Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-08-31
2001-06-26
Padmanabhan, Sreeni (Department: 1621)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S307000, C504S310000, C504S314000, C514S478000, C514S512000, C514S513000, C514S520000, C514S683000, C514S684000, C558S070000, C558S194000, C560S024000, C560S029000, C560S107000, C560S179000, C560S205000, C560S302000, C562S459000, C568S309000, C568S310000, C568S327000, C568S328000, C568S329000, C568S330000
Reexamination Certificate
active
06251833
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel 2-aryl-3-hydroxy-&Dgr;
2
-cyclopentene-1-one derivatives, to processes for their preparation and to their use as herbicides and pesticides.
BACKGROUND OF THE INVENTION
It is known that certain substituted 2-arylcyclopentane diones 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, 4,632,698, WO 96/01798 and WO 96/03366). Moreover, compounds which are substituted in a similar manner are known; 3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-ene-1-one from the publication Micklefield et al., Tetrahedron, (1992), 7519-26 and the natural compound involutin (−)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-enone from the publication Edwards et al., J. Chem. Soc. S, (1967), 405-9. An insecticidal or acaricidal action has not been described.
However, the acaricidal and insecticidal activity and/or activity spectrum, and the compatibility of these compounds with plants, in particular crop plants, is not always satisfactory.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel compounds of the formula (I)
in which
W represents hydrogen, cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenalkyl, halogenalkoxy, in each case optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,
X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenalkyl, halogenoalkoxy, cyano, nitro, in each case optionally substituted phenyl, phenylalkyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, with the proviso that at least one of the substituents W and X does not represent hydrogen,
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- or 6-membered hetaryloxy, 5- or 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or
Y and Z together with the carbon atoms to which they are attached represent an optionally substituted ring which is optionally interrupted by one or more heteroatoms, where X and W have one of the meanings mentioned above, or
W and Z together with the carbon atoms to which they are attached represent an optionally substituted ring which is optionally interrupted by one or more heteroatoms, where X and Y have one of the meanings mentioned above,
A represents hydrogen or represents alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, each of which is optionally mono- or polysubstituted by identical or different halogens, represents saturated or unsaturated, unsubstituted or substituted cycloalkyl which is optionally interrupted by one or more heteroatoms or represents phenyl or phenylalkyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cyano and nitro,
B represents alkyl or alkoxyalkyl,
or
A and B together with the carbon atom to which they are attached form a saturated or unsaturated, optionally substituted ring which is optionally interrupted by one or more heteroatoms,
or
A and B together with the carbon atom to which they are attached form a ring where two substituents together with the carbon atoms to which they are attached form a saturated or unsaturated ring which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, alkyl and alkoxy and which may contain oxygen or sulphur,
D
1
and D
2
independently of one another each represent hydrogen, halogen, optionally halogen-substituted alkyl or optionally substituted phenyl,
G represents hydrogen (a) or represents one of the groups
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 mono- or polysubstituted by identical or different halogens, or represents optionally substituted, saturated or unsaturated cycloalkyl which may be interrupted by one or more heteroatoms, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, each of which is optionally mono- or polysubstituted by identical or different halogens, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
represents alkyl which is optionally mono- or polysubstituted by identical or different halogens or represents in each case optionally substituted phenyl or phenylalkyl,
R
4
and R
5
independently of one another each represent alkyl, alkoxy, alkylamino, alkenylamino, dialkylamino, dialkenylamino, alkylthio, alkenylthio, alkinylthio, cycloalkylthio, each of which is optionally mono- or polysubstituted by identical or different halogens, or represents in each case optionally substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another each represent hydrogen, represent alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of which is optionally mono- or polysubstituted by identical or different halogens, or represent optionally substituted phenyl or optionally substituted benzyl,
or together with the N atom to which they are attached form an optionally substituted ring which optionally contains oxygen or sulphur,
and the enantiomerically pure forms of compounds of the formula (I).
Depending, inter alia, on the nature of the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of different composition which are separated, if appropriate, in a customary manner by physical methods, for example by chromatographic methods.
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 -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 the group G, the following principal structures (Ia) to (Ig) result:
in which
A, B, D
1
, D
2
, E, L, M, W, X, Y, Z, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
are each as defined above.
Furthermore, it has been found
(A) that compounds of the formula (IA)
in which
A, B, D
1
, D
2
, W, X, Y and Z are each as defined above
are obtained when
ketocarboxylic esters of the formula (II)
in which
A, B, D
1
, D
2
, W, X, Y and Z are each as defined above and
R
8
represents alkyl (in particular C
1
-C
8
-alkyl)
are cyclized intramolecularly, if appropriate in the presence of a diluent and in the presence of a base, and
(B) that the compounds of the formula (Ib) shown above, in which A, B, D
1
, D
2
, R
1
, W, X, Y and Z are each as defined above, are obtained when compounds of the formula (Ia) shown above, in which A, B, D
1
, D
2
, W, X, Y and Z 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 or bromine)
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;
(C) that the compounds of the formula (Ic) shown above, in which A, B, D
1
, D
2
, R
2
, W, M,
Erdelen Christoph
Fischer Reiner
Graff Alan
Mencke Norbert
Turberg Andreas
Gil Joseph C.
Padmanabhan Sreeni
Zurcher Jackie Ann
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