Substituted phenyl derivatives

Details Substituted phenyl derivatives Substituted phenyl derivatives

2002-12-13

2004-06-15

Seaman, D. Margaret (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S366100, C548S370400, C548S370700

Reexamination Certificate

active

06750222

ABSTRACT:

It is known that substituted phenyl derivatives can have herbicidal and plant-growth-regulating properties (cf., for example, DE 3602-379-A, JP 10007657, U.S. Pat. No. 5,698,495, U.S. Pat. No. 5,786,392, WO 9718196). However, on application, these compounds frequently have disadvantages, such as, for example, long persistency, insufficient selectivity in important crops of useful plants or lack of activity against harmful plants.
This invention now provides phenyl derivatives substituted in a particular manner which can be used advantageously as herbicides and plant growth regulators.
Accordingly, the present invention provides compounds of the formula (I) and/or salts thereof
where
A is a phenyl radical or a heteroaromatic radical having 5 or 6 ring atoms, such as pyridyl, pyrazolyl or thienyl, which radicals carry, on one of the two ring atoms next but one to the ring atom to which X is attached, a substituent selected from the group consisting of CH
3
, CH
2
F, CHF
2
, CF
3
, OCH
3
, OCH
2
F, OCHF
2
, OCF
3
and CN, preferably from the group consisting of CH
2
F, CHF
2
, CF
3
, OCH
2
F, OCHF
2
, OCF
3
and CN, and optionally a second substituent selected from the group consisting of halogen, CN, (C
1
-C
8
)-alkyl, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio, for example (C
1
-C
8
)-haloalkyl, (C
1
-C
8
)-haloalkyloxy, (C
1
-C
8
)-haloalkylthio or (C
1
-C
8
)-alkoxy-(C
1
-C
8
)-alkyloxy,
X is O, S or CH
2
,
R
1
is hydroxyl, halogen, CN, NC, CHO or CO(C
1
-C
8
)-alkyl, where the alkyl group is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy, (C
1
-C
8
)-alkylthio, (C
1
-C
8
)-alkylsulfinyl, (C
1
-C
8
)-alkylsulfonyl and [(C
1
-C
8
)-alkoxy]-carbonyl, or CONH
2
, CSNH
2
, nitro, SF
5
, (C
1
-C
8
)-alkyl, (C
2
-C
8
)-alkenyl or (C
2
-C
8
)-alkynyl, where the 3 last-mentioned radicals are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy, (C
1
-C
8
)-alkylthio, (C
1
-C
8
)-alkylsulfinyl, (C
1
-C
8
)-alkylsulfonyl and [(C
1
-C
8
)-alkoxy]carbonyl, or (C
1
-C
8
)-alkoxy, [(C
1
-C
8
)-alkyl]carbonyl or (C
1
-C
8
)-alkylsulfonyl, where the radicals are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio, or
S(O)
p
—R
3
, where
p=0, 1 or 2 and
R
3
is (C
1
-C
8
)-alkyl, (C
1
-C
8
)-haloalkyl or NR
4
R
5
, where R
4
,R
5
independently of one another are identical or different radicals H, (C
1
-C
8
)-alkyl, (C
2
-C
8
)-alkenyl, (C
7
-C
10
)-arylalkyl, (C
7
-C
10
)-alkylaryl or (C
6
-C
10
)-aryl, where each of the five last-mentioned radicals is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio,
or is NR
4
R
5
, where R
4
,R
5
independently of one another are identical or different radicals H, (C
1
-C
8
)-alkyl, (C
2
-C
8
)-alkenyl, (C
7
-C
10
)-arylalkyl, (C
7
-C
10
)-alkylaryl or (C
6
-C
10
)-aryl, where each of the five last-mentioned radicals is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio,
or R
1
is a group of the formula
where R
6
is (C
1
-C
8
)-alkyl, which is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio, and
Z=O or S, and
Z
1
=O or S,
R
2
are identical or different radicals H, halogen, CN or (C
1
-C
8
)-alkyl, which are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio,
Y is O—(CR
8
R
9
)
q
, S(O)
q
, NH, CO(CR
8
R
9
)
q
or CR
8
R
9
and, if B is an unsubstituted or substituted aryl radical, an unsubstituted or substituted heterocyclyl radical, halogen or CN, Y may also be a bond,
where R
8
and R
9
are identical or different radicals H, hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy or (C
1
-C
8
)-alkyl, where each of the two last-mentioned radicals is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio, and
q=0, 1 or 2, and
B is an unsubstituted or substituted aryl radical, for example an unsubstituted or substituted phenyl radical, or an unsubstituted or substituted heterocyclic radical, for example an unsubstituted or substituted heteroaromatic radical, such as unsubstituted or substituted pyridyl, pyrazolyl or thienyl,
H, OH, halogen, CN, nitro, SF
5
, (C
1
-C
8
)-alkyl, (C
2
-C
8
)-alkenyl or (C
2
-C
8
)-alkynyl, where the 3 last-mentioned radicals are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy, (C
1
-C
8
)-alkylthio, (C
1
-C
8
)-alkylsulfinyl, (C
1
-C
8
)-alkylsulfonyl, [(C
1
-C
8
)-alkoxy]-carbonyl, (C
1
-C
8
)-haloalkoxy, (C
1
-C
8
)-haloalkylthio and (C
1
-C
8
)-alkoxy-(C
1
-C
8
)-alkoxy, or
an acyl radical, for example [(C
1
-C
8
)-alkyl]carbonyl, such as straight-chain or branched [(C
1
-C
8
)-alkyl]carbonyl or [(C
3
-C
6
)-cycloalkyl]carbonyl, (C
6
-C
14
)-arylcarbonyl, (C
1
-C
8
)-alkylsulfonyl or (C
6
-C
14
)-arylsulfonyl, where each of the radicals mentioned is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, (C
1
-C
8
)-alkoxy, (C
1
-C
8
)-alkylthio, (C
1
-C
8
)-alkylsulfinyl, (C
1
-C
8
)-alkylsulfonyl, [(C
1
-C
8
)-alkoxy]carbonyl, (C
1
-C
8
)-haloalkoxy, (C
1
-C
8
)-haloalkylthio and CN, or
NR
11
R
12
, where
R
11
,R
12
independently of one another are identical or different radicals H, (C
1
-C
8
)-alkyl, (C
2
-C
8
)-alkenyl, (C
7
-C
10
)-arylalkyl, (C
7
-C
10
)-alkylaryl, (C
6
-C
10
)-aryl or heteroaryl, where each of the six last-mentioned radicals is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio, or an acyl radical, for example [(C
1
-C
8
)-alkyl]carbonyl, such as straight-chain or branched [(C
1
-C
8
)-alkyl]-carbonyl or [(C
3
-C
6
)-cycloalkyl]carbonyl, (C
6
-C
14
)-arylcarbonyl, (C
6
-C
14
)-aryl-(C
1
-C
8
)-alkylcarbonyl, (C
1
-C
8
)-alkylsulfonyl or (C
6
-C
14
)-arylsulfonyl, where each of the radicals mentioned is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, (C
1
-C
8
)-alkoxy, (C
1
-C
8
)-alkylthio, (C
1
-C
8
)-alkylsulfinyl, (C
1
-C
8
)-alkylsulfonyl, [(C
1
-C
8
)-alkoxy]carbonyl, (C
1
-C
8
)-haloalkoxy, (C
1
-C
8
)-haloalkylthio and CN, or
B is a group of the formula
where R
13
is (C
1
-C
8
)-alkyl, which is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio,
R
14
is (C
1
-C
8
)-alkyl, which is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of hydroxyl, halogen, CN, (C
1
-C
8
)-alkoxy and (C
1
-C
8
)-alkylthio,
or R
13
and R
14
together form a ring,
Q=O or S, and
Q
1
=O or S.
In the formula (I) and hereinbelow, the carbon-containing radicals, such as alkyl, alkoxy, haloalkyl, alkylamino and alkylthio radicals, and the corresponding unsaturated and/or substituted radicals, can in each case be straight-chain or branched in

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