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(12) United States Patent (10) Patent No.: US 8,592,610 B2 Bretschneider Et Al

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(12) United States Patent (10) Patent No.: US 8,592,610 B2 Bretschneider Et Al 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. FOREIGN PATENT DOCUMENTS This patent is Subject to a terminal dis CA 1162 071 A1 2, 1984 claimer. CA 2671 179 A1 6, 2008 (21) Appl. No.: 13/616,437 (Continued) OTHER PUBLICATIONS (22) Filed: Sep. 14, 2012 Baur et al., 1997, Pesticide Science 51, 131-152.* Baur, P. et al., “Polydisperse Ethoxylated Fatty Alcohol Surfactants (65) Prior Publication Data as Accelerators of Cuticular Penetration. 1. Effects of Ethoxy Chain Length and the Size of the Penetrants.” Pestic. Sci. 51:131-152, SCI. US 2013/OO12384 A1 Jan. 10, 2013 United Kingdom (1997). Braun, H.-P. et al., “The general mitochondrial processing peptidase Related U.S. Application Data from potato is an integral part of cytochrome c reductase of the respiratory chain.” The EmboJournal 11 (9):3219-3227. Oxford Uni (62) Division of application No. 12/783.236, filed on May versity Press, United Kingdom (1992). 19, 2010, now Pat. No. 8,318,956. 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. (56) References Cited U.S. PATENT DOCUMENTS 2,842,476 A 7, 1958 Schreiber 4,623,727 A 11, 1986 Hibele 4,639,266 A 1, 1987 Heubach et al. 4,844,734. A 7, 1989. Iwasaki et al. in which W, X, Y, Z, G, A and t have the meanings given 4,881,966 A 1 1/1989 Nyffeler et al. 4,888,049 A 12/1989. Iwasaki et al. above, 4,891,057 A 1/1990 Sohn et al. to a plurality of processes and intermediates for their prepa 4,902,340 A 2, 1990 Hubele ration and to their use as pesticides and/or herbicides. 4,944,790 A 7, 1990 Moser et al. Moreover, the invention relates to selective herbicidal com 5,013,659 A 5, 1991 Bedbrook et al. positions comprising, firstly, the spiroheterocyclic tetronic 5,094,681 A 3, 1992 Krämer et al. acid derivates and, secondly, a crop plant compatibility-im 5,215,570 A 6, 1993 Burckhardt et al. proving compound. 5,262,383 A 11/1993 Fischer et al. The present invention furthermore relates to increasing the 5,314,863. A 5, 1994 Löher et al. activity of crop protection compositions comprising in par 5,380,852 A 1/1995 Schlitze et al. ticular phenyl-substituted bicyclooctane-1,3-dione derivates 5,401,700 A 3, 1995 Sohn et al. by adding ammonium salts or phosphonium salts and, if 5,462.912 A 10, 1995 Hioki et al. appropriate, penetrants, to the corresponding compositions, 5,500,367 A 3, 1996 Hain et al. 5,516,750 A 5, 1996 Willms et al. to processes for their preparation and to their use in crop 5,538,937 A 7, 1996 HaSebe et al. protection as insecticides and/or acaricides and/or for pre 5,610,122 A 3, 1997 Fischer et al. venting unwanted plant growth. 5,689,046 A 11/1997 Schröder et al. 8 Claims, No Drawings US 8,592,610 B2 Page 2 (56) References Cited WO WO92fOO377 A1 1, 1992 WO WO92f1 1376 A1 7, 1992 U.S. PATENT DOCUMENTS WO WO92, 14827 A1 9, 1992 WO WO92, 16108 A1 10, 1992 6.288,102 B1 9/2001 Hagemann et al. WO WO95/17817 * 6, 1995 6,316,486 B1 1 1/2001 Lieb et al. 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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.
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