Cyclopentane-1,3-dione derivatives

Details Cyclopentane-1,3-dione derivatives Cyclopentane-1,3-dione derivatives

2002-09-17

2003-05-27

Rotman, Alan L. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S291000, C558S414000, C560S054000, C549S454000

Reexamination Certificate

active

06569810

ABSTRACT:

The present invention relates to novel cyclopentane-1,3-dione derivatives, to processes for their preparation and to their use as herbicides and pesticides.
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-indandione 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). Moreover, 2-(2,4,6-trimethylphenyl)-1,3-indandione is known from the publication J. Economic Entomology, 66, (1973), 584 and the published specification DE 2 361 084, and herbicidal and acaricidal activities are mentioned.
Furthermore, WO 96/01 798 and WO 96/03 366 describe the use of 2-aryl-cyclopentane-1,3-dione derivatives as herbicides and pesticides.
However, the activity of these prior art compounds, in particular at low application weights and concentrations, is not satisfactory in all areas of use. Furthermore, the known compounds do not always have sufficient plant safety with respect to crops.
This invention, accordingly, provides novel bicyclic cyclopentane-1,3-dione derivatives of the formula (I)
in which
X represents halogen, alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro, cyano or respectively optionally substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio,
Y represents hydrogen, halogen, alkyl, alkenyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano,
Z represents halogen, alkyl, alkenyl, alkoxy, alkenyloxy, halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, nitro or cyano, with the proviso that X, Y and Z may not simultaneously represent methyl;
A and Q together represent alkanediyl or alkenediyl, each of which is optionally substituted by halogen, hydroxyl, mercapto, by respectively optionally substituted alkyl, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, and which may additionally contain one of the groups below
 or may be bridged by an alkanediyl group,
B and B′ independently of one another each represent hydrogen, halogen or alkyl or together represent respectively optionally substituted alkanediyl or alkenediyl,
G represents hydrogen (a) or one of the groups
 in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur and
M represents oxygen or sulphur,
R
1
represents respectively optionally substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl, which may contain at least one hetero atom, respectively optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents respectively optionally substituted alkyl, cycloalkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another each represent respectively optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent respectively optionally substituted phenyl, phenylalkyl, phenoxy or phenylthio,
R
6
represents hydrogen, respectively optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, represents respectively optionally substituted cycloalkyl, phenyl or benzyl,
R
7
represents hydrogen or represents respectively optionally halogen-substituted alkyl or alkenyl or
R
6
and R
7
combine with the linking N-atom to form an optionally oxygen- or sulphur-containing and optionally substituted ring,
R
8
and R
9
independently of one another each represent hydrogen or respectively optionally substituted alkyl, phenyl or phenylalkyl, or together represent an optionally substituted alkanediyl radical and
R
10
and R
11
independently of one another each represent respectively optionally halogen-substituted alkyl, alkenyl, alkoxy, alkylamino, dialkylamino, alkenylamino or dialkenylamino or respectively optionally substituted phenyl or benzyl.
Depending on the 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 is meant to be expressed by the dotted line in the formula (I):
The compounds of the formulae (I-A) and (I-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulae (I-A) and (I-B) may optionally be separated by physical methods, for example by chromatographic methods.
For reasons of clarity, hereinbelow only one of the possible isomers is shown in each case. It is implied that the compound in question may be present as a mixture of isomers or in the respective other isomeric form.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of group G, the following principle structures (Ia) to (Ig) result:
in which
A, B, B′, E, L, M, Q, X, Y, Z, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Owing to one or more chiral centres, the compounds of the formula (Ia)-(Ig) are generally obtained as a mixture of stereoisomers. They may be present and used both in the form of their diastereomer mixtures and as pure diastereomers or enantiomers.
Furthermore, it has been found that the novel substituted cyclopentane-1,3-dione derivatives of the formula (I) are obtained by one of the processes described below.
(A) Cyclopentane-1,3-diones or enols thereof of the formula (Ia)
 in which
A, B, B′, Q, X, Y and Z are each as defined above are obtained
when 5-aryl-4-keto-valerates of the formula (II)
 in which
A, B, B′, Q, X, Y and Z are each as defined above, and
R
12
represents alkyl (preferably C
1
-C
6
-alkyl)
 are condensed intramolecularly in the presence of a diluent and in the presence of a base; and
(B) compounds of the formula (Ib)
 in which
A, B, B′, Q, X, Y, Z and R
1
are each as defined above are obtained
when compounds of the formula (Ia)
 in which
A, B, B′, X, Y, Z and Q are each as defined above are reacted
&agr;) with acyl halides of the formula (III)
 in which
R
1
is as defined above and
Hal represents halogen (in particular chlorine and bromine),
 if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder or
&bgr;) with carboxylic anhydrides of the formula (IV)
R
1
—CO—O—CO—R
1
  (IV)
 in which
R
1
is as defined above,
 if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; and
(C) compounds of the formula (Ic-1)
 in which
A, B, B′, Q, X, Y, Z and R
2
are as defined above and
M represents oxygen or sulphur are obtained
when compounds of the formula (Ia)
 in which
A, B, B′, Q, X, Y and Z are each as defined above
are reacted with chloroformic esters or chloroformic thioesters of the formula (V)
 R
2
—M—CO—Cl  (V)
 in which
R
2
and M are each as defined above,
 if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder; and
(D) compounds of the formula (Ic-2)
 in which
A, B, B′, Q, X, Y, Z and R
2
are each as defined above, and
M represents oxygen or sulphur, are obtained,
when compounds of the formula (Ia)
 in which
A, B, B′, Q, X, Y and Z are each as defined above are reacted
&agr;) with chloromonothioformic esters or chlorodithioformic esters of the formula (VI)
 in which
M and R
2
are each as defined above,
 if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder, or
&bgr;) with carbon disulphide and then with alkyl halides of the general formula (VII)
R
2
—Hal  (VII)
 in which
R
2
is as defined above and
Hal represents chlorine, bromine or iodine,
 if appropriate in the presence of a diluent and if appropriate in the presence of a base; and
(E) compounds of the formula (Id)
 in which
A, B, B′, Q, X, Y, Z and R
3
are each as defined above are obtained
when compounds of the formula (Ia)
&e

Affiliated with

Also associated with

Rating

Cyclopentane-1,3-dione derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Cyclopentane-1,3-dione derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyclopentane-1,3-dione derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3082018