Substituted pyrimidines, processes for their preparation,...

Details Substituted pyrimidines, processes for their preparation,... Substituted pyrimidines, processes for their preparation,...

1996-03-15

2003-07-22

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...

C514S256000, C514S063000, C514S259500, C514S249000, C544S298000, C544S319000, C544S326000, C544S327000, C544S229000, C544S296000, C544S276000, C544S283000, C544S284000, C544S287000, C544S289000, C544S295000, C544S293000, C544S328000

Reexamination Certificate

active

06596727

ABSTRACT:

The invention relates to novel substituted 4-amino- and 4-alkoxypyrimidines, to processes for their preparation and to their use as pesticides, in particular as insecticides, acaricides and fungicides.
It has already been disclosed that certain substituted 4-aminopyrimidines have a good fungicidal, acaricidal and insecticidal activity (cf. EP-A-57,440, EP-A-196,524, EP-A-264,217, EP-A-276,406, EP-A-323,757, EP-A-326,328, EP-A-326,329, EP-A-326,330, EP-A-356,158, EP-A-370,704, EP-A-411,634, EP-A-424,125, EP-A-452,002, EP-A-459,611, EP-A-447,891). However, the biological activity of these compounds is not satisfactory in all fields of application, in particular when low dosage rates and concentrations are used.
Novel substituted 4-amino- and 4-alkoxypyrimidines of the formula I have been found,
in which
R
1
is hydrogen, halogen, (C
1
-C
4
)-alkyl or (C
3
-C
6
)-cycloalkyl,
R
2
is hydrogen, (C
1
-C
4
)-alkyl, halogen (C
1
-C
4
)-halo-alkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylthio, (C
1
-C
4
)-alkylthio-(C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkylamino or di-(C
1
-C
4
)-alkylamino,
R
3
is hydrogen, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy, halogen, (C
1
-C
4
)-alkylthio, amino, (C
1
-C
4
)-alkylamino or di-(C
1
-C
4
)-alkylamino or
R
2
and R
3
together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered isocyclic ring which, if it is a 5-membered ring, can contain an oxygen or sulfur atom in place of CH
2
and which is optionally substituted by 1, 2 or 3 identical or different radicals, these radicals being (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-halo-alkyl, preferably trifluoromethyl, (C
1
-C
4
)-halo-alkoxy and/or halogen, or
R
2
and R
3
together with the carbon atoms to which they are bonded form a saturated 5-, 6- or 7-membered isocyclic ring which can contain an oxygen or sulfur atom in place of CH
2
and which is optionally substituted by 1, 2 or 3 (C
1
-C
4
)-alkyl groups,
X is NH or oxygen,
E is a direct bond or a straight-chain or branched (C
1
-C
4
)-alkanediyl group, preferably a direct bond,
Q has the meaning Q
1
and
Q
1
is a cycloalkyl group of the formula II
 in which n is an integer from 2 to 7,
R
4
and R
5
are identical or different and are in each case hydrogen, (C
1
-C
12
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
3
-C
8
)-cyclo alkyl-(C
1
-C
4
)-alkyl, (C
1
-C
8
)-alkoxy, (C
3
-C
8
)-cyclo-alkoxy, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkyl, (C
3
-C
8
)-cyclo-alkyl-(C
1
-C
4
)-alkoxy, tri-(C
1
-C
8
)-alkylsilyl, preferably dimethyl-(C
1
-C
8
)-alkylsilyl or tri-ehtylsilyl, di-(C
1
-C
8
)-alkyl-(C
3
-C
8
)-cycloalkyl-silyl, preferably dimethylcyclohexylsilyl, di-(C
1
-C
8
)-alkyl (phenyl-(C
1
-C
4
)-alkyl)-silyl, preferably dimethyl-(phenyl-(C
1
-C
4
)-alkyl)silyl, di-(C
1
-C
8
)-alkyl-(C
1
-C
4
)-haloalkylsilyl, preferably dimethyl-(C
1
-C
4
)-haloalkylsilyl, dimethylphenyl-silyl, (C
1
-C
4
)-haloalkyl, halogen, (C
1
-C
4
)-haloalkoxy, heteroaryl, phenyl, phenyl-(C
1
-C
4
)-alkyl, benzyloxy, benxzyloxy-(C
1
-C
4
)-alkyl, benzylthio, phenylthio or phenoxy, it being possible for the phenyl rings in the seven last-mentioned radicals to be unsubstituted or provided with one or two substituents and these substituents are identical or different and can be in each case (C
1
-C
8
)-alkyl, (C
3
-C
8
)-cycloalkyl, (C
1
-C
4
)-haloalkyl, preferably trifluoromethyl, halogen, (C
1
-C
4
)-dialkylamino, (C
1
-C
4
)-alkylthio, (C
1
-C
8
)-alkoxy, (C
1
-C
4
)-haloalkoxy, (C
1
-C
4
)-alkoxy-(C
1
-C
4
)-alkoxy, H
5
C
2
-O-[CH
2
-CH
2
-O-]
x
, 2-(tetrahydro-2H-pyran-2-yloxy)-ethoxy, (C
2
-C
8
)-alkenyl, (C
2
-C
8
)-alkynyl, benzyloxy which in the phenyl radical optionally carries one or two identical or different substituents selected from the group comprising (C
1
-C
4
)-alkyl, (C
1
-C
4
)-haloalkyl, (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-haloalkoxy and halogen, or tri-(C
1
-C
4
)-alkylsilylmethoxy, preferably dimethyl-(C
1
-C
4
)-alkylsilylmethoxy, (C
3
-C
8
)-cycloalkyl-(C
1
-C
4
)-alkoxy, 1,3-dioxolan-2-ylmethoxy, tetrahydro-furan-2-ylmethoxy or tetrahydro-2H-pyran-2-ylmethoxy, where, both, R
4
and R
5
do not coincidentally denote hydrogen, and where, in two adjacent substituents which are identical or different and are selected from the group comprising (C
1
-C
8
)-alkyl and (C
1
-C
8
)-alkoxy, in each case one hydrogen atom can be replaced by a joint carbon-carbon bond which links these two substituents, or
R
4
and R
5
together with the cycloalkyl group form a 3-8-membered spirocyclic, preferably saturated spirocyclic, ring system which can contain oxygen or sulfur in place of one or two CH
2
groups or
R
4
and R
5
together with the carbon atoms carrying them form a fused 5- or 6-membered, preferably saturated isocycle, in particular a cyclopentane or cyclohexane system,
X is 2, 3 or 4, preferably 2, or
Q has the meaning Q
2
and
Q
2
is a group of the formula III
in which
R
6
is a group of the formula Z-W and Z is a direct bond or carbonyl or sulfonyl and W is an aryl or heteroaryl group which can be unsubstituted or provided with one or two substituents and these substituents are identical or different and are in each case (C
1
-C
8
)-alkyl, (C
3
-C
8
)-cycloalkyl, trifluoromethyl, halogen (C
1
-C
4
)-alkoxy, (C
1
-C
4
)-dialkylamino or (C
1
-C
4
)-alkylthio.
If Q has the meaning Q
1
, R
2
and R
3
together with the carbon atoms carrying them form an unsaturated 6-membered isocyclic ring and R
4
and R
5
form a fused 5- or 6-membered ring, then the meaning 5-membered ring is preferred for the two last-mentioned radicals.
If Q has meaning Q
1
, and R
2
and R
3
together with the carbon atoms carrying them form a furan or thiophene system, then Q
1
is preferably not (C
3
-C
8
)-cycloalkyl which is optionally substituted and the substituents are in particular alkyl such as (C
1
-C
4
)-alkyl, alkoxy such as (C
1
-C
4
)-alkoxy, haloalkyl such as (C
1
-C
4
)-haloalkyl, haloalkoxy such as (C
1
-C
4
)-haloalkoxy or halogen.
Preferred compounds of the formula I are those in which
R
1
is hydrogen, methyl or cyclopropyl,
R
2
is (C
1
-C
4
)-alkyl, chlorine, methoxy, ethoxy or methoxymethyl,
R
3
is hydrogen, (C
1
-C
3
)-alkyl, methoxy, ethoxy or halogen or
R
2
and R
3
together with the carbon atoms to which they are bonded form an unsaturated 5- or 6-membered ring which can contain an oxygen or sulfur atom, or R
2
and R
3
together with the carbon atoms to which they are bonded form a saturated 5- or 6-membered ring which can contain a sulfur atom,
Q has the meaning Q
1
or Q
2
, in particular those compounds of the formula I in which
R
1
is hydrogen or methyl,
R
2
is methyl, ethyl, methoxy, ethoxy or methoxy-methyl,
R
3
is methyl, ethyl, methoxy, chlorine or bromine, or
R
2
and R
3
together with the carbon atoms to which they are bonded form the quinazoline system, or
R
2
and R
3
together with the carbon atoms to which they are bonded form a saturated 6-membered ring which can contain a sulfur atom and
Q has the meaning Q
1
or Q
2
, preferably those compounds of the formula I in which
E is a direct bond,
R
1
is hydrogen,
R
2
is methyl, ethyl or methoxymethyl,
R
3
is chlorine, bromine or methoxy or
R
2
and R
3
together with the carbon atoms to which they are bonded form the quinazoline system which can be substituted by fluorine, chlorine, bromine or methyl, or
R
2
and R
3
together with the pyrimidine ring form the 5,6,7,8-tetrahydroquinazoline system or the 5,6-dihydro-7H-thiopyrano[2,3-d]pyrimidine or the 5,6-dihydro-8H-thiopyrano[3,4-d]pyrimidine system
 and
Q has the meaning Q
1
or Q
2
.
Very particularly preferred compounds of the formula I are those in which
E is a direct bond,
R
1
is hydrogen,
R
2
is methoxymethyl and R
3
is methoxy or
R
2
is methyl or ethyl and R
3
is chlorine or bromine or
R
2
and R
3
together with the carbon atom to which they are bonded form a quinazoline system which is substituted by fluorine, chlorine or methyl, or form a 5,6,7,8-tetrahydroquinazoline system and
Q

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