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
2001-09-04
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...
C540S600000, C544S263000
Reexamination Certificate
active
06284762
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.
U.S. Pat. No. 5,593,996 embraces 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
3
is a trichlorophenyl 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 hyphomycetes class such as
Alternaria solani
and
Botrytis cinerea.
However, there is no single compound disclosed in which R
3
is a 2-halo-4-alkoxyphenyl 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 or heterocyclyl group, or
R
1
and R
2
together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring,
R
3
represents an alkyl, alkenyl, alkynyl, phenylalkyl, alkoxyalkyl, polyalkoxyalkyl, phenyl or haloalkyl group,
L
1
represents a hydrogen, fluorine or chlorine atom,
L
2
represents a fluorine or chlorine atom, and
Hal represents a halogen atom.
The new compounds show excellent fungicidal activity in various crops, against a broad range of phytopathogenic fungi.
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 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
, L
1
, L
2
and Hal have the meaning given above for formula I show excellent fungicidal activity against a broad range of fungi.
As used herein, the term halogen atom may denote a bromine, iodine, chlorine or fluorine atom, and is preferably a bromine, chlorine or fluorine atom, more preferably 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.
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. Suitably, such radicals have up to 10, and preferably 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, 2-methylallyl, 3-methylbut-2-enyl or 2-methylbut-3-enyl group.
Unless otherwise stated herein, the terms alkoxyalkyl, polyalkoxyalkyl as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety having up to 16, in particular up to 10 carbon atoms. Suitably any alkyl moiety of such alkoxyalkyl or polyalkoxyalkyl groups has from 1 to 6 carbon atoms, preferably from 1 to 3 carbon atoms. A preferred alkoxyalkyl moiety is a methoxyalkyl, especially a 2-methoxyethyl or 2-methoxypropyl group. A preferred polyalkoxyalkyl moiety is a dialkoxyalkyl moiety such as 2-methoxyethoxyalkyl or 2-ethoxyethoxyalkyl especially a 2-(2-methoxyethoxy)-ethyl or a 2-(2-ethoxyethoxy)-ethyl group. Suitably an alkenyl moiety has from 2 to 6 carbon atoms. A preferred alkenyl moiety is an allyl, 2-methylallyl, 3-methylbut-2-enyl or 2-methylbut-3-enyl group.
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 optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, and/or alkoxy, preferably C
1-6
alkoxy.
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 is nitrogen, oxygen or sulphur.
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 optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1-6
alkyl, and/or alkoxy, preferably C
1-6
alkoxy.
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 is nitrogen, oxygen or sulphur, optionally substituted by one or more halogen atoms, preferably fluorine, nitro, cyano, alkyl, preferably C
1-6
alkyl, alkoxy, preferably C
1-6
alkoxy, and/or haloalkyl, preferably C
1-6
haloalkyl. Preferred heterocyclyl groups include pyrrolodinyl, pyrrazolidin, piperidinyl, piperazinyl or morpholin-4-yl.
The term haloalkyl as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety having up to 10 carbon and up to 21 halogen atoms, in particular up to 6 carbon and up to 13 halogen atoms. Suitably a haloalkyl moiety of this invention has from 1 to 6 carbon atoms, preferably from 1 to 3 carbon atoms. A preferred haloalkyl moiety is difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,1-trifluoropro-2-yl or pentafluoroethyl group.
The invention especially related to compounds of formula I in which any alkyl part of the groups R
1
, R
2
or R
3
, 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
, R
2
or R
3
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.
The term “optionally substituted” as used herein generally refers to a radical or moiety which is independently 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.
In this invention, a 4- to 6-membered heterocyclic group may be any heterocyclic group with 4 to 6 ring atoms, interrupted by one or more heteroatoms selecte
American Cyanamid Company
Balasubramanian Venkataraman
Maurer Barbara V.
Shah Mukund J.
LandOfFree
Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines 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 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fungicidal 6-(2-halo-4-alkoxyphenyl)-triazolopyrimidines will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2465746