3-nitroisoxazoles and their use in the protection of materials

Details 3-nitroisoxazoles and their use in the protection of materials 3-nitroisoxazoles and their use in the protection of materials

2003-04-10

2004-12-28

Desai, Rita (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S240000, C548S244000

Reexamination Certificate

active

06835842

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, alkinyl 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, alkinyl 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, alkinyl 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, alkinyl 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.


REFERENCES:
Duranti et al. 1987, “Synthesis and in vitro.”, CAS: 107:20614.*
Beilstein Records, 1995, BRN: 6999109, 6973374, 6973373, and 6967183.*
Beilstein Records, 1988, BRN: 1118358, and 1007342.*
Diamantini et al., 1993, “Nitroisoxazoles by Manganese(IV) oxide oxidation of nitro-4,5-dihydroisoxazoles”, Synthesis, 11:1104-8.*
J. Org. Chem. (month unavailable) 1985, 50, pp. 2736-2739, Kurt Baum and Dangjaw Tzeng, Synthesis and Reactions of Tetranitroethylene.
Tetrahedron Lett. (month unavailable) 1996, 37, pp. 7791-7794, Facile Synthesis of Nitriles from Primary Nitro Compounds Via Nitrolic Acids and Their Esters, Rae Kyu Chang and Kyongtae Kim.
Naturwissenschaften, (month unavailable) 1972, 59, p. 468, K. Eiter, Neue Synthese des Tricosen-(9-cis) (,, Muscalure), eines Attraktivstoffes der Hausfliege.
Tetrahedron Lett. (month unavailable) 1973, 7, pp. 485-486, S. Rossi and E. Durnati, A New Synthesis of 3-Nitroisoxazoles.
Acta Cystallogr., Sect. C. Cryst. Struct. Commun. (month unavailable) 1987, pp. 2011-2013, Don T. Cromer, Robert R. Ryan, Michael D. Coburn and P. Scheda, The Structure of 3,5-Dinitroisoxazole.
Farmaco Ed. Sc., (month unavailable) 1987, 42, pp. 299-306, E. Durnati and C. Balsamini, Sintesi Ed Attivita' Antimicrobica In Vitro Di Derivati 3-Nitroisossazolici.

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