MXPA96005256A - Aminofenilsulfonilureas aciladas, procedures for its preparation and its use as herbicides and plan growth regulators - Google Patents

Abstract

The present invention relates to a compound of formula (I) or a salt thereof, wherein W1 is an oxygen or sulfur atom, W2 is an oxygen or sulfur atom, n is 0, 1, 2, 3, R is halogen, alkyl or alkoxy, independently of other substituents R if n is greater than 1, R1 is hydrogen or a substituted or unsubstituted hydrocarbon or hydrocarbon radical, R2 is hydrogen or a substituted or unsubstituted hydrocarbon radical, or the group NR1R2 is a heterocyclic ring it has from 3 to 8 of canillo, which is substituted or unsubstituted and contains the N atom of the group NR1R2 as a hetero-ring atom and may contain additional hetero-ring atoms, R3 is an acyl radical, R4 is hydrogen or an aliphatic hydrocarbon radical; X, Y are, independently of one another, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, wherein each of the 3 radicals mentioned in the last is unsubstituted or is substituted with one or more radicals of the group that consists of halogen, C1-C4 alkoxy and C1-C4 alkylthio, or C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 alkenyloxy or C3-C6 alkynyloxy, and Z is CH or

Description

STACKED AMINOFENILSULFQNILUREAS. PROCEDURES FOR ITS PREPARATION AND ITS USE AS HERBICIDES AND REGULATORS OF PLANT GROWTH The invention relates to the technical field of herbicides and plant growth regulators, in particular herbicides for selective control of broadleaf grasses and grasses in harvesting useful plants. It is known that phenylsulfylureas which are substituted by heroic cyclic substitutes and having an amino or amino group functionalized on the phenyl ring have herbicidal and plant growth regulating properties (EP-A-1515; EP-A-7667). (= US-A -? +, 3 &3, 113) 5 EP-A-30136 (= US-A-t +, 39L, 50?), US-A-4, ß92,946j US-A-4, 9ftl, 509; EP-A-11651 & US-A-4,664,695, US-A-4,632,695)). Phenylsulfonylureas containing, in the phenyl ring, a carboxyl group or a function derived from the carboxyl group in the 2-position and a group of N-alkyl-N-acyl-amino in the 5-position have also already been proposed in the German Patent Application P 42 36 902.9 < WO 94/10154). Surprisingly, it has now been discovered that certain phenylsulfonylureas which are substituted by heterocyclic substitutes are particularly suitable as herbicides and plant growth regulators. The present invention relates to compounds of the formula (I) and salts thereof. where 1 is? Nt «Oxygen or« .uliuro,) 2 is an oxygen or cultured atom, n is 0, L, 2, 3, preferably C) or 1, in particular f), ll. R is halogen, alkyl or alkoxy, ndependien + emerrt e of ot roo sub ii tutos R if n is greater than 1. P1 is hydrogen or flee ocar bonus substituted or not s? Bs + i + ui do or radical of hydrocarbon, R2 is hydrogen or hydrocarbon radical or substituted or not? The NR1R2 group is a heterogeneous group that has 1 to 0 or more rings, which is subsumed or non-existent and contains the + N group of the NR group. * R2 as an atoin of he * ero-b ring and may also contain additional ring-ring atoms, R3 is an acyl radical, R * is hydrogen or a hydrocarbon radical ali < \ + i co, X, Y i dependently on another are halothane, alkyl! of Oi-Cß, Ci-C alkoxy, C-Ce alkylthio, wherein each of the last 3 radicals mentioned is substituted or. or substituted by one or more radicals of the group consisting of halide, C1-C4 alkoxy and Ci-C, alkyl, or C3-C6 cycloalkyl, C2-C alkenyl, C2-Ge alkynyl, alkemloxy ID of (.3 -Ce or C2-0 alkyloxy), V is CH or N. In the formula (1) and in the formulas used below, the alkyl, alkoxy, haloalkyl, haloalkoxy, alkyl and alkyl radicals alkyl + 0 and the radicals The corresponding unsaturated and / or substitutes can be in each case on a 1-chain or branched chain on the carbon skeleton. _.? it is not specified, the minor carbon skeletons, for example that in Jo 1 to 4 volumes it is ca - oono, or, in the case of unsaturated groups, that have from 0 to 0 - carbon atom, they are Preferred for these radicals are alkyl radicals, including those in the mixed body meanings, such as alkoxy, haloalkyl and the like, are, for example, methyl, e-tyl, n- or? -? p radicals. It, n--, 1-, t- or 2-butyl, pentiium radicals, radicals of b hex 1I0, such as n-heyl, 1- ex do and 1, ü-dirnetylbutyl, and radicals of hep-tjio, such as heptium, 1-rnet 11 hexyl, and 1,4-dimethyl dpen, the radicals of which can not be reduced to the meaning of the possible unsaturated laides they correspond to alkyl radicals, and alkenyl is, for example, aillo, l-rnet? lprop-2-en-l-1, 2-rnet? lpro? -? - en-l-byl, but-2 -in-l -yl, but -3 ~ in-l, l-me dbut-3-en-l-do and l- eti lbut -2-en-l-1 lo; and alkyl is, for example propound gdo, bu-2 -m-l-? lo, bul -3- m- 1 - i lo or l -rnet t Ib? t -3- j n- 11 o. Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, alkenyl and alkyne are alkyl, dear, or alkenyl which are partially or completely substi tuted by I prefer to use fluorine, chlorine and / or bromine, in particular fluorine or chlorine, for example OF3, CHF2, CH2F, or3C. "2, CH2FCHCI, CCI3, CHCI2, and CH2CH2CI, haloalkoxy is, for example, OCF3, OCHF2, OCH | F, CF3CF2O, 0C122Cr and OCH2CH2CI; the corresponding statements apply to haloalkyl and other subsitic radicals halogen.A hydrocarbon radical is one in straight, branched chain. or cyclic and radical of saturated or unsaturated iliphatic hydrocarbon or aromatic, for example alkyl, or alyl, alkyl, cycloalkyl, cycloalkylene or ardo, preferably alkyl, alkylene or alindole having up to 12 carbon or cycloalkyl which has ring or phenyl atoms, the corresponding statements apply to the hydrocarbon radical .. b Ardo is a mono-, bi- or polycyclic aromatic system, eg, background, naphthyl, t et rah drona f -t 1 lo, indenyl, indando, pen-t alendo, fluorofend and the like,? "> fep blemen-te phenyl; aryloxy is preferably an oxy radical corresponding to the aforementioned aryl radical, in particular phenoxy. Heteroaryl or a heterocyclic radical is a mono-, bi or polycyclic aromatic system in which at least one ring contains one or more heteroate, for example pin di Lo, pri runidini Lo, pridazindo, pirazindo, tende, thiazolyl, oxazolyl, fuplo, pyrrolyl, pyrazolyl and nidazolyl, and also bicyclic or aromatic compounds For example, quinolinyl, benzoxazole and the like, Hete roa rilo tanbLen includes an omatic heteroaryl ring, preferably having 5 or 6 members and containing 1, 2 or 3 of ring-ring, in particular of the gi upo consisting of N, o and < ? In the substitute case, the Roman ring may also be benzo fused. A radical hetei or the ring or ring may be saturated, unsaturated or het eric aromatic; it contains one or more atoms of het-ring, preferably of the group which is on the N, or y; prefermente it has 5 or 6 members and contains 1, 2 or 3 atoms of het gold -and 1 o, radical R I can be, for example, a ring het eroaro at i co as defi e before or is a? Partially hydrogenated ad? Cal, such as oxy ramie, pyrrole ddo, piperiddo, ?? Perazi n lo lo, dioxol iu 1 o, morfol indo or t eti there drof ui i 1 - possible subsitutes for a substituted heterocyclic radical are the substitutes mentioned below, and also oxo. The oxo group can i 'rpr in the ring-ring atoms that may exist at different oxidation levels, for example in the case of N and b Substituted radiols, such as substituted hydrocarbon radicals, for example alkyl, substituted, alkenyl, alkylaryl, aryl, phenyl and benzyl, or substituted heteroaryl, a substituted cyclic radical or ring or a radical or cyclic subst i -t ui do, if appropriate with proportions aromatics are, for example, a substituted radical which is The unsubstituted parent substance, wherein the substitutes are, for example, one or preferably 1, 2 or 3, radicals of the group consisting of halide, alkoxy, haloalkoxy, aiq? D + io. , hydroxy, arnino, nit or, cyano, acid, Lí? alkoxycarbonyl, alkyl carborum, forni or, carbarnoyl, mono- and di-alkoxycarbonyl, substituted arnino, such as Lamino, mono- and dial quamy and alkylsulphyl, haloalkyl Isui-onyl, alkyl The fonilo, has Loal qui Isul oni lo and, in the case of radicals ci-cos, also alkyl, and haloalkyl, and the unsaturated O-ali radicals that correspond to the radicals containing saturated hydrocarbon mentioned, such as Alkenyl, Alkyl, Liqueni, Alkyl, Alkyl, and the like, in the case of radishes with carbon atoms, those having 1 to 4 carbon atoms, in particular L or 2 carbon atoms, are preferred. Substitutes of the group consisting of halogen, for example fluorine or chlorine, alkyl of O i - C ', preferably methyl or ethyl, Ci-Ci haloalkyl,. When the polymer is introduced, Ci-C¿ alkoxy, preferably inetoxy or ethoxy, C1-C4 haloalkoxy, nitro and cyano are a preferred rule. Methyl substitutes, b rnet 0x1 and chlorine are particularly preferred herein. The monoamine mono-or disubsti tute is, for example, to which the mo, dial q no ilar, acilarnino, aplamino or N-ard-N-lqui 1 -arninü. The optional substituted organ is O preferably being substi tuted or unsubstituted once or many times, preferably up to 3 times by identical or different radicals from the group consisting of halogen, C 1 -C 4 alkyl, C 1 alkoxy. C, 4, haloalkyl of Ci-C4, haloalkoxy coxy of C1-O4 and nitro, for example 0-, m- and p-to lo, b dirnet 11 f in 1 2-, 3- and -c Lorof enyl, 2 -, 3- and *. -tpf 1 uoro- y - t ri cLoi o f-eni lo, 2,4-, 3,5-, 2, b- and 2, 3 -d 1 chloro reni 1 oy 0-, in- yp -inet o 1 i llo. An acrylic radical is the radical of an organic acid, for example the adical one of an arboxylic acid, and 0 acid radicals derived therefrom, such. option or almont of N-substitutes, or the radical of carbonic acid monosters, optionally l-arbainic acid, optionally M-subst 1 t, thic acid, sulphonic acids, phosphonic acids, or phosphinic acids. Fícilo is, for example, beefy, alqui K, arf)? n? It, such (alkyl of d -C «) carbon, I-eni lcarboni Lo, where the ferulo ani o can be ^ instituted, for example as indicated above by phenyl, alkyloxycarbonyl, feuloxycarboxy, hencyloxycarbon or, cytoluene sulphide, alkylsulfin, n-alkyl-1-alanyl-al What are the radicals of organic acids? The invention also refers to all the stereoisomers included by means of the formula (T) and mixtures of the same. Said compounds of the formula (I) contain one or more asymmetric C atoms or also double bonds, which are not shown separately in the formula (I). The possible storeoisoiners defined by means of their sword form! specific, such as enantiomers, diasterers, and Z and E isomers, all are included by means of formula (E) and can be obtained from mixtures of stereoisomers b by normal methods, or otherwise. In this way, they can be used in combination with the reaction medium, or stereochemically pure starting substances. The compounds of the formula (T) may be salts or salts where the hydrogen of the group C_02-NH or also or at least 0 of hydrogen has been (for example of COOH and the like) is replaced by a cat in suitable for the farming. These salts are, for example, metal salts, preferably alkali metal or alkaline earth metal salts, in particular sodium salts and potassium salts, or also ammonium salts or b salts with organic amines. The formation of salts can also be carried out by adding an acid to the basic groups, such as, for example, ainine and alkylamide, suitable for . '*? They are strong inorganic and organic acids, for example HO 1, HBr, l-fc S0 «or I-INÜ3. The compounds of the formula (I) according to the invention, or salts thereof which are of particular We can find out where Rl is I-I or alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkynoxy, cycloalkyl, cycloalbum or bottom, wherein each of the < 3 radicals The aforementioned is substituted or not substituted and contains a total of up to 24 carbon atoms, preferably a total of up to 12, in particular a total of up to 0 carbon atoms, R2 Is I-1 or alkyl, at do, or rent it, where each Ib one of the radicals mentioned in the last one is subsumed or not substituted and with a total of up to /. Carbon atoms are preferable to a total of up to 12 carbon atoms, in particular a total of up to carbon atoms, or in group 0 It is a substituted or unsubstituted heterocyclic ring of 4 to 0 rings, where the group has a total of up to 4 carbon atoms,, < Totally total of up to 12 carbon atoms, b k3 It is because it has up to 24 carbon atoms, preferably up to 12 carbon atoms, < > It has a particle up to 8 carbon atoms, and it is H or alkyl, alkenyl, alkenyl, where each of the radical res mentioned *, the latter contains up to 12 atoms (He carbon, preferably 5 to 5 carbon atoms). The compounds of the formula (I) according to the invention, or salts of the compounds which are of particular interest, are those in which R 1 is H, C 1 -C 12 alkyl, O 2 -C 12 alkylene, 0 alkyl of O 2 -C 12, alkoxy of (.sub.1 -C.sub.12, alkenoxy of O.sub.2 O.sub.12, alkyloxy of C.sub.12 C, cycloalkyl of O.sub.3 -Ce or <:? cloalquen? 1 or of (.5-Ce), wherein each of the The radicals mentioned above are substi tuted or not substituted, for example, they are substi tuted by one or more radical radicals of the group consisting of halogen, cyano, acid, C0-R5, OR *, NR7R8, SR9, 50-R10 and 02 -RH, or substituted or unsubstituted forillo, I? 2 It is H, alkyl of O-C12, to the wanted of C2-C12 or alkenyl of C2-C12, where each of the res or radicals mentioned the latter is substi tuted or not substi tuted, for example, and substituted by one or more radicals from the group consisting of halogen, cyano, asido, C0R1 0R13 NR14 15 SR16, S0-R17 and 02-18, or the group b N 1R2 It is an erocyclic ring of 4 to 0 ring atoms, which may contain * up to 2 additional het ero-ani L atoms in the ring group consists of N, 0 and '-. and is not subsitute or is substituted by one or more radicals of the group consisting of allogen, Ci-Ce alkyl, NO2, N3 and CN, R3 E and C0-R19. C-R20 O2-R21, c0-R21 or C (-NR21) -R19. R * is H, Ci C3 alkyl, C2-C5 alkenyl or C2-05 alkindo, R5 is H, O1-C5 alkyl, C2-C5 alkenyl, 2-C5 alkyloxy, C1-O5 alkoxy , al) C2-C5-enoxi, C2-Cs-alkoxy, MR22R23 or OH-IA * E s II, at Ci-C5, at 1 or at 1 or Ci-O5, C2-alkano C5, dear alkaline of C2-C5, aLquindo of O-O5 or alloy Lqui n 1 Lo of O2 5, R7 Is H, Ci os alkyl, to the quemlo of C2-C5, alindo Ib do C2-C5, C1-C5-lcoxy, OO-OH3, or COOCH3, R8 is H, ai < Odo-Odo, at the end of (.2 - C5 or the group R R8 It is a heterocyclic anteroid of 4 to 8 ring atoms, 20 which may contain up to 2 atoms of hetero- in the ring of the group consisting of N, 0 and s and substituted or not subsumed by * one or more radicals of the group consisting of allogen, Ci -OH alkyl, NO2, N3 and ON, 'b R9 is H, Ci-O5 alkyl, the preferred C2-C5, O2-C5 alkynyl, to the Ci-O5 alkyl, at the C2-C5 lo al, L 2 It is Ci-Cs alkyl, C2-C5 alkenyl, O2-C5 alkyndi, Ci-Ci alkyloxy, C2-Cs alkoalkyl or a1 or 1 q or 1 n 11 or C2-Os. b Rd Is it the rent of C? -Cs, alcicle of C2-C5, alkyl of O2-O5, alkalyl of C? -C5, the 02-Cs alkeque, aloquindo of C2-C5, coxi to the quilo of C? -Cs, ci c. The 1-cyl of C3-Cs occloal beloved of C5 -Ce, i ts an analogue analogue to R5, l 'I'. '"13 It is a r * ad? Cal analogous to R6, It is a radical analogous to R7, Ris It is a drug analogous to R8, or the group is a group analogous to NR7R8, LL. R * is a r-dical analogous to R9, it is a radical analogous to io, id rs a 1 1 di cal analogue to Rl 1, R19 p, C12 alkyl, <O2 O12, 11x1, O1-O12 alkyl, Ci C12 alkyl, Oxyquinone, O1 O1, INOXI of (2-C12, qui cicloal the O3 -OS, cieloal queru the < le -OS C5, alky lamino Ci O12 quil dial \ rn not Ci - C &?..?, Alkoxy - N-Ci -C «-al qudaini not -N- O1-C4, where each of the 13 radi cals mentioned in the last one are substituted or not '.'l substituted for example is subs itu radicals or by one or RNAs from the group consisting of allogenic, cyano, gripping, 00-R24, 0R2S, NR26 R27 R2S, S0R29 S02 and 30, or a substituted or unsubstituted background , phenoxy or radical fem lamino, 0 E a radical analogous to Rl9, r > R2i is a radical analogous to Ri, 2 H, Ci -Cs alkyl, alkenyl-C5 O2, O2 alk ulo-C5, C1-C5, C2-C5 alkenoxy of aiquinoxi or C2-C5, where each of the above mentioned codes? The last one is substi tuted or not LO substituted, for example is substituted by one or radicals as the group consisting of allogenic, cyano, gripping, horiuno, ainino, mono- and di-substituted, C1-C3 alkyl, C1-C3alkylsulfinyl, Ci -C3 , alkyl sulphon of Ci -O3 and alkylthio of C1-C3, Lh R23 Is H, alkyl of Ci-C5, alkenyl of O2-O5, to the one of O2-Cs, I read Xi do C ~ Cs or to Lea not xi of C2 - C5, wherein each of the 5 radicals mentioned to ULT Irno is replaced oo subs ituido, for * example is substituted by one or more radicals from the group 0 consisting of allogeneic, Cuino, gripping, arnino, mono and disubstituted, O1-O3 alkoxy, C1-C3 alkoxy, to one of the C1-C3 foni and alq? i Is? lf 1 n that of C1-C3, or the group NR22R23 It is a heterocyclic ring 1 to NR7R8, preferably a ring and to 5 or more ring atoms, which may contain up to 2 additional hetero anil rings in the ring of the group consisting of N, 0 and y is substituted or unsubstituted by one or more radicals of the group consisting of halogen and (-?) Alkyl, 24 Es H, Ci-C3 alkyl, Ci-C3 alkoxy, NH2 or mono- or disubstituted aromo , 25 It is H, ai qui that of C1 - C5, alcam Lo of C2 - C5, alkynyl < Je C2-O5, C1-C5alkalkyl, C2-Csalkalkenyl, or al? .1 quinilo of C2 -Os, 26 £ H, C1-C3 alkyl, C13-C3-alkoxy, CO-CI-I3 or C0-H, R27 E II, C1-C3 alkyl, or the group NR26-R27 Wg up analogue to NR22R23 R28 is H, alkyl of O1-C3, aLoal < Only one of C-j. -O3, C2-C5 dear of, aloa 1 queru the O -OS at quinde O2 Os or Loa L chyle C - O5, R29 is alkyl -OS heard, aloalq do Oi -O5, alqueulo? of C2 -Os, to the qual of O2-O5, to Iquido of O2 O5 or to the qui rulo of O2 - ("5, R30 Is analogous to R, Wi Is 0 or *! -., preferably 0, i Is 0 or, preferably 0, X, Y independently of other '- * on.

I heard C, Ci-C alkoxy or Ci-C ^ alkyldio, wherein each radical of the 3 radicals mentioned above is substituted or unsubstituted by one or more radicals of the group consisting of halogen, Ci-alkoxy C4 and Ci-4 alkyl, or amino mono- or Ci-cycloalkyl, cycloalkyl * of C3-Ce, C3-Cs alkenyl or C3-O5 alkyletuloxy, and Is CH or N. Preferred compounds of the formula (1) according to the invention, the salts thereof are those in which l is H, Oi-Oß alkyl, to the wanted of O 2 -Ce, aJquj.ni Lo of C 2 -Ce, C 1 -C alkoxy, C 2 -C 4 alkoxy, O 2 -Okyloxy or cycloalkyl of Cs -Ce, wherein each of the 7 radicals mentioned above is subsumed or substituted, by one or more radicals of the group which consists of halogen, cyano, asido, C0-R5 0R6, NR P8, R9, O-RIO and O2-K1 *, or (e) that is subsumed or not substi tuted by radicals of the group consisting of halogen, C1-C4 alkyl, C1-C4 alkoxy, at the C1-O alkyl, C1-C4 alloalkoxy and nitro, RI is II, Ci -CA alkyl and nitro, 2 is H, alkyl from O-Ce, at the O2-Ce alkyl or at of C2-O6, wherein each of the 3 radicals mentioned lastly subsumed or not substituted by one or more radicals of the group consisting of -tlogeno, cyano, -isi or, C0R12, 0RI3, NR14R15 R16, 0-R1 and O2- 18, T ?? group NR1R2 It is a heterocyclic ring of 5 or 6 ring atoms, where it may contain * up to 2 additional ring hetero ring atoms in the ring of the group which consists of N and ü and is substituted or not substituted by one or more radiological groups of the group consisting of Ci -CA alkyi, R3 ES C0-R19, CS-R20, O2-R21 or C UNR21. 1 R "EH or OH3,. <? - Is H, OI-O3 alkyl, Ci -O3 alkoxy, NR22R23 or O H, R6 is H, alkyl OI-OA or haloalkyl < CI-CA, R7 Is H, alkyl of d-03, C1-C3 alkoxy, OO-OH3, 00 -H Ib or COOOI-I3, R8 It is ll to the uyl of Ci-03. or the group N 7 8 f an orbital ring of 15 to 6 ring atoms, which may contain up to 2 het atoms ero-ani Lio. Additional 0 on the ring of the group consisting of N and 0 and is substituted or unsubstituted by one or more alkyl radicals of Ci-C, R9 is H, C1-C3 alkyl or C1-O3 alkoalk, Ri ° It is Ci-C3 alkyl or Ci-O3 aloal quilo,! Rii is Ci-C3 alkyl. Ci-C3 -alkyl, O-C3-aleoxL, Ci-O2-alkyl, Ri2 Is a radical analogous to RS, 3 l-s a radical an logo, -? ß, i Is a radical analogous to R7, is FS a radical analogous to R8, or the group NRIARIS Is a group analogous to NR7 R8, R16 It is a radical analogous to R9, R17 It is a radical analogous to Ri °, Rlß EE sunradjca 1 ana Lo or 1, R 9 Is II, alkyl of Oi-Ce, to the quer of C2-Ce, alkyn? of O2-O6, Oj-Oe alkoxy, Ci-C-alkylthio, C2-C6 alkanoxy, O2-C-ylkyloxy, cycloalkyl of O3-Cs, Ci-C alkylamino, dialkylamino of Ci-CA or alkoxy of N-Ci CA -alkyl ainino of N-CI -OA, wherein each of the radicals mentioned at the last one is substituted or not substituted by one or more radicals of the group consisting of the genus, cyano, 00-R24, ÜR2S. MR26R27. c, R28. SOR29 and SO2R30. or a renoxy, renoxy or radicals of 1 in 1, which you replaced or not substi tuted by radicals of the group that with allogenous, alkylate Oj O, alooxi do OI -OA, to Loal quilo de Oí CA, loalco i of OJ -OA and nit r * o, R20 It is a radical analogous to 9, R21 Is a radLcal an logo to RH, R22 Is H, C alkyl? -CA O alkoxy do 0I-0A, wherein 10 each of the 2 radicals mentioned in the latter is subsituted or not substituted by one or more radicals of the group consisting of halogen, cyano, amino, amino mono- and di-alkyl of Ci -OA, alkoxy of d-O3, The base of C1-O3 and alkyl of Oi-C3, R3 is H, C1-C5 alkyl, the preferred of O2-O5, C2-O5 alkyloxy, O1-O5 alkoxy or C2-O5 alkenoxy . where each of the 5 radicals mentioned at the last subsumed or not subsumed, for example It is substituted by one or more radicals of the group consisting of halogen, nano, asido, ainino, amino mono- and d 1 subst d ui o, Ci -O3 alkyl, Ci-3 lcoxy, Ci-C3 alkylthio, alkylsul fonilo of Ci-C3 and 1 qu 1 u 1 í- 1 n 11 o of Ci-O3, I or the group NR 3 s a group analogous to NR7 R8, R2A Is H, Ci-O3 alkyl, C1 alkoxy -C3, MH2? > mono- or di-alkoxy mood of Ci -CA, R2s is H, Ci-C5 alkyl or halo of Oi-Os 20 is H or C1-O3 alkyl K'27 is II or C1-O3 alkyl or qru~o NR26 2 e a group analogous to NR22 23 R2S is H or Ci-O3 alkyl, 2 b R29 is Ci-C5 alkyl or Ci-5 haloalkyl, R30 e < analogous to R29, Wi is O or c._, preferably 0, is 0 or T., p re ferib 1 eme n te 0, one of the Y and X branches is halogen, Ci-C2 alkyl, Ci alkoxy -C2, b alkyl C1-C0, wherein each of the three radicals mentioned in the latter is substituted or not substituted by one or more radicals of the group consisting of halogen, Ci-C2 alkoxy and CiX2 alkylthio. mono or dll what 1 not yet do Ci --O2 / O? > r * ef eribLernent is halogen, methyl or ethoxy, and the other of the radicals is Y and X is C1-O2 alkyl, C1-O2 haloalkyl, Ci-C2koxy, Loa Ico xi Ci-O2 or alkyl C1-C2, preferably methyl or methoxy, and, Z is Cl-I or N, fi p re fe r 1 b 1 eme rit e OH. Particularly, what <; Preferred compounds of the formula (I) in accordance with the invention are salts thereof where R is H, alkyl of (-O, C, -O 2 -koxy, or phenine which is substi tui < not substi tuted by one or more radicals (the group consisting of hydrogen, the alkyl of O1-O2, the hydroxy of O1 -O2, the Loal of 0-j. -O2 and haloal cox 1 of Ci -O, R2 is H, alkyl of O1-O2 or C1-C2 alkyl, or the group NR1R2 is a heterocyclic ring of 5 or R ring atoms, which may contain up to one additional hot-ring atom in the ring The group consisting of N and 0 and is substituted or unsubstituted by one or more Ci -O2 alkyl or radicals, R3 is 00-R1, C R20 f) (? 2, R21 / R * is H or OH3, Ri 9 is II, O-CA alkyl, O 2 -OA alky, 02-O alkyloxy, 0 ° OA alkoxy, CI-OA alkyl thio, C 2 -OA alkoxy, to 02-OA quinoxy, cycloalkyl from O3-C6, to the one from Ci -CA, diaiquilami not from C? - OA, Leoxi from N -Ci-C2 to L < | u? lamírio of N-C1-C2, where each of the d? e? mentioned radicals < - The latter is substituted or not substituted by * one or more radicals from the group consisting of halogen and alkoxy or a phenyl or ioxy, which is substituted or not substituted by radicals of the group consisting of halogen, C1-alkyl - C2, Oxy O2 alkoxy, Ci-C2 haloalkyl and Ci-C2 haloaicoxy, R20 s an RI9 anion radical, and R2i is alkyl (C1-C3), C3 or C1-C3 alkoxy-C1-C2-lyl The preferred compounds of the formula (T) of con or urine with the invention are those wherein the group of the formula N1-I3 on The radical position in the position for the group CUi MR P2 and the eta position of the group SO2 ..

Preferred compounds of formula (I) of. The present invention also relates to processes for the preparation of the compounds of the formula (I) in which the combination of the above-mentioned radicals is preferred. conformity with the mvencioii or salts of the isms, which comprises a) reacting a compound of La fopnula (TI) I with a ca rbamat or het eroe ic Lico from 1 to fopn? La (i) in Jo n of R * it is faith neither it or alkyl of OI -CA subsu i or not subst it i i, or b) reacting an isocyanate The sulphorum of the! formul (LV) with a hoterocyclic amine of the formula (V) or c) do * eacc? o ?? ar a doro (Je sulfomlo de la formula with a heterocyclic amine (ie, the above formula (V) in the presence of an example, for example a cyan or metal at calme, such as cyanate sodium or potassium oi, or rl ) reacting a s? IFronnida of 1? previous formula f ri) with? n (t IO) i ocianate of the formula (VI I) in The presence of a suitable base, such as, for example, potassium carbonate or t riet ilarní na. where, the previous formulas (II) to (VLE), the radicals I ?, Rl, R2, R3. 4, ii, I, X, Y and 7 and ?? they are as defined in the formula () "), and where the compounds of the formula (I) where W is an oxygen atom at the beginning are obtained in variants a) c) sulfones idas (II), the background isocyanates (TV) and the chlorides of their bottom (VI) are novel compounds. In the same way, the invention relates to these compounds and their preparation. (rr) and (1/1) are preferably carried out under base catalysis in inert solvents, such as, for example, methyl chloride, acet oni tp Lo, dioxane or tetrahydrofurane, at temperatures of -10 °. Or up to the boiling point of the solvent in the jelly The bases that are used in the present are, for example, organic amine bases, such as 1, 0-diazadici cloTb .... 01-? Ndec ~ 7-ene (T) BU), in pari ular * in the case where P * is equal to fe i lo (substituted) (cf EP-ñ-44Rü 7), or tpinetii - ot riotí la minio, the last in particular in the case where R * - alkyl (cf., P-ñ-lftd 51b). The compounds (ie the formula (II) are obtained, for example, from N- (t ~ b? T? L) -sulphanicides of the formulas (VTII), (rx) and (X) (cf. formula VIII) *, Z * = R3NH-) ( Z = NHR (V I I I) Z '= NH2 (I X) LO Z' = N02 (X) Starting from the compounds of fopnuLa (VL11) where R, n, Rl, R2, 3 ui are as defined in the formula Ib (I), the compounds of the formula (II) are obtained by reaction with a strong acid. The possible fatty acids are, for example, mineral acids, such as either I-I2 SOA HOl, or strong acedoles. organic, such as ác? Jo t rd-J uoroace '1 co. I 1 t -butyl group is divided into t omporat u? at -20 ° C at 0 reflux temperature in particular of the reaction mixture, preferably at 0 ° C to 40 ° C, the reaction < * I can carry out in volume also in a solvent, such as, for example, chloride I put wood or chlorine. The compounds of the formula (VITD) are obtained, for example, from the aniline derivatives of the formula (IX) (cr. Form La (HIV), R * - NH2) by * reaction means with '. *'.

Suitable electrodes, such as, for example, anhydrous chlorides, anhydrides, isocyanates, t-cyanatos, sulphide chlorides, or amidosulphonyl chlorides (in this context, cf. ZabicL-y, "The Chernistry of" Anudes "b (Chemistry of the Finudas), pages 73-185, Interscíce, New Yod, 1970; F..3. Oorey and others., Retracted Lett. 1978, 1051; II.J. Saunders, R. J. Sloeornbe, Chein- Rev. 40, 203 (1948); S. OzaH, Ohem. Rev. 72, 457, ñ9 (1972); 0. Zolß, * zne? N. Forsch 33, 2 (1983); Houben-Uey -Hage ann, "I hoden der 1 Li prganichen Chemie "(M all of Organic Chemistry), 4th edi ion, Volume P.4, page _ *, B5 and sec", Thieine Vei lag Stuttgart, 1983;:. Golinsky, M "Mohasza, Synthesis 1970 , 823, Houboiv-Uey 1 - M? Ller "Me t hoden der orgaruschen Chemie" (Methods of Organic Chemistry), 4th edition, volume IX, pages 338-400 and 605-022, Ib Thierne Verlag Stuttgart, 1955; Houben-Wey 1-K1 armann, "l ethoden der orga ischen, Chemie" (Methods of Organic Chemistry), 4th edition, volume E "11/2, pages 1020-22," I bienio vOrlaq St > jttgar * t, 1985; S. Kpshna urt hey, letrahedron Let t. 23, 3315 (1982). ). The mentioned anilines (IX) are obtained by means of processes which are known from the literature, for example by means of reduction of the nitro groups of the compounds (X) (cf. formula (VITE), Z * - NO2), for example by catalytic hydrogenation or by means of reduction with iron in • > . a medium of acetic acid (in this context, cf .: H. Berpe, R. Meuhold, R. Sppng, 1 Ohem Soc. 1952, 2042; M. . reí fel de r, "Cataly? c Hydrogena ion in Organic Synthesis:, * ^ cedures and Coinrnentary" (Hi Catalytic drogenation in Organic Synthesis: Procedures and Commentary), J. Udey 8. Sons, New York (1970), chap. ). The compounds of the formula (X) can be obtained by means of nesting, starting from the benzoates of the formula (XI): ( (X I) (X i i) The formation of amide is carried out by reacting * the benzoates (XI) (alkyl R) with J? S ..? Nm: .s d < "> the formula (XI)., The compounds of the formula (XT) and (rr are mai-orlals of pair" la que known "-, of the literature or commercially obtainable (cf., for example, German patent application P 42 36 902.9), or the compounds can be prepared analogously for generally known processes., The amides of the formulas (HIV), (EX) and (X) are novel compounds. The invention relates to these compounds and their preparation, The following synthesis sequence, which is explained 2 / so forth to? i? l? ^? - the example of the compounds in which ,, - 0, offers an alternative access to the compounds (XI) (Ui = 0) Starting from the acids 2- not yet- nor trobenz.oi (XTT)), for example acid 2-a? n? no 4 - or trobenzo i co (XJIEa), the corresponding benzoic acid esters (XIV) (R ° - alkyl) are obtained by means of conventional icacíon with the alcohols cor espondient s ( R ° 0H) and an appropriate acid, such as, for example, H2 SOA.

R (X I I I) (X I V) The day of the motivation group and the reaction sub < , consistent with SO2 / CUCI2 obtains sulfate chloride (XV) (Analogous to Meerwein, Ohem, Per. 90 (1957) 341-852).

The compounds of the formula (XV) with t-butydarnine lead to the sulphonates of the formula (XE). The compounds of the formula (ITT) required for the reaction of the compounds (II ) according to the vanishing a) are known from the literature c, can be prepared 20 in accordance with known methods (cf, EP-A-70 804 or US-AM, 400, 101). The isocyanates of ferrous Isulfoni that of the formula (IV) can be prepared, for example, analogously to the processes of EP-fi-184 385 of the compounds of the formula (TT), for example with phosgene. The reaction of the compounds (IV) with the arnino-heterocyclic compounds of the formula (V) is preferably carried out in inert, aprotic solvents, such as, for example, dioxane, acet or triethyl or tetrahydro furan, at temperatures between 0 ° 0 and the point of boiling * of the solvento. The reaction of the sulfur chlorides (VE) with the compounds to my non-heterocyclics of the (V) and cyanates, such as sodium cyanate and potassium cyanate, is carried out, for example, in aprotic solvents, such as, for example, acetonitrile, if appropriate in the presence of bases, for example 0..5 to 2 equivalents of base, or in basic apr iodic solvents, at temperatures in e- L0 ° C and J00"O, preferably - L0 ° 0 and 60 ° C, in particular from 15 ° 0 to / 0 ° C. Possible bases or basic aprotic solvents are, for example, pipdin, pi-choline or lutidine. or one of these (see US-A-5,157,119) The (tio) isocyanates of La forula (VII) are obtainable by means of known procedures of the literature (EP-I-232067, EP-A 1665L6). .. The reaction of Los (t? o) isocyanates (VII) with compounds (II) is carried out from -10 ° 0 to 100 ° O, preferably 90 H I00 ° C, in a < • *, inert, aprotic, such as, for example, acetone or acetone, in the presence of a suitable base, for example N (C2Hs) 3 K2CO3-5 The salts (ie the compounds of the formula (I) are preferably prepared inert solvents, such as, for example, water, methanol, acetone, rnet chloride, 1 log, tet rahí ro urano, toluene or heptane, at temperatures from 0 to 100 ° C. Bases suitable for the preparation of the salts of The convention with the invention are, for example, alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkali metal hydroxides, such as NaOH, KOH and CaI OI-D2, arnonia or a base of suitable amine, such as t pet darní na or ethanoLamina. Acids suitable for training of salt are. for example, HC1, HBr, Ife SOA or HN 3. The "inert solvents" referred to in the variants of the previous procedure in each case mean solvents that < - or, inert under the particular reaction conditions, but are not required to be inert under any condition of reaction. The compounds of the formula (I) according to the invention, or salts of the same, have a herbicidal activity, ie, a lens against a broad spectrum of harmful plants of mono- and dicotdodon economically impotent before. The nr. Perennial plants that are difficult to combat and shoot of rhizomes, rhizomes, other permanent organs are also affected by means of active compounds.It is irrelevant in the 'sité if the substances are applied before sowing, (emergency or postemergence) Examples of some representatives of the mono- and dicotyledon flora that can be controlled by the compounds (according to the invention, can be specifically mentioned), without mentioning these proposed as a limitation to particular species. the delivery of monocot species of herbs, for example, species Avena, I oliu, Alopercui us, Phalaps, 10? ~ _ch? nochloa, Digi ria, Setaria and Oypor? s of the annual group and in?,? part of tropical species Agropyron, Oynodon, Imperita and Sorghuin and also Perytenian species of Oyperus are affected.In the case of di coi ledge species, the spectrum extends to such species as, for example, , Gali? M, Viola, Veronica, Larniurn, Stellapa, Aranton hus, Sinapis, Ipo oea, Hatp caria, Abutilon and Aids on the annual side and Convol vulus, Cirsiun, Rurnex v Artemisia ent r * e the perennial hires, Herbs occur under specific conditions of growth and rice, such as, for example, Sagí would give, Alisma, Fleochaps, Sci rp? S and Cyperus, are also surprisingly combated by active compounds LVOS of co fo t i nity with the invention. If the compounds according to the invention are applied to the surface of the soil before germination, the emergence of grass seeds is completely avoided, or the growth of herbs at the cotyledon stage,? or after they stop growing, and finally they die completely after three or four weeks have elapsed. When the active compounds are applied to the 5 green parts of the plants by means of the postemergence method, a drastic stoppage in growth in the same way occurs very fast after the treatment, and the plants remain in the growth stage that It exists at that time of the application. They do not die completely after a certain time, 10 so that the grass competition that is harmful in harvest plants is eliminated very early and always trusted in this way. Despite the fact that the compounds according to the invention have an oxidizing herbicidal activity against the herbs of mono- and dicotdedon, crop plants of economically unpopulated crops, such as, for example, wheat, barley, centono, rice, maize, sugar beet, starch and soybeans, are damaged only insi nificant entity or almost naña. For these reasons, the present compounds are particularly suitable for selectively oombat 11 the undesirable plant growth in crops of useful plants, The substances according to the invention furthermore have rogulatopas growth properties. ? ? soprendente in plan s of cultivation. They intervene through regulation in the endogenous plant mechanism and therefore can be used for specific influence of , plant attenuated and to facilitate harvest, for example by inducing desiccation and compressed growth. In addition, undesired vegetative growth inhibition and plant inhibition are also suitable, with no need to kill the plants. Inhibition of plant growth plays an important role in many mono- and "Lodon licoti crops, because the lodging therein can be reduced or avoided altogether. The compounds according to the invention can , used in the form of wettable powders, emulsifiable concentrates, spray solutions, powders or granules in the common formulations. The invention therefore relates to herbal and plant growth compositions comprising compounds of the formula (I) or salts thereof.

Ib The compounds of the formula (I) or salts thereof can be formulated in different ways, depending on the biological and / or physical chemical paters that exist, the possibilities of suitable formulation are, for example: powders or abi s (UP), powders so Lubi is in water (SP), concentrates water-soluble, emulsificant.es concentrates (EC), emulsions (LU), such as oil-in-water and oil-in-oil emulsions, spray solutions, suspension concentrates (SC), oil-based dispersions or water , solutions in oils, suspensions in caps? La (CS), powders (DP), 2b compost compositions, granules for application by means of dew and thiora spray, granules (OR) on the urine of the granules, spray granules, absorption granules and. adsorption rings, water dispersible granules (UG), water soluble granules (SG), ULV formulations, rock phosphate and ce r * as. These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kuchler, "Chernische Technologie" (Chemical Technology), volume 7, 0"Hausor * VerL.ag Munich, 4a. edition, 1986, Uade van Val enb? rg, "" Pesticide Fopnulat tons "(Pesticide Formulations), Marcel Ded-er, N.Y., 1973; K. Martens, "Spray üiying" Handbook, edition] 9 r "9, G. Ooodw in I. <d. I." The auxiliaries (necessary formulation, such as inert materials , surfactants, solvents and other additives, in the same way are known and are described for example, in: UaH-ms, "l-lannbool- 'of Tnse <doide Dust Dduo ?? t < * and Oar -pers "(Handbook (Dividing Vehicles and Dust Vehicles), 2nd edition, Darland Boos, Oaldwell NJ, 11. v" Oiμen, "I t roduct ion to Clay CoLleid Chenustry" ( Introduction to Clay Colloid Chemistry), 2nd Edition, JUiley 8 Sons, NY,., C. Marsden, "SoLvents Guide", 2nd edition, Enterscience, NY L963; "Deteigents and E ulsi f lers Annual "(Annual Detergents and Detergents) by McCutcheon, MC Publ. Corp., Ridgewood NJ;; Sisiey and Uood," Encyc Loped ia ol Surface Active Agents "(Encyclopedia of Agents. , Ohem Publ. Co. Inc., N.Y. 1964; Schonieldt, "Gren flachenal 't i-ve fithyl ene. X i daddul' te" (Adductions of Oxide of i, the Log of Agents Tensioning), Uiss. Verlagsgese J 1., S'uttgart 1976; Uinnacl-er-K? Chler, "Ohe ische rechnologie" (Chemical Technology), volume 7, C "Hauser Verlag Munich, 4th edition, 198b. Combinations with other substances that have a pestileidal accord, such as, for example, secticides, acaricides, other herbicides, fungicides, insurers, fortdizant.es and / or growth regulators, can also? IT will be prepared based on these formulations, for example in the urine of a finished formulation or as a tank mixture. Wettable powders are preparations that are uniformly dispersed in water and, in addition to the active compound, and a Ib inert substance or diluent, also comprises ionic and / or non-ionic natur'aieza surfactants (wetting agents, dispoi sant agents), for example alkylphenols pod ox leti sides, fatty alcohols? Or J i ox íet i sides , amine '*, polyoxyethylated fats, polyethylene glycol sulphides of alcohols or fatty acids, alkanesulphonates, to the amino acids, the sodium salt of acid 1 igru nsul foni co the sodium salt of acid 2 , 2 'dina fti Lrnetano- 6-6 -'- dis? L fomco, sodium salt of di bu da (talonsul phona oo also sodium salt of oleoil et d taup na "To prepare powders humee t bl For example, the active herbicidal compounds are finely ground in customary machines, such as hammer mills, chopper mills and air jet mills, and are mixed with / (xi ar-es) formulation at the same time or subsequently: emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example, butane, cyclohexanone, Lfor amide dir, xylene or any hydrocarbon or aromatic (he high boiling point no organic solvent mixtures, with the addition of one or more ionic surfactants and / or nonionic (ein? J sifi cant es.) E ulsif i can "is that they can be used, for example, the calcium salts of alkylaryl acids, such as dodeci lbencen ul [-on or Calcium, or soluble solvents, such as polyol fatty acid esters, ethers of lithium lipoprotein, glycol ethers of fatty alcohols, oxidizing products of propium oxide. / ox i (Jo de e deno, al quilpoliet es, sorbitan esters, such as for example you are of sorbic fatty acids, or are polyesterals, such as, for example, acid esters gi v - so Poli oxietlelensorbí tan "Powders are obtained by grinding the active compound with finely divided solids for example talc, natural clays, such as kaolin, bentomta and pirofdita, or earth d lat omace .. The suspension concentrates can be * on the basis of water or oil. They can be prepared, for example, by wet grinding by means of disposable bead mills and, if appropriate, by appropriate addition of surfactants such as, for example, those which have already been listed in detail. for other types of formulation. Emulsions can be prepared, for example, oil-in-water (EU) emulsions, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and, if appropriate, suitable surfactants such as for example those that were already listed in advance of other types of training. They can provide granules either by applying for *?. >; oers? on the active compound over the inert granular adsorbent or by applying the concentrates of the active compound, by means of adhesives-for example, polyvinyl alcohol, the sodium salt of polyacrylic acid or mineral oils to the surface of vehicles, such as sand, kaolinites, or inert granular material. Suitable active compounds can also be granulated in the umbilical form for the preparation of fertilizer granules - if it is processed, ie a mixture with ferrous liquors, as a rule, water-dispersible granules are prepared by the usual friction, such as spray drying, granulation, fluidized bed, granulation of pisca, mixed with high speed mixers, and extrusion without a solid inert material, Co or rule, the formulations agroquí ics comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of the active compound of formula (1) or salts of the same.

In wettable powders, the concentration of the active compound is, for example, approximately 10 to 90% by weight, the latter consisting of 100% by weight of constituents of the shaded formulation. In emulsifiable emulsions, the concentration of the active compound may be, for example, (L at 90, preferably from 5 to 00% by weight). Formulations in the form of powder comprise from 1 to 30, preferably 5 to 20% by weight. of active compound, and the solutions which can be subjected to spray drying comprise for example 0.05 to 0 IOL, preferably 2 to 50% by weight of the active compound. In • water dispersible granules, the content of the active compound depends partly on if the active compound is in liquid or solid form and in which ranching aids, fillers and the like is used, In the case of granules which are dispersed in water, the content of active compound is for example between 1 and 95% in Weight, preferably between 10 and 00% by weight In addition, the formulations of the active compound mentioned include, where appropriate, the particular adhesives or customary agents, wetting agents, dispersing agents, emul si fi cant is, agents of care, preservatives, anti-icon agents and solvents, redons, vehicles and coloring materials, anti-foaming agents, evaporation inhibitors and agents that influence pH and viscosity. 5 Combination couples that can be used for the active compounds according to the invention and 30 Mixture formulations or in a tank mixture are, for example, known active compounds such as described by * example in Ueed Research 26, 441-445 (1986), or "The Pest icide Manual" 9th Edition , The British Crop Protection b Council, 1990/91, Brac nell, England, and the literature cited therein. The following active compounds are mentioned, for example co or herbicides which are known from the literature and can be combined with the compounds (ie, the formula (T) (Note: the compounds are designated either with their "name O r-ornun "in accordance with the International Orga izat ion for andardizat ion (ISO) or by its chemical name, if appropriate together with a custom code number): acetocJor *; aci f luorfen, aclorufen, AKH 7080, that is * , acid rEl-l "5-r2-- chloro- 4 - (tpf" 1 uorornet? l) - pheno il -2 - ni t ro f eni 1] -2 5 rnet ox? et d íde] - arninolox i lacet Acidic acidic acidic acidic acidic acidic acidic acidic acidic acidic acid and acidic acidic acid or ammonium, amlophos, asuJa, atrazm, atoprop, barban, BAS 516, that is, 5-fl uoro-2-pheni 1 41-1-3-1, benzoxazin-4 -ona, bonazo Lm benf 1? oralin; benf? r-osato; 0 bensulfuron-methyl; bensulide; bentazone, benzof enap; benzo fluorine; I curl i] pro? -et i lo; ben t iazurona; biala fos; lufenox, brornac? 1; brornobut i da; bromo f enox a, brornoxind; liromuron; bu i na fos; busoxino a; butachlor; butamios; butenachlor; butidazole; butralin; butiLato; earbet amide; CDAA b that is, 2-chloro-N, N-di-pro? In? Lacetarm gives; CDED, it's going, 2-chloroal? L ester- of dietary acid i ldi t ocaí bam i co; COA 104927, that is, 2 - ["4-1" acid (5 cl gold -3 - f luoro-2 -pin di ni 1) - ex il , / ?? x 11 - p ro w ico y e te r 2 - p r ^ o p i n 111 co; c orne or x i te; c loramben; c: I oraz fop-buti 1 o, p? r? fenopbut but, cLorbrom? ron; chlorb? farn; chlorfenac; Lorf lurecolmet i lo; clone dazona; ethyl clopmurone; clomit rofen; cLorotoluron; chloroxuron; chlorprofam; c Lorsul furona; the ortal - dirnet do; c Lort lamí da; c mrnet il in: cinosui f? rona: cLotodim; clomazone; clomeprop; cloproxydim; Clopyraide; cyanazine; cycloate; cycloxydun; cycluron; ciperq? at; ciprazine; eiprazole; 2,4-DB; dalapon; -srnedifarn; from the fight; di-aLato; diearnba; diclobonil; (11 c 1 or rp i * op; dic 1 or op met 11 o; diet 111 o; di fe no xu ro na; di fenzoquat; diflufemcan; dnnefurona; diinet ador; dirnetamet quina; dimet zona; cyomazon; diinetipm; dimet rasul f uro na, c osuJ f ui ona; di ni < raini na; dinoseb; dinoterb; difenarnida; di propotpna; diquat; ditiopir; diuron; DNÜC, ethyl eglinazine; J 7, that is to say *, 5-c? Ano-l (1, 1 dunet dotil) N- ot d -3H -pi razol -4-carhoxauda; endotal; EP10; or rocarh; etal fl u ral irí; eta etsul fu ron - met i Lo; ot idnnurori; otiosin; etofurnesate; T5231, that is, N-r? -doro- ' - fl uoro - -l "4 - (3-f Luoropropy 1) - 4, 5 -? h? dro-5-oxo-1 H -tet r azol-1-113-feru L i -etanosul fonamide; F6285, is decn *, 1 -C5- (N -methylsul fond) -amino- 2,4-di chloro feni 11 -3-? net 11 -4- di fluorornet il-l, 2, 4- < pazol b ona; fenoprop; fenoxan, clomazon, fenoxap op -et i; fonuron; fla pr op-met Lio; flazasul f urone; fl azifop and ester derivatives thereof; f lucloral ní; f Lumetsu Larna; N r2, b - ii) uoro feni 13 -5 mtd - (1, 2, 4 - t paz.o loT 1, bal í r-?? (J i n- 2- < *,? i fonami da; flurnet urona; flumi proprietary; fluorodi phena; roroglui cofenet i lo; flupdone; fluroclop dona; flurox? p? r * a; f lura ona; fomosagen; fosamina; fup loxi feria; glu fos ato; glyphosate; halosatena; haLoxi fop and ester give fords of the same, hexaz ona, I lw 52, that is, N-- (2, 3 ~ d? chlor phenyl) -4- otox i met ox i) benzam i (la; imazaine tabenz - me tilo i marzap ir; irnazaqu a; nnazetarnetapira; imazetapi ra; irnazosul fu roña; loxinyl; isocar-bamide; isopropal ina; i soproturone; isourone; isoxaben; i soxapip f op; caibutdato; lactofen; lenacil; 10 ^ inurona; MCPA; MCPB, mecopro; mefenacet; rneduidida; inet a i trona; metazaolor; met abenz + azuron; rnetama; metazole; rnetodi phenone; rnet i] di mrona; rnetobroinur'ona; inotolacJor; me t o x u i * o n; met p b u i na; I do not? he was n-met; MI-I; rno 1 i na to; monkey! Going; diacid sulfate of rnonocarbamide, inonolinurone; l 5 onurona; MT 128, ie 6-chloro N- (3-cLoro- - μropeni 1) 5-rneti L -N- phen? L-1-p? Pdaz? namma MI 5950, that is, H-? 3 -c 1 gold - - (1-met? Letii) fon ill -2 - inet ilpent ana ida; naproan ili da; Ocí-'i-opa i Ha; Nama Lama; NC 310, that is, 4 - (?, - (L cJor-obenzoil) - J -metí 1 - 5 - be ció Loxipi razo la; no bu roña; nicos? L f urona; upi raclofen; mtraLina; nor trofen; nitor 1 uorien; norf 1 urazoa; oi bencarb; opxaline; oxadiazone; oxyfluor * fen; paiaq? at; pebble pendunetal ma; por-f 1 ui dona; fenmedLi m; fonisofa, fen edipam; piclora a; pipero fos; icarb piribut; pin feno-butdo; f > ret? lac; l? r; '. *' P p rn i su 1 f u i -on et 11 o; p roe the z i na; | ) rí i a i na; p ro f 1 u r * a 1 i na; ? r * ogi mazi na-et 11 o; prometori; prornet r *? na firopaclor *; prof propaquizafo and esters derived1 *, of the same; propazma, μ jfam, propizarnide; pr * osul al? na; prosul foearb; ppnaclor; ?? reason! I kill, ?? reasons pi razosul furo eti lo; pyrazoxy on; pip ato; quinclorac; qummerac; quinofop and esters derived from them, perhaps, and ester derived from the same; (| uazalofo-et i lo; q? izalo fo-pt e fup lo; renri duron; dnnron; S 275 that is, 2-r4-chloro-fluoro-5 - (2-propirn loxi) -ren? l 4 , b, 6,7-tetrahydro-2H-? r? dazoi; S 482 that is, 2- \ 7-fj uo o- 3, 4 -di hi (J? o-3-oxo -4- (2-pro ini 1) 211-1, 4-benzoxazo n-b-i 3 -4, 5, b, 7 -te rahydro-1H-iso indo i 1, 3- (2H) -dione, secbuineton; setox Ldima; siduron; simazine; symmethrin; SN 106279, ie, aci do 2-CC7-f 2-chloro-4-tpf luor-omethyl) -phenoxa-2 -na ft dlox 1 -propanoic and stor * methyl; s? l fometuron-met i lo; sulfazurona; f lazasul f urona; TCA; tebutarn; tebutiuron; terbacil; * erb? carp; terbuclor; terbumeton; terbut i lazi na; terl &utt; < reads, N, N - di and i] - 2 - T 2 -e 111 - 6 -me ti 1 f-eru 1) - su 1 f on i 13 1 ll-1, 2,4-triazole l-carboxam gives; t? azaf lurona; 11 f ensul f uronted; t > boric b; t? ocar * baz? the; t raLcoxi dune; *? - lato; tr iasul furona; t pazo f enamida; t r ibenuronmate; tpcLopir; tpdifana: t ri etazina; < p f lure 11 na; t pmeturone; vernolate; Ul 110547, that is, 5 ~ phenoxy i-1 -f3 - (tp f 1 uoro et d) fond3-lH-tet razo l. To be used, the present formulations in the commercially available form, are used in a customary manner, if appropriate, for example by means of water in the case of wettable powders, emulsifiable concentrates, dispersions and dispersible liquids in water, and then apply to the j, such parts of vegetables, or soil over which the plants are or in which they grow or are present as seeds and which are used in agriculture or industry. soil granules and granules will be dispersed, and spray solutions are not usually diluted additionally with substances that are useful in the application of the required amount. (I) J >; be applied, it varies according to the external conditions, * Aies as temperature, humidity and nature of the herbicide used, among other things. I can vary within (it increases the limits, for example between 0.00J and 10.0 g / ha or more of active substance, but it is preferably 0.005 and 5.0 g / ha. fl. Chemical examples < -., '2 -Amino- 4 - i trobenzoat or meth i lo. A mixture of LJ8.8 g of anhydrous-4-nitrobenzoic acid, 1000 ml of methanol and 120 mJ of concentrated sulphuric acid was added to the flask for 16 hours. The mixture is concentrated under reduced pressure, the residue is t > Acetate in ethyl acetate and wash the mixture with saturated NaHCO3 solution, after drying * over Na2 SO4, the organic lase is concentrated, thus obtaining 114.2 g (89%). nor methyl t-benzoate, with a melting point (? .f "of 156-158 ° C), methyl 2-chlorosulphonyl-4-methylbenzoate, a solution of 122.3 g of sodium nitrite ori 180 ml of water in the form of drops to a suspension of 1300 ml of glacial acetic acid, 516 ml of concentrated hydrochloric acid and 441.7 g (1,689 moles) of 2-a? n? no-4-n? methyl t-benzoate (example a) at a temperature between 13 and J5 ° C.

After stirring this reaction mixture for 30 minutes, it is added as drops to a solution, saturated?; On SÜ2, of? ? g of copper chloride (TE) and 1300 ml of glacial acetic acid at approximately 26 ° C. When the evolution of gas ends, the mixture is poured onto ice / water and the chloride of the bottom which precipitates is filtered with suction and then javaged with water to give, after drying, 354.3 g of 2-chloro-sul fond-4- ni tro-benzo to (Je methyl, mp 08-90 ° O. o) N-er-but d -2 met oxycarboni 1- 5-n? t ro-bencensul fo ami da »260 g of ter-but! It was then added dropwise to a solution of 384 g of 2-c 1 or'osul f on i L -4 and methyl trobenzoate (example b) in 1500 ml of ethyl acetate at 0 ° C. The reaction mixture is allowed to warm to room temperature and is stirred at this temperature for 1 hour. After washing * with dilute hydrochloric acid and water, the organic phase was dried over MgSO * and concentrated. The residue is extracted by stirring with diisopropyl ether. Performance of the < *, uJ phona ida: 377.6 g; p.f. L22-L24 ° C "d) - er-bu? -2 -dimet i 1 aminocarboru 1 - 5 - nitro cv nzos? L fonamide» 115 g of N-t er-but d - 2 ~ are saturated with gas rne t oxycarbonyl 5-nitrobenzene L fonarní da (example o) in 1500 i ethanol with approximately? 200 g of dirnet i lamina. The mixture is stirred at about 35 ° 0 for one week., The solution is concentrated under reduced pressure, the residue is taken up in ethyl acetate and the mixture is washed successively with acid, dried or saturated MaH003 solution. and a solution of NaCl. After drying over MgSOz,, the organic phase is concentrated. We get 92 g I n N-t er-but i i -2 -di I put in the nocarbonyl-5-it o-bencons: fonami da: p. F. 130-14 L ° 0. e) 5-fim? no-N-t or-but i L 2 di met i 1 d.ninocarbon d benzenesu 1 fonami da. 23.6 g of zinc powder are added to a suspension of 22.0 g of Nt er-bu i 1 -2 -direnet and 1 ami noca r * bo i 1 - 5 - u tr * o -benoonsuJ phonainide (example <J) , L8.2.2 g of ammonium chloride, 0.25 g, and 150 g of methanol. The mixture is then stirred at 50 ° C. When the reaction has ended, the sun is filtered. After washing the solid with ethyl acetate, the filtrate is concentrated, the residue is taken up with ethyl acetate and the mixture is washed with water, after drying over MgSO *, the organic phase is concentrated and the The residue is washed with (Isopropyl ether: 17.5 g, pp. 205-208 ° C, f) N-ter-butii -2 d unet danunoeai bon i 1 b-met oi carboulami nobencensul fona i da ..

Add 0.47 g of chloroform of methion in drops to a suspension of 150 g of 5-ammo-Ni er-butii-2-di.net i] ami no ca bón 11-bencensul fonamide (example e) and 1.46 g of NaCHÜ3 in 50 ml of OH3CN at 0 ° C. When the reaction is complete, the reaction mixture is converted to ethyl acetate and The reaction is washed with IN hydrochloric acid, dried over MgSO 4, and concentrated. In this way, 1.48 g of N-t er * but? -l-2-dimeti lamí noca rboni 1- 5- et 0 1 carhonilami no-benzenesul fonam 1 da; mp 18 ° -108 ° C. s > N-tert-butyl-2-dιnenet ocarb 1111 -5- 1 orrn L 1 aini obencensul fonamide A mixture of 0.34 ml of thermal acid and 0.70 ml is heated. i of acetic anhydride at 50 ° 0 for 2 hours, and a solution of 0..B5 g of 5-amino- N- tor -but 11 -2 -dnnet ilarní nocarbon 1 Ibencensulfon ida (example o) is added. and 3.5 mi do dimet 11 fonnamida (MF "). After 4 hours, the mixture is taken up in ethyl acetate and washed successively with dilute anhydrous acid and saturated Nal IOO 3 solution. After drying over the MgSO 4 and concentration of the organic phase, 0.80 g of a highly viscous substance that is used in subsequent reactions without further purification (example J). h) N-1 er-but 11-2 - nnet ilanu noc rboni L 5 - rop io i l no-benzens? fonam 1 d. 0.85 g of 5-arnino-N- t er- but d 2 di inet i laininocarboni i-benzene? Lonamide (example e) are dissolved in 3.5 ml of DMF 0 °, and 0.20 g of propylmethyl chloride are added thereto. and O. ', 0 mi de t pei i lamí na ,. After the mixture is stirred at 5 ° 0 for 1 hour, it is taken in ethyl acetate and washed successively with dilute hydrochloric acid and water, after drying the mixture over MgSO and concentrating the organic phase, the < Le in 0.60 g of a highly viscous substance Which is used in subsequent reactions without further purification (Example I). i) 2 - (Jirne ti la íca nca rbo i 1 -b -, "* otox? carbonj 1 ami nobeiicens? 1 fonam ida 1.40 g (Je N-tert-buti L-2-di inet i Lamí no carbo ni L -5-? Netox? Ca bón i larri i nobencens? L fonam ia ( example f) in 25 mL of acid tr *? r 1 uoroaeet co (for 18 hours, after which the acid has been added, the residue is suspended in toluene, the renewed concentration gives 1.40 g (He su la! fona i da; p, .f. 75-¡7 ° C. j) 2 - Dirnet i la nocar boni 1 5- f opni 1 ami no React 0.85 g (Je N-ter-buti) - 2 -di me ti 1 arni no -carbo 11 -5- f or ila o-bencens? l fonaini da g) with 10 ml of acid tpf luoroacet i co analogously to example t) .. 0.08 g of a highly viscous mass is obtained which is used ori the reaction described under the example m in puri fi cation adi ci ona 1 .. k) 2-D? I licked nocarboni 1 - 5 - propí ol ami no hencens? L f? Nami da .. kf 0.80 g of Nt er -butyl- 2- n-γ-lamino-car-boni-5-pr-opionyl arnino-benzenesul-fonapuda are reacted with 10 ml of t-fluoroacetic acid analogously to Example 1. 0.80 g of a highly viscous mass which is used in the reaction described under example n without further purification. 1) N ~ C4, 6 - dimet ox ipi rirnid - 2- 11 -airn no carbon i 13- 2 dirnet 11 -ammocarboni J - 5-rnetox? Carboru larn obencensul fo ami < -\to. (see example 53 of table 1) "10 - DUU is added to a suspension of 1.40 g of 2- di eti laminocarboni 1-5 -rnetox i car-boni laminobenzene fonany (example i) and 1.28 g of 4 , 6-d? Netox? 2 - phenoxycarbo d atn i no- pirippdina in 30 ml of CH3CN at 0 ° O. then the temperature is allowed to increase slowly (Je reaction to the teinperature ui a environment ?. After the solvent is distilled off, the residue is taken up in water and the mixture is washed with diethyl ether, then acidifying the aqueous phase with concentrated hydrochloric acid, which is separated from it. wash with methylene and ether di 1 sopr-opy li co and then dry. Yield: L.45 g as a colorless solid of p. f. L81-182 ° C (decomposition) ,. ) N-r 4, 6 -dirnetoxipi nm? Dn-2-LL) -ammoca boni 13-2-dnnet 1 the nocarbom 1 -5-fopni laminobenzene phona ida. (see example 0 of table 1). 0.88 g of 2 -dirnet 11 arn moc r-borní - 'are reacted. I- 5- fopni l -ami nobencensul fonarruda (example j) with 0.89 g of 4, b- dunetox 1 - 2-phenoxycarboni Lammopí pmi dina and 0.98 g of DBU in 10 i of CH3CN, ana Logarnente to example 1). 0.69 g of 1 1 sulphide 1 crystalline urea with mp ": 126 ~ 127 ° C (decomposition) n) N- [4,6-d? Netox? P? P my din-2-il) - arn 1110 carbo ni 13 -2- dimet L Lamí nocarboru 1- 5 - propiom Jaini no-benzenesul fonamide b (see example 22 of table 1)., React 0.80 g of 2 ~ dimet.darn? Nocar * bon? L -? Rop? Ia mohoncensulfona? N? Da with 0.74 g of 4, 6-d? Metox? -2- renoxicar-bonilainino-pir-irní dina and 0.82 g of DBU in 10 ml of OII3CN analogously to example 1). 0.68 g of the crystalline O. ui fonilurea are obtained with mp: 135-14 L) ° C (decomposition). o) Salt (Je sodium d €? NC 4, 6- d unetox 1 ?? p mi d 1 n ~ 2 - 11) - ai nocarbonyl] - 2-d ?? net 1 lainmocarbonyl -5 - inet ox ica r * pump the no-benz: ens? l fonami ^ \ a "(see example 21 of table 2) 5 1.85 ml of 1N sodium hydroxide solution is stirred into a mixture of 0.93 g of N-T (4 - dnnet ox 1? p my din- 2 - 11) -ai nocarboni 1 2 - di inet 1 lamí noca rbom 1 5 m * - * -.x 1 carboni lamí rio benzenesuL phona ia in 20 ml of OH3ON ..

After a clear solution is formed, the mixture is concentrated or reduced pressure. 1: 1 The residue is stirred with a solution of ether di sopropyl. Thus 0..02 g of the salt are obtained with p. f: 187-191 ° 0 (decomposition) .. p) Sodium salt of N-C, 6-di ethoxy ?? p i di n- - 11) ami nocarboru 13- -d ?? net ilaminocarbonil -5-fopni lamino bencensul f onam 1 da., see p e e 1 p o io d 2). 0.30 g of NT, 6- (|, ne or? Irin d -2 -d) -arm no carbo or 13- -dirnet ilarni ocar-boni L-5 formdaminobencerisul ronamide (example) and 0.65 mL of solution are reacted. of hydroxy or sodium in 4 ml of methanol and 4 ml of 5 CI-I2Cl2, analogously to example o). 0.32 g of the s l are obtained; p. f,: 205 ° C (decomposition) ,. q) Sodium salt of N-T (4, B-dpnetoxy-ri i din-2-yl) - aini nocarbon? p-2-? net 1 Laininocarborul- 5 -propioni l í no-bencensul fonam 1 da. LOidea and example 12 of table 2)., React 0.30 g of NL (4,6-d 1 me tox 1 ?? rimi dm-2 -1 L) -am mocar bom 13-2 - di mot 1 l mmoc bo i 1 5- pi'opí oni laminobenzensui fonarní da (example n) and 0.60 ml of sodium hydroxide solution in 4 ml of methane L and 4 inL of? Í5 CI-I2CJ2, analogously to example o). 0.31 g of the salt are thus obtained; p. f.- 212 ° C (decomposition). The compounds described in the following Table 1 are (according to the previous examples 1) .-. n) or of foi ina an loga; the compounds described in the following table are obtained according to Examples o) to q) or ana Legamente.

! Abbreviation f. - melting point T t - ethyl Me - inet do Pr * = «Pr - n - propiLo i pr - io ropilo c i - ciclopropdo li u = n lu - n - but iio i Bu - i sobut i Lo -A Bu = t - buti Lo T'h - phenyl . 1. CUñDRQ 1 Table 1: compound of formula (la) f.2 . J Table 2: Compounds of formula (Ib) fifty V Formulation examples. ) e obtains a powder composition by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of the liquid, such as the inert substance, and stirring the mixture in an impact mold. ^ c, ° obtains a wettable powder easily dissolved in water by mixing 5 parts by weight of a compound of the formula (I), 64 parts by weight of quartz containing kaolin as the inert substance, 10 parts by weight of the mixture. at 50 acid potassium 1 igni 1 sulphonic acid and 1 part by weight of the sodium salt of olea Irneti taurine, with the wetting and dispersing agent, and grinding the mixture in a spinneret disk mill. 5 c) A dispersion concentrate is obtained which is f-acylient dispersible in water by mixing 20 parts by weight of a compound of formula (T) with 6 parts by weight of ether of the alkyl phenol-poly glycol (R Tp- ton X 207), 3 parts by weight of the ether of i sot ri decanol-poi i gJ icol (8 moles of etiLeno oxide) '* • 71 parts by weight of physical mineral oil (scale of use, for example, approximately 255 to above 277 ° C), and grinding the mixture to a fineness of less than 5 microns in one milliliters of friction. d) A syrupy concentration of J5 parts by weight of a compound of the formula (E), 75 parts by weight of the lohexanone, as the solvent, and 10 parts by weight of the nonyl phenol oxotylate is obtained. , as emul si (i cant e "'"' '- Digestible granules are obtained in water by mixing 75 parts by weight of a compound of formula (1), 10 parts by 0 weight of calcium salt of acid ignx of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 1 and 7 parts by weight of kaolin, milling the mixture on a disk mill and granulating the powder in a fluidized bed by spraying in water as the liquid of granulation., t) Also obtainable digestible granules in water I nornogenerated and pret rred 25 parts by weight of a tax of formula (T), 5 parts by weight of the sodium l, of 2,2 'dina ft and methane-5,6' -disulfonate. 2 parts by weight of the sodium salt of oleoylmethyl taurine, 1 part by weight of polyvinyl alcohol or 1 ico, 17 parts by weight of calcium carbonate and 50 parts by weight of water in a colloidal mill, subsequently grinding the mixture in a ball mill and atomizing and drying the resulting suspension in a spray tower by means of a single substance nozzle. ' Biological Examples 1. Action Herbicide, pre-e? Nergenc? A. Seeds or rhizome pieces of mono- and dicotyledonous weed plants were planted in sandy loam soil in plastic pots and covered with soil. The compounds according to the invention, formulated in the form of wettable powders or emulsion concentrates, were then applied to the surface of the tiered cover as a suspension,? sa or emulsion in different doses, with a quantity of water applied, when it is converted, from 600 to 800 l ^ ha. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions? Ar * to the weeds. [-11 damage to the plant or emergency damage was assessed visually after the emergence of the plants axis tested after a trial period of three to four weeks, compared with controls without treatment. As the results of the tests show, the compounds of hl according to the invention show a good pre-activity. herbicide urgency against a broad spectrum of grass weeds and large foliage axis weeds. For example, the compounds of Examples 8, 15, 22, 25, 30, 40, 44, 53, 58, 59, 65, 72, 77, 87, 115 and 116 of Table 1 and the compounds of the examples 1, 7, 12, 16, 17, 20, 21, 22, 26, 28-30 and 32-35 of Table 2 have a very good herbicidal action against harmful plants such as Sinapis alba, Chrysant hemu segetum, Avena sativa, St the average wool, niopeeurus yosuroides and Loliurn uí t it lo ruin, "" .. ..jen apply in pre-emergency in an amount of 0.3 g and less active substance per hectare. 2. Action Her cide, post-emergence Seeds or pieces of rhizome of pLant s of mono- and dicotyledonous weeds were planted in the sandy loam in plastic axis pots, covered with soil and developed in a good or good inventory. Growing conditions .. Three weeks after sowing, the test plants were formulated as wettable powders or as condensation compounds in accordance with the invention. emulsi, were applied by sprinkling on green deliveries of plants in different doses with an amount of water applied, when converted, from 600 to 000 l / ha, and after that the test plants have remained in a for approximately 3 to 4 weeks under conditions of growth, the action of the preparations was evaluated as compared to controls without treatment. The inventories according to the invention also show a good activity. rbicide against a broad spectrum of economically important broadleaf weeds and broadleaved weeds when applied in post-emergencies. For example, The compounds of examples 8, 15, 22, 25, 30, 40, 44, 53, 55, 58, 50, 65, 72, 17, 8, 115 and 116, of Table 1 and the compounds of examples 1, 7, L2, 16, 17, 20, 21, 22, 26, 28-30 and 32-35 in Table 2 have a very good action »? Skilful against harmful plants such as Smapis alba, Stellapa inedia, Alopecurus myosuroides and Lolium ult Lf lorum, (.hrysanthernum segeturn and Avena sativa, quack is applied in post-emergence in an amount of 0.3 kg or less of active substance per nectarea. Tolerance of the harvest plant I additional tests in a greenhouse, seeds of a relatively large number of plants were planted t * 'harvest and weeds, on sandy, sandy ground and covered with earth. Some pots were tied immediately as described in Section L, and the others were placed in a greenhouse until the plants developed two to three green leaves, then sprayed with the substances of the formula T axis conformed to the invention and in different doses as described under section 2. After four to five weeks of the application and the time of stay in the greenhouse c * e found, by means of visual evaluation, that the compounds coni orm to the In this invention, they left the harvest chains, such as soybean, cotton, turnip, beet, and potatoes, without damage, both in pre and post-emergency, even in the presence of high levels of active compound. Some substances also retained even the harvest grasses, such as for example cebaela, wheat, rye, sorghum / my or, corn or rice. The compounds of formula I have a high qualectic selectivity in this way to combat plant growth. undesirable in agricultural crops.

Claims (2)

1. NOVELTY OF THE INVENTION CLAIMS A compound formula (T) or a salt thereof wherein U * is an oxygen or sulfur atom, IJ2 or an oxygen or sulfur atom, n is 0, 1, 2, or 3, R is halogen, alkyl or Alkoxy, independently of substituents R n is greater * L axis; R 1 is hydrogen or a substituted or unsubstituted hydrocarbon or a hydrocarbon radical; R2 is hydrogen or an unsubstituted or substi tuted hydrocarbon r, or the NR1R2 group or a heterocyclic ring has 3 to 0 20 atoms of ring, which is substituted or unsubstituted and contains the N-ring of the H 1 R group or a hetero-to-Lo ring and may also contain additional nitrogen atoms; R3 a radical acyl; R * is hydrogen or an alphatic hydrocarbon radical; X. And they are dependently : > halogen, Ci-C-alkyl, alkoxy, or Ci-Cß alkylate, wherein each of the last 3 radicals mentioned is substi tuted or unsubstituted by one or more of the This group consists of the halogen, the C1-4 coxy and the Ci-0 alkyl 10, the C3-e o-cloalkyl, the 2-C.6 alkenyl, the C2-C e alkolem, the alkoxyloxy C3 -Ce or C2 -Ce alkynyloxy, and Z is CH or N. 2. A compound or a salt thereof according to claim 1, characterized in that, R1 is ll or alkyl, alchem Lo, alkyloxy, alkoxy, alkenoxy, alkynoxy, heavenly, cycloalkyl or phenyl, where each of the radicals mentioned above is substituted or unsubstituted and contains a total of up to 2k carbon lathes; R2 s H or alkyl, alkenyl, or alkyl, wherein each of the three radicals mentioned above is substituted or unsubstituted and contains a total of up to 24 carbon atoms, or the group NR1 R2 is a ring The substituted or non-subsituted tetracyclic ele- or 4-R athemo-axis ring, where the group contains a total of up to 10 carbon atoms; R3 is acilo or '* he has up to 24 athemos fell to him, and \ V * is II or to uilo, aJo ilo, alcjum 1 lo, where each of the three radicals mentioned in the last contains up to 12 atheists carbon. 1. A compound or salt thereof according to claim 2, characterized in that * is II, alkyl C1-C12 axis, alejuenil axis C2-C12, alkylo C2-C12. C 1 -C 12 alkoxy, C 2 -C 12 alkenoxy, 2-12 alkynoxy, cycloalkyl O 3 -Ce or cyclohexy O 5 -Ce, wherein each of the eight radicals mentioned in the latter is substi tuted b or unsubstituted, by one or more radicals of the group that halogen, cyano, acid, C0-R5. 0R6 NR? H.H . R9, 50-RIO and SO2-R11, or substituted or unsubstituted phenyl; R2 is H, C1-C12 alkyl, C2-C12 alkemyl or C2-C12 alkynyl, where each axis the radicals mentioned above is substituted or unsubstituted, by one or more adLas of the group consisting of axis Halogen, cyano, azide, C0R12 0RI3, NR14R1S, 16, S0-R17 and SO2 -R18, or the group NRi R2 is a hete er * oc? cl? co of /. to 8 ring atoms, which may contain "" "" --.st to 2 axes het ero-am 1 the ational in the ring group consisting of N, 0 and S and is not substi tuted or is replaced by one or more radicals ejel group consisting of allogenous axis, alkyl Ci-Ce axis, NO2, N3 V CM; R3 is C0-R19, CS-R20 t SO2-R21, S0-R21 or 0 (-NR2i) -Ri9-R4 is H, C1-C3 alkyl, rtl < C s C or C2 -Cs alkynyl; R5 is H, Ci-Cs alkyl, C2-C5-alkenyl, C2-C5-ajinokyl, C1-C5-alkoxy, C2-C5-alkenoxy, C2-C5-alkyloxy, NR22R23 (> OJ-I) R6,. > < - • | - | and < á 'u'? Lo of Ci -Cs, haloal quilo do Ci-C5, LqueniLo of C2-C5, haLo 1 uen Lo de C-Cs, aLquiniLo de C2-C5 or baloalkyl 11 or of (.2 C5; R7 is H, alejuyl, Ci-C5 axis, C2-C5-alkenyl, C2-Cs alkyne Lo, Ci-Cs, 00 CH3, or COOCH3; R8 is II, to the quilo ele Ci-Cß, alchemlo axis C2 -Cs or alkyi of 2 -5; or the group N 7R8 ?? A heterocyclic ring of 4 to 8 atoms may ring, and may contain up to 2 ele atoms -ani 11 or more in the ring of the quo group consisting of | \ |. 0 and S and is substitute or not substi tuted by one or more radicals «Jel group« | ue consisting of halogen, alkyl Ci-C axis, NO2, N3 and CN, R9 is H, alkyl C1-C5, at «juemlo C2-C5 alkynyl, C2-CS alkynyl, haloaltjuyl C1-C5 axis, C2-C5 haloalkyl, or haloalkyl chloride of C2-C5, Rio is C1-O5 alkyl. C2-C5 alkenyl, C2-C5 alkylaryl, C1-C5 haloalkyl, C2-C5 haloalkanyl or haloalkyl or C2-Cs, H is C5-C5 alkyl, C2-C5 alkoxy, C2 alkynyl -Cs, C1-C5 haloaldehyde, C2-C5 haloalkyl, haloalkyl or C2-O5, coxy alkyl of Ci -Os, cycloalkyl of (.3 Ce or cycloalkylene or C5-C8, R'12 is a Radical ana Logo to "& '. R13 os a r * ael? cal analogous to Rß; Ri? is a r-anical analogue to I ??; RI5 is a radical analogous to Rß, or the group R ^ Ri ^ It is a group analogous to NR7R8, Rie is a radical analogous to R9, 17 is a radical analogous to Rio, Rie (> an analogue to RH, is H, C1-C12 alkyl, alyl of O2 -C12, C1-C12alkoxy, alkylthioCiCl -O12, O-1,2-O-1,2-alkyanoxy, C2-C12-aluinoxy, cycloalkyl, O3-Cs, chloric-acid «jueni lo« le-Ce, alq? I The word "1e Ci -O12, dial qui i aini o de C \ s,? J COX I 11- OÍ - 1 qui 1 nini no-N-í * C4, where each of the 13 radicals mentioned at the bottom are substi- tuted or not substi tuted by * one or more radicals of the group ejue consists of allogeneic, cyano, ai do, 00- R2¿, 0R25, R26R27, R28, S0R29 and SO2R30, or a substitute it or not subs itui, phenoxy or phenylamino radical; 20 a radical analogous to R 9; R2i is a L radical analogous to RH; R22 s H, Ci-C5 alejuyl, C2-C5 alkenyl, alkynyl of O2-O5, Ci -Os alkoxy, C2-O5 alkenoxy or alkyloxy O2-C5 alkoxy, in «Where« to one of the 6 radicals? Nenc? Ona «the last 08 rs subst ituLdo or not subst itui or, by one or more radicals of the, ru? < > which consists of allogen, cyano, azido, arnino, mono- and disubstido, Ci-C3 alkyl, Ci-C3 alkoxy, Ci -3 cyt Isul, Ci Ci3 and alkyl + 10 O1 -C3; R23 is H, to the Ci-C, alkenyl of C2-C5, C2-C5 alkoxy, O-Cs alkoxy or C2-C5 alkanoxy, wherein each of The 5 radicals mentioned above are substi- tuted or not substituted by one or more radicals of the group consisting of allogen, cyano, aio, amino, mono- and? substituted, C1-C3 alkoxy, Ci -O3 alejuylthio, C1-C3 -alkyl and the ejuyl sul fl ru The Ci -O3 axis; or the group NR22R23 s an heterocyclic ring analogous to NR? R8, preferably a ring of 5 or 6 ring atoms, which may contain up to 2 ring "Je hetero-am 11 or additional ring in the ring" group which consists of N, O and S and is subsumed or unsubstituted by * one or more radicals of the group consisting of geno and alkyl O1-C4, is H, .. What is C1-C3, alkoxy t Ci- O3, NH2 or mono mono -o di subst tu? «Lo; 2S w H, alkyl of Ci-O5, alkanoyl of O 2 -Cs, to the jum io of (.2 Os, hloalejui lo ele Cs, haloalíjueni that of C2 - Cs, or haloal qui rulo ele C2-C5; "26 e II, alkyl ele Cj. -C3, Ci-C3 alkoxy, CO-CI-I3 or CO-H; R27 is H, alkyl O1 O3; or the group MR26-R27 s? n group «1e analogous to NR22R23; R28 e | - | alkyl C 1 -C 3, haloalkyl C 1 -C 3, nitrile C 2 Os, haloalkyl, C 2 -C 5, C 2 -O 2 or haloalkyl, C 2 O 2 -Os; R29 is alkyl of O (.5, haloalkyl of O1-O5, O2 Os alkenyl, C2-C5 haloalicylic acid, C2-C5 or haloaltjuinyl «1e C2-Cs; R30 is an analogue to R2, and X, Y an 1 nde? In «1? Ently between itself allogeneic, Ci-C4 alkyl, Ci-Ci coxi or alkyl ti oe Ci-Ci, where each One of the 3 radicals mentioned in the last one is substituted or not substituted by one or more radicals of the group consisting of halogen, alkoxy "C" -C "and alkylthio of C1-O4, or anno-rnono- or dia-C1-alkyl. C4, C3-C6 cycloalkyl, alchemyl "Je C3-C5 or C3-C5 alkyloxyL, 4.- A compound or a salt of the same confopni" Jad "- in any of claims 1 to 3, characterized in that the group NHR3 on the ring of phen 1 is in the meta position in relation to the group SO2 and in the position para in relation to the group CLJ -MR-R2, and in which H is? n oxygen atom, (2 is an oxygen atom, n is 0, Rl is II, C1-C4 alkyl, alkoxy, or Ci -O2 or femlo, which is substi- tuted or not subsumed by one or more radicals of the group.; | ue cons ti.) "Je hal geno, Ci-C2 alkyl, < lco x? de Oí -O2, lialoalqui lo «Ci C and Ci-C2 haloalkoxy; R2 to H, alkyl of C-O2 or alkoxy of O1-C2; or the group NR1R2 is a heteric ring 1 with 5 ring atoms "which contains up to one atom of additional ring on the ring of the group consisting of N and 0 and is substituted or not substituted by one or more radicals of the group "jo consis e of alkyl of O 1 -C 2; R3 is 00- RI9, 0S-R20 or SO2-R21, A H or 0H3; i9 is H, alkyl "Je Ci-0", alkenyl? O-0,4, alkynyl "O 2 -C", lcoxy "le (. 1 -C 4, alkyl O-Ci axis, alkenoxy O 2 -Ci axis, O 2 -C -alkyloxy <4, cycloa l < | u? C3 - &, alky the «Je Ci-Ci ,, d? al < ju? la? n? no of O1-O4, alkoxy of N -, \ -C2- It is not the case of M-Ci-C2, where each of the ten radicals mentioned at the end is sub- stituted or not substituted by one or more radicals of the group consisting of halogen and carbon dioxide. C?; Or a lemlo or phenox 1, which is substituted or not substi tuted by * radicals of the group of halide, alejuyl ele C1-C2, alkoxy of C1-C2, haloalkyl of Ci-C2 and haloalkoxy of I heard -C2, R20 is a radical analogous to R9, and R2i is alkyl "OI-O3, hal lyl of Ci -O3 or alkoxy of C1-C3 -" -, chyl of Ci-C2; radicals Y and X is halogen, C1-C2 alkyl, C1-C2 alkoxy, C1-C4 alkoxy, wherein each of the radicals mentioned is substituted or not substituted by one or more radicals. is "The group consisting of halogen, alkoxy of O-C2-V alkyl-10 of C1-C2, or mono- or dialkyl-1-amino-C1-C2; V © 1 other of the radicals Y and X is alkyl O1-O2, haloalkyl Ci -O2. Ci -O2 alkoxy, haloalkoxy of (.1 O2 or alkylthio of C1-O2; and Z is CU or N. 5.- A process par * to the preparation a compound of formula (T) or a salt of the same according to one of claims 1 to 4, characterized in that it comprises a) reacting a compound of the formula (ID) with a cai bamato het erocicli co of the fopnula (III) in the "Je R *" is faith or alkyl or substituted O1-C4 or not subst 1 t? ido; or b) reacting a 1 soc 1 anato of sul foril the formula (IV) with a hydrochloric amine of the formula (V) Y or c) make an effluent sulfonyl chloride (VD 7? with a heterocyclic amine of the above formula (V) in the presence of a cyanate, or cl) reacting a sulphone of the above formula (II) with an (JO) isocyanate of the 1U formula (VID in the presence of a base n "Jecua" Ja, "as, for example, (potassium fonate or laugh * i lamí na; where, in the previous formulas (II) to (VII), the radicals R, R.sub.1, R.sub.2, R.sub.3, R.sub.1, and I.sub.
2. 2, X, Y and Z and n are as defined in formula (1), and wherein the compounds of formula (I) wherein U.sub.2 is a lathe. oxygen are initially obtained in variants a) - <; ) "B .. ~ A herbicidal or plant growth regulating composition plants < juo comprises an active amount of : > b) at least one compound of the formula (D) or of one of its salts, according to one of the claims 1 to the commonly used ancillary agents in the protection of, or-an ace 7. A method for combating Damaging seeds or for regulating the growth of plants, characterized in that it comprises the application of an active quantity of at least one compound of the formula (I) or one of its salts, in accordance with one of the claims 1 a 4 to the harmful plants or to plants, seeds of the same plants or the surface on which the plants grow The use of a compound of the formula (I) or a salt thereof of com ornu With one of the i eivi ndi falls ions the < as a herbicide or regulator * «Je! growth« je plants 9.- A compound of the formula (ID, (IV), or (VI) as < • e defined in the claimed n 5"15 10 ..- A compound of the formula (VDD * (R Z = NHR (V i l 20 Z = NH. (I X) Z = NO (X) where Z * is NHR3, Y \ 2 or NO2 and R, n, Rl. R2, R3, and Ul on - * r. as defined in the formula (D in conjunction with La rei indication 1