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
2002-04-30
Ford, John M. (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
06380202
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to certain triazolopyrimidine compounds having a fluoro-substituted heterocyclyl group attached to the 7-position, 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.
U.S. Pat. No. 5,593,996 claims compounds of the general formula
in which 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. However, there is no hint to such triazolopyrimidines, in which the heterocyclic ring formed by R
1
and R
2
with the adjacent nitrogen atom is substituted by at least one fluoro atom or fluoro alkyl group. Moreover, there is no indication that such a substitution pattern would achieve an enhancement of the systemicity of the resulting compounds.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula I
in which
R
1
and R
2
together with the interjacent N atom represent a heterocyclic group being substituted by at least one fluorine atom or at least one fluoroalkyl group,
Hal represents a halogen atom
L
1
through L
5
each independently represent an hydrogen or halogen atom or an alkyl or nitro group.
The new compounds combine excellent selective fungicidal activity in various crops with high systemicity.
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
, L
1
through L
5
and Hal have the meaning given above for formula I show an excellent fungicidal activity against a broad range of fungi and high systemicity.
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 term alkyl, 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.
In general terms, unless otherwise stated herein, the term heterocyclyl, as used herein with respect to the group formed by R
1
, R
2
and the interjacent nitrogen atom, refers to a nitrogen containing heterocyclyl group having 2 to 8 carbon atoms and optionally one or two oxygen or sulfur atoms, preferably 4 to 7 carbon atoms and optionally 1 oxygen atom, in particular 1H-azirid-1-yl, oxazirid-1-yl, 1H-azetid-1-yl, pyrrolid-1-yl, piperid-1-yl, piperazin-1-yl or morpholin-1-yl being substituted by one or more fluoro atoms or by one or more fluoroalkyl, preferably C
1-6
fluoroalkyl, in particular fluoromethyl groups.
Particularly preferred are those compounds of formula I, in which R
1
and R
2
together with the interjacent N atom form a group of formula
wherein
X represents a fluorine atom or a C
1-4
fluoroalkyl group, and m is an integer from 1 to 4, in particular in which m is 1 or 2 and X represents a fluorine atom or a fluoromethyl or trifluoromethyl group.
Most preferred are the 4-fluoropiperidyl, the 4,4-difluoropiperidyl, the 4-trifluoromethylpiperidyl and the 4-fluoromethylpiperidyl group.
Preferably at least one of the substituents L
1
through L
5
, in particular L
1
and/or L
5
, is different from hydrogen. L
1
is preferably a fluorine or chlorine atom or a methyl, methoxy or trifluoromethoxy group. The other substituents are preferably selected from hydrogen or fluorine.
Particularly preferred are compounds of formula I, in which the phenyl group of formula
Most preferred are the 2-chloro-6-fluorophenyl and the 2,4,6-trifluorophenyl group.
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 fungitoxicity against a broad range of phytopathogenic fungi. For example, they can be used in agriculture or related fields for the control of phytopathogenic fungi such as
Venturia inaequalis, 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, Phytophthora infestans, Puccinia recondita, Pyricularia grisea f.sp. oryzae, Rhizoctonia solani, Monographella nivalis and Sclerotinia sclerotiorum,
in particular for the control of
Alternaria solani, Botrytis cinerea, Erysiphe graminis, Puccinia recondita
and
Venturia inaequalis.
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 systemicity and residual control of fungi compared with known triazolopyrimidine derivatives.
Good results in terms of control of phytopathogenic fungi are obtained with a compound as defined in formula I wherein:
Hal represents a chloro atom;
R
1
and R
2
together with the interjacent nitrogen atom represent a piperid-1-yl group being substituted by one fluoroalkyl, preferably straight chained or branched C
1
-C
3
-fluoroalkyl group, in particular fluoromethyl, or one or two fluorine atoms.
In particular preferred are the compounds of formula IA,
in which
L
1
, L
3
and L
5
each independently represent hydrogen, fluorine or chlorine, methyl, trifluoromethoxy at least one of which being different from hydrogen, and
m is 0 or 1.
Especially good results in terms of control of phytopathogenic fungi are obtained by using, for example, the following compounds of formula I: 5-chloro-7-N-(4-fluoropiperid-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-N-(4-fluoromethylpiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-N-(3-fluoropiperid-1-yl)-6-(pentafluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-N-(3-fluoropiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-N-(4,4-difluoropiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-N-(4-fluoromethylpiperid-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-N-(4-trifluoromethylpiperid-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine.
The present invention provides a process for the preparation of a compound of formula I, which comprises
(a) treating a 5,7-dihalo-triazolopyrimidine of formula II,
in which
L
1
through L
5
and Hal are as defined in any one of the preceding claims; and
with an amine of the general formula III
in which
R
1
and R
2
are as defined
Albert Guido
Pees Klaus-Juergen
Rehnig Annerose
BASF - Aktiengesellschaft
Costello Charles F.
Ford John M.
LandOfFree
Fungicidal fluoro-substituted... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fungicidal fluoro-substituted..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fungicidal fluoro-substituted... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2902598