A arecoline ester derivative, and a preparation method and application thereof

Abstract

The application discloses an arecoline ester derivative, a preparation method and application thereof, relates to the technical field of chemical pesticides, and has a brand-new molecular structure, and the bacteriostatic activity and insecticidal activity of the arecoline ester derivative are significantly enhanced compared with arecoline; the arecoline ester derivative has certain inhibiting effects on Puccinia recondita, Diplodia natalensis, Gibberella saubinetii, Pyricularia grisea, Phomopsis vexans, Physalospora piricola, Pestalotiopsis versiflorea, and Colletotrichum gloeosporioides; and the arecoline ester derivative also has certain insecticidal activity on Aedes aegypti larvae.

Description

Technical Field

[0001] This invention relates to the technical field of chemical pesticides, and more specifically, to an arecoline ester derivative, its preparation method, and its application. Background Technology

[0002] Using natural products as lead compounds for structural modification and derivation is the main strategy for developing new pesticides at present. Plant-derived natural products have the characteristics of being easily degradable in nature, having low toxicity to crops, and low residues, which are in line with the current development trend of green pesticides.

[0003] Arecoline is the main active substance in the areca nut, a palm tree. It has a paralyzing effect on the nervous system, thus exhibiting some insecticidal activity in agriculture, and also possesses antimicrobial properties. Current research indicates that arecoline is effective against tapeworms (…). Dipylidium caninum ), Oncomelania ( Oncomelania hupensis Gredler and blowflies ( Calliphora vicinal Maggots have a certain degree of activity and are effective against third-instar larvae of the diamondback moth (LC). 50 The concentration was 64.62 mg / L. Meanwhile, arecoline is effective against Staphylococcus aureus (…). Staphylococcus aureus Bacillus subtilis ( Bacillus subtle ), Bacillus cereus ( Bacillus cereus ), Escherichia coli ( Escherichia coli All of them have inhibitory effects, with minimum inhibitory concentrations of 12.50 mg / mL against Staphylococcus aureus and Bacillus subtilis, respectively. Summary of the Invention

[0004] In view of the above-mentioned technical problems in related technologies, the present invention provides an arecoline ester derivative, its preparation method and application, which can solve the above problems.

[0005] To achieve the above-mentioned technical objectives, the technical solution of the present invention is implemented as follows:

[0006] A arecoline ester derivative, the structural formula of which is shown in formula (I):

[0007]

[0008] In formula (Ⅰ):

[0009] X is selected from S or O;

[0010] m can be 0, 1, 2, or 3;

[0011] R is selected from R 1 For substituent aromatic rings, R 2 Alicyclic compounds containing substituents, R 3For substituent-containing oxygen heterocycles, R 4 It is a nitrogen heterocycle containing substituents, R 5 It is a substituent-containing sulfur heterocycle, R 6 For substituent-containing aromatic heterocycles, R 7 R is a benzo[a]heterocyclic ring containing substituents. 8 It is a polycyclic aromatic hydrocarbon containing substituents.

[0012] Furthermore, in equation (Ⅰ), R is selected from R 1 For N 1 Substituted aromatic rings, R 2 For N 2 Substituted alicyclic ring, R 3 For N 3 Substituted oxygen heterocycles, R 4 For N 4 Substituted nitrogen heterocycles, R 5 For N 5 Substituted sulfur heterocycles, R 6 For N 6 Substituted aromatic heterocycles, R 7 For N 7 Substituted benzo[a]heterocyclic ring, R 8 For N 8 Substituted polycyclic aromatic hydrocarbons.

[0013] Furthermore, N 1 Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group, C1-C6 alkylsulfonyl group, halo-C1-C6 alkylsulfonyl group, di(C1-C6 alkyl)aminosulfonyl group, halo-di(C1-C6 alkyl)aminosulfonyl group, C1-C6 alkylsulfonyloxy group, halo-C1-C6 alkylsulfonyloxy group; N 2Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C3-C6 cycloalkyl group, halo-C3-C6 cycloalkyl group, C2-C6 alkenyl group, halo-C2-C6 alkenyl group, C2-C6 alkenoxy group, halo-C2-C6 alkenoxy group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group; N 3 Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group; N 4 Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group; N 5 Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group, C1-C6 alkylthio group, halo-C1-C6 alkylthio group, C1-C6 olefin thio group, and halo-C1-C6 olefin thio group; N 6Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group; N 7 Selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, halo-di(C1-C6 alkyl)aminocarbonyl group; N 8 It is selected from one or more of the following: hydrogen atom, halogen atom, cyano group, amino group, hydroxyl group, C1-C6 alkyl group, halo-C1-C6 alkyl group, C1-C6 alkoxy group, halo-C1-C6 alkoxy group, C1-C6 alkylamino group, halo-C1-C6 alkylamino group, di(C1-C6 alkyl)amino group, halo-di(C1-C6 alkyl)amino group, C1-C6 alkoxycarbonyl group, halo-C1-C6 alkoxycarbonyl group, C1-C6 alkylaminocarbonyl group, halo-C1-C6 alkylaminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, and halo-di(C1-C6 alkyl)aminocarbonyl group.

[0014] A method for preparing arecoline ester derivatives,

[0015]

[0016] The reaction is carried out by compounds represented by general formulas II, III, and IV, and the specific reaction steps include:

[0017] S1. Under anhydrous conditions, add compound II and thionyl chloride into a round-bottom flask, reflux until the solid is completely dissolved, remove excess thionyl chloride to obtain a white solid compound III, and proceed directly to the next step of the reaction without purification;

[0018] S2. The compound of formula III, the acid-binding agent, the compound of formula IV, and the organic solvent are reacted at -5~50℃, and the reaction is monitored by TLC. After the reaction is completed, the compound of formula I is obtained by extraction, concentration, and silica gel column chromatography.

[0019] Furthermore, the acid-binding agent is one or more of triethylamine, pyridine, N,N-diisopropylethylamine, 1-methylpyridine, sodium acetate, potassium carbonate, and sodium hydroxide; the organic solvent is one or more of dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, methanol, ethanol, petroleum ether, n-butanol, benzene, toluene, xylene, diethyl ether, and tetrahydrofuran.

[0020] Application of an arecoline ester derivative, wherein the arecoline ester derivative is used in bactericidal and insecticidal compositions.

[0021] Furthermore, the bactericidal composition includes at least one of the arecoline ester derivatives and is used as an agricultural bactericide, wherein the arecoline ester derivative has a mass fraction of 1 to 99.9% in the bactericidal composition.

[0022] Furthermore, the formulation of the agricultural fungicide is at least one of emulsifiable concentrate, water-in-oil emulsion, microemulsion, wettable powder, water-dispersible granule, and suspension concentrate. The agricultural fungicide is used to control plant pathogenic fungi, including: Oomycetes, such as Peronosporales (downy mildew) and White Rust (white rust). White ), damping-off bacteria ( Pythium ), cottony rot fungus ( Achlya Phytophthora ( ) Phytophthora Late blight pathogen ( Phytophthora Basidiomycotina, such as rust fungi (Uredinales) and smut fungi (Ustilaginales); Ascomycotina, such as powdery mildew fungi (Erysiphales) and black spot fungi (… Ceratocystis ),anthrax( Glomerulus Fusarium head blight ( Gibberella ), ergot ( Harpsichord ), Sclerotinia sclerotiorum ( Sclerotinia ), black spot bacterium ( Ventura ), ; Deuteromycotina, such as brown rot fungi ( Necklaces ), powdery mildew ( Oedipus ), rice blast fungus ( Firefly ), Penicillium ( Penicillium Verticillium wilt ( Verticillium wilt ), brown spot bacteria ( Cercospora ), ring spot bacteria ( Alternaria ), black mold fungus ( Cladosporium ), damping-off fungus ( Rhizectomy ), white rot fungus ( Scarotium Fusarium head blight ( Fusarium Anthrax bacteria ( Colletotrichum ) *Pseudomonas syringae* ( Pestalotiopsis ), Pseudomonas stolonifera ( Phomopsis ), Diplodia (a fungus that causes stem rot), etc.

[0023] Furthermore, the selected plant pathogenic fungi are one or more of the following: *Magnaporthe oryzae* (rice blast fungus), *Botryodipladiatheobromae* (mango stem rot fungus), *Fusarium verticillioides* (wheat stem rot fungus), *Bothryosphaeria dothidea* (apple ring rot fungus), *Colletotrichum gloeosporioides* (mango anthracnose fungus), *Rhizoctonia solani* (rice sheath blight fungus), *Diaporthe ambigua* (stem spot fungus), *Pseudopestalotiopsis theae* (tea polychaete fungus), and *Phytophthora capsici* (pepper rot fungus).

[0024] Furthermore, the insecticidal composition includes at least one of the arecoline ester derivatives and is used as an agricultural insecticide, wherein the arecoline ester derivative has a mass fraction of 1 to 99.9% in the insecticidal composition.

[0025] Furthermore, the formulation of the agricultural insecticide is at least one of emulsifiable concentrate, water-in-oil emulsion, microemulsion, wettable powder, water-dispersible granules, and suspension concentrate. The agricultural insecticide is used to control pests or mites, including: Lepidoptera, Homoptera, Thysanoptera, and Arachnoidea.

[0026] Furthermore, the selected pest or mite was Aedes aegypti (… Aedes aegypti larvae, diamondback moth ( Small xylostella One or more of the larvae.

[0027] The beneficial effects of this invention are as follows: The arecoline ester derivatives provided by this invention have a novel molecular structure, and their antibacterial and insecticidal activities are significantly enhanced compared with arecoline. They have certain inhibitory effects on virucidal fungi, mango stem rot fungi, wheat scab fungi, rice sheath blight fungi, pseudostem mold fungi, apple ring rot fungi, tea polychaete fungi, mango anthracnose fungi, and pepper phytophthora. At the same time, they show certain insecticidal activity against Aedes aegypti mosquito larvae. Detailed Implementation

[0028] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art are within the scope of protection of the present invention.

[0029] Example 1:

[0030] The structural formula of the arecoline ester derivative in this embodiment is shown in I-1 below:

[0031]

[0032] Its synthesis method is as follows:

[0033] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0034] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0035] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0036] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, and SOCl2 (5 mL) was added. The mixture was heated to reflux and the reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0037] Step 3: Preparation of Compound I-1

[0038] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 3,5-dichlorothiophenol (0.269 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) to obtain a yellow oily liquid in 67.5% yield.

[0039] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.40 (t, J = 1.9 Hz, 1H), 7.33 (d, J = 1.9 Hz, 2H), 7.18 – 7.10 (m, 1H), 3.22 – 3.16 (m, 2H), 2.55 (m,2H), 2.51 – 2.43 (m, 2H), 2.41 (s,3H).

[0040] Example 2:

[0041] The structural formula of the arecoline ester derivative in this embodiment is shown in I-12 below:

[0042]

[0043] Its synthesis method is as follows:

[0044] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0045] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixed solution was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0046] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0047] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0048] Step 3: Preparation of Compound I-12

[0049] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 4-methylthiothiophene-2-thiol (0.245 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) to obtain a yellow oily liquid in 60.1% yield.

[0050] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.22 – 7.14 (m, 1H),7.12 – 7.03 (m, 1H), 6.87 – 6.60 (m, 1H), 3.86 – 3.47 (m, 2H), 2.85 – 2.78(m, 2H),2.47 (s, 2H), 2.31 (s, 3H), 2.29 – 2.13 (m, 2H).

[0051] Example 3:

[0052] The structural formula of the arecoline ester derivative of this embodiment is shown in I-25 below:

[0053]

[0054] Its synthesis method is as follows:

[0055] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0056] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixed solution was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0057] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0058] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0059] Step 3: Preparation of Compound I-25

[0060] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 2-methanethiol-5-trifluoromethylpyridine (0.269 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) to obtain a yellow solid in 58.9% yield.

[0061] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.53 (d, J = 1.9 Hz, 1H),7.55 – 7.50 (m, 1H), 7.37 (d, J = 6.4 Hz, 1H), 6.78 – 6.72 (m, 1H), 4.37 (s,1H), 3.22 – 3.16 (m, 2H), 2.85 – 2.78 (m, 2H), 2.31 (s, 3H), 2.28 – 2.14 (m,2H).

[0062] Example 4:

[0063] The structural formula of the arecoline ester derivative in this embodiment is shown in I-29 below:

[0064]

[0065] Its synthesis method is as follows:

[0066] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0067] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixed solution was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0068] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0069] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0070] Step 3: Preparation of Compound I-29

[0071] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 7-fluoro-4-methylthiol quinazoline (0.293 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) to obtain a yellow oily liquid in 55.2% yield.

[0072] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 9.19 (s, 1H), 8.12 –8.05 (m, 1H), 7.46 – 7.40 (m, 1H), 7.18 – 7.10 (m, 1H),6.78 – 6.72 (m, 1H),4.61 (s, 2H), 3.22 – 3.16 (m, 2H), 2.85 – 2.78 (m, 2H), 2.31 (s, 3H), 2.28 –2.14 (m, 2H).

[0073] Example 5:

[0074] The structural formula of the arecoline ester derivative in this embodiment is shown in I-38 below:

[0075]

[0076] Its synthesis method is as follows:

[0077] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0078] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to give a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to give white flaky crystals of arecoline in 86% yield.

[0079] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0080] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0081] Step 3: Preparation of Compound I-38

[0082] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 4-methylthiol quinazoline (0.264 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 4:1) to obtain a yellow oily liquid in 69.1% yield.

[0083] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.60 (d, J = 1.8 Hz, 1H), 7.39 (d, J = 1.6 Hz, 1H), 6.78 – 6.72 (m, 1H), 3.38 – 3.32 (m, 2H), 3.22 – 3.16(m, 2H), 3.14 – 3.08 (m, 2H), 2.85 – 2.78 (m, 2H), 2.28 – 2.14 (m, 2H).

[0084] Example 6:

[0085] The structural formula of the arecoline ester derivative of this embodiment is shown in I-59 below:

[0086]

[0087] Its synthesis method is as follows:

[0088] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0089] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to give a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to give white flaky crystals of arecoline in 86% yield.

[0090] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0091] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0092] Step 3: Preparation of Compound I-59

[0093] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 3-methylnaphthalene-2-ol (0.239 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate) to obtain a yellow oily liquid in 69.7% yield.

[0094] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.77 – 7.67 (m, 2H),7.65 – 7.61 (m, 1H), 7.50 – 7.42 (m, 3H), 6.73 – 6.68 (m, 1H), 3.22 – 3.16(m, 2H), 2.84 –2.75 (m, 2H), 2.32 (s, 3H), 2.31 (s, 3H), 2.29 – 2.16 (m, 2H).

[0095] Example 7:

[0096] The structural formula of the arecoline ester derivative in this embodiment is shown in I-61 below:

[0097]

[0098] Its synthesis method is as follows:

[0099] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0100] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0101] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0102] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0103] Step 3: Preparation of Compound I-61

[0104] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 5-cyano-2-hydroxypyrimidine (0.186 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate) to obtain a yellow oily liquid in 71.1% yield.

[0105] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.77 (s, 2H), 6.74 –6.68 (m, 1H), 3.73 – 3.51 (m, 2H), 2.84 – 2.75 (m, 2H), 2.31 (s, 3H), 2.29 –2.16 (m,2H).

[0106] Example 8:

[0107] The structural formula of the arecoline ester derivative in this embodiment is shown in I-65 below:

[0108]

[0109] Its synthesis method is as follows:

[0110] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoline)

[0111] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0112] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0113] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0114] Step 3: Preparation of Compound I-65

[0115] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 3-phenoxybenzyl alcohol (0.300 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate) to obtain a yellow oily liquid in 70.4% yield.

[0116] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ7.39 – 7.32 (m, 2H),7.30 – 7.23 (m, 0H), 7.14 – 7.03 (m, 2H), 7.02 – 6.96 (m, 2H),6.95 – 6.89 (m,1H), 6.88 – 6.83 (m, 1H), 6.74 (tt, J = 4.4, 1.0 Hz, 1H), 5.18 (t, J = 1.0 Hz,2H), 3.22 – 3.16 (m, 2H), 2.84 – 2.75 (m, 2H), 2.31 (s, 3H), 2.29 – 2.16 (m,2H).

[0117] Example 9:

[0118] The structural formula of the arecoline ester derivative in this embodiment is shown in I-89 below:

[0119]

[0120] Its synthesis method is as follows:

[0121] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0122] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to give a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to give white flaky crystals of arecoline in 86% yield.

[0123] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0124] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0125] Step 3: Preparation of Compound I-89

[0126] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 1,3,4-thiadiazole-2-methanol (0.174 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate) to obtain a yellow oily liquid in 65.5% yield.

[0127] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.88 (s, 1H), 6.77 –6.71 (m, 1H), 5.93 – 5.18 (m, 2H), 3.84 – 3.31 (m, 2H), 2.83 –2.74 (m, 2H),2.31 (s, 3H), 2.29 – 2.16 (m, 2H).

[0128] Example 10:

[0129] The structural formula of the arecoline ester derivative in this embodiment is shown in I-100 below:

[0130]

[0131] Its synthesis method is as follows:

[0132] Step 1: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid (arecoside)

[0133] 1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester-hydrobromide (arecoline hydrobromide) (2.35 g, 10 mmol) was dissolved in water (30 mL), and the pH was adjusted to 10–11 with 30% Na₂CO₃. The mixture was extracted with CH₂Cl₂ (3 × 30 mL), the organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to obtain a yellow oily substance, which was then refluxed with water (30 mL) for 24 h. After the reaction was complete, the mixture was concentrated under reduced pressure, and the crude product was washed with anhydrous ethanol to obtain white flaky crystals of arecoline, with a yield of 86%.

[0134] Step 2: Preparation of 1-methyl-1,2,5,6-tetrahydropyridine-3-formyl chloride

[0135] Arecoline (0.917 g, 6.5 mmol) was placed in a dry two-necked flask, SOCl2 (5 mL) was added, and the mixture was heated to reflux. The reaction ended after the solid was completely dissolved. Excess SOCl2 was removed under reduced pressure to obtain a powdery white solid, which could be directly used for the next reaction without purification.

[0136] Step 3: Preparation of Compound I-100

[0137] The compound prepared in step two (0.24 g, 1.5 mmol) was placed in anhydrous CH2Cl2, and triethylamine (0.3 mL, 2 mmol) and 4-cyclopropylcyclohexane-1-ol (0.253 g, 1.5 mmol) were added sequentially under ice bath conditions. The reaction was allowed to proceed at room temperature for 0.5 h. After the reaction was complete, saturated NaHCO3 was added to quench the reaction, and the mixture was extracted with CH2Cl2 (3 × 20 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous MgSO4, filtered, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: ethyl acetate) to obtain a yellow oily liquid in 66.3% yield.

[0138] The results of the 1H NMR spectrum are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 6.74 – 6.68 (m, 1H), 4.84 – 4.76 (m, 1H), 3.22 – 3.16 (m, 2H), 2.84 – 2.75 (m, 2H), 2.31 (s, 3H), 2.29 – 2.16 (m, 2H), 2.00 – 1.90 (m, 2H), 1.80 – 1.66 (m, 3H), 1.66 – 1.56 (m, 2H), 1.53 – 1.41 (m, 3H), 0.71 – 0.56 (m, 4H).

[0139] Other compounds described in this invention can be prepared using the above method.

[0140] Table 1 lists the structural descriptions of some compounds (Ⅰ-1 to Ⅰ-101) with the structure of Formula I replaced by substituents.

[0141]

[0142]

[0143]

[0144]

[0145] Specific application methods

[0146] Application Example 1

[0147] Antibacterial bioactivity assay:

[0148] The experimental method used was the mycelial growth rate method:

[0149] The tested bacterial strain was *Pseudomonas aeruginosa*, the rice blast fungus. Magnaporthe rice Mango stem rot fungus ( Botryodipladia theobromae ), wheat stem rot fungus ( Fusarium verticillium Apple ring rot fungus ( Bothryosphaeria dothidea Mango anthracnose ( Colletotrichum gloeosporioides Rice sheath blight pathogen ( Rhizoctonia solani ), Pseudomonas stolonifera ( Diaporthe ambiguus ), Tea-shaped Polychaete ( Pseudopestalotiopsis theae ), Phytophthora capsici ( Phytophthora capsicum (Provided by the College of Tropical Agriculture and Forestry, Hainan University)

[0150] The arecoline ester derivative test reagent of the present invention was prepared into a potato dextrose agar medium with a mass concentration of 100 mg / L. Mycelial cakes were collected using a 5 mm diameter punch and inoculated onto potato dextrose agar medium containing the test reagent. A medium containing the same solvent and adjuvants was used as a control. Each group was repeated three times, and colony growth was observed. When the diameter of the blank control colony reached 2 / 3 of the entire plate, the colony diameter was measured vertically and crosswise to calculate the inhibition rate.

[0151] Results Processing

[0152] Inhibition rate (%) = [(average colony diameter of control group - average colony diameter of treatment group) / (average colony diameter of control group - diameter of mycelial cake)] × 100%;

[0153] Based on the inhibition rate against plant pathogenic fungi, five levels are defined: 90≤A≤100%; 80≤B<90%; 70≤C<80%; 60≤D<70%; and E<60%.

[0154] Table 2. Results of antibacterial activity tests of some compounds at a concentration of 100 mg / L.

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161] As shown in Table 2, the arecoline ester derivatives provided by this invention exhibit excellent antifungal activity against plant pathogenic fungi at a concentration of 100 mg / L, with inhibition rates exceeding 60%. They can be used as active ingredients in chemical pesticides for the control of plant pathogens, and can be mixed with other permitted carriers or adjuvants in plant protection to create various formulations usable in agriculture.

[0162] Application Example 2

[0163] Insecticidal bioactivity assay:

[0164] The tested pest was Aedes aegypti ( Aedes aegypti Fourth instar larvae:

[0165] The arecoline ester derivative test agent of the present invention was prepared as a dechlorinated aqueous solution with a mass concentration of 100 mg / L. Thirty fourth-instar larvae of Aedes aegypti were randomly selected and placed in a petri dish containing 10 mL of the drug solution. A dechlorinated aqueous solution containing the same solvent and adjuvants was used as a control. Each group was repeated three times. At 24 h and 48 h of drug treatment, the larvae were gently touched with a needle. If they could not move, they were considered dead. The lethality rate was calculated by counting the dead and surviving larvae.

[0166] Result processing:

[0167] Mortality rate (%) = (Number of dead insects / Total number of insects) × 100%;

[0168] Corrected mortality rate (%) = [(treatment mortality rate - control mortality rate) / (1 - control mortality rate)] × 100%;

[0169] Based on the lethality rate against Aedes aegypti larvae, five levels are defined: 90≤A≤100%; 80≤B<90%; 70≤C<80%; 60≤D<70%; E<60%.

[0170] Table 3 shows the insecticidal activity of some compounds against Aedes aegypti larvae at 100 mg / L.

[0171]

[0172]

[0173]

[0174] As shown in Table 3, the arecoline ester derivatives provided by this invention exhibit excellent insecticidal activity against fourth-instar larvae of Aedes aegypti at a concentration of 100 mg / L, with corrected mortality rates exceeding 60%. They can be used as active ingredients in chemical pesticides for the control of crop pests or mites, and can be mixed with other permitted carriers or adjuvants in plant protection to create various formulations usable in agriculture.

[0175] 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, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A arecoline ester derivative, characterized in that, Its structural formula is shown in equation (Ⅰ): ; Formula (I) is I-1, I-2, I-7, I-11, I-18, I-19, I-21, I-22, I-23, I-24, I-34, I-35, I-36, I-48, I-49, I-54, I-55, I-56, I -65, I-68, I-69, I-70, I-71, I-72, I-73, I-74, I-75, I-77, I-80, I-82, I-83, I-84, I-85, I-92, I-93, I-94, I-96; Where I-1 has an X group of S, m is 0, and R is 3,5-dichlorophenyl; where I-2 has an X group of S, m is 0, and R is 2-CHF2-C6H4; where I-7 has an X group of S, m is 0, and R is 4-OCF3-C6H4; where I-11 has an X group of S, m is 0, and R is 4-OC6H5-C6H4; where I-18 has an X group of S, m is 1, and R is 3-N(C2H5)2-C6H4; where I-19 has an X group of S, m is 1, and R is 4-CH(CH3)2-C6H4; where I-21 has an X group of S, m is 1, and R is 3-CON(CH3)2C6H4; where I-22 has an X group of S... For example, in I-23, the X group is S, m is 1, and R is 4-CF3-C6H4; in I-24, the X group is S, m is 1, and R is 2-OCF3-3-F-C6H3; in I-34, the X group is S, m is 2, and R is 3,5-dichlorophenyl; in I-35, the X group is S, m is 2, and R is 3-Cl-5-Br-C6H3; in I-36, the X group is S, m is 2, and R is 4-CHF2-C6H4; in I-48, the X group is O, m is 0, and R is 2-F-C6H4; in I-49, the X group is O, m is 0, and R is 3-Cl-C6H4. H4; where the X group of I-54 is O, m is 0, and R is 3-CF3-C6H4; where the X group of I-55 is O, m is 0, and R is 4-NH2-C6H4; where the X group of I-56 is O, m is 0, and R is 4-OCF3-C6H4; where the X group of I-65 is O, m is 1, and R is 3-OC6H5-C6H4; where the X group of I-68 is O, m is 1, and R is 2,4-dichlorophenyl; where the X group of I-69 is O, m is 1, and R is 3,5-difluorophenyl; where the X group of I-70 is O, m is 1, and R is 2,4-diaminophenyl; where the X group of I-71 is O, m is 1, and R is 2- Cl-4-F-C6H3; where the X group of I-72 is O, m is 1, and R is 3-Cl-4-F-C6H3; where the X group of I-73 is O, m is 1, and R is 4-Cl-2-F-C6H3; where the X group of I-74 is O, m is 1, and R is 4-Cl-3-F-C6H3; where the X group of I-75 is O, m is 1, and R is 3-COOCF3-C6H4; where the X group of I-77 is O, m is 1, and R is 4-OCF3-C6H4; where the X group of I-80 is O, m is 1, and R is 3-OC6H5-C6H4; where the X group of I-82 is O, m is 2, and R is 3,5-dichlorophenyl;In I-83, the X group is O, m is 2, and R is 4-Cl-3-COOCH3-C6H3; in I-84, the X group is O, m is 2, and R is 3-CF3-C6H4; in I-85, the X group is O, m is 2, and R is 4-OCF3-C6H4; in I-92, the X group is O, m is 3, and R is 3,5-dichlorophenyl; in I-93, the X group is O, m is 3, and R is 2,4-difluorophenyl; in I-94, the X group is O, m is 3, and R is 3-Cl-4-Br-C6H3; and in I-96, the X group is O, m is 3, and R is 2-F-C6H4.

2. The application of the arecoline ester derivatives according to claim 1, characterized in that, The arecoline ester derivatives are used in agricultural bactericidal compositions.

3. The application of the arecoline ester derivatives according to claim 2, characterized in that, The agricultural bactericidal composition includes at least one of the arecoline ester derivatives, wherein the arecoline ester derivative has a mass fraction of 1 to 99.9% in the agricultural bactericidal composition.

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