CN104725288A - Benzophenone hydrazone sulfonylurea compound and its preparation method and use - Google Patents

Abstract

The present invention relates to a new benzophenone hydrazone sulfonylurea compound represented by formula ( I ), as well as the preparation method of this compound and its use in the preparation of insecticides and acaricides. ( I )

Description

A kind of benzophenone hydrazone sulfonylurea compound and its preparation method and application

technical field

The invention relates to a novel benzophenone hydrazone sulfonylurea compound, a preparation method of the compound, and an application thereof in preparing insecticides and acaricides. the

Background technique

In 1973, the DuPont Company of the United States reported for the first time the excellent insecticidal activity of some benzophenone hydrazone compounds with simple structures (Middleton WJ, Chadds F, (DuPont). US3732307). With the characteristics of broad spectrum and low toxicity, this kind of compound has attracted the interest of many pesticide companies and scientific researchers. BASF, Sumitomo, DuPont, Bayer and other foreign companies have successively reported a large number of derivatives of benzophenone hydrazone structure with pesticide biological activity, and have successively developed commercial varieties such as insecticide hydrazone and metaflumizone, Widely used in agricultural production ((1) Kang Shenghong, et al. Pesticides, 2012, 51, 238-242; (2) Wu Xia et al., Modern Pesticides, 2004, 3, 32-35). At the same time, the benzophenone hydrazone derivative mesyflumizone developed by Zhejiang Research Institute of Chemical Industry has shown high-efficiency insecticidal activity against lepidopteran pests, and is expected to become a new type of pesticide insecticide (Xing Jiahua et al., Journal of Pesticide Science, 2008, 10, 236-239). In recent years, there have been many relevant literature or patent reports on the modification and transformation of benzophenone hydrazone derivatives, and many highly active compounds have been discovered. For example, in 1993, Novartis reported a series of benzophenone acylhydrazone derivatives (Formula I), and found that they had better activity against armyworm, Spodoptera litura, and Spodoptera (Duerr DD, Hall DREP0662472).

In 1995, Sumitomo Corporation of Japan synthesized a series of diacylbenzophenone hydrazone derivatives (Formula II), and found that these compounds had better insecticidal activity against Lepidoptera pests (Sumitomo Chemical Industry Co., Ltd. JP7149708).

In 1998, Bayer Company designed and synthesized a class of benzophenone hydrazone derivatives (Formula III), and found that it not only has high activity against Lepidoptera insects, but also has certain activity against mites (Kitagawa Yoshizawa et al. JP10182625). the

Later, Japan Otsuka discovered a series of sulfonyl benzophenone hydrazone derivatives (Formula IV), which have a 100% lethality to armyworms at a concentration of 10mg/L (Daisheng Chemical Co., Ltd. JP10109971).

In 2000, Japanese Agro-Kanesho Company designed and synthesized a dicarbonylbenzophenone hydrazone derivative (Formula V), and found that it has broad-spectrum insecticidal activity against Lepidoptera insects (Usui S, et al. WO0023422).

In addition, on the basis of the research on the structure-activity relationship of benzophenone hydrazone derivatives, domestic scholars have also successively reported benzophenone hydrazone derivatives such as acylhydrazone, semicarbazone, thiosemicarbazone, and dihydrazone (Zheng Yuguo et al., Guangzhou Chemical Industry, 2012, 40, 1-3). the

The present invention summarizes its structure-activity relationship on the basis of existing patents or compounds reported in literature, and finds that when the para-position of the A ring is substituted by a halogen and the para-position of the B ring is substituted by a trifluoromethanesulfonate group, the activity is the highest, and the hydrazone The upper amino group is the best modification position, and it is worthy of further modification and optimized synthesis. Accordingly, the present invention introduces a sulfonylurea structure on the hydrazone nitrogen atom on the basis of retaining the active basic skeleton, and changes the type of substituent to synthesize A new class of benzophenone hydrazonesulfonylurea derivatives was obtained. But so far, there are no research reports on the use of benzophenone hydrazone as a leading structure and the application of sulfonylurea active functional groups for structural modification and the insecticidal and acaricidal activities of such compounds. the

Contents of the invention

The technical scheme of the present invention is based on the advantages that benzophenone hydrazone compounds have excellent insecticidal activity, and sulfonylurea active functional groups have extensive biological activity, etc., and can improve the biological activity of some lead molecules. Therefore, on the basis of analyzing the structure-activity relationship, the present invention introduces a sulfonylurea structure on the hydrazone nitrogen atom, and changes the type of substituents to synthesize a new class of benzophenone hydrazone sulfonylurea derivatives, which are expected to Improve its biological activity through this structural optimization. the

In order to develop a new benzophenone hydrazone derivatives with insecticidal and acaricidal activities, the present invention has been carefully investigated and researched, and as a result, it has been found that the compound represented by the general formula (VI) has neither been disclosed nor disclosed in the prior art. It is not suggested, it is a new compound that has not been found in any publications, and this type of compound shows excellent poisonous activity against Tetranychus cinnabarinus and bean aphid, thus completing the present invention.

Wherein (I) R is methyl, 2-naphthyl, phenyl, p-fluorophenyl, p-chlorophenyl, p-methylphenyl, 2,4-methoxyphenyl or 2,4-fluoro phenyl. the

The benzophenone hydrazone parent material involved in the present invention is according to the existing literature ((1) Ducharme Y, et al.J.Med.Chem.1994,37,512-518; (2) Bourget C, et al.Bioorg.Med.Chem .2005,13,1453-1456; (3) Xia Xujian, etc., Chinese patent, application number: 01119493.6) The preparation method is completed, that is, at first 4-chlorobenzoyl chloride and phenol are dissolved in dichloroethane solution, in Under the action of anhydrous aluminum chloride, carry out Friedel-Crafts acylation reaction to obtain the intermediate 4-chloro-4-hydroxybenzophenone (3), and then use pyridine as an acid-binding agent in a dry dichloromethane solvent to make the intermediate Body 3 and trifluorosulfonic anhydride react to obtain intermediate 4-chloro-4'-trifluoromethanesulfonate base benzophenone (4), and then intermediate 4 and hydrazine hydrate are catalyzed by a small amount of acetic acid in methanol solution The benzophenone hydrazone parent material (5) is obtained through condensation, and its reaction is shown in Reaction Formula 2. the

The preparation method of raw material ethyl sulfonylcarbamate used in the present invention is referring to literature method (Xi PX, Xu ZH, Liu XH, et al.J Fluoresc, 2009,19,63-72. and Xi PX, Xu ZH, Liu XH , et al.Chem.Pharm.Bull.(Tokyo), 2008,56,541-546.), that is, to condense differently substituted sulfonyl chlorides with 28% ammonia water to obtain the corresponding sulfonamide, which is dissolved in anhydrous acetone without separation Add anhydrous K ₂ CO ₃ , and reflux to obtain raw material ethyl sulfonylcarbamate.

The preparation method of the target compound of the present invention, benzophenone hydrazone sulfonylurea compound (6a-h), is carried out according to the following chemical reaction formula 1, that is: under the protection of nitrogen, the reaction temperature is from room temperature to the reflux temperature of the selected solvent, and It is obtained by reacting in a solvent using the reaction equation shown in general formula 1 for 2-10 hours. the

As the solvent used for this reaction, the solvents that can be selected have benzene, toluene, tetrahydrofuran, dimethyl sulfoxide, acetone, dichloromethane, N,N-dimethylformamide; these solvents are used alone or in combination, Preferred toluene when used as the solvent used alone in the reaction; when used as a mixed solvent, its mixing ratio can be: 1～5:100. the

The reaction temperature is from room temperature to the reflux temperature of the selected solvent, preferably the temperature is the reflux temperature of the selected solvent. the

The reaction time is usually selected from 2 to 10 hours, preferably from 2 to 6 hours. the

After the reaction is completed, the desired compound is separated from the reaction mixture by a common method, that is, a silica gel column with 200 to 300 meshes is used for chromatography, and the eluent is petroleum ether: the volume ratio of acetone is 10 :1～20:1 to obtain pure target compounds, and the structures of all final compounds were confirmed by mass spectrometry and NMR. the

The present invention has carried out the poisonous killing activity test to spider mite cinnabarinus, bean aphid to all target compounds, and the result shows, the compound of formula 1 shows stronger poisonous killing activity to it, so compound of the present invention can be used for preparing insecticidal, Acaricide. The compound described in the invention has novel structure, simple synthesis process, high product purity, strong poisonous effect on test insects, and excellent application prospect. the

The above-mentioned content of the present invention will be further described in detail below through specific embodiments. However, this should not be construed as limiting the invention. the

Detailed ways

Example 1

Synthesis of N-methylsulfonyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-keto]semicarbazone (6a)

Synthesis of raw material benzophenone hydrazone precursor (5): Dissolve 0.1mmol of phenol in 100mL of dry dichloroethane, quickly weigh and add 1.5mmol of anhydrous aluminum trichloride, heat to about 70°C in an oil bath, 0.1 mmol of 4-chlorobenzoyl chloride was added dropwise to the reaction liquid, and stirring was continued for 2 hours after the dropwise addition was completed. Cooled, poured into 100mL of ice water, extracted three times with dichloromethane, separated the organic phase, dried with anhydrous sodium sulfate, evaporated the solvent under reduced pressure, and recrystallized with anhydrous methanol to obtain 4-chloro-4- Hydroxybenzophenones (3). Dissolve 0.05mmol of 4-chloro-4-hydroxybenzophenone in 50mL of dry dichloromethane, drop into 0.05mL of pyridine, control the temperature at 0°C, add 0.06mmol of trifluoromethanesulfonic anhydride dropwise, stir at room temperature for 3 hours, then stop Reaction, washed directly with water (3×50mL), after extraction, the organic layer was dried with anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain a light yellow oil, which was purified by column chromatography (petroleum ether: ethyl acetate) to obtain 4- Chloro-4'-trifluoromethanesulfonate benzophenone (4), yield 96%. the

Further, dissolve 4-chloro-4'-trifluoromethanesulfonate benzophenone in 30mL of absolute ethanol, add 0.5mL of acetic acid dropwise, add 0.3mL of hydrazine hydrate dropwise, heat to reflux and stir for 12 hours, then stop After reaction, the solvent was evaporated to obtain a yellow oil, which was dissolved by adding 20 mL of dichloromethane, washed with water (2×20 mL), and after extraction, the organic layer was taken and dried with anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to obtain a colorless oil. Place overnight to obtain the white needle-like crystal benzophenone hydrazone precursor (5), the yield is 90%, and its reaction

Synthesis of raw material ethyl methylsulfonyl carbamate: put methanesulfonyl chloride (3mmol) in a round-bottomed flask, slowly add 28% ammonia water (12mmol) dropwise, after the dropwise addition, stir at room temperature for 4 hours, and then heat under reflux Cool to room temperature until the release of ammonia gas is complete, and a white solid is obtained which is methylsulfonamide. The methylsulfonamide obtained by the reaction was dissolved in acetone and spin-dried, and the process was repeated 3 to 5 times, and the water contained in the compound could be spin-dried for use in the next step. Dissolve the methylsulfonamide (2.5mmol) obtained in the previous step in dry acetone, add powdered anhydrous K ₂ CO ₃ (6.5mmol) to the reaction flask, heat to reflux, stir for 30 minutes, and then dissolve the chlorine Ethyl formate (3.3 mmol) was added to a small amount of dry acetone, ethyl chloroformate-acetone solution was added dropwise to the reaction solution with a constant pressure funnel, and heated to reflux for 4 hours. After the reaction, pour the reaction solution into a small amount of distilled water to dissolve the unreacted _K2CO3 , then adjust it to weak acidity with 1M _HCl solution, extract with ethyl acetate, combine the organic phases, and _wash with anhydrous _Na2SO4 After drying, filter and distill off the solvent under reduced pressure. The obtained solid or oily product is subjected to column chromatography to obtain the intermediate product ethyl methylsulfonylcarbamate. For the method used, refer to literature methods (Xi PX, Xu ZH, Liu XH, et al.J Fluoresc, 2009, 19, 63-72. and Xi PX, Xu ZH, Liu XH, et al.Chem.Pharm.Bull.(Tokyo ), 2008, 56, 541-546.)

Its reaction sees reaction formula 3

Dissolve 1mmol of ethyl methylsulfonylcarbamate in 10mL of toluene, heat to boiling, under the protection of nitrogen, dissolve 2mmol of benzophenone hydrazone precursor in 10mL of toluene, add dropwise to the reaction solution, heat to reflux for 2 hours, and react After completion, after the solvent was evaporated under reduced pressure, the crude product was purified by column chromatography (elution system was petroleum ether: acetone: 20:1), and the compound N-methylsulfonyl-[(4-chloro Phenyl)(4-trifluoromethylsulfonylphenyl)-keto]semicarbazone (6a). the

The detection data of the product obtained from the reaction are as follows: Yield: 45%; Melting point: 201-203°C; ¹ H NMR (400MHz, CDCl ₃ ) δ: 3.22(s, 3H, -CH ₃ ), 7.42(d, J=8.8Hz ,2H,Ar-H),7.50(d,J=8.4Hz,2H,Ar-H),7.75(d,J=8.4Hz,2H,Ar-H),7.83(d,J=8.8Hz,2H ,Ar-H),8.29(s,1H,-CONHSO ₂ -); MS-ESI m/z:500.2[M+H] ⁺ .

Example 2

Synthesis of N-naphthalenesulfonyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6b)

The experimental procedure is the same as in Example 1, except that methyl is replaced by naphthyl. The detection data of the product obtained from the reaction are as follows: Yield: 55%; Melting point: 198-200°C; ¹ H NMR (400MHz, DMSO-d ₆ ) δ: 7.21 (d, J=8.4Hz, 1H, Ar-H), 7.27 (d,J=8.0Hz,1H,Ar-H),7.39-7.47(m,4H,Ar-H),7.59(d,J=8.4Hz,2H,Ar-H),7.65-7.74(m, 3H,Ar-H),7.91(d,J=8.8Hz,1H,Ar-H),8.05(d,J=7.2Hz,1H,Ar-H),8.14(d,J=8.8Hz,1H, Ar-H),8.23(d,J=8.0Hz,1H,Ar-H),9.55(s,1H,-CONHSO ₂ -);MS-ESI m/z:612.3[M+H] ⁺ .

Example 3

Synthesis of N-p-fluorobenzoyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6c)

The experimental procedure is the same as in Example 1, except that p-fluorophenyl is used instead of methyl. The detection data of the product obtained from the reaction are as follows: Yield: 48%; Melting point: 209-210°C; ¹ H NMR (400MHz, DMSO-d ₆ ) δ: 7.21 (d, J=8.4Hz, 1H, Ar-H), 7.29 (d,J=8.4Hz,1H,Ar-H),7.37-7.50(m,7H,Ar-H),7.59(d,J=8.4Hz,1H,Ar-H),7.66(d,J= 8.4Hz,1H,Ar-H),7.91-7.97(m,1H,Ar-H),9.24(s,1H,-CONHSO ₂ -); MS-ESI m/z:579.9[M+H] ⁺ .

Example 4

Synthesis of N-p-chlorobenzoyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6d)

The experimental procedure is the same as in Example 1, except that methyl is replaced by p-chlorophenyl. The detection data of the product obtained from the reaction are as follows: Yield: 51%; Melting point: 205-207°C; ¹ H NMR (400MHz, DMSO-d ₆ ) δ: 6.90-7.02(dd, J ₁ =8.4Hz, J ₂ =40.0Hz ,4H,Ar-H),7.10-7.22(dd,J ₁ =8.0Hz,J ₂ =40.4Hz,4H,Ar-H),7.31-7.32(m,2H,Ar-H),7.57(d, J=8.4Hz,2H,Ar-H),9.73(s,1H,-CONHSO ₂ -); MS-ESI m/z:596.4[M+H] ⁺ .

Example 5

Synthesis of N-benzoyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-keto]semicarbazone (6e)

The experimental procedure is the same as in Example 1, except that methyl is replaced by phenyl. The detection data of the product obtained from the reaction are as follows: Yield: 57%; Melting point: 211-223°C; ¹ HNMR (400MHz, CDCl ₃ ) δ: 7.19 (d, J=8.4Hz, 2H, Ar-H), 7.25-7.28( m,1H,Ar-H),7.36(d,J=8.4Hz,2H,Ar-H),7.42(d,J=8.4Hz,2H,Ar-H),7.50(d,J=8.4Hz, 2H, Ar-H), 7.57-7.63 (dd, J ₁ =8.4Hz, J ₂ =16.8Hz, 4H, Ar-H), 8.32 (s, 1H, -CONHSO ₂ -); MS-ESI m/z :562.1[M+H] ⁺ .

Example 6

Synthesis of N-p-toluoyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6f)

The experimental procedure is the same as in Example 1, only p-tolyl is used instead of methyl. The detection data of the product obtained from the reaction are as follows: Yield: 61%; Melting point: 198-200°C; ¹ H NMR (400MHz, CDCl ₃ ) δ: 2.38(s, 3H, -CH ₃ ), 7.23(d, J=8.4Hz ,1H,Ar-H),7.29(d,J=8.0Hz,1H,Ar-H),7.43-7.49(m,7H,Ar-H),7.61(d,J=8.0Hz,1H,Ar- H),7.67(d,J=8.4Hz,1H,Ar-H),7.80-7.82(m,1H,Ar-H),8.44(br s,1H,-CONHSO ₂ -); MS-ESI m/ z:576.2[M+H] ⁺ .

Example 7

Synthesis of N-2,4-methoxyphenylformyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6g)

The experimental procedure is the same as in Example 1, except that methyl is replaced by 2,4-methoxyphenyl. The detection data of the product obtained from the reaction are as follows: Yield: 49%; Melting point: 218-220°C; ¹ H NMR (400MHz, CDCl ₃ ) δ: 1.20(s,3H,4'-OCH ₃ ), 1.22(s,3H, 2'-OCH ₃ ),7.22(d,J=8.4Hz,1H,Ar-H),7.28(d,J=8.0Hz,1H,Ar-H),7.41-7.48(m,5H,Ar-H ),7.59(d,J=8.4Hz,2H,Ar-H),7.66(d,J=8.8Hz,1H,Ar-H),7.81(d,J=7.2Hz,1H,Ar-H), 9.07(br s,1H,-CONHSO2-); MS-ESI m/z:622.5[M+H] ⁺ .

Example 8

Synthesis of N-2,4-fluorophenylformyl-[(4-chlorophenyl)(4-trifluoromethylsulfonylphenyl)-one]semicarbazone (6h)

The experimental procedure is the same as in Example 1, except that methyl is replaced by 2,4-fluorophenyl. The detection data of the product obtained from _the reaction are as follows: The detection data of the product obtained from the reaction are as follows: Yield: 43% ^; -H),7.30-7.48(m,6H,Ar-H),7.60(d,J=8.0Hz,2H,Ar-H),7.65(d,J=8.4Hz,1H,Ar-H),7.95 (m,1H,Ar-H),8.27(s,1H,-CONHSO2-);MS-ESI m/z:599.8[M+H] ⁺ .

Embodiment 9: The compound (6a-h) biological activity test of embodiment 1-8

1) Test insects: Test insects: 1) Tetranychus cinnabarinus: female adult mites of Tetranychus cinnabarinus, collected from soybean seedlings in the field of Gansu Academy of Agricultural Sciences;

2) Bean aphid: adult bean aphid, collected from bean seedlings in the field of Gansu Academy of Agricultural Sciences, is a sensitive strain that has not been exposed to any pesticides. the

2) Drugs to be tested: the drugs are compounds 6a-h (prepared according to Example 1). the

3) Activity assay:

1) Determination of the poisonous activity of Tetranychus cinnabarinus: refer to the standard method for the determination of pest mites recommended by FAO (Food and Agriculture Organization of the United Nations)-slide dipping method and improve it (Wang Y.J., et al.Agrochemical Research Application.2006,10,20– twenty three.). Cut the double-sided tape into 2-3 cm long, stick it on one end of the microscope slide, use tweezers to peel off the paper on the tape, use a zero brush to select the female adult mites with the same size, bright body color and lively action, and place them on the Its back is glued on the double-sided adhesive tape (note: do not stick to mite feet, mite whiskers and mouthparts), stick 3 rows on each sheet, and stick 10 heads on each row. Place them in a biochemical incubator at a temperature of (25±1)°C and a relative humidity of about 85% for 4 hours, observe with binoculars, and remove dead or inactive individuals. Based on the pre-test, the target compound was diluted with water into 5 solutions with different concentrations. Immerse the end of the glass slide with mite in the solution, shake it gently for 5 seconds, take it out, and quickly absorb the excess liquid around the mite body and its surroundings with absorbent paper. . Put it in the above-mentioned biochemical incubator, and check the result with binocular mirror after 24 hours. Lightly touch the mites with a brush, and those who do not move their feet are considered dead. Soaked water was used as a control. The mortality rate of the control group was less than 10% as an effective test, and the mortality rate of the treatment group was corrected by Abbott's formula. Mortality of compounds was calculated at 500 ppm and 250 ppm. the

3) Determination of bean aphid poisonous activity: refer to the reported authoritative classic test method - spot method (Zhao Q.Q., Li Y.Q., Xiong L.X., et al. J. Agric. Food Chem. 2010, 58, 4992? 4998.). Dissolve the compound in an appropriate amount of acetone to make a concentration of 1 g/L, and then dilute it with an aqueous solution containing Tween 20 to different concentrations. Three replicates were set up for each concentration, and each replicate was a petri dish. The back of the bean aphid was dripped with a micro-dropper, and the drip volume per insect was 0.03 μL. After dripping, each treatment was placed in a biochemical incubator with a temperature of 24-25°C and a relative humidity of about 85%, and the mortality was detected after 24 hours. The control group was tested with acetone alone. The mortality rate of the control group was less than 10% as an effective test, and the mortality rate of the treatment group was corrected by Abbott's formula. Mortality of compounds was calculated at 500 ppm and 250 ppm. the

The test results are shown in Table 1.

Table 1 Example Benzophenone Hydrazone Sulfonylurea Compounds 6a-h Toxic activity against Tetranychus cinnabarinus and Bean Aphid

As can be seen from the bioassay results in Table 1, at a concentration of 500ppm, all compounds have more than 80% poisonous activity against bean aphid adults and Tetranychus cinnabarinus adult mites, especially 100% for Tetranychus cinnabarinus; at a concentration of 250ppm , except for compound 6f and compound 6h which inhibited 26.67% and 36.67% of bean aphid adults respectively, all the other compounds showed good activity, and except for compound 6b which inhibited 40% of adults All the compounds showed high poisonous activity against adults of Tetranychus cinnabarinus. the

In summary, the benzophenone derivatives described in the present invention have a novel structure and are easy to synthesize. The biological test results show that most of the compounds show significant insecticidal and acaricidal activities, which have further research value and are expected to be developed into new Agricultural insecticides and acaricides. the

Claims (8)

1. a benzophenone hydrazone sulfonyl urea compound, it is characterized in that its chemical general formula for ( i) compounds shown in formula:

（ I）

Wherein in (I) formula R be methyl, 2-naphthyl, phenyl, to fluorophenyl, rubigan, p-methylphenyl, 2,4-p-methoxy-phenyls or 2,4-fluorophenyl.

2. the preparation method of compound according to claim 1, is characterized in that under nitrogen protection, and temperature of reaction is the reflux temperature of room temperature to selected solvent, and adopts general formula in a solvent iIshown reaction equation is carried out reaction 2 ~ 10 hours and obtains, and reaction equation is such as formula shown in II

formula II.

3. the preparation method of compound according to claim 2, is characterized in that the solvent selected by reacting is benzene, toluene, tetrahydrofuran (THF), dimethyl sulfoxide (DMSO), acetone, methylene dichloride , N, N-dimethyl formamide; These solvents are used alone or used in combination, and the ratio of mixed solvent can be: 1 ~ 5:100.

4. the best preparation method of compound according to claim 2, 1 ~ 1.5mmol sulfonamido ethyl formate is it is characterized in that to be dissolved in 10mL toluene, sulfonamido ethyl formate used is the amino ethyl formate of sulfonyloxy methyl, 2-naphthalene sulfonyl urethanum, phenylsulfonyl-amido ethyl formate, to fluorophenyl sulfonamido ethyl formate, p-methylphenyl sulfonamido ethyl formate, 2, 4-methoxyphenyl sulphonyl urethanum or 2, any one in 4-fluorophenyl sulfonamido ethyl formate, be heated to boil, under nitrogen protection, after 2 ~ 3mmol benzophenone hydrazone parent is dissolved in 10mL toluene, be added drop-wise in reaction solution, reflux 2 ~ 4 hours, after completion of the reaction, after removing solvent under reduced pressure, crude by column chromatography purifying, carry out column chromatography (eluent system is sherwood oil: acetone), obtain target compound benzophenone hydrazone sulfonyl urea compound.

5. method according to claim 2, is characterized in that silica gel for chromatography post adopts 200 ~ 300 object column chromatography silica gel.

6. method according to claim 2, its feature is at eluent petroleum ether used: the volume ratio of acetone is: 10:1 ~ 20:1.

7. the compound of formula I according to claim 1 is used for the purposes of pest control.

8. purposes according to claim 7, is characterized in that described Agricultural pests are carmine spider mite and bean aphid.