JP6706949B2 - Adventitious root development inducer and root system development promoter - Google Patents
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本発明は、植物の不定根の発生誘導剤及び根系発達促進剤に関する。 TECHNICAL FIELD The present invention relates to an adventitious root development inducer and root system development promoter of plants.
農業分野において、植物の成長を制御することは生産性向上のために重要な技術である。現在では植物の成長調節を目的とした様々な種類の植物成長調整剤が実用化され、植物成長調整剤は作物の収量や生産物の品質向上に貢献している。その中でも根は植物の定着、吸水、養分吸収、倒伏防止など非常に重要な役割を担っているため、その発達を促進することは重要である。
植物の根は、主根、側根、不定根によって構成され、これらを合わせて根系と呼ばれている。主根は種子の段階で既に発達しており、発芽と同時に伸長する。側根は主根から分化し発達する。また、不定根は茎や葉などといった根以外の組織から分化し、発達する。このため、植物の培養細胞から発生する根や、挿し木・挿し葉などの地上部の組織切片から発生する根は不定根に分類され、いわゆる栄養繁殖を効率よく進める上では不定根の発生を誘導することは重要な産業上の技術となっている。また、イネ科作物などの単子葉植物は、発芽後まもなく幼根の成長が停止し、種子根を除くほとんどの根は茎から発生する不定根であり、冠根とも呼ばれている。これらの不定根の発生を誘導することはイネ科植物の安定した生育を確保する上では重要である。特に主要な作物であるイネ、ムギ、トウモロコシなどの生育や倒伏防止にとって不定根発生は重要である。
In the agricultural field, controlling plant growth is an important technique for improving productivity. At present, various kinds of plant growth regulators for the purpose of controlling the growth of plants have been put into practical use, and the plant growth regulators contribute to the improvement of crop yield and the quality of products. Among them, roots play a very important role in plant fixation, water absorption, nutrient absorption, lodging prevention, etc., so it is important to promote their development.
The root of a plant is composed of a main root, a lateral root, and an adventitious root, and these are collectively called a root system. The main root is already developed at the seed stage and grows upon germination. Lateral roots differentiate and develop from main roots. In addition, adventitious roots differentiate and develop from tissues other than roots such as stems and leaves. For this reason, roots that arise from cultured cells of plants and roots that arise from tissue sections of the above-ground parts such as cuttings and cuttings are classified as adventitious roots, and in order to efficiently promote so-called vegetative propagation, induce adventitious roots. Has become an important industrial technology. In monocotyledonous plants such as grasses, the growth of radicles is stopped shortly after germination, and most of the roots except seed roots are adventitious roots generated from stems and are also called crown roots. Inducing the development of these adventitious roots is important for ensuring stable growth of grasses. Adventitious root development is particularly important for the growth and prevention of lodging of major crops such as rice, wheat and corn.
不定根発生誘導、根系発達促進作用を有する植物成長調整剤が望まれている。しかしながら、不定根の発生を誘導する植物成長調整剤は、その数が少なく、効果も十分でなく、更に好ましくない作用を有する場合が多かった。例えば、現在不定根発生剤として広く用いられているオーキシン系化合物は、植物の種類や状態、施用する濃度によっては植物に対して毒性を示し、茎や葉のクロロシス、枯死等といった好ましくない作用を及ぼすことがある。
特開２０１３−４７２２５号公報（特許文献１）にはジクロロフェニル基やジフロロフェニル基などを有する化合物がユーカリの不定根を発生させることが記載されている。また特開平５−２６０８６９号公報（特許文献２）にはオーキシンとしてα−ナフタリン酢酸を併用するとサツマイモの茎に不定根を誘導できることが記載されている。さらにまた特開平５−４９４８４号公報（特許文献３）にはレモンバームのカルスを、オーキシンを添加した培地中で培養して不定根の発生を誘導する技術が記載されている。
A plant growth regulator having an effect of inducing adventitious root development and promoting root system development is desired. However, the number of plant growth regulators that induce adventitious root generation is small, the effect is not sufficient, and moreover, there are many cases in which it has an unfavorable action. For example, auxin compounds, which are widely used as adventitious root generators, are toxic to plants depending on the type and condition of the plant and the concentration applied, and exert undesired effects such as chlorosis of stems and leaves and death. Sometimes.
Japanese Unexamined Patent Application Publication No. 2013-47225 (Patent Document 1) describes that a compound having a dichlorophenyl group, a difluorophenyl group or the like causes adventitious roots of Eucalyptus. Further, JP-A-5-260869 (Patent Document 2) describes that adventitious roots can be induced in sweet potato stems by using α-naphthaleneacetic acid as an auxin. Furthermore, JP-A-5-49484 (Patent Document 3) describes a technique for inducing the development of adventitious roots by culturing lemon balm callus in a medium containing auxin.
また、植物ホルモンの中でインドール酢酸は不定根や側根の発生を誘導することが知られている（非特許文献１）。その生合成経路をたどると、主要な前駆体はトリプトファンであり、さらにトリプトファンの前駆体の一つはアントラニル酸であることが知られている（非特許文献２）。
しかし、側根の発生誘導に関しては、ジャスモン酸を処理したシロイヌナズナではアントラニル酸合成酵素の発現が亢進し、結果的にインドール酢酸が蓄積する結果、側根の発生が誘導される（非特許文献３）が不定根の発生誘導作用についてはまったく報告がなく、逆にアントラニル酸そのものを植物に施用した場合には不定根の発生は誘導されないとされていた（非特許文献１参照）。
すなわち、上述のようにアントラニル酸はインドール酢酸の前駆体として考えられていたために、トリプトファンやインドール酢酸に変換されないかぎり不定根発生促進作用があるとは考えられなかった。さらにその誘導体はインドール酢酸に変換されないため、不定根発生誘導作用、根系発達誘導作用を有するとは理論上も考えられなかった。このことから、アントラニル酸誘導体は結果的にトリプトファン合成酵素活性を阻害するとされ、むしろ植物成長抑制物質として認識されていた（非特許文献２参照）。
In addition, among plant hormones, indoleacetic acid is known to induce the development of adventitious roots and lateral roots (Non-Patent Document 1). Following its biosynthetic pathway, it is known that the main precursor is tryptophan, and one of the tryptophan precursors is anthranilic acid (Non-Patent Document 2).
However, regarding the induction of lateral root development, in Arabidopsis treated with jasmonic acid, the expression of anthranilate synthase is enhanced, and as a result, indoleacetic acid accumulates, the development of lateral roots is induced (Non-Patent Document 3). There is no report on the adventitious root development-inducing action, and conversely, it was said that the adventitious root development was not induced when anthranilic acid itself was applied to plants (see Non-Patent Document 1).
That is, since anthranilic acid was considered as a precursor of indoleacetic acid as described above, it was not considered to have an adventitious root development promoting action unless it was converted to tryptophan or indoleacetic acid. Furthermore, since the derivative is not converted to indoleacetic acid, it was theoretically not considered to have adventitious root development inducing action or root system development inducing action. From this, it is considered that the anthranilic acid derivative eventually inhibits the activity of tryptophan synthase, and it was rather recognized as a plant growth inhibitor (see Non-Patent Document 2).
本発明の課題は、植物の不定根発生誘導剤及び根系発達促進剤を提供することである。 An object of the present invention is to provide a plant adventitious root development inducer and a root system development promoter.
本発明者らは、上記課題を解決するために鋭意研究した結果、従来不定根発生誘導作用がないものと考えられているアントラニル酸アミド誘導体が不定根の発生を誘導し、さらに根系の発達を促進させることを見出した。そしてこの作用は、アントラニル酸の誘導体にも存在する。本出願人は、これをＰＣＴ／ＪＰ２０１５／０７４３３５として特許出願を行っている。そしてさらに研究を進めた結果、新たに、アントラニル酸の４位の位置がアミド化された骨格を有する化合物が強い不定根の発生作用とオーキシン類による不定根発生作用を増強することを見いだし、本発明を完成するに至った。 The present inventors, as a result of intensive research to solve the above problems, an anthranilic acid amide derivative, which is conventionally considered to have no adventitious root development inducing action, induces adventitious root development and further promotes root system development. I found that. And this effect also exists in the derivative of anthranilic acid. The present applicant has filed a patent application as PCT/JP2015/074335. As a result of further research, it was discovered that a compound having a skeleton in which the 4-position of anthranilic acid is amidated enhances the strong adventitious root-generating action and the adventitious root-generating action by auxins, and the present invention It came to completion.
すなわち、本発明は、以下の構成からなる。
１．下記の（式１）であらわされる化合物もしくはその塩またはエステル体からなる、植物の不定根発生誘導剤及び根系発達促進剤。
That is, the present invention has the following configurations.
1. A plant adventitious root development inducer and a root system development promoter comprising a compound represented by the following (Formula 1) or a salt or ester thereof.
２．Ｒ１の直鎖又は分岐鎖のアルキル基がメチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｔ−ブチル基、ペンチル基のいずれかであり、環状飽和炭化水素基がシクロヘキシル基である１に記載の、植物の不定根発生誘導剤又は根系発達促進剤。
３．Ｒ２のエーテル結合した直鎖のアルキル基がメチル基である１に記載の、植物の不定根発生誘導剤又は根系発達促進剤。
４．不定根を発生させようとする植物体に直接散布する形態である１〜３のいずれかに記載の植物の不定根発生誘導剤又は根系発達促進剤。
５．１〜４のいずれかに記載の植物の不定根発生誘導剤又は根系発達促進剤を含有する肥料。
６．１〜４のいずれかに記載の植物の不定根発生誘導剤又は根系発達促進剤を含有する農薬。
2. The linear or branched alkyl group of R1 is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, or a pentyl group, and the cyclic saturated hydrocarbon group is a cyclohexyl group. 1. The plant adventitious root development inducer or root system development promoter according to 1.
3. 2. The plant adventitious root development inducer or root system development accelerator according to 1, wherein the ether- bonded linear alkyl group of R2 is a methyl group.
4. The adventitious root development inducer or root system development promoter according to any one of 1 to 3, which is a form in which the adventitious root is directly sprayed onto a plant body.
A fertilizer containing the adventitious root development inducer or root system development promoter of any one of 5.1 to 4.
6. A pesticide containing the adventitious root development inducer or root system development promoter according to any one of claims 1 to 4.
本発明により、新規な植物の不定根発生誘導剤及び根系発達促進剤が提供される。本発明の植物の不定根発生誘導剤及び根系発達促進剤は、不定根誘導活性が高く、かつ茎や葉のクロロシスといった副作用が極めて弱い。本発明の植物の不定根発生誘導剤及び根系発達促進剤は挿し木時・育苗期・移植時の不定根発生促進剤として有用である。また、イネ科植物の冠根は不定根であるため、イネ科の冠根発生促進剤としても作用し、倒伏防止にも有用である。また根系発達を促進するため、肥料成分の吸収効率が向上し、植物の生育を促進する。さらに本発明の剤を育苗に用いると、より根張りの良い生育の良い健康な苗を生産することができる。 The present invention provides a novel plant adventitious root development inducer and root system development promoter. The adventitious root development inducer and root system development promoter of the present invention have a high adventitious root inducing activity and have extremely weak side effects such as chlorosis of stems and leaves. The adventitious root development inducer and root system development promoter of the present invention are useful as adventitious root development promoters during cutting, seedling raising and transplantation. In addition, since the crown roots of grasses are adventitious roots, they also act as crown root development promoters of grasses and are useful for preventing lodging. In addition, since it promotes root system development, it improves absorption efficiency of fertilizer components and promotes plant growth. Further, when the agent of the present invention is used for raising seedlings, healthy seedlings with better rooting and good growth can be produced.
本発明の植物の不定根発生誘導剤及び根系発達促進剤は、（式１）であらわされる化合物もしくはその塩またはエステル体を有効成分としている。 The adventitious root development inducer and root system development promoter of the present invention contain the compound represented by (Formula 1) or a salt or ester thereof as an active ingredient.
上記化学式の化合物は、アントラニル酸の４−アミド化合物の骨格を有する化合物である。
上記（式１）の置換基であるＲ１は、水素原子、炭素数１〜６の直鎖又は分岐鎖アルキル基、環状飽和炭化水素基であって、−（ＣＨ２）１〜5−ＣＨ３、−ＣＨ（ＣＨ３）２、−Ｃ（ＣＨ３）３、−Ｃ６Ｈ１１の構造を有する置換基から選択されるいずれかであることが好ましい。
The compound represented by the above chemical formula is a compound having a skeleton of a 4-amide compound of anthranilic acid.
It said R1 is a substituent of formula (1) is a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, a cyclic saturated hydrocarbon group, - (CH 2) 1~5 -CH 3 , -CH (CH 3) 2, -C (CH 3) 3, is preferably any one selected from a substituent having the structure -C 6 H 11.
Ｒ２は、水酸基又はエーテル基であり、エーテル基は−ＯＣＨ３であることが好ましい。 R2 is a hydroxyl group or an ether group, is preferably an ether group is -OCH 3.
（式１）で表される化合物の塩としては、例えばナトリウム塩、カリ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、アンモニウム塩等の無機塩基塩類、トリエチルアミン塩、ピリジン塩、ピコリン塩、エタノールアミン塩、トリエタノールアミン塩、ジシクロヘキシルアミン塩、又はＮ，Ｎ’−ジベンジルエチレンジアミン塩の有機アミン塩等の有機塩基塩類が挙げられる。
また、塩酸塩、硫酸塩、硝酸塩等の無機酸塩、蟻酸塩、酢酸塩、プロピオン酸塩、酪酸塩、乳酸塩等の有機酸塩等の塩が挙げられる。
Examples of the salt of the compound represented by (Formula 1) include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, inorganic base salts such as ammonium salt, triethylamine salt, Examples thereof include organic base salts such as pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt, and organic amine salt of N,N′-dibenzylethylenediamine salt.
Further, inorganic acid salts such as hydrochlorides, sulfates and nitrates, salts such as organic acid salts such as formate salts, acetate salts, propionate salts, butyrate salts and lactate salts can be mentioned.
（式１）で表される化合物のエステルとしては低級アルキルエステルを挙げることができる。 Examples of the ester of the compound represented by (Formula 1) include lower alkyl ester.
（式１）で示される化合物で有用な化合物の一例として次の物質を例示できる。また必要に応じて合成することができる。
Ｒ１がアルキル基または環状飽和炭化水素基、Ｒ２がメトキシ基である化合物の合成は、２−アミノテレフタル酸１−メチルを出発物質として、各種のＲ１に対応する置換基を有するアミンを常法によりアミド結合を形成させることにより合成することができる。
Ｒ２が水酸基である化合物の合成は、上記のメチルエステルを加水分解することによって得ることができる。加水分解法としては、アルカリ加水分解、酸加水分解、酵素処理などを用いることができるが、操作が簡便であることからアルカリ加水分解が好ましい。
またＲ２の置換基がメチル基以外のエーテル基を有する化合物は、２−アミノテレフタル酸１−メチルから合成したＲ２がメトキシ基である化合物や、さらに加水分解することによって合成したＲ２が水酸基である化合物を、エステル化やエステル交換などの常法により得ることができる。
The following substances can be illustrated as an example of the compound useful as the compound represented by (Formula 1). Further, they can be synthesized as needed.
Synthesis of a compound in which R1 is an alkyl group or a cyclic saturated hydrocarbon group and R2 is a methoxy group is carried out using 1-methyl 2-aminoterephthalate as a starting material and various amines having substituents corresponding to R1 by a conventional method. It can be synthesized by forming an amide bond.
The compound in which R2 is a hydroxyl group can be obtained by hydrolyzing the above methyl ester. As the hydrolysis method, alkali hydrolysis, acid hydrolysis, enzyme treatment and the like can be used, but alkali hydrolysis is preferred because the operation is simple.
Further, the compound in which the substituent of R2 has an ether group other than a methyl group is a compound in which R2 synthesized from 1-methyl 2-aminoterephthalate is a methoxy group, or R2 synthesized by further hydrolysis is a hydroxyl group. The compound can be obtained by a conventional method such as esterification or transesterification.
なお、反応終了後、反応液から生成物を採取するには、反応溶媒を留去し、水と混合しない生成物可溶性有機溶媒と水を加え、適宜水相のｐＨを調整後、溶媒抽出を行い、有機溶媒層を回収後、乾燥し、有機溶媒を留去した後、必要に応じて単一もしくは混合溶媒から再結晶すればよい。また、必要に応じて高速液体クロマトグラフィー（ＨＰＬＣ）などの分離手段によって単離すればよい。 After the completion of the reaction, in order to collect the product from the reaction solution, the reaction solvent is distilled off, a product-soluble organic solvent that is immiscible with water and water are added, and the pH of the aqueous phase is appropriately adjusted, followed by solvent extraction. After the organic solvent layer is collected, the organic solvent layer is dried, the organic solvent is distilled off, and then recrystallized from a single solvent or a mixed solvent, if necessary. Further, it may be isolated by a separation means such as high performance liquid chromatography (HPLC), if necessary.
本発明における植物の不定根発生誘導剤及び根系発達促進剤として有用な代表的化合物名称及び化学式を次に例示する。当然本発明は、これらの化合物に限定されるものではない。 Representative compound names and chemical formulas useful as the adventitious root development inducer and root system development promoter of the present invention are shown below. Naturally, the invention is not limited to these compounds.
化合物１
２−アミノ−４−［（メチルアミノ）カルボニル］−安息香酸（２−Ａｍｉｎｏ−４−［（ｍｅｔｈｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏｉｃ ａｃｉｄ）
2-Amino-4-[(methylamino)carbonyl]-benzoic acid (2-Amino-4-[(methylamino)carbonyl]-benzoic acid)
化合物２
メチル ２−アミノ−４−［（イソプロピルアミノ）カルボニル］−安息香酸 （Ｍｅｔｈｙｌ ２−Ａｍｉｎｏ−４−［（ｉｓｏｐｒｏｐｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏａｔｅ）
Methyl 2-Amino-4-[(isopropylamino)carbonyl]-benzoic acid (Methyl 2-Amino-4-[(isopropylamino)carbonyl]-benzoate)
化合物３
２−アミノ−４−［（イソプロピルアミノ）カルボニル］−安息香酸 （２−Ａｍｉｎｏ−４−［（ｉｓｏｐｒｏｐｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏｉｃ ａｃｉｄ）
2-Amino-4-[(isopropylamino)carbonyl]-benzoic acid (2-Amino-4-[(isopropylamino)carbonyl]-benzoic acid)
化合物４
２−アミノ−４−［（ｔ−ブチルアミノ）カルボニル］−安息香酸（２−Ａｍｉｎｏ−４−［（ｔｅｒｔ−ｂｕｔｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏｉｃ ａｃｉｄ）
2-Amino-4-[(t-butylamino)carbonyl]-benzoic acid (2-Amino-4-[(tert-butylamino)carbonyl]-benzoic acid)
化合物５
メチル ２−アミノ−４−［（ブチルアミノ）カルボニル］−安息香酸（Ｍｅｔｈｙｌ ２−Ａｍｉｎｏ−４−［（ｂｕｔｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏａｔｅ）
Methyl 2-amino-4-[(butylamino)carbonyl]-benzoic acid (Methyl 2-Amino-4-[(butylamino)carbonyl]-benzoate)
化合物６
２−アミノ−４−［（ブチルアミノ）カルボニル］−安息香酸（２−Ａｍｉｎｏ−４−［（ｂｕｔｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏｉｃ ａｃｉｄ）
2-Amino-4-[(butylamino)carbonyl]-benzoic acid (2-Amino-4-[(butylamino)carbonyl]-benzoic acid)
化合物７
２−アミノ−４−［（シクロヘキシルアミノ）カルボニル］−安息香酸（２−Ａｍｉｎｏ−４−［（ｃｙｃｌｏｈｅｘｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏｉｃ ａｃｉｄ）
2-Amino-4-[(cyclohexylamino)carbonyl]-benzoic acid (2-Amino-4-[(cyclohexylamino)carbonyl]-benzoic acid)
化合物８
２−アミノ−４−［（ヘキシルアミノ）カルボニル］−安息香酸（２−Ａｍｉｎｏ−４−［（ｈｅｘｙｌａｍｉｎｏ）ｃａｒｂｏｎｙｌ］−ｂｅｎｚｏｉｃ ａｃｉｄ）
2-Amino-4-[(hexylamino)carbonyl]-benzoic acid (2-Amino-4-[(hexylamino)carbonyl]-benzic acid)
本発明の植物の不定根発生誘導剤及び根系発達促進剤は、複数の活性作用をもつ化合物を２種以上組み合わせ、使用することもできる。またオーキシンなどの植物ホルモン剤と併用することも可能である。 The adventitious root development inducer and root system development promoter of the present invention may be used in combination of two or more compounds having a plurality of active actions. It is also possible to use it in combination with a plant hormone agent such as auxin.
本発明の植物の不定根発生誘導剤及び根系発達促進剤は、（式１）〜（式９）の化合物の水溶液をそのまま植物の不定根発生誘導剤及び根系発達促進剤として用いることができるが、水和剤、乳剤、粒剤、粉剤、界面活性剤など、通常の植物成長調整剤で用いられる担体を用いて製剤化してもよい。例えば、固体担体としては鉱物質粉末（カオリン、ベントナイト、クレー、モンモリロナイト、タルク、ケイソウ土、雲母、バーミキュライト、セッコウ、炭酸カルシウム、リン石灰など）、植物質粉末（大豆粉、小麦粉、木粉、タバコ粉、デンプン、結晶セルロースなど）、高分子化合物（石油樹脂、ポリビニルアルコール樹脂、ポリビニル酢酸樹脂、ポリ塩化ビニル、ケトン樹脂など）、更に、アルミナ、ワックス類などを使用することができる。また、液体担体としては、例えば、アルコール類（メタノール、エタノール、プロパノール、ブタノール、エチレングリコール、ベンジルアルコールなど）、芳香族炭化水素類（トルエン、ベンゼン、キシレンなど）、塩素化炭化水素類（クロロホルム、四塩化炭素、モノクロルベンゼンなど）、エーテル類（ジオキサン、テトラヒドロフランなど）、ケトン類（アセトン、メチルエチルケトンなど）、エステル類（酢酸エチル、酢酸ブチルなど）、酸アミド類（Ｎ，Ｎ−ジメチルアセトアミドなど）、エーテルアルコール類（エチレングリコールエチルエーテルなど）、又は水などを使用することができる。 As for the adventitious root development inducer and root system development promoter of the present invention, an aqueous solution of the compound of (Formula 1) to (Formula 9) can be used as it is as a plant adventitious root development inducer and root system development promoter. You may formulate using the carrier used with a normal plant growth regulator, such as a Japanese medicine, an emulsion, a granule, a powder, and a surfactant. For example, as a solid carrier, mineral powder (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, phospholime, etc.), vegetable powder (soybean flour, wheat flour, wood flour, tobacco) Powders, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl alcohol resin, polyvinyl acetate resin, polyvinyl chloride, ketone resin, etc.), as well as alumina, waxes and the like can be used. Examples of the liquid carrier include alcohols (methanol, ethanol, propanol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, etc.), chlorinated hydrocarbons (chloroform, Carbon tetrachloride, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, etc.), esters (ethyl acetate, butyl acetate, etc.), acid amides (N,N-dimethylacetamide, etc.) , Ether alcohols (such as ethylene glycol ethyl ether), or water can be used.
乳化、分散、拡散などの目的で使用される界面活性剤としては、非イオン性、陰イオン性、陽イオン性及び両イオン性のいずれも使用することができる。本発明において使用することができる界面活性剤の例を挙げると、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレン脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、オキシエチレンポリマー、オキシプロピレンポリマー、ポリオキシエチレンアルキルリン酸エステル、脂肪酸塩、アルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルリン酸塩、アルキルリン酸エステル塩、ポリオキシエチレンアルキル硫酸エステル、第四級アンモニウム塩、オキシアルキルアミン、レシチン、サポニン等である。また、必要に応じてゼラチン、カゼイン、アルギン酸ソーダ、デンプン、寒天、ポリビニルアルコールなどを補助剤として用いることができる。 As the surfactant used for the purpose of emulsification, dispersion, diffusion and the like, any of nonionic, anionic, cationic and amphoteric can be used. Examples of surfactants that can be used in the present invention include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, oxyethylene polymer. , Oxypropylene polymer, polyoxyethylene alkyl phosphate ester, fatty acid salt, alkyl sulfate ester salt, alkyl sulfonate, alkyl aryl sulfonate, alkyl phosphate, alkyl phosphate ester salt, polyoxyethylene alkyl sulfate ester, Quaternary ammonium salts, oxyalkylamines, lecithin, saponins and the like. If necessary, gelatin, casein, sodium alginate, starch, agar, polyvinyl alcohol, etc. can be used as an auxiliary agent.
本発明の植物の不定根発生誘導剤及び根系発達促進剤は、製剤の形状も制限はなく、粉剤、顆粒剤、粒剤、水和剤、フロアブル剤、乳剤及びペースト剤等のあらゆる製剤形態に成形することができる。その他の成分を常法に従い、混合、撹拌、噴霧乾燥等することにより製造することができる。
植物に適用する場合、土壌処理剤、茎葉処理剤、播種前の種子処理剤、移植前植物の処理剤及び移植時の植物に対する処理剤等として使用することができる。また、水耕栽培においては水耕液に混合して使用してもよく、組織培養では培地中に懸濁又は溶解させて用いてもよい。
本発明の植物の不定根発生誘導剤及び根系発達促進剤を目的の植物に適用すれば、側根数、不定根数などの根数の増加を通じて根量や根密度が増加するため、苗の移植時の活着率向上や、健苗育成、生育促進、吸水力の向上、吸肥力の向上、肥料成分利用率の向上、緑色の保持、光合成能力の向上、水ストレス耐性の向上、倒伏防止、収量増加等の効果が得られる。また、イネ科植物の登熱を向上させるので、イネ等の収量を向上させることができる。
The adventitious root development inducer and root system development promoter of the present invention are not limited in the shape of the preparation, and can be formed into any preparation form such as powder, granules, granules, wettable powders, flowables, emulsions and pastes. can do. It can be produced by mixing, stirring, spray drying and the like with other components according to a conventional method.
When applied to plants, it can be used as a soil treating agent, a foliage treating agent, a seed treating agent before sowing, a treating agent for plants before transplantation, a treating agent for plants at the time of transplantation and the like. Further, in hydroponics, it may be used as a mixture with a hydroponic solution, and in tissue culture, it may be used after being suspended or dissolved in a medium.
When the adventitious root development inducer and root system development promoter of the plant of the present invention is applied to a target plant, the number of lateral roots, the number of roots such as the number of adventitious roots and the density of the roots increase, so that when transplanting seedlings Improving survival rate, raising healthy seedlings, promoting growth, improving water absorption capacity, improving fertilizer absorption capacity, improving utilization rate of fertilizer components, maintaining green color, improving photosynthetic capacity, improving water stress resistance, preventing lodging, increasing yield, etc. The effect of is obtained. In addition, since the temperature of grasses is increased, the yield of rice and the like can be improved.
本発明の植物の不定根発生誘導剤及び根系発達促進剤を散布用として用いる場合の使用濃度は、好ましくは０．０１〜１００００ｐｐｍ、より好ましくは１〜５０００ｐｐｍ、特に好ましくは５〜１０００ｐｐｍの範囲とすることができる。特に育苗期の苗に使用する場合は、上記濃度の希釈液を培養土１Ｌ当たり５０〜２００ｍｌ散布することが望ましい。この場合、展着剤を使用してもよく、用いる展着剤の種類及び使用量については特に制限されない。また葉面散布しても効果を発揮する。
肥料と混合する場合を含め、土壌に直接施用する場合の使用量としては、１ヘクタール当たり１００〜１００００ｇ、特に５００〜５０００ｇ用いるのが好ましい。特に育苗期の苗に使用する場合は、培養土１Ｌ当たり０．００１〜１０ｇ用いるのが望ましい。この場合、播種前の培養土に予め混合しておいてもよく、育苗期間中に散布してもよい。
When using the adventitious root development inducer and root system development promoter of the plant of the present invention for spraying, the concentration used is preferably 0.01 to 10000 ppm, more preferably 1 to 5000 ppm, and particularly preferably 5 to 1000 ppm. be able to. Particularly when used for seedlings at the seedling raising stage, it is desirable to spray 50 to 200 ml of the diluted solution having the above concentration per 1 L of culture soil. In this case, a spreading agent may be used, and the type and amount of the spreading agent used are not particularly limited. Also effective when sprayed on leaves.
The amount used when directly applied to soil, including the case of mixing with fertilizer, is preferably 100 to 10000 g, and particularly preferably 500 to 5000 g per hectare. Particularly when used for seedlings in the seedling raising stage, it is desirable to use 0.001 to 10 g per 1 L of culture soil. In this case, it may be premixed with the culture soil before sowing, or may be sprayed during the seedling raising period.
播種前の種子処理用として用いる場合は、水、アルコール類（メタノール、エタノールなど）、ケトン類（アセトンなど）、芳香族炭化水素類（トルエン、ベンゼンなど）、塩素化炭化水素類（クロロホルム、塩化メチレンなど）、エーテル類（ジエチルエーテルなど）、エステル類（酢酸エチルなど）等の液体担体に０．０１〜１０００００ｐｐｍとなるように希釈し、乾燥種子に噴霧するか、乾燥種子を希釈液に浸漬して種子に吸収させることもできる。浸漬時間としては特に制限されないが１秒〜１２０分が好ましい。また、処理した種子は、風乾、減圧乾燥、加熱乾燥、真空乾燥などによって液体担体を蒸発させてもよい。クレーなどの鉱物質粉末の固体担体を用いて製剤化したものを種子表面に付着させ使用することもできる。通常用いられている種子コーティング剤、種子コーティングフィルムに混合して種子に被覆することもできる。
組織培養や細胞培養時に使用する場合は、通常用いられる植物組織培養用の培地（ＭＳ培地、ホワイト培地、ガンボルグのＢ５培地など）に培地中濃度として、好ましくは０．０１〜１００００ｐｐｍ、特に好ましくは０．１〜１０００ｐｐｍの範囲で溶解又は懸濁して用いることができる。この場合、通常行われているように、炭素源としての糖類（ショ糖、ブドウ糖など）、各種植物ホルモンとしてサイトカイニン（ベンジルアデニン、カイネチンなど）、オーキシン（インドール酢酸、ナフタレン酢酸など）、ジベレリン（ＧＡ３、ＧＡ４など）、アブシジン酸などを適宜加えることができる。
移植前の植物に直接吸収させる場合は、使用濃度として０．１〜１０００ｐｐｍに希釈又は懸濁した液に、植物の根部あるいは全体を浸漬して使用することができる。また、挿し穂、挿し芽、挿し木などであれば基部又は全体を浸漬して使用することができる。この場合の浸漬時間は１秒〜１週間、特に１分〜３日間が望ましい。鉱物質粉末の固体担体を用いて製剤化したものを、根部に付着させたり、挿し穂、挿し芽、挿し木などの場合は茎基部に付着させてもよい。
本発明の植物の不定根発生誘導剤及び根系発達促進剤の投与時期としては、生育期間中いかなる時期にも使用が可能であるが、特に不定根発生誘導剤、根系発達促進剤として適用する場合は、播種前、播種時、苗の育成時、移植等の耕種的断根を伴う作業の前後、気象要因などで根の発育が阻害されあるいは根に障害が発生した場合などが特に有効である。
When used for seed treatment before sowing, water, alcohols (methanol, ethanol, etc.), ketones (acetone, etc.), aromatic hydrocarbons (toluene, benzene, etc.), chlorinated hydrocarbons (chloroform, chloride, etc.) Dilute to 0.01 to 100000ppm in a liquid carrier such as methylene, etc.), ethers (diethyl ether, etc.), esters (ethyl acetate, etc.) and spray on dry seeds or dip dry seeds in a diluting solution. It can also be absorbed by seeds. The immersion time is not particularly limited, but 1 second to 120 minutes is preferable. Further, the treated seeds may be subjected to air drying, reduced pressure drying, heat drying, vacuum drying or the like to evaporate the liquid carrier. It is also possible to use a product prepared by using a solid carrier of mineral powder such as clay, which is adhered to the seed surface and used. It is also possible to mix the seed coating agent or seed coating film that is commonly used to coat the seed.
When used in tissue culture or cell culture, a medium for plant tissue culture that is usually used (MS medium, white medium, B5 medium of Gamborg, etc.), as a medium concentration, preferably 0.01 to 10,000 ppm, particularly preferably It can be used by being dissolved or suspended in the range of 0.1 to 1000 ppm. In this case, sugars (sucrose, glucose, etc.) as carbon sources, cytokinins (benzyl adenine, kinetin, etc.) as various plant hormones, auxins (indole acetic acid, naphthalene acetic acid, etc.), gibberellin (GA3) , GA4, etc.), abscisic acid, etc. can be added as appropriate.
When directly absorbed into a plant before transplantation, the root part or the whole of the plant can be immersed in a solution diluted or suspended to a working concentration of 0.1 to 1000 ppm for use. In addition, for cuttings, cuttings, cuttings, etc., the base or the whole can be immersed and used. In this case, the immersion time is preferably 1 second to 1 week, particularly 1 minute to 3 days. A product prepared by using a solid carrier of a mineral powder may be attached to the root part or, in the case of cuttings, cuttings, cuttings, etc., attached to the stem base.
The administration time of the adventitious root development inducer and root system development promoter of the plant of the present invention, it is possible to use at any time during the growth period, especially when applied as an adventitious root development inducer, root system development promoter, It is particularly effective before seeding, at seeding, during seedling growth, before and after work involving agronomic rooting such as transplantation, or when root development is impaired or root damage occurs due to weather factors.
本発明の植物の不定根発生誘導剤及び根系発達促進剤の適用対象となる植物としては、特に限定されないが、例えば、トマト、ピーマン、トウガラシ、ナス等のナス類、キュウリ、カボチャ、メロン、スイカ等のウリ類、セルリー、パセリー、レタス等の生菜・香辛菜類、ネギ、タマネギ、ニンニク等のネギ類、ダイズ、ラッカセイ、インゲン、エンドウ、アズキ等の豆類、イチゴ等のその他果菜類、ダイコン、カブ、ニンジン、ゴボウ等の直根類、サトイモ、キャッサバ、バレイショ、サツマイモ、ナガイモ等の芋類、アスパラガス、ホウレンソウ、ミツバ等の柔菜類、トルコギキョウ、ストック、カーネーション、キク等の花卉類、イネ、トウモロコシ等の穀物類、ベントグラス、コウライシバ等の芝類、ナタネ、ヒマワリ等の油料作物類、サトウキビ、テンサイ等の糖料作物類、ワタ、イグサ等の繊維料作物類、クローバー、ソルガム、デントコーン等の飼料作物類、リンゴ、ナシ、ブドウ、モモ等の落葉性果樹類、ウンシュウミカン、レモン、グレープフルーツ等の柑橘類、サツキ、ツツジ、スギ等の木本類が挙げられる。これらのうち、トマト、ピーマン、トウガラシ、ナス、キュウリ、カボチャ、メロン、スイカ、セルリー、パセリー、レタス、ネギ、タマネギ、アスパラガス、トルコギキョウ、ストック、イネ、ベントグラス、コウライシバ、テンサイ、イグサ等の栽培中に移植を行う植物や、キク、カーネーション、サツキ、ツツジ、ブドウ等の切り枝や挿し穂から不定根発生させることにより増殖を行う植物に対しては特に有効である。また、倒伏防止を目的とする場合のイネ科の植物としては、イネ、コムギ、オオムギ、ライムギ、トウモロコシ等が挙げられる。特にイネや麦類は分けつ期に散布することで不定根が多く発生し、根系全体の発育が促進し、栄養分の吸収効率が向上するので本発明の植物の不定根発生誘導剤及び根系発達促進剤としての効果を発揮させるのに好ましい。 The plant to which the adventitious root development inducer and root system development promoter of the plant of the present invention is applied is not particularly limited, for example, tomato, pepper, capsicum, eggplant and other eggplants, cucumber, pumpkin, melon, watermelon, etc. Cucumbers, celery, parsley, lettuce and other raw vegetables and spices, leeks, onions, garlic and other leeks, soybeans, groundnuts, green beans, peas, beans and other fruits, strawberry and other fruit vegetables, radish, turnip , Carrots, burdock roots, taro, cassava, potato, sweet potatoes, potatoes such as potatoes, asparagus, spinach, honeybees and other vegetables, eustoma, stocks, carnations, chrysanthemums, flowers, rice, Grains such as corn, turf such as bentgrass, blackgrass, oil crops such as rapeseed and sunflower, sugar crops such as sugar cane and sugar beet, textile crops such as cotton and rush, clover, sorghum, and dent corn. Examples thereof include forage crops, deciduous fruit trees such as apples, pears, grapes and peaches, citrus fruits such as unshiu mandarin oranges, lemons and grapefruits, and woods such as satsuki, azalea and cedar. Among these, during cultivation of tomato, pepper, capsicum, eggplant, cucumber, pumpkin, melon, watermelon, celery, parsley, lettuce, leeks, onion, asparagus, eustoma, stock, rice, bentgrass, koraishiba, sugar beet, rush etc. It is particularly effective for a plant to be transplanted to, or a plant to be propagated by adventitious root generation from cuttings and cuttings of chrysanthemum, carnation, satsuki, azalea, grape and the like. In addition, examples of plants of the family Gramineae for the purpose of preventing lodging include rice, wheat, barley, rye, and corn. In particular, rice and barley produce a large number of adventitious roots by being sprayed at the parting stage, which promotes the growth of the entire root system and improves the absorption efficiency of nutrients, so that the adventitious root occurrence inducer and root system development promoter of the present invention are used. It is preferable to exert the effect of.
また、本発明の効果向上を目的として、上記したように他の植物成長調整剤（植物ホルモン剤）と併用することもでき、場合によっては相乗効果を期待することもできる。例えば、高い栽植密度、高湿度、日照不足などといった極めて徒長しやすい条件下での育苗時には、地上部地下部重比の小さい良質な苗の育成を目的として、強力な茎の伸長抑制作用を持つ抗ジベレリン剤（パクロブトラゾール、ウニコナゾールＰ、アンシミドールなど）、成長抑制剤（ダミノジッドなど）、エチレン発生剤（エテホンなど）と併用してもよい。挿し穂、挿し芽、挿し木、組織培養時においては、不定根発生誘導効果の増強を目的として、オーキシン系化合物（インドール酢酸、インドール酪酸、ナフチルアセトアミド、ナフタレン酢酸など）と併用してもよい。播種前の種子処理時には、発芽誘導作用を持つジベレリン剤と併用してもよい。 Further, for the purpose of improving the effect of the present invention, it can be used in combination with other plant growth regulators (plant hormone agents) as described above, and in some cases, a synergistic effect can be expected. For example, when raising seedlings under conditions that are extremely easy to grow, such as high planting density, high humidity, lack of sunlight, etc., it has a powerful stem growth inhibitory action for the purpose of raising good quality seedlings with a small weight ratio above ground and underground. It may be used in combination with an anti-gibberellin agent (such as paclobutrazol, uniconazole P, ancimidol), a growth inhibitor (such as daminozide), and an ethylene generator (such as ethefone). At the time of cuttings, cuttings, cuttings, and tissue culture, auxin compounds (indole acetic acid, indole butyric acid, naphthyl acetamide, naphthalene acetic acid, etc.) may be used together for the purpose of enhancing adventitious root development inducing effect. At the time of seed treatment before sowing, a gibberellin agent having a germination-inducing action may be used in combination.
本発明の植物の不定根発生誘導剤及び根系発達促進剤は、各種殺虫剤、殺菌剤、微生物農薬、肥料等と混用又は併用することも可能である。特に、殺菌剤との混用において殺菌作用の他に不定根発生誘導作用も報告されているヒドロキシイソキサゾール、メタスルホカルブ、メタラキシルなどとの併用は有効である。種子に直接処理する殺虫殺菌剤や育苗期に使用する殺虫殺菌剤（チアメトキサム、フルジオキソニル、メタラキシル、クロラントラニリプロールなど）との混用は特に有効である。肥料と併用する場合、健苗育成を目的とした育苗用肥料との併用、活着促進を目的とした移植直前施用肥料との併用は特に有効である。本発明の植物成長調整剤の効力を長期間持続させ肥料成分利用率を向上させる目的とした緩効性肥料との混用も特に有効である。 The adventitious root development inducer and root system development promoter of the present invention can be mixed or used in combination with various insecticides, fungicides, microbial pesticides, fertilizers and the like. In particular, it is effective to use hydroxyisoxazole, metasulfocarb, metalaxyl and the like, which have been reported to have adventitious root development inducing action in addition to the bactericidal action when mixed with a bactericide. Mixing with an insecticidal fungicide for direct treatment of seeds or an insecticidal fungicide used during seedling raising (thiamethoxam, fludioxonil, metalaxyl, chlorantraniliprole, etc.) is particularly effective. When used in combination with a fertilizer, it is particularly effective to use it with a fertilizer for raising seedlings for the purpose of raising healthy seedlings and with a fertilizer immediately before transplantation for the purpose of promoting survival. Mixing with a slow-release fertilizer for the purpose of maintaining the potency of the plant growth regulator of the present invention for a long period of time and improving the utilization rate of fertilizer components is also particularly effective.
１．製造例
＜化合物１＞
２−アミノテレフタル酸１−メチル５.０ｇを塩化メチレン溶液５０ｍｌに溶解させ溶液とした。メチルアミン塩酸塩３．５ｇ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩４．９ｇ、トリエチルアミン１０．７ｍｌ、１−ヒドロキシベンゾトリアゾール０．３ｇを塩化メチレン溶液１００ｍｌに溶解させ溶液とした。先の溶液を後の溶液に氷冷下で添加し、室温にて一夜撹拌した。反応液を水、５％炭酸水素ナトリウム水溶液、１規定塩酸、水で順次洗浄し、無水硫酸マグネシウムで乾燥後、減圧下にて塩化メチレンを留去した。得られた結晶をアセトンにて再結晶した後、減圧乾燥した。得られた化合物０．２７ｇ、５０％エタノール５０ｍｌ、および１規定水酸化ナトリウム５ｍｌを容器に順次加え、６５℃にて１時間撹拌した。反応液に濃塩酸を加えてｐH８．０にし、酢酸エチルで抽出した後、水相に濃塩酸を加えてｐＨ２．５にし、酢酸エチルにて３回抽出した。酢酸エチル相を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去し、得られた結晶をアセトンにて再結晶後、減圧乾燥し、０．０８ｇ（収率１．６％）の化合物を得た。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式２）の構造を確認した。
1. Production Example <Compound 1>
5.0 g of 1-methyl 2-aminoterephthalate was dissolved in 50 ml of a methylene chloride solution to give a solution. Methylamine hydrochloride 3.5 g, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 4.9 g, triethylamine 10.7 ml, 1-hydroxybenzotriazole 0.3 g were dissolved in methylene chloride solution 100 ml to obtain a solution. And The above solution was added to the latter solution under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with water, 5% aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with acetone and then dried under reduced pressure. The obtained compound (0.27 g), 50% ethanol (50 ml), and 1N sodium hydroxide (5 ml) were sequentially added to the container, and the mixture was stirred at 65°C for 1 hr. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 8.0, and the mixture was extracted with ethyl acetate. Then, concentrated hydrochloric acid was added to the aqueous phase to adjust the pH to 2.5, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the obtained crystals were recrystallized from acetone, and dried under reduced pressure to give 0.08 g (yield 1.6%) of the compound. Got
The structure of (formula 2) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
＜化合物２＞
２−アミノテレフタル酸１−メチル５.０ｇを塩化メチレン溶液５０ｍｌに溶解させ溶液とした。イソプロピルアミン４．３ｍｌ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩４．９ｇ、１−ヒドロキシベンゾトリアゾール０．３ｇを塩化メチレン溶液１００ｍｌに溶解させ溶液とした。先の溶液を後の溶液に氷冷下で添加し、室温にて一夜撹拌した。反応液を水、５％炭酸水素ナトリウム水溶液、１規定塩酸、水で順次洗浄し、無水硫酸マグネシウムで乾燥後、減圧下にて塩化メチレンを留去した。得られた結晶をアセトンにて再結晶した後、減圧乾燥することによって１．３２ｇの化合物を得た（収率２２％）。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式３）の構造を確認した。
<Compound 2>
5.0 g of 1-methyl 2-aminoterephthalate was dissolved in 50 ml of a methylene chloride solution to give a solution. Isopropylamine 4.3 ml, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 4.9 g, and 1-hydroxybenzotriazole 0.3 g were dissolved in a methylene chloride solution 100 ml to give a solution. The above solution was added to the latter solution under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with water, 5% aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with acetone and then dried under reduced pressure to obtain 1.32 g of a compound (yield 22%).
The structure of (formula 3) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
＜化合物３＞
化合物２を１．０ｇ、５０％エタノール１５０ｍｌ、および１規定水酸化ナトリウム１５ｍｌを容器に順次加え、６５℃にて１時間撹拌した。反応液に濃塩酸を加えてｐH８．０にし、酢酸エチルで抽出した後、水相に濃塩酸を加えてｐＨ２．５にし、酢酸エチルにて３回抽出した。酢酸エチル相を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去し、得られた結晶をアセトンと酢酸エチルの混合液にて再結晶後、減圧乾燥し、０．１６ｇ（収率１７％）の化合物を得た。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式４）の構造を確認した。
<Compound 3>
Compound 2 (1.0 g), 50% ethanol (150 ml), and 1N sodium hydroxide (15 ml) were sequentially added to the container, and the mixture was stirred at 65°C for 1 hr. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 8.0, and the mixture was extracted with ethyl acetate. Then, concentrated hydrochloric acid was added to the aqueous phase to adjust the pH to 2.5, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the obtained crystals were recrystallized with a mixed solution of acetone and ethyl acetate, and dried under reduced pressure to give 0.16 g (yield 17 %) of the compound was obtained.
The structure of (formula 4) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
＜化合物４＞
２−アミノテレフタル酸１−メチル５.０ｇを塩化メチレン溶液５０ｍｌに溶解させ溶液とした。ｔｅｒｔ−ブチルアミン５．３ｍｌ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩４．９ｇ、トリエチルアミン３．６ｍｌ、１−ヒドロキシベンゾトリアゾール０．３ｇを塩化メチレン溶液２００ｍｌに溶解させ溶液とした。先の溶液を後の溶液に氷冷下で添加し、室温にて一夜撹拌した。反応液を水、５％炭酸水素ナトリウム水溶液、１規定塩酸、水で順次洗浄し、無水硫酸マグネシウムで乾燥後、減圧下にて塩化メチレンを留去した。得られた結晶をアセトンにて再結晶した後、減圧乾燥した。得られた化合物１．１ｇ、５０％エタノール２００ｍｌ、および１規定水酸化ナトリウム２０ｍｌを容器に順次加え、６０℃にて１時間撹拌した。反応液に濃塩酸を加えてｐH８．０にし、酢酸エチルで抽出した後、水相に濃塩酸を加えてｐＨ２．５にし、酢酸エチルにて３回抽出した。酢酸エチル相を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去し、得られた結晶をメタノールにて再結晶後、減圧乾燥し、０．０８ｇ（収率１２．５％）の化合物を得た。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式５）の構造を確認した。
<Compound 4>
5.0 g of 1-methyl 2-aminoterephthalate was dissolved in 50 ml of a methylene chloride solution to give a solution. tert-Butylamine 5.3 ml, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 4.9 g, triethylamine 3.6 ml, and 1-hydroxybenzotriazole 0.3 g were dissolved in methylene chloride solution 200 ml to prepare a solution. did. The above solution was added to the latter solution under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with water, 5% aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with acetone and then dried under reduced pressure. 1.1 g of the obtained compound, 200 ml of 50% ethanol, and 20 ml of 1N sodium hydroxide were sequentially added to the container, and the mixture was stirred at 60° C. for 1 hour. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 8.0, and the mixture was extracted with ethyl acetate. Then, concentrated hydrochloric acid was added to the aqueous phase to adjust the pH to 2.5, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from methanol and dried under reduced pressure to give 0.08 g (yield 12.5%) of the compound. Got
The structure of (formula 5) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
＜化合物５＞
２−アミノテレフタル酸１−メチル５.０ｇを塩化メチレン溶液５０ｍｌに溶解させ溶液とした。１−ブチルアミン５ｍｌ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩４．９ｇ、トリエチルアミン３．６ｍｌ、１−ヒドロキシベンゾトリアゾール０．３ｇを塩化メチレン溶液１００ｍｌに溶解させ溶液とした。先の溶液を後の溶液に氷冷下で添加し、室温にて一夜撹拌した。反応液を水、５％炭酸水素ナトリウム水溶液、１規定塩酸、水で順次洗浄し、無水硫酸マグネシウムで乾燥後、減圧下にて塩化メチレンを留去した。得られた結晶をアセトンにて再結晶した後、減圧乾燥することによって０．６９ｇの化合物を得た（収率１１％）。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式６）の構造を確認した。
<Compound 5>
5.0 g of 1-methyl 2-aminoterephthalate was dissolved in 50 ml of a methylene chloride solution to give a solution. 5 ml of 1-butylamine, 4.9 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 3.6 ml of triethylamine and 0.3 g of 1-hydroxybenzotriazole were dissolved in 100 ml of a methylene chloride solution to give a solution. The above solution was added to the latter solution under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with water, 5% aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with acetone and then dried under reduced pressure to obtain 0.69 g of a compound (yield 11%).
The structure of (formula 6) was confirmed by measuring the NMR, mass spectrum and melting point of this compound.
＜化合物６＞
化合物５を０．６ｇ、５０％エタノール５０ｍｌ、および１規定水酸化ナトリウム５ｍｌを容器に順次加え、６５℃にて１時間撹拌した。反応液に濃塩酸を加えてｐH８．０にし、酢酸エチルで抽出した後、水相に濃塩酸を加えてｐＨ２．５にし、酢酸エチルにて３回抽出した。酢酸エチル相を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去し、得られた結晶をアセトンにて再結晶後、減圧乾燥し、０．１９ｇ（収率３３％）の化合物を得た。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式７）の構造を確認した。
<Compound 6>
Compound 5 (0.6 g), 50% ethanol (50 ml), and 1N sodium hydroxide (5 ml) were sequentially added to the container, and the mixture was stirred at 65° C. for 1 hour. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 8.0, and the mixture was extracted with ethyl acetate. Then, concentrated hydrochloric acid was added to the aqueous phase to adjust the pH to 2.5, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from acetone and dried under reduced pressure to obtain 0.19 g (yield 33%) of the compound. It was
The structure of (Formula 7) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
＜化合物７＞
２−アミノテレフタル酸１−メチル５.０ｇを塩化メチレン溶液５０ｍｌに溶解させ溶液とした。シクロヘキシルアミン５ｍｌ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩４．９ｇ、トリエチルアミン３．６ｍｌ、１−ヒドロキシベンゾトリアゾール０．３ｇを塩化メチレン溶液１００ｍｌに溶解させ溶液とした。先の溶液を後の溶液に氷冷下で添加し、室温にて一夜撹拌した。反応液を水、５％炭酸水素ナトリウム水溶液、１規定塩酸、水で順次洗浄し、無水硫酸マグネシウムで乾燥後、減圧下にて塩化メチレンを留去した。得られた結晶をアセトンにて再結晶した後、減圧乾燥した。得られた化合物０．５ｇ、５０％エタノール５０ｍｌ、および１規定水酸化ナトリウム５ｍｌを容器に順次加え、６０℃にて１時間撹拌した。反応液に濃塩酸を加えてｐH８．０にし、酢酸エチルで抽出した後、水相に濃塩酸を加えてｐＨを酸性側にし、酢酸エチルにて３回抽出した。酢酸エチル相を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去し、得られた結晶をアセトンと酢酸エチルの混合液にて再結晶後、減圧乾燥し、０．１７ｇ（収率２．５％）の化合物を得た。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式８）の構造を確認した。
<Compound 7>
5.0 g of 1-methyl 2-aminoterephthalate was dissolved in 50 ml of a methylene chloride solution to give a solution. 5 ml of cyclohexylamine, 4.9 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 3.6 ml of triethylamine and 0.3 g of 1-hydroxybenzotriazole were dissolved in 100 ml of a methylene chloride solution to give a solution. The above solution was added to the latter solution under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with water, 5% aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with acetone and then dried under reduced pressure. 0.5 g of the obtained compound, 50 ml of 50% ethanol, and 5 ml of 1N sodium hydroxide were sequentially added to the container, and the mixture was stirred at 60° C. for 1 hour. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 8.0, and the mixture was extracted with ethyl acetate. Then, concentrated hydrochloric acid was added to the aqueous phase to make the pH acidic, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, the obtained crystals were recrystallized from a mixed solution of acetone and ethyl acetate, and dried under reduced pressure to give 0.17 g (yield 2 0.5%) was obtained.
The structure of (Formula 8) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
＜化合物８＞
２−アミノテレフタル酸１−メチル５.０ｇを塩化メチレン溶液５０ｍｌに溶解させ溶液とした。１−ヘキシルアミン６．６ｍｌ、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩４．９ｇ、トリエチルアミン３．６ｍｌ、１−ヒドロキシベンゾトリアゾール０．３ｇを塩化メチレン溶液１００ｍｌに溶解させ溶液とした。先の溶液を後の溶液に氷冷下で添加し、室温にて一夜撹拌した。反応液を水、５％炭酸水素ナトリウム水溶液、１規定塩酸、水で順次洗浄し、無水硫酸マグネシウムで乾燥後、減圧下にて塩化メチレンを留去した。得られた結晶をアセトンにて再結晶した後、減圧乾燥した。得られた化合物１．６ｇ、５０％エタノール１００ｍｌ、および１規定水酸化ナトリウム１０ｍｌを容器に順次加え、６０℃にて１時間撹拌した。反応液に濃塩酸を加えてｐH８．０にし、酢酸エチルで抽出した後、水相に濃塩酸を加えてｐＨ２．５にし、酢酸エチルにて３回抽出した。酢酸エチル相を無水硫酸マグネシウムで乾燥後、減圧下にて溶媒を留去し、得られた結晶をアセトンと酢酸エチルの混合液にて再結晶後、減圧乾燥し、０．４８ｇ（収率７．１％）の化合物を得た。
この化合物についてＮＭＲ、マススペクトル、融点を測定し、（式９）の構造を確認した。
<Compound 8>
5.0 g of 1-methyl 2-aminoterephthalate was dissolved in 50 ml of a methylene chloride solution to give a solution. 6.6 ml of 1-hexylamine, 4.9 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 3.6 ml of triethylamine and 0.3 g of 1-hydroxybenzotriazole were dissolved in 100 ml of methylene chloride solution to obtain a solution. And The above solution was added to the latter solution under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with water, 5% aqueous sodium hydrogen carbonate solution, 1N hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then methylene chloride was distilled off under reduced pressure. The obtained crystals were recrystallized with acetone and then dried under reduced pressure. 1.6 g of the obtained compound, 100 ml of 50% ethanol, and 10 ml of 1N sodium hydroxide were sequentially added to the container, and the mixture was stirred at 60° C. for 1 hour. Concentrated hydrochloric acid was added to the reaction solution to adjust the pH to 8.0, and the mixture was extracted with ethyl acetate. Then, concentrated hydrochloric acid was added to the aqueous phase to pH 2.5, and the mixture was extracted 3 times with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the obtained crystals were recrystallized from a mixed solution of acetone and ethyl acetate and dried under reduced pressure to give 0.48 g (yield 7 0.1%) was obtained.
The structure of (formula 9) was confirmed by measuring NMR, mass spectrum and melting point of this compound.
化合物１〜８のＮＭＲ測定結果並びに融点の測定結果を下記の表１に示す。 The NMR measurement results and melting point measurement results of Compounds 1 to 8 are shown in Table 1 below.
２．試験例
＜アズキ切り口浸漬処理による不定根の発生誘導作用の確認試験＞
上記の化合物１〜８について蒸留水で希釈し、濃度が０．１ｍＭ、０．３ｍＭ、１ｍＭの水溶液を調製し、希塩酸と水酸化ナトリウム水溶液を用いてｐＨ７とし、アズキ不定根発生促進アッセイ(Itagaki et al. 2003. Biological activities and structure-activity relationship of substitution compounds of N-[2-(3-indolyl)ethyl] succinamic acid and N-[2-(1-naphthyl)ethyl] succinamic acid，derived from a new category of root-promoting substance， N-(phenethyl)succinamic acid analogs. Plant Soil 255: 67-75.)を行った。
また、不定根の発生剤として公知のオーキシンであるインドール酢酸（ＩＡＡ）１０μＭと併用することによる効果を確認する試験を行った。
アズキ切片は基部を４８時間、０．１ｍＭ、０．３ｍＭ及び１ｍＭの各被検液に浸漬し、７日後に発生した不定根数を数えた。反復数は５本とした。またＩＡＡとの併用試験の場合、被検液の濃度は、０．１ｍＭ、０．３ｍＭの濃度とした。なお、各化合物の活性を測定する際に、対照として蒸留水（ＤＷ）で処理したものを培養し、同様に不定根数を測定した。このため、対照区は複数回測定した総平均値を示した。
試験結果を下記表２に示す。
2. Test example <Confirmation test of adventitious root generation inducing action by azuki bean cut dipping treatment>
The above compounds 1 to 8 were diluted with distilled water to prepare an aqueous solution having a concentration of 0.1 mM, 0.3 mM and 1 mM, adjusted to pH 7 with dilute hydrochloric acid and an aqueous sodium hydroxide solution, and an adzuki bean adventitious root development assay (Itagaki et al. 2003. Biological activities and structure-activity relationship of substitution compounds of N-[2-(3-indolyl)ethyl] succinamic acid and N-[2-(1-naphthyl)ethyl] succinamic acid, derived from a new category. of root-promoting substance, N-(phenethyl)succinamic acid analogs. Plant Soil 255: 67-75.).
Further, a test was conducted to confirm the effect of the combined use with 10 μM of indoleacetic acid (IAA), which is a known auxin as an adventitious root generator.
The base of the adzuki bean slice was immersed for 48 hours in each test solution of 0.1 mM, 0.3 mM and 1 mM, and after 7 days, the number of adventitious roots was counted. The number of repetitions was 5. In the case of the combined use test with IAA, the concentrations of the test liquid were 0.1 mM and 0.3 mM. When measuring the activity of each compound, the one treated with distilled water (DW) was cultured as a control, and the number of adventitious roots was similarly measured. Therefore, the control group showed the total average value measured multiple times.
The test results are shown in Table 2 below.
表１に示すとおり化合物１〜６を含有する溶液は、対照区（蒸留水）の不定根発生数と比較すると高い不定根発生誘導作用と不定根発生促進作用が認められた。この作用は濃度依存的であることが判明した。また、インドール酢酸（ＩＡＡ）と併用すると、その不定根発生作用はより増強された。
また、化合物３および６のＲ２（−ＯＨ）をメトキシ基に置換した化合物である化合物２および５は、同等の不定根発生作用をもつことが確認された。
As shown in Table 1, the solutions containing Compounds 1 to 6 were found to have a higher adventitious root generation-inducing action and adventitious root generation-promoting action than the number of adventitious root generation in the control group (distilled water). This effect was found to be concentration dependent. When used in combination with indole acetic acid (IAA), its adventitious root-generating action was further enhanced.
It was also confirmed that compounds 2 and 5, which are compounds 3 and 6 in which R2(-OH) was substituted with a methoxy group, had an equivalent adventitious root-generating action.
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