DE2921401A1 - Antibiotic with herbicidal and fungicidal activity - esp. obtained by culturing new Streptomyces griseus strain - Google Patents

Abstract

New antibiotic (I) is obtd. by culturing microorganisms of the order Actinomycetales, esp. the new strain Streptomyces griseus 587 (DSM 1471). (I) is characterised by its physicochemical properties: (1) IR absorption at 3400 2920, 1680, 1375, 1260, 1140 and 825 cm-1 (KBr); (2) elementary analysis C 63.2%, H 8.0%, N 4.7%, O 24.1% by difference); (3) optical rotatory dispersion spectrum with lambda max = 297 nm (+380 degrees, c=3 mg/10 ml CHCl3); (4) mass spectrum with fragment-ion peaks at 260, 205, 155, 152, 126, 112, 84, 69, 55 and 41. (I) is useful as a defoliant, desiccant, germination inhibitor and esp. herbicide active against mono- and dicotyledonous plants (pre- and post-emergence herbicidal activity against Lepidium sativum is exemplified). (I) also has fungicidal activity e.g. with MIC values of =1.0 against Pyricularia, Pellicularia and Sclerotinia spp. and yeasts.

Description

Organic-chemical compound, microbiological

Method of manufacture and use thereof The present invention relates to an organic chemical compound, microbiological process for its Production and their use as crop protection agents, especially as herbicides.

The connection according to the invention can be represented by that shown in FIG IR-KBr absorption spectrum (abscissa: wave number in cm 1, ordinate: absorbance), the characteristic band at wave numbers 3400, 2920, 1680, 1375, 1260, 1140 and 825 cm 1.

Furthermore, the compound can have the following properties and parameters are described: (1) Elemental analysis C: 63.2% H: 8.0% N: 4.7 % Ob: 24.1% + calculated from the difference (2) Decomposition point The substance forms a white amorphous powder with a decomposition point of 120 - 12500.

(3) ORD spectrum The ORD spectrum of the substance shows a maximum at 297 nm (+ 3800, c = 3 mg in 10 ml of chloroform) (4) Ultraviolet absorption spectrum The compound shows no absorption in the range from 350 nm to 200 nin.

(5) 1H-100 MEIz nuclear magnetic resonance spectrum The characteristic 1H NMR spectrum is shown in FIG.

(6r mass spectrum (according to FIG. D) In the mass spectrum there is a molecular ion not observed. Characteristic fragment ions appear at 263, 205, 204, 155, 152, 126, 112, 84, 69, 55 and 41.

(7) The compound is soluble in methanol, ethanol, ethyl acetate, Butyl acetate, benzene, acetone and chloroform, sparingly soluble in water.

(8) The compound according to the invention can be hydrolyzed under acidic conditions. For example, after 14 hours of treatment with 6N hydrochloric acid, 1100C in the hydrolyzate ammonium ions can be detected.

(9) The compound of the present invention is an amorphous colorless substance. It is easily possible to identify the compound in thin layer chromatography on a To color silica gel plate. Some of the reactions used for identification are listed in Table 1.

(10) The Rf values of the compound according to the invention on neutral pebble plates is given in Table 2.

(11) The antibiotic effect of the compound of the present invention is shown in Table 3.

Table 1: Experiments for the chemical staining of the compound no. Reagent / Reaction after +) staining 1 ninhydrin 2 Morgan / Elson 3 4-dimethylaminobenzaldehyde 4 KMnO4, alk. + 5 thymol / H2S04 + 6 anisaldehyde / H2S04 + 7 periodate 8 2,7-dichlorofluorescein 9 iodine + Table 1 (continued) No. reagent / reaction after +) staining 10 bromocresol green 11 rhodamine B 12 moybdatophosphoric acid + 73 aniline phthalate 14 Tollen's reagent 15 diphenylamine + 16 2,4-dinitrophenylhydrazine -17 iron (III) chloride - +) The reagents were determined according to the usual regulations (cf. E. Stahl, thin layer chromatography, 2nd edition, Springer-Verlag, Berlin-Heidelberg-New York, 1967).

Table 2: Thin-layer chromatographic characterization of the compound on silica gel 60, F 254, layer thickness 0.25 mm (Merck) superplasticizer system (parts by volume) Rf values n-butanol / glacial acetic acid / H20 = 50/25/25 0.60 chloroform / methanol / glacial acetic acid = 90/8/2 0.63 chloroform / methanol / H2O = 80/20 / 2.5 0.66 acetone 0.55 chloroform / methanol = 80/20 0.65 Table 2 (continued) Solvent system (parts by volume) Chloroform / methanol = 90/10 0.37 chloroform 0.05 diethyl ether 0.06 chloroform / methanol / ammonia = 20/3 / 0.5 0.62 n-butyl acetate / n-butanol / glacial acetic acid / phosphate buffer pH 7 = 50/10/25/15 0.62 i-propanol / 2 N ammonia / H2O = 7/1/2 0.71 methanol 0.64 Table 3: Antibiotic Effect of the compound according to the invention organism minimal inhibitory concentration µg / ml Yeast HT - 21 # 0.5 Yeast HT - 10 # 0.5 Sacharomyces cerevisiae 1.0 Pyricularia oryzae # 0.5 Pellicularia sasakii # 1.0 Sclerotinia sclerotiorum Botrytis cinerea L8.0 Xanthomonas oryzae> 1000 E. coli> 1000 The inventive Compound is obtained by combining microorganisms of the order Actinomycetales in one Nutrient medium, which contains assimilable carbon and nitrogen sources as well as mineral salts contains cultured under aerobic bonds and the compound is isolated.

To obtain the compound according to the invention are suitable within of the order Actinomycetales especially representatives of the family Streptomycetaceae and here mainly those from the genus Streptomyces. The inventive method can be carried out particularly well with microorganisms of the species Streptomyces griseus will. Streptomyces griseus strain 587 is mentioned as an example. This tribe became under the number DSM 1471 on February 23, 1979 at the German Collection of Microorganisms Göttingen deposited. Bacterial strains that are used to carry out the invention Method suitable can be from soil samples of terrestrial or marine origin can be isolated by the methods commonly used for this purpose. Streptomyces griseus strain 587, for example, could be enriched from a marine sediment sample be that with a grab in January 1968 in the North Sea off the Scottish Coast was taken from a depth of 63 m. The tribe has been around since that time on suitable solid culture media (e.g. on HPG agar: 3 g yeast extract, 6 g peptone, 10 g glucose, 8 g NaCl, 20 g agar, 1000 ml demineralized water, pH on 7.0 set) kept in culture.

Streptomyces griseus strain 587 has the following characteristics: a) Strain 587 forms the aerial mycelium typical of Streptomycetes with clearly defined spore chains. The spores are oval to cylindrical.

Dimensions: 0.4-0.8 / µm x 0.8-1.8 / µm. The spore surface is smooth or slightly structured.

b) The color of the young aerial mycelium is white. The mature aerial mycelium is yellow to sand-colored ("griseus").

c) The sporophores are sympodially branched and arranged in tufts. The spore chains are straight or wavy (rectus flexibilis ") and carry up to about 60 spores.

d) No dark pigment is formed on culture media containing peptones. The strain is therefore not chromogenic.

These characteristics show strain 587 (DSM 1471) as belonging to the species Streptomyces griseus Waksman et Henrici belonging from (based on Hütter, R .: Systematics of the Streptomycetes, Basel-New York, Karger 1967).

The inventive method can with the help of solid, semi-solid or liquid culture media. Aqueous-liquid nutrient media are preferred used.

The inoculation of the culture media is carried out according to generally accepted methods, e.g. via inclined tubes or flask cultures.

The culture takes place under aerobic conditions and can according to the general common methods as shake culture e.g. in shake flasks, as air-healed culture or as a submerged culture. The cultivation is preferably carried out in aerobic submerged processes in aerated fermenters, e.g. in conventional submerged fermentation tanks. It is possible to carry out the culture continuously or batchwise.

The process is preferably carried out batchwise.

The culture can be carried out in all nutrient media known to be used to cultivate microorganisms of the order Actinomycetales. The nutrient medium must have one or more assimilable sources of carbon and nitrogen as well as mineral salts, these products in the form of defined individual components, but also in the form of complex mixtures, such as those used in biological products in particular represent different origins, may be present. As carbon sources come all common carbon sources in question.

Examples are starch, molasses, whey powder, dextrin and sugar, such as sucrose, maltose, glucose, lactose, sorbitol and glycerin. As nitrogen sources all common organic and inorganic nitrogen sources are suitable. as Examples are soybean flour, cottonseed flour, lentil flour, pea flour, soluble ones and insoluble vegetable proteins, corn steep liquor, yeast extract, peptones and meat extract as well as ammonium salts and nitrates, e.g. NH4Cl, (NH4) 2504, NaN03 and KN03. The mineral salts that should be contained in the nutrient medium provide, for example, the following Ions: Mg ++, Na +, K +, Ca ++, NH4 +, Cl-, SO4--, PO4 --- and NO3- as well as ions of the usual ones Trace elements such as Cu, Fe, Mn, Mo, Zn, Co, Ni. In case the carbon or nitrogen sources or the water used does not contain sufficient amounts of these salts or trace elements, it is advisable to supplement the nutrient medium accordingly. The composition the nutrient media can be varied over a wide range. Type and composition the nutrient media will generally depend on which ingredients each are available particularly cheaply.

When carrying out the procedure, it can be beneficial to start at the beginning the cultivation only relatively low concentrations of the soluble nutrient solution components to use and then in the course of cultivation these components in the form of sterile, to feed relatively concentrated solutions to the culture batch in fractions.

The pH of the growing cultures should be between about 5.5 and about 9.5 are held. An excessive drop in pH in the acidic range can be caused by additives an organic or inorganic base, preferably CaCO 3, should be avoided. As usual in fermentation technology, an automatic pH control can also be used carried out using sterile organic or inorganic acids, e.g. H2S04, or sterile lye, e.g. NaOH, is injected into the culture solution at intervals.

It is useful to ensure that the microorganisms are sufficient be brought into contact with oxygen as well as the nutrients. This can be done after the generally customary methods such as shaking and stirring.

The growth temperature can be between about 10 and about 400Cr. The duration of the breeding can be varied widely, e.g. the composition the culture medium and the cultivation temperature play a role. The respective gene optimal conditions can be found by anyone skilled in the microbiological field can be easily set.

It has been found that the amount of the culture broth enriching compound according to the invention in general its maximum between the Reached 1st and 12th, preferably between the 2nd and 5th day after the start of cultivation.

As in general with microbiological procedures, foreign infections of the culture media are avoided. The usual precautions are taken for this purpose, such as sterilization of the culture media, the culture vessels and those necessary for ventilation Air. Steam as well as dry sterilization can be used to sterilize the devices be used.

If undesirable amounts of foam are produced during cultivation, the usual chemical foam suppressants, e.g. liquid fats and oils, oil-water emulsions, paraffins, higher alcohols such as octadecanol, silicone oil, polyoxyethylene respectively.

Polyoxypropylene compounds are added. Foam can also be used Using the usual mechanical devices (which e.g. use centrifugal forces) be dampened or eliminated.

The compound according to the invention can generally be obtained from the culture medium common physico-chemical methods can be isolated. The insulation can e.g. according to the usual extraction processes, precipitation processes and / or chromatography processes take place. The isolated herbicide can also be finely cleaned with the help of the methods mentioned will. In many cases, however, a fine cleaning is not necessary because the any impurities present reduce the effectiveness of the compound as a herbicide not adversely affect. During all isolation and cleaning operations care must be taken that pH values above pH 2 are maintained. To increase the pH, inorganic and organic bases can be used, e.g.

Ammonia, alkali and alkaline earth hydroxides, alkali and alkaline earth carbonates and hydrogen carbonates, e.g.

XOH, NaOH, Na2C03, NaHC03, CaC03, trialkylamines such as triethylamine, Morpholine and pyridine. To do with the above isolation and cleaning methods to find out the fractions in which the compound according to the invention is in the highest Concentration or purity is available, the usual physico-chemical Methods, e.g. measuring the Rf values, or investigating the herbicidal activity and preferably used to determine the antibiotic activity.

The isolation of the compound according to the invention can, for example, in the case that a liquid aqueous nutrient medium is used as follows be made: After its accumulation in the culture supernatant are culture filtrate and mycelium are separated using conventional methods (e.g. centrifugation).

The compound according to the invention can be extracted from the culture filtrate with the aid of of conventional extraction processes, precipitation processes and / or chromatography processes isolated and cleaned if necessary. The chromatography can be in the form of the Column chromatography can be carried out. The usual adsorbents can be used inorganic or organic adsorbents are used, such as aluminum oxide, Silica gel, magnesium silicate, activated carbon, cellulose, cellulose derivatives, synthetic resins such as polyamides, derivatives of polyamides, e.g. acetylated polyamide or dextran gels. A wide variety of solvents or solvent mixtures can be used as mobile solvents can be used in which the compound of the invention is soluble. Preferred methanol and ethanol are used.

Chromatography processes are preferred for isolating the compound according to the invention used, e.g.

unspecific adsorption on hydrophobic sorbents.

These are neutral natural substances that are poorly water-soluble from cleaning known methods.

Preferred for the commercial production of the herbicide according to the invention one obtaining by adsorption and subsequent desorption on a hydrophobic Carrier resin (e.g. Lewapol; a hydrophobic carrier resin from BAYER AG). The desorption can e.g. be carried out with short-chain aliphatic alcohols, preferred Methanol or ethanol.

Such a pre-purified fraction can in turn with the usual Methods to be cleaned. Gel diffusion chromatography can be preferred here can be used. The chromatography, for example, runs on Sephadex LH-20 successfully. It is preferable to work in an alcoholic solution here. One of those The product obtained is generally purer than 50 as.

The compound according to the invention can from such a fraction with can be obtained using the usual biochemical methods. Of the adsorbents already mentioned In addition to others, silica gel in particular can be used successfully. As a superplasticizer For example, chloroform-methanol (about 4/1 parts by volume) is successfully used.

From its solutions, the connection can be made according to the usual methods, e.g., evaporation of the solvent, freeze-drying, etc. can be obtained.

The active ingredient according to the invention influences plant growth and Can therefore be used as a defoliant, desiccant herbicide, sprout inhibitor una are used in particular as weed killers. Under weeds in In the broadest sense, all plants are to be understood that grow in places where they are are undesirable. Whether Gie substances according to the invention as total or selective herbicides act depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in the following plants are used: Dicot weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cuburbita.

Monocot weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monocharia, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dadyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

However, the use of the active ingredients according to the invention is by no means limited to these genera, but extends in the same way to other plants.

The compounds are suitable depending on the concentration for total weed control e.g. on industrial and rail systems and on paths and Places with and without trees. Likewise, the compounds can be used for weed control in permanent crops e.g. forest, ornamental wood, fruit, wine, citrus, nut, banana, Coffee, tea, rubber, oil paim, cocoa, berry fruit and hops plants and for selective weed control can be used in annual crops.

The active compounds according to the invention can be used as such or in their formulations can also be used in a mixture with known herbicides for weed control, finished formulation or tank mixing is possible.

The active ingredient can be converted into the usual formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, Pastes, soluble powders, granulates, aerosols, suspension emulsion concentrates, Seed powder, active ingredient-impregnated natural and synthetic substances, ultra-fine encapsulation in polymeric substances and in coating compounds for seeds, furthermore in form mulations with burning sets, such as incense cartridges, cans, spirals, etc. as well as ULV cold and Warm mist formulations.

These formulations are prepared in a known manner, for example by Mixing the active ingredient with extenders, i.e. liquid solvents, under Liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In the case of using water as an extender For example, organic solvents can also be used as auxiliary solvents. The following liquid solvents are essentially: aromatics, such as xylene, Toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. petroleum fractions, alcohols such as butanol or Glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; with liquefied gaseous extenders or carriers such liquids are meant which are at normal temperature and under normal pressure are gaseous, e.g. aerosol propellants such as halogenated hydrocarbons as well Butane, Propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as fumed silica, alumina and Silicates; as solid carriers for granules: broken and fractionated natural Rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granulates made from inorganic and organic flours and granulates made from organic material such as sawdust, coconut shells, corn cobs, and tobacco stalks; as emulsifying and / or foam-generating agents: non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, Polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolysates; as a dispersant: e.g. Lignin sulphite liquors and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-like polymers are used such as gum arabic, polyvinyl alcohol, polyvinyl acetate.

Dyes such as inorganic pigments, e.g.

Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as Alizarin, azo metal phthalocyanine dyes and trace nutrients such as iron salt, Boron, copper, cobalt, molybdenum and tin can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

Example 1 Inoculate a 1 1 Erlenmeyer flask containing 150 ml of a Nutrient solution of the composition 0.5% (NH4) 2S04, 0.3% KNO3, 0.4% soy flour, 0.4 % Corn steep liquor, 6.0% starch, 0.5% CaC03 (pH adjustment before sterilization on 7.0 with KOH, sterilization 20 minutes at 121 ° C.) contains 3 ml of a preculture des Strain 587 (obtained in the same nutrient solution, inoculated with an inclined tube culture) and incubate this culture at 280C on a rotary shaker at 280 rpm, see above after a culture period of 3 days, a culture broth is obtained, the content of which is Active ingredient according to Example 9 is determined to be 32 mg / l.

Example 2 Inoculate a 1 1 Erlenmeyer flask containing 150 ml of a Nutrient solution containing 2% starch, 1% glucose, 0.5% N-Z amines, 1.0% yeast extract, adjust their pH to 7.2 with Na2CO3 and then add 0.4% CaCO3 and had been sterilized for 30 minutes at 121oC, with 3 ml of a preculture of the strain 587, obtained in the same nutrient solution and incubated on a rotary shaker at 280 ° C. and 280 rpm, a culture broth is obtained after 2 days, the content of which of active ingredient according to Example 9 is determined to be 4 mg / l.

Example 3 Inoculate a 1 1 Erlenmeyer flask containing 150 ml of a Nutrient solution made from 3% soy flour defatted, 3% glycerine, 0.2% CaCO3, 0.1% polyol defoamer and had been sterilized at 121 ° C. for 30 minutes, a preculture with 3 ml of strain 587 obtained in the same nutrient solution and incubated at 280C on one Rotary shaking machine at 280 rpm, a culture broth is obtained after 3 days Content of active ingredient according to Example 9 is determined to be 8 mg / l.

Example 4 Inoculate a 1 1 Erlenmeyer flask containing 150 ml of a Nutrient solution of 3% starch, 2% yeast autolysate, 0.1% K2HP04, 0.1% MgS04 7H20, 0.1 % NaCl, 0.2% (WH4) 2S04 and 0.2% CaCO3, the pH of which is adjusted to 7.0 and which had been autoclaved for 30 minutes at 121 0C, with 3 ml of a preculture, obtained in the same nutrient solution, and incubated on a rotary shaker 28 ° C. and 280 rpm, a culture broth is obtained after 3 days, the content of which is Active ingredient according to Example 9 is determined to be 4 mg / l.

Example 5 A fermenter is inoculated with 200 l of a nutrient solution contains according to Example 1, with 10 1 of a preculture obtained in a pre-fermenter of the strain 587 and incubated with stirring (200 rpm) and aeration (0.5 vvm) for 5 days at 280C, a culture broth is obtained, the content of active ingredient according to example 9 is determined to be 128 mg / l.

Example 6 In a fermentation according to Example 5 are after Centrifugation 170 1 culture filtrate obtained. The culture supernatant is at 50 l / h onto a column (30x50 cm) containing a hydrophobic sulfonic acid-based carrier resin (e.g. Lewapol) is applied and the column is washed with 100 1 H20. Pass and wash water are not herbicidally effective and are discarded. Then will first desorbed with 100 1 50 96 dem methanol.

The inactive desorbate is discarded. Subsequent desorption with 100 1 100 96dem methanol leads to a herbicidally effective eluate. The eluate will concentrated to dryness, the residue thus obtained was taken up in 2 l of water and the suspension is lyophilized (yield 40.2 g 3.5% but active ingredient).

Example 7 4.0 g of the 3.5% strength active ingredient according to the example are dissolved 6 in 50 ml of methanol, centrifuged off and the supernatant chromatographed on Sephadex LH-20 in methanol (column 5 cm x 100 cm, flow rate 100 ml / h, 12 '/ glass). The factions 75-78 show inhibitory effects against the yeast HT-21 and are also herbicidal (yield 119 mg). According to Example 9, the active ingredient content can be determined to be approx. 50%.

Example 8 100 mg of enriched preparation according to example are dissolved 7 in 5 ml of chloroform / methanol = 5/1 (v / v) and carries linear shaped onto a preparative 2 mm thick silica gel plate (KG 60, Merck). It will be with eluted with the specified solvent. The zone with an Rf value of 0.55 to 0.75 is eluted with methanol and contains 27.7 mg of the pure active ingredient.

Example 9 From a solution of 1 mg / ml of the pure active ingredient according to Example 8, the inhibitory potency against the yeast HT-21 is determined in the hole test. Included After 12 hours of incubation at 280C, the diameter of the inhibition zone is dependent measured by the concentration.

1 mg / ml undiluted 1: 1 1: 4 1: 8 1:16 active substance 0 inhibition zone mm 59 49 45 43 42 1:32 1:64 1: 128 1: 256 1: 512 1: 1024 1: 2048 1: 4096 40 35 30 2? 19 14 12 - By Determination of the minimum inhibitory concentration of the preparations of Examples 1 to 8 could therefore the active ingredient content can be determined.

Example 10 pre-emergence test In bowls filled with vermiculite are, will Cress seeds (Lepidium sativium) laid out. the Bowls are then poured with a Hoagland nutrient solution containing the present invention Active ingredients are added.

After 2 weeks, the degree of damage to the plants is rated in% Damage compared to the development of the untreated control.

The preparations according to the above examples show a high level of effectiveness.

Example ii post-emergence test In bowls filled with vermiculite are, seeds of cress (Lepidium sativum) are laid out. The shells will then watered with a Hoagland nutrient solution until the plants reach a size of 5 to 10 cm.

The plants are then sprayed with an active ingredient preparation.

After 2 weeks, the degree of damage to the plants is rated in% Damage compared to the development of the untreated control.

The preparations according to the above examples show a high level of effectiveness.

Example 12 Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether, Wst: active ingredient for production 1 part by weight of active ingredient is mixed with an appropriate active ingredient preparation the specified amount of solvent, adds the specified amount of emulsifier and dilutes the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil and after Doused with the active ingredient preparation for 24 hours. You keep the amount of water expediently constant per unit area. The active ingredient concentration in the Preparation does not matter, only the application rate of the active ingredient is decisive per unit area.

After 3 weeks, the degree of damage to the plants is rated in% Damage compared to the development of the untreated control. It means: 0% = no effect (like untreated control) 100% = total destruction The active ingredient according to the invention has this test compared to the prior art clear advantages.

Example 13 Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether Active ingredient preparation is mixed 1 part by weight of active ingredient with the specified Amount of solvent, add the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

Test plants which have a Height of 5 to 15 cm have such that the amounts of active ingredient given in the table can be applied per unit area. The concentration of the spray liquor will be like this chosen that the amount of active compound stated in the table was applied in 2,000 1 of water / ha will. After 3 weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means: 0% = none Effect (like untreated control) 100 9s = total destruction in this test the active ingredient according to the invention has clear advantages over the prior art on.

Claims (1)

Claims 1) Organic chemical compound appearing in the IR-KBr absorption spectrum characteristic volumes with wave numbers 3400, 2920, 1680, 1375, 1260, 1140 and 825 cm-¹, in the elemental analysis a carbon content of 63.2%, a hydrogen content of 8.0%, a nitrogen content of 4.7% and an oxygen content, calculated from the difference of 24.1% shows a maximum at 297 in the ORD spectrum mm (+ 380 °, c = 3 mg in 10 ml chloroform) and characteristic in the mass spectrum Has fragment ions at 2o3, 205, 204, 155, 152, 126, 112, 84, 69, 55 and 41. 2) A method for producing a compound according to claim 1, characterized characterized in that microorganisms of the order Actinomycetales, in a nutrient medium, which contains assimilable carbon and nitrogen sources and mineral salts cultured under aerobic conditions and the compound isolated. 3) Method according to claim 2, characterized in that one microorganisms of the family Streptomyceraceae kultlvert. i, The method according to claim 2, characterized in that one Microorganism of the genus Streptomyc - s cultivated. 5 ', method according to claim 3, characterized in that Streptomyces griseus strain 587 (DSM 1471). 6) Herbicidal agent containing a compound according to claim 1. 7) use of a compound according to claim 1 for combating unwanted plant growth. 8) Method of combating unwanted plant wax, thereby characterized in that a compound according to claim 1 on the plants and / or allows their living space to act. 9) Process for the preparation of a herbicidal agent, characterized in that that a compound ge-3 claim 1 with extenders and / or surface-active Means mixed up. 10) Microorganisms of the order Actinomycetales that occur during cultivation in a nutrient medium containing carbon and nitrogen sources and mineral salts produce a compound according to claim 1. 11) microorganisms according to claim 10 of the family Streptomycetacetaceae. 12) Microorganisms according to claim 10 of the genus Streptonyces 13) Streptomyces griseus strain 587 (DSM 1471). 1 culture containing a microorganism according to claims 10 to 13 contains. 15) Using microorganisms in making a compound according to claim 1.