DE3604112A1 - Mesembryanthemum plant extracts and crop protection agents and medicaments containing them - Google Patents

Abstract

The invention relates to mesembryanthemum plant extracts, namely I) viscous liquids, obtainable by pressing the green plant parts and filtering the press juice, then concentrating the press juice, precipitating with sulphuric acid, filtering off the precipitate, washing it with water and making the filtrate combined with the wash water alkaline, using an alkali metal hydroxide solution, to give a pH of at least 10.2, and subsequently separating off the liquid from the precipitate and concentrating by evaporation at a temperature not exceeding 100 DEG C/atmospheric pressure and extracting with tetrahydrofuran and evaporating off the solvent from the extract and II) noncrystalline resin-like substances, obtainable by pressing the green plant parts and filtering the press juice, then concentrating the press juice, precipitating with sulphuric acid, filtering off the precipitate, washing it with water and making the filtrate combined with the wash water alkaline, using an alkali metal hydroxide solution, to give a pH of at least 10.2, and subsequently separating off the liquid from the precipitate and concentrating by evaporation at a temperature not exceeding 100 DEG C/atmospheric pressure and extracting with tetrahydrofuran and removing the residue of this extraction and crop protection agents and medicaments containing them. <IMAGE>

Description

The invention relates to new plant extracts from Mesembryanthemaceae and pesticides containing them, especially against soft and rodents, and drugs, especially those with muscle relaxants Effect, contracting effect on inner Organs, tranquilizer and cardiac effects.

The invention is based on the object, new Plant extracts with superior pest control effects and therapeutic effect as well as containing it Pesticides and pharmaceuticals to accomplish.

The above was surprisingly accomplished by the invention reached.

The invention relates to plant extracts of Mesembryantemaceen, namely

• I) viscous liquids
  obtainable by pressing out the green parts of the plants and filtering the press juice, then concentrating the press juice, precipitating with sulfuric acid, filtering off the precipitate, washing it with water and making the filtrate combined with the wash water or wash water alkaline to an pH value of with an alkali metal hydroxide solution at least 10.2 and subsequent separation of the liquid from the precipitate, which largely consists of magnesium hydroxide, and evaporation at a temperature not exceeding 100 ° C / normal pressure until the syrupy consistency and extraction with tetrahydrofuran and evaporation of the solvent from the extract or
• II) non-crystalline resinous substances,
  obtainable by pressing out the green parts of the plants and filtering the press juice, then concentrating the press juice, precipitating with sulfuric acid, filtering off the precipitate, washing it with water and making the filtrate combined with the wash water or wash water alkaline to an pH value of with an alkaline solution at least 10.2 and subsequent separation of the liquid from the precipitate, which largely consists of magnesium hydroxide, and evaporation at a temperature not exceeding 100 ° C / normal pressure until the syrupy consistency and extraction with tetrahydrofuran and separation of the residue of this extraction.

The concentration of the pressed juice is expedient 1/5 to 1/20, in particular 1/10, of the volume carried out.

The subsequent felling is among others Accompanying the main amount of calcium as calcium sulfate with the aim in which after the separation of the Precipitation contained residual solution the calcium sulfate content as possible to keep low. For this purpose, an 8 to 20% by weight, in particular 10 wt .-%, sulfuric acid used.  

It is advantageous to make alkaline as an alkali lye Sodium hydroxide solution used. The use of a 5 to 20% by weight, in particular 10% by weight, Sodium hydroxide solution preferred. It is also preferred as adjust alkaline pH 10.2 to 11.

Evaporation of the mostly precipitated magnesium hydroxide containing precipitate is separated liquid expedient at a temperature not exceeding 90 ° C / normal pressure, preferably against 90 ° C / normal pressure. Evaporation can also be carried out under a vacuum be, in which case at accordingly lower temperatures can be worked.

Evaporation of the used for extraction Tetrahydrofuranes is useful at 60 ° C / normal pressure temperature not exceeded.

As a residue of the evaporation of the tetrahydrofuran a viscous liquid remains. In contrast, the backlog is Extraction of the syrup with tetrahydrofuran is not crystalline, resinous.

The source plants Mesembryanthemaceae come for example in Mediterranean countries.

The above-ground parts of the Plants, preferably leaves and stems, are used.

According to a preferred embodiment of the invention the plant extracts are those from Mesembryantemum edulis (Carpobrotus edulis)

• a) with a boiling point of 165 to 168 ° C / normal pressure,
• b) with a refractive index of n = 1.4628.
• c) with an IR spectrum according to FIG. 1,
• d) with a thin layer chromatographic R _f value of 0.9 (eluent: n-butanol / methanol / water in a volume ratio of 75: 20: 5, spraying agent: real blue salt B and
• e) with a chemical reaction by cooking with sodium hydroxide solution with the escape of ammonia to a connection that all reactions results in an amino sugar.

These are aromatic smelling light yellow viscous liquids.

According to a further preferred embodiment of the invention, the plant extracts are those of Mesembryanthemum edulis (Carpobrotus edulis)

• a) with an IR spectrum according to FIG. 2 and
• b) thin-layer chromatographic R _f values of R _{f 1} = 0.12 yellow,
  R _{f 2} = 0.18 blue and
  R _{f 3} = 0.34 blue (mobile solvent: n-butanol / methanol / water in a volume ratio of 75: 20: 5; spray reagent: ninhydrin)

This material, which is not crystalline, resinous, consists of 3 compounds, 2 of which result in the reactions of an amino sugar. However, the plant extracts according to the invention can also be those from other mesembryanthemaceae species. examples for this are
Mesembryanthemum eaquilaterum (Carpobrotus aequilaterum),
Mesembryanthemum glaucescens (Carpobrotus glaucescens),
Mesembryanthemum virescens (Carpobrotus virescens),
Mesembryanthemum rossii (Carpobrotus rossii),
Mesembryanthemum modestus (Carpobrotus modestus) and
Mesembryanthemum sarcozona (Carpobrotus sarcozona).

The invention also relates to pesticides, which by a content of 1 or more plant extract (s) according to the invention as active ingredient (s), optionally together with 1 or more usual Pest control compounding agent (s), characterized are. So these pesticides can only 1 or more plant extract (s) according to variant I) of the invention Plant extracts included. But you can too both 1 or more plant extract (s) after the Variant I) of the plant extracts according to the invention and 1 or more plant extract (s) according to variant II) contain the plant extracts according to the invention, wherein the latter the pest control effect of the former strengthened or strengthened synergistically. The pesticides according to the invention have the great advantage that it does not lead to strangers Substances are brought into nature and so there are also no environmental problems with toxic residues.

As already said, serve the invention Pest control primarily for controlling of soft and rodents. As molluscs, against which are the pesticides according to the invention are excellent, are snails and as rodents, against which the pesticides according to the invention Mice have to be emphasized.  

For example, snails are canned 1 mg / 10 g body weight, preferably from 2.5 mg / 10 g Body weight of plant extracts according to variant I) of the plant extracts according to the invention killed. Mice are taken with doses from 15 mg / 10 g body weight Plant extracts according to variant I) of the invention Plant extracts killed while at Doses of 5 to 10 mg / 10 g body weight only one muscle relaxant effect shows. Combinations of Plant extracts according to variant I) and II) of the invention Plant extracts have an even smaller effect Cans fatal to pests.

The invention also relates to pharmaceuticals which contain 1 or more according to the invention Plant extract (s), together if necessary with 1 or more customary pharmaceutical packaging agent (s), Marked are.

The plant extracts according to variant I) of the invention Plant extracts act against pests, especially against soft and rodents, and have one therapeutic effect, especially muscle relaxant Effect, contracting effect on internal organs and tranquilizer effect.

The plant extracts according to variant II) of the invention Plant extracts have a cardiac effect, specifically heart-activating Effect.

The invention is illustrated by the following example explained in more detail.  

example I)

There were 1 kg of the leaves and stems of plants of the Mesembryantemum edulis (Corpobrotus edulis) pressed out and the press juice was filtered (yield 95% of theory).

The mixture was then concentrated to 1/10 of the volume and with 1 ml of 10 wt .-% sulfuric acid the undesirable Accompanying substances, including the Most of the calcium precipitated and then the Precipitate filtered off, resulting in the after separation of the precipitation solution obtained Calcium sulfate content was kept low and afterwards the calcium sulfate precipitate was filtered off. This The precipitate was washed twice with 10 ml of water each time and the filtrate combined with the washings became with a 10 wt .-% sodium hydroxide solution to a pH made alkaline by 10.2.

From the failed magnesium hydroxide Liquid separated and at a temperature against 90 ° C / normal pressure up to a syrupy consistency evaporated.

The syrup was 3 times with 10 ml of tetrahydrofuran extracted and the solvent was at a Temperature evaporated against 60 ° C / normal pressure.

A 1 g (0.1% of theory) remained as residue. an aromatic smelling light yellow viscous liquid.

• a) Boiling point 165 to 168 ° C / normal pressure.  
• b) Refractive index: n = 1.4828.
• c) IR spectrum according to FIG. 1
• d) Thin layer chromatogram: R _f value: 0.9 (mobile phase: n-butanol / methanol / water in a volume ratio of 75: 20: 5; spraying agent: real blue salt B)
• e) Chemical reaction: For example, by boiling with sodium hydroxide solution 10% by weight Sodium hydroxide solution escapes ammonia and there remains a connection which all reactions one Amino sugar results, back.
• f) Analysis: N = 3.9%, C = 46.5%, H = 7.3%, O = 42.3%.
  So that formula N ₂ C ₂₄ H ₅₄ O ₂₄ .

II)

As the extraction residue from the extraction of the syrup with tetrahydrofuran 5 g (0.5% of theory) of one obtained non-crystalline, resinous material. There were 3 compounds, of which 2 the reactions of an amino sugar, determined.

• a) IR spectrum according to FIG. 2.
• b) Thin layer chromatogram: R _f values of R _{f 1} = 0.12 yellow
  R _{f 2} = 0.18 blue and
  R _{f 3} = 0.34 blue (mobile solvent: n-butanol / methanol / water in a volume ratio of 75: 20: 5; spray reagent: ninhydrin).
• c) Analysis: N = 3.6%, C = 37.6%, H = 7.1%, O = 51.7%.

Claims (7)

1.) Plant extracts from Mesembryanthemaceae, namely

• I) viscous liquids,
  obtainable by pressing out the green parts of the plants and filtering the press juice, then concentrating the press juice, precipitating with sulfuric acid, filtering off the precipitate, washing it with water and making the filtrate combined with the wash water or wash water alkaline to an pH value of with an alkaline solution at least 10.2 and subsequent separation of the liquid from the precipitate and evaporation at a temperature not exceeding 100 ° C / normal pressure up to the syrup-like consistency and extraction with tetrahydrofuran and evaporation of the solvent from the extract or
• II) non-crystalline resinous substances,
  obtainable by pressing out the green parts of the plants and filtering the press juice, then concentrating the press juice, precipitating with sulfuric acid, filtering off the precipitate, washing it with water and making the filtrate combined with the wash water or wash water alkaline to an pH value of with an alkaline solution at least 10.2 and subsequent separation of the liquid from the precipitate and evaporation at a temperature not exceeding 100 ° C / normal pressure up to the syrup-like consistency and extraction with tetrahydrofuran and separation of the residue of the extraction

2.) Plant extracts according to claim 1 I), characterized in that they from Mesembryanthemum edulis (Carpobrotus edulis)

• a) with a boiling point of 165 to 168 ° C / normal pressure,
• b) with a refractive index of n = 1.4628.
• c) with an IR spectrum according to FIG. 1,
• d) with a thin-layer chromatographic R _f value of 0.9 (mobile phase: n-butanol / methanol / water in a volume ratio of 75: 20: 5; spray reagent, real blue salt B) and
• e) with a chemical reaction by boiling with sodium hydroxide solution with the escape of ammonia to a compound which gives all the reactions of an amino sugar.

are. 3) Plant extracts according to claim 1 II), characterized in that they from Mesembryanthemum edulis (Carpobrotus edulis)

• a) with an IR spectrum according to FIG. 2 and
• b) thin-layer chromatographic R _f values of R _{f 1} = 0.12 yellow,
  R _{f 2} = 0.18 blue and
  R _{f 3} = 0.34 blue (mobile solvent: n-butanol / methanol / water in a volume ratio of 75: 20: 5; spray reagent: ninhydrin)

are. 4.) Pesticides, characterized by Containing 1 or more plant extract (s) according to claim 1 I) or 2 and optionally Claim 1 II) or 3 as the active ingredient (s), if appropriate together with 1 or more common pest control compounding agent (s). 5.) Medicinal products characterized by a content 1 or more plant extract (s) according to claim 1 to 3 as the active ingredient (s), if appropriate along with 1 or more common pharmaceutical Packaging agent (s).