Substituted sulphonylaminocarbonyltriazolinones and their use as

Details Substituted sulphonylaminocarbonyltriazolinones and their use as Substituted sulphonylaminocarbonyltriazolinones and their use as

1996-09-30

1999-01-19

Morris, Patricia L.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

5482632, 5482634, 5482638, 5482644, A01N 4738, C07D24912

Patent

active

058613587

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel substituted sulphonylaminocarbonyltriazolinones, to several processes for their preparation and to their use as herbicides.
It is already known tat certain sulphonylaminocarbonyltriazolinones, such as 4,5-dinethyl-2-(2-chloro-phenylphonyl-aminocarbonyl)-2,4-dihydro-3H-1,2 ,4-triazol-3-one, exhibit herbicidal properties (cf. EP-A 341 489; cf also EP-A 422 469; EP-A 425 948; EP-A 431 291). However, the effect of these compounds is not satisfactory in all respects.
The novel sulphonylamiocarbonyltriazolinones of the general formula (I), ##STR1## in which Q represents oxygen, sulphur or the grouping --N(R.sup.4)--, represents a radical, which is in each case optionally substituted, from the group alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino, cycloalkylamino, dialkylamino and alkanoylamino, represents a radical, which is in each case optionally substituted, from the group 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 and morpholino, least twice, where one of the substituents is different from alkyl, represents optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, aralkoxy, aryloxy or dialkoxy(thio)phosphoryl, or represents the following grouping Q.sup.1 --R.sup.5, in which optionally substituted,
The novel sulphonylaminocarbonyltriazolinones of the formula (I) are obtained if ##STR2## in which R.sup.1 and R.sup.2 have the abovementioned meaning, in the presence of a diluent, ##STR3## in which R.sup.1 and R.sup.2 have the abovementioned meaning, presence of a diluent, and the resulting chlorosulphonylarinocarbonyltriazolinones of the formula (II)--above--are reacted, without intermediate isolation, with nucleophilic compounds of the general formula (III)--above--, where appropriate in the presence of an acid acceptor and where appropriate in the presence of a diluent, by processes (a) or (b) are converted into salts using customary methods.
Further possible methods for preparing the novel compounds of the formula (I) are listed below, with Q, R.sup.1, R.sup.2 and R.sup.3 in each case having the abovementioned meaning: formula (IV): ##STR4## (d) reaction of aminosulphonyl compounds of the formula (VI) with oxycarbonyltriazolinones of the formula (VII) (R: alkyl, aralkyl or aryl): ##STR5## (e) reaction of sulphonylurethanes of the formula (VIII) with triazolinones of the formula (IV) (R: alkyl, aralkyl or aryl): ##STR6## The novel sulphonylaminocarbonyltriazolinones of the general formula (I) are notable for their powerful herbicidal activity.
Surprisingly, the novel compounds of the formula (I) exhibit a substantially more powerful herbicidal effect than structurally similar, known 4,5-dimethyl-2-(2-chlorophenylsulphonyl-aminocarbonyl)-2, 4dihydro-3H-1,2,4-triazol-3-one.
The invention preferably relates to compounds of the formula (I), in which -C.sub.10 -alkylidenamino, 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, represents C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkinyl which are in each case optionally substituted by fluorine, chlorine and/or bromine, represents C.sub.3 -C.sub.6 -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C.sub.1 -C.sub.4 -alkyl, represents phenyl-C.sub.1 -C.sub.3 -ally which is optionally substituted by fluorine, chlorine, bromine, 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 -alkoxycarbonyl, represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C.sub.1- C.sub.4 -alkyl, trifluoromethyl, C.sub.l -C.sub.4 -alkoxy, fluorine- and/or c

REFERENCES:
patent: 5057144 (1991-10-01), Daum et al.
patent: 5552369 (1996-09-01), Findeisen et al.

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