JPH0625279A - Cockroach-collecting pheromone, and cockroach control agent containing cockroach-collecting pheromone - Google Patents

Abstract

PURPOSE:To provide a cockroach-collecting pheromone comprising a cockroach- attracting substance and a cockroach-restraining substance and useful as a cockroach-controlling agent extremely excellent in its controlling effect because of having both the attracting activity and the rest-raining activity against cockroaches. CONSTITUTION:The cockroach-collecting pheromone comprises a cockroach- attracting substance (e.g. ammonia, methylamine) and a cockroach-restraining substance of the formula (R1 is a sugar component beta-bonded to the steroid skeleton; R2 is 1-12C linear or branched alkyl; X is H, halogen; Y, Z are H, hydroxy). The compound is, e.g. 1-(6alpha-chloro-4beta,5beta-epoxy-5beta-stigmasteron-3beta-yl)-beta- D-glucopyranoside.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a cockroach-aggregating pheromone and a cockroach-controlling agent containing the cockroach-aggregating pheromone.

[0002]

BACKGROUND ART Cockroaches are typical sanitary pests,
It invades not only ordinary households but also various industrial places and causes serious damage. Therefore, many extermination methods are used, but since the habitat is closely related to human life, the use of pesticides is limited, and the habit of concealing in narrow gaps and the fertility are strong, so conventional insect repellents are used. The current situation is that effective disinfection has not been obtained with vessels and food poisons. recent years,
Research on the pheromone of cockroaches has progressed, and its use for control has begun to be considered. Pheromones are chemical substances secreted by insects themselves for the preservation of species, and are known to exhibit a strong activity such as a strong attraction in a very small amount. Therefore, if it is used as an attractant in insect traps and food poisons, it is expected that the extermination effect can be enhanced. However, attractants known so far, for example, periplanones, bornyl acetate, terpenoids, etc., have poor sustainability of the effects and can sometimes be changed to the opposite repellent factor, so that it is practically sufficient. It was not there.

[0003]

In view of the above situation, the present inventors have aimed to search for a useful cockroach attracting substance,
The filter paper shelters contaminated with the German cockroach excretion were investigated, and after extraction and purification, alkylamines were isolated as substances showing high attracting activity. However, the alkylamines alone have a problem that the attracting action remains transient and the cockroaches cannot be settled in the attracting source. That is, it was necessary to obtain a so-called aggregated pheromone-like substance in which restraint activity was added to attracting activity in order to apply it to a cockroach repellent.

[0004]

As a result of further intensive studies, the inventors of the present invention have found that the steroid glycoside represented by the formula I acts as a cockroach restraining substance, and is associated in association with the attractant. The inventors have found that a pheromone constitutes and have completed the present invention. That is, the present invention provides a cockroach attractant and a compound of formula I

[Chemical 3] (In the formula, R ₁ represents a sugar component that forms a β bond with the steroid skeleton, R ₂ represents a chain or branched alkyl group having 1 to 12 carbon atoms, and X represents a hydrogen atom or a halogen atom. Y and Z are a hydrogen atom or a hydroxy group, and Y and Z may be linked to each other to form an epoxy group.)
The present invention relates to a cockroach-aggregating pheromone consisting of a cockroach-restricting substance represented by and a cockroach repellent containing the same.

[0005]

As the cockroach attracting substance used in the present invention, alkylamines such as ammonia, methylamine, dimethylamine, trimethylamine, diethylamine, isobutylamine and isoamylamine, 2-dimethylaminoethanol, 1-dimethylamino-2- Methyl-
2-propanol, 2-dimethylamino-2-methyl-
Examples thereof include amino alcohols such as 1-propanol, conventional periplanones, bornyl acetate, terpenoids, etc., but are not limited thereto. In addition, since amines generally have high volatility,
It is preferable to form a salt with various organic or inorganic acids to give sustained release. The required amount of the attractant that exerts the attractant activity varies depending on the type of the attractant, the type of target cockroach, the carrier to be retained, and the like. For, for example, German cockroaches, trimethylamine hydrochloride per 1 cm ² of filter paper is used. It may be impregnated with 0.1 nmol or more.

The aggregate pheromone of the present invention is obtained by associating the above-mentioned attractant with the restraining substance represented by the formula I. The substance of formula I is a steroid glycoside, and as the sugar component represented by R ₁ , various monosaccharides, disaccharides and polysaccharides can be used, and examples thereof include glucose, galactose, maltose and lactose. it can. Also, R
₂ represents a chain or branched alkyl group, for example,
A 1-methylbutyl group constituting a cholan steroid skeleton,
Examples include 1,5-dimethylhexyl group constituting a cholestane skeleton, 1,5-dimethyl-4-ethylhexyl group constituting a stigmastane skeleton, and 1,4,5-trimethylhexyl group constituting an ergostan skeleton. You can Steroids occupy a large part in hormones that transmit information between tissues, but it is extremely rare that they are used as pheromones that transmit information between individuals. It is of great significance not only for its usefulness, but also for elucidating the synthetic pathways or action mechanisms of various signaling substances secreted by insects.

The restraint substance disclosed in the present invention is a novel substance,
An example is as follows. There are various optical isomers based on the steric structure of steroids, and any one of them or a mixture thereof is included in the present invention. Restraint substance 1

[Chemical 4] 1- (6α-chloro-4β, 5β-epoxy-5β-stigmastan-3β-yl) -β-D-glucopyranoside El-MS spectrum M ⁺ (aglycone): 46
4.34 (C ₂₉ H ₄₉ O ₂ Cl) ¹³ C-NMR spectrum δc: 56.0 (4
C), 67.6 (5C), 58.5 (6C) Constrained substance 2

[Chemical 5] 1- (6α-chloro-5β-hydroxy-5β-stigmastan-3β-yl) -β-D-glucopyranoside El-MS spectrum M ⁺ (aglycone): 46
6.35 (C ₂₉ H ₅₁ O ₂ Cl) ¹³ C-NMR spectrum δc: 28.8 (4
C), 76.1 (5C), 67.4 (6C) Constrained substance 3

[Chemical 6] 1- (4β-hydroxy-5β-cholestane-3β-yl) -β-galactopyranoside El-MS spectrum M ⁺ (aglycone): 40
_{4.03 (C 27 H 48 O 2} )

The binding substance of the present invention is a liquid or a solid at room temperature and is generally easily dissolved in a polar solvent such as methanol. The amount of restraint activity varies depending on the type of cockroaches and the conditions of use, but for example, when soaked in filter paper, the ED of restraint substance 1 against German cockroaches is used.
₅₀ (median effective dose) is about 2 × 10 ⁻⁴ nmol / c
m ² , while the ED _{50 of} restraint material 2 is about 2 × 10 ^−2.
It was nmol / cm ² .

In the present invention, the cockroach restraining substance is used together with the above-mentioned cockroach attracting substance to form an aggregated pheromone. This compound is extremely effective because it has both an attracting activity and a restraining activity due to the combined action of both substances. Provide a means for exterminating cockroaches. For example, it may be mixed with a food poison containing an insecticide, or may be used in an adhesive trap, powder, granules,
It can be appropriately applied to various cockroach control agents such as aerosol agents, liquid agents and sheets to enhance the control effect.

As the insecticide used in combination, pyrethrin,
Pyrethroids such as allethrin, flamethrin, resmethrin, phenothrin and permethrin, organophosphorus agents such as fenitrothion, trichlorfon and dichlorvos, carbamate agents such as carbaryl and BPMC, boric acid, hydramethylnon, etc., and these are microencapsulated. Alternatively, of course, inclusion with cyclodextrin is acceptable. As the carrier used in preparing the food poison, silicic acid, kaolin, various mineral powders such as talc, wood flour, corn flour, wheat flour,
Examples thereof include various plant powders such as starch, components such as molasses, skim milk powder, fish meal, excipients such as avion, and sticking agents. Examples of the base material used in the sticky insect trap include natural rubber-based materials, or synthetic rubber-based adhesive materials mainly composed of polybutene and polyisobutene and having an increased adhesive strength with rosin, paraffin wax and the like. In addition, if necessary, by appropriately blending components such as fragrances, deodorants, bactericides, or auxiliary components such as stabilizers and solvents, a multipurpose composition with excellent potency can be obtained, which saves labor. Therefore, a synergistic effect between drugs can be expected sufficiently.

When the cockroach pesticide containing the cockroach aggregate pheromone of the present invention thus obtained is applied to a place where cockroaches are discharged, such as in a kitchen, a warehouse or the back of a refrigerator, the attracting effect and restraining effect of the aggregate pheromone are combined. It has a high eradication effect on German cockroaches, American cockroaches and the like.

In order to further clarify that the assembly pheromone provided by the present invention and the cockroach controlling agent containing the same are excellent, the following Test Examples and Examples are shown.

[0013]

[Test Example 1] A filter paper (Whatman No. 1, 2 × 8 cm) containing the sample shown in Table 1 and a control paper filter were each folded into a W shape, and a plastic cup (inner diameter 8 cm, height 4.
5 cm) and placed facing each other. The inside of the cup was dusted with talcum powder to prevent the test insects from escaping. 20 cups were prepared for each sample, and 10 cups of young German cockroach larvae were placed in each cup.
30 heads were released and the number of individuals on the filter paper was recorded 40 minutes later. + When the sample filter paper population exceeds that of the control filter paper
(With restraint activity), in the opposite case- (with repellency), about the same ±
It was evaluated as (no restraint activity). The concentration of the attractant used is a concentration at which sufficient attracting activity was shown in the attraction test by the disc method.

[0014]

[Table 1]

As a result of the test, the aggregated pheromone of the present invention in which the attractant is added to the restraint substance showed a high restraint activity, whereas the attractant alone could not fix the cockroaches, and thus the attractant activity was low. It was shown to be transient. Furthermore, the effect was inferior even with only restricted substances, confirming the usefulness of combining both substances.

[0016]

Example 1 5 parts of microencapsulated fenitrothion, 15 parts of boric acid, 10 parts of skimmed milk powder, 5 parts of sesame oil,
5 parts of starch, 20 parts of rice bran, and 100 ppm of trimethylamine hydrochloride in a mixture composed of other plant-based materials,
Add the binding substance 1 to 1ppm and knead well,
A food poison was prepared. When this food poisoning agent (10 g / 1 cup) was installed in the kitchen at a rate of 1 per 1 m ² , the eating rate of cockroaches was high, and the exterminating effect was superior to that of the conventional borate dango.

[0017]

EXAMPLE 2 95 parts of polybutene (molecular weight 900), 4 parts of polyisobutylene (molecular weight 1.2 million) and 500 p of 2-dimethylamino-2-methyl-1-propanol hydrochloride were added.
pm, restraining substance 2 was added to 5 ppm to prepare an adhesive composition, and the composition was applied to a cardboard having a width of 10 × 15 cm and a thickness of 1 mm to a thickness of 0.5 mm to attract cockroaches. An adhesive plate was obtained. When this and an adhesive plate containing only the attractant were installed in the cafeteria and compared, the former had a high insect trapping rate, and the effect of the association of the attractant and the restraint was confirmed.

[0018]

INDUSTRIAL APPLICABILITY The aggregated pheromone of the present invention has both attracting activity and restraining activity, and when applied to a cockroach controlling agent, it is extremely useful for enhancing the controlling effect.

Claims (2)

[Claims] 1. A cockroach attractant and a compound of the following formula I: (In the formula, R ₁ represents a sugar component that forms a β bond with the steroid skeleton, R ₂ represents a chain or branched alkyl group having 1 to 12 carbon atoms, and X represents a hydrogen atom or a halogen atom. Y and Z are a hydrogen atom or a hydroxy group, and Y and Z may be linked to each other to form an epoxy group.)
Cockroach aggregation pheromone consisting of cockroach restraint material represented by 2. A cockroach attractant and a compound of the following formula I: (In the formula, R ₁ represents a sugar component that forms a β bond with the steroid skeleton, R ₂ represents a chain or branched alkyl group having 1 to 12 carbon atoms, and X represents a hydrogen atom or a halogen atom. Y and Z are a hydrogen atom or a hydroxy group, and Y and Z may be linked to each other to form an epoxy group.)
A cockroach repellent comprising a cockroach aggregation pheromone consisting of a cockroach restraining substance represented by: