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(12) Patent Application Publication (10) Pub. No.: US 2012/0065063 A1 HALLENBACH Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2012/0065063 A1 HALLENBACH Et Al US 20120065063A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2012/0065063 A1 HALLENBACH et al. (43) Pub. Date: Mar. 15, 2012 (54) 3-ARYL-4-(2,6-DIMETHYLBENZYLIDENE) Publication Classification ISOXAZOL-5(4H)-ONES AS FUNGICIDES (51) Int. Cl. (75) Inventors: Werner HALLENBACH, AOIN 43/80 (2006.01) Monheim (DE); Oliver Guth, C07D 26L/2 (2006.01) Leverkusen (DE); Thomas Seitz, AOIP 9/00 (2006.01) Langenfeld (DE); Heinz-Juergen AOIP 2L/00 (2006.01) Wroblowsky, Langenfeld (DE); AOIP I/00 (2006.01) Philippe Desbordes, Lyon (FR): AOIP 7/02 (2006.01) Ulrike Wachendorff-Neumann, AOIP5/00 (2006.01) Neuwied (DE); Peter Dahmen, AOIP3/00 (2006.01) Neuss (DE); Arnd Voerste, Koln AOIPI3/00 (2006.01) (DE); Peter Lösel, Leverkusen AOIP 7/04 (2006.01) (DE); Olga Malsam, Rosrath (DE); AOIN 25/32 (2006.01) Rachel Rama, AOIP 23/00 (2006.01) Saint-Pierre-la-Palud (FR): Hiroyuki Hadano, Tochigi (JP) (52) U.S. Cl. ......... 504/101: 504/103,504/271; 514/380; 548/243 (73) Assignee: Bayer CropScience AG, Monheim (DE) (57) ABSTRACT (21) Appl. No.: 13/165,971 The invention relates to 3-aryl-4-(2,6-dimethylbenzylidene) isoxazol-5(4H)-ones, to agrochemically active salts thereof, (22) Filed: Jun. 22, 2011 to the use thereof and to methods and compositions for con trolling phytopathogenic harmful fungi and insects in and/or Related U.S. Application Data on plants or in and/or on seed of plants, to processes for (60) Provisional application No. 61/357,759, filed on Jun. producing Such compositions and treated seed, and to the use 23, 2010. thereof for controlling phytopathogenic harmful fungi in agriculture, horticulture and forestry, in animal health, in the (30) Foreign Application Priority Data protection of materials and in the domestic and hygiene sec tor. The present invention further relates to a process for Jun. 22, 2010 (EP) .................................. 1O166827.5 preparing isoxazolone derivatives. US 2012/0065063 A1 Mar. 15, 2012 3-ARYL-4-(2,6-DIMETHYLBENZYLIDENE) in which ISOXAZOL-5(4H)-ONES AS FUNGICIDES 0006 (1) group 1: 0007) R' represents A", 0008 R to Rindependently of one another represent 0001. The invention relates to 3-aryl-4-(2,6-dimethylben hydrogen or A", where furthermore in each case two Zylidene)isoxazol-5(4H)-ones, to agrochemically active salts adjacentradicals R to R together with the carbonatoms thereof, to the use thereof and to methods and compositions to which they are attached may form an unsubstituted or for controlling phytopathogenic harmful fungi and insects in substituted unsaturated or fully or partially saturated and/or on plants or in and/or on seed of plants, to processes for heterocyclic or carbocyclic 5- to 7-membered ring producing Such compositions and treated seed, and to the use which, depending on the ring size, may contain up to 3 thereof for controlling phytopathogenic harmful fungi in further nitrogen atoms or alternatively up to 2 further agriculture, horticulture and forestry, in animal health, in the heteroatoms selected from the group consisting of N, O protection of materials and in the domestic and hygiene sec and S, where two oxygen atoms are not adjacent, tor. The present invention further relates to a process for O preparing isoxazolone derivatives. 0009 (2) group 2: 0002. It is already known that certain 4-ylideneisoxazol-5 R" represents H. (4H)-ones can be used as fungicidal crop protection agents. 0010 Thus, the synthesis of various 4-arylideneisoxazol-5(4H)- 0.011) R' represents A", ones and their biological activity against various fungal dis I0012 R to Rindependently of one another represent eases such as, for example, Erysiphe graminis, Plasmopara hydrogen or A', where furthermore in each case two viticola, Phytophthora infeslans, Pyricularia Oryzae and adjacentradicals R to R together with the carbonatoms Fusarium culmorum has been described (GB-A 1,074,803). to which they are attached may form an unsubstituted or However, in particular at relatively low application rates, the substituted unsaturated or fully or partially saturated fungicidal activity of these compounds is not always Suffi heterocyclic or carbocyclic 5- to 7-membered ring cient. The preparation of 4-arylideneisoxazol-5(4H)-ones which, depending on the ring size, may contain up to 3 and their fungicidal action has likewise been described in J. further nitrogen atoms or alternatively up to 2 further Ind. Chem. Soc. 1971, 54,485. However, the examples shown heteroatoms selected from the group consisting of N, O in this publication are limited to 3-methylarylideneisoxazol and S, where two oxygen atoms are not adjacent, 5(4H)-ones whose fungicidal activity at low application rates O is likewise not always sufficient. Finally, the patent specifi 0013 (3) group 3: cation DD 54366 describes the preparation of 3-substituted 0014 R" and R represent hydrogen, 3-chloro-2-propen-1-ylideneisoxazol-5(4H)-ones. However, (0.015 R represents A", this publication does not mention any fungicidal activity. I0016 RandR independently of one another represent 0003. Since the ecological and economical demands made hydrogen or A', where furthermore the adjacentradicals on modem active compounds, for example fungicides and R to R together with the carbon atoms to which they insecticides, are increasing constantly, for example with are attached may form an unsubstituted or substituted respect to activity spectrum, toxicity, selectivity, application unsaturated or fully or partially saturated heterocyclic or rate, formation of residues and favourable manufacture, and carbocyclic 5- to 7-membered ring which, depending on there can furthermore be problems, for example, with resis the ring size, may contain up to 3 further nitrogenatoms tances, there is a constant need to develop novel fungicidal or alternatively up to 2 further heteroatoms selected and insecticidal compositions which, at least in Some areas, from the group consisting of N, O and S, where two have advantages over the known ones. Oxygen atoms are not adjacent, 0004 Surprisingly, it has now been found that the present and 3-aryl-4-(2,6-dimethylbenzylidene)isoxazol-5(4H)-ones 10017 A' represents halogen, cyano, nitro, OR', SR". achieve at least some aspects of the objects mentioned and are SOR7, SOR7, SONR7R, COR7, C–N OR7, CSR7, therefore suitable for use as fungicides and insecticides. From NR7COR, NR7C(O)SR, NR7C(S)OR, NR7R, the compounds described in GB-A 1,074,803, the present NR7COR, NR7CSR, NR7SOR, OCONR7R, 3-aryl-2,6-dimethylbenzylidene)isoxazol-5(4H)-ones are OCSNR7R, NR7C(O)NR7R, NR7C(S)NR7R, O(CO) distinguished by their surprisingly high activity even at low R7, O(CS)R7, CONR7R, CSNR7R, COR7, C(O)SR7, application rates. C(S)OR7, (CH), OR7, (CH), SR 7, (CH)NR'R'', (CH) 0005. The invention relates to compounds of the formula CO.R. (CH), NRCO.R.C.-Cs-alkyl, C-Cs-alkenyl, (I) C-Cs-alkynyl, C-Cs-haloalkyl, C-Cs-cycloalkyl, C-Cs-cycloalkenyl, tri-C-C-alkyl-silyl phenyl-(di-C- C-alkyl)-silyl, substituted or unsubstituted phenyl or hetaryl or heterocyclyl, substituted or unsubstituted benzyl (I) or —CH2-hetaryl, 10018) R' represents hydrogen or methyl, (0019 R7 and R independently of one another represent hydrogen, unsubstituted or substituted C-C-alkyl, C-Cs-alkenyl, C-Cs-alkynyl, C-Cs-haloalkyl, C-Cs cycloalkyl, tri-C-C-alkyl-silyl, in each case substituted or unsubstituted aryl, —CH2-aryl, hetaryl or —CH2 hetaryl or heterocyclyl, where the two radicals RandR together with this grouping to which they are attached form a 3- to 7-membered unsubstituted or substituted saturated US 2012/0065063 A1 Mar. 15, 2012 or unsaturated cycle which, depending on the ring size, to 3 further nitrogen atoms or alternatively up to 2 further may contain up to 3 further nitrogenatoms or alternatively heteroatoms selected from the group consisting of N, O and S. up to 2 further heteroatoms selected from the group con where two oxygen atoms are not adjacent. sisting of N, O and S, where two oxygen atoms are not R" represents hydrogen, adjacent, R represents A', and 0020 m represents the number 1, 2, 3, 4, 5, 6, 7 or 8, R to R particularly preferably represent hydrogen or A'. to their agrochemically active salts and also to their use for 0029. Moreover, two adjacent radicals R to R together controlling unwanted microorganisms and insects in crop with the carbon atoms to which they are attached particularly protection and in the protection of materials. preferably forman unsubstituted or substituted unsaturated or 0021. The invention further provides for the use of the fully or partially saturated heterocyclic or carbocyclic 5- to compound of the formula (I) in which 7-membered ring which, depending on the ring size, may R" to R represent hydrogen and R represents methyl, contain up to 2 further heteroatoms selected from the group as fungicide and insecticide. consisting of N, O and S, where two oxygen atoms are not 0022. The formula (I) provides a general definition of the adjacent. 3-aryl-(2,6-dimethylbenzylidene)isoxazol-5(4H)-ones R" is hydrogen, according to the invention. Preferred radical definitions are R represents A', and stated below. R to Rindependently of one another very particularly pref erably represent hydrogen or A'. Group (1): 0030. Moreover, two adjacent radicals R to R together with the carbon atoms to which they are attached very par 0023 R' represents A', and ticularly preferably form an unsubstituted or substituted R° to Rindependently of one another preferably represent unsaturated or fully or partially saturated heterocyclic or car hydrogen or A'. bocyclic 5- to 7-membered ring which, depending on the ring 0024 Moreover, two adjacent radicals R to R together size, may contain up to 2 further heteroatoms selected from with the carbon atoms to which they are attached preferably the group consisting of N, O and S, where two oxygenatoms form an unsubstituted or substituted unsaturated or fully or are not adjacent.
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