JP2775304B2 - Insect attractant containing trans-2, cis-13-octadecadienal as an active ingredient - Google Patents

Description

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

Iga (Tinea pellionella) larvae are not only house pests that use protein-containing substances as nutrients but also damage clothing products using wool and silk, and are also warehouse pests that cause great damage to protein foods.

The amount of damage to a single larva is small, but once the clothing is damaged, even if there is no problem in quantity, the effect on the quality is extremely large. 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.

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 secrete compounds having a species-specific attracting effect in order to mate with male adults of the same species. This sex attractant,
That is, by elucidating the chemical structure of the sex pheromone and using the same substance obtained by chemical synthesis, the occurrence status of the pest can be efficiently investigated.

In addition, it is possible to efficiently control pests at the adult stage by using the substance to attract males, disrupt chemical communication between males and females during mating behavior, and the like.

In view of the general background described above, the present inventors (et al.) Have studied a male attractant of adult moth, and have the following chemical formula (I): CH ₃ (CH ₂ ) ₃ CH = CH (CH _{2 9} ) CH = CHCHO (I) The trans-2, cis-13-octadecadienal represented by the formula (I) was found to exhibit a sex pheromone-like attracting effect on adult males of the moth, thus completing the present invention.

Trans-2, cis-13-octadecadienal represented by the chemical formula (I) is a liquid having a refractive index of 1.4656 (25.0 ° C.) and can be used in organic solvents such as n-hexane, ether, acetone, and ethanol. It is soluble and insoluble in water.

Its infrared absorption spectrum is 1696 cm based on the stretching of the aldehyde carbonyl conjugated to the trans double bond.
An absorption of ^-1 is seen.

Proton nuclear magnetic resonance spectra show C-12,13 protons (cis-13) at 5.29-5.49 ppm multiplet and C-2,3 protons (trans-2) at 6.15 ppm and 6.90 ppm double triplet. ), The proton of the aldehyde is observed in the double line at 9.57 ppm.

The mass spectrum was m / z 264 (M ⁺ ) 246 (M ⁺ -1
8) is observed, and the following m / z 109,81 etc. are observed.

This compound can be synthesized by any of several methods, but can be generally synthesized by the following method.

When compound (I) is used as an attractant for imo,
It can be carried out according to other forms of sex pheromone use. That is, since this compound is a liquid having a relatively low vapor pressure, a compound to which an appropriate dispersant has been added is directly used,
Various methods are possible, such as dissolving in an appropriate solvent such as methylene chloride and impregnating it with an appropriate carrier, or using it as it is or in a container and adjusting the volatilization amount.

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

Since compound (I) is relatively susceptible to oxidation, stabilize the compound by using it in the presence of a suitable antioxidant, for example, 2,6-di-tert-butyl-4-methylphenol. Can be.

The method of attraction includes, for example, placing the above-mentioned attraction source containing the active ingredient (I) on an object coated with an appropriate adhesive substance, or in the vicinity thereof, or hanging it on a container containing an appropriate liquid. Attracted adult males of Iga are killed by being trapped in the sticky substance or the container liquid.

Example Synthesis of trans-2, cis-13-octadecadienal (I) 1.00 g of cis-11-hexadecenal (II) was added to benzene 1
The solution was dissolved in 5 ml, 3.53 g of formylmethylenetriphenylphosphorane was added at room temperature, and the mixture was stirred at 70 ° C. for 2 days. Gas chromatography (Hitachi 163, OV-17,5% chromosorb W 1
After confirming the disappearance of the starting aldehyde (II) at m, N ₂ , 1.65 atm), benzene was distilled off under reduced pressure. The n-hexane (20 ml) -soluble portion of the reaction mixture was subjected to silica gel (Kieselgel 60,230-
The mixture was eluted with n-hexane (50): ether (1) and column fractions of trans-2, cis-13-octadecadienal (I) were collected by column chromatography using a 400mesh).
mg liquid was obtained.

Test Example 1 trans-2, cis-13-octadecadienal (I)
4.98 mg was made into a 5 ml solution with n-hexane, and 0.5 μl of the solution was attached to a piece of filter paper (No. 2, 2) (0.5 cm × 0.7 cm) using a hand micro applicator to prepare an attraction test paper. One adult male of Iga 2-4 days after emergence was placed in a 30 ml Erlenmeyer flask and 20 sections were prepared. Subsequently, when the invitation 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 the same experiment was performed using a test paper to which only 0.5 μl of n-hexane was added, a male adult of Iga showed no reaction at all.

Test Example 2 trans-2, cis-13-octadecadienal (I)
4.98 mg was made into a 5 ml solution with n-hexane, and 10 μl of the solution was attached to the center of a piece of filter paper (No. 2, 2 cm) (1.5 cm × 12 cm) using a hand micro applicator, and this was folded in half. The one that came about 5 cm from the bottom was used as the attracting test paper.

Ten males of adult Iga were placed in a glass container 12 cm in diameter and 9 cm in height and 2 to 4 days after emergence, and the tops were covered with tetron gauze, and A and B2 sections were prepared. When the invitation test paper is gently put into this, it immediately shows a search action and is attracted to the filter paper. The number of male attractants of adult Iga reached 7 in the A section and 6 in the B section, and the rest showed active searching behavior.

On the other hand, in a control experiment in which only n-hexane was added under the same conditions, the adult male of Iga did not show any searching behavior and was not attracted to the filter paper at all.

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

From the above results, it was found that trans-2, cis-13-octadecadienal was a substance having an extremely small amount (0.498 × 10 ⁻³ mg) and a remarkable attracting activity to adult males of Iga.

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Claims (1)

(57) [Claims] 1. The trans-2, cis-13-octadecadienal represented by the chemical formula (I): CH ₃ (CH ₂ ) ₃ CH = CH (CH ₂ ) ₉ CH = CHCHO (I) Attractant for Iga, comprising as an active ingredient.