JP2720378B2 - Attractant of the stink bug - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an attractive agent of a stink bug, Streptomyces stigma.

[0002]

2. Description of the Related Art Platia
stali Scott) is an important pest of fruit trees.
The pest prefers to suck on fruit, causing fruit malformation and fruit dropping. The main sources are cypress and cedar forests that invade orchards during the migration process. Since it is extremely difficult to control forests, it is necessary to control them at the adult stage. Such control is usually carried out by spraying an organic synthetic pesticide, but it is desirable to avoid this from the viewpoint of environmental pollution and residual pesticides.

[0003]

On the other hand, the chemical structure of so-called sex pheromones has been elucidated for many pests in recent years. Became. Although the existence of such sex pheromone has not been confirmed in this species,
It is considered that an assembling pheromone exists because male adults exhibit species-specific attraction to male and female adults of the same species. By elucidating the chemical structure of the pheromone in such an assembly, chemically synthesizing this substance, and using it as an attractant, it becomes possible to efficiently investigate the occurrence and fate. Furthermore, it is considered possible to control pests for the adult stage by inducing a large amount of adults using this attractant. In view of these circumstances, the present inventors have studied the collective pheromone of the leaf stink bug, and extracted components having attraction activity for male and female adults from the male adult stink bug, and determined the chemical structure thereof. The present invention has been completed based on these findings.

[0004]

SUMMARY OF THE INVENTION The present invention is directed to a 2,4,6-
An object of the present invention is to provide an attractant for a green stink bug, containing methyl decatrienoate. It is presumed that the double bond at position 6 of this compound is cis and the double bonds at positions 4 and 2 are trans.

When the compound of the present invention is used as an attractant, various forms of use are possible. Since these compounds are extremely effective in a very small amount and are volatile, they can be adsorbed on appropriate carriers (synthetic polymers, natural rubber, synthetic rubber, etc.) or molded into these carrier materials. It is preferable to use it in a form enclosed in a product. The content of the active ingredient can be appropriately determined, but when it is adsorbed on a carrier or encapsulated in a molded carrier material, the content is preferably about 0.1 to 100 mg per 1 g of the carrier.

[0006] A carrier or a carrier material molded product containing such an active ingredient is placed on a suitable support, for example, on a container filled with water or other liquid, or on an object coated with a suitable adhesive substance, or the like. By being installed in the vicinity, the attracted German green stink bugs die in the container or are caught by the sticky substance and die.

The present invention will be described in detail below step by step.
In order to elucidate the chemical structure of the assembled pheromone substance of the green stink bug, the components having attracting activity were first collected by circulating the air in a container containing male adults through an adsorbent (Polapack Q). The attraction activity was determined by the number attracted to the sample in the field and killed by the basin.

The acetone solution of the collected substance from about 100,000 males was concentrated, dehydrated, and fractionated by column chromatography using a column packed with florisil. 5% active ingredient
Eluted with ether / hexane. This active fraction was further fractionated by high performance liquid chromatography using a silica gel column. The active ingredient was eluted with 5% ether / hexane between a retention time of 10 and 11.5 minutes. Then, the active fraction was purified by gas chromatography. When a FFAP megabore column was used, activity was observed in the fraction containing the peak at 13.6 minutes.

Next, the following analysis was performed to determine the chemical structure of this component. The isolated components were analyzed with a gas chromatography mass spectrometer to obtain a mass spectrum. The spectrum revealed that the molecular weight was 180 (M / Z (relative intensity), EI: 79 (100), 1
80 (94)). Since the molecular weight increased by 6 by hydrogenation, it was found that there were three double bonds. The hydrogenated product was estimated to be methyl decanoate from the obtained mass spectrum. The isolated component was partially hydrogenated to localize the double bond and the resulting product was treated with dimethyl disulfide to modify the double bond. From the obtained mass spectrum, the position of the double bond was at the 4- and 6-positions, and the geometric isomers were estimated to be trans and cis. But,
No modified product derived from another double bond was detected. Therefore, the active ingredient was reduced to alcohol and then changed to acetate. This was partially hydrogenated and the resulting product was treated with dimethyl disulfide to modify the double bond. From the obtained mass spectrum, the unknown double bond was at the 2-position, and was presumed to be a trans bond. From the above, it was presumed that the assembled pheromone substance of the green stink bug was (E, E, Z) methyl 2,2,4,6-decatrienoate.

The attraction effect of the attractant of the present invention on the green stink bug is shown in Test Examples. Test Example 1 The attracting activity of the fraction obtained by chromatography was confirmed outdoors. The test was performed as follows. A basin trap with a 3 cm long cotton rope impregnated with an amount equivalent to the amount of emissions from 30 males,
It was set up at the spot where the Chambera stink bug can be seen. As a control, a trap using a net basket containing male adults as an attraction source was used. Table 1 shows the results.

Test Example 2 The attracting activity of the active ingredient purified from the collected material from 30 adult males was confirmed in the field. The test was performed as follows. An adhesive trap using a cotton rope impregnated with a compound in a length of 3 cm as an attraction source was installed at a point where a flying stink bug could be seen. As a control, a trap using a net basket containing male adults as an attraction source was used. Table 2 shows the results.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Hiroshi Noguchi 343 Sanuki-cho, Ryugasaki-shi, Ibaraki Prefecture (72) Inventor Kenjiro Kawasaki 668-23 Shimohirooka, Tsukuba-shi, Ibaraki Prefecture (72) Inventor Kazuo Takagi Azuma, Tsukuba-shi, Ibaraki Prefecture 2-711 No. 702 (72) Inventor Seiichi Moriya 4-222, Shurizakiyamacho, Naha City, Okinawa Prefecture (72) Inventor Azusa Fujiya 256-3, Kami Market, Mutsawa-cho, Nagao-gun, Chiba Prefecture (72) Inventor Hiroshi Fukuda Chiba 4-54, Ayumino, Midori-ku, Chiba-shi, Japan 3 (72) Inventor Yoshio Ohira 1169-2, Futsukaichi, Chikushino-shi, Fukuoka (72) Inventor Katsuo Tsuda 1169-2, Futsukaichi, Chikushino-shi, Fukuoka (72) Masahiro Yamanaka Shizuoka, Japan 1-20-20 Orito, Shimizu-shi (72) Inventor Takafumi Tsutsumi 17-60 Togumae, Iizuka-shi, Fukuoka Prefecture (72) Inventor Hiroshi Suzuki 8-7-138 Nakamon-cho, Joetsu-shi, Niigata Prefecture (72) Inventor Takehiko Fukumoto 5-401, Sanai-cho, Joetsu-shi, Niigata (56) References PHYTOCHEMSTRY, VOL. 20 (1981), NO. 1, P. 89−91

Claims (1)

(57) [Claims] 1. An attractive attractant for sting bugs comprising methyl 2,4,6-decatrienoate or methyl (E, E, Z) -2,4,6-decatrienoate as an active ingredient.