Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-09-24
2001-06-05
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S263000
Reexamination Certificate
active
06242451
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to certain triazolopyrimidine compounds, a process for their preparation, compositions containing such compounds, a method for combating a fungus at a locus comprising treating the locus with such compounds and their use as fungicides.
EP-A-0071792 claims compounds of the general formula
in which R
1
represents alkyl, halogen, alkoxy, cyano, cycloalkyl, aryl, aryloxy, arylthio, aralkyl, arylthio, arylalkyl, arylalkyloxy or arylalkylthio each optionally substituted by halogen or alkoxy; or (R
1
)
n
represents a benzene, indane or tetrahydronaphthalene ring fused with the phenyl ring, aromatic moieties in the above groups being optionally substituted by alkyl, alkoxy, halogen or cyano; n is 1 or 2; R
2
and R
3
are each hydrogen, alkyl or aryl, A represents a nitrogen atom or a CR
4
group, and R
4
is as R
2
but can also be halogen, cyano or alkoxycarbonyl or together with R
3
can form an alkylene chain containing up to two double bonds. The compounds are said to be active against various phytopathogenic fungi, especially those of the phycomycete class. However evidence of fungicidal activity is only provided for these compounds against
Plasmopara viticola,
a member of the oomycete class of fungi.
U.S. Pat. No. 5,593,996 embraces compounds of the general formula 1
in which R
1
represents an optionally substituted alkyl, alkenyl, alkadienyl, cycloalkyl, bicycloalkyl or heterocyclyl group; R
2
represents a hydrogen atom or an alkyl group; or R
1
and R
2
together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring; R
3
represents an optionally substituted aryl group; and R
4
represents a hydrogen or halogen atom or a group —NR
5
R
6
where R
5
represents a hydrogen atom or an amino, alkyl, cycloalkyl or bicycloalkyl group and R
6
represents a hydrogen atom or an alkyl group. Thus, compounds in which R
3
is a trichlorophenyl group are generally covered by this patent application. These compounds are said to be active against fungi which are members of the ascomycetes class such as
Venturia inaequalis
and of the hyphomycetes class such as
Alternaria solani
and
Botrytis cinerea.
However, there is no single compound disclosed in which R
3
is a phenyl group, trisubstituted in the 2,4,6-positions by fluorine and/or chlorine atoms.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula I
in which
R
1
and R
2
each independently represent a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or
R
1
and R
2
together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring;
R
3
, R
4
and R
5
each independently represent a fluorine or a chlorine atom, provided that at least one of R
3
, R
4
and R
5
is a chlorine atom.
X represents a halogen atom.
The new compounds show an excellent fungicidal activity in various crops, in particular against
Pyricularia oryzae
(
Magnaporthe grisea
) the causative agent of rice blast disease.
It is an object of the present invention to provide novel, selective fungicidal compounds.
It is also an object of the invention to provide methods for controlling an undesired fungus, in particular
Pyricularia oryzae
the causative agent of rice blast disease, by contacting said plants with a fungicidally effective amount of the new compounds.
It is another object of the invention to provide fungicidal compositions containing the new compounds as active ingredients.
These and other objects and features of the invention will be more apparent from the detailed description set forth hereinbelow, and from the appended claims.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
It has surprisingly been found that the compounds of formula I
in which R
1
to R
5
and X have the meaning given above for formula I show excellent fungicidal activity against a broad range of fungi, in particular against
Pyricularia oryzae,
the causative agent of rice blast disease.
As used herein, the term halogen atom includes a bromine, iodine, chlorine or fluorine atom, and especially a bromine, chlorine or fluorine atom, in particular a chlorine atom.
Optionally substituted moieties may be unsubstituted or have from one up to the maximal possible number of substituents. Typically, 0 to 2 substituents are present. The term ‘optionally substituted’, as used herein with reference to a group, means that the group is substituted by one or more halogen atoms, or by nitro, cyano, hydroxy, alkyl (preferably C
1-6
alkyl), cycloalkyl (preferably C
3-6
cycloalkyl), cycloalkenyl (preferably C
3-6
cycloalkenyl), haloalkyl (preferably C
1-6
haloalkyl), halocycloalkyl (preferably C
3-6
halocycloalkyl), alkoxy (preferably C
1-6
alkoxy), haloalkoxy (preferably C
1-6
haloalkoxy), trialkylsilyl (preferably tri-C
1-4
alkylsilyl), phenyl, halo- or dihalo-phenyl or pyridyl groups.
The terms alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety. Preferably, such radicals or moieties have up to 10, in particular up to 6, carbon atoms. Suitably, an alkyl moiety has from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms. A preferred alkyl moiety is an ethyl or, especially, a methyl group. Suitably, an alkenyl moiety has from 2 to 6 carbon atoms. A preferred alkenyl moiety is allyl or, especially, a 2-methylallyl group. Suitably, a haloalkyl moiety has from 1 to 6 fluoro atoms. Preferred haloalkyl moieties includes the 2,2,2-trifluoroethyl and 1,1,1-trifluoroprop-2-yl groups.
The term aryl, as used herein with respect to a radical or moiety, refers to an aryl group having 6, 10 or 14 carbon atoms, preferably 6 or 10 carbon atoms, in particular phenyl optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, and/or alkoxy, preferably C
1-6
alkoxy.
The term heteroaryl, as used herein with respect to a radical or moiety, refers to a heteroaryl group having 5 or 6 ring atoms selected from carbon, nitrogen, oxygen and sulphur, at least one of which is nitrogen, oxygen or sulphur, in particular pyridyl, pyrimidyl, pyrazolyl or thienyl.
The term cycloalkyl, as used herein with respect to a radical or moiety, refers to a cycloalkyl group having 3 to 8 carbon atoms, preferably 5 to 7 carbon atoms, in particular cyclopentyl optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, and/or alkoxy, preferably C
1-6
alkoxy.
The term bicycloalkyl, as used herein with respect to a radical or moiety, refers to a bicycloalkyl group having 5 to 10 carbon atoms, preferably 6 to 9 carbon atoms, in particular bicycloheptyl optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, and/or alkoxy, preferably C
1-6
alkoxy.
The term heterocyclyl, as used herein with respect to a radical or moiety, refers to a saturated heterocyclyl group having 5 or 6 ring atoms selected from carbon, nitrogen, oxygen and sulphur, at least one of which is nitrogen, oxygen or sulphur, optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, and/or alkoxy, preferably C
1-6
alkoxy. Pyrrolodinyl, pyrrazolidinyl, piperidinyl, piperazinyl and morpholin-4-yl are particularly preferred.
The invention especially relates to compounds of formula I in which any alkyl or haloalkyl part of the groups R
1
or R
2
, which may be straight chained or branched, contains up to 10 carbon atoms, preferably 1 to 9 carbon atoms, and more preferably 2 to 6 carbon atoms, any alkenyl or alkynyl part of the substituents R
1
or R
2
contains up to 10 carbon atoms, preferably 2 to 9 carbon atoms, and more preferably 3 to 6 carbon atoms, any cycloalkyl part of the substituents R
1
or R
2
contains from 3 to 10 carbon atoms, preferably from 3 to 8 carbon atoms, more preferably from 3 to 6 carbon atoms, any bicycloalkyl part of the subst
Maurer Barbara V.
Patel Sudhaker B.
Raymond Richard L.
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