Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-06-12
2004-06-08
Berch, Mark L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S263000, C544S229000
Reexamination Certificate
active
06747033
ABSTRACT:
The present invention provides compounds of formula I
in which
R
1
is C
1
-C
10
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
3
-C
8
-cycloal-kyl-C
1
-C
6
-alkyl, C
2
-C
10
-alkenyl, C
2
-C
10
-alkynyl, C
4
-C
10
-alka-dienyl, C
1
-C
10
-haloalkyl, trihydrocarbylsilyl, formyl, C
1
-C
10
-alkanoyl or C
1
-C
10
-alkoxycarbonyl group being attached either to the nitrogen in the 3- or 4-position;
R
2
is hydrogen, C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl, C
2
-C
10
-alkynyl, C
4
-C
10
-alkadienyl, C
1
-C
10
-haloalkyl, C
3
-C
6
-cycloalkyl, C
8
-C
14
-bicycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl or heterocyclic groups containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members;
R
3
is phenyl, C
3
-C
6
-cycloalkyl or 5- or 6-membered heteroaryl containing besides carbon atoms one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members;
R
4
is halogen, amino, C
1
-C
10
-alkoxy, C
l
-C
10
-haloalkoxy, C
1
-C
10
-alkylamino or di-C
1
-C
10
-alkylamino;
wherein the bent line indicates that the double Bond may be located between the 3- and 9-position or the 4- and 9-Position; and the zigzag line
indicates that the groups connected may have the (E)- or (Z)-configuration;
R
1
to R
4
groups independently from one another may be unsubstituted or substituted by one to three groups R
a
:
R
a
halogen, nitro, cyano, hydroxy, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-halocycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, tri-C
1
-C
4
-alkylsilyl, phenyl, halo- or dihalo-phenyl or pyridyl;
It is an object of the present invention to provide fungicidal active compounds.
Moreover, the invention relates to processes for preparing these compounds, to compositions comprising them and to their use for controlling harmful fungi.
Fungicidal 7-amino-triazolopyrimidines are disclosed for example by U.S. Pat. No. 5,593,996, WO-A 98/14608, FR-A 2,765,875 and WO-A 99/48893.
It is an object of the present invention to provide compounds having improved activity.
We have found that this object is achieved by the compounds defined at the outset. Furthermore, we have found processes for their preparation, compositions comprising them and methods for controlling animal pests and harmful fungi using the compounds I.
The present invention further provides a process for the preparation of a compound of formula I as defined above which comprises treating a compound of formula II:
in which R
2
through R
4
are as defined in claim 1;
with an alkylation agent of formula III:
R
1
—X III
in which R
1
is as defined in formula I and X represents a nucleophilic exchangeable leaving group, preferably a halogen atom, in particular a bromine or iodine atom, in the presence of a weak base or a buffer system.
Compounds of formula II are known for example from U.S. Pat. No. 5,593,996, WO 98/14608, FR-A 2,765,875 or WO-A 99/48893.
The reaction between the triazolopyrimidines of formula II, the weak base and the alkylating agent of formula III is preferably carried out in the presence of an inert solvent. Suitable solvents include ethers, such as dioxane, diethyl ether and tetrahydrofuran, halogenated hydrocarbons such as dichioromethane, amides, such as dimethylformamide or N-methylpyrrolidone and aromatic hydrocarbons, for example toluene or mixtures of these solvents.
The reaction is suitably carried out at a temperature in the range from −78° C. to 100° C., the preferred reaction temperature is from 10° C. to 80° C., particular at ambient temperature. Suitable weak bases include tertiary amines such as triethylamine or pyridine, metal carbonates such as sodium carbonate or carbonate or metal hydrogencarbonates such as sodium hydrogencarbonate or potassium hydrogencarbonate.
In the symbol definitions given in the formulae above, collective terms were used which generally represent the following substituents:
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 fluorine or chlorine atom.
The terms alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl as used herein with respect to a radical or moiety refer to a straight or branched chain radical or moiety. 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 4 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. Suitably a haloalkyl moiety has from 1 to 6 fluorine atoms. A preferred haloalkyl moiety is the 2,2,2-trifluoroethyl or 1,1,1-trifluoroprop-2-yl group.
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 sulfur, at least one of which being nitrogen, oxygen or sulfur, in particular pyridyl, pyrimidyl, pyrazolyl or thienyl.
The term cycloalkyl, as used herein which 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 cyclopentyl being optionally substituted by one or more halogen atoms, nitro, cyano, alkyl, preferably C
1
-C
6
-alkyl, alkoxy, preferably C
1
-C
6
-alkoxy.
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 sulfur, at least one of which being-nitrogen, oxygen or sulfur being optionally substituted by one or more halogen atoms, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, in particular pyrrolodinyl, pyrazolidinyl, piperidinyl, piperazinyl or morpholin-4-yl.
The term trihydrocarbylsilyl, as used herein which respect to a radical or moiety refers to a silyl group which is substituted by three alkyl and/or phenyl groups. Most preferred are trimethylsilyl, triethylsityl, tert.-butyldimethylsilyl and tert.-butyl-di-phenylsilyl.
The invention especially relates to compounds of formula I in which any alkyl or haloalkyl part of the groups R
1
, R
2
, R
3
or R
4
, which may be straight chained or branched, contains preferably 1 to 9 carbon atoms, mores preferably 2 to 6 carbon atoms, any alkenyl, alkadienyl or alkynyl part of the substituents R
1
or R
2
contains preferably 2 to 9 carbon atoms, more preferably 3 to 6 carbon atoms, any cycloalkyl part of the substituent R
1
contains preferably from 3 to 8 a carbon atoms, more preferably from 3 to 6 carbon atoms. Any alkyl, alkenyl, alkadienyl or alkynyl group may be linear or branched. A 5- to 6-membered heterocyclic group may be any heterocyclic group with 5 to 6 ring atoms, interrupted by one or mores heteroatoms selected from sulfur, nitrogen, and oxygen, preferably oxygen.
The invention especially relates to compounds of the general formula I in which R
1
represents a straight-chained or branched C
1
-C
10
-alkyl, in particular a straight-chained C
1
-C
6
-alkyl group, a C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl, C
1
-C
10
-alkoxy-C
1
-C
6
-alkyl or a C
1
-C
10
-haloalkyl group.
The invention especially relates to compounds of the general formula I in which R
2
represents a straight-chained or branched C
1
-C
10
-alkyl, in particular a branched C
3
-C
6
-alkyl group, a C
3
-C
8
-cycloalkyl, a C
3
-C
8
-cycloalkyl-C
1
-C
6
-alkyl, C
1
-C
10
-alkoxy-C
1
-C
6
-alkyl, a C
1
-C
10
-haloalkyl or a phenyl group being optionally substituted by one to three halogen atoms or C
1
-C
10
-alkyl or C
1
-C
10
-alkoxy groups.
Included in the scope of the present invention are (R) and (S) isomers of compounds of general formula I having a chiral center and the racemates thereof, and salts, N-oxides and acid addition compounds.
With respect to their intended use, preference is given to compounds of formula I having the following substituents, where the preference is valid in each case on its o
BASF - Aktiengesellschaft
Berch Mark L.
Keil & Weinkauf
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