Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-01-09
1999-12-14
Morris, Patricia L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
5482634, C07D24912
Patent
active
060017767
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/02933 filed Jul. 4, 1996.
The invention relates to novel sulphonylamino(thio)carbonyltriazolin(thi)ones having heterocyclyl(alk)oxy substituents, to a number of processes and to novel intermediates for their preparation, and to their use as herbicides.
It is already known that certain sulphonylaminocarbonyltriazolinones possess herbicidal properties (cf. EP-341 489, EP-A 422 469, EP-A 425 948, EP-A 431 291, EP-A 507 171). The action of these compounds, however, is not in every respect satisfactory.
The novel sulphonylamino(thio)carbonyltriazolin(thi)ones having heterocyclyl(alk)oxy substituents have now been found of the general formula (I) ##STR2## in which Q.sup.1 represents oxygen or sulphur, represents an in each case optionally substituted radical from the series consisting of alkyl, alkenyl, alkinyl, alkoxy, alkenytoxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, heterocyclylalkyl, and series consisting of alkyl, aralkyl, aryl and heteroaryl, and salts of compounds of the formula (I).
The novel sulphonylamino(thio)carbonyltriazolin(thi)ones having heterocyclyl(alk)oxy substituents, of the general formula (I), are obtained if ##STR3## in which Q.sup.1, R.sup.1 and R.sup.2 have the meanings given above are reacted with sulphonyl iso(thio)cyanates of the general formula (III) presence of a reaction auxiliary and optionally in the presence of a diluent, or if ##STR4## in which Q.sup.1, Q.sup.2, R.sup.1 and R.sup.2 have the meanings given above and sulphonamides of the general formula (V) acceptor and optionally in the presence of a diluent, ##STR5## in which Q.sup.1, R.sup.1 and R.sup.2 have the meanings given above are reacted with sulphonamide derivatives of the general formula (VI) presence of an acid acceptor and optionally in the presence of a diluent, ##STR6## in which Q.sup.1, R.sup.1 and R.sup.2 have the meanings given above are reacted with sulphonyl halides of the general formula (VII) (VIII) in the presence of a reaction auxiliary and optionally in the presence of a diluent, (b), (c) or (d) are converted into salts by customary methods.
The novel sulphonylamino(thio)carbonyltriazolin(thi)ones having heterocyclyl(alk)oxy substituents, of the general formula (I), are distinguished by a strong herbicidal activity.
The invention relates preferably to compounds of the formula (I) in which -alkylideneamino, or represents optionally fluoro-, chloro-, bromo-, cyano-, C.sub.1 -C.sub.4 -alkoxy-, C.sub.1 -C.sub.4 -alkylcarbonyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted C.sub.1 -C.sub.6 -alkyl, or represents in each case optionally fluoro-, chloro- and/or bromo-substituted C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkinyl, or represents C.sub.1 -C.sub.6 -alkyloxy or C.sub.3 -C.sub.6 -alkenyloxy, or represents in each case optionally fluoro- and/or chloro-substituted C.sub.1 -C.sub.6 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino or C.sub.1 -C.sub.4 -alkanoylamino, or represents in each case optionally fluoro-, chloro-, bromo- and/or C.sub.1 -C.sub.4 -alkyl-substituted C.sub.3 -C.sub.6 -cycloalkyl or C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl, or represents in each case optionally fluoro-, chloro-, bromo-, cyano-, nitro-, C.sub.1 -C.sub.4 -alkyl-, trifluoromethyl-, C.sub.1 -C.sub.4 -alkoxy- and/or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, -C.sub.4 -alkyl-substituted oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, pyridyl, pyrimidyl, oxetanyl-C.sub.1 -C.sub.4 -alkyl, thietanyl-C.sub.1 -C.sub.4 -alkyl, furyl-C.sub.1 -C.sub.4 -alkyl, tetrahydrofuryl-C.sub.1 -C.sub.4 -alkyl, thienyl-C.sub.1 -C.sub.4 -alkyl, tetrahydrothienyl-C.sub.1 -C.sub.4 -alkyl, pyridyl-C.sub.1 -C.sub.4 -alkyl or pyrimidyl-C.sub.1 -C.sub.4 -alkyl, and ##STR7## in which R.sup.4 and R.sup.5 are identical or different and represent hydrogen, fluoro, chloro, bromo, iodo, nitro or C.sub.1 -C.sub.6 -alkyl (which is optionally substituted by fluoro, chlo
REFERENCES:
patent: 5057144 (1991-10-01), Daum et al.
patent: 5534486 (1996-07-01), Muller et al.
Cram and Hammond, "Organic Chemistry", McGraw-Hill Book Co., NY (1964) 2nd Ed, pp. 565-567.
Chemische Berichte, vol. 110, No. 5, 1977, pp. 1716-1729 (in German with English Abstract).
Dollinger Markus
Drewes Mark Wilhelm
Findeisen Kurt
Gesing Ernst Rudolf
Jansen Johannes Rudolf
Bayer Aktiengesellschaft
Morris Patricia L.
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