JPH0228589B2 - - Google Patents

Info

Publication number
JPH0228589B2
JPH0228589B2 JP54009269A JP926979A JPH0228589B2 JP H0228589 B2 JPH0228589 B2 JP H0228589B2 JP 54009269 A JP54009269 A JP 54009269A JP 926979 A JP926979 A JP 926979A JP H0228589 B2 JPH0228589 B2 JP H0228589B2
Authority
JP
Japan
Prior art keywords
formula
dimethylphenyl
compound according
compound
general formula
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 - Lifetime
Application number
JP54009269A
Other languages
English (en)
Other versions
JPS54135727A (en
Inventor
Bosoone Enriko
Kamatsuji Jiobanni
De Furiisu Ramuberutosu
Garabaria Karuro
Garurasukeruri Ruiji
Gotsutsuo Furanko
Korunerisu Oobereemu Yan
Rorutsuso Shimoone
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.)
Montedison SpA
Original Assignee
Montedison SpA
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
Priority claimed from IT1989678A external-priority patent/IT1111159B/it
Priority claimed from IT2529578A external-priority patent/IT1101052B/it
Application filed by Montedison SpA filed Critical Montedison SpA
Publication of JPS54135727A publication Critical patent/JPS54135727A/ja
Publication of JPH0228589B2 publication Critical patent/JPH0228589B2/ja
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)

Description

【発明の詳細な説明】
本発明は新規なアシルアニリンに係わり、更に
特定するなら、殺菌作用を有する新規なアシルア
ニリン、その製造および用途に係わる。 近年、種々置換せるフエニルおよび各種のアシ
ル基を窒素原子上に有するいくつかのグリシン並
びにアニリン誘導体の殺バクテリア作用および殺
菌作用が報告されている。特に、アシル基は、α
―又はβ―ハロアカノイルからなり（チバ・ガイ
ギーのドイツ国特許出願DOS第2513789号）、或
は、種々の基に結合せる酸素又は硫黄の原子によ
つてα―位が置換されたアセチル基よりなり（チ
バ・ガイギーのフランス国特許出願第7510722
号）、或はまた、２―フロイル基、２―チエノイ
ル基又はピリジル２―カルボキシル基よりなる
（チバ・ガイギーのドイツ国特許出願DOS第
2513732号および同第2513788号）。窒素原子上に
２，６―ジアルキルフエニルと、シクロプロパノ
イル、アクリロイルおよびクロトノイルのうち１
種を有するメチルアラニン酸塩の殺微生物活性を
亦報告されている（スイス国特許出願4998／74お
よび同2906／75）。 而して、殺菌作用を有するアシルアニリンの新
規な誘導体に関して研究することの意義は、該誘
導体にその高い殺菌作用と植物毒の不在とを見出
す必要性から生ずる。事実、既に知られたいくつ
かの化合物はすぐれた殺菌作用を示すが、それは
また、菌による伝染病から保護すべき植物に対し
ても毒性を示す。 然るに、本発明者は、下記一般式： に相当する新規な殺菌性アシルアニリンを発見し
た。 式中、
【式】（Ｒ＝C1〜C3アルキル） Ｚ＝フエニル、メチル置換フエニル、ベンジ
ル、チエニルメチル。 式の化合物は高い殺菌作用と低い植物毒性を
有する。 一般式（）に相当するアシルアニリンの合成
は概ね、一般式： ［式中Ｘは既述の意味を有する］のアニリンと式 ［式中Ｚは既述の意味を有する］の化合物とをハ
ロゲン酸受容体塩基又はジメチルホルムアミドの
存在で縮合反応させることによつて遂行される。 一般式を有するアニリンのいくつかは市販さ
れており、他は、既知反応により、２，６―ジ置
換アニリンを出発物質として容易に取得される。
一般式の化合物の例として、塩化ベンゾイル、
フエニルアセチルクロリド等を挙げることができ
る。 上記の方法に従つて表に掲載の化合物を調製
した。
【表】
【表】 ｔ＝三重項
ｑ＝四重項
ｍ＝多重項
一般式の化合物は植物病因性菌に対しすぐれ
た殺菌活性を有し、而してそれにより示される作
用は予防的（なぜなら、それが病気の発生を未然
に防ぐので）、且つ治療的（すなわち既に伝染病
が進行しているときも効果的）である。 しかも、本化合物は良好な体系的特性を有する
（すなわち植物の各部分に輸送される）ので、そ
れを葉又は土壌を介して適用することができる。 本発明のいくつかの新規なアシルアニリンの殺
菌作用と植物毒性を表２に示す。これらの資料
を、ドイツ国特許出願第2513788号に記載の既知
化合物「フラルアキシル（Furalaxyl）」および
同第2515091号に記載の「リドミル（Ridomil）」
に関する資料と比較する。殺菌作用と植物毒性に
関する値は例３おび例４に記載の如く測定した。
而して、これらの比較から明らかな如く、殺菌作
用については本発明の化合物と「フラルアキシ
ル」および「リドミル」とは同等であるが、植物
毒性については本発明化合物の方がはるかに低
い。
【表】
【表】 殺菌性化合物を、その殺菌作用と植物毒性との
間に最良均衡をもたらす用量で用いることによ
り、植物毒性によつて惹起される植物の損傷を避
けることはできない。 事実、殺菌剤を実際に農園芸に用いるとき、作
業者が行う処置の正確さおよび頻度或は気象条件
（特に降水頻度）に関連して、植物上に事実上残
留する殺菌剤量は著しく変動することがある。そ
れ故、十分な活性と広い安全範囲を有し而して多
量用いても植物を損わないような入手容易な殺菌
剤を得ることが必要である。 種々の適用量での本発明化合物と「フラルアキ
シル」および「リドミル」との殺菌作用および植
物毒性を下記表３に示す。 表３に記載の資料を比較して明らかなように、
殺菌作用については本発明の化合物と対照化合物
とは同程度であるが、植物毒性については、適用
量の増加につれ本発明化合物の方がかなり低い。
【表】 本発明を更に例示するために下記例を示す。 例 １ Ｎ―（２，６―ジメチルフエニル）―Ｎ―（１
―カルボメトキシエチル）フエニルアセトアミ
ド（表１中化合物４）の製造 ジメチルホルムアミド（１ml）とトルエン
（150ml）に溶かしたＮ―（１―カルボメトキシエ
チル）―２，６―ジメチルアニリン（純度95％）
（21.2ｇ、0.1モル）の溶液にフエニルアセチルク
ロリド17ｇ（0.11モル）を30分間にわたり室温で
滴加した。この反応混合物を室温で１時間、還流
温度で３時間かき混ぜ、しかるのち室温を冷却
し、５％のNaHCO3水溶液次いで水で洗浄した。
有機相を分離し、無水のNa2SO4で脱水した。 溶剤を蒸発させ、得られた粗生成物をリグロイ
ン（75〜120℃）から再晶出させることによつて、
初期生成物（白色固体、mp78〜80℃）26ｇを得
た。 例 ２ 表１の化合物１〜３および５を対応する中間体
から例１に記載の如く取得した。 例 ３ ぶどうべと病菌〔プラスモパラ・ビチコラ
（B.et C.）・ベルル・エト・デ・トニ〕に対す
る治療作用 温度25℃、相対湿度60％に状態調整せる環境で
はち栽培したぶどう品種ドルセトの葉裏に、プラ
スモパラ・ビチコラの分生子の水性懸濁物（１c.c.
当りの分生子200000個）を噴霧した。21℃で飽和
湿度の環境に24時間滞留させたのち、植物を三つ
のグループに分けた。感染から夫々１日、２日そ
して３日後、試験化合物の水性アセトン溶液〔ア
セトン20％（容／容）〕を葉の両面に噴霧するこ
とによつて、各グループの植物と処置した。 インキユベーシヨン（７日）のあと、感染のひ
どさを100（無損傷の植物）〜０（完全に感染され
た植物）範囲の評価等級指数に従つて目視評価し
た。その結果を表２および表３に示す。 例 ４ 植物毒性の測定 25℃、相対湿度60％に状態調整せる室内ではち
栽培したぶどう植物品種ドルセトの葉の両面に試
験化合物の水性アセトン溶液〔アセトン20％
（容／容）〕を噴霧することによつて、該植物を処
置した。 ７日後、植物毒症状のひどさを、100（完全に損
われた植物）〜０（無損傷植物）範囲の評価等級
指数に従つて目で評価した。その結果を表２およ
び３に示す。

Claims (1)

  1. 【特許請求の範囲】 １ 一般式 ［式中、 【式】（Ｒ＝C1〜C3アルキル） Ｚ＝フエニル、メチル置換フエニル、ベンジ
    ル、チエニルメチル］ の化合物。 ２ Ｎ―（２，６―ジメチルフエニル）―Ｎ―
    （１―カルボメトキシエチル）ベンズアミドであ
    る特許請求の範囲第１項記載の化合物。 ３ Ｎ―（２，６―ジメチルフエニル）―Ｎ―
    （１―カルボイソプロポキシエチル）ベンズアミ
    ドである特許請求の範囲第１項記載の化合物。 ４ Ｎ―（２，６―ジメチルフエニル）―Ｎ―
    （１―カルボメトキシエチル）―２―メチルベン
    ズアミドである特許請求の範囲第１項記載の化合
    物。 ５ Ｎ―（２，６―ジメチルフエニル）―Ｎ―
    （１―カルボメトキシエチル）―２―チエニルア
    セトアミドである特許請求の範囲第１項記載の化
    合物。 ６ Ｎ―（２，６―ジメチルフエニル）―Ｎ―
    （１―カルボメトキシエチル）フエニルアセトア
    ミドである特許請求の範囲第１項記載の化合物。 ７ 一般式 ［式中、 【式】（Ｒ＝C1〜C3アルキル） Ｚ＝フエニル、メチル置換フエニル、ベンジ
    ル、チエニルメチル］ の化合物を製造するに当たり、一般式 ［式中Ｘは既述の意味を有する］のアニリンと式 ［式中Ｚは既述の意味を有する］のカルボン酸塩
    化物とを、不活性溶剤中、ハロゲン酸受容体塩基
    又はジメチルホルムアミドの存在で反応させるこ
    とを特徴とする方法。 ８ 活性成分として、一般式 ［式中、 【式】（Ｒ＝C1〜C3アルキル） Ｚ＝フエニル、メチル置換フエニル、ベンジ
    ル、チエニルメチル］ の化合物１種又は２種以上を含有する殺菌用組成
    物。
JP926979A 1978-02-02 1979-01-31 Fungicidal novel acylanilines Granted JPS54135727A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT1989678A IT1111159B (it) 1978-02-02 1978-02-02 Alfa-carbnil derivati di acetanilidi ad azione fungicida
IT2529578A IT1101052B (it) 1978-07-04 1978-07-04 Acilaniline ad azione fungicida

Publications (2)

Publication Number Publication Date
JPS54135727A JPS54135727A (en) 1979-10-22
JPH0228589B2 true JPH0228589B2 (ja) 1990-06-25

Family

ID=26327339

Family Applications (1)

Application Number Title Priority Date Filing Date
JP926979A Granted JPS54135727A (en) 1978-02-02 1979-01-31 Fungicidal novel acylanilines

Country Status (27)

Country Link
US (2) US4291049A (ja)
JP (1) JPS54135727A (ja)
AR (1) AR222648A1 (ja)
AT (1) AT367027B (ja)
AU (1) AU531955B2 (ja)
BG (1) BG28977A3 (ja)
BR (1) BR7900599A (ja)
CA (1) CA1130299A (ja)
CH (1) CH639641A5 (ja)
CS (1) CS203031B2 (ja)
CY (1) CY1173A (ja)
DD (2) DD142042A5 (ja)
DE (1) DE2903612A1 (ja)
EG (1) EG13956A (ja)
ES (1) ES477353A1 (ja)
FR (2) FR2416216B1 (ja)
GB (1) GB2023132B (ja)
GR (1) GR73057B (ja)
HU (1) HU182903B (ja)
KE (1) KE3253A (ja)
LU (1) LU80852A1 (ja)
MX (1) MX5631E (ja)
NZ (1) NZ189497A (ja)
PT (1) PT69153A (ja)
RO (1) RO76487A (ja)
SU (1) SU1128832A3 (ja)
YU (1) YU42297B (ja)

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CH639641A5 (it) 1983-11-30
DD150421A5 (de) 1981-09-02
US4291049A (en) 1981-09-22
SU1128832A3 (ru) 1984-12-07
DE2903612A1 (de) 1979-08-09
FR2454270A1 (fr) 1980-11-14
BR7900599A (pt) 1979-08-28
GR73057B (ja) 1984-01-27
ATA79079A (de) 1981-10-15
CS203031B2 (en) 1981-02-27
CA1130299A (en) 1982-08-24
YU23779A (en) 1983-02-28
DD142042A5 (de) 1980-06-04
CY1173A (en) 1983-06-10
DE2903612C2 (ja) 1988-12-22
AR222648A1 (es) 1981-06-15
AU531955B2 (en) 1983-09-15
PT69153A (en) 1979-02-01
ES477353A1 (es) 1980-01-16
JPS54135727A (en) 1979-10-22
HU182903B (en) 1984-03-28
YU42297B (en) 1988-08-31
RO76487A (ro) 1981-04-30
GB2023132B (en) 1982-08-25
FR2416216B1 (fr) 1985-12-20
KE3253A (en) 1983-03-04
MX5631E (es) 1983-11-15
FR2454270B1 (ja) 1983-11-10
GB2023132A (en) 1979-12-28
LU80852A1 (fr) 1979-09-07
AT367027B (de) 1982-05-25
BG28977A3 (en) 1980-08-15
US4425357A (en) 1984-01-10
AU4375179A (en) 1979-08-09
FR2416216A1 (fr) 1979-08-31
EG13956A (en) 1984-06-30
NZ189497A (en) 1981-03-16

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