3-phenyl-4-pyri(mi)dinyl-1h-pyrazoles and their use as fungicides

摘要

Phenylpyri(mi)dinylazole compounds (A) and their salts, are new. Phenylpyri(mi)dinylazole compounds (A) of formulae (I) and (II), and their salts, are new. In formula (I): X1 : CH or N; R1 : e.g. 1-benzothiophen-4-yl, 1-benzothiophen-7-yl, 1-benzofuran-4-yl, 1-benzofuran-7-yl, 1,3-benzodioxol-4-yl or 1,3-benzodioxol-5-yl (all optionally one or more times substituted); R2 : e.g. CN, nitro, halo, 2-9C-heterocyclyl or H; R3 : e.g. 1-6C-alkyl, 2-6C-alkenyl, 2-6C-alkynyl or 3-6C-cycloalkyl (all optionally one or more times substituted); R4 : e.g. 1-6C-alkyl, 3-8C-cycloalkyl, 2-6C-alkenyl, 6-14C-aryl, 2-9C-heterocyclyl or 2-9C-heteroaryl (all optionally one or more times substituted), H, halo or CN; and R5, R6 : e.g. 1-6C-alkyl, 6-14C-aryl, S-(1-4C-alkyl), S(O)-(1-6C-alkyl) or C(O)-(1-6C-alkyl) (all optionally one or more times substituted), H, F, Cl, Br, CN, nitro, OH or SH. In formula (II): X1 : CH or N; R1 : e.g. isoquinolin-5-yl, isoquinolin-8-yl, 1-benzothiophen-4-yl, 1-benzofuran-7-yl or 1,3-benzodioxol-5-yl (all optionally one or more times substituted); R2 : e.g. 1-6C-(halo)alkyl, 3-6C-(halo)cycloalkyl, 2-9C-heterocyclyl or H; R301 : e.g. 1-6C-alkyl, 2-6C-alkenyl, 3-6C-allenyl, 2-6C-alkynyl, 3-8C-cycloalkyl, 1-6C-alkoxy, 2-9C-heterocyclyl, 2-9C-oxo-heterocyclyl or heteroaryl (all optionally one or more times substituted); R401 : e.g. NR12R13 or C(O)NR12R13; R5, R6 : e.g. 1-6C-alkyl, 3-6C-cycloalkyl, 2-6C-alkenyl, 2-6C-alkynyl, 6-14C-aryl, S(O)-(1-6C-alkyl) or C(O)-(1-6C-alkyl) (all optionally one or more times substituted); R12 : e.g. C(S)R15, C(O)R15 or SO 2R15; R13 : e.g. 1-6C-alkyl, 3-6C-cycloalkyl, 2-6C-alkenyl or 2-9C-heteroaryl (all optionally one or more times substituted) or H; and R15 : e.g. 1-6C-alkyl, 3-6C-cycloalkyl, 2-6C-alkenyl, 2-6C-alkynyl or 2-9C-heteroaryl (all optionally one or more times substituted). Full Definitions are given in the DEFINITIONS (Full Definitions) Field. Independent claims are included for: (1) (hetero)aryl-pyrazole compounds (X) of formulae (XA) and (XB) and their salts; (2) (hetero)aryl-pyrazole compounds (XI) of formulae (XIA) and (XIB) and their salts, where (XI) exclude 1-({4-[1-(2,2-difluoroethyl)-3-(trimethylstannyl)-1H-pyrazol-4-yl]pyrimidin-2-yl}amino)propan-2-ol; (3) (hetero)arylamine-pyrazole compounds (III) of formulae (IIIA) and (IIIB) and their salts, where (III) exclude 4-[3-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl]pyridin-2-amine, 4-[3-(4-chlorophenyl)-5-methyl-1H-pyrazol-4-yl]pyridin-2-amine, 4-[3-(4-methoxyphenyl)-5-methyl-1H-pyrazol-4-yl]pyridin-2-amine, 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidin-2-amine, 4-(5-methyl-3-phenyl-1H-pyrazol-4-yl)pyrimidin-2-amine and [4-(2-aminopyrimidin-4-yl)-3-(3-chloro-5-hydroxyphenyl)-1H-pyrazol-1-yl]acetonitrile; (4) substituted pyrazole compounds (V) of formulae (VA) and (VB) and their salts, where (V) exclude 1-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole; and (5) substituted bromo-pyrazole compounds (VI) of formulae (VIA) and (VIB), where (VI) exclude the compounds, in which R3 and R301 are H, CH 3or C(CH 3) 3. PG : tetrahydro-2H-pyran-2-yl; M3 : tributylstannyl or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl; PG1 : tetrahydro-2H-pyran-2-yl or 2-(trimethylsilyl)ethoxymethyl; and B(OR1A) 2 : -B(O-isopropyl) 2or -B(OH) 2. [Image] [Image] [Image] [Image] ACTIVITY : Fungicide; Antibacterial. MECHANISM OF ACTION : None given. The fungicidal activity of (A) against Botrytis cinereawas tested in cucumber plants. The results showed that 4-[3-(4-fluorophenyl)-1-(2-methylpropyl)-1H-pyrazol-4-yl]pyridine (500 ppm) exhibited an activity of 100%.