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JPH0533201B2 - - Google Patents
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JPH0533201B2 - - Google Patents

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Publication number
JPH0533201B2
JPH0533201B2 JP59028248A JP2824884A JPH0533201B2 JP H0533201 B2 JPH0533201 B2 JP H0533201B2 JP 59028248 A JP59028248 A JP 59028248A JP 2824884 A JP2824884 A JP 2824884A JP H0533201 B2 JPH0533201 B2 JP H0533201B2
Authority
JP
Japan
Prior art keywords
growth
present
roots
leaves
group
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.)
Expired - Lifetime
Application number
JP59028248A
Other languages
Japanese (ja)
Other versions
JPS60172903A (en
Inventor
Jiro Harada
Akira Yamamoto
Katsuya Nigimura
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.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
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 Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Priority to JP2824884A priority Critical patent/JPS60172903A/en
Publication of JPS60172903A publication Critical patent/JPS60172903A/en
Publication of JPH0533201B2 publication Critical patent/JPH0533201B2/ja
Granted legal-status Critical Current

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は植物の生育抑制剤に関し、特には植物
の根の生育をほとんど阻害しないで葉茎の生育の
みを抑制する特殊な生理活性を有する生育抑制剤
の提供を目的とするものである。 従来より植物の生育阻害剤としては、除草剤を
はじめ数多くの化合物が知られているが、それら
のほとんどは植物の根と葉茎の両方の生育を阻害
するか、もしくは根の方を先に生育阻害し枯死さ
せるものである。しかしながら、目的によつては
葉茎の生育のみを抑制し、根の生育を阻害しない
ような植物の生育抑制剤が要望される。たとえば
稲の倒伏防止や健苗育成、ゴルフ場や庭園の芝、
鉄道のまくら木近くの雑草などに関しては、根は
健全にしつかりと生育し他方葉茎はあまり高くな
らない(あまり成長しない)ことが望まれる。 このような目的に応えることができるいわゆる
生育抑制剤としては、従来、よいものが知られて
おらず、このことから比較的少量の使用で効果が
高く、経済的でかつ毒性のない安全性の高い生育
抑制剤の開発が望まれている。 本発明者らはセリ、パセリの抽出物を研究中
に、稲苗の根の生育を阻害しないで葉茎の生育を
抑制する物質を見い出し、その周辺を広く検討し
たところ、芳香族環にアリル基(−CH2CH=
CH2)もしくはイソアリル基(−CH=CHCH3
メチレンジオキシ基(−OCH2O−)とメトキシ
基(−OCH3)とが結合した芳香族化合物が植物
に対して上記した特殊な生理活性を示すことを確
認し本発明を完成した。 すなわち、本発明は1−アリル−2,5−ジメ
トキシ−3,4−メチレンジオキシベンゼン(一
般名:アピオール)、1−プロペニル−2,5−
ジメトキシ−3,4−メチレンジオキシベンゼン
(同:イソアピオール)、1−アリル−2,3−ジ
メトキシ−4,5−メチレンジオキシベンゼン
(同:ジルアピオール)または1−アリル−3−
メトキシ−4,5−メチレンジオキシベンゼン
(同:ミリスチシン)を有効成分とする植物の育
成抑制剤を提供するものである。 本発明にかかわる上記化合物は、容易に入手調
達することができ、微量で前記した特殊な生理活
性を顕著に示し、かつ食用植物の精油の構成成分
でもあり、安全性がきわめて高いという利点を有
する。 本発明にかかわる上記化合物を具体的に示せ
ば、つぎのとおりである。 アピオールおよびその異性体(アルケニルジ
メトキシメチレンジオキシベンゼン類: アピオール イソアピオール ジルアピオール ミリスチシン(アリルメトキシメチレンジオ
キシベンゼン類): ミリスチシン 本発明においては、前記化合物がアリル基もし
くはイソアリル基とメチレンジオキシ基とメトキ
シ基を有することが必要であり、いずれか一つの
基を欠くものでは本発明の目的とする特殊な生理
活性を十分に発揮することはできない。たとえば
2,3,4,5−テトラメトキシアリルベンゼ
ン、アネトール、アイゲノールなどはアリル基
を、またヘリオトロピンはメチレンジオキシ基を
それぞれ有しているが、これらは1分子中に両方
の基を有するものではないため、かかる生理活性
はなく、根の生育の阻害効果の方が大きい。また
桂皮酸も効果はない。 本発明によれば前記した化合物の微量を植物に
施用するこで、根の生育を阻害することはほとん
どなく、葉茎の生育を抑制する効果が得られるた
め、稲の倒伏防止や健苗育成に有効であるほか、
芝の葉の生育を抑えるので、芝刈の回数を大幅に
減少させることができる。さらには鉄道のまくら
木を支えている土手の雑草はその根がはびこるこ
とにより土手の補強効果が期待されるが、この雑
草の葉丈があまりに伸びると刈取りの必要性が生
じるのみならず、晩夏から秋にかけて火災の危険
性が生じるので、このような雑草については根を
健全に保持して葉茎の成長のみを抑制することは
きわめて有益なことである。しかしこのような目
的は通常の除草剤を用いることでは達成されな
い。 本発明を実施するには、前記化合物を水に溶解
もしくは分散させ、通常10〜100ppm程度の濃度
のものとして対象植物に散布すればよい。なお、
溶剤で希釈したり乳化剤等を併用してもよいし、
また該化合物は徐徐に放出させるように製剤化し
て使用してもよい。 つぎに本発明を実施例により説明する。 実施例 1 内径27mm、長さ118mmの管ビンに、1.5gのセル
ロースパウダーを底部に詰め、これに第1表に示
した芳香族化合物を所定濃度で水に溶解もしくは
均一に分散させた水性液を6ml加え試験床を調製
した。 つぎに、これらの管ビンにあらかじめ同じ条件
で調製しておいた1mm出芽した水稲(品種:短銀
坊主)種子を各々6個ずつ置床した後、3000ルツ
クス照射30℃の条件下に12日間保つた。 この後、それぞれの苗の第二葉鞘(LS)と最
長の根の長さ(R)を測定することにより、化合
物の苗の生育に及ぼす影響を調べた。なお、化合
物を加えない水だけ6mlを加えて同条件で生育さ
せ、苗の第二葉鞘(LS)と最長の根の長さ(R)
を求め、これに対するそれぞれの生育阻害率
〔LS阻害率、R阻害率〕、およびこれらの比LS阻
害率/R阻害率を求めた。 結果は第1表に示すとおりであつた。なお、第
1表のデータは全て12個体の平均の長さより、
LSとRを求めた。 表中、実験No.3〜5および7が本発明、他は比
較例である。
The present invention relates to a plant growth inhibitor, and in particular, it is an object of the present invention to provide a growth inhibitor that has a special physiological activity that hardly inhibits the growth of plant roots and only inhibits the growth of leaves and stems. Many compounds, including herbicides, have been known as plant growth inhibitors, but most of them inhibit the growth of both the roots and leaves and stems of plants, or inhibit the growth of the roots first. It inhibits growth and causes death. However, depending on the purpose, there is a demand for a plant growth inhibitor that suppresses only the growth of leaves and stems, but does not inhibit the growth of roots. For example, preventing lodging of rice plants, growing healthy seedlings, turf for golf courses and gardens, etc.
Regarding weeds near railway sleepers, it is desirable that the roots grow healthy and firmly, while the leaves and stems do not grow too tall (do not grow very much). Until now, no good so-called growth inhibitors have been known that can meet these purposes, and for this reason, we have developed an economical, non-toxic and safe product that is highly effective when used in relatively small amounts. The development of highly effective growth inhibitors is desired. While researching the extracts of Japanese parsley and parsley, the present inventors discovered a substance that suppresses the growth of leaves and stems without inhibiting the growth of the roots of rice seedlings.After extensive investigation into the surrounding area, they found that allyls in the aromatic ring Group (-CH 2 CH=
CH 2 ) or isoallyl group (-CH=CHCH 3 , methylenedioxy group (-OCH 2 O-), and methoxy group (-OCH 3 ) are bonded to aromatic compounds that have the above-mentioned special physiological activity on plants. The present invention was completed by confirming that 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene (common name: apiol)
Dimethoxy-3,4-methylenedioxybenzene (isoapiol), 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene (zylapiol) or 1-allyl-3-
The present invention provides a plant growth inhibitor containing methoxy-4,5-methylenedioxybenzene (myristicin) as an active ingredient. The above-mentioned compounds related to the present invention have the advantage of being easily procured, exhibiting the above-mentioned special physiological activity significantly in minute amounts, and being a constituent of essential oils of edible plants, and being extremely safe. . The above compounds related to the present invention are specifically shown below. Apiol and its isomers (alkenyldimethoxymethylenedioxybenzenes: Apior Isoapiol Zilapiol myristicin (allylmethoxymethylenedioxybenzenes): Myristicin In the present invention, it is necessary that the compound has an allyl group or an isoallyl group, a methylenedioxy group, and a methoxy group, and a compound lacking any one group does not have the special physiological activity targeted by the present invention. I can't perform to my full potential. For example, 2,3,4,5-tetramethoxyallylbenzene, anethole, and eigenol each have an allyl group, and heliotropin has a methylenedioxy group, but these have both groups in one molecule. Since it is not a natural substance, it does not have such physiological activity and has a greater effect of inhibiting root growth. Cinnamic acid also has no effect. According to the present invention, by applying a trace amount of the above-mentioned compound to plants, it is possible to obtain the effect of suppressing the growth of leaves and stems with almost no inhibition of root growth, thereby preventing lodging of rice and fostering healthy seedlings. In addition to being effective for
Since it suppresses the growth of grass leaves, the number of lawn mowings can be significantly reduced. Furthermore, weeds on the banks that support railroad sleepers are expected to have the effect of reinforcing the banks by spreading their roots, but if the leaves of these weeds grow too long, not only will they have to be cut, but from late summer onwards. Since fire hazards occur in the fall, it is extremely beneficial to keep the roots of these weeds healthy and to suppress only the growth of the leaves and stems. However, such objectives are not achieved using conventional herbicides. To carry out the present invention, the above compound may be dissolved or dispersed in water and sprayed onto target plants at a concentration of usually about 10 to 100 ppm. In addition,
It may be diluted with a solvent or used in combination with an emulsifier, etc.
Further, the compound may be formulated and used so as to be released gradually. Next, the present invention will be explained by examples. Example 1 A tube bottle with an inner diameter of 27 mm and a length of 118 mm is filled with 1.5 g of cellulose powder at the bottom, and an aqueous liquid containing the aromatic compounds shown in Table 1 dissolved or uniformly dispersed in water at a predetermined concentration is added to the bottle. A test bed was prepared by adding 6 ml of . Next, six 1 mm germinated paddy rice (variety: Tanginbozu) seeds prepared in advance under the same conditions were placed in each of these tube bottles, and then irradiated with 3000 lux and kept at 30°C for 12 days. Ta. After this, the effect of the compound on the growth of the seedlings was investigated by measuring the second leaf sheath (LS) and longest root length (R) of each seedling. In addition, 6 ml of water without any compounds was added and grown under the same conditions, and the second leaf sheath (LS) and longest root length (R) of the seedlings were measured.
were determined, and the respective growth inhibition rates [LS inhibition rate, R inhibition rate] and their ratio LS inhibition rate/R inhibition rate were determined. The results were as shown in Table 1. In addition, all the data in Table 1 are based on the average length of 12 individuals,
I found LS and R. In the table, Experiment Nos. 3 to 5 and 7 are of the present invention, and the others are comparative examples.

【表】 実施例 2 他方、比較例として第2表に示す各化合物につ
いて前記実施例と同様に実験したところ、第2表
に示すとおりの結果が得られた。
[Table] Example 2 On the other hand, as a comparative example, the compounds shown in Table 2 were tested in the same manner as in the above example, and the results shown in Table 2 were obtained.

【表】 以上の結果からわかるように、前記本発明では
明らかに根よりも葉鞘の生育抑制が大きいという
特殊な生理活性効果が認められたのに対し、比較
例としての本実施例ではアリル基のみ(実験No.
1、2および3)、もしくはメチレンジオキシ基
のみ(実験No.4)、および桂皮酸のような化合物
は根の生育阻害の方がはるかに大きいという結果
であつた。 実施例 3 10mgのアピオールをエチルアルコール10mlにと
かし、これを1の水に希釈して10ppmのアピオ
ール水溶液をつくつた。つぎに25℃のビニルハウ
ス中に草丈(長さ)5cm、最長の根の長さ14cmの
芝園1m2に対し上記アピオール水溶液を均一に散
布した。一方比較のために同条件(草丈、温度
等)の芝園1m2に水のみ1散布し、30日間経過
後草丈(長さ)、最長の根の長さを測つたところ、
結果は下記に示すとおりであつた。 草丈(長さ)
最長の根の長さ アピオール施用園 9.2cm
42cm 無施用園 15.3cm
46cm 上記結果からアピオールは芝の生育に対し特殊
な生理活性を有し、根の生育の阻害はほとんどな
く、草丈の生育を大幅に抑制することがわかつ
た。
[Table] As can be seen from the above results, in the present invention, a special physiologically active effect was clearly observed in that the growth inhibition of leaf sheaths was greater than that of roots, whereas in this example as a comparative example, allyl group Only (Experiment No.
1, 2, and 3), methylenedioxy group alone (Experiment No. 4), and compounds such as cinnamic acid had a much greater inhibition of root growth. Example 3 10 mg of Apiol was dissolved in 10 ml of ethyl alcohol, and this was diluted with 1 part water to prepare a 10 ppm Apiol aqueous solution. Next, the above Apiol aqueous solution was uniformly sprayed on 1 m 2 of a lawn with a plant height (length) of 5 cm and a longest root length of 14 cm in a vinyl greenhouse at 25°C. On the other hand, for comparison, we sprayed water alone on a 1 m 2 lawn under the same conditions (plant height, temperature, etc.) and measured the plant height (length) and longest root length after 30 days.
The results were as shown below. Plant height (length)
Longest root length Apiol application garden 9.2cm
42cm Unused garden 15.3cm
46cm From the above results, it was found that Apiol has special physiological activity on grass growth, hardly inhibits root growth, and significantly suppresses plant height growth.

Claims (1)

【特許請求の範囲】[Claims] 1 1−アリル−2,5−ジメトキシ−3,4−
メチレンジオキシベンゼン、1−プロペニル−
2,5−ジメトキシ−3,4−メチレンジオキシ
ベンゼン、1−アリル−2,3−ジメトキシ−
4,5−メチレンジオキシベンゼンまたは1−ア
リル−3−メトキシ−4,5−メチレンジオキシ
ベンゼンを有効成分とする植物の生育抑制剤。
1 1-allyl-2,5-dimethoxy-3,4-
Methylenedioxybenzene, 1-propenyl-
2,5-dimethoxy-3,4-methylenedioxybenzene, 1-allyl-2,3-dimethoxy-
A plant growth inhibitor containing 4,5-methylenedioxybenzene or 1-allyl-3-methoxy-4,5-methylenedioxybenzene as an active ingredient.
JP2824884A 1984-02-17 1984-02-17 plant growth inhibitor Granted JPS60172903A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2824884A JPS60172903A (en) 1984-02-17 1984-02-17 plant growth inhibitor

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2824884A JPS60172903A (en) 1984-02-17 1984-02-17 plant growth inhibitor

Publications (2)

Publication Number Publication Date
JPS60172903A JPS60172903A (en) 1985-09-06
JPH0533201B2 true JPH0533201B2 (en) 1993-05-19

Family

ID=12243274

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2824884A Granted JPS60172903A (en) 1984-02-17 1984-02-17 plant growth inhibitor

Country Status (1)

Country Link
JP (1) JPS60172903A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60224604A (en) * 1984-04-24 1985-11-09 Shin Etsu Chem Co Ltd Plant growth inhibitor and method of inhibition of growth
WO1998033385A1 (en) * 1997-01-31 1998-08-06 Monsanto Company Process and compositions for enhancing reliability of exogenous chemical substances applied to plants
WO2019175712A1 (en) * 2018-03-14 2019-09-19 Basf Corporation New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE786067A (en) * 1971-07-10 1973-01-10 Bayer Ag COMPOSITION INTENDED FOR THE REGULATION OF PLANT GROWTH

Also Published As

Publication number Publication date
JPS60172903A (en) 1985-09-06

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