# US 4,396,413 A · Metal salt complexes of 3-isothiazolones as effective biocidal agents

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- Number: US 4,396,413 A
- Document ID: US4396413A
- Status: Granted
- Kind: A
- Application number: 06/369,963
- Filed: 1982-04-19
- Granted: 1983-08-02
- Earliest claimed: 1971-05-12
- Assignees: Rohm and Haas Company
- Inventors: George A. Miller; Ernest D. Weiler
- Web page: https://patentgrep.com/patent/US4396413A

## CPC

- C10M 135/36: the ring containing sulfur and carbon with nitrogen or oxygen
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A61K 8/19: containing inorganic ingredients
- A61K 8/49: containing heterocyclic compounds
- A61Q 17/005: {Antimicrobial preparations}
- C07D 275/03: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C10L 1/2456: {sulfur with oxygen and/or nitrogen in the ring, e.g. thiazoles}
- A61K 2800/524: Preservatives
- A61K 2800/58: Metal complex; Coordination compounds
- C10M 2201/02: Water
- C10M 2219/10: Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M 2219/102: containing sulfur and carbon only in the ring
- C10M 2219/104: containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M 2219/106: Thiadiazoles
- C10N 2010/02: Groups 1 or 11
- C10N 2010/04: Groups 2 or 12
- C10N 2010/06: Groups 3 or 13
- C10N 2010/08: Groups 4 or 14
- C10N 2010/10: Groups 5 or 15
- C10N 2010/12: Groups 6 or 16
- C10N 2010/14: Group 7
- C10N 2010/16: Groups 8, 9, or 10
- C10N 2040/20: Metal working
- C10N 2040/22: with essential removal of material {, e.g. cutting, grinding or drilling}
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

Metal salt complexes of 3-isothiazolones and compositions containing them exhibit useful biocidal properties, including bactericidal, fungicidal, and algaecidal properties.

## Claims

### Claim 1

A biocidal composition which comprises a carrier and a biocidally-effective amount of a metal salt complex of the formula ##STR6## 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.

### Claim 2

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.

### Claim 3

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.

### Claim 4 (depends on 3)

The method of claim 3 wherein the locus is a cosmetic formulation.

### Claim 5

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.

### Claim 6

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.