JP3814657B2 - Uschakogane sex attractant - Google Patents
Uschakogane sex attractant Download PDFInfo
- Publication number
- JP3814657B2 JP3814657B2 JP19161696A JP19161696A JP3814657B2 JP 3814657 B2 JP3814657 B2 JP 3814657B2 JP 19161696 A JP19161696 A JP 19161696A JP 19161696 A JP19161696 A JP 19161696A JP 3814657 B2 JP3814657 B2 JP 3814657B2
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- Prior art keywords
- uschakogane
- sex attractant
- attractant
- quinazolinedione
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Description
【０００１】
【発明の属する技術分野】
【０００２】
本発明は、鞘翅目コガネムシ科に属するウスチャコガネの性誘引剤に関するものであり、詳しくは１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンを活性成分とすることを特徴とするウスチャコガネの性誘引剤に関するものである。
【０００３】
【従来の技術】
【０００４】
鞘翅目コガネムシ科に属するウスチャコガネ（学名Ａｎｏｍａｌａ ｄｉｖｅｒｓａ Ｗａｔｅｒｈｏｕｓｅ）（旧学名：Ｐｈｙｌｌｏｐｅｒｔｈａ ｄｉｖｅｒｓａ Ｗａｔｅｒｈｏｕｓｅ）の幼虫は芝草の苗根を食害し、大きな被害を与えている。
【０００５】
【発明が解決しようとする課題】
【０００６】
このウスチャコガネによる被害を予防ないし防除することは、従来の殺虫剤によっては、非常に困難な状況にある。この様な現状から、この害虫を効果的に防除するために、その発生を的確に知るための予察手段や、従来の殺虫剤とは異なる新しいタイプの防除手段が強く望まれている。
【０００７】
【課題を解決するための手段】
【０００８】
そこで本発明者らはウスチャコガネの性フェロモンの研究を行い、ウスチャコガネの雌成虫が分泌する誘引活性成分の検索を行った。その結果誘引活性な成分の存在をつきとめた。そしてこの成分を使用することにより、ウスチャコガネ雄に対する誘引効果が著しく発現されて実用上有効な誘引作用を示すことを見い出した。本発明はこれら知見に基づいてなされたものである。
【０００９】
本発明は、１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンを活性成分として含有することを特徴とする鞘翅目コガネムシ科に属するウスチャコガネの性誘引剤を提供するものである。
【００１０】
本発明にかかる性誘引剤の活性成分物質である１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオン〔ＩＵＰＡＣ名：１，３−Ｄｉｍｅｔｈｙｌ（１Ｈ，３Ｈ）−ｑｕｉｎａｚｏｌｉｎｅｄｉｏｎｅ（一般名：Ｎ，Ｎ’−Ｄｉｍｅｔｈｙｌｂｅｎｚｏｙｌｅｎｅｕｒｅａ）〕はウスチャコガネの雄成虫に対して強い誘引作用と行動刺激作用を示す。
【００１１】
本発明にかかる性誘引剤を調製するには、１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンを用いて、通常性誘引剤の調製に際し適用されている製剤化技術を利用して行うことができる。例えば、１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンをそのまま、またはジクロロメタン等の有機溶媒に溶液として、この溶液を適当な担体、例えばポリエチレン等のプラスチックやゴム等に吸着させるか、プラスチック製のカプセルや毛細態様に応じた適当な材料あるいは器具を用いて実用的な形態の性誘引剤とすることができる。
【００１２】
【発明の実施の形態】
【００１３】
以下に、本発明にかかる性誘引剤の成分物質の雌成虫からの単離と同定および化学合成品についての性誘引活性の確認について詳細に記述する。
【００１４】
（１）成分物質の同定
【００１５】
成分物質の追跡は、室内において雄成虫に対する誘引性を調べる生物検定法とガスクロマトグラフに直結した生物検出器を用いて、触角が活性物質を受容した時に発生する神経電位の変化を検出する方法によった。
【００１６】
ウスチャコガネの雌成虫を直接エーテルで抽出し、その抽出物を無極性カラムを使ったガスクロマトグラフィー・直結触角電位検出器（ＧＣ−ＥＡＤ）法を用いて活性のある成分を調べたところ、図１に示すように１８．５ｍｉｎのところにＥＡＤ活性なピークが認められた。また極性カラムを使った（ＧＣ−ＥＡＤ）法では、図２に示すように１９ｍｉｎにＥＡＤ活性なピークが認められた。
【００１７】
また、この抽出物を、シリカゲル（Ｗａｋｏｇｅｌ Ｃ−２００）を用いたカラムクロマトグラフィーで分画した。すなわち、ヘキサン、ヘキサン・エーテル（９５：５，９０：１０，８０：２０，７０：３０，６０：４０，５０：５０，４０：６０，３０：７０，２０：８０，１０：９０）、エーテルの順に流した。そして、ヘキサン・エーテル（４０：６０）の画分に、ほとんどの雄が誘引された。
【００１８】
また、ウスチャコガネのメス３００匹分のエーテル抽出物を濃縮後、ＨＰ−５ＭＳカラムを用いて、ガスクロマトグラフ直結質量分析計（ＧＣ−ＭＳ分析）に注入して分析したところ、図３に示すように分子イオンピークが１９０であることが判明した。
【００１９】
さらに、この抽出物を赤外線直結ガスクロマトで分析したところ、図４に示すように２つのアミド基の存在することが判明した。
【００２０】
そして、これらの分析結果からこの誘引物質の化学構造は、図５に示すように１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンであると推定した。
【００２１】
別途化学合成された１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンを、無極性カラムおよび極性カラムを使ったガスクロマトグラフィーで比較したところ、保持時間が活性天然物と一致した。
【００２２】
以上の結果から、鞘翅目コガネムシ科に属するウスチャコガネの雄成虫に対してきわめて高い誘引作用を示す物質（天然物）は、１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンであると決定された。
【００２３】
（２）化学合成物質の性誘引活性の確認試験
【００２４】
化学合成により得られた１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンをガスクロマトグラフィー・直結触角電位検出器（ＧＣ−ＥＡＤ）に付したところ、明確にＥＡＤの応答が記録できた。
【００２５】
【実施例】
【００２６】
以下に、本発明に係る性誘引剤の実施例について説明する。
【００２７】
性フェロモンの誘引剤は、１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンを適量のジクロロメタンに溶解することで、本発明に係る性誘引剤１を調整した。
【００２８】
そして、該性誘引剤（１ｍｇ）を、ゴムセプタムに含浸させることで性誘引剤１１とした。
【００２９】
また、該性誘引剤（１ｍｇ）を、エチレン酢酸ビニールの共重合体からなるペレットに含浸させて性誘引剤１２とした。
【００３０】
【試験例】
【００３１】
本発明区１として、上記実施例で得た誘引剤１１を入れたプラスチック容器を１０個用意した。
【００３２】
本発明区２として、上記実施例で得た誘引剤１２を入れたプラスチック容器を１０個用意した。
【００３３】
対照区として、中に何も入れない空のプラスチック容器を、１０個用意した。
【００３４】
上記で用意した各区の１０個のプラスチック容器を、それぞれ日本たばこ産業株式会社製のプラスチック製捕虫器にセットして、各区について１０個ずつのトラップを用意した。
【００３５】
これらのトラップを用い、静岡県の朝霧カントリークラブに於いて６月３日から６月４日にかけて、同一環境条件下でウスチャコガネの捕虫試験を行い、各区について、雄成虫の１時間あたりの平均捕虫数を求めた。
【００３６】
試験の結果は図６に示すとおりであった。
【００３７】
すなわち、本発明区１の１トラップあたりの平均捕虫数は３７匹／１時間であった。また、本発明区２の１トラップあたりの平均捕虫数は１５３匹／１時間であった。また、対照区の１トラップあたりの平均捕虫数は１．２匹／１時間であった。
【００３８】
上記結果に示すように、本発明区は、ウスチャコガネに対して、強い誘引力を示すことが明らかになった。
【００３９】
以上の試験例の結果を考察すると、本発明に係る誘引剤は鞘翅目コガネムシ科に属するウスチャコガネの雄成虫に対して極めて高い誘引効果を有することが確認された。
【００４０】
【発明の効果】
【００４１】
本発明の性誘引剤によると、ウスチャコガネの雄成虫に対して高い誘引効果を有し、その防除効果に優れている。
【図面の簡単な説明】
【図１】ウスチャコガネの雌成虫の抽出物を、無極性カラムを使ったＧＣ−ＥＡＤ法により分析した結果を示すグラフ
【図２】ウスチャコガネの雌成虫の抽出物を、極性カラムを使ったＧＣ−ＥＡＤ法により分析した結果を示すグラフ
【図３】ウスチャコガネの雌の抽出物を、ＧＣ−ＭＳ分析により分析した結果を示すグラフ
【図４】ウスチャコガネの雌の抽出物を、赤外線直結ガスクロマトにより分析した結果を示すグラフ
【図５】１，３−ジメチル（１Ｈ，３Ｈ）−キナゾリンジオンの化学構造式を示す図
【図６】捕虫試験結果を示すグラフ[0001]
BACKGROUND OF THE INVENTION
[0002]
TECHNICAL FIELD The present invention relates to a sex attractant for euphorbia belonging to the order Coleoptera, and in particular, 1,3-dimethyl (1H, 3H) -quinazolinedione as an active ingredient, It is about.
[0003]
[Prior art]
[0004]
The larvae of the genus Coleoptera (Anomala diversa Waterhouse) (formerly Phylloperperta waterhouse) devour and damage the seedling roots of turfgrass.
[0005]
[Problems to be solved by the invention]
[0006]
It is very difficult to prevent or control the damage caused by the mosquito, depending on the conventional insecticide. From such a current situation, in order to effectively control this pest, a precautionary means for accurately knowing its occurrence and a new type of control means different from conventional insecticides are strongly desired.
[0007]
[Means for Solving the Problems]
[0008]
Therefore, the present inventors conducted research on the sex pheromone of Uschakogane, and searched for the attracting active ingredient secreted by the adult female of Uschakogane. As a result, the presence of an attractive active ingredient was identified. And by using this component, it discovered that the attracting effect with respect to a male mussel was remarkably expressed, and showed the attracting effect effective practically. The present invention has been made based on these findings.
[0009]
The present invention provides a sex attractant for Uschakoga belonging to the order Coleoptera, which contains 1,3-dimethyl (1H, 3H) -quinazolinedione as an active ingredient.
[0010]
1,3-Dimethyl (1H, 3H) -quinazolinedione [IUPAC name: 1,3-Dimethyl (1H, 3H) -quinazolinedione (generic name: N, N ′) which is an active ingredient substance of the sex attractant according to the present invention -Dimethylbenzoyreneurea)] exhibits a strong attracting action and a behavioral stimulating action against adult males of Uschakoga.
[0011]
In order to prepare the sex attractant according to the present invention, 1,3-dimethyl (1H, 3H) -quinazolinedione is used and the formulation technique applied in the preparation of the usual sex attractant is performed. Can do. For example, 1,3-dimethyl (1H, 3H) -quinazolinedione is used as it is or as a solution in an organic solvent such as dichloromethane, and this solution is adsorbed on a suitable carrier such as plastic such as polyethylene or rubber, or made of plastic. It is possible to obtain a practical form of a sex attractant using an appropriate material or device according to the capsule or the capillary mode.
[0012]
DETAILED DESCRIPTION OF THE INVENTION
[0013]
Below, the isolation and identification from the female adult of the component substance of the sex attractant concerning this invention and confirmation of the sex attractant activity about a chemical synthetic product are described in detail.
[0014]
(1) Identification of component substances [0015]
The tracking of component substances is a method of detecting changes in nerve potential generated when the antenna receives an active substance, using a bioassay that examines the attractiveness to adult males and a biodetector directly connected to a gas chromatograph. I did.
[0016]
The active component was examined using a gas chromatography / direct-contact antenna potential detector (GC-EAD) method using a non-polar column and directly extracting the female adults of Pleurotus communis with ether. As shown in FIG. 1, an EAD active peak was observed at 18.5 min. In the (GC-EAD) method using a polar column, an EAD active peak was observed at 19 min as shown in FIG.
[0017]
The extract was fractionated by column chromatography using silica gel (Wakogel C-200). That is, hexane, hexane ether (95: 5, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90), ether I flowed in the order. And most males were attracted to the hexane ether (40:60) fraction.
[0018]
Moreover, after concentrating the ether extract for 300 females of Uschakogane, it was injected into a gas chromatograph direct mass spectrometer (GC-MS analysis) and analyzed using an HP-5MS column, as shown in FIG. The molecular ion peak was found to be 190.
[0019]
Further, when this extract was analyzed by infrared gas chromatography, it was found that two amide groups were present as shown in FIG.
[0020]
From these analysis results, the chemical structure of the attractant was estimated to be 1,3-dimethyl (1H, 3H) -quinazolinedione as shown in FIG.
[0021]
When separately synthesized 1,3-dimethyl (1H, 3H) -quinazolinedione was compared by gas chromatography using a nonpolar column and a polar column, the retention time was consistent with the active natural product.
[0022]
From the above results, it was determined that the substance (natural product) having a very high attracting action against male adults of the genus Coleoptera belonging to the order Coleoptera is 1,3-dimethyl (1H, 3H) -quinazolinedione. .
[0023]
(2) Confirmation test of sex attraction activity of chemically synthesized substances [0024]
When 1,3-dimethyl (1H, 3H) -quinazolinedione obtained by chemical synthesis was subjected to gas chromatography / direct contact antenna potential detector (GC-EAD), the response of EAD was clearly recorded.
[0025]
【Example】
[0026]
Examples of the sex attractant according to the present invention will be described below.
[0027]
The sex attractant 1 according to the present invention was prepared by dissolving 1,3-dimethyl (1H, 3H) -quinazolinedione in an appropriate amount of dichloromethane as the sex pheromone attractant.
[0028]
And it was set as the
[0029]
Further, the sex attractant (1 mg) was impregnated into a pellet made of an ethylene vinyl acetate copolymer to obtain the sex attractant 12.
[0030]
[Test example]
[0031]
As the present invention zone 1, ten plastic containers containing the
[0032]
As the present invention zone 2, ten plastic containers containing the attractant 12 obtained in the above example were prepared.
[0033]
As a control, 10 empty plastic containers with nothing inside were prepared.
[0034]
Ten plastic containers of each section prepared above were set in plastic insect traps made by Japan Tobacco Inc., and 10 traps were prepared for each section.
[0035]
Using these traps, we conducted a trapping test on the mussel in the Asagiri Country Club in Shizuoka Prefecture from June 3 to June 4 under the same environmental conditions. I asked for a number.
[0036]
The test results were as shown in FIG.
[0037]
That is, the average number of insects per trap in the invention group 1 was 37 animals / 1 hour. In addition, the average number of insects per trap in the present invention group 2 was 153 / hour. In addition, the average number of insects per trap in the control group was 1.2 animals / 1 hour.
[0038]
As shown in the above results, it has been clarified that the present invention section shows a strong attractive force against Uschakogane.
[0039]
Considering the results of the above test examples, it was confirmed that the attractant according to the present invention has a very high attracting effect against male adults of the genus Coleoptera belonging to the order Coleoptera.
[0040]
【The invention's effect】
[0041]
According to the sex attractant of this invention, it has a high attracting effect with respect to the male male insect of Uschakogane, and is excellent in the control effect.
[Brief description of the drawings]
FIG. 1 is a graph showing the results of analysis of an extract of female adults of Uschakogane by the GC-EAD method using a non-polar column. FIG. 2 shows an extract of female adults of Uschakogane using a polar column. Graph showing the result of analysis by EAD method [Fig. 3] Graph showing the result of analysis by GC-MS analysis of the extract of females of Uschakogane [Fig. FIG. 5 is a graph showing the chemical structural formula of 1,3-dimethyl (1H, 3H) -quinazolinedione. FIG. 6 is a graph showing the insect trapping test results.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19161696A JP3814657B2 (en) | 1996-07-03 | 1996-07-03 | Uschakogane sex attractant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19161696A JP3814657B2 (en) | 1996-07-03 | 1996-07-03 | Uschakogane sex attractant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH1017418A JPH1017418A (en) | 1998-01-20 |
| JP3814657B2 true JP3814657B2 (en) | 2006-08-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19161696A Expired - Fee Related JP3814657B2 (en) | 1996-07-03 | 1996-07-03 | Uschakogane sex attractant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3814657B2 (en) |
-
1996
- 1996-07-03 JP JP19161696A patent/JP3814657B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH1017418A (en) | 1998-01-20 |
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