Preparation method and use of a novel styrene ester insect covalent pheromone
By designing novel styrene ester-based insect covalent pheromones, the problems of short duration of action and drug resistance of traditional pheromones have been solved, achieving highly efficient, low-toxicity, and low-cost pest control.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
- Filing Date
- 2025-11-27
- Publication Date
- 2026-06-02
AI Technical Summary
Existing chemical pesticides have problems such as pesticide resistance, environmental pollution and increased costs in the process of controlling pests, and traditional styrene-based pheromones have short duration of action and weak effects.
We designed and synthesized a novel styrene ester-based insect covalent pheromone that binds to specific amino acid residues of target proteins via covalent bonds, forming an irreversible binding that prolongs the duration of action and improves control efficacy.
It achieves the dual effect of trapping and killing pest populations and disrupting their reproductive balance, reducing the number of locusts and egg density, and reducing environmental pollution and costs.
Smart Images
Figure CN122127233A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to a method for preparing a novel styrene ester-based insect covalent pheromone and its uses, belonging to the technical field of pesticide preparation. Background Technology
[0002] Pest control is a crucial aspect of agricultural and forestry production and the protection of the Earth's ecosystem. Common control methods include the individual application or integrated management of physical, chemical, and biological methods. Currently, agricultural pest control relies heavily on the use of chemical pesticides. However, the widespread and excessive use of chemical pesticides has led to the emergence of pesticide resistance. To achieve effective pest control, it is necessary to increase the dosage or concentration of pesticides, which continuously increases the cost of pesticides and makes control increasingly difficult. The large-scale use of chemical pesticides can also disrupt and imbalance the ecological balance. While controlling pests, it kills a large number of natural enemies of pests, causing secondary pests to proliferate. The environmental pollution caused by the use of chemical pesticides cannot be ignored. Large amounts of pesticide residues remain in crops, soil, rivers, lakes, and seas, and accumulate in humans and other animals through the food chain, causing secondary harm to humans. Therefore, both domestic and international efforts are being made to explore and research new approaches and technologies for pest control. These studies include: (i) Chemical control: developing new, highly efficient, low-toxicity, and low-residue pesticides, but problems such as pesticide resistance and environmental pollution still exist; (ii) Biological control: introducing natural enemies and parasitic microorganisms of pests to establish ecological balance, such as utilizing pathogens like Metarhizium anisopliae and microsporidia, or raising natural enemies like chickens and ducks; (iii) Physical control: reducing the breeding and spread of pests by adjusting planting density, timing, soil moisture, or artificially generating physical factors (temperature, light, electromagnetic waves, etc.) to achieve control requirements; (iv) Pheromone and pheromone-like control: controlling harmful insects by detecting pest infestations, interfering with pest mating, or attracting pests to gather. This method is increasingly attracting attention and importance due to its high efficiency, low toxicity, no residue, and low environmental risk.
[0003] Styrene compounds are locust aggregation pheromones extracted from locusts. They are exclusively released by gregarious locusts, and can be triggered by the aggregation of even just 4-5 isolated locusts. After release, both gregarious and isolated female or male locusts are strongly attracted to styrene, causing them to shift from a solitary to a gregarious lifestyle, leading to large-scale aggregation and outbreaks of locust plagues. While using styrene as a locust pheromone for attracting and killing locusts can be effective, its effect is short-lived and weak due to its reversible non-covalent binding to target proteins. However, by applying the principle of targeted covalent inhibitors (TCIs), existing natural locust styrene aggregation pheromones can be structurally modified to design and synthesize small molecule compounds with covalently bond-forming groups. These compounds can irreversibly covalently bind to specific amino acid residues of target proteins, thereby inhibiting or disrupting target protein activity and preventing them from performing their biological functions. Because their binding to target proteins is irreversible, these compounds have strong binding affinity and a long duration of action, resulting in better locust control.
[0004] Therefore, this invention designs and synthesizes a novel styrene ester-based insect covalent pheromone derivative to enhance the pheromone attraction effect, thereby preventing pests from being attracted and disturbed by natural aggregation pheromones such as styrene. The styrene ester-based covalent pheromone attracts and kills pest populations by gathering them, thereby disrupting the reproductive balance of the pest population or achieving the effect of killing them. Summary of the Invention
[0005] Technical issues: The purpose of this invention is to design a novel styrene ester-based insect covalent pheromone. This compound has stronger aggregation activity than natural aggregation pheromones such as styrene. The styrene ester-based covalent pheromone attracts and kills pest populations, thereby reducing the number and density of locust populations and the density of locust eggs. It plays a dual role of attracting and killing and "indirect killing", thus achieving the purpose of locust control.
[0006] Another objective of this invention is to provide a method for preparing a novel styrene ester-based insect covalent pheromone and its application in pest control.
[0007] Technical solution The objective of this invention is achieved through the following technical measures: A novel styrene ester-based insect covalent pheromone, wherein the pheromone derivative has the following properties: Figure 1 Compounds of the general structural formula:
[0008] In formula (1), R1 is vinyl and hydrogen; R2 is vinyl and hydrogen; R3 is hydrogen and vinyl; R4 is hydrogen, vinyl and methoxy; R5 is vinyl, hydrogen and methoxy; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propynoyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen and oxygen; n is 0, 1, 2, or 3.
[0009] In formula (2), R1 is vinyl and hydrogen; R2 is vinyl and hydrogen; R3 is hydrogen; R4 is hydrogen; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propynoyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen and oxygen; n is 0, 1, 2, or 3.
[0010] In formula (3), R1 is vinyl, hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen, methoxy; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propynoyl, alkane ester acetyl containing multiple carbons; Y is nitrogen, oxygen; n is 0, 1, 2, 3.
[0011] In formula (4), R1 is vinyl and hydrogen; R2 is vinyl and hydrogen; R3 is vinyl and hydrogen; R4 is vinyl and hydrogen; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propynoyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen and oxygen; n is 0, 1, 2, or 3.
[0012] The preferred embodiment of the novel styrene ester-based insect covalent pheromone of the present invention is as follows: 4-Vinylphenylacrylate 3-Vinylphenylacrylate (E)-2-methoxy-4-(prop-1-en-1-yl)phenylacrylate (E)-2-methoxy-4-(prop-1-en-1-yl)phenyl-2-fluoroacrylate The novel styrene ester-based insect covalent pheromones of the present invention are as follows: The compounds include: 4-Vinylphenylacrylate (E)-2-methoxy-4-(prop-1-en-1-yl)phenylacrylate 3-Vinylphenylacrylate 4-Vinyl-1,2-phenylenediacrylate 2-Fluoroacrylate-4-vinylphenyl ester (E)-2-methoxy-4-(prop-1-en-1-yl)phenyl-2-fluoroacrylate 2-Fluoroacrylate-3-vinylphenyl ester 4-Vinyl-1,2-phenylenebis(2-fluoroacrylate) The method for preparing the novel styrene ester-based insect covalent pheromone involved in this invention is as follows: the derivative is prepared by using different locust pheromone analogs hydroxyl or amino compounds as raw materials, and following reaction formulas 1-4 below, through acyl chloride reaction and EDCI and HOBt-catalyzed esterification reaction to obtain the target compound: Reaction 1 Reaction 2 Reaction 3 Reaction 4 Attached Figure Description
[0013] Figure 1 This invention provides a general formula for the synthesis of novel styrene ester-based insect covalent pheromones. Detailed implementation method:
[0014] Route 1: Preparation I: Styrene-based insect covalent pheromones Add locust pheromone alcohol, triethylamine, and dichloromethane to a round-bottom flask. o Stir at C for 5 min. Dilute acryloyl chloride with dichloromethane and slowly add it dropwise to the reaction flask. Stir at 0 °C for 2 h, then raise the temperature to 10 °C and maintain at 10 °C with stirring for 2 h. Pour the reaction solution into ice water, add HCl aqueous solution dropwise to pH=7.0, extract with dichloromethane, combine the organic phases, wash with saturated NaCl, dry with anhydrous NaSO4, filter, concentrate under reduced pressure to obtain a yellow oily crude product, purify by silica gel column chromatography (petroleum ether:ethyl acetate gradient elution = 5:1), and calculate the yield.
[0015] Example 1: 4-Vinylphenylacrylate 4-Vinylphenol (440 mg), triethylamine (1.20 g), and dichloromethane (8 mL) were added to a reaction flask and stirred at 0 s °C for 5 min. Acryloyl chloride (398 mg) was diluted with dichloromethane (8 mL) and slowly added dropwise to the reaction flask. After the addition was complete, the mixture was stirred at 0 °C for 2 h. The temperature was then raised to 10 °C and stirred for 2 h. After the reaction was complete, the mixture was poured into ice water, and hydrochloric acid solution was added dropwise until the pH reached 7.0. The mixture was extracted with dichloromethane (30 mL × 3), and the organic phases were combined, washed with saturated NaCl, dried over anhydrous NaSO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate gradient elution = 5:1) to give a pale yellow oily liquid, namely 2-(cyanomethyl)phenyl acrylate, with a yield of 47.06%. 1 H NMR (600 MHz, CDCl3) δ 7.45 –7.41 (m, 2H), 7.13 – 7.08 (m, 2H), 6.71 (dd, J = 17.5, 10.9 Hz, 1H), 6.61 (dd, J = 17.3, 1.2 Hz, 1H), 6.32 (dd, J = 17.2, 10.5 Hz, 1H), 6.02 (dd, J =10.5, 1.3 Hz, 1H), 5.72 (dd, J = 17.6, 0.8 Hz, 1H), 5.25 (dd, J = 10.9, 0.9Hz, 1H); 13 C NMR (150 MHz, CDCl3) δ 164.6, 150.3, 136.0, 135.6, 132.7, 128.0,127.3, 121.7, 114.2; HRMS (ESI) m / z calculated for C 11 H 10 O2 [M + H] + : 175.0681;found: 175.0746.
[0016] Following the preparation method of Example 1, a pale yellow oily liquid was obtained with a yield of 87.12%. 1 H NMR (600 MHz, CDCl3) δ 7.34 (t, J = 7.9 Hz, 1H), 7.28 (dt, J = 7.8, 1.4 Hz, 1H), 7.18 (t, J = 2.0 Hz, 1H), 7.03 (ddd, J= 8.0, 2.4, 1.1 Hz, 1H), 6.70 (dd, J = 17.5, 10.9Hz, 1H), 6.61 (dd, J = 17.3, 1.2 Hz, 1H), 6.33 (dd, J = 17.3, 10.5 Hz, 1H),6.02 (dd, J = 10.5, 1.2 Hz, 1H), 5.31 – 5.27 (m, 1H); 13 C NMR (150 MHz, CDCl3)δ 164.7, 151.0, 139.4, 136.1, 132.7, 129.6, 128.1, 124.0, 121.0, 119.2,115.1; HRMS (ESI) m / z Calculated for C 11 H 10 O2 [M + H] + : 175.0681; found:175.0749.
[0017] Following the preparation method of Example 1, a pale yellow oily liquid was obtained with a yield of 86.55%. 1 H NMR (600 MHz, CDCl3) δ 6.99 (d, J = 8.1 Hz, 1H), 6.94 (d, J = 1.9 Hz, 1H), 6.92 – 6.88 (m,1H), 6.63 – 6.58 (m, 1H), 6.41 – 6.32 (m, 2H), 6.20 (dq, J = 15.8, 6.6 Hz, 1H), 6.00 (ddd, J = 10.4, 5.9, 1.3 Hz, 1H), 3.83 (d, J = 2.8 Hz, 3H), 1.90 (ddd, J = 16.7, 6.9, 1.8 Hz, 3H); 13 C NMR (150 MHz, CDCl3) δ 164.3, 151.2,138.5, 137.3, 132.6, 130.6, 127.8, 126.2, 122.8, 118.5, 109.9, 56.0, 18.5; HRMS (ESI) m / z Calculated for C 13 H 14 O3 [M + H]+ : 219.0943; found: 219.1013.
[0018] Route 2: Preparation I: Styrene-based insect covalent pheromones In a round-bottom flask, 2-fluoroacrylic acid, dichloromethane, 1-hydroxybenzotriazole, and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride were added sequentially. The mixture was stirred at room temperature for 5 min, and Et3N was added dropwise. The reaction was then carried out in an ice-water bath with stirring for 30 min. 4-hydroxyphenylacetonitrile was added to the above system, and the reaction was stirred at room temperature for 4 h, with TLC monitoring during the reaction. After the reaction was completed, saturated sodium bicarbonate aqueous solution was added to quench the reaction to pH 7.0. The mixture was separated, and the aqueous phase was extracted with dichloromethane (15 mL × 3). The organic phases were combined, washed with saturated NaCl, dried over anhydrous NaSO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (petroleum ether:ethyl acetate gradient elution = 3:1) to give a pale yellow oily compound. The yield was calculated.
[0019] Example 4: (E)-2-methoxy-4-(prop-1-en-1-yl)phenyl-2-fluoroacrylate In a 250 mL round-bottom flask, 2-fluoroacrylic acid (2.90 g), dichloromethane (50 mL), 1-hydroxybenzotriazole (5.20 g), and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.90 g) were added sequentially. The mixture was stirred at room temperature for 5 min, and Et3N (6.40 g) was slowly added dropwise. The reaction was then carried out in an ice-water bath with stirring for 30 min. 3-hydroxybenzonitrile (5.00 g) was added to the mixture, and the reaction was allowed to proceed at room temperature for 4 h. The reaction was monitored by TLC during the process. After the reaction was complete, saturated sodium bicarbonate aqueous solution was added to bring the pH to 7.0. The mixture was separated, and the aqueous phase was extracted with dichloromethane (100 mL × 3). The organic phases were combined, washed with saturated NaCl, dried over anhydrous NaSO4, filtered, and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate gradient elution = 3:1) to give 3.00 g of a pale yellow oily compound, namely (E)-2-methoxy-4-(prop-1-en-1-yl)phenyl-2-fluoroacrylate, with a yield of 40.76%. 1H NMR (600 MHz, CDCl3) δ 7.01 (d, J = 8.0 Hz, 1H), 6.97 – 6.89(m, 2H), 6.37 (d, J = 15.8 Hz, 1H), 6.21 (dq, J = 13.5, 6.5 Hz, 1H), 5.91 (d,J = 43.2 Hz, 1H), 5.50 (d, J = 13.0 Hz, 1H), 3.83 (s, 3H), 1.89 (d, J = 6.7Hz, 3H); 13 C NMR (150 MHz, CDCl3) δ 158.7, 158.4, 153.8, 152.0, 150.9, 137.8,137.8, 130.4, 126.7, 122.5, 118.5, 109.9, 104.4, 104.3, 56.0, 18.6; HRMS(ESI) m / z calculated for C 12 H 11 FO3[M + H] + : 223.0692; found: 223.0617.
Claims
1. A novel styrene ester-based insect covalent pheromone, wherein the styrene ester-based covalent pheromone comprises compounds having the following general structural formula: in, In formula (1), R1 is vinyl and hydrogen; R2 is vinyl and hydrogen; R3 is hydrogen and vinyl; R4 is hydrogen, vinyl and methoxy; R5 is vinyl, hydrogen and methoxy; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroallyl, propynoyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen and oxygen; n is 0, 1, 2, or 3. In formula (2), R1 is vinyl and hydrogen; R2 is vinyl and hydrogen; R3 is hydrogen; R4 is hydrogen; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propynoyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen and oxygen; n is 0, 1, 2, or 3. In formula (3), R1 is vinyl, hydrogen; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroallyl, propargyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen, oxygen; n is 0, 1, 2, or 3. In formula (4), R1 is vinyl and hydrogen; R2 is vinyl and hydrogen; R3 is vinyl and hydrogen; R4 is vinyl and hydrogen; RC=O is allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propynoyl, or acetyl alkane ester containing multiple carbons; Y is nitrogen and oxygen; n is 0, 1, 2, or 3.
2. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In compounds of general formula (1), R1 is vinyl; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; R5 is hydrogen; RC=O represents allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propargyl, and acetyl groups of alkane esters containing multiple carbon atoms; Y represents nitrogen and oxygen; n represents 0, 1, 2, and 3.
3. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In compounds of general formula (1), R1 is hydrogen; R2 is hydrogen; R3 is vinyl; R4 is hydrogen; R5 is hydrogen; RC=O represents allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propargyl, and acetyl groups of alkane esters containing multiple carbon atoms; Y represents nitrogen and oxygen; n represents 0, 1, 2, and 3.
4. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In compounds of general formula (1), R1 is hydrogen; R2 is vinyl; R3 is hydrogen; R4 is a methoxy group; R5 is hydrogen; RC=O represents allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propargyl, and acetyl groups of alkane esters containing multiple carbon atoms; Y represents nitrogen and oxygen; n represents 0, 1, 2, and 3.
5. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In compounds of general formula (2), R1 is vinyl; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; RC=O represents allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propargyl, and acetyl groups of alkane esters containing multiple carbon atoms; Y represents nitrogen and oxygen; n represents 0, 1, 2, and 3.
6. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In compounds of general formula (3), R1 is vinyl; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; RC=O represents allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propargyl, and acetyl groups of alkane esters containing multiple carbon atoms; Y represents nitrogen and oxygen; n represents 0, 1, 2, and 3.
7. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In compounds of general formula (4), R1 is vinyl; R2 is hydrogen; R3 is hydrogen; R4 is hydrogen; RC=O represents allyl, 2,5-dioxo-2,5-dihydro-pyrrole-1-oxoformyl, 2-fluoroacetyl, 2-chloroacetyl, 2-bromoacetyl, 2-iodoacetyl, formyl, acetyl, 2-fluoroalyl, propargyl, and acetyl groups of alkane esters containing multiple carbon atoms; Y represents nitrogen and oxygen; n represents 0, 1, 2, and 3.
8. The styrene ester-based insect covalent pheromone according to claim 1, characterized in that... In the compounds of the general formula shown in Figure 1, the compounds are selected from: 4-Vinylphenylacrylate (E)-2-methoxy-4-(prop-1-en-1-yl)phenylacrylate 3-Vinylphenylacrylate 4-Vinyl-1,2-phenylenediacrylate 2-Fluoroacrylate-4-vinylphenyl ester (E)-2-methoxy-4-(prop-1-en-1-yl)phenyl-2-fluoroacrylate 2-Fluoroacrylate-3-vinylphenyl ester 4-Vinyl-1,2-phenylenebis(2-fluoroacrylate) 9. The application of the compound according to any one of claims 1 to 4 in pest control.
10. The application of the compound according to claim 5 in locust control.
11. The method for preparing styrene ester-based insect covalent pheromones according to claim 1, wherein the preparation method of the styrene ester-based covalent pheromone compound involved in the present invention is as follows: Method 1: the derivative is obtained by reacting hydroxyl or amino compounds of pheromone styrene and its analogues with different acyl chlorides according to the following reaction formulas 1 and 3; Method 2: the derivative is obtained by reacting hydroxyl or amino compounds of pheromone styrene and its analogues with different acids under the catalysis of EDCI and HOBt according to the following reaction formulas 2 and 4. Reaction 1 Reaction 2 Reaction 3 Reaction 4 12. The method for preparing styrene ester insect covalent pheromones according to claim 7, characterized in that... Hydroxyl or amino compounds are used as raw materials and reacted with acyl chlorides in a certain proportion. After the reaction, the reaction is quenched and treated to obtain a crude product. The crude product is then refined to obtain the final product. The equivalent ratio of the hydroxyl or amino compound to the acyl chloride is between 1:0.5 and 3.0; The set reaction temperature is between -10℃ and 30℃; The set time is between 1 and 15 hours; The quenching agent used for quenching is an inorganic acid; The reaction solvent, post-treatment solvent, and refining solvent are aprotic solvents.
13. The second method for preparing styrene ester insect covalent pheromones according to claim 7, characterized in that... Using hydroxyl or amino compounds as raw materials, esterification reaction is carried out with substituted acids under the action of a catalyst. After the reaction is completed, the reaction is quenched and post-processed to obtain crude product. The crude product is then purified to obtain the final product. The equivalence ratio of the various hydroxyl or amino compounds to the acids is between 1:0.5 and 5.0; The reaction temperature is between -10℃ and 50℃; The set time is between 1 and 48 hours; The quenching agent used for quenching is an inorganic alkali; The reaction solvent, post-treatment solvent, and refining solvent are aprotic solvents.
14. As described in claim 8, characterized in that The equivalence ratio of various hydroxyl or amino compounds to the corresponding acyl chloride is preferably between 1:1.0 and 1.5; the reaction temperature is preferably between 5°C and 10°C; the preferred reaction time is between 3 and 8 hours; the inorganic acid used for quenching is at least one of hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and trifluoroacetic acid, preferably dilute hydrochloric acid; the aprotic solvent is at least one of dichloromethane, ethyl acetate, petroleum ether, dioxane, chloroform, carbon tetrachloride, acetone, and saturated alkanes with 6-12 carbon atoms, preferably dichloromethane.
15. As described in claim 9, characterized in that The equivalence ratio of various hydroxyl or amino compounds to the corresponding acids is preferably between 1:1.0 and 2.0; the reaction temperature is preferably between 0°C and 30°C; the reaction time is preferably between 1 and 10 hours; the inorganic base used for quenching is at least one of potassium hydroxide, sodium hydroxide, sodium bicarbonate, potassium bicarbonate, and sodium carbonate, preferably sodium bicarbonate or potassium bicarbonate; the aprotic solvent is at least one of dichloromethane, ethyl acetate, petroleum ether, dioxane, carbon tetrachloride, acetone, and saturated alkanes with 6-12 carbon atoms, preferably dioxane.