JPS59157051A - Beta-oxy-alpha-methylenepropionic acid - Google Patents
Beta-oxy-alpha-methylenepropionic acidInfo
- Publication number
- JPS59157051A JPS59157051A JP2939083A JP2939083A JPS59157051A JP S59157051 A JPS59157051 A JP S59157051A JP 2939083 A JP2939083 A JP 2939083A JP 2939083 A JP2939083 A JP 2939083A JP S59157051 A JPS59157051 A JP S59157051A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- beta
- oxy
- alpha
- methylenepropionic
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 9
- -1 methylthiophenyl Chemical group 0.000 claims abstract description 9
- 125000001207 fluorophenyl group Chemical group 0.000 claims abstract description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 230000008635 plant growth Effects 0.000 abstract description 5
- 150000001555 benzenes Chemical class 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000005648 plant growth regulator Substances 0.000 abstract description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- RLCRNCFDHDQTLF-UHFFFAOYSA-N 3,3-dibromo-2-methylpropanoic acid Chemical compound BrC(Br)C(C)C(O)=O RLCRNCFDHDQTLF-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 206010053759 Growth retardation Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NSKMOMZKJAGWHN-UHFFFAOYSA-N 2-[(4-fluorophenoxy)methyl]prop-2-enoic acid Chemical compound OC(=O)C(=C)COC1=CC=C(F)C=C1 NSKMOMZKJAGWHN-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002373 plant growth inhibitor Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
- ZAGGZBMIXMCTKA-UHFFFAOYSA-N 2-(phenoxymethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)COC1=CC=CC=C1 ZAGGZBMIXMCTKA-UHFFFAOYSA-N 0.000 description 1
- POEXKURDQFJBLF-UHFFFAOYSA-N 2-(phenylsulfanylmethyl)prop-2-enoic acid Chemical compound OC(=O)C(=C)CSC1=CC=CC=C1 POEXKURDQFJBLF-UHFFFAOYSA-N 0.000 description 1
- UTKHLTRHMHQVGS-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)CSC2=C1 UTKHLTRHMHQVGS-UHFFFAOYSA-N 0.000 description 1
- VIIIJFZJKFXOGG-UHFFFAOYSA-N 3-methylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C)=CC2=C1 VIIIJFZJKFXOGG-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
- 240000001970 Raphanus sativus var. sativus Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
この発明は新規なβ−オキシ−α−メチレンプロピオン
酸エステルに関するものであり植物生長抑制剤として有
用である。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) This invention relates to a novel β-oxy-α-methylenepropionate ester, which is useful as a plant growth inhibitor.
（従来技術）
β−フェノキシ−α−メチレンプロピオン酸は、３−メ
チルクマリンを合成する中間体として報告されている。(Prior Art) β-phenoxy-α-methylenepropionic acid has been reported as an intermediate for synthesizing 3-methylcoumarin.
また、β−フェニルチオ−α−メチレンプロピオン酸は
、チオクロマン−３−カルボン酸を合成するための中間
体として報告されている。（Ｓｗａｍｉｎａｔｈａｎ等
、５Ｓｙｎｔｈｅｓｉｓ Ｃｏ＋ｎｍｕｎｉｃａｔｉｏ
ｎｓ、 ５ｅｐｔ。１９７５． ｐ、 ５９９゜同Ｊｕ
ｎｅ １９７６、 ｐ、 ４０９ ）これらの文献には
４−メチルなど、いくつかの核置換法も記されている。Furthermore, β-phenylthio-α-methylenepropionic acid has been reported as an intermediate for synthesizing thiochroman-3-carboxylic acid. (Swaminathan et al., 5Synthesis Co+nmunication
ns, 5ept. 1975. p, 599゜ Same Ju
ne 1976, p. 409) Several nuclear substitution methods, such as 4-methyl, are also described in these documents.
しかし、ベンゼン核が本発明の化合物のように置換され
たβ−オキシ−α−メチレンプロピオン酸につ℃・ては
記載がなく、植物に対する作用も記されていない。However, there is no description of β-oxy-α-methylenepropionic acid in which the benzene nucleus is substituted as in the compound of the present invention, nor is there any description of its effects on plants.
また、特公昭５２−１９７２号公報には、植物生長調整
剤としである種のα−置換アクリル酸誘導体が記されて
いるが、これらの化合物はチオエステルや鎖式チオエー
テル２４ｑの構造をもつ物質であり、置換フェニルエー
テル型のイｊ４造をもつ化合物は記されていない。Furthermore, Japanese Patent Publication No. 52-1972 describes certain α-substituted acrylic acid derivatives as plant growth regulators, but these compounds are substances with a thioester or chain thioether 24q structure. However, compounds with a substituted phenyl ether type ij4 structure are not described.
（発明の目的）
本発明者は、有用な対植物活性をもつ化合物を見出すべ
（研究し、β−オキシ−α−メチレンプロピオン酸に属
する一群の新規化合物を合成し、それらの植物に対する
作用を確認し、本発明を完成した。(Objective of the Invention) The present inventor conducted research to discover compounds with useful activity against plants, synthesized a group of new compounds belonging to β-oxy-α-methylenepropionic acid, and investigated their effects on plants. This was confirmed and the present invention was completed.
即ち、本発明は対植物活性の如き有用な性質をもつ化合
物を新たに創り出すことを目的とする。That is, the purpose of the present invention is to create a new compound having useful properties such as activity against plants.
（発明の構成と例示）
本発明は一般式Ａ−ＯＣＨ２ＣＣ０ＯＨで表わされ１
ＯＨ２
る新規なβ−オキシ−α−メチレンプロピオン酸である
。(Structure and illustration of the invention) The present invention is a novel β-oxy-α-methylenepropionic acid represented by the general formula A-OCH2CCOOH.
こ〜でＡは、特定の基で置換されたベンゼン核を宮む基
である。ベンゼン核上の置換基は−Ｆ 、 −８ＣＨ３
、−ＮＨ−Ｃ１０Ｈ７、−ＣｓＨｓまたは−（ＣＨ２）
４−であり、従って本発明の化合物は上の一般式におい
てＡがそれぞれフルオロフェニル、メチルチオフェニル
、ナフチルアミノフェニル、ビフェニリル及びテトラヒ
ドロナフチルである化合物である。In ~, A is a group that supports a benzene nucleus substituted with a specific group. The substituents on the benzene nucleus are -F, -8CH3
, -NH-C10H7, -CsHs or -(CH2)
4- and thus the compounds of the invention are those in the above general formula in which A is fluorophenyl, methylthiophenyl, naphthylaminophenyl, biphenylyl and tetrahydronaphthyl, respectively.
（合成法）
本発明の化合物は、次のような方法で容易に合成するこ
とができる。即ち、Ａ−ＯＨ（Ａは前記と同じものを意
味する）で表わされるフェノール類（１）を、例えばエ
タノールのような溶媒及びアルカリ（例えば３倍モルの
Ｎ（ＬＯＨ）の存在下にβ、β−ジブロモイソ酪酸（２
）と反応させることによってオキシにＡのついたβ−オ
キシ−α−メチレンプロピオン酸（３）を得る。(Synthesis method) The compound of the present invention can be easily synthesized by the following method. That is, the phenol (1) represented by A-OH (A means the same as above) is β, β-dibromoisobutyric acid (2
) to obtain β-oxy-α-methylenepropionic acid (3) with A attached to oxy.
合成法の更に詳細な具体例は製造例により示し、またそ
れにより得られた各物質の代表的な物性値は第１表に示
した。A more detailed example of the synthesis method is shown in the production example, and typical physical property values of each substance obtained thereby are shown in Table 1.
（発明の作用効果） 本発明の物質の植物に対する作用を使用例に示した。(Effects of invention) The effects of the substances of the present invention on plants are shown in usage examples.
チオエステルや鎖式チオエーテル構造をもつα−置換ア
クリル酸誘導体が比較的低温度において植物の生長促進
、高濃度において落葉促進作用をもつものであったのと
異なり、本発明の物質は植物の生長抑制作用をもつ。Unlike thioesters and α-substituted acrylic acid derivatives with chain thioether structures, which promote plant growth at relatively low temperatures and promote defoliation at high concentrations, the substance of the present invention inhibits plant growth. It has an effect.
このように植物生長抑制剤として有用な化合物が本発明
により提供された。Thus, the present invention provides a compound useful as a plant growth inhibitor.
製造例１、２−メチレン−３−（４−フルオロフェノキ
シ）プロピオン酸の合成
１、３５ ｇの４−フルオロフェノキシ（１２ｍｍｏ
ｌ ）を無水エタノール２０ｒｒｔｌに溶解する。Production Example 1, Synthesis of 2-methylene-3-(4-fluorophenoxy)propionic acid 1, 35 g of 4-fluorophenoxy (12 mmo
l) in 20 rrtl of absolute ethanol.
次に、粉末の水酸化ナトリウム０．４８ｇ、１２ｍｍｏ
ｌ ）を加え、しばらく加熱還流する。反応系が均一
溶液になったことを確認した後、０．９８Ｉのβ、β′
−ジブロモイノ酪＃ （４ｍｍｏｌ ）の無水エタノー
ル溶液（１０ｍｌ）を滴下し、還流条件タノールを減圧
下留去し、残渣に水を加える。Next, 0.48 g of powdered sodium hydroxide, 12 mmo
1) and heated under reflux for a while. After confirming that the reaction system has become a homogeneous solution, 0.98I β, β'
-Anhydrous ethanol solution (10 ml) of dibromoinobutyric acid # (4 mmol) was added dropwise, reflux condition, tanol was distilled off under reduced pressure, and water was added to the residue.
１０％塩酸で酸性化（ｐＨ２〜３）し、ジエチルエーテ
ルで抽出する◇エーテル層を飽和炭酸水素ナトリウムで
抽出し、アルカリ抽出層を再び濃塩酸で酸性化すると白
色結晶が析出する。Acidify with 10% hydrochloric acid (pH 2-3) and extract with diethyl ether. ◇Extract the ether layer with saturated sodium bicarbonate, and acidify the alkaline extracted layer again with concentrated hydrochloric acid to precipitate white crystals.
吸引１過により析出結晶を分離し、水洗後減圧下乾燥す
る。得られた粗生成物を薄層クロマトグラフィー（ワコ
ーゲル■Ｂ−５Ｆ、ヘキサン：ｒＸｐｍ−ｃチＡ／：
７ ： ３で展開）で精製し、０．２１１（５３％収率
）の２−メチレン−３−（４−フルオロフェノキシ）プ
ロピオン酸（化合＊Ｊｎｌ）を得た。The precipitated crystals are separated by suction, washed with water, and dried under reduced pressure. The obtained crude product was subjected to thin layer chromatography (Wakogel B-5F, hexane: rXpm-c A/:
7:3) to obtain 0.211 (53% yield) of 2-methylene-3-(4-fluorophenoxy)propionic acid (compound *Jnl).
同様の方法により、下記の化合物 Ａ ０ＣＨ２ＣＣＯＯＨを得た。By a similar method, the following compounds A0CH2CCOOH was obtained.
Ｈ２
Ａ＝ＣＨｓ ｓ＜二〉← （化合物層２）使用例 （植
物生長抑制作用の試験）
タルク５０部、ベントナイト２５都、ソルボ−ルー９０
４７（東邦化学工栗株式会社製界面活性剤）２部、ソル
ボ−ルー５０３９（同上）３部を良く混合し、キャリヤ
ーとした。被験化合物をそれぞれ５０部と前記キャリヤ
ー２００部を混合し、２０％水相剤を作った。この水相
剤を純水に分散させ虐定磯度とした。別のシャーレで催
芽させたイネ、タイヌビエ、二十日ダイコン種子を上配
水和剤分散麩に投入し、２５℃の照明付属（＠通で７日
ＩＬ４ｉ腎菌して生長程度を観察した。H2 A=CHs s<2>← (Compound layer 2) Usage example (Test for plant growth inhibitory effect) Talc 50 parts, bentonite 25 parts, Sorbo-roux 90 parts
47 (surfactant manufactured by Toho Kagaku Kuri Co., Ltd.) and 3 parts of Sorbo-Rue 5039 (same as above) were mixed well to form a carrier. 50 parts of each of the test compounds and 200 parts of the carrier were mixed to prepare a 20% aqueous phase agent. This aqueous phase agent was dispersed in pure water to obtain an abrasive surfactant. Seeds of rice, Japanese millet, and 20-day Japanese radish germinated in separate Petri dishes were placed in a top-dispersed hydrating powder, and the growth was observed using IL4i kidney bacteria for 7 days at 25° C. with lighting attached.
結果を第２衣に示す。The results are shown in the second layer.
第２表
衣示法 無影曽＝１．２５％生長抑制＝２゜５０％生長
側１制＝３．７５％生量抑
制＝４，１００％生長抑制＝５
第２六に示したように、本発明に用いられた化合物は植
物の生長を顕著に抑制し、′除草剤への利用が期待され
る。2nd display method Mukageso = 1.25% growth suppression = 2゜50% growth side 1 system = 3.75% growth suppression = 4,100% growth suppression = 5 As shown in Chapter 26 The compounds used in the present invention significantly inhibit plant growth and are expected to be used as herbicides.
Claims (1)
、ナフチルアミノフェニル、ビフェニリル、又はテトラ
ヒドロナフチルであるベンゼン核を含む基を意味する。 〕 で表わされるβ−オキシ−α−メチレンプロピオン酸。[Claims] General formula A-OCHz, CCOOH 1 H2 [wherein A- means a group containing a benzene nucleus such as fluorophenyl, methylthiophenyl, naphthylaminophenyl, biphenylyl, or tetrahydronaphthyl. ] β-oxy-α-methylenepropionic acid represented by:
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2939083A JPS59157051A (en) | 1983-02-25 | 1983-02-25 | Beta-oxy-alpha-methylenepropionic acid |
| EP84100497A EP0117412A1 (en) | 1983-01-18 | 1984-01-18 | Propene derivatives and their use as plant growth inhibitors |
| EP84100585A EP0118685A1 (en) | 1983-02-07 | 1984-01-20 | Propene derivatives and their use as plant growth inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2939083A JPS59157051A (en) | 1983-02-25 | 1983-02-25 | Beta-oxy-alpha-methylenepropionic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59157051A true JPS59157051A (en) | 1984-09-06 |
| JPH0261929B2 JPH0261929B2 (en) | 1990-12-21 |
Family
ID=12274810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2939083A Granted JPS59157051A (en) | 1983-01-18 | 1983-02-25 | Beta-oxy-alpha-methylenepropionic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59157051A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5753438A (en) * | 1980-07-29 | 1982-03-30 | Basf Ag | Manufacture of 2-aryloxy-acrylic acid compound |
| JPS57140771A (en) * | 1981-01-12 | 1982-08-31 | Ici Australia Ltd | Herbicidal compounds and composition and use |
| JPS59144731A (en) * | 1983-02-07 | 1984-08-18 | Daicel Chem Ind Ltd | Beta-substituted phenoxy-alpha-methylenepropionic acid derivative |
-
1983
- 1983-02-25 JP JP2939083A patent/JPS59157051A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5753438A (en) * | 1980-07-29 | 1982-03-30 | Basf Ag | Manufacture of 2-aryloxy-acrylic acid compound |
| JPS57140771A (en) * | 1981-01-12 | 1982-08-31 | Ici Australia Ltd | Herbicidal compounds and composition and use |
| JPS59144731A (en) * | 1983-02-07 | 1984-08-18 | Daicel Chem Ind Ltd | Beta-substituted phenoxy-alpha-methylenepropionic acid derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0261929B2 (en) | 1990-12-21 |
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