A triketone-quinazolinone compound, a preparation method and application thereof, and a herbicide

Abstract

The present application relates to the field of pesticide compounds, discloses a triketone-quinazoline diketone compound and a preparation method and application thereof and a herbicide, the compound has the structure shown in formula (I). The compound provided by the present application has excellent herbicidal effect and good safety to food crops and economic crops.

Description

Technical Field

[0001] This invention relates to the field of pesticides and herbicides, specifically to a trione-quinazolinedione compound, its preparation method and application, and a herbicide. Background Technology

[0002] The development and application of highly effective herbicides are important technical means to ensure grain yield and safeguard national food security.

[0003] However, the long-term, single, and unreasonable use of herbicides has led to the rampant growth of resistant weeds. Herbicide resistance has become a major problem restricting agricultural production, and there is an urgent need to independently develop new and efficient herbicides.

[0004] p-Hydroxypyruvate dioxygenase (HPPD) is one of the most important herbicide targets. Herbicides targeting HPPD have advantages such as high efficiency, low toxicity, low residue, good environmental compatibility, and slow resistance development. They also have excellent control efficacy against ALS, ACCase, and glyphosate weeds.

[0005] Therefore, HPPD herbicides are one of the powerful tools for solving the current problem of concentrated weed resistance.

[0006] CN110963973A discloses a triketone compound containing a quinazolinidone fragment, its preparation method and application, and a herbicide. The compound provided by this prior art has excellent control efficacy against six common grass and broadleaf weeds, namely barnyard grass, foxtail, crabgrass, amaranth, lambsquarters, and velvetleaf. However, the compound provided by this prior art has poor safety for crops such as wheat. Summary of the Invention

[0007] One of the objectives of this invention is to overcome the aforementioned deficiencies in the prior art and provide a novel, ultra-efficient herbicide suitable for grain crop fields.

[0008] The second objective of this invention is to provide a broad-spectrum HPPD herbicide that can be used to control grassy weeds and some broadleaf weeds.

[0009] To achieve the above objectives, a first aspect of the present invention provides a trione-quinazolinedione compound having the structure shown in formula (I).

[0010]

[0011] In equation (I),

[0012] R is selected from -(CH2) n -R 1 C 1-12 Alkyl, C 3-8 cycloalkyl;

[0013] n is 0, 1, 2, or 3;

[0014] R 1 The phenyl group is selected from unsubstituted or substituted with at least one group in combination A;

[0015] Combination A consists of halogen, C 1-6 Alkyl, C 1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl composition.

[0016] A second aspect of the present invention provides a method for preparing the compound described in the first aspect, the method comprising: contacting a compound with the structure shown in formula (II) with a catalyst in the presence of a base and a solvent under rearrangement reaction conditions;

[0017]

[0018] In equation (II), the definition of R is the same as that in the first aspect.

[0019] A third aspect of the invention provides the use of the compounds described in the first aspect in the control of weeds.

[0020] A fourth aspect of the present invention provides a herbicide comprising an active ingredient and excipients, wherein the active ingredient comprises at least one of the compounds described in the first aspect or their agriculturally chemically acceptable salts, hydrates, solvates, or enantiomers or optically active derivatives thereof.

[0021] The aforementioned compounds provided by this invention, or their agriculturally chemically acceptable salts, hydrates, solvates, or their enantiomers and optically active derivatives, possess excellent herbicidal activity.

[0022] The aforementioned compounds provided by this invention, or their agriculturally chemically acceptable salts, hydrates, solvates, or their enantiomers and optically active derivatives, are applicable to weed control in grain crop fields, especially wheat fields.

[0023] In other words, the aforementioned compounds provided by this invention, or their agriculturally chemically acceptable salts, hydrates, solvates, or their enantiomers and optically active derivatives, have excellent safety for crops in grain-type crop fields, especially wheat fields. Detailed Implementation

[0024] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0025] “C 1-12 "Alkyl" refers to a straight-chain or branched alkyl group with a total of 1-12 carbon atoms. For example, the number of carbon atoms can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, and n-hexyl. "C" 1-6 Alkyl groups, etc., have similar definitions.

[0026] “C 3-8 "Cycloalkyl" refers to saturated cycloalkyl groups with 3, 4, 5, 6, 7, or 8 carbon atoms in the ring, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0027] “C 1-6 "Alkoxy" refers to a straight-chain or branched alkoxy group with a total number of carbon atoms of 1-6. For example, the number of carbon atoms can be 1, 2, 3, 4, 5, or 6, including but not limited to methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexyloxy, etc.

[0028] In this invention, "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0029] As previously described, a first aspect of the present invention provides a triketone-quinazolinedione compound having the structure shown in formula (I).

[0030]

[0031] In equation (I),

[0032] R is selected from -(CH2) n -R 1 C 1-12 Alkyl, C 3-8 cycloalkyl;

[0033] n is 0, 1, 2, or 3;

[0034] R 1 The phenyl group is selected from unsubstituted or substituted with at least one group in combination A;

[0035] Combination A consists of halogen, C 1-6 Alkyl, C1-6 Alkyl groups, C substituted with at least one halogen 1-6 Alkyl composition.

[0036] Preferably, in formula (I),

[0037] R is selected from -(CH2) n -R 1 C 1-6 Alkyl, C 3-6 cycloalkyl;

[0038] n is 0, 1, or 2;

[0039] R 1 The phenyl group is selected from unsubstituted or substituted with at least one group in combination A;

[0040] Combination A consists of halogen, C 1-4 Alkyl, C 1-4 Alkyl groups, C substituted with at least one halogen 1-4 Alkyl composition.

[0041] More preferably, in equation (I),

[0042] R is selected from -(CH2) n -R 1 Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, cyclopropyl, cyclobutyl, cyclohexyl;

[0043] n is 0 or 1;

[0044] R 1 The phenyl group is selected from unsubstituted or substituted with at least one group in combination A;

[0045] Combination A consists of fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, and C substituted with at least one halogen. 1-4 Alkyl composition.

[0046] More preferably, in formula (I),

[0047] R is selected from -(CH2) n -R 1 Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, cyclopropyl, cyclobutyl, cyclohexyl;

[0048] n is 0 or 1;

[0049] R 1The phenyl group is selected from unsubstituted or substituted with at least one group in combination A;

[0050] Combination A consists of fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, and trifluoromethyl.

[0051] In particularly preferred cases, the compound with the structure shown in formula (I) is selected from any one of the following:

[0052] Compound 1: Compound 2:

[0053] Compound 3: Compound 4:

[0054] Compound 5: Compound 6:

[0055] Compound 7: Compound 8:

[0056] Compound 9: Compound 10:

[0057] Compound 11: Compound 12:

[0058] Compound 13: Compound 14:

[0059] Compound 15: Compound 16:

[0060] Compound 17: Compound 18:

[0061] Compound 19: Compound 20:

[0062] Compound 21:

[0063] The above-mentioned triketone-quinazolindione compounds provided by this invention can be used as broad-spectrum HPPD herbicides for controlling grassy weeds and some broadleaf weeds. Furthermore, the above-mentioned compounds provided by this invention have good control efficacy against a variety of difficult-to-control weeds, including shepherd's purse, lambsquarters, lambskin, velvetleaf, cleavers, speedwell, chickweed, ironweed, black nightshade, lantern grass, purslane, amaranth, carp intestines, barnyard grass, goosegrass, golden foxtail, foxtail grass, crabgrass, wild oats, Japanese wild oats, jointed goatgrass, wild oats, wild oats, barnyard grass, double-spike barnyard grass, fireweed, and sedge.

[0064] The present invention does not particularly limit the specific method for obtaining the above-mentioned triketone-quinazoline dione compounds. Those skilled in the art can obtain a suitable method for preparing triketone-quinazoline dione compounds by combining the specific structure of the triketone-quinazoline dione compounds provided by the present invention with the synthesis methods in the field of organic synthesis.

[0065] However, in order to improve the yield of the obtained triketone-quinazolinedione compounds, as mentioned above, the second aspect of the present invention provides a method for preparing the compounds described in the first aspect, the method comprising: contacting a compound with the structure shown in formula (II) with a catalyst in the presence of a base and a solvent under rearrangement reaction conditions;

[0066]

[0067] In equation (II), the definition of R is the same as that in the first aspect.

[0068] According to the method for preparing compounds of formula (I) of the present invention, those skilled in the art can contact compounds of formula (II) with catalysts in the presence of base and solvent according to conventional conditions and operations of rearrangement reactions.

[0069] In a preferred embodiment, the molar ratio of the compound with the structure shown in formula (II) to the catalyst and the base is 1:(0.01-1):(0.5-4); more preferably, the molar ratio of the compound with the structure shown in formula (II) to the catalyst and the base is 1:(0.05-1):(1-3).

[0070] In a preferred embodiment, the contact conditions include: a reaction temperature of 0-100°C and a reaction time of 0.5-24 h; more preferably, the contact conditions include: a reaction temperature of 20-40°C and a reaction time of 5-12 h.

[0071] Those skilled in the art should understand that the method described in this invention may also include a step of purifying the obtained product. There are no special requirements for the purification method, and various purification methods commonly used by those skilled in the art can be adopted. For example, extraction with an extractant, drying with a drying agent, and removal of impurities by column chromatography or other methods can be used.

[0072] In the preparation method described in this invention, the compound with the structure shown in formula (II) can be commercially available or prepared by conventional reactions in the art.

[0073] For example, compounds with the structure shown in formula (II) can be prepared using the synthetic route shown below:

[0074]

[0075] Specifically, in the presence of glacial acetic acid, compound I-1 is reacted with iodine monochloride to obtain compound I-2, which is further reacted with isocyanates of different substitutions (R-NCO) to obtain intermediate compound-3. Then, in the presence of N,N-dimethylformamide (DMF) and cesium carbonate, intermediate compound-3 is reacted with iodomethane to obtain intermediate compound-4. Further, intermediate compound-4 is mixed sequentially with 1,3-cyclohexanedione, 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene (Xantphos), palladium chloride and potassium carbonate. Under a CO atmosphere, ultra-dry acetonitrile (MeCN) and triethylamine (Et3N) are added sequentially to react and obtain the compound with the structure shown in formula (II).

[0076] In a preferred embodiment, the catalyst is selected from at least one of sodium cyanide, potassium cyanide, acetone cyanohydrin, trimethylcyanosilane, 1,2,4-triazole and benzo-1,2,4-triazole.

[0077] Preferably, the alkali is selected from at least one of potassium carbonate, sodium carbonate, cesium carbonate, triethylamine, and pyridine.

[0078] Preferably, the solvent is selected from at least one of dichloromethane, trichloromethane, dichloroethane, acetonitrile, toluene, tetrahydrofuran, and benzene.

[0079] As previously stated, a third aspect of the present invention provides the use of the compounds described in the first aspect in the control of weeds.

[0080] The weeds described in this invention are plants that grow in areas harmful to human survival and activities, and can be non-cultivated wild plants or plants useless to humans. For example, they can be various wild plants in crop fields.

[0081] Preferably, the weed is at least one weed selected from sorghum fields, soybean fields, rapeseed fields, wheat fields, rice fields, corn fields, and peanut fields; more preferably, the weed is at least one selected from grass weeds and broadleaf weeds. More preferably, the weed is at least one weed selected from wheat fields.

[0082] Preferably, the weeds are selected from at least one of grass weeds and broadleaf weeds.

[0083] Preferably, in the foregoing application of the present invention, the amount of the compound used is 10-400 g / ha.

[0084] In the application of the compound provided by the present invention as described above, the compound is used after being dissolved and diluted with a solvent, and the concentration after dissolution and dilution is preferably 0.05-0.4 g / L. The solvent for dissolving the compound may include N,N-dimethylformamide, dimethyl sulfoxide, etc., and the dilution reagent may be water containing common additives. Preferably, one or more additives commonly used in herbicides in the art, such as surfactants, emulsifiers, etc., may be added to the solution containing the compound. The diluted compound of the present invention can be sprayed onto the stems and / or leaves of plants using conventional methods in the art.

[0085] As previously described, a fourth aspect of the present invention provides a herbicide comprising an active ingredient and excipients, wherein the active ingredient includes at least one of the compounds described in the first aspect of the present invention.

[0086] Preferably, the content of the active ingredient is 1-99.9% by weight. For example, it can be 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, 45 wt%, 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, 90 wt%, 95 wt%, etc.

[0087] The excipients described in this invention are various additives commonly used in the preparation of various formulations of herbicides in the art.

[0088] Preferably, the formulation of the herbicide of the present invention is selected from at least one of emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, mother liquor and mother powder.

[0089] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are commercially available and of analytical grade. Room temperature below refers to 25±3℃.

[0090] Preparation Example 1

[0091]

[0092] 0.6 mol of methyl 2-amino-3-methylbenzoate was placed in a 2 L three-necked round-bottom flask, and 500 mL of glacial acetic acid was added. The mixture was mechanically stirred at room temperature. Simultaneously, 0.7 mol of ICl was dissolved in 300 mL of glacial acetic acid and added to the reaction system using a constant-pressure dropping funnel. After the addition was completed within 30 min, the reaction was continued for 3 h, and the reaction progress was monitored by TCL. After the reaction was completed, the solid was filtered and washed with a small amount of glacial acetic acid, then dried to obtain intermediate I-2, with a yield of 91%.

[0093] 13.7 mmol of intermediate I-2 was weighed and added to a 100 mL Shrek tube. 25 mL of ultradry pyridine was added under a nitrogen atmosphere, followed by stirring and the addition of 17.2 mmol of o-chlorophenyl isocyanate. The mixture was heated to reflux for 10 h, and the reaction progress was monitored by TLC. After the reaction was complete, the system was cooled to room temperature and then poured into 400 mL of ice water. The solid precipitated by stirring was filtered, dried, and intermediate I-3 was obtained in 86% yield.

[0094] In a 100 mL flask, 11.6 mmol of intermediate I-3, 23.2 mmol of cesium carbonate, and 30 mL of DMF were added sequentially. After stirring at room temperature for about 15 min, 34.8 mmol of iodomethane was added, and the reaction was allowed to proceed for about 1 h. The reaction was monitored by TLC. After the reaction was completed, intermediate I-4 was purified by column chromatography with a yield of 81%.

[0095] In a 100 mL Shrek tube, 4 mmol of intermediate I-4, 6 mmol of 1,3-cyclohexanedione, 0.2 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene, 0.2 mmol of palladium chloride, 8 mmol of potassium carbonate, and a magnetic flux were added sequentially. Under a CO atmosphere, 20 mL of ultradry acetonitrile and 8 mmol of triethylamine were added sequentially. After the addition was complete, the reaction system was heated to 80 °C and reacted for 1.5 h. The reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature, and the insoluble matter in the reaction system was filtered. The organic phase was collected, the solvent was evaporated under reduced pressure, and the solution was subjected to column chromatography to obtain intermediate I-5 in 76% yield.

[0096] 3 mmol of intermediate I-5 was weighed and added to a 100 mL round-bottom flask. While stirring, 20 mL of acetonitrile, 6 mmol of triethylamine, and 8 drops of acetone cyanohydrin were added sequentially. The reaction was allowed to proceed overnight at room temperature, and the reaction progress was monitored by TLC. After the starting materials had completely reacted, the solvent was removed, and 20 mL of 1 mol / L hydrochloric acid solution was added to the reaction system. The mixture was then extracted three times with 20 mL of dichloromethane each time. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed. The mixture was then purified by recrystallization from anhydrous methanol to obtain compound 2 in 85% yield.

[0097] Preparation Example 2

[0098]

[0099] 13.7 mmol of intermediate I-2 was placed in a 200 mL round-bottom flask, 50 mL of tetrahydrofuran was added, and 34.3 mmol of ethyl isocyanate was added with stirring. The system was heated to 70 °C and reacted for 48 h. The reaction progress was monitored by TLC. After the starting material was completely reacted, the solvent was removed by vacuum distillation to obtain intermediate I-6 with a yield of 96%.

[0100] In a 100 mL round-bottom flask, 13 mmol of intermediate I-6 and 30 mL of methanol solution were added, followed by the addition of 39 mmol of sodium methoxide under stirring. The reaction was allowed to proceed for approximately 1 h, and the reaction progress was monitored by TLC. After the reaction was complete, the methanol was removed, and 20 mL of 1 mol / L hydrochloric acid solution was slowly added. Subsequently, a large amount of white solid precipitated. This solid was filtered, dried, and the yield of intermediate I-7 was obtained, with a yield of 85%.

[0101] In a 100 mL flask, 11 mmol of intermediate I-7, 22 mmol of cesium carbonate, and 30 mL of DMF were added sequentially. After stirring at room temperature for about 15 min, 33 mmol of iodomethane was added. The reaction was allowed to proceed for about 1 h. The reaction was monitored by TLC. After the reaction was completed, intermediate I-8 was purified by column chromatography with a yield of 84%.

[0102] In a 100 mL Shrek tube, 4 mmol of intermediate I-8, 6 mmol of 1,3-cyclohexanedione, 0.2 mmol of 4,5-bis(diphenylphosphine)-9,9-dimethyloxanthracene, 0.2 mmol of palladium chloride, 8 mmol of potassium carbonate, and a magnetic flux were added sequentially. Under a carbon monoxide atmosphere, 20 mL of ultradry acetonitrile and 8 mmol of triethylamine were added sequentially. After the addition was complete, the reaction system was heated to 80 °C and reacted for 1.5 h. The reaction progress was monitored by TLC. After the reaction was completed, the mixture was cooled to room temperature, and the insoluble matter in the reaction system was filtered. The organic phase was collected, the solvent was evaporated under reduced pressure, and the intermediate I-9 was obtained by column chromatography in 80% yield.

[0103] 3 mmol of intermediate I-9 was weighed and added to a 100 mL round-bottom flask. While stirring, 20 mL of acetonitrile, 6 mmol of triethylamine, and 8 drops of acetone cyanohydrin were added sequentially. The reaction was allowed to proceed overnight at room temperature, and the reaction progress was monitored by TLC. After the starting materials had completely reacted, the solvent was removed, and 20 mL of 1 mol / L hydrochloric acid solution was added to the reaction system. The mixture was then extracted three times with 20 mL of dichloromethane each time. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed. The mixture was then purified by recrystallization from anhydrous methanol to obtain compound 17 in 86% yield.

[0104] The preparation methods of the other compounds of the present invention are the same as those described in the preparation examples above. Table 1 lists the characterization data of some specific compounds of the present invention.

[0105] Table 1

[0106]

[0107]

[0108]

[0109]

[0110]

[0111] Test Example 1

[0112] This test example illustrates the herbicidal activity (expressed as growth inhibition rate (%)) of compounds with the structure shown in formula (I) and comparative compounds.

[0113] Herbicidal activity test (pot method): The test targets are shown in Table 3. Post-emergence foliar spraying: Take a paper cup with an inner diameter of 7 cm, fill it with composite soil (garden soil: seedling substrate, 1:2, v / v) to 3 / 4 full, directly sow weeds, cover with 0.2 cm of soil, and wait until the plants grow to the 4-5 leaf stage for use. The compounds of this invention and comparative compounds D1, D2, D3, and D4 were applied to the plants in an automatic spraying tower at a dosage of 320 g·ai / ha (grams per hectare). After the pesticide solution on the crop leaves dried, the plants were transferred to a greenhouse for cultivation (25°C, 70% humidity). The results were investigated after 30 days.

[0114] The growth inhibition rate was evaluated by visual inspection, and the rating was based on the conditions shown in Table 2. The test results are shown in Table 3.

[0115]

[0116] Table 2

[0117]

[0118]

[0119] Table 3

[0120]

[0121] As shown in Table 3, the compounds provided by this invention have significant inhibitory effects on weeds, including broadleaf and grass weeds. Furthermore, some compounds in this invention exhibited 100% herbicidal efficacy against the five tested weeds at an application rate of 320 g·ai / ha. Therefore, the compounds in this invention have strong prospects for development and commercialization.

[0122] Test Example 2

[0123] The crop safety of the compounds of the present invention was determined using a similar test method and the same evaluation method as in Test Example 1. The difference was that the compounds of the present invention were applied in an automatic spray tower at the dosages shown in Table 4. The test results for weed and crop inhibition are shown in Table 4.

[0124] Table 4

[0125]

[0126] The results shown above demonstrate that the compound provided by this invention has excellent safety for grain crops, particularly wheat.

[0127] Furthermore, the representative compounds of the present invention exhibited excellent crop safety against wheat at doses of 150 g.ai / ha and 120 g.ai / ha. In contrast, the comparative compounds D1, D2, D3, and D4, which have higher herbicidal activity, caused near-total or complete death of wheat at a dose of 150 g.ai / ha. Comparative compounds D1 and D2 severely inhibited wheat growth at a dose of 120 g.ai / ha, and comparative compounds D3 and D4 caused near-total or complete death of wheat at a dose of 120 g.ai / ha.

[0128] In summary, the compounds of this invention can be applied to wheat fields for highly effective control of broadleaf and grassy weeds without causing phytotoxicity. Therefore, this invention is clearly suitable for field application as a selective herbicide for wheat fields and has high commercial value.

[0129] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A trione-quinazolinedione compound, characterized in that, The compound has the structure shown in formula (I). Equation (I); The compounds with the structure shown in formula (I) are selected from any of the following: Compound 2: Compound 11: , Compound 13: Compound 14: Compound 16: .

2. A method for preparing the compound of claim 1, characterized in that, The method includes: contacting a compound with the structure shown in formula (II) with a catalyst in the presence of a base and a solvent under rearrangement reaction conditions; Formula (II); In formula (II), the definition of R corresponds to the corresponding position of the compound shown in claim 1.

3. The method according to claim 2, wherein, The contact conditions include: a reaction temperature of 0-100℃ and a reaction time of 0.5-24h.

4. The method according to claim 2, wherein, The catalyst is selected from at least one of sodium cyanide, potassium cyanide, acetone cyanohydrin, trimethylcyanosilane, 1,2,4-triazole and benzo-1,2,4-triazole.

5. The use of the compound of claim 1 in weed control.

6. The application according to claim 5, wherein, The weeds are selected from at least one type of weed found in sorghum fields, soybean fields, rapeseed fields, wheat fields, rice fields, corn fields, and peanut fields.

7. The application according to claim 6, wherein, The weeds are selected from at least one of grass weeds and broadleaf weeds.

8. The application according to claim 7, wherein, The weeds mentioned are at least one of the following: shepherd's purse, shepherd's purse, lambsquarters, velvetleaf, cleavers, speedwell, chickweed, ironweed, black nightshade, lantern grass, purslane, amaranth, carp intestines, barnyard grass, goosegrass, golden foxtail grass, foxtail grass, crabgrass, wild oats, Japanese wild oats, jointed barnyard grass, wild oats, wild oats, barnyard grass, double-spike barnyard grass, fireweed, and sedge.

9. The application according to any one of claims 5-8, wherein, The amount of the compound used is 10-400 grams per hectare.

10. A herbicide comprising an active ingredient and excipients, said active ingredient comprising the compound of claim 1.

11. The herbicide according to claim 10, wherein, The content of the active ingredient is 1-99.9% by weight.

12. The herbicide according to claim 10 or 11, wherein, The herbicide formulation is selected from at least one of emulsifiable concentrate, suspension concentrate, wettable powder, powder, granule, aqueous solution, mother liquor, and mother powder.

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