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Substituted [1,2,4]Triazole and Imidazole Fungicidal Compounds

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Substituted [1,2,4]Triazole and Imidazole Fungicidal Compounds (19) TZZ Z _T (11) EP 2 924 027 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 30.09.2015 Bulletin 2015/40 C07D 249/08 (2006.01) A01N 43/653 (2006.01) (21) Application number: 15158523.9 (22) Date of filing: 10.03.2015 (84) Designated Contracting States: • Boudet, Nadege AL AT BE BG CH CY CZ DE DK EE ES FI FR GB 69493 Hirschberg (DE) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • Müller, Bernd PL PT RO RS SE SI SK SM TR 67227 Frankenthal (DE) Designated Extension States: • Quintero Palomar, Maria Angelica BA ME 68165 Mannheim (DE) Designated Validation States: • Escribano Cuesta, Ana MA 68161 Mannheim (DE) • Lauterwasser, Erica May Wilson (30) Priority: 28.03.2014 EP 14162397 67157 Wachenheim (DE) • Lohmann, Jan Klaas (71) Applicant: BASF SE 67245 Lambsheim (DE) 67056 Ludwigshafen (DE) • Grote, Thomas 67157 Wachenheim (DE) (72) Inventors: • Kretschmer, Manuel • Grammenos, Wassilios 68165 Mannheim (DE) 67071 Ludwigshafen (DE) • Craig, Ian Robert 67063 Ludwigshafen (DE) (54) Substituted [1,2,4]triazole and imidazole fungicidal compounds (57) The present invention relates to compounds of the formula I wherein the variables are defined in the claims and the description, their preparation and uses thereof. EP 2 924 027 A1 Printed by Jouve, 75001 PARIS (FR) EP 2 924 027 A1 Description [0001] The present invention relates to substituted [1,2,4]triazole and imidazole compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi 5 and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions comprising at least one compound I. [0002] DE 3430833 relates to alpha-(ethynylphenyl)-alpha-hydrocarbyl-1 H-azol-1-ethanoles and their use as fungi- cides. PCT/EP2013/076315 relates to triazole and imidazole compounds of the formula I 10 15 [0003] In many cases, in particular at low application rates, the fungicidal activity of the known fungicidal compounds 20 is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi. [0004] Surprisingly, this object is achieved by the use of the inventive substituted [1,2,4]triazole and imidazole com- pounds of formula I having favorable fungicidal activity against phytopathogenic fungi. Accordingly, the present invention relates to the compounds of the formula I 25 30 35 wherein A is CH or N; 40 1 R is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl; wherein the aliphatic moieties of R1 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 1a which independently of one another are selected from: 45 1a R halogen, OH, CN, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy; wherein the cycloalkyl moieties of R 1 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R 1b which independently of one another are selected from: 50 1b R halogen, OH, CN, C 1-C4-alkyl, C1-C4-alkoxy, C 1-C4-halogenalkyl, C3-C6-cycloalkyl, C 3-C6-halogencycloalkyl and C1-C4-halogenalkoxy; 2 R is hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl; 55 wherein the aliphatic moieties of R2 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 2a which independently of one another are selected from: 2a R halogen, OH, CN, C1-C4-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C4-halogenalkoxy; 2 EP 2 924 027 A1 3 R is selected from halogen, CN, 1-CC4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, 3 3a S(O)p(C1-C4-alkyl), whereineach of R is unsubstituted orfurther substitutedby one, two, three or four R ;wherein 3a R is independently selected from halogen, CN, OH, C 1-C4-alkyl, C1-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-hal- 5 ogencycloalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy; m is 0, 1, 2, 3, 4 or 5; 4 R is in each case independently selected from halogen, CN, NO 2, OH, SH, C 1-C6-alkyl, C 1-C6-alkoxy, C 2-C6-alkenyl, 10 C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, S(O)p(C1-C4-alkyl), C(=O)(C1-C4-alkyl), C(=O)(OH), 4 C(=O)(O-C1-C4-alkyl), C(=O)(NH(C1-C4-alkyl)), C(=O)(N(C1-C4-alkyl)2),; wherein each of R is unsubstituted or further substituted by one, two, three or four R 4a wherein 4a R is independently selected from halogen, CN, NO2, OH, C1-C4-alkyl, C1-C4-halogenalkyl, C3-C6-cycloalkyl, 15 C3-C6-halogencycloalkyl, C1-C4-alkoxy and C1-C4-halogenalkoxy; p is 0, 1 or 2; and the N-oxides and the agriculturally acceptable salts thereof. 20 [0005] Compounds I, wherein R2 is different from hydrogen can be obtained from alcohol compounds I (R2=H) by reacting the alcohol compound with R2-LG, wherein LG represents a nucleophilically replaceable leaving group, such as halogen, alkylsulfonyl, alkylsulfonyloxy and arylsulfonyloxy, preferably chloro, bromo or iodo, particularly preferably bromo, preferably in the presence of a base. A, R 1, R2, R3, R4 and m are as defined and preferably defined herein. [0006] Compounds I, wherein R2 is H can be prepared from halo compounds II using transition metal catalysis in a 25 solvent (such as, e.g. THF, DMF, MeCN, NEt3, Et(iPr2)N, pyrrolidine, piperidine, pyridine, diethylamine) using a base (such as NEt3, Et(iPr2)N, pyrrolidine, piperidine, pyridine, diethylamine) and a suitable catalyst like Pd, Cu, Pt, Rh, Ir, Al, Li, Pd(PPh3)4, PdCl2(PPh3)2, PdCl2(dppf), CuI, CuBr, CuCl, LiCl, AlCl3 or mixtures thereof (see e.g. Tetrahedron: Asymmetry, 18(17), 2086-2090; 2007; Angewandte Chemie, International Edition, 43(29), 3814-3818; 2004; Medicinal Chemistry, 53(3), 994-1003; 2010; Organometallics, 25(24), 5768-5773; 2006) as shown in the following scheme: 30 35 40 [0007] Alternatively, compounds II can be transformed to IIa using transition metal catalysis. In a second step, IIa is reacted with an aryl halide "Ar-Hal" ulimately leading to compounds I: 45 50 55 3 EP 2 924 027 A1 5 10 15 20 [0008] Halo compounds II can be prepared starting from known molecules. For example a substituted phenyl Grignard is generated and transformed to a ketone IV (in analogy to the compounds in for example WO 2013/07767). Epoxidation followed by reaction with triazole leads to halogen compound II. 25 30 35 [0009] Alternatively, compounds II can be prepared according to the following scheme: A Grignard is generated and the so obtained acyl compound IVa is chlorinated using a chlorination agent (e.g. SO 2Cl2, NCS, Cl 2). Addition of a metal organic species (e.g. a Grignard compound) leads to a chloro alcohol IIIa that can be subsequently transformed into halo compound II. 40 45 50 [0010] The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, 55 e. g. by treating compounds I with an organic peracid such as metachloroper-benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography. 4 EP 2 924 027 A1 [0011] If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled. 5 [0012] In the following, the intermediate compounds are further described. A skilled person will readily understand thatthe preferences for the substituents, also in particular theones givenin thetables below for the respective substituent s, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein. [0013] Compounds of formula V are at least partially new. Consequently, a further embodiment of the present invention 10 are compounds of formula V (see above), wherein the variables are as defined and preferably defined for formula I herein. [0014] Compounds of formula IV are at least partially new. Consequently, a further embodiment of the present invention are compounds of formula IV (see above), wherein the variables are as defined and preferably defined for formula I herein. [0015] Compounds of formula IVa are at least partially new. Consequently, a further embodiment of the present invention are compounds of formula IVa (see above), wherein the variables are as defined and preferably defined for 15 formula I herein. [0016] Compounds of formula IVb are at least partially new. Consequently, a further embodiment of the present invention are compounds of formula IVa (see above), wherein the variables are as defined and preferably defined for formula I herein.
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