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(12) United States Patent (10) Patent No.: US 9,028,856 B2 Reid Et Al

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(12) United States Patent (10) Patent No.: US 9,028,856 B2 Reid Et Al USOO9028856B2 (12) United States Patent (10) Patent No.: US 9,028,856 B2 Reid et al. (45) Date of Patent: May 12, 2015 (54) SYNERGISTIC PESTICIDE COMPOSITIONS (52) U.S. Cl. CPC .............. A0IN 65/22 (2013.01); A0IN 25/006 (71) Applicant: Bayer CropScience LP, Research (2013.01); A0IN 43/40 (2013.01); A0IN 51/00 Triangle Park, NC (US) (2013.01); A0IN 43/56 (2013.01); A0IN 47/02 (2013.01); A0IN 47/22 (2013.01); A0IN 53/00 (72) Inventors: Byron L. Reid, Raleigh, NC (US); (2013.01); A0IN 31/14 (2013.01); A0IN3706 Robert B. Baker, Cary, NC (US); (2013.01); A0IN37/10 (2013.01); A0IN 65/12 Nanggang N. Bao, Raleigh, NC (US); (2013.01); A0IN 31/16 (2013.01); A0IN 37/42 Deborah A. Koufas, Clayton, NC (US); (2013.01); A0IN 43/08 (2013.01); A0IN 43/78 Gerald J. Kent, Northfield, NH (US); (2013.01); A0IN 43/88 (2013.01) Peter Baur, Schondorf am Ammersee (58) Field of Classification Search (DE) CPC ............................... A01N 65/12: A01N 61/00 See application file for complete search history. (73) Assignee: Bayer Cropscience LP, Research Triangle Park, NC (US) (56) References Cited (*) Notice: Subject to any disclaimer, the term of this U.S. PATENT DOCUMENTS patent is extended or adjusted under 35 U.S.C. 154(b) by 189 days. 3,042,706 A * 7/1962 Price et al. .................... 560,124 4,320,139 A 3, 1982 Takei et al. (21) Appl. No.: 13/733,007 (Continued) (22) Filed: Jan. 2, 2013 FOREIGN PATENT DOCUMENTS (65) Prior Publication Data AU 2007314150 B2 5, 2008 AU 2007341647 B2 T 2008 US 2013/O183390A1 Jul.18, 2013 (Continued) Related U.S. Application Data OTHER PUBLICATIONS (62) Division of application No. 12/410,840, filed on Mar. Third Party Observation for application No. EP200907268.99 mailed 25, 2009, now Pat. No. 8,404,260. Feb. 27, 2013. (60) Provisional application No. 61/163,206, filed on Mar. (Continued) 25, 2009, provisional application No. 61/072,778, filed on Apr. 2, 2008. Primary Examiner — Patricia A Leith (51) Int. Cl. (74) Attorney, Agent, or Firm — Miles & Stockbridge PC AOIN 65/12 (2009.01) (57) ABSTRACT AOIN 6L/00 (2006.01) AOIN 6.5/22 (2009.01) The present invention relates to compositions that include a AOIN 25/00 (2006.01) combination of one or more pesticides and one or more adju AOIN 43/40 (2006.01) VantS. (Continued) 6 Claims, 57 Drawing Sheets UW Synergy with Deltamethrin against Aedes aegypti mosquito 100 cassessesssssssssssssss 8 O 6 O 4 O -- Deltamethrin (1%) 2 O --Deltamethrin (1%) + UV O r O O2 0.4 O6 O8 1 12 Time (hr) US 9,028,856 B2 Page 2 (51) Int. Cl. JP 10-167906 A 6, 1998 AOINSI/00 (2006.01) JP 2003-55119 A 2, 2003 AOIN 43/56 2006.O1 JP 2004-51631 A 2, 2004 (2006.01) JP 2004-507478 A 3, 2004 AOIN 47/02 (2006.01) JP 2006-525258. A 11, 2006 AOIN 47/22 (2006.01) RU 2O35861 * 5, 1995 AOIN 53/00 (2006.01) W SSA 33 AOIN3L/4 (2006.01) WO Of 40446 6, 2001 AOIN37/06 (2006.01) WO O2, 17721 A2 3, 2002 AOIN37/10 (2006.01) WO O2/O982.30 12/2002 AOIN3L/6 (2006.01) WO 03.01.1031 2, 2003 AOIN 37/42 2006.O1 WO O3O45877 A1 6, 2003 (2006.01) WO 2004/098290 A1 11, 2004 AOIN 43/08 (2006.01) WO 2005OO9129 A1 2/2005 AOIN 43/78 (2006.01) WO 2005058O38 A1 6, 2005 AOIN 43/88 (2006.01) WO 2005099.453 A1 10, 2005 WO 2006/079079 A1 T 2006 WO 2006/089.747 A2 8, 2006 (56) References Cited WO 2007O18659 A1 2/2007 WO 2008/037379 4/2008 U.S. PATENT DOCUMENTS WO 2008052263 A1 5.2008 WO 2008080541 A1 T 2008 4.674.445 A * 6/1987 Cannelongo .................. 119,651 4.888,174 A * 12/1989 Farquharson et al. .......... 514.89 OTHER PUBLICATIONS 5,047,424 A 9, 1991 Puritch et al. 5,334,585 A * 8, 1994 Derian et al. ................... 514,74 International Search Report Based on Application No. PCT/US2009/ 5,346,699 A * 9, 1994 Tiernan et al. ................ 424/405 038349 Mailed May 11, 2009. 5,472,712 A 12/1995 Oshlacket al. Written Opinion Based on Application No. PCT/US2009/038349 5,759,569 A * 6/1998 Hird et al...................... 424/443 Mailed May 11, 2009. 5,798,112 A 8, 1998 Heitz et al. International Preliminary Reporton Patentability Based on Applica $998. A 121 Veroy tion No. PCT/US2009/038349 Mailed October 5, 2010. 6,071,538 A 6/2000 Milstein et al. ............... 424/464 Third Party Observation to Published European Patent Application 6,177.465 B1 ck 1/2001 Tanaka No. 2271210 based on EPO9726899.9-1454 2271210 PCT, 6,337,078 B1 1/2002 Levy ............................. 424/406 US2009038349 mailed Mar. 7, 2013 6,352,704 B1 3/2002 Nicholson et al. males Mar?, 6,395,765 B1 5/2002 Etchegaray Ralph B. Mar. et al., “Synergists for DDT Against Insecticide-Resis 6,500,416 B2 12/2002 Hofer et al. tant House Flies,” Journal of Economic Entomology, 1952, vol. 45, 7,198,800 B1 4/2007 Ko No. 5, pp. 851-860. 7,368,123 B1 5, 2008 Tabuchi et al. Notice of Rejection dated Sep. 3, 2013, issued in Application No. 7,728,011 B2 6/2010 Sirinyan et al. 2011-503045 and English translation thereof. 7,799,737 B2 9/2010 Rosenfeldt et al. European Search Report based on Application No. 09 726 899.9; 2002.0137632 A1 9, 2002 Kawai search completed Oct. 4, 2012. 2002/0177526 A1 11, 2002 Chen et al. Merial MSDS Frontline Top Spot (Oct. 23, 2001). 2003/0194419 A1 10/2003 Sun et al. Ciba TINUVIN 292 Data Sheet (Oct. 2000). 2004O161441 A1 ck 8/2004 Sirinyan et al. Raymond C. Rowe et al., eds., Handbook of Pharmaceutical 2006/00296322005/0244445 A1A1* 11/20052/2006 AndersonHenshaw ..................... 424/405 Excipixcipients (5th5th ed. 2006),2006 pp. 30-31, 79-80,79-80,236-237, 236-237, 414-415,414-415,494 494 2006, O166898 A1 7, 2006 Chen 495,505-506, 2006/0252728 A1 1 1/2006 Sirinyan et al. Sarfaraz K. Niazi, ed., Handbook of Pharmaceutical Manufacturing 2006/0288955 A1* 12/2006 Albright et al. ............... 119,655 Formulations: Liquid Products (vol. 3) (2004), ch.5 “Formulation 2007/0020304 A1 1/2007 Tamarkin et al. Considerations of Liquid Products', pp. 51-58. 2007/O155797 A1 7/2007 Andersch et al. Sartaraz K. Niazi, Handbook of Preformulation: Chemical, Biologi 2007/0298967 A1 12/2007 Kelley cal, and Botanical Drugs (2007); pp. 266, 365. 2008. O146445 A1 6/2008 De Kerpel et al. Hanne Hjorth Tonnesen, ed., Photostability of Drugs and Drug For 2009/0163582 A1 6/2009 Wang et al. mulations (2nd ed.) (2004); pp. 315-316. 2010.0099.717 A1 4/2010 Vermeer et al. Loyd V. Allen, Jr., et al., eds., Pharmaceutical Dosage Forms and Drug Delivery Systems (8th ed.) (2005); pp. 92-141. FOREIGN PATENT DOCUMENTS Mark Gibson, ed., Pharmaceutical Preformulation and Formulation: CN 1433696. A 8, 2003 A Practical Guide from Candidate Drug Selection to Commercial DE 101 17676 10, 2002 Dosage Form (2004); pp. 203-204, 544-546. EP O235979 A1 9, 1987 Beatrice M. Magnusson et al., “Veterinary drug delivery: potential for EP 1112687 A2 T 2001 skin penetration enhancement.” Advanced Drug Delivery Reviews 50 GB 2002635 2, 1979 (2001) 205-227. JP 54-28.818 A 3, 1979 The National Formulary (25th ed.): The Official Compendia of Stan JP 62-56401 A 3, 1987 dards (vol. 1); pp. 1045-1049, 1073-1074, 1168-1170. JP O8151308 * 6/1996 JP 10167906 A * 12/1996 * cited by examiner U.S. Patent May 12, 2015 Sheet 1 of 57 US 9,028,856 B2 Benzenepropanoic acid (5%) Synergy with Imidacloprid against Argentine Ant 100 “ters 80 -0-midacloprid (0.5%) 60 -Himidacloprid (0.5%) BpA (5%) -A-BpA (5%) 40 20 O f O 5 10 15 20 25 Time (hours) Figure 1 Benzenepropanoic acid (1%) Synergy with Imidacloprid against Susceptible German Cockroach 100 YYYYYYYYY. Hay 80 -0-Imidacloprid (0.5%) 60 --Imidacloprid (0.5%) BpA (1%) 5 -A-BpA (1%) e 40 SS 20 O O 5 10 15 20 25 Time (hours) Figure 2 U.S. Patent May 12, 2015 Sheet 2 of 57 US 9,028,856 B2 Oleic Acid (1%) Synergy with imidacloprid against Susceptible German cockroach 100 as 80 -0-midacloprid (0.5%) e -H-Imidacloprid (0.5%) + Oleic Acid (1%) (s 60 -A-Oleic Acid (1%) O e 40 SS 20 O r O 5 10 15 20 25 Time (hours) Figure 3 Oleic Acid (0.1%) Synergy with Imidacloprid against Argentine Ant 1OO s -0-imidacloprid (0.5%) -Himidacloprid (0.5%) + Oleic Acid (0.1%) -A Oleic Acid (0.1%) O 5 1O 15 2O 25 Time (hours) Figure 4 U.S. Patent May 12, 2015 Sheet 3 Of 57 US 9,028,856 B2 Methyl Oleate (5%) Synergy with imidacloprid against Argentine Ant 100 - Hy S 80 5 9 60 -0-midacloprid (0.5%) e -Himidacloprid (0.5%) + Methyl Oleate (5%) 40 -A-Methyl Oleate (5%) O iss 20 O O 5 10 15 20 25 Time (hours) Figure 5 Methyl Oleate (1%) Synergy with imidacloprid against Susceptible German cockroach (T164 Strain) 100 far-Hy 80 60 O e 40 SS -0-mi (0.5% 20 -A-Methyl--Imi E. Oleate -- My (1%) Oleate (1%) O O 5 10 15 20 25 Time (hours) Figure 6 U.S.
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