JPH0439466B2 - - Google Patents
Info
- Publication number
- JPH0439466B2 JPH0439466B2 JP15617983A JP15617983A JPH0439466B2 JP H0439466 B2 JPH0439466 B2 JP H0439466B2 JP 15617983 A JP15617983 A JP 15617983A JP 15617983 A JP15617983 A JP 15617983A JP H0439466 B2 JPH0439466 B2 JP H0439466B2
- Authority
- JP
- Japan
- Prior art keywords
- ethylenedioxy
- nitrophenol
- ethylenedioxynitrobenzene
- ethyl
- alkali metal
- 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 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- -1 ethylenedioxy-2-nitrophenol Chemical compound 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 150000001875 compounds Chemical class 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000233679 Peronosporaceae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XDHJIJSXCHOQQI-UHFFFAOYSA-N 5-nitro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=C1C=CC=C2[N+](=O)[O-] XDHJIJSXCHOQQI-UHFFFAOYSA-N 0.000 description 1
- CHSUFMWHKPBFBY-UHFFFAOYSA-N 6-chloro-7-nitro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=C1C=C([N+](=O)[O-])C(Cl)=C2 CHSUFMWHKPBFBY-UHFFFAOYSA-N 0.000 description 1
- MQSGCURTKWHBRX-UHFFFAOYSA-N 6-nitro-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC([N+](=O)[O-])=CC=C21 MQSGCURTKWHBRX-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
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- DSRXQXXHDIAVJT-UHFFFAOYSA-N acetonitrile;n,n-dimethylformamide Chemical compound CC#N.CN(C)C=O DSRXQXXHDIAVJT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides 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
- 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
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 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、一般式〔〕
〔式中、Xはハロゲン原子を表わす。〕
で示される2−ハロ−4,5−エチレンジオキシ
ニトロベンゼンを溶媒中、アルカリ金属水酸化物
の存在下に反応させることによる4,5−エチレ
ンジオキシ−2−ニトロフエノールの製造法に関
する。
4,5−エチレンジオキシ−2−ニトロフエノ
ールは植物病害防除剤の有効成分の中間体であ
る。すなわち、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−ブチ
ル チオ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、上記一般式〔〕で示される2−ハロー4,
5−エチレンジオキシニトロベンゼンを、溶媒
中、2当量以上のアルカリ金属水酸化物の存在下
で、1時間から24時間程度、70〜200℃に加熱す
ることによつて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
見い出した。
上述の製造法において、溶媒としては、例えば
ジオキサン、テトラヒドロフラン、エチレングリ
コールジメチルエーテル等のエーテル、アセトニ
トリル、イソブチロニトリル等のニトリル、N,
N−ジメチルホルムアミド、N,N−ジメチルア
セトアミド等の酸アミド、ジメチルスルホキシ
ド、スルホラン等の硫酸化合物が挙げられる。
アルカリ金属水酸化物としては、例えば水酸化
ナトリウム、水酸化カリウムが挙げられる。
反応終了後は通常の後処理を行ない、必要なら
ば、クロマトグラフイー、再結晶等によつて精製
する。
原料化合物である一般式〔〕で示される2−
ハロ−4,5−エチレンジオキシニトロベンゼン
は、例えば一般式〔〕
〔式中、Xは前記と同一の意味を表わし、Yは
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)エタノールを前記のアルカリ金属水酸
化物またはフツ化カリウム、フツ化セシウム等の
フツ化物の存在下、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、スル
ホラン等の溶媒中、加熱することによつて製造す
ることができる。
次に、実施例を示す。
実施例 1
2−クロロ−4,5−エチレンジオキシニトロ
ベンゼン500mgをジメチルスルホキシド5mlに溶
かし、100℃に加熱して水酸化カリウム粉末400mg
を加え、120〜140℃に1時間保つた。冷却後、氷
水50ml中に注ぎ、酢酸エチル50mlを用いて2度抽
出し、抽出液を水洗後、硫酸マグネシウムで乾燥
した。酢酸エチルを留去し、残分をシリカゲルカ
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290mgを得
た。
m.p.170〜173℃
実施例 2
2−フルオロ−4,5−エチレンジオキシニト
ロベンゼン2.6gをスルホラン15mlに溶かし、水
酸化カリウム粉末2.2gを加えて80〜100℃に3時
間保つた。冷却後、氷水100mlに注ぎ、実施例1
と同様に処理して、4,5−エチレンジオキシ−
2−ニトロフエノール1.38g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
−ブチル 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
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
100mlに溶かし、これに無水炭酸カリウム(1.40
g)と塩化第一銅(10mg)とを加えて40〜50℃で
30分撹拌した。ついでO−エチル N−sec−ブ
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時間撹拌還流し
た。無機塩を別した後、アセトニトリルを減圧
留去した。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−ブチ
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
ブドウべと病防除効果試験(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。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。
【表】[Detailed Description of the Invention] The present invention relates to the general formula [] [In the formula, X represents a halogen atom. ] It is related with the manufacturing method of 4,5-ethylenedioxy-2-nitrophenol by reacting 2-halo-4,5-ethylenedioxynitrobenzene shown by these in a solvent in the presence of an alkali metal hydroxide. 4,5-ethylenedioxy-2-nitrophenol is an intermediate of the active ingredient of a plant disease control agent. That is, 4,5-ethylenedioxy-2-
O-ethyl O- which can be produced by reacting nitrophenol with O-ethyl N-sec-butyl thiophosphoamide chloride
4,5-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. The present inventors obtained 4,5-ethylenedioxy-2-
As a result of studying the method for producing nitrophenol, we found that 2-halo 4, represented by the general formula [] above,
5-ethylenedioxynitrobenzene is heated to 70 to 200°C for about 1 to 24 hours in a solvent in the presence of 2 equivalents or more of alkali metal hydroxide to produce 4,5-ethylenedioxynitrobenzene. -2-
It has been discovered that nitrophenol can be produced. In the above production method, examples of solvents include dioxane, tetrahydrofuran, ethers such as ethylene glycol dimethyl ether, nitriles such as acetonitrile and isobutyronitrile, N,
Examples include acid amides such as N-dimethylformamide and N,N-dimethylacetamide, and sulfuric acid compounds such as dimethyl sulfoxide and sulfolane. Examples of alkali metal hydroxides include sodium hydroxide and potassium hydroxide. After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, recrystallization, etc. 2- represented by the general formula [] which is a raw material compound
Halo-4,5-ethylenedioxynitrobenzene has the general formula [] [In the formula, X represents the same meaning as above, and Y represents a halogen atom. ] β-(2,4-dihalo-5-nitrophenoxy)ethanol represented by the above is mixed with acetonitrile N,N-dimethylformamide, in the presence of the alkali metal hydroxide or fluoride such as potassium fluoride or cesium fluoride It can be produced by heating in a solvent such as dimethyl sulfoxide or sulfolane. Next, examples will be shown. Example 1 500 mg of 2-chloro-4,5-ethylenedioxynitrobenzene was dissolved in 5 ml of dimethyl sulfoxide, heated to 100°C, and 400 mg of potassium hydroxide powder was dissolved.
was added and kept at 120-140°C for 1 hour. After cooling, the mixture was poured into 50 ml of ice water, extracted twice with 50 ml of ethyl acetate, and the extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off, and the residue was purified by silica gel column chromatography to obtain 290 mg of 4,5-ethylenedioxy-2-nitrophenol. mp170-173°C Example 2 2.6 g of 2-fluoro-4,5-ethylenedioxynitrobenzene was dissolved in 15 ml of sulfolane, 2.2 g of potassium hydroxide powder was added, and the mixture was kept at 80-100°C for 3 hours. After cooling, pour into 100ml of ice water, Example 1
4,5-ethylenedioxy-
1.38 g of 2-nitrophenol was obtained. 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 4,5-ethylenedioxy-2-nitrophenol (1.97 g, 10 mmol) was dissolved in acetonitrile.
Dissolve in 100ml and add anhydrous potassium carbonate (1.40
g) and cuprous chloride (10 mg) at 40-50℃.
Stirred for 30 minutes. Then, O-ethyl N-sec-butylthionolamide chloride (2.2 g, 10 mmol) was added dropwise over 40 minutes, followed by stirring and refluxing for 3 hours. After separating the inorganic salts, acetonitrile was distilled off under reduced pressure. 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 phosphoramidothioate. mp59-61℃ Reference test example Grape mildew control effect 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, the plants were grown in a greenhouse at 23°C for 10 days, and their control efficacy was investigated. The pesticidal efficacy is evaluated 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 more than that. If there is no difference from the disease onset state, it is evaluated as "0" and evaluated on a 6-level scale from 0 to 5.
Displayed as 1, 2, 3, 4, 5. In addition, chlorothalonil and aluminum tris(ethylphosphonate) were used as comparison controls. The results are shown in Table 2. [Table]
Claims (1)
ニトロベンゼンを溶媒中、アルカリ金属水酸化物
の存在下に反応させ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. General formula [In the formula, X represents a halogen atom. ] 2-halo-4,5-ethylenedioxynitrobenzene represented by is reacted in a solvent in the presence of an alkali metal hydroxide.
A method for producing ethylenedioxy-2-nitrophenol.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15617983A JPS6048984A (en) | 1983-08-25 | 1983-08-25 | Production of 4,5-ethylenedioxy-2-nitrophenol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15617983A JPS6048984A (en) | 1983-08-25 | 1983-08-25 | Production of 4,5-ethylenedioxy-2-nitrophenol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6048984A JPS6048984A (en) | 1985-03-16 |
JPH0439466B2 true JPH0439466B2 (en) | 1992-06-29 |
Family
ID=15622078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP15617983A Granted JPS6048984A (en) | 1983-08-25 | 1983-08-25 | Production of 4,5-ethylenedioxy-2-nitrophenol |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6048984A (en) |
-
1983
- 1983-08-25 JP JP15617983A patent/JPS6048984A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6048984A (en) | 1985-03-16 |
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