Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-08-04
2001-04-03
Raymond, Richard L. (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S274000, C544S310000, C544S311000, C544S316000, C544S318000, C544S319000, C544S322000, C544S333000, C544S335000
Reexamination Certificate
active
06211190
ABSTRACT:
The present invention relates to pyrimidine derivatives of the formula I
where the substituents have the following meanings:
X is C(CO
2
CH
3
)═NOCH
3
, C(CONHCH
3
)═NOCH
3
, C(CO
2
CH
3
)═CHOCH
3
, C(CO
2
CH
3
)═CHCH
3
, N(CO
2
CH
3
)—OCH
3
;
R
1
and R
2
independently of one another are hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxy;
A is
where the bond marked by * is to Y;
R
3
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, phenoxy-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl, cyano, C
1
-C
4
-alkoxy, hydroxyl, halogen;
R
4
is hydrogen, C
1
-C
8
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
6
-cyanoalkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
2
-C
4
-alkenyloxy-C
1
-C
4
-alkyl, C
1
-C
4
-halo-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-oxoalkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, C
2
-C
4
-haloalkenyl, C
2
-C
4
-haloalkynyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy;
Y is hydrogen, hydroxyl, halogen, unsubstituted or substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio,
where if X is C(CO
2
CH
3
)═CHOCH
3
A is not —O—,
or its salts.
Preferred compounds of the formula I, are those where the substituents have the following meanings:
X is C(CO
2
CH
3
)═NOCH
3
, C(CONHCH
3
)═NOCH
3
, C(CO
2
CH
3
)═CHOCH
3
, C(CO
2
CH
3
)═CHCH
3
, N(CO
2
CH
3
)—OCH
3
;
R
1
and R
2
independently of one another are hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxy;
A is
where the bond marked by * is to Y;
R
3
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, phenoxy-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl, cyano, hydroxyl, halogen;
R
4
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, C
2
-C
4
-haloalkenyl, C
2
-C
4
-haloalkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxy;
Y is unsubstituted or substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, haloalkyl or alkoxy,
where if X is C(CO
2
CH
3
)═CHOCH
3
A is not —O—,
and their salts.
Especially preferred compounds of the formula 1 as claimed in claim
1
are those where the substituent Y has the following meanings:
hydrogen, hydroxyl, halogen, C
1
-C
4
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-alkynyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyloxy, C
1
-C
4
-alkylthio, C
3
-C
6
-cycloalkyl, C
5
-C
8
-cycoalkenyl, heterocyclyl, aryl, aryloxy, arylthio, aryl-C
1
-C
4
-alkyl, aryl-C
2
-C
4
-alkenyl, aryloxy-C
1
-C
4
-alkyl, aryl-C
1
-C
4
-alkoxy, hetaryl, hetaryloxy, hetarylthio, hetaryl-C
1
-C
4
-alkyl, hetarylthio-C
1
-C
4
-alkyl, hetaryl-C
1
-C
4
-alkoxy or hetaryl-C
2
-C
4
-alkenyl, where the cyclic radicals can be partially or completely halogenated and/or can carry 1 to 3 of the following groups:
cyano, nitro, hydroxyl, mercapto, amino, formyl, carboxyl, aminocarbonyl, aminothiocarbonyl,
C
1
-C
12
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-hydroxyalkyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylcarbonyloxy, C
1
-C
6
-alkoxycarbonyl, benzyloxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, C(═NOR
b
)—Z
n
—R
c
, NR
f
—CO—D—R
9
, benzyl, benzyloxy, aryl, aryloxy, hetaryl or hetaryloxy, where the 6 last mentioned radicals can be partially or completely halogenated and/or can carry 1 to 3 of the following groups: cyano, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-carbonyl, C
1
-C
4
-alkoxy, nitro, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-haloalkyl, hydroxy, rhodano, formyl, aminocarbonylamino, methylsulfonylamino, aminocarbonyl, C
1
-C
6
-alkylaminocarbonyl;
Z is oxygen, sulfur or nitrogen, the nitrogen bearing hydrogen or C
1
-C
6
-alkyl;
D is a direct bond, oxygen or NR
h
;
n is 0 or 1;
R
b
and R
c
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl or benzyl;
R
f
is hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl;
R
g
and R
h
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl , C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, aryl, aryl-C
1
-C
6
-alkyl, hetaryl or hetaryl-C
1
-C
6
-alkyl,
R
9
hydrogen or C
1
-C
6
-alkyl.
Particulary preferred compounds are those where the substituent Y has the following meanings:
C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
3
-C
6
-cycloalkyl, C
5
-C
8
-cycoalkenyl, heterocyclyl, aryl or hetaryl, where the cyclic radicals can be partially or completely halogenated and/or can carry 1 to 3 of the following groups:
cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,
C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylsulfoxyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkoxy, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylaminocarbonyl, di-C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-alkylaminothiocarbonyl, di-C
1
-C
6
-alkylaminothiocarbonyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy, C(═NOR
b
)—Z
n
—R
c
or NR
f
—CO—D—R
9
;
Z is oxygen, sulfur or nitrogen, the nitrogen bearing hydrogen or C
1
-C
6
-alkyl;
D is a direct bond, oxygen or NR
h
;
n is 0 or 1;
R
b
and R
c
independently of one another are hydrogen or C
1
-C
6
-alkyl;
R
f
is hydrogen, hydroxyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl;
R
g
and R
h
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, aryl, aryl-C
1
-C
6
-alkyl, hetaryl or hetaryl-C
1
-C
6
-alkyl.
The invention additionally relates to processes and intermediates for preparing these compounds and to compositions comprising them for controlling animal pests and harmful fungi.
Phenylacetic acid derivatives for controlling pests are disclosed in the literature (EP-A 422 597; EP-A 463 488; EP-A 370 629; EP-A 460 575; EP-A 472 300; WO-A 90/07,493; WO-A 92/13,830; WO-A 92/18,487; WO-A 95/18,789; WO-A 95/21,153; WO-A 95/21,154; WO-A 95/21,156).
Pyrimidine derivatives for controlling pests are furthermore disclosed in the literature (EP-A 634 405).
It is an object of the present invention to provide novel compounds having an improved action.
We have found that this object is achieved by the pyrimidine derivatives I defined at the outset. We have additionally found processes and intermediates for their preparation and compositions comprising them for controlling animal pests and harmful fungi, and their use in this context.
The compounds I are obtainable in various ways by methods known per se in the literature.
Fundamentally, it is insignificant in the synthesis of the compounds whether the group X or the group Y—A— is synthesized first.
The synthesis of the group X is disclosed, for example, in the literature cited at the outset and in EP-A 178 826, EP-A 493 711, EP-A 534 216, EP-A 658 541, EP-A 658 542 and EP-A 658 543.
The novel pyrimidines of the formula I, where X is C(CO
2
CH
3
)═NOCH
3
or C(CONHCH
3
)═N—OCH
3
, are thus obtained, for example, by reacting an &agr;-oxopyrimidinylacetic acid derivative of the formula IIa
where Y, A, R
1
and R
2
have the meanings indicated above, in a manner known per se (EP-A-49
Ammermann Eberhard
Bayer Herbert
Grammenos Wassilios
Grote Thomas
Harries Volker
BASF - Aktiengesellschaft
Keil & Weinkauf
Raymond Richard L.
LandOfFree
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