1-[pyri(mi)dyl-(2)]-5-hydroxy-pyrazole microbicides

A 1-[2-pyrimidyl]-5-hydroxypyrazole of the formula:

• ##STR57## in which R represents hydrogen;
• or C.sub.6-10 -alkyl optionally substituted with one or more substituents selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkoxy and C.sub.1-6 -alkoxycarbonyl;
• or represents an aralkyl group selected from the group consisting of benzyl, .alpha.-methylbenzyl, .alpha.,.alpha.-dimethylbenzyl, 2-phenylethyl, .alpha.-naphthylmethyl and .beta.-naphthylmethyl each of which is optionally substituted with a substituent selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, halo-C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkylmercapto and cyano;
• or represents C.sub.1-12 -alkoxy;
• R.sub.1 represents C.sub.6-12 -alkyl optionally substituted with one or more substituents selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkoxy and C.sub.1-6 -alkoxycarbonyl;
• or an allyl group;
• or a propynyl, 1-iodo-propynyl or 3,3-dimethylpropynyl group;
• or C.sub.5-7 -cycloalkyl optionally substituted by C.sub.1-4 -alkyl, fluorine or chlorine;
• or represents an aralkyl group selected from the group consisting of benzyl, .alpha.-methylbenzyl, .alpha.,.alpha.-dimethylbenzyl, 2-phenylethyl, .alpha.-naphthylmethyl and .beta.-naphthylmethyl each of which is optionally substituted with a substituent selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, halo-C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkylmercapto and cyano;
• or represents C.sub.1-12 -alkoxy;
• or represents C.sub.1-4 -alkylmercapto optionally substituted by halogen;
• or benzyloxy optionally substituted by one or more substituents selected from the group consisting of halogen and C.sub.1-4 -alkyl;
• or benzylmercapto optionally substituted by one or more substituents selected from the group consisting of halogen and C.sub.1-4 -alkyl;
• or phenoxy optionally substituted by one or more substituents selected from the group consisting of halogen, C.sub.1-4 -alkyl, C.sub.1-2 -halogenoalkyl, cyano, nitro, trifluoromethyl and difluoromethyl;
• or phenylmercapto optionally substituted by one or more substituents selected from the group consisting of halogen, C.sub.1-4 -alkyl, C.sub.1-2 -halogenoalkyl, cyano and nitro;
• or methoxycarbonyl or ethoxycarbonyl;
• or carboxamido, N-methylcarboxamido or N,N-dimethylaminocarboxamido;
• or R.sub.1 together with R forms a divalent alk(en)ylene radical which has 3 to 6 carbon atoms in the chain;
• R.sub.2 represents halogen, nitro, cyano, C.sub.1-4 -alkyl, C.sub.1-2 -halogenoalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, C.sub.1-4 -alkoxycarbonyl, or aminocarbonyl;
• and
• n represents 0 or an integer from 1 to 3, where R.sub.2 represents identical or different radicals when n is 2 or 3.

A method of protecting industrial materials from attack by microbes, said method comprising applying to said industrial materials a microbicidally effective amount of a 1-[2-pyrimidyl]-5-hydroxypyrazole of the formula:

• ##STR58## in which R represents hydrogen;
• or C.sub.6-10 -alkyl optionally substituted with one or more substituents selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkoxy and C.sub.1-6 -alkoxycarbonyl;
• or represents an aralkyl group selected from the group consisting of benzyl, .alpha.-methylbenzyl, .alpha.,.alpha.-dimethylbenzyl, 2-phenylethyl, .alpha.-naphthylmethyl and .beta.-naphthylmethyl each of which is optionally substituted with a substituent selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, halo-C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkylmercapto and cyano;
• or represents C.sub.1-12 -alkoxy;
• R.sub.1 represents C.sub.6-12 -alkyl optionally substituted with one or more substituents selected from the group consisting of chlorine, fluorine,
• C.sub.1-4 -alkoxy and C.sub.1-6 -alkoxycarbonyl;
• or an allyl group;
• or a propynyl, 1-iodo-propynyl or 3,3-dimethylpropynyl group;
• or C.sub.5-7 -cycloalkyl optionally substituted by C.sub.1-4 -alkyl, fluorine or chlorine;
• or represents an aralkyl group selected from the group consisting of benzyl, .alpha.-methylbenzyl, .alpha.,.alpha.-dimethylbenzyl, 2-phenylethyl, .alpha.-naphthylmethyl and .beta.-naphthylmethyl each of which is optionally substituted with a substituent selected from the group consisting of chlorine, fluorine, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, halo-C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkylmercapto and cyano;
• or represents C.sub.1-12 -alkoxy;
• or represents C.sub.1-4 -alkylmercapto optionally substituted by halogen;
• or benzyloxy optionally substituted by one or more substituents selected from the group consisting of halogen and C.sub.1-4 -alkyl;
• or benzylmercapto optionally substituted by one or more substituents selected from the group consisting of halogen and C.sub.1-4 -alkyl;
• or phenoxy optionally substituted by one or more substituents selected from the group consisting of halogen, C.sub.1-4 -alkyl, C.sub.1-2 -halogenoalkyl, cyano, nitro, trifluoromethyl and difluoromethyl;
• or phenylmercapto optionally substituted by one or more substituents selected from the group consisting of halogen, C.sub.1-4 -alkyl, C.sub.1-2 -halogenoalkyl, cyano and nitro;
• or methoxycarbonyl or ethoxycarbonyl;
• or carboxamido, N-methylcarboxamido or N,N-dimethylaminocarboxamido;
• or R.sub.1 together with R forms a divalent alk(en)ylene radical which has 3 to 6 carbon atoms in the chain;
• R.sub.2 represents halogen, nitro, cyano, C.sub.1-4 -alkyl, C.sub.1-2 -halogenoalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylmercapto, C.sub.1-4 -alkoxycarbonyl, or aminocarbonyl;
• and
• n represents 0 or an integer from 1 to 3, where R.sub.2 represents identical or different radicals when n is 2 or 3.