Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-04-17
2001-06-12
Morris, Patricia L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S263200
Reexamination Certificate
active
06245793
ABSTRACT:
The present invention relates to novel oxiranyl-triazolinethiones, to a process for their preparation and to their uses as microbicides.
It is already known that numerous azolylmethyl-oxirane derivatives have fungicidal properties (cf. EP-A 0 094 564, EP-A 0 196 038 and WO-A 96-38 440). Thus, for example, 3-(2-chloro-phenyl)-2-(4-fluoro-phenyl)2-[(4,5-dihydro-5-thiono-1,2,4-triazol-1-yl)-methyl]-oxirane can be used for controlling fungi. The activity of this substance is good; however, it is sometimes unsatisfactory at low application rates.
This invention, accordingly, provides novel oxiranyl-triazolinethiones of the formula
in which
R
1
represents alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5Halogen atoms, optionally halogen-substituted cycloalkyl having 3 to 7 carbon atoms, naphthyl or phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, nitro, phenyl, phenoxy, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5Halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5Halogen atoms and halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5Halogen atoms,
R
2
represents phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5Halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5Halogen atoms and halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5Halogen atoms and
R
3
represents alkoxyalkyl, isopropyl or n-dodecyl.
The substances according to the invention contain two asymmetrically substituted carbon atoms and can therefore be obtained in the form of diastereomers or enantiomers. The present invention relates both to the individual isomers and to their mixtures.
Furthermore, it has been found that oxiranyl-triazolinethiones of the formula (I) or (Ia) are obtained when oxirane derivatives of the formula
in which
R
1
and R
2
are each as defined above are reacted with isocyanates of the formula
R
3
—NCO (III),
in which
R
3
is as defined above,
if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent.
Finally, it has been found that the novel oxiranyl-triazolinethiones of the formula (I) or (Ia) have very good microbicidal properties and can be used both in crop protection and in the protection of materials for controlling undesirable microorganisms.
Surprisingly, the oxiranyl-triazolinethiones of the formula (I) or (Ia) according to the invention have better microbicidal activity, in particular fungicidal activity, than the constitutionally most similar prior-art compounds of the same direction of action. Thus, the substances according to the invention surpass 3-(2-chloro-phenyl)-2-(4-fluoro-phenyl)-2-[(4,5-dihydro-5-thiono-1,2,4-triazol-1-yl)-methyl]-oxirane with respect to the fungicidal properties.
The formula (I) or (Ia) provides a general definition of the oxiranyl-triazolinethiones according to the invention.
R
1
preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl, cycloalkyl having 3 to 6 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine, preferably represents naphthyl or preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio,
R
2
preferably represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluorometboxy, difluoromethoxy and trifluoromethylthio, and
R
3
preferably represents alkoxyalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety and also preferably represents isopropyl or n-dodecyl.
Particular preference is given to oxiranyl-triazolinethiones of the formula (I) or (Ia) in which
R
1
represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, nitro, phenyl, phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxy and trifluoromethylthio,
R
2
represents phenyl which may be mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloromethyl, trifluorometboxy, difluoromethoxy and trifluoromethylthio,
and
R
3
represents alkoxyalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety and also represents isopropyl or n-dodecyl.
The substituent definitions mentioned can be combined with one another at will. Moreover, individual definitions may not apply.
The oxirane derivatives required as starting materials for preparing the substances according to the invention can be present in the “thiono” form of the formula
or in the tautomeric “mercapto” form of the formula
It is therefore possible that the substances according to the invention can be derived both from the “thiono” form of the formula (II) and from the “mercapto” form of the formula (IIa). This means that the substances according to the invention are either present as substances of the formula
or of the formula
or as mixtures of the formulae (I) and (Ia).
Examples of substances according to the invention which may be mentioned are the oxiranyl-triazolinethiones listed in the table below.
TABLE 1
R
1
R
2
R
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—CH
2
—CH
2
—O—CH
3
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—CH
3
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
—(CH
2
)
3
—O—C
2
H
5
Exner Otto
Hillebrand Stefan
Jautelat Manfred
Kugler Martin
Mauler-Machnik Astrid
Bayer Aktiengesellschaft
Gil Joseph C.
Morris Patricia L.
Zurcher Jackie Ann
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