3-aryl-tetronic acid derivatives, the production thereof and the

Details 3-aryl-tetronic acid derivatives, the production thereof and the 3-aryl-tetronic acid derivatives, the production thereof and the

1997-06-17

1998-11-03

Dentz, Bernard

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

504129, 504140, 546 16, 546 19, 5483007, 548410, 549 13, 549 22, 549 39, 549 60, 549265, 544230, C07D49310, C07D49510, C07D491107, A01N 4308

Patent

active

058308253

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/04869 filed Dec. 11, 1995.
The present invention relates to new 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydro-furanone derivatives (3-aryl-tetronic acid derivatives), to processes for their preparation, and to their use as pesticides.
It has been disclosed that certain substituted .DELTA..sup.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)-.DELTA..sup.3 -dihydrofuran-2-one) is also described in DE-A-4 014 420. Compounds of a similar structure are known from the publication of Campbell et al., J. Chem. Soc., Perkin Trans. 1, 1985, (8) 1567-76, without an insecticidal and/or acaricidal activity being mentioned. Furthermore, 3-aryl-.DELTA..sup.3 -dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are disclosed in EP-528 156, but the action described therein is not always sufficient.
There have now been found new 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydrofuranone derivatives of the formula (I) ##STR3## in which A and B together with the carbon atom to which they are bonded form an unsubstituted or substituted 5- to 7-membered ring which is interrupted by at least one hetero atom, ##STR4## E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulphur, polyalkoxyalkyl, each of which is optionally substituted by halogen, or represents cycloalkyl which can be interrupted by at least one hetero atom and which is optionally substituted by halogen, alkyl or alkoxy, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, which is optionally substituted by halogen, or represents cycloalkyl which is optionally substituted by halogen, alkoxy or alkyl, or represents in each case optionally substituted phenyl or benzyl, alkoxy, alkylamino, dialkylamino, alkyltio, alkenylthio or cycloalkylthio, each of which is optionally substituted by halogen, or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and 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 represent an alkanediyl radical which is optionally interrupted by oxygen or sulphur.
Taking into consideration the various meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (Ia) to (Ig) result: ##STR5## in which
A, B, E, L, M, X, Y, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and n have the abovementioned meanings.
Due to one or more chiral centres, the compounds of the formulae (Ia) to (Ig) are generally obtained in the form of a stereoisomer mixture. They can be used in the form of their diastereomer mixtures, but also in the form of pure diastereomers or enantiomers.
Furthermore, it has been found that the new substituted 3-aryl-tetronic acid derivatives of the formula (I) are obtained by one of the processes described hereinbelow. ##STR6## in which A, B, X, Y, Z and n have the abovementioned meanings, ##STR7## in which A, B, X, Y, Z and n have the abovementioned meanings and a diluent and in the presence of a base; and ##STR8## in which A, B, X, Y, Z, R.sup.1 and n have the abovementioned meanings, ##STR9## in which A, B, X, Y, Z and n have the abovementioned meanings, are reacted ##STR10## in which R.sup.1 has the abovementioned meanings and presence of an acid-binding agent, presence of an acid-binding agent, ##STR11## in which A, B, X, Y, Z, R.sup.2 and n have the abovementioned meanings and ##STR12## in which A, B, X, Y, Z and n have the abovementioned meanings, formula (V) presence of an acid-binding agent; ##STR13## in which A, B, R.sup.2, X, Y, Z and n have the abovementioned meanings and ##STR14## in which A, B, X, Y, Z and n have the abovementioned meanings, are reacted the formula (VI) ##STR15## in which M and

REFERENCES:
patent: 5262383 (1993-11-01), Fischer et al.

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