A heterocyclic amide-benzimidazolone compound, its preparation method and application, a herbicide and its application

Abstract

The present invention relates to the field of new pesticide compounds, and discloses a heterocyclic amide-benzimidazolone compound, a preparation method and application thereof, a herbicide and an application thereof. The compound has a structure shown in formula (I). The heterocyclic amide-benzimidazolone compound of the present invention has excellent herbicidal activity.

Description

Technical Field

[0001] The present invention relates to the field of new pesticide compounds, and in particular to a heterocyclic amide-benzimidazolone compound, a preparation method and application thereof, a herbicide and an application thereof. Background Art

[0002] The creation and application of highly efficient herbicides are important technical means to ensure food production and maintain national food security.

[0003] In recent years, with the continuous and extensive use of herbicides, the population density and occurrence area of resistant weeds have gradually increased. China is one of the five countries most seriously affected by resistant weeds in the world, and the problem of weed resistance has shown an increasingly serious trend, severely restricting the sustainable development of agricultural production.

[0004] Therefore, the creation of new and highly efficient herbicides to replace traditional herbicides is an urgent need for the integrated control of resistant weeds, the realization of reduction in chemical input and increase in efficiency, and the green and sustainable development of agriculture. Summary of the Invention

[0005] The purpose of the present invention is to provide a herbicide compound with a novel structure and excellent herbicidal activity.

[0006] To achieve the above purpose, in the first aspect of the present invention, a heterocyclic amide-benzimidazolone compound is provided, and this compound has the structure shown in formula (I),

[0007]

[0008] wherein, in formula (I),

[0009] R 11 and R 12 each independently selected from substituted or unsubstituted C1-C 12 alkyl, -SO2-C1-C6 alkyl; and the optional substituents in R 11 and R 12 are selected from halogen, C1-C3 alkoxy, phenyl, phenyl substituted by at least one C1-C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1-C3 alkoxy;

[0010] R2 is H or C1-C3 alkyl;

[0011] X1 is O or -NR x -; R x is C1-C3 alkyl;

[0012] X2 is N or -CR y -; R y is C1-C3 alkyl.

[0013] The second aspect of the present invention provides a method for preparing the compound described in the first aspect, the method comprising: contacting the compound represented by formula (II) with a condensing agent, the compound represented by formula (III), and a basic substance in the presence of a solvent to react;

[0014]

[0015] Wherein, in formula (II) and formula (III), the definitions of each substituent are correspondingly the same as those described in the first aspect.

[0016] The third aspect of the present invention provides the use of the compound described in the first aspect as a herbicide in controlling weeds.

[0017] The fourth aspect of the present invention provides a herbicide, which contains a herbicidally effective amount of an active ingredient, and the active ingredient is at least one of the compounds described in the first aspect.

[0018] The fifth aspect of the present invention provides the use of the compound described in the first aspect or the herbicide described in the fourth aspect in controlling weeds in a field where any one of the crops selected from corn, rice, wheat, sorghum, peanut, soybean, and rapeseed is planted.

[0019] The heterocyclic amide-benzimidazolone compounds provided by the present invention have excellent herbicidal activity and significantly excellent safety for crops.

[0020] Specifically, the heterocyclic amide-benzimidazolone compounds of the present invention have a significant inhibitory effect on weeds including broadleaf weeds, gramineous weeds, and cyperaceous weeds, and have high safety for crops. Detailed Embodiments

[0021] The endpoints and any values disclosed herein are not limited to the exact ranges or values, and these ranges or values should be understood to include values close to these ranges or values. For numerical ranges, between the endpoint values of each range, between the endpoint values of each range and individual point values, and between individual point values, they can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be regarded as specifically disclosed herein.

[0022] “C1-C 12"C1-C12 alkyl" means an alkyl group having 1 to 12 carbon atoms, including straight-chain alkyl groups and branched-chain alkyl groups. For example, it can be a straight-chain alkyl group or a branched-chain alkyl group with a total of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms. For example, it can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, etc. For "C1-C6 alkyl", "C1-C3 alkyl", etc., there are similar explanations, the difference being the number of carbon atoms. And, when there are substituents other than alkyl groups on the "C1-C 12 alkyl", the number of carbon atoms of the existing substituents is not included in the carbon number of the "C1-C 12 alkyl"; for example, when there is a methoxy group as a substituent on the "C 12 alkyl", the total number of carbon atoms of the C 12 alkyl substituted by methoxy is 13.

[0023] "-SO2-C1-C6 alkyl" means that one side of the S atom on the sulfonyl group is connected to the parent nucleus structure, and the other side is connected to a C1-C6 alkyl group.

[0024] "Halogen" means fluorine, chlorine, bromine, or iodine.

[0025] "C1-C3 alkoxy" means methoxy, ethoxy, n-propoxy, or isopropoxy.

[0026] "Phenyl substituted by at least one C1-C3 alkyl" means that the phenyl group is connected to the parent nucleus structure, but there is at least one substituent on the phenyl, and there can also be 2, 3, 4, or 5 substituents. The substituents present on the phenyl are selected from any one or more of C1-C3 alkyls.

[0027] "Phenyl substituted by at least one C1-C3 alkoxy" means that the phenyl group is connected to the parent nucleus structure, but there is at least one substituent on the phenyl, and there can also be 2, 3, 4, or 5 substituents. The substituents present on the phenyl are selected from any one or more of C1-C3 alkoxys.

[0028] "-NR x -" means that the N atom is a ring-forming atom, and there is an R x as a substituent on the N atom.

[0029] "-CR y -" means that the C atom is a ring-forming atom, and there is an R y as a substituent on the C atom.

[0030] As described above, the first aspect of the present invention provides a heterocyclic amide - benzimidazolone compound, which has the structure shown in formula (I).

[0031]

[0032] Wherein, in formula (I),

[0033] R 11 and R 12 each independently selected from substituted or unsubstituted C1 - C 12 alkyl, -SO2 - C1 - C6 alkyl; and the optional substituents in R 11 and R 12 are selected from halogen, C1 - C3 alkoxy, phenyl, phenyl substituted by at least one C1 - C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1 - C3 alkoxy.

[0034] R2 is H or C1 - C3 alkyl.

[0035] X1 is O or -NR x -; R x is C1 - C3 alkyl.

[0036] X2 is N or -CR y -; R y is C1 - C3 alkyl.

[0037] Preferably, R 11 and R 12 each independently selected from substituted or unsubstituted C1 - C8 alkyl, -SO2 - C1 - C6 alkyl; and the optional substituents in R 11 and R 12 are selected from fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n - propoxy, isopropoxy, phenyl, phenyl substituted by at least one C1 - C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1 - C3 alkoxy; more preferably, R 11 is selected from substituted or unsubstituted C1 - C8 alkyl, -SO2 - C1 - C6 alkyl; and the optional substituents in R 11 are selected from fluorine, chlorine, methoxy, ethoxy, n - propoxy, phenyl, phenyl substituted by at least one C1 - C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1 - C3 alkoxy, and R 12 is methyl.

[0038] Preferably, R2 is H, methyl, ethyl, n - propyl or isopropyl; more preferably, R2 is H.

[0039] Preferably, X1 is O or -NR x -; R x is methyl, ethyl, n-propyl or isopropyl; More preferably, X1 is O or -NR x -; R x is methyl, ethyl or n-propyl.

[0040] Preferably, X2 is N or -CR y -; R y is methyl, ethyl, n-propyl or isopropyl; More preferably, X2 is N or -CR y -; R y is methyl, ethyl or n-propyl.

[0041] According to a preferred specific embodiment, in formula (I),

[0042] R 11 and R 12 each independently selected from substituted or unsubstituted C1-C8 alkyl, -SO2-C1-C6 alkyl; and R 11 and R 12 The optional substituents present are selected from fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy, isopropoxy, phenyl, phenyl substituted by at least one C1-C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1-C3 alkoxy;

[0043] R2 is H, methyl, ethyl, n-propyl or isopropyl;

[0044] X1 is O or -NR x -; R x is methyl, ethyl, n-propyl or isopropyl;

[0045] X2 is N or -CR y -; R y is methyl, ethyl, n-propyl or isopropyl.

[0046] According to another preferred specific embodiment, in formula (I),

[0047] R 11 is selected from substituted or unsubstituted C1-C8 alkyl, -SO2-C1-C6 alkyl; and R 11 The optional substituents present are selected from fluorine, chlorine, methoxy, ethoxy, n-propoxy, phenyl, phenyl substituted by at least one C1-C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1-C3 alkoxy;

[0048] R 12 is methyl;

[0049] R2 is H;

[0050] X1 is O or -NR x -; R x is methyl, ethyl or n-propyl;

[0051] X2 is N or -CR y -; R y is methyl, ethyl or n-propyl.

[0052] According to a particularly preferred specific embodiment, the compound of the structure shown in formula (I) is selected from any one of the following:

[0053] Compound 1: Compound 2:

[0054] Compound 3: Compound 4:

[0055] Compound 5: Compound 6:

[0056] Compound 7: Compound 8:

[0057] Compound 9: Compound 10:

[0058] Compound 11: Compound 12:

[0059] Compound 13: Compound 14:

[0060] Compound 15: Compound 16:

[0061] Compound 17: Compound 18:

[0062] Compound 19: Compound 20:

[0063] Compound 21: Compound 22:

[0064] Compound 23: Compound 24:

[0065] Compound 25: Compound 26:

[0066] Compound 27: Compound 28:

[0067] Compound 29: Compound 30:

[0068] Compound 31: Compound 32:

[0069] Compound 33: Compound 34:

[0070] Compound 35: Compound 36:

[0071] The present invention has no particular requirements for the method of preparing the compounds described in the first aspect. Those skilled in the art can determine a suitable synthetic route according to the structural formulas provided by the present invention in combination with the known knowledge in the field of organic synthesis to obtain the compounds described in the first aspect of the present invention. However, in order to achieve significantly higher yields and purities, the present invention provides a preferred method described in the second aspect for preparing the compounds described in the first aspect of the present invention.

[0072] As described 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 represented by formula (II) with a condensing agent, a compound represented by formula (III), and a basic substance in the presence of a solvent for reaction;

[0073]

[0074] Wherein, in formula (II) and formula (III), the definitions of each substituent are correspondingly the same as those described in the first aspect.

[0075] Preferably, the conditions of the contacting include: the reaction temperature is 0-120 °C; the reaction time is 2-24 h.

[0076] Preferably, the solvent is selected from at least one of dichloromethane, chloroform, dichloroethane, acetonitrile, toluene, tetrahydrofuran, and benzene.

[0077] Preferably, the molar ratio of the amount of the compound represented by formula (II) to the amount of the compound represented by formula (III) is 1:0.8-1.5.

[0078] Preferably, the condensing agent is selected from at least one of DCC (dicyclohexylcarbodiimide), DIC (1,3 - diisopropylcarbodiimide), EDCI (1 - (3 - dimethylaminopropyl)-3 - ethylcarbodiimide hydrochloride), CDI (N,N'-carbonyldiimidazole), HATU (O-(7 - azabenzotriazol - 1 - yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), HBTU (O-(benzotriazol - 1 - yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), TBTU (2-(1H - benzotriazol - 1 - yl)-1,1,3,3 - tetramethyluronium tetrafluoroborate), and PyBOP (1H - benzotriazol - 1 - yloxytris(pyrrolidino)phosphonium hexafluorophosphate).

[0079] Preferably, the basic substance is selected from at least one of pyridine, triethylamine, DMAP (4 - dimethylaminopyridine), DIPEA (N,N - diisopropylethylamine), DBU (1,8 - diazabicyclo[5.4.0]undec - 7 - ene), sodium carbonate, potassium carbonate, sodium hydroxide, and potassium hydroxide.

[0080] Without special instructions, the present invention has no special requirements for the dosage ratio relationship of the solvents, condensing agents, and basic substances involved in the foregoing preparation method. Those skilled in the art can adjust it according to the known parameters in the field of organic synthesis, or those skilled in the art can also make reasonable adjustments according to the examples provided in the following text of the present invention to determine.

[0081] In addition, some conventional post - treatments can also be carried out in the synthesis method involved in the second aspect of the present invention, such as filtration, solvent removal, drying, column chromatography, etc. These are well - known to those skilled in the art, and the present invention will not elaborate here. Those skilled in the art should not understand this as a limitation to the present invention.

[0082] As mentioned above, the third aspect of the present invention provides the use of the compound described in the first aspect as a herbicide for controlling weeds.

[0083] Preferably, the weeds are selected from at least one of broad - leaf weeds, gramineous weeds, and cyperaceous weeds.

[0084] Preferably, the weeds are selected from at least one of Descurainia sophia, Capsella bursa - pastoris, Chenopodium album, Abutilon theophrasti, Galium aparine, Veronica didyma, Malachium aquaticum, Acalypha australis, Solanum nigrum, Physalis angulata, Portulaca oleracea, Amaranthus retroflexus, Eclipta prostrata, Echinochloa crusgalli, Eleusine indica, Setaria glauca, Setaria viridis, Digitaria sanguinalis, Alopecurus aequalis, Alopecurus japonicus, Aegilops tauschii, Avena fatua, Bromus japonicus, Leptochloa chinensis, Paspalum distichum, Scirpus juncoides, and Cyperus difformis.

[0085] As described above, the fourth aspect of the present invention provides a herbicide containing an herbicidally effective amount of an active ingredient, which is at least one of the compounds described in the first aspect.

[0086] Preferably, in the herbicide, the content of the active ingredient is 1-100 wt%, 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] Preferably, the herbicide further contains adjuvants.

[0088] The present invention has no special requirements on the types of the adjuvants. Those skilled in the art can select according to the dosage form and in combination with the types of adjuvants known in the pesticide field for application. The present invention will not elaborate herein, and those skilled in the art should not construe it as a limitation to the present invention.

[0089] As described above, the fifth aspect of the present invention provides the use of the compound described in the first aspect or the herbicide described in the fourth aspect in controlling weeds in a field where any one of the crops selected from corn, rice, wheat, sorghum, peanut, soybean, and rapeseed is planted.

[0090] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, the raw materials used are ordinary commercially available analytical pure products.

[0091] Unless otherwise specified, room temperature or normal temperature in the following examples means 25±2°C.

[0092] Preparation Example 1

[0093]

[0094] In a 1L eggplant-shaped flask, add 0.25 mol of 2-chloro-3-nitrobenzoic acid and 600 mL of dichloromethane. Slowly add 0.27 mol of oxalyl chloride and 0.5 mL of DMF under an ice bath. After the addition is complete, transfer the system to room temperature and stir for 4 h. After the reaction is complete, rotary evaporate the solvent, then add 500 mL of methanol to the reaction flask. Monitor the reaction by TLC. After the reaction is complete, remove the solvent and dry to obtain Intermediate II-2 with a yield of 99%.

[0095] Weigh 0.24 mol of intermediate II-2 and add it to a 1 L eggplant-shaped flask. Then add 500 mL of tetrahydrofuran. While stirring, slowly add 1.44 mol of aqueous methylamine solution. React at room temperature and monitor the reaction by TLC. After the reaction is completed, dry the system. Add 500 mL of saturated sodium bicarbonate solution and extract three times with 300 mL of dichloromethane each time. Combine the organic phases, dry and then remove the solvent to obtain intermediate II-3 with a yield of 92%.

[0096] Add 1.11 mol of iron powder, 200 mL of methanol and 94 mL of concentrated hydrochloric acid to a 2 L eggplant-shaped flask. Heat up to 80 °C and react for 30 min. Then dissolve 0.22 mol of intermediate II-3 in 1 L of methanol and add it to the above system. Continue to reflux and react. Monitor the reaction by TLC. After the reaction is completed, filter off the insoluble substances in the system. Remove the solvent from the filtrate by vacuum distillation. Then add 500 mL of water to the system and extract three times with 400 mL of dichloromethane. Collect the organic phase, dry and then remove the solvent to obtain intermediate II-4 with a yield of 93%.

[0097] In a 1 L eggplant-shaped flask, dissolve 0.2 mol of intermediate II-4 in 600 mL of tetrahydrofuran. Then add 0.3 mol of N,N'-carbonyldiimidazole. Heat up to 50 °C and react. Monitor the reaction by TLC. After the reaction is over, remove the solvent. Add 500 mL of water and extract three times with 400 mL of ethyl acetate. Collect the organic phase, dry with anhydrous sodium sulfate and then remove the solvent to obtain the common intermediate II-5 with a yield of 90%.

[0098] Weigh 8 mmol of intermediate II-5 and 16 mmol of cesium carbonate respectively and add them to a 100 mL eggplant-shaped flask. Then add 20 mL of DMF. Stir at room temperature for 30 min and then add 16 mmol of methyl iodide. Monitor the reaction by TLC. If the reaction is completed, pour the system into 60 mL of water and extract three times with 50 mL of ethyl acetate. Collect the organic phase, dry and then purify by column chromatography to obtain intermediate II-6 with a yield of 83%.

[0099] Place 6 mmol of intermediate II-6 in a 100 mL eggplant-shaped flask. Add 16 mL of methanol solution and 8 mL of water. Then weigh 12.00 mmol of LiOH·H2O and add it thereto. Reflux and react. Monitor the reaction by TLC. When the raw materials disappear, remove the methanol in the system. Then add 20 mL of 1 mol / L hydrochloric acid solution under ice bath. A large amount of solid precipitates. Filter by suction and dry to obtain the carboxylic acid intermediate II-7 with a yield of 90%.

[0100] 2 mmol of carboxylic acid intermediate II-7 was added to a 50 mL eggplant-shaped flask, 15 mL of acetonitrile was added and stirred to dissolve, then 2.4 mmol of CDI was added. After refluxing for 1 h, TLC was used for monitoring. After the raw material spot disappeared, 2.4 mmol of 1-methyl-5-aminotetrazole and 4 mmol of DBU were added, and refluxing was continued. The reaction was tracked by TLC. After the reaction was completed, the acetonitrile in the system was dried off, then 20 mL of 1 mol / L hydrochloric acid solution was added, and extraction was carried out 3 times with 20 mL of dichloromethane each time. The organic phases were combined, dried over anhydrous sodium sulfate, the solvent was removed, and recrystallization was carried out with ether to obtain compound 1 with a yield of 70%.

[0101] Preparation Example 2

[0102]

[0103] In a 50 mL eggplant-shaped flask, 2 mmol of carboxylic acid intermediate II-7, 15 mL of acetonitrile and 2.4 mmol of CDI were added respectively. After refluxing for 1 h, TLC was used for monitoring. After the raw material spot disappeared, 2.4 mmol of 2-amino-5-methyl-1,3,4-oxadiazole and 4 mmol of DBU were added, and refluxing was continued. The reaction was tracked by TLC. After the reaction was completed, the solvent was dried off, then 20 mL of 1 mol / L hydrochloric acid solution was added, and extraction was carried out 3 times with 20 mL of dichloromethane each time. The organic phases were combined, dried, the solvent was removed, and recrystallization was carried out with ether to obtain compound 19 with a yield of 67%.

[0104] The preparation methods of the remaining compounds of the present invention refer to the foregoing preparation examples, and the characterization data of the compounds of the present invention are listed in Table 1.

[0105] Some compounds of the present invention were prepared by the method similar to that of Preparation Example 1 and Preparation Example 2, and the characterization data of the obtained compounds are listed in Table 1. The yields in Table 1 are the yields of the last step of the reaction.

[0106] Table 1

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] Test Example 1

[0113] Enzyme level inhibition activity test (coupling method):

[0114] The enzyme-level inhibitory activities of some compounds against Arabidopsis thaliana HPPD (AtHPPD) were tested using the coupling method reported in the literature (Amaya, Alphonso A. et al. Kinetic analysis of human homogentisate 1,2-dioxygenase. Archives of Biochemistry & Biophysics 2004, 421, 135 - 142.). Weigh 2 - 3 mg of the compound into a 1.5 mL EP tube and centrifuge it on a centrifuge for later use. Calculate the volume of the stock solution at 10 mM based on information such as the purity, relative molecular mass, and mass of the inhibitor, and add the corresponding volume of DMSO and mix well. Subsequently, dilute the 10 mM inhibitor solution to 1 mM with DMSO again for later use, and finally dilute the inhibitor to 10 mM with 20 mM HEPES buffer for primary screening. After the primary screening, dilute the inhibitor according to the inhibition rate obtained from the primary screening to prepare 11 concentrations, ensuring a uniform distribution of the inhibition rate of the inhibitor on the enzyme at each concentration. Use the coupling method to test under an enzyme-linked immunosorbent assay reader, perform three parallel tests, and take the average value as the IC 50 value of the inhibitor against AtHPPD, and use the commercial inhibitor mesotrione as a control agent. The results are shown in Table 2.

[0115] Table 2 Evaluation of the enzyme inhibitory activities of some compounds against AtHPPD

[0116] Compound number <![CDATA[IC 50 (μM)]]> Compound number <![CDATA[IC 50 (μM)]]> 1 0.589±0.006 18 0.059±0.002 2 0.351±0.009 23 0.540±0.003 3 0.281±0.001 24 0.638±0.003 4 0.178±0.006 25 0.504±0.008 5 0.057±0.005 26 0.451±0.003 6 0.010±0.006 27 0.592±0.010 7 0.098±0.001 28 0.635±0.008 8 0.060±0.005 29 0.680±0.012 9 0.064±0.006 30 0.582±0.001 10 0.087±0.009 31 0.542±0.008 11 0.076±0.007 32 0.669±0.003 12 0.124±0.006 33 0.585±0.003 13 0.088±0.006 34 0.464±0.004 14 0.075±0.008 35 0.610±0.002 15 0.069±0.001 36 0.676±0.002 16 0.065±0.004 Mesotrione 0.363±0.015 17 0.059±0.003

[0117] Test Example 2

[0118] This test example is used to illustrate the herbicidal activity (expressed as the growth inhibition rate (%)) of the compounds of the present invention.

[0119] Herbicidal activity test (pot method): The test targets are Amaranthus tricolor and Abutilon theophrasti, post-emergence foliar spray: Take a paper cup with an inner diameter of 7 cm, fill it with a composite soil (vegetable garden soil: seedling substrate, 1:2, v / v) to 3 / 4, directly sow weeds, cover the soil with 0.2 cm, and wait until it grows to the 4 - 5 leaf stage for later use. After applying the compounds of the present invention and the aforementioned comparative compounds at a dose of 320 g.ai / ha (grams per hectare) in an automatic spray tower, transfer it to a greenhouse for cultivation (25 °C, humidity 70%) after the liquid medicine on the crop leaves dries, and investigate the results after 30 days.

[0120] The evaluation method for the growth inhibition rate is the visual method, and the rating is specifically carried out according to the situation shown in Table 3. The test results are shown in Table 4.

[0121] Table 3

[0122]

[0123]

[0124] Table 4

[0125]

[0126] As can be seen from the above results, the heterocyclic amide-benzimidazolone compounds provided by the present invention have excellent herbicidal activity.

[0127] 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 technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, including any other suitable combination of each technical feature. These simple modifications and combinations should also be regarded as the content disclosed by the present invention and fall within the protection scope of the present invention.

Claims

1. A heterocyclic amide-benzimidazolone compound, characterized in that, The compound has the structure shown in formula (I), wherein, in formula (I), R 11 and R 12 are each independently selected from substituted or unsubstituted C1-C 12 alkyl, -SO2-C1-C6 alkyl; and the substituents optionally present in R 11 and R 12 are selected from halogen, C1-C3 alkoxy, phenyl, phenyl substituted by at least one C1-C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1-C3 alkoxy; R2 is H or C1-C3 alkyl; X1 is O or -NR x -; R x is an alkyl group having 1 to 3 carbon atoms; X2 is N or -CR y -; R y is an alkyl group having 1 to 3 carbon atoms.

2. The compound according to claim 1, wherein in formula (I), R 11 and R 12 each independently selected from substituted or unsubstituted C1-C8 alkyl, -SO2-C1-C6 alkyl; and R 11 and R 12 optionally present substituents are selected from fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propoxy, isopropoxy, phenyl, phenyl substituted by at least one C1-C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1-C3 alkoxy; R2 is H, methyl, ethyl, n-propyl or isopropyl; X1 is O or -NR x -; R x is methyl, ethyl, n-propyl or isopropyl; X2 is N or -CR y -; R y is methyl, ethyl, n-propyl or isopropyl.

3. The compound according to claim 2, wherein in formula (I), R 11 is selected from substituted or unsubstituted C1-C8 alkyl, -SO2-C1-C6 alkyl; and R 11 The optional substituents present therein are selected from fluorine, chlorine, methoxy, ethoxy, n-propoxy, phenyl, phenyl substituted by at least one C1-C3 alkyl, phenyl substituted by at least one halogen, phenyl substituted by at least one C1-C3 alkoxy; R 12 is methyl; R2 is H; X1 is O or -NR x -; R x is methyl, ethyl or n-propyl; X2 is N or -CR y -; R y is methyl, ethyl or n-propyl.

4. The compound according to claim 3, wherein The compound having the structure shown in formula (I) is selected from any one of the following: Compound 1: Compound 2: Compound 3: Compound 4: Compound 5: Compound 6: Compound 7: Compound 8: Compound 9: Compound 10: Compound 11: Compound 12: Compound 13: Compound 14: Compound 15: Compound 16: Compound 17: Compound 18: Compound 19: Compound 20: Compound 21: Compound 22: Compound 23: Compound 24: Compound 25: Compound 26: Compound 27: Compound 28: Compound 29: Compound 30: Compound 31: Compound 32: Compound 33: Compound 34: Compound 35: Compound 36:

5. A method for preparing the compound according to any one of claims 1-4, characterized in that, The method comprises: in the presence of a solvent, contacting a compound shown in formula (II) with a condensing agent, a compound shown in formula (III), and a basic substance for reaction; wherein, in formula (II) and formula (III), the definitions of each substituent are correspondingly the same as those described in any one of claims 1-4.

6. The method according to claim 5, wherein The conditions of the contacting include: the reaction temperature is 0-120 °C; the reaction time is 2-24 h; and / or The solvent is selected from at least one of dichloromethane, chloroform, dichloroethane, acetonitrile, toluene, tetrahydrofuran and benzene; and / or The molar ratio of the compound shown in formula (II) to the compound shown in formula (III) is 1:0.8-1.

5.

7. Use of the compound according to any one of claims 1-4 as a herbicide for controlling weeds.

8. The application according to claim 7, wherein, The weeds are selected from at least one of broad-leaved weeds, gramineous weeds and cyperaceous weeds; and / or The weeds are selected from at least one of Descurainia sophia, Capsella bursa-pastoris, Chenopodium album, Abutilon theophrasti, Galium aparine, Veronica didyma, Stellaria media, Acalypha australis, Solanum nigrum, Physalis angulata, Portulaca oleracea, Amaranthus retroflexus, Eclipta prostrata, Echinochloa crusgalli, Eleusine indica, Setaria glauca, Setaria viridis, Digitaria sanguinalis, Alopecurus aequalis, Alopecurus japonicus, Aegilops tauschii, Avena fatua, Bromus japonicus, Leptochloa chinensis, Paspalum distichum, Scirpus juncoides, Cyperus difformis.

9. A herbicide, characterized in that, The herbicide contains an active ingredient in an herbicidally effective amount, and the active ingredient is at least one of the compounds described in any one of claims 1-4.

10. Use of the compound according to any one of claims 1-4 or the herbicide according to claim 9 for controlling weeds in a field where any one of the crops selected from maize, rice, wheat, sorghum, peanut, soybean, rapeseed is planted.

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