JPH0365337B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel verbanol compound and a cockroach attractant containing the compound as an active ingredient.

Cockroaches are global sanitary pests and are distributed throughout Japan. As a way to get rid of cockroaches,
A known method is to place an exterminator in the path of cockroaches and trap them. In this method, a cockroach attractant is often placed inside the exterminator. As a cockroach attractant, sex pheromones are known to attract males, and T-casinol is known to co-excite males and females.

The present inventors, while searching for substances that have a cockroach-attracting effect, discovered that a certain type of novel berbanol-based compound has an extremely excellent attracting effect, and achieved the present invention.

That is, the gist of the first invention resides in (+)-vervanyl methyl carbonate, and the gist of the second invention resides in a cockroach attractant containing the compound as an active ingredient.

To explain the present invention in detail, (+)-berbanyl methyl carbonate, which is a novel berbanol compound of the present invention, is prepared by dissolving (+)-berbanol in a suitable solvent and producing chloroformic acid as shown in the formula below. It can be obtained by reacting with methyl.

In addition, (+)-berbanol in the above formula (1) is
Agricultural Biological Chemistry, 43 , 1967
~1974 (1979).

The (+)-vervanyl methyl carbonate of the present invention represented by the above formula (2) is a compound that has not been described in any literature, and its structure was confirmed from the analysis results in the Examples below.

The compound of the present invention is suitable as an attractant because it excites male cockroaches, attracts them from their hiding places, and induces behavior similar to sex pheromones around the compound, as shown in the test examples below. The amount used as a cockroach attractant is only about 0.5 μg, and its action is significantly superior to that of known similar compounds. This agent is usually used by placing it on the capture surface of a cockroach exterminator, such as a surface coated with an adhesive substance.

Hereinafter, the present invention will be explained in more detail with reference to production examples and test examples, but the present invention is not limited to these examples.

Production example: 50mg of (+)-berbanol shown by the above formula (1)
(0.325 mmol) in 0.1 ml of anhydrous pyridine (solvent) and cooled on ice. Add to this 0.025 methyl chloroformate
ml, stirred for 10 minutes, and further stirred at 50°C for 3 hours to react. After the reaction solution was allowed to cool, 5 ml of ice water was added, and then extracted with ether (three times of 10 ml). Separate the ether layer and add 8 ml of 1N-
After washing successively with HCl and 5 ml of a saturated aqueous sodium bicarbonate solution, the mixture was dried by adding anhydrous magnesium sulfate and concentrated under reduced pressure.

The oil thus obtained was purified by silica gel chromatography (using 10 g of silica gel, developed with hexane-ethyl acetate (20:1)) to give the (+)-bervanyl compound represented by the formula (2) above. 49.6 mg (0.234 mmol, yield 72%) of methyl carbonate was obtained.

Specific rotation of this product [α] ²⁵ _D : +8.3° (C=1.00, n
-hexane); gas chromatograph GC (3% OV
−225, column size 0.3×200cm, column temperature 110
°C, _N2 flow rate 40 ml/min): retention time (tR) 25.7 min;
Mass spectrum MSm/e: 212 (M ⁺ ), 197 (M ⁺ −
15), 181 (M ⁺ −31), 157, 156, 153 (M ⁺ −59,
COOCH ₃ ), 143, 136 (M ⁺ −76, HOCOOCH ₃ ),
121 (M ⁺ −76−15, reference peak), 107, 99, 93,
81, 69, 67, 55, 43; Infrared absorption spectrum IR
(Film on NaCl plate): 1745, 1270cm ^-1 ; ¹ H−
NMR (CDCl ₃ , 60MHz): 0.86 (3H, s), 0.93
(3H, d, J=6Hz), 1.26 (3H, s), 1.36 (1H,
d, J=9.5Hz, 7-Ha), 3.76 (3H, s), 5.03
(1H, br.t, J=7.5Hz).

Test Example Twenty-five adult male American cockroaches were isolated and reared in a breeding box equipped with a shelter in which seven sheets of paper were placed at regular intervals, and this was used for a physiological activity test.

A solution of 0.5 μg of (+)-vervanyl methyl carbonate obtained in the production example dissolved in n-hexane was absorbed onto a piece of paper measuring 2.5 cm long and 0.5 cm wide. After the solvent was evaporated at room temperature, the breeding box was placed. The animals were placed in a cage and gently placed 4 cm from the shelter and 3 cm from the side wall of the rearing box.

Within 3 minutes after placing the paper on the paper, it started to exhibit characteristic sexual behavior (starting running from the shelter, moving violently around the paper, raising its wings and vibrating violently, and attempting to mate by protruding the copulatory organ in its tail). Count the number of heads. As a result of five trials, the average number of animals that engaged in sexual behavior was 10 out of 25. All tests were conducted in dim light, and
The breeding boxes that were once subjected to the test were not used for several days.

Claims (1)

[Claims] 1 (+)-Vervanyl methyl carbonate. 2. A cockroach attractant containing (+)-bervanyl methyl carbonate as an active ingredient.