Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Reexamination Certificate
1999-06-03
2001-10-16
Ford, John M. (Department: 1624)
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
C544S212000, C544S207000, C544S209000, C544S198000
Reexamination Certificate
active
06303541
ABSTRACT:
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted thienyl(amino)sulphonyl(thio)ureas, to processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is already known that certain substituted thienylsulphonylureas have herbicidal propierties (cf. U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,398,939, U.S. Pat. No. 4,523,943). However, the herbicidal activity of these known compounds is not satisfactory in all aspects.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides the novel substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I)
in which
A represents nitrogen or a CH grouping,
E represents a single bond or an NH grouping,
Q represents oxygen or sulphur,
R
1
represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,
R
2
represents hydrogen, halogen or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy, aryloxy or heterocyclyloxy,
R
3
represents hydrogen or optionally substituted alkyl,
R
4
represents cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy,
R
5
represents cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy, and
R
6
represents hydrogen, cyano, halogen or represents in each case optionally substituted alkyl, alkoxy, alkenyl, alkenyloxy, alkinyl or alkinyloxy,
and salts of compounds of the formula (I).
The novel substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I) are obtained when
in the case of E representing a single bond in the general formula (I)
(a) aminoazines of the general formula (II)
in which
A, R
1
, R
2
and R
3
are each as defined above,
are reacted with thienylsulphonyl iso(thio)cyanates of the general formula (III)
in which
Q, R
4
, R
5
and R
6
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(b) substituted aminoazines of the general formula (IV)
in which
A, Q, R
1
, R
2
and R
3
are each as defined above and
z represents halogen, alkoxy or aryloxy,
are reacted with thiophenesulphonainides of the general formula (V)
in which
R
4
, R
5
and R
6
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(c) aminoazines of the general formula (II)
in which
A, R
1
, R
2
and R
3
are each as defined above,
are reacted with substituted thiophenesulphon(thio)aniides of the general formula (VI)
in which
Q, R
4
, R
5
and R
6
are each as defined above and
Z represents halogen, alkoxy or aryloxy,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when—in the case that E represents an NH grouping
(d) arinoazines of the general formula (II)
in which
A, R
1
, R
2
and R
3
are each as defined above
are reacted with chlorosulphonyl iso(thio)cyanate, if appropriate in the presence of a diluent, and the resulting chlorosulphonylureas of the general formula (VII)
in which
A, Q, R
1
, R
2
and R
3
are each as defined above
are reacted with aminothiophenes of the general formula (VIII)
in which
R
4
, R
5
and R
6
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) are optionally converted into salts by customary methods.
The novel substituted thienyl(amino)sulphonyl(thio)ureas of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which
A represents nitrogen or a CH grouping,
E represents a single bond or an NH grouping,
Q represents oxygen or sulphur,
R
1
represents hydrogen, halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,
R
2
represents hydrogen or halogen, represents in each case optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents in each case optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted phenoxy, oxetanyloxy, furyloxy or tetrahydrofuryloxy,
R
3
represents hydrogen or optionally C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl- or C
1
-C
4
-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms,
R
4
represents cyano, halogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyl or C
2
-C
4
-alkinyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkoxy, or represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyloxy or C
2
-C
4
-alkinyloxy,
R
5
represents cyano, halogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyl or C
2
-C
4
-alkinyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkoxy, or represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyloxy or C
2
-C
4
-alkinyloxy, and
R
6
represents hydrogen, represents cyano, halogen, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkyl, represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyl or C
2
-C
4
-alkinyl, represents optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted C
1
-C
4
-alkoxy, or represents in each case optionally cyano- or halogen-substituted C
2
-C
4
-alkenyloxy or C
2
-C
4
-alkinyloxy.
The invention furthermore preferably provides sodium, potassium, magnesium, calcium, ammonium, C
1
-C
4
-alkyl-ammonium, di-(C
1
-C
4
-alkyl)-ammonium, tri-(C
1
-C
4
-alkyl)-ammonium, tetra-(C
1
-C
4
-alkyl)-ammonium, tri-(C
1
-C
4
-alkyl)-sulphonium, C
5
- or C
6
-cycloalkyl-ammonium and di-(C
1
-C
2
-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which A, E, Q, R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are each preferably as defined above.
The invention in particular provides compounds of the formula (I) in which
A represents nitrogen or a CH grouping,
E represents a single bond or an NH grouping,
Q represents oxygen or sulphur,
R
1
represents hydrogen, fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,
R
2
represents fluorine, chlorine, bromine or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino,
R
3
represents hydrogen or optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl, n- or i-butyroyl-, methoxycarbony
Dollinger Markus
Gesing Ernst Rudolf F.
Jansen Johannes Rudolf
Muller Klaus-Helmut
Philipp Ulrich
Bayer Aktiengesellschaft
Ford John M.
Gil Joseph C.
Zurcher Jackie Ann
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