Compound, composition and application of compound and composition in preparation of mulberry inchworm attractant

Abstract

The invention relates to the technical field of biological medicines, and particularly discloses a compound, a composition and application of the compound and the composition in preparation of a mulberry inchworm attractant. The compound is selected from the group consisting of (6Z, 9S, 10R)-9, 10-epoxy octadecene, (3Z, 6Z, 9S, 10R)-9, 10-epoxy octadecene, (3Z, 6Z, 9S, 10R)-9, 10-epoxy octadecene, (3Z, 6Z, 9S, 10R)-9, 10-epoxy octadecene or ionone. The invention relates to an epoxy resin composition, which comprises (6Z, 9S, 10R)-9, 10-epoxy octadecane-6-alkene, (3Z, 6Z, 9S, 10R)-9, 10-epoxy octadecane-3, 6-diene and ionone. Researches show that the compound and the composition provided by the invention can cause an antennal potential reaction of male mulberry inchworm; particularly, the composition obtained by combining the compounds can improve the electroantennal potential reaction of male mulberry inchworm; therefore, the compound or the composition provided by the invention can be used as a mulberry inchworm attractant for trapping mulberry inchworms, can realize efficient trapping of mulberry inchworms, is green, environment-friendly, high in specificity, safe and efficient, and has a great development prospect.

Description

Technical Field

[0001] The present invention relates to the technical field of biomedicine, and in particular to a compound, a composition and application thereof in the preparation of a mulberry looper attractant. Background Art

[0002] The electroantennographic technique (EAG) is the most commonly used electrophysiological technique in chemical ecology. It is a fundamental test used to determine whether a substance stimulates a living insect or a part of its organ (such as its antennae). EAG is a highly useful electrophysiological method and has become essential for studying both populations and individual insect olfactory cells. EAG is also widely used to investigate the responses of herbivorous insects to their pheromone compounds. This technique is primarily used to understand the effects of different pheromone compounds on the electrophysiological characteristics of insect olfaction, enabling compound screening and identification of pheromones.

[0003] In the study of insect pheromones and plant volatiles, this technology can be used to screen active components from a series of synthetic compounds; on the other hand, the identified active components are appropriately proportioned and dosed to form different treatments, and then screened using EAG. The combination with strong activity is selected as the basis for the next indoor biotest or field test. This can greatly simplify subsequent work, and in some aspects the screening results obtained are consistent with the wind tunnel biotest results.

[0004] The mulberry looper (Hemerophila atrilineata Butler) is a major pest in the silkworm industry. It harms mulberry trees by feeding on mulberry buds and leaves, and its excrement contaminates the leaves, causing a decrease in their quality. Current methods for controlling mulberry loopers include manual capture, pesticide spraying, and natural enemy control. However, attracting looper pheromones is more environmentally friendly, efficient, and convenient than these methods, making it a mainstream control method. Therefore, developing a mulberry looper attractant has important application value. Summary of the Invention

[0005] In order to overcome at least one technical problem existing in the prior art, the present invention provides a compound, a composition and use thereof in preparing a mulberry looper attractant.

[0006] The technical solutions of the present invention are as follows:

[0007] The present invention first provides an application of a compound in the preparation of a mulberry looper attractant, wherein the compound is selected from (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene (referred to as compound 1), (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene (referred to as compound 2) or ionone.

[0008] The present invention also provides a composition comprising (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene.

[0009] Preferably, the mass ratio of (6Z,9S,10R)-9,10-epoxyoctadec-6-ene to (3Z,6Z,9S,10R)-9,10-epoxyoctadec-3,6-diene is 1-20:1-20.

[0010] Preferably, the mass ratio of (6Z,9S,10R)-9,10-epoxyoctadec-6-ene to (3Z,6Z,9S,10R)-9,10-epoxyoctadec-3,6-diene is 1-15:1-15.

[0011] Preferably, the mass ratio of (6Z,9S,10R)-9,10-epoxyoctadec-6-ene to (3Z,6Z,9S,10R)-9,10-epoxyoctadec-3,6-diene is 1:1-15.

[0012] Preferably, the mass ratio of (6Z,9S,10R)-9,10-epoxyoctadec-6-ene to (3Z,6Z,9S,10R)-9,10-epoxyoctadec-3,6-diene is 1:10.

[0013] Preferably, the composition further comprises ionone.

[0014] Preferably, the mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene, (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene and ionone in the composition is 1:5-15:1-15.

[0015] Preferably, the mass ratio of (6Z,9S,10R)-9,10-epoxyoctadec-6-ene, (3Z,6Z,9S,10R)-9,10-epoxyoctadec-3,6-diene and ionone in the composition is 1:10:7.

[0016] The present invention also provides an application of the composition in preparing an attractant for loblolly moths.

[0017] Beneficial effects: Studies have shown that the compounds and compositions described in the present invention can induce the antennal potential response of male mulberry loopers; in particular, the composition obtained by combining (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene or further combining them with ionone can improve the antennal potential response of male mulberry loopers; therefore, using the compounds or compositions described in the present invention as mulberry looper attractants for trapping mulberry loopers can achieve efficient trapping of mulberry loopers, is green and environmentally friendly, has high specificity, is safe and efficient, and has great development prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figure 1 This is the result of EAG reaction experiment at different doses of single-component compound.

[0019] Figure 2 This is the EAG reaction test result diagram under different ratios of two-component compositions.

[0020] Figure 3 This is the EAG reaction test result diagram of the three-component composition with different ratios. DETAILED DESCRIPTION

[0021] The present invention is further explained below with reference to specific examples, but the examples do not limit the present invention in any form.

[0022] The present invention prepares a composition by adding the sex pheromone (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene (compound 1) and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene (compound 2) and the synergist ionone, and screens the optimal composition ratio through the EAG reaction.

[0023] Before the experiment, the antennae of male mulberry loopers were cut from the base. A small section of the antennae's end was trimmed with a single-edged razor blade. The antennae were then fixed to a metal electrode with conductive glue and inserted into an EAG probe. Once the baseline stabilized, the experiment began. A long strip of filter paper (0.5 cm × 3 cm) was folded in half lengthwise and partially inserted into the wide end of a Pasteur tube. The test compound was then dropped onto the filter paper and, after evaporation, completely inserted into the tube for EAG reaction. In all the experiments described above, male mulberry loopers were two-day-old and unmated. Each treatment was tested three times on the same antennae, for a total of four antennae. Only one antennae from each male was used. The order of the test treatments was randomized, and the order of stimulation was from low to high for dose determination. In order to eliminate the deviation caused by antennal adaptation, n-hexane was used as a blank control before and after the test. The average EAG response value obtained in each test was subtracted from the average EAG response value of the blank control before treatment (blank A) and after treatment (blank A+1) to obtain the net response value each time.

[0024] Example 1 EAG response of male A. mori to different doses of synthetic compounds

[0025] The compounds used in the determination of the antennal potential response were mixed with n-hexane as the solvent, and compound 1, compound 2 and ionone were respectively configured into four concentrations of 10 μg / mL, 1 μg / mL, 0.1 μg / mL and 0.01 μg / mL; compound 1, compound 2 and ionone were mixed in a mixing ratio of 1:1:1 for testing. The concentrations were 10 μg / mL, 1 μg / mL, 0.1 μg / mL and 0.01 μg / mL, respectively, and 100 μL of each single component and mixed component was taken for testing, and the doses were 1 μg, 0.1 μg, 0.01 μg and 0.001 μg, respectively, and the testing order of the same treatment was from low dose to high dose.

[0026] The results are shown in Table 1: Figure 1 The EAG dose of the single component showed that the antennal potential response value of the three compounds was the largest at a dose of 0.1 μg, reaching the peak value. With the increase of the dose to 1 μg, the antennal potential response values of compound 1 and ionone tended to be stable, and the value of compound 2 decreased to 0.42 mV. This indicates that the reaction threshold of compound 2 to the male A. mori antennae is relatively low, and a large dose will cause the reaction of the male A. mori antennae to decrease.

[0027] Example 2 EAG response of male A. mori to different proportions of the combined compounds

[0028] First, compound 1 and compound 2 were configured into a 1 μg / mL solution. Double-component solutions with different mass ratios were configured according to the test requirements, and the ratios were as follows:

[0029] Compound 1: compound 2 = 1:1;

[0030] Compound 1: compound 2 = 5:1;

[0031] Compound 1: compound 2 = 10:1;

[0032] Compound 1: compound 2 = 15:1;

[0033] Compound 1: compound 2 = 1:5;

[0034] Compound 1: compound 2 = 1:10;

[0035] Compound 1: compound 2 = 1:15;

[0036] Each of the above compositions was taken for testing in an amount of 100 μL, and the results are shown in Table 2: Figure 2As shown, all seven compositions with different ratios can produce EAG reactions. In the two-component test with different ratios, when compound 1:compound 2 = 1:10, the highest EAG reaction value is 1.26 mV.

[0037] Example 3 EAG response of male mulberry looper to compositions of different ratios

[0038] First, compound 1, compound 2, and ionone were prepared into a 1 μg / mL solution in n-hexane. According to the experimental requirements, compound 1, compound 2, and ionone were prepared into different mass ratios of the composition solution, respectively labeled as composition AG, with the following ratios:

[0039] Composition A = 1:10:1

[0040] Composition B = 1:10:3

[0041] Composition C = 1:10:5

[0042] Composition D = 1:10:7

[0043] Composition E = 1:10:9

[0044] Composition F = 1:10:11

[0045] Composition G = 1:10:0.5

[0046] 100 μL of each of the above composition solutions was taken for testing. The results were as follows: Figure 3 As shown in the figure: 7 compositions with different proportions of the three components can all produce EAG reactions. In the test of different proportions of the ternary components, when the composition D, i.e., compound 1: compound 2: ionone, is 1:10:7, the antennal potential caused is the highest, and the EAG reaction value is the highest at 2.82mV. As the proportion of ionone continues to increase, the EAG reaction value decreases instead. The EAG reaction value of the three components is much higher than the EAG reaction value of the two-component compound 1: compound 2 = 1:10, while the EAG reaction value of ionone itself is relatively low. It can be concluded that ionone mainly plays a synergistic role and is indispensable.

[0047] In summary, the EAG reaction results show that male mulberry loopers' antennae are more sensitive to compound 2, indicating that compound 2 plays a primary role in eliciting male mulberry loopers' sexual behavioral responses. Compound 1 and ionone play a supporting role in eliciting male mulberry loopers' sexual behavioral responses. When the three compounds are combined in appropriate proportions, the EAG response is significantly increased. However, the overall EAG response produced by the mixture is not a simple summation of the EAG responses of the individual components alone; instead, it exhibits a significant synergistic effect, demonstrating the complexity of the mulberry looper's sex pheromone sensing system.

[0048] Most lepidopteran insects exhibit minimum and maximum threshold responses to sex pheromones. The dose-response curves for each sex pheromone component in male mulberry loopers (E. serrata) exhibited a roughly S-shaped pattern. The EAG response was low at a dose of 0.001 μg. The EAG response increased significantly with increasing dose, reaching a maximum at 0.1 μg. However, the increase in EAG response slowed and even declined at 1 μg, suggesting a potential saturation effect or adaptive inhibition of the receptor. Furthermore, the EAG response for the 1:10 ratio of Compound 1: Compound 2 was the highest among the two-component combinations, while the 1:10:7 ratio of Compound 1: Compound 2: Ionone elicited the highest antennal potential. All EAG response values ​​for the three-component combination were higher than those for the 1:10 ratio of Compound 1: Compound 2. This suggests that ionone exhibits a significant synergistic effect in trapping mulberry loopers with sex pheromones, with the optimal ratio being 1:10:7.

Claims

1. Use of a compound in the preparation of a mulberry looper attractant, characterized in that: The compound is selected from (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene, (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene or ionone.

2. A composition, characterized in that The composition comprises (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene.

3. The composition according to claim 2, characterized in that The mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene is 1-20:1-20.

4. The composition according to claim 3, characterized in that The mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene is 1-15:1-15.

5. The composition according to claim 3, characterized in that The mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene is 1:1 to 15.

6. The composition according to claim 3, characterized in that The mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene and (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene is 1:

10.

7. The composition according to claim 2, characterized in that The composition also includes ionone.

8. The composition according to claim 7, characterized in that The mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene, (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene and ionone in the composition is 1:5-15:1-15.

9. The composition according to claim 7, characterized in that The mass ratio of (6Z, 9S, 10R)-9,10-epoxyoctadec-6-ene, (3Z, 6Z, 9S, 10R)-9,10-epoxyoctadec-3,6-diene and ionone in the composition is 1:10:

7.

10. Use of the composition according to any one of claims 2 to 9 in the preparation of an attractant for geometrids.

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