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(12) Patent Application Publication (10) Pub. No.: US 2010/0261934 A1 FISCHER Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0261934 A1 FISCHER Et Al US 2010O261934A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0261934 A1 FISCHER et al. (43) Pub. Date: Oct. 14, 2010 (54) METHOD FOR PREPARING (30) Foreign Application Priority Data 2,6-DIETHYL-4-METHYLPHENYLACETIC ACD Nov. 4, 2004 (DE) ......................... 1020040531919 (75) Inventors: Reiner FISCHER, Monheim (DE); Publication Classification SEWA his (DE): (51) Int. Cl. ark winem Urewes, C07C 5 L/09 (2006.01) Langenfeld (DE); Dieter Feucht, C07C 5 L/08 (2006.01) Eschborn (DE): Olga Malsam, Rosrath (DE); Guido Bojack, (52) U.S. Cl. ........................................................ 562/496 Wiesbaden (DE); Christian Arnold, Langenfeld (DE). Thomas (57) ABSTRACT Auler, Leichlingen (DE); Jeffrey Marin Hills, Idstein (DE); Heinz The invention relates to novel 2,6-diethyl-4-methylphenyl Kehne, Hofheim (DE); Chris substituted tetramic acid derivatives of the formula (I) Rosinger, Hofheim (DE) Correspondence Address: G (I) STERNE, KESSLER, GOLDSTEIN & FOX P.L. V L.C. A O CHs 1100 NEW YORKAVENUE, N.W. B WASHINGTON, DC 20005 (US) \ -N CH3 (73) Assignee: Bayer CropScience AG, Monheim (DE) O C2H5 (21) Appl. No.: 12/821,831 in which A, B, D and Gare as defined above, to a plurality of (22) Filed: Jun. 23, 2010 processes and intermediates for their preparation and to their O O use as pesticides and/or herbicides, and also to selectively Related U.S. Application Data herbicidal compositions comprising, firstly, the 2,6-diethyl (62) Division of application No. 1 1/666,870, filed on Mar. 4-methylphenyl-substituted tetramic acid derivatives of the 24, 2008, filed as application No. PCT/EP2005/ formula (I) and, secondly, at least one crop plant tolerance 011343 on Oct. 21, 2005. promoter compound. US 2010/0261934 A1 Oct. 14, 2010 METHOD FOR PREPARING in which 2,6-DIETHYL-4-METHYLPHENYLACETIC 0007. A represents hydrogen, represents in each case ACD optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl or alkylthioalkyl or represents optionally substituted cycloalkyl, 0008 B represents hydrogen, alkyl or alkoxyalkyl, or 0001. The invention relates to novel 2,6-diethyl-4-meth 0009. A and B together with the carbonatom to which they ylphenyl-substituted tetramic acid derivatives, to a plurality are attached represent a saturated or unsaturated C-Cs of processes for their preparation and to their use as pesticides ring which optionally contains at least one heteroatom and and/or herbicides. Moreover, the invention relates to novel which is optionally substituted and selective herbicidal active compound combinations compris 0010 D represents hydrogen, ing, firstly, the 2,6-diethyl-4-methylphenyl-substituted tetra O mic acid derivatives and, secondly, a crop plant tolerance 0011. A represents hydrogen or alkyl, promoter compound, which combinations can be used with 0012 B represents hydrogen and 0013 D represents an optionally substituted radical from particularly good results for the selective control of weeds in the group consisting of alkyl, alkenyl, alkynyl, alkoxy various crops of useful plants. alkyl, alkylthioalkyl or optionally cycloalkyl, or 0002 Pharmaceutical properties of 3-acylpyrrolidine-2,4- 0014) A and D together with the atoms to which they are diones are described in the prior art (S. Suzuki et al. Chem. attached represent a saturated or unsaturated cycle which Pharm. Bull. 151120 (1967)). Furthermore, R. Schmierer and optionally contains at least one oxygen or Sulfur atom in the H. Mildenberger (Liebigs Ann. Chem. 1985, 1095) synthe A.D moiety or which is optionally substituted by alkyl, size N-phenylpyrrolidine-2,4-diones. A biological activity of alkoxy or haloalkyl and these compounds has not been described. 00.15 G represents one of the groups 0003 EP-A-0262399 and GB-A-2266 888 disclose com pounds of a similar structure (3-arylpyrrolidine-2,4-diones); however, a herbicidal, insecticidal or acaricidal action of (b) these compounds is not known. Known to have a herbicidal, insecticidal or acaricidal action are unsubstituted, bicyclic 3-arylpyrroli-dine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211), and also substituted monocyclic 3-arylpyr (c) rolidine-2,4-dione derivatives (EP-A-377.893 and EP-A-442 077). 0004 Also known are polycyclic 3-arylpyrrolidine-2,4- dione derivatives (EP-A-442 073), and also 1H-arylpyrroli (d) dine dione derivatives (EP-A-456 063, EP-A-521334, EP-A- 596.298, EP-A-613 884, EP-A-613885, WO 94/01997, WO 95/26954, WO95/20572, EP-A 0 668 267, WO 96/25395, (e) WO 96 35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43275, WO/98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99/43649, WO 99/48869, WO 99/55673, WO 01/09092, WO 01/17972, WO (f) 01/23354, WO 01/74770, WO 03/013249, WO 2004/007448, DE-A-10 239 479, WO 04/065336, WO 04/080962, WO (g) 04/111042, WO 05/044791, WO 05/044796, WO 05/048710, WO 05/049569, DE-A-04 001433). 0005. However, the efficacy and activity spectrum of these compounds, in particular at low application rates and concen trations, are not always satisfactory. Furthermore, the com patibility of these compounds with crops is not always Suffi 0016 in which cient. 0017 E represents a metal ion equivalent or an ammo nium ion, 0006. This invention now provides novel compounds of 0.018 L represents oxygen or sulfur, the formula (I). 0.019 M represents oxygen or sulfur, I0020) R' represents in each case optionally substituted primary or secondary alkyl, alkenyl, alkoxy-alkyl, alkylth (I) ioalkyl or polyalkoxyalkyl or represents in each case optionally halogen-, alkyl- or alkoxy-Substituted cycloalkyl or heterocyclyl or represents in each case optionally substituted phenyl or hetaryl, N \ CH3 (0021) R' represents in each case optionally halogen-sub stituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in each case optionally Substituted cycloalkyl, phenyl or benzyl, I0022 R, R and Rindependently of one another repre sent in each case optionally halogen-substituted alkyl, US 2010/0261934 A1 Oct. 14, 2010 alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent in each case optionally Substi -continued tuted phenyl, benzyl, phenoxy or phenylthio. (1-e): 0023 R and R7 independently of one another represent hydrogen, represent in each case optionally halogen-Sub stituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent in each case optionally Substituted phenyl or benzyl or together with the N atom to which they are attached form an optionally substituted cycle which optionally contains oxygen or Sulfur. 0024 Depending inter alia on the nature of the substi tutents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying composition which, if appropriate, may be separated in a customary manner. The present invention provides both (1-f): the pure isomers and the isomer mixtures, their preparation and use, and compositions comprising them. However, for the sake of simplicity, hereinbelow only compounds of the for mula (I) are referred to, although what is meant are both the pure compounds and, if appropriate, also mixtures having varying proportions of isomeric compounds. 0.025 Including the meanings (b), (c), (d), (e), (f) and (g) of group G, the following principal structures (I-b) to (I-g) result: (1-b): (1-g): (1-c): in which A, B, D, E, L. M. R. R. R. R. R. RandR areas defined above. 0026. Furthermore, it has been found that the novel com pounds of the formula (I) are obtained by one of the processes described below: 0027 (A) compounds of the formula (I-b) shown above in which A, B, D and R' are as defined above are obtained when compounds of the formula (I-a) (1-d): (I-a) US 2010/0261934 A1 Oct. 14, 2010 0028 in which 0056 (E) Compounds of the formula (I-d) shown above in 0029) A, B and Dare as defined above which A, B, D and R are as defined above are obtained 0.030 are reacted when compounds of the formula (I-a) shown above in 0.031 O) with acid halides of the formula (II) which A, B and D are as defined above are in each case reacted 0057 with sulfonyl chlorides of the formula (VII) (II) R SO, Cl (VII) "S RI 0058 in which O 0059 R is as defined above, 0060 if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder. 0032 in which 0061 (F) Compounds of the formula (I-e) shown above in 0033 R' is as defined above and which A, B, D, L. R. and R are as defined above are 0034 Hal represents halogen (in particular chlorine or obtained when compounds of the formula (I-a) shown bromine) above in which A, B and Dareas defined above are in each 0035 or case reacted 0036 B) with carboxylic anhydrides of the formula (III) 0062 with phosphorus compounds of the formula R" CO-O CO-R' (III) (VIII) 0037 in which 0038) R' is as defined above, 4 (VIII) 0039) if appropriate in the presence of a diluent and if R appropriate in the presence of an acid binder. 0040 (C) Compounds of the formula (I-c) shown above in Half which A, B, D, R and M are as defined above and L Ys represents oxygen are obtained when compounds of the formula (I-a) shown above in which A, B and D are as 0063 in which defined above are in each case reacted 0064. L. R* and Rare as defined above and 0041 with chloroformic esters or chloroformic 0065 Hal represents halogen (in particular chlorine or thioesters of the formula (IV) bromine), R’ M.
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