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JPS5826860A - スルホンアミド基を含有するフエノキシ安息香酸誘導体の製造方法 - Google Patents

スルホンアミド基を含有するフエノキシ安息香酸誘導体の製造方法

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Publication number
JPS5826860A
JPS5826860A JP57130216A JP13021682A JPS5826860A JP S5826860 A JPS5826860 A JP S5826860A JP 57130216 A JP57130216 A JP 57130216A JP 13021682 A JP13021682 A JP 13021682A JP S5826860 A JPS5826860 A JP S5826860A
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Japan
Prior art keywords
group
formula
reaction
carbon atoms
alkyl
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
JP57130216A
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English (en)
Other versions
JPH0149262B2 (ja
Inventor
エル−アマデイ・アイ・ヘイバ
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.)
Bayer CropScience SA
Original Assignee
Rhone Poulenc Agrochimie SA
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Application filed by Rhone Poulenc Agrochimie SA filed Critical Rhone Poulenc Agrochimie SA
Publication of JPS5826860A publication Critical patent/JPS5826860A/ja
Publication of JPH0149262B2 publication Critical patent/JPH0149262B2/ja
Granted legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N1/00—Preservation of bodies of humans or animals, or parts thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
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    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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    • C07D333/30—Hetero atoms other than halogen
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

Description

【発明の詳細な説明】 本発明は、除草性を有するスルホンアミド基を含んだ載
る朴のフェノキシ安息看酸訪導体の改良製造方法に関；
するものである。
スルホンアミド基を有するフェノキシ安息香酸の除琴性
誘導体は、ヨーロッパ牲許出顧第３，４１６号および２
３，３９２号各明細書から公知である。
これらの特許出願明細書は、式 〔上記式中人は水素、弗素、塩素、臭素、沃素、ニトロ
基、−Ｎ”ＮＣＦｓ＋　ＰＯｓＨｓおよび１〜４個の炭
素原子を有するそのアルキルエステル基、ＭｉＮＨＯＨ
，＜、カルボキシル基もしくは゛その官能性誘導基のｌ
ｓ１モノアルキルアミノもしくはジアルキルアミノ基、
基ＮＨ−ＣＯ−Ｒ”　（ここで　Ｒ１はアルキル、アル
コキシ、モノアルキルアミノｌはアルキルまたはフェニ
ル基である）、ＮＨｃｏＮＨｓへｒ　（ここで、Ｐは上
記の意味を有する）、アルキルチオ、アルキルスルフィ
ニル、アルキルスルホニル、ジアルキルスルホニオ、シ
アノスルホニル、ヒト四キシ、アルカノイルオキシ、ア
ルコキシ、アルコキシカルボニルで置換され九アルコキ
シ、８Ｈ，ニトロソ、−８ＣＮ。
であ如、　　　　　　。
Ｂ灯水素、弗素、塩素、臭素、沃素、アルキル、アル；
キシ、アルキルスルフィニル４Ｌ＜はアルキルスルホニ
ル基、Ｃ１２，Ｎｏ！、　ＣＮ、　ＮＨ，ｌ。
ＮＨＣＯＲ”　（ここでＨ１ｄ上記に定款した通シであ
る）またはｃｏ幽ｆｉｂ。
Ｃは水素、ハロゲンまたはアルキルもしくはジアルキル
アミノ基であり、 Ｄは弗素、塩素、臭素、沃素またはＣＦｓ＋アルキルチ
オ、アルキルスルフィニル、アルキルスルホニル、ハロ
ゲンアルキル、スルファモイル、ホルミル、アルキルカ
ルボニル、ＣＮまたハシメチルアミノ基であυ、 五は水素、ハロゲンアルキル、アルコキシ、アルキルス
ルフィニルまたれアルキルスルホニル基、ＣＮＩ　ＯＦ
、、　１％、　ＣＯ隅またはＮＨベトＲ１（ここでＢ１
１１上記の意味を有する）でｉｂ、ＦはＢについ゛て示
した意味の１つを有し、Ｒは基−ＣＯＮ（Ｒ’）毅５で
あル、ここでｔは水素または１〜４個の炭素原子を有す
るアルキル基であシ、 Ｒａけフェニル、ピリジルまたはチェニル基（これらの
基は任意的に、１個もしくはそれ以上のハロゲン原子、
アルキル基もしくはニトロ基によ多置換されていてもよ
い）、２〜４個の炭素原子を有するアルケニルもしくは
アルキニル基、または１〜４個の炭素原子を有するアル
キル基（任意的に、１個もしくはそれ以上の弗素、塩素
、臭素もしくは沃素原子、好ましくはＣＦ３により置換
されていてもよく、または１個屯しくけそれ以上の次の
置換基により置換されていてもよい：カルボキシル、２
〜５個の炭素原子を有するアルコキシカルボニル、２〜
５個の炭素原子を有するアルキルカルボニル、アルキル
部分が１〜４個の炭素原子を有するモノアルキルカルバ
モイルもしくハシアルキルカルバモイル、それぞれ１〜
４個の炭素原子を有するアルキルチオ、アルキルスルフ
ィニル、アルキルスルホニル、２〜５個の炭素原子を有
するアルキルカルボニルオキシ、２〜５個の炭素原子を
有スるアルキルカルボニルアミノ甘たはシアノ基〕 の化合物とその塩とを開示している。
公知方法においては、式（１）の化合物は、式〔式中、
ｘＨ塩素、臭素もしくは沃素であり、Ａ、Ｂ、Ｃ，Ｄ、
ＥおよびＦは上記の意味を有する〕 の中間体の蒙ノ・ロゲン化物を式 ％式％（２） 〔式中、では上記の意味を有する〕 のスルホンアミドと２５〜１４０℃の温度にて酸受容体
の存在下、特にたとえばＮ、Ｎ−７／メチルアニリンも
しく祉ピリジンのような第３級アきン、たとえに無水炭
酸カリウムのようなアルカリ金属巌酸塩、またはたとえ
ば弗化セシウムのよう表アルカリ金島弗化物の存在下で
反応させることによシ製造することができる。
ｔが水素原子である式（１）の化合物は、公知方法によ
シたとえば１〜４個のＪｉ２素原子を有するジアゾアル
カンとの反応によジアルキル化して、ｔが１〜４個の炭
素原子を有するアルキル基である対応する化合物を生成
させることができる。
式（…）の化合物と式（２）の化合物との縮合に関する
この方法は多くの欠点を有する。たとえば、収率が好ま
しくない（たとえば、ヨーロッパ特許出願第２３．８９
２号の実施例１４については収率が２７チであり、また
実施例３４について社収率９．５％と算定できる）。ジ
アシル化反応の促進によシ収率が低下するのであるか、
その主な原因は酸受容体の存在であると考えられる。さ
らに、酸受容体の使用により最終生成物の単離および精
製がより困難になり、かつその費用も一層高価になるＣ 本発明の一目的は、これらの欠点を克服することである
。
本発明による方法は、酸ハロゲン化物（好ましくは塩化
物、臭化物または沃化物）を、酸受容体の不存在下、か
つハロゲン化水素酸（ＨＣＬ、　ＨＢｒ。
ＨＩ）が生成されるそばから気体として反応媒体よシ除
去されるような温度、シかも式（１）の反応生成物の°
′認めうる分解”を伴なわないような温度にて、式（２
）のスルホ／アミドと反応させることを特徴とする。
本発明の方法によれは、フェノキシ安息香酸のスルホン
アミド誘導体が相当に高い収率で得ることができ、たと
えば、少なくとも約３０％しはしば少なくとも約５０％
という収率で得られ、しかも最終生成物の回収および精
製操作Ｌ１公知方法の場合よりもずっと簡単である。
実際上、本発明に使用する酸ハロゲン化物は式（Ｉｔ）
の酸ハロゲン化物である。Ａが基ＮＯＩまたは弗素、塩
素、臭棄もしくは沃素原子であり、Ｂがハロゲン原子で
あり、Ｃ，ＥおよびＦが水素原子であシかつＤが基ＣＦ
、であるような式のハロゲン化物を使用するのが好適で
ある。さらに、Ｒｓがアルキル基、特にＣＨ３または基
ＣＦＩであるような式（４）のスルホンアミドを使用す
るのも好適である３、本発明の方法を行ないうる温度は
、特に式（ＩＩ）の酸ハロゲン化物または式（至）のス
ルホンアミドのいずれかが大過剰に存在するかどうか、
或いは触媒特性を有する溶剤を使用するかしないかに依
存して、種々変わるであろう。
たとえば、酸ハロゲン化物（ＩＩ）が大過剰に存在する
場合、すなわち（Ｉ）／（２）のモル比が約１．５〜５
の範囲である場合、この酸ハロゲン化物（ＩＩ）は反応
用溶媒として役立たせることができ、反応温度を８０〜
２００℃とすることができるが、好ましくは９０〜１６
０℃の範囲である。
未反応のハロゲン化物（１）は、これを不活性溶剤たと
えば炭化水素、特にペンタン、ヘキサン、ヘプタン、シ
クロペンタン、シクロヘキサン、シクロヘプタン、ベン
ゼン、トルエン４Ｌ＜ｔｉキシレン、ハロゲン化炭化水
素、特にクロルベンゼン、ＣＳ、、テトラヒドロ７ラン
、ジオキサンなどで洗浄するごとによｐ反応媒体から回
収することができるＯ 過剰量のスルホンアミドを使用する場合、すなわち化合
物（４）／（Ｉ）のモル比が１．５〜５の範囲である場
合、反応温度は一般に９０〜２００℃、好ましくは１４
０〜１６０℃である０いずれの場合において・も、反応
温度は、少なくとも反応媒体を溶融させるのに充分なＩ
ｔ度でなけれにならない０過剰のスルホンアミド（２）
は、これを水またはこの反応体（２）に対して不活性な
他の溶剤によル洗浄して反応媒体から回収することがで
きる。
さらに、反応体は反応温度より高い沸点を有する不活性
溶剤、たとえば塩素化もしくは非塩素化液体炭ｆ化水素
、たとえばベンゼン、トルエン、キシレン、キシレンの
混合物またはクメンに溶解させることもでき、この場合
、最高反応温度は溶剤の沸点よりわずか低くするのが有
利である。たとえば、沸点が約１５３℃であるクメンの
場合、反応は好ましくは１３０〜１５０℃で行なわれる
。
不活性溶剤の使用は、工業規模の方法において一層良好
な熱移動を可能にするという実用的利点を有する。さら
に、これは反応媒体の局部的過熱の防止にも役立つ＠ 本発明の他の具体例によれば、酸ハロゲン化物（１）と
スルホンアミド（２）との反応によジフェノキシベンゾ
イルスルホンアミド（１）を生成させるための触媒作用
を有する溶剤が使用される０この点でジメチルホルムア
ミド（−ＤＭＦ、　　これは約１５４℃で沸とうする）
およびジメチルアセトアミド（−ＤＭＡＣ，これは約１
６４℃で沸とうする）が特に有利であル、それらの使用
によシ、反応を比較的低い温度、たとえば８０〜１２０
℃、好ましくは９０〜１１０℃の温度、或いはこれら溶
剤の沸点よシ僅かに低い温度において実施できるように
な）、かつ、反応速度はよシ高速となる。
以下、実施例により本発明を説明しかつどのように実施
されうるかを具体的に示すが、本発−〇範囲はこれによ
シ限定されるものでない。
！上皇ユ メタンスルホンアミ）”（ｚｇ、０．０２１モル）を５
−（２’−クロル−４’−（）リフルオロメチル）−フ
ェノキシフ−２−二トローベンゾイルクロライド（３，
８ｇ、　ｏ、ｏ　１モル）と混合した。この混合物を１
５０℃にて２０分間加熱した。塩酸を、生成されるそば
から反応媒体より放出させた。この媒体を冷却して黒色
油状物を得、これを水酸化ナトリウム水溶液中に溶解し
た。この溶液を濾過しそしてｐ液を希塩酸で酸性化させ
、これによシ式（転）の生成物を沈澱させた。かくして
、収率７１チをもって、１９５〜１９７℃にて溶融しが
っ１．６９２ｃｒｎ″″’（Ｃ−０基）に赤外吸収帯を
有する生成物（３，ｔｇ）が得られた。仁の生成物は式
実施例１を反復したが、この場合２５０ｇの酸塩化物と
１３０ｇのメタンスルホンアミドとヲ使用した。反応生
成物は、混合物を冷却した後にイングロパノールからの
再結晶によシ直接に単離し九〇これによシ、式（転）の
生成物が収率６４％（１８１ｇ）で得られた。この生成
物の構造は、赤外吸収スペクトル（１，６９２ｅｍ−’
における吸収帯）および核磁気共鳴スペクトル（ａ、ｓ
ｐ−にてシングレット、８．０７　ｐｐｍにてマルチプ
レット）Ｋよシ確諺された。
比較のために、ヨーロッパ特許出願第２３．３９２号の
実施例に記載の方法を使用し、ピリジンを酸受容体とし
て使用して反応を行った場合、収率は僅か２５％でちっ
た。
代理人斧珊士今　　村　　　　元

Claims (1)

  1. 【特許請求の範囲】 （１１式 〔式中、人は水素、弗素、塩素、臭素、沃素。 ニトロ基＋　　Ｎ＝ＮＣＦｇ　ｒ　ＰＯｎ　＆および１
    〜４個の炭素原子を有するそのアルキルエステル基、Ｍ
    Ｈｓ　、　ＮＨＯＨ−Ｎ黛、カルボキシル基もしくはそ
    の一官能性誘導基の１種、モノアルキルアミノもしくは
    ジアルキルアミン基、基ＮＨ−ＣＯ−Ｒ’（ここで、Ｗ
    はアルキル、アルコキシ、モノアルキルこで、Ｒ３はア
    ルキルまたはフェニル基である）、ＮＨＣＯＮＨ８０，
    Ｒ”　（ここで、Ｗは上記の意味を有すル）、アルキル
    チオ、アルキルスルフィニル、アルキルスルホニル、ジ
    アルキルスルホニオ、シアノスルホニル、ヒドロキシル
    、アルカノイルオキシ、アルコキシ、アルコキシカルボ
    ニルで置換されたアルコキシ、ＳＨ，ニトロソ、−８Ｃ
    Ｎ。 あり、　　　　　　　　。 Ｂは水素、弗素、塩素、臭素、沃素、アルキル、アルコ
    キシ、アルキルスルフィニル４Ｌ＜はアルキルスルホニ
    ル基、ｃＦ’ｓ、　ＮＯｘ＋　ＣＮ＋　ＮＨ２゜ＮＨＣ
    ＯＲ’　　（ここで　Ｒ１は上記に定義した通シである
    ）またはＣ０ＮＨＩであシ、 Ｃは水素、ハロゲンまたはアルキルもしくはジアルキル
    アミノ基であり、 Ｄは弗素、塩素、臭素、沃素またはｃＦｓ、アルキルチ
    オ、アルキルスルフィニル、アルキルスルホニル、ハロ
    ゲノアルキル、スルファモイル、ホルミル、アルキルカ
    ルボニル、ＣＮま九はジメチル７電ノ基であシ、 Σは水素、ハロゲノアルキル、アルコキシ、アルキルス
    ルフィニルまたはアルキルスルホニル基、ＣＮ、　ＣＦ
    ｓ、　Ｎｕｓ、　Ｃ０ＮＨｚまたｉｆ　ＮＨ−Ｃｏ−Ｒ
    ”（ここで、Ｒ囃上記の意味を有する）であり、ＦはＢ
    について示した意味の１つを有し、Ｒは基−ＣＯＮ（Ｒ
    ’）　８０ｔＲ”であシ、ここでＲ４は水素、または１
    〜４個の炭素原子を有するアルキル基であシ、 Ｗはフェニル、ピリジルまたはチェニル基（これらの基
    は任意的に、１個もしくはそれ以上のハロゲン原子、ア
    ルキル基本しくはニトロ基によ）置換されていてもよい
    ）、２〜４個の炭素原子を有するアルケニルもしくはア
    ルキニル基、または１〜４個の炭素原子を有するアルキ
    ル基（任意的に、１個もしくはそれ以上の弗素、塩素、
    臭素もしくは沃素原子、好ましくはＣＦ３により置換さ
    れていてもよく、または、１個もしくはそれ以上の次の
    置換基により置換されていて本よい二カルボキシル、２
    〜５個の炭素原子を有するアルコキシカルボニル、２〜
    ５個の炭素原子を有するアルキルカルボニル、アルキル
    部分が１〜４個の炭素原子を有するモノアルキルカルバ
    モイル４Ｌ＜ｕジアルキルカルバモイル、それぞれ１〜
    ４個の炭素振４を有するアルキールチオ、アルキルスル
    フィニル、アルキルスルホニル、２〜Ｉｓ個の炭素原子
    を有するアルキルカルボニルオキシ、２〜５個の炭素原
    子を有するアルキルカルボニルアミノまたはシアノ基〕 のスルホンアミド基を有するフェノキシ安息香酸誘導体
    またはその塩を製造する方法において、〔式中、Ｘは塩
    素、臭素もしくは沃素原子であシ、ム、Ｂ、Ｃ，Ｄ、Ｅ
    およびＦ杜式（１）において上記した意味を有する〕 の酸ハロゲン化物を式 ％式％ 〔式中、Ｒ−も上記の意味を有する〕 のスルホンアミドと反応させ、この反応を酸受容体の不
    存在下かつ気体状水素−酸副生物が生成されるそばから
    反応媒体よシ除去されるような温度にて行ない、ただし
    この温度は式（１）の生成切の分解温度よシ低いことを
    特徴とするスルホンアミド基を有するフェノキシ安息香
    酸誘導体またはその塩の製造方法。 （２）反応を過剰量の式（Ｉｔ）の酸ハロゲン原子の存
    在下で行なう特許請求の範囲第１項記載の方法。 （ａ）　　式（１）の酸ハロゲン化物／式＠）のスルホ
    ンアミドのモル比を１．５〜５の範囲内とする特許請求
    の範囲第２項記載の方法。 （４）反応温匿を８０〜２００℃、好ましくは９０〜１
    ６０℃とする特許請求の範囲第２項またはｆｇａ項記載
    の方法。 （５）　　反応を過剰量のスルホンアンドの存在下で行
    なう特許請求の範囲第１項記載の方法。 （６）式（転）のスルホンアミド／式（幻の酸ハロゲン
    化物のモル比を１，５〜５の範囲内とする特許請求の範
    囲第５項記載の方法。 （７）反応温度を９０〜２００℃、好ましくは１４０〜
    １６０℃とする特許請求の範囲第５３Ａｙ九扛第６項記
    載の方法。 （８）反応を、反応温度よ）高い沸点を有する溶剤の存
    在下で行なう特許請求の範Ｈ第１項乃至第７項のいずれ
    かに記載の方法。 （９）溶剤を炭化水素とする特許請求の範囲第８項記載
    の方法。 （転）溶剤をクメンとしかつ温度を１３０〜１５０℃と
    する特許請求の範囲第９項記載の方法。 （ロ）反応を、この反応に関して触媒特性を有する溶剤
    の存在下で行なう特許請求の範囲第１項乃至第８項のい
    ずれかに記載の方法。 （２）溶剤をジメチルホルムアミドもしくはジメチルア
    セドブミドとしかつ温度を８０℃乃至溶剤の沸点の範囲
    内とする特許請求の範囲第１１項記載の方法。 （至）温度を９０℃よシ高くする特許請求の範囲第１１
    項記載の方法。 ０４　　式（１）および（ｎ）にふ・いて、ＢおよびＸ
    が塩素原子であり、Ａが塩素原子まだはＮｏ鵞であり、
    Ｃ１ＥおよびＦが水素原子であシかつＤがＣＦ３である
    特許請求の範囲第１項乃至第１３項のいずれかに記載の
    方法。 （２）Ｒ１がアルキルまたはＣＦ、基、好ましくはメチ
    ル基であるスルホンアミドを使用する特許請求の範囲第
    ６項または第７項記載の方法。 （Ｌｉ２式 の化合物を式 Ｃ＆−ｓｏ、−隅 の化合物と反応させる特許請求の範囲側１項乃至第１５
    項のいずれかに記載の方法◇
JP57130216A 1981-07-27 1982-07-26 スルホンアミド基を含有するフエノキシ安息香酸誘導体の製造方法 Granted JPS5826860A (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US28693881A 1981-07-27 1981-07-27
US286938 1981-07-27

Publications (2)

Publication Number Publication Date
JPS5826860A true JPS5826860A (ja) 1983-02-17
JPH0149262B2 JPH0149262B2 (ja) 1989-10-24

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ID=23100791

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JP57130216A Granted JPS5826860A (ja) 1981-07-27 1982-07-26 スルホンアミド基を含有するフエノキシ安息香酸誘導体の製造方法

Country Status (23)

Country Link
JP (1) JPS5826860A (ja)
KR (1) KR880002591B1 (ja)
AT (1) AT385985B (ja)
BE (1) BE893940A (ja)
BR (1) BR8204357A (ja)
CA (1) CA1194472A (ja)
CH (1) CH652384A5 (ja)
DD (1) DD203716A5 (ja)
DE (1) DE3227847A1 (ja)
DK (1) DK333282A (ja)
ES (1) ES514352A0 (ja)
FR (1) FR2510105A1 (ja)
GB (1) GB2103611B (ja)
HU (1) HU191186B (ja)
IE (1) IE53978B1 (ja)
IL (1) IL66197A (ja)
IT (1) IT1198399B (ja)
LU (1) LU84295A1 (ja)
NL (1) NL8202994A (ja)
PL (1) PL136683B1 (ja)
PT (1) PT75322B (ja)
RO (1) RO85388B (ja)
SU (1) SU1215620A3 (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8628109D0 (en) * 1986-11-25 1986-12-31 Ici Plc Chemical process
CN118922556A (zh) 2021-12-20 2024-11-08 伊努梅里斯公司 多个靶的检测和数字定量

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* Cited by examiner, † Cited by third party
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DE2960664D1 (en) * 1978-01-19 1981-11-19 Ici Plc Diphenyl ether compounds useful as herbicides; methods of using them, processes for preparing them, and herbicidal compositions containing them
DE3068101D1 (en) * 1979-07-18 1984-07-12 Ici Plc Diphenyl ether compounds, and herbicidal compositions and processes utilising them

Also Published As

Publication number Publication date
FR2510105A1 (fr) 1983-01-28
KR840000466A (ko) 1984-02-22
CH652384A5 (fr) 1985-11-15
IT1198399B (it) 1988-12-21
ES8306108A1 (es) 1983-05-01
RO85388A (ro) 1984-11-25
ATA290082A (de) 1987-11-15
KR880002591B1 (ko) 1988-12-03
PL136683B1 (en) 1986-03-31
FR2510105B1 (ja) 1984-09-07
IT8222545A1 (it) 1984-01-23
DE3227847A1 (de) 1983-02-10
JPH0149262B2 (ja) 1989-10-24
GB2103611A (en) 1983-02-23
IE53978B1 (en) 1989-05-10
IL66197A (en) 1985-11-29
PT75322A (fr) 1982-08-01
PL237639A1 (en) 1983-05-23
DK333282A (da) 1983-01-28
NL8202994A (nl) 1983-02-16
SU1215620A3 (ru) 1986-02-28
HU191186B (en) 1987-01-28
ES514352A0 (es) 1983-05-01
LU84295A1 (fr) 1984-03-22
BE893940A (fr) 1983-01-26
GB2103611B (en) 1985-04-03
RO85388B (ro) 1984-11-30
DD203716A5 (de) 1983-11-02
PT75322B (fr) 1985-11-29
CA1194472A (en) 1985-10-01
AT385985B (de) 1988-06-10
IT8222545A0 (it) 1982-07-23
BR8204357A (pt) 1983-07-19
IE821786L (en) 1983-01-27
IL66197A0 (en) 1982-11-30

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