A benzoylurea derivative and its preparation method and application

Abstract

The present invention relates to the technical field of agricultural chemicals and their preparation. Specifically, it discloses a benzoylurea derivative, its preparation method, and its application. Its structure is shown in Formula (I). The structure retains the benzoyl moiety and introduces a substituted phenylpyridine functional group, making it easier to form hydrogen bonds in vivo, thereby improving donor-acceptor affinity and effectively enhancing the compound's insecticidal activity. The compound exhibits excellent insecticidal activity even at relatively low concentrations, particularly against Lepidoptera larvae. It is a novel and highly effective biopesticide that can alleviate the resistance of pests and diseases to traditional drugs. It is non-toxic to mammals and aquatic organisms, poses minimal environmental pollution, and possesses high pesticide research value, with broad application prospects in agriculture. #imgabs0#

Description

Technical Field

[0001] The present invention relates to the field of agricultural chemicals and preparation technology, in particular to a benzoyl urea derivative and a preparation method and application thereof. Background Art

[0002] Pests and diseases are one of the major limiting factors in agricultural production. Many pests and diseases not only directly harm agricultural products but also spread diseases, thereby reducing the yield and quality of agricultural products. Many agricultural systems rely heavily on certain traditional insecticides for pest control. However, these traditional insecticides have drawbacks such as high toxicity, high residual effects, and low activity. Long-term use of traditional insecticides can lead to significant resistance in pests. Therefore, there is a need to develop new insecticides that are highly effective, low in toxicity, and low in residual effects.

[0003] Benzoylurea compounds are insect chitin inhibitors that are easily hydrolyzed in soil and water and have the advantages of broad spectrum, high efficiency, low toxicity, low residue, and ease of use. Furthermore, thanks to their unique mechanism of action, they can inhibit the synthesis of chitin, a substance present in insects but not in mammals, hindering insect metamorphosis and leading to insect death or sterility. They have been widely used in the control of crop pests and diseases, and many commercial pesticides, such as lufenuron, diflubenzuron, and flubendiamide, are currently available. However, currently available benzoylurea products are not highly effective in killing pests, and some also have toxic side effects on aquatic organisms. Alternatively, some products have high production costs, making them unsuitable for large-scale production and application. Therefore, designing and synthesizing a new type of benzoylurea compound to reduce the resistance of pests and diseases to pesticides and to provide more highly effective insecticidal compounds for the pesticide field is of great significance. Summary of the Invention

[0004] In order to solve the above problems, the present invention provides a benzoylurea derivative and a preparation method and application thereof.

[0005] In order to solve the above technical problems, the technical solution provided by the present invention is:

[0006] A benzoyl urea derivative, the structure of which is shown in formula (I):

[0007]

[0008] Wherein, X1 and X2 are F, Cl or Br; R is a linear or branched halogenated or unsubstituted C1-C5 alkyl group, a linear or branched C1-C5 alkoxy group, a sulfonyl group, a nitro group or a carboxyl group.

[0009] The present invention designs and synthesizes a novel benzoyl urea derivative, the structure of which retains the benzoyl moiety and introduces a substituted phenylpyridine functional group. The derivative is more likely to form hydrogen bonds in organisms, thereby improving the donor-acceptor affinity and effectively enhancing the insecticidal activity of the compound. The derivative also has excellent insecticidal activity at lower agent concentrations, especially high insecticidal activity against Lepidoptera larvae. The derivative is a novel and highly effective biopesticide that can alleviate the resistance of pests and diseases to traditional drugs, is non-toxic to mammals and aquatic organisms, and has little environmental pollution. The derivative has high pesticide research value and has broad application prospects in agriculture.

[0010] Preferably, X1 and X2 are F or Cl; and R is a linear or branched halogenated or unsubstituted C1-C5 alkyl group, or a linear or branched C1-C5 alkoxy group.

[0011] Preferably, the structural formula of the benzoyl urea derivative is:

[0012]

[0013] The preferred compound has excellent insecticidal activity against Lepidoptera larvae, can significantly reduce the amount of pesticide used, and can achieve a 100% lethality rate against Lepidoptera larvae at a concentration of 20 mg / L. It can effectively reduce the cost of pest control and reduce the pollution of pesticides to the environment, and has high practical value.

[0014] The present invention also provides a method for preparing a benzoyl urea derivative, comprising the following steps:

[0015] Step a: In solvent A, a substituted phenylhydrazine represented by formula (II) and ethoxymethylenemalononitrile are subjected to a Huisgen reaction to obtain a compound represented by formula (III);

[0016]

[0017] Step b: in solvent B, reacting the compound represented by formula (III) with the substituted benzoyl isocyanate represented by formula (IV) to obtain the benzoyl urea derivative represented by formula (I);

[0018]

[0019] The specific reaction route is as follows:

[0020]

[0021] The preparation method of the benzoyl urea derivative provided by the present invention is simple, the raw materials are readily available, no special equipment is required, the production efficiency is high, and the method is suitable for industrial production.

[0022] Preferably, in step a, the solvent A is at least one of water, methanol, ethanol, isopropanol, acetone, n-butanol, tetrahydrofuran, methyl formate, chloroform, dichloromethane, ethyl ether, isopropyl ether, methyl tert-butyl ether, benzene, toluene, xylene, carbon tetrachloride, n-hexane, cyclohexane, ethylenediamine or ethanolamine.

[0023] Further preferably, in step a, the solvent A is at least one of water, methanol, ethanol, isopropanol or n-butanol.

[0024] Preferably, in step a, the molar ratio of the substituted phenylhydrazine to the ethoxymethylenemalononitrile is 1:1-1:2.

[0025] Preferably, in step a, the volume molar ratio of the solvent A to the substituted phenylhydrazine is 50-100:0.2-0.4, wherein the unit of volume is milliliter.

[0026] Preferably, in step a, the temperature of the Huisgen reaction is 60° C.-100° C., and the reaction time is 2 h-6 h.

[0027] Preferably, in step a, after the reaction is completed, a purification step is further included: evaporating the reaction solution to dryness, washing, and drying, adding the resulting crude product to chloroform, heating to dissolve, cooling to crystallize, separating, and drying to obtain the compound represented by formula (III).

[0028] In combination with the above, in step a, the temperature for heating and dissolving is 50°C-70°C, and the heating time is 5min-15min.

[0029] In combination with the above, in step a, the volume-to-mass ratio of chloroform to the crude product is 1:8-12, wherein the unit of volume is milliliter and the unit of mass is milligram.

[0030] In combination with the above, in step a, the temperature for cooling and crystallization is room temperature, and the crystallization time is 40 min-60 min.

[0031] Preferably, in step b, the solvent B is N,N-dimethylformamide, dimethyl sulfoxide, ethyl acetate, 1,4-dioxane, benzene, toluene, xylene, acetonitrile, malononitrile, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, tetrahydrofuran, chlorobenzene, ether, methyl ethyl ketone, methyl isopropyl ketone or methyl isobutyl ketone.

[0032] Further preferably, in step b, the solvent B is at least one of N,N-dimethylformamide, dimethyl sulfoxide, ethyl acetate, toluene, dichloromethane, chloroform or 1,2-dichloroethane.

[0033] Preferably, in step b, the molar ratio of the compound represented by formula (III) to the substituted benzoyl isocyanate is 1:2-1:5.

[0034] Preferably, in step b, the volume molar ratio of the solvent B to the compound represented by formula (III) is 60-120:0.1-0.3, wherein the unit of volume is milliliter.

[0035] Preferably, in step b, the temperature of the addition reaction is 70° C.-100° C., and the reaction time is 1 h-4 h.

[0036] Preferably, in step b, after the reaction is completed, a purification step is further included: evaporating the reaction solution to dryness, washing, and drying, adding the obtained crude product to anhydrous ethanol, heating to dissolve, cooling to crystallize, separating, and drying to obtain the compound represented by formula (III).

[0037] In combination with the above, in step b, the temperature for heating and dissolving is 70°C-80°C, and the heating time is 5min-15min.

[0038] In combination with the above, in step b, the volume-to-mass ratio of anhydrous ethanol to the crude product is 1:8-12, wherein the unit of volume is milliliter and the unit of mass is milligram.

[0039] In combination with the above, in step b, the temperature for cooling and crystallization is room temperature, and the crystallization time is 20 min-30 min.

[0040] The present invention also provides the use of the benzoyl urea derivatives in preventing and controlling plant diseases and insect pests.

[0041] The benzoylurea derivatives provided by the present invention can be used for preventing and controlling various agricultural pests, such as Lepidoptera, Hemiptera, Coleoptera, Diptera, Orthoptera and Homoptera pests, and have high prevention and control effects.

[0042] Preferably, the benzoyl urea derivatives of formula (I) are particularly suitable for the control of Lepidoptera larvae.

[0043] The benzoylurea derivatives described in formula (I) can be used to prevent and control various agricultural pests and diseases, and have a high control effect on Lepidoptera larvae.

[0044] The present invention also provides a pharmaceutical composition for preventing and treating lepidopteran larvae, comprising the benzoyl urea derivative described in formula (I).

[0045] When used as a pharmaceutical active ingredient for controlling crop pests and diseases, various methods or techniques can be used. For example, the benzoylurea derivative described in formula (I) can be combined with conventional adjuvants in the pesticide field to form various dosage forms, such as suspension concentrates, emulsifiable concentrates, granules, or powders. Conventional pesticide application methods, such as dipping or spraying, can be used to control plant roots, stems, or leaves. The agent has a high control effect on Lepidoptera larvae at a concentration of 10 mg / L to 20 mg / L and is non-toxic to mammals and aquatic organisms. It is a new, green and environmentally friendly pesticide with high industrialization potential and social and environmental benefits. DETAILED DESCRIPTION

[0046] In order to make the purpose, technical solutions and advantages of the present invention more clearly understood, the present invention is further described in detail below in conjunction with the embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention.

[0047] Example 1

[0048] This example provides a method for preparing N-2,6-difluorobenzoyl-N'-[(1-(4-trifluoromethylphenyl)-4-cyanopyrazolyl]urea (Ia):

[0049] Step 1. Dissolve 55.01 g (0.312 mol) of 4-trifluoromethylphenylhydrazine and 38.14 g (0.312 mol) of ethoxymethylenemalononitrile in 90 mL of anhydrous ethanol, heat to 70 ° C, stir and react for 4 hours, cool to room temperature, evaporate the solvent, wash, and dry. Add the resulting crude product to chloroform solvent (the ratio of crude product to chloroform is 10 mg: 1 mL), heat at 55 ° C for 10 min to dissolve the crude product, cool to room temperature, crystallize for 50 min, filter, and dry to obtain a yellow solid 1- (4-trifluoromethylphenyl) -4-cyano-5-aminopyrazole.

[0050] Step 2. Dissolve 68.34 g (0.271 mol) of 1-(4-trifluoromethylphenyl)-4-cyano-5-aminopyrazole and 198.49 g (1.084 mol) of 2,6-difluorobenzoyl isocyanate in 100 mL of 1,2-dichloroethane, heat to 80 ° C, stir and react for 3 h, cool to room temperature, evaporate the solvent, wash, and dry. Add the resulting crude product to anhydrous ethanol solvent (the ratio of crude product to anhydrous ethanol is 10 mg: 1 mL), heat at 75 ° C for 10 min to dissolve the crude product, cool to room temperature, crystallize for 30 min, filter, and dry to obtain white solid N-2,6-difluorobenzoyl-N'-[(1-(4-trifluoromethylphenyl)-4-cyanopyrazolyl] urea (Ia) with a yield of 84% and a purity of 95%.

[0051]

[0052] 1 H NMR (500Hz, DMSO-d6) δ11.80(s,1H),10.49(s,1H),8.42(s,1H),8.11(m,2H),7.87(d,2H),7.66(m,1H),7.28(t,2H).

[0053] 13 C NMR (125MHz, DMSO-d6) δ163.97,162.57,162.20,161.97,161.30,159.26,158.79,155.25,149.50, 142.63,138.34,134.59,132.78,126.92,126.85,117.08,116.90,112.84,112.63,112.20,89.19.

[0054] The compound represented by formula (Ia) can be prepared by using other reaction conditions and reaction solvents specified in the specification of the present invention, and the technical effects basically equivalent to the above can be achieved.

[0055] Example 2

[0056] Preparation of N-2,6-difluorobenzoyl-N'-[(1-(4-isopropylphenyl)-4-cyanopyrazolyl]urea (Ib):

[0057] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-isopropylphenylhydrazine. The other conditions were the same as those in Example 1 to synthesize N-2,6-difluorobenzoyl-N'-[(1-(4-isopropylphenyl)-4-cyanopyrazolyl]urea (Ib). It was a white solid with a yield of 78% and a purity of 90%.

[0058]

[0059] 1 H NMR(500Hz,DMSO-d6)δ11.81(s,1H),10.44(s,1H),8.37(s,1H),7.88(t,1H),7.75(m ,1H),7.67(m,1H),7.65(m,1H),7.56(t,1H),7.28(t,2H),3.30(q,1H),1.55(d,6H).

[0060] 13C NMR(125MHz,DMSO-d6)δ162.47,161.98,160.10,160.43,158.11,150.40,143.24,141.00,138.85,134.12, 133.52,132.43,131.94,130.52,127.26,123.75,122.33,120.52,113.13,112.86,112.80,112.63,91.10.

[0061] Example 3

[0062] Preparation of N-2,6-difluorobenzoyl-N'-[(1-(3-nitrophenyl)-4-cyanopyrazolyl]urea (Ic):

[0063] Following the method of Example 1, except that 4-trifluoromethylphenylhydrazine in step 1 was replaced with 3-nitrophenylhydrazine, and the reaction solvent in step 2 was replaced with toluene, and the remaining conditions were the same as in Example 1, N-2,6-difluorobenzoyl-N'-[(1-(3-nitrophenyl)-4-cyanopyrazolyl]urea (Ic) was synthesized as a white solid with a yield of 75% and a purity of 94%.

[0064]

[0065] 1 H NMR (500Hz, DMSO-d6) δ11.83(s,1H),10.50(s,1H),8.50(s,1H),8.21(m,2H),7.96(m,1H),7.66(m,1H),7.28(t,1H),7.12(td,2H).

[0066] 13 C NMR(125MHz,DMSO-d6)δ164.55,162.71,160.25,155.86,153.86,153.45,144.76,138.62,137 .65,132.66,125.72,128.61,128.55,126.37,127.71,114.22,117.46,111.52,111.34,41.38.

[0067] Example 4

[0068] Preparation of N-2,6-difluorobenzoyl-N'-[(1-(3-ethoxyphenyl)-4-cyanopyrazolyl]urea (Id):

[0069] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 3-ethoxyphenylhydrazine, and the reaction solvent in step 1 was replaced by n-butanol, and the reaction solvent in step 2 was replaced by toluene. The other conditions were the same as those in Example 1, and N-2,6-difluorobenzoyl-N'-[(1-(3-ethoxyphenyl)-4-cyanopyrazolyl]urea (Id) was synthesized. It was a white solid with a yield of 64% and a purity of 93%.

[0070]

[0071] 1 H NMR(500MHz,DMSO-d6)δ11.81(s,1H),10.44(s,1H),8.37(s,1H),7.88(t,1H),7 .75(ddd,1H),7.65(m,2H),7.56(t,1H),7.28(t,2H),4.14(q,2H),1.46(d,3H).

[0072] 13 C NMR (125MHz, DMSO-d6) δ162.45,161.26,160.15,159.62,158.10,156.79,155.79,150.37,143.21,140 .97,138.82,134.10,132.41,131.93,127.25,123.73,122.31,113.09,113.42,112.82,112.64,91.08.

[0073] Example 5

[0074] Preparation of N-2,6-difluorobenzoyl-N'-[(1-(4-methylphenyl)-4-cyanopyrazolyl]urea (Ie):

[0075] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-methylphenylhydrazine, and the reaction solvent in step 2 was replaced by ethyl acetate. The other conditions were the same as those in Example 1 to synthesize N-2,6-difluorobenzoyl-N'-[(1-(4-methylphenyl)-4-cyanopyrazolyl]urea (Ie). It was obtained as a white solid with a yield of 84% and a purity of 91%.

[0076]

[0077] 1H NMR (500MHz, DMSO-d6) δ11.75(s,1H),10.37(s,1H),8.31(s,1H),7.65(tt,1H),7.51(d,2H),7.39(d,2H),7.27(t,2H),2.40(s,3H).

[0078] 13 C NMR(125MHz,DMSO-d6)δ162.45,160.15,158.16,150.36,142.69,140.51,139.34,135.22 ,134.06,130.33,124.63,121.90,113.64,113.47,113.36,112.81,112.61,90.37,21.16.

[0079] Example 6

[0080] Preparation of N-2,6-difluorobenzoyl-N'-[(1-(4-methoxyphenyl)-4-cyanopyrazolyl]urea (If):

[0081] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-methoxyphenylhydrazine. The other conditions were the same as those in Example 1 to synthesize N-2,6-difluorobenzoyl-N'-[(1-(4-methoxyphenyl)-4-cyanopyrazolyl]urea (If). It was a white solid with a yield of 70% and a purity of 97%.

[0082]

[0083] 1 H NMR (500MHz, DMSO-d6) δ11.85(s,1H),10.43(s,1H),8.23(s,1H),7.66(tt,1H),7.50(d,2H),7.44(d,2H),7.31(t,2H),4.40(s,3H).

[0084] 13 C NMR(125MHz,DMSO-d6)δ161.04,160.98,160.36,160.30,159.75,158.35,151.75,143.63, 142.15,132.84,132.70,132.58,123.38,114.94,113.46,113.30,113.13,112.08,76.51.

[0085] Example 7

[0086] Preparation of N-2,6-dichlorobenzoyl-N'-[(1-(4-methylphenyl)-4-cyanopyrazolyl]urea (1 g):

[0087] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-methylphenylhydrazine, and 2,6-difluorobenzoyl isocyanate in step 2 was replaced by 2,6-dichlorobenzoyl isocyanate. The other conditions were the same as those in Example 1 to synthesize N-2,6-dichlorobenzoyl-N'-[(1-(4-methylphenyl)-4-cyanopyrazolyl]urea (1 g). White solid, yield 84%, purity 96%.

[0088]

[0089] 1 H NMR(500MHz,DMSO-d6)δ11.70(s,1H),10.35(s,1H),8.30(s,1H),7.68(d,1H ),7.61(tt,6.6Hz,1H),7.53(d,1H),7.48(d,2H),7.23(t,2H),2.37(s,3H).

[0090] 13 C NMR(125MHz,DMSO-d6)δ162.47,160.15,160.10,158.16,158.10,150.37,143.05,140.82 ,137.17,136.47,134.14,132.37,124.75,123.29,113.44,113.16,112.82,90.88,20.31.

[0091] Example 8

[0092] Preparation of N-2,6-dibromobenzoyl-N'-[(1-(4-tert-butylphenyl)-4-cyanopyrazolyl]urea (Ih):

[0093] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-tert-butylphenylhydrazine, 2,6-difluorobenzoyl isocyanate in step 2 was replaced by 2,6-dibromobenzoyl isocyanate, and the reaction solvent in step 2 was replaced by toluene. The other conditions were the same as those in Example 1 to synthesize N-2,6-dibromobenzoyl-N'-[(1-(4-tert-butylphenyl)-4-cyanopyrazolyl]urea (Ih). White solid, yield 78%, purity 90%.

[0094]

[0095] 1H NMR (500MHz, DMSO-d6) δ11.78(s,1H),10.41(s,1H),8.36(s,1H),7.68(d,2H),7.55(tt,1H),7.42(d,2H),7.26(t,2H),1.34(s,9H).

[0096] 13 C NMR(125MHz,DMSO-d6)δ160.88,160.26,158.45,158.24,150.82,146.93,146.32,144.12,137.72,13 2.38,132.02,123.72,121.82,116.34,114.32,112.73,112.17,112.08,111.06,76.11,38.12,33.71.

[0097] Example 9

[0098] Preparation of N-2,6-dichlorobenzoyl-N'-[(1-(4-methylsulfonylphenyl)-4-cyanopyrazolyl]urea (Ii):

[0099] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-methylsulfonylphenylhydrazine hydrochloride, 2,6-difluorobenzoyl isocyanate in step 2 was replaced by 2,6-dichlorobenzoyl isocyanate, and the reaction solvent in step 2 was replaced by N,N-dimethylformamide. The other conditions were the same as those in Example 1 to synthesize N-2,6-dichlorobenzoyl-N'-[(1-(4-methylsulfonylphenyl)-4-cyanopyrazolyl]urea (Ii). It was a white solid with a yield of 70% and a purity of 98%.

[0100]

[0101] 1 H NMR (500MHz, DMSO-d6) δ11.73(s,1H),10.26(s,1H),8.56(s,1H),8.08(d,1H),7.56(m,2H),7.24(t,2H).

[0102] 13 C NMR (126MHz, DMSO-d6) δ162.69,161.96,160.26,159.03,158.01,150.51,146.15,141 .65,136.44,134.21,134.72,134.82,131.13,130.68,129.14,113.84,112.81,88.55.

[0103] Example 10

[0104] Preparation of N-2,6-dichlorobenzoyl-N'-[(1-(4-carboxyphenyl)-4-cyanopyrazolyl]urea (Ij):

[0105] According to the method of Example 1, 4-trifluoromethylphenylhydrazine in step 1 was replaced by 4-carboxylphenylhydrazine, and 2,6-difluorobenzoyl isocyanate in step 2 was replaced by 2,6-dichlorobenzoyl isocyanate. The other conditions were the same as those in Example 1 to synthesize N-2,6-dichlorobenzoyl-N'-[(1-(4-carboxyphenyl)-4-cyanopyrazolyl]urea (Ij). White solid, yield 68%, purity 80%.

[0106]

[0107] 1 H NMR (500Hz, DMSO-d6) δ11.82(s,1H),10.50(s,1H),8.43(s,1H),8.14(m,2H),7.90(d,2H),7.69(m,1H),7.30(t,2H).

[0108] 13 C NMR(125MHz,DMSO-d6)δ168.62,164.64,160.16,159.30,158.24,156.32,156.79,151.64, 143.64,141.85,141.17,132.56,130.83,127.36,120.82,113.14,112.46,112.22,76.61.

[0109] Efficacy trials

[0110] The toxicity of the compounds of formula (I) prepared in Examples 1-10 of the present invention and hexaflumuron to armyworms and corn borers was tested indoors to compare and evaluate the insecticidal activities.

[0111] Test method: leaf immersion method.

[0112] 2.1 Preparation of medicine

[0113] The test agent was prepared using N,N-dimethylformamide as solvent and water as diluent to prepare different concentrations of the agent. The N,N-dimethylformamide content in the agent was 0.1 wt%, and the agent concentrations were 20 mg / L, 15 mg / L, and 10 mg / L.

[0114] 2.3 Experimental process

[0115] Leaves approximately 5-6 cm in diameter were immersed in the solution, dried, and placed in designated petri dishes. Ten third-instar armyworm or corn borer larvae of consistent size and physiological state were inoculated. A control group was reared with leaves soaked in the solution. The petri dishes were sealed and placed in a constant temperature incubator at 25°C. After 72 hours, the number of deaths was examined and recorded. Four replicates were set up in parallel, and mortality was calculated. The results are shown in Tables 1 and 2.

[0116] Table 1 Mortality of armyworms at different concentrations of the tested pesticides

[0117]

[0118]

[0119] Table 2 The mortality rate of corn borer under different concentrations of the tested pesticides

[0120]

[0121] As can be seen from the above table, among the test samples, only compound Ia, compound Ib, compound Id, compound Ie, compound If and compound Ig have high insecticidal activity against armyworm and corn borer. Among them, the lethality of compound Ia against armyworm at the three test doses in the initial screening was 100%, 100% and 97.5%, respectively, and the lethality of compound Ia against corn borer at the three test doses in the initial screening was 100%, 97.5% and 90%, respectively. It still has high insecticidal activity at a low agent concentration (10 mg / L).

[0122] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions or improvements made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A use of a benzoylurea derivative in controlling lepidopteran larvae, characterized in that: Its structure is shown in formula (I): Formula (I); Wherein, X1 and X2 are F or Cl; R is a linear or branched C1-C5 alkoxy group, a linear or branched halogenated or unsubstituted C1-C5 alkyl group.

2. The use of the benzoylurea derivative in controlling Lepidoptera larvae according to claim 1, characterized in that: Its structural formula is: 。 3. Use of the benzoylurea derivative according to claim 1 or 2 in controlling lepidopteran larvae, characterized in that: The benzoyl urea derivative is prepared according to the following steps: Step a: reacting a substituted phenylhydrazine represented by formula (II) with ethoxymethylenemalononitrile in solvent A to obtain a compound represented by formula (III); Step b: in solvent B, reacting the compound represented by formula (III) with the substituted benzoyl isocyanate represented by formula (IV) to obtain the benzoyl urea derivative represented by formula (I); 。 4. The use of the benzoylurea derivative in controlling Lepidoptera larvae according to claim 3, characterized in that: In step a, the solvent A is at least one of methanol, ethanol, isopropanol or n-butanol; In step b, the solvent B is ethyl acetate, benzene, toluene, xylene, chloroform, carbon tetrachloride or 1,2-dichloroethane.

5. The use of the benzoylurea derivative in controlling lepidopteran larvae according to claim 4, characterized in that: In step a, the molar ratio of the substituted phenylhydrazine to the ethoxymethylenemalononitrile is 1:1-1:2; In step a, the volume molar ratio of the solvent A to the substituted phenylhydrazine is 50-100:0.2-0.4, wherein the unit of volume is milliliter; In step a, the reaction temperature is 60° C.-100° C., and the reaction time is 2 h-6 h.

6. Use of the benzoylurea derivative in controlling Lepidoptera larvae according to claim 3, characterized in that: In step b, the molar ratio of the compound represented by formula (III) to the substituted benzoyl isocyanate is 1:2-1:5; In step b, the volume molar ratio of the solvent B to the compound represented by formula (III) is 60-120:0.1-0.3, wherein the unit of volume is milliliter; In step b, the temperature of the addition reaction is 70° C.-100° C., and the reaction time is 1 h-4 h.

Images