IE61260B1 - Substituted triazolinones - Google Patents

Abstract

Novel substituted triazolinones of the formula (I) in which R<1> represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, tetrahydrofuranyl, tetrahydrofuranylalkyl, or in each case optionally substituted aralkyl or aryl, R<2> represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkenyl, alkylaminoalkyl, dialkylaminoalkyl or in each case optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or in each case optionally substituted heterocyclylalkyl, or in each case optionally substituted aralkyl, aroyl, aryl, aralkyloxy or aryloxy, or represents alkoxy, alkenyloxy or alkynyloxy, X represents oxygen or sulphur and Y represents oxygen or sulphur, a process for the preparation of these compounds, and their use as herbicides.

Description

Substituted trlagolinonea The invention relates to new substituted triazoliaonea, severs! processes for their preparation and their use as herbicides.

It has been disclosed that certain nitrogen heterocycle® such as, for example, 4-amino-3-methyl-6-phenyl-1,2,,4triazin-5-one or N-isobutyl^-oxiioid&ssolidiae-l-c&rboxamide (compare, for example, DS-OS (German Published Specification) 2,354,474 and R. Wagler ’Ghesaie der 10 Pflaaaenschuts- und Schadlingsbekampfungsmittel (Chemistry of Plant Protection Agents and Pesticides) Volume 5, 219 (1977)) possess herbicidal properties.

However, the herbicidal activity of these previously known compounds with respect to problem weeds as well as their tolerability with respect to important cultivated, plants is not completely satisfactory in all areas of application.

JP-A-52/125,16S describes 4-asaiao-3-alk(en/ia)yl-l,2,4triazolin-5-oae derivatives, their synthesis and also their use as herbicides.

Furthermore, certain .'substituted triassolinones, such as, for example, l-(sr,N-dimethylcarbamoyl)-3-pheayl-4-aaiaol,2,4-triasolia-5-oae have been disclosed (compare J. Hefcerocycl., Chem. 17., 1691-1696 [19802? Org. Mass.

Spectra». 14, 369-378 (19793). Nothing has hitherto been disclosed about a herbicidal activity of these previously known triasoliaonss.

New substituted triagoliaor.es of the general formula (15 (I) R111 k I ''NHNH-R2 in which R1 represents hydrogen, in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atoms and I to 15 identical or different halogen atone, halogenoalkiayl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl having 1 to S carbon atoms in the individual alkyl moieties, eycloalkyl or cyeioalSeylalfeyl in each case having 3 to 7 carbon atoms in the cycloalkyl moiety and optionally 1 to 6 carbon atoms in the straightchain or branched alkyl moiety, aryl having 6 to 10 carbon atoms in the aryl moiety, which is monosubstituted or polysubstituted by identical or different substituents, suitable aryl substituents in each case being: halogen, cyano, nitro and ia each case straightchain or branched alkyl, alkoxy, alkylthio, halogeaoalkyl, halogeaoalkoxy or halogenoalkylthio in each case having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms, B2 represents hydrogen, in each case straight-chain or branched alkyl having 1 to IS carbon atoms, alkenyl having 2 to 8 carbon atoms, alkimyl having 2 to 8 carbon atoms, halogeaoalkyl having 1 to S carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl ia each case having 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, hvdroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl . ia each case having up to 6 carbon atoms in the individual alkyl or alkenyl moieties, alkylaminoalkyl or dialkylaiainoalkyl in each case having 1 to 6 carbon atoms in the Individual alkyl moieties, cycloalkyl having 11 carbon atoms or cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl in each case having 3 to 8 carbon atoms in the cycloalkyl or eycloalkeayl moiety and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, in each case optionally mono» substituted or · polysubstituted by identical or different substituents, suitable substituents in each case being: halogen, cyano and in each case straight-chain or branched alkyl or halogeaoalkyl in each case having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms or straight-chain or branched halogeaoalkenyl having up to 4 carbon atoms and 1 to 5 identical or different halogen atoms or in each case doubly linked alkaaediyl or alkenediyl in each ease having up to 4 carbon atoms; B? additionally represents heterocyclylalkyl having 1 to 6 carbon atoms in the straight-chain ox branched alkyl moiety and 1 to 9 carbon atoms and also 1 to 3 hetero atoms - in particular nitrogen, oxygen and/or sulphur - in the heterocyclyl moiety and which is optionally monosubstituted or polysubstituted in the heterocyclyl moiety by identical or different substituents, suitable substituents being: halogen, cyano, nitro, and ia each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeaoalfeyIthio or alkoxyoarbcnyl in each ease having 1 to 5 carbon ators and optionally 1 to 9 identical or different halogen atoms; 32 additionally represent© in each case straight-chain or branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms and finally aralkyl, aroyl,, aryl, aralkyloxy or aryloxy, in each case having 6 to 10 carbon atoms in th® aryl moiety and optionally 1 to 8 carbon atoms in the alkyl moiety, and in each case optionally monosubstituted or polysubstituted by identical or different substituents, suitable alkyl substituents optionally being halogen and cyano and suitable aryl substituents in each case being: halogen, cyano, nitro, hydroxyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, IS halogenoalkyl, aalogenoalkoxy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkyleulphinyl, halogenoalkyl sulphonyl, alkanoyl or alkoxycarbonyl in each case having 1 to 6 carbon, atoms is the alkyl moiety .and optionally 1 to 9 identical or different halogen atoms, cycloaikyi having 3 to 6 carbon atoms and phenoxy, X represents oxygen or sulphur and T represents oxygen or sulphur, have been found.

Th© compounds of the formula Cl) can optionally exist as geometric and/or optical isomers or isomer mixtures of different composition, depending on the nature of the substituents 31 and R2. Both the pure isomers and the isomer mixtures are claimed according fco the invention...

Furthermore, it has been found that the aew substituted triasolineraes of the general formula (X) in which R1 represents hydrogen, in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon, atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to 8 carbon atom® and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, alkoxyalkyl having 1 to β carbon atoms in the individual alkyl moieties, eycloalkyl or cycXoalfcyXaXkyl ia each ease having 3 to 7 carbon atoms in the eycloalkyl moiety and optionally 1 to 6 carbon atoms in the straightchain or branched alkyl moiety, aryl having 6 to 10 carbon atoms ia the aryl moiety, which is monosubstituted or polysubefcitnfced by identical or different substituents, suitable aryl substituents in each case being: halogen, cyano, nitro and ia each case straightchain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogeeaoalkylfcSsio in each case having 1 ts 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms, Br represents hydrogen, in each case straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, Saalogenoalkyl having 1 t© S carbon atcws and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl in each case having 2 to 8 carbon atoms and 1 to 15 or 13 identical ox* different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarboaylalkyl or alkoxycarboaylalkenyl in each case having up to 6 carbon atoms in the individual alkyl or alkenyl moieties, alkylaminoalkyl or dialkylaminoalkyl in each case having 1 to S carbon atoms in the individual alkyl moieties, cycloalkyl having 11 carbon atoms or cycloalkyl, cyeloalkylalky'l, cycloalkenyl or cycloalkenylalkyl in each case having 3 to 8 carbon atoms In the cycloalkyl or cycloalkenyl moiety and optionally 1 fco 6 carbon atoms In the straight-chain or branched alkyl moiety, in each ease optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents in each case being: halogen, cyan© and in each case straight-chain or branched alkyl or halogeaoalkyl In each case having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms or straight-chain or branched halogenoalkenyl having up to 4 carbon atoms and 1 to 5 identical or different halogen atoms or In each case doubly linked alkanediyl or alkenediyl In each case having up to 4 carbon atoms; ΒΓ additionally represents heterocyelylalkyl having 1 fco S carbon atoms la the straight-chain or branched alkyl moiety and X to 9 carbon atoms and also 1 to 3 hetero atoms - In particular nitrogen, oxygen and/or sulphur - In the heterocyclyl moiety and which is optionally monosubstituted or polysubstituted in the heterocyclyl moiety by Identical or different substituents, suitable substituents beings halogen, cyano, nitro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogesaoalkyl, halogenoalkoxy, halogeaoalkylthi© or alkoxycarbonyl in each ease having 1 to 5 carbon atoms and optionally 1 to 9 Identical or different halogen atoms; B2 _ 7 additionally represents in each case straight-chain or branched alkoxy having X to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms and finally aralkyl, S aroyl, aryl, aralkyloxy or aryloxy, in each case having 6 to 10 carbon atoms in the aryl moiety and optionally 1 to 8 carbon atoms in the alkyl moiety, and in each ease optionally monosubs ti tuted or polysubstituted by identical or different substituents, suitable alkyl substituents optionally being halogen and cyano and suitable aryl substituents in each case being: halogen, cyano, nitro, hydroxyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogeaoalkyl, halogenoaikoxy, halogenoIS alkylthio, alkylsulphinyl, alkylsulphonyl, halogeaoalkylsulphinyl, halogeaoalkylsulphonyl, alkanoyl or alkoxycarbonyl in each case having 1 to 6 carbon atoms in the alkyl moiety and optionally 1 to 9 identical or different halogen atoms, cycloalkvl having 3 to 6 carbon atoms and phenoxy, X represents oxygen or sulphur and v represents oxygen or sulphur, are obtained when ia) hydrazones of the formula (II) Rx\-N II J in which Rx, R2, X and T have the abc#veaentioned meaning and S3 and ST1 independently of one another in each case represent hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, or phenyl or benzyl, are reacted with an acid, if appropriate in the presence of a diluent, or when (b) IS-triasolinoaes of the formula (III) (III) in which 31 .and H have the ahovesaentionad meaning, are reacted with iso (thio) cyanates of the formula (IV) ES-N=C='? (IT) in which Ba and Z have the aboveaaeationed meaning, if appropriate In the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or when (c) triasolinones of the formula (V) CV5 in which X and Y have the abovementioned meaning, and R5 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms or phenyl or . benzyl, optionally aonosubstituted to tri subs titrated by identical or different substituents, suitable substituents In each case being: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio In each case having 1 to 4 carbon atoms or in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkyl thio in each ease having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, with amines of the formula (VI) ST-ΝΞ, (VI) in which RJ has the .abovementioned meaning, if appropriate In the presence of a diluent and If appropriate in the presence of a reaction auxiliary.

Finally, It has been found that the new substituted triazoliaones of the general formula (I) possess herbicidal properties.

Surprisingly, the substituted trlasolinones of the general formula (I) according to the Invention shew a considerably higher herbicidal potency against problem weeds than the nitrogen beteroeycles known from the prior art, such as, for example, 4-amino-3-methyl-6-phenyll,2,4-triasln-5-one, which are related cceapowads chemically and with respect to action.

Formula (I) provides a general definition of the substituted triezolinones according to the invention. Preferred compounds of the formula (I) are those in which R1 represents hydrogen, methyl, ethyl, a- or i-propyl, η-, 1-, s- or t-butyl, a- or i-pentyl, a- or i-hexvl, allyl, propargyl, straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and I to 9 identical or different halogen atoms, in particular fluorine, chlorine or bromine, methoxymethyl, ethoxymethyl, prqpoxymethyl, cydopeatyl, cyclohexyl, cyclopropyl, cyclopropy Ime thyl, cyclohexylmethyl, cyclohexylethyl, for phenyl which is optionally saoaosubstituted to trisubstltuted by identical or different substituents, suitable substituents beings fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, s- or i-propyl, η-, 1-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, tri£luoromethoxy or trifluoromethylthio, R2 represents hydrogen, methyl, ethyl, s- or i-propyl, η-, 1-, s- or t-butyl, ia each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, allyl, in each case straight-chain or branched butenyl, peateayl or hexenyl, propargyl, in each ease straight-chain or branched buiiayl, pentinyl or hexinyl, straight-chain er branched halogeaoalkyl having 1 to 8 carbon atoms and 1 to S identical or different halogen atoms, in particular fluorine, chlorine or bromine, is. each case straight-chain or branched halogeaoalfceayl or halogenoakysayl is each case having 3 to 8 carbon atoms and 1 to 3 halogen atcsss, in particular fluorine or chlorine, la each case straight-chain or branched cyanoalkyl having I to S carbon atoms In the alkyl moiety, hydroxyalkyl having 1 to 6 carbon atoms and 1 to 3 hydroxyl groups, alkoxyalkyl, alkosqrcarbonyl11 alkyl or alkoxyearbonylalkenyl, alkylamino&lkyl or dialkylaminoalkyl in each case having up to 4 carbon atoms in the individual alkyl or alkenyl moieties or cyclopropyl, cyclopropy Ime thyl, cyclopropyl ethyl, cvclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclohexyImethyl, cyclohexylethyl, cyclohexenyl or eye lohexeny Ime thyl, in each case optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents in each case beings fluorine, chlorine, bromine, asthyl, ethyl, a- or i-propyl, a-, i-, ©- or t-butyl, cyano, methanediyl, ethanediyl, butanediyl or butadienediyl or dichloroallyl; R3 furthermore represents heterocyclylmethyl, heterocyclylpropyl or heterocyclylethyl which are optionally monosubstituted to trisubstituted in the heterocyclyl moiety by identical or different substituents, suitable heterocycles ia each ease beings Z ia each ease representing oxygen or sulphur and suitable substituents in each case beings fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, a- or i-propyl, a-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoro«ethoacy or trifluoreraethylthio; Ea additionally represents ia each case straight-chain ©r branched alkoxy having 1 to 6 carbon atoms, alkenyloxy having 3 to S carbon at-aeas ©r alkiayloxy having 3 t© 6 carbon atoms or optionally straightchair, or branched benzyl, phenylethyi, phenylpropyl, phenyIbutyl, phenyIpentvl, phenyIhexvl , phenylheptyl, phenyIcyanomethyl, phenylcyanoethyl, phenylcyanopropyl, benzyloxy, phenylethoxy, phenoxy, benzoyl, phenyl or naphthyl, in each case optionally monosubstituted to trxsubstituted by identical or different substituents, suitable phenyl substituents in each case being: fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, a- or i-propyl, η-, I-, e- or t-butyl, methoxy, ethoxy, methyl thio, trif luoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl, trif luoromethylsulphonyl, ae thyl sulphinyl, methylsulphonyl, acetyl, propionyl, saethoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenoxy, Z represents oxygen or sulphur and T represents oxygen or .sulphur...

Particularly preferred compounds of the formula (I) are those ia which B1 represents hydrogen, methyl, ethyl, a- or i-propyl, methoxymethyl, ethoxyraethyl or propoxymethyl, R3 represents hydrogen, or represents methyl, ethyl, aor i-propyl, a-, I-, s- or t-butyl, allyl, propargyl, in each esse straight-chain or branched pentyl, hexyl, heptyl, octyl, hntenyl, pentenyl, butinyl or pentinyl or hexiayl, each, of which is optionally aoaosuhstltuted, disubstituted or trisubstituted by fluorine and/or chlorine,; or additionally represent® cyclopropyl, cyclopentyl, cyclohexyl, cyclohexenyl, eyclopropylsethyl, cyclo30 propylethyl, cyclohexylsethyl, cyclohexyl ethyl or cycloheptyl which are in each case optionally xxssubstituted, disubstituted or trlsubsfcituted by identical or different swbstitueafce from the group comprising fluorine, chlorine, methyl, ethyl and/or cyano and finally represents benzyl, phenylethyl or phenyl, X represents oxygen or sulphur and Y represents oxygen or sulphur» The following substituted triazolxnoaes of the general formula (I) ι | Λ (X) nh-R2 may be mentioned individually ia addition to the compounds mentioned ia the preparation examples: ET ΟΠch3 *·**»* pi1® VdSL^ cs3 CHC(CH3)3 -Cics3)3 -/TN 1^3 .S -C(CH3)3 ~c(ch3)3 C-f 1 '4 V?3 / 3 0 S S 0 IS «I «!·»*? ^2¾ ^2~5 CJ W ^-a^s Ja ja •p ΓΊΟ* _r ίΠ®· '3 %«<· 'W3 p-'· *1 % m » CHg I 3 CBg ^4¾ -CH-CiK I ch3 ch3 CH3 I ,xzh3 PVi«, Μαλ GS, -CH—CH-C9Hc I j · ~ 5 CE o> Ci Ca - IS a2 CHCHCHCH- CH-cCH-CH-C,HS ~ tfWHi <« ch3 I ~ ch3 CH γη3 7"3 I I -c-c~ch3 I Ϊ CH-a CH-, I -'C-CH-s-K j ^...CK3 -CH-C00C2H3 CH CH-CB2~CH2-CH~ί ch2)2-ch3 CH-a Cw to « «3 -CH< cch2)2-ch3 {£e &b **>> C^He I Ce e 2H5 Cii v dIS> CH CS CE f9* **» '3 '3 CH -ch2-c <.y*iw.i — iftr CH/ x._ ci Cl <0 'V R a a wjy»J Vow»»·; CH •ch-(C«2)3~ch3 C? «Β 2rt5 2)2-CH3 C «JlJrtg CHO (CH2)3-CH< CH< CHch3 I CH"CH3 ch*ch3 I Cri3 CH«a w -C; , gw % OCH -a e-J och3 - 19 ET Βch3 ΟΗJC_ o -C-C: R configuration CH '«"4 s) ch3 S coaxIguration Vi·»»·’» -CH-CH CHCEL CHCHg CK~CH->-GCH3 I C fr***·» ue,B3 ’iCH2)2~GHg -CH< CHCHg CK^-CH € L.S-5 C’ wL •CH-C^Hc g m «* CHg f» %!»«··« *?J '**3 <] (CH2>2~CH3 iCHgig-CHg (?W£$ CH2"CK< CMCH20 -ch-c2h CH If, for example, 1-(N-isobutylcarbemoyl)-4-isopropylidenei2ainO"3-methyl-l,2,4-triazolin-5-one is used as the starting compound, then the course of the reaction os process (a) according to the invention can be represented by the following equation: ^ch3 II I CH. Η20/Ηθ -(ch3)2co NH-CH2~CBCCH332 K 2 O'jj~ch2~ch3)2 If, for example, 4-amino-3-methyl-X,2,4-(1H>-triazolin-5one and t-butyl isocyanate are used as starting substances, in the course of the reaction of process (b) according to the invention can be represented by the following equation: CH,x.-Κ>·ΝΉ2 II j ’ - 3)3c-n=oo H 3 II I " O=C"HH-C(CH3)3 If, for 'example, 1 -ethoxycarbonyl-4-amino-3-methyl-1,2,4triasolin-5-one and 2?,H-diethylpropane-l,3-diaaaine are used as starting substances, then the course of the reaction of process (c) according to the invention can be represented by th® following equation: h2n-ch2-ch2-ch2-n< iM I o=c-oc2h5C2H5 C2H5 - C2H5-OH CH -5^-Ν-ΉΗ-, 3 Tl I o=c-nh~ch2-ch2-ch2-n < C2H5 C2H5 Formula (IX) provides a general definition of the hydra5 sones required as starting materials for carrying out process (a) according to th® invention. Xn this formula (II), H1, Ra, Z and Ύ .preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention. The hydrazones of the formula (Hi were hitherto uakrowa excluding the compound 1- (N-4-broxnophenylthiocarbamoyl) -4-phenylifieaeassiao1,2,4-fcriazoliae-5-thioae.

They are likewise a subject of the present invention. However, they are obtained analogously to known processes (compare, for example, Acta Pol. Pharwu 38,, 153-162 [19813 or C.A. 95: 203841J), for example when X-uasufostituted 4-amiao-triazolinones of the formula (IZI> H Isa which Br and 2 have the ahoveaesfioaed meaning, are reacted with aldehydes or ketones of the formula (VII) (VII) in which R3 and 3*' have the abovementioned meaning, if appropriate in th® presence of a diluent such as, for 5 example, dichloromethane or toluene, and if appropriate in the presence of a catalyst such as, for example, p-toluenesulphonic acid, at temperatures between 40°C and 120°C, and the 1-unsubstituted triazoliaone-hydrazones of the formula {VIII) w (VIII) la which Rx, r3, r* and X have the abovementioned meaning, thus obtainable are reacted la a subsequent 2nd step with iso (thio) cyanates of the formula (IV) (IV> in which R3 and 1 have the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, dichloromethane or dioxane, and if appropriate is the presence of a reaction auxiliary such as, for example, triethylamine, at temperatures between 50°C asd 150®C. or alternatively reacted Is a subsequent 2nd step with (thio)chloroformates of the formula (IX) II R5-O-C-C1 ( IX) in which Rs and Y have the abovementioned meanings, if appropriate in the presence of a diluent such as, for 5 example, tetrahydrofuraa and if appropriate ia the presence of a reaction auxiliary such as, for example, sodium hydride or potassium t-butoxide, at temperatures between - 20°C and * 40°C and the triaxolinones of the formula (Z) Y«e-o-R5 la which R1, R3, R*, Rs, Z and ¥ have the abovementioned meaning, thus obtainable are reacted In a subsequent 3rd step with amines of the formula (VI) (vl) in which B2 has the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, tetrahydrofuraa and if appropriate in the presence of a base such as, for example, sodium hydroxide or potassium hydroxide, at temperatures between 20®C and 50&C.

It is also possible here and may be advantageous to carry out the reaction of the 1-unsubstituted triazolinone hydrazones of the formula (win) •with (thio) chloroformates of the formula (IX) and the subsequent reaction of the triazolinones (X) thus obtainable with amines of the formula (VI) in one reaction step in a so-called one-pot process (of. Example 3) .

The 1-unsubstituted 4-amino-triazolinones of the formula (III) are known or obtainable analogously to known processes (compare, for example, J. Beterocycl. Chem. 16, 403 [19793 ? J. Seterocycl. Chem. 17, 1691 [19803 ? Surop, J. Med. Chem,. 18, 215 [1983] ,- Chem. Ber, 98, 3025 [19653 or Liebigs Ann. Chem. 637, 135 [19603 ).

The aldehydes or Ice tones of the formula (VII) are generally known compounds of organic chemistry.

The l-uasubsfcituted triazolinone hydrazones of the formula (VIII) are in the main known (compare, for example, pj„ Seterocycl. Chess. 20, 77-80 [19833 ? J. Seterocycl. Chem. 16, 403-407 [19793; Chim. Acta.

Ture. 7, 269-290 [19793? J- ehem. Soc.; Rerkia Trans. II, 1973, 9-11? J. org. Chem. 36, 2190-2192 [1971]).

The (thio) chloroformates of the formula (IX) are generally known compounds of organic chemistry.

The triazolinones of the formula (Σ) mentioned as infcer25 mediates are known in some cases (compare, for example, Acta. Pol. Pham. 38, 153-162 [19813 and C.A. 95 s 2030413).

Still unknown and likewise a subject of the present application are triazolinones of the formula (Xa) Y«C-O-R5 in which represents straight-chain or branched alkyl having 1 to 4, in particular having 1 to 3, carbon atoms; very particularly preferably R1’1 represents methyl, S and R’, R*, R’, X and T have the abovementioned meanings, 3s preferably represents methyl, ethyl, a- or i-propyl, η-, I-, s- or t-butyl or phenyl or benzyl which are optionally monosubstituted to disubstituted by identical or different substituents, suitable substituents In each case being: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, η-, I-, s- or t-butyl, methoxy, ethoxy, nor i-propoxy, saethylfchio, trisluorosaethyl, tri15 fluoroaethoxy or trifluorosaethylthio; Z .and "f in each case independently of one another represent oxygen and. sulphur, preferably oxygen.

Formula (III) provides a general definition of the 20 ΙΞ-triasoliaoaes required as starting materials for carrying out process (b) according to the invention. In this formula (III), R1 and X preferably represent those radicals which have already been Mentioned as preferred for these substituents In connection with the description of the substances of the formula (I) according to the invention.

The l-fcriazoXinoaes of the formula, (III) are know® or obtainable analogously to known processes (compare, for example, J. Heterocycl. Chem. 16, 403 [1979]; J. Heterocycl. Chem. 17, 1691 [19803 ; Burop. J. Med. Chem. 18, 215 [1983].? Chem. 3er. 98, 3025 [1965],· Liebigs Ana. Chem. 637, 135 [I960]).

Formula (IV) provides a general definition of the iso (thio) cyanates furthermore required as starting materials for carrying out process (b) according to the invention. In this formula (IV), R2 and Z preferably represent those radicals which have already been men10 tioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

The Iso (thio) cyanates of the formula (IV) are, for the most part, known compounds of organic chemistry. The IS compounds 2,2,2-trifluoroisopropyl cyanate and 2,2,2fcri£luoro-l, 1-dimethylethyl cyanate ere still unkncmn, but can be prepared according to known methods. Thus, iso (thio) cyanates are obtained, for example, if the corresponding amines are- reacted with phosgene, if appropriate in the presence of a base such as, for example, triethylamine (compare, for example, Dl-OS (German Published Specification) 2,304,082, D3-0S (German Published Specification) 2,512,514, uS Fatent 3,584,028, W Patent 3,311,654, G® 50/29599, Synthesis 1985, page 682 or J. Am. Chem. Soc. 77 1901-1902 (1955)?.

Formula (V) provides' a general definition of the trlascdlnone® required as starting materials for carrying out process (c) according fco the invention. In this formula (V) St1, X and Z preferably represent those radl30 cals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I> according to the Invention.

The triazolinonss of the forsmla (V) are known in scene cases (compare, for example, Heterocycl. Chem. 17, 1691-1696 (1980]).

Still unknown and likewise the subject of the present application are triaseoliaone® of the formula (Va) R1_aK-N^NHo Il I 21 5 YsOQ-FP (Va) in which a**1 represents straight-chain ox branched alkyl having to 4, In particular having X to 3, cartoon atoms, particularly preferably methyl and &5, X and X have the abovementioned meaning.

They are obtained analogously to the preparation of the known compounds of the formula (V) when ΧΞ-triarolinoaes of the formula (Ilia) ’‘'’ΤΡ Η (Ills) in which a’·-' and £ have the abovementioned meaning, are reacted with (thio)chloroformstes of the formula (IX) S?5-O-C~C1 <1X5 fl Y in which 38s and Ϋ have the abovementioned meaning, if appropriate is, the presence of & diluent such as, for example, fcefcrahydrofuraa and if appropriate la the presence o£ a reaction auxiliary such as, for example, potassium t-butoxide or sodium hydride, at temperatures between - 20eC and + 40°C (compare also the preparation examples).

The IH-triazolinones of the formula (Ilia) are known or obtainable analogously to known processes (compare, for example, J. Eeterocycl. Cheat. 16, 403 [1979],; J. Heterocycl- Cheat. 17, 1S91 [1980]; Surop. J. Med. Cheat. 18, 215 ¢1983] ; Chem. Ber. 98, 3025 [1965] ? Liebigs Ann. Cheat. 637, 135 [1960]).

Suitable acids for carrying out process (a) according to the invention are all inorganic and organic acids which can customarily be used for hydrazone cleavages. Preferably, inorganic mineral acids such as hydrochloric acid, sulphuric acid or phosphoric aeid are used.

Suitable diluents for carrying out process (a) according to the invention are all customary organic or inorganic solvents. Preferably, polar water-miscible organic solvents, in particular alcohols, such as methanol, ethanol, propanol or butanol, or mixtures thereof with water or pure water are used as diluents When carrying out process (a) according fc© the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 20°C and ISCPC, preferably at temperatures between 50°C and 120°C.

Process (a) according to the invention is customarily carried out at normal pressure or under reduced pressure. If the process is carried out under reduced pressure, pressure ranges between 20 and 400 mbar, preferably between 100 and 20® mbar, are suitable.

To carry out process according t© the invention, 1 to SO sel, preferably I to 20 m©l, of acid are in general - 29 employed per mole of hydrazone of the formula (II) . In this process, the hydrazone of the formula (II) is dissolved in a suitable amount of diluent, the required, amount of acid is then added and the mixture is slowly concentrated under reduced pressure over the course of several hours.

In a preferred embodiment, it is aliso possible to carry out process (a) according to the invention and the preparation of the precursors of the formula ¢11) neces10 sary fox- this process ia one reaction step in a so-called one-pot process.

There is the possibility here of selecting the trxazolinones of th© formula ¢2) a® starting compounds and reacting these successively in the one-pot process with amines of the formula (VI) and then with acid according to process (a) according to the invention (compare, for this purpose# also the preparation examples J or alfcersatively of selecting the triasoliaone hydrazones ©£ tha formula (VIII) as starting compounds and reacting these successively in the ©ae-pofc process with (thio)chloroformates of the formula (1X5 , then with amines of the formula (VI) and then with acid according to process (a) according to the invention.

Suitable diluents for carrying out process (b) according IS to the invention are all inert organic solvents. These include# ia particular# aliphatic# alicyclle or aromatic# optionally halogenated hydrocarbons# such as# for example, bensIne# benzene# toluene# xylene# chlorobenseae, petroleum ether# hexane# cyclohexane,» dlehloraaethane# chloroform# carbon tetrachloride, ethers# such as diethyl ether# dioxane# tetrahydrofiurar, ethylene glycol dimethyl ether or ethylene glycol diethyl ether# nitriles, each as acetonitrile or propionitrlle# amides# such as dimethylforsaaaide, dimethylacetamide, K-aethylforsaaailide, Si35 me thy Ipyrrol Idone sr hexamefchylphosphoraaide, or esters, such as ethyl acetate.

Process (b) according to the invention ia optionally carried out in the presence of a suitable reaction auxiliary. Those suitable are all customary inorganic or organic bases. These include, for example, tertiary amines, such ae triethylamine, N,N-dimefhylaniline, N,K-die thy lbenzylamine, Ν,Ν-dimethylcyclohexylamiae or dibutyltin dilaureate, pyridine, N,N-dimethyl&minopyridiae, diassahicyciooctaae (DA3CO) , di a sabi cyclononene (DHN) or diazabicycloundecene (DBu).

When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0**C and 150 °C, preferably at temperatures between 20°C and 100°C.

To carry out process ib) according to the invention, 1.0 to 2.0 mol, preferably 1.0 to 1.5 mol, of iso (thio)cyanate of the formula (IV) and optionally 0.001 to 2.0 mol, preferably 0.001 to 1.0 mol, of reaction auxiliary are Is general employed per mole of ΙΞ-triazoX20 iaone of the formula (III) .

The reaction is carried out and worked up and the reaction products are Isolated according to generally customary methods.

Suitable diluents for carrying out process Cc) according 2S to the invention are all Inert organic solvents. These include, In particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofur,an, ethylene glycol dimethyl ether or ethylene glycol diethyl ether, nitriles, such as acetonitrile or propionitrile, amides, such as dimethylformamide, dimethylacetamide, JSi-methylformanilide, H35 methylpyrrolldone cr hexamethylphosphorard.de, or esters, such as ethyl acetate, os sulphoxides, such as dimethyl sulphoxide.

Process (c) according to th© invention can optionally be carried out ia the presence of a suitable reaction auxiliary. Those which are suitable ar© all customary inorganic or organic bases. These include, for example, alkali metal hydroxides,· such as sodium hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate, as well as tertiary amines, such as triethylamine, Μ,Εϊ-dime thyl anil in©, pyridine, N, Si-dime thyl aminopyridine, diasabicyclooctane (DA3C0), diasabicycloaonene (D3K) or diazabicycloundecea,© (D3u) .

When carrying out process (c) according to the invention the reaction temperatures can be varied within a substantial range. In general; the process is carried out at temperatures between O’C and 120°C, preferably at temperatures between 20®C and 500C.

'To carry out process (c) according to the invention, 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of ajaine ©£ the formula (VI) and optionally 1.0 to 2.0 mol, preferably 1.0 to 1.2 mol, of reaction auxiliary are in general employed per mole of triazolinone of the formula .

The reaction is carried out and worked up and the reaction products are isolated according to generally customary methods.

In a particular embodiment it is also possible fc© carry out process (e> according to the invention and the preparation of the precursors of the fontnla (V) necessary for this in one reaction step in a so-called one-pot process.

IB-triazolinones of the formula (III) are used as starting materials here and these are reacted successively in the one-pot process first with (thio)chloroformates of the formula (ΙΣ) and then with amines of the formula (VI) invention. as in process (c) according to the Another method of obtaining compounds of the formula (I) according to the invention consists in reacting oxadirolinones of the formula (XI) (XI ) in which R1, R3 and y have the ahovenientioned meaning, with hydrazine hydrate in the presence of a suitable diluent such as, for example, methanol or ethanol, at temperatures between 20°C and 10O"C and thermally cyclising the carbaside acid derivatives of the formula (211) T=C-MH-R2 in which R1, 3a and y have the abovemeatioued meaning, thus obtainable in the presence of a suitable diluent IS such as, for example, toluene, chlorobenzene or dichlorobenzene, at temperatures between 90°C aad 200 **C.

Oxadiazolinones of the formula (ZI) are known (compare, for example, FR 1,415,SOS aad C.A. 64 s P5105g and also NX. S,510,645 and C.A. S5: F2274d-f) or obtainable accord20 ing to generally known processes, for example by reaction of the corresponding 4H-oxadiazolinones with iso (thio) cyanates of the formula (XV) analogously to carrying out process (b) according to the Invention or for the synthesis of the precursors of the forrxula (XX> .

The purification of th© final products of the formula (I) ie carried out with the aid of cueternary processes, for example by column chromatography or by recrystallization. Characterization is carried out with the aid of the melting point ox* with the aid of the proton nuclear magnetic resonance spectrum in the case of non-crystallizing compounds.

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants 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 undesired. 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: Dicotyledon weeds of the generas Sinapis, Bepidium, Galium, Stellaria, Matricaria, Amthesais, Galinsoga, Chenopodiusa, Hrtica, Senecio, Amaranthus, Porfulaca, Xanthium, Convolvulus, Ipomoea, Bolygonum, Sesbania, Ambrosia, Cirsium, Carduus, Soachus, Solanoa, Rorippa, Rotala, Linderaia, Bamiusa, Veronica, Abufciloa, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Mercurialis.

Dicotyledon cultures of the qaaera; ©ossypiusa, Glycine, Beta, Daucus, Phaseolus, Pieua, Solanua, Biausa, Zposaoea, Vicia, KFicofciaaa, Bycopersicon, Arachis, Brassica, Baceuca, Cucumis and Cucurbita.

Monocotyledon weeds of_fche generas Schiaochloa, Sefcaria, Ranicusa, Digitaria, Rhleua, Boa, Pesfeaca, Eleusisae, Brachiaria, Bolivia, Broaaus, Aveaaa, Cyperus, Sorghum, Agropyrca, Cynodoa, Konochoria, Fiauferistylis, Sagittaria, Eleocharis, Scirpus, P&spalum, Ischaemum, Sphenoclea, Dactyloctenxum, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera; Qry&a, Sea, Triticum, Bordeum, 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 concentre10 tion, for the total combating 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 combating weeds in perennial cultures, 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, and for the selective combating of weeds In annual cultures.

In this way the active compounds according fco the invention can be used with particularly good effect for combating monocotyledon and dicotyledon weeds, In particular in dicotyledon cultures, such as for example sugar beet.

In particular, the outstanding activity against mercury (Mercurialls), a problem weed which Is difficult to combat. Is worthy of mention.

The active compounds can be converted to the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates^ natural and synthetic materials impregnated with active compound, and very fins capsules in polymeric substances.

These formulations are produced in known maxmer, for example by mixing the active compounds with extenders, that Is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents .and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main; aromatics, such as xylene, toluene or alkyInaphthaleaes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chioroethylenes 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 dimethyl formamide and dimethyl sulphoxide, as well as wafer.

As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quarts, attapulgite, aacnfssorl I Ionite ©r diatomaceous earth, and ground synthetic minerals, such as highly disperse silicic acid, alumina and silicates, as solid carriers for granules there are suitable: for example crushed, and fractionated natural minerals such as calcifce, marble, pumice, sepiollte and dolomite, as well as synthetic granules ef inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, jaaise cobs and tobacco stalks> as emulsifying aad/or foam-forming agents there are suitable: for example noa-Ionic and anionic emulsifiers, such. as polyoxyethylene-fatty acid esters. - 36 ethylene-fatty alcohol ethers# for example alkylaryl polyglycol etherse alkylsulphonates# alkylsulphates# aryl sulphonates as well ss albumin hydrolysation products? as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders# granules or lafcices# such as gua arable# 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.

Xt 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# as© dyestuffs and metal phthalocyaaiae dyestuffs# 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%.

The active compounds according to the invention# as such or in the form of their formulations, ean also be used, for combating weeds# as mixtures with known herbicides# finished formulations or tank mixes being possible.

Herbicides which are suitable for the mixtures are knows herbicides such as# for example# l-amino-S-etayltb.Io-3(2,2-dimethylpropyl) -l,3,5-fcriaaine-2,4(ia,3S> -diene or N- <2-beassofchiaaolyl) -Μ,Ν* -diaaetSsyluxea for combating weeds in cereals; 4-amino-3-aetbyl-6-phenyl-l#2#4triazia-5 <4E)-one for combating weeds in sugar beet and 4-aadao-S- <1# l-diaefclaylefchcyl) -3-aethyIthi©-J#2#4"frIazIs5(4H)-one for combating weeds la soya beans. Mixtures with 5- (2-ehlor©-4"trifluoromethyl-phenoxy) -2-nitrobenzoic acid,- chloroacetyl-N- (methoxymethyl) -2,6-diethylanilide; methyl 6, 6-dimethyl"2,4-dioxo-3-[1-(2-propenyloxyamiao)-butylidene)-cyclohexanecarboxylic acid; methyl -(2,4-dichlorophenoxy)-2-aitrobenzoate; 5 - -amino-4chloro-2-pheayl-2,3-dihydro-3-oxy-pyridaziae; ethyl 2-{ ( (4-chloro-S-msfchoxy~2-pyrimidiayl) -aminocarbonyl) amiaosulphoayl}-benzoate; exo-X-methyl-4- (1-methylethyl) 2- (2-methylphenyl-methoxy) -7-oxabicyclo<2,2,1) -heptane; ethyl 2-{ [ (4-chloro-6-methoxy-2-pyrxdinyl)-aminocarbonyl) -aminosulphoayl}-benzoate; 3,6-dichloro-2pyridinecarboxylic acid; Sf,S-diethyl-N-cyclohexyl-thiocarbamate; 3- (methoxycarbonylaminophenyl) -N-phenyl carbamate; 2- [4- (2,4-dichlorophenoxy) -phenoxy] -propionic acid, Its methyl or Its ethyl ester; 4-amino-6-t-butyl-3efchylfchio-l,2,4-triazia-5 (4Ξ) -one? 2-{4~ (<6-chloro-2bensoxasolyl) -oxy) -phenoxy}-propanoic acid, its methyl or its ethyl ester; trlmethylsilylmsthyl 2-(4-{3,5-dlchloropyrid-2-yloxy) -phenoxy) -propionate; 5- (2-chloro-4-tri20 fluoroeaethy Iphenoxy) ~N-methyIsulphonyl-2-nitroheuzsrd.de; 2-{-4- [ (3-chloro~5- (trifluoromethyl) -2-pyridinyl) -oxy] phenoxy}-propanoic acid or its ethyl ester; methyl 2-(4(2,4-dichlorophenoxy) -phenoxy) -propionate; 2= (S-saethyl-S{l-methylethyl) -4-oxo-2-imidazolin-2-yl) -3-quinoline25 carboxylic acid; l-isobutylamiaocarboayl-2-isaxdasolidiaoae; 3-cyclohexyl-5,6-frimethylene-uracil; N-raethyl-2(1,3-beasothiasol-2-yloxy)-acetanilide; 2-chloro-N- (2,6dimethylphenyl) -N- ((IS) -pyrazol-l-yl-methyl) -acetamide; 2-ethyl-6-methyl-N- (1-methyl-2-methoxyethyl) -ehloroacef30 anilide; 3- (ethoxycarboaylaminophenyl) -N- <3* - methylphenyl) -carbamate; 2- (1- (ethoxamino) -bufcylidene) -5- (2ethylthiopropyl) -1,3-cyelohexadioae; N,K-dlis©proyl-S<2,3,3-trichloroallyl)-thiocarbamate or 2, S-diaitro-4fcrifluoromethyl-Ν,Ν-dipropylaniline ere also possible.

Surprisingly, some mixtures also show synergistic action.

Mixtures with other known active ©expounds, such as fungicides, insecticides, acaricides, aeaaaticides, bird repellents, plant nutrients and agents which I^rove 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 relatively wide range.· It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 10 kg of active compound per hectare of soil surface, preferably between 0.05 and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

Preparation Examples: Example. 1 H-aC^ Π NN •n^nh2 rk) 0 NH-CH2"CH(CH3)2 (Process a) ml of concentrated hydrochloric acid are added to 5 11.1 g (0-04 sool) of 1- (N-isobutvicarbaaaoyl) -4-isopropylideneimino-3-methyl-l,2,4-triazolin-5-one ia 100 ml of ethanol and the solution is concentrated at SO °C and about 200 mbar in the course of 5 hours oa a rotary evaporator. The residue is brought to crystallization by trituration with ethanoi/diethyl ether (1:1) and dried in air. 4.3 g ¢50% of theory) of 4-amino** 1 - (M-isobutylcarbamoyl)-3 -methyl-triazoXin.-5-one of melting point 183°C are obtained.

Example 2 3Ti I ^H3 0-C-NH—C—CH3 ^ch3 .

(Process b) 3.S g (0.036 mol) of t-butyl isocyanate and 0.05 g to 0.1 g of diazabicyclouadeceae Ο3Π) are added to 3.42 g (0.03 sol) of 4-amino-3-aethyl-l»2,4-(IE)-ftriaz©lia-S-one in 80 al of absolute acetonitrile, the mixture is stirred at 20°C for 2 hours and concentrated in vacuo, the residue is taken up in dichlorosethane, the solution is washed with water, dried over sodium, sulphate and concentrated in vast,© and the residue is crystallized by trituration with diethyl ether40 .0 g (78.3 % of theory) of 4-ajnino-l-(N-t-butylcarbamoyl)-3-aethyX~l(,2i,4-triazolln-5-one of melting point 132°C are obtained.

Example 3 (Process a - one-pot variant) 4.2 g (0.03 mol) of (2,2-dichlorocyclopropyl)methylamin® are added to 8.2 g (0.03 mol) of 4-isopropylideaeisnino-3methyl-l-phenoxycarbonyl-l, 2,4-triazolam-5-on© In 50 al of absolute tetrahydrofuran, the mixture is stirred at ®C for 12 hours and concentrated In vacuo, the residue is taken up in 100 ml of ethanol, 3 ml of concentrated hydrochloric acid are added and it is stirred at S0°C and 200 mbar for 3 to 4 hours. For working up, it is concentrated In vacuo, the residue is taken up in dichloromethane, and th® solution is washed three times with saturated aqueous sodium hydrogen carbonate solution, dried over sodium sulphate and concentrated is vacuo. The residue Is brought to crystallization by trituration with diethyl ether. 4.4 g (52 % of theory) of 4-amino-1- [N- (2,2-di chlorocyclopropy lmethy 1) carbambcyl] -3-methyl-I,2,4-triazolia-5one of melting point 149°C are obtained.

Example-4 O«C-NH-C-2)2~CH3 ch3 (Process ©) 8.9 g (0.088 mol) of 1,1- dime thy lbuty lamine are added to 3.2 g (0.0137 mol) of 4-amino-3-m©thyl"l-pheaoxycarboayll,2,4-triazolia-5-oae ia a mixture of 25 ml of tefcrahydrofuran and 10 ml of dioxane, the mixture Is heated at reflux temperature for 24 hours and concentrated in vacuo, the residue is taken up In dichloromethane, the solution is washed with two per cent sodium hydroxide solution and water and dried over sodium sulphate, the solvent is removed ia vacuo -and the residue crystallized hy trituration with diethyl ether. 1.9 g (61 % of theory) of 4-amiao-l-[N-(1,1-dimethylbutyl) -carbamoyl] -3-methyl-1,2,4-trlazolia-S-one of melting point 110°C are obtained.

The following substituted triazolinones of the general formula (I) II I 2 (I) NH-??2 are obtained in a corresponding manner and according to the general Instructions for the preparation: Table I Examnle R1 ΜΌ.

R5 Ca,3 R configuration X y Physical properties ‘R-HMR’’ Ο © 1.5 (d) G CS3 Ο O 1.5 (d) rS configuration '7 M.p. 13Sae Example R1 NoRs X Y Physical properties 0 M.p. 161°C 9 CHj -CH(CHs), G o M.p. 63°C 10 - (CB2)3-CB2C1 0 G 1.45 (m,4E) 11 cb3 -ch~c2m5 CK3 0 O 0.95 (t,,3E) 5 12 ch3 -ch2£7> 0 O M.p. 133°C 13 CH3 -CE(C2E5>2 0 O M.p. 103°C 14 Ca3 ~CH-CH{CH3)2 ch3 G G M.p. 103°C 15 C a ch3 0 0 M.p. 105°C 16 ch3 -ch2-ch2-/V> 0 O M.p. 135°C 10 17 ch3 CH, 1 3 o O M.p. 106eC (dec.) ~ch2-c-ch3 CH18 CB, Ca-, ch3 CH-(CH2)2 ch3 CH, I 3 -c-ch, J J CH, ~«CB23S-CH2CI Ο O 1.5496 S O M.p. Ι28θϋ S 0 M.p. 100 °C Ο O M.p. 131 °C Z ¥ Physical properties Example R1 No.

R2 CS3 Ο O M.p. 153°C Cs, CH3 CE3 CH, CH, I 3 -C-CH,C1 I ch3 -CH,-CH»CH0 ll ch2-c»oc2h5 r»w CH,C1 I ~ -C-CB, I * ca2ci CH, I , -c-chci2 O 0 M.p. 118°C O M.p. 92°C O M.p. 127°C 00¾2 1.5055 O M.p. 176°C CH28 C2«s CH 01½ EJMR’’: 4.4; 7.,95 CH3 C3Hs -CH,-C-CH, ' I " ch3 ch2f -C-CH, ! CH,F CH,F I " -C-CH, I 3 ch2f CKg I x=^ CH, O 0 M.p. 133°C Ο O M.p. 3040°C 0 *0.ΝΒ3’’: 4.36; 8.23 CH3 Sr Physical properties CH, I 3 C" C,H:~ I 0 M.p. 99°C ch3 33 . (> - CH- (CH2)3-CH(Cn3)2 0 0 S 4.40? 7 . SI 34 ch3 KZ)~^F3 0 0 M.p. 162°C 35 ch3 -ch2-(_) 0 o M.p. 198°C 5 3S CTmT U""3 -(fw ΐ -ΓΠ 0 0 M.p. 108109 °C 37 Vtf'cJoae^j G»ieueg 0 0 M.p. 168- 170 °C *2 O _ Ϊ «-P'W 0 0 M.p. 134136 °C 5,(3 ch3 ch, 1 0 0 M.p. 149°C 1 -CH—~C~CH, | j □ c:-:3 ch3 40 ch3 CH', 1 3 -C-C?3 0 0 M.p. 149- Tl ΕζΤΙ Off* Λ taS A W ch3 10 41 ch3 'KZl 0 0 M.p. 9394 °C 42 —CH, - CH*·» ~ CM «1« 0 F>i ''W’’ M *% Tl „ 17 8 °C 43 cs3 " CH,-CH- ί CH, Ϊ -,- CH-, | & «3 C-H- u2n3 0 0 M Η Q1 « A Λ D faff (t) «J lAi 92 ’G 44 a*.j 't*** £=*)?" I 3 0 o M.p. 102- 10319 C " V"^'2'fs5 ύηι ® (» «*s Example R1 R3 Bo..

Z T Physical properties si T "2 / 49 Ο O M.©« 178°C Ο H.a. 113eC O M.n. 1Q9°C O M.p. X48°C 0.35-0.6? 0.93 O © M.o. 175· (Hi A *» « "SU 1»c ;7 6> «ι (ϊ j*a«p,Al— .j e&e, U· chlorideS a ,n m « ie,1?»p W W ft,«B ® top a »«ϋ·ί·'ιώ Nw Ai Μη ΤΙβΕ,^Γ·1 α>λ ® 9*P ® ww W’*»» Λ® « ΥΛ3 I .CH,-C-CH,-N< CHCH" M.p. 198 ®C (hydrochloride) CH, ch3 IMF <« jjg·1 n 135 ®C C-CH=C< Cl Cl CH, M.p. 200· (Π) *& Φ !<*) t& W oi' %a Exaaaole No. R1 sa X T Physical properties 57 CH3 CH-a 1 J 0 o M.p. 119°C 1 -C-C^CH 1 ch3 58 CH, =CH-CH-»-Cl j 0 0 M.p. 136’C ch3 59 ch3 ch3 ch3 0 0 M.p. 122°C "C"CH7"C~CH, 1 2 1 3 CHg CH3 60 -CH-CF, 1 3 0 0 M.p. 141°C CBg 61 ch3 CHg 0 0 M.p. 176’C »c~cn I CHg 62 Ca3 -ck~2j4-ch3 0 0 M.p. 67’C CHg S3 0¾ -CH-CHg-OCHg 0 0 M.p. 120’C CKg 64 CHS -(csj2-oes, 0 0 M.p. 114°C 65 CHj c2hs -CH-CH^-nC 1 ~ C2H5 ch3 0 0 M.p. 84’C (hydrochloride) 66 ea. -CCHsJs-CHj, 0 s M.p. 147°C 67 0¾ -raz-VJ» 0 s M.p. 195’C 68 es. ~c2k5 0 s M.p. 205°C 6® cn, CH, 0 s M.p. 212®C 70 cs, -CH-/ S 0 0 M.p. 13®oe Example R1 No.

Ra CEtj CH3 CH3 CHj 75 CH3 •CH·—CH-C1 I I ch3 ch3 -CH-CH=C< CH-CH< Cl CX ,CH2C1 CH=CHCH-C-CH-CK«C ( ch3 ch3 CX Cl CH3 Ca3 CH3 -CZ3 80 CH3 ch2ci "CHC and Ca2CX "CK2-CH-CZ-j2CX I Cl (3:1) -CH~CH,C1 I c2h5 -ch-ch2-/ ch3 ch3 I ~C"CCH2)3-CH3 ch3 -CH~(CH2>s-CH3 CHCHPhysical properties M.p. 1X4°C 1.5328 M.p. 120eC a"° 1.3840 M.p. 158®C M.p. 2.47 eC a£2 1.4995 Hydrochloride j42 1.4991 1.492G M.p. 140eC ch-ch2-c»ch3 CHCH-ch2-ch< c9h © O K-p- 115*0 2rjS - 48 Example R1 No.

CH3 CH, 91 CH, Γ ηΊ ch3 H3C-^\X^CH3 •CH2C?2 Cl 0 0 0 O O O O A CJ n A Mfc»· -w Physical properties M.p. 134°C M.p. 164°C >*β » Η*? M.p 12X°C * C A 'V if», 2.33 M.p. 152°C M.p. 178°C Κ®pΊ 56 °C M *E) ·Ρ Λ'Λ 9 far 9 mm 49 / M.p. 113°C μ —, n *a %«» M.p. 98®C Example R1 No.

CRj CSj CEj CH3 CSj 100 CH3 101 C"3 102 CEEg 103 CH, 104 CH3 105 CS3 106 (¾ 107 0¾ R ifY -CHch2-cH"C2h3 CBg -ICH2l2-\ / CHCH-C-CH< I CH3 ch3 "CH-fCH2>2~CH3 ° ° ch3 G^Hc I2 »c~c2h5 c2h5 -CH-iCH2)2-CH< CHg O O Physical properties M.p. 210°C M.p. 175°C M.p. 106°C M.p. 104°C M.p. 120°C (dec.) M.p. I08eC M.p. 151°C M.p. 151°C M.p. 134°C M.p. 128®C «.p„ 101®C M.p. 73*C CH* CH, - 50 Example R1 Bq .

X 108 109 110 n: 112 115 116 117 118 119 Cx ca3 Λβξ,Κ’ββ CH, CH· '&A«£ Cx fAW "(ch2)3-n ( c2h5c2«5 2>3"N< ch3 CH, «3 CH-CH^-CN I 2 CW w 2-5 -ch-ch,-ch-c,h~ I I - ’ c2h5 ch3 -ch-ch,-ch< CHCH" CHC,H 2"S CH-(CH2)3~N< ·' I 'C2KS CH, -CH-CH,-N< CH, CHy CKΛ1Ί *0 Xx ’2 "5 >-Cn3 X r* Xw25 Physical properties „a0 ι SBIS (hydrochloride) M.p. 210°C (hydrochloride) Ο 0 M.p. 145°C 1-4890 O 2¾° 1-48S8 Ο O M.p. 108°c (hydrochloride) O M.p. 81eC Ο O ag® 1.5100 (hydro©ride) fiHh 1.5150 (hydrochloride) M.p. 157°S O M.p. 116°C Ο O M.p. 145°C w ·*% n 1 a, 0 a έκΰ» W 120 Example RA Ko. 121 122 ~ CH2CH2"CC 2Hg 123 2i Tw»&, 126 127 CH. 123 «Β9Α 2« 130 131 X32 CH, ,33 CEL z 4b Physical properties 0 o M.p. 123°C 0 0 Μ Ώ 0 1 2 ° Γ 0 0 M.p. 93°C 0 o M.p. 93°C 0 0 AAA u> 1.58 (dd) f> 1.77 (t)j 2.76 (t) 0 o M.p. 142°C 0 © M.p. 123°C (esxdo - form) 0 0 M.p. 131®C (ex©-form) 0 o M H *31 a p1 λ-α a ® Oto «Ρ *2 Aw ·*£·' o Μ n 1 Ο ς ® O «.'« « Ibj3 n aite aw 0 © M r» 11 7 ° Γ »,« m ® aSta ab> 3 Wa» Hi © ’•tm „ we; " >. 1.45 (s)y 7.04-7.43 (n) 0 0 M.p. 1SS®C © © M ¥·, "8 "?l gs «,fJ tttnh Φ W1 Φ 134 Example R1 No.

R2 X ¥ Physical properties 135 CHj CH, 1 -CH-C-CH, 1 1 3C2H5 CH3 0 0 M.p. 157°C 136 ch3 'p „ -^-UO1CH3 0 0 M.p'. 180°C 137 CEj - C H 2 -1H 2—^~^>~C 1 0 o M.p. 188°C 138 cn3 -CH-Z ^-<2H5 CH- O 0 M.p. 95°C The ^H-NMR spectra were recorded in deuterochloroform CCDC1S) using t e trams thylsIlane (TMS) as the internal s taad&rd. The chemical shift Is given as the δ value ia ppm.

Preparation of the starting ccsmpounds Example XI-1 >:h3 k CH, n^X. 0 NH-CH2"CH(CH3)2 g (0.12 mol) of isobutyl Isocyanate are added dropwise at 20*C with stirring to 6 g (0.04 mol) of 4isoprcspylideaeimiao-S-aiethyl-lH-triazolia-S-oae and 4 g (0,.04 mol) of triethylamine ia 20 ml of dioxane and the mixture Is stirred for 3 hours at 100°C after completion of the addition. For working up, th® reaction mixture Is concentrated in vacuo, the residue is taken up In 100 al of dichloromethane, and the solution Is washed several times with 100 ati of water In each case, dried over sodium sulphate and freed from solvent la vacuo. 11.,2 g (100% of theory) of 1- (N-lsdbutylcarbamoyl> 53 - isopropylidaneimino- 3 -methyl -1,2,4- triazolin- 5 -one are obtained as an oil^-NMR (CDC13) : δ - 0.85 (d, 6H) ppm.

The following precursors of the general formula ill) ? ίΝΨ(II ) ''nh-r2 are obtained ia a corresponding manner and according to the general instructions for the preparations Table 2 Ex- ample No. a- Ra -C s 2 Physical properties ΧΣ-2 -G> «C(CH3>2 © 0 M.p. 125°C ΪΪ-3 CS3 <Ξ> =CS-CS(CS3> a 0 O "H-NMR*’ s 3.9 II-4 CS3 -ch-c2h5 =e(oy 2 0 0 M.p. 87®C ch3 II-5 ce3 -CS(CS3)2 =C(CSs)a 0 O M.p. 107eC XI-S cs3 -cs(c2s552 =C(CS3)2 0 0 M.p. S3SC 11-7 Ca, -cs- CHiCS3). «eccsy. 0 0XS-NH£O : 0.54 (d, c«3S XI-8 ch3 -CH2-/V> ^eccEy 2 0 o M.p. 115®C IX-9 cs, 3 CHg 1 d -C(CH3)2 0 O M.p. 38°C ~CGH2C1 CHg 11-10 GH^ f- —< H ) »es © o M.p. 139*C ch3 Ex- ample No. Rx P2 ^R3 X y Physical properties XI-11 ch3c2H5 c2H5 «C (Ο&3) «* 0 o Oil 11-12 CHj -CHg-COOCsHs =C(C33)2 0 0 M.p. 108°C 11-13 cs3 -C3,~CH=C32 =C(CE3)2 0 o M.p. 86°C 11-14 ch3 CFg sC(CH3)2 0 0 M.p. 158°C Λ ? 11-15 11-16 CH, =C (03,)2 «C(CH3)3 0 H,p. 218°C 0 M.p.. 1S5°C 11-17 CH3 CH3 =C(CH3)2 I -ch2-c-ch3 ch3 O 0 K.©. 121 122®C Examo 1 e 111 -1 ^ch3 H,C\-— II I CHg 11.4 g (0.1 mol) of 4-a3nino-3-Eaefchyl-lH-triazolia-5-one (compare Biurop. J.Med. Chem.? Chin. ther. 18, 215-220 (1983]) and 0.1 g of p-toluenesulphonic acid ia 100 ml (79.06 g? 1.36 mol) of acetone are stirred at 70*C for 40 hours, and the mixture Is then concentrated ia vacuo. 15.4 g (100% of theory) of, 4-isopropylideneimino3-saeth.yl-lH-triazolia-5-oae of melting point I40-I44®C are obtained.

Example V-l 2.7 g (0.024 mol) of potassium t-butoxide are added to 2.3 eg (0.02 mol) of 4-asaino-3-methyl-l,2,4-(1H)triazolin-5-one in 25 ml os absolute fcefcrahydrofuraa, the mixture ie stirred for 1 hour at 20 eC, 3.1 g (0.02 mol) of phenyl chloroformate are then added dropwise with stirring, the mixture is stirred at room temperature for 12 hours, then adjusted to p35 with glacial acetic acid axxd concentrated in vacuo,» the residue is taken up in chloroform, the solution is washed with water, dried over sodiwa sulphate and concentrated in vacuo and the residue is crystallized by trituration with ether. 1.1 g (23.5% of theory) of 4-aaaino-3~jaethyl-lphenoxycarbo»yl-l,2,4-triazolia-5-©ae of melting point 175°C are obtained.

Sscaiaole 5E-1 13.4 g (0.12 mol) of potassium t-butoxide are initially added at room temperature to 15.4 g (0.1 mol) of 4-isoprcpylideneinin©-3-aaethyl-l,2,4-· (IE)-triazolia-5oae in 100 ml of absolute tetrahydrofuran and the mixture is stirred at room temperature for one hour, then 15.5 g (0.1 mol) of phenyl ehloroformat® are added and it is stirred at 20)°C for a further 12 hours.

For working up, it is acidified with glacial acetic acid and concentrated is vacuo, the residue is taker, up ia chloroform, the solution is washed with water, dried over sodium sulphate and concentrated in vacuo once again, and the residue I® recryatallized from acetone. g (36.5% of theory) of 4-isopropylideneimIno3-methyl-1-phenoxycarbonyl-1,2,4-triazolin-5-one of melting point 162‘C are obtained.

Bxamole Z-2 CH,>-N^=C < 3 II CH CH O=C-O-C2Hs 1.5 g (0.05 mol) of sodium hydride are added at 20°C to 7.7' g (0.05 mol) of 4-isopropylideneimino-3methyl-1,2,4-(1Ξ)-triasolin-5-one ia 50 ml of absolute tetrahydrofuran, the mixture Is stirred at room temperature for one hour, 5.4 g (0.05 mol) of ethyl chioroformate are then added dropwise with stirring and the mixture is stirred at 20°C for a further 12 hours after addition is complete.

For working up, it is acidified with glacial acetic acid and concentrated in vacuo, the residue is taken up la dichioromethane, the solution Is washed with water, dried over sodium sulphate and concentrated in vacuo once again and the residue Is recrystallised from isopropanol. .0 g (44% of theory) of 1-ethoxycarbonyl-420 isopropylideneimino-3-methyl-l,2,4-triazolin-5-one of melting point 91°C are obtained. yse....jSxamoles.:.

The compounds shown below were employed as comparison, substances In the following use examples: CA) 4-Aaiao-3-methyl-6-phenyl-1,2,4-triazin-5-one (known from DB-OS (German Published Specification) 2,364,474, Example 1-22) HN\/N- C -NH-CH (CH3) 2 (3) II o N- Xsobutyl - 2 «oximidazolidiae-I-carboxamide (known feoaa, Wegler Chemie der PfXanreaschuts- und Seh&dliagsbakjhnpfungKBiifcfcelB (Chemistry of Plant Protection Agents and Pesticides) Vol. 5, page 219 (1977)) Example,,,. A Pro-©mergence test Solvent: 5 parts by weight of acetone Bmulsifier: 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 concentration is diluted with water to th® desired coaceatratioha.

Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of so importance only the amount of active compound applied per unit area being decisive. After three ’weeks, the degree of damage to the plants As rated in % damage in comparison ft© the development of the untreated control. The figures denotes 0% « a© actios (like untreated control) 100% a total destruction la this test, for example, the ccss^ounds according to Preparation Examples 2, 14, 23, 32, 41, 45, 48 and 57 shew a distinctly better herbicidal action against weeds and also a distinctly better selectivity is crop plants such as, for exarple, sugar beet, than the comparison substance (3).

Example 3 Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate Is diluted with water to the desired concentration.

Test plants which have a height of 5 - 15 cm are sprayed with the preparation of the active compound in such a way as fco apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor I© so chosen that the particular amounts of active compound desired are applied In 2,000 1 of water/ha. After three weeks, the degree of damage to the plants Is rated la % damage In comparison to the development of the untreated control. The figures denote: 0% « so action (like untreated control) 100% « total destruction In this test, for example, the compounds according to Examples 1 and 48 .and also 1, 2, 3, 14, 23, 32, 41, 45, 48, 57 and 78 show a distinctly better herbicidal action than the cra^arisra substance (A) or (B) Is combating mono- and dicotyledon weds.

Claims (17)

1. Patent Claims Substituted triazolinones of the formula (I) N^NH 2 Y in which R 1 represents hydrogen, in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinvl having 2 to 8 carbon atoms, halogen ©alkyl having 1 fco 3 carbon atoms and 1 to 17 identical or different halogen atoms, halogemoalkenyl having 2 fco S carbon atoms and 1 to 15 identical or different halogen atoms, halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 Identical or different halogen atoms, alkoxyalkyl having 1 to S carbon stems in the individual alkyl moieties, cycloaikyi or cycloalkylalkyl In each case having 3 to 7 carbon atoms In the cycloaikyi moiety and optionally 1 to 6 carbon atoms la the straightchain ox branched alkyl moiety, aryl having 6 fco 10 carbon atoms In the aryl aoiefcy, which is monosubstituted or polysubstitufced by identical or different substituents, suitable, aryl substituents In each ease being: halogen, cyano, nitro and in each ease straightchain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogeaoalfcylthi© in each case having 1 fco 4 carbon atoms: and optionally 1 fco 9 Identical or different halogen atoms, R 2 represents hydrogen. In each case straight-chain or branched alkyl having 1 fc© 18 carbon afeoae, alkenyl SO having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 fco 8 carbon atoms aad 1 fco 17 identical or different halogen atoms, halcgeaoalkeayl or halogenoalkinyl in each ease having 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 0 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkvl or alkoxycarbonylalkenyl In each case having up to 6 carbon atoms in the individual alkyl or alkenyl moieties, alkylamiaoalkyl or dialkylamisoalkyl in each case having 1 to S carbon atoms in the individual alkyl moieties, eycloalkyl having 11 carbon atoms or eycloalkyl, cyeloalkylalkyl, cycloaXkenyl or cycloalkenylalkyl ia each ease having 3 to 8 carbon atoms la the eycloalkyl or eycloalkenyl moiety and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety. In each case optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents in each case being: halogen, cyano and in each case straight-chain or branched alkyl or halogenoalkyl in each case having 1 to 4 carbon atoms, and optionally X to 9 identical or different halogen atoms or straight-chain or branched halogenoalkenyl having up to 4 carbon atoms and 1 to 5 identical or different halogen atoms or in each case doubly linked alkanediyl or alkenediyl in each ease having up to 4 carbon atoms; R 2 additionally represents heterocyclylalkyl having 1 to 6 carbon atoms in the straight-chain ©r branched alkyl moiety and 1 to 9 carbon atoms and also 1 to 3 hetero atoms· - In particular nitrogen, oxygen and/or sulphur - in the heterocyclyl moiety .and which Is optionally sososubstltuted or polysubstituted ia the heterocyclyl moiety by Identical or different substituents, suitable substituents beings halogen, cyan©, nitro, and In each case straight-chain or branched alkyl, - 61 alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or alkoxycarbonyl in each case having 1 to 5 carbon atoms and optionally 1 to 9 identical or different halogen atoms? R 3 additionS ally represents in each case straight-chain or branched alkoxy having 1 to 8 carbon atoms# alkenyloxy having 2 to S carbon atoms or alkinyloxy having 2 to 3 carbon atoms and finally aralkyl# aroyl# aryl# aralkyloxy or aryloxy# In each case having 6 10 to 10 carbon atoms in the aryl moiety and optionally 1 to 8 carbon atoms in the alkyl moiety# and in each case optionally monosubstituted or polysubstituted by Identical or different substituents# suitable alkyl substituents optionally being halogen and 15 cyano and suitable aryl substituents in each case . beings halogen# cyan©# nitro# hydroxyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio# halogenoalkyl# halogenoalkoxy, halogenoalkylthio, alkylsulphiayl# alkylsulphonyl, halogenoalkyl20 sulphinyl,' halogenoalkylsulphonyl, alkanoyl or alkoxycarbonyl in each case having 1 to 6 carbon atoms la the alkyl moiety and optionally 1 to 9 identical or different halogen atoms, cycloalkyl having 3 to 6 carbon atoms and phenoxy, 25 Z represents oxygen or sulphur and 1' represents oxygen or sulphur.

2. Substituted triazollnones of the formula (I) according to Claim 1, characterized in that Br represents hydrogen, methyl# ethyl# a- or I-propyl# 30 η-, 1-# s- or t-butyl# n- or i-pentyl, st~ or x-hexyl, allyl# propargyl, straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen a teas, in particular fluorine, chlorine or bromine, methoxymethyl# ethoxyssefchyl, prcspoacymethyl, cyclopeatyl. cyclohexyl, cyclopropyl, cyclopropylmethyl, cyclohexylmethyl, cyclohexvlethyl, for phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents being: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, a- or I-propyl, a-, 1-, s- or t-butyl, methoxy, ethoxy, methylthio, fcrifluoromethyl, trlfiuoromefchoxy or trifluoromethylthio, B. represents hydrogen, methyl, ethyl, sa- or I-propyl, η-, I-, s- or t-butyl, In each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, allyl, ia each ease straight-chain or branched butenyl, penteayl or hexenyl, propargyl, in each ease straight-chain or branched butlnyl, pentiayl or heociayl, straight-chain or branched halogeaoalkyl having 1 to 8 carbon atoms and 1 to 9 identical or different halogen atoms, In particular fluorine, chlorine ©r bromine, in each case straight-chain or branched halogenoalkenyl or halogenoakynyl in each case having 3 to S carbon atoms and 1 to 3 halogen atoms, in particular fluorine or chlorine, In each case straight-chain or branched cyanoalkyl having 1 to S carbon atosas 1s, the alkyl moiety, hydroxyalkyl having l fco 6 carbon atoms and 1 to 3 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarboaylalkenyl, alkylamiaoalkyl or dialkylaminoalkyl In each case having up to 4 carbon atoms In the individual alkyl or alkenyl moieties ©r cyclopropyl, eye1opropyImethy1, cyclopropylefchyl, cyelopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclohexylmefchyl, eyelohexylethyl, cyclohexenyl or cyclohexd&ylaafchyl, In each case optionally monosubstltutad fco trlsubsfclfcutsd by identical ©r different substituents, suitable substituents la each ease being: fluorine, chlorine, bromine, methyl, ethyl, a- o>* 1-propyl, a-, I-, s- or t-butyl, cyano. methanediyl, ethaaediyl, butanediyl or butadisnediyl or dichloroallyl; R 2 furthermore represents heterocyclylmethyl, heterocyclylpropvl or heterocyclylethyl which are option5 ally monosubstitutsd to trisubstituted ia the heterocyclyl moiety by identical or different substituents,» suitable heterocycles la each case beings Z la each case representing oxygen or sulphur and 10 suitable substituents la each case being: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, a- or i-propyl, η-, I-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; 15 R 2 additionally represents in each ease straight-chain ©r branched alkoxy having 1 to € carbon, atoms, alkeayloxy having 3 to 6 carbon atoms or alkinyloxy having 3 to 6 carbon atoms or optionally straightchain or branched benzyl, phenylethyl, phenylpropvl, 20 phenylbutyl, pheaylpeafcyl, pheoyihexyl, phenylheptyl, phenylcyanomethyl, phenylcyaaoethyl, phenylcyanopropyl, benzyloxy, phenyl ethoxy, phenoxy, benzoyl, phenyl or naphthyl, in each ease optionally aoaosubstituted to trisubstituted by identical or 25 different substituents, suitable phenyl substituents in each case being: fluorine, chlorine, brcsaiae, hydroxyl, cyan©, nitro, methyl, ethyl, a- or i-propyl, η-, I-, s- or t-butyl, aethoxy, ethoxy, - 64 methylthio, trifluoromethyl, trifluoromethoxy, trifluorome thylthio, trifluorome thylsulphinyl, trifluoromethylsulphonyl, methylsulphinyl, methylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenoxy, X represents oxygen or sulphur and Ύ represents oxygen or sulphur.

3. Process for the preparation of substituted triazolinones of the formula (I) Il I in which R 1 represents hydrogen, in each case straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to © carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 3 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl having 2 to S carbon atoms and 1 to 15 identical or different halogen atoms, halogeaoalkiayl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen atons, alkozyalkyl having 1 to € carbon atoms is the individual alkyl moieties, cycloalkyl or cycloalkylalkyl in each case having 3 to 7 carbon atoms is the cycloalkyl moiety and optionally 1 to S carbon atoms ia the straightchain or branched alkyl moiety, aryl having 6 to 10 carbon atcms in the aryl moiety, 'which is aoaosuhstituted er polysubstituted by identical or different substituents, suitable aryl substituents in each ease being: halogen, cyano, nitro and in each ease straightchain or branched alkyl, alkoxy, alkylthio, h&logenoalkyl, halogenoalkoxy or halogenoalkylthio in each case having 1 to

4. Carbon atoms and optionally 1 to 9 identical or different halogen atoms, represents hydrogen, in each case straight-chain or branched alkyl having 1 to 18 carbon atoms,» alkenyl having 2 to 3 carbon atoms, alkinyl having 2 to 9 carbon atoms, halogeaoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogeaoalkinyl in each ease having 2 to 8 carbon atoms and 1 co 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 3 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl in each case having up fo 6 carbon atoms in the individual alkyl or alkenyl moieties, alkylaminoalkyl or dialkylasainoalkyl in each ease having 1 to 6 carbon atoms in the individual alkyl moieties, cycloalkvl having 11 carbon atoms or cycloalkyl, cycloalkylalkyl, cycloalkenyl or eyeloalkenylalkyl in each case having 3 . to Θ carbon atoms in the cycloalkyl or cycloalkenyl moiety and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, ia each case optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents in each case being: halogen, cyano and in each case straight-chain or branched alkyl cr halogeaoalkyl in each case having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms or straight-chain or branched faalogeaealkeayl having up to 4 carbon atoms .and 1 to S identical or different halogen, atoms or in each ease doubly linked alkanediyl or alkenediyl in each ease having up to 4 carbon stems? B s additionally represents hetero66 cyclylalkyl having 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and 1 to 9 carbon atoms and also 1 to 3 hetero atoms - in particular nitrogen, oxygen and/or sulphur - in the 5. Hefcerocyclyl moiety and which is optionally monosubstituted or polysubstituted ia the hefcerocyclyl moiety by Identical or different substituents, suitable substituents beings halogen, cyano, nitro, and ia each case straight-chain or branched alkyl, 10 alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogeaoalkylthio or alkoscyearhonyX In each case having 1 to 5 carbon atoms and optionally 1 to 9 identical or different halogen atomsR 3 additionally represents In each case straight-chain or IS branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to .3 carbon atoms and finally aralkyl, aroyl, aryl, aralkyloxy or aryloxy. Is. each case having 6 to 10 carbon atoms la the aryl aoiefcy and optionally 20 1 to 8 carbon atoms In the alkyl moiety, and In each ease optionally aoaosubstituted or polysubsfcituted by identical or different substituents, suitable alkyl substituents optionally being halogen and cyan© and suitable aryl substituents In each case 25 being: halogen, cyano, nitro, hydroxyl, In each ease straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogeaoalkoscy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkanoyl or 30 alkoxycarboavl in each case having X to 6 carbon atoms In the alkyl moiety and optionally 1 to 9 identical ©r different halogen atoms, cycloaikyi having 3 to 6 carbon atoms and phenoxy, X represents oxygen or sulphur and 35 T represents oxygen or sulphur, characterized in that (II ) - 57 a) hydrazones of th® formula (II) In which R 1 , R 2 , Z and, Y have the abovementioned meaning and a 3 and R* independently of one another in each case repre5 sent hydrogen, alkyl, aralkyl or aryl, are reacted with an acid. If appropriate In the presence of a diluent, or in that (b) Xa-triazolimones of the formula (III) (III) 10 in which R 1 and 2E have the abovementioned meaning, are reacted with iso (thio) cyanates of the formula (IV) (IV) In which B 2 and 1 have the abovementioned Meaning, if appropriate in th© presence of a diluent and if appropriate in the presence of a reaction auxiliary, or ia that (c) fcriazolinones of the formula (V) -N^HLX (V) y 0-R 5 5 in which R 1 , Si and T have the .abovenentioned meaning, and R 5 represents alkyl, aryl or arylalkyl, are reacted with amines of the formula (71) 10 R’-NHj (VI) in which S 2 has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate ia the presence of a reaction auxiliary. 1S 4. Herbicidal agents, characterised in that they contain at least on® substituted triazolinoae of the formula (1) according· to Claims 1 and 2.

5. Process for the control of weeds, characterised in that substituted fcriazolinones of the formula (I> 20 according to Claims 1 and 2 are allowed to act on the weeds and/or their environment.

6. Use of substituted triazolinones of the formula (I) according to Claims 1 and 2 for the control of weeds.

7. Process for the production o£ herbicidal agents# 5 characterized in that substituted triazolinonas of the formula (I) according to Claims 1 and 2 are mixed with extenders and/or surface-active substances. (II) Hydrazones of the formula

8. -Ν-Ή 1 '^x =c ^ , ΪΤ 1 (II) y ^ Cx ‘hh-r 2 in which

9. 10 R 1 represents hydrogen# In each branched alkyl having 1 to 8 having 2 t© 8 carbon atoms, carbon atoms, halogenoalkvl ease straight-chain or carbon atoms, alkenyl alkinyl having 2 to 8 having 1 to 8 carbon atoms and 1 to 17 Identical or different halogen 15 atoms, halogenoalkenyl having 2 to 8 carbon atoms and I to 15 Identical or different halogen atoms# halogenoalkinyl having 2 to 8 carbon atoms and 1 to 13 identical or different halogen a tens,,, alkoscyalkyl having 1 to 6 carbon atoms In the individual alkyl 20 moieties# cycloalkyl or cycloalkylalkyl in each case having 3 to 7 carbon atoms In the cycloalkyl moiety and optionally 1 to 6 carbon atoms in the straightchain or branched alkyl moiety# aryl having 6 to 10 carbon atoms in the aryl moiety# which is saoaosufosft25 ituted or polysubstituted by identical or different substituents, suitable aryl substituents in each case beings halogen) cyano# nitro and in each case ©traight70 chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl,, halogenoalkoxy or halogenoalkyl thio in each ease having 1 to 4 carbon atoms and optionally 1 to 9 identical or different halogen atoms, S 2 represents hydrogen, in each case straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 fco S carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl In each ease having 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 5 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl In each case having up to 6 carbon atoms in the Individual alkyl or alkenyl moieties, alkylaminoalkyl or dialkylaminoalkyl in each case having 1 to 6 carbon atoms In the individual alkyl moieties, eycloalkyl having 10. 11 carbon atoms or eycloalkyl, cycloalkvlalkyl, cycloalkenyl or cycloalkenylalkyl in each ease having 3 to «8 carbon atoms in the eycloalkyl or cycloalkenyl moiety and optionally 1 to 6 carbon atoms ia the straight-chain or branched alkyl moiety, in each case optionally monosubstituted or polysubstitufced by identical or different substituents, suitable substituents In each ease beings halogen, cyano and la each case straight-chain or branched alkyl or halogenoalkyl in each case having 1 to 4 carbon atoms and optionally 1 to 9 Identical or different halogen atoms or straight-chain or branched halogenoalkenyl having up to 4 carbon atoms and 1 fco 5 Identical or different halogen atoms or In each case doubly linked alkanediyl or alkenedlyl in each case having up to 4 carbon atoms; B 2 additionally represents heterocyclylalkyl having 1 to 6 carbon, atoms ia the straight-chain or branched alkyl moiety and 1 to 9 carbon atoms and also 1 to 3 hetero atoms - ia particular nitrogen, oxygen and/or sulphur - in the heterocyclyl moiety and which is optionally mono5 substituted or polysubstituted In the heterocyclyl moiety by identical or different substituents, suitable substituents being: halogen, cyano, nitro, and la each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, 10 halogenoalkylthio or alkoxycarbonyl In each case having 1 to 5 carbon atoms and optionally 1 to 9 Identical or different halogen atoms; R 2 additionally represents in each ease (Straight-chain or branched alkoxy having 1 to 3 carbon atoms, alkenyl15 oxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms: and finally aralkyl, aroyl, aryl, aralkyloxy or aryloxy, la each ease having 6 to 10 carbon atoms in the aryl moiety and optionally 1 to 8 carbon atoms la the alkyl moiety, and in each 20 case optionally monosubstituted or polysubstituted by Identical or different substituents, suitable alkyl substituents optionally being halogen and cyano and suitable aryl -substituents in each case being: halogen, cyano, nitro, hydroxyl, in each case 25 straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkylsulphlnyl, h&Xogenoalkylsulphoayl, alkanoyl or alkoxycarbonyl in each case having 1 to 6 carbon 30 atoms in the alkyl moiety and optionally 1 to 9 Identical or different halogen atoms, cycloalkyl having 3 to S carbon atoms and phenoxy, Z represents oxygen or sulphur, ¥ represents oxygen or sulphur arid 35 S 3 .and R* 1 Independently of one another In each case represent hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms or phenyl or benzyl, apart from the compound 1- (N-4-bromophenylthiocarbamoyl) -4-pheaylideneamino1,2,4“triazoline-5-thione. Triazolinones of the formula (Va) Y=C-O-R 5 in which R 1 ' 1 represents straight-chain or branched alkyl having 1 to 4 carbon atoms, X and ϊ independently of one another represent oxygen ©r sulphur, K s represents straight-chain or branched alkyl having 1 to 4 carbon atoms or phenyl or benzyl, optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents is each case being: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio in each case having 1 to 4 carbon atoms or is each ease straight-chain or branched halogenoalkyl, halogeaoalkoxy or halogenoalkylthio in each case having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms.

10. Triazolinoaes of the formula (Za> (3£s> Y=C-O-R 5 in which R 1 1 represents straight-chain or branched alkyl having 1 fo 4 carbon atoms, R 3 and R* independently of one another ia each case 5 represent hydrogen,, straight-chain or branched alkyl having 1 co 4 carbon atoms or phenyl or benzyl, R 5 represents straight-chain, or branched alkyl having 1 to 4 carbon atoms or phenyl or benzyl, optionally monosubstituted to trisubstituted by identical or 10 different substituents, suitable substituents in each case being: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio in each case having 1 to 4 carbon atoms or in each case straight-chain or branched halogenoalkyl, 15 halogenoalkoxy or halogenoalkylthio in each case having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, Z and Y independently of one another represent oxygen or sulphur. 20 11. a substituted triazolinone of the formula given and defined is Claim 1, substantia Ily as hereinbefore described with particular reference to the Examples 1-138 of the accompanying Examples.

11. 12. S, process for the preparation of a substituted 25 triazolinone of the formula (I) given and defined in Claim 1, substantially as hereinbefore described and exemplified. -7413. δ substituted triazolinone of the formula (X) given and defined in Claim 1, whenever prepared by a process claimed xn Claim 3; or 12.

12. 14. & herbicidal agent according to Claim 4, substantially as hereinbefore described with particular reference to Examples δ and B of the accompanying Examples.

13. 15. & method according to Claim 5 for combating weeds, substantially as hereinbefore described with particular reference to Examples A and B of the accompanying Examples.

14. 16. 0se according to Claim 6, substantially as hereinbefore described with particular reference to Examples & and B of the accompanying Examples.

15. 17. A hydrazone of the formula (IX) given and defined in Claim 8, substantially as hereinbefore described and exemplified.

16. 18. δ trlasollnone of the formula (Va) given and defined In Claim 9, substantially as hereinbefore described and exemplified.

17. 19. & triaxolinone of the formula (Xa) given and defined in Claim 10, substantially as hereinbefore described and exemplified.