Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1998-01-21
2002-06-25
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C504S214000, C544S122000, C544S123000, C544S295000, C544S296000, C544S321000
Reexamination Certificate
active
06410483
ABSTRACT:
It is known that some phenylsulfonylureas have herbidical and plant-growth-regulating properties; cf. U.S. Pat. No. 4,786,314, U.S. Pat. No. 4,927,453, WO 89/10921 and WO 95/10507 (=ZA 94/8063). However, some of these show disadvantages upon use, such as, for example, high persistence or insufficient selectivity in important crops of useful plants.
There have now been found novel phenylsulfonylureas which have specific radicals on the phenyl ring and which can be employed advantageously as herbicides and plant growth regulators.
The present invention relates to compounds of the formula (I) or salts thereof
in which
R
1
is an acyl radical of the formula S(O)
n
—R
10
or CO—Q—R
11
,
R
2
, R
3
, R
4
, R
5
are identical or different radicals selected from the group consisting of H, (1-6)alkyl, (1-4)alkoxy, (1-4)haloalkyl, (1-4)haloalkoxy and halogen,
R
6
is H, OH, formyl, a radical of the formula R, R—O—, R—CO, R—O—CO—, R—SO
2
—, R—SO— or RR
0
NSO
2
—, in which each of the radicals R and R
0
is a hydrocarbon radical which is unsubstituted or substituted and, inclusive of substituents, preferably has 1 to 20 carbon atoms,
R
7
is an acyl radical or
NR
6
R
7
together are a heterocyclic radical which has 2 to 8 ring atoms and which, besides the nitrogen atom of the group NR
6
R
7
as hetero ring atom, optionally has 1 to 3 further hetero ring atoms selected from the group consisting of N, O and S and which is unsubstituted or substituted and, inclusive of substituents, preferably has 2 to 18 carbon atoms and which has at least one electron-attracting group in neighboring position to the nitrogen atom of the group NR
6
R
7
,
W is an oxygen or sulfur atom,
R
8
is H, (1-6)alkyl, (2-6)alkenyl, (1-6)alkoxy, (1-4)alkylthio, [(1-4)alkyl]carbonyl or [(1-4)alkoxy]carbonyl, each of the six last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio and CN, or is halogen, NO
2
, CN, NH
2
or mono- or disubstituted amino,
R
9
is H or (1-6)alkyl,
R
10
is NH
2
, mono- or disubstituted amino or a hydrocarbon radical which is unsubstituted or substituted and which, inclusive of substituents, preferably has 1 to 30 carbon atoms,
n is the number 0, 1 or 2, with the exception of the case R
10
=NH
2
or mono- or disubstituted amino, in which case n=2,
R
11
is H or a hydrocarbon radical which is unsubstituted or substituted and, inclusive of substituents, preferably has 1 to 30 C atoms, or is a heterocycle which has 3 to 8 ring atoms and which is unsubstituted or substituted and, inclusive of substituents, preferably has 1 to 20 carbon atoms,
Q is an oxygen or sulfur atom or a group of the formula —NR′— in which R′ is H or a hydrocarbon radical which is unsubstituted or substituted, or is an acyl radical in which R′ is preferably H or has 1 to 10 carbon atoms,
A is a radical of the formula
one of the radicals X and Y is hydrogen, halogen, (1-3 )alkyl or (1-3)alkoxy, each of the two last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-3)alkoxy and (1-3)alkylthio, and
the other of the radicals X and Y is hydrogen, halogen, (1-3)alkyl, (1-3)alkoxy or (1-3)alkylthio, each of the three last-mentioned alkyl-containing radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-3)alkoxy and (1-3)alkylthio, or is a radical of the formula NR
a
R
b
, (3-6)cycloalkyl, (2-4)alkenyl, (2-4)alkynyl, (3-4)alkenyloxy or (3-4)alkynyloxy,
Z is CH or N,
R
a
and R
b
independently of one another are H, (1-4)alkyl or (2-4)alkenyl,
X
1
is CH
3
, OCH
3
, OC
2
H
5
or OCHF
2
,
Y
1
is —O— or —CH
2
—,
X
2
is CH
3
, C
2
H
5
or CH
2
CF
3
,
Y
2
is OCH
3
, OC
2
H
5
, SCH
3
, SCH
2
CH
3
, CH
3
or C
2
H
5
,
X
3
is CH
3
or OCH
3
,
Y
3
is H or CH
3
,
X
4
is CH
3
, OCH
3
, OC
2
H
5
, CH
2
OCH
3
or Cl,
Y
4
is CH
3
, OCH
3
, OC
2
H
5
or Cl and
Y
5
is CH
3
, C
2
H
5
, OCH
3
or Cl.
Of greater interest are those compounds of the formula (I) according to the invention and salts thereof in which
R
1
is S(O)
n
—R
10
or COQR
11
,
R
2
, R
3
, R
4
, R
5
independently of one another are H or (1-4)alkyl,
R
6
is H, OH, formyl, (1-6)alkyl, (2-6)alkenyl, (2-4)alkynyl, (1-6)alkoxy, (2-6)alkenyloxy, (2-6)alkynyloxy, [(1-6)alkyl]carbonyl, [(2-6)alkenyl]carbonyl, [(2-6)alkynyl]carbonyl), (1-4)alkylsulfonyl, (2-6)alkenylsulfonyl, (2-6)alkynylsulfonyl, (3-6)cycloalkyl, (5-6)cycloalkenyl, [(3-6)cycloalkyl]carbonyl, [(5-6)cycloalkenyl]carbonyl, [(3-6)cycloalkyl]sulfonyl, [(5-6)cycloalkenyl]sulfonyl, each of the 18 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, (1-4)alkylsulfinyl, (1-4)alkylsulfonyl, [(1-4)alkoxy]carbonyl, [(1-4)alkyl]carbonyl, [(1-4)alkyl]carbonyloxy and CN and, in the case of cyclic radicals, also by (1-4)alkyl and (1-4)haloalkyl, or
phenylcarbonyl or phenylsulfonyl, each of the two last-mentioned radicals being unsubstituted or substituted in the phenyl ring by one or more radicals selected from the group consisting of halogen, CN, NO
2
, (1-4)alkyl, (1-4)haloalkyl, (1-4)alkoxy and (1-4)haloalkoxy,
R
7
is CHO, [(1-6)alkyl]carbonyl, [(2-6)alkenyl]carbonyl, [(2-6)alkynyl]carbonyl, (1-6)alkylsulfonyl, (2-6)alkenylsulfonyl, (2-6)alkynylsulfonyl, [(3-6)cycloalkyl]carbonyl, [(5-6)cycloalkenyl]carbonyl, [(3-6)cycloalkyl]sulfonyl, (5-6)cycloalkenylsulfonyl, each of the 10 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, (1-4)alkylsulfonyl, (1-4)alkylsulfinyl, (1-4)alkylcarbonyl, [(1-4)alkoxy]-carbonyl, [(1-4)alkyl]carbonyloxy and CN and, in the case of cyclic radicals, also by (1-4)alkyl and (1-4)haloalkyl, or
phenylcarbonyl or phenylsulfonyl, each of the two last-mentioned radicals being unsubstituted or substituted in the phenyl ring by one or more radicals selected from the group consisting of halogen, CN, NO
2
, (1-4)alkyl, (1-4)haloalkyl, (1-4)alkoxy and (1-4)haloalkoxy, or
mono- or di[(1-4)alkyl]aminosulfonyl which is unsubstituted or substituted in the alkyl moiety by one or more radicals selected from the group consisting of halogen, (1-4)alkoxy, (1-4)alkylthio, (1-4)alkylsulfinyl, (1-4)alkylsulfonyl, [(1-4)alkyl]carbonyl, [(1-4)alkyl]carbonyloxy, [(1-4)alkoxy]carbonyl and CN, or a group of the formula COCOR′ in which R′=H, OH, (1-4)alkoxy or (1-4)alkyl, or a group of the formula
R
6
and R
7
together are a chain of the formula (—CH
2
)
m1
B
1
— or —B
1
—(CH
2
)
m2
B
2
—, the chain being unsubstituted or substituted by one or more (1-3)alkyl radicals or halogen and m1 is 3, 4 or 5 and m2 is 2, 3 or 4, and
W, W
o
are an oxygen atom or a sulfur atom,
B
1
, B
2
independently of one another are SO
2
or CO,
Q is O, S or NR
16
,
T
o
is an oxygen atom or a sulfur atom,
R
8
is H, (1-4)alkyl, (1-4)alkoxy, (1-4)alkylthio, [(1-4)alkyl]carbonyl or [(1-4)alkoxy]carbonyl, each of the last-mentioned 5 radicals being unsubstituted or substituted in the alkyl moiety by one or more halogen atoms, or is halogen, NO
2
, CN or mono- or di(1-4)alkylamino,
R
9
is H or CH
3
,
R
10
is NR
17
R
18
, (1-6)alkyl, (2-6)alkenyl, (2-6)alkynyl, (3-6)cycloalkyl, (5-6)cycloalkenyl or phenyl, each of the last-mentioned 6 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, CN, (1-4)alkoxy, (1-4)alkylthio, (1-4)alkylsulfinyl, (1-4)alkylsulfonyl, [(1-4)alkyl]carbonyl, [(1-4)alkoxy]carbonyl and [(1-4)alkyl]carbonyloxy,
n is the number 0, 1 or 2, unless R
10
=NR
17
R
18
, in which cas
Bauer Klaus
Bieringer Hermann
Lorenz Klaus
Rosinger Christopher
Willms Lothar
Ford John M.
Frommer & Lawrence & Haug LLP
Hoechst Schering AgrEvo GmbH
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