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(12) United States Patent (10) Patent No.: US 9,089,135 B2 Andersch Et Al

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(12) United States Patent (10) Patent No.: US 9,089,135 B2 Andersch Et Al US009089135B2 (12) United States Patent (10) Patent No.: US 9,089,135 B2 Andersch et al. (45) Date of Patent: Jul. 28, 2015 (54) NEMATICIDAL, INSECTICIDAL AND 2003/0176428 A1 9/2003 Schneidersmann et al. ACARCIDAL ACTIVE INGREDIENT 2006/01 11403 A1 5/2006 Hughes et al. 2007/02O3191, A1* 8/2007 Loso et al. .................... 514,336 COMBINATIONS COMPRISING 2009, O247551 A1 10/2009 Jeschke et al. PYRIDYL-ETHYLBENZAMIDES AND 2009,0253749 A1 10/2009 Jeschke et al. INSECTICDES 2010/024O705 A1 9/2010 Jeschke et al. 2011 0110906 A1 5/2011 Andersch et al. (75) Inventors: Wolfram Andersch, Bergisch Gladbach 2014,0005047 A1 1/2014 Hungenberg elal. (DE); Heike Hungenberg, Langenfeld FOREIGN PATENT DOCUMENTS (DE); Heiko Rieck, Burscheid (DE) EP O 146748 B1 5, 1988 (73) Assignee: Bayer Intellectual Property GmbH, EP O 16O 344 B1 6, 1988 EP O538588 A1 4f1993 Monheim (DE) EP O 580374, A1 1, 1994 WO WO 83,0087.0 A1 3, 1983 (*) Notice: Subject to any disclaimer, the term of this WO WO 97.22593 A1 6, 1997 patent is extended or adjusted under 35 WO WO 02/28.186 A2 4/2002 U.S.C. 154(b) by 361 days. WO WO O2/080675 A1 10, 2002 WO WOO3,O15519 A1 2, 2003 WO WO 2004/O16088 A2 2, 2004 (21) Appl. No.: 12/731,812 WO WO 2005, O77901 A1 8, 2005 WO WO 2007 115646 A1 10/2007 (22) Filed: Mar. 25, 2010 WO WO 2007 115644 A1 * 10, 2007 WO WO 2007/149134 A1 12/2007 (65) Prior Publication Data WO WO 2008/OO3738 A1 1, 2008 WO WO 20091472O5 A2 * 12/2009 US 2010/O249.193 A1 Sep. 30, 2010 OTHER PUBLICATIONS (30) Foreign Application Priority Data Bauer, T.A., et al., “Response of Selected Weed Species to Postemergence Imazethapyr and Bentazon.” Weed Tech. 9:236-242, Mar. 25, 2009 (EP) ..................................... 0.9156175 The Weed Science Society of America, United States (1995). Blackshaw, R.E., "HOE-39866 Use in Chemical Fallow Systems.” (51) Int. Cl. Weed Tech. 3:420-428. The Weed Science Society of America, United AOIN 25/00 (2006.01) States (1989). AOIN 43/40 (2006.01) Blackshaw, R.E., "Synergistic Mixes of DPX-A7881 and Clopyralid (52) U.S. Cl. in Canola (Brassica napus).' Weed Tech. 3:690-695. The Weed Sci CPC ...................................... A0IN 43/40 (2013.01) ence Society of America, United States (1989). (58) Field of Classification Search Blackshaw, R.E., et al., “Herbicide Combinations for Postemergent CPC ......................................................... CO5G 3/02 Weed Control in Safflower (Carthamus tinctorius).' Weed Tech. 4: 97 104. The Weed Science Society of America, United States (1990). USPC .......................................................... 424/405 Blouin, D.C., et al., “Analysis of Synergistic and Antagonistic Effects See application file for complete search history. of Herbicides Using Nonlinear Mixed-Model Methodology.” Weed Tech. 18:464–472. The Weed Science Society of America, United (56) References Cited States (2004). Bradley, P.R., et al., “Response of Sorghum (Sorghum bicolor) to U.S. PATENT DOCUMENTS Atrazine, Ammonium Sulfate, and Glyphosate.” Weed Tech. 14:15 2,596,076 A 5, 1952 Hook et al. 18. The Weed Science Society of America, United States (2000). 2.978.479 A 4, 1961 Kayser et al. Buker, III, R.S., et al., “Confirmation and Control of a Paraquat 3,112,244. A 1 1/1963 Goyette et al. Tolerant Goosegrass (Eleusine indica) Biotype.” Weed Tech. 16:309 3,217,037 A 1 1/1965 Payne, Jr. et al. 313. The Weed Science Society of America, United States (2002). 3.244,586 A 4/1966 Rigterink Burke, I.C., et al., “CGA-362622 Antagonizes Annual Grass Control 3,313,684. A 4/1967 Schegk et al. with Clethodim.” Weed Tech. 16:749-754, The Weed Science Society 3,470,299 A 9, 1969 Heiss et al. of America, United States (2002). 3,530,220 A 9, 1970 Buchanan et al. 3,867,396 A 2f1975 Dawes et al. (Continued) 3,962,316 A 6, 1976 Kiehset al. 4,004,031 A 1/1977 Drabek et al. Primary Examiner — Benjamin Packard 4,006,231 A 2f1977 Black et al. 4,245,432 A 1/1981 Dannelly et al. (74) Attorney, Agent, or Firm — Sterne, Kessler, Goldstein 4,272.417 A 6, 1981 Barke et al. & FOX PLLC 4,310,519 A 1/1982 Albers-Schonberg et al. 4,474,775 A 10, 1984 Okada et al. (57) ABSTRACT 4,782,174 A 11, 1988 Fuchs et al. 4,808.430 A 2f1989 Kouno The present invention relates to novel active ingredient com 4,889,872 A 12, 1989 Naumann et al. binations which consist of fluopyram and further known 5,876.739 A 3, 1999 Turnbladet al. active insecticidal ingredients, and are very Suitable for con 6,114,374. A 9, 2000 Lieb et al. 6.255,342 B1 7/2001 Lieb et al. trolling animal pests, such as insects and/or unwanted acarids 6,359,151 B2 3, 2002 Lieb et al. and/or nematodes, in foliar and soil application and/or in seed 7,247,647 B2 7/2007 Hughes et al. treatment. 7,572,818 B2 8, 2009 Mansfield et al. 2002/0010204 A1 1/2002 Lieb et al. 28 Claims, No Drawings US 9,089,135 B2 Page 2 (56) References Cited Palmer, E.W., et al., “Broadleaf Weed Control in Soybean (Glycine max) with CGA-277476 and Four Postemergence Herbicides.” Weed OTHER PUBLICATIONS Tech. 14:617-623. The Weed Science Society of America, United States (2000). Colby, S.R., "Calculating synergistic and antagonistic responses of Rummens, F.H.A., “An Improved Definition of Synergistic and herbicide Combinations.” Weeds 15:20-22, Weed Science Society of Antagonistic Effects.” Weed Science 23(1):4-6, The Weed Science America, United States (1967). Society of America, United States (1975). Flint, J.L., et al., “Analyzing Herbicide Interactions, a Statistical Salzman, F.P., and Renner, K.A., “Response of Soybean to Combi Treatment of Colby's Method.” Weed Tech. 2:304-309. The Weed nations of ClomaZone, Metribuzin, Linuron, Alachlor, and Atrazine.” Science Society of America, United States (1988). Weed Tech. 6:922-929. The Weed Science Society of America, United Gillespie, G.R., and Nalewaja, J.D., “Wheat (Triticum aestivum) States (1992). Scott, R.C., et al., “Spray Adjuvant, Formulation, and Environmental Response to Triallate Plus Chlorsulfuron.” Weed Tech. 3:20-23. The Effects on Synergism from Post-Applied Tank Mixtures of SAN Weed Science Society of America, United States (1989). 582H with Fluazifop-P Imazethapyr, and Sethoxydim.” Weed Tech. Green, J.M., et al., “Metribuzin and Chlorimuron Mixtures for 12:463-469. The Weed Science Society of America, United States Preemergence Broadleaf Weed Control in Soybeans, Glycine may," (1998). Weed Tech. 2:355-363, The Weed Science Society of America, United Shaw, D.R. and Arnold, J.C., "Weed Control from Herbicide Com States (1988). binations with Glyphosate.” Weed Tech. 16:1-6. The Weed Science Harker, N.K., and O'Sullivan, P.A., “Synergistic Mixtures of Society of America, United States (2002). Sethoxydim and Fluazifop on Annual Grass Weeds.” Weed Tech. Snipes, C.E., and Allen, R.L., “Interaction of Graminicides Applied 5:310-316, The Weed Science Society of America, United States in Combination with Pyrithiobac.” Weed Tech. 10:889-892, The (1991). Weed Science Society of America, United States (1996). Kent, L.M., et al., “Effect of Ammonium Sulfate, Imazapyr, and Sun, Y.-P. & Johnson, E.R., “Analysis of Joint Action of Insecticides Environment on the Phytotoxicity of Imazethapyr.” Weed Tech. against House Flies'. J. Econ. Entomol., 53:887-892, Journal of 5:202-205, The Weed Science Society of America, United States Economic Entomology, United States (1960). (1991). Wehtje, G. and Walker, R.H., “Interaction of Glyphosate and 2,4-DB Kotoula-Syka, E., et al., “Interactions between SAN 582H and for the Control of Selected Morningglory (Ipomoea spp.) Species.” Selected Safeners on Grain Sorghum (Sorghum bicolor) and Corn Weed Tech. 11:152-156. The Weed Science Society of America, (Zea mays).” Weed Tech. 10:299-304, The Weed Science Society of United States (1997). America, United States (1996). Zhang, W., et al., “Fenoxaprop Interactions for Barnyardgrass Lanclos, D.Y., et al., "Glufosinate Tank-Mix Combinations in (Echinochloa crus-galli) Control in Rice.” Weed Tech. 19:293-297. Glufosinate-Resistant Rice (Oryza sativa).' Weed Tech. 16:659-663, The Weed Science Society of America, United States (2005). The Weed Science Society of America, United States (2002). English language abstract of European Patent Publication No. EPO Norris, J.L., et al., "Weed Control from Herbicide Combinations with 538588 A1 (1993). Three Formulations of Glyphosate.” Weed Tech. 15:552-558. The Office Action mailed Dec. 8, 2014, in U.S. Appl. No. 13/990,586, Weed Science Society of America, United States (2001). Hungenberg, H., et al., S371 (c) Date: Sep. 18, 2013, U.S. Patent and Novosel, K.M., et al., “Metolachlor Efficacy as Influenced by Three Trademark Office, Alexandria, VA. Acetolactate Synthase-Inhibiting Herbicides.” Weed Tech. 12:248 253, The Weed Science Society of America, United States (1998). * cited by examiner US 9,089,135 B2 1. 2 NEMATICIDAL, INSECTICIDAL AND 2(5H)-one (II-28), 4-(6-chloro-5-fluoropyrid-3-yl)-me ACARCIDAL ACTIVE INGREDIENT thyl(methyl)aminofuran-2(5H)-one (II-29), 4-(5.6- COMBINATIONS COMPRISING dichloropyrid-3-yl)methyl(2-fluoroethyl)aminofuran-2 PYRIDYL-ETHYLBENZAMIDES AND (5H)-one (1'-30), 4-(6-chloro-5-fluoropyrid-3-yl) INSECTICDES methyl (cyclo-propyl)aminofuran-2(5H)-one (II-31), 4 (6-chloropyrid-3-yl)methyl (cyclopropyl)aminofuran The present invention relates to novel active ingredient 2(5H)-one (II-32), 4-(6-chloropyrid-3-yl)methyl combinations which consist of fluopyram and further known (methyl)aminofuran-2(5H)-one (II-33), B-cyfluthrin (II active insecticidal ingredients, and are very Suitable for con 34), transfluthrin (II-35), cyazypyr (II-36), trolling animal pests, such as insects and/or unwanted acarids 10 and/or nematodes, in foliar and soil application and/or in seed chlorantraniliprole (II-37), ethiprole (II-38), sulfoxaflor treatment.
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