JP6108548B2 - Pest resistance inducer and plant pest control method - Google Patents
Pest resistance inducer and plant pest control method Download PDFInfo
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- JP6108548B2 JP6108548B2 JP2013166598A JP2013166598A JP6108548B2 JP 6108548 B2 JP6108548 B2 JP 6108548B2 JP 2013166598 A JP2013166598 A JP 2013166598A JP 2013166598 A JP2013166598 A JP 2013166598A JP 6108548 B2 JP6108548 B2 JP 6108548B2
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- loriolide
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- resistance inducer
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Description
本発明は、植物の病虫害抵抗性を増強させる化合物を有効成分として含有する害虫抵抗性誘導剤、及び当該化合物を利用した植物の害虫防除方法に関する。 The present invention relates to a pest resistance inducer containing as an active ingredient a compound that enhances plant pest resistance, and a plant pest control method using the compound.
作物の収量低下を招く病害虫の発生は、農業分野において深刻な問題である。指定有害動植物による被害の半数以上が害虫による被害であり、害虫防除は重要である。作物にかかる害虫の防除方法には様々な技術があるが、主に、殺虫剤等の化学農薬を使用する化学的防除法や、抵抗性品種や天敵を利用する方法等の生物学的防除法が用いられている。中でも、化学農薬は即効性があり、防除効果も高いため、多用されている。しかしながら、化学農薬には、不適切な使用による環境中への残留による生態系への影響や、同一薬剤の連続使用により薬剤抵抗性を持った害虫の出現の問題が懸念されている。また、環境保全や消費者の安全志向の観点からも、化学農薬の使用量の低減が求められている。これらのニーズに呼応して減農薬農業が実施されているが、通常使用量では顕在化しなかった病害虫の発生も問題となっている。 The occurrence of pests that reduce crop yields is a serious problem in the agricultural field. More than half of the damage caused by designated pests is caused by pests, and pest control is important. There are various techniques for controlling pests on crops, but mainly biological control methods using chemical pesticides such as insecticides and methods using resistant varieties and natural enemies. Is used. Among them, chemical pesticides are frequently used because they have an immediate effect and a high control effect. However, for chemical pesticides, there are concerns about the impact on the ecosystem due to improper use in the environment and the emergence of pests with drug resistance due to continuous use of the same drug. In addition, from the viewpoints of environmental protection and consumer safety, the use of chemical pesticides is required to be reduced. In response to these needs, agricultural pesticide reduction is being implemented, but the occurrence of pests that did not become apparent with normal use amounts is also a problem.
生物学的防除法の場合には、化学農薬によるこれらの問題は生じないが、別の問題がある。例えば、通常の品種にかえて抵抗性品種を栽培した場合には、抵抗性を打破する害虫の出現が問題となっている。このため、近年では抵抗性が崩壊することなく安定的に持続する特性を有する品種が求められている。また、天敵を利用する方法では、十分な効果を示す天敵の常時調達が困難である。 In the case of biological control methods, these problems with chemical pesticides do not arise, but there are other problems. For example, when resistant cultivars are cultivated instead of ordinary varieties, the appearance of pests that break resistance is a problem. For this reason, in recent years, there is a demand for varieties having the characteristic of stably sustaining resistance without collapsing. In addition, in the method using natural enemies, it is difficult to constantly procure natural enemies that exhibit sufficient effects.
近年、環境保全型病害防除手法として病害抵抗性誘導物質が注目されている。病害抵抗性誘導物質は、化学農薬と異なり、病原体を直接殺すものではなく、植物が本来有する病害抵抗性を誘導・強化することで病害を防除するものである。広範囲な病原体に効果があり、その効果も長期間持続する特徴がある。植物の病害抵抗性の機構は種を超えて保存されていることから抵抗性誘導物質がその生理活性を示す植物種の範囲は広い。 In recent years, disease resistance inducers have attracted attention as environmental conservation type disease control methods. Unlike chemical pesticides, disease resistance inducers do not directly kill pathogens but control diseases by inducing and strengthening the disease resistance inherent in plants. It is effective against a wide range of pathogens, and the effect is also long-lasting. Since the mechanism of plant disease resistance is preserved across species, there is a wide range of plant species in which the resistance inducer exhibits its physiological activity.
ナス科植物であるトマトやアブラナ科植物であるシロイヌナズナなどを用いた研究により植物の病害抵抗性経路は、生きた植物細胞から栄養を得るウイルスなどの活物寄生性病原体に対して有効なサリチル酸経路と、宿主細胞を殺して栄養にする灰色カビ病菌などの殺生性病原体に対して有効なジャスモン酸・エチレン系との２つに大別できることが示されている（例えば、非特許文献１参照。）。いもち病菌は、両者の中間的な振る舞いを示す半活物寄生性病原体であるが、その抵抗性にはサリチル酸経路が関与する。例えば、現在までに、イネいもち病など一部の病気に対して有効な抵抗性誘導物質が実用化に成功している。 The disease resistance pathway of plants has been determined by research using solanaceous plants such as tomatoes and cruciferous plants such as Arabidopsis plants. The salicylic acid pathway is effective against parasitic parasites such as viruses that obtain nutrients from living plant cells. And jasmonic acid / ethylene system which is effective against biocidal pathogens such as gray mold fungus that kills and nurtures host cells (see, for example, Non-Patent Document 1). ). Blast fungus is a semi-active parasitic pathogen that exhibits an intermediate behavior between the two, but the salicylic acid pathway is involved in its resistance. For example, a resistance inducer effective for some diseases such as rice blast has been successfully put to practical use.
一方で、ロリオライドは、植物や藻類等の光合成を行う多くの生物種に存在しているモノテルペンラクトンである。植物等からメタノールやクロロホルム等の有機溶剤により抽出されたロリオライドは、抗酸化作用（例えば、非特許文献２参照。）や免疫抑制作用（例えば、特許文献１参照。）を有することが知られている。ロリオライドは、その他、β−カロテンの酸化等の各種合成反応によっても合成することができる（非特許文献３及び４、特許文献２参照。）。 On the other hand, Loriolide is a monoterpene lactone that exists in many biological species that perform photosynthesis, such as plants and algae. Loriolide extracted from plants or the like with an organic solvent such as methanol or chloroform is known to have an antioxidant action (for example, see Non-Patent Document 2) and an immunosuppressive action (for example, see Patent Document 1). Yes. Loriolide can also be synthesized by various synthetic reactions such as oxidation of β-carotene (see Non-Patent Documents 3 and 4 and Patent Document 2).
現在見つかっている抵抗性誘導物質のほとんどが活物寄生性病原体に効果を示すタイプであり、殺生性病原体や害虫に効果のある物質は全くといってよいほど知られていない。 Most of the resistance-inducing substances currently found are effective against active parasite pathogens, and no substances that are effective against biocidal pathogens or pests are known.
なお、植物ホルモンのジャスモン酸は、植物の害虫抵抗性のシグナル伝達経路を活性化することから害虫に対する抵抗性誘導物質とみなすことができ、殺生性病原体や害虫への効果が期待できる。しかしながら、ジャスモン酸は、その施用によって生長抑制や分化異常などの農業上好ましくない形質を起こす可能性があることに加えて、製造コストが高いことから、現時点では実用レベルの防除剤候補にはなりえない。 In addition, since the plant hormone jasmonic acid activates a pest-resistant signal transduction pathway of plants, it can be regarded as a resistance inducer against pests, and can be expected to have an effect on biocidal pathogens and pests. However, jasmonic acid is a candidate for a practical control agent at present because of its high production costs in addition to its potential to cause undesirable growth traits such as growth inhibition and abnormal differentiation due to its application. No.
そこで、本発明は、害虫に対して有効であり、害虫防除剤として有用な新たな抵抗性誘導剤、及び当該抵抗性誘導剤を用いた植物の害虫防除方法を提供することを目的とする。 Therefore, an object of the present invention is to provide a new resistance inducer that is effective against pests and is useful as a pest control agent, and a plant pest control method using the resistance inducer.
本発明者らは、害虫に対する抵抗性を誘導する物質を見出すべく、天然資源に焦点を絞り、病虫害抵抗性が誘発された植物を用いて探索を試みた結果、カロテノイドの一種であるロリオライド及びその異性体であるエピロリオライドが、直接的に殺虫活性を有さないにも関わらず、ナミハダニやハスモンヨトウといった害虫に対する優れた抵抗性能を植物に誘導することを見出し、本発明を完成させた。 In order to find a substance that induces resistance against pests, the present inventors focused on natural resources and attempted to search using plants in which disease resistance was induced, and as a result, loriolide, a kind of carotenoid and its It has been found that the isomer, Epyrroliolide, induces a plant with excellent resistance against insect pests such as the spider mite and Spodoptera spp., Although it does not have direct insecticidal activity, and has completed the present invention.
すなわち、本発明は、ロリオライド、エピロリオライド、又はこれらの混合物を有効成分として含有することを特徴とする、害虫抵抗性誘導剤を提供する。
前記害虫抵抗性誘導剤としては、チョウ目昆虫又はハダニ類に対する抵抗性を誘導するものが好ましい。
本発明は、また、前記害虫抵抗性誘導剤を、植物体に接触又は吸収させることを特徴とする、植物の害虫防除方法を提供する。
前記植物の害虫防除方法においては、防除対象の害虫としては、チョウ目昆虫又はハダニ類が好ましく、防除される植物としては、ナス科植物又はアブラナ科植物が好ましい。
That is, the present invention provides an insect pest resistance inducer characterized by containing loriolide, epipyrrolide, or a mixture thereof as an active ingredient.
The insect pest resistance inducer is preferably one that induces resistance to Lepidoptera insects or spider mites.
The present invention also provides a method for controlling plant pests, characterized in that the insect pest resistance inducer is brought into contact with or absorbed by a plant body.
In the plant pest control method, the pests to be controlled are preferably lepidopterous insects or spider mites, and the plant to be controlled is preferably a solanaceous plant or cruciferous plant.
本発明に係る害虫抵抗性誘導剤は、植物体の害虫に対する抵抗性を誘起させて害虫防除効果を示す。このため、当該害虫抵抗性誘導剤及びこれを用いた植物の害虫防除方法は、抵抗性系統の出現のおそれが非常に小さく、環境保護の点からも好ましい害虫防除方法である。 The pest resistance inducer according to the present invention induces the resistance of plant bodies to pests and exhibits a pest control effect. Therefore, the pest resistance inducer and the plant pest control method using the pest resistance inducer have a very low risk of appearance of resistant lines, and are preferable pest control methods from the viewpoint of environmental protection.
本発明に係る害虫抵抗性誘導剤は、ロリオライド、エピロリオライド、又はこれらの混合物を有効成分として含有することを特徴とする。ロリオライド及びその異性体であるエピロリオライドは、下記式（１）及び（２）でそれぞれ表される化合物である。ロリオライド及びエピロリオライドは、殺虫活性は示さないが、植物の害虫防除活性を高めることができる。 The insect pest resistance inducer according to the present invention is characterized by containing loriolide, epipyrrolide, or a mixture thereof as an active ingredient. Loriolide and its isomer, epriliolide, are compounds represented by the following formulas (1) and (2), respectively. Loriolide and epipyrrolide do not exhibit insecticidal activity, but can enhance the insect pest control activity of plants.
本発明において用いられるロリオライド及びエピロリオライドは、天然物からの抽出物であってもよい。ロリオライド及びエピロリオライドは、カロテノイドの代謝産物であり、カロテノイド代謝経路を有する植物や藻類に多く含まれる。これらの植物や藻類からの抽出物には、多くの場合、ロリオライドとエピロリオライドは２：１の割合で含有されている。 An extract from a natural product may be used as the loriolide and the epyrrolide used in the present invention. Loriolide and epipyrrolide are metabolites of carotenoids and are abundant in plants and algae having carotenoid metabolic pathways. In many cases, the extracts from these plants and algae contain loriolide and epipyrrolide in a ratio of 2: 1.
ロリオライド及びエピロリオライドは、カロテノイド代謝経路を有する植物や藻類のうち、特にガマズミ（Viburnum dilatatum）、センダン（Melia azedarach）、トチュウ（Eucommia ulmoides）、ローズマリー（Rosmarinus officinalis）、サルビア（Salvia splendens）、タイワンノイバラ（Rosa taiwanensis）、ドクムギ（Lolium temulentum）、ツユクサ（Commelina communis）、ジギタリス (Digitalis sp.)、ケール（Brassica oleracea var． acephala）ヤナギモク（Sargassum ringgoldianum ssp. coreanum）、ヒジキ（Sargassum fusiforme）、エツキイワノカワ（Peyssonnelia caulifera）等に多く含まれている。これらの植物や藻類からロリオライド及びエピロリオライドを抽出することができる。また、タバコモザイクウイルスの感染に伴って起こるタバコ（Nicotiana tabacum）の過敏感反応の過程でロリオライド及びエピロリオライドの内生量は増加するため、過敏感反応が起きたタバコ葉からも、多くのロリオライドとエピロリオライドを得ることができる。 Loriolides and epipyrrolides are among the plants and algae that have carotenoid metabolic pathways, especially Viburnum dilatatum, Melia azedarach, Eucommia ulmoides, Rosemaryus officinalis, Salvia splendens, and Thai ones. (Rosa taiwanensis), Japanese wheat (Lolium temulentum), Japanese cypress (Commelina communis), Digitalis sp. caulifera) etc. Loriolide and epipyrrolide can be extracted from these plants and algae. In addition, the endogenous amount of loriolide and pyrroliolide increases in the process of the hypersensitive reaction of tobacco (Nicotiana tabacum) caused by the infection with tobacco mosaic virus. Epipyrrolide can be obtained.
植物等からのロリオライド等の抽出は、有機溶剤を用いて常法により行うことができる（例えば、特許文献１、非特許文献２等参照）。具体的には、例えば、ロリオライド等を含む植物の葉や茎等の生鮮物や乾燥物から、メタノール、エタノール、クロロホルム等の有機溶媒を用いて抽出する。植物等の乾燥物は、天日乾燥や自然乾燥等の乾燥処理を行ったものであってもよく、液体窒素による急速凍結を行ったものであってもよい。また、有機溶媒を添加する前に、予め細断又は粉砕しておくことも好ましい。得られた抽出物は、減圧蒸留等により濃縮した後、分液ロートを用いて有機溶媒層を分取することにより、ロリオライド等を含む粗抽出物を得ることができる。この粗抽出物は、そのまま、又は必要に応じて濃縮した後、本発明に係る害虫抵抗性誘導剤の有効成分として使用できる。
Extraction of loriolide and the like from plants and the like can be performed by a conventional method using an organic solvent (see, for example,
本発明に係る害虫抵抗性誘導剤の有効成分としては、前記粗抽出物を、クロマトグラフィー法により精製した精製抽出物を用いることも好ましい。例えば、前記粗抽出物を、順相のシリカゲルクロマトグラフィーにかけてロリオライド等を含む画分を分離してもよい。前記粗抽出物をシリカゲルカラムにアプライし、ヘキサンと酢酸エチルの混合溶媒で溶出した場合には、ロリオライド等は、酢酸エチルの濃度が容量比で７５〜８５％を占めるヘキサンと酢酸エチルの混合溶媒で溶出される画分に溶出される。そこで、この画分を、そのまま、又は必要に応じて濃縮した後、本発明に係る害虫抵抗性誘導剤の有効成分として使用できる。また、シリカゲルカラマトグラフィーにより得られたロリオライド等を含む画分を、さらに逆相クロマトグラフィーにかけることにより、ロリオライド及びエピロリオライドをより高純度に精製することができる。 As an active ingredient of the pest resistance inducer according to the present invention, it is also preferable to use a purified extract obtained by purifying the crude extract by a chromatography method. For example, the crude extract may be subjected to normal phase silica gel chromatography to separate a fraction containing loroliide or the like. When the crude extract is applied to a silica gel column and eluted with a mixed solvent of hexane and ethyl acetate, Loriolide etc. is a mixed solvent of hexane and ethyl acetate in which the concentration of ethyl acetate occupies 75 to 85% by volume. Eluted in the fraction eluted at Therefore, this fraction can be used as an active ingredient of the pest resistance inducer according to the present invention as it is or after being concentrated as necessary. Further, by subjecting a fraction containing loroliide and the like obtained by silica gel calamography to reverse phase chromatography, loriolide and epipyrrolide can be purified with higher purity.
本発明において用いられるロリオライド及びエピロリオライドは、合成品であってもよい。ロリオライド等は、公知の合成方法により合成することができる。例えば、ロリオライド又はエピロリオライドは、クロロホルムに溶解させたルテイン（キサントフィル）とメチレンブルーに対して光酸化反応させることによって合成することができる（非特許文献３参照。）。また、例えば、４−（２−ブテニリデン）−３，５，５−トリメチル−２−シクロヘキセン−１−オンから、オゾン分解し、得られた分解物を還元して２，６，６−トリメチル−４−オキソ−１−シクロヘキセニルアセトアルデヒドを得、これを酸化し、得られた，６，６−トリメチル−４−オキソ−１−シクロヘキセニル酢酸を還元後にラクトン化することにより、ロリオライド及びエピロリオライドが得られる（特許文献２参照。）。 Synthetic products may be used for the loriolide and the epyrrolide used in the present invention. Loriolide and the like can be synthesized by a known synthesis method. For example, loriolide or epipyrrolide can be synthesized by photooxidizing a lutein (xanthophyll) dissolved in chloroform and methylene blue (see Non-Patent Document 3). Further, for example, ozonolysis from 4- (2-butenylidene) -3,5,5-trimethyl-2-cyclohexen-1-one, and the resulting decomposition product is reduced to produce 2,6,6-trimethyl- 4-Oxo-1-cyclohexenylacetaldehyde was obtained, oxidized, and the resulting 6,6-trimethyl-4-oxo-1-cyclohexenylacetic acid was reduced and then lactonized to obtain lorolide and epyrrolide. (See Patent Document 2).
本発明に係る害虫抵抗性誘導剤の有効成分とするロリオライド等は、溶媒和物であってもよく、塩として含有されていてもよい。溶媒和物としては、例えば、水、メタノール 、エタノール、酢酸エチル等の溶媒和物が挙げられる。また、塩としては、例えば、ナトリウム塩、カリウム塩、リチウム塩等のアルカリ金属塩；カルシウム塩、マグネシウム塩等のアルカリ土類金属塩；アルミニウム塩、鉄塩、亜鉛塩、銅塩、ニッケル塩等の金属塩；酢酸塩、アンモニウム塩等の無機塩；ジベンジルアミン塩、グルコサミン塩、エチレンジアミン塩、ジエチルアミン塩、トリエチルアミン塩、ジシクロヘキシルアミン塩、ジエタノールアミン塩、テトラメチルアンモニア塩等の有機アミン塩；グリシン塩、リジン塩、アルギニン塩、オルニチン塩、アスパラギン塩等のアミノ酸塩等が挙げられる。 The loliolide used as the active ingredient of the pest resistance inducer according to the present invention may be a solvate or may be contained as a salt. Examples of the solvate include solvates such as water, methanol, ethanol, and ethyl acetate. Examples of the salt include alkali metal salts such as sodium salt, potassium salt and lithium salt; alkaline earth metal salts such as calcium salt and magnesium salt; aluminum salt, iron salt, zinc salt, copper salt and nickel salt Inorganic salts such as acetate and ammonium salts; Organic amine salts such as dibenzylamine salt, glucosamine salt, ethylenediamine salt, diethylamine salt, triethylamine salt, dicyclohexylamine salt, diethanolamine salt and tetramethylammonium salt; glycine salt Amino acid salts such as lysine salt, arginine salt, ornithine salt and asparagine salt.
本発明に係る害虫抵抗性誘導剤におけるロリオライド及びエピロリオライドの濃度は、植物体の害虫防除活性を誘起するために充分な濃度であればよく、防除対象である害虫の種類、害虫抵抗性誘導剤が使用（散布）される対象植物の種類、一度の散布時における散布量、散布頻度等を考慮して適宜決定される。なお、ロリオライドとエピロリオライドの害虫防除活性誘起作用はほぼ同等である。このため、本発明に係る害虫抵抗性誘導剤としては、ロリオライドとエピロリオライドを任意の割合で混合したものであってもよい。例えば、害虫防除効果と一度の散布量との兼ね合いから、植物体への施用（散布）時における本発明に係る害虫抵抗性誘導剤中のロリオライドとエピロリオライドの合計濃度は、１０μＭ（ｍｏｌ／Ｌ）以上が好ましく、１００μＭ以上がより好ましく、３００μＭ以上がさらに好ましい。ロリオライド及びエピロリオライドの合計濃度が、１０μＭ未満のときには、害虫防除効果が十分に得られないおそれがある。一方で、ロリオライド及びエピロリオライドは光合成を行う生物種のほとんど全てにおいて生産される物質であり、多くの食品に含まれていることから、環境や人体に与える影響は小さいと推察される。このため、本発明に係る害虫抵抗性誘導剤中のロリオライド及びエピロリオライドの合計濃度の上限値は、特に規定されないが、費用の点等から２０００μＭ以下が好ましく、１０００μＭ以下がより好ましく、７００μＭ以下がさらに好ましく、５００μＭ以下がよりさらに好ましい。 The concentration of loriolide and epipyrrolide in the pest resistance inducer according to the present invention may be a concentration sufficient to induce the pest control activity of the plant body, and the type of pest to be controlled, the pest resistance inducer is It is appropriately determined in consideration of the type of target plant to be used (dispersed), the amount of application at the time of one application, the application frequency, etc. In addition, the pest control activity-inducing action of loriolide and epipyrrolide is almost the same. Therefore, the pest resistance inducer according to the present invention may be a mixture of loriolide and epipyrrolide in an arbitrary ratio. For example, from the balance between the pest control effect and the amount of spraying once, the total concentration of loriolide and epipyrrolide in the pest resistance inducer according to the present invention at the time of application (spraying) to a plant body is 10 μM (mol / L). The above is preferable, 100 μM or more is more preferable, and 300 μM or more is further preferable. When the total concentration of loriolide and epipyrrolide is less than 10 μM, the pest control effect may not be sufficiently obtained. On the other hand, loriolide and epriliolide are substances produced in almost all biological species that carry out photosynthesis, and since they are contained in many foods, it is presumed that they have little impact on the environment and the human body. For this reason, the upper limit of the total concentration of loriolide and epipyrrolide in the pest resistance inducer according to the present invention is not particularly specified, but is preferably 2000 μM or less, more preferably 1000 μM or less, and more preferably 700 μM or less from the viewpoint of cost. Preferably, 500 μM or less is even more preferable.
なお、本発明に係る害虫抵抗性誘導剤は、植物体への施用時に希釈して使用する濃縮物であってもよい。例えば、本発明に係る害虫抵抗性誘導剤のロリオライドとエピロリオライドの合計濃度を１ｍＭ〜１Ｍとした場合には、使用時に水やエタノール等の適当な溶媒で１００倍〜１０００００倍希釈して有効成分濃度を所望の濃度（例えば、１０μＭ程度）に調整して使用することができる。 In addition, the pest resistance inducer according to the present invention may be a concentrate used by diluting when applied to a plant body. For example, when the total concentration of the pest resistance inducer Loriolide and Epyrroliolide according to the present invention is 1 mM to 1 M, the active ingredient concentration is diluted 100 to 100000 times with an appropriate solvent such as water or ethanol at the time of use. Can be used after adjusting to a desired concentration (for example, about 10 μM).
本発明に係る害虫抵抗性誘導剤の剤型としては、特に限定されるものではなく、例えば、粉剤、粒剤、錠剤、水和剤、乳剤、水溶剤、油剤、エアロゾル剤等が挙げられる。本発明に係る害虫抵抗性誘導剤を農業園芸用として用いる場合には、植物体への散布等が容易であることから、水和剤、乳剤、水溶剤、油剤、エアロゾル剤、粉剤等が好ましく、植物体への吸収性の点から、水和剤、乳剤、水溶剤、エアロゾル剤がより好ましい。これらの製剤は、常法に従って製造することができる。例えば、有効成分（ロリオライド及び／又はエピロリオライド）を、不活性な液体（溶媒）又は固体の担体で希釈し、必要に応じてその他の添加剤をこれに加えて、各種製剤を製造する。当該添加剤としては、例えば、界面活性剤、賦形剤、結合剤、崩壊剤、滑沢剤、着色料、矯臭剤、ｐＨ調整剤等が挙げられる。 The dosage form of the pest resistance inducer according to the present invention is not particularly limited, and examples thereof include powders, granules, tablets, wettable powders, emulsions, aqueous solvents, oils, and aerosols. When the pest resistance inducer according to the present invention is used for agricultural or horticultural purposes, it is preferable to use a wettable powder, emulsion, aqueous solvent, oil, aerosol, powder, etc., because it can be easily applied to plants. From the viewpoint of absorbability to plants, a wettable powder, emulsion, aqueous solvent, and aerosol are more preferred. These preparations can be produced according to a conventional method. For example, an active ingredient (Loriolide and / or Epyrolide) is diluted with an inert liquid (solvent) or a solid carrier, and other additives are added thereto as necessary to produce various preparations. Examples of the additive include a surfactant, an excipient, a binder, a disintegrant, a lubricant, a colorant, a flavoring agent, and a pH adjuster.
本発明に係る害虫抵抗性誘導剤が水溶剤や水和剤等の液状の剤型である場合、ロリオライド及び／又はエピロリオライドを溶解又は分散させる溶媒としては、ロリオライド等に対して不活性であり、かつ対象となる植物体に悪影響を及ぼしにくい溶媒が好ましい。当該溶媒としては、メタノール、エタノール、及び水などが適宜使用される。水溶剤の場合、例えば、ロリオライド、エピロリオライド、又はこれらの混合物を、メタノールやエタノールに溶解させ、得られた溶液を水で希釈することにより調製できる。 When the insect pest resistance inducer according to the present invention is a liquid dosage form such as an aqueous solvent or a wettable powder, the solvent for dissolving or dispersing loroliide and / or epyriolide is inactive against loroliide, etc. And the solvent which does not have a bad influence on the plant body used as object is preferable. As the solvent, methanol, ethanol, water and the like are appropriately used. In the case of an aqueous solvent, for example, it can be prepared by dissolving lorolide, epipyrrolide, or a mixture thereof in methanol or ethanol and diluting the resulting solution with water.
本発明に係る害虫抵抗性誘導剤は、ロリオライド及びエピロリオライドによる害虫防除活性誘起効果を阻害しない範囲内で、その他の殺虫剤や殺菌剤、除草剤、植物生長調節剤、肥料等を含有していてもよい。 The insect pest resistance inducer according to the present invention contains other insecticides, fungicides, herbicides, plant growth regulators, fertilizers, etc., as long as they do not inhibit the insect pest control activity-inducing effect of loriolide and epipyrrolide. Also good.
ロリオライド及びエピロリオライドは、植物体の害虫防除活性、特に、食葉性害虫及び吸汁性害虫に対する防除活性を誘起し、これらの害虫に対する抵抗性を増強させることができる。このため、本発明に係る害虫抵抗性誘導剤により処理された植物体では、食葉性害虫による食害やハダニ類による吸汁害が低減する。また、この害虫抵抗性誘導効果から、ロリオライド及びエピロリオライドは、チョウ目昆虫やハダニ類等の害虫に対する抵抗性誘導剤のリード化合物としての利用も期待できる。 Loriolide and epipyrrolide can induce plant pest control activity, particularly control activity against phytophagous and sucking pests, and can enhance resistance to these pests. For this reason, in the plant processed with the insect pest resistance inducer according to the present invention, the damage caused by the leafy insects and the sucking damage caused by the mites are reduced. In addition, from this insect pest resistance inducing effect, loliolide and epyrroliolide can be expected to be used as lead compounds for resistance inducers against insect pests such as lepidopterous insects and spider mites.
本発明に係る害虫抵抗性誘導剤により防除対象となる害虫のうち、食葉性害虫としては、チョウ目の昆虫が好ましく、ハスモンヨトウ（Spodoptera litura）、シロイチモジヨトウ（Spodoptera exigua）、ヨトウガ（Mamestra brassicae）、シロシタヨトウ（Sarcopolia illoba）、コナガ（Plutella xylostella）、タマナギンウワバ（Autographa nigrisigna）、ハイマダラノメイガ（Hellula undalis）、タバコガ（Helicoverpa assulta）、オオタバコガ（Helicoverpa armigera）、又はモンシロチョウ（Pieris rapae）等がより好ましく、ハスモンヨトウ、シロイチモジヨトウがさらに好ましい。また、本発明に係る害虫抵抗性誘導剤により防除対象となる害虫のうち、吸汁性害虫としては、ハダニが好ましく、カンザワハダニ（Tetranychus kanzawai）又はナミハダニ（Tetranychus urticae）が好ましい。 Among the pests to be controlled by the pest resistance inducer according to the present invention, the leafy pest is preferably an insect of the order Lepidoptera, Spodoptera litura, Spodoptera exigua, Mamestra brassicae, Pterella larva (Sarcopolia illoba), Plutella xylostella, Autographa nigrisigna, Hellula undalis, Tobacco moth (Helicoverpa assulta), Tobacco moth (Helicoverpa armigera), P. More preferred is Shirochimodojito. Of the pests to be controlled by the pest resistance inducer according to the present invention, the sucking pest is preferably a spider mite (Tetranychus kanzawai) or a spider mite (Tetranychus urticae).
本発明に係る植物の害虫防除方法は、本発明に係る害虫抵抗性誘導剤を、植物体に接触又は吸収させることを特徴とする。本発明に係る害虫抵抗性誘導剤を植物体に接触又は吸収させることにより、有効成分たるロリオライド等が植物体に作用し、当該植物体の病害抵抗性が増強され、食葉性害虫による食害やハダニ類による吸汁害を低減させることができる。 The plant pest control method according to the present invention is characterized in that the pest resistance inducer according to the present invention is brought into contact with or absorbed into a plant body. By contacting or absorbing the insect pest resistance inducer according to the present invention to the plant body, the active ingredient Loriolide or the like acts on the plant body, the disease resistance of the plant body is enhanced, Juice damage caused by spider mites can be reduced.
本発明に係る害虫抵抗性誘導剤は、防除活性誘起効果が充分に発揮されるため、植物体に吸収させることが好ましいが、植物体の表面に接触させるだけであってもよい。当該表面からもロリオライド等は植物体に作用し得るためである。 The pest resistance inducer according to the present invention is preferably absorbed in the plant body because the control activity inducing effect is sufficiently exhibited, but it may be merely brought into contact with the surface of the plant body. This is because Loriolide and the like can also act on the plant body from the surface.
本発明に係る植物の害虫防除方法において、本発明に係る害虫抵抗性誘導剤を、植物体に接触又は吸収させる方法は、特に限定されるものではなく、その他の農薬等を散布する方法と同様にして行うことができる。本発明に係る害虫抵抗性誘導剤が液状の剤型である場合には、そのまま、又は適宜水やエタノール等の適当な溶媒で希釈した後に、植物体の葉や茎等の表面に塗布する方法や、噴霧する方法が好ましい。塗布処理や噴霧処理は、通常の葉面散布と同様の方法で行うことができる。その他、液状の害虫抵抗性誘導剤又はその希釈液を、植物体が植えられている土壌にまいてもよい。害虫抵抗性誘導剤を土壌にまいた場合には、有効成分であるロリオライド等が根から植物体へ吸収される。また、本発明に係る害虫抵抗性誘導剤が粉剤の場合には、そのまま、又は適宜水やエタノール等の適当な溶媒に分散させた分散液を、塗布処理や噴霧処理することができる。本発明に係る害虫抵抗性誘導剤が粒剤等の比較的大きな固形の場合には、植物体が植えられている土壌にまくことができる。 In the plant pest control method according to the present invention, the method for bringing the pest resistance inducer according to the present invention into contact with or absorbing the plant body is not particularly limited, and is the same as the method for spraying other agricultural chemicals and the like. Can be done. When the insect pest resistance inducer according to the present invention is in a liquid dosage form, the method is applied as it is or after appropriately diluting with an appropriate solvent such as water or ethanol, and then applied to the surface of a plant leaf, stem, etc. Or the method of spraying is preferable. The coating process and the spraying process can be performed by the same method as that for normal foliar spraying. In addition, a liquid pest resistance inducer or a diluted solution thereof may be dispersed in the soil in which the plant body is planted. When a pest resistance inducer is spread in soil, loriolide, which is an active ingredient, is absorbed from the roots to the plant body. In addition, when the pest resistance inducer according to the present invention is a powder, a dispersion liquid dispersed as appropriate or in an appropriate solvent such as water or ethanol can be applied or sprayed. When the pest resistance inducer according to the present invention is a relatively large solid such as a granule, it can be planted in the soil in which the plant is planted.
本発明に係る植物の害虫防除方法において、対象植物体に対する本発明に係る害虫抵抗性誘導剤の施用量は、対象植物体の種類、防除対象である害虫の種類、被害の程度、環境条件、害虫抵抗性誘導剤の有効成分含有量や剤型等を考慮して適宜決定される。本発明においては、充分な害虫防除効果が得られやすいため、植物体への施用時におけるロリオライドとエピロリオライドの合計濃度が、１０μＭ以上、好ましくは１００μＭ以上、より好ましくは３００μＭ以上となるように本発明に係る害虫抵抗性誘導剤を施用することが好ましい。 In the plant pest control method according to the present invention, the application amount of the pest resistance inducer according to the present invention to the target plant is the type of the target plant, the type of pest to be controlled, the degree of damage, the environmental conditions, It is determined appropriately in consideration of the active ingredient content and dosage form of the pest resistance inducer. In the present invention, since a sufficient pest control effect is easily obtained, the total concentration of loriolide and epipyrrolide at the time of application to a plant body is 10 μM or more, preferably 100 μM or more, more preferably 300 μM or more. It is preferable to apply a pest resistance inducer according to the above.
本発明に係る植物の害虫防除方法において、対象となる植物体としては、食害性害虫又は吸汁性害虫による害が生じ得る植物であれば特に限定されるものではないが、市場で取引される植物であることが好ましく、野菜類、花き類、果樹、チャ等の農作物や観葉植物がより好ましい。なかでも野菜類が好ましく、トマト、ナス、ピーマン、パプリカ、ジャガイモ、トウガラシ等のナス科の植物、及び、キャベツ、ブロッコリー、メキャベツ、カイワレダイコン、カブ、ダイコン、カリフラワー、コマツナ、タアサイ、チンゲンサイ、ナバナ、ハクサイ、ミズナ、ラディッシュ等のアブラナ科の植物がさらに好ましく、トマトがよりさらに好ましい。 In the plant pest control method according to the present invention, the target plant body is not particularly limited as long as it is a plant that can cause damage by pests or sucking pests, but plants that are traded in the market Agricultural crops such as vegetables, flowers, fruit trees, tea, and houseplants are more preferable. Of these, vegetables are preferred, and solanaceous plants such as tomatoes, eggplants, peppers, paprika, potatoes, and peppers, and cabbage, broccoli, pea cabbage, silkworm radish, turnip, radish, cauliflower, komatsuna, taasai, chingensai, nabana, Chinese cabbage More preferred are cruciferous plants such as Mizuna and radish, and even more preferred are tomatoes.
以下、実施例等により本発明を更に詳細に説明するが、本発明は、その要旨を変更しない限り以下の実施例等に限定されるものではない。 EXAMPLES Hereinafter, although an Example etc. demonstrate this invention further in detail, this invention is not limited to a following example etc., unless the summary is changed.
［実施例１］
＜植物粗抽出画分２４時間処理のナミハダニ産卵数に対する防除効果の検定＞
ロリオライド及びエピロリオライドを、タバコモザイクウイルスを感染させたタバコモザイクウイルス抵抗性タバコ品種ＳａｍｓｕｎＮＮから抽出し、得られた粗精製物の植物の害虫抵抗性誘起効果を調べた。
[Example 1]
<Test of control effect on the number of spider mite spawned by 24 hours of crude plant extract fraction>
Loriolide and epipyrrolide were extracted from tobacco mosaic virus-resistant tobacco cultivar SamsunNN infected with tobacco mosaic virus, and the effect of inducing the insect pest resistance of the resulting crude product was examined.
まず、タバコ品種ＳａｍｓｕｎＮＮの葉に対して、予め１０ｍＭリン酸緩衝液（ｐＨ７．０）で１Ｌあたり１０ｍｇのタバコモザイクウイルスを含むように調製したウイルス液を、カーボランダム（炭化ケイ素）とともに葉表面を擦ることによって接種した。擦った時点から３０分後に、葉の表面の余分なウイルス液を水で洗い流した後、接種した植物体全体を３０℃の恒温室内で４８時間栽培し、次いで２０℃の恒温室に移して引き続き４８時間栽培した。 First, a virus solution prepared so as to contain 10 mg of tobacco mosaic virus per liter in 10 mM phosphate buffer (pH 7.0) on the leaves of tobacco cultivar SamsunNN was applied to the leaf surface together with carborundum (silicon carbide). Inoculated by rubbing. 30 minutes after the rubbing, the excess virus solution on the leaf surface was washed away with water, and then the whole inoculated plant was cultivated in a constant temperature room at 30 ° C. for 48 hours, and then transferred to a constant temperature room at 20 ° C. Cultivated for 48 hours.
（抽出）
栽培後のウイルスを接種させた葉を、液体窒素で急速に凍結し、乳鉢と乳棒を用いて抹茶状になるまで細かく砕いた。得られた破砕物に、葉新鮮重に対して重量（質量）比で４倍量のメタノールを加え、さらに乳棒ですり潰した。得られた摩砕液をビーカーに移し、４℃の冷蔵庫で２４時間静置させた。摩砕液を濾紙で濾過した後、濾液をロータリーエバポレーターを用いて減圧下３０℃で水層を得るまで濃縮した。得られた水層に、容量比で等量の酢酸エチルを混合し、分液ロートを用いて溶媒抽出を行った。分取した上層（酢酸エチル層）は、無水硫酸ナトリウムで脱水した後、ロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮した。
(Extraction)
The leaves inoculated with the virus after cultivation were rapidly frozen with liquid nitrogen and crushed into green tea using a mortar and pestle. Four times the amount of methanol was added to the crushed material in a weight (mass) ratio with respect to the fresh weight of the leaf, and further ground with a pestle. The obtained grinding liquid was transferred to a beaker and allowed to stand in a refrigerator at 4 ° C. for 24 hours. After the milled liquid was filtered with filter paper, the filtrate was concentrated using a rotary evaporator at 30 ° C. under reduced pressure until an aqueous layer was obtained. The resulting aqueous layer was mixed with an equal amount of ethyl acetate in a volume ratio, and solvent extraction was performed using a separatory funnel. The separated upper layer (ethyl acetate layer) was dehydrated with anhydrous sodium sulfate, and then concentrated to dryness at 30 ° C. under reduced pressure using a rotary evaporator.
（粗精製）
得られた濃縮物を１ｍＬのヘキサン酢酸エチル（６：１）混合溶媒（ヘキサンと酢酸エチルの容量比が６：１となる混合液）に溶解させ、得られた濃縮溶液を、その最上部に予め水とメタノールで洗浄した海砂を積層させた上でヘキサン酢酸エチル（６：１）混合溶媒で平衡化させておいた分取用シリカゲル６０（和光純薬社製）を充填したガラスクロマト管に添加し、カラム容量の３倍量のヘキサン酢酸エチル（６：１）混合溶媒を通液し、次いでヘキサン中の酢酸エチル濃度を段階的に上昇させた混合溶媒を順次通液し、最後にアセトンを通液することで溶出した。以降、ヘキサンと酢酸エチル濃度が容量比で６：１の混合溶媒で溶出された画分を［６／１］画分、ヘキサンと酢酸エチル濃度が容量比で３：１の混合溶媒で溶出された画分を［３／１］画分、ヘキサンと酢酸エチル濃度が容量比で１：１の混合溶媒で溶出された画分を［１／１］画分、ヘキサンと酢酸エチル濃度が容量比で１：３の混合溶媒で溶出された画分を［１／３］画分、ヘキサンと酢酸エチル濃度が容量比で１：６の混合溶媒で溶出された画分を［１／６］画分、アセトンで溶出された画分をアセトン溶出画分という。ロリオライド及びエピロリオライドは、［１／３］画分と［１／６］画分（酢酸エチル濃度が７５％〜８５％のヘキサン酢酸エチル混合溶媒溶出画分）に含まれていた。各溶出画分を、ロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮し、得られた濃縮物をメタノールに溶解させ、水によって最終濃度が１００ｐｐｍになるように希釈した。
(Rough purification)
The obtained concentrate was dissolved in 1 mL of a mixed solvent of hexane ethyl acetate (6: 1) (a mixture of hexane and ethyl acetate in a volume ratio of 6: 1), and the resulting concentrated solution was placed on the top. A glass chromatograph tube packed with preparative silica gel 60 (manufactured by Wako Pure Chemical Industries, Ltd.) that had been previously laminated with sea sand washed with water and methanol and equilibrated with a mixed solvent of hexane ethyl acetate (6: 1). Then, 3 times the column volume of the hexane ethyl acetate (6: 1) mixed solvent was passed through, then the mixed solvent with the ethyl acetate concentration in hexane increased stepwise, and finally Elution was performed by passing acetone. Thereafter, the fraction eluted with a mixed solvent having a hexane / ethyl acetate concentration of 6: 1 by volume is eluted with a [6/1] fraction, and the fraction eluted with a mixed solvent having a hexane / ethyl acetate concentration of 3: 1 by volume. The fraction eluted with [3/1] fraction, and the fraction eluted with 1: 1 mixed solvent of hexane and ethyl acetate in the volume ratio [1/1] fraction, hexane and ethyl acetate concentration in the volume ratio Fraction eluted with 1: 3 mixed solvent in [1/3] fraction, and fraction eluted with 1: 6 hexane and ethyl acetate concentration by volume in [1/6] fraction The fraction eluted with acetone is called the acetone-eluted fraction. Loriolide and epipyrrolide were contained in the [1/3] and [1/6] fractions (the fraction eluted with a mixed solvent of hexane-ethyl acetate having an ethyl acetate concentration of 75% to 85%). Each eluted fraction was concentrated using a rotary evaporator at 30 ° C. under reduced pressure until it was completely dried, and the resulting concentrate was dissolved in methanol and diluted with water to a final concentration of 100 ppm.
次いで、３〜４週齢のトマト葉の第３、４、５位葉を、各溶出画分溶液に浸漬させ、２５℃±１℃の恒温室内に置いた。２４時間後、トマト葉を蒸留水で洗い、風乾した後、ガラス板（７．５ｃｍ×２．５ｃｍ）上に置いた予め水を含ませた脱脂綿の上に載せ、さらにその上にアクリル製マンジャーセル（７．５ｃｍ×２．５ｃｍ、 セル内径：１．５ｃｍ）を載せた。セル内に３日齢の予め交尾した３０頭のナミハダニ雌成虫を置き、カバーガラスでセルを覆った後、２５℃±１℃、１５時間明期／９時間暗期条件下で制御した恒温室内に置いた。５日後に、トマト葉に産下された卵の数を計測した。各溶出画分溶液に代えて、０．１容量％のメタノール水溶液で２４時間同様に処理したものを、対照区とした。 Subsequently, the 3rd, 4th, and 5th leaves of tomato leaves 3 to 4 weeks old were immersed in each elution fraction solution and placed in a thermostatic chamber at 25 ° C. ± 1 ° C. After 24 hours, the tomato leaves were washed with distilled water, air-dried, and then placed on a pre-watered absorbent cotton placed on a glass plate (7.5 cm × 2.5 cm). A jar cell (7.5 cm × 2.5 cm, cell inner diameter: 1.5 cm) was placed. In a cell-controlled room controlled under 25 ° C ± 1 ° C, 15 hours light period / 9 hours dark period conditions after placing 30-day pre-mating adult female urticae in a cell and covering the cell with a cover glass Put it on. After 5 days, the number of eggs laid on the tomato leaves was counted. Instead of each elution fraction solution, a solution treated in the same manner with a 0.1% by volume methanol aqueous solution for 24 hours was used as a control group.
図１に、トマトにおけるナミハダニ産卵数に対するタバコモザイクウイルス感染タバコ葉から調製した各溶出画分溶液の２４時間処理の効果を示す。ロリオライド及びエピロリオライドを含有する［１／３］画分と［１／６］画分で処理したトマト葉では、０．１容量％メタノールのみを処理した対照区と比較して、ナミハダニ産卵数の低下が認められた。 FIG. 1 shows the effect of 24-hour treatment of each elution fraction solution prepared from tobacco mosaic virus-infected tobacco leaves on the number of spider mite eggs in tomato. In the tomato leaves treated with the [1/3] and [1/6] fractions containing loriolide and epipyrrolide, the number of spider mite spawning decreased compared to the control group treated with only 0.1% methanol by volume Was recognized.
本実施例において示すように、ロリオライド及びエピロリオライドは、粗抽出物でも、精製したロリオライド等と同様に害虫防除効果を有する。つまり、ロリオライドやエピロリオライドなどのカロテノイドを多量に生産する植物の粗抽出物等は、直接的又は間接的に防除資材等として利用し得る。精製前の粗抽出物を利用できれば、より安価に有効成分を調製し得るため、経済的なインパクトも大きいと期待される。 As shown in the present Example, loriolide and epipyrrolide have a pest control effect even in a crude extract, as in the case of refined loriolide. That is, a plant crude extract or the like that produces a large amount of carotenoids such as loriolide or epipyrrolide can be used directly or indirectly as a control material or the like. If the crude extract before purification can be used, an active ingredient can be prepared at a lower cost.
［製造例１］
実施例１において得られた［１／３］画分と［１／６］画分（ロリオライド及びエピロリオライドを含有する粗抽出画分）から、ロリオライド及びエピロリオライドを精製した。
[Production Example 1]
From the [1/3] fraction and the [1/6] fraction obtained in Example 1 (crude extract fraction containing loriolide and epipyrrolide), loriolide and epipyrrolide were purified.
（精製）
まず、［１／３］画分と［１／６］画分を混合し、ロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮した。得られた乾固物を少量のメタノールで溶解させ、ＨＰＬＣ（高速液体クロマトグラフィー）用逆相カラム（Ａｔｌａｎｔｉｓ Ｐｒｅｐ Ｔ３ ＯＢＤ、１９ｍｍ（内径）×１５０ｍｍ（長さ）、Ｗａｔｅｒｓ社製）に注入した。水／メタノールを、当該カラムの溶出に用いる移動相とし、１分あたり１０ｍＬの流速にて１５分間にわたりメタノール濃度を３０容量％から１００容量％にリニアに上昇させるグラジエント溶出を行った。保持時間５．２〜６．５分の間に溶出された画分を分取し、ロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮した。得られた乾固物を、少量のアセトニトリルで溶解させ、ＨＰＬＣ用逆相カラム（Ｌｉｃｈｒｏｓｐｈｅｒ ＲＰ−１８、４．６ｍｍ（内径）×１５０ｍｍ（長さ）、Ａｇｉｌｅｎｔ社製）に注入した。水／アセトニトリルをカラムの溶出に用いる移動相とし、１分あたり０．８ｍＬの流速にて６０分間にわたりアセトニトリル濃度を２０％から１００％にリニアに上昇させるグラジエント溶出を行った。保持時間４９．０〜５２．０分の間に溶出された物質がロリオライド及びエピロリオライドであった。この結果、過敏感反応が起きたタバコ葉新鮮重１．５ｋｇからのロリオライドとエピロリオライドの収量は、それぞれ７．５ｍｇと２．９ｍｇであった。
(Purification)
First, the [1/3] fraction and the [1/6] fraction were mixed and concentrated using a rotary evaporator until complete drying at 30 ° C. under reduced pressure. The dried product thus obtained was dissolved in a small amount of methanol and injected into a reversed phase column for HPLC (High Performance Liquid Chromatography) (Atlantis Prep T3 OBD, 19 mm (inner diameter) × 150 mm (length), manufactured by Waters). Water / methanol was used as a mobile phase for elution of the column, and gradient elution was performed to linearly increase the methanol concentration from 30% by volume to 100% by volume at a flow rate of 10 mL per minute for 15 minutes. Fractions eluted during a retention time of 5.2 to 6.5 minutes were collected and concentrated to complete dryness at 30 ° C. under reduced pressure using a rotary evaporator. The obtained dried product was dissolved in a small amount of acetonitrile, and injected into a reverse phase column for HPLC (Lichrosphere RP-18, 4.6 mm (inner diameter) × 150 mm (length), manufactured by Agilent). Gradient elution was performed in which water / acetonitrile was used as the mobile phase for column elution, and the acetonitrile concentration was linearly increased from 20% to 100% over 60 minutes at a flow rate of 0.8 mL per minute. The substances eluted during the retention time of 49.0-52.0 minutes were Loriolide and Epiloride. As a result, the yields of loriolide and epipyrrolide from 1.5 kg of fresh tobacco leaf weight that caused a hypersensitive reaction were 7.5 mg and 2.9 mg, respectively.
［製造例２］
過敏感反応が起きたタバコ葉に代えて、過敏感反応を起こしていないタバコ葉を用いて、実施例１と同様にしてロリオライド及びエピロリオライドを含有する粗抽出画分（［１／３］画分と［１／６］画分）を得、次いでこの粗抽出画分から製造例１と同様にしてロリオライドとエピロリオライドを精製した。この結果、過敏感反応前のタバコ葉新鮮重１ｋｇからのロリオライドとエピロリオライドの収量は、それぞれ２１μｇと８．５μｇであった。
[Production Example 2]
In place of the tobacco leaf in which the hypersensitive reaction occurred, the tobacco leaf that did not cause the hypersensitive reaction was used, and a crude extract fraction ([1/3] fraction containing loriolide and epyrroliolide was used in the same manner as in Example 1. And [1/6] fraction), and then, from this crude extract fraction, loriolide and epipyrrolide were purified in the same manner as in Production Example 1. As a result, the yields of loriolide and epipyrrolide from 1 kg of fresh tobacco leaf weight before the hypersensitive reaction were 21 μg and 8.5 μg, respectively.
［製造例３］
過敏感反応が起きたタバコ葉に代えて、ガマズミ、トチュウ、及びヒジキをそれぞれ用いて、実施例１と同様にしてロリオライド及びエピロリオライドを含有する粗抽出画分（［１／３］画分と［１／６］画分）を得、次いでこの粗抽出画分から製造例１と同様にしてロリオライドとエピロリオライドを精製した。この結果、乾燥重１ｋｇのガマズミ、トチュウ、ヒジキから、それぞれロリオライドとエピロリオライドの混合物を１３．３ｍｇ、６．０ｍｇ、６．２ｍｇ得ることができた。
[Production Example 3]
In place of the tobacco leaf in which the hypersensitive reaction occurred, viburnum, eucommia and hijiki were used, respectively, in the same manner as in Example 1, and then a crude extract fraction containing a loriolide and an epyrrolide ([1/3] fraction and [ 1/6] fraction), and then, from this crude extract fraction, loriolide and epipyrrolide were purified in the same manner as in Production Example 1. As a result, it was possible to obtain 13.3 mg, 6.0 mg, and 6.2 mg of a mixture of loriolide and epipyrrolide from 1 kg of viburnum, eucommia, and hijiki, respectively.
［製造例４］
ルテインから光酸化反応により、ロリオライドとエピロリオライドを合成した。
まず、ルテイン（ＵＳＢｉｏｌｏｇｉｃａｌ社製）５００ｍｇとメチレンブルー１０ｍｇを５００ｍＬのクロロホルムに溶解し、その溶液を１Ｌ容のナス型フラスコに入れ、３７Ｗの蛍光灯下で２４時間撹拌しながら光酸化反応を行った。反応終了後、反応液を酢酸エチルで抽出し、得られた酢酸エチル抽出物をロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮した。
得られた濃縮物を１ｍＬのヘキサン酢酸エチル（６：１）混合溶媒（ヘキサンと酢酸エチルの容量比が６：１となる混合液）に溶解させ、得られた濃縮溶液から、実施例１の粗精製工程と同様にしてロリオライド及びエピロリオライドを含有する粗抽出画分（［１／３］画分と［１／６］画分）を得た。
[Production Example 4]
Loriolide and epyrrolide were synthesized from lutein by photo-oxidation reaction.
First, 500 mg of lutein (manufactured by US Biological) and 10 mg of methylene blue were dissolved in 500 mL of chloroform, and the solution was placed in a 1 L eggplant-shaped flask and subjected to a photooxidation reaction with stirring under a 37 W fluorescent lamp for 24 hours. After completion of the reaction, the reaction solution was extracted with ethyl acetate, and the obtained ethyl acetate extract was concentrated to complete dryness at 30 ° C. under reduced pressure using a rotary evaporator.
The obtained concentrate was dissolved in 1 mL of a mixed solvent of hexane ethyl acetate (6: 1) (a mixture of hexane and ethyl acetate in a volume ratio of 6: 1). In the same manner as in the crude purification step, crude extract fractions ([1/3] fraction and [1/6] fraction) containing loriolide and epipyrrolide were obtained.
（精製）
次いで、［１／３］画分と［１／６］画分を混合し、ロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮した。得られた乾固物を少量のメタノールで溶解させ、ＨＰＬＣ（高速液体クロマトグラフィー）用逆相カラム（Ａｔｌａｎｔｉｓ Ｐｒｅｐ Ｔ３ ＯＢＤ、１９ｍｍ（内径）×１５０ｍｍ（長さ）、Ｗａｔｅｒｓ社製）に注入した。水／メタノールを、当該カラムの溶出に用いる移動相とし、１分あたり１０ｍＬの流速にて１５分間にわたりメタノール濃度を３０容量％から１００容量％にリニアに上昇させるグラジエント溶出を行った。保持時間５．２〜６．５分の間に溶出された画分を分取し、ロータリーエバポレーターを用いて減圧下３０℃で完全に乾固するまで濃縮した。得られた乾固物を、少量のアセトニトリルで溶解させ、ＨＰＬＣ用逆相カラム（Ｓｕｎｆｉｒｅ ｐｒｅｐ Ｃ１８、１０ｍｍ（内径）×１５０ｍｍ（長さ）、Ｗａｔｅｒｓ社製）に注入した。水とアセトニトリルが容積比で６０：４０の混合液をカラムの溶出に用いる移動相とし、１分あたり１ｍＬの流速にて通液し、ロリオライド及びエピロリオライドを含む画分を得た。この結果、生成物としてロリオライド２６ｍｇ、エピロリオライド２０ｍｇを得た。
(Purification)
Next, the [1/3] fraction and the [1/6] fraction were mixed and concentrated using a rotary evaporator until complete drying at 30 ° C. under reduced pressure. The dried product thus obtained was dissolved in a small amount of methanol and injected into a reversed phase column for HPLC (High Performance Liquid Chromatography) (Atlantis Prep T3 OBD, 19 mm (inner diameter) × 150 mm (length), manufactured by Waters). Water / methanol was used as a mobile phase for elution of the column, and gradient elution was performed to linearly increase the methanol concentration from 30% by volume to 100% by volume at a flow rate of 10 mL per minute for 15 minutes. Fractions eluted during a retention time of 5.2 to 6.5 minutes were collected and concentrated to complete dryness at 30 ° C. under reduced pressure using a rotary evaporator. The obtained dried product was dissolved in a small amount of acetonitrile and injected into a reverse phase column for HPLC (Sunfire prep C18, 10 mm (inner diameter) × 150 mm (length), manufactured by Waters). A mixture containing water and acetonitrile in a volume ratio of 60:40 was used as a mobile phase for elution of the column, and the mixture was passed at a flow rate of 1 mL per minute to obtain a fraction containing lorolide and epipyrrolide. As a result, 26 mg of Loriolide and 20 mg of Epyrroliolide were obtained as products.
［実施例２］
＜ロリオライド２４時間処理のナミハダニ産卵数に対する防除効果の検定＞
適量のロリオライドを、メタノールに添加して均一になるまで攪拌することにより、ロリオライドの濃度が１００ｍＭの薬剤濃縮溶液を調製した。ロリオライドは、製造例１で精製されたものを用いた。この薬剤濃縮溶液を、水によって最終濃度１、１０、１００、５００μＭになるよう希釈した。なお、対照区として０．１容量％メタノールのみを含む水溶液（０μＭ）を調製した。
[Example 2]
<Test of control effect on the number of spider mite spawned by Lorio Ride 24 hours>
An appropriate amount of Loriolide was added to methanol and stirred until uniform, thereby preparing a concentrated drug solution having a concentration of Loriolide of 100 mM. Loriolide used was purified in Production Example 1. This drug concentrated solution was diluted with water to a final concentration of 1, 10, 100, 500 μM. As a control, an aqueous solution (0 μM) containing only 0.1% by volume of methanol was prepared.
次いで、３〜４週齢のトマト葉の第３、４、５位葉を、各濃度のロリオライド希釈液に浸漬し、２５℃±１℃の恒温室内に置いた。２４時間後、トマト葉を蒸留水で洗い、風乾した後、実施例１に記載の方法に従って３０頭のナミハダニ雌成虫を接種し、同じ栽培条件下で栽培した。５日後に、トマト葉に産下された卵の数を計測した。
図２に、トマトにおけるナミハダニ産卵数に対する精製したロリオライドの２４時間処理の効果を示す。１００μＭ及び５００μＭのロリオライド希釈液で処理したトマト葉では、０．１容量％メタノールのみを処理した対照区と比較して、ナミハダニ産卵数の低下が認められた。
Subsequently, the 3rd, 4th, and 5th leaves of 3 to 4 week-old tomato leaves were immersed in a dilute solution of each concentration of Loriolide and placed in a thermostatic chamber at 25 ° C ± 1 ° C. After 24 hours, the tomato leaves were washed with distilled water and air-dried, then inoculated with 30 adult female spider mites according to the method described in Example 1, and cultivated under the same cultivation conditions. After 5 days, the number of eggs laid on the tomato leaves was counted.
FIG. 2 shows the effect of 24-hour treatment with purified loriolide on the number of spider mite eggs in tomato. In the tomato leaves treated with the 100 μM and 500 μM Loriolide dilutions, the number of spider mite spawning was reduced compared to the control group treated with only 0.1% by volume methanol.
［実施例３］
＜ロリオライド２４時間処理のナミハダニ生存数に対する防除効果の検定＞
３〜４週齢のトマト葉の第３、４、５位葉を、実施例２で調製した各濃度のロリオライド希釈液に浸漬し、２５℃±１℃の恒温室内に置いた。２４時間後、トマト葉を蒸留水で洗い、風乾した後、実施例１に記載の方法に従って３０頭のナミハダニ雌成虫を接種し、同じ栽培条件下で栽培した。５日後に、成虫の生死を判定し、生存数を計測した。
図３に、トマトにおけるナミハダニ生存数に対する精製したロリオライドの２４時間処理の効果（ナミハダニ雌成虫の生存率）を示す。５００μＭのロリオライド希釈液で処理したトマト葉では、０．１容量％メタノールのみを処理した対照区と比較して、ナミハダニ生存数の低下が認められた。
[Example 3]
<A test of the control effect on the number of surviving spider mites of Lorioride 24 hours>
The 3rd, 4th, and 5th tomato leaves of 3 to 4 weeks old were dipped in each concentration of Loriolide diluted solution prepared in Example 2 and placed in a thermostatic chamber at 25 ° C ± 1 ° C. After 24 hours, the tomato leaves were washed with distilled water and air-dried, then inoculated with 30 adult female spider mites according to the method described in Example 1, and cultivated under the same cultivation conditions. Five days later, the life and death of adults were determined, and the number of survivors was counted.
FIG. 3 shows the effect of 24-hour treatment with purified Loriolide (viability of adult female spider mite) on the number of surviving spider mites in tomato. In the tomato leaves treated with the 500 μM Loriolide dilution, a decrease in the number of surviving spider mites was observed compared to the control group treated with only 0.1% by volume of methanol.
［実施例４］
＜エピロリオライド２４時間処理のナミハダニ産卵数に対する防除効果の検定＞
適量のエピロリオライドを、メタノールに添加して均一になるまで攪拌することにより、エピロリオライドの濃度が１００ｍＭの薬剤濃縮溶液を調製した。エピロリオライドは、製造例１で精製されたものを用いた。この薬剤濃縮溶液を、水によって最終濃度１、１０、１００、３００μＭになるよう希釈した。なお、対照区として０．１容量％メタノールのみを含む水溶液（０μＭ）を調製した。
[Example 4]
<Test of the control effect on the number of spider mite spawned by Epiroliolide 24 hours>
An appropriate amount of pyrroliolide was added to methanol and stirred until uniform, thereby preparing a drug concentrated solution having an eproliolide concentration of 100 mM. The epipyrrolide used was purified in Production Example 1. This drug concentrated solution was diluted with water to a final concentration of 1, 10, 100, 300 μM. As a control, an aqueous solution (0 μM) containing only 0.1% by volume of methanol was prepared.
次いで、３〜４週齢のトマト葉の第３、４、５位葉を、各濃度のエピロリオライド希釈液に浸漬し、２５℃±１℃の恒温室内に置いた。２４時間後、トマト葉を蒸留水で洗い、風乾した後、実施例１に記載の方法に従って３０頭のナミハダニ雌成虫を接種し、同じ栽培条件下で栽培した。５日後に、トマト葉に産下された卵の数を計測した。
図４に、トマトにおけるナミハダニ産卵数に対する精製したエピロリオライドの２４時間処理の効果を示す。１０μＭ及び３００μＭのエピロリオライド希釈液で処理したトマト葉では、０．１容量％メタノールのみを処理した対照区と比較して、ナミハダニ産卵数の低下が認められた。実施例２の結果と比較したところ、エピロリオライドはロリオライドとほぼ同等の防除活性を示した。
Subsequently, the 3rd, 4th, and 5th leaves of 3 to 4 week-old tomato leaves were immersed in a dilution solution of each concentration of pyrroliolide and placed in a thermostatic chamber at 25 ° C ± 1 ° C. After 24 hours, the tomato leaves were washed with distilled water and air-dried, then inoculated with 30 adult female spider mites according to the method described in Example 1, and cultivated under the same cultivation conditions. After 5 days, the number of eggs laid on the tomato leaves was counted.
FIG. 4 shows the effect of 24-hour treatment with purified Epyrroliolide on the number of spider mite eggs laid in tomato. In the tomato leaves treated with the 10 μM and 300 μM eproliolide dilutions, a decrease in the number of spider mite spawning was observed compared to the control group treated with only 0.1% by volume methanol. When compared with the results of Example 2, Epyrrolide showed almost the same control activity as Loriolide.
［実施例５］
＜ロリオライドの殺ハダニ活性の検定＞
実施例２で調製したロリオライドの濃度が１００ｍＭの薬剤濃縮溶液を、水によって最終濃度１０００μＭになるよう希釈した。なお、対照区として０．１容量％メタノールのみを含む水溶液（０μＭ）を調製した。
[Example 5]
<A test of spider mite killing activity of Lorio Ride>
The drug-concentrated solution having a concentration of 100 mM of Loriolide prepared in Example 2 was diluted with water to a final concentration of 1000 μM. As a control, an aqueous solution (0 μM) containing only 0.1% by volume of methanol was prepared.
次いで、インゲンマメの葉片（１ｃｍ×１ｃｍ）に３日齢のナミハダニ雌成虫を載せ、５秒間、ロリオライド溶液中に完全に浸漬させた。風乾後、別途用意したインゲンマメ葉に浸漬処理したナミハダニを載せ、その葉を予め水を含ませた脱脂綿上に置き、２５℃±１℃、１５時間明期／９時間暗期条件下で制御した恒温室内に置いた。４８時間後、成虫の生死を判定し、生存数を計測した。１区当たり３０頭のナミハダニを用いた。
図５に、ナミハダニ生存数に対するロリオライド浸漬処理の効果を示す。ロリオライド処理区と対照区でナミハダニの生存数に差は認められなかったことから、ロリオライドは直接の殺ハダニ活性は有さないことが示された。
Next, a three-day-old adult female spider mite was placed on a leaf bean leaf piece (1 cm × 1 cm) and completely immersed in the Loriolide solution for 5 seconds. After air-drying, place a spider mite dipped in separately prepared kidney bean leaves, place the leaves on absorbent cotton soaked in advance, and control under conditions of 25 ° C ± 1 ° C, 15 hours light period / 9 hours dark period Placed in a constant temperature room. After 48 hours, the viability of adults was determined and the number of survivors was counted. 30 nymph mites per ward were used.
FIG. 5 shows the effect of the Loriolide soaking treatment on the number of surviving spider mites. There was no difference in the number of survivors of the spider mite between the loriolide-treated group and the control group, indicating that loriolide has no direct spidericide activity.
［実施例６］
＜ロリオライド２４時間処理のハスモンヨトウ生存数に対する防除効果の検定＞
実施例２で調製したロリオライドの濃度が１００ｍＭの薬剤濃縮溶液を、水によって最終濃度１、１０、１００、３００μＭになるよう希釈した。なお、対照区として０．１容量％メタノールのみを含む水溶液（０μＭ）を調製した。
[Example 6]
<A test of the control effect on the number of survivors of Lorio ride 24 hours>
The drug concentrated solution having a concentration of 100 mM Loriolide prepared in Example 2 was diluted to a final concentration of 1, 10, 100, and 300 μM with water. As a control, an aqueous solution (0 μM) containing only 0.1% by volume of methanol was prepared.
次いで、３〜４週齢のトマト葉の第３、４、５位葉を、各濃度のロリオライド希釈液に浸漬し、２５℃±１℃の恒温室内に置いた。２４時間後、トマト葉を蒸留水で洗い、風乾した後、葉柄を予め蒸留水を満たした１．５ｍＬ容チューブに入れ、水分の蒸発を防ぐためにパラフィルムで上部開口部を覆った後、これらのチューブを円柱形プラスチック容器（１４ｃｍ（直径）×６．５ｃｍ（高さ））に置き、葉１組あたり１０頭のハスモンヨトウ孵化幼虫を葉面上に載せ、実施例１に記載と同じ栽培条件で栽培した。５日後に、幼虫の生死を判定し、生存数を計測した。葉２枚を１組として、１処理区あたり１０組を検定に供した。
図６に、トマトにおけるハスモンヨトウ生存数に対する精製したロリオライドの２４時間処理の効果（ハスモンヨトウの生存率）を示す。１０μＭ以上の濃度のロリオライド希釈液で処理したトマト葉では、０．１容量％メタノールのみを処理した対照区と比較して、ハスモンヨトウ生存数の低下が認められた。
Subsequently, the 3rd, 4th, and 5th leaves of 3 to 4 week-old tomato leaves were immersed in a dilute solution of each concentration of Loriolide and placed in a thermostatic chamber at 25 ° C ± 1 ° C. After 24 hours, the tomato leaves were washed with distilled water and air-dried, and then the petiole was placed in a 1.5 mL tube pre-filled with distilled water, and the upper opening was covered with parafilm to prevent moisture evaporation. Are placed in a cylindrical plastic container (14 cm (diameter) x 6.5 cm (height)), and 10 scallop hatched larvae are placed on the leaf surface per pair of leaves. The same cultivation conditions as described in Example 1 Cultivated in After 5 days, the larvae were judged to be alive or dead, and the number of survivors was counted. Two sets of leaves were used as one set, and 10 sets per treatment group were subjected to the test.
FIG. 6 shows the effect of 24-hour treatment with purified Loriolide on the number of surviving lotus roots in tomatoes (survival rate of lotus roots). In the tomato leaves treated with the loriolide diluent having a concentration of 10 μM or more, a decrease in the survival number of the Japanese pearl moth was observed as compared with the control group treated with only 0.1% by volume of methanol.
[比較例１]
＜ジヒドロアクチニオディオライド２４時間処理のナミハダニ産卵数に対する防除効果の検定＞
ロリオライドの類縁化合物であるジヒドロアクチニオディオライド処理による防除効果を、実施例２に記載の方法に準じて行った。ジヒドロアクチニオディオライドは、下記式（３）で表される化合物である。検定においては、最終濃度１００、５００、又は、７００μＭのジヒドロアクチニオディオライド（Ark Pharm社製）及び０．１容量％メタノールを含む水溶液にトマト葉を浸漬した後、当該トマト葉にナミハダニ雌成虫を接種し、トマト葉に産下された卵の数を計測した。なお、０．１容量％メタノール水溶液で処理したトマト葉を対照とした。
ジヒドロアクチニオディオライドでトマト葉を処理した全ての場合において、ナミハダニの産卵数と対照における産卵数との間に有意差がなかった。この結果は、ロリオライドが有する防除効果にとってロリオライドの３位の水酸基の存在が重要であることを示している。
[Comparative Example 1]
<A test of the control effect on the number of spider mite spawning treated with dihydroactiniodiolide 24 hours>
The control effect by treatment with dihydroactiniolide, which is a related compound of Loriolide, was performed according to the method described in Example 2. Dihydroactinioride is a compound represented by the following formula (3). In the assay, tomato leaves were dipped in an aqueous solution containing dihydroactinidiolide (Ark Pharm) at a final concentration of 100, 500, or 700 μM and 0.1% by volume methanol, and then adult nymph mite on the tomato leaves. And the number of eggs laid on tomato leaves was counted. In addition, the tomato leaf processed with 0.1 volume% methanol aqueous solution was set as the control.
In all cases where tomato leaves were treated with dihydroactiniodiolide, there was no significant difference between the number of spider mite spawning and the number of spawning in the control. This result shows that the presence of the hydroxyl group at the 3-position of Loriolide is important for the control effect of Loriolide.
本発明に係る害虫抵抗性誘導剤及びこれを用いた植物の害虫防除方法は、虫害、特に食害や吸汁害に対して有効であり、かつ抵抗性系統を出現させるおそれが非常に小さく、また、従来の農薬よりも環境や人体への安全性も高い。このため、本発明に係る害虫抵抗性誘導剤及びこれを用いた植物の害虫防除方法は、特に農作物や観葉植物の栽培、中でも、ナス科植物及びアブラナ科植物の栽培等の分野において好適に使用できる。 The pest resistance inducer according to the present invention and the plant pest control method using the pest resistance inducer are effective against insect damage, particularly eating damage and sucking damage, and have a very low risk of causing resistance lines. It is safer for the environment and the human body than conventional agricultural chemicals. Therefore, the pest resistance inducer according to the present invention and the plant pest control method using the same are preferably used in fields such as cultivation of crops and foliage plants, especially cultivation of solanaceous plants and cruciferous plants. it can.
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