Substituted...

Details Substituted... Substituted...

1998-09-03

2001-03-13

Morris, Patricia L. (Department: 1612)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S263200, C548S263400, C548S263800, C548S264400, C548S264600

Reexamination Certificate

active

06200934

ABSTRACT:

The invention relates to novel substituted arylsulphonylamino(thio)carbonyl-triazolin(ethi)ones, to a plurality of processes for their preparation and to their use as herbicides.
It is already known that certain sulphonylaminocarbonyltriazolinones have herbicidal properties (cf. EP-A 341 489, EP-A 422 469, EP-A 425 948, EP-A 431 291, EP-A 507 171). However, the activity of these compounds is not in all aspects satisfactory.
This invention, accordingly, provides the novel substituted arylsulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I)
in which
Q
1
represents oxygen or sulphur,
Q
2
represents oxygen or sulphur,
R
1
represents hydrogen, amino or represents respectively optionally substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenyl, alkinyl or alkylideneamino,
R
2
represents hydrogen or represents respectively optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, or alkinyl, or together with R
1
represents alkanediyl which is optionally interrupted by oxygen and/or optionally substituted,
R
3
represents hydrogen, cyano, nitro, halogen or represents respectively optionally substituted alkyl, alkylcarbonyl or alkoxycarbonyl, R
4
represents hydrogen, hydroxyl, amino, alkylideneamino or represents a respectively optionally substituted radical from the group alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl, arylalkyl, and
R
5
represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen or represents a respectively optionally substituted radical from the group alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, alkenyl, alkinyl, alkenyloxy, alkinyloxy, alkenylthio, alkinylthio, alkenylamino, alkinylamino, cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, aryl, aryloxy, arylthio, arylamino, arylalkyl,
and salts of compounds of the formula (I).
The novel substituted arylsulphonylamino(thio)carbonyl-triazolinones of the general formula (I) are obtained when
(a) triazolin(ethi)ones of the general formula (II)
in which
Q
1
, R
4
and R
5
are each as defined above are reacted with sulphonyl iso(thio)cyanates of the general formula (III)
in which
Q
2
, R
1
, R
2
and R
3
are each as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(b) triazolin(ethi)one derivatives of the general formula (IV)
in which
Q
1
, Q
2
, R
4
and R
5
are each as defined above and
Z represents halogen, alkoxy, aralkoxy or aryloxy,
are reacted with sulphonamides of the general formula (V)
in which
R
1
, R
2
and R
3
are each as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(c) triazolin(ethi)ones of the general formula (II)
in which
Q
1
, R
4
and R
5
are each as defined above, are reacted with sulphonamide derivatives of the general formula (VI)
in which
Q
2
, R
1
, R
2
and R
3
are each as defined above and
Z represents halogen, alkoxy, aralkoxy or aryloxy,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(d) triazolin(ethi)ones of the general formula (II)
in which
Q
1
, R
4
and R
5
are each as defined above,
are reacted with sulphonyl halides of the general formula (VII)
in which
R
1
, R
2
and R
3
are each as defined above and
X represents halogen,
and metal (thio)cyanates of the general formula (VIII)
MQ
2
CN (VIII)
in which
Q
2
is as defined above and
M represents an alkali metal or alkaline earth metal equivalent,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) are converted into salts by customary methods.
The novel substituted arylsulphonylamino(thio)carbonyl-triazolinones of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which
Q
1
represents oxygen or sulphur,
Q
2
represents oxygen or sulphur,
R
1
represents hydrogen, amino, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, or represents respectively optionally cyano- or halogen-substituted alkenyl, alkinyl or alkylideneamino having in each case 2 to 6 carbon atoms,
R
2
represents hydrogen, 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 cyano- or halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or together with R
1
represents alkanediyl having 2 to 6 carbon atoms, which is optionally interrupted by oxygen and/or optionally substituted by halogen or C
1
-C
4
-alkyl,
R
3
represents hydrogen, cyano, nitro, halogen or represents respectively optionally halogen-substituted alkyl, alkylcarbonyl or alkoxycarbonyl having in each case 1 to 6 carbon atoms in the alkyl groups,
R
4
represents hydrogen, hydroxyl, amino, C
1
-C
6
-alkylideneamino, represents optionally fluorine-, chlorine-, bromine-, cyano-, C
1
-C
4
-alkoxy-, C
1
-C
4
-alkyl-carbonyl- or C
1
-C
4
-alkoxy-carbonyl-substituted C
1
-C
6
-alkyl, represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, represents C
1
-C
6
-alkyloxy or C
3
-C
6
-alkenyloxy, represents respectively optionally fluorine- and/or chlorine-substituted C
1
-C
6
-alkylamino, di-(C
1
-C
4
-alkyl)-amino or C
1
-C
4
-alkanoylamino, represents respectively optionally fluorine-, chlorine-, bromine- and/or C
1
-C
4
-alkyl-substituted C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C
1
-C
4
-alkyl-, trifluoromethyl-, C
1
-C
4
-alkoxy- and/or C
1
-C
4
-alkoxy-carbonyl-substituted phenyl or phenyl-C
1
-C
4
-alkyl, and
R
5
represents hydrogen, hydroxyl, mercapto, amino, cyano, halogen, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, represents respectively optionally cyano- or halogen-substituted alkenyl, alkinyl, alkenyloxy, alkinyloxy, alkenylthio, alkinylthio, alkenylamino or alkinylamino having in each case 2 to 6 carbon atoms, represents respectively optionally cyano-, halogen- or C
1
-C
4
-alkyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino or cycloalkyl-C
1
-C
4
-alkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or represents optionally cyano-, halogen-, C
1
-C
4
-alkyl-, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy- or C
1
-C
4
-halogenoalkoxy-substituted phenyl, phenoxy, phenylthio, phenylamino or phenyl-C
1
-C
4
-alkyl.
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 Q
1
, Q
2
, R
1
, R
2
, R
3
, R
4
and R
5
are each preferably as defined above.
The invention in particular provides compounds of the formula (I) in which
Q
1
represents oxygen or sulphur,
Q
2
represents oxygen or sulphur,
R
1
represents hydrogen, represents respectively optionally cyano-, fluorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methyl

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