EP2538782A2 - Agent phytoprotecteur - Google Patents

Agent phytoprotecteur

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Publication number
EP2538782A2
EP2538782A2 EP11705425A EP11705425A EP2538782A2 EP 2538782 A2 EP2538782 A2 EP 2538782A2 EP 11705425 A EP11705425 A EP 11705425A EP 11705425 A EP11705425 A EP 11705425A EP 2538782 A2 EP2538782 A2 EP 2538782A2
Authority
EP
European Patent Office
Prior art keywords
juglans
compound
pterocarya
plant
juglone
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.)
Withdrawn
Application number
EP11705425A
Other languages
German (de)
English (en)
Inventor
Karl Stich
Thilo Fischer
Christian Gosch
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.)
Technische Universitaet Wien
Original Assignee
Technische Universitaet Wien
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 Technische Universitaet Wien filed Critical Technische Universitaet Wien
Publication of EP2538782A2 publication Critical patent/EP2538782A2/fr
Withdrawn legal-status Critical Current

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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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N43/08—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 with oxygen as the ring hetero atom
    • 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
    • A01N43/14—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 six-membered rings
    • A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]

Definitions

  • the present invention relates to a crop protection agent for controlling bacterial and / or fungal infections in plants.
  • Copper-based preparations are also active, but are increasingly restricted to prevent copper accumulation in the soil.
  • nanoscale silver can also be used to combat Erwinia amylovora, which can potentially be accumulated in the soil as an element comparable to copper.
  • antagonistic bacteria are used in the flowering against fire blight, but do not achieve the efficiency of streptomycin.
  • Arbutin hydroquinone glucoside
  • GB 2 159 056 discloses naphthoquinones which are suitable for use in biocides.
  • compositions which can be used to inhibit nematode damage in plants. These compositions include extracts of juglone-producing plants.
  • the compositions described in WO 2006/060582 include juglone at a minimum concentration of 1000 ppm (1 g / L). At these concentrations, phytotoxic effects may occur in plants, especially in crops.
  • CN 1 781 376 relates to plant extracts which are suitable to be used as pesticides. These extracts are obtained from plants comprising juglone.
  • compositions disclosed in this document include naphthalenedione.
  • EP 1 051 909 relates to naphthoquinones which are suitable for combating pests.
  • WO 2000/56140 discloses methods and compositions for combating pests which occur in the water. These agents include, in particular, juglone and juglone analogs.
  • JP 4 295 402 discloses jugglucose glucosides.
  • the agents described in the prior art for controlling bacterial and fungal infections, in particular for combating Erwinia amylovora, or Erwinia infections, has a number of disadvantages. Many of the substances used can be harmful to animals and humans. On the other hand, other substances have a too low activity against fungi or bacteria, such as Erwinia, so that the economy is no longer given by an increased use of active ingredients and the environment is more heavily polluted.
  • the present invention relates to the use of a compound according to the formula (A)
  • R 1, R 4 and R 5 are independently H, a glycoside or an ester, as a pesticide, wherein the pesticide comprises the compound dissolved in a solvent at a concentration of 0.1 ⁇ M to 2 mM.
  • the compound is 5-hydroxy-1,4-naphthoquinone, 1,4,5-trihydroxynaphthalene and / or glycosides or esters thereof.
  • the present invention also relates to a crop protection agent comprising at least one compound of the general formula (I) or formula (I I):
  • R 1, R 4 and R 5 independently of one another are a glycoside radical, an added aldehyde, an added ketone, an organic acid radical, an inorganic acid radical or an aliphatic radical, and R 2, R 3, R 6, R7 and R8 are independent of each other which is a halogen or hydrogen, and addition products of S- and N-containing compounds to compounds of general formula II and polymers of both formulas and their respective derivatives in a concentration of 0.1 ⁇ to 2 or 5 mM.
  • Juglone is a substance that has been extensively studied for its phytotoxic ("allelo-pathic") effect, especially on seedlings.
  • the native walnut tree (Juglans regia) and other Juglandaceae prevent in a natural process the emergence of competing plant growth at their location.
  • the precursor 1, 4, 5-trihydroxynaphthalene-glucoside is formed. This is washed out of the leaves by precipitation and released via the roots and hydrolyzed in the soil by microbial glucosidases to 1,4,5-trihydroxynaphthalene. This is then oxidized to the active substance juglone (Weiler and Nover 2008). However, juglone can damage or kill even neighboring woody plants by their cumulative effect.
  • Juglon proves to be active (more effective than other quinones, including 1, 4-naphthoquinones such as plumbagin) against Erwinia, especially Erwinia amylovora.
  • the combination of low application concentrations with a time-limited application period represents the potential of juglone and its derivatives as plant protection products according to the invention against Erwinia amylovora.
  • the plant protection agent may also comprise interme ⁇ diary oxidation states of the compounds according to the invention, such as eg Juglon as semiquinone radical.
  • the glycoside residue is a glucosyl, mannosyl, galactosyl, fructosyl, ribosyl, arabinosyl, rhamnosyl or xylosyl residue.
  • the added aldehyde or ketone of the compound of the invention preferably contains 1 to 6 carbon atoms.
  • the remainder of the organic acid is selected from the group consisting of a formyl, acetyl, propionyl, butyryl, isobutyryl, malonyl, pyruvoyl, succinyl, 2-oxo-glutaroyl , Oxaloacetic, fumaric, tartaric and citric acid groups.
  • the remainder of the inorganic acid is preferably a phosphoric acid or sulfuric acid radical.
  • the remainder of the ethers is preferably a methyl or ethyl radical.
  • the halogen is preferably iodine, bromine, chlorine or fluorine.
  • the compound of the invention may also be present as a 1,2- or 1,4-addition product of the quinone form (formula II).
  • the compound of the invention can also be used as a polymer present and develop a corresponding antimicrobial activity.
  • the polymer is preferably 3,3 'bijuglon or cyclobutrolone.
  • the plant protection agent according to the invention may comprise the compounds in synthetic form but also in the form of a plant extract.
  • These extracts are preferably selected from the foliage or nuts of the walnut Juglans regia (or other Juglandaceae, Juglans ailanthifolia (syn. J. sieboldiana), J. cathayensis (syn. J. draconis), J. cinerea, J. hindsii, J. microcarpa (syn.
  • the compounds according to the invention additionally have the advantage that they are also useful for insects, e.g. Bees, harmless, i. not eating and contact poison, are. Many crop protection agents used to date against Erwinia infections do not have this benefit and are detrimental to beneficial insects.
  • the compounds of the invention in a concentration of 0.5 ⁇ M to 4 m or 0.5 ⁇ M to 1.5 mM, preferably from 1 ⁇ M to 1 or 2 mM, more preferably from 5 ⁇ M to 0.5 or 1 mM.
  • the compounds according to the invention are preferably dissolved in an aqueous and / or organic solvent in order to achieve the concentration required according to the invention in the crop protection agent.
  • the solvents used may include, but are not limited to, water or other organic solvents such as alcohols such as ethanol.
  • the compounds according to the invention can be dissolved, for example, first in an alcohol such as ethanol and then diluted in water or another aqueous medium for the production of pesticides to the concentration according to the invention.
  • buffer substances and the same may be present, which are usually added to crop protection agents.
  • the crop protection agent according to the invention can be used particularly well for controlling Erwinia amylovora in crop plants.
  • Exemplary crops, which are frequently attacked by Erwinia amylovora come mainly from the family Rosaceae. Particularly vulnerable is the subfamily of pome fruit (Maloideae). In the wood of pome fruits Erwinia amylovora is also able to overwinter.
  • the plant protection agent according to the invention in rose plants, preferably in pome fruit plants, in particular in apples of the cultivars Berlepsch, Braeburn, Cox Orange, Granny Smith, Elstar, Fuji, Gala, Gloster, Gravensteiner, Idared, James Grieve, Jonagold Group, Jonathan , White Clematis, Topaz and Vista Bella, and pears of the varieties Abbate Fetel, Conference, Williams Christ,instadechants, Gellerts Butterbirne, Harrow Sweet, Clapp's Darling, Comice, Concorde, Early of Trevoux, Gute Luise, Bosc's swipenbirne (Kaiser Alexander) To use Pastoren pear and Passa Crassana the.
  • ornamental shrubs such as quince, medlar, vetchling, wild berry, rowanberry / rowanberry, apple berry, ornamental quince, hawthorn like hawthorn and hawthorn, loquat, dwarf medlar and stingwort may also be treated with the plant protection product according to the invention to produce Erwinia amylovora to fight on these plants.
  • Erwinia amylovora can be combated particularly well with the plant protection agent according to the invention.
  • the plant protection product is also useful for controlling other Erwinia species which are effective as plant pathogens. These include Erwinia carotovora (causing blackleg in potato plants and wet rot in potato tubers), Erwinia billingia and Erwinia cypripedii.
  • the substances 5-hydroxy-l, 4-naphthoquinone (juglone) or 1, 4, 5-trihydroxynaphthalene can be obtained in various ways.
  • both substances can be produced synthetically by known chemical methods
  • both substances can be prepared from e.g. Leaves or nuts of Walnut Juglans regia (or other Juglandaceae) are extracted (e.g., with ethanol or an azeotropic water-ethanol mixture in a Soxhlet apparatus).
  • the synthesis of the derivatives according to the invention can also be carried out by known processes (for example by chromate oxidation of 1,5-dihydroxynaphthalene).
  • the “derivatives" of 5-hydroxy-1,4-naphthoquinone and 1,4,5-trihydroxynaphthalene are "selected from the group consisting of glycosides, hemiacetals, full acetals, esters, ethers, polymers and 1,2- or 1,4 Addition products and halogen-ring-substituted derivatives ".
  • the term "derivative" in the context of the present invention exclusively includes substances derived from 5-hydroxy-l, 4-naphthoquinone and 1,4,5-trihydroxynaphthalene and their hydroxy or keto groups glycosidated, esterified , etherified, acetalated, polymerized, added to other molecules or their ring systems are halogenated.
  • a particularly preferred derivative is the 1,4,5-trihydroxynaphthalene-4-glucoside incorporated in leaves and fruits of the walnut tree.
  • 4,5-trihydroxynaphthalene-4-glucoside is enzymatically or chemically cleaved off its glucose residue and the cleavage results in the chemical compound 1,4,5- Trihydroxynaphthalene ("Hydrojuglon"). From this, after an oxidation reaction, the substance forms juglone (5-hydroxy-l, 4-naphthoquinone).
  • the plant protection composition comprises 1, 4, 5-trihydroxynaphthalene or 1, ( 5-trihydroxynaphthalene-4-glucoside, both 1,4,5-trihydroxynaphthalene and 1,4,5-trihydroxynaphthalene-4 glucosides are converted to 5-hydroxy-1,4-naphthoquinone over time after application to the plant, this has the advantage that the plant's effect on Erwinia, for example, lasts longer, since 5-hydroxy-1, 4-naphthoquinone is released gradually.
  • active ingredients can be dissolved directly in water, or in a Pre-dissolved in organic solvent (preferably ethanol) and diluted in water before use, or, in a particularly preferred embodiment, are 1, 4, 5-trihydroxynaphthalene-4-glucoside, 1, 4, 5-trihydroxynaphthalene, 5-hydroxy-l , 4-Naphthoquinone or mixtures thereof (influenced by the nature of the isolation) from Juglandacea plant material, especially foliage of Juglans or Carya species, isolated and used as a dilute plant preparations.
  • Another possible source of juglone is Penicillium diversum or related organisms.
  • the crop protection agent of the present invention may comprise surfactants which do not undergo bactericidal chemical reactions with quinones (e.g., Tween 20 (0.005-0.1% by volume), but also surfactant natural substances).
  • the plant protection agent according to the invention particularly preferably comprises Na and K soaps, or commercial wetting agents, e.g. Agrowax 010, Break thru, Citro ⁇ n, Excellent CS 7, Neo-Bet, Agronetz, Ajutol, Silwet top, Zellx CS.
  • a further aspect of the present invention relates to the use of 5-hydroxy-1,4-naphthoquinone, 1,4,5-trihydroxynaphthalene and / or derivatives or esters thereof selected from the group consisting of glycosides, hemiacetals, acetals, esters, ethers, Polymers, 1,2- or 1,4-addition products as well as halogen-ring-substituted derivatives as pesticides.
  • the plant protection agent according to the invention is particularly preferably used for combating Erwinia, preferably Erwinia amylovora.
  • Another aspect of the present invention relates to a method for controlling bacterial and / or fungal infections, preferably Erwinia infections, in particular Erwinia amylovora infections, in plants comprising the step of applying a plant protection agent as defined herein to flower and / or foliage the plants.
  • the plant protection agent disclosed herein can be applied to the flower and foliage of the plants to be treated by methods known in the art. Usually, the application of pesticides by spraying, spraying or dusts.
  • the plant protection agent As the primary infection in pome fruit is usually due to the flowering of bees, especially when humid weather conditions conditions prevail, it is particularly preferred at this time to use the plant protection agent according to the invention. Due to the short-term application during the flowering of the flowers, cumulative phytotoxic effects on the fruit trees are avoided in this embodiment.
  • the crop protection agent 5-hydroxy-l, 4-naphthoquinone (juglone) according to the invention has proved to be non-edible or contact-poisonous for bees in investigations carried out on behalf of the company.
  • the plant protection agent according to the invention is preferably applied to the plant in the twilight, ie reduced UV irradiation, or in the dark.
  • Yet another aspect of the present invention relates to a process for the preparation of a crop protection composition
  • a crop protection composition comprising a compound of the formula (A)
  • R 1, R 4 and R 5 are independently H, a glycoside or an ester comprising the step of dissolving the substantially crystalline compound of the general formula (A) or (B) in a solvent in a concentration of 0.1 ⁇ M 2 mM or adjusting or diluting a plant extract comprising the compound of the general formula (A) or (B) such that the plant protection agent comprises the compound in a concentration of 0.1 ⁇ to 2 mM.
  • the compounds of the invention may be formulated inter alia by dissolving in a solvent to a crop protection agent.
  • the plant protection agent according to the invention can be prepared in a simple manner in the required concentration range in which the weighed amount of the compounds according to the invention is mixed with an appropriate amount of solvent. If compounds according to the invention are part of a plant extract, the amount of the compounds according to the invention present in this extract is first determined in order subsequently to dilute the extract with a solvent or to add it to further compounds of the invention in solid or liquid form.
  • the compound is 5-hydroxy-1, 4-naphthoquinone, 1, 4, 5-trihydroxynaphthalene and / or glycosides or esters thereof.
  • Another aspect of the present invention relates to a crop protection agent obtainable by a process of the present invention.
  • Fig. 1A to 1D shows growth inhibition (cell density measured as optical density at 600 nm) by juglone and comparative plumbagin on suspension cultures of Erwinia amylovora: Top: the 1, 4-naphthoquinone juglone 0.01 / 0.05 / 0.1 mM, Control with equal volume of the solvent ethanol, and control with pure KB medium. Second graph: repetition with 0.01 mM juglone and lower concentrations (0.005 / 0.001 mM). Third graph: 0.1 and 1 mM plumbagin (the initial change in absorbance at 1 mM plumbagin is caused by a reaction with the medium). Fourth chart: Positive control with the conventional herbicide streptomycin (antibiotic) used against Erwinia amylovora.
  • Figure 2 shows the growth inhibitory effect of 0.05 and 0.1 mM juglone on Erwinia carotovora.
  • E Control with equal volume of the solvent ethanol
  • K Control with pure KB medium.
  • Fig. 3 shows pear inoculation assays by preincubation with various concentrations of juglone (and streptomycin as control) and subsequent (15 min) inoculation with Erwinia amylovora. Image after 6 days incubation at 25 ° C. Culture plate as a control for the vitality of Erwinia amylovora cells used.
  • Fig. 4 shows the results of a study comparing the effect of representatives of three classes of quinones against Erwinia amylovora.
  • 1,4-naphthoquinones were evaluated to assess their potential as crop protection agents.
  • the 1,4-naphthoquinones juglone (5-hydroxy-1,4-naphthoquinone) and plumbagin (5-hydroxy-2-methyl-1-naphthoquinone) were tested for their activity against Erwinia amylovora and Erwinia carotovora.
  • the growth curves of the suspension cultures in the presence of various juglone concentrations demonstrate an inhibition of the growth of Erwinia amylovora.
  • these experiments give no information about the nature of the underlying effect, which could be bacteriostatic (inhibition of growth, no direct killing of cells) or bactericidal (killing of cells).
  • this can be ascertained by plating out aliquots of the suspension cultures with active ingredient on active substance-free solid media. On such solid media, the drug is diluted from the small volume aliquot by diffusion below a threshold such that, if cells were only inhibited but not killed, colonies form after incubation.
  • Such plating tests were performed with 0.1 mM juglone in the suspension culture by taking aliquots in a time series.
  • the control was a culture containing a corresponding volume of the solvent for the Glon (ethanol) had been added.
  • a repeat of the experiment with only 0.01 mM juglone was also performed, with serial dilutions for the respective aliquots for accurate titer determination. Only for the time points immediately after addition of juglone colony formation could be observed in both test series, after each longer incubation (after 30 min) no colony formation from surviving cells took place.
  • Juglone has a strong bactericidal effect on Erwinia amylovora.
  • Erwinia carotovora was selected as an example of another Erwinia species.
  • the effect of 1, 4-naphthoquinone juglone on the growth of Erwinia carotovora in suspension culture was tested by the same methodology as in the case of Erwinia amylovora.
  • Juglone also has a growth-inhibiting effect on other Erwinia species in suspension culture, but at least for Erwinia carotovora this effect is weaker than for Erwinia amylovora.
  • Juglone was tested in in vitro infection tests with apple blossoms, as well as comparing the 1,4-naphthoquinone plumbagin and 1,4-benzoquinone. Streptomycin was used as a positive control.
  • Table 1 In vitro infection tests on apple blossoms (Malus x domestica) with juglone as well as plumbagin and 1, 4-benzoquinone. Streptomycin as a positive control.
  • Juglone has good potential as an agent to control primary fire blight (flower infections).
  • necrotic lesions of the plant tissue and the formation of white bacterial mucus were used as criteria for assessing the extent of Used infection. Necrotic lesions were observed in the experiment on both varieties (Williams Christ and Bosc's swipenbirne), while exudate formation was observed only in the Williams Christ variety. Although necrotic lesions were observed in both strains for the 0.01 mM low concentration of streptomycin in the positive control, these were somewhat reduced compared to inoculation with Erwinia amylovora without the antibiotic, and there was no exudate formation.
  • 0.1 mM juglone showed approximately the same effect as 0.01 mM streptomycin in this system.
  • juglone and comparative plumbagin were tested on flowers of two apple varieties (Smoothy, a Golden Delicious offspring, and Idared) as well as a pear variety (Williams Christ) under growing conditions in a trellis tree planting for flowering. In each case, the concentrations were used, which had been found in the in vitro suspension cultures as fully effective (no bacterial growth). Various concentrations were tested (0.005-0.05 mM juglone and 0.1-0.5 mM plumbagin) (Table 2). Control treatments with water and with the ethanol concentrations used in the drug solutions (0.5 and 5%, to pre-dissolve the active ingredients) were performed and showed, as expected, no effects.
  • Table 2 Overview of phytotoxicity to flowers rsp. Fruit development of apple and pear varieties tested concentrations of juglone and plumbagin.
  • Juglone is a well-known walnut biotactic compound (Juglans regia) (and other Juglandaceae), while plumbagin is from North American Drosera species (Drosera rotundifolia, Drosaceae), Plumbago species (Plumbaginaceae) and Diospyros species (Ebenaceae). comes. As such, both compounds are released from living (Juglans regia, Weiler Nover 2008) or, in any case, from degrading plant tissues and thereafter degraded microbially.
  • juglone Both substances, juglone and plumbagin are classified as pure substances as toxic (R phrases), but juglone has a high LD50 value (rat). This is contrasted with the presence of juglone in walnut as a crop for the diet. Especially when removing the exocarps of nuts, the human is exposed to the juglone strongly over the skin (recognizable as blackening of the fingers (oxidation, polymerization)). It is also used as a component of wool dyes and for the treatment of venous diseases. Furthermore, even alcoholic beverages based on immature walnuts are traditionally and commercially produced and consumed ("nut schnapps"). Subject to a required accurate assessment as a plant protection product according to the invention, therefore, juglone is initially considered to be rather harmless.
  • Exemplary representatives of three classes of quinones were compared in their effect on their effects on the growth of suspension cultures of Erwinia amylovora.
  • Fig. 4 shows the progressions of the growth curves in the presence of the various members of the classes as a function of the concentration (50/25/125/10/5/2.5 ⁇ M). It is clear (it should be noted the courses for 10 ⁇ M to 25 ⁇ M) that in this concentration range no representative of other quinone classes has an effect that is approximately comparable to the juglone. Only at the low concentration of 5 ⁇ M juglone does growth reappear after a long incubation period. 10 ⁇ M of juglone, corresponding to 1.74 mg / l, was still completely bactericidal.
  • Juglon has against Erwinia amylovora against other representatives tern of quinones, in each case described effect against various microorganisms, a beyond, special (bactericidal) effect.
  • the experiment was performed for growth inhibition curves with 0.1 or 0.01 mM juglone (20 ⁇ 10 mM and 1 mM juglone in ethanol to 2 ml of suspension cultures). 10 ⁇ aliquots of the cultures were taken immediately after addition of the juglone solution and mixing, as well as at regular time intervals and plated on juglone-free solid medium KB. As a control aliquots were taken from the suspension culture with an equivalent concentration of ethanol and also plated out. After two days incubation of the plates at 25 ° C, the respective colony formation was documented. Phytotoxizi did in flowers and for the subsequent fruit development
  • juglone and plumbagin were pre-dissolved in ethanol (65 ° C) and then diluted to the respective test concentrations in water. Maximum final concentration for the solvent ethanol in the treatment solutions was 5%, corresponding control treatments with 0.5 or 5% ethanol in water were performed. For each variant (active ingredient, concentration, variety) two larger branches were treated. The tests took place in the experimental fruit plant of the University of Natural Resources and Life Sciences in Jedlersdorf). All trees in a series were of the same age, developmental and observable physiological state. The treatments were in the morning from 8:00 to 9:30 at a rel.
  • Humidity of 68-75% and temperatures of 12-13 ° C performed. On all treatment days, the sprayed flowers were then exposed to direct sunlight. On the days following the treatment, phytotoxic effects were assessed. In the following months, fruit set and development were observed and compared with those of the control plants. Special attention was paid to visible changes in the fruit pidermis.
  • the in vitro infection tests with apple blossoms reflecting the natural route of infection were carried out as follows: Separated blooming apple blossoms were further cultured in sterile sugar solution standing in transparent plastic boxes. The stigmas of the flowers were inoculated with 10 4 cfu Erwinia amylovora cells and incubated for 2 hours at room temperature. Thereafter, the drug solutions to be tested were sprayed on. After a further 35 hours of incubation, it was moistened by spraying water. The infection rate was determined after 8-10 days of incubation at 22 ° C and 70% relative humidity.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Saccharide Compounds (AREA)

Abstract

La présente invention concerne l'utilisation d'un composé de formule (A) ou de formule (B), dans lesquelles R1, R4 et R5 représentent indépendamment H, un glucoside ou un ester, comme agent phytoprotecteur, l'agent phytoprotecteur renfermant ledit composé sous forme dissoute dans un solvant en concentration comprise entre 0,1 μM et 2 mM.
EP11705425A 2010-02-24 2011-02-24 Agent phytoprotecteur Withdrawn EP2538782A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ATA284/2010A AT509501B1 (de) 2010-02-24 2010-02-24 Pflanzenschutzmittel
PCT/AT2011/000092 WO2011103610A2 (fr) 2010-02-24 2011-02-24 Agent phytoprotecteur

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Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ587490A (en) * 2010-08-20 2013-03-28 Greentide Ltd Anti-Microbial Compounds containing compounds with a sugar substituent
CN104488977B (zh) * 2015-01-19 2017-09-05 湖北工程学院 枫杨树皮和果提取物及其新用途
CA2923767A1 (fr) * 2016-03-14 2017-09-14 Timothy R. St. Germain Methode d'utilisation de n-hydroxy-1,4-napthalenedione comme herbicide novateur
US11638425B2 (en) 2017-02-10 2023-05-02 National University Corporation Shizuoka University Agent for inducing stress tolerance in plants
CN108142445A (zh) * 2018-02-09 2018-06-12 湖北川玉茶业有限公司 一种植物农药和其制备方法及应用
CN110025624B (zh) * 2019-05-29 2021-04-02 济宁医学院附属医院 萘醌苷类化合物在老年痴呆中的应用及其药物制备
MX2022005652A (es) * 2019-11-15 2022-08-08 Vextachem S R L Agente fitosanitario y su uso particular en el tratamiento de plantas infectadas por xylella fastidiosa.
US12048309B2 (en) 2021-07-30 2024-07-30 University Of Wyoming Materials and methods for preventing and dispersing exopolysaccharide-containing biofilms involving Listeria monocytogenes
WO2024081610A1 (fr) * 2022-10-13 2024-04-18 Ag Nutrients, LLC Compositions, systèmes et procédés pour une qualité de plante accrue

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0134198A1 (fr) * 1983-08-10 1985-03-13 Ciba-Geigy Ag Utilisation des dérivés de quinone pour protéger les plantes cultivées contre l'effet phytotoxique des herbicides
GB2159056A (en) * 1984-04-04 1985-11-27 Alan Alaexander Torrance Sime Biocidal compositions comprising polyhydroxynaphthoquinones
US6164244A (en) 1998-03-20 2000-12-26 Pharmacognetics, Inc. Method for treating aquatic pests
AU5341699A (en) 1998-08-06 2000-02-28 University Of Pittsburgh Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof
GB9910787D0 (en) 1999-05-11 1999-07-07 Sorex Limited The treatment of pests using substituted naphthoquinones
JP4295402B2 (ja) 1999-10-01 2009-07-15 新日本石油株式会社 潤滑油組成物
US20060003894A1 (en) 2001-12-06 2006-01-05 Cutler Horace G Method of controlling zoological and aquatic plant growth
WO2006060582A2 (fr) * 2004-11-30 2006-06-08 Redox Chemicals, Inc. Nematicides de juglandacees et methodes pour les utiliser
CN1314327C (zh) * 2004-12-03 2007-05-09 武汉绿世纪生物工程有限责任公司 胡桃属植物提取物作为杀虫农药在防治小菜蛾上的应用
CN1836507A (zh) * 2006-04-22 2006-09-27 田官荣 一种防治红景天立枯病的药物
ATE444680T1 (de) 2006-05-02 2009-10-15 Nanosys Gmbh Verfahren zur bekämpfung von erwinia amylovora

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2011103610A2 *

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US20140343165A1 (en) 2014-11-20
WO2011103610A2 (fr) 2011-09-01
AT509501A1 (de) 2011-09-15
NZ602109A (en) 2014-05-30
CA2789808A1 (fr) 2011-09-01
AT509501B1 (de) 2012-06-15
US20120322889A1 (en) 2012-12-20

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