Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-10-23
2003-10-28
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S246000
Reexamination Certificate
active
06638958
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel 3-nitroisoxazoles, a process for their preparation and to the use of novel and known 3-nitroisoxazoles as biocides for protecting industrial materials.
BACKGROUND OF THE INVENTION
Some 3-nitroisoxazoles having alkyl, aryl, hetaryl, alkinyl and alkoxycarbonyl radicals are known; a biological action of the compounds mentioned has not been described. (K. Baum. J. Org. Chem. 1985, 50, 2736; K. Kim, Tetrahedron Lett. 1996, 37, 7791; K. Eiter, Naturwissen-schaften 1972, 59,468; E. Duranti, Tetrahedron Lett. 1973,7, 485).
3,5-Dinitroisoxazoles are known; here, too, an antibacterial action has not been described (D. T. Corner, Acta Crystallogr., Sect. C. Cryst. Struct. Commun. 1987, 43, 2011). Specifically substituted 3-nitroisoxazole-5-carboxaldehyde derivatives are known and in some cases have weak to moderate antibacterial actions (E. Duranti II Farmaco Ed. Sc. 1987, 42, 299).
SUMMARY
The invention relates to a method comprising treating a microbe or a habitat of the microbe with a compound of the formula (I)
wherein R
1
and R
2
independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkynyl or aryl, such that the compound is allowed act on the microbe or its habitat.
In one embodiment, Applicants' invention is directed to a microbicidal composition comprising: (A)a compound of the formula (I)
wherein R
1
and R
2
independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkynyl or aryl, (B) solvents or diluents and, (C) optionally processing auxiliaries, or active compounds, or mixtures thereof.
In one embodiment, Applicants' invention relates to a process for preparing a compound of the formula (I)
wherein R
1
and R
2
independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkynyl or aryl,
in which the process comprising reacting (i) a compound of the formula (II)
R
2
—C≡C—R
1
(II)
wherein R
1
and R
2
are each as defined above with (ii) tetranitroethylene, and optionally in the presence of a diluent.
In another embodiment, Applicants' invention relates to a process for preparing a compound of the formula (I)
wherein R
1
is hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkynyl or aryl, R
2
represents hydrogen. In this embodiment, the process comprises reacting (i) a compound of the general formula (III)
X—CH
2
—C≡C—R
1
(III)
in which R
1
is as defined above and X represents a leaving group, preferably bromine, iodine, chlorine, tosylate or mesylate with (ii) metal nitrites, optionally, in the presence of diluents. These and other features, aspects, and advantages of the present invention will become better understood with reference to the following description and appended claims.
DESCRIPTION
It has now been found that 3-nitroisoxazoles of the general formula
in which R
1
and R
2
independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case optionally substituted alkyl, alkenyl, alkinyl or aryl, have excellent bactericidal action. Owing to their antibacterial and antifungal action, the compounds of the formula (I), alone or in a mixture with one another, are particularly suitable for controlling microorganisms in and on industrial materials.
Moreover, the compounds of the formula (I) have good long-term action and stability in industrial materials.
The formula (I) provides a general definition of the compounds which can be used according to the invention. Preference is given to using compounds of the formula (I) in which
R
1
and R
2
independently of one another each represent hydrogen, halogen, cyano, nitro, or represent in each case straight-chain or branched C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl or C
2
-C
8
-alkynyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, nitro, cyano, aryl, aryloxy, C
1
-C
6
-alkoxy, which is optionally mono- to nonasubstituted by identical or different halogens, C
1
-C
6
-alkylthio, which is optionally mono- to nonasubstituted by identical or different halogens, C
1
-C
6
-acyl, C
1
-C
6
-acyloxy, C
1
-C
6
-alkoxy-carbonyl, amino, which is optionally mono- or disubstituted by identical or different substituents from the group consisting of C
1
-C
4
-alkyl and aryl, or represent C
6
-C
10
-aryl, which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, C
1
-C
5
-alkyl, which is optionally mono- to hexasubstituted by identical or different halogens, C
1
-C
5
-alkoxy, which is optionally mono- to hexasubstituted by identical or different halogens, C
1
-C
5
-alkylthio, which is optionally mono- to hexasubstituted by identical or different halogens, amino, monoalkylamino having straight-chain or branched C
1
-C
6
-alkyl radicals, dialkylamino having identical or different straight-chain or branched C
1
-C
6
-alkyl radicals.
Particular preference is given to using compounds of the formula (I) in which R
1
and R
2
independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, or represent in each case straight-chain or branched C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, cyano, phenyl, naphthyl, phenyloxy, naphthyloxy, C
1
-C
4
-alkoxy, which is optionally mono- to heptasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, C
1
-C
4
-alkylthio, which is optionally mono- to heptasubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, C
1
-C
4
-acyl, C
1
-C
4
-alkoxy-carbonyl, amino, which is optionally mono- or disubstituted by identical or different substituents from the group consisting of C
1
-C
4
-alkyl, phenyl and naphthyl, or represent phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by fluorine, chlorine, bromine, cyano, nitro, C
1
-C
4
-alkyl, which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, C
1
-C
4
-alkoxy, which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, C
1
-C
4
-alkylthio, which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, amino, monoalkylamino having straight-chain or branched C
1
-C
4
-alkyl radicals or dialkylamino having identical or different straight-chain or branched C
1
-C
4
-alkyl radicals.
Very particular preference is given to using compounds of the formula (I) in which R
1
and R
2
independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, represent in each case all isomers of pentyl, hexyl, heptyl and octyl, allyl, vinyl, propargyl, where the alkyl radicals mentioned are in each case optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, cyano, phenyl, phenoxy, 2,4-dichlorophenoxy, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, trifluoromethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, trifluoromethylthio, C
1
-C
4
-acyl, C
1
-C
4
-acyloxy, C
1
-C
4
-alkoxy-carbonyl, amino, which is optionally substituted by identical or different radicals from the group consisting of C
1
-C
4
-alkyl, phenyl and naphthyl, furthermore represent ph
Kretschik Oliver
Kugler Martin
Uhr Hermann
Wachtler Peter
Akorli Godfried R.
Eyl Diderico van
McKane Joseph K.
Shiao Robert
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