Substituted 2-benz(o)ylpyridines, their preparation and...

Details Substituted 2-benz(o)ylpyridines, their preparation and... Substituted 2-benz(o)ylpyridines, their preparation and...

1999-09-15

2002-01-08

Rotman, Alan L. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S342000, C546S343000, C546S344000

Reexamination Certificate

active

06337305

ABSTRACT:

The present invention relates to novel substituted 2-benz(o)ylpyridines of the formula I
where
n is 0 or 1;
X is carbonyl, methylene, CH(C
1
-C
4
-alkyl), CH—OH, CH—CN, CH-halogen, C(halogen)
2
, CH—CONH
2
, CH—CO—O(C
1
-C
4
-alkyl), CH—O(C
1
-C
4
-alkyl) or C(CN) (C
1
-C
4
-alkyl);
R
1
is halogen, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulfinyl or C
1
-C
4
-alkylsulfonyl;
R
2
is hydrogen or halogen;
R
3
is hydrogen, nitro, hydroxyl, halogen, or C
1
-C
4
-alkoxy;
R
4
is hydrogen, nitro, hydroxyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl or C
1
-C
4
-alkoxy;
R
5
is hydrogen, nitro, cyano, halogen, C
1
-C
8
-alkyl, C
3
-C
8
-alkynyl, C
3
-C
8
-alkynyl, C
3
-C
8
-cycloalkyl, C
1
-C
8
-haloalkyl, C
2
-C
8
-haloalkenyl, C
2
-C
8
-haloalkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
2
-C
4
-alkenyloxy-C
1
-C
4
-alkyl, C
2
-C
4
-alkynyloxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, cyano-C
1
-C
8
-alkyl, cyano-C
2
-C
8
-alkenyl, cyano-C
3
-C
8
-alkynyl, —OR
8
, —SR
8
, —SO—R
8
, —SO
2
—R
8
, —SO
2
Cl, —N(R
9
,R
10
), —NH—SO
2
—(C
1
-C
8
-alkyl), —N[—SO
2
—(C
1
-C
8
-alkyl)]
2
, —N(C
1
-C
8
-alkyl)[—SO
2
—(C
1
-C
8
-alkyl)], —SO
2
—N(R
9
,R
10
), —N(R
11
)—CO—R
12
, —NH—CO—OR
8
, —O—CO—NH—R
9
, —O—CO—R
12
, —NH—CO—NH—R
9
, —O—CS—NH
2
, —O—CS—N(C
1
-C
8
-alkyl)
2
, —CO—OR
8
, —CO—N(R
9
,R
10
), —CS—N(R
9
,R
10
), —CO—NH—SO
2
—(C
1
-C
4
-alkyl), —CO—N(C
1
-C
4
-alkyl)—SO
2
—(C
3
-C
4
-alkyl), —CO—R
12
, hydroxycarbonyl-C
1
-C
8
-alkyl, (C
1
-C
8
-alkoxy)carbonyl-C
1
-C
6
-alkyl, —CH
2
—CH(halogen)—CO—OR
8
, —CH
2
—CH(halogen)—CO—N(R
9
,R
10
), —CH
2
—CH(halogen)—CN, —CH
2
—CH(halogen)—CO—(C
1
-C
4
-alkyl), —CH═C(halogen)—CO—OR
8
, —CH═C(C
1
-C
4
-alkyl)—CO—OR
8
, —CH═N—OR
13
, —C(R
14
)═N—OR
13
, —CH(—Y—R
15
, —Z—R
15
), —C(R
14
)(—Y—R
15
, —Z—R
15
),
R
8
is hydrogen, C
1
-C
8
-alkyl, C
3
-C
8
-cycloalkyl, C
1
-C
8
-haloalkyl, cyano-C
1
-C
8
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsufdonyl-C
1
-C
4
-alkyl, C
3
-C
8
-alkenyl, C
5
-C
8
-cycloalkenyl, C
3
-C
8
-haloalkenyl, C
3
-C
8
-alkynyl, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
8
-alkoxy)carbonyl-C
1
-C
6
-alkyl, (C
3
-C
8
-alkenyloxy)carbonyl-C
1
-C
6
-alkyl, (C
3
-C
8
-alkynyloxy)carbonyl-C
1
-C
6
-alkyl, C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
8
-haloalkoxy)carbonyl-C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkyloxy)carbonyl-C
1
-C
6
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
6
-alkenyloxy)carbonyl-C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
6
-alkynyloxy)carbonyl-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, hydroxycarbonyl-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, oxetan-3-yloxycarbonyl-C
1
-C
4
-alkyl, phenoxycarbonyl-C
1
-C
4
-alkyl, benzyl or benzyloxycarbonyl-C
1
-C
4
-alkyl, where each of the phenyl rings of the last 3 radicals may be unsubstituted or may carry one to three substituents, in each case selected from the group consisting of nitro, cyano, hydroxyl, hydroxycarbonyl, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, (C
1
-C
4
-alkoxy)carbonyl and (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkoxy;
R
9
and R
10
independently of one another are each hydrogen, C
1
-C
8
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-alkynyl, C
1
-C
8
-haloalkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfinyl-C
1
-C
4
-alkyl, C
1
-C
4
-alkylsulfonyl-C
1
-C
4
-alkyl, cyano-C
1
-C
8
-alkyl, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
7
-cycloalkyloxy)carbonyl-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
3
-C
7
-cycloalkyl, C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, C
1
-C
6
-alkoxy, phenyl or phenyl-C
1
-C
4
-alkyl, where the phenyl rings of the last two radicals may be unsubstituted or may carry one to three substituents, in each case selected from the group consisting of nitro, cyano, hydroxyl, halogen, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, (C
1
-C
4
-alkoxy)carbonyl and (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkoxy;
or R
9
and R
10
together are a tetramethylene, pentamethylene or ethyleneoxyethylene chain, each of which may carry a hydroxycarbonyl group or a (C
1
-C
6
-alkoxy)carbonyl radical;
R
11
is hydrogen, C
1
-C
8
-alkyl, C
3
-C
8
-alkenyl or C
3
-C
8
-alkynyl;
R
12
and R
13
independently of one another are each hydrogen, C
1
-C
8
-alkyl, C
3
-C
8
-alkenyl, C
3
-C
8
-alkynyl, C
1
-C
8
-haloalkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl, C
3
-C
8
-cycloalkyl, phenyl or phenyl-C
1
-C
4
-alkyl, where the phenyl rings of the last two radicals may be unsubstituted or may carry one to three substituents, in each case selected from the group consisting of nitro, cyano, hydroxyl, hydroxycarbonyl, halogen, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, (C
1
-C
4
-alkoxy)carbonyl and (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkoxy;
R
14
is C
1
-C
8
-alkyl;
Y and Z independently of one another are each oxygen or sulfur;
R
15
is C
1
-C
8
-alkyl, C
1
-C
8
-haloalkyl or C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl;
R
16
-R
21
independently of one another are each hydrogen, cyano, C
1
-C
8
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
8
-alkoxy, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxy, hydroxycarbonyl, (C
1
-C
8
-alkoxy)carbonyl, aminocarbonyl, (C
1
-C
8
-alkyl)aminocarbonyl or di(C
1
-C
8
-alkyl)aminocarbonyl;
R
22
-R
25
independently of one another are each hydrogen, C
1
-C
8
-alkyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
3
-C
8
-alkenyl or C
3
-C
8
-alkynyl and
R
26
-R
28
independently of one another are each hydrogen or C
1
-C
8
-alkyl;
R
6
is hydrogen, nitro, halogen, —OR
29
or —CO—OR
29
and
R
7
is hydrogen, nitro, halogen or —OR
30
, where
R
29
and R
30
each have one of the meanings of R
8
,
and the agriculturally useful salts of the compounds I, except for those compounds I, where X is methylene and
R
5
is —OR
8
and R
3
and R
7
are both hydrogen or
R
1
is halogen and R
3
, R
4
, R
6
and R
7
are all simultaneously hydrogen.
Furthermore, the invention relates to
the use of the compounds I as herbicides or for the dessication/defoliation of plants,
herbicidal compositions and compositions for the dessication and/or defoliation of plants which comprise compounds I as active ingredients,
methods for controlling undesirable vegetation and for the dessication and/or defoliation of plants using the compounds I and
processes for preparing the compounds I and the herbicidal compositions and compositions for the dessication and/or defoliation of plants using the compounds I.
EP-A 047 972 describes phenoxyalkanoic acid derivatives for increasing the carbohydrate depositing in plants whose general formula—if the variables are appropriately chosen—also includes compounds I where n=0, X methylene, R
1
=halogen, di- or trifluoromethyl, R
2
=fluorine or chlorine, R
3
, R
4
, R
6
and R
7
=hydrogen and R
5
=ethoxy, 2-butoxy or but-3-en-2-yloxy, in each case substituted with a hydroxycarbonyl radical or certain ester, thioester or carboxamide radicals.
Those 2-benzylpyridines I where n=0, X=methylene, R
1
=halogen or trifluoromethyl, R
3
, R
4
and R
7
=hydrogen, R
5
=ethoxy, 2-butoxy or but-3-en-2-yloxy, each of which carries a certain carboxamide group, and R
6
=hydrogen or halogen are included in the general formula of the herbicides and fungicides disclosed in DE-A 29 48 095.
The Swiss Patent CH 642 075 discloses a compound where n=0, X=methylene, R
1
=chlorine, R
2
=hydrogen, R
3
, R
4
, R
6
and R
7
=hydrogen and R
5
=2-(ethoxycarbonyl)but-2-yloxy which is said to have pharmaceutical activity.
Benz(o)ylpyridines of the type of the compounds I are also included in the general formulae of the

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