Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-12-08
2001-10-02
Shah, Mukund J. (Department: 1611)
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
06297251
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
Plasmo-para viticola,
a member of the oomycete class of fungi.
U.S. Pat. No. 5,593,996 embraces 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 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 trifluorophenyl 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 hypho-mycetes class such as
Alternaria solani
and
Botrytis cinerea.
However, there is no single compound disclosed in which R
3
is a 2,4,6-trifluorophenyl group.
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, tricycloalkyl or heterocyclyl group, or
R
1
and R
2
together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring,
Hal represents a halogen atom.
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
and Hal 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, in particular a chlorine atom.
Hal represents preferably a fluorine, chlorine, bromine or iodine 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.
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 6 carbon atoms, preferably from 1 to 3 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.
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.
In general terms, unless otherwise stated herein, 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 being nitrogen, oxygen or sulphur.
In general terms, unless otherwise stated herein, 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 cyclohexyl 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 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 being nitrogen, oxygen or sulphur 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 pyrrolodinyl, pyrrazolidin, piperidinyl, piperazinyl or morpholin-4-yl.
The invention especially relates to compounds of the general formula I in which any alkyl part of the groups R
1
or R
2
, which may be straight chained or branched, contains up to 10 carbon atoms, preferably up to 9 carbon atoms, more preferably up to 6 carbon atoms, any alkenyl or alkynyl part of the substituents R
1
or R
2
contains up to 10 carbon atoms, preferably up to 9 carbon atoms, more preferably up 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, and any aryl part of the substituent R
1
or R
2
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, 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. Any alkyl, alkenyl or alkynyl group may be linear or branched. A 4- to 6-membered heterocyclic group may be any heterocyclic group with 4 to 6 ring atoms, interrupted by one or more heteroatoms selected from sulfur, nitrogen, and oxygen, preferably oxygen. A halogen atom suitably denotes a fluorine, chlorine or bromine atom.
The invention especially relates to compounds of the general formula I in which R
1
represents a straight-chained or branched C
1-10
alkyl, in particular a branched C
3-10
alkyl group, a C
3-8
cycloalkyl, a C
3-8
cycloalkyl-C
1-6
alkyl, C
1-10
alkoxy-C
1-6
alkyl, a C
1-10
haloalk
Albert Guido
Pees Klaus-Juergen
American Cyanamid Co.
Balasubramanian Venkataraman
Maurer Barbara V.
Shah Mukund J.
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