MXPA01008399A - 1-aryl-1,3,5-triazine-4-thione-2,6-diones, production thereof and use thereof as herbicides - Google Patents

Abstract

The invention relates to novel 1-aryl-4-thiotriazines of formula (I), wherein R1=H, NH2, C1-C4-alkyl, C1-C4-alkyl halide;R2=H, NH2, C1-C4-alkyl, C1-C4-alkyl halide;R3=H, halogen;R4=CN, halogen;Y=nitrogen, the methine group or together with R5, a bridge>C-O-C(R6)=N-;R5=1) hydrogen, hydroxy, mercapto, nitro, halogen, C1-C6-alkyl, C1-C6-alkyl halide, 2) C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio, C2-C6-alkinyloxy or C2-C6-alkinylthio, each of these 8 radicals optionally bearing one of the following substituents:halogen, cyano, -CO-R8, -CO-OR8 or -CO-N(R8)-R9;3) -CO-R11, -C(R11)(OR13)(OR14), -C(R11)=C(R15)-CO-R16, -CH(R11)-CH(R15)-CO-R16, -CO-OR20, -C(R10)=N-OR7, -N(R21)-R22 or -CO-N(R21)-R22;and R6=H, halogen, optionally substituted C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkinyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy, C3-C6-cycloalkyl or C3-C6-cycloalkoxy. The invention also relates to salts and enol ethers of the inventive compounds (I), to a method for producing them and to their use as herbicides.

Description

l-ARIL-l, 3,5-TRIAZIN-4-TION-2, 6-DIONAS, THESE PRODUCTS AND THEIR USE AS HERBICIDES The present invention relates to the novel l-aryl-4-thiotriazines of the formula I: in which the variables have the following meanings: R 1 is hydrogen, amino, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl, R2 is hydrogen, amino, C1-C4 alkyl or C1-C4 haloalkyl R is hydrogen or halogen R4 is cyano or halogen And it's nitrogen, the methino group or, along with R, it's a bridge > C-0-C (R6) = N-1) hydrogen, hydroxyl, mercapto, nitro, halogen, C? -C6 alkyl, haloalkyl of C? -C6 2) Ci-Ce alkoxy, C 1 -C 6 alkylthio, C 3 -C 6 cycloalkoxy / C 3 -C 6 cycloalkylthio, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenylthio, C 2 -C 6 alkynyloxy or C 2 -C 6 alkynylthio , it being possible, if desired, that each of these eight radicals be linked to one of the following substituents: halogen, cyano, -CO-R8, -CO-OR8 or -C0-N (R8) -R9 3) -CO-R 11 -CtR, 1111) (OR 1i3J) N (OR, 14, -C (Rn) = C (R15) -CO-R16, -CH: Rn) -CH (R15) -CO-R 16 -CO-OR 2o -C (R10) = N-OR7, N (R .2i / 1), - R < "or -CO-N (R 21i), - R, 22 R is hydrogen, halogen, C _-C6 alkyl, C3-Cd alkenyl, C3-C6 alkynyl, Ci-Ce alkoxy, C-Ce alkynyloxy, C3-C6 alkynyloxy, C-C6 cycloalkyl or cycloalkoxy of C3-C6, it being possible for each of the 8 radicals mentioned above, if desired, to have 1 to 3 substituents, in each case selected from the group consisting of halogen, C6-C6 alkoxy and -CO- OR8 'R is hydrogen, C? -C6 alkyl, C? -C6 haloalkyl, C3-C6 cycloalkyl / C3-C6 alkenyl, C3-C6 alkynyl, (C? -C6 alkoxy) carbonylalkyl (from C ? -C6) or benzyl R8, R8 'independent of each other are: hydrogen, C? -C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C? -C alkyl, C3-C6 alkenyl, C3-C6 alkynyl, (C 1 -C 6) alkoxy-C 1 -C 6 alkyl, (C 1 -C 6 alkoxy) carbonylalkyl Ci-Cβ, (C 3 -C 6 alkenyloxy) carbonylalkyl Ci-Ce, phenyl or phenylalkyl of C! C6, it being possible for the phenyl group and the phenyl ring of the phenylalkyl group to be unsubstituted or to have attached thereto from 1 to 3 radicals, each selected from the group consisting of halogen, nitro, cyano, C? -C6 alkyl , haloalkyl of C? -C6, alkoxy of C_-C6 and (C? -C6 alkyl) carbonyl R9 is hydrogen or Ci-Cß alkyl R 10 is hydrogen, C?-C6 alkyl or C?-C6 alkoxy, it being possible for the last two radicals mentioned to have attached to them one of the following substituents: C?-C6 alkoxy, (C alco-alkoxy) C6) carbonyl or phenoxycarbonyl R .11 is hydrogen, C? -C6 alkyl or C? -C6 haloalkyl R, 13, R. 14 independent of each other are C? -C6 alkyl or together are a saturated 2- to 4-membered carbon chain which may be bonded thereto to an alkyl radical of C _ C6 R, 15 is hydrogen, cyano, halogen or C? -C6 alkyl R 16 is O-R23 or -N (R21) R22 R20, R23 independent of each other are hydrogen, C?-C6 alkyl / C?-C6 haloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, it being possible for each of the four groups just mentioned to be attached thereto one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C?-C6 alkoxy, Ci-Cß alkylthio, (Ci-Ce alkyl) carbonyl, (C?-C6 alkoxy) carbonyl, (alkyl) Ci-Cβ) carbonyloxy, (C3-C6 alkenyloxy) carbonyl, (C3-C6 alkynyloxy) carbonyl or Ci-Ce- alkoxy (Ci-Ce alkoxy) carbonyl; or C3-Cβ cycloalkyl, phenyl or phenylalkyl of Ci-Cß, where the phenyl rings may be unsubstituted or, in turn, may have attached to them + to one to three substituents, in each case selected from the group which consists of cyano, nitro, halogen, C? -C6 alkyl, C? -C6 haloalkyl, C? -C6 alkoxy and (C? -C6 alkoxy) carbonyl R21, R22 independently of each other are: hydrogen, Ci-Cß alkyl, C3-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-Ce haloalkyl, C?-C6 alkyloxy -Cd, (Ci-Cß alkyl) carbonyl, (C?-C6 alkoxy) carbonyl, (C?-C6 alkoxy) carbonylalkyl of i-Ce or alkylsulfonyl of CI-CO or R21 and R22 together with the nitrogen atom are a saturated or unsaturated 4- to 7-membered heterocycle which, if desired, may contain one of the following members, in addition to the carbon ring members: -O-, -S-, -N =, -NH- or -N (C? -C6 alkyl) and the salts useful for agricultural use and enol ethers of the compounds I.

Moreover, the invention relates to: the use of the compounds I as herbicides, herbicidal compositions containing the compounds I as active substances, the processes for the preparation of the compounds I and the herbicidal compositions using the compounds I, and methods of controlling undesirable vegetation using the compounds I. DE-A 40 00 624 describes the 1-phenyltriazines specifically substituted having fungicidal action. No herbicidal action is mentioned. Thiotriazines are not mentioned. EP-A 640 600 describes substituted 4-thiotriazines having a herbicidal action and which are 4-5 fused in the phenyl substituent. The subject of EP-A 584 655 and -to a certain extent- also O99 / 05125 is the aryltriazinetriones of the type of compounds I and their use as herbicides. A multiplicity of aryltriazines and aryltriotriazines falls within the general formulas; however, individual compounds having a thioketone group in the triazine moiety are not mentioned in any publication. We have found that the aryltriotriazines of the formula I as defined above have a particularly good herbicidal action. We have also found herbicidal compositions containing the compounds I and having very good herbicidal action. In addition, processes have been found for the preparation of these compositions and methods for controlling undesirable vegetation using the compounds I. Depending on the substitution model, the compounds of the formula I may contain one or more chiral centers, in which case they are present as mixtures of enantiomers or diastereomers. In the case of compounds I containing at least one olefinic residue, E / Z isomers may also be possible. The subject of the invention is not only the pure enantiomers or diastereomers but also their mixtures. Among the salts suitable for agricultural use are especially the salts of those cations, or the acid addition salts of those acids, whose cations or anions, respectively, do not adversely affect the herbicidal action of the compounds I. Thus, especially the suitable cations are the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably of calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may have attached thereto from 1 to 4 Ci-C alkyl substituents. and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 alkyl) sulfonium and sulfoxonium ions, preferably tri (C 1 -C 4 alkyl) sulfoxonium. The anions of the useful acid addition salts are mainly chloride, bromide, fluoride, acid sulfate, sulfate, diacid phosphate, acid phosphate, phosphate, nitrate, carbonate acid, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of the alkanoic acids of C? -C4, preferably format, acetate, propionate and butyrate. The organic moieties mentioned in the definition of R1 to R3, R5 to R23 and to the phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual enantiomers of the members of individual groups. All carbon chains, ie, all alkyl, alkenyl or alkynyl portions (unsubstituted or substituted), can be straight chain or branched. The halogenated substituents preferably have 1 to 5 same or different halogen atoms attached to them. The meaning of halogen is in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.

Examples of other meanings are: - C 1 -C 4 alkyl: CH 3, C 2 H 5, n-propyl, CH (CH 3) 2, n-butyl, CH (CH 3) -C 2 H 5, 2-methylpropyl or C (CH 3) 3, in particular CH 3, C 2 H 5 or CH ( CH3) 2 - haloalkyl of C _.- C: an alkyl radical of C? -C4, as mentioned, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH2F, CHF2, CF3, CH2C1, dichloromethyl, trichloromethyl , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2 , 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, C2F5, 2-fluoropropyl, 3-fluoropropyl, 2, 2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3 -chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3, 3, 3-trifluoropropyl, 3, 3, 3-trichloropropyl, CH2-C2F5, CF2-C2F5, 1- (fluoromethyl) -2-fluoroethyl , 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular CH2F, CHF2, CF3, CH2C1, 2-fluoroethyl, -chloroethyl or 2,2,2-trifluoroethyl - C alquilo-C6 alkyl: C alquilo-C alkyl as already mentioned and, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, -hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2 , 2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or -ethyl-2-methylpropyl, in particular CH 3, C 2 H 5, n-propyl, CH (CH 3) 2, n-butyl, C (CH 3) 3, n-pentyl or n-hexyl - haloalkyl of C? -C6: C? -C alkyl & as already mentioned, it is partially or completely substituted by fluorine, bromine and / or iodine, for example one of the radicals mentioned in haloalkyl of C? ~ C4 or 5- fluoro-1-pentyl, 5-chloro-l-pentyl, 5-bromo-l-pentyl, 5-iodo-l-pentyl, 5, 5, 5-trichloro-l-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-l-hexyl, 6-bromo- l-hexyl, 6-iodo-l-hexyl, 6,6-trichloro-1-hexyl or dodecafluorohexyl, in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2- trifluoroethyl C6-C6 phenylalkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-yl , 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4 phenylbut-2-yl, 1- (phenylmethyl) et-l-yl, 1- (phenylmethyl) -1- (methyl) et-l-yl or 1- (phenylmethyl) prop-1-yl, in particular benzyl or 2-phenylethyl (C6-C6 alkyl) carbonyl: CO-CH3, CO-C2H5, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1-dimethylethylcarbonyl, n-pentylcarbonyl, 1- methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4- methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1, 1 2-trimethylpropicarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, in particular CO-CH 3, CO-C 2 H 5 or CO-CH (CH 3) 2 C6-C6 alkoxy: for example OCH3 OC2H5, OCH2-C2H5, OCH (CH3) 2, n-butoxy, OCH (CH3) -C2H5, OCH2-CH (CH3) 2, OC (CH3) 3, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpro? Oxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1- ethyl-l-methylpropoxy and l-ethyl-2-methylpropoxy, in particular OCH3, OC2H5 or OCH (CH3) 2 (C6-C6 alkoxy) carbonyl: for example CO-OCH3, CO-OC2H5, CO-CH2-C2H5, CO-OCH (CH3) 2, n-butoxycarbonyl, CO-OCH (CH4) -C2H5, CO-OCH2 -CH (CH3) 2, CO-OC (CH3) 3, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, X, 2 -dimethylpropylcarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methyl-ethoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl , 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1, 1, 2-trimethylpropoxycarbonyl, 1, 2, 2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular CO -OCH3, CO-OC2H5, CO-OCH (CH3) 2 or CO-CH2-CH (CH3) "2? 4 - (Ci-Cβ alkoxy) carbonyloxy: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy .. 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1, 1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbonyloxy, 2,3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy, 2-ethylbutoxycarbonyloxy, 1,1-2- trimethylpropoxycarbonyloxy, 1,2,2-trimethylpropoxycarbonyloxy, 1-ethyl-1-methylpropoxycarbonyloxy or 1-ethyl-2-methylpropoxycarbonyloxy, in particular methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxycarbonyloxy alkylthio of C_-C6: SCH 3, SC 2 H 5, SCH 2 -C 2 H 5, SCH (CH3) 2, n-butylthio, 1-methylpropylthio, 2-ethylpropylthio, SC (CH3) 3, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n -hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-diethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2 -ethylbutylthio, 1, 1, 2-trimethylpropithio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, in particular SCH 3 or SC 2 H 5 alkylsulfonyl of C? -C6: S02-CH3, S02-C2H5, n-propylsulfonyl, S02-CH (CH3) 2, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S02-C (CH3) 3, n-pentylsulfonyl , 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl , 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1,2-trimethylpropylene sulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, in particular S0-CH 3 C 1 -C 6 -alkyl-C 6 -C 6 -alkyl: C 1 -C 6 -alkyl which is substituted by C 1 -C 6 -alkoxy as already mentioned, i.e., for example, CH 2 0CH 3, CH 2 0 C 2 H 5, n-propoxymethyl , CH2-0CH (CH3) 2, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH2-OC (CH3) 3, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, - (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- (1, 1) -dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-propoxy) propyl, 2- (1-methylethoxy) propyl, 2- (n-butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) ropyl, 2- (1,1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- ( ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (n-butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1,1-dimethylethoxy) utilo, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl c 4- (1, 1-dimethylethoxy) utilo, in particular CH2-OCH3 or 2-methoxyethyl C 1 -C 6 alkoxy (C 1 -C 6 alkoxy) carbonyl: (C 1 -C 6 alkoxy) carbonyl which is substituted by C 1 -C 6 alkoxy as already mentioned, for example CO-OCH 3 -OCH 3, CO-OCH 2 -OC2H5, CO-OCH2-OCH2-C2H5, CO-OCH2-OCH (CH3) 2, n-butoxymethoxycarbonyl, (1-methylpropoxy) methoxycarbonyl, CO-OCH2-OCH2-CH (CH3) 2, CO-OCH2-OC ( CH 3) 3, 2- (methoxy) ethoxycarbonyl, 2- (ethoxy) ethoxycarbonyl, 2- (n-propoxy) ethoxycarbonyl, 2- (1-methylethoxy) ethoxycarbonyl, 2- (n-butoxy) ethoxycarbonyl, 2- (1- methylpropoxy) ethoxycarbonyl, - (2-methylpropoxy) ethoxycarbonyl, - (1,1-dimethylethoxy) ethoxycarbonyl, - (methoxy) ropoxycarbonyl, 2- (ethoxy) psopoxycarbonyl, - (n-propoxy) propoxycarbonyl, - (1-methylethoxy) propoxycarbonyl , - - (n-butoxy) propoxycarbonyl, - (1-methylpropoxy) propoxycarbonyl, - (2-methylpropoxy) propoxycarbonyl, - (1,1-dimethylethoxy) propoxycarbonyl, - (methoxy) propoxycarbonyl, 3- (ethoxy) propoxycarbonyl, - (n-propoxy) propoxycarbonyl, - (1-methyletoxy) propoxycarbonyl, - (n-butoxy) propoxic arbonyl, - (1-methylpropoxy) propoxycarbonyl, - (2-methylpropoxy) propoxycarbonyl, - (1,1-dimethylethoxy) propoxycarbonyl, - (methoxy) butoxycarbonyl, 2- (ethoxy) butoxycarbonyl, - (n-propoxy) butoxycarbonyl, - (1-methylethoxy) -toxycarbonyl, - (n-butoxy) butoxycarbonyl, - (1-methylpropoxy) butoxycarbonyl, - (2-methylpropoxy) butoxycarbonyl, - (1,1-dimethylethoxy) butoxycarbonyl, - (methoxy) butaxycarbonyl, 3- ( ethoxy) butoxycarbonyl, - (n-propoxy) butoxycarbonyl, 3- 1 -methylethoxy) utoxycarbonyl, 3-n-butoxy) butoxycarbonyl, 3- 1-methylpropoxy) butoxycarbonyl, 3- 2-methylpropoxy) butoxycarbonyl, 3-1, 1- dimethylethoxy) butoxycarbonyl, 4-methoxy) butoxycarbonyl, 4- (ethoxy) butoxycarbonyl, n-propoxy) butoxycarbonyl, 4- 1-methylethoxy) butoxycarbonyl, 4-n-butoxy) butoxycarbonyl, 4- 1-methylpropoxy) butoxycarbonyl, 4- 2 -methylpropoxy) butoxycarbonyl, 4- 1, 1-dimethylethoxy) butoxycarbonyl, 5-methoxy) pentoxycarbonyl, 5-ethoxy) pentoxycarbonyl, 5-n-propoxy) pentoxycarbonyl, 5- 1 -metheretoxy) pentoxycarbonyl, 5- n-butoxy) pentoxycarbonyl, 5- 1-methylpropoxy) pentoxycarbonyl, 5- 2-methylpropoxy) pentoxycarbonyl, 5-1,1-dimethylethoxy) pentoxycarbonyl, 6-methoxy) hexoxycarbonyl, 6- (ethoxy) hexoxycarbonyl, 6- n-propoxy) hexoxycarbonyl, 6- 1-methylethoxy) hexoxycarbonyl, 6- n-butoxy) hexoxycarbonyl, 6- 1-methylpropoxy) hexoxycarbonyl, 6- (2-methylpropoxy) hexoxycarbonyl or 6- (1, 1- rH.-methylethoxy) hexoxycarbonyl, in particular CO-OCH2-OCH3 or CO-OCH2-OC2H5; (C?-C6 alkoxy) carbonylCi-Cß alkyl: Ci-Cd alkyl which is substituted by (C?-C6 alkoxy) carbonyl as already mentioned, for example methoxycarbonylmethyl, ethoxycarbonylmethyl, 1- (methoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 3- (methoxycarbonyl) propyl, 4- (methoxycarbonyl) butyl, 5- (methoxycarbonyl) pentyl or 6- (methoxycarbonyl) hexyl C3-C6 alkenyl: for example prop-2-en-l-yl, n-buten-4-yl, l-methylprop-2-en-l-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, n-penten-3-yl, n-penten-4-yl, l-methylbut-2-en-1-yl, 2 -methylbut-2-en-l-yl, 3-methylbut-2-en-l-yl, l-methylbut-3-en-l-yl, 2-methylbut-3-en-l-yl, 3-methylbut -3-en-l-yl, 1, l-dimethylprop-2-en-l-yl, 1,2-dimethylprop-2-en-l-yl, l-ethylprop-2-en-l-yl, n -hex-3-en-l-yl, n-hex-4-en-l-yl, n-hex-5-en-l-yl, l-methylpent-3-en-l-yl, 2-methylpent -3-en-l-yl, 3-methylpent-3-en-l-yl, 4-methylpent-3-en-l-yl, l-methylpent-4-en-l-yl, 2-methylpent-4 -in-l-yl, 3-methylpent-4-en-l-yl, 4-methylpent-4-en-l-yl, 1, l-dimethylbut-2-en-l-yl, 1,1-dimethylbut -3-en-l-yl, 1,2-dimethylbut-2-en-l-yl, 1,2-dimethylbut-3-en-l-yl, 1,3-dimethylbut-2-en-l-yl, 1 , 3-dimethylbut-3-en-l-yl, 2, 2-dimethylbut-3-en-l-yl, 2,3-dimethylbut-2-en-l-yl, 2,3-dimethylbut-3-en -l-ilo, 3,3-dimethylbut-2-en-l-yl, l-ethylbut-2-en-l-yl, 1-ethylbut-3-en-l-yl, 2-ethylbut-2-en -l-ilo, 2-ethylbut-3-en-l-yl, 1, 1, 2-trimethylprop-2-en-l-yl, 1-ethyl-l-methylprop-2-en-l-yl or l -ethyl-2-methylprop-2-en-l-yl, in p joint prop-2-en-l-yl or n-buten-4-yl C2-C6 alkenyl: ethenyl or one of the radicals mentioned in C-Cd alkenyl, in particular ethenyl or prop-2-en-l-yl: C2-C6 alkenyloxy: prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten- 3-yloxy, 1-methylprop-l-en-l-yloxy, 2-methylprop-1-en-l-yloxy, l-methylprop-2-en-l-yloxy, 2-methylprop-2-en-l- iloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methylbut-1-en-l-yloxy, 2-methylbutyl- l-en-l-yloxy, 3-methylbut-l-en-1-yloxy, l-methylbut-2-en-l-yloxy, 2-methylbut-2-en-1-yloxy, l-methylbut-3- en-l-yloxy, 2-methylbut-3-en-l-yloxy, 3-methylbut-3-en-l-yloxy, 1, l-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop- l-en-l-yloxy, 1,2-dimethylprop-2-en-l-yloxy, l-ethylprop-l-en-2-yloxy, 1-ethylprop-2-en-l-l-loxi, n -hex-1-en-l-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-l-yloxy, n-hex-4-en-l-yloxy, n-hex -5-en-l-yloxy, 1-methylpent-l-en-l-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-l-en-l-yloxy, 4-methylpent-1 -in-l-iloxy, l-methylpent-2-en-l-yloxy, 2-methylpent-2-en-l-yloxy, 3-methylpent-2-en-l-yloxy, 4-methylpent-2-en -l-iloxy, l-methylpent-3-en-l-yloxy, 2-methylpent- 3-en-l-yloxy, 3-methylpent-3-en-l-yloxy, 2-methylpent-4-en-l-yloxy, 3-methylpent-4-en-l-yloxy, 4-methylpent-4- en-l-yloxy, 1, l-dimethylbut-2-en-l-yloxy, 1, l-dimethylbut-3-en-l-yloxy, 1,2-dimethylbut-l-en-l-yloxy, 1, 2-dimethylbut-2-en-l-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-l-en-l-yloxy, 1,3-dimethylbut-2-en- l-iloxy, 1,3-dimethylbut-3-en-l-yloxy, 2,2-dimethylbut-3-en-l-yloxy, 2,3-dimethylbut-l-en-l-yloxy, 2, 3- dimethylbut-2-en-l-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-l-en-l-yloxy, 3,3-dimethylbut-2-en-l- iloxy, 1-ethylbut-l-en-l-yloxy, 1-ethylbut-2-en-l-yloxy, l-ethylbut-3-en-l-yloxy, 2-ethylbut-1-en-l-yloxy, 2-ethylbut-2-en-l-yloxy, 2-ethylbut-3-en-l-yloxy, 2-ethylbut-2-en-l-yloxy, 2-ethylbut-3-en-l-yloxy, 1, 1, 2-trimethylprop-2-en-l-yloxy, l-ethyl-l-methylprop-2-en-l-yloxy, l-ethyl-2-methylprop-l-en-1-yloxy or l-ethyl- 2-methylprop-2-en-1-yloxy, in particular prop-2-en-l-yloxy C2-C6 alkenyloxy: ethenyloxy or one of the mentioned radicals in C3-C6 alkenyloxy, in particular ethenyloxy or prop-2-en-l-yloxy C2-C6 alkenylthio: ethenylthio, prop-1-en-l-ylthio, prop-2-en-l-ylthio, 1-methylethylthio, n-buten-1-ylthio, n-buten-2-ylthio, n- buten-3-ylthio, 1-methylprop-l-en-l-ylthio, 2-methylprop-l-en-l-ylthio, l-methylprop-2-en-l-ylthio, 2-methylprop-2-en- l-ilthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1-methylbut-1-en-l-ylthio, 2- methylbut-l-en-l-ylthio, 3-methylbut-1-en-l-ylthio, l-methylbut-2-en-l-ylthio, 2-methylbut-2-en-l-ylthio, 3-methylbutyl- 2-en-l-iltio, 1-methylbut-3-en-l-iltio, 2-methylbut-3-en-l-itio, 3-methylbut-3-en-1-iltio, 1, l-dimetilprop- 2-en-l-ylthio, 1,2-dimethylprop-l-en-l-ylthio, 1,2-dimethylprop-2-en-l-ylthio, l-ethylprop-l-en-2-ylthio, l- ethylprop-2-en-l-ilthio, n-hex-1-en-l-ilthio, n-hex-2-en-l-ilthio, n-hex-3-en-l-ilthio, n-hex- 4-en-l-iltio, n-hex-5-en-l-iltio, 1-methylpent-l-en-l-iltio, 2-methylpent-l-en-l-iltio, 3-methylpent-1- en-l-iltio, 4-methylpent-l-en-l-iltio, 1-methylpent-2-en-l-iltio, 2-methylpent-2-en-l-iltio, 3-methylpent-2-en- l-ilthio, 4-methylpent-2-en-l-ilthio, 1-methylpe nt-3-en-l-iltio, 2-methylpent-3-en-l-iltio, 3-methylpent-3-en-l-iltio, 4-methylpent ~ 3-en-l-iltio, 1-methylpent- 4-en-l-iltio, 2-methylpent-4-en-l-iltio, 3-methylpent-4-en-l-iltio, 4-methylpent-4-en-l-iltio, 1,1-dimethylbut- 2-en-l-ylthio, 1, l-dimethylbut-3-en-l-ylthio, 1,2-dimethylbut-l-en-l-ylthio, 1,2-dimethylbut-2-en-l-ylthio, 1, 2-dimethylbut-3-en-l-ylthio, 1,3-dimethylbut-l-en-1-ylthio, 1,3-dimethylbut-2-en-l-ylthio, 1,3-dimethylbut-3- en-l-ilthio, 2, 2-dimethylbut-3-en-l-ylthio, 2,3-dimethylbut-l-en-l-ylthio, 2,3-dimethylbut-2-en-l-ylthio, 2, 3-dimethylbut-3-en-l-ylthio, 3, 3-dimethylbut-l-en-1-ylthio, 3, 3-dimethylbut-2-en-l-ylthio, 1-ethylbut-l-en-1- iltio, l-etilbut-2-en-l-iltio, l-etilbut-3-en-l-iltio, 2-etilbut-l-en-l-iltio, 2-etilbut-2-en-l-iltio, 2-ethylbut-3-en-l-ylthio, 1,1, 2-trimethylprop-2-en-l-ylthio, l-ethyl-l-methylprop-2-en-l-ylthio, l-ethyl-2- methylprop-1-en-l-ylthio or l-ethyl-2-methylprop-2-en-l-ylthio, in particular ethenylthio or prop-2-en-l-ylthio C3-C6 alkynyl: prop-1-yn-l-yl, prop-2-yn-l-yl, n-but-1-yn-l-yl, n-but-l-yn-3-yl, n-but-l-in-4-yl, n-but-2-yn-l-yl, n-pent-1-yn-l-yl, n-pent-l-in-3-yl, n- pent-1-in-l-yl, n-pent-l-in-5-yl, n-pent-2-yn-l-yl, n-pent-2-yn-4-yl, n-pent 2-in-5-yl, 3-methylbut-l-in-3-yl, 3-methylbut-l-in-4-yl, n-hex-1-yn-l-yl, n-hex-l- in-3-yl, n-hex-l-in-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-y-yl, n-hex-2-yl l -yl, n-hex-2-in-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-in-l- ilo, n-hex-3-in-2-yl, 3-methylpent-l-yn-l-yl, 3-methylpent-l-in-3-yl, 3-methylpent-l-in-4-yl, 3- methylpent-l-in-5-yl, 4-methylpent-l-yn-l-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particular prop-2-in-l-ilo - C2-C6 alkynyl: ethynyl or one of the radicals mentioned in C3-C6 alkynyl, in particular ethynyl or prop-2-yn-l-yl: - C3-C6 alkynyloxy: prop-1-yn-l-yloxy, prop-2-yn-l-yloxy, n-but-1-yn-l-yloxy, n-but-l-in-3-yloxy , n-but-l-in-4-yloxy, n-but-2-yn-l-yloxy, n-pent-1-yn-l-yloxy, n-pent-l-in-3-yloxy, n -pent-l-in-4-yloxy, n-pent-1-in-5-yloxy, n-pent-2-yn-l-yloxy, n-pent-2-yn-4-yloxy, n-pent -2-in-5-yloxy, 3-methylbut-l-in-3-yloxy, 3-methylbut-l-in-4-yloxy, n-hex-1-yn-l-yloxy, n-he? - 1-in-3-yloxy, n-hex-l-in-4-yloxy, n-hex-l-in-5-yloxy, n-hex-l-in-6-yloxy, n-hex-2- in-l-iloxy, n-hex-2-in-4-yloxy, n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-in l-iloxy, n-hex-3-in-2-yloxy, 3-methylpent-l-in-l-yloxy, 3-methylpent-l-in-3-yloxy, 3-methylpent-l-in-4- iloxy, 3-methylpent-l-in-5-yloxy, 4-methylpent-l-in-l-yloxy, 4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy in particular prop-2-in-l-yloxy; - C2-C6 alkynyloxy: ethynyloxy or one of the radicals mentioned in C3-C6 alkynyloxy, in particular ethynyloxy or prop-2-yn-l-yloxy: - C2-C6 alkynylthio: ethynylthio or one of the radicals mentioned in C3-C6 alkynylthio, in particular ethynylthio or prop-2-yn-l-ylthio; - (C3-Ce alkyloxy) carbonyl: prop-1-en-1-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, 1-methylethynyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2-yloxycarbonyl, n-buten-3-yloxycarbonyl, 1-methylprop-1-en-l-yloxycarbonyl, 2-methylprop-1-en-l-yloxycarbonyl, l-methylprop-2-en-l-yloxycarbonyl, 2-methylprop-2- en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1-methylbut-1-en-l-yloxycarbonyl, 2-methylbut-1-en-1-yloxycarbonyl, 3-methylbut-1-en-1-yloxycarbonyl, 1-methylbut-2-en-1-yloxycarbonyl, 2-methylbut-2-en-1-yloxycarbonyl, 3- methylbut-2-en-l-yloxycarbonyl, 1-methylbut-3-en-l-yloxycarbonyl, 2-methylbut-3-en-1-yloxycarbonyl, 3-methylbut-3-en-l-yloxycarbonyl, 1,1- dimethylprop-2-en-l-yloxycarbonyl, 1,2-dimethylprop-l-en-1-yloxycarbonyl, 1,2-dimethylprop-2-en-l-yloxycarbonyl, l-ethylprop-l-en-2-yloxycarbonyl, 1-ethylprop-2-en-l-yloxycarbonyl, n-hex-l-en-1-yloxycarbonyl, n-hex-2-en-l-yl arbonium, n-hex-3-en-1-yloxycarbonyl, n-hex-4-en-l-yloxycarbonyl, n-hex-5-en-l-yloxycarbonyl, 1-methylpent-l-en-l-yloxycarbonyl, 2-methylpent-l-en-l-yloxycarbonyl, 3-methylpent-1-en-l-yloxycarbonyl, 4-methylpent-l-en-l-yloxycarbonyl, l-methylpent-2-en-l-yloxycarbonyl, 2- methylpent-2-en-1-yloxycarbonyl, 3-methylpent-2-en-l-yloxycarbonyl, 4-methylpent-2-en-l-yloxycarbonyl, 1-methylpent-3-en-l-yloxycarbonyl, 2-methylpentyl- 3-en-l-yloxycarbonyl, 3-methylpent-3-en-l-yloxycarbonyl, 4-methylpent-3-en-l-yloxycarbonyl, l-methylpent-4-en-l-yloxycarbonyl, 2-methylpent-4- en-l-yloxycarbonyl, 3-methylpent-4-en-l-yloxycarbonyl, 4-methylpent-4-en-l-yloxycarbonyl, 1, l-dimethylbut-2-en-l-yloxycarbonyl, 1, l-dimethylbutyl- 3-en-l-yloxycarbonyl, 1,2-dimethylbut-1-en-l-yloxycarbonyl, 1,2-dimethylbut-2-en-l-yloxycarbonyl, 1,2-dimethylbut-3-en-l-yloxycarbonyl, 1, 3-dimethylbut-l-en-l-yloxycarbonyl, 1,3-dimethylbut-2-en-l-yloxycarbonyl, 1,3-dimethylbut-3-en-l-yloxycarbonyl, 2,2-dimethylbut-3- en-l-iloxicar bonyl, 2- 3-dimethylbut-l-en-l-yloxycarbonyl, 2,3-dimethylbut-2-en-l-yloxycarbonyl, 2,3-dimethylbut-3-en-l-yloxycarbonyl, 3, 3-dimethylbut-l-en-l-yloxycarbonyl, 3, 3-dimethylbut-2-en-l-yloxycarbonyl, 1-ethylbut-l-en-1-yloxycarbonyl, l-ethylbut-2-en-l -alkoxycarbonyl, 1-ethylbut-3-en-1-yloxycarbonyl, 2-ethylbut-l-en-l-yloxycarbonyl, 2-ethylbut-2-en-l-yloxycarbonyl, 2-ethylbut-3-en-l-yloxycarbonyl , 1,1, 2-trimethylprop-2-en-1-yloxycarbonyl, l-ethyl-l-methylprop-2-en-l-yloxycarbonyl, l-ethyl-2-methylprop-l-en-l-yloxycarbonyl or -ethyl-2-methylprop-2-en-l-yloxycarbonyl, in particular prop-2-en-l-yloxycarbonyl (C3-Ce alkynyloxy) carbonyl-C6-C6alkyl: Ci-C3alkyl which is substituted by (C3-Ce) alkyloxycarbonyl as already mentioned, preferably prop- 2-en-l-yloxycarbonyl, for example, prop-2-en-l-yl-oxycarbonylmethyl; (C3-C6 alkynyloxy) carbonyl: prop-1-yn-1-yloxycarbonyl, prop-2-yn-l-yloxycarbonyl, n-but-1-yn-1-yloxycarbonyl, n-but-l-yn-3 -alkoxycarbonyl, n-but-l-in-4-yloxycarbonyl, n-but-2-yn-l-yloxycarbonyl, n-pent-1-yn-l-yloxycarbonyl, n-pent-l-yn-3-yloxycarbonyl , n-pent-l-inyloxycarbonyl, n-pent-1-yn-5-yloxycarbonyl, n-pent-2-yn-l-yloxycarbonyl, n-pent-2-yn-4-yloxycarbonyl, n- pent-2-in-5-yloxycarbonyl, 3-methylbut-l-in-3-yloxycarbonyl, 3-methylbut-l-in-4-yloxycarbonyl, n-hex-1-yn-l-yloxycarbonyl, n-hex- l-in-3-yloxycarbonyl, n-hex-l-in-4-yloxycarbonyl, n-hex-1-yn-5-yloxycarbonyl, n-hex-l-in-6-yloxycarbonyl, n-hex-2- in-l-yloxycarbonyl, n-hex-2-yn-4-yloxycarbonyl, n-hex-2-yn-5-yloxycarbonyl, n-hex-2-yn-6-yloxycarbonyl, n-hex-3-yne l-ioxycarbonyl, n-hex-3-yn-2-yloxycarbonyl, 3-methylpent-l-yn-l-yloxycarbonyl, 3-methylpent-l-yn-3-yloxycarbonyl, 3-methylpent-l-yn-4- Iloxycarbonyl, 3-methylpent-l-in-5-yloxycarbonyl, 4-methylpent-l-yn-l-yloxycarbonyl, 4-methylpent-2-yn-4-yl xicarbonyl or 4-methylpent-2-yn-5-yloxycarbonyl, in particular ethynyloxycarbonyl or prop-2-yn-l-yloxycarbonyl C3-C6 cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl C3-C6 cycloalkyl: for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1- (cyclopropyl) ethyl, 1- (cyclobutyl) ethyl, 1- (cyclopentyl) ethyl, 1- (cyclohexyl) ethyl, 2- (cyclopropyl) ethyl , 2- (cyclobutyl) ethyl, 2- (cyclopentyl) ethyl, 2- (cyclohexyl) -ethyl, 3- (cyclopropyl) propyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl) propyl , 4- (cyclopropyl) butyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl) butyl or 4- (cyclohexyl) butyl, in particular cyclopentylmethyl or cyclohexylmethyl - C3-C6 cycloalkoxy: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy - C3-C6 cycloalkylthio: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, The aza heterocycles of 4 to 7 members which, in addition to the members of the carbon ring, may also contain, as a member of the ring, an oxygen or sulfur atom, are, for example, azetidin-1-yl, pyrrolidin-1. -yl, isoxazolidin-2-yl, isothiazolidin-2-yl, oxazolidin-3-yl, thiazolidin-3-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl and azepin-1-yl . For the purpose of the use of the l-aryl-4-thiatriazines of the formula I according to the invention as herbicides, the variables preferentially have the following meanings, in each case alone or in combination: R1 is hydrogen, amino or methyl, in particular methyl R2 is hydrogen, amino or methyl, in particular methyl R3 is hydrogen or fluorine, in particular fluorine R4 is cyano or halogen, in particular: a) cyano b) chloro And it's the methino group or, along with R, it's a bridge > C- 0-C (R6) = N-, in particular: a) the methino group b) together with R5 a bridge > C-0-C (R6) = N- R3 is: 1) on the one hand, hydrogen, nitro or halogen on the other hand, C?-C6 alkyl or C?-C6 haloalkyl on the one hand, C alco-C alco alkoxy on the other hand; Cß or Ci-Ce alkylthio, it being possible for each of these two radicals, if desired, to have attached to it one of the following substituents: cyano, -CO-R8, -CO-OR8 or -CO-N (R8 ) -R9, in particular methoxy, ethoxy, n-propyloxy, isopropoxy, methylthio, ethylthio, n-propylthio or isopropylthio, it being possible for each of these 8 radicals, if desired, to be attached to the The same substituent is -CO-OR8, especially preferably (C3-C6 alkenyloxy) carbonylmethoxy, (C3-Cg alkynyloxy) carbonylmethoxy, 1- [(C3-C6 alkenyloxy) carbonyl] et-1-yloxy, - [(alkynyloxy of C3-Ce) carbonyl] et-1-yloxy, C 1 -C 4 alkoxy (C 1 -C 4 alkoxy) carbonylmethoxy, 1- [C 1 -C 4 alkoxy (C 4 -C 4 alkoxy) carbonyl] et-1 -iloxy, (C3-Ce alkenyloxy) carbonylmethylthio, (C3-C6 alkynyloxy) carbonylmethylthio, 1- [(C3-C6 alkenyloxy) carbonyl] et-1-ylthio, 1- [(C3-C6 alkynyloxy) carbonyl] et-1-ylthio, C-alkoxy] ? -C- (C? -C4 alkoxy) carbonylmethylthio or 1- [CC- (C? -C) alkoxy] carbonyl] et-1-ylthio alkoxy on the other hand, C3-C6 cycloalkoxy, C3 cycloalkylthio -C6, C2-C6 alkenyloxy, C2-C6 alkenylthio, C-C6 alkynyloxy or C2-C6 alkynylthio, it being possible for each of these 6 radicals, if desired, to have attached one of the following substituents: cyano , -CO-R8, -CO-OR8 or -CO-N (R8) -R9, in particular cyclopentyloxy, cyclopentylthio, allyloxy, allythio, propargylloxy or propargylthio on the other hand, -CO-R 11 -C (R) = C (R15) -CO-R16, -CH (R 11) -CH (R 15) -CO-R 16, -C (R 10 = N-OR ', -N (R 21, -R 22 or -CO-N (R 21) -R 22, in particular CHO , -CII = C (R15) -CO-R16, -CH2-CH (R15) -CO-R16, -CH = N-0R7, -C (CH3) = N-OR7, -N (R21) -R22 or -CO-N (R21) -R22 on the other hand, -CO-OR '20 R is hydrogen, C3-C6 cycloalkyl, C3-Ce alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl-C4-C4alkyl or C4-C4alkyloxy-C4alkyl, in particular C3-C6 alkenyl R is hydrogen, Ci-Cß alkyl, C3-C6 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl-C alquiloC alkyl or C?-C4 alkyloxy C? -C4, in particular C? -C6 alkyl R is hydrogen R .11 is hydrogen R15 is hydrogen, halogen or C6-C6 alkyl, in particular hydrogen, chlorine, bromine or methyl, especially preferably chlorine R 20 is C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, alkoxy C? -C4-C? -C4 alkyl, (alkenyloxy C3-C6) carbonylmethyl, (3-C6 alkynyloxy) carbonylmethyl, 1- (alkenyloxy C3-Ce) carbonyl-et-1-yl, 1- (alkynyloxy) C3-Ce) carbonyl-et-1-yl, C 1 -C 4 alkoxy (alkoxy C? -C4) carbonylmethyl, 1- [C? -C4 alkoxy (alkoxy C1-C4) carbonyl] -et-l-yl, 2- [(C3-C6 alkenyloxy) carbonyl] -prop-2-yl, C3-C6 cycloalkyl or C3-C3-Ce-alkyl of C? -C4 R '23 is hydrogen, C?-C6 alkyl, C3-Ce alkenyl or C3-C6 alkynyl, it being possible for the three groups just mentioned to have attached to these in each case one of the following radicals: C-alkoxy. -C6, (C? -C6 alkoxy) carbonyl or (C3-C6 alkenyloxy) carbonyl.

Very particular preference is given to the l-aryl-4-thiotriphialazinines of the formula (= I, where R 2 = methyl and Y the methino group) in particular the compounds Ia.l to the 720 which are listed in the following Table 1: Table 1 Other particularly preferred l-aryl-4-t-otriazines are those of the formula Ib, in particular the compounds Ib.la Ib.720, which differ from the corresponding compounds Ia.la la. 720 only by the fact that R2 is amino: Other particularly preferred l-aryl-4-thiotriazines are those of the formula le. { = I, where Y + R3 > C-0-C (R6) = N-} in particular the compounds Ic.l to Ic.55, which are listed in Table 2 below: Table 2 The l-aryl-4-thiatriazines of the formula I can be obtained by different routes, in particular by one of the following processes: A) In the same way as in J. Chem. Soc. Perkin Trans. (1982), 1321 With regard to the conditions for carrying out the reaction, see the aforementioned reference.

B) In the same way as in J. Chem. Soc. Perkin Trans. (1992), 1139 With respect to the reaction conditions, see the aforementioned reference.

According to a preferred process, which constitutes a further subject of the invention, the 1-aryl-4-thiotriazines according to the invention are prepared by reacting aryl isocyanates with thioureas, followed by cyclization.

According to an especially preferred embodiment of the process C according to the invention, the isocyanate reacts with the thiourea in the presence of an activated carbon dioxide source. Preferred examples which may be mentioned in this case are carbodiimidazole, phosgene, diphosgene and triphosgene, and chloroform esters. The process (C)) according to the invention and the processes (A)) and (B)) for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a convenient reaction aid.

Convenient reaction aids are usually customary organic or inorganic acid or base acceptors. These preferably include the acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides of alkali metals or alkaline earth metals, for example sodium acetate, potassium acetate, calcium acetate, lithium amide, sodium amide, amide potassium, calcium amide, sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, potassium bicarbonate, calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride, calcium hydride, lithium hydroxide, sodium hydroxide, hydroxide of potassium, calcium hydroxide, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide, non-sodium isopropoxide, non-potassium isopropoxide, sodium n-, iso-, sec- or ter-butoxide or n- , iso-, sec- or potassium tert-butoxide. Other basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-di ethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2, -dimethyl-, 2,6-dimethyl-, 3, -dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine , 1/4-diazabicyclo [2,2,2] octane (DABCO), 1/5-diazabicyclo [4, 3, 0] non-5-ene (DBN) or 1/8-diazabicyclo [5, 4, 0 ] undec-7-ene (DBU). Process (C)) according to the invention and processes (A)) and (B)) for the preparation of the compound of formula (I) are preferably carried out in the presence of a diluent, suitable diluents are, in Generally, the usual organic solvents. These preferably include aliphatic, alicyclic and aromatic non-halogenated or halogenated hydrocarbons, eg, pentane, hexane, heptane, petroleum ether, ligroin, benzene, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, ethylcyclohexane, dichloromethane (chloride). of methylene), trichloromethane (chloroform) or tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tertiary butyl ether (MTBE), ethyl tertiary butyl ether, methyl tertiary pentyl ether (TAME), ethyl tertiary pentylether, tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether and diethylene glycol diethyl ether; dialkyl ketones such as acetone, butanone (methyl ethyl ketone), methyl isopropyl ketone and methyl isobutyl ketone; nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile; amides such as N, N-dimethylformamide (DMF), N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone and hexamethylphosphoric triamide; esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate-and sec-butyl acetate; sulfoxides such as d-methylsulfoxide; alkanols such as methanol, ethanol, n-propanol, isbpropanol, n-, iso-, sec- and tert-butanol; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; mixtures of these with water, or pure water. When processes (B)) and (C)) are performed, the reaction temperatures may vary within a substantial range. In general, the process is carried out at temperatures from 0 to 200 ° C, preferably at 10 to 150 ° C, in particular at 20 ° C up to the boiling point of the reaction mixture in question. To perform processes (A)), (B)) and (C)), raw materials are generally used in approximately equimolar quantities. However, it is also possible to use in each case one of the components in a larger excess, approximately up to twice the molar amount of the other component. The processes (A)), (B)) and (C)) are conveniently carried out at atmospheric pressure or at the inherent pressure of the reaction mixture in question. However, the processes can also be carried out at elevated or reduced pressure, generally at 0.1 to 10 bar. The reaction mixtures in question are generally treated by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction or by removing the solvent, performing the partition of the residue. in a mixture of water and a suitable organic solvent and treating the organic phase to reach the product. In general, l-aryl-4-thiotriazines I can be prepared by one of the aforementioned synthetic processes. However, for economic or process engineering reasons, it may be more convenient to synthesize some compounds I from similar l-aryl-4-thiotriazines which, however, differ in particular with respect to the meanings of the radicals R5, in a form known per se, for example by hydrolysis, esterification, transesterification, amidation, acetalization, hydrolysis of the acetal, condensation reaction, ittig reaction, Peterson olefination, etherification, alkylation, oxidation or reduction. The preparation of l-a ^ il-4-thiotriazines I can be carried out to obtain them as isomeric mixtures; if desired, however, these can be solved by methods customary for this purpose, such as crystallization or chromatography, also on an optically active absorbate to obtain the pure isomers. The pure optically active isomers can be synthesized conveniently from the corresponding optically active starting materials. The salts useful for agricultural use of the compounds I can be formed by reaction with a base of the cation in question, preferably an alkali metal hydroxide or alkali metal hydride, or by reaction with an acid of the anion in question, preferably the hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid? nitric acid. The salts of I whose metal ion is not an alkali metal ion can also be prepared in the customary manner by double decomposition of the alkali metal salt in question, and the salts of ammonium, phosphonium, sulfonium and sulfoxonium by means of ammonia, hydroxide of phosphonium, sulfonium hydroxide or sulfoxonium hydroxide. The compounds I and their salts useful for agricultural use - as mixtures of isomers and also in the form of pure isomers - are suitable for use as herbicides. The herbicidal compositions comprising I effect very good vegetation control over uncultivated areas in particular at high application rates. These make very efficient control of broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without harming the cultivated plants to a significant degree. This effect is particularly evident at low application rates. Depending on the method of application in question, the compounds I, or the herbicidal compositions containing them, can also be used in another number of crop plants to eliminate undesirable plants. The following are examples of suitable crops: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napohrassica. Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius. Carya illinoineneis, Citrus lemon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota. Elaeis guineensis. Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis. Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia. Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Ozyra sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus pérsica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. In addition, compounds I can also be used in crops that have become tolerant to the action of herbicides through breeding, including genetic manipulation methods. The compounds I, or the herbicidal compositions containing them, can be used, for example, in the form of aqueous solutions ready for spraying, powders, suspensions, suspensions or dispersions with a high percentage of aqueous, oily or other, emulsions, oil dispersions, pastes, powders, materials for dispersion or granules, by means of aspersion, atomization, dusting, dispersion or irrigation. The forms of use depend on the proposed objectives; in any case, these should guarantee the finest possible distribution of the active ingredients according to the invention. Suitable inert auxiliaries are mainly: fractions of mineral oils from medium to high boiling point, such as kerosene and diesel oil, in addition to coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example amines, such as N-methylpyrrolidone, and water. The aqueous forms of use can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or granules dispersible in water by adding water. To prepare emulsions, pastes or oily dispersions, the l-aryl-4-thiotriazines I, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, thickener, dispersant or emulsifier. Otherwise, it is 6d it is possible to prepare concentrates containing the active ingredient, the wetting agent, thickener, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water. Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkyl aryl sulfonates, alkyl, lauryl ether and sulfates of fatty alcohols, and salts of sulphonated hexa-, hepta- and octadecanols, and also of glycol ethers of fatty alcohols, condensates of sulfonated naphthalene and their derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octyl phenol ether, isooctyl-, octyl- or nonylphenol ethoxylated, alkylphenyl polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol / ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, liqueurs re lignosulfite or methylcellulose siduals. The powders, dispersion materials and powders can be prepared by mixing or grinding the active ingredients together with a solid carrier. The granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to the solid carriers. The solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, clay, clay earth, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium, crushed synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and products of plant origin such as cereal flour, tree bark flour, wood flour and nut shell flour, cellulose powder or other solid carriers. The concentrations of the active ingredients I in ready-to-use products can vary within wide ranges. In general, the formulations contain from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% up to 100%, preferably 95% up to 100% (according to the NMR spectrum).

The following formulation examples illustrate the preparation of these products: parts by weight of compound No. 3 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of 8 to 10 moles of ethylene oxide to 1 mole of N-monoethanolamide of the acid oleic, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. The solution is poured into 100,000 parts by weight of water by finely distributing to obtain an aqueous dispersion containing 0.02% by weight of the active ingredient.

II. 20 parts by weight of compound No. 5 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 moles of ethylene oxide for 1 mole of iooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. The solution is poured into 100,000 parts by weight of water and the fine distribution therein provides an aqueous dispersion containing 0.02% by weight of the active ingredient.

III. 20 parts by weight of the active ingredient No. 12 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from boiling point 210 to 280 ° C and 10 parts by weight of the product of addition of 40 moles of ethylene oxide to one mole of castor oil. By emptying the solution into 100,000 parts by weight of water and distributing it finely therein, an aqueous dispersion containing 0.02% by weight of the active ingredient is obtained.

IV. 20 parts by weight of the active ingredient No. 32 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid of a residual sulphite liquor and 60 parts by weight of weight of powdery silica gel, and the mixture is ground in a hammer mill. The fine distribution of the mixture in 20,000 parts by weight of water produces a spray mixture containing 0.1% by weight of the active ingredient.

V. 3 parts by weight of the active ingredient No. 36 are mixed with 97 parts by weight of finely divided kaolin. This produces a powder containing 3% by weight of the active ingredient.

SAW. 20 parts by weight of the active ingredient No. 41 are intimately mixed with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of polyglycol ether fatty alcohol, 2 parts by weight of the sodium salt of a phenol / urea condensate / formaldehyde and 68 parts by weight of a paraffin mineral oil. This produces a stable oil dispersion.

VII. 1 part by weight of compound No. 42 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This produces a stable emulsion concentrate.

VIII. 1 part by weight of compound No. 64 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (= non-ionic emulsifier based on ethoxylated castor oil, BASF AG). This produces a stable emulsion concentrate.

The active ingredients I or the herbicidal compositions can be applied before or after the onset. If the active ingredients are less well tolerated by certain crop plants, it is possible to use application techniques in which the herbicidal compositions are sprayed, with the help of the spraying equipment, in such a way that they come into contact as little as possible, if they come in contact, with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of the undesirable plants that grow below, or the surface of the bare soil (post-directed, by channel) . The application rates of the active ingredient I are from 0.001 to 3.0, preferably 0.01 to 1.0 kg of the active ingredient (ai) per ha, depending on the control objective, the season, the plants chosen and the growth stage. To broaden the spectrum of action and achieve synergistic effects, l-aryl-4-thiotriazines I can be mixed with a large number of representatives of other groups of herbicides or growth regulating active ingredients and then applied concomitantly. Suitable components for mixtures are, for example, 1,2-thiadiazoles, 1,3-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, aryloxy- / hetaryloxyalkane acids and their derivatives, benzoic acid and its derivatives. , benzothiadiazinones, 2- (hetaroyl / aroyl) -1, 3-cyclohexandiones, hetaryl aryl ketones, benzisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives , diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyl uracils, imidazoles, imidazolinones, N-phenyl-3, 4 , 5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazin ace, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonyl ureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils. Furthermore, it may be convenient to apply the compounds I, alone or in combination with other herbicides, together as a mixture with other agents for crop protection, for example with pesticides or agents for controlling fungi or phytopathogenic bacteria. Likewise, miscibility is important with solutions of mineral salts that are used to treat nutrient deficiencies and elements in traces. Non-phytotoxic oils and oily concentrates can also be added.

Preparation examples Example 1 (Compound No. 38) 3- (2,4-difluorophenyl) -1,5-dimethyl-6-thioxo- [1,3,5] triazine-2,4-dione 31 g of 2,4-difluorophenyl isocyanate and 64.9 g of carbodiimidazole were added in succession to 20.8 g of N, N'-dimethylthiourea in 500 ml of toluene and 1 ml of triethylamine. This mixture was stirred first for 3 hours at 60-65 ° C and then for 12 hours at 80-85 ° C. After cooling to room temperature, the mixture was washed three times with 100 ml portions of water, and the organic phase was dried over sodium sulfate. After the distillation of the low-boiling fractions, 48 g of the desired product of melting point 156-159 ° C remained.

Example 2 (Compound No. 40) 2-chloro-5- (3, 5-dimethyl-2,6-dioxo-4-thioxo- [1, 3, 5] triazinan-1-yl) -benzaldehyde O-ethyl oxime 2. 8 g of 3-ethoxyiminoethyl-4-chlorophenyl isocyanate and 4 g of carbodiimidazole were added in succession to 1.3 g of N, N'-dimethylurea in 20 ml of toluene and 0.4 ml of triethylamine. This mixture was stirred first for 2 hours at 60 ° C and then for 4 hours at 80 ° C. After cooling to room temperature, the mixture was washed four times with 20 ml portions of water, and the organic phase was dried over sodium sulfate. The residue that remained after the solvent had been distilled was purified by chromatography on silica gel (mobile phase: cyclohexane / ethyl acetate). Yield: 2.02 g; p.f .: 139-141 ° C.

Example 3 (Compound No. 1) 3- (4-Chloro-2-fluoro-5-hydroxyphenyl) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazine-2,4-dione 3 ml of triethylamine and then a solution of 22.4 g (91.2 mmol) of 4-chloro-2-fluoro-5- (methoxycarbonyloxy) phenyl isocyanate in 100 ml of toluene were added dropwise at about 20 ° C to a solution 9.5 g (91.2 mmol) of N, N '-dimethylthiourea in ml of toluene. After the addition of 29.6 g (182.5 mmol) of carbodiimidazole, the mixture was heated for 3 hours at 80 ° C. The reaction mixture was stirred overnight at about 20 ° C, then washed three times with water and finally reduced pressure was concentrated. The crude product was purified by column chromatography (mobile phase: cyclohexane / ethyl acetate = : 1). Yield: 18.1 g (63%); p.f .: 242-246 ° C.

Example 4 (Compound No. 11) 2- [2-chloro-5- (3, 5-dimethyl-2,6-dioxo- [1, 3, 5] triazinan-1-yl) -4-fluorophenoxy] ropionate alila. (racamate) -CO-OCH2-CH * CH2 0. 37 g (2.65 mmol) of K2Co3 and 0.51 g (2.65 mmol) of allyl 2-bromopropionate rae. were added at approximately 20 ° C to a solution of 0.80 g (2.52 inmol) of 3- (4-chloro-2-fluoro-5-hydroxyphenyl) -1,5-dimethyl-6-thioxo- [1, 3, 5 ] triazine-2, -dione in 15 ml of dimethylformamide. After the reaction mixture had been stirred for 2 hours at approximately 20 ° C, it was stirred in ice water. The product was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over magnesium sulfate and then concentrated. The crude product (1.18 g) was purified by column chromatography (mobile phase: cyclohexane / ethyl acetate = 15: 1). Yield: 0.88 g (81%); 2H NMR (270 MHz, in CDC13): d [ppm] = 1.7 (d, 3H), 3.8 (s, 6H), 4.6 (m, 2H), 4.7 (q, 1H), 5.2 (d, 1H), 5.9 (m, 1H), 6.9 (d, 1H), 7.3 (d, 1H).

Example 5 (Compound No.12) (R) -2- [2-chloro-5- (3,5-dimethyl-2,6-dioxo- [1,3,5] triazine-1-yl) -4- alipyl fluorophenoxy] propionate (R isomer) 0. 38 g (1.89 mmol) of diisopropyl azodicarboxylate was added dropwise at 0 ° C over the course of 5 minutes to a solution of 0.50 g (1.58 mmol) of 3- (4-chloro-2-fluoro-5-hydroxyphenyl) ) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazinan-2,4-dione, 0.20 g (1.58 mmol) of allyl S-lactate and 0.48 g (1.81 mmol) of triphenylphosphine. Then, the mixture was stirred for 2 hours at 0-5 ° C, after which the reaction mixture was concentrated under reduced pressure. The crude product was taken up in methylene chloride. The resulting solution was washed twice with water, then dried over magnesium sulfate and finally concentrated. The crude product (1.88 g) was purified by column chromatography (mobile phase: cyclohexane / ethyl acetate = 9: 1). Yield: 0.64 g (94%); XH NMR see Example 4.

Example 6 (Compound No. 24) (R) -2- [2-chloro-5- (3, 5-dimethyl-2,6-dioxo-4-thioxo- [1, 3, 5] triazinan-1- il) -4-fluorophenoxy] cyclobutylmethyl propionate (R-isomer) 36 mg (0.125 mmol, 10 mol%) of Ti [OCH (CH 3) 2] 4 were added to a solution of 504 mg (1.25 mmol) of (R) -2- [2-chloro-5- (3, 5 methyl-dimethyl-2,6-dioxo- [1,3,5] triazin-1-yl) -4-fluorophenoxy] -propionate in 10 ml of cyclobutylmethanol. The resulting mixture was heated for 5 hours at reflux temperature, after which the reaction mixture was poured into ice water. The product of value that was formed was extracted with ethyl acetate (four times). The combined organic phases were subsequently dried over magnesium sulfate and then concentrated. The resulting crude product was purified by column chromatography (mobile phase: cyclohexane / ethyl acetate = 25: 1). Yield: 410 mg (72%).

XH NMR (400 MHz, in CDC13): d [ppm] = 1.7 (d, 3H), 1.7 (m, 2H), 1.85 (m, 2H), 2.0 (m, 2H), 2.6 (quint., 1H), 3.8 (2s, je 3H), 4.1 (m, 2H), 4.7 (q, 1H), 6.9 (d, 1H), 7.35 (d, 1H).

Example 7 (Compound No. 17) 2-Chloro-5- (3,5-dimethyl-2,6-dioxo-4-thioxo- [1, 3, 5] triazinan-1-yl) -4-fluorobenzoic acid Method A: 4.98 g (12.9 mmol) of 2-chloro-5- (3,5-dimethyl-2,6-dioxo-4-thioxo [1, 3, 5] triazinan-1-yl) -4-fluorobenzoate Isopropyl and 25 ml of concentrated sulfuric acid were heated for 7 hours at 80 ° C. then, the reaction mixture was carefully viewed in ice water. The solid fraction that had formed was separated and washed with water until neutral. After drying, 2.62 g (59%) of the desired acid was obtained; p.f. 225-229 ° C.

Method B: 108 mg (0.30 mmol) of 2-chloro-5- (3,5-dimethyl-2,6-dioxo-4-thioxo- [1, 3, 5] triazinan-1-yl) -4-fluorobenzoate of methyl and 150 mg 80.75 mmol) of trimethylsilane iodine were heated for 2 hours at 100 ° C. After cooling, methyl terbutyl ether and a saturated aqueous solution of sodium bicarbonate were added to the reaction mixture (at pH 8). The aqueous phase was subsequently separated and acidified with hydrochloric acid at 10. concentration (pH 5). It was then extracted three times with methylene chloride. The combined methylene chloride phases were then dried over magnesium sulfate and finally concentrated. Yield: 70 mg (67%); p.f. 225-229 ° C.

In Table 3 below, other l-aryl-4-thiatriazines of formula I that were, or may be, prepared in a similar manner are listed in addition to the active ingredients described above: Table 3 *) HPLC / MS conditions: column GROM-SIL 80, ODS.7pH, 4 μm, 40 x 2 mm; flow rate 0.7 ml / min, UV detector.

Example 8 (Compound No. 64) 3- (4-chloro-2-cyclopropyl-6-flurobenzoxazol-7-yl) -1,5-dimethy-6-thioxo- [1,3,5] triazinan-2, 4 -dione (cyclopropyl Rd) A mixture of 370 mg (1.11 mmol) of 3- (3-amino-4-chloro-6-fluoro-2-hydroxyphenyl) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazine-2 , 4-dione and 226 mg (1.67 mmol) of imidomethyl cyclopropanane hydrochloride in 20 ml of methanol (distilled over Na) was stirred for 2 hours at about 20 ° C. The mixture was subsequently concentrated. The residue was quenched in water, whereby the undissolved components were separated and dissolved in ethyl acetate. The ester phase was dried over magnesium sulfate and then concentrated under reduced pressure. This gave 160 mg of the crude product which was purified by column chromatography (mobile phase: cyclohexane / ethyl acetate = 20: 1). Yield: 90 mg (21%); XH NMR oil (400 MHz, in CDC13): d [ppm] = 1.2-1.35 (m, 4H), 2. 2 (m, 1H), 3. 8 (s, 6H), 7. 15 (d, 1H) Precursor 8a 3- (3-amino-4-chloro-6-fluoro-2-hydroxy-enyl) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazinan-2,4-dione 0. 46 g (1.33 mmol) of 3- (3-amino-4-chloro-6-fluoro-2-methoxyphenyl) -1,3-dimethyl-6-thioxo- [1, 3, 5] triazinan-2, 4-dione in 5 ml of methylene chloride was added dropwise at 0 ° C to 8 ml of a 1M solution of boron tribromide in methylene chloride (= 8 mmol BBr3). The reaction mixture was then stirred for two hours at 0 ° C, after which it was stirred slowly in ice water. The valuable product was extracted from the aqueous phase using methylene chloride (twice). The combined organic phases were dried over magnesium sulfate and then concentrated under reduced pressure. This provided 0.21 g (48%) of the value product. The aqueous phase was brought to pH 10 using sodium hydroxide in solution. Then, the mixture was back extracted with methylene chloride. Again, the methylene chloride phases were dried over magnesium sulfate and concentrated. This provided another 0.16 g (36%) of the value product.

Total yield: 84% XH NMR (270 MHz, in CDC13): d [ppm] = 3.8 (s, 6H), 6.9 (d, 1H).

Precursor 8β 3- (3-amino-4-chloro-6-fluoro-2-methoxyphenyl) -1,3-dimethyl-6-thioxo- [1, 3, 5] triazinan-2,4-dione A mixture of 0.22 g (3.98 mmol) of iron powder and 2.5 ml of acetic acid in 5 ml of methanol was heated to reflux temperature. At this temperature, a suspension of 0.50 g (1.33 mmol) of 3- (4-chloro-6-fluoro-2-methoxy-3-nitrophenyl) -1,5-dimethyl-6-thioxo- [1, 3, 5 ] triazine-2,4-dione in 3 ml of methanol was slowly added dropwise to the reaction mixture. The mixture was subsequently stirred for two hours at reflux temperature. After the reaction mixture had been cooled and concentrated, the crude product was filtered on silica gel (mobile phase: ethyl acetate). The filtrate was concentrated under reduced pressure. After drying 0.45 g (98%) of the valuable product was obtained. XH NMR (400 MHz, in CDC13): d [ppm] = 3.75 (s, 3H), 3.8 (s, 6H), 4.05 (bs, 2H), 7.05 (d, 1H).

Precursor 8? 3- (4-chloro-6-fluoro-2-methoxy-3-nitrophenyl) -1,5-dimethyl-6-thioxo- [1,3,5] triazinan-2,4-dione A solution of 3.0 g (15.0 mmol) of diphosgene in 5 ml of toluene was added dropwise at about 20 ° C to a solution of 3.0 g (13.6 mmol) of 4-chloro-6-fluoro-2-methoxy-3 -nitrophenylamine in 15 ml of toluene. Then, the mixture was heated slowly to reflux temperature and stirred for 6 hours at reflux. After the reaction mixture was concentrated and dried, the crude isocyanate was redissolved in 5 ml of toluene for use in the next reaction. 6 ml of triethylamine and a solution of 3.55 g (14.4 mmol) of dimethylthiourea were added dropwise to this solution at approximately 20 ° C. subsequently 4.7 g (28.8 mmol) of carbonyldiimidazole was added to the reaction mixture. The mixture was heated at 80 ° C for 5 hours and then allowed to cool. For the treatment, it was first washed four times with water, then the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude product (6.58 g) was purified by silica gel chromatography (mobile phase: cyclohexane / ethyl acetate = 10: 1). Yield: 1.31 g (24%).

XH NMR (270 MHz, in CDC13): 5 [ppm] = 3.8 (s, 6H), 3.9 (s, 3H), 7.2 (d, 1H).

Precursor 8d 4-chloro-6-fluro-2-methoxy-3-nitrophenylamine A suspension of 40.0 g (152 mmol) of N- (4-chloro-6-fluoro-2-methoxy-3-nitrophenyl) acetamide in 800 ml of 6M hydrochloric acid was heated for 5 hours at reflux temperature, after which the which mixture was stirred overnight at about 20 ° C. For the treatment, the reaction mixture was stirred in ice water. The pH was brought to 8-9 with the addition of a sodium solution [sic]. The mixture was subsequently extracted 6 times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and then concentrated under reduced pressure. Yield: 33 g (98%).

XH NMR (270 MHz, in CDC13): d [ppm] = 3.9 (s, 3H), 4.0 (bs, 2H), 7.0 (d, 1H).

Precursor 8e N- (4-chloro-6-f luoro-2-methoxy-3-nitrofenyl) acetamide A solution of 72.5 g (647 mmol) of NaOSi (CH 3) 3 in 25 ml of tetrahydrofuran was added dropwise at about 20 ° C to a solution of 81 g (323 mmol) of N- (4-chloro-2, 6-difluoro-3-nitro-phenyl) acetamide in 490 ml of dioxane and 50 ml of methanol. The mixture was subsequently heated for two hours at the reflux temperature. After cooling and concentrating, the crude product (black oil) was stirred in 10% strength hydrochloric acid cooled on ice. The resulting product of value was then extracted with ethyl acetate (three times). The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The residue was stirred once with water. The insoluble components were removed and washed three times with water. After drying, 52.1 g were obtained (63%) of the product of value. 2H NMR (270 MHz, in dimethyl sulfoxide d6): d [ppm] = 2.1 (s, 3H), 3.85 (s, 3H), 7.75 (d, 1H), 9.9 (bs, 1H).

Precursor 8? N- (4-chloro-2,6-difluoro-3-nitrophenyl) acetamide . 7 g (487 mmol) of concentrated nitric acid were added dropwise at 0-5 ° C to a solution of 100 g (487 mmol) of N- (4-chloro-2,6-difluorophenyl) acetamide in 500 ml of concentrated sulfuric acid. After the reaction mixture was stirred for one hour at 0-5 ° C, it was stirred in ice water. The resulting solid was separated, washed twice with water and dried. Yield: 81.3 g (72%).

XH NMR (270 MHz in dimethyl sulfoxide d6): d [ppm] = 2.1 (s, 3H), 7.95 (dd, 1H), 10.2 (bs, 1H).

Precursor 8? N- (4-chloro-2,6-difluorophenyl) acetamide 126 g (930 mmol) of sulfuryl chloride were added dropwise at 80 ° C to a solution of 100 g (775 mmol) of difluoroaniline in 700 ml of glacial acetic acid. The mixture was subsequently stirred for 3 hours at 100 ° C. After cooling and concentration, the residue was treated with 200 ml of acetic anhydride. The mixture was then stirred overnight at about 20 ° C. for the treatment, the reaction mixture was stirred in 1.5 1 of ice water. The valuable product was extracted from the aqueous phase using ethyl acetate (three times). The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. Yield: 163 g. lE NMR (270 MHz, in dimethyl sulfoxide d6): d [ppm] = 2.05 (s, 3H), 7.4 (< - \ 2H), 9.8 (bs, 1H).

The following compounds were prepared in the same way: Compound No. 65 3- (4-chloro-6-fluorobenzoxazol-7-yl) -1,5-dimethyl-6-thioxo- [1, 3,5] triazine-2,4-dione (R6 = H; : 209-211 ° C) and Compound No. 66 3- (4-chloro-2-ethyl-6-fluorobenzoxazol-7-yl) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazinan-2,4-dione (R6 = C2H5; p.f .: 156-159 ° C).

Example 9 (Compound No. 67) 3- (4-chloro-6-fluorobenzoxazol-7-yl) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazinan-2,4-dione (R6 = hydrogen) . 0 g (48.1 mmol) of trimethylformamide were added dropwise to a solution of 502 mg (1.50 mmol) of 3- (3-amino-4-chloro-6-fluoro-2-hydroxyphenyl) -1,5-dimethyl-6 -thioxo- [1, 3, 5] -triazine-2,4-dione in 10 ml of methanol. The mixture was then heated to reflux temperature for 9 hours. The reaction mixture was then concentrated under reduced pressure. The resulting crude product was purified by column chromatography (mobile phase: cyclohexane / ethyl acetate = 20: 1). Yield: 240 mg (46%); p.f .: 209-211 ° C.

Compound No. 68 3- (4-chloro-2-ethyl-6-fluorobenzoxazol-7-yl) -1,5-dimethyl-6-thioxo- [1, 3, 5] triazinan-2,4-dione (R6 = ethyl) was prepared in a similar manner.

Examples of use The herbicidal action of l-aryl-4-thiotriazines I was demonstrated by the following greenhouse experiments: The culture vessels that were used were plastic flower pots containing, as a substrate, clay soil with approximately 3.0% humus. The seeds of the test plants were seeded separately for each species. For the pre-emergence treatment, the active ingredients that were suspended or emulsified in water were applied directly after sowing using fine distribution nozzles. The containers were irrigated gently to promote germination and growth and were then covered with translucent plastic hoods until the plans were rooted. This layer causes uniform germination of the test plants, unless this has been adversely affected by the active ingredients. For post-emergence treatment, the test plants were first grown at a height of 3 to 15 cm, depending on the plant's habitat, and only then were they treated with the active ingredients that were suspended or emulsified in water. For this purpose, the test plants were sown directly and grown in the same containers, or first grown separately as seedlings and transplanted to the experimental vessels a few days before treatment. The application rates for the post-emergency treatment were [sic] 125, 62.5, 7.81 and 3.91 g / ha of the active substance (s.a.). The plants were maintained at temperatures of 10-25 ° C or 20-35 ° C, depending on the species. The experimental period lasted for 2 to 4 weeks. During this time, the plants were treated, and their response to individual treatments was evaluated. For the evaluation a scale of 0 to 100 was used. 100 means no emergence of the plants, or complete destruction of at least the aerial parts, while 0 means no damage, or normal growth. The plants used in the greenhouse experiments were composed of the following species: At application rates of 7.81 and 3.91 g / ha of the active substance, the active ingredient No. 30 controlled Amaranthus retroflexus, Chenopodium album, Commelina benghalensis and Setaria faberii considerably better by the post-emergence method compared to compound A At application rates of 125 and 62.5 g / ha of the active substance, the active ingredient No. 39 showed a considerably better herbicidal action against Abutilon theophrasti, Chenopodium album Ipomoea species, Solanum nigrum and Veronica species in the post-emergence method in comparison with compound B.

Claims (4)

CLAIMS A novel l-aryl-4-thiotriazine of the formula I: in which the variables have the following meanings: R is hydrogen, amino, C? -C alkyl or haloalkyl of C _.- C / R is hydrogen, amino, C _-C4 alkyl or C halo-C haloalkyl R is hydrogen or halogen R is cyano or halogen And it's nitrogen, the methino group or, along with R, it's a bridge > C-0-C (R6) = N- R3 is:) hydrogen, hydroxyl, mercapto, nitro, halogen, C? -C6 alkyl, haloalkyl of C? -C6 ) C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkylthio, C 2 -C 6 alkenyloxy, C 2 -C 6 alkenylthio, C 2 -C 6 alkynyloxy or C 2 -C 6 alkynylthio , it being possible, if desired, that each of these eight radicals be linked to one of the following substituents: halogen, cyano, -CO-R8, -CO-OR8 or -CO-N (R8) -R9 ) -CO-R11, -C (RU) (OR13) (OR14), -C (R11) = C (R15) -CO-R16, -CH (R1: 1) -CH (R15) -CO-R15, -CO-OR20, -C (R10) = N-OR7, -N (R21) -R 22 or -CO-N (R 21, -R22) is hydrogen, halogen, Ci-Ce alkyl, C3-Cd alkenyl, C3-Ce alkynyl, C6-C6 alkoxy, C3-C6 alkenyloxy, C-C6 alkynyloxy, C3-Ce cycloalkyl or cycloalkoxy C3-C6, it being possible for each of the 8 radicals mentioned above, if desired, to have 1 to 3 substituents, in each case selected from the group consisting of halogen, C6-C6 alkoxy and -CO-OR8 R is hydrogen, C? -C6 alkyl, Ci-C? Haloalkyl, C3-C6 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, (C6-C6 alkoxy) carbonylalkyl (C? -C6) ) or benzyl R, R8 'independent of each other are: hydrogen, Ci-Ce alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C ?C4 alkyl / C3-C al alkenyl, C3-C6 alkynyl, alkoxy (from C? -C6) -alkyl of C? -C6, (C6-C6 alkoxy) carbonylalkyl of C? -C6, (C3-e alkenyloxy) carbonylalkyl of Ci-C?, phenyl or phenylalkyl of C? -C6 , it being possible that the phenyl group and the phenyl ring of the phenylalkyl group are unsubstituted or have attached to them from 1 to 3 radicals, each selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 alkyl, haloalkyl of Ci-Cß, C-C6 alkoxy and (C? -C6 alkyl) carbonyl R3 is hydrogen or Ci-Cg alkyl R 10 is hydrogen, Ci-Ce alkyl or C Ce alkoxy, it being possible for the last two radicals mentioned to have attached to these one of the following substituents: C 6 -C alkoxy, C 6 -C 6 alkoxycarbonyl or phenoxycarbonyl R11 is hydrogen, C? -C6 alkyl or haloalkyl R13, R14 independently of one another are Ci-Ce alkyl or together are a saturated 2- to 4-membered carbon chain which may be bonded thereto to an alkyl radical of C6-C6 R 15 is hydrogen, cyano, halogen or C? -C6 alkyl R 16 is O-R23 or -N (R21) R22 R20, R23 independent of each other are hydrogen, Ci-Ce alkyl, C6-C6 haloalkyl, C2-C6 alkenyl or C2-C6 alkynyl, it being possible for each of the four groups just mentioned to have attached to it one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, Ci-Cβ alkoxy, C? -C6 alkylthio, (C? -C6 alkyl) carbonyl, (Ci-Ce alkoxy) carbonyl, C? -C6) carbonyloxy, (C3-Ce alkyloxy) carbonyl, (C3-C6 alkynyloxy) carbonyl or phenyl or phenylalkyl of Ci-C?, Where the phenyl rings may be unsubstituted or, in turn, may have attached to these from one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, Ci-Cß alkyl, Cι-C halo haloalkyl, C?-C6 alkoxy and (Ci-Cß alkoxy) carbonyl R _? T, R? _? "independent of each other" are: hydrogen, Ci-Cβ alkyl, C3-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C?-C6 haloalkyl, Ci-Cß alkyloxy-C alquilo alkyl -.- C6, (C?-C6 alkyl) carbonyl, (Ci-Ce) alkoxycarbonyl, (Ci-Ce alkoxy) carbonylalkyl Ci-Cß alkyl or Ci-Cd alkylsulfonyl or R21 and R22 together with the nitrogen-binding atom are a saturated or unsaturated 4- to 7-membered heterocycle which, if desired, may contain one of the following members, in addition to the carbon ring members: -0-, -S-, -N =, -NH- or -N (C? -C6 alkyl) - or a salt for agricultural use of a compound I. The l-aryl-4-thiotriazine of the formula I as claimed in claim 1, wherein Y is nitrogen or the methino group. The l-aryl-4-thiotriazine of the formula I as claimed in claim 1, wherein Y together with R5 is a bridge > C-0-C (R6) = N-. The l-aryl-4-thiotriazine of the formula I as claimed in claim 1, wherein R 5 is hydroxyl, 2) C

1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C

2 -C 6 alkenyloxy, or C 2 alkynyloxy -C6, it being possible that each of these four radicals, if desired, has attached to it one of the following substituents: halogen, cyano, -CO-R8, -CO-OR8 or -CO-N (R8) -R9 . The l-aryl-4-thiotriazine of the formula I as claimed in claim 1, wherein R 5 is mercapto, 2) alktio of C? ~ Ce [sic], cycloalkylthio of C

3-C6, alkenylthio d C2-C6 or alkynylthio of C2-Cd, it being possible that each of these four radicals, if desired, has attached to it one of the following substituents: halogen, cyano, -CO-R8, -CO-OR8 or -CO-N (R8) - R9 The l-aryl-

4-thiotriazine of the formula I as claimed in claim 1, wherein R5 is Ci-Cß alkyl, C?-C6 haloalkyl, 3) -CO-R11, -C (R1: L) (OR13) (OR14), -C (R11) = C (R15) -CO-R16, -CH (Rn) -CH (R15) -CO-R16, -CO-OR20, -C (R10) = N- OR7 or -CO-NÍR '^ - R22. The l-aryl-4-thiatriazine of the formula I as claimed in claim 1, wherein R ~ is hydrogen, nitro, halogen or -N (R21) -R22. The use of an l-aryl-4-thiotriazine of the formula I or of a salt for agricultural use thereof as claimed in claim 1 as a herbicide. A herbicidal composition containing an herbicidally active amount of at least one l-aryl-4-thiotriazine of the formula I or of a salt for agricultural use of I, as claimed in claim 1, and at least one liquid carrier and / or inert solid and, if desired, at least one surfactant. A process for the preparation of active compositions as herbicides consisting of mixing an active amount as a herbicide of at least one l-aryl-4-thiotriazine of the formula I or of a salt for agricultural use of I as claimed in claim 1 , and at least one inert liquid and / or solid carrier and, if desired, at least one surfactant. A method for controlling unwanted vegetation, which consists of allowing an active amount as a herbicide of at least one l-aryl-4-thiotriazine of the formula I or of a salt for agricultural use of I as claimed in claim 1, act on plants, their environment or on seeds. A process for the preparation of an l-aryl-4-thiotriazine of the formula I as claimed in claim 1, wherein the isocyanates of the formula V are reacted with thioureas of formula IV in the presence of an activated form of carbonic acid.