Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-03-13
2002-03-19
Higel, Floyd D. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S236000, C514S376000
Reexamination Certificate
active
06359142
ABSTRACT:
The present invention relates to novel sulphonyloxazolones, to a process for their preparation and to the use for controlling undesirable microorganisms.
Certain sulphonyloxazolones, such as, for example, 4-[(4-chlorophenyl)sulphonyl]-3-(2,4,6-trimethyl-phenyl)-1,2,4-oxadiazol-5(4H)-one, have already been disclosed (cf. Zh. Org. Khim. 27 (1991), 1262-1270). However, a biological action of these compounds has hitherto not been described.
Novel sulphonyloxazolones of the formula
in which
R
1
represents alkyl or represents optionally substituted heterocyclyl or represents a radical of the formula
in which
R
3
represents halogen, alkyl or phenyl,
R
4
represents hydrogen or alkyl and
R
5
represents alkyl or optionally substituted phenyl, and
R
2
represents alkyl,
have now been found.
Furthermore, it has been found that sulphonyloxazolones of the formula (I) are obtained, when oxazolones of the formula
in which
R
2
is as defined above,
are reacted with sulphonyl halides of the formula
R
1
—SO
2
—Hal (III)
in which
R
1
is as defined above and
Hal represents chlorine or bromine,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it has been found that the sulphonyloxazolones of the formula (I) have very good microbicidal properties and can be used for controlling undesirable micro-organisms in crop protection and in agriculture.
Surprisingly, the sulphonyloxazolones of the formula (I) according to the invention have better activity against undesirable microorganisms, in particular against fungi, than the constitutionally most similar prior-art substances of the same direction of action.
The formula (I) provides a general definition of the substances according to the invention.
R
1
preferably represents alkyl having 1 to 4 carbon atoms or represents a heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and/or sulphur, where this radical may contain a keto or imino group and may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, hydroxyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, carbamoyl, alkylaminocarbonyl having 1 to 4 carbon atoms in the alkyl moiety, dialkylaminocarbonyl having 1 to 4 carbon atoms in the individual alkyl moieties, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties and cycloalkyl having 3 to 6 carbon atoms.
R
1
furthermore preferably represents a radical of the formula
R
3
preferably represents fluorine, chlorine, bromine, alkyl having 1 to 6 carbon atoms or represents phenyl.
R
4
preferably represents hydrogen or alkyl having 1 to 6 carbon atoms.
R
5
preferably represents alkyl having 1 to 6 carbon atoms or represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, nitro, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-halogenoalkyl having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenoalkoxy having 1 to 5 identical or different halogen atoms, C
1
-C
6
-halogenoalkylthio having 1 to 5 identical or different halogen atoms, cyano and cycloalkyl having 3 to 6 carbon atoms.
R
2
preferably represents alkyl having 1 to 6 carbon atoms.
R
1
particularly preferably represents methyl, ethyl, propyl, isopropyl or represents furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, pyrrolidinyl, piperidinyl or morpholinyl, where these radicals may be mono-, di- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, carbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, hydroxyiminomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl and ethoximinoethyl.
R
1
furthermore particularly preferably represents a radical of the formula
R
3
particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or phenyl.
R
4
particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
R
5
particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert.-butyl, or represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-pro pylthio, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and cyclohexyl.
R
2
particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
R
1
very particularly preferably represents methyl, ethyl, isopropyl or represents furyl, thienyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, 1,2,4-triazinyl, pyrrolidinyl, piperidinyl or morpholinyl, where these radicals may be mono-, di- or trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, carbamoyl, methyl, ethyl, n- or i-propyl, cyclopropyl, methoxy, ethoxy, tri-fluoromethyl, difluoromethoxy, trifluoromethoxy, acetyl, methoxycarbonyl, ethoxycarbonyl, hydroxyiminomethyl, hydroxyiminoethyl, methoximino-methyl, ethoxyiminomethyl, methoximinoethyl and ethoximinoethyl.
R
1
furthermore very particularly preferably represents a radical of the formula
R
3
very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl or phenyl.
R
4
very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl or n-butyl.
R
5
very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl, or represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoro-ethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, cyano, cyclopropyl, cyclopentyl and cyclohexyl.
R
2
also very particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl or tert-butyl.
The meanings of the substituents given above can be combined with one another as desired Moreover, individual definitions may not be applicable.
Using 5-cyano4-ethyl-3H-[1,3)-oxazol-2-one and 3,5-dimethylisoxazole-4-sulphonyl chloride as starting materials, the course of the process according to the invention can be illustrated by the equation below.
The formula (II) provides a general definition of the oxazolones required as starting materials for carrying out the process according to the invention. In this formula, R
2
preferably has those meanings which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for this radi
Assmann Lutz
Jautelat Manfred
Stenzel Klaus
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Gil Joseph C.
Harmuth Raymond J.
Higel Floyd D.
Saeed Kamal
LandOfFree
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