MXPA00010270A - Substituted (4-brompyrazole-3-yl)benzazoles - Google Patents

Abstract

The invention relates to substituted (4-brompyrazole-3-yl)benzazoles of the formula (I), and their salts, where Z is -N=C(XR6)-O- or -N=C(XR6)-S-, which via the nitrogen, oxygen or sulphur are bound to&agr;;and X=a chemical bond, oxygen, sulphur, -S(O)-, -SO2-, -NH- or -N(R7)-. The invention also relates to the use of said substances as herbicides, notably for the desiccation/defoliation of plants.

Description

(4-BROMOPI AZOL-3-IL) SUBSTITUTE BENZAZOLES The present invention relates to novel substituted (4-brsmopyrazol-3-yl) benzazole compounds of formula I in which the variables have the following meanings: R 'hydrogen, C, -C, -alkyl or C, -C 4 -haloalkyl; Rs cyano, C, -C, -alkyl, C, -C 4 -haloalkyl, C, -C 4 -alkoxy, C, -C 4 -haloalkoxy, C, -C, -alkylthio, C, -C 4 -haloalkylthio, Cj-C-alkylsulfinyl, C, -C 4 -haloalkylsulfyl, C, -C, -alkylsulfonyl or -Cj-halogenoalkylsulfonyl; R * hydrogen or halogen; Rs hydrogen, halogen, cyano, C, -C 4 -alkyl, C, -C 4 -halogenalkyl, C, -C 4 -alkoxy or Cj-C-haloalkoxy; X a chemical bond, oxygen, sulfur, -S (0) -, -S02-, -NH- or -N (R '); R6, R ', independently of each other Cj-Cj-alkyl, C, -Cβ-haloalkyl, cyano-C1-C4-alkyl, hydroxy-C3-C4-alkylo, C3-C3-alkenyl, Cyan-C3-C6- alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, cyano-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C, -halogen-alkoxy -C1-C4-alkyl, Cj-Cj-alkenyloxy-Cj-Cj-alkyl, C3-C4-alkynyloxy-C1-C4-alkyl, C3-Cß-cycloalkyloxy-Cj-C4 -alkyl, amino-C3-C4- alkyl, C1-C4-alkylamino-C1-C4-alkyl, di (C3-C4-alkyl) amino-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C, -C4-haloalkylthio-C1 -C4-alkyl, Cj-C-alkenylthio-Cj-Cj-alkyl, C3-C4-alkynylthio-C1-C4-alkyl, C1-C4-alkylsulfinyl-C1-C4-alkyloyl, Cj-C-haldgenoalkylsulfinyl - ^ - C.-alkyl, C3-C4-alkenyl-sulphonyl-C3-C4-alkyl, C3-C4-alkynylsulfyl-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, C, -C, -halogenoalkyl 1 sulfonyl -C3-C4-alkyl, C3-C, -alkenylsulfonyl-C1-C4-alkyl, C3-C4-alkynylsulfonyl-Cj-C, -alkyl, hydroxycarbonyl-C, - C4 -alkyl, (C1-C4-alkoxy) carbonyl-C1-C4-alkyl, which may carry a cyano or (C1-C4-alkoxy) carbonyl group, (C3-C4-alkylthio) carbonyl-C? -C4-alkyl , C3-C4-aminocarbonyl-alkyl, Cj-Cj-alkylaminocarbonyl-C1-C4-alkyl, di (C1-C4-alkyl) -aminocarbonyl-C1-C4-alkyl, alkyl, C3-Cβ-cycloalkyl-C, -C 4 -alkyl, phenyl, phenyl-C, -C 4 -alkyl, heterocyclyl or heterocyclic-Cj-C 4 -alkyl 3 to 7 links, wherein each cycloalkyl ring and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring link, and wherein each cycloalkyl, phenyl or heterocyclyl ring may be unsubstituted or may carry from one to four substituents, each selected from the group consisting of in cyano, nitro, amino, hydroxy, carboxy, halogen, C1-C4-alkyl, Cj-C4-haloalkyl, Cj-Cj-alkoxy, C ^ C ^ haloalkoxy, C, -C4-alkylthio, C1-C4-haloalkylthio, Cj-C4-alkylsulfonyl, Cj-C, - halogenoalkylsulfonyl, (C1-C4-alkoxy) carbonyl, (C, -C4-alkyl) carbonyl, (C1-C4-haloalkyl) carbonyl, (C3-C4-15 alkyl) carbonyloxy , carbonyloxy and di (C, -C4-alkyl) amino; as long as X is a chemical bond, oxygen, sulfur, - NH- or -N (R7) -, Rs can also mean (CrC (- 2o alkyl) carbonyl, (C1-C4-haloalkyl) carbonyl, (Cj-C , - alkoxycarbonyl, Cj-Cj-alkylsulfonyl or C, -C4-halogenoalkylsulfonyl; as long as X is a chemical bond, R6 can also signify hydrogen, cyano, mercapto, amino, halogen, -CH, -CH (halogen) -R ", -CH = CH-R8 or , < fc * - * » -CH = C (halogen) -R ", where R * represents hydroxycarbonyl, (C, -C4-alkoxyl) carbonyl, (C1-C4-alkyltol) carbonyl, aminocarbonyl, Cj-C4-alkylaminocarbonyl , di (C, -C4-alkyl) aminocarbonyl or di (Cj-C-alkyl) phosphonyl, or R6 and R 'together represent a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain, which respectively can be unsubstituted or can carry from one to four 0, -C, -alkyl groups or one or two (C1-) groups C, -alkoxycarbonyl, as well as agriculturally utilizable salts of these compounds I. Furthermore, the invention relates to the use of the compounds I as herbicides and / or for the drying / defoliation of plants, herbicidal compositions and compositions for drying and / or defoliation of plants, which contain the compounds I as active substances, processes for the preparation of the compounds I and of herbicidal compositions and compositions for the desiccation / defoliation of plants, using the compounds I, procedures to combat the unspotted growth of plants and for the desiccation / defoliation of plants with the compounds I, as well as new intermediate compounds of the formulas Va and Vb. group of the general formula of active substances which are the subject of the oldest application DE-A 19 652 240.

DESCRIPTION OF THE INVENTION The present invention is based on the objective of providing new pyrazole compounds of herbicidal effect with which undesired plants can be better and selectively controlled, than with the known compounds. The objective also extended to the provision of new compounds with a desiccant / defoliant effect. Thus, those present (substituted 4-bromopyrazol-3-ylbenzazoles of formula I) were found. In addition, herbicidal compositions containing the compounds I and possessing a very good herbicidal effect were found, as well as methods for the preparation of these compositions and methods for combating them. undesired growth of plants with compounds I. It was further found that compounds I are also suitable for drying / defoliation of parts of plants, for which crop plants such as cotton, potato, rapeseed, sunflower, beans soybeans or field beans, especially cotton In this regard, compositions for the desiccation and / or defoliation of plants, methods for preparing said compositions and methods for desiccation and / or defoliation of plants with compounds I were found. then in the form of mixtures of enantiomers or diastereoisomers. In compounds with at least one olefinic residue, E- / Z isomers are also possible, if appropriate. Both the pure enantiomers or diastereomers and their mixtures are the object of the invention. The parts of organic molecules listed in the definition of substituents R1, R! and R5 to R "or as residues in cycloalkyl, phenyl or heterocyclic rings, represent collective concepts, such as the halogen meaning, for the individual enumerations of the members of the groups, all the carbon chains, that is, all the alkyl radicals , haloalkyl, cyanoalkyl, oxyalkyl, aminoalkyl, oxycarbonylalkyl, aminocarbonylalkyl, phosphonylalkyl, oxyamyalkyl, phenylalkyl, heterocyclylalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, halogenalkynyl and cyanoalkynyl can be straight or branched chain. to five identical or different halogen atoms The halogen meaning respectively represents fluorine, chlorine, bromine or iodine, in addition, for example: Cj-Cj-alkyl represents: CH3, C, H5, n-propyl, CH (CH3) i; n-butyl, 1-methylpropyl, 2-methylpropyl or C (CH 3) 3; C3-C4-haloalkyl represents: a C1-C4-alkyl residue, as Example, CH2F, CHF, CF, CH2C1, CH (C1) 2, C (C1), chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, , 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-C: F5, CF2-C2FS, 1- (fluomethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, -fluorbutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorbutyl; C3-Cβ-alkyl represents: Cj-C4-alkyl, as mentioned above, as also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1,2-d? met? l-propyl, 1-methylpentyl, 2-methyl? -pentyl, 3-methyl? -pentyl, 4-methylpentyl, 1, 1-d? methylene, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-di-ethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 , 1, 2-t-methyl-l-pyl, 1,2,2-trimethylpropyl, 1-yl-methylpropyl or l-ethyl-2-ethylpropyl, preferably CH3, C2H5, CHj-C2H5, CH (CHj) j, n-butyl, C (CH 3) 3, n-pentyl or n-hexyl; - «- - •«. .2g-. ~ .- **? * - »* it was mentioned above, that it is partially or totally replaced by fluorine, chlorine, bromine and / or iodine, ie, for example, one of the residues mentioned for C, -C4-haloalkyl, as well as S-fluorine-1-pentyl, 5-chloro-l-pentyl, 5-bromo-l-pentyl, 5-iodo-l-pentyl, 5, 5, 5-trichloro-1-pentyls, n-CsF ,,, 6-fluoro-1-hex? it, 6-chloro-l-hexyl, 6-bromo-1-hexyl, 6-iodo-l-hexyl, 6,6-6-trichloro-l-hexyl or do-decafluorhexyl; cyano-C1-C4-alkyl represents: CH2CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyano-l-propyl, 2-c? ano-l-prspilo, 3-cyano-l-propyl, 1-cyano-l -butyl, 2-cyano-l-butyl, 3-cyano-l-butyl, 4-cyano-l-butyl, l-cyano-2-butyl, 2-cyano-2-butyl, 3-cyano-2-butyl , 4-cyano-2-butyl, 1- (CH2CN) -1-ethyl, 1- (CH2CN) -1- (CH3) -1-ethyl or 1- (CH2CN) -1-propyl; hydroxy-C3-C4-alkyl represents: CH2OH, 1-hydroxyl ethanol, 2-hydroxyethyl, 1-hydroxy-1-propyl, 2-hydroxy-1-propyl, 3-hydroxy-1-propyl, -hydroxy-l-butyl, 2-hydroxy-l-butyl, 3-hydroxy-1-butyl, 4-hydroxy-l-butyl, l-hydroxy-2-butyl, 2-hydroxy-2-butyl, 3-hydroxy -2-butyl, 4-hydroxy-2-butyl, I (CH2OH) -1-ethyl, 1- (CH2OH) -1- (CH,) -1-ethyl or 1- (CH, 0H) -1-propyl; propyl, 1-am? no-l-butyl, 2-ammo-l-butyl, 3-amino-1-butyl, 4-amino-1-butyl, l-amino-2-butyl , 2-am? No-2-butyl, 3-apuno-2-butyl, 4-amino-2-butyl, 1- (CH, NH2) -1-ethyl, 1- (CH2NH2) -1 - (CH 3) -1-ethyl or 1- (CH 2 NH 2) -1-propyl; hydroxycarbonyl-C3-C4-alkyl represents: CH2COOH, l- (COOH) -ethyl, 2- (COOH) ethyl, 1- (COOH) -1-propyl, 2- (COOH) -1-propyl, 3- (COOH) ) -l-propyl, 1- (COOH) -1-butyl, 2- (COOH) -1-butyl, 3- (COOH) -1-butyl, 4- (COOH) -1-butyl, 1- (COOH) ) -2-butyl, 2- (COOH) -2-butyl, 3- (COOH) -2-butyl, 4- (COOH) -2-butyl, 1- (CH2COOH) -1-ethyl, 1- (CH2C00H) -1- (CH3) -1-ethyl or 1- (CH2COOH) -1-propyl; aminocarbsnil-C1-C4-alkyl represents: CH2CONH2, 1- (CONH2) ethyl, 2- (CONH2) ethyl, 1- (CONH2) -1-propyl, 2- (CONH2) -1-propyl, 3- ( CONH2) -1-propyl, 1- (CONH2) -1-butyl, 2- (CONH2) -1-butyl, 3- (CONH2) -1-butyl, 4- (CONH2) -1-butyl, 1- ( CONH2) -2-butyl, 2- (CONH2) -2-butyl, 3- (CONH2) -2-butyl, 4- (CONH2) -2-butyl, 1- (CH2CONH2) -1-ethyl, 1- ( CH2CONH2) -1- (CH,) -1-ethyl or 1- (CH2CONH2) -1-propyl; phenyl-C1-C4-alkyl represents: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenyl-1-propyl, 2-phenyl-1-propyl, 3-phenyl-1-propyl, 1-phenyl-1- Butyl, 2-phenyl-1-butyl, 3-phenyl-1-butyl, (methyl) -1-ethyl or 1- (benzyl) -1-propyl, preferably benzyl or 2-phenylethyl; Heterocyclic-C, -C 4 -alkyl represents: heterocyclylmethyl, 1-heterocyclyl-ethyl, 2-heterocyclic-ethyl, 1-heterocyclyl-1-propyl, 2-heterocyclyl-1-propyl, 3-heterocyclyl- l-propyl, 1-heterocyclyl-1-butyl, 2-heterocyclyl-1-butyl, 3-heterocyclyl-1-butyl, 4-heterocyclyl-1-butyl, 1-heterocyclyl- 2-butyl, 2-heterocyclyl-2-butyl, 3-heterocyclyl-2-butyl, 3-heterocyclyl-2-butyl, 4-heterocyclyl-2-butyl, 1- (heterocyclylmethyl) -1-ethyl, 1- (heterocyclylmethyl) ) -1- (methyl) -1-ethyl or 1- (heterocyclylmethyl) -1-propyl, preferably heterocyclylmethyl or 2-heterocyclyl-ethyl; C1-C4-alkoxy represents: OCH, OC2H5, 0-CH2-C2H5, OCH (CH,) 2, n-butoxy, OCHICH,) -C2HS, OCH2-CH (CH,) 2 or OC (CH,), , preferably OCH, OC2H5 or OCH (CH,) 2; Cl-C4-halogenoalkoxy represents: a C1-C4-alkoxy radical, as mentioned above, which is partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, OCH2F, OCHF2, OCF ,, OCH2Cl, 0CH (C1) 2, 0C (C1), chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2? Odoethoxy, 2, 2-difluorethoxy, 2.2.2 -trifluoretoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoro- fluorpropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-di-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3, 3, 3-trifluorpropoxy, 3, 3, 3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 - (CH2F) -2-fluoro-ethoxy, 1- (CH2C1) -2-chloroethoxy, 1- (CH2Br) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or non-nafluorobutoxy, preferably OCHF2 , OCF ,, dichlorof luormetoxí, chlorodifluormetoxi or 2, 2, 2-trif luoretoxi; C, -C4-alkylthio represents: SCH ,, SC2H5, SCH2-C2H5, SCH (CH,) 2, n-butylthio, 1-methylpropylthio, SCH2-CH (CH,) 2 or SC (CH,), preferably SCH , or SC2H5; C, -C4-haloalkylthio represents: a C, -C4-alkylthio residue as mentioned above, which is partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, SCH2F, SCHF2, SCF, SCH2C1, SCH (C1) 2, SC (C1), chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluor ethylthio, 2-fluoroethylthio, 2-chloroetyltin, 2-bromoetyl, 2-? Odoet? Lt? O, 2, 2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoro-tiltio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, SC2FS, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropyl, 2-bromopropylthio, 3-bromopropyl. or, 3, 3, 3-trifluoropropylthio, ^ ¡^ G tiltium, 4-fluorbutylthio, 4-chlorobutylthio, 4-bromobutylthio or SCF2-CF2-C2FS, preferably SCHF2, SCF3, dichlorofluoromethylthio, Chlorodifluoromethylthio or 2,2,2-trifluoroethylthio; C1-C4-C-alkoxy, -C4-alkyl represents: C, -C, -alkyl substituted by C, -C4-alkoxy, as mentioned above, ie, for example, CH2-OCH ,, CH2-OC2H5, n-propoxymethyl, CH2-OCH (CH,) 2, n-butoxymethyl, (1-met? lpropox?) ethyl, (2-methylpropoxy) methyl, CH2-OC (CH,) 3, 2- (methox?) etllo , 2- (ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methyloxy?) Ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2- methylpropoxy) ethyl, 2- (1,1-dimethylether) ethyl, 2- (methoxy) ropy, 2- (ethoxy) propyl, 2- (n-propoxypropyl, 2- (1-methylethoxy) propyl 2- (n-butoxy) propyl, 2- (l-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1,1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (n-propoxy) propyl, 3- (l-methyletoxy) propyl, 3- (n-butoxy) propyl, 3- (1-methylpropoxy) propyl, 3- (2-methopropoxy) propyl, 3- (1, 1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (n-propoxy) butyl, 2- (1-methylethoxy) butyl, - (n-butoxy) butyl, 2- (methylpropoxy) butyl, 2- (2-methyl) t-propoxy) butyl, 2- (1,1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (n-propoxy) butyl, 3- (1-methylethoxy) butyl, - (n-butoxy) utilo, 3- (l-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (l, l-dimethylethoxy) butyl, 4- (methoxy (butyl, 4- (ethoxy) butyl) , 4- (n- d) ethoxybutyl methy, preferably CH 2 -OCH ,, CH 2 -OC 2 H 5, 2- (OCH,) ethyl or 2- (OC 2 H 5) ethyl; C1-C4-haloalkoxy-C1-C4-alkyl represents: C, -C4-alkyl substituted by C1-C4-haloalkoxy, as previously enunciated, ie, for example, 2- (OCHF2) ethyl, 2- (OCF, ) ethyl or 2- (OC2F5) ethyl; C, -C4-alkylthio-CI-C4-alkyl: Cj-C-alkyl substituted by C, -C4-alkylthio, as mentioned above, ie, for example, CH2-SCH3, CH2-SC2HS, n-propylthiomethyl , CH2-SCH (CH3) 2, n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropyl-thiojmethyl, CH2-SC (CH3) 2, 2- (methylthio) ethyl, 2- (ethylthio) ethyl, - (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl, 2- (2-methylpropyl-thiojetyl, 2- (1,1 -dimethylethylthio) ethyl, 2- (methylthio) propyl, 2- (ethylthio) propyl, 2- (n-propylthio) propyl, 2- (1-methylethylthio) propyl, 2- (n-butylthio) propyl, 2- (1-methylpropyl-thiojpropyl, 2- (2-methylpropylthio) propyl, 2- (1,1-dimethylethylthio) propyl, 3- (methylthio) propyl, 3- (ethylthio) propyl, 3- (n-propylthio) propyl, 3- (l-methylethylthio) propyl, 3- (n-butylthio) propyl, 3- (l-methylpropylthio) propyl, 3- (2-methylpropylthio) propyl, 3- (1,1-dimethylethylthio) ) propyl, 2- (methylthio) butyl, 2- (ethylthio) butyl, 2- (n-propylthio) butyl, 2- (l-methylethylthio) butyl, 2- (n-butylthio) butyl, 2- (1-methylpropyl- propylthio) butyl, 3- (1-methylethyl) butyl, 3- (n-butyl-thiolbutyl, 3- (1-methylpropyl) butyl, 3- (2-methyl-propyl-thio) butyl, 3- (1, 1-dimeth-lettethyl) butyl, 4- (methylthio) butyl, 4- (ethylthio) butyl, 4- (n-propylthio) butyl, 4- (1-met? let? -thio) butyl, 4- (n-butylthio) butyl, 4- (1-methylpropyl) butyl, 4- (2-methylpropylthio) butyl or 4- (1, 1-dimethylethylthio) butyl , preferably CH2-SCH3, CH2-SC2H5, 2- (SCH3) ethyl or 2- (SC2H5) ethyl; C1-C4-haloalkylthio-C1-C4alkyl represents: C, -C4-alkyl substituted by C1-C4-haloalkylthio, as mentioned above, ie, for example, 2- (SCHF2) ethyl, 2- ( SCF3) ethyl or 2- (SC2F5) ethyl; (C, -C 4 -alkoxy) imino-C 1 -C 4 -alkyl represents: C, -C 4 -alkyl substituted by (C, -C 4 -alkoxy) imino, as = N-CH ,, = N-C 2 HS, = NCH2-C2H5, = N-CH (CH,) 2, = NCH2-CH2-C2H5, = NCH (CH,) -C2H5, = NCH2-CH (CH,) 2 or = NC (CH,) 3, ie , for example, CH = NCH ,, CH = N-C2H5, CH2-CH = N-CH3 or CH2-CH = N-C2H5; (C, -C4-alkyl) carbonyl represents: CO-CH ,, C0-C2H5, CO-CH2-C2H5, C0-CH (CH,) 2, n-butylcarbonyl, CO-CH (CH,) -C2H5, C0 -CH2-CH (CH,) 2 or CO-C (CH,), preferably CO-CH, or CO-C2H5; , ^. , - ^ ~ * - - ** a * «e? ^ A is partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, CO-CH2F, CO-CHF2, CO-CF ,, C0-CH2C1, C0-CH (C1) 2, CO-C (Cl) ,, chlorofluoromethylcarbonyl, dichlorofluor-methylcarbonyl, chlorodifluoromethylcarbonyl, 2-fluoro-methylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoro-ethylcarbonyl, 2,2,2-trifluoro-ethylcarbonyl, 2-chloro -2-fluorocarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoro-ethylcarbonyl, 2,2,2-trichloroethylcarbonyl, CO-C2Fs, 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, C0-CF2-C2F5, l- (CH2F) -2-fluorocarbonyl, 1- (CH2C1) -2-chloroethylcarbonyl, 1- (CH2Br) -2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl , 4-bromobutyl rbonyl or nonafluorbutylcarbonyl, preferably C0-CF3, C0-CH2C1, or 2,2,2-trifluoroethylcarbonyl; (Cj-Cj-alkylJcarbonyloxy represents: 0-CO-CH ,, 0-CO-C2Hs, 0-C0-CH2-C2HS, 0-C0-CH (CH,) 2, 0-C0-CH2-CH2-C2H5, 0-CO-CH (CH,) -C2H5, 0-CO-CH2-CH (CH3) 2 or 0-C0-C (CH,) 3, preferably 0-C0-CH3 or 0-C0-C, H « : is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, 0-CO-CH2F, 0-CO-CHF2, 0-C0-CF3, 0-CO-CHjCl, 0-CO- CH (Cl) 2, 0-CO-C (Cl) 3, chlorofluoromethylcarbonyloxy, dichlorofluoromethylcarbonyloxy, chlorodifluoromethylcarbonyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2, 2, 2-trifluoro-ethylcarbonyloxy, 2-chloro-2-fluoro-ethylcarbonyloxy, 2-chloro-2,2-difluoro-ethylcarbonyloxy, 2,2-dichloro-2-fluoro-ethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, 0-C0-C2F5, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3, 3, 3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, 0-CO-CH2-C2F5, 0-C0-CF2-C2F5, 1- (CH2F) -2-fluoro-ethylcarbonyloxy, 1- (CH2C1) -2- chloroet? lcarbomlo- xi, 1- (C H2Br) -2-bromoethylcarbomloxy, 4-fluorobutylcarbomloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluor-butylcarbonyloxy, preferably 0-CO-CF, 0-CO-CH2Cl or 2,2,2-trifluoro-ethylcarbonyloxy; (C, -C 4 -alkoxy) carbonyl represents: CO-OCH 3, CO-OC 2 H 5, n-propoxycarbonyl, CO-OCH (CH 3) 2, n-butoxycarbonyl, CO-OCH (CH 3) -C 2 H 5, CO-OCH 2 -CH ( CH3) 2 or CO-OC (CH3) 3, preferably CO-OCH, or ^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^ (0, -0, -3100 1) carbonyl-C, -C4-alkyl represents: C, -C4-alkyl substituted by (C ^ Cj-alkoxy) carbonyl, as mentioned above, ie, for example, CH2- CO-OCH3, CH2-C0-OC2H5, n-propoxycarbonyl-methyl, CH2-C0-0CH (CH3) 2, n-butoxycarbonylmethyl, CH2-C0-0CH (CH3) -C2HS, CH2-CO-OCH2-CH (CH3) 2, CH2-C0-OC (CH3) 3, 1- (methoxycarbonyl) ethyl, 1- (ethoxycarbonyl) ethyl, 1- (n-propoxycarbonyl) ethyl, 1- (1-methylethoxycarbonyl) ethyl, 1- ( n-butoxycarbonyl) ethyl, 2- (methoxycarbonyl) ethyl, 2- (ethoxycarbonyl) ethyl, 2- (n-propoxycarbonyl) ethyl, 2- (1-Methylethoxy-carbonyl) ethyl, 2- (n-butoxycarbonyl) ethyl, 2- (1-methylpropoxy-carbonyl) ethyl, 2- (2-methylpropoxycarbonyl) ethyl, 2- (1,1-dimethylethoxycarbonyl) ethyl, 2- (methoxycarbonyl) propyl, 2- (ethoxycarbonyl) propyl, 2- (n-propoxycarbonyl) propyl, 2- (l-methylethoxycarbonyl) propyl, 2- (n-butoxycarbonyl) propyl, 2- (l-methylpropoxycarbonyl) ropyl, 2- (2-methylpropoxycarbonyl) pro-phenyl, 2- (1, 1-dimethylethoxycarbonyl) propyl, 3- (methoxycarbonyl) -propyl, 3- (ethoxycarbonyl) propyl, 3- (n-propoxycarbonyl) propyl, 3- (1-methylethoxycarbonyl) propyl, 3- (n-butoxycarbonyl) propyl, 3- (1-methylpropoxycarbonyl) propyl, 3- (2-methylpropoxycarbonyl) propyl, 3- (1, 1-dimethylethoxycarbonyl) propyl, - (methoxy-carbonyl) butyl, 2- (ethoxycarbonyl) butyl, 2- (n-propoxycarbonyl) butyl, 2- (1-methylethoxycarbonyl) butyl, 2- (n-butoxycarbonylbutyl, 2- (1-methylpropoxycarbonyl) butyl, 2- (2-methylpropoxycarbonyl) butyl, 2- (1, l-dimethylethoxycarbonyl) butyl- , - -, - butoxycarbonyl) butyl, 3- (1-methylpropoxycarbonyl) butyl, 3- (2-methylpropoxycarbonyl) butyl, 3- (1,1-dimethylethoxycarbonyl) butyl, 4- (methoxycarbonyl) butyl, 4- (ethoxycarbonyl) butyl, 4- (n-propoxycarbonyl) butyl, 4- (1-methylethoxycarbonyl) butyl, 4- (n-butoxycarbonyl) butyl, 4- (1-methylpropoxycarbonyl) butyl, 4- (2-methylpropoxcarbonyl) butyl or 4- (1,1-dimethylethoxycarbonyl) butyl, preferably CH 2 -CO-0CH 3, CH 2 -CO-OC 2 H 5, 1- (methoxycarbonyl) ethyl or 1- (ethoxycarbonyl) ethyl; (C, -C4-alkylthio) carbonyl represents: CO-SCH ,, C0-SC2Hs, C0-SCH2-C2H5, C0-SCH (CH,) 2, CO-SCH2CH2-C2H5, CO-SCH (CH,) -C2H5 , C0-SCH2-CH (CH,) 2 or CO-SC (CH,), pref erentient CO-SCH, or CO-SC2H5; (C1-C4-alkylthio) carbonyl-C1-C4-alkyl represents: C, -C4-alkyl substituted by (C, -C4-alkylthio) carbonyl, as mentioned above, ie, CH2-C0-SCH ,, CH2 -CO-SC2H ,, CH2-C0-SCH2-C2HS, CH2-CO-SCH (CH,) 2, CH3-C0-SCH2CH2-C2HS, CH2-CO-SCH (CH,) - C2H5, CH2-CO-SCH2 -CH (CH,) 2, CH2-C0-SC (CH,) ,, 1- (CO-SCH,) ethyl, 1- (CO-SC2Hs) ethyl, 1- (CO-SCH2.C2Hs) ethyl, 1 - [CO-SCH (CH,) 2] ethyl, 1- (CO-SCH2CH2-C2Hs) ethyl, 1- [CO-SCH (CH,) -C2HS] ethyl, 1- [CO-SH2-CH (CH, ) 2] ethyl, 1- [CO-SC (CH,) 3] ethyl, 2- (CO-SCH,) ethyl, 2- (C0-SC2H5) ethyl, 2- (CO-SCH2-C2Hs) ethyl, 2 - [CO-SCH (CH3) 2] ethyl, 2- (CO-SCH2CH2-C2H5) ethyl, 2- [CO-SCH (CH3) -C2H5] ethyl, 2- [CO-SCH2- 2 s, 2 2 s,, 2 pyl, 2- (CO-SCH2CH2-C2Hs) propyl, 2- [CO-SCH (CH,) -C2H5] propyl, 2- [CO-SCH2-CH (CH,) 2 ] propyl, 2- [CO-SC (CH,),] propyl, 3- (CO-SCH,) propyl, 3- (CO-SC2Hs) propyl, 3- (CO-SCH2-C2Hs) propyl, 3- [ CO-SCH (CH,) 2] propyl, 3- (CO-SCH2CH2-C2H5) propyl, 3- [CO- SCH (CH3) -C2H5] propyl, 3- [CO-SCH2-CH (CH3) propyl, 3- [CO- SC (CH,),] propyl, 2- (CO-SCH,) butyl, 2- (CO-SC2H5) butyl, 2- (CO-SCH, -C2H5) butyl, 2- [CO- SCH (CHj) 2] butyl, 2- (CO-SCH2CH2-C2H5) butyl, 2- [CO-SCH (CH,) -C2H5] butyl, 2- [CO-SCH2-CH (CH,) 2] butyl, 2- [CO-SC (CH,) butyl, 3- (CO-SCH,) butyl, 3- (CO-SC2H5) butyl, 3- (CO-SCH2-C2Hs) butyl, 3- [CO-SCH (CH ,) 2] butyl, 3- (CO-SCH2CH2-C2H5) butyl, 3- [CO-SCH (CH,) -C2H5] butyl, 3- [CO-SCH2-CH (CH,) 2] butyl, 3- [CO-SC (CH,),] butyl, 4- (CO-SCH,) -butyl, 4- (CO-SC2H5) butyl, 4- (CO-SCH2-C2H5) butyl, 4- [CO-SCH ( CH,) 2] butyl, 4- (CO-SCH2CH2-C2H5) butyl, 4- [CO-SCH (CH,) -C2H5] butyl, 4- [CO-SCH2-CH (CH,) 2] butyl or - [CO-SC (CH,),] butyl, pre preferably CH2-CO-SCH ,, CH2-CO-S2Hs, 1- (CO-SCH,) ethyl or 1- (CO-SC2Hslethyl ?; C, -C4-alkylsulfinyl represents: SO-CH ,, SO-C2H5, SO-CH2-C2H5, SO-CH (CH,) 2, n-butylsulphinyl, SO-CH (CH,) -C2H5, SO-CH2-CH (CH,) 2 or SO-C (CH,) 3, preferably SO-CH3 or SO- C2H5; C, -C 4 -haloalkylsulfonyl represents: a C, -C 4 -alkylsulfinyl radical, as mentioned above, which is partially or totally substituted by fluorine, chlorine, bromine and / or 2, 3,, tilsulfinyl, chlorodifluoromethylsulfinyl, 2-fluorethylsulphinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulphinyl, 2,2,2-tri-fluoro-sulestulphsulfinyl, 2-chloro-2-fluorethylsulphinyl, -chloro-2,2-difluoro-ethylsulfinyl, 2,2-dichloro-2-fluoro-methyl-sulfinyl, 2,2,2-trichloro-ethyl-sulfinyl, S0-C2Fs, 2-fluoropropyl-sulfinyl, 3-fluoropropyl-sulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoryl -propylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2,3-dichloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3,3,3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, SO-CH2-C2F5, SO -CF2-C2F5, 1- (CH2F) -2-fluoro-methyl-sulfinyl, 1- (CH2C1) -2-chloroethylsulfinyl, 1- (CH2Br) -2-bromoethylsulfinyl, 4-fluorbutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorbutylsulfinyl , preferably SO-CF3, S0-CH2C1 or 2,2,2-trifluoromethyl-sulfinyl; C1-C4-alkylsulfinyl-C1-C4-alkyl represents: C, -C4-alkyl substituted by Cl-C4-alkylsulfinyl, as mentioned above, ie, for example, CH2SOCH, CH2SOC2H5, n-propylsulfinylmethyl, CH2SOCH (CH, ) 2, n-butylsulfinylmethyl, (1-methylpropylsulfiniD ethyl, (2-methylpropylsulfinyl) methyl, (1,1-dimethylethylsulfinyl) methyl, 2-methylsulfinylethyl, 2-ethylsulfinylethyl, 2- (n-propylsulfinyl) ethyl, 2- (1 -methylethyl-sulfinyl) ethyl, 2- (n-butylsulfinyl) ethyl, 2- (1-methylpropyl- , 3, 3, - (SOC2H5) propyl, 3- (SOC2H5) ropyl, 3- (propylsulfinyl) propyl, 3- (butylsulfinyl) propyl, 4- (SOCH,) butyl, 4- (SOC2H5) butyl, 4- ( n-propyl-sulfini-Butyl or 4- (n-butylsulfini-Butyl, especially 2- (SOCHj) ethyl; C, -C 4 -haloalkylsulfinyl-C 1 -C 4 -alkyl represents: C, -C 4 -alkyl substituted by C 4 C 2 -haloalkylsulfinyl, as mentioned above, ie, for example, 2- (2,2,2-trifluoromethyl-sulfinyl) ethyl; C, -C4-alkylsulfonyl represents: S02-CH3, S02-C2H5, CH2-C2H5-S02, 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-C2Hs; Ci-Cj-halogenoalkylsulfonyl represents: a C, -C 4 -alkylsulfonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, S02-CH2F, S02- CHF2, S02-CF3, S02-CH2C1, S02-CH (C1) 2, SOJ-C (Cl) ,, clorofluormetilsulfonilo, diclo-rofluor ethylsulfonyl, clorodifluormetilsulfonilo, 2-fluore-tilsulfonilo, 2-chloroethylsulfonyl, 2-bromoetilsulfonilo, 2 -iodoethylsulfonyl, 2,2-difluoroethylsulphonyl, 2,2,2-trifluorethylsulfonyl, 2-chloro-2-fluoro-sulfosulphonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoro-sulfosulfonyl, 2,2 ,2- propylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2,3-dicloropropilsulfonilo, 2-bromopropilsulfon? I, 3-bromopropilsulfonilo, 3, 3, 3-TRIF luorpropilsulfonilo, 3,3,3-tpcloropropilsulfonilo, S02-CH2-C2F5 , S02-CF2-C2FB, 1- (luormetil f) -2-fluoretilsulfonilo, 1- (chloromethyl) -2-cloroe-tilsulfonilo, 1- (bromomethyl) -2-bromoetilsulfonilo, 4-fluorbu-tilsulfonilo, 4-clorobutilsulfonilo, 4-bromobutylsulfonyl or nonafluorbutylsulfonyl, preferably S02-CH2C1, S02-CF3, or 2,2, 2-trifluorosulfosyl onyl; C1-C4-alkylsulfonyl-C1-C4-alkyl represents: C, -C4-alkyl substituted by C, -C4-alkylsulfonyl, as mentioned above, ie, for example, CH2S02-CH3, CH2S02-C2Hs, CH2S02 -CH2-C2H5, CH2S02-CH (CH3) 2, CH2CH2-C2H5-CH2S02, (1-metilpropilsul-foniDmetilo, (2-metilpropilsulfonil) methyl, CH2S02-C (CH3) 3, CH (CH3) S02-CH3, CH (CH3) S02-C2H5, CH2CH2S02-CH3, CH2CH2S02-C2H5, CH2-C2H5-CH2CH2S02, CH2CH2S02-CH (CH,) 2-CH2CH2-C2H5 CH2CH2S02, 2- (l-metilpropilsulfonil) ethyl, 2- (2- methylpropylsulfonyl) ethyl, CH2CH2S02-C (CH,) 3, 2- (S02-CH3) propyl, 2- (S02-C2H5) propyl, 2- (S02-CH2-C2HS) propyl, 2- [S02-CH (CH ,) 2] propyl, 2- (S02-CH2CH2-C2H5) propyl, 2- (l-methylpropylsulfonyl) propyl, 2- (2-methylpropyl-sulfonylpropyl, 2- [S02-C (CH3) 3] propyl, 3- (S02-CH3) propyl, 3- (S02-C2H5) propyl, 3- (S02-CH2-C2Hs) propyl, 3- [S02-CH (CH3) 2] propyl, 3- (S02-CH2CH2-C2Hs) propyl , 3- (1-methylpropylsulf or- 22 .to. a¡ -jüa > tto--? - "~ ¿& ¿ 3 3, 2 3, 2 2 5, 2 CH2-C2H5) butyl, 2- [S02-CH (CH3) 2] butyl, 2- (S02-CH2CH2-C2H5) butyl, 2- (l-methylpropylsulfonyl) butyl, 2- (2-Methylpropylsulfo-niljbutyl, 2- [S02-C (CH3) 3] butyl, 3- (S02-CH,) butyl, 3- (S02-C2H5) butyl, 3- (S02-CH2-C2Hs) butyl, 3- [S02-CH (CH,) 2] butyl, 3- (S02-CH2CH2-C2Hs) butyl, 3- (1-methylprop-lysulfonyl) butyl, 3- (2-methylpropylsulfonyl) butyl, 3- [S02- C (CH,),] butyl, 4- (S02-CH,) butyl, 4- (S02-C2H5) butyl, 4- (S02-CH2-C2Hs) butyl, 4- [S02-CH (CH,) 2 ] butyl, 4- (S02-CH2CH2-C2Hs) butyl, 4- (1-methylpropyl-sulfonyl) butyl, 4- (2-methylpropylsulfonyl) butyl or 4- [S02-C (CHj),] butyl, especially CH2CH2S02 -CH, or CH2CH2S02-C2H5; C1-C4-halogenoalkylsulfonyl-C1-C4-alkyl represents: C, -C4-alkyl substituted by C1-C4-haloalkyl sulfosyl, as mentioned above, ie, for example, 2- (2,2,2-trif) luoretilsulf onyl) ethyl; Cj-Cj-alkylamino-C ^ -C-alkyl represents: C1-C4-alkyl substituted by C1-C4-alkylamino such as NH-CH ,, -NH-C2HS, -NH-CH2-C2H5, -NH-CH (CH ,) 2, -NH-CH2CH2-C2H5, -NH-CH (CHj) C2Hs, -NH-CH2-CH (CH,) 2 and -NH-CICH,), preferably -NH-CH, or -NH- C2H5, ie, for example, CH2CH2-NH-CH, CH2CH2-N (CH,) 2, CH2CH2-NH-C2HS or CH2CH2-N (C2H5) 2; C ^ C.-Alkylaminocarbonyl represents: CO-NH-CH ,, C0-NH-C2H5, n- CH, or CO-NH-C2H5; C, -C4-alkylaminocarbonyl-C1-C4-alkyl represents: C, -C4-alkyl substituted by C1-C4-alkylaminocarbonyl, as mentioned above, preferably CO-NH-CH, or CO-NH-C2Hs, as, for example, example, CH2-CO-NH-CH ,, CH2-CO-NH-C2H5, CH2-CO-NH-CH2-C2H5, CH2-CO-NH-CH (CH,) 2, CH2-CO-NH-CH2CH2- C2H5, CH2-CO-NH-CH (CH,) -C2HS, CH2-CO-NH-CH2-CH (CH,) 2, CH2-CO-NH-C (CH,),, CH (CH,) - CO-NH-CH,, CH (CH,) -CO-NH-C2H5í 2- (CO-NH-CH,) ethyl, 2- (CO-NH-C2H5) ethyl, 2- (CO-NH-CH2- C2H5) ethyl, 2- [CH2-CO-NH-CH (CH,) 2] ethyl, 2- (CO-NH-CH2CH2-C2H5) ethyl, 2- [CO-NH-CH (CH,) -C2H5] ethyl, 2- [CO-NH-CH2-CH (CH,) 2] ethyl, 2- [CO-NH-C (CH,),] ethyl, 2- (CO-NH-CH,) propyl, 2- (CO-NH-C2H5) propyl, 2- (CO-NH-CH2-C2Hs) propyl, 2- [CH2-CO-NH-CH (CH,) 2] propyl, 2- (CO-NH-CH2CH2-C2H5 ) propyl, 2- [CO-NH-CH (CH,) -C2HS] propyl, 2- [CO-NH-CH2-CH (CH,) 2] propyl, 2- [CO-NH-C (CH,) 3] propyl, 3- (C0-NH-CH,) propyl, 3- (CO-NH-C2H5) propyl, 3- (CO-NH-CH2-C2H5) propyl, 3- [CH2-CO-NH -CH (CH3) 2] propyl, 3- (C0-NH-CH 2CH2-C2H5) prspÍlo, 3- [CO-NH-CH (CH3) -C2H5] propyl, 3- [CO-NH-CH2-CH (CH3) 2] propyl, 3- [CO-NH-C (CH, ),] propyl, 2- (CO-NH-CH,) butyl, 2- (CO-NH-C2H5) butyl, 2- (CO-NH-CH2-C2H5) butyl, 2- [CH2-CO-NH- CH (CH3) 2] butyl, 2- (CO-NH-CH2CH2-C2H,) butyl, 2- [CO-NH-CH (CH3) -C2Hs] butyl, 2- [CO-NH-CH2-CH (CH3 ) 2] butyl, 2- [CO-NH-C (CH3),] butyl, 3- (CO-NH-CH,) butyl, 3- (CO-NH-C2H5) butyl, 3- (CO-NH-) CH, -C2Hs) butyl ?, 3- [CH2-CO-NH-CH (CH,) 2] butyl, 3 - (CO-NH-CH2CH2- für ^ * ----- ** - , 4- (CO-NH-C2Hs) butyl, 4- (CO-NH-CH2-C2H5) butyl, 4- [CH2-CO-NH-CH (CH,) 2] butyl, 4- (CO-NH- CH2CH2-C2Hs) butyl, 4 - [CO-NH-CH (CH,) -C2Hs] butyl, 4- [CO-NH-CH2-CH (CH,) 2] butyl or 4- [CO-NH-C ( CH3) 3] butyl, preferably CH2-CO-NH-CH3, CH2-CO-NH-C2Hs, CH (CH3) -CO-NH-CH, or CH (CH3) -CO-NH-C2H5; di- (C, -C4-alkyl) amino represents: N (CH,) 2, N (C2H5) 2, N, N-dipropylamino, N [CH (CH,) 2] 2, N (n-C4H9) 2 , N, Nd? - (1-methyl-propiDamino, N, N-di- (2-methylpropyl) amino, N [C (CH,),] 2, N-ethyl-N-methylamino, N-methyl-N -propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-met? lpro-piDamino, N-methyl-N- (2-methylpropyl) amino, N- (1, 1-dimethyl-ethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethylDamino, N-butyl-N-ethylamino, N-ethyl -N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1,1-diethylethyl) 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- N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino, N- (1-methylethyl) -N- (2-methylpropyl) amino, N- (1, 1- dimethylethyl) -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-m) ethylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) -N- (1-methylpropiDamins or N- (1,1-dimethylethyl) -N- (2-methylpropyl) ami- di (C1-C4-alkyl) amino-C? -C4-alkyl represents: C1-C4-alkyl substituted by di (C, -C4-alkyl) -amino, as mentioned above, ie, for example, CH2N (CH,) 2, CH2N (C2HS) 2, N, N-dipropylaminomethyl, N, N-di [CH (CH,) 2] aminomethyl, N, N-dibutylaminomethyl, N, N-di- (1-methylpropyl) ) aminomethyl, N, N-di (2-methylpropyl) amomethyl, N, N-di [C (CH3) 3] aminomethyl, N-ethyl-N-methylaminomethyl, N-methyl-N-propylaminomethyl, N-methyl -N- [CH (CH 3) 2] aminomethyl, N-butyl-N-methylaminomethyl, N-methyl-N- (1-methylpropyl) aminomethyl, N-methyl-N- (2-methylpropyl) aminomethyl, N- [C (CH3) 3] -N-methylaminomethyl, N-ethyl-N-propylamino-methyl, N-ethyl-N- [CH (CH3) 2] aminomethyl, N-butyl-N-ethylamino-methyl, N-ethyl-N - (1-methylpropyl) aminomethyl, N-ethyl-N- (2-methylpropyl) aminomethyl, N-ethyl-N- [C (CH,) 3] aminomethyl, N- [CH (CH,) 2] -N- propylaminomethyl, N-butyl-N-propylaminomethyl, N- (1-methylpropyl) -N-propylaminomomethyl, N- (2-methylpropyl) -N-propylaminomethyl, N- [C (CH3) 3] -N-propylaminomethyl, N- butyl- N- (1-methylethyl) -aminomethyl, N- [CH (CH 3) 2] -N- (1-methylpropyl) aminomethyl, N- [CH (CH 3) 2] -N- (2-methylpropyl) aminomethyl, N- [C (CH3) 3] -N- [CH (CH3) 2] aminomethyl, N-butyl-N- (1-methylpropyl) aminomethyl, N-butyl-N- (2-methylpropyl) aminomethyl, N-butyl-N - [C (CH 3) 3] aminomethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminomethyl, N- [C (CH 3) 3] -N- (1-methylpropyl) aminomethyl, N- [C (CH 3) 3] -N- (2-methylpropyl) aminomethyl, N, N-dimethylaminesyl, N, N-diethylamino-ethyl, N, N-di (n-propyl) aminoethyl, N, N-di- [CH ( CH3) 2] amino- ? ta ^ ¡^^ ,,, 3 3, ethyl-N-methylaminoethyl, N-methyl-N-propylaminoethyl, N-methyl-N- [CH (CH 3) 2] aminoethyl, N-butyl-N-methylaminoethyl, N-methyl-N- ( 1-methylpropyl) aminoethyl, N-methyl-N- (2-methylpropyl) aminoethyl, N- [C (CH 3) 3] -N-methylaminoethyl, N-ethyl-N-propylaminoethyl, N-ethyl-N- [CH ( CH3) 2] aminoethyl, N-butyl-N-ethylaminoethyl, N-ethyl-N- (1-methylpropyl) aminoethyl, N-ethyl-N- (2-methylpropyl) aminoethyl, N-ethyl-N- [C (CH3 ) 3] aminoethyl, N- [CH (CH3) 2] -N-propylamino-ethyl, N-butyl-N-propylaminoethyl, N- (1-methylpropyl) -N-propylaminoethyl, N- (2-methylpropyl) -N -propylaminoethyl, N- [C (CH3) 3] -N-propylaminoethyl, N-butyl-N- [CH (CH3) 2] aminoethyl, N- [CH (CH3) 2] -N- (1-methylpropyl) aminoethyl , N- [CH (CH3) 2] -N- (2-methylpropyl) aminoethyl, N- [C (CH3) 3] -N- [CH (CH3) 2] aminoethyl, N-butyl-N- (1- methylpropyl) aminoethyl, N-butyl-N- (2-methylpropyl) -aminoethyl, N-butyl-N- [C (CH 3) 3] aminoethyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminoethyl, N- [C (CH 3) 3] -N- (1-methylpropyl) -aminoethyl or N- [C (CH 3) 3] -N- (2-methylpropyl) aminoethyl, especially N, N-dimethylaminoethyl or N, N-diethylaminoethyl; di (C1-C4-alkyl) aminocarbonyl represents: CO-N (CH3) 2, CO-N (C2H5), CO-N (CH2-C2HS) 2, CO-N [CH (CH3) 2] 2, CO- N (n-C4H9) 2, CO-N [CH (CH,) - C2H5] 2, CO-N [CH2-CH (CH3) 2] 2, CO-N [C (CH3) 3] 2, N- ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N- [CH (CH 3) 2] aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methyl- N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- [C (CH3) 3] aminocarbonyl, N - [CH (CH3) 2] -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- [C ( CH3) 3] -N-propylaminocarbonyl, N-butyl-N- [CH (CH,) 2] aminocarbonyl, N- [CH (CH,) 2] -N- (1-methylpropyl) aminocarbonyl, N- [CH ( CH 3) 2] -N- (2-methylpropyl) aminocarbsnyl, N- [C (CH 3) 3] -N- [CH (CH 3) 2] aminocarbonyl, N-butyl-N- (1-methylpropyl) aminocarbonyl, N- butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- [C (CH 3) 3] aminocarbonyl, N- (1-methylpropyl) -N- (2-methy1propyl) aminocarbonyl, N- [ C (CH3) 3] -N- (1-methylpropyl) aminocarbonyl or N- [C (CH3) 3] -N- (2-methylpropyl) aminocarbonyl, preferably C0- N (CH3) 2 or CO-N (C2H5) 2; di (C 1 -C 4 -alkyl) amino-C 1-4 alkyl-alkyl represents: C, -C 4 -alkyl substituted by di (C, -C 4 -alkyl) aminocarbonyl, as mentioned above, preferably CO-N (CH 3) 2 or CO- N (C2H5), is to ignore, for example, CH2-CO-N (CH3) 2, CH2-CO-N (C2Hs) 2, CH (CH3) -CO-N (CH3) 2 or CH (CH3) ) -CO-N (C2H5) 2, preferably CH2-CO- N (CH,) 2 or CH (CH3) -CO-N (CH,) 2; di (C, -C 4 -alkyl) phosphonyl represents: -PO (OCH 3) 2, -PO (OC 2 H 5) 2, N, N-dipropylphosphonyl, N, N-d - (1-methylethyl) phospho- & ^ S ^^ I ^^^^^^^^^^^^ g SK? tim fonilo, N-ethyl-N-methylphosphonyl, N-methyl-N-propylphosphonyl, N-methyl-N- (1-methylethyl) phosphonyl, N-butyl-N-methylphosphonoyl, N-methyl-N- (1-methylpropyl) -phosphonyl, N-methyl-N- (2-methylpropyl) -phosphonyl, N- (1,1-dimethylethyl) -N-methylphosphonyl, N-ethyl-N-propylphosphonyl, N-ethyl-N- (1-methylethyl) phosphonyl, N-butyl-N-ethylphosphonyl, N-ethyl-N- (1-methylpropyl) phosphonyl, N-ethyl-N- (2-methylpropyl) 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-propylphosphonyl, N- (1, 1-dimethylethyl) -N-propylphosphonyl, N-butyl-N- (1-methylethyl) phosphonyl, N- (1-methylethyl) -N- (1-methylpro-pyl) phosphonyl, N- (1-methylethyl) -N - (2-methylpropyl) phosphonyl, N- (1,1-dimethylethyl) -N- (1-methylethyl) phosphonyl, N-butyl-N- (1-methylpropyl) phosphonyl, 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 -P0 (0CH3) 2 or -PO (OC2H5) 2; di (C, -C4-alkyl) phosphonyl-C ^ Cj-alkyl represents: Cj-C, -alkyl substituted by di (C, -C4-alkyl) phosphonyl, as mentioned above, preferably -PO (OCH3) 2 or -PO (OC2H5) 2, ie, for example, CH2-PO (OCH,) 2, CH2-PO (OC2Hs) 2, CH (CH3) -PO (OCH3) 2 or CH (CH3) -PO (OC2Hs) 2; "" "^ mt) lilt2SÉÍt ---- ¿S *? - methyletenyl, 1-buten-l-yl, l-buten-2-yl, l-buten-3-yl, 2-buten-1-yl, 1-methyl-l-propen-l-yl, 2-methyl- l-propen-l-α, l-methyl-2-propen-l-yl, 2-methyl-2-propeny-l-yl, n-penten-1-yl, n-penten-2-yl, n -penten-3-yl, n-penten-4-yl, 1-methyl-1-buten-l-yl, 2-methyl-l-buten-l-yl, 3-methyl-l-buten-l-yl , l-methyl-2-buten-l-yl, 2-methyl-2-buten-l-yl, 3-methyl-2-buten-1-yl, l-methyl-3-buten-l-yl, 2 -methyl-3-buten-l-yl, 3-methyl-3-buten-l-yl, 1, l-dimethyl-2-propen-l-yl, 1,2-dimethyl-l-propen-1-yl , l, 2-dimethyl-2-propen-l-yl, l-ethyl-l-propen-2-yl, l-ethyl-2-propen-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, -methyl-1-penten-1-yl, 2-methyl-1-penten-1-yl, 3-methyl-1-penten-1-yl, 4-methyl-1-penten-1-yl, methyl-2-penten-l -yl, 2-methyl-2-penten-1-yl, 3-methyl-2-enten-1-yl, 4-methyl-2-penten-1-yl, l-methyl -3-penten-l-yl, 2-methyl-3-penten-l-yl, 3-methyl-3-penten-l-yl, 4-methyl-3-penten-l-yl, l-methyl-4 -penten-1-yl, 2-methyl-4 -penten-l-yl, 3-methyl-4-penten-l-yl, 4-methyl-4-penten-l-yl, 1, l-dimethyl-2-buten-l-yl, 1,1-dimethyl -3-buten-l-yl, 1,2-dimethyl-l-buten-l-yl, 1,2-dimethyl-2-buten-l-yl, l, 2-dimethyl-3-buten-l-yl , 1,3-dimethyl-1-buten-1-yl, 1,3-dimethyl-2-buten-1-yl, 1,3-dimethyl-3-buten-1-yl, 2,2-dimethyl-3 -buten-l-yl, 2,3-dimethyl-1-buten-1-yl, 2,3-dimethyl-2-buten-1-yl, 2,3-dimethyl-3-buten-1-yl, 3 , 3-dimethyl-1-buten-l-yl, 3, 3-dimethyl-2-buten-l-yl, 1-ethyl-l-buten-l- 1, 1, 2-trimethyl-2-propen-1-yl, l-et? Ll-met? L-2-propen-l-? Lo, l-ethyl-2-methyl-l-propen-l-yl or l-et? l-2-metll-2-propen-l-yl; C3-C6-haloalkenyl represents: C3-Ct-alchemyl, as mentioned above, which is partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, 2-chloroallyl, 3-chloroallyl, , 3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichloro-2-butenyl, 2-bromoalyl, 3-bromoalyl, 2,3-dibromoalyl, 3,3-dibromoalyl , 2,3,3-tribromoalyl or 2,3-dibromo-2-butenyl; cyano-C3-C6-alkenyl represents: for example, 2-cyanoal? lo, 3-cyanoalyl, 4-cyano-2-butenyl, 4-cyano-3-butenyl 5-cyano-4-pentenyl; C3-C6-alkynyl represents: 1-propin-1-yl, 2-propin-1-yl, n-but-1-yn-l-yl, n-but-l-yn-3-yl, n-but- l-in-4-yl, n-but-2 in-l-yl, n-pent-1-yn-l-yl, n-pent-l-in-3-yl, n-pent-l-yl -4-yl, n-pent-l-in-5-yl, n-pent-2-yn-l-yl, n-pent-2-yn-4-yl n-pent-2-yn-5-yl , 3-methyl-l-butin-3-yl, 3-methyl-l-butin-4-yl, n-hex-1-yn-l-yl, n-hex-l-in-3-yl, n- hex-l-? n-4-yl, n-hex-l-in-5-yl, n-hex-l-in-6-yl, n-hex-2-yn-l-yl, n-hex- 2-in-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-yl, n-hex-3-yl 2-yl, 3-methyl-l-pentin-l-yl, 3-methyl-pentin-3-yl, 3-methyl-l-pentan-4-yl, 3-methyl-l-pent ? n-5-? C3-C6-haloalkynyl represents: C3-C6-alkynyl, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, 1, 1-difluor-2-propin -l-ilo, 4-fluoro-2-butin-1-yl, 4-chloro-2-butin-1-yl, 1, 1-difluor-2-butin-1-yl S-fluoro-3-pentyl- 1-yl or 6-fluoro-4-hexin-1-yl ?; cyano-C3-C6-alkynyl represents: for example, 3-cyanopropargyl, 4-cyano-2-buten-l-yl, 5-cyano-3-pentin-1-yl and 6-cyano-4-hexin-l- ilo; C3-C4-alkenyloxy-C, -C4-alkyl represents: C, -C4-alkyl substituted by C, -C4-alkenyloxy, such as allyloxy, l-buten-3-yloxy, 1-buten-4-yloxy, 2- buten-l-iloxy, l-met? l-2-propenyloxy or 2-methyl-propenyloxy, ie, for example, allyloxymethyl, 2-allyloxymethyl or l-buten-4-yloxymethyl, especially 2-allyloxymethyl; C, -C4-alkynyloxy-C1-C4-alkyl represents: C, -C4-alkyl substituted by C3-C4-alkynyloxy such as propargyloxy, l-butyne-3-yloxy, l-butyne-4-yloxy, 2-butynyl- 1-yloxy, 1-methyl-2-propynyloxy or 2-methyl-2-propynyloxy, preferably propargyloxy, ie, for example, propargyloxymethyl or 2-propargyloxyethyl, espe- 32 -'-- "-" • - * »» - (C3-C4-alkenyloxy) imino-C, -C4-alkyl represents: Cj-C-alkyl substituted by (C3-C4-alkenyloxy) imino, such as allyloximino, 1-buten-3-yloximino, l-buten-4- iloximino, 2-buten-l-yloxim? no, l-methyl-2-propenyloximino or 2-methyl-2-propenyloximino, ie, for example, alkoxy-N = CH-CH2 or l-buten-4 -iloxy-N = CH, especially allyloxy-N = CH-CH2; C, -C 4 -alkenylthio-C, -C 4 -alkyl represents: C, -C 4 -alkyl substituted by C, -C 4 -alkenylthio such as allylthio, l-buten-3-ylthio, 1-buten-4-ylthio, 2- buten-l-ylthio, l-methyl-2-propethylthio or 2-methyl-2-propenylthio, ie, for example, allylthiomethyl, 2-allylthioethyl or l-buten-4-ylthiomethyl, especially 2- (allylthio) ethyl; C, -C4-alkynylthio-C1-C4-alkyl represents: C, -C4-alkyl substituted by C, -C4-alkynylthio, such as propargylthio, l-butin-3-ylthio, l-butin-4-ylthio, 2- butin-l-ylthio, l-methyl-2-propinylthio or 2-methyl-2-propinylthio, preferably propargylthio, ie, for example, propargylthiomethyl or 2-propargthylthio, especially 2- (propargthylthio) ethyl; C3-C4-alkenylsulfinyl-C, -C4-alkyl represents: C, -C4-alkyl substituted by C3-C4-alkenylsulfinyl, such as allylsulfinyl, 1-buten-3-ylsulfinyl, l-buten-4-ylsulfinyl, 2-buten -l- ,,,, 2-allylsulfinylethyl or l-buten-4-ylsulfinylmethyl, especially 2- (allylsulfinyl) ethyl; C, -C4-alkynylsulfinyl-C, -C4-alkyl represents: C1-C, -alkyl substituted by C, -C4-alkynylsulfinyl, such as propargylsulfinyl, l-butyne-3-ylsulfinyl, l-butyne-4-ylsulfinyl, -butin-1-ylsulfinyl, l-methyl-2-propynylsulfinyl or 2-methyl-2-propynylsulfinyl, preferably propargyl-sulfinyl, ie, for example, propargyl-sulfinylmethyl or 2-propargyl-sulfonyl-ethyl, especially 2- (propargyl-sulfinyl) -ethyl; C3-C4-alkenylsulfonyl-C1-C4-alkyl represents: C1-C4-alkyl substituted by C, -C4-alkenylsulfonyl, such as allylsulfonyl, 1-buten-3-ylsulfonyl, l-buten-4-ylsulfonyl, 2- buten-l-ylsulfonyl, l-methyl-2-propenylsulfonyl or 2-methyl-2-propenylsulfonyl, ie, for example, allylsulfonylmethyl, 2-allylsulfonylethyl or l-buten-4-ylsulfonylmethyl, especially 2- (allylsulfonyl) ethyl; Cj-Cj-alkynylsulfonyl-Cj-C-alkyl represents: C, -C4-alkyl substituted by C3-C4-alkynylsulfonyl, such as propargyl sulfonyl, l-butyn-3-ylsulfonyl, l-butyn-4-ylsulfonyl, -butyn-l-ylsulfonyl, l-methyl-2-propynylsulfonyl or 2-methyl-2-propynylsulfonyl, preferably propargyl sulfonyl, ie, for example, propargyl sulfonylmethyl or 2-propargyl sulphonyl 3. 4 i • '- i ifH-r if C3-CB-cycloalkyl represents: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl; C3-C, cycloalkyl-C ^ Cs-alkyl represents: for example, cyclo-propylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl-methyl, cycloheptylmethyl, cyclooctylmethyl, 2- (cyclo-propiDethyl, 2- (cyclobutyl) ethyl, 2- ( cyclopentyl) ethyl, 2- (cyclohexyl) ethyl, 2- (cycloheptyl) ethyl, 2- (cyclooctyl) ethyl, 3- (cyclopropyl) propyl, 3- (cyclobutyl) propyl, 3- (cyclopentyl) propyl, 3- (cyclohexyl) propyl , 3- (cycloheptyl) propyl, 3- (cyclooctyl) propyl, 4- (cyclopropyl) butyl, 4- (cyclobutybutyl, 4- (cyclopentyl) butyl, 4- (cyclohexyl) butyl, 4- (cycloheptyl) butyl, 4- (cyclooctyl) butyl, 5- (cyclopropyl), 5- (cyclobutyl) pentyl, 5- (cyclopentyl) pentyl, 5- (cyclohexyl) pentyl, 5- (cycloheptyl) pentyl, 5- (cyclooctyl) pentyl, - (cyclopropyl) hexyl, 6- (cyclobutyl) hexyl, 6- (cyclopentyl) hexyl, 6- (cyclohexyl) hexyl, 6- (cycloheptyl) hexyl, 6- (cyclooctyl) hexyl ?; C3-Cβ-cycloalkyl containing a carbonyl or thiocarbonyl ring linkage represents, for example, cyclobutanon-2-yl, cyclobutanon-3-yl, cyclopentanon-2-yl, cyclopentanon-3-yl, cyclohexanon-2-yl, cyclohexanon-4-yl, cycloheptanon-2-yl, cyclooctanon-2-yl, cyclobutanethione-2-yl, cyclobutane-thion-3-yl, cyclopentanot-on-2-yl, c-clopentanothione-3-yl, tanon-2-yl or cyclohexanon-2-yl ?; Cj-Cβ-cycloalkyl-Cj-C ^ -alkyl, which contains a carbonyl ring or thiocarbonyl ring represents: for example, cyclobutanon-2-yl-methyl, cyclobutanon-3-yl-methyl, cyclopenta-non-2 -yl-methyl, cyclopentanon-3-yl-methyl, cyclohexanon-2-yl-methyl, cyclohexanon-4-y-methyl, cycloheptanon-2-yl-methyl, cyclooctanon-2-yl-methyl, cyclobutanethion-2 -yl-methyl, cyclo-butanethion-3-yl-methyl, cyclopentanothion-2-yl-methyl, cyclo-pentanotion-3-yl-methyl, cyclohexanothion-2-yl-methyl, cyclohexanothion-4-yl-methyl, cycloheptanothion-2-yl-methyl, cycloocta-notion-2-yl-methyl, 1- (cyclobutanon-2-yl) ethyl, 1- (cyclobuta-non-3-yl) ) ethyl, 1- (cyclopentanon-2-yl) ethyl, 1- (cyclopentanon-3-yl) ethyl, 1- (cyclohexanon-2-yl) ethyl, 1- (cyclohexanon-4-yl) ethyl, 1- ( cycloheptanon-2-? l) ethyl, 1- (c? cloc-anon-2-yl) ethyl, 1- (cyclobutanethion-2-yl) ethyl, 1- (cyclobutanethion-3-yl) ethyl, 1- (cyclo? entanothion-2-? l) ethyl, 1- (cyclopentanothion-3-yl) ethyl, 1- (cyclohexanothion-2-yl) ethyl, 1- (cyclohexanothion-4-yl) ethyl, 1- (cycloheptanothion-2-yl) ) ethyl, 1- (cyclooctane-thioth-2-yl) ethyl, 2- (cyclobutanon-2-yl) ethyl, 2- (cyclobutanon-3-yl) ethyl, 2- (cyclopentanon-2-yl) ethyl, 2 - (cyclopentanon-3-yl) ethyl, 2- (cyclohexanon-2-yl) ethyl, 2- (cyclohexanon-4-yl) ethyl, 2- (cycloheptanon-2-yl) ethyl, 2- (cyclooctane-2) il) ethyl, 2-cyclobutanethion-2-yl) ethyl, 2- (cyclobutaneth-3-) 4-yl) ethyl, 2- (cycloheptanothion-2-yl) ethyl, 2- (cyclooctane-2-yl) ethyl, 3- (cyclobutanon-2-yl) propyl, 3- (cyclobutanon-3-yl) propyl, 3- (cyclopentanon-2-yl) propyl, 3- (cyclopentanon-3-yl) propyl, 3- (cyclohexanon-2-yl) propyl, 3- cyclohexanon-4-yl) propyl, 3- (cycloheptanon- 2-yl) propyl, 3- (cyclooctanon-2-yl) propyl, 3- (cyclobutanethion-2-yl) propyl, 3- (cyclobutanethion-3-yl) propyl, 3- (cyclopentanothione-2-ylpropyl) 3- (cyclopentanothion-3-yl) propyl, 3- (cyclohexanedith-2-yl) propyl, 3- (cyclohexanothion-4-yl) propyl, 3- (cycloheptanothion-2-yl) propyl, 3- (cyclooctanotion) -2-yl) propyl, 4- (cyclobutanon-2-yl) butyl, 4- (cyclobutanon-3-yl) butyl, 4- (cyclopentanon-2-yl) butyl, 4- (cyclopentanon-3-yl) butyl 4- (cyclohexanon-2-yl) butyl, 4- (cyclohexanon-4-yl) butyl, 4- (cycloheptanon-2-yl) butyl, 4- (cyclooctanon-2-yl) utilo, 4- (cyclobutanethion-) 2-yl) butyl, 4- (cyclobutanethion-3-yl) butyl, 4- (cyclopentanothion-2-yl) butyl, 4-cyclopentanothion-3-yl) butyl, 4- (c iclohexanothion-2-yl) butyl, 4- (cyclohexanothion-4-ylbutyl, 4- (cycloheptanothion-2-yl) butyl or 4- (cyclooctanethion-2-yl) butyl; C3-C, -cycloalkyloxy-C, -C4-alkyl represents: Cyclopropyloxymethyl, 1-cyclopropyloxyethyl, 2-cyclopropyloxyethyl, 1-cyclopropyloxy-1-propyl, 2-cyclopropyloxy-1-propyl, 3-cyclopropyloxy-1-propyl , 1-cyclopropyloxy-l-butyl, 2- ^ tf ^ gga ^ g ^^^^^^ Cyclopropyloxy-2-butyl, 3-cyclopropyloxy-2-butyl, 3-cyclopropyloxy-2-butyl, 4-cyclopropyloxy-2-butyl, 1- (cyclopropyloxymethyl) -1-ethyl, 1- (cyclopropyloxymethyl) -1- (CH,) -1-ethyl, 1- (cyclopropyloxymethyloxy) -1-propyl, cyclobutyloxy-methyl, 1-cyclobutyloxy-ethyl, 2-cyclobutyloxy-ethyl, cyclobu-1-yloxy-1-propyl, 2-cyclobutyloxy-1-propyl, cyclobutyloxy-1-propyl, 1-cyclobutyloxy-1-butyl, cyclobutyloxy-1-butyl, 3-cyclobutyloxy-1-butyl, cyclobuoyloxy-1-butyl, 1-cyclobutyloxy-2-butyl, cyclobutyloxy-2-butyl, -cyclobutyloxy-2-butyl, cyclobutyloxy-2-butyl, 4-cyclobutyloxy-2-butyl, (cyclobutyloxymethyl) -1-ethyl, 1- (cyclobutyloxymethyl) -1- (CH,) -1-ethyl, 1- (cyclobutyloxymethyl) ) -1-propyl, cyclopentyloxymethyl, 1-cyclopentyloxy-ethyl, 2-cyclopentyloxy-ethyl, 1-cyclopentyloxy-1-propyl, 2-cyclopentyloxy-1-propyl, 3-cyclopentyloxy-1-propyl, 1-cyclopentyloxy-1- butyl, 2-cyclopen-yloxy-1-butyl, 3-cyclopentyloxy-l-butyl, 4-cyclopentyloxy-1-butyl, l-cyclopentyloxy-2-butyl, 2-c iclopentyloxy-2-buyl, 3-cyclopentyloxy-2-butyl, 3-cyclopentyloxy-2-butyl, 4-cyclopentyloxy-2-butyl, 1- (cyclopentyloxymethyl) -1-ethyl, 1- (cyclopentyloxymethyl) -1- ( CH,) -1-ethyl, 1- (cyclopentyloxymethyl) -1-propyl, cyclohexyloxymethyl, 1-cyclohexyloxy-ethyl, 2-cyclohexyloxy-ethyl, 1-cyclohexyloxy-1-propyl, 2-cyclohexyloxy-1-propyl, 3- cyclohexyloxy-1-butyl, 1-cyclohexyloxy-2-butyl, 2-cyclohexyloxy-2-butyl, 3-cyclohexyloxy-2-butyl, 3-cyclohexyloxy-2-butyl, 4-cyclohexyloxy-2-butyl, 1- (cyclohexyloxymethyl) ) -1-ethyl, 1- (cyclohexyloxymethyl) -1- (CH,) -1-ethyl, 1- (cyclohexyloxymethyl) -1-propyl, cycloheptyloxymethyl, 1-cycloheptyloxy-ethyl, 2-cycloheptyloxy-ethyl, 1-cycloheptyloxy -1-propyl, 2-cycloheptyloxy-1-propyl, 3-cycloheptyloxy-1-propyl, 1-cycloheptyloxy-1-butyl, 2-cycloheptyloxy-1-butyl, 3-cycloheptyloxy-1-butyl, 4-cycloheptyloxy-1 -butyl, l-cycloheptyloxy-2-butyl, 2-cycloheptyloxy-2-butyl, 3-cycloheptyloxy-2-butyl, 3-cycloheptyloxy-2-butyl, 4-cycloheptyloxy-2-butyl, 1- (cycloheptyloxymethyl) -1 -ethyl, 1- (cycloheptyloxymethyl) -1- (CH,) -1-ethyl, 1- (cycloheptyloxymethyl) -1-propyl, cyclooctyloxymethyl, 1-cyclooctyloxy-ethyl, 2-cyclooctyloxy-ethyl, 1-cyclooctyloxy- 1-propyl, 2-cyclooctyloxy-1-propyl, 3-cyclooctyloxy-1-propyl, 1-cyclooctyloxy-1-butyl, 2-cyclooctyloxy-1-butyl, 3-cyclooctyloxy butyl, 4-cyclooctyloxy-1-butyl, 1-cyclooctyloxy-2-butyl, 2-cyclooxyloxy-2-butyl, 3-cyclooctyloxy-2-butyl, 3-cyclooctyloxy-2-butyl, 4-cyclooctyloxy-2 butyl, 1- (cyclooctyloxymethyl) -1-ethyl, 1- (cyclooctyloxymethyl) -1- (CH,) -1-ethyl or 1 (cyclooctyloxymethyl) -1-propyl, especially C, -Cβ-cycloalkoxymethyl or 2- (C3 -C6-cycloalkoxy) ethyl. saturated heterocycles, partially or totally unsaturated, as well as aromatics, with one to three heteroatoms, chosen from a group consisting of - from one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms.

Examples of saturated heterocycles which can contain is-Labón ring carbonyl or thiocarbonyl are: oxiranyl, thiiranyl, 1-aziridinyl, 2-aziridinyl, diaziridín-l-yl, diaziridin-3-yl, 2-oxetanyl, 3-oxetanyl , 2-thietanyl, 3-thietanyl, 1-azetidinyl, 2-azetidinyl, 3-azetidinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 3-tetrahydrothiophenyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, , 3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1 , 3-oxazolidin-2-yl, 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, l , 2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 1-pyrrolidinyl, 2-pyrrolidinyl, 5-pyrrolidinyl, 1-tetrahydropyrazolyl, 3-tetrahydropyrazolyl, 4-tetrah? Dropira-zolyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydro-pyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyr anyl, 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3- oxatian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathiane-3-yl, 2-morpholinyl, 3-morpholinyl, 4-morpholinyl, 1-hexahydropyridazinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 1-hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 1-piperazinyl, 2-piperazinyl, 3-piperazinyl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1, 3, yl 5-triazin-2-2-oxepanyl, 3-oxepanyl, 4-oxepanyl, 2-thiepanyl, 3-thiepanyl, 4-thiepanyl, 1, 3-dioxepan-2-yl-1, 3-dioxepan-4- ilo, 1,3-dioxepan-5-yl, 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7 ilo, 1-hexahydroazepinyl, 2-hexahydroazepinyl, 3-hexahydroazepinyl, 4-hexahydroazepinyl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahi-dro-1, 3- diazepin-4-yl, hexahydro-1, -diazepin-1-yl and hexahydrs-1,4-diazepin-2-yl. Examples of unsaturated heterocycles which may contain a link or thiocarbonyl ring carbonyl are: 2-dihydrofuranyl, 1, 2-oxazolin-yl-2-oxazolin 5-3-yl, 1, 1,3-oxazolin-2- ilo. Among the aromatic heterocycles are preferably 5 and 6-membered, ie, for example, furyl as 2-furyl and 3-furyl, thienyl as 2-thienyl and 3-thienyl, pyrrolyl as 2-pyrrolyl and 3- pyrrolyl, isoxazolyl 3-isoxazolyl and 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazole? I, pyrazolyl-pyrazole as 3? I, 4- thiazolyl, imidazolyl such as 2-midazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2,4-oxadiazol-3-yl, 1, 2, 4-oxadiazol-5-yl and 1,3,4-oxadiazole-2 -yl, thiadiazolyl such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-2-yl, triazolyl as 1,2,4-triazole -1-yl, 1, 2,4-triazol-3-yl and l, 2,4-triazol-4-yl, pyridinyl as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl as 3-pyridazinyl and 4- pyridazinyl, pyrimidinyl 2-pyrimidinyl and 4-pyrimidinyl and 5-pyrimidinyl, 2-pirazimlo addition, 1, 3, 5-triazin-2-yl and 1, 2,4-triazin-3-yl, especially pyridyl, pyrimidyl, furanyl and thienyl. All phenyl, carbocyclic and heterocyclic rings are preferably unsubstituted or carry a substituent.

In view of the application of the substituted (4-bromopyrazol-3-yl) benzazoles I as herbicides or degenation-tes / defoliants are preferably those compounds in which the variables have the following meanings, alone or in combination: R 1 C, -C 4 -alkyl, especially methyl; R! C, -C4-haldgenoalquilo, C, -C4-haloalkoxy, or C, -C, - alkylsulfonyl, especially C, -C4-halogenoalkoxy or C, - C4-alkylsulphonyl, particularly preferably difluormeto- Rs cyano, halogen, or trifluoromethyl, especially halogen, especially preferably chlorine; 5 To a group -N = C (XR5) -o- or -N = C (XR8) -S- bonded to aaa through oxygen or sulfur, especially a group -N = C (XRβ) -0- bound aaa through oxygen; And 10 X a chemical bond, oxygen, sulfur, -NH or -N (R7); R6, R7, independently from each other, C, -C3-alkyl, C1-C3-haloalkyl, cyano-C, -C4-alkyl, hydroxy-C ^ C.-alkyl, C3-C, -alkenyl , C, -C6-alkynyl, C, -C4-alkoxy-C, -C4-alkyl, C, -C4-alkylthio-C1-C4-alkyl, C, -C4-alkylsulfonyl-C ^ C, - alkyl, (C, -C4-alkoxy) carbonyl, C, -C4-alkyl, di (C1-C4-alkyl) aminocarbonyl-C1-C4-alkyl, C3-C, -cycloalkyl, C3-CB-cycloalkyl-C, -C 4 -alkyl, phenyl or phenyl-C, -C 4 -alkyl; 2o as long as X is a chemical bond, oxygen, sulfur, -NH- or -N (R '), then Rs can also mean (C, -C 4 -alkyl) carbonyl or C, -C 4 -alkylsulfonyl; as long as X is a chemical bond, then R6 can also mean hydrogen, cyano, amino, halogen or -CH = CH-R "; R, R ca to a special menu, - f-a qu? or,? -, - 4-alkyl, C, -C6-alkenyl, C3-C6-alkylene or (C, -C4-alkoxyl) carboml-C, -C4-alkyl, as long as X is a chemical bond, Rs can also mean especially hydrogen or -CH-CH-R; R ° (C, -C 4 -alkox?) Carbon? Lo.

Of very particular preference are the substituted (4-bromop? Razol-3-dibenzazoles of the formula la (U I with R1 = methyl, R '= difluoromethoxy, R' = hydrogen, Rs = chloro, Z = -N = C (XRI ) -S- bonded aaa through the sulfur), especially the compounds that are presented in the following table 1: TABLE 1 • "*" - - - • * --- ma ^ &aM gtij ^^^ y. 52 g ^^^ j ^ 53 54 ÜÉ'lfl T? -T iri-BT ' em s os - romop? razo - -? Enzazo is their formulas from Ib to It and from AI to IT are of special preference, particularly the compounds Ib.001 to Ib.393, which differ from the corresponding compounds la.001 to la.393, simply because R4 represents chlorine: the compounds Ic.001 to Ic.393, which differ from the corresponding compounds la.001 to la.393, simply because R 'represents fluorine: the compounds Id.001 to Id.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents trifluoromethyl: XHS the compounds le.001 to le 393, which differ from the corresponding compounds 001 to la.393, simply because R2 represents trifluoromethyl and R * represents chloro: the compounds If.001 to If.393, which differ from the corresponding compounds la.001 to la.393, simply because R1 represents tpfluoromethyl and R * represents fluorine: the compounds Ig.001 to Ig.393, which differ from the corresponding compounds la.001 to la.393, simply because R! represents methylsulfomide: t ...-. »--........, -. ^ - the compounds Ih.001 to Ih.393, which differ from the corresponding compounds la.001 to la.393, simply because R represents methylsulfonyl and R * represents chloro: the compounds Ij.001 to Ij.393, which differ from the corresponding compounds la.001 to la.393, simply because RJ represents methylsulfonyl and R * represents fluorine: Compounds I .001 to I.393, which differ from the corresponding compounds la.001 to la.393, simply ^ Nm ^^^^^^^^ n ^^ because it means a group - = - - that is uni or by means of oxygen a Br. T? T-Hl-2 Cl - y- (u < -H, ti., Or Y. the compounds Im.001 to Im.393, which differ from the corresponding compounds 001 to the 393, simply because R 'represents chlorine and Z means a group -N'CIXR'l-O- which is bound by means of oxygen aa: the compounds In.001 to In.393, which differ from the corresponding compounds la.001 to la.393, simply because R * represents fluorine and Z means a group -N = C (XR ") - 0- which is linked by means of oxygen aa: 59 nlllY lll irai WlHIlliíllilí ni i ni -l? ÜÉ * i ^ V * - * -? l m because R3 represents trifluor ethyl and Z means a group -N = C (XR6) -O- which is linked by means of oxygen to a: Br, CF, Cl V, -, N O Y the compounds Ip.001 to Ip.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents triflusr ethyl and R4 represents chlorine and Z means a group -N = C (XRβ) -O- which is united by means of oxygen aa: the compounds Iq.001 to Iq.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents tpfluoromethyl and R represents fluorine and Z means a group -N = C (XR6) -O- which is united by means of oxygen aa: the compounds Ir.001 to Ir.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents methylsulfsyl and Z means a group -N = C (XRs) -0- which is bound by of oxygen aa: the compounds Is.001 to Is.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents methylsulfonyl and R4 represents chlorine and Z means a group -N = C (XRs) -0- which is united by means of oxygen aa: . . , because R 2 represents methylsulfonyl and R 4 represents fluorine and Z means a group -N = C (XR 6) -O- which is linked by means of oxygen to a: compounds IA.001 to IA.393, which differ from the corresponding compounds la.001 to la.393, simply because the group -N = C (XRβ) -S- is linked by means of nitrogen a to: the compounds IB.001 to IB. 93, which differ from the corresponding compounds la.001 through la. 93, simply because R * represents chlorine and the group -N = C (XR6) -S- is linked via nitrogen to a: the compounds IC.001 to IC.393, which differ from the corresponding compounds 001 to the 393, simply because R * represents fluorine and the group -N = C (XRS) -S- is bound by nitrogen aa : compounds ID.001 to ID 393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents tpfluoromethyl and the group -N = C (XRS) -S- is linked via nitrogen to a: 63 ^^^^ * ^ , because R2 represents trifluoromethyl and R * represents chlorine and the group -N < = C (XR6) S- is bound by nitrogen to a the compounds IP 001 to IF 393, which differ from the corresponding compounds 001 to 393, simply because R2 represents tpfluoromethyl and R * represents fluorine and the group -N = C (XRd) -S- is linked by means of nitrogen aa the compounds IG.001 to IG 393, which differ from the corresponding compounds 001 to 393, simply because R2 represents methylsulfonyl and the group -N = C (XR6) -S- is linked via nitrogen to a the compounds IH 001 to IH 393, which differ from the corresponding compounds 001 to 393, simply because R2 represents methylsulfonyl and R * represents chlorine and the group -N = C (XRS) -S- is linked by means of nitrogen aa the compounds IJ 001 to IJ 393, which differ from the corresponding compounds 001 to 393, simply because R2 represents methylsulfonyl and R 'represents fluorine and the group -N = C (XR6) -S- is linked by means of nitrogen aa CHj . . , because Z means a group -N = C (XR6) -0- which is linked via nitrogen to a: the compounds IM.001 to I.393, which differ from the corresponding compounds la.001 to la.393, simply because R 'represents chlorine and Z means a group -N = C (XRs) -0- which is linked by mean nitrogen aa: the compounds IN.001 to IN.393, which differ from the corresponding compounds la.001 to la.393, simply because R 'represents fluorine and Z means a group -N = C (XR ") -O-which is linked by means of nitrogen aa: 66 rM ai the compounds 10 001 to 10 393, which differ from the corresponding compounds 001 to 393, simply because R2 represents trifluoromethyl and Z means a group -N = C (XR6) -0- which is linked by means of nitrogen to a the compounds IP 001 to IP 393, which differ from the corresponding compounds 001 to 393, simply because R2 represents trifluoromethyl and R 'represents chlorine and Z means a group -N = C (XR6) -0- which is linked by mean nitrogen aa . . , because R2 represents trifluoromethyl and R * represents fluorine and Z means a group -N = C (XR6) -0- which is linked via nitrogen to a: the compounds IR.001 to IR.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents methylsulfonyl and Z means a group -N = C (XRs) -0- which is bound by of nitrogen aa: the compounds IS.001 to IS.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents methylsulfonyl and R * represents chlorine and Z means a group -N = C (XR6) -0- which is united by means of compounds IT.001 to IT.393, which differ from the corresponding compounds la.001 to la.393, simply because R2 represents methylsulfonyl and R * represents fluorine and Z means a group -N = C (XR6) -0- which is bound by nitrogen aa: The substituted (4-bromop? Razol-3-? L) benzazoles of formula I are obtainable in various ways, especially by means of one of the following processes A) Transformation of an aminophenylpyrazole of formula Illa or lllb with a halogen and thiocyanate of ammonium or with an alkali or alkaline-earth metal thiocyanate : ?? b MA = alkali metal ion or 1/2 alkaline earth metal ion A halogen is preferably chlorine or bromine; among the alkali metal / alkaline earth metal thiocyanates, sodium thiocyanate is preferred. Generally one works in an inert solvent / diluent, for example, in a hydrocarbon such as toluene and hexane, in a halogenated hydrocarbon such as dichloromethane, an ether such as tetrahydrofuran, an alcohol such as ethanol, in a carboxylic acid such as acetic acid or in an aprotic solvent such as dimethylformamide, acetonitrile and dimethisulfoxide. The temperature of the reaction is usually between the melting point and the boiling point of the reaction mixture, preferably between 0 and 150 ° C. In order to achieve the highest possible yield of the desired product, the halogen and ammonium thiocyanate or, where appropriate, alkali metal / alkaline earth metal thiocyanate, in an approximately equimolar or excess amount, up to 5 times molar, are used. the amount of Illa or Illb. A variant of the process consists in first converting the aminophenylpyrazole Illa or Illb with ammonium thiocyanate or a ? - ^ - ^ ar- Ml l l '' - "T ^" - "" ifr - * »* te ^ kM __ ^ fcttM ^ ttWBM'-Ífc thiourea IVa or IVb and then transforming IVa or IVb into I with Z = -N = C (XRÍ) -S, by treatment with a halogen. B) Diazotization of an aminophenylpyrazole of formula Illa or Illb, transformation of the respective diazonium salt into an azidophenylpyrazole of formula Va or Vb and the transformation thereof either Bl) with a carboxylic acid, or B.2) first with a sulfonic acid (to obtain Vía or VIb), hydrolysis of the sulfonate formed to obtain an aminophenol Vlla or Vllb, and its transformation into I: pt r - • ° -a - - "" - alkaline earth I (Z - -N = C (XR °) -0- (Z - -N ^ fXK ^ -O- unldo n O by means of oxygen) bound 11 O by means of the nltr? Grno) To carry out diazotization, the indications made for procedure C) are valid. The transformation in the Va / Vb arylazides is preferably carried out by transformation of Illa / IIIb with an alkali metal or alkaline earth metal azide, such as sodium azide or by transformation with trimethylsilyl azide. In the transformation enunciated in B.l), with a carboxylic acid dimethylformamide and acetonitrile, a hydrocarbon such as toluene and hexane, a halogenated hydrocarbon such as dichloromethane, or without a solvent, in an excess of carboxylic acid R'-COOH. In the latter case it may be useful to add a mineral acid such as phosphoric acid. The transformation is preferably carried out at elevated temperature, for example, at the boiling temperature of the reaction mixture. For the first mentioned transformation in B.2), of Va / Vb with a sulphonic acid R ° -S0H (where R ° represents C, -C &-alkyl or C 1 -C 4 -haloalkyl, preferably methyl or trifluoromethyl) , the indications made above for the transformation of Va / Vb with Rs-CO0H are valid. The subsequent hydrolysis of the sulfonates Vla / VIb is preferably effected by transformation with an aqueous base such as sodium hydroxide solution and potassium hydroxide solution., where, if desired, a solvent can be added, for example, an ether such as dioxane and tetrahydrofluoride, or an alcohol such as methanol and ethanol. The final transformation to obtain I is known per se and can be carried out in many different ways. For this we refer to the indications in Houben-Weyl, "Methoden der Organischen Chemie ", Editorial Georg Thieme, Stuttgart, volume E8a 1993, p. 1032 and next. The azidophenylpyrazoles of formulas Va and Vb are new.

O Diazotization of (substituted 4-bromopyrazol-3-ylbenzazoles of formula I, in which XRS represents amino, and subsequent transformation of the diazonium salt into compounds I with XRS = cyano or halogen (for the Sandmeyer reaction compare, for example , with Houben-Weyl, "Methoden der Organische Chemie", Georg Thieme Publishing House, Stuttgart, volume 5/4, 4 * 1960 edition, page 438 ff.) en-Wey, "Met or en er Organ sc en em e", History Georg Thieme, Stuttgart, vol. Eli 1984, p. 43 and 176), XR6 = for example, -CH, -CH (halogen) -R1, -CH = CH-R ", CH = C (halogen) -Rß. {In general, these are products of an arylation. by Meer ein, for example, compare with CS Rondestredt, Org React 11, 189 (1960) and HP Doyle et al., J. Org. Chem. 42, 2431 (1977).

? (- »« «MH ,, D1" °)? V ». L (-XKs = zBCN, Htlo« A.-SR '. -CHyCH (Il «logcno) -R <, CH = C1I-R \ -CH-CIHalogenoj-R ') In general, the diazonium salt is obtained in a manner known per se by transformation of I with -XR6 = amino in an aqueous acid solution, for example in hydrochloric acid, hydrobromic acid or sulfuric acid, with a nitrite such as sodium nitrite and potassium nitrite. But there is also the possibility of working without water, for example, in glacial acetic acid containing hydrogen chloride or not, in absolute alcohol, in dioxane or in tetrahydrofuran, in acetonitrile or in acetone and treating the starting compound here (I). with -XRS = NHj) with a nitrous acid ester such as terbutyl nitrite and isopentyl nitrite. The transformation of the diazonium salt thus obtained into the corresponding compound I with -XR6 = cyano, chloro, bromo or iodo is effected with special preference by means of the treatment with copper (I), or with an alkali metal salt solution. Compounds I with ~ X- = sulfur are usually obtained by transformation of the diazonium salt with a dialkyl disulfide such as dimethyl disulfide and diethyl disulfide, or, for example, with diallyl disulfide or dibenzyl disulfide. In the arylation of Meer ein it is usually the transformation of the diazonium salts with alkenes (here H2C = CH-Rβ) or alkynes (here HC = C-RS). The alkene or alkyne preferably here r and is used in excess, up to about 3000 mol%, relative to the amount of diazonium salt. The transformations of the diazonium salt, described above, can be carried out, for example, in water, in aqueous hydrochloric acid or aqueous hydrobromic acid, in a ketone such as acetone, diethyl ketone and methyl ethyl ketone, in a nitrile such as acetonitrile, in an ether such as dioxane and tetrahydrofuran or in an alcohol such as methanol and ethanol. While not otherwise indicated for individual transformations, the reaction temperatures are usually between (-30) and + 50 ° C. Preferably all reaction participants are added in approximately stoichiometric amounts, however an excess of one or another component, up to about 3000% of 25 mol may also be advantageous. D) Oxidation of a substituted (4-bromopyrazol-3-yl) benzazole I, "Methsden der Or ^ &nischen Chemie", Editorial Georg Thie, Stuttgart, Volume E 11/1, 1985, pp. 702 ff., Volume IX, 4"edition, 1955, page 211): I. { X = S } oxidant ® I. { X = SO } Suitable oxidants are, for example, hydrogen peroxide, organic peroxides, such as acetic acid peroxide, trifluoroacetic acid peroxide, m-chloroperbenzoic acid, tert-butyl hydroperoxide and tert-butyl hydrochloride, as well as inorganic compounds such as sodium metaiodate, acid chromic and nitric acid.

Usually it works, according to the oxidant, in an organic acid such as acetic acid and trichloroacetic acid, in a chlorinated hydrocarbon such as methylene chloride, chloroform and 1,2-dichloroethane, in an aromatic hydrocarbon such as benzene, chlorobenzene or in a protic solvent such as methanol and ethanol. Mixtures of the stated solvents also come into consideration. The reaction temperature in general is between (-30) ° C and the boiling temperature of the respective reaction mixture, where the lower temperature range is usually preferred. Conveniently it is used in starting compound and the oxydant in approximately stoichiometric ratio, however one or the other component can be used in excess.

U | & £ with X = -SOj- in a manner known per se (compare, for example, with Houben-Weyl, "Methoden der Organischen Cheme", Georg Thieme, Stuttgart, volume E 11/2, 1985, p. 1132 and next. and Volume IX, 4 * edition, 1955, p. 222 ff. ): I. { X = S, SO} oxidant I { X = So Suitable oxidants are, for example, hydrogen peroxide, organic peroxides such as acetic acid peroxide, trifluoroacetic acid peroxide and m-chloroperbenzoic acid, as well as inorganic oxidants such as potassium permanganate. The presence of a catalyst, for example, tungstate, can have a boosting effect on the course of the reaction. Generally the transformation is carried out in an inert solvent, for which they are usable, according to the oxidant, for example, organic acids such as acetic acid and propionic acid, chlorinated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethane, hydrocarbons. aromatics or aromatic halogenated hydrocarbons such as benzene, chlorobenzene and toluene, or water. Mixtures of the stated solvents also come into consideration.

Normally, work is carried out at (-30) ° C up to the ebu-liter temperature of the respective reaction mixture, preferably at 10 ° C up to the boiling temperature. 78 »**« - chemistry To optimize the transformation of the starting compound, however, an excess of oxidant may be advisable. F) Transformation of a substituted (4-bromopyrazol-3-yl) benzazole I, in which the group -XR6 represents chloro, bromo, alkylsulfonyl or halogenoalkylsulfonyl, in the presence of a base, with an alcohol, mercaptan, an amine or a CH-acid compound.

V I H Rby R °, independently of each other, represent cyano or (C, -C, -alkoxy) carbonyl. Suitably, the transformation is carried out in an inert solvent, for example, in an ether such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, a ketone such as acetone, diethyl ketone, ethyl methyl ketone and cyclohexanone, a dipolar solvent aprotic such as acetonitrile, dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, a protic solvent such as methanol and ethanol, an aromatic hydrocarbon, if desired, halogenated, such as benzene, chlorobenzene and 1,2-dichlorobenzene, a heteroaromatic solvent such as pyridine and quinoline or a mixture of such solvents. Preference is given to tetrahydrofuran, acetone, diethyl ketone and dimethylformamide. of alkali and alkaline-ferrous metals, aliphatic tertiary amines such as triethylamine, N-methylmorpholine and N-ethyl-N, N-diisopropylamine, bi and tricyclic amines such as diazabicycloundecane (DBU) and diazabicyclooctane (DABCO), or nitrogenous aromatic bases such as pyridine, 4-dimethylaminopyridine and quinoline. Combinations of various bases are also considered. Bases of preference are sodium hydride, sodium hydroxide, sodium carbonate, potassium carbonate, sodium methylate, sodium ethylate and potassium r-butylate. The amines H¡NR6 or HN (R6) R7 can be participants of the reaction and at the same time serve as bases, in which case the amine must be present in an excess at least double with respect to the amount of starting compound I Of course a greater excess of amine, up to about 10 times molar, is also possible with respect to the amount of I with -XRS = Cl, Br, -S02-alkyl or -S03- halogenoalkyl. The starting compounds are usually used in approximately stoichiometric amounts, but an excess of one or the other component can also be advantageous in view of the conduct of the process or of the most complete possible conversion of the starting compound I. { -XR6 = Cl, Br, -SOj-alkyl, -S02- halogenoalkyl). The molar ratio of alcohol, mercaptan, amine or CH-acidic compound (VIII) to the base in general amounts to 1: 1 80 JÜIIIÉ »- *" '"- -" - ~~ it is usually between 0.1 and 5.0 moles / 1. The transformation can be carried out at temperatures of 0 ° C up to the reflux temperature of the respective reaction mixture. G) Transformation of a substituted (4-bromop? Razol-3?) Benzazole I, in which -XR6 represents halogen, with a compound of (Cj-C3-alkyugpard: Here Hal represents chloride or bromide. Generally one works in an inert solvent / diluent, for example, a hydrocarbon such as hexane and toluene, or an ether such as diethyl ether, tetrahydrofuran and dioxane. If desired, there can be added a transition metal catalyst in amounts of 0.0001 to 10 mol%. For this, for example, nickel and palladium catalysts, such as nickel dichloride, bis (tp-phenylphosphine) nickel dichloride, [bis- (1, 2-diphenylphosphine) ethane] nickel dichloride, dichloride [ bis- (1,3-diphenylphosphine) propane] nickel, dichloride, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphonium) palladium chloride, [bis- (l, 2-diphenylphosphine) dichloride) ] palladium, [bis- (1, 3-diphenylphosphine) propane] palladium chloride, and dichloride (diphenylphosphine) ethane and bis-1, 3- (diphenyl-phosphin) propane. Depending on how the reaction is effected there, compounds I are formed with -XR6 = hydrogen or C ^ Cj-alkyl or corresponding mixtures of alkylated and non-alkylated compound I, but which can be separated in the usual manner. In general, work is carried out at (-100) ° C up to the boiling temperature of the reaction mixture. The amount of the Grignard reagent is not critical; normally (Ci-Cg-alkyl) MgHal in approximately equimolar or excess amount, up to approximately the 10-fold molar amount, with respect to the amount of I with -XR6 = halogen, unless otherwise indicated, all procedures described above are conveniently carried out at atmospheric pressure or at the proper pressure of the respective reaction mixture The reconditioning of the reaction mixtures is generally carried out in a manner known per se, unless otherwise indicated in the procedures described above. , the products of value are obtained, for example, after diluting the reaction solution with water, by filtration, crystallization or extraction with a solvent or by elimination of the solvent, distribution of the residue in a mixture of water and an appropriate organic solvent and reconditioning the organic phase to obtain the product. if desired, they can be separated into the very pure isomers by means of the usual methods, for this, such as crystallization or chromatography, also in an optically active adsorbate. Advantageously, pure optically active isomers can be prepared from the corresponding optically active starting materials.

Agriculturally usable salts of the compounds I can be prepared by reaction with a corresponding cation base, preferably a hydroxide or alkali metal hydride or by reaction with a corresponding anion acid, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, acid phosphoric or nitric acid. Salts of I whose metal ion is not an alkali metal in can also be prepared by trans-salification of the corresponding alkali metal salt in a manner known per se, likewise salts of ammonium, phosphonium, sulfonium and sulfoxonium by means of ammonia, hydroxides of phosphonium, sulfonium and sulfoxonium. The compounds I and their agriculturally usable salts are suitable as herbicides, either as mixtures of isomers, or in the form of pure isomers. The herbicides containing the compounds I combat the growth of plants in uncultivated areas very well, especially by using a large amount. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and harmful herbs without damaging the cultivated plants. This effect occurs first of all using a small amount.

They should be applied more in a number of more crop plants to eliminate non-plants. eseadas For example, the following cements are included: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus offi-cinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tincto-rius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cyno-don dactylon, Daucus carota, Elaeis guineensis. Fragaria vesca, Glycine max, Gossypium hirsutum,. { Gossypium arboreum, Gossypium herbaceum, Gossypium vitífolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersi-cum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseo-lus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes syl-vestre, Ricinus communis, Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobro a cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays. In addition, compounds I can also be applied in crops that have become tolerant to the effect of herbicides.

In addition, the substituted (4-bromopyrazol-3-yl) benzazoles I are also suitable for desiccation and / or defoliation of plants. As desiccants, they are especially suitable for drying the aerial parts of crop plants such as potatoes, rapeseed, sunflower and soybeans. This allows a completely mechanical harvest of these important crop plants. In addition, it is of economic importance to facilitate the harvesting that is possible by means of the detachment concentrated over time or the reduction of the adherence to the tree in citrus fruits, olives or in other species of seed, stone and peel fruits. The same mechanism, that is, the promotion of the formation of separation tissue between the part of the fruit or leaf and the part of the shoot of the plants is also essential for a well controllable defoliation of useful plants, especially cotton. Furthermore, the shortening of the time interval, in which the individual cotton plants mature, leads to a better quality of the fiber after harvesting. The compounds I or, where appropriate, the agents containing them, can be applied, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, also aqueous, oily or other suspensions or dispersions, of high percentage, emulsions, oily dispersions, pastes, sprayable agents, spreadable or granulated agents, by means of spraying, spraying, spraying, spreading or watering. The forms of application m s na str uc n pos e e as their anc as act with ormes to the invention. «As inert auxiliary substances they essentially enter into consideration: Fractions of medium-high boiling mineral oil such as kerosene and diesel oil, coal tar oils, as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example, paraffins, tetrahydrofoam, ^ Dronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, for example, amines such as N-methylpyrrolidone and water. 15 Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or granules dispersible in water, by adding water. For the preparation of emulsions, pastes or oily dispersions substances can be homogenized in water in pure form or dissolved in an oil or solvent, by means of humectants, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of active substance, wetting agents, adhesives, dispersants or emulsifiers and optionally solvents or oil, which are suitable for dilution with water. As surfactants, for example, alkali metal, alkaline earth metal and ammonium salts of sulphonic acids are suitable. a-s, -rilsulfonates, algal sulfates, lauryl ether sulfates and fatty alcohols, as well as salts of sulfated hexa, hepta and octadecanols, as well as glycol ether of fatty alcohols, condensation products of sulfonated naphthalene and their derivatives with formaldehyde , condensation products of naphthalene or, where appropriate, of naphthalenesulfonic acids with phenol and formaldehyde, octylphenol ether of polyoxyethylene, isooctyl, octyl or nonylphenol ethoxylates, alkylphenyl- or tributylphenylpolyglycol ether, alkylarylpolyester alcohols, isotridecyl alcohol, alcohol condensates fatty acids with ethylene oxide, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, residual lignin sulphite liquors or methylcellulose. Powdered, spreadable or sprayable agents can be prepared by mixing or grinding together the active substances with a solid support. Granules, for example, covering, impregnation or homogeneous can be prepared by binding the active substances to solid support substances. Solid support substances are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite and diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, substances synthetic fertilizers, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas and products , solid support substances. The concentrations of the active substances I in ready preparations for Taar can be varied in wide ranges In general, the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active substance The active substances I are used here in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum) The following formulation examples explain the preparation of such preparations: I. 20 parts by weight of compound No. In. 003 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the addition product of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely dispersing the solution in 100000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

II- 20 parts by weight of the compound No. Im.003 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, Tylphenol and 10 parts by weight of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely dispersing the solution in 100000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

III. 20 parts by weight of the active substance No. Ik. 003 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a fraction of mineral oil boiling from 210 to 280 ° C and 10 parts by weight of the addition product of 40 moles. of ethylene oxide to 1 mol of castor oil. By pouring and finely dispersing the solution in 100000 parts by weight of water, an aqueous dispersion containing 0.02% of the active substance is obtained.

IV. 20 parts by weight of active substance No. It.003 are good And they are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulphonic acid, 17 parts by weight of the sodium salt of a lignin sulphonic acid of a residual sulphite liquor and 60 parts by weight of silica gel. powder and ground together in a hammer mill. By finely dispersing the mixture in 20,000 parts by weight of water, a spray liquid containing 0.1% by weight of the active substance is obtained. as with pair is in weight e ao n e par cu as nas. In this manner, a spray agent containing 3% by weight of active substance is obtained.

SAW. 20 parts by weight of the active substance No. Im.003 are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a of phenol-urea-formaldehyde and 68 parts by weight of a paraffinic mineral oil. A stable oil dispersion is obtained.

VII. 1 part by weight of compound No. Ik.003 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 ethoxylated castor oil. The mixture can then be diluted with water until the desired concentration of active substance is reached. A stable emulsion concentrate is obtained. VIII.1 part by weight of compound No. It.003 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (= non-ionic emulsifier based on ethoxylated castor oil; BASF AG). Then it can be diluted with water until reaching the desired concentration of active substance. A stable emulsion concentrate is obtained.

Compositions before the germination or the post-germination process. If the active substances for certain crop plants are less tolerable, application techniques can be used in which the herbicides are sprayed by sprinklers in such a way that the leaves of the delicate crop plants are not sprayed as much as possible., while active substances fall on leaves of unwanted plants that grow under or on bare ground (post-directed, lay-by). The amounts to be applied of active substance I amount, according to the target to be controlled, season of the year, plants to be protected and growth stage at 0.001 to 3.0, preferably from 0.01 to 1.0 Kg / ha of active substance ( ace). In order to broaden the spectrum of action and to achieve synergistic effects, the substituted (4-bromopyrazol-3-yl) benzazoles I can be mixed with numerous representatives of other groups of active herbicidal or growth-regulating substances and can be applied together. For example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, amino-triazoles, anuides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid, are suitable as mixing partners. and its derivatives, benzothiadiazinones, 2- (heteroaroyl / aroyl) -1, 3-cyclohexanediones, heteroaryl-apl-ketones, benzylisoxazolidinones, meta-CFj-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilide, derivatives with nuac n concentrate. After evaporation in ethyl acetate, the organic phase was washed with dilute aqueous sodium hydrogencarbonate solution, then dried over magnesium sulfate and finally concentrated. Purification of the crude product was carried out by chromatography on silica gel (eluent: hexane / ethyl acetate = 9: 1). Yield: 3.3 g MS [m / z]: 423 [M *]. 'H-NMR (400 MHz, in CDC13): d [ppm] = 1.45 (t, 3H), 2.98 (q, 2H), 3.92 (s, 3H), 6.74 (t, 1H), 7.24 (d, 1H).

Previous Step 1.1 4-bromo-3- (4-chloro-2-fluoro-5-nitrophenyl) -5-difluoromethoxy-1-methyl-1H-pyrazole To 16.6 g (0.26 mol) of concentrated nitric acid 15.5 g (0.16 mol) of concentrated sulfuric acid were added at (-30) ° C. After cooling to (-40) ° C, the mixture was added dropwise of a solution of 18.7 g (53 mmoles) of 4-bromo-3- (4-chloro-2-fluorophenyl) -5-difluoromethoxy-1. -methyl-lH-pyrazole in 100 ml of dichloromethane. The reaction mixture was then stirred for 4 h, after which it was poured into ice water. The organic phase was separated, washed with dilute aqueous sodium hydrogencarbonate solution and water, dried over magnesium sulfate and finally concentrated. Yield: 15.6 g. 'H-NMR (270 MHz, in CDClj): d [ppm] = 3.88 (s, 3H), 6.72 (t, 1H), 7.41 (d, 1H), 8.24 (d, 1 HOUR) . - - - - - - - - - - - - - -fluoraniline To a solution of 15.6 g (39 mmol) of 4-bromo-3- (4-chloro-2-fluoro-5-nitrophenyl) -5- d? fluormetox? -l-meth? l-lH-pyrazole in 150 ml of tetrahydrofuran 5 g of Raney nickel were added, after which was hydrogenated with slight overpressure of hydrogen until absorption of the calculated amount of hydrogen. The catalyst was then filtered off through a pad of Kieselguhr. The filtrate was concentrated. Performance: quantitative. 'H-NMR (400 MHz, in CDClj): d [ppm] = 3.85 (s, 3H), 3.97 (s, 2H), 6.70 (t, 1H), 6.89 (d, 1H), 7.12 (d, 1H).

Preliminary step 1.3 5- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -2-chloro-4-fluorophenylazide (No. Va.3) To a solution of 14.4 g ( 39 mmoles) of 5- (4-bromo-5-d? Fluoromethoxy-l-methyl-lH-p? Razol-3-yl) -2-chloro-4-fluoraniline in 60 ml of trifluoroacetic acid at 10-15 °. First, 6.0 g (59 mmol) of tert-butyl nitrite and then 3.8 g (59 mmol) of sodium azide were added, followed by stirring for one hour at about 20 ° C before pouring. reaction solution on ice. the product from the aqueous phase with methyl tert-butyl ether was extracted. Thereafter the organic phase was washed with aqueous sodium hydroxide solution 10%, dried over magnesium sulfate and finally concentrated, caring of not heating above 40 ° C . . , j,, 3H), 6.71 (t, 1H), 7.25 (d, 1H), 7.33 (d, 1H).

Example 2 7- (4-bromo-5-dif luormetoxy-l-met? L-lH-p? Razol-3-? L) -4,6-dichloro-2-ethylbenzoxazole (Compound No. Im.003) This compound was prepared analogously to example 1.? -NMR (270 MHz, in CDC13): d [ppm] = 1.43 (t, 3H), 2.97 (q, 2H), 3.92 (s, 3H) 6.75 (t, 1H), 7.49 (s, 1H).

Preliminary step 2.1 4-Bromo-3- (2,4-dichloro-5-nitrophenyl) -5-difluoromethoxy-1-methyl-1H-pyrazole This compound was prepared analogously to the previous step 1.1. ? -NMR (270 MHz, in CDClj): d [ppm] = 3.88 (s, 3H), 6.72 (t, 1H), 7. 71 (s, 1H), 8.04 (s, 1H).

Previous step 2. 5- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -2,4-dichloroaniline This compound was prepared analogously to the previous step 1.2. ? -NMR (270 MHZ, in CDClj): d [ppm] = 3.84 (s, 3H), 4.12 (s, 2H), 6. 72 (t, 1H), 6.79 (s, 1H), 7.38 (s, 1H). , - - - - - - - - lH-p? razol-3-ilo) (No. Va .2) This compound was prepared analogously to the previous step 1.3. 5 MS [m / z]: 411 [M *]. 'H-NMR (270 MHz, in CDCl,): d [ppm] = 3.87 (s, 3H), 6, 72 (t, 1H), 7, 21 (s, 1H), 7, 52 (s, 1H).

Example 3 7- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-chloro-2-yl-ethyl-benzoxazole (Compound No. Ik.003) This compound was prepared analogously to example 1.? -NMR (270 MHz, in CDC13): d [ppm] = 1.48 (t, 3H), 3.03 (q, 2H), 3.92 (s, 3H), 6.74 ( t, 1H), 7.40 (d, 1H), 7.55 (d, 1H).

Preliminary step 3.1 4-bromo-3- (4-chlorophen? L) -5-d? Fluormetox? -l-methyl-2H-p? Razol To a solution of 10.1 g (39 mmol) of 3- ( 4-chlorophenyl) -5- d? Fluormetox? -1-met? L-lH-p? Razol in 100 ml of tetrachloromethane was added 7.9 g (43 mmol) of bromine, after which it was stirred for 16 hs. After this the solution was washed with saturated aqueous sodium hydrogencarbonate solution, dried over magnesium sulfate and finally concentrated. Yield: 12.9 g. ? - NMR (270 MHz, in CDCl.,): D [ppm] = 3.84 (s, 3H), 6.69 (t, 1H), 7.40 (d, 2H), 7.81 (d , 2H). 96 líf •• "• - **» * - '"c ~ - romo- - -c oro- -n ro en - - uorme ox - --me - - pyrazole This compound was prepared analogously to the previous step 1.1. 'H-NMR (270 MHz, in CDCl 3): d [ppm] = 3.86 (s, 3H), 6.70 (t, 1H), 7.40 (d, 1H), 8.08 (dd, 1H), 8.46 (d, 1H).

Preliminary step 3.3 5- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazole-3?) -2-chloroaniline To a suspension of 10.2 g (0.18 mol) of iron powder in 30 ml of acetic acid and 50 ml of ethanol, heated to 70-75 ° C, 11.7 g (35 mmoles) of 4-bromo-3- (4-chloro-3-nitrophenyl) -5- were added portionwise. difluoromethoxy-1-methyl-1H-pyrazole. It was then heated for 2 hours at reflux temperature. After cooling ethyl acetate was added, before filtering the solution through a pad of Kieselguhr. The filtrate was washed with saturated aqueous sodium hydrogencarbonate solution and water, then dried over magnesium sulfate and finally concentrated. Performance: quantitative. 'H-MNR (400 MHz, in CDC13): d [ppm] = 3.81 (s, 3H), 4.12 (s, 2H), 6.68 (t, 1H), 7.19 (dd, 1H), 7.26 (d, 1H), 7.29 (d, 1H).

Step 3.4 3.4-Chlorophenylazide of 5- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) (No. Va.l) This compound was prepared analogously to the previous step 1.3. - - - - - - - - - -l - -c oro- -ethyl-6-fluorbenzoxazole (N ° It.003) This compound was prepared analogously to Example 1.? -NMR (400 MHz, in CDClj): d [ppm] = 1.45 (t, 3H), 2.98 (q, 2H), 3.36 (s, 3H), 4.32 (s, 3H), 7.27 (d, 1H).

Preliminary step 4.1 4-bromo-3- (4-chloro-2-fluorophenyl) -l-met? L-5-met? Lt? S-lH-p? Razol To a solution of 20 g (78 mmoles) of 3 - (4-Chloro-2-fluorophenyl) -l-4-methyl-5-methoxy-1H-pyrazole in 400 ml of tetrachloromethane was added dropwise to 13.7 g (86 mmol) of bromine, after which it was stirred for 3 days. The reaction solution was then washed with saturated aqueous sodium hydrogencarbonate solution and water, dried over magnesium sulfate and finally concentrated. Purification of the crude product was carried out by chromatography on silica gel (eluent: hexane / ethyl acetate = 9: 1). Yield: 22.4 g. ? -NMR (270 MHz, in CDCl3): d [ppm] = 2.40 (s, 3H), 4.06 (s, 3H), 7.15-7.25 (m, 2H), 7.48 (t, 1H).

Preliminary step 4.2 4-bromo-3- (4-chloro-2-fluorophenyl) -l-methyl-5-methylsulfonyl-1H-pyrazole To a solution of 22.4 g (67 mmol) of 4-bromo-3- ( 4-chloro-2-fluorophenyl) -l-methyl-5-methylthio-1H-pyrazole in 300 ml of dichloromethane The reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution, saturated solution of Na2S203 and water, dried over sulphate, and then stirred for 16 hours at about 20 ° C. magnesium and finally concentrated Yield: 17.7 g.? -NMR (270 MHz, in CDC1¡): d [ppm] = 3.32 (s, 3H), 4.27 (s, 3H), 7 , 20-7.28 (m, 2H), 7.41 (t, 1H).

Preliminary step 4.3 4-bromo-3- (4-chloro-2-fluoro-5-nitrophenyl) -l-methyl-5-methylsulfonyl-1H-pyrazole This compound was prepared analogously to the previous step 1.1. 'H-NMR (270 MHz, in CDC13): d [ppm] = 3.33 (s, 3H), 4.29 (s, 3H), 7.44 (d, 1H), 8.20 (d, 1 HOUR) .

Preliminary step 4.4 5- (4-bromo-1-methyl-5-methylsulfonyl-1H-pyrazol-3-yl) -2-chloro-4-fluoraniline This compound was prepared analogously to the previous step 1.2. 'H-NMR. { 270 MHz, in (CD3) 2S?): D [ppm] = 3.47 (s, 3H), 4.17 (s, 3H), 5.43 (s, 2H), 6.88 (d, 1H ), 7.34 (d, 1H). ^ É ^ - 4-bromo-1-methy-5-met lsu on-lH-p-razol-3-yl) -2-chloro-4-fluorophenylazide (No. Va.9) This compound was prepared analogously to the previous step 1.3. MS [m / z]: 407 [M *]. 'H-NMR (400 MHz, in CDC13): d [ppm] = 3.32 (s, 3H), 4.28 (s, 3H), 7.28 (m, 2H).

Example 5 2-amino-7- (4-broms-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-chloro-6-fluorobenzthiazole (Compound No. Ic.080) To a solution of 4 7 g (13 mmol) of 5- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -2-chloro-4-flusraniline in 100 ml of acetic acid were added 4.1 g (50 mmol) of thiocyanate sodium. After stirring for 10 minutes, 4 g (25 mmol) of bromine was added dropwise to the mixture. It was then stirred for 16 h. The reaction mixture was then poured into water. Finally, the product of solid value formed was filtered off and dried. Performance: quantitative. 'H-NMR (270 MHz, in CDC13): d [ppm] = 3.87 (s, 3H), 6.20 (s, 2H), 6.74 (t, 1H), 7.24 (d, 1 HOUR) .

Example 6 7- (4-Bromo-5-difluoromethyl-l-methyl-lH-pyrazol-3-yl) -4-chloro-6-fluoro-2- (methylthio) benzthiazole (Compound No. Ic.099) A solution of 1.5 g (3.5 mmol) of 2-amino-7- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-chloro-6-fluorobenzthiazole in mraols) of dimethyl disulfide and 1.08 g (7 mmol) of tert-butyl nitrite. After 16 h the solution was concentrated and the residue was purified by chromatography on silica gel. Yield 0.4 g. 'H-NMR (270 MHz, in CDClj): d [ppm] = 2.80 (s, 3H), 3.90 (s, 3H), 6.74 (t, 1H), 7.34 (d, 1 HOUR) .

Example 7: 2-bromo-7- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-chloro-6-fluorobenzthiazole (Compound No. Ic.041) A solution of 1.5 g (3.5 mmol) of 2-amino-7- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-chloro-6-fluorobenzthiazole in 50 ml of acetonitrile was added with 1.8 g (17.5 mmoles) of sodium bromide, 1 g (7 mmoles) of copper bromide (I) and 0.47 g (4.6 mmoles) of tert-butyl nitrite. After 16 hrs, 50 ml of dilute hydrochloric acid was added, the precipitate was separated by filtration and rinsed with ethyl acetate. The filtrate phases were separated, the aqueous phase was extracted twice with ethyl acetate, the combined nic phases were dried over MgSO 4, filtered and concentrated. The crude product was purified by chromatography on silica gel. Yield 0.4 g. MS [m / z]: 489 [M *]. 7- 4- romo-5- uormetoxi-l-met-lH-p razol-3- l) -4-chloro-6-fluoro-2-methoxybenzthiazole 60 mg of sodium were dissolved in 20 ml of methanol and then added of 0.4 g (1 mmol) of 2-bromo-7- (4-bromo-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl) -4-chloro-6-fluorobenzthiazole. After 1 hour, concentrate and purify the crude product by chromatography on silica gel (eluent: cyclohexane / ethyl acetate 4: 1). Yield 0.4 g. ? -NMR (270 MHz, in CDClj): d [ppm] = 3.88 (s, 3H), 4.13 (s, 3H), 6.74 (t, 1H), 7.29 (d, 1H) ).

Application examples (herbicidal effect) The herbicidal effect of the substituted pyrazol-3-ylbenzazoles I could be demonstrated by means of the following greenhouse tests: As plastic culture pots with muddy sand, about 3.0% humus as a substrate. The seeds of the test plants were seeded separately by species. In the treatment before germination the active substances suspended or emulsified in water were applied directly after sowing by means of finely dispersing sprinklers. The containers were lightly wet with fine rain to encourage germination and growth, and were then covered with transparent plastic caps, until has suffered detriment by action of the active substances.

With the finalisation of a post-germination treatment, the test plants were captivated, according to their growth pattern, up to a height of 3 to 15 cm. and then treated with the active substances suspended or emulsified in water. For this purpose, the test plants were either directly sown and cultivated in the same containers or were first cultivated as separate storehouses and transplanted some days before treatment in the test vessels. The plants were maintained according to the species at temperatures of 10 to 25 ° C or, where appropriate, from 20 to 35 ° C. The trial period was extended for 2 to 4 weeks. During this time the plants were taken care of, and their reaction to the different treatments was evaluated.

The assessment was made on a scale from 0 to 100. 100 in this case, means that the plants have not germinated or, where appropriate, that at least the aerial parts have been totally destroyed, and 0 means that there has been no damage or there is normal development of growth.

Application examples (desiccant / defoliant effect) Young cotton plants with 4 leaves (without germination leaves) that were grown under greenhouse conditions (relative humidity of 50 to 70%, day / night temperature 27) were used as test plants. / 20 ° C). The young cotton plants were treated in their leaves, , of Plurafac® f 700 fatty alcohol "referred to the spray liquid The amount of water employed was, after the conversion, of 1000 1 / ha.After 13 days the amount of fallen leaves and the degree of defoliation were determined in%. In the untreated control plants there was no leaf fall '"A low-foaming, non-ionic surfactant from BASF AG.

Claims (5)

1. R E I V I N D I CA C I O N E S 1.
2. Compounds of (4-bromop? Razol-3-? L) substituted benzazoles CHARACTERIZED because they have the formula I in which the variables have the following meanings R1 hydrogen, Cj-Cj-alkyl or C, -C, -halogenoalkyl, 15 R2 cyano, C, -C, -alkyl, Cj-Cj-haloalkyl, C, -C, -alcox? , C, -C, -halogenalcox ?, C, -Cj-alkyl?, C, -C, -alkylsulfinyl, C, -C, -haloalkyl-sulfinyl, Cj-C, -alkylsulfonyl or Cj-C. -halogenoalkylsulfonyl, R * hydrogen or halogen, Rs hydrogen, halogen, cyano, C, -C4-alkyl, C, -C, -haloalkyl, C3-C4-alkoxy? or Z a group -N = C (XR6) -O- or -N = C (XR6) -S-, which may be attached by means of nitrogen, oxygen or sulfur to a, 105 iirtr - - ^ - "l? < BÍit B £ a? Tfi-Ml ^ i-i - i R5, R7, independently of each other, Cj-C3-alkyl, j-Cj-haloalkyl, cyano-Cj-C, -alkyl, hydroxy-Cj-Cj-alkyl, C-C6-alkenyl, cyano-Cj- C6 -alkenyl, Cj-C6 -halogenoalkenyl, Cj-C6-alkynyl, cyano-C6-alkynyl, C3-C6-haloalkynyl, Cj-C, -alkoxy-Cj-Cj -alkyl, Cj-C4 -halogenoalkoxy- C1-C1-alkyl, Cj-C4-alkenyloxy-d-C4-alkyl, Cj-C4-alkynyloxy-Cj-C4 -alkyl, Cj-C-β-cycloalkyloxy-C3-C4-alkyl, amino-C3-C4- alkyl, Cj-C4 -alkylamino -Cj-C4- alkyl, di (Cj-Cj-alkyl) amino-Cj-C ^ alkylene, Cj-Cj-alkylthio-Cj-C-alkyl, C3-C (- haloalkyl-alkyl-Cj-C-alkyl, C 1 -C 4 -alkenylthio-Cj-C, -alkyl, C 3 -C, -alkynyl-thio-C 3 -C -alkyl, C 3 -C "-alkynyl sulfyl- Cj- Cj-alkyl, C, -C "- halogenoalkylsulphyl inyl -Cj-C, -alkyl, C 1 -C 4 -alkenylsulphyl-Cj-C 4 -alkyl, Cj-C 4 -alkynylsulphyl-C 3 -C 4 -alkyl, C, - C4-alkylsulfonyl-Cj-C4-alkyl, C, -C4-halogen-alkylsulfonyl-Cj-C4-alkyl, C, -C4-alkenyl sulf onyl-Cj-C4-alkylo, C3- C4- alqui - - j 4, 1-, - - -Cs'jC4-alkyl, which may carry a cyano group or (Cj-C-alkoxy) carbonyl, (C! -C4-alkylthio) carbonyl-C1-C-alkyl, amino- carbonyl-Cj-Cj-alkyl, Cj-Cj-alkylamino-carbonyl-Cj-C-alkyl, di (C1-C4-alkyl) -aminocarbonyl-C, C4-alkyl, di (Cj-C4-alkyl) -phosphonyl- Cj-Cj-alkyl, (Cj-C4-alkoxy) imino-Cj-C4-alkyl, (C 1 -C 4 -alkeni -loxy) imino-C 3 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 3 -C0 -cycloalkyl -Cj-C4 -alkyl, phenyl, phenyl-Cj-C4-alkyl, heterocyclyl or heterocyclyl-Cj-C4-alkyl of 3 to 7 links, wherein each cycloalkyl ring and each heterocyclyl ring may contain a ring link carbonyl or thiocarbonyl, wherein each cycloalkyl, phenyl and heterocyclyl ring can be unsubstituted or can carry from one to four substituents, each selected from the group consisting of cyano, nitro, amino, hydroxy, carboxy, halogen, Cj-C4-alkyl , Cj-C4-haloalkyl, C1-C4-alkoxy, C, -C4-haloalkoxy, Cj-C4-alkylthio, Cj-C, -halogenalkylthio, C-C4 -alkylsulfonyl, mu r > ra ^ (C 1 -C 4 -haloalkyl) carbonyl, (C, -C, -alkyl) carbonyloxy, (C 1 -C 4 -haloalkylcarbonyloxy and di (C 1 -C 4 -alkyl) amino, provided that X is a bond chemistry, oxygen, sulfur, -NH- or -N (R7) -, then Rs can also mean (Cj-C4-alkyl) carbonyl, (Cj-C4-haloalkyl) -carbonyl, (C1-C4-alkoxy) carbonyl, C, -C 4 -alkylsulfonyl or Cj-Cj-haloalkylsulphonyl, provided that X is a chemical bond, then Rs can also mean hydrogen, cyano, mercapto, animo, halogen, -CH2-CH (halogen) -R8, - CH = CH-R8 or -CH = C (halogen) -R8, where Ra represents hydroxycarbonyl, (Cj-C4-alkoxy) carbom, (C1-C4-alkylthio) carbonyl, ammocarbonyl, Cj-Cj-alkylaminocarbonyl, ditCj -C, -alkyl) aminocarbonyl or od (Cj-C4-alkyl) phosphonyl; or R6 and R 'together represent a 1,3-propylene, te-tramethylene, pentamethylene or ethyleneoxyethylene chain, each of which may be unsubstituted or may carry one to four Cj-C4-alkyl groups one or two groups (C3-C4-alkoxy) carbonyl, as well as the agriculturally usable salts of I. substituted aminobenzazoles and their agriculturally utilizable salts, according to claim 1, characterized in that the drying / defoliation of plants or their application as herbicides.
3. 3. - CHARACTERIZED herbicidal compositions because they have herbicidally effective amounts of at least one substituted (4-bromopyrazol-3-yl) benzazole of formula I or of a salt F $ agriculturally usable of I, according to claim 1, and at least one liquid or solid inert carrier or support, as well as, if desired, at least one surfactant.
4. 4. - Agents for the desiccation and / or defoliation of plants, CHARACTERIZED because they contain effective amounts as desiccants and / or defoliants of at least one (4-bromopyrazol-3-substituted iUbenzazole of formula I or of agriculturally usable salts of said compounds (I) according to claim 1, and at least one liquid and / or solid inert carrier or support, as well as, if desired, at least one surfactant.
5. 5. Process for preparing compositions with herbicidal effect, CHARACTERIZED by mixing amounts of herbicidal effect of at least one substituted (4-bromopyrazol-3-yl) benzazole of formula I or of agriculturally utilizable salts of IO 3 co. (I), according to claim 1, with at least one vehicle 6. - Process for preparing compositions of desiccant and / or defoliant effect, CHARACTERIZED in that effective amounts are mixed as desiccants / defoliants of at least one substituted (4-bromopyrazol-3-yl) benzazole of formula I or of agriculturally usable salts thereof, according to claim 1, with at least one liquid and / or solid inert carrier or support, as well as, if desired, with at least one surfactant. 7. - Process to combat the unwanted growth of plants, CHARACTERIZED because effective amounts are actuated as a herbicide of at least one substituted (4-bromopyrazol-3-yl) benzazole of formula I or of an agropeculently useful salt thereof, in accordance with Claim 1, on plants, their habitat or on seeds. i itniirt - ** " 10. - Process for the preparation of substituted (4-bromop? Razol-3-yl) benzazoles of formula I according to claim 1, wherein Z represents -N = C (R *) - 0-, CHARACTERIZED by diazotizing an aminophenyl-pyrazole of Illa formula or 11Ib the diazonium salt formed with an alkali metal azide is transformed to obtain an azidophenylpyrazole of formula Va or Vb and finally it is reacted with a carboxylic acid of formula R6-C00H. 11. - Intermediary compounds for application in the process of claim 1, CHARACTERIZED because they are azidofe-nilpyrazoles of formula Va or Vb jm ^ & g¡l¡