JPH08295602A - Sweet potato leaf worm attracting agent - Google Patents

Abstract

PURPOSE: To obtain a sweet potato leaf worm (Aedia leucomelas) attracting agent by utilizing the sex pheromone of female imagoes of sweet potato leaf worm which is an important insect pest to sweet potatoes. CONSTITUTION: This sweet potato leaf worm attracting agent contains (Z,Z, Z)-3,6,9-heneicosatriene as an active ingredient. Since this compound is remarkably effective with an extremely small amount, and is volatile, it is preferable to use the compound by adsorbing to a suitable carrier (various synthetic polymers, natural rubber and synthetic rubber) or sealing in the molded materials of these carriers. As to the content of the active ingredient in the case of adsorbing to the carrier or sealing in the molded materials of these carriers, approximately 0.1-100mg per 1g is desirable. This active ingredient is obtained by using a natural linoleic acid as a raw material and by its reactions with (1) diazomethane, (2) lithium aluminum hydride and p-toluene sulfonic acid chloride, and (3) diisopropylcopperlithium.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an attractant for Nakajiro citaba.

[0002]

2. Description of the Related Art Acacia leucata (Aedia leuc)
omelas lin) is an important insect pest of sweet potato. This pest damages the leaves of sweet potato and bites the leaves when the density increases. Therefore, pesticide control is usually performed, but from the standpoint of preventing environmental pollution, there is a demand for a method for controlling Nakajiroshitaba, which does not depend on pesticide control.

[0003]

Recently, the chemical structure of so-called sex pheromones has been clarified for many pests, and the use of this attractive sex pheromone has made it possible to efficiently carry out investigations on the developmental frequency of pests. It was The sex pheromone is a chemical substance generally secreted by female adults and has a species-specific attraction to male adults of the same species. By clarifying the chemical structure of such an attractive sex pheromone, chemically synthesizing this substance and using it as a so-called sex attractant,
It is possible to efficiently investigate the occurrence and prevalence. Furthermore, by using this sex attractant, a large amount of males can be killed or the mating behavior of males and females can be disturbed to control pests in the adult stage. In view of these circumstances, the present inventors have conducted a study on the sex attractant of Nakajiro Sitaba, extracted a component having attracting activity to males from virgin females of Nakajiro Sitaba, and determined its chemical structure. Furthermore, it was found that the chemically synthesized compound has an effective attracting effect on Nakajiroshitaba. The present invention has been completed based on these findings. The active ingredient of the attractant of the present invention is 3,6,9-heneicosatriene and all three double bonds are in the cis configuration, ie (Z, Z, Z) -3,6. , 9-henei cosatriene.

When the compound of the present invention is used as an attractant, various usage forms are possible. Since these compounds are extremely effective in a very small amount and are volatile, they can be adsorbed on an appropriate carrier (various synthetic polymers, natural rubber, synthetic rubber, etc.) or molded into these carrier materials. It is preferably used in the form of being enclosed in a product.

The content of the active ingredient can be appropriately determined, but when it is adsorbed on a carrier or enclosed in a molded carrier material, it is preferably about 0.1 to 100 mg per 1 g of the carrier.

A carrier or carrier material molded product containing such an active ingredient is supported by a suitable support, for example, on a container containing water or other liquid, or on an object coated with a suitable adhesive substance, or the same. When installed in the vicinity, the attracted Nakajiroshitaba drops into the container or is trapped by an adhesive substance and dies.

The present invention will be described in detail below step by step.
In order to elucidate the chemical structure of the sex attractant of Nakajiroshitaba, we first extracted the components with attractant activity from virgin females. The presence or absence of activity was determined by an electrophysiological method using the antenna of male adults. It was judged that a potential difference of several mV was generated when the sample was sprayed on the antenna when it was active.

About 600 virgin female hexane extracts were concentrated, dehydrated and fractionated by column chromatography using a column packed with silica gel. Elution starts with 15
0 ml hexane, then 150 ml 5% ether /
Performed in hexane, the active fraction was in the hexane eluate.
This active fraction was further fractionated by silica gel column chromatography impregnated with silver nitrate. Elution is initially 150 ml
Hexane, then 1%, 3%, 5%, 10 of each equal volume
% And 25% ether / hexane for stepwise elution, the active fraction was in 5% ether / hexane.

In the mass spectrum of the component thus purified, a large fragment peak was detected at 234 (M-56) and 108 with M ⁺ of 290. In order to determine the position of the double bond, it was partially reduced with aqueous hydrogen peroxide and human razine. In addition, epoxidation and ozone decomposition were performed. The retention time of the partially reduced product was compared with that of monoene synthesized using a capillary column (ss-4). From these measurements, the positions of double bonds were 3, 6, and 9, and their geometric structures were all assumed to be cis.

Since a substance having this putative structure was synthesized and a strong attracting activity was confirmed in the field, the sex attractant of Nakajiroshitaba is (Z, Z, Z) -3,6,9-heneicosatriene. It was confirmed. This compound is Co
nner, W.N. E. FIG. Etc. "Sex attracta
nt of an Arctic moth (Ute
theisa ornatrix): A pulsed
chemicalsignal. Behav. Eco
l. Scociobiol. , 7: 55-69 (1
980), but the document does not disclose any attractant activity of the compound against Nakajirocitaba.

The active ingredient compound of the present invention is (1) reacted with diazomethane from a natural linolenic acid as a raw material,
It can be easily synthesized by sequentially performing (2) a reaction with lithium aluminum hydride and p-toluenesulfonic acid chloride and (3) a reaction with diisopropyl copper lithium.

Test Example 1 The attraction activity of the active ingredient of the present invention obtained by synthesis was confirmed by an attraction test in the field. The test was conducted as follows. Rubber septa were impregnated with 0.1 to 3 mg of compound. This was hung on a basin containing soapy water, and the number of insects killed was investigated every day. A net basket containing a virgin female was used as a trap. The results are shown in Table 1. Test location Kushira Town, Kagoshima Prefecture

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Gen Sugie 2-23-17 Higashi Tsukuba, Ibaraki Prefecture (72) Inventor Yukio Ando 2-9 9 Kotobuki, Kagoshima Prefecture Asami Yamashita Kagoshima Prefecture 4741 Hosoyamada, Kushira-cho, Hashimoto-gun (72) Inventor Shingo Oya 5-3, Honjo-cho, Joetsu City, Niigata 102 (72) Inventor Hidemi Kamiwada 1218, Kamifukumoto-cho, Kagoshima City, Kagoshima Prefecture (72) Inventor Hiroshi Suzuki 3-7-3 Nakamon-cho, Joetsu City, Niigata Prefecture 38 (72) Inventor Takehiko Fukumoto 5-40-301 Sanai Town, Joetsu City, Niigata Prefecture

Claims (1)

[Claims] 1. An attractant for Nakajiro citaba containing (Z, Z, Z) -3,6,9-heneicosatriene as an active ingredient.