CN105601548A - Benzoyl compound, composition containing benzoyl compound and application of benzoyl compound - Google Patents

Abstract

The invention discloses a benzoyl compound having the following structural formula, a composition containing the compound and its application: Wherein, A, B, X and R are as defined in the specification. The benzoyl compounds provided by the invention have high growth inhibitory activity on various broad-leaved weeds and gramineous weeds, have no obvious phytotoxic effect on wheat, have good crop safety, and have few synthesis steps and a method It is simple and convenient, has low preparation cost and is suitable for large-scale industrial production.

Description

Benzoyl compounds, compositions containing the same and applications thereof

technical field

The invention belongs to the field of chemical herbicides, and in particular relates to benzoyl compounds, compositions containing the compounds and applications thereof.

Background technique

Existing studies have found that benzoyl compounds have herbicidal activity, and structural modifications and transformations have been carried out to obtain benzoyl compounds with better herbicidal activity and crop safety, simpler synthesis, and lower preparation costs. It is of great significance to develop the field of herbicides and reveal the structure-activity relationship of such herbicidally active compounds.

Contents of the invention

In order to overcome the above-mentioned problems, the present inventors studied benzoyl herbicides and their preparation methods diligently, and obtained benzoyl compounds with better herbicidal activity and crop safety and simpler preparation methods.

The object of the present invention is to provide the following aspects:

(1) Benzoyl compounds, whose structural formula is as shown in formula (I):

Wherein, A is selected from groups represented by formula (II) or formula (III);

In formula (III), Y ₁ , Y ₂ , and Y ₃ are selected from -H, alkyl, substituted alkyl, alkoxy, substituted alkoxy or hydroxyl;

B is selected from alkylsulfonyl;

X is selected from -H, alkyl, substituted alkyl, alkoxy, substituted alkoxy or halogen atoms;

R is selected from alkyl, substituted alkyl or groups containing at least one benzene ring.

(2) A production method comprising the compound described in (1) above.

(3) A composition containing the compound described in (1) above, wherein the composition further includes an emulsifier, a solubilizer, and a diluent.

(4) Use of the compound as described in (1) above as a herbicide, wherein the compound is used as a herbicide for suppressing emergence or growth of weeds in agricultural and forestry crops.

The beneficial effects that the present invention has include:

(1) The benzoyl compounds provided by the present invention can effectively inhibit the growth of roots and stems and albino seedlings of various plants at a dose of 100 mg/L, and the inhibition rate is 80-100%;

(2) The benzoyl compounds provided by the invention have higher growth inhibitory activity on various broad-leaved weeds and gramineous weeds at a dose of 150ga.i./ha, when the stems and leaves are sprayed after emergence, The inhibition rate is over 80%;

(3) The benzoyl compounds provided by the invention have no obvious phytotoxic effect on wheat at a dose of 150ga.i./ha, and have good crop safety;

(4) The benzoyl compound provided by the present invention has few synthesis steps, simple method and low preparation cost, and is suitable for large-scale industrial production.

Description of drawings

Fig. 1 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compounds that embodiment 1 makes;

Fig. 2 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compounds that embodiment 2 makes;

Fig. 3 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compounds that embodiment 3 makes;

Fig. 4 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compound that embodiment 4 makes;

Fig. 5 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compounds that embodiment 5 makes;

Fig. 6 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compounds that embodiment 6 makes;

Fig. 7 shows the proton nuclear magnetic resonance spectrogram of the benzoyl compound that embodiment 7 makes;

Figure 8 shows the H NMR spectrum of the benzoyl compounds prepared in Example 8.

detailed description

The present invention will be further described in detail through experimental examples and examples below. Through these descriptions, the features and advantages of the present invention will become more apparent.

According to the first aspect of the present invention, a benzoyl compound is provided, which has the structure shown in formula (I):

Wherein, A is selected from groups represented by formula (II) or formula (III);

In formula (III), Y ₁ , Y ₂ , and Y ₃ are selected from -H, alkyl, substituted alkyl, alkoxy, substituted alkoxy or hydroxyl;

B is selected from alkylsulfonyl;

X is selected from -H, alkyl, substituted alkyl, alkoxy, substituted alkoxy or halogen atoms;

R is selected from alkyl, substituted alkyl or groups containing at least one benzene ring.

In a preferred embodiment according to the present invention, the alkylsulfonyl group is selected from methylsulfonyl, ethylsulfonyl or propylsulfonyl, preferably methylsulfonyl or ethylsulfonyl, more preferably methyl Sulfonyl.

The alkyl group is selected from C ₁ -C ₁₀ alkyl groups, preferably C ₁ -C ₆ straight-chain alkyl groups, branched-chain alkyl groups or cycloalkyl groups, more preferably methyl, ethyl, n-propyl, Isopropyl or cyclopropyl, most preferably methyl or cyclopropyl.

The alkoxy group is selected from C ₁ -C ₁₀ alkoxy groups, preferably C ₁ -C ₆ alkoxy groups, more preferably methoxy, ethoxy or propoxy, most preferably methoxy .

The halogen atom is selected from F, Cl or Br, preferably F or Cl.

The substituted alkyl group is an alkyl group in which H is replaced by a halogen atom, preferably a C ₁ -C ₆ alkyl group containing 1 to 3 halogen atoms, more preferably a methyl group or an ethyl group containing 1 to 3 fluorine atoms or propyl, most preferably _-CF3 , _-CH2CHF2 (2,2 _- difluoroethyl) or _-CH2CF3 (2,2,2 _- trifluoroethyl).

The substituted alkoxy group is an alkoxy group in which H is replaced by a halogen atom, preferably a C ₁ to C ₆ alkoxy group containing 1 to 3 halogen atoms, more preferably a methoxy group containing 1 to 3 fluorine atoms radical, ethoxy or propoxy, most preferably F ₂ HCH ₂ CO-(2,2-difluoroethyl).

The group containing at least one benzene ring is preferably a phenyl group or a substituted phenyl group, and the substituted phenyl group is a phenyl group in which H is substituted by a substituted alkyl group, a nitro group or a halogen atom, wherein the substituted alkyl group is preferably It is a C ₁ -C ₆ alkyl group containing 1 to 3 halogen atoms, more preferably a methyl, ethyl or propyl group containing 1 to 3 fluorine atoms, most preferably -CF ₃ .

More preferably, the group containing at least one benzene ring is a phenyl group substituted by meta- or para-F, -NO ₂ or -CF ₃ .

Further preferably, in formula (I),

A is selected from the groups shown in the above formula (II) or formula (III), in formula (III), Y ₁ is hydroxyl, Y ₂ is methyl, Y ₃ is selected from methyl or cyclopropyl;

B is selected from methylsulfonyl;

X is -Cl;

R is selected from -CH ₂ CF ₃ , -CH ₂ CHF ₂ , or phenyl substituted by meta or para -F, -NO ₂ or -CF ₃ .

More preferably, the benzoyl compound has a structure shown in one of the following formulas (IV) to (XVIII):

Most preferably, the benzoyl compound has a structure as shown in formula (IV) or formula (IX):

According to the second aspect of the present invention, there is also provided a method for preparing benzoyl compounds shown in formula (I), which is prepared according to the following process flow:

Step (1) , the preparation of 2-substituted-6-methylthiotoluene: using water as a solvent, the raw material 3-substituted-2-methylaniline is first reacted with concentrated hydrochloric acid and sodium nitrite aqueous solution, and then sodium methylthiolate is added , sodium hydroxide and salt of wormwood react to obtain the product;

Step (2) , the preparation of 2-substituted-3-methyl-4-methylthioacetophenone: take dichloroethane as solvent, acetyl chloride and the 2-substituted-6-methanone prepared in step (1) Sulfuryltoluene is used as a raw material, and aluminum trichloride is used as a catalyst to carry out an acylation reaction to obtain the product;

Step (3) , the preparation of 2-substituted-3-methyl-4-methylsulfonyl acetophenone: take glacial acetic acid as solvent, hydrogen peroxide and the 2-substituted-3-methanone prepared in step (2) Base-4-methylthioacetophenone is used as raw material, and sodium tungstate is used as catalyst to carry out oxidation reaction to obtain 2-substituted-3-methyl-4-methylsulfonylacetophenone product;

Step (4) , the preparation of 2-substituted-3-methyl-4-methylsulfonylbenzoic acid: using dioxane as a solvent, the 2-substituted-3-methyl-4 prepared in step (3) - Oxidation of methylsulfonylacetophenone by sodium hypochlorite to generate said product;

Step (5) , the preparation of 2-substituted-3-methyl-4-methylsulfonylbenzoic acid methyl ester: under the catalysis of thionyl chloride, the 2-substituted-3-methyl prepared in step (4) -4-methylsulfonylbenzoic acid is esterified with methanol to obtain the product;

Step (6) , the preparation of 3-bromomethyl-2-substituted-4-methylsulfonylbenzoic acid methyl ester: with _CCl4 as solvent, under the catalysis of azobisisobutyronitrile, step (5) is prepared The bromination reaction of methyl 2-substituted-3-methyl-4-methylsulfonylbenzoate and NBS (N-bromosuccinimide) obtains the product;

Step (7) , the preparation of 2-substituted-3-substituted methyl-4-methylsulfonylbenzoic acid: using tetrahydrofuran as a solvent, under the catalysis of sodium hydride, alcohol or phenol containing R group and step (6) The bromine atom on the prepared 3-bromomethyl-2-substituted-4-methylsulfonylbenzoic acid methyl ester undergoes a substitution reaction to obtain the product;

Step (8) , the preparation of the target compound: using dichloroethane as a solvent, under the catalysis of thionyl chloride and acetone cyanohydrin, the 2-substituted-3-substituted methyl-4-methanol prepared in step (7) The substitution reaction between sulfonylbenzoic acid and 1,3-cyclohexanedione/1,3,5-substituted pyrazole produces the target compound.

According to the third aspect of the present invention, there is provided a composition containing the above-mentioned benzoyl compound, wherein the composition further includes an emulsifier, a co-solvent and a diluent.

The emulsifier is a Tween emulsifier, preferably Tween-60 or Tween-80, more preferably Tween-80.

The co-solvent is selected from N,N-dimethylformamide (DMF) or dimethyl sulfoxide (DMSO), preferably N,N-dimethylformamide.

The diluent is water, preferably distilled water.

In the composition, the weight ratio of the above-mentioned benzoyl compound, emulsifier and diluent is (0.01～20):(0.01～10):(50～200), preferably (0.1～15 ): (0.1-5): (70-150), more preferably (0.5-10): (0.5-2): (90-120).

Preferably, the composition is prepared according to the following method: mixing an emulsifier and a co-solvent, then adding the benzoyl compound to dissolve it, and then adding a diluent to prepare the required concentration.

According to the fourth aspect of the present invention, there is provided the use of the above-mentioned benzoyl compound as a herbicide, wherein the compound is used as a herbicide to inhibit the emergence or growth of weeds in agricultural and forestry crops.

The benzoyl compound can be used alone or in the form of a composition containing it as described above, so that it can directly contact the weed plant, or be applied to the soil where it grows or irrigation water to inhibit the emergence of weeds or grow.

Example

Example 1

According to the methods described in steps (1) to (8), the benzoyl compounds shown in the formula (IV) are prepared.

Step (1) , the preparation of 2-chloro-6-methylthiotoluene

In a 2L four-necked bottle with a condensing reflux device, add 200g (1.42mol) of 3-chloro-2-methylaniline, 380g (21mol) of water, and 425g (4mol) of concentrated hydrochloric acid, keeping the reaction temperature not exceeding 15 ℃, with the dropwise addition of hydrochloric acid, a white solid precipitates out. After the dropwise addition, continue to stir for 20 minutes, then cool down to 5°C, and dropwise add sodium nitrite aqueous solution (which contains NaNO ₂ 102g, H ₂ O 290g), keeping the reaction temperature not exceeding At 10°C, with the dropwise addition of sodium nitrite aqueous solution, the white solid gradually dissolves, and the reaction solution turns reddish brown. Continue stirring for 0.5h, and the reaction solution is ready for use;

In a 2L four-necked bottle with a condensing reflux device, add 20% sodium methyl mercaptide 600g (1.70mol), sodium hydroxide 56g (1.4mol), potassium carbonate 61g (0.45mol), stir until the solid is completely dissolved, drop Add the above-mentioned ready-to-use solution, keep the reaction temperature not exceeding 10°C, and continue the reaction for 24 hours after the dropwise addition is completed. After completion of the reaction, extract with 300 mL of dichloroethane, and evaporate the dichloroethane under reduced pressure to obtain 180 g of a yellow solution with a yield of 75.1% and a purity of 99.5%.

Step (2) , the preparation of 2-chloro-3-methyl-4-methylthioacetophenone

In a 500mL four-necked bottle with a reflux device, add 200mL of dichloroethane, 46g (0.35mol) of aluminum trichloride, 28g (0.35mol) of acetyl chloride, keep the reaction temperature not exceeding 20°C, and then dropwise add 2- Chloro-6-methylthiotoluene in dichloroethane solution (which contains 2-chloro-6-methylthiotoluene 51.6g, dichloroethane 200mL), keep the reaction temperature not exceeding 20 ° C, after the dropwise addition, Continue to react for 24h. After the reaction was completed, the reaction solution was added to a mixture of ice and concentrated hydrochloric acid, extracted with dichloroethane, washed with water, and evaporated to remove the solvent to obtain 62.8 g of a black liquid, with a yield of 103.1% (containing a small amount of dichloroethane), a purity of 97.1%.

Step (3) , the preparation of 2-chloro-3-methyl-4-methylsulfonylacetophenone

In a 500mL four-necked bottle with a reflux device, add 64.2g (0.3mol) of 2-chloro-3-methyl-4-methylthioacetophenone, 300mL of glacial acetic acid, 1g of sodium tungstate, and then dropwise add 30% 70g (0.62mol) of hydrogen peroxide was heated to 80°C and kept for 1 hour. After the reaction, suction filtration, washing with water and drying gave 68.6g of white solid with a yield of 93.2% and a purity of 97.0%.

Step (4) , the preparation of 2-chloro-3-methyl-4-methylsulfonylbenzoic acid

In a 1L four-necked bottle with a reflux device, add 300 mL of dioxane, 24.6 g (0.1 mol) of 2-chloro-3-methyl-4-methylsulfonyl acetophenone, and dropwise add 466 g of 10% sodium hypochlorite (0.63mol), heated to 80°C, and kept the temperature for 2h. After the reaction of the raw material 2-chloro-3-methyl-4-methylsulfonylacetophenone was completed, the solvent was evaporated under reduced pressure, and then the temperature was lowered to 40°C. Hydrochloric acid was added dropwise to adjust the pH to 2, filtered and dried to obtain 23.56 g of a white solid with a yield of 95.0% and a purity of 98.6%.

Step (5) , the preparation of 2-chloro-3-methyl-4-methylsulfonylbenzoic acid methyl ester

In a 500mL four-necked bottle with a reflux device, first add 200mL of methanol, 24.6g (0.1mol) of 2-chloro-3-methyl-4-methylsulfonylbenzoic acid, 5.9g (0.05mol) of thionyl chloride ), control the reaction temperature not to exceed 25°C, and raise the temperature to reflux for 2h. After the reaction was completed, it was cooled down to room temperature, and 23.37 g of solid was obtained after suction filtration and drying, with a yield of 93.4% and a purity of 98.0%.

Step (6) , the preparation of 3-bromomethyl-2-chloro-4-methylsulfonylbenzoic acid methyl ester

In a 500mL four-necked bottle with a reflux device, add 400mL of CCl ₄ , 52.4g (0.2mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate, 0.20 of azobisisobutyronitrile g, then add NBS39.16g (0.2mol) in 5 times, raise the temperature to reflux, and keep the reflux reaction for 8h. , and dried to obtain 51.1 g of a yellow solid, with a yield of 75.2% and a purity of 95.5%.

Step (7) , the preparation of 2-chloro-3-(4-nitrophenoxy)methyl-4-methylsulfonylbenzoic acid

In a 500mL four-necked bottle with a reflux device, add 200mL of tetrahydrofuran and 4g of sodium hydride, control the reaction temperature not to exceed 20°C, and add dropwise a tetrahydrofuran solution of p-nitrophenol (containing 16.68g of p-nitrophenol and 100mL of tetrahydrofuran) , stirred for 0.5h after the dropwise addition, added 34g (0.1mol) of the intermediate 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate, reacted at room temperature for 4h, then added sodium hydroxide 4.8 g (0.12mol), water 200mL, after heating and refluxing for 2h, cool to 20°C, add hydrochloric acid dropwise to adjust the pH to 2. Suction filtration and drying yielded 35.42 g of a white solid with a yield of 92.0% and a purity of 97.0%.

Step (8) , preparation of target compound

In a 250mL four-necked bottle with a reflux device, add 200mL of dichloroethane, 7.7g of 2-chloro-3-(4-nitrophenoxy)methyl-4-methylsulfonylbenzoic acid (0.02mol ), 2.856g (0.024mol) of thionyl chloride, the reaction temperature is controlled not to exceed 20°C, after the dropwise addition is completed, the temperature is raised to reflux reaction for 1h, after the reaction is completed, dichloroethane and thionyl chloride are distilled off under reduced pressure The solution is ready for use;

In a 250mL four-necked bottle with a reflux device, add 200mL of dichloroethane, 2.69g (0.024mol) of 1,3-cyclohexanedione, 6g (0.06mol) of triethylamine, and control the reaction temperature not to exceed 20°C , dropwise add the above-mentioned ready-to-use solution, control the reaction temperature not to exceed 35°C, after the reaction is completed, add 0.5mL of acetone cyanohydrin dropwise, and continue the reaction for 24h. Add 100mL of water, add hydrochloric acid to adjust the pH to 2, separate liquid, wash with water, evaporate dichloroethane under reduced pressure, add 80mL of methanol, stir to precipitate solid, filter with suction and dry to obtain 8.74g of product, yield 91.2%, purity 97.1%, its H NMR spectrum is shown in Figure 1.

Example 2

Prepare according to a method similar to Example 1, the only difference is that the p-nitrophenol in step (7) is replaced by 9.84g of 2,2-difluoroethanol to obtain benzoyl as shown in formula (V) compounds, and their H NMR spectra are shown in Figure 2.

Example 3

Prepare according to a method similar to Example 1, the only difference is that the 1,3-cyclohexanedione in step (8) is replaced by an equivalent amount of 1,3-dimethyl-5-pyrazolone to obtain The H NMR spectrum of the benzoyl compound shown in formula (VI) is shown in FIG. 3 .

Example 4

Prepare according to a method similar to Example 1, the only difference is: replace 1,3-cyclohexanedione in step (8) with 3.31 g of 1-methyl-3-cyclopropyl-5-pyrazolone (0.024mol) to obtain the benzoyl compounds shown in formula (VII), the H NMR spectrum of which is shown in Figure 4.

Example 5

Prepare according to the method similar to Example 1, the only difference is: the p-nitrophenol in the step (7) is replaced by 13.44g of 4-fluorophenol, to obtain the benzoyl compounds shown in formula (Ⅷ), Its H NMR spectrum is shown in Figure 5.

Example 6

Prepare according to a method similar to Example 1, the only difference is: the p-nitrophenol in step (7) is replaced by m-trifluoromethylphenol 19.44g to obtain benzoyls as shown in formula (IX) Compound, its H NMR spectrum is shown in Figure 6.

Example 7

Prepare according to a method similar to Example 1, the only difference is: the p-nitrophenol in step (7) is replaced by m-trifluoromethylphenol 19.44g, and the 1,3-cyclohexyl in step (8) The diketone is replaced by an equivalent amount of 1,3-dimethyl-5-pyrazolone to obtain a benzoyl compound as shown in formula (X), and its H NMR spectrum is shown in FIG. 7 .

Example 8

Prepare according to a method similar to Example 1, the only difference is: the p-nitrophenol in step (7) is replaced by m-trifluoromethylphenol 19.44g, and the 1,3-cyclohexyl in step (8) Diketone is replaced by 1-methyl-3-cyclopropyl-5-pyrazolone 3.31g (0.024mol), obtains the benzoyl compound as shown in formula (XI), and its H-NMR spectrum is shown in the figure 8.

Experimental example

The biological activity of the benzoyl compounds prepared in Examples 1-8 was measured according to the method described in Experimental Examples 1-3, as follows.

Experimental example 1 Herbicidal activity test-plate method

(1) Sample preparation

Use an analytical balance (0.0001g) to weigh a certain amount of benzoyl compounds prepared in Examples 1 to 8, and dissolve them in N,N-dimethylformamide (DMF) containing 1% Tween-80 to prepare 1.0-5.0% mother liquor, then dilute with distilled water for later use.

(2) Test method

The test targets are radish, cucumber, rapeseed, wheat, sorghum and barnyard grass, among which the seeds of wheat, sorghum and radish are germinated in advance, and the uniform white seeds are taken for the test. Add 9ml of each benzoyl compound solution with a concentration of 100mg/L to the dish, as the treatment group, use the same dose of mesotrione as the positive control, and use the same amount of sterile distilled water as the blank control; Mark, place in an artificial climate box for cultivation, set the temperature at 28°C; light 3000Lux, light time according to 16h light, 8h dark cycle, relative humidity (RH) 75%, investigate the growth of roots and stems after 7 days, and press the formula Calculate the root and stem growth inhibition rate (%) of the compound provided by the invention to the target plant, and the results are shown in Table 1.

Root growth inhibition rate (%)=(root growth amount of blank control group-root growth amount of treatment group)/root growth amount of blank control group×100%

Stem growth inhibition rate (%)=(blank control group stem growth amount-treatment group stem growth amount)/blank control group stem growth amount×100%

Table 1. Herbicidal activity dish test results of compounds

As shown in Table 1, the benzoyl compounds prepared in Examples 1 to 8 of the present invention have higher activity to radish, cucumber, rape, wheat, sorghum and barnyardgrass at a treatment dose of 100 mg/L. The stem growth inhibition rate is 80-100%, manifested as inhibition of root and stem growth and seedling albinism, and the symptoms are similar to those of the positive control mesotrione.

Experimental Example 2 Herbicidal Activity Test-Pot Planting Method

(1) Sample preparation

Use an analytical balance (0.0001g) to weigh a certain amount of benzoyl compounds prepared in Examples 1 to 8, and dissolve them in N,N-dimethylformamide (DMF) containing 1% Tween-80 to prepare 1.0-5.0% mother liquor, then dilute with distilled water for later use.

(2) Test method

The targets for the test are winter weeds mustard, bluegrass, chickweed, argonopsis, quinoa and clubhead grass. Take a flowerpot with an inner diameter of 7.5 cm and fill it with compound soil (vegetable garden soil: seedling substrate (v:v) = 1: 2) To the 3/4 place, directly sow the above-mentioned weed targets (bud rate ≥ 85%), cover with 0.2 cm of soil, and wait for the weeds to grow to about 3 leaf stage for later use. The samples of each compound were sprayed at a dose of 150ga.i./ha by an automatic spray tower (model: 3WPSH-700E), and the same amount of sterile distilled water was applied as a blank control. Cultivate, investigate the inhibitory activity of the compound on weeds after 25 days, investigate the herbicidal activity of the compound according to the ten-level visual method (0 level = no obvious reaction, 10 level = plant is completely dead), and the visual observation data is converted into the treatment of weed plants relative to the blank The biomass inhibition percentage of the control (eg 1.5 level=15%) is the growth inhibition rate of the compound on weeds, and the results are shown in Table 2.

Table 2. Pot herbicidal activity test results of compounds

As shown in Table 2, the benzoyl compounds prepared in Examples 1 and 2 of the present invention have higher activity to the 6 kinds of weed targets tested under the dosage of 150 ga.i./ha, and when the stems and leaves are sprayed after emergence 7-10 days after spraying, the leaves of the weeds will be albino and withered, especially the heart leaves will be albino, and the whole plant will die. After 25 days, all the weed plants will die, and the growth inhibition rate is 100%.

Experimental Example 3 Crop Safety Test

(1) Sample preparation

Weigh a certain mass of benzoyl compounds prepared in Examples 1 to 6 with an analytical balance (0.0001g), and dissolve them in N,N-dimethylformamide (DMF) containing 1% Tween-80 to prepare 1.0-5.0% mother liquor, then dilute with distilled water for later use.

(2) Test method

The test targets are wheat and rapeseed. Take a flowerpot with an inner diameter of 12cm, fill it with compound soil (vegetable garden soil: seedling substrate (v:v) = 1:2) to 3/4, and directly sow the seeds of the above crops (germination rate ≥ 85% ), cover the soil with 0.2cm, and wait for the plant to grow to about 3 to 4 leaves for later use. Each compound was sprayed by an automatic spray tower according to the dose of 150ga.i./ha, and an equal amount of sterile distilled water was applied as a blank control. Dark) culture, continuous visual observation of the crop response, 20 days after the investigation test results, and according to the formula to calculate the compound's fresh weight inhibition rate of the target plant, the results are shown in Table 3.

Inhibition rate of fresh weight=(fresh weight of aboveground parts of plants in blank control group-fresh weight of aboveground parts of plants in treatment group)/fresh weight of aboveground parts of plants in blank control group×100%

Table 3. Potted crop safety test results of compounds

As shown in Table 3, after the post-emergence stem and leaf treatment at a dose of 150ga.i./ha, the benzoyl compounds prepared in Examples 1 to 6 of the present invention all had obvious phytotoxicity to rapeseed. ～10 days cause the albinism of plant leaves, especially more serious with heart leaf, and then can not grow normally and whole plant dies, and above-mentioned 6 compounds all are more than 40% to the fresh weight inhibition rate of above-ground part of rape, all unsafe; Embodiment 3, The inhibition rates of the compounds prepared in 4 and 6 on the fresh weight of above-ground parts of wheat were all less than 10%, which was relatively safe to wheat.

The present invention has been described in detail above with reference to preferred embodiments and illustrative examples. However, it should be declared that these specific embodiments are only illustrative explanations of the present invention, and do not constitute any limitation to the protection scope of the present invention. Without departing from the spirit and protection scope of the present invention, various improvements, equivalent replacements or modifications can be made to the technical contents and implementation methods of the present invention, all of which fall within the protection scope of the present invention. The protection scope of the present invention shall be determined by the appended claims.

Claims (10)

1. Benzoyl compound is characterized in that, its structural formula is as shown in formula (I): in, A is selected from groups represented by formula (II) or formula (III); In formula (III), Y ₁ , Y ₂ , and Y ₃ are selected from -H, alkyl, substituted alkyl, alkoxy, substituted alkoxy or hydroxyl; B is selected from alkylsulfonyl; X is selected from -H, alkyl, substituted alkyl, alkoxy, substituted alkoxy or halogen atoms; R is selected from alkyl, substituted alkyl or groups containing at least one benzene ring. 2. The compound according to claim 1, wherein the alkylsulfonyl group is selected from methylsulfonyl, ethylsulfonyl or propylsulfonyl, and/or The alkyl group is selected from C ₁ -C ₁₀ alkyl groups, preferably C ₁ -C ₆ straight-chain alkyl groups, branched-chain alkyl groups or cycloalkyl groups, more preferably methyl, ethyl, n-propyl, isopropyl or cyclopropyl, and/or The alkoxy group is selected from C ₁ -C ₁₀ alkoxy groups, preferably C ₁ -C ₆ alkoxy groups, more preferably methoxy, ethoxy or propoxy, and/or The halogen atom is selected from F, Cl or Br, preferably F or Cl. 3. The compound according to claim 1 or 2, characterized in that, The substituted alkyl group is an alkyl group in which H is replaced by a halogen atom, preferably a C ₁ -C ₆ alkyl group containing 1 to 3 halogen atoms, and/or The substituted alkoxy group is an alkoxy group in which H is replaced by a halogen atom, preferably a C ₁ -C ₆ alkoxy group containing 1 to 3 halogen atoms, and/or The group containing at least one benzene ring is preferably a phenyl group or a substituted phenyl group, and the substituted phenyl group is a phenyl group in which H is substituted by a substituted alkyl group, a nitro group or a halogen atom, wherein the substituted alkyl group is preferably It is a C ₁ -C ₆ alkyl group containing 1 - 3 halogen atoms. 4. The compound according to any one of claims 1 to 3, characterized in that B is selected from methylsulfonyl; and/or X is -Cl; and/or R is selected from -CH ₂ CF ₃ , -CH ₂ CHF ₂ or phenyl substituted by -CF ₃ , nitro or -F; and/or In formula (III), Y ₁ is hydroxyl, Y ₂ is methyl, and Y ₃ is selected from methyl or cyclopropyl. 5. The compound according to any one of claims 1 to 4, wherein the compound has the following structure: 6. The compound according to any one of claims 1 to 5, characterized in that the compound has a structure as shown in formula (IV) or formula (IX): 7. according to the preparation method of the benzoyl compound described in one of claims 1 to 6, it is characterized in that, comprising the following steps: Step (1) , 3-substituted-2-methylaniline reacts with concentrated hydrochloric acid and sodium nitrite aqueous solution, then adds sodium methyl mercaptide, sodium hydroxide and potassium carbonate to react to obtain 2-substituted-6-methylthio Toluene; In step (2) , acetyl chloride is acylated with 2-substituted-6-methylthiotoluene prepared in step (1) to obtain 2-substituted-3-methyl-4-methylthioacetophenone; In step (3) , hydrogen peroxide is oxidized with the 2-substituted-3-methyl-4-methylthioacetophenone prepared in step (2) to obtain 2-substituted-3-methyl-4-methyl Sulfonylacetophenone; Step (4) , the 2-substituted-3-methyl-4-methylsulfonyl acetophenone obtained in step (3) is oxidized by sodium hypochlorite to generate 2-substituted-3-methyl-4-methylsulfonyl benzoic acid; Step (5) , the 2-substituted-3-methyl-4-methylsulfonylbenzoic acid prepared in step (4) is esterified with methanol to obtain 2-substituted-3-methyl-4-methyl Methyl sulfonylbenzoate; Step (6) , 2-substituted-3-methyl-4-methylsulfonylbenzoic acid methyl ester prepared in step (5) is brominated with NBS to obtain 3-bromomethyl-2-substituted-4 - methyl methylsulfonylbenzoate; In step (7) , the bromine atom on the alcohol or phenol containing the R group and the bromine atom on the 3-bromomethyl-2-substituted-4-methylsulfonylbenzoic acid methyl ester prepared in step (6) is subjected to a substitution reaction to obtain 2-substituted-3-substituted methyl-4-methylsulfonylbenzoic acid; Step (8) , 2-substituted-3-substituted methyl-4-methylsulfonylbenzoic acid prepared in step (7) is carried out with 1,3-cyclohexanedione or 1,3,5-substituted pyrazole The substitution reaction produces the target compound. 8. The composition containing the compound according to any one of claims 1 to 6, characterized in that the composition further comprises emulsifiers, co-solvents and diluents. 9. The composition according to claim 8, characterized in that, The emulsifier is a Tween emulsifier, preferably Tween-60 or Tween-80, and/or The cosolvent is selected from N,N-dimethylformamide or dimethylsulfoxide, and/or The diluent is water, and/or The weight ratio of the compound, emulsifier and diluent as claimed in one of claims 1 to 6 is (0.01～20): (0.01～10): (50～200), preferably (0.1～15): (0.1 -5): (70-150), more preferably (0.5-10): (0.5-2): (90-120). 10. The use of the compound according to one of claims 1 to 6 as a herbicide, characterized in that the compound is used as a herbicide to inhibit the emergence or growth of weeds in agricultural and forestry crops, preferably as claimed in any one of claims 1 to 6 A said compound or a composition as claimed in claim 8 or 9 is directly contacted with weed plants, or applied to its growing soil or irrigation water to inhibit the emergence or growth of weeds.