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(12) Patent Application Publication (10) Pub. No.: US 2010/0311593 A1 Fischer Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0311593 A1 Fischer Et Al US 20100311593A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0311593 A1 Fischer et al. (43) Pub. Date: Dec. 9, 2010 (54) HALOALKYLMETHYLENEOXYPHENYL- AOIPI3/00 (2006.01) SUBSTITUTED KETOENOLS C07D 207/00 (2006.01) C07D 305/12 (2006.01) (75) Inventors: Reiner Fischer, Monheim (DE): CD7C 49/00 (2006.01) Thomas Bretschneider, Lohmar C07D 23/00 (2006.01) (DE); Stefan Lehr, Liederbach C07C 229/00 (2006.01) (DE); Eva-Maria Franken, Lyon C07C 69/76 (2006.01) (FR): Olga Malsam, Rosrath (DE); CD7C 24I/00 (2006.01) Arnd Voerste, Koln (DE); Ulrich CD7C 63/04 (2006.01) Görgens, Ratingen (DE); Jan (52) U.S. Cl. ......... 504/219;564/170; 514/622:504/336; Dittgen, Frankfurt (DE); Dieter Feucht, Eschborn (DE); Isolde 504/236; 514/248; 544/235; 540/545; 514/211.08; Hauser-Hahn, Leverkusen (DE); 548/544; 549/319; 568/379: 548/366.4; 560/37; Christopher Hugh Rosinger, 560/76; 560/105:564/149; 562/493 Hofheim (DE); Alfred Angermann, Kriftel (DE) (57) ABSTRACT The invention relates to novel compounds of the formula (I), Correspondence Address: STERNE, KESSLER, GOLDSTEIN & FOX P.L. L.C. (I) 1100 NEW YORKAVENUE, N.W. WASHINGTON, DC 20005 (US) (73) Assignee: Bayer Cropscience AG, Monheim (DE) (21) Appl. No.: 12/639,536 (22) Filed: Mar. 11, 2010 in which W, X, Y, Z and CKE are each as defined above, to several methods and intermediates for preparation thereof (30) Foreign Application Priority Data and to the use thereofas pesticides and/or herbicides. The invention also relates to selective herbicidal composi Mar. 11, 2009 (EP) .................................. O91548883 tions which comprise firstly haloalkylmethyleneoxyphenyl Substituted ketoenols and secondly a compound which Publication Classification improves crop plant compatibility. (51) Int. Cl. The present invention further relates to the enhancement of AOIN 43/46 (2006.01) the action of crop protection compositions comprising espe CD7C 233/00 (2006.01) cially haloalkylmethyleneoxyphenyl-substituted ketoenols, AOIN 37/18 (2006.01) by the addition of ammonium or phosphonium salts and AOIN 43/58 (2006.01) optionally penetration enhancers, to the corresponding com AOIP 5/00 (2006.01) positions, to methods for production thereof and to the use CO7D 487/04 (2006.01) thereof in crop protection as insecticides and/or acaricides CO7D 49.8/04 (2006.01) and/or for preventing undesired plant growth. US 2010/03 11593 A1 Dec. 9, 2010 HALOALKYLMETHYLENEOXYPHENYL used as starting compounds (for example 3-(2-methylphe SUBSTITUTED KETOENOLS nyl)-4-hydroxy-5-(4-fluorophenyl)-A-dihydrofuranone (2)) is likewise described in DE-A-4014.420. Compounds of similar structure with no report of insecticidal and/or acari 0001. The present invention relates to novel haloalkylm cidal efficacy are known from the publication Campbellet al., ethyleneoxyphenyl-substituted ketoenols, to several methods J. Chem. Soc., Perkin Trans. 1, 1985, (8) 1567-76. 3-Aryl for preparation thereof and to the use thereof as pesticides A-dihydrofuranone derivatives with herbicidal, acaricidal and/or herbicides. The invention also provides selective her and insecticidal properties are additionally known from: EP bicidal compositions which comprise firstly haloalkylmeth A-528 156, EP-A-647 637, WO95/26954, WO 96/20 196, yleneoxyphenyl-substituted ketoenols and secondly a com WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 pound which improves crop plant compatibility. 243, WO 97/36 868, WO 98/05 638, WO 98/06 721, WO 0002 The present invention further relates to the enhance 99/16 748, WO 98/25928, WO 99/43649, WO 99/48869, ment of the action of crop protection compositions compris WO 99/55 673, WO 01/23354, WO 01/74. 770, WO 01/17 ing especially haloalkylmethyleneoxyphenyl-substituted 972, WO 04/024688, WO 04/080962, WO 04/111042, WO ketoenols by the addition of ammonium orphosphonium salts 05/092 897, WO 06/000 355, WO 06/029 799, WO 07/048, and optionally penetration enhancers, to the corresponding 545, WO 07/073,856, WO 07/096,058, WO 07/121,868, WO compositions, to methods for production thereof and to the 07/140,881, WO 08/067,911, WO 08/083,950, WO 09/015, use thereof in crop protection as insecticides and/or acari 801, WO 09/039,975. cides and/or for preventing undesired plant growth. I0007 3-Aryl-A-dihydrothiphenone derivatives are 0003 Pharmaceutical properties of 3-acylpyrrolidine-2,4- known from WO95/26 345, 96/25395, WO 97/01 535, WO diones have been described before (S. Suzuki et al. Chem. 97/02243, WO 97/36868, WO 98/05638, WO 98/25928, WO Pharm. Bull. 15 1120 (1967)). In addition, N-phenylpyrroli 99/16748, WO 99/43649, WO 99/48869, WO 99/55673, WO dine-2,4-diones have been synthesized by R. Schmierer and 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). Biologi WO 04/080 962, WO 04/111 042, WO 05/092897, WO cal efficacy of these compounds has not been described. 06/029799 and WO 07/096,058. 0004 EP-A-0262399 and GB-A-2266 888 disclose com 0008 Particular phenylpyrone derivatives unsubstituted pounds of similar structure (3-arylpyrrolidine-2,4-diones), in the phenyl ring have already become known (cf. A. M. which are not, however, known to have any herbicidal, insec Chirazi, T. Kappe uand E. Ziegler, Arch. Pharm. 309, 558 ticidal or acaricidal action. Known compounds with herbi (1976) and K.-H. Boltze and K. Heidenbluth, Chem. Ber. 91, cidal, insecticidal oracaricidal action are unsubstituted, bicy 2849), though no possible usability as a pesticide is reported clic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, for these compounds. Phenylpyrone derivatives substituted in EP-A-415 211 and JP-A-12-053 670) and also substituted the phenyl ring and having herbicidal, acaricidal and insecti monocyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A- cidal properties are described in EP-A-588 137, WO 96/25 377 893 and EP-A-442 077). 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 0005 Additionally known are polycyclic 3-arylpyrroli 97/16 436, WO 97/19941, WO 97/36 868, WO 98/05638, dine-2,4-dione derivatives (EP-A-442 073) and 1H-arylpyr WO99/43649, WO 99/48869, WO 99/55673, WO 01/17972, rolidinedionederivatives (EP-A-456063, EP-A-521334, EP WO 01/74770, WO 03/013249, WO 04/080962, WO 04/111 A-596 298, EP-A-613 884, EP-A-613 885, WO95/01 971, 042, WO 05/092897, WO 06/029799 and WO 07/096,058. WO95/26954, WO95/20572, EP-A-0 668 267, WO 96/25 Additionally described are isomeric pyran-3,5-diones in WO 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 08/071.405 and WO 09/074,314. 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 0009 Particular 5-phenyl-1,3-thiazine derivatives unsub 98/25928, WO 99/24437, WO 99/43649, WO 99/48869, WO stituted in the phenyl ring have already become known (cf. E. 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO Ziegler and E. Steiner, Monatsh.95, 147 (1964), R. Ketcham, 03/013249, WO 03/062244, WO 2004/007448, WO 2004/ T. Kappe and E. Ziegler, J. Heterocycl. Chem. 10, 223 024 688, WO 04/065366, WO 04/080962, WO 04/111042, (1973)), though no possible application as a pesticide is WO 05/044791, WO 05/044796, WO 05/048710, WO reported for these compounds. 5-Phenyl-1,3-thiazine deriva 05/049569, WO 05/066125, WO 05/092897, WO 06/000355, tives Substituted in the phenyl ring and having herbicidal, WO 06/029799, WO 06/056281, WO 06/056282, WO acaricidal and insecticidal action are described in WO94/14 06/089633, WO 07/048.545, DEA 102 00505 9892, WO 785, WO 96/2 5395, WO 96/35 664, WO 97/01 535, WO 07/073,856, WO 07/096,058, WO 07/121,868, WO 07/140, 97/02 243, WO 97/02 243, WO 97/36 868, WO 99/43649, 881, WO 08/067,873, WO 08/067,910, WO 08/067,911, WO WO 99/48869, WO 99/55673, WO 01/17972, WO 01/74770, 08/138,551, WO 09/015,801, WO 09/039,975, WO 09/049, WO 03/013249, WO 04/080 962, WO 04/111 042, WO 851, WO 09/115,262, EP application 08170489). Also known 05/092897, WO 06/029799 and WO 07/096,058. are ketal-substituted 1H-arylpyrrolidine-2,4-diones from 0010. It is known that particular substituted 2-arylcyclo WO 99/16748, and (spiro)-ketal-substituted N-alkoxy pentanediones possess herbicidal, insecticidal and acaricidal alkoxy-substituted arylpyrrolidinediones from JP-A-14 205 properties (cf., for example, U.S. Pat. Nos. 4,283,348; 4.338, 984 and Ito M. et al. Bioscience, Biotechnology and Bio 122; 4,436,666; 4,526,723; 4,551,547; 4,632,698; WO96/01 chemistry 67, 1230-1238, (2003). The addition of safeners to 798: WO 96/03 366, WO 97/14 667 and WO 98/39281, WO ketoenols is likewise known in principle from WO 99/43649, WO99/48869, WO 99/55673, WO 01/17972, WO 03/013249. Also known from WO 06/024411 are herbicidal 01/74770, WO 03/062244, WO 04/080962, WOO4/111042, compositions comprising ketoenols. WO05/092897, WO06/029799, WO07/080,066, WO07/096, I0006. It is known that particular substituted A-dihydro 058, WO 09/019,005, WO 09/019,015 and EP application furan-2-one derivatives possess herbicidal properties (cf.
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