JPH1149607A - Attractant for piezodorus hybneri - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject attractant, capable of manifesting high attracting actions on male and female imagoes of Piezodorus hybneri and effective in controlling thereof by including a specific compound such as β-sesquiphellandrene as an active ingredient therein. SOLUTION: This attractant is obtained by carrying out research on a sex pheromone of Piezodorus hybneri belonging to the family Pentatomidae of the order Hemiptera, taking out an ingredient having attracting properties for the male and female imagoes thereof from a male imago of the Piezodorus hybneri, elucidating the chemical structure of the active ingredient substance, directly using β-sesquiphellandrene, methyl-8-(Z)-hexadecenoate and (R) 15- hexadecanolide synthesized on the basis of the chemical structure at (9.0-11.0):(3.0-5.0):(0.5-1.5), preferably 10:4:1 ratio or converting the compounds into a solution by using an organic solvent, adsorbing the prepared solution on a plastic, a rubber, etc., or providing a practical form by using a capsule made of the plastic, a suitable material or a tool according to a capillary mode.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD OF THE INVENTION

[0002] The present invention relates to an attractant for the stink bug (Piezodorushybneri) belonging to the order Hemiptera, and more particularly to an attractant effective for controlling the stink bug, Streptomyces.

[0003]

[Prior art]

[0004] Adults of the stink bug, Hemiptera, belong to the family Hemiptera and occur throughout East Asia, Australia, and Africa, including Japan, and cause great damage to beans such as soybean and adzuki bean.

[0005] It is very difficult to prevent or control the damage caused by this bug, which is very difficult with conventional insecticides. Under such circumstances, in order to control this pest effectively, its generation is precisely determined. Therefore, there is a strong demand for a new type of control means and a new type of control means different from conventional insecticides.

On the other hand, until now, many pests have
The chemical structures of sex pheromones and assembled pheromones have been elucidated.

[0007] Depending on the type of pest, the use of these pheromone agents makes it possible to carry out effective investigations on the occurrence and fate of the pheromone. Furthermore, using these attractants, it is possible to capture a large amount of adults and to mate male and female. Methods for controlling pests by disturbing their behavior are also being developed.

[0008]

[Problems to be solved by the invention]

[0009] However, no attractant is known which is effective for controlling the stink bugs.

[0010] Therefore, there has been a demand for an attractant which has a high attracting effect on adult males and females of the stink bug, which can be effectively used for control.

[0011]

[Means for Solving the Problems]

Under these circumstances, the present inventors have
A study on the sex pheromone of the stink bug, a male of the stink bug, a component with an attractive property to its male and female adults was taken out, the chemical structure of the active ingredient substance was clarified, and the compound synthesized by the chemical structure was used. The present inventors have found that they exhibit an effective attraction effect on adult males and females of the stink bug, and have completed the present invention.

That is, means for solving the problems of the present invention are as follows.

First, β-sesquiferrandrene, methyl-8- (Z) -hexadecenoate, (R) -15-
An attractant for the stink bug, containing hexadecanolide as an active ingredient. Second, β-sesquiferrandrene (referred to as βSP), methyl-8- (Z) -hexadecenoate (referred to as M8ZHD), and (R) -15-hexadecanolide (referred to as R15HDL) are represented by βSP:
M8ZHD: R15HDL = 9.0 to 11.0: 3.0
5.0: a attractant for Stinkbug, containing a compound prepared to be 0.5 to 1.5. Third, β
A compound containing sesquiphelandrene, methyl-8- (Z) -hexadecenoate, (R) -15-hexadecanolide as an active ingredient, was loaded on a device;
An attractive agent of the stink bug. Fourth, β-sesquiferrandrene (referred to as βSP), methyl-8- (Z) -hexadecenoate (referred to as M8ZHD), (R) -15
-Hexadecanolide (R15HDL) is converted to βS
P: M8ZHD: R15HDL = 9.0 to 11.0:
3.0 to 5.0: a compound prepared to be 0.5 to 1.5, loaded on a device, and an attractant for Stinkbugs.

Regarding the above second and fourth, βSP, M
The mixing ratio of 8ZHD and R15HDL is βSP: M8Z
HD: R15HDL = 9.0-11.0: 3.0-5.
0: 0.5 to 1.5, preferably βSP: M8ZH
D: R15HDL = 10: 4: 1.

The active ingredient of the attractant according to the present invention, β
-Sesquiferandrene (β-Sesquiphellandrene),
Methyl-8- (Z) -hexadecenoate [Methyl-8-
(Z) -hexadecenoate] and (R) -15-hexadecanolide [(R) -15-Hexadecanolide] exhibit an attracting action and a behavioral stimulating action on male and female adults of the stink bug, Streptomyces.

That is, β-sesquiphelandrene, methyl-8- (Z) -hexadecenoate, (R) -15
-Hexadecanolide is composed of each component alone or 2
Even when the components are combined, it has an effect as an attractant for the stink bug.

Further, even when any one of β-sesquiferrandrene, methyl-8- (Z) -hexadecenoate and (R) -15-hexadecanolide is used alone, Has an effect as a sex pheromone.

To prepare the attractant according to the present invention, β
-Sesquiphelandrene, methyl-8- (Z) -hexadecenoate, and (R) -15-hexadecanolide, which can be carried out by using a usual technique for preparing a sex attractant.

For example, β-sesquiferrandrene, methyl-8- (Z) -hexadecenoate, (R) -15-
Hexadecanolide is used as it is or as a solution using an organic solvent such as dichloromethane, and the solution is adsorbed on a suitable device, for example, plastic or rubber such as polyethylene, or an appropriate solution according to the plastic capsule or capillary mode. A practical form of attractant can be obtained by using various materials or tools.

[0021]

【Example】

In order to identify the attractant components, the components were tracked using a bioelectric detector directly connected to a gas chromatograph to detect changes in nerve potential generated when the antennae received the active substance.

After field collection, the bred male adult stink bug is housed in a glass container, and the air around the male adult is kept at 25 ° C. in daylight for 16 hours in a dark place while supplying clean air. 8 hours with Super Q column (Alltech, Dee
field, IL).

Thereafter, an extract was obtained by passing hexane through a Super Q column.

When this extract was analyzed by gas chromatography, many components were found.

When the active components were examined by gas chromatography / direct contact antenna potential detector method (GC-EAD), three EAD active peaks were observed.

These three components were injected into a gas chromatograph-directed mass spectrometer (GC-MS analysis).
-Sesquiferrandrene, methyl-8- (Z) -hexadecenoate, (R) -15-hexadecanolide.

These three components were found to be sex pheromones that not only attract male and female adults, but also induce mating behavior of male adults.

Separately synthesized β-sesquiphelandrene, methyl-8- (Z) -hexadecenoate, (R)
Comparison of -15-hexadecanolide was consistent with the active natural product.

From the above results, substances (natural products) exhibiting an extremely high attracting effect on the stink bugs belonging to the order Hemiptera are described as β-sesquipherandrene, methyl-8- (Z) -hexadeceno Eat, (R) -15
-It was determined to be hexadecanolide.

It is to be noted that β-sesquiphelandrene, methyl-8- (Z) -hexadecenoate and (R) -15-hexadecanolide obtained by chemical synthesis were subjected to gas chromatography / direct contact antenna potential detector. When applied to (GC-EAD), the response of EAD was clearly recorded.

An example of the attractant according to the present invention will be described below.

[0033]

Embodiment 1

Β-sesquiferrandrene (hereinafter referred to as βSP), methyl-8- (Z) -hexadecenoate (M8
ZHD), (R) -15-hexadecanolide (R15HDL) was converted to βSP: M8ZHD: R1
By setting 5HDL = 10: 4: 1, the attractant A1 according to the present invention was prepared.

[0035]

Embodiment 2

In the same manner as in Example 1, β-sesquiferrandrene (referred to as βSP), methyl-8- (Z) -hexadecenoate (referred to as M8ZHD), (R) -15-hexadecanolide (referred to as M8ZHD) R15HDL) as βSP: M8
The compound was prepared by making ZHD: R15HDL = 10: 4: 1. 500 ηg of this compound
The attractant A2 according to the present invention was prepared by impregnating the filter paper.

[0037]

Embodiment 3

Β-sesquiphelandrene (hereinafter referred to as βSP), methyl-8- (Z) -hexadecenoate (M8
ZHD) was adjusted to βSP: M8ZHD = 10: 4 to prepare the attractant B1 according to the present invention.

[0039]

Embodiment 4

In the same manner as in Example 3, β-sesquiferandrene (referred to as βSP) and methyl-8- (Z) -hexadecenoate (referred to as M8ZHD) were converted to βSP: M8ZHD.
= 10: 4 to prepare the compound. The attractant B2 according to the present invention was prepared by impregnating the filter paper with 500 ηg of this compound.

[0041]

Embodiment 5

Β-sesquiferrandrene (referred to as βSP), (R) -15-hexadecanolide (R15HD
L) was changed to βSP: R15HDL = 10: 1 to prepare the attractant C1 according to the present invention.

[0043]

Embodiment 6

In the same manner as in Example 5, β-sesquiferrandrene (referred to as βSP) and (R) -15-hexadecanolide (referred to as R15HDL) were converted to βSP: R15HDL =
The compound was prepared at 10: 1.
The attractant C2 according to the present invention was prepared by impregnating the filter paper with 500 ηg of this compound.

[0045]

Embodiment 7

Methyl-8- (Z) -hexadecenoate (referred to as M8ZHD) and (R) -15-hexadecanolide (referred to as R15HDL) were converted to M8ZHD: R15HD.
By setting L = 4: 1, the attractant D1 according to the present invention was prepared.

[0047]

Embodiment 8

As in Example 7, methyl-8- (Z)-
Hexadesenoate (M8ZHD) and (R) -1
5-hexadecanolide (R15HDL) was converted to M8
The compound was prepared by making ZHD: R15HDL = 4: 1. The attractant D2 according to the present invention was prepared by impregnating the filter paper with 500 ηg of this compound.

[0049]

Embodiment 9

500 ηg of β-sesquiferrandrene is
The attractant E1 according to the present invention was prepared by impregnating the filter paper.

[0051]

Embodiment 10

The attractant F1 according to the present invention was prepared by impregnating 500 ηg of methyl-8- (Z) -hexadecenoate into filter paper.

[0053]

Embodiment 11

(R) -15-hexadecanolide 500
The attractant G1 according to the present invention was prepared by impregnating filter paper with ηg.

[0055]

[Test Example 1]

As a section of the present invention, two attractants A2 obtained in Example 2 were prepared.

As a control, two filter papers which were not impregnated with anything were prepared.

The filter papers of the respective sections prepared as described above were set in an indoor olfactometer, and bioassay was performed twice under the same environment using male and female adults of Streptomyces.

Then, the average of two times of the adult stink bug, male and female, was determined by bioassay using an olfactometer within a predetermined time, and the result of the attraction test is shown in FIG.

The present invention (shown as pheromone in FIG. 1) has an attracting effect on 36% of adult males as shown in A of FIG. As shown, it had an attractive effect on 20% of the female adults.

On the other hand, in the control group, 0.
It only had an attraction effect of 8% and 0.6% against female adults.

[0062]

[Test Example 2]

As the present invention section 1, one attractant A2 obtained in the above Example 2 was prepared.

Also, as the present invention sections 2 to 7, the fourth embodiment,
B2, C2, D obtained in 6, 8, 9, 10 and 11
2, one each of E1, F1, and G1 were prepared.

The filter paper of each section prepared above was set in an indoor olfactometer, and bioassay was carried out under the same environment using a male adult stink bug,
The attracting rate of adult stink bugs to male adults and the mating rate of male adult stink bugs were examined.

FIG. 2A shows the attraction rate of the adult stink bug, male, and FIG. 2B, the mating activity rate of the adult stink bug, within a predetermined period of time.

As shown by A in FIG. 2, the present invention section 1 (shown as three components in FIG. 2) has an attracting effect on 32% of male adult stink bugs. As shown in B of 2, 49% of the adult males exhibited mating behavior.

Similarly, the present invention section 2 (M8ZHD in FIG. 2)
+ ΒSP) as shown in A of FIG.
It has an attracting effect on 10.6% of male adult stink bugs, and as shown by B in FIG.
3.1% showed mating behavior.

Similarly, the present invention section 3 (R15HD in FIG. 2)
L + βSP) has an attracting effect on 10.4% of male adult stink bugs as shown in A in FIG. 2, and as shown in B in FIG. 37.2% exhibited mating behavior.

Similarly, the present invention section 4 (R15HD in FIG. 2)
L + M8ZHD), as shown in A of FIG. 2, has an attracting effect on 12.0% of male adult stink bugs, and as shown in B of FIG. 34.8% exhibited mating behavior.

Similarly, the present invention section 5 (shown as βSP in FIG. 2) has an attracting effect on 11.3% of male adults of the stink bug, as shown by A in FIG. As shown by B in FIG. 2, 25.9% of male adults showed mating behavior.

Similarly, the present invention section 6 (M8ZHD in FIG. 2)
2) has an attracting effect on 10.6% of male adult stink bugs as shown in A of FIG. 2 and, as shown in B of FIG. 34.8
% Showed mating behavior.

Similarly, the present invention section 7 (R15HD in FIG. 2)
L) has an attracting effect on 0.7% of male adult stink bugs, as shown in A in FIG. 2, and as shown in B in FIG. 34.5
% Showed mating behavior.

Considering the above results, the present invention section 1
It was confirmed that the effects of the present invention were even better than those of the present invention.

Therefore, it was confirmed that the attractant according to the present invention has an extremely high attracting effect on adult males and females of the stink bug, Hemiptera.

[0076]

【The invention's effect】

According to the attractant of the present invention, it has a high attracting effect on adult males and females of the stink bug, and can be effectively used for control.

[Brief description of the drawings]

BRIEF DESCRIPTION OF DRAWINGS FIG. 1 is a graph showing the results of an attraction test on adult males and females of Stinging bugs by bioassay using an olfactometer.

FIG. 2 is a graph showing the results of an attraction test for male adult stink bugs and a mating behavior test of male adults by bioassay using an olfactometer.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Mikio Ono 3-5-8 Midorigaoka, Hamura-shi, Tokyo Inside Fujiflavor Co., Ltd.

Claims (4)

[Claims] 1. β-sesquiferrandrene, methyl-8
-An attractant for the stink bug, comprising (Z) -hexadecenoate and (R) -15-hexadecanolide as active ingredients. 2. β-sesquiferrandrene (hereinafter referred to as βSP), methyl-8- (Z) -hexadecenoate (M8
ZHD), (R) -15-hexadecanolide (R15HDL) was converted to βSP: M8ZHD: R1
5HDL = 9.0-11.0: 3.0-5.0: 0.5
An attractant for the stink bug, containing a compound prepared to be 1.5. 3. β-sesquiferrandrene, methyl-8
-An attractant for Stinging Bugs, in which a compound containing (Z) -hexadecenoate and (R) -15-hexadecanolide as an active ingredient is supported by a device. 4. β-sesquiferrandrene (hereinafter referred to as βSP), methyl-8- (Z) -hexadecenoate (M8
ZHD), (R) -15-hexadecanolide (R15HDL) was converted to βSP: M8ZHD: R1
5HDL = 9.0-11.0: 3.0-5.0: 0.5
An attractant for the stink bug, wherein the compound prepared so as to be 1.5 is supported on a device.