JP2881443B2 - Novel oxyalkylated quaternary ammonium compound, production method thereof and plant growth regulator containing the same as active ingredient - Google Patents
Novel oxyalkylated quaternary ammonium compound, production method thereof and plant growth regulator containing the same as active ingredientInfo
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- JP2881443B2 JP2881443B2 JP30147588A JP30147588A JP2881443B2 JP 2881443 B2 JP2881443 B2 JP 2881443B2 JP 30147588 A JP30147588 A JP 30147588A JP 30147588 A JP30147588 A JP 30147588A JP 2881443 B2 JP2881443 B2 JP 2881443B2
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Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、新規なオキシアルキル化第４アンモニウム
化合物、その製造方法及びその化合物を有効成分とする
植物成長調節剤に関する。Description: TECHNICAL FIELD The present invention relates to a novel oxyalkylated quaternary ammonium compound, a method for producing the same, and a plant growth regulator containing the compound as an active ingredient.
［従来の技術］ 植物の生育に関係する薬剤としては各種のものが知ら
れているが、従来の薬剤は、薬害が出やすいものや、限
定された植物にしか効果がないものが多かった。[Prior Art] Various agents are known as agents related to the growth of plants, but many of the conventional agents are susceptible to phytotoxicity or are effective only on limited plants.
従って、薬害が少なく、かつ多種類の植物に有効な植
物成長調節剤が求められていた。Therefore, a plant growth regulator which is less phytotoxic and is effective for many kinds of plants has been demanded.
［発明が解決しようとする課題］ 本発明の目的は、薬害が少なく、かつ多種類の植物に
有効な植物成長調節機能を有する新規オキシアルキル化
第４アンモニウム化合物、その製造方法及びその化合物
を有効成分とする植物成長調節剤を提供する処にある。[Problems to be Solved by the Invention] An object of the present invention is to provide a novel oxyalkylated quaternary ammonium compound having a low plant injury and having a plant growth regulating function effective for many kinds of plants, a method for producing the same, and a method for producing the compound. The present invention is to provide a plant growth regulator as a component.
［課題を解決するための手段］ 本発明の新規オキシアルキル化第４アンモニウム化合
物は、一般式 ［式中、R1は炭素数６〜22のアルキル基又はアルケニル
基、R2は炭素数１〜４のアルキル基又はヒドロキシアル
キル基を表わす。R3及びR4は（BO）xHであり、ここで、
Ｂは炭素数１〜４のアルキレン基、ｘは１〜５の整数ま
たは非整数を表わす。[Means for Solving the Problems] The novel oxyalkylated quaternary ammonium compound of the present invention has the general formula [Wherein, R 1 represents an alkyl group or alkenyl group having 6 to 22 carbon atoms, and R 2 represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. R 3 and R 4 are (BO) x H, where:
B represents an alkylene group having 1 to 4 carbon atoms, and x represents an integer of 1 to 5 or a non-integer.
Ａ はR5NHR6COO 、 R5CH（NH2）COO 又は であり、ここで、R5はＨ、炭素数１〜４のアルキル基、
CH2（OH）−、CH3SCH2CH2−、 NH2CH2（CH2）3−もしくはHSCH2−を表わし、R6はCH2又
はベンゼン核を表わす。］ で示されるオキシアルキル化第４アンモニウム化合物で
ある。A Is RFiveNHR6COO , RFiveCH (NHTwo) COO OrAnd where RFiveIs H, an alkyl group having 1 to 4 carbon atoms,
CHTwo(OH)-, CHThreeSCHTwoCHTwo−, NHTwoCHTwo(CHTwo)Three-Or HSCHTwo−, R6Is CHTwoor
Represents a benzene nucleus. An oxyalkylated quaternary ammonium compound represented by the formula:
is there.
本発明化合物の製造方法は、一般式、 ［式中、R1は炭素数６〜22のアルキル基又はアルケニル
基R2炭素数１〜４のアルキル基又はヒドロキシアルキル
基を表わす。R3及びR4は（BO）xHであり、ここで、Ｂは
炭素数１〜４のアルキレン基、ｘは１〜５の整数または
非整数を表わす。ＹはCl、Br、Ｉ又はＦを表わす。］ で示される第４アンモニウム化合物と、 一般式 R5NHR6COOD……（３）で示される化合物、 一般式 で示される化合物、一般式 で示される化合物、一般式 R5CH（NH2）COOD……（６）で示される化合物、及び一
般式 で示される化合物 ［式中、R5はＨ、炭素数１〜４のアルキル基、 CH2（OH）−、CH3SCH2CH2−、 NH2CH2（CH2）3−若しくはHSCH2−を表わし、R6はCH2又
はベンゼン核を表わす。Ｄはアルカリ金属原子若しくは
アルカリ土類金属原子を表わす。］ からなる群から選ばれた少なくとも１種を、 炭素数１〜６の直鎖または分岐アルコール、メチルエ
チルケトン、ジメチルスルホキサイド、ジメチルホスム
アミド、ジオキサン、酢酸エチル、及びシクロヘキサノ
ールからなる群より選ばれた少なくとも１種の溶媒中
で、 上記の一般式（１）で示される新規オキシアルキル化
第４アンモニウム化合物の少量の存在下又は不存在下で
反応させることを特徴とするものである。The method for producing the compound of the present invention has the general formula: [In the formula, R 1 represents an alkyl group or alkenyl group having 6 to 22 carbon atoms, and R 2 represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. R 3 and R 4 are (BO) x H, wherein B represents an alkylene group having 1 to 4 carbon atoms, and x represents an integer of 1 to 5 or a non-integer. Y represents Cl, Br, I or F. A quaternary ammonium compound represented by the following formula: and a compound represented by the general formula R 5 NHR 6 COOD. A compound represented by the general formula A compound represented by the general formula R 5 CH (NH 2 ) COOD ... (6), and a compound represented by the general formula: Wherein R 5 is H, an alkyl group having 1 to 4 carbon atoms, CH 2 (OH) —, CH 3 SCH 2 CH 2 —, NH 2 CH 2 (CH 2 ) 3 — or HSCH 2 —, and R 6 represents CH 2 or a benzene nucleus. D represents an alkali metal atom or an alkaline earth metal atom. At least one selected from the group consisting of: a linear or branched alcohol having 1 to 6 carbon atoms, methyl ethyl ketone, dimethyl sulfoxide, dimethyl fosamide, dioxane, ethyl acetate, and cyclohexanol. The reaction is carried out in at least one of the above-mentioned solvents in the presence or absence of a small amount of the novel oxyalkylated quaternary ammonium compound represented by the general formula (1).
本発明の化合物は、薬害が少なく、しかも多種類の植
物に有効な植物成長調節機能を有するものである。The compound of the present invention has less phytotoxicity and has a plant growth regulating function that is effective for many kinds of plants.
本発明の化合物の製造方法における反応条件は、反応
溶媒の種類によっても異なるが、一般的に次のようなも
のである。すなわち、30℃〜100℃の温度で３〜24時間
撹拌反応した後、生成するアルカリ金属ハライドもしく
はアルカリ土類金属ハライドを濾過により除去し、その
濾液を濃縮することにより、一般式（１）で示される化
合物を得ることができる。The reaction conditions in the method for producing the compound of the present invention vary depending on the type of the reaction solvent, but are generally as follows. That is, after reacting with stirring at a temperature of 30 ° C. to 100 ° C. for 3 to 24 hours, the generated alkali metal halide or alkaline earth metal halide is removed by filtration, and the filtrate is concentrated to obtain the compound represented by the general formula (1). The compounds shown can be obtained.
さらに、この濃縮物をアセトン、メチルエチルケト
ン、トルエン、ベンゼン、キシレン等に溶解して濾過し
た後、濾液を濃縮することにより精製出来る。Further, the concentrate can be purified by dissolving the concentrate in acetone, methyl ethyl ketone, toluene, benzene, xylene, or the like, filtering, and then concentrating the filtrate.
なお、本発明の反応の際、反応生成物の10wt.％以下
の量の一般式（１）の化合物を添加して反応を行なうこ
とも可能である。In the reaction of the present invention, the reaction can be carried out by adding the compound of the general formula (1) in an amount of 10% by weight or less of the reaction product.
本発明の製造方法において使用する一般式（２）で示
される化合物としては、例えば、オクチルメチルジヒド
ロキシエチルアンモニウムクロライド ラウリルメチルジヒドロキシエチルアンモニウムブロマ
イド オレイルエチルジヒドロキシエチルアンモニウムアイオ
ダイド ステアリルメチルジヒドロキシプロピルアンモニウムク
ロライド ヘキシルエチルジヒドロキシブチルアンモニウムブロマ
イド オレイルトリヒドロキシエチルアンモニウムクロライド ラウリルトリヒドロキシエチルアンモニウムクロライド オレイルメチルジヒドロキシエトキシエチルアンモニウ
ムクロライド 等が挙げられる。Examples of the compound represented by the general formula (2) used in the production method of the present invention include, for example, octylmethyldihydroxyethylammonium chloride Lauryl methyl dihydroxyethyl ammonium bromide Oleylethyldihydroxyethylammonium iodide Stearyl methyl dihydroxypropyl ammonium chloride Hexylethyldihydroxybutylammonium bromide Oleyl trihydroxyethyl ammonium chloride Lauryl trihydroxyethyl ammonium chloride Oleylmethyldihydroxyethoxyethylammonium chloride And the like.
また、一般式（３）、（４）、（５）、（６）又は
（７）で示される化合物としては、例えば、 等の、アミノ酸のアルカリ金属又はアルカリ土類 金属
塩が挙げられる。Further, as the compound represented by the general formula (3), (4), (5), (6) or (7), for example, And alkali metal or alkaline earth metal salts of amino acids.
本発明の製造方法において使用する一般式（２）の化
合物と一般式（３）、（４）、（５）、（６）又は
（７）の化合物の量的な関係は、一般式（２）の化合物
１モルに対して、一般式（３）、（４）、（５）、
（６）又は（７）の化合物１〜1.5モルが好ましい。ま
た、反応の際に、一般式（２）の化合物と一般式
（３）、（４）、（５）、（６）又は（７）の化合物の
合計量に対して10wt.％以下の水分が存在していても、
なんら差しつかえない。The quantitative relationship between the compound of the general formula (2) and the compound of the general formula (3), (4), (5), (6) or (7) used in the production method of the present invention is represented by the general formula (2) ) With respect to 1 mol of the compound of formula (3), (4), (5),
The compound of (6) or (7) is preferably 1 to 1.5 mol. In addition, at the time of the reaction, a water content of 10 wt.% Or less based on the total amount of the compound of the general formula (2) and the compound of the general formula (3), (4), (5), (6) or (7). Is present,
No problem.
本発明における反応の一例を式で示すと次のようにな
る。An example of the reaction in the present invention is represented by the following formula.
本発明の製造方法に使用する溶媒は、一般式（２）の
化合物、あるいは一般式（３）〜（７）の化合物の両方
又は何れか一方を溶解するものであればよい。そのよう
な溶媒としては、炭素数１〜６の直鎖もしくは分岐アル
コール、酢酸エチル、ジオキサン、メチルエチルケト
ン、シクロヘキサノール、ジメチルスルホキサイド、ジ
メチルホスムアミド等が挙げられる。溶媒の使用量とし
ては、一般式（２）の化合物並びに一般式（３）、
（４）、（５）、（６）若しくは（７）の化合物の合計
量の等量ないし10倍量が適当である。 The solvent used in the production method of the present invention may be any solvent that dissolves the compound of the general formula (2) and / or the compounds of the general formulas (3) to (7). Examples of such a solvent include linear or branched alcohols having 1 to 6 carbon atoms, ethyl acetate, dioxane, methyl ethyl ketone, cyclohexanol, dimethyl sulfoxide, dimethyl fosamide and the like. As the amount of the solvent used, the compound of the general formula (2) and the general formula (3)
An equivalent to 10 times the total amount of the compounds (4), (5), (6) or (7) is appropriate.
前記したように、本発明の反応を達成させるには、３
〜24時間の反応時間で充分である。反応終了後、反応系
から溶媒に溶解している反応生成物（本発明の化合物）
を濾別することにより、副生したアルカリ金属ハライド
もしくはアルカリ土類金属ハライドより分離する。濾液
から溶媒を除去することにより、本発明の化合物を得る
ことができる。As mentioned above, to achieve the reaction of the present invention, 3
A reaction time of 2424 hours is sufficient. After completion of the reaction, the reaction product dissolved in the solvent from the reaction system (the compound of the present invention)
Is separated from the alkali metal halide or alkaline earth metal halide by-produced. The compound of the present invention can be obtained by removing the solvent from the filtrate.
さらに精製を必要とする場合は、上記の溶媒を除去し
た濃縮物を炭素数１〜６の直鎖または分岐アルコール、
アセトン、ベンゼン、トルエン、キシレン等に溶解した
後、濾別し、濾液を濃縮するか、又は、濾液を冷却して
結晶として析出させればよい。If further purification is required, the concentrate from which the above-mentioned solvent has been removed is subjected to a straight-chain or branched alcohol having 1 to 6 carbon atoms,
After dissolving in acetone, benzene, toluene, xylene or the like, the solution may be separated by filtration and the filtrate may be concentrated, or the filtrate may be cooled to precipitate as crystals.
なお、反応系内に、相当する一般式（１）の化合物
を、一般式（２）の化合物並びに一般式（３）、
（４）、（５）、（６）若しくは（７）の化合物の合計
量の10wt.％以下の量だけ添加する場合、又は、一般式
（２）の化合物としてクロライド又はブロマイドを使用
する場合には、一般式（２）の化合物の10wt.％以下の
沃化アルカリを添加してもよい。また、反応時における
着色防止のため、少量の窒素ガスを通入してもよい。In the reaction system, the corresponding compound of the general formula (1) is replaced with a compound of the general formula (2) and a compound of the general formula (3).
(4) When adding only 10% by weight or less of the total amount of the compound of (5), (6) or (7), or when using chloride or bromide as the compound of the general formula (2) May be added with 10% by weight or less of an alkali iodide of the compound of the general formula (2). Further, a small amount of nitrogen gas may be introduced to prevent coloring during the reaction.
［実施例］ 次に、本発明を実施例により具体的に説明する。[Examples] Next, the present invention will be specifically described with reference to Examples.
実施例１ オレイルメチルジヒドロキシエチルアンモニウムクロ
ライド40.5g、グリシンカリウム塩13g、イソブタノール
200gを、撹拌機・冷却コンデンサー付四ツ口フラスコに
入れ、少量の窒素ガスを通入しつつ、40〜50℃で６時間
反応させた。反応終了後、生成した沈澱物を濾別し、さ
らに沈澱物を30mlのイソブタノールで洗浄した後、濾液
及び洗液を減圧濃縮した。この濃縮物をトルエン200gに
溶解した後濾別し、濾液を濃縮してワックス状のオレイ
ルメチルジヒドロキシエチルアンモニウムグリシン（次
式Ｉ）43.1g（理論量4 4.4g）を得た。Example 1 Oleylmethyldihydroxyethylammonium chloride 40.5 g, glycine potassium salt 13 g, isobutanol
200 g was placed in a four-necked flask equipped with a stirrer / cooling condenser and allowed to react at 40 to 50 ° C. for 6 hours while passing a small amount of nitrogen gas. After the reaction was completed, the formed precipitate was separated by filtration, and the precipitate was washed with 30 ml of isobutanol, and the filtrate and the washing were concentrated under reduced pressure. This concentrate was dissolved in 200 g of toluene and then filtered off. The filtrate was concentrated to obtain 43.1 g (theoretical amount 44.4 g) of oleylmethyldihydroxyethylammonium glycine (the following formula I) in the form of wax.
元素分析および赤外吸収スペクトル分析を行なった結果
を以下に示す。 The results of elemental analysis and infrared absorption spectrum analysis are shown below.
元素分析値（％） C 67.05（67.56） H 11.75（11.71） O 14.18（14.41） N 6.21（ 6.30） C 0.01 （ ）内計算値 赤外吸収スペクトル分析 オレイルメチルジヒドロキシエチルアンモニウムに帰
因する吸収の他、グリシンに帰因する−COO の吸収を1
600cm-1、1380cm-1に認めた。Elemental analysis value (%) C 67.05 (67.56) H 11.75 (11.71) O 14.18 (14.41) N 6.21 (6.30) C 0.01 Calculated value in parentheses Infrared absorption spectrum analysis Attributable to oleylmethyldihydroxyethylammonium
-COO due to glycine Absorption of 1
600cm-1, 1380cm-1Admitted.
実施例２ ラウリルメチルジヒドロキシエチルアンモニウムブロ
マイド37.8g、バリンナトリウム塩13.9g、ラウリルメチ
ルジヒドロキシエチルアンモニウムバリン3g、イソプロ
パノール200gを、撹拌機・冷却コンデンサー付四ツ口フ
ラスコに入れ、少量の窒素ガスを通入しつつ、50℃で４
時間反応させた。反応終了後、生成した沈澱物を濾別
し、さらに沈澱物を30mlのイソプロパノールで洗浄した
後、濾液及び洗液を減圧濃縮してイソプロパノールを留
去した。この濃縮物をベンゼン200gに溶解したのち不溶
物を濾別し、濾液からベンゼンを留去してワックス状の
ラウリルメチルジヒドロキシエチルアンモニウムバリン
（次式II）39.3g（理論量41.4g）を得た。Example 2 37.8 g of laurylmethyldihydroxyethylammonium bromide, 13.9 g of valine sodium salt, 3 g of laurylmethyldihydroxyethylammonium valine, and 200 g of isopropanol were put into a four-necked flask equipped with a stirrer / cooling condenser, and a small amount of nitrogen gas was introduced. 4 at 50 ° C
Allowed to react for hours. After completion of the reaction, the resulting precipitate was separated by filtration, and the precipitate was washed with 30 ml of isopropanol. The filtrate and the washing were concentrated under reduced pressure to remove isopropanol. After dissolving this concentrate in 200 g of benzene, the insoluble matter was filtered off, and benzene was distilled off from the filtrate to obtain 39.3 g (theoretical amount 41.4 g) of waxy laurylmethyldihydroxyethylammonium valine (formula II). .
元素分析値（％） C 63.58（63.76） H 11.53（11.59） O 15.40（15.45） N 6.71（ 6.76） Br 0.02 （ ）内計算値 実施例３ デシルトリヒドロキシエチルアンモニウムクロライド
32.5g、イソプロパノール200g、トリプトファンカリウ
ム塩25.6g、沃化カリウム3gを、撹拌機・冷却コンデン
サー付四ツ口フラスコに入れ、60℃にて８時間反応させ
た。１夜間放置後、沈澱物を濾別し、さらに沈澱物をイ
ソプロパノール200gで洗浄した後、濾液及び洗浄を濃縮
した。この濃縮物をトルエン200gに溶解したのち沈澱物
を濾別し、濾液を濃縮してワックス状のデシルトリヒド
ロキシエチルアンモニウムトリプトファン（次式III）4
5.6g（理論量48.1g）を得た。 Elemental analysis (%) C 63.58 (63.76) H 11.53 (11.59) O 15.40 (15.45) N 6.71 (6.76) Br 0.02 Calculated in parentheses Example 3 Decyl trihydroxyethyl ammonium chloride
32.5 g, isopropanol 200 g, tryptophan potassium salt 25.6 g, and potassium iodide 3 g were put into a four-necked flask equipped with a stirrer / cooling condenser and reacted at 60 ° C. for 8 hours. After standing overnight, the precipitate was filtered off, and the precipitate was washed with 200 g of isopropanol. The filtrate and the wash were concentrated. After dissolving this concentrate in 200 g of toluene, the precipitate is separated by filtration, and the filtrate is concentrated to give waxy decyltrihydroxyethylammonium tryptophan (formula III) 4
5.6 g (48.1 g of theory) were obtained.
元素分析値（％） C 63.98（64.86） H 9.79（ 9.77） N 8.68（ 8.73） O 16.51（16.63） C 0.02 （ ）内計算値 実施例４ 実施例１で得られた化合物の0.0001％、0.001％、0.0
1％、0.1％の各水溶液を作り、大豆、トウモロコシ、稲
（水稲）の種子を、25℃で12時間これらの水溶液に浸漬
した。次いで、ポリエチレンカップにバーミキュライト
を入れ上記種子を播種した。これを25℃に保ったグリー
ンハウス内に置き、10日間毎日冠水生育した。同時に、
水に上記種子を浸漬したものを比較例（無処理）とし
た。 Elemental analysis value (%) C 63.98 (64.86) H 9.79 (9.77) N 8.68 (8.73) O 16.51 (16.63) C 0.02 Calculated value in parentheses Example 4 0.0001%, 0.001% of the compound obtained in Example 1 , 0.0
1% and 0.1% aqueous solutions were prepared, and soybean, corn, and rice (rice) seeds were immersed in these aqueous solutions at 25 ° C. for 12 hours. Next, vermiculite was placed in a polyethylene cup, and the above seeds were sown. This was placed in a green house maintained at 25 ° C., and was flooded every day for 10 days. at the same time,
What immersed the said seed in water was set as the comparative example (untreated).
茎葉の長さ、茎葉の枚数及び根の長さを測定した結果
を表１〜３に示す。表から明らかなように、本発明の化
合物は植物成長調節剤として作用することが認められ
た。Tables 1 to 3 show the results of measuring the length of the foliage, the number of foliage and the length of the root. As is clear from the table, the compounds of the present invention were found to act as plant growth regulators.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 ＦＩ Ｃ０７Ｄ 209/20 Ｃ０７Ｄ 209/20 ──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 6 Identification code FI C07D 209/20 C07D 209/20
Claims (3)
基、R2は炭素数１〜４のアルキル基又はヒドロキシアル
キル基を表わす。R3及びR4は（BO）xHであり、ここで、
Ｂは炭素数１〜４のアルキレン基、ｘは１〜５の整数ま
たは非整数を表わす。 Ａ はR5NHR6COO 、 R5CH（NH2）COO 又は であり、ここで、R5はＨ、炭素数１〜４のアルキル基、
CH2（OH）−、CH3SCH2CH2−、 NH2CH2（CH2）3−若しくはHSCH2−を表わし、R6はCH2又
はベンゼン核を表わす。］ で示される新規オキシアルキル化第４アンモニウム化合
物。(1) a general formula,[Where R1Is an alkyl group or alkenyl having 6 to 22 carbon atoms
Group, RTwoIs an alkyl group having 1 to 4 carbon atoms or hydroxyal
Represents a kill group. RThreeAnd RFourIs (BO)xH, where
B is an alkylene group having 1 to 4 carbon atoms, and x is an integer of 1 to 5
Or non-integer. A Is RFiveNHR6COO , RFiveCH (NHTwo) COO OrAnd where RFiveIs H, an alkyl group having 1 to 4 carbon atoms,
CHTwo(OH)-, CHThreeSCHTwoCHTwo−, NHTwoCHTwo(CHTwo)Three-Or HSCHTwo−, R6Is CHTwoor
Represents a benzene nucleus. ] A novel oxyalkylated quaternary ammonium compound represented by the formula:
Stuff.
基、R2炭素数１〜４のアルキル基又はヒドロキシアルキ
ル基を表わす。R3及びR4は（BO）xHであり、ここで、Ｂ
は炭素数１〜４のアルキレン基、ｘは１〜５の整数また
は非整数を表わす。ＹはCl、Br、Ｉ又はＦを表わす。］ で示される第４アンモニウム化合物と、 一般式 R5NHR6COOD……（３）で示される化合物、 一般式 で示される化合物、一般式 で示される化合物、一般式 R5CH（NH2）COOD……（６）で示される化合物、及び一
般式 で示される化合物 ［式中、R5はＨ、炭素数１〜４のアルキル基、 CH2（OH）−、CH3SCH2CH2−、 NH2CH2（CH2）3−若しくはHSCH2−を表わし、R6はCH2 又はベンゼン核を表わす。Ｄはアルカリ金属原子若しく
はアルカリ土類金属原子を表わす。］ からなる群から選ばれた少なくとも１種を、 炭素数１〜６の直鎖または分岐アルコール、メチルエチ
ルケトン、ジメチルスルホキサイド、ジメチルホルムア
ミド、ジオキサン、酢酸エチル、及びシクロヘキサノー
ルからなる群より選ばれた少なくとも１種の溶媒中で、 請求項１記載の一般式（１）で示される新規オキシアル
キル化第４アンモニウム化合物の少量の存在下又は不存
在下で反応させることを特徴とする、請求項１記載の一
般式（１）で示される新規オキシアルキル化第４アンモ
ニウム化合物の製造方法。2. The general formula: [In the formula, R 1 represents an alkyl group or alkenyl group having 6 to 22 carbon atoms, and R 2 represents an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms. R 3 and R 4 are (BO) x H, where B
Represents an alkylene group having 1 to 4 carbon atoms, and x represents an integer of 1 to 5 or a non-integer. Y represents Cl, Br, I or F. A quaternary ammonium compound represented by the following formula: and a compound represented by the general formula R 5 NHR 6 COOD. A compound represented by the general formula A compound represented by the general formula R 5 CH (NH 2 ) COOD ... (6), and a compound represented by the general formula: Wherein R 5 is H, an alkyl group having 1 to 4 carbon atoms, CH 2 (OH) —, CH 3 SCH 2 CH 2 —, NH 2 CH 2 (CH 2 ) 3 — or HSCH 2 —, and R 6 represents CH 2 or a benzene nucleus. D represents an alkali metal atom or an alkaline earth metal atom. At least one selected from the group consisting of linear or branched alcohols having 1 to 6 carbon atoms, methyl ethyl ketone, dimethyl sulfoxide, dimethyl formamide, dioxane, ethyl acetate, and cyclohexanol The reaction is carried out in at least one solvent in the presence or absence of a small amount of the novel oxyalkylated quaternary ammonium compound represented by the general formula (1) according to claim 1. A method for producing a novel oxyalkylated quaternary ammonium compound represented by the general formula (1) described above.
新規オキシアルキル化第４アンモニウム化合物を有効成
分として含有する植物成長調節剤。3. A plant growth regulator comprising the novel oxyalkylated quaternary ammonium compound represented by the general formula (1) according to claim 1 as an active ingredient.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30147588A JP2881443B2 (en) | 1988-11-28 | 1988-11-28 | Novel oxyalkylated quaternary ammonium compound, production method thereof and plant growth regulator containing the same as active ingredient |
| US07/439,080 US5076828A (en) | 1988-11-28 | 1989-11-20 | Oxyalkylated quaternary ammonium compounds and plant growth regulating compositions containing said compounds |
| DE89121723T DE68908105T2 (en) | 1988-11-28 | 1989-11-24 | Oxyalkylated quaternary ammonium compounds, processes for their preparation and plant growth regulators containing them. |
| EP89121723A EP0371406B1 (en) | 1988-11-28 | 1989-11-24 | Oxyalkylated quaternary ammonium compounds, processes for production thereof, and plant growth regulating compositions containing said compounds |
| BR898905978A BR8905978A (en) | 1988-11-28 | 1989-11-28 | OXYALLYCHILATED QUATERNARY AMMONIA COMPOUND, PRODUCTION PROCESS OF THE REFERRED COMPOUND AND PLANT GROWTH REGULATORY COMPOSITION |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30147588A JP2881443B2 (en) | 1988-11-28 | 1988-11-28 | Novel oxyalkylated quaternary ammonium compound, production method thereof and plant growth regulator containing the same as active ingredient |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02145551A JPH02145551A (en) | 1990-06-05 |
| JP2881443B2 true JP2881443B2 (en) | 1999-04-12 |
Family
ID=17897347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30147588A Expired - Fee Related JP2881443B2 (en) | 1988-11-28 | 1988-11-28 | Novel oxyalkylated quaternary ammonium compound, production method thereof and plant growth regulator containing the same as active ingredient |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2881443B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3943661B2 (en) * | 1996-07-11 | 2007-07-11 | 株式会社資生堂 | INDOLE DERIVATIVE AND ROOTING INDUCER CONTAINING THE SAME |
-
1988
- 1988-11-28 JP JP30147588A patent/JP2881443B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02145551A (en) | 1990-06-05 |
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