An imidazo[4,5-g]quinoline-2-one compound and its use as an insecticide

Abstract

The present invention belongs to the field of pesticides, and relates to an imidazo[4,5-g]quinoline-2-one compound and its application as a pesticide. The structural formula of the imidazo[4,5-g]quinoline-2-one compound is shown in Formula I:, and the results of biological activity assays show that the compound prepared by the present invention has excellent insecticidal activity, and it is found that the compound obtained by the present invention can be more effectively compounded with diprofenopyrin and sulfoxaflor to delay the drug resistance of pests, and has fast-acting property, long-lasting effect and storage stability, and can be present in water-dispersible granules, suspensions, microemulsions, aqueous emulsions, emulsifiable concentrates and wettable powders.

Description

Technical Field

[0001] The invention belongs to the field of pesticides and relates to an imidazo[4,5-g]quinoline-2-one compound and an application thereof as a pesticide. Background Art

[0002] Sulfoxaflor is a sulfoximine insecticide suitable for the control of all piercing-sucking mouthparts pests such as cotton blind bugs, aphids, whiteflies, planthoppers and scales. Because of its high efficiency, rapidity and long-lasting effect, it can effectively control sap-sucking pests that are resistant to nicotine, pyrethroid, organophosphate and carbamate pesticides; it has low toxicity to non-target arthropods and is the preferred agent for integrated pest control, but it is not recommended to be used alone.

[0003] Abiprofen is a new insecticide for controlling piercing-sucking mouthparts pests, with the characteristics of fast onset, high efficiency and broad spectrum. Abiprofen interferes with the function of insects' chord organs, causing insects to lose their sense of gravity, balance, sound, position and movement, making them deaf, lose coordination and sense of direction, and thus unable to feed, lose water, and eventually die of starvation. Abiprofen can effectively reduce viral and bacterial diseases transmitted by insect vectors and has excellent insecticidal effects. It also has the advantages of long lasting effect and strong leaf penetration ability.

[0004] However, insecticides with a single active ingredient have the disadvantages of poor control effect, easy occurrence of drug resistance after continuous use, high frequency and dosage of drug use, and high cost in actual application. Although studies have found and proved that the combined use of flubendiamide and cypermethrin can preferentially delay the development of drug resistance in cotton aphids and has a synergistic insecticidal effect. However, in current practical applications, it is still of great significance to invent new compounds with insecticidal activity, improve existing compounds and compositions, and design pollution-free biological pesticides with good prevention effects on piercing-sucking and sucking insects. Summary of the invention

[0005] In view of the above problems, the purpose of the present invention is to provide an imidazo[4,5-g]quinoline-2-one compound and its preparation method and application. Such compounds have excellent insecticidal activity and can be used as insecticides for the prevention and treatment of agricultural diseases. At the same time, the compound obtained by the present invention can be compounded with sulfoxaflor and sulfoxaflor, which can more effectively delay the drug resistance of pests and has the characteristics of rapid effect, long-lasting effect and storage stability. To achieve the above purpose, the present invention adopts the following technical scheme.

[0006] An imidazo[4,5-g]quinoline-2-one compound, the general structural formula (I) of which is as follows:

[0007] , wherein R is selected from H, OCF3, or CF3.

[0008] Another object of the present invention is to provide a synthetic route of an imidazo[4,5-g]quinoline-2-one compound of formula (I):

[0009] .

[0010] Furthermore, the synthesis method of each step in the above-mentioned synthesis route is as follows:

[0011] 1) Add ethanol to the reaction bottle, then add quinoline-6,7-diamine (Compound 1), stir to dissolve, then add potassium hydroxide, stir for 10 minutes, slowly drop 4-methyl-3-oxopentanoic acid ethyl ester (Compound 2) into the system, stir at room temperature for 2 hours after the addition is complete, and after the reaction is completed by TLC monitoring, concentrate the reaction solution, add the concentrated reaction solution into water, stir for half an hour after crystallization, filter, wash the filter cake with water, and air dry at 50°C for 2 hours to obtain a light yellow solid 1-(3-methyl-1-butene-2-yl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (Compound 3);

[0012] 2) Compound 3 was added to DMF, sodium hydroxide was added, stirred for half an hour, 1,2-dichloroethane was added dropwise, and after the addition was complete, the mixture was stirred at room temperature for 10 hours. After the reaction was completed under TLC monitoring, the reaction solution was concentrated to a quarter of the original volume at below 70°C in a vacuum, and the remaining system was poured into cold water, stirred for crystallization for 1 hour, filtered, and dried in a vacuum at 50°C to obtain an off-white solid 3-(2-chloroethyl)-1-(3-methyl-1-butene-2-yl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (Compound 4);

[0013] 3.1) Compound 4 was added to tetrahydrofuran, sodium hydroxide and tetrahydropyrrole were added, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed under TLC monitoring, the mixture was concentrated under vacuum below 70°C until no more liquid flowed out. The residue was separated by flash column chromatography to obtain an off-white solid 1-(3-methyl-1-butene-2-yl)-3-(2-(pyrrolidin-1-yl)ethyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (Compound 5);

[0014] 3.2) Compound 4 was added to tetrahydrofuran, sodium hydroxide and 3-trifluoromethyltetrahydropyrrole were added, and the mixture was stirred at room temperature. After the reaction was completed under TLC monitoring, the mixture was concentrated under vacuum below 70°C until no more liquid flowed out. The residue was separated by flash column chromatography to obtain an off-white solid 1-(3-methyl-1-butene-2-yl)-3-(2-(3-trifluoromethylpyrrolidin-1-yl)ethyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (Compound 6);

[0015] 3.3) Compound 4 was added to tetrahydrofuran, sodium hydroxide and 3-trifluoromethoxytetrahydropyrrole were added, and the mixture was stirred at room temperature. After the reaction was completed under TLC monitoring, the mixture was concentrated under vacuum below 70°C until no more liquid flowed out. The residue was separated by flash column chromatography to obtain an off-white solid 1-(3-methyl-1-butene-2-yl)-3-(2-(3-trifluoromethoxypyrrolidin-1-yl)ethyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (Compound 7).

[0016] Some compounds 1 H-NMR (400 MHz) and 13 C-NMR (125 MHz) is as follows:

[0017] Compound 3: 1 H-NMR (400 MHz, CDCl3) δ: 1.15(d, 6H), 2.38(m, 1H), 4.35(d,2H), 6.49(d, 1H), 7.11(m, 1H), 7.90(m, 1H), 7.99(s, 1H), 8.52(m, 1H), 9.10(s,1H). 13 C-NMR (125 MHz, CDCl3) δ:21.06, 30.91, 98.04, 104.15, 107.99, 120.86, 129.93, 130.30, 135.39, 135.89, 140.28, 145.54, 149.59, 153.37.

[0018] Compound 4: 1 H-NMR (400 MHz, CDCl3) δ: 1.16(d, 6H), 2.37(m, 1H), 3.21(t,2H), 3.67(t, 2H), 4.35(d, 2H), 6.48(s, 1H), 7.10(m, 1H), 7.90(m, 1H), 7.99(s,1H), 8.52(m, 1H). 13 C-NMR (125 MHz, CDCl3) δ:21.06,30.91,42.21,42.66,95.64,99.93,107.96,120.90,130.06,133.51,135.30,140.56,144.22 ,149.56 ,156.19.

[0019] Compound 5:1 H-NMR (400 MHz, CDCl3) δ: 1.16(d, 6H), 1.82(m, 4H), 2.37(m,1H), 2.60(m, 4H), 3.20(t, 2H), 3.41(t, 2H), 4.36(s, 2H), 6.49(d, 1H), 7.10(m,1H), 7.89(m, 1H), 7.99(s, 1H), 8.54(m, 1H). 13 C-NMR (125 MHz, CDCl3) δ: 21.06, 23.70, 30.91, 40.21, 54.03, 56.51, 95.64, 99.93, 107.96, 120.90, 130.06, 133.51, 135.30, 140.56, 144.22, 149.56, 156.19.

[0020] Compound 6: 1 H-NMR (400 MHz, CDCl3) δ: 1.14(dd, 6H), 1.42(m, 1H), 1.65(m,1H), 2.27-2.44(m, 4H), 2.62(t, 2H), 2.87(m, 1H), 3.08(m, 1H), 3.41(t, 2H), 4.35(s, 2H), 6.49(s, 1H), 7.11(m, 1H), 7.90(d, 1H), 7.99(s, 1H), 8.54(m, 1H). 13 C-NMR (125 MHz, CDCl3) δ:21.06, 30.91, 33.48, 40.21, 45.38, 53.23, 56.86, 61.97, 95.64, 99.93, 107.96, 120.90, 130.06, 133.51, 135.30, 140.56, 144.08, 149.56, 156.19.

[0021] Compound 7: 1H-NMR (400 MHz, CDCl3) δ: 1.15(dd, 6H), 1.69(m, 1H), 2.19(m,2H), 2.39(m, 2H), 2.62(t, 3H), 2.99(m, 1H), 3.41(t, 2H), 3.88(m, 1H), 4.35(s,2H), 6.49(s, 1H), 7.11(m, 1H), 7.90(d, 1H), 7.99(s, 1H), 8.52(m, 1H). 13 C-NMR (125 MHz, CDCl3) δ: 21.06, 30.91, 35.59, 40.24, 50.52, 56.93, 60.94, 77.31, 95.64, 99.98, 107.99, 120.91, 130.88, 135.34, 136.75, 140.99, 144.12, 149.96, 156.12.

[0022] An imidazo[4,5-g]quinoline-2-one compound and its use as an agricultural insecticide for controlling insect pests.

[0023] The imidazo[4,5-g]quinoline-2-one compound described in the present invention has excellent insecticidal activity. Therefore, the present invention also includes the use of the compound of formula (I) as an agricultural insecticide for controlling diseases.

[0024] The invention discloses an insecticidal composition comprising the imidazo[4,5-g]quinoline-2-one compound as an active component and an insecticidal composition of the imidazo[4,5-g]quinoline-2-one compound, propylene glycol and sulfoxaflor.

[0025] Preferably, the mass ratio of the imidazo[4,5-g]quinoline-2-one compound to propylene and sulfoxaflor is (1-10):(1-10):(1-10).

[0026] Under the preferred mass ratio, the combination of the imidazo[4,5-g]quinoline-2-one compound, propylene and sulfoxaflor has a very obvious synergistic effect, has excellent control effects on piercing-sucking and sucking pests, and can significantly prolong the effective period.

[0027] The present invention also provides an insecticide, comprising the above pesticide composition.

[0028] Preferably, the insecticide further comprises an adjuvant, and the content of the effective component in the insecticide composition is 2-70 wt%.

[0029] The above preferred content is conducive to obtaining a higher control effect with a lower pesticide dosage.

[0030] Preferably, the auxiliary agent includes at least one of a solubilizer, a dispersant, a wetting agent, a defoamer, a disintegrant, a thickener or a filler.

[0031] Optionally, the formulation of the compound composition is water dispersible granules, suspensions, microemulsions, aqueous emulsions, emulsifiable concentrates and wettable powders.

[0032] Compared with the prior art, the beneficial effects of the present invention are as follows.

[0033] The compound of the invention exhibits excellent insecticidal effect. During the synthesis process, the synthesis steps are simplified, the reaction conditions are optimized, and the possibility of future industrial production is provided.

[0034] At the same time, when combined with the existing insecticides sulfoxaflor and propidium pyraclostrobin, it has a significant synergistic effect, has excellent control effects on piercing-sucking and sucking pests, and can significantly prolong the effective period.

[0035] Obviously, according to the above contents of the present invention, in accordance with the common technical knowledge and means in the art, without departing from the above basic technical ideas of the present invention, other various forms of modification, replacement or change may be made. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 : Indoor efficacy test of the compound obtained by the present invention on cotton aphid. DETAILED DESCRIPTION

[0037] The following synthetic examples and biological test results can be used to further illustrate the present invention, but are not meant to limit the present invention.

[0038] Synthesis Example

[0039] Example 1. Preparation of Compound 5

[0040] (1) Synthesis of compound 3

[0041]

[0042] 150 ml of ethanol was added to the reaction bottle, and then 15.9 g of quinoline-6,7-diamine (Compound 1) was added. After stirring and dissolving, 20 g of potassium hydroxide was added. After stirring for 10 minutes, 17.4 g of ethyl 4-methyl-3-oxopentanoate (Compound 2) was slowly added dropwise to the system. After the addition was complete, the reaction was stirred at room temperature for 2 hours. After the reaction was completed under TLC monitoring, the reaction solution was concentrated, and the concentrated reaction solution was added to water. After crystallization, it was stirred for half an hour, filtered, and the filter cake was washed with water. It was dried at 50°C for 2 hours to obtain a light yellow solid 1-(3-methyl-1-butene-2-yl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (Compound 3), 21.0 g, yield: 83.0%.

[0043] 1 H-NMR (400 MHz, CDCl3) δ: 1.15(d, 6H), 2.38(m, 1H), 4.35(d, 2H), 6.49(d, 1H), 7.11(m, 1H), 7.90(m, 1H), 7.99(s, 1H), 8.52(m, 1H), 9.10(s, 1H). 13 C-NMR (125 MHz, CDCl3) δ: 21.06, 30.91, 98.04, 104.15, 107.99, 120.86, 129.93, 130.30, 135.39, 135.89, 140.28, 145.54, 149.59, 153.37.

[0044] LC-MS(ESI, pos, ion) m / z: 254.12[M+H].

[0045] (2) Synthesis of compound 4

[0046]

[0047] 20 g of compound 3 was added to 200 ml of DMF, and 20 g of sodium hydroxide was added. The mixture was stirred for half an hour, and 8.21 g of 1,2-dichloroethane was added dropwise. After the addition was complete, the mixture was stirred at room temperature for 10 hours. After the reaction was completed under TLC monitoring, the reaction solution was concentrated in a vacuum at below 70°C to a quarter of the original volume. The remaining system was poured into cold water, stirred for crystallization for 1 hour, filtered, and dried in a vacuum at 50°C to obtain an off-white solid 3-(2-chloroethyl)-1-(3-methyl-1-butene-2-yl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one, 21.6 g, with a yield of 86.5%.

[0048] 1H-NMR (400 MHz, CDCl3) δ: 1.16(d, 6H), 2.37(m, 1H), 3.21(t, 2H), 3.67(t, 2H), 4.35(d, 2H), 6.48(s, 1H), 7.10(m, 1H), 7.90(m, 1H), 7.99(s, 1H),8.52(m, 1H). 13 C-NMR (125 MHz, CDCl3) δ:21.06,30.91,42.21,42.66,95.64,99.93,107.96,120.90,130.06,133.51,135.30,140.56,144.22 ,149.56,156.19.

[0049] LC-MS(ESI, pos, ion) m / z: 316.11[M+H].

[0050] (3) Synthesis of compound 5

[0051]

[0052] 20 g of compound 4 was added to 200 ml of tetrahydrofuran, and 20 g of sodium hydroxide and 5.4 g of tetrahydropyrrole were added. The mixture was stirred at room temperature for 4 hours. After the reaction was completed under TLC monitoring, the mixture was concentrated in vacuo below 70°C until no more liquid flowed out. The residue was separated by flash column chromatography to obtain an off-white solid of 1-(3-methyl-1-butene-2-yl)-3-(2-(pyrrolidin-1-yl)ethyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (compound 5), 20.2 g, yield: 91.0%.

[0053] 1 H-NMR (400 MHz, CDCl3) δ: 1.16(d, 6H), 1.82(m, 4H), 2.37(m, 1H), 2.60(m, 4H), 3.20(t, 2H), 3.41(t, 2H), 4.36(s, 2H), 6.49(d, 1H), 7.10(m, 1H),7.89(m, 1H), 7.99(s, 1H), 8.54(m, 1H). 13C-NMR (125 MHz, CDCl3) δ: 21.06, 23.70, 30.91, 40.21, 54.03, 56.51, 95.64, 99.93, 107.96, 120.90, 130.06, 133.51, 135.30, 140.56, 144.22, 149.56, 156.19.

[0054] LC-MS(ESI, pos, ion) m / z: 351.46[M+H].

[0055] Example 2, Synthesis of Compound 6

[0056]

[0057] 20 g of compound 4 was added to 200 ml of tetrahydrofuran, and 20 g of sodium hydroxide and 10.6 g of 3-trifluoromethyltetrahydropyrrole were added. The mixture was stirred at room temperature for 4 hours. After the reaction was completed under TLC monitoring, the mixture was concentrated under vacuum below 70°C until no more liquid flowed out. The residue was separated by flash column chromatography to obtain an off-white solid 1-(3-methyl-1-butene-2-yl)-3-(2-(3-trifluoromethylpyrrolidin-1-yl)ethyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (compound 6), 23.7 g, yield: 89.3%.

[0058] 1 H-NMR (400 MHz, CDCl3) δ: 1.14(dd, 6H), 1.42(m, 1H), 1.65(m, 1H), 2.27-2.44(m, 4H), 2.62(t, 2H), 2.87(m, 1H), 3.08(m, 1H), 3.41(t, 2H), 4.35(s,2H), 6.49(s, 1H), 7.11(m, 1H), 7.90(d, 1H), 7.99(s, 1H), 8.54(m, 1H). 13 C-NMR (125 MHz, CDCl3) δ: 21.06, 30.91, 33.48, 40.21, 45.38, 53.23, 56.86, 61.97, 95.64, 99.93, 107.96, 120.90, 130.06, 133.51, 135.30, 140.56, 144.08, 149.56, 156.19.

[0059] LC-MS(ESI, pos, ion) m / z: 419.20[M+H].

[0060] Example 3, Synthesis of Compound 7

[0061]

[0062] 20 g of compound 4 was added to 200 ml of tetrahydrofuran, and 20 g of sodium hydroxide and 11.8 g of 3-trifluoromethoxytetrahydropyrrole were added. The mixture was stirred at room temperature for 4 hours. After the reaction was completed under TLC monitoring, the mixture was concentrated under vacuum below 70°C until no more liquid flowed out. The residue was separated by flash column chromatography to obtain an off-white solid of 1-(3-methyl-1-butene-2-yl)-3-(2-(3-trifluoromethoxypyrrolidin-1-yl)ethyl)-1,3-dihydro-2H-imidazo[4,5-g]quinolin-2-one (compound 7), 25.7 g, yield: 93.4%.

[0063] 1 H-NMR (400 MHz, CDCl3) δ: 1.15(dd, 6H), 1.69(m, 1H), 2.19(m, 2H), 2.39(m, 2H), 2.62(t, 3H), 2.99(m, 1H), 3.41(t, 2H), 3.88(m, 1H), 4.35(s, 2H), 6.49(s, 1H), 7.11(m, 1H), 7.90(d, 1H), 7.99(s, 1H), 8.52(m, 1H). 13 C-NMR (125MHz, CDCl3) δ: 21.06, 30.91, 35.59, 40.24, 50.52, 56.93, 60.94, 77.31, 95.64, 99.98, 107.99, 120.91, 130.88, 135.34, 136.75, 140.99, 144.12, 149.96, 156.12.

[0064] LC-MS(ESI, pos, ion) m / z: 435.19[M+H].

[0065] Test Example 1: Indoor efficacy test of the compound obtained in the present invention against cotton aphid

[0066] Aphidopim was used as a positive control. The test subjects were cotton aphids (Aphis gossypii Glover), and the test conditions were set as temperature: 23℃-25℃; relative humidity: 60%-70%; light: 14h light, 10h dark; the test method was the insect-carrying leaf immersion method. The treated test insects were cultured in the aforementioned test environment, and the test insects were observed one day after different concentrations of compound 5, compound 6 and compound 7, and the number of dead insects was checked to calculate the mortality rate, LC 50 and LC 90 , convert the test concentration into a logarithmic value, convert the mortality rate into a probability value, and obtain the linear regression equation (y = a + bx), LC 50 Value, LC 95 The values ​​and 95% confidence intervals were calculated. Insects that could not turn over and crawl normally were considered dead.

[0067] Depend on Figure 1 It can be seen that the compounds 5, 6 and 7 obtained in the present invention all have good insecticidal effects, among which the insecticidal effects of compounds 6 and 7 are better than those of diprofenoprene.

[0068] Test Example 2: Indoor efficacy test of the compound obtained by the present invention combined with abicyclopyrin and sulfoxaflor against cotton aphids

[0069] The test subjects were cotton aphids, and the test conditions were set at 23℃-25℃; relative humidity: 60%-70%; light: 14h light, 10h dark; the test method was the insect-carrying leaf immersion method. The treated test insects were cultured in the aforementioned test environment, and the test insects were observed one day after the combination of different concentrations of compound 7 and diprofenopterin and sulfoxaflor. The number of dead insects was checked, and the mortality rate, LC 50 and LC 90 , convert the test concentration into a logarithmic value, convert the mortality rate into a probability value, and obtain the linear regression equation (y = a + bx), LC 50 Value, LC 95 The values ​​and 95% confidence intervals were calculated. Insects that could not turn over and crawl normally were considered dead.

[0070] The evaluation method adopts the co-toxicity coefficient method.

[0071] Single-dose toxicity index = standard drug LC 50 / Test reagent LC 50 ×100

[0072] Measured toxicity index ATI = standard agent LC 50 / Mixed LC 50 ×100

[0073] Theoretical toxicity index TTI = toxicity index of A × content of A in the mixture (%) + toxicity index of B × content of B in the mixture (%) + toxicity index of C × content of C in the mixture (%)

[0074] Co-toxicity coefficient CTC = ATI / TTI × 100

[0075] A co-toxicity coefficient greater than 80 indicates a synergistic effect, a co-toxicity coefficient less than 80 indicates an antagonistic effect, and a co-toxicity coefficient between 80 and 120 indicates an additive effect.

[0076] Test results: The evaluation of the combined effects of compound 7 obtained in the present invention and acyclovir and sulfoxaflor on cotton aphid is shown in Table 1.

[0077] Table 1

[0078]

[0079] As shown in Table 1, compound 7, sulfoxaflor and sulfoxaflor have good insecticidal activity against cotton aphids, and most of the three have synergistic effects after being mixed. Among them, the compound ratios of 5:1:1, 10:1:1 and 10:1:10 have good synergistic effects. It also shows that when the ratio of the compounds obtained in the present invention is high, the synergistic effect is the best.

[0080] Test Example 3: Storage stability test

[0081] Room temperature stability test: The synergistic insecticidal composition prepared in Example 2 was placed at room temperature 23±2°C for 3 days, and the appearance was observed for changes. The grades were evaluated: A: no stratification, no turbidity, B: no stratification, slight turbidity, C: slight stratification, obvious turbidity, D: obvious stratification, obvious turbidity. The results are shown in Table 2.

[0082] Low temperature stability test: According to GB / T 19137-2003 "Test method for low temperature stability of pesticides", the synergistic insecticidal composition prepared in Example 2 was placed at 0±2°C for 3 days, and the appearance was observed for changes and the grades were evaluated: A: no stratification, no turbidity, B: no stratification, slight turbidity, C: slight stratification, obvious turbidity, D: obvious stratification, obvious turbidity. The results are shown in Table 2.

[0083] Dilution stability test: Based on MT185, the synergistic insecticidal composition prepared in Example 2 was diluted with conventional hard water at a prescribed ratio, and the content percentage of particles with a diameter less than 25 μm was measured. The results are shown in Table 2.

[0084] Table 2

[0085]

[0086] As can be seen from Table 2, the compound obtained in the present invention is compounded with acyclovir and sulfoxaflor, which enhances the mutual solubility and storage stability of the active ingredients and adjuvants, and is not prone to precipitation and stratification during long-term storage.

[0087] In summary, the compound obtained in the present invention has good insecticidal effect, and when used in combination with sulfoxaflor and sulfoxaflor, it has an excellent synergistic effect, and is an insecticide composition worthy of promotion.

Claims

1. An imidazo[4,5-g]quinoline-2-one compound, the general chemical structure of which is shown in Formula I, Wherein R is selected from H, OCF3, or CF3.

2. A method for synthesizing an imidazo[4,5-g]quinoline-2-one compound of formula I as claimed in claim 1, characterized in that: The route of the synthesis method is:

3. Use of the imidazo[4,5-g]quinoline-2-one compound as claimed in claim 1 in the preparation of insecticides.

4. The use of the imidazo[4,5-g]quinoline-2-one compound according to claim 3, characterized in that: Used for preparing an application for preventing and controlling piercing-sucking and sucking pests on crops.

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