1-methylcyclohexyl sulfone compound as well as preparation method and application thereof

Abstract

The invention discloses a 1-methyl cyclohexyl sulfone compound as well as a preparation method and application thereof. The compound has a structure as shown in a formula I, and can be prepared by substitution and oxidation reaction of 1-methylcyclohexyl halide and mercaptans with different substituent groups. The method disclosed by the invention is simple and convenient to operate and mild in condition, and the prepared 1-methylcyclohexyl sulfone compound has excellent herbicidal activity and can be used for preventing and treating agricultural weeds. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the field of agricultural herbicides, and specifically relates to a 1-methylcyclohexyl sulfone compound and a preparation method thereof and use thereof as a herbicide. Background Art

[0002] Cyclohexane derivatives are widely used in various types of pesticides, including insecticides, fungicides, etc. In order to explore the herbicidal activity of cyclohexane derivatives and enrich the biological properties of cyclohexane derivatives. Based on the principle of active substructure splicing, the present invention takes 1-methylcyclohexane as the guide, introduces sulfur-containing active group sulfone, and designs and synthesizes a new class of 1-methylcyclohexyl sulfone compounds. Combined with the bioassay experimental data, it is concluded that the compounds have excellent herbicidal activity and can be used to prevent agricultural weeds, and the herbicidal effect of some compounds can be significantly better than the commercially available herbicide glyphosate.

[0003] The 1-methylcyclohexyl sulfone compounds described in the present invention have not been reported in the prior art. Summary of the invention

[0004] The object of the present invention is to provide a 1-methylcyclohexyl sulfone compound and a preparation method thereof and use thereof as a herbicide, so as to meet the new requirements for herbicides constantly put forward in agriculture.

[0005] To achieve the above object, the technical solution of the present invention is as follows:

[0006] The present invention provides a 1-methylcyclohexyl sulfone compound, the structure of which is shown in Formula I:

[0007]

[0008] Where:

[0009] The R substituent is selected from one of methyl, cyclopropyl, cyclohexyl, 4-chlorophenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 4-thiotrifluoromethylphenyl, 3-chlorophenyl, 3-fluorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 4-pyridyl or 2-thienyl.

[0010] Preferably, the R substituent is selected from one of methyl, cyclopropyl, 4-fluorophenyl, 3-chlorophenyl, 3-fluorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl or 4-pyridyl.

[0011] It is further preferred that the R substituent is selected from one of 2,4-dichlorophenyl, 4-fluorophenyl, 3-chlorophenyl or 2,6-dichlorophenyl.

[0012] Most preferably the R group is selected from 4-fluorophenyl or 2,6-dichlorophenyl.

[0013] The synthetic route of the above-mentioned 1-methylcyclohexyl sulfone compound I is as follows:

[0014]

[0015] The specific preparation method comprises the following steps:

[0016] The step 1: in a suitable solvent, under the promotion of a base, compound II and compound III undergo a substitution reaction to obtain compound IV. Compound III is a thiol compound containing an R group.

[0017] The step 2: adding an oxidant in a suitable solvent, and subjecting compound IV to an oxidation reaction to obtain 1-methylcyclohexyl sulfone compound I.

[0018] Preferably, the compound II in step 1 is a 1-methylcyclohexyl halide, selected from any one of 1-methylcyclohexyl chloride, 1-methylcyclohexyl bromide or 1-methylcyclohexyl iodide, and most preferably 1-methylcyclohexyl chloride.

[0019] Preferably, the base in step 1 is selected from any one of potassium tert-butoxide, potassium carbonate, sodium carbonate or sodium ethoxide. Further preferably, the base in step 1 is selected from any one of potassium tert-butoxide or potassium carbonate.

[0020] Preferably, the molar ratio of the base in step 1 to compound II is (1.5-2):1.

[0021] Preferably, the molar ratio of compound II to compound III in step 1 is 1:(1.5-2).

[0022] Preferably, the solvent in step 1 is selected from any one of dimethyl sulfoxide, N,N-dimethylformamide or N,N-dimethylacetamide.

[0023] Preferably, the reaction temperature in step 1 is 25-80°C and the reaction time is 12 hours; preferably, the reaction temperature is 25-30°C.

[0024] Preferably, the solvent in step 2 is selected from any one of methanol, acetonitrile, or tetrahydrofuran.

[0025] Preferably, the oxidant in step 2 is hydrogen peroxide.

[0026] Preferably, the molar ratio of the oxidant to compound II in step 2 is (2-3):1.

[0027] Preferably, the reaction temperature in step 2 is 25-50°C, and the reaction time is 4-6 hours. Preferably, the reaction temperature is 25-30°C.

[0028] The present invention provides the use of the compound represented by formula I as a herbicide in the agricultural field.

[0029] The invention uses 1-methylcyclohexyl halides and mercaptan containing R substituents as raw materials, and obtains 1-methylcyclohexyl sulfone compounds with excellent herbicidal activity through substitution and oxidation reactions.

[0030] Compared with the prior art, the technical effects achieved by the present invention are:

[0031] 1. The preparation method of the compound provided by the present invention is simple, the raw materials are readily available, the reaction conditions are mild, the yield is high, and it is convenient for industrial production;

[0032] 2. The 1-methylcyclohexyl sulfone compounds provided by the present invention have novel structures, good herbicidal effects, and exhibit ideal herbicidal activity even at lower dosages, showing good prospects for development and utilization. DETAILED DESCRIPTION

[0033] The present invention is further illustrated below in conjunction with specific examples. It should be understood that these embodiments are only used to illustrate the present invention and do not limit the scope of the present invention. After reading the present invention, modifications of various equivalent forms of the present invention by those skilled in the art all fall within the scope defined by the claims attached to this application. The materials, reagents, etc. used in the following examples, unless otherwise specified, can all be obtained from commercial sources.

[0034] The specific compounds of formula I are listed in the following examples to illustrate the present invention, but are not intended to limit the present invention. See Table 1 for details.

[0035] Table 1

[0036]

[0037] The synthetic route is as follows:

[0038]

[0039] Example 1: Preparation of Compound I-1

[0040] Step 1: 1-Methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol) (purchased from Dalian Lianhua Chemical Co., Ltd., the same below), potassium tert-butoxide (1.12 g, 10 mmol), methyl mercaptan (0.36 g, 7.5 mmol), and 10 ml of N,N-dimethylacetamide were added to a reaction flask. After stirring at 25°C for 12 hours, 30 ml of saturated brine was added to the reaction solution, and the mixture was extracted with ethyl acetate (10 ml×3). The organic layer was concentrated under reduced pressure, and the concentrate was separated and purified by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0041] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of methanol, add hydrogen peroxide (30%, 1.1 g, 10 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-1, with a yield of 93%; HRMS (ESI) m / z:calcd for C 8 H 17 O 2 S[M+H] + 177.0945,found177.0942.

[0042] Example 2: Preparation of Compound I-2

[0043] Step 1: 1-Methylcyclohexyl bromide (Compound II) (0.88 g, 5 mmol) (purchased from Dalian Lianhua Chemical Co., Ltd., the same below), potassium carbonate (1.24 g, 9 mmol), cyclopropyl mercaptan (0.67 g, 9 mmol) and 10 ml of dimethyl sulfoxide were added to a reaction bottle. After stirring at 25°C for 12 hours, 30 ml of saturated brine was added to the reaction solution, and the mixture was extracted with ethyl acetate (10 ml×3). The organic layer was concentrated under reduced pressure, and the concentrate was separated and purified by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0044] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of methanol, add hydrogen peroxide (30%, 1.4 g, 12.5 mmol), stir at 40°C for 5 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-2, with a yield of 91%; HRMS (ESI) m / z:calcd for C 10 H 19 O 2 S[M+H] + 203.1101, found 203.1100.

[0045] Example 3: Preparation of Compound I-3

[0046] Step 1: 1-Methylcyclohexyl iodide (Compound II) (0.88 g, 5 mmol) (purchased from Dalian Lianhua Chemical Co., Ltd., the same below), sodium carbonate (0.79 g, 7.5 mmol), cyclohexyl mercaptan (1.16 g, 10 mmol) and 10 ml of N,N-dimethylformamide were added to a reaction flask. After stirring at 80°C for 12 hours, 30 ml of saturated brine was added to the reaction solution, and the mixture was extracted with ethyl acetate (10 ml×3). The organic layer was concentrated under reduced pressure, and the concentrate was separated and purified by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0047] Step 2: Compound IV obtained in step 1 was dissolved in 20 ml of acetonitrile, and hydrogen peroxide (30%, 1.7 g, 15 mmol) was added. After stirring at 50°C for 4 hours, the reaction solution was washed with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography (petroleum ether as eluent) to obtain compound I-3 with a yield of 92%; HRMS (ESI) m / z:calcd for C 13 H 25 O 2 S[M+H] + 245.1570, found 245.1567.

[0048] Example 4: Preparation of Compound I-4

[0049] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), sodium ethoxide (0.68 g, 10 mmol), 4-chlorophenylmercaptan (1.44 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction flask. After stirring at 50°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0050] Step 2: Compound IV obtained in step 1 was dissolved in 20 ml of tetrahydrofuran, and hydrogen peroxide (30%, 1.7 g, 15 mmol) was added. After stirring at 50°C for 6 hours, the reaction solution was washed with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography (petroleum ether as eluent) to obtain compound I-4 with a yield of 89%; HRMS (ESI) m / z:calcd for C 13 H 18 C1O 2 S[M+H] + 273.0711, found 273.0708.

[0051] Example 5: Preparation of Compound I-5

[0052] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 4-fluorophenylthiol (1.28 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0053] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of acetonitrile, add hydrogen peroxide (30%, 1.7 g, 15 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-5, with a yield of 88%; HRMS (ESI) m / z:calcd for C 13 H 18 FO 2 S[M+H] + 257.1007, found 257.1003.

[0054] Example 6: Preparation of Compound I-6

[0055] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium carbonate (1.38 g, 10 mmol), 4-trifluoromethylphenylthiol (1.78 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0056] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of acetonitrile, add hydrogen peroxide (30%, 1.7 g, 15 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-6, with a yield of 90%; HRMS (ESI) m / z:calcd for C 14 H 18 F 3 O2 S[M+H] + 307.0975, found 307.0974.

[0057] Example 7: Preparation of Compound I-7

[0058] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 4-thiotrifluoromethylphenylthiol (2.10 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0059] Step 2: Compound IV obtained in step 1 was dissolved in 20 ml of acetonitrile, and hydrogen peroxide (30%, 1.7 g, 15 mmol) was added. After stirring at 25°C for 6 hours, the reaction solution was washed with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography (petroleum ether as eluent) to obtain compound I-7 with a yield of 87%; HRMS (ESI) m / z:calcd for C 14 H 18 F 3 O 2 S 2 [M+H] + 339.0695,found339.0692.

[0060] Example 8: Preparation of Compound I-8

[0061] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 3-chlorophenylmercaptan (1.44 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction flask. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0062] Step 2: Compound IV obtained in step 1 was dissolved in 20 ml of acetonitrile, and hydrogen peroxide (30%, 1.7 g, 15 mmol) was added. After stirring at 25°C for 6 hours, the reaction solution was washed with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography (petroleum ether as eluent) to obtain compound I-8 with a yield of 91%; HRMS (ESI) m / z:calcd for C 13 H 18 C1O 2 S[M+H] + 273.0711, found 273.0710.

[0063] Example 9: Preparation of Compound I-9

[0064] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 3-fluorophenylthiol (1.28 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0065] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of acetonitrile, add hydrogen peroxide (30%, 1.7 g, 15 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-9 with a yield of 85%; HRMS (ESI) m / z:calcd for C 13 H 18 FO 2 S[M+H] + 257.1007, found 257.1005.

[0066] Example 10: Preparation of Compound I-10

[0067] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 2,4-dichlorophenylmercaptan (1.78 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction flask. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0068] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of acetonitrile, add hydrogen peroxide (30%, 1.7 g, 15 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-10 with a yield of 86%; HRMS (ESI) m / z:calcd for C 13 H 17 Cl 2 O 2 S[M+H] + 307.0321, found 307.0318.

[0069] Example 11: Preparation of Compound I-11

[0070] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 2,6-dichlorophenylmercaptan (1.78 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0071] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of acetonitrile, add hydrogen peroxide (30%, 1.7 g, 15 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-11 with a yield of 83%; HRMS (ESI) m / z:calcd for C 13 H 17 Cl 2 O 2 S[M+H] +307.0321, found 307.0320.

[0072] Example 12: Preparation of Compound I-12

[0073] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 2,6-difluorophenylthiol (1.46 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0074] Step 2: Compound IV obtained in step 1 was dissolved in 20 ml of acetonitrile, and hydrogen peroxide (30%, 1.7 g, 15 mmol) was added. After stirring at 25°C for 6 hours, the reaction solution was washed with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography (petroleum ether as eluent) to obtain compound I-12 with a yield of 85%; HRMS (ESI) m / z:calcd for C 13 H 17 F 2 O 2 S[M+H] + 275.0912, found 275.0911.

[0075] Example 13: Preparation of Compound I-13

[0076] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 4-pyridylthiol (1.11 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction bottle. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0077] Step 2: Dissolve the compound IV obtained in step 1 in 20 ml of acetonitrile, add hydrogen peroxide (30%, 1.7 g, 15 mmol), stir at 25°C for 6 hours, wash the reaction solution with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, then dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (petroleum ether as eluent) to obtain compound I-13, with a yield of 89%; HRMS (ESI) m / z:calcd for C12 H 18 NO 2 S[M+H] + 240.1053, found 240.1051.

[0078] Example 14: Preparation of Compound I-14

[0079] Step 1: Add 1-methylcyclohexyl chloride (Compound II) (0.66 g, 5 mmol), potassium tert-butoxide (1.12 g, 10 mmol), 2-thienyl mercaptan (1.15 g, 10 mmol) and 10 ml of N,N-dimethylacetamide into a reaction flask. After stirring at 25°C for 12 hours, add 30 ml of saturated brine to the reaction solution, extract with ethyl acetate (10 ml×3), concentrate the organic layer under reduced pressure, and separate and purify the concentrate by column chromatography (petroleum ether as eluent) to obtain Compound IV.

[0080] Step 2: Compound IV obtained in step 1 was dissolved in 20 ml of acetonitrile, and hydrogen peroxide (30%, 1.7 g, 15 mmol) was added. After stirring at 25°C for 6 hours, the reaction solution was washed with saturated sodium thiosulfate solution (10 ml) and saturated sodium bicarbonate solution (10 ml) in sequence, and then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography (petroleum ether as eluent) to obtain compound I-14 with a yield of 84%; HRMS (ESI) m / z:calcd for C 11 H 17 O 2 S 2 [M+H] + 245.0665,found245.0661.

[0081] Example 15: Test of herbicidal activity of compounds

[0082] 40-50 seeds of zinnia, velvetleaf, foxtail grass and barnyard grass were sown in a plastic pot with a diameter of 8 cm, covered with 1-2 mm of soil, and placed in an enamel dish filled with water to allow water to gradually penetrate. After the water seeped to the soil surface, the pot was transferred to a glass greenhouse for cultivation. When the weeds had 2-3 leaves, the seedlings were determined. 30 plants were determined in each pot. Water was regularly infiltrated from the bottom of the pot to maintain soil moisture. Each compound was set at 100 and 500 g ai / hm 2 Treatment. The test compound was dissolved in an appropriate amount of acetone, and then diluted to 500 mg / l with a 0.1% Tween-80 aqueous solution. The stems and leaves of the above-mentioned weeds were evenly sprayed at the 2-3 true leaf stage. The fresh weight of the above-ground part of each treated weed was weighed 20 days after the application, and the fresh weight control effect was calculated. The results are shown in Table 2.

[0083] Calculate the fresh weight control effect of each treatment according to the formula:

[0084] Inhibition rate / % = [fresh weight of control area - fresh weight of treatment area] / fresh weight of control area × 100

[0085] Table 2 Herbicidal activity of target compounds in potted plants (gai / hm 2 )

[0086]

Claims

1. A 1-methylcyclohexyl sulfone compound, characterized in that The compound has the structure shown in Formula I: Wherein: R substituent is selected from methyl, cyclopropyl, cyclohexyl, 4-chlorophenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 4-thiotrifluoromethylphenyl, 3-chlorophenyl, 3-fluorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 4-pyridyl or 2-thienyl.

2. The 1-methylcyclohexyl sulfone compound according to claim 1, characterized in that The R substituent is selected from 4-fluorophenyl, 3-chlorophenyl, 2,4-dichlorophenyl or 2,6-dichlorophenyl.

3. A method for preparing the 1-methylcyclohexyl sulfone compound according to claim 1 or 2, characterized in that: The synthetic route of this type of compound is as follows: The step 1: in a solvent, under the promotion of a base, compound II and compound III undergo a substitution reaction to obtain compound IV; The step 2: adding an oxidant to a solvent, and subjecting compound IV to an oxidation reaction to obtain 1-methylcyclohexyl sulfone compound I.

4. The preparation method according to claim 3, characterized in that: The 1-methylcyclohexyl halide II in step 1 is selected from any one of 1-methylcyclohexyl chloride, 1-methylcyclohexyl bromide or 1-methylcyclohexyl iodide.

5. The preparation method according to claim 3, characterized in that: The base in step 1 is selected from any one of potassium tert-butoxide, potassium carbonate, sodium carbonate or sodium ethoxide; the molar ratio of the base to compound II is (1.5-2):

1.

6. The preparation method according to claim 3, characterized in that: In the step 1, the molar ratio of compound II to compound III is 1:(1.5-2).

7. The preparation method according to claim 3, characterized in that: The solvent in step 1 is selected from any one of dimethyl sulfoxide, N,N-dimethylformamide or N,N-dimethylacetamide; the reaction temperature in step 1 is 25-80° C., and the reaction time is 12 hours.

8. The preparation method according to claim 3, characterized in that: The oxidant in step 2 is hydrogen peroxide; the molar ratio of the oxidant to compound II is (2-3):

1.

9. The preparation method according to claim 3, characterized in that: The solvent in step 2 is selected from any one of methanol, acetonitrile, or tetrahydrofuran; the reaction temperature is 25-50° C., and the reaction time is 4-6 hours.

10. Use of the 1-methylcyclohexyl sulfone compound according to claim 1 or 2 as a herbicide.

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