PL142685B1 - Herbicide - Google Patents

Description

The subject of the invention is a herbicide for controlling the growth of undesirable vegetation and regulating plant growth, containing an active ingredient and at least one of such a surfactant and a solid or liquid diluent containing new benzofuran and benzothio as active ingredients. - phenosulfonamides and their agriculturally acceptable salts. Dutch Patent No. 121788 describes the preparation of the compounds of formula 26 and their action as general or selective herbicides. Compounds of formula 2 and 6 R 1 and R 2 can be independently from each other denote an alkyl group with 1-4 carbon atoms, and R3 and R4 may, independently of each other, denote a hydrogen atom, chlorine atom or an alkyl group with 1 to 4 carbon atoms. US Patent No. 3,637,366 describes the compounds Formula 27, wherein R 1 is hydrogen or a lower saturated aliphatic acyl group and R 2 is hydrogen. gnupe 2-pkymidinium, pyridyl, amidine, acetyl or carbamyl. The disclosed zwdaalkd serves to combat bloodstones, peppercorns, endives, clover and Poa annua. French Patent No. 1,468,747 describes para-substituted phenylsulfonamides wherein R is hydrogen, halogen, CF 3 or 10 alkyl. These compounds are used as anti-diabetic agents. In a publication by Logemann et al., Chem. Alb., 53,180,152g (1959) describes a series of sulfonamides, including uracil derivatives and compounds of formula 29 in which R is butyl, phenyl or the group of formula 30, in which Ri is hydrogen or Studies on hypoglycemic activity in rats (oral doses of 25 mg / 100 g) showed that the compounds in which R represents the butyl or phenyl group showed the strongest effect. Other compounds showed weak activity or were inactive. In the publication presented by Wojciechowski, J. Acta, Polon. Pharm. 19, pp. Ai ^ 5 (1962) (Ghem, Ab., 59, 1633e) describes the synthesis of N - [/ z, 6, dimethoxypkyimindinyl-amlide of formula 31. US 4,137,405 describes compounds useful for controlling weeds in wheat of formula 32 wherein R is the group of formula 33 or b 34, R 1 is the group of formula 35, 36, 37 or 36, R3 and R6 are independently of each other hydrogen. , fluorine, chlorine, bromine, iodine, alkyl group with 1-4 carbon atoms, gnupe alkoxy group with 1-4 carbon atoms, nitro group, trifluoromethyl group, cyano group, CH ^ S / O / n-luib GH ^ CHaS (O / n-, R 4 is hydrogen, fluorine, chlorine, bromine or gnupe 142 685 142 685 3 methyl, Re is hydrogen, fluorine, chlorine, bromine or methyl or methoxy group, Rj is hydrogen, fluorine, chlorine, bromine, alkyl group with 1-2 carbon atom, or alkoxy group with 1-2 carbon atoms, R8 is hydrogen atom, methyl group, chlorine or bromine atom, R9 and Rio independently denote aja 'hydrogen atom, methyl group, chlorine atom, bromine atom, W and Q independently from each other represent oxygen or sulfur atom, n is the number 0, 1 or 2, 10 X is hydrogen, chlorine * bromine, methyl group, ethyl group, an alkoxy group of 1-3 carbon atoms, a trifluoromethyl group, a CH 3 S or GH — OCH 2 group, and Z represents a methyl or methoxy group, or their agriculturally acceptable salts, with the illustration that: (a) when Rs is a non-hydrogen substituent, then at least one of the Ra, R4, R6 and R7 groups is a non-hydrogen substituent, and at least two of the R3, R4, Re and R7 groups must be hydrogen, (b) when R5 is hydrogen and R &lt; 4 &gt;, Re and R7 are all non-hydrogen, then all of the Ra, R4, Re and R7 groups must be alibo chloro or methyl, and (c) when Ra and R7 both represent a hydrogen atom, then at least one of the groups R4, R5 or Re must be hydrogen. EP-A-3: 5,893 discloses alkylsulfonylbenzene &lt; RTI ID = 0.0 &gt; ulphonylureas which are used as herbicides. US Patent No. 4,391,627 describes herbicidal benzo [b; Hthiopheno- and benzofuranesulfonylureas in which the suiphonoid group is linked to a heterocyclic ring. Benzodioxole and benzradioxane sulfonylureas having herbicidal activity are described in United States Patent 4,502,882, while benzofuranesulfonylureas exhibiting herbicidal activity are described in United States Patent No. 4,514,211, while benzofuranesulfones and benzofuranesulfones having herbicidal activity are described. in which the thiosufylureido group is bonded to the benzene ring. 45 The presence of undesirable vegetation causes significant damage to the harvest of arable crops, especially those agricultural products that meet basic human needs in terms of food and fiber, such as cotton, rice, corn, soybean, etc. The demographic explosion of recent times and the resulting insufficient supply of food and fiber in the world require increasing the yield of these crops. One way to increase this productivity is to prevent or minimize the loss of a portion of these valuable crops by destroying or inhibiting the growth of undesirable vegetation. A wide variety of materials are available, effective in destroying or inhibiting (combating) the growth of undesirable vegetation; such substances are commonly referred to as herbicides. Nevertheless, there is still a need for herbicides that are still more effective. The invention relates to a herbicide containing new compounds of formula I as active ingredients, showing general or selective activity. pre-emergence or post-emergence as herbicides or plant growth regulating agents. A herbicide for controlling the growth of undesirable vegetation and regulating plant growth, containing an active ingredient and at least one substance, such as a surfactant and a solid or liquid diluent, is characterized by a compound having the formula as active ingredient. 1 "where J is a group of formula 39, 40 or 41, and Q is oxygen, sulfur or SO2, Qi is oxygen, sulfur, SO or SO2, R is hydrogen or methyl, Ri is hydrogen, methyl, methoxy, chlorine, bromine, NO2, CO2R5, SOaRe, OSO2R7 or SO2NR3R9, R2 is hydrogen or an alkyl group of 1-3 carbon atoms, R3 is hydrogen or a methyl group, R4 is a hydrogen atom or a methyl group, R4 is a hydrogen atom, a chlorine atom, a methyl group, a trifluoromethyl group, a methoxy group or a bromine atom. R5 is an alkyl group with 1 to 3 carbon atoms, CH2CH = CHa , CHaCHaOCHa or OH12H2Cl, R "Represents an alkyl group of 1-3 carbon atoms, R7 is an alkyl group of 1-3 carbon atoms or a trifluoromethyl group, Rs and R9, independently of each other. themselves represent an alkyl group of 1-2 carbon atoms, R10 represents a hydrogen, chlorine, bromine atom or an alkyl group of 1-3 carbon atoms, Rn represents a hydrogen atom, a methyl group, chlorine or bromine atom. W is sulfur oxygen atom, A is group of formula 42, 43, 44, 45 or 46, G is oxygen atom or GHH group, X is hydrogen atom, methyl group, methoxy group or chlorine atom, Xi is methyl group, methoxy or ethoxy group, X2 is methyl, ethyl or GHaCF ^ Y is methyl, methoxy, ethoxy, CH2OGH3, NHa, NHCHa, N / CH3 / 2, OH ^ OCHak, formula 47, ethyl, trifluoromethyl, CH2 = OHCHbO, SCHa, HC = CCH2O or CFaCHaO, Y2 is ethyl, methyl, methoxyl, ethoxy, SCH3 or SC2H5 and Z is CH, nitrogen, CCH *, CC2H5, OCl or CBr, and the agriculturally acceptable salts thereof, with the restriction that (1) in the formulas 30 and 40, when Qi is oxygen and Ri is a substituent other than hydrogen, chlorine, bromine or NOa, then at least one of the groups R2 and R3 is an alkyl group, and when Qi is a sulfur atom, then Ri cannot be a NO2 group, (2) in the group Ie of formula 41, when Ri is NO2 or SOaNRsRi, then Rio is dnupe alkyl with 1-3 carbon atoms and Ru is methyl, (3) when X is chlorine, then Ri cannot be rtO 2, (2) in the methoxy group, NH * N1BCH3 or N / CH ^ 2, (4) when Qi is the SO group, then W is oxygen, and (5) when R1 is a substituent other than hydrogen, then Ri represents a hydrogen atom.5 The most advantageous in terms of herbicidal activity or ease of synthesis of lures for both reasons are the following groups of compounds, listed in order of increasing preferred properties: (I) Compounds of general formula I, in which J is Formula 39 and R4 is hydrogen. and (2) The compounds listed under 1 in which W is oxygen and R is hydrogen. (3) Compounds listed in item 2, wherein Ri is hydrogen, chloro, methyl, methoxy, COaRs or SO2R6. (4) The compounds mentioned in item 3, in which R'4 and Ri represent a hydrogen atom, and R2 and R3 independently of each other represent a hydrogen atom or a methyl group. &Lt; 5) Compounds listed in item 4 in which A is a group of formula 42, Z is a group of formula CH or nitrogen and X is methyl, methoxy or chlorine. &Lt; 6) Compounds listed under 5 in which Y is methyl, methoxy, CH2OCH3 or WCHa / * (7) Compounds of general formula I in which J is a group of formula 40. <8) Compounds mentioned under 7, in which W is oxygen and R is hydrogen. (0) Compounds listed in item 8, wherein Ri is hydrogen, chloro, methoxy, methoxy, CO2R5 or SO2R6. (10) Compounds mentioned in item 9, in which Ri is hydrogen and R2 and R3 independently of each other represent a hydrogen atom or a methyl group. (II) Compounds listed in item 10, in which A is a group o In formula 42, Z is CH or nitrite and X is methyl, methoxy or chlorine. (12) The compounds mentioned in item 11, in which Y is methyl, methoxy, OH2OCH3 or N / CH3 / 2. (13) Compounds of the general formula I, in which J is the group of formula 41. (14) Compounds of the formula (13), in which W is oxygen and R is hydrogen. and (I 5) The compounds mentioned in item 14, wherein Rn is hydrogen, Ri is hydrogen, chlorine, methyl, methoxy, CP2R5 or SO2R, and the graipa SO4NHC / W / NRA is bound by is at position 7. (16) Compounds mentioned in item 15, wherein R 1 is hydrogen and R 0 is hydrogen or methyl. (17) The compounds mentioned under 16, in which A is a group of formula 42, Z is a group of formula CH or a nitrogen atom, and X is a methyl, methoxy or chlorine group. (18) The compounds mentioned in item 17, in which Y is methyl, methoxy, CH * OCH3 or N (CH3 / 2). The following compounds are most advantageous due to their exceptionally high herbicidal activity, activity of a plant growth regulating agent, or ease of synthesis, or all of these, the following compounds: 1.1- (N - dioxide 4.6% iMethylpyrimidinium-2 / - aminocar (bonyl] H 2, 3-idi, hy; dro-aiie (tyl-7-n-benzothiophenesiphonamide; 1,11-Nt dioxide (4-ethoxy-6H-methylpyrimphidinyl-10-aminocarbonyl) -2.3 ^ ihy! dro-2H-methyl-7- (benzothiophenesulfonamide; 1,1-dioxide N - {(4,6H-dimethoxypyrimidinyl-2H-ammocaribonydo], 3H-dihydro-2- [methyl-7- (benzolthiophene-ulphonamidine) ; 15 [mu] l, [mu] l &lt; D &gt; N [(4,6'-dimethyl-1,3,5H-thriiazinyl-2) -amdnocar ^ 13on3do] -2 [alpha] 3-idihydro ^ H -methyl-7Hbenisothio [phenonifonamide; 1,1-dioxide Nn [/ 4-methoxy-6Hme) yl-1,3-5-tri-az-3-yl-2-amino-carto 20-benzoithiophenesulfonamide; 1,1-dioxide N4 / 4,6- (dimethoxy-1,1,3,5-triazinyl) N-aminocarbonyl] Haj3H-dihydro-2H-methyl-7H-benzo-thiophenesulfonamide; 2. ^ 3'-diinidroHNH [(4-methoxy-6-methylpyrimaidin] -25 [beta] -amimocarbon ylol-6-methylbenzifuran-THSulfonamide; N4 (4,6-dimethoxypyridinylH21) aninocarbonyl] -2,3-difoydro-2-imethylobenzofuran-7n-sulfonamide; 1,1-N-2-Dioxide N-dimethoxypyrimidinyl [alpha] -30-amino-carphoonyl] n2,3-dihydrolbene-phonamide; and 2,3-dihydro-* N -, [i /, 4-methoxyH6-methylpyrimadinyl-2-ajminocarbonyl} benzo [b] thiophen-35-7-sulfonamide 1,1-dioxide. The active substances of formula I are prepared by as shown in Scheme 1. As shown in Scheme 1, compounds of Formula 1 (wherein W is oxygen) are prepared by reacting a sulfonylcarbamate of Formula 2 with the appropriate amine of Formula 3, wherein Y, R and A are as defined above. These reactions are carried out at 50-100 ° C. in a solvent such as dioxane for a period of 0.5 to 24 hours, as disclosed in European Patent Specification No. 44 & 07. The carbamates of the formula II which can be prepared for this purpose are prepared by reacting the corresponding sulfonamides of the formula IV with the diphenylcarbonate in the presence of a strong base. The sulfonamides of the formula IV present in scheme 1 are intermediates in the preparation of the compounds of the formula 1. Synthesis of the necessary intermediates These sulfonamides are shown in Schemes 2 and 3. As shown in Scheme 2, sulfonamides of Formula 4 can be prepared from the corresponding sulfonylchlorides of Formula 5. The preparation of sulfonamides from ammonium hydroxide and sulfochlorides is extensively described in ° C. literature, -rip. Crossley et al., J, Am, Ohern. Soc., 60, 2223 (1938) and Paller, Monatsn., 92, 677 (1961). There is also a known method of preparation which uses the reaction of sulfochlorides with an excess of anhydrous ammonia at 0 ° C in ethylin ether or Chloirofouftane. 142 685 and uvchlodri of formula 5 can be prepared from the corresponding aimines of formula 6 by diazotization with sodium nitrite in HJC1, and then the diazonium s6L is reacted with sulfur dioxide and mezinium chloride in acetic acid, as reported by Yale and Sowinski. , J. Org. Boor. 25, 1824 (lft & o). Alternatively, the sulfchlorides of formula 5 can be prepared using modifications of the above process, in which the diazotization reactions are carried out in dilute sulfuric acid (20-SO4 / o) at 0-10 ° C for a period of 0 2 to 1 hour. The resulting diazonium s61 is reacted with sulfur dioxide, HCl and mercurial chloride in a solvent mixture consisting of acetic acid and water at a ratio of 1: 1, and an immiscible, inert solvent such as 1, Moroibujt, luib, methylene chloride. at 0-40 ° C for 1 to 24 hours. The method of addition is not critical, but it is often convenient to add the diazonium salt to the slurry containing the sulfur dioxide. The sulfochlorides are isolated by adding water, separating the organic phase, washing the organic phase with a saturated aqueous NaHCO 3 solution and water, and then evaporating the solvent under reduced pressure at a temperature below 50 ° C. The sulfonamides of formula Ia, where J is the group of formula 39, Q is sulfur, and Ri and R'4 are hydrogen, may be prepared from N-III.1- Mbuitylbenzenesulfonamide, as shown in Scheme 3, where R2 is an alkyl group of 1-3 atoms Carbon, R3 and R4 are as defined above, Rj is hydrogen or methyl, R "is hydrogen, methyl or ethyl, and when R" * is methyl then R'2 is hydrogen. shown in Scheme 3 (a) is carried out in situ as follows: the preparation of the dichlithium salt C by reacting N-II tert-1butylbutylbenzenesulfonamphide with two equivalents of n-4-dimethyl lithium at 0- ^ 30 ° C in an inert solvent. like these trahydrofuran, for a period of 1 to 5 hours as described by Lomibardino, 3. Org. Chem., 36, 1843 (1971). Subsequently, N-II tert-ibutylH2-propenylthiobenzenesulfonanide of formula E is prepared by (1) contacting a mixture containing a compound of formula C with elemental sulfur at ambient temperature for a period of 1 to 5 hours, to form lithium thioate of formula E formula D; (B) contacting this mixture with the appropriate allyl halide at 0 ° C. and stirring at ambient temperature for 0.6 to 24 hours to form the compound of Formula 13; and (3) isolating the compound of formula E by adding dilute hydrochloric acid to it, and then separating and concentrating the organic phase. The reaction of organolithium reactants with sulfur to form Mitu thiolates which can be alkylated in situ is known in the art, see for example Oschwend et al., "Organis Reactions", 26, Chapter 1, p. 83 (1079) and cited publications there. 10 15 25 30 35 40 45 55 55 € 5 60 HbuityioA3H6% Hydro-7Hbenzo [b] thiophenesulfonate of formula F by heating the compound of formula E, alone or in an inert solvent such as quinoline or N, N-dimethylamino at ISO-30 ° C for a period of 0.25 to 2 hours to effect cyclization The compound of formula F is isolated by adding an inert solvent such as ether or methylene chloride, thoroughly washing with dilute hydrochloric acid and water, followed by separation and concentration of the organic phase. The compound of formula F can be purified by column chromatography and by recrystallization. Reaction 3 (c) of Hlrz.-ibutyiosuifonamides of formula F is then de-icilated to form sulfonamides of formula 4a, by the reactions of the compounds of compounds of formula F with excess trifluoroacetic acid at 20 ° C to 40 ° C for about 10 to 30 hours. Compounds of formula IVa are isolated and purified by concentrating the reaction mixture, adding methylene chloride to the residue, washing the suspension with dilute aqueous NaHCO 3 solution and concentrating the organic phase. Alternatively, Tert.-tutylsulfonamides of formula F can be converted to sulfonamides of formula IVa by heating in motanol containing at least an equimolar amount of hydrochloric acid and then concentrating the reaction mixture and removing the product with ether. 2 are the starting materials for the preparation of compounds of formula I which can be prepared using the following general methods. A number of starting 4- and 7-amidno-2,3-dihydrobenzofurans of formula 6 are known in Scheme 2, so, for example, 4-amino-2,3-dihydro-2-dimethylbenzofuran can be prepared as described by Cruickshank et al., J. Med. Ohem., 13, 1110 (19719); 7-amlinoH2, 3-d-ylhydro-2, 2-dd-methyllbenzofuran as disclosed in Dutch Patent Specification No. 6,602,601; 7-amino-3-H-dihydro-2-Hrneityi-benzofuran as disclosed in Belgian Patent Specification No. 744,858; 4-amino-2, 3-th-dihydro-benzofuran as set forth in US Patent No. 3,963,7117; and 7-amino-(2, CN-dihydrobenzoifurane) as described in U.S. Patent No. 3903717. 7nmdnoA3- (dihydrobenzofurans of formula 6 in Scheme 2y in which R 1 is hydrogen, methyl, methoxy, chlorine or bromine can be prepared by a method analogous to that described in Dutch Patent Specification No. 6,602,601. This process is illustrated in Scheme 4, where Ri is hydrogen, methyl, methoxy, chlorine or bromine, Ra is an alkyl group of 1-3 atoms, R3, R4 and R% are as defined above, RV is hydrogen or methyl, and R "is hydrogen, methyl or ethyl; when R" 2 is ethyl, then R " '2 represents a hydrogen atom. As shown in Scheme 4, this preparation process involves three steps: (1) the reaction of a 3- or 4- (substituted) t'-2-nitrite (rophenol with a disproportionally substituted adyl chloride with the formation of an intermediate compound for a compound of formula G, (2) heating this compound at an elevated temperature of 150 to 300 ° C with the catalyst to effect cyclization to form the compound of formula H, and (3) reducing this compound to form the compound of formula 6a. The first reaction is carried out in a warm protic solvent such as ethanol in the presence of a weak base such as K 2 CO 3. The cyclization step is usually carried out without solvents at elevated temperatures in the range of 15 ° 0 to 300 ° C. for a period of 1 to 24 hours. A Friedel-Grafts catalyst such as magnesium chloride is usually used to initiate the cyclization reaction and increase the yield of the product. The intermediate compound of formula H can be purified by recrystallization of the hub by chromatography. The reduction step can be carried out by any of the known methods for reducing nitro groups to pimdnum groups. Thus, for example, an intermediate of formula H can be catalytically redoxidated with 5% palladium on activated carbon using ethanol as solvent at a temperature of about 26 to 45 ° C and a pressure of 1013-3 ° C. Alternatively, the compound of formula H may be heated with tin chloride in concentrated hydrochloric acid at about 25 to 80 ° C for a period of 0.5 to 3 hours to form the compound of formula 6a. Alternatively, rearrangement reactions The daisena-cyclization shown in Scheme 46 above can be carried out in stages as follows: (a) the phenyl allyl ether of formula G can be regrouped at about 150 to 200 ° C by heating it for 0.5 to 10 hours alone in the presence of a suitable high-boiling solvent such as diethylaniline to give the corresponding 4- or 5- (substituted) -6-nitro-2-allylphenol as described by SJ Rhoads and NR Raulims , Organic Reactions, Vol. 22, pp. 1-21513, John Wiiey and Sons, N ew York and London, eds. W. G. Daulben; and (it) this compound can be cyclized to a dihydrobenzofuran of formula H using methods extensively described in the literature for analogous types of reactions. Thus, for example, heating the reshaped proctact with pyrimidine hydrochloride (R4 and R5 are not methoxy) or with acidic reagents such as hydrogen bromide in acetic acid, or with a Friedel-Craits catalyst such as magnesium chloride. so-called, can give the compound of formula H as described by Claisen and Tietze, Ann. 449, 8.1 (d926) and 442, 235 (1925); Arnold and Mc Cool, J. Am. Chem. Soc, 64, 1315 (1942); J. Bntel et al., Ibdd., 73, 2365 (; 0.151); P. Cruickshank et al., J. Med. Chem., 13, 1J10 (1970); and Q, Bartz et al., J. Am. Chem. Soc. 57, 37.1 (1935). 7 * Aimino-2,3-dihydroibenzofuranes of the formula 6 occurring in scheme 2 »in which Ri is the group OSO2R7, SOaRe alibo COaRj, can be prepared as shown in scheme 5, in which Rj is an alkyl group of 1-3 carbon atoms, Ra 1 R4 have the meanings given above, and Rj is the group OSOjR7, SOJR7 or COjR * According to the scheme 5, 6, chloro-7-nitroH2,3Hii-hydrobenzofuran of formula 7 is reacted with the reagemtaim discussed below to form of an intermediate compound b of formula I containing the desired group R 1. A niitro compound of formula I is reduced to form a compound of formula 'Gb. These reactions can be carried out by methods known in the art. An intermediate compound of formula I, in which Ri denotes the group OSObCHs, for example, is produced in two steps: (1) heating the compound of formula 7 with one equivalent of a strong base such as hydroxide sodium or potassium in dimethylformaimlide at 50 to 80 ° C for a period of 1 to 8 hours, to form a plate of formula I in which R 1 is a hydroxyl group, and (2) reaction of the resulting phenol with an acid chloride methanesulfonic acid in the presence of a base such as triethylamine in an inert solvent such as tetrahydrofuran at a temperature of 25 to 7 ° C for 1 to 24 hours to form a compound of formula I, wherein R 1 is gnupe OSOaJGHa . An intermediate compound of formula I, in which R x is SO2CTL, for example, is prepared in two steps: (1) heating of the compound of formula VII with one equivalent of sodium methyfloimercaptide in dimethylformamide at 25 to 80 ° C, within and up to 8 hours, to form a compound of formula I, in which Ri is a SCHa group, and (2) oxidation of the obtained compound with 30% hydrogen peroxide in acetic acid solution at 0 ° C to 6tO ° C, in 1 to 8 hours, to form a compound of formula I, wherein R 1 is SOaCHa. The intermediate compound of formula I, in which R 1, for example, is the group CO 1 Cl H a, is prepared in three steps: (ii) reacting the compound of formula 7 with one equivalent of potassium cyanide in diumeitylformimphide at 50 to 80 ° C. for 1 to 24 hours to form a compound of formula I in which R 1 is ON, (2) hydrolysis of the cyano group to camboxylic acid by a number of methods known in the art, for example the compound of formula I in which R 1 is the CN group can be heated under reflux in concentrated hydrochloric acid in acetic acid solution to form a compound of formula I, in which R 1 is COsfH, and (3) to convert the carboxylic acid into acid chloride which is then watered reaction with methanol to form the compound of formula I, in which R 1 is the group CO 2 CH *. The latter reactions can be carried out by methods known in the art. In the final stage of the reactions shown in Scheme 5, the compound of formula I can be reduced wac to The compound of formula 6b and the method described previously in Scheme 4. The starting 6-chloro-7- [beta] -2y3-dihydirobenzo] uranium of formula 7 is also prepared by the methods described above in Scheme 4. Likewise 4-amMo-2 ^ 3 -dlihydroclibenzo4uranes of formula 6 appearing in Scheme 2, in which H10 15 20 25 30 35 40 45 50 55 00 [142 685 and 12 is SO ^ Rg, OSO2R7, alpha CO2R5, R2 is an alkyl group of 1- Carbon dioxide, and R3 and R4 are as defined above, can be prepared by the methods described in Scheme 5. Thus, starting from the appropriate 5-chloro-4-nitro-2,3-dihydrolbenzofuran and carrying out the reactions described above in Scheme 5 , one skilled in the art can obtain the aforementioned 4-Hamino-2,3-idihydrobenzofurans of the formula 6. The starting 5-chloro-4-nitro-2,3-dihydrobenzofurans are described below in Scheme 7. 7-Aniino-2,3-dihydroibenzofurans in formula 6, in which R1 is NO2 or SOgNRsRg, can be prepared as shown in scheme 6. wherein R2, R3 and R4 are as defined above and Ri is NO2 or SOzNRaRg. According to Scheme 6, 7-acetimido-2,3-dihydrobenzofuran of formula 8 is reacted with the reactants described below to form the intermediate 0. Formula J, which is then deacetylated to form the compound of formula 6C. An intermediate compound of formula J, wherein R 1 is NO 2, is prepared in two steps: (1) nitration of the compound of formula 8 with a solution of nitric acid in acetic acid, at about 10 to 25 ° C for 0.5 to 5 hours to form a mixture containing a portion of the compound of formula J in which R 1 is NO 2; and (2) separating the compound of formula J from the mixture by recrystallization or chromatographic separation. An intermediate compound of formula J, in which Ri denotes the group SO2NRg, is prepared in three steps: (1) chlorosulfonation of the compound of formula VIII with chlorosiphonic acid to form a mixture of products containing, inter alia, the compound of Formula J, wherein R 1 is SO 5 O, (2) reacting the resulting mixture with a suitable dialkylamine in an inert solvent such as tetrahydrofuran at a temperature of about 10 to 60 ° G for 0.5 to 10 hours, with the formation of m Among others, the compound of formula J * - I in which R 1 is a group of the formula SO SONRaRo, and (3) isolation of the desired intermediate compound of formula J by recrystallization or chromatographic separation. The chlorosulfonation step can be carried out by reacting the compound of Formula 8 with an excess of chlorosulfonic acid, that is, about an excess of three equivalents, at a temperature of about 25 to 7 (PC, in an inert solvent such as chloroform, within 0 hours). 5 to 8 hours. Deacetylation of a compound of formula J to form a compound of formula 6c can be accomplished by saponification or hydrolysis of Tcacid. Thus, by heating the compound of formula J at reflux temperature in 90% ethanol with one equivalent of sodium hydroxide for 0.25 to 3 hours, a compound of formula VI can be obtained. Alternatively, heating of a compound of formula J at 50 to 80 ° C with hydrochloric acid in acetic acid for 0 5 to 3 hours can also give the compound 10 of formula 6. The starting compound of formula 8 can be prepared by known methods, that is, by heating at 50 to 10 ° C the corresponding 7-amino-2tf3-dihydrofoenzofuran in benzene acetic water, from cat alitically acting amounts of sulfuric acid in 1 to 10 hours. Similarly, 4-amino-2,3-dinidrofoenzofurans of formula 6 in Scheme 2, in which R 1 is the group NO 2 or SOefNRaRa, can be prepared by the methods described in in Scheme 6. Thus, starting from the appropriate 4-acetamido-2,3L-H-dihydrobenzofurane and carrying out the detachable reactions described above in Scheme 6, 4-amino-2,3-dihydro-nitrophomzofurane can be obtained and 4 - [alpha]: mino-5- (N, N, diallkylsulifonamido) -2.3- dihydrobenzofurans of the formula VI in which the substituents R2 to R4 'have the meanings given above. The starting 4-acetamido-2,3-dihydroibenzofurans can be prepared from 4-amphino-2, S-dinidrofoenzofurans by methods also described in Scheme 6. 4-Namino OH2,3-idilhydrofoenzofurans of formula 6 as described in Scheme 2 wherein Ri is hydrogen, methoxy, chlorine, bromine, CO2R5 or OSO2R7 can be prepared as shown in Scheme 7, where R2 is an alkyl group with 1-3 carbon atoms, R3 and R4 are as defined above, and Ri represents a hydrogen atom, a methoxy group, a chlorine atom, a bromine atom, a CO2R5 group or an OSO2R7 group. According to Scheme 7, 5-amino-2,3-dihydro-4-nitrobenzofuran of formula 9 is diazotized and then reacted with the appropriate reactants to form an intermediate compound of formula K, reduction of which gives the compound of formula 35 6d. The diazonium salt can be prepared using sodium nitrite in dilute siracic acid (20 to 50 ° C) at about 0 to 10 ° C by methods known in the art, see, for example, Arnold and McCboi, J. Am. Chem. Soc, 40 64, 1315 (1942;). An intermediate compound of formula K, wherein R 1 is as defined above, can be prepared from the diazonium salt by methods known in the art. 'Thus, an intermediate compound of the Formula K wherein Ri is chlorine or bromine can be prepared by heating the diazonium salt with cuprous chloride and hydrochloric acid, alfoo with cuprous bromide and hydrobromic acid, using Sandmayer reactions as for 50, see Powers, J. Med. Chem., 19, 57 (1976). An intermediate compound of formula K in which Ri is methoxy can be prepared in two steps: (ii) an intermediate compound of formula K, in which Ri is hydroxy, is prepared by heating under a diazonium reflux condenser. sold from mdeidisulfate (Sr0 / ©) solutions, which is a technique known in the art for producing phenols from diazonium salts, see, for example, Arnold and McCool, J. Am, Chem. Soc., 64, 13 ( 15 (1942), and (2) the phenol obtained can then be methylated by a number of known methods to obtain a compound of the K-weight, in which Ri is a methoxy group. For example, heating the phenol with methyl sulfate in 85 temperature of 25 ° to 60 ° C in water in the presence of an equivalent amount of NaOH gives a compound of formula K, where Ri is methoxy group. An intermediate compound of formula K, where Ri is OSO * R7 can be prepared in particular The reaction of the phenol described above with the appropriate sulfchloride and base is therein a as triethylamine in an inert solvent such as tetrahydrofuran at a temperature of about 0 to 60 ° C. An intermediate compound of formula K where Ri is the group CO2R5 is prepared as follows: (1) an intermediate compound of formula K in in which R 1 is ON, is prepared by the Sandmayer reaction, ie by heating the diazonium salt with cupric cyanide by methods known in the art as described by Hansch and Schmildlhalter, J. Org.Ohem. 20, 1056 (1056); (2) an intermediate compound of the formula K, in which R 1 is COaH, is prepared by heating the resulting cyanosides for 1 to 10 hours under reflux with hydrochloric acid in acetic acid; and then (3) an intermediate compound of formula K, in which R 1 denotes the group COiRg, is prepared by converting the carboxylic acid into an acid chloride which is then reacted with the appropriate alcohols to form the compound of formula K; wherein Ri is CO2R5. Reactions (3) are carried out according to methods known in the art. An intermediate compound of formula K, wherein R 1 is hydrogen, is prepared by reacting a diazonium salt with 50% hypophosphoric acid at 0 to 20 ° C, for 1 to 24 hours as described by Bordweil and Stange, J. Am. Chem. Soc., 77, 5039 (19515). The final step in Scheme 7, i.e. the reduction of the compound of Formula K to form the compound of Formula 6d, is carried out by the methods described above for Scheme 5. The starting compounds of Formula 9 in Scheme 7 can be prepared as described by Arnold. and McCool, J. Am. the bottom. Soc., 64, 1315 (1942), Arnold and McCool describe the preparation of 5-amino-2,3-dihyico-2H-methyl-4H-nitroibenzofuran in a multistage process starting from the reaction of 4-hydroxyacetophenone with allii bromide. By reacting 4H-hydroxyacetolenone with other appropriately substituted alliii bromides or alliii chlorides, and using the reaction sequence and conditions described in this publication, one skilled in the art can prepare the compounds of formula 9 of Scheme 7. 6 of Scheme 2, in which R 1 is methyl, hydrogen, chlorine or bromine, may be prepared by a method analogous to that described by Cruickshamek, J. Med. Ohem., 13, 1110 (1970). This process is described in Scheme 8, wherein R2 is a 1-3 vegA, R3 and R4 alkyl group. the meanings given above, R1 is hydrogen, methyl, chlorine or bromine, and R3 is hydrogen or methyl, and R'2 is hydrogen, methyl or ethyl; when R "a, 685 14 is ethyl, then R 2 is hydrogen. In the process of Scheme 8, preparation is carried out in three steps: (1) the reaction of the 2- (substituted) -5-5- hydroxybenzacetamide of formula 10 with the appropriately substituted chloride. allium and potassium carbonate at a temperature of about 25 to 80 ° C in an inert solvent such as acetone, to form an intermediate compound of formula L; (2) heating this compound at elevated temperatures, about 150 to 30 ° C, with a suitable FriedeKfrafts catalyst. such as magnesium chloride to effect cyclization with the formation of 5- (substituted) -4-acetamido-α3H-dihydrobenzofuran; and (3) deacetylation of this compound in the usual way leads to the formation of the compound of formula 6e. Using the methods described above in Schemes 4 and 6, so starting with the appropriate 2-20% polyolyl J-hydroxy-benzacetamide formula 10 and using the reactions and conditions described in steps (a) and (b) are Chemistry 4 and step (b) of Scheme 6, compounds of formula 6e can be obtained. The 4- and 7-amdnobenzofurans of formula 6 used in Scheme 2, in which Ri is hydrogen and R10 and Rn are hydrogen or methyl, can be prepared by known methods. Such methods have been described, for example, by Pene et al., Buli. Soc. Cihim. France, 586 (1966); Rodighiero et al., Gazz. Chim. ItaL, 91, 90 (1961); Royer et al., Bull. Soc. Chim. France, 1026 (1970); Kawase, Chem. Indium. (London) * 687 (197i0); Belgian Patent Specification No. 744 859; Kawase et al., Bull. Ohem.Soc. Japan, 44, 749 (1971); French Patent Specification No. 2,338 € 411; U.S. Patent Nos. 3, 577,441 and 3,452,033. 7-Aminobenzofurans of Formula 6 appearing in Scheme 2, where R 1 is hydrogen, methyl, methoxy, chlorine, bromine 40, CO Rs, SOjR, or OSO, R7 can be prepared as shown in Scheme 9, wherein R2, R3, and R4 have the meanings given above, with the proviso that at least one of R * or R $ must be a hydrogen atom, R 1 is a hydrogen atom, a methoxy group, a chlorine atom, a bromine atom, a R 5 group, SO 4 R 6 or OSO 4 R t, R n is a hydrogen atom or a methyl group, and R 0 is a hydrogen atom or an alkyl group with 1 to 3 carbon atoms.50 As shown in Scheme 9, 7-Amphilofurans of Formula 6f can be prepared from the corresponding 7N-nitro, 3H-dihydrotoenzafuranes of Formula 11 in which at least one of R, or Rs is This process involves dehydrogenation reactions followed by reduction reactions Revival can be performed using the method described by Geisman, J. Am. Chem. Soc., 72, 3226 (1950) and Hurd. J. Aim. Chem. Soc., 80, 47111 (1968). Thus, the compound of formula 11 is subjected to a dehydration reaction in two steps: (1) 8-dihydrogen benzene, ffuran of formula L1 is heated at 60 to 80 ° C for 1 to 24 hours, with N-bromodmide succinic acid and benzoyl peroxide to serve as a catalyst in otolojejt-1421 organic solvent such as benzene, benzene or carbon tetrachloride, thereby causing bromination of the non-aromatic part of the time. briefcases with creation! an intermediate compound of the formula M; (2) this intermediate is heated with excess N, N-dimethylaniline, alone or in an inert aproiton solvent such as toluene, for 1 to 24 hours, causing cleavage of hydrogen bromide to form 7-nitrobenzofuran of formula N. The reductions of this compound to form the 7-niinobenzourane of Formula 61 can be carried out by any of a number of methods known in the art for reducing niitrobenzofurans. Thus, for example, according to the method disclosed in Belgian Patent Specification No. 744,858, catalytic reduction of a compound of formula N nifcieim Raney in an inert solvent such as ethanol at a temperature of about 25 to 7 ° C and a pressure of 1013-3039. The hPa of hydrogen gives the compound of Formula 6f. 20 Many of the starting compounds of formula 11 are described above in Schemes 4 15. Likewise, the 4 aminobenzoruranes of Formula 6 in Scheme 2, wherein R 1 is hydrogen, methoxy, chlorine, bromine, COsRa. , OSO, Rt1- and BSOaRe, and R10 being a hydrogen atom or an alkyl group of 1-3 carbon atoms, and Rn being a hydrogen atom or a methyl group, may be prepared by the methods described in Scheme 9. Thus, starting from the (Relevant compounds, such as 5- [substituted] - 2'-dihydro-4-nitrobenzofuran and carrying out the reactions as described in Scheme 9, can prepare the proper 4-aminobenzofurans of formula 6. Preparation of many of the starting 5 The - (substituted) -2.3 dihydro-5-hydroxy nitro-benzotfuranes are described above in Schemes 5 and 7. The 7-aminobenzofurans of Formula 6 occurring in Scheme 2, in which R 1 solubilizes hydrogen, methyl, chlorine , bromine, methoxy, or SO4R8 can be prepared as shown in scheme 10, where Ri is a hydrogen atom, a methyl group, a chlorine atom, a bromine atom, a methoxy group or a SOaR * group, R1 is a hydrogen atom or a 1-3% carbon alkyl group, and Rn is a methyl group. the preparation of these compounds requires three steps: (1) reacting 3-7 | substituted (-2-nitrophenol) with an al &lt; cMoroketone such as chloro-propanone for 1 to 8 hours at 30 to 80 ° C in the presence of a base such as K ^C0ai in an inert solvent such as acetone to form an intermediate compound O; (2 cycles of this compound with the formation of 7-nitrobenzo-uranium; and (3) reduction of this compound with the formation of 7-aminobenzurate p-formula 6g. 0.5 to 24 'hours. Other methods of making benzoruranes from the phenoxypro * of PaniAow are also known, see for example Pene, Bull. 687 (19 ^ 9); and Kawase et al., Ruffil. Chem. Soc. I (Pan, 44, 749 (1971). The reduction step can be carried out as described in Scheme 9. (A) oxidation of the intermediate 7-nitrobenzofuran in which Ri is SR1 with 3 * 0% peracetic acid in acetic acid at 0 ° C, in which R 1 is SO 4 Re is prepared by (a) to G0 ° IC, with the formation of the intermediate 7-nitro) benzotfurane, in which R 1 is the group SOaR i, and (ib) reductions of this compound to form the compound of formula 6g, in which R 1 is the group SOaRfc using the methods described in Scheme 9 above. The 7-aminobenzo! Furans of formula 6 in Scheme 2, where Ri is NO2 or SO2NR8R9, and Rio is an alkyl group of 1-3 carbon atoms and Rn is a methyl gonupe, can be prepared as shown in Scheme Id . The reactions shown in Scheme 11 can be carried out as previously described with respect to Scheme 6. Thus, by nitration or chlorosulfonation of the appropriate 7-acetami-dobenzofuran of formula 13 using the methods described in scheme 6, the desired compounds of formula 6h can be prepared. 4Haminobenzofurans of formula 6 in Scheme 2, where Ri is SOaNRsRg, Rio is an alkyl group of 1-3 carbon atoms and Rn is methyl, can be prepared using the methods described in Scheme 11. Thus, starting with the appropriate 4-acetimidobenzofuran and reacting it as described in Scheme 11, the desired 4-aminobenzofurans of formula 6 can be prepared. 4-amino-benzofurans of formula 6, occurring in Scheme 2, in which R 1 is methyl, chlorine, bromine or Hydrogen can be prepared analogously as described by Kawase et al., Bull. Ohem. Soc. Jap, 749,44 (1971). This process is illustrated in Scheme 12, wherein R 1 is hydrogen, chlorine or bromine, or a methyl group, R n is methyl and R 0 is hydrogen or an alkyl group of 1 to 3 carbon atoms. involves three steps: (1) refluxing an appropriately substituted 4-substituted β-nitroiphenol with an alphanchloroketone such as chloropropanone for 1 to 8 hours in the presence of a base, for example K2CO3, in a solvent such as an example of acetone to form the intermediate compound P: (2) cyclize this compound to form 4-nitrobenzofurane; and (3) reducing this compound to form 4-aminobenzofurarium VI. The cyclization step may be carried out in polyphosphonic acid at a temperature of about 80 to 120 ° C for 0.5 to 24 hours. The reduction step can be performed as described in; diagram # above. The 4- and 7-amino-phyl, 3-hydro-benzo (b] thiophenes of formula 6 in Scheme 2, where R'4 and Ri are hydrogen, can be prepared using the Rucherer reaction as shown in in Scheme 13, where Rj, R3 and R4 are as defined above Reactions of Scheme 13; may be carried out using literature conditions for the Bucherer reaction, see for example Boswell et al., J. Heterocyciic17 142 685 l * Cliem ., 5, 69 (1968). A suitable 4- or 7-hydroxy n2iO * ydroxy [b] tdofen of Formula 15 is heated with concentrated ammonium hydroxide, sulfur dioxide and water in an autoclave at a temperature of about 140 to 180 ° C., for about 10 to 30 hours, to obtain the compound of formula VI. The starting compounds of formula 15. can be prepared by conventional methods. The methods are also disclosed, for example, in German Patent Specification 2 252 335; Art. balls, as published by Kilsheiimer, J. Agr. Food Chem., 17, 91 (1969); and in German Patent Specification No. 2,534,857. 7-amino-3-dihydroi benzo [ib] thiophenes of formula 6 in Scheme 2, where R 1 is hydrogen, methyl, methoxy, chlorine or bonoim, can be prepared as shown in Scheme 14, where R 2 is an alkyl group of 1- 3 carbon atoms, Ra, R4 and R'4 are as defined above, Ri is hydrogen, methyl, methoxy, chlorine or bromine and R '* is hydrogen or methyl; R "* represents a hydrogen atom, a methyl group, an ethyl hub; when R2 is an ethyl group, then R'2 represents a hydrogen atom. According to scheme 14, the process requires two steps: in step 14 (a) 3-or 4-t) | the substituted (-2-aminotrophenol) is reacted with the appropriately substituted allyl chloride or allyl bromide to form the intermediate compound Q. The reaction is carried out in a warm protic solvent such as ethanol in the presence of an equal amount of base such as sodium hydroxide for 1 to 10 hours. After dilution with water, product Q is isolated by extraction with methylene chloride and concentration of the organic phase. The compound Q can then be purified by chromatography. Naltomdast in step 14 (b) the product Q is heated to a temperature of 200 to 300 ° C for about 0.5 to 5 hours to cause cyclization to the compound of formula 6k. In addition to having a 5-membered condensed breast product of formula 6k there is a 6-membered ring isomer of this compound. The original product of Formula 6k can be separated and purified by fractionated distillation orbb with the aid of chromatography. The 7-aminoH2.3Hddlhydrolbenzo {ib] thiophenes of formula 6 occurring in Scheme 2, in which R 1 represents a hydrogen atom, a methyl group, a methoxy group, a chlorine atom, or a bromine atom, can be prepared by a method analogous to that disclosed in the United States Patent Specification No. 4,032,649, a portion of which is provided herein by way of illustration. The relevant part of the description is illustrated in Scheme 15, wherein R 1 is an alkyl group of 1-6 carbon atoms, Ra and R are as defined above, R 4 is a hydrogen atom and Ri represents a hydrogen atom, a methyl group; methoxy, chlorine or bromine. U.S. Patent No. 4,032,649 discloses the preparation of 7- amino-2-H-dihydro-12-dto by a six-step reaction sequence starting from the corresponding 5-or 6-v. By going through the six reactions described in US Patent No. 4 03 & 649, 5- or 6- (substituted) -7-amino-2,3H-dihydrobenzo, [ib] can be prepared from -7-n4trto-2? 3Hddh3? ) thiophenes of formula 01. The starting compound of formula 16 can be prepared by the methods described in Scheme 4. The step-by-step sequence of reactions in Scheme 15 includes: (a) Reactions of the compound of formula 16 with 10 IIIH-potassium butoxide in dimethyl sulfolide at 0 ° to 60 ° C. C, at 0.6 to 18 hours, to form 6-nitro-4 or 5-substituted [beta] -substituted (2-vinyiphenol). (b) reacting this compound with sodium hydride and dimethylthiocarbamyl chloride in tetrahydrofuran at 0 to 0 ° C for 1 to 10 hours to form O [6-nitro-4-luib 5V-substituted H-pyrivinyl] Of -N, N-dimethylcaribamate, (c) heating this compound in a nitrogen atmosphere at a temperature of 1450 to 2020 ° C for 0.5 to 5 hours to form S-P6-niifcro-4ulb 5V-substituted n -phi-vinyl] HN, NH-dimethyl carbamate, (d) reduction of this compound with iron powder in acetic acid, at 25 to 90 ° C for 0.6 to 3 hours, to form S- [6- Aimino-4 or 5-subs (ta-wione-gOt) -i2-vinyio] ^^^ imethylcarbamdate, (e) reactions of this compound with potassium hydroxide in a water-methanol mixture at 40 to SO ° C for 1 to 24 hours, to form 6-amino-4- or 5- (substituted) -2-vinylthiophenol, and (f) cyclizing the compound by heating under nitrogen at 150 to 250 ° C, within 0.15 - up to 6 hours, zu (construct The zero of the compound of "formula 61, present in scheme 35 15. 7-amino-i2,3HdBnydrolbenzolb] thiophenes of formula 6 present in scheme 2, in which R 1 is the group COrfts, OSOaR7 or SOjR" can be prepared as shown in scheme 16 wherein R 2 is an alkyl group of 1-3 carbon atoms, Ra is as defined above, R 4 is hydrogen, and R 1 is CO 1 R 5, OSO 4 R 7 or SO * R ". luibbromo (-7-nitro), 3ndi (hydrolbenzo [ib] ltik) * en R is reacted with the reagents described below to form the intermediate compound S containing the desired group R 1. The nitro compound S is successively reduced to form a compound of formula Om. These reactions can be carried out by known methods. Thus, the compound S in which Ri represents the group OSO * R7 or COjR *, methods similar to those described in Scheme 5 above can be prepared for the preparation of compound I, wherein Ri represents the group OSOjRt or CO * R5. . Compound S, wherein R 1 is SO 4 R *, is prepared by reacting R with the appropriate salt of sulfonic acid, ie, KSO 4 Re, in an inert solvent such as dimethyldifimide at a temperature of about 40 to 100 ". 0 ° C for 1 to 8 hours The nitro compound S reduces sde to an amine of formula 6 by iron powder in acetic acid in ethanol solution at about 50 to 80 ° C for 1 to 5 hours. Compound R can be produced by methods similar to those described above in Scheme 142, 685 19 and Mat. 15 and in United States Patent No. 4,032,649. Thus, the corresponding S - N-chloroAufo bromo -2-Vinio] - ^^ dimeftyttothiokaribaimdniai can be reacted with potassium hydroxide to form the corresponding 6H-nitro-5-chlorO | / or bromo (-2-vinylthiophenol). The theine compound can then be heated at elevated temperatures. 150 to 250 ° C. to effect cyclization to form a mixture of sulfates the R compound and the corresponding 7-chloro (bub bromoi) -8-nirt; rithiochromate. The R compound can be isolated and purified by fractionated distillation or by chromatography. , • 7-amanoH2,3idihyidroibenzo [ib] itio (the phenyls of formula 6 occurring in Scheme 2, where Ri denotes methyl, alto hydrogen, chlorine, bromine, methoxy, COaJR5 or OSO2R7, can be prepared as shown in in Scheme 17, where R2 and R'4 are hydrogen, R3 and R4 are as defined above, Ri is hydrogen, methyl, chlorine, bromine, methoxy, GO ^ Rs or OSO ^ R7, Rid is hydrogen atom or an alkyl gap with 1-3 carbon atoms, while Ru represents a hydrogen atom or a methyl group. Stepwise reduction of benzoI to form 2,3-dhydroibenzo [b] thio <- phen is known in the art, see, for example, Bordiwell and Stange, J. Am. Chem. Soc., 77, 59) 39 30 (1955) and Bordwell and McKeilin, ibid., 73, 225 (1 (19i5il). Reactions according to Scheme 17 may be carried out using the methods contained in the cited publications. In the first step, 7-nitrobenzo (b] - thiophene of formula 17 is oxidized with 30% hydrogen peroxide in acetic acid at a temperature of about 50 to 115 ° C for 0.5 to 2 hours to form ethyl benzo (ib} thiotphene dioxide) T. The intermediate compound T is catalytically hydrated 5% of palladium on charcoal under a pressure of 1013-3039 mbar, at a temperature of 25 to 45 ° C, in ethanol, with the formation of 2,3-dihydrobenzo lyl-dioxide [b] thiophene U *. In the final step, compound U is refluxed with zinc and concentrated hydrochloric acid in acetic acid solution for 1 to 3 hours to form a test specimen of formula 6n. There are many of the starting 7KnLtrdbenzo [ib] thiophenes of formula 17. 4 Hamino-2 ^^ hydroibenzo [b], thiols of formula 6 50 occurring in scheme 2, in which, Ri is a and t Hydrogen, methyl, chlorine, bromine, methoxy, CO1R5, OSOzR7, or SOaiRe can also be prepared using the methods described above in Schemes 16 and 17. Thus, starting from the appropriate 5-chloro-4Hnitro Hydrobenzo [b] thioiphene and by carrying out the appropriate reactions described in Scheme 16, it is possible to prepare the desired compounds in which Ri denotes the group SOiRe. Likewise, starting from the appropriate 5% substituted MHn ^ ^ and carrying out the appropriate reactions described in Scheme 17, it is possible to prepare the desired compounds in which Ri is hydrogen, methyl, methoxy, chlorine, bromine, • * pe COR or OSO R. The required starting 5VpodS (low-4-nitrobene (zo [b] thiophenes. 4- and 7-amdnoh2,3Hdahydrobenzo [ib] thiophenes of formula 6 in Scheme 2, in in which Ri is the group SO2NR8R9, can be prepared using the methods previously described in Scheme 6. Starting with the appropriate 4- or 7-acetaminide-α-HdihyldrobenzoIblitaophen and carrying out the chlorosulfonation reactions described in Scheme 6, it is possible to prepare The desired 4- and 7-amino-H 2, 3-dihydrobenzo [b] lthiophenes of the formula 6. Starting acetamides can be prepared by known methods, that is, for example, by refluxing a 4- or 7- amino-amino acid under reflux. l2,, 3-idihydroibenzo [ib] thiophene in acetic anhydride in the presence of kw sulfur as a catalyst. The above amino compounds can be prepared by the Bucherer reaction as described above in Scheme 13. 4- and 7-Amine O) benzo [b] thiophenes of Formula 6 in Scheme 2, where R Ri is hydrogen, R10 is hydrogen or an alkyl group of 1-13 carbon atoms, while Rn is a hydrogen atom or a methyl group, may also be prepared by the Bucherer reaction. Starting from a suitable 4-or 7-aminobenzo [ib] thiophene and carrying out the reactions described in Scheme 13, the desired 4- and 7-aminobenzo [ib] and oenes of formula 6 can be prepared. Of the biliary 4- and 7H-hydroxybenzo [ib] thiophenes. The 4-aminoibenzo (b] thiophenes of the formula 6 of Scheme 2, wherein R 1 is hydrogen, methoxy, chlorine, brom, CO 2 R 5 or OSO 2, may be prepared as shown in Scheme 18, wherein R 1 is hydrogen, methoxy, chlorine, bromine, CO 2 R 8 or OSO 2 R 7, R 10 is hydrogen or b alkyl group with 1-3 carbon atoms and R n is hydrogen or methyl. with Scheme 18 5-amino-4-nitrobenzo [bithiophene of formula 18 is diazotized and then the diazonium salt is reacted with the appropriate reagents to form the intermediate compound V, the reduction of which yields the compound of formula 60. The diazonium salt can be prepared using sodium nitrite in dilute sulfuric acid (ftO to 50%) at 0 to 10 ° C using the well-known aminobenzotb] -thiophene diazotization method as, for example, described by Bordwell and Stange, J. Am. Chem. Soc., 77, 5939 (1955) one compound V, in which Ri has the meaning given above, can be prepared from the diazonium salt using the methods described in Scheme 7. The reduction step to form a compound of formula 60 from an intermediate compound V can be made using any of a number of methods known in the art. methods for reducing nitrobenzo {ib]! thiophene to aminobenzo [ib] thiophene tf as described, for example, by Bordwell and Ailbisetti, J. Am. Chem. Soc., 70, 1955 (1948) and Miartin-Smiith and Reid. J. Chem. Soc., 938 (10O6O). Thus, the compound of formula 60 can be obtained by heating intermediate V at reflux with chlorine, stannous and hydrochloric acid in acetic acid solution for 0.5 to 3 hours. The nnMrolbenzolithioiphenes of Formula 18 may be prepared by known methods as described by Bordwell and Sfcanige, J. Am. Chem. Soc, 77, 5939 (19iS5); Fries et al, Ann. 527, 83 (1936); and G. Karimow et al., Doki. Akad. Nauk Tadz SSR 13, 41 (1970), Chem. Abstr. 75; 5,605 I. 7-Aminobenzobibthiophenes of Formula 6 in Scheme 2, where R 1 is a hydrogen chloride, methyl, methoxy, chlorine or bromine atom, can be prepared as shown in Scheme 19, where R 1 is hydrogen arbs. "methyl, methoxy, chlorine or bromine group, Rio represents a hydrogen atom or a 1-3 carbon group alkyl group, and Ru represents a methyl group. The method shown in Scheme 19 includes three reaction steps: (1) heating to temperature the boiling under the reflux cooler of the corresponding 3- (phthalate) (H21Kiiitroienoyl) with an alphaHoroketone such as chioropropane in the presence of a base such as K3CQ3 in acetone, within 1 to 10 hours, to form an intermediate compound IN; (2) cyclization of this compound in polyphosphoric acid at a temperature of about 100 ° C. for 1 to 24 hours to form the 6- (substituted) -7H-nitrotoene [b] thiophene X; and (3) reducing the teigo of compound to give the compound of formula 6p. The reductions can be carried out by the methods described above in Scheme 18. The cyclization of thiotphenoxypropanones with the carbonation of the benzo [ph] thiophenes is known in the art, see the example of Karimow et al., Doki. Acad. Science of Tadzh. SSR, 13, 41 (1970), Chem. Aibstr. 75: 5605 h; and Yasuo Nippon Ragaku Zasshi 88, 758 (1967), Cliem. Abstr. 69; 59018 g. Also by replacing the alpha-chioroketone in Scheme 19 with chloroacetic aldehyde ethyl acetal or chioropropionaldehyde ethyl acetal and carrying out the reactions as described in this scheme, it is possible to prepare 7-amdnoibenzo [b] thiophenes of formula 6p, wherein Ri is as defined above, R10 is hydrogen or methyl and Rn is hydrogen. 4- and 7-aminoibenizo [; b] thiophenes of formula 6 in Scheme 2, where R 1 is SO 2 R 6, CO 2 R 5 or OSO 2 R 7, R 10 is a hydrogen atom or an alkyl group of 1-3 carbon atoms, and Ru is a hydrogen atom or a methyl group can be prepared by methods analogous to those described above in Scheme 5. Thus, starting from the appropriate 6Hchioro-7Hnitrobenzo [b] thiophene or 5Hchloro-4Hndtrohenzo [b] thiophene and carrying out the appropriate reactions described in Scheme 5, you can produce the compounds you want in formula 6! The starting 5-chloro-4-nitroibenzo [b] thiophenes and 6H-chloro-7Hniitróbenizio {ib] thiophenes are described above in Schemes 18 and 19, respectively. 4- and 7-aminoibenzo [b] thiophenes of the formula VI. in Scheme 2, where R 1 represents NOa or SO 4 NR 6 a, R 10 represents an alkyl group of 1-3 carbon atoms and R n is a methyl group *, can be prepared by the methods described in Scheme 6. Thus starting from the appropriate 4-or 7-acetamidobenzofb] thiophet and carrying out the nitration according to the methods described in Scheme 6, wherein R 1 is NO 2. Similarly, by carrying out the cMorosulfonation reactions of the corresponding 4- or 7-acetamidoibenizo [ib} thiophene, the desired 4- or 7-arninobenzo [Ib] thiophene of the formula 6 can be prepared in which R 1 is the group SOaNRsRg. The nitration of acetamidobenzolibithiophene is known in the art, see, for example, Bordwell and Stange, J. Am. Chem. Soc, 77, 5939. (1955). The chlorosulfonation of benzophythiophenes is also known in the art, see for example Paiier, Monatfch., 92, 677 (1961). 4- and 7-aiminofoenzo [b] thiophene 1,1-dioxides of formula 6 in Scheme 2, where Ri is a substituent other than CO2R5 or OiSO4 Rt, can be prepared from the corresponding 4- and 7-aminobenizo [ib ] thiophenes. The preparation involves three steps: (1) acetylating the amine with acetic anhydride to form 4- or 7-Hacetamidobenzo- [b] thiophene; 02) oxidation of this compound 3i08 / o with hydrogen peroxide to form 4-or 7-acetami-doibenzo [ib] thiophene-1, 1 -ylation of this compound to form 1,1- (4- or 7-aminobenjzo dioxide [ and b] itifene of formula 6. The acetylation step may be carried out at the reflux temperature of acetic anhydride with the addition of sulfuric acid as a catalyst by known methods. The oxidation step may be carried out in acetic acid at 50 to 115 ° C C within 0.5 to about 3 hours as described by Bordwell and Sibange, J. Am. Chem. Soc, 77, 5039 (1955). The deacetylation step may be carried out by hydrolysis with hydrochloric acid or saponification with sodium hydroxide by methods. as described in Scheme 6. Alternatively, some of the 1- and 7-amino-benzo [ib] thiophene 1,1H-dioxides of formula 6 described below can be prepared from the corresponding 4- and 7-nitrobenzo [b] thiophenes. : (1) oxidation of the nitro compound Wfi / o with hydrogen peroxide by the methods of description & nyimi pow more, with the formation of 4- or 7-nitrobenzo [b] thiophene 1,1-dioxide; and (2) reducing the nitro compound to form 4-. luib 7-aminotoenzo {b] thiophene 4Hd, in an oxide of formula 6. The reduction step may be carried out with liquid stannous chloride and hydrochloric acid in ethanol, such as. this is reported by Bordwell and AUbisetti, J. Am. Chem. Soc, 70, 1955 (1948) and Fries et al., Ann, 527, 83 (1937). The starting 4- and 7-nitropoenzo [pho] thiophenes have been described above. Using this method, it is possible to produce 1,1H-dioxide of 4- and 7-Haminobenzo [fo] thiophenes of formula 6 "wherein R 1 is hydrogen, chlorine, bromine, methoxy, SO2R6, CO2R5 or OSO2R7. 1,1-55 thiophenes of formula 6 in Scheme 2 (Qi = SO2) where Ri is a substituent other than CO ^ Rs, GSO4R7 or NOa may be prepared from the corresponding 4- and 7-aminobenzo [fo ] thiophene. The preparation involves four steps: (1) acetylating the amine with acetic anhydride to form 4- or N-acetimidobenzoyl-b] thiophene; (2) oxidizing this compound with 30% hydrogen peroxide to form 4-or 4-or 7-acetimido-benzp [fo] thiophene 1,1-dioxide; (3) reduction of this compound catalytically with 5% palladium on wood to form 4- or 7-aceiteimido-2,3-dihydrobenzolfo] thiophene M-dioxide; and (4) deacetylation of this compound to form the 4-or 7-amino-H 2 -Hdiihydrolbenzoi [to] * ester of the formula 6. The acetylation, oxidation and deacetylation phases can be carried out by the methods described above with respect to the preparation of 1,1- (4- and 7-arniinofoenzo [ib] thiophene dioxide. The reduction step is most preferably carried out at a temperature of &lt; 40 ° C under a pressure of X <013 to 039 mbar in an inert solvent such as ethanol. Catalytic reduction of 1,1-Hdioxides of benzo [Ib] thiophene to form 1,1-Hdioxides of 2y3nddihyidiroben! Zoljb] etcolphene is known in the art, for example, Bordwell and Stange, J. Am. Chem. Soc., 77, 5009 (19515) and Etordwell and McKellin, ibiid., 73, 325U (195) 1). Some 4- and 7-am% o ^, 3-dihydrobenizoi [! B) thdoiphenol-l, indwultienki The formula VI described below can be prepared from the corresponding 4- and 7-Hniitrobenzophytophenes. Starting from the corresponding 5-i / | substituted MH nitrobenizo [ib] thiophene or. 4- and 7-amino-2,3-dihydrobenzophenophenes of the formula 6 can be prepared by carrying out the reactions described in Schemes 17a and 17fo by 6- (substituent-, dihydrobenzo [ib} tdofen). wherein Ri is hydrogen, chlorine, bromine, methyl, methoxy, SO2U, CO2R8 or OSO * R7. The starting 5- (supplemented) Hnditrobenzo (b} thiophenes L 6- (substituted-N-dihydone). -7-nitirObenaa {'b] thiophenes are described above. In addition, 1- and 7-amino-2,3-dihydroxy The benza [ib] ittto-phene of formula 6, in which R 1 is a substituent other than OO4R5 or OSO2R7, can be prepared from the corresponding 4- and 7-amino-2-HdihydrobenjzoOTftdophenes. The preparation involves three steps: (ii) ) acetylated amine with ootic anhydride with the formation of 4- or 7-acetamd-to-2,3H-dihydrobenzo [b] thoiphene; (2) oxidation of this compound with 30% hydrogen peroxide in acetic acid at a temperature of 15 to BO ° C during 0.5 to about 5 hours, to form the 14 -dioxide of 4-or 7-acetamide, 3H-dihydrobenzo [ib] thiophene; and (3) deacetification of this compound to form the desired compounds of formula 6. Acetylation and deacetylation reactions can be carried out according to the methods described above for the preparation of 4- and 7-aminobenzo [b] thiolens 1,1-dioxides from the corresponding amdns. 4- and 7-aminobenzoA3- dihydrofoenzo-Jb] and ftoiphenes of formula 6 appearing in Scheme 2 (Qii-iSO), in which Ri is a substituent other than CC2R5 or OSOaR7., can be prepared from the corresponding 4- and 7-aminoH2 ^ -dihydrobenzo | b] t $ offens. The preparation includes the steps of: (!) Acetylating the amine with acetic anhydride to form 4- or 7-acetamidOH2, 3'-dihydro-benzo [b] -trophein; (2) oxidation of this compound with an equivalent mole amount of mnchioroperboenzoic acid to form 4-or 7-acetami'- to-2,3-dlihydrobenzo [b] itio [b] itio (phene; and (3) deaceitylation of this compound. to form the desired compound of formula 6. The oxidation step may be carried out in an inert solvent such as methylene chloride at a temperature of about 0 to 10 ° C for 1 to 16 hours as described by Johnson and Mc Canits. Jr., J. Am. Chem. Soc., 87, 1109 (1965) The acetylation and deacetylation stages can be carried out by the above-described methods 4- and 7-amino-benzofurans, 4- and 7-aminobenzo [b] -5 thiophenes and The 4-and 7-aiminofoenzo [b] -thiophene 1,1-dioxides of formula 6 appearing in Scheme 2, in which R10 or Rn is chlorine or bromine, can be prepared by known methods for halogenation reactions. Prepared by: (a) heating the appropriate 4- or Tracetamido-1-benzofuran-, benzofb] -thiophene or the 1- or 1- or 4- or 7-Hacetamidite dioxide enzo (jb] thioiphene with chlorine or bromine at a temperature of about 10 to 60 ° C for a period of 5 to 5 hours in an inert solvent such as chloroform or acetic acid, followed by (b) deacetylation of the resulting halogenated the product using one of the methods previously described in Scheme 6. The amines of Formula 3 in Scheme 1 are intermediates for the preparation of the compounds of Formula 1 in the process of the invention. The pyrimidines and the thorizines are formulas 3a to 3d in which G "X, Xi, Y, and Z are as defined above, except that Y is a substituent other than GH (OCIHa) or the group of formula 47, are either known or can be obtained by conventional methods. . Thus, for example, the synthesis of pyrithmidines and triazines of general formula III has been extensively discussed in The Chemistry of Heterocyclic Compourtds, a serial publication by Interscience Bubidshers, Inc. New York and London. 2-aminopyrimidines are described by D. J. Brown in The Pyrimidihes, Vol. 16 of the above series, while the 35 and Ldys of 2-amino-yl, 3,5-, triazines are described by E. M. Smolin and L. Raipaport in s-Triazfines and Derivatives; bar 13 of the above series. Triazine syntheses are disclosed in US Patent 3,164,547 and are described by K. R. Hiufiflman and F. C. 40 Schaefer, J. Org. Chem., 28, 1812 (1963). The syntheses of the bicyclic amines of formula 3® and 3d are described in EP-A-016,663 and EP-A-3b in EP 46 677. 45 The pyrimidines of formula 3e in which Y is GHtfOC & ld * are described by W. Braker and in., J. Am. Chem. Soc., 69,3t072 (1947); Portions of this description are provided herein for purposes of illustration. Using the techniques described by Braker, or their respective modifications * obvious to those skilled in the art, it is possible to prepare pyrimidines of formula 3e in which X is methyl, methoxy or chlorthi and Y is CHi (OCiHs), or a group of formula 47. 56 The triazines of Formula IIIf can be prepared according to the methods shown in "Schemes 20 and 21, wherein X is a methyl or methoxy group and Y is an OH / OGH2 group or a group of formula 47. Reactions shown in Scheme 60 20a) is carried out as described by JM McElvain and RL Ciarke, J. Am. Chem. Soc., 69, 2657 (194) 7) which describes the preparation of ethyl diethoxyiminoacetate. The N-cyanimidate intermediate of formula 22 can be prepared as is a description of - • 5 room D. Lwowski, Synthesis, 1971, .2 © 3, as a result of the 142 m 25 reaction of the compound of formula 21 with cyananasnide at pH 5.5, and then a condenser according to the reaction of 20c with acetamidine or O ^ ethylphiUrea in alcoholic acid solvent at temperature e 25 to 80 ° C, leading to the formation of the corresponding 5 fcriazines. Alternatively, the reactions of Scheme 21a, as described for the substituted acetonitriles, by PC Schaefer and GA-Peters, J. Org.Chem., "26, 412 (1961), can be used to convert the nitrile of formula 20 to the corresponding iminoester. Reactions 21b and 21c can be used as a free base, or alternatively converted into an amidinium hydrochloride of formula 23 as described in said publication and condensed with methyl N-cyanoacetamidate or with dimethyl N-cyanimide glaam. in the presence of one equivalent of sodium methoxide to give the triazines of formula 31. Cyclic acetals of formula III and can also be prepared from compounds of formula III by acetal exchange as shown in Scheme 22. wherein X is methyl or methoxy and Z is CH or nitrogen The reaction of Scheme 22 is carried out by heating the aliphatic acetal in an inert diluent in the presence of one carbon equivalent ethylene glycol and slightly more than one equivalent of ethylene glycol and slightly more than one equivalent of strong acid, such as p-toluenesulfonic acid, with continuous removal of M methanol or ethanol formed in the reaction by distillation. The product is isolated by treatment with an aqueous base and extraction with an organic solvent, and is purified by crystallization or by column chromatography; Methods of making 3 Hamino ^ lj2,4- (triazDlfi of formula 3 appearing in Scheme 1 are complex in the art, and a review of the chemistry of lA4- | triazoii is contained in The Chemisitry of Hefterocyclic Com- * ° pounds— Triazoles 1,2 , 4 (John Wiley and Sons, New York, 1961). Commonly used nitrogen-containing starting materials include N-aminoguanidine, hydrazine, alkylhydrazines, cyanamide, ethyl cyanoacetimphidate, dimethyl cyanedithioimido carbonate, dimethyl cyanide. , ethoxymethylene cyanamide and acylhydrazines. Some of the syntheses reported in the literature are illustrated below, "By using these techniques or suitable modifications obvious to those skilled in the art, 3-amino, 4- * intermediate riazoie can be easily produced. the amounts of ethyl propionimidate hydrochloride and N-aminoguanidine nitrate in pyridine lead to the formation of 3R 55-amino-S-ethyl triazium as shown in Scheme 24; RPN Patent No. 1973,499; Berichte, 96, 106 4 (1963). Condensation of hydrazine with ethyl N-cyanoacetamidate will lead to the formation of 3-amino-5-methyl-60thiazole as shown in Scheme-25; Journal of Organic Chemisitry, 2S, 1816 (1960). U.S. Patent No. 2-836,581 (19S8) discloses the preparation of 3-amino-5Vhydroteymethyl triazole from N-amino-5 giuandidine and glycoic acid. and the British Patent No. 7,361,566 (1056) describes the synthesis of 3 Hamino-5HmerkQptio, as shown in Scheme 26. Condensation of hydrazine with cyanodithioltm, cte-, dimethyl carbonate in acetonrotrile, leads to the formation of 3-amide. Methyl-1A ^ ^ ribol, while the reaction of the hydrazine with dimethyl N-cyanimide carbonate leads to the formation of &lt; -amino &lt; &gt; Hmethexyl, 2,4H-triazole as shown in Scheme 27; Journal of Organic CAemistry, 39, 15122 (1974). , •; Reactions of substituted hydrazines with N-cyanothio- / imido carbonates (prepared as described in DM Wielamd, PhD thesis, 1071, pp. 123— 124V is used to prepare bisubstituted aimimoitriazals as shown in Scheme 26 in where Yj is a metal or ethyl group. Many of the amino heterocyte intermediate compounds of Formula III in which R is methyl can be prepared in a two-step process as described for compounds of Formula III and Scheme 23 in which X, Y and Z have the meanings given above, and R is a methyl group. A solution of the amine compound of formula 24 in concentrated hydrochloric acid is treated with a sodium nitrite solution and the chlorine compound of formula 26 is isolated in the usual manner by filtering off the acidic solution. A representative process is described by Ree. and Rose, J. Ghem. Soc. C, 2031, (1966), for the case where Z is CH and X and Y are methoxy. The displacement of chlorine from the compound of formula 25 can be performed by by heating with an excess of methylammonium in water to give the methylamino heterocyclic derivative of formula III. The agriculturally acceptable salts of the compounds of Formula I are also useful herbicides and can be prepared using a variety of methods known in the art. Thus, for example, metal salts can be prepared by treating compounds of Formula I. metal hydroxide or salt solution. alkaline earths having a sufficiently basic anion (for example, alcoholate hydroxide, carbonate or hydride). Quaternary ammonium salts can be prepared in a similar manner. The strengths of the compounds of formula I can also be prepared by exchanging one kajion for another. The exchange of cations can be carried out by directly treating an aqueous solution of a salt of a compound of formula I (for example an alkali metal salt or a quaternary ammonium salt) with the solution containing the cation to be replaced. The method is most effective when the desired salt containing the exchanged cation is it is insoluble in water, for example it is a copper salt, and it is otherwise separated by filtration. The exchange of a kajbion can also be accomplished by passing an aqueous solution of a salt of a compound of formula I (for example an alkali metal or quaternary ammonium salt) through a column filled with Cartionite resin, containing $ a- \ • which cation, for stench-is to be px ^ € ^ ow ^ dtabna142 685 27 28 exchange. In this method, the resin cation is exchanged with the original salt cation and the desired product elutes from the column. This method is particularly useful when the desired salt is water-soluble, for example, potassium, sodium or calcium. Acid addition salts as active ingredient compounds of the agent according to the invention can be obtained by reaction. a compound of formula I with a suitable acid, such as, for example, pH-toluenesulfonic acid, trichloroacetic acid or the like. The herbicidal compositions according to the invention containing the compounds of formula I as active ingredients can be prepared in a conventional manner. They can take the form of dusts, granules, tablets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, etc. Many of them are suitable for direct application. shade in suitable environments and apply with spray volumes ranging from a few liters to several hundred liters per hectare. The high concentration compositions are mainly used as intermediate materials for the further preparation of herbicides in a useful form. In general, the inventive agents contain 0.1 to 09% by weight of one or more active ingredients and at least one of such additives as (a) about 0.1 to 20% of one or more surfactants, and (b) about 1-99.9% solid or liquid of one or more diluents. More closely, the agents according to the invention contain the above-mentioned substances in the proportions listed below in Table I. Table I 40 45 50 55 v 1 Wettable powders Oil suspensions, emulsions, solutions (including emulsifiable concentrates) Aqueous suspensions • Dusts Granules and tablets \ Compositions high concentration Active substance 20—90 3 ^ 50 10- ^ 50 1—25 0.1—05 00—90% by weight 'Thinner (s) 10-74 40 ^ 95 40-84 TO —99 t) Ala, "0-10" Surfactant (s) 1-ylO ^ and 0-45., 1-io '1 & -15 0 ^ 15 0 ^ 2 \ * Active substance plus at least one such additive, How the entrainer or diluent together make up 100% by weight. 65 The agent of the invention may, of course, contain smaller or larger amounts of active ingredient, the amount being determined depending on the intended use and the physical properties of the compound. there are higher ratios of the amount of surfactant to the amount of active ingredient; this is accomplished by incorporating an appropriate amount of surfactant into the formulation or by tank agitation. Typical steels are described in Watkins et al., "Handbook of Insecticide Dust Diluents and Carriers"; 2nd edition, Dorland Books, Caldwell, New Jersey; however, other solid, fossil or manufactured substances may also be used. Higher absorptive diluents are more advantageous for wettable powders, while higher densities for dusts: Typical liquid diluents and solvents are listed in Marsden, "Solvents Guide", 2nd edition, International Science, New York. , 19-50. For concentrates, a solubility of less than 0.1% is preferred; the solution concentrates should preferably be stable to phase separation at 0 ° C. In McOutcheon, Detergenits and Emulsifiers, Annuai, MC Puiblishing Corp. ., Ridgewood, New Jersey, and Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, "surfactants" are listed and their contents are indicated. application. The compositions according to the invention may all contain small amounts of additives for anti-foam, caking, corrosion, microbial growth and the like. The methods for making such compositions are well known. Solutions are prepared by simply mixing the ingredients together. The fine-grained solid preparations are prepared by mixing and usually grinding, for example in hammer mills or fluid mills. Slurries are prepared by "wet milling (see, for example, U.S. Patent No. 3,060,084). The granules may be prepared by spraying the active ingredient onto pre-prepared granular carriers or by agglomeration techniques, see for example JE Browning," Agglomeration ". ", Chemical Engineering, 4 December 1967, pp. 147 ff. And" Ferrite Chemical Engineer ^ Handbook ", 5th Edition, McGraw ^ Hill, New York, 1973, pp. 8 ^ 57 and, for further information. the subject of making utility preparations can be found, for example, in the following publications: IL M. Loux, United States Patent No. 3 23-5 361, col. 6, line 16 - col. 7, line 19, and examples 10-41; RW Duckeaiijbaugh, United States patent specification No. 3,309,192, col. 5, line 43 - 'col. 7, line 62 and examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-1140, 162-464, 166, 167, and 169-182; H. Gysin and E. Knusii, U.S. Patent No. 2,891,855, col. 3, v. 66 - col. 5, v. 17 and examples 1 ^ 4; CCKlingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1061, pp. 81-96; 29 142 685 30 and JD Fryer and SA Evans, "Weed Control Handibook", 5 wyidamie, DlackweM Sniemtific Puiblicitions, Oxford, 1968, pp. 101-103. The compositions according to the invention find use as very potent herbicides. They are used extensively for pre- and / or post-emergence weed control in areas where all vegetation is desired, such as oibsis around fuel tanks, ammunition depots, industrial warehouses, parking lots, open air cinemas with car entry, around advertising boards, and highway and railway structures. Alternatively, the agents of the invention may be used to regulate plant growth. The dosages of the agents of the invention depend on a number of factors, such as whether or not they are applied. them as herbicides or regulating plant growth, type of crops, types of weeds to be controlled, weather conditions, selected utility preparations, method of treatment, number of leaves, etc. In general, it can be stated that the compounds according to the invention should be used in an amount of about 0, 05-10 kg / ha, with the lower doses recommended for use on lighter soils and soils with low organic matter content, or in situations where the presence of this agent is required for a short time, or when regulating plant growth. The compounds of formula I can be used in combination with other industrial herbicides, such as compounds of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylic salts type compounds. in trials conducted in greenhouses. The method of conducting the research and the results are given below: A test of the growing medium, seeds of bloodstain (Digitaria sp.), One-sided weed (Echinochloa cruisgalli), gluche go oats (Avena fatua), cassia (Cassia obtusifolia) were planted, morning glory (Ipomea sp.), rapenia (Xanthium pemsyl-, vanicuim), sorghum, maize, salt, rice, sugar beet, wheat and chrysanthemum tubers (Cyperus rotundus), after which they were treated with North-East research compounds dissolved in non-toxic a solvent for plants. At the same time, treatments were performed on the same useful crops and on weeds, as well as on cotton and bush beans, by spraying the soil and leaves with solutions of the tested compounds. At the time of the treatments, the height of the plants was in the range from 2 to 18 cm. The treated plants and control plants were kept in a greenhouse for 16 days, after which the test plants were compared with the control plants and their responses to treatment with test compounds were visually assessed. The ranks listed in Table II are based on a numerical scale ranging from 0 - no operation to 10 - complete failure. The symbols associated with the numerical evaluation have the following meanings: A = growth acceleration, C = chlorosis or necrosis, D = leaf loss, E = inhibition of plant growth, G = growth retardation, 5 H = effect on growth zones, U = extreme color , X = stimulation of the leaf groin zones, and- '6Y = bud fall or flower buds. As can be seen, the test compounds show high pre- and post-emergence activity at the low doses selected for this evaluation. Some compounds, for example compounds 127, 130, 147, 140 and 155, showed low activity at the very low application rates selected in this test, but it can be assumed that these compounds would have shown higher activity when using higher doses. ib 1 ica II iZdrug of formula 20 52 53 54 Dose, fcgi / ha 0.05 0.05 0.05 Post-eastern bush beans 3C, 8G, 6Y 6C, 9G 6C, 9G, 6Y 25 cotton 3C, 3H, 9G 6C, 9G 6C, 9H morning glory 2C, 9G 3C ,. 9H 6C, 0G turnip 5G 10C 9C cassia IC, 5G 6C, fJG 4C, 8H ^ cibora 4G 6C, 9H 2C, 8G 30 bloody tusk * 4G 6C, 9G 2C, 7G. one-sided weed 2C, 9H 10C 10C deaf oats' 2C, 6G 7C, 9C 5C, 9G 35 40 45 50 55 60 65 wheat maize soybean rice sorghum beetroot. sugar Before-. eastern bindweed turnips "cassia <cibora paiusznik bloody weed one-sided deaf oats wheat maize soybean rice sorghum sugar beet dose, kg ^ ha Post-East bush beans 2C, 6G 2 € 8H 3C, 9G, 2C, 9H 3C, 9H - 2C, 6H 8H 6G 3G IC 4C, 9H 2C, 9H IC, 9G 2C, 7G * 2C 2C 2C, 8H - 55 0.05 5rC 2C, 9G iOC 5X 5C, 9G 5C, 9G 5C, 9G. - 8G 9H 7G 10E 2C, 6G 5C, 9H 4C, 9H 9H 10H 9H 10E 5C, 9G. - Compound with 56 0.05 9C 6C, 9G 3U, 9G 4C, 9G iC, SG 9G. - 9G 9H 2C, 7G 2C, 9G 2C, 8G 6C, 9H 3 €, 9H 9G-% 5C, OH 9H 5C, 9H 4C, 9H - formula 67 0.06 3C, OG, 6Y31 142 685 32 cotton cassia bloody weed weed weed weeds one-sided deaf oats wheat maize soybean rice sorghum sugar beet Pre-eastern reason turnip cassia tibora bloody weed weeds deaf oats wheat maize v soybean rice sotrgo sugar beet Dose, kg / ha 6C, 9G 7H 9C 4C , 8G 9C 6C, 9G 9C 10C 9C 6C, 9G 9C - 9G 9H 5C. 9G 5G 3C 6G 5C, 9H 4C, 9H 2C, 9G 5C, 9G 9H 10E 7C, 9H - 9C 9C 10C 2C, 8H 3C, 6G 2C, 8G -9C 9C 10C 10C 9C 6C, 9G 10C - 9G 9H 5C, 9G 2C, 7G 3C, 7H 5C, 9H 4C, 9H 2C, 9G 10G 9H 10E 6C, 9H - 2C, 2C 2C 2A 0 0 2C, 1C 0 2C, 2C, 6G 2C, - 2C, 2C, 1C 0 0 2C, 2C, 1C 4C, 1H, 4C, 4C, - Compound of formula 58 0.05 0.4 0.05 5G 7H 8H 5H 8H 5H 9H 7H 8G 7H 1A 7H 8H 59 Dose, kg / ha Post-East bush bean cotton bindweed cassia chrysanthemum bloody weed weaver deaf oats wheat maize soybean rice SOTgO sugar beet Post-eastern bindweed cassia tibora 0.05 5C, 9G, 5C, 9G 4C, 9G 3C, 9G 3C, 8G 9G 4C, 9G 9C 9C 9C 4U 9G 4C, 9G 9C 5C 9C 9G 3C, 8H 3C, 7G 3C, 8G 0.4 6Y 9C 9C 10C 9C 10C 5C, 9G 6C, 9G 9C 6C, 9G 9C 3U, 9G 9C 5C, 9G 5C, 9G - 9C 9H 9G 10E 0.05 9C 9C 9C 10C 9C 9G 5C 5C 6C 6C 5U 9C 5C 4C - 9G 9H 9G 10E 15 20 25 30 35 40 45 50 55 bloody weed weed deaf oats wheat maize soy rice sorghum sugar beet 3C, 7G 3C , 8H 5C, 9G 3C, 9G 2C, 9G 3C, 6H 10E 3C, 9G 3C, 9G 10E 9H, 7C 6C, 9H 10E 10H 9H 10E 10E 10E 60 Dose, kg / ha 0.4 East bush bean cotton 8C bindweed 9C turnip 10C cassia 9C cibora 9C finger 9C bloody 7C, 9G one-sided weed 9C deaf oats 6C, 9G wheat 7C, 9G kuku- Compound of formula 9C 9C 6C, 9G 9C 9H 9H 9G, 4C 10E 65 rice soybean rice sorghum sugar beet evidence of morning glory cassia tibora blood finger 6C, 9G unilateral weed 6C, 9H deaf oats 6C, 9H wheat 6C, 9H corn 10E soybeans 9H 0.05 0.4 5C, 9G 6C, 9H 6C, 9H 10E 10E 9H 10E 6C, 9H 10E 61 0.05 6C, 9G, 6Y 9C € 6, 9G, 6Y 10C 4C, 9G 5C, 9G 10C 40, 9G 3C, 7H 9C 5C, 9G 4C, 8G 9C 5C , 9G 3C, 7G 9G 2C, 8G 0 7C, 9G 7C, 9G 6C, 9G 6C, 9G 9C 9C 5C, 9G 5C, 9G 4C, 9G 2C, 8G 9C 9C 6C, 9G 4C, 9H 6C, 9H 9C 7C, 9G 4U, 9G 9C 3C, 7G 5C, 9G "4C, 9G 2C, 9G 2C, 9G • 5C, 9G 9H 5C, 9G 10E 5C, 9G 5C, 3H 5C, * 9H 5C, 9H 5C, 9G 9H 9G 9H 9G 2G 2C, 5G 5H 7G 1C, 3G 2C, 6G 2G 3C, 9H 4G 3C, 8H 5C., 9H 5C, 9H 2C, 8H 2C, 6G yG 2C, 8G] C, 1H33 142 685 34 ream 10E sorghum 10E sugar beet 10E 62 Dose, • kg / ha 0.4 East bush bean 9C cotton 4C, 8G morning glory 9C turnip 4C, 9G cassia 5 ^, 9G ciibotra 7G blood stick 4C, 9G monosided weed N 4C, 9H deaf oats GC, 9G wheat 4C, 9G corn 3C, 9G soybeans 9C rice ^ f 0G sorghum 2C, 9G sugar beet - Pre- East morning glory 9G turnip 9H cassia 9G cyprus 5G bloodworm 2C, 6G single-sided weed 3C, 9H deaf oats 2C, 8H wheat 9G corn 2U, 0G soybean. 2C, 8H rice 10E sorghum 4C, 9H sugar beet 10E 66 Dose, kgi / ha 0.4 10E CC 9H '9E Compound 63 0.05 9C 5C, 9G 5C, 9G 9C 4C, 9G 4C, 8G 5C, 9G 5C, 9H 9C 9C 5U, 9C 9C 5C, 9G 5U, 9C 9C 9G 9H 5C, 9G 10E 5C, 9G 4C, 9H 4C, 8G 9H 5C, 9H 8H 10E 5C, 9H 10E 10E 10H 10E 10E 9H 6G with a 64 * 0 visor , 05 9C 6C, 9G ¦9C 9C 9C 10C 9C 6C, 9H 9C 9C 10C 9C 6C, 9G 9C 9C 9C 9H 2iC, 9G 10E 6C, 9H 6C, 9H 6C, 9H 9H. 9H 2C, 8H 10H lOE 65 0.05 9C 5C, 9G 9C 10E 9C 6C, 9G 7C, 9G 9C 9C 9C 9C ^ »6C, 9G 9C 9C 9C 9H CG 1CE fiC, 9G 6C, 9H 5C, 9H 9H 9H 9H 10E 6C , 9H '.0E Compound of formula 0.05 0.4 67 0.05 5 • 10 15 20 25 30 35 40 45 50 55 60 65 East bush bean "C cotton * C" ® G morning glory 9C turnip 9 ^ cassia ^ cassium 3C 9G paiusz; - bloody weed ^ one-sided weed 9C deaf oats 9C wheat 9 ^ corn * 0C soybean ^ C, 0G rice ®C sorghum * ^ sugar beet 9C Fore-east - downy morning glory 9C turnip 9H cassia 9G chibora 10E bloody finger 5C, 9G one-sided weed 6C, 0H deaf oats 6C, 9H wheat and 10E corn 10E soybeans ®H rice 10E sorghum 7C ,,, 9H sugar beet 10E 68 Dose, kg / ha 0.05 East bush bean 1C cotton 1C, 2H morning glory 2C, 3 (G 9C 5C, 9G 4C, 8H 4C, 9H 5C, 9G 3C, 9G 4C, 8G 9C 9C 8U, 9G 9C 5C, 9G 9C 6C, 9G 9C 9G 9H 9G 2G 7G 3C, 8G 4C, 9H 5C, 9H 5C, 9H 8H 10E 5C, 9H 10E 9C 4C, 9G 5C, 9G 9C 9C 9G 7- C, 9G 9C 9C 9C 9C 6C, 9G 9C 9C. 9C 9C 9H 9C 10E 7C, 9G 6C, 9A 6C, 9H 6C, 9H 10H 9H 10E 7C, 9H 10E. 6C, 9G, 6V 4C, 9G 4C, 9G 5C, 9G 5C, 9G 2C, 8G? C, 8G 9C 9C PC 7U, 9C 5C, 9G 9C 6C, 9G PC 9G 2C, 8H 9G 5C, 9G 2C, 6G 5C, 8G 5C, 9H 9H 5C, 9H 8H 10E 5C, GH 10E Compound of formula 69 0.05 10D, 9G, 6Y 4Q 9G 2C, 8H 70 0.05 71 0.05 9D, 9G, 6Y 0 4C , 9G 3C, 9G 0 035 142 685 36 turnip cassia tibora bloody weed weeds deaf sheep wheat corn soybean rice sorghum sugar beet early morning morning glory cassia cibora bloody weed weed one-sided deaf oats wheat corn soybean rice sorghum beetroot 2G 0 0 0 3G 0 0 0 0 5G 1C 2G 0 0 0 0 0 0 0 0 0 0 0 0 sugar 2C Dose, kg / ha East beans Bushy cotton bindweed turnip cassia tibora bloody weed weed 0.0E fc 72 2C, 9H 2C, 8H 2C, 8G 3C, 9G 9C 2C, 9G 19E 5U, 9G 3C, 9G 5C, 9G 5C, 9G OC 9H 9H 8G 2C 2C, 3H 5C} 9H 5C, 9G 10C 2C, 9H. 3C, 8H 5C, 9H 5C, 9H 5C, 9G Compound 73 0.05 4C, 9G, 6Y bC, 8G. 6Y 3C, 5C, 5C, 2C, 2C 2C, 4G 8H 9H 4H 7G 4C, 8G 4C, 9H 4C, 8H 3C.v3H 0 2C, 8G 5C, 9G 6C, 9G 9C 9C 9C ¦6C, 9G 9C 10C 50, 9G 90 10C 9C 5C, m 9H 9G 10E 2C, 6G 5C, 9H 5C, 9G 6C, 9H 9C 9H 10E 5C, 9H 9C 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 i0 0 0 0 0 0 formula 2.0 74 0.05 3C, 5G, 6Y0 4C, 8G 4C, 8G 4C, 9G 3G 2G 2G 0 0 0 0 0 0 5 10 15 20 25 30 35 40 45 50 55 80 «one ¬ deaf oats corn corn soybean rice sorghum sugar beet Pre-eastern bindweed cassia cibora red weed weed deaf deaf oats wheat corn SOJfk sorghum rice sugar beet Dose, kig / ha Po- Eastern bush bean cotton bindweed cassia tibora bloody weed unilateral deaf oats wheat cucumber 5 ua 9C 80 9C 7U, 9C 90 90 10C 90 40.80.5X20, 9G 6C, 9G 5U, 9C 5C, 9G 30, 8H 9H 20, 7G 0 1H 2C, 5G 2C, 9G 2C, 9G 3C, 9H 20, 3H 10E 50, 9G 10 75 0.05 50, OG 90 90 9G 50, 9G 20, 3H 0 0 6H 20,9G 20,9G 50,9H 10,1H 10E 50,9H 4C 8G Compound 76 0.05 30.9G, 6Y 70, 9G, 6Y 3C, 4H, 9G 40, 4H, 9G 30, 9G 30, 9G 2C, 5G 3G 0 2C, 5H 2G 8G 30, 9G 30, 9G 3C, 8G 30, 9G? C, 8H 3G 2H 6H 0 4G 20, 9G 3H, 9G 0 0 5G, 3H 1C, 20, 2C, 2H 8H 10 0 0 4G 5G 4G 50, 2G 0 SC, 5X 5G 5G 7H 8H 7G 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2G 3 0 2G with formula 2.0 0 0 0 0 0 0 0 0 0 0 0 0 0 OM 0 0 0 0 0 0 0 0 0 0 0 037 142 685 38 rice sorghum sugar beet Northeast bindweed cassia tibora bloody chasrf; - single-sided deaf oats wheat corn soybeans sorghum sorghum sugar beet Diwka, kg / ha South East beans shrub tufted cotton bindweed turnip cassia cdbora bloody weed weed one-sided deaf oats wheat corn soybean rice sorghum sugar beet East East morning glory 3C, 9G 3C, 9G - 2 €, 8H 8H 0 0 2C, 4G 6H 2G 7G 2C, OH 2C, 6G 3C, 7H 4C, 8H - 78 0.4 6C. 9G 9G - 2C, 8G 9H 3C, 8H 2C, 6G - IC 2C, 7H 2C, 8H 2C, 9G 2C, QG 2C, 6H 9H 3C, 9G - 0 0 - 0 0 0 0 0 0 0 0 0 0 0 0 - 0 0 - 0 0 0 0 3G 3G 0 0 0 0 0 0 - (Relationship about visorae 0.05 5C, 9G, 6Y2C, 2H 4C, 8G 3C 2C, 5H 3C 2G 2G 2C, 7H 9G, 7X 10C 9C 2H , 5G 9iC 9C 2C, 4G IC IC IC IC 0 0 0 4G, 5X IC, 5G 2C, 7H IC, 1H 2U, 9G 2C, 9H - 0 2.0 79 0.05 6C, 9G, 6Y1C, 3G 2C, 3H, 8G1C 5C, 9H 2C "5H 3C, 4H 0 IC, 3G 5C, 9H 5C, 9G 9C 6U, 9C IC, 5G 9C 2U, 9G - ¦ 8G IC 0 IC 0 .0 0 0 0 0 0 0 0 0 10 15 turnips 1H cassia 0 cibora 0 bloody weed 0 mono weed 2G giucha oats 5iH wheat 8G corn 3C, 9G soybean rice sorghum sugar beet - 0 9G, «E 2C, 9G 25 W 40 45 50 55 Dose, kg / ha 0.4 East bush bean IC cotton IC morning glory IC cassia 0 cyprus 0 kirvivi leaf 2G single-sided weed IC coarse oats 0 wheat 0 corn 0 soybeans 0 reams 0 sorghum 2C cutar beetroot Mid-eastern bindweed 0 turnips - cassia cibora bloody IC chasit- ndca 0 10E 8H 8G. 8G 2G 2G 2G 2G 2G 0 0 2C, 5G 1H 2G IC, 4G 2C, 8G 2G 2C, 8G 0 2C, 9G 0 2C, 9G 0 IC, 2H 2G 5C, 7G 0 3C, 9G 0 0.4 Compound of formula 81 62 0.4 0.4 4C, 9G, 6Y 5C, 9G 4C, 8H 5C, 9G 2C, 3H 2G 4G 2C, 8H 0 3G 3C, 7G 4C, 8G 4C, 9G 5C, 9G 9D, 9Q, 6Y0 5C , 9G 4C, 6H 3C, 9G 3C, 8G 2G IC, 3G 0 10C 3G 5G 2C, 9H 0 5C, 9G 0 6C, 9G 0 9G 0 9G 9H 2C, 8G 10E 2C 9G 8H 9G 10E 4G142685 40 Single-sided IC deaf oats 2G wheat 0 corn 2C, 5G soybeans rice sorghum sugar beet - 0 IC 2C, 3G 2C, 9H 2C, 6G 9G 2C, 9G 2C, 6H 10E 3C, 9H 5C, 9H 0 2C, 6G 0 9G 0 2C , 9G 0 9H 0 10E 0 10H 0 84 Compound 85 of formula 86 87 Dose, kg / ha Southeast bean bush cassia tibora bloody weed weed deaf oat wheat corn ¬ rye soybean rice sorghum sugar beet Pre-eastern bindweed cassia cibora bloody weed single-sided deaf oats wheat corn soybean 0.4 0.05 4C, 9G, 6Y 5C, 9G 2C 2C 2C 0 9C 4C, 9G 5C, 9G 9C 5C, 9G 5C, 9G 2G 2H 3G 2G 4C, 8H 5C, 8G 3C 9C 2C, OG 9C 9C 9C 9C 9C 5C, 9G 9C 9C - 9C 2G 9H 2C, 6G 0 2G 9G 8H 9C 9G 4C, 8G 2C, 7G 9C 3C 2C, 9H 2C, 9H 2Ct 3H 4C, 9G 9C 9C 4C, 8H 0.05 0.05 9C - 5C, 9G, 6Y 4C, 9G 4C, 8G 9C 4C, 7G 10C 10C 9C 4C, 8G 9C 2G / 6C, 9G IC, 3G 9C 9C 9C 9C 9C 9C 9C 4G, 9H 2C, 8G 8G 5U, 9G 5C, 9G 6C, 9G 3C, 9G 5C, 9G rC, 9G 10C 9C 9H 9H 3C, 9G 8G 10E 2C 5C, 9G 2C, IG 9H 3C, 6H 5C, 9G 2C, 0G 10C 2C, 8G 5C, 9G 3C, 9H 3C, 8H 2C, 7H 10 15 20 25 30 35 40 45 50 55 60 65 ream 10E sorghum 5C, 9G sugar beet - 10E 9H 5C, 9G Compound 89 10E 10E 6C, 9H 5C, 9H 5C, 9G 10C of formula 90 91 Dose, kgtfha East bush bean 0.05 0.05 cotton 4C, 8H bindweed 3C, 7G turnip 9C Cassia 3C, 8G Tiberia 3G 5C, 9G, 6Y4C, 6G, 6Y 4C, 7H 4C 3C, 8H 2C 2G blood vessel 3G unilateral weed ^ 9H deaf oats "* C, ^ G wheat 2C, 9G, 5X2C, 8G kuku- 3U, 9G 5C, 0G 5C, 9G 2C, 9G rice soybean rice sorghum sugar beet ^ Pre-eastern bindweed cassia tibora blood stick 1 ^ - »2G * weed weed itronical deaf oats 2C, 8G wheat IC, 5G cuckoo - 1C 4C, 9H 2C9 6G 2C, 8H 2C, 8G 5C, 9G 4C, 9H 9G 9H 9G 2C 4C, 9G 2C, 8H 4G 4G 2G 0.06 0.05 corn soy rice sorghum sugar beet 10E 2C, 9H 2C, 6G 10E 4C, 9G 5C, 9G, 6Y4C, 8G, 6Y 4C, 9G 4C, 7H 3C ,, 8G 4C 9G 9C 3C, 9H 4C, 6H 2C 4C, 9G 0 2C , 8G IC 9C 3C, 9H 9C IC, 3G 9C IC, 5G 4U, 9C 2C, 9G 4C, 9G 4C, 9G 6C, 9G 6C, 9G 9C 2C, 9G 9C 4C "8G 9G 3C, 8G 9H 9H 2C, 4G 2C, 5G 10E 0 2G IC Dose, kg / ha 3C, 8EL 3C, 9H 4C, 9H 5C, 8H 2C »8G 2C, 9G 3C, 7G 2C, 9G 2C, 9H 7G BC, 9H 2C, 9H 2C, 9G 2C , 3H 2C, SH 3C, 6H 5C, 9H 10E 10E 3C, 9H 2C, 9H 2C, 9H 9G 4C, 9G 4C, 9G visor 94 95 and 0.4 0.4 0.4 Compound 93 0.0541 142 685 42 South East bush bean bush bindweed cassia cibona bloody weed weed deaf oat wheat corn soybean rice sorghum sugar beet East eastern bindweed cassia ciibora paiusz- ndk bloody weed- mono-sided deaf oats wheat corn soybean rice sorghum sugar beet Dose , kg / ha. East bush bean cotton bindweed 4C, 9G, 6Y <5C, 9G, 6Y 2C, 2H 4C, 8H 4C, 9H 2C, 3H 0 2C 4C, 8H 3C, 9G 2C, 5G 1U, 9G 3C, 9G 5C, 9G 2C, 9G 3C, 9H 8G 8H 7G 2G IC 4C , 8H 2C, 8G 2C, 7G 2C, 9G 2C, 4H 10E 2C, 9H 3C, 9G 96 0.4 i5C, 9G ¦10C 10C 90 9G 5C, 9G BC, 9H -5C, 9H 4C, 9G 3U, 9G 9C ¦5C, 9G 2U, 9G 9C 9G 9H 9G 10E 10E '5C, 9H 5C, 9H 9H 9H 9H 10E 10E 10E Compound 97 0.4 4 € J4G “6Y0 2C 0 0 ¦o 9C 5C, 9G 4C, 8G 9C 9C 4C, 9G 5C, 9G 9C 4C, 9G IC, 7G 4U, 9G 9C 5C, 9G 3C, 9G 5C, 9G 9G 9H 90 10E 5C, 9G 5C, 9H 4C, 3G 8G 3C, 9G 9H 10E 5C, 9G 10E 2C 2C, IC 3C, 2C 2G 0 0 0 0 0 2G 0 0 8G 8H 5G 5G 0 3C 0 0 3G 2C -2C, IC formula 98 0.4 0 0 0 0.4 6C, IC nct 2H 7H - 5G - 99 9G, 6Y 2G 5 10 15 20 25 30 35 40 45 50 55 60 65 cassia turnip cibara bloody weed single-sided deaf oats wheat maize rice sorghum sugar beet East eastern bindweed cassia c; bcxra bloody haemophilia deaf oats wheat corn soybean rice sorghum sugar beet Dose, kg / ha Southeast bush beans cotton bindweed turnip cassia tibora bloody weeds 3C 2C 0 0 0 0 0 0 2C, 0 0 2G 8H 5G 0 0 2C 0 IC 2C 0 3C, 3C,, 8G 4G - 8H 5H - 100 0.05 - 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 - - Compound .101 0.05 5C, 8G, 6Y9C 2C, IC, IC 0 ic, 2G 5G 4G 4G 9C ic , 2C, 4C, 3C, 3C, 4G 8H 9G 7G 7G 0 0 0 0 0 0 0 0 0 0 0 - 0 0 3H 0 0 0 0 0 0 0 0 0 - IC 0 0 0 0 0 0 0 IC, 2H 0 0 - 0 0 0 0 0 0 0 0 0 1H 0 0 -: formula 102 0.05 9C 9C 4C, 8H 9C 9C 10C 2C, 6G 103 0.05 4C, 7G, 6Y 1C IC IC 0 2G 043 142 885 44 one-sided deaf oats wheat corn soybean rice sorghum sugar beet Southeast bindweed cassia tibora bloody weed unilateral deaf oat wheat corn soybean rice sorghum beet 2C, 6H 0 and 0 IC, 4H 2C, 4H 2C, 4G 3C, 8H IC, 5G 0 - 3H 9G 2G IC IC IC, 5G IC, 5G 0 2G 3C, 5G sugar 2G Dose, kg / ha East bush beans tufted cotton bindweed turnip cassia tibora bloody weevil one-sided deaf oats cuckoo wheat ¬ soybean rice 104 0.05 - 9C 2C, 8G 3C, 6G 3C, 6G 5C. 9G 0 2C, 5G 2C, 9H 0 2G 1U, OH 9C 5C, 9H? C, 9H IC, 9G 2C, 8G nc 3C, 9G 3C, 9G 4C, 70 9G - 9G 10E 5G 5C, 9H 3C 8H 2C, 9H 8H 10E 19H 10E 105 0.05 9C 9C 5C "9G 9C 5C, 9G IC, 5G IC, 4G 3C, 9H IC, 3G 4G IC, 9G 9C 10C 5G 5G 2C, 9G 9C 9G 2C, 9G - 9G - 9G 10E 8G 9H 3C, 8G 8G 2C, 9G 7H 9H 5C, 9H - Compound 106 0.05 9C 4C, 8G 2C, 8H * C 5C ,, 9G 4C, 8G 4C, 9G 9C 2C, 9G 2C, 9G 10C 5C, 9G 0 0 0 0 3C, ic, ic, 4C, IC 0 IC 0 2G IC 0 0 8H 0? G IC 3H 4G 3G 9G: formula 0.05 9C 5C, 5C, 10C 9C 9C PC 9C 9C) C 10C 9C 107 9G 9G s 10 15 20 25 30 35 t 40 45 50 55 60 65 reams ^ ^ G sorghum IC ,, 9G sugar beet 2C, 9G Pre-emergence morning glory 9G turnip 9H cassia 8G chibora 9G bloody finger 2G weed - single-sided thread 3C deaf oats 2C, 4G wheat 6G corn IC, 9G soybeans 7H rice 10E sorghum 2C, 8H sugar beet 10E Dose, kg / ha Post-East bush bean cotton bindweed cassia tufa 5C, IC, 3C, 9G 9H 9G 8G 0 2C 2C, 6G 2U, 9H 10E 2C, 10E bloody finger 9G 9G 9G 7H 6G 9G 9H 5C, 9C 2C, 10C 9H 2C, 10 E IC 2C, 2C, ar * 5C, 2C, I0E 3C, 9G Compound c one-sided weed deaf oats wheat maize soybean rice sorghum sugar beet Post-eastern morning glory cassia tibora padusizniik blood weed weed unilateral deaf oats wheat corn soybean sugar 9G beet sorghum 8H beet 9G 9H 9H 9H 9H 8H 9H 9C 10C 9C GH 9H 9G 10E 8G 9H SC, 9G 10C 10H 9H 10E 6C, 9H 10E Formula 108 0.05 9C 5Q, 9C 4C, 5G 10C 4C, 8H 9C 5C, 9G 9C 9C 9C 10C 9C 9C 1QC 9C 8H 9H 9G 10E 8G 9H 5C, 9G 10H 5C, 9H 2C, 8H 10E 9H 10E 100 0.4 5C, 8G, 6Y 4C, 3H, 9G IC, 2H 5G 2C, 8H 9G 0 2C, 8H 0 0 2C. 6G 2C, 9G 6G 2C, 9H - 6G 8H 5G 2C, 8G IC 3C, 6H 2C, 6G 0 2C, 7G 2H 5G 2C, 5G —45 1 «* 5 46 Invention of JtiJ & poison following andEzyWadsy, the amounts of which are given in whole saga and temperatures in degrees Celsius, unless otherwise stated, examples for the preparation of the active ingredient are given for reference only. Example I. Preparation of 2,3-dihydro-2,2-meh (thyoyl-i74ene: 7-furianosafo chilo (r1) For a suspension of 32.6 g of 7-amino-2-y3-dihydro-2,2-dimethylbenzofuran and 4 (0% concentrated sulfuric acid in 200 ml of water, cooled to 0 to 5 ° C) , 13.8 g of sodium nitrite were added to give the diazonium salt After stirring for about 0.4 hours at 0 to 5 ° C, the diazonium salt suspension was poured in one portion into a mixture of 170 ml of acetic acid, 40 ml of concentrated hydrochloric acid, 17 g of cupric chloride dihydrate and 30 ml of sulfur dioxide, and the temperature is kept at about 10 ° C and cooled in ice water. Stirring for approximately 1 hour at 15 to 25 ° C. Then 400 ml of 1-oMorobutane and 200 µl of water were added and the reaction mixture was stirred and heated at 3-5 ° C for 5 hours. After cooling to room temperature, the organic phase was separated, washed with a saturated aqueous solution of NaHCO 3 and water and dried over sodium sulfate for 0.5 hours. The solvent was evaporated under reduced pressure at a temperature below 45 ° C to obtain 26 g of crude 2,3-dihydro-2,2-dimiethyl-7-benzofuiranesulfochoride as an oil. Example II. Preparation of 2,3-dihymethyl-7-benzofuranosulfionamide. A solution of 26 g of 2, 13H-dihydro-2,2-dimethyl-74) enzofuranesiiifchloride obtained in example 1, in 130 ml of tetrahydrofuran, cooled in water with loid, and 30 ml of concentrated aqueous ammonium hydroxide solution, maintaining a temperature of 10 to 30 ° C. The resulting suspension was stirred at room temperature for 3 hours, and then the solvent was evaporated under reduced pressure. The residue was stirred in 150 ml of water for 0.5 hours and then filtered. The durum wet solids were dissolved in chloroform and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give a dry solid. These materials were washed once with about 100 mL of hot toluene to give 20 g of 2,3-dihydro-2,2H-dimethyl-7H-benzofuranisifonamide, m.p. 163-165 ° C. 1 4 Elemental analysis: calcd for C 10 H 14 NO 3 S: C 52.8 H 5.8 N 6.2 Found: C 52.5 H 5.7 N 6.1 Example III. Preparation of N- / butylamino-carbonyl / H2,3-dihydro ^^ - diimethythet-7-tbenzlofuran-sulfonamide ~ r 'Solution 19 g 2,3-dihydro-2,2-cH-methyl-7-benzofuranesulfonamide obtained in the example II and 9.9 g of n-t-butyl isocyanate in 200 ml of 2-butanone were heated for 7 hours under reflux with 11.5 g of anhydrous potassium carbonate. The resulting reaction mixture was evaporated to dryness under 100% pressure. The residue is taken up in 400 ml of water and effected once with 100 ml of diethyl ether. The aqueous water was decanted with N HCl and the yellowish mixture was drained and pre-dried on the left side. The still slightly moist solid suffostants were washed once with 100 miles of hot acetonitrile, air dried in a funnel under a flow of air and then dried. 10 steps were taken for 8 hours under reduced pressure, yielding 23 g of N-utylaminocarbonyl (^^ - diihydro ^^ - ^ diimeth ^ yl-T-ibenzofuranos ^ fonamide with a melting point of 200 ° F2013 ° C. Elemental analysis: calculated for C15H22 (N264S: C 55.2 H 6.8 N 8.6 Found: C54.8 H 6.6 N 8 * 5, Example IV. Calibration N - [/ 4.6 2.5 g of the 2,3-Hihydiro-isocyanate prepared above was added to a solution of 1.2 g of 2-amino-4,6H-dimethylpyrimyl- dine in 25 ml of tetrahydrofuran. -2,2-dimethyl-7-benzofuransulfionyl. After the temperature rose slightly as a result of the extermic reaction, the solution was stirred under room temperature for 4 hours. the formation was narrowed under reduced pressure to obtain a viscous oil, from which a solid precipitate was precipitated out of 10 ml of acetonitrile. The precipitate is recrystallized from acetonitrile, containing 2 g of N -, [4,6-methylpyrimidinyl-2H-amino carbonyl] -2-, 3-ihydro, 2-diimethyl-7-benzonimide, melting point 20 ° C. - 206 ° C. Widimo IR showed absorption by the carbonyl group at 1680 cm3 indicating a sulfonylurea. Elemental analysis: calculated for CnU ^^ OS: C 54 ^ 2 H 5.4 N 14.9 Found: C '54, 3 H 5.4. N 15.2 Example DIAM. Preparation of 7-Amino-2,3-dihydro-methylbenzo [b) tdophene 80 g of sulphide (2-aninophenyl) allylt was heated for 3 hours at 25.0 ° -28 ° C, oohl. - the dizono and then subjected to spinning film distillation through a 20 cm column using a 5: 1 diaphlegmation rate. 18.0 g of a fraction distilling in the range 80-82 ° C at 33 Pa was collected; WDdima NMR analysis showed that it is a tyhilic compound with a purity approximately GWo. Results of NMR spectrum analysis (ODCU) 5: 7.0- ^ 6.3 (m, 3H, ArH), 3.9 (m, 1H, Cfi ), 3.5 (broad, 2H, 50 NH2), 3: t5M2.6 (m, 2H, CH3), and. 1.35 (d, 3H, CH "), Example VI. Preparation of 7-acetamido-2,3-dithydro-2H-methylbenzo [bifthiophene, For a solution of 18.0 g of 7-aminoH2-3-dihydro-2-methylbenzo [ib] thiophene from example V in 100 ml of 1-chloro To 55 robuitan, a solution of 13.0 rM acetic anhydride in 20 ml of 1Hchlorobutane was added. After the exothermic reaction was completed, the mixture was heated to; - reflux for 0.3 hours, cooled in ice-water and filtered. The isolated solid was washed with 1-chlorobutane to give 15.2 g of the title compound, mp 125 ° C. <127tC Results of NMR spectrum analysis (ODOI3) 8: 7.8-6.7 (m, 4H, ArH + NH) / 40 (m, 1H, CH), 3.6-2.8 (m, W 2H, CHj), 2.2 (s; 3H, CH3), and 1.4 (d, 3H, CH8K142 885 47 48 Example VII. Preparation of l, r-dioxide 7- * ^ IftcefoaiinikJo ^ For a solution of 24.7 g of T- acfeitimido-α-hydro-phytometh-Wobenzto (ib] thiioiphene from Example 6 in IDO ml of glacial acetic acid, 60 ml of SOf / l of aqueous hydrogen peroxide solution were added dropwise. During the addition the reaction temperature rose to 65 ° C. The mixture was heated for 1 hour at 65-75 ° C., cooled to 25 ° C., diluted with water and extracted with methylene chloride. The extract was washed with water saturated with sodium phosphate, dried over magnesium sulfate and concentrated under Ammiejiszonfm under pressure The oily residue of the crystalline and ammonium chloride of chloirobuitane, yielding 14.3 g of the title compound in the form of light yellow crystals with a melting point of 115-117 ° C. The results of the NMR spectrum study (CDd3) S: 8.4-7 [mu] O (m, 4M, ArH + NU), 38- ^ 2.7 (m, 3 H, CH 2 + CH), 2.2 "," 3H, CH 3), and 1.5 (d, 3H, CH *). Example VTCI. Preparation of 1-, yl-dioxide 2,3-hydro-E-imethyl-7-benzo. Solution of 18.6 g of 1,1'-acephta 1,1'-dioxide (midio-2,3-ihydro-i2Hme (butbeni & ofb) The thiolfene from Example 7 in 100 ml of concentrated hydrochloric acid was heated under reflux for 1 hour to give a suspension containing 1,1-dioxide 7-aimi-2y3Hdihydihydrochloride. The suspension was diluted to 25 ml of ice. - waftegic of acetic acid, cooled to -5 ° C, and treated with a solution of 6.4 g of sodium nitrite in 10 ml of water so that the temperature did not rise above 5 ° C. The reaction mixture was stirred for 0.5 hours at 0 ° C, and then added in one portion to a cooled to -7 ° C suspension containing 50 ml of concentrated hydrochloric acid, 50 ml of glacial acetic acid, 2.0 g of cupric chloride dihydrate and 10 ml of condensed sulfur dioxide The reafccinin mixture was stirred for 2 hours at 20 ° C, then diluted with water to cause precipitation. The reaction nine was drained and the solid residue washed with water to give crude 1.1M 2-methyl-α, 3-dihydro-7H-benzo-I ^ ^ ^ ^ ^ ^ ^ ^ ^! solid product. This solid product was dissolved in methylene chloride and contact with 7 ml of liquid ammonia at a temperature of -10 ° C. The reaction mixture was stirred for 16 hours at 2 ° C, after which it was filtered off and the solid residue was washed with water and ether. The wet solid residue was suspended in benzene and refluxed with a Deam-Stark adapter until Water is not distilled from the slurry. The slurry was cooled and drained, yielding 11.4 amps of the title compound with a melting point, W1 — WMPC. NMR spectrum test results (CDC & 3 + DMSO) S: 8.1— 7.5 (m, 3H, Ar), 74 (broad, 2H, NH2), 3.8-2.5 (0% 3H, CHa + CH) and 1.5 (dv 3H, CHs). in infrared (nujoi): 3360, 32100 camr1 (NTL). Example IX Preparation of 14th dioxide N- ^ / 4HmoWk! sy-6H-methylprimidinyl] -2.3Hdifihydro-2Hmethyl-7-benzio [bphthiophenosLphonide 1.15-suspension g of 2,3-hydroxide 2,3-dihydro-2-methyl-7-benzo [bithiophenesulfonamide from Example 5 on VIII in 20 ml of dry methylene chloride was purged with nitrogen. 3.0 ml of a 20% toluene solution was carefully diode to the suspension. oru trimethylaluminum (Aldrich Chemicals) while cooling the flask to maintain the temperature in the range 10 to 30 ° C. After stirring for 0.2 hours, 0.9 g of methyl (4-t-methoxy-6-methylpyrimidinyl-2-hydroxymethyl) was added in one portion and the resulting slurries were refluxed under nitrogen for 24 hours. The suspension is cooled in ice water and 20 ml of kN hydrochloric acid are slowly added After stirring for a few minutes, the organic layer is separated, washed with water, then water saturated with sodium chloride (brine), dried over magnesium sulfate and concentrated. - under reduced pressure. The residue was triturated with chloroform and methylene chloride to give 0.3 g of the title compound with an attenuation temperature of 224-226 ° C. 25 Results of NMR spectra (CDCl.sub.3 + DMSO) 8:10 , 3 (broad, 1H, NH), 8.2-7.6 (m, 3H, Ar), s, 1H, CH). 4.0 (s, 3H, OOHs), 3.7 ^ 2.8 (im, 3H, CH + CH), 2.5 (s, 3H, CHB), and 1.5 (d, 3H, CH3) . Results of the infrared spectrum test (nujol): 1700 cm-1 30 (C = C). Preparation of N-II-Tert.H-butyl-2- (2-methyl-2-propenylthio) | benzenesulfonamide in an ice-cooled solution of 42.6 g of N-IIi-butyl-benzenesinamide in 800 ml of dry tetrahydrofuran under nitrogen, 262 ml of a 1.6 M solution of n-butyl lithium in hexane were added dropwise. The reaction mixture was stirred for 2 hours at 20 ° C during this period a precipitate formed. The slurry was cooled to 40 ° C. to 0 ° C. and cooled to as much as 6.4 g of elemental sulfur in one portion. The mixture was warmed to 20 ° C. and stirred for. 1 hour, then cooled to 0 ° C, slowly adding 20.5 ml of metaalyl chloride. The reaction mixture was stirred for 16 hours at 20 ° C, and then 100 ml of a 10% hydrochloric acid solution were added. After stirring for a few minutes, the organic layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was suspended for a few minutes in a 20% mixture of ether in hexane and filtered off to give 47 g of the title compound, m.p. 104-107PC. Specifications for NMR spectra (CDCl3) 5: 8.2-7.2 W (m 4H, Ar), 5.6 (broad, 1H, NH), 4.9 (broad, '2H, vinyl group), 3.7 (s, 2H, CHa), 1.9 (m, 3H CH3), orafe 1.2 (p <, 9H, Illifiz.-butyl). Example XI. - Preparation of N-IHrzHbutyl -®, 3-dilhydro-2,2-dimethyl-7-benzo [b] thiofeinosiphon-60amide - - Solution of 37 g of N-HIrz.-1butylOH2- / 2H-methyl-B-propanylortial ^ The beintzenesulfonamiid from the example 'X in 40 ml of Mnottima was heated for 1 hour at 220 ° C, then cooled to 25 ° C and diluted with ether. The ether suspension was washed with 16SS 50 exactly 10% hydrochloric acid, then water and brine, then dried over magnesium sulphate and concentrated under reduced pressure. The oily residue of chiroanait was graphed onto 300 g of silica gel, loaded onto the column and eluted. a 20% solution of ether in hexane to give the main fraction which was concentrated under reduced pressure to give a solid. This product was suspended in a mixture of 20% ether in hexane and filtered to give 14.2 g of the title compound, m.p. <5I3: -I105 ° C. Results of wiicfcma NMR (GDO1j) 5: 7.9-7.0 (m, 3H, Ar), 5.0 (broad, In; NH, 5 3.115 (s, 2H, OH3 ; R3, R4, R'4, Ri, R are hydrogen; W oafytyl). Infrared spectrum test results (nu-mol): 3200 cm-1 (NH). Example XII. Preparation of 2j3-dlihydro-2, 2--tdfimety ^ o-74en2K [to] thiofenosii (llonam) idu A solution of 17.2 g of N-III-butyyl ^^ HdlhydiroHZ ^ J-dimethyl-7-ibenzorb] thioifenesulfonaimidti from example XI in 100 ml of triHoioroacetic acid was stirred for 16 hours at 20 ° C. The solution is concentrated under reduced pressure, 100 ml of fresh triifluoroacetic acid are added and the whole is stirred for another 4 hours at 20 ° C. After concentrating the solution under reduced pressure, the residue is dissolved in methylene chloride and the solution is washed with saturated aqueous sodium hydrogen carbonate solution followed by brine, dried over magnesium sulfate and concentrated in vacuo. The solid residue was suspended for a few minutes in a 5CP% ether mixture. in hexane, and then desalted to give 8.4 g of the title compound with a melting point of 102-104 ° C. Results of NMR spectrum analysis (CDC13) at: 8.0-7.0 Cm, 3H, Ar) , 5.1 (broad, 2H, NH2), 3.2 (s, 2H, CH2), 1.6 (s, 6H, CH31). Infrared spectrum test results (Nuijol): 3300 cm-1 (NH). Example Xliii. Preparation of 1,1-dioxide 7-nitrobenzo [to] thiophene To a solution of 24.8 g of 7 Nitrobenzo [to] lthiophene in 200 ml of glacial acetic acid, preheated to 100 ° C, 90 ml of 30% aqueous peroxide solution was added hydrogen at a rate such that the temperature remains in the range of 100 to 105 ° C. The solution was heated under reflux for 1 hour, then 200 ml of water was added and the mixture cooled in an ice-water bath and drained. The solid residue was washed successively with water; ethanol and ether, yielding 20 g of the title compound with a melting point of 195-197 ° C. Results of the ttMR spectrum (CDd3 + DMSO): 8 £ (m, 1H, Ar), 8.0 (m, 2H, Ar), 7.6 (m, 1H, Ar), and 7.2 (m, 1E, Ar). The research results. wildima in rediscoloration (nujoi): 1540 and 13i0Ó om-1. Example XIV. Preparation of 7-amino-2,3H-dihydrobein-14-dioxide [ib] thiophene 19 g. 1,1H-7-n-troibenzo [ib) thioiphene dioxide of Example XIII was hydrogenated in 200 ml of ethyl acetate over 1.0 g of a catalyst containing 10% Pallet on charcoal, under a pressure of 3.45 nSFa and at a temperature of 10 ° C until no more gaseous hydrogen is absorbed. The mixture was drained through celate and the meshed was sealed under reduced pressure. The solid residue was recrystallized from 11 chlorobutaffia to give 13J2 g of the title compound, mp 117-419 ° C. vrf Wytniflri studies of NMR spectra (CDCtb + OMSO 8: 7; 3-6.7 (m, 3H, Ar), 5.1 (broad, 2H, NHi), and 3.4 (m, 4H, CHa). Results infrared spectrum studies (nujol): 3400, 3300, 1630 and 1 * 590 tm ~ K Example XV. Production of 1.1 ^ 2,3 ^ dihydax) -74) eniso (lb] thiophenesulJforiaimide for a suspension containing 12 , 8 g of 7-a, mino-2,3-fthydiroibenzo-dioxide, lib] thiophene from Example 15 XIV, 25 ml of glacial acetic acid and 76 of concentrated hydrochloric acid, cooled to a temperature of about 6 ° C and 5 ° C to 5 ° C to the hit reaction mixture, a solution of 5.3 g of sodium nitrite in 10 ml of water was added to give the diazonium salt. After stirring for 0-5 hours at 0 ° C, the suspension of the diazonium salt was added dropwise to a mixture of 75 ml of concentrated product. hydrochloric acid, 50 ml of glacial acetic acid, 1.0 g of mftecMowegp 1 chloride diphydisylate, 8.0 ml of condensed sulfur dioxide, decorated during the addition to -5 ° C. The reaction mixture was stirred for 1 hour at the temperature of the 0 ° C and heat for 2 hours at 20 ° C, then rot. thinned with excess water and stirred until a precipitate was formed. The reaction mixture was filtered off and the residual solid was washed with water to give crude 1,11,2 2,3-dihydro-7-benzo [ib] thiophen sulfchloride dioxide. The sulfo-chloride obtained above was dissolved in methylene chloride and dried over magnesium sulfate. The dried solution was contacted with 5 µl of condensed ammonia at -T ° C and then stirred for 18 hours at 20 ° C. The suspension was concentrated under reduced pressure and the residue was suspended in 10 µmL of 10 Vt hydrochloric acid and then filtered off. The solid residue was washed with water and ether to give 11.5 g of the title compound, mp 215-217 ° C. '* 45 NMR spectrum analysis results (CDOb + IfcMSO) δt 84-7.6 (m, 3H, Ar), 7.0 (broad, 2H, tfH *) and 3.8-3.3 (m, 4H, CH2). The results of the examination of infrared spectra (nujol): 313 100, 3200 and 1350 cm-1. Example XVI. Production of l ^ l ^ dioxide 50 N - [/ 4Hmethoxy ^^ ethylphthylol ^^^ dihyck ^^ benzofblthiophene Suspension 1.0 g of 1,1-2,3 ^ iihydro-7-toett- ~ zo [b) thiofenesulllbnamid of Example 15, in 20 µl of dry methylene chloride, 2.5 ml of a 55% toluene sulphonic solution of TrimethUogltou- (Aldrich Cheimicals) was treated under a blanket of dry nitrogen. After stirring for 0.215 hours at a temperature of 20 ° G, 1.0 g of methyl 4-methoxy-6-imethyteti-pyrimidinyl) was added in one portion and the resulting solution was stirred for 60 hours at W20 ° C, and then, for 24 hours, the mixture was heated at the "reflux temperature. Mtt ^ C; the shanine was cooled in a bath of water with UodemjT, and then treated with 10 ml of iOf / o adk ;, and drained. The remaining residue was heated to this" 142 685 51 tranydrofuran and drained hot to give 0.45 g of the title compound with a melting point of 227-220 ° C. Results of the NMR spectrum study (CDGU + DMSO) 6: 13.7 (broad, 1H, NH), 10.1 (broad, 1H, NH), 8.2-7.7 (m, 3H, Air), 6.3 (s, 1H, CH), 4.0 (s, 3H "OCH3), 3, 5 (im, 4H, CH *) and 2.4 (s, 3H, CHa). The results of the spectral examination in the reddish void (nujol): 32O0 (NH), 1710 (C = G) cm-1. Using the techniques described in in the schemes 1 ^ 23 and the above examples, or their minor modifications, "the compounds listed in the table are obtained III, IV and the following compounds: the compound of formula 48, where Ra, R3 and Xi are CHa, R4, R'4, Ri, R are hydrogen, W, Qi, G are oxygen, mp 207-208 ° C; Compound 48, wherein R2 and Xi are CH3; Ra, R4, R'4 ,. Ri and R are hydrogen, W and G are oxygen and Qi is SO2I, mp 208-2110 ° C; a compound of Formula 49, wherein R2 and X2 are CH3; Ra, R4, R%, Ri, R are hydrogen, W is oxygen, Qi is SQ2 and Y2 is OCH3, mp 204-206 ° C; a compound of formula 50, where R, Ri, R2, R3, R4 are hydrogen, W and Qi are oxygen, X and Y are OCH3 and Z is CH, mp 177 ^ 180 ° C. R2 1 CH3 CH3 CH3 OH3 CH3 CH3 Chh CH3 CH8 CH3 CH3 HHHHHH CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH, R3 ~~ 2 ~ HHHH CH3 CH3 CH3 CH3 CH3 CH3 CH3 HHHHHH CH3 HHHHHH3 CH3 HHHH hhhhhh CH3 CH3 CH3 CH3 CH3 CH3 R4 _ 3 "HHHHHHHHHHHHHH II HHHHHHHHHHHHHHHHHHHHH HHR 4 ~~ 4 ~~ HHHHHHHHHHHHHHHHHHHHH HHHHHHHHHHHHHHHHH R five HHHHHHHHHHHHHHHHHHHHH HHHHHHHHHHHHHHHHH Table 6 R ~~ HHHHHHHHHHHHHHHHH CH HHHHHHHHHHHHHHHHHHHH ica III; ~ 7 OOOOOOO 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 v 0 0 0 0 0 0 Qi ~~ 8 ~~ OOOO 0 0 0 0 O '0 0 0 0 0 0 0 0 0 sssssss 6 S02 so2 SOa SO2 so2 so2 SOo so2 SOa SOo so2 so2 X ~~ 9 ~ OCH3 OCH3 CHs Cl OCH 3 OCH3 CH3 OCH3 OCH3 CH3 Cl OCH3 CH3 CH3 OCH3 OCH3 Cl OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OOH3 OCH3 OOH3 CH3 CH3 OCH3 OCH3 Cl oce3 OOH3 CH3 OCH3 CH3 CH3 CH3 OCH3 CH3 OCH3 CH3 CH3 CH3 OCH3 OCH3. OCH3 OCH3 CH3 OCH3 CHs OCH3 OCH3 OCH3 CH3 OCH3 CH3 OCH3 CH3 OCH3 CH3 OCH3 OCHa CH3 OCH3 CH3 OCH3 OCH3 CH3 CH3 OCH3 OCHs CH3 Z 11 CH CH CH CH CH CH CH NNN CH CH CH NN CH N CH NN CH N CH NN CH N CH CH CH NN CH CH CH CH NNN melting point i ° C) 12 182- 186 195-198 178-182 175-480 198-400 170- ^ 172 203- ^ 206 164 ^ 168 162-il65 172 - ^ 176 165- ^ 167 211- ^ 215 207—212 200—004 (decomposition) 192—196 180 —jl8 / 5 201-H205 151—152 177 ^ 179 220—223 167-H169 .145—147 190—192 2110—012 146 ^ 140 183—185 234-H236 238—240 214—226 160 ^ 170 214—216 223—226 236—238 228—229 228—230 214-H216 205—007 208—21 153 142 685 54 T CH3 C2H5 C2H5 C2H5 HHH .HHHHHHHH CH3 CH3 CH3 CH3 CH8 CH3 CH3 HHHHHHHHHHHHHHHHH or 6- J 4'1 5- or 6- J 4 "1 5- or 6- J 2 CH3 HHHHHHHHHHHHHHHH CHs H H: HHH iRi ~ T— ia 1 1 a 1 a 3 HHHHHHHHH CH3 CH3 CH3 CH3 CH3 HHHHHHH CH3 - (Rio 2_ CH3 CH3 CH3 CH3 CH3 HH CH3 HH OH3 CH3 CH3 CH3. CH3 HHH 4 CHHHHHH3 HHHHHH3 HHHHHH3 (HHH RHH) ~ HHHHH CH * CH3 HHH CfH3 CH3 CH3 CH3 CH3 CH3 OH3 CH3 5 HHHHHHHHHHHHHH ¦HHHHHH CM3 - HH - R ~ ± ~ HHHHHHHHHHHHHHHHHHH 6 iH HHHHH. H 'HHHHHHHH CH3 CHg CH3 HHHHH Ta r W 5 ~ OOOOOOOOOOOOOOOOOO 7 OOOOOOOOOOOOOOOOOOOOOOO OO blica IV formula 511 Q 6 OOOOOSSO tss so2 so2 so2 so2 so2 sss 8 SOj S02 S02 S02 S02 SO2 S02 SO2 SO2 SO2 SO2 SO2 SO2 SO2 SO2 SO2 so2 so2 SOa X 7 ~~ OCHs OCH3 CH3 OCH3 OCH3 OCHg CHg OCHs OCH3 OCH3 OCH3 CHs OCH3 CH3 CHa CHg OCHs 9 Cl OCHa OCH3 OCH3 OCH3 CH3 CH3 OCH3 OCH3 Cl OCH3 OCH3 CH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 OCH3 ~~ OCHg CH3 CH3 OCH3 CH3 OCH3 CH3 CH3 OCH3 CH3 OCH3 CH3 CH3 OCH3 CH3 CH3 OCH3 OCH3 10 OCH3 OCH3 CH3 CH3 OCH3 OCH3 CH3 OCH3 CH3 OCH3 OCH3 CH3 CH8 OCH3 CH3 OCH3 OCH3 OCH3 OCH3 CH3 OCH3 OCH3 11 OCH3 OCH3 NN CH CH CH CH NN CH NN CH CH CH CfH / OCH ^ CH CH3 Z 9 ~~ CH CH CH NN CH CH N CH CH CH CH CH CH NN CH CH CH N 12 226—208 221 ^ -023 215—217 180 —Aa2 3O0 227-H220 28Ó — 032 208—2) 10 210—013 229 ^ 314 V2B! 2 ^ 235 221 ^ 223 199 ^ 208 200-H204 211 ^ 213 208 ^ -011 160—163 182—484 225—226 233 ^ 234 218-020 111-113 203-006 there melting peiraitufra, ° C 10 188-191 208-211 19 8-420 (2 172-176 178 ^ 181 1216 ^ 218 218 ^ 220 201-004 204-H206 195 ^ 197 236 ^ 239 237—2319 249 ^ 252 026-230 203-236 218 220 220 2131-233 and 218 21 21 21 Example XVII. Suspension brooch 60 syotephthalic amorphous silica 3 * / o 14-dioxide NH [/ 4; 6, 6-dimethyl-pyrinidinyl-cadidite 13% -aliminoc-2-methyl-7]. The ingredients are mixed and grinds 801% of the miotco-benzathiophenosphonaimide in a mill until the average particle size of sodium alkynaphthalenesilonium 2% is obtained, below 50%, and then it is mixed again with sodium pylagminosuliponate 2 # / about 65 kuqe.14l68 »55 56 Example XVIII. Alley suspension N - (4H-meitoxy-mephthiopyrin-dy4iyioH2 and t3-dioxide) <^ 7Hb «nzoft! Ioife (nasal Iifonaimide 25% aatescioolateate polyoxyethylene sulfolite ^ u 5% 5 o icfi & e and content of aliphatic hydrocarbons /; - 70%". The gesite suspension can be used directly, but it is preferably used after dilution with oils or emulsification in a fleece. Example XIX.N | Wettable powder 14.2 NH [4,6-dimethoxy-pyrimidinyl] ! inocarbonyl ^^ l * in benzene <) 4to ^ eno (sullfonamiridw 20% afflkiionattalenosilphonate sodium 4% lifeninosulfoniansodu 4% me $ icellulose - low viscosity 3% aittajpulgite 69% w The ingredients are carefully mixed. After grinding in a hammer mill until a particle size of 100 | is obtained. / the material is remixed and sieved through a USS sieve No. 50 (0.8 mm openings) and packed. 25 ° C cycle XX. Low percentage granules 1,1-N dwut-dioxide / 4,6-dimethyl-1,3,5 -tarazinyl-phyl ^ -aminocarbonyl] -Q, 3-dihydro-2-methylHo-7- n-benzothiophenesulfonamide 0, (1% ^ aittapuiLgate granules 99.9% 30 {20-40 mesh sieve) ^ Active substances dissolves in a solvent and the solution is sprayed onto the dust / granules in a twin-cone mixer. After spraying of the solution is complete, the material is heated until the solvent evaporates, after which the material is allowed to cool and then packaged. Example XXI. M, N - ((4H-methoxy-6H-methylol, 1,3v5-40) Maiazinyl) - aminocarbonyl] -2,3-thanydrine-2-thimidide Ethyl-T-lbenzo-ifuranesulfonate 80% wetting peas 1% crude iignihosulfonate (containing 5- & 0% natural sugars 10% 4 * adrtaputtlgite clay "¦ 9% The ingredients are mixed and ground so that they pass through a 100 mesh screen. This material is then "fed into the granulator operating in the fluidized bed, the air flow is adjusted so as to gently fluidize the material and a gentle spray of water is directed onto the lumpy material. Fluidization and spraying are continued until granules are formed. The spraying is then switched off and the fluidization continues, possibly with the addition of heat, until the water content is reduced to the desired level, usually below 1%. The material then discharges, passes to the desired level. particle size range, 60 / Wytele 14- (1O0 mesh (1410- <140 nm) and packed for use. ^ ¦¦ \ Example XXII. Concentrate of high-percentage and # * N - {(4,6-dimethoxy-1,3,5H-triazine- [5-nyl-2] -airninocarbonyl] -2.3% -l-7-lbenzo (thiolenesulfonamide 09% aerosol) concentrate silica 0.5% synthetic amorphous silica 0.5% The ingredients are mixed and ground in a hammer mill until the material is obtained, which essentially passes through a sieve with 0.3 mm holes. This concentrate can then be used for preparation further formulations as required. Claims 1. A herbicide for controlling the growth of undesirable vegetation and regulating plant growth, comprising an active ingredient and at least one of a surfactant and a solid or liquid diluent, characterized as the active ingredient contains a compound of formula I, in which J is a group of formula 39, 40 or 41, and Q is oxygen, sulfur or SO2, Q1 is oxygen, sulfur, SO or SO2, R is a hydrogen atom or a methyl group, R and is a hydrogen atom, a methoxy group, a methoxy group, a chlorine atom, a bromine atom, - the group NOa, CO2R8, SO2R6, OSO2R7 or. SOs1NRsRj1, Ra is a hydrogen atom or an alkyl group of 1-3 carbon atoms, R3 is a hydrogen atom or a methyl group, R4 is a hydrogen atom or a methyl group, R'4 is a hydrogen atom, a cMorium atom, a methyl group, a trifluoromethyl group, methoxyyl or atfpm, R5 is an alkyl group of 1-3 carbon atoms, CHtfCH = CH2, CH2CH3OCH3 or GH2OH4Cl, R6 is an alkyl group of 1-3 carbon atoms, R7 is an alkyl group of 1-3 carbon atoms or the trifluoromethyl group, Rs and R9 are independently of each other an alkyl group with 1-2 carbon atoms, Rio is a hydrogen, chlorine, bromine atom or an alkyl group with 1-3 carbon atoms, Rn is a hydrogen atom, a methyl group, a chlorine or bromine atom, W is oxygen or sulfur and A is a group of 42, 43, 44. 45 or 46, C is oxygen atom or CH2 group, X is hydrogen atom, methyl group, methoxy group or chlorine atom, Xi is methyl group, methoxy or ethoxyyl group, X2 is methyl, ethyl or CH2CF3 group * Y is methyl group , methoxy, ethoxy, CH2OCH3, NH2, NHCH2N / CHa'2, CH / OCH3 / 2, group of formula 47, ethyl, trifluorhethyl, CH2 = CHCH2O, SCH3, HC == CCHaO or CFsCIfeO, Y stands for ethyl, methyl, methoxy, epoxy, SCH3 or SCjHs, and Z stands for CH, nitrogen, OCH3, CO2H5, OQ or ORr, and their agriculturally acceptable salts, with the restriction that (1 ) in the groups of formulas 39 and 40, when Qi is oxygen and Ri is a substituent other than hydrogen, chlorine, bromo or NO *, then at least one of R2 and R3 is an alkyl group, and when Qi is an atom <* iairkl, then R 1 cannot be NO 2, (2) in the group of formula 41, when R 1 is NO 2 or SO 2 NR 6 R 7, then R 0 is an alkyl group with 1 to 3 carbon atoms, and Ru is a methyl group, (3) when X is a chlorine atom, then Z is a CH group, and Y is a meithoxyl group, NH2, NHCH3, N / OHWi, (4) when Qi is a SO group, then W is an oxygen atom, and (5) when R'4 is a substituent other than a hydrogen atom, Ri is a hydrogen atom. 2. Measure according to yzasitrz. 2. A process as claimed in claim 1, characterized in that the active ingredient is N-C / 4.6% neltyaicin, dihydro-2-methyl-7-benzenethiolenesulfionamide. 3. The measure according to claim 2. A process as claimed in claim 1, characterized in that the active ingredient is 1.1 ^ N- (4Nmeltxtoy ^ Hniety ^ ^ ^ methyl] ^ ^ 3HO ^ droH2Hme ^ yl ^ 7 ^ benzenethiophene sulfonamide. 4. The agent according to claim 1, characterized in that the active substance is N-4 / 4.6 ^ imeftoxyparine-tidinyl-2 ^ ^^^ hydro (only 6-74) enizene (thiophenesulfonamide). according to claim 1, characterized in that the active ingredient is 1,1-dioxide N-4/4 ^ H-dimieitylOH1, 3 ^ H2.3 ^ hydro ^ Hmethylp ^ Hbenizo ^ O (phen 6. The agent according to claim 1, characterized by the fact that it contains as active substance 1, 1, n-methoxy, H -methyl-3, 3, i5-itria ^ bonyflo] -2.3 Hdfinyide! TO ^ methyl-74) ^ ^ 5 amide. according to claim 1, characterized in that the active substance is N-H [M, 6-dimethi] [M, 6-dimeth [M, 6-dime {toc6yHl, 3, 5, tm-2, 13-iinydin] -neityl-7Hbe ^ 10. A compound according to claim 1, characterized in that the active substance is 2,3H-dlihydroOHN - [/ 4-N-meitoxy-6-methylpyrimite-2-H-meitylbenzofuran-7-sulfonaimide. 9. An agent according to claim 1, characterized in that the active substance is Ni [/ 4,6-diimeltoxy-pyrimidinylH2 / anunocarbonyl] H2,3-dihydroH2-imethylbenizo furanoJ7nsulflonaniid. 10. The measure according to claim A compound as claimed in claim 1, characterized in that the active ingredient is N-4 / 4v6-Hdilrne4xfc n2,3-idihydlroibenzio [to] itiotphene, 7Hsullifonaniidii 11. The agent according to the present invention. 2. A compound as claimed in claim 1, characterized in that the active substance is 2,3- ihydro-4-hydroxide [i4-methoxy-methylpyrimidinyl-2 / - 25 aniinocaribonyio] ibenzo [ibJthioiphene-7HSuIphonamidf. 142 685 W II JSO NHCNA R Ry PATTERN ^ 3 O II SO9NHCN 'LI Cl NHR, PATTERN 26 R1HN- ^ n-SO-NHR2 H3C- PATTERN 29 R1 PATTERN 27 PATTERN 30 OCH: r, / 7 = \ II N - ^ CH ^ - S0oNH- C-NH ^ P) NWN ^ OCH 3 X H2N - ^ QZ FOR MODEL 3 a CH, FORMULA 28 Xl N H2N ^ nO O MODEL 3 d FORMULA 31 WR ^ SO ^ NH-C- NH-R MODEL 32 X • W MODEL 3b Xi X H- (H2N ^ Q NA Y MODEL 33 X N_y ^ Qn nK with MODEL 3c MODEL 3e MODEL 34142 685 R3 R, R7 R5 MODEL 35 R8-Q 'R / R' R RR: MODEL 39 Ri R , R2 Ql R3 XO / Z¬ NA Y PATTERN 42 Xl naJ PATTERN 36 R9 "PATTERN 37 PATTERN 38 Ri PATTERN 40 .R, 3 ^ —R, PATTERN 41 PATTERN 43 XL PATTERN 44 R * V ^ iwx li - / ¦SCLNHCN - (Qz RN ^ R4 R1 Y X1 R3 R2 0 CH3 (Oz-SChNHCN-e I ^ = YIM * \ R * R, X- MODEL 47 R4 R3 R2 MODEL 45 * 2 R ¦ Y2 MODEL 49 \ Q] wx, W II N ^ O-SO2NHCN <.RJ R, KG 4 1 MODEL 48 / MODEL R2, R3 QfVR4 W / 2H II WO ^ S02NHCN ^ Q / W 'Ni.Rt R MODEL 50 YL9 ypZM 89 dOZM £ H0V 20S ^ VN 7 M NO) - HN - 3 - HN - 0S ~ (O) T ^ N II ^ £ H00 O 09 dOZM -HO, NW O-HN-3-HN-OS ^ O) 'HOO °. 6S dOZM £ H3 Z0S "^) (OyH N- 3- HN- OS- (Q. / Hd II ^ 'H30 O SS dOZM £ H0 £ H0 -HO O * .J)) ^ HN-0-HN-20S - (O c / NO 'H30 ys aoz / v \ £ H0 N £ HO £ HO' O '(OHN ^ HN- ° s-CJ N' HOO O £ S doOZM 'HOO HO HO o: yn. _ X 'HOO O ° HO C) ^ HN-3-HN-3OS ^ O e / N 1! - bHO O ZS dOZM' HO VN NO ^ HN- 0-HN-30S- (O / 'HO ^ O 9S yoz / v \ 'HOO ¦ £ HO £ HO O NO) - HN-0- HN-30S-O ^ N || XW / £ HOO • O 35 dC ^ £ H3 £ HO £ H3 O' OVHN-0-hN-20SyQ £ HO ° zD / - ^ HNZOS ^ QX. W La Oi d 689 Z? I142 685 OCH./F* \ II N ~ (O ~ S0 -NH-C-NH-XO / N (SO9 N \ V / ^ J2 CH3 FORMULA 62 0 * CH-, <0-so2-nh-c-nh4q yso2 N \ CH: FORMULA 63 0 CH3 O-S0-NH-C-NH ^ Q Cso2 'n and CH- 0CH3 FORMULA 64 0 OCH3 r ~ \ II N ^ QVS0 -NH- C-NH-O rnf NA \ ^ SO? OCH: CH- FORMULA 65 0 OCH3 -S00- NH - C -NH- (O / N, SO. CH 3 CH- FORMULA 66 9 OCH. (O) -SO2-NH- C-NH ^ QN <N, SO 2 OCH, CH 3 0 CHr r ~ \ II N- <O) ~ SO2'NH "C" NH ~ 0) W NA Vso2 -CH3 SO2 CH3 'CH3 FORMULA 68 0 N-7 OCH./Q\_SO2- N H - C- N H - (Q \ <N- (, SO2 NCH3 CH3 CH3 FORMULA 69 0 OCHo (QySO2 - NH -C - NH - (Q \ N- (, so2 CH3 \ h3 OCH: FORMULA 70 0 CK O- SO2 "NH-C-NH - ( QN N- <^ so2 CH3 CH3 3 CH, FORMULA 71 0 0CH3 (QVso2-nh -c-nhh (0 / n N <.SO¬CH: CH3 CH3 FORMULA 72 OCH. II N ^ 3 (O) - SO2- NH - C-NH - (0 / NWN ^, SO2 CH3 CH3 OCH- FORMULA 67 FORMULA 73142 685 O CH- O- SC ^ -NH - C-NH-O N CH-. CH-. FORMULA U CH, 9 OCH, W (Q ^ SO2-NH- C-NH-O NA CH3 FORMULA 75 0 OCH-, O ^ SO ^ NH -C-NH-Hp ^ SO2 CH3 OCH3 FORMULA 76 3H3 U CHo / -a HW (P ^ SO2-NH-C-NH ^ O / N a N ~ \ -SO2 CH3 FORMULA 77 9 OCH- aa "W: ^ 3 ~ SO2-NH -C-NH - ^ T \ N Ko, N_ CH3 FORMULA 78 0 II N ^ X 7 * N ^ OCH- CH: 2 OCH- 0 CH- / _ II fW Q ^ -SO2-NH- C-NH- / V ~ NA SO-CH: CH3 CH-FORMULA 80 0 CH3 OCHo N4 i n-SO2-NH-C-NH- SO2 N CH3 CHo CH- FORMULA 81 OCH.II W 5 (OVSO2 -NH-C-NH-0; so2 OCH3 CH3 FORMULA 82 0 ChU II N ^ 3 XCH 3 CH-FORMULA 83 ON ^ .OCH.CH ^ SO2 OCH 3 3 CH3 FORMULA 84 O OCH3, _x II N ^ J CH ^ CH.ZÓR 79 WZtfR 85 £ 6 dQZ / V \ -HO eH ° KN er N HN-3-HN-CS II - O 96 dQZ / V \ 10 eH30 N (O) - HN-3-HN-c0S r N II eH30 ° H3 56 U0ZM eH3 £ H3 Q- HN-3 -HN -30S ^ Q • N || -H30 0 76 dC) ZM L6 yOZM £ H3 £ H3 £ H30 NO) - HN-3 -HN- 0S - rN 'H3 0 06 y H30 VN H30 HN-3- II 0 * HN- 68 dOZM £ H3 eH3 -2os- ^ j • £ H3 £ HC' H3 S ^ N Vn,} - ((O ^ HN-3 - HN - OS ^ O) Kn I I ^ 'H30 0 88 dQZM' H30 S ^ «J-HN-0 -HN-0S- (O) N II 'H00- £ 6 UCZM £ H0 S ^ Ul V- ((0 ~ HN-O-HN- 0S- (O): / "N II X— '' H30 O Z6 dOZM eH0Q nQ-hn-J? -Hn-ob- (0) ^ N 'y lH00 O' HO 'H0Q S' VN \ IQ- HN - 3 - HN - OS - (O) N '-H30 O LZ dQZM -HO' HO Vn no) "hn -3 - hn -zos- (o) ¦ / N II 'H30 o 98 dQZM £ H3 eH30. \ _N S b IO) "HN - 3 - HN -3OS - / ~ N 'H30 O 689 Ztl601 dOZM eHDO (\ 0 O-HN-3-HN-30S-Q £ / ~ N ii LH00 O eoi yoz / v \ LHO oA nQ) ~ hn-o-hn-os-O eHO T ^ N o 80i yoz / v \ "HO 'HOO O) yn 7) - ((O) - H N-0 - HN -OS-O . rn II -HOO O 201 dQZ / V \ £ H0 0 '^ HOO, 0 ^ Vn \ __ (- HNO-HN-Z0S ~ {0 - / N || ^ lH00 0 £ 0i yoz / v \ -H0 £ H0 O ^) O-HN-0-HN-30S ^ Q / —N II £ H0Q 0 901 dOZM £ H0 N HO O '(O) - HN ~ 0 - HN- 0S- (O Mi 11 xw / O' HO SOI doOZM £ H0O Vn NO) "HN-0 -HN-OS- / O) IOO O V0i dOZM eH0 'HO Nf) ^ HN-0-HN-2OS ^ P' HOO O 101 yozM 'HO, N £ H0 0 ^) 0 ~ HN - D - HN - 0S- 'HOO o 001 ygz / v \ eHO Vn (O) ~ HN-0-HN-0S- / ~ NH £ HO O 66 y © ZM -HO' HO VN (O) -HN-0 -HN-OS c / N "bH0O O 86 ^ OZM CH0, S HO 10 eH0 • HOO O 10 S89 Zfl142 685 O o NaH J-SQ, NH0? CftHn-OCO-CJHt- - ^ - - J- l L b b o b DMF SC ^ NHCOC6HE MODEL U MODEL 2 MODEL 2? HN-A I R FORMULA 3 A dioxane FORMULA SCHEME 1) HONO / HCL 2) S02CuCL2 / HOAc J-NH- FORMULA 6 J-SO2C FORMULA 5 NH ^ OH or NH3 FORMULA U SCHEME 2a) RV a OH | 2 | 3? Cl-C— OCH-R, and L NO2 K2C03 R '/ approx. 25 ° -80 ° C 1-10h RDR ~ R ~ 1 of 15 OC-OCH-R / 1 h N02 R'2 PATTERN approx. 150 ° - 300 ° C R1 MgCh catalyst u YC) FORMULA G "V_ ^" * ~ - ^ - ^ 1-24 hours O FORMULA H NH2 reduction FORMULA 6 a SCHEME 4 a) 1) S8 MODEL DU SO2NC (CH3) 3 MODEL CR ^ R ^ 2) CL-C- C = CH-R ^ A. 3) HCl b) FORMULA EA SLi SO ^ CH ^ I FORMULA D Rn Rn \ z 16 SC-OCH-A R "K2 SC ^ NHCtCH ^ FORMULA E c) FORMULA F SO2NHC (CH3) 3 FORMULA F CF3C02H 20 ° -60 ° 0.5 - 24 h SCHEME 3 SO2NH2 FORMULA U ao 00 en142 685 FORMAT 7 reagent FORMULA I FORMULA I reduction FORMULA 6b NHCCHo II J 0 FORMULA J FORMAT J deacetization SCHEME 6 1) diazotization ^ 1 «• 2) reagent FORMAT 9 MODEL K MODEL K reduction SCHEME 7 MODEL 6 d142 685 0 II NHCCH and UL OH MODEL 10 K2C03 Ri okoto 25 ^ 80 ° CR? Ro ir CL-CH —C = CHR / I 4 R2 'O NHCCHo? 2? 3 OCH— C = CHR / IR »MODEL LI) MgCL2 (catalyst) NH2 r okoto 150 ° - 300 ° R1 1 / O 2) deacetylation SCHEME 8 NBS 80 ° C 1-24 hours MODEL 11 MODEL M reflux 1-24 hours MODEL N reduction SCHEME142 685 N02 MODEL 12 R 10 O CLCH - C-Rn K2CO3 1-8h * approx. 25 ° -80 ° C RO ^, 0 U -OCH-CR NO. MODEL O 11 MODEL O 1) cyclization: ^ 2) reduction SCHEME 10 1) reagent »2) break up isomers 3) deacetylation of NH2 FORMULA 6g FORMULA 13 FORMULA 6h SCHEME 11 R N02 O OH FORMULA U 10 CI-CH-C-R11, K2C03 eye is 60 ° -80 ° C 1-8 hours O II OCH-C-Rn R10 MODEL P MODEL P cyclization 2) red FORMULA 6 and SCHEME 12142 685 R, HO R-.S NR- (NHZh) 2SO3, NH3 approx. 140 ° -180 ° C 10-30 hours R; H2N R-.S NR ~ FORMULA 15 FORMULA 6j SCHEME 13 R ', Ri R2 R3 Cl-C— C = CHR SH r »NH- NaOH 25 ° -.80 ° 1 -10 h Ri ^ T ^ SC— C- .-C — C = CHR PATTERN Q- 200 ° - 300 ° R '0.5-5 h PATTERN 6k SCHEME 14 6 stages PATTERN 16 PATTERN 61 SCHEME 15 142 685 PATTERN R PATTERN S., * ~ ~ PATTERN reduction - PATTERN 16 R ^^^ l "30% H 2 O 2 R1" "^^ okolfo 4P-90 ° C" RjO 0.5-3h. R1 MODEL T 5% Pd / weight? • woody d approx. 25 ° -40 ° C '1013 - 3039 hPa PATTERN U MODEL u ^ .HCL.CI ^ H »Ws approx. 50 ° -90 ° C - J ^ U 1- 3 hrs-S ^ R, Rr T 2 NH2 MODEL 6n SCHEME 17142 685 HoN N02 Rll 1) diazotization 2) reagent NO R, O 2 Rn S R10 FORMULA 18 MODEL V MODEL V SnCl2, HCl 0.5-3 hrs 25 ° -90 ° C NH? R, SCHEME 18 R10 0 rf ^ 1 d-CH-C-Rn K2CQ3i ^ R 0 nAA,, acetone, 25 ° -60 ° C. AAj "R, I SH R, T bCH-CR,. NO2 FORMULA 19 x1 NO2 PATTERN WZ0R w as polyphosphoric '^ Agh. Rl okolfo 75 ° -110 ° C PATTERN X PATTERN X SnCL2, HCl 0.5-3 hours 25 ° ~ 90 ° C SCHEME 19 MODEL Bpa) 142 685 NH Y-CN - FORMULA 20 HCl —- YC-OCH3 • HCL (FORMAT 21) -HCL b) FORMULA 21 H2NCN pH 5.5 NCN II YC-OCH3 FORMAT 22 O a) FORMULA 20 NH YN FORMULA 22 + X-C'-NH2— - h? n ^ O / NN \ X FORMULA 3f SCHEME 20 NaOCH3 CH3OH NH II Y- COCH ^ b) FORMULA 21 FORMULA 21 c) FORMULA 12 NH ^ Cl II —- YC-NH2-HCl FORMULA 23 NCN II XC-OCH3 - + MODEL 3f SCHEME 21142 685 XX ny HOCH2CH20K UM_5h (7 N "\ H NA 0 CH (OCHJ, CH'UN JZ O WZOR 3g PATTERN 3h SCHEME 22 XXN - ^ HNOo N- / H2N- <'NZ £ _ * Cl- nK hcl n <Y - Y PATTERN 24 PATTERN 25 X HoNR N- / PATTERN 25? RNH ^ '_ ZY FORMULATION 3 i SCHEME 23 NH l / i I ^ EtC-OCH2CH3 NN H9NCNHNHr HNOo —-—-—-—- H0N-C'j 2 2 pyridine 2 N ^ CH2CH3 SCHEME 2U CH3 yH / MU NM NC - N = C: N2H ^ "H2N- XOC2H5 CH3 SCHEME 25142 685 NH II H-NCNHNH.H HOCH2C02H * H2N ^ U CH2OH H 1) CS2 / 2) OH ~ H2N-« I SH SCHEME 26 H2NNH2 NC-N = C 7SCH3 H XSCH CH3CN 3 NN ': l — HoN-f I / SCH- NC-N = C. / OCH: H OCH 3 nn' CH3CN z NN * k OCH3 SCHEME 27 RV / NN xfjNh <2 CH3S Y20 ^ N-CN CH3CN N-N-X2 H2N OY2 SCHEME 28 PL

Claims (3)

Claims 1. A herbicide for controlling the growth of undesirable vegetation and regulating plant growth, comprising an active ingredient and at least one of a surfactant and a solid or liquid diluent, characterized in that the active ingredient is a compound of Formula 1, in which J is a group of formula 39, 40 or 41, and, Q is oxygen, sulfur or SO2, Qi is oxygen, sulfur, SO or SO2, R is hydrogen or methyl, R1 represents a hydrogen atom, a methoxy group, a methoxy group, a chlorine atom, a bromine atom, - the group NOa, CO2R8, SO2R6, OSO2R7 or. SOs1NRsRj1, Ra is a hydrogen atom or an alkyl group of 1-3 carbon atoms, R3 is a hydrogen atom or a methyl group, R4 is a hydrogen atom or a methyl group, R'4 is a hydrogen atom, a cMorium atom, a methyl group, a trifluoromethyl group, methoxyyl or atfpm, R5 is an alkyl group of 1-3 carbon atoms, CHtfCH = CH2, CH2CH3OCH3 or GH2OH4Cl, R6 is an alkyl group of 1-3 carbon atoms, R7 is an alkyl group of 1-3 carbon atoms or the trifluoromethyl group, Rs and R9 are independently of each other an alkyl group with 1-2 carbon atoms, Rio is a hydrogen, chlorine, bromine atom or an alkyl group with 1-3 carbon atoms, Rn is a hydrogen atom, a methyl group, a chlorine or bromine atom, W is oxygen or sulfur and A is a group of 42, 43, 44. 45 or 46, C is oxygen atom or CH2 group, X is hydrogen atom, methyl group, methoxy group or chlorine atom, Xi is methyl group, methoxy or ethoxyyl group, X2 is methyl, ethyl or CH2CF3 group * Y is methyl group , methoxy, ethoxy, CH2OCH3, NH2, NHCH2N / CHa'2, CH / OCH3 / 2, group of formula 47, ethyl, trifluorhethyl, CH2 = CHCH2O, SCH3, HC == CCHaO or CFsCIfeO, Y stands for ethyl, methyl, methoxy, epoxy, SCH3 or SCjHs, and Z stands for CH, nitrogen, OCH3, CO2H5, OQ or ORr, and their agriculturally acceptable salts, with the restriction that (1 ) in the groups of formulas 39 and 40, when Qi is oxygen and Ri is a substituent other than hydrogen, chlorine, bromo or NO *, then at least one of R2 and R3 is an alkyl group, and when Q1 is <* ork1, then Ri cannot be NO5, (2) in the group of formula 41, when Ri is NO2 or SO2 NRgRft, then R10 is an alkyl group of 1-3 carbon atoms, and Ru is a methyl group, (3) when X is a chlorine atom, then Z is CH, and Y is a meithoxy group, NH2, NHCH3, or N / OHWi, (4) when Qi is SO, then W is oxygen, and (5) when R'4 is a substituent other than hydrogen, then Ri is hydrogen. 2. Measure according to yzasitrz. 2. A process as claimed in claim 1, characterized in that the active ingredient is N-C / 4.6% neltyaicin, dihydro-2-methyl-7-benzenethiolenesulfionamide. 3. The measure according to claim 2. A process as claimed in claim 1, characterized in that the active ingredient is 1.1 ^ N- (4Nmeltxtoy ^ Hniety ^ ^ ^ methyl] ^ ^ 3HO ^ droH2Hme ^ yl ^ 7 ^ benzenethiophene sulfonamide. 4. The agent according to claim 1, characterized in that the active substance is N-4 / 4.6 ^ imeftoxyparine-tidinyl-2 ^ ^^^ hydro (only 6-74) enizene (thiophenesulfonamide). according to claim 1, characterized in that the active ingredient is 1,1-dioxide N-4/4 ^ H-dimieitylOH1, 3 ^ H2.3 ^ hydro ^ Hmethylp ^ Hbenizo ^ O (phen 6. The agent according to claim 1, characterized by the fact that it contains as active substance 1, 1, n-methoxy, H -methyl-3, 3, i5-itria ^ bonyflo] -2.3 Hdfinyide! TO ^ methyl-74) ^ ^ 5 amide. 1, characterized by the fact that the active substance is N-7 -dioxide. H [M, 6-dime {toc6yHl, 3, 5, tm -2, i3, iinydin, -neityl-7Hbe ^ 10 8. The agent according to claim 1, characterized in that the active substance is 2,3H-dihydroOHN - [/ 4-n-meitoxy-6-methylpyrimite-2 -Hmeitylbenzofuran-7-sulfonaimId. 9. The agent according to claim 1, characterized in that the active substance is Ni [(4,6-diimeltoxy-pyrimidinylH2 / anunocarbonyl] H2,3-dihydroH2-imethylbene isofuranoJ7nsulflonaniide. 10. The measure according to claim A compound as claimed in claim 1, characterized in that the active ingredient is N-4 / 4v6-Hdilrne4xfc n2,3-idihydlroibenzio [to] itiotphene, 7Hsullifonaniidii 11. The agent according to the present invention. 2. A compound as claimed in claim 1, characterized in that the active substance is 2,3- ihydro-4-hydroxide [i4-methoxy-methylpyrimidinyl-2 / - 25 aniinocaribonyio] ibenzo [ibJthioiphene-7HSuIphonamidf. 142 685 W II JSO NHCNA R Ry PATTERN ^ 3 O II SO9NHCN 'LI Cl NHR, PATTERN 26 R1HN- ^ n-SO-NHR2 H3C- PATTERN 29 R1 PATTERN 27 PATTERN 30 OCH: r, / 7 = \ II N - ^ CH ^ - S0oNH- C-NH ^ P) NWN ^ OCH 3 X H2N - ^ QZ FOR MODEL 3 a CH, FORMULA 28 Xl N H2N ^ nO O MODEL 3 d FORMULA 31 WR ^ SO ^ NH-C- NH-R MODEL 32 X • W MODEL 3b Xi X H- (H2N ^ Q NA Y MODEL 33 X N_y ^ Qn nK with MODEL 3c MODEL 3e MODEL 34 142 685 R3 R, R7 R5 MODEL 35 R8-Q 'R / R' R R. R: MODEL 39 Ri R, R2 Ql R3 XO / Z¬ NA Y PATTERN 42 Xl naJ PATTERN 36 R9 "PATTERN 37 PATTERN 38 Ri PATTERN 40 .R, 3 ^ —R, PATTERN 41 PATTERN 43 Xl PATTERN 44 R * V ^ iwx li - / ¦SCLNHCN- (Qz RN ^ R4 R1 Y X1 R3 R2 0 CH3 (Oz-SChNHCN-e I ^ = YIM * \ R * R, X- MODEL 47 R4 R3 R2 MODEL 45 * 2 R ¦ Y2 MODEL 49 \ Q] wx, W II N ^ 0-SO2NHCN <. RJ R, KG 4 1 MODEL 48 / MODEL R2, R3 QfVR4 W / 2H II WO ^ S02NHCN ^ Q / W 'Ni. Rt R MODEL 50 YL9 ypZM 89 dOZM £ H0V 20S ^ VN 7 M NO) - HN -3- HN - 0S ~ (O) T ^ N II ^ ^ H00 O 09 dOZM -HO, N W O-HN-3-HN-OS ^ O) 'HOO °. 6S dOZM £ H3 Z0S "^) (OyH N- 3- HN- OS- (Q. / Hd II ^ 'H30 O SS dOZM £ H0 £ H0 -HO O * .J)) ^ HN-0-HN-20S - (O c / NO 'H30 ys aoz / v \ £ H0 N £ HO £ HO' O '(OHN ^ HN- ° s-CJ N' HOO O £ S doOZM 'HOO HO HO o: yn. _ X 'HOO O ° HO C) ^ HN-3-HN-3OS ^ O e / N 1! - bHO O ZS dOZM' HO VN NO ^ HN- 0-HN-30S- (O / 'HO ^ O 9S yoz / v \ 'HOO ¦ £ HO £ HO O NO) - HN-0- HN-30S-O ^ N || XW / £ HOO • O 35 dC ^ £ H3 £ HO £ H3 O' OVHN-0-hN-20SyQ £ HO ° zD / - ^ HNZOS ^ QX. W La Oi d 689 Z? I142 685 OCH. / F * \ II N ~ (O ~ S0 -NH-C-NH-XO / N (SO9 N \ V / ^ J2 CH3 FORMULA 62 0 * CH-, <0-so2-nh-c-nh4q yso2 N \ CH: FORMULA 63 0 CH3 O-S0-NH-C-NH ^ Q Cso2 'n CH- 0CH3 FORMULA 64 0 OCH3 r ~ \ II N ^ QVS0 -NH-C-NH-O rnf NA \ ^ SO? OCH: CH- FORMULA 65 0 OCH3 -S00- NH - C -NH- (0 / N, SO. CH 3 CH- FORMULA 66 9 OCH. (O) -SO2-NH- C-NH ^ QN <N ^, SO2 OCH, CH3 0 CHr r ~ \ II N- <O) ~ SO2'NH "C" NH ~ 0) W NA Vso2 -CH3 SO2 CH3 'CH3 FORMULA 68 0 N-7 OCH. / Q \ _SO2- NH - C- NH - (Q \ <N- (, SO2 NCH3 CH3 CH3 FORMULA 69 0 OCHo (QySO2 - NH -C - NH - (Q \ N- (, so2 CH3 \ h3 OCH: FORMULA 70 0 CK O- SO2 "NH-C-NH - (QN N- <^ so 2 CH3 CH3 3 CH, FORMULA 71 OCH3 (QVso2-nh-c-nhh (0 / n N <SO CH: CH3 CH3 FORMULA 72 OCH. II N ^ 3 (O) - SO2- NH - C-NH - (0 / NWN ^, SO2 CH3 CH3 OCH- FORMULA 67 FORMULA 73142 685 O CH- O-SC ^ -NH - C-NH-O N CH- . CH-. FORMULA U CH, 9 OCH, W (Q ^ SO2-NH- C-NH-O NA CH3 FORMULA 75 0 OCH-, O ^ SO ^ NH-C-NH-Hp ^ SO2 CH3 OCH3 FORMULA 76 3H3 U CHo / -a HW (P 1 SO 2 -NH-C-NH 2 O / N a N ~ 1 -SO 2 CH 3 FORMULA 77 9 OCH- aa "W: ^ 3 -SO 2 -NH -C-NH - ^ T) N Ko, N_ CH3 FORMULA 78 0 II N ^ X 7 * N ^ OCH- CH: 2 OCH- 0 CH- / _ II fW Q ^ -SO2-NH-C-NH- / V ~ NA SO¬CH: CH3 CH-. FORMULA 80 0 CH3 OCHo N ^ i n-SO2-NH-C-NH- SO2 N CH3 CHo CH- FORMULA 81 OCH. II W 5 (OVSO2-NH-C-NH-0; so2 0CH3 CH3 FORMULA 82 0 ChU II N ^ 3 XCH 3 CH-. FORMULA 83 ON ^. CH CH ^ SO2 OCH 3 3 CH3 FORMULA 84 O OCH3, _x II N ^ J CH ^ CH. FORMULA 79 WZtfR 85 £ 6 dQZ / V \ -HO eH ° KN er N HN-3-HN-CS II - O 96 dQZ / V \ 10 eH30 N (O) - HN-3-HN-c0S r N II eH30 ° H3 56 U0ZM eH3 £ H3 Q- HN -3 -HN -30S ^ Q • N || -H30 0 76 dC) ZM L6 yOZM £ H3 £ H3 £ H30 NO) - HN-3 -HN- 0S- rN 'H3 0 06 y H30 VN H30 HN-3 - II 0 * HN- 68 dOZM £ H3 eH3 -2os- ^ j • £ H3 £ HC 'H3 S ^ N Vn,} - ((O ^ HN-3 - HN - OS ^ O) Kn II ^' H30 0 88 dQZM 'H30 S ^ «J-HN-0 -HN-0S- (O) N II 'H00- £ 6 UCZM £ H0 S ^ Ul V- ((0 ~ HN-O-HN-0S- (O): /" N II X - '' H30 O Z6 dOZM eH0Q nQ-hn-J? -Hn-ob- (0) ^ N 'y lH00 O' HO 'H0Q S' VN \ IQ- HN - 3 - HN - OS - (O) N '-H30 O LZ dQZM -HO' HO Vn no) "hn -3 - hn -zos- (o) ¦ / N II 'H30 o 98 dQZM £ H3 eH30. \ _N S b IO) "HN - 3 - HN -3OS - / ~ N 'H30 O 689 Ztl601 dOZM eHDO (\ 0 O-HN-3-HN-30S-Q £ / ~ N ii LH00 O eoi yoz / v \ LHO oA nQ) ~ hn-o-hn-os-O eHO T ^ N o 80i yoz / v \ "HO 'HOO O) yn 7) - ((O) - H N-0 - HN -OS-O . rn II -HOO O 201 dQZ / V \ £ H0 0 '^ HOO, 0 ^ Vn \ __ (- HNO-HN-Z0S ~ {0 - / N || ^ lH00 0 £ 0i yoz / v \ -H0 £ H0 O ^) O-HN-0-HN-30S ^ Q / —N II £ H0Q 0 901 dOZM £ H0 N HO O '(O) - HN ~ 0 - HN- 0S- (O Mi 11 xw / O' HO SOI doOZM £ H0O Vn NO) "HN-0 -HN-OS- / O) IOO O V0i dOZM eH0 'HO Nf) ^ HN-0-HN-2OS ^ P' HOO O 101 yozM 'HO, N £ H0 0 ^) 0 ~ HN - D - HN - 0S- 'HOO o 001 ygz / v \ eHO Vn (O) ~ HN-0-HN-0S- / ~ NH £ HO O 66 y © ZM -HO' HO VN (O) -HN-0 -HN-OS c / N "bH0O O 86 ^ OZM CH0, S HO 10 eH0 • HOO O 10 S89 Zfl142 685 O o NaH J-SQ, NH0? CftHn-OCO-CJHt- - ^ - - J- l L b b o b DMF SC ^ NHCOC6HE MODEL U MODEL 2 MODEL 2? HN-A I R FORMULA 3 A dioxane FORMULA SCHEME 1) HONO / HCL 2) S02CuCL2 / HOAc J-NH- FORMULA 6 J-SO2C FORMULA 5 NH ^ OH or NH3 FORMULA U SCHEME 2a) RV a OH | 2 | 3? Cl-C— OCH-R, and L NO2 K2CO3 R '/ approx. 25 ° -80 ° C 1-10hrs RDR ~ R ~ 1 of 15 OC-OCH-R / 1 h NO2 R'2 MODEL okoto 150 ° -300 ° C R1 MgCh catalyst u YC) MODEL G "V_ ^" * ~ - ^ - ^ 1-24 hours O FORMULA H NH2 reduction FORMULA 6 a SCHEME 4 a) 1) S8 FORMULA DU SO2NC (CH3) 3 FORMULA CR ^ R ^ 2) CL-C- C = CH-R ^ A. 3) HCl b) FORMULA EA SLi SO ^ CH ^ I FORMULA D Rn Rn \ z 16 SC-OCH-A R "K2 SC ^ NHCtCH ^ FORMULA E c) FORMULA F SO2NHC (CH3) 3 FORMULA F CF3C02H 20 ° -60 ° 0.5 - 24 hours SCHEME 3 S02NH2 FORMULA U ao 00 en142 685 FORMAT 7 reagent FORMULA I FORMULA I reduction FORMULA 6b NHCCHo II J 0 FORMULA J FORMULA J deacetization SCHEME 6 1) diazotization ^ 1 «• 2) reagent FORMAT 9 MODEL K MODEL K reduction SCHEME 7 MODEL 6 d142 685 0 II NHCCH and UL OH MODEL 10 K2C03 Ri okoto 25 ^ 80 ° CR? Ro ir CL-CH —C = CHR / I 4 R2 'O NHCCHo? 2? 3 OCH— C = CHR / IR »MODEL LI) MgCL2 (catalyst) NH2 r okoto 150 ° - 300 ° R1 1 / O 2) deacetylation SCHEME 8 NBS 80 ° C 1-24 hours MODEL 11 MODEL M reflux 1-24 hours MODEL N reduction SCHEME142 685 N02 MODEL 12 R 10 O CLCH - C-Rn K2CO3 1-8h * approx. 25 ° -80 ° C R. O ^, 0 U -OCH-CR NO. FORMULA O 11 MODEL O 1) cyclization: ^ 2 ) reduction SCHEME 10 1) reagent »2) break up isomers 3) deacetylation NH2 FORMULA 6g FORMULA 13 FORMULA 6h SCHEME 11 R N02 O OH FORMULA U 10 CI-CH-C-R11, K2C03 the eye is 60 ° -80 ° C 1- 8 hours O II OCH-C-Rn R10 MODEL P MODEL P cyclization 2) reduction PATTERN 6 and SCHEME 12142 685 R, HO R-. S NR- (NHZh) 2SO3, NH3 approx. 140 ° -180 ° C 10-30 hours R; H2N R-. S NR ~ FORMULA 15 FORMULA 6j SCHEME 13 R ', Ri R2 R3 Cl-C— C = CHR SH r »NH- NaOH 25 ° -.80 ° 1 -10 h Ri ^ T ^ S-C— C-. -C — C = CHR PATTERN Q- 200 ° - 300 ° R '0.5-5 h PATTERN 6k SCHEME 14 6 stages PATTERN 16 PATTERN 61 PATTERN 15 142 685 PATTERN R PATTERN S., * ~ ~ PATTERN reduction - M PATTERN 16 R ^^^ l "30% H 2 O 2 R1" "^^ okolfo 4P-90 ° C" RjO 0.5-3h. R1 MODEL T 5% Pd / weight? • woody d approx. 25 ° -40 ° C '1013 - 3039 hPa PATTERN U MODEL u ^ .HCL.CI ^ H »Ws approx. 50 ° -90 ° C - J ^ U 1- 3 hours -S ^ R, Rr T 2 NH2 MODEL 6n SCHEME 17142 685 HoN N02 Rll 1) diazotization 2) reagent NO R, O 2 Rn S R10 MODEL 18 MODEL V MODEL V SnCl2, HCl 0.5-3 hours 25 ° -90 ° C NH? R, SCHEME 18 R10 0 rf ^ 1 d-CH-C-Rn K2CQ3i ^ R 0 nAA,, acetone, 25 ° -60 ° C. AAj "R, I SH R, T bCH-CR ,. NO2 MODEL 19 x1 NO2 PATTERN WZ0R w as polyphosphoric '^ Agh. Rl okolfo 75 ° -110 ° C PATTERN X PATTERN X SnCL2, HCl 0.5-3 hours 25 ° ~ 90 ° C SCHEME 19 MODEL Bpa) 142 685 NH Y-CN - FORMULA 20 HCl —- YC-OCH3 • HCL (FORMAT 21) -HCL b) FORMULA 21 H2NCN pH 5.5 NCN II YC-OCH3 FORMAT 22 O a) FORMULA 20 NH YN FORMULA 22 + X-C'-NH2— - h? n ^ O / NN \ X FORMULA 3f SCHEME 20 NaOCH3 CH3OH NH II Y- COCH ^ b) FORMULA 21 FORMULA 21 c) FORMULA 12 NH ^ Cl II —- YC-NH2-HCl FORMULA 23 NCN II XC-OCH3 - + MODEL 3f SCHEME 21142 685 XX ny HOCH2CH20K UM_5h (7 N "\ H NA 0 CH (OCHJ, CH'UN JZ O WZOR 3g PATTERN 3h SCHEME 22 XXN - ^ HNOo N- / H2N- <'NZ £ _ * Cl - nK hcl n <Y - Y PATTERN 24 PATTERN 25 X HoNR N- / PATTERN 25? RNH ^ '_ ZY PATTERN 3 i SCHEME 23 NH l / i I ^ EtC-OCH2CH3 NN H9NCNHNHr HNOo —-—-—-—- H0N-C'j 2 2 pyridine 2 N ^ CH2CH3 SCHEME 2U CH3 yH / MU NM NC- N = C: N2H ^ "H2N- XOC2H5 CH3 SCHEME 25142 685 NH II H-NCNHNH. H HOCH2C02H * H2N ^ U CH2OH H 1 ) CS2 / 2) OH ~ H2N- «I SH SCHEME 26 H2NNH2 NC-N = C 7SCH3 H XSCH CH3CN 3 N-N ': 1 — HoN-f I / SCH-NC-N = C. / OCH: H OCH 3 n.n 'CH3CN with NN * k OCH3 SCHEME 27 RV / NN xfjNh <2 CH3S Y20 ^ N-CN CH3CN N-N-X2 H2N OY2 SCHEME 28 EN