JPH0482857A - New monoterpene and derivative thereof - Google Patents

New monoterpene and derivative thereof

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Publication number
JPH0482857A
JPH0482857A JP19369290A JP19369290A JPH0482857A JP H0482857 A JPH0482857 A JP H0482857A JP 19369290 A JP19369290 A JP 19369290A JP 19369290 A JP19369290 A JP 19369290A JP H0482857 A JPH0482857 A JP H0482857A
Authority
JP
Japan
Prior art keywords
hexane
new
derivative
monoterpene
objective
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
JP19369290A
Other languages
Japanese (ja)
Inventor
Yasumasa Kuwabara
保正 桑原
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.)
Daikin Industries Ltd
Original Assignee
Daikin 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 Daikin Industries Ltd filed Critical Daikin Industries Ltd
Priority to JP19369290A priority Critical patent/JPH0482857A/en
Publication of JPH0482857A publication Critical patent/JPH0482857A/en
Pending legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

NEW MATERIAL:3-Oxo-4-isopropylidene-1-cyclohexene-1-carboxyaldehyde of the formula and its derivatives. USE:Giving citrus aroma, and having antifungal activity against plant pathogenic fungi, thus being useful as a fungicide for plants. PREPARATION:The objective compound can be obtained through isolation from mite. In this case, Rhizoglyphus robini is bred and collected and then immersed in n-hexane for 3 min. The resulting hexane extract is then put to silicate column chromatography followed by elution with n-hexane/ether, thus eluting the objective NEW compound in (90 : 10) and (80 : 20) fractions.

Description

【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、新規モノテルペンに関する。[Detailed description of the invention] [Industrial application field] The present invention relates to novel monoterpenes.

本発明の新規モノテルペンである３−オキソ４−インプ
ロピリデン−１−シクロヘキセン−１カルボキシアルデ
ヒド（以下、ロビナール（ｒ。3-oxo-4-inpropylidene-1-cyclohexene-1carboxaldehyde (hereinafter referred to as Robinal (r)), which is a novel monoterpene of the present invention.

ｂｉｎａｌ）という。）は、食品及び農業害虫であるリ
ゾグリフアメ１０ビニ（Ｒｈｉｚｏｇｌｙｐｈｕｓ　ｒ
ｏｂｉｎｉ）（ロボンネグニ）から単離・構造決定され
た新規モノテルペンである。本発明の化合物はモノチル
で示される化合物であり、以下の物性値を有する。It is called (binal). ) is a food and agricultural pest, Rhizoglyphus r.
This is a new monoterpene isolated and structure determined from Lobonnegni). The compound of the present invention is a compound represented by monotyl, and has the following physical property values.

ＭＳ（′／Ｚ）・１６４．０８４０（Ｍつ。MS('/Z)・164.0840(M.

１４９．１３５ ＧＣ−ＦＴＩＲ：２８］、６．２７１６、６７８ｃｍ Ｕ■（ヘキサン）・λｍａｘ＝　２４５　ｎｍ（ε−３
５０００） ００ｎｍ （ε−４６６０） Ｎ　Ｍ　Ｒ（５００Ｍ　Ｈｚ、　ＣＤ　ＣＱ３）δ−９
，７７（ＩＨ，ｓ）、６．５７　　（ＩＨ，ｔ。149.135 GC-FTIR: 28], 6.2716, 678 cm U■ (hexane)・λmax= 245 nm (ε-3
5000) 00nm (ε-4660) NMR (500MHz, CD CQ3) δ-9
, 77 (IH, s), 6.57 (IH, t.

Ｊ　　−１，４Ｈｚ）、　　２．７３（２Ｈ，Ｌ、　　
　Ｊ＝６゜３４、Ｈｚ）、２．４８（２Ｈ，ｄｔ、Ｊ＝
６．３’４及び１．４Ｈｚ）、２．１６（３Ｈ，ｓ）、
１．９４（３Ｈ，ｓ） Ｃ”ＮＭＲ：δ−１９４，３８（アルデヒド）、１９１
．４．２（ケトン） 本発明のモノテルペンは、ダニ類からの単離により得る
ことができる。すなわぢ、飼育して集めたりゾグリファ
ス・ロビニ（ロビン不タニ）ヲｎへ牛サンに３分間浸漬
した。得られたヘキサン抽出物をケイ酸カラムクロマト
グラフィに供し、ｎ−ヘキサン・エーテルにより溶離す
ると、９０１０及び８０　：２０画分にロビナールが溶
出される。J -1,4Hz), 2.73(2H,L,
J = 6°34, Hz), 2.48 (2H, dt, J =
6.3'4 and 1.4Hz), 2.16 (3H,s),
1.94 (3H, s) C” NMR: δ-194,38 (aldehyde), 191
．． 4.2 (Ketone) The monoterpene of the present invention can be obtained by isolation from mites. In other words, they were bred and collected, and Zoglyphus robinii (Robin futani) was soaked in beef dill for 3 minutes. When the obtained hexane extract is subjected to silicic acid column chromatography and eluted with n-hexane ether, Robinal is eluted in the 9010 and 80:20 fractions.

次に実施例を示し、本発明を説明する。Next, examples will be shown to explain the present invention.

［実施例］ 実施例１ 抗菌試験（ペーパーディスク法） 抗生物質検定用の直径８Ｒｍのペーパーディスクを用い
、抗菌活性は阻止円の直径（ｉｚ）で評価した。[Examples] Example 1 Antibacterial test (paper disk method) Using a paper disk with a diameter of 8 Rm for antibiotic assay, antibacterial activity was evaluated by the diameter of the inhibition circle (iz).

なお、培地としてポテトデキストロースアガーを用い、
ロビナールは下記濃度のヘキサン溶液として用いた。In addition, potato dextrose agar was used as the medium,
Robinal was used as a hexane solution with the following concentration.

阻止円の直径を第１表に示す。The diameters of the blocking circles are shown in Table 1.

注：ＡＡ：アルタナリア・アルタナリア（Ａ、　ａｌｔ
ｅｒｎａｔａ） ＡＮ：アスペルキルス・二カー （Ａ、　ｎｉｇｅｒ） ＦＯ：フザリウム・オキシスポルム （Ｆ　、　ｏｘｙｓｐｏｒｕｍ） Ｐ■：ペニシリウム・バーミキュラータム（Ｐ、　ｖｅ
ｒｍｉｃｕｌａｔｕｍ）Note: AA: Alternaria Alternaria (A, alt
ernata) AN: Aspercillus nikah (A, niger) FO: Fusarium oxysporum (F, oxysporum) P■: Penicillium vermicularatum (P, ve
rmiculatum)

Claims (1)

【特許請求の範囲】 １、式： ▲数式、化学式、表等があります▼ で示される新規モノテルペン及びその誘導体。[Claims] 1. Formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ A novel monoterpene and its derivatives represented by
JP19369290A 1990-07-20 1990-07-20 New monoterpene and derivative thereof Pending JPH0482857A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP19369290A JPH0482857A (en) 1990-07-20 1990-07-20 New monoterpene and derivative thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP19369290A JPH0482857A (en) 1990-07-20 1990-07-20 New monoterpene and derivative thereof

Publications (1)

Publication Number Publication Date
JPH0482857A true JPH0482857A (en) 1992-03-16

Family

ID=16312195

Family Applications (1)

Application Number Title Priority Date Filing Date
JP19369290A Pending JPH0482857A (en) 1990-07-20 1990-07-20 New monoterpene and derivative thereof

Country Status (1)

Country Link
JP (1) JPH0482857A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6102111A (en) * 1996-10-17 2000-08-15 Honda Giken Kogyo Kabushiki Kaisha Heat exchanger

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6102111A (en) * 1996-10-17 2000-08-15 Honda Giken Kogyo Kabushiki Kaisha Heat exchanger

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