JPWO2016035685A1 - Adventitious root development inducer and root system development promoter - Google Patents
Adventitious root development inducer and root system development promoter Download PDFInfo
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- JPWO2016035685A1 JPWO2016035685A1 JP2016546604A JP2016546604A JPWO2016035685A1 JP WO2016035685 A1 JPWO2016035685 A1 JP WO2016035685A1 JP 2016546604 A JP2016546604 A JP 2016546604A JP 2016546604 A JP2016546604 A JP 2016546604A JP WO2016035685 A1 JPWO2016035685 A1 JP WO2016035685A1
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- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05F—ORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C, e.g. FERTILISERS FROM WASTE OR REFUSE
- C05F11/00—Other organic fertilisers
- C05F11/10—Fertilisers containing plant vitamins or hormones
Abstract
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。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【化1】(ただし、一般(式1)のR1〜R6は次のいずれかの構造である。R1= ヒドロキシ基、アルコキシ基、又はアミノ基R2= 水素原子、アルキル基、フェニル基又はアシル基R3= 水素原子、水酸基、ハロゲン原子、アルキル基又はアルコキシ基R4= 水素原子、ハロゲン原子、アミノ基、カルボキシル基R5= 水素原子、アルキル基、ハロゲン原子又はニトロ基R6= 水素原子)。To provide a plant adventitious root development inducer and a root system development promoter. 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: embedded image (where R1 to R6 in the general formula (formula 1) are any of the following: R1 = hydroxy group, alkoxy group, or amino group R2 = hydrogen atom, alkyl group, phenyl group or acyl group R3 = hydrogen atom, hydroxyl group, halogen atom, alkyl group or alkoxy group R4 = hydrogen atom, Halogen atom, amino group, carboxyl group R5 = hydrogen atom, alkyl group, halogen atom or nitro group R6 = hydrogen atom).
Description
本発明は、植物の不定根発生誘導剤及び根系発達促進剤に関する。 The present invention relates to a plant adventitious root development inducer and a root system development promoter.
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. Currently, various types of plant growth regulators aimed at controlling plant growth have been put into practical use, and plant growth regulators contribute to the improvement of crop yield and product quality. Among them, roots play a very important role in plant settlement, water absorption, nutrient absorption, and prevention of lodging, so it is important to promote their development.
Plant roots are composed of main roots, lateral roots and adventitious roots, and these are collectively called the root system. The main root has already developed at the seed stage and grows simultaneously with germination. Lateral roots differentiate and develop from the main roots. Adventitious roots differentiate and develop from tissues other than roots such as stems and leaves. For this reason, roots generated from cultured cells of plants and roots generated from above-ground tissue sections such as cuttings and cuttings are classified as adventitious roots, which induces the occurrence of adventitious roots to promote so-called vegetative propagation efficiently. Has become an important industrial technology. In addition, monocotyledonous plants such as gramineous crops stop the growth of young roots shortly after germination, and most roots except seed roots are adventitious roots generated from stems and are also called crown roots. Inducing the occurrence of these adventitious roots is important for ensuring stable growth of gramineous plants. Adventitious root generation is particularly important for the growth and prevention of lodging of the main 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、現在発根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。
WO2011/136285号公報(特許文献1)にはクロロフェニル基やジク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 generation and promoting root system development is desired. However, plant growth regulators that induce the occurrence of adventitious roots have a small number, are not sufficiently effective, and often have an undesirable action. For example, auxin compounds that are currently widely used as rooting agents are toxic to plants depending on the type and condition of the plant and the concentration applied, and have undesirable effects such as chlorosis and death of stems and leaves. Sometimes.
WO 2011/136285 (Patent Document 1) describes that a compound having a chlorophenyl group, a dichlorophenyl group, or the like generates eucalyptus adventitious roots. JP-A-5-260869 (Patent Document 2) describes that adventitious roots can be induced in the stem of sweet potato when auxin and α-naphthaleneacetic acid are used in combination. Furthermore, JP-A-5-49484 (Patent Document 3) describes a technique for inducing the occurrence of adventitious roots by culturing callus of lemon balm in a medium supplemented with 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4)。
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、むしろ植物生長抑制物質として認識されていた(非特許文献5)。Among plant hormones, indoleacetic acid is known to induce the development of adventitious 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, and as a result, lateral root development is induced (Non-patent Document 3). There has been no report on adventitious root development inducing activity, and conversely, when anthranilic acid itself was applied to plants, adventitious root development was not induced (Non-patent Document 4).
That is, as described above, since anthranilic acid was considered as a precursor of indoleacetic acid, it was not considered to have an adventitious root generation promoting action unless converted to tryptophan or indoleacetic acid. Furthermore, since the derivative was not converted to indoleacetic acid, it was theoretically not considered to have an indeterminate root development inducing action or root system development inducing action. From this, the anthranilic acid derivative was supposed to inhibit tryptophan synthase activity as a result, and was rather recognized as a plant growth inhibitor (Non-patent Document 5).
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 generation 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見出すことができ、本発明を完成するに至った。 As a result of diligent research to solve the above problems, the present inventors have found that anthranilic acid, which is conventionally considered to have no adventitious root development-inducing action, induces the occurrence of adventitious roots and further promotes the development of root systems. I found it. This action can also be found in derivatives of anthranilic acid, and the present invention has been completed.
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および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, this invention consists of the following structures.
1. Plant adventitious root development inducer and root system development promoter comprising the compound represented by the following (formula 1) or a salt and ester thereof
(ただし、(式1)のR1〜R6は次のいずれかの構造である。
R1= ヒドロキシ基、アルコキシ基、又はアミノ基
R2= 水素原子、アルキル基、フェニル基又はアシル基
R3= 水素原子、水酸基、ハロゲン原子、アルキル基又はアルコキシ基
R4= 水素原子、ハロゲン原子、アミノ基、カルボキシル基
R5= 水素原子、アルキル基、ハロゲン原子又はニトロ基
R6= 水素原子)。
2.R1のアルコキシ基がメトキシ基、R2のアルキル基がメチル基又はエチル基、アルコキシ基がメトキシ基、R3のハロゲン原子が塩素または臭素、R4のハロゲン原子が塩素、R5のアルキル基がメチル基、ハロゲン原子が塩素、臭素、ヨウ素のいずれかである、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
3.R1がヒドロキシ基、アルコキシ基、又はアミノ基であり、R2、R4、R6が水素原子であり、R3が水素原子、メチル基、塩素原子、臭素原子のいずれか、R5が塩素原子又は臭素原子である、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
4.R1がヒドロキシ基、R2〜R6が水素原子である、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
5.R1がメトキシ基又はアミノ基であり、R2〜R6が水素原子である、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
6.R1がヒドロキシ基、R2、R4〜R6が水素原子であり、R3が水酸基、メチル基、メトキシ基、塩素又は臭素原子のいずれかである、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
7.R1がヒドロキシ基、R2〜R3、R5、R6が水素原子、R4が塩素原子、アミノ基、カルボキシル基のいずれかである、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
8.R1がヒドロキシ基、R2〜R4、R6が水素原子であり、R5がメチル基、塩素原子、臭素原子、ヨウ素原子、ニトロ基のいずれかである、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
9.R1がヒドロキシ基、R2、R4、R6が水素原子であり、R3がメチル基、塩素原子、臭素原子のいずれか、R5が塩素原子又は臭素原子である、1記載の植物の不定根発生誘導剤及び根系発達促進剤。
10.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1〜9記載の植物の不定根発生誘導剤及び根系発達促進剤。
11.1〜10記載の植物の不定根発生誘導剤及び根系発達促進剤を含有する肥料。
12.1〜10記載の植物の不定根発生誘導剤及び根系発達促進剤を含有する農薬。
13.アントラニル酸、アントラニル酸メチル、アントラニルアミド、N−メチルアントラニル酸、N−エチルアントラニル酸、N−フェニルアントラニル酸、N−アセチルアントラニル酸、3−ヒドロキシアントラニル酸、3−メチルアントラニル酸、3−メトキシアントラニル酸、3−クロロアントラニル酸、4−アミノアントラニル酸、2−アミノテレフタル酸、4−クロロアントラニル酸、5−クロロアントラニル酸、5−ブロモアントラニル酸、5−ヨードアントラニル酸、5−ニトロアントラニル酸、3,5−ジメチルアントラニル酸、5−クロロ−3−メチルアントラニル酸、3,5−ジクロロアントラニル酸、3,5−ジブロモアントラニル酸のいずれか1以上を含有する植物の不定根発生誘導剤及び根系発達促進剤。
14.13に記載の植物の不定根発生誘導剤及び根系発達促進剤を含有する肥料。
15.13に記載の植物の不定根発生誘導剤及び根系発達促進剤を含有する農薬。
(However, R < 1 > -R < 6 > of (Formula 1) is one of the following structures.
R 1 = hydroxy group, alkoxy group, or amino group R 2 = hydrogen atom, alkyl group, phenyl group or acyl group R 3 = hydrogen atom, hydroxyl group, halogen atom, alkyl group or alkoxy group R 4 = hydrogen atom, halogen atom Amino group, carboxyl group R 5 = hydrogen atom, alkyl group, halogen atom or nitro group R 6 = hydrogen atom).
2. The alkoxy group of R 1 is a methoxy group, the alkyl group of R 2 is a methyl group or an ethyl group, the alkoxy group is a methoxy group, the halogen atom of R 3 is chlorine or bromine, the halogen atom of R 4 is chlorine, and the alkyl group of R 5 2. The plant adventitious root generation inducer and root system development promoter according to 1, wherein is a methyl group and a halogen atom is chlorine, bromine, or iodine.
3. R 1 is a hydroxy group, an alkoxy group, or an amino group, R 2 , R 4 , and R 6 are hydrogen atoms, R 3 is any one of a hydrogen atom, a methyl group, a chlorine atom, and a bromine atom, and R 5 is 2. The plant adventitious root generation inducer and root system development promoter according to 1, which is a chlorine atom or a bromine atom.
4). The plant adventitious root development inducer and root system development promoter according to 1, wherein R 1 is a hydroxy group, and R 2 to R 6 are hydrogen atoms.
5. The plant adventitious root development inducer and root system development promoter according to 1, wherein R 1 is a methoxy group or an amino group, and R 2 to R 6 are hydrogen atoms.
6). The plant adventitious root generation inducer according to 1, wherein R 1 is a hydroxy group, R 2 , R 4 to R 6 are hydrogen atoms, and R 3 is any one of a hydroxyl group, a methyl group, a methoxy group, chlorine, or a bromine atom. And root system development promoter.
7). The plant adventitious root formation inducer and root system development according to 1, wherein R 1 is a hydroxy group, R 2 to R 3 , R 5 , R 6 are hydrogen atoms, R 4 is a chlorine atom, an amino group, or a carboxyl group. Accelerator.
8). The adventitious root generation of the plant according to 1, wherein R 1 is a hydroxy group, R 2 to R 4 , R 6 are hydrogen atoms, and R 5 is any one of a methyl group, a chlorine atom, a bromine atom, an iodine atom, and a nitro group Inducing agent and root system development promoter.
9. The plant according to 1, wherein R 1 is a hydroxy group, R 2 , R 4 , and R 6 are hydrogen atoms, R 3 is any one of a methyl group, a chlorine atom, and a bromine atom, and R 5 is a chlorine atom or a bromine atom. Adventitious root development inducer and root system development promoter.
10. The plant adventitious root generation inducing agent and root system development promoting agent according to 1 to 9, which are directly sprayed on a plant body to generate adventitious roots.
11. A fertilizer containing the plant adventitious root generation inducer and root system development promoter according to 11.1 to 10.
Agrochemicals containing the plant adventitious root generation inducer and root system development promoter of 12.1-10 description.
13. Anthranilic acid, methyl anthranilate, anthranilamide, N-methylanthranilic acid, N-ethylanthranilic acid, N-phenylanthranilic acid, N-acetylanthranilic acid, 3-hydroxyanthranilic acid, 3-methylanthranilic acid, 3-methoxyanthranilic acid Acid, 3-chloroanthranilic acid, 4-aminoanthranilic acid, 2-aminoterephthalic acid, 4-chloroanthranilic acid, 5-chloroanthranilic acid, 5-bromoanthranilic acid, 5-iodoanthranilic acid, 5-nitroanthranilic acid, Plant adventitious root development inducer and root system development containing any one or more of 3,5-dimethylanthranilic acid, 5-chloro-3-methylanthranilic acid, 3,5-dichloroanthranilic acid and 3,5-dibromoanthranilic acid Accelerator.
14. A fertilizer containing the plant adventitious root development inducer and root system development promoter according to 14.13.
15. A pesticide containing the plant adventitious root development inducer and root system development promoter according to 15.13.
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・移植時の発根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。 According to the present invention, a novel plant adventitious root development inducer and root system development promoter are provided. The plant adventitious root generation inducing agent and root system development promoting agent of the present invention have high adventitious root inducing activity and extremely weak side effects such as stem and leaf chlorosis. The plant adventitious root generation inducing agent and root system development promoting agent of the present invention are useful as rooting promoting agents at the time of cutting, seedling raising period and transplantation. Moreover, since the crown root of the grass family plant is adventitious, it acts as a crown root development promoter of the grass family and is useful for preventing lodging. Moreover, in order to promote root system development, the absorption efficiency of a fertilizer component improves and it promotes the growth of a plant. Furthermore, when the agent of the present invention is used for raising seedlings, it is possible to produce healthy seedlings with better rooting and good growth.
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 plant adventitious root generation inducer and root system development promoter of the present invention comprises a compound represented by the formula 1, a salt thereof or an ester thereof as an active ingredient.
ただし、(式1)のR1〜R6は次のいずれかの構造である。
R1= ヒドロキシ基、アルコキシ基又はアミノ基
R2= 水素原子、アルキル基、フェニル基又はアシル基
R3= 水素原子、水酸基、ハロゲン原子、アルキル基又はアルコキシ基
R4= 水素原子、ハロゲン原子、アミノ基、カルボキシル基
R5= 水素原子、アルキル基、ハロゲン原子又はニトロ基
R6= 水素原子
However, R < 1 > -R < 6 > of (Formula 1) is one of the following structures.
R 1 = hydroxy group, alkoxy group or amino group R 2 = hydrogen atom, alkyl group, phenyl group or acyl group R 3 = hydrogen atom, hydroxyl group, halogen atom, alkyl group or alkoxy group R 4 = hydrogen atom, halogen atom, Amino group, carboxyl group R 5 = hydrogen atom, alkyl group, halogen atom or nitro group R 6 = hydrogen atom
上記化合物は、アントラニル酸として公知の化合物あるいはその誘導体、又はその塩である。本発明の植物の不定根発生誘導剤及び根系発達促進剤の有効成分は、上記 (式1)で表される化合物である。
上記(式1)の置換基であるR1としては、ヒドロキシ基、アミノ基又は低級アルコキシ基であり、低級アルコキシ基としては、メトキシ基、エトキシ基、n−プロポキシ基、n−ペントキシ基、n−ヘクトキシ基、i−プロポキシ基、i−ブトキシ基、i−ペントキシ基及びi−ヘクトキシ基などの炭素数1〜6のアルコキシ基が挙げられる。特にメトキシ基が好ましい。The compound is a compound known as anthranilic acid, a derivative thereof, or a salt thereof. The active ingredient of the plant adventitious root generation inducer and root system development promoter of the present invention is a compound represented by the above (Formula 1).
R 1 as a substituent of the above (formula 1) is a hydroxy group, an amino group or a lower alkoxy group, and examples of the lower alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an n-pentoxy group, n Examples thereof include alkoxy groups having 1 to 6 carbon atoms such as -heptoxy group, i-propoxy group, i-butoxy group, i-pentoxy group and i-heptoxy group. A methoxy group is particularly preferable.
R2は、水素原子、置換基を有してもよいフェニル基、低級アルキル基、アセチル基である。低級アルキル基としては、メチル基、エチル基、n−プロピル基、n−ペンチル基、n−ヘキシル基、i−プロピル基、i−ブチル基、i−ペンチル基及びi−ヘキシル基などの炭素数1〜6のアルキル基が挙げられる。特にメチル基およびエチル基が好ましい。R 2 is a hydrogen atom, an optionally substituted phenyl group, a lower alkyl group, or an acetyl group. As the lower alkyl group, carbon number such as methyl group, ethyl group, n-propyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, i-pentyl group and i-hexyl group 1-6 alkyl groups are mentioned. A methyl group and an ethyl group are particularly preferable.
R3は水素原子、ハロゲン原子、低級アルキル基、低級アルコキシル基、水酸基である。
低級アルキル基としては、メチル基、エチル基、n−プロピル基、n−ペンチル基、n−ヘキシル基、i−プロピル基、i−ブチル基、i−ペンチル基及びi−ヘキシル基などの炭素数1〜6のアルキル基が挙げられる。特にメチル基が好ましい。また、低級アルコキシ基としては、メトキシ基、エトキシ基、n−プロポキシ基、n−ブトキシ基、n−ペンチルオキシ基、n−ヘキシルオキシ基、i−プロポキシ基、i−ブトキシ基、i−ペンチルオキシ基、i−ヘキシルオキシ基などの炭素数1〜6のアルコキシ基が好ましい。特にメトキシ基が好ましい。
ハロゲン原子としては塩素原子、臭素原子及びヨウ素原子が好ましい。
R4は、水素原子、ハロゲン原子、アミノ基、カルボキシル基である。ハロゲン原子としては塩素原子、臭素原子及びヨウ素原子が好ましい。特に塩素原子が好ましい。
R5は水素原子、アルキル基、ハロゲン原子、ニトロ基である。アルキル基は低級アルキル基である。低級アルキル基としては、メチル基、エチル基、n−プロピル基、n−ペンチル基、n−ヘキシル基、i−プロピル基、i−ブチル基、i−ペンチル基及びi−ヘキシル基などの炭素数1〜6のアルキル基が挙げられる。特にメチル基が好ましい。
ハロゲン原子としては塩素原子、臭素原子及びヨウ素原子が好ましい。
R3、R4、R5の置換基は相互に交換可能である。
またR6は水素原子である。R6を置換すると植物の不定根発生誘導剤及び根系発達促進剤としての活性を失ってしまう。R 3 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group, or a hydroxyl group.
As the lower alkyl group, carbon number such as methyl group, ethyl group, n-propyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, i-pentyl group and i-hexyl group 1-6 alkyl groups are mentioned. A methyl group is particularly preferable. The lower alkoxy group includes methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, i-pentyloxy. And an alkoxy group having 1 to 6 carbon atoms such as an i-hexyloxy group. A methoxy group is particularly preferable.
As a halogen atom, a chlorine atom, a bromine atom, and an iodine atom are preferable.
R 4 is a hydrogen atom, a halogen atom, an amino group, or a carboxyl group. As a halogen atom, a chlorine atom, a bromine atom, and an iodine atom are preferable. A chlorine atom is particularly preferable.
R 5 is a hydrogen atom, an alkyl group, a halogen atom, or a nitro group. An alkyl group is a lower alkyl group. As the lower alkyl group, carbon number such as methyl group, ethyl group, n-propyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, i-pentyl group and i-hexyl group 1-6 alkyl groups are mentioned. A methyl group is particularly preferable.
As a halogen atom, a chlorine atom, a bromine atom, and an iodine atom are preferable.
The substituents of R 3 , R 4 and R 5 are interchangeable.
R 6 is a hydrogen atom. When R 6 is substituted, the plant's activity as an adventitious root development inducer and root system development promoter is lost.
(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との塩が挙げられる。
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 salts with organic base salts such as pyridine salt, picoline salt, ethanolamine salt, triethanolamine salt, dicyclohexylamine salt, or organic amine salt of N, N′-dibenzylethylenediamine salt.
In addition, examples include inorganic acid salts such as hydrochloride, sulfate, and nitrate, and salts such as organic acid salts such as formate, acetate, propionate, butyrate, and lactate.
(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 esters.
(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。合成はアントラニル酸を出発物質として、R1〜R6の置換基を公知の置換反応により合成することができる。
さらにアントラニル酸は、公知の方法(米国特許第4276433号)により合成することができる。また市販品を用いてもよい。The following substance can be illustrated as an example of a useful compound by the compound shown by (Formula 1). They can be synthesized as needed. The synthesis can be performed by a known substitution reaction using R 1 to R 6 substituents starting from anthranilic acid.
Furthermore, anthranilic acid can be synthesized by a known method (US Pat. No. 4,276,433). Commercial products may also be used.
置換反応の一例としてR1をアルコキシ基に置換する置換反応を例示する。
アントラニル酸誘導体を原料として、例えば硫酸、p−トルエンスルホン酸などの酸触媒の存在下にて、メタノール、エタノール、プロパノールなどのアルコール中、加熱還流することによって、R1がアルコキシ基に置換された化合物を得る。この時、アントラニル酸誘導体は1〜20質量%、特に5〜10質量%であることが好ましい。
また、アントラニル酸誘導体を原料として、例えばトリメチルシリルジアゾメタンなどのメチルエステル化剤の存在下にて、メタノール中にて反応することによって、R1がメチル基に置換された化合物を得る。
N−アルキルアントラニル酸誘導体を合成する場合は、トルエン、テトラヒドロフランといった不活性有機溶媒中、2位に塩素または臭素置換した任意の安息香酸誘導体と任意のアルキルアミンを加え、パラジウム触媒、ニッケル触媒、銅触媒などを加え、加熱することにより合成することもできる。この時、安息香酸誘導体およびアルキルアミンは1〜20質量%、特に5〜10質量%であることが好ましい。また、触媒は1〜5モル%であることが望ましい。
反応後、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。
なお、上記以外の置換反応については、公知の化学反応で容易に行うことができる。
これらの化合物は水可溶性であることが望ましいが、水不溶性化合物の場合、水に分散する形態にして使用することができる。As an example of the substitution reaction, a substitution reaction in which R 1 is substituted with an alkoxy group is illustrated.
By using an anthranilic acid derivative as a raw material and heating to reflux in an alcohol such as methanol, ethanol or propanol in the presence of an acid catalyst such as sulfuric acid or p-toluenesulfonic acid, R 1 was substituted with an alkoxy group. A compound is obtained. At this time, it is preferable that an anthranilic acid derivative is 1-20 mass%, especially 5-10 mass%.
Further, by using an anthranilic acid derivative as a raw material and reacting in methanol in the presence of a methyl esterifying agent such as trimethylsilyldiazomethane, a compound in which R 1 is substituted with a methyl group is obtained.
When synthesizing an N-alkylanthranilic acid derivative, an arbitrary benzoic acid derivative substituted with chlorine or bromine at the 2-position and an arbitrary alkylamine are added in an inert organic solvent such as toluene or tetrahydrofuran, and a palladium catalyst, nickel catalyst, copper It can also be synthesized by adding a catalyst and heating. At this time, it is preferable that a benzoic acid derivative and an alkylamine are 1-20 mass%, especially 5-10 mass%. Further, the catalyst is desirably 1 to 5 mol%.
To collect the product from the reaction solution after the reaction, the reaction solvent is distilled off, a product-soluble organic solvent that is not mixed with water and water are added, the pH of the aqueous phase is adjusted appropriately, solvent extraction is performed, and the organic solvent is extracted. After recovering the solvent layer, it is dried and the organic solvent is distilled off, and then recrystallized from a single or mixed solvent as necessary. Moreover, what is necessary is just to isolate by separation means, such as a high performance liquid chromatography (HPLC), as needed.
In addition, about substitution reaction other than the above, it can carry out easily by a well-known chemical reaction.
These compounds are desirably water-soluble, but water-insoluble compounds can be used in the form of being dispersed in water.
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ない。
化合物1
アントラニル酸(Anthranilic acid)Typical compound names and chemical formulas useful as plant adventitious root development inducers and root system development promoters in the present invention are shown below. Of course, the present invention is not limited to these compounds.
Compound 1
Anthranilic acid
化合物2
アントラニル酸メチル(Methyl Anthranilate)Compound 2
Methyl Anthranilate
化合物3
アントラニルアミド(Anthranil amide)Compound 3
Anthranil amide
化合物4
N−メチルアントラニル酸(N-Methylanthranilic acid)Compound 4
N-Methylanthranilic acid
化合物5
N−エチルアントラニル酸(N-Ethylanthranilic acid)Compound 5
N-Ethylanthranilic acid
化合物6
N−フェニルアントラニル酸(N-Phenylanthranilic acid)Compound 6
N-Phenylanthranilic acid
化合物7
N−アセチルアントラニル酸(N-Acetylanthranilic acid)Compound 7
N-Acetylanthranilic acid
化合物8
3−ヒドロキシアントラニル酸(3-Hydroxyanthranilic acid)Compound 8
3-Hydroxyanthranilic acid
化合物9
3−メチルアントラニル酸(3-Methylanthranilic acid)Compound 9
3-Methylanthranilic acid
化合物10
3−メトキシアントラニル酸(3-Methoxyanthranilic acid)Compound 10
3-Methoxyanthranilic acid
化合物11
3−クロロアントラニル酸(3-Chloroanthranilic acid)Compound 11
3-Chloroanthranilic acid
化合物12
4−アミノアントラニル酸(4-Aminoanthranilic acid)Compound 12
4-Aminoanthranilic acid
化合物13
2−アミノテレフタル酸(2-Aminoterephthalic acid)Compound 13
2-Aminoterephthalic acid
化合物14
4−クロロアントラニル酸(4-Chloroanthranilic acid)Compound 14
4-Chloroanthranilic acid
化合物15
5−クロロアントラニル酸(5-Chloroanthranilic acid)Compound 15
5-Chloroanthranilic acid
化合物16
5−ブロモアントラニル酸(5-Bromoanthranilic acid)Compound 16
5-Bromoanthranilic acid
化合物17
5−ヨードアントラニル酸(5-Iodoanthranilic acid)Compound 17
5-Iodoanthranilic acid
化合物18
5−ニトロアントラニル酸(5-Nitroanthranilic acid)Compound 18
5-Nitroanthranilic acid
化合物19
3,5−ジメチルアントラニル酸(3,5-Dimethylanthranilic acid)Compound 19
3,5-Dimethylanthranilic acid
化合物20
5−クロロ−3−メチルアントラニル酸(5-Chloro-3-methylanthranilic acid)Compound 20
5-Chloro-3-methylanthranilic acid
化合物21
3,5−ジクロロアントラニル酸(3,5-Dichloroanthranilic acid)Compound 21
3,5-Dichloroanthranilic acid
化合物22
3,5−ジブロモアントラニル酸(3,5-Dibromoanthranilic acid)Compound 22
3,5-Dibromoanthranilic acid
また、アントラニル酸を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用いる場合は、アントラニル酸がトリプトファンの前駆体であるため、トリプトファン生合成能をもつ微生物を適宜突然変異育種や遺伝子組換えし、アントラニル酸を蓄積できるようにすれば発酵法によっても製造することができる、さらに醗酵培養液を直接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用いることができる。 Further, when anthranilic acid is used as an adventitious root development inducer and root system development promoter of the plant of the present invention, since anthranilic acid is a precursor of tryptophan, a microorganism having the ability to biosynthesize tryptophan is appropriately selected for mutation breeding and gene assembly. In other words, if anthranilic acid can be accumulated, it can also be produced by a fermentation method, and the fermentation broth can be directly used as a plant adventitious root development inducer and root system development promoter of the present invention.
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。
さらに驚くべきことに、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このような作用を有しないアミノ酸の一種であるトリプトファンと併用することで、そ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作用を増強することが可能である。The plant adventitious root development inducer and root system development promoter of the present invention can be used in combination of two or more compounds having a plurality of active actions. It can also be used in combination with plant hormones such as auxin.
Surprisingly, the plant adventitious root development inducer and root system development promoter of the present invention are used in combination with tryptophan, which is a kind of amino acid having no such action, so that the plant adventitious root development inducer and root system development can be obtained. It is possible to enhance the action as an accelerator.
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、上記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。 The plant adventitious root generation inducer and root system development promoter of the present invention can be used as an adventitious root generation inducer and root system development promoter of the above-mentioned compounds as they are, but wettable powders, emulsions, granules, You may formulate using the support | carrier used with a normal plant growth regulator, such as a powder agent and surfactant. For example, as a solid carrier, mineral powder (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate, phosphorus lime, etc.), vegetable powder (soy flour, wheat flour, wood flour, tobacco) Powder, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin, polyvinyl alcohol resin, polyvinyl acetate resin, polyvinyl chloride, ketone resin, etc.), 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, etc., any of nonionic, anionic, cationic and zwitterionic can be used. Examples of surfactants that can be used in the present invention include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl 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 salt, alkyl aryl sulfonate salt, alkyl phosphate salt, 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 and the like 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 plant adventitious root generation inducing agent and root system development promoter of the present invention are not limited in the shape of the preparation, and are formed into various preparation forms such as powders, granules, granules, wettable powders, flowables, emulsions and pastes. can do. Other components can be produced by mixing, stirring, spray drying and the like according to a conventional method.
When applied to a plant, it can be used as a soil treatment agent, a foliage treatment agent, a seed treatment agent before sowing, a treatment agent for a plant before transplantation, a treatment agent for a plant at the time of transplantation, or the like. In hydroponics, it may be used by mixing with a hydroponic solution, and in tissue culture, it may be suspended or dissolved in a medium.
If the plant adventitious root generation inducer and root system development promoter of the present invention are applied to the target plant, the root mass and root density increase through the increase in the number of roots such as the number of lateral roots and the number of adventitious roots. Improvement of survival rate, growth of healthy seedlings, promotion of growth, improvement of water absorption, improvement of fertilizer absorption, improvement of fertilizer component utilization rate, green retention, improvement of photosynthetic capacity, improvement of water stress resistance, prevention of lodging, increase in yield, etc. The effect is obtained. Moreover, since the heat rise of the grass family plant is improved, 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 plant adventitious root generation inducer and root system development accelerator 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. In particular, when used for seedlings in the seedling raising period, it is desirable to spray 50 to 200 mL of the diluted solution having the above concentration per 1 L of the culture soil. In this case, a spreading agent may be used, and the type and amount of the spreading agent to be used are not particularly limited. In addition, the effect is demonstrated even if foliar spraying.
The amount used when directly applied to the soil, including the case of mixing with fertilizer, is preferably 100 to 10,000 g, particularly 500 to 5000 g per hectare. In particular, when used for seedlings at the seedling raising stage, it is desirable to use 0.001 to 10 g per liter of culture soil. In this case, it may be preliminarily mixed in 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) Methylene, etc.), ethers (diethyl ether, etc.), esters (ethyl acetate, etc.) and other liquid carriers diluted to 0.01-100,000 ppm and sprayed on the dried seeds or immersed in the diluent. And can be absorbed by the seeds. Although it does not restrict | limit especially as immersion time, 1 second-120 minutes are preferable. In addition, the liquid carrier may be evaporated from the treated seeds by air drying, reduced pressure drying, heat drying, vacuum drying, or the like. What was formulated using a solid carrier of mineral powder such as clay can be used by adhering to the seed surface. It can also be mixed with a commonly used seed coating agent or seed coating film to coat the seed.
When used in tissue culture or cell culture, the concentration in the medium of a commonly used medium for plant tissue culture (MS medium, white medium, Gamborg B5 medium, etc.) is preferably 0.01 to 10,000 ppm, particularly preferably. It can be dissolved or suspended in the range of 0.1 to 1000 ppm. In this case, as usual, saccharides as a carbon source (sucrose, glucose, etc.), cytokinins (benzyladenine, kinetin, etc.), auxins (indole acetic acid, naphthalene acetic acid, etc.), gibberellins (GA3) as various plant hormones , GA4, etc.), abscisic acid and the like can be added as appropriate.
When it is directly absorbed by a plant before transplantation, the root or whole of the plant can be used by immersing it in a solution diluted or suspended at a use concentration of 0.1 to 1000 ppm. Moreover, if it is a cutting head, cutting bud, cutting, etc., a base part 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. What was formulated using a solid carrier of mineral powder may be attached to the root, or in the case of cuttings, cuttings, cuttings, cuttings, etc.
As the time of administration of the adventitious root development inducer and root system development promoter of the plant of the present invention, it can be used at any time during the growth period, but in particular when applied as an adventitious root development inducer, root system development promoter, It is particularly effective before sowing, during sowing, during seedling growth, before and after work involving cultivated rooting such as transplantation, or when root development is inhibited or root damage is caused by 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発根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 generation inducer and root system development accelerator of the plant of the present invention are applied is not particularly limited, but examples include eggplants such as tomatoes, peppers, peppers, eggplants, cucumbers, pumpkins, melons, watermelons, etc. Fresh vegetables such as cucumbers, celery, parsley, lettuce, green onions such as leek, onion, garlic, beans such as soybeans, groundnuts, green beans, peas, azuki bean, other fruit vegetables such as strawberries, radish, turnip , Straight roots such as carrots, burdock, taro, cassava, potato, sweet potatoes, sweet potatoes, etc., asparagus, spinach, honeybees, etc., eustoma, stock, carnation, chrysanthemum, rice, Cereals such as corn, turf such as bentgrass and sorghum, oil crops such as rapeseed and sunflower Sugarcane crops such as sugarcane and sugar beet, fiber crops such as cotton and rush, feed crops such as clover, sorghum and dent corn, deciduous fruit trees such as apple, pear, grape and peach, citrus orange, lemon Citrus fruits such as grapefruit, woody species such as satsuki, azalea and cedar. Among these, during the cultivation of tomato, pepper, capsicum, eggplant, cucumber, pumpkin, melon, watermelon, celery, parsley, lettuce, leek, onion, asparagus, eustoma, stock, rice, bentgrass, peony, sugar beet, etc. This is particularly effective for plants to be transplanted and for plants that grow by rooting from cuts and cuttings such as chrysanthemum, carnation, satsuki, azalea and grape. Examples of the grass family for the purpose of preventing lodging include rice, wheat, barley, rye, corn and the like. In particular, rice and wheat are sprayed at the time of splitting, so many adventitious roots are generated, the growth of the whole root system is promoted, and the nutrient absorption efficiency is improved, so the plant adventitious root generation inducing agent and root system development promoting agent of the present invention. It is preferable to exhibit 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、発根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。 In addition, 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 such as high planting density, high humidity, lack of sunshine, etc. You may use together with anti- gibberellins (paclobutrazol, uniconazole P, ansimidol, etc.), growth inhibitors (such as daminozide), and ethylene generators (such as ethephon). In cuttings, cuttings, cuttings, and tissue culture, auxin compounds (such as indoleacetic acid, indolebutyric acid, naphthylacetamide, and naphthaleneacetic acid) may be used in combination for the purpose of enhancing rooting induction effects. 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発根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 plant adventitious root generation inducer and root system development accelerator of the present invention can be used in combination or in combination with various insecticides, fungicides, microbial pesticides, fertilizers and the like. In particular, combined use with hydroxyisoxazole, metasulfocarb, metalaxyl and the like, which have been reported to induce rooting in addition to bactericidal action, is effective in combination with bactericides. Mixing with an insecticide that is directly applied to seeds or an insecticide that is used during the seedling stage (thiamethoxam, fludioxonil, metalaxyl, chlorantraniliprole, etc.) is particularly effective.
When used in combination with a fertilizer, the combined use with a seedling fertilizer for the purpose of raising healthy seedlings and the use with a fertilizer applied immediately before transplanting for the purpose of promoting survival are particularly effective. Mixing with a slow-acting fertilizer for the purpose of maintaining the efficacy of the plant growth regulator of the present invention for a long period of time and improving the fertilizer component utilization rate is particularly effective.
次に、試験例、実施例を示して本発明を更に詳細に説明するが、本発明はこれらの実施例に限定されるものではない。
試験例
<1.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1〜22、及びR6に置換基を導入した化合物である6−クロロアントラニル酸(化合物23)及び6−メチルアントラニル酸(化合物24)、R5の置換基としてフッ素原子を導入した化合物である5−フルオロアントラニル酸(化合物25)、R2に隣接する窒素原子にさらに置換基を導入した化合物であるN,N−ジメチルアントラニル酸(化合物26)について蒸留水で希釈し、濃度が0.1mM、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、アズキ発根促進アッセイ(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)succinamicacid analogs. Plant Soil 255: 67-75.)を行った。なお、化合物2のみ0.1mMに代えて0.5mMの溶液を用いた。
アズキ切片は基部を48時間、0.1mM、0.5mM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。なお、各化合物の活性を測定する際に、対照として蒸留水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1に示す。Next, the present invention will be described in more detail with reference to test examples and examples, but the present invention is not limited to these examples.
Test example <1. Confirmation test of adventitious root generation induction by dipping treatment in azuki bean>
A fluorine atom was introduced as a substituent of 6-chloroanthranilic acid (Compound 23) and 6-methylanthranilic acid (Compound 24), which are compounds in which a substituent was introduced into the above compounds 1 to 22 and R 6 , and R 5 a compound which is 5-fluoro-anthranilic acid (compound 25) was diluted with distilled water for N is a compound obtained by introducing a substituent to the nitrogen atom adjacent to R 2, N-dimethyl anthranilic acid (compound 26), concentration A 0.1 mM, 1 mM aqueous solution is prepared and adjusted to pH 7 using dilute hydrochloric acid and aqueous sodium hydroxide solution, and then azuki bean rooting promotion 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) succinamicacid analo gs. Plant Soil 255: 67-75.). In addition, only the compound 2 was replaced with 0.1 mM, and a 0.5 mM solution was used.
The base of the azuki bean was immersed in each test solution of 0.1 mM, 0.5 mM and 1 mM for 48 hours, and the number of adventitious roots generated after 7 days was counted. The number of repetitions was 5. In addition, when measuring the activity of each compound, what was treated with distilled water as a control was cultured, and the number of adventitious roots was similarly measured. For this reason, the control group showed the total average value measured several times.
The test results are shown in Table 1 below.
表1に示すとおり化合物1〜22を含有する溶液は、対照区の不定根発根数と比較すると高い不定根発生誘導作用と発根促進作用が認められた。特に、濃度0.1mMでは化合物5、7、15、17、20、21の化合物が対照である蒸留水に対して200%以上の発根率を示した。また濃度1mMでは1、4、9、10の化合物が対照と比較して200%以上の不定根の発根率を示した。
一方、R6の水素を置換した化合物23、24は発根活性を有さなかった。このためR6の置換は発根のためには好ましくないことが判明した。またR5の置換基をフッ素原子とした場合は発根を抑制した。さらにR2に隣接した水素原子をメチル基に置換した化合物26も発根率は低かった。As shown in Table 1, the solution containing compounds 1 to 22 showed higher adventitious root generation inducing action and rooting promoting action as compared with the number of adventitious root rooting in the control group. In particular, at a concentration of 0.1 mM, compounds 5, 7, 15, 17, 20, and 21 showed a rooting rate of 200% or more with respect to distilled water as a control. At a concentration of 1 mM, compounds 1, 4, 9, and 10 showed rooting rates of adventitious roots of 200% or more compared to the control.
On the other hand, compounds 23 and 24 in which R 6 hydrogen was substituted did not have rooting activity. For this reason, it has been found that substitution of R 6 is not preferred for rooting. In addition, rooting was suppressed when the substituent of R 5 was a fluorine atom. Further, the compound 26 in which the hydrogen atom adjacent to R 2 was substituted with a methyl group also had a low rooting rate.
<2.水稲発芽時のアントラニル酸の根系発達促進効果試験>
イネ科植物は発芽時に主根が伸長し、さらに側根が伸長し、定着後に不定根が発生する。発芽における根系の発育が成長に大きく影響することが知られている。
あらかじめ滅菌した水稲種子3粒を、アントラニル酸(化合物1)を各種濃度で含有させた寒天中に播種し、23℃連続光下で50日間培養したのちに取り出し、根長、根数、草丈を測定した。<2. Root system development promoting effect test of anthranilic acid at the time of rice germination>
In the grass family, the main roots are elongated at germination, the lateral roots are elongated, and adventitious roots are generated after establishment. It is known that the development of root system in germination greatly affects growth.
Three seeds of rice sterilized in advance were sown in agar containing anthranilic acid (compound 1) in various concentrations, cultured for 50 days under continuous light at 23 ° C, taken out, and the root length, number of roots, and plant height were determined. It was measured.
取り出したイネの状態の画像を図1に示す。目視観察では明らかにアントラニル酸を配合した場合根系が発達していた。
また根長の測定結果を図2、根数の計数結果を図3に示す。アントラニル酸0.01mM、0.03mM添加では根長が伸張しており、根数は0.1mM添加で増加していた。さらに草丈の測定結果を図4に示す。草丈はアントラニル酸の添加量が増加するにしたがって伸長し、草丈の生育が良くなっていることが確認された。アントラニル酸は根系の発達に寄与し、その結果草丈が伸長したものと評価した。An image of the extracted rice state is shown in FIG. By visual observation, the root system was clearly developed when anthranilic acid was added.
FIG. 2 shows the measurement results of the root length, and FIG. 3 shows the count results of the number of roots. When anthranilic acid was added at 0.01 mM and 0.03 mM, the root length was extended, and the number of roots was increased when 0.1 mM was added. Furthermore, the measurement result of plant height is shown in FIG. The plant height increased as the amount of anthranilic acid increased, and it was confirmed that the plant height grew better. Anthranilic acid contributed to the development of the root system, and as a result, the plant height was evaluated to be elongated.
<3.葉面散布、根茎散布によるデントコーンの不定根増加効果試験>
化合物14の5−クロロアントラニル酸の10mM水溶液を生育途上(播種後3週間)のデントコーンに1か月間に4回、葉面及び株元に散布し、播種後4か月後に根を掘り出して状態を観察した。観察時の画像を図6に示す。対照の無散布に比較して根張りの面積が広く、根数も顕著に増加していた。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、トウモロコシの不定根の発生を誘導し、根系全体の発達を促進していた。その結果、非常に引き抜きに対して抵抗性が強く、倒伏に対する効果があるものと評価できた。<3. Adventitious root increasing effect test of dent corn by foliar application and rhizome application>
A 14 mM 5-chloroanthranilic acid 10 mM aqueous solution of compound 14 is sprayed onto the dent corn during growth (3 weeks after sowing) 4 times a month on the foliage and the plant, and the roots are dug 4 months after sowing. Was observed. An image at the time of observation is shown in FIG. Compared to the non-sprayed control, the area of rooting was wide and the number of roots was also significantly increased. The plant adventitious root development inducing agent and root system development promoting agent of the present invention induced the occurrence of adventitious roots in corn and promoted the development of the entire root system. As a result, it was evaluated that it was very resistant to pulling and had an effect on lodging.
<4.根元散布によるキュウリの根系発達促進効果試験>
キュウリ品種オーシャン((株)埼玉原種育成会)を培養土「すくすく倶楽部30」(雪印種苗(株))を充填した直径9cmのポットに播種し、温室内で生育させた。播種後14日目から1週間に1回、化合物1のアントラニル酸を1mM、10mMの濃度で1ポット当たり30mLずつ根元に散布した。また、対照区には水を30mLずつ同様に根元に散布した。
播種後35日後に2個体×2反復をサンプリングし、根部をよく水洗した後に総根長をルートスキャナー(Comair社製)で測定した。また、葉面積を自動葉面積計(林電工(株))によって測定した。その後、根部と葉部・茎部を通風乾燥した後、さらに乾燥物の重量を測定し、乾物重量とした。
それぞれ4サンプル測定の平均値を下記の表2に示した。なお表中の括弧内の数値は、対照区を100とした場合の相対値を%で示したものである。10mM区において総根長の増加が認められ、すべての処理区において根部乾物重量の増加も認められた。また、葉面積の増加も認められた。
したがってアントラニル酸は根系を発達させ、さらに葉及び茎の成長を促進することが明らかとなった。また市販の培養土を用いた育苗において、発根を促進するため、早期に生育の良好な苗を得る目的に適していることが明らかとなった。<4. Root system development promoting effect test of cucumber by root spraying>
The cucumber variety Ocean (Saitama Hara Seed Breeding Society) was sown in a 9 cm diameter pot filled with the culture soil “Sukusuku Club 30” (Yukirushi Seedling Co., Ltd.) and grown in a greenhouse. From the 14th day after seeding, once per week, anthranilic acid of Compound 1 was sprayed at the root of 30 mL per pot at a concentration of 1 mM and 10 mM. In the control group, 30 mL of water was similarly applied to the roots.
Two days × 2 repeats were sampled 35 days after sowing, and after thoroughly washing the roots with water, the total root length was measured with a root scanner (Comair). The leaf area was measured with an automatic leaf area meter (Rinden Electric Co., Ltd.). Then, after the root part and the leaf part / stem part were air-dried, the weight of the dried product was further measured to obtain the dry matter weight.
The average values of the four sample measurements are shown in Table 2 below. The numerical values in parentheses in the table indicate relative values in% when the control group is 100. An increase in total root length was observed in the 10 mM group, and an increase in root dry matter weight was also observed in all treatment groups. An increase in leaf area was also observed.
Thus, it became clear that anthranilic acid develops the root system and further promotes leaf and stem growth. In addition, it became clear that it is suitable for the purpose of obtaining seedlings with good growth at an early stage in order to promote rooting in seedlings using commercially available culture soil.
<5.根元散布によるトウモロコシの根系発達促進効果試験>
トウモロコシ品種アシル(雪印種苗(株))を培養土「すくすく倶楽部30」(雪印種苗(株))を充填した直径9cmのポットに播種し、温室内で生育させた。播種後20日目から50日間、1週間に3回、化合物1のアントラニル酸0.1mM、1mMの濃度の水溶液を1ポット当たり30mLずつ根元に散布した。また、対照区には、1ポット当たり水を30mLずつ根元に散布した。
播種後80日後に3個体×2反復をサンプリングし、根部をよく水洗した後に総根長をルートスキャナー(Comair社製)で測定した。その後、根部と葉部・茎部を通風乾燥した後、さらに乾燥物の重量を測定し、乾物重量とした。
それぞれ6サンプル測定の平均値を下記の表3に示した。なお表中の括弧内の数値は、対照区を100とした場合の相対値を%で示したものである。すべての処理区においてトウモロコシ総根長の増加が認められた。また、アントラニル酸1mM区では根部乾物重の顕著な増加が確認できた。
したがってアントラニル酸の根元散布でトウモロコシの根系発達が促進されることが明らかとなった。<5. Root system development promoting effect test of corn by root spray>
Corn cultivar acyl (Snow Brand Seed Co., Ltd.) was sown in a 9 cm diameter pot filled with culture soil “Sukusuku Club 30” (Snow Brand Seed Seed Co., Ltd.) and grown in a greenhouse. From the 20th day after sowing, 30 mL of anthranilic acid 0.1 mM and 1 mM aqueous solutions of Compound 1 were sprayed on the root for 3 days a week for 50 days. In the control group, 30 mL of water per pot was sprayed at the base.
Three days × 2 repeats were sampled 80 days after sowing, and after thoroughly washing the roots with water, the total root length was measured with a root scanner (manufactured by Comair). Then, after the root part and the leaf part / stem part were air-dried, the weight of the dried product was further measured to obtain the dry matter weight.
The average values of 6 sample measurements are shown in Table 3 below. The numerical values in parentheses in the table indicate relative values in% when the control group is 100. An increase in total corn root length was observed in all treatment areas. In addition, in the 1 mM section of anthranilic acid, a significant increase in root dry matter weight could be confirmed.
Therefore, it became clear that the root system development of maize is promoted by the root application of anthranilic acid.
<6.培地添加によるシロイヌナズナの不定根誘導効果試験>
化合物1のアントラニル酸・化合物15のクロロアントラニル酸をそれぞれ混合した1/2MS固形培地(MS培地粉末(日本製薬)を既定の1/2濃度とし、ゲランガム0.3%、ショ糖1%を加え、滅菌したもの)にシロイヌナズナ野生型Col―0を播種し、2日間の暗所低温処理後、インキュベータ内(温度22℃、明期16時間・暗期8時間の長日条件)で12日間生育させ、生じた不定根の数を計測した。4個体の平均値とした。
それぞれ4個体を測定した平均値を下表4に示す。
無添加である対照区では不定根の発生はまったく認められなかったが、培地中へのアントラニル酸30μM添加区、5−クロロアントラニル酸10μM添加区では不定根の発生が認められた。
したがって、植物育成用の培地にあらかじめアントラニル酸を添加しておいても、不定根の誘導が促進されることが明らかとなった。<6. Adventitious root induction effect test of Arabidopsis thaliana by medium addition>
1 / 2MS solid medium mixed with anthranilic acid of compound 1 and chloroanthranilic acid of compound 15 (MS medium powder (Nippon Pharmaceutical Co., Ltd.) is set to a predetermined half concentration, and 0.3% gellan gum and 1% sucrose are added. Sterilized) seeded with Arabidopsis wild-type Col-0, grown in an incubator (temperature 22 ° C, light period 16 hours, dark period 8 hours long-day condition) after 2 days in the dark at low temperature. And the number of adventitious roots produced was counted. The average value of 4 individuals was used.
The average value obtained by measuring 4 individuals is shown in Table 4 below.
In the control group without addition, adventitious roots were not observed at all. However, adventitious roots were observed in the group added with 30 μM anthranilic acid and 10 μM 5-chloroanthranilic acid.
Therefore, it has been clarified that induction of adventitious roots is promoted even if anthranilic acid is added to the plant growth medium in advance.
<7.アズキ切り口浸漬処理におけるアントラニル酸とL−トリプトファンとの不定根誘導作用の比較>
化合物1であるアントラニル酸とL−トリプトファンを蒸留水で希釈し、濃度が1mMおよび2mMの水溶液を調製し、水酸化ナトリウム水溶液を用いてpH7とした。これらの被検液について試験例1と同様にアズキ発根促進アッセイを行った。
試験結果を表5に示す。<7. Comparison of adventitious root-inducing action of anthranilic acid and L-tryptophan in azuki bean cutting immersion treatment>
Anthranilic acid as compound 1 and L-tryptophan were diluted with distilled water to prepare aqueous solutions having concentrations of 1 mM and 2 mM, and the pH was adjusted to 7 using an aqueous sodium hydroxide solution. These test solutions were subjected to azuki bean root promotion assay in the same manner as in Test Example 1.
The test results are shown in Table 5.
従来、アントラニル酸はトリプトファンに代謝され、さらにインドール−3−酢酸に変換されることにより発根誘導するといわれていた(非特許文献3)。しかしながら、表5に示す通り、アントラニル酸の不定根誘導作用はいずれの濃度においてもトリプトファンよりも高かった。このことから、不定根誘導に関してはアントラニル酸そのものが活性を有することが明らかとなった。 Conventionally, it has been said that anthranilic acid is metabolized to tryptophan and further converted to indole-3-acetic acid to induce rooting (Non-patent Document 3). However, as shown in Table 5, the adventitious root-inducing action of anthranilic acid was higher than that of tryptophan at any concentration. From this, it became clear that anthranilic acid itself has activity for adventitious root induction.
Claims (15)
(ただし、(式1)のR1〜R6は次のいずれかの構造である。
R1= ヒドロキシ基、アルコキシ基、又はアミノ基
R2= 水素原子、アルキル基、フェニル基又はアシル基
R3= 水素原子、水酸基、ハロゲン原子、アルキル基又はアルコキシ基
R4= 水素原子、ハロゲン原子、アミノ基、カルボキシル基
R5= 水素原子、アルキル基、ハロゲン原子又はニトロ基
R6= 水素原子)。Plant adventitious root development inducer and root system development promoter comprising a compound represented by the following (formula 1) or a salt or ester thereof:
(However, R < 1 > -R < 6 > of (Formula 1) is one of the following structures.
R 1 = hydroxy group, alkoxy group, or amino group R 2 = hydrogen atom, alkyl group, phenyl group or acyl group R 3 = hydrogen atom, hydroxyl group, halogen atom, alkyl group or alkoxy group R 4 = hydrogen atom, halogen atom Amino group, carboxyl group R 5 = hydrogen atom, alkyl group, halogen atom or nitro group R 6 = hydrogen atom).
請求項1記載の植物の不定根発生誘導剤及び根系発達促進剤。The alkoxy group of R 1 is a methoxy group, the alkyl group of R 2 is a methyl group or an ethyl group, the alkoxy group is a methoxy group, the halogen atom of R 3 is chlorine or bromine, the halogen atom of R 4 is chlorine, and the alkyl of R 5 The group is a methyl group and the halogen atom is chlorine, bromine, or iodine,
The plant adventitious root development inducer and root system development promoter of Claim 1.
An agrochemical containing the plant adventitious root generation inducer and root system development promoter according to claim 13.
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