USOO859261 OB2 (12) United States Patent (10) Patent No.: US 8,592,610 B2 Bretschneider et al. (45) Date of Patent: *Nov. 26, 2013 (54) SPIROHETEROCYCLICTETRONIC ACID 5,700,758 A 12/1997 Rösch et al. DERVATIVES 5,705,476 A 1, 1998 Hoffarth 5,739,079 A 4/1998 Holdgrin et al. 5,792,755 A 8/1998 Sagenmüller et al. (75) Inventors: Thomas Bretschneider, Lohmar (DE); 5,830,825 A 11/1998 Fischer et al. Reiner Fischer, Monheim (DE); Stefan 5,830,826 A 11/1998 Fischer et al. Lehr, Liederbach (DE); Olga Malsam, 5,972,839 A 10, 1999 Ziemer et al. Rosrath (DE); Arnd Voerste, Cologne 5,994,274 A 11/1999 Fischer et al. 6,114,374. A 9, 2000 Lieb et al. (DE) 6,140,358 A 10/2000 Lieb et al. 6,200,932 B1 3/2001 Fischer et al. (73) Assignee: Bayer CropScience AG, Monheim (DE) 6,235,680 B1 5, 2001 Ziemer et al. 6,251,827 B1 6/2001 Ziemer et al. (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. 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Campbell, A.C., et al., “Synthesis of (E)- and (Z)-Pulvinones,” Jour nal of the Chemical Society, Perkin Transactions 1:1567-1576, Royal (30) Foreign Application Priority Data Society of Chemistry, United Kingdom (1985). Christou, P. “Transformation technology.” Trends in Plant Science May 19, 2009 (EP) ..................................... O9160634 1(12): 423-431. Elsevier Science Ltd., United Kingdom (1996). (Continued) (51) Int. Cl. C07D 307/00 (2006.01) Primary Examiner — Nizal Chandrakumar CO7D 25/00 (2006.01) (74) Attorney, Agent, or Firm — Sterne, Kessler, (52) U.S. Cl. Goldstein & Fox PL.L.C. USPC ............................................. 549/319; 546/16 (57) ABSTRACT (58) Field of Classification Search The present invention relates to novel compounds of the USPC ............................................. 549/319; 546/16 formula (I), (I) See application file for complete search history. 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WO WO91f13972 A1 9, 1991 WO WO91, 19806 A1 12, 1991 * cited by examiner US 8,592,610 B2 1. 2 SPIROHETEROCYCLIC TETRONIC ACID alkoxy, halogen, haloalkyl, haloalkoxy, cyano, nitro or in DERVATIVES each case optionally Substituted aryl or hetaryl, A represents This is a divisional application of application Ser.