Synthesis method of hexadecatrienol acetate compound and application of hexadecatrienol acetate compound as conopomorpha sinensis sex pheromone attractant

Abstract

The invention discloses a synthesis method of a hexadecatrienol acetate compound and application of the hexadecatrienol acetate compound as a conopomorpha sinensis sex pheromone attractant. By adopting a convergent synthesis strategy, two key pheromone compounds, namely 4-trans, 6-cis, 10-cis-hexadecatrienol acetate and 4-trans, 6-cis, 10-cis-hexadecatrienol acetate, are successfully prepared, so that not only is the synthesis efficiency remarkably improved, but also the characteristics of greenness and cleanness are achieved; the invention also provides an application of the hexadecatrienol acetate compound as a sex pheromone attractant for conopomorpha sinensis, and the hexadecatrienol acetate compound can be effectively used for monitoring and green prevention and control of conopomorpha sinensis, so that the use of chemical pesticides is reduced, and the quality safety of fruits and the sustainable development of the ecological environment are guaranteed.

Description

Technical Field

[0001] This invention relates to the field of agricultural pest and disease control technology, and in particular to a method for synthesizing a hexadecanetrienol acetate compound and its application as a sex pheromone attractant for litchi fruit borer. Background Technology

[0002] The litchi industry occupies an important position in the agricultural economy. With the optimization of litchi varieties and the advancement of large-scale planting, yield and quality have steadily improved. However, the problem of pest and disease control has not been completely solved, becoming a key factor restricting the high-quality development of the industry. Among them, the litchi fruit borer is one of the most serious pests in litchi producing areas. It bores into the tender leaves, flower spikes, and fruits of litchi trees, causing leaves to wither, flower spikes to die, and fruits to rot, directly affecting the yield and commercial value of litchis and causing significant economic losses to growers.

[0003] Currently, the control of litchi fruit borer still relies on traditional methods, which have many drawbacks: On the one hand, biological control is limited by factors such as the number of natural enemies and environmental conditions, resulting in unstable control effects and making it difficult to meet the control needs of large-scale planting; on the other hand, chemical pesticide control is currently the most widely used method, but long-term overuse of chemical pesticides not only leads to the development of pesticide resistance in litchi fruit borers, but also causes excessive pesticide residues in fruit, threatening food safety, damaging the ecological environment, and affecting the sustainable development of agriculture. Therefore, developing safe, efficient, and environmentally friendly green control technologies for litchi fruit borers has become an urgent need for the development of the litchi industry.

[0004] Insect pheromone control technology has become a core direction of green pest control systems due to its outstanding advantages such as being economical, effective, environmentally friendly, not harming natural enemies, and leaving no pesticide residues. In recent years, research on pheromones targeting the litchi fruit borer has made some progress, achieving results in areas such as host volatile matter screening, sex pheromone component identification, and antennal electrophysiological detection. However, existing pheromone compounds face several technical bottlenecks: complex biosynthetic processes and cumbersome reaction steps lead to low production efficiency; some synthetic routes rely on heavy metal oxidants, easily causing environmental pollution and contradicting the concept of green production; simultaneously, pheromone compounds suffer from unclear targets and insufficient formulation optimization, resulting in unstable attraction activity and hindering large-scale application in the field.

[0005] In summary, existing technologies for controlling litchi fruit borers have significant shortcomings, and current research on pheromones has not yet resolved the core contradiction between synthetic processes and practical applications. Therefore, developing a simple, environmentally friendly, and efficient method for synthesizing litchi fruit borer sex pheromone compounds is of great significance for promoting breakthroughs in green control technologies for litchi fruit borers and ensuring the high-quality and sustainable development of the litchi industry. Summary of the Invention

[0006] The purpose of this invention is to provide a method for synthesizing hexadecanetrienol acetate compounds and their application as sex pheromone attractants for litchi fruit borers, in order to solve the problems existing in the prior art.

[0007] To achieve the above objectives, the present invention provides the following solution: This invention provides a method for synthesizing hexadectrienol acetate compounds, wherein the hexadectrienol acetate compounds are 4-trans,6-cis,10-cis-hexadectrienol acetate or 4-trans,6-trans,10-cis-hexadectrienol acetate. The structural formula of the 4-trans,6-cis,10-cis-hexadecanetrienol acetate is: ; The structural formula of the 4-trans, 6-trans, 10-cis-hexadecanetrienol acetate is: ; The synthesis method includes the following steps: Preparation of bromine-containing unsaturated alcohols: (1) Using compound 1 as the reactant, acetylene gas was introduced into a mixed solvent system containing bromide and palladium catalyst to carry out an addition reaction, yielding a bromine-substituted unsaturated intermediate, namely compound 2; (2) The compound 2 is reduced to obtain a bromine-containing unsaturated alcohol, namely compound 3; ; Furthermore, in preparing the bromine-containing unsaturated alcohol, sodium borohydride is used for the reduction reaction; the reaction temperature is 0°C and the time is 5 hours.

[0008] Preparation of unsaturated compounds containing alkyne groups: (1) Using compound 4 as a raw material, an unsaturated aldehyde intermediate, namely compound 5, is obtained through an oxidation reaction; (2) The compound 5 was mixed with dimethyl (1-diazo-2-oxopropyl)phosphonate and reacted in the presence of potassium carbonate as a base to obtain an unsaturated compound containing an alkyne group, namely compound 6. ; Furthermore, in preparing the alkyne-containing unsaturated compound, compound 5 is prepared by an oxidation reaction using a mixed system of FeCl3 and hydrogen peroxide.

[0009] Preparation of alkynol intermediates: Compound 6 and compound 3 were reacted in a system of palladium catalyst, copper salt catalyst and amine solvent to give an alkynol intermediate, namely compound 7. ; When the hexadectrienol acetate compound is a 4-trans, 6-cis, 10-cis-hexadectrienol acetate: (1) Compound 7 was hydrogenated in the presence of a Lindlar catalyst to obtain compound 8; (2) The compound 8 was subjected to an acylation reaction to obtain the compound 9, namely 4-trans,6-cis,10-cis-hexadecanetrienol acetate; ; Furthermore, the hydrogenation reaction is carried out at a temperature of 70°C for 4 hours.

[0010] When the hexadectrienol acetate compound is a 4-trans, 6-trans, or 10-cis-hexadectrienol acetate: (1) The compound 7 was reduced in a sodium liquid ammonia reduction system to obtain compound 10; (2) The compound 10 was subjected to an acylation reaction to obtain the compound 11, namely 4-trans,6-trans,10-cis-hexadecanetrienol acetate; .

[0011] Furthermore, the reduction of compound 7 in the sodium liquid ammonia reduction system is carried out at a temperature of 0°C.

[0012] This invention employs a convergent synthesis strategy, with the longest linear step controlled to 6-7 steps, resulting in high synthesis efficiency.

[0013] The present invention also provides the application of hexadectrienol acetate compounds as sex pheromone attractants for litchi fruit borers, wherein the hexadectrienol acetate compounds are one or two of 4-trans,6-cis,10-cis-hexadectrienol acetate and 4-trans,6-trans,10-cis-hexadectrienol acetate.

[0014] Furthermore, the litchi fruit borer sex pheromone attractant is used to attract male adult litchi fruit borers.

[0015] Furthermore, in the hexadectrienol acetate, the mass ratio of 4-trans,6-cis,10-hexadectrienol acetate to 4-trans,6-trans,10-hexadectrienol acetate is (1-9):(9-1).

[0016] Furthermore, in the hexadectrienol acetate, the mass ratio of 4-trans,6-cis,10-hexadectrienol acetate to 4-trans,6-trans,10-hexadectrienol acetate is (3-7):(7-3).

[0017] The present invention discloses the following technical effects: This invention provides an efficient method for synthesizing hexadectrienol acetate compounds, successfully preparing two key pheromone compounds: 4-trans,6-cis,10-cis-hexadectrienol acetate and 4-trans,6-trans,10-cis-hexadectrienol acetate. This invention employs a convergent synthesis strategy, significantly improving synthesis efficiency and scalability; simultaneously, by abandoning the chromium-containing oxidant PCC used in traditional routes and instead employing an environmentally friendly oxidation system, green and clean production is achieved.

[0018] This invention has found that compounds 4-trans,6-cis,10-cis-hexadecanetrienol acetate and 4-trans,6-trans,10-cis-hexadecanetrienol acetate have significant olfactory sensitivity and strong attraction activity against adult male litchi fruit borers, and can be effectively used for the monitoring and green control of this pest.

[0019] This invention not only solves the problem that existing pheromone components are difficult to promote and apply due to their complex synthesis, high cost, and poor stability, but also provides the litchi industry with a safe, environmentally friendly, and efficient means of pest and disease control, which helps to reduce the use of chemical pesticides and ensure the quality and safety of fruit products and the sustainable development of the ecological environment. Attached Figure Description

[0020] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0021] Figure 1 The attraction rates of 4-trans,6-cis,10-cis-hexadecanetrienol acetate (compound 9) and 4-trans,6-trans,10-cis-hexadecanetrienol acetate (compound 11) as a single component and mixtures of different mass ratios to litchi fruit borer are analyzed.

[0022] Figure 2 The image shows the attraction effect of the control group and the experimental group (4:6 mass ratio of 4-trans, 6-cis, 10-cis-hexadecanetrienol acetate to 4-trans, 6-trans, 10-cis-hexadecanetrienol acetate) on litchi fruit borers. Detailed Implementation

[0023] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as a limitation of the present invention, but rather as a more detailed description of certain aspects, features, and embodiments of the present invention.

[0024] It should be understood that the terminology used in this invention is merely for describing particular embodiments and is not intended to limit the invention. Furthermore, with respect to numerical ranges in this invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Any stated value or intermediate value within a stated range, as well as each smaller range between any other stated value or intermediate value within said range, is also included within the scope of this invention. The upper and lower limits of these smaller ranges may be independently included or excluded from the range.

[0025] Unless otherwise stated, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. While only preferred methods and materials have been described herein, any methods and materials similar or equivalent to those described herein may be used in the implementation or testing of this invention. All references to this specification are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this specification shall prevail.

[0026] Various modifications and variations can be made to the specific embodiments described in this specification without departing from the scope or spirit of the invention, as will be apparent to those skilled in the art. Other embodiments derived from this specification will also be readily apparent to those skilled in the art. This specification and embodiments are merely exemplary.

[0027] The terms “include,” “including,” “have,” “contain,” etc., used in this article are all open-ended terms, meaning that they include but are not limited to.

[0028] It should be noted that any aspects not described in detail in this invention are conventional practices in the field and are not the focus of this invention.

[0029] The present invention will be further described in detail below with reference to embodiments: The synthetic route for 4-trans,6-cis,10-cis-hexadectrienol acetate is as follows: .

[0030] The synthetic route for 4-trans, 6-trans, 10-cis-hexadectrienol acetate is as follows: .

[0031] Example 1: Preparation of Compound 3: (1) Preparation of compound 2: Allyl aldehyde (1 eq.) was dissolved in a mixed solution of acetic acid and water, stirred until homogeneous, and then lithium bromide (1 eq.) and palladium acetate (1.5 eq.) were added. Acetylene gas was then continuously introduced into the reaction system, and the reaction was stirred overnight at room temperature. The reaction progress was monitored by thin-layer chromatography (TLC) with PE:EA = 10:1 as the developing solvent. The completion of the reaction was confirmed by UV color development, anisaldehyde staining, and alkaline potassium permanganate staining, yielding compound 2 with a yield of 86.7%. ESI-MS m / z: calcd for: C5H8BrO + [M + H] + , 163.0; found 163.0. (2) Preparation of compound 3: Compound 2 (1 eq) was dissolved in 50 ml of dry THF. The reaction system was cooled to 0 °C and stirred. Sodium borohydride (10 eq) was slowly added, and the reaction was allowed to proceed for 5 hours. After the reaction was completed, a suitable amount of dichloromethane was added to the system for extraction. The organic phase was washed successively with saturated sodium bicarbonate and brine. After drying with anhydrous sodium sulfate, the crude product was concentrated under reduced pressure and then purified by column chromatography to obtain compound 3. Yield: 75.2%. ESI-MS m / z: calcd for: C5H 10 BrO + [M + H] + , 165.0; found 165.0. Example 2 Preparation of Compound 6 (1) Preparation of compound 5: Compound 4 (2 g, 1 eq) was dissolved in 50 ml of acetonitrile and stirred at room temperature to disperse it evenly. Then, FeCl3 (207 mg, 0.1 eq) and 30% H2O2 (6.5 ml, 5 eq) were added sequentially, and the reaction was carried out for 4 h. Post-treatment: The reaction was quenched by adding saturated sodium thiosulfate, and the mixture was extracted by adding an appropriate amount of dichloromethane. The mixture was washed with saturated sodium bicarbonate, washed with brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product. The crude product was then purified by column chromatography to obtain compound 5 (1.6 g), yield: 81.2%. (Z)-dec-4-enal . 1 H NMR (500 MHz, CDCl3) δ 9.76 (t, J = 1.5 Hz, 1H), 5.45 – 5.38 (m,1H), 5.35 – 5.27 (m, 1H), 2.49 – 2.43 (m, 2H), 2.39 – 2.31 (m, 2H), 2.05 –1.99 (m, 2H), 1.35 – 1.24 (m, 6H), 0.87 (t, J= 6.9 Hz, 3H). ESI-MS m / z: calcdfor: C 10 H 19 O + [M + H] + , 155.1; found 155.1. (2) Preparation of compound 6: Compound 5 (1.6 g, 1 eq) was dissolved in 20 ml of methanol, then potassium carbonate (2 eq) was added and stirred until homogeneous. Then dimethyl (1-diazo-2-oxopropyl)phosphonate (1.3 eq) was added and the mixture was stirred at room temperature for 2 h. After the reaction was completed, water was added to the system to quench the reaction. After stirring, the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude product, and then purified by column chromatography to obtain compound 6 (1.1 g), yield: 62.8%. (Z)-undec-5-en-1-yne . 1 H NMR (500 MHz, CDCl3) δ 5.50 – 5.37 (m, 2H), 2.30 –2.25 (m, 2H), 2.24 – 2.20 (m, 2H), 2.04 (q, J = 7.0 Hz, 2H), 1.94 (t, J = 2.5 Hz,1H), 1.36 – 1.26 (m, 6H), 0.88 (t, J = 7.0 Hz, 3H). ESI-MS m / z: calcd for:C 11 H 19 + [M + H] + , 151.1; found 151.1. Example 3 Preparation of Compound 7 Compound 6 (150 mg, 1 eq) and compound 3 (1 eq) were added to 3 mL of diethylamine and stirred until homogeneous under nitrogen protection. Then, tetraphenylphosphine palladium (0.1 eq) and cuprous iodide (0.1 eq) were added, and the mixture was stirred overnight at room temperature under nitrogen protection. After the reaction was completed, the crude product was concentrated under reduced pressure and then purified by column chromatography to give compound 7 (170 mg), yield: 72.6%. (4E,10Z)-hexadeca-4,10-dien-6-yn-1-ol . 1 H NMR (400 MHz, CDCl3) δ 6.09 –5.98 (m, 1H), 5.55 – 5.35 (m, 3H), 3.64 (t, J= 6.5 Hz, 2H), 2.35 – 2.22 (m,4H), 2.21 – 2.13 (m, 2H), 2.07 – 1.99 (m, 2H), 1.69 – 1.61 (m, 2H), 1.36 –1.26 (m, 6H), 0.88 (t, J = 6.8 Hz, 3H), OH (not observed). ESI-MS m / z: calcdfor: C 16 H 27 O + [M + H] + , 235.2; found 235.2. Example 4 Preparation of 4-trans,6-cis,10-cis-hexadecanetrienol acetate (1) Preparation of compound 8: Compound 7 (50 mg, 1 eq) was added to a mixed solvent of 0.2 mL pyridine and 1 mL ethanol. After stirring evenly, 20 mg of Lindlar catalyst was added, and the mixture was heated to 70 °C for 4 h while maintaining hydrogen pressure. After the reaction was completed, an appropriate amount of ethyl acetate and 1N hydrochloric acid were added to the reaction system, and the mixture was extracted by separation. The organic phase was then subjected to 1N hydrochloric acid, The product was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the crude product was purified by column chromatography to give compound 8 (38 mg), yield: 75.3%. (4E,6Z,10Z)-hexadeca-4,6,10-trien- 1-ol . 1 H NMR (400 MHz, CDCl3) δ 6.39 – 6.28 (m, 1H), 6.00 – 5.92 (m, 1H), 5.67(dt, J = 14.6, 7.0 Hz, 1H), 5.44 – 5.27 (m, 3H), 3.68 – 3.60 (m, 2H), 2.25 –2.10 (m, 4H), 2.08 – 1.96 (m, 4H), 1.72 – 1.62 (m, 2H), 1.32 – 1.22 (m, 6H),0.88 (t, J = 6.8 Hz, 3H), OH (not observed). ESI-MS m / z: calcd for: C 16 H 29 O + [M +H] + , 237.2; found 237.2. (2) Preparation of 4-trans, 6-trans, 10-cis-hexadecanetrienol acetate: Compound 8 (20 mg, 1 eq) and DMAP (3 eq) were dissolved in 1 mL of dichloromethane by stirring. Then, acetic anhydride (2 eq) was added, and the mixture was stirred at room temperature for 1 h. After the reaction was completed, water was added to quench the reaction, and the reaction solution was extracted with dichloromethane. The organic phase was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography to give compound 9 (18 mg), yield: 76.5%. (4E,6Z,10Z)-hexadeca-4,6,10-trien-1-yl acetate . 1 H NMR (500MHz, CDCl3) δ 6.38 – 6.27 (m, 1H), 5.95 (t, J = 11.0 Hz, 1H), 5.68 – 5.59 (m,1H), 5.43 – 5.29 (m, 3H), 4.07 (t, J = 6.5 Hz, 2H), 2.25 – 1.96 (m, 11H), 1.78 – 1.69 (m, 2H), 1.35 – 1.25 (m, 6H), 0.88 (t, J = 7.0 Hz, 3H). ESI-MS m / z:calcd for C 18 H 31 O2 + [M + H] + , 279.2; found 279.2. Example 5 Preparation of 4-trans, 6-trans, 10-cis-hexadecanetrienol acetate (1) Preparation of compound 10: Compound 7 (50 mg, 1 eq) was dissolved in 2 ml of methanol and stirred until homogeneous. The reaction vessel was placed in an ice bath environment, and 1 eq. of sodium ammonia solution was added. The reaction was carried out under ice bath conditions for 2 h. After the reaction was completed, an appropriate amount of ice water and ethyl acetate were added, and the mixture was extracted by separation. The organic phase was washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine. After drying with anhydrous sodium sulfate, the crude product was concentrated under reduced pressure. Then, compound 10 was purified by column chromatography with a yield of 30.5%. (4E,6E,10Z)-hexadeca-4,6,10-trien-1-ol . 1 H NMR (500 MHz, CDCl3) δ 6.07 –5.98 (m, 2H), 5.63 – 5.53 (m, 2H), 5.45 – 5.36 (m, 2H), 3.61 (t, J= 6.5 Hz,2H), 2.23 – 2.19 (m, 2H), 2.16 – 2.11 (m, 2H), 2.05 – 2.01 (m, 2H), 1.70 –1.64 (m, 2H), 1.42 – 1.18 (m, 6H), 0.90 (t, J = 7.0 Hz, 3H), OH (not observed).ESI-MS m / z: calcd for: C 16 H 29 O + [M + H] + , 237.2; found 237.2. (2) Preparation of 4-trans, 6-trans, 10-cis-hexadecanetrienol acetate: Compound 10 (20 mg, 1 eq) and DMAP (3 eq) were added to 1 ml of dichloromethane and stirred to dissolve. Acetic anhydride (2 eq) was then added and stirred at room temperature for 1 h. After the reaction was completed, the reaction was quenched with water, extracted with dichloromethane, and the organic phase was washed with brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography to obtain compound 11 (18 mg), yield: 76.5%. 1 H NMR (500 MHz, CDCl3) δ 6.07 – 5.98 (m, 2H), 5.63 – 5.53 (m, 2H), 5.45 – 5.36 (m, 2H), 3.61(t, J = 6.5 Hz, 2H), 2.23 – 2.10 (m, 7H), 2.05 – 2.01 (m, 2H), 1.70 – 1.64 (m,2H), 1.42 – 1.18 (m, 6H), 0.90 (t, J = 7.0 Hz, 3H), ESI-MS m / z: calcd forC 18 H 31 O2 + [M + H] + , 279.2; found 279.2. Example 1: Validation of the effect of the compound on the behavior of the litchi fruit borer. Unmated male adults of the litchi fruit borer were selected as test insects. The experiment included a control group and an experimental group, with 30 male adults in each group. Paraffin oil was used as the control group. The test samples in the experimental group included single components of the above-prepared 4-trans,6-cis,10-hexadecanetrienol acetate (compound 9) and 4-trans,6-trans,10-hexadecanetrienol acetate (compound 11), as well as mixed samples prepared by different mass ratios of the two compounds.

[0032] The experiment was conducted in an area of ​​15m² 2 The experiment was conducted in an indoor environment to simulate the ecological conditions of a litchi orchard, and to verify olfactory behavior selection. Each experiment was repeated three times to ensure data reliability. After the experiment, the number of male adults attracted in each group was counted, the attraction rate was calculated, and comparative analysis was performed.

[0033] Figure 1 The attraction rates of 4-trans,6-cis,10-cis-hexadecanetrienol acetate (compound 9) and 4-trans,6-trans,10-cis-hexadecanetrienol acetate (compound 11) as a single component and mixtures of different mass ratios to litchi fruit borer are analyzed.

[0034] The test results showed that the attraction rate of the control group to male adult litchi fruit borers was only 8.89%, while different ratios of compounds in the experimental group showed different attraction activities. Among them, the attraction rate of compound 9:compound 11 in a mass ratio of 4:6 to male adult litchi fruit borers was as high as 73.34%, which was significantly higher than that of the control group. Secondly, the range of ratios with attraction rates above 50% was 3:7 to 7:3.

[0035] Figure 2 The image shows the attraction effect of the control group and the experimental group (4:6 mass ratio of 4-trans, 6-cis, 10-cis-hexadecanetrienol acetate to 4-trans, 6-trans, 10-cis-hexadecanetrienol acetate) on litchi fruit borers.

[0036] The results showed that the hexadecyltrienol acetate compound could effectively attract male adult litchi fruit borers, and had core application value as a sex pheromone attractant for litchi fruit borers.

[0037] The embodiments described above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Various modifications and improvements made by those skilled in the art to the technical solutions of the present invention without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.

Claims

1. A method for synthesizing hexadectrienol acetate compounds, characterized in that, The hexadectrienol acetate compounds are 4-trans, 6-cis, 10-cis-hexadectrienol acetate or 4-trans, 6-trans, 10-cis-hexadectrienol acetate; The synthesis method includes the following steps: Preparation of bromine-containing unsaturated alcohols: (1) Using compound 1 as the reactant, acetylene gas was introduced into a mixed solvent system containing bromide and palladium catalyst to carry out an addition reaction, yielding a bromine-substituted unsaturated intermediate, namely compound 2; (2) The compound 2 is reduced to obtain a bromine-containing unsaturated alcohol, namely compound 3; ； Preparation of unsaturated compounds containing alkyne groups: (1) Using compound 4 as a raw material, an unsaturated aldehyde intermediate, namely compound 5, is obtained through an oxidation reaction; (2) The compound 5 was mixed with dimethyl (1-diazo-2-oxopropyl)phosphonate and reacted in the presence of potassium carbonate to obtain an unsaturated compound containing an alkyne group, namely compound 6. ； Preparation of alkynol intermediates: Compound 6 and compound 3 were reacted in a system of palladium catalyst, copper salt catalyst and amine solvent to give an alkynol intermediate, namely compound 7. ； When the hexadectrienol acetate compound is a 4-trans, 6-cis, 10-cis-hexadectrienol acetate: (1) Compound 7 was hydrogenated in the presence of a Lindlar catalyst to obtain compound 8; (2) The compound 8 was subjected to an acylation reaction to obtain compound 9, namely 4-trans,6-cis,10-cis-hexadecanetrienol acetate; ； When the hexadectrienol acetate compound is a 4-trans, 6-trans, or 10-cis-hexadectrienol acetate: (1) The compound 7 was reduced in a sodium liquid ammonia reduction system to obtain compound 10; (2) The compound 10 was subjected to an acylation reaction to obtain compound 11, namely 4-trans,6-trans,10-cis-hexadecanetrienol acetate; 。 2. The preparation method according to claim 1, characterized in that, In preparing the alkynyl-containing unsaturated compound, an oxidation reaction is carried out using a mixture of FeCl3 and hydrogen peroxide.

3. The preparation method according to claim 1, characterized in that, The hydrogenation reaction was carried out at a temperature of 70°C for 4 hours.

4. The preparation method according to claim 1, characterized in that, The reduction of compound 7 in the sodium liquid ammonia reduction system was carried out at a temperature of 0°C.

5. The application of hexadecyltrienol acetate compounds as sex pheromone attractants for litchi fruit borers, characterized in that, The hexadectrienol acetate compounds are one or two of 4-trans, 6-cis, 10-cis-hexadectrienol acetate and 4-trans, 6-trans, 10-cis-hexadectrienol acetate.

6. The application according to claim 5, characterized in that, The litchi fruit borer sex pheromone attractant is used to attract male adult litchi fruit borers.

7. The application according to claim 5, characterized in that, The mass ratio of 4-trans,6-cis,10-cis-hexadectrienol acetate to 4-trans,6-trans,10-cis-hexadectrienol acetate is (1-9):(9-1).

8. The application according to claim 7, characterized in that, The mass ratio of 4-trans, 6-cis, 10-cis-hexadectrienol acetate to 4-trans, 6-trans, 10-cis-hexadectrienol acetate is (3-7): (7-3).

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