Methods of making substituted phenylketoenols

Details Methods of making substituted phenylketoenols Methods of making substituted phenylketoenols

2002-01-28

2003-10-07

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S060000, C549S265000

Reexamination Certificate

active

06630594

ABSTRACT:

FIELD OF THE INVENTION
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.
BACKGROUND OF THE INVENTION
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 063EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01 997, WO 95/01 358, WO 95/20 572, EP-A-668 267, WO 95/26 954, WO 96/25395 and WO 96/35 664) having insecticidal, acaricidal and in some cases herbicidal activity are known.
It is known that certain substituted &Dgr;
3
-dihydrofuran-2-one-derivatives have herbicidal properties (cf. DE-A-4 014 420). The synthesis of the tetronic acid derivatives (such as, for example, 3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-&Dgr;
3
-dihydrofuran-(2)-one) used as starting materials is also described in DE-A-4 014 420. Compounds of a similar structure are known from the publication Campbell et al., J. Chem. Soc., Perkin Trans. 1, 1985, (8) 1567-76, without an insecticidal and/or acaricidal activity being mentioned. Furthermore, 3aryl-&Dgr;
3
-dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are known from EP-A-528 156, EP-A-0 647 637, WO 96/25395, WO 96/20196 and the abovementioned hitherto undisclosed patent application. 3-aryl-&Dgr;
3
-dihydrothiophene-one derivatives are also known (WO 95/26 345, WO 96/25395 and WO 96/35664).
However, the acaricidal and insecticidal activity and/or spectrum of activity and/or plant tolerance of these compounds, in particular with respect to crop plants, is not always satisfactory.
SUMMARY OF THE INVENTION
The present invention provides methods of making substituted phenylketoenols of the general formula I,
wherein V,W,X,Y,Z and Het are as defined herein.
DETAILED DESCRIPTION OF THE INVENTION
The invention, accordingly, provides novel compounds of the formula (I)
in which
V represents hydrogen, halogen, alkyl or alkoxy,
W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,
X represents halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro or in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,
Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro,
Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or in each case optionally substituted phenoxy, phenylthio, 5- or 6-membered hetaryloxy, 5- or 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or
Y and Z together with the linking carbon atoms represent an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, or
W and Z together with the linking carbon atoms represent an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, or
Het represents one of the groups
 in which
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- or cyano-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or represents in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents in each case optionally halogen- or cyano-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another each represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another each represent hydrogen, represent in each case optionally halogen- or cyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl or represent in each case optionally substituted phenyl or benzyl, or together with the linking N atom form an optionally oxygen- or sulphur-containing and optionally substituted cycle.
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 mixtures, 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 pure compounds and, if appropriate, mixtures having different proportions of isomeric compounds are intended.
Including the meanings (1) to (3) of the group Het, the following principal structures (1-1) to (1-3) result:
in which
G, V, W, X, Y and Z 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-a) to (I-1-g) result if Het represents the group (1)
in which
E, L, M, V, W, X, Y, Z, 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) to (I-2-g) result if Het represents the group (2)
in which
E, L, M, V, W, X, Y, Z, 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), (d), (f) and (g) of the group G, the following principal structures (I-3a) to (I-3-g) result if Het represents the group (3)
in which
E, L, M, V, 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 the processes described below:
(A) compounds of the formula (I-1-a)
 in which
V, W, X, Y and Z are as defined above
are obtained when
compounds of the formula (II)
 in which
V, 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.
(B) Moreover, it has been found that compounds of the formula (I-2-a)
 in which
V, W, X, Y and Z are each as defined above
are obtained when
compounds of the formula (III)
 in which
V, W, X, Y, Z and R
8
are each as defined above
are intramolecularly condensed in the presence of a diluent and in the presence of a base.
(C) Furthermore, it has been found that compounds of the formula (I-3-a)
 in which
V, W, X, Y and Z are each as defined above
are obtained when
compounds of the formula (IV)
 in which
V, W, X, Y, Z and R
8
are each as defined above and
T represents hydrogen, halogen, alkyl (preferably C
1
-C
6
-alkyl) or alkoxy (preferably C
1
-C
8
-alkoxy)
are intramolecularly cyclized, 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-b) to (I-3-b) shown above in which R
1
, V, W, X, Y and Z are each as defined above are obtained when compounds of the formulae (I-1-a) to (I-3-a) shown above in which V, W, X, Y and Z are each defined above are in each case reacted
&agr;) with acryl halides of the formula (V)
 in which
R
1
is as defined above and
Hal represents halogen (in particular chlorine or bromine)
or
&bgr;) with carboxylic anhydrides of the formula (VI)
R
1
—CO—O—CO—R
1
  (VI)
 in which
R
1
is as defined above,
if appropriate in the presence of a diluent and if appropria

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