuged to obtain 19.62 g of crude intermediate 1-6. Step 7: preparation of intermediate 1-7 < / ' f3c no I

[049] 19.62 g of intermediate 1-6 were dissolved in 150 ml of glacial acetic acid at room temperature, the same volume of 36% hydrochloric acid was added and a reflux reaction was carried out for 8 hours. After completion of the reaction, the excess solvent was evaporated under reduced pressure and water was added to the residue to precipitate the solid, followed by stirring and filtration. Filter cakes were washed with water three times and dried at 60°C to obtain 12.73 g of crude intermediate 1-7. Step 8: Intermediate preparation 1-8 Petition 870230062726, dated 07 / 18 / 2023, page 39 / 159 32 / 63

[050] 6.8 g of intermediate 1-7, 35 g of 1,2-dichloroethane, 1 drop of DMF and 3.316 g of dichlorosulfoxide were added to a 100 ml single-necked flask and subjected to a reflux reaction for 3 hours. After the reaction was complete, the excess dichlorosulfoxide and solvent were separated to obtain 6.22 g of crude intermediate 1-8. Example 2: preparation of compound 3 Step 1: Intermediate preparation 3-1

[051] Intermediate 1-8 (1 g) described in Example 1 and 320 mg of methyl glycolate were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 394 mg of triethylamine were added dropwise and then a reaction was carried out at room temperature for 2 hours. After completion of the reaction, purification by column chromatography was performed to obtain 1.02 g of intermediate 3-1. Step 2: Intermediate preparation 3-2

[052] 1.02 g of intermediate 3-1, 6.12 g of hydrochloric acid (36%) and 6.12 g of acetic acid were added to a reaction flask and refluxed for 40 minutes, and the reaction solution was centrifuged to obtain 1.01 g of intermediate 3-2. Step 3: Intermediate preparation 3-3 Petition 870230062726, dated 07 / 18 / 2023, page 40 / 159 33 / 63

[053] 1.01 g of intermediate 3-2, 340 mg of dichlorosulfoxide, 2 drops of DMF and 5.5 g of dichloroethane were added to a reaction flask, a reflux reaction was carried out for 3 hours and the reaction solution was centrifuged to obtain 1.02 g of intermediate 3-3. Step 4: Preparation of compound 3

[054] 103.29 mg of 2-methoxyethanol and 228.95 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen; 3 ml of dichloromethane solution from intermediate 3-3 (0.50 g) prepared in the last step were added dropwise and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 165 mg of compound 3. NMR (400 MHz, DMSO-de) δ 8.16 (d, J = 7.8 Hz, 1H), 7.95 (d, J = 9.6 Hz, 1H), 6.62 (s, 1H), 4.99 (s, 2H), 4.30 - 4.23 (m, 2H), 3.59 - 3.52 (m, 2H), 3.42 (s, 3H), 3.26 (s, 3H). LCMS (ESI) [M + H]+ = 483.05, Found = 482.61. Example 3: preparation of compound 10 Step 1: preparation of compound 10 Petition 870230062726, dated 07 / 18 / 2023, page 41 / 159 34 / 63

[055] 99.83 mg of 2-allyloxyethanol and 123.60 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 2.5 ml of dichloromethane solution of intermediate 3-3 (0.40 g) described in Example 2 were added dropwise and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 260 mg of light yellow oil as compound 10. NMR (400 MHz, DMSO-d6) δ 8.16 (d, J = 7.7 Hz, 1H), 7.94 (d, J = 9.6 Hz, 1H), 6.61 (s, 1H), 5.93 - 5.72 (m, 1H), 5.24 (dq, J = 17.4, 1.8 Hz, 1H), 5.13 (dt, J = 10.1, 1.6 Hz, 1H), 4.99 (s, 2H), 4.27 (dd, J = 5.6, 3.6 Hz, 2H), 3.96 (dt, J = 5.4, 1.6Hz, 2H), 3.67 - 3.55 (m, 2H). LCMS (ESI) [M + H]+=5 09.07, Found = 508.62. Example 4: preparation of compound 28 Step 1: preparation of compound 28

[056] 95.70 mg of propinol ethoxylate and 148.82 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 3 ml of dichloromethane solution of intermediate 3-3 (0.50 g) described in Example 2 were added dropwise, and then a reaction was carried out at room temperature for 2 hours. After the Petition 870230062726, dated 07 / 18 / 2023, page 42 / 159 35 / 63 conclusion of the reaction, purification by column chromatography was performed to obtain 110 mg of light yellow oil as compound 28. NMR (400 MHz, DMSO-d6) 5 8.15 (d, J= 7.7 Hz, 1H), 7.94 (d, J= 9.6 Hz, 1H), 6.61 (s, 1H), 4.98 (s, 2H), 4.27 (dd, J= 5.7, 3.4 Hz, 2H), 4.16 (d, J = 2.4 Hz, 2H), 3.75 - 3.63 (m, 2H), 3.43 (d, J = 11.5 Hz, 4H). LCMS (ESI) [M + H]+ =507.05, Found =506.83. Example 5: Intermediate preparation 54-3 Step 1: Intermediate preparation 54-1

[057] 20 g of intermediate 1-8 described in Example 1, 4.86 g of methyl D-lactate and 100 g of dichloromethane were added to a reaction flask, blown with nitrogen and stirred at room temperature. 5.9 g of triethylamine were added dropwise over 60 minutes, followed by overnight stirring at room temperature. After completion of the reaction, purification by column chromatography was performed to obtain 16 g of intermediate 54-1. Step 2: Intermediate preparation 54-2

[058] 15 g of intermediate 54-1, 90 g of hydrochloric acid (36%) and 90 g of acetic acid were added to a reaction flask and stirred at 60°C for 40 minutes until the reaction was complete, and the solvent was centrifuged to obtain 14 g of Petition 870230062726, dated 07 / 18 / 2023, page 43 / 159 36 / 63 intermediate 54-2. Step 3: Intermediate preparation 54-3

[059] 5.0 g of intermediate 54-2, 1.63 g of chloride sulfoxide, 25 g of 1,2-dichloroethane and 2 drops of DMF were added to a reaction flask for reflux stirring at 90°C. After one hour of reaction, the solvent was centrifuged to obtain 5.1 g of intermediate 54-3. Example 6: preparation of compound 54

[060] 0.6 g of intermediate 54-3 described in Example 5, 0.120 g of 2-methoxyethanol, 10 g of dichloromethane and 0.2 g of triethylamine were added to a reaction flask, blown with nitrogen and stirred at room temperature for 1 hour until the reaction was complete. After the reaction was complete, purification by column chromatography was performed to obtain 0.350 g of compound 54. NMR (400 MHz, CDCl3) δ 7.97 (dd, J = 7.7, 2.0 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 6.37 (s, 1H), 5.36 (q, J = 7.0 Hz, 1H), 4.32 (s, 2H), 3.60 (t, J = 4.6 Hz, 2H), 3.57 (s, 3H), 3.36 (s, 3H), 1.62 (d, J = 7.1 Hz, 3H). LCMS (ESI) [M + H]+ = 497.07, Found = 497.16. Example 7: preparation of compound 61 Step 1: preparation of compound 61 Petition 870230062726, dated 07 / 18 / 2023, page 44 / 159 37 / 63

[061] 290 mg of 2-allyloxyethanol and 330 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen; 10 ml of dichloromethane solution of intermediate 54-3 (1.0 g) described in Example 5 was added dropwise and then a reaction was carried out at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 800 mg of compound 61. NMR (400 MHz, DMSO-de) δ 8.14 (d, J = 7.8 Hz, 1H), 7.94 (d, J = 9.6 Hz, 1H), 6.62 (d, J = 3.0 Hz, 1H), 5.84 (ddtd, J = 16.9, 10.6, 5.3, 1.1 Hz, 1H), 5.31 (qt, J = 6.5, 3.3 Hz, 1H), 5.26 - 5.20 (m, 1H), 5.12 (dq, J = 10.4, 1.6 Hz, 1H), 4.34 - 4.20 (m, 2H), 3.95 (dt, J = 5.3, 1.5 Hz, 2H), 3.60 (ddd, J = 6.0, 4.2, 1.4 Hz, 2H), 3.45 - 3.40 (m, 3H), 1.53 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+ =523.08, Found =522.96. Example 8: preparation of compound 79 Step 1: preparation of compound 79

[062] 1 g of intermediate 54-3 described in Example 5 was dissolved in 5 ml of 1,2-dichloroethane, a solution of 1,2-dichloroethane propynol ethoxylate (220 mg) was added dropwise, the solution was stirred at 20°C for 10 minutes, and then 330 mg of triethylamine were added dropwise. After the reaction of the raw materials was completed in the test Petition 870230062726, dated 07 / 18 / 2023, p. 45 / 159 38 / 63 of LCMS, 20 ml of hydrochloric acid (IN) were added for washing, the solution was separated, the organic phase was dried with anhydrous sodium sulfate, and purification by column chromatography was performed to obtain 200 mg of colorless oily liquid as compound 79. NMR (400 MHz, Chloroform-d) δ 7.97 (dd, J = 7.7, 2.1 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 6.38 (d, J = 1.0 Hz, 1H), 5.36 (q, J = 7.1 Hz, 1H), 5.30 (s, 1H), 4.17 (dd, J = 2.4, 0.7 Hz, 2H), 3.76 (dt, J = 6.9, 3.0 Hz, 2H), 3.59 - 3.55 (m, 3H), 1.62 (dd, J = 7.1, 1.0 Hz, 3H), 1.33 - 1.23 (m, 2H). .LCMS (ESI) [M + H] + =521.07, Found =521.21. Example 9: preparation of compound 88 Step 1: preparation of compound 88

[063] 145.14 mg of 2-(methylthio)ethanol and 199.21 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen; 3 ml of dichloromethane solution of intermediate 54-3 (0.60 g) described in Example 5 were added dropwise and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 545 mg of colorless oil as compound 88. NMR (400 MHz, DMSO-de) δ 8.15 (d, J= 7.8 Hz, 1H) , 7.94 (d, J= 9.6 Hz, 1H) , 6.63 (d, J= 2.9 Hz, 1H) , 5.32 (dd, J= 7.0, 2.0 Hz, 1H) , 4.39 - 4.21 (m, 2H) , 3.42 (s, 3H), 2.83 - 2.66 (m, 2H), 2.11 - 2.07 (m, 3H), 1.55 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+ =512.04, Found =512.54. Example 10: preparation of compound 92 Petition 870230062726, dated 07 / 18 / 2023, page 46 / 159 39 / 63 Step 1: preparation of compound 92

[064] 250.0 mg of compound 88 and 10 ml of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 84.11 mg of m-chloroperoxybenzoic acid were added and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 177 mg of colorless oil as compound 92. ^-H NMR (400 MHz, DMSO-de) δ 8.22 (d, J = 7.7 Hz, 1H), 8.01 (d, J = 9.6 Hz, 1H), 6.70 (d, J = 2.9 Hz, 1H), 5.45 - 5.35 (m, 1H), 4.66 - 4.42 (m, 2H), 3.49 (s, 3H), 3.29 - 3.02 (m, 2H), 2.73 - 2.62 (m, 3H), 1.61 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+=529.04, Found =528.65. Example 11: preparation of compound 93 Step 1: preparation of compound 93

[065] 97.77 mg of 2-methylsulfonyl ethanol and 99.61 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen; 2 ml of dichloromethane solution of intermediate 54-3 (0.30 g) described in Example 5 were added dropwise, and a reaction was carried out at room temperature for 2 hours. After completion of the reaction, purification by column chromatography was performed. Petition 870230062726, dated 07 / 18 / 2023, page 47 / 159 40 / 63 was performed to obtain 192 mg of compound 93. NMR (400 MHz, DMSO-de) δ 8.16 (d, J = 7.7 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 6.63 (d, J = 3.2 Hz, 1H), 5.44 - 5.28 (m, 1H), 4.57 - 4.41 (m, 2H), 3.55 (t, J= 5.8 Hz, 2H), 3.02 (s, 3H), 1.54 (d, J= 7.0 Hz, 3H). LCMS (ESI) [M + H]+ =545.03, Found =544.58. Example 12: preparation of compound 96

[066] 0.5 g of intermediate 53-3 described in Example 5, 5 ml of dichloromethane, 97.2 mg of (S)-glycidol and 0.17 g of triethylamine were added to a 25 ml single-necked flask and shaken overnight at room temperature. After the reaction was complete, 5 ml of water were added, the solution was shaken and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. Purification by column chromatography was performed to obtain 215 mg of the compound. 96.¾ NMR (400 MHz, CDC13) δ 7.97 (d, J= 7.7 Hz, 1H), 7.40 (d, J = 9.1 Hz, 1H), 6.38 (d, J= 1.1 Hz, 1H), 5.37 (q, J= 7.0 Hz, 1H), 4.49 (dd, J= 12.2, 3.0 Hz, 1H), 4.07 - 3.94 (m, 1H), 3.57 (s, 3H), 3.22 (tt, J = 9.8, 4.9 Hz, 1H), 2.84 (q, J = 4.4 Hz, 1H), 2.63 (dd, J = 4.7, 2.6 Hz, 1H), 1.62 (t, J = 9.2 Hz, 3H). LCMS (ESI) [M + H] + =495.05, Found =495.05. Example 13: preparation of compound 97 Petition 870230062726, dated 07 / 18 / 2023, p. 48 / 159 41 / 63

[067] 0.5 g of intermediate 53-3 described in Example 5, 5 ml of dichloromethane, 97.2 mg of (R)-glycidol and 0.17 g of triethylamine were added to a 25 ml single-necked flask and shaken overnight at room temperature. After the reaction was complete, 5 ml of water were added, the solution was shaken and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. Purification by column chromatography was performed to obtain 330 mg of compound 97. NMR (400 MHz, CDC13) δ 7.97 (d, J= 7.7 Hz, 1H), 7.40 (d, J= 9.2 Hz, 1H), 6.37 (d, J= 2.3 Hz, 1H), 5.37 (qd, J= 7.1, 2.2 Hz, 1H), 4.49 (dd, J= 12.2, 2.2 Hz, 1H), 4.13 - 3.98 (m, 1H), 3.57 (d, J= 2.0 Hz, 3H), 3.20 (tt, J= 5.7, 2.8 Hz, 1H), 2.84 (t, J= 4.5 Hz, 1H), 2.67 (dt, J= 10.9, 5.6 Hz, 1H), 1.63 (d, J= 7.1 Hz, 3H). LCMS (ESI) [M + H]+ =495.05, Found =495.30. Example 14: Intermediate preparation 105-3 Step 1: Intermediate preparation 105-1

[068] 324.4 mg of methyl L-lactate were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, and the intermediate 1-8 (1 g) described in Example 1 was added dropwise, followed by 394 mg of triethylamine. The reaction was then carried out at room temperature for 2 hours. After completion of the reaction, purification by column chromatography was performed to obtain 923 g of the intermediate 105-1. Step 2: Intermediate preparation 105-2 Petition 870230062726, dated 07 / 18 / 2023, page 49 / 159 42 / 63

[069] 923 g of intermediate 105-1, 6.46 g of hydrochloric acid (36%) and 6.46 g of acetic acid were added to a reaction flask and refluxed for 40 minutes, and the reaction solution was centrifuged to obtain 900 g of intermediate 105-2. Step 3: Intermediate preparation 105-3

[070] 900 g of intermediate 105-2, 366, 49 mg of dichlorosulfoxide, 2 drops of DMF and 4.5 g of 1,2-dichloroethane were added to a reaction flask, a reflux reaction was carried out for 3 hours and the reaction solution was centrifuged to obtain 800 g of intermediate 105-3. Example 15: preparation of compound 105

[071] 0.6 g of the intermediate 105-3 described in Example 14, 0.120 g of 2-methoxyethanol, 10 g of dichloromethane, and 0.2 g of triethylamine were added to a reaction flask, blown with nitrogen, and stirred at room temperature for 1 hour until the reaction was complete. After the reaction was complete, purification by column chromatography was performed to obtain 0.40 g of compound 105. NMR (400 MHz, CDCl3) δ 7.97 (dd, J = Petition 870230062726, dated 07 / 18 / 2023, page 50 / 159 43 / 63 7.7, 2.0 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 6.37 (s, 1H), 5.36 (q, J = 7.0 Hz, 1H), 4.32 (s, 2H), 3.60 (t, J = 4.6 Hz, 2H), 3.57 (s, 3H), 3.36 (s, 3H), 1.62 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H] + =497.07, Found =497.34. Example 16: preparation of compound 112

[072] The intermediate 105-3 (1 g) described in Example 14 was added and weighed into a 25 ml single-necked flask, along with 10 ml of dichloromethane, 268 mg of 2-allyloxyethanol, and 330 mg of triethylamine, followed by stirring at room temperature to allow reaction. After 15 hours, the reaction was complete in the LCMS test. 5 ml of water were 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 purification by column chromatography (PE: EA=4:1), 768 mg of colorless oily liquid were obtained as compound 112. ^-H NMR (400 MHz, CDC13) δ 7.97 (dd, J= 7.7, 1.9 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 6.37 (s, 1H), 5.87 (ddd, J = 22.7, 10.7, 5.6 Hz, 1H), 5.35 (t, J= 7.0 Hz, 1H), 5.27 (dd, J= 17.2, 1.5 Hz, 1H), 5.18 (d, J= 10.4 Hz, 1H), 4.43 - 4.24 (m, 2H), 4.00 (d, J = 5.4 Hz, 2H), 3.65 (t, J = 4.8 Hz, 2H), 3.57 (s, 3H), 1.62 (d, J = 7.1 Hz, 3H).LCMS (ESI) [M + H]+ =523.08, Found =523.10. Example 17: preparation of compound 130 Petition 870230062726, dated 07 / 18 / 2023, p. 51 / 159 44 / 63

[073] 1 g of intermediate 105-3 described in Example 5 was dissolved in 14 ml of 1,2-dichloroethane, a solution of 1,2-dichloroethane of propinol ethoxylate (220 mg) was added dropwise, the solution was stirred at 20°C for 10 minutes and then 330 mg of triethylamine were added dropwise. After the reaction of the raw materials was completed in the LCMS test, 20 ml of hydrochloric acid (IN) were added for washing, the solution was separated, the organic phase was dried with anhydrous sodium sulfate, and purification by column chromatography was performed to obtain 230 mg of colorless oily liquid as compound 130. NMR (400 MHz, Chloroform-d) δ 7.97 (dd, J = 7.7, 2.1 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 6.38 (d, J = 1.0 Hz, 1H), 5.36 (q, J = 7.1 Hz, 1H), 5.30 (s, 1H), 4.17 (dd, J = 2.4, 0.7 Hz, 2H), 3.76 (dt, J = 6, 9, 3.0 Hz, 2H), 3.59 - 3.55 (m, 3H), 1.62 (dd, J = 7.1, 1.0 Hz, 3H), 1.33 - 1.23 (m, 2H). .LCMS (ESI) [M + H] + =521.07, Found =521.12. Example 18: preparation of compound 139 Step 1: preparation of compound 139

[074] 145.14 mg of 2-(methylthio)ethanol and 199.21 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen; 3 ml of dichloromethane solution of intermediate 105-3 (0.60 g) described in Example 14 were added dropwise, and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 419 mg of colorless oil as Petition 870230062726, dated 07 / 18 / 2023, page 52 / 159 45 / 63 compound 139. NMR (400 MHz, DMSO-de) δ 8.15 (d, J = 7.8 Hz, 1H), 7.94 (d, J=9.6Hz, 1H), 6.63 (d, J=2.9Hz, 1H), 5.32 (dd, J = Ί,Ο, 2.0 Hz, 1H), 4.39 - 4.21 (m, 2H), 3.42 (s, 3H), 2.83 2.66 (m, 2H), 2.11-2.07 (m, 3H), 1.55 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+ =512.04, Found =512.54. Example 19: Preparation of compound 143 Step 1: Preparation of compound 143

[075] 250.0 mg of compound 139 described in Example 18 and 10 ml of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 84.11 mg of m-chloroperoxybenzoic acid were added and then a reaction was carried out at room temperature for 2 hours. After completion of the reaction, purification by column chromatography was performed to obtain 170 mg of colorless oil as compound 143. ^-H NMR (400 MHz, DMSO-DE) 4.70 - 4.43 (m, 2H), 3.48 (s, 3H), 3.27 - 3.00 (m, 2H), 2.65 (d, J = 2.6 Hz, 3H), 1.61 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+=529.04, Found =528.65. Example 20: preparation of compound 144 Step 1: preparation of compound 144 Petition 870230062726, dated 07 / 18 / 2023, page 53 / 159 46 / 63

[076] 97.77 mg of 2-methylsulfonyl ethanol and 99.61 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen; 2 ml of dichloromethane solution of intermediate 105-3 (0.30 g) described in Example 14 were added dropwise and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 166 mg of compound 144. NMR (400 MHz, DMSO-de) δ 8.16 (d, J= 7.7 Hz, 1H) , 7.94 (d, J= 9.5 Hz, 1H) , 6.63 (d, J= 3.2 Hz, 1H) , 5.43 - 5.32 (m, 1H) , 4.57 - 4.41 (m, 2H) , 3.55 (t, J= 5.8 Hz, 2H) , 3.02 (s, 3H) , 1.54 (d, J= 7.2 Hz, 3H). LCMS (ESI) [M + H]+ =545.03, Found =544.58. Example 21: preparation of compound 147 [°77] 0.5 g of the intermediate 105-3 described in Example 14, 5 ml of dichloromethane, 97.2 mg of (S)-glycidol and 0.17 g of triethylamine were added to a 25 ml single-necked flask and shaken overnight at room temperature. After the reaction was complete, 5 ml of water were added, the solution was shaken and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. Purification by column chromatography was performed to obtain 215 mg of compound 147. NMR (400 MHz, CDC13) δ 7.97 (d, J= 7.7 Hz, 1H), 7.40 (d, J= 9.1 Hz, 1H), 6.38 (d, J=1.1Hz, 1H), 5.37 (q, J=7.0Hz, 1H), 4.49 (dd, J= 12.2, 3.0 Hz, 1H), 4.07 - 3.94 (m, 1H), 3.57 (s, 3H), 3.22 (tt, J= 9.8, 4.9 Hz, 1H), 2.84 (q, J= 4.4 Hz, 1H), 2.63 (dd, Petition 870230062726, dated 07 / 18 / 2023, page 54 / 159 47 / 63 <7=4.7, 2.6 Hz, 1H), 1.62 (t, J = 9.2 Hz, 3H). LCMS (ESI) [M + H] + =495.05, Found =495.12. Example 22: preparation of compound 148

[078] 0.5 g of the intermediate 105-3 described in Example 14, 5 ml of dichloromethane, 97.2 mg of (R)-glycidol and 0.17 g of triethylamine were added to a 25 ml single-necked flask and shaken overnight at room temperature. After the reaction was complete, 5 ml of water were added, the solution was shaken and separated to obtain an organic phase, the organic phase was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. Purification by column chromatography was performed to obtain 240 mg of compound 148. NMR (400 MHz, CDC13) δ 7.97 (d, J= 7.7 Hz, 1H), 7.40 (d, J= 9.1 Hz, 1H), 6.37 (d, J= 2.2 Hz, 1H), 5.37 (dd, J= 7.1, 2.1 Hz, 1H), 4.49 (dd, J= 12.2, 2.3 Hz, 1H), 407 (ddd, J= 12.2, 5.9, 2.0 Hz, 1H), 3.57 (d, J = 1.9 Hz, 3H), 3.20 (tt, J = 5.8, 2.8 Hz, 1H), 2.83 (t, J= 4.5 Hz, 1H) , 2.72 - 2.62 (m, 1H) , 1.63 (d, J= 7.1 Hz, 3H). LCMS (ESI) [M + H]+ =495.05, Found =495.06. Example 23: Intermediate preparation 156-3 Step 1: Intermediate preparation 156-1

[079] 20.0 g of intermediate 1-8 were added Petition 870230062726, dated 07 / 18 / 2023, page 55 / 159 48 / 63 described in Example 1, 4.86 g of methyl lactate and 100 g of dichloromethane were placed in a reaction flask, blown with nitrogen, and stirred at room temperature. 5.9 g of triethylamine were added dropwise over 60 minutes, followed by overnight stirring at room temperature. After the reaction was complete, purification by column chromatography was performed to obtain 15.8 g of intermediate 156-1. Step 2: Intermediate preparation 156-2 F / ¾. ,CI FoC^N^O ° I

[080] 15.0 g of intermediate 22-1, 90 g of hydrochloric acid (36%) and 90 g of acetic acid were added to a reaction flask and stirred at 60°C for 40 minutes until the reaction was complete, and the solvent was centrifuged to obtain 13.7 g of intermediate 156-2. Step 3: Intermediate preparation 156-3

[081] 900 g of intermediate 156-2, 366, 49 mg of dichlorosulfoxide, 2 drops of DMF and 4.5 g of 1,2-dichloroethane were added to a reaction flask, a reflux reaction was carried out for 3 hours and the reaction solution was centrifuged to obtain 820 g of intermediate 156-3. Example 24: preparation of compound 156 Petition 870230062726, dated 07 / 18 / 2023, page 56 / 159 49 / 63 0.6 g of the intermediate 156-3 described in Example 23, 0.120 g of 2-methoxyethanol, 10 g of dichloromethane, and 0.2 g of triethylamine were added to a reaction flask, blown with nitrogen, and stirred at room temperature for 1 hour until the reaction was complete. After the reaction was complete, purification by column chromatography was performed to obtain 0.395 g of compound 156. NMR (400 MHz, CDCl3) δ 7.97 (dd, J = 7.7, 2.0 Hz, 1H), 7.40 (d, J = 9.2 Hz, 1H), 6.37 (s, 1H), 5.36 (q, J = 7.0 Hz, 1H), 4.32 (s, 2H), 3.60 (t, J = 4.6 Hz, 2H), 3.57 (s, 3H), 3.36 (s, , 3H), 1.62 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H] + = 4 97.07, Found = 497.30. Example 25: preparation of compound 163 With reference to the methods of Examples 7 and 16, compound 163 was prepared using intermediate 156-3 described in Example 23 and 2-allyloxyethanol. Example 26: preparation of compound 181

[083] With reference to the methods of Examples 8 and 17, compound 181 was prepared using intermediate 156-3 described Petition 870230062726, dated 07 / 18 / 2023, p. 57 / 159 50 / 63 in Example 23 and propinol ethoxylate. NMR (400 MHz, Chlorine form!) 5.30 (s, 1H) 1.33 - 1.23 (m, 2H) . . LCMS (ESI) [M + H]+ =521.07, Found =521.11. Example 27: preparation of compound 190 Step 1: Preparation of compound 190

[084] 145.14 mg of 2-(methylthio)ethanol and 199.21 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen; 3 ml of dichloromethane solution of intermediate 156-3 (0.60 g) described in Example 23 were added dropwise and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 409 mg of colorless oil as compound 190. ^-H NMR (400 MHz, DMSO-d) δ 8.15 (d, J = 7.8 Hz, 1H), 7.94 (d, J = 9.6 Hz, 1H), 6.63 (d, J = 2.9 Hz, 1H), 5.32 (dd, J = 7.0, 2.0 Hz, 1H), 4.39 - 4.21 (m, 2H), 3.42 (s, 3H), 2.83 - 2.66 (m, 2H), 2.11 - 2.07 (m, 3H), 1.55 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+ =512.04, Found =512.54. Example 28: preparation of compound 194 Step 1: preparation of compound 194 Petition 870230062726, dated 07 / 18 / 2023, pp. 58 / 159 51 / 63 250.0 mg of compound 190 and 10 ml of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 84.11 mg of m-chloroperoxybenzoic acid were added, and then a reaction was carried out at room temperature for 2 hours. After the reaction was complete, purification by column chromatography was performed to obtain 166 mg of colorless oil as compound 194. NMR (400 MHz, DMSO-de) δ 8.21 (d, J= 7.7 Hz, 1H), 8.01 (d, J= 9.6 Hz, 1H), 6.70 (d, J = 2.8 Hz, 1H), 5.41 (qt, J = 7.2, 1.6 Hz, 1H), 4.70 - 4.43 (m, 2H), 3.48 (s, 3H), 3.27 - 3.00 (m, 2H), 2.65 (d, J = 2.6 Hz, 3H), 1.61 (d, J = 7.0 Hz, 3H). LCMS (ESI) [M + H]+ =529.04, Found =528.65. Example 29: preparation of compound 195 Step 1: preparation of compound 195

[085] 97.77 mg of 2-methylsulfonyl ethanol and 99.61 mg of triethylamine were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen; 2 ml of dichloromethane solution of intermediate 156-3 (0.30 g) described in Example 23 were added dropwise, and a reaction was carried out at room temperature for 2 hours. After completion of the reaction, purification by column chromatography was performed to obtain 168 mg of compound 195. ^-H NMR (400 MHz, Petition 870230062726, dated 07 / 18 / 2023, pp. 59 / 159 52 / 63 DMSO-de) δ 8.16 (d, J = 7.7 Hz, 1H), 7.94 (d, J = 9.5 Hz, 1H), 6.63 (d, J = 3.2 Hz, 1H), 5.43 - 5.32 (m, 1H), 4.57 - 4.41 (m, 2H), 3.55 (t, J = 5.8 Hz, 2H), 3.02 (s, 3H), 1.54 (d, J = 7.2 Hz, 3H). LCMS (ESI) [M + H]+ =545.03, Found =544.58. Example 30: preparation of compound 198

[086] With reference to the methods of Examples 12 and 21, compound 198 was prepared using intermediate 156-3 described in Example 23 and (S)-glycidol. ^-H NMR (400 MHz, CDCI3) δ 7.97 (d, J= 7.7 Hz, 1H), 7.40 (d, J = 9.1 Hz, 1H), 6.38 (d, J = 1.1 Hz, 1H), 5.37 (q, J = 7.0 Hz, 1H), 4.49 (dd, J = 12.2, 3.0 Hz, 1H), 4.07 - 3.94 (m, 1H), 3.57 (s, 3H), 3.22 (tt, J = 9.8, 4.9 Hz, 1H), 2.84 (q, J = 4.4 Hz, 1H), 2.63 (dd, J= 4.7, 2.6Hz, 1H) , 1.62 (t, J = 9.2 Hz, 3H). LCMS (ESI) [M + H] + =495.05, Found =495.04. Example 31: preparation of compound 199

[087] With reference to the methods of Examples 13 and 22, compound 199 was prepared using intermediate 156-3 described in Example 23 and (R)-glycidol. ^-H NMR (400 MHz, CDCI3) δ 7.97 (d, J= 7.7 Hz, 1H), 7.40 (d, J= 9.2 Hz, 1H), 6.37 (d, J= 2.3 Hz, 1H), 5.37 (qd, J= 7.1, 2.2 Hz, 1H), 4.49 (dd, J = 12.2, 2.2 Hz, 1H), 4.13 - 3.98 (m, 1H), 3.57 (d, J= 2.0 Hz, 3H), 3.20 (tt, J= 5.Ί, 2.8 Hz, 1H), 2.84 (t, J= 4.5 Hz, 1H), 2.67 Petition 870230062726, dated 07 / 18 / 2023, p. 60 / 159 53 / 63 (dt, J = 10.9, 5.6 Hz, 1H), 1.63 (d, J = 7, 1 Hz, 3H). LCMS (ESI) [M + H] + =495.05, Found =495.20. Example 32: preparation of compound 207 Step 1: Intermediate preparation 207-1

[088] 2.36 g of methyl 2-hydroxyisobutyrate, 1.91 g of DMAP, and 50 g of dichloromethane were added to a reaction flask, which was then nitrogen-blown and stirred at room temperature. 5 g of intermediate 1-8 described in Example 1 were added dropwise over 20 minutes, followed by stirring at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 3.57 g of intermediate 207-1. Step 2: Intermediate preparation 207-2

[089] 3.57 g of intermediate 207-1, 20 g of hydrochloric acid (36%) and 20 g of acetic acid were added to a reaction flask and stirred at 120°C for 2 hours. After the reaction was complete, the reaction solution was poured into 100 ml of ice-cold water, extraction was performed with EA, and the organic phase was centrifuged to obtain 2.78 g of intermediate 207-2. Step 3: preparation of compound 207-3 Petition 870230062726, dated 07 / 18 / 2023, page 61 / 159 54 / 63

[090] 2.78 g of intermediate 207-2, 1.1 g of chloride sulfoxide, 30 g of 1,2-dichloroethane and 2 drops of DMF were added to a reaction flask for reflux stirring at 90°C. After one hour of reaction, the solvent was centrifuged to obtain 3.2 g of intermediate 207-3. Step 4: preparation of compound 207

[091] 0.3 g of intermediate 207-3, 0.054 g of 2-methoxyethanol, 10 g of dichloromethane and 0.089 g of triethylamine were added to a reaction flask, blown with nitrogen and stirred at room temperature. After the reaction was complete, 5 ml of water were 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 performed to obtain 120 mg of white solid as compound 207. NMR (400 MHz, CDCl3) δ 7.86 (d, J = 7.7 Hz, 1H), 7.38 (d, J = 9.2 Hz, 1H), 6.38 (s, 1H), 4.50 - 4.18 (m, 2H), 3.59 (s, 2H), 3.57 (s, 3H), 3.32 (s, 3H), 1.69 (s, 6H). LCMS (ESI) [M + H]+ = 511.08, Found = 511.12. Example 33: preparation of compound 214 Step 1: preparation of compound 214 Petition 870230062726, dated 07 / 18 / 2023, page 62 / 159 55 / 63

[092] 1.04 g of 2-allyloxyethanol, 1.24 g of DMAP and 30 g of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen; 20 ml of dichloromethane solution of intermediate 207-3 (3.2 g) described in Example 32 were added dropwise and then a reaction was carried out at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 600 mg of compound 214. NMR (400 MHz, DMSO-de) δ 8.07 (d, J= 7.8 Hz, 1H), 7.92 (d, J= 9.6 Hz, 1H), 6.63 (s, 1H), 5.90 - 5.73 (m, 1H), 5.25 - 5.08 (m, 2H), 4.27 - 4.19 (m, 2H), 3.91 (dt, J=5.3, 1.6 Hz, 2H), 3.59 - 3.55 (m, 2H), 3.42 (d, J=1.3 Hz, 3H), 1.63 (s, 6H).LCMS (ESI) [M + H] + =537.10, Found =536.98. Example 34: preparation of compound 249

[093] 0.71 g of (S)-glycidol, 0.5 g of DMAP, 2 g of triethylamine, and 2 mL of dichloromethane were added to a reaction flask, cooled in an ice bath, and blown with nitrogen. 2.57 g of the intermediate 207-3 described in Example 32 were added dropwise to dissolve in 20 mL of dichloromethane solution, and a reaction was carried out at room temperature for 3 hours. After the reaction was complete, purification by column chromatography was performed to obtain 3 g of compound. Petition 870230062726, dated 07 / 18 / 2023, page 63 / 159 56 / 63 oily as compound 249. NMR (400 MHz, Chloroform-d) δ 7.87 (d, J= 7.6 Hz, 1H), 7.39 (d, J= 9.1 Hz, 1H), 6.38 (s, 1H), 4.45 (dd, J= 12.2, 3.4 Hz, 1H), 4.04 (dd, J = 12.2, 6.0 Hz, 1H), 3.57 (s, 3H), 3.21 (dq, J = 6.4, 3.3 Hz, 1H), 2.83 (t, J = 4.5 Hz, 1H), 2.64 (dd, <7=4.9, 2.6Hz, 1H), 1.70 (s, 6H). LCMS (ESI) [M + H] + =509.07, Found =508.93. Example 35: preparation of compound 250

[094] 0.71 g of (R)-glycidol, 0.5 g of DMAP, 2 g of triethylamine and 2 ml of dichloromethane were added to a reaction flask, cooled in an ice bath and blown with nitrogen. 20 ml of dichloromethane solution of 2.57 g of intermediate 207-3 described in Example 32 were added dropwise, and a reaction was carried out at room temperature for 3 hours. After the reaction was complete, purification by column chromatography was performed to obtain 2.9 g of oily compound as compound 250. ^-H NMR (400 MHz, Chloroform-d) 4.04 (dd, <7=12.2, 6.0 Hz, 1H), 3.56 (s, 3H), 3.20 (dq, <7= 6.1, 3.5 Hz, 1H), 2.82 (t, <7= 4.5 Hz, 1H), 2.63 (dd, <7= 4.8, 2.6Hz, 1H), 1.70 (s, 6H). LCMS (ESI) [M + H] + =509.07, Found =509.10. Example 36: preparation of compound 251 Step 1: preparation of compound 251 Petition 870230062726, dated 07 / 18 / 2023, p. 64 / 159 57 / 63

[095] With reference to the methods of Examples 34 and 35, compound 251 was prepared using intermediate 207-3 described in Example 32 and glycidol. ^-H NMR (400 MHz, Chloroform-d) δ 7.87 (d, J= 7.6 Hz, 1H), 7.39 (d, J= 9.1 Hz, 1H), 6.38 (s, 1H), 4.45 (dd, J= 12.2, 3.4 Hz, 1H), 4.04 (dd, J= 12.2, 6.0 Hz, 1H), 3.57 (s, 3H), 3.21 (dq, J= 6.4, 3.3 Hz, 1H), 2.83 (t, J= 4.5 Hz, 1H), 2.64 (dd, J= 4.9, 2.6 Hz, 1H), 1.70 (s, 6H). LCMS (ESI) [M + H] + =509.07, Found =508.97. Example 37: preparation of compound 258 Step 1: preparation of compound 258-1 0.6 g of methyl 1-hydroxy-1-cyclopropane carboxylate, 0.57 g of DMAP, and 25 g of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred, and blown with nitrogen. Then, 10 ml of dichloromethane solution of intermediate 1-8 (1.22 g) described in Example 1 were added dropwise, and a reaction was carried out at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 1.1 g of intermediate 258-1. Step 2: preparation of compound 258-2 Petition 870230062726, dated 07 / 18 / 2023, page 65 / 159 58 / 63

[096] 1.1 g of intermediate 258-1, 8 g of hydrochloric acid (36%) and 8 g of acetic acid were added to a reaction flask and stirred at 110°C for 4 hours. After the reaction was complete, the reaction solution was poured into 100 ml of ice-cold water, extraction was performed with EA and the organic phase was centrifuged to obtain 1.06 g of intermediate 258-2. Step 3: preparation of compound 258-3

[097] 1.06 g of intermediate 258-2 was added, 0.42 g of chloride sulfoxide, 20 g of 1,2-dichloroethane and 2 drops of DMF were added to a reaction flask for reflux stirring at 90°C. After one hour of reaction, the solvent was centrifuged to obtain 1.1 g of intermediate 258-3. Step 4: preparation of compound 258

[098] 0.211 g of 2-methoxyethanol, 0.323 g of triethylamine and 15 g of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 10 ml of dichloromethane solution from intermediate 258-3 (1.0 g) were added dropwise and then, Petition 870230062726, dated 07 / 18 / 2023, page 66 / 159 59 / 63 a reaction occurred at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 201 mg of compound 258. ^-H NMR (400 MHz, DMSO-de) δ 8.21 (d, J = 7.6 Hz, 1H), 8.01 (d, J = 9.4 Hz, 1H), 6.70 (s, 1H), 4.29 (t, J = 4.7 Hz, 2H), 3.57 (t, J = 4.6 Hz, 2H), 3.49 (s, 3H), 3.29 (s, 3H), 1.67-1.48 (m, 4H).LCMS (ESI) [M+H]+ = 509.07, Found = 508.92. Example 38: preparation of compound 300 Step 1: Preparation of compound 300

[099] 0.308 g of (S)-glycidol, 0.485 g of triethylamine and 20 g of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 15 ml of dichloromethane solution of intermediate 258-3 (1.5 g) described in Example 37 were added dropwise and then a reaction was carried out at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 212 mg of compound 300. NMR (400 MHz, DMSO-d6) δ 8.22 (d, J = 7.8 Hz, 1H), 8.01 (d, J = 9.6 Hz, 1H), 6.69 (s, 1H), 4.52 (dd, J = 12.3, 2.6 Hz, 1H), 4.03 (dd, J = 12.3, 6.3 Hz, 1H), 3.51-3.45 (m, 3H), 3.24 (ddt, J = 6.7, 4.2, 2.6 Hz, 1H), 2.83 (dd, J = 5.0, 4.2 Hz, 1H), 2.68 (dd, J = 5.0, 2.6 Hz, 1H), 1.68-1.51 (m, 4H). LCMS (ESI) [M + H]+ =507.05, Found =506.96. Example 39: preparation of compound 301 Step 1: Preparation of compound 301 Petition 870230062726, dated 07 / 18 / 2023, page 67 / 159 60 / 63

[0100] 0.205 g of (R)-glycidol, 0.323 g of triethylamine and 15 g of dichloromethane were added to a reaction flask, cooled in an ice bath, stirred and blown with nitrogen, 15 ml of dichloromethane solution of intermediate 258-3 (1.0 g) described in Example 37 were added dropwise and then a reaction was carried out at room temperature for 1 hour. After the reaction was complete, purification by column chromatography was performed to obtain 222 mg of compound 301. ^-H NMR (400 MHz, DMSO-de) δ 8.15 (d, J = 7.8 Hz, 1H), 7.94 (d, J = 9.6 Hz, 1H), 6.63 (s, 1H), 4.46 (dd, J = 12.3, 2.7 Hz, 1H), 3.97 (dd, J = 12.3, 6.2 Hz, 1H), 3.46 - 3.40 (m, 3H), 3.18 (ddt, J = 6.7, 4.2, 2.6 Hz, 1H), 2.77 (dd, J = 5.0, 4.3 Hz, 1H), 2.62 (dd, J = 5.0, 2.6 Hz, 1H), 1.61-1.45 (m, 4H). LCMS (ESI) [M + H] + =507.05, Found =507.10. Example 40: preparation of compound 302 Step 1: Preparation of compound 302

[0101] With reference to the methods of Examples 38 and 39, compound 302 was prepared using intermediate 258-3 described in Example 37 and glycidol. ^-H NMR (400 MHz, DMSO-de) δ 8.22 (d, J= 7.8 Hz, 1H) , 8.01 (d, J= 9.6 Hz, 1H) , 6.69 (s, 1H) , 4.52 (dd, J=12.3, 2.6 Hz, 1H) , 4.03 (dd, J=12.3, 6.3 Hz, 1H) , 3.51 - 3.45 (m, 3H), 3.24 (ddt, J= 6.7, 4.2, 2.6 Hz, 1H), 2.83 Petition 870230062726, dated 07 / 18 / 2023, p. 68 / 159 61 / 63 (dd, J = 5.0, 4.2 Hz, 1H), 2.68 (dd, J = 5.0, 2.6 Hz, 1H), 1.68 - 1.51 (m, 4H).LCMS (ESI) [M + H] + =507.05, Found =506.88. Example 41: greenhouse experiments

[0102] A method for testing herbicidal activity for the compounds of the present invention was as follows:

[0103] Seed treatment; pre-emergence: quantitative seeds of grasses (Echinochloa crusgalli, Eleusine indica, Digitaria sanguinalis, Alopecurus japonicus, Beckmannia syzigachne, Leptochloa chinensis, Polypogon fugax, Alopecurus aequalis, folium multiflorum and Poa annua), broadleaf weeds (Eclipta prostrata, Amaranthus retroflexus, Brassica juncea, Malachium aquaticum, Conyza canadensis and Sesbania cannabina) and Cyperus iria were sown in plastic pots with a diameter of 7 cm and holes in the bottom and filled with nutrient soil (sandy soil, pH 6.1, organic matter 1%) respectively, the seeds were covered with an adequate amount of soil after sowing;Next, the soil was moistened with water from the bottom, the seeds were grown in a lighted grow room at a constant temperature for 24 hours, and the soil was sprayed using a 3WP-2000 mobile spray tower produced by the Nanjing Institute of Agricultural Mechanization of the Ministry of Agriculture, in which the rotation speed of a main shaft was 96 mm / r, the spraying height was 300 mm, the effective spraying range of a nozzle was 350 mm, the spraying area was 0.35 m2, and the flow rate at the nozzle was 390 ml / minute.

[0104] Post-emergence: an adequate quantity of grass seeds (Echinochloa crusgalli, Eleusine indica, Digitaria sanguinalis, Alopecurus japonicus, Beckmannia syzigachne, Leptochloa chinensis, Polypogon fugax, Alopecurus Petition 870230062726, dated 07 / 18 / 2023, page 69 / 159 aequalis, Lolium multiflorum and Poa annua), broadleaf weeds {Eclipta prostrata, Amaranthus retroflexus, Brassica juncea, Malachium aquaticum, Conyza canadensis and Sesbania cannabina) and Cyperus iria were sown in plastic pots with a diameter of 7 cm and holes in the bottom and filled with nutrient soil (sandy soil, pH 6.1, 1% organic matter) respectively, the seeds were covered with an adequate amount of soil after sowing; then the soil was moistened with water from the bottom, the seeds were grown in a well-lit grow room with constant temperature until the 2-4 leaf stage, and the stems and leaves were treated with spray. After treatment, the test materials were placed in a laboratory and cultured in a lit culture room at a constant temperature after the liquid had dried naturally in the shade, and the results were determined 21 days later.

[0105] Classification standards for prevention and control purposes: A indicates that the inhibition rate was greater than or equal to 85% to 100%; B indicates that the inhibition rate was greater than or equal to 70% and less than 85%; C indicates that the inhibition rate was greater than or equal to 55% to less than 70%; D indicates that the inhibition rate was less than 55%.

[0106] Test results showed that compounds of general formula (I) generally had excellent prevention and control effects on various weeds at a dose of 30 g ai / hm2, reaching class A.

[0107] According to the test method above, a parallel experiment was carried out on herbicidal activities of Petition 870230062726, dated 07 / 18 / 2023, p. 70 / 159 63 / 63 some compounds of the general formula (I), the compound Butafenacil (compound 47 in the patent description report) specifically disclosed in US5183492A, and the compound CK (compound 1 in the patent description report) specifically disclosed in US5183492A, at application rates of 7.5 g ai / ha and 15 g ai / ha. The results were shown in Table 2: Table 2: Herbicidal activities of some compounds of the general formula (I) and control compounds (post-emergence, fresh weight inhibition rate) Compound number Dose ai / ha Alopecurus j aponicus Polypogon fugax Sesbania cannabina 3 7.5 BBA 15 AAA 105 7.5 ABA 15 AAA 207 7.5 AAA 15 AAA 214 7.5 AAA 15 AAA 258 7.5 AAA 15 AAA Butafenacil 7.5 DDC 15 DCB CK 7.5 DDC 15 CCB

[0108] The above descriptions are preferred embodiments of the present invention. It should be noted that, for those skilled in the art, many variations and improvements can be made without departing from the concept of the present invention, and such variations and improvements fall within the scope of protection of the present invention.

Claims

1. URACIL COMPOUND CONTAINING A CARBOXYLATE FRAGMENT, characterized by having the general formula (I): wherein, in the formula: Ri and R2 are selected from hydrogen or methyl, respectively; or Ri and R2 together with the carbon atom to which they are attached form a 3-membered carbocycle; R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkynexy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C1-3 alkyl S(0)n C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl; n=0, 1 or 2; And when R1 is selected from hydrogen and R2 is selected from methyl, the chiral carbon atom connected to it can be selected from an R configuration or an S configuration, or a mixture of the two; and, in the mixture, the ratio of R to S is 1:99 to 99:

1.

2. COMPOUND, according to claim 1, characterized in that: R1 and R2 are selected from hydrogen or methyl, respectively; or R1 and R2 together with the carbon atom to which they are attached form a 3-membered carbocycle; R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl; And when R1 is selected from hydrogen and R2 is selected from methyl, the chiral carbon atom connected to it may be selected from an R configuration or an S configuration, or a mixture of the two; and, in the mixture, the ratio of R to S being from 1:99 to 99:

1.

3. COMPOUND, according to claim 1, characterized in that: R1 and R2 are selected from hydrogen or methyl, respectively; R3 is selected from C1-3 alkoxy C1-3 alkyl, C1-3 haloalkoxy C1-3 alkyl, C2-6 alkenoxy C1-3 alkyl, C2-6 haloalkenoxy C1-3 alkyl, C2-6 alkynexy C1-3 alkyl, C2-6 haloalkynoxy C1-3 alkyl, C3-6 oxygen-containing cycloalkyl C1-3 alkyl, or C3-9 oxygen-containing cycloalkyl; and when R1 is selected from hydrogen and R2 is selected from methyl, the chiral carbon atom connected to it can be selected from an R configuration or an S configuration, or a mixture of the two; and, in the mixture, the ratio of R to S is from 1:99 to 99:

1.

4. METHOD FOR PREPARING THE URACIL COMPOUND CONTAINING A CARBOXYLATE FRAGMENT, as defined in any one of claims 1 to 3, characterized in that the method comprises a contact reaction between the carboxylic acid compound shown in formula (II) and the different substituted alcohol, halogenated or sulfonate compound in the presence of a solvent, Petition 870230062726, dated 07 / 18 / 2023, page 73 / 159 3 / 3 (II)(I) wherein in general formulas (I) and (II), the definitions of Ri, R2 and R3 are the same as in claim 1.

5. METHOD, according to claim 4, characterized in that the reaction temperature is from 0 to 160°C.

6. METHOD, according to claim 4, characterized by a reaction time of 2 to 15 hours.

7. METHOD, according to claim 4, characterized in that the reaction solvent is selected from at least one of dichloromethane, 1,2-dichloroethane, tetrahydrofuran, acetonitrile, 1,4-dioxane, toluene, o-xylene, m-xylene, p-xylene, n-heptane, n-octane and n-nonane.

8. METHOD, according to claim 4, characterized in that the molar ratio of the carboxylic acid compound shown in formula (II) to the different substituted, halogenated or sulfonate alcohol compound is 1:(1-4).

9. USE OF THE URACIL COMPOUND CONTAINING A CARBOXYLATE FRAGMENT, as defined in any one of claims 1 to 3, characterized by its use in the prevention and control of weeds.

10. COMPOSITION, characterized by comprising the uracil compound containing a carboxylate fragment, as defined in any one of claims 1 to 3, as the active ingredient, wherein the percentage by weight of the active ingredient in the composition is from 0.1% to 99.9%.