Heterocyclically substituted aromatic amino compounds with a...

Details Heterocyclically substituted aromatic amino compounds with a... Heterocyclically substituted aromatic amino compounds with a...

1999-09-20

2003-08-05

Morris, Patricia L. (Department: 1622)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S311000, C544S312000

Reexamination Certificate

active

06602826

ABSTRACT:

This application is a 317 of PCT/EP98/00972 filed Feb. 20, 1998.
TECHNICAL FIELD OF THE INVENTION
The invention relates to new substituted aromatic amino compounds, the processes for their preparation, and to their use as herbicides.
BACKGROUND OF THE INVENTION
Some substituted aromatic amino compounds such as, for example, N-[2-(1,5-dihydro-1-methyl-5-thioxo-3-trifluoromethyl-4H-1,2,4-triazol-4-yl)-5-fluorophen-yl]-benzamide and N-[5-chloro-2-(1,5-dihydro-1-methyl-5-thioxo-3-trifluoromethyl-4H-1,2,4-triazol-4-yl)-phenyl]-acetamide have already been disclosed in the patent literature as candidate herbicides (cf. U.S. Pat. No. 5,108,486). However, these compounds have not gained any particular importance.
Other substituted aromatic amino compounds such as, for example, N-[5-chloro-2-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-acetamide (cf. Indian J. Chem, Sect. B, 29B (1990), 659-660—cited in Chem. Abstracts 113:211906) and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-2,2-dimethyl-propanamide and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-acetamide (cf. JP 02091062—cited in Chem. Abstracts 113:97612) are also known already. However, nothing has been disclosed about the herbicidal activity of these compounds.
DETAILED DESCRIPTION OF THE INVENTION
There have now been found new substituted aromatic amino compounds of the general formula (I)
in which
R
1
represents hydrogen, hydroxyl, amino, alkyl, alkoxy, alkylamino or dialkylamino, or represents one of the groups which follow,
—CQ
1
—R
5
, —CQ
1
—Q
2
—R
6
, —S(O)
n
—R
7
,
R
2
represents one of the groups which follow,
—CQ
1
—R
5
, —CQ
1
—Q
2
—R
6
, —S(O)
n
—R
7
,
R
3
represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, or one of the groups which follow,
—SO
2
—NH—R
5
, —NH—SO
2
—R
7
, —N(SO
2
—R
7
)
2
, —N(SO
2
—R
7
)(CO—R
5
),
R
4
represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, or one of the groups which follow,
—SO
2
—NH—R
5
, —NH-SO
2
—R
7
, —N(SO
2
—R
7
)
2
, —N(SO
2
—R
7
)(CO—R
5
),
n represents the numbers 0, 1 or 2,
Q
1
represents O or S and
Q
2
represents O, S, NH or N-alkyl,
R
5
represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl,
R
6
represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R
7
represents in each case optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heterocyclyl, and
Z represents one of the heterocyclic groups which follow
 where in each case
Q
1
and Q
2
have the abovementioned meaning,
R
8
represents hydrogen, amino, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxycarbonyl, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylamino, dialkylamino, cycloalkyl or cycloalkylalkyl, and
R
9
represents hydrogen, hydroxyl, amino, cyano, or in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, phenyl or phenylalkyl,
where, if appropriate, two adjacent radicals—R
8
and R
8
, R
9
and R
9
or R
8
and R
9
—together represent alkanediyl (alkylene) or oxaalkanediyl, and
where the individual radicals R
8
and R
9
—if they occur more than once in the same heterocyclic group, may have identical or different meanings within the scope of the above definition,
with the exception of the prior-art compound N-[5-chloro-2-(2,5-dihydro-3,4-dimethyl-2,5-dioxo-1H-pyrrol-1-yl)-phenyl]-acetamide (cf. Indian J. Chem, Sect. B, 29B (1990), 659-660—cited in Chem. Abstracts 113:211906), and of N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-pheny]-2,2-dimethyl-propanamide and N-[2-(5-diethylamino-3-t-butyl-1H-1,2,4-triazol-1-yl)-5-trifluoromethyl-phenyl]-acetamide (cf. JP 02091062—cited in Chem. Abstracts 113:97612), which are also prior-art compounds.
The new substituted aromatic amino compounds of the general formula (I) are obtained when aromatic amino compounds of the general formula (II)
in which
R
3
, R
4
and Z have the abovementioned meaning and
A
1
represents hydrogen, hydroxyl, amino, alkyl, alkoxy, alkylamino or dialkylamino
are reacted with electrophilic compounds of the general formula (III)
X—R
2
  (III)
in which
R
2
has the abovementioned meaning and
X represents halogen,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
and the resulting compounds of the general formula (I) are converted into other compounds of the general formula (I) in accordance with the above definition (cf. the preparation examples), if appropriate by customary methods.
The new substituted aromatic amino compounds of the general formula are distinguished by a potent and selective herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl—also in connection with hetero atoms, such as in alkoxy, alkylthio or alkylamino—are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formula (I)
in which
R
1
represents hydrogen, hydroxyl, amino, or represents alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl groups, or represents one of the groups which follow,
 —CQ
1
—R
5
, —CQ
1
—Q
2
—R
6
, —S(O)
n
—R
7
,
R
2
represents one of the groups which follow,
—CQ
1
—R
5
, —CQ
1
—Q
2
—R
6
, —S(O)
n
—R
7
,
R
3
represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, or represents alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkoxy, or represents one of the groups which follow,
—SO
2
—NH—R
5
, —NH—SO
2
—R
7
, —N(SO
2
—R
7
)
2
, —N(SO
2
—R
7
)(CO—R
5
),
R
4
represents hydrogen, hydroxyl, amino, carboxyl, cyano, carbamoyl, thiocarbamoyl, nitro, halogen, or represents alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and each of which is optionally substitued by cyano, halogen or C
1
-C
4
-alkoxy, or represents one of the groups which follow,
—SO
2
—NH—R
5
, —NH—SO
2
—R
7
, —N(SO
2
—R
7
)
2
, —N(SO
2
—R
7
)(CO—R
5
),
n represents the numbers 0, 1 or 2,
Q
1
represents O or S and
Q
2
represents O, S, NH or N-alkyl having 1 to 4 carbon atoms,
R
5
represents hydrogen, or represents alkyl which has 1 to 6 carbon atoms and which is optionally substituted by cyano, halogen or C
1
-C
4
-alkoxy, or represents cycloalkyl or cycloalkylalkyl, each of which has 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, halogen or C
1
-C
4
-alkyl, or represents aryl or arylalkyl, each of which has 6 or 10 carbon atoms in the aryl group and, where appropriate, 1 to 4 carbon atoms in the alkyl moiety and each of which is optionally substituted by cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy or C
1-C
4
-halogenoalkoxy, or represents heterocyclyl which is optionally substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-halogenoalkoxy, preferred heterocyclyl groups being furyl, tetrahydrofuryl, thienyl, pyridyl and pyri

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