CA2333068A1 - Sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents - Google Patents

Abstract

The invention relates to novel sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents of formula (I) in which Q1 represents oxygen or sulfur; Q2 represents oxygen or sulfur; R1 represents hydrogen, amino, alkylidene amino or a respective optionally substituted radical from the series of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkyl amino, dialkyl amino, alkanoyl amino, cycloalkyl, cycloalkyl alkyl, cycloalkyl amino, aryl and aryl alkyl; R2 optionally represents substituted alkenyl; R3 represents a respective optionally substituted radical from the series of alkyl, aryl alkyl, aryl and heteroaryl. The invention also relates to salts of the compounds of formula (I), to methods, to novel intermediate products for producing compounds of formula (I), and to the use thereof as herbicides and/or fungicides.

Description

Le A 32 998-Foreign Countries Sulphonylamino(thio)carbonyltriazolin(ethi)ones with alkenyl substituents The invention relates to new sulphonylamino(thio)carbonyltriazolin(ethi)ones with alkeny( substituents, to a plurality of processes and novel intermediates for their preparation, and to their use as plant treatment agents, in particular as herbicides and as fungicides.
It has already been disclosed that certain sulphonylamino(thio)carbonyltriazolin-(ethi)ones have herbicidal properties (cf. EP 341489, EP 422469, EP 425948, EP
431291, EP 507171, WO 96122982). However, the action of these prior-art compounds is not satisfactory in all respects.
There have now been found the new sulphonylamino(thio)carbonyltriazolin-(ethi)ones with alkenyl substituents of the general formula (I) Q~
Rs Q2 R' SOz - N N N
H N ~ CI) in which Q 1 represents oxygen or sulphur, Q2 represents oxygen or sulphur, Rl represents hydrogen, amino, alkylideneamino, or a radical from the series alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and aryl-alkyl, in each case optionally substituted, Le A 32 998-Foreign Countries R2 represents optionally substituted alkenyl and R3 represents a radical from the series alkyl, aralkyl, aryl and heteroaryl, in each case optionally substituted, and salts of compounds of the formula (I).
The new sulphonylamino(thio)carbonyltriazolin(ethi)ones with alkenyl substituents of the general formula (I) are obtained when (a) triazolin(ethi)ones of the general formula (II) Q' H,N~N,Ri (II) in which Q l, R 1 and R2 have the abovementioned meanings are reacted with sulphonyliso(thio)cyanates of the general formula (III) R3-S02-N=C=Q2 (III) in which Q2 and R3 have the abovementioned meanings, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, Le A 32 998-Foreign Countries or when (b) triazolin(ethi)one derivatives of the general formula (IV) Q2 Q, R' ~N~N
Z ~ ~ (IV) in which Ql Q2~ R1 and R2 have the abovementioned meanings and Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted with sulphonamides of the general formula (V) I S R3-S02-NH2 (V) in which R3 has the abovementioned meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when (c) triazolin(ethi)ones of the general formula (II) Le A 32 998-Foreign Countries Q' H_N~N,R~
(II) in which Q l , R 1 and R2 have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (VI) R3-S02-NH-CQ2-Z (VI) in which Q2 and R3 have the abovementioned meanings 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 when (d) triazolin(ethi)ones of the general formula (II) Q' H_N~N,R' _~ (II) N Rz in which Le A 32 998-Foreign Countries Q1, R1 and R2 have the abovementioned meanings are reacted with sulphonyl halides of the general formula (VII) R3-S02-X (VII) in which R3 is as defined above and X represents halogen and with metal (thio)cyanates of the general formula (VIII) I S MQ2CN (VIII) in which Q2 is as defined above and M represents an alkali metal or alkaline earth metal equivalent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are converted into salts by customary methods.
The new sulphonylamino(thio)carbonyltriazolin(ethi)ones with alkenyl substituents of the general formula (I) have interesting biological effects; in particular, they are distinguished by a potent herbicidal and/or fungicidal activity.

Le A 32 998-Foreign Countries The following applies to the definitions in formula (I):
R1 preferably represents hydrogen, amino, C1-C6-alkylideneamino, or represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-alkylcarbonyl or Cl-C4-alkoxycarbonyl, or represents C2-C6-alkenyl or C2-C6-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents Cl-C6-alkyl-oxy or C2-C6-alkenyloxy, or represents Cl-C6-alkylamino, di-(C1-C4-alkyl)-amino or Cl-C4-alkyl-carbonylamino, each of which is optionally substituted by fluorine and/or chlorine, or represents C3-C6-cycloalkyl or C3-C6-cyclo-alkyl-C1-C4-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine and/or C 1-C4-alkyl, or represents phenyl or phenyl-C 1-C4-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy and/or C1-C4-alkoxy-carbonyl.
R2 preferably represents C2-C6-alkenyl which is optionally substituted by cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl.
_ R5 R3 preferably represents the group where Ra R4 and RS are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C 1-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxycarbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-Le A 32 998-Foreign Countries amino-carbonyl, C1-C4-alkoxy, C1-C4-alkyl-carbonyloxy, C1-C4-alkoxy-carbonyloxy, C1-C4-alkylamino-carbonyloxy, C1-C4-alkyl-thio, C1-C4-alkylsulphinyl, Cl-C4-alkylsulphonyl, di-(Cl-C4-alkyl)-aminosulphonyl, C3-C6-cycloalkyl or phenyl), or represents C2-C6-S alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl or phenyl), or represents C2-C6-alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl or phenyl), or represents Cl-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, Cl-C4-alkoxy, C1-C4-alkylthio, Cl-C4-alkylsulphinyl, Cl-C4-alkylsulphonyl or C3-C6-cycloalkyl), or represents C1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represents C2-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C 1-C4-alkoxy-carbonyl), or represents C2-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or C1-C4-alkoxy-carbonyl), or represents C3-C6-alkinyloxy, C3-C6-alkinylthio or 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-Le A 32 998-Foreign Countries _g_ C1-C4-alkylamino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenyl or the radical -NHOR~ where R~ represents C 1-C 12-alkyl (which is optionally substituted by fluorine, chlorine, 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), or represents C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), or represents 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), or represents diphenylmethyl, or represents phenyl (which is 1 S optionally substituted by fluorine, chlorine, nitro, cyano, C 1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C1-C2-fluorine-alkoxy, C1-C4-alkylthio, trifluoromethylthio or C1-C4-alkox_~-carbonyl), R4 and/or RS furthermore represent phenyl or phenoxy, or represent C 1-C4-alkyl-carbonylamino, C1-Cq-alkoxy-carbonylamino, C1-C4-alkyl-amino-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-alkyl-thio, C1-C4-alkylamino, C1-C4-alkoxyamino, C1-C4-alkoxy-Le A 32 998-Foreign Countries C1-C4-alkyl-amino or di-(C1-C4-alkyl)-amino (which are optionally substituted by fluorine and/or chlorine), R4 and/or RS furthermore represent trimethylsilyl, thiazolinyl, 1,2,4-oxa-diazol-5-yl, 3-methyl-1,2,4-oxadiazol-5-yl, 1,3-dioxolan-2-yl, C1-C4-alkylsulphonyloxy, di-(C1-C4-alkyl)-aminosulphonylamino or represent the radical -CH=N-R9 where R9 represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C3-C6-alkenyl or C3-C6-alkinyl which are optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, trifluoromethyl, tri-fluoromethoxy or trifluoromethylthio, or represents C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or benzyloxy, which are optionally substituted by fluorine and/or chlorine, or represents amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C1-C4-alkyl-carbonylamino, C1-C4-alkoxy-carbonylamino, C1-C4-alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl.
R3 furthermore preferably Le A 32 998-Foreign Countries ,o R R, 2 represents the radical _CH
R"
where R l 0 represents hydrogen or C 1-C4-alkyl, R 1 l and R 12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, Cl-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), Cl-C4-alkoxy (which is optionally substituted by fluorine and/ or chlorine), carboxyl, C1-C4-alkoxy-carbonyl, dimethylamino-carbonyl, C1-C4-alkylsu(phonyl or di-(Cl-C4-alkyl)-amino-sulphonyl.
R3 furthermore preferably represents the radical R~3 ~ ~ R,a \ \
where R 13 and R 14 are identical or different and 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).

Le A 32 998-Foreign Countries R3 furthermore preferably R~s represents the radical \N Ris where R 15 and R 16 are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C1-C4-alkylthio, C1-C4-alkylsulphinyl or C 1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(Cl-C4-alkyl)-aminosulphonyl, or represent di-(C1-C4-alkyl)-aminosulphonyl or Cl-C4-alkoxy-carbonyl or dimethylamino-carbonyl.
R3 furthermore preferably represents the radical Rig N
where R 1 ~ and R 18 are identical or different and represent hydrogen, fluorine, chlorine, bromine, Cl-C4-alkyl (which is optionally Le A 32 998-Foreign Countries substituted by fluorine and/or bromine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C 1-C4-alkylthio, C 1-C4-alkylsulphinyl or C 1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C1-C4-alkyl)-amino-sulphonyl.
R3 furthermore preferably R' 9 represents the radical I ' ~ RZo A
where R19 and R20 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C 1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), Cl-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), di-(Cl-C4-alkyl)-amino-sulphonyl, C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl, and A represents oxygen, sulphur or the group N-T where T represents hydrogen, Cl-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-C6-cycloalkyl, benzyl, phenyl (which is optionally Le A 32 998-Foreign Countries substituted by fluorine, chlorine, bromine or nitro), Cl-C4-alkylcarbonyl, C 1-C4-alkoxy-carbonyl or di-(C 1-C4-alkyl)-aminocarbonyl.
S R3 furthermore preferably Rzi represents the radical I N Rzz Y
where R21 and R22 are identical or different and represent hydrogen, Cl-C4-alkyl, halogen, C 1-C4-alkoxy-carbonyl, C 1-C4-alkoxy or C I -C4-halogenoalkoxy, Y I represents sulphur or the group N-R23 where R23 represents hydrogen or C 1-C4-alkyl.
R3 furthermore preferably Rzs Rzs represents the radical N
Rza where Le A 32 998-Foreign Countries R24 represents hydrogen, Cl-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 Cl-C4-alkoxy-carbonyl, and R26 represents hydrogen, halogen or Cl-C4-alkyl.
The invention furthermore preferably relates to sodium, potassium, magnesium, calcium, ammonium, C 1-Cq.-alkyl-ammonium, di-(C 1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-ammonium, tetra-(CI-C4-alkyl)-ammonium, tri-(CI-C4-alkyl)-sulphonium, CS- or C6-cycloalkyl-ammonium and di-(CI-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which Q1, Q2, R1, R2 and R3 have the meanings given above as being preferred.
R 1 in particular represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents methoxy, ethoxy, n- or i-propoxy, or represents allyloxy, or represents methylamino, ethyl-amino, n- or i-propylamino, dimethylamino or diethylamino, or represents cyclopropyl which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl.
R2 in particular represents ethenyl, propenyl or butenyl, each of which is optionally substituted by cyano, fluorine, chlorine and/or bromine.

Le A 32 998-Foreign Countries R3 in particular represents the radical Ra where R4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-fluoro-ethoxy, 2,2-difluoro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy, 1,1,2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, cyclopropylmethoxy, methyl-thio, ethylthio, n- or i-propylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy, methoxy-carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl and RS represents hydrogen, fluorine, chlorine, bromine methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro-methoxy, trifluoromethoxy, methylthio or ethylthio.
R3 furthermore represents in particular R"
R~z the radical -~H
Rio where Le A 32 998-Foreign Countries R 10 represents hydrogen, R 11 represents fluorine, chlorine, bromine, methyl, methoxy, di-fluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl R 12 represents hydrogen.
Furthermore, R3 represents in particular the radical ~J
RO-~ S
O
where R represents methyl, ethyl, n- or i-propyl.
R3 furthermore represents in particular the radical R2s R2s I I
,N
N
'R za where R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, R25 represents hydrogen, fluorine, chlorine or bromine and Le A 32 998-Fore~n Countries R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxy-carbonyl.
The definitions of radicals mentioned above, either in general or preferred ranges, apply not only to the end product of the formula (I) but also, correspondingly, to the starting materials or intermediates required in each case for preparation.
These definitions of radicals can be combined with each other as desired, that is to say combinations between the indicated ranges of preferred compounds are also possible.
Preferred in accordance with the invention are those compounds of the formula (I) where a combination of the meanings mentioned above as being preferred exists.
Particularly preferred in accordance with the invention are those compounds of the formula (I) where a combination of the meanings mentioned above as being I 5 particularly preferred exists.
The hydrocarbon radicals mentioned in the definitions of the radicals, such as alkyl., alkenyl or alkinyl, also in combination with hetero atoms such as in alkoxy, alkylthio or alkylamino, can be straight-chain or branched, even in those cases where this ~, not expressly specified.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Cis/trans isomerism can occur in certain compounds of the formula (I) according to the invention. In these cases, the invention extends to both of each of the geometric isomers and also their mixtures (in any weight ratios).
If, for example, 2-trifluoromethoxy-phenyl sulphonyl-isocyanate and 4-ethyl-5-(2-fluoro-propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (trans isomer) are used as Le A 32 998-Foreign Countries starting materials, the course of the reaction in process (a) according to the invention can be outlined by the following formulaic scheme:
O

H,N~N,C2H5 \ ~ + ' F
SOZ-N=C=O N

O O
SO~ ~ N ~ N ~C2H5 F
H CHs If, for example, 2-ethylthio-benzenesulphonamide and 2-chlorocarbonyl-4-cyclo-propyl-5-(1,2-dichloro-propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (traps iso-mer) are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined by the following formulaic scheme:
O O
S-C2Hs ~
+ ~N~N~
\ CI ~ CI

CI CHs S-CzHs O O
- HCI \ ~ ~
S02-~ ~N~N~
- CI
CI CHs Le A 32 998-Foreign Countries If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-(I-bromo-propen-2-yl)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (trans isomer) are used as starting materials, the course of the reaction in process (c) according to the invention can be outlined by the following formulaic scheme:
O
O-CHs H,N~N,CH3 - H

H3C Br O O
SO~ ~ N ~ N , CH3 H3C Br If, for example, 2-chloro-6-methyl-benzenesulphonyl chloride, 4-allyl-5-(propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (trans isomer) and sodium cyanate are used as I O starting material, the course of the reaction in process (d) according to the invention can be outlined by the following formulaic scheme:

Le A 32 998-Foreign Countries O
/ CH3 H , N ~ N , CH2 CH=CH2 \ I + N_ H
SOz-CI

+ NaOCN ~ I O O
'~ \
- NaCI S02 ~ N N N - CHz-CH=CH2 CI H N - H

Formula (II) provides a general definition for the triazolin(ethi)ones to be used as starting materials in processes (a), (c) and (d) according to the invention for the preparation of compounds of the formula (I).
In formula (II), QI, R1 and R2 preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred or particularly preferred for Q1, R1 and R2.
The triazolin(ethi)ones of the general formula (II) were hitherto not known from the literature; being new substances, they are also subject-matter of the present application.
The new triazolin(ethi)ones of the general formula (II) are obtained when (a) iso(thio)cyanates of the general formula (IX) Q 1=C=N-R 1 (IX) in which Le A 32 998-Foreign Countries Q 1 and R 1 have the abovementioned meanings are reacted with hydrazides of the general formula (X) H2N-NH-CO-R2 (X) in which R2 has the abovementioned meaning at temperatures between 0°C and 100°C, if appropriate in the presence of diluents, such as, for example, isopropanol or water, if appropriate in the presence of a reaction auxiliary such as, for example, sodium hydroxide [during which process isomerization may take place due to a double-bond shift] and the product is worked up in the customary manner (cf. the Preparation Examples), or when (~3) (thio)semicarbazides of the general formula (XI) H2N-NH-CQ 1-NH-R 1 (XI) in which R 1 and Q 1 have the abovementioned meanings are reacted with carboxylic acids or their derivatives of the general formula (XII) R2-CO-Y (XII) Le A 32 998-Foreign Countries in which R2 has the abovementioned meaning and Y represents hydroxyl, halogen or the group -0-CO-R2 at temperatures between 0°C and 100°C, if appropriate in the presence of a diluent such as, for example, sulpholane, if appropriate in the presence of a reaction auxiliary such as, for example, sodium hydroxide, and if appropriate in the presence of a stabilizer such as, for example, hydroquinone, and the product is worked up in the customary manner (cf. the Preparation Examples).
Formula (III) provides a general definition of the sulphonyliso(thio)cyanates furthermore to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
In formula (III), Q2 and R3 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being 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).
Formula (IV) provides a general definition of the triazolin(ethi)one derivatives to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I). In formula (IV), Ql, Q2, R1 and Le A 32 998-Foreign Countries preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as being preferred or particularly preferred for Ql, Q2, Rl and R2; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.
The starting materials of the formula (IV) were hitherto not known from the literature; being novel substances, they are also subject-matter of the present application.
The new compounds of the formula (IV) are obtained when triazolin(ethi)ones of the general formula (II) Q, H~N~N~R~ (II) N

in which Q l, R 1 and R2 have the abovementioned meaning are reacted with carbonic acid derivatives of the general formula (XIII) Z-CQ2-Z 1 (XIII) in which Q2 and Z have the abovementioned meanings and Z 1 represents halogen (in particular chlorine), alkoxy (in particular methoxy), aralkoxy (in particular benzyloxy) or aryloxy (in particular phenoxy) Le A 32 998-Foreign Countries at temperatures between 0°C and 100°C, if appropriate in the presence of an acid acceptor such as, for example, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium t-butoxide or potassium t-butoxide and, if appropriate, 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.
Formula (V) provides a general definition of the sulphonamides furthermore to be used as starting materials in process (b) according to the invention for the preparation of the compound of the general formula (I). In formula (V), R3 preferably, or in particular, has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) as being preferred or particularly preferred for R3.
The starting materials of the formula (V) 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).
Formula (VI) provides a general definition of the sulphonamide derivatives to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the formula (I). In formula (VI), Q2 and R3 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as being preferred or particularly preferred for Q2 and R3; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.

Le A 32 998-Foregn Countries The starting materials of the formula (VI) are known and/or can be prepared by processes known per se.
Formula (VII) provides a general definition of the sulphonyl halides to be used as starting materials in process (d) according to the invention for the preparation of the compounds of the formula (I). In formula (VII), R3 preferably, or in particular, has the meaning which has already been described above in connection with the description of the compounds of the formula (I) as being preferred or particularly preferred for R3; X preferably represents fluorine, chlorine or bromine, in particular chlorine.
The starting materials of the formula (VII) are known and/or can be prepared by processes known per se.
The new intermediates of the above formulae (II) and (IV), which only differ by the fact that the 2-position is unsubstituted or substituted by an acyl radical -CQ2-Z, can be summarized by the following formula (XIV):
Q' A'N~N'R (XIV) N=

in which R1, R2 and Q1 have the meanings given above under formula (I) and A represents hydrogen or the group -CQ2-Z where Le A 32 998-Foreign Countries _ 2(~ _ Q2 has the meaning given above under formula (I) and Z represents halogen, alkoxy, aralkoxy or aryloxy.
What has been said above for the compounds of the formulae (II) and (IV) also applies to the preferred and especially preferred meanings of all variable radicals of the formula (XIV).
Processes (a), (b), (c) and (d) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out using diluents.
Suitable diluents are virtually all inert organic solvents. These preferably include 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, dibutyl ether, glycol dimethyl ether, 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 such as, for example, acetonitrile and propionitrile; amides such as, for example, dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
Reaction auxiliaries or acid acceptors which can be employed in processes (a), (b), (c) and (d) according to the invention are all acid-binding agents which can conventionally be employed for such reactions. The following are preferably suitable: alkali metal hydroxides such as, for example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as, for example, calcium hydroxide, alkali metal carbonates and alkali metal alkoxides such as sodium carbonate, potassium carbonate, sodium tert-butoxide and potassium tert-butoxide, furthermore basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiiso-Le A 32 998-Foreign Countries propylamine, 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 processes (a), (b), (c) and (d) according to the invention can be carried out within a substantial range. In general, the processes are carried out at temperatures between -20°C and +100°C, preferably at temperatures between 0°C
and +80°C.
In general, processes (a), (b), (c) and (d) according to the invention are carried out under atmospheric pressure. However, the processes can also be carried out under elevated or reduced pressure.
To carry out processes (a), (b), (c) and (d) according to the invention, the starting materials required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use a larger excess of one of the components employed in each case. In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Work-up in processes (a), (b), (c) and (d) according to the invention is carried out in each case by customary methods (c~
the Preparation Examples).
If appropriate, salts may be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base. The salts can then be isolated by concentration or filtration with suction, if appropriate after prolonged stirring.

Le A 32 998-Foreign Countries The active compounds according to the invention can be employed as defoliants, desiccants, haulm killers and, in particular, as weedkillers. Weeds in the broadest sense are to be understood as all plants which grow in locations where they are undesired. Whether substances according to the invention act as total or selective herbicides depends essentially on the amount used.
For example, the active compounds according to the invention can be used in 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, Taraxacum.
Dicotyledonous crops of the_genera~ Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocotyledonous weeds of the genera' 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, Apera.
Monocotyledonous crops of the ~enera~ Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus, Allium.

Le A 32 998-Foreign Countries However, the use of the active compounds according to the invention is restricted in no way to these genera but also extends in the same manner to other compounds.
Depending on the concentration, the compounds are suitable for total weed control, S for example on industrial terrain and rail tracks, and on paths and areas with or without tree stands. Equally, the compounds can be employed for controlling weeds in perennial crops, for example forests, ornamental 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 pastures, and for selective weed control 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- and post-emergence.
In addition, the active compounds according to the invention also have a potent microbicidal action and can be employed in practice for controlling undesired microorganisms. Thus, the active compounds are suitable, in suitable concentrations, for use as fungicides and/or bactericides.
Fungicides are employed in crop protection for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
Bactericides are employed in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Some pathogens which cause fungal and bacterial diseases and which come under the generic terms indicated above may be mentioned by way of example, but not by limitation:

Le A 32 998-Foreign Countries Xanthomonas species, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv.
Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea Le A 32 998-Foreign Countries (Conidial form: Drechslera, syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliobolus sativus (Conidial form: Drechslera, syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondite;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nude or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;

Le A 32 998-Foreign Countries Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
The good tolerance by plants of the active compounds required for controlling plant diseases allows aerial parts of the plants, propagation material and seed, and the soil, to be treated.
The active compounds according to the invention can therefore be employed with good success for controlling diseases in fruit and vegetable production such as, for example, against Podosphaera species, and for controlling rice diseases, such as, for example, Pyricularia oryzae (protective and systemic use).
The active compounds can be converted into the customary formulations, such as I S solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations 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 surfactants, that is emulsifiers and/or dispersants and/or foam-formers.
If water is used as an extender, organic solvents can, for example, also be used as cosolvents. Liquid solvents which are mainly suitable are: 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 Le A 32 998-Foreign Countries ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and water.
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 highly disperse silica, alumina and silicates; suitable solid Garners for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks;
suitable emulsifiers and/or foam formers 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 and protein hydrolysates; suitable dispersants 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 latexes such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else 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 dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

Le A 32 998-Foreign Countries 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 mixes or tank mixes being possible.
Possible components for the mixtures are known herbicides, such as, for example, acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium), bromobutide, bromo-fenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlor-imuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulf uron(-methyl), cloransulam(-methyl), cumyluron, cyanazine, cycloate, cyclosulfam-uron, cycloxydim, cyhalofop(-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, di-allate, dicamba, diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat, diflu-fenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, di-methenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), etho-fumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, fluazifop(-P-butyl), flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flur-pyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl), flur-primidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxaflutole, isoxapyrifop, lactofen, len-acil, linuron, mcpa, mcpp, mefenacet, metamitron, metazachlor, methabenzthiazuron, Le A 32 998-Foreign Countries metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metri-buzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxa-sulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, propyzamide, pro-sulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyraz-oxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-p-ethyl), quizalofop(-P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, terbuthyl-azine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, tri-allate, triasulfuron, triben-uron(-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.
Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners, 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 manner, for example by watering, spraying, atomizing or spreading.
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 application rates are Le A 32 998-Foreign Countries between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the examples which follow.

Le A 32 998-Foreign Countries Preparation Examples:
Example 1 F2HC, 1 / O O
O
SO . ~N~N~CH3 z N
H N-(Process (a)) A mixture of 1.4 g (10 mmol) of 4-methyl-5-(propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one [trans isomer (II-1)], 3.0 g (12 mmol) of 2-difluoromethoxy-phenyl sulphonylisocyanate and 40 ml of acetonitrile is stirred for 15 hours at room temperature (approx. 20°C) and then concentrated in a water pump vacuum. The residue is stirred with isopropanol/petroleum ether and the crystalline product is isolated by filtration with suction.
This gives 3.7 g (95% of theory) of 2-(2-difluoromethoxy-phenylsulfonylamino-carbonyl)-4-methyl-5-(propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one [trans form]
of melting point 173°C.
Example 2 H3C~N~SOz SO . ~ N ~ N ~ CH3 z N
H N-(Process (b)) Le A 32 998-Foreign Countries 2.64 g (10 mmol) of N,N-dimethyl-benzene-1,2-disulfonamide are taken up in 30 ml of toluene and the mixture is treated at room temperature (approx.
20°C) with 1.52 g (10 mmol) of 1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU). The mixture is stirred for 30 minutes at room temperature, and a solution of 2.6 g (10 mmol) of 4-methyl-phenoxycarbonyl-5-(propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one [isomer mix-ture: 70% trans/30% cis] in 25 ml of acetonitrile is then added dropwise. The reaction mixture is stirred for 4 hours at room temperature and subsequently concentrated in a water pump vacuum. The residue is shaken with methylene chloride and 2 N hydrochloric acid, and the organic phase is separated off, dried with sodium sulphate and filtered. The filtrate is concentrated in a water pump vacuum, the residue is stirred with ethyl acetate/petroleum ether, and the crystalline product is isolated by filtration with suction.
This gives 2.5 g (58% of theory) of 2-(2-dimethylaminosulfonyl-phenylsulfonyl-aminocarbonyl)-4-methyl-5-(propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 163°C [as isomer mixture: 72% trans/28% cis].
Other examples of compounds of the formula (I) which can be prepared analogously to Preparation Examples 1 and 2 and in accordance with the general description of the preparation method according to the invention are those listed in Table 1 below.

S02. N N N ~ R (I) H N -Rz Le A 32 998-Forei~~ Countries Table 1: Examples of the compounds of the formula (I) Ex, Q 1 Q2 R 1 R2 *) R3 Melting No. point (°C) 3 O O CH3 ~cH3 ~ coocH3 139 traps 4 O O CH3 ~cH ~ CF3 187 traps 5 O O CH3 ~cH3 ~ OCF3 187 traps ~ /
6 O O CH3 ~cH3 I ~ coocZHs 113 traps 7 O O CH3 '~%~cH3 ~ cooc,H, 109 i traps 8 O O CH3 ~cH3 ~ OCH3 171 traps ~ /

9 O O CH3 ~cH ~ OCZHS 147 traps /

10 O O CH3 ~cH ~ Br 197 traps /

11 O O CH3 ~cH3 ~ SCH3 146 traps 12 O O CH3 ~cH3 ~ Sc2H5 169 traps /

Le A 32 998-Foreign Countries Table 1: (continued) Ex. Q1 Q2 R1 R2 *) R3 Melting No. point (°C) 13 O O CH3 ~cH ~ CI 212 trans /

14 O O CH3 ~cH3 ~ CHs 192 trans 15 O O CH3 ~cH3 ~ CH3 193 trans CI

16 O O CH3 ~cH3 H3C ~ CH3 156 i trans 17 O O CH3 ~cH3 ~ NOZ 147 trans/cis 70:30 18 O O CH3 ~CH HsC~N~oCHs 134 trans/cis 72:28 19 O O CH3 ~cH ~ CF3 162 trans/cis /
66,5:33,5 20 O O CH3 ~cH3 I ~ o~ 110 i trans/cis 70:30 Le A 32 998-Foreign Countries Table 1: (continued) Ex. QI Q2 RI R2 *) R3 Melting No. point (C) 21 O O CH3 ~cH3 ~ 1 I S
"3 N

I
N

tranS/C1S ~

~ ~

74:26 22 O O ~ NCH ~ 126 3 coocH3 traps 23 O O ~ ~~H I 140 3 ~

traps 24 O O ~ ~CH3 ~ 146 traps ~5 O O ~ ~cH I 113 3 ~
oCHF2 traps 26 O O ~ ~CH3 ~ 120 cooc2H5 i traps 27 O ~CH3 ~ 117 COOC3H~

traps 28 O O ~ ~cH ~ 178 traps /

29 O O ~ ~cH I 153 3 ~

traps /

30 O O ~ NCH ~ 173 3 Br traps Le A 32 998-Foreign Countries Table 1: (continued) Ex. Q 1 Q2 R 1 R2 *) R3 Melting No. point (°C) 31 O O ~ ~~H3 ~ ~ SCH3 143 trans /
32 O O ~ ~oH3 ( ~ S~2H5 137 trans /
33 O O ~ ~oH ~ CI 174 trans 34 O O ~ ~~H ~ CH3 168 trans 35 O O ~ ~~H ~ CH3 168 trans CI
36 O O ~ ~~H3 HaC ~ CH3 183 i traps ' 37 O O CH3 ~cH3 ~ CI 184 traps CI
38 O O CH3 ~ ~ coocH3 128 i 39 O O CH3 ~ ~ OCF3 147 CH3 ~ /

Le A 32 998-Foreign Countries Table 1: (continued) Ex. Ql Q2 R1 R2 *) R3 Melting No. point (°C) 40 O O CH3 ~ ~ CF3 123 41 O O CH3 ~~ ~ Br 163 42 O O CH3 ~~ I ~ OC2H5 145 43 O O CH3 ~cH w ocH~cH,~2 146 trans 44 O O CH3 ~ coocH3 187 ~CH3 45 O O ~ ~3 ~ OCF3 166 46 O O ~ 3 ~ CF3 149 47 O O ~ CH3 ~ Br 204 48 O O ~ CH3 I ~ OC2H5 145 49 O O CH3 ~cH ~ CooCH3 119 Le A 32 998-Foreign Countries Table 1: (continued) Ex. Q 1 Q2 R 1 R2 *) R3 Melting No. point (C) 50 O O CH3 ~cH ~ OCF3 151 51 O O CH3 ~cH3 ~ CF3 130 52 O O CH3 ~cH3 ~ Br 135 53 O O CH3 ~cH3 ~ oc2H5 123 54 O O CH / ~COOCH(CH3)~122 3 ~cH3 I~-I

trans/cis 54:46 55 O O ~ ~ ~ OCH(CH~)Z143 trans S6 O O CH3 NCH ~ cH(CH3)z 154 trans/cis 64:36 ~H3 57 O O ~ ~~H3 ~ cH(cH3)z 154 trans ' 58 O O CH3 ~cH ~ ~H(cH3)z 110 trans/cis 45:55 ~ZHS

Le A 32 998-Foreign Countries Table I : (continued) Ex. Q 1 Q2 R 1 R2 *) R3 Melting No. point (°C) 59 O O ~ NCH ~ CH(CH3)z 140 trans CzHs 60 O O CH3 ~CH3 ~ CF3 172 trans/cis 77:23 Br 61 O O ~ ~~H3 ~ CF3 210 trans ~ /
Br 62 O O n-C3H7 -CH=CH2 CF3 115 *) Notes on the stereochemical data given for R2 1 ) All of the active compounds of the formula (I) prepared from the trans isomer (II-1) described hereinbelow also have the transconfiguration (termed "trans").
2) The same applies to all the active compounds (I) prepared from the trans isomer (II-4). The trans isomer (II-4) is already synthesized in a purity of >
95%; the cis isomer has not been isolated as yet.
3) In some cases, however, (II) cis/trans mixtures obtained from triazolinone (II) mother liquors were converted into the corresponding phenylurethanes (IV) Le A 32 998-Foreign Countries (also cis/trans isomer mixtures) and then reacted with sulphonamides (V) in accordance with preparation method (b) to give active compounds (I) which in this case were also cis/trans isomer mixtures of various compositions, depending on the solubility of the isomers.
In these cases, the isomer composition of the end product (I) obtained is shown as a percentage (%), determined from the 1 H-NMR spectrum in question. For example, I 0 trans/cis 72:28 means that the active compound in question has an isomer composition of 72% of the trans isomer and 28% of the cis isomer.
4) The two CH3 groups in intermediate (II-6) and also in the active compounds (I) prepared therefrom in accordance with Examples 49-53 are - as stated - in the cis position, according to 2D NMR measurement.

Le A 32 998-Foreign Countries Starting materials of the formula (II):
Example (II-I) O
H,N~N,CH3 N-283 g (4.97 mol) of methyl isocyanate are added dropwise in the course of 1 hour to a stirred, ice-cooled solution of 526 g (4.97 mol) of vinylacetohydrazide in a litre of isopropanol. The reaction mixture is stirred for a further 30 minutes at room temperature (approx. 20°C) and subsequently treated with 800 ml of water and 800 g of 50% sodium hydroxide solution, with ice-cooling. The mixture is then heated to 80°C in the course of approximately 30 minutes and refluxed for two hours. The mixture is subsequently concentrated in a water pump vacuum to approximately half its volume and neutralized with 1 kg of concentrated hydrochloric acid. It is then concentrated under reduced pressure, the residue is taken up in 1500 ml of N,N-dimethylformamide, the undissolved sodium chloride is filtered off, and the filtrate is reconcentrated under reduced pressure. The residue is distilled at approx. 1 mbar.
This gives 422 g (55% of theory) of 4-methyl-5-(propen-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one of boiling point 140°C (at 1 mbar) as a cis/trans isomer mixture [obviously formed owing to double-bond isomerization during the reaction, the (propen-3-yl) radical from the vinylacetohydrazide with its isolated, terminal double bond being isomerized to the (propen-1-yl) residue with conjugated (cis/trans) double bond].
The product solidifies (melting point: 94°C); it consists to 81.5% of the trans isomer and to 18.5% of the cis isomer. The isomer mixture can be recrystallized from Le A 32 998-Foreign Countries approximately twice the amount of ethyl acetate, in which case approx. 130 g pure traps isomer (II-1) of melting point 112°C are obtained.
Example (II-2) O
H,N~N,CH3 N-A mixture of 178 g (2.0 mol) of 4-methyl-semicarbazide, 10 g of hydroquinone and 250 ml of sulpholane is treated with 339 g (2.0 mol) of methacrylic anhydride, with ice-cooling; the reaction mixture is stirred for another 1 S minutes at room temperature (approx. 20°C), then treated with 640 g of 25% sodium hydroxide solution and stirred for two hours at 80°C. After the mixture has cooled to room temperature, it is neutralized with concentrated hydrochloric acid and concentrated under reduced pressure. The residue is extracted with toluene while hot. The product crystallizes upon cooling of the extraction solution; it is isolated by filtration with suction.
This gives 70 g (25% of theory) of 4-methyl-5-(propen-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 85°C.
Other examples of the compounds of the formula (II) which can be prepared analogously to Preparation Examples (II-1) and (II-2) are those listed in Table 2 below (as regards the stereochemical data for R2, compare the notes for the above Table 1 ).

Le A 32 998-Foreign Countries Q' H~N~N,R, (II) Table 2: Examples of the compounds of the formula (II) Ex. Q 1 R 1 R2 Physical No. data II-3 O CH3 CH3 b.p.:85C
'CH (at 0.5 mbar) II-4 O ~ ~/ 'NCH m.p.: 219C

trans II-5 O ~ CH3 m.p.:152C

_CH

II-6 O CH3 ~CH m.p.:147C

Le A 32 998-Foreign Countries Table 2: (continued) Ex. No. Q 1 R 1 R2 Physical data ~CH3 II-11 O CH3 -CH=CH2 II-12 O ~ -CH=CH2 II-13 O ~ -CH=CH2 Use Examples As regards the stereochemistry of the test compounds, what has been said for the above Table 1 also applies here Example A
Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable active compound preparation, 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 concentrarion.

Le A 32 998-Foreign Countries Seeds of the test plants are sown in normal soil. After approximately 24 hours, the soil is sprayed with the active compound preparation in such a way that the amounts of active compound desired in each case are applied per unit area. The concentration of the spray mixture is chosen in such a way that the amounts of active compound desired in each case are applied in 10001 of water/ha.
After three weeks, the degree of damage to the plants is scored in % damage in comparison with the development of the untreated control.
The figures denote:
0% - no action (like untreated control) 100% - total destruction In this test, a very potent action against weeds combined with a mostly good tolerance by crop plants such as, for example, cotton, barley, maize, oilseed rape, sunflowers, soya beans, wheat and sugar beet, is shown, for example, by the compounds of Preparation Example 3, 4, 6, 9, 10, 12, 13, 17, 19, 20, 22, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 38, 40, 43, 57 and 59.

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Le A 32 998-Foreign Countries Example B
Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable active compound preparation, 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 active compound preparation in such a way that the amounts of active compound desired in each case are applied per unit area. The concentration of the spray mixture is chosen in such a way that the amounts of active compound desired in each case are applied in of water/ha.
After three weeks, the degree of damage to the plants is scored in % damage in comparison with the development of the untreated control.
The figures denote:
0% - no action (like untreated control) 100% - total destruction In this test, a very potent action against weeds combined with a mostly good tolerance by crop plants such as, for example, cotton, wheat and sugar beet is shown, for example, by the compounds of Preparation Example l, 3, 6, 9, 10, 1 l, 17, 19, 20, 22, 34, 43, 53, 54, 55 and 59.

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Le A 32 998-Foreign Countries Lu/wa/NT

Example C
Podosphaera test (apples) / protective Solvent: 47 parts by weight of acetone Emulsifier: 3 parts by weight of alkylaryl polyglycol ether To prepare a suitable active compound preparation, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the apple mildew pathogen Podosphaera leucotricha. The plants are then placed in the greenhouse at approx. 23°C
and a relative atmospheric humidity of approx. 70%.
10 days after the inoculation, the test is evaluated. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no infection is observed.
In this test, an efficacy of 85% to 100% is shown, for example, by the compounds of Preparation Example 3, 24, 26, 29 and 30 at an application rate of in each case 100 g/ha.

Le A 32 998-Foreign Countries TABLE C
Podosphaera test (apples) / protective Active compound Application rate of Efficacy active compound in in g/ha COO
SOZ O
//O
N
N ~ NCH

(3) 100 97 F F
F
SOZ
H-CO O
N
N ~ N

(24) 100 99 Le A 32 998-Foreign Countries T A B L E C
(continued) Podosphaera test (apples) / protective Active compound Application rate of Efficacy active compound in in g/ha ~--CHa CO O

N-CO O
H
N
N ~ N

(26) 100 97 ~CH3 O
SOZ
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H
N
N ~ N

(29) 100 89 Le A 32 998-Foreign Countries T A B L E C
(continued) Podosphaera test (apples) / protective Active compound Application rate of Efficacy active compound in in g/ha Br N-CO O
H
N
N ~ N
~/

(30) 100 85 Le A 32 998-Foreign Countries Example D
Pyricularia test (rice) / systemic Solvent: 2.5 parts by weight of acetone Emulsifier: 0.06 part by weight of alkylaryl polyglycol ether#
To prepare a suitable active compound preparation, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration.
To test for systemic properties, 40 ml of the active compound preparation are poured onto standard soil in which young rice plants were grown. 7 days after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants then remain in a greenhouse at a temperature of 25°C and a relative atmospheric humidity of 100% until the test is evaluated.
4 days after the inoculation, the test is evaluated. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no infection is observed.
In this test, an efficacy of between 70% and 100% is observed, for example, by the compounds of Preparation Example 1, 2, 3, 4, 9, 10, 11, 13, 14, 18, 21, 22, 26 and 34 at an application rate of in each case 2 mg/100 cm2.

Le A 32 998-Foreign Countries TABLE D
Pyricularia test (rice) / systemic Active compound Application rate of Efficacy active compound in ~/o in mg/100 cm' COO

~~O
N
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) 2 100 F
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~~O
N
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~l~ 2 100 Le A 32 998-Foreign Countries TABLE D
(continued) Pyricutaria test (rice) / systemic Active compound Application rate of Efficacy active compound in in mg/100 cm2 F F
F

//O
N
\/
N ~ NCH

(4) 2 100 ~CH3 O
SOz O
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N
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N ~ NCH

(9) 2 I 00 Le A 32 998-Foreign Countries TABLE D
(continued) Pyricularia test (rice) / systemic Active compound Application rate of Efficacy active compound in in mg/100 cm2 Br SOz O
//O
N
\/
N ~ N~'CH

(10) 2 100 ~~O
N
~/
N ~ NCH

(11) 2 100 Le A 32 998-Foreign Countries TABLE D
(continued) Pyricularia test (rice) / systemic Active compound Application rate of Efficacy active compound in in mg/ 100 cm' CI

O
N
\/
N ~ N1CH

(13) 2 90 SOZ O
//O
N
'/
N ~ NCH

(14) 2 100 Le A 32 998-Foreign Countries TABLE D
(continued) Pyricularia test (rice) / systemic Active compound Application rate of Efficacy active compound in in mg/100 cm' i Hs O
i -CH3 N-~ //O

N ~ NCH

( 18) 2 70 H3C~ ,CH3 N
SOZ NCO
N
N\ NCO
N

SOz H
.N
(2) 2 100 Le A 32 998-Foreign Countries TABLE D
(continued) Pyricularia test (rice) / systemic Active compound Application rate of Efficacy active compound in in mg/ I 00 cm' ~N
N~ O
H O
N-~ //O

N ~ NCH

(21 ) 2 80 O
SOZ
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H
N
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V/

(22) 2 100 Le A 32 998-Foreign Countries TABLE D
(continued) Pyricularia test (rice) / systemic Active compound Application rate of Efficacy active compound in in mg/ 100 cm'-COO
SOZ
N-CO O
H
N
N ~ N

(26) 2 80 N-CO O
H
N
N ~ N

(34) 2 90 Le A 32 998-Foreicn Countries Example E
Pyricularia test (rice) / induction of resistance Solvent: 2.5 parts by weight of acetone Emulsifier: 0.06 part by weight of alkylaryl polyglycol ether To prepare a suitable active compound preparation, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration.
To test for resistance-inducing activity, young rice plants are sprayed with the active compound preparation at the stated application rate. Five days after the treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae.
The plants are subsequently placed in a greenhouse at a relative atmospheric humidity of 100% and a temperature of 25°C.
4 days after the inoculation, the test is evaluated. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no infection is observed.
In this test, an efficacy of between 80% and 100% is shown, for example, by the compounds of Preparation Example l, 2, 3, 4, 9, 10, 11, 13, 14, 18, 21, 22, 26 and 34 at an application rate of in each case 375 g/ha.

Le A 32 998-Foreign Countries TABLE E
Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha CO-O

//O
N
N ~ NCH

(3) 375 100 F
O
F

~~O
N
~/
N ~ NCH

(1) 375 100 Le A 32 998-Foreicn Countries TABLE E
(continued) Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha F F
F
SOZ O
//O
N
\/
N ~ NCH

(4) 375 90 ~CH3 O

O
N
\/
N ~ N~CH3 (9) 375 100 Le A 32 998-Foreign Countries TABLE E
(continued) Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha Br SOZ O
//O
N
'/
N ~ NCH

(10) 375 80 SOZ O
//O
N
\/
N ~ NCH

(11) 375 90 Le A 32 998-Foreign Countries TABLE E
(continued) Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha CI

//O
N
N ~ NCH

(13) 375 90 SOZ O
~~O
N--5' ~/
N ~ NCH

(14) 375 80 Le A 32 998-Foreicn Countries TABLE E
(continued) Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha i Hs O

SOz H O
N~ O

N ~ ~N~CH

(18) 375 100 H3C~ ,CH3 N

N-CO

N ~ NCH

(?) 375 100 Le A 32 998-Foreign Countries TABLE E
(continued) Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha ~N
N~ I
OH O
O

N ~ ,NCH

(2 I ) 375 100 -O
SOZ
N---CO O
H
N
N ~ N

(22) 375 90 Le A 32 998-Foreign Countries TABLE E
(continued) Pyricularia test (rice) / induction of resistance Active compound Application rate of Efficacy active compound in in g/ha CO-O
SOZ
N-CO O
H
N
N ~ N

(26) 375 100 SOZ
N-CO O
H
N
N ~ N

(34) 375 l00

Claims (9)

Claims

1. Compounds of the general formula (I) in which Q1 represents oxygen or sulphur, Q2 represents oxygen or sulphur, R1 represents hydrogen, amino, alkylideneamino, or a radical from the series alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, in each case optionally substituted, R2 represents optionally substituted alkenyl and R3 represents a radical from the series alkyl, aralkyl, aryl and heteroaryl, in each case optionally substituted, and salts of compounds of the formula (I).

2. Compounds of the formula (I) according to Claim 1, characterized in that, in this formula, R1 represents hydrogen, amino, C1-C6-alkylideneamino, or represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl, or represents C2-C6-alkenyl or C2-C6-alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C1-C6-alkyloxy or C2-C6-alkenyloxy, or represents C1-C6-alkylamino, di-(C1-C4-alkyl)-amino or C1-C4-alkyl-carbonyl-amino, each of which is optionally substituted by fluorine and/or chlorine, or represents C3-C6-cycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine and/or C1-C4-alkyl, or represents phenyl or phenyl-C1-C4-alkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy and/or C1-C4-alkoxy-carbonyl, R2 represents C2-C6-alkenyl which is optionally substituted by cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl, R3 represents the group where R4 and R5 are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C1-C6-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C1-C4-alkoxycarbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, C1-C4-alkoxy, 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)-amino-sulphonyl, C3-C6-cycloalkyl or phenyl), or represents C2-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl or phenyl), or represents C2-C6-alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl or phenyl), or represents C1-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl or C3-C6-cycloalkyl), or represents C1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represents C2-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represents C2-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C3-alkylthio or C1-C4-alkoxy-carbonyl), or represents C3-C6-alkinyloxy, C3-C6-alkinylthio or 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 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-alkylsulphinyl, C1-C4-alkylsulphonyl, C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl or di-(C1-C4-alkyl)-amino-carbonyl), or represents C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), or represents 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), or represents diphenylmethyl, 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, or 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-alkyl-amino or di-(C1-C4-alkyl)-amino (which are optionally substituted by fluorine and/or chlorine), R4 and/or R5 furthermore represent trimethylsilyl, thiazolinyl, 1,2,4-oxa-diazol-5-yl, 3-methyl-1,2,4-oxadiazol-5-yl, 1,3-dioxolan-2-yl, C1-C4-alkylsulphonyloxy, di-(C1-C4-alkyl)-aminosulphonylamino or represent the radical -CH=N-R9 where R9 represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C3-C6-alkenyl or C3-C6-alkinyl which are optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or benzyloxy, which are optionally substituted by fluorine and/or chlorine, or represents amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C1-C4-alkyl-carbonylamino, C1-C4-alkoxy-carbonylamino, C1-C4-alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl;
R3 furthermore represents the radical where R10 represents hydrogen or C1-C4-alkyl, R11 and R12 are identical or different and 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), carboxyl, C1-C4-alkoxy-carbonyl, dimethylamino-carbonyl, C1-C4-alkylsulphonyl or di-(C1-C4-alkyl)-amino-sulphonyl;
R3 furthermore represents the radical where R13 and R14 are identical or different and 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);
R3 furthermore represents the radica where R15 and R16 are identical or different and 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), or represent C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(C1-C4-alkyl)-aminosulphonyl, or represent di-(C1-C4-alkyl)-aminosulphonyl or C1-C4-alkoxy-carbonyl or dimethylamino-carbonyl;
R3 furthermore represents the radical where R17 and R18 are identical or different and 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), or represents C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C1-C4-alkyl)-amino-sulphonyl;
R3 furthermore represents the radical where R19 and R20 are identical or different and 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-alkylsulphinyl or C1-C4-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), di-(C1-C4-alkyl)-amino-sulphonyl, C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl, and A represents oxygen, sulphur or the group N-T where T 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-alkylcarbonyl, C1-C4-alkoxy-carbonyl or di-(C1-C4-alkyl)-aminocarbonyl;
R3 furthermore represents the radical where R21 and R22 are identical or different and represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy or C1-C4-halogenoalkoxy, Y1 represents sulphur or the group N-R23 where R23 represents hydrogen or C1-C4-alkyl;
R3 furthermore represents the radical where 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 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 and di-(C1-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I).

3. Compounds of the formula (I) according to Claim 1 or 2, characterized in that, in this formula, R1 represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, or represents propenyl, butenyl, propinyl or butinyl, each of which is optionally substituted by fluorine, chlorine or bromine, or represents methoxy, ethoxy, n- or i-propoxy, or represents allyloxy, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or represents cyclopropyl which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, R2 represents ethenyl, propenyl or butenyl, each of which is optionally substituted by cyano, fluorine, chlorine and/or bromine, and R3 represents the radical where R4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-fluoro-ethoxy, 2,2-difluoro-ethoxy, 2,2,2-trifluoro-ethoxy, 1,1,2,2-tetrafluoro-ethoxy, 1,1,2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, cyclopropylmethoxy, methylthio, ethylthio, n- or i-propylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethyl-sulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl and R5 represents hydrogen, fluorine, chlorine, bromine methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro-methoxy, trifluoromethoxy, methylthio or ethylthio;
R3 furthermore represents the radical where R10 represents hydrogen, R11 represents fluorine, chlorine, bromine, methyl, methoxy, di-fluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl R12 represents hydrogen;
R3 furthermore represents the radical where R represents methyl, ethyl, n- or i-propyl, or R3 represents the radical where R24 represents methyl, ethyl, n- or i-propyl, phenyl or pyridyl, R25 represents hydrogen, fluorine, chlorine or bromine, and R26 represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.

4. Process for the preparation of compounds of the formula (I) according to one of Claims 1-3, characterized in that (a) triazolin(ethi)ones of the general formula (II) in which Q1, R1 and R2 have the meanings given in any of Claims 1-3 are reacted with sulphonyliso(thio)cyanates of the general formula (III) R3-SO2-N=C=Q2 (III) in which Q2 and R3 have the meanings given in any of Claims 1-3, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or in that (b) triazolin(ethi)one derivatives of the general formula (IV) in which Q1 Q2 R1 and R2 have the abovementioned meanings and Z represents halogen, alkoxy, aralkoxy or aryloxy are reacted with sulphonamides of the general formula (V) R3-SO2-NH2 (V) in which R3 has the abovementioned meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or in that (c) triazolin(ethi)ones of the general formula (II) in which Q1, R1 and R2 have the abovementioned meanings are reacted with sulphonamide derivatives of the general formula (VI) R3-SO2-NH-CQ2-Z (VI) in which Q2 and R3 have the abovementioned meanings 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 in that (d) triazolin(ethi)ones of the general formula (II) in which Q1, R1 and R2 have the abovementioned meanings are reacted with sulphonyl halides of the general formula (VII) R3-SO2-X (VII) in which R3 is as defined above and X represents halogen and with metal (thio)cyanates of the general formula (VIII) MQ2CN (VIII) in which Q2 is as defined above and M represents an alkali metal or alkaline earth metal equivalent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and, if appropriate, the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are converted into salts by customary methods.

5. Herbicidal and fungicidal compositions, characterized in that they contain at least one compound of the formula (I) according to one of Claims 1-3.

6. Use of compounds of the general formula (I) according to one of Claims 1-3 for controlling undesired plant growth and/or phytopathogenic fungi.

7. Method of controlling weeds and/or phytopathogenic fungi, characterized in that compounds of the general formula (I) according to one of Claims 1-3 are allowed to act on the weeds or fungi, or their environment.

8. Process for the preparation of herbicidal or fungicidal compositions, characterized in that compounds of the general formula (I) according to one of Claims 1 to 3 are mixed with extenders and/or surfactants.

9. Compounds of the general formula (XIV) in which R1, R2 and Q1 have the meanings given in one of Claims 1-3 and A represents hydrogen or the group -CQ2-Z where Q2 has the meaning given in Claim 1 and Z represents halogen, alkoxy, aralkoxy or aryloxy.