Substituted aryl sulphonyl (thio) ureas as herbicides

Details Substituted aryl sulphonyl (thio) ureas as herbicides Substituted aryl sulphonyl (thio) ureas as herbicides

1998-08-28

2002-09-17

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S213000, C544S197000, C544S198000, C544S206000, C544S207000, C544S208000, C544S209000, C544S211000, C544S212000

Reexamination Certificate

active

06451737

ABSTRACT:

The present invention relates to novel substituted arylsulphonyl(thio)ureas, to processes for their preparation and to their use as herbicides.
It is already known that certain substituted sulphonylureas have herbicidal properties (cf. DE 2715786, EP 1514, EP 23422). However, the herbicidal activity and the crop plant safety of these compounds is not satisfactory in all aspects.
This invention, accordingly, provides the novel substituted arylsulphonyl(thio)ureas of the general formula (I)
in which
A represents nitrogen or a CH grouping,
Q represents oxygen or sulphur,
R
1
represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy,
R
2
represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or heterocyclyloxy,
R
3
represents hydrogen or optionally substituted alkyl,
R
4
represents respectively optionally substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl, and
R
5
represents hydrogen, formyl or respectively optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl or heterocyclyl,
and salts of compounds of the formula (I), except for the prior-art compound N-(4,6-dimethyl-pyrimidin-2-yl)-N′-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea (cf. EP 23422) which is excluded by disclaimer.
The novel substituted arylsulphonyl(thio)ureas of the general formula (I) are obtained when
(a) aminoazines of the general formula (II)
 in which
A, R
1
and R
2
are each as defined above,
are reacted with arylsulphonyl iso(thio)cyanates of the general formula (III)
in which
Q, R
4
and R
5
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
and R
2
are each as defined above,
Z represents halogen, alkoxy or aryloxy and
R
3
is as defined above or represents the grouping —C(Q)—Z
are reacted with arenesulphonamides of the general formula (V)
in which
R
4
and R
5
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
and R
2
are each as defined above,
are reacted with substituted arenesulphonamides of the general formula (VI)
in which
Q, R
4
and R
5
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,
and the compounds of the formula (I) obtained by processes (a), (b) and (c) are, if appropriate, converted into salts by customary methods.
The novel substituted arylsulphonyl(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,
Q represents oxygen or sulphur,
R
1
represents hydrogen, halogen, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or di-alkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents respectively 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 respectively optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy.
R
2
represents hydrogen or halogen, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or di-alkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents respectively 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 respectively optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted 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 respectively optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents respectively optionally halogen-substituted alkenyl, alkinyl, alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkyloxy or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety,
R
5
represents hydrogen, formyl, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, represents respectively optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or represents respectively optionally cyano-, halogen-, C
1
-C
4
-alkyl- or C
1
-C
4
-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl,
except for the prior-art compound N-(4,6-dimethyl-pyrimidin-2-yi)-N′-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea (cf. EP 23422) which is excluded by disclaimer.
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, Q, R
1
, R
2
, R
3
, R
4
and R
5
are each preferably as defined above.
The invention provides in particular compounds of the formula (I) in which
A represents nitrogen or a CH grouping,
Q represents oxygen or sulphur,
R
1
represents hydrogen, fluorine, chlorine. bromine or respectively 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 respectively 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-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl,
R
4
represents respectively optionally cyano- fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl, butinyl, propenyloxy, butenyloxy, propinyloxy or butinyloxy, or represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
R
5
r

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