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
2001-08-21
Berch, Mark 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, C544S281000
Reexamination Certificate
active
06277857
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-0 071 792 claims compounds of the general formula
in which R
1
represents alkyl, halogen, alkoxy, cyano, cycloalkyl, aryl, aryloxy, arylthio, aralkyl, 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 claims compounds of the general formula
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 phenyl or naphthyl group; and R
4
represents a 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.
The British patent GB 1,148,629 describes a method for the preparation of s-triazolo[1,5-a]pyrimidines which are substituted in the 7-position by a basic group using 7-alkoxy- or 7-alkylthio-s-triazolo[1,5-a]pyrimidines as educts. However, there is no hint to fungicidal activities disclosed.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula I
in which
R
1
represents an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, bicycloalkyl or heterocyclyl group,
R
2
represents a halogen atom or a group of formula —Y—R
4
, wherein Y represents O, S or NR
5
, with R
4
having the meaning given for R
1
, and R
5
being H or forming with R
4
and the interjacent nitrogen a heterocyclic ring or having the meaning given for R
1
,
R
3
represents hydrogen or an alkyl or aryl group,
L represents halogen or an optionally substituted alkyl or alkoxy group,
A represents N or CR
6
, wherein R
6
has the meaning given for R
3
,
X represents O or S, and
n is 0 or an integer between 1 and 5.
The new compounds show an excellent selective fungicidal activity in various crops.
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 by contacting said plants with a fungicidally effective amount of the new compounds.
It is another object of the invention to provide selective 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
, R
2
, R
3
, A, L and n have the meaning given above for formula I show an excellent fungicidal activity against a broad range of fungi.
In general terms, unless otherwise stated, as used herein the term halogen atom may denote a bromine, iodine, chlorine or fluorine atom, and is especially a bromine, chlorine or fluorine 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.
In general terms, unless otherwise stated herein, the terms alkyl, alkenyl, alkynyl, alkadienyl as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety. As a rule, such radicals have up to 10, in particular up to 6 carbon atoms. Suitably an alkyl moiety has from 1 to 10 carbon atoms, preferably from 2 to 6 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.
In general terms, unless otherwise stated herein, 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 being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, alkoxy, preferably C
1-6
alkoxy, haloalkyl, preferably C
1-6
haloalkyl, haloalkoxy, preferably C
1-6
haloalkoxy groups.
In general terms, unless otherwise stated herein, the term cycloalkyl or cycloalkenyl, as used herein with respect to a radical or moiety refers to a cycloalkyl group having 3 to 8 carbon atoms or a cycloalkenyl group having 5 to 8 carbon atoms, preferably 5 to 7 carbon atoms, in particular cyclopentyl, cyclohexyl or cyclohexenyl being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, alkoxy, preferably C
1-6
alkoxy.
In general terms, unless otherwise stated herein, the term heteroaryl, as used herein with respect to a radical or moiety, refers to an aromatic heterocyclyc group having 5 or 6 ring atoms selected from carbon, nitrogen, oxygen and sulfur, at least one of which being nitrogen, oxygen or sulfur being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, alkoxy, preferably C
1-6
alkoxy, in particular azolyl, triazolyl, triazoly, furanyl, oxazolyl, thienyl, thiazolyl, dithiazolyl, pyridyl or pyrimidyl.
In general terms, unless otherwise stated herein, the term heterocyclyl, as used herein with respect to a radical or moiety, refers to a non-aromatic heterocyclyc group having 5 or 6 ring atoms selected from carbon, nitrogen, oxygen and sulfur, at least one of which being nitrogen, oxygen or sulfur being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, alkoxy, preferably C
1-6
alkoxy, in particular tetrahydropyranyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydropyridyl or tetrahydropyrimidyl.
The invention especially relates to compounds of the general formula I in which any alkyl part of the groups R
1
which may be straight chained or branched, contains 1 to 10 carbon atoms, preferably 2 to 9 carbon atoms, more preferably 3 to 6 carbon atoms, any alkenyl, alkynyl or alkadienyl part of the substituents R
1
contains 2 to 10 carbon atoms, preferably 3 to 9 carbon atoms, more preferably 4 to 6 carbon atoms, any cycloalkyl part of the substituents R
1
contains from 3 to 10 carbon atoms, preferably from 3 to 8 carbon atoms, more preferably from 3 to 6 carbon atoms, and any aryl part of the substituents R
1
contains 6, 10 or 14 carbon atoms, preferably 6 or 10 carbon atoms, and in which each optionally substituted group independently is substituted by one or more halogen atoms or nitro, cyano, 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, alkanoyloxy, preferably C
1-6
alkanoyloxy, haloalkoxy, preferably C
1-6
haloalkoxy, alkylthio, preferably C
1-6
alkylthio, phenyl, halo-, dihalo- or trihalophenyl or pyridyl groups. Any alkyl, alkenyl or alkynyl group may be linear or branched. A halogen atom suitably denotes a fluorine
Pees Klaus-Juergen
Pfrengle Waldemar
American Cyanamid Company
Berch Mark L.
Costello Charles F.
McKenzie Thomas
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