Phenyl-substituted cyclic enaminones

Details Phenyl-substituted cyclic enaminones Phenyl-substituted cyclic enaminones

2001-07-16

2002-09-24

Chang, Ceila (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S130000, C540S610000, C546S238000, C548S566000

Reexamination Certificate

active

06455472

ABSTRACT:

This application is a 35 U.S.C. 371 application of PCT application Ser. No. PCT/EP99/08366, filed on Nov. 2, 1999, which in turn claimed priority on German application 198 51 986.9, filed on Nov. 11, 1998.
FIELD OF THE INVENTION
The invention relates to novel phenyl-substituted cyclic enaminones, to a plurality of processes for their preparation, to intermediates and to the use of the enaminones as crop protection agents, in particular as herbicides, acaricides, nematicides and insecticides.
BACKGROUND OF THE INVENTION
Certain cyclic enaminones which are substituted in the phenyl ring have already been disclosed as intermediates for antibacterial quinolones (R. G. Glushkov, N. B. Marchenko, A. N. Padeiskaya, L. D. Shipilova, Pharmn. Chem. J. (Engl. Transl.) 24, 5460-465, (1990)). Furthermore, cyclic enaminones which are not substituted in the phenyl ring have been disclosed (M. V. Mezentseva, A. V. Kadushkin, L. M. Alekseeva, A. S. Sokolova, V. G. Granik, Pharm. Chem. J. (Engl. Transl.) 25, 858-864 (1991); G. M. Coppola, R. Damon, A. D. Kahle, M. J. Shapiro, J. Org. Chem. 46, 1221-1222, (1981); D. Brillon, G. Sauvé, J. Org. Chem. 55, 2246-2249, (1990)). A use of these compounds as crop protection agents has not yet been described.
SUMMARY OF THE INVENTION
Novel cyclic enaminones may be used as crop protection agents.
DETAILED DESCRIPTION
The novel cyclic enaminones are described in a general manner by the formula (I)
in which
K represents oxygen or sulphur,
Ar represents in each case substituted phenyl, naphthyl or represents in each case optionally substituted mono or bicyclic hetaryl having 5 to 10 ring atoms,
X represents CN,
Y represents halogen or in each case optionally substituted alkyl, alkoxy, phenyl, phenylalkyl, hetaryl, hetarylalkyl or represents the groups
two adjacent Y
n
furthermore represent an optionally substituted saturated or unsaturated cycle which may optionally be interrupted by heteroatoms, and
Z represents hydrogen, represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkyl-alkyl, alkoxyalkyl, phenoxyalkyl, phenylalkyl-oxyalkyl, phenylthioalkyl, phenylalkyl-thioalkyl, phenyl, phenylalkyl, hetaryl, hetarylalkyl or represents the groups
 or cyano,
l represents 0 to 3,
m represents 1 to 3,
n represents, depending on m, 0 to 4,
R
1
represents hydrogen, represents in each case optionally substituted, saturated or unsaturated alkyl or cycloalkyl, each of which is optionally interrupted by heteroatoms, represents in each case optionally substituted phenyl or hetaryl, represents in each case optionally substituted phenylalkyl or hetarylalkyl,
R
2
represents hydrogen, represents in each case optionally substituted, saturated or unsaturated alkyl or alkoxy, represents in each case optionally substituted phenyl, phenylalkyl or phenylalkyloxy, or
R
1
, R
2
together with the nitrogen atom to which they are attached may furthermore represent an optionally substituted cycle which is optionally interrupted by heteroatoms,
R
3
represents hydrogen, represents in each case optionally substituted alkyl or alkoxy, represents in each case optionally substituted phenyl or phenylalkyl,
R
4
represents hydrogen or represents optionally substituted alkyl, and
R
5
, R
6
independently of one another represent hydrogen or represent optionally substituted alkyl.
Compounds of the following formula:
are excluded.
For the compounds of the formula (I), the following applies:
Ar preferably represents Ar
1
, where Ar
1
represents phenyl, naphthyl or mono- or bicyclic hetaryl having five to ten ring atoms, each of which radicals is optionally mono to pentasubstituted by halogen, C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkinyl, C
1
-C
8
-alkoxy, C
2
-C
8
-alkenyloxy, C
3
-C
8
-alkinyloxy, C
1
-C
8
-alkylthio, C
1
-C
6
-alkylsulphinyl, C
1
-C
6
-alkylsulphonyl, C
1
-C
6
-halogenoalkyl, C
1
-C
6
-halogenoalkoxy, C
2
-C
8
-halogenoalkenyloxy, C
1
-C
2
-alklidenediyi-dioxy, C
1
-C
2
-halogenoalkylidenediyl-dioxy, halogeno-C
1
-C
4
-alkylthio, halogeno-C
1
-C
4
-alkylsulphinyl, halogeno-C
1
-C
4
-alkylsulphonyl, hydroxyl, mercapto, nitro, cyano, amino, or by the groups
 or represents Ar
2
, where Ar
2
represents Ar
1
which is additionally substituted by phenyl, naphthyl, five- or six-membered hetaryl, phenyl-C
1
-C
4
-alkyl, phenoxy, phenyl-S(O)
g
—, five- or six-membered hetaryloxy or hetaryl-S(O)
g
, where these substituents for their part are in each case optionally mono- to tetrasubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, nitro or cyano.
K preferably represents oxygen or sulphur.
L preferably represents oxygen or sulphur.
X preferably represents CN,
Y preferably represents halogen, C
1
-C
6
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
6
-alkoxy, represents phenyl, phenyl-C
1
-C
4
-alkyl, five- or six-membered hetaryl or five- or six-membered hetaryl-C
1
-C
4
-alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, cyano or nitro, or represents the groups
 Two adjacent Y
n
preferably represent a 5- to 8-membered, saturated or unsaturated cycle which may be interrupted by 1 to 3 heteroatoms from the group consisting of N, O, S and which may optionally be mono- to trisubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, cyano or nitro.
Z preferably represents hydrogen, represents in each case optionally fluorine- and/or chlorine-substituted C
1
-C
8
-alkyl, cyano-C
1
-C
6
-alkyl, C
3
-C
8
-alknyl, C
3
-C
8
-alkinyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
2
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkoxy-C
1
-C
4
-alkyl, represents phenoxy-C
1
-C
4
-alkyl, phenyl-C
1
-C
4
-alkyloxy-C
1
-C
4
-alkyl, phenylthio-C
1
-C
4
-alkyl, phenyl-C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, phenyl, phenyl-C
1
-C
4
-alkyl, five- or six-membered hetaryl, five- or six-membered hetaryl-C
1
-C
4
-alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, nitro or cyano, or represents the groups
 or cyano, where
g preferably represents 0 to 2,
l preferably represents 0 to 2,
R
1
preferably represents hydrogen (but not for the radicals —CO
2
R
1
and —SO
2
R
1
), represents in each case optionally fluorine- and/or chlorine-substituted C
1
-C
10
-alkyl, C
2
-C
10
-alkenyl, C
3
-C
6
-alkinyl, represents in each case optionally fluorine-, chlorine, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy-substituted C
3
-C
8
-cycloalkyl or C
5
-C
8
-cycloalkenyl in which optionally one methylene group may be interrupted by oxygen or sulphur, or represents phenyl, pyridyl, thienyl, pyrimidyl, thiazolyl, phenyl-C
1
-C
4
-alkyl, pyridyl-C
1
-C
2
-alkyl, thiazolyl-C
1
-C
2
-alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, cyano or nitro,
R
2
preferably represents hydrogen, represents in each case optionally fluorine- and/or chlorine-substituted C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkinyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy or represents phenyl, phenyl-C
1
-C
4
-alkyl or phenyl-C
1
-C
4
-alkoxy, each of which is optionally mono- to tetrasubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, cyano or nitro,
R
1
,R
2
together with the nitrogen atom to which they are attached furthermore preferably represent an in each case optionally C
1
-C
4
-alkyl-substituted five to eight-membered cycle in which optionally one methylene group may be replaced by oxygen or sulphur,
R
3
preferably represents hydrogen, optionally halogen-substituted C
1
-C
6
-alkyl or represents phenyl or phenyl-C
1
-C
2
-alkyl each of which is optionally mono- to tetrasubstituted by halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-halogenoalkoxy, cyano or

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