A benzoylpyrazole compound and its application

Abstract

The present invention discloses a benzoylpyrazole compound and its application. The compound is represented by the general formula (I): #imgabs0#. The definitions of the substituents in the general formula I are as described in the specification. The compound of the general formula I of the present invention has excellent herbicidal activity and can be used to control agricultural weeds.

Description

Technical Field

[0001] The present invention belongs to the field of herbicides, and specifically relates to a benzoylpyrazole compound and its application. Background Art

[0002] Due to the succession and transformation of weed populations, as well as the emergence and rapid development of resistance to chemical pesticides, people are increasingly aware of ecological and environmental protection, and are increasingly concerned about chemical pesticide pollution, the impact of pesticides on non-target organisms, and the fate of pesticides in the ecological environment. The gradual reduction in the world's arable land area, the continuous growth of the population, and the increasing demand for food are forcing people to rapidly develop agricultural production technologies, improve and perfect farming systems, and continuously invent new and improved herbicidal compounds and compositions.

[0003] CN108264484A reported that benzoylpyrazole compounds have herbicidal activity, such as compound E-33 (KC1) and compound E-49 (KC2):

[0004]

[0005] J.Pestic.Sci.46(2),152–159(2021) reported that benzoylpyrazole compounds have herbicidal activity, such as compound No. 30 (KC3).

[0006]

[0007] Benzoylpyrazole compounds as shown in the present invention have not been disclosed. Summary of the Invention

[0008] The present invention aims to provide a benzoylpyrazole compound which is novel in structure and safe for crops and its application.

[0009] To achieve the above object, the technical solution of the present invention is as follows:

[0010] A benzoylpyrazole compound, the compound is shown in general formula I:

[0011]

[0012] Where:

[0013] R1 is selected from halogen or C1-C6 alkyl;

[0014] R2 is selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 halocycloalkylC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkoxy, C1-C6 haloalkoxyC1-C6 alkyl, C1-C6 haloalkoxyC1-C6 alkoxy, C1-C6 alkoxyC1-C6 alkoxy, C3-C6 cycloalkylC1-C3 alkoxy, C3-C6 cycloalkyloxy, C1-C6 alkoxyC1-C6 alkoxyC1-C6 alkyl or C1-C6 alkoxyC1-C6 alkoxyC1-C6 alkoxy.

[0015] R3 is selected from C1-C6 alkyl;

[0016] R4 is selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0017] R5 is selected from H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 halocycloalkylC1-C3 alkyl, C1-C6 alkoxy, C2-C6 alkenyl or C2-C6 alkynyl.

[0018] When R1 is selected from methyl, R5 is selected from H, R2 is not

[0019] The further preferred compound is, in the general formula I:

[0020] R1 is selected from halogen or C1-C6 alkyl;

[0021] R2 is selected from halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 halocycloalkylC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl or C1-C6 alkoxyC1-C6 alkoxy

[0022] R3 is selected from C1-C6 alkyl;

[0023] R4 is selected from C1-C6 alkyl or C1-C6 haloalkyl;

[0024] R5 is selected from H, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 halocycloalkylC1-C3 alkyl, C1-C6 alkoxy, C2-C6 alkenyl or C2-C6 alkynyl.

[0025] When R1 is selected from methyl, R5 is selected from H, R2 is not

[0026] The further preferred compound is, wherein:

[0027] R1 is selected from F, Cl, Br or C1-C3 alkyl;

[0028] R2 is selected from C1-C3 alkoxy, C1-C3 alkoxy C1-C3 alkyl or C1-C3 alkoxy C1-C3 alkoxy

[0029] R3 is selected from C1-C3 alkyl;

[0030] R4 is selected from C1-C3 alkyl;

[0031] R5 is selected from H, C1-C3 alkyl, C1-C3 haloalkyl or C3-C6 cycloalkyl.

[0032] When R5 is selected from H, R1 is selected from methyl, R2 is not

[0033] The further preferred compound is, wherein:

[0034] R1 is selected from Cl, Br, methyl, ethyl, n-propyl or isopropyl;

[0035] R2 is selected from methoxymethyl, methoxyethoxy or propoxy

[0036] R3 is selected from methyl, ethyl, n-propyl or isopropyl;

[0037] R4 is selected from methyl, ethyl, n-propyl or isopropyl;

[0038] R5 is selected from H, methyl, ethyl, n-propyl or isopropyl, trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl or cyclopropyl.

[0039] When R1 is selected from methyl, R5 is selected from H, R2 is not

[0040] In the definition of compounds of general formula I given above, the terms used are collectively defined as follows:

[0041] Alkyl refers to a linear or branched chain, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, and n-hexyl. Cycloalkyl refers to a cyclic chain, such as cyclopropyl, methylcyclopropyl, cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Alkoxy refers to an alkyl group with an oxygen atom attached to the end, such as methoxy, ethoxy, n-propoxy, isopropoxy, and tert-butoxy.

[0042] The general formula compound I of the present invention can be prepared by the following method:

[0043]

[0044] The compound of formula II is reacted with the compound of formula III (commercially available) in a suitable solvent at a temperature of -10°C to the boiling point of the suitable solvent for 0.5-48 hours to obtain the target compound I.

[0045] Suitable solvents are selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide or dimethyl sulfoxide.

[0046] The addition of a suitable base is beneficial to the reaction. Suitable bases are selected from organic bases such as triethylamine, N,N-dimethylaniline or pyridine, or inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide.

[0047] The preparation method of the compound of formula II is as follows:

[0048]

[0049] In the above formula, the compound of formula IV is reacted in the presence of a base and a catalyst in a suitable solvent at a temperature of -10°C to the boiling point of the suitable solvent for 0.5-48 hours to obtain the compound of formula II. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide, or dimethyl sulfoxide. The suitable base is selected from sodium carbonate, potassium carbonate, or triethylamine. The suitable catalyst is selected from sodium carbonate, potassium carbonate, acetone cyanohydrin, azide, quaternary ammonium azide, metal cyanide, or DMAP.

[0050] The preparation method of the compound of formula IV is as follows:

[0051]

[0052] The compound of formula V is reacted with a compound of formula VI (available commercially or prepared by the method described in EP0240001) in a suitable solvent at a temperature of -10°C to the boiling point of the suitable solvent for 0.5-24 hours to obtain a compound of formula IV. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N,N-dimethylformamide, or dimethyl sulfoxide.

[0053] The addition of a suitable base is beneficial to the reaction. Suitable bases are selected from organic bases such as triethylamine, N,N-dimethylaniline or pyridine, or inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide.

[0054] The corresponding carboxylic acid (prepared as described in CN101573035A) of the raw material for the compound of formula V is reacted with an acyl halide reagent in a suitable solvent at a temperature between -10°C and the boiling point of the suitable solvent for 0.5-48 hours to prepare the compound of formula V. The acyl halide reagent is selected from oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus trichloride, or phosphorus pentachloride. The suitable solvent is selected from dichloromethane, 1,2-dichloroethane, hexane, benzene, toluene, acetonitrile, acetic acid, dioxane, or a liquid acyl halide reagent.

[0055] The compounds of the general formula I of the present invention have herbicidal activity and can be used to control various weeds in agriculture. Compared with the compounds disclosed in the prior art, the benzoylpyrazole compounds of the present invention not only have excellent herbicidal activity but are also safe for crops.

[0056] The present invention also includes a herbicidal composition containing the compound of formula I as an active ingredient. The weight percentage of the active ingredient in the herbicidal composition is 1-99%. The herbicidal composition also includes an agriculturally acceptable carrier.

[0057] The herbicidal compositions of the present invention can be applied in a variety of formulations. Typically, the compounds of the present invention are dissolved or dispersed in a carrier to prepare formulations that facilitate their dispersibility when used as herbicides. For example, these chemical formulations can be formulated as wettable powders or emulsifiable concentrates. Therefore, these compositions require at least one liquid or solid carrier and typically require the addition of a suitable surfactant.

[0058] The present invention also provides a method for controlling weeds, comprising applying a herbicidally effective amount of the herbicidal composition of the present invention to the weeds, the locus where the weeds grow, or the surface of the growth medium thereof. A preferred effective dose is 1 to 1000 grams per hectare, with a preferred effective dose being 10 to 500 grams per hectare. For certain applications, one or more other herbicides may be added to the herbicidal composition of the present invention to provide additional advantages and effects.

[0059] The compounds of the present invention can be used alone or in combination with other known insecticides, fungicides, plant growth regulators or fertilizers.

[0060] It should be understood that various changes and modifications can be made within the scope of the present invention as defined by the claims.

[0061] The advantages of the present invention are:

[0062] Compared with known benzoylpyrazole compounds, the general formula compound of the present invention contains a benzoyl group and a pyrazoloyl group as substitutions and has a novel structure. In addition, the benzoylpyrazole compound of the present invention has unexpectedly high herbicidal activity, even at a lower dosage. It is not only highly effective, but also reduces the amount of pesticide used, reduces costs, and reduces pollution to the environment. DETAILED DESCRIPTION

[0063] The following examples and biological test results can be used to further illustrate the present invention, but are not intended to limit the present invention.

[0064] Synthesis Example

[0065] Example 1. Synthesis of Compound 1-158

[0066] (1) Synthesis of 2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoyl chloride

[0067]

[0068] To the reaction flask were added 2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoic acid (1.1 g, 3.8 mmol, obtained by reference to CN101573035A) and toluene (20 ml), and thionyl chloride (2.4 g, 19.1 mmol) was slowly added. The mixture was heated under reflux for 4 h, and the solvent was evaporated under reduced pressure to obtain 1.2 g of a yellow oil, which was used directly in the next step.

[0069] (2) Synthesis of 2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoyl-1,3-dimethyl-5-hydroxypyrazole ester

[0070]

[0071] To a reaction flask, 1,3-dimethyl-5-hydroxypyrazole (0.43 g, 3.8 mmol), 1,2-dichloroethane (20 ml), and triethylamine (0.43 g, 4.2 mmol) were added dropwise, followed by a 1,2-dichloroethane solution (10 ml) of 2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoyl chloride. The mixture was stirred at room temperature for 2 hours. The organic phase was washed once with water (20 ml), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was separated by column chromatography to obtain 1.2 g of a yellow oil, with a yield of 80%.

[0072] (3) Synthesis of 4-(2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoyl)-1,3-dimethyl-5-hydroxypyrazole

[0073]

[0074] To the reaction flask were added 2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoyl-1,3-dimethyl-5-hydroxypyrazole ester (1.2 g, 3.1 mmol), 1,2-dichloroethane (20 ml), triethylamine (0.48 g, 4.7 mmol), and 2 drops of acetone cyanohydrin. The mixture was stirred at room temperature overnight. Water (50 ml) was added and stirred for half an hour. The aqueous phase was adjusted to pH 2-3 with 10% dilute hydrochloric acid and extracted twice with dichloromethane (50 ml * 2). The combined organic phases were washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.1 g of a yellow oil with a yield of 91%.

[0075] (4) Synthesis of Compound 1-158

[0076]

[0077] To a reaction flask were added 4-(2-methyl-3-methoxyethoxy-4-methylsulfonylbenzoyl)-1,3-dimethyl-5-hydroxypyrazole (1.1 g, 2.9 mmol), dichloromethane (20 ml), and triethylamine (0.44 g, 4.4 mmol), followed by the dropwise addition of acetyl chloride (0.35 g, 4.4 mmol). The mixture was stirred at room temperature for 1 hour, and the solvent was evaporated under reduced pressure. The residue was then separated by addition of ethyl acetate (100 ml) and water (50 ml). The organic phase was washed sequentially with saturated brine (50 ml), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography to yield 0.28 g of a yellow oil with a purity of 90%.

[0078] Other compounds of general formula I can be obtained by replacing the starting materials according to the above-described method. Some compounds of general formula I are shown in Table 1.

[0079]

[0080] Table 1 Structures and physical properties of some compounds of formula I

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] Some compounds 1 H NMR (300 MHz, CDCl3) data are as follows:

[0096] Compound 1-2: 1 H NMR (600MHz, DMSO-d6) δ8.00(d,J=8.1Hz,1H),7.62(d,J=8.0Hz,1H),7.32(s,1H),4.92(s,2H),3.49(s,3H),3.36(s,3H),3.31(s,3H),1.87(s,3H).

[0097] Compounds 1-8: 1 H NMR(600MHz,Chloroform-d)δ8.13(d,J=8.1Hz,1H),7.37(d,J=8.1Hz,1H),5.09( s,2H),3.57(s,3H),3.50(s,3H),3.25(s,3H),2.77(q,J=7.5Hz,2H),1.82(s,3H).

[0098] Compounds 1-10: 1 H NMR(600MHz,Chloroform-d)δ8.13(d,J=8.0Hz,1H),7.37(d,J=8.0Hz,1H),5.09(s,2H),3.55 (s,3H),3.50(s,3H),3.44(p,J=6.9Hz,1H),3.25(s,3H),1.73(s,3H),1.28(d,J=6.9Hz,6H).

[0099] Compound 1-11: 1H NMR(600MHz,Chloroform-d)δ8.13(d,J=8.1Hz,1H),7.42(d,J=8.0Hz,1H),5.09(s,2H),3.54( s,3H),3.50(s,3H),3.25(s,3H),2.00(s,3H),0.89(dq,J=5.0,4.0Hz,2H),0.78–0.70(m,2H).

[0100] Compound 1-12: 1 H NMR (600MHz, Chloroform-d) δ 8.14 (d, J = 8.1 Hz, 1H), 7.43 (d, J = 8.1 Hz, 1H), 5.09 (s, 2H), 3.72 (s, 3H), 3.49 (s, 3H), 3.26 (s, 3H), 1.99 (s, 3H).

[0101] Compound 1-13: 1 H NMR(600MHz,Chloroform-d)δ8.14(d,J=8.0Hz,1H),7.41(d,J=8.0Hz,1H),6.93(t ,J=53.7Hz,1H),5.09(s,2H),3.68(s,3H),3.50(s,3H),3.25(s,3H),1.88(s,3H).

[0102] Compound 1-19: 1 H NMR (600MHz, DMSO-d6) δ7.97(d,J=8.1Hz,1H),7.51(d,J=8.1Hz,1H),4.92(s,2H),3.72(q ,J=7.2Hz,2H),3.54(s,3H),3.50(s,3H),3.30(s,3H),1.99(s,3H),1.15(t,J=7.1Hz,3H).

[0103] Compound 1-30: 1 H NMR(600MHz,Chloroform-d)δ8.17(d,J=8.0Hz,1H),7.45(d,J=8.1Hz,1H),4.92(s,2H),4.54 (p,J=6.7Hz,1H),3.55(s,3H),3.50(s,3H),3.27(s,3H),1.71(s,3H),1.47(d,J=6.7Hz,6H).

[0104] Compound 1-158: 1H NMR(600MHz,Chloroform-d)δ7.88(d,J=8.0Hz,1H),7.12(d,J=8.0Hz,1H),4.24–4.18(m,2H),3 .82–3.79(m,2H),3.57(s,3H),3.45(s,3H),3.28(s,3H),2.24(s,3H),2.23(s,3H),1.87(s,3H).

[0105] Compound 1-159: 1 H NMR(600MHz,Chloroform-d)δ7.88(d,J=8.0Hz,1H),7.13(d,J=8.0Hz,1H),4.26–4.19(m,2H),3.82–3.77(m,2H) ,3.57(s,3H),3.46(s,3H),3.28(s,3H),2.76(q,J=7.5Hz,2H),2.25(s,3H),1.79(s,3H),1.21(t,J=7.4Hz,3H).

[0106] Compound 1-161: 1 H NMR(600MHz,Chloroform-d)δ7.88(d,J=8.0Hz,1H),7.13(d,J=8.0Hz,1H),4.25–4.20(m,2H),3.80(m,2H ),3.55(s,3H),3.48(s,3H),3.44–3.37(m,1H),3.30(s,3H),2.25(s,3H),1.77(s,3H),1.31–1.25(m,6H).

[0107] Compound 1-162: 1 H NMR(600MHz,Chloroform-d)δ7.88(d,J=7.9Hz,1H),7.19(d,J=8.0Hz,1H),4.25–4.20(m,2H),3.82–3.78(m,2H),3.54 (s,3H),3.46(s,3H),3.28(s,3H),2.29(s,3H),1.96–2.00(m,1H),1.95(s,3H),0.89–0.91(m,2H),0.81–0.74(m,2H).

[0108] Compound 1-163: 1H NMR(600MHz,Chloroform-d)δ7.88(d,J=8.0Hz,1H),7.21(d,J=8.0Hz,1H),4.23–4.21(m, 2H),3.82–3.79(m,2H),3.74(s,3H),3.46(s,3H),3.29(s,3H),2.30(s,3H),1.99(s,3H).

[0109] Compound 1-164: 1 H NMR(600MHz,Chloroform-d)δ7.90(d,J=8.0Hz,1H),7.18(d,J=8.0Hz,1H),6.89(t,J=53.9Hz,1H),4. 25–4.20(m,2H),3.83–3.78(m,2H),3.70(s,3H),3.46(s,3H),3.29(s,3H),2.28(s,3H),1.88(s,3H).

[0110] Compound 1-170: 1 H NMR(600MHz,Chloroform-d)δ7.89(dd,J=8.0,0.7Hz,1H),7.14(d,J=8.0Hz,1H),4.25–4.19(m,2H),3.88(q,J=7.3 Hz,2H),3.82–3.77(m,2H),3.46(s,3H),3.29(s,3H),2.26(s,3H),2.25(s,3H),1.90(s,3H),1.38(t,J=7.3Hz,3H).

[0111] Compound 1-203: 1 H NMR(600MHz,Chloroform-d)δ7.87(dd,J=8.0,0.7Hz,1H),7.12(d,J=8.0Hz,1H),4.26–4.17(m,2H),3.85–3.76(m, 2H), 3.58 (s, 3H), 3.46 (s, 3H), 3.28 (s, 3H), 2.27 (s, 3H), 2.26 (s, 3H), 2.14 (q, J = 7.5Hz, 2H), 1.05 (t, J = 7.5Hz, 3H).

[0112] Compound 1-225: 1H NMR(600MHz,Chloroform-d)δ7.84(dd,J=8.0,0.7Hz,1H),7.10(d,J=8.0Hz,1H),4.21–4.18(m,2H),3.80–3.76(m,2H),3.55(s ,3H),3.44(s,3H),3.26(s,3H),2.24(s,3H),2.23(s,3H),2.06(t,J=7.5Hz,2H),1.52(q,J=7.4Hz,2H),0.90(t,J=7.4Hz,3H).

[0113] Compound 1-226: 1 H NMR(600MHz,Chloroform-d)δ7.86(dd,J=8.0,0.7Hz,1H),7.13(d,J=8.0Hz,1H),4.26–4.20(m,2H),3.83–3.76(m ,2H),3.57(s,3H),3.46(s,3H),3.27(s,3H),2.38–2.32(m,1H),2.29(s,3H),2.22(s,3H),1.11(d,J=7.0Hz,6H).

[0114] Compound 1-230: 1 H NMR(600MHz,Chloroform-d)δ7.85(dd,J=8.0,0.7Hz,1H),7.15(d,J=8.0Hz,1H),4.23–4.18(m,2H) ,3.82–3.77(m,2H),3.58(s,3H),3.46(s,3H),3.26(s,3H),2.30(s,3H),2.17(s,3H),1.13(s,9H).

[0115] Compound 1-231: 1 H NMR(600MHz,Chloroform-d)δ7.84(dd,J=8.0,0.7Hz,1H),7.15(d,J=8.0Hz,1H),4.23–4.19(m,2H),3.81 –3.76(m,2H),3.58(s,3H),3.45(s,3H),3.30(s,3H),2.79(s,3H),2.62(s,3H),2.36(s,3H),2.28(s,3H).

[0116] Compound 1-232: 1H NMR(600MHz,Chloroform-d)δ7.91(dd,J=8.0,0.8Hz,1H),7.35–7.27(m,3H),7.20–7.14(m,3H),4.2 4–4.20(m,2H),3.82–3.77(m,2H),3.46(s,3H),3.38(s,3H),3.26(s,3H),2.27(s,3H),2.21(s,3H).

[0117] Compound 1-243: 1 H NMR(600MHz,Chloroform-d)δ7.93(d,J=7.8Hz,1H),7.16(d,J=7.9Hz,1H),4.28–4.22(m,2H),3.86–3.82(m,2H) ,3.69(s,3H),3.61(q,J=7.0Hz,2H),3.36(s,3H),3.30(s,3H),2.32(s,3H),1.73(s,3H),1.25(t,J=7.0Hz,3H).

[0118] Compound 1-267: 1 H NMR(600MHz,Chloroform-d)δ7.91(d,J=8.0Hz,1H),7.13(d,J=8.0Hz,1H),4.02(t,J=6.6Hz,2H),3.64 (s,3H),3.26(s,3H),2.26(s,3H),2.08(s,3H),1.95–1.86(m,2H),1.69(s,3H),1.07(t,J=7.4Hz,3H).

[0119] Biotest Examples

[0120] Example 2: Determination of herbicidal activity

[0121] Broadleaf weeds (zinnia, velvetleaf) or grass weeds (setaria, barnyard grass) seeds were sown in 7 cm diameter paper cups filled with nutrient soil, covered with 1 cm of soil after sowing, pressed and watered, and then cultured in a greenhouse according to conventional methods. After the weeds reached the 2-3 leaf stage, the stems and leaves were sprayed.

[0122] After the original drug was dissolved in acetone, the test solution of the required concentration was prepared by adding 1‰ Tween 80 to tap water according to the test requirements. According to the designed dose, the spray treatment was carried out on a crawler crop sprayer (designed and produced by Engineer Research Ltd., UK) (spray pressure 1.95kg / cm 2 , spray volume 500L / hm 2, crawler speed 1.48 km / h). The test was repeated three times. After treatment, the test materials were placed in the operating hall. After the pesticide solution dried naturally in the shade, they were placed in the greenhouse and managed according to conventional methods. The response of the weeds to the pesticide was observed and recorded. After treatment, the control effect of the test pesticide on weeds was visually inspected regularly. The control effect is expressed on a scale of 0 to 100%, with "0" representing no control effect and "100%" representing complete kill.

[0123] The test results show that the compounds of general formula I generally have high control efficacy against broadleaf weeds and grass weeds. Among some of the tested compounds, such as compounds I-2, I-158, I-159, I-162, I-170, I-203, I-225, I-226, I-230, I-232 and I-267, at a dose of 600 g ai / hm 2 It has good control effect on zinnia, velvetleaf, foxtail grass and barnyard grass, with the control effect being greater than or equal to 95%.

[0124] Table 2: Activity of some compounds of formula I and control compounds against Zinnia herba (post-emergence, control effect %)

[0125]

[0126]

[0127] According to the above test method, some compounds of general formula I and control compounds were selected to conduct activity tests on controlling velvetleaf. The results are shown in Table 3.

[0128] Table 3: Activity of some compounds of formula I and reference compounds against velvetleaf (post-emergence, control effect %)

[0129]

[0130] According to the above test method, some compounds of general formula I and control compounds were selected to conduct activity tests on controlling Setaria viridis. The results are shown in Table 4.

[0131] Table 4: Activity of some compounds of general formula I and reference compounds against Setaria viridis (post-emergence, control effect %)

[0132]

[0133]

[0134] According to the above test method, some compounds of general formula I and control compounds were selected to conduct activity tests on controlling barnyardgrass. The results are shown in Table 5.

[0135] Table 5: Activity of some compounds of formula I and reference compounds against barnyardgrass (post-emergence, control effect %)

[0136]

[0137] In summary, the compounds of the general formula of the present invention have herbicidal activity and can be used to control various weeds in agriculture. At the same time, the benzoylpyrazole compounds of the present invention not only have excellent herbicidal activity but are also safe for crops.

Claims

1. A benzoylpyrazole compound, characterized in that: The compound is shown in the general formula I: Where: R1 is selected from halogen or C1-C3 alkyl; R2 is selected from C1-C3 alkoxy, C1-C3 alkoxy C1-C3 alkyl or C1-C3 alkoxy C1-C3 alkoxy; R3 is selected from C1-C3 alkyl; R4 is selected from C1-C3 alkyl; R5 is selected from H, C1-C3 alkyl or C3-C6 cycloalkyl. When R1 is selected from methyl, R5 is selected from H, R2 is not 2. The compound according to claim 1, characterized in that In the general formula I: R1 is selected from Cl, Br, methyl, ethyl, n-propyl or isopropyl; R2 is selected from methoxymethyl, methoxyethoxy or propoxy; R3 is selected from methyl, ethyl, n-propyl or isopropyl; R4 is selected from methyl, ethyl, n-propyl or isopropyl; R5 is selected from H, methyl, ethyl, n-propyl, isopropyl or cyclopropyl. When R1 is selected from methyl, R5 is selected from H, R2 is not 3. Use of the compound of general formula I according to claim 1 in controlling weeds.

4. A herbicidal composition, characterized in that: The herbicidal composition comprises an active substance and an agriculturally acceptable carrier, wherein the active component is the compound of general formula I according to claim 1, and the weight percentage of the active component in the composition is 1-99%.

5. A method for controlling weeds using the herbicidal composition according to claim 4, characterized in that: Applying a herbicidally effective amount of the herbicidal composition according to claim 4 to weeds or a growth medium or site of weeds.

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