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Paraffinic Oil-In-Water Emulsions for Controlling Infection of Crop Plants by Fungal Pathogens

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Paraffinic Oil-In-Water Emulsions for Controlling Infection of Crop Plants by Fungal Pathogens (19) TZZ _¥_T (11) EP 2 713 749 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 27/00 (2006.01) A01N 25/04 (2006.01) 22.05.2019 Bulletin 2019/21 A01N 37/50 (2006.01) A01N 43/54 (2006.01) A01N 43/653 (2006.01) A01N 47/24 (2006.01) (2006.01) (2006.01) (21) Application number: 12793919.7 A01P 3/00 A01N 43/40 A01N 43/50 (2006.01) A01N 43/60 (2006.01) A01N 43/76 (2006.01) A01N 43/88 (2006.01) (22) Date of filing: 04.06.2012 A01N 47/14 (2006.01) A01N 47/38 (2006.01) A01N 55/00 (2006.01) (86) International application number: PCT/CA2012/050376 (87) International publication number: WO 2012/162846 (06.12.2012 Gazette 2012/49) (54) PARAFFINIC OIL-IN-WATER EMULSIONS FOR CONTROLLING INFECTION OF CROP PLANTS BY FUNGAL PATHOGENS PARAFFINISCHE ÖL-IN-WASSER-EMULSIONEN ZUR STEUERUNG DER INFEKTION VON ZUCHTPFLANZEN DURCH PATHOGENE PILZE ÉMULSIONS HUILE PARAFFINIQUE DANS EAU UTILISABLES EN VUE DE LA LUTTE CONTRE LES INFECTIONS PAR DES CHAMPIGNONS PATHOGÈNES CHEZ LES PLANTES CULTIVÉES (84) Designated Contracting States: (56) References cited: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB EP-A2- 0 267 778 WO-A1-2009/155693 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO WO-A1-2009/155693 WO-A2-2012/040804 PL PT RO RS SE SI SK SM TR CA-A1- 2 507 482 US-A- 4 041 164 US-A- 5 393 770 (30) Priority: 03.06.2011 US 201161493118 P 13.06.2011 US 201161496500 P • G C Schutte ET AL: "Application of azoxystrobin for control of benomyl-resistant Guignardia (43) Date of publication of application: citricarpa on ’Valencia’ oranges in South Africa", 09.04.2014 Bulletin 2014/15 Plant Disease, 1 July 2003 (2003-07-01), page 784, XP055138019, St. Paul Retrieved from the (73) Proprietor: Suncor Energy Inc. Internet: Calgary, Alberta T2P 3E3 (CA) URL:http://search.proquest.com/docview/229 879498 [retrieved on 2014-09-29] (72) Inventors: • Janna Beckerman: "Disease Management • FEFER, Michael Strategies for Horticultural Crops Using organic Whitby, Ontario L1N 7A7 (CA) Fungicides", Purdue Extension, 1 April 2008 •LIU,Jun (2008-04-01), pages 1-4, XP055143138, Retrieved Oakville, Ontario L6H 6H3 (CA) from the Internet: URL:https://www.extension.purdue.edu/extme (74) Representative: Peterreins Schley dia/bp/bp-69-w.pdf [retrieved on 2014-09-29] Patent- und Rechtsanwälte Hermann-Sack-Strasse 3 80331 München (DE) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 713 749 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 713 749 B1 • "SUNSPRAY 6E - Material Safety Data Sheet", , 1 • SCHUTTE, G.C. ET AL.: ’Application of June 2009 (2009-06-01), pages 1-5, XP055143573, azoxystrobin for control of benomyl-resistant Retrieved from the Internet: Guignardia citricarpa on ’Valencia’ oranges in URL:http://www.recarroll.com/cw3/Assets/pr South Africa’ PLANT DISEASE vol. 87, no. 7, 01 oduct_files/Sunspray 6E.pdf [retrieved on July 2003, pages 784 - 788, XP055138019 2014-09-30] • SOOMARY, S.D. ET AL.: ’Evaluation of Remarks: Fungicides for Control of the Leaf Spot Disease Thefile contains technical information submitted after Caused by Mycosphaerella eumusae on Banana the application was filed and not included in this in Mauritius’ FOOD AND AGRICULTURAL specification RESEARCH COUNCIL, PROCEEDINGS FOURTH ANNUAL MEETING OF AGRICULTURAL SCIENTISTS February 2001, pages 61 - 65, XP008171895 • DELL, K.J. ET AL.: ’The efficacy of JMS Sylet-Oil on grape powdery mildew and Botrytis bunch rot and effects on fermentation’ AMERICAN JOURNAL OF ENOLOY AND VITICULTURE vol. 49, no. 1, 1998, pages 11 - 16, XP055138346 2 EP 2 713 749 B1 Description TECHNICAL FIELD 5 [0001] The present invention relates to the use of a fungicidal composition comprising: a paraffinic oil, an emulsifier, a copper phthalocyanine pigment and a silicone surfactant and wherein:the ratio of the paraffinic oil to the pigment is from about 5:1 to 100:1; the weight ratio of the paraffinic oil to the emulsifier is from 10:1 to 500:1; and the weight ratio of the pigment to the silicone surfactant is from 2:1 to 50:1, for controlling infection of a crop plant by a fungal pathogens. Also disclosed are combinations containing a paraffinic oil and one or more of the following: one or more emulsifiers, 10 one or more pigments, one or more silicone surfactants, one or more anti-settling agents, one or more conventional chemical fungicides (e.g., a DMI or a QoI), and water. In some implementations, the combinations can be in the form of a single composition (e.g., which is contained within a storage pack or a vessel (e.g., a tank) suitable for applying the composition to a plant, e.g., crop plant). Typically, the composition is applied to a plant after dilution with water. In other implementations, the combinations can include two or more separately contained (e.g., packaged) compositions, each 15 containing one or more of the above-mentioned components. Said compositions can be combined and applied to a plant typically after dilution with water; or each composition can be applied separately to the same plant either simultaneously or sequentially, and typically after dilution with water. This disclosure also features methods of using the combinations for controlling infection of a vascular crop plant by a fungal pathogen as well as methods of formulating combinations that include both oil and water as oil-in-water (O/W) emulsions. 20 BACKGROUND [0002] Rusts are plant diseases caused by fungal pathogens of the order Pucciniales. Rusts can affect a variety of plants, including monocotyledons and dicotyledons, as well as various plant organs, including leaves, stems, fruits and 25 seeds. Rust is typically observed as colored powdery pustules composed off tiny spores that form on the lower plant organ surfaces. Common rust-causing fungal species include Gymnosporangium juniperi-virginianae (Cedar-apple rust) which attacks apple and pear and hawthorn; Cronartium ribicola (White pine blister rust); which attacks white pines and currants; Hemileia vastatrix (Coffee rust) which attacks coffee plant; Puccinia graminis (wheat stem rust) which attacks Kentucky bluegrass, barley, and wheat; Puccinia coronata (Crown Rust of Oats and Ryegrass) which attacks oats; 30 Phakopsora meibomiae and P. pachyrhizi (soybean rust) which attacks soybean and various legumes; Uromyces pha- seoli (Bean rust) which attacks bean; Puccinia hemerocallidis (Daylily rust) which attacks Daylily; Puccinia persistens subsp. triticina causes (wheat rust in grains, also known as ’brown or red rust’); P. sriiformis (yellow or stripe rust); Uromyces appendeculatus which attacks bean. [0003] Wheat stem rust is caused by the fungus Puccinia graminis and is a significant disease affecting cereal crops, 35 particularly wheat (Triticum spp.) An epidemic of stem rust on wheat caused by race Ug99 is currently spreading across Africa, the Middle East, and Asia, and threatening large numbers of people who are dependent on wheat for sustenance. The rust fungus attacks the parts of the plant which are above ground. Spores that land on green wheat plants form a pustule that invades the outer layers of the stalk. Where infection has occurred on the stem or leaf, elliptical blisters or pustules called uredia develop. Infected plants produce fewer tillers and set fewer seed. 40 [0004] Soybean rust is a disease that primarily affects soybeans and other legumes. It is caused by two species of fungi, Phakopsora pachyrhizi and Phakopsora meibomiae. Soybean rust has been reported in Asia, Australia, Africa, South America and North America. Soybean rust is spread by wind-borne spores, which are released in cycles of seven days to two weeks. Yield losses can be severe with this disease and losses of 10-80% have been reported. [0005] Multi-pronged approaches are desirable to address the spread of fungal infection. A variety of preventative 45 methods may be employed. For example, rust diseases are correlated to relatively high moisture. Accordingly, avoidance of overhead watering at night, using drip irrigation, reducing crop density, and the use of fans to circulate air flow may serve to lower the relative moisture and decrease the severity of rust infection. [0006] Other strategies may include reducing the area of the plant that the pathogen destroys, or slowing down the spread of the fungus. Fungus-resistant plants may be used to interrupt the disease cycle because many rusts are host- 50 specific. This approach has proven very successful in the past for control of wheat stem rust; however, Ug99 is currently virulent against most wheat varieties. Currently, there are no commercial soybean varieties with resistance to soybean rust. Accordingly, soybean rust is managed with fungicides. [0007] In large agricultural operations, conventional synthetic fungicides can be used to control fungal pathogens. De- methylation inibitors (DMI) such tebuconazole (Folicur™, Bayer) and propioconazole (Tilt™) may be effective for the 55 control of wheat stem rust, while tetraconazole (Domark™, Valent) be effective for the control of soybean rust. Quinone Outside Inhibitors (QoI), such as pyraclostrobin (Headline™, BASF), may be effective for the control of soybean rust, while azoxystrobin (Quadris™) may be effective for the control of wheat stem rust. [0008] Conventional fungicides are generally applied by air to the foliage as contact between the pathogen with the 3 EP 2 713 749 B1 fungicide is required for efficacy.
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