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Synergistic Herbicidal Composition Containing (19) TZZ ¥¥___T (11) EP 2 493 311 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 43/54 (2006.01) A01N 43/40 (2006.01) 13.07.2016 Bulletin 2016/28 A01P 13/02 (2006.01) A01N 25/32 (2006.01) (21) Application number: 10773505.2 (86) International application number: PCT/US2010/054221 (22) Date of filing: 27.10.2010 (87) International publication number: WO 2011/056631 (12.05.2011 Gazette 2011/19) (54) SYNERGISTIC HERBICIDAL COMPOSITION CONTAINING FLUROXYPYR AND PENOXSULAM SYNERGISTISCHE HERBIZIDZUSAMMENSETZUNG MIT FLUROXYPYR UND PENOXSULAM COMPOSITION HERBICIDE SYNERGIQUE CONTENANT DU FLUROXYPYR ET DU PENOXSULAME (84) Designated Contracting States: (74) Representative: f & e patent AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Fleischer, Engels & Partner mbB, Patentanwälte GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Braunsberger Feld 29 PL PT RO RS SE SI SK SM TR 51429 Bergisch Gladbach (DE) Designated Extension States: BA ME (56) References cited: EP-A1- 0 512 739 WO-A2-2008/058622 (30) Priority: 28.10.2009 US 255689 P WO-A2-2009/152827 AU-B2- 606 560 US-A- 5 990 047 (43) Date of publication of application: 05.09.2012 Bulletin 2012/36 • DATABASE WPI Section Ch, Week 200969 Thomson Scientific, London, GB; Class A97, AN (60) Divisional application: 2009-N99318 XP002651295, "Herbicide 16152976.3 / 3 036 993 composition for preventing graminaceous and broadleaved weed in rice field comprises active (73) Proprietor: Dow AgroSciences LLC ingredients including sulfonylurea or its salt, Indianapolis, IN 46268 (US) pyridines and penoxsulam at specified weight ratio", -& CN 101 530 105 A (BEIJING (72) Inventors: YINGTAIJIAHE SCIENCE) 16 September 2009 • MANN, Richard (2009-09-16) Franklin • DATABASE WPI Section Ch, Week 200828 IN 46131 (US) Thomson Scientific, London, GB; Class C02, AN • WEIMER, Monte 2008-D85552 XP002651296, "Herbicide Pittsboro composition for controlling grassy weeds and IN 46167 (US) broadleaf weed in corn field, comprises • MCVEIGH-NELSON, Ändrea nicosulfuron, fluroxypyr, dispersant agent, Indianapolis wetting agent and light calcium", -& CN 101 066 IN 46260 (US) 056 A (ZHAO BANGBIN CHEN [CN]) 7 November •ELLIS,Andrew 2007 (2007-11-07) Greenville MS 38701 (US) 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 2 493 311 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 493 311 B1 • DATABASE WPI Section Ch, Week 200974 • Kristie J. Pellerin: "MANAGEMENT OF Thomson Scientific, London, GB; Class A97, AN IMIDAZOLINONE TOLERANT (IT) RICE IN DRILL- 2009-N99319 XP002645687, "Herbicide ANDWATERSEEDED RICE", Thesis Submitted to composition for treating annual perennial the Graduate Faculty of the Louisiana State graminaceous and broadleaved weed of rice field University and Agricultural and Mechanical comprises sulfonylurea, pyridines and College in partial fulfillment of the requirements cyhalofop-butyl at specified weight ratio", -& CN for the degree of Master of Science in The 101 530 104 A (BEIJING YINGTAI JIAHE Department of Plant Pathology and Crop TECHNOLOGY CO LTD) 16 September 2009 Physiology, 1 December 2002 (2002-12-01), (2009-09-16) XP055022983, Retrieved from the Internet: • DAVID W. BROWN ET AL: "Safening grain URL:http://etd.lsu.edu/docs/available/etd- sorghum injury from metsulfuron with growth 1113102-140006/unrestricted/Pellerin_thesi regulator herbicides", WEED SCIENCE, vol. 52, 1 s.pdf [retrieved on 2012-03-26] January 2004 (2004-01-01), pages 319-325, • Anonymous: "Clearmax herbicide Label", BASF XP055001834, DOI: 10.1614/P2002-074 Corporation , 1 January 2008 (2008-01-01), • DATABASE WPI Section Ch, Week 200967 XP055022990, Retrieved from the Internet: Thomson Scientific, London, GB; Class C02, AN URL:http://fs1.agrian.com/pdfs/Clearmax_He 2009-P07796 XP002672428, "Herbicide rbicide_Label1.pdf [retrieved on 2012-03-26] composition for preventing gramineous weeds • MONTE R. WEIMER ET AL: "PERFORMANCE OF and broad-leaved weeds comprises CEREAL GRASS HERBICIDES IN TANK-MIX nicosulfuron,atrazine and fluroxypyr at specified COMBINATIONS WITH FLUROXYPYR, weight ratio", -& CN 101 530 103 A (SHANXI CLOPYRALID, AMINOPYRALID, BROMOXYNIL, SUNGER ROAD BIO SCIENCE) 16 September AND MCPA MIXTURES.", NORTH CENTRAL 2009 (2009-09-16) WEED SCIENCE SOCIETY PROCEEDINGS, vol. • DATABASE WPI Section Ch, Week 200943 61, 1 January 2006 (2006-01-01), page 105, Thomson Scientific, London, GB; Class C02, AN XP055022996, 2009-J82999 XP002672429, -& CN 101 433 205 A • Rodney G Lym ET AL: "Leafy spurge control with (SINOCHEM CORP [CN] SINOCHEM CORP various picolinic acid herbicides", Leafy Spurge SHENYANG RES I O [CN]) 20 May 2009 Symposium. Riverton, WY., 9 July 1986 (2009-05-20) (1986-07-09), pages 78-79, XP055022790, • PELLERIN KRISTIE J ET AL: "Potential use of Retrieved from the Internet: imazethapyr mixtures in drill-seeded URL:http://library.ndsu.edu/tools/dspace/l imidazolinone-resistant rice", WEED oad/?file=/repository/bitstream/handle/103 TECHNOLOGY, vol. 18, no. 4, 1 October 2004 65/3822/1575LY86.PDF?sequence=1 [retrieved (2004-10-01), pages 1037-1042, XP002605743, on 2012-03-23] CHAMPAIGN, IL, US ISSN: 0890-037X, DOI: • DATABASE WPI Section Ch, Week 201029 10.1614/WT-03-214 Thomson Scientific, London, GB; Class C02, AN • LARRY R NELSON ET AL: "Imazapyr and 2010-D58704 XP002672430, -& CN 101 669 482 A Triclopyr Tank Mixtures for Basal Bark Control of (HEFEI XINGYU CHEMICAL CO LTD) 17 March Woody Brushin the Southeastern United States", 2010 (2010-03-17) NEW FORESTS, vol. 31, no. 2, 1 March 2006 (2006-03-01), pages 173-183, XP019260382, KLUWER ACADEMIC PUBLISHERS, DO ISSN: 1573-5095 • Mathew C. Nespeca: "Interactive Effects of Imazapyr plus Triclopyr ester and Imazapyr plus Glyphosate Mixtures on Woody Weed Seedlings - abstract", Thesis submitted to the Faculty of the Virginia Polytechnic Institute and State University in partial fulfillment of the requirements for the degree of Master of Science in Forestry, 17 October 1997 (1997-10-17), XP055022988, Blacksburg, VA Retrieved from the Internet: URL:http://scholar.lib.vt.edu/theses/avail able/etd-93197-152836/unrestricted/abst.PD F [retrieved on 2012-03-26] 2 EP 2 493 311 B1 Description [0001] This invention concerns a synergistic herbicidal composition consisting of (a) fluroxypyr and (b) penoxsulam for controlling weeds in crops, especially rice, cereal and grain crops, pastures, rangelands, industrial vegetation man- 5 agement (IVM) and turf. These compositions provide improved post-emergence herbicidal weed control. [0002] The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. 10 [0003] CN 101 530 105 A relates to herbicidal compositions containing ternary mixtures of a sulfonylurea herbicide or a salt thereof, a pyridine herbicide and penoxsulam. However, no synergism is reported for the respective mixtures. [0004] In some cases, herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as "synergism." As described in the Herbicide Handbook of the Weed Science Society of America, Eighth Edition, 2002, p. 462 "’synergism’ [is] an interaction of two or more factors such that the effect 15 when combined is greater than the predicted effect based on the response to each factor applied separately." The present invention is based on the discovery that fluroxypyr, penoxsulam, halosulfuron-methyl and imazamox, already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination. [0005] The herbicidal compounds forming the synergistic composition of this invention are independently known in the art for their effects on plant growth. 20 [0006] The present invention concerns a synergistic herbicidal mixture consisting of an herbicidally effective amount of (a) fluroxypyr and (b) the acetolactate synthase (ALS) inhibitor herbicide penoxsulam. The compositions may also contain an agriculturally acceptable adjuvant and/or carrier. [0007] The present invention also concerns herbicidal compositions for and methods of controlling the growth of undesirable vegetation, particularly in monocot crops including rice, wheat, barley, oats, rye, sorghum, corn, maize, 25 pastures, grasslands, rangelands, fallowland, turf, IVM and aquatics and the use of these synergistic compositions. [0008] The species spectra of the ALS inhibitor penoxsulam, i.e., the weed species which the respective compound controls, are broad and highly complementary with that of fluroxypyr. For example, it has been surprisingly found that a combination of penoxsulam and fluroxypyr exhibits a synergistic action in the control of Hemp sesbaniaSesbania ( exaltata; SEBEX), Texasweed (Caperonia palustris; CNPPA), Japanese bulrush (Scirpus juncoides; SCPJU), narrow- 30 leaved plantain
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