# US 5,703,103 A · Thiazolylpyrazolinones and their use for protecting technical materials

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- Number: US 5,703,103 A
- Document ID: US5703103A
- Status: Granted
- Kind: A
- Application number: 08/716,239
- Filed: 1996-09-24
- Granted: 1997-12-30
- Earliest claimed: 1994-03-31
- Assignees: Bayer Aktiengesellschaft
- Inventors: Lutz Heuer; Peter Wachtler; Martin Kugler; Heinrich Schrage; Klaus Sasse
- Web page: https://patentgrep.com/patent/US5703103A

## CPC

- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- C07D 417/14: containing three or more hetero rings
- C08K 5/47: Thiazoles
- C09D 5/14: Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence)
- D06M 16/00: Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- D21H 21/36: Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- D06M: TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR

## Abstract

The present invention relates to novel thiazolylpyrazolinones, a process for their preparation and their use for the protection of technical materials.

## Claims

### Claim 1

Thiazolylpyrazolinone derivatives of the formula ##STR614## in which R.sup.1, R.sup.2, R.sup.3 independently of each other each represent hydrogen, alkyl or halogen, and
R.sup.4 represents hydrogen or unsubstituted or substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, alkyl (cycloalkyl), alkenyl (cycloalkenyl), alkoxy, alkylthio, aralkoxy, aralkylthio, aralkyl, aryl, hetaryl, aryloxy, hetaryloxy, arylthio, hetarylthio, alkoxycarbonyl, alkoxycarbonalalkyl or cyanoalkyl, or their acid addition products or metal complexes, wherein if R.sup.4 represents substituted hetaryl, then the substituents are selected from the group consisting of halogen, alkyl, alkoxy or alkylthio.

### Claim 2 (depends on 1)

Compounds of the formula (I) according to claim 1, in which ##STR615## R.sup.1, R.sup.2, R.sup.3 denote hydrogen or methyl, R.sup.4 denotes unsubstituted or substituted alkyl, cycloalkyl, alkenyl, aralkyl or aryl.

### Claim 3 (depends on 1)

Compounds of the formula (I) according to claim 1, in which
R.sup.1 denotes hydrogen,
R.sup.2, R.sup.3 denote hydrogen or methyl,
R.sup.4 denotes unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl.

### Claim 4 (depends on 1)

Compounds of the formula (I) according to claim 1, in which
R.sup.1, R.sup.2 and R.sup.3 denote hydrogen,
R.sup.4 denotes unsubstituted or substituted alkyl or cycloalkyl.

### Claim 5 (depends on 1)

Process for the preparation of novel thiazolylpyrazolinone derivatives of the formula (I) according to claim 1, characterized in that thiocarbamoyl compounds of the formula (II) ##STR616## in which R.sup.3 and R.sup.4 have the meanings given above are reacted, in the presence or absence of a solvent or diluent and in the presence or absence of a base, with compounds of the formula (III) ##STR617## in which R.sup.1 and R.sup.2 have the meanings given above and X represents a leaving group.

### Claim 6 (depends on 1)

A composition for protecting a technical material from attack and destruction by a microorganism comprising a protective effective amount of a compound of the formula (I) according to claim 1 and an extender.

### Claim 7 (depends on 1)

A method of protecting a technical material from attack and destruction by a microorganism comprising applying to the technical material or admixing with the technical material a protective effective amount of a compound of the formula (I) according to claim 1.