JPS5879961A - O-fluoroaniline derivative and its preparation - Google Patents

O-fluoroaniline derivative and its preparation

Info

Publication number
JPS5879961A
JPS5879961A JP56180046A JP18004681A JPS5879961A JP S5879961 A JPS5879961 A JP S5879961A JP 56180046 A JP56180046 A JP 56180046A JP 18004681 A JP18004681 A JP 18004681A JP S5879961 A JPS5879961 A JP S5879961A
Authority
JP
Japan
Prior art keywords
general formula
fluoro
derivative
chloro
water
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
Application number
JP56180046A
Other languages
Japanese (ja)
Other versions
JPH0251894B2 (en
Inventor
Hideyoshi Nagano
栄喜 永野
Shunichi Hashimoto
俊一 橋本
Akira Yoshida
亮 吉田
Keiji Matsumoto
啓志 松本
Katsuzo Kamoshita
鴨下　克三
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP56180046A priority Critical patent/JPS5879961A/en
Priority to US06/360,999 priority patent/US4484941A/en
Priority to US06/360,997 priority patent/US4484940A/en
Priority to AU81930/82A priority patent/AU550845B2/en
Priority to DK140382A priority patent/DK154212C/en
Priority to DE8282102565T priority patent/DE3266288D1/en
Priority to EP82102565A priority patent/EP0061741B1/en
Priority to ES510917A priority patent/ES8305713A1/en
Priority to CA000399595A priority patent/CA1164002A/en
Priority to AR28891182A priority patent/AR230424A1/en
Priority to CA000399608A priority patent/CA1164467A/en
Priority to MX793482A priority patent/MX155119A/en
Priority to BG5602082A priority patent/BG40644A3/en
Priority to PL23570882A priority patent/PL133782B1/en
Priority to BR8201807A priority patent/BR8201807A/en
Publication of JPS5879961A publication Critical patent/JPS5879961A/en
Priority to CA000428781A priority patent/CA1186337A/en
Priority to CA000429249A priority patent/CA1186338A/en
Priority to US06/651,877 priority patent/US5030760A/en
Priority to US06/903,830 priority patent/US4736068A/en
Priority to DK591387A priority patent/DK159845C/en
Priority to US07/130,522 priority patent/US4835324A/en
Priority to MY8800096A priority patent/MY8800096A/en
Priority to DK142990A priority patent/DK163818C/en
Priority to DK143090A priority patent/DK160487C/en
Publication of JPH0251894B2 publication Critical patent/JPH0251894B2/ja
Priority to US07/650,943 priority patent/US5191105A/en
Granted legal-status Critical Current

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Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Abstract

NEW MATERIAL:A compound of formulaI(X is Cl, Br; R is alkyl). EXAMPLE:4-Chloro-2-fluoro-5-isopropoxyphenylaniline. USE:A synthetic intermediate of N-phenyltetrahydrophthalimide derivative, which is used as a herbicide. PREPARATION:The catalytic hydrogenation of o-fluoronitrobenzene derivative is effected in the presence of platinum dioxide in a solvent such as ethanol at room temperature and normal pressure to give the compound of formulaI. This reaction is also conducted by a usual method of converting an aromatic nitro group into an amino group, such as with sodium sulfide or iron dust or catalytic hydrogenation.

Description

【発明の詳細な説明】 本発明は、一般式（ｉｌ ｉｔｏ　　　　。[Detailed description of the invention] The present invention is based on the general formula (il ito.

（式中、Ｘは塩素原子または臭素原子を、凡はアルキル
基金表わす。） で示されるＮ−フェニルテトラヒドロフタルイミド誘導
体の重要合成中間体である一般式（ＴＩ）Ｆ ｉＯ （式中、ＸおよびＲＨ前述のとおりである。）で示され
るアニリン誘導体およびその製造法にレフタルイミド９
ｉ４体は、トウモロコシ、コムギ、り゛イズ、イネ、ワ
タ等の重要作物に杏の少ない、非常に強力な殺草力を有
するものである代表的なものとしては、Ｎ−（４−クロ
ロ−２＝フルオロ−５−イソブロホキシフエニｆｉ／）
　−５，６，７，８−テトラヒドロフタルイミドケあけ
ることができる。その除草力の一例才以十に簡単ＶＣ説
明する。(In the formula, X represents a chlorine atom or a bromine atom, and generally represents an alkyl group.) As mentioned above, phthalimide 9 is added to the aniline derivative shown in
i4 has a very strong herbicidal effect on important crops such as corn, wheat, wheat, rice, and cotton.A typical example is N-(4-chloro- 2=Fluoro-5-isobroxyphenifi/)
-5,6,7,8-tetrahydrophthalimide. I will give a simple explanation of VC's weeding power as an example.

除草剤としての以下の試験例において栽培種、１′ 物に対する薬害と雑草に対する効力との評価はすべて以
下に述べる基準にしたかい、０から５１での整数による
評価（ｉＮｉで表わした。調査時点に枯れ残つｆｃ、植
物体の地上′１″１１への牛Ｍ１１計をはかり、無処理
区の植物体の生沖土１と比較したときの比率（％）を割
算する。栽培植物と雑草について下表のような基準にも
とづき、薬害と除草効力會０から５’！’での数字で評
価した。栽培植物に対する評価値０またはｌあるいは頼
草に対する評価値５または４は一般に妥当な栽培植物保
護効果、あるいは雑草防除効果とみなされる。In the following test examples as herbicides, evaluations of phytotoxicity against cultivated species, 1' substances, and efficacy against weeds were all based on the criteria described below. Measure the total amount of fc that remains withered and cattle M11 to the ground level of the plant body, and divide the ratio (%) when compared with the fresh soil of the plant body in the untreated area. Weeds were evaluated based on the criteria shown in the table below, using numerical values from 0 to 5'!' for chemical damage and herbicidal efficacy.An evaluation value of 0 or 1 for cultivated plants or an evaluation value of 5 or 4 for grasses is generally appropriate. It is considered to have a protective effect on cultivated plants or a weed control effect.

なお、水稲試験の場合のみ、植物体の乾燥重量により評
価値ケ算出している３゜ 参考しｌｊ　　）ウモＬｌコシ除草試験（茎葉処理）た
て３５ｃＩ＋＋、よこ２５ａ、１ｃかさｌＱｃ＋＋＋の
フ゛ラスチックトレーに畑地土壊紮詰め、トウモロコシ
、イチビ、ヒマワリ、エヒスグサ、マルバアザガＡ１ノ
ハッカラシ、ハコベおよびエノコ「ｌグサ旨捕〜し、温
室内で２過間育成したあと、たて５０σ、よこ１００Ｇ
、たかさ４０（ｆｉ＋の枠内にこのトレーを２個運べ、
植物体の−Ｌ方から小型噴霧器で各薬剤の所定量を枠内
全面に：８葉処理した。薬剤散布後さらに３週間温室内
で′＾成したあと、各植物ごとに薬害あるいは除草効力
をＦＡ貴し７た。その結果を第１表にホす１．なお処理
薬沖」は乳刑葡使用し、ｋ　＊　Ｍ　’ｒ：加えた水に
乳化させたものを供試した。桑剤処理時の植物の大きさ
は種類によって異なるが、はぼ木葉１〜３葉期で草丈２
〜２０口であった。In addition, only in the case of the paddy rice test, the evaluation value is calculated based on the dry weight of the plant. Filled with soil in the field, harvested corn, crocodile, sunflower, scallion, A1 red mustard, chickweed, and hackberry.
, height 40 (carry 2 of these trays within the fi+ frame,
A predetermined amount of each chemical was applied from the -L side of the plant using a small sprayer to the entire area within the frame: 8 leaves. After the plants were grown in the greenhouse for an additional three weeks after the chemical spraying, each plant was subjected to FA testing for phytotoxicity or herbicidal efficacy. The results are shown in Table 1.1. Incidentally, the processing drug Oki was prepared by using daikon grapes and emulsifying it in water with k*M'r added. The size of the plant when treated with mulberry agent varies depending on the species, but the plant height is 2 at the 1-3 leaf stage.
It was ~20 mouths.

（５） 第　　１　　衣 ↑ ★ ※アトラジン （ン ？ この一般式（Ｉ）で示される除４　Ｍ’ｌとして有用な
化合物は、次の反応式で示さＪ′しる様に、−（６） 般式Ｍのフェノール誘導体より一般式（′［Ｄで示され
る本発明化合物を経由して合成される。(5) No. 1 ↑ ★ *Atrazine (N?) Compounds useful as 4 M'l shown in this general formula (I) are -(6) as shown in the following reaction formula. It is synthesized from a phenol derivative of the general formula M via the compound of the present invention represented by the general formula ('[D).

（ｖ）　　　　　　　（Ｉｖ）　　　　　　　　０ｕ）
（式中、ＸおよびＲＦＸ、前述のとおりである）一般式
（ＩＴＪで示されるアニリン誘導体は、３゜４．５．６
−チトラヒドロフタ）ｖｈ無水物と酢酸の様な不油性な
溶媒あ存在下あるいは無溶媒で５０〜１５０℃、好まし
くは酢酸還流程度の温度で１〜６時間、好ましくは２〜
４時間反応させることで、一般式（Ｉ）で示されるＮフ
ェニルテトラヒドロフタルイミド誘導体に変換される。(v) (Iv) 0u)
(wherein, X and RFX are as described above) The aniline derivative represented by the general formula (ITJ) is
-titrahydrophtha) vh anhydride and an oil-free solvent such as acetic acid or no solvent at 50 to 150°C, preferably at a temperature of about refluxing acetic acid for 1 to 6 hours, preferably 2 to 6 hours.
By reacting for 4 hours, it is converted into an N-phenyltetrahydrophthalimide derivative represented by general formula (I).

一般式（１１）で示されるアニリン誘導体は、通常、芳
香ｒｔ；＋−ｔ′、のニトロ基のアミノ基への還元に用
いられる方法、たとえば硫化ナトリウム、鉄粉、接触織
元等いずれの方法でも一般式（］■）で示されるニトロ
ベンゼン誘導体より合成することが口Ｈｉｔ：であるが
、エタノールを溶媒とし、１酸１ヒ白金を触媒とした常
温、常圧の接触ムシ元が好ましい、原料となる一般式（
ｉｌｌ　）で示されるニトロベンゼン誘導体は一般式（
ｉｖ　）で示されるニトロフェノ−）Ｖ誘導体のエーテ
ル化で合成される。詳した後、ジメチルホルムアミド、
アセトニトリル、アセトン、ジメチルスルホキシド等の
極性溶妨の存在下、１０〜２００℃、好着しくは８０〜
１００℃でアルキルハライドと反応させることにより行
なわれる。The aniline derivative represented by the general formula (11) can be obtained by any method used for reducing the nitro group of the aromatic rt; Synthesis from the nitrobenzene derivative represented by the general formula (]■) is a good idea, but it is preferable to use a contact base at room temperature and pressure using ethanol as a solvent and platinum monoacid as a catalyst. The general formula (
The nitrobenzene derivative represented by ill) has the general formula (
It is synthesized by etherification of the nitropheno-)V derivative shown in iv). After detailed explanation, dimethylformamide,
10-200°C, preferably 80-200°C in the presence of a polar dissolving agent such as acetonitrile, acetone, dimethylsulfoxide, etc.
This is carried out by reacting with an alkyl halide at 100°C.

一般式（ＩＶ）のニトロフェノ−／ｌ／　誘導体ｒ、ｒ
、一般式（Ｖ）のハローフェノールより次式に従っで合
成される１、 Ｐ　　　　　　　Ｉ　　　　　　Ｆ （Ｖ）　　　　　　（ＶＩ）　　　　　　（■）ｔ′ （式中、Ｘは前述のとおりである。） 一般式〜）で示されるフェノ−／ｖＥｌｌ　与体ｔ」、
０、Ｏ，Ｆｉｎｇｅｒ　　ら、Ｊ、Ａｍ、０ｈｅＦ、８
ｏｓ、　８１９４（１９５９）で公知である。Nitropheno-/l/ derivatives r, r of general formula (IV)
, 1 synthesized from halophenol of general formula (V) according to the following formula, P I F (V) (VI) (■)t' (wherein, X is as described above) General formula ~ ),
0,O,Finger et al.,J,Am,0heF,8
os, 8194 (1959).

一般式（Ｖｌで示されるフェノ−／Ｌ／誘導体を水イし 酸化すｌ・リウム、水１ｒＴリウム等の水ｌ谷液でアル
カリ金属塩とした後、クロルギ酸メチルと水溶媒下、好
１しくは（）〜】０℃で反応させることで一般式（ＶＴ
）で示される戻酸ニスデル誘尋体を得ることができる１
、さらに濃硫酸、濃硝酸音用いたニトロ化を常温で行な
うことにより一般式（Ｖｌｌ）で示されるニトロベンゼ
ン誘導体＋−ｉ＝することかできる。このニトロベンゼ
ン誘導体は、水酸化ナトリウム等のアルカリ水溶液を用
いて、好１しくに４０〜８０℃で加水分解を行なうこと
により一般式（ＩＶ）で示されるニトロフェノ−／し誘
Ｗ（本に変換される。この選択的二１ロ化ｒ１多くのク
ロル蟻酊エステル類を用いても、ｌ−６Ｉｆ、同様の結
果を得ることが可ｎニである。A phenol/L/derivative represented by the general formula (Vl) is made into an alkali metal salt by diluting with water such as sulfur oxide, 1rTtrium, etc., and then treated with methyl chloroformate in an aqueous solvent. Or ()~]By reacting at 0℃, the general formula (VT
) can be obtained as 1
Further, by carrying out nitration using concentrated sulfuric acid and concentrated nitric acid at room temperature, a nitrobenzene derivative +-i= represented by the general formula (Vll) can be obtained. This nitrobenzene derivative can be converted into a nitrophenol/silane W (converted to nitrite) represented by the general formula (IV) by hydrolysis using an alkaline aqueous solution such as sodium hydroxide, preferably at 40 to 80°C. It is possible to obtain similar results even if many chloride esters are used in this selective 2-1 conversion.

次に実施例ケ示し、より訃細な油、明を行なう。Next, examples will be shown, and more refined oils and brightness will be shown.

実施例１ ４−クロロ−２−フルオロ−５−４ソプロボキシフエニ
ルアニリン ４−クロロ−２−フルオロ−５−（ラフ９０ボキシニト
ロベンセンＩＢ、５ｔ＃：エタノールを吸収した時点で
不溶物をｒ別、ｒ成金濃縮し、残渣をシリカケルクロマ
トクラフィーによ勺ＭＩＪし、５．６１の４−クロロ−
２−フルオロ−５−イソプロホキジフェニルアニリン全
役た１、　　７ＬＤ１．５８６０ 全く同様にして第２衣の化合物を合成した。Example 1 4-chloro-2-fluoro-5-4soproboxyphenylaniline 4-chloro-2-fluoro-5-(rough 90 boxynitrobenzene IB, 5t#: insoluble matter upon absorption of ethanol) was separated, concentrated, and the residue was subjected to silica gel chromatography using MIJ to obtain 5.61 4-chloro-
2-Fluoro-5-isoprophoxydiphenylaniline 1,7LD1.5860 A second compound was synthesized in exactly the same manner.

参考例１ ４−クロロ−２−フル：Ａ−ｔ」−５−４ソブロポキシ
ニトロベンセン ２−クロロ−４−フルオロ−５−ニトロフル　）　−　
ル　　　　１９、１１１サ　ア−ａｌ−ニ　ト　リ　ル
　１００−に溶かし、無水炭酸カリウム８９ヲ加え、室
温で数分攪拌した後、ヨウ化イソプロピル２５９−を加
え、３時間還流した。放冷後、水を加えエーテルで抽出
した。抽出液を５％水酸化ナトリウム水溶液、水で洗い
、無水硫酸マグネシウムで乾燥した。乾燥剤全炉別し、
ｒ液を減圧で濃縮した。残渣は水冷下結晶しエタノール
より再結晶して、１８．５５’の４−クロロ−２−フル
オロ−５−イソフーロボキシニトロベンセ′ンヲ得た。Reference Example 1 4-chloro-2-fur:A-5-4sobropoxynitrobenzene 2-chloro-4-fluoro-5-nitroflu) -
89% of anhydrous potassium carbonate was added to the mixture, and after stirring at room temperature for several minutes, 259% of isopropyl iodide was added and the mixture was refluxed for 3 hours. After cooling, water was added and extracted with ether. The extract was washed with a 5% aqueous sodium hydroxide solution and water, and dried over anhydrous magnesium sulfate. All desiccant furnaces are separated,
The r solution was concentrated under reduced pressure. The residue was crystallized under water cooling and recrystallized from ethanol to obtain 18.55' 4-chloro-2-fluoro-5-isofluorboxynitrobenzene.

ｍｐ　６１．８〜６２４℃ＮＭＲ８（ｐｐｍ）　ＣＤＣ
ｆａ　　１．４２　（６Ｈ，ｄ　。mp 61.8-624℃ NMR8 (ppm) CDC
fa 1.42 (6H, d.

Ｊ＝７Ｒ７）、４１〜４．８　（ｌ　）ｌ　、　ｍ　）
、７．２８　（ＩＩ（、ｄ　、　Ｊ＝　Ｉ　Ｑｕｚ　）
、　７．４８（ｔＨ，ｄ　、　Ｊ　＝（ｉ）ｌｚ　）参
考例２ ２−クロロ−４−フルオロ−５−ニトロフル　ノ　−　
ル ２−クロロ−４−フルオロフェノ−）Ｖ　８８．４１を
水酸化ナトリウム２７．７　Ｐおよび水４５〇−より調
整した水酸化ナトリウム水溶沿に加え、１０℃以下でメ
チルクロロホーメート６９．２１を滴下した。生じた結
晶を炉別、水洗して１８４．８５’の粗製のメチル　（
２−クロロ−４−フルオロフエニ）Ｖ）ホーメートヲ得
た。ｍｐ６９−７１”Ｃメｆ／ｌｚ　　（２−り０ロー
４−フルオロフエニ）ｖ　）ホーメート１８４．８５’
に濃硫酸５０　ｍｌにけん濁し、これに混酸（濃硫酸５
０ｍｅ、濃硝酸５０　ｍｅ　）を３０℃付近で滴下し、
さらに】時局その温度で撹拌した。反応液を氷にあけ、
生じた結晶は繰り返し水洗し、１４８Ｐのメチル　（２
−クロロ−４−フルオロ−５−ニトロフェノ）Ｖ）ホー
メートを得た。ｍｐ　５８〜５５℃　これ全水酸化ナト
リウム２７Ｐ、水８００　ｍｅと共に４時間還流した。J=7R7), 41-4.8 (l)l,m)
, 7.28 (II(, d, J= I Quz)
, 7.48 (tH, d, J = (i) lz) Reference example 2 2-chloro-4-fluoro-5-nitrofluno-
2-chloro-4-fluoropheno-)V 88.41 was added to an aqueous solution of sodium hydroxide prepared from 27.7 P of sodium hydroxide and 450 P of water, and methyl chloroformate 69.21 was dripped. The resulting crystals were separated from the furnace and washed with water to give 184.85' crude methyl (
2-chloro-4-fluorophene) V) formate was obtained. mp69-71"C f/lz (2-ri 0-low 4-fluorophene)v) homeate 184.85'
Suspend in 50 ml of concentrated sulfuric acid, add mixed acid (50 ml of concentrated sulfuric acid)
0me, concentrated nitric acid (50me) was added dropwise at around 30℃,
Furthermore, the mixture was stirred at that temperature. Pour the reaction solution on ice,
The resulting crystals were repeatedly washed with water and 148P methyl (2
-chloro-4-fluoro-5-nitropheno) V) formate was obtained. mp 58-55° C. This was refluxed for 4 hours with 27 P of total sodium hydroxide and 800 me of water.

生じた不削物はセライト沖過し、距液全濃塩酸で酸性と
して生じた結晶’ｋ　Ｐ　別、水洗し、２−クロロ−４
−フルオロ−５−ニトロフェノ−ｔＶＴ６．８９を得た
。The resulting uncut material was filtered through celite, and the resulting crystals were acidified with concentrated hydrochloric acid.
-Fluoro-5-nitropheno-tVT6.89 was obtained.

ｍｐ　１０６〜１０７−Ｃ Ｎ　Ｍ　Ｒ（０ＤＯ１！ａ、１）６−ＤＭ８０）　　δ
円曲　７．２５参考例３ ２−ブロモ−４−フルオロ−５−ニトロフル　ノ　−　
ル ２−ブロモー４−フルオロフェノール２８１を水酸化す
トリウム水的液（水酸化ナトリウム７　！ｉ’　ｋ　１
００　ｍｌの水に溶解したもの）　ｌ／Ｃ加え、１０°
０以下でクロル購酩メチルを７丙士し、生じた結晶はｐ
別、水洗し、４１ｙの２〜ブロモ−４−フルオロフコニ
ル蟻酸メチルを得た。ｎｉｐ　８０．７℃ これｆ：１８　ｍｅＯＶｌｌ！ＪｌｉＩＩＣｆｍｔに懸
濁し、濃硫酸１３−１濃硝酸ｌａｍｂの混−〉′を３０
℃付近で滴）した。さらＶＣ８０分指打し１氷にそそき
生じた結晶を艮く水洗し、３８３１の黄色結晶として２
−ブロモ−４−フルオロ−５−二トロ蟻酸　メ　チ　ル
　ｋＮｆｃ、　　　ｍｐ　　６　３．　５　〜６４５　
℃これを水酸化ナトリウム６２ｚ、水１００　ｍｅと共
に３時間還流し友。不俗物ヶ炉別し、戸数を塩酸”で酸
性とし、生じた結晶は戸別し水洗して２５　Ｐ　Ｑ）　
２−ブロモ−４−フルオロ−５−二トロフェノールｋｈ
ｆｃ、　ｘｎｐ　１２６〜１２７℃ Ｎ　Ｍ　Ｒ（ＣＤＣｌ！３　、　Ｉ）６−１）Ｍ２Ｏ）
　　δｐｐｍ７．４２（ＩＨ，ｔｉ、Ｊ＝ｌ　０ｌ−１
ｚ）（１５児）mp 106-107-C NMR (0DO1!a, 1)6-DM80) δ
Circular curve 7.25 Reference example 3 2-bromo-4-fluoro-5-nitrofluno-
Thorium aqueous solution (sodium hydroxide 7 !i' k 1
(dissolved in 00 ml of water) l/C added, 10°
The crystals produced by purchasing methyl chloride at a temperature below 0 are p
Separately, the mixture was washed with water to obtain 41y, methyl 2-bromo-4-fluorofuconyl formate. nip 80.7℃ This f:18 meOVll! Suspended in JliIIICfmt and mixed with concentrated sulfuric acid 13-1 concentrated nitric acid lamb for 30 minutes.
(drops at around ℃). Further, finger tap VC for 80 minutes. 1. Wash the crystals that formed on ice with water. 2. As yellow crystals of 3831.
-Methyl bromo-4-fluoro-5-ditroformate kNfc, mp 6 3. 5 ~ 645
℃ This was refluxed for 3 hours with 62ml of sodium hydroxide and 100ml of water. Separate the vulgar items into furnaces, acidify them with hydrochloric acid, and remove the crystals that form and wash them with water for 25 days.Q)
2-bromo-4-fluoro-5-nitrophenol kh
fc, xnp 126-127℃ NMR (CDCl!3, I)6-1)M2O)
δppm7.42 (IH, ti, J=l 0l-1
z) (15 children)

Claims (2)

【特許請求の範囲】[Claims] （１）一般式 （式中、Ｘは塩素原子または臭素原子ケ、■はアルキル
基金表わす。〕 で示すれる０−フルオロアニリン誘導体。(1) An 0-fluoroaniline derivative represented by the general formula (wherein, X represents a chlorine atom or a bromine atom, and ■ represents an alkyl group). （２）　　一般式 （） （式中、Ｘは塩素原子または臭素原子を、■はアルキル
基金表わす。） テ示すしるＯ−フルオロニトロベンゼン誘導体を選択的
に還元することを特徴とする一般式 （式中、Ｘ、１１は前述のとおりである。）で示される
０−フルオロアニリン誘ｉ体の製造法、。(2) General formula () (In the formula, X represents a chlorine atom or a bromine atom, and ■ represents an alkyl group.) General formula ( A method for producing an 0-fluoroaniline derivative i represented by the formula (wherein X and 11 are as described above).
JP56180046A 1981-03-30 1981-11-09 O-fluoroaniline derivative and its preparation Granted JPS5879961A (en)

Priority Applications (25)

Application Number Priority Date Filing Date Title
JP56180046A JPS5879961A (en) 1981-11-09 1981-11-09 O-fluoroaniline derivative and its preparation
US06/360,999 US4484941A (en) 1981-09-01 1982-03-23 Tetrahydrophthalimides, and their production and use as herbicides
US06/360,997 US4484940A (en) 1981-09-01 1982-03-23 Tetrahydrophthalimides, and their production and use as herbicides
AU81930/82A AU550845B2 (en) 1981-03-30 1982-03-25 Tetrahydrophthalimides and their starting compounds
DK140382A DK154212C (en) 1981-03-30 1982-03-26 TETRAHYDROPHTHALIMIDES, A HERBICID PREPARATION CONTAINING THESE, AND THEIR USE FOR THE FERTILIZATION OF WEEDS
DE8282102565T DE3266288D1 (en) 1981-03-30 1982-03-26 Tetrahydrophthalimides, and their production and use
EP82102565A EP0061741B1 (en) 1981-03-30 1982-03-26 Tetrahydrophthalimides, and their production and use
ES510917A ES8305713A1 (en) 1981-03-30 1982-03-29 Herbicidal N-di:halophenyl-tetra:hydro-phthalimide derivs.
CA000399595A CA1164002A (en) 1981-09-01 1982-03-29 Tetrahydrophthalimides, and their production and use
AR28891182A AR230424A1 (en) 1981-03-30 1982-03-29 NEW DERIVATIVES OF 2-FLUOR-4-CHLORINE OR 5-HYDROXY ANILINE NITROBENZENE PROCEDURE FOR PREPARING THEM; N- (2-FLUOR-HALO-5-PHENYL) 3,4,5,6-TETRAHYDROPHTHALIMIDES OBTAINED FROM THESE DERIVATIVES PROCEDURES FOR ITS PREPARATION
CA000399608A CA1164467A (en) 1981-09-01 1982-03-29 Tetrahydrophthalimides, and their production and use
BG5602082A BG40644A3 (en) 1981-03-30 1982-03-30 Herbicide means and method for protection from weeds
BR8201807A BR8201807A (en) 1981-03-30 1982-03-30 COMPOUND INTERMEDIATE COMPOUNDS FOR THE SAME PROCESSES FOR ITS RESPECTIVE PREPARATION HERBICIDE COMPOSITION PROCESS TO CONTROL WEEDS AND USE OF A COMPOUND
MX793482A MX155119A (en) 1981-03-30 1982-03-30 PROCEDURE FOR THE PREPARATION OF N- (2-FLUORO-4-HALO-5-PHENYL-SUBSTITUTED) -3,4,5,6-TETRA-HYDROPHTHALIMIDES
PL23570882A PL133782B1 (en) 1981-03-30 1982-03-30 Herbicide and process for preparing n-/4-halo-2-fluoro-5-substituted phenyl/-3,4,5,6-tetrahydrophtalimide
CA000428781A CA1186337A (en) 1981-09-01 1983-05-24 Intermediates for producing tetrahydrophthalimides
CA000429249A CA1186338A (en) 1981-09-01 1983-05-30 Starting materials for producing tetrahydrophthalimides
US06/651,877 US5030760A (en) 1981-09-01 1984-09-18 Tetrahydrophthalimides, and their production and use
US06/903,830 US4736068A (en) 1981-09-01 1986-09-03 Tetrahydrophthalimides and their production and use as herbicides
DK591387A DK159845C (en) 1981-03-30 1987-11-11 1-AMINO-2-FLUORO-4-HALOGENE BENZEN DERIVATIVES AND A PROCEDURE FOR PREPARING THEREOF
US07/130,522 US4835324A (en) 1981-09-01 1987-12-09 Tetrahydrophthalimides, and their production and use
MY8800096A MY8800096A (en) 1981-03-30 1988-12-30 Tetrahydro phthalimides and their production and use
DK142990A DK163818C (en) 1981-03-30 1990-06-11 4-FLUORO-2-HALOGEN-5-NITROPHENOLS AND A PROCEDURE FOR PREPARING THEREOF
DK143090A DK160487C (en) 1981-03-30 1990-06-11 N- (2-FLUORO-4-HALOGEN-5-HYDROXYPHENYL) -3,4,5,6-TETRAHYDROPHTHALIMIDE COMPOUNDS AND A PROCEDURE FOR PREPARING THEREOF
US07/650,943 US5191105A (en) 1981-09-01 1991-02-05 Tetrahydrophthalimides, and their production and use as herbicides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP56180046A JPS5879961A (en) 1981-11-09 1981-11-09 O-fluoroaniline derivative and its preparation

Publications (2)

Publication Number Publication Date
JPS5879961A true JPS5879961A (en) 1983-05-13
JPH0251894B2 JPH0251894B2 (en) 1990-11-08

Family

ID=16076534

Family Applications (1)

Application Number Title Priority Date Filing Date
JP56180046A Granted JPS5879961A (en) 1981-03-30 1981-11-09 O-fluoroaniline derivative and its preparation

Country Status (1)

Country Link
JP (1) JPS5879961A (en)

Also Published As

Publication number Publication date
JPH0251894B2 (en) 1990-11-08

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