Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1995-04-07
1996-09-03
Morris, Patricia L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504196, 504197, 504225, 504248, 544132, 546210, 548112, 5482632, 5482634, 5482638, 5482646, A01N 4738, A01N 5732, C07D24912, C07D41304
Patent
active
055523692
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new sulphonylaminocarbonyltriazolinones, to a plurality of processes and novel intermediates for their preparation, and to their use as herbicides.
It has already been disclosed that certain sulphonylaminocarbonyltriazolinones, such as, forexample,4,5-dimethyl-2-(2-chlorophenylsulphonyl-aminocarbonyl)-2,4-dihy dro-3H-1,2,4-triazol-3-one, have herbicidal properties (cf. EP-A 341489/LeA 26062; cf. also EP-A 422469/LeA 27154; EP-A 425948/LeA 27155; EP-A 431291/LeA 27156). However, the activity of these compounds is not in all respects satisfactory.
There have now been found the new sulphonylaminocarbonyltriazolinones of the general formula (I) ##STR3## in which Q represents oxygen, sulphur or one of the following groups ##STR4## R.sup.1 represents hydrogen, hydroxyl, amino, alkylideneamino, or represents a radical from the series consisting of alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino, cycloalkylamino, dialkylamino, alkanoylamino and alkoxycarbonylamino, each of which is optionally substituted, represents a radical from the series consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy, alkinyloxy, cycloalkyloxy, aryloxy, aralkyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenylthio, alkinylthio, cycloalkylthio, arylthio, aralkylthio, alkylamino, alkenylamino, arylamino, aralkylamino, dialkylamino, aziridino, pyrrolidino, piperidino or morpholino, each of which is optionally substituted, alkinyl, cycloalkyl, cycloalkylalkyl, alkylsulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, aryl and aralkyl, each of which is optionally substituted, represents alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, aralkoxy, aryloxy or dialkoxy(thio)phosphoryl, each of which is optionally substituted, or the following group Q.sup.1 --R.sup.5, in which substituted,
The new sulphonylaminocarbonyltriazolinones of the formula (I) are obtained when ##STR5## in which R.sup.1 and R.sup.2 have the abovementioned meaning, are reacted with nucleophilic compounds of the general formula (III) presence of an acid acceptor and if appropriate in the presence of a diluent, or when ##STR6## in which R.sup.1 and R.sup.2 have the abovementioned meaning, are reacted with chlorosulphonyl isocyanate, if appropriate in the presence of a diluent, and the resulting chlorosulphonylaminocarbonyltriazolinones of the formula (II)--above--are reacted, without intermediate isolation, with nucleophilic compounds of the general formula (III)--above--if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, (a) or (b) are convened to salts by customary methods.
Other methods which are possible for the preparation of the compounds of the formula (I) according to the invention are given below, Q, R.sup.1, R.sup.2 and R.sup.3 in each case having the abovementioned meaning: formula (IV): ##STR7## (d) Reaction of aminosulphonyl compounds of the formula (VI) with oxycarbonyltriazolinones of the formula (VII) (R: alkyl, aralkyl, aryl): ##STR8## (e) Reaction of sulphonylurethanes of the formula (VIII) with triazolinones of the formula (IV) (R: alkyl, aralkyl, aryl): ##STR9##
The new sulphonylaminocarbonyltriazolinones of the general formula (I) are distinguished by a powerful herbicidal activity.
Surprisingly, the new compounds of the formula (I) display a considerably more powerful herbicidal activity than 4,5-dimethyl-2-(2-chlorophenylsulphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2, 4-triazol-3-one, which is known and which has a similar structure.
The invention preferably relates to compounds of the formula (I) in which ##STR10## R.sup.1 represents hydrogen, hydroxyl, amino, or represents C.sub.2 -C.sub.10 -alkylideneamino, or represents C.sub.1 -C.sub.6 -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl, or represents C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkinyl, each of which is optionally subs
REFERENCES:
patent: 5057144 (1991-10-01), Daum et al.
patent: 5085684 (1992-02-01), Muller et al.
patent: 5238910 (1993-08-01), Muller et al.
Findeisen Kurt
K onig Klaus
Kluth Joachim
Linker Karl-Heinz
M uller Klaus-Helmut
Bayer Aktiengesellschaft
Morris Patricia L.
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