CA2220494A1 - Sulphonylamino(thio)carbonyltriazolin(thi)ones with aryloxy or arylthio substituents - Google Patents

Abstract

The invention concerns sulphonylamino(thio)carbonyltriaxolin(thi)ones of formula (I) in which Q1 is oxygen or sulphur, Q2 is oxygen or sulphur, Q3 is oxygen or sulphur, R1 is hydrogen, hydroxy, amino, alkylidenamino or an optionally substituted group from the series alkyl, alkenyl, alkinyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R2 is substituted aryl when Q3 is oxygen and R2 is optionally substituted aryl when Q3 is sulphur, and R3 is an optionally substituted group from the series alkyl, arylalkyl, aryl and heteroaryl, plus salts of such compounds. The invention also concerns methods of preparing compounds of formula (I), intermediates for use in their preparation and the use of the compounds as herbicides.

Description

Le A 31 086-Forei~n countries / Bi/Ke/SW
.

Sulfonylamino(thio)ca~bonyll~iazolin(ethi)ones having aryloxy or arylthio substituen~

The invention relates to novel sulfonylamino(thio)carbonyltriazolin(ethi)ones having aryloxy or arylthio substituents, to a plurality of processes for their plepal~tion and to their use as herbicides.

5 Certain sulfonylaminocarbonyltriazolinones are already known to have herbicidal p~ ellies (cf. EP-A 341489, EP-A 422469, EP-A 425948, EP-A 431291, EP-A
507171). However, the activity of these compounds is not satisfactory in all aspects.

This invention, accordingly, provides the novel sulfonylamino(thio)carbonyltriazolin(ethi)ones having aryloxy or arylthio substituents 10 of the general formula (I) S~2--NH N, ~N--R
Q3 R2 (I~

in which Q' represents oxygen or sulfur, Q2 represents oxygen or sulfur, Q3 represents oxygen or sulfur, 15 R' represents hydrogen, hydroxyl, amino, alkyli~ien~mino or represents a respectively optionally substituted radical from the group con~i~ting of alkyl, alkenyl, alkinyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, Le A 31 086-Forei~n countries R2 represents substituted aryl when Q3 represents oxygen and represents optionally substituted aryl when Q3 represents sulfur and R3 represents a respectively optionally substituted radical from the group con~ ting of alkyl, aralkyl, aryl and heteroaryl, S and salts of compounds of the forrnula (I).

The novel sulfonylamino(thio)carbonyltriazolin(ethi)ones having aryloxy or arylthio substituents of the general formula (I) are obtained when (a) triazolin(ethi)ones of the general formula (II) ,1~
H--N N--R

=( 3 2 Q-R

in which Q', Q3, R' and R2 are each as defined above, are reacted with sulfonyl iso(thio)cyanates of the general formula (III) R3-So2-N=C=QZ (III) in which Q2 and R3 are each as defined above, if approl)liate in the presence of a reaction auxiliary and if apl)lop~iate in the presence of a diluent, Le A 31 086-Foreign countries or (b) triazolin(ethi)one derivatives of the general formula (IV) Z~--N N~
N =~
Q3 R2 (~
in which Ql, Q2, Q3, Rl and R2 are each as defined above and S Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted with sulfonamides of the general formula (V) R3So2-NH2 (V) in which R3 is as defined above, if appropl;ate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or Le A 31 086-Forei~n countries (c) triazolin(ethi)ones of the general forrnula (II) Q' H J~ ~R
N N
~3 R2 (Ll) in which Q~, Q3, Rl and R2 are each as defined above are reacted with sulfonarnide derivatives of the general formula (VI) R3-So2-NH-CQ'-Z (VI) in which Q2 and R3 are each as defined above and Z represents halogen, alkoxy, aralkoxy or aryloxy, if ~pr~liate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or - Le A 3 l 086-Forei~n countries (d) triazolin(ethi)ones of the general formula (II) ~l~NJ~N~
=(' 3 2 Q-R ~II) in which Ql, Q3, Rl and R2 are each as defined above are reacted with sulfonyl halides of the general formula (VII) R3-So2-X (VII) in which R3 is as defined above and X represents halogen, and metal (thio)cyanates of the general formula (VIII) l 0 MQ2CN (VIII) in which Q2 is as defined above and M represents an alkali metal or an alkaline earth metal equivalent, - Le A 31 086-Forei~n countries if appropl;ate in the presence of a reaction auxiliary and if a~plopliate in thepresence of a diluent, and the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are, if required, converted into salts by customary methods.

The novel sulfonylamino(thio)carbonyltriazolin(ethi)ones having aryloxy or arylthio substituents of the general forrnula (I) have strong herbicidal activities.

The invention preferably provides compounds of the formula (I) in which Q' represents oxygen or sulfur, Q2 represents oxygen or sulfur, 10 Q3 represents oxygen or sulfur, Rl represents hydrogen, hydroxyl, amino, Cl-C6-alkyliclen~mino, optionally fluorine-, chlorine-, bromine-, cyano-, C,-C4-alkoxy-, Cl-C4-alkyl-carbonyl- or Cl-C4-alkoxy-carbonyl-substituted Cl-C6-alkyl, represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C2-C6-alkenyl or C2-C6-alkinyl, represents respectively optionally fluorine- and/or chlorine-substituted Cl-C6-alkoxy, Cl-C6-alkylarnino, di-(Cl-C4-alkyl)-amino or Cl-C4-alkanoylamino, represents respectively optionally fluorine-, chlorine-, bromine- and/or Cl-C4-alkyl-substituted C3-C6-cycloalkyl or C3-C6-cycloalkyl-Cl-C4-alkyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, Cl-C4-alkyl-, trifluoromethyl-, Cl-C4-alkoxy- and/or Cl-C4-alkoxycarbonyl-substituted phenyl or phenyl-Cl-C4-alkyl, R2, in the case where Q3 represents oxygen, represents phenyl or naphthyl, each of which is substituted by cyano, carboxy, halogen, by Cl-C4-alkyl (which is optionally substituted by cyano, halogen or Cl-C4-alkoxy), by Cl-C4-alkoxy, - Le A 31 086-Forei~n countries .

C,-C4-alkyl-carbonyl, C,-C4-alkoxy-carbonyl or C,-C4-alkylthio (each of which is optionally substituted by cyano or halogen), by C3-C6-cycloalkyl, phenyl or phenyl-C,-C4-alkyl (each of which is optionally substituted by cyano, halogen, C,-C4-alkyl, C,-C4-halogenoalkyl, C,-C4-alkoxy and/or C,-C4-halogenoalkoxy), and, in the case where Q3 represents sulfur, represents phenyl or naphthyl, eachof which is optionally substituted by cyano, carboxy, halogen, by C,-C4-alkyl (which is optionally substituted by cyano, halogen or C,-C4-alkoxy), by C,-C4-alkoxy, C,-C4-alkyl-carbonyl, C,-C4-alkoxy-carbonyl or C,-C4-alkylthio (each of which is optionally substituted by cyano or halogen), by C3-C6-cycloalkyl, phenyl or phenyl-C~-C4-alkyl (each of which is optionally substituted by cyano, halogen, C~-C4-alkyl, C,-C4-halogenoalkyl, C,-C4-alkoxy and/or C~-C4-halogenoalkoxy), R3 represents the grouping ~R5 in which R4 and R5 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C,-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, Cl-C4-alkoxy-carbonyl, C,-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-alkylthio, C,-C4-alkylsulfinyl, C,-C4-alkylsulfonyl, di-(C,-C4-alkyl)-arninosulfonyl, C3-C6-cycloalkyl or phenyl), represents C2-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C,-C4-alkoxy-carbonyl, carboxy or phenyl), represents C2-C6-alkinyl (which is optionally substituted Le A 31 086-Forei~n countries .

by fluorine, chlorine? bromine, cyano, Cl-C4-alkoxy-carbonyl, carboxy or phenyl), represents Cl-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, Cl-C4-alkoxy-carbonyl, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-alkylsulfinyl or Cl-C4-alkylsulfonyl), represents Cl-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, Cl-C4-alkoxy-carbonyl, Cl-C4-alkylthio, Cl-C4-alkylsulfinyl or Cl-C4-alkylsulfonyl), represents C2-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or Cl-C4-alkoxy-carbonyl), represents C2-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Cl-C3-alkylthio or Cl-C4-alkoxycarbonyl), C3-C6-alkinyloxy, C3-C6-alkinylthio or represents the radical -S(O)p-R6 where, p represents the numbers 1 or 2 and R6 represents Cl-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or Cl-C4-alkoxy-carbonyl), C3-C6-alkenyl, C3-C6-alkinyl, Cl-C4-alkoxy, Cl-C4-alkoxy-C,-C4-alkylamino, Cl-C4-alkylamino, di-(C,-C4-alkyl)-amino, phenyl or represents the radical -NHoR7 where R7 represents Cl-Cl2-alkyl (which is optionally substituted by fluorine, chlorine, cyano, Cl-C4-alkoxy, Cl-C4-alkylthio, Cl-C4-alkylsulfinyl, Cl-C4-alkylsulfonyl, Cl-C4-alkyl-carbonyl, Cl-C4-alkoxy-carbonyl, Cl-C4-alkylamino-carbonyl or di-(CI-C4-alkyl)-amino-carbonyl), represents C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alkinyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-CI-C2-alkyl, phenyl-CI-C2-alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, Cl-C4-alkyl, Cl-C4-alkoxy or Cl-C4-alkoxy-carbonyl), represents benzhydryl or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, Cl-C4-alkyl, Le A 31 086-Forei~n countries trifluoromethyl, C~-C4-alkoxy, C~-C2-fluoroalkoxy, C~-C4-alkylthio, trifluoromethylthio or C,-C4-alkoxy-carbonyl), R4 and/or R5 furthermore represent phenyl or phenoxy, represent C~-C4-alkyl-carbonylamino, C,-C4-alkoxy-carbonylamino, C,-C4-alkylamino-carbonyl-amino, di-(C,-C4-alkyl)-amino-carbonylamino, or represent the radical -Co-R5 where R3 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-alkylamino or di-(C,-C4-alkyl)-amino (each of which are optionally substituted by fluorine and/or chlorine), R4 and/or R5 furthermore represent trimethylsilyl, thiazolinyl, C,-C4-alkyl-sulfonyloxy, di-(C,-C4-alkyl)-aminosulfonylamino or represent the radical -CH=N-R9 where R9 represents optionally fluorine-, chlorine-, cyano-, carboxy-, C,-C4-alkoxy-, C,-C4-alkylthio-, C,-C4-alkylsulfinyl-, or C,-C4-alkylsulfonyl-substituted C,-C6-alkyl, represents optionally fluorine- or chlorine- substituted benzyl, represents optionally fluorine- or chlorine-substituted C3-C6-alkenyl or C3-C6-alkinyl, represents optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, C,-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, represents optionally fluorine- and/or chlorine-substituted C,-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or benzyloxy, represents amino, C,-C4-alkylamino, di-(C,-C4-alkyl)-amino, phenylamino, C,-C4-alkyl-carbonyl-amino, C,-C4-alkoxy-carbonylamino, C,-C4-alkyl-sulfonylamino or represents optionally fluorine-, chlorine-, bromine- or methyl-substituted Le A 31 086-Forei~n countries phenylsulfonylamino, furthermore R'~ 12 R3 represents the radical I H~R

. R"

in which R'~ represents hydrogen or C,-C4-alkyl, R~ and Rl2 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C,-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), Cl-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxy, C,-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C~-C4-alkylsulfonyl or di-(C~-C4-alkyl)-aminosulfonyl;

furthermore R3 represents the radical R'3~3R14 in which lS R'3 and R'4 are identical or different and each represent hydrogen, fluorine, Le A 31 OX6-Forei~n countries .

chlorine, bromine, nitro, cyano, 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 S R3 represents the radical [~

in which R'5 and Rl6 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Cl-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C,-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), represents Cl-C4-alkylthio, Cl-C4-alkylsulfinyl or Cl-C4-alkylsulfonyl (each of which is optionally substituted by fluorine and/or chlorine), represent aminosulfonyl, mono-(C ,-C4-alkyl)-aminosulfonyl, represent di-(C,-C4-alkyl)-aminosulfonyl or C,-C4-alkoxy-carbonyl or dimethylaminocarbonyl;

1 5 furthermore R3 represents the radical R'7~3R'~

in which Le A 31 086-Foreign countries R~7 and Rl3 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, C,-C4-alkyl (which is optionally substituted by fluorine and/or bromine), C,-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), represents C,-C4-alkylthio, C~-C4-alkylsulfinyl or C~-C4-alkylsulfonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C,-C4-alkyl)-aminosulfonyl;

furthermore R
R3 represents the radical {~R2o in which R'9 and R20 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), Cl-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), Cl-C4-alkylthio, Cl-C4-alkylsulfinyl or C~-C4-alkylsulfonyl (each of which are optionally substituted by fluorine and/or chlorine), di-(CI-C4-alkyl)-amino-sulfonyl, Cl-C4-alkoxy-carbonyl or dimethylaminocarbonyl, and A represents oxygen, sulfur or the grouping N-ZI where Z~ replesents hydrogen, C~-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), Cl-C4-alkyl-carbonyl, Cl-C4-alkoxy-carbonyl or di(CI-C4-alkyl)-aminocarbonyl;

Le A 31 086-Forei~n countries furtherrnore R2l R3 represents the radical {~L~R22 y1 in which R2~ and R22 are identical or different and each represent hydrogen, C,-C4-S alkyl, halogen, C,-C4-alkoxy-carbonyl, C~-C4-alkoxy or C,-C4-halogenoalkoxy, Y' represents sulfur or the grouping N-R23 where R23 represents hydrogen or C,-C4-alkyl;

fiurthermore 10 R3 represents the radical ~R25 in which R24 represents hydrogen, C,-C4-alkyl, benzyl, pyridyl, quinolinyl or phenyl, R25 represents hydrogen, halogen, cyano, nitro, C,-C4-alkyl (which is Le A 31 086-Forei~n countries .
~ - 14 -optionally substituted by fluorine and/or chlorine), C,-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.

Furtherrnore, the invention preferably provides sodium, potassium, magnesiurn, calcium, ammoniurn, C,-C4-alkyl-ammonium, di-(C,-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-ammonium, tetra-(C,-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-sulfonium, C5- or C6-cycloalkyl-ammoniurn and di-(C,-C2-alkyl)-benzyl-ammonium salts of the compoundsof the formula (I) in which Ql, Q2, Q3, R', R2 and R3 each have the preferred meanings given above.

The invention in particular provides compounds of the forrnula (I) in which Ql represents oxygen or sulfur, Q2 represents oxygen or sulfur, Q3 represents oxygen or sulfur, 15 R' represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylarnino, n- or i-propylamino, n-, i-, s- or t-butylarnino, dimethylamino or diethylarnino, represents respectively optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-, trifluoromethyl- or methoxy-substituted benzyl or phenyl, Le A 31 086-Forei~n countries R2, in the case where Q3 r~rese~ oxygen, represents cyano-, carboxy-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butyloxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, methylthio-, ethylthio-, cyclopentyl-, cyclohexyl-, phenyl- or benzyl-substituted phenyl, and, in the case where Q3 represents sulfur, represents optionally cyano-, carboxy-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butyloxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, acetyl-, proponyl-,methoxycarbonyl-, ethoxycarbonyl-, methylthio-, - ethylthio-, cyclopentyl-, cyclohexyl-, phenyl- or benzyl-substituted phenyl, ~R5 R3 represents the radical ~
~,~4 in which R4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n or i-butoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy, 1,1,2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, methylthio, ethylthio, n- or i-propylthio, n- or i-butylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N-methylaminosulfonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and R5 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or Le A 31 086-Foreign countries trifluoromethyl;

furthermore R3 represents the radical CH ~5 in which Rl~ represents hydrogen, Rll represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl and Rl2 represents hydrogen;

1 0 furthermore R3 represents the radical Ro~

in which Le A 31 086-Forei~n countries R replcsell~s methyl, ethyl, n- or i-propyl, or R3 represents the radical J~ I

in which R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, R25 represents hydrogen, fluorine, chlorine or bromine, R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.

The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the precursors or intermediates required in each case for the plepaldtion. These radical definitions can be combined 10 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 straight-chain or branched, even in combination with hetero atoms, as in alkoxy, alkylthio or alkylamino, even if this is not explicitly stated.

15 Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Using, for example, 2-trifluoromethoxy-phenylsulfonyl isocyanate and 4-ethyl-5-(2-fluoro-phenoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of Le A 31 086-Forei~n countries the reaction in the process (a) according to the invention can be illustrated by the following scheme:

o ,~ O-CF3 [~ ' ~ H_N)~N--C2Hs ~SO c NJ~N c2Hs ~F~l C~

Using, for example, 2-ethylthio-benzenesulfonamide and 2-chlorothio-carbonyl-4-cyclopropyl-5-(4-cyano-phenoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one as starting5 materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following scheme:

~50 Cl ~ [~SO, NH N~ ~

~CN (~CN

Using, for example, N-methoxycarbonyl-2-methoxy-benezenesulfonamide and 4-methyl-5-phenylthio-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (c) according to the invention can be illustrated by the following 10 scheme:

[~ N=~ 3 NH =
SO2-NH-COOCH3 C6Hs S--CsH5 Le A 31 086-Forei~n countries Using, for example, 2-chloro-6-methyl-ben7~n~sulfonyl chloride, 4-allyl-5-(4-chloro-phenylthio)-2,4,-dihydro-3H-1,2,4-triazol-3-one and sodium cyanate as starting materials, the course of the reaction in the process (d) according to the invention can be illustrated by the following scheme:

~ H_NJ~N--CH2-cH=cH2 ~0 J~--NJ~N--CH2-CH=CH2 Cl ~3~C NaCI S~C

5 A general definition of the tri~olin(ethi)ones to be used as starting materials in the processes (a), (c) and (d) according to the invention for plt;pa~ g compounds of the formula (I) is given by the formula (II).

In the formula (II), Q', Q3, R' and R2 each preferably or in particular have those meanings which have already been indicated above, in connection with the description 10 of the compounds of the formula (I) according to the invention, as preferred or particularly preferred for Q', Q3, R' and R2.

The triazolin(ethi)ones of the general formula (II) are known and/or can be prepared by processes known per se (cf. EP 507171, DE 3924571, US 4098896, J. Org. Chem. 50 (1985), 1295-1298).

lS The triazolin(ethi)ones of the formula (II) are obtained when (thio)carbazates of the general formula (IX) 1~
NH O
NH2 R2 (L~

in which ~ CA 02220494 1997-11-07 Le A 31 086-Forei~n countries Q' is as defined above and R27 represents alkyl (preferably methyl or ethyl) are reacted with imino(di/thio)carbonic diesters of the general formula (X) ~ a3 ~Q3 / (X) S in which Q3, Rl and R2 are each as defined above, if appropriate in the presence of a diluent such as, for example, N,N-dimethyl-forrnamide, and if a~lopliate in the presence of a reaction auxiliary such as, for - example, hydrochloric acid or pivalic acid, at temperatures between 0~C and 100~C, 10 and the resulting compounds of the general formula (XI) N O
N~NH
Q ~
R (X~) in which Q', Q3, R', R2 and R~7 are each as defined above are cyclocondensed - if a~ropliate after interrnediate isolation - if appropriate in the Le A 31 086-Forei~n countries presence of a diluent such as, for example, toluene, and if a~ o~liate in the presence of a reaction auxiliary such as, for example, sodium hydroxide or sodium methoxide, at temperatures between 20~C and 150~C (cf. the Plel)ald~ion Examples).

The triazolin(ethi)ones of the general formula (II) can also be obtained by reacting 5 triazolin(ethi)ones of the general formula (IIa) Q3 R2 ~a) in which Ql, Q3 and R2 are each as defined above with alkylating agents of the general formula (XII) X'-R' (XII) 10 in which R' is as defined above and X' represents halogen or the grouping -O-SO2-R', if applopliate in the presence of an acid acceptor such as, for example, potassium carbonate, and if a~propliate in the presence of a diluent such as, for example,15 acetonitrile, at tempelalules between 0~C and 100~C (cf. the preparation examples).

Furthermore, the triazolin(ethi)ones of the general formula (II) can also be obtained by reacting triazolin(ethi)ones of the general formula (IIb) Le A 31 086-Forei~n countries H--N ~N_R
~ 3(~) M

in which Q~, Q3 and Rl are each as defined above - however Q3 preferably represents sulfur -and M represents a metal equivalent, preferably sodium or potassium, 5 with diazonium salts of the general formula (XIII) N2-R2~ XO (~I) in which R2 and X are each as defined above, in the presence of a catalyst such as, for example, copper(II) chloride and in the presence of water and, if appropriate, an organic diluent such as, for example, 10 methylene chloride, at tempeld~ul~s between 0~C and 50~C (cf. the Ple~ ion Examples).

A general definition of the sulfonyl iso(thio)cyanates further to be used as starting materials in the process (a) according to the invention for p~e~ g compounds of the formula (I) is given by the formula (III).

15 In the formula (III), Q2 and R3 each preferably or in particular have those me~ning~
which have already been indicated above, in connection with the description of the -Le A 31 086-Forei~n countries compounds of the formula (I) according to the invention, as preferred or particularly - preferred for Q2 and R3.

The starting materials of the formula (III) are known and/or can be prepared by processes 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 triazolin(ethi)one derivatives to be used as starting materials in the process (b) according to the invention for prepaling compounds of the general formula (I) is given by the formula (IV). In the formula (IV), Q~, Q2, Q3, R~ and R2 each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as preferred or as particularly preferred for Q', Q2, Q3, R' and R2; here, Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogeno-or nitro-phenoxy, in particular methoxy, phenoxy or 4-nitro-phenoxy.

The starting materials of the formula (IV) have not been disclosed in the literature; as novel compounds, they also form part of the subject matter of the present application.

The novel compounds of the formula (IV) are obtained when triazolin(ethi)ones of the general formula (II) Q' N N
N =( Q3 R2 (II) 20 in which Q', Q3, R' and R2 are each as defined above Le A 31 086-Forei~n countries -are reacted with carbonic acid derivatives of the general formula (XIV) Z CQ2ZI ~V) in which Q2 and Z are each as defined above and S Z' represents halogen (in particular chlorine), alkoxy (in particular methoxy), aralkoxy (in particular benzyloxy) or aryloxy (in particular phenoxy), if applol,liate in the presence of an acid acceptor such as, for example, sodium hydride or potassium hydride, sodium hydroxide or potassiurn hydroxide, sodium t-butoxide or potassium t-butoxide, and if appropliate in the presence of a diluent such as, for example, tetrahydrofuran or dimethoxyethane, or in a two-phase system of water and an organic solvent such as, for example, methylene chloride or chloroform at temperatures between 0~C and 100~C.

A general definition of the sulphonamides further to be used as starting materials in the process (b) according to the invention for ple~ g compounds of the general formula (I) is given by the formula (V). In the formula (V), R3 preferably or in particular has those meanings which have 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 plepa~ g compounds of the formula (I) Le A 31 086-Forei~n countries .

is given by the formula (VI). In the formula (VI), Q2 and R3 each preferably or in particular have those me~ning~ which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable orparticularly preferable for Q2 and R3; here, Z preferably represents fluorine, chlorine, 5 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 10 process (d) according to the invention for plep~illg compounds of the formula (I) is given by the formula (VII). In the formula (VII), R3 preferably or in particular has those meanings which have 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 in15 particular represents chlorine.

The starting materials of the formula (VII) are known and/or can be prepared by methods known per se. This also applies to the starting materials and intermediates of the formulae (VIII) to (XIV).

The processes (a), (b), (c) and (d) according to the invention for the plepa alion of the 20 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 25 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 Le A 31 086-Forei~n countries propionitrile; arnides, for example dimethylformamide, dimethyl~cet~mide and N-methylpyrrolidone, and also dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphoric triamide.

As reaction auxiliaries and/or as acid acceptors in the processes (a), (b), (c) and (d) 5 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 tert-butoxide and potassium tert-10 butoxide, and also basic nitrogen compounds, such as trimethylamine, triethylamine,tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, 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-di~z~bicyclo-[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 +100~C, preferably at temperatures 20 between 0~C and +80~C.

The processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric ples~ule. 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 25 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 carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a Le A 31 086-Forei~n countries 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 methods (cf. the Preparation Examples).

Salts of the compounds of the general formula (I) according to the invention can be 5 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 app,opliate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an al~plopliate base. The salts can then - if desired after prolonged stirring - be isolated by concentration or filtration with suction.

10 The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed-killers. By weeds, in the broadest sense, 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.

15 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, 20 Solanum, Rorippa, Rotala, T in~1erni~, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus,Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

25 Monocotyledonous weeds of the ~enera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Le A 31 086-Forei~n countries Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocot,vledonous crops of the ~enera: Oryza, Zea, Triticum, Hordeum, Avena, 5 Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no wayrestricted 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 weeds, for example on industrial terrain and rail tracks, and on paths and squares with 10 or without tree pl~ntin~ Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit pl~nting~ and hopfields, in lawns, turf and pasture-land, and for the selective control of 15 weeds in annual crops.

The compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both pre-emergence and post-emergence.

To a certain extent, the compounds of the formula (I) also have fungicidal activity, for 20 example against Pyricularia oryzae in rice.

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.

25 These formulations are produced in a known manner, for example by mixing the active Le A 31 OB6-Forei~n counkies compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surf~ct~ntc, 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 5 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 pekoleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers 10 and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, skongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, as well as water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, 15 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 20 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, alkylsulfonates, alkyl sulfates, arylsulfonates as well as protein hydrolysates; suitable dispersing agents are: for example lignin-sulfite waste liquors and methylcellulose.

25 Tackifiers 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 Le A 3 l 086-Forei~n countries 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, m~ng~nese, boron, S copper, cobalt, molybdenum and zinc.

The formulations in general comprise between 0. l and 9S per cent by weight of active compound, preferably between O.S 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, lO ready-to-use formulations or tank mixes being possible.

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 15 diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-me~.hyl and qui_alofop-ethyl; a_inones, such as chloridazon and norflurazon; carbamates, such as chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, such asalachlor, acetochlor, butachlor, met~7~cll10r, metolachlor, pretilachlor and propachlor;
dinitro~nilin~s, such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, such as 20 acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen;
ureas, such as chlorotoluron, diuron, fluometuron, isoproturon, linuron and methaben7thi~711ron; hydroxyl~min~s, such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as ima_ethapyr, im~7~methabenz,im~7~pyr and ima_aquin; nitriles, such as bromoxynil, dichlobenil and ioxynil;
25 oxyacetamides, such as mefenacet; sulfonyl-ureas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarb~m~tes, such as butylate, cycloate, ~ te, EPTC, Le A 31 0~6-Forei~n countries esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazine, ~im~7ine, simetryne, terbutryne and terbutylazine; triazinones, such as hexazinone, metamitron and metribuzin; others, such as aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, defenzoquat, dithiopyr, ethofumesate, S fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.

10 The active compounds can be used as such, in the form of théir 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 manner, for example by watering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied either before or after 15 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 S g and 2 kg per ha.

20 The p~ lion and use of the active compounds according to the invention can be seen from the examples below.

Le A 31 086-Forei~n countries Plcp~dlion examples:

Example 1 2 - NH ~OCH
0~

(Process (b)) 1.8 g (5 mmol) of 2-phenoxythiocarbonyl-4-methyl-5-(2-methoxy-phenoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one are added to a mixture of 1.1 g (5 mmol) of 2-trifluoromethyl-benzenesulfonamide, 0.8 g (5 mmol) of 1,8-diazabicyclo-5.4.0]-undec-7-ene (DBU) and 50 ml of acetonitrile, and the reaction mixture is stirred at about 20~C for about 15 hours. The mixture is then concentrated using water pump vacuum and the residue is taken up in methylene chloride, washed with lN hydrochloric acid, dried with sodium sulfate and filtered. The filtrate is concentrated using water pump vacuum, the residue is digested with diethyl ether and the resulting crystalline product is isolated by filtration with suction.

1.3 g (53 % of theory) of 2-(2-trifluoromethyl-phenylsulfonyl-aminothiocarbonyl)-4-methyl-5-(2-methoxy-phenoxy)-2,4-dihydro-3H- 1 ,2,4-triazol-3-one of melting point 143~C are obtained.

Le A 31 086-Foreign countries Example 2 S~~ - NH N N
N =~ OCH3 o~3 (Process (d)) A mixture of 2.2 g (10 mmol) of 4-methyl-5-(2-methoxy-phenoxy)-2,4,-dihydro-3H-1,2,4-triazol-3-one, 2.6 g (10 mmol) of 2-trifluoromethoxy-benzenesulfochloride, 1.3 g 5 (20 mmol) of sodium cyanate and S0 ml of acetonitrile is heated at reflux for 15 hours.
The mixture is then concentrated using water pump vacuum and the residue is taken up in methylene chloride, washed with lN hydrochloric acid, dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate using water pump vacuum.

2.7 g (56 % of theory) of 2-(2-trifluoromethoxy-phenylsulfonyl-aminocarbonyl)-4-methyl-5-(2-methoxy-phenoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained as a crystalline residue of melting point 154~C.

By the methods of Examples 1 and 2 and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, for 15 example, the compounds of the formula (I) listed in Table 1 below.

Q2 Q' S~2 - NH , N

N=( Q3 R2 (I) Le A 31 086-Forei~n countries Table 1: Examples of compounds of the formula (I) Ex. Ql Q2 Q3 Rl R2 R3 Melting No point (~C) 3 O O O CH3 ~cl ~cooc~, 175 4 O O O CH3 ~CI ~cOOcH, 130 O O O CH3 ~ [~cooa1, 164 6 O o O CH3 ~cl ~OCHF2 147 7 0 0 0 CH3 "Q ~OCHf2 143 8 O O O CH3 ~cl [~OCHF2 172 9 O O O CH3 ~CI ~CH3 130 0 o O CH3 ~ [~CH3 150 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 11 0 0 0 CH3 ~cl [~CH3 140 12 O O O CH3 ~cl ~CF3 205 3 ~ ~ ~ CH3 ~ CF3 210 14 O o o CH3 ~cl [~CF3 210 O O O CH3 COOCH3 ~OCHF2 150 16 O ~ ~ CH3 COOCH3 ~CH3 158 17 O ~ ~ CH3 COOCH3 [~CF3 185 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 18 O O O CH3 ~ [~OCHF2 142 \~SCH, ~

O O O CH3 ~ ~CF3 180 21 O o o CH3 ~OCH3 ~COOCH, 140 22 O ~ ~ C2H5 COOCH3 ~Br 132 23 O ~ ~ C2H5 ~g3OCH3 ~CF3 130 24 O ~ ~ C2H5 COOCH3 coOCH3 134 O O O C2H5 ~cl ~Br 145 Le A 31 086-Forei~n countries Table 1: (Continued) Ex Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 26 O O O C2H5 ~,cl ~Br 100 27 O o o CH3 ~c~ ~COOCH, 128 28 O O O CH3 ~ ~ ~COOCH~ 154 29 O o o CH3 ~cc~, I~COOCH, 153 O O O CH3 '13~ ~cOOCH, 120 31 O ~ ~ CH3 ~a1, ~CF3 145 O O O CH3 ~OC2H~ ~CF3 125 33 O O O CH3 '13~ 0~CF3 I go 34 O O O CH3 ~cl ~F 185 Le A 31 086-Forei~n countries - 38 -Table 1: (Continued) Ex. Q 1 Q2 Q3 R I R2 R3 Melting No. point (~C) 3 5 0 0 0 CH3 ~1 ~COOCH, 150 36 O O O CH3 ~3 ~CF, ~06 37 O O O CH3 cl CH3 142 38 o O O CH3~[~lOCH3 C~ Cl 160 39 O O O C2H5cl ~cOOc,H, 145 O o O C2H5'13~ ~cooc~ 117 41 0 0 0 CH3 ~ CF3 180 42 o O O C2Hs~CI ~CooC,H, 133 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q I Q2 Q3 R I R2 R3 Melting No. point (oC~
43 O O O C2H5 ~3~ ~coocy, 145 44 O O O C2Hs ~CI ~cOOc,H, 142 O O O C2Hs ~,cl ~CF3 130 46 0 0 0 ~0~ CF3 136 ~ O C2E~5 ~ ~CF~ 162 48 0 ~ ~ CH3 COOCH,SC2H5 125 49 o O O CH3 c~SC2H~ 152 \~ ~

O o O CH3 ~ [~SC7Hs 128 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 51 O ~ ~ CH3 cl ~cooc~, 199 52 0 0 0 C83 ~[~ ~CF3 182 53 O O O CH3 cl ~ F 192 '1~1 ~

54 0 0 0 C2H5 Cl @~COOclH, 130 55 0 0 0 C~85 ~[~ r 150 Le A 31 086-Forei~n countries Table 1: (Continued) No. Q2 Q3 Rl R2 R3 M It 56 0 0 0 ~ ~ ~CH3 200 CH3 Cl 5~ ~ ~ ~ ~'~ ~ 0~cH, 165 S8 O O o f~ Cl [~cooc2H~ 168 59 0 0 0 ~ ~ ~CF3 170 0 0 0 ~ Cl ~COOCH, 180 CH, Le A 31 086-Forei~n countries Table 1: (Continuecl) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 61 0 0 0 ~ ~ [~CH3 14~

6~ 0 0 0 ~ ~[~3 [~C~SI~ 137 63 0 0 0 ~ ~ CF3 190 64 0 0 0 ~ CH3 177 65 0 0 0 ~ Cl ~CO~ 172 66 0 0 0 ~ F~CF3 120 67 0 0 0 ~ OCH3 ~COOCH, 150 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 68 O ~ ~ CH3 OCH3 ~COOCH, 1 78 69 O ~ ~ CH3 ~C2H5 ~COOCH~ 147 \~ , O O O CH3 ~[~Hs ~CF~ 175 71 0 0 0 CH3~H3 0~CF3 196 72 O O O CHOCH3 [~CH3 180 73 O O O CH3~Hs ~CH3 152 74 ~ O O C2H5 OCH3 146 ~C~H, Le A 31 086-Forei~n countries ~ - 44 -Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) O O O C2H5 ~[~H3 ~C~3 12 O O O C2H5 ~3H3 ~Br 126 ~ ~ ~ C2HS ~H5 - ~Br 125 O O C2Hs ~3H3 ~COOCH, 79 0 0 0 ~,~ ~lH3 ~COOC,H, 135 ~, 0 0 0 ~ ~H5 0~c~

Le A 31 086-Forei~n countries Table 1: (Continued) No. Q2 Q3 Rl R2 R3 Melting 81 o o o ~ ~5 ~coocH, 141 82 o o o C2Hs~[~Hs ~COOCH~ 1 s8 83 0 0 0 ~OCH3 ~CH3 102 84 0 0 0 ~~Hs @~CH, 106 8~ O o O ~ ~

86 0 0 0 ~ ~H5 [~CH3 146 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No point (~C) 87 O ~ ~ CH3 OCH3 ~SC2Hs 1 34 O O CH3 ~[~H5 ~SC,H, 89 o o o CH3 ~H~ ~F 150 O O O CH3 ~Hs ~F 145 ~ COOCH3 ~OCHF2 127 92 O O O ~ COOCH, 0~r 135 93 ~ ~ O ~ COOCH3 0~CF3 1 40 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) O O O ~,~ ~,~H3 ~OCHF2 o o o ~ ~ ~OC11F, 96 0 0 0 ~ ~Hs ~OCHF2 132 97 o O O C2H5 ~ ~ 162 98 O O O ~ Cl [~CH3 180 (Na salt) Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 99 ~ O O ~ ~ ~Br 155 100 0 0 0 ~ CF3 180 (Na salt) 101 O O O CH3 p ~ 3 198 ~3 102 O o O ~ ~ 0~CF3 140 103 o O O ~ ~ ~ ~Br 168 Le A 31 086-Forei~n countries Table 1: (Continll~cl) Ex. Q I Q2 Q3 R I R2 R3 Melting No point (~C) 104 O O O ~ ~ ~co~ 140 105 O O O CH3 ~ ~COOCH, 150 ~.

106 O O O CH3 p [~OCF3 155 ~3 107 O o o CH3 p ~cH3 133 ~3 Cl 108 O o o CH3 p [~SC2H5 164 ~1 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q I Q2 Q3 R I R2 R3 Melting No point (~C) 109 O o O CH3 p ~ 215 ~3 110 O O O C2H5 ~ ~ooc~ 157 ~3 ~1 112 O O O ~ ~cH, [~CF3 145 113 O O O ~ ~CH, [~OCHFz 50 Le A 31 086-Forei~n countries .

Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 114 O O O ~ ~ ' ~c~ 168 115 O O O CH3 OCH3 ~COOCH, 130 ~ (Na salt) 116 O O O CH3 ~Hs ~c~ 130 ~ (Na salt) 7 O O O CH3 ~Hs [~CF3 180 (Na salt) 118 O O O C H OCH3 [~coocH, 125 ~J (Na salt) 119 0 0 0 ~ OCH3 ~COOC,H, 173 (Na salt) Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q I Q2 Q3 R I R2 R3 Melting No. point (~C) 120 O O O ~,~ ~H5 ~cooc 135 1~ (Na salt) 121 O O O ~ ~Hs ~COOCH, ~ (Na salt) 122 O O O C2H5 ~H5 ~COOCH, l~ (Na salt) 123 O O O ~ \~CH, [~CF3 170 (Na salt) 124 O O O CH3 ~a 125 O O O C2H5 ~a [~

126 O o o CH3 ~CH~ [~F 203 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 127 O O O ~ ~ [~

128 O O O ~ F ~OCHF2 136 ~3 130 o O O ~ F [~CH3 145 131 O O O C2H5 ~ ~ 13 8 132 O O O ~ F ~CF3 142 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C~
133 0 0 0 ~ ~ ~OCHF, ~ O O CH3 ~ ~ 150 ~ F

136 0 0 0 ~ ~ [~CH3 124 137 0 0 0 ~ ~ ~ 90 ~F

Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q I Q2 Q3 R I R2 R3 Melting No point (~C) 139 0 0 0 ~ F ~CH3 116 ~ F ~ccoyl, 122 141 0 0 0 ~,~ ~3~ ~ 147 142 0 0 0 ~ F ~CF3 154 143 O O O ~ F ~COOCH, 168 144 O O O ~ ~ [~ 150 Le A 31 086-Forei~n countries Table 1: (Continl-e-l) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) ~er ~ ~ O CH3 ~ (~CF~ ~4 147 0 0 0 H ~3H, [~CF3 92 8 O O O CH3 ~H3 ~cooc,HT 120 O O O CH3 ~H3 ~CH3 174 O H3 @~cooc~ 122 Le A 31 086-Forei~n countries -Table 1: (Continued) Ex Q I Q2 Q3 R I R2 R3 Melting No. point (~C) I S 1 O S ~ CH3 ~W ~

152 o S ~ CH3 OCH3 ~OCHF2 142 W

153 o o S CH3 COOCH3. COOCH3 218 154 O o S CH3 COOCH3COOCH3 1 60 ~3 (Isopropyl-salt) 155 O O S f~ COOCH3~OCH3 114 156 O O S CH3 ~3 3 ~ 3 156 Le A 3 1 086-Forei~n countries Table 1: (Continued) Ex. Ql Q2 Q3 Rl R2 R3 Melting No. point (~C) 157 O O S CH3 COOCH3 [~CF3 200 158 O O S CH3 COOCH3 [~OCF3 198 159 O O S CH3 COOCH3 ~OCHF2 1 89 160 O O S CH3 COOCH3 [~3~ 3 180 161 O O S CH3 COOCH3 ~OCH3 1 80 162 O O S CH3 COOCH3 ~OC2H, 192 163 O O S CH3 COOCH3 ~SC2H5 204 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q I Q2 Q3 R I R2 R3 Melting No. point (~C) 164 O O S CH3 ~ ~'~~

165 O O CH ~ ~oc~, 179 166 O O O CH3 ~H~ ~ 190 O C~3 ~H~ ~OCHF, 168 O O S ~ ~ ~cooo~ 176 169 O O S ~ ~ ~~CHF2 141 170 O o S CH3 ~ ~cooo~ 154 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q 1 Q2 Q3 R I R2 R3 Melting No. point (~C) 171 o o S CH3 ~3 [~OCHF2 172 0 0 S CH3 ~3 ~OCF3 148 173 0 0 S CH3 ~ CH3 1 80 174 0 ~ S CH3 \~3 [~ 3 1 65 O O S CH3 ~3 ~OCH3 141 176 0 0 S CH3 \ 3 0~CH3 92 Le A 31 086-Forei~n countries Table 1: (Continued) Ex. Q I Q2 Q3 R I R2 R3 Melting No. point (~C) 177 0 O S CH3 ~0 ~OC2Hs 119 178 o o S CH3 ~3 ~sc2H5 136 179 0 O S CH3 ~3 ~ 124 180 O O S ~ COOCH3 [~CH3 133 OC3H,-n 181 0 0 0 CH3 ~3 OCH3 O O CH3 ~3H3 [~OCH, OC,H,~

Le A 31 086-Foreign countries Sta~ matenals of the folmula (II):

Example (II-1) H--N N_CH3 N~
0 ~

Cl ~-1) At 20~C, a solution of 105 g (0.69 mol) of phenyl - calba~e in 175 ml of dimethylformamide is added dropwise with stirring to a mixture of 205 g (0.69 mol) of 5 bis-(4-chloro-phenyl) methyliminocarbonate and 250 ml of dimethylformamide. The reaction mixture is stirred at 20~C for 16 hours and then, using water pump vacuum (about 15 mbar), slowly heated to about 100~C to distill off most of the dimethylformamide. The remainder of the volatile components is then removed at about 150~C using oil pump vacuum (about 1 mbar). At about 0.1 mbar/200~C, the residueaffords 25 g of a sublimate which yields, after digestion with isopropanol, 15 g (10 %
of theory) of 5-(4-chloro-phenoxy)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 196~C.

Example (II-2) H_NJ~N--CH3 N = ( l CH3 ~-[~
(II-2) 9.7 g (77 mrnol) of dimethyl sulfate are added dropwise with stirring to a mixture of 15.4 g(70 mmol) of 5-(2-methoxy-phenoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one,10.6 g Le A 31 086-Forei~n countries (77 mmol) of potassium carbonate and 100 ml of acetonitrile which has been heated to 50~C. The reaction ~ e is stirred at 50~C for 15 hours and then cooled to room temperature (about 20~C) and filtered off with suction. The filtrate is evaporated to dryness using water pump vacuum, and the residue is digested with diethyl ether. The 5 resulting crystalline product is isolated by filtration with suction.

13 g (84 % oftheory) of 5-(2-methoxy-phenoxy)-4-methyl-2,4-dihydro-3H- 1,2,4-tri~ol-3-one of melting point 105~C are obtained.

Example (II-3) H--N N_CH3 N=~

--[~coOCH3 (II-3) 30.2 g (0.20 mol) of methyl 4-amino-benzoate are suspended in 100 ml of water and treated with 50 g of 37 % strength hydrochloric acid (0.5 mol of HCI). At 0~C to-10~C, a solution of 14.1 g (0.20 mol) of sodium nitrite in 30 ml of water is added dropwise with vigorous stirring and cooling. At about 10~C, the resulting di~onium salt solution is added dropwise to a solution of 34 g (0.20 mol) of the potassium salt of 5-mercapto-4-methyl-2,4-dihydro-3H-1,2,4-tri~ol-3-one24.6 g (0.30 mol) of sodium acetate and 100 mg of copper(II) chloride in 250 ml of water, causing the reaction to foam with nitrogen being released. Subsequently, the reaction is admixed with 300 ml of methylene chloride and the mixture is stirred at 20~C for a further 12 hours. The white solid that has formed is isolated by filtration with suction and washed successively with water, isopropanol and diethyl ether. A second product fraction is 20 obtained by drying and conce~ hlg (water pump vacuum) the methylene chloride phase, stirring the residue with isopropanol and filtration with suction.

Total yields: 27.9 g (52.5 % of theory) of 5-(4-methoxycarbonyl-phenylthio)-4-methyl-Le A 31 086-Forei~n countries 2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 196~C.

By the methods of Examples (II-1) to (II-3), it is also possible to prepare, for example, the compounds of the formula (II) listed in Table 2 below.

Le A 31 086-Forei~n countries H_NJ~N_R' Q3 R2 (II) Table 2: Examples of compounds of the forrnula (II) Ex. - Ql Q3 Rl R2 Melting point No. (~C) II~ O S CH3 COOCH3 188 II-6 O S CH3 ~COOCH3 137 II-7 O S CH3 ~COOH 182 II-8 O S CH3 ~ 293 COOH

II-9 o S "~ COOCH3 175 ~3 ' Le A 31 086-Forei~n countries Table 2: (Continued) Ex. Ql Q3 R R2 Meltingpoint No. (~C) II- 1 1 O S ~ \~31 II-12 O S CH3 ~3 II-14 O O CH3 ~CI

II-l 5 O o CH3 ~3~CI

II-16 O O CH3 ~

II-17 O O CH3 ~CH3 Le A 31 086-Forei~n countries Table 2: (Continued) Ex. Ql Q3 R R2 Meltingpoint No. (~C) ~I- 19 0 ~ CH3 ~3 II-20 O O CH3 \~CH3 Cl II-2 1 O ~ CH3 F

\[~F

II-22 O ~ CH3 F

F

II-23 O O ~
~3 II-24 0 0 ~ ~CH3 Cl Le A 31 086-Forei~n countries -Startin~ materials of the formula (IV):

Example (IV-l) s ~
HsC6_ ~--N N-- 3 N =( OCH3 0~

(IV-I) A solution of 5.7 g (33 mmol) of phenyl chlorothioformate in 30 ml of methylene chloride is added dropwise with stirring to a mixture of 6.6 g (30 mmol) of 5-(2-methoxy-phenoxy)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one, 30 ml of water, 1.3 g (33 mmol) of sodium hydroxide and a spatula tip of triethylbutylammonium chloride (TEBA), and the reaction mixture is sitrred at 20~C for 15 hours. The organic phase is then separated off, dried with sodium sulfate and filtered. The filtrate is concentrated, the residue is digested with diethyl ether and the resulting crystalline product is isolated by filtration with suction.

7 g (65 % of theory) of 5-(2-methoxy-phenoxy)-4-methyl-2-phenoxythiocarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 138~C are obtained.

By the method of Example (IV-1), it is possible to prepare, for example, the compounds of the formula (IV) listed in Table 3 below.

Q2 Q' --N J~ N--R

Q3 R2 (~

Le A 31 086-Forei~n countries Table 3: Examples of compounds of the fo~nula (IV) Ex. Q Q2 Q3 Rl R2 z Melting point No. (~C) IV-2 O O ~ CH3 ~3OCH3 H C O

IV-3 O O O CH3 ~ HsC6O

IV 1 0 0 O CH3 ~ H5C6O

IV-5 O O O CH3 ~ HSC6O

IV-6 O O S CH3 ~3 H5C6O

IV-7 O O O ~ ~3~cl HsC6O

IV-8 o O S ~ ~3 H5C6O

IV-9 O O O ~ HsC6O
'~3 Le A 31 086-Forei~n countries Table 3: Examples of compounds of the formula (IV) Ex. Ql Q2 Q3 Rl R2 z Melting point No. (~C) IV- 10 O ~ ~ CH3 HsC6O

IV-I I O ~ ~ CH3 H3CO
~, ,.

Le A 31 086-Forei~n countries Application 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 l"ep~dlion of active compound, 1 part by weight of active compound is mixed with the stated amount of the solvent, the stated amount of emulsifiers is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered or sprayed with the active compound preparation. It is advantageous to keep the amount of water per unit area constant. The concentration of active compound in the prepaldlion is of no importance, only the amount of active compound per unit area being decisive.

After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control. The figures denote:

0 % = No effect (like untreated control) 100 % = Total destruction In this test, the compounds of P~e~alalion Examples 9, 15, 16, 17, 21, 23, 24, 66, 129, 131, 132, 135, 137 and 140, for example, exhibit strong activity against weeds.

Table A: Pre-emergence test/greenhouse r -Compound of Application Alo- Bromus PoaSetaria Cheno- Portu- Sina- Sola- ~
preparation rate(g/ha) pecurus podium laca pisexample No. rq 9 500 80 - 70 80 70 80 100 80 c 1 5 125 80 - 95 90 70 90 9S 9S ~ ~
16 125 9S 95 95 95 95 100 loo 95 17 125 95 95 95 95 80 9S loO 95 ~ ~

~.23 250 90 9S 95 9S 9S 9S 90 9S
24 . 250 95 95 95 95 9~ 95 90 9S

Table A: (Continued) x Compoundof Application Alo- Bromus PoaSetaria Cheno- Po~ Sina- Sola- ~
preparation rate (g/ha)pecun~s podium laca pis num exampleNo. ~, 132 125 - 95 95 95 95 9S 9S 9S ~D O

Le A 31 086-Forei~n countries .

Example B

Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether S To produce a suitable prepalation of active compound, 1 part by weight of active compound is mixed with the stated amount of the solvent, the stated amount of emulsifiers 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 active compound 10 ple~ ion 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 applied in 1000 l of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control.

15 The figures denote:

0 % = No effect (like untreated control) 100 % = Total destruction In this test, the compounds of Plel)a~lion Examples 4, 5, 13, 15, 16, 17, 21, 23, 24, 66, 128, 129, 131 and 137, for example, exhibit strong activity against weeds.

Le A 31 086-Forei~n countries o ~ ~ ~ ~ O~ O~ ~ O~ ~ O o p~ o 't' ~ o~ ~ O~ o 4 ~' ~' _ ~ o O o O

,= , , o -O~ ~ ~ ~ ~ v' O

~ o o O~ o O ~ ~ o o o O~ ~ ~ ~ ~ O~ o o o u~
o ~ Ov~ o o o ~ o o o o r o ._ ~

c .5 ~ o ~O ,,, ' ~0 ~o ~ o Z

E o ' x m Table B: fContinued) CompoundofApplication Alo- Bromus Setaria Ama- Datura Poly- Sola- ~pq preparationrate (g/ha) pecurus ranthus gonum num o example No. ~. D

128 250 95 60 - 100 - 95 loo 129 125 60 50 70 100 - 9S 100 ~ r 131 30 90 70 70 - 9S 50 90 l '

Claims (9)

claims

1. Sulfonylamino(thio)carbonyltriazolin(ethi)one having aryloxy or arylthio substituents of the general formula(I) (I) in which Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Q3 represents oxygen or sulfur, R1 represents hydrogen, hydroxyl, amino, alkylidenamino or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R2 represents substituted aryl when Q3 represents oxygen and represents optionally substituted aryl when Q3 represents sulfur and R3 represents a respectively optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, and salts of compounds of the formula (I).

2. Compounds of the formula (I) according to claim 1, characterized in that Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Q3 represents oxygen or sulfur, R1 represents hydrogen, hydroxyl, amino, C1-C6-alkylidenamino, optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl-or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkyl, represents respectively optionally fluorine-, chlorine- and/or bromine-substituted C2-C6-alkenyl or C2-C6-alkinyl, represents respectively optionally fluorine- and/or chlorine-substituted C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C4-alkyl)-amino or C1-C4-alkanoylamino, represents respectively optionally fluorine-, chlorine-, bromine- and/or C1-C4-alkyl-substituted C3-C6-cycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy- and/or C1-C4-alkoxycarbonyl-substituted phenyl or phenyl-C1-C4-alkyl, R2, in the case where Q3 represents oxygen, represents phenyl or naphthyl, each of which is substituted by cyano, carboxy, halogen, by C1-C4-alkyl (which is optionally substituted by cyano, halogen or C1-C4-alkoxy), by C1-C4-alkoxy, C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl or C1-C4-alkylthio (each of which is optionally substituted by cyano or halogen), by C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl (each of which is optionally substituted by cyano, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy and/or C1-C4-halogenoalkoxy), and, in the case where Q3 represents sulfur, represents phenyl or naphthyl, each of which is optionally substituted by cyano, carboxy, halogen, by C1-C4-alkyl (which is optionally substituted by cyano, halogen or C1-C4-alkoxy), by C1-C4-alkoxy, C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl or C1-C4-alkylthio (each of which is optionally substituted by cyano or halogen), by C3-C6-cycloalkyl, phenyl or phenyl-C1-C4-alkyl (each of which is optionally substituted by cyano, halogen, C1-C4-alkyl, C1-C4-halogenoalkyl, C1-C4-alkoxy and/or C1-C4-halogenoalkoxy), R3 represents the grouping in which R4 and R5 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C1-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, C1-C4-alkoxy-carbonyl, 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-alkylsulfinyl, C1-C4-alkylsulfonyl, di-(C1-C4-alkyl)-aminosulfonyl, C3-C6-cycloalkyl or phenyl), represents C2-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, carboxy or phenyl), represents C2-C6-alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, carboxy or phenyl), represents C1-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, C1-C4-alkoxy-carbonyl,C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl), represents C1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxy, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl), represents C2-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), represents C2-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or C1-C4-alkoxycarbonyl), C3-C6-alkinyloxy, C3-C6-alkinylthio or represents the radical -S(O)p-R6 where, p represents the numbers 1 or 2 and R6 represents C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), C3-C6-alkenyl, C3-C6-alkinyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkylamino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenyl or represents the radical -NHOR7 where R7 represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl or di-(C1-C4-alkyl)-amino-carbonyl), represents C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alkinyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl, phenyl-C1-C2-alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl), represents benzhydrol or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C1-C2-fluoroalkoxy, C1-C4-alkylthio, trifluoromethylthio or C1-C4-alkoxy-carbonyl), R4 and/or R5 furthermore represent phenyl or phenoxy, represent C1-C4-alkyl-carbonylamino, C1-C4-alkoxy-carbonylamino, C1-C4-alkylamino-carbonyl-amino, di-(C1-C4-alkyl)-amino-carbonylamino, or represent the radical -CO-R8 where R8 represents hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy,C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-alkoxyamino, C1-C4-alkoxy-C1-C4-alkylamino or di-(C1-C4-alkyl)-amino (each of which are optionally substituted by fluorine and/or chlorine), R4 and/or R5 furthermore represent trimethylsilyl, thiazolinyl, C1-C4-alkyl-sulfonyloxy, di-(C1-C4-alkyl)-aminosulfonylamino or represent the radical -CH=N-R9 where R9 represents optionally fluorine-, chlorine-, cyano-, carboxy-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulfinyl-, or C1-C4-alkylsulfonyl-substituted C1-C6-alkyl, represents optionally fluorine- or chlorine-substituted benzyl, represents optionally fluorine- or chlorine-substituted C3-C6-alkenyl or C3-C6-alkinyl, represents optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, represents optionally fluorine- and/or chlorine-substituted C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or benzyloxy, represents amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C1-C4-alkyl-carbonyl-amino, C1-C4-alkoxy-carbonylamino, C1-C4-alkyl-sulfonylamino or represents optionally fluorine-, chlorine-, bromine- or methyl-substituted phenylsulfonylamino, furthermore R3 represents the radical in which R10 represents hydrogen or C1-C4-alkyl, R11 and R12 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxy, C1-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C1-C4-alkylsulfonyl or di-(C1-C4-alkyl)-aminosulfonyl;

furthermore R3 represents the radical in which R13 and R14 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine) or C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine);

furthermore R3 represents the radical in which R15 and R16 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), represents C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl (each of which is optionally substituted by fluorine and/or chlorine), represent aminosulfonyl, mono-(C1-C4-alkyl)-aminosulfonyl, represent di-(C1-C4-alkyl)-aminosulfonyl or C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl;

furthermore R3 represents the radical in which R17 and R18 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl (which is optionally substituted by fluorine and/or bromine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), represents C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C1-C4-alkyl)-aminosulfonyl;

furthermore R3 represents the radical in which R19 and R20 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkylthio, C1-C4-alkylsulfinyl or C1-C4-alkylsulfonyl (each of which are optionally substituted by fluorine and/or chlorine), di-(C1-C4-alkyl)-amino-sulfonyl, C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl, and A represents oxygen, sulfur or the grouping N-Z1 where Z1 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), C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl or di(C1-C4-alkyl)-aminocarbonyl;

furthermore R3 represents the radical in which R21 and R22 are identical or different and each represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, Y1 represents sulfur or the grouping N-R23 where R23 represents hydrogen or C1-C4-alkyl;

furthermore R3 represents the radical in which R24 represents hydrogen, C1-C4-alkyl, benzyl, pyridyl, quinolinyl or phenyl, R25 represents hydrogen, halogen, cyano, nitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C1-C4-alkoxy-carbonyl and R26 represents hydrogen, halogen or C1-C4-alkyl, and also 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)-sulfonium, C5- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-benzyl-ammonium salts thereof.

3. Compounds of the formula (I) according to claim 1, characterized in that Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Q3 represents oxygen or sulfur, R1 represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, represents respectively optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents respectively optionally fluorine-, chlorine-, bromine-, cyano-, methyl-, trifluoromethyl- or methoxy-substituted benzyl or phenyl, R2, in the case where Q3 represents oxygen, represents cyano-, carboxy-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butyloxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, methylthio-, ethylthio-, cyclopentyl-, cyclohexyl-, phenyl- or benzyl-substituted phenyl, and, in the case where Q3 represents sulfur, represents optionally cyano-, carboxy-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butyloxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, methylthio-, ethylthio-, cyclopentyl-, cyclohexyl-, phenyl-or benzyl-substituted phenyl, R3 represents the radical in which R4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n or i-butoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy, 1,1,2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, methylthio, ethylthio, n- or i-propylthio, n- or i-butylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy, methylsulfinyl, ethylsulfonyl, methylsulfonyl, ethylsulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N-methylaminosulfonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and R5 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl;

furthermore R3 represents the radical in which R10 represents hydrogen, R11" represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl and R12 represents hydrogen;

furthermore R3 represents the radical in which R represents methyl, ethyl, n- or i-propyl, or R3 represents the radical in which R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, R25 represents hydrogen, fluorine, chlorine or bromine, R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.

4. Process for preparing compounds of the formula (I) according to claim 1 and salts thereof, characterized in that (a) triazolin(ethi)ones of the general formula (II) (II) in which Q1, Q3, R1 and R2 are each as defined in claim 1 are reacted with sulfonyl iso(thio)cyanates of the general formula (III) R3-SO2-N=C=Q2 (III) in which Q2 and R3 are each as defined in claim 1, 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) (IV) in which Q1, Q2, Q3, R1 and R2 are each as defined above and Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted with sulfonamides of the general formula (V) R3SO2-NH2 (V) in which R3 is as defined above, 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) (II) in which Q1, Q3, R1 and R2 are each as defined above are reacted with sulfonamide derivatives of the general formula (VI) R3-SO2-NH-CQ2-Z (VI) in which Q2 and R3 are each as defined above and Z represents halogen, alkoxy, aralkoxy or aryloxy, 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) (II) in which Q1, Q3, R1 and R2 are each as defined above are reacted with sulfonyl halides of the general formula (VII) R3-SO2-X (VII) in which R3 is as defined above and X represents halogen, and metal (thio)cyanates of the general formula (VIII) MQ2CN (VIII) in which Q2 is as defined 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, and the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are, if required, converted into salts by customary methods.

5. Herbicidal compositions, characterized by a content of at least one compound of the formula (I) or a salt thereof according to claim 1.

6. Use of compounds of the general formula (I) or of salts thereof according to claim l for controlling undesirable vegetation.

7. Method for controlling weeds, characterized in that compounds of the general formula (I) or salts thereof according to claim 1 are allowed to act on the weeds or their habitat.

8. Process for preparing herbicidal compositions, characterized in that compounds of the general formula (I) or salts thereof according to claim 1 are mixed with extenders and/or surfactants.

9. Triazolin(ethi)one derivatives of the general formula (IV) (IV) in which Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Q3 represents oxygen or sulfur, R1 represents hydrogen, hydroxyl, amino, alkylidenamino or represents a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R2 represents substituted aryl when Q3 represents oxygen and represents optionally substituted aryl when Q3 represents sulfur and Z represents halogen, alkoxy, aralkoxy or aryloxy.