5,6-dihydro-(1,4,2)-Dioxazin-substituted (hetero)...

Details 5,6-dihydro-(1,4,2)-Dioxazin-substituted (hetero)... 5,6-dihydro-(1,4,2)-Dioxazin-substituted (hetero)...

1999-05-13

2001-03-13

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S065000

Reexamination Certificate

active

06200931

ABSTRACT:

This aplication is a 371 of PCT/EP97/04233, filed Aug. 4, 1997.
TECHNICAL FIELD OF THE INVENTION
The invention relates to novel substituted sulphonylamino(thio)carbonyl compounds, to a plurality of processes for their preparation and to their use as herbicides.
BACKGROUND OF THE INVENTION
It is known that certain substituted sulphonylamino(thio)carbonyl compounds have herbicidal properties (cf. EP 341 489, EP 422 469, EP 425 948, EP 431 291, EP 507 171, EP 534 266, EP 569 810, DE 40 29 753). However, the activity of these compounds is not satisfactory in every respect.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel substituted sulphonylamino(thio)carbonyl compounds of the general formula (I)
in which
A represents a single bond, represents oxygen, imino (NH), alkanediyl (alkylene) or alkylimino (N-alkyl),
J represents a (hetero)aryl grouping selected from the series phenyl, pyridyl, pyrazolyl, thienyl which is substituted by a 5,6-dihydro-[1,4,2]-dioxazin-3-yl group (which may for its part be substituted by halogen, alkyl or halogenoalkyl) and optionally by one or two further radicals selected from the series cyano, halogeno, alkyl, halogenoalkyl, phenyl, pyridyl,
Q represents oxygen or sulphur and,
R represents optionally substituted heterocyclyl having 5 ring members of which at least one is oxygen, sulphur or nitrogen and one to three more may be nitrogen,
and salts of compounds of the formula (I).
The novel substituted sulphonylamino(thio)carbonyl compounds of the general formula (I) are obtained when
(a) aminosulphonyl compounds of the general formula (II)
 in which
A and J are each as defined above
are reacted with (thio)carboxylic acid derivatives of the general formula (III)
 in which
Q and R are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(b) sulphonyl iso(thio)cyanates of the general formula (IV)
 in which
A, J and Q are each as defined above
are reacted with heterocycles of the general formula (V)
H—R (V)  (V)
 in which
R is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or when
(c) chlorosulphonyl compounds of the general formula (VI)
 in which
A and J are each as defined above
are reacted with heterocycles of the general formula (V)
H—R  (V)
 in which
R is as defined above
and metal (thio)cyanates of the general formula (VII)
MQCN  (VII)
 in which
Q 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,
or when
(d) chlorosulphonyl compounds of the general formula (VI)
 in which
A and J are each as defined above
are reacted with (thio)carboxamides of the general formula (VIII)
 in which
Q and R 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
(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)
 in which
A, J and Q are each as defined above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy
are reacted with heterocycles of the general formula (V)
H—R  (V)
 in which
R is as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
or when
(f) heterocycles of the general formula (V)
H—R  (V)
 in which
R is as defined above
are reacted with chlorosulphonyl iso(thio)cyanate, if appropriate in the presence of a diluent, and the adducts, formed in the process, of the general formula (X)
 in which
Q and R are each as defined above
are reacted in situ with (hetero)aryl compounds of the general formula (XI)
 in which
A and J are each as defined above,
if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent,
and the compounds of the formula (I) obtained by the processes (a), (b), (c), (d), (e) or (f) are, if appropriate, converted into salts by customary methods.
The novel substituted sulphonylamino(thio)carbonyl compounds of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which
A represents a single bond, represents oxygen, imino (NH), C
1
-C
4
-alkanediyl or C
1
-C
4
-alkylimino,
J represents a (hetero)aryl grouping selected from the series phenyl, pyridyl, pyrazolyl, thienyl which is substituted by a 5,6-dihydro-[1,4,2]-dioxazin-3-yl group (which may for its part be substituted by halogen, C
1
-C
4
-alkyl or C
1
-C
4
-halogenoalkyl) and optionally by one or two further radicals selected from the series cyano, halogen, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, phenyl, pyridyl,
Q represents oxygen or sulphur and
R represents heterocyclyl of the formulae below, each of which is optionally substituted,
 in which
Q
1
, Q
2
and Q
3
each represent oxygen or sulphur and
R
1
represents hydrogen, hydroxyl, amino, cyano, represents C
2
-C
10
-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 C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, represents C
1
-C
6
-alkoxy, C
1
-C
6
-alkylamino or C
1
-C
6
-alkyl-carbonylamino, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, C
1
-C
4
-alkoxy or C
1
-C
4
-alkoxy-carbonyl, represents C
3
-C
6
-alkenyloxy, represents di-(C
1
-C
4
-alkyl)-amino, represents C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkylamino or C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano and/or C
1
-C
4
-alkyl, or represents phenyl or phenyl-C
1
-C
4
-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C
1
-C
4
-alkyl, trifluoromethyl and/or C
1
-C
4
-alkoxy,
R
2
represents hydrogen, hydroxyl, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, 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 C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, represents C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
1
-C
6
-alkylamino or C
1
-C
6
-alkyl-carbonylamino, each of which is optionally substituted by fluorine, chlorine, cyano, C
1
-C
4
-alkoxy or C
1
-C
4
-alkoxy-carbonyl, represents C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkinyloxy, C
3
-C
6
-alkenylthio, C
3
-C
6
-alkinylthio, C
3
-C
6
-alkenylamino or C
3
-C
6
-alkinylamino, represents di-(C
1
-C
4
-alkyl)-amino, represents aziridino, pyrrolidino, piperidino or morpholino, each of which is optionally substituted by methyl and/or ethyl, represents C
3
-C
6
-cycloalkyl, C
5
-C
6
-cycloalkenyl, C
3
-C
6
-cycloalkyloxy, C
3
-C
6
-cycloalkylthio, C
3
-C
6
-cycloalkylamino, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkoxy, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkylthio, or C
1
-C
4
-cycloalkyl-C
1
-C
4
-alkylamino, each of which is optionally substituted by fluorine, chlorine, bromine, cyano and/or C
1
-C
4
-alkyl, or represents phenyl, phenyl-C
1
-C
4
--alkyl, phenoxy, phenyl-C
1
-C
4
-alkoxy, phenylthio, phenyl-C
1
-C
4
-alkylthio, phenylamino or phenyl-C
1
-C
4
-alkylamino, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C
1
-C
4
-alkyl, trifluoromethyl, C
1
-C
4
-alkoxy and/or C
1
-C
4
-alkoxy-carbonyl, or
R
1
and R
2
together represent optionally branched alkanediyl having 3 to 11 carbon atoms, furthermore,
R
3
, R
4
and R
5
are identical or different and each represents hydrocen, cyano, fluorine, chlorine, bromine, or

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