Phenylsulfonylureas, processes for their preparation, and...

Details Phenylsulfonylureas, processes for their preparation, and... Phenylsulfonylureas, processes for their preparation, and...

1999-02-01

2001-05-29

McKane, Joseph K. (Department: 1613)

Organic compounds -- part of the class 532-570 series

Organic compounds

Esters having the thiocarboxylate group, -cx-, wherein the...

C558S252000, C558S253000, C558S255000, C560S012000, C560S070000, C562S026000, C564S162000

Reexamination Certificate

active

06239306

ABSTRACT:

It is known that some phenyl sulfonylureas possess herbicidal and plant growth-regulating properties; cf. U.S. Pat. No. 4,786,314, U.S. Pat. No. 4,927,453 and WO 89/10921. However in some cases these phenylsulfonylureas have disadvantages in use, for example a high persistence or inadequate selectivity in important crops.
Phenylsulfonylureas having specific radicals on the phenyl ring have now been found which can be employed advantageously as herbicides and plant growth regulators.
The present invention relates to compounds of the formula (I) or their salts,
in which
R
1
is CO—Q—R
8
,
R
2
and R
3
independently of one another are H or (C
1
-C
4
)alkyl,
R
4
is H, (C
1
-C
8
)alkyl which is unsubstituted or is substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylsulfonyl, [(C
1
-C
4
)alkoxy]carbonyl and CN, or is (C
3
-C
6
)alkyenyl which is unsubstituted or is substituted by one or more halogen atoms, or is (C
3
-C
6
)alkynyl which is unsubstituted or is substituted by one or more halogen atoms, or is hydroxyl, (C
1
-C
4
)alkoxy, [(C
1
-C
4
)alkyl]carbonyl or (C
1
-C
4
)alkylsulfonyl, each of the three latter radicals being unsubstituted or substituted in the alkyl moiety by one or more halogen atoms or by (C
1
-C
4
)alkyoxy or (C
1
-C
4
)alkylthio, or is phenylsulfonyl in which the phenyl radical is unsubstituted or substituted, preferably by one or more radicals from the group consisting of halogen, CN, NO
2
, (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl and (C
1
-C
4
)alkoxy, and
R
5
is (C
1
-C
4
)alkylsuflonyl or (C
3
-C
6
)alkenylsulfonyl, each of the two latter radicals being unsubstituted or substituted by one or more halogen atoms or by (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkylthio, or is phenylsulfonyl or phenylcarbonyl, the phenyl radical in each of the two latter radicals being unsubstituted or substituted, preferably by one or more radicals from the group consisting of halogen, CN, NO
2
, (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl, and (C
1
-C
4
)alkoxy, or is mono- or di-[(C
1
-C
4
)alkyl]aminosulfonyl or [(C
1
-C
6
)alkyl]carbonyl, each of the three latter radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylsulfonyl, [(C
1
-C
4
)alkyl]carbonyl, [(C
1
-C
4
)alkoxy]carbonyl and CN, or is formyl, a group of the formula —CO—CO—R′ in which R′=H, OH, (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkyl, or is [(C
3
-C
6
)cycloalkyl]carbonyl, [(C
2
-C
6
)alkenyl]carbonyl or [(C
2
-C
6
)alkynyl]carbonyl, each of the three latter radicals being unsubstituted or substituted by one or more halogen atoms, or is a group of the formula
or
R
4
and R
5
together are a chain of the formula (—CH
2
)
m
B— or —B
1
—(CH
2
)
m1
—B—, the chain being unsubstituted or substituted by one or more, preferably up to four, (C
1
-C
3
)alkyl radicals and m being 3 or 4 or m
1
being 2 or 3, and
W is an oxygen or sulfur atom (i.e. O or S),
B and B
1
independently of one another are SO
2
or CO,
Q is O, S or —NR
13
—,
T is O or S,
R
6
is H, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, [(C
1
-C
4
)alkyl]carbonyl or [(C
1
-C
4
)alkoxy]carbonyl, each of the 4 latter radicals being unsubstituted or substituted in the alkyl moiety by one or more halogen atoms, or is halogen, NO
2
or CN,
R
7
is H or CH
3
,
R
8
is H, (C
1
-C
4
)alkyl, (C
3
-C
4
)alkenyl or (C
3
-C
4
)alkynyl, each of the three latter radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, [(C
1
-C
4
)alkyl]carbonyl and [(C
1
-C
4
)alkoxy]carbonyl,
R
9
is (C
1
-C
4
)alkyl, (C
3
-C
4
)alkenyl or (C
3
-C
4
)alkynyl, each of the three latter radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, [(C
1
-C
4
)alkyl]carbonyl and [(C
1
-C
4
)alkoxy]carbonyl,
R
10
and R
11
independently of one another are H, (C
1
-C
4
) alkyl, (C
3
-C
4
)alkenyl or (C
3
-C
4
)alkynyl, each of the three latter radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, [(C
1
-C
4
)alkyl]carbonyl and [(C
1
-C
4
)alkoxy]carbonyl,
the radicals R
12
together with the nitrogen atom are a heterocyclic ring having 5 or 6 ring members, which may contain further heteroatoms from the group consisting of N, O and S in the possible oxidation states and is unsubstituted or is substituted by (C
1
-C
4
)alkyl or the oxo group, or is benzo-fused,
R
13
is H, (C
1
-C
4
)alkyl, (C
3
-C
4
)alkenyl or (C
3
-C
4
)alkynyl, each of the three latter radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio,
A is a radical of the formula
one of the radicals X and Y is hydrogen, halogen, (C
1
-C
3
)alkyl or (C
1
-C
3
)alkoxy, the two latter radicals being unsubstituted or being mono- or polysubstituted by halogen or monosubstituted by (C
1
-C
3
)alkoxy, and
the other of the radicals X and Y is hydrogen, (C
1
-C
3
)alkyl, (C
1
-C
3
)alkoxy or (C
1
-C
3
)alkylthio, the three latter alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono- or distributed by (C
1
-C
3
)alkoxy or (C
1
-C
3
)alkylthio, or is a radical of the formula NR
14
R
15
, (C
3
-C
6
)cycloalkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
3
-C
4
)alkenyloxy or (C
3
-C
4
)alkynyloxy,
Z is CH or N,
R
14
and R
15
independently of one another are H, (C
1
-C
3
) alkyl or (C
3
-C
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.
In the formula (I) and below, alkyl, alkoxy, haloalkyl, alkylamino and alkylthio radicals as well as the corresponding unsaturated and/or substituted radicals in the carbon framework may in each case be straight-chain or branched. Alkyl radicals, alone or in composite definitions such as alkoxy, haloalkyl etc., are methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl; alkenyl and 2alkynyl radicals have the definition of the possible unsaturated radicals corresponding to the alkyl radicals, such as 2-propenyl, 2- or 3-butenyl, 2-propynyl, or 2- or 3-butynyl. Halogen is fluorine, chlorine, bromine or iodine; haloalkyl is alkyl which is substituted by one or more atoms from the group consisting of halogen; examples of haloalkyl are CF
3
, CHF
2
and CH
2
CF
3
. Substituted phenyl is advantageously phenyl which is substituted by one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, such as F, Cl, Br and I, preferably F, Cl and Br, and also alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyl, amino, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and dialkylamino, alkylsulfinyl and alkylsulfonyl, and, for radicals containing carbon atoms, those having from 1 to 4 carbon atoms, especially 1 to 2, are preferred. In this context preference is generally given to substituents from the group consisting of halogen, for example fluorine and chlorine, C
1
-C
4
-alkyl, preferably methyl or ethyl, C
1
-C
4
-haloalkyl, preferably trifluoromethyl, C
1
-C
4
-alkoxy, preferably methoxy or ethoxy, C
1
-C
4
-haloalkoxy, nitro and cyano.
A 5- or 6-membered heterocyclic radical which may if desired be benzo-fused and which contains a nitrogen atom (e.g. in the case of N(R
12
)
2
) may be a saturated, unsaturated or heteroaroamtic radical, for exampl

Affiliated with

Also associated with

Rating

Phenylsulfonylureas, processes for their preparation, and... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Phenylsulfonylureas, processes for their preparation, and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenylsulfonylureas, processes for their preparation, and... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2521506