N- (2- (hydroxymethyl) phenyl) -1H-pyrazol-4-carboxamide derivatives and related compounds as microbicidal active ingredients for use in plant protection and protection of materials
Carboxamides of the formula (I) in which R1 represents hydrogen, C1-C8 alkyl, C1-C6 alkyl sulfonyl, C1-C6 alkyl sulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C3-C8 cycloalkyl; C1-C6 halogenoalkyl, C1-C4-thio haloalkyl, C1-C4-sulfinyl halogenoalkyl, C1-C4-sulfonyl alkyl, C1-C4 halogenoalkoxy-C1-C4 alkyl, C3-C8 halocycloalkyl with, respectively, 1 to 9 fluorine atoms , chlorine and / or bromine; formyl, formyl-C1-C3 alkyl, (C1-C3 alkyl) carbonyl-C1-C3 alkyl, (C1-C3 alkoxy) carbonyl-C1-C3 alkyl; halogen- (C1-C3 alkyl) carbonyl-C1-C3 alkyl, halogen- (C1-C3 alkoxy) carbonyl-C1-C3 alkyl with, respectively, 1 to 13 fluorine, chlorine and / or bromine atoms; (C1-C8 alkyl) carbonyl, (C1-C8 alkoxy) carbonyl, (C1-C4 alkoxy-C1-C4 alkyl) carbonyl, (C3-C8 cycloalkyl) carbonyl; (halogeno C1-C6 alkyl) carbonyl, (halogenoalkoxy C1-C6) carbonyl, (halogeno-C1-C4 alkoxy-C1-C4 alkyl) carbonyl, (halogenocycloalkyl C3-C8) carbonyl with, respectively, 1 to 9 fluorine atoms, chlorine and / or bromine; or -C (>; = O) C (>; = O) R2, -CONR3R4 or -CH2NR5R6, R2 represents hydrogen, C1-C8 alkyl, C1-C8 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C3-C8 cycloalkyl ; C1-C6 halogenoalkyl, C1-C6 halogenoalkoxy, C1-C4 halogenoalkoxy-C1-C4 alkyl, C3-C8 halogenocycloalkyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R3 and R4 independently represent each other, respectively, hydrogen, C1-C8 alkyl, C1-C4 alkoxy-C1-C4 alkyl, C3-C8 cycloalkyl; C1-C8 halogenoalkyl, C1-C4 halogenoalkoxy-C1-C4 alkyl, C3-C8 halogenocycloalkyl with, respectively, 1 to 9 fluorine, chlorine and / or bromine atoms, R3 and R4, in addition, together with the nitrogen atom to which they are attached, form a heterocycle with 5 to 8 saturated ring atoms, if necessary substituted one or more times, in the same or different way, with halogen or C1-C4 alkyl, the heterocycle 1 or 2 additional non-adjacent heteroatoms may contain the oxygen, sulfur or NR7, R5 and R6 series, independently of one another, represent hydrogen, C1-C8 alky