JPS5885806A - Plant growth regulator - Google Patents

Plant growth regulator

Info

Publication number
JPS5885806A
JPS5885806A JP18396781A JP18396781A JPS5885806A JP S5885806 A JPS5885806 A JP S5885806A JP 18396781 A JP18396781 A JP 18396781A JP 18396781 A JP18396781 A JP 18396781A JP S5885806 A JPS5885806 A JP S5885806A
Authority
JP
Japan
Prior art keywords
beta
glucopyranosyl
plant growth
growth regulator
glycoside
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP18396781A
Other languages
Japanese (ja)
Inventor
Junichi Iwamura
淳一 岩村
Koichiro Komai
功一郎 駒井
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KINKIDAIGAKU
Original Assignee
KINKIDAIGAKU
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by KINKIDAIGAKU filed Critical KINKIDAIGAKU
Priority to JP18396781A priority Critical patent/JPS5885806A/en
Publication of JPS5885806A publication Critical patent/JPS5885806A/en
Pending legal-status Critical Current

Links

Abstract

PURPOSE:A plant growth regulator of a terpene glycoside that shows activities of growth stimulation, blooming and dormancy breaking, which gibberellin has, and causes no yellowing as well as root growth inhibition, futher being stable, soluble in water, readily and inexpensively available. CONSTITUTION:The objective plant growth regulator contains, as an active ingredient, a glycoside containing stevoil as an aglicone, preferably a diterpene glycoside of the formula (R1 is H, metal ion and R2 is beta-glucopyranosyl, or R1 is beta-glucopyranosyl and R2 is beta-glucopyranosyl or R1 is beta-glucopyranosyl and R2 is H) such as 13-O-beta-glucosylsteviol. USE:It can be applicable to grape, persimmon, strawberry, honewort, butterbur, celery, tomato, cucumber, tulip, blettila and hinoki cypress.

Description

【発明の詳細な説明】 本発明は、ジベルリン様活性を示すジテルペン配糖体の
少なくとも一種を有効成分とする植物生長調整剤に関す
る。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a plant growth regulator containing at least one diterpene glycoside exhibiting diberin-like activity as an active ingredient.

シヘレリン様活性を示すものに多数のジベレリン類が知
られ、なたでもジベレリンA8.A7.A3o。
Many gibberellins are known to exhibit cihererin-like activity, including gibberellin A8. A7. A3o.

A3□はその活性の強さでも良く知られ、とくにジベレ
リンA3は実用に供されている。しかし、これらの化合
物は植物の伸長を促進するという性質を有するが、一方
では実用濃度で貧化を起し、根の発育を阻害し、また水
に難溶などの欠点があり、効果が不充分であるというこ
とがしばしば指摘さ ”nていた。
A3□ is well known for its strong activity, and gibberellin A3 in particular is in practical use. However, although these compounds have the property of promoting plant elongation, they also have drawbacks such as causing starvation at practical concentrations, inhibiting root development, and being poorly soluble in water, making them ineffective. It is often pointed out that enough is enough.

本発明者らは、鋭意研究を重ねた結果、ジベレリン類の
有する生理作用:1)生長促進効果、2)開花に対する
効果、8)休眠打破、発芽に対する作用、4)単為結実
の促進効果、5)加水分解酵素の賦活・化などの活性を
示すと共に、ジベレリン類とは異なり、貧化を起したり
根の発育を阻害することなく、物性的に安定で水溶性で
、入手が容易でかつ安価な植物生長調整剤を開発するこ
とに成功した。この有効成分は、ジテルペン配糖体であ
る。このような配糖体が有効なことは、ジベレリン配糖
体がhとんど不活性であること(CrozierA、、
 C1C0Kuo、 R8C,Durl ey st 
RoP、Pharis ; Can、 J、 Bot、
As a result of extensive research, the present inventors have found that gibberellins have physiological effects: 1) Growth promoting effect, 2) Effect on flowering, 8) Effect on breaking dormancy and germination, 4) Effect on promoting parthenocarpy. 5) In addition to exhibiting activities such as activating and converting hydrolytic enzymes, unlike gibberellins, it does not cause anemia or inhibit root growth, is physically stable, water-soluble, and easily available. We also succeeded in developing an inexpensive plant growth regulator. The active ingredient is a diterpene glycoside. The effectiveness of such glycosides is due to the fact that gibberellin glycosides are mostly inactive (Crozier A,
C1C0Kuo, R8C, Durl ey st
RoP, Pharis; Can, J., Bot;
.

48 867(1970)Eカ)ら、ジベレリン類への
ゲルコピフッシル基の導入はジベレリン不活性機構と関
係があると示唆されていたことからして意外なことであ
る。
48 867 (1970) E. et al. et al. suggested that the introduction of a gelcopifusyl group into gibberellins is related to the gibberellin inactivation mechanism.

かくして、本発明は、式(■): 〔式中、Roが水素原子又は金属イオンで、R2がβ−
クルコビラノシルi;R1がβ−グルコピラノシル基で
、R2がβ−グルコピラノシル基;又1dR1がβ−グ
ルコピラノシル基で、R2が水素である。〕 で示されるジテルペン配糖体の少なくとも一種を有効成
分とする植物生長調整剤を提供するものである。
Thus, the present invention provides formula (■): [wherein Ro is a hydrogen atom or a metal ion, and R2 is β-
Curcobyranosyl i: R1 is a β-glucopyranosyl group, R2 is a β-glucopyranosyl group; 1dR1 is a β-glucopyranosyl group, and R2 is hydrogen. ] The present invention provides a plant growth regulator containing at least one of the diterpene glycosides shown below as an active ingredient.

上記弐山の化合物は、実質的に公知物質で、公知の方法
によって得ることができるものである。
The above-mentioned Niyama compound is substantially a known substance and can be obtained by a known method.

すなわち、ステビオールを真性アグリコンとする配糖体
を含有する、例えば覆盆子、ヌテビア(Stervia
 rebaudiana )等の葉から抽出単離するか
、その単離物を部分加水分解するかあるいは常法に従っ
て塩に導くことによって得ることができる〔参照文献: (1)  H,Bow)od、R,A11erton、
HWDiehland、HoG、Fl−etcher、
 J、Org、Chern、、 2.、.0 、875
(195j)。
That is, plants containing glycosides with steviol as the true aglycone, such as Steviol, Nutevia (Stervia), etc.
rebaudiana), or by partially hydrolyzing the isolated product or converting it into a salt according to a conventional method [References: (1) H, Bow) od, R, A11erton,
HWDiehland, HoG, Fl-etcher,
J, Org, Chern, 2. ,.. 0,875
(195j).

(21H,Kohda、R,Kasai、に、Yama
saki、に0Murakami、00Tanaka、
Phytochanistry、 15 、 ggl 
(1R76)。
(21H, Kohda, R, Kasai, Yama
saki, ni0Murakami, 00Tanaka,
Phytochanistry, 15, ggl
(1R76).

(31M、Kobayasbi 、 S、 l[−br
ikawa 、 I、 H,Degrandi 、 J
 。
(31M, Kobayasbi, S, l[-br
ikawa, I., H., Degrandi, J.
.

Veno 、 HoMi tsuHashi 、 Ph
ytochemi 5try 、 l 6.14 Q 
5(1977)。
Veno, HoMitsuHashi, Ph
ytochemi 5try, l 6.14 Q
5 (1977).

(4)  1.、Sakamoto、に、Yamasa
ki、O,Tanaka、Chem。
(4) 1. , Sakamoto, ni, Yamasa
ki, O, Tanaka, Chem.

Pharm、Bull、、  25. 844  (1
977)。
Pharm, Bull, 25. 844 (1
977).

(5)  守田豊重、藤田功、岩村淳−9特許公報、昭
52−27226゜ (6)  上野純子、三橋博、住田哲也9日本薬学会第
96回講演要旨集第2分冊、254  (1976)、
)ヌテビアの葉からの抽出単離の1例を示すと、まず乾
燥葉を温水抽出に付し、極性溶媒(例えばメタノール)
次いで水洗した分子ふるい効果を有する樹脂(例えばア
ンバーライ)XAD−2)に上記抽出物を通し、次に水
を通して脱塩あるいは低分子化合物を溶出させ、極性溶
[(例えばメタノール)で配糖体を溶離させる。この溶
M液を濃縮すると、白色あるいは淡黄色の粉末が得られ
る。
(5) Toyoshige Morita, Isao Fujita, Jun Iwamura-9 Patent Publication, 1972-27226゜ (6) Junko Ueno, Hiroshi Mitsuhashi, Tetsuya Sumita 9 Collected Abstracts of the 96th Meeting of the Pharmaceutical Society of Japan, Volume 2, 254 (1976) ,
) To give an example of extraction and isolation from Nutevia leaves, dry leaves are first subjected to hot water extraction and extracted with a polar solvent (e.g. methanol).
Next, the above extract is passed through a water-washed resin having a molecular sieving effect (e.g., Amberly XAD-2), and then water is passed to desalt or elute low-molecular-weight compounds. elute. When this solution M is concentrated, a white or pale yellow powder is obtained.

これを再結晶あるいはカラムクロマトグラフィーに付す
ことにより各種のジテルペン配糖体に単離することがで
きる。
Various diterpene glycosides can be isolated by subjecting this to recrystallization or column chromatography.

lfc式(Ilでに0が水素原子の化合物は、常法によ
り対応する塩(ことに金属塩)に導くことができる。好
ましい塩としては、ナトリウム塩、カリウム塩、リチウ
ム塩などのアルカリ金属塩であり、これらは水溶性であ
る。塩の他の例としては、カルシウム塩、マグネシウム
塩などのアルカリ土類金属塩が挙げられる。
A compound of the lfc formula (Il in which 0 is a hydrogen atom) can be converted into a corresponding salt (particularly a metal salt) by a conventional method. Preferred salts include alkali metal salts such as sodium salts, potassium salts, and lithium salts. and these are water-soluble.Other examples of salts include alkaline earth metal salts such as calcium salts and magnesium salts.

本発明の有効成分は、一種類又は二種類以上の混合物で
あってもよい。特に好ましい有効成分として[,1B−
0−β−グにコシルヌテピオール〔式(Ilにおいてに
0が水素原子で、R2がβ−グルコピラノシル基である
もの〕のナトリウムまたはカリウム塩、デモノグルコシ
ルステビオシド〔式(I)においてR1がβ−グルコピ
ラノシル基で、R2がβ−グルコピラノシル基であるも
の〕が挙げられる。
The active ingredients of the present invention may be one type or a mixture of two or more types. A particularly preferred active ingredient is [,1B-
0-β-g is the sodium or potassium salt of cosylnutepiol [formula (in which 0 is a hydrogen atom and R2 is a β-glucopyranosyl group]), demonoglucosylstevioside [formula (I) in which R1 is β-glucopyranosyl group] -glucopyranosyl group in which R2 is a β-glucopyranosyl group].

本発明の有効成分は、使用時に通常水性溶液として用い
られる。なお、有効成分は予め固体の賦形剤で粉末剤゛
や顆粒剤とし、片時水性溶液としてもよい。また比較的
高濃度の水性溶液とし、使用時に希釈してもよい。水性
溶液とするには、通常水のみで十分である。しかし場合
によV(例えば有効成分が水に難溶性のとき)適当な界
面活性剤を加え水性懸濁液又は水性分散液の形状にして
もよい。
The active ingredient of the present invention is usually used as an aqueous solution. The active ingredient may be prepared in advance as a powder or granules using a solid excipient, and then may be temporarily prepared as an aqueous solution. Alternatively, it may be prepared as a relatively highly concentrated aqueous solution and diluted at the time of use. Water alone is usually sufficient to form an aqueous solution. However, in some cases (for example, when the active ingredient is poorly soluble in water) a suitable surfactant may be added to form an aqueous suspension or dispersion.

使用時における有効成分の濃度は、0.001〜0.2
重量%が好ましい。
The concentration of the active ingredient during use is 0.001 to 0.2
Weight percent is preferred.

また、本発明の植物生長1整剤には、他の植物生長調整
作用を有する化合物(例えばジベレリン)や植物に対す
る栄養源を含有させてもよい。
Further, the plant growth regulating agent 1 of the present invention may contain other compounds having a plant growth regulating effect (for example, gibberellin) and a nutrient source for plants.

このようにして得られた製剤は植物に対して優れた生長
調整作用を示す。
The preparation thus obtained exhibits an excellent growth regulating effect on plants.

使用法は、゛ジベレリン製剤のそれに準拠して用いるこ
とが好ましい。
It is preferable to use it in accordance with that for gibberellin preparations.

また本発明の植物生長調整剤が適用される対象植物は特
に限足されないが、具体的には次のような農作植物が挙
代られる。
Further, target plants to which the plant growth regulator of the present invention is applied are not particularly limited, but specifically, the following agricultural plants can be mentioned.

すなわち、ぶどう類、かき類、いちご類などの果物類;
みつば類、はうれん草、セロリ−1ふき、春うど、トマ
ト、きうり、なす等の野菜類;シクラメン、プリムラ、
みやこわ丁れ、夏菊、シフン、チューリップ、テラポウ
ユリなどの花弁植物類漬杉類、ヒノキ類などの樹木類で
ある。
i.e. fruits such as grapes, oysters, strawberries;
Vegetables such as honeysuckle, spinach, celery - 1 fuki, spring noodles, tomatoes, cucumbers, eggplants; cyclamen, primula,
These include petal plants such as Miyakowa clover, summer chrysanthemum, chrysanthemum, chrysanthemum, tulip, and terrapin lily, and trees such as pickled cedar and cypress.

また本発明の植物生長調整剤の使用目的としては、果物
類の無種子化、熟期促進、果粒肥大、果房伸長促進、落
果防止、着果数増大など;野菜類の生育促進、肥大促進
、休眠打破による生育促進、空洞果防止、果実肥大、着
果数増大など;花弁植物類の開花促進、草丈伸長促進、
休眠打破など;及び樹木類の花芽分化促進などが挙げら
れる。
In addition, the purposes of use of the plant growth regulator of the present invention include making fruits seedless, accelerating ripening, enlarging fruit grains, promoting fruit cluster elongation, preventing fruit drop, and increasing the number of fruit set; promoting growth and enlargement of vegetables. promotion, growth promotion by breaking dormancy, prevention of hollow fruit, fruit enlargement, increase in number of fruit set, etc.; promotion of flowering of petal plants, promotion of plant height elongation,
Examples include breaking dormancy; and promoting flower bud differentiation in trees.

ことに次のような利用用途が挙げられる。In particular, the following uses can be mentioned:

(1)  柑橘果実、その他果菜類の収穫時期及び熟成
期間を調整する用途。
(1) Use to adjust the harvest time and ripening period of citrus fruits and other fruits and vegetables.

(2)礫耕、水耕などの施設園芸に依存しているそ菜類
の生育促進の用途。
(2) Applications for promoting the growth of vegetables that rely on greenhouse horticulture such as gravel cultivation and hydroponics.

(3)花弁園芸植物の開花調節剤としての用途。(3) Use as a flowering regulator for petal garden plants.

(4)千本科植物、特にイネの育苗時における生長調節
用途(機械植え育苗への適応)。
(4) Use for growth regulation in raising seedlings of plants of the Senbonaceae family, especially rice (adaptation to mechanical seedling raising).

(5)種子休眠の覚醒作用により雑草を一挙に発芽させ
ておいて除草剤を用いて除草する除草助剤としての用途
(5) Use as a weeding aid for weeding by causing weeds to germinate all at once due to the awakening effect of seed dormancy, and then weeding using a herbicide.

次に実施例を挙げて本発明を説明する。Next, the present invention will be explained with reference to Examples.

実施例1(生長促進効果) 表1の各化合物の100.200.500およびioo
Example 1 (growth promoting effect) 100.200.500 and ioo of each compound in Table 1
.

PPmの濃度の水溶液を作製した。50−のサンフ。An aqueous solution with a concentration of PPm was prepared. 50-sanf.

ル瓶(φB2111+1Xh65M)に同径の沖紙を敷
き、その上にイネの囃性品種であるタンギンホース゛(
Oryza 5aliva L+var Tangin
bozu )の種子全100個づつ並べておいて、これ
に上記各水溶液を2−づつ投与し、25°C1約300
0/uxの恒温器内で14日間育成を行なった。この期
間中の水の補給は、蒸留水を適宜に与えた。生育の状態
は葉茎部の丈を測定し、その結果を表1に示す。
Place a sheet of paper with the same diameter in a bottle (φB2111+1Xh65M), and place Tanginhose (a rice variety with a dry taste) on top of it.
Oryza 5aliva L+var Tangin
A total of 100 seeds of Bozu (Japanese bozu) were lined up, 2 doses of each of the above aqueous solutions were administered to them, and the seeds were heated at 25°C at about 300°C.
The cells were grown for 14 days in a thermostat at 0/ux. Water was supplied with distilled water ad libitum during this period. The growth status was determined by measuring the height of the leaf and stem, and the results are shown in Table 1.

実施例1のタンギンポーズを肉眼的に観察した結果では
、いずれの配糖体も各濃度においてジベレリン製剤で観
察されるような貧化現象は観察されず、対照群となんら
・有意差は観察されなかつよ。
As a result of macroscopic observation of the tangine pose in Example 1, no depletion phenomenon observed with gibberellin preparations was observed at each concentration of any of the glycosides, and no significant difference was observed from the control group. Yo.

また、実施例1における発根に対する効果を根の長さに
よV観察した結果を表2に示した。結果より明らかなよ
うにジベレリン製剤で見られるような発根阻害は観察さ
れなかった。
Further, Table 2 shows the results of observing the effect on rooting in Example 1 according to root length. As is clear from the results, inhibition of rooting as seen with gibberellin preparations was not observed.

Claims (1)

【特許請求の範囲】 17ヌテビオールを真性アグリコンとする配糖体の少な
くとも一種を有効成分とする植物生長調整剤。 2、配糖体が式(■): 〔式中、R1が水素原子又は金属イオンで、R2がβ−
グルコピラノシル基;R1がβ−グルコピラノシル基で
、R2がβ−グルコピラノシル基;又はR1がβ−グル
コピラノシル基で、R2が水素である。〕 で示されるジテルペン配糖体である特許請求の範囲第1
項記載の植物生長調整剤。 8、式(11においてR1が水素原子、ナトリウム原子
又はカリウム原子で、R2がβ−グルコピラノシル基で
ある特許請求の範囲第2項記載の植物生長調整剤。
[Scope of Claims] A plant growth regulator containing at least one type of glycoside having 17 nuteviol as a true aglycone as an active ingredient. 2. The glycoside has the formula (■): [In the formula, R1 is a hydrogen atom or a metal ion, and R2 is β-
Glucopyranosyl group; R1 is a β-glucopyranosyl group, R2 is a β-glucopyranosyl group; or R1 is a β-glucopyranosyl group, and R2 is hydrogen. ] Claim 1 is a diterpene glycoside represented by
The plant growth regulator described in Section 1. 8. The plant growth regulator according to claim 2, wherein R1 in formula (11) is a hydrogen atom, sodium atom, or potassium atom, and R2 is a β-glucopyranosyl group.
JP18396781A 1981-11-16 1981-11-16 Plant growth regulator Pending JPS5885806A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP18396781A JPS5885806A (en) 1981-11-16 1981-11-16 Plant growth regulator

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP18396781A JPS5885806A (en) 1981-11-16 1981-11-16 Plant growth regulator

Publications (1)

Publication Number Publication Date
JPS5885806A true JPS5885806A (en) 1983-05-23

Family

ID=16144950

Family Applications (1)

Application Number Title Priority Date Filing Date
JP18396781A Pending JPS5885806A (en) 1981-11-16 1981-11-16 Plant growth regulator

Country Status (1)

Country Link
JP (1) JPS5885806A (en)

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