Alkyl dihalogenated phenyl-substituted ketoenols useful as...

Details Alkyl dihalogenated phenyl-substituted ketoenols useful as... Alkyl dihalogenated phenyl-substituted ketoenols useful as...

1997-10-31

2001-11-13

Shah, Mukund J. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S412000, C514S425000, C524S570000, C524S571000, C524S572000, C524S573000, C548S428000, C548S512000, C548S518000, C548S543000, C548S563000

Reexamination Certificate

active

06316486

ABSTRACT:

The invention relates to new phenyl-substituted cyclic ketoenols, to a plurality of processes and intermediates for their preparation, and to their use as pesticides and herbicides.
3-Acyl-pyrrolidine-2,4-diones have already been described as having pharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenylpyrrolidine-2,4-diones were synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). A biological activity of these compound has not been described.
EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of a similar structure (3-aryl-pyrrolidine-2,4-diones), which, however, have not been disclosed as having a herbicidal, insecticidal or acaricidal action. Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A442 077) having a herbicidal, insecticidal or acaricidal action are known.
Also known are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and 1H-arylpyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, WO 94/01 997, WO 93/26954 and WO 95/01 358).
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 used as starting compounds (such as, for example, 3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-&Dgr;
3
-dihydrofuran-2-one) 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, but no mention is made of insecticidal and/or acaricidal activity. 3-Aryl-&Dgr;
3
-dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are furthermore known from EP-A-528 156, but the action described in this publication is not always sufficient. Thiotetronic acids are known from WO 95/26345.
Furthermore, certain 3H-pyrazole-3-one derivatives, such as, for example, 1,2-diethyl-1,2-dihydro-5-hydroxy4-phenyl-3H-pyrazol-3-one or {[5-oxo-1,2-diphenyl-4-(p-sulphophenyl)-3-pyrazolin-3-yl]-oxy}-disodium salt or p-(3-hydroxy-5-oxo-1,2-diphenyl-3-pyrazolin-4-yl)-benzenesulphonic acid are known from the literature (cf. J. Heterocycl. Chem., 25(5), 1301-1305, 1988 or J. Heterocycl. Chem. 25(5), 1307-1310, 1988 or Zh. Obshch. Khim., 34(7), 2397-2402, 1964). However, a biological action of these compounds is not described.
It is furthermore known that the trisodium salt of 4,4′,4″-(5-hydroxy-3-oxo-1H-pyrazol-1,2,4(3H)-triyl)-tris-benzenesulphonic acid has pharmacological properties (cf. Farmakol. Toksikol. (Moscow), 38(2), 180-186, 1976). However, its use in plant protection is not known.
Moreover, 4-arylpyrazolidine-3,5-dione derivatives having herbicidal, acaricidal and insecticidal properties are described in EP-A-508 126 and in WO 92/16 510.
Certain phenyl-pyrone derivatives which are unsubstituted in the phenyl ring have already been described (cf. A. M. Chirazi, T. Kappe and E. Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K. Heidenbluth, Chem. Ber. 91, 2849), a potential use of these compounds as pesticides not being indicated. Phenyl-pyrone derivatives which are substituted in the phenyl ring and have herbicidal, acaricidal and insecticidal properties are described in EP-A-588 137.
Certain 5-phenyl-1,3-thiazine derivatives which are unsubstituted in the phenyl ring have already been described (cf. E. Ziegler and E. Steiner, Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J. Heterocycl. Chem. 10, 223 (1973)), a potential use of these compounds as pesticides not being indicated. 5-Phenyl-1,3-thiazine derivatives which are substituted in the phenyl ring and have a herbicidal, acaricillal and insecticidal action are described in WO 94/14 785.
However, the activity and spectrum of action of these compounds are not always entirely satisfactory, in particular at low application rates and concentrations. Furthermore, the tolerance, by plants, of the known compounds is not always sufficient.
There have now been found new compounds of the formula (I)
in which
X represents halogen,
Y represents halogen or alkyl and
Z represents halogen or alkyl,
with the proviso that always one of the radicals Y and Z represents halogen and the other represents alkyl,
Het represents one of the groups
in which
A represents hydrogen, or represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which is optionally substituted by halogen, or represents in each case saturated or unsaturated and optionally substituted cycloalkyl or heterocyclyl, or represents aryl, arylalkyl or hetaryl, each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cyano or nitro,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B together with the carbon atom to which they are bonded represent a saturated or unsaturated, optionally substituted carbocycle or heterocycle,
D represents hydrogen or an optionally substituted radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl or hetaryl, or
A and D together with the atoms to which they are bonded represent a saturated or unsaturated and optionally substituted carbocycle or heterocycle,
G, in the event that Het represents one of the radicals (1), (2), (3), (5) or (6) represents hydrogen (a) or, in the event that Het represents one of the radicals (1), (2), (3), (4), (5) or (6), 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 cycloalkyl or heterocyclyl, each of which is optionally substituted by halogen, alkyl or alkoxy, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, each of which is optionally substituted by halogen, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another represent alkyl, alkoxy, alkylainino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, each of which is optionally substituted by halogen, or in each case represent optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent hydrogen, or represent alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, each of which is optionally substituted by halogen, or represent in each case optionally substituted phenyl or benzyl, or together with the N atom to which they are bonded represent an optionally substituted cycle which optionally contains oxygen or sulphur.
Depending on the nature of the substituents, the compounds of the formula (I) can exist as geometric and/or optical isomers or variously composed isomer mixtures which, if desired, can be separated in the customary manner. The pure isomers and the isomer mixtures, their preparation and their use, and the compositions comprising them are all objects of the present invention. For the sake of simplicity, however, the following text will always mention compounds of the formula (I), even though this is to be understood as meaning the pure compounds and, if appropriate, also mixtures containing various proportions of isomeric compounds.
Taking into consideration the meanings (1) to (6) of the group Het, the following main structures (I-1) to (I-6) result:
in which
A, B, D, G, X, Y and Z have the abovementioned meanings.
Taking into consideration the various meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (I-1-a) to (I-1-g) result if H

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