4-(Cyanomethylene)-3,4-dihydropyridone compounds and their synthesis methods and applications

Abstract

The invention discloses a kind of 4-(cyanomethylene)-3,4-dihydropyridone compounds and its synthesis method and application, the synthetic method is with 1-enoylcyclopropionamide compound and cyanomethyl phosphoric acid diester compound as raw material, organic base is catalyst, is dissolved in organic solvent, carries out intramolecular N-nucleophilic addition, intermolecular condensation, dephosphorylation diester reaction by heating, obtains 4-(cyanomethylene)-3,4-dihydropyridone compounds.The synthetic method of the present invention is wide in raw material sources, simple and easy to obtain, reaction conditions are mild, product stability is high, yield is good, and the 4-(cyanomethylene)-3,4-dihydropyridone compounds obtained have excellent insecticidal activity, have good application prospect in the field of insecticides.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic compound synthesis, and in particular relates to a 4-(cyanomethylene)-3,4-dihydropyridone compound, a synthesis method and an application thereof. Background Art

[0002] In the 1970s, based on computational chemistry and structural design methods, scholars obtained a very effective nicotinoid insecticide ingredient - nitrobenzene. However, due to its defect of being easily decomposed by light, later researchers successively developed different generations of neonicotinoid insecticides based on it: imidacloprid 1, imidacloprid 2, thiamethoxam 3, and nitenpyram 4. The evolution of nicotinoid insecticides and the structural formula of neonicotinoid insecticides are shown below.

[0003]

[0004] From the evolution of nicotine insecticides and the structural analysis of neonicotinoid insecticides, it was found that most compounds contain the X structure and Y structure of C=C-NO2 or C=N-NO2(CN), and the Y structure is a heterocyclic structure or a chain structure.

[0005] Neonicotinoid insecticides are currently the most widely used insecticides in agriculture and forestry. Their core mechanism of action is to interfere with nicotinic acetylcholine receptors (nAChRs) in the insect nervous system, causing blockage of nerve conduction, ultimately leading to paralysis and death. Neonicotinoid insecticides boast high insecticidal efficacy, a broad spectrum of activity, low toxicity to non-target organisms, no cross-resistance with traditional insecticides (such as carbamates, organophosphates, cyclopentadiene, and pyrethroids), good plant systemicity, a novel mechanism of action, and high environmental compatibility. They are particularly effective against piercing-sucking pests (such as aphids and leafhoppers). Consequently, these insecticides have gained widespread use worldwide. However, their widespread use has gradually exposed two major issues: first, they cause considerable environmental damage; second, pest resistance to these neonicotinoid insecticides has steadily increased, significantly reducing their effectiveness. Consequently, there is an urgent need for less toxic, more effective alternatives. Summary of the Invention

[0006] To solve the above problems, the present invention aims to provide a 4-(cyanomethylene)-3,4-dihydropyridone compound, which has a structure highly similar to that of neonicotinoid insecticides, and has a C=C-CN group similar to the X structure in most neonicotinoid insecticides in Formula 1 above, and a heterocyclic skeleton (pyridone) in the Y structure; also provides a method for synthesizing the above-mentioned 4-(cyanomethylene)-3,4-dihydropyridone compound; and also provides the application of the above-mentioned 4-(cyanomethylene)-3,4-dihydropyridone compound. The target of neonicotinoid insecticides is the nicotinic acetylcholine receptor. Based on the principle that similar structures tend to act on the same target, the synthesis of the 4-(cyanomethylene)-3,4-dihydropyridone compound provides an innovative direction and alternative species for specific insecticides targeting this target.

[0007] In order to achieve the above-mentioned object of the invention, the present invention adopts the following technical solutions:

[0008] A 4-(cyanomethylene)-3,4-dihydropyridone compound, whose structural formula is:

[0009]

[0010] Among them, Ar 1 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 2-MeC6H4, 2,4-Me2C6H3, 2-ClC6H4, and Bn;

[0011] Ar 2 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 4-ClC6H4, and 2-pyridyl.

[0012] A method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds, comprising using a 1-enoylcyclopropionamide compound A and a cyanomethylphosphodiester compound B as raw materials, an organic base as a catalyst, dissolving the raw materials in an organic solvent, and heating the mixture to carry out intramolecular N-nucleophilic addition, intermolecular condensation, and dephosphodiester reactions to obtain a 4-(cyanomethylene)-3,4-dihydropyridone compound C.

[0013] The reaction route is as follows:

[0014]

[0015] Among them, Ar 1 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 2-MeC6H4, 2,4-Me2C6H3, 2-ClC6H4, and Bn;

[0016] Ar2 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 4-ClC6H4, 2-pyridyl;

[0017] R is selected from Et or iPr.

[0018] Furthermore, the molar ratio of the above-mentioned 1-enoylcyclopropionamide compound A and the cyanomethylphosphonic diester compound B is 1:1-1.2, and the usage ratio of the 1-enoylcyclopropionamide compound A, the organic solvent, and the organic base is 1 mmol:6-8 mL:0.5-1.0 mmol.

[0019] Furthermore, the organic base is one of 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, and 1,5-diazabicyclo[4.3.0]-5-nonene.

[0020] Furthermore, the above-mentioned organic solvent is acetonitrile or ethanol.

[0021] Furthermore, the reaction temperature is 60-80°C.

[0022] Furthermore, the above reaction time is 10 to 15 hours.

[0023] Furthermore, in the above-mentioned method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds, the reaction progress is monitored by thin layer chromatography TLC. After the reactant 1-enoylcyclopropionamide compound A completely disappears, water is added to the reaction system to stop the reaction, and then extraction is performed with an extractant, and the organic phases are combined; the organic phases are then dried with a desiccant, filtered, concentrated, and column chromatographed to obtain 4-(cyanomethylene)-3,4-dihydropyridone compound C.

[0024] Furthermore, the above-mentioned extractant is dichloromethane, ethyl acetate or ether.

[0025] Furthermore, the organic phase desiccant is anhydrous sodium sulfate, anhydrous calcium chloride or anhydrous magnesium sulfate.

[0026] Another object of the present invention is to provide a use of a 4-(cyanomethylene)-3,4-dihydropyridone compound in the preparation of insecticides.

[0027] Furthermore, the above-mentioned insecticide is a drug for preventing and controlling aphids, diamondback moths, and Spodoptera litura.

[0028] A method for testing the insecticidal activity of 4-(cyanomethylene)-3,4-dihydropyridone compounds is disclosed. Indoor screening activity experiments are conducted using agricultural pests, and the insecticidal activity of 4-(cyanomethylene)-3,4-dihydropyridone compounds is tested using a feed mixing method. At a screening concentration of 500 μg / mL, compound C exhibits good insecticidal activity, with mortality rates ranging from 50% to 95% against different pests, such as aphids, diamondback moths, and Spodoptera litura.

[0029] Due to the adoption of the above-mentioned technical solution, the present invention has the following advantages:

[0030] The 4-(cyanomethylene)-3,4-dihydropyridone compounds of the present invention are constructed in one step through a series of multifunctionalized 4-(cyanomethylene)-3,4-dihydropyridone compounds through a tandem reaction process of intramolecular N-nucleophilic addition, intermolecular condensation, and dephosphodimethylation.

[0031] The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds of the present invention uses raw materials from a wide range of sources, is simple and easily available, has mild reaction conditions, has diverse structures, is easy to operate, has economical steps, and has high product stability and good yield.

[0032] The 4-(cyanomethylene)-3,4-dihydropyridone compounds of the present invention have excellent insecticidal activity and have important scientific value and practical application prospects in the field of pesticides. They can provide a unique neonicotinoid insecticide for the prevention and control of pests in agricultural production, and provide a rich screening library and design ideas for specific insecticides targeting nicotinic acetylcholine receptors, and have good application prospects in the field of insecticides. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 is the hydrogen spectrum of the target product C1 in Example 1;

[0034] Figure 2 is the carbon spectrum of the target product C1 in Example 1;

[0035] Figure 3 is the hydrogen spectrum of the target product C2 in Example 2;

[0036] Figure 4 is the carbon spectrum of the target product C2 in Example 2;

[0037] Figure 5 is the hydrogen spectrum of the target product C3 in Example 3;

[0038] Figure 6 is the carbon spectrum of the target product C3 in Example 3;

[0039] Figure 7This is the single crystal structure diagram of the target product C7 in Example 7. DETAILED DESCRIPTION

[0040] The present invention will be further described in detail with reference to the following examples; however, the following examples are merely illustrative, and the present invention is not limited to these examples.

[0041] In the following examples, the organic base is selected as follows: DBU is 1,8-diazabicyclo[5.4.0]undec-7-ene, DMAP is 4-dimethylaminopyridine, and DBN is 1,5-diazabicyclo[4.3.0]-5-nonene.

[0042] Example 1

[0043] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A1 (291 mg, 1 mmol), diethyl cyanomethylphosphonate B1 (0.16 mL, 1 mmol), and EtOH (6 mL) were added, followed by the slow addition of DBU (0.15 mL, 1 mmol). The mixture was stirred at 70°C for 12 h. The reaction was monitored by TLC until the complete disappearance of reactant A1. The reaction solution was then poured into ice water and vigorously stirred. The mixture was extracted three times with dichloromethane (3 × 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain 284 mg of the white target product C1 in a 91% yield.

[0044] Specific reaction formula:

[0045]

[0046] Spectral data of compound C1:

[0047] 1 H NMR (CDCl3, 400MHz): δ: 1.08 (q, J = 4.0 Hz, 2H), 1.80 (q, J = 4.0Hz, 2H), 5.61 (s, 1H), 7.07-7.11 (m, 1H), 7.23-7.31 (m, 2H), 7.35 (s, 1H),7.37-7.41 (m, 5H), 7.54-7.56 (m, 2H);

[0048] 13C NMR (CDCl3, 100MHz): δ: 16.4, 29.3, 101.3, 116.2, 120.2, 123.5, 124.8, 128.0, 129.0, 129.1, 130.3, 134.8, 137.3, 139.9, 157.5, 168.8.

[0049] The hydrogen and carbon spectra of compound C1 are shown in Figure 1 、 Figure 2 .

[0050] Compound C1 was tested for insecticidal activity using the feed-drug mixing method on Spodoptera litura. A 10 mg sample of Compound C1 was weighed and dissolved in 2 mL of DMSO (dimethyl sulfoxide) using a 5 mL pipette. Then, 18 mL of an aqueous solution containing 0.1% (w / v) Tween-80 was added and mixed thoroughly to obtain a 500 μg / mL test solution. Results showed a 64% mortality rate after 48 hours.

[0051] Example 2

[0052] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A2 (321 mg, 1 mmol), diethyl cyanomethylphosphonate B1 (0.16 mL, 1 mmol), and EtOH (6 mL) were added, followed by the slow addition of DBU (0.15 mL, 1 mmol). The mixture was stirred at 70°C for 12 h. The reaction was monitored by TLC until the complete disappearance of reactant A2. The reaction solution was then poured into ice water and vigorously stirred. The mixture was extracted three times with ethyl acetate (3 × 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain 301 mg of the white target product C2 in 88% yield.

[0053] Specific reaction formula:

[0054]

[0055] Spectral data of compound C2:

[0056] 1H NMR (CDCl3, 400MHz): δ: 1.06 (d, J = 4.0 Hz, 2H), 1.77 (d, J = 4.0Hz, 2H), 3.75 (s, 3H), 5.60 (s, 1H), 6.81 (d, J = 8.0 Hz, 2H), 7.19 (s, 1H),7.27-7.34 (m, 1H), 7.38-7.44 (m, 4H), 7.55 (q, J = 8.0 Hz, 2H);

[0057] 13 C NMR (CDCl3, 100MHz): δ: 16.3, 29.1, 55.5, 101.2, 114.1, 116.3, 122.3, 123.6, 127.9, 129.0, 130.2, 130.5, 134.9, 139.8, 156.8, 157.6, 168.8.

[0058] The hydrogen and carbon spectra of compound C2 are shown in Figure 3 、 Figure 4 .

[0059] Compound C2 was tested for insecticidal activity using the feed-drug mixing method on Spodoptera litura. A 10 mg sample of Compound C2 was weighed, dissolved in 2 mL of DMSO using a 5 mL pipette, and then added to 18 mL of an aqueous solution containing 0.1% Tween-80. The mixture was thoroughly mixed to obtain a 500 μg / mL test solution. Results showed a 56% mortality rate after 48 hours.

[0060] Example 3

[0061] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A3 (325 mg, 1 mmol), diisopropyl cyanomethylphosphate B2 (0.2 mL, 1 mmol), and EtOH (8 mL) were added. Then, DBU (0.18 mL, 1 mmol) was slowly added, and the mixture was stirred at 60°C for 12 h. The reaction was monitored by TLC until the reactant A3 completely disappeared. The reaction solution was poured into ice water and vigorously stirred. The mixture was extracted three times with dichloromethane (3 × 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the mixture was separated and purified by column chromatography to obtain 280 mg of the white target product C3 in 81% yield.

[0062] Specific reaction formula:

[0063]

[0064] Spectral data of compound C3:

[0065] 1 H NMR (CDCl3, 400MHz): δ: 1.08 (d, J = 4.0 Hz, 2H), 1.78 (d, J = 4.0Hz, 2H), 5.62 (s, 1H), 7.10 (t, J = 8.0 Hz, 1H), 7.24-7.27 (m, 1H), 7.28-7.31(m, 2H), 7.35 (d, J = 8.0 Hz, 2H), 7.39-7.41 (m, 2H), 7.47 (d, J = 8.0 Hz, 2H);

[0066] 13 C NMR (CDCl3, 100MHz): δ: 16.3, 29.3, 101.7, 116.1, 120.3, 124.0, 124.9, 129.0, 129.1, 129.3, 133.4, 136.1, 137.4, 138.4, 157.2, 168.7.

[0067] The hydrogen and carbon spectra of compound C3 are shown in Figure 5 、 Figure 6 .

[0068] Compound C3 was tested for insecticidal activity using the feed-drug mixing method on Plutella xylostella. A 10 mg sample of compound C3 was weighed, dissolved in 2 mL of DMSO using a 5 mL pipette, and then thoroughly mixed with 18 mL of an aqueous solution containing 0.1% Tween-80 to obtain a 500 μg / mL test solution. Results showed an 88% mortality rate after 48 hours.

[0069] Example 4

[0070] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A4 (321 mg, 1 mmol), diethyl cyanomethylphosphonate B1 (0.16 mL, 1 mmol), and CH3CN (6 mL) were added. Then, DBU (0.15 mL, 1 mmol) was slowly added, and the mixture was stirred at 80°C for 15 h. The reaction was monitored by TLC until the reactant A4 completely disappeared. The reaction solution was poured into ice water and vigorously stirred. The mixture was extracted three times with dichloromethane (3 × 10 mL). The organic phases were combined and dried over anhydrous calcium chloride. The solvent was removed by rotary evaporation, and the mixture was separated and purified by column chromatography to obtain 287 mg of the white target product C4 in 84% yield.

[0071] Specific reaction formula:

[0072]

[0073] Spectral data of compound C4:

[0074] 1 H NMR (CDCl3, 400MHz): δ: 1.08 (d, J = 4.0 Hz, 2H), 1.78 (d, J = 4.0Hz, 2H), 3.84 (s, 3H), 5.53 (s, 1H), 6.91 (d, J = 8.0 Hz, 2H), 7.07-7.11 (m,1H), 7.26-7.30 (m, 3H), 7.39 (d, J = 8.0 Hz, 2H), 7.50 (d, J = 8.0 Hz, 2H);

[0075] 13 C NMR (CDCl3, 100MHz): δ: 16.4, 29.3, 55.4, 99.7, 114.5, 116.5, 120.2,121.3, 124.7, 127.6, 129.0, 129.6, 137.4, 139.5, 157.8, 161.4, 169.0.

[0076] Compound C4's insecticidal activity was tested on aphids using the feed-drug mixing method. A 10 mg sample of compound C4 was weighed, dissolved in 2 mL of DMSO using a 5 mL pipette, and then added to 18 mL of an aqueous solution containing 0.1% Tween-80. The mixture was thoroughly mixed to obtain a 500 μg / mL test solution. Results showed a 66% mortality rate after 48 hours.

[0077] Example 5

[0078] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A5 (305 mg, 1 mmol), diethyl cyanomethylphosphonate B1 (0.16 mL, 1 mmol), and CH3CN (8 mL) were added. Then, DBN (0.11 mL, 1 mmol) was slowly added and stirred at 70°C for 14 h. The reaction was monitored by TLC until the complete disappearance of reactant A5. The reaction solution was poured into ice water and vigorously stirred. The mixture was extracted three times with diethyl ether (3 × 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation. The product was separated and purified by column chromatography to obtain 254 mg of the white target product C5 in a yield of 78%.

[0079] Specific reaction formula:

[0080]

[0081] Spectral data of compound C5:

[0082] 1 H NMR (CDCl3, 400MHz): δ: 1.11 (d, J = 4.0 Hz, 2H), 1.82 (d, J = 4.0Hz, 2H), 4.50 (q, J = 16.0 Hz, 2H), 5.64 (s, 1H), 7.02-7.06 (m, 1H), 7.23-7.27 (m, 2H), 7.32-7.43 (m, 8H);

[0083] 13 C NMR (CDCl3, 100MHz): δ: 20.1, 30.7, 51.2, 98.9, 101.3, 119.5, 126.3, 126.9, 127.2, 128.0, 128.5, 128.6, 128.9, 138.1, 138.6, 165.8, 173.0.

[0084] Compound C5 was tested for insecticidal activity using the feed-drug mixing method on Spodoptera litura. A 10 mg sample of Compound C5 was weighed, dissolved in 2 mL of DMSO using a 5 mL pipette, and then added to 18 mL of an aqueous solution containing 0.1% Tween-80. The mixture was thoroughly mixed to obtain a 500 μg / mL test solution. Results showed a 73% mortality rate after 48 hours.

[0085] Example 6

[0086] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A6 (292 mg, 1 mmol), diethyl cyanomethylphosphonate B1 (0.19 mL, 1.2 mmol), and CH3CN (8 mL) were added. Then, DMAP (98 mg, 0.8 mmol) was slowly added, and the mixture was stirred at 80°C for 10 h. The reaction was monitored by TLC until the complete disappearance of reactant A6. The reaction solution was poured into ice water and vigorously stirred. The mixture was extracted three times with dichloromethane (3 × 10 mL). The organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation, and the mixture was separated and purified by column chromatography to obtain 235 mg of the white target product C6 in a yield of 75%.

[0087] Specific reaction formula:

[0088]

[0089] Spectral data of compound C6:

[0090] 1H NMR (CDCl3, 400MHz): δ: 1.06 (d, J = 4.0 Hz, 2H), 1.76 (d, J = 4.0Hz, 2H), 5.72 (s, 1H), 7.07-7.22 (m, 3H), 7.29-7.31 (m, 2H), 7.50-7.64 (m,4H), 8.57-8.59 (m, 1H);

[0091] 13 C NMR (CDCl3, 100MHz): δ: 16.9, 29.5, 101.4, 116.4, 120.2, 120.3, 122.3, 122.9, 124.2, 128.9, 135.5, 136.3, 138.0, 149.8, 154.8, 162.1, 163.2.

[0092] Compound C6 was tested for insecticidal activity using aphids using the feed-drug mixing method. A 10 mg sample of compound C6 was weighed, dissolved in 2 mL of DMSO using a 5 mL pipette, and then added to 18 mL of an aqueous solution containing 0.1% Tween-80. The mixture was thoroughly mixed to obtain a 500 μg / mL test solution. Results showed a 92% mortality rate after 48 hours.

[0093] Example 7

[0094] To a 50 mL pressure bottle, 1-enoylcyclopropionamide compound A7 (325 mg, 1 mmol), diethyl cyanomethylphosphonate B1 (0.16 mL, 1 mmol), and EtOH (8 mL) were added. Then, DBU (0.14 mL, 0.9 mmol) was slowly added, and the mixture was stirred at 70°C for 12 h. The reaction was monitored by TLC until the complete disappearance of reactant A1. The reaction solution was poured into ice water and vigorously stirred. The mixture was extracted three times with dichloromethane (3 × 10 mL). The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation, and the product was separated and purified by column chromatography to obtain 284 mg of the white target product C7 in 82% yield.

[0095] Specific reaction formula:

[0096]

[0097] Spectral data of compound C7:

[0098] 1H NMR (CDCl3, 400MHz): δ: 1.10 (d, J = 4.0 Hz, 2H), 1.80 (d, J = 4.0Hz, 2H), 5.61 (s, 1H), 7.22-7.28 (m, 2H), 7.32-7.35 (m, 2H), 7.36-7.41 (m,4H), 7.54-7.56 (m, 2H);

[0099] 13 C NMR (CDCl3, 100MHz): δ: 16.5, 29.3, 101.4, 121.5, 123.4, 127.9, 129.0, 129.1, 129.9, 130.3, 134.8, 135.9, 140.0, 157.2, 157.5, 168.9.

[0100] The single crystal structure of compound C7 is shown in Figure 7 shown.

[0101] Compound C7 was tested for insecticidal activity against Spodoptera litura using the feed-drug mixing method. A 10 mg sample of compound C6 was weighed, dissolved in 2 mL of DMSO using a 5 mL pipette, and then added to 18 mL of an aqueous solution containing 0.1% Tween-80. The mixture was thoroughly mixed to obtain a 500 μg / mL test solution. The results showed an 82% mortality rate after 48 hours.

[0102] 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 and 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 4-(cyanomethylene)-3,4-dihydropyridone compound, characterized in that: Its structural formula is: Among them, Ar 1 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 2-MeC6H4, 2,4-Me2C6H3, 2-ClC6H4, and Bn; Ar 2 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 4-ClC6H4, and 2-pyridyl.

2. A method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds, characterized by: The method uses 1-enoylcyclopropionamide compound A and cyanomethylphosphodiester compound B as raw materials, an organic base as a catalyst, and is dissolved in an organic solvent. The mixture is heated to carry out intramolecular N-nucleophilic addition, intermolecular condensation, and dephosphodiester reaction to obtain 4-(cyanomethylene)-3,4-dihydropyridone compound C. The reaction route is as follows: Among them, Ar 1 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 2-MeC6H4, 2,4-Me2C6H3, 2-ClC6H4, and Bn; Ar 2 One selected from Ph, 4-MeC6H4, 4-MeOC6H4, 2-MeC6H4, 4-ClC6H4, 2-pyridyl; R is selected from Et or iPr.

3. The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds according to claim 2, characterized in that: The molar ratio of the 1-enoylcyclopropionamide compound A to the cyanomethylphosphonic diester compound B is 1:1-1.2, and the usage ratio of the 1-enoylcyclopropionamide compound A, the organic solvent, and the organic base is 1 mmol:6-8 mL:0.5-1.0 mmol.

4. The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds according to claim 2, characterized in that: The organic base is one of 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine and 1,5-diazabicyclo[4.3.0]-5-nonene.

5. The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds according to claim 2, characterized in that: The organic solvent is acetonitrile or ethanol.

6. The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds according to claim 2, characterized in that: The reaction temperature is 60-80°C.

7. The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds according to claim 2, characterized in that: The reaction time is 10 to 15 hours.

8. The method for synthesizing 4-(cyanomethylene)-3,4-dihydropyridone compounds according to claim 2, characterized in that: The reaction progress was monitored by thin layer chromatography (TLC). After the reactant 1-enoylcyclopropionamide compound A completely disappeared, water was added to the reaction system to stop the reaction, followed by extraction with an extractant, and the organic phases were combined. The organic phases were then dried with a desiccant, filtered, concentrated, and subjected to column chromatography to obtain 4-(cyanomethylene)-3,4-dihydropyridone compound C.

9. Use of the 4-(cyanomethylene)-3,4-dihydropyridone compound according to claim 1 in the preparation of insecticides.

10. The use according to claim 9, characterized in that: The insecticide is a drug for preventing and controlling aphids, diamondback moths and prodenia litura.

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