Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2003-04-01
2003-12-30
Solola, Taofiq (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06670488
ABSTRACT:
The invention relates to novel phenyl-substituted cyclic ketoenols, to a plurality of processes and intermediates for their preparation and to their use as pesticides and herbicides.
It is already known that certain phenyl-substituted cyclic ketoenols are active as insecticides, acaricides and/or herbicides.
1H-Arylpyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, DE-44 40 594, DE-196 49 665, WO 94/01 997, WO 95/01 358, WO 95/20 572, EP-A-668 267, WO 95/26 954, WO 96/25395, WO 96/35 664, WO 97/01 535 and WO 97/02 243) and their use as pesticides and, of some of them, as herbicides, are known.
However, the herbicidal, acaricidal and insecticidal activity and/or spectrum of activity and/or plant safety of these compounds, in particular with respect to crop plants, is not always satisfactory.
This invention, accordingly, provides novel compounds of the formula (I)
in which
W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy or represents phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, each of which is optionally substituted,
X represents halogen, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, cyano, nitro or represents phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, each of which is optionally substituted,
Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro,
Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or represents phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, each of which is optionally substituted,
A represents alkyl or optionally substituted phenyl,
B represents hydrogen or alkyl,
G represents hydrogen (a) or one of the radicals
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 alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, each of which is optionally substituted by halogen or cyano, or represents cycloalkyl or heterocyclyl, each of which is optionally substituted by halogen, alkyl or alkoxy, or represents phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, each of which is optionally substituted,
R
2
represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each of which is optionally substituted by halogen or cyano, or represents cycloalkyl, phenyl or benzyl, each of which is optionally substituted,
R
3
, R
4
and R
5
independently of one another each represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, each of which is optionally substituted by halogen, or represent phenyl, benzyl, phenoxl or phenylthio, each of which is optionally substituted,
R
6
and R
7
independently of one another each represent hydrogen, represent alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of which is optionally substituted by halogen or cyano, represent phenyl or benzyl, each of which is optionally substituted, or together with the linking N atom form a cycle which optionally contains oxygen or sulphur and which is optionally substituted.
The compounds of the formula (I) can be present, depending, inter alia, on the nature of the substituents, as optical isomers or isomer mixtures of differing composition which, if appropriate, can be separated in a customary manner. Both the pure isomers and the isomer mxtures, their preparation and use, and compositions comprising them are part of the subject matter of the present invention. In the following, for simplicity, however, compounds of the formula (I) are always referred to, although both pure compounds and, if appropriate, mixtures having different proportions of isomeric compounds are intended.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-a) to (I-g) result:
in which
A, B, E, L, M, W, X, Y, Z, 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) compounds of the formula (I-a)
in which
A, B, W, X, Y and Z are each as defined above,
are obtained when
compounds of the formula (II)
in which
A, B, W, X, Y and Z are each as defined above,
and
R
8
represents alkyl (preferably C
1
-C
6
-alkyl),
are intramolecularly condensed in the presence of a diluent and in the presence of a base.
Furthermore, it has been found
(B) that the compounds of the formula (I-b) shown above in which R
1
, A, B, W, X, Y and Z are each as defined above are obtained when compounds of the formula (I-a) shown above in which A, B, W, X, Y and Z are each as defined above,
&agr;) are reacted with acyl halides of the formula (III)
in which
R
1
is as defined above and
Hal represents halogen (in particular chlorine or bromine)
or
&bgr;) are reacted with carboxylic anhydrides of the formula (IV)
R
1
—CO—O—CO—R
1
(IV)
in which
R
1
is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
(C) that the compounds of the formula (I-c) shown above in which R
2
, A, B, W, M, X, Y and Z are each as defined above and L represents oxygen are obtained when compounds of the formula (I-a) shown above in which A, B, W, X, Y and Z are each as defined above,
are reacted with chloroformic esters or chioroformic thioesters of the formula (V)
R
2
—M—CO—Cl (V)
in which
R
2
and M are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
(D) that compounds of the formula (I-c) shown above in which R
2
A, B, W, M, X, Y and Z are each as defined above and L represents sulphur are obtained when compounds of the formula (I-a) shown above in which A, B, W, X, Y and Z are each as defined above,
are reacted with chloromonothioformic esters or chlorodithioformic esters of the formula (VI)
in which
M and R
2
are each as defined above,
if appropriate in t he presence of a diluent and if appropriate in the presence of an acid binder;
(E) that compounds of the formula (I-d) shown above in which R
3
, A, B, W, X, Y and Z are each as defined above are obtained when compounds of the formula (I-a) shown above in which A, B, W, X, Y and Z are each as defined above,
are reacted with sulphonyl chlorides of the formula (VII)
R
3
—SO
2
—Cl (VII)
in which
R
3
is as defined above,
if appropriate in t he presence of a diluent and if appropriate in the presence of an acid binder,
(F) that compounds of the formula (I-e) shown above in which L, R
4
, R
5
, A, B, W, X, Y and Z are each as defined above are obtained when compounds of the formula (I-a) shown above in which A, B, W, X, Y and Z are each as defined above,
are reacted with phosphorus compounds of the formula (VIII)
in which
L, R
4
and R
5
are each as defined above and
Hal represents halogen (in particular chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder;
(G) that compounds of the formula (I-f) shown above in which E, A, B, W, X, Y and Z are each as defined above are obtained when compounds of the formula (I-a) in which A, B, W, X, Y and Z are each as defined above,
are reacted with metal compounds or amines of the formulae (IX) or (X)
Me(OR
9
)
t
(IX)
in which
Me represents a mono- or divalent metal (preferably an alkali metal or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
t represents the number 1 or 2 and
R
9
, R
10
, R
11
independently of one another each represent hydrogen or alkyl (preferably C
1
-C
8
-alkyl),
if appropriate in the presence of a diluent;
(H) that compounds of the formula (I-g) shown above in which L, R
6
, R
7
, A, B, W, X, Y and Z are each as defined above
Andersch Wolfram
Erdelen Christoph
Fischer Reiner
Hagemann Hermann
Schneider Udo
Bayer Aktiengesellschaft
Harmuth Raymond J.
Henderson Richard E.L.
Solola Taofiq
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