Use of derivatives of 2-oxopyrrole as crop protection agents...

Details Use of derivatives of 2-oxopyrrole as crop protection agents... Use of derivatives of 2-oxopyrrole as crop protection agents...

2001-01-24

2003-04-15

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C424S409000, C514S423000, C548S531000

Reexamination Certificate

active

06548451

ABSTRACT:

This application is a 371 of PCT/EP99/02006 Mar. 24, 1999.
The present invention relates to the use of 2-oxopyrrole derivatives of the formula I as crop protection agents
Furthermore, the invention relates to novel 2-oxopyrrole derivatives of the formula I.
2-Oxopyrroles of the formula I in which R
1
is phenyl, 4-dimethylaminophenyl or 2-nitrophenyl, R
2
is methyl and A is COOC
2
H
5
are known from Z. Physiol. Chem. 132 (1924), 72. A possible use as crop protection agents is not mentioned.
It is an object of the present invention to provide compounds which are active as crop protection agents.
We have found that this object is achieved by the use according to the invention as claimed in claim 1.
Some of the 2-oxopyrrole derivatives to be used according to the invention are novel and as such also form part of the subject matter of the invention.
Preferred embodiments of the invention can be found in the subclaims and the detailed description below.
In the 2-oxopyrrole derivatives of the formula I to be used according to the invention, R
1
, R
2
and A have the following meanings:
R
1
is aryl or heteroaryl, where these radicals independently of one another may carry one to five of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C
1
-C
6
-alkyl, C
1
-C
6
-cyanoalkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkynyl, C
3
-C
6
-alkynyl-C
1
-C
6
-alkoxy, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkoxy-C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkyloxy, C
3
-C
7
-cyanocycloalkyloxy, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkyloxy, C
3
-C
7
-halocycloalkyl, C
3
-C
7
-cyanocycloalkyl, C
3
-C
7
-halocycloalkyloxy, C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkyl-C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkoxy-C
5
-C
7
-cycloalkenyl, C
5
-C
7
-cyanocycloalkenyl, C
5
-C
7
-halocycloalkenyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
l
-C
6
-haloalkyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl, C
2
-C
6
-cyanoalkenyl, C
3
-C
6
-cyanoalkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-cyanoalkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-cyanoalkenyloxy, C
2
-C
6
-haloalkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-cyanoalkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylcarboxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl, aryl-C
1
-C
6
-alkyl, aryl-C
2
-C
6
-alkenyl, aryl-C
3
-C
6
-alkynyl, heteroaryl-C
1
-C
6
-alkyl, heteroaryl-C
2
-C
6
-alkenyl, heteroaryl-C
3
-C
6
-alkynyl, aryl-C
1
-C
6
-alkoxy, aryl-C
2
-C
6
-alkenyloxy, aryl-C
3
-C
6
-alkynyloxy, heteroaryl-C
1
-C
6
-alkoxy, heteroaryl-C
2
-C
6
-alkenyloxy, heteroaryl-C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
2
-C
6
-alkenylsulfinyl, C
2
-C
6
-alkenylsulfonyl, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, HC═NOH, C
1
-C
6
-alkyl-C═NOH, HC═N—O—C
1
-C
6
-alkyl, HC═N—O—C
1
-C
6
-alkyl-aryl, C
1
-C
6
-alkyl-C═N—O—C
1
-C
6
-alkyl, HC═N—O—C
2
-C
6
-alkenyl, C
1
-C
6
-alkyl-C═N—O—C
2
-C
6
-alkenyl, HC═N—O-aryl, C
1
-C
6
-alkyl-C═N—O-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio, where the cyclic substituents for their part may, independently of one another, carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxyl, mercapto, thiocyanato, carboxyl, amino, C
1
-C
6
-alkyl, C
1
-C
6
-cyanoalkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy-C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkynyl, C
3
-C
6
-alkynyl-C
1
-C
6
-alkoxy, C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkyl, C
1
-C
6
-alkoxy-C
3
-C
7
-cycloalkyl, C
3
-C
7
-cycloalkyloxy, C
3
-C
7
-cyanocycloalkyloxy, C
1
-C
6
-alkyl-C
3
-C
7
-cycloalkyloxy, C
3
-C
7
-halocycloalkyl, C
3
-C
7
-cyanocycloalkyl, C
3
-C
7
-halocycloalkyloxy, C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkyl-C
5
-C
7
-cycloalkenyl, C
1
-C
6
-alkoxy-C
5
-C
7
-cycloalkenyl, C
5
-C
7
-cyanocycloalkenyl, C
5
-C
7
-halocycloalkenyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-haloalkenyl, C
3
-C
6
-haloalkynyl, C
2
-C
6
-cyanoalkenyl, C
3
-C
6
-cyanoalkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-cyanoalkoxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-cyanoalkenyloxy, C
2
-C
6
-haloalkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkylthio, C
1
-C
6
-cyanoalkylthio, C
1
-C
6
-haloalkylthio, C
1
-C
6
-alkoxy-C
1
-C
6
-alkylthio, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkylcarboxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylcarbonylamino, arylcarbonylamino, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl, aryl-C
1
-C
6
-alkyl, aryl-C
2
-C
6
-alkenyl, aryl-C
3
-C
6
-alkynyl, heteroaryl-C
1
-C
6
-alkyl, heteroaryl-C
2
-C
6
-alkenyl, heteroaryl-C
3
-C
6
-alkynyl, aryl-C
1
-C
6
-alkoxy, aryl-C
2
-C
6
-alkenyloxy, aryl-C
3
-C
6
-alkynyloxy, heteroaryl-C
1
-C
6
-alkoxy, heteroaryl-C
2
-C
6
-alkenyloxy, heteroaryl-C
3
-C
6
-alkynyloxy, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
2
-C
6
-alkenylsulfinyl, C
2
-C
6
-alkenylsulfonyl, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, HC═NOH, C
1
-C
6
-alkyl-C═NOH, HC═N—O—C
1
-C
6
-alkyl, HC═N—O—C
1
-C
6
-alkyl-aryl, C
1
-C
6
-alkyl-C═N—O-C
1
-C
6
-alkyl, HC═N—O—C
2
-C
6
-alkenyl, C
1
-C
6
-alkyl-C═N—O—C
2
-C
6
-alkenyl, HC═N—O-aryl, C
1
-C
6
-alkyl-C═N—O-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio; or
where the aryl or heteroaryl radical forms a bicyclic system with a fused-on phenyl ring, a fused-on C
3
-C
6
-carbocycle or a 5- or 6-membered heterocycle, where the fused-on ring system may carry one to three of the substituents mentioned above for aryl;
R
2
is C
1
-C
6
-alkyl or aryl or heteroaryl, where aryl, heteroaryl may carry one to three of the substituents mentioned under R
1
for aryl, is C
3
-C
7
-cycloalkyl or C
1
-C
6
-alkylaryl;
A is COOR
3
or CONR
3
R
4
, where R
3
and R
4
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
3
-C
7
-cycloalkyl or C
1
-C
6
-alkyl-aryl, which may be partially or fully halogenated or may carry one to three substituents selected from the group consisting of C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
3
-C
7
-cycloalkyl, C
5
-C
7
-cycloalkenyl.
With respect to the position of the substituent R
1
, the 2-oxopyrrole derivatives to be used according to the invention can be employed as E or as Z isomers or as mixtures of the two isomers.
Except for the compounds below, the 2-oxopyrrole derivatives of the formula I to be used according to the invention are novel and are in their own right part of the subject matter of the invention:
R
1
R
2
A
C
6
H
5
CH
3
COOC
2
H
5
4-(CH
3
)
2
N—C
6
H
4
CH
3
COOC
2
H
5
2-NO
2
—C
6
H
4
CH
3
COOC
2
H
5
4-NO
2
—C
6
H
4
CH
3
COOC
2
H
5
4-Cl—C
6
H
4
CH
3
COOC
2
H
5
4-Br—C
6
H
4
CH
3
COOC
2
H
5
4-CH
3
—C
6
H
4
CH
3
COOC
2
H
5
4-HO—C
6
H
4
CH
3
COOC
2
H
5
2,4-(CH
3
)
2
-5-COOCH
2
CH
3
-pyrrol-3-yl
CH
3
COOC
2
H
5
3,5-(CH
3
)
2
-4-COOCH
2
CH
3
-pyrrol-2-yl
CH
3
COOC
2
H
5
C
6
H
5
C
6
H
5
COOCH
3
2-COOCH
2
CH
3
-5-CH
3
O-indol-3-yl
CH
3
COOC
2
H
5
4-CH
3
O—C
6
H
4
CH
3
COOC
2
H
5
The organic molecular moieties mentioned in the definitions of R
1
, R
2
and A are collective terms for individual enumerations of the individual meanings. All carbon chains, i.e. all alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and alkynylthio moieties may be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.
The term “halogen” in each case means fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.

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