Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-02-01
2001-03-13
Powers, Fiona T. (Department: 1626)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S283000, C514S237200, C514S409000, C544S141000, C548S410000, C549S333000, C549S334000, C549S371000
Reexamination Certificate
active
06200932
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel phenyl-substituted cyclic ketoenols, to a plurality of processes for their preparation and to their use as pesticides and herbicides.
BACKGROUND OF THE INVENTION
1H-arylpyrrolidine-dione derivatives (EP-456 063, EP-521 334, EP-596 298, EP-613 884, EP-613 885, WO 94/01 997, WO 95/01358, WO 95/26954, WO 96/00382,
WO 95/20572, EP 668 267) having herbicidal, acaricidal and insecticidal action are known.
However, the activity and the activity spectrum of these compounds is, in particular at low application rates and concentrations, not always entirely satisfactory. Furthermore, the crop safety of these compounds is not always sufficient.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel compounds of the formula
in which
X represents halogen, alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkenyloxy, nitro, cyano or represents phenyl, phenoxy, phenylthio, benzyloxy or benzylthio, each of which is optionally substituted,
Y represents hydrogen, halogen alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkenyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,
Z represents halogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, alkoxy, alkenyloxy, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,
n represents 0, 1, 2 or 3,
A represents hydrogen, represents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which is optionally substituted by halogen, represents saturated or unsaturated cycloalkyl which is optionally substituted and in which optionally at least one ring atom is replaced by a heteroatom, or represents aryl, arylalkyl or hetaryl, each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cyano or nitro and which may optionally be substituted by substituted phenoxy, benzyloxy or hetaryloxy,
B represents hydrogen or represents alkyl or alkoxyalkyl, each of which is optionally substituted by halogen, or
A and B together with the linking carbon atom represent a saturated or unsaturated, unsubstituted or substituted ring which optionally contains a 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 alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, each of which is optionally substituted by halogen, or represents optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom 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 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, phenoxy or phenylthio, each of which is optionally substituted, and
R
6
and R
7
independently of one another each represent hydrogen, represent alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which is optionally substituted by halogen, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the linking N atom represent an optionally by oxygen- or sulphur-containing ring.
Depending, inter alia, on the nature of the substituents, the compounds of the formula (I) can be present as geometric and/or optical isomers or isomer mixtures of different -composition which can be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and compositions comprising them form 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.
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-phenylpyrrolidine-2,4-diones or enols thereof of the formula (I-a)
in which
A, B, X, Y, Z and n are each as defined above
are obtained when
N-acylamino acid esters of the formula (II)
in which
A, B, X, Y, Z and n 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.
Furthermore, it has been found
(B)&agr;) that compounds of the formula (I-b) shown above in which A, B, X, Y, Z, R
1
and n are each as defined above are obtained when compounds of the formula (I-a) in which A, B, X, Y, Z and n are each as defined above 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 are reacted
&bgr;) 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 formulae (I-c) shown above in which A, B, R
2
, M, X, Y, Z and n are each as defined above and L represents oxygen are obtained when compounds of the formula (I-a) shown above in which A, B, X, Y, Z and n are each as defined above are in each case
reacted with chloroformic esters or chloroformic thiol esters 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 formulae (I-c) shown above in which A, B, R
2
, M, X, Y, Z and n are each as defined above and L represents sulphur are obtained when compounds of the formula (I-a) shown above in which A, B, X, Y, Z and n are each as defined above are in each case 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 the 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 A, B, R
3
, X, Y, Z and n are each as defined above are obtained when compounds of the formulae (I-a) shown above in which A, B, X, Y, Z and n are each as defined above are in each case
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 the presence of a diluent and if appropriate in the presence of an acid binder,
(F) that compounds of the formulae (I-e) shown above in which A, B, L, R
4
, R
5
, X, Y, Z and n are each as defined above are obtained when compounds of the formulae (I-a) shown above in which A, B, X, Y, Z and n are each as defined above are in each case
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 formulae (I-f) shown above in which A, B, E, X, Y, Z and n are each as defined above are obtained when compounds of the formulae (I-a) in which A, B, X, Y, Z and n are each as defined above are in each case
reacted with metal compounds or amines of the formulae (IX) or (X)
Me(OR
10
)
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
10
, R
11
, R
12
Dahmen Peter
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Schneider Udo
Bayer Aktiengesellschaft
Gil Joseph C.
Powers Fiona T.
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