Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-06-16
2000-05-30
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
504156, A01N 4336, A01N 4380
Patent
active
060691611
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the use of aminoisothiazoles as microbicides for protecting industrial materials from being attacked and destroyed by microorganisms. Furthermore, the invention relates to a method for protecting industrial materials from being attacked and destroyed by microorganisms.
Isothiazoles (U.S. Pat. No. 3,761,488, U.S. Pat. No. 4,105,431, U.S. Pat. No. 4,252,694, U.S. Pat. No. 4,265,899, U.S. Pat. No. 4,279,762, U.S. Pat. No. 5,430,046, EP-A 697 409) and benzothiophene derivatives (DE-A 44 11 912), and also mixtures of specific azole derivatives with ammonium compounds (EP-A 533 016), are known to have microbicidal properties. The preparation of some of these compounds is very complicated and their efficacy in particular at low application rates is not always satisfactory.
5-Aminoisothiazoles have been described as coupling components in azo dyes (EP-A 362 708, EP-A 315 898). 5-Aminoisothiazoles (in many cases N-acylated) are also known to have herbicidal (EP-A 640 597, DE-A 24 34 922, DE-A 22 49 162, FR 2132691, U.S. Pat. No. 4,032,321, U.S. Pat. No. 4,032,322, ZA 7202352), bactericidal and virucidal activity (L. Kuczynski et al., Pol. J. Pharmacol. Pharm. (1984), 36(5), 485-491), and to be useful as intermediates for drugs and crop protecting agents.
It is an object of the present invention to provide compounds which can be used as microbicides in the protection of materials, are easily accessible and have a good microbicidal activity.
We have found that this object is achieved by the 5-aminoisothiazoles of the formula I, ##STR1## where R is hydrogen or C.sub.1 -C.sub.4 -alkyl and salts thereof which are very suitable for use as microbicides in the protection of materials. Preference is given to compounds where
In a particularly preferred embodiment, 3-methyl-4-thiocyanato-5-aminoisothiazole (formula Ic), ##STR2## and metal complexes and acid addition salts thereof are used.
The compounds I suitable for use according to the invention are obtained by a reaction sequence known per se from EP-A-640 597 by converting isothiazoles of the general formula II, ##STR3## with the aid of a halogenating agent into the halo compound Ia, where Hal is F, Cl, Br, or I, which is then, if required, converted into the compound Ib, where X' is SCN or CN, by reaction with thiocyanates or cyanides. The preparation of isothiazoles of the general formula II is described for example in DE-A-17 70 819. The preparation of 3-methyl-5-aminoisothiazole was described by A. Adams et al. in J. Chem. Soc. 1959, p. 3061.
The aminoisothiazoles I, per se or in a formulation, are suitable for protecting industrial materials from being attacked and destroyed by microorganisms.
Industrial materials are non-living materials as obtained in industrial processes or non-living materials intended for use in industry. Industrial materials to be protected by the active compounds I from being altered or destroyed by microbes are, for example, dispersions, adhesives, glues, cosmetics, starch solutions, wax emulsions, clay emulsions, paper, sizes, finishes, spin baths, textiles, leather, raw hides, gelatin preparations, bedding putty, joint fillers, wood, paints, articles made from plastic, coolants, drilling oils and other materials which can be attacked or decomposed by microorganisms. The compounds are further suitable for use as slimicides in the paper industry, in recooling plants and air humidifiers. The aminoisothiazoles I are particularly preferably employed in dispersions, such as polymer dispersions and paints.
Microorganisms which may cause a decomposition or an alteration of the industrial materials are, for example, spores, viruses, bacteria, fungi, yeasts, algae and slime organisms. The active compounds or preparations according to the invention preferably act against fungi, bacteria and algae.
By way of example, microorganisms of the following varieties may be mentioned:
Alternaria alternata, Alternaria tenuis, Aspergillus niger, Aureobasidium pullulans, Candida albicans, Chaetomium globosum, Citrobacter freundii,
REFERENCES:
patent: 4032322 (1977-06-01), Gibbons
patent: 4396413 (1983-08-01), Miller et al.
patent: 5538939 (1996-07-01), Muenster et al.
Pol. J. Pharm. 1984, 36, 485-491, Kuczynski et al.
Pest. Sci. 1992, 34, 127-131, Vicentini et al.
Synthesis of some 4-Nitroisothiazoles . . . , Albert et al., Mar. 1980, 385-387.
Reuther Wolfgang
Speakman John-Bryan
Zeller Dieter
BASF - Aktiengesellschaft
Robinson Allen J.
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