JPH0436146B2 - - Google Patents
Info
- Publication number
- JPH0436146B2 JPH0436146B2 JP15617783A JP15617783A JPH0436146B2 JP H0436146 B2 JPH0436146 B2 JP H0436146B2 JP 15617783 A JP15617783 A JP 15617783A JP 15617783 A JP15617783 A JP 15617783A JP H0436146 B2 JPH0436146 B2 JP H0436146B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- dihalo
- nitrophenol
- formula
- represented
- 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
Links
- 238000004519 manufacturing process Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 ethylene halohydrin Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LRHFGBDYKMSVMK-UHFFFAOYSA-N 7-nitro-2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound O1CCOC2=C1C=C(O)C([N+]([O-])=O)=C2 LRHFGBDYKMSVMK-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OFAPWTOOMSVMIU-UHFFFAOYSA-N 2,4-dichloro-5-nitrophenol Chemical compound OC1=CC([N+]([O-])=O)=C(Cl)C=C1Cl OFAPWTOOMSVMIU-UHFFFAOYSA-N 0.000 description 1
- QNULZVZLSYAFSP-UHFFFAOYSA-N 2-(2,4-dichloro-5-nitrophenoxy)ethanol Chemical compound OCCOC1=CC([N+]([O-])=O)=C(Cl)C=C1Cl QNULZVZLSYAFSP-UHFFFAOYSA-N 0.000 description 1
- NAWVMCKMQMJQMF-UHFFFAOYSA-N 2-chloro-4-fluoro-5-nitrophenol Chemical compound OC1=CC([N+]([O-])=O)=C(F)C=C1Cl NAWVMCKMQMJQMF-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 241000219095 Vitis Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、一般式〔〕
〔式中、ＸおよびＹは同一または相異なり、ハ
ロゲン原子を表わす。〕
で示されるβ−（２，４−ジハロ−５−ニトロフ
エノキシ）エタノール（以下、本発明化合物と記
す。）およびその製造法に関する。
上記一般式〔〕で示される本発明化合物は植
物病害防除剤の有効成分の中間体である。すなわ
ち、本発明化合物をアルカリ金属水酸化物または
金属フツ化物などの無機塩基の存在下で加熱して
得られる４，５−エチレンジオキシ−２−ニトロ
フエノールをＯ−エチル Ｎ−sec−プチル チ
オリン酸アミドクロリドを反応させることによつ
て製造することができるＯ−エチル Ｏ−４，５
−エチレンジオキシ−２−ニトロフエニル Ｎ−
sec−プチル ホスホロアミドチオエートは、植
物病害防除剤の有効成分であり、べと病や疫病等
の植物病害に対して防除効果を有する。
本発明者らは、一般式〔〕で示される本発明
化合物の製造法について検討した結果、一般式
〔〕
〔式中、ＸおよびＹは前記と同一の意味を表わ
す。〕
で示される２，４−ジハロ−５−ニトロフエノー
ルと一般式〔〕
ZCH2CH2OH 〔〕
〔式中、Ｚはハロゲン原子を表わす。〕
で示されるエチレンハロヒドリンとを溶媒中、無
機塩基の存在下に反応させることによつて本発明
化合物を製造できることを見出した。
次に、本発明化合物の製造法について詳細に説
明する。
本発明製造法において、一般式〔〕で示され
るエチレンハロヒドリンとしては、例えばエチレ
ンクロロヒドリンまたはエチレンブロモヒドリン
などが、挙げられ、その使用量は通常、一般式
〔〕で示される２，４−ジハロ−５−ニトロフ
エノールに対して１〜５当量である。溶媒として
は、例えばアセトニトリル、Ｎ，Ｎ−ジメチルホ
ルムアミド、ジメチルスルホキシドなどが挙げら
れる。無機塩基としては、例えば水酸化ナトリウ
ム、炭酸カリウムなどが挙げられ、その使用量は
通常、一般式〔〕で示される２，４−ジハロ−
５−ニトロフエノールに対して１〜５当量であ
る。反応温度は通常60〜150℃であり、反応時間
は通常１〜24時間である。
反応終了後は、通常の後処理を行ない、必要な
らばクロマトグラフイ−、再結晶等によつて精製
する。
原料化合物である上記一般式（）で示される
２，４−ジハロ−５−ニトロフエノールは、例え
ばJ.Chem.Soc.，1929 517〜520に記載の製造法
によつて製造することができる。
次に実施例を示す。
実施例 １
２，４−ジクロロ−５−ニトロフエノール
2.08gをアセトニトリル10mlに溶かし、炭酸カリ
ウム粉末2.0gを加えて、加熱還流下に、エチレン
ブロモヒドリン5.0gを加え、さらに２時間反応さ
せた。冷却後、結晶を別し、液を濃縮した。
残分に酢酸エチル50mlを加え、２％水酸化ナトリ
ウム水溶液ついで水での洗浄を繰り返した後、酢
酸エチルを減圧留去し、生じた結晶をベンゼンで
再結晶し、β−（２，４−ジクロロ−５−ニトロ
フエノキシ）エタノール2.42gを得た。
m.p.99〜100℃
実施例 ２
２−クロロ−４−フルオロ−５−ニトロフエノ
ール10.51gをＮ，Ｎ−ジメチルホルムアミド60ml
に溶かし、エチレンクロロヒドリン20gを加え
て、100℃に加熱し、炭酸カリウム粉末8.5gを加
えた。100〜120℃に６時間保つた後、冷却し、つ
いで実施例１と同様に処理してβ−（２−クロロ
−４−フルオロ−５−ニトロフエノキシ）エタノ
ール11.6gを得た。
m.p.80〜82℃
次に、参考のために４，５−エチレンンジオキ
シ−２−ニトロフエノールの製造例を示す。
参考製造例 １
β−（２，４−ジクロロ−５−ニトロフエノキ
シ）エタノール2.0gをジメチルスルホキシド10ml
に溶かし、塩化第一銅0.1gを加えて100℃に加熱
し、さらに水酸化ナトリウム粉末1.5gを加え130
〜150℃に１時間保つた。冷却後、氷水100ml中に
注ぎ、酢酸エチル100mlを用いて二度抽出し、抽
出液を水洗後硫酸マグネシウム乾燥した。酢酸エ
チルを減圧留去してから、シリカゲルカラムクロ
マトグラフイーで精製して４，５−エチレンジオ
キシ−２−ニトロフエノール0.67gを得た。 m.
p.170〜173℃
参考製造例 ２
β−（２−クロロ−４−フルオロ−５−ニトロ
フエノキシ）エタノール2.0gをジメチルスルホキ
シド10mlに溶かし、水酸化カリウム粉末1.40gを
加えて加熱し、120〜130℃に３時間保つた。冷却
後、氷水100ml中に注ぎ、酢酸エチル100mlを用い
て二度抽出し、抽出液を水洗後、硫酸マグネシウ
ム乾燥した。酢酸エチルを減圧留去してから、シ
リカゲルカラムクロマトグラフイーで精製して
４，５−エチレンジオキシ−２−ニトロフエノー
ル0.72gを得た。 m.p.170〜173℃
次に参考のためにＯ−エチル Ｏ−４，５−エ
チレンジオキシ−２−ニトロフエニル Ｎ−sec
−プチル ホスホロアミドチオエートの製造例と
試験例を示す。
参考製造例 ３
４，５−エチレンジオキシ−２−ニトロフエノ
ール（1.97g，10ミリモル）をアセトニトリル100
mlに溶かし、これに無水炭酸カリウム末（1.40g）
と塩化第一銅（10mg）とを加えて40〜50℃で30分
攪拌した。ついでＯ−エチル Ｎ−sec−プチル
チオノリン酸アミドクロリド（2.2g，10ミリモ
ル）を40分で滴下した後、３時間攪拌還流した。
無機塩を別した、アセトニトリルを減圧留去
し、残分をトルエンに溶かし、希酸水溶液、水希
アルカリ水溶液、水の順で洗浄し、無水硫酸マグ
ネシウムで乾燥した。トルエンを減圧留去し、さ
らにシリカゲルカラムクロマトグラフイーで精製
してＯ−エチル Ｏ−４，５−エチレンジオキシ
−２−ニトロフエニル Ｎ−sec−プチル ホス
ホロアミドチオエート2.33gを得た。
m.p.59〜61℃
参考試験例 ブドウベと病防除効果試験（治療効
果）
プラスチツクポツトに砂壤土を詰め、ブドウ
（ネオマスカツトの種）を播種し、温室内で50日
間育成した。第４〜５本葉が展開したブドウの幼
苗にブドウベと病菌の胞子懸濁液を噴霧接種し
た。接種後25℃、多湿下で１日間育成し、乳剤に
した供試化合物を水で希釈して所定濃度にし、そ
れを葉面に充分付着するように茎葉散布した。散
布後23℃温室内で10時間育成し、防除効力を調査
した。防除効力は、調査時の供試植物の発病状態
すなわち葉、茎等の菌叢、病斑の程度を肉眼観察
し、菌叢、病斑が全く認められなければ「５」、
10％程度認められれば「４」、30％程度認められ
れば「３」、50％程度認められれば「２」、70％程
度認められれば「１」、それ以上で化合物を供試
していない場合の発病状態と差が認められなけれ
ば「０」として、０〜５の６段階に評価し、０，
１，２，３，４，５で表示した。
なお、比較対照にクロロタロニルおよびアルミ
ニウムトリス（エチルホスホネート）を用いた。
その結果を第２表に示す。
The present invention is based on the general formula [] [In the formula, X and Y are the same or different and represent a halogen atom. ] The present invention relates to β-(2,4-dihalo-5-nitrophenoxy)ethanol (hereinafter referred to as the compound of the present invention) represented by the following and a method for producing the same. The compound of the present invention represented by the above general formula [] is an intermediate for the active ingredient of a plant disease control agent. That is, 4,5-ethylenedioxy-2-nitrophenol obtained by heating the compound of the present invention in the presence of an inorganic base such as an alkali metal hydroxide or metal fluoride is converted into O-ethyl N-sec-butyl thioline. O-ethyl O-4,5 which can be produced by reacting acid amide chloride
-ethylenedioxy-2-nitrophenyl N-
sec-butyl phosphoroamide thioate is an active ingredient of a plant disease control agent, and has a control effect on plant diseases such as downy mildew and late blight. As a result of studying the method for producing the compound of the present invention represented by the general formula [], the present inventors found that the general formula [] [In the formula, X and Y represent the same meanings as above. ] 2,4-dihalo-5-nitrophenol represented by the general formula [] ZCH 2 CH 2 OH [] [wherein Z represents a halogen atom. ] It has been found that the compound of the present invention can be produced by reacting ethylene halohydrin represented by the following in a solvent in the presence of an inorganic base. Next, the method for producing the compound of the present invention will be explained in detail. In the production method of the present invention, the ethylene halohydrin represented by the general formula [] includes, for example, ethylene chlorohydrin or ethylene bromohydrin, and the amount used is usually 2 as shown by the general formula []. , 1 to 5 equivalents relative to 4-dihalo-5-nitrophenol. Examples of the solvent include acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, and the like. Examples of the inorganic base include sodium hydroxide and potassium carbonate, and the amount used is usually 2,4-dihalo-
It is 1 to 5 equivalents relative to 5-nitrophenol. The reaction temperature is usually 60 to 150°C, and the reaction time is usually 1 to 24 hours. After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, recrystallization, etc. The raw material compound 2,4-dihalo-5-nitrophenol represented by the above general formula () can be produced, for example, by the production method described in J.Chem.Soc., 1929 517-520. Next, examples will be shown. Example 1 2,4-dichloro-5-nitrophenol
2.08 g was dissolved in 10 ml of acetonitrile, 2.0 g of potassium carbonate powder was added, and while heating under reflux, 5.0 g of ethylene bromohydrin was added, and the reaction was further allowed to proceed for 2 hours. After cooling, the crystals were separated and the liquid was concentrated.
After adding 50 ml of ethyl acetate to the residue and repeating washing with a 2% aqueous sodium hydroxide solution and then water, ethyl acetate was distilled off under reduced pressure, and the resulting crystals were recrystallized from benzene to give β-(2,4- 2.42 g of dichloro-5-nitrophenoxy)ethanol was obtained. mp99-100℃ Example 2 10.51g of 2-chloro-4-fluoro-5-nitrophenol was mixed with 60ml of N,N-dimethylformamide.
20g of ethylene chlorohydrin was added, heated to 100°C, and 8.5g of potassium carbonate powder was added. After being kept at 100-120°C for 6 hours, it was cooled and then treated in the same manner as in Example 1 to obtain 11.6 g of β-(2-chloro-4-fluoro-5-nitrophenoxy)ethanol. mp80-82°C Next, a production example of 4,5-ethylenedioxy-2-nitrophenol will be shown for reference. Reference production example 1 2.0g of β-(2,4-dichloro-5-nitrophenoxy)ethanol and 10ml of dimethyl sulfoxide
Add 0.1g of cuprous chloride and heat to 100℃, then add 1.5g of sodium hydroxide powder to 130℃.
It was kept at ~150°C for 1 hour. After cooling, the mixture was poured into 100 ml of ice water, extracted twice with 100 ml of ethyl acetate, and the extract was washed with water and dried over magnesium sulfate. After ethyl acetate was distilled off under reduced pressure, the residue was purified by silica gel column chromatography to obtain 0.67 g of 4,5-ethylenedioxy-2-nitrophenol. m.
p.170~173℃ Reference production example 2 Dissolve 2.0g of β-(2-chloro-4-fluoro-5-nitrophenoxy)ethanol in 10ml of dimethyl sulfoxide, add 1.40g of potassium hydroxide powder, and heat to 120~130℃. It was kept at ℃ for 3 hours. After cooling, it was poured into 100 ml of ice water and extracted twice using 100 ml of ethyl acetate. The extract was washed with water and dried over magnesium sulfate. After ethyl acetate was distilled off under reduced pressure, the residue was purified by silica gel column chromatography to obtain 0.72 g of 4,5-ethylenedioxy-2-nitrophenol. mp170~173℃ Next, for reference, O-ethyl O-4,5-ethylenedioxy-2-nitrophenyl N-sec
-Production examples and test examples of butyl phosphoroamide thioate are shown. Reference production example 3 4,5-ethylenedioxy-2-nitrophenol (1.97 g, 10 mmol) was dissolved in acetonitrile 100
ml and add anhydrous potassium carbonate powder (1.40g) to this.
and cuprous chloride (10 mg) were added and stirred at 40 to 50°C for 30 minutes. Then, O-ethyl N-sec-butyl thionolamide chloride (2.2 g, 10 mmol) was added dropwise over 40 minutes, followed by stirring and refluxing for 3 hours.
After the inorganic salts were separated, the acetonitrile was distilled off under reduced pressure, and the residue was dissolved in toluene, washed successively with a dilute aqueous acid solution, a dilute aqueous alkali solution, and water, and dried over anhydrous magnesium sulfate. Toluene was distilled off under reduced pressure, and the residue was further purified by silica gel column chromatography to obtain 2.33 g of O-ethyl O-4,5-ethylenedioxy-2-nitrophenyl N-sec-butyl phosphoroamide thioate. mp59-61℃ Reference test example Grapevine disease control effect test (therapeutic effect) Plastic pots were filled with sandy soil, grapes (neomuscatus seeds) were sown, and grown in a greenhouse for 50 days. A spore suspension of grapevine and the disease fungus was spray inoculated onto young grape seedlings in which the 4th to 5th true leaves had developed. After inoculation, the plants were grown for 1 day at 25° C. under humid conditions, and an emulsion of the test compound was diluted with water to a predetermined concentration and sprayed on the foliage to ensure sufficient adhesion to the leaf surface. After spraying, the plants were grown in a greenhouse at 23°C for 10 hours, and their pesticidal efficacy was investigated. The control efficacy is determined by visually observing the disease state of the test plants at the time of the survey, that is, the degree of bacterial flora and lesions on leaves, stems, etc., and if no bacterial flora or lesions are observed, it is rated "5".
If about 10% is observed, it is ``4'', if about 30% is observed, it is ``3'', if about 50% is observed, it is ``2'', if about 70% is observed, it is ``1'', and if the compound is not tested if it is higher than that. If there is no difference from the disease onset state, it is evaluated as "0" and evaluated on a scale of 0 to 5.
Displayed as 1, 2, 3, 4, 5. Note that chlorothalonil and aluminum tris(ethylphosphonate) were used for comparison.
The results are shown in Table 2.
【表】【table】
Claims (1)
ロゲン原子を表わす。〕 で示されるβ−（２，４−ジハロ−５−ニトロフ
エノキシ）エタノール。 ２ 一般式 〔式中、ＸおよびＹは同一または相異なり、ハ
ロゲン原子を表わす。〕 で示される２，４−ジハロ−５−ニトロフエノ−
ルと一般式 ZCH2CH2OH 〔式中、Ｚはハロゲン原子を表わす。〕 で示されるエチレンハロヒドリンとを無機塩基の
存在下に反応させることを特徴とする一般式 〔式中、ＸおよびＹは前記と同一の意味を表わ
す。〕 で示されるβ−（２，４−ジハロ−５−ニトロフ
エノキシ）エタノールの製造法。[Claims] 1. General formula [In the formula, X and Y are the same or different and represent a halogen atom. ] β-(2,4-dihalo-5-nitrophenoxy)ethanol represented by: 2 General formula [In the formula, X and Y are the same or different and represent a halogen atom. ] 2,4-dihalo-5-nitropheno-
and the general formula ZCH 2 CH 2 OH [wherein, Z represents a halogen atom]. ] A general formula characterized by reacting ethylene halohydrin represented by in the presence of an inorganic base. [In the formula, X and Y represent the same meanings as above. ] A method for producing β-(2,4-dihalo-5-nitrophenoxy)ethanol shown below.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617783A JPS6048949A (en) | 1983-08-25 | 1983-08-25 | Beta-(2,4-dihalo-5-nitrophenoxyoethanol and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15617783A JPS6048949A (en) | 1983-08-25 | 1983-08-25 | Beta-(2,4-dihalo-5-nitrophenoxyoethanol and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6048949A JPS6048949A (en) | 1985-03-16 |
| JPH0436146B2 true JPH0436146B2 (en) | 1992-06-15 |
Family
ID=15622034
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15617783A Granted JPS6048949A (en) | 1983-08-25 | 1983-08-25 | Beta-(2,4-dihalo-5-nitrophenoxyoethanol and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6048949A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO172846C (en) * | 1987-12-25 | 1993-09-15 | Daiichi Seiyaku Co | PROCEDURE FOR PREPARING 7,8-DIHALOGEN-3-METHYL-2,3-DIHYDRO-2M-BENZOCSAZINE DERIVATIVES AND PROPOXYBENZEN DERIVATIVES FOR EXERCISING THE PROCEDURE. |
-
1983
- 1983-08-25 JP JP15617783A patent/JPS6048949A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6048949A (en) | 1985-03-16 |
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