N-P-Cyanoaryl nitrogen-containing heterocycles having...

Details N-P-Cyanoaryl nitrogen-containing heterocycles having... N-P-Cyanoaryl nitrogen-containing heterocycles having...

1998-03-27

2002-01-15

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S243000, C504S219000, C504S221000, C544S285000, C544S238000, C544S311000, C544S312000, C544S253000

Reexamination Certificate

active

06339044

ABSTRACT:

The invention relates to novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings, a plurality of processes for their preparation and their use as herbicides and insecticides.
It is already known that certain N-cyanoaryl nitrogen heterocycles have herbicidal properties (cf. WO-A 91/00278, WO-A 92/11244, EP-A 408382, EP-A 438209, EP-A 473551, DE-A 4237920). However, the herbicidal action and the compatibility of the previously known N-cyanoaryl nitrogen heterocycles with cultivated plants are not entirely satisfactory.
The novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings of the general formula (I) have now been found,
in which
Q
1
represents oxygen or sulphur,
R
1
represents hydrogen or halogen,
R
2
represents halogen, cyano, nitro, amino or the grouping —N(A
1
)SO
2
A, in which
A represents, in each case, optionally substituted alkyl, alkenyl, alkinyl, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, and
A
1
represents hydrogen, formyl or, in each case optionally substituted, alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl, or
together with A represents alkanediyl,
R
3
represents hydrogen, halogen, cyano or optionally substituted alkyl,
R
4
represents optionally substituted alkyl or together with R
3
represents alkanediyl, and
Z represents one of the groupings below
 in which
Q
2
represents oxygen or sulphur and
R
5
represents hydrogen or, in each case optionally substituted, alkyl, alkenyl, alkinyl or alkylcarbonyl,
and salts of compounds of the formula (I)
with the proviso that at least one of the groupings Q
1
or Q
2
represents sulphur.
The general formula (I) therefore represents the isomeric compounds of the general formulae (IA) and (IB) below
The novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings of the general formula (I) are obtained if
(a) aminoalkenoic (thio)esters of the general formula (II)
 in which
Q
1
, R
3
, R
4
and R
5
have the meanings given above and
R represents alkyl,
are reacted with cyanoaryl iso(thio)cyanates of the general formula (III)
 in which
Q
2
, R
1
and R
2
have the meanings given above,
in the presence or absence of a reaction auxiliary and in the presence or absence of a diluent,
or if
(b) for the preparation of compounds of the formulae (IA) and/or (IB) in which R
5
represents, in each case optionally substituted, alky, alkenyl or alkinyl and Q
1
, Q
2
, R
1
, R
2
, R
3
and R
4
have the meanings given above,
N-cyanoaryl nitrogen heterocycles of the general formula (IA) or (IB)
in which R
5
represents hydrogen and Q
1
, Q
2
, R
1
, R
2
, R
3
and R
4
have the meanings given above,
are reacted with alkylating agents of the general formula (IV) or (V)
X—R
5
  (IV)
R
5
—O—SO
2
—O—R
5
  (V)
in which R
5
represents, in each case optionally substituted, alkyl, alkenyl or alkinyl,
in the presence or absence of an acid acceptor and in the presence or absence of a diluent,
or if
(c) for the preparation of compounds of the formula (I) in which R
2
represents amino or the grouping —N(A
1
)SO
2
A and A, A
1
, Q
1
, Q
2
, R
1
, R
3
, R
4
and Z have the meanings given above,
N-cyanoaryl nitrogen heterocycles of the general formula (I), in which R
2
represents halogen and Q
1
, Q
2
, R
1
, R
3
, R
4
and Z have the meanings given above,
are reacted with ammonia or with amides of the general formula (VI)
HN(A
1
)SO
2
A  (VI)
in which
A and A
1
have the meanings given above,
in the presence or absence of an acid acceptor and in the presence or absence of a diluent.
The compounds of the formula (I) can, by analogy with process (a), also be obtained by reaction of aminoalkenoic (thio)esters of the formula (II)—above—with cyanoaryl (thio)urethanes of the formula (IIIa)
in which
Q
2
, R
1
and R
2
have the meanings given above and
R represents alkyl (in particular methyl) or aryl (in particular phenyl).
The novel N-cyanoaryl nitrogen heterocycles having sulphur-containing groupings of the general formula (I) are distinguished by high herbicidal efficiency.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are each 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
Q
1
represents oxygen or sulphur,
R
1
represents hydrogen, fluorine, chlorine or bromine,
R
2
represents fluorine, chlorine, bromine, cyano, nitro, amino or the grouping —N(A
1
)SO
2
A, in which
A represents a radical selected from the group consisting of alkyl, alkenyl, alkinyl or dialkylamino each having up to 10 carbon atoms and each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C
1
-C
4
-alkoxy,
A further represents cycloalkyl or cycloalkylalkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano or C
1
-C
4
-alkyl, having 3 to 8 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety,
A further represents aryl or arylalkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, carboxy, carbamoyl, by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl (which are each optionally substituted by fluorine and/or chlorine), by dimethylaminosulphonyl or diethylaminosulphonyl, by C
1
-C
4
-alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy), by phenyl or phenyloxy (which are each optionally substituted by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy), having 6 or 10 carbon atoms in the aryl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, and
A
1
represents hydrogen or formyl, or C
1
-C
4
-alkyl which is optionally substituted by fluorine and/or chlorine, cyano or C
1
-C
4
-alkoxy-carbonyl, or C
1
-C
4
-alkyl-carbonyl or C
1
-C
4
-alkoxy-carbonyl, each of which is optionally substituted by fluorine, chlorine or C
1
-C
4
-alkoxy, or C
1
-C
4
-alkylsulphonyl which is optionally substituted by fluorine and/or chlorine, or
together with A represents alkanediyl having 2 to 8 carbon atoms,
R
3
represents hydrogen, fluorine, chlorine, bromine, cyano or alkyl, which is optionally substituted by fluorine and/or chlorine, having 1 to 4 carbon atoms,
R
4
represents alkyl, which is optionally substituted by fluorine, chlorine, bromine, methoxy or ethoxy, having 1 to 6 carbon atoms,
or together with R
3
represents alkanediyl having 2 to 8 carbon atoms, and
Z represents one of the groupings below
 in which
Q
2
represents oxygen or sulphur and
R
5
represents hydrogen or alkyl, alkenyl, alkinyl or alkylcarbonyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, C
1
-C
4
-alkoxy, C
1
-C
4
-alkyl-carbonyl or C
1
-C
4
-alkoxy-carbonyl, and each of which has up to 6 carbon atoms,
with the proviso that at least one of the groupings Q
1
or Q
2
represents sulphur.
The invention further preferably relates to sodium salts, potassium salts, calcium salts, ammonium salts, C
1
-C
4
-alkyl-ammonium salts, di-(C
1
-C
4
-alkyl)-ammonium salts, tri-(C
1
-C
4
-alkyl)-ammonium salts, cyclopentyl- or cyclohexyl-ammonium salts and di-(C
1
-C
4
-alkyl)-ammonium salts of compounds of the formula (I) in which Q
1
, R
1
, R
2
, R
3
, R
4
and Z have the meaning given above as preferred.
The invention relates in particular to compounds of the formula (I) in which
Q
1
represents oxygen or sulphur,
R
1
represents hydrogen, fluorine or chlorine,
R
2
represents fluorine, chlorine, bromine, cyano, amino or the grouping —N(A
1
)SO
2
A, in which
A represents a radical selected from the group consisting of methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, ethenyl, propenyl, butenyl, each of which is optionally substituted by fluorine or chlorine, or represents d

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