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US009 125414B2 (12) United States Patent (10) Patent No.: US 9,125,414 B2 Le VezOuet et al. (45) Date of Patent: Sep. 8, 2015 (54) PYRIDINE DERIVATIVES COMPOUNDS FOR OTHER PUBLICATIONS CONTROLLING INVERTEBRATE PESTS U.S. Environmental Protection Agency, “Insect Repellents: Use and (75) Inventors: Ronan Le Vezouet, Mannheim (DE); Effectiveness”. <http://cfpub.epa.gov/opprefinsect/>, Updated Apr. Sebastian Soergel, Ludwigshafen (DE); 10, 2013, p. 1-2.* Christian Defieber, Mannheim (DE); Merriam-Webster, "Pest'. <http://www.merriam-Webster.com/dic Steffen Gross, Ludwigshafen (DE); tionary pest>, (C) 2013, p. 1-4.* Karsten Koerber, Eppelheim (DE); National Wildlife Federation, “Invertebrates'. <http://www.nwf.org/ wildlife/wildlife-library/invertebrates.aspx>, (C) 1996-2012, p. 1-2.* Deborah L. Culbertson, Fuquay Varina, Pest Control Methods, "Pest control methods: Natural vs. Chemical', NC (US); Douglas D. Anspaugh, Apex, <http://www.pestcontrolmethods.org/>, (C) 2012, p. 1-4.* NC (US) Britannica Online Encyclopedia, "Arthropod”. <http://www.britan nica.com/EBchecked/topic/36943/arthropod, 2013, p. 1-5.* (73) Assignee: BASFSE, Ludwigshafen (DE) Texas A&M Agrilife Extension, “Order Homoptera'. <https://in (*) Notice: Subject to any disclaimer, the term of this sects.tamu.edu/fieldguide/orders/homoptera.html>, 1999, p. 1.* patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 79 days. (21) Appl. No.: 13/386,473 Primary Examiner — Tracy Vivlemore Assistant Examiner — Monica Shin (22) PCT Filed: Jul. 15, 2010 (74) Attorney, Agent, or Firm — Brinks Gilson & Lione (86). PCT No.: PCT/EP2010/06O243 (57) ABSTRACT S371 (c)(1), The present invention relates to methods and uses of com (2), (4) Date: Jan. 23, 2012 pounds of formulae I or II and the salts and N-oxides thereof, (87) PCT Pub. No.: WO2011/009804 PCT Pub. Date: Jan. 27, 2011 (I) X3 (65) Prior Publication Data US 2012/O122681 A1 May 17, 2012 XI 21 Related U.S. Application Data --, N R3 (60) Provisional application No. 61/228.205, filed on Jul. k . 24, 2009. (II) X3 (51) Int. Cl. AOIN 43/40 (2006.01) AOIP 7/04 (2006.01) X2 2 (Continued) s N R3 (52) U.S. Cl. CPC ................ A0IN 43/80 (2013.01); A0IN 43/50 R2 (2013.01); A0IN 43/76 (2013.01); A0IN 43/78 (2013.01); C07D401/12 (2013.01); C07D wherein 413/12 (2013.01); C07D 417/12 (2013.01) A is a substituted or unsubstituted 5-membered heterocyclic (58) Field of Classification Search radical; CPC ....... A01N 43/80: A01N 43/78: A01N 43/50: X is S, O or NR", wherein R' is selected from H, C, -Co A01N 43/76; C07D 413/12: C07D 417/12: alkyl and the like; X is OR, NRR, S(O).R. X is CO7D 401A12 OR, NR'R', S(O)R’, wherein m is 0, 1 or 2, R is See application file for complete search history. C-C-alkyl, C-C-haloalkyl and the like, R, R are H. C1-C4-alkyl, C-Ca-haloalkyl and the like:X is alonepair or (56) References Cited oxygen; R', R and Rare, interalia, hydrogen, and R' is H. U.S. PATENT DOCUMENTS C-Co-alkyl and the like. The present invention further relates to a method for controlling invertebrate pests, to a 5,360,799 A 1 1/1994 Bachy et al. method for protecting plant propagation material and/or the 6,747,041 B1 6/2004 Katsuhira et al. plants which grow therefrom, to plant propagation material, (Continued) comprising at least one compound according to the present invention, to a method for treating or protecting an animal FOREIGN PATENT DOCUMENTS from infestation or infection by parasites and to an agricul tural composition containing at least one compound accord CA 2 026 131 3, 1991 CN 1711255 12/2005 ing to the present invention. (Continued) 4 Claims, No Drawings US 9,125.414 B2 Page 2 (51) Int. Cl. WO WO 2006,133926 12/2006 teN ty C WO WO 2007/0465502007/046548 4/2007 (2006.01) WO WO 2007/065664 6, 2007 AOIN 43/76 (2006.01) WO WO 2007/068373 6, 2007 AOIN 43/78 (2006.01) WO WO 2007/068375 6, 2007 CO7D 40/12 (2006.01) WO WO 2007/068377 6, 2007 WO WO 2007/085.188 8, 2007 CO7D 413/2 (2006.01) WO WO 2007.121687 11, 2007 C07D 417/12 (2006.01) WO WO 2007/139856 12/2007 WO WO 2007/139860 12/2007 (56) References Cited WO WO 2008, 116898 10, 2008 WO WO 2009,0273.93 3, 2009 U.S. PATENT DOCUMENTS WO WO 2009/086303 T 2009 WO WO 2010/017047 2, 2010 2006/0069132 A1 3f2006 Armel et al. WO WO 2010/023.277 3, 2010 20070203148 A1 8/2007 Dunkel et al. WO WO 2010/034.737 4/2010 2007/0275980 A1 11, 2007 Yoshida et al. WO WO 2010.034738 4/2010 2008.0033513 A1 2/2008 Man et al. WO WO 2011/003793 1, 2011 2008/0058389 A1 3f2008 Dunkel et al. WO WO 2011/003796 1, 2011 2009/0163516 A1 6/2009 Dunkel et al. 2009,0176844 A1 7, 2009 Dunkel et al. OTHER PUBLICATIONS 38885.8 A. 3. R; etal Cranshaw et al., “Spider Mites”. Colorado State University Exten sion, Fact Sheet No. 5.507. Insect Series: Home and Garden, Nov. FOREIGN PATENT DOCUMENTS 2006, p. 1-3.* Technicide, “Pest Control', <http://technicide.com/Pest CN 1927838 3, 2007 Controld, (C) 2006, p. 1-2.* CN 101062916 10/2007 Buzzle, "Wast Insect Control: Wasp Traps and Repellent”. <http:// CN 101062919 10/2007 www.buzzle.com/articles/wasp-insect-control-wasp-traps-andrepel EP O 419944 4f1991 lent.html>, Dec. 8, 2007, p. 1-2.* EP O573883 12/1993 Shelton et al., “Effects of Weeds on the Diversity and Abundance of EP 0606175 T 1994 Insects in Soybeans.” Environmental Entomology, vol. 12, No. 2, EP O 89.1975 1, 1999 EP 1188 745 3, 2002 Apr. 1983, p. 296–298.* EP 2263455 12/2010 Bayhan et al., “Effect of temperature on development, mortality, JP 10195072 7, 1998 fecundity, and reproduction of Aphis rumicis L. (Homoptera: JP 20011596,10 6, 2001 Aphididae) on broadleaf dock (Rumex obtusifolius) and Swiss chard JP 2001348378 12/2001 (Beta vulgaris vulgaris var, cida).” J Pest Sci (2006) 79: 57-61.* JP 2004-269515 9, 2004 International Preliminary Report on Patentability issued Jan. 24. JP 2004331541 11, 2004 2012, from corresponding International Application No. PCT/ JP 2005-532367 10/2005 EP2010/060243, filed Jul 15, 2010. JP 2006.52O373 9, 2006 International Search Report completed Mar. 18, 2011, in Interna JP 2007/77106 3, 2007 tional Application No. PCT/EP2010/060243, filed Jul. 1, 2010. JP 2008-285482 11, 2008 Milyutin, A.V., et al. “Synthesis properties and biological activity of WO WO 98.54154 12/1998 3-pyridylamides of 4-aryl-2-hydroxy-4-oxo-2-butenic WO WO99/48868 9, 1999 WO WOOO,29398 5, 2000 (Aroylpyruvic) acids'. Pharmaceutical Chemistry Journal, 1997, p. WO WOO1/OO575 1, 2001 30-33, vol. 31, No. 1. 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No. 13/382,229. WO WO 2005, O75411 8, 2005 Office Action dated Feb. 25, 2014, from U.S. Appl. No. 13/382,225, WO WO 2006/O15860 2, 2006 filed Jan. 4, 2012. WO WO 2006/045522 5, 2006 WO WO 2006/074445 T 2006 * cited by examiner US 9,125,414 B2 1. 2 PYRONEDERVATIVES COMPOUNDS FOR CONTROLLING INVERTEBRATE PESTS (I) X3 This application is a National Stage application of Interna N tional Application No. PCT/EP2010/060243 filed Jul. 15, XI 21 2010, which claims the benefit of U.S. Provisional Applica tion No. 61/228,205 filed Jul. 24, 2009, the entire contents of --, S R3 which are hereby incorporated herein by reference. R2 The present invention relates to pyridine compounds which 10 (II) can be used for combating and/or controlling invertebrate X3 pests, in particular arthropod pests. The invention also relates to a method for controlling invertebrate pests by using these X2 21 compounds. The present invention also relates to seed and to an agricultural and Veterinary composition comprising said 15 ls compounds. A 1s R3 R2 BACKGROUND OF INVENTION wherein Invertebrate pests and in particular arthropods and nema A is an oxazole or thiazole or imidazole or isoxazole or todes destroy growing and harvested crops and attack wooden isothiazole radical of the formulae A1a, A1, A2a, A2, dwelling and commercial structures, thereby causing large A3a, A3 economic loss to the food supply and to property. While a 25 large number of pesticidal agents are known, due to the ability A1 of target pests to develop resistance to said agents, there is an R41 ongoing need for new agents for combating invertebrate pests Such as insects, arachnids and nematodes.