JP2003081718A - Ascotis selenaria cretacea communication-disturbing agent and communication-disturbing method using the same - Google Patents
Ascotis selenaria cretacea communication-disturbing agent and communication-disturbing method using the sameInfo
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、シャクガ科害虫で
あるヨモギエダシャクの性フェロモン交信を撹乱して交
尾率を下げ増殖を抑制し防除するヨモギエダシャクの交
信撹乱剤及びこれを用いた交信撹乱方法に関する。TECHNICAL FIELD [0001] The present invention relates to a mating disruption agent for Yomogieda shaku, which disturbs the sex pheromone communication of the pests of the genus Motifidae by disturbing the sex pheromone communication, thereby suppressing and controlling the mating rate, and a mating disruption method using the same. Regarding
【０００２】[0002]
【従来の技術】交信撹乱による害虫防除は、交信撹乱剤
である合成性フェロモンを害虫の発生場所の空気中に大
量に放出し、雌雄間の交信を撹乱させて交尾率を下げ、
次世代の幼虫密度を抑制するものである。交信撹乱剤に
使用されている合成性フェロモンは、毒性が極めて低く
環境汚染の心配がほとんど無い等、クリーンな害虫防除
手段として注目されている。Pest control by mating disruption releases a large amount of a mating disruptant, a synthetic pheromone, into the air at the site of the pest, disturbing mating between males and females, and lowering the mating rate.
It suppresses the larval density of the next generation. Synthetic pheromones used as communication disrupting agents are attracting attention as a clean pest control means because they have extremely low toxicity and little concern about environmental pollution.
【０００３】現在、交信撹乱剤は蛾類のハマキガ科、ス
ガ科、ヤガ科、ホソガ科、ハモグリガ科、ドクガ科等で
実用化されているが、蛾類最大の種数を有するシャクガ
科では交信撹乱に関する研究は手付かずであり、当然の
結果として実用化もなされていない。At present, communication disrupting agents have been put to practical use in the moths of the family Mothidae, Sugadidae, Mothidae, Hosogidae, Haridogariidae, and Gnatidae. Research on disturbance is untouched and, as a matter of course, has not been put to practical use.
【０００４】シャクガ科害虫の交信撹乱剤が開発されて
こなかった原因として、シャクガ科の性フェロモン成分
がエポキシド化合物であることが挙げられる。ハマキガ
類をはじめとするこれまで同定されてきた多くの蛾類性
フェロモン成分は、直鎖不飽和の酢酸エステルやアルコ
ールやアルデヒドである。これら性フェロモンの化学合
成は研究が進み、比較的高純度の化合物でも安価な合成
が可能となっている。しかし、シャクガ科の性フェロモ
ンであるエポキシド化合物は、光学活性を有するため高
純度の合成品を低コストで大量に得ることが難しく、合
成サンプルを大量に必要とする交信撹乱の技術には馴染
まないと考えられてきた。[0004] The reason why the mating disruptive agent for the pests of the Geometridae family has not been developed is that the sex pheromone component of the Geometridae family is an epoxide compound. Many of the moth sex pheromone components that have been identified so far, such as the leaf tortoises, are linear unsaturated acetic acid esters, alcohols and aldehydes. The chemical synthesis of these sex pheromones has been studied, and it is possible to inexpensively synthesize a compound having a relatively high purity. However, since the epoxide compound, a sex pheromone of the Geometridae family, has optical activity, it is difficult to obtain a high-purity synthetic product in large quantities at low cost, and it is unsuitable for communication disruption technology that requires a large amount of synthetic samples. Has been considered.
【０００５】[0005]
【発明が解決しようとする課題】しかし、シャクガ科害
虫には広食性の害虫が多く、その防除に大量の殺虫剤が
使用されている現状から、シャクガ科害虫に対する交信
撹乱剤の開発が要望されている。そこで、本発明者ら
は、シャクガ科害虫であり、チャや果樹の重要害虫であ
るヨモギエダシャクに注目し、本害虫を防除するために
有効な交信撹乱剤を提供しようとするものである。However, because of the widespread insect pests of the Geometridae family and the large amount of insecticides used for their control, the development of a communication disruption agent against the Pestidae family is demanded. ing. Therefore, the present inventors pay attention to Momogydashak, which is an important pest of the Convolvulaceae family and an important pest of tea and fruit trees, and intends to provide an effective interfering agent for controlling this pest.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、かかる課
題を解決するために、ヨモギエダシャクの性フェロモン
に関して鋭意研究を重ねた結果、シス−３，４−エポキ
シ−（６Ｚ，９Ｚ）−ノナデカジエン（cis-3,4-epoxy-
(6Z,9Z)-nonadecadiene）(以下、「化合物Ａ」と略
す。)と、シス−６，７−エポキシ−（３Ｚ，９Ｚ）−
ノナデカジエン（cis-6,7-epoxy-(3Z,9Z)-nonadecadien
e）（以下、「化合物Ｂ」と略す。）と、シス−９，１
０−エポキシ−（３Ｚ，６Ｚ）−ノナデカジエン（cis-
9,10-epoxy-(3Z,6Z)-nonadecadiene）（以下、「化合物
Ｃ」と略す。）とを含み、好ましくは（３Ｚ，６Ｚ，９
Ｚ）−ノナデカトリエン（(3Z,6Z,9Z)-nonadecatrien
e）（化合物Ｄと略す。）を含むことにより、本種の防
除に非常に有効であることを知見し、本発明をなすに至
ったものである。各化合物の構造式を以下に示す。Means for Solving the Problems In order to solve the above problems, the inventors of the present invention have conducted earnest studies on the sex pheromone of the mugwort, resulting in cis-3,4-epoxy- (6Z, 9Z)- Nonadecadien (cis-3,4-epoxy-
(6Z, 9Z) -nonadecadiene) (hereinafter abbreviated as "Compound A") and cis-6,7-epoxy- (3Z, 9Z)-
Nonadecadien (cis-6,7-epoxy- (3Z, 9Z) -nonadecadien
e) (hereinafter abbreviated as “compound B”) and cis-9,1
0-epoxy- (3Z, 6Z) -nonadecadiene (cis-
9,10-epoxy- (3Z, 6Z) -nonadecadiene) (hereinafter abbreviated as “compound C”), and preferably (3Z, 6Z, 9
Z) -Nonadecatrien ((3Z, 6Z, 9Z) -nonadecatrien
It was found that the inclusion of e) (abbreviated as compound D) is very effective in controlling this species, and the present invention has been completed. The structural formula of each compound is shown below.
【０００７】[0007]
【化１】 [Chemical 1]
【０００８】[0008]
【発明の実施の形態】以下、本発明につき更に詳しく説
明する。ヨモギエダシャクの性フェロモンは、化合物Ａ
と同定された（Ａｎｄｏ ｅｔ．ａｌ．Ｊｏｕｒｎａｌ
ｏｆ Ｃｈｅｍｉｃａｌ Ｅｃｏｌｏｇｙ １９９
７，２３，２４１３〜２４２３）。また、同時に、本種
の処女雌の性フェロモン腺には化合物Ｄが検出され、性
フェロモンの前駆体としてのみならず性フェロモンとし
ても作用している可能性が示唆された。The present invention will be described in more detail below. The sex pheromone of the mugwort Daedak is compound A
(Ando et. Al. Journal
of Chemical Ecology 199
7, 23, 2413-2423). At the same time, Compound D was detected in the sex pheromone gland of the virgin female of this species, suggesting that it may act as a sex pheromone as well as a precursor of the sex pheromone.
【０００９】化合物Ａの合成には、化合物Ｄを経由し、
これをメタクロロ過安息香酸（ＭＣＰＢＡ）にて酸化す
る経路が一般的である（Ａｎｄｏ ｅｔ．ａｌ．Ｊｏｕ
ｒｎａｌ ｏｆ Ｃｈｅｍｉｃａｌ Ｅｃｏｌｏｇｙ
１９９３，１９，７８７〜７９８）。この酸化反応で
は、化合物Ａは選択的に生成せず、化合物Ａと化合物Ｂ
と化合物Ｃが同時に生成する。これら各位置異性体は蒸
留等の簡便な精製法ではほとんど分離しないため、ロー
バーカラムを備えた中圧液体クロマトグラフィー（ＭＰ
ＬＣ）での分離等、高コストな方法が必要となる。さら
に、光学異性体を分離するには、キラルカラムを用いた
高圧液体クロマトグラフィーが必要となり、以上の手法
で作られた合成品は、農業用目的で使用することは困難
なほど高価なものとなる。To synthesize compound A, via compound D,
A common pathway is to oxidize this with metachloroperbenzoic acid (MCPBA) (Ando et. Al. Jou.
rnal of Chemical Ecology
1993, 19, 787-798). In this oxidation reaction, the compound A is not selectively produced, and the compound A and the compound B are not generated.
And compound C are simultaneously produced. Since these positional isomers are hardly separated by a simple purification method such as distillation, medium pressure liquid chromatography (MP) equipped with a row bar column is used.
A costly method such as separation by LC) is required. Furthermore, high-pressure liquid chromatography using a chiral column is required to separate the optical isomers, and the synthetic products produced by the above methods are expensive and difficult to use for agricultural purposes. .
【００１０】本発明者らは、ヨモギエダシャクの交信撹
乱に関して検討した結果、化合物Ｄの酸化反応により得
られる化合物Ａと化合物Ｂと化合物Ｃとの混合物を交信
撹乱剤として用いることにより、ヨモギエダシャクの性
フェロモンそのものを交信撹乱剤とするよりも防除効果
が高いことを見いだし、さらに、上記混合物に対して化
合物Ｄが１〜１０．０重量％添加されている場合さらに
防除効果が高いことを見い出し本発明の完成に至った。The inventors of the present invention have studied the communication disruption of Artemisia alba, and as a result, by using a mixture of Compound A, Compound B and Compound C obtained by the oxidation reaction of Compound D as a communication disruptor, It was found that the control effect is higher than when the sex pheromone itself is used as a communication disrupting agent, and further, the control effect is higher when 1 to 10.0% by weight of compound D is added to the above mixture. The invention was completed.
【００１１】本発明の交信撹乱剤として用いられる３種
のエポキシド化合物の混合比率は、化合物Ｄを経由して
得られる合成過程ではほぼ１：１：１の割合（重量比）
で生成するが、その割合は厳密ではなく任意で構わな
い。実際に交信撹乱剤として使用する場合、化合物Ａと
化合物Ｂと化合物Ｃとの総重量に対する化合物Ａの重量
が、１０〜９０重量％、特に２０〜６０重量％が好まし
い。これらエポキシド化合物は、ラセミ体で十分効果を
発揮するが、光学純度の高い合成品でも良い。また、化
合物Ｄからの酸化反応条件により、ジエポキシド化合物
やトリエポキシド化合物が生成されるが、これらの不純
物は、好ましくは１０重量％以内であれば、交信撹乱効
果に大きな影響を及ぼさない。The mixing ratio of the three epoxide compounds used as the communication disrupting agent of the present invention is approximately 1: 1: 1 (weight ratio) in the synthetic process obtained via compound D.
However, the ratio is not strict and may be arbitrary. When actually used as a communication disrupting agent, the weight of compound A relative to the total weight of compound A, compound B and compound C is preferably 10 to 90% by weight, particularly preferably 20 to 60% by weight. Although these epoxide compounds exert a sufficient effect in a racemic form, they may be synthetic products having high optical purity. Further, a diepoxide compound or a triepoxide compound is produced depending on the oxidation reaction condition from the compound D, but these impurities do not have a great influence on the communication disrupting effect as long as they are preferably within 10% by weight.
【００１２】さらに、本発明における交信撹乱剤は、ヨ
モギエダシャク以外の昆虫であっても、（Ｚ）−体の二
重結合を３−位、６−位、９−位に有する炭素数１９の
直鎖不飽和のモノエポキシド化合物を性フェロモンとし
て利用している昆虫であれば、高い交信撹乱活性を有す
ることが容易に推測される。このような昆虫は、表１に
示すように、シャクガ科で２１種、ヤガ科で３種すでに
報告されている。Further, the mating disruption agent of the present invention has 19 carbon atoms having a double bond of (Z) -form at 3-position, 6-position and 9-position, even in insects other than Artemisia alba. It is easily inferred that insects utilizing a linear unsaturated monoepoxide compound as a sex pheromone have a high mating disruption activity. As shown in Table 1, such insects have already been reported in 21 species in the Geometridae and 3 species in the family Mothidae.
【００１３】[0013]
【表１】 [Table 1]
【００１４】本発明の交信撹乱剤は、有効成分として含
有する上記合成性フェロモン物質を長期間にわたって徐
々に放出させるために、ポリエチレン、ポリプロピレ
ン、エチレン−酢酸ビニール共重合体等の放出量制御機
能を有するプラスチックからなる細管、ラミネート製の
袋、アンプル等の容器に充填して用いられる。さらに、
製剤化にあたっては、ブチルヒドロキシトルエン（ＢＨ
Ｔ）、ビタミンＥ等の抗酸化剤や紫外線吸収剤を適当量
加えてもよい。本発明の交信撹乱剤の好ましい使用量
は、害虫の発生量や気象又は地形等の諸条件により異な
るが、通常１０〜２００ｇ／ｈａである。The mating disruptant of the present invention has a function of controlling the amount of release of polyethylene, polypropylene, ethylene-vinyl acetate copolymer, etc. in order to gradually release the synthetic pheromone substance contained as an active ingredient over a long period of time. It is used by filling it in a thin tube made of plastic, a laminated bag, a container such as an ampoule. further,
Butyl hydroxytoluene (BH
T), vitamin E and other antioxidants and UV absorbers may be added in appropriate amounts. The preferred amount of the mating disruptive agent of the present invention to be used is usually 10 to 200 g / ha, although it varies depending on various conditions such as the amount of pests generated, weather and topography.
【００１５】以下、本発明の具体的態様を実施例及び比
較例によって説明するが、本発明はこの記述に限定され
るものではないSpecific embodiments of the present invention will be described below with reference to Examples and Comparative Examples, but the present invention is not limited to these descriptions.
【実施例】実施例１〜２及び比較例１〜３
実施例１〜２及び比較例１〜３の各例において、表２に
示すように、化合物Ａと化合物Ｂと化合物Ｃの混合物
(重量比１：１：１)又は化合物Ａを調製し、これに安定
剤としてＢＨＴと２−（２′−ヒドロキシ−３′−ｔｅ
ｒｔ−ブチル−５′−メチルフェニル）−５−クロロヘ
ンゾトリアゾール（住友化学社製スミソーブ３００）を
各３重量％添加し、外径１．４１ｍｍ、内径０．８１ｍ
ｍ、長さ２０ｃｍのポリエチレンチューブに封じ込め、
徐放性の交信撹乱剤とした。各チューブには、約８０ｍ
ｇを充填した。それぞれの化合物は、ラセミ体を使用
し、不純物としてジエポシ化合物とトリエポキシド化合
物は、合計１０重量％未満である。Examples Examples 1 and 2 and Comparative Examples 1 to 3 In each of Examples 1 to 2 and Comparative Examples 1 to 3, as shown in Table 2, a mixture of compound A, compound B and compound C
(Weight ratio 1: 1: 1) or compound A was prepared and added with BHT and 2- (2'-hydroxy-3'-te as stabilizers.
3 wt% each of rt-butyl-5'-methylphenyl) -5-chlorohenzotriazole (Sumisorb 300 manufactured by Sumitomo Chemical Co., Ltd.) was added, and the outer diameter was 1.41 mm and the inner diameter was 0.81 m.
m, polyethylene tube with a length of 20 cm
It was used as a sustained release communication disrupting agent. About 80m for each tube
g. Each compound uses a racemate, and the total amount of the diepoxy compound and the triepoxide compound as impurities is less than 10% by weight.
【００１６】[0016]
【表２】 [Table 2]
【００１７】これら交信撹乱剤を、各０．１ｈａのチャ
園に表２の交信撹乱剤を１０ａあたり１００本及び３０
０本処理し、性フェロモントラップを用いた交信撹乱率
調査と幼虫調査により防除効果判を行った。その結果を
表３に示した。なお、比較例３は、交信撹乱剤処理を行
わなかった慣行防除による対照区である。Each of the communication disrupting agents was added to a tea garden of 0.1 ha, and 100 and 30 of the communication disrupting agents shown in Table 2 per 10a were used.
The control effect was judged by the treatment of 0 plants and the investigation of the mating disturbance rate using the sex pheromone trap and the larvae survey. The results are shown in Table 3. Comparative Example 3 is a control group by the conventional control in which the treatment of the communication disrupting agent was not performed.
【００１８】交信撹乱率は、交信撹乱剤を処理した圃場
と無処理圃場に、それぞれ設置したフェロモントラップ
の誘殺数から、以下の式により求めた。The mating disruption rate was calculated by the following formula from the number of pheromone traps installed in the field treated with the mating disruptant and in the untreated field.
【式１】 [Formula 1]
【００１９】また、幼虫調査は、各圃場において任意に
５０カ所を選び、そのポイントを中心として５０ｃｍ×
５０ｃｍの範囲のチャ葉に寄生している幼虫数を数える
ことにより行い、１ｍ3当たりの幼虫数として表記し
た。In the larva survey, 50 points were arbitrarily selected in each field, and the point was the center of 50 cm ×
It was performed by counting the number of larvae parasitizing tea leaves in the range of 50 cm, and expressed as the number of larvae per 1 m 3 .
【００２０】[0020]
【表３】 [Table 3]
【００２１】実施例１や実施例２では、高い交信撹乱率
を示し、また、１ｍ3あたりの幼虫数も０．８頭と０．
２頭と非常に少なかった。しかし、比較例１や比較例２
では、交信撹乱剤を無処理の比較例３に比べ、幼虫数が
少なかったものの、４．５頭と２．８頭の幼虫が認めら
れた。交信撹乱率も最大で９０．３％とそれほど高くな
かった。In Examples 1 and 2, a high rate of mating disruption was exhibited, and the number of larvae per m 3 was 0.8, which was 0.8.
It was very small with only two. However, Comparative Example 1 and Comparative Example 2
In comparison, the number of larvae was smaller than that of Comparative Example 3 which was not treated with the mating disruption agent, but 4.5 and 2.8 larvae were observed. The communication disruption rate was 90.3% at maximum, which was not so high.
【００２２】実施例３〜６
化合物Ａと化合物Ｂと化合物Ｃの混合物(重量比１：
１：１)に対して、化合物Ｄを１％（実施例３）、５％
（実施例４）、１０％（実施例５）、２０％（実施例
６）を添加したものを前述のポリエチレンチューブにそ
れぞれ封入し、各０．１ｈａのチャ園に、１０ａあたり
１００本の割合で処理した。そして、交信撹乱率と幼虫
数を前述の方法により調べた。それらの結果を表４に示
す。なお、表４には、対照として実施例１の結果と、交
信撹乱剤処理を行わなかった慣行防除による対照区に関
する比較例３の結果も示す。Examples 3 to 6 A mixture of compound A, compound B and compound C (weight ratio 1:
1%) to 1% of Compound D (Example 3), 5%
(Example 4) 10% (Example 5) and 20% (Example 6) were added to the polyethylene tubes described above, and the ratio was 100 per 10a in each 0.1 ha tea garden. Processed in. Then, the contact disruption rate and the number of larvae were examined by the method described above. The results are shown in Table 4. In addition, Table 4 also shows the result of Example 1 as a control and the result of Comparative Example 3 regarding the control group by the conventional control without the treatment of the communication disrupting agent.
【００２３】[0023]
【表４】 [Table 4]
【００２４】実施例１では、９９．１％の交信撹乱率と
幼虫数も０．８頭と、比較的高い防除効果を示している
ものの、実施例３〜５ではさらに高い交信撹乱率と防除
効果を示していることがわかる。また、化合物Ｄを２０
重量％添加した実施例６では、交信撹乱率、防除効果と
もに実施例３〜５に比べるとやや劣るが、比較例に比べ
ると防除効果を示していることがわかる。In Example 1, the mating disruption rate was 99.1% and the number of larvae was 0.8, showing a relatively high control effect, but in Examples 3 to 5, a higher mating disruption rate and control. It can be seen that the effect is shown. In addition, compound D is 20
It is understood that in Example 6 in which the content by weight was added, both the communication disturbing rate and the control effect were slightly inferior to those in Examples 3 to 5, but the control effect was exhibited as compared with the comparative examples.
【００２５】[0025]
【発明の効果】本発明による交信撹乱剤によれば、ヨモ
ギエダシャクに対して極めて強力に作用するので、その
防除に有効である。INDUSTRIAL APPLICABILITY The communication disrupting agent according to the present invention exerts an extremely strong action against Artemisia terrestris, and is therefore effective in controlling it.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 望月 文昭 新潟県中頸城郡頸城村大字西福島28番地の １ 信越化学工業株式会社合成技術研究所 内 (72)発明者 福本 毅彦 新潟県中頸城郡頸城村大字西福島28番地の １ 信越化学工業株式会社合成技術研究所 内 Ｆターム(参考） 2B121 AA12 CC14 EA26 FA16 4H011 AC07 BA01 BB01 BB08 DB04 ─────────────────────────────────────────────────── ─── Continued front page (72) Inventor Fumiaki Mochizuki 28, Nishi-Fukushima 1 Shin-Etsu Chemical Co., Ltd. Synthesis Technology Laboratory Within (72) Inventor Takehiko Fukumoto 28, Nishi-Fukushima 1 Shin-Etsu Chemical Co., Ltd. Synthesis Technology Laboratory Within F term (reference) 2B121 AA12 CC14 EA26 FA16 4H011 AC07 BA01 BB01 BB08 DB04
Claims (3)
Ｚ）−ノナデカジエンと、シス−６，７−エポキシ−
（３Ｚ，９Ｚ）−ノナデカジエンと、シス−９，１０−
エポキシ−（３Ｚ，６Ｚ）−ノナデカジエンとを含むこ
とを特徴とするヨモギエダシャクの交信撹乱剤。1. A cis-3,4-epoxy- (6Z, 9
Z) -Nonadecadiene and cis-6,7-epoxy-
(3Z, 9Z) -Nonadecadiene and cis-9,10-
An agent for disturbing communication of the mugwort Daedak, which comprises epoxy- (3Z, 6Z) -nonadecadiene.
トリエンを含むことを特徴とするヨモギエダシャクの交
信撹乱剤。2. A mating disruption agent for wormwood dasak, which further comprises (3Z, 6Z, 9Z) -nonadecatriene.
を用いたヨモギエダシャクの交信撹乱方法。3. A method for disrupting communication of Momogyida shrimp using the communication disrupting agent according to claim 1 or 2.
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|---|---|---|---|
| JP2001279144A JP3853184B2 (en) | 2001-09-14 | 2001-09-14 | Artemisia dasaku communication disruptor and communication disruption method using the same |
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| JP3853184B2 JP3853184B2 (en) | 2006-12-06 |
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