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X Wany (II) Related U.S USOO9029639B2 (12) United States Patent (10) Patent No.: US 9,029,639 B2 Le VezOuet et al. (45) Date of Patent: May 12, 2015 (54) PYRIDAZINE COMPOUNDS FOR FOREIGN PATENT DOCUMENTS CONTROLLING INVERTEBRATE PESTS CA 2 026 131 3, 1991 (75) Inventors: Ronan Le Vezouet, Mannheim (DE); CN 1711255 12/2005 Sebastian Soergel, Ludwigshafen (DE); (Continued) Christian Defieber, Mannheim (DE); OTHER PUBLICATIONS Steffen Gross, Ludwigshafen (DE); Karsten Koerber, Eppelheim (DE); International Preliminary Report on Patentability issued Jan. 10, 2012, from corresponding International Application No. PCT/ Deborah L. Culbertson, Fuquay Varina, EP2010/059333, filed Jul. 1, 2010. NC (US); Douglas D. Anspaugh, Apex, International Search Report completed Aug. 25, 2010, in Interna NC (US) tional Application No. PCT/EP2010/059333, filed Jul. 1, 2010. Milyutin, A.V., et al. “Synthesis properties and biological activity of (73) Assignee: BASFSE, Ludwigshsafen (DE) 3-pyridylamides of 4-aryl-2-hydroxy-4-oxo-2-butenic (Aroylpyruvic) acids'. Pharmaceutical Chemistry Journal, 1997, p. *) Notice: Subject to anyy disclaimer, the term of this 30-33, vol. 31, No. 1. patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. Primary Examiner — Jason Sims (21) Appl. No.: 13/382,225 Assistant Examiner — Ibrahim D Bori (74) Attorney, Agent, or Firm — Brinks Gilson & Lione (22) PCT Filed: Jul. 1, 2010 (57) ABSTRACT (86). PCT No.: PCT/EP2010/059333 The present invention relates to pyridazine compounds of S371 (c)(1), formulae I or II and the salts and N-oxides thereof, (2), (4) Date: Jan. 4, 2012 (87) PCT Pub. No.: WO2011/003796 N (I) x w? Yv PCT Pub. Date: Jan. 13, 2011 ul (65) Prior Publication Data A S. US 2012/O110704 A1 May 3, 2012 R1 R x wany (II) Related U.S. Application Data ls (60) Provisional application No. 61/223,100, filed on Jul. 6, A. S.S. 2009. R (51) Int. Cl. AOIH 5/00 (2006.01) wherein C07D 417/12 (2006.01) A is a substituted or unsubstituted oxazole or thiazole or (Continued) imidazole radical; V is C(R) or N; W is C(R") or N; with the proviso that either (52) U.S. Cl. V or W is N. R. R", R. R" are H, halogen, C-C-alkyl and CPC .............. C07D 417/12 (2013.01); A0IN 43/58 the like: X is S, O or NR'', wherein R'' is selected H, (2013.01); A0IN 43/76 (2013.01); A0IN 43/78 C1-Co-alkyl and the like; X is OR", NR'R'', S(O),R’", (2013.01); C07D 403/12 (2013.01); C07D wherein m is 0, 1 or 2, R is C-C-alkyl, C-C-haloalkyl 413/12 (2013.01) and the like, R, R are H, C, -Ca-alkyl, C-C-haloalkyland (58) Field of Classification Search the like, or R'2b and Ri2c together with the nitrogen atom to CPC CO7D 417/122 CO7D 403/12 CO7D which they are bound form a heterocycle, and R is C-C- 413/12. A0N4358, AON 43/78. A01N alkyl, C1-C4-haloalkyl, Ca-C6-cycloalkyland the like; andR s s is H. CN, C-Cio-alkyl and the like. USPC ....................... 800,298.514/252.05. 544,238. Theling invertebratepresent invention pests, furtherto a method relates for to protecting a method plant for control propa S ee appl1cauonlication fileIlle fIor completelet searcnh historv.n1Story gation material and/or the plants which grow therefrom, to (56) References Cited plant propagation material, comprising at least one com pound according to the present invention, to a method for U.S. PATENT DOCUMENTS treating or protecting an animal from infestation or infection by parasites and to an agricultural composition containing at 5,360,799 A 1 1/1994 Bachy et al. least one compound according to the present invention. 6,747,041 B1 6/2004 Katsuhira et al. (Continued) 23 Claims, No Drawings US 9,029,639 B2 Page 2 (51) Int. Cl. WO WO 2007.121687 11, 2007 AOIN 43/58 (2006.01) WO WO 2007/139856 12/2007 WO WO 2007/139860 12/2007 AOIN 43/76 (2006.01) WO WO 2008, 116898 10, 2008 AOIN 43/78 (2006.01) WO WO 2009,0273.93 3, 2009 CO7D 403/2 (2006.01) WO WO 2009/086303 T 2009 CO7D 413/2 (2006.01) WO WO 2010/017047 2, 2010 WO WO 2010/023.277 3, 2010 WO WO 2010/034.737 4/2010 (56) References Cited WO WO 2010.034738 4/2010 WO WO 2011/003793 1, 2011 U.S. PATENT DOCUMENTS WO WO 2011/OO9804 1, 2011 2006, OO69132 A1 3, 2006 Armel et al. OTHER PUBLICATIONS 392,939. 3. A. 3. 2. Persson, Tobias, et al., “Pyrazole carboxamides and carboxylic acids 2008.0033513 A1 2, 2008 N.A. a. as protein kinase inhibitors in aberrant eukaryotic signal transduc 2008, OO58389 A1 3/2008 Dunkel et al. tion: induction of growth arrest in MCF-7 cancer cells'. Organic & 2009,0163516 A1 6, 2009 Dunkel et al. Biomolecular Chemistry, 2007, pp. 3963-3970, vol. 5. 2009,0176844 A1 7/2009 Dunkel et al. 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WO WO 2007/068377 6, 2007 Final Office Action dated Dec. 9, 2014, from U.S. Appl. No. WO WO 2007/085.188 8, 2007 13/386,473. US 9,029,639 B2 1. 2 PYRIDAZINE COMPOUNDS FOR further amide-derived function in meta-position. These com CONTROLLING INVERTEBRATE PESTS pounds are mentioned to be useful as insecticides. It is an object of the present invention to provide com This application is a National Stage application of Interna pounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum tional Application No.
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