Tetrahydropyrimidine derivatives

Details Tetrahydropyrimidine derivatives Tetrahydropyrimidine derivatives

1998-08-28

2001-01-23

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S112000, C546S113000

Reexamination Certificate

active

06177431

ABSTRACT:

The present invention relates to novel tetrahydropyrimidine derivatives, processes for their preparation and their use for controlling animal pests.
It is already known that certain bicyclic pyrimidine derivatives, such as, in particular, 6-substituted 6,7-dihydro-8-nitro-(5H)-1-(2-chloropyridin-5-yl-methyl or 2-chloro-1,3-thiazol-5-yl-methyl)-imidazolidino-[2,3-f]-pyrimidines, have insecticidal properties (cf. for example EP-A-0 247 477). However, the activity and the spectrum of action of these compounds is, in particular at low application rates and concentrations, not always entirely satisfactory.
This invention, then, provides novel tetrahydropyrimidine derivatives of the formula (I)
in which
A represents one of the groupings (Ia) —(CH
2
)
m
—COXR
1
or
Het represents a five- or six-membered heterocyclic grouping which contains 1, 2, 3 or 4 nitrogen atoms and/or one or two oxygen or sulphur atoms as heteroatom ring members—the number of the ring heteroatoms being 1, 2, 3 or 4—and which is optionally substituted by halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkinyloxy, alkylthio, halogenoalkylthio, alkenylthio, halogenoalkenylthio, alkinylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, amino, alkylamino, dialkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and/or alkoxycarbonyl,
R
1
represents hydrogen, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, optionally substituted aralkyl or optionally substituted 5- or 6-membered heterocyclylalkyl,
R
2
represents optionally substituted alkyl or aralkyl,
X represents oxygen or the groupings —NH— and —N-alkyl-,
m represents integers from 1 to 20 and
n represents integers from 0 to 2,
but excluding compounds of the formula (I) in which simultaneously
A represents the grouping (Ia),
Het represents
R
1
represents hydrogen or ethyl,
X represents oxygen,
m represents 1 or 2 and
n represents 0.
Furthermore, it was found that the tetrahydropyrimidine derivatives of the formula (I) are obtained when
a) nitromethylene derivatives of the formula (II)
in which
Het and n are as defined above
are reacted with amines of the formula (IIIa) or (IIIb)
H
2
N—(CH
2
)
m
—CO—X—R
1
  (IIIa)
in which
R
1
, R
2
, X and m are as defined above,
optionally in the form of their hydrohalides in the presence of at least twice the molar amount of formaldehyde, if appropriate in the presence of an acid catalyst and if appropriate in the presence of a diluent and if appropriate in the presence of a base;
or
b) nitropyrimidine derivatives of the formula (IV)
in which
A and n are as defined above,
are reacted with compounds of the formula (V)
Het—CH
2
—L  (V)
in which
Het is as defined above and
L represents an anionic leaving group,
in the presence of a base and, if appropriate, in the presence of a diluent.
Finally, it has been found that the novel tetrahydropyrimidine derivatives of the formula (I) have pronounced biological properties and are especially suitable for controlling animal pests, in particular insects, arachnids and nematodes encountered in agriculture, in forestry, in the protection of stored products and materials, and in the hygiene sector.
Formula (I) provides a general definition of the tetrahydropyrimidine derivatives according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow will now be illustrated:
Het preferably represents a five- or six-membered grouping from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, C
1
-C
4
-alkyl (which is optionally fluorine- and/or chlorine-substituted), C
2
-C
4
-alkenyl (which is optionally fluorine- and/or chlorine-substituted), C
2
-C
4
-alkinyl, C
1
-C
4
-alkoxy (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkenyloxy (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkinyloxy, C
1
-C
4
-alkylthio (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkenylthio (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkinylthio, C
1
-C
4
-alkylsulphinyl (which is optionally fluorine- and/or chlorine-substituted), C
1
-C
4
-alkylsulphonyl (which is optionally fluorine- and/or chlorine-substituted), amino, C
1
-C
4
-alkylamino, di-(C
1
-C
4
-alkyl)-amino, phenyl, phenoxy, phenylthio, phenylamino, benzyl, formylamino, C
1
-C
4
-alkyl, carbonylamino, formyl, carbamoyl, C
1
-C
4
-alkyl-carbonyl and/or C
1
-C
4
-alkoxy-carbonyl.
R
1
preferably represents hydrogen, C
1
-C
12
-alkyl, C
1
-C
6
-halogenoalkyl, C
2
-C
6
-alkenyl, or C
2
-C
6
-halogenoalkenyl, or phenyl-C
1
-C
4
-alkyl optionally substituted by one to five identical or different substituents, suitable phenyl substituents being:
halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, C
1
-C
4
-halogenoalkylthio, C
1
-C
4
-alkoxycarbonyl, amino, C
1
-C
4
-alkylamino or di-(C
1
-C
4
-alkyl)-amino;
or 5- or 6-membered heterocyclyl-C
1
-C
4
-alkyl optionally substituted by one to three identical or different substituents, the heterocyclic grouping being from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, C
1
-C
4
-alkyl (which is optionally fluorine- and/or chlorine-substituted), C
2
-C
4
-alkenyl (which is optionally fluorine- and/or chlorine-substituted), C
2
-C
4
-alkinyl, C
1
-C
4
-alkoxy (which is optionally fluorine- and/or chlorine-substituted C
3
-C
4
-alkenyloxy (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkinyloxy, C
1
-C
4
-alkylthio (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkenylthio (which is optionally fluorine- and/or chlorine-substituted), C
3
-C
4
-alkinylthio, C
1
-C
4
-alkylsulphinyl (which is optionally fluorine- and/or chlorine-substituted), C
1
-C
4
-alkylsulphonyl (which is optionally fluorine- and/or chlorine-substituted), amino, C
1
-C
4
-alkylamino, di-(C
1
-C
4
-alkyl)-amino, phenyl, phenoxy, phenylthio, phenylamino, benzyl, formylamino, C
1
-C
4
-alkyl, carbonylamino, formyl, carbamoyl, C
1
-C
4
-alkyl-carbonyl and/or C
1
-C
4
-alkoxy-carbonyl.
R
2
preferably represents C
1
-C
8
-alkyl or optionally substituted benzyl,
X preferably represents oxygen or the groupings —NH— and —N—(C
1
-C
8
-alkyl)—.
m preferably represents integers from 1 to 12.
n preferably represents the numbers 0 and 1,
There shall be excluded compounds in which simultaneously
A represents the grouping (Ia),
Het represents
R
1
represents hydrogen or ethyl,
X represents oxygen,
m represents 1 or 2 and
n represents 0.
Het particularly preferably represents a five- or six-membered heterocyclic grouping from the group consisting of pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl, each of which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, iodine, cyano, nitro, C
1
-C
2
-alkyl (which is optionally fluorine- and/or chlorine-substituted), C
1
-C
2
-alkoxy (which is optionally fluorine- and/or chlor

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