Substituted cyclohexene-1,2-dicarboxylic acid derivatives...

Details Substituted cyclohexene-1,2-dicarboxylic acid derivatives... Substituted cyclohexene-1,2-dicarboxylic acid derivatives...

1998-05-29

2001-03-20

Kumar, Shailendra (Department: 1621)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S179000, C548S513000

Reexamination Certificate

active

06204222

ABSTRACT:

DESCRIPTION
Substituted cyclohexene-1,2-dicarboxylic acid derivatives of the general formulae Ia and Ib
in which the variables have the following meaning:
R
1
, R
2
hydrogen,
a C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl group, each of which three groups may furthermore carry from one to three radicals selected from a group consisting of halogen, cyano, amino, thio, hydroxyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylsulfinyl, C
1
-C
6
-alkylsulfonyl, C
1
-C
6
-alkylcarbonyl, carboxyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkylamino, C
1
-C
6
-dialkylamino, C
1
-C
6
-alkylaminocarbonyl, C
1
-C
6
-dialkylaminocarbonyl, C
1
-C
6
-alkylphosphono, C
1
-C
6
-dialkylphosphono, phenyl, 3-membered to 8-membered heterocyclyl which may be saturated or partially or completely unsaturated, it being possible for the heterocycles to carry from one to four hetero atoms selected from a group consisting of from one to four nitrogen atoms, one oxygen atom and one sulfur atom, and it being possible for the phenyl and heterocyclic radicals in turn to carry one of the following substituents on each substitutable atom: hydroxyl, halogen, cyano, nitro, trifluoromethyl, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy,
a C
3
-C
8
-cycloalkyl group, the phenyl group or a saturated or partially or completely unsaturated 3-membered to 8-membered heterocyclyl group, each of which may carry from one to four hetero atoms selected from a group consisting of from one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms, it being possible for the phenyl and heterocyclic groups in turn to carry one of the following radicals on each substitutable carbon atom: hydroxyl, halogen, cyano, nitro, trifluoromethyl, halogen or C
1
-C
6
-alkyl,
and, if R
1
is hydrogen or a C
1
-C
6
-alkyl group, R
2
may additionally be hydroxyl,
a C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy or C
3
-C
6
-alkynyloxy group,
a C
3
-C
7
-cycloalkoxy or C
5
-C
7
-cycloalkenyloxy group,
a C
1
-C
6
-haloalkoxy or C
3
-C
6
-haloalkenyloxy group,
a C
3
-C
7
-cycloalkyl-C
1
-C
6
-alkoxy group,
a C
1
-C
6
-alkylcarbonyloxy group,
a C
1
-C
6
-cyanoalkoxy group,
a hydroxy-C
1
-C
6
-alkoxy, C
1
-C
6
-alkoxy-C
1
-C
6
-alkoxy or C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkoxy group,
a C
1
-C
6
-alkylthio-C
1
-C
6
-alkoxy group,
a C
1
-C
6
-alkylamino-C
1
-C
6
-alkoxy or C
1
-C
6
-dialkylamino-C
1
-C
6
-alkoxy group,
a phenyl-C
1
-C
6
-alkoxy, phenyl-C
3
-C
6
-alkenyloxy or phenyl-C
3
-C
6
-alkynyloxy group, where in each case one or two methylene groups of the alkoxy, alkenyloxy or alkynyloxy chains may be replaced by oxygen, sulfur and/or a C
1
-C
6
-alkylamino chain, and each phenyl ring may be unsubstituted or may carry from one to three radicals selected from a group consisting of C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, halogen, cyano, nitro, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl,
a group —NR
7
R
8
, where R
7
and R
8
, independently of one another are each hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl or phenyl which may be unsubstituted or may carry from one to three radicals selected from a group consisting of C
1
-C
6
-alkyl, halogen, cyano, nitro, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, or
R
7
and R
8
together with the common nitrogen atom may form a saturated or partially or completely unsaturated 4-membered to 7-membered ring which may also contain a further nitrogen atom or an oxygen or sulfur atom as a second ring member,
or
R
1
and R
2
, together with the nitrogen atom to which they are bonded, may form a three-membered to eight-membered saturated or unsaturated, nonaromatic heterocyclic structure which may carry from one to three nitrogen atoms and/or one oxygen or sulfur atom and one or two carbonyl groups, it being possible for the heterocyclic structure to be unsubstituted or to carry from one to three C
1
-C
6
-alkyl radicals;
R
3
is hydrogen or a C
1
-C
6
-alkyl group;
R
4
is hydrogen or halogen;
R
5
is hydrogen, halogen, nitro, cyano or trifluoromethyl;
R
6
is a saturated or partially or completely unsaturated 3-membered to 8-membered heterocyclic group which may carry from one to four hetero atoms selected from a group consisting of from one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms, it being possible for one or two methylene groups of the heterocyclic group to be replaced by carbonyl and for the heterocyclic structure to carry one of the following radicals on each substitutable carbon atom:
C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
3
-C
6
-alkenylthio, C
3
-C
6
-alkynylthio, C
1
-C
6
-alkoxycarbonyl, nitro, amino, halogen, C
1
-C
4
-alkylamino, di-(C
1
-C
4
-alkyl)-amino, cyano, C
1
-C
6
-cyanoalkyl, C
1
-C
6
-haloalkyl or C
1
-C
6
-haloalkoxy,
one of the following groups:
—A—CN or —A—CO—B, —OR
9
, —C(R
10
)═O, —C(R
10
)═S, —C(R
10
)═N—R
16
, —CHR
10
—CHR
11
—CO—B, —C(X
1
R
14
)(X
2
R
15
)R
10
or —P(R
12
)(R
13
)═O, where
A is a straight-chain C
2
-C
4
-alkenylene or C
2
-C
4
-alkynylene chain, both of which may be unsubstituted or may carry one or two radicals selected from a group consisting of halogen, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, hydroxyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylcarbonyloxy, C
1
-C
6
-alkoxycarbonyl and C
1
-C
6
-alkylcarbonyl;
B is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
3
-C
7
-cycloalkyl, —OR
17
or —SR
17
, where R
17
is
hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, phenyl which may be unsubstituted or may carry from one to three radicals selected from a group consisting of C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, halogen, cyano, nitro, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl,
C
1
-C
6
-cyanoalkyl, C
3
-C
6
-haloalkenyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkoximino-C
1
-C
6
-alkyl;
phenyl which may be unsubstituted or may carry from one to three radicals selected from a group consisting of C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, halogen, cyano, nitro, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, di-(C
1
-C
6
-alkoxy)-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, or
—NR
18
R
19
, where R
18
and R
19
, independently of one another, are each hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkylcarbonyl, C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl or phenyl which may be unsubstituted or may carry from one to three radicals selected from a group consisting of C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, halogen, cyano, nitro, C
1
-C
6
-alkoxy and C
1
-C
6
-alkoxycarbonyl, or
R
18
and R
19
, together with the common nitrogen atom, form a saturated or partially or completely unsaturated 4-membered to 7-membered ring which may also contain a further nitrogen atom or an oxygen or sulfur atom as a second ring member;
R
9
is C
1
-C
6
-cyanoalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-haloalkenyl, C
3
-C
6
-alkynyl or C
3
-C
6
-haloalkynyl; phenyl, phenyl-C
1
-C
6
-alkyl, 3-membered to 8-membered heterocyclyl or heterocyclyl-C
1
-C
6
-alkyl, where the heterocyclic structures may be saturated or partially or completely unsaturated and may carry from one to four hetero atoms selected from a group consisting of from one to four nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms, it being possible for the phenyl and heterocyclic radicals in turn to carry one of the following substituents on each substitutable carbon atom: C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, halogen, cyano, nitro, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy or C
1
-C
6
-alkoxycarbonyl, C
1
-C
6
-alkoxycarbonyl-C
2
-C
6
-alkyl,

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