MXPA00005040A - Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives - Google Patents

Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives

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Publication number
MXPA00005040A
MXPA00005040A MXPA/A/2000/005040A MXPA00005040A MXPA00005040A MX PA00005040 A MXPA00005040 A MX PA00005040A MX PA00005040 A MXPA00005040 A MX PA00005040A MX PA00005040 A MXPA00005040 A MX PA00005040A
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Mexico
Prior art keywords
alkyl
halogen
carbonyl
ethyl
butyl
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MXPA/A/2000/005040A
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Spanish (es)
Inventor
Schafer Peter
Hamprecht Gerhard
Menges Markus
Menke Olaf
Reinhard Robert
Zagar Cyrill
Westphalen Karlotto
Otten Martina
Walter Helmut
Elisabeth Heistracher
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Basf Ag 67063 Ludwigshafen De
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Publication of MXPA00005040A publication Critical patent/MXPA00005040A/en

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Abstract

The invention relates to 3-(benzazol-4-yl)pyrimidine-dione-derivatives of formula (I) and the salts thereof, whereby X=O, S;R1=H, NH2, C1-C6-alkyl, C1-C6-alkyl halide;R2=H, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl;R3=H, halogen, C1-C6-alkyl;R4=H, halogen;R5=CN, halogen, C1-C6-alkyl, C1-C6-alkyl halide, C1-C6-alkoxyl, C1-C6-alkoxyl halide;=Y-=a group=N-N(R6)-,=C(ZR7)-N(R6)-,=C(ZR7)-O-,=C(ZR7)-S-;R6=C1-C6-alkyl, C1-C4-alkyl halide, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkyl-SO2, C1-C6-alkyl-CO, C1-C6-alkyl halide-CO, C1-C6-alkyl-CS, C1-C6-alkoxyl-CO, C1-C6-alkoxyl-CS or optionally substituted C1-C6-alkyl;Z=chemical bond, O, S, -S(O)-, -SO2-, -NH-, -N(R8)-;R7, R8=C1-C6-alkyl, C1-C6-alkyl halide, hydroxy-C1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-alkoxyl-C1-C4-alkyl, C1-C4-alkoxyl halide-C1-C4-alkyl, C3-C4-alkenyloxyl-C1-C4-alkyl, C3-C4-alkynyloxyl-C1-C4-alkyl, C3-C8-cycloalkoxyl-C1-C4-alkyl, amino-C1-C4-alkyl, C1-C4-alkylamino-C1-C4-alkyl, di(C1-C4-alkyl)amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylthio halide-C1-C4-alkyl, C3-C4-alkenylthio-C1-C4-alkyl, C3-C4-alkynylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyl, C1-C4-alkylsulfinyl halide-C1-C4-alkyl, C3-C4-alkenylsulfinyl-C1-C4-alkyl, C3-C4-alkynylsulfinyl-C1-C4-alkyl, C3-C6-alkenyl, cyano-C3-C6-alkenyl, C3-C6-alkenyl halide, C3-C6-alkynyl, cyano-C3-C6-alkynyl, C3-C6-alkynyl halide, HO-CO-C1-C4-alkyl, (C1-C4-alkoxyl)CO-C1-C4-alkyl, (C1-C4-alkyl)CS-C1-C4-alkyl, H2N-CO-C1-C4-alkyl, C1-C4-alkyl-NHCO-C1-C4-alkyl, di(C1-C4-alkyl)NCO-C1-C4-alkyl, di(C1-C4-alkyl)phosphonyl-C1-C4-alkyl, optionally substituted C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, 3- to 7-linked heterocyclyl or heterocyclyl-C1-C4-alkyl, whereby each heterocyclyl ring can contain a CO-ring link or CS-ring link, or provided that Z=chemical bond, R7 also H, OH, CN, SH, NH2, halogen, -CH(OH)-CH2-R9, -CH(halogen)-CH2-R9, -CH2-CH(halogen)-R9, -CH=CH-R9 or-CH=C(halogen)-R9, whereby R9=COOH, (C1-C4-alkoxyl)carbonyl, (C1-C4-alkylthio)carbonyl, CONH2, C1-C4-alkyl-NHCO or di(C1-C4-alkyl)NCO, or R7 + R8=an optionally substituted 1,3-propylene-, tetramethylene-, pentamethylene- or ethylene oxyethylene-chain.

Description

Description The present invention relates to novel 3- (benza-zol-4-yl) pyrimidinedione derivatives of the formula I in which the variables have the following meanings: X oxygen or sulfur; R1 hydrogen, amino, C? -C6-alkyl or Cx-Cd-allogenoalkyl; R2 hydrogen, halogen, Ci-Cg-alkyl, C6-haloalkyl, Ci-C-alkylthio, C6-alkylsulfinyl or C6-alkylsulphinyl; R3 hydrogen, halogen or C? -C6 alkyl; R4 hydrogen or halogen; R5 cyano, halogen, C? -C6-alkyl, Cx-Cg-haloalkyl, C? -C6-alkoxy or Ci-Cg-halogenoalkoxy; = Y- one group = N-N (R6) -, = C (ZR7) -N (R6) -, = C (ZR7) -0- or = C (ZR7) -S-; R6 C? -C6-alkyl, C? -C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-alkylsulfonyl, (C? -C6-alkyl) carbonyl, (Ci-Cβ-alkoalkyl) carbonyl, (Ci-Cß-alkyl) thiocarbonyl, (C?-C6-alkoxy) carbonyl, (C?-C6-alkoxy) thiocarbonyl or Ci-Cg-alkyl, which may be substituted by cyano , C? -C6-alkoxy, C? -C6-alkylthio, (C? -C6-alkoxy) carbonyl, (C? -C6-alkylamino) carbonyl, Di (C? -C6-alkyl) aminocarbonyl or (Cx-Ce-alkyl) carbonyloxy; -N (R8) -; R7 and R8 each independently of the other, C? -C6-alkyl, C? -C6-haloalkyl, hydroxy-C? -C4-alkyl, cyano-C1-C4-alkyl, C? -C-alkoxy-C? C 4 -alkyl, C 1 -C 4 -halogenoalkoxy-C?-C 4 -alkyl, C 3 -C 4 -alkenyloxy-C 1 -C 4 -alkyl, C 3 -C -alkynyloxy-C?-C 4 -alkyl, C 3 -C 8 -cycloalkoxy -C? -C4-alkyl, amino-C1-C4-alkyl, C1-C-alkylamino-C? -C4-alkyl, di (C? -C4-alkyl) amino-C? -C -alkyl, C? -C4-alkylthio-C? -C4 -alkyl, C? -C4-haloalkylthio-C? -C4 -alkyl, C3-C4-alkenylthio-C? -C4 -alkyl, C3-C4-alkynylthio-C? -C -alkyl, C? -C- alkylsulfinyl-C? -C4-alkyl, C? -C4-haloalkylsulfinyl-C? -C4-alkyl, C3-C4-alkenylsulfinyl-C? -C -alkyl, C3-C4-alkynylsulfinyl-C? -C4 -alkyl, C? -C4-alkylsulfonyl-C? -C4-alkyl, C? -C4-halogenoalkylsulfonyl-C? -C-alkyl, C3-C4-alkenylsulfonyl-C? -C4-alkyl, C3-C- alkynylsulfonyl-C-C4-alkyl, C3-C6-alkenyl, cyano-C-C6-alkenyl, C-C6-halo-alkenyl, C3-C6-alkynyl, cyano-C3-C6-alkynyl, C3-C6-haloalkynyl, hydroxycarbonyl-C? -C4-alkyl, (C? -C4-alkoxy) carbonyl-C? -C4-alkyl, (C? -C4-alkylthio) carbon-C? -C4-alkyl, aminocarbonyl-C? C4-alkyl, (C? -C4-alkylamino) carbonyl-C? -C4-alkyl, di (C? -C4-alkyl) aminocarbonyl-C? -C4-alkyl, di (C? -C4-alkyl) phosphonyl-C? -C4-alkyl, C3-C8-cycloalkyl, C3-C8-cyc C 4 -C 4 alkyl, phenyl, C 4 -C 4 alkyl, 3 to 7 membered heterocyclyl or heterocyclyl C 1 -C 4 alkyl, each heterocyclyl ring can contain a carbonyl or thiocarbonyl ring member , and each cycloalkyl, phenyl and heterocyclyl ring being unsubstituted or carrying one to four substituents, each selected from the group comprising cyano, nitro, amino, hydroxy, carboxy, halogen, C? -C4-alkyl, C? C -halogenalkyl, C?-C4-alkoxy, C?-C4-haloalkoxy, C?-C4-alkylthio, C?-C4-haloalkylthio, C?-C-alkylsulphinyl, C?-C4-haloalkylsulfonyl, (C C4-alkoxycarbonyl, (C? -C4-alkyl) carbonyl, (C? -C-haloalkyl) carbonyl, (C? -C4-alkyl) carbonyloxy, (C? -C4-haloalkyl) carbonyloxy and di ( C? -C4-alkyl) amino, or, whenever Z means a chemical bond, R7 can mean, if desired, also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH2-R9, CH = C (halogen) -R9 , where R9 means hydroxycarbonyl, (C? -C4-alkoxy) carbonyl, (C? -C4-alkylthio) carbonyl, aminocarbonyl, (C? -C4-alkylamino) carbonyl or di (C? -C-alkyl) aminocarbonyl, or R7 and R8 together form a chain of 1,3-propylene, tetramethylene, penta ethylene or ethyleneoxyethylene, which may in each case be unsubstituted or carry from one to four C? -C4-alkyl groups or one or two groups (C? -C4-alkoxy) carbonyl; as well as the salts useful in the agriculture of the compounds I.
In addition, the invention relates to the use of the compounds I as herbicides, to herbicidal products, which contain the compounds I as active substances, to processes for the preparation of the compounds I and of the herbicidal products using the compounds I. - to processes for combating the growth of undesired plants with the compounds I, as well as - to intermediate products of the formulas III, IV and V for obtaining the compounds I.
In WO 97/08170 certain 3- (benz (ox / ti) azol-7-yl) -6- (trifluoromethyl) -uracils are described as herbicides. Other 3- (benz-thiazol-7-yl) uracils, as well as their use as herbicides and for the desiccation / defoliation of plants are taught in WO 97/08171. The subject of WO 97/12886 are, among other substances, certain 3-benzisoxazol-7-yl-2,4- (lH, 3H) pyrimidinediones, to which a herbicidal and desiccant action is attributed.
The present invention has for its object to provide new uracil compounds with herbicidal action, which allow to fight better and more specifically against undesired plants, than with the known products.
Thus, the present 3- (benza-zol-4-yl) pyrimidinedione derivatives of the formula I were found.
In addition, herbicidal products were found, which contain the compounds I and which have a very good herbicidal action. Additionally, methods for obtaining these compounds and methods for controlling the growth of unwanted plates with compounds I were found.
One or more substances which are present as enantiomeric or diastereomeric mixtures are present. Both the enantiomers or putative diastereomers and their mixtures are subject of the present invention.
For some compounds of the invention, their general formula I represents only one of the possible forms of writing. For example, those compounds with R7 = hydroxy can also be screened with I 'tautomers [-N = C (0H) - < - * - NH-CO-]: Useful salts in agriculture are understood above all to be the salts of those cations or the acid addition salts of those acids whose cations or anions do not negatively affect the herbicidal effect of the compounds I. Thus, as cations they are especially appropriate the ions of the alkali metal salts, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and the salts of transition metals, preferably manganese, copper, zinc and iron, as well as the ammonium anion, which, if desired, it can carry one to four C? -C4 alkyl substituents and / or a phenyl or benzyl substituent, and, if desired, additionally from one to three additional alkyl radicals having 1 to 4 carbon atoms, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, in addition, the phosphonium ions, preferably, tri- (C? -C4-alkyl) -phosphonium, sulfoxonium ions, preferably tri (C? -C4-a) lquil) sulfoxonium.
The anions of suitable acid addition salts are, first, chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, hexafluorosilicate carbonate, hexafluorosate, benzoate, oxalate, dodecylbenzenesulfonate, as well as anions of alkanoic acids with 1 to 4 carbon atoms, preferably the formate, acetate, propionate and butyrate. They can be formed by reacting I with a corresponding anion acid, preferably phosphoric acid and nitric acid.
The organic molecule parts mentioned in the definition of the substituents R1 to R3 and R5 to R9 or as radicals in the cycloalkyl, phenyl or heterocyclic rings represent - the same as the meaning of halogen - collective terms for the individual enumeration of the different members of group. All carbon chains, namely all alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, aminoalkyl, hydroxycarbonylalkyl, aminocarbonylalkyl, phenylalkyl, heterocyclyloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulphonyl, alkenyl, haloalkenyl, cyanoalkenyl, alkenyloxy, alkenylthio, alkenylsulfinyl, alkenylsulfonyl, alkynyl, haloalkynyl, cyanoalkynyl, alkynyloxy, alkynylthio, alkynylsulfinyl and alkynylsulfonyl can be linear or branched. The halogenated substituents preferably have one to five identical or different halogen atoms. Halogen means each time fluorine, chlorine, bromine or iodine.
In addition, they mean, for example: - C -C 4 -alkyl: CH 3, C 2 H 5, CH 2 -C 2 H 5, CH (CH 3) 2, n-butyl, CH (CH 3) -C 2 H 5, CH -CH (CH 3) 2 or C (CH 3) 3; - C? -C4-halogenoalkyl: a C? -C4-alkyl radical such as those mentioned above, which may be partially or completely substituted by fluoro, chloro, bromo and / or iodo, ie, eg CH2F, CHF2, CF3, CH2C1, CH (C1) 2, C (C1) 3, 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, C2Fs, 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; - C? -C6-alkyl: a C? -C4-alkyl radical such as those mentioned above, or, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2.2-? dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpen-1,2-d-methylbutyl, 1,3-d-meth, , - me uo, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably CH 3, C 2 H 5, CH 2 -C 2 H 5, CH (CH 3) 2, n-butyl, C (CH 3) 3, n-pentyl or n-hexyl; - C6C6-halogenoalkyl: a C6C6-alkyl radical such as those mentioned above, which may be partially or completely substituted by fluoro, chloro, bromo and / or iodo, ie, eg one of the radicals mentioned for C?-C4-halogenoalkyl Genannten Substance or für 5-fluoro-l-pentyl, 5-chloro-l-pentyl, 5-bromo-l-pentyl, 5-iodo-l-pentyl, 5,5,5- trichloro-l-penyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-l-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6,6,6-trichloro-l- hexyl or dodecafluorohexyl; - cyano-C? -C4-alkyl: CH2CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanopropyl-1-yl, 1-cyano- but-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, 3- cyanobut-2-yl, 4-cyanobut-2-yl, l- (CH 2 CN) et-1-yl, l- (CH 2 CN) -l- (CH 3) -et-1-yl or l- (CH 2 CN) prop-l-ilo; - hydroxy-C? -C4-alkyl: CH20H, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxyprop-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxybutyl-1-yl, 2-hydroxybutyl-1-yl, 3-hydroxybutyl-yl, 4- hydroxybutyl-1-yl, 1-hydroxybut-2-yl, 2-hydroxybut-2-yl, 3-hydroxybut-2-yl, 4-hydroxybut-2-yl, 1- (CHOH) et-1-yl, 1- (CH 2 OH) -l- (CH 3) -et-l-yl or l- (CH 2 OH) prop-1-yl; C-C-C4-alkyl: CH2NH, 1-aminoethyl, 2-aminoethyl, 1-aminoprop-1-yl, 2-aminoprop-1-yl, 3-aminoprop-1-yl, 1-amino-butyl -1-yl, 2-aminobut-l-yl, 3-aminobut-l-yl, 4-amino-but-1-yl, l-aminobut-2-yl, 2-aminobut-2-yl, 3-amino - but-2-yl, 4-amino-but-2-yl, l- (CH2NH2) et-l-yl, l- (CH2NH2) -l- (CH3) -et-l-yl or 1- (CH2NH2 ) prop-l-ilo; - hydroxycarbonyl-C? -C4-alkyl: CH2C00H, l- (C00H) ethyl, 2- (COOH) ethyl, l- (COOH) prop-l-yl, 2- (COOH) prop-l-yl, 3- (C00H) -prop-l-yl, l- (C00H) but-l-yl, 2- (C00H) but-l-yl, 3- (C00H) but-l-yl, 4- (C00H) but- l -yl, l- (COOH) but-2-yl, 2- (COOH) but-2-yl, 3- (COOH) but-2-yl, 4- (COOH) but-2-yl, l- (CH2C00H) et-l-yl, l- (CH2COOH) -l- (CH3) -et-l-yl or l- (CH2COOH) prop-l-yl; 2- (CONH) et lo, l- (CONH2) prop- - o, - 2 prop- - o, 3- (CONH2) prop-l-yl, l- (CONH2) but-l-yl, 2- ( CONH2) but-l-yl, 3- (CONH2) but-l-yl, 4- (CONH2) but-l-il ?, l- (CONH2) but-2-yl, 2- (CONH2) but-2 -yl, 3- (CONH2) but-2-yl, 4- (CONH2) but-2-yl, l- (CH2CONH2) et-l-yl, l- (CH2CONH2) -1- (CH3) -et- 1-yl or 1- (CH2C0N-H2) prop-1-yl; - phenyl-C? -C4-alkyl: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenyl- but-1-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenyl-but-1-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3- phenyl-but-2-yl, 4-phenylbut-2-yl, 1- (benzyl) -et-l-yl, l- (benzyl) -l- (methyl) -et-l-yl or l- (benzyl) -prop-1-yl, preferably benzyl or 2-phenylethyl; - heterocyclyl-C? -C4-alkyl: heterocyclylmethyl, 1-heterocyclyl-ethyl, 2-heterocyclyl-ethyl, 1-heterocyclyl-prop-1-yl, 2-heterocyclyl-prop-1-yl, 3-heterocyclyl- prop-l-yl, 1-heterocyclyl-but-1-yl, 2-heterocyclyl-but-l-yl, 3-heterocyclyl-but-l-yl, 4-heterocyclyl-but-l-yl, l-heterocyclyl- but-2-yl, 2-heterocyclyl-but-2-yl, 3-heterocyclyl-but-2-yl, 3-heterocyclyl-but-2-yl, 4-heterocyclyl-but-2-yl, l- (heterocyclylmethyl) -et-1-yl, 1- (heterocyclylmethyl) -l- (methyl) -et-1-yl or 1- (heterocyclylmethyl) -prop-1-yl, preferably heterocyclylmethyl or 2-heterocyclyl -ethyl; C -C4-alkoxy for: 0CH3, OC2H5, OCH2-CH5, OCH (CH3) 2, n-butoxy, OCH (CH3) -C2H5, OCH2-CH (CH3) 2 or C (CH3) 3, preferably 0CH3, OC2H5 O OCH (CH3) 2; - C? -C4-halogenoalkoxy: a C? -C4-alkoxy radical such as those mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz., Eg 0CH2F, OCHF2, OCF3 , 0CH2C1, OCH (Cl) 2, 0C (C1) 3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy , 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2, 2,2-trichloroethoxy, OC2Fs, 2-fluoropropoxy, 3-fluoropropoxy , 2, 2-difluoropropoxy, 2, 3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3, 3, 3-trifluoropropoxy, 3,3,3 -trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1- (CH2F) -2-fluoroethoxy, l- (CH2Cl) -2-chloroethoxy, l- (CH2Br) -2-bromoethoxy, 4-fluoro-butoxy, 4-chlorobutoxy , 4-bromobutoxy or nonafluorobutoxy, prefetoxy or 2,2,2-trifluoroethoxy; C? -C6-alkoxy: a C? -C4-alkoxy radical such as those mentioned above, or for example n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methyl-butoxy, 2,2-dimethylpropoxy, -ethylpropoxy, n-hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethyl-butoxy , 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-tri-methylpropoxy, 1,2,2 -trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy, preferably OCH 3, OC 2 H 5, OCH 2 -C 2 H 5, OCH (CH 3) 2, n-butoxy, OC (CH 3) 3, n-pentoxy or n- hexoxi; C? -C6-halogenoalkoxy: a C? -C6-alkoxy radical such as those mentioned above, which may be partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, for example, one of the radicals mentioned for C? -C4-halogenoalkoxy or for 5-fluoro-l-pentoxy, 5-chloro-l-pentoxy, 5-bromo-l-pentoxy, 5-iodo-l-pentoxy, 5,5,5-trichloro-l -pentoxy, undecafluoropen-toxi, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6-trichloro-1-hexoxy or dsdecafluorohexoxi; C? -C -alkylthio: SCH3, SC2H5, SCH2-C2H5, SCH (CH3) 2, n-butylthio, SCH (CH3) -C2H5, SCH2-CH (CH3) 2 or SC (CH3) 3, preferably SCH3 or SC2H5; C? -C4-haloalkylthio: a C? -C4-alkylthio radical such as those mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg SCH2F, SCHF2, SCF3, SCH2C1, SCH (C1) 2, SC (Cl) 3, chlorofluoromethylthio, dichloro-fluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, SC2F5, 2-fluoropropylthio, 3-fluoropro- pylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloro-propylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3, 3,3-tri-chloropropylthio, SCH2-C2F5, SCF2-C2F5, 1- (CH2F) -2-fluoroethylthio, 1- (CH2Cl) -2-chloroethylthio, 1- (CH2Br) -2-bromoethylthio, 4-fluorobu- tiltium, 4-chlorobutylthio, 4-bromobutylthio or SCF -CF2-C2F5, preferably SCHF2, SCF3, dichlorofluoromethylthio, chlorodifluoromethylthi or or 2, 2, 2-trifluoroethylthio; c onados, or e. n-pent t o, -met u t o, -me u-thio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpenthylthio, 1,1-dimethylbutylthio, 1,2 dimethyl butylthio, 1,3-dimethyl butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1-trimethylpro-pylthio, 1 , 2,2-trimethylpropylthio, 1-ethyl-l-methylpropylthio or l-ethyl-2-methylpropylthio, preferably SCH3, SC2H5, SCH-C2H5, SCH (CH3) 2, n-butylthio, SC (CH3) 3, n- pentthylthio or n-hexylthio; C 4 -C-alkoxy-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl substituted by C 4 -C-alkoxy -as the above-mentioned, namely, eg für CH 2 -OCH 3, CH 2 -CH 2 H 5 , n-propoxymethyl, CH2-OCH (CH3) 2, n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH2-OC (CH3) 3, 2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (n-pro-poxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2- methylpropoxy) ethyl, 2- (1,1-di-ethyl-toxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (n-pro-poxy) 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, - (ethoxy) -propyl, 3- (n-propoxy) propyl, 3- (1-methylethoxy) propyl, 3- (n-bu-toxy) propyl, 3- (1-methylpropoxy) ropyl, 3- (2- methylpropoxy) pro-phenyl, 3- (1,1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, - (n-butoxy) butyl, 2- (l-methylpropoxy) butyl, 2- (2-methylpro-poxy) butyl, 2- (1, 1- dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (n-butoxy) util, 3- (1- methylpropoxy) butyl, 3- (2-methylpro-poxy) butyl, 3- (1,1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (ethoxy) butyl, 4- (n-propoxy) butyl, - (1-methylethoxy) butyl, 4- (n-butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpro-poxy) butyl or 4- (1, 1-dimethylethoxy) butyl, preferably CH 2 -OCH3, CH2-OC2H5, 2- (0CH3) ethyl or 2- (OC2H5) ethyl; C? -C4-halogenoalkoxy-C? -C4-alkyl: C? -C4-alkyl substituted by C? -C -haloalkoxy as the above-mentioned, viz. ex. 2- (OCHF2) ethyl, 2- (OCF3) ethyl or 2- (OC2F5) ethyl; C? -C4-alkylthio-C? -C -alkyl: C? -C4-alkyl substituted by C? -C4-alkylthio- as mentioned above - namely, eg CH2-SCH3, CH2-SC2H5, n-propylthiomethyl, CH2-SCH (CH3) 2, n-butyl-thiomethyl, (l-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH2-SC (CH3) 3, 2- (methylthio) ethyl, 2- ( ethylthio) -ethyl, 2- (n-pro-pylthio) ethyl, 2- (l-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (l, l-dimethylethyl) o lo, 2- ( met to) prop or, - e -thio) propyl, 2- (n-propylthio) propyl, 2- (1-methylethylthio) propyl, 2- (n-butylthio) propyl, 2- (1-methylpropylthio) propyl, - (2-methyl-propylthio) ropyl, 2- (1,1-dimethylethylthio) ropyl, 3- (methyl-thio) propyl, 3- (ethylthio) propyl, 3- (n-propylthio) propyl, 3- (1 -methylethylthio) propyl, 3- (n-butylthio) propyl, 3- (l-methyl-propylthio) -propyl, 3- (2-methylpropylthio) propyl, 3- (1,1-dimethyl-ethylthio) propyl, 2- (methylthio) butyl, 2- (ethylthio) butyl, 2- (n-propylthio) butyl, 2- (1-methylethylthio) butyl, 2- (n-butylthio) butyl, 2- (1-methylpropylthio) butyl, 2- (2-methylpropylthio) buti lo, 2- (1, 1-dimethylethylthio) butyl, 3- (methylthio) butyl, 3- (ethylthio) butyl, 3- (n-propylthio) butyl, 3- (1-methylethylthis) butyl, 3-. { n-butylthio) butyl, 3- (1-methylpropylthio) butyl, 3- (2-methylpropylthio) butyl, 3- (1,1-dimethylethylthio) butyl, 4- (methylthio) butyl, 4- (ethylthio) butyl, - (n-propylthio) butyl, 4- (l-methylethylthio) butyl, 4- (n-butylthio) -butyl, 4- (1-methylpro-pylthio) butyl, 4- (2-methylpropylthio) utilo or 4- ( 1, 1-dimethylethylthio) butyl, preferably CH2-SCH3, CH2-SC2H5, 2- (SCH3) ethyl or 2- (SC2H5) ethyl; C?-C4-haloalkylthio-C?-C4-alkyl: C?-C4-alkyl substituted by C?-C4-haloalkylthio as the above-mentioned, namely, eg 2- (SCHF 2) ethyl, 2- ( SCF3) ethyl or 2- (SC2F5) ethyl; (C? -C4-alkyl) carbonyl: C0-CH3, C0-C2H5, CO-CH2-C2H5, CO-CH (CH3) 2, n-butylcarbonyl, CO-CH (CH3) -C2H5, CO-CH2-CH (CH3) 2 < CO-C (CH3) 3, preferably C0-CH3 or CO-C H5; (C? -C4-haloalkyl) carbonyl: a radical (C? -C-alkyl) carbonyl - such as those mentioned above - which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz. C0-CH2F, C0-CHF2, C0-CF3, C0-CH2C1, C0-CH (C1) 2, C0-C (C1) 3, chlorofluoromethylcarbonyl, dichlorofluoroethylcarbonyl, chloro-difluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl bonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-di-chloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, CO-C2F5, 2 -fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl , 3,3, 3-trichloropropylcarbonyl, CO-CH2-C2F5, CO-CF2-C2F5, 1- (CH2F) -2-fluoroethylcarbonyl, 1- (CH2Cl) -2-chloroethylcarbonyl, 1- (CH2Br) -2-bromoethylcarbonyl , 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcar-CO-CH2Cl or 2, 2, 2-trifluoroethylcarbonyl; (C? -C6-alkyl) carbonyl: one of the above-mentioned radicals (C? -C-alkyl) -carbonyl, or, for example, n-pentyl-CO, 1-methylbutyl-CO, 2-methylbutyl-CO , 3-methylbutyl-CO, 2, 2-dimethylpropyl-CO, 1-ethylpropyl-CO, n-hexyl-CO, 1,1-dimethylpropyl-CO, 1,2-dimethyl-propyl-CO, 1-methylpentyl-CO , 2-methylpentyl-CO, 3-methylpentyl-CO, 4-methylpentyl-CO, 1, 1-dimethylbutyl-CO, 1, 2-dimethylbutyl-CO, 1,3-dimethylbutyl-CO, 2,2-dimethylbutyl-CO , 2, 3-dimethylbutyl-CO, 3,3-dimethylbutyl-CO, 1-ethylbutyl-CO, 2-ethylbutyl-CO, 1,1,2-tri-methylpropyl-CO, 1,2,2-trimethylpropyl-CO , 1-ethyl-l-methylpropyl-CO or l-ethyl-2-methylpropyl-C0, preferably CO-CH3, CO-C2H5, CO-CH2-C2H5, CO-CH (CH3) 2, n-butyl-CO, CO-C (CH3) 3, CO- (n-C5H ??) or CO- (n-C6H? 3); (C? -C6-haloalkyl) carbonyl: a (C? -C6-alkyl) carbonyl radical - such as those mentioned above - which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz. C0-CH2F, C0-CHF2, C0-CF3, C0-CH2C1, C0-CH (C1) 2, CO-C (Cl) 3, chlorofluoromethylcarbonyl, dichlorofluoromethylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, -bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-di-chloro-2-fluoroethylcarbonyl , 2,2, 2-trichloroethylcarbonyl, CO-C2F5, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2 -bromopropylcarbonyl, 3-bromopropylcarbonyl, 3, 3, 3-trifluoropropylcarbonyl, 3,3, 3-trichloropropylcarbonyl, CO-CH2-C2F5, CO-CF2-C2F5, 1- (CH2F) -2-fluoroethylcarbonyl, 1- (CH2C1) -2-chloroethylcarbonyl, 1- (CH2Br) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl, preferably C0-CF3CO-CH2Cl or 2,2,2-trifluoroethylcarbonyl; (C1-C4-alkyl) carbonyloxy: 0-C0-CH3, 0-CO-C2H5, 0-CO-CH2-C2H5, 0-CO-CH (CH3) 2, 0-CO-CH2-CH2-C2H5, O -CO-CH (CH3) -C H5, O-CO-CH2-CH (CH3) 2 or 0-CO-C (CH3) 3, preferably 0-C0-CH3 or 0-CO-C2H5; (C? -C4-haloalkyl) carbonyloxy: a radical (C? -C-alkyl) carbonyl - as mentioned above - which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, viz. .ej. 0-CO-CH2F, 0-CO-CHF2, 0-CO-CF3, 0-CO-CH2Cl, 0-CO-CH (Cl) 2, 0-C0-C (Cl) 3, chlorofluoromethylcarbonyloxy, dichlo - - luoroet lcar on ox, -c oroe car on ox, - romoe -carbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, -chloro-2, 2-difluoroethylcarbonyloxy, 2,2-di-chloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, 0-CO-C2F5, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy , 2, 3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bro-mo-propylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, 0-CO -CH2-C2F5, 0-CO-CF2-C2F5, 1- (CH2F) -2-fluoroethylcarbonyl oxy, 1- (CH2C1) -2-chloroethylcarbonyloxy, 1- (CH2Br) -2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nona-fluorobutylcarbonyloxy, preferably 0-C0-CF3, 0-CO -CH2Cl or 2,2, 2-trifluoroethylcarbonyloxy; (C? -C6-alkyl) carbonyloxy: one of the above-mentioned radicals (C? -C4-al-quil) carbonyloxy, or, for example, n-pentyl-COO, 1-methylbutyl-COO, 2-methylbutyl-C00, 3-methylbutyl-COO, 2,2-dimethyl-propyl-COO, 1-ethylpropyl-COO, n-hexyl-COO, 1,1-dimethylpro-pil-COO, 1,2-dimethylpropyl-COO, 1-methylpentyl-COO, 2-methylpen-tyl-COO, 3-methylpentyl-COO, 4-methylpentyl-COO, 1,1-dimethylbutyl-COO, 1,2-dimethylbutyl- COO, 1,3-dimethylbutyl-COO, 2,2-dimethyl-butyl-COO, 2,3-dimethylbutyl-COO, 3,3-dimethylbutyl-COO, 1-ethylbutyl-COO, 2-ethylbutyl-COO, 1, 1,2-trimethylpropyl-COO, 1,2,2-trimethylpropyl-COO, 1-ethyl-l-methylpropyl-COO or l-ethyl-2-methylpropyl-C00, preferably 0-CO-CH3, 0-CO-C2H5 , 0-CO-CH2-C2H5, 0-CO-CH (CH3) 2, n-butyl-COO, 0-CO-C (CH3) 3, 0-C0- (n-C5H?) Or 0-CO- (n-C6H? 3); (C? -C6-alkyl) thiocarbonyl: CS-CH3, CS-C2H5, CS-CH2-C2H5, CS-CH (CH3) 2, CS- (n-C4H9), CS-CH (CH3) -C2H5, CS -CH2-CH (CH3) 2, CS-C (CH3) 3, CS- n-CsHx), CS-CH (CH3) -CH2-C2H5, CS-CH2-CH (CH3) -C2H5, CS-CH CH2 -CH (CH3) 2, CS-C (CH3) 2-C2H5, CS-CH (CH3) -CH (CH3) 2, CS-CH2-C (CH3) 3, CS-CH (C2H5) -C2H5, CS - (n-C6H13), CS-CH (CH3) - (n-C4H9), CS-CH2-CH (CH3) -CH2-C H5, CS-CH2CH2-CH (CH3) -C H5, CS-CH2CH2CH2- CH (CH3) 2, CS-C (CH3) 2-CH2-C2H5, CS-CH (CH3) -CH (CH3) -C2H5, CS-CH (CH3) -CH2-CH (CH3) 2, CS-CH2 -C (CH3) 2-C2H5, CS-CH2-CH (CH3) -CH (CH3), CS-CH2CH2-C (CH3) 3, CS-CH (C2H5) -CH2-C2H5, CS-CH-CH ( C2H5) -C2H5, CS-C (CH3) 2-CH (CH3) 2, CS-CH (CH3) -C (CH3) 3, CS-C (CH3) (C2H5) -C2H5 or CS-CH (C2H5) -CH (CH3) 2, preferably CS-CH3, CS-C2H5, CS-CH2-C2H5 / CS-CH (CH3) 2 O CS- (n-C4H9); C -OCH CH 3) 2, n-butoxy car on or, - 3 - 2 5, CO-OCH 2 -CH (CH 3) 2 or CO-OC (CH 3) 3, preferably CO-OCH 3 or C 0 - OC 2 H 5; - (C? -C6-alkoxy) carbonyl: one of the above-mentioned radicals (C? -C4-alkoxy) carbonyl, or, for example, n-pentoxy-CO, 1-methylbutoxy-CO, 2-methylbutoxy-? CO, 3-methylbutoxy-CO, 2,2-dimethylpropoxy-CO, 1-ethylpropoxy-CO, n-hexoxy-CO, 1,1-dimethylpropoxy-CO, 1,2-dimethylpropoxy-CO, 1-methylpentoxy- CO, 2-methylpentoxy-CO, 3-methyl-pentoxy-CO, 4-methylpentoxy-C0, 1, 1-dimethylbutoxy-CO, 1,2-dimethylbutoxy-CO, 1,3-dimethylbutoxy-CO, 2, 2-dimethylbutoxy-CO, 2,3-dimethylbutoxy-CO, 3,3-dimethylbutoxy-CO, 1-ethylbutoxy-CO, 2-ethylbutoxy-C0, 1, 1, 2-trimethylpropoxy-C0, 1,2,2- trimethylpropoxy-CO, 1-ethyl-l-methylpropoxy-CO or l-ethyl-2-methylpropoxy-CO, preferably C0-0CH3, CO-OC2H5 / CO-OCH2-C2H5, CO-OCH (CH3) 2, n -butoxy-CO, CO-OC (CH3) 3, n-pentoxy-CO or n-hexoxy-CO; - (C? -C4-alkoxy) carbonyl-C? -C4-alkyl: C? -C4-alkyl substituted by (C? -C4-alkoxy) -carbonyl - as mentioned above - namely, eg. CH2-CO-OCH3, CH2-CO-OC2H5, CH2-CO-OCH2-C2H5, CH2-CO-OCH (CH3) 2, n-butoxycarbonylmethyl, CH2-CO-OCH (CH3) -C2H5, CH2-C0-OCH2 -CH (CH3) 2, CH2-CO-OC (CH3) 3, 1- (CO-OCH3) ethyl, l- (CO- 0C2H5) ethyl, l- (CO-OCH2-C2H5) ethyl, 1- [CH (CH3) 2] ethyl, l- (n-butoxycarbonyl) ethyl, l- [1-methylpropoxycarbonyl] ethyl, l- [2-methylpropoxycarbonyl] ethyl, 2- (CO-OCH3) ethyl, 2- ( CO-OC2H5) ethyl, 2- (CO-OCH2-C2H5) ethyl, 2- [CO-OCH (CH3) 2 Jetyl, 2- (n-butoxycarbonyl) ethyl, 2- [1-methylpropoxycarbonyl-Jetyl, 2- [2-methylpropoxycarbonyl] ethyl, 2- [CO-OC (CH3) 3 Jetyl, 2- (CO-OCH3) propyl, 2- (CO-OC2H5) propyl, 2- (CO-OCH2-C2H5) propyl? , 2- [C0- OCH (CH) 2 J-propyl, 2- (n-butoxycarbonyl) ropyl, 2- [1-methylpropoxycarbonyl] propyl, 2- [2-methylpropoxycarbonyl] propyl, 2- [CO- OC (CH3 ) 3 Jpropyl, 3- (CO-OCH3) -propyl, 3- (CO-OC2H5) propyl, 3- (CO-OCH2-C2H5) -propyl, 3- [CO-OCH (CH3) 2 Jpr opyl, 3- (n-butoxycarbonyl Jpropyl, 3- [1-methylpropoxycarbonyl] Jpropyl, 3- [2-methylpropoxycarbonylpropyl], 3- [CO-OC (CH3) 3 J-propyl, 2- (CO-OCH3) butyl, 2- (CO- OC2H5) butyl, 2- (CO-OCH2-C2H5) butyl, 2- [CO-OCH (CH3) 2 J- butyl, 2- (n-butoxycarbonyl) butyl, 2- [1-methylpropoxycarbonylbutyl, 2- [2-methylpropoxycarbonylJbutyl, 2- [C0-OC (CH3) 3Jbutyl, 3- (C0-0CH3) butyl, 3- (CO-OC2H5) butyl, 3- (CO-OCH2-C2H5) butyl, 3- [ CO-OCH (CH3) 2Jbutyl, 3- (n-butoxycarbonyl) butyl, 3- [1-methylpropoxycarbonyl] butyl, 3- [2-methylpropoxycarbonyljbutyl, 3- [CO-OC (CH3) 3Jbutyl, 4- (CO-OCH3) butyl, 4- (CO-OC2H5) butyl, 4- (CO-OCH2-C2H5) butyl, 4- [C0-0CH (CH3) 2 Jbutyl, 4- (n-butoxycarbonyl) butyl, 4- [1-methylpropoxycarbonyl Jbu-] CH2-CO-OCH3, CH2-CO-OC2H5, 1- (C0-0CH3 Jet or 1- (C0-0C2H5 Jetyl; - (C? -C6-alkoxy) thiocarbonyl: eg CS-0CH3, CS-0C2H5, CS-0CH2-C2H5, CS-0CH (CH3) 2, CS-0 (n-C4H9), CS-OCH ( CH3) -C2H5, CS-0CH2-CH (CH3) 2, CS-0C (CH3) 3, CS-O (n-C5H), CS-OCH (CH3) -CH2-C2H5, CS-OCH2-CH (CH3) -C2H5, CS-0CH2CH2-CH (CH3) 2, C0-0CH2-C (CH3) 3, CS-OCH (C2H5) -C2H5, CS-0 (n-C6H13), CS-OC (CH3) 2-C2H5, CS-OCH (CH3) -CH (CH3) 2, CS-OCH (CH3) - (n-C4H9), CS-0CH2-CH (CH3) -CH2-C2H5, CS-OCH2CH2-CH (CH3 ) -C-H5, CS-OCH2CH2CH2-CH (CH3) 2, CS-OC (CH3) 2-CH2-C2H5, CS-OCH (CH3) -CH (CH3) -C2H5, CS-OCH (CH3) -CH2- CH (CH3) 2, CS-0CH2-C (CH3) 2-C2H5, CS-OCH2-CH (CH3) -CH (CH3) 2, CS-OCH2CH2-C (CH3) 3, CS-OC (C2H5) - CH2-C2H5, CS-OCH2-CH (C2H5) -C2H5, CS-OC (CH3) 2-CH (CH3) 2, CS-OCH (CH3) -C (CH3) 3, CS-OC (CH3) (C2H5) -C2H5 or CS-OCH (C2H5) -CH (CH3) 2, preferably CS-OCH3 or CS-OC2H5; - (C? -C4-alkylthio) carbonyl: C0-SCH3, CO-SC2H5, CO-SCH2-C2H5, CO- SCH (CH3) 2, CO-SCH2CH2-C2H5, C0-SCH (CH3) -C2H5, CO- SCH2-CH (CH3) 2 O CO-SC (CH3) 3, preferably CO-SCH3 or CO-SC2H5; (C? -C-alkylthio) carbonyl-C? -C4-alkyl: C? -C4-alkyl substituted by (C? -C4-alkylthio) carbonyl - such as those mentioned above, namely, eg CH2- CO-SCH3, CH2-CO-SC2H5, CH2-CO-SCH2-C2H5, CH2-CO-SCH (CH3) 2, CH2-CO-SCH2CH2-C2H5, CH2-CO-SCH (CH3) -C2H5, CH2-CO -SCH2-CH (CH3) 2, CH2-CO-SC (CH3) 3, 1- C0-SCH3) ethyl, l- (CO-SC2H5 Jetyl, l- (CO-SCH2-C2H5) ethyl, 1- CO-SCH (CH3) 2 Jetyl, 1- (CO-SCH2CH2-C2H5) ethyl, 1- CO-SCH (CH3) -C2H5 J ethyl, 1- [CO-SCH2-CH (CH3) 2] ethyl, 1- CO-SC (CH 3) 3 Jethyl, 2- (CO-SCH 3) ethyl, 2- (CO-SC 2 H 5) ethyl, 2- CO-SCH2-C2H5) ethyl, 2- [CO-SCH (CH3) 2 Jetyl, 2- CO-SCH2CH2-C2H5) ethyl, 2- [CO-SCH (CH3) -C2H5 Jetyl, 2- CO-SCH2 -CH (CH3) 2] ethyl, 2- [CO-SC (CH3) 3 Jetyl, 2- (CO-SCH3J-propyl, 2- (CO-SC2H5) propyl, 2- (CO-SCH2-C2H5 Jpropyl, 2 - CO-SCH (CH3) 2 Jpropyl, 2- (CO-SCH2CH2-C2H5) propyl, 2- CO-SCH (CH3) -C2H5 jpropyl, 2- [C0-SCH2-CH (CH3) 2 Jpropyl, 2- CO -SC (CH3) 3 Jpropyl, 3- (CO-SCH3) propyl, 3- (CO-SC2H5 Jpropyl, 3- CO-SCH2-C2H5 Jpropyl, 3- [CO-SCH (CH3) 2 Jpropyl, 3- CO-SCH2CH2-C2H5) propyl, 3- [CO-SCH (CH3) -C2H5 Jpropyl, 3- CO-SCH2- CH (CH3) 2 Jpropyl, 3- [CO-SC (CH3) 3 J-propyl, 2- C0-SCH3) butyl, 2- (CO-SC2H5) butyl, 2- (CO-SCH2-C2H5) butyl, 2- CO-SCH (CH3) 2 J butyl, 2- (CO-SCH2CH2-C2H5) butyl, 2- CO-SCH (CH3) -C2H5] butyl, 2- [CO-SCH2-CH (CH3) 2 Jbutyl, 2- CO-SC (CH3) 3Jbutyl, 3- (CO-SCH3) butyl, 3- (CO-SC2H5) butyl, 3- CO-SCH2-C2H5) butyl, 3- [CO-SCH (CH3) 2 Jbutyl, 3- CO-SCH2CH2-C2H5) butyl, 3- [CO-SCH (CH3) -C2H5] butyl, CH3) - ut lo, 4- (CO-SC2H5) uo, - - 2- 2 5 uo, 4- [CO-SCH (CH3J2] butyl ?, 4- (CO-SCH2CH2-C2H5) butyl, 4- [CO-SCH (CH3 ) -C2H5Jbutyl, 4- [CO-SCH2-CH (CH3) 2 Jbutyl or 4- [CO-SC (CH3) 3Jbutyl, preferably CH2-CO-SCH3, CH2-CO-SC2H5, 1- (C0-SCH3 Jetyl or 1- (CO-SC2H5) ethyl; - C6C-alkylsulfinyl: a C? -C -alkylsulfinyl radical, such as, for example, SO-CH3, SO-C2H5, SO-CH2-C2H5, SO-CH (CH3) 2, SO- (n-C4H9) ), SO-CH (CH3) -C2H5, SO-CH-CH (CH3) 2 or SO-C (CH3) 3, or eg SO- (n-C5H ??), 1-methylbutyl-SO, 2-methylbutyl-SO, 3-methylbutyl-SO, 2,2-dimethylpropyl-SO, 1-ethylpropyl-SO, n-hexyl-SO, 1,1-dimethylpropyl-SO, 1,2-dimethylpropyl-SO, 1-methylpentyl-SO, 2-methylpentyl-SO, 3-methylpentyl-SO, 4-methylpentyl-SO, 1,1-dimethylbutyl-SO, 1,2-dimethylbutyl-SO, 1,3-dimethylbutyl- SO, 2,2-dimethylbutyl-SO, 2,3-dimethylbutyl-SO, 3,3-dimethylbutyl-SO, 1-ethyl-butyl-SO, 2-ethylbutyl-SO, 1, 1, 2-trimethylpropyl- SO, 1,2,2-trimethylpropyl-SO, 1-ethyl-1-methylpropyl-SO or 1-ethyl-2-methylpropyl-SO, preferably S0-CH3 / SO-C2H5, SO-CH2-C2H5, SO -CH (CH3), SO- (n-C4H9), SO-C (CH3) 3, SO- (n-C5H ??) or S0- (n-C6H13); -C 1 -C 4 -Cylsulfinyl-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl substituted by C 1 -C 4 -alkylsulfinyl, such as those mentioned above, namely, eg CH 2 SOCH 3, CH 2 SOC 2 H 5, n-propylsulfinylmethyl, CH 2 SOCH (CH 3) 2, n-butylsulfinylmethyl, (1-methylpropylsulfinyl) methyl, (2-methylpropylsulfinyl) methyl, (1,1-dimethylethylsulfinyl) -methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2- (n- propylsulfinyl) ethyl, 2- (1-methylethylsulfinyl) ethyl, 2- (n-butylsulfinyl) ethyl, 2- (1-methylpropylsulfinyl) Jetyl, 2- (2-methylpropylsulfinyl) ethyl, 2- (1, 1-dimethylethylsulfinyl) ethyl, 2- (S0CH3 Jpropyl, 3- (S0CH3) Jpropyl, 2- (SOC2H5) -propyl, 3- (SOC2H5Jpropyl, 3- (propylsulfinyl) propyl, 3- (butylsulfinyl) propyl, 4- (S0CH3) butyl, 4- (SOC2H5) butyl, 4- (n-propylsulfinyl) butyl or 4- (n-butylsulfinyl) butyl, especially für 2- (SOCH3) ethyl; C 1 -C 4 -haloalkylsulfinyl-C 1 -C -alkyl: C 1 -C 4 -alkyl substituted by C 1 -C 4 -haloalkylsulfinyl, such as those mentioned above, viz. 2- (2, 2, 2- trifluoroethylsulfinyl) -ethyl; C? -C4-alkylsulfonyl: S02-CH3, S02-C2H5, S02-CH2-C2H5, S02-CH (CH3) 2, n-butylsulfonyl, S02-CH (CH3) -C2H5, S02-CH2-CH (CH3 ) 2 or S02-C (CH3) 3, preferably S02-CH3 or S02-C2H5; - is preferably substituted by fluoro, chloro, bromo and / or iodo, namely, eg S02-CH2F, S02-CHF2, S02-CF3, S02-CH2C1, S02-CH (C1) 2, S02-C (C1) 3, chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulphonyl, S02-C2F5, 2-fluoropropylsulfonyl, 3- fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dichloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3, 3,3-trichloropropylsulfonyl, S02-CH2-C2F5 / S02-CF2-C2F5, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2- bromoethylsulfonyl, 4-fluoro butylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl, preferably S02-CH2C1, S02-CF3 or 2,2,2-trifluoroethylsulfonyl; - Cx-Cd-alkylsulfonyl: a C? -C4-alkylsulfonyl radical such as those mentioned above, or for example S02- (n-CsH ??), l-methylbutyl-S02, 2-methylbutyl-S02, 3-methylbutyl -S02, 2,2-dimethylpropyl-S02, l-ethylpropyl-S02, n-hexyl-S02, 1, l-dimethylpropyl-S02, 1,2-dimethylpropyl-S0, l-methylpentyl-S02, 2-methylpentyl -S02, 3-methyl-pentyl-S02, 4-methylpentyl-S02, 1, l-dimethylbutyl-S02, 1,2-dimethylbutyl-S02 / l, 3-dimethylbutyl-S02, 2, 2-dimethylbutyl-S02 , 2,3-dimethylbutyl-S02, 3,3-dimethylbutyl-S02, l-ethylbutyl-S02, 2-ethylbutyl-S02, 1, 1, 2-trimethylpropyl-S02, 1,2,2-trimethylpropyl-S02 , l-ethyl-l-methylpropyl-S02 or l-ethyl-2-methylpropyl-S02, preferably S02-CH3, S02-C2H5, S02-CH2-C2H5, S02-CH (CH3) 2, S02- (n-C4H9 ), S02-C (CH3) 3, S02- (n-C5H ??) or S02- (n-C6H? 3); - C 1 -C 4 -alkylsulfonyl-C?-C 4 -alkyl: C?-C 4 -alkyl substituted by C?-C 4 -alkylsulfonyl as mentioned above, namely, eg CH 2 S0 2 -CH 3, CH 2 S0 2 -C 2 H 5, CH 2 S0 2 -CH2-C2H5, CH2S02-CH (CH3) 2, CH2S0 -CH2CH2-C H5, (l-methylpropylsulfonyl) methyl, (2-methylpropylsulfonylmethyl, CH2S02-C (CH3) 3, CH (CH3) S02-CH3, CH (CH3) S02-C2H5, CH2CH2S02-CH3, CH2CH2S02-C2H5, CH2CH2S02-CH2-C2H5, CH2CH2S02-CH (CH3) 2, CH2CH2S02-CH2CH2-C2H5, 2- (1-methylpropyl-sulphonyl) ethyl, 2- ( 2-Methylpropylsulfonyl) ethyl, CH2CH2S02-C (CH3) 3, 2- (S02-CH3) Jpropyl, 2- (S02-C2H5) J-propyl, 2- (S02-CH2-C2H5-J-propyl, 2- [S02-CH (CH3) 2 -propyl , 2- (S02-CH2CH2-C2H5) J-propyl, 2- (l-methyl-propylsulfonyl-J-propyl, 2- (2-methyl-propylsulfonyl-J-propyl, 2- [S02-C (CH3) 3-Jpropyl, 3- (S02-CH3-Jpropyl, 3- (S02-C2H5) propyl, - 2- H2 H2- 2 5 prop or, - -me prop prop prop, 3- (2-Methylpropylsulfonyl) ropyl, 3- [S02-C (CH3) 3 J-propyl, 2- (S02-CH3 Jbutyl, 2- (S02-C2H5) butyl, 2- (S02-CH2-C2H5) butyl, 2- [S0 -CH (CH3) 2 Jbutyl, 2- (S02-CH2CH2-C2H5) butyl, 2- (1-methylpropylsulfonyl) butyl, 2- (2-methylpropylsulfonyl) butyl, 2- [S02-C ( CH3) 3-Butyl, 3- (S02-CH3 Jbutyl, 3- (S02-C2H5 Jbutyl, 3- (S ?2-CH2-C2H5) butyl, 3- [S02-CH (CH3) 2] butyl, 3- (S02-CH2CH2-C2H5) butyl, 3- (1-methylpropylsulfonyl) butyl, 3- (2-Methylpropylsulfonyl) butyl, 3- [S02-C (CH) 3 Jbutyl, 4- (S02-CH3 Jbutyl, 4- (S02-C2H5) butyl, 4- (S? 2-CH2-C2H5) butyl, 4- [S02-CH (CH3) 21butyl, 4- (S02-CH2CH2-C2H5) butyl, 4- (1-methylpropylsulfonylbutyl, 4- (2-methylpropylsulfonyl) butyl or 4- [S02-C (CH3) 3 Jbutyl , especially CH2CH2S02-CH3 or CH2CH2S02-C2H5; C? -C4-halogenoalkylsulfonyl-C? -C4-alkyl: C? -C4-alkyl substituted by C? -C4-halogenoalkylsulfonyl as mentioned above, ie, p. 2- (2, 2, 2-trifluoroethylsulphonyl-ethyl; C? -C4-alkylamino-C? -C4-alkyl: C? -C4-alkyl substituted by C? -C4-alkylamino, such as, for example, H3C-NH-, H5C-H-, n-propyl-NH- , 1-methylethyl-NH-, n-butyl-NH-, 1-methylpropyl-NH-, 2-methylpropyl-NH- and 1,1-dimethylethyl-NH-, preferably H3C-NH- or H5C2-NH-, a know, for example, CH2CH2-NH-CH3, CH2CH2-N (CH3) 2, CH2CH2-NH-C2H5 or CH2CH2- (C2H5) 2; - (C -C4-alkylamino) carbonyl: C0-NH-CH3, C0-NH-C2H5, n-propylamino, C0-NH-CH (CH3) 2, C0-NH-CH2CH2-C2H5, C0-NH- CH (CH3) -C2H5, C0-NH-CH2-CH (CH3) 2 or C0-NH-C (CH3) 3, preferably C0-NH-CH3 or C0-NH-C2H5; - (C? -C6-alkylamino) carbonyl: one of the abovementioned (C? -C4-alkylamino) carbonyl radicals, or for example CO-NH- (n-C5H ??), l-methylbutyl- NHCO-, 2-methylbutyl-NHCO-, 3-methylbutyl-NHCO-, 2,2-dimethylpropyl-NHCO-, 1-ethylpropyl-NHCO-, CO-NH- (n-C6H13), 1,1-dimethylpropyl-NHCO -, 1, 2-dimethylpropyl-NHCO-, 1-methyl pentyl-NHCO-, 2-methylpentyl-NHCO-, 3-methylpentyl-NHCO-, 4-methyl-pentyl-NHCO-, 1,1-dime-ilbutyl- NHCO-, 1,2-dimethylbutyl-NHCO-, 1,3-dimethylbutyl-NHCO-, 2,2-dimethylbutyl-NHCC-, 2,3-dimethylbutyl-NHCO-, 3,3-dimethylbutyl-NHCO-, 1-ethylbutyl-NHCO-, 2-ethylbutyl-NHCO-, 1,1,2-trimethylpropyl-NHCO-, 1, 2, 2-trimethylpropyl-NHCO-, 1-ethyl-1-methylpropyl-NHCO- or -ethyl-2-methylpropyl-NHCO-, preferably C0-NH-CH3, CO-NH-C2H5, CO-NH-CH2-C2H5, CO-NH- - n- 6? 3; - (C? -C4-alkylamino) carbonyl-C? -C4-alkyl: (C? -C4-alkylamino) carbonyl as those mentioned above, preferably CO-NH-CH3 or CO-NH-C2H5, substituents C? -C4-alkyl, eg CH2-CO-NH-CH3, CH2-CO-NH-C2H5, CH2-CO-NH-CH2-C2H5, CH2-CO-NH-CH (CH3) 2, CH2-CO -NH-CH2CH2-C2H5, CH2-CO-NH-CH (CH3) -C2H5, CH2-CO-NH-CH2-CH (CH3) 2, CH2-CO-NH-C (CH3) 3, CH (CH3) -CO-NH-CH3, CH (CH3) -CO-NH-C2H5, 2- (CO-NH-CH3) ethyl, 2- (CO-NH-C2H5) ethyl, 2- (CO-NH-CH2-C2H5 ) - ethyl, 2- [CH2-CO-NH-CH (CH3) 2] ethyl, 2- (CO-NH-CH2CH2-C2H5) ethyl, 2- [CO-NH-CH (CH3) -C2H5-Jetyl, 2 - [CO-NH-CH2-CH (CH3) 2 Jetyl, 2- [CO-NH-C (CH3) 3 Jetyl, 2- (CO-NH-CH3) propyl, 2- (CO-NH-C2H5) pro - pyl, 2- (CO-NH-CH2-C2H5) J-propyl, 2- [CH2-CO-NH-CH (CH3) 2 J-propyl, 2- (CO-NH-CH2CH2-C2H5) propyl, 2- [CO-NH-CH (CH 3) -C 2 H 5] propyl, 2- [CO-NH-CH 2 -CH (CH 3) 2 J-propyl, 2- [CO-NH-C (CH 3) 3 J-propyl, 3- (CO -NH-CH3 Jpropyl, 3- (CO-NH-C2H5) propyl, 3- (CO-NH-CH2-C2H5) propyl, 3- [CH2-C0-NH-CH (CH3) 2] propyl ?, 3- (C0-NH-CH2CH2-C2H5) propyl, 3- [CO-NH-CH (CH3) -C2H5Jpropyl, 3- [CO-NH-CH2-CH (CH3) 2 J-propyl, 3- [CO-NH-C ( CH3) 3 J-propyl, 2- (C0-NH-CH3 Jbutyl, 2- (C0-NH-C2H5) -butyl, 2- (CO-NH-CH2-C2H5) butyl, 2- [CH2-C0-NH-CH (CH3) 2] butyl, 2- (CO-NH-CH2CH2-C2H5) butyl, 2- [CO-NH-CH (CH3) -C2H5] butyl, 2- [CO-NH-CH2-CH (CH3) 2 Jbutyl, 2- [CO-NH-C (CH3) 3 Jbutyl, 3- (CO-NH-CH3) butyl, 3- (CO-NH-C H5 Jbutyl, 3- (CO-NH-CH2-C2H5) - butyl, 3- [CH2-CO-NH-CH (CH3) 2 Jbutyl, 3- (CO-NH-CH2CH2-C2H5) butyl, 3- [CO-NH-CH (CH3) -C2H5 Jbutyl, 3- [CO-NH -CH2-CH (CH3) 2 Jbutyl, 3- [CO-NH-C (CH3) 3 Jbutyl, 4- (CO-NH-CH3 Jbutyl, 4- (CO-NH-C2H5) butyl, 4- (CO-NH-CH2-C2H5 Jbutyl, 4 - [CH -CO-NH-CH (CH3) 2 Jbutyl, 4- (CO-NH-CH2CH2-C2H5) butyl, 4- [CO-NH-CH (CH3) -C2H5 Jbutyl, 4- [CO-NH-CH2-CH (CH3) 2 Jbutyl or 4- [CO-NH -C (CH3) 3 -butyl, preferably CH2-C0-NH-CH3, CH2-C0-NH-C2H5 CH (CH3) -C0-NH-CH3. or CH (CH3) -CO-NH-C2H5. - di (C? -C4-alkyl) amino: N (CH3) 2, N (C2H5) 2, N, N-dipropylamino, N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N , N-di- (l-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N, N-di- (1,1-dimethylethyl) amino, N-ethyl-N-methylamino, N- methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2 -methylpropyl) amino, N- (1,1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl- N- (1-methylethyl) amino, N-butyl-N-ethylamino, N- ethyl-N- (1-methyl-propyl) amino, N-ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1,1-dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N- propylamino, N- (1,1-dimethylethyl) -N -propylamino, N-butyl- - -me and - - -, -, - tyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- ( 2-methylpropyl) amino, N-butyl-N- (1,1-dimethylethyl) -amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethyl) tl) -N- (1-methylpropyl) amino or N- (1,1-dimethylethyl) -N- (2-methylpropyl) amino, preferably N (CH 3) 2 or N (C 2 H 5) 2; di (C? -C4-alkyl) amino-C? -C4-alkyl: C? -C4-alkyl substituted by di (C? -C4-alkyl) -amino as mentioned above, namely, eg CH2N (CH 3) 2, CH 2 N (C 2 H 5) 2, N, N-dipropylaminomethyl, N, N-di [CH (CH 3) 2 J aminomethyl, N, N-dibutylaminomethyl, N, N-di- (1-methylpropyl) aminomethyl, N, -di (2-methylpropyl) aminomethyl, N, N-di [C (CH3) 3 Jaminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl-N- [CH (CH3 ) 2 Jaminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropylJaminomethyl, N-methyl-N- (2-methylpropyl) aminomethyl, N- [C (CH3) J-N-methylaminomethyl, N -ethyl-N-propylaminomethyl, N-ethyl-N- [CH (CH3) 2 Jaminome-tyl, N-butyl-N-ethylaminomethyl, N-ethyl-N- (1-methylpropyl Jaminomethyl, N-ethyl-N- ( 2-methylpropyl) aminomethyl, N-ethyl-N- [C (CH 3) 3 Jaminomethyl, N- [CH (CH 3) 2 JN-propylaminomethyl, N-buyl-N-propylaminomethyl, N- (1-methylpropyl) - N-propylaminomethyl, N- (2-methylpropyl) -N-propylaminomethyl, N- [C (CH3) 3] -N-propylammiomethyl, N-butyl-N- (1-methylethyl) -aminome linden, N- [CH (CH3) 21-N- (1-methylpropyl) aminomethyl, N- [CH (CH3) 2] -N- (2-methylpropylJaminomethyl, N- [C (CH3) 3] -N- [ CH (CH 3) 2 Jaminomethyl, N-butyl-N- (1-methylpropyl) aminomethyl, N-butyl-N- (2-methylpropyl) aminomethyl, N-butyl-N- [C (CH 3) 3 J -aminomethyl, N - (1-methyl-propyl) -N- (2-methylpropyl) aminomethyl, N- [C (CH 3) 3] -N- (1-methylpropyl) aminomethyl, N- [C (CH 3) 3 J -N- ( 2-methylpropyl) aminomethyl, N, N-dimethylaminoethyl, N, N-diethylaminoethyl, N, N-di (n-pro-p-phenylamino, N, N-di- [CH (CH 3) 2] -aminoethyl, N, N- dibutylami-noethyl, N, -di (1-methylpropylCheminoethyl, N, N-di (2-methylpropapyaminoethyl, N, N-di- [C (CH3) 3 J-aminoethyl, N-ethyl-N-methylamino- noethyl, N-methyl-N-propylaminoethyl, N-methyl-N- [CH (CH3) 2 Jaminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N- (1-methylpro-pyl) aminoethyl, N-methyl -N- (2-methylpropyl) aminoethyl, - [C (CH3) 3 JN-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-N- [CH (CH3) 2 Jaminoethyl, N-butyl-N-ethylaminoethyl , N-ethyl-N- (1-methylpropyl) aminoethyl, N-et il-N- (2-methylpropyl) aminoethyl, N-ethyl-N- [C (CH 3) 3 J aminoethyl, N- [CH (CH 3) 2 J-N-propylamino-tyl, N-butyl-N-propylaminoethyl, N- (1-methylpropyl) -N-propylaminoethyl, N- (2-methylpropyl) -N-propylaminoethyl, N- [C (CH 3) 3 JN-propylaminoethyl, N-butyl-N- [CH (CH 3) 2 Jaminoethyl, N- [CH (CH3) 2] -N- (1-methylpropyl) aminoethyl, N- [CH (CH3) 2] -N- (2-methylpropyl) -aminoethyl, N- [C (CH3) 3J- N- [CH (CH3) 2 Jaminoethyl, N-bu- neo, - - - 3 3, - -me - - (2-methylpropyl) aminoethyl, N- [C (CH3) 3 J -N- (1-methylpropyl ) - aminoethyl or N- [C (CH3) 3 JN- (2-methylpropylChaminoethyl, especially fN, N-dimethylaminoethyl or N, N-diethylaminoethyl; - di (C -C4-alkyl) aminocarbonyl: CO-N (CH3) 2, CO-N (C2H5), CO-N (CH2-C H5) 2, CO-N [CH (CH3) 2J2, N, N -dibutylaminocarbonyl, CO-N [CH (CH3) -C2H5] 2, CO-N [CH2-CH (CH3) 2J2, C0-N [C (CH3) 3J2, N-ethyl-N-methylaminocarbonyl, N-methyl-N -propylaminocarbonyl, N-methyl-N- [CH (CH3) 2] aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2- methylpropyl) aminocarbonyl, N- [C (CH 3) 3] -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- [CH (CH 3) 2 J -aminocarbonyl, N-butyl-N- ethylaminocarbonyl, N-ethyl-N- (1-methylpropap) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- [C (CH 3) 3 J aminocarbonyl, N- [CH ( CH3) 2 J-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- [C (CH3) 3 J-N-propylaminocarbonyl, N-butyl-N- [CH (CH 3) 2 J aminocarbonyl, N- [CH (CH 3) 2] -N- (1-methylpropyl) aminocarbonyl, N- [CH (CH 3) 2] -N- (2-methylpropyl) aminocarbonyl, N- [C (CH3) 3 J -N- [CH (CH3) 2J aminocarbonyl, N-butyl- N- (1-methylpropyl) aminocarbonyl , N-butyl-N- (2-methylpropyl) -aminocarbonyl, N-butyl-N- [C (CH3) J aminocarbonyl, N- (l-methyl-propyl) -N- (2-methylpropyl) aminocarbonyl, N- [C (CH3) 3 J-N- (1-methylpropyl) ammonocarbonyl or N- [C (CH3) 3] -N- (2-methylpropyl) aminocarbonyl, preferably CO-N (CH3) 2 or CO-N (C2H5 ); - di (C? -C6-alkyl) aminocarbonyl: one of the di (C? -C4-alkyl) aminocarbonyl radicals mentioned above, or for example N (CH3) - (n-C5H ??), N (C2H5) ) - (n-C5H ??), N (CH2-C2H5) - (n-C5H ??), N (n-C4H9) - (n-C5H ??), N (n-C5Hu) - (n- C5H ??), N (n-C6H? 3) - | n-C5Hn), N (CH3) - (n-C6H? 3), N (C2H5) - (n-C6H? 3), N (CH2-) C2H5) - (n-C6H? 3), N (n-C4H9) - (n-C6H13), N (n-C5H ??) - (n-C6H? 3) or N (n-C6H13) 2; di (C-C4-alkyl) aminocarbonyl-C? -C4-alkyl: C? -C4-alkyl substituted by di (C? -C4-alkyl) aminocarbonyl as mentioned above, preferably CO-N (CH3) 2 or CO -N (C2H5), namely, eg CH2-CO-N (CH3) 2, CH2-CO-N (C2H5) 2, CH (CH3) -C0-N (CH3) 2 or CH (CH3) -CO-N (C2H5) 2, preferably CH2-CO-N (CH3) 2 or CH (CH3) -CO-N (CH3J2; - di (C? -C4-alkyl) -phosphonyl-C? -C4-alkyl: C? -C-alkyl substituted by di (C? -C-alkyl) -phosphonyl, such as, for example -PO (OCH3) 2, -PO (OC2H5) 2, N, N-dipropylphosphonyl, N, N-di- (1-methylethyl) phosphonyl, N, N-dibutylphosphonyl, N, N-di- (1-methylpropyl) phosphonyl, nyl, N-ethyl -N-methylphosphonyl, N-methyl-N-propylphosphonyl, N-methyl-N-1-methylethyl) phosphonyl, N-butyl-N-methylphosphonyl, N-methyl-N- (1-methylpropyl) -phosphonyl, N-methyl- N- (2-methylpropyl) phosphonyl, N- (1, 1-dimethylethyl) -N-methylphosphonyl, N-ethyl-N-propyl-phosphonyl, N-ethyl-N- (1-methylethyl) phosphonyl, N- butyl-N-ethylphos-fonyl, N-ethyl-N- (1-methylpropyl) phosphonyl, N-ethyl-N- (2-methyl-propyl) phosphonyl, N-ethyl-N- (1,1-dimethylethyl) phosphonyl) , N- (1-methylethyl) -N-propylphosphonyl, N-butyl-N-propylphosphonyl, N- (1-methylpropyl) -N-propylphosphonyl, N- (2-methylpropyl) -N-propylphospho-nyl, N - (1, 1-dimethylethyl) -N-propylphosphonyl, N-butyl-N- (1-methylethyl) phosphonyl, N- (1-methylethyl) -N- (1-methylpropyl) phosphonyl, N- (1- methylethyl) -N- (2-methylpropyl) fo Sphonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) phosphonyl, N-butyl-N- (1-methylpropyl) phospho-nyl, N-butyl-N- (2-methylpropyl) phosphonyl, N -butyl-N- (1, 1-dimethylethyl) phosphonyl, N- (1-methylpropyl) -N- (2-methylpropyl) -phosphonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) phosphonyl) or N- (1,1-dimethylethyl) -N- (2-methylpropyl) phosphonyl, preferably -PO (OCH3) 2 or -PO (OC2H5) 2, namely, eg CH2-P0 (0CH3) 2, CH2-PO (OC2H5) 2, CH (CH3) -PO (OCH3) 2 or CH (CH3) -PO (OC2H5) 2; C -C6-alkenyl: prop-1-en-l-yl, allyl, 1-methyletenyl, 1-bu-ten-1-yl, l-buten-2-yl, l-buten-3-yl, 2- buten-1-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methyl- but-1-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl-but-l-en-l-yl, l-methyl-but-2-en-l- ilo, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en-l-yl, 2-methyl-but- 3-en-l-yl, 3-methyl-but-3-en-l-yl, 1, l-dimethyl-prop-2-en-l-yl, 1,2-dime-yl-prop-1- en-l-yl, 1,2-dimet-il-prop-2-en-1-yl, 1-ethyl-prop-l-en-2-yl, l-ethyl-prop-2-en-l-yl , n-hex-1-en-l-yl, n-hex-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-l-yl, n -hex-5-en-l-yl, 1-methyl-pent-l-en-l-yl, 2-methyl-pent-1-en-l-yl, 3-methyl-pent-l-en-l -yl, 4-methyl-pent-1-en-l-yl, l-methyl-pent-2-en-l-yl, 2-methyl-pent-2-en-l-yl, 3-methyl-pent -2-en-l-yl, 4-methyl-pent-2-en-l-yl, l-methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl 3-methyl-pent-3 -in-l-yl, 4-methyl-pent-3-en-l-yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3 -methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l-yl, 1, l-dimethyl-but-2-en-l-yl, 1,1-dimethyl-but -3-en-l-yl, 1, 2-dimethyl-but-l-en-l-yl, 1,2-dimethyl-but-2-en-l-yl, 1,2-dimethyl-but-3 -in-l-yl, 1,3-dimethyl-but-1-en-l-yl, l, 3-dimethyl-but-2-en-l-yl, 1,3-dimethyl-but-3-en -l-ilo, 2, 2-dimethyl-but-3-en-l-yl, 2,3-dimethyl-but-1-en-l-yl, 2,3-dimethyl-but-2-en-l -yl, 2, 3-dimethyl-ut-2-en-l-yl, 1-et l-but- -en- - o, -e-u - -en- - o, l-ethyl-but-3 -in-l-yl, 2-ethyl-but-l-en-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl-but-3-en-l-yl, 1 , 1,2-trimethyl-prop-2-en-l-yl, l-ethyl-l-methyl-prop-2-en-l-yl, l-ethyl-2-methyl-prop-1-en -l-ilo or l-ethyl-2-methyl-prop-2-en-l-yl; C3-Cg-halogenoalkenyl: C3-Cg-alkenyl as mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg 2-chloroalyl, 3-chloroalyl, 2,3-dichloroallyl, 3, 3-dichloroallyl, 2,3, 3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoalyl, 3-bromoalyl, 2,3-dibromoallyl, 3, 3- dibromoalyl, 2,3,3-tribromoalyl or 2,3-dibromo-but-2-enyl; cyano-C -C6-alkenyl: eg 2-cyanoalyl, 3-cyanoalyl, 4-cyanobut-2-enyl, 4-cyanobut-3-enyl or 5-cyanopent-4-enyl; - 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-l-in-4-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-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-yn-l-yl, n -hex-l-in-3-yl, n-hex-l-in-4-yl, n-hex-l-in-5-yl, n-hex-l-in-6-yl, n-hex -2-in-l-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3 -in-l-yl, n-hex-3-yn-2-yl, 3-methyl-pent-l-yn-l-yl, 3-methyl-pent-l-yn-3-yl, 3-methyl - pent-l-in-4-yl, 3-methyl-pent-l-in-5-yl, 4-methyl-pent-1-yn-l-yl, 4-methyl-pent-2-in-4 -yl and 4-methyl-pent-2-yn-5-yl, preferably prop-2-yn-l-yl; - C3-C6-haloalkylquinyl: C3-C6-alkynyl as mentioned above, which is partially or completely substituted by fluoro, chloro, bromo and / or iodo, namely, eg 1,1-difluoroprop-2 -in-l-yl, 4-fluorobut-2-yn-l-yl, 4-chlorobut-2-yn-l-yl, 1,1-difluorobut-2-yn-l-yl, 5-fluoropent-3 -in-l-yl or 6-fluoro-hex-4-yn-l-yl; - cyano-C3-C6-alkynyl: eg 3-cyanopropargyl, 4-cyanobut-2-yn-l-yl, 5-cyanopent-3-yn-l-yl and 6-cyanohex-4-yl -ilo; - C3-C4-alkenyloxy-C? -C4-alkyl: C-C4-alkyl substituted by C3-C4-alkenyloxy, such as, for example, allyloxy, but-l-en-3-yloxy, but-l-en- 4-yloxy, but-2-en-l-yloxy, l-methylprop-2-enyloxy or 2-methylprop-2-enyloxy substituents, viz., For example, pertain to 2-allyloxy ethers; C3-C4-alkynyloxy-C? -C -alkyl: C? -C -alkyl substituted by c3_c4-alkynyloxy, such as, for example, propargyloxy, but-l-in-3-yloxy, but-l-in-4- iloxy, but-2-in-l-yloxy, l-methylprop-2-ynyloxy or 2-methylprop-2-ynyloxy, preferably propargyloxy, viz., for example, propargyloxymethyl or 2-propargyloxyethyl, especially 2-propargyloxyethyl; C3-C4-alkenylthio-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C-alkenylthio, such as, for example, allylthio, but-l-en-3-ylthio, but-l-en- 4-ylthio, but-2-en-l-ylthio, l-methylprop-2-enylthio or 2-methylprop-2-enylthio, viz., For example, allylthiomethyl, 2-allylthioethyl or but-l-en-4- Ithiomethyl, especially für 2- (allylthio) ethyl; - < _3-C4-alkynylthio-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C4-alkynylthio, such as, for example, propargylthio, but-l-in-3-ylthio, but-l-in 4-ilthio, but-2-in-l-ilthio, l-methylprop-2-inylthio or 2-methylprop-2-inylthio, preferably propargylthio, viz., For example, propargylthiomethyl or 2-propargthylthioethyl, especially 2- (propargthylthio) -ethyl; - C3-C-alkenylsulfinyl-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C4-alkenylsulfinyl, such as, for example, allylsulfinyl, but-l-en-3-ylsulfinyl, but-l-en 4-ylsulfinyl, but-2-en-l-yl-sulfinyl, l-methylprop-2-enylsulfinyl or 2-methylprop-2-enylsulfinyl, viz., For example, allylsulfinylmethyl, 2-allylsulphylethyl or -l-en-4-ylsulfinylmethyl, especially für 2- (allylsulfinyl) ethyl; - C3-C4-alkynylsulfinyl-C? -C4-alkyl: C? -C -alkyl substituted by C3-C4-alkynylsulfinyl, such as, for example, propargyl-sulfinyl, but-l-in-3-ylsulfinyl, but-l-in 4-ylsulfinyl, but-2-yn-l-yl-sulfinyl, l-methylprop-2-ynylsulfinyl or 2-methylprop-2-ynylsulfinyl, preferably propargyl-sulfinyl, viz., For example, propargyl-sulfinylmethyl or 2-propargyl-sulfinylethyl, especially 2- (propargyl-sulfinyl) ethyl; C3-C4-alkenylsulfonyl-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C4-alkenylsulfonyl, such as, for example, allylsulfonyl, but-l-en-3-ylsulfonyl, but-l-en- 4-ylsulfonyl, but-2-en-l-yl-sulfonyl, l-methylprop-2-enylsulfonyl or 2-methylprop-2-enylsulphonyl, viz., For example, allylsulfonylmethyl, 2-allylsulfo-sulfonyl) ethyl; C3-C4-alkynylsulfonyl-C? -C4-alkyl: C? -C4-alkyl substituted by C3-C-alkynylsulfonyl, such as, for example, propargyl-sulfonyl, but-l-in-3-ylsulfonyl, but-l-in 4-ylsulfonyl, but-2-yn-l-yl-sulfonyl, l-methylprop-2-ynylsulfonyl or 2-methylprop-2-ynylsulphonyl, preferably propargyl-sulfonyl, viz., For example, propargylsulphonylmethyl or 2-propargyl-sulfonylethyl, especially , 2- (propargylsulfonyl) ethyl; - C3-Cg-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; - C3-C8-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; - C3-C8-cycloalkyl-C? -Cg-alkyl: eg cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, 2- (cyclopropyl) ethyl, 2- (cyclobutyljethyl, 2- (Cyclopentyl, Jetyl, 2- (cyclohexyl) ethyl, 2- (cycloheptyl, Jetyl, 2- (cyclooctyl) ethyl, 3- (cyclopropyl, Jpropyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl-propyl, 3- (cycloheptyl) propyl, 3- (cyclooctyl) propyl, 4- (cyclopropyl-Jbutyl, 4- (cyclobutyl) butyl, 4- (cyclopentyl-Jbutyl, 4- (cyclohexyl) -butyl, 4- ( cycloheptylbutyl, 4- (cycloocrylbutyl, 5- (cyclopropyl) pentyl, 5- (cyclobutyl) pentyl, 5- (cyclopentyl) -pentyl, 5- (cyclohexyl) pentyl, 5- (cycloheptyl) pentyl, 5- ( cyclooctyl) pentyl, 6- (cyclopropyl) hexyl, 6- (cyclobutyl) hexyl, 6- (cyclopentyl) hexyl, 6- (cyclohexyl) hexyl, 6- (cycloheptyl) hexyl or 6- (cyclooctyl) hexyl; - C3-C8-cycloalkyloxy-C? -C4-alkyl: cyclopropyloxymethyl, 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclopropyloxy-prop-1-yl, 2-cyclopropyloxy-prop-1-yl, 3-cyclopropyloxy-prop-1-yl, 1-cyclopropyloxy-but-1-yl, 2-cyclopropyloxy-butyl-1-yl, 3-cyclopropyloxy-but-1-yl, 4-cyclopropyloxy-butyl-1-yl, l-cyclopropyloxy-but-2-yl, 2-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 3-cyclopropyloxy-but-2-yl, 4-cyclopropyloxy-but-2-yl, 1- (cyclopropyloxymethyl) -et-1-yl, 1- (cyclopropyloxymethyl) -l- (CH 3) -et-1-yl, 1- (cyclopropylmethyloxy) -prop-1-yl, cyclobutyloxymethyl, 1- cyclobutyloxy-ethyl, 2-cyclobutyloxy-ethyl, 1-cyclobutyloxy-prop-1-yl, 2-cyclobutyloxy-prop-1-yl, 3-cyclobutyloxy-1-yl, 1-cyclobutyloxy-but-l- ilo, 2-cyclobutyloxy-but-1-yl, 3-cyclobutyloxy-but-1-yl, 4-cyclobutyloxy-but-1-yl, 1-cyclobutyloxy-but-2-yl, 2-cyclobutyloxy-1-yl , 4-c-clobut-ox-ut- - or, -ccou oxethyl) et-l-yl, 1- (cyclobutyloxymethyl) -l- (CH 3) -et-1-yl, 1- (cyclob) utiloxymethyl) prop-l-yl, cyclopentyloxymethyl, 1-cyclopentyloxy-ethyl, 2-cyclopentyloxy-ethyl, 1-cyclopentyloxy-prop-1-yl, 2-cyclopentyloxy-propyl-1-yl, 3-cyclopentyloxy-propyl 1-yl, 1-cyclopentyloxy-but-1-yl, 2-cyclopentyloxy-but-1-yl, 3-cyclopentyloxy-but-1-yl, 4-cyclopentyloxy-butyl-1-yl, l-cyclopentyloxy-butyl 2-yl, 2-cyclopentyloxy-but-2-yl, 3-cyclopentyloxy-but-2-yl, 3-cyclopentyloxy-but-2-yl, 4-cyclopentyloxy-but-2-yl, l- (cyclopentyloxymethyl) ) et-l-yl, l- (cyclopentyloxymethyl) -l- (CH3J- et-l-yl, l- (cyclopentyloxymethyl) prop-l-yl, cyclohexyloxymethyl, 1-cyclohexyloxy-ethyl, 2-cyclohexyloxy-ethyl , 1-cyclohexyloxy-prop-1-yl, 2-cyclohexyloxy-prop-1-yl, 3-cyclohexyloxy-1-yl, 1-cyclohexyloxy-but-1-yl, 2-cyclohexyloxy-but-1 -yl, 3-cyclohexyloxy-but-l-yl, 4-cyclohexyloxy-but-1-yl, l-cyclohexyloxy-but-2-yl, 2-cyclohexyloxy-but-2-yl, 3-cyclohexyloxy-but-2 -yl, 3-cyclohexyloxy-but-2-yl, 4-cyclohexyloxy-but-2-yl, l- (cyclohexyloxymethyl) et-1-yl, l- (cyclo) hexhexyloxymethyl) -l- (CH 3) -et-l-yl, 1- (cyclohexyloxymethyl) -prop-1-yl, cycloheptyloxymethyl, 1-cycloheptyloxy-ethyl, 2-cycloheptyloxy-ethyl, 1-cycloheptyloxy-prop -1-yl, 2-cycloheptyloxy-prop-1-yl, 3-cycloheptyloxy-1-yl, 1-cycloheptyloxy-but-1-yl, 2-cycloheptyloxy-but-1-yl, 3-cycloheptyloxy-but -l-ilo, 4-cycloheptyloxy-but-1-yl, l-cycloheptyloxy-but-2-yl, 2-cycloheptyloxy-but-2-yl, 3-cycloheptyloxy-but-2-yl, 3-cycloheptyloxy-but -2-yl, 4-cycloheptyloxy-but-2-yl, 1- (cycloheptyloxymethyl) et-1-yl, 1- (cycloheptyloxymethyl) -l- (CH 3) -et-1-yl, 1- (cycloheptyloxymethyl) prop-l-yl, cyclooctyloxymethyl, 1-cyclooctyloxy-ethyl, 2-cyclooctyloxy-ethyl, 1-cyclooctyloxyprop-1-yl, 2-cyclooctyloxy-propyl-l, 3-cyclooctyloxyprop-1-yl , 1-cyclooctyloxy-but-l-yl, 2-cyclooctyloxy-but-1-yl, 3-cyclooctyloxy-but-l-yl, 4-cyclooctyloxy-butyl-1-yl, l-cyclooctyloxy-but-2-yl , 2-cyclooctyloxy-but-2-yl, 3-cyclooctyloxy-but-2-yl, 3-cyclooctyloxy-but-2-yl, 4-cyclooctyloxy-but-2-yl or, 1- (cyclooctyloxymethyl) -et-1-yl, 1- (cyclooctyloxymethyl) -l- (CH 3) -et-1-yl or 1- (cyclooctyloxymethyl) prop-1-yl, especially C 3 -C6-cycloalkoxymethyl or 2- (C3-C6-cycloalkoxy) ethyl.
By "3- to 7-membered heterocycly" is meant both saturated, partially or completely unsaturated heterocycles, as well as aromatic heterocycles with one to three heteroatoms, selected from a group encompassing - one to three nitrogen atoms, - one or two sulfur atoms.
Examples of saturated heterocycles which may contain a mem-ber ring carbonyl or thiocarbonyl, are: oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-ils , oxetan-2-yl, oxetan-3-yl, tie-tan-2-yl, tietan-3-yl, acetidin-1-yl, acetidin-2-yl, aceti-din-3-yl, tetrahydrofuran-2 -yl, tetrahydrofuran-3-yl yl tetrahidrotiophen-2yl tetrahidrotiophen-3-yl pyrrolidin-1-yl-pyrrolidin-2,,,,, pyrrolidin-3-yl, l, 3-dioxolan-2 -yl, 1,3-dioxo-lane-4-yl, l, 3-oxathiolan-2-yl, l, 3-oxathiolan-4-yl, 1,3-oxathio-lane-5-yl, 1, 3 -oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazo-lidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1 , 2-oxa-zolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl , pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazole-1-yl, tetrahydropyrazole-3-yl, tetrahydropyrazole-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3 -yl, tetrahydropyran-4-yl, tetrahydrothio pi-ran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, pipe-ridin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, l, 3- dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dio-xan-2-yl, 1,3-oxatiane-2-yl, l, 3-oxatian-4-yl, 1,3-oxa-thian-5-yl, 1,3-oxatian-6-yl, 1,4-oxatian-2-yl, 1,4-oxa-tian-3- yl, morpholin-2-, morpholin-3-yl, morpholin-4-yl, hexahidropiridacin-1-yl, hexahidropiridacin-3-yl, hexahidrspirida-cin-4-yl-1-yl hexahydropyrimidin, hexahidropirimidin- 2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, pipera-cin-1-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-l, 3,5-triazin-l- ilo, hexahydro-l, 3,5-triazin-2-yl, oxe-pan-2-yl, oxepan-3-yl, oxepan-4-yl, tiepan-2-yl, tie-pan-3-yl, tiepan-4-yl, 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, l, 3- ditiepan-2-yl, l, 3-dithiepan-2-yl, l, 3-dithiepan-2-yl, l, 3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1, 4- dioxepan-7-yl, hexahydroazepin-1-yl, hexahydroazepin- 2-yl, hexahydroazepin-3-yl, hexahydroaze-4-yl, hexahydro-l, 3-diazepin-1-yl, hexahydro-1,3-diaze-2-yl, hexahydro-l, 3- diazepin-4-yl, hexahydro-l, 4-diaze-1-yl and hexahydro-1,4-diazepin-2-yl.
Examples of unsaturated heterocycles, which may contain an annular carbonyl or thiocarbonyl member, are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1, 3- oxazolin-2-yl; Among the heteroatoms, the five- and six-member members are preferred, ie, preferably, eg. nyl and 3-thienyl, pyrrolyl, such as, for example, 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as, for example, 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, eg 3 -isotiazolilo, 4-and 5-isotia- zolilo isotxazolilo, pyrazolyl, 3-pyrazolyl as eg 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-oxazolyl eg, 4-oxazolyl and 5-oxazolyl , thiazolyl, such as 2-thiazolyl eg, 4-thiazolyl and 5-thiazolyl, imidazolyl, 2-imidazolyl as eg 4-imidazolyl and, oxadiazolyl, eg 1,2, 4-oxadiazol 3-yl, l, 2,4-oxadiazol-5-yl and 1,3, -oxadiazol-2-yl, thiadiazolyl, such as, for example, 1,2,4-thiadiazol-3-yl, 1, 2, 4-thiadiazol-5-yl and 1,3,4-thia-diazol-2-yl, triazolyl, such as, for example, 1,2,4-triazol-1-yl, 1,4-triazole-3 -yl and 1, 2, 4-triazol-4-yl, pyridinyl, such as, for example, 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as, for example, 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl , such as, for example, 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, in addition, 2-pyrazinyl, 1, 3,5-triazin-2-yl and 1, 2,4-triazin-3-yl or, especially pyridyl, pyrimidyl, furanyl and thienyl.
All phenyl, carbocyclic and heterocyclic rings are preferably unsubstituted.
With respect to their use of the 3- (benzazol-4-yl) pyridinomenate I derivatives as herbicides, those compounds I are preferred, in which the variables have the following meanings, namely, by themselves or in combination: X oxygen; R1 hydrogen, airu.no or C? -C6-alkyl, especially hydrogen or C? -C4-alkyl, most preferably hydrogen or methyl; R2 hydrogen, halogen, C6C6alkyl, C6C6 haloalkyl or. C? -C6-alkylsulfsnyl, especially trifluoromethyl; R3 hydrogen; R4 hydrogen, fluoro or chloro; R5 cyano or halogen, especially chloro; = Y- R6 C? -C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -C6-alkylsulfonyl, (C? -C6-alkyl) carbonyl, (C? -C6-alkyl) thiocarbonyl, ( C6-C6-alkoxycarbonyl or C6-Cg-alkyl, which may be substituted by cyano, (C6-C6-alkoxy) carbonyl, di (C6-C6-ally C6-C6-alkyl, C3-C6-alkynyl, C? -C6-alkylsulfonyl or (C-C6-alkoxy) carbonyl.
The 3- (benzazol-4-yl) pyrimidinedione derivatives are most preferred. { = I with X = oxygen, R1 = methyl, R2 = trifluoromethyl, R3 = hydrogen, R4 = fluoro, R5 = chloro e = Y- = = C (ZR7) -N (CH3) -} especially, the following compounds Ia.l to 272; Table 1 In addition, the 3- (benza-zol-4-yl) pyrimidinedione derivatives of the formulas Ib to Ih, especially - the compounds Ib.l-Ib.272, which differ from the corresponding compounds Ia.l-la.272, only in that R4 means hydrogen: ZR7 the compounds Ic.l-lc.272, which differ from the corresponding compounds Ia.l-la.272 only in that R1 signifies hydrogen: ZR7 the compounds Id.l-Id.272, which differ from the corresponding compounds Ia.l-la.272 only in that R1 and R4 means hydrogen: the compounds Ie.l-le.272, which differ from the corresponding compounds Ia.l-la.272 only in that Y means = C (ZR7) -N (S02CH3) -: ZR7 compounds If.l - If.272, which differ from the corresponding compounds Ia.l-la.272 only in that R4 means hydrogen and Y means = C (ZR7) -N (S02CH3) -: ZR7 responding compounds Ia.l-la.272 only in that R1 means hydrogen and Y means = C (ZR7) -N (S0CH3) -: the compounds Ih.l-Ih.272, which differ from the corresponding compounds Ia.l-la.272 only in that R1 and R4 signifies hydrogen and Y signifies = C (ZR7) -N (S02CH3) -: ZR7 the compounds Ii.l-Ii.272, which differ from the corresponding compounds Ia.l-la.272 only in that = Y-means = C (ZR7) -0-: the compounds I.l-Ik.272, which differ from the corresponding compounds Ia.l-la.272 only in that = Y-means = C (ZR7) -0- and R4 means hydrogen: - the compounds Im.l-Im.272, which differ from the corresponding compounds Ia.l-la.272 only in that Y means = C (ZR7) -0- and R1 signifies hydrogen: the compounds In.l-In.272, which differ from the corresponding compounds Ia.l-la.272 only in that Y means = C (ZR7) -0- and R1 and R4 means hydrogen: The 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I can be obtained by different methods, for example, one of the following: Method A): Reaction of a 3- (benzazol-4-yl) pyrimidinedione derivative I, wherein R 1 signifies hydrogen, with a compound II in a manner known per se: L 1 denotes a customary cleavable group, such as, for example, halogen, preferably chlorine, bromine or iodine, (allogeneic) alkylsulfonyloxy, preferably methylsulfonyloxy or trifluoromethylsulfonyloxy, arylsulfonyloxy, preferably toluenesulfonyloxy, and alkoxysulfonyloxy, preferably methoxysulphonyloxy or ethoxysulfonyloxy.
It is usual to work in an inert organic solvent, for example in a protic solvent, such as, for example, lower alcohols, preferably in methanol or ethanol, if desired, in a mixture with water, or in an aprotic solvent, e.g. in an aliphatic or cyclic ether, such as, for example, methyl-tert-butyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aliphatic ketone, such as, for example, acetone, diethyl ketone and ethyl methyl ketone, in an amide , such as, for example, dimethylformamide and N-methylpyrrolidone, in a sulfoxide, such as, for example, dimethyl sulfoxide, in a urea, such as, for example, tetramethylurea and 1,3-dimethyltetrahydro-2 (lH) -pyrimidinone. , in a carboxylate, such as, for example, ethyl acetate, or in a halogenated aliphatic or aromatic hydrocarbon, such as, for example, dichloromethane, dichloroethane, chlorobenzene and the dichlorobenzenes.
If desired, it is possible to work in the presence of a base, with inorganic bases, for example carbonates, such as sodium carbonate and potassium carbonate, hydrogen carbonates, such as hydrogen carbonate, for example, being suitable. sodium and potassium hydrogencarbonate, or alkali metal hydrides, such as, for example, sodium hydride and potassium hydride, as well as organic bases, eg amine, s, as P-ex. triethylamine, pyridine and N, N-diethylaniline, or alcoholates of alkali metals, such as, for example, sodium methanolate, sodium ethanolate and tere. potassium butanolate.
In each case, the molar quantity is preferably, with respect to the quantity of the starting compounds I (with R1 = hydrogen).
Generally, the reaction temperature ranges from 0 ° C to the boiling temperature of the reaction mixture, especially from 0 to 60 ° C.
A preferred variant consists of alkylating the salt obtained from the IV cyclization according to Method D) with R1 = H or V with R1 = H, without isolation from the reaction mixture, which still contains excessive base, eg. Sodium hydride, sodium alcoholate or sodium carbonate.
In case the salts can not be prepared by the cyclization described as method D), the salts of those compounds I, in which R 1 signifies hydrogen, can also be obtained in a known manner from the process products of the Cj methods. to Fj. For this purpose, for example, the aqueous solution of an inorganic or organic base is mixed with the derivative of 3- (benzazol-4-yl) pyrimidinedione I, in which R 1 signifies hydrogen. The salt formation normally takes place at 20 to 25 ° C with sufficient velocity.
It is particularly favorable to prepare the sodium salt by dissolving the 3- (benzazol-4-yl) pyrimidinedione derivative I with R 1 = hydrogen in an aqueous solution of sodium hydroxide at 20 to 25 ° C, with approximately equimolar amounts of the derivative being used. of 3- (benzazol-4-yl) pyrimidinedione I (with R1 = H) and sodium hydroxide. The corresponding salt of the 3- (benzazol-4-yl) pyrimidinedione derivative I can then be isolated, eg, by precipitation with a suitable inert solvent or evaporation of the solvent.
The salts of the 3- (benzazol-4-yl) pyrimidinedione-a derivatives, whose metal ion is not an alkali metal ion, can be obtained, generally, by recrystallization of the corresponding alkali metal salts in aqueous solution; the same goes for the ammonium-, phosphonium, sulphonium and sulfoxonium salts through ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
Method B Reaction of a 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I, wherein R 1 signifies hydrogen, with an electrophilic amination reagent, in the presence of a base: As an amination reagent, 2,4-dinitrophenoxyamine has been especially proven, but it is also possible to use, for example, hydroxylamine-O-sulfonic acid (HOSA), which is already known from the literature as an amination reagent (see eg E. Hofer et al., Synthesis 1983, 466, W. Friedrichsen et al., Heterocycles 20 (1983) 1271, H. Hart et al., tetrahedron Lett 25 (1984) 2073, B. Vercek et al. al., Monatsh, Chem. 114 (1983) 789; G. Sosnousky et al., Z. Naturforsch. 738 (1983) 884; RS Atkinson et al., J. Chem. Soc. Perkin Trans. 1987, 2787).
The amination can be carried out in a manner known per se (see, for example, T. Sheradsky, Tetrahedron Lett, 1968, 1909, MP Wentland et al., J. Med. Chem. 27 (1984) 1103 and especially EP. -A 240 194, EP-A 476 697 and EP-A 517 181, where the amination of uracils is taught).
Normally, the reaction is carried out in a polar solvent, for example in dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide or in ethyl acetate, which has hitherto been shown to be particularly suitable.
Suitable bases are, for example, alkali metal carbonates, such as, for example, potassium carbonate, alkali metal alcoholates, such as, for example, sodium methylate and potassium tert-butolate, or alkali metal hydrides. , such as, for example, sodium hydride.
The amount of base and amination agent is preferably 0.5 to 2 times the molar amount, based on the starting compound.
Method C Sulfurization of a 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I, wherein X means oxygen: The sulfurization is generally carried out in an inert solvent or diluent, for example, in an aromatic hydrocarbon, such as, for example, toluene and the xylenes, in an ether, such as, for example, diethyl ether, 1,2-dimethoxyethane and tetrahydrofuran, or in an organic amine, such as, for example, pyridine.
Suitable sulfurization reagents are, in particular, phosphorus sulfide (V) and 2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane-2,4-dithione (reagent from "Lawesson") ).
Generally, it is sufficient to use the molar amount or 5 times the molar amount, with respect to the starting compound to be sulfided, to obtain a substantially complete transformation.
The reaction temperature normally varies from 20 to 200 ° C, preferably from 40 ° C up to the boiling temperature of the reaction mixture.
Cyclization of an arylurea of the formula III or an aryl of the formula IV in the presence of a base: I (X = O) L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
As a rule, it is cyclized in an inert organic solvent or diluent, which is aprotic, for example, in an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, in an aromatic, such as p. Examples of these are, for example, benzene and toluene or in a polar solvent, such as, for example, dimethylformamide and dimethyl sulfoxide. Mixtures of polar solvent and a hydrocarbon, such as, for example, n-hexane, may also be suitable. Depending on the starting compound, water can also be used as the solvent.
Suitable bases are, preferably, alkali metal alcoholates, especially sodium die alcoholates, alkali metal hydroxides, especially sodium hydroxide and potassium hydroxide, alkali metal carbonates, especially sodium carbonate and potassium carbonate, and metal hydrides, especially Sodium hydride When sodium hydride is used as a base, it has proven advantageous to work in an aliphatic or cyclic ether, in dimethylformamide or in dimethyl sulfoxide. e a ase, with respect to a can e e for the success of the reaction.
Generally, the reaction temperature varies from (-78) ° C to the boiling temperature of the corresponding reaction mixture, especially from (-60) to 60 ° C.
When R1 in formula III or IV means hydrogen, then a metal salt is obtained as a process product, the metal corresponding to the cation of the base used. The salt can be isolated and purified in a known manner, or transformed, if desired, by an acid in the free compound I with R1 = hydrogen.
Method E Treatment of a substituted 2-aminoaniline Va with nitrous acid Go I { = Y- = = N-N (R6) -} The cyclization reaction can be carried out by known methods (see, eg Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E8d, 1994 edition, pp. 409-415).
The reaction is preferably carried out in an acidic, aqueous medium, but also in lower carbonylic acids, such as P-ex. acetic acid, are suitable diluents. Suitable aqueous base solvents are especially dilute mineral acids, for example. example, 10% hydrochloric acid.
The nitrous acid is advantageously prepared in situ by adding an alkali metal nitrite - in the absence of solvent or as an aqueous solution - to the reaction mixture which is composed of diaminobenzene in aqueous solution, acid or in a carboxylic acid. specific to mind, 0 to, very specific to, approx. .
Conveniently, the educts are used in approximately stoichiometric amounts, or an excess of the theoretically expected amount in nitrous acid of 10 mol% is used, at most.
Analogously, the following intermediate product can be cyclized: VI VII Method F) Condensation of a substituted 2-aminophenol, 2-aminothiophenol or 2-aminoanilines (V) with carbonic acid or carboxylic acid derivatives: I (Z = chemical bond, O, NH, R7 = H, optionally alkyl, alkenyl or aryl) The condensation reaction of the bifunctional benzenes V with the carbonic acid or carboxylic acid derivatives is carried out in a manner known durchgeführt (see eg Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Vol. E8c, the 1994 edition, pp. 247-284; vol.E8b, the 1994 edition, pp. 881- 901; vol E8a, 1993 edition, pp. 1032-1078). Preferred carbonic acid or carboxylic acid derivatives are anhydrides, acid chlorides, orthoesters, diimides, nitriles, trichloromethyl substituted compounds, isocyanates or their yanates and their thio analogs. organic solvents, for example, aromatic hydrocarbons, such as, for example, benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform and dichloroethane, lower alcohols, such as ethanol, ethanol, aliphatic or cyclic ethers, such as, for example, dimethoxyethane, tetrahydrofuran and dioxane, carboxylate, such as, for example, ethyl acetate or polar aprotic solvents, such as, for example, dimethylformamide and dimethyl sulfoxide.
The reaction can be accelerated, if desired, by the addition of catalytic amounts of an acid. Suitable acids are, in particular, mineral acids, such as, for example, hydrochloric acids or sulfonic acids, such as, for example, p-toluenesulfonic acid. The amounts of acid are preferably 0.1 to 5 mol%, based on the amount of V.
The reaction temperatures preferably range from 20 ° C to the reflux temperature of the reaction mixture, especially from 60 ° C to the reflux temperature.
The carbonic acid or carboxylic acid derivative is used, or in amounts of approx. stoichiometric or in excess. In appropriate cases a larger excess can be used or it can be worked without solvent. Preferably, approximately stoichiometric amounts or an excess of up to 10 mol equivalents, with respect to the amount of V, will be used.
The 2-aminophenols, 2-thiophenoleans and substituted 2-anilines (V) are advantageously obtained by reduction of 2-nitrophenols, 2-thiophenols or 2-anilines corresponding to VIII (see, for example, Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Volume XI / 1, 4th edition 1957, pp. 431 f.): I am a e ementa e, as eg. erro, is a o and zinc, - hydrogen in the presence of suitable catalysts, such as eg palladium or platinum on carbon or Raney nickel, or complex hydrides, such as, for example, LiAlH4 and NaBH, optionally in the presence of catalysts.
Suitable solvents are generally, according to the reducing agent, carboxylic acids, such as, for example, acetic acid and propionic acid, alcohols, such as, for example, methanol and ethanol, ethers, such as, for example, diethyl ether. ether, methyl tert. -butyl ether, tetrahydrofuran and dioxane, aromatics, such as, for example, benzene and toluene, as well as mixtures of such solvents.
The reactions can be carried out at temperatures of (-100) ° C up to the boiling temperature of the corresponding reaction mixture.
Commonly, the starting compounds are used in amounts of approx. stoichiometric; in individual cases it may be advantageous to use an excess of the one or the other component of approx. 10% in mol.
The 2-nitrophenols, -thiophenols and -anilines VIII, on the other hand, can be liberated from the corresponding nitro-protected compounds IX: protection = usual protecting group protecting phenols or thiophenols as ethers or amino groups as amide. . . tive Groups in Organic Synthesis, John Wiley & Sons, Inc., 2a. 1991 edition, pgs. 145 and next and pages. 279 and next ).
Suitable separating reagents are, in particular: in the case of alkylphenols: trimethylsilyl iodide, boron tribromide, boron trichloride, aluminum trichloride, lithium chloride or hydrogen bromide; in the case of the benzylphenols or substituted benzylthiophenols: voro trifluoride hydrofluoric acid or hydrogen / catalyst, preferably a noble metal catalyst, such as, for example, palladium or platinum.
As the solvent / diluent, one must be chosen which is inert to the corresponding separation reagent. When the halides, trimethylsilyl iodide, voro tribromide, boron trichloride or aluminum trichloride are used, halogenated solvents, such as, for example, dichloromethane, chloroform, carbon tetrachloride and dichloroethane, are especially preferred. Hydrogen bromide is preferably used in aqueous solution, very preferably as a 48% solution; the lithium chloride is preferably used in polar solvents, such as, for example, lower alcohols, dimethyl sulfoxide and dimethylformamide; Hydrogenolytic methods are preferably used in lower alcohols or carboxylic acids, optionally with the addition of a hydrogen transducer, such as, for example, cyclohexene and cyclohexanediene.
The temperature for the separation reaction preferably varies from 0 ° C to the boiling temperature of the corresponding reaction mixture.
The separation reagent is preferably used in stoichiometric or excess amounts. The excess fluctuates, especially, between one and ten mol equivalents, with respect to the amount of IX.
Finally, the nitro-protected compounds IX can be prepared in a manner known per se by nitration of phenols, thiophenols or anilines (protected) x (see, for example, Houben-Weyl, Methoden der or-p gs., And s.
Suitable nitrating reagents are, in particular, nitric acid in a mixture with sulfuric acid or acetic anhydride, or nitronium salts, especially nitronium tetrafluoroborate. Composite mixtures of nitric acid and sulfuric acid may consist of arbitrary quantitative relationships of the two mixing components; those mixtures are preferred, in which the part of sulfuric acid strongly predominates or where it serves as a solvent. For the mixture of nitric acid and acetic anhydride, the same applies analogously. The nitronium tetrafluoroborate is preferably used in aprotic, polar solvents, for example in acetoneitrile or nitromethane.
The reaction temperature varies, generally, from (-80) to 80 ° C, especially from (-20) ° C to 30 ° C.
In nitrations with the nitric acid reagent it is preferred to work with an armoximously equimolar amount, or very preferably, with an excess of the nitrating reagent. The excess may amount to multiple times the amount of X. The nitronium tetrafluoroborate is preferably used in quantity with respect to the substrate or in a slight excess of between 1.1 and 1.5 mole equivalents.
Analogously, the following intermediate products can be nitrated: The 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I with one or more centers of chirality are generally obtained as enantiomeric or diastereomeric mixtures, which, if desired, are separated by conventional methods for this. end, eg by crystallization or chromatography on an optically active adsorbate, on the substantially pure isomers. The optically active isomers can be prepared, advantageously, from the corresponding optically active starting materials.
Those derivatives of 3- (benzazol-4-yl) pyrimidinedione of the formula I, in which R 1 signifies hydrogen, can be transformed in a manner known per se into their salts (cf. the explanations of the Method)).
The arylurof formula III are new. They can be obtained according to methods known per se, eg using the following method: Method G) Reaction of a β-ketocarboxylate XIII with a urea XIV: XIII XIV III L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
Preferably, working is carried out under essentially anhydrous conditions in an inert solvent or diluent, most preferably in the presence of an acid or basic catalyst.
As the solvent or diluent, organic solvents which are miscible with water with water in the form of azeotropes, for example aromatics, such as, for example, benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons, are particularly suitable. , such as, for example, methylene chloride, chloroform, tetraclo-rokohlenstoff and chlorobenzene, aliphatic and cyclic ethers, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or cyclohexane, but also alcohols, such as, for example, methanol and ethanol.
Suitable acid catalysts are preferably strong mineral acids, such as, for example, sulfuric acid and hydrochloric acid, phosphorus-containing acids, such as, for example, orthophosphoric and polyphosphoric acid, organic acids, such as, for example, p-toluenesulfonic acid, as well as acid cation exchangers, such as, for example, "Amber-lyst 15" (Cia. Fluka). e me a es a ca nos, as eg. r, especially, the alkali metal alcoholates, such as, for example, sodium methanolate and sodium ethanolate.
Conveniently, XIV and β-ketocarboxylate XIII are reacted in approximately stoichiometric amounts or a slight excess of one or the other component of ca. 10% in mol.
Normally, it is sufficient to use a catalyst amount of 0.5 to 2 mol%, with respect to the amount of one or the other of the starting compounds.
Generally, the reaction is carried out at a temperature of 60 to 120 ° C, to rapidly remove the water formed, preferably, it is carried out at the boiling temperature of the reaction mixture.
Method H) Reaction of an enol ether XV with a urea XVI: XV XVI III L2 and L3 each represent lower alkyl, preferably C, -C4-alkyl, or phenyl.
The reaction is preferably carried out in an inert organic solvent, miscible with water, for example an aliphatic or cyclic ether, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or a lower alcohol, especially ethanol, They have, preeren tly, aa empera ura eeuca meczla of reaction.
However, the reaction can also be carried out in an aromatic diluent, such as, for example, benzene, toluene and o-, m-, p-xylene, in which case it is advisable to add an acid catalyst, such as, for example, hydrochloric acid and p-toluenesulfonic acid, for example an alkali metal alcoholate, such as, for example, sodium methanolate and sodium ethanolate. Also in this variant, the reaction temperature rises, usually at 50 to 100 ° C, preferably at 60 to 80 ° C.
With respect to quantitative relationships, the indications for method G) are valid.
Method J Reaction of an enamino ester XVII with an isocyanate XVIII: XVII XVIII III L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
Conveniently, the reaction is carried out in the presence of an organic, aprotic, essentially anhydrous solvent or diluent, for example an aliphatic or cyclic ether, such as, for example, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, an aliphatic hydrocarbon. or aromatic, such as, for example, n-hexane, benzene, toluene and o-, m-, p-xylene, a halogenated aliphatic hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane and chlorobenzene, an aprotic, polar solvent, such as, for example, dimethylformamide, hexamethylphosphoric acid triamide and dimethyl sulfoxide, or a mixture of the solvents mentioned.
If desired, it is also possible to work in the presence of a metal hydride base, such as, for example, sodium hydride and potassium hydride or a tertiary organic base, such as.
Conveniently, the educts are reacted in stoichiometric quantities or a slight excess of one or the other component of ca. 10% in mol. When working without solvent in the presence of an organic base, this is present in a greater excess.
The reaction temperature varies, preferably from (-80) to 50 ° C, especially from (-60) to 30 ° C.
In an especially preferred variant, the ester III ester is converted to the excessive base directly (ie "in situ") according to method D) in the product of corresponding value I.
Method Kj Reaction of an enamin ester XVII with a urethane XIX: XVII XIX III L2 and L4 independently represent a low molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
This reaction is conveniently carried out in a polar aprotic solvent or diluent, such as, for example, dimethylformamide, 2-butanone, dimethyl sulfoxide and acetonitrile, and advantageously, in the presence of a base, for example, an alkali metal or alkaline earth metal alcoholate, in particular sodium alcoholate, such as, for example, sodium methanolate, a metal carbonate alkaline or alkaline earth metal, especially sodium carbonate, or an alkali metal hydride, such as, for example, lithium hydride and sodium hydride.
Normally, it is sufficient to use a quantity 1 to two times molar of the base, with respect to the amount of XVII or XIX. , pree in emen e ra tion of the reaction mixture.
With respect to the quantitative relationships of the starting compounds, the indications for method G) are valid.
In a particularly preferred variant, a sodium alcoholate is used as the base and the alcohol formed is continuously distilled in the course of the reaction. The thus obtained IV esters can be cyclized without isolation from the reaction mixture according to method D) in the salt of the substituted benzthiazole I (with R1 = H).
The urethanes XIX, for their part, can be prepared, for example, from carbon dioxide chloride XX and anilines XXI: XX XXI XIX To avoid an excess of aniline, generally, an auxiliary base, such as, for example, triethylamine, pyridine or the alkali metal carbonates has to be added to capture the hydrogen chloride formed in the reaction. Pyridine is found to be especially suitable, and can be used simultaneously as a solvent.
In addition to pyridine, aromatic hydrocarbons, such as, for example, benzene, toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform and dichloroethane, lower alcohols, such as, for example, methanol and ethanol, aliphatic or cyclic ethers, such as, for example, dimethoxyethane, tetrahydrofuran and dioxane, carboxylates, such as, for example, ethyl acetate, or aprotic solvents polar, such as, for example, dimethylformamide and dimethyl sulfoxide.
The reaction temperature generally ranges from 0 ° C to the reflux temperature of the corresponding reaction mixture. approx. This is not possible, or there is a carbonic excess of, at most, 10 percent in mol.
As an auxiliary base it is usually used, in an amount of approximately, equimolar - with respect to the quantity of XX or XXI - or in an exseco of approx. 2 times the molar amount. When pyridine is used as an auxiliary base, then it is advisable to use an even greater excess, in which case it is possible to work without additional solvent.
Method L) Reaction of an isocyanate XXII with an aniline derivative XXI: XXII XXI III (R1 = H) L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
This reaction is conveniently carried out in an organic, aprotic, substantially anhydrous solvent or diluent, for example in the presence of an aliphatic or cyclic ether, such as, for example, diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aliphatic or aromatic hydrocarbon, such as, for example, n-hexane, benzene, toluene or-, m-, p-xylene, a halogenated aliphatic hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride, 1,2- dichloroethane and chlorobenzene, an aprotic, polar solvent, such as, for example, dimethylformamide, hexamethylphosphoric acid triamide and dimethyl sulfoxide, or a mixture of the solvents mentioned.
If desired, it is also possible to work in the presence of a metal hydride base, such as, for example, sodium hydride and potassium hydride, an alkali metal or alkaline earth metal alcoholate, such as, for example, sodium methanolate, ethanolate of sodium and potassium tert-butanolate, or a nitrogenous organic base, such as, for example, triethylamine and pyridine, the organic base being used at the same time as a solvent.
This method allows you to use your computer in an excess of aprsx. 20% in mol. When working without solvent in the presence of an organic base, then this is advantageously present in an even greater excess.
The reaction temperature varies, generally, from (-80) to 150 ° C, preferably from (-30) ° C to the boiling temperature of the corresponding reaction mixture.
The arylanilides of the formula IV are also new; they can also be prepared in a manner known per se, for example, by reacting an amide XXIII with a urethane XXIV according to the method M): XXIII IV (R1 = H) L2 means lower molecular weight alkyl, preferably C? -C4 alkyl, or phenyl.
The reaction is advantageously carried out in a substantially anhydrous solvent / diluent at normal pressure, very preferably in the presence of an acid catalyst.
In order to obtain the IV enamincarboxylates with R1 = amino, it is advisable to react the compounds XXIV with the protected amino group (eg as hydrazone).
Suitable solvents / diluents are, in particular, organic liquids miscible with water in azeotropic form, for example aromatics, such as, for example, benzene, toluene and o-, m-, p-xylene or the halogenated hydrocarbons, such as .ej carbon tetrachloride and chlorobenzene.
Suitable catalysts are, in particular, strong mineral acids, such as, for example, sulfuric acid, organic acids, such as, for example, p-toluenesulfonic acid, phosphorus-containing acids, such as, for example, orthophosphoric acid and poly-acid. - pe. "Amberlyst 15" (Cia. Fluka).
Generally, a reaction temperature of approx. 70 at 150 ° C; but in order to be able to quickly remove the reaction water formed, the reaction is conveniently carried out at the boiling temperature of the corresponding reaction mixture.
XXIII and XXIV are generally used in amounts of approx. stoichiometric; but preferably a slight excess of XXIV of ca. 20% in mol.
The amide XXIII can be prepared, eg in the following manner (method N)): XXIII (R3 = H) XXV XXI The reaction is preferably carried out in an inert aprotic solvent, substantially anhydrous, for example in a halogenated hydrocarbon, such as, for example, methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, an aromatic hydrocarbon, such as, for example, benzene. , toluene and o-, m-, p-xylene, or an aliphatic or cyclic ether, such as, for example, diethyl ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane.
The reaction temperature varies, generally, from approx. 70 to 140 ° C, especially 100 to 120 ° C.
XXV and XXI are usually used in arpox quantities. stoichiometric, or the one or the other component is used in excess of approx. 10% in mol. er va os e an na seg n e m): XXI XVIII The method can be carried out in an inert diluent or diluent, substantially anhydrous or without solvent, the aniline derivatives XXI, preferably with phosgene, being converted into a "phosgene equivalent", such as, for example, diphosgene, triphosgene and carbonyldiimidazole or with chloroformate. trichloromethyl.
Examples of suitable solvents or diluents are organic solvents, aprotic solvents, for example dimethylformamide or aromatics, such as, for example, toluene and o-, m-, p-xylene, halogenated hydrocarbons, such as, for example, methylene chloride, chloroform, 1,2-dichloroethane and chlorobenzene, aliphatic or cyclic ethers, such as, for example, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, or esters, such as, for example, ethyl acetate, as well as mixtures of these solvents.
Conveniently, the educts are used in amounts of approx. stoichiometric, or the one or the other component is used in an excess of approx. 200% in mol.
According to the aniline derivative XXI formed, it may be advantageous to add a base, such as, for example, triethylamine, in an amount of 0.5 to 2 molar times, with respect to the quantity of XXI.
The reaction temperature generally ranges from (-20) ° C to the reflux temperature of the corresponding solvent or solvent mixture.
The aniline derivatives XXI in turn can be obtained in a manner known per se (see, for example, Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag Stuttgart, Volume XI / 1, 4th edition 1957, pp. 431 and sig.) by reduction of the corresponding XXVI nitrogenous derivatives: With regard to the reductant, solvent, reaction temperatures and quantitative ratios, refer to the indications for method F).
Compounds XXVIII and XXI may also contain one or more centers of chirality and are generally obtained as enantiomeric or diastereomeric mixtures. The mixtures can be separated, if desired, by methods customary for this purpose, eg by crystallization or chromatography on an optically active adsorbate, in the substantially pure isomers. The pure active isomers can also be obtained from the corresponding optically active starting materials.
Unless otherwise indicated, all the methods described above are used, suitably, under atmospheric pressure or under the proper pressure of the corresponding reaction mixture. Generally, the reaction components are used in a molar ratio of 0.95: 1 to 5: 1.
Further processing of the reaction mixtures can generally be carried out by methods known per se, for example by dilution of the reaction solution with water and subsequent isolation of the product by filtration, crystallization or extraction of the solvent, or by elimination of the solvent, distribution of the residue in a mixture from water and an appropriate organic solvent and further elaboration of the organic phase, giving the product.
The compounds I and their salts useful for agriculture are suitable, both in the form of isomeric mixtures, and also in the form of pure isomers, and as herbicides. Herbicidal products containing i are well suited to combat the growth of unwanted plants in areas not intended for cultivation, especially in high application quantities. In crops, such as wheat, rice, corn, soybeans and cotton, they are active against harmful grasses and gamines, without causing damage worthy of mention in the crop plants. This effect occurs mainly with low amounts of application.
They are compounds I or in the products that I use in additional plant crops to eliminate unwanted plants there. For example, the following crops are included: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, 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, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylestre, Ricinus communis, Saccharum officinarum, Sécale cereale , Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
In addition, compounds I can also be used in crops which have been made tolerant to the action of herbicides by culture or genetic engineering methods.
The compounds I or the products containing them can be used, for example, in the form of aqueous solutions, powders directly sprayable suspensions, also in the form of suspensions, dispersions or emulsions aqueous, oily or other highly concentrated, dispersions of oil , pastes, spraying agents, dusting agents or granules, by means of spraying, spraying, sprinkling or sprinkling. The forms of application depend on the purpose of the use; In any case, they must guarantee the finest possible distribution of the active substances of the invention.
Suitable as inert auxiliaries are mineral oil fractions ranging from medium to high boiling point, such as kerosene or diesel oil, in addition, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, such as paraffin, tetrahydronaphthaline. alkylated naphthalenes or their derivatives, alkylated benzenes, non-cyan or exanone, or energetic vehicles, N-methylpyrrolidone or water.
Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders or granules dispersible in water by the addition of water. To obtain emulsions, pastes or oil dispersions, the substrates can be homogenized as such or dissolved in an oil or solvent, by means of humectants, adherents, dispersants or emulsifiers, in water. However, a humectant, adherent, dispersant or emulsifier and, optionally, a solvent or an oil, can also be prepared from the active substance, which can be diluted with water.
Suitable surface-active substances are: alkali metal, alkaline earth metal, ammonium salts of aromatic sulphonic acids, eg lignin sulphonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalene sulfonic acid, as well as fatty acids, alkyl and alkylaryl sulfonates, sulfates of alkyether, lauryl ether and fatty alcohol, as well as salts of sulphonated hexa, hepta and octadecanols, as well as glycol ethers of fatty alcohol, sulfonated naphthalene condensates and their derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylenectyl-phenol ethers, isooctylphenol, octylphenol or nonylphenol ethoxylated, alkylphenol polyglycol ethers, tributylphenylpolyglycol ethers, alkylaryl polyether alcohols, isothri-decyl alcohol, condensates of fatty alcohol-ethylene oxide, castor oil ethoxylated, polyoxyethylene alkyl ethers, polyoxypropylene , acetal polyglycol ether lauryl alcohol, sorbitol esters, sulphite residual liquors and methylcellulose.
The spraying, spraying and atomizing agents can be obtained by mixing the active substances together with a solid support.
Granules, eg coated granules, impregnated granules and homogenous grains can be prepared by bonding the active substances with solid supports. Suitable solid supports are mineral earths, such as silica gel, silicic acids, silica gels, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastic, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as stone powders, bark powders of other solid supports.
The concentrations of active substances I in ready formulations can vary widely. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight of at least one active substance. The active substances are used in a purity of 90% bis 100%, preferably 95% up to 100% (according to NMR spectrum).
The following formulation examples illustrate the preparation of such preparations: I. 20 parts by weight of compound No. 1 are dissolved in a mixture containing 80 parts by weight of alkylated benzene, parts by weight of the addition product of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt ofdedecylbenzenesulfonic acid and 5 parts by weight of the product of adi - 40 moles of ethylene oxide to 1 mole of castor oil. By pouring 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 substance is obtained.
II. 20 parts by weight of compound No. 2 are dissolved in a mixture consisting 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 to 1 mole of isooctylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring 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 substance is obtained.
III. 20 parts by weight of the active substance No. 4 are dissolved in a mixture consisting of 25 parts by weight cyclohexanone, 65 parts by weight of a mineral oil fraction from the boiling point of 210 to 280 ° C and 10 parts by weight. by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring 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 substance is obtained. with 3 parts by weight of the sulfonated sodium sulphonates, 17 parts by weight of the sodium salt of a lignin sulphonic acid of a sulphite residual liquor and 60 parts by weight of pulverulent silica gel and milled in a hammer mill. By distributing the mixture finely in 20,000 parts by weight of water, a spray mixture containing 0.1% by weight of the active substance is obtained V. 3 parts by weight of the active substance No. 8 are mixed with 97 parts by weight of finely particulate kaolin. In this way, a spray agent containing 3% by weight of the active substance is obtained.
SAW. 20 parts by weight of the active substance No. 12 are intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol-polyglycol ether, 2 parts by weight of the sodium salt of a condensate of phenolsulfonic acid-urea-formaldehyde and 68 parts by weight of a paraffinic mineral oil. A stable oleic dispersion is obtained.
VII. 1 part by weight of compound 14 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of castor oil etc. Then, it can be diluted with water to the desired concentration. A stable emulsion concentrate is obtained.
VIII. 1 part by weight of compound 19 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone, 20 parts by weight of Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil, BASF AG). Then, it can be diluted with water to the desired concentration. A stable emulsion concentrate is obtained.
The compounds I or the herbicidal products that contain them can be applied before or after emergence. When the active substances are less tolerated by the crop plants, then application methods may be used in which the herbicidal products are sprayed with the aid of spraying apparatus in such a way that they do not fall on the leaves of the sensitive crop plants , but only on the leaves of the unwanted plants that grow below the primes - ee, ay- and.
The amounts of application in active substance I amount, depending on the respective application end, of the time of year, the target plants and their growth stage, to 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (sa).
In order to broaden the spectrum of action and to achieve synergistic effects, the compounds I can be mixed with numerous representatives of other groups of hervicidal active substances and growth regulators and applied in conjunction with these. Suitable mixing components are, for example, 1,2,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, (het) aryloxyalkanoic 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, quinolinecarboxylic acid and its derivatives, chloroacetanilides, derivatives of cyclohexane-1, 3-dione, diacins, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofu-ran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, di-pyridyls, halogenated carboxylic acids and their derivatives, ureas, phenyluracils, imidazoles, imidazolinones, N-phe nyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionates, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
In addition, it may be useful to apply the compounds I on their own or in combination with other herbicides also mixed with other phytosanitary products, for example products for combating phytopathogenic pests or fungi or bacteria. Also interesting is the miscibility with solutions of mineral salts, which are used to alleviate nutrient deficiencies or microelements. Non-phytotoxic oils and oil concentrates can also be used.
Example 1 3- [7-Chloro-5-fluoro-1-methyl-1H-benzotriazol-4-yl-1-methyl-6-trifluoromethyl-2- (4H, 3H) -pyrimidinedione (Compound 2) To a mixture of 0.25 g 3- [7-chloro-5-fluoro-1-methyl-1H-benzotria-zol-4-yl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione, 0, 12 g of potassium carbonate and 20 ml of absolute dimethylformamide are added in drops at 20 ° C 0.12 g of methyl iodide. Then, it is stirred for 18 hours, after which the reaction mixture is mixed with 50 ml of water. Then, 20 ml of ethyl acetate are extracted three times with each time. The combined organic phases are dried and finally concentrated. The crude product is purified by chromatography on silica gel (eluent: cyclohexane / ethyl acetate = 1: 1). Yield: 0.07 g; iH-NMR (270 MHz, CDC13): d [ppm] = 7.45 (d, lH), 6.45 (s, lH), 4.55 (s, 3H), 3.60 (s, 3H).
EXAMPLE 2 3- [7-Chloro-5-fluoro-l-methyl-lH-benzotriazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Comp.1) 0.13 g of sodium methylate in 7 ml of absolute dimethylformamide are mixed under a nitrogen atmosphere at 0 ° C within 15 minutes with 0.43 g of ethyl 3-amino-4,4,4-trifluorobut-2-enoate in 3 ml of dimethylformamide. It is stirred, first, for an hour and a half at 10 ° C, after which a solution of 0.57 g of 7-chloro-5-fluoro-l-methyl is added to the reaction mixture in drops within 15 minutes. ethyl -lH-benzotriazol-4-yl-carbamate in 20 ml of dimethylformamide. It is then heated to 20 ° C and stirred for 5 minutes. The mixture is then heated to 60 ° C and mixed with 0.35 g of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) Finally, it is stirred for 4 hours at 120 ° C and 18 hours at 20 ° C. For further processing, the mixture is poured into 100 ml of a 10% by weight aqueous solution of potassium, the valuable product is extracted with diethyl ether (twice 50 ml) and, after having regulated the Residual aqueous phase at a pH value of 1 is extracted with ethyl acetate (three times 30 ml) The combined organic phases are washed with approximately 20 ml of aqueous solution, saturated with sodium chloride and 30 ml of aqueous solution at room temperature. 10% by weight of lithium chloride, then dried over sodium sulfate and finally concentrated Yield: 0.25 g; H-NMR (250 MHz, in CDCl 3): d [ppm] = 10.25 (br, lH), 7.45 (d, lH), 6.30 (s, lH), 4.60 (s, 3H). -c gold- - uoro- - r uoroace To 100 g of 2-chloro-4-fluoroaniline in 800 ml of absolute diethyl ether are added in drops at 0 ° C 144.3 g of trifluoroacetic acid anhydride in 150 ml of diethyl ether. After heating to 20 ° C, the mixture is mixed with 500 ml of water. The organic phase is separated, washed three times with water, then dried over sodium sulfate and finally concentrated. Yield: 10 151.5 g; IFN-NMR (270 MHz, in CDC13): d [ppmj = 8.35 (br, lH), 8.25 (dd, lH), 7.20 (dd, lH), 7.05 (dt, lH).
Intermediate 2.2 15 3-chloro-5-fluoro-2-N-trifluoroacetylamino-nitrobenzene To 75 g of 2-chloro-4-fluoro-N-trifluoroacetylaniline in 753 ml of acetic anhydride, 375 ml of 98% nitric acid are slowly added dropwise at (-5) ° C. Then stir for one hour at (-5) ° C, then of which the mixture is heated to 20 ° C. The course of the reaction is followed by high pressure liquid chromatography on a column of RPi) -18 (eluent: acetonitrile / water = 7: 3). At the moment, when no educt can be checked, the reaction mixture is poured into a saturated, aqueous, ice-cold solution. sodium chloride. The solid product is then separated, washed with water and dried for several hours in the drying cabinet under reduced pressure at 20 ° C. Yield: 62.3 g; H-NMR (270 MHz, in CDC13): d [ppm] = 8.50 (br, lH), 7.80 (dd, lH), 7.60 (dd, lH).
Intermediate 2.3 3-chloro-5-fl-2- (N-methyl-N-triflacetylamino) -nitrobenzene To a mixture from 16.1 g of 3-chloro-5-fl-2-N-triflacetylamino-nitrobenzene, 11.6 g of potassium carbonate and 100 ml of absolute dimethylformamide are added 12.0 g of methyl iodide. It is then stirred for 18 hours at 20 ° C, after which the reaction mixture is mixed with 500 ml of water. It is then extracted three times with 100 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate and finally concentrated. Yield: 16.3 g; H-NMR (270 MHz, in CDCl 3): d [ppmj = 7.80 (m, 1 H), 7.60 (m, 1 H), 3.40 (s, 3 H). 5 - - To a solution of 16.3 g of 3-chloro-5-fl-2- (N-methyl-N-tri-flacetylamino) -nitrobenzene in 173 ml of ethanol is added 173 ml of an aqueous, 1-normal solution of sodium hydroxide. It is then stirred for 1 hour, after which the mixture is diluted with 500 ml of water. It is then extracted three times with 80 ml of ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and finally concentrated. Yield: 10.1 g; H-NMR (270 MHz, in CDC13): d [ppm] = 7.70 (dd, 1H), 7.35 (dd, 1H), 6.70-6.50 (br, 1H), 3.10 (d, 3H).
!) Reverse phase, on silica gel Intermediate 2.5 2-amino-6-chloro-4-fl-N-methylaniline To 10.1 g of 3-chloro-5-fl-2-methylamino-nitrobenzene in 207 ml of absolute ethanol is added 55.94 g of five dihydrate dichloride. The mixture is then heated to 50 ° C and 0.94 g of sodium borohydride in 55 ml of absolute ethanol are added in drops, so that the mixture does not come back stronger than 60 ° C. For further processing, pour over 1 liter of ice water, after which the mixture is adjusted with sodium hydroxide solution to a pH value of 14. It is then extracted three times with 100 ml of tert-butyl methyl ether. . The combined organic phases are washed with water, dried over sodium sulfate and finally concentrated. Yield: 7.5 g; H-NMR (270 MHz, in CDC13): d [ppm] = 6.50 (dd, lH), 6.35 (dd, lH), 3.90-3.60 (br, 3H), 2.65 (s, 3H).
Intermediate 2.6 7-chloro-5-fl-1-methylbenzotriazole To 7.5 g of 2-amino-6-chloro-4-fl-N-methylaniline in 117 ml of 10% hydrochloric acid is added at 5 ° C a solution of 3.25 g of sodium nitrite in 19 ml of Water. After stirring for one hour at 5 ° C, the reaction mixture is diluted with 200 ml of water. Then the solid proportion is separated, washed with 3x50 ml of water g and dried at 20 ° C in the vacuum drying cabinet. Yield: 7.2 g; iH-NMR (270 MHz, CDC13): d [ppmj = 7.60 (dd, 1H), 7.30 (dd, 1H), 4.55 (s, 3H).
- - - - - - - To 1.5 g of 7-chloro-5-fl-1-methylbenzotriazole in 28 ml of concentrated sulfuric acid, 0.65 ml of 98% nitric acid are slowly added dropwise at (-20) ° C. It is then stirred for one hour at 0 ° C, after which the mixture is heated to 20 ° C. The mixture is then stirred for 18 hours and the reaction mixture is then poured into 500 ml of ice water. The solid proportion is separated, washed with water and dried at 20 ° C in the vacuum drying cabinet. Yield: 1.66 g; iH-NMR (270 MHz, CDC13): d [ppmj = 7.50 (d, lH), 4.65 (s, 3H).
Intermediate 2.8 4-amino-7-chloro-5-fl-1-methylbenzotriazole 1.66 g of 7-chloro-5-fl-l-methyl-4-nitrobenzotriazole are reduced in analogy to intermediate 2.5 with tin dichloride / sodium boranate. Yield: 1.27 g; iH-NMR (250 MHz, en (CD3) 2SO): d [ppmj = 7.45 (d, lH), 6.25 (br., 2H), 4.45 (s, 3H), 4.30 (q, 2H), 1.35 (t , 3H).
Intermediate 2.9 ethyl 7-chloro-5-fl-1-methyl-lH-benzotriazol-4-yl-carbaminate To 13 ml of absolute pyridine, 2.28 g of ethyl chloroformate are slowly added dropwise at 0 ° C., after which it is stirred for 15 minutes at this temperature. Then, 1.27 g of 4-amino-7-chloro-5-fl-1-methylbenzotriazole in 20 ml pyridine are added dropwise at 0 ° C. Next, it is stirred, first, another 30 minutes at 0 ° C, then it is heated to 20 ° C and stirred again for 18 hours. Finally, the reaction mixture is poured into 100 ml of 10% hydrochloric acid. It is then extracted three times with 50 ml of tert-butyl methyl ether. The combined organic phases are washed with 100 ml of gewaschen water and then concentrated.
The residue is mixed with 50 ml of diethyl ether. The undissolved proportion is separated and washed with 3x30 ml of diethyl ether. The ethereal facies gathered are concentrated. Yield: 0.37 g; H-NMR (250 MHz, in CDC13): d [ppmj = 7.35 (d, lH), 6.90 (br., LH), 4.55 (S, 3H). - [-c oro- - uoro-l-met- -tr uorome- - enz m a-zol-4-yl] -l-methyl-6-trifluoromethyl-2,4 (1 H, 3 H) -pyrimidinedione (Comp. 1.5) 2.46 g of 3- [7-chloro-5-fluoro-l-methyl-2-trifluoromethyl-lH-benzi- midazol-4-yl] -6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione are rented in analogy to Example 1 with methyl iodide. Purification of the crude product is carried out by chromatography on sili-cagel (eluent: cyclohexane / ethyl acetate = 2: 1). Yield: 1.4 g; H-NMR (250 MHz, in CDC13): d [ppm] = 7.35 (d, lH), 6.40 (s, lH), 4.30 (S, 3H), 3.55 (s, 3H).
Example 4 3- [7-Chloro-5-fluoro-l-methyl-2-trifluoromethyl-lH-benzimide-zol-4-yl-1-amino-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione ( Comp 6) To a mixture from 0.5 g of 3- [7-chloro-5-fluoro-l-methyl-2-trifluoromethyl-lH-benzimidazol-4-yl-6-trifluoromethyl-2,4-trifluoromethyl] (lH, 3H) - pyrimidinedione, 2.35 g of potassium carbonate and 5 ml of ethyl acetate are added 0.25 g of 2,4-dinitro-O-aminophenol. After stirring for 18 hours at 20 ° C, it is diluted with 50 ml of ethyl acetate. The mixture obtained is washed with 3x30 ml of water, dried over sodium sulfate and finally concentrated. The crude product is purified by medium pressure liquid chromatography (MPLC, eluent: cyclohexane / ethyl acetate = 2: 1). Yield: 0.4 g; H-NMR (250 MHz, in CDC13): d [ppm] = 7.35 (d, lH), 6.30 (s, lH), 4.65 (s, 2H), 4.25 (s, 3H).
Example 5 3_ [7-Chloro-5-fluoro-1-methyl-2-trifluoromethyl-1H-benzimide-zol-4-yl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound 4) To 0.82 g of sodium hydride in 50 ml of absolute dimethylformamide are added dropwise at 0 to 5 ° C 4.31 g of ethyl 3-amino-4,4,4-trifluo-robut-2-enoate in 20 g. ml of dimethylformamide. It is then stirred for one hour at the same temperature, after which the mixture is mixed at (-30) ° C with 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-trifluoromethylbenzimidazole (from the product intermediate 5.4) in 40 ml of dimethylformamide. Then, one hour is stirred at (-30) ° C and another hour at 20 ° C.
I am afraid of water. After 10% hydrochloric acid a solid is obtained, which is filtered, washed with water and dried at 20 ° C in the vacuum drying cabinet. After purification by flash cormatofraphy (eluent: cyclohexane / ethyl acetate = 2: 1), 5.08 g of valuable product are obtained.
The valuable product that is still in the filtrate after having separated the solid proportion (2.46 g) is isolated by extracting three times with 200 ml of tere. -butyl methyl ether, washing the combined ether phases, drying over sodium sulfate and concentrating. Total yield: 7.54 g; H-NMR (250 MHz, in CDCl 3): d [ppm] = 7.40 (d, 1 H), 6.30 (S, 1 H), 4.30 (S, 3 H).
Intermediate 5.1 7-chloro-5-fluoro-l-methyl-2-trifluoromethylbenzimidazole .5 g of 3-chloro-5-fluoro-2- (-methyl-N-trifluoroacetylamino) -nitrobenzene (from intermediate 2.3) are reduced in analogy to intermediate 2.5 with tin dichloride / bora-nato sodium without intermediate isolation, giving the corresponding amino compound, which is then cyclized spontaneously under water separation in the product of value. Yield: 9.32 g; H-NMR (250 MHz, in CDCl 3): d [ppm] = 7.45 (d, 1 H), 7.20 (d, 1 H), 4.25 (s, 3 H).
Intermediate 5.2 7-Chloro-5-fluoro-1-methyl-4-nitro-2-trifluoromethylbenzimidazole To 9.65 g of 7-chloro-5-fluoro-l-methyl-2-trifluoromethylbenzimidazole in 96.5 ml of acetic anhydride, 46.3 ml of 98% nitric acid are slowly added at 0 ° C. After stirring for one hour at 0 ° C, the mixture is carefully heated to 20 ° C. (When an exothermic reaction is present, then the temperature is maintained by a water bath below 25 ° C.) Then, it is still stirred for two hours at 20 ° C and the reaction mixture is then poured into aqueous solution. , saturated with common salt. The proportion of solid formed is separated, washed with gewaschen water and dried at 20 ° C in the vacuum drying cabinet. Yield: 8.5 g; fí-NMR (400 MHz, in CDC13): d [ppmj = 7.40 (d, lH), 4.35 (s, 3H). - - - - - or - - - - 8.71 g of 7-chloro-5-fluoro-l-methyl-4-nitro-2-trifluoromethylbenzi-midazole are reduced in analogy to intermediate 2.5 by tin dichloride / sodium boranate. Yield: 6.3 g; ! H-MR (270 MHz, in CDC13): d [ppm] = 7.05 (d, lH), 4.45 (br, 2H), 4.20 (s, 3H).
Intermediate 5.4 7-chloro-5-fluoro-4-isocyanato-l-methyl-2-trifluoromethylbenzimidazole To 6.3 g of 4-amino-7-chloro-5-fluoro-l-methyl-2-trifluoromethylben-zimidazole in 100 ml of absolute toluene is added 23.32 g of diphosgene. Then, it is heated for 6 hours at reflux temperature. After stirring for a further 18 hours at 20 ° C, the reaction mixture is concentrated. The obtained crude product is transformed without further purification directly giving the final product 1.4.
Example 6 3- [7-Chloro-l, 2-dimethyl-5-fluoro-lH-benzimidazol-4-yl-1-methyl-6-trifluoromethyl-2,4 (1H, 3H) -pyrimidinedione (Compound 8 ) 0.33 g of 3- [7-chloro-l, 2-dimethyl-5-fluoro-lH-benzimidazol-4-ylJ-6-trifluoromethyl-2, (1H, 3H) -pyrimidinedione are alkylated in analogy to Example 1 with methyl iodide. Yield: 0.04 g; H-NMR (250 MHz, in CDC13): d [ppmj = 7.10 (d, lH), 6.40 (s, lH), 4.00 (s, 3H), 3.55 (s, 3H), 2.55 (s, 3H) .
Example 7 3- [7-Chloro-l, 2-dimethyl-5-fluoro-lH-benzimidazol-4-yl] -6-trifluo-romethyl-2,4 (1 H, 3 H) -pyrimidinedione (Compound 7) The 7-chloro-l, 2-dimethyl-5-fluoro-4-isocyanatobenzimidazole of intermediate 7.4 is reacted in analogy to example 5 with ethyl 3-amino-4,4,4-trifluorobut-2-enoate. The crude product is purified by medium pressure liquid chromatography (eluent: ethyl acetate / methanol = 15: 1). Yield: 0.7 g; H-NMR (270 MHz, in CDC13): d [ppmj = 7.15 (d, lH), 6.20 (s, lH), 4.05 (s, 3H), 2.55 (S, 3H). - -, - e - - To 6.96 g of 2-amino-6-chloro-4-fluoro-N-methylaniline (from intermediate 2.5) in 4.1 g of acetic anhydride is added 100 ml of 10% hydrochloric acid. Then, it is heated for 4 hours at reflux temperature. After cooling, the mixture is absorbed in ice water. It is then carefully neutralized with an aqueous solution of sodium carbonate. The solid crude product formed is separated, washed with gewaschen water and dried at 20 ° C in the vacuum drying cabinet. Yield: 7.92 g; XH-NMR (270 MHz, in CDC13): O [ppm] = 7.25 (dd, 1H), 6.95 (dd, 1H), 4.00 (s, 3H), 2.55 (s, 3H).
Intermediate 7.2 7-chloro-l, 2-dimethyl-5-fluoro-4-nitrobenzimidazole To 7.92 g of 7-chloro-l, 2-dimethyl-5-fluorobenzimidazole in 139 ml of concentrated sulfuric acid are added in goras to (-5) up to a maximum of 0 ° C 98% nitric acid, controlling the course of the reaction by high pressure liquid chromatography (HPLC) on a RP-18-Saule column (eluent: acetonitrile / water = 1: 1). At the time, when no eluent can be checked, the reaction mixture is poured into ice water, after which the pH value is regulated by sodium hydroxide solution to 14. The solid is separated, washed with water and at 20 ° C in the vacuum drying cabinet. The regioisomeric nitrogenous compounds formed are separated by flash silica gel chromatography (eluent: ethyl acetate, the product eluting first the desired regioisomer). Yield: 5.6 g; H-NMR (400 MHz, in CDCl 3): d [ppm] = 7.05 (d, 1 H), 4.10 (s, 3 H), 2.65 (s, 3 H).
Intermediate 7.3 4-amino-7-chloro-l, 2-dimethyl-5-fluorobenzimidazole .6 g of 7-chloro-l, 2-dimethyl-5-fluoro-4-nitrobenzimidazole are re-produced in analogy to intermediate 2.5 by tin dichloride / sodium boranate. The crude product obtained is directly transformed without further purification into intermediate 7.4. Yield: 4.1 g. - - , - me - - - - 4.1 g of 4-amino-7-chloro-l, 2-dimethyl-5-fluorobenzimidazole was reacted analogously to intermediate 5.4 with diphosgene. The raw product obtained was transformed directly, that is, without further purification, into the final product 1.7.
EXAMPLE 8 10 3- [7-Chloro-2-dimethylamino-5-fluorobenzoxazol-4-yl-1-methyl-6-trifluoromethyl-2, 4- (1 H, 3 H) -pyrimidinedione (Compound 19) 1.0 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione are mixed in 100 g. ml of 1,2-di-chloroethane with 0.5 g of dichloromethylene imonium chloride, after which the glass insert for pressure vessels is introduced and heated in the closed pressure vessel for 5 hours to 120 hours. ° C. The pressure of the pressure vessel itself increases to approx. 5 bar Next, the container is cooled. The clear product solution is washed with dilute aqueous potassium carbonate solution. The organic phase is dried over sodium sulfate and finally concentrated. The crude product is purified by flash chromatography, using a short column (eluent: cyclohexane / tert.-butadylmethyl ether = 8: 2). Yield: 0.5 g; H-NMR (270 MHz, in CDC13): d [ppm] = 6.85 (d, lH), 6.4 (s, lH), 3.6 (s, 3H), 3.25 (s, 6H).
Intermediate 8.1 30 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -l-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione To 51.0 g of 3- [4-chloro-6-fluoro-3-methoxyphenyl] -1-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione in 1: 1 sulfuric acid Concentrate in droplets under cooling at (-20) ° C, slowly, nitrating acid composed of 20.4 ml of concentrated sulfuric acid and 25.5 ml of 98% nitric acid. When the addition is complete, 30 minutes are stirred at (-20) ° C. The reaction mixture is then introduced under stirring in 1 liter of ice water. The proportion of solid formed is separated, washed with gewaschen water and dried in the vacuum drying cabinet at 20 ° C. Performance: , 57.0 g; H-NMR (270 MHz, in CDC13): d [ppm] = 7.55 (d, lH), 6.35 (S, 1H), 4.05 (s, 3H), 3.55 (s, 3H). 45 - - - - - - - - - - - - - methyl-2, 4- (1H, 3H) -pyrimidinedione to 57.0 g of 3- [4-chloro-6-fluoro-3-methoxy-2-nitrophenyl] -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in ca. 500 ml of absolute dimethylformamide is added 19.0 g of lithium chloride. Then, stir 3 hours at 80-90 ° C. After cooling, the reaction mixture is mixed with 1 l of water. The 10-value product is extracted with 3x200 ml methyl-tert-butyl ether. dThe ether phase is washed several times with water, then dried and finally concentrated. Yield: 46.1 g; iH-NMR (250 MHz, in CDC13): d [ppmj = 7.65 (d, lH), 6.35 (s, lH), 3.60 (s, 3H). 15 Intermediate 8.3 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione To 46.0 g of 3- [4-chloro-6-fluoro-3-hydroxy-2-nitrophenyl] -1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione in 423 ml of water and 36.8 ml of concentrated hydrochloric acid are added at 65 ° C in portions 34 g of iron powder. Then, it is heated for 3 hours at reflux temperature. After cooling, The mixture is stirred with 500 ml of ethyl acetate. Filtration on Celite (Manville Corporation) releases the organic phase of the inorganic material remains. The filtrate is dried over sodium sulfate and finally concentrated. Yield: 37.5 g; 30 H-NMR (270 MHz, in CDCl 3): d [ppm] = 6.65 (d, 1 H), 6.40 (s, 1 H), 3.60 (s, 3 H).
Example 9 3- [7-Chloro-5-fluorobenzoxazol-4-yl J-l-methyl-6-trifluoromethyl-2,4- (lH, 3 H) -pyrimidinedione (Comp.12) To a solution of 0.5 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2, 4- (1H, 3H) -pyrimidinedione (from intermediate product 8.3) in 30 ml of absolute methanol is added 40.5 g of trimethyl orthoformate. The solvent and the excessive orthoester are then removed under reduced pressure. The residue is dissolved in ethyl acetate. The organic phase is washed with water, then dried over sodium sulfate and finally concentrated. The crude product is purified by flash chromatography (eluent: cyclohexane / tert-butyl methyl ether = 3: 1). Yield: 0.26 g; fc3h. ,,. ,.
EXAMPLE 10 5- [7-Chloro-5-fluoro-2-methoxybenzoxazol-4-yl-1-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (Compound 14) 1.0 g of 3- [2-amino-4-chloro-6-fluoro-3-hydroxyphenyl] -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione (of the product in -10 termedium 8.3), analogue example 9 is reacted with tetramethyl orthoformate. Yield: 0.7 g; l-H-NMR (250 MHZ, in CDCl 3): d [ppm] = 7.10 (d, 1 H), 6.40 (S, 1 H), 4.20 (s, 3 H), 3.60 (s, 3 H).
In Table 2 below other 3- (benzazol-4-yl) pyrimidinedione derivatives of the formula I are indicated in addition to those described above, which were prepared or can be prepared analogously: twenty 40 45 Table 2 H; R5 = Cl.}. 00 Application examples The herbicidal action of the 3- (benzazol-4-yl) pyrimidinedione I derivatives can be demonstrated by the following greenhouse tests: Plastic pots filled with clay sand with approx. 3.0% humus as substrate. The seeds of the test plants are sown separately according to the species.
In the treatment before the emergency, actibas substances suspended or emulsified in water are applied directly after sowing by means of fine distribution nozzles. The containers are irrigated slightly to encourage germination and growth, and then the pots are covered with transparent plastic bags until the plants have taken root. With this covering a uniform germination of the test plants is reached, as this is not counteracted by the active substances.
For the post-emergence treatment, the test pan is grown until it has reached a growth height of 3 to 15, depending on its growth pattern, and then treated with the active substances suspended or emulsified in water. For this purpose, the test plants are sown directly in the same containers in which they are grown, or they are sown in separate germination containers and the seedlings are planted some days before the treatment in the test vessels. The amount of application in the treatments after the emergency amount to 15.6 or 7.8 g / ha of s.a.
The plants were maintained according to their species at temperatures of 10 to 25 ° C or 20 to 35 ° C. The trial period amounted to 2 to 4 weeks. During this time, the plants were taken care of and their reaction to the different treatments was evaluated.
The assessment is based on a scale of 0 to 100, where 100 means no emergence or total destruction of at least the parts of the plants surfaced, and 0 means no damage or normal growth.
The plants used in the trials in the greenhouse belong to the following species: Applied in quantities of 15.6 and 7.8 g / ha of s.a., compound No. 18 presents a very good herbicidal action in postemergence treatments against the weeds indicated above.

Claims (4)

  1. Derivatives of 3- (benzazol-4-yl) pyrimidinedione of the formula I in which the variables have the following meanings: X oxygen or sulfur; Ri hydrogen, amino, C? -C6-alkyl or C? -C6-halogenoalkyl; R 2 hydrogen, halogen, C 6 -C alkyl, C 6 -Chaloalkyl, C 6 -C alkylthio, C 6 -C alkylsulfinyl or C 6 -C 6 alkylsulphonyl; R3 hydrogen, halogen or C? -C6 alkyl; R4 hydrogen or halogen; R5 cyano, halogen, C? -C6-alkyl, C? -C6-haloalkyl, C? -C6-alkoxy or C? -C6-halogenoalkoxy; = Y- one group = N-N (R6) -, = C (ZR7) -N (R6) -, = C (ZR7) -0- or = C (ZR7) -S-; R6 C? -Cg-alkyl, C? -C4-haloalkyl, C3-Cg-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C? -Cg-alkylsulfonyl, (C? -Cg-alkyl) carbonyl, (C? -C6-haloalkyl) carbonyl, (C? -C6-alkyl) thiocarbonyl, (C? -C6-alkoxy) carbonyl, (C? -Cg-alkoxy) thiocarbonyl or C? -Cg-alkyl, which may be substituted by cyano, C? -C6-alkoxy, C-C6-alkylthio, (C? -C6-alkoxy) carbonyl, (C? -C6-alkylamino) carbonyl, Di (C? -C6-alkyl) aminocarbonyl or (Cx) -Cß-alkyl) carbonyloxy; Z a chemical bond, oxygen, sulfur, -S (O) -, -S (0) 2-, -NH- or -N (R8) -; R7 and R8 each independently of the other, qu o, c ano-? -4-a,? - - -? - 4-, C? -C4-halogenoalkoxy-C? -C4-alkyl, C3-C4-alkenyloxy- C? -C4-alkyl, C3-C4-alkynyloxy-C? -C4-alkyl, C3-C8-cycloalkoxy-C? -C4-alkyl, amino-C? -C4-alkyl, C? -C4-alkylamino -C? -C -alkyl, di (C? -C4-alkyl) amino-C? -C4-alkyl, C? -C4-alkylthio-C? -C4-alkyl, C? -C4-haloalkylthio-C? C4-alkyl, C3-C4-alkenylthio-C? -C4-alkyl, C3-C4-alkynylthio-C? -C4-alkyl, C? -C4-alkylsulfinyl-C? -C4-alkyl, C? -C4-halogenoalkylsulfinyl -C? -C4-alkyl, C3-C4-alkenylsulfinyl-C? -C4-alkyl, C3-C4-alkynylsulfinyl-C? -C4-alkyl, C? -C4-alkylsulfonyl-C? -C4-alkyl, C? -C4-halogenoalkylsulfonyl-C? -C4-alkyl, C3-C4-alkenylsulfonyl-C? -C4-alkyl, C3-C4-alkynylsulfonyl-C? -C4-alkyl, C3-Cg-alkenyl, cyano- C3-Cg-alkenyl, C3-C6-haloalkenyl, C3-Cg-alkynyl, cyano-C3-Cg-al-quinyl, C3-Cg-haloalkynyl, hydroxycarbonyl-C? -C4-alkyl, (C? -C4-alkoxy) carbonyl-C? -C4-alkyl, (C? -C4-alkylthio) carbonyl-C? C4-alkyl, aminocarbonyl-C? -C -alkyl, (C? -C4-alkylamino) carbonyl-C? -C4-alkyl, di (C? -C4-alkyl) aminocarbonyl-C? -C4-alkyl, di ( C? -C4-al-quil) -phosphonyl-C? -C4-alkyl, C3-C8-cycloalkyl, C3-C8-C-C4-cycloalkyl-alkyl, phenyl, phenyl-C? -C4-alkyl, heterocyclyl to 7 members or heterocyclyl-C? -C4-alkyl, each heterocyclyl ring can contain a carbonyl or thiocarbonyl ring member, and each cycloalkyl, phenyl and heterocyclyl ring can be unsubstituted or carry from one to four substituents, each selected from the a group comprising cyano, nitro, amino, hydroxy, carboxy, halogen, C? -C4-alkyl, C? -C4-haloalkyl, C? -C4-alkoxy, C? -C4-halogenoalkoxy, C? -C4-alkylthio, C? -C4-haloalkylthio, C? -C4-alkylsulfonyl, C? -C4-haloalkylsulfo-nyl, (C? -C4-alkoxy) carbonyl, (C? -C4-alkyl) carbonyl, (C? -C4) -halogenalkyl) carbonyl, (C? -C4-alkyl) carbonyloxy, (C? -C4-haloalkyl) carbonyloxy and di (C? -C4-al-quil) amino, or, whenever Z means a chemical bond, R7 can mean, if desired, also hydrogen, hydroxy, cyano, mercapto, amino, halogen, -CH (OH) -CH2-R9 -CH (halogen) -CH2-R9 , -CH-CH (halogen) -R9, -CH = CH-R9 O -CH = C (halogen) -R9, where? -4-,,? -4-lamino) carbonyl or di (C? -C4) -alkyl) aminocarbonyl, or R7 and R8 together form a chain of 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene, which may in each case be unsubstituted or carry one to four C? -C4 alkyl groups or one or two groups ( C? -C -alkoxycarbonyl; as well as the salts useful in the agriculture of the compounds i. 3- (Benzazol-4-yl) pyrimidinedione derivatives of the formula I according to claim 1, wherein X is oxygen, R 1 is hydrogen, amino or C? -Cg-alkyl, R 2 is hydrogen, halogen, C? -C6 -alkyl, C? -Cg-haloalkyl or C? -Cg-alkylsulfonyl, R3 is hydrogen, R4 is hydrogen, fluorine or chlorine, R5 is cyano or halogen and R6 is C? -Cg-alkyl, C3-Cg-alkynyl, C? -Cg-alkylsulphonyl or (C? -Cg-alkoxy) carbonyl. Use of the 3- (benzazol-4-yl) pyrimidinedione derivatives I and their salts useful in agriculture according to claim 1 as herbicides. Herbicidal products containing a herbicidal active amount of at least one 3- (benzazol-4-yl) pyrimidinedione derivative of the formula I or a salt of I according to claim 1 and at least one support liquid and / or solid, as well as, if desired, at least, a tenso-active substance. Process for obtaining herbicidal products, characterized in that a herbicidal active quantity of at least one derivative of 3- (benzazol-4-yl) pyrimidinedione of the formula I or a salt of I according to claim 1 is mixed, and at least one liquid / solid support, as well as, if desired, at least one surfactant substance. Procedure to control the. growth of indeterminate plants, characterized in that an active herbicidal amount of at least one derivative of 3- (benzene) is made to act on the plants, their living space or the seeds. SUMMARY OF THE INVENTION Derivatives of 3- (benzazole) -4-yl) pyrimidinedione I and its salts, where X O, S; R1 H, NH2 / C? -Cg-alkyl, C? -Cg-haloalkyl; R2 H, halogen, C? -Cg-alkyl, C? -Cg-haloalkyl, C? -Cg-alkylthio, C? -Cg-alkylsulfinyl, C? -C6-alkylsulphonyl; R3 H, halogen, C? -Cg-alkyl; R4 H, halogen; R5 CN, halogen, C6-C6-alkyl, C6-C6-haloalkyl, C6-C6-alkoxy, C6-C6-haloalkoxy; _? _ = one group = N-N (R6) -, = C (ZR7) -N (R6) -, = C (ZR7) -0-, = C (ZR7) -S-; R6 = _C? -Cg-alkyl, C? -C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-Cg-alkynyl, C? -Cg-alkyl-S02, C? -C6 -alkyl-CO, C? -C6-haloalkyl-CO, C? -C6 -alkyl-CS, C? -C6-alkoxy-CO, C? -C6-alkoxy-CS or Cx-Cg-optionally substituted alkyl; chemical bond, 0, S, -S (0) -, -S0 -, -NH-, -N (R8) -; R7, R8 = C? -Cg-alkyl, C? -Cg-haloalkyl, hydroxy-C? -C -alkyl, cyano-C? -C4-alkyl, C? -C4-alkoxy-C-C4-alkyl , C? -C4-haloalkoxy-C? -C -alkyl, C3-C4-alkenyloxy-C? -C4-alkyl, C3-C4-alkynyloxy-C? -C4-alkyl, a re vn cac n. Arylureas of the formula III wherein L2 means C? -C4-alkyl or phenyl and Ri-R5 as well as Y have the meanings indicated in claim 1. Arylamilides of the formula IV wherein L2 means C? -C4-alkyl or phenyl and Ri-R5 as well as Y have the meanings indicated in claim 1.
  2. 2-Aminophenols, substituted -thiophenols and substituted -anilines of the formula V wherein the variables X and R-R6 have the meanings indicated in claim 1. - - -? - 4-,? - - - C -C -alkyl, C? -C4-alkylthio-C? -C -alkyl, C? -C -haloalkylthio-C? -C4 -alkyl, C
  3. 3-C
  4. 4- alkenylthio-C?-C4-alkyl, C3-C4-alkynylthio-C?-C4-alkyl, C?-C4-alkylsulfinyl-C?-C4-alkyl, C?-C4-halogenoalkylsulfinyl-C?-C4- alkyl, C3-C4-alkenylsulfinyl-C? -C4-alkyl, C3-C4-alkynylsulfinyl-C? -C4-alkyl, C? -C4-alkylsulfonyl-C? -C4-alkyl, C? -C4-haloalkylsulphonyl -C? -C4-alkyl, C-C4-alkenylsulfonyl-C? -C-alkyl, C3-C4-alkynylsulfonyl-C? -C -alkyl, C3-Cg-alkenyl, cyano-C3-Cg-alkenyl, C3- Cg-halogen-alkenyl, C3-Cg-alkynyl, cyano-C3-Cg-alkynyl, C3-C6-haloalkynyl, HO-CO-C? -C4-alkyl, (C? -C4-alkoxy) C0-C C4-alkyl, (C? -C4-alkyl) CS-C? -C4-alkyl, H2N-CO-C? -C4-alkyl ?, C? -C4-alkyl-NHC0-C? -C4-alkyl , di (C? -C4-alkyl) NCO-C? -C4-alkyl, di (C? -C4-alkyl) fos-fonyl-C? -C4-alkyl, C3-C8-optionally substituted cycloalkyl, C3-C8 -cycloalkyl-C? -C-alkyl, phenyl, phenyl-C? -C4-alkyl, heterocyclyl or heterocyclic il-C? -C4-alkyl of 3 to 7 members, each heterocyclyl ring being able to contain an annular member of CO or CS, or, if Z = chemical bond, then R7 also means H, OH, CN, SH, NH2, halogen, -CH (OH) -CH2-R9, -CH (halogen) -CH2-R9, -CH2-CH (halogen) ) -R9, -CH = CH-R9 or -CH = C (halogen) -R9, where R9 = COOH, (C? -C4-alkoxy) carbonyl, (C? -C-alkylthio) carbonyl, C0NH2, C? -C4-alkyl-NHCO or di (C? -C4-alkyl) NCO, or R7 + R8 = a chain of optionally substituted 1,3-propylene, tetramethylene, penta-methylene or ethyleneoxyethylene.
MXPA/A/2000/005040A 1997-12-17 2000-05-23 Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives MXPA00005040A (en)

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DE19755926.3 1997-12-17

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