CA2214752C - Herbicidal or fungicidal sulphonylaminocarbonyltriazolinones with halogenated alk(en)oxy substituents - Google Patents

Abstract

The invention relates to novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the formula (I) (see formula I) in which R1 represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, R2 represents respectively halogen-substituted alkyl or alkenyl, 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), and to processes and novel intermediates for preparing the compounds (I), and to their use as herbicides and/or fungicides.

Description

. .

Le A 30 930-Foreign countries / ~ Bi/Kr/ S-P~IbI

~ulnhonXlaminocarbonyltuiazolnnones having ha ~enoalkoxv swbstituents The invention relates to navel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents, to a plurality of processes and to novel intermediates for their preparation and to their use as herbicides and fungicides.
Certain sulphonylaminocarbonyltriazolinones are known to have herbicidal properties (cf. EP-A 34148, EP-A 422469, EP-A 425948, EP-A 431291, EP-A
507171). However, the activity of these compounds is not in all aspects satisfactory.
This invention, then, provides sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the general formula (I) o o R' S02_N ~~ N (I) N =-C

in which R' represents hydrogen, hydroxyl, amino, alkylideneamino or a respectively optionally substituted radical from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylamino, dialkylamino, alkanoylamino, cycloalkyl, cycloalkylalkyl, cycloalkylamino, aryl and arylalkyl, Ra represents respectively halogen-substituted~alkyl or alkenyl, and R3 represents a respectively optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, t h w:' T_.e A 30 930-Foreign countrie~

and salts of the compounds of the formula (I).
The novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents of the general formula (I) are obtained when (a) triazolinones of the general formula (II) H~N~N~R~
(II) N=
O-RZ
in which R' and R2 are each as defined above are reacted with sulphonyl isocyanates of the general formula (III) R3-S02-N=C=O (III) ' in which R3 is as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or (b) triazolinone derivatives of the general formula (I~

~,e A 30 930-Foreign countries o O
R' - ~N~N~
Z
N (IV) in which R1 and R2 are each as defined above, and Z represents halogen, alkoxy, aralkoxy or aryloxy, are reacted with sulphonamides of the general formula (V) R3-S~z-NH2 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) triazolinones of the general formula (II) O
H~N~N~R' N (II) O-RZ
in which rl Le A 30 930-Foreign countries R' and R2 are each as defined above are reacted with sulphonamide derivatives of the general formula (VI) R3-S02-NH-CO-Z (VI) in which S R3 is 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) triazolinones of the general formula (II) O
H~N~N~R' v (II) N
O-RZ
in which R' and R2 are each as defined above are reacted with sulphonyl halides of the general formula (VII) R3- SO2- X (VI I ) T a A 30 930-F'oreiQn countries in which R3 is as defined above and X represents halogen and metal cyanates of the general formula (VIII) MOCN (VIII) in which M represents an alkali metal equivalent 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, if appropriate, the compounds of the formula (I) obtained by process (a), (b), (c) or (d) are converted by customary methods into salts.
The novel sulphonylaminocarbonyltriazolinones having halogenoalkoxy substituents ofthe general formula (I) have a strong herbicidal and/or fungicidal activity.
The invention preferably provides compounds of the formula (I) in which Ri represents hydrogen, hydroxyl, amino, C1-C6-alkylideneamino, optionally fluorine-, chlorine-, bromine-, cyano-, CI-C4-alkoxy-, CI-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted CI-C6-alkyl, respectively, optionally fluorine-, chlorine- and/ or bromine-substituted T.e A 30 930-Foreign: countries C2-C6-alkenyl or C2-C6-alkynyl, respectively optionally fluorine- and/or chlorine-substituted C1-C6-alkoxy or C2-C6-alkenyloxy, respectively optionally fluorine- and/or chlorine-substituted CI-C6-alkylamino, di-(C 1-C4-alkyl)-amino or C,-C4-alkanoylamino, respectively optionally fluorine-, chlorine-, bromine- and/or CI-C4-alkyl-substituted C3 C6-cycloalkyl or C3-C6-cycloalkyl-CI-C4-alkyl, or respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, Cl-C4-alkyl-, trifluoromethyl-, CI-C4-alkoxy- and/or C1-C4-alkoxy-carbonyl-substituted phenyl or phenyl-C1-C4-alkyl, R2 represents respectively fluorine-, chlorine- and/or bromine-substituted C,-C6-alkyl or C2-C6-alkenyl, and _ R5 R3 . represents the grouping \ /

in which R4 and RS 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, carboxyl, C,-C4-alkoxycarbonyl, CI-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, hydroxyl, CI-C4-alkoxy, formyloxy, C I-C4 alkyl-carbonyloxy, C,-C4-alkoxy-carbonyloxy, C 1-C4 alkylamino-carbonyloxy, C 1-C4-alkylthio, C 1-C4-alkylsulphinyl, Ci-C4-alkylsulphonyl, di-(C1-C4-alkyl)-aminosulphonyl, C3-C6-cycloalkyl or phenyl), or C2-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, CI-C4 alkoxy-_ 7-carbonyl, carboxyl or phenyl), or CZ-C6-allc5myl (which is optionally substituted by fluorine, chlorine, bromine, cyano,_ C1-C4-alkoxy-carbonyl, carboxyl or phenyl), or C1-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C,-C4-alkoxy-carbonyl, CI-C4-alkoxy, C1-C4-alkylthio, CI-C4-alkylsulphinyl or C,-C4-alkylsulphonyl), or C 1-C4-alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C,-C4-alkoxy-carbonyl, C1-C4-alkylthio, CI-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or C2-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or CI-C4-alkoxy-carbonyl), or C2-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, vitro, C1-C3-alkylthio or C,-C4-alkoxycarbonyl), C3-C6-alkynyloxy, C3-C6-alkynylthio 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 CI-C4-alkoxy-carbonyl), C3-C6-alkenyl, C3-C6-alkynyl, C,-C4-alkoxy, Cl-C4-alkoxy-C,-C4-alkylamino, CI-C4-alkylamino, di-(CI-C4-alkyl)-amino, phenyl or the radical -NHOR', where R' represents C t-C 1z-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C 1-C4-alkoxy, C 1-C4-alkylthio, C 1-CQ-alkylsulphinyl, C1-C4-alkylsulphonyl, C,-C4-alkyl-carbonyl, C~-C4-alkoxy-carbonyl, C,-C4-alkylamino-carbonyl or di-(C,-C4-alkyl)-amino-carbonyl), or C3-C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alk5myl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl, phenyl-Ci-C2-alkyl (which is optionally substituted by fluorine, chlorine, vitro, cyano, C i-C4-alkyl, CI-C4-alkoxy or C1-C4-alkoxy-carbonyl), or benzhydryl or - $-phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, CI-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C,-C2-fluoroalkoxy, CI-C4 alkylthio, trifluoromethylthio or C1-C4-alkoxy-carbonyl), R4 and/or RS further represent phenyl or phenoxy, or C,-C4-alkyl-carbonylamino, CI-C4-alkoxy-carbonylamino, CI-C4-alkylamino-carbonyl-amino, di-(C1-C4-alkyl)-amino-carbonylamino, or the radical -CO-R8, where R8 represents hydrogen, C,-C6-alkyl, C3-C6-cycloalkyl, C,-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C~-C4-alkylthio, C,-C4 alkylamino, C1-C4-alkoxyamino, C,-C4-alkoxy-CI-C4-allcylamino or di-(C1-C4-alkyl)-amino (each of which is optionally substituted by fluorine and/ or chlorine), R4 and/or RS further represent trimethylsilyl, thiazolinyl, CI-C4-alkyl-sulphonyloxy, di-(C1-C4-alkyl)-aminosulphonylamino or the radical -CH=N-R9, where R9 represents optionally fluorine-, chlorine-, cyano-, carboxyl-, C,-C4-alkoxy-, C1-C~-allcylthio-, C,-C4-alkylsulphinyl- or C,-C4 alkylsulphonyl-substituted C I-C6-alkyl, or optionally fluorine- or chlorine-substituted benzyl, or optionally fluorine- or chlorine-substituted C3-C6-alkenyl or C3-C6-alkynyl, or optionally fluorine-, chlorine-, bromine-, C I-C4-alkyl-, C,-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, or optionally fluorine- and/or chlorine-substituted CI-C6-alkoxy, C3-C6-alkenoxy, C3-C6-alkinoxy or benzyloxy, or amino, C I-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C,-C4-alkyl-carbonyl-amino, C1-C4-alkoxy-carbonylamino, C1-C4-alkyl-sulphonylamino or optionally fluorine-, chlorine-, bromine- or methyl-substituted phenylsulphonylamino, furthermore - Rio - R~2 R3 represents the radical -CH ~
R' 1 in which R'° represents hydrogen or C,-C4-alkyl, R" and R'2 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, CI-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/ or chlorine), carboxyl, C I-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C1-C4 alkyl-sulphonyl or di-(C I-C4-alkyl)-aminosulphonyl;
furthermore R3 represents the radical R~3 ~ ~ ~ Rya in which 1~ -R'3 and R'4 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) or C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine);
furthermore R, s R3 represents the radical in which R'S and R'6 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), Ci-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or C1-C4-alkylthio, C,-C4-alkylsulphinyl or CI-C4-alkylsulphonyl (each of which are optionally substituted by fluorine and/or chlorine), or aminosulphonyl, mono-(CI-C4-alkyl)-aminosulphonyl, or di-(Cl-C4-alkyl)-amino-sulphonyl or CI-C4-alkoxy-carbonyl or dimethylaminocarbonyl;
furthermore R3 represents the radical R" ~ ~ ~ R'$
-N

in which R" and R'8 are identical or different and each represent hydrogen, fluorine, chlorine, bromine, C,-C4-alkyl (which is optionally substituted by fluorine and/or bromine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl (each of which are optionally substituted by fluorine and/or chlorine), or di-(C1-C4-alkyl)-aminosulphonyl;
furthermore R, s R3 represents the radical ~ I R2o A
in which R'9 and R2° are identical or different and each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, CI-C4 alkyl (which is optionally substituted by fluorine and/or chlorine), CI-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), CI-C4-alkylthio, C1-C4-alkylsulphinyl or CI-C4-alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C1-C4 alkyl)-amino-sulphonyl, CI-C4-alkoxy-carbonyl or dimethylamiglocarbonyl, and A represents oxygen, sulphur or the grouping N-Z', where Z' represents hydrogen, C 1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C3-C6-cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C,-C4-alkylcarbonyl, C1-C4-alkoxy-carbonyl or di-(CI-C4-alkyl)-aminocarbonyl; .
furthermore R2' R3 represents the radical ~ ~ R22 Y' in which R21 and R~ are identical or different and each represent hydrogen, C1-C4-alkyl, halogen, CI-C4-alkoxycarbonyl, C,-C4-alkoxy or C,-C4-halogenoalkoxy, Y' represents sulphur or the grouping N-R'~, where R'~ represents hydrogen or CI-C4-alkyl;
furthermore Rzs R2s R3 represents the radical N~
~N

in which R24 represents hydrogen, C,-C4-alkyl, benzyl, pyridyl, quinolyl or phenyl, ' ' . CA 02214752 1997-09-OS

R~ represents hydrogen, halogen, cyano, vitro, C,-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 C I-C4-alkoxy-carbonyl, and S R26 represents hydrogen, halogen or C1-C4-alkyl, Additionally, the invention preferably provides the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di-(Cl-C4 alkyl)-ammonium, tri-(C,-C4-alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, CS- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which n, R1, R2 and R3 have the preferred meanings given above.
The invention in particular provides compounds of the formula (I) in which R' represents respectively optionally fluorine-, chlorine-, cyano-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propynyl or butynyl, or represents respectively optionally fluorine- and/or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy or butenyloxy, or represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, or 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 represents fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-v i.e A 30 930-Foreign countr;P~

propyl, n-, i-, s- or t-butyl, and R3 represents the radical \ /

in which R4 represents fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and RS' represents hydrogen, methyl, ethyl, fluorine, chlorine or bromine;
furthermore R"
_ R' 2 R3 represents the radical -CH
\ /
Rio in which - T:e A 30 930-Foreign countries R'° represents hydrogen, R'I represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl, and R12 represents hydrogen;
furthermore R3 represents the radical RO-C S
'J
O
in which R represents methyl, ethyl, n- or i-propyl, or RZS R2s R3 represents the radical ~ ~N
N

in which 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.
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 preparation. These radical definitions can be combined with one another as desired, thus including combination between the preferred ranges indicated.
In the definitions of the radicals, hydrocarbon radicals such as alkyl, alkenyl or alkynyl are straight-chain or branched, even in combination with hetero atoms, as in alkoxy, alkylthio or alkylamino, even if this is not explicitly stated .
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Using, for example, 2-trifluoromethoxy-phenylsulphonyl isocyanate and 4-ethyl-5-difluoromethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following equation:

O-CFa ~ ~ O O
+ w H~N N~CzI-Is ~ SOz' C~,N~N~C2H5 SOZ N=C=O N NH
N
~O-CHFz O-CHF
z Using, for example, 2-ethylthio-benzenesulphonamide and 2-chlorocarbonyl-4-benzyl-5-(2,2-difluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation:

CA 02214752 1997-09-OS .

O O / S-CzHs / S-CzHs ~ I O O
I + .N N~CI-Iz CsHs W
CI ~ -i SOz.N~N~N~CH2 CsHS
w SOZ NHz N=~ - HCI
O-CH2CHFz N
O-CHaCHFz Using, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-(2-chloro-ethoxy)-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one as~ starting materials, the course of the reaction of the process (c) according to the invention can be illustrated by the following equation:

O CH3 + ~ \ I O O
H~N N~CH3 ~ SO ~ ~ ~CH3 I ~ _ -HOCH z~NH N N
SOz NH-COOCH3 N~ 3 N=--C
O-CH2CHzCi O-CH2CH2CI
Using, for example, 2-chloro-6-methyl-benzenesulphonyl chloride, 4-allyl-5-(2,3,3-trifluoro-propoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one and sodium cyanate as starting materials, the course of the reaction of the process (d) according to the invention can be illustrated by the following equation:

+H~N~N~CH2 CH=CHz ~ I O O
S02 CI ~ ~ + NaOCN SO ~ N ~ N ~ CHz CH=CHz N ~ z NH
CI O-CHZCHFCHFz - NaCI CI N
O-CHzCHFCHFz A general definition of the triazolinones to be used as starting materials in the processes (a), (c) and (d) according to the invention for preparing compounds of the formula (I) is given by the formula (II).
In the formula (II), R' and R2 each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for R1 and RZ.
The triazolinones of the general formula (II) have not been disclosed in the literature; as novel substances, they also form part of the subject matter of the present application.
The novel triazolinones of the formula (II) are obtained when carbazates of the general formula (I~
O
NH~ O OX) I I
NHz R
in which R represents alkyl (preferably methyl or ethyl) are reacted with diesters of alkyliminocarbonic acid of the general formula (X~
R' N
z ~ z ~X) R~O O~R
in which R' and R2 are as defined above, if appropriate in the presence of a diluent such as methanol at temperatures between 0°C and 100°C and the thus-formed compounds ofthe general formula ( CA 02214752 1997-09-OS .

O
H.N~O.R _ I (XI) N~NHR~ .
IO~R2 in which R, R' and R2 are as defined above are cyclocondensed - if appropriate after intermediate isolation - if appropriate in the presence of a diluent such as toluene at temperatures between 20°C and 150°C (cf. the preparation examples).
The triazolinones of the formula (II) in which RZ represents difluoromethyl (R' being as defined above) are preferably prepared by reacting urazoles of the general formula (~I) O
R, H~N~N' (XII) ~N
H O
in which R' is as defined above with chlorodifluoromethane in the presence of an acid acceptor such as sodium hydroxide and in the presence of a diluent such as isopropanol aiZd/or water, at IS temperatures between 0°C and 100°C (cf. the preparation examples).
A'general definition of the sulphonyl isocyanates also to be used as starting CA 02214752 1997-09-OS .

materials in the process (a) according to the invention for preparing compounds of the formula (I) is given by the formula (III).
In the fprmula (III), R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferable or particularly preferable for R3.
The starting materials of the formula (III) are known and/or can be prepared by methods knovv~l 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 triazolinone derivatives to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (I~. In the formula (I~, R' and R2 each preferably or in particular have that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R' and R2;
Z
preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogeno- or nitro-phenoxy, and in particular represents methoxy, phenoxy or 4-nitro-phenoxy.
The starting materials of the formula (I~ have not been disclosed in the literature; as novel substances, they are also part of the subject matter of the present application.
The novel compounds of the formula (I~ are obtained when triazolinones of the general formula (II) O
H~N~N~R' _ N _ (I I) v~
O-Rz in which R' and R2 are each as defined above, are reacted with carbonic acid derivatives of the general formula (XIII) Z-CO-Z' (XIII) in which Z is as defined above and Z' represents halogen, alkoxy, aralkoxy or aryloxy, if appropriate in the presence of an acid acceptor, such as, for example, potassium t-butoxide, and if appropriate in the presence of a diluent, such as, for example, tetrahydrofuran or dimethoxyethane, at temperatures between 0°C
and 100°C.
A general definition of the sulphonamides also to be used as starting materials in the process (b) according to the invention for preparing compounds of the general formula (I) is given by the formula (~. In the formula (~, R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R3.
The starting materials of the formula (~ are known andl 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 S 1466, EP-A
64322, EP-A 70041, EP-A 173312).
A general definition of the sulphonamide derivatives to be used as starting materials in the process (c) according to the invention for preparing compounds of the formula (I) is given by the formula (VI). In the formula (VI), R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R3; Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, and in particular represents methoxy or phenoxy.
The starting materials of the formula (VI) are known and/ or. can be prepared by methods known per se.
A general definition of the sulphonyl halides to be used as starting materials in the process (d) according to the invention for preparing compounds of the formula (I) is given by the formula (VII). In the formula (VII), R3 preferably or in particular has that meaning which has already been indicated above, in connection with the description of the compounds of the formula (I), as being preferable or particularly preferable for R3; X preferably represents fluorine, chlorine or bromine, and in particular represents chlorine.
The starting materials of the formula (VII) are known and/or can be prepared by methods known per se.
The processes (a), (b), (c) and (d) according to the invention for the preparation of the novel compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context are virtually all inert organic solvents. These include, preferably, aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene; ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane;
ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone; esters such as methyl acetate and ethyl acetate;
nitrites, for example acetonitrile and propionitrile; amides, for example dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.
As reaction auxiliaries and/ or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention it is possible to employ all acid-binding agents which can customarily be used for such reactions. Preference is given to alkali metal hydroxides, for example sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, for example calcium hydroxide, alkali metal carbonates and alkoxides, such as sodium carbonate and potassium carbonate, sodium tent-butoxide and potassium tert-butoxide, and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, 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-S
ene (DBN), 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU) and 1,4-diazabicyclo [2,2,2]-octane (DABCO).
The reaction temperatures in the processes (a), (b), (c) and (d) according to the invention can be varied within a relatively wide range. The reactions are in general carried out at temperatures of between -20°C and +
100°C, preferably at temperatures between 0°C and +80°C.

The processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure.
For carrying out processes (a), (b), (c) and (d) according to the invention, the starting materials required in each case are in general employed in approximately equimolar quantities. However, it is also possible to use one of the components employed in each case in a relatively large excess. The reactions are in general carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for a number of hours at the particular temperature required. Work-up in the case of the processes (a), (b), (c) and (d) according to the invention is in each case carried out by customary methods (cf. the Preparation Examples).
Salts of the compounds of the general formula (I) according to the invention ., can be prepared if desired. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in an appropriate solvent, for example methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding an appropriate base. The salts can then - if desired after prolonged stirring - be isolated by concentration or filtration with suction.
The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are not wanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotvledonous weeds of the nera~ Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
j Dicotyledonous crops of the nge era:era: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vcia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and 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 and Apera.
Monocotyledonous crops of the ~en,_ era: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the. active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial crops, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pasture-land, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention are preferably suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both pre-emergence and post-emergence.
Additionally, the active compounds according to the invention have a potent microbicidal action and can be practically employed for controlling undesirable microorganisms. The active compounds are suitable for use as crop protection agents, in particular as fungicides.
Fungicides in plant protection are employed for controlling Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bactericides in plant protection are employed for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Some causative organisms of fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as Xanthomonas campestris pv. oryzae;
Pseudomonas species, such as Pseudomonas syringae pv. lachrymans;
Erwinia species, such as Erwinia amylovora;
Pythium species, such as Pythium ultimum;
Phytophthora species, such as Phytophthora infestans;
Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as Plasmopara viticola;
Bremia species, such as Bremia lactucae; t Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;
Sphaerotheca species, such as Sphaerotheca fuliginea;
Podosphaera species, such as Podosphaera leucotricha;
Venturia species, such as Venturia inaequalis;
Pyrenophora species, such as Pyrenophora teres or P. graminea (conidia form: Drechslera, syn: Helminthosporium);
Cochliobolus species, such as Cochliobolus sativus (conidia form: Drechslera, syn: Helminthosporium);
Uromyces species, such as Uromyces appendiculatus;
Puccinia species, such as Puccinia recondita;
Sclerotinia species, such as Sclerotinia sclerotiorum;
Tilletia species, such as Tilletia caries;
Ustilago species, such as Ustilago nuda or Ustilago avenae;
Pellicularia species, such-as Pellicularia-sasakii; -Pyricularia species, such as Pyricularia oryzae;
Fusarium species, such as Fusarium culmorum;
Botrytis species, such as Botrytis cinerea;
Septoria species, such as Septoria nodorum;
Leptosphaeria species, such as Leptosphaeria nodorum;
Cercospora species, such as Cercospora canescens;
Alternaria species, such as Alternaria brassicae;
Pseudocercosporella species, such as Pseudocercosporella herpotrichoides.
The good toleration, by plants, of the active compounds, at the concentrations required for controlling plant diseases, permits treatment of aerial parts of plants, of vegetative propagation stock and seeds, and of the soil.
The compounds of the formula (I) are particularly suitable for the protective treatment of pomaceous fruit, such as apples, against the causative organism of powdery mildew in apple (Podosphaera leucotricha) and to a certain extent also for use in rice against Pyricularia oryzae.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
For example, a herbicidal or fungicidal composition comprising a herbicidally or fungicidally effective amount of a compound of the invention in admixture with a solid diluent or carrier, a liquefied normally gaseous diluent or carrier, or a liquid diluent or carrier containing a surface active agent.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. Suitable liquid solvents are in the main:
aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

- 28a -Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifying and/or foam-forming agents are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, allcylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates; suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, ready-to-use formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, for example anilides, such as diflufenican and propanil; arylcarboxylic acids, such as dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids, such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters, such as diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones, such as chloridazon and norflurazon; carbamates, such as chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides, such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor;

dinitroanilines, such as oryzalin, pendimethalin and trifluralin; diphenyl ethers, _ such as aciffuorfen, bifenox, ffuoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; areas, such as chlorotoluron, diuron, fluometuron, isproturon, linuron and methabenzthiazuron; hydroxylamines, such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones, such as imazethapyr, imazamethabenz, imazapyr and imazaquin; nitrites, such as bromoxynil, dichlobenil and jioxynil; oxyacetamides, such as mefenacet;
sulphonyl-areas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates, such as butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, such as atrazine, cyanazine, simazine, simetryne, terbutryne and terbutylazine;
triazinones, such as hexazinone, metamitron and metribuzin; others, such as 1 S aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, defenzoquat, dithiopyr, ethofumesate, ffuorochloridone, 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.
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 scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 2 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the examples below.

I~e A 30 930-Foreign countries Preparation Exam~s_ Exam in a 1 O

SOZ, ~N~N
NH ~
N

(Process (a)) A solution of 1.9 g (9.5 mmol) of 4-methyl-S-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one in 50 ml of acetonitrile is mixed with 2.4 g (10 mmol) of 2-methoxycarbonyl-phenylsulphonyl isocyanate, and the mixture is stirred at 20°C for 12 hours. The mixture is then concentrated under reduced pressure and the residue is crystallized from diethyl ether.
3.7 g (89% of theory) of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 153°C are obtained.

H3C ~OCH3 N
I

O
SOZ_ ~N~N~CH3 NH ~
N

(Process (b)) 3.8 g(12 mmol)of4-methyl-2-phenoxycarbonyl-5-(2,2,2-trifluoroethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 20 ml of acetonitrile and admixed with 3.4 g (12 mmol) of 2-(N-methoxy-N-methyl-aminosulphonyl)-benzenesulphonamide and 1.9 g (12.5 mmol) of diazabicycloundecene (DBU).
After the mixture has been stirred at 20°C for 1 hour, it is poured into a mixture of methylene chloride/ 5% strength hydrochloric acid, and the organic phase is separated off, dried with sodium sulphate and concentrated under reduced pressure. The residue is crystallized using diethyl ether.
3.3 g (55% of theory) of 2-[2-(N-methoxy-N-methyl-aminosulphonyl)-phenylsulphonyl-aminocarbonyl~-4-methyl-5-(2,2,2-trifluoroethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 183°C are obtained.

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 example, the compounds of the formula (I) listed in Table 1 below.

R3 ,1 S02. NH N N ~ R CI) N=C
O-RZ
Table L. Examples of compounds of the formula (I) Ex. R' R2 R3 Melting No. point (°C) w OCzHs 5 CH3 CH2CF3 ~ ~ 135 6 CH3 CH2CF3 ~ ~ 159 Le A 30 930-Fore~1 countries Ex R' R2 R3 Melting No. point (°C) 7 CH3 CH2CF3 ~ ~ 178 w 8 CH3 CH2CF3 ~ ~ 144 COOCZHS

9 CH3 CH~CF3 ~ ~ 119 COOC3H~ n CH3 CH2CF3 ~ ~ 120 ., CI
11 CH3 CH2CF3 ~ I 203 Br 12 CH3 CH2CF3 ~ ~ 193 OCHFZ
13 CH3 CH~CF3 ~ ( 144 w 10 14 CH3 CH2CF3 ~ I 180 Ex Ri R2 R3 Melting No. point (C) . 15 CH3 CH2CF3 ~ ~ 162 CI
16 CH3 CH2CF3 ~ ~ 216 O-CHZ CH=CHz 17 CH3 CHZCF3 ~ ~ 102 _ COOCH3 18 , CH3 ~ CH2CC13 ~ ~ 129 19 CH3 CH2CC13 ~ I 122 20 CH3 CH2CC13 ~ ~ 153 21 CH3 CH2CC13 ~ ~ 140 COOCZHS
22 CH3 CH2CC13 ~ ~ 146 CA 02214752 1997-09-OS .

1_,e A 30 930-Forei ~r~ countries , - 37 -Ex. R' R2 R3 Melting No. point (C) COOC3H~
~

23 CH3 CH2CC13 ~ 148 ~

24 CH3 CH2CC13 ~ 145 OCZHS
~

25 CH3 CH2CC13 ( 142 Br 26 CH3 CH2CC13 ~ ~ 155 w 27 CH3 CH2CC13 ~ ~ 136 SCzHs ~

28 CH3 CH2CC13 ~ 158 C~
29 CH3 CH2CC13 ~ ~ 153 30 CH3 CH2CC13 ~ ~ 150 Le A 30 930-Foreism countries Ex. R1 R2 R3 Melting No. point (C) ~

31 CH3 CH2CC13 ~ 160 CI
32 CH3 CH2CC1~ ~ ~ 196 ~

33 CH3 CH2CC13 . ~ 182 ~

34 CH3 CHZ CFA-CHF2 ~ 120 OCHFZ
. ~

35 CH3 CH2-CF2-CHF2 ~ 116 36 CH3 CH2-CF2-CHF2 ~ ~ 163 ~

37 CH3 CH2-CF2-CHF2 ~ 154 COOCZHS
~

38 CH3 CH2-CFz CHF2 ~ 126 Le A 30 930-Fore~'mn countries Ex R' R2 R3 Melting No. point (C) COOC3H~ n ~

39 CH3 CH2-CF2-CHF2 ~ 109 ~

40 CH3 CH2-CF2-CHF2 ~ 160 OCZHS
~

41 CH3 CH2-CF2-CHF2 ~ 153 Br 42 CH3 CH2-CF2-CHF2 ~ ~ 163 ~

43 CH3 CH2-CF2-CHF~ I 150 ~

44 CH3 CH2-CF2-CHF2 ~ 159 CI
45 CH3 CH2-CF2-CHF~ ~ ~ 168 46 CH3 CH2-CF2-CHF2 ~ ~ 163 Ex R' . R2 R3 Melting No. - point (°C) 47 CH3 CHI-CF2-CHF2 s ~ 117 W

48 CH3 CH2-CF2-CHF2 ~ ~ 142 cl CI
49 CH3 CH2-CF2-CHF2 ~ ~ 154 CI

50 C2H5 CHa-CF3 ~ 96 OCHFZ
51 C2H5 CH2-CF3 ~ 117 52 C2H5 ~ CH2-CF3 ~ 108 53 C2H5 CH2-CF3 ~ 133 Le A 30 930-Foreign countries Ex. R' R2 R3 Melting No. point (C) COOCZHS
~

54 C~HS CH2-CF3 ~ 152 COOC3H~
~

55 C2H5 CHI CF3 ~ 117 ~

56 C~HS CH2-CF3 ~ 148 ~

57 C~HS CH2 CF3 ~ 108 Br 58 C2H5 CH2-CF3 ~ ~ 119 SCZHS
~

59 C2H5 CHZ CF3 ~ 89 ~

60 CZHS CH2-CF3 ~ 140 CI
6I CZHS CH2-CF3 ~ ( 127 mntries Ex. R' R2 R3 Melting No. point (°C) _ 62 C2H5 CHI-CF3 ~ ~ 120 63 C2H5 CH2-CF3 ~ I 143 CI
64 C~HS CHZ-CF3 i I 141 CH
65 C2H5 CH2-CF3 H3~ ~ I 3 152 66 CH2-CH=CH2 C1-i2-CF3 ~ ~ 125 OCHFZ
67 CH2-CH=CH2 CH2-CF3 ~ ~ 86 68 CH2-CH=CH2 CH2-CF3 ~ I CF3 108 . CA 02214752 1997-09-OS
- I.e A 3(1 930-Forei,.~1 countries Ex. R' R2 R3 Melting No. point (C) 69 CH2-CH= CHZ CHZ-CF3 ~ I 93 70 CH2-CH= CH2 CH2-CF3 ~ ~ 162 COOC3H, 71 CHZ-CH=CH2 CH2-CF3 ~ ~ 103 72 CH2 CH= CH2 CHa CF3 ~ I 144 OCZHS

73 CH2-CH =CH2 CH2-CF3 ~ I 110 Br 74 CHa-CH =CHI CH2-CF3 ~ I 115 75 CH2-CH =CH2 CH2-CF3 ~ ~ 126 76 CHz CH =CH2 CHi CF3 ~ ~ 118 - Le A 30 930-Foreign countries _ 4q. -Ex. Rl R2 R3 Melting No. , point (°C) 77 CH2-CH=CH2 CH2-CF3 ~ ~ 104 78 CH2-CH=CH2 CH2-CF3 ~ I 128 CI
79 C~~~-CH=CH2 CHZ-CF3 i I 119 CH
80 CH2-CH=CHa CHZ-CF3 H3G ~ I 3 123 scH3 'H-NMR
81 CH2-CH=CH2 CH2-CF3 ~ ( (CDC13, ~:
2.52 (s, SCH3), 6.13 (q, CH2_ CF3) ppm S~2CH3 82 CH2-CH=CH2 CH2-CF3 Ex. R' R2 R3 Melting No. point (°C) 83 ~ CH2-CF3 84 ~ CH2-CF3 85 ~ CH2-CF3 86 ~ CH2-CF3 oCHF2 1H-NMR
87 ~ CH2-CF3 ~ I (CDC13, b>:
4.74 (q, CH2CF3), 6.66 (t, OCHF~, ppm Bf 1s4~
88 ~ CH2-CF3 lss 89 ~ CH2-CF3 Ex. Ri R2 R3 Melting No. point (°C) 90 ~ CH2-CF3 I

91 ~ CH2-CF3 ~ I
SCZHS i t9 92 ~ CH2-CF3 ~ I
COOCzHS 116 93 ~ CH2-CF3 COOC3H~ n 114 94 ~ CH2-CF3 95 ~ CHI CF3 96 ~ CH2-CF3 ci - Le A 30 930-Foreign countries Ex RI R2 R3 Melting No. point (°C) 97 , ~ CH2-CF3 / SO -N~ 154 ( O-CH2 CH=CH2 98 ~ CH2-CF3 ~ ~ 117 CI
99 ~ CH2-CF3 ~ ~ 175 CI

100 CH3 - CHF2 ~ ~ 178 101 CH3 CHF2 ~ ~ 189 102 CH3 CHI-CF3 ~ I 142 103 CH3 CH2-CF3 ~ I COOCHZC=CH SS
104 CH3 . CH2-CF3 ~ oso2CH3 127 OCFZCHFZ
105 CH3 CH2-CF3 ~ I 128 w Ex. R' R2 R3 Melting point No. (°C) 106 '~"~ CHz-CF3 ~ OCFZCHFz ( 118 COOCsH~-f 107 CH3 CH=-CF3 ~ I 121 OCsH~-~
108 CH3 CH:-CF3 ~ I 118 OC3H~ i 109 '~ CH2-CF3 ~ I 79 OC~H~-n 110 CH3 CHI-CF3 ~ I 94 OC3HT-n Ill ~ CHZ-CF3 ~ ( 105 112 '-~ CHi-CF3 i I COOC3H, i 113 CH3 CH2-CF3 '~ CzH~ 167 I

H~N~N~CH3 N
O-CHZCF2CHFz Step 1: D ibutyltin bis-2, 2, 3, 3-tetrafluoropropoxide 723 g (2.45 mol) of dibutyltin dimethoxide with 777 g (5.89 mol) of 2,2,3,3-tetrafluoro-propanol are heated to 120°C under nitrogen. Most of the methanol liberated in this process is distilled off over a column. The remaining methanol and excess 2,2,3,3-tetrafluoro-propanol are then substantially removed under water pump vacuum (about 15 mbar), the dibutyltin bis-2,2,3,3-tetrafluoropropoxide remaining as residue.
Step ~: Bis-(2,2,3,3-tetrafluoropropyl) methyliminocarbonate At 40°C, 175 g (2.39 mol) of methyl isothiocyanate are added dropwise to dibutyltin bis-2,2,3,3-tetrafluoropropoxide obtained as described above, and the mixture is then heated under nitrogen to 120°C for 36 hours. The mixture is then subjected to a crude distillation, first under water pump vacuum and then under oil pump vacuum (final temperature in the bottom: 170°C at 1 mbar). Rectification under oil pump vacuum affords 555 g (77% of theory) of bis-(2,2,3,3-tetrafluoropropyl) methyliminocarbonate.
Boiling point: 73°C (15 mbar), purity: 98.3%

Le A 30 930-Foreign countries Step 3: 4-Methyl-5-(2,2,3,3-tetrafluoro-propoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one 555 g (1.83 mol) of bis-(2,2,3,3-tetrafluoropropyl) methyliminocarbonate are dissolved in X00 ml of tetrahydrofuran and, with ice cooling (0°C to 5°C), admixed with 18.7 g.(183 mmol} of pivalic acid (catalyst) and 278 g (1.83 mol) of phenyl carbazate. The mixture is stirred for 2 hours at 20°C and then warmed to 50°C, resulting in a crystal pulp that can be stirred only with difficulty. When this is heated to 80°C, the solution becomes homogeneous again. First, at about 200 mbar, most of the tetrahydrofuran and then, at about 15 mbar, most of the 2,2,3,3-tetrafluoro-propanol and phenol are distilled off. The residue is then freed of the remaining volatile components at a head temperature of 130°C and a pressure of about 0.5 mbar and then taken up in 400 ml of hot toluene. After cooling to 0°C, the crystalline product is isolated by filtration under suction.
280 g (67% of theory) of 4-methyl-5-(2,2,3,3-tetrafluoro-propoxy)-2,4-dihydro-1,2,4-triazol-3-one of melting point 141°C are obtained.

O
H~N~N~CH3 N

11.85 g (0.10 mol) of 4-methylurazole are dissolved in a mixture of 100 ml of isopropanol, 25 ml of water and 12 g of 45% strength aqueous sodium hydroxide solution (0.30 mol ofNaOH). At 40°C, difluorochloromethane (Frigen 22) is slowly passed through with stirring. After 27.7 g (0.41 mol) have been passed through, the reaction is interrupted and the reaction mixture is cooled. The isopropanol phase is separated off and concentrated under reduced pressure. The residue is stirred with diethyl ether and insoluble components are filtered off. The ether phase is concentrated under reduced pressure and the residue that remains is purified by preparative layer chromatography (eluent methylene chloride/methanol = 20/3).
0.9 g(5.5% oftheory) of5-difluoromethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 111°C is obtained.
By the methods of Examples (II-1) and (II-2), it is also possible to prepare, for example, the compounds of the formula (II) listed in Table 2 below.
O
H~N~N~R
(il) N
O-RZ

Table 2: Examples of compounds of the formula (II) Ex. R' R2 Melting No. point (C) II-4 CH3 CH~CC13 139 II-7 CH2-CH=CH2 CH2-CR3 62 II-8 ~ CH2-CF3 113 CH~--II-11 ~ CZHS CI-IF2 II-12 CHI-CH=CHI CHF2 II-13 ~ CHF2 II-14 CH3 CI-I(CF3)2 II-15 C2H5 CH(CF3)2 T.e A 30 930-Foreign co~?ntries Ex. R' R2 Melting No. point (°C) _ II-16 CH2-CH=CHa CH(CF3)2 II-17 ~ CH(CF3)2 II-18 ~H ~ CH(CF3)2 II-20 C~HS CH2-CH2-F

II-21 CH2-CH=CHZ CHZ-CH2-F

II-22 ~ CH2-CH2-F

CH2--.-II-26 N(CH3)2 CH2-CH2-F

T a 1~ 30 930-Foreign countries Ex. R' R2 Melting No. - point (°C) II-29 N(CH3)2 CH2-CF3 =

II-32 N(CH3)2 CHF2 II-34 C~HS CH2-CHF2 II-35 CH2-CH=CH2 CH2-CHF2 II-36 ~ CH2-CHF2 CHz-~ CH
H5C6'O/ 'N N 3 .
N=

At 20°C, 51.7 g (0.33 mol) of phenyl chloroformate are added dropwise with efficient stirring to a mixture of 59. I g (0.30 mol) of 4-methyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one, 100 ml of water, 400 ml of methylene chloride, 13.2 g (0.33 mol) of sodium hydroxide and 1.0 g of tetrabutylammonium bromide.
After the addition, stirring is continued for a further 16 hours and the organic phase is then separated o~ washed with water, dried and concentrated. The residue is crystallized from diisopropyl ether.
87.6 g (92% of theory) of 4-methyl-2-phenoxycarbonyl-5-(2,2,2-trifluoro-ethoxy)-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 105°C are obtained.
By the method of Example (IV 1) it is also possible to prepare, for example, the compounds of the formula (I~ listed in Table 3 below.

Le A 30 930-ForP,~~n ries count Table 3:3:
Examples of compounds of the formula (IV) Ex R' R2 Z Melting No. point (C) IV-2 ~ CH2-CF3 O-C6H5 91 IV 4 CH2-CH=CH2 CHI-CF3 O-C6H5 IV 6 C2H5 CHaCCI3 O-C6H5 IV 7 CH2-CH=CH2 CH2CC13 O-C6H5 IV-8 ~ CH2CC13 O-C6H5 IV N(CH3)2 CH2-CF3 O-C6H5 Ex R' R2 Z Melting No. point (C) IV CH2-CH=CHZ CH2-CF2-CHF2 O-C6H5 IV ~ CHz CF2-CHF2 O-C6H5 CHZ-Q
IU 19 N(CH3)2 CHZ CFA-CI~F2 O-C6H5 Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After 24 hours, the soil is watered with the preparation of the active compound. It is advantageous to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:
0% - no action {like untreated control) 100% = total destruction In this test, the compounds according to Preparation Examples 1, 2, 3, 4, 5, 6, 9, 1 l, 12, 15, 16, 17, 25, 50, 54, 66, 83, 84, 85, 86, 87, 88, 89, 91, 93, 94, 95, 96, 97, 98, 99, 100 and 101, for example, exhibit a strong action against weeds.

Table A: Pre-emergence test/ greenhouse Compound Applica-Bro- Lo- Poa Ama- Galin- Matri-Sina- Sola-of tion mus lium ranthussoga cariapis num Preparationrate Example (g/ha) No.

88 .125 90 90 90 80 95 95 80 90 Table A: (cont.) Compound Applica-Bro- Lo- Poa Ama- Galin-Matri-Sina-Sola-of tion mus lium ranthussoga caria pis num Preparationrate Example (g/ha) -Table A: (cont.) Compound Applica-Bro- Lo- Poa Ama- Galin-Matri-Sina-Sola-of tion mus lium ranthussoga caria pis num Preparationrate ', Example (gJha) Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 clri are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compounds desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compounds desired are employed in 2000 1 of water/ha. After three weeks, the degree of damage to the plants is rated in %
damage in comparison to the development of the untreated control.
The figures denote:
0% - no action (like untreated control) 100% = total destruction In this test, the compounds of Preparation Examples l, 2, 4, 5, 9, 16, 17, 25, 50, 66, 83, 84, 85, 86, 87, 88, 89, 93, 94, 95, 96, 98, 99 and 100 show a strong action against weeds.

Tahle B:B: Post-emergence test/greenhouse Compound flpplic-Alope-AvenaLo- Ama- DaturaGalium Heli- Sola-Vero-of ation Gurus lium ranthus anthusnum nica Preparationrate Example (g/ha) No.

100 . 125 - 90 80 90 90 90 - 95 90 Podosphaera test (apple)/protective Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 part by weight of alkyl-aryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated quantities 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 preparation of active compound. After the spray coating has dried on, the plants are inoculated by dusting with conidiae ofthe causative ~r~a";~", ~fa""tP ",;mP~x. ~n",~"~...,~,~o..~
,~.......~_:_L_~
--- - --~-__~___ ,.a rj,.... ~~~aa.wvr ~a vuvyr11av1ci lGlit;V6L1GL1CL~.
The plants are then placed in a greenhouse at 23°C and a relative atmospheric humidity of about 70%.
Evaluation is carried out 10 days after the inoculation.
In this test, the compounds of Preparation Examples l, 3, 83 and 85, for example, have an efficacy of 87 to 100% at an active compound concentration of 25 ppm.

- Le A 30 930-Foreign countries Table C:C:
Podosphaera test (apple)/protective Active compound (compound of ~ Effcacy in % of the untreated Preparation Example No.) control at an active compound concentration of 25 ppm 3 g~
$3 100 Exam lp a D
Sphaerotheca test (cucumber)/protective Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 part by weight of alkyl-aryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated quantities 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 preparation of active compound. After the spray coating has dried on, the plants are dusted with conidiae of the fungus Sphaerotheca fuliginea.
The plants are then placed in a greenhouse at 23 to 24°C and at a relative atmospheric humidity of about 75%.
Evaluation is carried out 10 days after the inoculation.
In this test, the compound of Preparation Example 50, for example, has an efficacy of 92% at an active compound concentration of 100 ppm.

' Le A 30 930-Forei,~;n countries :able D
Sphaerotheca test (cucumber)/protective Active compound (compound of E~cacy in % of the untreated Preparation Example No.) control at an active compound concentration of 100 ppm 50 9~

Claims (25)

CLAIMS:

1. A sulphonylaminocarbonyltriazolinone having a halogenalkoxy substituent of the general formula (I):

wherein:
R1 represents: (i) H, hydroxyl, amino or C1-C6-alkylideneamino, (ii) optionally F-, Cl-, Br-, cyano-, C1-C4-alkoxy-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted C1-C6-alkyl, (iii) optionally F-, Cl-, Br- or a combination thereof-substituted C2-C6-alkenyl or C2-C6-alkynyl, (iv) optionally F-, Cl- or a combination thereof-substituted C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkylamino, di-(C1-C4-alkyl) -amino or C1-C4-alkanoylamino, (v) optionally F-, Cl-, Br-, C1-C4-alkyl- or a combination thereof-substituted C3-C6-cycloalkyl or C3-C6-cycloalkyl-C1-C4-alkyl, or (vi) optionally F-, Cl-, Br-, cyano-, nitro-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy-, C1-C4-alkoxy-carbonyl- or a combination thereof-substituted phenyl or phenyl-C1-C4-alkyl;

R2 represents -CH2-CF3, -CH2-CCl3 or -CH2-CF2-CHF2;
and R3 represents:

wherein:

R4 and R5 are identical or different and each represent: (i) H, F, Cl, Br, I, nitro, C3-C6-alkynyloxy, C3-C6-alkynylthio, phenyl, phenoxy, C1-C4-alkyl-carbonylamino, Cl-C4-alkoxy-carbonylamino, C1-C4-alkoxyamino-carbonyl-amino, di-(C1-C4-alkyl)-amino-carbonylamino, trimethylsilyl, thiazolinyl, C1-C4-alkyl-sulphonyloxy or di-(C1-C4-alkyl)-aminosulphonylamino, (ii) optionally F-, Cl-, Br-, cyano-, carboxyl-, C1-C4-alkoxycarbonyl-, C1-C4-alkylamino-carbonyl-, di-(C1-C4-alkyl)-amino-carbonyl-, hydroxyl-, C1-C4-alkoxy-, formyloxy-, C1-C4-alkyl-carbonyloxy-, C1-C4-alkoxy-carbonyloxy-, C1-C4-alkylamino-carbonyloxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, di-(C1-C4-alkyl)-aminosulphonyl-, C3-C6-cycloalkyl- or phenyl-substituted C1-C6-alkyl, (iii) optionally F-, Cl-, Br-, cyano-, C1-C4-alkoxy-carbonyl-, carboxyl- or phenyl-substituted C2-C6-alkenyl or C2-C6-alkynyl, (iv) optionally F-, Cl-, Br-, cyano-, carboxyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted C1-C4-alkoxy, (v) optionally F-, Cl-, Br-, cyano-, carboxyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted C1-C4-alkylthio, (vi) optionally F-, Cl-, Br-, cyano- or C1-C4-alkoxy-carbonyl-substituted C2-C6-alkenyloxy, (vii) optionally F-, Cl-, Br-, cyano-, nitro-, C1-C3-alkylthio- or C1-C4-alkoxycarbonyl-substituted C2-C6-alkenylthio, or (viii) -S(O)p-R6, CO-R8 or -CH=N-R9, wherein:

p represents 1 or 2, R6 represents: (i) optionally F-, Cl-, Br-, cyano-or C1-C4-alkoxy-carbonyl-substituted C1-C4-alkyl, (ii) C3-C6-alkenyl, C3-C6-alkynyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkylamino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino or phenyl, or (iii) -NHOR7, wherein:

R7 represents: (i) optionally F-, Cl-, cyano-, C1-C4-alkoxy-, C1-C9-alkylthio-, C1-C4-alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkylamino-carbonyl- or di- (C1-C4-alkyl) -amino-carbonyl-substituted C1-C12-alkyl, (ii) optionally F-, Cl- ar Br-substituted C3-C6-alkenyl, (iii) optionally F-, Cl-, nitro-, cyano-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C4-alkoxy-carbonyl-substituted C3-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl or phenyl-C1-C2-alkyl, or (iv) optionally F-, Cl-, nitro-, cyano-, C1-C4-alkyl-, trifluoromethyl-, C1-C4-alkoxy-, C1-C2-fluoroalkoxy-, C1-C4-alkylthio-, trifluoromethylthio- or C1-C4-alkoxy-carbonyl-substituted benzhydryl or phenyl, R8 represents: (i) H, or (ii) optionally F-, Cl-or a combination thereof-substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C4-alkylthio, C1-C4-alkyl amino, C1-C4-alkoxyamino, C1-C4-alkoxy-C1-C4-alkylamino or di- (C1-C4-alkyl) -amino, and R9 represents: (i) optionally F-, Cl-, cyano-, carboxyl-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted C1-C6-alkyl, (ii) optionally F- or Cl-substituted benzyl, C3-C6-alkenyl or C3-C6-alkynyl, (iii) optionally F-, Cl-, Br-, C1-C4-alkyl-, C1-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy- or trifluoromethylthio-substituted phenyl, (iv) optionally F-, Cl- or a combination thereof-substituted C1-C6-alkoxy, C3-C6-alkenoxy, C3-C6-alkinoxy or benzyloxy, (v) amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino, phenylamino, C1-C4-alkyl-carbonylamino, C1-C4-alkoxy-carbonylamino or C1-C4-alkyl-sulphonylamino, or (vi) optionally F-, Cl-, Br- or methyl-substituted phenylsulphonylamino;

wherein:
R10 represents H or C1-C4-alkyl, R11 and R12 are identical or different and each represent: (i) H, F, Cl, Br, nitro, cyano, carboxyl, C1-C4-alkoxy-carbonyl, dimethylaminocarbonyl, C1-C4-alkyl-sulphonyl or di-(C1-C4-alkyl)-aminosulphonyl, or (ii) optionally F-, Cl- or a combination thereof-substituted C1-C4-alkyl or C1-C4-alkoxy; or wherein:
R19 and R20 are identical or different and each represent: (i) H, F, Cl, Br, cyano, nitro, di-(C1-C4-alkyl)-amino-sulphonyl, C1-C4-alkoxy-carbonyl or dimethylaminocarbonyl, (ii) as defined for R11 and R12, or (iii) optionally F-, Cl- or a combination thereof-substituted C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl;
or a sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di- (C1-C4-alkyl) -ammonium, tri- (C1-C4-alkyl) -ammonium, tetra- (C1-C4-alkyl) -ammonium, tri- (C1-C4-alkyl) -sulphonium, C5- or C6-cycloalkyl-ammonium or di- (C1-C2-alkyl) -benzyl-ammonium salt thereof.

2. A compound according to claim 1, wherein:
R1 represents: (i) optionally F-, Cl-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, (ii) optionally F-, Cl-or Br-substituted propenyl, butenyl, propynyl or butynyl, (iii) optionally F-, Cl- or a combination thereof-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, propenyloxy or butenyloxy, (iv) methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino, (v) optionally F-, Cl-, Br-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or (vi) optionally F-, Cl-, Br-, cyano-, methyl-, trifluoromethyl- or methoxy-substituted benzyl or phenyl;
R2 is as defined in claim 1; and R3 represents:

wherein:
R4 represents F, Cl, Br, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy, methoxycarbonyl, ethoxycarbonyl, or n- or i-propoxycarbonyl, and R5 represents H, methyl, ethyl, F, Cl or Br;

wherein R11 represents F, Cl, Br, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl; or wherein R represents methyl, ethyl, or n- or i-propyl.

3. A compound according to claim 1, wherein R1 is CH3, R2 i s CH2CF3 and R3 is:

4. A compound according to claim 1, wherein R1 is CH3, R2 is CH2CF3 and R3 is:

5. A compound according to claim 1, wherein R1 is CH3, R2 is CH2CF3 and R3 is:

6. A compound according to claim 1, wherein R1 is CH3, R2 is CH2CF3 and R3 is:

7. A compound according to claim 1, wherein R1 is CH3, R2 is CH2CF3 and R3 is:

8. A compound according to claim 1, wherein R1 is CH3, R2 is CH2CF3 and R3 is:

9. A compound according to claim 1, wherein R1 is CH3, R2 is CH2CF3 and R3 is:

10. A compound according to claim 1, wherein R1 is C2H5, R2 is CH2-CF3 and R3 is:

11. A compound according to claim 1, wherein R1 is R2 is CH2-CF3 and R3 is:

12. A compound according to claim 1, wherein R1 is R2 is CH2-CF3 and R3 is:

13. A herbicidal or fungicidal composition comprising a herbicidally or fungicidally effective amount of a compound according to any one of claims 1 to 12 in admixture with a suitable carrier or diluent.

14. A herbicidal or fungicidal composition comprising a herbicidally or fungicidally effective amount of a compound according to any one of claims 1 to 12 in admixture with a solid diluent or carrier, a liquified normally gaseous diluent or carrier, or a liquid diluent or carrier containing a surface active agent.

15. A method of combating weeds or combating fungi which comprises applying to the weeds or fungi, or to a habitat thereof, a herbicidally or fungicidally effective amount of a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14.

16. A method of combating weeds or combating fungi which comprises applying to the weeds or fungi, or to a habitat thereof, a herbicidally or fungicidally effective amount of a composition containing between 0.1 to 95% by weight of a compound according to any one of claims 1 to 12 in admixture with a suitable carrier or diluent

17. A method of combating weeds or combating fungi which comprises applying to the weeds or fungi, or to a habitat thereof, a herbicidally or fungicidally effective amount of a composition containing between 0.5 to 90% by weight of a compound according to any one of claims 1 to 12 in admixture with a suitable carrier or diluent

18. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14, wherein the compound or composition is applied as a pre-emergence herbicide.

19. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14, wherein the compound or composition is applied as a post-emergence herbicide.

20. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14, wherein the compound is applied to an area of cultivation at a rate of between 1 g and 10 kg/ha.

21. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 12, or a composition according to claim 13 or 14, wherein the compound is applied to an area of cultivation at a rate of between 5 g and 2 kg/ha.

22. A process for preparing a compound of the general formula I as defined in any one of claims 1 to 12, or a salt thereof, which process comprises:
(a) reacting a triazolinone of the general formula (II):
wherein R1 and R2 are as defined in any one of claims 1 to 12, with a sulphonyl isocyanate of the general formula (III):
R3-SO2-N=C=O (III) wherein R3 is as defined in any one of claims 1 to 12; or (b) reacting a triazolinone derivative of the general formula (IV):
wherein R1 and R2 are as defined in any one of claims 1 to 12, and Z represents a halogen atom, alkoxy, aralkoxy or aryloxy, with a sulphonamide of the general formula (V):
R3-SO2-NH2 (V) wherein R3 is as defined in any one of claims 1 to 12; or (c) reacting the triazolinone of the general formula (II) as defined in step (a) with a sulphonamide derivative of the general formula (VI):
R3-SO2-NH-CO-Z (VI) wherein R3 is as defined in any one of claims 1 to 12, and Z
is as defined in step (b); or (d) reacting the triazolinone of the general formula (II) as defined in step (a) with a sulphonyl halide of the general formula (VII):
R3-SO2-X (VII) wherein R3 is as defined in any one of claims 1 to 12, and X
represents a halogen atom, and a metal cyanate of the general formula (VIII):
MOCN (VIII) wherein M represents an alkali metal equivalent or an alkaline earth metal equivalent; or forming a salt as defined in claim 1 of a compound obtained in step (a), (b), (c) or (d).

23. A process for preparing a herbicidal or fungicidal composition which comprises admixing a compound according to any one of claims 1 to 12 with an extender or surface-active agent.

24. A triazolinone of the general formula (II):
wherein R1 and R2 are as defined in any one of claims 1 to 12.

25. A triazolinone derivative of the general formula (IV):
wherein:
R1 and R2 are as defined in any one of claims 1 to 12; and Z represents F, Cl, Br, methoxy, ethoxy, benzyloxy, phenoxy, or a halogeno- or nitrophenoxy.