Substituted aniline compounds

Details Substituted aniline compounds Substituted aniline compounds

2001-09-11

2004-01-27

Kumar, Shailendra (Department: 1621)

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

Organic compounds

Amino nitrogen containing

C558S411000, C558S418000, C558S425000, C560S043000

Reexamination Certificate

active

06683213

ABSTRACT:

The present invention relates to polysubstituted aniline compounds and to their use for the production of novel, herbicidally active compounds.
2-Aminobenzaldehyde O-methyloxime is known from Synthesis 1984, 266; it was prepared according to the methods described in Chem. Ber. 83, 78 (1950) and 34, 1330 (1901) and used for the synthesis of dihydroquinolinecarboxylic acid derivatives.
DE 1 231 709 shows a process for the preparation of o-aminobenzonitriles by thermolysis of &bgr;-isatin oximes. For example, 5-chloro- and 5-methyl-2-aminobenzonitrile are described, which can be used as intermediates for dyes, pesticides and therapeutics.
EP 32 672 A describes a process for the preparation of anthranilic acid esters by reaction of isatins with alcohols in the presence of hydrogen peroxide and alkali metal alkoxides. For example, the synthesis of methyl 3,5-dichloroanthranilate is discussed.
2,3,6-substituted anilines are described in Chem. Abstr. 73, 3578; 112, 5543; 78, 71690; 118, 147479; 70, 11553; 93, 71617; 121, 255784; 123, 313944; 76, 113245; 79, 146540; 128, 308308 and 131,129760.
The present invention relates to substituted anilines of the formula 1
in which the variables R
21
, R
22
and R
23
have the following meanings:
R
21
is C
1
-C
3
-alkoxymethyl, C
1
-C
3
-alkoximinomethyl, C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C(O)NH
2
, CN, Cl, Br, C
1
-C
3
-alkyl;
R
22
is Cl, Br, C
1
-C
3
-alkyl;
R
23
is hydrogen, C
1
-C
3
-alkoxymethyl, C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C(O)NH
2
, CN, Cl, Br, C
1
-C
3
-alkyl, C
1
-C
3
-alkoxy;
where
at least one of the radicals R
21
or R
23
is a group having a carbonyl group or a functional derivative thereof or is C
1
-C
3
-alkoxymethyl;
R
23
cannot be hydrogen nor can R
22
and R
23
have the same meaning if R
21
=C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C(O)NH
2
or CN;
R
22
does not have the same meaning as R
21
if R
21
is Cl, Br or C
1
-C
3
-alkyl and R
23
is C
1
-C
3
-alkoxycarbonyl and R
22
is not Cl if R
21
is CH
3
and R
23
is C
1
-C
3
-alkoxycarbonyl,
if R
21
=C
1
-C
3
-alkoxymethyl, R
23
is not hydrogen;
and the salts thereof.
Suitable salts are those with inorganic or organic acids. Suitable inorganic acids are, for example, hydrochloric acid, sulfuric acid, phosphoric acid, nitric acid etc. Suitable organic acids are, for example, acetic acid, citric acid, tartaric acid etc.
The organic moieties mentioned in the definition of R
21
, R
22
and R
23
are collective terms for individual lists of the individual group members. All carbon chains, i.e. all alkyl moieties, can be straight-chain or branched.
The following are, for example:
C
1
-C
3
-alkoxymethyl: methoxymethyl, ethoxyethyl, n-propoxymethyl or 2-propoxymethyl, in particular 2-methoxymethyl;
C
1
-C
3
-alkoximinomethyl: methoximinomethyl, ethoximinomethyl, n-propoximinomethyl or 2-Propoximinomethyl, in particular methoximinomethyl;
C
1
-C
3
-alkoxycarbonyl: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl or 2-propoxycarbonyl, in particular methoxycarbonyl;
C
1
-C
3
-alkylthiocarbonyl: methylthiocarbonyl, ethylthiocarbonyl, n-propylthiocarbonyl or 2-propylthiocarbonyl, in particular methylthiocarbonyl;
C
1
-C
3
-alkyl: methyl, ethyl, n-propyl or 2-propyl, in particular methyl or ethyl;
C
1
-C
3
alkoxy: methoxy, ethoxy, n-propoxy or 2-propoxy, in particular methoxy or ethoxy.
The groups having a carbonyl group or a functional derivative thereof are C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl (C
1
-C
3
-alkyl-S—CO), C(O)NH
2
, CN and C
1
-C
3
-alkoximinomethyl.
R
21
is preferably methoxymethyl, methoximinomethyl, ethoximinomethyl, methoxycarbonyl, ethoxycarbonyl, methylthiocarbonyl, CN, Cl, Br, methyl or ethyl;
R
22
is preferably Cl, Br, CH
3
or C
2
H
5
;
R
23
is preferably hydrogen, methoxymethyl, methoxycarbonyl, methylthiocarbonyl, CN, Cl, Br, methyl, ethyl, methoxy or ethoxy.
Preferred compounds of the formula 1 are those in which the variables have the following meanings:
A) R
21
is C
1
-C
3
-alkoxymethyl, C
1
-C
3
-alkoximinomethyl, C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C(O)NH
2
, Cl, Br, CN or C
1
-C
3
-alkyl;
R
22
is Cl, Br or C
1
-C
3
-alkyl and
R
23
is C
1
-C
3
-alkoxymethyl.
B) R
21
is C
1
-C
3
-alkoxymethyl or C
1
-C
3
-alkoximinomethyl;
R
22
is Cl, Br or C
1
-C
3
-alkyl and
R
23
is H, C
1
-C
3
-alkoxymethyl, C
1
-C
3
-alkylcarbonyl, C
1
-C
3
-alkylthiocarbonyl, C(O)NH
2
, Cl, Br, C
1
-C
3
-alkyl or C
1
-C
3
-alkoxy, where R
23
cannot be H if R
21
is C
1
-C
3
-alkoxymethyl.
C) R
21
is C
1
-C
3
-alkoximinomethyl;
R
22
is Cl or Br;
R
23
is hydrogen, C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkoxy, C(O)NH
2
, or cyano.
D) R
21
is C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C(O)NH
2
or cyano;
R
22
and R
23
, which are different from one another, are Cl, Br or C
1
-C
3
-alkyl, R
23
is furthermore C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl or C
1
-C
3
-alkoxy.
E) R
21
and R
22
are Cl, Br or C
1
-C
3
-alkyl
R
23
is C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, C
1
-C
3
-alkoxymethyl or cyano, where in the two first-mentioned cases R
21
and R
22
do not have the same meanings.
F) R
21
is C
1
-C
3
-alkoxymethyl or C
1
-C
3
-alkoximinomethyl
R
22
is Cl, Br or C
1
-C
3
-alkyl
R
23
is C
1
-C
3
-alkoxycarbonyl, C
1
-C
3
-alkylthiocarbonyl, CN, C
1
-C
3
-alkyl or C
1
-C
3
-alkoxy.
The compounds of the formula 1 are intermediates for the preparation of the herbicidally active compounds of the formula A
in which R
21
, R
22
and R
23
have the meanings indicated above,
R
1
is halogen, CN, NO
2
, C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-alkoxy, C
1
-C
3
-haloalkoxy, C
1
-C
3
-alkylthio, C
1
-C
3
-haloalkylthio, C
1
-C
3
-alkylsulfinyl, C
1
-C
3
-haloalkylsulfinyl, C
1
-C
3
-alkylsulfonyl, C
1
-C
3
-haloalkylsulfonyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyl-C
1
-C
3
-alkyl, C
2
-C
4
-alkenyl, C
2
-C
4
-haloalkenyl, C
2
-C
4
-alkynyl, C
3
-C
4
-haloalkynyl, amino, C
1
-C
3
-monoalkylamino or C
1
-C
3
-alkylcarbonyl;
R
5
is hydrogen, C
1
-C
3
-alkyl, OH or C
1
-C
4
-alkoxy;
R
6
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-cyanoalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkenyl, C
3
-C
6
-cycloalkyl-C
1
-C
3
-alkyl, C
3
-C
6
-cycloalkyl which has 1 or 2 substituents which independently of one another are selected from halogen or C
1
-C
3
-alkyl, C
3
-C
6
-cycloalkoxy-C
1
-C
3
-alkyl, C
1
-C
6
-Alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, amino, C
1
-C
4
-monoalkylamino, di-C
1
-C
4
-alkylamino or R
6
, together with R
5
, is a 5- or 6-membered heterocycle which has 1, 2 or 3 heteroatoms, which independently of one another are selected from N, O and S, and optionally 1 or 2 substituents which independently of one another are selected from halogen or C
1
-C
3
-alkyl, C
1
-C
3
-alkoxy or C
1
-C
3
-haloalkyl;
m is 0 or 1 and n is 0, 1, 2 or 3. The compounds of the formula A are the subject of DE 199 14 721 of 31.3.1999.
Examples of preferred substituted anilines of the formula 1 are indicated in Table 1, in which R
21
to R
23
have the following meanings:
No.
R
21
R
22
R
23
1
CH═NOCH
3
Cl
H
2
CH═NOCH
3
Br
H
3
CH═NOCH
3
CH
3
H
4
CH═NOCH
3
C
2
H
5
H
5
CH═NOCH
3
Cl
CO
2
CH
3
6
CH═NOCH
3
Br
CO
2
CH
3
7
CH═NOCH
3
CH
3
CO
2
CH
3
8
CH═NOCH
3
Cl
CN
9
CH═NOCH
3
Br
CN
10
CH═NOCH
3
Cl
Cl
11
CH═NOCH
3
Cl
Br
12
CH═NOCH
3
Br
Cl
13
CH═NOCH
3
Cl
C(O)NH
2
14
CH═NOCH
3
Cl
CH
3
15
CH═NOCH
3
Br
CH
3
16
CH═NOCH
3
CH
3
CN
17
CH═NOCH
3
CH
3
Cl
18
CH═NOCH
3
Cl
CH
3
O
19
CH═NOCH
3
Br
CH
3
O
20
CH═NOCH
3
Cl
C(O)SCH
3
21
CH═NOCH
3
Br
C(O)SCH
3
22
CH═NOCH
3
Cl
C
2
H
5
23
CH═NOCH
3
Br
C
2
H
5
24
CH═NOC
2
H
5
Cl
H
25
CH═NOC
2
H
5
Br
H
26
CH═NOC
2
H
5
CH
3
H
27
CH═NOC
2
H
5
C
2
H
5
H
28
CH═NOC
2
H
5
Cl
CO
2
CH
3
29
CH═NOC
2
H
5
Br
CO
2
CH
3
30
CH═NOC
2
H
5
CH
3
CO
2
CH
3
31
CH═NOC

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