JPH07223909A - Sex attractant to tea tussock moth - Google Patents

Abstract

PURPOSE:To obtain a sex attractant having extremely strong attractivity to a male tea tussock moth. CONSTITUTION:This sex attracting agent to a tea tussock moth is composed of 10,14-dimethylpentadecyl isobutylate alone or a mixture of 10,14- dimetylpentadecyl isobutylate with 14-methylpentadecyl isobutylate. Those compounds are isolated from a fraction of an extract of an adult female tea tussock moth having attractiveness to a male tea tussock moth. By adding 14-methylpentadecyl isobutylate, the sex attracting activity of 10,14- dimethylpentadecyl isobutylate is extremely increased. A sex attractant formulation capable of slowly releasing the active components into air is obtained by e.g. impregnating an appropriate carrier (e.g. a rubber and a plastic) with the active components as they are or after dissolved in an organic solvent, e.g. hexane or sealing those active components into a plastic capsule or capillary.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a sex attractant for Chaduga moth, and more specifically, it contains 10,14-dimethylpentadecyl isobutyrate or a mixture of the compound and 14-methylpentadecyl isobutyrate as an active ingredient. It relates to Chadokuga's sex attractant.

[0002]

[Background Art] Chadokuga (Scientific name: Euproctis
Psudoconspersa) feeds on Camellia plants such as tea, camellia, and sasanqua, and larvae of the second and older instars have poisoned hair needles that attach to cocoons and when adults, especially female adults, emerge, abdomen and tail. Damages hair.
In addition, when the poisonous needle touches human skin, it causes inflammation. Therefore, Chadokuga is a pest that eats tea and camellia trees, and is also a hygienic pest for humans. Traditionally, the control of Chadokuga has been done by spraying insecticides, but in order to effectively control Chacoduga, it is necessary to accurately know the time of its occurrence. Development is required.

Recently, the chemical structure of the sex pheromone of many pests has been clarified, and it has become possible to efficiently carry out the investigation of the developmental fate of pests using the attractant sex pheromone. A method for controlling pests by using them to capture a large number of adult males or to disturb the mating behavior of males and females is being developed. In view of such circumstances, the present inventors have conducted diligent research on the sex pheromone of Chaduga moth, and as a result, in an extract having an attractive property to males of Chaduga moth, it is extremely strong in attracting males of Chaduga moth. A substance having an action was found.
The present invention has been completed based on these findings.

[0004]

DISCLOSURE OF THE INVENTION The present invention provides a sex attractant containing 10,14-dimethylpentadecyl isobutyrate as an active ingredient, which has an extremely strong attractant property to males of Chaduga moth, and 10,14-dimethylpentadecyl. The present invention provides a sex attractant for Chadokuga that contains a mixture of isobutyrate and 14-methylpentadecyl isobutyrate as an active ingredient.

The present invention will be described in detail below. It was found that 10,14-dimethylpentadecyl isobutyrate and 14-methylpentadecyl isobutyrate according to the present invention are substances that have a function of generating a clear potential in the antenna of Chadokuga in the assay by the antenna potential detector. Was issued. And, 10,14-dimethylpentadecyl, isobutyrate is a substance having a strong attracting action to males of Chadoguga, and 14-methylpentadecyl isobutyrate is used in combination with 10,14-dimethylpentadecyl isobutyrate. By doing so, it was confirmed that it has the effect of further enhancing the sex-inducing activity of 10,14-dimethylpentadecyl isobutyrate.

To prepare the sex attractant according to the present invention, 1
It can be carried out by using 0,14-dimethylpentadecyl isobutyrate or a mixture of the compound and 14-methylpentadecyl isobutyrate and utilizing the formulation technology applied in the preparation of a sex attractant. . For example, those active ingredients are dissolved in an organic solvent such as hexane to obtain a solution, and the solution is adsorbed on an appropriate carrier, for example, plastic or rubber such as polyethylene, or enclosed in a plastic capsule or thin tube. It is possible to prepare a sex attractant in the form of being gradually released into the air.

The isolation and identification of the component substances of the sex attractant according to the present invention from adult females and the confirmation of the sex attractant activity will be described in detail below.

(1) Isolation and Identification of Active Substance The trace of the active substance is carried out by a bioassay for examining the attractiveness to adult males in the field and the antenna utilizing the biopotential generated when the male antenna senses the active substance in the room. It was based on an assay method using a gas chromatograph equipped with a potential detector.

Adult larvae were obtained from pupae obtained by collecting naturally occurring larvae of Camellia japonica and Sasanqua and maintaining them indoors.
The sex pheromone-secreting glands near the abdominal terminal node of about 400 female adults were cut out and extracted with hexane for 5 to 30 minutes to obtain an extract. The extract was fractionated by column chromatography packed with Florisil. Also, this extract and 5
Analysis of the% -ether / hexane fraction using a gas chromatograph with a tactile potential detector revealed that there were two components that generated a distinct potential in the antenna of the male Chaduga moth. When the 5% -ether / hexane fraction was analyzed using a gas chromatograph direct coupling mass spectrometer (GC-MS), the active ingredient was saturated aliphatic alcohol having 16 and 17 carbon atoms and saturated aliphatic alcohol having 4 carbon atoms. It was shown to be a mixture of fatty acid esters.

[0010] The measured infrared spectrum of both components using a gas chromatograph directly connected infrared spectrometer, the absorption was observed that each indicate the presence of ester groups in the 1753 cm ^-1 and 1750 cm ^-1. The extracted amounts of both components (hereinafter, a small amount component is referred to as B component and a main component is referred to as A component in the order of outflow in gas chromatographic analysis) per virgin female were about 0.6 ng and about 10 ng, respectively. The mass spectra of these two components are shown in FIG. 1 and FIG.
The infrared spectrum is shown in FIGS. 3 and 4, respectively.

The alcohol fraction obtained by hydrolyzing the fraction containing the active ingredient was treated with methanesulfonyl chloride and subjected to gas chromatograph-directed mass spectrometry as a chloride. The chloride derived from the A component was m / z 274 as a molecule. Ion peak, m / z as a characteristic fragment ion
A peak containing a chlorine atom was shown at 189, and a peak containing no chlorine atom was shown at m / z 113. From this result, it was determined that the alcohol having 17 carbon atoms had a methyl side chain at the 10-position and no side chain at the 10-position or lower. Therefore, separately synthesized three types of dimethylpentadecyl isobutyrate having second methyl side chains at the 12th, 13th and 14th positions were analyzed using gas chromatograph direct coupling mass spectrometry and gas chromatograph equipped with an antenna potential detector. When the result was compared with the analysis result of the component A derived from the extract, it was confirmed that the component A coincided with 10,14-dimethylpentadecyl isobutyrate.

The mass spectrum of chloride derived from component B is
A molecular ion peak was shown at m / z 260, and peaks containing chlorine atoms were shown at m / z 245 and 217 as characteristic fragment ions. From this result, it was suggested that the alcohol moiety having 16 carbon atoms of the component B has a methyl side chain only at the 14th position. Therefore, when separately synthesized 1-chloro-14-methylpentadecane was subjected to gas chromatography direct mass spectrometry, it was confirmed that the retention time and the mass spectrum were the same. Furthermore, the separately synthesized 14-methylpentadecyl isobutyrate was subjected to gas chromatograph direct coupling mass spectrometry and gas chromatograph analysis equipped with a feeler potential detector, and the results were compared with the analysis results of the B component derived from the extract. It was confirmed to be a perfect match.

From the above results, the component (natural product) that generates a clear electric potential in the antenna of the male Chacoduga is a main component, A component is 10,14-dimethylpentadecyl isobutyrate, and a minor component, B. The component was determined to be 14-methylpentadecyl isobutyrate.

(2) Confirmation Test of Sex-Attracting Activity of Active Ingredient Next, separately synthesized 10,14-dimethylpentadecyl isobutyrate (substance A) and 14-methylpentadecyl isobutyrate (substance B) were used. The sexual attraction activity against male adults was examined individually or in combination. Each of the single compounds or a mixture thereof was contained in a filter paper, which was attached to a moth trap as an attraction source and set outdoors. The attracted males of Chaduga moth were captured, and the sex attracting activity of each compound was compared by the number of captured males. The male moth trap used here is a sticker plate coated with a sticky substance. The structure is covered by the roof. The results of this sex attraction activity test are shown in Tables 1 to 3.

[0015]

[Table 1]

The results of this test show that the mixture with 10,14-dimethylpentadecyl isobutyrate (substance A) and 14-methylpentadecyl isobutyrate (substance B) has a pronounced activity for bull moths. It was It was also found that their attracting activity far exceeded that of 3 virgin females.

[0017]

[Table 2]

The results of this test show that 10,14 per filter paper
-A suitable amount of dimethylpentadecyl isobutyrate (substance A) was 24 to 80 ng, and the attracting effect was lowered when the amount was less than or equal to the above. Therefore, it was confirmed that an appropriate amount was present to exhibit the attractive effect.

[0019]

[Table 3]

As a result of this test, the attractiveness of 10,14-dimethylpentadecyl isobutyrate (substance A) was 1
It was found to be significantly enhanced by the addition of 4-methylpentadecyl isobutyrate (substance B).

[Brief description of drawings]

FIG. 1 Mass spectrum of component A (EI 70 eV)
Is.

FIG. 2 Mass spectrum of B component (EI 70 eV)
Is.

FIG. 3 is an infrared spectroscopy spectrum (GC-IR) of component A.

FIG. 4 is an infrared spectroscopy spectrum (GC-IR) of component B.

Claims (2)

[Claims] 1. A sex attractant for Chaduga moth, which contains 10,14-dimethylpentadecyl isobutyrate as an active ingredient. 2. A Chaduga moth sex attractant, which comprises a mixture of 10,14-dimethylpentadecyl isobutyrate and 14-methylpentadecyl isobutyrate as an active ingredient.