JPH1179908A - Sexual lure of cotton helicopter - Google Patents

Abstract

(57) [Summary] [Problem] To develop a sex attractant useful for controlling or outbreak control of cotton helicopter, Rhipicephalus velutipes. SOLUTION: (E) -11-hexadecenal and (E, E) -10,12-hexadecadienal, which are component substances of the sex pheromone secretion liquid of a female adult of the cotton moth, Pleurotus terrestris, are used as active ingredients. Attractant.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a sex attractant which is useful for controlling a cotton moth, which belongs to the order Lepidopteridae, or for investigating the occurrence.

[0002]

[Background Art] Cotton helicopter (Diaphania)
indica (Saunders) is also an insect belonging to the Lepidoptera, Pyralidae, and is a crop pest that damages Cucurbitaceae crops. Until now, this type of control has been mainly carried out by spraying insecticides, but recently, with the aim of breaking away from insect pest control systems that rely solely on pesticides, the use of behavior control substances and natural enemies has been It is necessary to develop a control method with less adverse effects. In addition, in order to effectively use insecticides, it is important to know exactly when pests occur.

On the other hand, recently, the chemical structure of sex pheromones has been elucidated for many pests, and the investigation of the occurrence and fate of the pests using the attractive sex pheromone can be performed efficiently. Furthermore, methods for controlling pests by using this sex attractant to capture large amounts of adult males or to disrupt male and female mating behaviors are being developed (Kenji Umeya, "Insect Industry": Agriculture, Forestry and Fisheries Technology Information Association, 1997
Such). In view of these circumstances, the present inventors have conducted studies on the sex pheromone of the cotton moth, extracting components having an attractive property to males from the female adult of the cotton moth, and furthermore, these chemically synthesized compounds It has been found that it has an effective attracting effect on males of the cotton helicopter, Cyperus terrestris. The present invention has been completed based on these findings.

[0004]

DISCLOSURE OF THE INVENTION The present invention relates to the sex attraction of cotton helicopter, which comprises (E) -11-hexadecenal and (E, E) -10,12-hexadecadienal as active ingredients. The agent is provided. less than,
The present invention will be described in detail. (E) -11-hexadecenal and (E, E) -10,1 which are the active ingredients of the present invention.
The mixture with 2-hexadecadienal has a strong sexual attraction effect on males of the cotton helicopter, Poa annua. These active ingredients may be used as such or dissolved in an organic solvent such as hexane to form a solution, which may be adsorbed on a suitable carrier, for example, plastic or rubber such as polyethylene, or encapsulated in a plastic capsule or capillary. According to the method described above, a sustained release preparation characterized by gradually releasing into the air can be obtained. Further, since both compounds have a chemical structure that is susceptible to isomerization by air oxidation and ultraviolet light, the effective period can be extended by adding one or both of an antioxidant and an ultraviolet absorber. Next, the isolation and identification of the active ingredient substance of the present invention and the biological activity test results thereof will be described in detail with reference to examples, but the present invention is not limited to these examples.

[0005]

【Example】

1) Isolation and Identification of Active Ingredient Substance The tracking of the active substance was performed by an assay method using a gas chromatograph equipped with a tactile potential detector utilizing a biopotential generated in a male antenna when an active substance was detected. Cotton larvae were collected in Okinawa Prefecture, and adults were evolved from pupae obtained by breeding using cucumber leaves. Sex pheromone secretory glands near the abdominal terminal node of a total of 57 female adults were cut out and extracted with hexane for 5 to 30 minutes. The extract was fractionated by column chromatography packed with florisil. Analysis of this 5% -ether / hexane fraction using a gas chromatograph equipped with an antennal potential detector revealed that there were two components that produced a clear electrical potential in the antennae of the cotton helicopter male. When the same fraction was analyzed using a gas chromatograph-directed mass spectrometer (GC-MS), the active component was identified as having 16 carbon atoms and 1 and 2 double bonds, respectively, from the obtained mass spectrum. Saturated aliphatic aldehyde (hereinafter referred to as active ingredient A)
And active ingredient B). The mass spectra of both active ingredients are shown in FIGS.

In order to determine the double bond position of active ingredient A, sodium borohydride is added in an alcohol solution to reduce to the alcohol and then acetic anhydride in pyridine to lead to the corresponding acetate, Dimethyl
The derivative was induced to a disulfide adduct and subjected to GC-MS analysis. As a result, the molecular ion becomes m / z 376 (28%).
In addition, characteristic fragment ions each have m / z 2
59 ([CH ₃ COO (CH ₂ ) ₁₀ CHSCH ₃ ] ⁺ , 100
%) And m / z 117 ([CH ₃ SCH (CH ₂ ) ₃ CH ₃ ] ⁺ ,
28%). Therefore, active ingredient A
Was determined to be at the 11-position. Then, when each of the separately synthesized geometric isomers of 11-hexadecenal was compared with natural products by gas chromatography analysis,
The retention time of active ingredient A was consistent with the (E) -isomer. The mass spectrum of the active ingredient A was synthesized (E) -11-
It was also confirmed that it coincided with that of hexadecenal. Based on the above findings, the active ingredient A was identified as (E) -11-hexadecenal.

The mass spectrum of active ingredient B was determined by Ando et a
l. (1988) [Agricultural and Biological Chemistry
Vol. 52, No. 6, pp. 1415-1423] shows that this component has double bonds at the 10-position and 12-position, respectively, that is, the active component has 10,12-hexadecadienal and Estimated. Therefore, 4,12-hexadecadienal, which was chemically synthesized according to a conventional method, was prepared.
Gas chromatographic analysis of the various isomers revealed that the retention time of active ingredient B was consistent with the (E, E) -isomer. The mass spectrum of the active ingredient B is (E, E) -10,1.
It was consistent with that of 2-hexadecadienal. Based on the above findings, the active ingredient was identified as (E, E) -10,12-hexadecadienal.

2) Test of biological activity of active ingredient substance The attracting activity of the synthetic compound against male adult of cotton helicopter was measured in a local field in Okinawa Prefecture. A predetermined amount of each of the synthetic compounds was attached to an insect trap using an adhesive plate as an attraction source, with a rubber piece of 10 mm in diameter and 19 mm in height having a recess of 6 mm in diameter and 8 mm in depth at one end, and cultivation of cucurbits They were suspended in a field and the number of male adults caught was investigated. As a result, it was confirmed that each of the synthetic compounds exhibited the attracting activity even though the generation at the site was extremely low. Furthermore, it was recognized that the use of both compounds significantly increased the attracting activity (Table 1).

[0009]

[Table 1] Table 1 Attraction of cotton helicopter males in a local field, 1996 Amount of component per mg of Okinawa main island rubber cap (mg) Average number of traps per trap per night Component A Component B September 25-27 Date November 21-24 1.00 0.30 0.90 0.10 0.5 1.0 0.67 0.33 1.7 1.8 0.33 0.67 0.8 0.8. 3 0.10 0.90 0 0.2 0 1.00 0.2 0 0 0 0 0 virgin female three animals 14.2 5.0

According to the present invention, two substances ((E) -11-hexadecenal and (E,
E) -10,12-Hexadecadienal) was isolated and identified, and it was found that the combined use of these two substances significantly increased the sexual attraction activity. Therefore, the sex attractant of the present invention is useful for controlling and controlling the occurrence of cotton heliconia hornworm.

[Brief description of the drawings]

FIG. 1 is a mass spectrum diagram of active ingredient A.

FIG. 2 is a mass spectrum diagram of active ingredient B.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Junji Akino 1-2 Owashi, Tsukuba, Ibaraki Pref. Ministry of Agriculture, Forestry and Fisheries, Research Institute for Silk and Insect Agriculture (72) Inventor Norio Aragaki 4-Shurizakiyamacho, Naha City, Okinawa Prefecture 222 Okinawa Agricultural Experiment Station (72) Inventor Irie Kaneshiro 4-222 Shurizakiyamacho, Naha City, Okinawa Prefecture

Claims (1)

[Claims] 1. A sex attractant for cotton helicromeme, characterized by containing (E) -11-hexadecenal and (E, E) -10,12-hexadecadienal as active ingredients.