2,4,5-trisubstituted phenylketo-enols for use as pesticides...

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

Reexamination Certificate

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C514S473000, C549S477000

Reexamination Certificate

active

06511942

ABSTRACT:

The invention relates to new phenyl-substituted cyclic ketoenols, several processes and intermediate products for their preparation and their use as pest control agents and herbicides.
It has already been disclosed that certain phenyl-substituted cyclic ketoenols are active as insecticides, acaricides and/or herbicides.
Pharmaceutical properties have already been described for 3-acyl-pyrrolidine-2,4-diones (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have been synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). No biological activity has been described for these compounds.
EP-A-0 262 399 and GB-A-2 266 888 disclose compounds of similar structure (3-aryl-pyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal action has been disclosed. Known compounds which have a herbicidal, insecticidal or acaricidal action are unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).
Compounds which are furthermore 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, DE 44 40 594, WO 94/01 997 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 likewise described in DE-A-4 014 420. Compounds of similar structure, without an insecticidal and/or acaricidal activity being mentioned, are known from the publication Campbell et al., J. Chem. Soc., Perkin Trans. 1, 1985, (8) 1567-76. 3-Aryl-&Dgr;
3
-dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are furthermore known from EP-A-528 156, EP-A 0 647 637 and WO 95/26345.
Certain phenyl-pyrone derivatives which are unsubstituted in the phenyl ring have already been disclosed (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), no possible usefulness of these compounds as pest control agents being mentioned. 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 disclosed (cf. E. Ziegler and E. Steiner, Monatsh. 95 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J. Heterocycl. Chem. 10, 223 (1973)), no possible use as pest control agents being mentioned for these compounds. 5-Phenyl-1,3-thiazine derivatives which are substituted in the phenyl ring and have a herbicidal, acaricidal and insecticidal action are described in WO 94/14 785.
However, the acaricidal and insecticidal activity and/or range of action and the plant tolerance of these compounds, in particular with respect to crop plants, is not always adequate.
New compounds of the formula (I)
in which
X represents halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro,
Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro,
Z represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or in each case optionally substituted phenoxy, phenylthio, 5- to 6-membered hetaryloxy, 5- to 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio or
Y and Z, together with the carbon atom to which they are bonded, represent a cyclic radical which is optionally substituted and optionally interrupted by heteroatoms, wherein X has one of the abovementioned meanings,
Het represents one of the groups
 wherein
A represents hydrogen, or represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl which are in each case optionally substituted by halogen, or represents in each case saturated or unsaturated and optionally substituted cycloalkyl or heterocyclyl, or represents aryl, arylalkyl or hetaryl which are in each case 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 carbocyclic or heterocyclic radical,
D represents hydrogen, or represents 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 carbocyclic or heterocyclic radical which is in each case optionally substituted,
G represents hydrogen (a), or represents one of the groups
 wherein
E represents one 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 which are in each case optionally substituted by halogen, or represents cycloalkyl or heterocyclyl which are in each case 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 which are in each case 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, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio which are in each case optionally substituted by halogen, or represent in each case optionally substituted phenyl, phenoxy or phenylthio, and
R
6
and R
7
independently of one another represent hydrogen, or represent alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl which are in each case 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, form a cyclic radical which optionally contains oxygen or sulphur and is optionally substituted, have now been found.
The compounds of the formula (I) can be in the form of geometric and/or optical rat isomers or isomer mixtures of varying composition, also depending on the nature of the substituents, and these can optionally be separated in the customary manner. The present invention relates both to the pure isomers and to the isomer mixtures, their preparation and use and compositions comprising them. For simplicity, however, reference is always made below to compounds of the formula (I), although this means both the pure compounds and, where appropriate, also mixtures with different contents of isomeric compounds.
Incorporating the meanings (1) to (5) of the group Het, the following main structures (I-1) to (I-5) result:
wherein
A, B, D, G, x, Y and Z have the abovementioned meaning.
Incorporating the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following main structures (I-1-a) to (I-1-g) result if Het represents the group (1)
wherein
A, B, E, L, M, X, Y, Z, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
have the abovementioned meanings.
Incorporating the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following main structures (I-2-a) to (I-2-g) result if Het represents the group (2)
wherein
A, B, E, L, M, X, Y, Z, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
have the abovementioned meaning.
Incorporating the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following main structures (I-3-a) to (I-3-g) result if Het represents the group (3)
wherein
A, B, E, L, M, X, Y, Z. R

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