Substituted sulfonylaminomethylbenzoic acid (derivatives)...

Details Substituted sulfonylaminomethylbenzoic acid (derivatives)... Substituted sulfonylaminomethylbenzoic acid (derivatives)...

2001-07-20

2003-03-25

Rotman, Alan L. (Department: 1625)

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

Organic compounds

Carboxylic acid esters

C560S008000, C560S009000, C560S019000, C560S013000, C562S426000, C562S433000, C562S430000, C504S214000

Reexamination Certificate

active

06538150

ABSTRACT:

The invention relates to the technical field of the intermediates for the preparation of active substances, in particular herbicidally active sulfonylureas.
It is known that aromatic amines can be reacted to give sulfonic acid derivatives such as sulfochlorides and further to give sulfonamides which, in turn, can be employed for the preparation of herbicidally active sulfonylureas (Meerwein et al., Chem. Berichte 90, 841-852 (1957) and EP-A-574418).
A substituted anthranilic acid is known from J. Med. Chem. 1986, Vol. 29, No. 4, page 585 as intermediate for the preparation of certain anhydrides which are suitable for inactivating trypsin-like enzymes.
It was an object to provide novel chemical compounds which are suitable for the preparation of herbicidally active sulfonylureas. Surprisingly, this object is achieved by compounds of the formula (I)
in which
R
1
is H, (C
1
-C
8
)alkyl, (C
3
-C
8
)alkenyl or (C
3
-C
8
)alkynyl, where the last 3 radicals are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, [(C
1
-C
4
)alkyl]carbonyl or [(C
1
-C
4
)alkoxy]carbonyl,
R
2
, R
3
independently of one another are H or acyl, preferably H,
R
4
, R
5
are H,
R
6
is H or (C
1
-C
8
)alkyl which is unsubstituted or substituted, for example by one or more radicals selected 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 or CN, preferably H,
R
7
is (C
1
-C
8
)alkyl, (C
3
-C
8
)alkenyl or (C
3
-C
8
)alkynyl which are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkylthio, or R
7
is (C
6
-C
14
)aryl (for example phenyl) which is unsubstituted or substituted, for example by one or more radicals selected from the group consisting of halogen, NO
2
, CN, (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl or (C
1
-C
4
)alkoxy, or R
7
is mono- or di-(C
1
-C
8
)alkylamino which is unsubstituted or substituted, for example by one or more radicals selected 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 or CN, or
R
6
and R
7
together form a chain of the formula —(CH
2
)
m
B
m
1
— which is unsubstituted or substituted, for example by one or more (C
1
-C
4
)alkyl radicals, and where m=2, 3 or 4, m
1
=0 or 1 and B═CO or SO
2
,
R
8
radicals, are identical or different and are (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, [(C
1
-C
4
)alkyl]carbonyl or [(C
1
-C
4
)alkoxy]carbonyl which are unsubstituted or substituted, for example by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, [(C
1
-C
4
)alkyl]carbonyl or [(C
1
-C
4
)alkoxy]carbonyl, or R
8
is halogen or NH
2
, and
n is 0, 1, 2 or 3, preferably 0.
Preferred compounds of the formula (I) are those in which
R
1
is H or (C
1
-C
4
)alkyl, preferably (C
1
-C
4
)alkyl,
R
2
and R
3
are H,
R
4
and R
5
are H,
R
6
is H,
R
7
is (C
1
-C
4
)alkyl, and
n is 0.
Compounds of the formula (I) which are of particular importance are those in which the group CR
4
R
5
—NR
6
—SO
2
—R
7
is in the para position relative to the group —CO—OR
1
. If together form a chain of the formula —(CH
2
)
m
B
m1
— and m
1
=1, it is preferable that B is bound to the nitrogen atom which has R
6
attached to it.
Examples of compounds of the formula (I) are listed in table 1 hereinbelow:
TABLE 1
(Ia)

Compound
R
1
R
6
R
7
1
Me
H
Me
2
Me
Me
Me
3
Me
H
NHMe
4
Me
Me
NHMe
5
Me
H
N(Me)
2
6
Me
Me
N(Me)
2
7
Me
—CH
2
—CH
2
—CH
2
—
8
Me
—CH
2
—CH
2
—CH
2
—CH
2
—
9
Me
H
Phe
10
Me
Me
Phe
11
Me
H
CH
2
F
12
Me
Me
CH
2
F
13
Me
H
CF
3
14
Me
Me
CF
3
15
Me
H
Et
16
Me
Me
Et
17
Me
H
nPr
18
Me
Me
nPr
19
Me
H
iPr
20
Me
Me
iPr
21
Me
H
nBu
22
Me
Me
nBu
23
Me
Et
Me
24
Me
Et
Et
25
Me
Et
NHMe
26
Me
Et
N(Me)
2
27
Me
Et
Phe
28
Me
Et
CH
2
F
29
Me
Et
CF
3
30
Me
Et
nPr
31
Me
Et
iPr
32
Me
Et
nBu
33
Et
H
Me
34
Et
Me
Me
35
Et
H
NHMe
36
Et
Me
NHMe
37
Et
H
N(Me)
2
38
Et
Me
N(Me)
2
39
Et
—CH
2
—CH
2
—CH
2
—
40
Et
—CH
2
—CH
2
—CH
2
—CH
2
—
41
Et
H
Phe
42
Et
Me
Phe
43
Et
H
CH
2
F
44
Et
Me
CH
2
F
45
Et
H
CF
3
46
Et
Me
CF
3
47
Et
H
Et
48
Et
Me
Et
49
Et
H
nPr
50
Et
Me
nPr
51
Et
H
iPr
52
Et
Me
iPr
53
Et
H
nBu
54
Et
Me
nBu
55
Et
Et
Me
56
Et
Et
Et
57
Et
Et
NHMe
58
Et
Et
N(Me)
2
59
Et
Et
Phe
60
Et
Et
CH
2
F
61
Et
Et
CF
3
62
Et
Et
nPr
63
Et
Et
iPr
64
Et
Et
nBu
In table 1, Me = methyl, Et = ethyl, nPr = n-propyl, iPr = isopropyl, nBu = n-butyl, Phe = phenyl.
If the term acyl is used in the present description, it denotes the radical of an organic acid which arises formally by eliminating an OH group from the organic acid, for example the radical of a carboxylic acid and radicals of acids derived therefrom, such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radicals of carbonic monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids, phosphinic acids.
An acyl radical is preferably formyl or acyl from the group consisting of CO—R
x
, CS—R
x
, CO—OR
x
, CS—OR
x
, CS—SR
x
, Cr
x
═NR
Y
, SOR
Y
or SO
2
Y
, where R
x
and R
Y
are each a C
1
-C
10
-hydrocarbon radical such as C
1
-C
10
-alkyl or C
6
-C
10
-aryl, each of which is unsubstituted or substituted, for example by one or more substituents selected from the group consisting of halogen such as F, Cl, Br, I, alkoxy, haloalkoxy, hydroxyl, amino, nitro, cyano or alkylthio, or acyl is aminocarbonyl or aminosulfonyl, the two last-mentioned radicals being unsubstituted, N-monosubstituted or N,N-disubstituted, for example by substituents from the group consisting of alkyl or aryl. Acyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl such as (C
1
-C
4
)alkylcarbonyl, phenylcarbonyl, it being possible for the phenyl ring to be substituted, or alkyloxycarbonyl, such as (C
1
-C
4
) alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, such as (C
1
-C
4
) alkylsulfonyl, alkylsulfinyl, such as C
1
-C
4
(alkylsulfinyl), N-alkyl-1-iminoalkyl, such as N—(C
1
-C
4
)-1-imino-(C
1
-C
4
)alkyl and other radicals of organic acids.
In formula (I) and the general formulae used hereinbelow, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy and alkylthio and the corresponding substituted radicals can be in each case straight-chain or branched in the carbon skeleton. Unless specified otherwise, the lower carbon skeletons, for example those having 1 to 4 carbon atoms, are preferred amongst these radicals. Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyls, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meanings of the possible unsaturated radicals which correspond to the alkyl radicals; for example alkenyl is allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.
Alkenyl, for example in the form “(C
3
-C
8
)alkenyl”, is preferably an alkenyl radical having 3 to 8 carbon atoms in which the double bond is not positioned at the carbon atom which is linked to the remaining moiety of the compound (I) (“yl” position). This also applies analogously to alkynyl radicals.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl, each of which is partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF
3
, CHF
2
, CH
2
F, C

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