Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-03-19
2001-07-03
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...
C514S272000, C514S275000, C514S257000, C544S262000, C544S263000, C544S242000
Reexamination Certificate
active
06255309
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 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. EP 0 550 113-A2 claims compounds of the 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
1
is a trifluoromethylalkyl group are generally embraced by this patent application. However, there is no single compound disclosed in which R
1
is a trifluoromethylalkyl group.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula I
in which
R
1
represents a hydrogen or a methyl group;
R
2
represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl or phenyl group;
Hal represents a halogen atom; and
L
1
through L
5
each independently represent an hydrogen or halogen atom or an alkyl, alkoxy or nitro group, provided that at least one of L
1
through L
5
represents a nitro or alkoxy group.
The new compounds show 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 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 novel compounds of formula I
in which R
1
, R
2
, Hal and L
1
through L
5
have the meaning given above for formula I show excellent fungicidal activity against a broad range of fungi.
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. Hal preferably represents a chlorine atom.
Optionally substituted moieties may be unsubstituted or have from one up to the maximal possible number of substituents. Typically, 0 to 3 substituents are present.
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.
The invention especially relates to compounds of formula I in which any alkyl part of the groups R
1
and/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
and/or R
2
contains up to 10 carbon atoms, preferably up to 9 carbon atoms, more preferably up to 6 carbon atoms, and in which each optionally substituted group independently is substituted by one or more halogen atoms or nitro, cyano, 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 halogen atom suitably denotes a fluorine, chlorine or bromine atom.
The invention especially relates to compounds of formula I, in which R
1
represents a hydrogen atom, a C
1-10
alkyl or a phenyl group, in particular a hydrogen atom or a methyl group.
Included in the scope of the present invention are (R) and (S) isomers and atropisomers of compounds of formula I, which have a chiral center or in which the substituents L
1
or L
1
and L
2
are different from L
5
or L
5
and L
4
, and the racemates thereof, and salts, N-oxides and acid addition compounds.
Particularly interesting activity has been found in (S)-isomer compounds of formula I wherein the group —CH(CF
3
)R
1
is chiral.
Another preferred embodiment of the present invention are the compounds of formula I, wherein R
2
represents a hydrogen atom or a C
1-10
alkyl group or a C
3-10
alkenyl group.
Those compounds of formula I in which at least one of R
1
and R
2
represents a hydrogen atom are particularly preferred.
The compounds according to formula I may be oils, gums, or, predominantly crystalline solid materials. They exhibit valuable fungicidal properties, especially enhanced systemicity and enhanced fungicitoxity against rice diseases and powdery mildews compared to conventional fungicides known in the art. For example, they can be used in agriculture or related fields for the control of phytopathogenic fungi such as
Alternaria solani, Botrytis cinerea, Cercospora beticola, Cladosporium herbarum, Corticium rolfsii, Erysiphe graminis, Helminthosporium tritici repentis, Leptosphaeria nodorum, Micronectriella nivalis, Monilinia fructigena, Mycosphaerella ligulicola, Mycosphaerella pinodes, Pyricularia grisea
f.sp. oryzae,
Rhizoctonia solani, Venturia inaequalis, Uncinula necator
and
Sclerotinia sclerotiorum,
in particular for the control of
Uncinula necator, Pyricularia grisea
f.sp. oryzae and
Rhizoctonia solani.
The compounds of formula I according to the invention possess a high fungicidal activity within a wide concentration range and may be used in agriculture without significant difficulties.
Moreover, the compounds according to the invention show enhanced residual control of fungi, in particular of grape powdery mildew compared with conventional fungicides.
Good control of phythopathogenic fungi may be obtained with a compound as defined in formula I wherein:
at least one of L
1
and L
5
represents a halogen atom; and/or
R
1
represents a hydrogen atom or a methyl group.
Especially good results in terms of control of phytopathogenic fungi are obtained by using, for example, the following compounds of formula I: 5-chloro-6-(4-methoxyphenyl)-7-(2,2,2-trifluoroethylamino)-[1,2,4]triazolo[1,5-a&rsq
Albert Guido
Cotter Henry Van Tuyl
Krummel Guenter
May Leslie
Pees Klaus-Juergen
American Cyanomid Co.
Maurer Barbara V.
Patel Sudhaker B.
Raymond Richard L.
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