JP3577501B2 - Sex attractant for heptophila picea belonging to the family Scarabaeidae - Google Patents

Description

[0001]
TECHNICAL FIELD OF THE INVENTION
[0002]
TECHNICAL FIELD The present invention relates to an attractant for heptophila picea (scientific name: Heptophylla picea) belonging to the order Coleoptera, Scarabaeidae, and more particularly, to a sex attractant effective for controlling heptophila picea.
[0003]
[Prior art]
[0004]
Adults of Heptophila picea belonging to the order Coleoptera, Scarabaeidae, mainly occur in Honshu and Hokkaido, and damage the leaves of cedar, cypress, larch, etc. ing.
[0005]
It is very difficult to prevent or control the damage caused by heptophila with conventional insecticides, and in view of the current situation, in order to effectively control this pest, it is necessary to know its occurrence accurately. There is a strong demand for new forecasting means and new types of control means different from conventional insecticides.
[0006]
On the other hand, the chemical structure of sex pheromones and assembled pheromones has been elucidated for many pests.
[0007]
Depending on the type of pests, these pheromone agents can be used to effectively investigate the emergence of these pheromones.In addition, these attractants can be used to capture large amounts of adults and to confound the sex of males and females. In addition, methods of controlling pests by doing so are being developed.
[0008]
[Problems to be solved by the invention]
[0009]
However, there is no known sex attractant effective for controlling heptophila care.
[0010]
Therefore, a sex attractant excellent in controlling effect of heptophila care has been desired.
[0011]
[Means for Solving the Problems]
[0012]
Under such a background, the present inventors conducted research on the sex pheromone of heptophila pica, and extracted a component having an attractive property to the male adult from a female adult of heptophila picea, and obtained the active ingredient substance. The present inventors have elucidated the chemical structure of the compound, and have found that the compound synthesized based on the chemical structure exhibits an effective attracting effect on adult male heptophila picea, thereby completing the present invention.
[0013]
That is, means for solving the problems of the present invention are as follows.
[0014]
First, a sex attractant for heptophilapicare, containing (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] as an active ingredient.
[0015]
Secondly, a sex attractant for heptophila picare, in which a compound containing (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] as an active ingredient is supported by a device.
[0016]
(R, Z) -Hexadeca-7,15-diene-4-olide [(R) -enantiomer], which is an active ingredient of the attractant according to the present invention, has an attractive effect and a behavioral stimulus for male adult heptophylla pikea. Show action.
[0017]
In order to prepare the attractant according to the present invention, (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] is used for the preparation of a general attractant. It can be done using any formulation technology.
[0018]
For example, (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] is used as it is or as a solution using an organic solvent such as dichloromethane, and this solution is used as a suitable device such as polyethylene. It can be made into a practical form of attractant by adsorbing it on plastic or rubber, etc., or by using an appropriate material or device according to the plastic capsule or capillary mode.
[0019]
Embodiment 1
[0020]
Hereinafter, an example of the attractant according to the present invention will be described.
[0021]
First, in order to identify the sex-inducing component of heptophila picea belonging to the family Scarabaeidae, we used a bioelectric detector directly connected to a gas chromatograph to detect the change in nerve potential that occurs when the tactile sense receives the active substance. Followed by detection method (GC-EAD).
[0022]
An adult female of Heptophila picea collected outdoors was left in the dark for 30 minutes and then immersed in hexane for 3 minutes to obtain an extract thereof.
[0023]
The extract was developed by silica gel flash column chromatography with a hexane-ether mixed solvent (100: 0, 95: 5, 90:10, 80:20, 50:50, 0: 100) to give hexane-ether (80:20). EAD active substance was found in the fraction of ()). This fraction was again subjected to silica gel flash column chromatography to obtain an EAD active substance having a purity of 97% or more.
[0024]
From the tracer GC-FTIR (FIG. 1) of this EAD active substance, an oxacyclopentan-2-one ring (1772 cm ⁻¹ ), a terminal double bond (3073 cm ⁻¹ & 1641 cm ⁻¹ ) and a cis double bond (3002 cm ^−). The presence of ¹ ) was suggested.
[0025]
Although no molecular ion peak was measured from the GC-MS of this EAD active substance, 7-hexadecene-4-olide (FIG. 2) and 15-hexadecene were determined from the mass spectrum of the DMDS derivative of the hydrogenation product of diimide. The existence of two types of monoene compounds of -4-olide (FIG. 3) and a saturated compound of hexadecane-4-olide was confirmed, and the EAD active substance was confirmed to be hexadec-7,15-diene-4-olide. Was done.
[0026]
Furthermore, when hexadecane-4-olide obtained by reducing the racemic form of hexadec-7,15-diene-4-olide was injected into a Chiraldex GTA column, two peaks appeared at 44.99 min and 46.5 min, and the previous peak appeared. Corresponds to the peaks of the active natural product and the separately synthesized reduction product of (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer]. The body was confirmed.
[0027]
Further, when (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] separately synthesized was compared with an HP-INNOWAX column and an HP-5MS column, it was found to be the active natural product. .
[0028]
From the above results, the substance (natural product) exhibiting an extremely high attracting effect on heptophila picea belonging to the order Coleoptera, Scarabaeidae is (R, Z) hexadec-7,15-diene-4-olide [(R)- Enantiomers].
[0029]
The (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] obtained by chemical synthesis was subjected to gas chromatography / direct contact antenna potential detector (GC-EAD). However, the EAD response could be clearly recorded.
[0030]
Next, a sex attractant according to the present invention was prepared using (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer].
[0031]
Then, the sex attractant (1 mg) was impregnated into a pellet made of a copolymer of ethylene vinegar vinyl to obtain a sex attractant A according to the present invention.
[0032]
[Comparative Example 1]
[0033]
(R, Z) -hexadeca-7,15-diene-4-olide [(R) -enantiomer] and (S, Z) -hexadeca-7,15-diene-4-olide [(S) -enantiomer] Was mixed at a ratio of 50:50 to prepare a sex attractant.
[0034]
Then, the sex attractant (1 mg) was impregnated into a pellet made of an ethylene-vinyl acetate copolymer to obtain a sex attractant B according to Comparative Example 1.
[0035]
[Comparative Example 2]
[0036]
A sex attractant was prepared with (S, Z) -hexadec-7,15-diene-4-olide [(S) -enantiomer].
[0037]
Then, the sex attractant (1 mg) was impregnated into a pellet made of an ethylene-vinyl acetate copolymer to obtain a sex attractant C according to Comparative Example 2.
[0038]
[Test Example 1]
[0039]
As a section of the present invention, ten plastic containers containing the sex attractant A obtained in Example 1 were prepared.
[0040]
As a control 1, ten plastic containers containing the sex attractant B obtained in Comparative Example 1 were prepared.
[0041]
As a control group 2, ten plastic containers containing the sex attractant C obtained in Comparative Example 2 were prepared.
[0042]
As a control 3, 10 empty plastic containers were prepared in which nothing was put.
[0043]
The 10 plastic containers of each section prepared above were each set in an adhesive trap, and 10 traps were prepared for each section.
[0044]
Using these traps, a trap test of heptophila picea was carried out from July 10 to July 11 in the Kyodo Shoji Lilac field in Sapporo, Hokkaido, under the same environmental conditions. Was determined.
[0045]
The results of the test were as follows.
[0046]
The average number of insect traps per trap in the plot of the present invention was 36 / hour.
The average number of traps per trap in the control section 1 was 1.0 per 1 hour.
The average number of traps per trap in the control section 2 was 0.85 per hour.
The average number of insect traps per trap in the control section 3 was 0.32 animals / hour.
[0047]
As shown in the above results, the group of the present invention showed strong attraction to heptophila pica.
[0048]
Considering the results of the above test examples, it was confirmed that the attractant according to the present invention had an extremely high attracting effect on male adult Heptophilapia belonging to the order Coleoptera, Scarabaeidae.
[0049]
【The invention's effect】
[0050]
ADVANTAGE OF THE INVENTION According to the sex attractant of this invention, it has high attraction effect with respect to the male adult of heptophila picea, and is excellent in the control effect of heptophila picea.
[Brief description of the drawings]
1 shows a spectrum of a tracer GC-FTIR. FIG. 2 shows a mass spectrum of a DMDS derivative with respect to 7-hexadecene-4-olide. FIG. 3 shows a mass spectrum of a DMDS derivative with respect to 15-hexadecene-4-olide.

Claims (2)

A sex attractant for heptophilapicare belonging to the family Scarabaeidae, which comprises (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] as an active ingredient. A sex attractant for heptophilapicare belonging to the family Scarabaeidae, in which a compound containing (R, Z) -hexadec-7,15-diene-4-olide [(R) -enantiomer] as an active ingredient is supported by a device.

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