A compound containing a pyrazole-quinazolinone structure and a herbicide and use

Abstract

The present application relates to the field of pesticide herbicide, disclose a kind of compound containing pyrazole-quinazoline dione structure and a kind of herbicide and application, the compound has the structure shown in formula (I). Pyrazole-quinazoline dione structure compound provided by the present application can be to barnyard grass, euphorbia, crabgrass, dogtail grass, amaranth, goosefoot, abutilon etc. Many kinds of Gramineae weeds and broadleaf weeds that harm the growth of rice have excellent control effect.

Description

Technical Field

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

[0002] p-Hydroxypyruvate dioxygenase (HPPD) is a herbicide target with a unique mechanism of action discovered by researchers in the 1990s. It is a member of the 2histidine-1glutamate triplet oxidase family.

[0003] Within plants, HPPD can catalyze the production of homogentisic acid (HGA) from p-hydroxyphenylpyruvic acid (HPPA), and HGA can further generate plastoquinone and tocopherol, important substances required for photosynthesis in plants.

[0004] However, once the function of HPPD in a plant is inhibited, the plant cannot perform photosynthesis normally, which can lead to bleaching and death.

[0005] Therefore, the development of herbicides targeting HPPD has become a research hotspot for various pesticide companies and research institutes.

[0006] To date, more than a dozen HPPD inhibitors have been developed and marketed for use in field production. Over the past thirty years of widespread application, HPPD herbicides have demonstrated high efficiency, low toxicity, low residue, and high crop safety. Even more encouragingly, these herbicides have a low risk of resistance development, do not cause cross-resistance with other types of herbicides, and exhibit some inhibitory effect on already resistant weeds. This provides strong support for addressing the recent outbreak of herbicide resistance in weeds.

[0007] However, in recent years, most commercially available HPPD herbicides have shown high crop safety only for corn, and have high control effects on common and resistant weeds in corn fields.

[0008] However, for bulk crop fields, such as rice, existing HPPD herbicides cannot fully realize their advantages in controlling resistant weeds in crop fields.

[0009] However, major weeds in rice paddies, such as barnyard grass, amaranth, barnyard grass, foxtail grass, resistant barnyard grass, and Echinochloa crus-galli, have become dominant weeds in resistant populations. This phenomenon has seriously threatened rice, the main food source for more than half of the world's population.

[0010] Currently, existing herbicides for rice paddies are finding it increasingly difficult to control resistant barnyard grass and Echinochloa crus-galli. The continuous development of resistant weeds has seriously affected my country's grain output and poses a significant threat to food security and agricultural economic development.

[0011] Based on this, the creation of a new, highly efficient HPPD inhibitor suitable for rice fields is of great practical significance for controlling resistant weeds and solving the problem of pesticide residues. Summary of the Invention

[0012] The purpose of this invention is to provide a novel, highly effective HPPD inhibitor.

[0013] To achieve the above objectives, a first aspect of the present invention provides a compound containing a pyrazole-quinazolinidone structure, the compound having the structure shown in formula (I):

[0014]

[0015] A second aspect of the present invention provides the use of compounds with the pyrazole-quinazolinedione structure described in the first aspect in the control of weeds.

[0016] A third aspect of the present invention provides a herbicide comprising an active ingredient and excipients, wherein the active ingredient comprises a compound with the pyrazole-quinazolinedione structure described in the first aspect.

[0017] The fourth aspect of the present invention provides the application of the herbicide described in the third aspect in the control of weeds.

[0018] The compounds with the pyrazole-quinazolinedione structure provided by this invention are novel, highly effective HPPD inhibitors.

[0019] The compounds with the pyrazole-quinazolinedione structure provided by this invention have excellent control effects on a variety of grass weeds and broadleaf weeds, including barnyard grass, barnyard grass, crabgrass, foxtail grass, amaranth, lambsquarters, and velvetleaf.

[0020] In addition, the compounds with the pyrazole-quinazolinedione structure provided by this invention are particularly suitable for the control of grass weeds and broadleaf weeds in rice fields.

[0021] Moreover, the compounds of the pyrazole-quinazolinedione structure of the present invention also have high crop safety.

[0022] In particular, the compounds with the pyrazole-quinazolinedione structure provided by this invention have good control efficacy against barnyard grass and Echinochloa crus-galli in paddy fields. Detailed Implementation

[0023] 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.

[0024] As previously stated, a first aspect of the present invention provides a compound containing a pyrazole-quinazolinidone structure, the compound having the structure shown in formula (I):

[0025]

[0026] The present invention does not particularly limit the method for synthesizing the compound containing the pyrazole-quinazolinedione structure shown in formula (I). Those skilled in the art can obtain a suitable method for preparing the compound containing the pyrazole-quinazolinedione structure shown in formula (I) by combining the compound structure provided by the present invention with the synthesis method in the field of chemistry.

[0027] By way of example, the present invention provides a method for preparing the compound containing the pyrazole-quinazolinedione structure shown in formula (I) by comprising the steps described below, the method comprising contacting the compound with the structure shown in intermediate 2 with propargyl bromide in the presence of a base and a solvent under nucleophilic reaction conditions;

[0028] Intermediate 2:

[0029] There are no special requirements for the specific operating parameters involved in the aforementioned preparation method; those skilled in the art can determine them based on known conditions in the field of organic synthesis. The example section of this invention provides a specific condition, which should not be construed as a limitation of the invention.

[0030] As previously stated, a second aspect of the present invention provides the use of compounds with the pyrazole-quinazolinedione structure described in the first aspect in the control of weeds.

[0031] Preferably, the weeds are paddy field weeds.

[0032] In a preferred embodiment, the weeds are at least one of the following: barnyard grass, Echinochloa crus-galli, foxtail grass, crabgrass, jointed barley, wild oats, wild oats, Japanese wild oats, ryegrass, rice grass, cassia, morning glory, cocklebur, sedge, vetch, amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, beggar-ticks, double-spike barnyard grass, rice barnyard grass, water bamboo leaf, wild arrowhead, water plantain, raindrop, dayflower, duckweed, fireweed, and sedge.

[0033] Preferably, the amount of the compound with the pyrazole-quinazolinedione structure is 10-400 g / ha.

[0034] As previously described, a third aspect of the present invention provides a herbicide comprising an active ingredient and excipients, wherein the active ingredient comprises a compound with the pyrazole-quinazolinedione structure described in the first aspect.

[0035] Preferably, the content of the active ingredient is 1-99.9% by weight; more preferably, the content of the active ingredient is 5-95% by weight.

[0036] Preferably, the herbicide is formulated from at least one of emulsifiable concentrate, suspension concentrate, powder, granule and aqueous solution.

[0037] More preferably, the powder is a wettable powder.

[0038] As previously stated, the fourth aspect of the present invention provides the application of the herbicide described in the third aspect in the control of weeds.

[0039] Preferably, the weeds are paddy field weeds.

[0040] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, the raw materials used are all commercially available analytical grade products.

[0041] All room temperatures below are 25±1℃.

[0042] The structural formulas of the compounds used for comparison in the test examples section of this invention are as follows:

[0043]

[0044]

[0045] The preparation methods for the comparative compounds can refer to the synthesis methods mentioned in CN110357860A, only the types of raw materials need to be changed according to the different substituents.

[0046] In addition, the comparison compound D24 is a specific compound disclosed in CN110357860A.

[0047] Characterization data for some of the comparative compounds are listed in Table 1.

[0048] Table 1

[0049]

[0050]

[0051] Preparation Example 1

[0052]

[0053] At room temperature, 500 mmol of compound 5 was added to a 2 L reaction flask, followed by 1 L of glacial acetic acid and stirring to dissolve. Then, 550 mmol of ICl was dissolved in 350 mL of glacial acetic acid and added dropwise to the reaction system over 30 min with stirring. After the addition was complete, the reaction mixture was stirred for approximately 3 h. After the reaction was complete, the reaction solution was filtered, and the resulting solid was washed with 500 mL of glacial acetic acid. The dried solid was compound 6, with a yield of 97%.

[0054] 30 mmol of compound 6 was added to a 100 mL two-necked flask, followed by 60 mL of pyridine. Then, 36 mmol of 3-chlorophenyl isocyanate was slowly added to the system with stirring. The reaction mixture was heated to 100 °C and reacted overnight. After the reaction was complete, pyridine was removed by vacuum distillation. The resulting solid was purified by column chromatography to obtain compound 7, with a yield of 74%.

[0055] 22 mmol of compound 7 was added to a 200 mL single-necked flask, followed by 70 mL of DMF. Then, 44 mmol of Cs₂CO₃ was added with stirring, and the reaction mixture was stirred for approximately 30 min. 33 mmol of iodomethane was slowly added dropwise to the reaction mixture, and the mixture was stirred overnight at room temperature after the addition was complete. After the reaction was complete, 200 mL of water was added to the system, and the reaction mixture was extracted three times with 50 mL of ethyl acetate each time. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to give compound 8 in 98% yield.

[0056] 20 mmol of compound 8 and 30 mmol of CuCN were added to a 200 mL double-necked flask, followed by 60 mL of dry DMF. The mixture was refluxed for 12 h. After the reaction was complete, the DMF was removed by vacuum distillation. After cooling, 100 mL of acetone was added to the reaction flask, and the mixture was stirred vigorously for 20 min. Unreacted CuCN was removed by filtration. The filtrate was mixed and filtered to obtain compound 9, with a yield of 84%.

[0057] 15 mmol of compound 9 was added to a 500 mL reaction flask, along with 75 mL of glacial acetic acid, 75 mL of water, and 75 mL of concentrated sulfuric acid. The mixture was stirred. The temperature was raised to 120 °C and the reaction was carried out for 12 h. After the reaction was completed, the mixture was cooled to room temperature. The reaction mixture was poured into 300 mL of ice water, and then 100 mL of ethyl acetate was added for extraction. The organic layer was collected, and the aqueous layer was extracted four times with 50 mL of ethyl acetate. The organic layers were combined, and then extracted three times with 30 mL of 60% sodium hydroxide solution each time. The aqueous layers were combined, and the aqueous layer was acidified to pH 2 with concentrated hydrochloric acid. After standing, a large amount of solid, compound 10, precipitated, with a yield of 74%.

[0058] 10 mmol of compound 10 was dissolved in 35 mL of dry dichloromethane in a 100 mL single-necked flask. 20 mmol of oxalyl chloride was added dropwise under ice bath conditions, followed by 0.1 mmol of DMF. After reacting at room temperature for two hours, the solvent was removed under reduced pressure to obtain the acyl chloride. 20 mmol of compound 4 (synthesized according to the literature Du, XH; Hinklin, RJ; Houze, JB, et al., C5-Alkyl-2-methylurea-Substituted Pyridines as a New Class of Glucokinase Activators. Acs Med Chem Lett 2014, 5(12), 1284-1289) was dissolved in 10 mL of dry dichloromethane in 25 mL of dry dichloromethane, followed by the addition of 40 mmol of triethylamine. The reaction was then stopped after 30 min at room temperature. The system was washed with 50 mL of saturated sodium bicarbonate solution, extracted with dichloromethane (15 mL × 3), and the organic phases were combined and purified by column chromatography to obtain intermediate 1. The yield was 78%. 1 H NMR (400MHz, CDCl3) δ8.26(d,J=8.8Hz,1H),7.51(d,J=2.4Hz,1H),7.49–7.45(m,2H),7.32–7.27(m,2H),7.18( t,J=6.8Hz,1H),6.29(d,J=2.4Hz,1H),4.12(q,J=7.2Hz,2H),3.69(s,3H),3.07(s,3H),1.46(t,J=7.2Hz,3H).

[0059] Preparation Example 2

[0060] The target compound shown in formula (I) was prepared using intermediate 1, specifically:

[0061] Under N2 protection in a 100 mL two-necked flask, 7 mmol of intermediate 1 was dissolved in 20 mL of dry acetonitrile. 14 mmol of triethylamine was added, followed by 0.01 mmol of acetone cyanohydrin. The reaction was carried out at room temperature for 12 h, and the reaction progress was monitored by TLC until the starting material disappeared. After the reaction was complete, the solvent was removed, the solid was acidified with 20 mL of 1 M HCl, extracted with 10 mL of dichloromethane, the combined organic phases were dried, the solvent was removed under reduced pressure, and recrystallized from 10 mL of methanol to obtain intermediate 2 in 81% yield.

[0062] Intermediate 2:

[0063] In a 100 mL single-necked flask, 5 mmol of intermediate 2 was dissolved in 15 mL of acetonitrile, followed by the addition of 10 mmol of cesium carbonate, and then 10 mmol of propargyl bromide. The mixture was heated to 70 °C, and the reaction was monitored by TLC for 48 h. After the reaction was completed, the target compound, represented by formula (I), was obtained by column chromatography. The yield was 90%.

[0064] Melting point: 171-172℃. 1 H NMR (400MHz, CDCl3) δ7.64(d,J=8.8Hz,1H),7.48–7.43(m,2H),7.30(t,J=2.0Hz,1H),7.28(s,1H),7.22(d,J=8.8Hz,1H),7.19(d, J=7.2Hz,1H),5.33(d,J=2.4Hz,2H),4.14(q,J=7.2Hz,2H),3.67(s,3H),2.75(s,3H),2.55(t,J=2.4Hz,1H),1.46(t,J=7.2Hz,3H).

[0065] Test Example 1

[0066] This test example is used to test the herbicidal activity of compounds with the structure shown in formula (I) and comparative compounds.

[0067] Preliminary screening test (greenhouse pot method):

[0068] A certain amount of the compound was weighed using an analytical balance and dissolved in DMF containing 1% by weight of Tween-80 emulsifier to prepare a stock solution. This stock solution was then diluted with distilled water to different concentrations for later use. Weeds tested are listed in Table 2. For post-emergence foliar spraying, a 7cm inner diameter paper cup was filled with composite soil (garden soil: seedling substrate, 1:2, v / v) to 3 / 4 full. Weeds were directly sown and covered with 0.2cm of soil. The mixture was stored until it reached the 4-5 leaf stage. The compound of this invention (hereinafter referred to as the target compound) and the aforementioned comparative compound were applied at a dosage of 10g·ai / mu (grams per acre) using an automatic spray tower. After the foliar spray dried, the mixture was transferred to a greenhouse for cultivation (25℃, 70% humidity). Results were investigated after 30 days. The herbicidal activity of the compound was evaluated visually. Specific results were rated according to Table 2. The herbicidal activity test results are shown in Table 3.

[0069] Table 2

[0070] 0 It has no effect on the growth of weeds or crops, and there are no symptoms of pesticide efficacy. Level 0 (same as control) 1-19 It has a slight impact on the growth of weeds or crops, with no obvious symptoms of efficacy. Level 1 20-49 It affects the growth of weeds or crops and has obvious medicinal effects. Level 2 50-79 Weeds or crops are severely inhibited in growth Level 3 80-99 Weeds or crops are basically dead Level 4 100 Weeds or crops completely dead Level 5

[0071] Table 3

[0072]

[0073]

[0074] Test Example 2

[0075] The substances shown in Table 4 were re-screened using the same method as in Test Example 1, with the dosage reduced. The herbicidal activity of the compounds was evaluated by visual inspection, and the ratings were performed according to Table 2. The test results are shown in Table 4.

[0076] Table 4

[0077]

[0078]

[0079]

[0080] The results shown above demonstrate that, in the initial screening herbicidal activity test in the greenhouse, the compounds of this invention exhibited excellent herbicidal efficacy against common grasses and broadleaf weeds such as barnyard grass, foxtail grass, crabgrass, amaranth, lamb's quarters, and velvetleaf.

[0081] Compared to the compounds of the present invention, the control effects of comparative compounds D1 to D8 on the tested weeds were all lower than those of the compounds of the present invention, and the differences in control efficacy of each compound against different weeds were quite significant. In particular, comparative compounds D4 and D7 had virtually no control effect on the tested weeds.

[0082] Compared to the compounds of the present invention, the comparative compounds D9 to D18, which incorporate ester substitution, showed comparable or slightly lower activity against the tested weeds at a dose of 10 g·ai / mu. This indirectly demonstrates that the propargyl ether fragment in the compounds of the present invention has a significant promoting effect on enhancing the herbicidal activity of HPPD inhibitors.

[0083] Further analysis and comparison revealed that the herbicidal activities of compounds with H, methyl, ethyl, propyl, and cyclopropyl (D19, D20, D21, D22) introduced at positions 1 and 3 on the left side of the pyrazole, and compound D24 (the specific compound disclosed in CN110357860A), were slightly lower than or equivalent to those of the compounds of this invention. Among them, D24 exhibited the best herbicidal activity, which was close to that of the compounds of this invention.

[0084] In further screening experiments at reduced concentrations, the compounds of this invention exhibited excellent herbicidal activity against barnyard grass, foxtail, and other grassy weeds. Furthermore, even at a reduced dose of 2 g·ai / mu, the compounds of this invention maintained excellent efficacy against the tested weeds. Comparative compounds D1 to D24 showed a significant decrease in herbicidal activity at reduced doses. Only comparative compounds D3, D10, D16, and D24 showed herbicidal activity similar to that of the compounds of this invention at reduced doses.

[0085] In summary, the combination of N-ethylpyrazole compound and propargyl ether fragment plays an important role in improving the herbicidal activity of the HPPD inhibitor of the present invention.

[0086] Test Example 3

[0087] The crop safety of the compounds of the present invention was determined using the same method and evaluation system as in Test Example 1. The crop safety evaluation method of the compounds was visual inspection, and the specific results were rated according to Table 2. The test results of crop inhibition are shown in Table 5.

[0088] Table 5

[0089]

[0090]

[0091] The crop safety evaluation results above show that the compounds of this invention have good crop safety for both indica and japonica rice, especially showing almost no inhibitory effect on japonica rice under the three application methods. Comparative compounds D1 to D23 all exhibit significant harmful effects on rice, and therefore cannot be further developed as green, safe, and selective herbicides. Comparative compound D24 is also less safe for rice than the compounds of this invention. Considering the excellent herbicidal activity against difficult-to-control gramineous weeds in rice paddies, the compounds of this invention are clearly suitable for use as herbicides in rice paddies and have significant commercial development value.

[0092] Furthermore, the compounds of this invention also exhibit high crop safety for corn and wheat, and therefore can also be used in corn and wheat fields to control some grasses and some broadleaf weeds.

[0093] Therefore, the compounds of this invention are very safe for at least one of rice, corn, and wheat, and are particularly effective in controlling noxious weeds in rice paddies. They can be developed into industrial-scale herbicides for rice paddies.

[0094] Test Example 4

[0095] Further testing was conducted on the herbicidal activity of the target compound, targeting various wild-type noxious weeds in paddy fields.

[0096] A certain amount of the compound was weighed using an analytical balance and dissolved in DMF containing 1% by weight of Tween-80 emulsifier to prepare a stock solution. This stock solution was then diluted with distilled water to different concentrations for later use. Greenhouse pot cultivation was used. The tested targets were: Barnyardgrass No. 1 (Hubei Barnyardgrass in net bags), Barnyardgrass No. 2 (Shouxian Barnyardgrass), Barnyardgrass No. 3 (Hanshou Barnyardgrass), and Barnyardgrass No. 4 (Northeast Barnyardgrass). Post-emergence foliar spraying: 7cm inner diameter paper cups were filled with composite soil (garden soil: seedling substrate, 1:2, v / v) to 3 / 4 full. Weeds were directly sown and covered with 0.2cm of soil. The sown weeds were allowed to grow to the 2-tillering stage, 3-leaf stage, and 4-leaf stage for later use. The target compound was applied to the crop using an automatic spray tower at different dosages of 5 g.ai / mu, 10 g.ai / mu, 15 g.ai / mu, and 20 g.ai / mu. After the herbicide solution dried on the crop leaves, the plants were transferred to a greenhouse for cultivation (25-28°C, 70% humidity). The results were collected after 24 days. The herbicidal activity of the compound was evaluated visually, and the specific results are rated according to Table 2. The test results are shown in Tables 6 and 7.

[0097] Table 6

[0098]

[0099] Table 7

[0100]

[0101] The test results above show that the compound of this invention has excellent herbicidal activity against barnyard grass at different leaf stages in different regions, achieving almost complete suppression. Furthermore, the compound of this invention is significantly more effective than the comparative compound D24 in controlling barnyard grass at the 3-leaf, 4-leaf, and 2-tillering stages, making it more beneficial for barnyard grass control in paddy fields.

[0102] Therefore, the compounds of this invention are very safe for rice and exhibit particularly outstanding control effects against noxious weeds in rice paddies. They can be developed into industrial-scale herbicides for rice paddies.

[0103] Test Example 5

[0104] Further testing was conducted on the safety of the compounds of this invention for different rice varieties. A certain amount of the compound was weighed using an analytical balance and dissolved in DMF containing 1% by weight of Tween-80 emulsifier to prepare a stock solution. This stock solution was then diluted with distilled water to different concentrations for later use. The test targets were indica rice varieties: Taifeng, Wanmeixiang, and Zhaoxiang No. 1, and japonica rice. A greenhouse pot cultivation method was used, with post-emergence foliar spraying: 7cm inner diameter paper cups were filled with composite soil (garden soil: seedling substrate, 1:2, v / v) to 3 / 4 full, and the crops were directly sown, covered with 0.2cm of soil. Samples were taken at the two tillering stages and at the 4-5 leaf stage for later use. The compound was applied at different dosages (5g.ai / mu, 10g.ai / mu, 15g.ai / mu, 20g.ai / mu) using an automatic spray tower. After the pesticide solution on the crop leaves dried, the plants were transferred to a greenhouse for cultivation (25℃-28℃, 70% humidity). Results were collected after 24 days. The herbicidal activity of the compounds was evaluated by visual inspection. The specific results were rated according to Table 2, and the test results are shown in Table 8.

[0105] Table 8

[0106]

[0107] The test results above show that the compound of the present invention exhibits excellent crop safety for different rice varieties, and is more effective in protecting rice than the comparative compound D24, thus having broad application and development prospects.

[0108] Test Example 6

[0109] Field trials were conducted on the compounds of this invention. The experimental location was Sanya, Hainan Province, and the test crops were indica rice and japonica rice. The test weeds were barnyard grass (Echinochloa crus-galli), 4-leaf stage barnyard grass, and 2-tillering stage barnyard grass. Test method: 20m 2 Each treatment was repeated three times in one plot. Foliar spraying was applied 12 days after direct seeding of rice, followed by irrigation 48 hours later, with water retention for 5-7 days. Twenty days after treatment, the treated and control areas were visually observed to assess weed control efficacy and crop safety. The herbicidal activity of the compounds was evaluated visually, and the specific results are rated according to Table 2. The test results are shown in Table 9.

[0110] Table 9

[0111]

[0112] The results of the above field trials show that, at a dosage of 5 g / mu, the compound of the present invention has good crop safety for rice. Furthermore, even with increased dosage, rice only exhibits mild symptoms without affecting normal growth, and there is no phytotoxicity. It is also effective in controlling barnyard grass and other weeds in rice paddies.

[0113] In summary, the compounds of this invention can be used as HPPD herbicides in paddy fields, which helps to control noxious weeds in paddy fields.

[0114] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A compound containing a pyrazole-quinazolinedione structure, characterized in that, The compound has the structure shown in formula (I): Equation (I).

2. The application of the compound with the pyrazole-quinazolinedione structure according to claim 1 in the control of weeds.

3. The application according to claim 2, wherein, The weeds mentioned are rice paddy weeds.

4. The application according to claim 2, wherein, The weeds mentioned are at least one of the following: barnyard grass, Echinochloa crus-galli, foxtail grass, crabgrass, jointed barley, wild oats, wild oats, wild wheatgrass, ryegrass, rice grass, cassia, morning glory, cocklebur, sedge, vetch, amaranth, false groundcherry, angelica sinensis, purslane, spiny amaranth, beggar-ticks, double-spike barnyard grass, rice barnyard grass, water bamboo leaf, wild arrowhead, water plantain, raindrop, dayflower, duckweed, and fireweed.

5. The application according to claim 2, wherein, The weeds mentioned are at least one of Japanese wild oats and Cyperus difformis.

6. The application according to any one of claims 2-5, wherein, The amount of the compound with the pyrazole-quinazolinidone structure used is 10-400 g / ha.

7. A herbicide comprising an active ingredient and excipients, said active ingredient comprising a compound with the structure of pyrazole-quinazolinidone as described in claim 1.

8. The herbicide according to claim 7, wherein, The content of the active ingredient is 1-99.9% by weight.

9. The herbicide according to claim 8, wherein the content of the active ingredient is 5-95% by weight.

10. The herbicide according to claim 7 or 8, wherein, The herbicide formulation is selected from at least one of emulsifiable concentrate, suspension concentrate, powder, granule and aqueous solution.

11. The herbicide according to claim 10, wherein, The powder is a wettable powder.

12. The use of the herbicide according to any one of claims 7-11 in the control of weeds.

13. The application according to claim 12, wherein the weeds are paddy field weeds.

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