JPS60222445A - フタル酸化合物 - Google Patents

フタル酸化合物

Info

Publication number
JPS60222445A
JPS60222445A JP59078907A JP7890784A JPS60222445A JP S60222445 A JPS60222445 A JP S60222445A JP 59078907 A JP59078907 A JP 59078907A JP 7890784 A JP7890784 A JP 7890784A JP S60222445 A JPS60222445 A JP S60222445A
Authority
JP
Japan
Prior art keywords
compound
toluene
formula
white crystals
hydroxybenzoate
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.)
Pending
Application number
JP59078907A
Other languages
English (en)
Inventor
Masato Maue
真上　真諭
Sumi Saeki
佐伯　寿美
Takanori Miura
孝則 三浦
Takeshi Inoue
健 井上
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.)
Tanabe Pharma Corp
Original Assignee
Yoshitomi Pharmaceutical Industries 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 Yoshitomi Pharmaceutical Industries Ltd filed Critical Yoshitomi Pharmaceutical Industries Ltd
Priority to JP59078907A priority Critical patent/JPS60222445A/ja
Priority to EP85902124A priority patent/EP0181404B1/en
Priority to US06/748,450 priority patent/US4695649A/en
Priority to PCT/JP1985/000208 priority patent/WO1985004869A1/ja
Priority to DE8585902124T priority patent/DE3575917D1/de
Publication of JPS60222445A publication Critical patent/JPS60222445A/ja
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

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、一般式 〔式中、Ｒは炭素数１〜８個のアルキル基（メチル、エ
チル、プロピル、イソプロピル、ブチル、イソブチル、
第２級ブチル、第３級ブチル、ペンチル、ネオペンチル
、ヘキシル、ヘプチル、オクチル、第３級オクチルなど
）またはベンジル基を示す。〕 で表わされる新規なフタル酸化合物に関する。
一般式（Ｉ）の化合物は、一般式 （式中、Ｘは塩素、臭素などのハロゲン原子を示す。） で表わされる化合物と一般式 （式中、Ｒは前記と同義である。） で表わされる化合物とを適当な溶媒（トルエン、ベンゼ
ン、キシレンなど）中、アミン類（トリエチルアミン、
ピリジン、ジメチルアニリンなど）の存在下に反応させ
ることにより容易に製造することができる。
目的物は、カラムクロマトや再結晶などの常法により精
製される。
本発明化合物は、衛生害虫、たとえばゴキブリや白蟻な
どに対して忌避作用を有し、従って、たとえば害虫忌避
剤として有用である。また、熱可塑性ポリマーに対して
可塑化効率がすぐれているため柔軟性、弾性、可塑性を
増加させ、揮発性も少ないことからポリマーの可塑剤と
しても有効である。
以下、実施例により本発明の詳細な説明する。
実施例１ 冷却管、温度計を付した５００ｍｅ四頚フラスフにｐ−
ヒドロキシ安息香酸ベンジル５６ｇ１　）リエチルアミ
ン２５ｇおよびトルエン６０ｍｅを仕込む。攪拌下、０
〜５℃に保持しながらテレフタル酸ジクロライド２５ｇ
をトルエン１００＋ｎｅに懸濁した液を３時間で滴下す
る。滴下終了後さらに０〜５℃で１時間反応させる。次
いで反応物を濾過し白色の結晶を得る。本品を水１５０
０ｒｎｌで２回、メタノール１０’　００　ｎｒｌで２
回洗浄した後、クロロホルムから再結晶すると、融点１
８６〜１８７℃のテレフタル酸ジ（ｐ−ベンジルオキシ
カルボニルフェニル）の白色結晶が得られる。
実施例２ 冷却管、温度計を付した５００ｍ１！四頚フラスコにｐ
−ヒドロキシ安息香酸ベンジル５６ｇ５Ｆリエチルアミ
ン２５ｇおよびトルエン１６０−を仕込む。攪拌下、０
〜３℃に保持しながらイソフタル酸ジクロライド２５ｇ
をトルエン１００ｍｅに懸濁させた液を３時間で滴下す
る。滴下終了後さらに０〜３℃で１時間反応させる。次
いで反応物を濾過し白色の結晶を得る。本品を水１５０
０ｍｌ’で２回、メタノール１０００−で１回洗浄した
後、ヘキサン−クロロホルム（１：ｌ）混合溶媒から再
結晶すると、融点１０５〜１０７℃のイソフタル酸ジ（
ｐ−ベンジルオキシカルボニルフェニル）の白色結晶が
得られる。
実施例３ 冷却管、温度計を付した５００ｍ１四頚フラスコにｐ−
ヒドロキシ安息香酸ベンジル５６ｇ１　）リエチルアミ
ン２５ｇおよびトルエン１６０ｆｎＩ！ヲ仕込む。攪拌
下θ〜３℃に保持しながらフタル酸ジクロライド２５ｇ
をトルエン１００Ｔｎ！！に溶解させた液を３時間で滴
下する。滴下終了後さらに０〜３℃で１時間反応させる
。次いで反応物を濾過し炉液を水５００ｆｎｌで２回洗
浄後、減圧濃縮しトルエンを留去した後、ヘキサン１０
０ｍｇを加え攪拌すると白色結晶を得る。本品をヘキサ
ン−酢酸エチル（１：ｌ）混合溶媒から再結晶すると、
融点１００〜１０３℃のフタル酸ジ（ｐ−ベンジルオキ
シカルボニルフェニル）の白色結晶が得られる。
実施例４ 冷却管、温度計を付した５００ｍ１四頚フラスコにｐ−
ヒドロキシ安息香酸メチル２０ｇ、）リエチルアミン１
３．１　ｇおよびトルエン１００−を仕込む。攪拌下、
０〜５℃に保持しながらフタル酸ジクロライド１３．２
　ｇをトルエン４０ｙａｆ’に溶解した液を１時間で滴
下する。滴下終了後、さらに〇−５℃で１時間反応させ
る。次いで反応物を水１０００−で３回洗浄した後、減
圧濃縮しトルエンを留去し、残金をトルエンから再結晶
すると、融点１２３〜１２５℃のフタノシ酸ジ（ｐ−メ
トキシカルボニルフェニル）の白色結晶が得られる。
実施例５ 冷却管、温度計を付した１０１００Ｏ！四頚フラスコに
ｐ−ヒドロキシ安息香酸メチル２０ｇ、トリエチルアミ
ン１３．１　ｇおよびトルエン１０Ｍを仕込む。攪拌下
、０〜５℃に保持しながらイソフタル酸ジクロライド１
３．２ｇをトルエンｌｉｏｍｌに懸濁させた液を１時間
で滴下する。滴下終了後メタノ−／Ｌ’５００ｄを加え
、さらに３０分間攪拌する。次いで反応物を濾過し白色
の結晶を得る。
本品を水１０１００Ｏ’で２回、メタノール５００ｍｅ
で１回洗浄した後、酢酸エチル−クロロホルム（１：ｌ
）混合溶媒から再結晶すると、融点２１５〜２１７℃の
イソフタル酸ジ（ｐ−メトキシカル実施例６ イソフタ７Ｌ’！”’ロライドの代りにテレフタル酸タ
ロライドを用いて、実施例５と同様に反応しクロロホル
ムから再結晶すると、融点２４３〜２４５℃のテレフタ
ル酸ジ（ｐ−メトキシカルボニルフェニル）の白色結晶
が得られる。
実施例７ ｐ−ヒドロキシ安息香酸エチルおよびイソフタψ ル酸クロライドを用いて実施例５と同様に反応し、酢酸
エチル−クロロホルム（Ｍｌ）から再結晶すると、融点
１２３〜１２５℃のイソフタル酸ジ（ｐ−エトキシカル
ボニルフェニル）の白色結晶が得られる。
実施例８ ｐ−ヒドロキシ安息香酸エチルとテレフタル酸り）ロラ
イドを用いて実施例５と同様に反応し、酢酸エチル−ク
ロロホルム（Ｍｌ）から再結晶すると、融点１８７〜１
８９℃のテレフタル酸ジ（ｐ−エトキシカルボニルフェ
ニル）の白色結晶カ得られる。
実施例９ ｐ−ヒドロキシ安息香酸プロピルとフタル計なロライド
を用いて実施例４と同様に反応、処理し残金にヘキサン
を加えて結晶化させた後、酢酸エチル−クロロホルム（
Ｍｌ）で再結晶すると、融点８７〜８９℃のフタル酸ジ
（ｐ−プロポキシカルボニルフェニル）の白色結晶が得
られる。
実施例１０ ｐ−ヒドロキシ安息香酸プロピルとテレフタル酸タロラ
イドを用いて実施例５と同様に反応し、ヘキサン−クロ
ロホルム（Ｍｌ）から再結晶すると融点１３６〜１３９
℃のテレフタル酸ジ（ｐ−プロポキシカルボニルフェニ
ル）の白色結晶が得られる。
実施例１１ ｐ−ヒドロキシ安息香酸ブチルとテレフタル酸９３０ラ
イドを用いて実施例５と同様に反応し、ヘキサン−クロ
ロホルム（１：１）から再結晶すると、融点１２８〜１
３１℃のテレフタル酸ジ（ｐ−プトキシカルボニルフェ
ニ／Ｌ／）の白色結晶が得られる。
実施例１２ ｐ−ヒドロキシ安息香酸オクチルとテレフタル訴ロライ
ドを用いて実施例４と同様に反応、処理し残金を酢酸エ
チル−クロロホルム（１：１）で再結晶すると、融点１
０８〜１１０℃のテレフタル酸ジ（ｐ−オクチルオキシ
カルボニルフェニル）の白色結晶が得られる。
実施例１３ ｐ−ヒドロキシ安息香酸オクチルとイソフタル碇？ロラ
イドを用いて実施例４．と同様に反応、処理すると、淡
黄色油状のイソフタル酸ジ（ｐ−オクチルオキシカルポ
ニルフエニｙ）が得られる。
代理人　弁理士　高宮城　勝 手続（甫正書（自発） 昭和６０年４月ｌＯ日 特許庁長官　志　賀　学　殿 昭和５９年特許願第７８９０７号 ２、発明の名称 フタル酸化合物 ３、補正をする者 事件との関係　特許出願人 住　所　大阪市東区平野町３丁目３５番地名称　吉富製
薬株式会社 （６７２）　代表者　奥　１）　充　夫４、代理人 住　所　大阪市東区平野町３丁目３５番地６、補正の内
容 明細書第２頁９行（式を１行と数える。）の一般式（Ｉ
ｆ）の構造式を ［ 」 に訂正する。
以　上

Claims (1)

  1. 【特許請求の範囲】 一般式 （式中、Ｒは炭素数１〜８個のアルキル基またはベンジ
    ル基を示す。） で表わされるフタル酸化合物。
JP59078907A 1984-04-19 1984-04-19 フタル酸化合物 Pending JPS60222445A (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP59078907A JPS60222445A (ja) 1984-04-19 1984-04-19 フタル酸化合物
EP85902124A EP0181404B1 (en) 1984-04-19 1985-04-16 Phthalate compounds
US06/748,450 US4695649A (en) 1984-04-19 1985-04-16 Phthalate compounds
PCT/JP1985/000208 WO1985004869A1 (fr) 1984-04-19 1985-04-16 Composes de phthalate
DE8585902124T DE3575917D1 (de) 1984-04-19 1985-04-16 Phthalatverbindungen.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP59078907A JPS60222445A (ja) 1984-04-19 1984-04-19 フタル酸化合物

Publications (1)

Publication Number Publication Date
JPS60222445A true JPS60222445A (ja) 1985-11-07

Family

ID=13674899

Family Applications (1)

Application Number Title Priority Date Filing Date
JP59078907A Pending JPS60222445A (ja) 1984-04-19 1984-04-19 フタル酸化合物

Country Status (5)

Country Link
US (1) US4695649A (ja)
EP (1) EP0181404B1 (ja)
JP (1) JPS60222445A (ja)
DE (1) DE3575917D1 (ja)
WO (1) WO1985004869A1 (ja)

Cited By (1)

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US4695649A (en) 1987-09-22
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EP0181404A4 (en) 1986-07-17
DE3575917D1 (de) 1990-03-15
WO1985004869A1 (fr) 1985-11-07

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