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
2001-03-20
Raymond, Richard L. (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
06204269
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, 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.
EP0 550 113-A2 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 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 an optically enriched trifluoromethylalkyl group.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula I
in which
R
1
represents a C
1-4
alkyl group,
CH* indicates a chiral carbon atom,
Hal represents a halogen atom,
L
1
through L
5
each independently represent an hydrogen or halogen atom or an alkyl, alkoxy or nitro group,
characterized in that the enantiomeric excess (ee) of the (S)-enantiomer is at least 70%.
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 another object of the present invention to provide a method for the preparation of the fungicidal compounds of formula I and a method for the resolution of 1,1,1-trifluoroalkyl-2-amines.
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 optically enriched compounds of formula I
in which R
1
, Hal and L
1
through L
5
have the meaning given above having an entantiomeric excess of at least 70% 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.
Hal represents preferably fluorine, chlorine, bromine or iodine, in particular chlorine.
In general terms, unless otherwise stated herein, the terms alkyl, alkoxy 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 alkoxy moiety has from 1 to 6 carbon atoms. A preferred alkoxy moiety is a methoxy or ethoxy group.
The invention especially relates to compounds of the general formula I in which any alkyl part of the group R
1
which may be straight chained or branched, contains up to 6 carbon atoms, preferably up to 4 carbon atoms, more preferably up to 2 carbon atoms, in particular a methyl group.
Included in the scope of the present invention are the diastereomers caused by atropisomerism of compounds of general formula I, 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.
The enantiomeric excess of the (S)-enantiomer is at least 70%, preferably more than 75%, in particular at least 80%.
Preferred are compounds of formula I, in which the phenyl group
The 2,6-difluorophenyl and the 2,4,6-trifluorophenyl group are particularly preferred.
The compounds according to general formula I are oils, gums, or, predominantly crystalline solid materials. They are superior through their valuable fungicidal properties, in particular their enhanced systemicity and enhanced fungicitoxity against rice diseases and powdery mildews. For example, they can be used in agriculture or related fields for the control of phytopathogenic fungi such as
Alternaia solani, Blumeria graminis, Botrytis cinerea, Cercospora beticola, Cladosporium herbarum, Corticium rolfsii, Guignardia bidwellii, Helminthosporium tritici repentis, Leptosphaeria nodorum, Magnaporthe grisea f.
sp.
oryzae, Micronectriella nivalis, Monilinia fructigena, Mycosphaerella fijiensis, Mycosphaerella musicola, Mycosphaerella ligulicola, Mycosphaerella pinodes, Phomopsis viticola, Plasmopara viticola, Podosphaera leucotricha, Pseudopeziza tracheiphila, Phytophthora infestans, Puccinia recondita, Pyrenophora teres, Rhizoctonia solani, Venturia inaequalis, Uncinula necator
and
Scierotinia scierotiorum,
in particular for the residual control of
Blumeria graminis, Plasmopara viticola, Puccinia recondita
and
Pyrenophora teres,
and for the curative control of
Puccinia recondita.
The compounds of general formula I according to the invention possess a high fungicidal activity within a wide concentration range and may be used in agriculture without any difficulties.
Moreover, the compounds according to the invention show enhanced residual control of fungi, in particular of grape downy mildew compared with conventional fungicides.
Good results in terms of control of phytopathogenic fungi are 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 methyl group.
Especially good results in terms of control of phytopathogenic fungi are obtained by using, for example, the following compounds of formula I, wherein the e.e. of the corresponding (S)-enantiomer is at least 80%: 5-chloro-6-(2-chloro-6-fluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,6-difluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-methylphenyl)-7-[2-(1,1,1-trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-fluorophenyl)-7-[2-(1,1,1-trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chlorophenyl)-7-[2-(1,1,1-trifluoro)propylamino]-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-
Albert Guido
Carter Paul
Cotter Henry Van Tuyl
Pees Klaus-Juergen
Pfrengle Waldemar
American Cyanamid Co.
Maurer Barbara V.
Mazzarese Joseph M.
Raymond Richard L.
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