JPH0439465B2 - - Google Patents
Info
- Publication number
- JPH0439465B2 JPH0439465B2 JP14843583A JP14843583A JPH0439465B2 JP H0439465 B2 JPH0439465 B2 JP H0439465B2 JP 14843583 A JP14843583 A JP 14843583A JP 14843583 A JP14843583 A JP 14843583A JP H0439465 B2 JPH0439465 B2 JP H0439465B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ethylenedioxy
- ethylenedioxyphenyl
- acetate
- nitrophenyl
- 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
- VUFRIRUMGMOOJQ-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-yl acetate Chemical compound O1CCOC2=CC(OC(=O)C)=CC=C21 VUFRIRUMGMOOJQ-UHFFFAOYSA-N 0.000 claims 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 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- DNRUBISPKVBWIS-UHFFFAOYSA-N (7-nitro-2,3-dihydro-1,4-benzodioxin-6-yl) acetate Chemical compound O1CCOC2=C1C=C(OC(=O)C)C([N+]([O-])=O)=C2 DNRUBISPKVBWIS-UHFFFAOYSA-N 0.000 description 3
- -1 3,4-ethylenedioxyphenylmethylketone Chemical compound 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241000219095 Vitis Species 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- HGVWMTAIIYNQSI-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone Chemical compound O1CCOC2=CC(C(=O)C)=CC=C21 HGVWMTAIIYNQSI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DBPZCGJRCAALLW-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ol Chemical compound O1CCOC2=CC(O)=CC=C21 DBPZCGJRCAALLW-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 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
- 238000001816 cooling Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- NFZJYJJVHFGPSI-UHFFFAOYSA-H dialuminum;ethyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [Al+3].[Al+3].CCP([O-])([O-])=O.CCP([O-])([O-])=O.CCP([O-])([O-])=O NFZJYJJVHFGPSI-UHFFFAOYSA-H 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
【発明の詳細な説明】
本発明は、4,5−エチレンジオキシ−2−ニ
トロフエノールおよびその製造法に関する。
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、例えば
O−エチル N−sec−ブチル チオノリン酸ア
ミドクロリドと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−ブチ
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
に対して防除効力を有する。
本発明者らは、4,5−エチレンジオキシ−2
−ニトロフエノールの製造法について検討した結
果、酢酸3,4−エチレンジオキシフエニルをニ
トロ化して加水分解することによつて高収率で高
純度の4,5−エチレンジオキシ−2−ニトロフ
エノールを製造することが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述べ
る。
酢酸3,4−エチレンジオキシフエニルのニト
ロ化は、例えば硫酸と硝酸の混酸、酢酸と硝酸の
混酸、発煙硝酸、ハロゲン化炭化水素溶媒下硝酸
を用いて、通常0〜10℃で、12時間以内で反応さ
せて行なう。反応終了後は常法により酢酸4,5
−エチレンジオキシ−2−ニトロフエニルが得ら
れる。
上述のようにして得られた酢酸4,5−エチレ
ンジオキシ−2−ニトロフエニルの加水分解は、
アルカリまたは酸の触媒存在下で行なう。アルカ
リ触媒での加水分解は、例えば、酢酸4,5−エ
チレンジオキシ−2−ニトロフエニルのアルコー
ル溶液に、水酸化ナトリウムなどのアルカリ水溶
液を加えて通常40〜60℃で1〜5時間反応させて
行なうか、またはアルコラートのアルコール溶液
に酢酸4,5−エチレンジオキシ−2−ニトロフ
エニルを加えて、通常1〜7時間加熱還流して行
なう。酸触媒での加水分解は、例えば酢酸4,5
−ジエチレンジオキシ−2−ニトロフエニルのア
ルコール溶液に、塩酸または硫酸などを触媒とし
て加えて、通常、60〜80℃で4〜8時間反応させ
て行なう。いずれも反応終了後は中和し、必要な
らば溶媒を留去して得られた結晶を集し、水洗
後乾燥することにより、4,5−エチレンジオキ
シ−2−ニトロフエノールが得られる。
原料化合物である酢酸3,4−エチレンジオキ
シフエニルは、3,4−エチレンジオキシフエニ
ルメチルケトンを過酢酸、メタクロロ過安息香酸
等の過酸と反応させるか、または3,4−エチレ
ンジオキシフエノールを無水酢酸、塩化アセチル
等のアセチル化剤と反応させることにより製造す
ることができる。なお、3,4−エチレンジオキ
シフエニルメチルケトンおよび3,4−エチレン
ジオキシフエノールは、J.Chem.Soc.,19573445
〜3447に記載されている方法により製造すること
ができる。
実施例
酢酸3,4−エチレンジオキシフエニル(5.93
g、30.5mmol)を酢酸15mlに溶かし、4〜7℃
に保ちつつ撹拌下に硝酸(d=1.50)2.0mlと酢
酸3.0mlの混合液を30分間かけて滴下した。滴下
終了後室温にもどし、反応液に氷水にあけ結晶を
集、水洗し、酢酸4,5−エチレンジオキシ−
2−ニトロフエニルを得た(m.p.105〜106℃)。
これを80mlのメタノールに加熱溶解させた後、50
%水酸化ナトリウム水溶液4.0mlを滴下し、40〜
60℃に保つて1時間撹拌した。反応液を氷水で冷
却し、10%塩酸を加えて中和し、メタノールを留
去した後、析出した結晶を集、水洗、乾燥して
4,5−エチレンジオキシフエニル−2−ニトロ
フエノール4.50gを得た。
m.p. 173〜174℃ 収率74.8%
参考例 1
3,4−エチレンジオキシフエニルメチルケト
ン(6.00g、33.7mmol)とm−クロロ過安息香
酸(9.0g、52mmol)とを塩化メチレン200ml中、
室温下で3時間撹拌した。反応終了後、チオ硫酸
ナトリウム水溶液と炭酸水素ナトリウム水溶液と
で洗浄し、硫酸マグネシウムで乾燥し、塩化メチ
レンを留去した。酢酸3,4−エチレンジオキシ
フエニル5.93gを得た。収率90.7%
参考例 2
4,5−エチレンジオキシ−2−ニトロフエノ
ール(1.97g、10mmol)をアセトニトリル100ml
に溶かし、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℃に保つて30
分撹拌した。これにO−エチル N−sec−ブチ
ルチオノリン酸アミドクロリド(2.2g、
10mmol)を40分で滴下し、さらに3時間撹拌還
流した。放冷後、無機塩を別して、アセトニト
リルを留去し、残分をトルエンに溶かし、希塩
酸、水、希アルカリ水溶液、次いで水で洗浄し、
無水硫酸マグネシウムで乾燥した。トルエンを留
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−ブチ
ルホスホロアミドチオエート2.33gを得た。
m.p. 59〜61℃ 収率62.0%
参考試験例
ブドウべと病防除試験(治療効果)
プラスチツクポツトに砂壌土を詰め、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
苗にブドウべ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日間育成し、防除効力を調査
した。なお、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。
また、比較対照にクロロタロニールおよびトリ
(エチルホスホン酸)アルミニウムを用いた。そ
の結果を第1表に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 4,5-ethylenedioxy-2-nitrophenol and a method for producing the same. The compound of the present invention is an intermediate for the active ingredient of a plant disease control agent. That is, O-ethyl O-4,5-ethylenedioxy-2-nitrophenyl N- which can be produced by reacting the compound of the present invention with, for example, O-ethyl N-sec-butyl thionolamide chloride. sec-Butyl phosphoroamide thioate is an active ingredient of a plant disease control agent, and has a control effect against plant diseases such as downy mildew and late blight. The inventors have discovered that 4,5-ethylenedioxy-2
- As a result of studying the method for producing nitrophenol, it was found that 4,5-ethylenedioxy-2-nitrophenol can be produced in high yield and with high purity by nitrating and hydrolyzing 3,4-ethylenedioxyphenyl acetate. It has been discovered that phenol can be produced. Next, the method for producing the compound of the present invention will be described in detail. Nitration of 3,4-ethylenedioxyphenyl acetate is carried out using, for example, a mixed acid of sulfuric acid and nitric acid, a mixed acid of acetic acid and nitric acid, fuming nitric acid, or nitric acid in a halogenated hydrocarbon solvent, usually at 0 to 10°C, at 12 The reaction takes place within hours. After the reaction is completed, acetic acid 4,5
-ethylenedioxy-2-nitrophenyl is obtained. The hydrolysis of 4,5-ethylenedioxy-2-nitrophenyl acetate obtained as described above is as follows:
It is carried out in the presence of an alkali or acid catalyst. For hydrolysis with an alkali catalyst, for example, an alkaline aqueous solution such as sodium hydroxide is added to an alcoholic solution of 4,5-ethylenedioxy-2-nitrophenyl acetate, and the mixture is reacted at 40 to 60°C for 1 to 5 hours. Alternatively, 4,5-ethylenedioxy-2-nitrophenyl acetate is added to an alcoholate solution and the mixture is heated under reflux for usually 1 to 7 hours. Acid-catalyzed hydrolysis can be carried out using, for example, acetic acid 4,5
Hydrochloric acid or sulfuric acid is added as a catalyst to an alcoholic solution of -diethylenedioxy-2-nitrophenyl, and the reaction is usually carried out at 60 to 80°C for 4 to 8 hours. After the reaction is complete, the reaction mixture is neutralized, and if necessary, the solvent is distilled off, the resulting crystals are collected, washed with water, and then dried to obtain 4,5-ethylenedioxy-2-nitrophenol. 3,4-ethylenedioxyphenyl acetate, which is a raw material compound, is produced by reacting 3,4-ethylenedioxyphenyl methyl ketone with a peracid such as peracetic acid or metachloroperbenzoic acid, or by reacting 3,4-ethylenedioxyphenyl methyl ketone with a peracid such as peracetic acid or metachloroperbenzoic acid. It can be produced by reacting dioxyphenol with an acetylating agent such as acetic anhydride or acetyl chloride. In addition, 3,4-ethylenedioxyphenylmethylketone and 3,4-ethylenedioxyphenol are described in J.Chem.Soc., 1957 3445
It can be produced by the method described in 3447. Example 3,4-ethylenedioxyphenyl acetate (5.93
g, 30.5 mmol) in 15 ml of acetic acid and heated at 4-7°C.
A mixed solution of 2.0 ml of nitric acid (d=1.50) and 3.0 ml of acetic acid was added dropwise over 30 minutes while stirring. After the dropwise addition was completed, the temperature was returned to room temperature, the reaction solution was poured into ice water, the crystals were collected, washed with water, and acetic acid 4,5-ethylenedioxy-
2-nitrophenyl was obtained (mp 105-106°C).
After heating and dissolving this in 80ml of methanol, 50ml
Drop 4.0ml of % sodium hydroxide aqueous solution and add 40~
The mixture was kept at 60°C and stirred for 1 hour. The reaction solution was cooled with ice water, neutralized by adding 10% hydrochloric acid, and methanol was distilled off. The precipitated crystals were collected, washed with water, and dried to obtain 4,5-ethylenedioxyphenyl-2-nitrophenol. Obtained 4.50g. mp 173-174℃ Yield 74.8% Reference Example 1 3,4-ethylenedioxyphenylmethylketone (6.00g, 33.7mmol) and m-chloroperbenzoic acid (9.0g, 52mmol) were dissolved in 200ml of methylene chloride.
The mixture was stirred at room temperature for 3 hours. After the reaction was completed, the mixture was washed with an aqueous sodium thiosulfate solution and an aqueous sodium bicarbonate solution, dried over magnesium sulfate, and methylene chloride was distilled off. 5.93 g of 3,4-ethylenedioxyphenyl acetate was obtained. Yield 90.7% Reference Example 2 4,5-ethylenedioxy-2-nitrophenol (1.97 g, 10 mmol) was dissolved in 100 ml of acetonitrile.
Add anhydrous potassium carbonate powder (1.40g) and cuprous chloride (10mg), and keep at 40-50℃ for 30 minutes.
Stir for 1 minute. To this was added O-ethyl N-sec-butylthionolamide chloride (2.2 g,
10 mmol) was added dropwise over 40 minutes, and the mixture was further stirred and refluxed for 3 hours. After cooling, inorganic salts were separated, acetonitrile was distilled off, the residue was dissolved in toluene, and washed with dilute hydrochloric acid, water, dilute aqueous alkali solution, and then water.
It was dried with anhydrous magnesium sulfate. Toluene was distilled off, 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-butylphosphoroamide thioate. mp 59-61℃ Yield 62.0% Reference test example Grape mildew control test (therapeutic effect) Plastic pots were filled with sandy loam, grapes (neomuscatus seeds) were sown, and grown in a greenhouse for 50 days. A spore suspension of grape downy mildew was inoculated by spraying onto young grape seedlings in which the 4th to 5th true leaves had developed. After inoculation, the plants were grown for one 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, they were grown in a greenhouse at 23°C for 10 days, and their control 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", 10%. ``4'' if approved to a certain degree, ``3'' if approved by 30%, ``2'' if approved by 50%,
If it is observed in about 70%, it is scored as "1", and if it is more than 70% and there is no difference from the disease onset state when no compound is tested, it is scored as "0". , 3, 4, and 5. In addition, chlorothalonil and aluminum tri(ethylphosphonate) were used for comparison. The results are shown in Table 1. 【table】
Claims (1)
ノール。 2 酢酸3,4−エチレンジオキシフエニルをニ
トロ化した後、加水分解することを特徴とする
4,5−エチレンジオキシ−2−ニトロフエノー
ルの製造法。[Claims] 1 4,5-ethylenedioxy-2-nitrophenol. 2. A method for producing 4,5-ethylenedioxy-2-nitrophenol, which comprises nitrating 3,4-ethylenedioxyphenyl acetate and then hydrolyzing it.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14843583A JPS6041671A (en) | 1983-08-12 | 1983-08-12 | 4,5-ethylenedioxy-2-nitrophenol and its preparation |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14843583A JPS6041671A (en) | 1983-08-12 | 1983-08-12 | 4,5-ethylenedioxy-2-nitrophenol and its preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6041671A JPS6041671A (en) | 1985-03-05 |
JPH0439465B2 true JPH0439465B2 (en) | 1992-06-29 |
Family
ID=15452724
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14843583A Granted JPS6041671A (en) | 1983-08-12 | 1983-08-12 | 4,5-ethylenedioxy-2-nitrophenol and its preparation |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6041671A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106496061B (en) * | 2016-10-20 | 2018-06-05 | 湘潭大学 | A kind of method of acetyl spermine in extract and separate acylation reaction liquid |
-
1983
- 1983-08-12 JP JP14843583A patent/JPS6041671A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6041671A (en) | 1985-03-05 |
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