2-(2,4,6-trimethyl phenyl)cyclopentane-1,3-dione derivatives

Details 2-(2,4,6-trimethyl phenyl)cyclopentane-1,3-dione derivatives 2-(2,4,6-trimethyl phenyl)cyclopentane-1,3-dione derivatives

1997-01-15

1998-09-15

Lambkin, Deborah C.

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

Organic compounds

Carboxylic acid esters

568327, 564263, 564250, 564180, 558214, 504313, 504348, 504344, 504343, 504336, 504290, 504295, 504194, 549 39, 549453, C07C 6900, C07C31500, A01N 3712, A01N 3106

Patent

active

058081356

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/02684 filed Jul. 11, 1995.
The present invention relates to novel 2-aryl-3-hydroxy-.DELTA..sup.2 -cyclopenten-1-one derivatives, processes for their preparation and their use as herbicides and agents for controlling pests.
It is known that certain substituted 2-arylcyclopentanediones, such as, for example, 2-(2',4'-dimethylphenyl)-4,5,6,7,8,9-hexahydro-1,3-indanedione, have herbicidal and acaricidal properties (cf., for example, U.S. Pat. Nos. 4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547 and 4,626,698). 2-(2,4,6-trimethylphenyl)-1,3-indanedione is furthermore known from the publication J. Economic Entomology, 66, (1973), 584 and the laid-open specification DE 2 361 084, with mention of herbicidal and acaricidal actions.
However, the activity of these known compounds is not completely satisfactory in all fields of use, especially when low amounts and concentrations are applied.
Novel substituted bicyclic 2-mesityl-cyclopentane-1,3-dione derivatives of the formula (I) ##STR3## in which A and Q together represent alkanediyl or alkenediyl, which is in each case optionally substituted by halogen, hydroxyl, mercapto or in each case optionally substituted alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, and which furthermore optionally contains one of the following groups ##STR4## or is bridged by an alkanediyl group, B and B' independently of one another represent hydrogen, halogen or alkyl, or together represent in each case optionally substituted alkanediyl or alkenediyl, ##STR5## in which E represents a metal ion equivalent or an ammonium ion, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl, which can contain at least one heteroatom, or in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or in each case optionally substituted phenyl or benzyl, phenylalkyl, optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkyl amino, alkylthio, alkenylthio, cycloalkylthio, or represent in each case optionally substituted phenyl, phenoxy or phenylthio, alkyl, alkenyl or alkoxyalkyl, or represents optionally substituted phenyl, or represents in each case optionally substituted cycloalkyl or benzyl, alkyl or alkenyl, or represent a ring which optionally contains oxygen or sulphur, each case optionally substituted alkyl, phenyl or phenylalkyl, or together represent an optionally substituted alkanediyl radical and optionally halogen-substituted alkyl, alkenyl, alkoxy, alkylamino, dialkylamino, alkenylamino or dialkenylamino or in each case optionally substituted phenyl or benzyl, have now been found.
Depending on a position of the substituent G, the compounds of the formula (I) can be present in the two isomeric forms of the formulae (I-A) and (I-B), which the broken line in the formula (I) is intended to illustrate: ##STR6##
The compounds of the formula (I-A) and (I-B) can be present both as mixtures and in the form of their pure isomers. If appropriate, mixtures of the compounds of the formulae (I-A) and (I-B) can be separated by physical methods, for example by chromatographic methods.
For better clarity, in each case only one of the possible isomers is shown below. This does not mean that the compound in question cannot be present, where appropriate, as an isomer mixture or in the other particular isomeric form.
Incorporating the various meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following main structures (Ia) to (Ig) result: ##STR7## wherein A, B, B', E, L, M, Q, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the abovementioned meanings.
Because of one or more chirality centres, the compounds of the formula (Ia)-(Ig) are in general obtained as a stereoisomer mixture. They can be present and used both in the form of their diastereomer mixtures and as pure diastereomers or enantiomers.
It has furthermore been found that the novel substituted 2-mesityl-cyclopentane-1,3-dione derivatives of the formula (I) are obtained by one

REFERENCES:
patent: 4283348 (1981-08-01), Wheeler
patent: 4436666 (1984-03-01), Wheeler

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