JPS638304A - Flowering promoter - Google Patents

Flowering promoter

Info

Publication number
JPS638304A
JPS638304A JP15360886A JP15360886A JPS638304A JP S638304 A JPS638304 A JP S638304A JP 15360886 A JP15360886 A JP 15360886A JP 15360886 A JP15360886 A JP 15360886A JP S638304 A JPS638304 A JP S638304A
Authority
JP
Japan
Prior art keywords
formula
expressed
flowering
active ingredient
plants
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
JP15360886A
Other languages
Japanese (ja)
Inventor
Yoshi Iwamura
岩村 俶
Toshiaki Kametani
亀谷 寿昭
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.)
Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry Co Ltd
Original Assignee
Ihara Chemical Industry Co Ltd
Kumiai Chemical Industry 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 Ihara Chemical Industry Co Ltd, Kumiai Chemical Industry Co Ltd filed Critical Ihara Chemical Industry Co Ltd
Priority to JP15360886A priority Critical patent/JPS638304A/en
Publication of JPS638304A publication Critical patent/JPS638304A/en
Pending legal-status Critical Current

Links

Landscapes

  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

PURPOSE:A flowering promoter, containing 2-chloro-4-cyclohexylamino-6- ethylamino-1,3,5-triazine as an active ingredient, capable of exhibiting improved effect on increase and promotion of flowering of plants and useful for plants, e.g. asparagus, etc. CONSTITUTION:A flowering promoter containing 2-chloro-4-cyclohexylamino-6- ethylamino-1,3,5-triazine expressed by formula I as an active ingredient. The compound expressed by formula I is obtained by reacting cyanuric chloride expressed by formula II with cyclohexylamine expressed by formula III in a solvent in the presence of a base at <=0 deg.C-about 10 deg.C and reacting the resultant compound expressed by formula IV with ethylamine in a solvent in the presence of a base at room temperature - 80 deg.C. The compound expressed by formula I can be directly used or a carrier or adjuvant can be added and formulated into wettable powder, emulsion, dust, etc., to treat seeds or other parts. The application amount is 0.1-3,000ppm active ingredient concentration.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は2−クロロ−生−シクロへキシルアミノ−6−
ニチルアミノーL3t5−)リアジン(以下本発明化合
物という)を有効成分として含有すること暑特徴とする
植物の開花の増加及び促進をする薬剤に関するものであ
ろ0(従来の技術) 食用作物の1つであるアスパラガスは、通常雄株の方が
雌株に比べ収量が3割程度高(、また雄株はビタミン含
量が高く、芽の形が良いなど食用に適しており、農業生
産上有益とされている。従来、アスパラガスの生長を促
進させるために植物生長調節剤としてベンジルアデニン
・ナフチル酢酸、アプシジン酸、ジベンリンを配合する
ことが行われているが、アス・ぞラガスの開花を促進さ
せる効果を有する薬剤については知らねていない。また
、アトラジン等1−ラフジン誘導体が除草剤として有効
なことが仰られているが(特公昭35−9799号公報
)、開花促進作用は示さない。
DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention provides 2-chloro-raw-cyclohexylamino-6-
Contains nitylamino-L3t5-) riazine (hereinafter referred to as the compound of the present invention) as an active ingredient and relates to a drug that increases and promotes flowering of plants characterized by heat (prior art) It is one of the edible crops. Male asparagus plants usually have a yield that is about 30% higher than female plants (also, male plants have higher vitamin content and better-shaped buds, making them suitable for eating and are considered beneficial for agricultural production. Conventionally, benzyladenine/naphthyl acetic acid, apsidic acid, and dibenline have been added as plant growth regulators to promote the growth of asparagus; There is no knowledge of the drugs that have this effect.Furthermore, 1-lafuzine derivatives such as atrazine are said to be effective as herbicides (Japanese Patent Publication No. 35-9799), but they do not exhibit a flowering-promoting effect.

(発明が解決しようとする問題点) アスパラガスの開花期は播種後2〜3年である。従って
上記の雄株選抜のための雌雄判定?その時期まで待たな
ければならなかった。≠ヰ←開花促進作用により、幼植
物段階で雄株を(選抜し・雄株のみを畑に定植すること
ができれば、アスパラガスの増産ないしは増収に結びつ
くものであり、そのような技術の開発が待望されていた
(Problems to be Solved by the Invention) The flowering period of asparagus is 2 to 3 years after sowing. Therefore, is it sex determination for male plant selection mentioned above? I had to wait until that time. ≠ヰ← If it were possible to select male plants at the seedling stage and plant only the male plants in the field due to their flowering promotion effect, it would lead to increased production or yield of asparagus, and the development of such technology is It was long awaited.

本発明省らは、従来典型的な光合成阻害型の土壌処理剤
として知られている、トリアジン誘導体について鋭意研
究した結果、本発明化合物をアスパラガスの種子に処理
したところ、播種後25日〜30日という短期間で高い
花芽形成率に示して雌雄判定が可能となり、更に本体を
枯死させろこともないことを見出し、本発明化合物させ
るに至った。
As a result of intensive research on triazine derivatives, which are conventionally known as typical photosynthesis-inhibiting soil treatment agents, the Ministry of the Invention and others found that asparagus seeds were treated with the compound of the present invention, and 25 to 30 days after sowing. It was discovered that the flower bud formation rate was high in a short period of one day, making it possible to determine the sex of the plant, and the plant did not cause the plant to wither and die, leading to the development of the compound of the present invention.

(問題点を解決するための手段) 本発明の開花促進剤は2−クコロー牛−シクロへキジル
アばノー6−ニチルアミノー1.3.5−トリアジンを
有効成分として含有してなる。
(Means for Solving the Problems) The flowering promoter of the present invention contains 2-Cucoro-cyclohexylamino-6-nitylamino-1.3.5-triazine as an active ingredient.

本発明化合物は次の反応式に従って製造することができ
る。
The compound of the present invention can be produced according to the following reaction formula.

(I) 塩化シアヌルを適当な溶媒に溶解するが懸濁させ、シク
ロヘキシルアミンおよび塩基を○℃以下〜10℃位で加
え反応させろり溶媒としてはアセトン−水、アセトン、
メチルエチルケトン、水、アセトニトリル、エーテル、
テトラヒドロフラン、ジオキサン、ジメチルホルムアミ
ド、ジメチルスルホキシド、ベンゼン、トルエン、キシ
レン等が使用出来るが、アセトン−水に懸濁させるのが
好ましい。塩基としては重炭酸ナトリウム、炭酸ナトリ
ウム、炭酸カリウム、水酸化ナトリウム、水酸化力IJ
ウム、トリエチルアミン等を使用する。反応は0℃以下
にて行う。
(I) Cyanuric chloride is dissolved or suspended in a suitable solvent, and cyclohexylamine and a base are added and reacted at a temperature of 10°C or less. Examples of solvents include acetone-water, acetone,
Methyl ethyl ketone, water, acetonitrile, ether,
Tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, benzene, toluene, xylene, etc. can be used, but suspension in acetone-water is preferable. Bases include sodium bicarbonate, sodium carbonate, potassium carbonate, sodium hydroxide, hydroxide IJ
um, triethylamine, etc. The reaction is carried out at 0°C or lower.

生成した沈殿を情裂もしくは精製することな(エチルア
ミンとの反応に供する。反応溶媒および塩基は前述した
ものを使用し対応する当量のエチルアミンおよび塩基を
室温にて加える。反応は室温乃至80℃にて行う。終了
後生成した沈澱を口実し再結晶又はカラムクロマトグラ
フィーにて精製を行い本発明で使用するトリアノン誘導
体を得ることができる。本発明の2−クロロ−4−シク
ロへキシルアミノ−6−ニチルアミノー1p 3y 5
  トリアジンは融点127〜130℃である。
The generated precipitate is not separated or purified (subject to reaction with ethylamine. The reaction solvent and base used are those mentioned above, and corresponding equivalent amounts of ethylamine and base are added at room temperature. The reaction is carried out at room temperature to 80°C. After completion, the trianone derivative used in the present invention can be obtained by recrystallization or purification by column chromatography using the precipitate formed.2-chloro-4-cyclohexylamino-6- of the present invention. Nithylamino 1p 3y 5
Triazine has a melting point of 127-130°C.

本発明化合物を開花促進剤として使用する場合、化合物
のみ、またはこれに農薬の製剤化に際し一般的に用いら
れる担体、界面活性剤、分散剤、補助剤等を配合して、
水和剤、乳剤または粉剤等の各種型態VC製剤して種子
又はその他の部所に処理することができる。
When the compound of the present invention is used as a flowering promoter, the compound alone or in combination with carriers, surfactants, dispersants, adjuvants, etc. commonly used in the formulation of agricultural chemicals,
Various types of VC preparations such as wettable powders, emulsions, or powders can be applied to seeds or other parts.

+31!I剤化に際して用いられる担体としては、例え
ば、4ルク、ベントナイト、クレー、カオリン、珪藻土
、ホワイトカーボン、バーミキュライト、消石灰、珪砂
、硫安、尿素等の固体担体、ジメチルスルホキシド、イ
ンプロピルアルコール、キシレン、シクロヘキサン、メ
チルナフタレン等の液体祁体等が挙げられる。界面活性
剤および分子V1.剤としては、例えば、アルコール硫
酸エステル塩、アルキルアリールスルホン酸塩、IJ 
クニンスルホン酸塩、ポリオキシエチレングリコールエ
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ンルビタンモノアルキレート等が
挙げられる。補助剤としては、汐11えば、カルボキン
メチルセルロース、ポリエチレングリコール、アラビア
ゴム等が挙げられる。製剤した薬剤の使用に際しては、
適当な濃度に希釈して浸漬するかまたは直接施用する。
+31! Examples of carriers used in forming the I-forming agent include solid carriers such as quartz, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, dimethyl sulfoxide, inpropyl alcohol, xylene, and cyclohexane. , methylnaphthalene, and the like. Surfactants and Molecules V1. Examples of the agent include alcohol sulfate ester salt, alkylaryl sulfonate, IJ
Examples include Kuninsulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, polyoxyethylene rubitan monoalkylate, and the like. Examples of the auxiliary agent include Shio 11, carboquine methylcellulose, polyethylene glycol, gum arabic, and the like. When using formulated drugs,
Dilute to appropriate concentration and soak or apply directly.

薬剤を施用する場合の有効成分の濃度は0.1〜300
0 ppmである。
When applying the drug, the concentration of the active ingredient is 0.1-300
0 ppm.

次に、本発明の開花促進剤の実施例を挙げるが、本発明
はこの範囲に限定されるものではない0なお、%は重量
百分率を示T0 実施例1 (水和剤) 化合物゛10%、エマルグン810(花王石鹸株式会社
登録商標)o、5%、デモールN(花王石鹸株式会社登
録商標)05%、クニライト201 (クニεネ工業株
式会社登録商標)20.0%およびジ−クライトaA(
ジ−クライト株式会社登録商ff1)69.0%?均一
に混合粉砕して水和剤とした○ 実施例2 (乳剤) 化合物 30%、シクロへキサノン20%、ポリオキシ
エチンンアルキルアリールエーテル11%、アルキルベ
ンゼンスルホン酸カルシウム4%およびメチルナフタレ
ン35%を均一に溶解して乳剤とした。
Next, Examples of the flowering promoter of the present invention will be given, but the present invention is not limited to this range. Note that % indicates weight percentage. , Emalgun 810 (registered trademark of Kao Soap Co., Ltd.) o, 5%, Demol N (registered trademark of Kao Soap Co., Ltd.) 05%, Kunilite 201 (registered trademark of Kuni Ene Industries Co., Ltd.) 20.0%, and Zikrite aA (
Sickle Co., Ltd. registered trader ff1) 69.0%? Uniformly mixed and ground to make a wettable powder Example 2 (Emulsion) Compound 30%, cyclohexanone 20%, polyoxyethyne alkylaryl ether 11%, calcium alkylbenzene sulfonate 4% and methylnaphthalene 35%. It was uniformly dissolved to form an emulsion.

(発明の効果) 次に本発明化合物の奏する効果を試験例をもって説明す
る。
(Effects of the Invention) Next, the effects of the compounds of the present invention will be explained using test examples.

試験例I IA)  試験方法 材料としてアスノぞラガス(樗晒砦亡IC鳳11sL、
)Mary Washington 50oWを用いた
0種子を所定濃度の薬剤溶液に浸漬し、25℃照射条件
下(インキュベータ、300ルツクス)で12日間薬剤
処理を行りた0処理後・培養土に移植し、日長12時間
、25℃の温室で育成した。花芽形成は播種後25日目
に測定した。1試験区は25ないし50個体とした◇尚
、薬剤溶液は、供試薬剤を005%のジメチルスルホキ
シドに溶解し、水で希釈して調整した。
Test example I
) 0 seeds using Mary Washington 50oW were immersed in a drug solution with a predetermined concentration, and treated with the drug for 12 days under 25°C irradiation conditions (incubator, 300 lux). After the 0 treatment, they were transplanted into culture soil and The cells were grown in a greenhouse at 25°C for 12 hours. Flower bud formation was measured 25 days after sowing. Each test plot had 25 to 50 individuals.◇The drug solution was prepared by dissolving the test drug in 0.05% dimethyl sulfoxide and diluting it with water.

(尋 試験結果 結果を第1表に示す 第1表 花芽は雄花、雌花ともに観察された。対照剤のアトラジ
ンは、播種後1力月目には半数が、2力月目にはすべて
の実生が枯死した。
(Test results are shown in Table 1) Flower buds on the first surface were observed in both male and female flowers.Atrazine, the control agent, affected half of the seedlings in the first month after sowing, and all the seedlings in the second month after sowing. has withered and died.

本発明化合物は、高い花芽形成率を示すとともに、高い
生存率が認められた。
The compound of the present invention showed a high flower bud formation rate and a high survival rate.

Claims (1)

【特許請求の範囲】[Claims] (1)2−クロロ−4−シクロヘキシルアミノ−6−エ
チルアミノ−1,3,5−トリアジンを有効成分として
含有する植物の開花促進剤
(1) Plant flowering promoter containing 2-chloro-4-cyclohexylamino-6-ethylamino-1,3,5-triazine as an active ingredient
JP15360886A 1986-06-30 1986-06-30 Flowering promoter Pending JPS638304A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15360886A JPS638304A (en) 1986-06-30 1986-06-30 Flowering promoter

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15360886A JPS638304A (en) 1986-06-30 1986-06-30 Flowering promoter

Publications (1)

Publication Number Publication Date
JPS638304A true JPS638304A (en) 1988-01-14

Family

ID=15566204

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15360886A Pending JPS638304A (en) 1986-06-30 1986-06-30 Flowering promoter

Country Status (1)

Country Link
JP (1) JPS638304A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01208553A (en) * 1988-11-29 1989-08-22 Honda Motor Co Ltd Piston for internal combustion engine
US10342570B2 (en) 2014-02-03 2019-07-09 Medinol Ltd. Device for traversing vessel occlusions and method of use
US10426923B2 (en) 2014-02-03 2019-10-01 Medinol Ltd. Catheter tip assembled with a spring
US10850065B2 (en) 2010-02-09 2020-12-01 Medinol Ltd. Catheter tip assembled with a spring

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01208553A (en) * 1988-11-29 1989-08-22 Honda Motor Co Ltd Piston for internal combustion engine
US10850065B2 (en) 2010-02-09 2020-12-01 Medinol Ltd. Catheter tip assembled with a spring
US10342570B2 (en) 2014-02-03 2019-07-09 Medinol Ltd. Device for traversing vessel occlusions and method of use
US10426923B2 (en) 2014-02-03 2019-10-01 Medinol Ltd. Catheter tip assembled with a spring

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