阅读说明：本技术 茶尺蠖和灰茶尺蠖高效复配性诱芯 (Efficient compound lure of tea geometrid and gray tea geometrid ) 是由 陈新 陈珂 张雪媛 张成芳 毕建龙 金燕强 单明伟 赵帅 钱明成 于 2021-08-17 设计创作，主要内容包括：本发明属于茶园害虫茶尺蠖和灰茶尺蠖生物防治领域,具体涉及一种茶尺蠖和灰茶尺蠖高效复配性诱芯。将(3Z,6Z,9Z)-十八碳三烯与两种不同构型的(3Z,9Z)-6,7-环氧-十八碳二烯和(3Z,6Z)-9,10-环氧-十八碳二烯复配,得到一种高效复配性诱芯,该复配性诱芯对茶尺蠖和灰茶尺蠖具有显著提高的诱捕效果。(The invention belongs to the field of biological control of tea garden pest loopers and gray tea loopers, and particularly relates to an efficient compound lure of tea loopers and gray tea loopers. The (3Z,6Z,9Z) -octadecatriene is compounded with two (3Z,9Z) -6, 7-epoxy-octadecadienol and (3Z,6Z) -9, 10-epoxy-octadecadienol with different configurations to obtain the high-efficiency compounded lure, and the compounded lure has obviously improved trapping effect on tea geometrid and ash geometrid.)

1. An efficient compound lure of tea geometrid and gray tea geometrid is characterized in that effective components of the compound lure comprise two octadecadienone epoxides and (3Z,6Z,9Z) -octadecatriene.

2. The tea geometrid and gray tea geometrid highly effective compounded lure according to claim 1, wherein the octadecadienoic epoxide is any two of (6Z,9Z) -3, 4-epoxy-octadecadienol, (3Z,9Z) -6, 7-epoxy-octadecadienol or (3Z,6Z) -9, 10-epoxy-octadecadienol.

3. The tea geometrid and gray tea geometrid high efficiency compounded lure according to claim 2, wherein the (6Z,9Z) -3, 4-epoxy-octadecadienol is (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol or (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol.

4. The tea geometrid and gray tea geometrid high efficiency compounded lure according to claim 2, wherein the (3Z,9Z) -6, 7-epoxy-octadecadienol is (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol or (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol.

5. The tea geometrid and gray tea geometrid high efficiency compounded lure according to claim 2, wherein the (3Z,6Z) -9, 10-epoxy-octadecadienol is (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol or (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol.

6. The tea geometrid and gray tea geometrid highly potent compounded lure according to claim 1, wherein the two octadecadieneoxide compounds are (3Z,9Z) -6, 7-epoxy-octadecadienol and (3Z,6Z) -9, 10-epoxy-octadecadienol.

7. The tea geometrid and gray tea geometrid highly effective compounded lure according to claim 6, wherein the two octadecadieneoxide compounds are (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol.

8. The efficient compound lure according to claim 7, wherein the weight ratio of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol to (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol is 9:1-1: 9.

9. The tea geometrid and gray tea geometrid high-efficiency compounded lure according to claim 2, wherein the synthetic method of (3Z,6Z) -9, 10-epoxy-octadecadiene comprises the following steps:

(1) synthesizing (2S,3S) -1,2, 3-undecanetriol;

(2) synthesizing (2S,3S) -1, 2-epoxy-3-p-toluenesulfonate-undecane;

(3) synthesizing (9S,10R) -9, 10-epoxy-octadecane-3, 6-diyne;

(4) synthesizing (3Z,6Z) -9, 10-epoxy-octadecadienol.

10. The application of the tea geometrid and ash tea geometrid high-efficiency compounded lure according to any one of claims 1 to 8, wherein the compounded lure is used for controlling tea geometrid and ash tea geometrid, which are pests in a tea garden.

Technical Field

The invention belongs to the technical field of tea geometrid and gray tea geometrid control, and particularly relates to an efficient compound lure of tea geometrid and gray tea geometrid.

Background

Tea geometrid, known as Ectropis obliques hypulina Wehrli, belongs to Lepidoptera, geometrid moth family, and is one of the main pests of tea trees in China. The edges of young leaves of tea geometrid which are eaten by low-age larvae are in a net-shaped semitransparent film spot, and the young leaves of tea geometrid which are eaten by high-age larvae are in a C-shaped nick. When serious, young shoots and old leaves of tea trees are eaten to form baldness, only bald branches are left, and the tea production is greatly influenced as the tea trees are burnt. The ectropis grisescens and the ectropis grisescens belong to kindred species, are extremely similar in shape, overlap in occurrence area and time, and have the same host plant. In order to better ensure pollution-free organic planting of tea, various non-toxic and environment-friendly technologies such as physical control and biological control are gradually replacing traditional pesticides.

The method for preventing and controlling the tea geometrid by utilizing the insect sex pheromone is a high-efficiency, single and environment-friendly biological prevention and control technology. There are many reports on the identification and synthesis of the sex pheromone of tea geometrid, 1994, Liutianlin et al preliminarily identified two important components of the sex pheromone of tea geometrid as (3Z,6Z,9Z) -octadecatriene and (3Z,9Z) -6, 7-epoxyoctadecadienol (Liutianlin, Li's famous name, Luo Qiang, etc.. the synthesis of several active ingredients of the sex pheromone of tea geometrid. Nankai university newspaper (Nature science edition) 1994: 82-86). In 2017, the Acronochhun topic group (J.Yu, F.Guo, Y.Q.Yang, et al.Synthesis of the antioxidant compositions of (3Z,9Z) -cis-6,7-epoxy-3, 9-octadiene, one of the major compositions of the sex phenomene of the Ectropis obliques. tetrahedron asymmetry.2017,28: 758. sylvestris 761) and the New topic group (K.Xu, S.ZHao, J.K.Xu, et al.Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S) -6,7-epoxy-3, 9-octadiene. Synth. Commun. 1847, Com.8: 2016, 7-octadiene-3, 9Z, 7S-6, 7-epoxy-7, 9-octadiene-8, 7-octadiene-3, 9Z, 7S-7, 7-octadiene-6, 7S-octadiene-6, 7-octadiene-7, 7-octadiene-6, 7-octadiene-6, 7-epoxy-octadiene-6, 7, and the like, and the epoxy-7-6-7-6-epoxy-2-6, and the synthetic method thereof, wherein the epoxy-7, and the epoxy-6, and the epoxy-7-epoxy-6 are used in the experiments, respectively, and the experiments were carried out, and the experiments, respectively, but the experiments were carried out in which were carried out in the experiments.

Disclosure of Invention

The invention aims to provide an efficient compound lure of tea geometrid and ash tea geometrid and a preparation method of a synergistic component of the compound lure.

The inventors have found that octadecadienoic epoxide is one or more regioisomers of octadecadienoic epoxide, including the 3,4-, 6, 7-and 9, 10-position epoxides. In order to optimize the trapping activity of the tea geometrid sex attractant, the structure of the octadecadienoic epoxide and the proportion of each regioisomer were deeply studied.

The effective components of the high-efficiency compound lure comprise (3Z,6Z,9Z) -octadecatriene and two octadecadiene epoxides.

The octadecadienoic epoxide is any two of (6Z,9Z) -3, 4-epoxy-octadecadienol, (3Z,9Z) -6, 7-epoxy-octadecadienol or (3Z,6Z) -9, 10-epoxy-octadecadienol.

The (6Z,9Z) -3, 4-epoxy-octadecadienol is (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol (abbreviated as (6Z,9Z-3S,4R) -epoxy-18: H) or (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol ((6Z,9Z-3R,4S) -epoxy-18: H) (formula 1).

The (3Z,9Z) -6, 7-epoxy-octadecadienol is (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol ((3Z,9Z-6S,7R) -epoxy-18: H) or (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol ((3Z,9Z-6R,7S) -epoxy-18: H). (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol is preferred.

(3Z,6Z) -9, 10-epoxy-octadecadien is (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadien ((3Z,6Z-9S,10R) -epoxy-18: H) or (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadien ((3Z,6Z-9R,10S) -epoxy-18: H), preferably (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadien.

The preferred two octadecadienoic epoxides of the invention are (3Z,9Z) -6, 7-epoxy-octadecadienol and (3Z,6Z) -9, 10-epoxy-octadecadienol.

Further preferred two octadecadieneoxides are (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol.

Wherein the weight ratio of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadiene to (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadiene is 9:1-1: 9.

Structure of six chiral epoxy isomers of octadecadiene epoxide of formula 1

Wherein, (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienoic acid ((3Z,6Z-9S,10R) -epoxy-18: H) (I) and (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienoic acid ((3Z,6Z-9R,10S) -epoxy-18: H) (II) are used as synergistic components of the high-efficiency compound lure of tea geometrid and ash geometrid, and the synthetic route is shown as formula 2.

A synthetic route to (3Z,6Z-9S,10R) -epoxy-18: H (I) and (3Z,6Z-9R,10S) -epoxy-18: H (II)

The invention has the beneficial effects that: the (3Z,6Z) -9, 10-epoxy-octadecadienoic acid has synergistic effect on trapping tea geometrid and gray tea geometrid for the first time, and the trapping effect of the (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienoic acid and the (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienoic acid after being compounded on the tea geometrid and gray tea geometrid is obviously improved.

Detailed Description

The invention will now be further illustrated by reference to specific examples, which are intended to be illustrative of the invention and are not intended to be a further limitation of the invention.

Synthesis of efficient compound core-inducing synergistic component

Example 1: synthesis of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadien (I)

Step 1: synthesis of (2S,3S) -1,2, 3-undecalatriol

AD-mix-alpha (41.2g) was dissolved in tert-butanol: water 1:1 (total 200mL), the system was cooled to 0 ℃ and methylsulfonamide (2.8g, 29mmoL) and trans-2-undecenol (5g, 29mmoL) were added and reacted for 3 days. TLC monitoring, adding NaHSO slowly at 0 deg.C₄(54g) Quenching, suction filtering, extracting the filtrate with ethyl acetate, spin-drying, and purifying by column chromatography to obtain white solid (2S,3S) -1,2, 3-undecanetriol (4.5g, yield 75%).

Step 2: synthesis of (2S,3S) -1, 2-epoxy-3-p-toluenesulfonate-undecane

(2S,3S) -1,2, 3-undecanetriol (4.4g, 21.6mmoL) was dissolved in dry tetrahydrofuran (150mL), the system was cooled to 0 ℃, NaH (2.59g, 64.8mmoL) was slowly added thereto, stirred for 30 minutes, and then Tos-Im (11.5g, 51.8mmoL) was added thereto and reacted at room temperature for 4.5 hours. Monitored by TLC, quenched with water (57.9mL) at 0 deg.C, extracted with water, ethyl acetate and water, and purified by column chromatography to give (2S,3S) -1, 2-epoxy-3-p-toluenesulfonate-undecane as a white solid (3g, 41% yield).

And step 3: synthesis of (9S,10R) -9, 10-epoxy-octadecane-3, 6-diyne

Dried tetrahydrofuran (130mL) was added with 3, 6-heptadiyne (2.34g, 25.4mmoL), -78 ℃ under nitrogen, n-butyllithium (10.3mL,25.4mmoL,2.5M in hexane) was added dropwise, reacted for 15 minutes, boron trifluoride ether (2.4g, 21.2mmoL) was added again, reacted for 10 minutes, and then (2S,3S) -1, 2-epoxy-3-p-toluenesulfonate-undecane (2.9g, 8.5mmoL) was dissolved in tetrahydrofuran (20mL) and added dropwise, and reacted at-78 ℃ for 12 hours. TLC monitoring, saturated NH addition₄Quenching with Cl (20mL), extraction with ethyl acetate, spin-drying the organic phase, addition of methanol (40mL), addition of K at 0 deg.C₂CO₃(4.64g, 33.1mmoL), methanol was dried after the reaction was completed, extracted with ethyl acetate, and the solvent was dried and purified by column chromatography to obtain (4S,5R) -4, 5-epoxy-tridec-1-yne (0.54g, yield 25%) as an oily liquid.

And 4, step 4: synthesis of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadien (I)

A100 mL round-bottom flask was charged with n-hexane (15mL), Lindlar catalyst (32mg), hydrogen replaced 3 times, and (9S,10R) -9, 10-epoxy-octadeca-3, 6-diyne (0.32g, 1.2mmoL) under hydrogen for 5 hours. TLC monitoring, silica gel filtration, ethyl acetate filter cake washing, spin drying of the filtrate, column chromatography purification to give yellow oily liquid (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol (124mg, 38% yield).¹H NMR(500MHz,CDCl₃)δ:5.27-5.54(m,4H),2.91-2.95(m,2H),2.80(t,J＝7.0Hz,2H),2.36-2.43(m,1H),2.19-2.25(m,1H),2.03-2.11(m,2H),1.47-1.54(m,2H),1.27-1.45(m,12H),0.97(t,J＝7.5Hz,3H),0.88(t,J＝6.5Hz,3H)；¹³C NMR(125MHz,CDCl₃)δ:132.5,130.9,126.7,124.3,57.2,56.6,32.0,29.6,29.7,29.4,27.9,26.8,26.4,25.8,22.8,20.7,14.4,14.2；MS(ESI):m/z 287[M+Na]⁺.

Example 2: synthesis of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadien (II)

The synthesis was carried out as in example 1, except that the catalyst was changed to AD-mix-beta in the Sharpless asymmetric dihydroxylation step.

The spectrum data of the obtained (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadiene are as follows:¹H NMR(500MHz,CDCl₃)δ:5.27-5.55(m,4H),2.91-2.96(m,2H),2.80(t,J＝7.0Hz,2H),2.38-2.43(m,1H),2.19-2.25(m,1H),2.04-2.10(m,2H),1.42-1.58(m,2H),1.25-1.37(m,12H),0.97(t,J＝7.5Hz,3H),0.88(t,J＝6.7Hz,3H)；¹³C NMR(125MHz,CDCl₃)δ:132.5,130.9,126.7,124.4,57.5,56.6,32.0,29.7,29.6,29.4,27.9,26.8,26.4,25.8,22.8,20.8,14.4,14.3；MS(ESI):m/z 282[M+NH₄]⁺.

efficient compound trapping core for trapping tea geometrid

(1) Screening of single octadecadienoic epoxide

Example 3: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene and 3.75mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadiene in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 4: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene and 3.75mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadiene in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 5: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene and 3.75mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadiene in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 6: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene and 3.75mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadiene in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 7: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene and 3.75mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadiene in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 8: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene and 3.75mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadiene in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 9: the field trapping test was conducted in the tea base of Jintanxin tea-tasting Co., Ltd, Changzhou, Jiangsu province. The lure used in the test was prepared according to the protocol described in examples 3-8, and the blank control was a lure prepared from n-hexane. The lure was used in conjunction with the traps, 3 replicates per treatment, and the number of traps was counted for 1 month. The trapping results of examples 3-8 are shown in Table 1.

TABLE 1 examples 3-8 field trapping results for tea geometrid

The results show that: the octadecadienoic epoxide with different configurations has obvious difference on the trapping effect of the tea geometrid male moth,

(3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol have a certain trapping activity, while (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol, (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol, (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol, (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol have no trapping effect.

(2) Screening of binary octadecadienoic epoxide: (3Z,9Z) -6, 7-epoxy-octadecadienol and (3Z,6Z) -9, 10-epoxy-octadecadienol

Example 10: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 0.375mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 11: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.125mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 0.625mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 12: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 2.5mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 1.25mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 13: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 1.875mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 14: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.25mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 2.5mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 15: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.625mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 3.125mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 16: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 3.375mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 17: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 0.375mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 18: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 1.875mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 19: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 3.375mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 20: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 0.375mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 21: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 1.875mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 22: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 3.375mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 23: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 0.375mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 24: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 1.875mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 25: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 3.375mg of (3Z,6Z-9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

(3) Screening of binary octadecadienoic epoxide: (3Z,9Z) -6, 7-epoxy-octadecadienol and (6Z,9Z) -3, 4-epoxy-octadecadienol combination

Example 26: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 0.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 27: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 1.875mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 28: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 3.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 29: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 0.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 30: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 1.875mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 31: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and 3.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 32: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 0.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 33: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 1.875mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 34: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 3.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 35: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 0.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 36: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 1.875mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 37: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (3Z,9Z,6R,7S) -6, 7-epoxy-octadecadienol and 3.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

(4) Screening of binary octadecadienoic epoxide: (6Z,9Z) -3, 4-epoxy-octadecadienol and (3Z,6Z) -9, 10-epoxy-octadecadienol combination

Example 38: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol and 0.375mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 39: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol and 1.875mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 40: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol and 3.375mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 41: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol and 0.375mg of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 42: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol and 1.875mg of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 43: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol and 3.375mg of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 44: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol and 0.375mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 45: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol and 1.875mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 46: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol and 3.375mg of (3Z,6Z,9S,10R) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 47: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 3.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol and 0.375mg of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 48: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 1.875mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol and 1.875mg of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 49: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 0.375mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol and 3.375mg of (3Z,6Z,9R,10S) -9, 10-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 50: the field trapping test was conducted in the tea base of Jintanxin tea-tasting Co., Ltd, Changzhou, Jiangsu province. The lure used in the test was prepared according to the protocol described in examples 3-8, and the blank control was a lure prepared from n-hexane. The lure was used in conjunction with the traps, 3 replicates per treatment, and the number of traps was counted for 1 month. The trapping results of examples 10-49 are shown in Table 2.

TABLE 2 examples 10-49 field trapping results for tea geometrid

The results show that: when the octadecadienoic epoxide is composed of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol, the effect of trapping the tea geometrid male moth is better, and the weight ratio of the two is 2:1, the effect is best.

(5) Screening of ternary octadecadienoic epoxide: (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol and (6Z,9Z) -3, 4-epoxy-octadecadienol

Example 51: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 2.5mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol, 1.25mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol and 0.19mg of (6Z,9Z,3S,4R) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 52: dissolving 1.25mg of (3Z,6Z,9Z) -octadecatriene, 2.5mg of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol, 1.25mg of (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol and 0.19mg of (6Z,9Z,3R,4S) -3, 4-epoxy-octadecadienol in n-hexane, dropwise adding the obtained solution into a slow-release carrier, and obtaining the lure after the solvent is volatilized.

Example 53: the field trapping test was conducted in the tea base of Jintanxin tea-tasting Co., Ltd, Changzhou, Jiangsu province. The test wicks were prepared according to the protocol described in examples 51-52, and the control wicks were the wicks of example 12. The lure was used in conjunction with the traps, 3 replicates per treatment, and the number of traps was counted for 1 month. The trapping results of examples 51-52 are shown in Table 3.

TABLE 3 field trapping results for tea geometrid in examples 51-52

Treatment of	Total number of traps (head)	Average number of traps (head/trap)
			Example 12	183	61
Example 51	121	40.3
			Example 52	108	36

The results show that: the effect of trapping tea geometrid is not improved when (6Z,9Z) -3, 4-epoxy-octadecadienol is added on the basis of (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol, and the effect of trapping cores is the best when (3Z,9Z,6S,7R) -6, 7-epoxy-octadecadienol and (3Z,6Z-9S,10R) -9, 10-epoxy-octadecadienol are combined.

Efficient compound trapping core for trapping tea geometrid and gray tea geometrid

Example 54: the field trapping test was conducted in the tea base of Jintanxin tea-tasting Co., Ltd, Changzhou, Jiangsu province. The wicks used in the tests were made according to the protocol described in example 12. The lure was used in conjunction with the traps, 3 replicates per treatment, and the number of traps was counted for 1 month. The trapping results of example 12 are shown in Table 4.

Table 4 example 12 field trapping results for tea geometrid and gray tea geometrid

The results show that: the high-efficiency compound lure corresponding to the embodiment 12 has good trapping effect on both the tea geometrid and the gray tea geometrid, has better effect on the gray tea geometrid, and may have a relationship with the high density of the mouths of the gray tea geometrid in a tea garden.