Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1997-07-18
1999-10-26
Morris, Patricia L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
5482632, 5482634, 5482638, 5482646, A01N 43653, C07D24912
Patent
active
059728442
DESCRIPTION:
BRIEF SUMMARY
The invention relates to sulphonylamino(thio)carbonyl-triazolin(ethi)ones containing at least one thiocarbonyl group [--C(.dbd.S)--], to a plurality of processes for their preparation, and to their use as herbicides.
It is known that certain sulphonylaminocarbonyltriazolinones have herbicidal properties (cf. EP-A 341489, EP-A 422469, EP-A 425948, EP-A 431291). However, sulphonylamino(thio)carbonyl-triazolin(ethi)ones having at least one thiocarbonyl group have hitherto not been disclosed.
This invention, then, provides the novel sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) ##STR2## in which
Q.sup.1 represents oxygen or sulphur,
Q.sup.2 represents oxygen or sulphur,
R.sup.1 represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylamino, cycloalkylalkyl, aryl and arylalkyl,
R.sup.2 represents hydrogen, hydroxyl, mercapto, amino, halogen or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylamino, alkenylamino, alkinylamino, dialkylamino, alkanoylamino, aziridino, pyrrolidino, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino and arylalkylamino, or
R.sup.1 and R.sup.2 together represent optionally branched alkanediyl, and
R.sup.3 represents respectively optionally substituted aryl, arylalkyl or heteroaryl, represent sulphur, and salts of the compounds of the formula (I).
The novel sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) are obtained when
(a) triazolin(ethi)ones of the general formula (II) ##STR3## in which
Q.sup.1, R.sup.1 and R.sup.2 are each as described above, are reacted with sulphonyl iso(thio)cyanates of the general formula (III)
Q.sup.2 and R.sup.3 are each as described above, in the presence of a diluent, or
(b) triazolin(ethi)one derivatives of the general formula (IV) ##STR4## in which
Q.sup.1, Q.sup.2, R.sup.1 and R.sup.2 are each as described above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy, are reacted with sulphonamides of the general formula (V)
R.sup.3 is as described above, the presence of a diluent, or
(c) triazolin(ethi)ones of the general formula (II) ##STR5## in which
Q.sup.1, R.sup.1 and R.sup.2 are each as described above, are reacted with sulphonamide derivatives of the general formula (VI)
Q.sup.2 and R.sup.3 are each as described above and
Z represents halogen, alkoxy, aryloxy or arylalkoxy, the presence of a diluent, or
(d) triazolin(ethi)ones of the general formula (II) ##STR6## in which
Q.sup.1, R.sup.1 and R.sup.2 are each as described above, are reacted with sulphonyl halides of the general formula (VII)
R.sup.1 is as described above and
X represents halogen,
Q.sup.2 is as described above and
M represents an alkali metal or an alkaline earth metal equivalent, in the presence of a diluent, and the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) are, if desired, converted into salts by customary methods.
The novel sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) have strong herbicidal action.
The invention preferably relates to compounds of the formula (I) in which
Q.sup.1 represents oxygen or sulphur,
Q.sup.2 represents oxygen or sulphur,
R.sup.1 represents hydrogen, hydroxyl or amino, or represents C.sub.2 -C.sub.10 -alkylideneamino or represents optionally fluorine-, chlorine-, bromine-, cyano-, C.sub.1 -C.sub.4 -alkoxy-, C.sub.1 -C.sub.4 -alkyl-carbonyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted C.sub.1 -C.sub.6 -alkyl, or represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.su
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Angewandte Chemie, 81.Jahrgang, Heft 13, 1969, Seite 475-506.
Abstract 95:203841j; 28-Heterocycles Vo. 95, 1981, p. 673.
Dollinger Markus
Gesing Ernst Rudolf F
Kluth Joachim
Konig Klaus
Muller Klaus-Helmut
Bayer Aktiengesellschaft
Morris Patricia L.
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