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Antifungale Formulierungen Enthaltend Einen Rheum

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Antifungale Formulierungen Enthaltend Einen Rheum (19) TZZ Z¥_T (11) EP 2 806 743 B1 (12) EUROPÄISCHE PATENTSCHRIFT (45) Veröffentlichungstag und Bekanntmachung des (51) Int Cl.: Hinweises auf die Patenterteilung: A01N 65/00 (2009.01) A01N 65/30 (2009.01) 06.09.2017 Patentblatt 2017/36 A01P 3/00 (2006.01) (21) Anmeldenummer: 13707264.1 (86) Internationale Anmeldenummer: PCT/DE2013/000031 (22) Anmeldetag: 17.01.2013 (87) Internationale Veröffentlichungsnummer: WO 2013/110258 (01.08.2013 Gazette 2013/31) (54) ANTIFUNGALE FORMULIERUNGEN ENTHALTEND EINEN RHEUM-WURZELEXTRAKT ZUR BEKÄMPFUNG VON PFLANZENKRANKHEITEN ANTIFUNGAL FORMULATIONS COMPRISING AN EXTRACT FROM RHEUM ROOTS FOR THE TREATMENT OF PLANT DISEASES FORMULATIONS ANTIFONGIQUES COMPRENANT UN EXTRAIT DES RACINES DE RHEUM POUR LE TRAITEMENT DES MALADIES DE PLANTES (84) Benannte Vertragsstaaten: (56) Entgegenhaltungen: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB EP-B1- 2 001 494 WO-A1-2007/112729 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO WO-A1-2007/112730 DE-A1- 4 411 895 PL PT RO RS SE SI SK SM TR • Volker Fischer: "Letter regarding (30) Priorität: 24.01.2012 DE 102012001867 EP07722138.0", , 22. Oktober 2008 (2008-10-22), Seiten 1-3, XP55062696, Gefunden im Internet: (43) Veröffentlichungstag der Anmeldung: URL:https://register.epo.org/espacenet/app 03.12.2014 Patentblatt 2014/49 lication?documentId=EN1M9U352612J13&appn um ber=EP07722138&showPdfPage=all (73) Patentinhaber: Hochschule Anhalt [gefunden am 2013-05-13] 06366 Köthen (DE) • Michelle Wilmot: "Inhibition of Phytopathogenic Fungion Selected Vegetable Crops by Catechins, (72) Erfinder: Caffeine, Theanine and Extracts of Camellia • BALTRUSCHAT, Helmut sinensis (L.) O. Kuntze", Master Thesis, Faculty 39619 Ziemendorf (DE) of Natural and Agricultural Sciences, University • KABROTH, Kathrin of Pretoria, 1. September 2006 (2006-09-01), 06406 Bernburg (DE) Seiten 1-132, XP55062694, Pretoria, South Africa • SCHELLENBERG, Ingo Gefunden im Internet: 06847 Dessau-Rosslau (DE) URL:http://upetd.up.ac.za/thesis/submitted /etd-07302008-144409/unrestricted/disserta (74) Vertreter: Fischer, Volker tion.pdf [gefunden am 2013-05-13] Sperling, Fischer & Heyner • DATABASE WPI Week 201071 Thomson Patentanwälte Scientific, London, GB; AN 2010-F92984 Bruno-Wille-Straße 9 XP002696903, & KR 2010 0048351 A (IGSBIO) 11. 39108 Magdeburg (DE) Mai 2010 (2010-05-11) Anmerkung: Innerhalb von neun Monaten nach Bekanntmachung des Hinweises auf die Erteilung des europäischen Patents im Europäischen Patentblatt kann jedermann nach Maßgabe der Ausführungsordnung beim Europäischen Patentamt gegen dieses Patent Einspruch einlegen. Der Einspruch gilt erst als eingelegt, wenn die Einspruchsgebühr entrichtet worden ist. (Art. 99(1) Europäisches Patentübereinkommen). EP 2 806 743 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 806 743 B1 Beschreibung [0001] Die Erfindung betrifft die Verwendung einer antifungalen Formulierung zur Bekämpfung von pilzlichen Pflan- zenkrankheiten, die zumindest Wirkstoffe oder Wirkstoffzusammensetzungen mit antifungaler Wirkung aus polypheno- 5 lischen Extrakten der Wurzeln von Rheum-Arten und anderen polyphenolhaltigen Pflanzen enthalten. [0002] Zahlreiche wichtige Kulturpflanzen sind häufig von Schädigungen betroffen, die auf pilzliche Erreger oder auf abiotischen Stress zurückgeführt werden können. Die pilzlichen Erreger werden zumeist mit synthetischen Fungiziden bekämpft, die ihrerseits allerdings zu nicht unerheblichen unerwünschten Nebenwirkungen führen können. [0003] Eine Alternative könnten Wirkstoffe oder Wirkstoffzusammensetzungen bieten, die auf pflanzlicher Basis ge- 10 wonnen werden. Der Einsatz rein pflanzlicher Wirkstoffe mit guter Wirkung gegen wichtige Pflanzenkrankheiten im Weinbau und in landwirtschaftlichen sowie gärtnerischen Kulturen kann die Möglichkeit der Produktion neuer innovativer Präparate schaffen. Zudem kann erwartet werden, dass die pflanzlichen Wirkstoffe einen neuartigen Wirkungsmecha- nismus gegen Pilzkrankheiten aufweisen. Wegen des hohen Risikos der Resistenzbildung von pilzlichen Krankheiten gegenüber synthetischen fungiziden Wirkstoffen und auch aufgrund der Tatsache, dass viele der eingesetzten fungiziden 15 Wirkstoffe den gleichen Wirkungsmechanismus gegenüber bestimmten Pflanzenkrankheiten haben, werden in der Pra- xis dringend Präparate mit einem neuartigen Wirkungsmechanismus benötigt. [0004] Aus der DE-PS 484 489 ist ein Verfahren zur Bekämpfung von Pflanzenschädlingen bekannt. Darin wird die Wirksamkeit pflanzlicher Extrakte zur Bekämpfung von Schädlingen bei Obstgehölzen durch Einführung in den Saftstrom beschrieben. Rhabarber erscheint dabei in der Aufzählung der nutzbaren Pflanzen. 20 [0005] Die DE 4411 895 A1 beschreibt ein Verfahren zur Bekämpfung von Pilzen auf Pflanzen, Materialien und Saatgut durch das Einwirken einer fungizid wirksamen Menge von Rheum rhabarbarum und Solidago canadensis. Beispielsweise werden Plasmopara viticola als Erreger bei Wein, Phytophthora infestans als Erreger von Krautfäule bei Kartoffeln, Erysiphe cichoracearum als Erreger des Gurkenmehltaus und Botrytis cinerea als Erreger bei Paprika aufgeführt. [0006] In der US 2011/0053771 A1 wird die Verwendung von Gerbstoffen zur Stärkung der Pflanzen gegen die Infektion 25 durch pilzliche Erreger, zum Beispiel Blumeria graminis, beschrieben. [0007] In der Dissertationsschrift von Michelle Wilmot mit dem Titel "Inhibition of Phytopathogenic Fungi on Selected Vegetable Crops by Catechins, Caffeine, Theanine and Extracts of Camellia sinensis (L.) O. Kuntze", Master Thesis, Faculty of Natural and Agricultural Sciences, University of Pretoria, 1. September 2006, Seiten 1 bis 132, ist offenbart, dass Epicatechin, Epigallocatechin und Epigallocatechingallat gegen eine große Zahl an pflanzen pathogenen Pilzen 30 inhibierend wirken. Insbesondere sind die Ergebnisse einer in vitro Inhibition des Pilzwachstums durch Epicatechin (EC), Epigallocatechin (EGC), Epicatechingallat (Ecg) bei einer Konzentration von 2,5 g*L -1 aufgeführt. [0008] Aus der KR 2010 0048351 A ist ein Extrakt aus Rheum undulatum zur Kontrolle von durch Pilze verursachten Pflanzenerkrankungen bekannt. [0009] Wie bei den oben beschriebenen Anwendungen werden bisher im Allgemeinen überwiegend die oberirdischen 35 Teile der Pflanzen verwendet. Des Weiteren wurden für die meisten Anwendungen lediglich protektive Effekte beschrie- ben. [0010] Die Aufgabe der Erfindung besteht in der Bereitstellung von Formulierungen mit einem oder mehreren Wirk- stoffen auf pflanzlicher Basis für eine Verwendung zur Bekämpfung von pilzlichen Pflanzenkrankheiten. Solche Formu- lierungen sollten dabei idealerweise sowohl protektiv als auch kurativ wirksam sein. 40 [0011] Die Lösung dieser Aufgabe der Erfindung liegt in der Verwendung einer antifungalen Formulierung zur Be- kämpfung von pilzlichen Pflanzenkrankheiten, wobei zu den zu bekämpfenden phytopathogenen Pilzen ein oder mehrere phytopathogene Pilze gehören und die antifungale Formulierung zumindest Wirkstoffe oder Wirkstoffzusammensetzun- gen mit antifungaler Wirkung aus polyphenolischen, keine Anthrachinone und Anthrachinonderivate enthaltenden Ex- trakten der Wurzeln von Rheum-Arten enthält, wobei diese Wirkstoffe oder Wirkstoffzusammensetzungen erhältlich sind 45 durch ein Verfahren, umfassend die folgenden Verfahrensschritte: a) kontinuierlich oder batchweise durchgeführte ein- oder mehrstufige Extraktion der gereinigten und zerkleinerten Wurzeln, wobei die Wurzeln ungetrocknet oder getrocknet, vorzugsweise getrocknet und gemahlen, eingesetzt werden mittels eines alkoholischen Lösungsmittels; 50 b) schonende Entfernung des alkoholischen Lösungsmittels bei reduziertem Druck und bei Temperaturen bis ma- ximal 50 °C unter Zugabe von Wasser, wobei • aus der gebildeten wässrigen Phase lipophile Begleitstoffe durch Kühlen bei einer Temperatur von 2 bis 8 °C ausgefällt und mittels Filtration oder Zentrifugation entfernt werden und weitere lipophile Begleitstoffe durch 55 anschließendes Ausschütteln der wässrigen Phase mit Petrolether entfernt werden oder • aus der gebildeten wässrigen Phase lipophile Begleitstoffe mittels flüssig/flüssig-chromatografischer Verfahren abgetrennt werden; 2 EP 2 806 743 B1 c) extraktive Auftrennung des unter b) gewonnenen wässrigen Extraktes unter Verwendung eines organischen Lösungsmittels aus der Gruppe der Ester, wie zum Beispiel Essigsäureethylester, in eine hydrophile und eine hydrophobe Phase; und d) Gewinnung von Extrakten aus beiden Extraktphasen des Verfahrensschrittes c). 5 [0012] Gemäß der Erfindung werden polyphenolische Extrakte, die in der oben beschriebenen Weise erhältlich sind, im Verfahrensschritt d) mit den Teilschritten d1) bis d3) gewonnen, bei denen d1) eine säulenchromatografische Auftrennung an Sephadex LH-20 der hydrophoben Extraktphase oder der hy- 10 drophilen Extraktphase erfolgt, wobei als Elutionsmittel nacheinander unterschiedliche Alkohole, bevorzugt Metha- nol, Ethanol, Propanol oder Butanol, und ein Gemisch aus Lösungsmitteln der Alkanone-Reihe, vorzugsweise Pro- panon, Butanon oder Pentanon, und Wasser eingesetzt werden, wonach eine begrenzte Anzahl von Fraktionen resultiert und danach d2) die gewonnenen Fraktionen aus der hydrophoben Phase oder der hydrophilen Phase mit jeweils gleichem 15 Inhaltsstoffspektrum zu Wirkstofffraktionen zusammengefasst werden können, worauf d3) eine Auswahl einzelner Wirkstofffraktionen zur Verwendung nach Durchführung eines Wirksamkeitsnachweises der Wirkstofffraktionen hinsichtlich ihrer protektiven und/oder kurativen Wirksamkeit gegenüber phytopathogenen Pilzen getroffen
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