CA2211411C - Sulphonyl amino(thio)carbonyl-1,2,4-triazolin(thi)one derivatives, the production thereof and the use thereof as herbicides - Google Patents

Abstract

The invention relates to sulphonylamino(thio)carbonyl-triazolin(ethi)ones of the general formula (I) (see formula I) in which Q1 represents oxygen or sulphur, Q2 represents oxygen or sulphur, R1 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, R2 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 R1 and R2 together represent optionally branched alkanediyl, and R3 represents respectively optionally substituted aryl, arylalkyl or heteroaryl, - with the proviso that either Q1 or Q2'- represents sulphur or both represent sulphur -, and to salts of the compounds of the formula (I), furthermore to a plurality of processes for preparing the novel compounds of the formula (I) and the salts thereof and to the use of these compounds as herbicides.

Description

E. r~ s .. r Le A 30 882-Foreign countries / Bi/Kr/S-P

.n ~,. eon [~ per~ ~~ t T-~' TRA,~a~LbTtQM
Sulphonylamino(thio)ca~onyl-triazoli~ethi)ones The invention relates to sulphonylamino(thio)carbonyl-triazolin(ethi)ones containing at least one thiocarbonyl group [-C(=S)-J, 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) Q, R
l ~ ~ , R~
SOz,NH N
N
Rz in which Q' represents oxygen or sulphur, QZ represents oxygen or sulphur, R' 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, yt .. -M
. ' Le A 30 882-Foreign countries / BilKr/S-P

R'- 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' and Rz together represent optionally branched alkanediyl, and R3 represents respectively optionally substituted aryl, arylalkyl or heteroaryl, - with the proviso that either Q' or Qz represents sulphur or both 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) Q, H~N~N~R' N
Rz in which Q', R' and RZ are each as described above, are reacted with sulphonyl iso(thio)cyanates of the general formula (III) Le A 30 882-Foreign countries R3-SOZ N=C=Q'- (III) in which Q'- and R3 are each as described above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or (b) triazolin(ethi)one derivatives of the general formula (IV) Qz Q' R' ~N~N
(IV) N
Rz in which Q', QZ, R' and RZ are each as described above and Z represents halogen, alkoxy, aryloxy or arylalkoxy, are reacted with sulphonamides of the general formula (V) R3-SOZ-NHS (V) in which R3 is as described above, ~ Le A 30 882-Foreign countries if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or (c) triazolin(ethi)ones of the general formula (II) Q, H~N~N~R' v (i1) N

in which Q', R' and RZ are each as described above, are reacted with sulphonamide derivatives of the general formula (VI) R3-SOZ NH-CQZ-Z (VI) in which QZ and R3 are each as described 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 (d) triazolin(ethi)ones of the general formula (II) Le A 30 882-Foreign countries Q, H,N~N,R' N =C

in which Q', Rl and RZ are each as described above, are reacted with sulphonyl halides of the general formula (VII) R3-SOZ-X (VII) in which R3 is as described above and X represents halogen, and metal (thio)cyanates of the general formula (VIII) MQZCN (VIII) in which QZ is as described above and M represents an alkali metal or an alkaline earth metal equivalent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, s Le A 30 882-Foreign countries' 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 mover su~p~onylainirio(thio)carbonyl=triazolin(ethi)ories of-the general formula (I) have strong herbicidal action.
The invention preferably relates to compounds of the formula (I) in which Q' represents oxygen or sulphur, Q' represents oxygen or sulphur, R' represents hydrogen, hydroxyl or amino, or represents Cz-C,o alkylideneamino or represents optionally fluorine-, chlorine-, bromine-, cyano-, C,-C4 alkoxy-, C,-C4 alkyl-carbonyl- or C,-C4 alkoxy-carbonyl-substituted C,-C6 alkyl, or represents respectively optionally fluorine-, chlorine- and/or bromine-substituted CZ C6 alkenyl or CZ C6-alkinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, C,-C4 alkoxy- or C,-C4-alkoxy-carbonyl-substituted C,-C6-alkoxy, C,-C6-alkylamino or C1-C6-alkanoylamino, or represents C3-C6-alkenyloxy, or represents di-(C,-C4-alkyl)-amino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano- and/or C1-C4 alkyl-substituted C3-C6 cycloalkyl, C3-C6-cycloalkylamino or C3-C6-cycloalkyl-C,-C4 alkyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, CI-C4-alkyl-, trifluoromethyl- and/or CI-C4 alkoxy-substituted phenyl or phenyl-C,-C4-alkyl, RZ represents hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine, bromine or iodine, or represents optionally fluorine-, chlorine-, bromine-, cyano-, C,-C4-alkoxy-, C,-C4-alkyl-carbonyl- or C,-C4-alkoxy-carbonyl-substituted C,-C6-alkyl, or represents respectively optionally fluorine-, chlorine- and/or bromine-substituted CZ-C6-alkenyl or CZ C6-alkinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted Le A 30 882-Foreign' countries CI-C6-alkoxy, C,-C6-alkylthio, C,-C6-alkylamino or C,-C6-alkanoylamino, or represents C3-C6-alkenyloxy, C3-C6 alkinyloxy, C;-C6-alkenylthio, C3-C6-alkinylthio, C3-C6-alkenylamino or C3-C6-alkinylamino, or represents di-(C,-C4-alkyl)-amino, or represents respectively optionally methyl- and/or ethyl-substituted aziridino, pyrrolidino, piperidino or morpholino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano- and/or C,-C4 alkyl-substituted C3-C6-cycloalkyl, CS-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C3-C6 cycloalkylthio, C3-C6-cycloalkylamino, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6 cycloalkyl-C,-C4-alkoxy, C3-C6-cycloalkyl-CI-C4-alkylthio or C3-C6-cycloalkyl-C,-C4-alkylamino, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, vitro-, C~-C4-alkyl-, trifluoromethyl- and/or C,-C4-alkoxy-substituted phenyl, phenyl-C,-C4-alkyl, phenoxy, phenyl-C,-C4-alkoxy, phenylthio, phenyl-C,-C4-alkylthio, phenylamino or phenyl-C,-C4-alkylamino, or R' and R' together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and Rs R3 represents the grouping \ /
Ra in which R4 and RS are identical or different and each represent hydrogen, fluorine, chlorine, bromine, iodine, vitro, C,-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C,-C4-alkoxycarbonyl, CI-C4-alkylamino-carbonyl, di-(C,-C4-alkyl)-amino-carbonyl, hydroxyl, C,-C4-alkoxy, formyloxy, C,-C4-alkyl-carbonyloxy, C,-C4 alkoxy-carbonyloxy, C,-C4 alkylamino-carbonyloxy, C,-C4 Le A 30 882-Foreign countries _g_ alkylthio, C,-C4 alkylsulphinyl, C,-C4 alkylsulphonyl, di-(C,-C4-alkyl)-aminosulphonyl, C3-C6-cycloalkyl or phenyl), or represent C~-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, CI-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent CZ C6-alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C,-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent C,-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C,-C4 alkoxy-carbonyl, C,-C4-alkoxy, C,-C4-alkylthio, CI-C4-alkylsulphinyl or C,-C4-alkylsulphonyl), or represent C,-C4 alkylthio (which is optionally .substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4 alkoxy-carbonyl, C~-C4-alkylthio, C,-C4-alkylsulphinyl or C,-C4 alkylsulphonyl), or represent CZ-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4 alkoxy-carbonyl), or represent CZ-C6 alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, vitro, C,-C3-alkylthio or C~-C4 alkoxy-carbonyl), C3-C6-alkinyloxy, C3-C6-alkinylthio, or represent the radical -S(O)P R6 in which p represents the numbers 1 or 2 and R6 represents C1-C4 alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C,-C4-alkoxy-carbonyl), C3-C6-alkenyl, C3-C6-alkinyl, Ci-C4-alkoxy, C,-C4-alkoxy-C,-C4 alkylamino, C1-C4 alkylamino, di-(CI-C4-alkyl)-a.>nino or phenyl, or represent the radical -NHOR' in which R' represents C,-C,2-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C,-C4-alkoxy, C~-C4-alkylthio, C,-C4-alkylsulphinyl, C1-C4 alkylsulphonyl, C~-C4-alkyl-carbonyl, C~-C4 alkoxy-carbonyl, C,-C4 alkylamino-carbonyl . or di-(C I-C4-alkyl)-amino-carbonyl), or represents C3-C6-alkenyl (which is optionally substituted ' CA 02211411 1997-07-24 Le A 30 882-Foreign countries by fluorine, chlorine or bromine), C;-C6 alkinyl, C3-C6 cycloalkyl, C3-C6-cycloalkyl-C,-C,-alkyl or phenyl-C,-Cz-alkyl (which is optionally substituted by fluorine, chlorine, vitro, cyano, C,-C4-alkyl, C,-C4-alkoxy or C,-C4-alkoxy-carbonyl), or represents benzhydryl or represents phenyl (which is optionally substituted by fluorine, chlorine, vitro, cyano, C,-C4-alkyl, trifluoromethyl, C,-C4-alkoxy, C,-C,-fluoroalkoxy, C,-C4 alkylthio, trifluoromethylthio or C,-C4-alkoxy-carbonyl), R4 and RS further represent phenyl or phenoxy, or represent C,-C4 alkyl-carbonylamino, C,-C4 alkoxy-carbonylamino,C,-C4 alkylamino-carbonyl-amino or di-(C,-C4 alkyl)-amino-carbonylamino, or represent the radical -CO-Rg in which Rg represents hydrogen, C,-C6-alkyl, C3-C6-cycloalkyl, C,-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C,-C4-alkylthio, C,-C4-alkylamino, C,-C4-alkoxyamino, C,-C4 alkoxy-C,-C4-alkyl-amino or di-(C,-C4 alkyl)-amino (each of which is optionally substituted by fluorine and/or chlorine), R4 and/or RS further represent trimethylsilyl, thiazolinyl, C,-C4 alkyl sulphonyloxy or di-(C,-C4-alkyl)-aminosulphonylamino, or represent the radical -CH=N-R9 in which R9 represents optionally fluorine-, chlorine-, cyano-, carboxyl-, C,-C4-alkoxy-, C,-C4-alkylthio-, C,-C4 alkylsulphinyl- or C,-C4-alkylsulphonyl-substituted C,-C6-alkyl, or represents optionally fluorine- or chlorine-substituted benzyl, or represents optionally fluorine- or chlorine-substituted C3-C6-alkenyl or C3-C6-alkinyl, or represents optionally fluorine-, chlorine-, bromine-, C,-C4 alkyl-, C,-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy- or a Le A 30 882-Foreign countries trifluoromethylthio-substituted phenyl, or represents optionally fluorine- and/or chlorine-substituted C,-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or benzyloxy, or represents amino, C,-C4-alkylamino, di-(C,-C4-alkyl)-amino, phenylamino, C,-C4-alkyl-carbonyl-amino, CI-C4-alkoxy-carbonylamino or C,-C4-alkyl-sulphonylamino, or represents optionally fluorine-, chlorine-, bromine- or methyl-substituted phenylsulphonylamino, furthermore, R, o D, 2 R3 represents the radical -CH
\ /
R"
in which R'° represents hydrogen or C,-C4-alkyl, R" and R'2 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, CI-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C,-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C,-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C,-C4-alkylsulphonyl or di-(CI-C4 alkyl)-aminosulphonyl;
furthermore, R3 represents the radical R,3 , Le A 30 882-Foreign countries in which R'3 and R'4 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, vitro, cyatlo, C~-C4-alkyl (which is optionally substituted by fluorine and/or chlorine) or C,-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine);
furthermore, R~s R3 represents the radical w N R~s in which R'S and R'6 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, vitro, cyano, C,-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C,-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C,-C4-alkylthio, C,-C4-alkylsulphinyl or C,-C4-alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl or mono-(C,-C4-alkyl)-aminosulphonyl, or represent di-(C,-C4 alkyl)-aminosulphonyl or C,-C4-alkoxy-carbonyl or dimethyl-aminocarbonyl;
furthermore, r a Le A 30 882-Foreign countries' R3 represents the radical R'~ ~ ~ R'8 N
in which R" and R'8 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, CI-C4-alkyl (which is optionally substituted by fluorine and/or bromine), C,-C4 alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C1-C4-alkylthio, C,-C4-alkylsulphinyl or C,-C4-alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), or represent di-(C,-C4 alkyl)-aminosulphonyl;
furthermore, R'9 R3 represents the radical ~ ~ Rzo A
in which R'9 and RZ° are identical or different and each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C,-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C,-C4 alkoxy (which is optionally substituted by fluorine and/or chlorine), C,-C4-alkylthio, C,-C4-alkylsulphinyl or C,-C4 alkylsulphonyl (each of which is optionally substituted by fluorine and/or chlorine), di-(C,-C4-alkyl)-amino-sulphonyl, C,-C4-alkoxy-carbonyl or dimethylaminocarbonyl, and r Le A 30 882-Foreign countries A represents oxygen, sulphur or the grouping N-Z' in which Z' represents hydrogen, C1-C4 alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-C6-cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C,-C4-alkyl-carbonyl, C1-C4 alkoxy-carbonyl or di-(C1-C4 alkyl)-amino-carbonyl;
furthermore, Rz~
R3 represents the radical ~ ~ R22 Y' in which RZ' and RZZ are identical or different and each represent hydrogen, C,-C4-alkyl, halogen, C,-C4-alkoxy-carbonyl, C,-C4-alkoxy or C~-C4 halogenoalkoxy, Y' represents sulphur or the grouping N-R23 in which R23 represents hydrogen or C1-C4-alkyl;
furthermore, Rzs R3 represents the radical NI ' ~R25 ~N
Rza ,;

Le A 30 882-Foreign countries in which R'4 represents hydrogen, C,-C4 alkyl, benzyl, pyridyl, quinolinyl or phenyl, R'-5 represents hydrogen, halogen, cyano, nitro, CI-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), CI-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C,-C4 alkoxy-carbonyl, and R26 represents hydrogen, halogen or C,-C4 alkyl, and furthermore, R3 represents one of the groupings listed below ~ ~ ~N' N~
O
~SOZ C4H9 . ~g OCH2CF3 .
O
- with the proviso that either Q' or QZ represents sulphur or that both represent sulphur.
The invention further preferably relates to the sodium, potassium, magnesium, calcium, ammonium, C,-C4-alkyl-ammonium, di-(C,-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-ammonium, tetra-(CI-C4-alkyl)-ammonium, tri-(C1-C4 alkyl)-sulphonium, CS- or cycloalkyl-ammonium and di-(C,-Cz alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which Q', Q2; R', Rz and R3 are preferably as defined above.
The invention in particular relates to compounds of the formula (I) in which Q1 represents oxygen or sulphur, Le A 30 882-Foreign countries QZ represents oxygen or sulphur, R' represents hydrogen, hydroxyl or amino, or represents C3-C$-alkylideneamino or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy or butenyloxy, or represents dimethylamino or diethylamino, or represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexyl amino, cyclopropylmethyl; cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl or benzyl, RZ represents hydrogen, hydroxyl, mercapto, amino, fluorine, chlorine' or bromine, or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethylamino or dipropylamino, or represents respectively optionally fluorine-, chlorine-, methyl- and/or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, ,a .6 Le A 30 882-Foreign countries cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents respectively optionally fluorine-, chlorine-, methyl-, trifluoromethyl- and/or methoxy-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino, or R' and RZ together represent optionally branched alkanediyl having 3 to 11 carbon atoms, and R3 represents the radical \ /

in which R4 represents fluorine, chlorine or bromine, or represents respectively optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, or represents respectively optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-prcpyls;:'.phcnyl, dimethylGrr:inosulphor_yl, diethylaminosulphonya, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl or phenoxy, or represents respectively optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and a , t Le A 30 882-Foreign countries RS represents hydrogen, methyl, ethyl, fluorine, chlorine or bromine;
furthermore, R"
R3 represents the radical - R~z -cH
Rio in which Rl° represents hydrogen, R" represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and R'z represents hydrogen;
furthermore, R3 represents the radical Ro-c I s in which R represents methyl, ethyl, n- or i-propyl, Le A 30 882-Foreign countries' or Rzs Rzs R3 represents the radical N
Rza in which R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, S R25 represents hydrogen, fluorine, chlorine or bromine, R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl, - with the proviso that either Q' or QZ represents sulphur or that both represent sulphur.
The radical definitions listed above, whether general or in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case for the preparation.
These radical definitions can be combined with one another as desired, thus including combinations between the preferred ranges indicated.
In the definitions of the radicals, hydrocarbon radicals such as alkyl, alkenyl or alkinyl, are, even in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino, even if this is not explicitly stated, straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Le A 30 882-Foreign countries Examples of the meaning of the radicals R', R'- and R3 in the compounds of the formula (I) according to the invention are listed in the groups below.
Group 1 S O
R
SOz,NH N N~R (IA) N

R1 has, for example, the meanings listed below:
amino, n- or i-propylideneamino, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, dichloropropyl, dibromopropyl, methoxypropyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino, n- or i-propylamino, propenyloxy, dimethylamino, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methyl cyclopropyl or cyclopropylmethyl.
R'- has, for example, the meanings listed below:
hydrogen, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, fluoromethylthio, chloromethylthio, fluoroethylthio, chloroethylthio, difluoroethylthio, trifluoroethylthio, trifluoropropylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio~, propenylamino, butenylamino, propinylamino, butinylamino, dimethylamino, diethylamino, N-methyl-ethylamino, N-methyl-propylamino, N-ethyl-propylamino, cyclopropyl, cyclopropyloxy, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropylmethylthio, phenyl, phenoxy, phenylthio, phenylamino, phenylmethyl, phenylmethoxy, phenylmethylthio or phenylmethylamino.

Le A 30 882-Foreign countries Additionally, R' and R'- together have, for example, the following meanings:
propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl and undecane-l,ll-diyl.
R3 has, for example, the meanings listed below:
2-fluoro-phenyl, 2-chloro-phenyl, 2-bromo-phenyl, 2,6-difluoro-phenyl, 2,6-dichloro-phenyl, 2-methyl-phenyl, 2-chloro-6-methyl-phenyl, 2-trifluoromethyl-phenyl, 2-(2-fluoro-ethyl)-phenyl, 2-(2-chloro-ethyl)-phenyl, 2-(3-fluoro-propyl)-phenyl, 2-(3-chloro-propyl)-phenyl, 2-(3,3,3-trifluoro-propyl)-phenyl, 2-(3,3,3-trifluoro-1-propenyl)-phenyl, 2-methoxy-phenyl, 2-ethoxy-phenyl, 2-difluoromethoxy-phenyl, 2-trifluoromethoxy-phenyl, 2-(2-fluoro-ethoxy)-phenyl, 2-(2-chloro-ethoxy)-phenyl, 2-(2-methoxy-ethoxy)-phenyl, 2-methylthio-phenyl, 2-ethylthio-phenyl, 2-methylsulphinyl-phenyl, 2-ethylsulphinyl-phenyl, 2-methylsulphonyl-phenyl, 2-ethylsulphonyl-phenyl, 2-dimethylaminosulphonyl-phenyl, 2-phenyl-phenyl, 2-methoxycarbonyl-phenyl, 2-ethoxycarbonyl-phenyl, 2-chloro-phenylmethyl, 2,6-dichloro-phenylmethyl, 2-difluoromethoxy-phenylmethyl, 2-trifluoromethoxy-phenylmethyl, 2-methoxycarbonyl-phenylmethyl, 2-ethoxycarbonyl-phenylmethyl, 2-methoxycarbonyl-3-thienyl, 2-ethoxycarbonyl-3-thienyl, 4-methoxycarbonyl-1-methyl-5-pyrazolyl, 4-ethoxycarbonyl-1-methyl-5-pyrazolyl, 3-chloro-4-methoxycarbonyl-methyl-5-pyrazolyl, 3-chloro-4-ethoxycarbonyl-1-methyl-5-pyrazolyl, 3-methoxycarbonyl-2-pyridyl, 3-ethoxycarbonyl-2-pyridyl, 3-dimethylaminocarbonyl-2-pyridyl, 3-methylsulphonyl-2-pyridyl or 3-ethylsulphonyl-2-pyridyl.
Group 2 O S
R
R~
SOZ_NH N ~ (1B) N
Rz Le A 30 882-Foreilzn countries R', RZ and R3 have, for example, the meanings listed above in group 1 under formula (IA).
Group 3 S
R
R~
SOZ _ NH N ~ (IC) N
RZ
R', RZ and R3 have, for example, the meanings listed above in group 1 under formula (IA).
Using, for example, 2,6-difluoro-phenyl isocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazole-3-thione as starting materials, the course of reaction in the process (a) according to the invention can be illustrated by the following equation:
s F F
I + H~N N,OCH3 ~ I O S
, w SOZ N_C_O N~ ~ ~ SO2' ~N~N~OCH3 N

C2Hs Using, for example, 2-methylthio-benzenesulphonamide and 2-chlorocarbonyl-4-dimethylamino-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-thion~s starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the following equation:
s SCH O ~ SCH
,N(CH3)2 3 O
I + CI N N ~ I
~ S02 NHZ N=C -HCI ~ SOZ' ~N N~N(CH3)2 N

_ Le A 30 882-Foreign countries Using, for example, N-methoxythiocarbonyl-2-methoxy-benzenesulphonamide and S-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of reaction in the process (c) according to the invention can be illustrated by the following eq'~zation:-S
OCH3 ~ OCH3 H~N N,CH3 I O S
S \ SOz N=C - HOCH3 ~ gOz\ ~N~N~CH3 OCzHs NH ~
H~N~OCH3 N OC H
zs S
Using, for example, 4-ethyl-S-ethylthio-2,4-dihydro-3H-1,2,4-triazole-3-thione and 2-bromo-benzenesulphonyl chloride and potassium thiocyanate as starting materials, the course of reaction in the process (d) according to the invention can be illustrated by the following equation:
Br S
SOZCI H ~ N ~ N' CzHs N
SC2Hs S S
+ KSCN
---~ SOz ~ N ~ N' CzHs KCI N
N
H SCzHs A general definition of the triazolin(ethi)ones to be used as starting materials in the processes (a), (c) and (d) according to the invention for preparing compounds of the formula (I) is given by the formula (II).
In the formula (II), Q', R' and Rz each preferably or in particular have that meaning 1 S which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or Br Le A 30 882-Foreign countries particularly preferable for Q', R'- and R2.
The triazolin(ethi)ones of the general formula (II) are known and/or can be prepared by methods known per se (cf. Arch. Pharm. 301 (1968), 827; loc. cit. 307 (1974), 889;
Bull. Soc. Chim. France 1962, 1365; loc. cit. 1975, 1191; Chem. Ber. 90 (1957), 909-921; loc. cit. 98 (1965), 3025-3099; loc. cit. 102 (1969), 755; J. Heterocycl.
Chem. 15 (1978), 237-240; J. Indian Chem. Soc. 6 (1929), 565; Liebigs Ann. Chem. 637 (1960), 135; Monatshefte Chemie 123 (1992), 257; Tetrahedron 32 (1976), 2347-2352;
Helv.
Chim. Acta 63 (1980), 841-859; J. Chem. Soc. C 1967, 746-751; loc. cit. 1970, 26-34;
J. Chem. Soc. Perkin I 1973, 2644; Fen Fak. Derg., Seri A (Ege Univ.) 7 (1984), 1-6 -quoted in Chem. Abstracts 101:90846m; EP-A 283876; EP-A 294666; EP-A 298371;
EP-A 301946; EP-A 305844; EP-A 341489; EP-A 362633; EP-A 370293; EP-A
391187; EP-A 398096; EP-A 398097; EP-A 399294; EP-A 415196; EP-A 422469;
EP-A 425948; EP-A 431291; EP-A 477646; EP-A 502307; EP-A 503437; EP-A
505819; EP-A 511569; EP-A 513621; DE-A 2336827; DE-A 3839206; DE-A 3916208;
DE-A 3916930; DD-P 64970; WO-A 93/04050; Preparation Examples).
A general definition of the sulphonyl iso(thio)cyanates also to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I) is given by the formula (III).
In the formula (III), QZ and R3 each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention as being preferable or particularly preferable for QZ and R3.
The starting materials of the formula (III) are known and/or can be prepared by methods known per se (cf. US-P 4127405, US-P 4169719, US-P 4371391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A
44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A
173312).

Le A 30 882-Foreign countries A general definition of the triazolin(ethi)one derivatives to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (IV). In the formula (IV), Q', Q'-, R' and R'- each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for Q', Q2, R' and RZ; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogeno- or nitro-phenoxy, and in particular represents methoxy, phenoxy or 4-nitro-phenoxy.
The starting materials of the formula (IV) have not been disclosed in the literature; as novel substances, they are also part of the subject matter of the present application.
The novel compounds of the general formula (IV) are obtained when triazolin(ethi)ones of the general formula (II) O
H~N~N,R II
( )~
Rz in which Q', R' and R'- are each as defined above, are reacted with (thio)carbonic acid derivatives of the general formula (IX) Z-CQz-Z' (IX) in which Z and QZ are each as defined above and Z' , represents halogen, alkoxy, aralkoxy or aryloxy, Le A 30 882-Foreign countries if appropriate in the presence of an acid acceptor, such as, for example, sodium hydroxide or potassium hydroxide, sodium t-butoxide or potassium t-butoxide, and if appropriate in the presence of a diluent, such as, for example, methylene chloride, tetrahydrofuran or dimethoxyethane and/or water, at temperatures between 0°C and 100°C.
A general definition of the sulphonamides also to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (V). In the formula (V), R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R3.
The starting materials of the formula (V) are known and/or can be prepared by methods known per se (cf. US-P 4127405, US-P 4169719, US-P 4371391, EP-A 7687, EP-A
13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A
44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A
173312).
A general definition of the sulphonamide'derivatives to be used as starting materials in the process (c) according to the invention for preparing compounds of the general formula (I) is given by the formula (VI). In the formula (VI), QZ and R3 each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for QZ and R3; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy; benzyloxy or phenoxy, and in particular represents methoxy or phenoxy.
The starting materials of the formula (VI) are known and/or can be prepared by methods known per se.
A general definition of the sulphonyl halides to be used as starting materials in the ,_ Le A 30 882-Foreign countries process (d) according to the invention for preparing compounds of the formula (I) is given by the formula (VII). In the formula (VII), R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable. or particularly preferable for R3;
X preferably represents fluorine, chlorine or bromine, and in particular represents chlorine.
The starting materials of the formula (VII) are known and/or can be prepared by methods known per se.
The processes (a), (b), (c) and (d) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents.
Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone;
esters such as methyl acetate and ethyl. acetate; nitriles, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention it is possible to employ all acid-binding agents which can.
customarily be used for such reactions. Preference is given to alkali metal hydroxides, for example sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alkoxides, such as sodium carbonate and potassium carbonate, sodium tent-butoxide and potassium tert-butoxide, and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, Le A 30 882-Foreign countries ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethyl-aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo-[2.2.2]-octane (DABCO).
The reaction temperatures in the processes (a), (b), (c) and (d) according to the invention can be varied within a relatively wide range. The reactions are in general carried out at temperatures of between -20°C and +150°C, preferably at temperatures between 0°C and +100°C.
The processes (a), (b), (c) and (d) according to the invention are generally carned out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.
For carrying out processes (a), (b), (c)' and (d) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carned out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Work-up in the case of the processes (a), (b), (c) and (d) according to the invention is in each case carried out by customary methds (cf. the Preparation Examples).
Salts of the compounds of the general formula (I) according to the invention can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then - if desired after prolonged stirring - be isolated by concentration or filtration with suction.
The active compounds according to the invention can be used as defoliants, desiccants, a.
Le A 30 882-Foreign countries haulm killers and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted.
Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledonous weeds of the enera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledonous crops of the enera~ Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledonous weeds of the enera~ Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,~ Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledonous crops of the general Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control of " 25 weeds, for example on industrial terrain and rail tracks, and on paths and squares with Le A 30 882-Foreign countries or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial crops, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective control of weeds in annual crops.
The compounds of the formula (I) according to the invention are preferably suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both pre-emergence and post-emergence.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable liquid solvents are in the main:
aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

Le A 30 882-Foreign countries Suitable solid carriers are:
for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates;
suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, ready-to-use formulations or tank mixes being possible.

- Le A 30 882-Foreign countries Possible components for the mixtures are known herbicides, for example anilides, such as diflufenican and propanil; arylcarboxylic acids, such as dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, such as chloridazon and norflurazon; carbamates, such as chlorpropham, desmedipharr~, phenmedipham and propham; chloroacetanilides, such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor;
dinitroanilines, such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, such as acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen;
areas, such as chlorotoluron, diuron, fluometuron, isproturon, linuron and methabenzthiazuron; hydroxylamines, such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitrites, such as bromoxynil, dichlobenil and ioxynil;
oxyacetamides, such as mefenacet; sulphonyl-areas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, inetsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine; triazinones, such as hexazinone, metamitron and metribuzin; others, such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, defenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary Le A 30 882-Foreign countries manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 10 g and 5 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the following examples.

Le A 30 882-Foreign countries _ ~3 _ Preparation Examples Example 1 O
S
CI \
S02,NH N N~CH3 N

(by process (a)) A mixture of 3.0 g (20.7 mmol) of 4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one, 4.8 g (20.7 mmol) of 3-chloro-phenylsulphonyl isothiocyanate, 0.3 g of triethylamine and 60 ml of acetonitrile is heated under reflux for 12 hours and then concentrated under, water pump vacuum. The residue is stirred with diethyl ether and the crystalline product is isolated by filtration under suction.
2.1 g (27% of theory) of 2-(3-chloro-phenylsulphonyl-aminothiocarbonyl)-4-methyl-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 141 °C
are obtained.
Example 2 S O
S02, ~N~N~CH3 NH
N

(by process (b)) A mixture of 3.2 g (12 mmol) of 5-methoxy-4-methyl-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 2.9 g (12 mmol) of 2-trifluoromethoxy-benzene-Le A 30 882-Foreign countries sulphonamide, 1.9 g (12.5 mmol) of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 30 ml. of dioxane is stirred at 20°C for 12 hours. The mixture is then diluted with methylene chloride and water and the pH is adjusted to 3 using 2N hydrochloric acid.
The organic phase is then separated off, dried with sodium sulphate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is crystallized by digestion with diethyl ether and the product is isolated by filtration under suction.
3.1 g (63% of theory) of 5-methoxy-4-methyl-2-(2-trifluoromethoxy-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 139°C are obtained.
Example 3 S O
S02,NH N N~CH3 N=-C

(by process (b)) At 20°C, 28.1 g (0.125 mol) of 2-trifluoromethyl-benzenesulphonamide and a solution of 19 g of 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) in 50 ml of acetonitrile are added in succession to a solution of 28.1 g (0.10 mol) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one in 300 ml of acetonitrile. The reaction mixture is stirred at 20°C until a clear solution is obtained.
The solution is then concentrated under water pump vacuum and the residue is admixed with water and methylene chloride (300 mI each) and acidified with 2N hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted once more with 100 ml of methylene chloride and the combined organic phases are dried with magnesium sulphate and filtered. The filtrate is concentrated under a water pump vacuum and the residue is crystallized from isopropanol.

Le A 30 882-Foreign countries 29.6 g (72% of theory) of 4-methyl-5-methylthio-2-(2-trifluoromethyl-phenylsulphonyl-aminothiocarbonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 154°C are obtained.
By the methods of Examples 1, 2 and 3 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for example, the compounds of the formula (I) listed in Table 1 below.
Q, R ~ ~ R~
S02,NH N N' (I) N=C

Le A 30 882-Foreign countries ..

Table 1: Examples of compounds of the formula (I) Ex. Q' Q'- R' R'- R3 Melti No.
point 4 O S CH3 OC3H, ~ OCF3 94 5 S O CH3 C~HS / C F3 126 i i i / \
COOCZHS

10 O S CH3 SCH3 ~ cF3 194 I

11 O S CH3 SCH3 g~ 143 i i Le A 30 882-Foreign countries .

Table l: (continued) Ex. Q' Q'- R' R'- R3 Melting No. point (°C) ~ 3 16 O S CH3 SCH3 ~ cF3 125 i w F

i CI

i CI

Le A 30 882-Foreign countries - Table l: (continued) Ex. Q' QZ R' R' R3 Melting No. point (°C) 20 O S CH3 SCH3 sc H 157 zs 21 O S CH3 SCH3 ~ soZc2H5 171 I

23 O S CH3 SCH3 oC2H5 139 i 24 O S CH3 SCH3 c1 134 i CHz CI

i CHZ

27 O S CH3 C2H5 ~ CF3 126 \

Le A 30 882-Foreign countries Table l: (continued) Ex. Q' Q'- R' RZ R3 Melting No. point (°C) 29 O S CH3 CZHS ~ CH3 128 30 O S CH3 C~HS OCF3 103 i 31 O S CH3 C2H5 ~ cF, 92 32 O S CH3 CZHS ~ ~ cF3 111 33 O S CH3 CZHS ~ CI 141 w G
34 O S CH3 OCzHS CH 142 i 36 O S CH3 OCZHS ~ cF3 110 \ I
37 O S CH3 OCZHS ~ ~ cF, 131 \ I

Le A 30 882-Foreign countries <-Table l: (continued) Ex. Q' QZ R' RZ R3 Melting No. point (°C) i \
CI

i F

i CI

ss 42 O S CH3 OCZHS ~ sC2H5 123 43 O S CH3 OCZHS ~ OCH3 127 \

45 O S -(CHZ)5- ~ OCF3 128 i Le A 30 882-Foreign countries ' Table 1: (continued) Ex. Q' QZ R' R'- R3 Melting No. point (°C) 46 O S CH3 OOHS ~ OCHFZ 147 47 O S OCzHS OCZHS CF3 114 i i 49 O S N(CH3)~ C3H,-n CF3 113 50 O S N(CH3), C3H., n , OCF3 114 w 51 O S ~ OC3H~ i CF 74 52 O S ~ OC3H~ i OCF3 119 i I
53 O S ~ N(CH3)~ ~ CF3 131 54 O S ~ N(CH3)Z ~ OCF3 132 Le A 30 882-Foreign countries Table 1: (continued) Ex. Q' Q'- R' R'- R' Melting No. point (°C) 56 O S ~ ~ OCF3 124 57 O S ~ SC,HS CF 123 58 O S ~ SC,HS ~ OCF3 125 \
61 O S OCH3 SCzHs CF 121 62 O S OCH3 SC,HS OCF 122 ~ \ 3 \

Le A 30 882-Foreign countries ' Table 1: (continued) Ex. Q' QZ R' R'- R3 Melting No. point (°C) 64 O S CH3 CH; OCF3 122 i 65 O S CH3 CH3 ~ OCHFz 113 I

67 O S CH3 C3H~ n CF3 112 i \
68 O S CH3 C3H~ n ~ OCHFZ 112 I
w 69 O S CH3 C3H; i CF3 119 i \
70 O S CH3 C3H; i OCF 101 71 O S CH3 C3H~ i ~ OCHFz 118 \

Le A 30 882-Foreign countries ' Table 1: (continued) Ex. Q' Q'- R' R'- R3 Melting No. point (°C) 74 O S CH3 CHZOCH3 OCHFz 106 /v I
75 O S CH; SCZHS CF 129 i 77 O S CH3 SC~HS ~ OCHFZ 135 78 O S CH3 OCH3 ~ OCHFz 131 \

i 80 O S CZHS OCZHS OCHFz 85 I
81 O S CH3 OC3H~ n CF 108 82 O S CH3 OC3H, n CF3 122 j \

Le A 30 882-Foreign countries r - Table 1: (continued) Ex. Q' Q'- R' R'- R' Melting No. point (°C) 83 O S CH; OC3H~ i OCF3 119 i 84 O S CH3 OC3H~-i OCHF 130 85 O S CZHS OCH3 cF3 123 i \
86 O S CZHS OCH3 ~ OCHFz 132 \
87 O S OCzHs CZHS OCF3 109 i 88 O S OCZHS CzHs ~ OCHFZ 105 89 O S CH3 Br ~F3 126 i \
90 O S CH3 Br OCF 115 91 O S CH3 Br ~ oCHFz 113 \

Le A 30 882-Forei.~n countries Table 1: (continued) Ex. Q' Q'- R' R' R3 Melting No. point (C) 92 O S ~ Br oF3 113 i w 93 O S ~ Br oCF3 107 i I

94 O S ~ Br ocHFz 103 I

95 O S ~ OOHS cF3 117 96 O S ~ OCZHS ocF3 105 w 97 O S ~ OCZHS ~ OCHFZ 90 98 O S ~ CHZOCH3 cF3 106 w 99 O S ~ CHZOCH3 oCF3 119 i 100 O S ~ CHZOCH3 ~ OCHFZ 110 Le A 30 882-Foreign countries Table 1: (continued) Ex. Q' QZ R' R'- R3 Melting No. point (°C) 101 O S CH3 C,HS , SOZN(CH3)z 119 102 O S CH3 CZHS sc H 126 Zs w 103 O S CH3 C2H5 ~ soZc2H5 122 104 O S CH3 CZHS ocH3 127 i , 105 O S CH3 CZHS oczHS 129 i 106 O S CH3 OOHS / So2N(CH~)z 137 \I
107 O S CH3 OC,HS so2c2H5 127 w 109 O S CH3 C~HS F 141 i I
F

Le A 30 882-Foreign countries r Table 1: (continued) Ex. Q' QZ R' R'- R3 Melting No. point (°C) I
112 O S CH3 C,HS F 128 -i w 113 O S CH3 CZHS ci 115 /
\
114. O S CH3 CZHS ci 108 I
115 O S CH3 CZHS g~ 129 /
I

/
117 O S CH3 OCzHS F 130 /

Le A 30 882-Foreign countries - Table 1: (continued) Ex. Q' Q'- R' R' R3 Melting No. point (°C) 118 O S CH3 OC,HS ~~ 135 i 119 O S CH3 OCZHS ci 145 i 120 O S CH3 OCZHS g,. 128 i I

i 123 O S CH3 CzHS ocF3 115 i i CHZ-125 O S CH3 OCZHS ocF3 132 i I
CHZ

Le A 30 882-Foreign countries Table 1: (continued) Ex. Q' QZ R' R'- R3 Melting No. point (°C) 126 O S CH3 SCH3 cF3 138 i I
CHZ
127 O S ~ OCZHS cH3 137 \
128 O S ~ OCZHS scH3 105 \
129 O S ~ OC,HS off 122 i \

i I
\
131 O S OCZHS CZHS off 97 i \
132 O S ~ Br scH3 132 i \
133 O S OCZHS C2H5 cH

134 O S OCZHS CzHS scH3 11~
i Le A 30 882-Foreign countries Table l: (continued) ' Ex. Q' QZ R' RZ R3 Melting No. point (°C) 135 O S ~ Br cH3 118 i \
136 O S CH3 CHZOCH3 ~ scH3 100 \
137 O S ~ Br i \
138 O S CH3 CHZOCH3 cH

139 O S CH3 OCHZCF3 cF 73 140 O S CH3 OCHZCF3 ocF3 107 \
141 O S CH3 OCHzCF3 OCHF 116 \ I
142 O S CH3 OC3H,-n ocHF2 i Le A 30 882-Foreign countries Table 1: (continued) ' Ex. Q' Q'- R' R'- R3 Melting No. point (°C) 143 O S OCH,HS CZHS OCF3 i w i w CH,-Ci 146 O S OCH3 C3H; n OCF 98 147 O S CH3 SCH3 sc2H5 208 I
(Na salt) (Na salt) I

(Na salt) I
150 O S CH3 OCH3 oCF 216 3 (Na salt) I
I' I O S CH3 OCZHs , oCHFz 21 I
(Na salt) Le A 30 882-Forei n countries Table 1: (continued) Ex. Q' Q'- R' R'- R3 Melting No. point (°C) 152 O S CH3 OC3H~ n OCF 217 (Na salt) i CHZ-CI
154 O S -CHZCH=CHZ OCZHS CH 130 155 O S -CHZCH=CHZ OCZHS oCF 84 156 O S -CHZCH=CHI OCZHS CF 85 157 O S OCZHS ~ OCHF2 205 ~ (Na salt) Br OCHFZ 212 (Na salt) w Br OCF3 220 (Na salt) Le A 30 882-Foreign countries Table l: (continued) Ex. Q' Q'- R' R'- R3 Melting No. point (C) 160 O S -a Br ~ 150 I (Na salt) 161 O S CH3 -CH20CH3 oCF 205 (Na salt) (Na salt) w 163 O S ~ OCZHS ~ osoZcH3 128 164 O S OCZHS C2H5 ~ oso2cH3 120 Le A 30 882-Foreign countries Starting materials of the formula (II):
Example (II-1) O
H~N~N~O-C2H5 N=-C

A mixture of 4.0 g (20 mmol) of the potassium salt of 4-ethoxy-5-mercapto-2,4-S dihydro-3H-1,2,4-triazol-3-one, 4.3 g (30 mmol) of methyl iodide and 50 ml of methanol is stirred at 20°C for 16 hours and then concentrated. The residue is extracted with methylene chloride/water and the organic phase is separated off, dried with magnesium sulphate and filtered. The filtrate is concentrated, the residue is digested with diethyl ether and the crystalline product is isolated by filtration under suction.
1.8 g (51%6+1 of theory) of 4-ethoxy-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 99°C are obtained.
By the methods of Example (II-1) and/or by other known methods (cf. the publications mentioned above), it is also possible to prepare, for example, the compounds of the formula (II) below:
4-methyl-, 4,5-dimethyl-, 4-methyl-5-ethyl-, 4-methyl-5-n-propyl-, 4-methyl-5-i-propyl-, 4-methyl-5-n-butyl-, 4-methyl-5-phenoxy-, 4-methyl-5-methylthio-, 4-methyl-5-ethylthio-, 4-methyl-5-n-propylthio-, 4-methyl-5-i-propylthio-, 4-methyl-5-allylthio-, 4-methyl-5-propargylthio-, 4-methyl-5-cyclopropyl-, 4-methyl-5-chloro-, 4-methyl-5-bromo-, 4-methyl-5-methoxy-, 4-methyl-5-ethoxy-, 4-methyl-5-n-propoxy-, 4-methyl-5-i-propoxy-, 4-methyl-5-n-butoxy-, 4-methyl-5-cyclopropylmethoxy-, 4-methyl-5-cyclopropylthio-, 4-methyl-5-trifluoroethoxy-,4-methyl-5-dimethylamino-and 4-methyl-5-methylamino- -2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H-1,2,4-triazole-3-thione;

Le A 30 882-Foreign countries 4-ethyl-, 4,5-diethyl-, 4-ethyl-5-methyl-, 4-ethyl-S-n-propyl-, 4-ethyl-5-i-propyl-, 4-ethyl-5-n-butyl-, 4-ethyl-5-phenoxy-, 4-ethyl-5-methylthio-, 4-ethyl-5-ethylthio-, 4-ethyl-5-n-propylthio-, 4-ethyl-5-i-propylthio-, 4-ethyl-S-allylthio-, 4-ethyl-5-propargylthio-, 4-ethyl-5-cyclopropyl-, 4-ethyl-5-chloro-, 4-ethyl-5-bromo-, 4-ethyl-5-methoxy-, 4-ethyl-5-ethoxy-, 4-ethyl-5-n-propoxy-, 4-ethyl-5-i-propoxy-, 4-ethyl-5-n-butoxy-, 4-ethyl-5-cyclopropylmethoxy-, 4-ethyl-5-cyclopropylthio-, 4-ethyl-5-trifluoroethoxy-,4-ethyl-5-dimethylamino-and 4-ethyl-5-methylamino--2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H-1,2,4-triazole-3-thione;
4-cyclopropyl-5-methyl-, 4-cyclopropyl-5-ethyl-, 4-cyclopropyl-5-n-propyl-, 4-cyclopropyl-5-i-propyl-, 4-cyclopropyl-5-n-butyl-, 4-cyclopropyl-5-phenoxy , 4-cyclopropyl-5-methylthio-, 4-cyclopropyl-5-ethylthio-, 4-cyclopropyl-5-n-propylthio-, 4-cyclopropyl-5-i-propylthio-,4-cyclopropyl-5-allylthio-,4-cyclopropyl-5-propargylthio-, 4-cyclopropyl-5-cyclopropyl-, 4-cyclopropyl-5-chloro-, 4-cyclopropyl-5-bromo-, 4-cyclopropyl-5-methoxy-, 4-cyclopropyl-5-ethoxy-, 4-cyclopropyl-5-n-propoxy-, 4-cyclopropyl-S-i-propoxy-, 4-cyclopropyl-5-n-butoxy-, 4-cyclopropyl-5-cyclopropylmethoxy-, 4-cyclopropyl-5-cyclopropylthio-, 4-cyclopropyl-S-trifluoroethoxy-, 4-cyclopropyl-5-dimethylamino- and 4-cyclopropyl-5-methylamino--2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H-1,2,4-triazole-3-thione;
4-methoxy-, 4,5-dimethoxy-, 4-methoxy-5-methyl-, 4-methoxy-5-ethyl-, 4-methoxy-5-n propyl-, 4-methoxy-5-i-propyl-, 4-methoxy-5-n-butyl-, 4-methoxy-5-phenoxy-, 4-methoxy-5-methylthio-, 4-methoxy-5-ethylthio-, 4-methoxy-5-n-propylthio-, 4-methoxy-5-i-propylthio-, 4-methoxy-5-allylthio-, 4-methoxy-5-propargylthio-, 4-methoxy-5-cyclopropyl-, 4-methoxy-5-chloro-, 4-methoxy-5-bromo-, 4-methoxy-5 ethoxy-, 4-methoxy-5-n-propoxy-, 4-methoxy-5-i-propoxy-, 4-methoxy-5-n-butoxy-, 4-methoxy-5-cyclopropylmethoxy-, 4-methoxy-5-cyclopropylthio-, 4-methoxy-5-trifluoroethoxy-, 4-methoxy-5-dimethylamino- and 4-methoxy-5-methylamino-2,4-dihydro-3H-1,2,4-triazol-3-one and -2;4-dihydro-3H-1,2,4-triazole-3-thione;
4-ethoxy-, 4,5-diethoxy-, 4-ethoxy-5-methyl-, 4-ethoxy-5-ethyl-, 4-ethoxy-5-n-propyl-, 4-ethoxy-5-i-propyl-, 4-ethoxy-5-n-butyl-, 4-ethoxy-5-phenoxy-, 4-ethoxy-5-methylthio-, 4-ethoxy-5-ethylthio-, 4-ethoxy-5-n-propylthio-, 4-ethoxy-5-i-propylthio-, 4-ethoxy-5-allylthio-, 4-ethoxy-5-propargylthio-, 4-ethoxy-5-cyclopropyl-, 4-ethoxy-5-chloro-, 4-ethoxy-5-bromo-, 4-ethoxy-5-methoxy-, 4-ethoxy-5-n-propoxy-, 4-ethoxy-5-i-Le A 30 882-Foreign countries propoxy-, 4-ethoxy-5-n-butoxy-, 4-ethoxy-5-cyclopropylmethoxy-, 4-ethoxy-S-cyclopropylthio-, 4-ethoxy-5-trifluoroethoxy-, 4-ethoxy-5-dimethylamino- and 4-ethoxy-5-methylamino- -2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H-1,2,4-triazole-3-thione;
4-amino-, 4-amino-S-methyl-, 4-amino-5-ethyl-, 4-amino-5-n-propyl-, 4-amino-5-i-propyl-, 4-amino-5-n-butyl-, 4-amino-5-phenoxy-, 4-amino-5-methylthio-, 4-amino-5-ethylthio-, 4-amino-5-n-propylthio-, 4-amino-S-i-propylthio-, 4-amino-5-allylthio-, 4-amino-5-propargylthio-, 4-amino-5-cyclopropyl-, 4-amino-5-chloro-, 4-amino-5-bromo-, 4-amino-5-methoxy-, 4-amino-5-ethoxy-, 4-amino-5-n-propoxy-, 4-amino-5-i-propoxy-, 4-amino-5-n-butoxy-, 4-amino-5-cyclopropylmetlloxy-, 4-amino-5-cyclo-propylthio-, 4-amino-5-trifluoroethoxy-, 4-amino-5-dimethylamino- and 4-amino-methylamino- -2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3H-1,2,4-triazole-3-thione;
4-methylamino-, 4-methylamino-5-methyl-,4-methylamino-5-ethyl-,4-methylamino-5-n propyl-, 4-methylamino-5-i-propyl-, 4-methylamino-5-n-butyl-, 4-methylamino-5 phenoxy-, 4-methylamino-5-methylthio-, 4-methylamino-5-ethylthio-, 4-methylamino-5 n-propylthio-, 4-methylamino-S-i-propylthio-, 4-methylamino-S-allylthio-, 4-methylamino-S-propargylthio-, 4-methylamino-5-cyclopropyl-, 4-methylamino-5 chloro-, 4-methylamino-5-bromo-, 4-methylamino-5-methoxy-, 4-methylamino-5 ethoxy-, 4-methylamino-5-n-propoxy-,4-methylamino-5-i-propoxy-,4-methylamino-5-n-butoxy-, 4-methylamino-5-cyclopropylmethoxy-, 4-methylamino-5-cyclopropylthio-, 4-methylamino-5-trifluoroethoxy-, 4-methylamino-5-dimethylamino- and 4-methylamino-5-methylamino- -2,4-dihydro-3H-1,2,4-triazol-3-one and -2,4-dihydro-3 H-1,2,4-triazole-3-thione;
4-dimethylamino-, 4-dimethylamino-5-methyl-, 4-dimethylamino-5-ethyl-, 4-dimethylamino-5-n-propyl-,4-dimethylamino-5-i-propyl-,4-dimethylamino-5-n-butyl-, 4-dimethylamino-5-phenoxy-, 4-dimethylamino-5-methylthio-, 4-dimethylamino-5-ethylthio-, 4-dimethylamino-5-n-propylthio-, 4-dimethylamino-5-i-propylthio-, 4-dimethylamino-5-allylthio-, 4-dimethylamino-5-propargylthio-, 4-dimethylamino-5-cyclopropyl-, 4-dimethylamino-5-chloro-,4-dimethylamino-5-bromo-,4-dimethylamino-5-methoxy-, 4-dimethylamino-5-ethoxy-, 4-dimethylamino-5-n-propoxy-, 4-dimethylamino-5-i-propoxy-, 4-dimethylamino-5-n-butoxy-, 4-dimethylamino-5-Le A 30 882-Foreign countries cyclopropylmethoxy-, 4-dimethylamino-5-cyclopropylthio-, 4-dimethylamino-5-trifluoroethoxy-, 4-dimethylamino-5-dimethylamino- and 4-dimethylamino-5-methylamino- -2,4-dihydro-3H-1,2,4-triazol-3-one and 2,4-dihydro-3H-1,2,4-triazole-3-thione.
Starting materials of the formula (IV)' Example (IV-1) S O
W ~N~N~CH3 O
N

At 20°C, a solution of 15.0 g (103 mmol) of 4-methyl-S-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one in 120 ml of methylene chloride is admixed with a solution of 4.6 g of sodium hydroxide and 0.5 g of tetrabutylammonium bromide in 120 ml of water. A
solution of 19.6 g (114 mmol) of O-phenyl chlorothioformate in 100 ml of methylene chloride is then added dropwise to this mixture at 20°C, and the reaction mixture is stirred at 20°C for a further 12 hours. The crystalline product is isolated by filtration under suction.
25.6 g (88% of theory) of 4-methyl-5-methylthio-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 242°C are obtained.
Example (IV-2) t S O
w ~N~N~CH3 O
N
OCZHS
At 20°C, a solution of 29.6 g (206 mmol) of 4-methyl-5-ethoxy-2,4-dihydro-3H-1,2,4-Le A 30 882-Foreign countries' triazol-3-one in 240 ml of methylene chloride is admixed with a solution of 9.2 g of sodium hydroxide and 1 g of tetrabutylammonium bromide in 240 ml of water. A
solution of 39.2 g (228 mmol) of O-phenyl chlorothioformate in 200 ml of methylene chloride is then added dropwise to this mixture at 20°C, and the reaction mixture is stirred at 20°C for a further 12 hours. The organic phase is then separated off and the aqueous phase is extracted once more with 100 ml of methylene chloride. The combined organic phases are washed with 200 m1 of water, dried with magnesium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is stirred with diethyl ether and the crystalline product is isolated by filtration under suction.
44.3 g (77% of theory) of 4-methyl-5-ethoxy-2-phenoxythiocarbonyl-2,4-dihydro-1,2,4-triazol-3-one of melting point 123°C are obtained.
By the methods of Examples (IV-1) and (IV-2), it is also possible to prepare, for example, the compounds of the formula (IV) listed in Table 2 below.

c-X
Le A 30 882-Foreign countries ~

_ 1 ~N
N~R

IV
N () Tabl'.e a (IV) 2: Examples of the compounds of the formul Ex., Q' QZ R' RZ Z Melting No. point (C) IV-~3 O S CH3 C,HS OC6H5 136 IV-~I O S NHZ CH3 OC6H5 177 IV-5 O S NHz N(CH3)z OC6H5 161 IV-6 O S / ~~CgH9 n N(CH3)2 OC6H5 92 IV-7 O S NHZ OCH3. OC6H5 158 IV-8 O S CH3 OC3H~ n OC6H5 90 IV-10 O S -(CH2)5- OC6H5 153 w Le A 30 882-Foreign countries Table 2: (continued) Ex. Q ' QZ R' R'- Z Melting No. point (°C) IV-11 O S ~ OCzHS OC6H5 148 IV-16 O S N(CH3)2 C3H~-n OC6H5 58 ~

IV-17 O S OC3H~ i OC6H5 89 IV-18 O S ~ N(CH3)z OC6H5 154 Le A 30 882-Foreign countries Table 2: (continued) Ex.- Q' QZ R' R.'- Z Melting No. point (°C) IV-19 O S ~ ~ OC6H5 144 IV-20 O S ~ S-CZHS OC6H5 124 IV-21 O S CH3 OC3H,-i OC6H5 108 IV-24 , O S CH3 Br OC6H5 211 IV-26 O S OCH3 C3H, n OC6H5 oil Le A 30 882-Foreign countries Table 2: (continued) Ex.- Q' Q'- R' RZ Z Melting No. point (°C) IV-27 O S ~ Br OC6H5 172 IV-28 O S ~ CHZOCH3 OC6H5 74 IV-29 O S CzHs OCZHS OC6H5 89 IV-31 O S CH3 C3H~-n OC6H5 67 IV-32 O S CH3 C3H~ i OC6H5 96 IV-35 O S CHZ CH=CHZ OCZHS OC6H5 Le A 30 882-Foreign countries Use Examples:
Example A
Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After 24 hours, the soil is watered with the preparation of the active compound. It is advantageous to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control) 100% = total destruction In this test, the compounds according to Preparation Examples 3, 23, 27 and 28, for example, exhibit a very strong action against weeds, while some of them are very well tolerated by crops, such as cotton.

Le A 30 882-Foreign countries Table A: Pre-emergence testlgreenhouse Appli-CottonEchinoPoa SetariaPortu-Sola-Active compound cation chloa laca num rate (glha) S O

~CH ~0 0 95 95 90 95 95 S02, a N

~
NH
N

(3) OCzHs S O

soz, N ~ N ~CH3 60 0 80 95 90 70 90 NH
N

(23) S O

sot, N~N--~H3 60 0 95 95 95 90 90 ~

N
~
N=

C2Hs (27) S O

sot, N ~ N,~H3 60 0 95 95 95 95 95 NH
N

(28) ,_ Le A 30 882-ForeiPn countries Example B
Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are employed in 1000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.
The figures denote:
0% = no action (like untreated control) 100% = total destruction In this test, the compounds of Preparation Examples 3, 15 and 28, for example, exhibit a very strong action against weeds, while being well tolerated by crops, such as wheat.

Le A 30 882-Fore~n countries Table B: Post-emergence test/greenhouse Appli- Wheat Amaran- Helia Sola- Xanthium Active compound cation thus nthus num rate (g/ha) S O
so2,N ~N~N~CHa 60 5 95 100 90 95 N

(3) S O
sot, N~N~oH3 60 0 85 95 85 70 Nf~ ~
AI~I
~V

(15) S O
sot, N~N~cH3 60 10 95 100 99 90 NH
N
OCzHS
(28)

Claims (9)

CLAIMS:

1. A compound of the general formula (I) or a salt thereof:
wherein:
R1 represents: (i) H, hydroxyl, amino, C2-C10-alkylideneamino, C3-C6-alkenyloxy or di- (C1-C4-alkyl) -amino, (ii) optionally F-, Cl-, Br-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkyl, (iii) optionally F-, Cl-, Br- or a combination thereof-substituted C2-C6-alkenyl or C2-C6-alkinyl, (iv) optionally F-, Cl-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-alkyl amino or C1-C6-alkanoylamino, (v) optionally F-, Cl-, Br-, cyano-, C1-C4-alkyl- or a combination thereof-substituted C3-C6-cycloalkyl, C3-C6-cycloalkylamino or C3-C6-cycloalkyl-C1-C4-alkyl, or (vi) optionally F-, Cl-, Br-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- or a combination thereof-substituted phenyl or phenyl-C1-C4-alkyl;
R2 represents: (i) H, hydroxyl, mercapto, amino, F, Cl, Br, I, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3-C6-alkenylthio, C3-C6-alkinylthio, C3-C6-alkenylamino, C3-C6-alkinylamino or di-(C1-C4-alkyl)-amino, (ii) as defined for R1, (iii) as defined for R1, (iv) optionally F-, Cl-, cyano-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylamino or C1-C6-alkanoylamino, (v) optionally methyl-, ethyl- or a combination thereof-substituted aziridino, pyrrolidino, piperidino or morpholino, (vi) optionally F-, Cl-, Br-, cyano-, C1-C4-alkyl- or a combination thereof-substituted C3-C6-cycloalkyl, C5-C6-cycloalkenyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, C3-C6-cycloalkylamino, C3-C6-cycloalkyl-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkoxy, C3-C6-cycloalkyl-C1-C4-alkylthio or C3-C6-cycloalkyl-C1-C4-alkylamino, or (vii) optionally F-, Cl-, Br-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- or a combination thereof-substituted phenyl, phenyl-C1-C4-alkyl, phenoxy, phenyl-C1-C4-alkoxy, phenylthio, phenyl-C1-C4-alkylthio, phenylamino or phenyl-C1-C4-alkyl amino; or R1 and R2 together represent optionally branched alkanediyl having 3 to 11 carbon atoms; and R3 represents:
wherein:
R4 and R5 are identical or different and each represent: (i) H, F, Cl, Br, I, nitro, C3-C6-alkinyloxy, C3-C6-alkinylthio, phenyl, phenoxy, C1-C4-alkyl-carbonylamino, C1-C4-alkoxy-carbonylamino, C1-C4-alkylamino-carbonyl-amino, di-(C1-C4-alkyl)-amino-carbonylamino, trimethylsilyl, thiazolinyl, C1-C4-alkyl-sulphonyloxy or di- (C1-C4-alkyl) -aminosulphonylamino, (ii) optionally F-, Cl-, Br-, cyano-, carboxyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylamino-carbonyl-, di- (C1-C4-alkyl) -amino-carbonyl-, hydroxyl-, C1-C4-alkoxy-, formyloxy-, C1-C4-alkyl-carbonyloxy-, C1-C4-alkoxy-carbonyloxy-, C1-C4-alkylamino-carbonyloxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, di- (C1-C4-alkyl)-aminosulphonyl-, C3-C6-cycloalkyl- or phenyl-substituted, C1-C6-alkyl, (iii) optionally F-, Cl-, Br-, cyano-, C1-C4-alkoxy-carbonyl-, carboxyl- or phenyl-substituted C2-C6-alkenyl or C2-C6-alkinyl, (iv) optionally F-, Cl-, Br, cyano-, carboxyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted C1-C4-alkoxy, (v) optionally F-, Cl-, Br, cyano-, carboxyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted C1-C4-alkylthio, (vi) optionally F-, Cl-, Br-, cyano- or C1-C4-alkoxy-carbonyl-substituted C2-C6-alkenyloxy, (vii) optionally F-, Cl-, Br-, cyano-, nitro-, C1-C3-alkylthio- or C1-C4-alkoxy-carbonyl-substituted C2-C6-alkenylthio, or (viii) -S(O)p-R6, -CO-R8 or -CH=N-R9, wherein:
p represents 1 or 2, R6 represents: (i) optionally F-, Cl-, Br-, cyano-or C1-C4-alkoxy-carbonyl-substituted C1-C4-alkyl, (ii) C3-C6-alkenyl, C3-C6-alkinyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkylamino, C1-C4-alkyl amino, di-(C1-C4-alkyl)-amino or phenyl, or (iii) -NHOR7, wherein:
R7 represents: (i) optionally F-, Cl-, cyano-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkylamino-carbonyl- or di-(C1-C4-alkyl)-amino-carbonyl-substituted C1-C12-alkyl, (ii) optionally F-, Cl- or Br-substituted C3-C6-alkenyl, (iii) optionally F-, Cl-, nitro-, cyano-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C3-C6-alkinyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl or phenyl-C1-C2-alkyl, (iv) benzhydryl, or (v) optionally F-, C1-, nitro-, cyano-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy-, C1-C2-fluoroalkoxy-, C1-C4-alkylthio-, trifluoromethylthio- or C1-C4-alkoxy-carbonyl-substituted phenyl, R8 represents: (i) H, or (ii) optionally F-, Cl- or a combination thereof-substituted, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C1-C4-alkylthio, C1-C4-alkyl amino, C1-C4-alkoxyamino, C1-C4-alkoxy-C1-C4-alkyl-amino or di- (C1-C4-alkyl) -amino, and R9 represents: (i) optionally F-, Cl-, cyano-, carboxyl-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted C1-C6-alkyl, (ii) optionally F- or Cl-substituted benzyl, C3-C6-alkenyl or C3-C6-alkinyl, (iii) optionally F-, Cl-, Br-, C1-C4-alkyl-, C1-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, (iv) optionally F-, Cl- or a combination thereof-substituted C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or benzyloxy, (v) amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C1-C4-alkyl-carbonyl-amino, C1-C4-alkoxy-carbonylamino or C1-C4-alkyl-sulphonylamino, or (vi) optionally F-, Cl-, Br- or methyl-substituted phenylsulphonylamino;
wherein:
R10 represents H or C1-C4-alkyl, and R11 and R12 are identical or different and each represent: (i) H, F, Cl, Br, nitro, cyano, carboxyl, C1-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C1-C4-alkylsulphonyl or di-(C1-C4-alkyl)-aminosulphonyl, or (ii) optionally F-, Cl- or a combination thereof-substituted C1-C4-alkyl or C1-C4-alkoxy;

wherein:
R13 and R19 are identical or different and each represent: (i) H, F, Cl, Br, nitro or cyano, or (ii) as defined for R11 and R12;
wherein:
R15 and R16 are identical or different and each represent: (i) H, F, Cl, Br, nitro, cyano, aminosulphonyl, mono-(C1-C4-alkyl)-aminosulphonyl, di-(C1-C4-alkyl)-aminosulphonyl, C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl, or (ii) optionally F-, Cl- or a combination thereof-substituted C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl;
wherein:
R17 and R18 are identical or different and each represent: (i) H, F, Cl, Br or di-(C1-C4-alkyl)-aminosulphonyl, or (ii) as defined for R15 and R16 wherein:
R19 and R20 are identical or different and each represent: (i) H, F, Cl, Br, cyano, nitro, di-(C1-C4-alkyl)-amino-sulphonyl, C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl, or (ii) as defined for R15 and R16, and A represents O, S or N-Z1, wherein:
Z1 represents: (i) H, C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl or di-(C1-C4-alkyl)-amino-carbonyl, (ii) optionally F-, Cl-, Br or cyano-substituted C1-C4-alkyl, or (iii) optionally F-, Cl-, Br- or nitro-substituted C3-C6-cycloalkyl, benzyl or phenyl;
wherein:
R21 and R22 are identical or different and each represent H, C1-C4-alkyl, a halogen atom, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, and Y1 represents S or N-R23, wherein R23 represents H
or C1-C4-alkyl;
wherein:
R24 represents H, C1-C4-alkyl, benzyl, pyridyl, quinolinyl or phenyl, R25 represents: (i) H, a halogen atom, cyano, nitro, dioxolanyl or C1-C4-alkoxy-carbonyl, or (ii) as defined for R11 and R12, and R26 represents H, a halogen atom or C1-C4-alkyl; or

2. A compound of the general formula (I) according to claim 1, wherein the salt is the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di- (C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-ammonium, tetra- (C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, C5- or C6-cycloalkyl-ammonium or di-(C1-C2-alkyl) -benzyl-ammonium salt thereof.

3. A compound of the general formula (I) or a salt thereof according to claim 1 or 2, wherein:
R1 represents: (i) H, hydroxyl, amino, C3-C8-alkylideneamino, propenyloxy, butenyloxy, dimethylamino or diethylamino, (ii) optionally F-, Cl-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, (iii) optionally F-, Cl- or Br-substituted propenyl, butenyl, propinyl or butinyl, (iv) optionally F-, Cl-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, or n-, i-, s- or t-butylamino, (v) optionally F-, Cl-, methyl-, ethyl- or a combination thereof-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or (vi) optionally F-, Cl-, methyl-, trifluoromethyl-, methoxy-or a combination thereof-substituted phenyl or benzyl;

R2 represents: (i) H, hydroxyl, mercapto, amino, F, Cl, Br, propenyloxy, butenyloxy, propinyloxy, butinyloxy, propenylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino, butinylamino, dimethylamino, diethylamino or dipropylamino, (ii) optionally F-, Cl-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, (iii) optionally F-, Cl- or Br-substituted propenyl, butenyl, propinyl or butinyl, (iv) optionally F-, Cl-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n-or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, or n-, i-, s- or t-butylamino, (vi) optionally F-, Cl-, methyl-, ethyl- or a combination thereof-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or (vii) optionally F-, Cl-, methyl-, trifluoromethyl-, methoxy- or a combination thereof-substituted phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino; or R1 and R2 together are as defined in claim 1; and R3 represents:

wherein:
R4 represents: (i) F, Cl or Br, (ii) optionally F-, Cl- or a combination thereof-substituted methyl, ethyl, or n- or i-propyl, (iii) optionally F-, Cl-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl or phenoxy, or (iv) optionally F-, Cl-, methoxy- or ethoxy-substituted methoxycarbonyl, ethoxycarbonyl, or n- or i-propoxycarbonyl, and R5 represents H, methyl, ethyl, F, Cl or Br;
wherein:
R10 and R12 represent H, and R11 represents F, Cl, Br, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxy-carbonyl, ethoxycarbonyl, methylsulphonyl or dimethylamino-sulphonyl;
wherein R represents methyl, ethyl, n- or i-propyl; or wherein:
R29 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, R25 represents H, F, Cl or Br, and R26 represents F, Cl, Br, methoxycarbonyl or ethoxycarbonyl.

4. A process for preparing a compound of the general formula (I) and a salt thereof according to any one of claims 1 to 3, comprising (a) reacting, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, a compound of the general formula (II):
wherein R1 and R2 are each as defined in claim 1 or 3, with a compound of the general formula (III):
R3-SO2-N=C=S (III) wherein R3 is as defined in claim 1 or 3; or (b) reacting, optionally in the presence of an acid acceptor and optionally in the presence of a diluent, a compound of the general formula (IV):
wherein R1 and R2 are each as defined in claim 1 or 3, and Z
represents a halogen atom, alkoxy, aryloxy or arylalkoxy, with a sulphonamide of the general formula (V):
R3-SO2-NH2 (V) wherein R3 is as defined in claim 1 or 3; or (c) reacting, optionally in the presence of an acid acceptor and optionally in the presence of a diluent, a compound of the general formula (II) as defined in step (a) with a compound of the general formula (VI):
R3-SO2-NH-CS-Z (VI) wherein R3 is as defined in claim 1 or 3, and Z is as defined in step (b); or (d) reacting, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, a compound of the general formula (II) as defined in step (a) with a sulphonyl halide of the general formula (VII):
R3-SO2-X (VII) wherein R3 is as defined in claim 1 or 3, and X represents a halogen atom, and a compound of the general formula (VIII):

MS-CN (VIII) wherein M represents an alkali metal or an alkaline earth metal equivalent; and optionally converting a compound of the general formula (I) obtained by processes (a), (b), (c) or (d) into a salt thereof.

5. A herbicidal composition, comprising at least one compound of the general formula (I) or a salt thereof as defined in any one of claims 1 to 3, and an extender, a surface-active agent or a mixture thereof.

6. Use of a compound of the general formula (I) or a salt thereof as defined in any one of claims 1 to 3, or a composition as defined in claim 5, for controlling undesired plant growth.

7. A method for controlling weeds, wherein a compound of the general formula (I) or a salt thereof as defined in any one of claims 1 to 3, or a composition as defined in claim 5, is allowed to act on the weeds or their habitat.

8. A method of preparing a herbicidal composition, wherein a compound of the general formula (I) or a salt thereof as defined in any one of claims 1 to 3 is mixed with an extender, a surface-active agent or a mixture thereof.

9. A compound of the general formula (IV):
wherein:

R1 is as defined in claim 1, excluding amino, C3-C8-alkylideneamino, di-(C1-C4-alkyl)-amino and (vi) as defined for R1 in claim 1;
R2 is as defined in claim 1, excluding amino, di-(C1-C4-alkyl) -amino and (vi) as defined for R1 in claim 1;
or R1 and R2 together are as defined in claim 1; and Z is as defined in claim 4.