Derived from benzazole, their therapeutic preparation and their uses.
The the benzazcle, of proceeded for its T-I-e is the th•'•the Ra; had T-I-fitting it is checked. provides the new 1st■ - utiîi res. derivatives I The compounds of the invention correspond to formula THE R " - C-NH VBE1> - PH value - R.the Z 5 3 (I-) wherein represents a piperazino group optionally substituted in position 4, or a group of the formula R2- Alk-X2- *" represents an optionally esterified carboxyl group or hydroxymethyl group, alk represents a lower alkylene group or lower alkylidene, the X ^ and named xG each represent, independently of one another, oxygen or sulfur, pH is a group 1,2- phénylêne optionally having substituent other than the group Η ^ - ℮ (≈ Χ ^) - - ΚΗ, xi represents oxygen, the. sulfur or an imino group optionally substituted and represents a lower alkyl group or cycloalkyl which is optionally substituted by fluoro substituents; the invention also includes the salts of these compounds, pharmaceutical compositions containing these compounds and their use. The substituents of the piperazino group are for example a lower alkyl group substituted by a hydroxy group at position farther than the alpha position, for example in position 4 of a group 4 - (lower alkyl) - piperazino, or an oxido group. Therefore, a piperazino group optionally substituted in position 4 is e.g. a group 1-piperazino, the L - (4-lower alkyl) - piperazino or 1 - (4-lower alkyl-4-oxido) - piperazino or 1 - [4 - (hydroxy lower alkyl)] piperazino -, the hydroxy group being in position farther than the alpha position. Esterified carboxy is for instance an group (lower alkoxy) - carbonyl. Among the additional substituents pH, include for example the lower alkyl groups, lower alkoxy, lower alkanoyl, and/or the trifluorocéthyle halogen atoms. An imino group optionally substituted iiaino group is an unsubstituted or substituted for example by an oxido group, a lower alkyl group,, lower phenylalkyl or optionally substituted phenyl, lower acyl or lower àlcényle, e.g. lower alkanoyl, (lower alkoxy) - carbonyl, (lower alkane) sulfonyl -, the mono - or di - (lower alkyl) carbamoyl or àlkylène - or 3an aza - -, 3- oxa-- or j-thia alkylènecarbaraoyle containing 5 to 8 links in the cycle. The substituents of the lower alkyl group are for example groups of di - (lower alkyl) - amino and the substituents of a phenyl group or the phenyl moiety of phenylalkyl lower are for example lower alkyl groups, lower alkoxy and/or halogen atoms. Therefore, an imino group substituted is for instance an group (lower alkyl) - substituted imino, the imino (lower àlcényle) -, phenyl - or phenyl (lower alkyl) - imino optionally substituted as indicated above, (lower alkane) - sulfonylimino, a mono - or di - (lower alkyl) - or - carbamoyliminoàlkylène or 2an aza - -, 3- oxaou3- thia alkylene - carbamoylimino containing 5 to 8 ring members. A çycloalkyle group is for example a cycloalkyl group of 3 th 8 links such as cyclopentyl, cyclohexyl or cycloheptyl or cyclopropyl, cyclobutyl or cÿciooctyle. Panels all of the foregoing and in all that follows, the organic groups are "lower" qualified such as those containing up to? carbon atoms inclusive and preferably up to 4 carbon atoms inclusive. A lower alkyl group may be straight chained or branched and fixed in any position; in the case of it is preferably a straight chain lower alkyl group connected through a secondary carbon atom or group branched lower alkyl, preferably branched alpha or beta, and further preferably straight chain, connected by a primary or secondary carbon atom. As lower alkyl group connected via a primary carbon atom, examples for example methyl, ethyl, 1propyl -, ' Mratyle or 1- (2- mêthyl) - butyl, and also 1- pentyl, 1- hexyl ' or 1-heptyl. A watershed straight chain lower alkyl groups linked by an atom, ... secondary carbon in e. g. the groups 2- propyl and 2- butyl but also 23 - pentyl and -, 2 - and 3-hexyl or 2 -, 3 - and 4-heptyl. I ^ üq branched lower alkyl-IER is for example a tert-butyl or isobutyl, or 2- (2- methyl) - butyl, 3-<3- methyl) pentyl or 2- (3- ethyl) - pentyl. Group 1 - (4-lower alkyl) - piperazino group is for example a 4-methyl -, 4-ethyl -, 4 propyl -, 4 a-isopropylou 4 butyl -, 4 sec-butyl--, 4 isobutyl - or 4 tert-piperazino or 4 pentyl -, 4 hexyl - or 4-heptyl--piperazino. Of Be similarly "group 1 - (4-lower alkyl-4-oxido) piperazino is e.g. a group 4-methyl -, 4 ethyl 4 propyl -, 4 ISO-propyl - or 4 butyl -, 4 sec-butyl--" 4 a-isobutylou 4 tert-butyl 4 a-oaydo-piperazino or 4 pentyl -, 4 - ethylhexyl - or 4-heptyl-to-4-oxido-piperazino. A group - 1 [4 - (hydroxy lower alkyl)] piperazino - wherein the hydroxy group is in position farther than the alpha position is e.g. a group 1 - [4 - (2 hydroxyethyl)} - 1 or - [4 - (3 a-propyl)] piperazino~. A lower alkylidene group is for example a methylene, ethylidene, isopropylidene or 1,1- or 2,2- butylidene or pentylidene, hexylidene or heptylidène * A lower alkylene group is e.g. an ethylene group, - 1.2 1.2 or 1.3-propylene or -, 1, 3 - or 1.4-butylene or pentylene yet, hexylene or heptylene. Lower phenylalkyl is for example benzyl, 1- or 2- phenylethyl or 1-, 2- or 3- phenylpropyl, phenylbutyl or otherwise. A lower alkenyl is for example an allyl group or a group 2- or 3- butenyl. Lower alkoxy is for example methoxy, ethoxy, propyloxy, isopropyloxy group, -butyloxy, isobutyloxy sec-butyloxy, tert-butyloxy or, or pentyloxy, or heptyloxy hexyoxy. Of Be similarly, a (lower alkoxy) carbonyl group is for example a methoxy-,.éthoxy -, propyloxy - dihydroiso-propyloxy, --butyloxy, sec-butyloxy -, iso-butyloxy - or tert-pentyloxy or -, alkyloxy - or ethylhexyl heptyloxycarbonyle. A group is for example a aloanoyleiRXürieurîoroyle group, acetyl, propionyle,-to-butytyle, - iso butyryié " or still - pentanoyl, for example pivaloyl, heptanoyl or hexancyle. A group of di - (lower alkyl) - anino is e.g. a group substituted dimethyl - or diethyl-amino, correspondingly, a di - (alkyl inféi reporter *) - (lower alkyl) - aaino - the imino is e.g. a dimethylamino group - or diethyl aminomethylbenzolsulfonamide *" - or imino or especially dimethylamino2- (diethylamino) - éthy1the imino. A lower alkylimino group is for example a methyl -, ethyl -, hydroxypropyl -, ISO-propyl - or butyl-substituted imino. A group is for example a lower alcényliminoallylinino group. Phenyl-Calkyl lower) - alkoxyimino group is for example a benzyl - or 2the Thyl-imino-phenylated -. A lower alcanoylimino group is for example a - acetyl group, propionyl--, - butyryl-, ISO-butyryl - or pivaloylimino. A group (lower alkoxy) - carbonylimino is e.g. methoxy -, ethoxy -, - propyloxy, iso propyloxy -, --butyloxy or tert-carbonylimino. A group (lower alkane) - suifonylimino is for example a methane - or ethane-suifonylimino. Mono - or di - (lower alkyl) - carbamoylimino is for example a methyl -, ethyl - or diméthylcarbamoylimino. An alkylene group - or 3 aza -, a j-DXB - or 3-thia alkylene-carbanoy1the imino-containing 3 O 6 ring members is for example pyrrolidino -, piperidino -, - the morpholino, thiomorpholino or piperazino - - or 4-methyl-piperazino -, 4-methyl 4-oxido-piperazino - or 4 - (2 hydroxyethyl) - piperazino-carbonyl-the imino. Halogen is for example a halogen with an atomic number up to 35 included such as chlorine, but also fluorine or bromine. &its salts of the compounds of formula 1 examples of pharmaceutically acceptable salts for pharmaceutical use, for example salts forced by acid addition or, in the case '. of acid compounds, and for example of those for which represents a remainder R ^ - ^ - alk-X and The invention relates for example compounds of formula I wherein represents a group optionally substituted 1-piperazino at position 4 by lower alkyl, hydroxy lower alkyl wherein the hydroxy group is in position farther than the alpha position, and/or oxidation, or on the other hand a radical of the formula RG are-Alk named xG ^ - wherein R represents a carboxyl group optionally esterified with a lower alkanol or a group hydroxyœéthyle, alk represents a lower alkylene group or lower alkylidene and X ^ represents a thio-bridged or oxy, represents a thioxo group or ' oxoalcohols "•Ph represents a group 1*2- phênylcme carry endeavor LLemeht as substituents, in addition to the group Η ^ -0(≈ Χ ^) - α Η -, lower alkyl groups, lower alkoxy, lower alkanoyl, halogen and/or trifluoronéthyle, xi represents a bridge alkyloxy, fchio or imino optionally having substituents may go lower, the di - (lower alkyl) - (lower alkyl) - anino, phenyl optionally substituted by lower alkyl groups, lower alkoxy •and/or halogens or lower phenylalkyl, lower alkenyl, lower alkanoyl, lower alkoxycarbonyl, esulfonylealcar. lower, a mono - or di-Calkyl IFN greatly accelerated laugh) alkylene - or - carbaœoyle or 3an aza -. -, . 3- oxa-- or j-thia alkylene-carbamoyl containing 5 to 8 ring members, ^ and R represents a lower alkyl group optionally having substituents fluoro or a cycloalkyl group of 3 to 8 membered, and their salts, in particular pharmaceutically acceptable salts for pharmaceutical use. The present invention relates firstly to compounds of the formula wherein R ^ represents a group 1- piperazino -, 1 - (4 alkyl-lower) - piperazino containing up to 4 carbon atoms included in the lower alkyl group, for example 1 - (4-methyl) - piperazino, 1 - (4-alkyl drops and 4-oxido) - piperazino containing up to 4 carbon atoms included in the lower alkyl part, for example 1 - (4 a-Béthyl-to-4-oxido) piperazin © or 1- [4 - (hydroxy lower alkyl)] piperazino - wherein the hydroxy group is in position farther than the alpha position and the hydroxy-lower alkyl group contains up to 4 carbon atoms inclusive, for example 1 - (4 - (2 hydroxyethyl)] piperazino -, or on the other hand a group of the formula RIPs-to-àlk ' a-named xG ^ - wherein R represents a carboxy group or lower alkoxycarbonyl containing total up to 5 carbon atoms inclusive, for example méthoxyearbonyle or ethoxycarbonyl, or hyeroxyméthyle, alk-' represents a lower alkylene group containing up to 4 carbon muted included, e.g. ethylene or 1,5- propylene, and X ^ represents oxygen or, preferably, sulfur, and R ^ represents hydrogen, a lower alkyl group containing up to 4 carbon muted included such as methyl, lower alkoxy containing up to 4 carbon muted included as methoxy or halogen with an atomic number up to 55 included such as chlorine, the X ' j represents an oxy bridge, fchio, the imino, alkylimino lower containing up to 4 carbon atoms inclusive as methylimino, (alkane thein the £distinctiveness) - sulfonylimino containing up to 4 carbon atoms inclusive as methane-sulfonylimino, (lower alkoxy) - carbonylimino containing up to 5 muted carbon included as éthoxycarbonylimino, a di (lower alkyl) -~carbamoylimino containing up to 8 carbon atoms inclusive as diméthyIcarbamoylimino, or phenyl (lower alkyl) - imino-containing up to 10 carbon atoms inclusive as benzylimino, ^ and R represents a lower alkyl group branched alpha or straight chain connected by a secondary carbon atom which contains up to 4 carbon atoms inclusive as tert butyl or isopropyl -, and their salts, in particular pharmaceutically acceptable salts for pharmaceutical use * The invention particularly relates to compounds of formula la represents a group 1 - (4-lower alkyl) - piperazino group containing up to 4 carbon atoms included in the lower alkyl group, for example 1 - (4-methyl) - piperazino, 1 - (4-lower alkyl-4-oxido) piperazino containing up to 4 carbon atoms included in the lower alkyl group, for example 1 - (4 methyl-4-oxido) - piperazino, or 1 - [4 - (hydroxy lower alkyl)] piperazino - wherein the hydroxy group is attached at position farther than the alpha position and the hydroxy lower alkyl group contains up to 4 carbon atoms inclusive, for example 1 - [4 - (2 hydroxyethyl)] piperazino -, or on the other hand a group of the formula R - alk-' a-named xG ^ - ^ in which R represents a carboxy group or lower alkoxy carbonyl containing total up to 5 carbon atoms includes, for example methoxycarbonyl or ethoxycarbonyl, Aik•represents a lower alkylene group containing up to 4 carbon muted included as ethylene or *1, propylene and ^ is sulfur, and R ^ represents hydrogen, a lower alkyl group containing up to 4 muted carbon included such as methyl, lower alkoxy containing up to 4 carbon muted included such as methoxy, or halogen with an atomic number up to 35 included such as chlorine, the X ' represents a thio-bridged ^ ^ and R is a lower alkyl group branched alpha or straight chain connected by a secondary carbon atom containing up to 4 carbon atoms inclusive, for example tert-butyl or isopropyl, and their The invention relates above all the compounds that are of the formula in which R represents the ^ a group 1 - (4-lower alkyl) "- piperazino containing up to 4' carbon atoms included in the part lower alkyl, e.g. 1 - methyl (4") - piperazino or other hand a group ornéga-carboxy-lower alkylthio containing up to 4 carbon atoms included in the lower alkyl part, for example 2- carboxyethyl-thio group, and R ^ represents hydrogen, a lower alkyl or lower alkoxy group each containing up to 4 carbon atoms inclusive, for example methoxy or methyl, the X ' j represents a thio-bridged ^ and R represents a lower alkyl group branched alpha containing up to 4 carbon atoms inclusive, for example tert-butyl, and their salts. The invention relates particularly to compounds of formula I mentioned in the examples and their salts. The compounds of formula I can be prepared by methods known per se, for example by condensing together the; compounds of formulas (Ll) and ^ the X vBE1 there ' in which represents hydrogen and Y ^ ^ and Y together form a group of the formula " c * x ^ or one of the symbols Υ ^ and or salts thereof and, if desired, converting a resulting compound according to the invention into another compound of formula I and/or a free compound obtained in accordance with the invention into a salt or a salt obtained according to the invention in the free compound or another salt. The remainder élininable ^ there is e.g. an optionally esterified or etherified hydroxy group, a mercapto group or an optionally etherified trimethylammonioethyl quaternary group. An esterified hydroxy group is for example a hydroxyl group esterified by an organic carboxylic acid, among others a lower alkanoyloxy such as acetoxy group or a benzoyloxy group, but preferably a reactive esterified hydroxy group such as halogen, for example chlorine bromine curls. Etherified hydroxy is for example lower alkoxy or benzyloxy or phenoxy. Similarly, an etherified aercapto group is for example a lower alkylthio group, benzylthiopropionic or phenylthio. A group is for example a quaternary trimethylammonioethyl tri - (lower alkyl) - asmonio, for example trimethyl - or triéthylèamaonio, or pyridine. Fartant compounds of formula II wherein represents an optionally substituted 1-piperazino group in position 4, the remainder eliminable can also consist of a primary amino group, secondary or tertiary, for example an amino, n-mono - or n, n-di - (lower alkyl) - aœino, e.g. methyl - or ethyl-amino dimethylou or diethyl-amino, K., n-alkylene-amino compounds such as piperidino, pyrrolidino groups, the morpholino, thiomorpholino, or alternatively a group auïilino or diphenylamino. A benzoyloxy group, a benzyloxy, phenoxy, phenylthio, pyridine, aniline and diphenylamino as well as the phenyl ring groups benzyloxy and benzylthiopropionic, can still be substituted for example by AE lower alkyl groups, lower alkoxy, halogen and/or nitro groups. The salts of the starting compounds of formula II and III are for example metal salts of compounds of formula II wherein R " j represents a group HGGC-Alk the X ^, for example alkali metal salts or alkaline earth metal, among other salts or potassium sodiuc, of these compounds ., or the salts of compounds of formula II in ' which represents 1-piperazino optionally substituted in position 4 and represents 1' hydrogen, or the salts of compounds of formula III wherein Y2 represents a group -0(Χ=^) - Υ ^ or 1' * yj is hydrogen 1' hydrogen and Y ^ estêrifié reactive hydroxy, formed by acid addition, e.g. mineral acids, as in the case of halcgénhydrates, for example the hydrochlorides or hydrobromides, or salts of sulfuric acid, for example the bisulfate. The reaction is carried out in the usual manner and known in particular in technical literature for similar reactions, preferably in a solvent, such as a lower alkanol, in the presence of a condensing agent when necessary, preferably a basic condensation agent which comprises reacting the compounds when formal®ll. and III in which one of the symbols and Y2 represents a group The c - (* xi) ^ - ^ the Y and Y represents a reactive esterified hydroxy group, andV. whem.•which comprises reacting compounds of formulas II and III wherein one of Y and Y ^2 represents a group -0(Χ=^) ^ - ^ Υ and Y represents a mercapto group or a hydroxy group optionally etherified éthêrifié, e.g. with removal by distillation or distillation azêotrcpique hydrogen sulfide, mercaptan or alcohol released, and/or hot, for example at the boiling temperature. The basic condensation agents are the bases for securing the hydracid halogen released, e.g. mineral substrates such as 1' hydroxide, carbonate or bicarbonate of sodium potassium or calcium, or organic nitrogen bases, for example triethylamine or pyridine. Some of the starting compounds of formulas it and III are known. The novel compounds among those meeting the formulae II and III can be prepared by procedures analogous to those used for the preparation of starting materials known ';, and they also provide a obiet of the invention, as are methods for their preparation and use * Gh are prepared for example the compounds of the respective formulas II and III wherein Y ^ or HS represents a group - C. (the X * ^) ^ - therein by reacting a compound of formula 11 or III respectively wherein Y ^ or Y g and/or Yj represent hydrogen, in the usual manner, with a compound of formula Y, THE C ^ (- X-<1) - THEREIN,4 / (Ha) wherein the two symbols Y ' ^ each represent, independently of one another, a reactive esterified hydroxy group such as a halogen, a hydroxy group or mereaptoéthérifiêéthérifiê Υ ^, e.g. with phosgene, thiophosgene, ester or halogénothioformiquehalogênoforaique or halo-di-or chlorodithioformic a carbamoyl halide disubstituted nitrogen, e.g. by two lower alkyl groups. The compounds of formula III wherein HS and yj together form a group * c * x ^ may be obtained for example by reacting a compound of formula III wherein HS and Υ ^ represent 1 'hydrogen with a compound of formula Y' ^ - C. (the X ^ *) - (acre) therein wherein the two symbols The compounds of formula I can further be preparedness can " solvent borne coating from a compound of formula IV wherein Y ^ represents a group convertible to a group of formula - Κ ^0(Χ=^) - or a salt of such a group, converting the group Y ^ precisely in a group of the formula R ^ - C. (X-®^) - and, if desired, enConvertissant a compound obtained in accordance with the invention into another compound of the formula 1 and/or a free compound obtained in accordance with the invention into a salt or a salt obtained according to the invention in the free compound or another salt * The groups convertible to a group of the formula of Rj-C. (xi *) - are for example the groups which can be converted into a group of the formula R - () - the c ^ by solvolysis, it is say reaction with water (hydrolysis), hydrogen sulfide or a salt thereof or an alcohol (alcoholysis) or by reduction or oxidation. The salts of the compounds of formula IV are for example salts formed by acid addition such as hydrochlorides or sulfonates * The groups convertible by solvolysis in groups of formula Ε ^ -0(Χ=^) - are for example those meeting the formoles HS~(^ ^ the X) of c -, the R ^ ^ ^ - C. Y-HS) - or Y6THE C - (THEREIN?Ï8 ) -, in which and HS are each, independently of one another, " hydroxy esterified or etherified with a mono-alcohol or a mercapto group etherified with a monomercaptan, or represent in common etherified hydroxy groups by a diol or mercapto groups etherified by a mercaptan or a divalent cave irnino optionally state of salt and HS represents 1 to-pipérasino substituted in position 4 by a radical eliminable by solvolysis or Y ^ - Alk therein2 ^ - wherein Y is a group water xymé esterified or etherified with thy a the state or a Ni 2 a-hydroxy cyclic or a 2 - or 4 a-hydroxyfchioêther, or esterified with a carboxylic acid, or a group having a functional change carhoxv other than 1' esterification, and the sputtering satisfying formula (≈ 0) - -0 ^ Υ. An esterified hydroxy group is esterified hydroxy group such as a halogen or hydrogen halide by a carboxylic acid, among others a halogen such as chlorine or bromine, a lower alkanoyloxy group, for example acetoxy or pivaloyioxy, or an optionally substituted group henzoyloxy. An esterified hydroxy group by a monoalcohol is for example lower alkoxy such as ethoxy acetic acid or œéthoxy. Similarly, a mercapto group etherified with a mono-mercaptan is for example a lower alkylthio group, for example methylthio or ethylthio. Etherified hydroxy groups by a diol consist for example lower alkylene-methylenedioxy groups, e.g. ethylene-ethylenedioxy or propylene-methylenedioxy, and mercapto groups etherified by a mercaptan bivalent consist for example an alkyleneoxyalkylene dithiodisuccinic lower, among others ethylene-dithio or propylene-dithio-. The imino groups optionally in salt form are e.g. imino groups state-such as hydrochloride or halogénhydratesbroshydrate, state sulfonates, e.g. methane-suifonate or P-toluene, or state-salt mono sulfuric, for example methyl sulfate. The groups removable by solvolysis in position 4 of a group pipérasino are for example acyl groups derived from a carboxylic acid or a half ester of a mono-halide or carbonic acid such as a lower alkanoyl group, e.g. acêtyle or optionally substituted benzoyl, lower alkoxycarbonyl or beczyloxy - or phenyloxy-carbonyl or optionally substituted halo carbonyl. The hydroxymethyl groups are etherified by a silanol groups (lower alkyl) - sorting silyloxyméthyles - such as triméthylsilyloxyméthyle. Hydroxy etherified with a 2- cyclic hydroxy ether is for instance an group 2- tétrahydropyrannyloxyméthyle and by a 24 a-hydroxythioéther - or cyclic for example 2 a-tétrahydrothiopyrannyloxyméthyleor 4 a-dihydrothiopyrannyloxyméthy1 th. Un. ectérifiéhydroxycvtuyle group by an acid carboxyls unterstanding I-is for example a hydrexÿffiéthyle group esterified by an organic carboxylic acid or by a hemiester monohalide or carbonic acid, inter alia alcartoylcxyméthyle lower, e.g. CEA toxymathyle, optionally substituted benzoyloxymethyl, (lower alkoxy) - çarbcny1the XY-O-méthy, benzylexy - or optionally substituted phènoxy-to-carbonyloxyméthylearbony1oxyméthyie stylish or OCR. The S carboxy groups having a functional change other than an esterification and responsive th formula -0(=0) - Υ ^ preferably consist of cyano groups, optionally in salt form, e.g. state-halogénhydrates, methane - or P-toluene sulfonates or methyl sulfates, polyimino iœinoesters present in clusters or groups or orthoesters or orthoanhydrides, e.g. tri - (lower alkoxy) methyl - or trihalo -, for example the trichloro-methyl, or it may be a carboxy group anidéanhydrisé or, e.g. csrbanoyle halo carbonyl or optionally substituted. By hydrolysis of the groups specified, obtained for example, starting from. residues therein ^ - ^ de formulae Υ0(Υ γ, Υ ^) -, the R ^ - C. (^ Y-HS) Υ ^ - and - 0 - (≈ 0) groups of the formula - Η ^ 0 (=0) or from radicals of the formula - ^ Υ0(=00) - or HS-C. (YyYg) in which T? and HS represent éthérifiês mercapto groups, groups of the formula - (=O) - the c wherein R ^ represents a group 1' zino willwill pipera - unsubstituted in position 4 or a group R - alk-X ^ ^ ^ and R represents carboxy or hydroxyméthyle, and leaving groups - ^ ℮ Υ (≈ Χ ^) - in which Y is Y ^ - ^ - àlk-to-named xG and yq an iminoether or ortho ester group, groups of the formula R ^ - C. (=the X ^) - represents a group R wherein2" Alk-X2" - and R is an esterified carboxy group. The hydrolysis is carried out in the usual manner, for example in the presence of a hydrolyzing agent, when required in a water miscible organic solvent confectioneries, hot or at low temperatures, for example in 1' temperature range of O to 120C C., and/or in an inert gas atmosphere such as nitrogen. The hydrolysis agents are for example hydrolysis agents acids but when starting from compounds of formula iv in which Y represents a radical ^ 1-piperazino substituted h group or a group esterified hyiroxyméthÿle the noble éliainyirolysepar by a carboxylic acid or a carboxy-functional nodification. ^ Therein, can also be used basic hydrolysis agents. The hydrolysis agents acids are for example mineral acids such as hydrohalic halogens, for example hydrochloric acid, or. their acid salts, for example ammonium chloride, or sulfuric acid or the bisulfate, or carboxylic acids such as lower alcanoîques acids like acetic acid. The basic hydrolysis agents are e.g. hydroxides or carbonates of alkali metals or alkaline earth metals, for example 1' sodium, potassium or calcium, sodium carbonate or potassium. The water-miscible organic solvents are for example alcohols such as lower alkanols, such as methanol or ethanol, lower dialkylketones, for example acetone, cyclic ethers such as dioxane or tetrahydrofuran, dimethylsulfoxide or of the dimethylformani. FARs reaction with hydrogen sulfide or one of its salts, for example a metal sulfide or ammonium, inter alia the potassium sulfide, sodium or ammonium, for example it is converting groups of formula R ^ - C. (Yr, HS) into groups of formula R ^ - C. (AE)-. The reaction with hydrogen sulfide or a salt thereof is carried out in the usual manner, for example in a solvent and when required by. the presence of a catalyst or conventional condensing agent, by cooling or by heating, for example in the temperature range of 0 to 120* C., and/or in an inert gas atmosphere, for example nitrogen. The solvents are for example polar solvents such as water, alcohols such as methanol or ethanol, cyclic esters as the têtrahydrofuranr. th, the dinéthy1 formamide or dimethyl sulfoxide and mixtures thereof. By alcoholysis, can be converted for example groups of formula ΐ ^ - 0 (=Χ ^) - wherein Y g represents a group YC. - Alk-X2" and yq represents a carboxy group or a group H ydsnhydrisé ER xym e T-hr therein1th e comp IR relied on by a carboxylic acid, in groups of formula wherein R represents carboxy ester of ^! relied or hydroxymethyl. The alcoholysis is itself performed in the usual manner " for example in the presence of an acidic or basic and, when necessary, in a solvent, by cooling or by heating, for example in the temperature range of O to 12c °C about, and/or in an inert gas atmosphere. The acidic agents are for example mineral acids such as hydrochloric acid halides or halogens as broshydric acid, or sulfuric acid. The basic agents are for example alkali metal hydroxides as 1' sodium or potassium hydroxide, or. alcoholates of alkaline metals such as sodium or potassium alcoholate of the alcohol employed. The solvents are for example solvents miscible with 1' alcohol employed or an excess of the latter * The radicals therein ^ convertible by reduction to groups of the formula R ^ ^ ^ - C. the X) - feel for example those that respond confectioneries formula Υ ^ - σ (=Χ ^) - wherein Y ^ Q is OeUG-to-ale-to-named xG - or a group 1# - piperazine derivatives substituted by an alpha-phenol aralkyl - or alpha-araleoxycarbonyle such as benzyl or benzyloxycarbonyl. These radicals can be reduced to the radicals of the formula R ^ - C. (=the X ^) ^ - in which R is a group of formula - alk-X HOCH ^ - ^ 1-piperazino radical or an unsubstituted ' in position 4. The reduction is effected in the usual manner, when starting from compounds of formula XV in which Y represents a group of formula ^ 0=CF-alk-X2The c * - (e.g. ^} - by treatment with an alcohol, for example an alkanol or a cycloalkanol such as isopropanol or cyclohexanol, in the presence of a corresponding aluminum alcoholate, or by reaction with an alkali metal borohydride such as sodium borohydride or sodium cyanoborohydride, or with formic acid, and when starting from compounds of formula IV wherein Y represents Υ ^ ^0Ο - (≈ Χ ^) - and Y^0 represents a piperazino group substituted by an alpha-aralkyl or alpha-SCBA1fB in onycoxyca1i, by treatment with hydrogêne activated by a catalyst, for example hydrogen in the presence of a hydrogenation catalyst, a palladium catalyst among others, nickel or platinum, in particular palladium on carbon or nickel de Baney. Operations are carried out in the usual manner, for example in usually inert solvent such as an alcohol, for example an excess of the alcohol used as reducing agent, or a lower alkanol, when necessary by cooling or by heating, for example in the range of temperature to about -10 1o0 °C, when processing by 1' hydrogen, under pressure when required, for example in the range of pressure of about 1 to 20 bar and, when necessary, in a closed vessel and/or in an inert gas atmosphere. By oxidation, can be converted e.g. a group of formula 0The CK-Alk the X=2" C. (=X.1 ) in a group of the formula - ΗΟΟΟ - Α1Χ - Χ2^0(≈ Χ ^) -. Is used as oxidizing agents e.g. oxidizer compounds of heavy metals such as chromium-VI compounds, manganese-IV and manganese " seen, for example chromium trioxide, chronic acid or its salts, the manganese dioxide or potassium permanganate, or oxygen, in the presence of a solvent when required, e.g. water, a carboxylic acid such as acetic acid, a ketone such as acetone or mixtures of these solvents optionally containing water, by cooling or heating IIA, for example in the temperature range of -20 to +10C. °C about, in closed container and/or in an inert gas atmosphere such as nitrogen * In the reactions or oxidations mentioned deesus, the group forayle, in a compound of formula IV in which represents a group 0- HC~Alk X2" C. (=xx.j)~ may also be formed in situ, for example by oxidizing a hydroxymethyls group optionally esterified, for example a hydroxymethyl group optionally esterified by an acid halide or halogen carboxylic acid, for example from a hydroxymethyl group, chlorine - or bromine-aéthyle, (lower alkanoyl) or (lower alkoxy) oxyœéthyle - carbonyloxyméthyle or from a group forayle to functional change, for example a group acetalized fornyle, thioacétaliséacylalisé e.g. confectioneries or from groups of di - (lower alkoxy) - substituted di - or alkylene inférieurdioxyméthyle * (lower alkyl) - alkylthio - or lower alkylene " dithiodisuccinic, dichloromethyl or di - (lower alkanoyl) - oxymethyl, or released from a group optionally substituted ininométhyle, e.g. iminomethyl or aniloaéthyle, for example by hydrolysis * Thus for example, the compounds are obtained of formula IV wherein Y ^ represents a group of the formula HS-C. (the X ^ *) or Y ^ - C. (=the X ^) - by reacting a compound of formula HS~hr or Y ^ Q hr (IVB of) with a compound of formula or a compound of formula Ÿg c (=the X ^)~(SCI) or Hal-Υ,0-0(Χ .,) - Η1 ℮ (IV) in which Hal represents a halogen such as chlorine, with a compound of formula preferably as indicated for the reactions of compounds of formulae II and III. In this example the compounds of formula X-Y wherein Y represents a group R ^ ^ - ^ YCC HS) Υ ^ - - or0(1^ ^ Υ) by condensing a compound of the formula first IYd or entering Britain respectively, in the usual manner, with a derivative of the acid of the formula H-c-orthoforaique (^ ^ Y-Y-HS) (abortion) and then with a compound of formula ïVf. The compounds of formula I can still be cyclizing a compound of formula The R ^~C.."~pH at the NH ^ ^ ΚΒ - Υ VK chain (THEREIN) wherein one of the symbols and Y ^ - represents a group of formula0(6^ ^ Υ) ^ - Κ éliairable both a group and is oxo to optional functional change, uu a salt of such a compound and, if desired, converting a compound obtained in accordance with the present invention superimposed into another compound die, and/or formula X by converting a resulting free compound conforspent to 1' ℮η disclosure. a salt or salt obtained according to 1' invention in the free compound or another salt. The groups éliminabl Associates. in question are for example groups of formula -0(≈ Υ ^ L-' hydrogen, acyl groups or sulfo attached on the thio group X ^, and optionally in the form of salts. The acyl groups are in particular those which fall within the formula K ^ -0(=0) -. An oxo group to functional change is for example a thioxo group or iœino. The salts of the compounds of formula V are for example the salts formed by acid addition, halogénhydrates such as, for example the hydrochlorides, or alkali metal salts of the compounds of formula V wherein - Xi - The cyclization is carried out in the usual manner, when required by the presence of a condensing agent and/or a solvent and when necessary eèt also cooling or heating, for example in a temperature range of 0 to 130 * 0 about, in a closed vessel and/or in an inert gas atmosphere such as nitrogen. The condensation agents are for example condensation agents acidic or basic. The condensation agents acids whose use is indicated particularly when starting from compounds of formula V wherein represents an acyl group, are for example mineral acids or their acid salts and acid anhydrides, for example halo such as hydrochloric acid, sulfuric acid or the bisulfate, for example the potassium or ammonium bisulfate, phosphoric acid or its acid anhydride as acid polyphosphoriqueï boric acid, sulfonic acids such as p-toluene-sulfonic acid or Lewis acids such as boron trifluoride or antimony pentachloride. Instead operate in the presence of a condensing agent acid, can also be from compound cyclising state acid salt. The basic condensation agents are for example alkali metal hydroxides. or earth as 1' sodium, potassium or calcium, alkali metal carbonates such as sodium carbonate or potassium, or organic bases -2- θ nitrogen, preferably tertiary amines coace ls pyridine or the trialkylarînes. as the triithyinferseures 1 and healthy. Instead of operating in the presence of a base.* can also be from a compound of formula ' V wherein - X-Y-- ^, ^ represents a. hydroxy or nercapto state of alkali metal salt " solvents are e.g. aromatic or araliphatic hydrocarbons stoneware the: benzene, toluene, xylenes, hydrocarbons halogens as di -, tri - and tetra-chloromethane, aliphatic or cyclic ethers such as ethyl ether, dioxane, the tetrahydrofuranre, the diméthylforïcamide or dimethyl sulfoxide, and also water and aqueous solvents of the type mentioned above, . The starting compounds of formula V which are novel and can be prepared by procedures analogous to those used for known products. Thus for example is - obtains the compounds of formula V wherein represents a group of formula - C. (Υ - ^ and Y^2 also represents hydrogen or a group of the formula -0 (Υ=^ by reacting a compound of formula VA The R ", the KH - C. - - pH value (will) with a compound of formula Z-C(vi ^) - hi (and VB) wherein Z represents a hydroxy group or an oxo group and Z is hydroxy etherified ^ and Y is oxo or inino or The compounds of formula will serve as produced starting can be obtained for example from the d * a compound corresponding nitrated (containing a nitro group in place of NHg -) or a corresponding disulfide (containing the group - S-s-pH value (k02) - NH-c (=X.the n ) - it, in place of - the X ^ hr) by reducing the nitro groups and optionally the disulfide bridge, by example by reaction with hydrogen in the presence of a catalyst of a HYdrogénation, for example palladium on carbon, with metals or metal compounds reducing, by such as iron, zinc, tin, or stannous chloride or, for redecrease of a disulfide bridge, with the borohydride na and, for the reduction of the nitro group, borohydride na a sulfone. The compounds of formula V wherein reprépréparés for example from a compound of formula perceives hydrogen and Y12 a group - C. (* thereinthe n j) - the R ^ may be , RT OF THE KH (Ve) by reaction with a compound of formula Z-C(* ^ therein (and VB) which-' Z-.-represents " a group '. cmlMen - ^ represented a group. Yïÿdrexy-to-eihérifié. and T. and one-oxo group or Z and ' - the j ^ therein. - the fermentIsaconsun. the 4;Xletain or: The j-O-vUUvVtJlAA '|/" 1. ti - " \ e in tan e "them" for the admission ïes-to-UQEosêsfdreûle ^ / of VB is, is. - operates as described above. , / -. In ES - I->XorœuleYcnécessaires compounds of this purpose as■product S dedépartpêuvenî be - prepared by - for example; from mxomposé of forsatle ;. ;. '. in 1 is equelprotè Ge the group X ^ hr, by. example, by bensylatioacàrbpbensoxylation * ^ ^ d-oxidation or a coêïnosémerêaptan type (the X ^ hr " shush) disulfide, then nitrated and releasing *10^ - hr - group X, for example by reduction.■ The compounds of formula Y in 1 ague11 " represents.' a group - of iorEUle - C (^) - the K ^, 3^ representsa tnio bridge - and Y^2 a group sul.fo optionally step d " T-salt.., . can further be prepared, by conversion. of * compound.' i-: - *! :.; manner 'usual, by reaction with, a tMosulf' reporting, the - sodium thiosulfate, in the dye salt:: (1 8 1 ΐ όΒ ηΐ ℮·Υΐ > Η·, - ^ - ^ 2 Χ Υ * ^ ^ U-oïi fact then, reacting as: indicated above with a compound of formula with Yb " and for example, in a compound of formula I plex wherein R represents a group - ^ the rg alk named xG - and Rg is esterified carboxy, may be hydrolyzed with the latter in the usual manner carboxy group, for example in the presence of an acid or basic agent, when required by the presence of a solvent, under cooling or heating in re * - for example in the temperature range of 0 to 120®C. - and/or in an inert gas atmosphere such that nitrogen. The agents are acids by hydrolysis g. protonic acids such as mineral acids, by example hydrochloric acid or hydrobromic acid, acid sulfudecoding apparatus or phosphoric acid, organic acids ifrOIgene products, e.g. acid-toluene-sulfonic acid or acids carboxylic, . for example acetic acid and other acids lower alkanoic acids. The hydrolysis agents the basic groups for example metal hydroxides or ammonium, by example alkali metal hydroxides, alkaline earth or LFDArelief, among others 1' sodium hydroxide, potassium, calcium or ammonium, or alkaline metal carbonates, e.g. potassium carbonate or sodium, or alternatively organic bases such as tertiary amines, e.g. triethylamine. The solvents are in particular the water-miscible solvents such as lower alkanols, such as methanol or ethanol, ethers or ketones miscible th water as a dioxane, tetrahydrofuran or acetone, the diméthylforma&structu or the diméthylsulfoxyda * One may further oxidize water groupsthe rg xyméthyles in carboxy groups. The oxidation may be conducted myof voice known per se, for example by reaction with a compound of heavy metal having oxidative properties, leaving of the preferably hydroxymethyl group by an oxidizing compound coutenant chromium-VI or manganese-VII.* e.g. trioxide chromium or more preferably potassium permanganate, or by a manganese-containing compound~IV as the dioxide of manganese. It is carried out preferably in the presence of a solvent or suitable diluent, for example acetone or pyridine derivatives, or a mixture of these solvents, preferably aqueous, when i. necessary by cooling or warming, by example in a temperature range of 0 to about 80 °c. in ν .also, the obtained compounds. -: wherein - X-:the X nts -.. - ·. · / - ■by processing through the suitable agents for the * D. 11- oxydatiens, can be 1' phénylalkyler alkylating or by reaction with a reactive ester of a lower alkanol or phenylalkanol YR. wetted the optionally substituted as indicated above, or may be substituted by a lower alkyl group,, lower phenylalkyl, lower alkanoyl or lower alcoxyearbonyleparréaction with an anhydride or an acid chloride or a lower alkanoic halogénocarbonate D.1 lower alkyl unsubstituted piperazino group * üe -4 position can be substituted to L ' nitrogen by lower alkyl e.g.■reactive ester by reaction with a TM of aicanol lower, and the pipe razino group optionally having a lower allele group at position 4 can be ii-to-oxycèé confectioneries by treating 1 * 81 of an agent s-oxidation * - In this regard, the reactive esters are especially the Leu esters of inorganic acids, for example hydrochloric esters ., broiabydrioue. s or iodhydriques, or sulfuric esters * but also esters of sulfonic acids, such as fluorosulfonic acid or organic sulfonic acids such as p-toluenesulfonates. The reaction avecavec.les reactive esters or with anhydrides or acid chlorides is effected, in the usual manner * e.g.; establishing presence * iuj basic condensation agent such as the natural ' a hydroxide or an alkali metal carbonate, for example 1'sodium hydroxide or potassium or sodium carbonate or potassium, the d * a * by alcoholates exempled' an alkali metal lower alkoxide such as. the sodium methylate the of ., or sodium hydride, in an inert solvent/HU advantageously, for example in the dimethylfonsamide or K-mèthylpyrroïidone. . The agents which are suitable for K-oxydatiOa are b for example. ".' compounds peroxides such as hydrogen peroxide, organic hydroperoxides as 1' hydroperoxide. tert. butyl, organic peracids, for example aromatic or aliphatic acid * rcarboxy PEs1ieues as 1* m-ehloroperbenzoïq'ue, peroxyacetic acid or acid sojïoperphtaliqueT- heavy metal compounds having oxidative properties " for example compounds of the chromium-VI or manganese-IV or manganese-VII as chromium trioxide, chromic acid, manganese dioxide or potassium permanganate, mineral acids oxygenated oxidizers such as nitrogen oxygen acids, ' halogens or chalcogens, anhydrides or salts, for example nitric acid, the peroxide. nitrogen, selenium dioxide or sodium metaperiodate, as well as ozone. The solvents examples of suitable hydrocarbons halogens such as halo-alkanes, by such as carbon tetrachloride, chloroform or methylene chloride, or carboxylic acids, e.g. alkanoic acids, among other acetic acid, and anhydrides thereof. In a preferred embodiment of the oxidation process, it is possible for example to oxidize nitrogen compounds of formula I wherein X ^ represents an imino group or represents a group 1- piperazino group optionally substituted by a lower alkyl group in position 4, and one of the residues and/or carries an unsubstituted ring nitrogen atom, by reaction with an organic peracid, e.g. m-chloroperbenzoîque, in a haloalkane such as chloroform. Conversely, in the compounds of formula I wherein represents an imino group oxidized to nitrogen and/or represents a group 1- piperazino oxidized to nitrogen and optionally substituted lower alkyl, can be reduced or oxidized ring nitrogen atoms. The reduction, is carried out using conventional reducing agents, e.g. nascent hydrogen or hydrogen activated by a catalyst, among others iron or zinc and an acid such as 1' hydrochloric acid, or hydrogen in the presence of Raney nickel, preferably in an inert solvent such as a lower alkanol, or else with a phosphorus compound III-such as a phosphine, for example triphenylphosphine or tri-n-selenide, or a phosphorous ester, e.g. a phosphite of triabodies Ikyle lower ., between - other lephosphite ...■of thy a the iridescent or triethyl. The compounds of formula ii obtained th free state, and are capable of forcing salts can be converted into 5 salts in a manner known per se. Acids for example with the aid of a base or d'acid salt capbcxylique suitable and bases using a mineral acid, usually in the presence of a solvent or diluent. Salts obtained can be converted so 10 in the known free compounds, e.g. by treatment with an acidic reagent such or ' a mineral acid * The compounds, including salts, can be obtained its hydrates or containing occluded condition of the solvent used for the crystallization. I5 because of the close relationship between the novel compounds in the free state and in the form of salts, when, * in all of the above and in all that follows, this is referred to as free compounds or salts thereof, that is said should be included if necessary like s1 applying respectively to 0! salts and compounds corresponding free. The invention also includes embodiments of the method in which the starting point is a compound obtained as an intermediate in a process step is carried out and any stages a missing, or 5 well forming a starting material in the reaction conditions or is used a starting compound state of derivative, optionally âl ' éfcat salt. In the method according to the invention, are preferentially used starting materials which lead to the compounds de - D. crits as particularly interesting en introducing novel starting * imposition products and methods for their preparation are also an object of the invention. The novel compounds have advantageous pesticidal activities, in particular to the related 5 parasitic helminths. Very well tolerated, e.g. the d * experience # animals such as mice, Saccostomus Xanthomonas campestris, rats, hamster, Kerionesunguiculatus, dogs, monkeys or hens, they have the # trematodes' such - that the fssciolidés, e.g. of Fasciola hepatica, and firstly on schistosomes, e.g. of Schistosoma mansoni, a Schistosoma japonic extracts a-URNs and a Schistosoma haematobium, and against the causes of filariasis, e.g. Setaria viteaeLitonosoides and Pneumocystis. E.g. to thereby, the compounds used for the treatment of hamster suffering old of 6 to 6 weeks Schistosoma mansoni, PO in a single administration (for example using a gastric tube) exhibit of The experimental procedure below was for example highlighting antischistosoaique activity of compounds of formula I on the mouse white and the Syrian hamster 9.ï It has infected mice weighing 20 adult white Was then verified spurious adult # by the "miracidia of to-Biologist-testing". the test animals have been arbitrarily distributed in groups of 10 individuals each, two groups for control groups. The other groups were treated with at least 3 individual doses progressive compounds being tested. Simultaneously, a control group of animals were sacrificed and necropsied, for determining the average number of worms at the start of phase * observation , -14 furnaces '., after provides em-have, - bone' determines each 'week the number of viable eggs deposited, to L'/due to using "the n The m: raeidia-to-hetchin ^ T-&7th.: "" β weeks, after. treatment, all animals were sacrificed including those of grouped unsupplemented control 5 treated and were found to be necropsied. For each animal, was counted the total number of schistosomes discovered " it has been determined the ratio of the average number of worms of each treated group at average number for both controls and calculated the value of villein, (reduction 50 * Ked For the determination of the activity of antifilaire ' coBtposés of formula 1, was operated as described below using as test animals ïieriones (hr, ungulculatus) 15 and rats (Kastomys heteromorpha). It has infected young adult Meriorneskastomys and randomly different chicken flocks, weighing V-TO-.C. 3ΰ. - - - ℮ ' 50 gm, by bites of ticks from the species Bdellonyssus bacoti according to the procedure of F. NISER and P. Swell (military should * © Hyg " Yi, 2 - 5 δ 296 (1948). the containers of infection have; been held in continuous flow: each Monday for example, the •" tiquee therein have. been infected by Pneumocystis Litomosoides stage ": - _v.; - v-' lervairs.; - and are left off eating during 8 the hours. blood, peripheral rodent various carriers numerous micro-5 wired. Thursday non-infected rodents have been held, during 8 hours in the containers in which they were bitten by ticks freshly hatched but primarily is directed to of 9 has 10 weeks, adult parasites is searched by examining samples of 5 ^ mm in the circulatory blood capillary wherein the microwire * circulate the blood samples to which, adds 1' heparin are dis -1; microscopic gives of the mined 100 times *, counted the number microfilariae living in 15 fields 1.8 mm diameter * for the other assays, using only animals carrying more than 50 microwire "these animals are arbitrarily distributed into groups and individual held" Macroion centeredly in cages. The groups of 5 animals each are processed by multiple oral doses substances 5 days examined during successive. A group is the control group untreated * The same day after treatment, the mierefilaires are counted exactly the same as before treatment. These accounts are periodically performed 2, 4 and 6 weeks after treatment. Determining a total number of microwire live and dead cell carried by each animal. The minimum dose effective (EMD) on the microwire is the dose which, 5 days after treatment, has caused a decrease of at least 95 % the number of microfilariae in the circulating blood. This dose is typically verified in a second series of experiments. The minimum dose curatively (25 DHC) on the microwire is the dose which has destroyed all the microwire in all animals treated during 6 weeks observation - after - treatment (HPC Sfcriebel, in vivo. NN.Y. CDAA. IBS. 160, 491 - 498, 1978). For some materials slow acting, the period is increased to 8 weeks. Parallel to the repeat experiments for the determination of the induced, RN also determines the DKC in second. Was used as other pests experience inter alia Dipetaloneœaviteae " carried in the same species of rodents that Litomosoides Pneumocystis. Soft ticks (Oraithodoruamoubata) have served as an intermediate hosts and, after supplying the infective by blood, they have been maintained at a temperature of 28 °c and relative humidity ?0 to 80 M heteromorpha and H. unguiculatus were then infected with 70 larvae per animal, by subcutaneous injection dAA " * the neck. 11 to 13 weeks after infection, we investigated the microfilariose in animals as for L Pneumocystis. Furnace experiments, was used only animals containing at least 50 microwire by 10^mm in blood. To avoid as much as possible the risk of d - * a "shock" - therapeutic1 ** has not been used of animals infected. since the days - 1$weeks. The results performed in those assays and in d * other tests have shown that the compounds of formula 1 offered excellent the micro - and macro - filaricides, for example to the related lymphatic filariasis®onchoceroses and, as well as excellent schistosomicides, the dosage indicated in coma * effectiveness is about 3 to 15 milligrams/kg per day in oral administration during 5, 0 bear " Pharmaceutical compositions of the invention containing S. compounds of formula I or their salts acceptable # for I ' pharmaceutical use are compositions for enteral, for example oral or rectal, and parenteral & individuals warm-blooded, compositions that contain the pharmacological active substance alone or with an appropriate pharmaceutical vehicle * the dosage of the active ingredient depends on the species of warm-blooded individual, its age and condition of the individual, as well as the mode of1administering. Without a normal case, for an individual weighing about 75 kilograms, and in oral administration, one can estimate the approximate daily dosage to about 0, 25 confectioneries 2.5 gm " preferably in more equal doses. The pharmaceutical compositions of the invention contain for example about 10 preferably about 80 to 20 to 60 of the active substance. The pharmaceutical compositions according to the invention for 1' enteral or parenteral administration are for example in the form of dosage units such # that of pills, tablets, capsules or suppository # ** bulbs or the compositions are prepared in a manner known per se * for example by conventional mixing, granulation, of drageifieation, dissolving or lyophilizing * thus, obtainable pharmaceutical compositions for oral administration by combining the active compound with solid vehicles, making the mixture optionally & pelletised and then forming the mixture or the granulate # state of tablets or dragee cores #, after adding suitable auxiliaries if desired © U-if so required. The vehicles who are suitable in particular are fillers such as sugars, for example lactose, sucrose, mannitol or sorbitol, cellulose and/or are derived from calcium phosphates, e.g. tricalcium phosphate or calcium acid phosphate, binders such as starch paste obtained e.g. from corn starch, wheat, rice or potato starch, gelatin, tragacanth, methylcellulose and/or polyvinylpyrrolidone and/or, if desired, désagrégéants agents such as starches mentioned above, as well as carboxymethyl starch, cross-linked polyvinylpyrrolidone, agar, alginic acid or its salts, for example 1' sodium alginate. The auxiliaries are primarily die process products for lubricating and smooth the flow, e.g. silica, talc, stearic acid1 or its salts, for example magnesium stearate or calcium, and/or the polyéthylêne glycol. Dragee cores, suitable coatings are applied, optionally gastric resistant, and can be used for this purpose inter alia of sugar syrups and concentrates may contain gum arabic, talc, polyvinylpyrrolidone, polyethylene glycol and/or titanium dioxide, gums solutions in suitable organic solvents or mixtures of solvents, or, when it is desired gastric juice-resistant coatings, solutions of suitable cellulose derivatives such as cellulose acetate phthalate'd * or hydroxypropylmethylcellulose phthalate. To tablets or dragee coatings, can be added dyes or pigments for example for identification or characterization of different doses of active ingredient. As other pharmaceutical compositions for oral administration, include capsules gelatin as well as soft sealed capsules made of gelatin and plasticizer such as glycerol or sorbitol. The capsules may contain the active substance in the form of granules, for example in admixture with fillers such as lactose, binders such as starches and/or lubricants such as talc or magnesium stearate, and possibly stabilizing. Mainly in soft capsules, the active ingredient is preferably dissolved or suspended in suitable liquids such as oils, fats, "1' - - oiled paraffin or polyethylene glycol e liquid and stabilizers may also be added. " The incorpora itiens pharmaceutical for 14 rectal administration are suppositories parexemple consisting of a combination of the active compound with a mass base for suppositories. The mass base for suppositories may for example natural or synthetic triglycerides, hydrocarbons parafriniques " polyéthylêne glycols or higher alkanols. May also be used gelatin rectal capsules: containing a combination of the active compound with a base mass; the components of the base mass are for example liquid triglycerides " polyethylene glycols or For parenteral administration, preferred are primarily aqueous solutions of an active substance herself state water soluble, for example to the state of water-soluble salt, or suspensions of the active substance, for example oily suspensions for infections "is prepared using a solvent or lipophilic vehicle suitable, for example a fatty oil such as sesame oil, or synthetic ester of fatty acid, for example ethyl oleate, or a triglyceride, or aqueous suspensions for infections containing thickener" such as sodium carboxymethylcellulose, sorbitol and/or dextran hydrogels and optionally further contain stabilizers. The dyes or lotions are in most cases based hydro-ethanolic " containing inter alia polyalcohols, for example glycerol, glycols and/or polyethylene glycol as humectants which reduces evaporation, and superfatting agents such as fatty acid esters and die '. lower polyethylene glycols, it is i.e. lipophilic substances soluble in the aqueous mixture and which serve to replace the fatty substances removed by the alcohol and, when cF. is necessary, other auxiliary agents and additives. The invention also includes the use of compounds of formulae I and II and salts of these compound capable of forming salts for combating advantageously helminths parasitized-ires, primarily those which belong to the families mentioned above is checked, the following examples illustrate the invention without however limiting same; - in these examples, the indications of portions and Is dissolved? 0 grams (0.28 moles) of 2 a-tert. butyl -6- isooctyl thiocyano or-benzothiazole derivatives in 1200 ml of ether and added dropwise, with stirring, 33 grams (0.33 moles) of 4 a-méthyIpipératine. The mixture is stirred for 1 hour, filtered and washed first with ether and petroleum ether. The obtained 2 tert-" - butyl-6- [(4-me T-of HY 1 the Ra - Zi are n-th P-PEI -1 - therein 1 ) - t-H-I-O-arbonylamino]-benzthiazole melting 176-177°C " Can be prepared in an analogous manner the compounds SUI provides -. vauts; 2- ^ - l-tert.-goal5- methoxy -6- [(4-methylpiperazine-1 yl) - thiocarbonylbis-to-aœino]-benzthiazole, melts at 150 and 15' 1°. 2 a-tert. butyl-5-chloro 6 - [ (4-methylpiperazine-1 ""-yl) - thiocarb<myl amino]-benzthiazole, melts at 156-160*0, and 2 tert ~méthyl 5 and 6 - [(4 a-mêthylpipérazine-to-1 yl) - thioearbonyl~] an amino-benzothiazole derivatives, melts at 185 - 18? the c *. Example 2 4.33 Grams is dissolved (0,183 moles) of sodium in nitrogen atmosphere in 300 AI of ethanol. Added 1?, 6 grams (0,094 moles) of n-oxide dihydrochloride of the n-methylpiperazine. 15 minutes later, filtering the sodium chloride formed is rinsed to ethanol. Is added dropwise to the filtrate, at room temperature, to a suspension of 24 grams (0,085 moles) of 2 a-terttert.butyl -6the O ->isothiocyai -5- 'in' methyl-benzothiazole derivatives 120 ml of ethanol. Then agitated during 2 hours then distilling ethanol under vacuum. The residue is extracted by water and methylene chloride. Phase is separated off (100 ml) methylene chloride * it is dried on sodium sulfate, filtered, diluted by 100 ml of petroleum ether and " is cooled to 0 °c. After filtration, the obtained 2 a-tert. butyl-5-methyl 6 - [(4 a-néthyl-a 4 a-Qxydo and 5 - piperazine1- ylbenzoyl) thiocarbonylamino]-benzthiazole - 129 - 131 °c melts. Can be prepared in an analogous manner the following compounds: ' 2 a-tert.-to-butyï-to-5-methoxy-6 - [(4 methyl-4 pyridinyl-piperazine 1 yl) -0 thiocarbonylamino]-benzthiazole, melts at 144 °c, 2 a-tert,-butyl 5 a-chlorc>- 6 - [(4 methyl-4 pyridinyl-piperazine 1 yl) thiocarbonylamino} - benzothiazoln melts at 119 - 121 *. Example 3 the I * is dissolved 21 gm (C., 0? 6 moles) of 2 a-tert. butyl -6- 5 or isothiocyano -5- methoxy-benzothiazole derivatives in 400 ml of acetone are added dropwise to a solution of 12 gm (0,092 moles) of n - (2 hydroxyethyl) - piperazine in 40 ml of acetone. The mixture is stirred for 2 hours, cooled to 0 °c, filtered and washed with acetone and then with ether and finally ether - EP 1 trole. The obtained 2 -1ert.-to-buty1-to-5-methoxy -6^ - [4 - (2 hydroxy - , ethyl) - piperazine -1- ylbenzoyl] a-thiocarbonylamino ^ - benzthiazole melts at 161 - 162 * 0. Can be prepared in an analogous manner the following compounds *. Example 4 ' 27 Is dissolved, 8 grams (0.10 moles) of 2 a-tert.-to-buty1 and 6 thereof or isothiocyano -5- methoxy-benzothiazole derivatives in 150 ml of dimethylformamide and added 14 grams (0.13 moles) acid 3-mercapto-- ' propionic. The solution is stirred in nitrogen atmosphere during 2 hours at room temperature, is cast on 2 kg of ice and stirred juBqu ' to solidification of the product. Is filtered, washed with water and heated in 700 ml toluene, water is removed by decanting, dried on sodium sulfate, clarified with active charcoal and filtered. The filtrate is diluted to about 30 - 40 * 0 perse 700 ml ether petiole is cooled slowly to and 5 °c. Is filtered off and washed with petroleum ether. Obtained n - [2 a-tert. butyl 5 A-Eiéthoxy Ben~ - zothiazole6--yl] - dithiocarbamate - O (2-ACrboxyethyl) melts at 154 - 156®C.. Can be prepared in an analogous manner the following ii composed N [2 tert-. a butyl - - benzothiazôle~6- ylbenzoyl] dithiocarbamate of s - (2-carboxyethyl), melts at 135-137° W, n [2 a-tert.-to-buty1-to-5 chloro-specific materials- zothiazole&6- ylbenzoyl] stage of said hiocarbaa&Te of O - (2-carboxyethyl), melts at 95 - 9? °C, and n-[2 a-tert.-to-buty1-to-5-me the Thyl-benzthiazole -6- s-yl] a-dithiocarbaaate - (2-carboxyethyl), melts at 155 - 158 degrees. Example 5 By operating comae described in examples 1 to 4, can be further prepare the following compounds: THE N - [ 2- ter. - bütyl -5- methoxy Benz0thiazol -6~-yl]~dithioearbaiûafce of s - (2 a-carboxypropyl), melts at 136 and 140 °, n [2 a-tert. butyl-5-methoxy-benzothiazole derivatives thereof 6 yl] a-dithiocarbaBate s-carboxymêthyle, 231 - 255®C. based confectioneries, the K - [2- tert.-to-buty1-5- - methoxy-benzothiazole derivatives6- ylbenzoyl] a-thiocarbamate-OD - (2-carboxyethyl), melts at 173 and 176°. Example 6 By operating as described in examples 1 to 4 or according to a preparation process described herein for compounds of formula I -, can be further prepare the following compounds: THE N - [2- tert. butyl-5 a-oéthoxy-benzthiazole -6- o - ylJ-to-thiocarbamate (2 a-carboxylthyle), melts at 231 - 233 °c, 2 a-tert. butyl -5- methoxy -6- [(4-methylpiperazine-1 yl) - carbonyl-amino-]-benzthiazole~, melts at 1? 6 - 179*0, 2 tert-buty - *1-5the Thyl - - mth6- [(4-me thylpipé the Ra - zine derivatives1- therein1) - thiocarbo-to-nylaminoj-benzoxazol, 195 - 197®C. melting, 2 tert-. - butyl 5-chloro--6- [(4 a-cethylpiperazine-to-1 yl) - thiocarbonylamino] a-benz.oxa2ol ., melting^0 181 - 162, 2-tertiarybutyl - ^ - methoxy -6- [(4 A-Eethylpiperazine-to-1 yl)~] fchiocarboaylamino-benzoxazol, 2 tert-. - butyl 5 a-methylthiobutyric acid and 6 - [(4-methylpiperazine-1 yl) - thiourea~] carbonylamino--benzoxazol, 2 a-tert. butyl -6- [( - 4-me thylpipérazine1- ylbenzoyl) - thiocarbonylamino] benzoxazble, * - 2 tert-butyl 5-methyl 6 - [(4 a-mêthy1-to-4 pyridinyl-pipe razine L-y1) thiocarbonylamino]-benzoxazol, based confectioneries 141 - 143®C., 2 a-tert. butyl-5-chloro 6 - [(4 methyl-4 pyridinyl-piperazine 1 yl) thiocarbonylamino]-benzoxazol , melts at 135 - 137*0. 2 a-tert. butyl-5-methoxy-6 - [(4-me the Thyl-to-4-oxido-piperazinyl-1 yl) thiocarbonylamino]-benzoxazol " 2 a-tert. butyl-5 a-néthylthio and 6 - [(4 methyl-4 a-oxyd ο - ρ PEI raζine-a 1 a-yDthiocarbonylamino]-benzoxazol, 2 a-tert. butyl -6- [(4 methyl-4 pyridinyl-piperazine 1 yl) -] thiocarbonylaaino-benzoxazol, the K - [2- tert. butyl -5- π ℮ thy a1the benzoxazole - -6- ylbenzoyl] dithiocarbamate of s - (2-carboxyethyl)" melts at 160 - 163 °c, n [2 a-tert. butyl-5 a-chlorobenzoxazole-to-6 yl] a-dithiocarbaaate s - (2-c rboxyéthyle)" melts at - 85. 88®C., N [2 tert-. - butyl 5-methoxy-benzoxazol-to-6 yl] dithiocarbamate die e - (2-carboxyethyl)" THE H - [ 2- ter. a butyl - - 5- methylthio-Bas zoxa - zole derivatives6- y-L-] - dl MC iocarbamate of s - (2-carboxyethyl), 2 a-tert. butyl-6-nitrate 5 - [(4-methylpiperazine -1- ylbenzoyl) - thiocarbonylamino] benzoxazol - " 2- ter. - butyl 5 a-c (4 a-mëthylpipérazine d-yl) - thiocarbonylamino] benzoxazole derivatives, 2 a-tert. butyl-6-nitrate 5 - [ (2-me the Thyl-to-4-oxido - pipe the Ra zine derivatives-1 - ÿl) thiocarbonylaninoj-to-benzoxaeole, 2 tert-. butyl 5 - " [(4 a-méthylp azine groups R-PEI -1 - therein 1 ) - t-H-I-O-arbonylaaino] benzoxazole derivatives, THE H - [2- ter. a butyl - -6the nitro-benzoxazol - -5--yl} - dithioearbamate of s - (2-carboxyethyl), hr - [2- tert. butyl-benzoxazol -5- ylbenzoyl] dithiocarbamate of Β - (2- carboxyethyl), _ jj.p 2 a-tert. butyl-5 a-ffiéthoxy and 6 - [ {4 -&éthyipipérazine-to-1 yl) - alkenylthio "] carbonylamino--benzimidazole derivatives, 2 tert-. - butyl 1 - ethoxycarbonyl-therein - * - séthoxy6- [(4 a-méthylpipératine " 1- ylbenzoyl) - thioçarbonylamino] - benzimidazole derivatives, 2 tert-. - butyl 1 - dimêthylcarbamoyl-a 5 a-oéthoxy -6- [(4-me thy a lpipérazine -1--yl} - thiocarbonylanino] a-benzinidazole, 2 - tert. butyl-1 newborn thanesulfonyl-a 5 a-oéthoicy and 6 - [(4-me thylpipérazine -1- ylbenzoyl) -] thiocarbonylaaino-benzimidazole derivatives, 2 - - tert. butyl1- thy a mth1-5thoxy - mth- 6 - [(4-me thy a Z-bly lpipé the Ra -1- ylbenzoyl) thioearbonylaminoJ-benzimidazole derivatives, 2 a-tert. butyl-1 benzyl-5-methoxy-6 - [ (4 a-oéthylpipérazine-to-1 yl) thiocarbonylamino} - benzinid8zole derivatives, 2 tert-. aim - yl 5 a-CHL and gold-O -6- [(4 - " ethylpiperazin-to-1 yl) - thiocarbonylamino]-benzimidazole derivatives, 2 a-tert. butyl-1 a-éthoxycarbony1-to-5-chloro 6 - [(4-me thylpipérazine -1- ylbenzoyl) - thiocarbonylamino]-benzimidazole derivatives, 2 - tert. butyl-1 a-diméthylcarbasoyl-to-5-chloro 6 - [(4-me thylpipérazine -1- ylbenzoyl) -] thiocarbonylamine-benzimidazole derivatives, 2 a-feert.-butyl 1 a-méthanesuifonyl-to-5-chloro 6 - [(4-methylpiperazine-1-yl) - $thiocarbonylamino]-benzimidazole derivatives 2 tert-. - butyl 1-methyl 5-chloro 6 - [(4-me thylpipéraziBe l-yl)" thiocarbonylamino]-benzimidazole derivatives, 2- tert. butyl -1- ylbenzyl -5- chlor -6- [(4 born hylpipérazin - T-I1- ylbenzoyl)] thioçarbonylamino-benzimidazole derivatives, 2 tert-*. a butyl - -6- [(4-me T-LP-PEI RAZs of HY unequal-a 1 - therein 1 ) - mC CAI arbonylamino} benzimidazol, 2 tert-. - butyl 1-ethoxycarbonyl -6~[(4-me thy a lpipérazine-a 1"-yl) thiocarbonylamino]-benzimidazole derivatives, 2 a-tert. butyl -1- dimétbylcerbamoy1 -6- [(4 a-méthylpipérazine-to-1 yl)] thioçarbonylamino-benzimidazole derivatives, 2 a-tert. butyl * - 1 a-méthanesulfony16- [( - 4 a-mêthylpipérazine1the Y1 -)] thioçarbonylamino-benzimidazole derivatives, 2 a-tert. butyl -1- ffiéthyl -6- [(4 a-méfchylpipérazine-to-1 yl)~] thiocarbonylamino-benzimidazole derivatives, 2-tert.-to-buty1-1- ylbenzyl -6- [(4-methylpiperazine-1 yl) - thioc&rbonyXamino] Ben zimidazole, 2 a-tert. butyl-5 a-propyltbio and 6 - [(4-me T-of HY lpipérazine -1- therein1) thiocarbonylamino]-benzimidazol -, 2 a-tert.-to-bütyl I-ethoxycarbonyl-5 a-propylthio and 6 - [(4 a-methylpiperazin e 'l Y 1 ) - cAI arbô ny is the Tb 1 aÒ innocent] Ben 2 da are bound OS 1 i, 2 tert-. - buty1- i-die process&thylcarbanoyl-to-5-pick>pylthic and 6 - [(4 a-œéthyl-piperazine-I-yl) lamino]-benzimidazol - thiocarbony, 52- tert. butyl-dl-methanesulfonyl -5- propylthio -6- [( - 4 a-methyl.pipêrasine1- ylbenzoyl) - thiocarbonylamino] - benzimid azole compounds, 2 a-tert. butyl-1-methyl 5 a-propyIthio -6- [(4-me thy1ρipérazine-to-1 yl) - thiocarbonylamino]-benzimidazole derivatives, 2- tert. butyl-I-benzyl -5- propylthio -6- [(2- - methylpiperazine1- lo '-yl) - thiocarbonylamino]-benzimidazole derivatives, 2 a-tert. butyl-5-me thoxy -6- [(4 methyl-4 pyridinyl-piperazine 1 yl) thiocarbonylanino] - benzoimidazole, 2 a-tert. butyl-1-ethoxycarbonyl ~méthoxy 5 and 6 - [ (4 a-méthy1-to-4-oxido-piperazine -1- ylbenzoyl) - thiocarbonylamino]-benzimidazole derivatives, the T *>' 2 tert-. - butyl 1 a-diméthylearbamoyl - ^ - methoxy -6- [(4 methyl-4-oxido-piperazine -1- ylbenzoyl) - thiocarbonylamino]-benzimidazole derivatives, . 2 a-tert.-goal the Y 1 and 1 a-methanesulfonyl-5-methoxy-6 - [(4 methyl-4-oxido willwill pipéra.2innate -1--yl) lamino]-benzimidazol - thiocarbony, 2- tert. butyl -1- 2methyl -5- methoxy -6- [( ^ - méthy1- 4 pyridinyl-piperazine-îû1- ylbenzoyl) - thiocarbonylamino]-benzimidazole derivatives, . 2 a-tert.-to-buty 1 a-1 benzyl-5-methoxy-6 - [(4 a-méthyl~4-oxido-piperazine d-yl) -] thiocarbQnylamino-benzimidazole derivatives, 2 a-tert.-to-butyi-to-5-chloro 6 - [(4 methyl-4 pyridinyl-piperazine 1 yl) - : v-thiocarbonylamino] - benzimidazole derivatives, ' 5 2 a-tert. butyl-1-ethoxycarbonyl 5-chloro 6 - [(4-me the Thyl-a 4 a-oxydopipérazine -1- therein1) thiocarbonylamino] a-benzinidazole -, .•2 tert-. - butyl I diméthylcarbanoyl-to-5-chloro 6 - [(4 a-jfléthyl-to-4-oxido-piperazine -1- ylbenzoyl) - tMoearbonylamiiio] a-berzimidazolè, 2 a-tert. butyl-1 a-méthanesuifonyl and 5-chloro 6 - [(4 methyl-4 a-oxyào - 0 - piperazine1- ylbenzoyl) - MC iocarbonylamino] - benzoimidazole, 2 a-tert. butyl-1-me the Thyl-to-5-chloro 6 - [(4 methyl-4-oxido-piperazine -1- ylbenzoyl) - thiocarbonylamino]-benzimidazole derivatives, 2 - tert-. - butyl I-benzyl -5- chlor -6- [C4-to-mémé.thyl-to-4-oxido-piperazine -1- ylbenzoyl) -] thiooarbonylamino-benzimidazole derivatives, 5 * - 2 a-ktettbtttyl-a 5 a-prdpylfehio and 6 T-(1-methyl 4 pyridinyl-piperazine 1 yl) - ' thiocarbonylamino]-benzimidazole derivatives,: 2 - tert. butyl-1-ethoxycarbonyl 5 a-propylthio and 6 - [ (1-methyl 4-oxido-piperazine -1- ylbenzoyl) - thiocarbonylamino]-benzimidazole derivatives, ~5V~ 06816 2 a-tert. butyl-1 a-diEéthylearbamoyl-a 5 a-propylthio and 6 - [ (1-methyl 4 pyridinyl-pipéracine -1- ylbenzoyl) - thiccarbor.; ylmethyl] the benzimidazole -1 2 a-tert. butyl-1 a-E.éthanesulfQnyl-a 5 a-propyithic and 6 - [(1 a-méthyi-to-4~oxido-piperazine 1 yl) *] thioearbonylaEino-benzimidazol - 2 a-tert. butyl-1-me the Thyl-a 5 a-propylthio -6- [(1-me the Thyl-to-4-oxido-piperazine -1- therein1) - thiocarbonylamiuo] a-benziaidazole, 2 -1 the R T I - 1 - 1 - T-drunk Y-R-O-Py and Bas zy 1 - 5 - p 11 h-I-O--6- [(1 - oxido - 1 - 4 T-mth of HY - piperazine1- ylbenzoyl) -] thiocarbonylaœico-benzimidazole derivatives, 2 tert-. a butyl - -6- [(4 A-Eéthyl-to-4 pyridinyl-pipérazine~1 yl) - thiocarbonylamino]-benzimidazole derivatives, 2 a-tert. butyl-1 a-e mC - oxycarbony16- [(4- oéthyl-to-4-oxido-piperazine -1- ylbenzoyl) -] thiocarbonylanino-benzimidazole derivativesF. 2 - tert. butyl-1 a-dimé - thylcarbamoyl6- [(4 a-aéthyl-to-4-oxido-piperazine -1- therein1) - thiocarbony1the amino] Ben zimida zole derivatives, 2 a-tert. butyl-1-me thane was sulfony1 -6- [(4-me thy a 1- 4 pyridinyl-pipe - razine1- yj) -] thiocarbanylamino-benzimidazole derivatives, 2 - tert. butyl-1 a-mémé .thyl and 6 T- (4 a-oéthÿl-to-4 pyridinyl-piperazine 1 a-yj) - * thiocarbony1the amino]-benzimidazole derivatives, 2 a-tert. butyl-1-benzyl 6 - [(4 methyl-4 pyridinyl-piperazine 1 yl) thiocarbonylamirio]the benzimidazole>" THE N - [2- ter. - butyl 5-methoxy '-benzimidazol-to-6 yl] a-dithiocarbaaate of s - (2- carboxyethyl)* THE K - [2- ter. a butyl - -1- - l-oxycarbonyétb5> - ttéthoxy-benzimidazol -6--yl}' - s-dithiocarbamate (~2 carboxyethyl), THE H - [2- tert. butyl -1- - thylcarbamoyldimê5t-reme - hoxy-to-benzimid azole compounds -6- ylbenzoyl] a-dithiocarbaaate of&- (2- carboxyethyl)* THE N - [ 2- tert.-to-buty1-1- méthanesulfony1-to-5-methoxy-benzimidazol -6~-yl} - s-dithiocarbamate (2-carboxyethyl), the n - [2~tert. butyl -1- methyl -5- - methoxy-benzimidazole derivatives6--yl] - dithio-" carbamate 5 - (2-methoxyethyl), N [2 a-tert. butyl-1 benzyl-5-methoxy-benzimidazole derivatives thereof 6 yl] dithiocarbamate s - (2-carboxyethyl), H [2 tert-. - butyl 5 chloro-benziEida2ole-to-6 yl] a-dithiocarbaeate of s - (2-carboxyethyl), N [2 a-tert.-to-buty1-a 1 a-e thoxycarbony1 -5- - chloro-benzimidazole derivatives6--yl} - dithiocarbamate e - (2-carboxyethyl), H [2 a-tert. butyl-1 a-dimethylcarbamoyl-5 chloro-benzimidazol-a 6 - -yl] dithiocarbamate of s - (2-carboxyethyl), K-ter "[2". - butyl-L aéthanesulfonyl - ^ - chlorophenyl benziïsidazûXe-concerns a-yll **' dithiocarbamate e~(2-carboxyethyl), B. - [2 tert-. - butyl 'l Me the Thyl - ^ - chlorophenyl benziEidazole to e-ylj-to-dithiocarbaEate of s - (2-carboxyethyl), The n - [2 tert-. - butyl 1 - beiiiyl-to-5 Ch mantenute-benzimidazol-to-6 yl] - dithiocarbamate - O (2-carboxyethyl), K [2 a-tert. butyl-5 a-propylthic-benzimidazol-to-6 yl] dithiocarbamate s - (2-carboxyethyl), β-i' 2 a-tert. butyl-1 a-éthoxycarboriyi-a 5 a-propylthio-to-benzimid&zole derivatives thereof 6"-yl] dithiocarbamate of s - (2-carboxyethyl), H [2 a-tert. butyl-1 a-diinéthylcarbamoyl-a 5 a-propylthio-benzimidazol-to-6 yl) - carbamate s - (2-carboxyethyl)V. H [2 a-tert. butyl-1-methanesulfonyl - ^ - propylthio-benzimidazol-to-6 yl] dithiocarbamate s - (2-carboxyethyl), n [2 a-tert. butyl-1 a-méthy1-a 5 a-propylthio-to-benaimidazole-to-6 yl] carbamate s - (2-carboxyethyl), N [2 T-an ERT. buty - 1 - 1 - ylbenzyl - 5 propyl thio benzimid azole 6 yl]* dithiocarbamate e - (2-carboxyethyl)" n [2 a-tert, butyl-benzimidazol-to-6 yl] dithiocarbamate of s - (2-carboxyethyl), N [2 a-tert. butyl-1 MC-oxy - 1 - b ℮ arbony C. ℮ nzimidaz - ol 6 Y of i 1 j -d hiocarbamate of s - (2-carboxyethyl), Hr - [2 tert-butyl--1 · - - a Dime thylcarbamoyl-benzimidazol-to-6 yl] dithiocarbamate of s - (2-carboxyethyl), s [2 a-tert. butyl-1-methanesulfonyl-benzimidazol-a 6 a-yll dithiocarbamate s - (2-carboxyethyl), 5 - {2 tert-. - butyl 1 methyl-benzimidazol-th yl} - dithiocarbamate-of - (2-carboxyethyl), K -|2 Te rt.-butyl 1 a-beuzyl Ben ζ imadazo there and then 6 yl) - di-thioçarbaiaate of s - (2-carboxyethyl), the n - (2-isopropyl benzimidazol-to-5 yl] dithiocarbamate of s - (2-carboxyethyl), melts at 112 - 115 °c, ii-a [2-isopropyl 6 - (4 a-oéthyl-piperazine and 1 - ylbenzoyl) - thiocarbonylaminolbenzimidazoie, melts at 144 - 147*0. Example?■ in operating the s as follows The composition : (for 1c.cc0 comprinés) 2 a-tert. butyl~6- [(4 born thylpipéra zine derivatives-1- therein1} thiocarbonyîamino1 - benzothiasole500G c wheat starch 790 grams stearic acid 30 grams magnesium stearate 30 g to 400 g water Q.S. talcum. Extender is a mixture of the 2 tert-butyl 6 - * - [(4-methylpiperazine-1 yl) - thiocarbonylamino]-benzothiazole derivatives and 500 g of wheat starch with iJOO grams of deionized water and then about is moistened uniformly by a complement of 600 g of deionized water * is massaged the mixture until a slightly plastic mass is passed through a sieve with a mesh size of about 3 mm " is then dried and is again passed through a sieve * May be prepared analogously tablets containing another compound of the example 1 or a compound examples 2 to 5 th " as active substance. Example 8 By operating as in example 7, another alternative is to prepare tablets containing one of the compounds mentioned in the example 6. The invention also relates, as new industrial produced, the compounds obtained by the comfortable out the method defined above; these products are however not protected by this patent®©•* Leu at bends in therapy. The invention relates to a process for the manufacture of novel benzazole derivatives of the formula I <IMAGE> (I) in which R1 represents an optionally 4-substituted piperazino group or a group of the formula R2-alk-X2-, R2 represents optionally esterified carboxy or represents hydroxymethyl, alk represents lower alkylene or lower alkylidene, X1 and X2, independently of one another, each represents oxygen or sulphur, Ph represents 1,2-phenylene optionally substituted as well as by the group R1-C(=X1)-NH-, X3 represents oxygen, sulphur or optionally substituted imino, and R3 represents optionally fluorine-substituted lower alkyl or cycloalkyl, and their salts. The compounds of the formula I, which have proved to be excellent micro- and macrofilaricides and schistosomacides, are manufactured according to methods known per se. d. -. a new benzazole derivative of formula I wherein represents a piperazino group optionally substituted in position 4 or a group of formula - the rg-Alk named xG, RG is an optionally esterified carboxyl group or hydroxymethyl group, alk represents a lower alkylene or alkylidene, and named xG represents each, independently of one another, 1' oxygen or sulfur, pH value represents a group 1,2- phenylene optionally having substituents other than the group Ε ^ -0(≈ Χ ^) - - ΝΗ, xi represents 1' oxygen, sulfur or an imino group optionally substituted and Rj represents a lower alkyl group or cycloalkyl which is optionally substituted by fluorine, ,the n or a salt, especially a pharmaceutically acceptable salt for 1' pharmaceutical use. - 2 - A compound of formula according to paragraph d, wherein e ^ represents a group.1- piperazino optionally substituted in position 4 by lower alkyl, hydroxy lower alkyl wherein the hydroxy group is attached at position farther than the alpha position, and/or oxidation, or on the other hand a radical of the formula - the rg-Alk named xG wherein to Eg represents a carboxy group optionally esterified by a lower alcamol or hydroxymethyl, alk represents a lower alkylene group or lower alkylidene and named xG represents a thio-bridged or oxy, and X>tbioxo J represents a group or oxo, pH value represents a group d, 2-phenylene which is optionally, in addition to the group. Ε · ^ - 0 (·Χ ^) - ΝΗ -, of lower alkyl, lower alkoxy, lower alkanoyl, halogeno or/and trifluoromêthyle, the X ^ represents a bridge-oxy, thio or imino optionally substituted with lower alkyl groups, the di - (lower alkyl) - substituted amino - (lower alkyl), phenyl or phenyl lower itself optionally substituted by lower alkyl groups, lower alkoxy and/or halo, lower alkenyl, or lower-alkoxy carbonyalcanoy the lower the1 , lower alkane sulfcnyle, a mono - or di - (alkyl IFN greatly accelerated laugh) - c-ARB with&Weirdsville or alkylene - or 5an aza - -, 3and oxa - - or 3- thia alkylenecarbamoyl containing 5 to 8 ring members, and bj represents lower alkyl or cycloalkyl-ii to 6 membered optionally having fluoro substituents, or a salt thereof, especially a pharmaceutically acceptable salt for use ' pharmaceutical. 3 - A compound of formula ii according to paragraph 1" wherein R ^ represents a group 1- optionally substituted in position 4 pipérasino by lower alkyl, hydroxy lower alkyl wherein the hydroxy group is attached at position farther than the alpha position, and/or oxidation, or on the other hand a radical of the formula R ^ - ^ - alk-X wherein represents a thio-bridged or oxy, and represents a thioxo group or oxo, pH value represents a group 1,2- phenylene optionally having, in addition to the group Κ ^ -0(≈ Χ, ^) - NH-alkyl - lower, lower alkoxy, lower alkanoyl and/or halo, represents a bridge-oxy, thio or inino optionally substituted by lower alkyl groups, alkyl di (lower alkyl) - substituted amino - (lower alkyl), phenyl or phenyl lower itself optionally substituted by lower alkyl groups, lower alkoxy and/or halogen, lower alkenyl, lower alkanoyl or lower aleoxycarbonyle, and R ^ represents lower alkyl or cycloalkyl 3 to 8 membered optionally having fluoro substituents, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 4 - A compound according to paragraph 1 of formula S wherein R ^ represents a group 1- piperazino, i * i (4 * aifcyle infer: th ' URs) - pipéracino containing up to 4 c has blinds rbone Inc is read s in the lower allele group, 1- (4 - alkylphenyl® ittférieur~4-oxido} piperazino - containing up to 4 carbon atoms included in the lower alkyl group or 1- [4 - (hydrox 5 carbon atoms inclusive, the di - (lower alkyl) - carbamoylimino containing up to δ carbon atoms inclusive or phenyl-Calkyl inféri €) - containing imino until 10 carbon atoms inclusive and RG represents a lower alkyl group branched alpha or straight chain attached by a secondary carbon atom and containing up to 4 carbon atoms inclusive -, or a salt thereof, in particular a salt acceptable carrier " 5 - One compound according to paragraph 1 of the formula S in which R ^ represents a group 1piperazinc -, 1 - (4~alkyle lower) - piperazino containing up to 4 atoms of carbon included in the lower alkyl group, 1 - (4-lower alkyl - '^ - oxido) - piperazino containing up to 4 carbon atoms included in the lower alkyl group or 1 - [4 - {hydroxy ^ înférieur)] piperazino - wherein the hydroxy group is attached at position farther than the alpha position and the hydroxy lower alkyl group contains up to 4 carbon atoms inclusive, or on the other hand a group of the formula R ^ - alk-' a-Xgdans which represents a carboxy group or lower alcoxycarbônyle total up to 5 carbon atoms inclusive or hydroxymethyl, alk-' represents a lower alkylene group containing up to 4 carbon atoms inclusive and named xG represents oxygen or sulfur, and represents hydrogen " a lower alkyl group containing up to 4 carbon atoms inclusive, lower alkoxy containing up to 4 carbon atoms inclusive or halogen with an atomic number up to 55 included, the X ' j represents a bridge alkyloxy, alkylthio, imino or alkylimino lower containing up to 4 carbon atoms inclusive and represents a lower alkyl group branched alpha or to straight chain connected by a secondary carbon atom and containing up to 4 carbon atoms inclusive, or a selde this compound, in particular a salt acceptable for pharmaceutical use. 6 - A compound according to paragraph 5 of formula la represents a group 1 - (4-lower alkyl) - piperazino group containing up to 4 carbon atoms included in the lower alkyl group, 1 - (4-lower alkyl-4-oxido) - pipéranino containing up to 4 carbon atoms included in the lower alkyl group or 1- [4 - (hydroxy lower ^ - piperazino wherein the hydroxy group is attached at position farther than the alpha position and the hydroxy lower alkyl group contains up to 4 carbon atoms inclusive, or on the other hand a group of the formula H ^ - alk-' a-named xG - wherein represents a carboxy group or lower alkoxycarbonyl containing total up to 5 carbon atoms inclusive, alk-* represents a lower alkylene group containing up to 4 carbon atoms inclusive and named xG represents sulfur, and represents hydrogen, a lower alkyl group containing up to 4 carbon atoms inclusive, lower alkoxy containing up to 4 carbon atoms inclusive or halogen atomic number up1 to 35 included, represents a thio-bridged and e ^ aliryle represents lower ratified alpha or straight chain connected by a sputtering atose secondary carbon and containing up to 4 carbon included muted, or a selde this compound, in particular for the salt is acceptable for pharmaceutical use. ? - A compound according to paragraph 4 of formula la represents a group 1 - (4-lower alkyl} - pxpératino containing up to 4 carbon atoms included in the lower alkyl group and a group omega-carboxyl - (lower alkyl) - thio-containing up to 4 carbon atoms * included in the lower alkyl groups, and R ^ represents hydrogen, a lower alkyl or lower alkoxy group each containing up to 4 carbon atoms inclusive, x * j represents a thio-bridged and RG is a alpha-branched lower alkyl group containing up to 4 carbon atoms inclusive, or a salt thereof, especially a pharmaceutically acceptable salt for 1' pharmaceutical use. 8 - A compound according to paragraph 5" of formula la ^ represents a group 1 - (4-lower alkyl) - pipér&zino containing up to 4 carbon atoms included in the lower alkyl part or on the other hand a group omega-carboxyl - (lower alkyl) - thio-containing up to 4 carbon atoms included in the lower alkyl part, and R ^ represents a lower alkoxy group containing up to 4 carbon atoms inclusive, the X ' ^ represents a thio-bridged and RG lower alkyl branched alpha containing up to 4 carbon atoms inclusive, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 9 - The 2 a-tert. butyl -6- [(4-methylpiperazine-I-yl) thiocarbouylamino} - benzothiazole compound, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 10 - The 2 a-tert. butyl-5-methoxy-6 - [(4 a-néthylpipérazine -1- ylbenzoyl) - thiocarbonylamino]-benzothiazole derivatives, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 11 - The 2 tert-butyl 5 - *' * platinic 6 - [(4-methylpiperazine -1- ylbenzoyl) - thiocarbonylamino]-benzothiazole derivatives, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use * 12 - The 2 a-tert. butyl-5 a-Béthyl-a 6 - {(4-methylpiperazine " 1- yl derivatives; - thiocarbon; YlaEino] a-benzotbiazole, or US salt " in ES particular U.S. salt acceptable for pharmaceutical use. 1p - the 2 a-tert. butyl -6- [(4 a-aéthyl-to-4-oxido-piperazine~ 1--yl} - thioc&rbonylanino]-benzothiazole derivatives, or US salt, especially a pharmaceutically acceptable salt for pharmaceutical use. 14 - The 2 * - tert. butyl-5-methoxy " 6 - [(4 methyl-4 pyridinyl-piperazin-l-yl) -] thiocarbonylacylamino-benzothiazole derivatives, or a salt, especially a pharmaceutically acceptable salt for pharmaceutical use. 15 - The 2 a-tert. butyl-5 a-chlôro and 6 - [(4 methyl-4~oxydo-piperazine -1- ylbenzoyl) -] thiôcarbonylamino-benzothiazole derivatives, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 16 - The 2 a-tert. butyl-5 a-méfchyl and 6 - [(4 a-aéthyl-to-4-oxido-piperazine -1- ylbenzoyl) - thiocarbônylâmino] a-bertzothiazole, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 1? - The 2 a-tert,-butyl 5 a-ûéthoxy-a 6 GBP - {4 - (2 hydroxyethyl) - piperazine -1- ylbenzoyl] ~thiocarbonylaainoj-benzothiazole derivatives, or a salt thereof, especially a pharmaceutically acceptable salt for 1' use pharmaceutiqu th. 18 - The 2 a-tert.-to-bütyl-to-6 ^ - [4 - (2 hydroxyethyl) - willwill pipéra * - zine derivatives1- ylbenzoyl] a-thiocarbonylaainojj-benzothiazole derivatives, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 19 - The 2 a-isoDropyl-to-6 ^ - [4 - (2 hydroxyethyl) - piperazine -1--yl} - thiocarbonylaminoj-benzothiazole derivatives, or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use * 2C - n-[2 a-tert. butyl -5- wa3cy of-benzthiazole -6- ÿl]" - s-dithiocarbamate (2 a-carboxyêthyle), or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use * 21 - The H - [2- tert. butyl-Bas20thiazol -6- ylbenzoyl] dithiocarbamate of s - (2- carboxysthyle), or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 22 - N-[2 a-tert. butyl-5' chloro-benzthiazole-a 6 a-ylJdithiocarbamate of&- (2- carboxyethyl), or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 23 - ' N -the L2- tert. butyl -3the Thyl Ben - born2, - othiacole6- - l-dithiocarbamate (2- carboxyethyl), or a salt thereof in particular a salt acceptable for pharmaceutical use. 24 - N-[2 a-tert. butyl - ^ - methoxy-bensothiazole-concerns yl] dithiocarbaraate s - (2 a-carboxypropyl), or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 25 - N-[2 a-tert.-to-butyl~5-to-méthûxy-benzthiazole-a 6" yl3 dithiocarbamate s-carboxynéthyle ., or a salt thereof, especially a pharmaceutically acceptable salt for pharmaceutical use. 26 - The k-[tert. butyl-5-methoxy-benzothiaaole and 6 a-yl3 " thiocarbanate OD - (2- carboxyethyl). 2? - A compound according to any one of paragraphs 1 to 26 having an action anthelainthique. 28 - A pharmaceutical preparation containing a compound according to one of the paragraphs 1 to 26 and supports and usual pharmaceutical vehicles. 29 - Process for the preparation of a new derivative of formula benzacole (D. wherein represents a piperazino group optionally substituted in position 4 or a group of the formula R2" alk-X2"" $2 represents carboxyl group optionally endorsed or hydroxymethyl, alk represents a lower alkylene or alkylidene, and or their salts, characterized in that: a) is condensed together to compounds of the formula formulas II and III THE R - in which represents hydrogen and Y2 and Y ^ together form a group of the formula "=c=x ^ or one of Y, Y and Y2 represents a group of formula - (X-* ^) of c - ^ ^ therein wherein Y represents an eliminable, and the other, as well as y ^, represents hydrogen or, when R represents a group R ^2- alk-X2"" represents a cyano group and Y2 and yj represent hydrogen, or salts thereof, or b) in a compound of formula IV V CIï), wherein Y is a radical ^ convertible into a group of the formula R ^ ^ ^ - X-DC) -, or a salt of such a compound, is converted therein into a group ^ ^ c is of the formula R - (=x * j) -, or c) NC cyolise a compound of formula V R1- C-NH-pH. VT the TT (V.) wherein one of Y11 ^ and Y represents a group of formula - ^ ^ ^ - DC therein Rj and the other a removable remains, and is oxo functionality optionally modified, or a salt of such a compound, and if desired, converting a compound of the invention thus obtained into a further compound of formula I and/or a salt according to the invention thus obtained into the free compound or another salt. 30 - A method according to paragraph 29, characterized in that by *' involves having a compound obtained as an intermediate in a process step is carried out and any stages a missing or special form a starting material in the reaction conditions or used state dérivééventuellement state of salt. 31 - Irocédé according to a paragraphs 2¼ and 30 ., characterized in that condensed therebetween réponétant compounds. formulae II and III above wherein Y represents ^ 1' hydrogen and Y2 together form a group of the formula=0Χ=^ or their salts or, in a compound of formula IV wherein Y ^ represents a group of formula THE C - (" THE Xthe n ) - X.2- alk-Ch=0 or - C. (the X *1) - X.2- alk-Ch20K, oxidized therein, - in a group of the formula - (=the X ^) of c - the X2- alk-COOH. 32 * Preparation method. pharmaceutical preparations, characterized in that mixing a compound according to one of the paragraphs 1 to 2? with conventional pharmaceutical carriers and vehicles. 33 - The method examples 1 to 6 and the resulting products. 34 - The novel compounds mentioned in the examples 1 to 6. 35~The starting products and/or novel intermediates used in the method of paragraph 28 to 31 and 33. 36 - A compound according to any one paragraphs 1 to 2? for use in a method of therapeutic treatment of the body in human or veterinary medicine. 37 * Use of the compounds according a paragraphs 1 to 27 for the preparation of pharmaceutical preparations for the treatment of parasitic helminths. 38 - Compounds according to one of the paragraphs 1 to 27 as anthelmintic agent.