Heteroaryl-substituted heterocycles

Details Heteroaryl-substituted heterocycles Heteroaryl-substituted heterocycles

2002-12-10

2004-07-27

Chang, Ceila (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S269000, C546S269700, C548S147000, C548S214000

Reexamination Certificate

active

06767864

ABSTRACT:

The present invention relates to novel hetaryl-substituted heterocycles, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
4-Thiazolyl-3-hydroxy-3-pyrroline-2,5-diones are known as glycolic acid oxidase inhibitors; U.S. Pat. No. 4,296,237; U.S. Pat. No. 4,377,588; EP-A-025 232; Rooney C. S. et al., J. Med. Chem. 26 700-714 (1983); Guzel Y. et al. THEOCHEM 366 131-137 (1996).
The present invention provides novel compounds of the formula (I)
in which
W represents N—D
(1)
, oxygen
(2)
or sulphur
(3)
,
Het represents in each case optionally substituted thiazolyl, oxazolyl or pyrazolyl,
A represents hydrogen, in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom, or in each case optionally halogen-, alkyl-, halogenoalkyl, alkoxy-, halogenoalkoxy-, cyano- or nitro-substituted aryl, alarylalkyl or heteroaryl,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated unsubstituted or substituted cycle which optionally contains at least one heteroatom,
D represents hydrogen or represents an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl in which optionally one or more ring members are replaced by heteroatoms, arylalkyl, aryl, heteroarylalkyl or heteroaryl or
A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which is unsubstituted or substituted in the A,D moiety and optionally contains at least one heteroatom,
G represents hydrogen (a) or represents one of the groups
 in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R
1
represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalkyl,
R
2
represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
represents alkyl, halogenoalkyl or represents in each case optionally substituted phenyl or benzyl,
R
4
and R
5
independently of one another each represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another each represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the N atom to which they are attached represent a cycle which is optionally interrupted by oxygen or sulphur.
Depending inter alia on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures in varying composition which may, if desired, be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and use, and compositions comprising them. However, hereinbelow, compounds of the formula (I) are always referred to for the sake of simplicity, although what is meant are both the pure compounds and, if appropriate, also mixtures with varying proportions of isomeric compounds.
Including W=N—D
(1)
, oxygen
(2)
or sulphur
(3)
, the following principal structures (I-1) to (I-3) result:
in which
A, B, D and G are each as defined above and
Het represents thiazolyl or oxazolyl.
Including the various meanings of Het, the following principal structures result:
(I-1-A) to (I-3-B) if W represents N—D
(1)
, oxygen
(2)
or sulphur
(3)
 in which
A, B, D and G are each as defined above and
X represents hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkenyloxy, haloalkenyloxy, nitro, cyano or optionally substituted phenyl,
Y represents halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphoxinyl, alkylsulphonyl or represents in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-1-A-a) to (I-1-A-g) result if W represents N—D
(1)
in which
A, B, D, E, L, M, X, Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-1-B-a) to (J-1-B-g) result if W represents N—D
(1)
in which
A, B, D, E, L, M, X, Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-2-A-a) to (I-2-A-g) result if W represents oxygen
(2)
in which
A, B, E, L, M, X, Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-2-B-a) to (I-2-B-g) result if W represents oxygen
(2)
in which
A, B, E, L, M, X, Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-3-A-a) to (I-3-A-g) result if W represents sulphur
(3)
in which
A, B, E, L, M, X, Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-3-B-a) to (I-3-B-g) result if W represents sulphur
(3)
in which
A, B, E, L, M, X, Y, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Furthermore, it has been found that the novel compounds of the formula (I) are obtained by one of the processes described below:
(A) Substituted 3-hetaryl-pyrrolidine-2,4-diones or enols thereof of the formulae (I-1-A-a) to (I-1-B-a)
 in which
A, B, D and Het are each as defined above
are obtained when N-acylamino acid esters of the formula (II)
 in which
A, B, D and Het are each as defined above
and
R
8
represents alkyl (preferably C
1
-C
6
-alkyl)
are condensed intramolecularly in the presence of a diluent and in the presence of a base.
(B) Moreover, it has been found that substituted 3-heteroaryl-4-hydroxy-&Dgr;
3
-dihydrofuranone derivatives of the formulae (I-2-A-a) to (I-2-B-a)
 in which
A, B and Het are each as defined above
are obtained when carboxylic esters of the formula (III)
 in which
A, B, Het and R
8
are each as defined above
are condensed intramolecularly in the presence of a diluent and in the presence of a base.
(C) Furthermore, it has been found that substituted 3-heteroaryl-4-hydroxy-&Dgr;
3
-dihydrothiophene-2-one derivatives of the formulae (I-3-A-a) to (I-3-B-a)
 in which
A, B and Het are each as defined above
are obtained when &bgr;-ketocarboxylic esters of the formula (IV)
 in which
A, B, Het and R
8
are each as defined above and
W
1
represents hydrogen, halogen, alkyl (preferably C
1
-C
6
-alkyl) or alkoxy (preferably C
1
-C
8
-alkoxy)
are cyclized intramolecularly, if appropriate in the presence of a diluent and in the presence of an acid.
Moreover, it has been found
(D) that the compounds of the formulae (I-1-A-b) to (I-3-B-b) shown above, in which A, B, D, R
1
and Het are each as defined above, are obtained when compounds of the formulae (I-1-A-a) to (I-3-B-a)

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