Metal salt complexes of 3-isothiazolones as effective biocidal agents

A method for controlling a microorganism which comprises contacting the microorganism with an effective amount of a metal salt complex of the formula ##STR7## wherein Y is a hydrogen atom, an unsubstituted or substituted alkyl group of 1 to 18 carbon atoms, an unsubstituted or substituted alkenyl or alkynyl group of 2 to 18 carbon atoms, an unsubstituted or substituted cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atom ring, an unsubstituted or substituted aralkyl group of up to 10 carbon atoms, or an unsubstituted or substituted aryl group of up to 10 carbon atoms,

• R is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• R' is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• or
• R and R' can be taken together to complete a benzene ring, optionally substituted with one or more halogen atoms, nitro groups, (C.sub.1 -C.sub.4)alkyl groups, cyano groups, or (C.sub.1 -C.sub.4)alkoxy groups;
• M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, lithium, magnesium, manganese, mercury, nickel, silver, sodium, strontium, tin, or zinc;
• X is an anion forming a compound with the cation M, in which the compound has sufficient solubility to form a complex;
• a is the integer 1 or 2;
• and
• n is the integer for which the anion X satisfies the valence of the cation M.

A method for protecting a locus subject to contamination by microorganisms which comprises incorporating into the locus a metal salt complex of the formula ##STR8## wherein Y is a hydrogen atom, an unsubstituted or substituted alkyl group of 1 to 18 carbon atoms, an unsubstituted or substituted alkenyl or alkynyl group of 2 to 18 carbon atoms, an unsubstituted or substituted cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atom ring, an unsubstituted or substituted aralkyl group of up to 10 carbon atoms, or an unsubstituted or substituted aryl group of up to 10 carbon atoms;

• R is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• R' is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• or
• R and R' can be taken together to complete a benzene ring, optionally substituted or one or more halogen atoms, nitro groups, (C.sub.1 -C.sub.4)alkyl groups, cyano groups, or (C.sub.1 -C.sub.4)alkoxy groups;
• M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, lithium, magnesium, manganese, mercury, nickel, silver, sodium, strontium, tin, or zinc;
• X is an anion forming a compound with the cation M, in which the compound has sufficient solubility to form a complex;
• a is the integer 1 or 2;
• and
• n is the integer for which the anion X satisfies the valence of the cation M,
• in an amount which is effective to control the microorganisms.

A cosmetic formulation which comprises a cosmetic ingredient, a carrier, and a microbiocidally effective amount of a metal salt complex of the formula ##STR9## wherein Y is a hydrogen atom, an unsubstituted or substituted alkyl group of 1 to 18 carbon atoms, an unsubstituted or substituted alkenyl or alkynyl group of 2 to 18 carbon atoms, an unsubstituted or substituted cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atom ring, an unsubstituted or substituted aralkyl group of up to 10 carbon atoms, or an unsubstituted or substituted aryl group of up to 10 carbon atoms;

• R is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• R' is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• or
• R and R' can be taken together to complete a benzene ring, optionally substituted with one or more halogen atoms, nitro groups, (C.sub.1 -C.sub.4)alkyl groups, cyano groups, or (C.sub.1 -C.sub.4)alkoxy groups;
• M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, lithium, magnesium, manganese, mercury, nickel, silver, sodium, strontium, tin, or zinc;
• X is an anion forming a compound with the cation M, in which the compound has sufficient solubility to form a complex;
• a is the integer 1 or 2;
• and
• n is the integer for which the anion X satisfies the valence of the cation M.

A method for protecting a seed from attack by microorganisms which comprises dispersing on the surface of the seed a microbiocidally effective amount of a metal salt complex of the formula ##STR10## wherein Y is a hydrogen atom, an unsubstituted or substituted alkyl group of 1 to 18 carbon atoms, an unsubstituted or substituted alkenyl or alkynyl group of 2 to 18 carbon atoms, an unsubstituted or substituted cycloalkyl group of 3 to 12 carbon atoms, having a 3 to 8 carbon atom ring, an unsubstituted or substituted aralkyl group of up to 10 carbon atoms, or an unsubstituted or substituted aryl group of up to 10 carbon atoms;

• R is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• R' is hydrogen, halogen, or a (C.sub.1 -C.sub.4)alkyl group;
• or
• R and R' can be taken together to complete a benzene ring, optionally substituted with one or more halogen atoms, nitro groups, (C.sub.1 -C.sub.4)alkyl groups, cyano groups, or (C.sub.1 -C.sub.4)alkoxy groups;
• M is a cation of barium, cadmium, calcium, chromium, cobalt, copper, iron, lead, lithium, magnesium, manganese, mercury, nickel, silver, sodium, strontium, tin or zinc;
• X is an anion forming a compound with the cation M, in which the compound has sufficient solubility to form a complex;
• a is the integer 1 or 2;
• and
• n is the integer for which the anion X satisfies the valence of the cation M.