A benzimidazole compound and its preparation and application in resisting agricultural pathogenic fungi

Abstract

The invention belongs to the field of antimicrobial agents, and discloses a benzimidazole compound for plant pathogen control, its preparation, and application in resisting agricultural pathogenic fungi. The benzimidazole compound for plant pathogen control has a general structural formula as shown in Formula I; the compound provided by Formula I has a good inhibitory effect on plant pathogens, especially has a good antibacterial activity against Phytophthora infestans and citrus spherical fungi; the compound of Formula I has a good toxicity and growth inhibition effect on plant pathogens such as Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, citrus spherical fungi, Phytophthora infestans, rice blast fungus, Higgins spiny spore, Fusarium oxysporum, etc.

Description

Technical Field

[0001] The invention belongs to the field of antimicrobial agents, and particularly relates to a benzimidazole compound for preventing and controlling plant pathogens, and a preparation method thereof and an application thereof in resisting agricultural pathogenic fungi. Background Art

[0002] Antimicrobial agents are key production materials for preventing and controlling plant pathogens to ensure high-quality and high-yield crops. However, with the long-term use and even abuse of pesticides, plant diseases have developed serious resistance to existing pesticides, making their prevention and control increasingly difficult. It is very necessary to develop new antimicrobial agents to improve the prevention and control of plant diseases.

[0003] The commercialized benzimidazole fungicides mainly include carbendazim, benomyl, and thiabendazim. Excessive use of carbendazim causes plant resistance, and excessive residues can cause harm to mammals. The European Union has begun to ban carbendazim in agricultural applications. Thiabendazim is highly effective, broad-spectrum, and has no chronic toxicity problems, but it is easily decomposed by heat and is easily harmful to the environment. Benomyl has also been banned in many countries due to its toxic effects. These antimicrobial agents mainly modify the carbamate or urea active groups at the 2nd position of benzimidazole. Through literature research, it was found that derivatives substituted at the 1st position of benzimidazole have different degrees of antibacterial activity against bacteria in the medical field, but there are few reports on the inhibition of plant pathogens. The cell structure of plant pathogenic fungi is very different from that of bacteria, and the harm of plant diseases caused by fungi is particularly serious. The inhibitory activity of 1-substituted benzimidazole derivatives against plant pathogenic fungi is difficult to predict. A large amount of design and activity screening of such compounds is required to obtain highly active lead compounds. Summary of the invention

[0004] In order to overcome the above-mentioned shortcomings and deficiencies of the prior art, the primary purpose of the present invention is to provide a benzimidazole compound for controlling plant pathogens.

[0005] Another object of the present invention is to provide a method for preparing the benzimidazole compounds for controlling plant pathogens.

[0006] Another object of the present invention is to provide the application of the above-mentioned benzimidazole compounds in the field of agriculture, especially in the preparation of drugs against agricultural pathogenic fungi.

[0007] The purpose of the present invention is achieved through the following solutions:

[0008] A benzimidazole compound for controlling plant pathogens, the general structural formula of which is shown in the following general formula I:

[0009]

[0010] in:

[0011] A is selected from one of C, O, S and Se;

[0012] n is an integer selected from 1, 2 or 3;

[0013] R 1 It is a substituent at any position on the benzene ring, which can be single-substituted or multi-substituted. When multi-substituted, multiple R 1 They are independent of each other and can be the same or different;

[0014] R 1 Relatively independently selected from hydrogen, halogen, C1-C 12 Alkyl, C1-C 12 Alkoxy, C1-C 12 Alkylthio, halogenated C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy, halogenated C1-C 12 Alkylthio, C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, C3-C 12 Cycloalkyl, C6-C 20 One of the aromatic groups;

[0015] R 2 It is a substituent at any position on the benzene ring, which can be single-substituted or multi-substituted. When multi-substituted, multiple R 2 Independent of each other, they can be the same or different;

[0016] R 2 Relatively independently selected from hydrogen, halogen, -CN, -NO2, -OH, -SH, C1-C 12 Alkyl, C1-C 12 Alkoxy, C1-C 12 Alkylthio, halogenated C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy, halogenated C1-C 12 Alkylthio, C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, C3-C 12 Cycloalkyl, C6-C 20 One of the aromatic groups;

[0017] R 3 Selected from hydrogen, halogen, C1-C 12 Alkyl, C1-C 12 Alkoxy, C1-C 12 Alkylthio, halogenated C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy, halogenated C1-C12 Alkylthio, C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, C3-C 12 Cycloalkyl, C6-C 20 One of the aromatic groups.

[0018] Further preferably, in the general formula I, A is selected from one of C, O, and S. In this case, according to the different atoms of A, the compound I can be further classified into compounds IA, IB, and IC, and their general formulas are shown below:

[0019]

[0020] In compounds IA, IB and IC:

[0021] n is an integer selected from 1, 2 or 3;

[0022] R 1 It is a substituent at any position on the benzene ring, which can be single-substituted or multi-substituted. When multi-substituted, multiple R 1 They are independent of each other and can be the same or different;

[0023] R 1 and independently selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkyl, halogenated C1-C4 alkoxy, halogenated C1-C4 alkylthio, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyl, C6-C 12 One of the aromatic groups;

[0024] R 2 It is a substituent at any position on the benzene ring, which can be single-substituted or multi-substituted. When multi-substituted, multiple R 2 Independent of each other, they can be the same or different;

[0025] R 2 Relatively independently selected from hydrogen, halogen, -CN, -NO2, -OH, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkyl, halogenated C1-C4 alkoxy, halogenated C1-C4 alkylthio, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyl, C6-C 12 One of the aromatic groups;

[0026] R 3is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkyl, halogenated C1-C4 alkoxy, halogenated C3-C6 alkylthio, C6-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, C3-C6 cycloalkyl, C6-C 12 One of the aromatic groups.

[0027] In the present invention, the alkyl group of the aforementioned alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, alkylcarbonyl and alkoxycarbonyl may be linear or branched; preferably, the alkyl group of the aforementioned alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, alkylcarbonyl and alkoxycarbonyl is one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, 2-methylpentyl, heptyl and octyl, and more preferably one of methyl, ethyl, propyl, isopropyl, butyl and tert-butyl.

[0028] In the present invention, the aforementioned halogen is selected from one of fluorine, chlorine, bromine and iodine; preferably fluorine, chlorine or bromine.

[0029] In the present invention, in the aforementioned halogenated alkyl, halogenated alkoxy, halogenated alkylthio, halogen is selected from fluorine, chlorine, bromine, iodine; preferably fluorine, chlorine or bromine. The halogenated refers to that the hydrogen atoms of the alkyl part are partially or completely replaced by halogen atoms, and the halogenated alkyl part is chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, bromomethyl, dibromomethyl, tribromomethyl, chlorodifluoromethyl, fluorodichloromethyl, bromodichloromethyl, bromodifluoromethyl, chlorodibromomethyl, or fluorodibromomethyl.

[0030] In the present invention, the cycloalkyl group is selected from cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or adamantyl.

[0031] In the present invention, the aforementioned aryl group is selected from phenyl, naphthyl, anthracenyl, or fluorenyl.

[0032] Preferably, the benzimidazole compound is a compound represented by the following structural formula, but the present invention is not limited to these compounds:

[0033]

[0034] A method for preparing the above-mentioned benzimidazole compound for controlling plant pathogens, wherein the reaction pathway is as shown in (1) or (2):

[0035]

[0036]

[0037] In the reaction formula, R 1 ,R 2 ,R 3 ,n is as defined above in this document.

[0038] The method for preparing the benzimidazole compound for controlling plant pathogens, reaction path (1) specifically comprises the following steps:

[0039] Step 1: The compound represented by formula I-1 reacts with Br-(CH2)n-Br in an organic solvent under the action of a base to obtain an intermediate compound represented by formula I-2;

[0040] Step 2: Reaction of the intermediate compound represented by formula I-2 with In the presence of a base, the reaction is heated in an organic solvent to obtain a compound of the general formula (I).

[0041] The base in step 1 is selected from potassium tert-butoxide, sodium tert-butoxide, lithium tert-butoxide, potassium ethoxide, sodium ethoxide, lithium ethoxide, potassium carbonate, lithium carbonate, sodium carbonate or a mixture thereof. Preferably, it is potassium tert-butoxide, sodium tert-butoxide, lithium tert-butoxide or potassium carbonate or a mixture thereof.

[0042] The organic solvent used in the reaction of step 1 is selected from any one of acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, 1,4-dioxane or a mixture thereof. Preferably, the organic solvent is selected from at least one of N,N-dimethylformamide and acetonitrile.

[0043] In step 1, the molar ratio of the compound represented by formula I-1 to Br-(CH2)n-Br is 1:6-8; the molar ratio of the compound represented by formula I-1 to the base is 1:2.

[0044] The heating temperature in the reaction of step 1 is 40-140° C., preferably 80° C.; the reaction is continued until the reaction is completed as monitored by TLC.

[0045] The reaction in step 1 is carried out in an atmosphere of air, nitrogen, or argon; preferably in an atmosphere of nitrogen or argon.

[0046] The base described in the reaction of step 2 is selected from any one of potassium tert-butoxide, sodium tert-butoxide, lithium tert-butoxide, potassium ethoxide, sodium ethoxide, lithium ethoxide, potassium carbonate, lithium carbonate, and sodium carbonate, or a mixture thereof. Preferably, it is any one of potassium tert-butoxide, sodium tert-butoxide, lithium tert-butoxide, and potassium carbonate.

[0047] The organic solvent used in the reaction of step 2 is selected from any one of acetone, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, 1,4-dioxane or a mixture thereof. Preferably, the organic solvent is selected from at least one of N,N-dimethylformamide and acetone.

[0048] The intermediate compound in step 2 and The molar ratio of the intermediate compound to the base is 1:2.

[0049] The heating temperature in the reaction of step 2 is 40-140° C., preferably 80° C.; the reaction is continued until the reaction is completed as monitored by TLC.

[0050] The reaction in step 2 is carried out under an atmosphere of air, nitrogen, or argon, preferably under an atmosphere of nitrogen or argon.

[0051] The method for preparing the benzimidazole compound for controlling plant pathogens, reaction path (2) specifically comprises the following steps:

[0052] Step 3: Compound represented by formula I-1 and Under the action of sodium hydride, the reaction is carried out in an organic solvent to obtain a compound shown in formula I.

[0053] The organic solvent used in the reaction of step 3 is selected from any one of acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, 1,4-dioxane or a mixture thereof. Preferably, the organic solvent is selected from at least one of N,N-dimethylformamide and acetonitrile.

[0054] In step 3, the compound represented by formula I-1 and The molar ratio of the compound represented by formula I-1 to sodium hydride is 1:1.5.

[0055] The reaction temperature of step 3 is room temperature, and the reaction is continued until the reaction is completed as monitored by TLC.

[0056] The reaction in step 3 is carried out in an atmosphere of air, nitrogen, or argon; preferably in an atmosphere of nitrogen or argon.

[0057] The benzimidazole compounds for controlling plant pathogens are pesticide-acceptable salts, stereoisomers, prodrugs thereof or pharmaceutically acceptable solvent compounds.

[0058] The pharmaceutically acceptable salt is an organic salt or an inorganic salt formed by the above-mentioned benzimidazole compound for controlling plant pathogens and an organic acid or an organic acid, wherein the inorganic acid salt is a hydrochloride, a hydrobromide, a nitrate, a sulfate or a phosphate, and the organic acid salt is a formate, an acetate, a propionate, a benzoate, a maleate, a fumarate, a succinate, a tartrate, a citrate, an alkyl sulfonate or an aryl sulfonate.

[0059] A composition comprises an active component and a pesticide-acceptable carrier, excipient or diluent, wherein the active component is the above-mentioned benzimidazole compound, its pesticide-acceptable salt, stereoisomer, prodrug or pharmaceutically acceptable solvent compound, and the weight percentage of the active component in the composition is 0.01-99.99%.

[0060] The above composition may also include one or more fungicides, plant growth regulators or fertilizers.

[0061] Use of the above-mentioned benzimidazole compounds, pesticide-acceptable salts, stereoisomers, prodrugs or pharmaceutically acceptable solvent compounds of the benzimidazole compounds, and the above-mentioned compositions in the preparation of antibacterial agents.

[0062] The antibacterial agent is used for inhibiting and killing plant pathogens.

[0063] The plant pathogenic fungus refers to at least one of the fungi of the subdivision Ascomycetes, the subdivision Basidiomycetes, the subdivision Ascomycetes, the subdivision Zusammeniae and the subdivision Mastigoycetes; preferably at least one of the fungi of Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, Phytophthora infestans, Magnaporthe oryzae, Colletotrichum higginsii and Fusarium oxysporum.

[0064] The mechanism of the present invention is:

[0065] During the creation process, the inventors hoped to use the active fragments of non-toxic or low-toxic natural compounds as starting materials to create antibacterial agents. 12After chemical modification and grafting of the structural unit 5,6-dimethylbenzimidazole with the natural product phenoxyethanol, it has good anti-plant pathogen activity. On this basis, the inventors finally obtained the 1-substituted benzimidazole anti-plant pathogen lead as shown in the general formula compound I by screening the active groups. Such compounds have different degrees of inhibitory effects on Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, Guignardia citricarpa Kiely, Phytophthora infestans, Pyricularia oryzae Cavara, Colletotrichum higginsianum, Fusarium oxysporum, etc.

[0066] Compared with the prior art, the present invention has the following advantages and beneficial effects:

[0067] The compounds provided by the general formula I of the present invention have good inhibitory effects on plant pathogens, especially have excellent antibacterial activity against Phytophthora infestans and Phytophthora citri sphaerocephala; the compounds of the general formula I have good toxicity and growth inhibition effects on plant pathogens such as Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, Phytophthora infestans, Rice blast fungus, Higgins's spiny spores, and Fusarium oxysporum. DETAILED DESCRIPTION

[0068] The present invention is further described in detail below in conjunction with the examples, but the embodiments of the present invention are not limited thereto. If the specific conditions are not specified in the examples, they are carried out according to conventional conditions or conditions recommended by the manufacturer. If the manufacturer of the reagents or instruments used is not specified, they are all conventional products that can be purchased commercially.

[0069] Unless otherwise specified, the reagents used in the examples can be purchased from the market.

[0070] Example 1: Preparation of Compound IB-12

[0071] (1) Preparation of 5,6-dimethylbenzimidazolyl bromide

[0072]

[0073] Add 5,6-dimethylbenzimidazole (0.2mmol), 1,2-dibromoethane (1.2mmol), potassium carbonate (0.4mmol) to a sealed tube, dissolve with 2mL acetonitrile (MeCN) in a nitrogen atmosphere, seal the reaction tube and place it in a 70°C oil bath to stir and react for 12h. After the reaction is completed, monitor the reaction by thin layer chromatography (TLC). After the reaction is completed, the reaction mixture is cooled to room temperature, extracted with ethyl acetate solution, and the organic phases are combined and dried over anhydrous Na2SO4 and the solvent is evaporated under reduced pressure. The residue is purified by column chromatography (eluted with a mixed solvent of petroleum ether and ethyl acetate in a ratio of 10:1) to obtain a yellow solid product with a yield of 80.0%.

[0074] (2) Preparation of Compound IB-12

[0075]

[0076] Add 1-(2-bromoethyl)-5,6-dimethyl-1H-benzimidazole (0.20mmol), o-trifluoromethylphenol (0.40mmol), potassium carbonate (0.40mmol) to a sealed tube, dissolve with 2mL acetone (Me2CO) in a nitrogen atmosphere, seal the reaction tube and place it in a 60°C oil bath to stir and react for 12h. After the reaction is completed by TLC monitoring, the reaction mixture is cooled to room temperature, extracted with ethyl acetate solution, the organic phases are combined and dried over anhydrous Na2SO4, and the solvent is evaporated under reduced pressure. The residue is purified by column chromatography (eluted with a 1:1 mixed solvent of petroleum ether and ethyl acetate) to obtain a yellow liquid product with a yield of 50.0%.

[0077] Example 2: Preparation of Compound IB-18

[0078]

[0079] Add 1-(2-bromoethyl)-5,6-dimethyl-1H-benzimidazole (0.20mmol), 3,5-dichlorophenol (0.40mmol), potassium carbonate (0.40mmol) to a sealed tube, dissolve with 2mL acetone (Me2CO) in a nitrogen atmosphere, seal the reaction tube and place it in a 60℃ oil bath to stir and react for 12h. After the reaction is completed by TLC monitoring, the reaction mixture is cooled to room temperature, extracted with ethyl acetate solution, and the organic phases are combined and dried over anhydrous Na2SO4 and the solvent is evaporated under reduced pressure. The residue is purified by column chromatography (eluted with a mixed solvent of petroleum ether and ethyl acetate 1:1) to obtain a yellow liquid product with a yield of 65.0%.

[0080] Example 3: Preparation of Compound IB-21

[0081]

[0082] 1-(2-bromoethyl)-5,6-dimethyl-1H-benzimidazole (0.20mmol), 3,5-difluorophenol (0.40mmol), potassium carbonate (0.40mmol) were added to a sealed tube, dissolved with 2mL acetone (Me2CO) in a nitrogen atmosphere, sealed and placed in a 60°C oil bath for 12h of stirring. After the reaction was completed by TLC monitoring, the reaction mixture was cooled to room temperature, extracted with ethyl acetate solution, the organic phases were combined and dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluted with a 1:1 mixed solvent of petroleum ether and ethyl acetate) to obtain a white solid product with a yield of 75.0%.

[0083] Example 4: Preparation of Compound IB-22

[0084]

[0085] 1-(2-bromoethyl)-5,6-dimethyl-1H-benzimidazole (0.20mmol), 3,4-difluorophenol (0.40mmol), potassium carbonate (0.40mmol) were added to a sealed tube, dissolved with 2mL acetone (Me2CO) in a nitrogen atmosphere, sealed and placed in a 60°C oil bath for 12h of stirring. After the reaction was completed by TLC monitoring, the reaction mixture was cooled to room temperature, extracted with ethyl acetate solution, the organic phases were combined and dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluted with a 1:1 mixed solvent of petroleum ether and ethyl acetate) to obtain a white solid product with a yield of 65.0%.

[0086] Example 5: Preparation of Compound IA-1

[0087]

[0088] Add 1-bromo-3-phenylpropane (0.40mmol) and 5,6-dimethylbenzimidazole (0.20mmol) to a sealed tube, dissolve with 2mL N,N-dimethylformamide (DMF), add sodium hydride (0.3mmol) in an ice bath at 0℃ and stir for half an hour, then seal the reaction tube and stir at room temperature for 12h. After the reaction is completed by TLC monitoring, the reaction mixture is cooled to room temperature, extracted with ethyl acetate solution, the organic phases are combined and dried over anhydrous Na2SO4, and the solvent is evaporated under reduced pressure. The residue is purified by column chromatography (eluted with a mixed solvent of petroleum ether and ethyl acetate in a ratio of 1:1) to obtain a yellow liquid with a yield of 45.0%.

[0089] Example 6: Preparation of Compound IC-1

[0090]

[0091] 1-(2-bromoethyl)-5,6-dimethyl-1H-benzimidazole (0.20mmol), thiophenol (0.40mmol), potassium carbonate (0.40mmol) were added to a sealed tube, dissolved with 2mL acetone (Me2CO) in a nitrogen atmosphere, sealed and placed in a 60°C oil bath for 12h of stirring. After the reaction was completed by TLC monitoring, the reaction mixture was cooled to room temperature, extracted with ethyl acetate solution, the organic phases were combined and dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (eluted with a 1:1 mixed solvent of petroleum ether and ethyl acetate) to obtain a yellow liquid product with a yield of 60.0%.

[0092] IB-1 to IB-24 were prepared by the method of IB-12 in Reference Example 1.

[0093] IA-1 to IA-3 were prepared according to the method of IA-1 in Reference Example 5.

[0094] IC-1~IC-2 were prepared by the method of IC-1 in Reference Example 6.

[0095] NMR data of some compounds (unless otherwise specified, the rest of the compounds: 1 H NMR, 500 MHz; 13 C NMR, 125 MHz, internal standard TMS, solvent: CDCl3) is shown below:

[0096] Compound IA-1: yellow liquid. H 7.84(s,1H),7.62(s,1H),7.33(t,J=7.5Hz,2H),7.25(t,J=7.3Hz,1H),7.19(d,J=7.3Hz,2H),7.1 2(s,1H),4.14(t,J=7.0Hz,2H),2.67(t,J=7.5Hz,2H),2.40(d,J=6.4Hz,6H),2.32–2.17(m,2H).δ C 142.34,142.21,140.32,132.29,132.24,131.27,128.70,128.47,126.44,120.29,110.00,44.32,32.73,30.97,20.65,20.31.

[0097] Compound IA-2: yellow liquid. H7.61(s,1H),7.56(s,1H),7.27(m,2H),7.16(s,1H),7.04(d,J=7.0Hz,1H ),4.34(t,J=7.1Hz,1H),3.12(t,J=7.0Hz,1H),2.41(d,J=10.8Hz,3H).δ C 142.35,142.19,137.68,132.14,132.04,131.11,128.79,128.66,126.98,120.30,109.83,46.69,36.23,20.60,20.27.

[0098] Compound IA-3: white solid. H 7.88(d,J=31.4Hz,1H),7.60(s,1H),6.99(s,1H),6.74(t,J=8.7Hz,1H),6.65(d,J=5.9Hz,2H),5.29(s,2H),2.36(d,J=15.0Hz,6H).δ C 164.0(d,J=12.7Hz),162.41(d,J=12.7Hz),142.51,142.28,139.94(t,J=8.7Hz),132.77,132.18,13 1.61, 120.60, 109.75 (d, J = 6.2Hz), 109.59 (d, J = 6.3Hz), 103.67 (t, J = 25.2Hz), 47.80, 20.57, 20.22.

[0099] Compound IB-1: yellow liquid. H 8.09(s,1H),7.85(d,J=7.8Hz,1H),7.50(d,J=7.7Hz,1H),7.40–7.23(m,4H),6.98(t ,J=7.4Hz,1H),6.86(d,J=8.0Hz,2H),4.58(t,J=5.2Hz,2H),4.32(t,J=5.2Hz,2H).δ C 158.00,143.69,132.69,129.72,123.20,122.43,121.71,120.56,114.62,109.62,66.53,44.61,1.63.

[0100] Compound IB-2: yellow liquid. H7.76–7.68(m,1H),7.41–7.34(m,1H),7.27(dd,J=14.4,6.9Hz,4H),6.96(t,J=7.4Hz, 1H),6.81(d,J=8.0Hz,2H),4.51(t,J=5.3Hz,2H),4.27(t,J=5.4Hz,2H),2.72(s,3H).δ C 157.95,152.22,142.63,135.00,129.58,122.17,122.06,121.48,119.18,114.31,108.99,65.83,43.38,14.08.

[0101] Compound IB-3: yellow liquid. H 7.91(d,J=8.2Hz,1H),7.69(d,J=8.3Hz,1H),7.49(t,J=7.6Hz,1H),7.42(t,J=7.6Hz,1H),7.27(dd,J=8. 1,7.3Hz,2H),6.97(t,J=7.4Hz,1H),6.83(d,J=8.1Hz,2H),4.76(t,J=5.5Hz,2H),4.36(t,J=5.5Hz,2H).δ C 157.80,141.03,136.03,129.58,125.44,123.82,121.59,121.57,114.28,111.30,66.21,44.54,44.53.

[0102] Compound IB-4: yellow liquid. H 7.88–7.81(m,1H),7.58–7.51(m,1H),7.38–7.30(m,1H),7.26–7.18(m,1H),6.94(t ,J=7.3Hz,1H),6.75(d,J=7.9Hz,1H),4.64(t,J=5.7Hz,1H),4.28(t,J=5.7Hz,1H).δ C 158.01,154.20,143.13,135.73,130.43,129.85,129.71,129.54,128.76,122.95,122.66,121.42,120.08,114.33,110.24,65.80,44.15.

[0103] Compound IB-5: white solid. H8.09(s,1H),7.85(d,J=7.8Hz,1H),7.50(d,J=7.7Hz,1H),7.40–7.23(m,4H),6.98(t ,J=7.4Hz,1H),6.86(d,J=8.0Hz,2H),4.58(t,J=5.2Hz,2H),4.32(t,J=5.2Hz,2H).δ C 157.95,142.83,142.31,132.32,132.17,131.11,129.57,121.49,120.38,114.51,109.75,77.41,77.16,76.90,66.04,44.37,20.61,20.23.

[0104] Compound IB-6: yellow liquid. H 8.03(s,1H),7.82–7.67(m,3H),7.62(s,1H),7.48–7.42(m,1H),7.40–7.33(m,1H),7.28(s,2 H),7.16–7.02(m,2H),4.60(t,J=5.2Hz,2H),4.42(t,J=5.3Hz,2H),2.42(d,J=19.9Hz,6H).δ C 155.86,134.28,132.47,132.23,131.47,129.69,129.27,127.68,126.73,126.54,124.01,120.27,118.53,109.78,106.85,66.08,44.47,29.70,20.63,20.22.

[0105] Compound IB-7: yellow liquid. H 7.97(s,1H),7.58(s,1H),7.22(s,1H),6.81–6.74(m,4H),4.49(t,J=5.3Hz,2H),4.24(t,J=5.3Hz,2H),3.75(s,3H),2.39(d,J=15.0Hz,6H).δ C 154.41,152.09,142.80,132.25,120.27,115.63,114.75,109.74,66.87,55.71,44.56,29.70,20.60,20.21.

[0106] Compound IB-8: yellow liquid. H8.04(s,1H),7.58(s,1H),7.25(d,J=11.6Hz,1H),7.02–6.71(m,5H),4.52(t ,J=5.3Hz,2H),4.31(t,J=5.3Hz,2H),3.82(s,3H),2.38(d,J=13.9Hz,6H).δ C 149.93,147.62,143.08,132.36,132.10,122.41,121.76,120.95,120.84,120.29,114.55,112.24,109.78,67.84,55.88,44.49,20.60,20.22.

[0107] Compound IB-9: yellow liquid. H 7.94(s,1H),7.58(s,1H),7.22(s,1H),7.14(t,J=8.2Hz,1H),6.51(dd,J=8.2,2.1Hz,1H),6.43(dd,J=8.2,2.0H z,1H),6.39(t,J=2.3Hz,1H),4.48(t,J=5.3Hz,2H),4.25(t,J=5.3Hz,2H),3.75(s,3H),2.39(d,J=15.4Hz,6H).δ C 160.90,159.18,142.82,142.15,132.26,131.22,130.02,120.35,109.73,107.15,106.56,101.11,66.09,55.29,44.39,29.71,20.60,20.22.

[0108] Compound IB-10: yellow liquid. H 8.10(s,1H),7.92(s,1H),7.66(s,1H),7.29(t,J=8.0Hz,3H),6.99(t,J=7.4 Hz,1H),6.85(d,J=8.0Hz,2H),4.55(t,J=4.7Hz,2H),4.32(t,J=4.8Hz,2H).δ C 157.63,129.68,127.36,126.64,121.82,121.55,114.42,111.38,66.09,44.96.

[0109] Compound IB-11: yellow liquid. H8.04(s,1H),7.60(s,1H),7.36(t,J=8.0Hz,1H),7.25–7.18(m,2H),7.06(s,1H),7.0 3–6.97(m,1H),4.57(t,J=5.2Hz,2H),4.33(t,J=5.2Hz,2H),2.39(d,J=19.9Hz,6H).δ C 158.00,132.66,132.11,131.86,130.14,122.67,120.25,118.28(q,J=3.8Hz),118.14,111.10,109.70,66.36,44.40,29.70,20.59,20.20.

[0110] Compound IB-12: yellow liquid. H 7.95(s,1H),7.56(t,2H),7.42(t,J=7.9Hz,1H),7.21(s,1H),7.01(t,J=7.6Hz,1H),6.85 (d,J=8.4Hz,1H),4.57(t,J=5.1Hz,2H),4.34(t,J=5.1Hz,2H),2.40(s,3H),2.37(s,3H).δ C 155.97,143.19,133.42,132.36,132.16,131.29,127.45(m,J=5.2Hz),124.73,122 .56,121.08,120.66,119.42,119.18,112.79,109.52,67.13,44.36,20.66,20.33.

[0111] Compound IB-13: yellow liquid. H 7.98(s,1H),7.59(s,1H),7.50(d,J=8.7Hz,2H),7.23(s,1H),6.89(d,J=8.6H z,2H),4.55(t,J=5.2Hz,2H),4.32(t,J=5.2Hz,2H),2.39(d,J=18.2Hz,6H).δ C164.61(d,J=15.6Hz),162.65(d,J=15.6Hz),159.84,159.74,159.63,142.65,132.51,132.11,131.46,1 20.45,109.57,98.47(d,J=7.2),98.30(d,J=7.23Hz),97.20(t,J=25.8Hz),66.66,44.12,20.60,20.19.

[0112] Compound IB-14: yellow liquid. H 7.99(s,1H),7.60(s,1H),7.46(s,1H),7.23(s,3H),4.59(t,J=5.1Hz,2H),4.38(t,J=5.1Hz,2H),2.39(d,J=20.4Hz,6H).δ C 158.39,153.30,133.93,133.05,132.79,132.38,131.82,130.56,129.75,129.47,129.21,129.05,128.79,128.69 ,125.93,124.03,121.86,120.35,114.98(q,J=3.9Hz),114.68(d,J=3.15Hz),110.01,66.56,43.59,20.64,20.23.

[0113] Compound IB-15: yellow liquid. H 8.04(s,1H),7.61(s,1H),7.25(s,1H),7.19(t,J=8.2Hz,1H),6.96(dd,J=8.0,1.0Hz,1H),6.86(t,J=2.0H z,1H),6.74(dd,J=8.3,2.3Hz,1H),4.56(t,J=5.2Hz,2H),4.30(t,J=5.2Hz,2H),2.42(d,J=16.8Hz,6H).δ C 158.63,134.96,132.38,131.59,131.31,130.36,121.70,120.37,114.89,113.01,109.70,66.32,44.26,20.60,20.20.δ C160.32,142.71,132.40,132.16,131.35,127.0(q,J=3.7Hz),125.30,123 .90,123.64,123.14,120.49,114.47,109.56,66.30,44.24,20.60,20.20.

[0114] Compound IB-16: yellow liquid. H 8.03(s,1H),7.57(s,1H),7.34(d,J=7.9Hz,1H),7.27(d,J=6.5Hz,1H),7.15(t,J=8.4Hz,1H),6.89(t,J= 7.7Hz,1H),6.78(d,J=8.2Hz,1H),4.57(t,J=5.1Hz,2H),4.30(t,J=5.1Hz,2H),2.39(d,J=14.3Hz,6H).δ C 153.62,143.09,132.22,132.17,131.11,130.49,127.67,123.12,122.21,120.41,113.26,109.72,67.42,44.30,29.70,20.54,20.20.

[0115] Compound IB-17: yellow liquid. H 7.94(s,1H),7.60(s,1H),7.27–7.16(m,3H),6.84–6.67(m,2H),4.52(t,J=5.2Hz,2H),4.26(t,J=5.2Hz,2H),2.41(d,J=15.1Hz,6H).δ C 156.56,142.76,142.26,132.32,132.22,131.27,129.45,126.48,120.46,115.79,109.62,66.45,44.32,20.61,20.21.

[0116] Compound IB-18: yellow liquid. H 7.94(s,1H),7.59(s,1H),7.20(s,1H),6.95(s,1H),6.72(s,2H),4.52(t,J=5.1Hz,2H),4.25(t,J=5.1Hz,2H),2.39(d,J=18.6Hz,6H).δ C158.85,142.62,135.53,132.51,132.07,131.46,121.90,120.46,113.60,109.53,66.60,44.14,29.70,20.61,20.20.

[0117] Compound IB-19: yellow liquid. H 7.94(s,1H),7.59(s,1H),7.20(s,1H),6.95(s,1H),6.72(s,2H),4.52(t,J=5.1Hz,2H),4.25(t,J=5.1Hz,2H),2.39(d,J=18.6Hz,6H).δ C 156.89,133.04,132.74,131.98,131.77,130.84,124.99,120.21,116.35,114.55,109.67,66.64,44.35,29.70,20.63,20.21.

[0118] Compound IB-20: white solid. H 7.91(s,1H),7.57(s,1H),7.21(s,1H),6.91(t,J=8.6Hz,2H),6.74(dd,J=9.0,4 .2Hz,2H),4.47(t,J=5.1Hz,2H),4.21(t,J=5.2Hz,2H),2.38(d,J=14.9Hz,6H).δ C 162.52,158.57,156.67,154.09,142.79,142.23,132.26,131.21,120.39,109.68,66.80,44.39,36.44,31.40,20.59,20.21.

[0119] Compound IB-21: yellow liquid. H 8.03(s,1H),7.59(s,1H),7.25–7.15(m,2H),6.69–6.60(m,2H),6.56(dt,J=10.7, 2.2Hz,1H),4.55(t,J=5.0Hz,2H),4.28(t,J=5.1Hz,2H),2.40(d,J=16.3Hz,5H).δ C164.67,162.72,159.36,142.62,132.79,132.19,131.82,130.59,130.51,120.29,110.37,109.89,108.66,102.59,66.48,44.56,29.85,22.84,20.77,20.36,14.26.

[0120] Compound IB-22: yellow liquid. H 8.04(s,1H),7.60(s,1H),7.23(s,1H),7.03(dd,J=18.8,9.2Hz,1H),6.65(ddd,J=11.6,6.5,3.0 Hz,1H),6.56–6.49(m,1H),4.54(t,J=5.1Hz,2H),4.24(t,J=5.2Hz,2H),2.40(d,J=17.1Hz,6H).

[0121] Compound IB-23: white solid. H 7.93(s,1H),7.59(s,1H),7.21(s,1H),6.45–6.33(m,3H),4.52(t,J=5.2Hz,2H),4.24(t,J=5.2Hz,2H),2.39(d,J=17.3Hz,6H).δ C 8.09,7.86,7.84,7.51,7.49,7.37,7.35,7.34,7.33,7.32,7.30,7.29,7.28,7.28,7.26,6.99,6.98,6.96,6.87,6.85,4.59,4.58,4.57,4.33,4.32,4.31.

[0122] Compound IB-24: white solid. H 7.99(s,1H),7.60(s,1H),7.46(s,1H),7.23(s,3H),4.59(t,J=5.1Hz,2H),4.38(t,J=5.1Hz,2H),2.39(d,J=20.4Hz,6H).δ C 158.44,142.67,133.15,132.88,132.71,131.99,131.67,124.03,121.87,120.49,11 5.16(m,J=3.9Hz),114.79(d,J=3.087Hz),109.51,66.84,44.16,29.70,20.59,20.20.

[0123] Compound IB-25: white solid. H 7.83–7.77(m,1H),7.59(s,1H),7.55–7.48(m,2H),7.29(s,1H),7.26–7.21(m,1H),6.94 (t,J=7.4Hz,1H),6.76(d,J=7.9Hz,1H),4.61(t,J=5.9Hz,1H),2.42(d,J=16.9Hz,3H).δ C 157.99,153.40,141.67,134.21,132.12,131.54,130.59,129.65,129.53,128.68,121.38,120.07,114.35,110.36,65.73,44.06,29.70,20.65,20.25.

[0124] Compound IC-1: white solid. H 7.81(s,1H),7.57(s,1H),7.40(d,J=7.3Hz,2H),7.34(t,J=7.5Hz,2H),7.28(d,J=7.2Hz ,1H),7.01(s,1H),4.30(t,J=7.0Hz,2H),3.30(t,J=7.0Hz,2H),2.37(d,J=1.8Hz,6H).δ C 142.29,134.06,132.44,131.83,131.46,130.66,129.34,127.27,120.34,109.54,44.15,33.92,20.58,20.22.

[0125] Compound IC-2: white solid. H 7.86(dd,J=5.6,3.2Hz,1H),7.70–7.61(m,2H),7.57–7.44(m,3H),7.38–7.18(m,8H),4.47(t,2H),3.20(t,2H).

[0126] Performance Example 1: Biological activity test, benzimidazole compounds were selected for antibacterial test.

[0127] The compound of the present invention exhibits good activity against a variety of pathogenic bacteria in the agricultural field, and the antibacterial activity test results are shown below.

[0128] (1) Evaluation of the in vitro antibacterial activity of some compounds against Rhizoctonia solani

[0129] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80 (Tween 80 aqueous solution)) to a concentration of 500 mg / L. 1 ml of the test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium (potato dextrose agar medium) were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28±1°C) for 4 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0130] (2) Evaluation of the in vitro antibacterial activity of some compounds against Phytophthora infestans

[0131] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of the test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of culture medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0132] (3) Evaluation of the in vitro antibacterial activity of some compounds against Botrytis cinerea

[0133] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0134] (4) Evaluation of the in vitro antibacterial activity of some compounds against Fusarium graminearum

[0135] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0136] (5) Evaluation of the in vitro antibacterial activity of some compounds against S. citri

[0137] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0138] (6) Evaluation of the in vitro antibacterial activity of some compounds against rice blast pathogen

[0139] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0140] (7) Evaluation of the in vitro antibacterial activity of some compounds against Higgins anthrax

[0141] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0142] (8) Evaluation of the in vitro antibacterial activity of some compounds against Fusarium oxysporum

[0143] Each test compound was dissolved in acetone and diluted with water (containing 0.1% TW-80) to a concentration of 500 mg / L. 1 ml of test solution and 9 ml of PDA (potato dextrose agar medium) were added to each culture dish to make the concentration of the test compound 50 mg / L, while 1 ml of distilled water containing 0.1% TW-80 and 9 ml of PDA medium were added to another culture dish as a blank control. A punch was used to cut the mycelial growth with a diameter of 6 mm on the growing fungal culture, and the mycelium was moved to the culture dish containing the test compound. Each analysis was performed three times. The culture dish was stored in a controlled environment cabinet (28 ± 1 ° C) for 5 days, after which the diameter of the mycelial growth was measured, and the inhibition percentage was calculated using the following equation: Inhibition percentage (%) = (average diameter of mycelium in the blank control - average diameter of mycelium in the drug tablet) / (average diameter of mycelium in the blank control - 6 mm) × 100. The test results are shown in Table 1.

[0144] Table 1. Antibacterial effect of benzimidazole compounds against agricultural pathogenic fungi (concentration 50 mg / L)

[0145]

[0146]

[0147] Table 2 Effect of some compounds of the present invention on the EC of Phytophthora infestans 50 Evaluate

[0148] Compound No. <![CDATA[EC 50 (mg / L)]]> Virulence regression equation 95% Confidence Interval r IB-4 7.271 y=0.8+0.93x 5.499-9.448 0.982 IB-6 3.507 y=0.66+1.23x 1.627～5.638 0.966 IB-8 2.424 y=0.56+1.52x 0.899～3.897 0.970 IB-15 7.844 y=1.16+1.41x 3.408～23.177 0.977 IB-16 3.357 y=0.5+0.93x 0.730～6.625 0.934 IB-18 2.279 y=0.45+11.36x 0.889～3.600 0.999 IB-19 1.671 y=0.42+2.1x 1.328～1.982 0.997 IB-22 1.754 y=0.29+1.48x 1.319-2.176 0.988 IB-25 4.393 y=0.91+1.3x 1.991-7.710 0.954

[0149] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be equivalent replacement methods and are included in the protection scope of the present invention.

Claims

1. A benzimidazole compound, characterized in that The benzimidazole compound is a compound represented by the following structural formula:

2. A method for preparing a benzimidazole compound, characterized in that: The reaction pathway is as follows (1) or (2): (1) (2) In the reaction path, A is selected from one of CH2, O, and S; n is selected from 2; R 1 It is a substituent at any position on the benzene ring, single or multiple substitution; when multiple substitutions are present, multiple R 1 Independent of each other, the same or different; R 1 Relatively independently selected from one of hydrogen, F, Cl, -CH3, -CF3; R 3 It is a substituent at any position on the benzene ring, single or multiple substitution; when multiple substitutions are present, multiple R 3 Independent of each other, the same or different; R 3 Relatively independently selected from one of hydrogen, Cl, and -CH3; R 2 One selected from hydrogen, -CH3, and phenyl; Reaction path (1) specifically includes the following steps: Step 1: The compound represented by formula I-1 reacts with Br-(CH2)n-Br in an organic solvent under the action of a base to obtain an intermediate compound represented by formula I-2; Step 2: Reaction of the intermediate compound represented by formula I-2 with In the presence of a base, heating the reaction in an organic solvent to obtain a compound of formula (I); Reaction path (2) specifically includes the following steps: Step 3: Compound represented by formula I-1 and Under the action of sodium hydride, the reaction is carried out in an organic solvent to obtain a compound shown in formula I.

3. The method for preparing the benzimidazole compound according to claim 2, characterized in that: In step 1, the molar ratio of the compound represented by formula I-1 to Br-(CH2)n-Br is 1:6-8; the molar ratio of the compound represented by formula I-1 to the base is 1:2; The intermediate compound in step 2 and The molar ratio of the intermediate compound to the base is 1:2; In step 3, the compound represented by formula I-1 and The molar ratio of the compound represented by formula I-1 to sodium hydride is 1:1.5; The reaction temperature of step 3 is room temperature.

4. The use of the benzimidazole compound according to claim 1 in the preparation of a plant antibacterial agent, characterized in that The fungus in the plant antibacterial agent refers to at least one of the fungi of the subdivision Ascomycota, the subdivision Basidiomycota, the subdivision Ascomycota, the subdivision Zusamycota and the subdivision Mastigomycota.

5. The use according to claim 4, characterized in that: The fungus in the plant antibacterial agent refers to at least one of Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, Phytophthora infestans, Magnaporthe oryzae, Colletotrichum higginsii, and Fusarium oxysporum.

6. Use of the benzimidazole compounds described in formula IA-1, IA-3, IB-1, IB-3, IB-4, IB-7, IB-8, IB-9, IB-11, IB-16, IB-17, IB-20, IB-21, and IC-1 in the preparation of plant antibacterial agents, characterized in that: The fungus in the plant antibacterial agent refers to at least one of the fungi of the subdivision Deuteromycotina, the subdivision Basidiomycotina, the subdivision Ascomycotina, the subdivision Zusamycotina and the subdivision Mastocotina; The structural formulas of the formulas IA-1, IA-3, IB-1, IB-3, IB-4, IB-7, IB-8, IB-9, IB-11, IB-16, IB-17, IB-20, IB-21, and IC-1 are as follows:

7. The use of the benzimidazole compound as claimed in claim 6 in the preparation of a plant antibacterial agent, characterized in that: The fungus in the plant antibacterial agent refers to at least one of Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, Phytophthora infestans, Magnaporthe oryzae, Colletotrichum higginsii, and Fusarium oxysporum.

8. A composition, characterized in that: The composition comprises an active component and a pesticide-acceptable carrier, excipient or diluent, wherein the active component is the benzimidazole compound according to claim 1, and the weight percentage of the active component in the composition is 0.01-99.99%.

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