JP2739652B2 - Insect attractant containing trans-2-octadesenal as an active ingredient - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a moth attractant.

Iga (Tinea pellionella) is a house insect pest that uses protein-containing substances as a nutrient source and damages clothing products using wool and silk, and is also a warehouse insect that causes a great deal of damage to protein foods.

Once the larva is eaten, garments are irreparably damaged and lose commercial value. The situation is exactly the same for food.

Since many pests are required to be highly safe, such as clothing and food, which contact the human body, the control agents that can be used are also limited.

Further, although the number of occurrences of imo is one or two times per year, it is difficult to specify the time of occurrence because the climate differs depending on the living area. Therefore, its control is also difficult.

Recently, studies on sex pheromones of pests have been actively conducted from the viewpoint of comprehensive control of pests, and the occurrence and fate of considerable pests have been efficiently grasped by using these sex pheromones. In general, female adults
Secretes a compound having a species-specific attracting effect in order to mate with the same adult male. By elucidating the chemical structure of the sex attractant, that is, the sex pheromone, and utilizing the same substance obtained by chemical synthesis, the occurrence status of the pest can be efficiently investigated.

In addition, by using the substance to induce males and disrupt mating, it is possible to efficiently control pests at the adult stage.

The present inventors have studied the female sex pheromone of the adult Iga female in consideration of the general background described above, and have the following chemical formula (I): CH ₃ (CH ₂ ) ₁₄ CH = CHCHO. Trans-octadecenal represented by I) was found to exhibit an effective attracting effect on adult males of Iga, thereby completing the present invention.

Trans-2-octadecenal represented by the chemical formula (I) is a crystal having a melting point of 44 to 46 ° C., and is composed of n-hexane,
A compound that is soluble in organic solvents such as ether, acetone, and ethanol, and insoluble in water.

Its infrared absorption spectrum was 1688 cm based on the stretching of the aldehyde carbonyl conjugated to the trans double bond.
Absorption is seen.

The proton nuclear magnetic resonance spectrum shows a proton at C-18 at 0.89 ppm with a triplet and a C-4 to C-1 at 1.28 ppm with a multiplet.
7 protons, C-3 proton at 2.33 ppm double triplet, 6.10 ppm C-2 proton at double triplet at 6.10 ppm
The proton of C-3 is observed in the double triplet, and the proton of the aldehyde is observed in the doublet at 9.55 ppm.

Mass spectrometry spectra were m / z 266 (M ⁺ ), 248 (M ⁺ −1
8), 237 (M ⁺ -29), 222 (M ⁺ -44), 111 (M ⁺ -155)
And m / z 96, 83, 70, etc. are observed below.

This compound can be synthesized by several methods, but can be synthesized by the following method as a general method.

When compound (I) is used as an attractant for imo,
It can be carried out according to the use form of other sex pheromone. That is, since this compound is a crystal having a relatively low vapor pressure, a compound to which an appropriate dispersing agent has been added is directly used or dissolved in an appropriate solvent such as methylene chloride and then impregnated with an appropriate carrier. Can be used as it is or in a container and the volatilization amount is adjusted and used.

It is desirable that the concentration of the compound (I) contained in the carrier is appropriately determined depending on the type of the carrier material and the conditions of use.

Since compound (I) is relatively susceptible to oxidation, its stabilization can be improved by using it in the presence of an appropriate antioxidant, for example, 2,6-di-tert-butyl-4-methylphenol. Can be planned.

As a method of attraction, the above-mentioned attraction source containing the active ingredient (I) is placed on an object coated with a suitable adhesive substance, or
It may be placed nearby or hung on a container containing an appropriate liquid, and the male of the adult moth immature that is attracted in this way will be trapped in the sticky substance or the liquid of the container and die. .

Example Synthesis method of trans-2-octadesenal (I) Synthesis of hexadecanal (III) 1.8 g of chromic anhydride (CrO ₃ ) was gradually added to 30 ml of pyridine while stirring to obtain a yellow-brown slightly viscous solution. , This one
-A solution of 5.0 g of hexadecanol (II) in pyridine (20 ml) was added with stirring at room temperature. After stirring for 3.5 hours, the mixture was poured into water, extracted twice with ether, dried over anhydrous magnesium sulfate, separated by filtration, and concentrated. The obtained n-hexane solution was purified with 150 ml of silica gel (Kieselgel 60, 230 to 400 mesh). Hexadecanal (III) eluted with n-hexane
2.00 g (mp 36-38 ° C.) were obtained.

Synthesis of trans-2-octadecene-1-ol (V) 2.00 g of hexadecanal (III) was dissolved in 20 ml of benzene, and a solution of 3.28 g of methoxycarbonylmethylenetriphenylphosphorane in 20 ml of benzene was stirred at room temperature at room temperature. In addition, it was left for a day. Gas chromatography (Hitachi 163, OV-1
After confirming that the raw material aldehyde (III) (retention time: 1.65 minutes) has disappeared at 7,5% chromosorb W 1m, N ₂ , 1.65 atm), the condensate (IV) ( The purified product (mp 34-36 ° C) was dissolved in 30 ml of ether. To a suspension of 380 mg of lithium aluminum hydride in 40 ml of ether was added a solution of 460 mg of ethanol in 5 ml of ether, and the ether solution of the condensate (IV) obtained above was added dropwise at room temperature with stirring. Stirring was continued until the ester condensate disappeared (about 1.
00 hours). Pour the reaction solution into water and extract with ether (3 times)
The extract was dried (MgSO ₄ ), separated by filtration and concentrated to obtain 3.7 g of a reduced composition. 1.8 g of n-hexane soluble part
Purified in 150 ml. n-hexane, n-hexane (9
9): Eluted sequentially with ether (1), n-hexane (98): ether (2). The fraction of 2-octadecene-1-ol (V) was collected and 334 mg of crystals (mp 47-47.5
° C).

Synthesis of trans-2-octadesenal (I) Trans-2-octadecene-1-ol (V) 320 m
g was dissolved in 5 ml of pyridine.
g) in a mixture of pyridine (10 ml) at room temperature and stirred for about 60 minutes. Pour the reaction solution into water and extract with ether (3 times)
Then, it was washed with water, a 5% hydrochloric acid aqueous solution and water. Dry (MgS
O ₄ ), filtered and concentrated to give 315 mg of crystal (I) having a melting point of 44 to 46 ° C.
I got

Test Example 1 5.0 ml of trans-2-octadesenal was made into a 5 ml solution with n-hexane, and 0.5 μ of the solution was attached to a piece of filter paper (No. 2) (0.5 cm × 0.7 cm) using a hand micro applicator. Was prepared.

Twenty male iga adults were placed in a 30 ml Erlenmeyer flask 2 to 4 days after emergence. Subsequently, when the test papers were gently placed in them, 18 of the 20 plots were immediately attracted to the test strips, and 2 plots showed active searching behavior.

On the other hand, when a similar experiment was carried out using test paper to which only 0.5 μm of n-hexane was added, male Iga adults did not show any reaction.

Test Example 2 5.05 mg of trans-2-octadesenal was made into a 5 ml solution with n-hexane, and 10 μ of the solution was attached to a piece of filter paper (No. 2) (1.5 cm × 2 cm) using a hand micro applicator.
This was placed almost at the center of the adhesive plate (2 cm x 5 cm) to make an attractive adhesive plate. A glass container with a diameter of 12 cm and a height of 9 cm covered with tetron gauze was prepared in two sections, A and B, and 10 males each of the Iga adults 2 to 4 days after eclosion were added thereto. 2 cm from the bottom of each of the above attracting adhesive plates
When placed in the position, the adult Iga male immediately showed an exploratory behavior, and was gradually attracted to and adhered to the adhesive plate. After 10 minutes, the number of males attached to the adult Iga reached 8 in both A and B2 groups, and the remaining 2
The animals showed only exploratory behavior.

On the other hand, in a control experiment in which only n-hexane was added under the same conditions, no adult male of Iga showed any seeking behavior and was not attracted to the adhesive plate at all.

Test Examples 1 and 2 were conducted at room temperature of 20 to 22 ° C.

From the above results, it was found that trans-2-octadesenal was a substance having an extremely small amount (0.505 × 10 ⁻³ mg) and a remarkable attraction activity to adult males of Iga.

Claims (1)

(57) [Claims] 1. An attractant for Iga containing trans-2-octadecenal as an active ingredient represented by the following chemical formula (I): CH ₃ (CH ₂ ) ₁₄ CH = CHCHO (I)